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EP0788537B1 - Detergent aqueux pour lavage manuel de la vaisselle - Google Patents

Detergent aqueux pour lavage manuel de la vaisselle Download PDF

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Publication number
EP0788537B1
EP0788537B1 EP95935954A EP95935954A EP0788537B1 EP 0788537 B1 EP0788537 B1 EP 0788537B1 EP 95935954 A EP95935954 A EP 95935954A EP 95935954 A EP95935954 A EP 95935954A EP 0788537 B1 EP0788537 B1 EP 0788537B1
Authority
EP
European Patent Office
Prior art keywords
weight
alkyl
alcohol
sulfate
glycerol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP95935954A
Other languages
German (de)
English (en)
Other versions
EP0788537A1 (fr
Inventor
Udo Hees
Ansgar Behler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0788537A1 publication Critical patent/EP0788537A1/fr
Application granted granted Critical
Publication of EP0788537B1 publication Critical patent/EP0788537B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3409—Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the present invention relates to the use of glycerol sulfates in aqueous, manually applicable dishwashing detergents with strong Foam development and good cleaning power.
  • Liquid cleaning agents usually consist of aqueous solutions of synthetic anionic and / or nonionic surfactants and conventional additives. They are particularly useful for cleaning hard surfaces Example of glass, ceramic materials, plastics, lacquered and polished surfaces used.
  • An important area of application for liquid The cleaning agent is the manual rinsing of EB and cookware.
  • the dishes are usually cleaned at slightly elevated temperatures from about 35 to 45 ° C in very dilute liquors. Doing so from the consumer the cleaning power of an agent in general as all the more better judged, the stronger and the longer the cleaning liquor foams. Because of the contact of the hands with the cleaning solution over a longer period When washing dishes manually, the period is also skin-friendliness the agent of particular importance. For these reasons, the Expert in the selection of components and the composition of a Considerations other than manual cleaning of dishes with liquid cleaning agents for other hard surfaces.
  • German published patent application DE 40 38 478 relates to a process for the preparation of partial glyceride sulfates by reacting mixtures consisting of triglycerides and glycerol with gaseous sulfur trioxide and subsequent neutralization of the reaction products with aqueous bases.
  • the sulfonation products obtained are complex mixtures which also contain up to 3.2% by weight of open-chain and cyclic glycerol sulfates.
  • the object of the present invention is to provide detergent preparations, in particular to provide aqueous hand dishwashing detergents with a high total surfactant content.
  • the object was achieved by using glycerol sulfates as Solubilizer; especially when the total surfactant content is more than 25 % By weight, preferably more than 33% by weight, based on the total hand dishwashing detergent, Glycerol sulfates are suitable solubilizers.
  • trisulfated glycerol is particularly suitable, but also mono- or disulfated glycerol and any mixture is suitable as a solubilizer.
  • the preparation of the glycerol sulfate can e.g. B. by reaction of glycerol with gaseous SO 3 , a synthesis instruction is disclosed in the example part.
  • Particularly suitable surfactants are C 6 -C 22 alkyl sulfates and / or C 6 -C 22 alkyl ether sulfates and / or C 9 -C 13 alkyl benzene sulfonates.
  • Another object of the invention is therefore the use of glycerol sulfates in C 6 -C 22 alkyl sulfate and / or C 6 -C 22 alkyl ether sulfate and / or C 9 -C 13 alkyl benzene sulfonate-containing aqueous hand dishwashing detergents.
  • Fatty alkyl sulfates which can be used in the sense of the invention follow the formula II, R 2 -O-SO 3 X, in which R 2 represents a saturated or unsaturated C 6 -C 22 alkyl group and X represents an alkali or alkaline earth metal.
  • These substances are known chemical compounds that can be obtained by sulfating fatty alcohols.
  • Typical examples are the sulfates of capronic alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol and technical-grade erucyl alcohol.
  • Sulfates of technical grade C 12/14 or C 12/18 coconut fatty alcohol cuts are preferably used in the form of their sodium or Mg salts.
  • Fatty alkyl ether sulfates which can be used in the sense of the invention follow the formula III, R 3 O- (CH 2 CH 2 O) n -SO 3 X in which R 3 is a saturated or unsaturated C 6 -C 22 alkyl group, n is a number from 1 to 10 and X is an alkali or alkaline earth metal.
