WO1999011226A1 - Compositions pour le conditionnement des cheveux - Google Patents

Compositions pour le conditionnement des cheveux Download PDF

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Publication number
WO1999011226A1
WO1999011226A1 PCT/US1997/014161 US9714161W WO9911226A1 WO 1999011226 A1 WO1999011226 A1 WO 1999011226A1 US 9714161 W US9714161 W US 9714161W WO 9911226 A1 WO9911226 A1 WO 9911226A1
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WO
WIPO (PCT)
Prior art keywords
acid
melting point
hair conditioning
fatty
mixtures
Prior art date
Application number
PCT/US1997/014161
Other languages
English (en)
Inventor
Haruo Tamura
Kiichiro Nakamura
Original Assignee
The Procter & Gamble Company
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 The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP10541591A priority Critical patent/JP2000507976A/ja
Priority to BR9714855-5A priority patent/BR9714855A/pt
Priority to EP97940551A priority patent/EP1011611A1/fr
Priority to PCT/US1997/014161 priority patent/WO1999011226A1/fr
Priority to AU42302/97A priority patent/AU4230297A/en
Publication of WO1999011226A1 publication Critical patent/WO1999011226A1/fr

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    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides

Definitions

  • the present invention relates to hair conditioning compositions containing amidoamine and selected acids which provide good conditioning benefits.
  • Scalp and hair become soiled due to their contact with the surrounding environment and from sebum secreted from the hair follicles.
  • the build-up of sebum and environmental soiling can cause the hair to have a dirty or greasy feel, and an unattractive appearance.
  • the present invention is directed to a hair conditioning composition
  • a hair conditioning composition comprising by weight: (a) from about 0.6% to about 9.0% of an amidoamine; (b) from about 0.1 % to about 10.0% of an acid selected from the group consisting of acetic acid, tartaric acid, fumaric acid, lactic acid, malic acid, succinic acid, and mixtures thereof; (c) from about 1 % to about 15% of a high melting point compound having a melting point of at least about 25°C selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, hydrocarbons, steroids, and mixtures thereof; and (d) water; wherein the pH of the hair conditioning composition is from about 2.5 to about 4.5, and wherein the composition is substantially free of quaternary ammonium compounds.
  • the present invention is further directed to a suitable process for providing the hair conditioning composition.
  • compositions of the present invention comprise by weight from about 0.6% to about 9.0%, preferably from about 1.0% to about 6.0% of an amidoamine having the following general formula:
  • Preferred amidoamines useful herein include stearamidopropyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethylamine, palmitamidopropyldiethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethylamine, behenamidopropyldiethylamine, behenamidoethyldiethylamine, behenamidoethyldimethylamine, arachidamidopropyldimethylamine, arachidamidopropyldiethylamine, arachidamidoethyldiethylamine, arachidamidoethyldiethylamine, arachidamidoethyldimethylamine,
  • amidoamines useful herein include: stearamidopropyldimethylamine with tradenames LEXAMINE S-13 available from Inolex (Philadelphia Pennsylvania, USA) and AMIDOAMINE MSP available from Nikko (Tokyo, Japan), stearamidoethyldiethylamine with a tradename AMIDOAMINE S available from Nikko, behenamidopropyldimethylamine with a tradename INCROMINE BB available from Croda (North Humberside, England), and various amidoamines with tradenames SCHERCODINE series available from Scher (Clifton New Jersey, USA).
  • ACIDINE stearamidopropyldimethylamine with tradenames LEXAMINE S-13 available from Inolex (Philadelphia Pennsylvania, USA) and AMIDOAMINE MSP available from Nikko (Tokyo, Japan)
  • stearamidoethyldiethylamine with a tradename AMIDOAMINE S available from Nikk
  • compositions of the present invention comprise by weight from about 0.1 % to about 10.0%, preferably from about 0.2% to about 5.0%, of a selected group of acids.
  • the acid is also included at such a level to provide the hair conditioning composition with a pH of between from about 2.5 to about 4.5.
  • the gel made with the selected acids, the amidoamine mentioned above and the high melting point compounds mentioned below provides the composition to have a suitable viscosity.
  • a suitable viscosity herein would provide the conditioning composition to be thick enough to give a favorable creamy texture, yet flowable enought that it is easily dispsensed.
  • the acid useful herein is selected from the group consisting of acetic acid, tartaric acid, fumaric acid, lactic acid, malic acid, succinic acid, and mixtures thereof.
  • the acid is selected from the group consisting of acetic acid, tartaric acid, fumaric acid, and mixtures thereof.
  • acids useful herein are those having the same tradenames as their compound names including: lactic acid with a tradename UNICHEM LACA available from UPI and same tradename as the compound name from Showa Kako, malic acid with the same tradename as the compound name available from Kyowa Hakko (Tokyo, Japan) and Fuso Kagaku (Osaka, Japan), acetic acid with the same tradename as the compound name available from Denki Kagaku Kogyo, and tartaric acid, fumaric acid, and succinic acid with the same tradenames as the compound names available from Fuso Kagaku. HIGH MELTING POINT COMPOUND
  • compositions of the present invention comprise by weight from about 1 % to about 15%, preferably from about 1.4% to about 10%, more preferably from about 3% to about 8% of a high melting point compound having a melting point of at least about 25°C selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, hydrocarbons, steroids, and mixtures thereof.
