EP0780464A2 - Procédé pour la préparation des concentrés d'agents tensio-actifs de couleur claire à basse viscosité - Google Patents

Procédé pour la préparation des concentrés d'agents tensio-actifs de couleur claire à basse viscosité Download PDF

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Publication number
EP0780464A2
EP0780464A2 EP96119947A EP96119947A EP0780464A2 EP 0780464 A2 EP0780464 A2 EP 0780464A2 EP 96119947 A EP96119947 A EP 96119947A EP 96119947 A EP96119947 A EP 96119947A EP 0780464 A2 EP0780464 A2 EP 0780464A2
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EP
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Prior art keywords
alkyl
carbon atoms
acid
process according
concentrates
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.)
Granted
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EP96119947A
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German (de)
English (en)
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EP0780464B1 (fr
EP0780464A3 (fr
Inventor
Michael Dr. Neuss
Karl Heinz Dr. Schmid
Andrea Bornträger
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BASF Personal Care and Nutrition GmbH
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Henkel AG and Co KGaA
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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
    • C11D1/88—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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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 a process for producing light-colored, low-viscosity surfactant concentrates by mixing sugar surfactants and betaines in the gel phase.
  • Alkyl oligoglycosides in particular alkyl oligoglucosides, are nonionic surfactants which are becoming increasingly important due to their excellent detergent properties and high ecotoxicological compatibility.
  • the manufacture and use of these substances have recently been described in a number of review articles, of which the publications by H.Hensen in Skin Care Forum, 1, (Oct. 1992), D. Balzer and N. Ripke in Soap Oils are representative -Fette-waxes 118 , 894 (1992) and B.Brancq in soap-oils-fat waxes 118 , 905 (1992) should be mentioned.
  • advantageous properties are known from a second group of sugar surfactants, the fatty acid N-alkylpolyhydroxyalkylamides, in particular the fatty acid N-alkylglucamides.
  • sugar surfactants are problematic.
  • no pumpable aqueous concentrates with a solids content above 40% by weight can be produced without the sugar component being partially decomposed in the course of the concentration.
  • the glycosides and glucamides have this property in common with most anionic surfactants, which form a viscous gel phase above an active substance content of about 35% by weight.
  • the Sugar surfactants also tend to crystallize during storage at low temperatures, which makes their further use significantly more difficult.
  • EP-A 0 250 181 (Helene Curtis) relates to liquid detergents containing alkyl glucosides, anionic surfactants and selected amphoteric surfactants with a betaine structure.
  • EP-A 0 341 071 (Unilever) discloses surfactant combinations containing alkyl glucosides, alkyl sulfates, betaines and / or amine oxides and optionally alkanolamides.
  • fatty acid N-alkylpolyhydroxyalkylamides are also the subject of a large number of publications. Their use as a thickener is known, for example, from European patent application EP-A1 0 285 768 (Hüls). French published patent application FR-A 1 580 491 (Henkel) describes aqueous detergent mixtures based on sulfates and / or sulfonates, nonionic surfactants and, if appropriate, soaps, which contain fatty acid N-alkylglucamides as foam regulators. Mixtures of short- and long-chain glucamides are described in German Patent DE-C1 44 00 632 (Henkel) described.
  • German published applications DE-A1 42 36 958 and DE-A1 43 09 567 also report on the use of glucamides with longer alkyl residues than pseudoceramides in skin care products and on combinations of glucamides with protein hydrolyzates and cationic surfactants in hair care products.
  • the surfactant concentrates represent a particularly advantageous form of trade for manufacturers and users, since they have been minimized in terms of their water content and thus cause lower costs for transport and storage. Nevertheless, it is desirable that the surfactant concentrates, when used in the final formulations, which are naturally highly diluted and have a solids content of 20 to 30% by weight, have a sufficiently high viscosity or can be thickened easily using known additives.
  • the complex object of the invention was therefore to provide light-colored, pumpable aqueous surfactant concentrates with good skin-cosmetic compatibility based on alkyl glycosides or fatty acid glucamides and betaines, which are characterized by high storage stability, a Brookfield viscosity of at most 10,000 mPas and have a solids content of 40 to 60% by weight.
