EP1042055A1

EP1042055A1 - Use of cyclic carbonates

Info

Publication number: EP1042055A1
Application number: EP98965795A
Authority: EP
Inventors: Jörg KAHRE; Thorsten LÖHL; Holger Tesmann; Hermann Hensen
Original assignee: Cognis Deutschland GmbH and Co KG
Current assignee: BASF Personal Care and Nutrition GmbH
Priority date: 1997-12-18
Filing date: 1998-12-09
Publication date: 2000-10-11
Also published as: WO1999032216A1; DE19756454C1; JP2001526106A

Abstract

The invention relates to the use of cyclic carbonates of formula (I), wherein R?1 and R2¿ represent independently of each other hydrogen or optionally hydroxy-substituted alkyl radicals with 1-10 carbon atoms, as emulsifiers in the production of surface-active preparations. The cyclic carbonates enable active substances, which are otherwise hard to emulsify, to be incorporated into cosmetic agents and also possess reviving properties.

Description

Use of cyclic carbonates

Field of the Invention

The invention relates to the use of cyclic carbonates as emulsifiers, substitutes for silicone oils and softeners.

State of the art

A large number of compounds are known from the prior art which have emulsifying properties; Nonionic surfactants such as e.g. Fatty alcohol polyglycol ethers too. However, in the course of stricter economic requirements for "intelligent" cosmetic raw materials, there is a need for substances that not only have emulsifying properties, but can also take on further tasks in the final formulation. The aim is to reduce the number of individual components in order to reduce the Preparing preparations with reduced technical effort and at lower costs There is particular interest in emulsifiers which allow active ingredients which are otherwise difficult to emulsify, such as the anti-dandruff climbazoi, to be stably incorporated into formulations and at the same time replace or replace silicone oils in cosmetic preparations can at least partially replace, ie have sufficient anti-static and anti-static properties. The object of the present invention was to provide such “multi-function compounds”.

Description of the invention

The invention relates to the use of cyclic carbonates of the formula (I),

in which R ¹ and R ² independently of one another represent hydrogen or optionally hydroxy-substituted alkyl radicals having 1 to 30, preferably 6 to 10, carbon atoms, as emulsifiers for the preparation of surface-active preparations, such as, for example, cosmetic agents, detergents, dishwashing detergents, finishing agents and Varnishes and paints.

Surprisingly, it was found that cyclic carbonates have excellent emulsifying properties and in particular also allow active ingredients which are otherwise difficult to emulsify to be incorporated stably and without turbidity into formulations. Another advantage is that cyclic carbonates are multifunctional compounds, i.e. apart from their emulsifying properties, they are still of particular interest for the production of cosmetic preparations, since they unexpectedly improve the combability of dry hair, which is particularly important for long hair, and even outperform the silicone oils known for this purpose on the market.

Cyclic carbonates

Cyclic carbonates are produced by transesterification of dimethyl carbonate or diethyl carbonate with glycerol or vicinal diols, preferably 1, 2-diols. Typical examples of suitable cyclic carbonates are the transesterification products of the lower dialkyl carbonates mentioned with ethylene glycol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-octanediol, 1, 2-decanediol, 1, 2-dodecanediol and 1, 2- Hexadecanediol. The diols mentioned are generally prepared by opening the corresponding terminal olefin epoxides with water; analog, of course, 1, 2-diols can also serve as starting materials, which are obtained on the basis of internal olefin epoxides. From an application point of view, the use of glycerol carbonate is preferred. The proportion of cyclic carbonates in the surface-active agents can be 0.01 to 50, preferably 0.1 to 30 and in particular 5 to 10% by weight.

Surfactants

The cyclic carbonates can be used in the surface-active agents together with anionic, nonionic, cationic and amphoteric or zwitterionic surfactants. Typical examples of anionic surfactants are soaps, alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, mono-ether sulfate sulfates (hydroxymethoglysulfate), Mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acylamino acids, such as acyllactyl acids latex, acyl tartrates, acyl glutamates and acyl aspartates, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially vegetable products based on wheat) and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution. Typical examples of non-ionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, optionally partially oxidized alk (en) yl oligoglycosides or glucorucyl amide derivatives (especially glucoronic acid amide), in particular glucorucyl amide derivatives (especially glucoronic acid amide) Wheat-based products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution. Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts. Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, reference is made to relevant reviews, for example J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), "Catalysts, Surfactants and mineral oil additives ", Thieme Verlag, Stuttgart, 1978, pp. 123-217. The cyclic carbonates are preferably used together with alkyl ether sulfates and / or alkyl and / or alkenyl oligoglycosides. The weight ratio of the cyclic carbonates to the surfactants can be 99: 1 to 1:99, in particular 90:10 to 10:90, preferably 75:25 to 25:75 and particularly preferably 60:40 to 40:60. The proportion of surfactants in the compositions can be in the range from 1 to 50, preferably 5 to 30 and in particular 15 to 25% by weight.

