EP0814150A2 - Mélanges de surfactifs de sulphonates d'acyloxyalcanes et d'esters d'acides gras - Google Patents

Mélanges de surfactifs de sulphonates d'acyloxyalcanes et d'esters d'acides gras Download PDF

Info

Publication number: EP0814150A2
Authority: EP; European Patent Office
Prior art keywords: fatty acid; alkyl ester; acyloxyalkanesulfonate; content; acid
Prior art date: 1996-05-23
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP97108097A

Other languages

German (de)

English (en)

Other versions

EP0814150A3 (fr

Inventor

Bernd Dr. Nestler

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.)

Clariant Produkte Deutschland GmbH

Original Assignee

Clariant GmbH

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.)

1996-05-23

Filing date

1997-05-20

Publication date

1997-12-29

1997-05-20 Application filed by Clariant GmbH filed Critical Clariant GmbH

1997-12-29 Publication of EP0814150A2 publication Critical patent/EP0814150A2/fr

1999-02-10 Publication of EP0814150A3 publication Critical patent/EP0814150A3/fr

Status Withdrawn legal-status Critical Current

Links

235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 55
239000000194 fatty acid Substances 0.000 title claims abstract description 55
229930195729 fatty acid Natural products 0.000 title claims abstract description 55
239000000203 mixture Substances 0.000 title claims abstract description 18
239000004094 surface-active agent Substances 0.000 title claims abstract description 13
-1 fatty acid esters Chemical class 0.000 title description 9
150000004665 fatty acids Chemical class 0.000 claims abstract description 41
125000005907 alkyl ester group Chemical group 0.000 claims abstract description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
235000013162 Cocos nucifera Nutrition 0.000 description 12
244000060011 Cocos nucifera Species 0.000 description 12
238000005886 esterification reaction Methods 0.000 description 9
230000032050 esterification Effects 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 7
235000021588 free fatty acids Nutrition 0.000 description 7
238000000034 method Methods 0.000 description 6
235000021355 Stearic acid Nutrition 0.000 description 5
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
239000000344 soap Substances 0.000 description 5
229940079776 sodium cocoyl isethionate Drugs 0.000 description 5
239000008117 stearic acid Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
238000001816 cooling Methods 0.000 description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
235000019387 fatty acid methyl ester Nutrition 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000003760 tallow Substances 0.000 description 2
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
235000020661 alpha-linolenic acid Nutrition 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000012459 cleaning agent Substances 0.000 description 1
QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229960004488 linolenic acid Drugs 0.000 description 1
KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229940045998 sodium isethionate Drugs 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

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
- C11D1/66—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
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- 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
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
- 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
- C11D1/667—Neutral esters, e.g. sorbitan esters

