DE102023135175A1 - Process for the preparation of amino acid esters and organic sulfonic acid salts as well as amino acid esters and their salts - Google Patents

Abstract

The present invention relates to an esteramine and its salt obtainable by a process comprising reacting alcohol, lactone and/or hydroxy acid, lactam and/or amino acid with acid, the process for synthesizing an esteramine and its salts, its organosulfate or - preferably - organosulfonate salts; such a reaction which comprises the step of reacting at least one component A (alcohol), at least one component B (lactone and/or hydroxy acid) and at least one component C (lactam and/or amino acid) in the presence of at least one component D (an acid), followed by optional removal of water and/or removal of excess alcohol, wherein the molar ratio of component C (lactam) to component D (acid) is within a range of 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1 and particularly preferably 1:1 to 1:1.08 and very particularly preferably about 1:0.5, i.e. exactly 1:1.05, and the molar ratio of component C (lactam) to the total number of hydroxy groups in component A (alcohol) is at most 1:1, preferably component C is less than equal to the total number of hydroxy groups in component A (alcohol), and the molar ratio of component B (Lactone/hydroxy acid) to the total number of hydroxy groups in component A (alcohol) is 1:0.1 to 1:10. Also included are the use of the esteramine and its salts as well as compositions containing them, in particular for the field of cleaning and detergents. Furthermore, methods for using such substances are included.

Description

The invention relates to a process for the synthesis of amino acid esters and their acid salts. The invention also relates to amino acid esters and their salts which are obtainable by such a process.

The esteramines and their salts obtainable or obtainable by a process according to the present invention can be used in specific compositions such as detergent, cleaning and/or fabric and household care compositions/formulations.

An advantage can be seen in the fact that the esteramines and their salts obtainable or obtained by a process according to the invention have improved clay dispersing properties and/or an improved whiteness compared to esteramines based, for example, on alkoxylated and non-alkoxylated diols and polyols of different structure, and in particular compared to known esteramines without sulfate or sulfonate groups.

In a further independent aspect, the esteramines and their salts obtainable or obtainable by a process according to the present invention exhibit improved biodegradability properties when used, for example, within cleaning agents.

Due to climate change, one of the most important objectives of the D&C industry today is to significantly reduce the CO2 emissions per wash cycle, for example by improving cold water conditions, improving cleaning efficiency at low temperatures below 40, 30 or 20 degrees or even colder, reducing the amount of chemicals used per wash cycle, increasing the weight efficiency of cleaning technologies, introducing bio-based components, etc. Therefore, a key objective of the D&C industry is the need for biodegradable ingredients to improve the sustainability of cleaning formulations (and especially laundry and dishwashing formulations) and avoid the accumulation of non-degradable compounds in the ecosystem. Therefore, there is a need to provide compounds that are biodegradable and yet have at least the same performance as already known but non-biodegradable compounds, as measured under defined conditions within 28 days, as required by many users, especially in the detergents sector, and as a future requirement by the current legislation in several countries and regions of the world.

Such a reduction in CO2 emissions or the desire to improve the "footprint" of a product generates a high and even increasing interest among industry and consumers, either in relation to its origin such as natural or renewable resources, or - all in comparison with previous products - its manufacture in terms of production efficiency and therefore reduced energy consumption, its efficiency in use, such as reduced quantities for the same performance or higher performance for the same quantity used, its persistence in the natural environment during and/or after its use, such as biodegradation.

As a consequence of these trends, there is a strong need for new biodegradable cleaning additives that offer at least comparable cleaning properties and a reduction of the carbon footprint by being bio-derived, biodegradable or even both. The materials should preferably have good primary cleaning activity, remove soil for oily/greasy and particulate stains and/or lead to improved whiteness retention, thus minimizing the amount of suspended and emulsified oily/greasy and particulate soils that redeposit on the surfaces of the textiles or hard surfaces, etc.

Knowledge of the state of the art

Organosulfate salts such as alkyl sulfate salts and alkyl ether sulfate salts are known as water-soluble salts used as cleaning agents or wetting agents.

Amino acid esters of amino acids with equal to or more than 3 carbon atoms can be synthesized from the corresponding lactams. This synthesis involves the ring opening of the lactam to obtain the amino acid in the presence of an acid as a first step and the esterification reaction with an alcohol as a second step.

FR2977585B1 discloses a process for the synthesis of α-amino acid esters of C7 to C36 alcohols from the amino acid or its salt in the presence of an acid catalyst, such as sulfuric acid in the presence of water, starting from amino acids or their salts.

WO2015172158 discloses salts of ethanesulfonic acid alpha and higher amino acid esters.

WO2011002746 discloses the production of amino acid esters with sulphuric acid

TRIVEDI, TJ et al. ChemSusChem 2011, Number 4, pages 604-608 describe a synthesis route to salts from alpha-C3-C4 amino acid esters and lauryl sulfate, which involves the formation of amino acid esters as hydrochloride salts followed by ion exchange with sodium lauryl sulfate.

SU1276661 discloses salts of protonated amino acid esters and anionic alkyl sulfates. They are obtained from amino acids with 2 moles of hexadecanol and excess sulfuric acid in dioxane.

JP49076822 and JP51036735 disclose a process for preparing amino acid ester salts with alkyl sulfates by heating 1 mole of amino acid with at least 3 moles of lauryl alcohol in the presence of sulfuric acid. The synthesis is carried out in toluene as solvent.

WO2019/007750 discloses alkoxylated esteramines and salts thereof, wherein the esteramine is derived from an alkoxylated monool, is reacted with an alpha-, beta- or higher amino acid, and the salt is formed by at least partial protonation of the amine group by an acid selected from the group consisting of methanesulfonic acid, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, citric acid and lactic acid. WO2019/007754 discloses similar structures except that these are derived from alkoxylated diols, oligools and polyols. Both disclose a similar process comprising reacting the alcohol with at least one alkylene oxide followed by at least partial esterification of the alkoxylated alcohol with at least one amino acid. Use is claimed in personal care applications and as a hardener for epoxy resins, as a reactant in the manufacture of polymers, in polyurethanes, polyureas or as thermoplastic polyamide adhesives.

The WO 2019/110371 discloses organic sulfonic acid salts of amino acid esters and a method of preparation. The method comprises the steps of reacting at least one lactam having at least 3 carbon atoms in the lactam ring with at least one organic sulfonic acid in an aqueous solution and then esterifying the reaction product with at least one alcohol having at least 8 carbon atoms and comprising at least one hydroxyl group, with optional removal of water after the second step; preferably both steps are carried out in a single step. Alcohols used can be all monoalcohols, diols, polyols, alkoxylated monoalcohols, alkoxylated diols and alkoxylated polyols. The molar ratio of organic sulfonic acid to lactam is in the range of 90 to 200 mol%.

WO2020/002162 discloses esteramine salts and a production process, wherein a monocarboxylic acid or an ester thereof is reacted with an amino alcohol and a sulfonic acid and the molar ratio of sulfonic acid to amino alcohol is greater than 1:1 [mol]/[mol]. The use is claimed in personal care applications and as a hardener for epoxy resins, as a reactant in the production of polymers, in polyurethanes, polyureas or as thermoplastic polyamide adhesives.

WO2020/144030 discloses a process for the synthesis of organosulfate salts of amino acid esters comprising the steps of (i) reacting at least one lactam having at least 3 carbon atoms in the lactam ring with sulfuric acid in an aqueous solution; (ii) esterifying the reaction product from step (i) with at least 200 mol% of at least one monoalcohol selected from the group consisting of linear alkyl alcohol containing a hydroxy group, branched alkyl alcohol containing a hydroxy group, linear alkyl alcohol containing a hydroxy group, branched alkyl ether alcohol containing a hydroxy group, phenoxyalkanols containing a hydroxy group, and mixtures thereof; (iii) optionally removing water and/or removing excess alcohol from step (ii). Preferably, steps (i) and (ii) are carried out in a single step. The counterion is an alkyl sulfate.

WO2022/002761 discloses sulfated esteramines obtainable by a process comprising step a): a) reacting at least one alcohol containing at least two hydroxy groups, which may be alkoxylated or non-alkoxylated, with at least one lactam and with sulfuric acid.

• Man erhält sie in einer mindestens zweistufigen Reaktionssequenz, wobei Mono- oder Polyole mit Lactonen oder Hydroxysäuren unter typischen Bedingungen für solche Polymerisationen oder Polykondensationen wie katalytische Mengen von Zinnkatalysatoren (Zinn(II)octoat etc.) umgesetzt werden. In einem zweiten Schritt werden die Hydroxyendgruppen der erhaltenen Polyester mit Aminosäuren verestert. Dies geschieht mit Methoden, die eine selektive Veresterung ermöglichen, wie z.B. die Verwendung geschützter Aminosäuren (Schutzgruppenchemie):
  • Solche Polymere aus Monoalkoholen wie MPEG sind in WO2014169403 ( US20150361219 ) und WO2016008401 beschrieben. Polymere auf der Basis von Diolen werden in WO2010055343 oder K. Nagahama et al., Chemistry Letters 2010, 39 (3); 250-251 . Polyole werden als Kernmaterialien in US20170056548 verwendet.
  • Die Polyester werden aus Lactonen wie Caprolacton oder Lactid oder aus Hydroxysäuren wie Milchsäure oder Glykolsäure synthetisiert. In US20150361219 erfolgt die Modifikation mit Aminosäuren mit Kondensationsmitteln wie Schwefelsäure, p-Toluolsulfonsäure usw. oder mit geschützten Aminogruppen in US20170056548 , gefolgt von der Entfernung der Schutzgruppe.

Polymers containing a polylactone or polyhydroxy acid block in combination with a terminal esteramine moiety are described in the literature:

• They are obtained in a reaction sequence of at least two stages, whereby mono- or polyols are reacted with lactones or hydroxy acids under typical conditions for such polymerizations or polycondensations, such as catalytic amounts of tin catalysts (tin(II) octoate, etc.). In a second step, the hydroxy end groups of the resulting polyesters are esterified with amino acids. This is done using methods that enable selective esterification, such as the use of protected amino acids (protecting group chemistry):
  • Such polymers of monoalcohols such as MPEG are in WO2014169403 ( US20150361219 ) and WO2016008401 Polymers based on diols are described in WO2010055343 or K. Nagahama et al., Chemistry Letters 2010, 39 (3); 250-251 . Polyols are used as core materials in US20170056548 used.
  • The polyesters are synthesized from lactones such as caprolactone or lactide or from hydroxy acids such as lactic acid or glycolic acid. In US20150361219 Modification with amino acids is carried out with condensing agents such as sulfuric acid, p-toluenesulfonic acid, etc. or with protected amino groups in US20170056548 , followed by removal of the protecting group.

It is known that caprolactone or 6-hydroxyhexanoic acid can be polymerized at hydroxy groups with catalytic amounts of Brönsted acids such as hydrochloric, sulfuric, phosphoric, methanesulfonic and p-toluenesulfonic acid ( N. Stanley et al., J. Polym. Sci. A: Polymer Chemistry 2014, 52, 2139-2145 ).

object

There is a continuing need for an improved process for producing sulfonate salts of amino acid esters in high yield with fast reaction times, without handling organic solvents, and without handling gaseous corrosive acids. There is also a need for a process for producing sulfonate salts of amino acid esters in a high yield reaction, thereby reducing reaction time and synthesis complexity.

There is a continuing need for amino acid ester salts that combine an amino acid ester active in detergent formulations with a sulfonate detergent for incorporation into improved detergent formulations for textile and home care applications such as hard surface cleaning and laundry.

It was an object of the present invention to provide esteramines and their salts and a process for their preparation which meet the goals and needs identified above.

This object has been achieved by the present invention as described below and as expressed in the claims.

It has now been found that a reaction of lactones or hydroxy acids with lactams or amino acids on structures containing hydroxy groups in the presence of equimolar amounts of Bronsted acids produces compounds which carry an oligo-/polylactone or oligo-/polyhydroxy acid block and an esteramine end group. The inclusion of an alcohol in this polymerization-like reaction means that the esteramines and their salts are the focus of this present invention.

In a one-step reaction, the reaction of a lactone or hydroxy acid and esterification of the hydroxy end group with amino acid is achieved when lactones or hydroxy acids are copolymerized with lactams or amino acids in the presence of stoichiometric amounts of acids relative to an amino acid or lactam. The inclusion of an alcohol in this reaction makes the esteramines and their salts the focus of this present invention.

Definitions

In this specification and in the following claims, unless the context otherwise requires, the word "comprise" and variations such as "comprises" and "comprising" are understood to imply the inclusion of a particular integer or step or group of integers or steps, but not the exclusion of any other integer or step or group of integers or steps. When used herein, the term "comprising" may be replaced by the term "containing" or "including," or sometimes when used herein, by the term "having."
When used herein, the term "consisting of" excludes any element, step, or component not specified in the claim element. When used herein, the term "consisting essentially of" does not exclude materials or steps that do not substantially affect the basic and novel features of the claim.

In any case herein, any of the terms "comprising,""consisting essentially of," and "consisting of" may be replaced with either of the other two terms. "Comprising" may be replaced with "consisting essentially of" in a preferred embodiment, and both may be replaced with "consisting of" in an even more preferred embodiment.
The compositions of the present disclosure may "comprise" (ie contain other constituents), "consist essentially of constituents" (contain mainly or almost only the constituents mentioned and other constituents in only very small amounts, mainly only as impurities) or "consist of" (ie contain only the constituents mentioned and furthermore contain only impurities that are unavoidable in a technical environment, preferably only the constituents) the constituents of the present disclosure.
Similarly, the terms "substantially free of..." or "substantially free of..." or "(containing/comprising) substantially no..." may be used herein; this means that the specified material is at least not intentionally added to the composition to be a part of it, or, preferably, is not present in analytically detectable amounts. It is intended to include compositions in which the specified material is present only as an impurity in one of the other intentionally included materials. The specified material may be present, if at all, at a level of less than 1%, or even less than 0.1%, or even less than 0.01%, or even 0% by weight of the composition.

In general, as used herein, the term "obtainable by" means that corresponding products do not necessarily have to be made (i.e., obtained) by the corresponding process or method described in the respective specific context, but also includes products having all the characteristics of a product made (obtained) by the corresponding process or method, wherein the products are not actually made (obtained) by such a process or method. However, the term "obtainable by" also includes the more restrictive term "obtained by," i.e., products actually made (obtained) by a process or method described in the respective specific context.

When a definition is used herein that requires a compound or substituent of a compound to consist of "at least a number of carbon atoms," the number of carbon atoms refers to the total number of carbon atoms in the compound or substituent of a compound. For example, for a substituent disclosed as "alkyl ethers having at least 8 carbon atoms comprising alkylene oxide groups," the total number of at least 8 carbon atoms must be the sum of the number of carbon atoms of the alkyl portion and the number of carbon atoms of the alkylene oxide units.
All these terms, which are not specifically defined, have their ordinary meaning as known in the field of organic chemistry.

The term "containing a hydroxy group" means that only one -OH group is present. Any functionalized group derived from a hydroxy group, such as an ether group, is not considered an -OH group.

The term "containing at least two hydroxy groups" means that two or more -OH groups are present. The term "hydroxy group" is synonymous with the term "hydroxyl group" or "-OH group". Alcohols/compounds that have only one hydroxy group, such as methanol or ethanol, therefore do not fall under the definition of an alcohol that contains at least two hydroxy groups according to the Compound (A) of the present invention. Any functionalized group derived from a hydroxy group, such as an ether group, is not considered to be an -OH group.

As used herein, the articles "a" and "an," when used in a claim or embodiment, are understood to mean one or more of the elements claimed or described. As used herein, the terms "include" and "including" are not intended to be limiting and therefore encompass more than the specific subject matter mentioned after those words.

The term "approximately" as used herein includes the exact number "X", e.g. mentioned as "about X%", etc., and small variations of X, including from minus 5 to plus 5% deviation from X (with X set to 100% for this calculation), preferably from minus 2 to plus 2%, more preferably from minus 1 to plus 1%, even more preferably from minus 0.5 to plus 0.5%, and smaller deviations. Of course, if the given value X itself is already "100%" (such as for purity, etc.), then the term "approximately" can and clearly means only deviations therefrom that are smaller than "100".

The term "anhydrous" means that the composition contains no more than 5% by weight of water based on the total amount of solvent, in another embodiment no more than 1% by weight of water based on the total amount of solvent, in another embodiment contains no water at all.

All temperatures reported herein are in degrees Celsius (°C) unless otherwise specified. Unless otherwise noted, all measurements are made at 20°C and under atmospheric pressure. In all embodiments of the present disclosure, all percentages are by weight of the total composition unless expressly stated otherwise. All ratios are by weight unless expressly stated otherwise.

The term "fabric care composition" is intended to encompass compositions and formulations designed for the treatment of textiles. Such compositions include, but are not limited to, laundry cleaning and detergent compositions, softening compositions, fabric improvers, fabric fresheners, laundry prewash, laundry pretreatment, laundry additives, spray products, chemical cleaning agents or compositions, laundry rinse additive, laundry additive, post-rinse fabric treatment, ironing aid, unit dose formulation, delayed delivery formulation, laundry detergent, laundry detergent contained on or in a porous substrate or nonwoven film, and other suitable forms that may be apparent to one of ordinary skill in the art in view of the teachings contained herein and described herein below in describing the compositions. Such compositions may be used as a prewash treatment, as a postwash treatment, or added during the rinse or wash cycle of the laundry process, and as described further herein when describing the use and application of the esteramine and its salts of the present invention.

“Sulfonates” in the sense of the present invention are the anions derived from sulfonic acids, preferably alkanesulfonic acid and/or arylsulfonic acid, particularly preferably alkanesulfonic acid, very particularly preferably methanesulfonic acid; Such acids are used to at least partially protonate the esteramines and thus form the sulfonates of the esteramines.

In this specification, the term "inventive compound" may be used instead of "inventive esteramines and/or their salts" and "esteramine(s) and/or their salt(s) of this (present) invention", which means that those compounds disclosed herein as being inventive are defined by their structure and/or method of preparing them or obtaining them by the method defined herein.

Detailed description

The definitions and their preferences set forth in the previous “Definition” section are included as part of this invention as described herein below.

The specific embodiments as described in this disclosure are included in the present invention as part of this invention; the various other options which are designated in this present description as "optional", "preferred", "more preferred", "even more preferred" or "most preferred" are most preferred" (or "preferred", etc.) may be selected individually and independently of one another (unless such independent selection is not possible due to the nature of that feature or when such independent selection is expressly excluded) and then combined within any of the other embodiments (other such options and preferences may also be selected individually and independently, unless such independent selection is not possible due to the nature of that feature or when such independent selection is expressly excluded), each and all such possible combinations being included as part of this invention as individual embodiments.

Compound: Esteramines and their salts

1. (A) mindestens einen Alkohol, der mindestens eine Hydroxygruppe trägt, wobei gegebenenfalls mindestens eine Hydroxygruppe in einem Schritt vor Schritt a) mit mindestens einem Alkylenoxid, bevorzugt mindestens 1 und bis zu 200, bevorzugt 1 bis 100, besonders bevorzugt bis zu 50 Mol Alkylenoxid pro Hydroxygruppe alkoxyliert werden kann,
2. (B) mindestens ein Lacton und/oder (bevorzugt oder) Hydroxysäure, besonders bevorzugt nur Lacton,
3. (C) mit mindestens einem Lactam und/oder (bevorzugt oder) mindestens einer Aminosäure, besonders bevorzugt nur Lactam, und
4. (D) eine anorganische oder organische Säure, wobei die organische oder anorganische Säure vorzugsweise einen pKa-Wert im Bereich von -3 und bis +5, besonders bevorzugt von -2,5 bis 1,5 aufweist, bevorzugt organische Säure, besonders bevorzugt Sulfonsäuren, noch mehr bevorzugt Alkansulfonsäure und/oder Arylsulfonsäure, besonders bevorzugt Alkansulfonsäure, ganz besonders bevorzugt Methansulfonsäure,

worin das molare Verhältnis von
Komponente C (Lactam) bis Komponente D (Säure) in einem Bereich von 1:0,9 bis 1:1,5, bevorzugt etwa 1:0,95 bis 1:1,1 und besonders bevorzugt 1:1 bis 1:1,08 und ganz besonders bevorzugt etwa 1:1,02 wie genau 1:1,02 liegt, und
Komponente C (Lactam) pro Hydroxygruppe in Komponente A (Alkohol) höchstens 1:1, vorzugsweise Komponente C kleiner als gleich pro Hydroxygruppe in Komponente A (Alkohol), und Komponente B (Lacton/Hydroxysäure) pro Hydroxygruppe in Komponente A (Alkohol) von 1:0,1 bis 1:10.The present invention relates to esteramines and their salts obtainable by a process comprising the step of reacting A + B + C in the presence of D with

1. (A) at least one alcohol which carries at least one hydroxyl group, where optionally at least one hydroxyl group can be alkoxylated in a step before step a) with at least one alkylene oxide, preferably at least 1 and up to 200, preferably 1 to 100, particularly preferably up to 50 mol of alkylene oxide per hydroxyl group,
2. (B) at least one lactone and/or (preferably or) hydroxy acid, particularly preferably only lactone,
3. (C) with at least one lactam and/or (preferably or) at least one amino acid, particularly preferably only lactam, and
4. (D) an inorganic or organic acid, wherein the organic or inorganic acid preferably has a pKa value in the range from -3 to +5, particularly preferably from -2.5 to 1.5, preferably organic acid, particularly preferably sulfonic acids, even more preferably alkanesulfonic acid and/or arylsulfonic acid, particularly preferably alkanesulfonic acid, very particularly preferably methanesulfonic acid,

where the molar ratio of
Component C (lactam) to component D (acid) in a range of 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1 and particularly preferably 1:1 to 1:1.08 and most preferably about 1:1.02, such as exactly 1:1.02, and
Component C (lactam) per hydroxy group in component A (alcohol) at most 1:1, preferably component C less than or equal to per hydroxy group in component A (alcohol), and component B (lactone/hydroxy acid) per hydroxy group in component A (alcohol) from 1:0.1 to 1:10.

1. (A) mindestens einen Alkohol, der mindestens eine Hydroxygruppe trägt, wobei gegebenenfalls mindestens eine Hydroxygruppe in einem Schritt vor Schritt a) mit mindestens einem Alkylenoxid, bevorzugt mindestens 1 und bis zu 200, bevorzugt 1 bis 100, besonders bevorzugt bis zu 50 Mol Alkylenoxid pro Hydroxygruppe alkoxyliert werden kann,
2. (B) mindestens ein Lacton und/oder (bevorzugt oder) Hydroxysäure, besonders bevorzugt nur Lacton,
3. (C) mit mindestens einem Lactam und/oder (bevorzugt oder) mindestens einer Aminosäure, besonders bevorzugt nur Lactam, und
4. (D) eine anorganische oder organische Säure, wobei die organische oder anorganische Säure vorzugsweise einen pKa-Wert im Bereich von -3 und bis +5, besonders bevorzugt von -2,5 bis 1,5 aufweist, bevorzugt organische Säure, besonders bevorzugt Sulfonsäuren, noch mehr bevorzugt Alkansulfonsäure und/oder Arylsulfonsäure, besonders bevorzugt Alkansulfonsäure, ganz besonders bevorzugt Methansulfonsäure,

wobei die Verbindungen A, B, C und D in einem molaren Verhältnis OH (der Alkoholkomponente A) : B (Lacton/Hydroxysäure) : C (Lactam/Aminosäure): D (Säure) eingesetzt werden, die (1 : (0,1 - 10, vorzugsweise 0,1 - 5) : (0,1 - 1) : (0,1 - 1,5) ist.In an alternative embodiment, the invention relates to esteramines and their salts obtainable by a process comprising the step of reacting A + B + C in the presence of D with

1. (A) at least one alcohol which carries at least one hydroxyl group, where optionally at least one hydroxyl group can be alkoxylated in a step before step a) with at least one alkylene oxide, preferably at least 1 and up to 200, preferably 1 to 100, particularly preferably up to 50 mol of alkylene oxide per hydroxyl group,
2. (B) at least one lactone and/or (preferably or) hydroxy acid, particularly preferably only lactone,
3. (C) with at least one lactam and/or (preferably or) at least one amino acid, particularly preferably only lactam, and
4. (D) an inorganic or organic acid, wherein the organic or inorganic acid preferably has a pKa value in the range from -3 to +5, particularly preferably from -2.5 to 1.5, preferably organic acid, particularly preferably sulfonic acids, even more preferably alkanesulfonic acid and/or arylsulfonic acid, particularly preferably alkanesulfonic acid, very particularly preferably methanesulfonic acid,

wherein the compounds A, B, C and D are used in a molar ratio OH (of the alcohol component A) : B (lactone/hydroxy acid) : C (lactam/amino acid) : D (acid) which is (1 : (0.1 - 10, preferably 0.1 - 5) : (0.1 - 1) : (0.1 - 1.5).