  • Typical examples are the sulfation products of adducts from 1 to 10 moles of ethylene oxide (conventional or narrow homolog distribution) 1 mol each of capronic alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, Myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, oleyl alcohol, Elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, Behenyl alcohol and erucyl alcohol and their technical mixtures.
  • Sulfates of adducts of 2 to 7 moles of ethylene oxide to saturated are preferred Coconut fatty alcohols with 12 to 18 carbon atoms in the form of their sodium, Potassium and / or magnesium salts.
  • C 9 -C 13 alkylbenzenesulfonates which can be used for the purposes of the invention are, for example, the products sold under the trade names Marlon (from Hüls) and Witconate (from Witco).
  • surfactant mixtures which additionally contain a C 6 -C 22 -alkyl glycoside.
  • Aqueous detergent compositions in the sense of the invention are e.g. B. Bubble baths, hair shampoos and in particular hand dishwashing detergents.
  • the total surfactant content in these agents is over 25% by weight, in particular over 33% by weight, based on the total agent.
  • Alkyl glycosides are known substances that can be obtained by the relevant methods of preparative organic chemistry. Representative of the extensive literature, reference is made here to the documents EP-A1-0 301 298 and WO 90/3977.
  • the alkyl glycosides follow the formula IV, R 4 O [G] x , in which R 4 is a linear or branched, saturated or unsaturated alkyl radical having 6 to 22 carbon atoms, [G] is a glycose radical and x is a number from 1 to 10.
  • the alkyl or alkenyl radical R 4 can be derived from primary alcohols having 6 to 22, preferably 12 to 18, carbon atoms. Typical examples are capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as those obtained in the course of the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 4 is preferably derived from lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol or oleyl alcohol.
  • anionic surfactants are e.g. B. alkanesulfonates with 10 to 20, preferably 12 to 18 carbon atoms in the alkyl radical and olefin sulfonates 12 to 16, preferably 12 to 14 carbon atoms in the n-alkyl radical name that in amounts of up to 50 wt .-%, based on the total agent, can be included.
  • Soaps ie alkali metal or ammonium salts of saturated or unsaturated C 6 -C 22 fatty acids, are preferably not contained in the agents according to the invention because of their foam-suppressing properties.
  • surfactants optionally contained in the agents according to the invention are amphoteric surfactants and non-ionic surfactants.
  • Betaine compounds of the formula can be used as amphoteric surfactants are used in which R 5 is an alkyl radical with 8 to 25, preferably 10 to 21 carbon atoms and R 6 and R 7 , which are optionally interrupted by heteroatoms or heteroatom groups, and R 6 and R 7 are identical or different alkyl radicals with 1 to 3 carbon atoms.
  • R 5 is an alkyl radical with 8 to 25, preferably 10 to 21 carbon atoms and R 6 and R 7 , which are optionally interrupted by heteroatoms or heteroatom groups, and R 6 and R 7 are identical or different alkyl radicals with 1 to 3 carbon atoms.
  • Preferred are C 10 -C 18 alkyl dimethyl carboxymethyl betaine and C 11 -C 17 alkyl amidopropyl dimethyl carboxymethyl betaine.
  • fatty acid alkanolamides e.g. B. C 12/18 fatty acid monoethanolamide or adducts of 4 to 20, preferably 4 to 10 moles of alkylene oxide, preferably ethylene oxide to C 10 -C 20 , preferably C 12 -C 18 alkanols, but also the adducts of ethylene oxide to polypropylene glycols , which are known under the name Pluronics (R) , and addition products of 1 to 7 mol of ethylene oxide onto C 12 -C 18 alkanols reacted with 1 to 5 mol of propylene oxide are suitable.
  • Pluronics (R) Pluronics
  • Fatty alkyl amine oxides are also suitable.
  • the solvents to be added if necessary are low molecular weight Alkanols with 1 to 4 carbon atoms in the molecule, preferably around ethanol and isopropanol.
  • Dyes and perfume oils can optionally include, for example, alkanolamines, Polyols such as ethylene glycol, propylene glycol, glycerin as well Alkylbenzenesulfonates with 1 to 3 carbon atoms in the alkyl radical are used.
  • the preferred thickeners include urea and ammonium chloride, which can also be used in combination.
  • urea and ammonium chloride which can also be used in combination.
  • a preservative Examples include sodium benzoate, formaldehyde and sodium sulfite call.
  • the agents according to the invention can also be conventional disinfectants contain.
  • the pH of the agents according to the invention is preferably between 5.0 and 7.5.
  • a glycerol sulfate thus prepared was used for the following application examples used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cleaning Implements For Floors, Carpets, Furniture, Walls, And The Like (AREA)

