EP0689420A1 - Melanges de detergents presentant des caracteristiques d'avivage ameliorees - Google Patents

Melanges de detergents presentant des caracteristiques d'avivage ameliorees

Info

Publication number
EP0689420A1
EP0689420A1 EP94911888A EP94911888A EP0689420A1 EP 0689420 A1 EP0689420 A1 EP 0689420A1 EP 94911888 A EP94911888 A EP 94911888A EP 94911888 A EP94911888 A EP 94911888A EP 0689420 A1 EP0689420 A1 EP 0689420A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
alkyl
detergent mixtures
contain
acid amides
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.)
Withdrawn
Application number
EP94911888A
Other languages
German (de)
English (en)
Inventor
Hermann Hensen
Holger Tesmann
Jörg KAHRE
Reinhard Müller
Wolfhard Scholz
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 EP0689420A1 publication Critical patent/EP0689420A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • C11D1/525—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

Definitions

  • the invention relates to detergent mixtures containing polyhydroxyfatty acid amides, monomeric cationic surfactants and, where appropriate, oil bodies, hair treatment compositions which contain these mixtures and the use of the mixtures for the production of hair treatment compositions.
  • Modern hair treatment and hair care products usually contain polymeric cationic surfactants, the task of which is to improve the combability of the strands of hair and to provide an antistatic finish.
  • the effectiveness of the cationic polymers is usually improved in a synergistic manner by the selection of further surfactant components.
  • JP-A 01/144 497 discloses hair shampoos which, in addition to cationic polymers and quaternary ammonium compounds, contain alkyl polyglucosides and anionic surfactants.
  • DE-A 30 18 600 L'Oreal
  • a hair shampoo is proposed in Example 16, which besides cationic starch also contains alkyl polyglucosides and saponins.
  • EP-AI 0 337 354 relates to mild surfactant mixtures containing alkyl polyglucosides and cationic polymers.
  • the object of the invention was therefore to provide new detergent mixtures based on monomeric cationic surfactants, which have an advantageous hair conditioner and also have a high dermatological and ecotoxicological compatibility.
  • the invention relates to detergent mixtures with improved softening properties, containing a) polyhydroxy fatty acid amides of the formula (I)
  • 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
  • [ZJ for a linear or branched polyhydroxyalkyl radical with 3 to 10 carbon atoms and 3 to 10 Hydroxyl groups
  • mixtures of polyhydroxy fatty acid amides, in particular fatty acid N-alkylglucamides, and monomeric cationic surfactants show excellent hair conditioner and this effect can be significantly increased by the use of oil bodies.
  • the mixtures are particularly kind to the skin and readily biodegradable.
  • the polyhydroxy fatty acid amides are known substances which are usually 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 can be obtained.
  • 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 can be obtained.
  • the detergent mixtures according to the invention preferably contain polyhydroxy fatty acid amides of the formula (I) in which R ⁇ O is an acyl radical having 12 to 22 carbon atoms, R 2 is hydrogen or a methyl group, and [Z] is a reduced glucose radical.
  • the preferred polyhydroxy fatty acid amides are therefore fatty acid N-alkylglucamides, as represented by the formula (II):
  • Preferably used as polyhydroxy fatty acid amides are fatty acid N-alkylglucamides of the formula (II) in which R 2 represents hydrogen or a methyl group and R ⁇ -CO represents the acyl radical of lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid , Elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachinic 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 radical of lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid , Elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachinic acid,
  • Fatty acid N-alkylglucamides of the formula (II) which are obtained by reductive amination of glucose with methylamine and subsequent ones are particularly preferred Acylation with lauric acid or Ci2 / 14 -K ° cos fatty acid or a corresponding derivative can be obtained.
  • Suitable monomeric cationic surfactants are quaternary ammonium compounds (QAC) of the formula (III)
  • R ⁇ for an optionally hydroxy-substituted alkyl and / or alkenyl radical with 6 to 22 carbon atoms
  • X represents halogen, alkyl sulfate or alkyl phosphate.
  • the QAC are known substances which can be obtained by the relevant preparative organic chemistry processes.
  • One method for their preparation consists, for example, in quaternizing tertiary amines with methyl chloride or dimethyl sulfate.
  • R ⁇ for an optionally hydroxyl-substituted alkyl radical with 16 to 18 carbon atoms
  • R 4 represents R ⁇ , a methyl or hydroxyethyl group
  • R5 and R> represents a methyl group
  • X represents chloride or methyl sulfate.
  • ester sulfates of the formula (IV) Another group in the sense of the invention of suitable monomeric cationic surfactants are the ester sulfates of the formula (IV)
  • 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. Ester quats are preferably used which are derived from palm, coconut or tallow fatty acids with an iodine number in the range from 0 to 40 and have a degree of esterification from 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 R8 stands for a methyl group or a polyethylene glycol chain with 1 to 3 ethylene oxide units and Y for chloride or methyl sulfate are particularly suitable for technical reasons.