Definitions

Acyloxyalkanesulfonates are anionic surfactants, which are mainly used in solid cleaning agents such as bar soaps. These surfactants are usually prepared by the process of so-called direct esterification by reacting sodium isethionate with an excess of a free fatty acid. In this reaction, the viscosity of the reaction mixture increases sharply with increasing esterification. It has therefore proven necessary to add so-called consistency regulators so that the highly viscous reaction mass remains sufficiently stirrable. Paraffins (EP-A-0 246 471) and free fatty acids (WO 94/26866) are known as such consistency regulators.
fatty acid esters as consistency regulators. According to the process described there, however, the consistency regulator is distilled as far as possible after the esterification reaction has ended and the end product is essentially free of fatty acid esters.
EP-A-0 262 420 also describes the use of fatty acid esters as consistency regulators, but in this case they can remain in the end product. Only fatty acid esters that come from alcohols with at least three carbon atoms are suitable as fatty acid esters.
the present invention relates to surfactant mixtures consisting essentially of acyloxyalkanesulfonate, fatty acid and fatty acid C 1 -C 2 alkyl ester, the content of fatty acid C 1 -C 2 alkyl ester in the surfactant mixture being 0.1 to 10% by weight, based on the content of acyloxyalkanesulfonate.
the acyloxyalkanesulfonates contained in the surfactant mixtures according to the invention preferably have the formula R 1 COOR 2 SO 3 M wherein R 1 is C 5 -C 31 alkyl or C 5 -C 31 alkenyl, R 2 C 2 -C 4 alkylene or C 2 -C 4 alkenylene, preferably C 2 alkylene, and M is an alkali metal, alkaline earth metal -, Ammonium or substituted ammonium ion means.
the alkyl and alkenyl groups R 1 can be straight-chain or branched.
the group R 1 CO is derived from fatty acids such as, for example, caproic acid, capric acid, lauric acid, myristic acid, stearic acid, arachic acid, oleic acid, linoleic acid, linolenic acid, coconut fatty acid and tallow fatty acid and mixtures thereof.
R 2 is preferably -CH 2 CH 2 -.
acyloxyalkanesulfonates are prepared by processes known per se by esterification of at least one fatty acid with at least one hydroxyalkanesulfonate (direct esterification). Such a method is described for example in EP-A-0 585 071 (US-A-5 384 421). An excess of fatty acid and the salt of the hydroxyalkanesulfonic acid are reacted in the presence of an esterification catalyst at a temperature of 180 to 240 ° C. with the simultaneous removal of water present.
the excess of free fatty acid is distilled off to a greater or lesser extent.
the coconut fatty acid has an unpleasant smell, so that it is necessary to remove the coconut fatty acid completely. It is therefore preferred to work in such a way that a second fatty acid, such as stearic acid, which has a higher boiling point than coconut fatty acid, is added after the reaction has ended. and then distills off the lower boiling unwanted free coconut fatty acid.
the presence of free fatty acid in the end product is desirable because the mixture of fatty acid and acyloxyalkanesulfonate has a better consistency and is easier to process than the acyloxyalkanesulfonate alone.
the amount of remaining fatty acid is generally 1 to 50 wt .-%, based on the content of acyloxyalkanesulfonate.
the addition of a second fatty acid can be dispensed with and the excess of free fatty acid is distilled practically completely from the reaction mixture in a thin-film evaporator at about 250 to 260 ° C. This is followed by the addition of the fatty acid C 1 -C 2 alkyl ester.
the fatty acid C 1 -C 2 alkyl esters are primarily the methyl esters; the fatty acid residue is essentially derived from fatty acids with C 5 -C 31 , preferably C 8 -C 16 alkenyl groups.
the amount of fatty acid alkyl ester is 0.1 to 10, preferably 0.5 to 5 wt .-%, based on the proportion of acyloxyalkanesulfonate.
the fatty acid alkyl ester is added by mixing the solid reaction product with the fatty acid alkyl ester in suitable mixing devices, for example in a kneader, until the mixture is homogeneous.
the fatty acid alkyl ester can also be added to the finished reaction product in the liquid melt, ie before cooling, or the already cooled product can be melted again and then mixed with the fatty acid alkyl ester. In the latter two cases, the final assembly is usually carried out using a scale roller or a cooling belt.
the reaction product that is obtained in the reaction of fatty acid and isethionate contains, depending on the respective production conditions usually about 50 to 99% by weight of acyloxyalkanesulfonate.
the rest consists essentially of free fatty acid.
the free fatty acid can also be almost completely distilled off from the reaction mixture and thus products which are essentially free of fatty acid are obtained.
the surfactant mixtures according to the invention obtained in this way are processed further in the customary manner to bar soaps.
SCID I and SCID II sodium cocoyl isethionate
basic soap 150 g of stearic acid
water 150 g of water
the same mixture of sodium cocoyl isethionate, basic soap, stearic acid and water was melted and the fatty acid alkyl ester was mixed in the melt, the percentage amounts of fatty acid alkyl ester given in the table below being based on the amount of sodium cocoyl isethionate (100%). In both cases the temperature was measured at which the melt could still be stirred.

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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)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

EP97108097A 1996-05-23 1997-05-20 Mélanges de surfactifs de sulphonates d'acyloxyalcanes et d'esters d'acides gras Withdrawn EP0814150A3 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE1996120748 DE19620748A1 (de)	1996-05-23	1996-05-23	Tensidmischungen aus Acyloxialkansulfonaten und Fettsäureester
DE19620748		1996-05-23

Publications (2)

Publication Number	Publication Date
EP0814150A2 true EP0814150A2 (fr)	1997-12-29
EP0814150A3 EP0814150A3 (fr)	1999-02-10

Family

ID=7795105

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP97108097A Withdrawn EP0814150A3 (fr)	1996-05-23	1997-05-20	Mélanges de surfactifs de sulphonates d'acyloxyalcanes et d'esters d'acides gras

Country Status (4)

Country	Link
EP (1)	EP0814150A3 (fr)
JP (1)	JPH1053793A (fr)
BR (1)	BR9703374A (fr)
DE (1)	DE19620748A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7659235B2 (en) *	2006-12-20	2010-02-09	Conopco, Inc.	Stable liquid cleansing compositions which may be prepared using fatty acyl isethionate surfactants
US7674759B2 (en) *	2007-09-05	2010-03-09	Conopco, Inc.	Stable liquid cleansing compositions containing high level of fatty acid isethionate surfactant products having more than 10 wt. % of fatty acid/fatty soap content
US7807612B2 (en) *	2007-12-18	2010-10-05	Conopco, Inc.	Fatty acyl isethionate product-containing liquid cleansing compositions stabilized with mixture of long chain and short chain fatty acids/fatty soaps