Alcohols containing one hydroxy group are well known in the art. Similarly, alcohols containing at least two hydroxy groups according to compound (A) are known to the person skilled in the art. As mentioned above, the respective alcohol can contain one, two, three, four, five or even more hydroxy groups within the respective molecule/compound. The respective alcohol can contain linear, branched and/or cyclic alkyl fragments. In addition, the respective alcohol can also contain aromatic fragments and combinations of alkyl and aromatic fragments ("aralkyl" fragments). Furthermore, the respective alcohol can also contain alkyl ether fragments. Examples of alcohols according to compound (A) are glycerin, pentaerythritol, sorbitol, 1,1,1-trimethylolpropane (TMP), erythritol or alkoxylated alcohols, such as polyethylene glycol.
Many alcohols according to compound (A) of the present invention are commercially available, for example under the trade name “Pluronic(s)” or “Pluriol” (e.g. as polyethylene glycol block (co)polymers) from BASF SE.

• (Aa) Monoalkohole wie C1- bis C36-Alkanole, ausgewählt aus den Gruppen der nicht-alkoxylierten linearen C2- bis C36-Alkohole, wie Mischungen solcher Alkohole ausgewählt aus C6-bis C22-Fettalkoholen, bevorzugt C8- bis C22-Fettalkoholen, besonders bevorzugt C12- und C14-Fettalkoholen, ganz besonders bevorzugt C16- und C18-Fettalkoholen; nicht alkoxylierte verzweigte C3- bis C36-Alkohole wie 2-Ethylhexanol, 2-Propylheptanol, Isotridecanol, Isononanol, C9-C17-Oxoalkohole; alkoxylierte lineare C2- bis C36-Alkohole wie alkoxylierte Mischungen von C6- bis C22-Fettalkoholen, bevorzugt alkoxylierte Mischungen von C8- bis C22-Fettalkoholen, besonders bevorzugt alkoxylierte Mischungen von C12- und C14-Fettalkoholen, ganz besonders bevorzugt alkoxylierte Mischungen von C16- und C18-Fettalkoholen; alkoxylierte verzweigte C3- bis C36-Alkohole wie alkoxyliertes 2-Ethylhexanol, alkoxyliertes 2-Propylheptanol, alkoxyliertes Isotridecanol, alkoxyliertes Isononanol, alkoxylierte C9-C17-Oxoalkohole;
• (Ab) Dialkohole wie Alkandiole, polyalkoxylierte C2-C6-Alkandiole mit mindestens zwei Hydroxygruppen,
• (Ac) Oligoalkohole wie Zuckeralkohole, polyalkoxylierte Zuckeralkohole, C3-C6-Alkantriole, polyalkoxylierte C3-C6-Alkantriole mit mindestens drei Hydroxygruppen,
• (Ad) Polyole wie C5-C6-Alkanpolyole, polyalkoxylierte C5-C6-Alkanpolyole, Polyetherole wie Polyglycerin oder Di- oder Tripentaerythrit, alkoxylierte Polyetherole wie alkoxyliertes Polyglycerin, alkoxylierter Di- oder Tripentaerythrit,
• (Ae) Phenoxyalkanole, wie Phenoxyethanol;

mit den Alkoholen bevorzugt ausgewählt aus der Gruppe Aa) der Monoalkohole und/oder Ab) alkoxylierten Di-, Oligo- und Polyolalkoholen, und den Alkoholen besonders bevorzugt ausgewählt aus der Gruppe der Monoalkohole und alkoxylierten Dialkohole.The alcohol (A) for the esteramine according to the invention and the process according to the invention as described herein is selected from

• (Aa) monoalcohols such as C1 to C36 alkanols, selected from the groups of non-alkoxylated linear C2 to C36 alcohols, such as mixtures of such alcohols selected from C6 to C22 fatty alcohols, preferably C8 to C22 fatty alcohols, particularly preferably C12 and C14 fatty alcohols, very particularly preferably C16 and C18 fatty alcohols; non-alkoxylated branched C3 to C36 alcohols such as 2-ethylhexanol, 2-propylheptanol, isotridecanol, isononanol, C9-C17 oxo alcohols; alkoxylated linear C2 to C36 alcohols such as alkoxylated mixtures of C6 to C22 fatty alcohols, preferably alkoxylated mixtures of C8 to C22 fatty alcohols, particularly preferably alkoxylated mixtures of C12 and C14 fatty alcohols, very particularly preferably alkoxylated mixtures of C16 and C18 fatty alcohols; alkoxylated branched C3 to C36 alcohols such as alkoxylated 2-ethylhexanol, alkoxylated 2-propylheptanol, alkoxylated isotridecanol, alkoxylated isononanol, alkoxylated C9-C17 oxo alcohols;
• (Ab) dialcohols such as alkanediols, polyalkoxylated C2-C6 alkanediols with at least two hydroxy groups,
• (Ac) Oligoalcohols such as sugar alcohols, polyalkoxylated sugar alcohols, C3-C6 alkanetriols, polyalkoxylated C3-C6 alkanetriols with at least three hydroxy groups,
• (Ad) Polyols such as C5-C6 alkane polyols, polyalkoxylated C5-C6 alkane polyols, polyetherols such as polyglycerol or di- or tripentaerythritol, alkoxylated polyetherols such as alkoxylated polyglycerol, alkoxylated di- or tripentaerythritol,
• (Ae) Phenoxyalkanols, such as phenoxyethanol;

with the alcohols preferably selected from the group Aa) of monoalcohols and/or Ab) alkoxylated di-, oligo- and polyol alcohols, and the alcohols particularly preferably selected from the group of monoalcohols and alkoxylated dialcohols.

In a more preferred embodiment, the alcohol (A) used for the esteramine and process of the invention is an alkoxylated alcohol obtained by alkoxylating at least one hydroxy group of the alcohol of claim 2 with one or more alkylene oxides to produce alkyleneoxy chains comprising one or more units selected from alkylene oxides selected from C2 to C22 alkylene oxides, preferably C2-C4 alkylene oxides, wherein the units derived from the alkylene oxide(s) may be arranged in random, block or multi-block order or combinations thereof, preferably as block.

Alkoxylation of the alcohol can be achieved by either carrying out the alkoxylation reaction with only one alkylene oxide or with more than one alkylene oxide. When more than one alkylene oxide is used, the resulting alkyl ether alcohols comprise either randomly distributed alkylene oxide units, or a block of one alkylene oxide followed by a block of another alkylene oxide, or a block of one alkylene oxide followed by another block comprising two or more alkylene oxides arranged in random order, or a block comprising two or more alkylene oxides followed by another block comprising two or more alkylene oxides, each of these blocks differing in their relative amount of alkylene oxides, their arrangement of alkylene oxides and/or the identity of the alkylene oxides, such that two interconnected blocks differ in their chemical composition and arrangement; any such combination of arrangements is in principle possible and as such is encompassed by the present invention.
In one embodiment of the present invention, alkyl alcohols alkoxylated with only a single alkylene oxide are used. In another embodiment, alkyl alcohols alkoxylated with a first alkylene oxide are used, followed by alkoxylation with a second alkylene oxide, thereby forming a block structure of various alkylene oxide blocks.
In the context of the present invention, it is also preferred that, if the compound (A) comprises an alkoxylated alcohol, the alkoxylated fragment comprises at least one C2-C22 alkylene oxide, preferably C2-C4 alkylene oxides, particularly preferably ethylene oxide and/or propylene oxide, very particularly preferably the respective alcohol comprises at least one block based on ethylene oxide and/or propylene oxide, and even more preferably contains only one block consisting of ethylene oxide or consisting of two blocks, the first block - preferably the "inner block" directly linked to the hydroxy group of the alcohol - consisting of ethylene oxide and a second block - preferably the "outer block linked to the ethylene oxide block - consisting of propylene oxide.

1. i) Lacton(e), d. h. cyclische Ester, beginnend mit α-Lacton (drei Ringatome), gefolgt von β-Lacton (vier Ringatome), γ-Lacton (fünf Ringatome) usw.; solche Lactone sind vorzugsweise β-Propiolacton, g-Butyrolacton, δ-Valerolalacton, g-Valerolalacton, e-Caprolacton, d-Decalacton, g-Decalacton, e-Decalacton; vorzugsweise Caprolacton; und
2. ii) Hydroxysäure(n), die sich durch Hydrolyse von jedem Lacton ableiten kann, insbesondere von einem beliebigen Lacton innerhalb der Gruppe i) vor, insbesondere eine α-, β- oder γ-Hydroxysäure, die durch Hydrolyse von dem entsprechenden Lacton abgeleitet ist, und Milchsäure, Glykolsäure, 4-Hydroxybutansäure, 6-Hydroxyhexansäure, 12-Hydroxystearinsäure, Zitronensäure; Bevorzugt Milchsäure oder Caprolacton, besonders bevorzugt Caprolacton.

The at least one lactone and/or hydroxy acid (compound B) for the esteramine according to the invention and its salts and the process according to the invention is selected from groups i) and/or ii), with

1. i) Lactone(s), ie cyclic esters starting with α-lactone (three ring atoms), followed by β-lactone (four ring atoms), γ-lactone (five ring atoms), etc.; such lactones are preferably β-propiolactone, g-butyrolactone, δ-valerolalactone, g-valerolalactone, e-caprolactone, d-decalactone, g-decalactone, e-decalactone; preferably caprolactone; and
2. ii) hydroxy acid(s) which can be derived by hydrolysis from any lactone, in particular from any lactone within group i), in particular an α-, β- or γ-hydroxy acid derived by hydrolysis from the corresponding lactone, and lactic acid, glycolic acid, 4-hydroxybutanoic acid, 6-hydroxyhexanoic acid, 12-hydroxystearic acid, citric acid; preferably lactic acid or caprolactone, particularly preferably caprolactone.

Lactams are cyclic amides, starting with alpha-lactam (three ring atoms), followed by beta-lactam (four ring atoms), gamma-lactam (five ring atoms), and so on. Upon hydrolysis, lactams form the corresponding alpha, beta, and gamma amino acids.
All lactams having at least three carbon atoms in the lactam ring can be used in the present invention as compounds C. In one embodiment of the present invention, lactams having four to twelve carbon atoms in the lactam ring are used.
In another preferred embodiment of the present invention, lactams having five to seven carbon atoms in the lactam ring are used. In another, even more preferred embodiment, a lactam having six carbon atoms in the lactam ring, epsilon-lactam, is used.

More specifically, the at least one lactam or amino acid (C) for the esteramine and salts thereof and the process according to the invention is selected from lactams which are cyclic amides starting with alpha-lactam (three ring atoms), followed by beta-lactam (four ring atoms), gamma-lactam (five ring atoms) and so on, such as epsilon-caprolactam, gamma-butyrolactam, piparidone, laurolactam, N-methylpyrrolidone; and the corresponding alpha-, beta-, gamma-amino acids, etc., which can be obtained from the lactams by hydrolysis, and alpha-amino acids such as alanine, glycine, leucine, isoleucine, valine, proline, phenylalanine, arginine, asparagine, aspartic acid, aspartate, glutamine, glutamate, histidine, lysine, threonine, tryptophan, tyrosine, cysteine, methionine, serine; alpha-amino acids with secondary or tertiary amino groups such as sarcosine, N,N-dimethylglycine; other amino acids such as 6-aminohexanoic acid, 4-aminobutanoic acid, 3-aminopropanoic acid, 12-aminododecanoic acid, 11-aminoundecanoic acid;
preferably alanine, 6-aminohexanoic acid, 4-aminobutyric acid, lactic acid and caprolactam, particularly preferably lactic acid and/or epsilon-caprolactam, very particularly preferably epsilon-caprolactam.

1. i) Alkylsulfonsäuren, wie Methansulfonsäure, Ethylsulfonsäure, Propylsulfonsäure, Kampfersulfonsäure; Alkylarylsulfonsäuren und insbesondere Alkylbenzolsulfonsäuren, wie Toluolsulfonsäure (einschließlich ihres Isomerengemisches), p-Toluolsulfonsäure, o-Toluolsulfonsäure, m-Toluolsulfonsäure, Xylolsulfonsäure (Isomerengemisch), 2 ,6-Dimethylbenzolsulfonsäure, 2 ,5-Dimethylbenzolsulfonsäure, 2 ,4-Dimethylbenzolsulfonsäure, 4-Dodecylbenzolsulfonsäure, iso-Propylbenzolsulfonsäure, Ethylbenzolsulfonsäure und Naphthalinsulfonsäure, und
2. ii) anorganische Säuren wie Schwefelsäure, Salzsäure, Bromwasserstoffsäure, Phosphorsäure; vorzugsweise Schwefelsäure; bevorzugt eine Säure ausgewählt aus Gruppe i), besonders bevorzugt para-Toluolsulfonsäure und/oder Methansulfonsäure, ganz besonders bevorzugt Methansulfonsäure.

The acid (D) for the esteramine according to the invention and its salts and the process according to the invention is selected from

1. (i) alkylsulfonic acids, such as methanesulfonic acid, ethylsulfonic acid, propylsulfonic acid, camphorsulfonic acid; alkylarylsulfonic acids and in particular alkylbenzenesulfonic acids, such as toluenesulfonic acid (including its isomer mixture), p-toluenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, xylenesulfonic acid (isomer mixture), 2,6-dimethylbenzenesulfonic acid, 2,5-dimethylbenzenesulfonic acid, 2,4-dimethylbenzenesulfonic acid, 4-dodecylbenzenesulfonic acid, isopropylbenzenesulfonic acid, ethylbenzenesulfonic acid and naphthalenesulfonic acid, and
2. (ii) inorganic acids such as sulphuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid; preferably sulphuric acid; preferably an acid selected from group i), particularly preferably para-toluenesulfonic acid and/or methanesulfonic acid, very particularly preferably methanesulfonic acid.

In an alternative preferred embodiment for the esteramine according to the invention and the process according to the invention, sulfuric acid is used as acid (D). The result is then the esteramine as an at least partially sulfated esteramine salt, since the sulfuric acid not only at least partially protonates the esteramine, but also at least partially sulfates the hydroxy groups of the monoalcohol or di- and polyol.

Depending on the acid used, the esteramine is obtained as an at least partially protonated salt in cationic or zwitterionic form if a di- or polyol is used. If sulfuric acid is used, the resulting esteramine is sulfated and thus the sulfated esteramine is obtained in zwitterionic form. With the other acids besides sulfuric acid, the esteramine is obtained as an at least partially protonated esteramine and thus in cationic form.
In the case of a monoalcohol, the use of sulfuric acid yields the esteramine as at least partially protonated esteramine and a sulfated monoalcohol counterion.

In a preferred embodiment, the esteramine is obtained when the compounds A, B, C and D are in a molar ratio OH (of the alcohol component A) : B (lactone/hydroxy acid) : C (lactam/amino acid) : D (acid) which is (1) : (0.1 - 10, preferably 0.1 - 5) : (0.1 - 1) : (0.1 - 1.5); All combinations of the individual numbers in the preceding ratio are explicitly part of this invention, i.e. any number of the ranges can be selected individually to arrive at a certain defined overall ratio of A:B:C:D.
For the avoidance of doubt, if the alcohol component A contains more than one hydroxy group, the “OH number” (hydroxy number) refers to each hydroxy group in the ratio given above

In a preferred embodiment, the esteramine according to any of the preceding embodiments has a structure consisting of a first alcohol-resulting "block" (X) bearing one or more hydroxy groups, of which at least one hydroxy group is linked via an ester function to a second block (Y) resulting from a single lactone or an oligo- or polyester block, and a third block (Z) resulting from the addition of an amino acid or a lactam to such a second block, so that the esteramine has the structure "XYZ" or "X(Y)nZ", where n are integers from 1 to 10 when the alcohol (A) is a monoalcohol (from group Aa), while n can be any number from 0.1 to 10 for the esteramine when the alcohol (A) used is selected from groups (Ab), (Ac) and/or (Ad) as defined hereinbefore.

mit

R

Monoalkohol, Di- oder Polyol, gegebenenfalls alkoxyliert

o

0,1 bis 10 (und jede Zahl und Dezimalzahl dazwischen)

p

0,1-1 (und jede Zahl und Dezimalzahl dazwischen)

n

1-13

m

1-13

R1, R2

Wasserstoff oder C1-C6-Alkyl (linear oder verzweigt)

R3, R4

Wasserstoff oder C1-C6-Alkyl linear oder verzweigt) oder Phenyl.

The structures of the esteramines according to the invention can be represented in formula (I) as follows:

with

R

Monoalcohol, di- or polyol, optionally alkoxylated

O

0.1 to 10 (and every number and decimal in between)

p

0.1-1 (and every number and decimal in between)

n

1-13

m

1-13

R1, R2

Hydrogen or C1-C6 alkyl (linear or branched)

R3, R4

hydrogen or C1-C6-alkyl (linear or branched) or phenyl.

If the alcohol R in formula (I) is an alkoxylated alcohol group, then the hydroxy group in the alcohol reaction is as follows: R'-{[O-(AO) _x -]-OH} _q Formula (II) and "AO" is the unit resulting from the alkylene oxide monomer used to alkoxylate the alcohol, and "x" is the number of repeating units (in statistical average) with x = 1 to 200, preferably up to 100, more preferably up to 50, even more preferably up to 20, such as up to 40, 30, 25, 15, 10, 5 and any number between 1 and 200, and "q" denotes the number of (functionalized) hydroxy groups on the alcohol, with n = 1 to 50, preferably up to 20, more preferably up to 10, such as 25, 15, 5, 4, 3 and 2, and any number between 5 and 50.

It is clear to a person skilled in the art that the definition of the esteramines according to formula (I) and (II) is the result of an optimized way of carrying out the respective reaction and process, whereby all functional groups (of the respective starting material or any intermediate) have undergone a complete reaction. However, it is also clear that a complete reaction (the degree of conversion of 100%) is an idealized assumption. In reality, the degree of conversion is usually below 100%. Unreacted hydroxy groups, etc. may be present. This fact is known to the person skilled in the art for such reactions, as is the construction according to the formulas. Regardless, the reaction to obtain the mentioned structure is disclosed in the description above. By following the general reaction conditions as well as the specific reaction conditions described herein including the example section, the real structure for each individual case/reaction condition is obvious to a person skilled in the art or can be determined using standard procedures such as those described in the experimental section.

For the sake of completeness, in connection with the present invention, but in particular in connection with the esteramines according to formula (I) and even more the alkoxylation reactions which lead to the alcohols of formula (II), it is mentioned that the reactions used in the process according to the invention may be known to a person skilled in the art and may lead to statistical distributions. That is, if, for example, "20 ethylene oxide ("20 EO") units are used per functional group of the molecule to be reacted (i.e., hereinafter referred to as "core"), this does not necessarily mean that each of these functional groups of the core actually carries exactly 20 EO units; on the contrary, the resulting product obtained from such a reaction is a mixture of various slightly different products, the main product contained in the product of the process being the product with a core modified at each functional group with exactly 20 EO units per functional group; however, for statistical reasons, this "main product" (which is the target product of the reaction process and which is defined by the structure of formulas (I) and (II) considered here) is accompanied by many products which have slight variations from this main product, e.g. the same core molecule being modified with EO, but the lengths of the EO chains per functional group slightly deviating from 20: some chains are slightly longer and some are slightly shorter, a typically an even smaller amount carries even more EO and some even less EO, an even smaller amount differs to a greater extent, etc.
The more functional groups the core carries (e.g. the more hydroxy groups the alcohol carries) and the more e.g. alkylene oxide units are used per functional group, the greater the overall deviation from the “target molecule” represented via the formulas: This means that the content of the target molecule (represented in formula (I) and (II)) within the obtained product mixture decreases (i.e. this content is then below 100% of the total amount of B. obtained compound), and more different, minor variations of the target molecule are present in addition to the target molecule.
However, this does not pose a problem, since the explanation for such reactions here is the same "problem" observed for any single polymerization reaction: every polymer that is produced is defined by a chemical structure. However, the representation of such a polymer structure is just as difficult as for the structures considered in this present invention: the more precisely the structure of a polymer is defined, the more this represented structure is incorrect. Therefore, polymers are described by the monomers from which they are made, the reaction applied (e.g. “by radical polymerization”, which then implies how the monomeric units are linked) and certain other typical values such as the molecular weight Mw, Mn, the polydispersity index (i.e. the width of the molecular weight distribution), etc. - which is in fact nothing more than saying that the polymer product obtained from the polymer reaction is a mixture of different polymer molecules having different chain lengths, slightly different orders of monomeric units within a chain (if more than one monomer is used), slightly different amounts of each monomeric unit within a chain (if more than one monomeric unit is used), etc.
For the present structure considered in this present invention, the same difficulty may arise as explained for a description of a polymer molecule, but complicated by the fact that a defined organic molecule or molecules is also used: the molecule is/are a clearly chemically defined "organic structure" that can be precisely delimited. However, the modifications by the reaction according to the invention are introduced by addition reactions with usually incomplete conversion, thus introducing the same concept as in the description of polymers (and their "relative description" via starting materials, i.e. monomers) into an - according to formula - apparently clearly defined organic molecule.
This means for the structure currently considered that although it appears to be a clearly defined structure of a “typical organic molecule”, in reality this is not necessarily the case: the structure at hand is a combination of clearly defined organic chemical structure (i.e. the core, such as the individual starting materials A, B, C and D used) fused together, with “polymer descriptions” of the alkoxylated parts (if an alkoxylated alcohol is used; such parts that are oligomeric or polymeric depending on the amount of monomeric units used for the alkoxylation) and also depending on how complete the various esterifications proceed. This is to be taken into account when defining the structure at hand: the “organic structural parts” (i.e. the starting materials A, B, C and D) can be defined organically in a simple and unambiguous way, while the “polymeric structural parts” (i.e. the alkoxylated parts and the structures formed by esterification) - on paper - also follow the “organic chemical structural description” but should also be viewed through the eyes of a polymer chemist.
With this in mind, it is clear that the "structure of formula (I)" and "... of formula (II)" is a combination of organic chemical description for the starting materials used and a polymer chemical description for the aloxylated parts and the chains resulting from esterification reactions and thus the "target molecule" of the reaction, but not a "100% structure" as with other organic molecules: The structure shown is the "main component" of the described process, the product contains smaller amounts of many slight variations of this main component side by side, as explained hereinbefore.

process

1. (A) mindestens einen Alkohol mit mindestens einer Hydroxygruppe, wobei gegebenenfalls mindestens eine Hydroxygruppe in einem Schritt vor Schritt a) mit mindestens einem Alkylenoxid, bevorzugt mindestens 1 und bis zu 200, bevorzugt 1 bis 100, besonders bevorzugt bis zu 50 Mol Alkylenoxid pro Hydroxygruppe alkoxyliert werden kann,
2. (B) mit mindestens einem Lacton und/oder mindestens einer Hydroxysäure, besonders bevorzugt nur Lacton oder nur Hydroxysäure, besonders bevorzugt nur mindestens auf Lacton, ganz besonders bevorzugt nur einem Lacton, und
3. (C) mit mindestens einem Lactam und/oder mindestens einer Aminosäure, besonders bevorzugt nur Lactam oder nur Aminosäure, besonders bevorzugt nur Lactam, ganz besonders bevorzugt nur einem Lactam,
4. (D) in Gegenwart einer anorganischen oder organischen Säure, wobei die organische oder anorganische Säure vorzugsweise einen pKa-Wert im Bereich von -3 und bis +5, besonders bevorzugt von -2,5 bis 1,5 aufweist, eine solche Säure besonders bevorzugt eine organische Säure oder Schwefelsäure, besonders bevorzugt eine organische Säure, noch stärker bevorzugt eine Sulfonsäure, ganz besonders bevorzugt Methansulfonsäure,

wobei das molare Verhältnis von Komponente C (Lactam) zu Komponente D (Säure) innerhalb eines Bereichs von 1:0,9 bis 1 : 1,5, bevorzugt etwa 1:0,95 bis 1 : 1,1 und besonders bevorzugt 1:1 bis 1:1,08 und ganz besonders bevorzugt etwa 1:1,02 wie genau 1:1,02 liegt, und wobei das molare Verhältnis von Komponente C (Lactam) zur Gesamtzahl der Hydroxygruppen in Komponente A (Alkohol) höchstens 1:1 beträgt, vorzugsweise Komponente C kleiner als gleich der Gesamtzahl der Hydroxygruppen in Komponente A (Alkohol), und wobei das molare Verhältnis von Komponente B (Lacton/Hydroxysäure) zur Gesamtzahl der Hydroxygruppen in Komponente A (Alkohol) von 1:0,1 bis 1:10 beträgt.Also encompassed by this invention is a process for preparing an esteramine and its salt, preferably an esteramine and its salt according to any of the preceding embodiments disclosed hereinbefore, comprising the steps of reacting

1. (A) at least one alcohol having at least one hydroxyl group, where optionally at least one hydroxyl group can be alkoxylated in a step prior to step a) with at least one alkylene oxide, preferably at least 1 and up to 200, preferably 1 to 100, particularly preferably up to 50 mol of alkylene oxide per hydroxyl group,
2. (B) with at least one lactone and/or at least one hydroxy acid, particularly preferably only lactone or only hydroxy acid, particularly preferably only at least one lactone, very particularly preferably only one lactone, and
3. (C) with at least one lactam and/or at least one amino acid, particularly preferably only lactam or only amino acid, particularly preferably only lactam, very particularly preferably only one lactam,
4. (D) in the presence of an inorganic or organic acid, wherein the organic or inorganic acid preferably has a pKa value in the range from -3 to +5, particularly preferably from -2.5 to 1.5, such an acid particularly preferably being an organic acid or sulphuric acid, particularly preferably an organic acid, even more preferably a sulphonic acid, very particularly preferably methanesulphonic acid,

wherein the molar ratio of component C (lactam) to component D (acid) is within a range of 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1 and particularly preferably 1:1 to 1:1.08 and most preferably about 1:1.02 such as exactly 1:1.02, and wherein the molar ratio of component C (lactam) to the total number of hydroxyl groups in component A (alcohol) is at most 1:1, preferably component C is less than equal to the total number of hydroxyl groups in component A (alcohol), and wherein the molar ratio of component B (lactone/hydroxy acid) to the total number of hydroxyl groups in component A (alcohol) is from 1:0.1 to 1:10.