Oil body

The cyclic carbonates can be used together with oil bodies for the production of surface-active agents, especially cosmetic preparations. Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C22 fatty acids with linear C6-C22 fatty alcohols, esters of branched Cβ-C 1 - carboxylic acids with linear C6-C22 come as oil bodies, for example -Fatty alcohols, esters of linear C6-C22 fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of linear and / or branched fatty acids with polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based Cδ-Cio fatty acids, liquid mono- / di- / triglyceride mixtures based on C6-Ci8 fatty acids, esters of C6-C ₂ 2 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, especially benzoic acid, esters of C2-Ci2-dicarboxylic acids with linear or branched alcohols with 1 to 22 carbon atoms or polyols with 2 to 10 carbon atoms and 2 up to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear C6-C22 fatty alcohol carbonates, Guerbet carbonates, esters of benzoic acid with linear and / or branched C6-C22 alcohols (e.g. Finsolv® TN), dialkyl ethers, ring opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic hydrocarbons. The proportion of the oil bodies in the surface-active agents can be 5 to 85, preferably 10 to 70 and in particular 15 to 50% by weight.

Co-emulsifiers

The cyclic carbonates can be used together with co-emulsifiers. For example, nonionic surfactants from at least one of the following groups can be used:

(a1) Adducts of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 carbon atoms, with fatty acids with 12 to 22 carbon atoms and with alkylphenols with 8 to 15 carbon atoms in the Alkyl group;

(a2) Ci2 / i8 fatty acid monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol;

(a3) glycerol monoesters and diesters and sorbitan monoesters and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and their ethylene oxide addition products;

(a4) alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs;

(a5) adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil;

(a6) polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate. Mixtures of compounds from several of these classes of substances are also suitable;

(a7) adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil;

(a8) partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, butyl glucoside, butyl glucoside - glucoside) and polyglucosides (eg cellulose);

(a9) mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates;

(a10) wool wax alcohols;

(a11) polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives;

(a12) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE-PS 1165574 and / or mixed esters of fatty acids with 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol and

(a13) polyalkylene glycols. The adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are homolog mixtures, the middle of which Degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out. Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.

Cβ / 18 alkyl mono- and oligoglycosides, their preparation and their use are known from the prior art. They are produced in particular by reacting giucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms. Regarding the glycoside residue, both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to about 8 are suitable. The degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.

Zwitterionic surfactants can also be used as emulsifiers. Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate. The fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred. Suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a Cβ-alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / i8-acylsarcosine. In addition to the ampholytic emulsifiers, quaternary emulsifiers are also suitable, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred. The share of co- Emulsifiers on the surface-active agents can be 1 to 25, preferably 3 to 15 and in particular 5 to 10% by weight.

Active ingredients

A particular advantage of the cyclic carbonates to be used according to the invention is that they can be used to incorporate active ingredients which are otherwise very difficult to emulsify stably and without turbidity into formulations. Suitable biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudo-ceramides, essential oils, plant extracts and vitamin complexes. Octopirox and zinc pyrethione and in particular climbazole can be used as antidandruff agents. The proportion of the active ingredients in the surface-active agents can be 0.1 to 5, preferably 0.5 to 3 and in particular 1 to 2% by weight.

Pearlescent waxes

The cyclic carbonates are also particularly suitable as emulsifiers for pearlescent waxes, in particular together with alkyl glucosides and silicone oils. Pearlescent waxes, for example, are: alkylene glycol esters; Fatty acid alkanolamides; Partial glycerides; Esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms; Fatty acids; Ring opening products of olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof.

• alkylene glycol ester. The alkylene glycol esters are usually mono- and / or diesters of alkylene glycols which follow the formula (II)

R ³ CO (OA) _n OR4 (II)

in which R ³ CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, R ^{4 is} hydrogen or R ³ CO and A is a linear or branched alkylene radical having 2 to 4 carbon atoms and n is a number from 1 to 5 stands. Typical examples are mono- and / or diesters of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, Triethylene glycol or tetraethylene glycol with fatty acids with 6 to 22, preferably 12 to 18 carbon atoms as there are: caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid , Linoleic acid, linolenic acid, elaeostearic acid, arachinic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures. The use of ethylene glycol mono- and / or distearate is particularly preferred.