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1165608B (it) *	1978-01-19	1987-04-22	Unilever Nv	Barra detergente, particolarmente per lavaggio personale
DE3442579C2 (de) *	1984-11-22	1986-11-27	Akzo Gmbh, 5600 Wuppertal	Verfahren zur Herstellung von oberflächenaktiven Kondensationsprodukten
US5185101A (en) *	1991-08-15	1993-02-09	Dr. Gene, Inc.	Compositions containing salts of acyloxyalkanesulfonates
GB9310323D0 (en) *	1993-05-19	1993-06-30	Unilever Plc	Improvements relating to soap bars

1996
- 1996-05-23 DE DE1996120748 patent/DE19620748A1/de not_active Withdrawn
1997
- 1997-05-20 EP EP97108097A patent/EP0814150A3/fr not_active Withdrawn
- 1997-05-21 JP JP13093797A patent/JPH1053793A/ja not_active Withdrawn
- 1997-05-23 BR BR9703374A patent/BR9703374A/pt not_active Application Discontinuation

Also Published As

Publication number	Publication date
JPH1053793A (ja)	1998-02-24
BR9703374A (pt)	1998-09-15
DE19620748A1 (de)	1997-11-27
EP0814150A3 (fr)	1999-02-10

Legal Events

Date	Code	Title	Description
1997-11-07	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1997-12-29	AK	Designated contracting states	Kind code of ref document: A2 Designated state(s): AT BE CH DE DK ES FR GB IT LI LU NL PT SE
1998-12-23	PUAL	Search report despatched	Free format text: ORIGINAL CODE: 0009013
1999-02-10	AK	Designated contracting states	Kind code of ref document: A3 Designated state(s): AT BE CH DE DK ES FR GB IT LI LU NL PT SE
1999-03-19	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN
1999-05-06	18W	Application withdrawn	Withdrawal date: 19990309

Publication	Publication Date	Title
EP0302329B1 (fr)	1992-01-29	Préparation de bétaines en solution aqueuse concentrée fluide
DE69105520T2 (de)	1995-06-08	Phase-transfer-verfahren für glucamiddetergentien.
EP0613457B1 (fr)	1996-06-19	Esters d'acides gras avec polyols ethoxyles
DE2546716A1 (de)	1976-04-29	Verfahren zum herstellen eines oberflaechenaktiven produktes
DE69027495T2 (de)	1996-11-28	Weichmacher für Gewebe
DE69209709T2 (de)	1996-10-24	Verfahren zur Herstellung von aus Di- oder Tri-Carboxylsäuren abgeleiteten Grenzflächenaktiven Mitteln
EP0182017B1 (fr)	1989-03-29	Produits de condensation tensio-actifs
WO1997031888A1 (fr)	1997-09-04	Composes quaternaires d'ester a faible point de fusion
EP0452349B1 (fr)	1994-06-01	Procede de production de derives d'imidazoline amphoteres tensio-actifs
EP0391392B1 (fr)	1995-07-26	Compositions aqueuses détergentes peu moussantes et stables au froid comprenant des agents tensioactifs non ioniques, anioniques et cationiques et leur application
EP0814150A2 (fr)	1997-12-29	Mélanges de surfactifs de sulphonates d'acyloxyalcanes et d'esters d'acides gras
DE2820035C3 (de)	1980-09-11	Feinwaschmittel
EP0370273A1 (fr)	1990-05-30	Mélanges d'alcools gras et leurs éthoxylates à caractéristiques modifiées à basse température
EP0739878B2 (fr)	2002-07-03	Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine
EP0518881B1 (fr)	1994-12-28	Procede de sulfonation de melanges contenant des glucosides d'alkyle
EP0298326B1 (fr)	1992-12-16	Procédé de production de 1-(alcylaminoalkyl)-2-imidazolines substituées en position 2
EP0674701B1 (fr)	1997-06-18	Dispersions aqueuses d'adoucissants pour textiles
DE2817626C2 (fr)	1987-05-27
DE2225793B2 (de)	1979-06-21	Verfahren zur kontinuierlichen Herstellung einer Mischung von primären und sekundären Phosphatestern von organischen Hydroxyverbindungen
DE69004035T2 (de)	1994-03-31	Verfahren zur Herstellung von Kohlensäureestern.
DE19622981A1 (de)	1997-12-11	Säure-Addukte von Fettsäurepolyhydroxyalkylamiden
EP0834547A2 (fr)	1998-04-08	Mélanges de tensioactifs contenant des sulfonates d'acyloxyalcanes
EP0735021A2 (fr)	1996-10-02	Procédé pour la préparation d'acyloxyalcanesulfonates
EP0834545A2 (fr)	1998-04-08	Mélanges de tensioactifs contenant des sulfonates d'acyloxyalcanes
DE3725935A1 (de)	1988-03-24	Oberflaechenaktive kondensationsprodukte