  • Alkyl and alkenyl oligoglycosides are known nonionic surfactants which follow the formula (I) in which R 1 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 1 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 1 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.
  • Fatty acid N-alkylpolyhydroxyalkylamides are nonionic surfactants which follow the formula (II) in the R 2 CO for an aliphatic acyl radical having 6 to 22 carbon atoms, R 3 for hydrogen, an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms and [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 12 carbon atoms and 3 to 10 hydroxyl groups stands.
  • the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • a reducing sugar with ammonia
  • an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • the fatty acid N-alkylpolyhydroxyalkylarnides are preferably derived from reducing sugars with 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (III) :
  • R 3 is preferably used as the fatty acid N-alkyl polyhydroxyalkyl amide.
  • I hydrogen or an alkyl group and R 2 CO represents the acyl radical of 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, arachic acid, gadoleic acid or behenic acid, behenic acid whose technical mixtures are available.
  • Fatty acid N-alkyl glucamides of the formula (III) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C 12/14 coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • 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 (IV) in which R 4 for alkyl and / or alkenyl radicals with 6 to 22 carbon atoms, R 5 for hydrogen or alkyl radicals with 1 to 4 carbon atoms, R 6 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 4 for alkyl and / or alkenyl radicals with 6 to 22 carbon atoms
  • R 5 for hydrogen or alkyl radicals with 1 to 4 carbon atoms
  • R 6 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.
  • Carboxyalkylation products of amidoamines which follow the formula (V) are also suitable , in which R 7 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 and R 5 , R 6 , 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 (VI) in which R 8 is an alkyl radical having 5 to 21 carbon atoms, R 9 is a hydroxyl group, an OCOR 8 or NHCOR 8 radical and m is 2 or 3.
  • R 8 is an alkyl radical having 5 to 21 carbon atoms
  • R 9 is a hydroxyl group
  • an OCOR 8 or NHCOR 8 radical 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
  • the preparation of the surfactant concentrate is based on highly concentrated aqueous starting materials in the gel form.
  • This means that the alkyl and / or alkenyl oligoglycosides and / or the fatty acid N-alkylpolyhydroxyalkylamides are used in the form of aqueous gels with a sugar surfactant content in the range from 45 to 60 and preferably 45 to 55% by weight.
  • the betaine surfactants are generally used with a non-aqueous content in the range from 45 to 60, preferably 48 to 54% by weight and a betaine content in the range from 25 to 40, preferably 28 to 35% by weight.
  • the surfactant concentrates are produced in a purely mechanical way by mixing the gel-like starting materials, if appropriate at elevated temperature and strong shear.
  • the betaines are reacted in a known manner, for example by reacting suitable tertiary amines with aqueous sodium chloroacetate solution at about 90 ° C., and the crude betaines are mixed with the aqueous glucoside or glucamide pastes without cooling.
  • the betainization is carried out with just the amount of water as solvent that the desired solids content is obtained in the mixed product with the sugar surfactants. In sum, this means that the betainization can be performed with an unusually low amount of solvent.
  • the surfactant concentrates can contain small amounts, ie 0.5 to 3 and preferably 1 to 2% by weight, based on the concentrates, of free fatty acids.
  • Typical examples are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and technical mixtures thereof , which occur, for example, in the pressure splitting of natural fats and oils, in the reduction of aldehydes from Roelen's oxosynthesis or in the dimerization of unsaturated fatty acids.
  • the surfactant concentrates according to the invention are distinguished by a low viscosity and yield point. They are light colored, color and storage stable. They are therefore suitable for the production of a large number of surface-active agents, such as, for example, washing, rinsing and cleaning agents, in which they are present in amounts of 0.5 to 50 and preferably 2 to 35% by weight, based on the agent can.
  • surfactant ingredients were mixed at 40 ° C., resulting in surfactant concentrates of the composition shown in Table 2: Table 2 Surfactant concentrates composition example 1 Example 2 Example 3 Alkyl oligoglucoside 50 60 50 Betaine 1 50 - - Betaine 2 - 40 - Betaine 3 - - 50 Solids content mixture 54 52 40 Consistency (25 ° C) thin paste thin paste thin paste Color number (Gardner) 1 1 1