A, B, C and D are those as defined hereinbefore; Each of A, B, C and D can be individually selected from any of the embodiments mentioned herein and their preferred versions thereof, in particular from those mentioned in the section describing the esteramines and their salts of the invention.

The reaction of the process takes place by adding a mixture of starting materials A, B and C and then adding the acid; the addition of the acid is preferably carried out over a certain period of time. The reaction can take place in the presence of a solvent or without a solvent.

The reaction of the lactam ring is preferably carried out by reacting the at least one lactam and/or the amino acid with the at least one lactone and/or the hydroxy acid and with the acid. This reaction is carried out in an aqueous solution. In one embodiment of the present application, this reaction with the acid takes place in an aqueous solution that contains only water.

The term "aqueous solution" means that the solvent contains more than 50% by weight of water based on the total amount of solvent. In another embodiment, the term means that the solvent contains more than 80% by weight of water based on the total amount of solvent. In another embodiment, the term means that the solvent contains more than 95% by weight of water based on the total amount of solvent. In another embodiment, the term means that the solvent contains more than 99% by weight of water based on the total amount of solvent. In yet another embodiment, the term means that the solvent contains only water.
In another, more preferred embodiment, the reaction takes place while minimizing the solvent(s) used, i.e., under "substantially anhydrous conditions," meaning that the amount of water within the reaction mixture is minimized by not actively introducing water; however, water may be introduced as water of hydration and/or as an impurity in a compound used.

In one embodiment of the present invention, no additional solvent other than water is initially present in the process - except for water that may be introduced as an impurity in any of the feedstocks A, B, C and/or D. Preferably, such an amount of water is minimized by not using a feedstock that contains water; if an acid is used as an aqueous solution, the concentration of that acid is as high as is commercially acceptable, i.e., the typically "concentrated" acids as are commercially available are used.

Even if a hydroxy acid is used, water is formed during condensation; therefore, using lactones instead of hydroxy acids reduces the amount of water produced during the reaction and hence such lactones are preferred over using hydroxy acids.
Similarly, the lactams can be used liquid (usually at temperatures above room temperature, i.e. above their melting points), but for commercial reasons it may be preferred to use solid starting material as aqueous solutions due to much easier handling and also lower energy costs since melting is avoided.
In all those cases where water is used as part of the starting material(s), this water - including the water formed during the condensation reactions - must be removed during and/or after the reaction. The removal of the water can be carried out by the usual means, such as distilling water at elevated temperature or using reduced pressure, if necessary also at higher temperatures than room temperature.

In one embodiment of the present invention, the lactam is selected from the group consisting of a lactam having five carbon atoms in the lactam ring and a lactam having six carbon atoms in the lactam ring, and the reaction with acid is carried out in an aqueous solution. In another embodiment of the present invention, the lactam has five carbon atoms in the lactam ring, and the reaction with acid is carried out in an aqueous solution.
In a preferred embodiment of the above embodiments, the acid is an alkyl or aryl sulfonic acid, preferably an alkyl sulfonic acid and most preferably methane sulfonic acid.

In one embodiment, the lactam/amino acid is either dissolved in water or dispersed in an aqueous phase. The typical concentration of lactam/amino acid in water is in the range of 50 wt.% to 99 wt.%, based on the total weight of lactam/amino acid and water. In one In one embodiment of the present invention, the concentration of lactam/amino acid in water is in the range of 55 to 90% by weight, based on the total weight of the lactam/amino acid and the water. In another embodiment, the concentration of lactam/amino acid in water is in the range of 65 to 80% by weight, based on the total weight of the lactam/amino acid and the water.

In one embodiment, sulfuric acid is used as concentrated sulfuric acid. In another embodiment, sulfuric acid is used as a 96 to 98 wt.% sulfuric acid solution in water. In a further embodiment, sulfuric acid is used as an 80 wt.% sulfuric acid solution in water.
In a preferred embodiment, methanesulfonic acid is used as concentrated methanesulfonic acid. In another preferred embodiment, methanesulfonic acid is used as about 70 wt.% methanesulfonic acid solution in water or as "pure" acid, e.g., typically near 100 wt.% purity (equal to "about 100 wt.%); however, any concentration in between may be used. In another preferred embodiment, methanesulfonic acid is used as about 70 wt.% methanesulfonic acid solution in water.

In one embodiment of the present invention, the total amount of acid is added to the mixture of A+B+C at the beginning of the reaction. In another embodiment, the acid is added dropwise to the mixture of A+B+C for a period of 0.1 to 10 hours, provided that the acid is always present during the reaction.

For the reaction, the molar ratio of component C (lactam) to component D (acid) is in a range from 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1 and particularly preferably 1:1 to 1:1.08 and very particularly preferably about 1:1.02, i.e. exactly 1:1.02, and the ratio of component C (lactam) to the total number of hydroxyl groups in component A (alcohol) is at most 1:1, preferably the amount of component C is less than equal to the total number of hydroxyl groups in component A (alcohol), and the molar ratio of component B (lactone/hydroxy acid) to the total number of hydroxyl groups in component A (alcohol) is 1:0.1 to 1:10.

The reaction of the mixture of A+B+C in the presence of acid D takes place at temperatures of 50 to 150°C. In one embodiment of the invention, the reaction is carried out at temperatures of 80 to 140°C. In another embodiment, the reaction is carried out at temperatures of 90 to 130°C. In one embodiment of the present invention, the temperature is kept constant for the duration of the reaction. In another embodiment, the temperature is varied within the temperature range during the duration of the reaction. The reaction of the mixture of A+B+C in the presence of acid D is carried out for a duration of 0.1 to 15 hours. In another embodiment of the present invention, the duration is 1 to 10 hours. In another embodiment, the duration is 2 to 5 hours. In one embodiment of the present invention, the reaction is carried out under atmospheric pressure. In another embodiment, the reaction is carried out in a closed vessel under a pressure of 1 to 10 bar. In a further embodiment, the reaction is carried out in a closed vessel under a pressure of 1 to 5 bar. In another embodiment, the reaction is carried out in a closed vessel under a pressure of 1 to 4 bar.
In one embodiment, a protective atmosphere of, for example, nitrogen gas or argon gas is used to carry out the reaction. In another embodiment, the reaction is carried out at a temperature of 50 to 150°C at atmospheric pressure for a period of 0.1 to 10 hours. In a further embodiment of the present invention, the reaction is carried out at a temperature of 90 to 130°C for 3 hours under atmospheric pressure. In another embodiment of the present invention, the reaction is carried out at a temperature of 50 to 150°C for a period of 0.1 to 10 hours in a closed vessel under a pressure of 1.0 to 10 bar.

Although the invention is not intended to be limited, it is assumed that in principle three to five parallel esterification reactions take place in this reaction, depending on the starting material used: One esterification reaction is the reaction of the hydroxy group of the alcohol with the lactone/hydroxy acid; the second is the reaction of the hydroxy group of the alcohol with the lactam; the third is the reaction of the hydroxy group of the hydroxy acid or the opened lactone with the lactam; the fourth is the reaction of the hydroxy group of the hydroxy acid or the opened lactone with the sulfuric acid; the fifth is the reaction of the hydroxy group of the alcohol with the sulfuric acid.

An ester of the carboxyl group is formed by ring opening of the lactam with acid and at least one alcohol selected from the group consisting of i) linear alkyl alcohol with at least one hyd roxy group, ii) branched alkyl alcohol having at least one hydroxy group, iii) linear alkyl ether alcohol having at least one hydroxy group, iv) branched alkyl ether alcohol having at least one hydroxy group, v) phenoxyalkanols containing at least one hydroxy group, and vi) all mixtures thereof containing more than one alcohol selected from any group from i) to v).
A further ester is formed from sulphuric acid and at least one alcohol selected from the group consisting of I i) linear alkyl alcohol having at least one hydroxy group, ii) branched alkyl alcohol having at least one hydroxy group, iii) linear alkyl ether alcohol having at least one hydroxy group, iv) branched alkyl ether alcohol having at least one hydroxy group, v) phenoxyalkanols having at least one hydroxy group, and vi) all mixtures thereof containing more than one alcohol selected from any group from i) to v); This second esterification reaction does not take place with the other acids, i.e. not with acids such as methanesulphonic acid.

In one embodiment of the present invention, at least one linear or branched C2 to C36 alcohol is used which contains at least one hydroxy group. In a preferred embodiment thereof, at least one C8 to C22 fatty alcohol is used which contains at least one hydroxy group. In a more preferred embodiment thereof, a mixture of C16 and C18 fatty alcohols is used, each containing at least one hydroxy group. In another, more preferred embodiment thereof, a mixture of C18 and C22 fatty alcohols is used, each containing at least one hydroxy group. In a further, more preferred embodiment thereof, at least one branched C9 to C17 alcohol is used. In a further preferred embodiment thereof, linear or branched C8 to C10 monoalcohols are used which contain at least one hydroxy group. In a further, even more preferred embodiment thereof, 2-propylheptanol or 2-ethylhexanol is used. In a further, even more preferred embodiment thereof, 2-ethylhexanol is used.

In another embodiment, alkyl ether alcohols are used. Alkyl ether alcohols are, for example, alkyl alcohols that are alkoxylated with ethylene oxide and/or propylene oxide and/or butylene oxide. In one embodiment of the present invention, at least one linear or branched C2 to C36 alcohol is used that contains at least one, preferably at least two hydroxy groups that are alkoxylated with ethylene oxide and/or propylene oxide and/or butylene oxide. In another embodiment, at least one C8 to C22 alcohol is used that contains at least one, preferably at least two hydroxy groups that are alkoxylated with ethylene oxide and/or propylene oxide and/or butylene oxide.
Alkoxylation of the alcohol occurs either with only one alkylene oxide or with more than one alkylene oxide. When more than one alkylene oxide is used, the resulting alkyl ether alcohols comprise either randomly distributed alkylene oxide units or a block of one alkylene oxide followed by a block of another alkylene oxide. In one embodiment of the present invention, alkyl alcohols alkoxylated with only a single alkylene oxide are used. In another embodiment, alkyl alcohols alkoxylated with a first alkylene oxide are used, followed by alkoxylation with a second alkylene oxide, thereby forming a block structure of various alkylene oxide blocks. In yet another embodiment, alkoxylated 2-propylheptanol is used.

In another preferred embodiment of the present invention, at least one phenoxyalkanol is used. In another, more preferred embodiment, phenoxyethanol is used.

The esterification reaction of is carried out at temperatures in the range of 80 to 200 ° C. In another embodiment of the present invention, the esterification reaction is carried out at temperatures in the range of 120 to 140 ° C. In one embodiment of the present invention, the temperature is kept constant for the duration of the reaction. In another embodiment, the temperature is varied within the temperature range during the duration of the reaction. The reaction duration is 1 to 30 hours. In another embodiment of the present invention, the duration of the reaction is 2 to 5 hours. In another embodiment, the reaction is carried out in a closed vessel under a pressure of 1 to 10 bar. In another embodiment, the reaction is carried out in a closed vessel under a pressure of 1 to 5 bar. In another embodiment, the reaction is carried out in a closed vessel under a pressure of 1 to 4 bar. In one embodiment, a protective atmosphere of, for example, nitrogen gas or argon gas is used to carry out the reaction. In another embodiment, the reaction is carried out at a temperature of 80 to 200°C at atmospheric pressure for a period of 0.1 to 10 hours. In a further embodiment of the present invention, the reaction is carried out at a temperature of 90 to 130°C for 3 hours under atmospheric pressure. In another embodiment of the present invention, the reaction is carried out at a temperature of 80 to 200°C for a period of 0.1 to 30 hours in a closed vessel under a pressure of 1.0 to 10 bar.

In one embodiment of the present invention, the reaction is carried out by reacting at least one lactam having at least 3 carbon atoms in an aqueous solution and at least one alcohol selected from the group consisting of linear alkyl alcohol containing at least one hydroxy group, branched alkyl alcohol containing at least one hydroxy group, linear alkyl ether alcohol containing at least one hydroxy group, branched alkyl ether alcohol containing at least one hydroxy group, phenoxyalkanols containing at least one hydroxy group, and all mixtures thereof, and at least one lactone and/or hydroxy acid as previously defined, and adding acid, followed by sealing the vessel to react the mixture at a temperature of 80 to 200°C for 1 to 30 h.
In a further embodiment of the present invention, the reaction is carried out by mixing at least one lactam having at least 3 carbon atoms and at least one alcohol selected from the group consisting of linear alkyl alcohol containing at least one hydroxy group, branched alkyl alcohol containing at least one hydroxy group, linear alkyl alcohol containing at least one hydroxy group, branched alkyl ether alcohol containing at least one hydroxy group, phenoxyalkanols containing at least one hydroxy group, and all mixtures thereof, and at least one lactone and/or hydroxy acid as previously defined, and adding acid, followed by sealing the vessel to react the mixture at a temperature of 80 to 200°C for 1 to 30 h at a pressure of 1.0 to 10 bar.

After the reaction, water and/or excess alcohol can be removed. The removal of water and alcohol can be carried out by any technique known in the art, for example by applying a vacuum. In one embodiment of the present invention, the optional removal of water and/or excess alcohol is carried out by applying a vacuum in the range from 0.1 mbar to 800 mbar. In another embodiment, a vacuum in the range from 1 mbar to 500 mbar is applied. In a further embodiment, a vacuum in the range from 10 mbar to 100 mbar is applied.

Uses

Another object of the present invention is the use of the above-mentioned esteramines and their salts in cleaning agents.
The esteramines and their salts can be added to cleaning agents.

The esteramines and/or their salts are present in the formulations mentioned in a concentration of 0.1 to 5 wt.%, preferably in a concentration of 0.5 to 2 wt.%.

The esteramines and their salts of the present invention can also be added to a cleaning composition comprising from about 1% to about 70% by weight of a surfactant system. The esteramines and/or their salts of the present invention can be present in a cleaning composition at a concentration of from about 0.1% to about 5% by weight of the composition, or at a concentration of from about 0.5% to about 2% by weight of the composition.

Therefore, a further object of the present invention is the use of the esteramines and their salts of this invention and/or obtained by a process according to the invention and/or as described above, in textile and household care products, in particular cleaning agents for improved removal of oily and greasy stains, removal of solid dirt such as clay, prevention of greying of fabric surfaces and/or anti-limescale agents, wherein the cleaning composition is preferably a detergent formulation and/or a dishwashing detergent formulation, particularly preferably a liquid detergent formulation and/or a liquid hand dishwashing detergent formulation.

A further subject matter of the present invention is therefore also a cleaning composition, a textile and household care product, an industrial and institutional cleaning product, preferably in detergents, in cleaning agents and/or in textile and household care products, each containing at least one esteramine or salt thereof as defined above or which can be obtained or obtained by a process according to the invention and/or as described herein.
Another object of the present invention is a textile and household care product, a cleaning composition, an industrial and institutional cleaning product, preferably a washing agent, a cleaning composition and/or a fabric and household care product, each containing at least one esteramine or salt thereof.

In a preferred embodiment, it is a cleaning composition and/or a fabric and household care product and/or an industrial and institutional cleaning product containing at least one esteramine or salt thereof as defined above. In particular, it is a cleaning composition for improving cleaning performance, in particular an improved primary rinse, preferably a detergent formulation and/or a manual dishwashing detergent formulation, particularly preferably a liquid detergent formulation and/or a liquid manual dishwashing detergent formulation.

In a preferred embodiment, the cleaning composition according to the invention is a liquid or solid detergent composition, preferably a liquid detergent composition.

In another preferred embodiment, the cleaning composition according to the invention is a liquid or solid (e.g. powder or tablet/unit dose) detergent composition for manual or machine dishwashing, preferably a liquid manual dishwashing detergent composition. Such compositions are known to a person skilled in the art.

In another embodiment, the cleaning composition of the present invention is a hard surface cleaning composition that can be used to clean various surfaces such as hardwood, tile, ceramic, plastic, leather, metal, glass.

In one embodiment of the present invention, the esteramine according to the invention or its salt is a component of a cleaning agent or a textile and household care agent, preferably a laundry cleaning composition, a laundry care agent or laundry treatment product or laundry detergent, preferably a liquid detergent formulation or a liquid detergent product, each of which additionally contains at least one surfactant, preferably at least one anionic surfactant.

In one embodiment, it is also preferred within the scope of the present invention that the cleaning composition (in addition to at least one esteramine or salt thereof, as described above) additionally comprises at least one enzyme, preferably selected from one or more optionally further comprising at least one enzyme, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, hemicellulases, phospholipases, esterases, pectinases, lactases, pectate lyases, cutinases, DNases, xylanases, oxyreductases, dispersins, mannanases and peroxidases as well as combinations of at least two of the aforementioned types, preferably wherein at least one enzyme is selected from lipases.
Even more preferred are the cleaning compositions of the present invention which contain at least one esteramine or salt according to the invention and optionally further comprise at least one surfactant or surfactant system - as previously described - those for improved cleaning performance in laundry and manual dishwashing applications, more particularly for improved cleaning performance (such actions as previously described), such as. B. those on textiles and dishes, and can additionally contain at least one enzyme selected from the list consisting of optionally further comprising at least one enzyme, preferably selected from one or more optionally further comprising at least one enzyme, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, hemicellulases, phospholipases, esterases, pectinases, lactases, pectate lyases, cutinases, DNases, xylanases, oxicoreductases, dispersins, mannanases and peroxidases and combinations of at least two of the preceding types, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases and combinations of at least two of the preceding types, particularly preferably at least one enzyme is selected from lipases.

In one embodiment, the esteramine or salt thereof according to the invention can be used in cleaning compositions comprising a surfactant system comprising C10-C15 alkylbenzenesulfonates (LAS) as the primary surfactant and one or more additional surfactants selected from nonionic, cationic, amphoteric, zwitterionic or other anionic surfactants or mixtures thereof.

In a further embodiment, the esteramine according to the invention or its salt can be used in cleaning agents or textile and household care products, preferably in a laundry cleaning composition, a laundry care agent or laundry detergent, preferably a liquid detergent formulation or a liquid detergent product, containing C12-C18 alkyl ethoxylate surfactants having 5-10 ethoxy units as primary surfactant and one or more additional surfactants selected from anionic, cationic, amphoteric, zwitterionic or other nonionic surfactants or mixtures thereof.

In a further embodiment, the esteramine or its salt according to the invention can be used in the cleaning agents or fabric and household care agents, preferably in a laundry cleaning composition, a laundry care agent or laundry treatment agent or laundry detergent, preferably a liquid detergent formulation or a liquid detergent product comprising C8-C18 linear or branched alkyl ether sulfates having 1-5 ethoxy units as primary surfactant and one or more additional surfactants selected from nonionic, cationic, amphoteric, zwitterionic or other anionic surfactants or mixtures thereof.
In one embodiment of the present invention, the esteramine or salt thereof is a component of a cleaning composition, such as preferably a laundry or dishwashing formulation, more preferably a liquid laundry or manual dishwashing formulation, each additionally containing at least one surfactant, preferably at least one anionic surfactant.

In a further embodiment, this invention also encompasses a composition comprising at least one esteramine or salt thereof as hereinbefore described, further comprising an antimicrobial agent as disclosed hereinafter, preferably selected from the group consisting of 2-phenoxyethanol, more preferably comprising the antimicrobial agent in an amount ranging from 2 ppm to 5% by weight of the composition; even more preferably containing 0.1 to 2% phenoxyethanol.
In a further embodiment, this invention also comprises a composition, preferably a cleaning composition, more preferably a liquid detergent composition or a liquid hand dishwashing composition, even more preferably a liquid detergent composition or a liquid fabric softener composition for use in the laundry, such a composition comprising an esteramine or its salt in the amounts described above, as described hereinbefore. Such a composition further comprises 4,4'-dichoro-2-hydroxydiphenyl ether in a concentration of 0.001 to 3%, preferably 0.002 to 1%, more preferably 0.01 to 0.6% by weight of the composition in each case.

In a further embodiment, this invention also encompasses a composition, in particular a cleaning composition, more preferably a cleaning composition in liquid, solid or semi-solid form, preferably a concentrated liquid detergent formulation, a single dose detergent formulation, a liquid hand dishwashing formulation or a solid automatic dishwashing formulation, more preferably a detergent formulation containing an esteramine or its salt as described herein and in the amounts as described above, such composition preferably being a detergent composition, such composition further comprising an antimicrobial agent as disclosed below, preferably selected from the group consisting of 2-phenoxyethanol, more preferably the antimicrobial agent in an amount ranging from 2 ppm to 5% by weight of the composition; even more preferably containing 0.1 to 2% phenoxyethanol.

In a further embodiment, this invention also encompasses a method of preserving an aqueous composition against microbial contamination or growth, in particular a cleaning composition, more preferably a cleaning composition in liquid, solid or semi-solid form, preferably a concentrated liquid detergent formulation, a single dose detergent formulation, a liquid hand dishwashing formulation or a solid machine dishwashing formulation. More preferably, a detergent formulation comprising an esteramine or its salt as described herein and in the amounts described above, such composition preferably being a detergent composition, such method comprising the addition of at least one antimicrobial agent selected from the disclosed antimicrobial agents as disclosed below, said antimicrobial agent preferably being 2-phenoxyethanol.

In a further embodiment, this invention also encompasses a method for washing fabrics or cleaning hard surfaces, which method comprises treating a fabric or hard surface with a cleaning composition, more preferably a liquid detergent composition or a liquid hand dishwashing composition, even more preferably preferably a liquid detergent composition or a liquid fabric softener composition for laundry use, such a composition comprising an esteramine or its salt in the amounts described above, such composition further comprising 4,4'-dichoro-2-hydroxydiphenyl ether.
As used herein, the term "cleaning agent" as used for the compositions and products of the present invention encompasses compositions and formulations designed to clean soiled material. Such compositions include, but are not limited to, laundry detergent and laundry detergents, fabric softening agents, fabric improvement compositions, fabric fresheners, laundry prewash, laundry pretreatment, laundry additives, spray products, chemical cleaning agents or compositions, laundry rinse additive, laundry additive, post-rinse fabric treatment, ironing aids, dishwashing detergents, hard surface cleaners, unit dose formulations, delayed delivery formulation, detergent contained on or in a porous substrate or nonwoven film, and other suitable forms that may be apparent to one of skill in the art in view of the teachings contained herein. Such compositions may be used as a prewash treatment, a postwash treatment, or may be added during the rinse or wash cycle of the laundry process. The cleaning compositions may be in a form selected from liquid, powder, single-phase or multi-phase unit dose, sachet, tablet, gel, paste, bar or flake.

The cleaning compositions of the present invention comprise a surfactant system in an amount sufficient to provide the desired cleaning properties. In some embodiments, the cleaning composition comprises from about 1% to about 70% of a surfactant system by weight of the composition. In other embodiments, the liquid cleaning composition comprises from about 2% to about 60% of the surfactant system by weight of the composition. In further embodiments, the cleaning composition comprises from about 5% to about 30% of the surfactant system by weight of the composition. The surfactant system can comprise a surfactant selected from anionic surfactants, nonionic surfactants, cationic surfactants, zwitterionic surfactants, amphoteric surfactants, ampholytic surfactants, and mixtures thereof. One of ordinary skill in the art will understand that a deterrent surfactant comprises any surfactant or mixture of surfactants capable of cleaning, removing stains, or laundering soiled material.