  • a methyl-quaternized dipalm, dicocoate or ditallow fatty acid triethanolamine ester (Dehyquart ( R ) AU36, Pulcra / Barcelona) is particularly preferred.
  • Suitable oil bodies are, for example, fatty oils, fatty acid esters, Guerbet alcohols, dialkylcyclohexanes, dialkyl ethers, paraffinic hydrocarbons and silicone oils.
  • Fatty oils are to be understood as synthetic, but preferably natural triglycerides which contain a high proportion of unsaturated fatty acids and have an iodine number in the range from 100 to 170.
  • Typical examples are rapeseed and sunflower oil from new cultivation, peanut oil, cottonseed oil, coriander oil, olive oil, meadowfoam oil, avocado oil, almond oil and nut oil.
  • Suitable fatty acid esters are compounds of the formula (V),
  • Guerbet alcohols are compounds of the formula (VI)
  • Typical examples are 2-hexyldecanol, 2-0ctyldodecanol and 2-decyltetradecanol.
  • dialkylcyclohexanes are known substances that can be obtained by relevant processes in preparative organic chemistry.
  • An example of their preparation consists, for example, in subjecting dialkyl aromatics (ortho / meta / para-xylene) from the BTX fraction of the petroleum to a catalytic hydrogenation.
  • R 11 and R 2 independently of one another are alkyl radicals having 1 to 12 carbon atoms and [C] is a cyclohexyl radical.
  • Typical examples are dimethylcyclohexane, diethylcyclohexane, methylethylcyclohexane, dipropylcyclohexane, di-n-butylcyclohexane, di-tert.butylcyclohexane, di-2-ethylhexylcyclohexane and in particular di-n-octylcylohexane.
  • Dialkylethers are compounds of the formula (VTII)
  • R 13_o-R 14 (VTII) in which R 13 and R 14 independently of one another represent alkyl radicals having 6 to 22 carbon atoms.
  • the preferred di-alkyl ethers in the sense of the invention are thus di-n-octyl ether and di-2-ethylhexyl ether.
  • Paraffin hydrocarbons are to be understood as known technical alkane mixtures, as are usually used as oil bodies in cosmetic products. These are preferably thin liquid paraffins which have a density of 0.81 to 0.875.
  • silicon oil encompasses the group of polyorganosiloxanes in which silicon atoms are linked in a chain and / or network manner via oxygen atoms and the remaining valences are saturated by alkyl groups.
  • Typical examples of silicone oils which can be used as suitable oil bodies are cosmetics in perfume. .62, 232 (1986).
  • the polyhydroxy fatty acid amides and the monomeric cationic surfactants can usually be used in a weight ratio of 1: 3 to 3: 1, preferably 1: 2 to 2: 1. The same ratios are also recommended for the use of polyhydroxy fatty acid amides and oil bodies.
  • Another object of the invention relates to aqueous hair treatment compositions containing
  • hair treatment agents are in particular hair rinses and hair shampoos as well as "two-in-one" combinations of both products, which give the hair combability and shine and are also intended to reduce the anti-static charge.
  • the cationic surfactants and, if appropriate, the oil bodies can also be used in minor amounts of other surfactants.
  • Typical examples are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, ether carboxylic acids, alkyl amido betaines or protein fatty acid condensates.
  • emulsifiers such as alkoxylated fatty alcohols or sorbitan esters are also suitable.
  • Substances such as polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone and also polyvinyl alcohol and ammonium chloride.
  • Biogenic active substances are, for example, plant extracts, protein hydrolyzates and vitamin complexes.
  • Common film formers are, for example, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentadiol or sorbic acid.
  • Suitable pearlizing agents are, for example, glycol dietearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters.
  • Substances suitable and approved for cosmetic purposes can be used as dyes, as described, for example, in the publication "Cosmetic Dyes" of the Dye Commission of the German Research Foundation. shaft, published by Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can make up 0 to 50, preferably 5 to 40,% by weight, based on the solids content of the overall mixture.
  • the detergent mixtures according to the invention improve the wet and dry combability of hair, reduce the electrostatic charge, give hair a pleasant soft feel and a silky shine.
  • the invention thus offers for the first time a teaching according to which hair treatment agents with satisfactory properties can be produced on the basis of monomeric cationic surfactants and polyhydroxy fatty acid amides.
  • Another object of the invention therefore relates to the use of the detergent mixtures according to the invention for the production of aqueous hair treatment compositions in which they are present in amounts of 1 to 100, preferably 5 to 70% by weight, based on the solids content of the compositions can.
  • Emulsifier cetylstearyl alcohol
  • Formulations A to K are according to the invention, formulations U and V are used for comparison.
  • the dry combability was examined with approval of the electrostatic charge.
  • a relative air humidity of 20% was set.
  • the conditioning time was 12 h at 30 ° C.
  • the measurement was carried out by tapping the load on a double Faraday cage after performing 10 combs.
  • the error in the measurements was 2.5% on average, the statistical safety was at least 99.9%.
  • the results of the combing work are shown in Table 2.