  • a high melting point compound having a melting point of at least about 25°C selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, hydrocarbons, steroids, and mixtures thereof.
  • these high melting point compounds cover the hair surface and reduce friction, thereby resulting in providing smooth feel on the hair and ease of combing. It is understood by the artisan that the compounds disclosed in this section of the specification can in some instances fall into more than one classification, e.g., some fatty alcohol derivatives can also be classified as fatty acid derivatives.
  • a given classification is not intended to be a limitation on that particular compound, but is done so for convenience of classification and nomenclature. Further, it is understood by the artisan that, depending on the number and position of double bonds, and length and position of the branches, certain compounds having certain required carbon atoms may have a melting point of less than about 25°C. Such compounds of low melting point are not intended to be included in this section. Nonlimiting examples of the high melting point compounds are found in International Cosmetic Ingredient Dictionary, Fifth Edition, 1993, and CTFA Cosmetic Ingredient Handbook, Second Edition, 1992, both of which are incorporated by reference herein in their entirety.
  • the fatty alcohols useful herein are those having from about 14 to about 30 carbon atoms, preferably from about 16 to about 22 carbon atoms. These fatty alcohols can be straight or branched chain alcohols and can be saturated or unsaturated. Nonlimiting examples of fatty alcohols include, cetyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof.
  • the fatty acids useful herein are those having from about 10 to about 30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more preferably from about 16 to about 22 carbon atoms. These fatty acids can be straight or branched chain acids and can be saturated or unsaturated. Also included are diacids, triacids, and other multiple acids which meet the requirements herein. Also included herein are salts of these fatty acids. Nonlimiting examples of fatty acids include lauric acid, palmitic acid, stearic acid, behenic acid, sebacic acid, and mixtures thereof.
  • the fatty alcohol derivatives and fatty acid derivatives useful herein include alkyl ethers of fatty alcohols, alkoxyiated fatty alcohols, alkyl ethers of alkoxyiated fatty alcohols, esters of fatty alcohols, fatty acid esters of compounds having esterifiable hydroxy groups, hydroxy-substitued fatty acids, and mixtures thereof.
  • Nonlimiting examples of fatty alcohol derivatives and fatty acid derivatives include materials such as methyl stearyl ether; the ceteth series of compounds such as ceteth-1 through ceteth-45, which are ethylene glycol ethers of cetyl alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; the steareth series of compounds such as steareth-1 through 10, which are ethylene glycol ethers of steareth alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; ceteareth 1 through ceteareth-10, which are the ethylene glycol ethers of ceteareth alcohol, i.e.
  • Hydrocarbons useful herein include compounds having at least about 20 carbons.
  • Steroids useful herein include compounds such as cholesterol.
  • High melting point compounds of a single compound of high purity are preferred.
  • Single compounds of pure fatty alcohols selected from the group of pure cetyl alcohol, stearyl alcohol, and behenyl alcohol are highly preferred.
  • pure herein, what is meant is that the compound has a purity of at least about 90%, preferably at least about 95%.
  • high melting point compounds useful herein include: cetyl alchol, stearyl alcohol, and behenyl alcohol having tradenames KONOL series available from New Japan Chemical (Osaka, Japan), and NAA series available from NOF (Tokyo, Japan); pure behenyl alcohol having tradename 1-DOCOSANOL available from WAKO (Osaka, Japan), various fatty acids having tradenames NEO-FAT available from Akzo (Chicago Illinois, USA), HYSTRENE available from Witco Corp. (Dublin Ohio, USA), and DERMA available from Vevy (Genova, Italy); and cholesterol having tradename NIKKOL AGUASOME LA available from Nikko.
  • compositions of the present invention comprise water for the remainder of the components described above, and other additional components as described hereinafter.
  • Deionized water is preferably used.
  • Water from natural sources including mineral cations can also be used, depending on the desired characteristic of the product. FREE OF QUATERNARY AMMONIUM COMPOUNDS
  • compositions of the present invention are substantially free of quaternary ammonium compounds, which are commonly used in the art.
  • quaternary ammonium compounds are those of the general formula:
  • R 1 , R 2 , R3 and R 4 is selected from an aliphatic group of from 8 to 30 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having up to about 22 carbon atoms, the remainder of R ⁇ , R 2 , R3 and R 4 are independently an aliphatic group of from about 1 to about 22 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having from about 1 to about 22 carbon atoms; and X is a salt-forming anion such as those selected from halogen, (e.g.
  • the aliphatic groups may contain, in addition to carbon and hydrogen atoms, ether linkages, and other groups such as amino groups.
  • compositions of the present invention may further comprise by weight from about 0.02% to about 2%, preferably from about 0.2% to about 1.5% of an oily compound having a melting point of not more than about 25° C selected from the group consisting of a first oily compound, a second oily compound, and mixtures thereof.