Claims (6)

  1. Utilisation de sulfates de glycérol en tant qu'agent solubilisant dans des liquides aqueux de lavage de la vaisselle à la main.
  2. Utilisation de sulfates de glycérol selon la revendication 1
    dans des liquides aqueux de lavage de la vaisselle à la main, ayant une teneur totale en agents tensioactifs de plus de 25 % en poids, de préférence de plus de 33 % en poids, rapporté au liquide de lavage de la vaisselle à la main aqueux total.
  3. Utilisation selon la revendication 1 et la revendication 2
    dans des liquides aqueux de lavage de la vaisselle à la main, contenant des alkyles sulfates (en C6 à C22) et/ou des alkyles éther sulfates (en C6 à C22) et/ou des alkyles benzène sulfonates (en C9 à C13).
  4. Compositions aqueuses de détergents, en particulier de produit de lavage de la vaisselle à la main qui contiennent :
    a) de 0,2 % en poids à 10 % en poids, de préférence de 1 % en poids à 5 % en poids d'un sulfate de glycérol,
    b) de 1 % en poids à 50 % en poids de préférence de 5 % en poids à 45 % en poids d'un alkyle sulfate (en C6 à C22), d'un alkyle éther sulfate (en C6 à C22), d'un alkyle benzène sulfonate (en C9 à C13) ou d'un mélange quelconque des agents tensioactifs cités.
    c) de 1 % en poids à 20 % en poids de préférence de 2 % en poids à 10 % en poids, à chaque fois rapporté au produit total, d'un alkylglycoside de formule IV, R4O[G]x dans laquelle R4 représente un radical alkyle saturé ou non saturé en C6 à C22, G représente un reste de glycose et x représente des nombres allant de 1 à 10.
  5. Agent selon la revendication 4,
    caractérisé en ce que
    la teneur totale en agent tensioactif s'élève à plus de 25 % en poids, de préférence à plus de 33 % en poids rapporté à la composition totale de détergent.
  6. Agent selon la revendication 4 et la revendication 5,
    caractérisé en ce qu'
    il est dépourvu de sels de métal alcalin ou d'ammonium d'acides gras saturés ou non saturés en C6 à C22.
EP95935954A 1994-10-28 1995-10-20 Detergent aqueux pour lavage manuel de la vaisselle Expired - Lifetime EP0788537B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4438583A DE4438583A1 (de) 1994-10-28 1994-10-28 Wäßrige Handgeschirrspülmittel
DE4438583 1994-10-28
PCT/EP1995/004124 WO1996013567A1 (fr) 1994-10-28 1995-10-20 Detergent aqueux pour lavage manuel de la vaisselle

Publications (2)

