WO1997047284A1 - Cosmetic preparations based on cationic and non ionic surfactants - Google Patents

Cosmetic preparations based on cationic and non ionic surfactants Download PDF

Info

Publication number
WO1997047284A1
WO1997047284A1 PCT/EP1997/002898 EP9702898W WO9747284A1 WO 1997047284 A1 WO1997047284 A1 WO 1997047284A1 EP 9702898 W EP9702898 W EP 9702898W WO 9747284 A1 WO9747284 A1 WO 9747284A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
alkyl
radical
contain
formula
Prior art date
Application number
PCT/EP1997/002898
Other languages
German (de)
French (fr)
Inventor
Jörg KAHRE
Ester Prat Queralt
Norbert Boyxen
Bernhard Guckenbiehl
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 EP97928146A priority Critical patent/EP0910338A1/en
Priority to JP10501151A priority patent/JP2000512286A/en
Publication of WO1997047284A1 publication Critical patent/WO1997047284A1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/596Mixtures of surface active compounds

Definitions

  • the invention relates to cosmetic preparations with improved sensory properties for use in skin and hair care, containing esterquats and selected surfactants in binary or ternary mixtures.
  • Esterquats are cationic surfactants which, because of their excellent ecotoxicological properties, are becoming increasingly important both for the area of fabric softeners and for cosmetic applications. Overviews on this topic have been published, for example, by R.Puchta et al. in tens. Surf. Det., 30, 186 (1993), M.Brock in Tens. Surf. Det. 30, 394 (1993), R. Lagerman et al. in J. Am. Oil. Chem. Soc, 71, 97 (1994) and I. Shapiro et al. in Cosm.Toil. 109, 77 (1994) appeared.
  • esterquats In cosmetic preparations, esterquats, preferably together with fatty alcohols, are used to achieve a pleasant, soft skin and hair feeling. They can be contained in emulsions and lotions for skin care as well as in surfactants such as shampoos, shower baths, rinses, conditioners and the like for hair care.
  • the disadvantage here is that the desired soft feel of the skin and hair is perceived as dull and dry, while the consumer desires a soft, smooth feel.
  • the object of the present invention is therefore to add ester quats in such a way that low-viscosity, storage-stable concentrates result which have the desired sensor properties and are self-emulsifying in water.
  • the invention relates to cosmetic preparations containing
  • esters is generally understood to mean quaternized fatty acid triethanol amine ester salts. These are known substances which can be obtained by the relevant methods of preparative organic chemistry. In this connection, reference is made to the international patent application WO 91 / 01295 (Henkel), according to which triethanolamine is partially esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and then quaternized with dimethyl sulfate or ethylene oxide. The quaternized fatty acid triethanolamine ester salts follow the formula (I)
  • R'CO for an acyl radical with 6 to 22 carbon atoms
  • R 2 and R 3 independently of one another for hydrogen or R 1 CO
  • R 4 for an alkyl radical with 1 to 4 carbon atoms or a (CH 2 CH 2 0) q H- Group
  • q for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate.
  • ester quats that can be used in the sense of the invention are products based on caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid and theirs Technical blends, such as those that occur when natural fats and oils are split.
  • Technical Ci2 / i8 coconut fatty acids and in particular partially hardened Ci ⁇ / i ⁇ tallow or palm fatty acids as well as elaidic acid-rich Ci6 / 18 fatty acid cuts are preferably used.
  • the fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1 to produce the quaternized esters.
  • an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous.
  • the preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical C16 / "tallow or palm fatty acid (iodine number 0 to 40).
  • quaternized fatty acid triethanolamine ester salts of the formula (I) have proven to be particularly advantageous in which R 1 CO for an acyl radical having 16 to 18 carbon atoms, R 2 for R 1 CO, R 3 for hydrogen, R 4 for a methyl group, m , n and p is 0 and X is methyl sulfate.
  • quaternized ester salts of fatty acids with diethanolalkylamines of the formula (II) are also suitable as ester quats.
  • R 1 CO for an acyl radical with 6 to 22 carbon atoms
  • R 2 for hydrogen or R 1 CO
  • R 4 and R 5 independently of one another for alkyl radicals with 1 to 4 carbon atoms
  • m and n in total for 0 or numbers from 1 to 12
  • X represents halide, alkyl sulfate or alkyl phosphate.
  • ester quats are the quaternized ester salts of fatty acids with 1,2-dihydroxypropyl dialkylamines of the formula (III)
  • R 1 CO for an acyl radical having 6 to 22 carbon atoms
  • R 2 for hydrogen or R 1 CO
  • R 4 , R 5 and R 7 independently of one another for alkyl radicals with 1 to 4 carbon atoms
  • m and n in total for 0 or Numbers from 1 to 12
  • X represents halide, alkyl sulfate or alkyl phosphate.
  • esterquats of the formulas (II) and (III).
  • the esterquats usually come on the market in the form of 50 to 90% strength by weight alcoholic solutions, which can be diluted with water if required.
  • Sorbitan esters which form component (b1) are known nonionic surfactants which are usually obtained by esterifying sorbitan with fatty acids.
  • Typical sorbitan esters follow the formula (IV) in which
  • R 8 CO represents an aliphatic, saturated or unsaturated acyl radical having 6 to 22 and preferably 12 to 18 carbon atoms.
  • Formula (IV) represents a sorbitan monoester; however, the esters can also be present as sesquiesters, diesters, triesters or their technical mixtures. Typical Examples are the corresponding esters of sorbitan with lauric acid, palmitic acid, stearic acid, isostearic acid or oleic acid.
  • polyol poly-12-hydroxystearates which form component (b2) are known substances which are sold, for example, under the Dehymuls® PGPH brand [cf. DE-A1 44 20
  • the polyol component of the emulsifiers can be derived from substances which have at least two, preferably 3 to 12 and in particular 3 to 8 hydroxyl groups and 2 to 12 carbon atoms. Typical examples are:
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Alkyl oligoglucosides with 1 to 22, preferably 1 to 8 and in particular 1 to 4 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Aminosugars such as glucamine.
  • reaction products based on polyglycerol are of particular importance because of their excellent performance properties.
  • the use of selected polyglycerols which have the following homolog distribution has proven to be particularly advantageous (the preferred ranges are given in brackets):
  • esters of glycerol with one, two or three fatty acids with 6 to 22 and preferably 12 to 18 carbon atoms are examples.
  • Typical examples are vegetable oils, such as almond oil, or technical partial glycerides such as, for example, monoglycerides based on lauric acid, palmitic acid, stearic acid, isostearic acid and / or oleic acid.
  • Technical partial glycerides of fatty acids with 12 to 18 carbon atoms are preferably used.
  • Alkyl and alkenyl oligoglycosides which form component (d) are known nonionic surfactants which follow the formula (V)
  • R 9 represents an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G represents a sugar radical having 5 or 6 carbon atoms
  • p represents numbers from 1 to 10.
  • 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 oligoglucosides.
  • the index number p in the general formula (V) indicates the degree of oligomerization (DP), i.e. H. the distribution of mono- and oligoglycosides is present and stands for a number between 1 and 10.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R 9 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 from Roelen's oxosynthesis, for example in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes.
  • the alkyl or alkenyl radical R 9 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, palm oleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and the technical mixtures described above, which can be obtained as well as their technical mixtures.
  • Alkyl oligoglucosides based on hydrogenated Ci ⁇ yu coconut alcohol with a DP of 1 to 3 are preferred.
  • Fatty acid N-alkylpolyhydroxyalkylamides which are suitable as component (c2) are nonionic surfactants which follow the formula (VI)
  • R 10 CO for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R 11 for hydrogen, an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms
  • [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. With regard to the processes for their production, reference is made to US Pat. Nos.
  • the fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkyl polyhydroxyalkylamides are therefore fatty acid N-alkylglucamides, as represented by the formula (VII):
  • the fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (VII) in which R 11 is hydrogen or an alkyl group and R 10 CO is the acyl radical of capric 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, behenic acid or erucic acid or their technical mixtures.
  • R 11 is hydrogen or an alkyl group
  • R 10 CO is the acyl radical of capric acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, Palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic
  • Fatty acid N-alkylglucamides of the formula (VII) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or Ci ⁇ m coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • the preparations according to the invention can contain components (a) and (b) in a weight ratio of 10:90 to 90:10, preferably 25:75 to 75:25 and in particular 40:60 to 60:40. If ternary mixtures are used, the weight ratio between components (b) and (c) can also again be 10:90 to 90:10, preferably 25:75 to 75:25 and in particular 40:60 to 60:40.
  • the cosmetic preparations contain the esterquats in admixture with fatty alcohols of the formula (VIII),
  • the esterquats and the fatty alcohols are preferably in a weight ratio of 10:90 to 90; 10 and in particular 25: 75 to 75: 25 used.
  • the two components can be mixed subsequently, but they are preferably prepared by quaternizing the fatty acid alkanolamine esters on which the esterquats are based in fatty alcohols as an inert solvent with dimethyl sulfate, as described, for example, in German Patent DE-C1 43 08 794 (Henkel). Corresponding mixtures are commercially available, for example, under the Dehyquart® F brand.
  • the preparations according to the invention can be used for the production of skin and hair treatment compositions. In the simplest case, it is sufficient to dilute the mixtures with water to an application concentration.
  • the agents such as, for example, creams, lotions, hair shampoos, hair lotions, bubble baths and the like, can furthermore, as further auxiliaries and additives, oil bodies, emulsifiers, superfatting agents, fats, waxes, stabilizers, consistency agents, thickeners, cation polymers, biogenic active substances , Film formers, preservatives, dyes and fragrances.
  • a typical preparation according to the invention has the following composition:
  • component (a) 10 to 30, preferably 20 to 25% by weight of component (a), 1 to 40, preferably 10 to 20% by weight of component (b), 1 to 40, preferably 15 to 35% by weight of component (c) and 0 to 80, preferably 20 to 75% by weight fatty alcohols
  • Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C 2 o-fatty acids with linear C6-C 2 o-fatty alcohols, esters of branched C6-Ci3- Carboxylic acids with linear C6-C2o fatty alcohols, esters of linear C ⁇ -Ci ⁇ fatty acids with branched alcohols, especially 2-ethylhexanol, esters of linear and / or branched fatty acids with polyhydric alcohols (such as dimer diol or trimer triol) and / or Guerbet alcohols , Triglycerides based on C6-C ⁇ o fatty acids, vegetable oils, branched primary alcohols, substituted cyclohexanes, Guerbet carbonates, dialkyl ethers and / or aliphatic or naphthenic hydrocarbons.
  • Nonionic, ampholytic and / or zwitterionic surface-active compounds which are distinguished by a lipophilic, preferably linear alkyl or alkenyl group and at least one hydrophilic group can be used as emulsifiers or co-emulsifiers.
  • This hydrophilic group can be both an ionogenic and a nonionic group.
  • Non-ionic emulsifiers contain as a hydrophilic group z.
  • Preferred agents are those which contain nonionic surfactants from at least one of the following groups as O / W emulsifiers:
  • Glycerin (a3) Glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated
  • Fatty acids with 6 to 22 carbon atoms and their ethylene oxide addition products (a4) alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs; (a5) adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil; (a6) polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricinoleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable.
  • adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are homogeneous mixtures, whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are those surface-active compounds that contain at least one in the molecule carry quaternary ammonium group and at least one carboxylate and one sulfonate group.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / i6-acylsarcosine.
  • W / O emulsifiers are:
  • Substances such as polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Typical examples of fats are glycerides; beeswax, paraffin wax or microwaxes may be used as waxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol.
  • Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used.
  • Fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms are primarily considered as consistency agents.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, furthermore higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as table salt and ammonium chloride.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as e.g. Luviquat® (BASF AG, Ludwigshafen / FRG), condensation products of polyglycols and amines, quaternized collagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat ⁇ L, Grünau GmbH), quaternized wheat polypeptides,
  • cationic silicone polymers such as e.g. Amidomethicone or Dow Corning, Dow Coring Co./US, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetrimamine (Carretine®, Sandoz / CH), polyaminopolyamides such as e.g. described in FR-A 22 52 840 and its crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, cationic guar gum such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese / US, quaternized ammonium salt polymers such as Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol / US.
  • cationic silicone polymers such as e.g. Amidomethicone or Dow Corning, Dow Coring Co./US, copolymers of adipic acid and
  • Biogenic active substances are understood to mean, for example, plant extracts and vitamin complexes.
  • octopirox can be used as an antidandruff agent.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
  • Suitable pearlizing agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters.
  • the dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, 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 total mixture.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