  • the oily compounds useful herein may be volatile or nonvolatile. Without being bound by theory, it is believed that, the oily compounds may penetrate the hair to modify the hydroxy bonds of the hair, thereby resulting in providing softness and flexibility to the hair.
  • the oily compound may comprise either the first oily compound or the second oily compound as described herein. Preferably, a mixture of the first oily compound and the second oily compound is used.
  • oily compounds of this section are to be distinguished from the high melting point compounds described above.
  • Nonlimiting examples of the oily compounds are found in International Cosmetic Ingredient Dictionary, Fifth Edition, 1993, and CTFA Cosmetic Ingredient Handbook, Second Edition, 1992, both of which are incorporated by reference herein in their entirety.
  • the first oily compound may be included in the compositions of the present invention.
  • the compositions of the present invention comprise by weight from about 0.1 % to 0.75% of a first oily compound.
  • the first oily compounds useful herein are selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, and mixtures thereof.
  • the fatty alcohols useful herein include those having from about 10 to about 30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more preferably from about 16 to about 22 carbon atoms. These fatty alcohols can be straight or branched chain alcohols and can be saturated or unsaturated alcohols, preferably unsaturated alcohols. Nonlimiting examples of these compounds include oleyl alcohol, palmitoleic alcohol, isostearyl alcohol, isocetyl alchol, undecanol, octyl dodecanol, octyl decanol, octyl alcohol, caprylic alcohol, decyl alcohol and lauryl alcohol.
  • the fatty acids useful herein include those having from about 10 to about 30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more preferably from about 16 to about 22 carbon atoms. These fatty acids can be straight or branched chain acids and can be saturated or unsaturated. Suitable fatty acids include, for example, oleic acid, linoleic acid, isostearic acid, linolenic acid, ethyl linolenic acid, ethyl linolenic acid, arachidonic acid, and ricinolic acid.
  • the fatty acid derivatives and fatty alcohol derivatives are defined herein to include, for example, esters of fatty alcohols, alkoxyiated fatty alcohols, alkyl ethers of fatty alcohols, alkyl ethers of alkoxyiated fatty alcohols, and mixtures thereof.
  • first oily compounds useful herein include: oleyl alcohol with tradename UNJECOL 90BHR available from New Japan Chemical, pentaerythritol tetraisostearate and trimethylolpropane t isostearate with tradenames KAKPTI and KAKTTI available from Kokyu Alcohol (Chiba, Japan), pentaerythritol tetraoleate having the same tradename as the compound name available from New Japan Chemical, trimethylolpropane trioleate with a tradename ENUJERUBU TP3SO available from New Japan Chemical, various liquid esters with tradenames SCHERCEMOL series available from Scher, and hexyl isostearate with a tradename HIS and isopropryl isostearate having a tradename ZPIS available from Kokyu Alcohol.
  • the second oily compound may be included in the compositions of the present invention.
  • the compositions of the present invention comprise by weight from about 0.1% to about 0.75% of a second oily compound.
  • the second oily compounds useful herein include straight chain, cyclic, and branched chain hydrocarbons which can be either saturated or unsaturated, so long as they have a melting point of not more than about 25°C. These hydrocarbons have from about 12 to about 40 carbon atoms, preferably from about 12 to about 30 carbon atoms, and preferably from about 12 to about 22 carbon atoms.
  • polymeric hydrocarbons of alkenyl monomers such as polymers of C2-6 alkenyl monomers. These polymers can be straight or branched chain polymers.
  • the straight chain polymers will typically be relatively short in length, having a total number of carbon atoms as described above.
  • the branched chain polymers can have substantially higher chain lengths.
  • the number average molecular weight of such materials can vary widely, but will typically be up to about 500, preferably from about 200 to about 400, and more preferably from about 300 to about 350.
  • mineral oils are liquid mixtures of hydrocarbons that are obtained from petroleum.
  • hydrocarbon materials include paraffin oil, mineral oil, dodecane, isododecane, hexadecane, isohexadecane, eicosene, isoeicosene, tridecane, tetradecane, polybutene, polyisobutene, and mixtures thereof.
  • hydrocarbons selected from the group consisting of mineral oil, isododecane, isohexadecane, polybutene, polyisobutene, and mixtures thereof.
  • second oily compounds useful herein include isododecane, isohexadeance, and isoeicosene with tradenames PERMETHYL 99A, PERMETHYL 101 A, and PERMETHYL 1082, available from Presperse (South Plainfield New Jersey, USA), a copolymer of isobutene and normal butene with tradenames INDOPOL H-100 available from Amoco Chemicals (Chicago Illinois, USA), mineral oil with tradename BENOL available from Witco, and isoparaffin with tradename ISOPAR from Exxon Chemical Co. (Houston Texas, USA).
  • Cationic polymers useful herein are those which are more or less water soluble.
  • the term “polymer” shall include materials whether made by polymerization of one type of monomer or made by two (i.e., copolymers) or more types of monomers.
  • water soluble cationic polymer, what is meant is a polymer which is sufficiently soluble in water to form a substantially clear solution to the naked eye at a concentration of 0.1% in water (distilled or equivalent) at 25°C. The preferred polymer will be sufficiently soluble to form a substantially clear solution at 0.5% concentration, more preferably at 1.0% concentration.
