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WO1994021771A1 - Melanges de detergents - Google Patents

Melanges de detergents Download PDF

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Publication number
WO1994021771A1
WO1994021771A1 PCT/EP1994/000807 EP9400807W WO9421771A1 WO 1994021771 A1 WO1994021771 A1 WO 1994021771A1 EP 9400807 W EP9400807 W EP 9400807W WO 9421771 A1 WO9421771 A1 WO 9421771A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
alkyl
radical
fatty acid
acid amides
Prior art date
Application number
PCT/EP1994/000807
Other languages
German (de)
English (en)
Inventor
Hermann Hensen
Holger Tesmann
Jörg KAHRE
Reinhard Müller
Wolfhard Scholz
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to JP6520634A priority Critical patent/JPH08508055A/ja
Priority to EP94911890A priority patent/EP0690907A1/fr
Publication of WO1994021771A1 publication Critical patent/WO1994021771A1/fr

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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • 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
    • A61K8/42—Amides
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/645—Proteins of vegetable origin; Derivatives or degradation products thereof
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • C11D1/645—Mixtures of compounds all of which are cationic
    • 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
    • C11D1/526—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
    • 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
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • the invention relates to detergent mixtures containing polyhydroxyfatty acid amides, protein hydrolyzates and optionally monomeric cationic surfactants, a process for improving the bounce of hair, in which the detergent mixtures are used, hair fixatives which contain the detergent mixtures and their use for the preparation of hair fixatives.
  • Washed hair is difficult and reluctant to style due to the degreasing and removal of all dirt particles.
  • the electrostatic charging of the hair makes it difficult to create a durable hairstyle and to maintain it. It depends on the quality of the shapo and the level of ambient humidity and is particularly noticeable in winter when the heating air is warm and dry. To improve the combability of washed and terry hair, for conditioning and hair stabilizers are therefore used to stabilize them against external influences.
  • the object of the invention was therefore to develop new hair fixatives with well dermatologically compatible and easily biodegradable film formers. Another task was to provide products that have improved rinsability or brushability. Description of the invention
  • the invention relates to detergent mixtures containing
  • R ⁇ -CO for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R ⁇ for hydrogen, an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms
  • [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 10 carbon atoms and 3 is up to 10 hydroxyl groups
  • detergent mixtures containing polyhydroxy fatty acid amides, protein hydrolyzates and optionally cationic surfactants are able to improve the bounce of hair in a way that has not been possible to date using conventional mixtures of polymers and cationic surfactants.
  • the products are easy to wash out, brush out easily and are characterized by excellent dermatological and ecological Tolerance out.
  • the invention also includes the knowledge that mixtures of polyhydroxy fatty acid amides and protein hydrolyzates can act as film formers, a property that is otherwise only known from highly polymeric systems.
  • the polyhydroxy fatty acid amides 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
  • subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • the detergent mixtures according to the invention preferably contain polyhydroxy fatty acid amides of the formula (I) in which R ⁇ -CO represents an acyl radical having 12 to 22 carbon atoms, R 2 represents hydrogen or a methyl group, and [Z] represents a reduced glucose radical.
  • the preferred polyhydroxy fatty acid amides are therefore fatty acid N-alkylglucamides, as represented by the formula (II): R 2 OH OH OH