The proposal is for novel cosmetic preparations for use in the field of hair and skin care, containing (a) esterquats and (b1) sorbitane esters, (b2) polyol poly-12-hydroxy stearates and/or (b3) glycerides and possibly (c1) alkyl and/or alkenyl oligoglycosides and/or (c2) fatty acid-N-alkyl polyhydroxyalkyl amides. The agents are distinguished by improved softness in the hair and a particularly pleasant feel to the skin.

Description

KOSMETISCHE ZUBEREITUNGEN AUF BASIS VON KATIONISCHEN UND NICHTIONISCHEN TENSIDENCosmetic preparations based on cationic and nonionic surfactants
Gebiet der ErfindungField of the Invention
Die Erfindung betrifft kosmetische Zubereitungen mit verbesserten sensorischen Eigenschaften für die Anwendung in der Haut- und Haarpflege, enthaltend Esterquats und ausgewählte Tenside in binären bzw. ternären Mischungen.The invention relates to cosmetic preparations with improved sensory properties for use in skin and hair care, containing esterquats and selected surfactants in binary or ternary mixtures.
Stand der TechnikState of the art
Esterquats stellen kationische Tenside dar, die wegen ihrer ausgezeichneten ökotoxikologischen Eigenschaften sowohl für den Bereich der Wäscheweichspülmittel als auch für kosmetische Anwen¬ dungen zunehmend an Bedeutung gewinnen. Übersichten zu diesem Thema sind beispielsweise von R.Puchta et al. in Tens. Surf. Det., 30, 186 (1993), M.Brock in Tens. Surf. Det. 30, 394 (1993), R. Lagerman et al. in J. Am. Oil. Chem. Soc, 71, 97 (1994) sowie I.Shapiro et al. in Cosm.Toil. 109, 77 (1994) erschienen.Esterquats are cationic surfactants which, because of their excellent ecotoxicological properties, are becoming increasingly important both for the area of fabric softeners and for cosmetic applications. Overviews on this topic have been published, for example, by R.Puchta et al. in tens. Surf. Det., 30, 186 (1993), M.Brock in Tens. Surf. Det. 30, 394 (1993), R. Lagerman et al. in J. Am. Oil. Chem. Soc, 71, 97 (1994) and I. Shapiro et al. in Cosm.Toil. 109, 77 (1994) appeared.
In kosmetischen Zubereitungen werden Esterquats, vorzugsweise zusammen mit Fettalkoholen, zur Erzielung eines angenehmen weichen Haut- und Haargefühls eingesetzt. Sie können dabei sowohl in Emulsionen und Lotionen zur Hautpflege wie auch in tensidischen Mitteln wie beispielsweise Sham- poos, Duschbädern, Spülungen, Conditionern und dergleichen für die Haarpflege enthalten sein. Nachteilig ist hierbei jedoch, daß der erwünschte weiche Griff der Haut und des Haares als stumpf und trocken empfunden wird, während vom Verbraucher ein weicher, glatter Griff gewünscht wird. Der vorliegenden Erfindung hat daher die Aufgabe zugrundegelegen, Esterquats in solcher Weise zu additivieren, daß niedrig viskose, lagerstabile Konzentrate resultieren, die die gewünschten sensori¬ schen Eigenschaften aufweisen und in Wasser selbstemulgierend sind.In cosmetic preparations, esterquats, preferably together with fatty alcohols, are used to achieve a pleasant, soft skin and hair feeling. They can be contained in emulsions and lotions for skin care as well as in surfactants such as shampoos, shower baths, rinses, conditioners and the like for hair care. The disadvantage here, however, is that the desired soft feel of the skin and hair is perceived as dull and dry, while the consumer desires a soft, smooth feel. The object of the present invention is therefore to add ester quats in such a way that low-viscosity, storage-stable concentrates result which have the desired sensor properties and are self-emulsifying in water.
Beschreibung der ErfindungDescription of the invention
Gegenstand der Erfindung sind kosmetische Zubereitungen, enthaltendThe invention relates to cosmetic preparations containing
(a) Esterquats und(a) Esterquats and
(b1) Sorbitanester,(b1) sorbitan esters,
(b2) Polyolpoly-12-hydroxystearate und/oder(b2) polyol poly-12-hydroxystearate and / or
(b3) Glyceride sowie gegebenenfalls(b3) glycerides and optionally
(d ) Alkyl- und/oder Alkenyloligoglykoside und/oder(d) alkyl and / or alkenyl oligoglycosides and / or
(c2) Fettsäure-N-alkylpolyhydroxyalkylamide.(c2) Fatty acid N-alkyl polyhydroxyalkyl amides.
Überraschenderweise wurde gefunden, daß der Zusatz von Stoffen, die die Komponente (b) bilden, den Weichgriff von Esterquats sowie deren hautsensorischen Eigenschaften signifikant verbessern. Eine weitere Steigerung der Eigenschaften kann erzielt werden, wenn man den Gemischen von Ester¬ quats mit den Stoffen der Gruppe (b) die weitere Komponente (c) zusetzt. Die resultierenden Konzen¬ trate sind wasserfrei, niedrigviskos, lagerstabil und beim Eintragen in wäßrige Phasen selbstemul¬ gierend.Surprisingly, it was found that the addition of substances which form component (b) significantly improve the softness of esterquats and their skin-sensory properties. A further increase in the properties can be achieved if the further component (c) is added to the mixtures of ester quats with the substances of group (b). The resulting concentrates are anhydrous, low-viscosity, stable in storage and self-emulsifying when introduced into aqueous phases.
EsterquatsEsterquats
Unter der Bezeichnung „Esterquats" werden im allgemeinen quaternierte Fettsäuretriethanol-aminester- salze verstanden. Es handelt sich dabei um bekannte Stoffe, die man nach den einschlägigen Metho¬ den der präparativen organischen Chemie erhalten kann. In diesem Zusammenhang sei auf die Internationale Patentanmeldung WO 91/01295 (Henkel) verwiesen, nach der man Triethanolamin in Gegenwart von unterphosphoriger Säure mit Fettsäuren partiell verestert, Luft durchleitet und an¬ schließend mit Dimethylsulfat oder Ethylenoxid quaterniert. Die quaternierten Fettsäuretriethanolaminestersalze folgen der Formel (I),The term “esterquats” is generally understood to mean quaternized fatty acid triethanol amine ester salts. These are known substances which can be obtained by the relevant methods of preparative organic chemistry. In this connection, reference is made to the international patent application WO 91 / 01295 (Henkel), according to which triethanolamine is partially esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and then quaternized with dimethyl sulfate or ethylene oxide. The quaternized fatty acid triethanolamine ester salts follow the formula (I)
R4 R 4
I [R1CO-(OCH2CH2)mOCH2CH2-N+-CH2CH20-(CH2CH2θ)nR2] X- (I)I [R 1 CO- (OCH 2 CH2) mOCH2CH2-N + -CH2CH 2 0- (CH2CH2θ) nR 2 ] X- (I)
II.
CH2CH20(CH2CH20)pR3 CH 2 CH 2 0 (CH 2 CH 2 0) p R 3
in der R'CO für einen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 und R3 unabhängig voneinander für Wasserstoff oder R1CO, R4 für einen Alkylrest mit 1 bis 4 Kohlenstoffatomen oder eine (CH2CH20)qH- Gruppe, m, n und p in Summe für 0 oder Zahlen von 1 bis 12, q für Zahlen von 1 bis 12 und X für Halo- genid, Alkylsulfat oder Alkylphosphat steht. Typische Beispiele für Esterquats, die im Sinne der Erfin¬ dung Verwendung finden können, sind Produkte auf Basis von Capronsäure, Caprylsäure, Caprin- säure, Laurinsäure, Myristinsäure, Palmitinsäure, Isostearinsäure, Stearinsäure, Ölsäure, Elaidinsäure, Arachinsäure, Behensäure und Erucasäure sowie deren technische Mischungen, wie sie beispielsweise bei der Druckspaltung natürlicher Fette und Öle anfallen. Vorzugsweise werden technische Ci2/i8-Kokosfettsäuren und insbesondere teilgehärtete Ciβ/iβ-Talg- bzw. Palmfettsäuren sowie elaidinsäurereiche Ci6/18-Fettsäureschnitte eingesetzt. Zur Herstellung der quaternierten Ester können die Fettsäuren und das Triethanolamin im molaren Verhältnis von 1 ,1 : 1 bis 3 : 1 eingesetzt werden. Im Hinblick auf die anwendungstechnischen Eigenschaften der Esterquats hat sich ein Ein¬ satzverhältnis von 1 ,2 : 1 bis 2,2 : 1 , vorzugsweise 1,5 : 1 bis 1 ,9 : 1 als besonders vorteilhaft erwiesen. Die bevorzugten Esterquats stellen technische Mischungen von Mono-, Di- und Triestern mit einem durchschnittlichen Veresterungsgrad von 1,5 bis 1 ,9 dar und leiten sich von technischer C16/«- Talg¬ bzw. Palmfettsäure (lodzahl 0 bis 40) ab. Aus anwendungstechnischer Sicht haben sich quaternierte Fettsäuretriethanolaminestersalze der Formel (I) als besonders vorteilhaft erwiesen, in der R1CO für einen Acylrest mit 16 bis 18 Kohlenstoffatomen, R2 für R1CO, R3 für Wasserstoff, R4 für eine Methylgruppe, m, n und p für 0 und X für Methylsulfat steht.in the R'CO for an acyl radical with 6 to 22 carbon atoms, R 2 and R 3 independently of one another for hydrogen or R 1 CO, R 4 for an alkyl radical with 1 to 4 carbon atoms or a (CH 2 CH 2 0) q H- Group, m, n and p in total for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate. Typical examples of ester quats that can be used in the sense of the invention are products based on caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid and theirs Technical blends, such as those that occur when natural fats and oils are split. Technical Ci2 / i8 coconut fatty acids and in particular partially hardened Ciβ / iβ tallow or palm fatty acids as well as elaidic acid-rich Ci6 / 18 fatty acid cuts are preferably used. The fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1 to produce the quaternized esters. With regard to the application properties of the ester quats, an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous. The preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical C16 / "tallow or palm fatty acid (iodine number 0 to 40). From an application point of view, quaternized fatty acid triethanolamine ester salts of the formula (I) have proven to be particularly advantageous in which R 1 CO for an acyl radical having 16 to 18 carbon atoms, R 2 for R 1 CO, R 3 for hydrogen, R 4 for a methyl group, m , n and p is 0 and X is methyl sulfate.
