WO2001035909A1 - Produits de soins capillaires antigras - Google Patents

Produits de soins capillaires antigras Download PDF

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Publication number
WO2001035909A1
WO2001035909A1 PCT/EP2000/010998 EP0010998W WO0135909A1 WO 2001035909 A1 WO2001035909 A1 WO 2001035909A1 EP 0010998 W EP0010998 W EP 0010998W WO 0135909 A1 WO0135909 A1 WO 0135909A1
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WIPO (PCT)
Prior art keywords
hair
formula
groups
hydrogen
monomers
Prior art date
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PCT/EP2000/010998
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German (de)
English (en)
Inventor
Manuela Ehlert
Ulrich Bernecker
Detlef Hollenberg
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO2001035909A1 publication Critical patent/WO2001035909A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • the invention relates to the use of zwitterionic polymers as a component in hair care products for reducing the greasy appearance of the hair.
  • Oily hair is perceived by most people in Central Europe and North America as a cosmetic problem. This manifests itself essentially in the fact that the hair looks streaky and appears to be less voluminous.
  • Greasy hair is difficult to style because the fibers adhere to one another over large areas. So far, greasy-looking hair has been treated with agents that counteract excessive sebum production. Frequent washing and wearing shorter hairstyles have also been recommended to reduce the problems of oily hair. From S ⁇ FW-Journal, 120th volume, 6/1994, page 340-344 it is known that the regreasing of the hair can also be slowed down with an abietic acid-protein condensate.
  • the invention therefore relates to a process for reducing the greasy appearance of the hair by treating the hair with a hair care product in the form of an aqueous preparation which contains a zwitterionic polymer with free carboxyl groups and quaternary ammonium groups dissolved therein.
  • All hair cosmetic preparations which are used in the form of aqueous preparations on the hair can be used as hair care products.
  • Such preparations are e.g. B. hair rinses, hair shampoos, oxidizing dye developers, permanent wave fixatives, hair fixatives, water wave lotions, and other aqueous hair cosmetics.
  • a particularly preferred embodiment of the method therefore consists in rinsing the hair with water after the treatment with the hair care product and after a contact time.
  • preferred hair treatment agents are, in particular, hair rinses, hair treatments and shampoos.
  • Suitable zwitterionic polymers can be obtained either by polymerizing zwitterionic monomers or by copolymerizing cationic monomers with quaternary ammonium groups, unsaturated carboxylic acids and, if appropriate, neutral monomers.
  • a particularly preferred group of zwitterionic polymers consists essentially of monomers with quaternary ammonium groups of the formula I,
  • R'-CH CR 2 -CO-Z- (C n -H 2n ) -N (+) (CH 3 ) 3 A ⁇ (I)
  • R 1 and R 2 are hydrogen or methyl groups
  • Z is an oxygen atom or an NH group.
  • n 2 to 5 and A (“ 'is a chloride, bromide, methoxysulfate or ethoxysulfate anion.
  • R 3 and R 4 are hydrogen or methyl groups and monomers with ester groups of the formula III
  • R 5 -CH CR 6 -COOR 7 (III) in which R 5 and R are hydrogen or methyl groups and R 7 is an alkyl group with 1-4
  • Suitable monomers of formula I are e.g. B .:
  • Methacrylamidopropyl trimethylammonium chloride or acrylic acid trimethylammonioethyl ester chloride are examples of acrylic acid trimethylammonioethyl ester chloride.
  • Suitable monomers of formula II are e.g. B. acrylic acid, methacrylic acid or crotonic acid and suitable monomers of formula III are such. B. ethyl acrylate, butyl methacrylate or
  • Monomers can be contained in the preferably suitable zwitterionic polymers without the effect of delaying the regreasing of the hair suffering. Particularly good effects, especially in delaying the regreasing of the hair, have been found in such
  • the effect of the zwitterionic polymers is achieved not only from aqueous solutions, but from typical aqueous hair-cosmic preparations, such as those used for. B. for the purposes of hair remediation, antistatic treatment, shampooing, setting and for other hair cosmetic tasks.
  • a surfactant content is achieved not only from aqueous solutions, but from typical aqueous hair-cosmic preparations, such as those used for. B. for the purposes of hair remediation, antistatic treatment, shampooing, setting and for other hair cosmetic tasks.
  • Another object of the invention is therefore an aqueous hair care product for reducing the greasy appearance of the hair, which 1-20% by weight of a zwitterionic polymer, which essentially consists of
  • Suitable anionic surfactants in preparations according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group,
  • Ether carboxylic acids of the formula RO- (CH 2 -CH O) x -CH 2 -COOH, in which R is a linear alkyl group with 10 to 22 C atoms and x 0 or 1 to 16, acyl sarcosides with 10 to 18 C atoms in the acyl group, acyl taurides with 10 to 18 C atoms in the acyl group, acyl isethionates with 10 to 18 C atoms in the acyl group,
  • Alpha-sulfofatty acid methyl esters of fatty acids with 12 to 18 carbon atoms, alkyl sulfates and alkyl polyglycol ether sulfates of the formula R- (OCH -CH) -OSO H, in which R is a preferably linear alkyl group with 10 to 18 carbon atoms and x 0 or 1 to 12 is
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one in the molecule
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyl dimethylammonium glycinate, and 2-alkyl -3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine.
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C 8 -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO H group in the molecule and are used for Are capable of forming internal salts.
  • suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N- alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-
  • Alkyltaurines N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are the N-cocoalkylaminopropionate and the cocoacylaminoethylaminopropionate.