• fatty acid alkanolamides. Fatty acid alkanolamides which can be used as pearlescent waxes follow the formula (III),

in the R ⁵ CO for a linear or branched, saturated or unsaturated acyl radical with 6 to 22 carbon atoms, R ⁶ for hydrogen or an optionally hydroxy-substituted alkyl radical with 1 to 4 carbon atoms and B for a linear or branched alkylene group with 1 to 4 carbon atoms stands. Typical examples are condensation products of ethanoiamine, methylethanolamine, diethanolamine, propanolamine, methyropropanolamine and dipropanolamine as well as their mixtures with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, oleic acid, stearic acid, stearic acid, stearic acid Petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures. The use of stearic acid ethanolamide is particularly preferred.

• partial glycerides. Partial glycerides which have pearlescent properties are mono- and / or diesters of glycerol with fatty acids, namely, for example, caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, elaidic acid , Linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures. They follow the formula (IV),

in which R ⁷ CO for a linear or branched acyl radical having 6 to 22 carbon atoms, R ⁸ and R ⁹ independently of one another for hydrogen or R ⁷ CO, x, y and z in total for 0 or for numbers from 1 to 30 and X for is an alkali or alkaline earth metal with the proviso that at least one of the R ⁸ and R ^{9 represent} hydrogen. Typical examples are lauric acid, lauric, coconut fatty, coconut fatty acid triglyceride, glyceride palmitic acid, Palmitinsäuretriglycerid, oleic, stearic acid diglyceride, isostearic acid monoglyceride, Isostearinsäurediglycerid, oleic acid diglyceride, monoglyceride monoglyceride tallow, Talgfettsäurediglycerid, behenic acid, Behensäurediglycerid, erucic casäuremonoglycerid, Erucasäuredigiycerid and technical mixtures which may still contain small amounts of triglyceride from the manufacturing process.

Polyvalent carboxylic and hydroxycarboxylic esters. Pearlescent waxes are further esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms. Examples of suitable acid components of these esters are malonic acid, maleic acid, fumaric acid, adipic acid, sebacic acid, azelaic acid, dodecanedioic acid, phthalic acid, isophthalic acid and in particular succinic acid and malic acid, citric acid and in particular tartaric acid and mixtures thereof. The fatty alcohols contain 6 to 22, preferably 12 to 18 and in particular 16 to 18 carbon atoms in the alkyl chain. Typical examples are capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capricinal alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linoleyl alcohol alcohol , Erucyl alcohol and brassidyl alcohol and their technical mixtures. The esters can be present as full or partial esters, preferably mono- and especially diesters of carboxylic or hydroxycarboxylic acids. Typical examples are succinic acid mono- and -dilauryl esters, succinic acid mono- and -dicetearly esters, succinic acid mono- and -distearyl esters, tartaric acid mono- and -dilauryl esters, tartaric acid mono- and dicocoalkyl esters, tartaric acid mono- and -dicetearyl esters, citric acid and mono- trilaury esters, citric acid mono-, di- and tricocoalkyl esters as well as citric acid mono-, di- and tricetearyl esters.

Fatty alcohols. Long-chain fatty alcohols which follow the formula (V) can be used as a further group of pearlescent waxes,

R ° OH (V)

in which R ^{10 represents} a linear alkyl radical having 24 to 48, preferably 32 to 36, carbon atoms. The substances mentioned are usually oxidation products of long-chain paraffins.

Fat ketones. Fat ketones which are suitable as component (a) preferably follow the formula (VI), RH-CO-R ¹ * (VI)

in which R ¹¹ and R ¹² independently of one another represent alkyl and / or alkenyl radicals having 1 to 22 carbon atoms, with the proviso that they have a total of at least 24 and preferably 32 to 48 carbon atoms. The ketones can be prepared by methods known in the art, for example by pyrolysis of the corresponding fatty acid magnesium salts. The ketones can be symmetrical or asymmetrical, but the two radicals R ¹¹ and R ¹² preferably differ only by one carbon atom and are derived from fatty acids having 16 to 22 carbon atoms. Stearon is characterized by particularly advantageous pearlescent properties.