Neben den quaternierten Fettsäuretriethanolaminestersalzen kommen als Esterquats femer auch qua¬ ternierte Estersalze von Fettsäuren mit Diethanolalkylaminen der Formel (II) in Betracht,In addition to the quaternized fatty acid triethanolamine ester salts, quaternized ester salts of fatty acids with diethanolalkylamines of the formula (II) are also suitable as ester quats.
R4 R 4
II.
[R1CO-(OCH2CH2)mOCH2CH2-N+-CH2CH2θ-(CH2CH2θ)nR2] X- (II)[R 1 CO- (OCH2CH 2 ) mOCH 2 CH2-N + -CH2CH2θ- (CH 2 CH2θ) nR 2 ] X- (II)
I Rs in der R1CO für einen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 für Wasserstoff oder R1CO, R4 und R5 unabhängig voneinander für Alkylreste mit 1 bis 4 Kohlenstoffatomen, m und n in Summe für 0 oder Zahlen von 1 bis 12 und X für Halogenid, Alkylsulfat oder Alkylphosphat steht.I Rs in which R 1 CO for an acyl radical with 6 to 22 carbon atoms, R 2 for hydrogen or R 1 CO, R 4 and R 5 independently of one another for alkyl radicals with 1 to 4 carbon atoms, m and n in total for 0 or numbers from 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate.
Als weitere Gruppe geeigneter Esterquats sind schließlich die quaternierten Estersalze von Fettsäuren mit 1 ,2-Dihydroxypropyldialkylaminen der Formel (III) zu nennen,Finally, a further group of suitable ester quats are the quaternized ester salts of fatty acids with 1,2-dihydroxypropyl dialkylamines of the formula (III)
R6 0-(CH2CH20)mOCR1 l+ IR 6 0- (CH2CH 2 0) mOCR 1 l + I
[R4-N+-CH2CHCH20-(CH2CH20)nR2] X" (III)[R 4 -N + -CH 2 CHCH 2 0- (CH 2 CH 2 0) n R 2 ] X "(III)
II.
R7R7
in der R1CO für einen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 für Wasserstoff oder R1CO, R4, R5 und R7 unabhängig voneinander für Alkylreste mit 1 bis 4 Kohlenstoff atomen, m und n in Summe für 0 oder Zahlen von 1 bis 12 und X für Halogenid, Alkylsulfat oder Alkylphosphat steht.in which R 1 CO for an acyl radical having 6 to 22 carbon atoms, R 2 for hydrogen or R 1 CO, R 4 , R 5 and R 7 independently of one another for alkyl radicals with 1 to 4 carbon atoms, m and n in total for 0 or Numbers from 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate.
Hinsichtlich der Auswahl der bevorzugten Fettsäuren und des optimalen Veresterungsgrades gelten die für (I) genannten Beispiele auch für die Esterquats der Formeln (II) und (III). Üblicherweise gelangen die Esterquats in Form 50 bis 90 Gew.-%iger alkoholischer Lösungen in den Handel, die bei Bedarf problemlos mit Wasser verdünnt werden können.With regard to the selection of the preferred fatty acids and the optimal degree of esterification, the examples given for (I) also apply to the esterquats of the formulas (II) and (III). The esterquats usually come on the market in the form of 50 to 90% strength by weight alcoholic solutions, which can be diluted with water if required.
SorbitanesterSorbitan esters
Sorbitanester, die die Komponente (b1) bilden, stellen bekannte nichtionische Tenside dar, die üblicher¬ weise durch Veresterung von Sorbitan mit Fettsäuren erhalten werden. Typische Sorbitanester folgen der Formel (IV), in derSorbitan esters which form component (b1) are known nonionic surfactants which are usually obtained by esterifying sorbitan with fatty acids. Typical sorbitan esters follow the formula (IV) in which
R8CO für einen aliphatischen, gesättigten oder ungesättigten Acylrest mit 6 bis 22 und vorzugsweise 12 bis 18 Kohlenstoffatomen steht. Formel (IV) gibt einen Sorbitanmonoester wieder; die Ester können jedoch auch als Sesquiester, Diester, Triester oder deren technische Mischungen vorliegen. Typische Beispiele sind die entsprechenden Ester des Sorbitans mit Laurinsäure, Palmitinsäure, Stearinsäure, Isostearinsäure oder Ölsäure.R 8 CO represents an aliphatic, saturated or unsaturated acyl radical having 6 to 22 and preferably 12 to 18 carbon atoms. Formula (IV) represents a sorbitan monoester; however, the esters can also be present as sesquiesters, diesters, triesters or their technical mixtures. Typical Examples are the corresponding esters of sorbitan with lauric acid, palmitic acid, stearic acid, isostearic acid or oleic acid.
Polyolpoly-12-hydroxystearatePolyol poly-12-hydroxystearate
Bei den Polyolpoly-12-hydroxystearaten, die die Komponente (b2) bilden, handelt es sich um bekannte Stoffe, die beispielsweise unter der Marke Dehymuls® PGPH vertrieben werden [vgl. DE-A1 44 20The polyol poly-12-hydroxystearates which form component (b2) are known substances which are sold, for example, under the Dehymuls® PGPH brand [cf. DE-A1 44 20
516], Die Polyolkomponente der Emulgatoren kann sich von Stoffen ableiten, die über mindestens zwei, vorzugsweise 3 bis 12 und insbesondere 3 bis 8 Hydroxylgruppen und 2 bis 12 Kohlenstoffatome verfügen. Typische Beispiele sind:516], The polyol component of the emulsifiers can be derived from substances which have at least two, preferably 3 to 12 and in particular 3 to 8 hydroxyl groups and 2 to 12 carbon atoms. Typical examples are:
• Glycerin und Polyglycerin;• glycerin and polyglycerin;
• Alkylenglycole, wie beispielsweise Ethylenglycol, Diethylenglycol, Propylenglycol;Alkylene glycols, such as, for example, ethylene glycol, diethylene glycol, propylene glycol;
• Methyolverbindungen, wie insbesondere Trimethylolethan, Trimethylolpropan, Trimethylolbutan, Pentaerythrit und Dipentaerythrit;• Methyl compounds, such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
• Alkyloligoglucoside mit 1 bis 22, vorzugsweise 1 bis 8 und insbesondere 1 bis 4 Kohlenstoffen im Alkylrest, wie beispielsweise Methyl- und Butylglucosid;Alkyl oligoglucosides with 1 to 22, preferably 1 to 8 and in particular 1 to 4 carbons in the alkyl radical, such as methyl and butyl glucoside;
• Zuckeralkohole mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Sorbit oder Mannit,Sugar alcohols with 5 to 12 carbon atoms, such as sorbitol or mannitol,
• Zucker mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Glucose oder Saccharose;• Sugar with 5 to 12 carbon atoms, such as glucose or sucrose;
• Aminozucker wie beispielsweise Glucamin.Aminosugars such as glucamine.
Unter den erfindungsgemäß einzusetzenden Emulgatoren kommt Umsetzungsprodukten auf Basis von Polyglycerin wegen ihrer ausgezeichneten anwendungstechnischen Eigenschaften eine besondere Be¬ deutung zu. Als besonders vorteilhaft hat sich die Verwendung von ausgewählten Polyglycerinen erwiesen, die die folgende Homologenverteilung aufweisen (in Klammern angegeben sind die bevor¬ zugten Bereiche):Among the emulsifiers to be used according to the invention, reaction products based on polyglycerol are of particular importance because of their excellent performance properties. The use of selected polyglycerols which have the following homolog distribution has proven to be particularly advantageous (the preferred ranges are given in brackets):
Glycerin 5 bis 35 (15 bis 30) Gew.-%Glycerin 5 to 35 (15 to 30) wt%
Diglycerine 15 bis 40 (20 bis 32) Gew.-%Diglycerols 15 to 40 (20 to 32) wt%
Triglycerine 10 bis 35 (15 bis 25) Gew.-%Triglycerols 10 to 35 (15 to 25)% by weight
Tetraglycerine 5 bis 20 ( 8 bis 15) Gew.-%Tetraglycerols 5 to 20 (8 to 15) wt%
Pentaglycerine 2 bis 10 ( 3 bis 8) Gew.-%Pentaglycerols 2 to 10 (3 to 8) wt%
Oligoglycerine ad 100 Gew.-% GlvcerideOligoglycerols ad 100% by weight Glvceride
Als Komponente (b3) kommen Ester des Glycerins mit einer, zwei oder drei Fettsäuren mit 6 bis 22 und vorzugsweise 12 bis 18 Kohlenstoffatomen in Betracht. Typische Beispiele sind pflanzliche Öle, wie beispielsweise Mandelöl, oder technische Partialglyceride wie beispielsweise Monoglyceride auf Basis von Laurinsäure, Palmitinsäure, Stearinsäure, Isostearinsäure und/oder Ölsäure. Vorzugsweise werden technische Partialglyceride von Fettsäuren mit 12 bis 18 Kohlenstoffatomen eingesetzt.As component (b3) are esters of glycerol with one, two or three fatty acids with 6 to 22 and preferably 12 to 18 carbon atoms. Typical examples are vegetable oils, such as almond oil, or technical partial glycerides such as, for example, monoglycerides based on lauric acid, palmitic acid, stearic acid, isostearic acid and / or oleic acid. Technical partial glycerides of fatty acids with 12 to 18 carbon atoms are preferably used.
Alkyl- und/oder AlkenyloliqoqlvkosideAlkyl and / or alkenyl oligonucleotides
Alkyl- und Alkenyloligoglykoside, die die Komponente (d) bilden, stellen bekannte nichtionische Tenside dar, die der Formel (V) folgen,Alkyl and alkenyl oligoglycosides which form component (d) are known nonionic surfactants which follow the formula (V)
R90-[G]p (V)R 9 0- [G] p (V)
in der R9 für einen Alkyl- und/oder Alkenylrest mit 4 bis 22 Kohlenstoffatomen, G für einen Zuckerrest mit 5 oder 6 Kohlenstoffatomen und p für Zahlen von 1 bis 10 steht. Sie können nach den einschlä¬ gigen Verfahren der präparativen organischen Chemie erhalten werden. Stellvertretend für das umfang¬ reiche Schrifttum sei hier auf die Schriften EP-A1 0 301 298 und WO 90/03977 verwiesen.in which R 9 represents an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G represents a sugar radical having 5 or 6 carbon atoms and p represents numbers from 1 to 10. They can be obtained using the relevant preparative organic chemistry processes. As a representative of the extensive literature, reference is made here to the documents EP-A1 0 301 298 and WO 90/03977.