  • the cationic polymers hereof will generally have a weight average molecular weight which is at least about 5,000, typically at least about 10,000, and is less than about 10 million. Preferably, the molecular weight is from about 100,000 to about 2 million.
  • the cationic polymers will generally have cationic nitrogen-containing moieties such as quaternary ammonium or cationic amino moieties, and mixtures thereof.
  • the cationic charge density is preferably at least about 0.1 meq/gram, more preferably at least about 1.5 meq/gram, even more preferably at least about 1.1 meq/gram, still more preferably at least about 1.2 meq/gram.
  • Cationic charge density of the cationic polymer can be determined according to the Kjeldahl Method. Those skilled in the art will recognize that the charge density of amino-containing polymers may vary depending upon pH and the isoelectric point of the amino groups. The charge density should be within the above limits at the pH of intended use.
  • Any anionic counterions can be utilized for the cationic polymers so long as the water solubility criteria is met.
  • Suitable counterions include halides (e.g., Cl, Br, I, or F, preferably Cl, Br, or I), sulfate, and methylsulfate. Others can also be used, as this list is not exclusive.
  • the cationic nitrogen-containing moiety will be present generally as a substituent, on a fraction of the total monomer units of the cationic hair conditioning polymers.
  • the cationic polymer can comprise copolymers, terpolymers, etc. of quaternary ammonium or cationic amine- substituted monomer units and other non-cationic units referred to herein as spacer monomer units.
  • Such polymers are known in the art, and a variety can be found in the CTFA Cosmetic Ingredient Dictionary, 3rd edition, edited by Estrin, Crosley, and Haynes, (The Cosmetic, Toiletry, and Fragrance Association, Inc., Washington, D.C., 1982).
  • Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as acrylamide, methacrylamide, alkyl and dialkyl acrylamides, alkyl and dialkyl methacrylamides, alkyl acrylate, alkyl methacrylate, vinyl caprolactone, and vinyl pyrrolidone.
  • the alkyl and dialkyl substituted monomers preferably have C-
  • Other suitable spacer monomers include vinyl esters, vinyl alcohol (made by hydrolysis of polyvinyl acetate), maleic anhydride, propylene glycol, and ethylene glycol.
  • the cationic amines can be primary, secondary, or tertiary amines, depending upon the particular species and the pH of the composition. In general, secondary and tertiary amines, especially tertiary amines, are preferred.
  • Amine-substituted vinyl monomers can be polymerized in the amine form, and then optionally can be converted to ammonium by a quaternization reaction.
  • Amines can also be similarly quaternized subsequent to formation of the polymer.
  • tertiary amine functionalities can be quaternized by reaction with a salt of the formula R'X wherein R' is a short chain alkyl, preferably a C-
  • Suitable cationic amino and quaternary ammonium monomers include, for example, vinyl compounds substituted with dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, monoalkylaminoalkyi acrylate, monoalkylaminoalkyi methacrylate, trialkyi methacryloxyalkyi ammonium salt, trialkyi acryloxyalkyi ammonium salt, diallyl quaternary ammonium salts, and vinyl quaternary ammonium monomers having cyclic cationic nitrogen-containing rings such as pyridinium, imidazolium, and quaternized pyrrolidone, e.g., alkyl vinyl imidazolium, alkyl vinyl pyridinium, alkyl vinyl pyrrolidone salts.
  • the alkyl portions of these monomers are preferably lower alkyls such as the C-
  • Suitable amine-substituted vinyl monomers for use herein include dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, dialkylaminoalkyl acrylamide, and dialkylaminoalkyl methacrylamide, wherein the alkyl groups are preferably C-
  • the cationic polymers hereof can comprise mixtures of monomer units derived from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers.
  • Suitable cationic hair conditioning polymers include, for example: copolymers of 1-vinyl-2-pyrrolidone and 1-vinyl-3-methylimidazolium salt (e.g., chloride salt) (referred to in the industry by the Cosmetic, Toiletry, and Fragrance Association, "CTFA", as Polyquaternium-16), such as those commercially available from BASF Wyandotte Corp.
  • CTFA Cosmetic, Toiletry, and Fragrance Association
  • cationic polymers that can be used include polysaccharide polymers, such as cationic cellulose derivatives and cationic starch derivatives.
  • Cationic polysaccharide polymer materials suitable for use herein include those of the formula:
  • A is an anhydroglucose residual group, such as a starch or cellulose anhydroglucose residual
  • R is an alkylene oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or combination thereof
  • R 1 , R 2 , and R 3 independently are alkyl, aryl, alkylaryl, arylalkyi, alkoxyalkyl, or alkoxyaryl groups, each group containing up to about 18 carbon atoms, and the total number of carbon atoms for each cationic moiety (i.e., the sum of carbon atoms in Rl , R 2 and R 3 ) preferably being about 20 or less
  • X is an anionic counterion, as previously described.
  • Cationic cellulose is available from Amerchol Corp. (Edison, NJ, USA) in their Polymer JR® and LR® series of polymers, as salts of hydroxyethyl cellulose reacted with trimethyl ammonium substituted epoxide, referred to in the industry (CTFA) as Polyquatemium 10.