Fatty aldehydes. Fatty aldehydes suitable as pearlescent waxes correspond to the formula (VII)

R «COH (VII)

in which R ¹³ CO represents a linear or branched acyl radical having 24 to 48, preferably 28 to 32, carbon atoms.

Fatty ether. Also suitable as pearlescent waxes are fatty ethers of the formula (VIII)

in which R ¹⁴ and R ¹⁵ independently of one another represent alkyl and / or alkenyl radicals having 1 to 22 carbon atoms, with the proviso that they have a total of at least 24 and preferably 32 to 48 carbon atoms. Fat ethers of the type mentioned are usually prepared by acidic condensation of the corresponding fatty alcohols. Fat ethers with particularly advantageous pearlescent properties are obtained by condensation of fatty alcohols having 16 to 22 carbon atoms, such as, for example, cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol and / or erucyl alcohol.

Fatty carbonates. Fatty carbonates of the formula (IX) are also suitable as component (a)

R ¹⁶ 0-C0-0R17 (IX)

in which R ¹⁶ and R ¹⁷ independently of one another represent alkyl and / or alkenyl radicals having 1 to 22 carbon atoms, with the proviso that they have a total of at least 24 and preferably 32 to 48 carbon atoms. The substances are obtained by, for example, dimethyl or Transesterified with the appropriate fatty alcohols in a manner known per se. Accordingly, the fatty carbonates can be constructed symmetrically or asymmetrically. However, carbonates are preferably used in which R ¹⁶ and R ^{18 are} identical and represent alkyl radicals having 16 to 22 carbon atoms. Transesterification products of dimethyl or diethyl carbonate with cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol and / or erucyl alcohol in the form of their mono- and diesters or their technical mixtures are particularly preferred.

Fatty acids. Aliphatic, optionally hydroxy-substituted carboxylic acids with 16 to 22 carbons, such as, for example, stearic acid, cetylstearic acid, hydroxystearic acid and behenic acid and their technical mixtures are suitable for this purpose.

Epoxy ring opening products. The ring opening products are known substances which are usually produced by acid-catalyzed reaction of terminal or internal olefin epoxides with aliphatic alcohols. The reaction products preferably follow the formula (X)

OH

in which R ¹⁸ and R ^{19 represent} hydrogen or an aikyl radical having 10 to 20 carbon atoms, with the proviso that the sum of the carbon atoms of R ¹⁸ and R ^{19 is} in the range from 10 to 20 and R ^{20 is} an alkyl and / or alkenyl radical having 12 to 22 carbon atoms and / or the radical of a polyol having 2 to 15 carbon atoms and 2 to 10 hydroxyl groups. Typical examples are ring opening products of α-dodecene epoxide, α-hexadecene epoxide, α-octadecene epoxide, α-eicosenepoxide, α-docosenepoxide, i-dodecenepoxide, i-hexadecenepoxide, i-octadecene epoxide, i-eicosenepoxide and / or i-docosenepoxide with lauryl alcohol, coconut oil alcohol, myristyl alcohol, cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, behenyl alcohol and / or erucyl alcohol. Ring opening products of hexa- and / or octadecene epoxides with fatty alcohols having 16 to 18 carbon atoms are preferably used. If, instead of the fatty alcohols, poiyols are used for the ring opening, the following substances are involved: glycerol; Alkylene glycols, such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons; technical oligoglycerol mixtures with a degree of self-condensation of 1.5 to 10 such as technical diglycerol mixtures with a diglycerol content of 40 to 50% by weight; Methyl compounds, such as, in particular, trimethylolethane, trimethylolpropane, trimethylolbutane, penta- erythritol and dipentaerythritol; Lower alkyl glucosides, especially those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside; Sugar alcohols with 5 to 12 carbon atoms, such as, for example, sorbitol or mannitol, sugars with 5 to 12 carbon atoms, such as, for example, glucose or sucrose; Aminosugars such as glucamine.

The proportion of pearlescent waxes in the surface-active agents can be 5 to 50 and preferably 10 to 35% by weight in the case of pearlescent concentrates. In the case of end products, such as pearlescent shampoos, the concentration is lower, namely 0.5 to 5 and preferably 1 to 2% by weight.

Industrial applicability

The cyclic carbonates have excellent anti-static and anti-static properties and even outperform the known silicone compounds on the market. Two further objects of the invention therefore relate to their use as a substitute for silicone oils in cosmetic and / or pharmaceutical preparations and as a finishing agent for the production of cosmetic preparations in which they are present in amounts of 1 to 50, preferably 3 to 30 and in particular 5 to 25% by weight. -% can be included.