Die Alkyl- und/oder Alkenyloligoglykoside können sich von Aldosen bzw. Ketosen mit 5 oder 6 Kohlen¬ stoffatomen, vorzugsweise der Glucose ableiten. Die bevorzugten Alkyl- und/oder Alkenyloligoglykoside sind somit Alkyl- und/oder Alkenyloligoglucoside. Die Indexzahl p in der allgemeinen Formel (V) gibt den Oligomerisierungsgrad (DP), d. h. die Verteilung von Mono- und Oligoglykosiden an und steht für eine Zahl zwischen 1 und 10. Während p in einer gegebenen Verbindung stets ganzzahlig sein muß und hier vor allem die Werte p = 1 bis 6 annehmen kann, ist der Wert p für ein bestimmtes Alkyloligoglykosid eine analytisch ermittelte rechnerische Größe, die meistens eine gebrochene Zahl darstellt. Vorzugsweise werden Alkyl- und/oder Alkenyloligoglykoside mit einem mittleren Oligo¬ merisierungsgrad p von 1,1 bis 3,0 eingesetzt. Aus anwendungstechnischer Sicht sind solche Alkyl- und/oder Alkenyloligoglykoside bevorzugt, deren Oligomerisierungsgrad kleiner als 1 ,7 ist und insbe¬ sondere zwischen 1 ,2 und 1 ,4 liegt.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 oligoglucosides. The index number p in the general formula (V) indicates the degree of oligomerization (DP), i.e. H. the distribution of mono- and oligoglycosides is present and stands for a number between 1 and 10. While p must always be an integer in a given compound and can in particular assume the values p = 1 to 6, the value p is for a specific alkyl oligoglycoside an analytically calculated quantity, which usually represents a fractional number. Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
Der Alkyl- bzw. Alkenylrest R9 kann sich von primären Alkoholen mit 4 bis 11 , vorzugsweise 8 bis 10 Kohlenstoffatomen ableiten. Typische Beispiele sind Butanol, Capronalkohol, Caprylalkohol, Caprinal- kohol und Undecylalkohol sowie deren technische Mischungen, wie sie beispielsweise bei der Hy¬ drierung von technischen Fettsäuremethylestern oder im Verlauf der Hydrierung von Aldehyden aus der Roelen'schen Oxosynthese erhalten werden. Bevorzugt sind Alkyloligoglucoside der Kettenlänge Cβ- C10 (DP = 1 bis 3), die als Vorlauf bei der destillativen Auftrennung von technischem Cβ-Ciβ-Kokosfett- alkohol anfallen und mit einem Anteil von weniger als 6 Gew.-% Cι2-Alkohol verunreinigt sein können sowie Alkyloligoglucoside auf Basis technischer Cg/n-Oxoalkohole {DP = 1 bis 3). Der Alkyl- bzw. Alkenylrest R9 kann sich ferner auch von primären Alkoholen mit 12 bis 22, vorzugsweise 12 bis 14 Kohlenstoffatomen ableiten. Typische Beispiele sind Laurylalkohol, Myristylalkohol, Cetylalkohol, Palm- oleylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, Arachyl- alkohol, Gadoleylalkohol, Behenylalkohol, Erucylalkohol, Brassidylalkohol sowie deren technische Gemische, die wie oben beschrieben erhalten werden können. Bevorzugt sind Alkyloligoglucoside auf Basis von gehärtetem Ci∑yu-Kokosalkohol mit einem DP von 1 bis 3.The alkyl or alkenyl radical R 9 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 from Roelen's oxosynthesis, for example in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes. Alkyl oligoglucosides of chain length Cβ-C10 (DP = 1 to 3) are preferred, which are obtained as a preliminary step in the separation of technical Cβ-Ciβ-coconut fatty alcohol by distillation and contaminated with a proportion of less than 6% by weight of C 2 alcohol can be as well as alkyl oligoglucosides based on technical Cg / n-oxo alcohols {DP = 1 to 3). The alkyl or alkenyl radical R 9 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, palm oleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and the technical mixtures described above, which can be obtained as well as their technical mixtures. Alkyl oligoglucosides based on hydrogenated Ci∑yu coconut alcohol with a DP of 1 to 3 are preferred.
Fettsäure-N-alkylpolyhydroxyalkylamideFatty acid N-alkyl polyhydroxyalkylamides
Fettsäure-N-alkylpolyhydroxyalkylamide, die als Komponente (c2) in Frage kommen, stellen nichtionische Tenside dar, die der Formel (VI) folgen,Fatty acid N-alkylpolyhydroxyalkylamides which are suitable as component (c2) are nonionic surfactants which follow the formula (VI)
I R1°CO-N-[Z] (VI)IR 1 ° CO-N- [Z] (VI)
in der R10CO für einen aliphatischen Acylrest mit 6 bis 22 Kohlenstoffatomen, R11 für Wasserstoff, einen Alkyl- oder Hydroxyalkylrest mit 1 bis 4 Kohlenstoffatomen und [Z] für einen linearen oder verzweigten Polyhydroxyalkylrest mit 3 bis 12 Kohlenstoffatomen und 3 bis 10 Hydroxylgruppen steht. Bei den Fettsäure-N-alkylpolyhydroxyalkylamiden handelt es sich um bekannte Stoffe, die üb¬ licherweise durch reduktive Aminierung eines reduzierenden Zuckers mit Ammoniak, einem Alkylamin oder einem Alkanolamin und nachfolgende Acylierung mit einer Fettsäure, einem Fettsäurealkylester oder einem Fettsäurechlorid erhalten werden können. Hinsichtlich der Verfahren zu ihrer Herstellung sei auf die US-Patentschriften US 1,985,424, US 2,016,962 und US 2,703,798 sowie die Internationale Patentanmeldung WO 92/06984 verwiesen. Eine Übersicht zu diesem Thema von H.Kelkenberg findet sich in Tens.Surf.Deterg. 25, 8 (1988). Vorzugsweise leiten sich die Fettsäure-N-alkylpolyhydroxyalkylamide von reduzierenden Zuckern mit 5 oder 6 Kohlenstoffatomen, insbesondere von der Glucose ab. Die bevorzugten Fettsäure-N-alkyl- polyhydroxyalkylamide stellen daher Fettsäure-N-alkylglucamide dar, wie sie durch die Formel (VII) wiedergegeben werden:in which R 10 CO for an aliphatic acyl radical with 6 to 22 carbon atoms, R 11 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. With regard to the processes for their production, reference is made to US Pat. Nos. 1,985,424, 2,016,962 and 2,703,798 and international patent application WO 92/06984. An overview of this topic by H.Kelkenberg can be found in Tens.Surf.Deterg. 25, 8 (1988). The fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose. The preferred fatty acid N-alkyl polyhydroxyalkylamides are therefore fatty acid N-alkylglucamides, as represented by the formula (VII):
R" OH OH OHR "OH OH OH
I ! I II! I I
Ri°CO-N-CH2.CH-CH-CH-CH-CH2OH (VII)Ri ° CO-N-CH 2 .CH-CH-CH-CH-CH 2 OH (VII)
II.
OHOH
Vorzugsweise werden als Fettsäure-N-alkylpolyhydroxyalkylamide Glucamide der Formel (VII) einge¬ setzt, in der R11 für Wasserstoff oder eine Alkylgruppe steht und R10CO für den Acylrest der Capron- säure, Caprylsäure, Caprinsäure, Laurinsäure, Myristinsäure, Palmitinsäure, Palmoleinsäure, Stearin¬ säure, Isostearinsäure, Ölsäure, Elaidinsäure, Petroselinsäure, Linolsäure, Linolensäure, Arachinsäure, Gadoleinsäure, Behensäure oder Erucasäure bzw. derer technischer Mischungen steht. Besonders bevorzugt sind Fettsäure-N-alkylglucamide der Formel (VII), die durch reduktive Aminierung von Glucose mit Methylamin und anschließende Acylierung mit Laurinsäure oder Ci∑m-Kokosfettsäure bzw. einem entsprechenden Derivat erhalten werden. Weiterhin können sich die Polyhydroxyalkylamide auch von Maltose und Palatinose ableiten.The fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (VII) in which R 11 is hydrogen or an alkyl group and R 10 CO is the acyl radical of capric 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, behenic acid or erucic acid or their technical mixtures. Fatty acid N-alkylglucamides of the formula (VII) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or Ci∑m coconut fatty acid or a corresponding derivative are particularly preferred. Furthermore, the polyhydroxyalkylamides can also be derived from maltose and palatinose.
Die erfindungsgemäßen Zubereitungen können die Komponenten (a) und (b) im Gewichtsverhältnis 10 : 90 bis 90 : 10, vorzugsweise 25 : 75 bis 75 : 25 und insbesondere 40 : 60 bis 60 : 40 enthalten. Wer¬ den ternäre Mischungen eingesetzt, so kann das Gewichtsverhältnis zwischen den Komponenten (b) und (c) ebenfalls wieder 10 : 90 bis 90 : 10, vorzugsweise 25 : 75 bis 75 : 25 und insbesondere 40 : 60 bis 60 : 40 betragen.The preparations according to the invention can contain components (a) and (b) in a weight ratio of 10:90 to 90:10, preferably 25:75 to 75:25 and in particular 40:60 to 60:40. If ternary mixtures are used, the weight ratio between components (b) and (c) can also again be 10:90 to 90:10, preferably 25:75 to 75:25 and in particular 40:60 to 60:40.
FettalkoholeFatty alcohols
In einer besonderen Ausführungsform der Erfindung enthalten die kosmetischen Zubereitungen die Esterquats in Abmischung mit Fettalkoholen der Formel (VIII),In a particular embodiment of the invention, the cosmetic preparations contain the esterquats in admixture with fatty alcohols of the formula (VIII),
