EP0763591B1 - Produit pour laver la vaiselle à la main - Google Patents

Produit pour laver la vaiselle à la main Download PDF

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Publication number
EP0763591B1
EP0763591B1 EP96114276A EP96114276A EP0763591B1 EP 0763591 B1 EP0763591 B1 EP 0763591B1 EP 96114276 A EP96114276 A EP 96114276A EP 96114276 A EP96114276 A EP 96114276A EP 0763591 B1 EP0763591 B1 EP 0763591B1
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EP
European Patent Office
Prior art keywords
alkyl
carbon atoms
alcohol
formula
alkenyl
Prior art date
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Expired - Lifetime
Application number
EP96114276A
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German (de)
English (en)
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EP0763591A1 (fr
Inventor
Karl Heinz Dr. Schmid
Andreas Dr. Syldath
Michael Elsner
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.)
BASF Personal Care and Nutrition GmbH
Cognis Chemie GmbH and Co KG
Original Assignee
Cognis Deutschland GmbH and Co KG
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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
    • C11D1/02—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
    • C11D1/83—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
    • 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
    • C11D1/02—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
    • C11D1/146—Sulfuric acid esters
    • 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 invention relates to aqueous hand dishwashing detergents with improved emulsifying power. containing defined amounts of low ethoxylated fatty alcohol ether sulfates in the form of their Magnesium salts.
  • Hand dishwashing detergents are usually dilute aqueous detergent mixtures represents, in addition to anionic surfactants, especially non-ionic and amphoteric Contain surfactants.
  • anionic surfactants especially non-ionic and amphoteric Contain surfactants.
  • these agents also have to meet the requirements a strong and stable foam, which does not even with considerable fat load collapses - even if this property does not directly affect the cleaning performance related.
  • one particular problem is the detached one to emulsify lipophilic dirt, i.e. to prevent redeposition on the dishes. Products of the state of the art also show deficits here.
  • HGSM based on fatty alcohol ether sulfate sodium salts, enzymes and magnesium ions are proposed.
  • HGSM are known from international patent applications WO 92/06156, WO 94/05769 and WO 94/24241 (Procter & Gamble), which contain combinations of anionic surfactants and glucamides, ether carboxylic acids or secondary alkyl sulfates with magnesium ions.
  • the complex object of the invention was therefore to provide aqueous hand dishwashing detergents to make available that at the same time have a good dishwashing capacity, a high base foam, good fat resistance and in particular an excellent emulsifying power feature.
  • the invention relates to aqueous hand dishwashing detergents containing fatty alcohol ether sulfates of the formula ( I ), R 1 O (CH 2 CH 2 O) n SO 3 Mg (I) in which R 1 is an alkyl and / or alkenyl radical having 8 to 18 carbon atoms and n is a number from 0.5 to 1.5, in amounts of 40 to 90% by weight, based on the proportion of detergent substance and as further surfactants alkyl and alkenyl oligoglycosides of the formula (II) , R 2 O- [G] p (II) in which R 2 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10.
  • the fatty alcohol ether sulfates are present in amounts of preferably 45 to 90 and in particular 45 to 80% by weight, based on the proportion of detergent substance.
  • the condition is that the proportion of the above-mentioned magnesium salts - based on the Share of active detergent, i.e. surfactant - is above a critical limit.
  • the agents can be used as further surfactants Betaines and / or fatty alcohol sulfates contain.
  • the fatty alcohol sulfates to be used for the purposes of the invention are substances known per se which, by the addition of very little, namely an average of 0.5 to 1.5, preferably about 1 mol, of ethylene oxide to a technical coconut fatty alcohol containing 8 to 18 and preferably 12 up to 14 carbon atoms, sulfation of the polyglycol ether and neutralization with a basic magnesium salt.
  • magnesium salt surfactants is from H.Plate in Parf. Cosm. 76 , 28 (1995) .
  • Alkyl and alkenyl oligoglycosides are known nonionic surfactants which follow the formula (II) R 2 O- [G] p (II) in which R 2 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10. They can be obtained according to the relevant procedures in preparative organic chemistry. As representative of the extensive literature, reference is made here to the documents EP-A1-0 301 298 and WO 90/03977 .
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose. The preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligo glucosides .
  • the alkyl or alkenyl radical R 2 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in 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 2 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above. Alkyl oligoglucosides based on hardened C 12/14 coconut alcohol with a DP of 1 to 3 are preferred.
  • Betaines are known surfactants which are predominantly produced by carboxyalkylation, preferably carboxymethylation, of aminic compounds.
  • the starting materials are preferably condensed with halocarboxylic acids or their salts, in particular with sodium chloroacetate, one mol of salt being formed per mole of betaine.
  • unsaturated carboxylic acids such as acrylic acid is also possible.
