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WO1996025389A1 - Concentres aqueux de faible viscosite d'agents tensio-actifs de betaïne - Google Patents

Concentres aqueux de faible viscosite d'agents tensio-actifs de betaïne Download PDF

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Publication number
WO1996025389A1
WO1996025389A1 PCT/EP1996/000520 EP9600520W WO9625389A1 WO 1996025389 A1 WO1996025389 A1 WO 1996025389A1 EP 9600520 W EP9600520 W EP 9600520W WO 9625389 A1 WO9625389 A1 WO 9625389A1
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WO
WIPO (PCT)
Prior art keywords
concentrates
carbon atoms
formula
range
independently
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.)
Ceased
Application number
PCT/EP1996/000520
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German (de)
English (en)
Inventor
Massimo Armada
Ansgar Behler
Joaquim Bigorra Llosas
Hermann Hensen
Rafael Pi Subirana
Werner Seipel
Holger Tesmann
Günter Uphues
Karl-Heinz Schmid
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 WO1996025389A1 publication Critical patent/WO1996025389A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/18—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
    • 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
    • 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
    • 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
    • C11D1/92—Sulfobetaines ; Sulfitobetaines

Definitions

  • the invention relates to low-viscosity aqueous concentrates of betaine surfactants containing selected nitrogen compounds, a process for their preparation and the use of the nitrogen compounds as liquefying agents for aqueous betaine concentrates.
  • Betaines or amphoteric surfactants are extremely skin-friendly and have excellent cleansing properties. They are therefore particularly suitable for the assembly of a large number of surface-active products.
  • their preparation is based on tertiary amines which are reacted with sodium chloroacetate to form alkyl betaines.
  • the reaction of fatty acid aminoamides or imidazolines with sodium chloroacetate leads to the formation of amphoteric surfactants of the glycinate type; If acrylic acid ester is used as the alkylating agent, aminopropionates are formed.
  • Compounds of the type mentioned are in one Peru of reviews described, of which only Parf.Co8m.Arom. -, 67 (1986), HAPPI, 70, (Nov. 1986) and Soap Cosm.Chem.Spec. 46, (Apr. 1990).
  • a particular concern in the production of betaines or amphoteric surfactants is to provide products that are as pure as possible and thus dermatologically and toxicologically safe. For example, traces of free amines, chloroacetic acid and especially dichloroacetic acid in the surfactants are undesirable. Preservatives which are intended to protect betaines or amphoteric surfactants from microbial attack are also often not desired, so that there is a further need for products which are stabilized against bacterial attack even without the addition of auxiliaries.
  • a third object of the invention is to provide as light-colored products as possible with a high solids content, preferably in the range from 40 to 60% by weight.
  • DE-Al 39 39 264 proposes to reduce the chloroacetic acid content in amphoteric surfactants by subsequently treating the aqueous solutions with ammonia, amino acids or oligopeptides.
  • a process is known from DE-0S 29 26 479 (Th.Goldschmidt) in which the quaternization is carried out in the pH range from 7.5 to 10.5 and the residual content is thus determined free alkylating agent minimized.
  • the teaching of DE-A 20 63 424 (Rewo), which describes the pH regulation for the alkylation of imidazolines, points in the same direction.
  • DE-C 37 26 322 (Th.Goldschmidt) describes a process for the aftertreatment of betaines, in which mineral acids are added to the substances in amounts such that the pH of the solution is 1 to 4.5.
  • these processes have no influence on the dichloroacetic acid content.
  • DE-Al 42 05 880 (Th.Goldschmidt) it is proposed to minimize chlorinated impurities that the betaines are carried out in aqueous solution at a temperature in the range from 115 to 180 ° C. and thus under increased pressure.
  • DE-Cl 42 07 386 discloses betaine concentrates with solids contents above 40% by weight, which contain 1 to 3% by weight of free fatty acid and 0 to 4% by weight.
  • % Contain glycerol have a free amidoamine content of less than 1% by weight and have a pH in the range from 5 to 8.
  • the object of the invention was to provide new aqueous betaines which are flowable and pumpable, even when stored for a long time gel, have a solids content of at least 40% by weight and a minimized content of undesired secondary components, in particular chlorinated substances and free amines.
  • the invention relates to low-viscosity aqueous concentrates of betaine surfactants of the formula (I),
  • R 1 is an aliphatic alkyl radical with 8 to 22 carbon atoms
  • R ⁇ and R ⁇ independently of one another for an alkyl and / or hydroxyalkyl radical with 1 to 4 carbon atoms
  • n and m independently of one another for numbers in the range from 1 to 5 and p stands for 0 or 1, obtainable by condensation of fatty amines or fatty acid aminoamides with halogenated carboxylic acid salts, which are characterized in that they contain a nitrogen compound selected from the group formed by
  • the addition of the nitrogen compounds mentioned reduces the viscosity of the concentration to such an extent that flowable and pumpable products Products with a solids content in the range of 40 to 55 wt .-% can be made available, which show no tendency to gelation even after prolonged storage.
  • the concentrates according to the invention are also light colored and have a minimized content of chlorinated compounds. A free aminoamide content is not necessary to ensure a sufficiently low viscosity.