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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)
  • Cosmetics (AREA)
EP96119947A 1995-12-21 1996-12-12 Procédé pour la préparation de concentrés en tensio-actifs, de couleur claire à basse viscosité Expired - Lifetime EP0780464B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19548068 1995-12-21
DE19548068A DE19548068C1 (de) 1995-12-21 1995-12-21 Verfahren zur Herstellung hellfarbiger, niedrigviskoser Tensidkonzentrate

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EP0780464A2 true EP0780464A2 (fr) 1997-06-25
EP0780464A3 EP0780464A3 (fr) 1998-12-02
EP0780464B1 EP0780464B1 (fr) 2003-04-16

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000042141A1 (fr) * 1999-01-14 2000-07-20 Cognis Deutschland Gmbh Procede pour inhiber la cristallisation de concentres tensioactifs
WO2013178700A2 (fr) 2012-05-30 2013-12-05 Clariant International Ltd. Composition contenant de la n-méthyl-n-acylglucamine
US10675231B2 (en) 2017-02-17 2020-06-09 The Procter & Gamble Company Packaged personal cleansing product
US10806686B2 (en) 2017-02-17 2020-10-20 The Procter And Gamble Company Packaged personal cleansing product
US11179301B2 (en) 2016-10-21 2021-11-23 The Procter And Gamble Company Skin cleansing compositions and methods
US11185486B2 (en) 2016-10-21 2021-11-30 The Procter And Gamble Company Personal cleansing compositions and methods

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DE10037405A1 (de) * 2000-08-01 2002-02-21 Henkel Ecolab Gmbh & Co Ohg Reinigung harter Oberflächen mit verdickenden wäßrigen Reinigungsmitteln
MX369415B (es) 2015-04-23 2019-11-07 Procter & Gamble Composiciones de limpieza personal concentradas.
WO2016172482A1 (fr) 2015-04-23 2016-10-27 The Procter & Gamble Company Compositions concentrées de nettoyage personnel et procédés correspondants
MX371306B (es) 2015-04-23 2020-01-24 Procter & Gamble Composiciones concentradas para la limpieza personal y usos.
CN107530249B (zh) 2015-04-23 2021-09-07 宝洁公司 浓缩型个人清洁组合物及方法

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US2703798A (en) 1950-05-25 1955-03-08 Commercial Solvents Corp Detergents from nu-monoalkyl-glucamines
FR1580491A (fr) 1967-07-19 1969-09-05
EP0075994A2 (fr) 1981-09-28 1983-04-06 THE PROCTER & GAMBLE COMPANY Compositions détergentes contenant un mélange d'alkylpolysaccharide, d'agents tensio-actifs d'oxydes d'amine et de savon d'acides gras
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WO2000042141A1 (fr) * 1999-01-14 2000-07-20 Cognis Deutschland Gmbh Procede pour inhiber la cristallisation de concentres tensioactifs
WO2013178700A2 (fr) 2012-05-30 2013-12-05 Clariant International Ltd. Composition contenant de la n-méthyl-n-acylglucamine
US11179301B2 (en) 2016-10-21 2021-11-23 The Procter And Gamble Company Skin cleansing compositions and methods
US11185486B2 (en) 2016-10-21 2021-11-30 The Procter And Gamble Company Personal cleansing compositions and methods
US10675231B2 (en) 2017-02-17 2020-06-09 The Procter & Gamble Company Packaged personal cleansing product
US10806686B2 (en) 2017-02-17 2020-10-20 The Procter And Gamble Company Packaged personal cleansing product
US11202744B2 (en) 2017-02-17 2021-12-21 The Procter And Gamble Company Packaged personal cleansing product

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EP0780464B1 (fr) 2003-04-16
DE59610348D1 (de) 2003-05-22
EP0780464A3 (fr) 1998-12-02
DE19548068C1 (de) 1997-06-19

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