  • betaines and "real" amphoteric surfactants reference is made to the contribution by U.Ploog in Seifen- ⁇ le-Fette-Wwachs, 198, 373 (1982) . Further overviews on this topic can be found for example by A. O'Lennick et al.
  • betaines are the carboxyalkylation products of secondary and in particular tertiary amines which follow the formula (III) in which R 3 for alkyl and / or alkenyl radicals with 6 to 22 carbon atoms, R 4 for hydrogen or alkyl radicals with 1 to 4 carbon atoms, R 5 for alkyl radicals with 1 to 4 carbon atoms, n for numbers from 1 to 6 and X for a Alkali and / or alkaline earth metal or ammonium.
  • R 3 for alkyl and / or alkenyl radicals with 6 to 22 carbon atoms
  • R 4 for hydrogen or alkyl radicals with 1 to 4 carbon atoms
  • R 5 for alkyl radicals with 1 to 4 carbon atoms
  • n for numbers from 1 to 6
  • X for a Alkali and / or alkaline earth metal or ammonium.
  • Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecylmethylamine, dodecyldimethylamine, Dodecylethylmethylamin, C 12/14 -Kokosalkyldimethylamin, myristyldimethylamine, cetyldimethylamine, stearyldimethylamine, stearyl, oleyl, C 16/18 tallow alkyl dimethyl amine and technical mixtures thereof.
  • R 6 CO represents an aliphatic acyl radical having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds
  • m represents numbers from 1 to 3
  • R 4 , R 5 , n and X have the meanings given above.
  • Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, namely caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, gadoleic acid and arachic acid, arachic acid and their technical mixtures, with N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, N, N-diethylaminoethylamine and N, N-diethylaminopropylamine, which are condensed with sodium chloroacetate. It is preferred to use a condensation product of C 8/18 coconut fatty acid N, N-dimethylaminopropylamide with sodium chloroacetate.
  • suitable starting materials for the betaines to be used in accordance with the invention are also imidazolines which follow the formula (V) in which R 7 is an alkyl radical having 5 to 21 carbon atoms, R 8 is a hydroxyl group, an OCOR 7 or NHCOR 7 radical and m is 2 or 3.
  • R 7 is an alkyl radical having 5 to 21 carbon atoms
  • R 8 is a hydroxyl group
  • an OCOR 7 or NHCOR 7 radical an hydroxyl group
  • m is 2 or 3.
  • These substances are also known substances which can be obtained, for example, by cyclizing condensation of 1 or 2 moles of fatty acid with polyhydric amines such as, for example, aminoethylethanolamine (AEEA) or diethylene triamine.
  • AEEA aminoethylethanolamine
  • the corresponding carboxyalkylation products are mixtures of different open-chain betaines.
  • Typical examples are condensation products of the above-mentioned fatty acids with AEEA, preferably imidazolines based on lauric acid or again C 12/14 coconut fatty acid, which are subsequently betainized with sodium chloroacetate.
  • Alkyl and / or alkenyl sulfates which are also often referred to as fatty alcohol sulfates, are to be understood as meaning the sulfation products of primary alcohols which follow the formula ( VI ) R 9 O-SO 3 Z (VI) in which R 9 is a linear or branched, aliphatic alkyl and / or alkenyl radical having 6 to 22, preferably 12 to 18 carbon atoms and Z is an alkali metal and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
  • alkyl sulfates which can be used for the purposes of the invention are the sulfation products of capron alcohol, caprylic alcohol, capric alcohol, 2-ethylhexyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, arachelyl alcohol, aridyl alcohol, ela-elyl alcohol, ela-alcohol alcohol, and erucyl alcohol and their technical mixtures, which are obtained by high pressure hydrogenation of technical methyl ester fractions or aldehydes from Roelen's oxosynthesis.
  • the sulfation products can preferably be used in the form of their alkali metal salts, and especially their sodium salts.
  • Alkyl sulfates based on C 16/18 tallow fatty alcohols or vegetable fatty alcohols of comparable C chain distribution in the form of their sodium, ammonium and / or magnesium salts are particularly preferred.
  • the aqueous hand dishwashing detergents contain the following ingredients: 40 to 100 (45 to 80)% by weight coconut fatty alcohol + 1EO sulfate magnesium salt, 0 to 35 (20 to 30)% by weight of alkyl sulfates (for example lauryl sulfate ammonium salt), 5 to 15 % By weight alkyl glucosides (eg coconut alkyl oligoglucoside) and 0 to 15 (5 to 15)% by weight betaines (e.g. coconut fatty acid amidobetaine).
  • alkyl sulfates for example lauryl sulfate ammonium salt
  • alkyl glucosides eg coconut alkyl oligoglucoside
  • betaines e.g. coconut fatty acid amidobetaine
  • the percentages relate to the proportion of detergent and complement each other 100% by weight.
  • the preferred ranges are given in brackets.
  • the agents according to the invention usually have a proportion of wash-active substance in the range of 5 to 40 and preferably 15 to 25% by weight. They are characterized by excellent dishwashing ability, high base foam, fat resistance and a particularly advantageous emulsifying power. Furthermore, they can be conventional components of dishwashing detergents such as builders (polycarboxylates, EDTA, NTA, Citric acid), alkalis, solubilizers (ethanol, propylene glycol, toluenesulfonate, cumene sulfonate), Dyes and fragrances included.
  • dishwashing detergents such as builders (polycarboxylates, EDTA, NTA, Citric acid), alkalis, solubilizers (ethanol, propylene glycol, toluenesulfonate, cumene sulfonate), Dyes and fragrances included.
  • still fatty alcohol ether sulfate sodium or ammonium salts, sulfosuccinates, monoglyceride sulfates, Fatty alcohol polyglycol ethers, fatty acid N-alkyl glucamides, protein hydrolyzates, protein fatty acid condensates and / or amine oxides may be included.