Publication Number Publication Date
EP0788537A1 EP0788537A1 (fr) 1997-08-13
EP0788537B1 true EP0788537B1 (fr) 1999-04-21

Family

ID=6531951

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95935954A Expired - Lifetime EP0788537B1 (fr) 1994-10-28 1995-10-20 Detergent aqueux pour lavage manuel de la vaisselle

Country Status (8)

Country Link
US (1) US6090764A (fr)
EP (1) EP0788537B1 (fr)
AT (1) ATE179208T1 (fr)
DE (2) DE4438583A1 (fr)
DK (1) DK0788537T3 (fr)
ES (1) ES2132726T3 (fr)
GR (1) GR3030184T3 (fr)
WO (1) WO1996013567A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19714043C2 (de) * 1997-04-05 2002-09-26 Cognis Deutschland Gmbh Verwendung von Glycerinsulfaten als Viskositätsregulatoren für konzentrierte wäßrige Alkyl(ether)sulfatpasten
US6683036B2 (en) * 2000-07-19 2004-01-27 The Procter & Gamble Company Cleaning composition
MX2007015393A (es) * 2005-06-23 2008-02-19 Reckitt Benckiser Inc Composiciones detergentes para lavar vajillas para trabajo ligero.

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2979521A (en) * 1955-02-09 1961-04-11 Colgate Palmolive Co Preparation of glycerol sulfuric acids
US3250202A (en) * 1963-08-28 1966-05-10 Polaroid Corp Photographic apparatus
US3256202A (en) * 1964-06-01 1966-06-14 Alcolac Chemical Corp Surface-active agents and detergent compositions
US4024078A (en) * 1975-03-31 1977-05-17 The Procter & Gamble Company Liquid detergent composition
US4692271B1 (en) * 1977-12-09 1997-07-22 Albright & Wilson Concentrated aqueous surfactant compositions
US4753754B1 (en) * 1977-12-09 1997-05-13 Albright & Wilson Concentrated aqueous surfactant compositions
DE3534082A1 (de) * 1985-09-25 1987-04-02 Henkel Kgaa Fluessiges reinigungsmittel
DE3723826A1 (de) * 1987-07-18 1989-01-26 Henkel Kgaa Verfahren zur herstellung von alkylglykosiden
DE3833780A1 (de) * 1988-10-05 1990-04-12 Henkel Kgaa Verfahren zur direkten herstellung von alkylglykosiden
US5576425A (en) * 1988-10-05 1996-11-19 Henkel Kommanditgesellschaft Auf Aktien Process for the direct production of alkyl glycosides
DE3933860A1 (de) * 1989-10-11 1991-04-18 Henkel Kgaa Verfahren zur herstellung von alkyl-polyethoxyethersulfaten
DE3936001A1 (de) * 1989-10-28 1991-05-02 Henkel Kgaa Verfahren zur sulfierung ungesaettigter fettsaeureglycerinester
DE4038478A1 (de) * 1990-12-03 1992-06-04 Henkel Kgaa Verfahren zur herstellung von partialglyceridsulfaten
DE4038477A1 (de) * 1990-12-03 1992-06-04 Henkel Kgaa Verfahren zur kontinuierlichen herstellung von partialglyceridsulfaten
US5580849A (en) * 1992-09-01 1996-12-03 The Procter & Gamble Company Liquid or gel detergent compositions containing calcium and stabilizing agent thereof
DE4234487A1 (de) * 1992-10-14 1994-04-21 Henkel Kgaa Wäßrige Detergensgemische

Also Published As

Publication number Publication date
DE4438583A1 (de) 1996-05-02
DE59505724D1 (de) 1999-05-27
ATE179208T1 (de) 1999-05-15
ES2132726T3 (es) 1999-08-16
US6090764A (en) 2000-07-18
WO1996013567A1 (fr) 1996-05-09
GR3030184T3 (en) 1999-08-31
EP0788537A1 (fr) 1997-08-13
DK0788537T3 (da) 1999-11-01

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