  • the concentrates are sufficiently protected against antimicrobial attack without the addition of preservatives.
  • Betaines more precisely fatty alkyl betaines and fatty acid amido betaines, are both known groups of substances.
  • the invention preferably relates to
  • R 1 is an alkyl radical having 8 to 18 carbon atoms
  • R2 and R3 are each a methyl group
  • n and m independently of one another are 1, 2 or 3 and p is 0, respectively.
  • Sulfobetaines are known amphoteric surfactants which can be obtained by quaternizing fatty amines or fatty acid aminoamides, preferably with chloroalkanesulfonates such as, for example, chlorohydroxypropanesulfonic acid; the latter in turn is accessible by reacting epichlorohydrin with sodium bisulfite.
  • chloroalkanesulfonates such as, for example, chlorohydroxypropanesulfonic acid
  • Sulfobetaines which are suitable as liquefying agents of group (a) follow, for example, the formula (II),
  • R ⁇ represents an aliphatic alkyl radical with 8 to 22, preferably 8 to 18 carbon atoms
  • R ⁇ and R *> independently of one another for an alkyl and / or hydroxyalkyl radical having 1 to 4 carbon atoms
  • pl is 0 or 1
  • A is an optionally hydroxy-substituted alkylene group having 1 to 5 carbon atoms.
  • Typical examples are quaternization products from coconut dimethylamine or coconut fatty acid amidopropylamine with chlorohydroxy propane sulfonic acid or its sodium salt.
  • Amphoglycinates which can be used as liquefying agents in group (b) follow the formulas (purple) and (Illb),
  • R 7 stands for an aliphatic alkyl radical having 8 to 22, preferably 8 to 18 carbon atoms, n2 and m2 independently of one another for numbers in the range from 1 to 5, p2 for 0 or 1 and X for an alkali metal.
  • Particularly suitable amphoglycinates are derived from coconut ethanolamine or coconut fatty acid ethyl ethanol amide.
  • the corresponding imidazoline precursors can also be added to the betaines according to the invention before or during the quaternization. In the course of this embodiment, the amphoglycinates are generated in situ and liquefy the product.
  • Dicarboxylic acid mono- and / or diamides are suitable as fluidizing agents in group (c). These are preferably reaction products of dicarboxylic acids of the formula (IV) HOOC- [A] -COOH (IV)
  • A represents a linear or branched, aliphatic, cycloaliphatic or aromatic alkylene group having 1 to 36 carbon atoms, with amines of the formula (V)
  • R ⁇ represents a linear or branched, aliphatic, cycloaliphatic, optionally hydroxy-substituted and / or amino-substituted alkyl radical having 1 to 18, preferably 2 to 4 carbon atoms and R ⁇ represents hydrogen or R 8 .
  • Typical examples are reaction products of succinic acid, maleic acid, adipic acid, phthalic acid and / or dimer fatty acid with ethylamine, ethanolamine, propanolamine, diethanolamine and especially dimethylaminopropylamine.
  • the latter is preferably added before or during quaternization and betainized in situ.
  • Reaction products of dimer fatty acid with dimethylaminopropylamine or adipic acid with diethylenetriamine are particularly preferred.
  • the betaine concentrates according to the invention have a solids content of at least 40, preferably from 40 to 60 and in particular from 42 to 48% by weight, based on the concentrates.
  • the active substance content ie the content of betaines, is generally 8 to 12% by weight lower.
  • the nitrogen compounds in the concentrates can be 1 to 40, preferably 2 to 25 and in particular 4 to 8% by weight, based on the concentrates.
  • the proportion of inorganic salts, for example sodium chloride, can make up 5 to 10% by weight.
  • the content of free fatty acid amino amide and soap is usually less than 1 and in particular less than 0.8% by weight, the content of mono- and dichloroacetic acid in each case less than 5 ppm - based on the concentrates.
  • the betaine concentrates can contain 0.1 to 0.8% by weight of free C 1 -C 2 -fatty acid and / or 0.1 to 3% by weight of a polyol, preferably glycerin, sorbitol or butyl glucoside can be added.
  • the invention further relates to a process for the preparation of low-viscosity aqueous concentrates of betaine surfactants, in which fatty amines or fatty acid aminoamides are reacted with halocarboxylic acids or their salts in a manner known per se, and nitrogen compounds selected from the group which is formed of
  • aqueous betaines according to the invention are also highly concentrated, liquid, stable in storage and have a minimized proportion of undesirable secondary constituents. They are suitable for the production of surface-active agents, especially cleaning products as well as hair treatment and care products. agents in which they can be present in amounts of 1 to 30, preferably 2 to 10% by weight, based on the agents.
  • Another object of the invention therefore relates to the use of the nitrogen compounds mentioned as a liquefier for the preparation of low-viscosity aqueous concentrates of betaine surfactants.
  • Example 1 was repeated in place of the sulfobetaine using 200 g of an amphoglycinate based on coconut fatty acid aminoethylamide (40% by weight AS). The characteristics of the low-viscosity product are summarized in Table 1.
  • Example 1 was repeated in place of the sulfobetaine using 40 g trimethylglycine (100 wt% AS). The characteristics of the low-viscosity product are summarized in Table 1.
  • Example 1 was repeated instead of the sulfobetaine using 40 g of a monoamide of a technical dimer fatty acid with dimethylaminopropylamine (100% by weight AS).
  • the characteristics of the low-viscosity product are summarized in Table 1.
  • Example 1 was repeated without adding a nitrogen compound.
  • the characteristics of the product are summarized in Table 1.
  • FFS free fatty acid
  • GLY glycerin