R12OH (VIII) in der R12 für einen linearen oder verzweigten, gesättigten oder ungesättigten Kohlenwasserstoffrest mit 6 bis 22, vorzugsweise 12 bis 18 Kohlenstoffatomen steht. Vorzugsweise werden die Esterquats und die Fettalkohole im Gewichtsverhältnis 10 : 90 bis 90 ; 10 und insbesondere 25 : 75 bis 75 : 25 eingesetzt. Die beiden Komponenten können nachträglich abgemischt werden, vorzugsweise werden sie jedoch hergestellt, indem man die den Esterquats zugrundeliegenden Fettsäurealkanolaminester in Fettalkoholen als inertem Lösungsmittel mit Dimethylsulfat quaterniert, wie dies beispielsweise in der Deutschen Patentschrift DE-C1 43 08 794 (Henkel) beschrieben ist. Entsprechende Gemische sind beispielsweise unter der Marke Dehyquart® F im Handel.R 12 OH (VIII) in which R 12 represents a linear or branched, saturated or unsaturated hydrocarbon radical having 6 to 22, preferably 12 to 18, carbon atoms. The esterquats and the fatty alcohols are preferably in a weight ratio of 10:90 to 90; 10 and in particular 25: 75 to 75: 25 used. The two components can be mixed subsequently, but they are preferably prepared by quaternizing the fatty acid alkanolamine esters on which the esterquats are based in fatty alcohols as an inert solvent with dimethyl sulfate, as described, for example, in German Patent DE-C1 43 08 794 (Henkel). Corresponding mixtures are commercially available, for example, under the Dehyquart® F brand.
Gewerbliche AnwendbarkeitIndustrial applicability
Die erfindungsgemäßen Zubereitungen können zur Herstellung von Haut- und Haarbehandlungsmittel eingesetzt werden. Im einfachsten Fall reicht es dazu aus, die Mischungen mit Wasser auf eine Anwendungskonzentration zu verdünnen. Die Mittel, wie beispielsweise Cremes, Lotionen, Haarsham- poos, Haarlotionen, Schaumbäder und dergleichen, können aber ferner als weitere Hilfs- und Zusatzstoffe Ölkörper, Emulgatoren, Überfettungsmittel, Fette, Wachse, Stabilisatoren, Konsistenz¬ geber, Verdickungsmittel, Kationpolymere, biogene Wirkstoffe, Filmbildner, Konservierungsmittel, Farb- und Duftstoffe enthalten.The preparations according to the invention can be used for the production of skin and hair treatment compositions. In the simplest case, it is sufficient to dilute the mixtures with water to an application concentration. The agents, such as, for example, creams, lotions, hair shampoos, hair lotions, bubble baths and the like, can furthermore, as further auxiliaries and additives, oil bodies, emulsifiers, superfatting agents, fats, waxes, stabilizers, consistency agents, thickeners, cation polymers, biogenic active substances , Film formers, preservatives, dyes and fragrances.
Eine typische erfindungsgemäße Zubereitung weist folgende Zusammensetzung auf:A typical preparation according to the invention has the following composition:
10 bis 30, vorzugsweise 20 bis 25 Gew.-% Komponente (a), 1 bis 40, vorzugsweise 10 bis 20 Gew.-% Komponente (b), 1 bis 40, vorzugsweise 15 bis 35 Gew.-% Komponente (c) und 0 bis 80, vorzugsweise 20 bis 75 Gew.-% Fettalkohole10 to 30, preferably 20 to 25% by weight of component (a), 1 to 40, preferably 10 to 20% by weight of component (b), 1 to 40, preferably 15 to 35% by weight of component (c) and 0 to 80, preferably 20 to 75% by weight fatty alcohols
Als Ölkörper kommen beispielsweise Guerbetalkohole auf Basis von Fettalkoholen mit 6 bis 18, vor¬ zugsweise 8 bis 10 Kohlenstoff atomen, Ester von linearen C6-C2o-Fettsäuren mit linearen C6-C2o- Fettalkoholen, Ester von verzweigten C6-Ci3-Carbonsäuren mit linearen C6-C2o-Fettalkoholen, Ester von linearen Cβ-Ciβ-Fettsäuren mit verzweigten Alkoholen, insbesondere 2-Ethylhexanol, Ester von linearen und/oder verzweigten Fettsäuren mit mehrwertigen Alkoholen (wie z.B. Dimerdiol oder Trimer- triol) und/oder Guerbetalkoholen, Triglyceride auf Basis C6-Cιo-Fettsäuren, pflanzliche Öle, verzweigte primäre Alkohole, substituierte Cyclohexane, Guerbetcarbonate, Dialkylether und/oder aliphatische bzw. naphthenische Kohlenwasserstoffe in Betracht. Als Emulgatoren bzw. Co-Emulgatoren können nichtionogene, ampholytische und/oder zwitter¬ ionische grenzflächenaktive Verbindungen verwendet werden, die sich durch eine lipophile, bevorzugt lineare Alkyl- oder Alkenylgruppe und mindestens eine hydrophile Gruppe auszeichnen. Diese hydro¬ phile Gruppe kann sowohl eine ionogene als auch eine nichtionogene Gruppe sein. Nichtionogene Emulgatoren enthalten als hydrophile Gruppe z. B. eine Polyolgruppe, eine Polyalkylenglycolether- gruppe oder eine Kombination aus Polyol- und Polyglycolethergruppe.Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C 2 o-fatty acids with linear C6-C 2 o-fatty alcohols, esters of branched C6-Ci3- Carboxylic acids with linear C6-C2o fatty alcohols, esters of linear Cβ-Ciβ fatty acids with branched alcohols, especially 2-ethylhexanol, esters of linear and / or branched fatty acids with polyhydric alcohols (such as dimer diol or trimer triol) and / or Guerbet alcohols , Triglycerides based on C6-Cιo fatty acids, vegetable oils, branched primary alcohols, substituted cyclohexanes, Guerbet carbonates, dialkyl ethers and / or aliphatic or naphthenic hydrocarbons. Nonionic, ampholytic and / or zwitterionic surface-active compounds which are distinguished by a lipophilic, preferably linear alkyl or alkenyl group and at least one hydrophilic group can be used as emulsifiers or co-emulsifiers. This hydrophilic group can be both an ionogenic and a nonionic group. Non-ionic emulsifiers contain as a hydrophilic group z. B. a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
Bevorzugt sind solche Mittel, die als O/W-Emulgatoren nichtionogene Tenside aus mindestens einer der folgenden Gruppen enthalten:Preferred agents are those which contain nonionic surfactants from at least one of the following groups as O / W emulsifiers:
(a1) Anlagerungsprodukte von 2 bis 30 Mol Ethylenoxid und/ oder 0 bis 5 Mol Propylenoxid an lineare(a1) Addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide onto linear ones
Fettalkohole mit 8 bis 22 C-Atomen, an Fettsäuren mit 12 bis 22 C-Atomen und an Alkylphenole mit 8 bis 15 C-Atomen in der Alkylgruppe; (a2) Ci2/i8-Fettsäuremono- und -diester von Anlagerungsprodukten von 1 bis 30 Mol Ethylenoxid anFatty alcohols with 8 to 22 carbon atoms, on fatty acids with 12 to 22 carbon atoms and on alkylphenols with 8 to 15 carbon atoms in the alkyl group; (a2) Ci2 / i8 fatty acid monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide
Glycerin; (a3) Glycerinmono- und -diester und Sorbitanmono- und -diester von gesättigten und ungesättigtenGlycerin; (a3) Glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated
Fettsäuren mit 6 bis 22 Kohlenstoffatomen und deren Ethylenoxidanlagerungsprodukte; (a4) Alkylmono- und -oligoglycoside mit 8 bis 22 Kohlenstoffatomen im Alkylrest und deren ethoxy- lierte Analoga; (a5) Anlagerungsprodukte von 15 bis 60 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl; (a6) Polyol- und insbesondere Polyglycerinester wie z.B. Polyglycerinpolyricinoleat oder Polyglyce- rinpoly-12-hydroxystearat. Ebenfalls geeignet sind Gemische von Verbindungen aus mehreren dieser Substanzklassen.Fatty acids with 6 to 22 carbon atoms and their ethylene oxide addition products; (a4) alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs; (a5) adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil; (a6) polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricinoleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable.
Die Anlagerungsprodukte von Ethylenoxid und/oder von Propylenoxid an Fettalkohole, Fettsäuren, Alkylphenole, Glycerinmono- und -diester sowie Sorbitanmono- und -diester von Fettsäuren oder an Ricinusöl stellen bekannte, im Handel erhältliche Produkte dar. Es handelt sich dabei um Homo¬ logengemische, deren mittlerer Alkoxylierungsgrad dem Verhältnis der Stoffmengen von Ethylenoxid und/oder Propylenoxid und Substrat, mit denen die Anlagerungsreaktion durchgeführt wird, entspricht. Ci2/i8-Fettsäuremono- und -diester von Anlagerungsprodukten von Ethylenoxid an Glycerin sind aus DE-PS 20 24 051 als Rückfettungsmittel für kosmetische Zubereitungen bekannt.The adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are homogeneous mixtures, whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out. Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.
Weiterhin können als Emulgatoren zwitterionische Tenside verwendet werden. Als zwitterionische Tenside werden solche oberflächenaktiven Verbindungen bezeichnet, die im Molekül mindestens eine quartäre Ammoniumgruppe und mindestens eine Carboxylat- und eine Sulfonatgruppe tragen. Besonders geeignete zwitterionische Tenside sind die sogenannten Betaine wie die N-Alkyl-N,N- dimethylammoniumglycinate, beispielsweise das Kokosalkyldimethylammoniumglycinat, N-Acylamino- propyl-N,N-dimethylammoniumglycinate, beispielsweise das Kokosacylaminopropyldimethylammonium- glycinat, und 2-Alkyl-3-carboxylmethyl-3-hydroxyethylimidazoline mit jeweils 8 bis 18 C-Atomen in der Alkyl- oder Acylgruppe sowie das Kokosacylaminoethylhydroxyethylcarboxymethylglycinat. Besonders bevorzugt ist das unter der CTFA-Bezeichnung Cocamidopropyl Betaine bekannte Fettsäureamid- Derivat. Ebenfalls geeignete Emulgatoren sind ampholytische Tenside. Unter ampholytischen Tensiden werden solche oberflächenaktiven Verbindungen verstanden, die außer einer Cβπβ-Alkyl- oder -Acyl¬ gruppe im Molekül mindestens eine freie Aminogruppe und mindestens eine -COOH- oder -SO3H- Gruppe enthalten und zur Ausbildung innerer Salze befähigt sind. Beispiele für geeignete ampholytische Tenside sind N-Alkylglycine, N-Alkylpropionsäuren, N-Alkylaminobuttersäuren, N- Alkyliminodipropionsäuren, N-Hydroxyethyl-N-alkylamidopropylglycine, N-Alkyltaurine, N-Alkylsarco- sine, 2-Alkylaminopropionsäuren und Alkylaminoessigsäuren mit jeweils etwa 8 bis 18 C-Atomen in der Alkylgruppe. Besonders bevorzugte ampholytische Tenside sind das N-Kokosalkylaminopropionat, das Kokosacylaminoethylaminopropionat und das Ci2/i6-Acylsarcosin.Zwitterionic surfactants can also be used as emulsifiers. Zwitterionic surfactants are those surface-active compounds that contain at least one in the molecule carry quaternary ammonium group and at least one carboxylate and one sulfonate group. Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate. The fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred. Suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a Cβπβ-alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / i6-acylsarcosine.