More preferably, the compositions or products of the present invention as described herein contain at least one esteramine and/or its salt according to the invention obtained or obtainable by the process according to the invention as described herein and, in the amounts as indicated in the previous paragraph, optionally further comprise at least one surfactant or surfactant system in amounts of from about 1% to about 70% by weight of the composition or product, are preferably those for primary cleaning (i.e., stain removal) and particularly preferably within laundry applications, and may additionally comprise at least one enzyme selected from lipases, hydrolases, amylases, proteases, cellulases, mannanases, hemicellulases, phospholipases, esterases, xylanases, DNases, dispersins, pectinases, oxidoreductases, cutinases, lactases and peroxidases, particularly preferably at least two of the aforementioned types.

The term "cleaning agents" as used herein includes compositions and formulations as well as products designed to clean soiled material. Such compositions, formulations and products include those designed to clean soiled material or soiled surfaces of any kind.

Compositions for “industrial and institutional cleaning” include those cleaning compositions designed for use in industrial and institutional cleaning, such as those for cleaning soiled material or surfaces of any kind, such as hard surface cleaners for surfaces of any kind including tiles, carpets, PVC surfaces, wooden surfaces, metal surfaces, painted surfaces.

“Textile and home care compositions” include cleaning agents including, but not limited to, laundry detergents and laundry detergents, fabric softening compositions, fabric improvement compositions, fabric refreshers, laundry pre-wash, laundry pre-treatment, laundry additives, spray products, chemical cleaning agents or compositions, laundry rinse additive, laundry additive, post-rinse fabric treatment, ironing aid, dishwashing detergent, hard surface cleaner, unit dose formulation, sustained release formulation, cleaning agents contained on or in a porous substrate or nonwoven film, and others suitable forms which may be apparent to one skilled in the art in view of the teachings contained herein. Such compositions may be used as a pre-wash treatment, as a post-wash treatment, or may be added during the rinse or wash cycle of the laundry operation, preferably during the wash cycle of the laundry or dishwashing operation.

The cleaning compositions of the invention may be in any form, namely a liquid; a solid such as a powder, a granule, an agglomerate, a paste, a tablet, a sachet, a bar, a gel; an emulsion; types supplied in two or more compartment containers; single-phase or multi-phase single dose; a spray or foam detergent; pre-moistened wipes (i.e. the cleaning composition in combination with a nonwoven material as described in US$6,121,165 , Mackey, et al.); Dry wipes (ie the cleaning composition in combination with a nonwoven fabric as discussed in US$5,980,931 , Fowler, et al.) are activated by a user or consumer with water; and other homogeneous, inhomogeneous, or single-phase or multiphase detergent forms.
The liquid cleaning agents of the present invention preferably have a viscosity of from 50 to 10,000 mPa*s; liquid manual dishwashing agents (also liquid manual "dishwashing detergent agents") have a viscosity of preferably from 100 to 10,000 mPa*s, more preferably from 200 to 5,000 mPa*s and most preferably from 500 to 3,000 mPa*s at 20 1/s and 20°C; liquid laundry cleaning agents have a viscosity of preferably from 50 to 3,000 mPa*s, more preferably from 100 to 1,500 mPa*s and most preferably from 200 to 1,000 mPa*s at 20 1/s and 20°C.

The cleaning compositions may also contain supplemental cleaning additives. Suitable supplemental cleaning additives include builders, structurants or thickeners, clay soil removal/anti-redeposition agents, polymeric soil release agents, polymeric dispersants, polymeric grease cleaners, enzymes, enzyme stabilizing systems, bleaching compounds, bleaching agents, bleach activators, bleach catalysts, brighteners, dyes, colorants, color transfer inhibitors, chelating agents, suds suppressors, softeners and fragrances.

All such cleaning agents, their components including (additional) cleaning additives, their general compositions and more specific compositions are known, for example as described in publications 800542 and 800500 as published by Protegas, Liechtenstein, and also from WO 2022/136409 and the WO 2022/136408 wherein in each of the prior art the esteramines and their salts within the general compositions and also any individualized specific cleaning composition disclosed in the aforementioned publications may be partially or completely replaced by the esteramines and/or their salts of this present invention. In the aforementioned documents various types of formulations for cleaning agents are also disclosed; all such types of compositions - the general compositions and also any individualized specific cleaning composition - may equally be applied to the cleaning compositions contemplated herein.
Thus, the present invention also encompasses all such disclosed compositions of the above-mentioned disclosures from the prior art, but in addition at least one of the esteramines according to the invention and/or their salts in addition to or as a replacement for an esteramine or esteramine salt already contained in such prior art or such a compound that can be replaced by such esteramine or salts according to the invention - such replacements that are known to a person skilled in the art -. wherein the content of the esteramine according to the invention or its salt in the formulations mentioned is present in a concentration of generally 0.05 to 20 wt. %, preferably up to 10 wt. %, particularly preferably 0.1 to 5 wt. %, even more preferably in a concentration of 0.5 to 2 wt. %.

The liquid cleaning compositions of the present invention may have any suitable pH. Preferably, the pH of the composition is adjusted to a value between 4 and 14. More preferably, the composition has a pH of from 6 to 13, even more preferably from 6 to 10, most preferably from 7 to 9. The pH of the composition may be adjusted using pH modifying ingredients known in the art and is measured as a 10% product concentration in demineralized water at 25°C. For example, NaOH may be used and the actual weight percent of NaOH may be varied and trimmed to the desired pH, such as pH 8.0. In one embodiment of the present invention, a pH >7 is adjusted using amines, preferably alkanolamines, most preferably triethanolamine.

The selection of additional surfactants and other ingredients (both described in more detail below in the “Cleaning Additives” chapter) in these embodiments may depend on the application and the desired benefit.

General description of cleaning agents, formulations and their ingredients

Cleaning compositions such as fabric and household care products and formulations for industrial and institutional cleaning, in particular such as laundry and hand dishwashing detergents, are known to those skilled in the art. Any composition etc. known to a person skilled in the art can be used in connection with the respective use by containing at least one compound according to the invention, preferably at least one such compound according to the invention in amounts suitable for expressing a particular property within such a composition, in particular when such a composition is used in its field of use.

Cleaning additives

The cleaning agents and formulations according to the invention can - and preferably do - contain additional cleaning additives (also abbreviated herein as "auxiliaries"), such additives preferably being in addition to a surfactant system as previously defined. Suitable supplementary cleaning additives include builders, co-builders, structurants or thickeners, clay soil removal/anti-redeposition agents, polymeric soil release agents, dispersants such as polymeric dispersants, polymeric grease cleaners, solubilizers, chelating agents, enzymes, enzyme stabilizing systems, bleaches, bleaching agents, bleach activators, bleach catalysts, brighteners, anti-odor agents, pigments, dyes, opacifiers, dyes, color transfer agents, chelating agents, foam enhancers, foam suppressors (antifoam agents), color speckles, silver care, anti-tarnish and/or corrosion inhibitors, alkalinity sources, pH adjusters, pH buffering agents, hydrotropes, detergent particles, antibacterial agents, antioxidants, plasticizers, carriers, processing aids, pro-fragrances and perfumes. All of these supplements are explained in detail and by way of example further below in the following chapters. Liquid cleansers may additionally include rheology control/modifiers, emollients, humectants, skin rejuvenating agents and solvents - and preferably include at least one of these.
Solid compositions may additionally comprise fillers, bleaching agents, bleach activators and catalytic materials - and preferably also comprise at least one of these. Suitable examples of such cleaning additives and uses can be found in WO 99/05242 , US Patent No. 5,576,282 , 6,306,812 B1 and 6,326,348 B1 .

One of ordinary skill in the art will understand that a deterrent surfactant includes any surfactant or mixture of surfactants that can clean, remove stains or wash soiled material.
Therefore, the cleaning agents according to the invention, such as fabric and household care products, as well as formulations for industrial and institutional cleaning, in particular such as laundry detergents and hand dishwashing detergents, preferably additionally comprise a surfactant system and even more preferably also further additives, such as those described in more detail above and below.
The surfactant system may be comprised of one surfactant or a combination of surfactants selected from anionic surfactants, nonionic surfactants, cationic surfactants, zwitterionic surfactants, amphoteric surfactants, and mixtures thereof. One of ordinary skill in the art will understand that a surfactant system for detergents includes any surfactant or mixture of surfactants that provides cleaning, stain removal, or laundering benefits to soiled material.
The cleaning compositions of the present invention preferably comprise a surfactant system in an amount sufficient to provide the desired cleaning properties. In some embodiments, the cleaning composition comprises from about 1% to about 70% of a surfactant system by weight of the composition. In other embodiments, the liquid cleaning composition comprises from about 2% to about 60% of the surfactant system by weight of the composition. In further embodiments, the cleaning composition comprises from about 5% to about 30% of the surfactant system by weight of the composition. The surfactant system may comprise a surfactant selected from anionic surfactants, nonionic surfactants, cationic surfactants, zwitterionic surfactants, amphoteric surfactants, and mixtures thereof.

Fabric detergent compositions

‘Fabric detergent composition’ may be any composition, formulation or product intended for use in laundry, including laundry care, laundry cleaning, etc.; therefore, this term is used hereinafter to refer to any composition, formulation or product.

In detergent compositions, anionic surfactants generally make up by far the largest proportion of surfactants within such a formulation. Therefore, the cleaning agents according to the invention for use in laundry preferably comprise at least one anionic surfactant and optionally further surfactants selected from one of the surfactant classes described herein, preferably from nonionic surfactants and/or amphoteric surfactants and/or zwitterionic surfactants and/or cationic surfactants.

Cleaning agents can - and preferably do - contain anionic surfactants, which can also be used in combinations with more than one other surfactant.
Non-limiting examples of anionic surfactants - which may also be used in combinations of more than one surfactant - useful herein include C9-C20 linear alkylbenzenesulfonates (LAS), C10-C20 primary, branched chain and random alkyl sulfates (AS); C10-C18 secondary (2,3) alkyl sulfates; C10-C18 alkyl alkoxy sulfates (AExS) where x is from 1 to 30; C10-C18 alkyl alkoxy carboxylates comprising 1 to 5 ethoxy units; medium chain branched alkyl sulfates as in US$6,020,303 and US$6,060,443 discussed; medium-chain branched alkyl alkoxy sulfates, as in US$6,008,181 and US$6,020,303 discussed; modified alkylbenzenesulfonate (MLAS), as in WO 99/05243 , WO 99/05242 and WO 99/05244 discussed; methyl ester sulfonate (MES); and alpha-olefin sulfonate (AOS).
Preferred examples of suitable anionic surfactants are alkali metal and ammonium salts of C8-C12 alkyl sulfates, of C12-C18 fatty alcohol ether sulfates, of C12-C18 fatty alcohol polyether sulfates, of sulfuric acid half esters of ethoxylated C4-C12 alkylphenols (ethoxylation: 3 to 50 mol ethylene oxide/mol), of C12-C18 alkylsulfonic acids, of C12-C18 sulfo fatty acid alkyl acids, e.g. of C12-C18 sulfo fatty acid methyl esters, of C10-C18 alkylarylsulfonic acids, preferably of n-C10-C18 alkylbenzenesulfonic acids, of C10-C18 alkylalkoxycarboxylcarboxylates and of soaps such as C8-C24 carboxylic acids. The alkali metal salts of the aforementioned compounds are preferred, particularly preferably the sodium salts. In one embodiment of the present invention, anionic surfactants are selected from n-C10-C18-alkylbenzenesulfonic acids and from fatty alcohol polyether sulfates, which in the context of the present invention are in particular sulfuric acid half esters of ethoxylated C12-C18-alkanols (ethoxylation: 1 to 50 mol ethylene oxide/mol), preferably n-C12-C18-alkanols.
In one embodiment of the present invention, alcohol polyether sulfates derived from branched (ie synthetic) C11-C18 alkanols (ethoxylation: 1 to 50 mol ethylene oxide/mol) can also be used.
Preferably, the alkoxylation group of both types of alkoxylated alkyl sulfates based on C12-C18 fatty alcohols or based on branched (i.e. synthetic) C11-C18 alcohols is an ethoxylation group, and an average degree of ethoxylation of one of the alkoxylated alkyl sulfates is 1 to 5, preferably 1 to 3.
Preferably, the detergent formulation according to the invention comprises at least 1 wt.% to 50 wt.%, preferably in the range of greater than or equal to about 2 wt.% to equal to or less than about 30 wt.%, more preferably in the range of greater than or equal to 3 wt.% to less than or equal to 25 wt.%, and most preferably in the range of greater than or equal to 5 wt.% to less than or equal to 25 wt.% of one or more anionic surfactants as described above, based on the respective total composition, including other components and water and/or solvents.
In a preferred embodiment of the present invention, anionic surfactants are selected from C10-C15 linear alkylbenzenesulfonates, C10-C18 alkyl ether sulfates having 1-5 ethoxy units and C10-C18 alkyl sulfates.

in dem die Variablen wie folgt definiert sind:

R1

ausgewählt ist aus linearem C1-C10-Alkyl, bevorzugt Ethyl und besonders bevorzugt Methyl,

R2

ausgewählt ist aus C8-C22-Alkyl, z.B. n-C8H17, n-C10H21, n-C12H25, n-C14H29, n-C16H33 oder n-C18H37,

R3

ausgewählt ist aus C1-C10-Alkyl, Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, Isobutyl, sec-Butyl, tert-Butyl, n-Pentyl, Isopentyl, sec-Pentyl, Neopentyl, 1,2-Dimethylpropyl, Isoamyl, n-Hexyl, Isohexyl, sec-Hexyl, n-Heptyl, n-Octyl, 2-Ethylhexyl, n-Nonyl, n-Decyl oder Isodecyl,

m und n

liegen im Bereich von null bis 300, wobei die Summe von n und m mindestens eins ist. Vorzugsweise liegt m im Bereich von 1 bis 100 und n im Bereich von 0 bis 30.

Cleaning agents can also contain non-ionic surfactants - which can also be used in combinations of more than one other surfactant.
Non-limiting examples of nonionic surfactants - which can also be used in combinations of more than one other surfactant - include: C8-C18 alkyl ethoxylates such as nonionic NEODOL surfactants® from Shell; ethylene oxide/propylene oxide block alkoxylates as PLURONIC® from BASF; C14-C22 medium chain branched alkyl alkoxylates, BAEx, where x is from 1 to 30, as in US$6,153,577 , US$6,020,303 and US$6,093,856 discussed; alkyl polysaccharides, as in US$4,565,647 Llenado, published on 26 January 1986; in particular alkyl polyglycosides, as in US$4,483,780 and US$4,483,779 discussed; Polyhydroxy fatty acid amides, as in US$5,332,528 discussed; and ether-capped poly(oxyalkylated) alcohol surfactants, as in US$6,482,994 and WO 01/42408 discussed.
Preferred examples of non-ionic surfactants are in particular alkoxylated alcohols and alkoxylated fatty alcohols, di- and multiblock copolymers of ethylene oxide and propylene oxide and reaction products of sorbitan with ethylene oxide or propylene oxide, as well as alkylphenol ethoxylates, alkyl glycosides, polyhydroxy fatty acid amides (glucamides). Examples of (additional) amphoteric surfactants are so-called amine oxides.
Preferred examples of alkoxylated alcohols and alkoxylated fatty alcohols are, for example, compounds of the general formula (A)

in which the variables are defined as follows:

R1

is selected from linear C1-C10 alkyl, preferably ethyl and particularly preferably methyl,

R2

is selected from C8-C22 alkyl, e.g. n-C8H17, n-C10H21, n-C12H25, n-C14H29, n-C16H33 or n-C18H37,

R3

is selected from C1-C10 alkyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, 1,2-dimethylpropyl, isoamyl, n-hexyl, isohexyl, sec-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl or isodecyl,

m and n

are in the range from zero to 300, where the sum of n and m is at least one. Preferably, m is in the range from 1 to 100 and n is in the range from 0 to 30.

in dem die Variablen wie folgt definiert sind:

R1

gleich oder verschieden ist und ausgewählt ist aus linearem C1-C4-Alkyl, bevorzugt jeweils identisch und Ethyl und besonders bevorzugt Methyl,

R4

ausgewählt ist aus C6-C20-Alkyl, insbesondere n-C8H17, n-C10H21, n-C12H25, n-C14H29, n-C16H33, n-C18H37,

ein

eine Zahl im Bereich von Null bis 6, vorzugsweise 1 bis 6 ist,

b

eine Zahl im Bereich von Null bis 20, vorzugsweise 4 bis 20 ist,

d

ist eine Zahl im Bereich von 4 bis 25.

Compounds of the general formula (A) can be block copolymers or random copolymers, with block copolymers being preferred.
Further preferred examples of alkoxylated alcohols and alkoxylated fatty alcohols are, for example, compounds of the general formula (B)

in which the variables are defined as follows:

R1

is the same or different and is selected from linear C1-C4-alkyl, preferably identical in each case, and ethyl and particularly preferably methyl,

R4

is selected from C6-C20-alkyl, in particular n-C8H17, n-C10H21, n-C12H25, n-C14H29, n-C16H33, n-C18H37,

a

is a number in the range from zero to 6, preferably 1 to 6,

b

is a number in the range from zero to 20, preferably 4 to 20,

d

is a number in the range 4 to 25.

Preferably, at least one of a and b is greater than zero.
Compounds of the general formula (B) can be block copolymers or random copolymers, with block copolymers being preferred.
Other suitable nonionic surfactants are selected from di- and multiblock copolymers composed of ethylene oxide and propylene oxide. Other suitable nonionic surfactants are selected from ethoxylated or propoxylated sorbitan esters. Alkylphenol ethoxylates or alkyl polyglycosides or Polyhydroxy fatty acid amides (glucamides) are also suitable. An overview of other suitable non-ionic surfactants can be found in EP-A 0 851 023 and in DE-A 198 19 187 .
Of course, mixtures of two or more different non-ionic surfactants can also be present.
In a preferred embodiment of the present invention, nonionic surfactants are selected from C12/14 and C16/18 fatty alcohol alkoxylates, C13/15 oxo alcohol alkoxylates, C13 alcohol alkoxylates and 2-propylheptyl alcohol alkoxylates, each with 3-15 ethoxy units, preferably 5-10 ethoxy units, or with 1-3 propoxy and 2-15 ethoxy units.

Cleaning agents can also contain amphoteric surfactants - which can also be used in combinations of more than one other surfactant.
Non-limiting examples of amphoteric surfactants - which may also be used in combinations of more than one other surfactant - include: water-soluble amine oxides containing one alkyl moiety of about 8 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl moieties and hydroxyalkyl moieties containing about 1 to about 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of about 10 to about 18 carbon atoms and a moiety selected from the group consisting of alkyl moieties and hydroxyalkyl moieties of about 1 to about 3 carbon atoms. See WO 01/32816 , US$4,681,704 and US$4,133,779 . Suitable surfactants thus include so-called amine oxides, such as lauryldimethylamine oxide ("lauramine oxide"). Preferred examples of amphoteric surfactants are amine oxides. Preferred amine oxides are alkyldimethylamine oxides or alkylamidopropyldimethylamine oxides, particularly preferably alkyldimethylamine oxides and in particular cocodimethylamine oxides. Amine oxides can have a linear or medium-branched alkyl moiety. Typical linear amine oxides include water-soluble amine oxides which contain an R1 = C8-18 alkyl radical and two R2 and R3 units selected from the group consisting of C1-C3 alkyl groups and C1-C3 hydroxyalkyl groups. The amine oxide is preferably characterized by the formula R1-N(R2)(R3)-O wherein R1 is C8-18 alkyl and R2 and R3 are selected from the group consisting of methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl, 2-hydroxypropyl and 3-hydroxypropyl. The linear amine oxide surfactants may particularly include linear C10-C18 alkyldimethylamine oxides and linear C8-C12 alkoxyethyldihydroxyethylamine oxides. Preferred amine oxides include linear C10, linear C10-C12 and linear C12-C14 alkyldimethylamine oxides. As used herein, "medium branched" means that the amine oxide has an alkyl radical having n1 carbon atoms with an alkyl branch on the alkyl radical having n2 carbon atoms. The alkyl branch is located on the alpha carbon of the nitrogen on the alkyl portion. This type of branching for the amine oxide is also known in the art as an internal amine oxide. The total of n1 and n2 is 10 to 24 carbon atoms, preferably 12 to 20, and more preferably 10 to 16. The number of carbon atoms for the one alkyl group (n1) should be approximately the same number of carbon atoms as the one alkyl branch (n2) so that the one alkyl group and the one alkyl branch are symmetrical. As used herein, "symmetrical" means that (n1-n2) is less than or equal to 5, preferably 4, most preferably 0 to 4 carbon atoms in at least 50%, more preferably at least 75% to 100% by weight of the mid-branched amine oxides used herein. The amine oxide further comprises two units independently selected from a C1-C3 alkyl, a C1-C3 hydroxyalkyl group, or a polyethylene oxide group containing an average of about 1 to about 3 ethylene oxide groups. Preferably, the two units are selected from a C1-C3-alkyl, more preferably both are selected as C1-alkyl.
In a preferred embodiment of the present invention, amphoteric surfactants are selected from C8-C18 alkyldimethylamine oxides and C8-C18 alkyldi(hydroxyethyl)amine oxide.

Cleaning agents can also contain zwitterionic surfactants – which can also be used in combinations of more than one other surfactant.
Suitable zwitterionic surfactants include betaines, such as alkyl betaines, alkylamidobetaine, amidazolinium betaine, sulfobetaine (INCI sultaines) and phosphobetaines. Examples of suitable betaines and sulfobetaines are the following (designated according to INCI): Mandelamidopropyl of betaines, Apricotamidopropyl betaines, Avocadamidopropyl of betaines, Babassuamidopropyl of betaines, Behenamidopropyl betaines, Behenyl of betaines, Canol amidopropyl betaine, Capryl/Capramidopropyl betaines, Carnitine, Cetyl of betaines, Cocamidoethyl of betaines, Cocamidopropyl betaines, Cocamidopropyl hydroxysultaine, Coco betaines, Coco Hydroxysultaine, Coco/Oleam Idopropyl-Betaine, Coco-Sultaine, Decyl-Betaine, Dihydroxyethyl Oleyl Glycinate, Dihydroxyethyl Soya Glycinate, Dihydroxyethyl Stearyl Glycinate, Dihydroxyethyl Tallow Glycinate, Dimethiconepropyl Propyl of PG-Betaines, Erucamidopropyl Hydroxysultaine, hydrogenated sebum from Betaines, Isostearamidopropyl Betaine, Lauramidopropyl Betaine, Lauryl Hydroxysultaine, Laurylsultaine, Milkamidopropyl Betaine, Minkamidopropyl Betaine, Myristamidopropyl Betaine, Myristyl Betaine, Oleamidopropyl Betaine, Oleamidopropyl Hydroxysultaine, Oleyl Betaine, Olivamidopropyl Betaine, Palmamidopropyl Betaine, Palmitamidopropyl Betaine, Palmitoylcarnitine, Palm Kernelamidopropyl Betaine, Polytetrafluoroethylene Acetoxypropyl Betaine, Ricinoleam Idopropyl Betaine, Sesamidopropyl Betaine, Soyamidopropyl Betaine, Stearamidopropyl Betaine, Stearyl Betaine, Tallowamidopropyl Betaine, Tallowamidopropyl Betaine, Tallowamidopropyl Hydroxysultaine, Tallow of Betaines, Tallow of Betaines Dihydroxyethyl Betaines, undecylenamidopropylbetaines and wheat germamidopropylbetaines.

Preferred betaines are, for example, C12-C18 alkyl betaines and sulfobetaines. The zwitterionic surfactant is preferably a betaine surfactant, more preferably a cocoamidopropyl betaine surfactant.
Non-limiting examples of cationic surfactants - which can also be used in combinations of more than one other surfactant - include: the quaternary ammonium surfactants, which can have up to 26 carbon atoms, include: alkoxylated quaternary ammonium surfactants (AQA) as in US$6,136,769 discussed; dimethylhydroxyethyl quaternary ammonium, as in US$6,004,922 discussed; dimethylhydroxyethyllaurylammonium chloride; cationic polyamine surfactants, as used in WO 98/35002 , WO 98/35003 , WO 98/35004 , WO 98/35005 and WO 98/35006 discussed; cationic ester surfactants as described in U.S. Patent Nos. 4,228,042 , 4,239,660 , 4,260,529 and US$6,022,844 and amino surfactants as discussed in US$6,221,825 and WO 00/47708 are discussed, especially amidopropyldimethylamine (APA).