  • the polyhydroxy fatty acid amides used are preferably fatty acid-N-alkylglucamides of the formula (II) in which R 2 represents hydrogen or a methyl group and R * CO represents the acyl residue of lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, Elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachidic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
  • R 2 represents hydrogen or a methyl group
  • R * CO represents the acyl residue of lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, Elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachidic acid, gadoleic acid, be
  • fatty acid N-alkylglucamides of the formula (II) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or Ci2 / i4 coconut fatty acid Dzw «a corresponding derivative.
  • Protein hydrolyzates are substances which are usually produced by breaking down animal protein, preferably bovine collagen. In alkaline hydrolysis there is an unspecific opening of the peptide bonds, which follows the rules of statistics. Since the carboxy groups of the peptides are present as a salt during the hydrolysis, while the amino groups are unprotected and can be split off in part, a hydrolyzate results in which the polypeptides have a higher number of carboxy than amino groups. Also the acidic hydrolysis leads to unspecific opening of the peptide bonds. In contrast to alkaline hydrolysis, in the acidic degradation, however, the amino groups are in the form of salts and the carboxy groups are in free form, but these have a considerably higher stability than the unprotected amino groups. Depending on the hydrolysis process, the products therefore show strong structural differences [cf. YES . Oil. Chem. Soc., J59, 217 (1982); Soap-Oil-Fat-Waxes 108, 177 (1982)].
  • the average molecular weight can be set via the reaction conditions and - as with the alkaline or acidic hydrolysates - can be in the range from 1,000 to 10,000, preferably 2,000 to 6,000.
  • protein hydrolysates which are obtained by enzymatic degradation of vegetable protein are preferably used. Typical examples are hydrolyzates of soy protein, almond protein, wheat protein and / or potato protein. Compared to animal products, the protein hydrolysates mentioned also have the advantage of improved dermatological tolerance.
  • the detergent mixtures can the polyhydroxy fatty acid amides and the protein hydrolyzates in a weight ratio of 1: 5 to 5 : 1, preferably 1: 3 to 3: 1 - based on the mixtures.
  • Suitable monomeric cationic surfactants are, for example, quaternary ammonium compounds (QAC) of the formula (III)
  • R ⁇ for an optionally hydroxy-substituted alkyl and / or alkenyl radical having 6 to 22 carbon atoms R ⁇ for R3 or an alkyl radical with 1 to 5 carbon atoms and R5 and R *> independently of one another for alkyl radicals with 1 to 5 carbon atoms and X represents halogen, phosphate, alkyl sulfate or alkyl phosphate.
  • the QAC are known substances that can be obtained using the relevant methods of preparative organic chemistry.
  • One method for their preparation is, for example, to guaternate tertiary amines with methyl chloride or dimethyl sulfate.
  • QACs suitable for the purposes of the invention are stearyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride (Dehyquart ( R ) A, Henkel), dicetyldimethylammonium chloride, 2-hydroxycetyl-2-hydroxyethyldimethylammonium chloride (Dehyquart ( R ) E, Hen ⁇ kel) or oxyethylammonium phosphate (Dehyquart ( R ) SP, Henkel).
  • QAVs are preferably used in which R 3 is for one optionally hydroxy-substituted alkyl radical with 16 to 18 carbon atoms, R 4 for R 3 , a methyl or hydroxyethyl group, R ⁇ and R *> for a methyl group and X for chloride or methyl sulfate.
  • R 7 CO for an aliphatic, optionally hydroxy-substituted acyl radical having 12 to 22 carbon atoms and 0 or 1 double bond
  • R ⁇ for a methyl group or a polyethylene glycol ether chain with 1 to 5 ethylene oxide units
  • x, y and z for 0 or in Sum of numbers from 1 to 5 and Y stands for halogen, alkyl sulfate or alkyl phosphate.
  • Ester quats are technical mixtures of optionally ethoxylated mono- and difatty acid triethanolamine esters which are quaternized with ethylene oxide, alkyl halides, dialkyl sulfates or dialkyl phosphates. They are also known substances. Esterquats are preferably used which are derived from tallow, coconut and / or palm fatty acids with an iodine number in the range 0 to 40 and have a degree of esterification of 1.5 to 1.9. The degree of ethoxylation can be 0 or 1 to 5, preferably 1 to 3.