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  • 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)

Claims (5)

  1. Produits pour le lavage à la main de la vaisselle, aqueux qui contiennent des étherssulfates d'alcool gras de formule (I), R1O(CH2CH2O)nSO3Mg dans laquelle R1 représente un radical alkyle et/ou alkényle ayant de 8 à 18 atomes de carbone, et n représente des nombres allant de 0,5 à 1,5, en quantité de 40 à 90 % en poids rapporté à la partie de substance active pour le lavage, et comme agents tensioactifs supplémentaires des alkyle et alkényloligoglycosides de formule (II), R2O-[G]p dans laquelle R2 représente un radical alkyle et/ou alkényle ayant de 4 à 22 atomes de carbone, G représente un reste de sucre ayant 5 ou 6 atomes de carbone et p représente un nombre allant de 1 à 10.
  2. Produits selon la revendication 1,
    caractérisés en ce qu'
    ils renferment comme agents tensioactifs supplémentaires des bétaïnes de formule (III),
    Figure 00160001
    dans laquelle R3 représente un radical alkyle et/ou alkényle ayant de 6 à 22 atomes de carbone, R4 représente de l'hydrogène ou un radical alkyle ayant de 1 à 4 atomes de carbone, R5 représente un radical alkyle ayant de 1 à 4 atomes de carbone, n représente un nombre allant de 1 à 6 et X représente un métal alcalin et/ou alcalino-terreux ou ammonium.
  3. Produits selon les revendications 1 à 2,
    caractérisés en ce qu'
    ils renferment comme agents tensioactifs supplémentaires une bétaïne de formule (IV),
    Figure 00170001
    dans laquelle R6CO représente un reste acyle aliphatique ayant de 6 à 22 atomes de carbone et 0 ou de 1 à 3 double liaisons, m représente un nombre allant de 1 à 3 et R4, R5, n et X ont les significations mentionnées ci-dessus.
  4. Produits selon les revendications 1 à 3,
    caractérisés en ce qu'
    ils renferment comme agents tensioactifs supplémentaires des alkyl- et/ou alkényl sulfates de formule (VI) R9O-SO3Z dans laquelle R9 représente un radical alkyle et/ou alkényle aliphatique, linéaire ou ramifié ayant de 6 à 22, de préférence de 12 à 18 atomes de carbone et Z représente un métal alcalin, et/ou alcalino-terreux, un ammonium, un alkylammonium, un alkanolammonium ou un glucammonium.
  5. Produits selon les revendications 1 à 4,
    caractérisés en ce qu'
    ils possèdent une proportion de substance active pour le lavage, dans la zone de 5 à 40 % en poids.
EP96114276A 1995-09-15 1996-09-06 Produit pour laver la vaiselle à la main Expired - Lifetime EP0763591B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19534369A DE19534369C2 (de) 1995-09-15 1995-09-15 Wäßrige Handgeschirrspülmittel
DE19534369 1995-09-15