Compositions according to the invention can comprise at least one builder. In the context of the present invention, no distinction is made between constructors and those components which are referred to elsewhere as "co-builders". Examples of builders are complexing agents, also referred to below as complexing agents, ion exchangers and precipitants. The builders are selected from citrate, phosphates, silicates, carbonates, phosphonates, aminocarboxylates and polycarboxylates.
In the context of the present invention, the term citrate includes the mono- and dialkali metal salts and in particular the mono- and preferably the trisodium salt of citric acid, ammonium or substituted ammonium salts of citric acid and citric acid. Citrate can be used as an anhydrous compound or as a hydrate, for example as sodium citrate dihydrate. The citrate amounts are calculated with reference to anhydrous trisodium citrate.
The term phosphate includes sodium metaphosphate, sodium orthophosphate, sodium hydrogen phosphate, sodium pyrophosphate and polyphosphates such as sodium tripolyphosphate. Preferably, however, the composition according to the invention is free of phosphates and polyphosphates, which includes hydrogen phosphates, for example free of trisodium phosphate, pentasodium tripolyphosphate and hexasodium metaphosphate ("phosphate-free"). In connection with phosphates and polyphosphates, "free of" should be understood in the context of the present invention to mean that the total content of phosphate and polyphosphate is in the range from 10 ppm to 0.2% by weight of the respective composition, determined by gravimetry.
The term carbonates includes alkali metal carbonates and alkali hydrogen carbonates, with sodium salts being preferred. Na2CO3 is particularly preferred.
Examples of phosphonates are hydroxyalkanephosphonates and aminoalkanephosphonates. Among the hydroxyalkanephosphonates, 1-hydroxyethane-1,1-diphosphonate (HEDP) is of particular importance as a builder. It is preferably used as the sodium salt, with the disodium salt being neutral and the tetrasodium salt being alkaline (pH 9). Suitable aminoalkanephosphonates are preferably ethylenediaminetetramethylenephosphonate (EDTMP), diethylenetriaminepentamethylenephosphonate (DTPMP) and their higher homologues. They are preferably used in the form of the neutrally reacting sodium salts, e.g. as the hexasodium salt of EDTMP or as the hepta- and octa-sodium salts of DTPMP.

Examples of aminocarboxylates and polycarboxylates are nitrilotriacetates, ethylenediaminetetraacetate, diethylenetriaminepentaacetate, triethylenetetraaminehexaacetate, propylenediaminetetraacetic acid, ethanoldiglycines, methylglycine diacetate and glutamine diacetate. The term aminocarboxylates and polycarboxylates also includes their respective unsubstituted or substituted ammonium salts and the alkali metal salts such as the sodium salts, in particular of the respective fully neutralized compound.
Silicates in the context of the present invention include in particular sodium disilicate and sodium metasilicate, aluminosilicates such as zeolites and layered silicates, in particular those of the formula α-Na2Si2O5, β-Na2Si2O5 and δ-Na2Si2O5.
The compositions of the invention may contain one or more builders selected from materials not mentioned above. Examples of builders are α-hydroxypropionic acid and oxidized starch.
In one embodiment of the present invention, builder is selected from polycarboxylates. The term "polycarboxylates" includes non-polymeric polycarboxylates such as succinic acid, C2-C16 alkyl disuccinates, C2-C16 alkenyl disuccinates, ethylenediamine-N,N'-succinic acid, tartaric acid diacetate, alkali metal malonates, tartaric acid monoacetate, propanetricarboxylic acid, butanetetracarboxylic acid and cyclopentanetetracarboxylic acid.
Oligomeric or polymeric polycarboxylates are, for example, polyaspartic acid or, in particular, alkali metal salts of (meth)acrylic acid homopolymers or (meth)acrylic acid copolymers.
Suitable comonomers are monoethylenically unsaturated dicarboxylic acids such as maleic acid, fumaric acid, maleic anhydride, itaconic acid and citraconic acid. A suitable polymer is in particular polyacrylic acid, which preferably has a weight-average molecular weight Mw in the range from 2000 to 40,000 g/mol, preferably 2000 to 10,000 g/mol, in particular 3000 to 8000 g/mol. Other suitable copolymeric polycarboxylates are in particular those of acrylic acid with methacrylic acid and of acrylic acid or methacrylic acid with maleic acid and/or fumaric acid.
It is also possible to use copolymers of at least one monomer from the group consisting of monoethylenically unsaturated C3-C10 mono- or C4-C10 dicarboxylic acids or their anhydrides, such as maleic acid, maleic anhydride, acrylic acid, methacrylic acid, fumaric acid, itaconic acid and citraconic acid, with at least one hydrophilically or hydrophobically modified co-monomer as listed below.
Suitable hydrophobic comonomers are, for example, isobutene, diisobutene, butene, pentene, hexene and styrene, olefins with ten or more carbon atoms or mixtures thereof, such as 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, 1-docosene, 1-tetracosene and 1-hexacosene, C22-α-olefin, a mixture of C20-C24-α-olefins and polyisobutene with an average of 12 to 100 carbon atoms per molecule.
Suitable hydrophilic comonomers are monomers with sulfonate or phosphonate groups, as well as nonionic monomers with hydroxyl function or alkylene oxide groups. Examples include: allyl alcohol, isoprenol, methoxypolyethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, methoxypolybutylene glycol (meth)acrylate, methoxypoly(propylene oxide-co-ethylene oxide) (meth)acrylate, ethoxypolyethylene glycol (meth)acrylate, ethoxypolypropylene glycol (meth)acrylate, ethoxypolybutylene glycol (meth)acrylate and ethoxypoly(propylene oxide-co-ethylene oxide) (meth)acrylate. Polyalkylene glycols can comprise 3 to 50, in particular 5 to 40 and in particular 10 to 30 alkylene oxide units per molecule.
Particularly preferred monomers containing sulfonic acid groups are 1-acrylamido-1-propanesulfonic acid, 2-acrylamido-2-propanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, 2-methacrylamido-2-methylpropanesulfonic acid, 3-methacrylamido-2-hydroxypropanesulfonic acid, allylsulfonic acid, methallylsulfonic acid, allyloxybenzenesulfonic acid, methallyloxybenzenesulfonic acid, 2-hydroxy-3-(2-propenyloxy)propanesulfonic acid, 2-methyl-2-propen-1-sulfonic acid, styrenesulfonic acid, vinylsulfonic acid, 3-sulfopropyl acrylate, 2-sulfoethyl methacrylate, 3-sulfopropyl methacrylate, sulfomethacrylamide, sulfomethylmethacrylamide and salts of these acids, such as sodium, potassium or ammonium salts thereof.
Particularly preferred monomers containing phosphonate groups are vinylphosphonic acid and its salts.
In addition, amphoteric polymers can also be used as builders. Compositions according to the invention can, for example, contain a total of 0.1 to 70% by weight, preferably 10 to 50% by weight, preferably up to 20% by weight, of builders, particularly in solid formulations. Liquid formulations according to the invention preferably contain a builder in the range from 0.1 to 8% by weight.

The formulations according to the invention can comprise one or more alkali carriers. Alkali carriers ensure, for example, a pH of at least 9 if an alkaline pH is desired. Suitable examples are the above-mentioned alkali carbonates, alkali hydrogen carbonates and alkali metal metasilicates as well as alkali hydroxides. A preferred alkali metal is potassium, particularly preferably sodium. In one embodiment of the present invention, a pH of >7 is set using amines, preferably alkanolamines, particularly preferably triethanolamine.

In one embodiment of the present invention, the detergent formulation or composition according to the invention additionally comprises at least one enzyme.
Useful enzymes include, for example, one or more hydrolases selected from lipases, amylases, proteases, cellulases, hemicellulases, phospholipases, esterases, pectinases, lactases and peroxidases, as well as combinations of at least two of the aforementioned types.
In one embodiment, the composition according to the invention additionally comprises at least one enzyme.
Preferably, the at least one enzyme is a detergent enzyme.
In one embodiment, the enzyme is designated as oxidoreductase (EC1), transferase (EC2), hydrolase (EC3), Lyase (EC4), isomerase (EC5) or ligase (EC6) (EC numbering is according to Enzyme Nomenclature, Recommendations (1992) of the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology including its supplements published 1993-1999). Preferably, the enzyme is a hydrolase (EC3).
In a preferred embodiment, the enzyme is selected from the group consisting of proteases, amylases, lipases, cellulases, mannanases, hemicellulases, phospholipases, esterases, pectinases, lactases, peroxidases, xylanases, cutinases, pectate lyases, keratinases, reductases, oxidases, phenol oxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, beta-glucanases, arabinosidedases, hyaluronidases, chondroitinases, laccases, nucleases, DNases, phosphodiesterases, phytases, carbohydrases, galactanases, xanthanases, xyloglucanases, oxidoreductase, perhydrolases, aminopeptidase, Asparaginase, carbohydrase, carboxypeptidase, catalase, chitinase, cyclodextrin glycosyltransferase, alpha-galactosidase, beta-galactosidase, glucoamylase, alpha-glucosidase, beta-glucosidase, invertase, ribonuclease, transglutaminase and dispersins and combinations of at least two of the aforementioned types. The enzyme is particularly preferably selected from the group consisting of proteases, amylases, lipases, cellulases, mannanases, xylanases, DNases, dispersins, pectinases, oxidoreductases and cutinases and combinations of at least two of the preceding types. Most preferably the enzyme is a protease, preferably a serine protease, particularly preferably a subtilisin protease. Such enzymes may be incorporated into the composition in amounts sufficient to provide an effective amount to achieve a beneficial effect, preferably for primary washing effects and/or secondary washing effects such as anti-greying or anti-pilling effects (e.g. in the case of cellulases). Preferably, the enzyme is present in the composition at concentrations of from about 0.00001% to about 5%, preferably from about 0.00001% to about 2%, more preferably from about 0.0001% to about 1%, or even more preferably from about 0.001% to about 0.5% enzyme protein by weight of the composition. Preferably, the enzyme-containing composition further comprises an enzyme stabilization system.
Preferably, the enzyme-containing composition described herein comprises from about 0.001% to about 10%, from about 0.005% to about 8%, or from about 0.01% to about 6% by weight of the composition of an enzyme stabilization system. The enzyme stabilization system can be any stabilization system that is compatible with the enzyme.

Preferably, the enzyme stabilization system comprises at least one compound selected from the group consisting of polyols (preferably 1,3-propanediol, ethylene glycol, glycerin, 1,2-propanediol or sorbitol), salts (preferably CaCl2, MgCl2 or NaCl), short chain (preferably C1-C6) carboxylic acids (preferably formic acid, formate (preferably sodium formate), acetic acid, acetate or lactate), borate, boric acid, boronic acids (preferably, 4-formylphenylboronic acid (4-FPBA)), peptide aldehydes, peptide acetals and peptide aldehyde hydrosulfite adducts. Preferably, the enzyme stabilization system comprises a combination of at least two of the compounds selected from the group consisting of salts, polyols and short chain carboxylic acids, and preferably one or more of the compounds selected from the group consisting of borate, boric acid, boronic acids (preferably 4-formylphenylboronic acid (4-FPBA)), peptide aldehydes, peptide acetals and peptide aldehyde hydrosulfite adducts. In particular, when proteases are present in the composition, protease inhibitors may be added, preferably selected from borate, boric acid, boronic acids (preferably 4-FPBA), peptide aldehydes (preferably peptide aldehydes such as Z-VAL-H or Z-GAY-H), peptide acetals and peptide aldehyde hydrosulfite adducts. The compositions according to the invention may contain one or more bleaching agents (bleaching agents).
Preferred bleaching agents are selected from sodium perborate, anhydrous or, for example, as monohydrate or as tetrahydrate or so-called dihydrate, sodium percarbonate, anhydrous or, for example, as monohydrate, and sodium persulfate, where the term “persulfate” includes the salt of the peracid H2SO5 and also the peroxodisulfate.
The alkali metal salts can also be alkali metal hydrogen carbonate, alkali metal hydrogen perborate and alkali metal hydrogen persulfate. However, the dialkali metal salts are preferred.

The formulations according to the invention can comprise one or more bleach catalysts. Bleach catalysts can be selected from oxaziridinium-based bleach catalysts, bleach-enhancing transition metal salts or transition metal complexes such as manganese, iron, cobalt, ruthenium or molybdenum salen complexes or carbonyl complexes. Manganese, iron, cobalt, ruthenium, molybdenum, titanium, vanadium and copper complexes with nitrogen-containing tripod ligands as well as cobalt, iron, copper and ruthenium amine complexes can also be used as bleach catalysts.

Formulations according to the invention can comprise one or more bleach activators, e.g. tetraacetylethylenediamine, tetraacetylmethylenediamine, tetraacetylglycoluril, tetraacetylhexyldiamine, acylated phenolsulfonates such as e.g. n-nonanoyl or isononanoyloxybenzenesulfonates, N-methylmorpholinium acetonitrile salts ("MMA salts"), trimethylammonium acetonitrile salts, N-acylimides such as e.g. N-nonanoylsuccinimide, 1,5-diacetyl-2,2-dioxohexahydro-1,3,5-triazine ("DADHT") or nitrile quats (trimethylammonium acetonitrile salts).

The formulations according to the invention can comprise one or more corrosion inhibitors. In the present case, these are understood to mean compounds which inhibit the corrosion of metal. Examples of suitable corrosion inhibitors are triazoles, in particular benzotriazoles, bisbenzotriazoles, aminotriazoles, alkylaminotriazoles, and also phenol derivatives such as hydroquinone, pyrocatechol, hydroxyhydroquinone, gallic acid, phloroglucinol or pyrogallol.
In one embodiment of the present invention, formulations according to the invention contain a total of 0.1 to 1.5% by weight of corrosion inhibitor.

The formulations according to the invention can also comprise other cleaning polymers and/or soil release polymers.
Additional cleaning polymers may include “multifunctional polyethyleneimines” (e.g. Sokalan HP20 from BASF) and/or “multifunctional diamines” (e.g. Sokalan® HP96 from BASF) as well as the WO2021/254828 , WO2022/136408A1 , WO2022/136409A1 , WO2021/165468 , WO2023/021103 , WO2023/021104 , WO2023/021105 and WO2023/117494 disclosed and claimed. Such multifunctional polyethyleneimines are typically ethoxylated polyethyleneimines having a weight-average molecular weight Mw in the range from 3000 to 250000, preferably 5000 to 200000, particularly preferably 8000 to 100000, particularly preferably 8000 to 50000, particularly preferably 10000 to 30000 and very particularly preferably 10000 to 20000 g/mol. Suitable multifunctional polyethyleneimines have 80% to 99% by weight. Preferably 85% to 99% by weight, particularly preferably 90% to 98% by weight, very particularly preferably 93% to 97% by weight or 94% to 96% by weight of ethylene oxide side chains, based on the total weight of the materials. Ethoxylated polyethyleneimines are typically based on a polyethyleneimine core and a polyethylene oxide shell. Suitable polyethyleneimine core molecules are polyethyleneimines with a weight-average molecular weight Mw in the range from 500 to 5000 g/mol. A molecular weight of 500 to 1000 g/mol is preferably used, and an Mw of 600 to 800 g/mol is even more preferred. The ethoxylated polymer then has an average of 5 to 50, preferably 10 to 35 and even more preferably 20 to 35 ethylene oxide (EO) units per NH functional group.
Suitable multifunctional diamines are typically ethoxylated C2 to C12 alkylenediamines, preferably hexamethylenediamine, which are further quaternized and optionally sulfated. Typical multifunctional diamines have a weight-average molecular weight Mw in the range from 2000 to 10,000, particularly preferably 3000 to 8000 and most preferably 4000 to 6000 g/mol. In a preferred embodiment of the invention, ethoxylated hexamethylenediamine, further quaternized and sulfated, can be used, which contains on average 10 to 50, preferably 15 to 40 and even more preferably 20 to 30 ethylene oxide (EO) groups per NH-functional group and which preferably carries two cationic ammonium groups and two anionic sulfate groups.
In a preferred embodiment of the present invention, the cleaning agents may contain at least one multifunctional polyethyleneimine and/or at least one multifunctional diamine, in particular one of the claimed polymers of Sokalan HP20, Sokalan® HP96 and/or one of the WO2021/254828 , WO2022/136408A1 , WO2022/136409A1 , WO2021/165468 , WO2023/021103 disclosed and claimed polymers, WO2023/021104 , WO2023/021105 and or WO2023/117494 to improve the cleaning performance, such as preferably the stain removal ability, in particular the primary cleaning effect of particulate stains on polyester fabrics of detergents. The multifunctional polyethyleneimines or multifunctional diamines or mixtures thereof according to the above descriptions can be added to the detergents and cleaning agents in amounts of generally from 0.05 to 15 wt.%, preferably from 0.1 to 10 wt.% and particularly preferably from 0.25 to 5 wt.% and even up to 2 wt.%, based on the respective total composition, including other components and water and/or solvents.
Thus, one aspect of the present invention is a detergent composition, in particular a liquid detergent, comprising (i) at least one compound according to the invention and (ii) at least one compound selected from multifunctional polyethyleneimines and multifunctional diamines and mixtures thereof.
In one embodiment of the present invention, the ratio of the at least one compound according to the invention and (ii) the at least one compound selected from multifunctional Polyethylenimines and multifunctional diamines and mixtures thereof, 10:1 to 1:10, preferably from 5:1 to 1:5 and particularly preferably from 3:1 to 1:3.

• 4,4'-Dichlor-2-hydroxydiphenylether (weitere Bezeichnungen: 5-Chlor-2-(4-chlorphenoxy)phenol, Diclosan, DCPP), Tinosan® HP 100 (Handelsprodukt der BASF SE, das 30 % des antimikrobiell wirksamen 4,4'-Dichoro-2-hydroxydiphenylethers enthält); 2-Phenoxyethanol (weitere Bezeichnungen: Phenoxyethanol, Methylphenylglykol, Phenoxetyethanol, Ethylenglykolphenylether, Ethylenglykolmonophenylether, 2-(Phenoxy)ethanol, 2-Phenoxy-1-ethanol); 2-Brom-2-nitropropan-1,3-diol (weitere Bezeichnungen: 2-Brom-2-nitro-1,3-propandiol, Bronopol); Glutaraldehyd (weitere Bezeichnungen: 1-5-Pentandien, Pentan-1,5-Zifferblatt, Glutaral, GlutarDialdehyd); Glyoxal (weitere Namen: Ethandium, Oxylaldehyd, 1,2-Ethandium); 2-Butyl-benzo[d]isothiazol-3-on („BBIT“); 2-Methyl-2H-isothiazol-3-on („MIT“); 2-Octyl-2H-isothiazol-3-on („OIT“); 5-Chlor-2-methyl-2H-isothiazol-3-on („CIT“ oder „CMIT“); Gemisch aus 5-Chlor-2-methyl-2H-isothiazol-3-on („CMIT“) und 2-Methyl-2H-isothiazol-3-on („MIT“) (Gemisch aus CMIT/MIT); 1,2-Benzisothiazol-3(2H)-on („BIT“); Hexa-2,4-diensäure (Trivialname „Sorbinsäure“) und ihre Salze, z. B. Calciumsorb-at, Natriumsorbat; Kalium (E,E)-hexa-2,4-dienoat (Kaliumsorbat); Milchsäure und ihre Salze; L-(+)-Milchsäure; insbesondere Natriumlactat; Benzoesäure und Salze der Benzoesäure, z.B. Natriumbenzoat, Ammoniumbenzoat, Calciumbenzoat, Magnesiumbenzoat, MEA-Benzoat, Kaliumbenzoat; Salicylsäure und ihre Salze, z.B. Calciumsalicylat, Magnesiumsalicylat, MEA-Salicylat, Natriumsalicylat, Kaliumsalicylat, TEA-Salicylat; Benzalkoniumchlorid, Benzalkoniumbromid, Benzalkoniumsaccharinat; Didecyldimethylammoniumchlorid („DDAC“); N-(3-Aminopropyl)-N-dodecylpropan-1,3-diamin („Diamin“); Peressigsäure; Wasserstoffperoxid.

Cleaning agents, textile and household care products and in particular the detergent formulations comprising the compound according to the invention may also contain at least one antimicrobial agent (also called “preservative”).
An antimicrobial agent is a chemical compound that kills microorganisms or inhibits their growth or proliferation. Microorganisms can be bacteria, yeasts or molds. A preservative is an antimicrobial agent that can be added to aqueous products and compositions to maintain the original performance, properties and integrity of the products and compositions by killing contaminating microorganisms or inhibiting their growth.
The composition/formulation may contain one or more antimicrobial agents and/or preservatives as described in the patent WO2021/115912 A1 (“Formulations comprising a hydrophobically modified polyethyleneimine and one or more enzymes”) on pages 35 to 39.
The following antimicrobial agents and/or preservatives are of particular interest for cleaning agents and textile and household care products and especially for detergent formulations:

• 4,4'-dichloro-2-hydroxydiphenyl ether (other names: 5-chloro-2-(4-chlorophenoxy)phenol, diclosan, DCPP), Tinosan® HP 100 (commercial product of BASF SE, which contains 30% of the antimicrobially effective 4,4'-dichloro-2-hydroxydiphenyl ether); 2-phenoxyethanol (other names: phenoxyethanol, methylphenyl glycol, phenoxetyethanol, ethylene glycol phenyl ether, ethylene glycol monophenyl ether, 2-(phenoxy)ethanol, 2-phenoxy-1-ethanol); 2-bromo-2-nitropropane-1,3-diol (other names: 2-bromo-2-nitro-1,3-propanediol, bronopol); Glutaraldehyde (other names: 1-5-pentandiene, pentane-1,5-dial, glutaral, glutardialdehyde); glyoxal (other names: ethandium, oxyaldehyde, 1,2-ethandium); 2-butyl-benzo[d]isothiazol-3-one (“BBIT”); 2-methyl-2H-isothiazol-3-one (“MIT”); 2-octyl-2H-isothiazol-3-one (“OIT”); 5-chloro-2-methyl-2H-isothiazol-3-one (“CIT” or “CMIT”); mixture of 5-chloro-2-methyl-2H-isothiazol-3-one (“CMIT”) and 2-methyl-2H-isothiazol-3-one (“MIT”) (mixture of CMIT/MIT); 1,2-benzisothiazol-3(2H)-one (“BIT”); Hexa-2,4-dienoic acid (common name "sorbic acid") and its salts, e.g. calcium sorbate, sodium sorbate; potassium (E,E)-hexa-2,4-dienoate (potassium sorbate); lactic acid and its salts; L-(+)-lactic acid; in particular sodium lactate; benzoic acid and salts of benzoic acid, e.g. sodium benzoate, ammonium benzoate, calcium benzoate, magnesium benzoate, MEA benzoate, potassium benzoate; salicylic acid and its salts, e.g. calcium salicylate, magnesium salicylate, MEA salicylate, sodium salicylate, potassium salicylate, TEA salicylate; benzalkonium chloride, benzalkonium bromide, benzalkonium saccharinate; didecyldimethylammonium chloride ("DDAC"); N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine ("diamine"); peracetic acid; Hydrogen peroxide.

At least one antimicrobial agent or preservative may be added to the composition of the invention in a concentration of 0.001 to 10% based on the total weight of the composition.
Preferably, the composition contains 2-phenoxyethanol in a concentration of 0.1 to 2% or 4,4'-dichloro-2-hydroxydiphenyl ether (DCPP) in a concentration of 0.005 to 0.6%.
The invention also includes a method for preserving an aqueous composition according to the invention against microbial contamination or growth, which method comprises adding at least one antimicrobial agent or preservative, preferably 2-phenoxyethanol.
The invention also encompasses a method for providing an antimicrobial effect to textiles after treatment with a solid detergent (e.g. powder, granules, capsules, tablets, bars, etc.), a liquid detergent, a fabric softener or a rinse containing 4,4'-dichloro-2-hydroxydiphenyl ether (DCPP).

The formulations according to the invention may also comprise water and/or additional organic solvents, e.g. ethanol or propylene glycol.

Other optional ingredients may include viscosity modifiers, cationic surfactants, foam enhancing or reducing agents, fragrances, dyes, optical brighteners and dye transfer inhibitors.

Compositions for dishwashing detergents

Another aspect of the present invention is also a dishwashing composition comprising at least one compound(s) according to the invention as described above.

Thus, one aspect of the present invention is also the use of the compound(s) of the invention as described above in dishwashing applications, such as manual or automated dishwashing applications.

Dishwashing detergents according to the invention may be in the form of a liquid, semi-liquid, cream, lotion, gel or solid composition, with solid embodiments including, for example, powders and tablets. Liquid compositions are typically preferred for manual dishwashing applications, while solid formulations and sachet formulations (where the sachets may contain solids in addition to liquid ingredients) are typically preferred for automated dishwashing detergents; however, in some regions of the world, liquid automated dishwashing detergents are also used and thus naturally also fall within the term "dishwashing detergent".