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des concentrés aqueux de faible viscosité d'agents tensio-actifs de bétaïne, de formule (I), dans laquelle R1 désigne un reste alkyle aliphatique comportant 8 à 22 atomes de carbone, R2 et R3 désignent, indépendamment l'un de l'autre, un reste alkyle et/ou hydroxyalkyle de 1 à 4 atomes de carbone, n et m présentent, indépendamment de l'autre, des valeurs comprises entre 1 et 5, et p est égal à 0 ou à 1. On obtient ces concentrés en faisant réagir des amines grasses ou des aminoamides d'acides gras, avec des acides carboxyliques halogénés ou leurs sels, de façon connue, et en ajoutant avant, pendant ou après la quaternisation, des composés azotés, choisis dans le groupe comprenant (a) les sulfobétaïnes, (b) les amphoglycinates, (c) la triméthylglycine et/ou (d) les monoamides et/ou les diamides d'acides dicarboxyliques, et servant d'agent de liquéfaction..
PCT/EP1996/000520 1995-02-16 1996-02-08 Concentres aqueux de faible viscosite d'agents tensio-actifs de betaïne Ceased WO1996025389A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19505196.3 1995-02-16
DE19505196A DE19505196C1 (de) 1995-02-16 1995-02-16 Niedrigviskose wäßrige Konzentrate von Betaintensiden

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WO1996025389A1 true WO1996025389A1 (fr) 1996-08-22