  • Esterquats of the formula (IV) in which RO represents a methyl group or a polyethylene glycol chain having 1 to 3 ethylene oxide units and Y represents chloride or methyl sulfate are particularly suitable for reasons of application technology.
  • a methylquaternized dimethyl fatty acid triethanolamine ester (Dehyquart ( R ) AU36, Pulcra / Barcelona) is particularly preferred.
  • the polyhydroxy fatty acid amides and the monomeric cationic surfactants can be present in the detergent mixtures in a weight ratio of 1:10 to 10 s 1, preferably 1: 1 to 7: 1, based on the mixtures.
  • the detergent mixtures according to the invention can be prepared by simple stirring, if appropriate at a slightly elevated temperature (30 to 40 ° C.). This is a purely mechanical process, there is no chemical reaction. Anhydrous or highly concentrated starting materials can be used for the production, which are then diluted with water to the desired application concentration. However, it is also possible to mix dilute solutions.
  • Another object of the invention relates to a method for setting hair, in which one contains hair in a manner known per se with detergent mixtures a) polyhydroxy fatty acid amides of the formula (I)
  • R 1 CO for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R 2 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 10 carbon atoms and 3 to 10 hydroxyl groups
  • the detergent mixture depending on the fullness of the hair and the length of the hair, is applied in an amount of, for example, 15 to 25 ml to the washed and terry hair and is evenly distributed. It is advisable to comb through the hair to ensure an even distribution of the hair fixative.
  • the hair is then rolled up on water wave curlers and air dried, preferably under a drying hood. However, it is also possible to do without rolling up and shaping the hair with a blow dryer brush and drying it at the same time (“blow drying").
  • Another object of the invention relates to hair fixatives containing
  • R * CO for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R 2 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 10 carbon atoms and 3 to 10 hydroxyl groups
  • the hair fixatives are preferably in the form of liquid aqueous and / or alcoholic, in particular ethanolic, solutions with an active substance content of about 5 to 30, preferably 10 to 20,% by weight, based on the solution.
  • they can, for example, film-forming polymers, such as polyvinyl pyrrolidone and / or polyvinyl acetate, dyes, perfumes, UV adsorbers, thickeners.
  • film-forming polymers such as polyvinyl pyrrolidone and / or polyvinyl acetate
  • dyes such as polyvinyl pyrrolidone and / or polyvinyl acetate
  • dyes such as polyvinyl pyrrolidone and / or polyvinyl acetate
  • dyes such as polyvinyl pyrrolidone and / or polyvinyl acetate
  • dyes such as polyvinyl pyrrolidone and / or polyvinyl acetate
  • dyes such as
  • Detergent mixtures containing polyhydroxy fatty acid amides, protein hydrolyzates and optionally monomeric cationic surfactants show film-forming and conditioning properties. They give the hair hold, fullness, manageability, firmness and bounce.
  • Another object of the invention therefore relates to the use of detergent mixtures containing
  • hair fixatives for the production of hair fixatives, in which they can be present in amounts of 10 to 95, preferably 30 to 80% by weight, based on the composition.
  • the examples and comparative examples show that formulations which contain polyhydroxyfatty acid amides and protein hydrolyzates as nonionic surfactants, in comparison to mere water treatment (water wave) and formulations which contain polyhydroxyfatty acid amides as nonionic surfactants alone, improve the jumping power, expressed by higher stretching work , Oscillation frequencies and initial amplitudes. Together with the increased vibration, an increased friction in the hair bandage and thus also an increased damping is observed. It makes no difference whether combed curls or combed curls are considered. With the former, the effect is particularly clear, since the strongly bonded strand bandage must be made to vibrate.
  • Table 4 shows the vibration behavior of curls.
  • the measured values represent the damping of the maxima, the O-amplitude of the maxima and the stretching work of the combed-out curls at 15% relative air humidity.