Als W/O-Emulgatoren kommen in Betracht:W / O emulsifiers are:
(b1) Anlagerungsprodukte von 2 bis 15 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl;(b1) adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil;
(b2) Partialester auf Basis linearer, verzweigter, ungesättigter bzw. gesättigter Ci2/22-Fettsäuren, Ricinolsäure sowie 12-Hydroxystearinsäure und Glycerin, Polyglycerin, Pentaerythrit, Dipenta- erythrit, Zuckeralkohole (z.B. Sorbit) sowie Polyglucoside (z.B. Cellulose);(b2) partial esters based on linear, branched, unsaturated or saturated Ci2 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol) and polyglucosides (e.g. cellulose);
(b3) Trialkylphosphate;(b3) trialkyl phosphates;
(b4) Wollwachsalkohole;(b4) wool wax alcohols;
(b5) Polysiloxan-Polyalkyl-Polyether-Copolymere bzw. entsprechende Derivate;(b5) polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives;
(b6) Mischester aus Pentaerythrit, Fettsäuren, Citronensäure und Fettalkohol gemäß DE-PS 11 65 574 sowie(b6) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE-PS 11 65 574 and
(b7) Polyalkylenglycole.(b7) polyalkylene glycols.
Als Überfettungsmittel können Substanzen wie beispielsweise polyethoxylierte Lanolinderivate, Lecithinderivate, Polyolfettsäureester, Monoglyceride und Fettsäurealkanolamide verwendet werden, wobei die letzteren gleichzeitig als Schaumstabilisatoren dienen. Typische Beispiele für Fette sind Glyceride, als Wachse kommen u.a. Bienenwachs, Paraffinwachs oder Mikrowachse gegebenenfalls in Kombination mit hydrophilen Wachsen, z.B. Cetylstearylalkohol in Frage. Als Stabilisatoren können Metallsalze von Fettsäuren wie z.B. Magnesium-, Aluminium- und/oder Zinkstearat eingesetzt werden. Als Konsistenzgeber kommen in erster Linie wiederum Fettalkohole mit 12 bis 22 und vorzugsweise 16 bis 18 Kohlenstoffatomen in Betracht. Bevorzugt ist eine Kombination dieser Stoffe mit Alkyloligoglucosiden und/oder Fettsäure-N-methylglucamiden gleicher Kettenlänge und/oder Poly- glycerinpoly-12-hydroxystearaten. Geeignete Verdickungsmittel sind beispielsweise Polysaccharide, insbesondere Xanthan-Gum, Guar-Guar, Agar-Agar, Alginate und Tylosen, Carboxymethylcellulose und Hydroxyethylcellulose, ferner höhermolekulare Polyethylenglycolmono- und -diester von Fettsäu¬ ren, Polyacrylate, Polyvinylalkohol und Polyvinylpyrrolidon, Tenside wie beispielsweise Fettalkohol- ethoxylate mit eingeengter Homologenverteilung oder Alkyloligoglucoside sowie Elektrolyte wie Kochsalz und Ammoniumchlorid.Substances such as polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers. Typical examples of fats are glycerides; beeswax, paraffin wax or microwaxes may be used as waxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol. Can be used as stabilizers Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used. Fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms are primarily considered as consistency agents. A combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred. Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, furthermore higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as table salt and ammonium chloride.
Geeignete kationische Polymere sind beispielsweise kationischen Cellulosederivate, kationischen Stärke, Copolymere von Diallylammoniumsalzen und Acrylamiden, quatemierte Vinylpyrrolidon/Vinyl- imidazol-Polymere wie z.B. Luviquat® (BASF AG, Ludwigshafen/ FRG), Kondensationsprodukte von Polyglycolen und Aminen, quatemierte Kollagenpolypeptide wie beispielsweise Lauryldimonium hydroxypropyl hydrolyzed collagen (LamequatΘL, Grünau GmbH), quatemierte Weizenpolypeptide,Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as e.g. Luviquat® (BASF AG, Ludwigshafen / FRG), condensation products of polyglycols and amines, quaternized collagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen (LamequatΘL, Grünau GmbH), quaternized wheat polypeptides,
Polyethylenimin, kationische Siliconpolymere wie z.B. Amidomethicone oder Dow Corning, Dow Cor¬ ning Co./US, Copolymere der Adipinsäure und Dimethylaminohydroxypropyldiethylentrimamin (Carta- retine®, Sandoz/CH), Polyaminopolyamide wie z.B. beschrieben in der FR-A 22 52 840 sowie deren vernetzte wasserlöslichen Polymere, kationische Chitinderivate wie beispielsweise quaterniertes Chito- san, gegebenenfalls mikrokristallin verteilt, kationischer Guar-Gum wie z.B. Jaguar® CBS, Jaguar® C- 17, Jaguar® C-16 der Celanese/US, quatemierte Ammoniumsalz-Polymere wie z.B. Mirapol® A-15, Mirapol® AD-1 , Mirapol® AZ-1 der Miranol/US.Polyethyleneimine, cationic silicone polymers such as e.g. Amidomethicone or Dow Corning, Dow Coring Co./US, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetrimamine (Carretine®, Sandoz / CH), polyaminopolyamides such as e.g. described in FR-A 22 52 840 and its crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, cationic guar gum such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese / US, quaternized ammonium salt polymers such as Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol / US.
Unter biogenen Wirkstoffen sind beispielsweise Pflanzenextrakte und Vitaminkomplexe zu verstehen. Als Antischuppenmittel kommt beispielsweise Octopirox in Frage. Gebräuchliche Filmbildner sind beispielsweise Chitosan, mikrokristallines Chitosan, quaterniertes Chitosan, Polyvinylpyrrolidon, Vinyl- pyrrolidon-Vinylacetat-Copolymerisate, Polymere der Acrylsäurereihe, quaternäre Cellulose-Derivate, Kollagen, Hyaluronsäure bzw. deren Salze und ähnliche Verbindungen. Als Konservierungsmittel eignen sich beispielsweise Phenoxyethanol, Formaldehydlösung, Parabene, Pentandiol oder Sorbin¬ säure. Als Perlglanzmittel kommen beispielsweise Glycoldistearinsäureester wie Ethylenglycol- distearat, aber auch Fettsäuremonoglycolester in Betracht. Als Farbstoffe können die für kosmetische Zwecke geeigneten und zugelassenen Substanzen verwendet werden, wie sie beispielsweise in der Publikation "Kosmetische Färbemittel" der Farbstoffkommission der Deutschen Forschungsge¬ meinschaft, Verlag Chemie, Weinheim, 1984, S.81-106 zusammengestellt sind. Diese Farbstoffe werden üblicherweise in Konzentrationen von 0,001 bis 0,1 Gew.-%, bezogen auf die gesamte Mi¬ schung, eingesetzt.Biogenic active substances are understood to mean, for example, plant extracts and vitamin complexes. For example, octopirox can be used as an antidandruff agent. Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds. Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid. Suitable pearlizing agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters. The dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes" by the Dye Commission of the German Research Foundation, 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 total mixture.
Der Gesamtanteil der Hilfs- und Zusatzstoffe kann 1 bis 50, vorzugsweise 5 bis 40 Gew.-% - bezogen auf die Mittel - betragen. The total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
BeispieleExamples
Es wurden Konzentrate der Zusammensetzung gemäß Tabelle 1 hergestellt:Concentrates of the composition according to Table 1 were produced:
Tabelle 1 Erfindungsgemäße Konzentrate (Zusammensetzung in Gew.-%)Table 1 Concentrates according to the invention (composition in% by weight)
Figure imgf000016_0001
Figure imgf000016_0001
Jeweils 5 g der Konzentrate K1 bis K5 wurden mit 95 g warmen Wasser verdünnt. Es entstanden nie¬ drigviskose Emulsionen, die sich auch bei einer Lagerung von 4 Wochen bei 40°C als stabil erwiesen.5 g of the concentrates K1 to K5 were diluted with 95 g of warm water. Low viscosity emulsions were formed which proved to be stable even when stored for 4 weeks at 40 ° C.
Jeweils 4 g der Konzentrate wurden mit 25 g Plantaren® PS 10 (einer Mischung aus einem Lauryl- oligoglucosid und einem Fettalkoholethersulfat) vermischt und mit 69 ml Wasser verdünnt. Den Lö¬ sungen wurden zur Einstellung der Viskosität 2 g Kochsalz zugesetzt. Den 5 erfindungsgemäßen Shampoos wurde ein Produkt gegenübergestellt, welches 25 Gew.-% Plantaren® PS 10, 4 Gew.-%4 g of the concentrates were mixed with 25 g of Plantaren® PS 10 (a mixture of a lauryl oligoglucoside and a fatty alcohol ether sulfate) and diluted with 69 ml of water. To adjust the viscosity, 2 g of sodium chloride were added to the solutions. The 5 shampoos according to the invention were compared with a product which 25% by weight of Plantaren® PS 10, 4% by weight
Esterquat, 2 Gew.-% g Kochsalz und ad 100 Gew.-% Wasser enthielt. Alle 6 Shampoos wurden von einem Panel bestehend aus 10 geschulten Probanden beurteilt. Dabei wurde jedes der 5 erfindungsge¬ mäßen Produkte bezüglich des Weichgriffs der Haare um mindestens 20 % besser als das Vergleichs¬ produkt beurteilt. Esterquat, 2 wt .-% g of sodium chloride and ad 100 wt .-% water. All 6 shampoos were assessed by a panel consisting of 10 trained subjects. Each of the 5 products according to the invention was rated at least 20% better than the comparative product with regard to the softness of the hair.