Surface-active preparations

The preparations according to the invention are preferably cosmetic agents, such as, for example, hair shampoos, hair lotions, bubble baths, creams or lotions, which, as further auxiliaries and additives, include superfatting agents, stabilizers, consistency agents, thickeners, cation polymers, silicone compounds, film formers, preservatives, hydrotropes, Solubilizers, UV light protection filters, insect repellents, self-tanners, perfume oils, dyes and the like can contain.

Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers. Mainly fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides come into consideration as consistency agents. A combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred. Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxy

n methyl cellulose and hydroxyethyl cellulose, also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, (eg Carbopole® from Goodrich or Synthalene® from Sigma), polyacrylic amides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylol propane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides and electrolytes such as table salt and ammonium chloride.

Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethyl cellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone / vinyl imidazole polymers such as e.g. Luviquat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, e.g. Amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyaminopolyamides, e.g. described in FR-A 2252840 and its crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, condensation products of dihaloalkylene, such as e.g. Dibromobutane with bisdialkylamines, e.g. Bis-dimethylamino-1,3-propane, cationic guar gum, such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers such as e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.

Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature. Typical examples of fats are glycerides, waxes include Beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax or micro waxes, optionally in combination with hydrophilic waxes, e.g. Cetylstearyl alcohol or partial glycerides in question. Metal salts of fatty acids, such as e.g. Magnesium, aluminum and / or zinc stearate can be used. Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds. Montmorillonites, clay minerals, pemulene and alkyl-modified carbopol types (Goodrich) can serve as swelling agents for aqueous phases.

UV light protection filters are organic substances that are able to absorb ultraviolet rays and the absorbed energy in the form of longer-wave radiation, for example To give off heat again. UVB filters can be oil-soluble or water-soluble. Examples of oil-soluble substances are:

3-benzylidene camphor and its derivatives, e.g. 3- (4-methylbenzylidene) camphor;

4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoic acid 2-ethylhexyl ester, 4-

2-octyl (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;

Esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate, 2-ethylhexyl 4-methoxycinnamate, 2-ethylhexyl 2-cyano-3-phenylcinnamate (octocrylene);

Esters of salicylic acid, preferably salicylic acid 2-ethylhexyl ester, salicylic acid 4-isopropylbenzyl ester, salicylic acid homomethyl ester;

Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;

Esters of benzalmalonic acid, preferably di-2-ethylhexyl 4-methoxybenzmalonate;

Triazine derivatives, e.g. 2,4,6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and octyltriazone.

Propane-1,3-dione, e.g. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione;

Possible water-soluble substances are:

• 2-phenylbenzimidazole-5-sulfonic acid and its alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium salts;

• Sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;

Sulfonic acid derivatives of 3-benzylidene camphor, e.g. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and their salts.

Derivatives of benzoylmethane, such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione or 1-phenyl-3-, are particularly suitable as typical UV-A filters. (4'-isopropylphenyl) propane-1,3-dione. The UV-A and UV-B filters can of course also be used in mixtures. In addition to the soluble substances mentioned, insoluble pigments, namely finely dispersed metal oxides or salts, such as, for example, titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate are also suitable for this purpose. The particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, but it is also possible to use particles which have an ellipsoidal shape or shape which differs from the spherical shape in some other way. In addition to the two aforementioned groups of primary light stabilizers, secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin. Typical examples are superoxide Dismutase, tocopherols (vitamin E) and ascorbic acid (vitamin C). Further suitable UV light protection filters can be found in the overview by P.Finkel in SÖFW-Journal 122, 543 (1996).

Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior. Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are

• glycerin;

Alkylene glycols, such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;

Technical oligoglycerol mixtures with a degree of self-condensation of 1.5 to 10, such as technical diglycerol mixtures with a diglycerol content of 40 to 50% by weight;

• Methyl compounds, such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;

• Lower alkyl glucosides, in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;

Sugar alcohols with 5 to 12 carbon atoms, such as sorbitol or mannitol,

• Sugar with 5 to 12 carbon atoms, such as glucose or sucrose;

Aminosugars, such as glucamine.

Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid. N, N-diethyl-m-touluamide, 1, 2-pentanediol or Insect repellent 3535 are suitable as insect repellents, and dihydroxyacetone is suitable as a self-tanner.