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

Abstract

Des mélanges de détergents renfermant a) 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 bien 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, b) des tensioactifs cationiques monomères et, le cas échéant, c) des substances huileuses, facilitent le coiffage des cheveux secs et mouillés et conviennent pour produire des agents de traitement capillaire aqueux.
EP94911888A 1993-03-24 1994-03-15 Melanges de detergents presentant des caracteristiques d'avivage ameliorees Withdrawn EP0689420A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4309568 1993-03-24
DE4309568A DE4309568A1 (de) 1993-03-24 1993-03-24 Detergensgemische mit verbesserten Avivageeigenschaften
PCT/EP1994/000799 WO1994021226A1 (fr) 1993-03-24 1994-03-15 Melanges de detergents presentant des caracteristiques d'avivage ameliorees

Publications (1)

Publication Number Publication Date
EP0689420A1 true EP0689420A1 (fr) 1996-01-03

Family

ID=6483730

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94911888A Withdrawn EP0689420A1 (fr) 1993-03-24 1994-03-15 Melanges de detergents presentant des caracteristiques d'avivage ameliorees

Country Status (4)

Country Link
EP (1) EP0689420A1 (fr)
JP (1) JPH08508021A (fr)
DE (1) DE4309568A1 (fr)
WO (1) WO1994021226A1 (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19507531C2 (de) * 1995-03-03 1998-07-09 Henkel Kgaa Verwendung von Fettsäure-N-alkylpolyhydroxyalkylamiden
DE19623763C2 (de) * 1996-06-14 1999-08-26 Henkel Kgaa Kosmetische Zubereitungen
FR2751532B1 (fr) * 1996-07-23 1998-08-28 Oreal Compositions lavantes et conditionnantes a base de silicone et de dialkylether
DE19635195C1 (de) * 1996-08-30 1998-01-29 Henkel Kgaa Kosmetische Zubereitungen und Verfahren zu ihrer Herstellung
FR2767133B1 (fr) * 1997-08-08 1999-09-24 Ceca Sa Ammonium quaternaires d'alkylamino alditols,procede de preparation,compositions les contenant et utilisations, notamment dans le domaine de la cosmetique
DE19815461A1 (de) * 1998-04-07 1999-10-14 Wella Ag Flüssige kosmetische Zusammensetzung
EP1413285A1 (fr) * 2002-10-23 2004-04-28 Cognis Iberia, S.L. Compositions d'apres-shampooing contenant des tensioactifs cationiques, des huiles et des alcohols d'acides gras
JP4756249B2 (ja) * 2006-11-07 2011-08-24 山栄化学株式会社 多剤式毛髪化粧料
JP5284703B2 (ja) * 2008-07-17 2013-09-11 クラシエホームプロダクツ株式会社 ヘアリンス組成物
US20150150767A1 (en) 2012-05-30 2015-06-04 Clariant Finance (Bvi) Limited Compositions Containing Fatty Alcohols, Cationic Surfactants And N-Acyl-N-Methylglucamines
JP5936066B2 (ja) * 2012-12-13 2016-06-15 株式会社スリーボンド 洗浄剤組成物
DE102013018000A1 (de) 2013-11-29 2015-06-03 Clariant International Ltd. Konditioniershampoos enthaltend anionische Tenside, Glucamide und Fettalkohole
DE102013018001A1 (de) 2013-11-29 2015-06-03 Clariant International Ltd. Verwendung von Glucamiden zur Verbesserung der Silikondeposition
DE202013011413U1 (de) 2013-12-20 2014-01-27 Clariant International Ltd. Konditioniershampoos enthaltend anionische Tenside, Glucamide und Fettalkohole
DE202013011412U1 (de) 2013-12-20 2014-01-27 Clariant International Ltd. Glucamide zur Verbesserung der Silikondeposition
WO2019126703A1 (fr) 2017-12-22 2019-06-27 Ecolab Usa Inc. Compositions antimicrobiennes à efficacité améliorée
EP3533435B1 (fr) * 2018-02-28 2022-07-13 Kao Corporation Composition de nettoyage et de conditionnement pour fibres de kératine, procédé, utilisation et kit de pièces associé
US20220096349A1 (en) * 2019-02-13 2022-03-31 Miyoshi Oil & Fat Co., Ltd. Cosmetic compounding agent, cosmetic and production method thereof
JP7490580B2 (ja) * 2019-02-13 2024-05-27 ミヨシ油脂株式会社 有機アンモニウム塩を含む組成物

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JPH06501699A (ja) * 1990-09-28 1994-02-24 ザ、プロクター、エンド、ギャンブル、カンパニー 改良シャンプー組成物
SK25193A3 (en) * 1990-09-28 1993-07-07 Procter & Gamble Detergent composition containing polyhydroxy fatty acid amides and alkyl ester sulfonate surfactants
ATE157392T1 (de) * 1990-09-28 1997-09-15 Procter & Gamble Polyhydroxyfettsäureamide und ein oder mehrere zusätzliche nichtionische tenside enthaltende nichtionische tensidsysteme

Non-Patent Citations (1)

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Also Published As

Publication number Publication date
DE4309568A1 (de) 1994-09-29
WO1994021226A1 (fr) 1994-09-29
JPH08508021A (ja) 1996-08-27

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