  • Nonionic surfactants contain z as a hydrophilic group.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such connections are, for example
  • Examples of the cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • Ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearyltrimethyla monium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride.
  • the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM -2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80).
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are notable for their good biodegradability.
  • estersquats such as the Diacyloxyethyl- marketed under the trademark Stepantex ® are dimethyl-methosulfates and methyl hydroxyalkyldialkoyloxyalkyl- methosulfates.
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to CTFA nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride”.
  • the compounds with alkyl or acyl groups used as surfactants can each be uniform substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with different chain lengths depending on the respective raw material are obtained.
  • Another object of the invention is an aqueous hair care product in the form of a
  • a cationic surfactant 1-5% by weight of a cationic surfactant and, if appropriate
  • the cationic surfactants counteract the static chargeability of the hair in such preparations, which makes combing easier and the fit of the hairstyle improved.
  • the cationic polymers are characterized by a lasting improvement in the combability of wet hair and the detangling ability of dry hair. In this way, hair that has been damaged or damaged in the structure by numerous dyeing or permanent wave processes is noticeably softened.
  • the hair rinses according to the invention are therefore also suitable as hair treatment preparations for greasy hair or hair prone to re-greasing, in particular after dyeing and permanent wave applications.
  • Suitable cationic polymers are synthetic polymers or natural polysaccharide or protein derivatives that contain a cationic grouping z. B. contain a tertiary amino group or a quaternary ammonium group in the chain or on the chain. Examples of such suitable cationic polymers are e.g. B.
  • Quaternized cellulose derivatives such as z. B. are sold under the trade name Celquat ® L200 or Polymer JR 400, polysiloxanes with quaternary ammonium groups,
  • Dimethyl-diallylammonium chloride polymers and their copolymers with acrylamide, such as z. B. are commercially available under the trademark Merquat ® 550, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers, quaternized with dimethyl sulfate, such as those used for. B. are commercially available under the trademark Gafquat ® 755, vinylimidazolinium methoxychloride-vinylpyrrolidone copolymers (Luviquat FC550)
  • Another object of the invention is an aqueous hair care product in the form of a
  • Preferred anionic surfactants are alkyl polyglycol ether sulfates with 10-16 C atoms in the alkyl group and 1-12 glycol ether groups in the form of their alkali metal, magnesium or ammonium salts or also alkyl sulfates with 10-16 C atoms in the alkyl group in the form of their mono-, di - Or contain triethanolammonium salts or their isopropanolammonium salts.
  • auxiliaries and additives that can be contained in the inventive hair conditioners and shampoos are, for. B.
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed glow, dextrans, cellulose derivatives, e.g. As methyl cellulose, hydroxyalkyl cellulose and carboxy methyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B. bentonite or fully synthetic hydrocolloids such.
  • Structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin,
  • Protein hydrolyzates especially elastin, collagen, keratin, milk protein,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol
  • Anti-dandruff agents such as Piroctone Olamine and Zink Omadine, salicylic acid other substances for adjusting the pH value
  • Active ingredients such as panthenol, pantothenic acid, niacinamide, allantoin,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as whale, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters,
  • Swelling and penetration substances such as glycerin, propylene glycol monoethyl ether,
  • Pearlescent agents such as ethylene glycol mono- and distearate
  • Blowing agents such as propane-butane mixtures, NO, dimethyl ether, CO and air,
  • Preservatives such as B. p-hydroxybenzoic acid ester, phenoxyethanol and
  • Dehyquart A Cetyltrimethylammonium chloride 25% by weight in water (Henkel KGaA)
  • Celquat ® L 200 cellulose derivative, quaternized (Polyquaternium-4) (National Starch & Chemical)
  • Euxyl ® K 400 methyldibromoglutaronitrile (20% by weight) in phenoxyethanol. (Schülke & Mayr)
  • Cremophor ® RH 40 hydraulic castor oil oxethylate (40 mol EO).
  • BASF Natrosol ® 250 HR: hydroxyethyl cellulose (Hercules)
  • Luviskol ® K 30 Polyvinylpyrrolidone (K-value 27-33).
  • BASF Texapon ® N50: alkyl (C ⁇ 2/14 ) polyglycol ether (2EO) sulfate, Na salt, 28% by weight in water (Henkel KGaA)
  • Dehyton ® G N- (2-hydroxyethyl) -N-kokosalkylamidoethylcarboxymethyl- glycinate. Na salt.
  • Polymer JR ® 400 hydroxyethyl cellulose quaternized (Polyquaternium -10).
  • the pre-cleaned hair strands were measured for their volume using the silhouette method.
  • Sebum comb 'combed 100 times and measured again.
  • he sebum comb contains a reservoir made of cellulose filling material and fiber tines
  • Fiber post material It is used for the defined application of sebum (synthetic skin fat according to Bey), which is contained in the reservoir as a 5% solution in isopropanol and at
  • Combing is applied to the strand of hair.
  • the experiment shows that the zwitterionic polymer S in hair conditioner (1) improves the fullness of the hair. He also shows that a defined supply of sebum leads to a smaller decrease in the fullness of the hair than in the case of hair treated with formulation IV (without zwitterionic polymer).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
  • Dermatology (AREA)
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Abstract