The dishwashing detergents are intended for direct or indirect application to dishes and metal and glass surfaces such as drinking and other glasses, cups, dishes and cookware such as pots and pans as well as cutlery such as forks, spoons, knives and the like.
The method according to the invention for cleaning dishware, metal and/or glass surfaces comprises the step of applying the dishwashing detergent, preferably in liquid form, to the surface, either directly or by means of a cleaning device, i.e. in pure form. The composition is applied directly to the surface to be treated and/or to a cleaning device or cleaning device, such as a dishcloth, sponge or dishwashing brush and the like, without being subjected to any major dilution (immediately) before application. The cleaning device or cleaning device is preferably moistened before or after the composition is delivered to it. In the method according to the invention, the composition can also be applied in diluted form.

Both pure and diluted use result in superior cleaning performance, i.e. the formulations according to the invention, which contain at least one compound(s) according to the invention, have excellent degreasing properties. The effort required to remove greasy and/or oily soiling from the dishes, metal and/or glass surfaces is reduced by the presence of the compound(s) according to the invention, even if the surfactant content used is lower than in conventional compositions.

Preferably, the composition is formulated to provide excellent grease cleaning (degreasing) properties, long lasting suds and/or improved viscosity control at reduced temperature exposures; Preferably, at least two, more preferably all three properties are present in the dishwashing composition of the invention. Optional - preferably present - further benefits of the manual dishwashing composition of the invention include soil removal, shine and/or hand care; More preferably, at least two, and most preferably all three further benefits are present in the dishwashing composition of the invention.

In one embodiment of the present invention, the compound(s) of the invention is a component of a manual dishwashing formulation which additionally comprises at least one surfactant, preferably at least one anionic surfactant.

In another embodiment of the present invention, the compound(s) of the invention is a component of a manual dishwashing formulation which additionally comprises at least one anionic surfactant and at least one further surfactant, preferably selected from amphoteric surfactants and/or zwitterionic surfactants. In a preferred embodiment of the present invention, the manual dishwashing formulations contain at least one amphoteric surfactant, preferably an amine oxide, or at least one zwitterionic surfactant, preferably a betaine, or mixtures thereof to assist the foaming, cleaning power and/or mildness of the detergent composition.

Examples of suitable anionic surfactants are already mentioned above for fabric detergent compositions.
Preferred anionic surfactants for dishwashing detergents are selected from C10-C15 linear alkylbenzenesulfonates, C10-C18 alkyl ether sulfates with 1-5 ethoxy units and C10-C18 alkyl sulfates.
Preferably, the formulation of the manual dishwashing detergent according to the invention comprises at least 1 wt.% to 50 wt.%, preferably in the range of greater than or equal to about 3 wt.% to equal to or less than about 35 wt.%, particularly preferably in the range of greater than or equal to 5 wt.% to less than or equal to 30 wt.%, and most preferably in the range of greater than or equal to 5 wt.% to less than or equal to 20 wt.% of one or more anionic surfactants as described above, based on the respective total composition, including other components and water and/or solvents.

Dishwashing detergents according to the invention can contain at least one amphoteric surfactant. Examples of suitable amphoteric surfactants for dishwashing detergents have already been mentioned above for detergent compositions.
Preferred amphoteric surfactants for dishwashing detergents are selected from C8-C18 alkyl dimethylamine oxides and C8-C18 alkyl di(hydroxyethyl)amine oxide.
The hand dishwashing detergent composition of the invention preferably comprises from 1% to 15%, preferably from 2% to 12%, more preferably from 3% to 10% by weight of the composition of an amphoteric surfactant, preferably an amine oxide surfactant. Preferably, the composition of the invention comprises a mixture of the anionic surfactants and alkyldimethylamine oxides in a weight ratio of less than about 10:1, more preferably less than about 8:1, more preferably from about 5:1 to about 2:1. The addition of the amphoteric surfactant provides good foaming properties in the detergent composition.

Dishwashing detergents according to the invention can contain at least one zwitterionic surfactant.
Examples of suitable zwitterionic surfactants for dishwashing detergents are already mentioned above for detergent compositions.
Preferred zwitterionic surfactants for dishwashing detergents are selected from betaine surfactants, more preferably from cocoamidopropyl betaine surfactants.

In a preferred embodiment of the present invention, the zwitterionic surfactant is cocamidopropyl betaine.
The hand dishwashing detergent composition according to the invention optionally comprises 1% to 15%, preferably 2% to 12%, particularly preferably 3% to 10% by weight of the composition of a zwitterionic surfactant, preferably a betaine surfactant.

Dishwashing detergents according to the invention can contain at least one cationic surfactant. Examples of suitable cationic surfactants for dishwashing detergents have already been mentioned above for detergent compositions.
Cationic surfactants, when present in the composition, are present in an effective amount, more preferably from 0.1% to 5%, preferably 0.2% to 2% by weight of the composition.

Dishwashing detergents according to the invention can contain at least one non-ionic surfactant. Examples of suitable non-ionic surfactants for dishwashing detergents have already been mentioned above for detergents.
Preferred nonionic surfactants are the condensation products of Guerbet alcohols with 2 to 18 moles, preferably 2 to 15, more preferably 5 to 12, of ethylene oxide per mole of alcohol. Other preferred nonionic surfactants for use herein include fatty alcohol polyglycol ethers, alkyl polyglucosides and fatty acid glucamides.
The hand dishwashing detergent composition according to the invention can contain 0.1% to 10%, preferably 0.3% to 5%, particularly preferably 0.4% to 2% by weight of the composition of a linear or branched C10-alkoxylated nonionic surfactant having an average degree of alkoxylation of 2 to 6, preferably 3 to 5. Preferably, the linear or branched C10-alkoxylated nonionic surfactant is a branched C10-ethoxylated nonionic surfactant having an average degree of ethoxylation of 2 to 6, preferably 3 to 5. Preferably, the composition comprises 60% to 100%, preferably 80% to 100%, particularly preferably 100% by weight of the total linear or branched C10-alkoxylated nonionic surfactant of the branched C10-ethoxylated nonionic Surfactant. The linear or branched C10 alkoxylated nonionic surfactant is preferably a 2-propylheptylethoxylated nonionic surfactant with an average degree of ethoxylation of 3 to 5. A suitable 2-propylheptylethoxylated nonionic surfactant with an average degree of ethoxylation of 4 is Lutensol® XP40, commercially available from BASF SE, Ludwigshafen, Germany. The use of a 2-propylheptylethoxylated nonionic surfactant with an average degree of ethoxylation of 3 to 5 results in improved foam values and long-lasting foams.
Thus, one aspect of the present invention is a manual dishwashing detergent composition, in particular a liquid manual dishwashing detergent composition, comprising (i) at least one esteramine according to the invention and/or its salt and (ii) at least one further 2-propylheptylethoxylated nonionic surfactant having an average degree of ethoxylation of 3 to 5.

Dishwashing detergents according to the invention can contain at least one hydrotrope in an effective amount to ensure compatibility of the liquid hand dishwashing detergent compositions with water.

Suitable hydrotropes for use herein include anionic hydrotropes, particularly sodium, potassium and ammonium xylenesulfonate, sodium, potassium and ammonium toluenesulfonate, sodium, potassium and ammonium cumenesulfonate and mixtures thereof and related compounds as in US Patent 3,915,903 disclosed.
The liquid hand dishwashing compositions of the invention typically comprise from 0.1% to 15% by weight of the total liquid detergent composition of a hydrotrope or mixtures thereof, preferably from 1% to 10%, most preferably from 2% to 5% by weight of the total liquid manual dishwashing composition.

Dishwashing detergents according to the invention can contain at least one organic solvent.
Examples of organic solvents are C4-C14 ethers and diethers, glycols, alkoxylated glycols, C6-C16 glycol ethers, alkoxylated aromatic alcohols, aromatic alcohols, aliphatic branched alcohols, alkoxylated aliphatic branched alcohols, alkoxylated linear C1-C5 alcohols, linear C1-C5 alcohols, amines, C8-C14 alkyl and cycloalkyl hydrocarbons and halogenated hydrocarbons, and mixtures thereof.
When present, the liquid dishwashing detergents contain from 0.01% to 20%, preferably from 0.5% to 15%, more preferably from 1% to 10%, most preferably from 1% to 5%, by weight of the liquid detergent composition of a solvent. These solvents may be used in conjunction with an aqueous liquid carrier, such as water, or they may be used without an aqueous liquid carrier being present. In systems with higher solvents, the absolute values of viscosity may decrease, but there is a local maximum point in the viscosity profile.

The dishwashing compositions contained herein may further comprise from 30% to 90% by weight of an aqueous liquid carrier comprising water in which the other essential and optional ingredients are dissolved, dispersed or suspended. More preferably, the compositions of the invention comprise from 45% to 85%, even more preferably from 60% to 80% by weight of the aqueous liquid carrier. However, the aqueous liquid carrier may also contain other materials which are liquid at room temperature (25°C) or which dissolve in the liquid carrier and which may serve another function besides that of an inert filler.

Dishwashing detergents according to the invention can contain at least one electrolyte. Suitable electrolytes are preferably selected from inorganic salts, even more preferably selected from monovalent salts, very particularly preferably sodium chloride.
The liquid hand dishwashing detergents according to the invention can contain 0.1% to 5%, preferably 0.2% to 2% by weight of the composition of an electrolyte.

Manual dishwashing formulations containing the esteramine and/or its salt(s) of the invention may also contain at least one antimicrobial agent.
Examples of suitable antimicrobial agents for dishwashing detergents are already mentioned above for detergent compositions.
The antimicrobial agent can be added to the hand dishwashing detergent according to the invention in a concentration of 0.0001% to 10% by weight based on the total weight of the composition. Preferably, the formulation contains 2-phenoxyethanol in a concentration of 0.01% to 5% by weight, particularly preferably 0.1% to 2% by weight and/or 4,4'-dichloro-2-hydroxydiphenyl ether in a concentration of 0.001% to 1% by weight, particularly preferably 0.002% to 0.6% by weight (in all cases based on the total weight of the composition).

Other additional ingredients include conditioning polymers, cleaning polymers, surface modifying polymers, soil flocculation polymers, rheology modifying polymers, enzymes, structuring agents, builders, chelating agents, cyclic diamines, plasticizers, humectants, skin rejuvenating agents, carboxylic acids, detergent particles, bleaching agents and bleach activators, fragrances, odor control agents, pigments, dyes, opacifiers, pearls, pearlescent particles, microcapsules, antibacterial agents, pH adjusters including NaOH and alkanolamines such as monoethanolamines and buffering agents.

General cleaning products and laundry formulations

The liquid formulations disclosed in this chapter can and will preferably contain from 0 to 2% 2-phenoxyethanol, preferably about 1%, in addition to any other ingredients mentioned.
The liquid formulations disclosed above and below can and will preferably contain 0-0.2% 4,4'-dichoro-2-hydroxydiphenyl ether, preferably about 0.15%, in addition to all other recited ingredients. The bleach-free solid detergent compositions can contain 0-0.2% 4,4'-dichoro-2-hydroxydiphenyl ether, preferably about 0.15%, in addition to all other recited ingredients.
The disclosed formulations in this chapter may and will preferably comprise one or more enzymes selected from the enzymes disclosed above, particularly preferably a protease and/or an amylase, wherein even more preferably the protease is a protease having at least 90% sequence identity to SEQ ID NO: 22 of EP1921147B1 and has the amino acid substitution R101 E (according to BPN' numbering) and wherein the amylase is an amylase with at least 90% sequence identity 54 of WO2021032881A1 wherein such enzymes are preferably present in the formulations at concentrations of from about 0.00001% to about 5%, preferably from about 0.00001% to about 2%, more preferably from about 0.0001% to about 1%, or even more preferably from about 0.001% to about 0.5% by weight of the composition.

The tables in this chapter show general cleaning compositions of certain types corresponding to typical compositions that correlate with typical washing conditions typically used in various regions and countries of the world. The at least one compound of the invention can be added to such formulations in suitable amounts as described herein.

If no inventive compound is added, a formulation shown is a "comparative" formulation; if the amount chosen is within the general range disclosed herein, and specifically within ranges disclosed herein as preferred amounts for the various ingredients and the inventive compound, the formulation is an inventive formulation. Ingredients (other than the inventive compound) listed with amounts that include "zero%" in the stated range may, but are not necessarily present in both the inventive and comparative formulations. Therefore, any number encompassed by a given range is intended to be included in the formulations shown in this section, and all possible variations and permutations are also intended to be included.

In a preferred embodiment, the compound according to the invention is used in a detergent.

Liquid detergents according to the present invention consist of: 0.1 - 5% at least one compound according to the invention 1-50% of surfactants 0.1-40% of builders, cobuilders and/or chelating agents 0.1-50% Other additions Water to add 100%.

Preferred liquid detergents according to the present invention are composed of: 0.5 - 2% at least one compound according to the invention 5-40% of anionic surfactants selected from C10-C15 LAS and C10-C18 alkyl ether sulfates with 1-5 ethoxy units 1.5 - 10% Ethoxy units non-ionic surfactants selected from C10-C18 alkyl ethoxylates with 3 - 10 2-20% of soluble organic builders/cobuilders selected from C10-C18 fatty acids, di- and tricarboxylic acids, hydroxy-di- and hydroxytricaboxylic acids, aminopolycarboxylates and polycarboxylic acids 0.05 - 5% an enzyme system containing at least one enzyme suitable for use as a cleaning agent and preferably also an enzyme stabilization system 0.5 - 20% of mono- or diols selected from ethanol, isopropanol, ethylene glycol or propylene glycol 0.1-20% Other additions Add water to 100%.

Solid detergents (such as powders, granules or tablets) according to the present invention consist of: 0.1 - 5% at least one compound according to the invention 1-50% of surfactants 0.1 - 90% of builders, cobuilders and/or chelating agents 0 - 50% of fillers 0-40% of bleaching agents 0.1-30% of other additives and/or water where the sum of the ingredients adds up to 100%.

Preferred solid detergents according to the present invention are composed of: 0.5 - 2% at least one compound according to the invention 5-30% anionic surfactants selected from C10-C15-LAS, C10-C18-alkyl sulfates and C10-C18-alkyl ether sulfates with 1-5 ethoxy units 1.5 - 7.5% of nonionic surfactants selected from C10-C18 alkyl ethoxylates with 3 - 10 ethoxy units 20-80% of inorganic builders and fillers selected from sodium carbonate, sodium bicarbonate, zeolites, soluble silicates, sodium sulfate 0.5 - 15% of cobuilders selected from C10-C18 fatty acids, di- and tricarboxylic acids, hydroxydi- and hydroxytricarboxylic acids, aminopolycarboxylates and polycarboxylic acids 0.1 - 5% an enzyme system containing at least one enzyme suitable for use as a cleaning agent and preferably also an enzyme stabilization system 0.5-30% of bleaching agents 0.1-20% Other additions Water to AD up to 100%

In a preferred embodiment, at least one esteramine and/or salt thereof according to the present invention is used in a manual dishwashing detergent.

Liquid manual dishwashing detergents according to the present invention consist of: 0.05 - 10% of at least one esteramine according to the invention and/or salt thereof 1-50% of surfactants 0.1-50% other additions Water to add 100%.

Preferred liquid manual dishwashing detergents of this present invention consist of: 0.2 - 5% of at least one esteramine according to the invention and/or salt thereof 5-40% of anionic surfactants selected from C10-C15 LAS, C10-C18 alkyl ether sulfates with 1-5 ethoxy units, and C10-C18 alkyl sulfate 2 10% of Cocamidopropyl Betaine 0-10% of Lauraminoxid 0-2% a non-ionic surfactant, preferably a C10 Guerbet alcohol alkoxylate 0-5% an enzyme, preferably amylase, and preferably also an enzyme stabilization system 0.5 - 20% of mono- or diols selected from ethanol, isopropanol, ethylene glycol or propylene glycol 0.1-20% Other additions Add water to 100%

In the following tables:

“Compound(s) of the invention” = at least one esteramine and/or a salt thereof as described in this present invention

General formula for detergent compositions according to the invention: Numbers: % by weight component Assortments of ingredients in liquid frame formulations Linear alkylbenzenesulfonic acid 0 to 30 Coconut fatty acid 1 to 12 Fatty alcohol ether sulfate 0 to 25 NaOH or mono- or triethanolamine Add to pH 7.5 to pH 9.0 Alcohol ethoxylate 3 to 10 1,2-propylene glycol 1 to 10 Ethanol 0 to 4 Sodium citrate 0 to 8 Water Up to 100

Inventive liquid laundry frame formulations: active (Figures: wt.% active) formula 1 F2 F3 F4 F5 F6 Alcohol Ethoxylate 7EO 5.40 10.80 12.40 7.30 1.60 7.60 Coconut fatty acid K12-18 2.40 3.10 3.20 3.20 3.50 6.40 Fatty alcohol ether sulfate 5.40 8.80 7.10 7.10 5.40 14.00 Linear alkylbenzenesulfonic acid 5.50 0.00 14.50 15.50 10.70 0.00 1,2 Propanediol 6:00 am 3.50 8.70 8.70 1.10 7.80 Triethanolamine 0 0 0 0 0 0 Monoethanolamine 0 0 4.00 4.30 0.30 0 NaOH 2.20 1.10 0 0 0 1.00 Glycerine 0 0.80 3.00 2.80 0 0 Ethanol 2.00 0 0 0 0.38 0.39 Nacitrate 3.00 2.80 3.40 2.10 7.40 5.40 Inventive connection(s) (total) 0.1 - 5 0.1 - 5 0.1 - 5 0.1 - 5 0.1 - 5 0.1 - 5 Polymers 0-10 0-10 0-10 0-10 0-10 0-10 At least one enzyme (each) 0-1 0-1 0-1 0-1 0-1 0-1 Water until 100 until 100 until 100 until 100 until 100 until 100

Liquid laundry frame formulations according to the invention - continued: active (Figures: wt.% active) F7 F8 F9 F10 F11 F12 F13-BOX F14 Alcohol Ethoxylate 7EO 3.80 0.30 13.30 8.00 5.70 8:00 pm 9.20 29.00 Coconut fatty acid K12-18 2.80 3.00 1.70 1.80 2.50 5.00 8.60 10.40 Fatty alcohol ether sulfate 2.80 4.50 3.90 4.10 0 10.00 22.20 0 Linear alkylbenzenesulfonic acid 6.30 5.43 11.45 5.90 10.10 10.00 28.00 27.00 1,2 Propanediol 0.50 0 2.50 0.40 6:00 am 10.00 7:00 7:00 Triethanolamine 0 0 0 8.10 0 0 0 0 Monoethanolamine 0.40 1.80 0 0 0 0 8.00 7:00 NaOH 0 0 2.20 0 3.30 1.50 0 0 Glycerine 0 0.60 0.20 1.90 0 0 7:00 10.00 Ethanol 0 0 1.84 0 0 0 0 0 Nacitrate 4.60 3.30 3.30 1.40 0 1.50 0 0 Compound(s) according to the invention (total) 0.5 - 2 0.5 - 2 0.5 - 2 0.5 - 2 0.5 - 2 0.5 - 2 0.5 - 2 0.5 - 2 Polymers 0 - 10 0 - 10 0 - 10 0 - 10 0 - 10 0 - 10 0 - 10 0 - 10 At least one enzyme (each) 0 - 1 0 - 1 0 - 1 0 - 1 0 - 1 0 - 3 0 - 3 0 - 3 Water until 100 until 100 until 100 until 100 until 100 until 100 until 100 until 100

Washing powder frame formulations according to the invention: Active ingredients (numbers: wt.% active) Bleach-free powder Alcohol ethoxylate 7EO 0.6 0 1 0 0 5.2 Coconut fatty acid K12-18 1.2 0 0 0 0 0 Fatty alcohol ether sulfate 1.5 0 0 0 0 6 Linear alkylbenzenesulfonic acid 12.1 11.2 13.6 21.9 18.7 12.7 Bleach activator 0 0 0 0 0 0 Percarbonat 0 0 0 0 0 0 AcetateNa 0 0 0 0.1 0 0.1 CitrateNa 0 0 0 0 0 14 Na-silicate 27.9 5.8 6.6 2 15 20.3 Na-carbonate 17.2 35 37.3 30.1 37 1 Na-phosphate 0 0 0 14 0.3 0 Na hydrogen carbonate 0.7 0.9 0.5 2.7 0.4 10.5 Zeolite4A 4.2 0.1 5.1 10.2 1.8 11.6 HEDP 0 0 0 0 0 0.13 MGDA 0 1.1 0 0 0 0 at least one enzyme (each) 0 - 1.5 0 - 1.5 0 - 1.5 0 - 1.5 0 - 1.5 0 - 1.5 Na-sulfate 30.8 1.3 33 11 22 3 Na chloride 0.2 43 0.1 0 0.1 0.1 optical brightener 0.02 0 0.1 0.06 Inventive connection(s) (total) 0.2 - 5 0.2 - 5 0.2 - 5 0.2 - 5 0.2 - 5 0.2 - 5 Polymers 0 - 10 0 - 10 0 - 10 0 - 10 0 - 10 0 - 10

Washing powder frame formulations according to the invention - continued: Active ingredients (numbers: wt.% active) Powder containing bleach Alcohol ethoxylate 7EO 1.2 5 4 0.5 0.5 0 Coconut fatty acid K12-18 0 0 0 0.3 0 0.6 Fatty alcohol ether sulfate 0 3.9 4.4 1.6 0 0 Linear alkylbenzenesulfonic acid 7.6 12.1 11.5 12.2 6.5 10.4 Bleach activator 0.2 9.5 9.5 0.5 0.8 2.2 Percarbonat 3.6 19.4 16.6 2.2 11.5 5.8 AcetateNa 0 6.7 7.1 0.3 1 0.7 CitrateNa 0 1.6 8.2 0.3 0.9 1.7 Na-silicate 3.6 11.3 16.4 10.2 9.1 16.5 Na-carbonate 21.6 8.7 1.4 8th 22.9 14.8 Na Phosphate 0 0 0 0 0 0 Na hydrogen carbonate 0.2 2.8 1.6 0.8 0.5 0.5 Zeolite4A 1.6 1.4 2.4 1.6 1.8 2.3 HEDP 0 0.27 0.16 0 0 0.17 MGDA 0 0 0 0 0 0 At least one enzyme (each) 0-1.5 0-1.5 0-1.5 0-1.5 0-1.5 0-1.5 Na-sulfate 51 4 6 57 38 37 Na chloride 1 1 0.5 1.2 0.2 1 optical brightener 0.29 0.1 0.23 0.13 0.19 Inventive connection(s) (total) 0.5-2 0.5-2 0.5-2 0.5-2 0.5-2 0.5-2 Polymers 0-10 0-10 0-10 0-10 0-10 0-10

Other typical liquid detergent formulations LD1, LD2 and LD3 are listed in the following three tables: (Figures: wt% active)

Liquid detergent 1- LD1 “excellent” detergent; Formulation of liquid detergents Sodium alkylbenzenesulfonic acid (C10-C13) LAS 9.5 C13/C15 oxo alcohol reacted with 7 moles of EO 4.5 1,2 Propylene glycol 6 Ethanol 2 Potassium Coconut Soap 2.4 NaOH 2.2 Lauryl ether sulfate (Texapon) 5.0 Sodium citrate 3 Sokalan HP 20 2 Compound or comparison according to the invention 0.5-5 Graft polymer* 0-2 Water until 100

Liquid detergent 2- LD2 “medium” heavy-duty detergents Formulation of liquid detergents Sodium alkylbenzenesulfonic acid (C10-C13) 5.5 C13/C15 oxo alcohol reacted with 7 moles of EO 5.4 1,2 Propylene glycol 6 Ethanol 2 Potassium Coconut Soap 2.4 Monoethanolamine 2.5 Lauryl ether sulfate 5.4 Sodium citrate 3 Sokalan HP96 2 Compound or comparison according to the invention 0.1-4 Graft polymer* 0-2 Water until 100

Liquid detergent 3- LD3 “medium” performance “bio-based” detergent Formulation of liquid detergents MGDA 5.5 APG, branched C13-glucoside 3.5 1,2 Propylene glycol 6 Ethanol 2 Potassium Coconut Soap 4.4 NaOH 2.2 Lauryl ether sulfate 9.5 Sodium citrate 3 Compound or comparison according to the invention 0.1-4 Graft polymer* 0-2 Water until 100

All three previous tables for LD1, LD2, LD3: *"Graft polymer" = (polyethylene glycol of Mn 6000 g/mol as graft base, grafted with 40 wt.% vinyl acetate (based on the total polymer weight; prepared according to the general disclosure of WO2007138054A1 )

Formulations according to the invention for liquid manual dishwashing frames: Ingredients MDW.1 MDW.2 MDW.3-CARTON MDW.4-CARTON MDW.5-CARTON MDW.6-CARTON MDW.7-CARTON MDW.8-CARTON Linear C12-C14 alkylbenzenesulfonic acid 8th 0 6 0 6 0 6 0 C12-C14 fatty alcohol × 2 EO sulfate 8th 16 6 12 6 12 6 12 Cocamidopropyl betaine: 0 0 4 4 0 0 2 2 Lauramine oxide 0 0 0 0 4 4 2 2 2-Propylheptanol × 4 EO 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Inventive connection(s) (total) 0.5-5 0.5-5 0.5 - 5 0.5 - 5 0.5-5 0.5 - 5 0.5-5 0.5-5 Ethanol 2 2 2 2 2 2 2 2 Polymer(s) 0-5 0-5 0-5 0-5 0-5 0-5 0-5 0-5 2-Phenoxyethanol (preservative) 1 1 1 1 1 1 1 1 Sodium chloride 1 1 1 1 1 1 1 1 Demin. Water Add 100 Add 100 Add 100 Add 100 Add 100 Add 100 Add 100 Add 100 Sodium hydroxide add pH 8 addpH 8 addpH 8 addpH 8 addpH 8 addpH 8 addpH 8 addpH 8

It is preferred that within the respective detergent, cleaning composition and/or fabric and household care product, the at least one esteramine and/or salt thereof as described in this invention is present in a concentration of from about 0.1% to about 10%, preferably from about 0.2% to 5%, particularly preferably from about 0.5% to about 5%. all with respect to the Total weight of such composition or article in relation to the total weight of that composition or article and all numbers therebetween, including all ranges resulting from the selection of any of the said lower limits, including further 0.2, 0.3, 0.4, 1, 1.5, 2, 2.5, 3, 3.5 and 4 and combing with any of the said upper limits, including 19, 18, 17, 16, 14, 13, 12, 11, 9, 8, 7 and 6.