Publications (2)

Publication Number Publication Date
EP0763591A1 EP0763591A1 (fr) 1997-03-19
EP0763591B1 true EP0763591B1 (fr) 2000-12-13

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EP96114276A Expired - Lifetime EP0763591B1 (fr) 1995-09-15 1996-09-06 Produit pour laver la vaiselle à la main

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EP (1) EP0763591B1 (fr)
DE (2) DE19534369C2 (fr)
ES (1) ES2153925T3 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10329521B2 (en) 2014-05-21 2019-06-25 Colgate-Palmolive Company Aqueous liquid dishwashing composition comprising an ammonium alkyl ether sulfate and alkylamidopropyl betaine

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999010463A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Detergents aqueux pour laver la vaisselle a la main
FR2826017B1 (fr) 2001-06-15 2004-06-11 Cognis France Sa Melanges de tensioactifs
DE102007032110A1 (de) * 2007-07-09 2009-01-15 Henkel Ag & Co. Kgaa Wasch- oder Reinigungsmittel mit Tensiden auf Basis nachwachsender Rohstoffe
EP2179018A2 (fr) * 2007-08-17 2010-04-28 Reckitt Benckiser Inc. Compositions de traitement de surfaces dures, acceptables d'un point de vue environnemental

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4316824A (en) * 1980-06-26 1982-02-23 The Procter & Gamble Company Liquid detergent composition containing alkyl sulfate and alkyl ethoxylated sulfate
GB8313348D0 (en) * 1983-05-14 1983-06-22 Procter & Gamble Ltd Liquid detergent compositions
EP0157443B1 (fr) * 1984-03-19 1988-05-18 THE PROCTER & GAMBLE COMPANY Composition détergente contenant un détergent semi-polaire nonionique, un détergent anionique à base de métal alcalino-terreux et un détergent amidoalcyltétaine
DE4003098A1 (de) * 1990-02-02 1991-08-08 Henkel Kgaa Waessriges fluessiges reinigungsmittel
US5223179A (en) * 1992-03-26 1993-06-29 The Procter & Gamble Company Cleaning compositions with glycerol amides
CA2160229C (fr) * 1993-04-08 1999-01-26 Bruce Prentiss Murch Compositions detergentes renfermant du magnesium, sous forme de liquide, de gel ou d'autres milieux stables, avec des surfactifs a base de sulfate d'alkyle secondaire (2,3)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10329521B2 (en) 2014-05-21 2019-06-25 Colgate-Palmolive Company Aqueous liquid dishwashing composition comprising an ammonium alkyl ether sulfate and alkylamidopropyl betaine

Also Published As

Publication number Publication date
ES2153925T3 (es) 2001-03-16
DE59606206D1 (de) 2001-01-18
EP0763591A1 (fr) 1997-03-19
DE19534369C2 (de) 2000-06-15
DE19534369A1 (de) 1997-03-20

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