  • CTFA trimethyl ammonium substituted epoxide
  • Another type of cationic cellulose includes the polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide, referred to in the industry (CTFA) as Polyquatemium 24. These materials are available from Amerchol Corp. (Edison, NJ, USA) under the tradename Polymer LM-200®.
  • cationic polymers that can be used include cationic guar gum derivatives, such as guar hydroxypropyltrimonium chloride (commercially available from Celanese Corp. in their Jaguar R series).
  • Other materials include quaternary nitrogen-containing cellulose ethers (e.g., as described in U.S. Patent 3,962,418, incorporated herein by reference), and copolymers of etherified cellulose and starch (e.g., as described in U.S. Patent 3,958,581, incorporated herein by reference.) Silicones
  • Silicones useful herein are volatile soluble or insoluble, or nonvolatile soluble or insoluble.
  • soluble what is meant is that the silicones are miscible with water so as to form part of the same phase.
  • insoluble what is meant is that the silicones forms a separate, discontinuous phase from the carrier, such as in the form of an emulsion or a suspension of droplets of the silicones.
  • the nonvolatile dispersed silicones compounds useful herein will preferably have a viscosity of from about 1 ,000 to about 2,000,000 centistokes at 25°C, more preferably from about 10,000 to about 1,800,000, and even more preferably from about 100,000 to about 1,500,000.
  • the viscosity can be measured by means of a glass capillary viscometer as set forth in Dow Corning Corporate Test Method CTM0004, July 20, 1970, which is incorporated by reference herein in its entirety.
  • Suitable silicone fluids include polyalkyl siloxanes, polyaryl siloxanes, polyalkylaryl siloxanes, polyether siloxane copolymers, and mixtures thereof. Other nonvolatile silicones having hair conditioning properties can also be used.
  • nonvolatile dispersed silicones herein also include polyalkyl or polyaryl siloxanes with the following structure (I)
  • R is alkyl or aryl
  • x is an integer from about 7 to about 8,000.
  • A represents groups which block the ends of the silicone chains.
  • the alkyl or aryl groups substituted on the siloxane chain (R) or at the ends of the siloxane chains (A) can have any structure as long as the resulting silicone remains fluid at room temperature, is dispersible, is neither irritating, toxic nor otherwise harmful when applied to the hair, is compatible with the other components of the composition, is chemically stable under normal use and storage conditions, and is capable of being deposited on and conditions the hair.
  • Suitable A groups include hydroxy, methyl, methoxy, ethoxy, propoxy, and aryloxy.
  • the two R groups on the silicon atom may represent the same group or different groups.
  • the two R groups represent the same group.
  • Suitable R groups include methyl, ethyl, propyl, phenyl, methylphenyl and phenylmethyl.
  • the preferred silicones are polydimethylsiloxane, polydiethylsiloxane, and polymethylphenylsiloxane. Polydimethylsiloxane, which is also known as dimethicone, is especially preferred.
  • the polyalkylsiloxanes that can be used include, for example, polydimethylsiloxanes. These silicones are available, for example, from the General Electric Company in their ViscasilR and SF 96 series, and from Dow Corning in their Dow Corning 200 series.
  • Polyalkylaryl siloxanes can also be used and include, for example, polymethylphenylsiloxanes. These siloxanes are available, for example, from the General Electric Company as SF 1075 METHYL PHENYL FLUID or from Dow Corning as 556 COSMETIC GRADE FLUID.
  • highly arylated silicones such as highly phenylated polyethyl silicone having refractive index of about 1.46 or higher, especially about 1.52 or higher.
  • a spreading agent such as a surfactant or a silicone resin, as described below to decrease the surface tension and enhance the film forming ability of the material.
  • nonvolatile dispersed silicones include amino substituted materials.
  • Suitable alkylamino substituted silicones include those represented by the following structure (II)
  • G is chosen from the group consisting of hydrogen, phenyl, OH, C-
  • n and m are selected depending on the exact molecular weight of the compound desired.
  • R3 denotes a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, preferably an alkyl or alkenyl radical such as methyl
  • R 4 denotes a hydrocarbon radical, preferably a Ci - C-
  • Q is a halide, preferably chloride
  • r denotes an average statistical value from 2 to 20, preferably from 2 to 8
  • s denotes an average statistical value from 20 to 200, and preferably from 20 to 50.
  • a preferred polymer of this class is available from Union Carbide under the name "UCAR SILICONE ALE 56.”
  • references disclosing suitable nonvolatile dispersed silicones include U.S. Patent No. 2,826,551 , to Geen; U.S. Patent No. 3,964,500, to Drakoff, issued June 22, 1976; U.S. Patent No. 4,364,837, to Pader; and British Patent No. 849,433, to Woolston, all of which are incorporated herein by reference in their entirety. Also incorporated herein by reference in its entirety is "Silicon Compounds" distributed by Petrarch Systems, Inc., 1984. This reference provides an extensive, though not exclusive, listing of suitable silicones.