The specific embodiments as described in this disclosure are included in the present invention as part of this invention; the various other options disclosed in this present description as "optional", "preferred", "more preferred", "even more preferred" or "most preferred" may be individually and independently selected (unless such independent selection is not possible due to the nature of that feature or when such independent selection is expressly excluded) and then combined within any of the other embodiments (with other such options and preferences also being individually and independently selected), each and all such possible combinations being included as part of this invention as individual embodiments,
and in particular with the preferred embodiments disclosed in the following section.

Preferred embodiments

Embodiment 1

• i) mindestens einen Alkohol, der mindestens eine Hydroxygruppe trägt, wobei gegebenenfalls mindestens eine Hydroxygruppe in einem Schritt vor Schritt a) mit mindestens einem Alkylenoxid, bevorzugt mindestens 1 und bis zu 200, bevorzugt 1 bis 100, besonders bevorzugt bis zu 50 Mol Alkylenoxid pro Hydroxygruppe alkoxyliert werden kann,
• ii) mindestens ein Lacton und/oder (bevorzugt oder) Hydroxysäure, besonders bevorzugt nur Lacton,
• iii) mit mindestens einem Lactam und/oder (bevorzugt oder) mindestens einer Aminosäure, besonders bevorzugt nur Lactam, und
• iv) eine anorganische oder organische Säure, wobei die organische oder anorganische Säure vorzugsweise einen pKa-Wert im Bereich von -3 und bis +5, besonders bevorzugt von -2,5 bis 1,5 aufweist, bevorzugt organische Säure, besonders bevorzugt Sulfonsäuren, noch mehr bevorzugt Alkansulfonsäure und/oder Arylsulfonsäure, besonders bevorzugt Alkansulfonsäure, ganz besonders bevorzugt Methansulfonsäure,

worin das molare Verhältnis von
Komponente C (Lactam) bis Komponente D (Säure) in einem Bereich von 1:0,9 bis 1:1,5, bevorzugt etwa 1:0,95 bis 1:1,1 und besonders bevorzugt 1:1 bis 1:1,08 und ganz besonders bevorzugt etwa 1:1,02 wie genau 1:1,02 liegt, und
Komponente C (Lactam) pro Hydroxygruppe in Komponente A (Alkohol) höchstens 1:1, vorzugsweise Komponente C kleiner als gleich pro Hydroxygruppe in Komponente A (Alkohol), und Komponente B (Lacton/Hydroxysäure) pro Hydroxygruppe in Komponente A (Alkohol) von 1:0,1 bis 1:10.Esteramine and its salt, obtainable by a process comprising the step of reacting A + B + C in the presence of D with

• i) at least one alcohol which carries at least one hydroxyl group, where optionally at least one hydroxyl group can be alkoxylated in a step prior to step a) with at least one alkylene oxide, preferably at least 1 and up to 200, preferably 1 to 100, particularly preferably up to 50 mol of alkylene oxide per hydroxyl group,
• ii) at least one lactone and/or (preferably or) hydroxy acid, particularly preferably only lactone,
• iii) with at least one lactam and/or (preferably or) at least one amino acid, particularly preferably only lactam, and
• iv) an inorganic or organic acid, wherein the organic or inorganic acid preferably has a pKa value in the range from -3 to +5, particularly preferably from -2.5 to 1.5, preferably organic acid, particularly preferably sulfonic acids, even more preferably alkanesulfonic acid and/or arylsulfonic acid, particularly preferably alkanesulfonic acid, very particularly preferably methanesulfonic acid,

where the molar ratio of
Component C (lactam) to component D (acid) in a range of 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1 and particularly preferably 1:1 to 1:1.08 and most preferably about 1:1.02, such as exactly 1:1.02, and
Component C (lactam) per hydroxy group in component A (alcohol) at most 1:1, preferably component C less than or equal to per hydroxy group in component A (alcohol), and component B (lactone/hydroxy acid) per hydroxy group in component A (alcohol) from 1:0.1 to 1:10.

Embodiment 2

• (Aa) Monoalkohole wie C1- bis C36-Alkanole, ausgewählt aus den Gruppen der nicht-alkoxylierten linearen C2- bis C36-Alkohole, wie Mischungen solcher Alkohole ausgewählt aus C6-bis C22-Fettalkoholen, bevorzugt C8- bis C22-Fettalkoholen, besonders bevorzugt C12- und C14-Fettalkoholen, ganz besonders bevorzugt C16- und C18-Fettalkoholen; nicht alkoxylierte verzweigte C3- bis C36-Alkohole wie 2-Ethylhexanol, 2-Propylheptanol, Isotridecanol, Isononanol, C9-C17-Oxoalkohole; alkoxylierte lineare C2- bis C36-Alkohole wie alkoxylierte Mischungen von C6- bis C22-Fettalkoholen, bevorzugt alkoxylierte Mischungen von C8- bis C22-Fettalkoholen, besonders bevorzugt alkoxylierte Mischungen von C12- und C14-Fettalkoholen, ganz besonders bevorzugt alkoxylierte Mischungen von C16- und C18-Fettalkoholen; alkoxylierte verzweigte C3- bis C36-Alkohole wie alkoxyliertes 2-Ethylhexanol, alkoxyliertes 2-Propylheptanol, alkoxyliertes Isotridecanol, alkoxyliertes Isononanol, alkoxylierte C9-C17-Oxoalkohole;
• (Ab) Dialkohole wie Alkandiole, polyalkoxylierte C2-C6-Alkandiole mit mindestens zwei Hydroxygruppen,
• (Ac) Oligoalkohole wie polyalkoxylierte C3-C6-Alkantriole mit mindestens drei Hydroxygruppen,
• (Ad) Polyole wie Zuckeralkohole, polyalkoxylierte C5-C6-Alkanpolyole, Glycerole wie Diglycerin, Triglycerinpolyglycerin, Dipentaerythrit, Tripentaerythrit; und/oder
• (Ae) Phenoxyalkanole, wie Phenoxyethanol;

wobei die Alkohole, ausgewählt aus den Gruppen der Monoalkohole und alkoxylierten Di-, Oligoalkohole und alkoxylierten Polyole, und die Alkohole, ausgewählt aus der Gruppe(n), Monoalkohole und alkoxylierte Dialkohole, noch stärker bevorzugt sind.Esteramine according to embodiment 1, wherein the alcohol (A) is selected from

• (Aa) monoalcohols such as C1 to C36 alkanols, selected from the groups of non-alkoxylated linear C2 to C36 alcohols, such as mixtures of such alcohols selected from C6 to C22 fatty alcohols, preferably C8 to C22 fatty alcohols, particularly preferably C12 and C14 fatty alcohols, very particularly preferably C16 and C18 fatty alcohols; non-alkoxylated branched C3 to C36 alcohols such as 2-ethylhexanol, 2-propylheptanol, isotridecanol, isononanol, C9-C17 oxo alcohols; alkoxylated linear C2 to C36 alcohols such as alkoxylated mixtures of C6 to C22 fatty alcohols, preferably alkoxylated mixtures of C8 to C22 fatty alcohols, particularly preferably alkoxylated mixtures of C12 and C14 fatty alcohols, very particularly preferably alkoxylated mixtures of C16 and C18 fatty alcohols; alkoxylated branched C3 to C36 alcohols such as alkoxylated 2-ethylhexanol, alkoxylated 2-propylheptanol, alkoxylated isotridecanol, alkoxylated isononanol, alkoxylated C9-C17 oxo alcohols;
• (Ab) dialcohols such as alkanediols, polyalkoxylated C2-C6 alkanediols with at least two hydroxy groups,
• (Ac) Oligoalcohols such as polyalkoxylated C3-C6 alkanetriols with at least three hydroxy groups,
• (Ad) polyols such as sugar alcohols, polyalkoxylated C5-C6 alkane polyols, glycerols such as diglycerol, triglycerolpolyglycerol, dipentaerythritol, tripentaerythritol; and/or
• (Ae) Phenoxyalkanols, such as phenoxyethanol;

the alcohols selected from the groups of monoalcohols and alkoxylated di-, oligoalcohols and alkoxylated polyols, and the alcohols selected from the group(s) of monoalcohols and alkoxylated dialcohols, being even more preferred.

Embodiment 3

• i) Alkylsulfonsäuren, wie Methansulfonsäure, Ethylsulfonsäure, Propylsulfonsäure, Kampfersulfonsäure; Alkylarylsulfonsäuren und insbesondere Alkylbenzolsulfonsäuren, wie Toluolsulfonsäure (einschließlich ihres Isomerengemisches), p-Toluolsulfonsäure, o-Toluolsulfonsäure, m-Toluolsulfonsäure, Xylolsulfonsäure (Isomerengemisch), 2 ,6-Dimethylbenzolsulfonsäure, 2 ,5-Dimethylbenzolsulfonsäure, 2 ,4-Dimethylbenzolsulfonsäure, 4-Dodecylbenzolsulfonsäure, iso-Propylbenzolsulfonsäure, Ethylbenzolsulfonsäure und Naphthalinsulfonsäure,
• ii) anorganische Säuren wie Schwefelsäure, Salzsäure, Bromwasserstoffsäure, Phosphorsäure; vorzugsweise Schwefelsäure;

bevorzugt eine Säure ausgewählt aus Gruppe i), besonders bevorzugt para-Toluolsulfonsäure und Methansulfonsäure, ganz besonders bevorzugt Methansulfonsäure.Esteramine according to embodiment 1 or 2, wherein the acid (D) is selected from

• (i) alkylsulfonic acids, such as methanesulfonic acid, ethylsulfonic acid, propylsulfonic acid, camphorsulfonic acid; alkylarylsulfonic acids and in particular alkylbenzenesulfonic acids, such as toluenesulfonic acid (including its isomer mixture), p-toluenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, xylenesulfonic acid (isomer mixture), 2,6-dimethylbenzenesulfonic acid, 2,5-dimethylbenzenesulfonic acid, 2,4-dimethylbenzenesulfonic acid, 4-dodecylbenzenesulfonic acid, isopropylbenzenesulfonic acid, ethylbenzenesulfonic acid and naphthalenesulfonic acid,
• (ii) inorganic acids such as sulphuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid; preferably sulphuric acid;

preferably an acid selected from group i), particularly preferably para-toluenesulfonic acid and methanesulfonic acid, most preferably methanesulfonic acid.

Embodiment 4

• i) Lacton(e), d. h. cyclische Ester, beginnend mit α-Lacton (drei Ringatome), gefolgt von β-Lacton (vier Ringatome), γ-Lacton (fünf Ringatome) usw.; solche Lactone sind vorzugsweise β-Propiolacton, g-Butyrolacton, δ-Valerolalacton, g-Valerolalacton, e-Caprolacton, d-Decalacton, g-Decalacton, e-Decalacton; vorzugsweise Caprolacton;
• ii) Hydroxysäure(n), die sich von jedem Lacton durch Hydrolyse ableiten lassen, insbesondere von einem beliebigen Lacton innerhalb der Gruppe i) vor, insbesondere eine α-, β- oder γ-Hyd-roxysäure, die von dem entsprechenden Lacton durch Hydrolyse abgeleitet ist, und Milchsäure, Glykolsäure, 4-Hydroxybutansäure, 6-Hydroxyhexansäure, 12-Hydroxystearinsäure, Zitronensäure;

vorzugsweise Milchsäure oder Caprolacton.Esteramine according to one of embodiments 1 to 3, wherein the at least one lactone and/or hydroxy acid (B) is selected from groups i) and/or ii), with

• i) Lactone(s), ie cyclic esters starting with α-lactone (three ring atoms), followed by β-lactone (four ring atoms), γ-lactone (five ring atoms), etc.; such lactones are preferably β-propiolactone, g-butyrolactone, δ-valerolalactone, g-valerolalactone, e-caprolactone, d-decalactone, g-decalactone, e-decalactone; preferably caprolactone;
• (ii) hydroxy acid(s) derivable from any lactone by hydrolysis, in particular from any lactone within group (i), in particular an α-, β- or γ-hydroxy acid derived from the corresponding lactone by hydrolysis, and lactic acid, glycolic acid, 4-hydroxybutanoic acid, 6-hydroxyhexanoic acid, 12-hydroxystearic acid, citric acid;

preferably lactic acid or caprolactone.

Embodiment 5

Esteramine according to any one of embodiments 1 to 4, wherein the lactam or amino acid (C) is selected from lactams which are cyclic amides starting with alpha-lactam (three ring atoms), followed by beta-lactam (four ring atoms), gamma-lactam (five ring atoms) and so on, such as epsilon-caprolactam, gamma-butyrolactam, piparidone, laurolactam; and the corresponding alpha-, beta-, gamma-amino acids etc. which can be obtained from the lactams by hydrolysis; N-methylpyrrolidone; and alpha-amino acids such as alanine, glycine, leucine, isoleucine, valine, proline, phenylalanine, arginine, asparagine, aspartate, glutamine, glutamate, histidine, lysine, threonine, tryptophan, tyrosine, cysteine, methionine, serine; Alpha-amino acids with secondary or tertiary amino groups such as sarcosine, N,N-dimethylglycine; other amino acids such as 6-aminohexanoic acid, 4-aminobutanoic acid, 3-aminopropanoic acid, 12-aminododecanoic acid, 11-aminoundecanoic acid;
Preferably alanine, 6-aminohexanoic acid, 4-aminobutyric acid, particularly preferably epsilon-caprolactam.

Embodiment 6

Esteramine according to any one of embodiments 1 to 5, wherein the esteramine is obtained at least partially as a sulfated esteramine when sulfuric acid is used as acid (D) and at least one alcohol (A) is selected which contains more than one hydroxy group, and is obtained as an at least partially protonated esteramine and a sulfated monoalcohol counterion when a monoalcohol is used as alcohol (A) and sulfuric acid is used as acid (D).

Embodiment 7

Esteramine according to any one of embodiments 1 to 6, wherein the alcohol (A) used is an alkoxylated alcohol obtained by alkoxylating at least one hydroxy group of the alcohol according to embodiment 2 with one or more alkylene oxides to produce alkyleneoxy chains containing one or more units selected from alkylene oxides selected from C2 to C22 alkylene oxides, preferably C2-C4 alkylene oxides, wherein the units originating from the alkylene oxide(s) may be arranged in random, block or multiple block order or combinations thereof, preferably as a block.

Embodiment 8

Esteramine according to any one of embodiments 6 to 7, wherein the acid (D) is selected such that the esteramine is obtained as a salt in zwitterionic or cationic form, preferably the acid selected is methanesulfonic acid and the esteramine obtained is a salt in cationic form, wherein the zwitterionic form additionally requires that at least one alcohol is selected which contains more than one hydroxy group.

Embodiment 9

Esteramine according to one of embodiments 1 to 8, wherein the compounds A, B, C and D are used in a molar ratio OH (of the alcohol component A) : B (lactone/hydroxy acid) : C (lactam/amino acid) : D (acid) which is (1) : (0.1 - 10, preferably 0.1 - 5) : (0.1 - 1) : (0.1 - 1.5).

Embodiment 10

Esteramine according to any one of embodiments 1 to 9, wherein the structure consists of a first alcohol-resulting "block" (X) carrying one or more hydroxy groups, of which at least one hydroxy group is bonded via an ester function to a second block (Y) resulting from a single lactone or an oligo- or polyester block, and a third block (Z) resulting from the addition of an amino acid or a lactam to such a second block, so that the esteramine has the structure "XYZ" or "X(Y)nZ", where n are integers from 1 to 10 when the alcohol (A) is a monoalcohol (from group Aa), while n can be any number from 0.1 to 10 for the esteramine when the alcohol (A) used is selected from groups (Ab), (Ac) and/or (Ad).

Embodiment 11

1. i) mindestens einen Alkohol, der mindestens eine Hydroxygruppe trägt, vorzugsweise mindestens zwei Hydroxygruppen, wobei gegebenenfalls mindestens eine Hydroxygruppe in einem Schritt vor Schritt a) mit mindestens einem Alkylenoxid, bevorzugt mindestens 1 und bis zu 200, bevorzugt 1 bis 100, besonders bevorzugt bis zu 50 Mol Alkylenoxid pro Hydroxygruppe alkoxyliert werden kann,
2. ii) mit mindestens einem Lacton und/oder (bevorzugt oder) Hydroxysäure, besonders bevorzugt nur Lacton, und
3. iii) mit mindestens einem Lactam und/oder (bevorzugt oder) mindestens einer Aminosäure, besonders bevorzugt nur Lactam,
4. iv) in Gegenwart einer anorganischen oder organischen Säure, wobei die organische oder

anorganische Säure vorzugsweise einen pKa-Wert im Bereich von -3 bis +5 aufweist, wobei das molare Verhältnis von Komponente C (Lactam) zu Komponente D (Säure) innerhalb eines Bereichs von 1:0,9 bis 1:1,5, bevorzugt etwa 1:0,95 bis 1:1,1, besonders bevorzugt 1:1 bis 1:1,08 und am meisten bevorzugt etwa 1:1,02 wie genau 1:1,02 liegt.A process for preparing an esteramine according to any one of embodiments 1 to 10, comprising the steps of reacting

1. i) at least one alcohol which carries at least one hydroxyl group, preferably at least two hydroxyl groups, where optionally at least one hydroxyl group can be alkoxylated in a step before step a) with at least one alkylene oxide, preferably at least 1 and up to 200, preferably 1 to 100, particularly preferably up to 50 mol of alkylene oxide per hydroxyl group,
2. ii) with at least one lactone and/or (preferably or) hydroxy acid, particularly preferably only lactone, and
3. iii) with at least one lactam and/or (preferably or) at least one amino acid, particularly preferably only lactam,
4. (iv) in the presence of an inorganic or organic acid, the organic or

inorganic acid preferably has a pKa value in the range of -3 to +5, wherein the molar ratio of component C (lactam) to component D (acid) is within a range of 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1, more preferably 1:1 to 1:1.08 and most preferably about 1:1.02 such as exactly 1:1.02.

Embodiment 12

Process according to embodiment 11, wherein the molar ratio of component C (lactam) to component D (acid) is within a range of 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1, and particularly preferably 1:1 to 1:1.08, and most preferably about 1:1.02, such as exactly 1:1.02, and
Component C (lactam) per hydroxy group in component A (alcohol) at most 1:1, preferably component C less than or equal to per hydroxy group in component A (alcohol), and component B (lactone/hydroxy acid) per hydroxy group in component A (alcohol) from 1:0.1 to 1:10.

Embodiment 13

Process according to embodiment 11 or 12, wherein the compounds A, B, C and D are used in a molar ratio OH (of the alcohol component A) : B (lactone/hydroxy acid) : C (lactam/amino acid) : D (acid) which is (1) : (0.1 - 10, preferably 0.1 - 5) : (0.1 -1) : (0.1 - 1.5).

Embodiment 14

Use of an esteramine or a salt thereof according to any one of embodiments 1 to 10 or obtained by the process according to any one of embodiments 11 to 13 in a composition, i.e. a textile and household care product, a cleaning composition or an industrial and institutional cleaning product.

Embodiment 15

Use according to embodiment 14, wherein the composition comprises at least one esteramine and/or at least one salt thereof in a concentration of about 0.1% to about 5% by weight based on the total weight of such composition or product.

Embodiment 16

Use according to embodiment 14 or 15, wherein the composition is in liquid or semi-liquid form.

Embodiment 17

1. a. mindestens ein Enzym enthaltend,
2. b. enthaltend etwa 1 bis etwa 70 Gew.-% eines Tensidsystems,
3. c. mindestens einen weiteren Reinigungszusatz in wirksamen Mengen enthaltend, und
4. d. die eine verbesserte Waschleistung aufweisen, vorzugsweise in der Primärreinigung.

Use according to any one of embodiments 14 to 16, wherein at least one of the following requirements is further met:

1. a. containing at least one enzyme,
2. b. containing about 1 to about 70% by weight of a surfactant system,
3. c. containing at least one other cleaning additive in effective amounts, and
4. d. which have improved washing performance, preferably in primary cleaning.

Embodiment 18

1. a. mindestens ein Enzym, vorzugsweise ausgewählt aus einer oder mehreren Lipasen, Hydrolasen, Amylasen, Proteasen, Cellulasen, Mannanasen, Hemicellulasen, Phospholipasen, Esterasen, Xylanasen, DNasen, Dispersinen, Pektinasen, Oxidoreduktasen, Cutinasen, Laktasen und Peroxidasen, besonders bevorzugt mindestens zwei der vorgenannten Typen,
2. b. etwa 1 bis etwa 70 Gew.-% eines Tensidsystems,
3. c. mindestens ein weiteres Reinigungshilfsmittel in wirksamen Mengen,

und weist optional eine verbesserte Waschleistung in der Vorreinigung auf.Composition which is a detergent, a cleaning agent or a textile and household care product, containing at least one esteramine and/or a salt thereof according to one of embodiments 1 to 10 or obtained or obtainable by the process according to one of embodiments 11 to 13, comprising the at least one esteramine and/or the at least one salt thereof in a concentration of preferably about 0.1% to about 5% in wt.% based on the total weight of this composition or this product, and optionally further having at least one of the following features: a) to c)

1. a. at least one enzyme, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, mannanases, hemicellulases, phospholipases, esterases, xylana sen, DNases, dispersins, pectinases, oxidoreductases, cutinases, lactases and peroxidases, particularly preferably at least two of the aforementioned types,
2. b. about 1 to about 70% by weight of a surfactant system,
3. c. at least one other cleaning agent in effective quantities,

and optionally has improved washing performance in the pre-cleaning phase.

Embodiment 19

Composition according to embodiment 18, which is in liquid or semi-liquid form, preferably a concentrated liquid detergent formulation, a single-dose detergent formulation, a liquid hand dishwashing detergent formulation or a solid machine dishwashing formulation, particularly preferably a liquid detergent formulation,
optionally further comprising at least one antimicrobial agent, preferably 2-phenoxyethanol, in an amount ranging from 2 ppm to 5%, particularly preferably 0.1 to 2% by weight of the composition, and
optionally 4,4'-dichloro-2-hydroxydiphenyl ether in a concentration of 0.001 to 3%, preferably 0.002 to 1%, particularly preferably 0.01 to 0.6% by weight of the composition.

Embodiment 20

A method of preserving a composition according to any one of embodiments 18 or 19 against microbial contamination or growth, said method comprising adding an antimicrobial agent selected from the group consisting of 2-phenoxyethanol to the composition, which is an aqueous composition containing water as a solvent.

Embodiment 21

A method for washing fabrics or cleaning hard surfaces, the method comprising treating a fabric or hard surface with a composition according to any one of embodiments 18 to 19, wherein the composition comprises 4,4'-dichloro-2-hydroxydiphenyl ether, preferably 4,4'-dichloro-2-hydroxydiphenyl ether in a concentration of 0.001 to 3%, preferably 0.002 to 1%, particularly preferably 0.01 to 0.6%, each by weight of the composition.