Claims

Patentansprüche claims
1. Kosmetische Zubereitungen, enthaltend (a) Esterquats und1. Cosmetic preparations containing (a) esterquats and
(b1) Sorbitanester,(b1) sorbitan esters,
(b2) Polyotpoly-12-hydroxystearate und/oder(b2) Polyotpoly-12-hydroxystearate and / or
(b3) Glyceride sowie gegebenenfalls(b3) glycerides and optionally
(d ) Alkyl- und/oder Alkenyloligoglykoside und/oder(d) alkyl and / or alkenyl oligoglycosides and / or
(c2) Fettsäure-N-alkylpolyhydroxyalkylamide.(c2) Fatty acid N-alkyl polyhydroxyalkyl amides.
2. Zubereitungen nach Anspruch 1 , dadurch gekennzeichnet, daß sie Esterquats der Formel (I) enthalten,2. Preparations according to claim 1, characterized in that they contain ester quats of the formula (I),
R4 R 4
I [R1CO.(OCH2CH2)mOCH2CH2-N+-CH2CH20-(CH2CH20)nR2] X- (I)I [R 1 CO. (OCH 2 CH 2 ) mOCH 2 CH 2 -N + -CH 2 CH 2 0- (CH 2 CH 2 0) n R 2 ] X- (I)
I CH2CH20(CH2CH20)PR3 I CH 2 CH 2 0 (CH 2 CH 2 0) P R 3
in der R1CO für einen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 und R3 unabhängig voneinander für Wasserstoff oder R1CO, R4 für einen Alkylrest mit 1 bis 4 Kohlenstoffatomen oder eine (CH2CH20)qH-Gruppe, m, n und p in Summe für 0 oder Zahlen von 1 bis 12, q für Zahlen von 1 bis 12 und X für Halogenid, Alkylsulfat oder Alkylphosphat steht.in which R 1 CO for an acyl radical having 6 to 22 carbon atoms, R 2 and R 3 independently of one another for hydrogen or R 1 CO, R 4 for an alkyl radical with 1 to 4 carbon atoms or a (CH 2 CH 2 0) q H- Group, m, n and p in total stands for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate.
3. Zubereitungen nach Anspruch 2, dadurch gekennzeichnet, daß sie Esterquats der Formel (II) enthalten,3. Preparations according to claim 2, characterized in that they contain ester quats of the formula (II),
R4 R 4
I [R1CO-(OCH2CH2)mOCH2CH2-N+-CH2CH2θ-(CH2CH20)nR2] X- (II)
Figure imgf000017_0001
I [R 1 CO- (OCH 2 CH2) mOCH2CH2-N + -CH2CH2θ- (CH2CH 2 0) n R 2 ] X- (II)
Figure imgf000017_0001
in der R1CO für einen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 für Wasserstoff oder R1C0, R4 und R5 unabhängig voneinander für Alkylreste mit 1 bis 4 Kohlenstoff atomen, m und n in Summe für 0 oder Zahlen von 1 bis 12 und X für Halogenid, Alkylsulfat oder Alkylphosphat steht. 1 CO is an acyl group containing 6 to 22 carbon atoms, R 2 is hydrogen or R 1 C0, R 4 and R 5 atoms in the R independently of one another are alkyl groups containing 1 to 4 carbon atoms, m and n together stand for 0 or numbers of 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate.
4. Zubereitungen nach Anspruch 3, dadurch gekennzeichnet, daß sie Esterquats der Formel (III) enthalten,4. Preparations according to claim 3, characterized in that they contain ester quats of the formula (III),
[R4-
Figure imgf000018_0001
nR2] X" (III)
[R 4 -
Figure imgf000018_0001
nR 2 ] X "(III)
II.
R'R '
in der R1C0 für einen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 für Wasserstoff oder R1CO, R4, R6 und R7 unabhängig voneinander für Alkylreste mit 1 bis 4 Kohlenstoffatomen, m und n in Summe für 0 oder Zahlen von 1 bis 12 und X für Halogenid, Alkylsulfat oder Alkylphosphat steht.in which R 1 is C0 for an acyl radical with 6 to 22 carbon atoms, R 2 for hydrogen or R 1 CO, R 4 , R 6 and R 7 independently of one another for alkyl radicals with 1 to 4 carbon atoms, m and n in total for 0 or numbers from 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate.
5. Zubereitungen nach den Ansprüchen 1 bis 4, dadurch gekennzeichnet, daß sie als Komponente (b1) Sorbitanester der Formel (IV) enthalten,5. Preparations according to claims 1 to 4, characterized in that they contain sorbitan esters of the formula (IV) as component (b1),
Figure imgf000018_0002
Figure imgf000018_0002
in der R8CO für einen aliphatischen, gesättigten oder ungesättigten Acylrest mit 6 bis 22 und vorzugsweise 12 bis 18 Kohlenstoffatomen steht.in which R 8 CO represents an aliphatic, saturated or unsaturated acyl radical having 6 to 22 and preferably 12 to 18 carbon atoms.
6. Zubereitungen nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet, daß sie als Komponente (b2) Polyglycerinpoly-12-hydroxystearate enthalten.6. Preparations according to claims 1 to 5, characterized in that they contain as component (b2) polyglycerol poly-12-hydroxystearate.
7. Zubereitungen nach den Ansprüchen 1 bis 6, dadurch gekennzeichnet, daß sie als Komponente (b3) technische Partialglyceride auf Basis von Fettsäuren mit 12 bis 18 Kohlenstoffatomen enthalten.7. Preparations according to claims 1 to 6, characterized in that they contain as component (b3) technical partial glycerides based on fatty acids with 12 to 18 carbon atoms.
8. Zubereitungen nach den Ansprüchen 1 bis 7, dadurch gekennzeichnet, daß sie als Komponente (d) Alkyl- und Alkenyloligoglykoside der Formel (V) enthalten,8. Preparations according to claims 1 to 7, characterized in that they contain as component (d) alkyl and alkenyl oligoglycosides of the formula (V),
R90-[G]P (V) in der R1 für einen Alkyl- und/oder Alkenylrest mit 4 bis 22 Kohlenstoffatomen, G für einen Zuckerrest mit 5 oder 6 Kohlenstoffatomen und p für Zahlen von 1 bis 10 steht.R 9 0- [G] P (V) 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.
9. Zubereitungen nach den Ansprüchen 1 bis 8, dadurch gekennzeichnet, daß sie als Komponente (c2) Fettsäure-N-alkylpolyhydroxyalkylamide der Formel (VI) enthalten,9. Preparations according to claims 1 to 8, characterized in that they contain as component (c2) fatty acid-N-alkylpolyhydroxyalkylamides of the formula (VI),
II.
R1°CO-N-[Z] (VI)R 1 ° CO-N- [Z] (VI)
in der R10CO für einen aliphatischen Acylrest mit 6 bis 22 Kohlenstoffatomen, R11 für Wasserstoff, einen Alkyl- oder Hydroxyalkylrest mit 1 bis 4 Kohlenstoffatomen und [Z] für einen linearen oder verzweigten Polyhydroxyalkylrest mit 3 bis 12 Kohlenstoffatomen und 3 bis 10 Hydroxylgruppen steht.in which R 10 CO for an aliphatic acyl radical with 6 to 22 carbon atoms, R 11 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.
10. Zubereitungen nach den Ansprüchen 1 bis 9, dadurch gekennzeichnet, daß sie als weitere Komponente Fettalkohole der Formel (VIII) enthalten,10. Preparations according to claims 1 to 9, characterized in that they contain fatty alcohols of the formula (VIII) as a further component,
R12OH (VIII)R 12 OH (VIII)
in der R12 für einen linearen oder verzweigten, gesättigten oder ungesättigten Kohlenwasserstoff¬ rest mit 6 bis 22, vorzugsweise 12 bis 18 Kohlenstoffatomen steht. in which R 12 represents a linear or branched, saturated or unsaturated hydrocarbon radical having 6 to 22, preferably 12 to 18, carbon atoms.
PCT/EP1997/002898 1996-06-14 1997-06-04 Cosmetic preparations based on cationic and non ionic surfactants WO1997047284A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP97928146A EP0910338A1 (en) 1996-06-14 1997-06-04 Cosmetic preparations based on cationic and non ionic surfactants
JP10501151A JP2000512286A (en) 1996-06-14 1997-06-04 Cosmetic formulations containing cationic and nonionic surfactants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1996123763 DE19623763C2 (en) 1996-06-14 1996-06-14 Cosmetic preparations
DE19623763.7 1996-06-14