Perfume oils include extracts from flowers (lavender, roses, jasmine, neroli), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway seeds, juniper), fruit peels (bergamot, lemon, oranges), roots (Macis, Angelica, Celery, Cardamom, Costus, Iris, Calmus), woods (sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme), needles and branches (spruce , Fir, pine, mountain pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials such as musk, civet and castoreum are also suitable. Ambroxan, eugenol, isoeugenol, citronellal, hydroxycitronellal, geraniol, citronellol, geranyl acetate, citral, ionone and methylionone are suitable as synthetic or semi-synthetic perfume oils.

The dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as described, for example, in the publication "Cosmetic Dyes" by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106 are put together. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.

The total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition. The agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.

Examples

• Example 1, comparative example V1. The wet combability was investigated when using a shampoo according to the invention with glycerol carbonate and a comparison mixture with silicone oil. The comparison shows that the recipe with glycerol carbonate is significantly more effective.

• Example 2, comparative example V2. The anti-dandruff climbazole was incorporated into a formulation with and without glycerol carbonate while heating. Formulation 2 according to the invention was clear and remained stable even at storage at 40 ° C. for at least 4 weeks. The comparison formulation V2 was cloudy and segregated within a few hours.

• Examples 3 to 5. The preparations according to the invention reproduce example formulations for hair treatments with glycerol carbonate as emulsifier.

The results are summarized in Table 1.

Table 1

Application results (quantities as% by weight of active substance)

Claims

claims

1. Use of cyclic carbonates of the formula (I),

in which R ¹ and R ² independently of one another represent hydrogen or optionally hydroxy-substituted alkyl radicals having 1 to 30 carbon atoms, as emulsifiers for the preparation of surface-active preparations.

2. Use according to claim 1, characterized in that one uses glycerol carbonate.

3. Use according to claims 1 and 2, characterized in that the cyclic carbonates are used together with anionic, nonionic, cationic, amphoteric and / or zwitterionic surfactants.

4. Use according to claim 3, characterized in that the cyclic carbonates are used together with alkyl ether sulfates and / or alkyl and / or alkenyl oligoglycosides.

5. Use according to claims 1 to 4, characterized in that the cyclic carbonates are used together with oil bodies which are selected from the group formed by Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, Esters of linear Cθ-C∑Q fatty acids with linear Cδ-C∑o fatty alcohols, esters of branched C6-Ci3 carboxylic acids with linear Cθ-C∑o fatty alcohols, esters of linear CΘ-Ciδ fatty acids with branched alcohols, Esters of linear and / or branched fatty acids with polyhydric alcohols and / or Guerbet alcohols, triglycerides based on Cδ-Cio fatty acids, esters of Cδ-C22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, dicarboxylic acid esters, vegetable oils, branched primary alcohols substituted cyclohexanes, dialkyl carbonates, Guerbet carbonates, dialkyl ethene, ring opening products of epoxidized fatty acid esters with polyols, Silicone oils and / or aliphatic or naphthenic hydrocarbons.

. Use according to claims 1 to 5, characterized in that the cyclic carbonates are used together with co-emulsifiers which are selected from the group formed by:

(a1) Adducts of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 C atoms, with fatty acids with 12 to 22 C atoms and with alkylphenols with 8 to 15 C atoms in the Alkyl group;

(a3) glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and their ethylene oxide addition products;

(a6) polyol esters;

(a8) partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols, alkyl glucosides and polyglucosides;

(a9) trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates;

(a10) wool wax alcohols;

(a11) polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives;

(a12) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol and / or mixed esters of fatty acids with 6 to 22 carbon atoms, methyl glucose and polyols and

(a13) polyalkylene glycols.

7. Use according to claims 1 to 6, characterized in that the cyclic carbonates are used together with active ingredients.

8. Use according to claims 1 to 7, characterized in that the cyclic carbonates are used together with pearlescent waxes which are selected from the group formed by:

(b1) alkylene glycol esters, (b2) fatty acid alkanolamides, (b3) partial glycerides,

(b4) esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms,

(b5) fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and / or fatty carbonates which have a total of at least 24 carbon atoms,

(b6) fatty acids and hydroxy fatty acids with 16 to 22 carbon atoms; such as

(b6) Ring opening products of olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15 carbon atoms and 2 to 10 hydroxyl groups.

9. Use of cyclic carbonates as a substitute for silicone oils in cosmetic and / or pharmaceutical preparations.

10. Use of cyclic carbonates as a finishing agent for the production of cosmetic preparations.