  • silicone gum means a polyorganosiloxane material having a viscosity at 25°C of greater than or equal to 1,000,000 centistokes. It is recognized that the silicone gums described herein can also have some overlap with the above-disclosed silicones. This overlap is not intended as a limitation on any of these materials. Silicone gums are described by Petrarch, and others including U.S. Patent No. 4,152,416, to Spitzer et al., issued May 1 , 1979 and Noll, Walter, Chemistry and Technology of Silicones, New York: Academic Press 1968.
  • silicone gums will typically have a mass molecular weight in excess of about 200,000, generally between about 200,000 and about 1,000,000. Specific examples include polydimethylsiloxane, polydimethylsiloxane methylvinylsiloxane) copolymer, polydimethylsiloxane diphenylsiloxane methylvinylsiloxane) copolymer and mixtures thereof.
  • silicone resins which are highly crosslinked polymeric siloxane systems.
  • the crosslinking is introduced through the incorporation of tri-functional and tetra-functional silanes with mono- functional or di-functional, or both, silanes during manufacture of the silicone resin.
  • the degree of crosslinking that is required in order to result in a silicone resin will vary according to the specific silane units incorporated into the silicone resin.
  • silicone materials which have a sufficient level of trifunctional and tetrafunctional siloxane monomer units, and hence, a sufficient level of crosslinking, such that they dry down to a rigid, or hard, film are considered to be silicone resins.
  • the ratio of oxygen atoms to silicon atoms is indicative of the level of crosslinking in a particular silicone material.
  • Silicone materials which have at least about 1.1 oxygen atoms per silicon atom will generally be silicone resins herein.
  • the ratio of oxygen:silicon atoms is at least about 1.2:1.0.
  • Silanes used in the manufacture of silicone resins include monomethyl, dimethyl, trimethyl, monophenyl, diphenyl, methylphenyl, monovinyl, and methylvinylchlorosilanes, and tetrachlorosilane, with the methyl substituted silanes being most commonly utilized.
  • Preferred resins are offered by General Electric as GE SS4230 and SS4267.
  • silicone resins will generally be supplied in a dissolved form in a low viscosity volatile or nonvolatile silicone fluid.
  • the silicone resins for use herein should be supplied and incorporated into the present compositions in such dissolved form, as will be readily apparent to those skilled in the art. Without being bound by theory, it is believed that the silicone resins can enhance deposition of other silicones on the hair and can enhance the glossiness of hair with high refractive index volumes.
  • silicone resin powders such as the material given the CTFA designation polymethylsilsequioxane, which is commercially available as TospearlTM f rom Toshiba Silicones.
  • Silicone materials and silicone resins in particular, can conveniently be identified according to a shorthand nomenclature system well known to those skilled in the art as the "MDTQ" nomenclature. Under this system, the silicone is described according to the presence of various siloxane monomer units which make up the silicone. Briefly, the symbol M denotes the mono-functional unit (CH3)3SiO) 5; D denotes the difunctional unit (CH3) 2 SiO; T denotes the trifunctional unit (CH3)SiO ⁇ 5; and Q denotes the quadri- or tetra-functional unit SiO 2 .
  • Primes of the unit symbols denote substituents other than methyl, and must be specifically defined for each occurrence. Typical alternate substituents include groups such as vinyl, phenyl, amino, hydroxyl, etc.
  • the molar ratios of the various units either in terms of subscripts to the symbols indicating the total number of each type of unit in the silicone, or an average thereof, or as specifically indicated ratios in combination with molecular weight, complete the description of the silicone material under the MDTQ system. Higher relative molar amounts of T, Q, T and/or Q' to D, D', M and/or or M' in a silicone resin is indicative of higher levels of crosslinking. As discussed before, however, the overall level of crosslinking can also be indicated by the oxygen to silicon ratio.
  • the silicone resins for use herein which are preferred are MQ, MT, MTQ, MQ and MDTQ resins.
  • the preferred silicone substituent is methyl.
  • MQ resins wherein the M:Q ratio is from about 0.5:1.0 to about 1.5:1.0 and the average molecular weight of the resin is from about 1000 to about 10,000.
  • proteins useful herein include: materials having tradenames CROTEIN series available from Croda, and PROMOIS series available from Seiwa Kasei. ADDITIONAL COMPONENTS
  • Additional components can be formulated into the present composition. These additional components are selected by the artisan according to the desired characteristics of the final product. Additional components include nonionic surfactants, amphoteric surfactants, zwitterionic surfactants; aqueous solvents such as C-
  • the hair conditioning compositions of the present invention are preferably made by a method comprising three steps.
  • the first step comprises mixing water, the amidoamine, and a portion of the acid at a temperature of at least 70°C.
  • the second step comprises addition of the high melting point compound to the obtained mixture while maintaining the temperature. Agitation usually accompanies the second step.
  • the third step comprises cooling the obtained mixture to a temperature below 60°C, wherein the remaining acid, if any, is added. Then, the other components are added.
  • compositions of various characteristics can be made.
  • a conditioning composition which provides relatively more shear-thinning property is obtained. This rheology can be recognized by the consumer as good spreadability and good rinsability.
  • a conditioning composition which provides relatively less shear-thinning property is obtained. This rheology can be recognized by the consumer as richness, and creaminess.