L'invention concerne des produits de soins capillaires servant à réduire l'aspect gras des cheveux et contenant comme constituants des polymères à ions dipolaires comprenant des groupes carboxyle libres et des groupes ammonium quaternaires. Les produits de soins capillaires aqueux ainsi que ceux qui, après application sur les cheveux, doivent être rincés, et les polymères à ions dipolaires comprenant des groupes carboxyle libres et des groupes ammonium quaternaires contiennent un tensioactif dans des quantités comprises entre 1 à 10 % en poids et 1 à 30 % en poids ; ils améliorent le volume des cheveux et diminuent l'aspect gras ou en mèches de la coiffure.
PCT/EP2000/010998 1999-11-17 2000-11-08 Produits de soins capillaires antigras WO2001035909A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1999155239 DE19955239A1 (de) 1999-11-17 1999-11-17 Antifett-Haarpflegemittel
DE19955239.8 1999-11-17

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WO2001035909A1 true WO2001035909A1 (fr) 2001-05-25

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11512266B2 (en) 2019-07-16 2022-11-29 The Procter & Gamble Company Disinfectant composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3629241A1 (de) * 1985-08-30 1987-03-05 Oreal Uv-strahlung-filtrierende polyaminoamide, verfahren zu deren herstellung und verwendung derselben als haut- und haarschutz
DE3716380A1 (de) * 1986-05-16 1987-11-19 Oreal Mittel und verwendung von partiell acetyliertem polyvinylalkohol als schaeumungsagens, wobei die mittel als aerosol vorliegen
US4842851A (en) * 1986-06-02 1989-06-27 L'oreal Polyamino amides for protecting hair against atmospheric attack, and in particular against light, and process for protecting hair employing such polyaminoamides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3629241A1 (de) * 1985-08-30 1987-03-05 Oreal Uv-strahlung-filtrierende polyaminoamide, verfahren zu deren herstellung und verwendung derselben als haut- und haarschutz
DE3716380A1 (de) * 1986-05-16 1987-11-19 Oreal Mittel und verwendung von partiell acetyliertem polyvinylalkohol als schaeumungsagens, wobei die mittel als aerosol vorliegen
US4842851A (en) * 1986-06-02 1989-06-27 L'oreal Polyamino amides for protecting hair against atmospheric attack, and in particular against light, and process for protecting hair employing such polyaminoamides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11512266B2 (en) 2019-07-16 2022-11-29 The Procter & Gamble Company Disinfectant composition

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