Examples

methodology

1H NMR measured in MeOD (deuterated methanol) with the Bruker Avance 400 MHz spectrometer.
The hydroxy values are determined according to DIN53240-1 from 2016. Sample table - examples at a glance Ex. # Example description (components: “A + B + C + D”) 1 2-EH + caprolactone + caprolactam 80% + MSA (1.2 : 3 : 1 : 1.02), 5:1 H2O/caprolactam 2 2-EH + lactic acid + caprolactam 80% + MSA (1.2 : 3 : 1 : 1.02), 5:1 H2O/caprolactam 3 Pluriol E 4000 + 3.0 caprolactone/OH + 1.0 caprolactam/OH + 1.1 MSA/OH 4 Polyglycerin HT + 2 caprolactone/OH + 0.5 caprolactam/OH + 0.51 H2SO4/OH 5 Polyglycerin HT + 2 caprolactone/OH + 1 caprolactam/OH + 1.02 MSA/OH 6 Polyglycerin HT + 2 caprolactone/OH + 0.5 caprolactam/OH + 0.51 MSA/OH 7 Pluriol A 16 TE (= glycerin + 5 EO/OH) + 0.66 caprolactone /OH + 0.66 caprolactam/OH + 0.67 MSA/OH 8th 1 [Trispentaerythritol +20 (EO/OH)] + 3 (caprolactone) + 1 caprolactam + 1.02 MSA 9 Sorbitol + 1 caprolactone/OH + 0.5 caprolactam/OH + 0.51 H2SO4/OH (1 : 6 : 3 : 3.06 mol) 10 Sorbitol + 2 caprolactone/OH + 0.5 caprolactam/OH + 0.51 H2SO4/OH (1 : 12 : 3 : 3.06 mol)

Abbreviations in the example table:

2-EH = 2-ethylhexanol; caprolactone = epsilon-caprolactone; caprolactam = epsilon-caprolactam; MSA = methanesulfonic acid; Pluriol E 4000 = ; polyglycerin HT = ; Pluriol A 16 TE (glycerin + 5 EO/OH) = glycerin, ethoxylated with 5 molar equivalents of ethylene oxide (=EO) per hydroxy group; trispentaerythritol +20 (EO/OH) = trispentaerythritol ethoxylated with 20 molar equivalents of ethylene oxide (=EO) per hydroxy group

Example 1: 2-Ethylhexanol, ester with 3 moles of caprolactone and 1 mole of caprolactam, as methanesulfonic acid salt

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 31.6 g of 2-ethylhexanol, 69.2 g of epsilon-caprolactone and 28.3 g of epsilon-caprolactam (80% aqueous solution) were added. 28.0 g of methanesulfonic acid (70% aqueous solution) was added over 15 minutes. The temperature rose from room temperature to 52°C during the addition. The reaction mixture was heated to reflux and stirred under reflux for 9 hours. The reflux condenser was replaced with a distillation head and the reaction mixture was heated to 125-140°C bath temperature and stirred for 12.5 hours under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled from the reaction mixture. Vacuum was applied and the mixture was stirred for a further 5 hours at 140°C bath temperature and 5 mbar vacuum. 124.8 g of a white solid were obtained. 1H-NMR in MeOD showed 95% conversion to 2-ethylhexanol, ester with 3 moles of caprolactone and 1 mole of caprolactam as methanesulfonic acid salt.

Example 2: 2-Ethylhexanol, ester with 3 moles of lactic acid and 1 mole of caprolactam, as methanesulfonic acid salt

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 39.5 g of 2-ethylhexanol, 75.0 g of lactic acid (90% in water) and 35.4 g of epsilon-caprolactam (80% aqueous solution) were added. 35.0 g of methanesulfonic acid (70% aqueous solution) was added over 15 minutes. The temperature rose from room temperature to 33°C during the addition. The reaction mixture was heated to reflux and stirred under reflux for 4 hours. The reflux condenser was replaced with a distillation head and the reaction mixture was heated to 125-140°C bath temperature and stirred for 11 hours under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled from the reaction mixture. Vacuum was applied and the mixture was stirred for a further 15 hours at 140°C bath temperature and 5 mbar vacuum. 119.0 g of a white solid were obtained. 1H-NMR in MeOD showed complete conversion to 2-ethylhexanol, ester with 3 moles of lactic acid and 1 mole of caprolactam as methanesulfonic acid salt.

Example 3: Polyethylene glycol, molecular weight 4000 g/mol, ester with 6 moles caprolactone and 2 moles caprolactam, as methanesulfonic acid salt

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 123.1 g of polyethylene glycol, molecular weight 4000 g/mol (Pluriol® E 4000), 20.5 g of epsilon-caprolactone and 6.8 g of epsilon-caprolactam were heated to 120 °C bath temperature. 6.3 g of methanesulfonic acid were added over 5 minutes. The reflux condenser was replaced by a distillation head and the reaction mixture was stirred for 9.5 hours at 120 °C bath temperature under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled off from the reaction mixture. The bath temperature was increased to 140 °C and the mixture was stirred for an additional 6 hours. 145.0 g of a white solid was obtained. 1H NMR in MeOD showed complete conversion to polyethylene glycol, molecular weight 4000 g/mol, ester with 6 mol caprolactone and 2 mol caprolactam as methanesulfonic acid salt.

Example 4: Polyglycerol, ester with 2 moles of caprolactone per hydroxy group and 0.5 moles of caprolactam per hydroxy group, sulfated with 0.5 moles of sulfuric acid per hydroxy group

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 24.4 g of polyglycerol (hydroxy number 1148 mgKOH/g), 115.3 g of epsilon-caprolactone and 35.4 g of epsilon-caprolactam (80% aqueous solution) were added. 26.1 g of sulfuric acid (96%) were added within 15 minutes. The temperature was increased from room temperature to 40°C during the addition. The reaction mixture was heated to reflux and stirred under reflux for 22 hours. The reflux condenser was replaced with a distillation head and the reaction mixture was heated to 125-140°C bath temperature and stirred for 12.5 hours under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled from the reaction mixture. Vacuum was applied and the mixture was stirred for an additional 12 hours at 140°C bath temperature and 5 mbar vacuum. 185.0 g of a brown solid was obtained. 1H NMR in MeOD showed complete conversion to polyglycerol, ester with 2 moles of caprolactone per hydroxy group and 0.5 moles of caprolactam per hydroxy group, sulfated with 0.5 moles of sulfuric acid per hydroxy group.

Example 5: Polyglycerol, ester with 2 moles of caprolactone per hydroxy group and 1 mole of caprolactam per hydroxy group, as methanesulfonic acid salt

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 17.1 g of polyglycerol (hydroxy number 1148 mgKOH/g), 80.7 g of epsilon-caprolactone and 49.5 g of epsilon-caprolactam (80% aqueous solution) were added. 49.0 g of methanesulfonic acid (70% aqueous solution) was added over 5 minutes. The temperature rose from room temperature to 30°C during the addition. The reaction mixture was heated to reflux and stirred under reflux for 5 hours. The reflux condenser was replaced with a distillation head and the reaction mixture was heated to 125-140°C bath temperature and stirred for 12 hours under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled from the reaction mixture. Vacuum was applied and the mixture was stirred for a further 12 hours at 140°C bath temperature and 5 mbar vacuum. 150.0 g of a beige solid were obtained. 1H-NMR in MeOD showed complete conversion to polyglycerol, ester with 2 moles of caprolactone per hydroxy group and 1 mole of caprolactam per hydroxy group, as methanesulfonic acid salt

Example 6: Polyglycerol, ester with 2 moles of caprolactone per hydroxy group and 0.5 moles of caprolactam per hydroxy group, as methanesulfonic acid salt

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 21.9 g of polyglycerol (hydroxy number 1148 mgKOH/g), 103.8 g of epsilon-caprolactone and 31.8 g of epsilon-caprolactam (80% aqueous solution) were added. 31.5 g of methanesulfonic acid (70% aqueous solution) was added over 5 minutes. The temperature rose from room temperature to 30°C during the addition. The reaction mixture was heated to reflux and stirred under reflux for 5 hours. The reflux condenser was replaced with a distillation head and the reaction mixture was heated to 125-140°C bath temperature and stirred for 17 hours under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled from the reaction mixture. Vacuum was applied and the mixture was stirred for a further 12 hours at 140°C bath temperature and 5 mbar vacuum. 151.0 g of a beige solid were obtained. 1H-NMR in MeOD showed complete conversion to polyglycerol, ester with 2 moles of caprolactone per hydroxy group and 0.5 moles of caprolactam per hydroxy group, as methanesulfonic acid salt

Example 7: Glycerol ethoxylate, molecular weight 750 g/mol, ester with 2 moles of caprolactone and 2 moles of caprolactam, as methanesulfonic acid salt

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 154.3 g of glycerol ethoxylate, molecular weight 750 g/mol, 50.2 g of epsilon-caprolactone and 49.8 g of epsilon-caprolactam were heated to 120 °C bath temperature. 42.5 g of methanesulfonic acid were added over 5 minutes. The reflux condenser was replaced by a distillation head and the reaction mixture was stirred for 9 hours at 135 °C bath temperature under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled off from the reaction mixture. Vacuum was applied and the mixture was stirred for a further 15 hours at 140 °C bath temperature and 5 mbar vacuum. 290.0 g of a brown solid was obtained. 1H NMR in MeOD gave 96% conversion to glycerol ethoxylate, molecular weight 750 g/mol, ester with 2 moles of caprolactone and 2 moles of caprolactam as methanesulfonic acid salt.

Example 8: Trispentaerythritol, ethoxylated with 160 moles of ethylene oxide, ester with 24 moles of caprolactone and 8 moles of caprolactam, as methanesulfonic acid salt

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 200.0 g of trispentaerythritol ethoxylated with 160 moles of ethylene oxide, 74.0 g of epsilon-caprolactone, 30.6 g of epsilon-caprolactam (80% aqueous solution) and 13.1 g of water were added. 21.7 g of methanesulfonic acid was added over 5 minutes. The temperature rose from room temperature to 45°C during the addition. The reaction mixture was heated to reflux and stirred under reflux for 3 h. The reflux condenser was replaced with a distillation head and the reaction mixture was stirred for 6 h at 135°C bath temperature under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled off from the reaction mixture. 310.0 g of a brown solid was obtained. 1H-NMR in MeOD gave 97% conversion to trispentaerythritol ethoxylated with 160 mol ethylene oxide, ester with 24 mol caprolactone and 8 mol caprolactam as methanesulfonic acid salt

Example 9: Sorbitol, ester with 6 moles of caprolactone and 3 moles of caprolactam, sulfated with 3 moles of sulfuric acid

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 36.4 g of sorbitol, 137.0 g of epsilon-caprolactone, 84.9 g of epsilon-caprolactam (80% aqueous solution) and 34.6 g of water were added. 62.5 g of sulfuric acid (96%) was added over 5 minutes. The temperature was raised from room temperature to 40°C during the addition. The reaction mixture was heated to reflux and stirred under reflux for 3 hours. The reflux condenser was replaced with a distillation head and the reaction mixture was heated to 125-140°C bath temperature and stirred for 5 hours under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled from the reaction mixture. Vacuum was applied and the mixture was stirred for an additional 5 hours at 140°C bath temperature and 750 mbar vacuum. 270.0 g of a beige solid was obtained. 1H NMR in MeOD gave 97% conversion to sorbitol, ester with 6 mol caprolactone and 3 mol caprolactam, sulfated with 3 mol sulfuric acid.

Example 10: Sorbitol, ester with 12 moles of caprolactone and 3 moles of caprolactam, sulfated with 3 moles of sulfuric acid

In a 4-neck vessel equipped with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 36.4 g of sorbitol, 273.9 g of epsilon-caprolactone, 84.9 g of epsilon-caprolactam (80% aqueous solution) and 34.6 g of water were added. 62.5 g of sulfuric acid (96%) was added over 5 minutes. The temperature was raised from room temperature to 40°C during the addition. The reaction mixture was heated to reflux and stirred under reflux for 3 hours. The reflux condenser was replaced with a distillation head and the reaction mixture was heated to 125-140°C bath temperature and stirred for 2 hours under a constant stream of nitrogen bubbling through the reaction mixture. Water was distilled from the reaction mixture. Vacuum was applied and the mixture was stirred for a further 5 hours at 140°C bath temperature and 750 mbar vacuum. 430.0 g of a beige solid was obtained. 1H-NMR in MeOD gave 99% conversion to sorbitol, ester with 12 mol caprolactone and 3 mol caprolactam, sulfated with 3 mol sulfuric acid.

QUOTES INCLUDED IN THE DESCRIPTION

This list of documents listed by the applicant was generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA accepts no liability for any errors or omissions.

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Claims (11)

Esteramine and its salt, obtainable by a process which comprises the step of reacting A + B + C in the presence of D with i) at least one alcohol which carries at least one hydroxy group, where optionally at least one hydroxy group can be alkoxylated in a step before step a) with at least one alkylene oxide, preferably at least 1 and up to 200, preferably 1 to 100, particularly preferably up to 50 mol of alkylene oxide per hydroxy group, ii) at least one lactone and/or (preferably or) hydroxy acid, particularly preferably only lactone, iii) with at least one lactam and/or (preferably or) at least one amino acid, particularly preferably only lactam, and iv) an inorganic or organic acid, where the organic or inorganic acid preferably has a pKa value in the range from -3 to +5, particularly preferably from -2.5 to 1.5, preferably organic acid, particularly preferably sulfonic acids, even more preferably alkanesulfonic acid and/or arylsulfonic acid, particularly preferably Alkanesulfonic acid, very particularly preferably methanesulfonic acid, wherein the molar ratio of component C (lactam) to component D (acid) is in a range from 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1 and particularly preferably 1:1 to 1:1.08 and very particularly preferably about 1:1.02 such as exactly 1:1.02, and component C (lactam) per hydroxy group in component A (alcohol) at most 1:1, preferably component C less than or equal to per hydroxy group in component A (alcohol), and component B (lactone/hydroxy acid) per hydroxy group in component A (alcohol) from 1:0.1 to 1:10, and wherein preferably the acid (D) is selected from i) alkylsulfonic acids, such as methanesulfonic acid, ethylsulfonic acid, propylsulfonic acid, camphorsulfonic acid; Alkylarylsulfonic acids and in particular alkylbenzenesulfonic acids, such as toluenesulfonic acid (including its isomer mixture), p-toluenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, xylenesulfonic acid (isomer mixture), 2,6-dimethylbenzenesulfonic acid, 2,5-dimethylbenzenesulfonic acid, 2,4-dimethylbenzenesulfonic acid, 4-dodecylbenzenesulfonic acid, isopropylbenzenesulfonic acid, ethylbenzenesulfonic acid and naphthalenesulfonic acid, ii) inorganic acids such as sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid; preferably sulfuric acid; particularly preferably an acid selected from group i), particularly preferably para-toluenesulfonic acid and methanesulfonic acid, very particularly preferably methanesulfonic acid; and/or wherein preferably the lactam or amino acid (C) is selected from lactams which are cyclic amides starting with alpha-lactam (three ring atoms), followed by beta-lactam (four ring atoms), gamma-lactam (five ring atoms) and so on, such as epsilon-caprolactam, gamma-butyrolactam, piparidone, laurolactam; and the corresponding alpha-, beta-, gamma-amino acids etc. which can be obtained from the lactams by hydrolysis; N-methylpyrrolidone; and alpha-amino acids such as alanine, glycine, leucine, isoleucine, valine, proline, phenylalanine, arginine, asparagine, aspartate, glutamine, glutamate, histidine, lysine, threonine, tryptophan, tyrosine, cysteine, methionine, serine; Alpha-amino acids with secondary or tertiary amino groups such as sarcosine, N,N-dimethylglycine; other amino acids such as 6-aminohexanoic acid, 4-aminobutanoic acid, 3-aminopropanoic acid, 12-aminododecanoic acid, 11-aminoundecanoic acid; preferably alanine, 6-aminohexanoic acid, 4-aminobutyric acid, particularly preferably epsilon-caprolactam; and/or wherein preferably the alcohol (A) used is an alkoxylated alcohol which is obtained by alkoxylation of at least one hydroxy group of the alcohol according to Claim 2 with one or more alkylene oxides to produce alkyleneoxy chains containing one or more units selected from alkylene oxides selected from C2 to C22 alkylene oxides, preferably C2-C4 alkylene oxides, wherein the units originating from the alkylene oxide(s) may be arranged in random, block or multi-block order or combinations thereof, preferably as a block; and/or wherein preferably the esteramine is obtained at least partially as a sulfated esteramine when sulfuric acid is used as acid (D) and at least one alcohol (A) is selected which contains more than one hydroxy group, and is obtained as an at least partially protonated esteramine and a sulfated monoalcohol counterion when a monoalcohol is used as alcohol (A) and sulfuric acid is used as acid (D). Esteramine after Claim 1 , wherein the alcohol (A) is selected from (Aa) monoalcohols such as C1 to C36 alkanols, selected from the groups of non-alkoxylated linear C2 to C36 alcohols, such as mixtures of such alcohols selected from C6 to C22 fatty alcohols preferably C8 to C22 fatty alcohols, particularly preferably C12 and C14 fatty alcohols, very particularly preferably C16 and C18 fatty alcohols; non-alkoxylated branched C3 to C36 alcohols such as 2-ethylhexanol, 2-propylheptanol, isotridecanol, isononanol, C9-C17 oxo alcohols; alkoxylated linear C2 to C36 alcohols such as alkoxylated mixtures of C6 to C22 fatty alcohols, preferably alkoxylated mixtures of C8 to C22 fatty alcohols, particularly preferably alkoxylated mixtures of C12 and C14 fatty alcohols, very particularly preferably alkoxylated mixtures of C16 and C18 fatty alcohols; alkoxylated branched C3 to C36 alcohols such as alkoxylated 2-ethylhexanol, alkoxylated 2-propylheptanol, alkoxylated isotridecanol, alkoxylated isononanol, alkoxylated C9-C17 oxo alcohols; (Ab) dialcohols such as alkanediols, polyalkoxylated C2-C6 alkanediols with at least two hydroxy groups, (Ac) oligoalcohols such as polyalkoxylated C3-C6 alkanetriols with at least three hydroxy groups, (Ad) polyols such as sugar alcohols, polyalkoxylated C5-C6 alkanepolyols, glycerols such as diglycerol, triglycerolpolyglycerol, dipentaerythritol, tripentaerythritol; and/or (Ae) phenoxyalkanols such as phenoxyethanol; the alcohols selected from the groups of monoalcohols and alkoxylated di-, oligoalcohols and alkoxylated polyols, and the alcohols selected from the group(s) of monoalcohols and alkoxylated dialcohols, being even more preferred. Esteramine according to one of the Claims 1 until 2 , wherein the at least one lactone and/or hydroxy acid (B) is selected from groups i) and/or ii), with i) lactone(s), ie cyclic esters starting with α-lactone (three ring atoms), followed by β-lactone (four ring atoms), γ-lactone (five ring atoms), etc.; such lactones are preferably β-propiolactone, g-butyrolactone, δ-valerolalactone, g-valerolalactone, e-caprolactone, d-decalactone, g-decalactone, e-decalactone; preferably caprolactone; ii) hydroxy acid(s) derivable from any lactone by hydrolysis, in particular from any lactone within group i), in particular an α-, β- or γ-hydroxy acid derived from the corresponding lactone by hydrolysis, and lactic acid, glycolic acid, 4-hydroxybutanoic acid, 6-hydroxyhexanoic acid, 12-hydroxystearic acid, citric acid; preferably lactic acid or caprolactone. Esteramine according to one of the Claims 1 until 3 , wherein the acid (D) is chosen so that the esteramine is obtained as a salt in zwitterionic or cationic form, preferably the acid chosen is methanesulfonic acid and the esteramine obtained is a salt in cationic form, wherein the zwitterionic form additionally requires that at least one alcohol is selected which contains more than one hydroxy group. Esteramine according to one of the Claims 1 until 4 , wherein the compounds A, B, C and D are used in a molar ratio OH (of the alcohol component A) : B (lactone/hydroxy acid) : C (lactam/amino acid) : D (acid) which is (1) : (0.1 - 10, preferably 0.1 - 5) : (0.1 - 1) : (0.1 - 1.5). Esteramine according to one of the Claims 1 until 5 , the structure consisting of a first "block" (X) resulting from alcohol carrying one or more hydroxy groups, at least one of which hydroxy group is linked via an ester function to a second block (Y) resulting from a single lactone or an oligo- or polyester block, and a third block (Z) resulting from the addition of an amino acid or a lactam to such a second block, so that the esteramine has the structure "XYZ" or "X(Y)nZ", where n are integers from 1 to 10 when the alcohol (A) is a monoalcohol (from group Aa), while n can be any number from 0.1 to 10 for the esteramine when the alcohol (A) used is selected from groups (Ab), (Ac) and/or (Ad). Process for preparing an esteramine according to one of the Claims 1 until 6 , comprising the steps of reacting i) at least one alcohol which carries at least one hydroxyl group, preferably at least two hydroxyl groups, where optionally at least one hydroxyl group can be alkoxylated in a step before step a) with at least one alkylene oxide, preferably at least 1 and up to 200, preferably 1 to 100, particularly preferably up to 50 mol of alkylene oxide per hydroxyl group, ii) with at least one lactone and/or (preferably or) hydroxy acid, particularly preferably only lactone, and iii) with at least one lactam and/or (preferably or) at least one amino acid, particularly preferably only lactam, iv) in the presence of an inorganic or organic acid, where the organic or inorganic Acid preferably has a pKa value in the range of -3 to +5, wherein the molar ratio of component C (lactam) to component D (acid) is within a range of 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1, particularly preferably 1:1 to 1:1.08 and most preferably about 1:1.02, such as exactly 1:1.02, wherein preferably the molar ratio of component C (lactam) to component D (acid) is within a range of 1:0.9 to 1:1.5, preferably about 1:0.95 to 1:1.1 and particularly preferably 1:1 to 1:1.08 and most preferably about 1:1.02, such as exactly 1:1.02, and component C (lactam) per hydroxy group in component A (alcohol) is at most 1:1, preferably component C is less than equal to per Hydroxy group in component A (alcohol), and component B (lactone/hydroxy acid) per hydroxy group in component A (alcohol) of 1:0.1 to 1:10, wherein in particular the compounds A, B, C and D are used in a molar ratio OH (of the alcohol component A) : B (lactone/hydroxy acid) : C (lactam/amino acid) : D (acid) which is (1) : (0.1 - 10, preferably 0.1 - 5) : (0.1 - 1) : (0.1 - 1.5). Use of an esteramine or a salt thereof according to any one of the Claims 1 until 6 or obtained by the procedure according to Claim 7 in a composition, ie a textile and household care product, a cleaning composition or an industrial and institutional cleaning product, wherein preferably i) the composition comprises at least one esteramine and/or at least one salt thereof in a concentration of about 0.1% to about 5% by weight based on the total weight of such composition or product, and/or ii) the composition is in liquid or semi-liquid form; and/or iii) additionally at least one of the following requirements is met: a. containing at least one enzyme, b. containing about 1 to about 70% by weight of a surfactant system, c. containing at least one further cleaning additive in effective amounts, and d. which have improved washing performance, preferably in primary cleaning. Composition which is a detergent, a cleaning agent or a textile and household care product containing at least one esteramine and/or a salt thereof according to one of the Claims 1 until 6 or by the procedure according to Claim 7 obtained or obtainable, comprising the at least one esteramine and/or the at least one salt thereof in a concentration of preferably about 0.1% to about 5% in wt. %, based on the total weight of this composition or this product, and optionally further having at least one of the following features: a) to c) a. at least one enzyme, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, mannanases, hemicellulases, phospholipases, esterases, xylanases, DNases, dispersins, pectinases, oxidoreductases, cutinases, lactases and peroxidases, particularly preferably at least two of the aforementioned types, b. about 1 to about 70 wt.% of a surfactant system, c. at least one further cleaning aid in effective amounts, and optionally has improved washing performance in the pre-cleaning phase; wherein preferably the composition is in liquid or semi-liquid form, preferably a concentrated liquid detergent formulation, a single-dose detergent formulation, a liquid hand dishwashing detergent formulation or a solid machine dishwashing formulation, particularly preferably a liquid detergent formulation, optionally further containing at least one antimicrobial agent, preferably 2-phenoxyethanol, in an amount in the range of 2 ppm to 5%, particularly preferably 0.1 to 2% by weight of the composition, and/or optionally 4,4'-dichloro-2-hydroxydiphenyl ether in a concentration of 0.001 to 3%, preferably 0.002 to 1%, particularly preferably 0.01 to 0.6% by weight of the composition. A method for preserving a composition according to any one of Claims 8 or 9 against microbial contamination or growth, which method comprises adding an antimicrobial agent selected from the group consisting of 2-phenoxyethanol to the composition which is an aqueous composition containing water as a solvent. A method for washing fabrics or cleaning hard surfaces, the method comprising treating a fabric or hard surface with a composition according to any one of Claims 8 or 9 wherein the composition comprises 4,4'-dichloro-2-hydroxydiphenyl ether, preferably 4,4'-dichloro-2-hydroxydiphenyl ether in a concentration of 0.001 to 3%, preferably 0.002 to 1%, particularly preferably 0.01 to 0.6%, each by weight of the composition.