  • the amount of acid to include in the first step is determined in view of the components used in the composition according to the desired benefits of the final product.
  • the low melting point oily compound if included, can be added either in the first step or after the third step. By changing at which step the low melting point oily compound is added, the optimum conditioning level expected from the low melting point oily compound can be adjusted.
  • water, stearamidopropyldimethylamine, about 50% of acid, and low melting point oily compound, if included, are mixed at a temperature above 70°C. Then the high melting point fatty compounds, EDTA and benzyl alcohol are added with agitation. After cooling down below 60°C, the remaining acid and other remaining components are added with agitation, then cooled down to about 30°C.
  • Examples I through IV have many advantages. For example, they can provide richness and creaminess to the wet hair, and also show good combing feel and lustery appearance when the hair is dry.
  • EXAMPLES V - VIII have many advantages. For example, they can provide richness and creaminess to the wet hair, and also show good combing feel and lustery appearance when the hair is dry.
  • Examples V through VIII are hair rinse compositions having the same compositions as disclosed above for Examples I through IV, respectively, made with the following method.
  • Examples V through VIII have many advantages. For example, they can provide good spreadability and good rinsability when the wet hair, and also show good combing feel and lustery appearance when the hair is dry.
  • Examples IX through XII have many advantages. For example, they can provide richness and creaminess to the wet hair, and also show good combing feel and lustery appearance when the hair is dry. EXAMPLES XIII - XVI
  • Examples XIII through XVI are hair rinse compositions having the same compositions as disclosed above for Examples IX through XII, respectively, made with the following method.
  • Examples XIII through XVI have many advantages. For example, they can provide good spreadability and good rinsability when the wet hair, and also show good combing feel and lustery appearance when the hair is dry.
  • Lactic acid LACTIC ACID obtained by Showa Kako *3
  • Acetic acid ACETIC ACID obtained by Denki Kagaku Kogyo *4
  • MALIC ACID obtained by Fuso Kagaku
  • Kathon CG Mixture of methylchloroisothiazoline and methylisothiazoline obtained by Rohm & Haas Co., (Philadelphia, PA, USA).

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Abstract

Cette invention concerne des compositions pour le conditionnement des cheveux, lesquelles comprennent les éléments suivants: (a) de 0,6 à 9,0 % en poids environ d'une amidoamine; (b) de 0,1 à 10,0 % en poids environ d'un acide choisi dans le groupe comprenant de l'acide acétique, de l'acide tartrique, de l'acide fumarique, de l'acide lactique, de l'acide malique, de l'acide succinique ou des mélanges de ces derniers; (c) de 1 à 15 % en poids environ d'un composé qui possède un point de fusion élevé d'au moins 25 °C environ, et qui est choisi dans le groupe comprenant des alcools gras, des acides gras, des dérivés d'alcools gras, des dérivés d'acides gras, des hydrocarbures, des stéroïdes ou des mélanges de ces derniers; et enfin (d), de l'eau. Le pH de cette composition de conditionnement des cheveux varie de 2,5 à 4,5 environ, la composition ne contenant pratiquement pas de composés d'ammonium quaternaire. Cette invention concerne également des procédés appropriés permettant de fabriquer ces compositions de conditionnement.
PCT/US1997/014161 1997-08-29 1997-08-29 Compositions pour le conditionnement des cheveux WO1999011226A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP10541591A JP2000507976A (ja) 1997-08-29 1997-08-29 ヘアコンディショニング組成物
BR9714855-5A BR9714855A (pt) 1997-08-29 1997-08-29 Composições condicionadoras de cabelos
EP97940551A EP1011611A1 (fr) 1997-08-29 1997-08-29 Compositions pour le conditionnement des cheveux
PCT/US1997/014161 WO1999011226A1 (fr) 1997-08-29 1997-08-29 Compositions pour le conditionnement des cheveux
AU42302/97A AU4230297A (en) 1997-08-29 1997-08-29 Hair conditioning compositions

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001047480A1 (fr) * 1999-12-24 2001-07-05 Henkel Kommanditgesellschaft Auf Aktien Produits pour les soins de la peau et des cheveux
EP1428497A1 (fr) * 2002-12-12 2004-06-16 KPSS-Kao Professional Salon Services GmbH Composition de prétraitment des cheveux avant coloration à l'aide des colorants directs acides
WO2009084217A1 (fr) 2007-12-28 2009-07-09 Kao Corporation Composition cosmétique capillaire
EP2332517A1 (fr) 2005-04-05 2011-06-15 Kao Corporation Agent pour le traitement des cheveux