Publications (1)

Publication Number Publication Date
WO1997047284A1 true WO1997047284A1 (en) 1997-12-18

Family

ID=7796956

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1997/002898 WO1997047284A1 (en) 1996-06-14 1997-06-04 Cosmetic preparations based on cationic and non ionic surfactants

Country Status (4)

Country Link
EP (1) EP0910338A1 (en)
JP (1) JP2000512286A (en)
DE (1) DE19623763C2 (en)
WO (1) WO1997047284A1 (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999038477A1 (en) * 1998-01-31 1999-08-05 Cognis Deutschland Gmbh Method for permanently deforming keratin fibers
DE19805703A1 (en) * 1998-02-06 1999-08-12 Henkel Kgaa Hair care products
DE19851451A1 (en) * 1998-11-09 2000-05-11 Cognis Deutschland Gmbh Cosmetic and / or pharmaceutical preparations
WO2013178701A2 (en) 2012-05-30 2013-12-05 Clariant International Ltd. Compositions containing fatty alcohols, cationic surfactants and n-acyl-n-methylglucamines
DE202013011413U1 (en) 2013-12-20 2014-01-27 Clariant International Ltd. Conditioning shampoos containing anionic surfactants, glucamides and fatty alcohols
DE202013011412U1 (en) 2013-12-20 2014-01-27 Clariant International Ltd. Glucamide to improve the silicone position
DE102013018001A1 (en) 2013-11-29 2015-06-03 Clariant International Ltd. Use of glucamides to improve the silicone position
DE102013018000A1 (en) 2013-11-29 2015-06-03 Clariant International Ltd. Conditioning shampoos containing anionic surfactants, glucamides and fatty alcohols
US10772324B2 (en) 2012-11-03 2020-09-15 Clariant International Ltd. Aqueous adjuvant-compositions
US10813862B2 (en) 2012-05-30 2020-10-27 Clariant International Ltd. Use of N-methyl-N-acylglucamines as solubilizers
US10864275B2 (en) 2012-05-30 2020-12-15 Clariant International Ltd. N-methyl-N-acylglucamine-containing composition
US10920080B2 (en) 2015-10-09 2021-02-16 Clariant International Ltd. N-Alkyl glucamine-based universal pigment dispersions
US10961484B2 (en) 2015-10-09 2021-03-30 Clariant International Ltd. Compositions comprising sugar amine and fatty acid
US11220603B2 (en) 2016-05-09 2022-01-11 Clariant International Ltd. Stabilizers for silicate paints
US11425904B2 (en) 2014-04-23 2022-08-30 Clariant International Ltd. Use of aqueous drift-reducing compositions

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3888595B2 (en) * 1997-01-30 2007-03-07 三洋化成工業株式会社 Hair treatment agent
DE19810122C2 (en) * 1998-03-09 2000-04-06 Goldwell Gmbh Hair treatment agents
DE69915822T2 (en) 1998-05-20 2005-01-27 Kao Corporation PLASTICISERS COMPOSITION
US6541444B1 (en) 1998-05-20 2003-04-01 Kao Corporation Softener composition
DE19919087C2 (en) * 1999-04-27 2003-02-27 Cognis Deutschland Gmbh Process for permanent deformation of keratin fibers
DE19922229A1 (en) * 1999-05-14 2000-11-16 Cognis Deutschland Gmbh Cosmetic and / or pharmaceutical preparations
JP5202860B2 (en) * 2007-03-26 2013-06-05 株式会社 資生堂 Low viscosity transparent composition with water thickening

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4224714A1 (en) * 1992-07-27 1994-02-03 Henkel Kgaa Foaming detergent mixtures
WO1994006899A1 (en) * 1992-09-11 1994-03-31 Henkel Kommanditgesellschaft Auf Aktien Detergent mixtures
DE4309568A1 (en) * 1993-03-24 1994-09-29 Henkel Kgaa Detergent mixtures with improved softening properties
DE29520748U1 (en) * 1995-11-09 1996-03-14 Henkel KGaA, 40589 Düsseldorf Cosmetic and / or pharmaceutical emulsions
US5562847A (en) * 1995-11-03 1996-10-08 The Procter & Gamble Company Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4224714A1 (en) * 1992-07-27 1994-02-03 Henkel Kgaa Foaming detergent mixtures
WO1994006899A1 (en) * 1992-09-11 1994-03-31 Henkel Kommanditgesellschaft Auf Aktien Detergent mixtures
DE4309568A1 (en) * 1993-03-24 1994-09-29 Henkel Kgaa Detergent mixtures with improved softening properties
US5562847A (en) * 1995-11-03 1996-10-08 The Procter & Gamble Company Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity
DE29520748U1 (en) * 1995-11-09 1996-03-14 Henkel KGaA, 40589 Düsseldorf Cosmetic and / or pharmaceutical emulsions

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999038477A1 (en) * 1998-01-31 1999-08-05 Cognis Deutschland Gmbh Method for permanently deforming keratin fibers
DE19805703A1 (en) * 1998-02-06 1999-08-12 Henkel Kgaa Hair care products
WO1999039690A1 (en) * 1998-02-06 1999-08-12 Cognis Deutschland Gmbh Hair-conditioning agents
DE19805703C2 (en) * 1998-02-06 2001-05-03 Cognis Deutschland Gmbh Hair care products
US6641803B1 (en) 1998-02-06 2003-11-04 Cognis Deutschland Gmbh & Co. Kg Hair-conditioning agents
DE19851451A1 (en) * 1998-11-09 2000-05-11 Cognis Deutschland Gmbh Cosmetic and / or pharmaceutical preparations
WO2013178701A2 (en) 2012-05-30 2013-12-05 Clariant International Ltd. Compositions containing fatty alcohols, cationic surfactants and n-acyl-n-methylglucamines
US10864275B2 (en) 2012-05-30 2020-12-15 Clariant International Ltd. N-methyl-N-acylglucamine-containing composition
US10813862B2 (en) 2012-05-30 2020-10-27 Clariant International Ltd. Use of N-methyl-N-acylglucamines as solubilizers
WO2013178701A3 (en) * 2012-05-30 2014-07-03 Clariant International Ltd. Compositions containing fatty alcohols, cationic surfactants and n-acyl-n-methylglucamines
US10772324B2 (en) 2012-11-03 2020-09-15 Clariant International Ltd. Aqueous adjuvant-compositions
DE102013018000A1 (en) 2013-11-29 2015-06-03 Clariant International Ltd. Conditioning shampoos containing anionic surfactants, glucamides and fatty alcohols
WO2015078586A1 (en) * 2013-11-29 2015-06-04 Clariant International Ltd Conditioning shampoos containing anionic surfactants, glucamides, and fatty alcohols
WO2015078587A1 (en) 2013-11-29 2015-06-04 Clariant International Ltd Use of glucamides to improve silicone deposition
US20170000710A1 (en) * 2013-11-29 2017-01-05 Clariant International Ltd. Conditioning Shampoos Containing Anionic Surfactants, Glucamides, And Fatty Alcohols
DE102013018001A1 (en) 2013-11-29 2015-06-03 Clariant International Ltd. Use of glucamides to improve the silicone position
DE202013011412U1 (en) 2013-12-20 2014-01-27 Clariant International Ltd. Glucamide to improve the silicone position
DE202013011413U1 (en) 2013-12-20 2014-01-27 Clariant International Ltd. Conditioning shampoos containing anionic surfactants, glucamides and fatty alcohols
US11425904B2 (en) 2014-04-23 2022-08-30 Clariant International Ltd. Use of aqueous drift-reducing compositions
US10920080B2 (en) 2015-10-09 2021-02-16 Clariant International Ltd. N-Alkyl glucamine-based universal pigment dispersions
US10961484B2 (en) 2015-10-09 2021-03-30 Clariant International Ltd. Compositions comprising sugar amine and fatty acid
US11220603B2 (en) 2016-05-09 2022-01-11 Clariant International Ltd. Stabilizers for silicate paints

Also Published As

Publication number Publication date
EP0910338A1 (en) 1999-04-28
JP2000512286A (en) 2000-09-19
DE19623763A1 (en) 1998-01-08
DE19623763C2 (en) 1999-08-26

Similar Documents

Publication Publication Date Title
EP0910338A1 (en) Cosmetic preparations based on cationic and non ionic surfactants
EP0914087B1 (en) Use of fats to replace silicone in the production of cosmetic and/or pharmaceutical preparations
DE19805703C2 (en) Hair care products
EP0910329B1 (en) Aqueous nacreous lustre concentrates
EP0941060B1 (en) Cosmetic preparations
DE19732015C1 (en) Self-emulsifying formulation useful in production of cosmetics, e.g. hair conditions
EP0910328B1 (en) Aqueous nacreous lustre concentrate
DE19708133C1 (en) Conditioner for textile and keratin fibres useful as e.g. laundry or hair conditioner
EP0912700B1 (en) Aqueous nacreous lustre concentrates
EP0689531A1 (en) Method of producing solid quaternary esters with improved emulsifying power
DE19651447C1 (en) Textile or hair conditioners having improved performance
EP0821580B1 (en) Hair-treatment agents
DE19725964C1 (en) Fluid, biodegradable aqueous pearlescent concentrate used in surfactant formulation
DE19652300C2 (en) Use of esterquats as emulsifiers for dihydroxyacetone
DE19754283A1 (en) Use of detergent mixtures
EP0830857B1 (en) Cosmetic compositions
DE19724867C1 (en) Use of emulsifier mixtures in pharmaceutical, cosmetic and shampoo compositions
DE19652299C2 (en) Use of ester quats
DE19732709C1 (en) Aqueous pearlescent concentrates
WO1995028143A1 (en) Hair and body care products

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1997928146

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1997928146

Country of ref document: EP

WWR Wipo information: refused in national office

Ref document number: 1997928146

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1997928146

Country of ref document: EP