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

Abstract

Des mélanges de détergents contenant des amides d'acide gras de polyhydroxy de formule (I), dans laquelle R1CO représente un groupe acyle aliphatique avec 6 à 22 atomes de carbone, R2 est hydrogène, un groupe alkyle ou un groupe hydroxyalkyle avec 1 à 4 atomes de carbone et [Z] est un groupe polyhydroxyalkyle linéaire ou ramifié avec 3 à 10 atomes de carbone et 3 à 10 groupes hydroxyle, des hydrolysats protéiques avec un poids moléculaire moyen dans la plage de 1000 à 6000 et des tensioactifs cationiques monomères, renforcent la souplesse des cheveux et peuvent s'utiliser dans des fixateurs capillaires.
PCT/EP1994/000807 1993-03-24 1994-03-15 Melanges de detergents WO1994021771A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP6520634A JPH08508055A (ja) 1993-03-24 1994-03-15 洗剤混合物
EP94911890A EP0690907A1 (fr) 1993-03-24 1994-03-15 Melanges de detergents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4309567A DE4309567A1 (de) 1993-03-24 1993-03-24 Detergensgemische
DEP4309567.4 1993-03-24

Publications (1)

Publication Number Publication Date
WO1994021771A1 true WO1994021771A1 (fr) 1994-09-29

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ID=6483729

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/000807 WO1994021771A1 (fr) 1993-03-24 1994-03-15 Melanges de detergents

Country Status (4)

Country Link
EP (1) EP0690907A1 (fr)
JP (1) JPH08508055A (fr)
DE (1) DE4309567A1 (fr)
WO (1) WO1994021771A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8293220B2 (en) 2009-05-28 2012-10-23 Shiseido Company, Ltd. Hair cosmetic
US11116220B2 (en) 2017-12-22 2021-09-14 Ecolab Usa Inc. Antimicrobial compositions with enhanced efficacy
CN113423470A (zh) * 2019-02-13 2021-09-21 三吉油脂株式会社 化妆品配合剂、化妆品及其制造方法

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19524097A1 (de) * 1995-07-01 1997-01-02 Henkel Kgaa Kosmetische Mittel
DE19533539A1 (de) * 1995-09-11 1997-03-13 Henkel Kgaa O/W-Emulgatoren
DE19544710C2 (de) 1995-11-30 1998-11-26 Henkel Kgaa Verdickungsmittel
DE19548068C1 (de) 1995-12-21 1997-06-19 Henkel Kgaa Verfahren zur Herstellung hellfarbiger, niedrigviskoser Tensidkonzentrate
DE19547986C1 (de) * 1995-12-21 1997-07-10 Henkel Kgaa O/W-Mikroemulsionen
US5932535A (en) * 1995-12-21 1999-08-03 Henkel Kommanditgesellschaft Auf Aktien Process for the production of light-colored, low-viscosity surfactant concentrates
US6033652A (en) * 1996-05-15 2000-03-07 Henkel Kommanditgesellschaft Auf Aktien Hair-treatment formulations
DE10018812A1 (de) 2000-04-15 2001-10-25 Cognis Deutschland Gmbh Verfahren zur Herstellung von nichtionischen Tensidgranulaten
DE10132173A1 (de) 2001-07-03 2003-01-23 Goldschmidt Ag Th Neue Betainester
DE102005025933B3 (de) 2005-06-06 2006-07-13 Centrotherm Photovoltaics Gmbh + Co. Kg Dotiergermisch für die Dotierung von Halbleitern
JP4657354B2 (ja) * 2009-05-28 2011-03-23 株式会社資生堂 毛髪化粧料
DE102013225843A1 (de) * 2013-12-13 2015-06-18 Henkel Ag & Co. Kgaa Kosmetische Zusammensetzung enthaltend eine Kombination aus Carbonsäure-N-alkylpolyhydroxyalkylamiden und Ceramiden
CN113423800A (zh) * 2019-02-13 2021-09-21 三吉油脂株式会社 包含有机铵盐的组合物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2116568A (en) * 1982-03-15 1983-09-28 Colgate Palmolive Co Agent for reducing detergent irritation to skin and eyes
WO1992006160A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Systemes tensioactifs non ioniques contenant des amides d'acides gras de polyhydroxy et un ou plusieurs tensioactifs non ioniques supplementaires

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2116568A (en) * 1982-03-15 1983-09-28 Colgate Palmolive Co Agent for reducing detergent irritation to skin and eyes
WO1992006160A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Systemes tensioactifs non ioniques contenant des amides d'acides gras de polyhydroxy et un ou plusieurs tensioactifs non ioniques supplementaires

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Derwent World Patents Index; *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8293220B2 (en) 2009-05-28 2012-10-23 Shiseido Company, Ltd. Hair cosmetic
US11116220B2 (en) 2017-12-22 2021-09-14 Ecolab Usa Inc. Antimicrobial compositions with enhanced efficacy
US11930819B2 (en) 2017-12-22 2024-03-19 Ecolab Usa Inc. Antimicrobial compositions with enhanced efficacy
CN113423470A (zh) * 2019-02-13 2021-09-21 三吉油脂株式会社 化妆品配合剂、化妆品及其制造方法

Also Published As

Publication number Publication date
EP0690907A1 (fr) 1996-01-10
DE4309567A1 (de) 1994-09-29
JPH08508055A (ja) 1996-08-27

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