EP3380200A4 (fr) * 2015-11-24 2019-07-17 L'oreal Compositions pour le traitement des cheveux
US10828244B2 (en) 2015-11-24 2020-11-10 L'oreal Compositions for treating the hair
EP3812010A1 (fr) * 2019-10-25 2021-04-28 Unilever PLC Compositions pour le conditionnement des cheveux
US10993896B2 (en) 2015-05-01 2021-05-04 L'oreal Compositions for altering the color of hair
US11083675B2 (en) 2015-11-24 2021-08-10 L'oreal Compositions for altering the color of hair
US11090249B2 (en) 2018-10-31 2021-08-17 L'oreal Hair treatment compositions, methods, and kits for treating hair
US11135150B2 (en) 2016-11-21 2021-10-05 L'oreal Compositions and methods for improving the quality of chemically treated hair
US11419809B2 (en) 2019-06-27 2022-08-23 L'oreal Hair treatment compositions and methods for treating hair
US11433011B2 (en) 2017-05-24 2022-09-06 L'oreal Methods for treating chemically relaxed hair
US11596588B2 (en) 2017-12-29 2023-03-07 L'oreal Compositions for altering the color of hair

Families Citing this family (6)

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Publication number Priority date Publication date Assignee Title
TWI278328B (en) 2000-07-21 2007-04-11 Kao Corp Hair cosmetic composition
JP2003146846A (ja) * 2001-11-14 2003-05-21 Kao Corp 毛髪処理剤組成物
DE102004049344A1 (de) * 2004-10-08 2006-04-13 Basf Ag Stabilisierung von wässrigen Lösungen von Homo- und Copolymeren des N-Vinylpyrrolidons
JP5619409B2 (ja) * 2009-12-10 2014-11-05 株式会社ミルボン 毛髪処理剤
JP5969272B2 (ja) * 2012-06-08 2016-08-17 東邦化学工業株式会社 毛髪用組成物
JP6718706B2 (ja) * 2016-03-15 2020-07-08 花王株式会社 毛髪化粧料

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EP0562639A1 (fr) * 1992-03-27 1993-09-29 Helene Curtis, Inc. Compositions de shampoings et agent de suspension pour ces compositions
DE4232506A1 (de) * 1992-09-29 1994-03-31 Henkel Kgaa Haarbehandlungsmittel
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WO1995020939A1 (fr) * 1994-02-02 1995-08-10 The Procter & Gamble Company Compositions de soins pour les cheveux contenant un alcool gras a point de fusion peu eleve et un polymere d'oxyde d'ethylene/oxyde de propylene

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EP0562639A1 (fr) * 1992-03-27 1993-09-29 Helene Curtis, Inc. Compositions de shampoings et agent de suspension pour ces compositions
DE4232506A1 (de) * 1992-09-29 1994-03-31 Henkel Kgaa Haarbehandlungsmittel
JPH0761911A (ja) * 1993-08-24 1995-03-07 Hoyu Co Ltd 毛髪処理剤
WO1995020939A1 (fr) * 1994-02-02 1995-08-10 The Procter & Gamble Company Compositions de soins pour les cheveux contenant un alcool gras a point de fusion peu eleve et un polymere d'oxyde d'ethylene/oxyde de propylene

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6620409B2 (en) 1999-12-24 2003-09-16 Henkel Kommanditgesellschaft Auf Aktien Hair and skin care agents
WO2001047480A1 (fr) * 1999-12-24 2001-07-05 Henkel Kommanditgesellschaft Auf Aktien Produits pour les soins de la peau et des cheveux
EP1428497A1 (fr) * 2002-12-12 2004-06-16 KPSS-Kao Professional Salon Services GmbH Composition de prétraitment des cheveux avant coloration à l'aide des colorants directs acides
EP2332517A1 (fr) 2005-04-05 2011-06-15 Kao Corporation Agent pour le traitement des cheveux
US8197800B2 (en) * 2005-04-05 2012-06-12 Kao Corporation Hair treating agent
WO2009084217A1 (fr) 2007-12-28 2009-07-09 Kao Corporation Composition cosmétique capillaire
US10993896B2 (en) 2015-05-01 2021-05-04 L'oreal Compositions for altering the color of hair
US11083675B2 (en) 2015-11-24 2021-08-10 L'oreal Compositions for altering the color of hair
US10828244B2 (en) 2015-11-24 2020-11-10 L'oreal Compositions for treating the hair
EP3380200A4 (fr) * 2015-11-24 2019-07-17 L'oreal Compositions pour le traitement des cheveux
US11191706B2 (en) 2015-11-24 2021-12-07 L'oreal Compositions for altering the color of hair
US11213470B2 (en) 2015-11-24 2022-01-04 L'oreal Compositions for treating the hair
US12048759B2 (en) 2015-11-24 2024-07-30 L'oreal Compositions for treating the hair
US11135150B2 (en) 2016-11-21 2021-10-05 L'oreal Compositions and methods for improving the quality of chemically treated hair
US11433011B2 (en) 2017-05-24 2022-09-06 L'oreal Methods for treating chemically relaxed hair
US11596588B2 (en) 2017-12-29 2023-03-07 L'oreal Compositions for altering the color of hair
US11090249B2 (en) 2018-10-31 2021-08-17 L'oreal Hair treatment compositions, methods, and kits for treating hair
US11975092B2 (en) 2018-10-31 2024-05-07 L'oreal Hair treatment compositions, methods, and kits for treating hair
US11419809B2 (en) 2019-06-27 2022-08-23 L'oreal Hair treatment compositions and methods for treating hair
EP3812010A1 (fr) * 2019-10-25 2021-04-28 Unilever PLC Compositions pour le conditionnement des cheveux

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