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DE (1) DE19505196C1 (fr)
WO (1) WO1996025389A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0739878B1 (fr) * 1995-04-29 1998-06-10 Witco Surfactants GmbH Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine
US6830755B2 (en) 1999-10-01 2004-12-14 Johnson & Johnson Consumer Companies, Inc. Method for relaxing human beings using personal care compositions
EP1516915A1 (fr) * 2003-09-22 2005-03-23 Clariant GmbH Solutions aqueuses concentrées de tensioactifs amphotères
US6986747B2 (en) 2002-01-29 2006-01-17 Johnson & Johnson Consumer Companies Method of measuring the stress or relaxation level of a mammal
CN109499773A (zh) * 2019-01-17 2019-03-22 湖南中医药大学 酰氨基多元羧酸/羟肟酸类化合物在矿物浮选中应用

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2126495B1 (es) 1996-11-05 1999-12-01 Kao Corp Sa Composiciones acuosas concentradas de tensioactivos del tipo de las betainas y su procedimiento de obtencion.
IT1317863B1 (it) * 2000-02-29 2003-07-15 Vama Farmacosmetica S R L Fabbricazione e utilizzo di amfoglicinati da oli e burri vegetali.
DE10207924A1 (de) * 2002-02-23 2003-09-04 Clariant Gmbh Hochkonzentrierte wässrige Lösungen von Betainen oder Aminoxiden
DE102004055549A1 (de) 2004-11-17 2006-05-18 Goldschmidt Gmbh Verfahren zur Herstellung hochkonzentrierter fließfähiger wässriger Lösungen von Betainen
CN104981286B (zh) * 2013-02-11 2017-06-23 禾大公司 分散剂
CN117105804B (zh) * 2023-08-23 2025-08-15 赞宇科技集团股份有限公司 一种甜菜碱型表面活性剂的生产方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0353580A2 (fr) * 1988-08-05 1990-02-07 Th. Goldschmidt AG Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine
DE4207386C1 (fr) * 1992-03-09 1993-08-05 Th. Goldschmidt Ag, 4300 Essen, De
DE4227391C1 (de) * 1992-08-19 1993-09-30 Goldschmidt Ag Th Wäßrige Zubereitungen, die Betaine auf Basis polymerer Fettsäuren enthalten
DE4240154A1 (de) * 1992-11-30 1994-06-01 Henkel Kgaa Verfahren zur Herstellung dünnflüssiger, lagerstabiler Amphotenside
EP0647613A2 (fr) * 1993-10-08 1995-04-12 Witco Surfactants GmbH Procédé pour la préparation de dispersions aqueuses de bétaines fortement concentrées et fluides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0353580A2 (fr) * 1988-08-05 1990-02-07 Th. Goldschmidt AG Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine
DE4207386C1 (fr) * 1992-03-09 1993-08-05 Th. Goldschmidt Ag, 4300 Essen, De
DE4227391C1 (de) * 1992-08-19 1993-09-30 Goldschmidt Ag Th Wäßrige Zubereitungen, die Betaine auf Basis polymerer Fettsäuren enthalten
DE4240154A1 (de) * 1992-11-30 1994-06-01 Henkel Kgaa Verfahren zur Herstellung dünnflüssiger, lagerstabiler Amphotenside
EP0647613A2 (fr) * 1993-10-08 1995-04-12 Witco Surfactants GmbH Procédé pour la préparation de dispersions aqueuses de bétaines fortement concentrées et fluides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0739878B1 (fr) * 1995-04-29 1998-06-10 Witco Surfactants GmbH Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine
US6830755B2 (en) 1999-10-01 2004-12-14 Johnson & Johnson Consumer Companies, Inc. Method for relaxing human beings using personal care compositions
US6986747B2 (en) 2002-01-29 2006-01-17 Johnson & Johnson Consumer Companies Method of measuring the stress or relaxation level of a mammal
EP1516915A1 (fr) * 2003-09-22 2005-03-23 Clariant GmbH Solutions aqueuses concentrées de tensioactifs amphotères
CN109499773A (zh) * 2019-01-17 2019-03-22 湖南中医药大学 酰氨基多元羧酸/羟肟酸类化合物在矿物浮选中应用

Also Published As

Publication number Publication date
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