CA2229929A1 - Hair treatment composition - Google Patents

Hair treatment composition Download PDF

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Publication number
CA2229929A1
CA2229929A1 CA 2229929 CA2229929A CA2229929A1 CA 2229929 A1 CA2229929 A1 CA 2229929A1 CA 2229929 CA2229929 CA 2229929 CA 2229929 A CA2229929 A CA 2229929A CA 2229929 A1 CA2229929 A1 CA 2229929A1
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Prior art keywords
composition
hair
weight
fatty acid
composition according
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CA 2229929
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French (fr)
Inventor
Walter Thomas Gibson
Gillian Elizabeth Westgate
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Unilever PLC
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Unilever PLC
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners
    • 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
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • 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
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/731Cellulose; Quaternized cellulose derivatives
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/737Galactomannans, e.g. guar; Derivatives thereof
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions 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
    • A61K8/8152Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/892Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/896Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/899Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing sulfur, e.g. sodium PG-propyldimethicone thiosulfate copolyol
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • 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
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426Polymers characterized by specific structures/properties characterized by the charge cationic

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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)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

A hair treatment composition for the supply of precursors of hair integral lipid fatty acids to the hair follicle comprising:

(i) a first fatty acid precursor which is an amino acid selected from leucine, isoleucine, methionine and valine, and mixtures thereof, which precursor is present at levels of from 0.01 to 20% by weight based on the total weight of the composition, and from 20% to 100% by weight based on the total weight of amino acids present in the composition, (ii) from 0.01% to 20% by weight of a second fatty acid precursor selected from sugars, mono-, di-, and tri-carboxylic acids and salts thereof, which second fatty acid precursor is able to donate a two or three-carbon unit for fatty acid chain elongation, (iii) at least one surfactant selected from anionic, amphoteric, zwitterionic and cationic surfactants and mixtures thereof.

Description

. CA 02229929 l998-02-l9 HAIR TREATMENT COMPOSITION

FIELD OF THE INVENTION

This invention relates to hair treatment compositions, containing precursors of hair integral lipid fatty acids and the use of the compositions for enhancing physical properties of the hair fibre such as in particular shine, smoothness, manageability, softness and cuticle integrity.

BACKGROUND OF THE INVENTION

Branched and straight chain integral lipids are believed to play an important role in the structure and integrity of the hair fibre, especially with respect to its surface properties.
The lipids are present at the fibre surface, bound to the surface membrane and in the cell membrane complex, and are believed to contribute to fibre shine, smoothness, manageability, softness, protection, lubrication and cuticle integrity.

Surface integral lipids are lost from fibres due to physical and chemical damage incurred inter alia through washing, harsh styling treatments and weathering. This loss has been found to increase fibre roughness and decrease shine. The C21 branched fatty acid - 18-methyleicosanoic acid is thought to be a particularly important component in the lipid profile of the hair. Fatty acid analysis of hair from people with maple syrup urine disease (MSUD) shows that there is only a very small amount of 18-methyleicosanoic acid present, compared to that found in normal controls. The same analysis also indicates that there were decreases in other branched chain fatty acids (C17:Obr, Cl9:Obr, C20:Obr). There was also an increase in unbranched saturated fatty acids (C16:0, C18:0, C20:0, C22:0 and C24:0) [Jones et al, Journal of Investigative Dermatology, 104(4) 1995, 688]. Hairs from patients with MSUD
show a structural defect in lhe fibre cuticle.

EP-A- O 483 689 relates to a hair cosmetic composition incorporating fatty acid with a specific type of branched chain, in particular 18-methyleicosanoic acid (hereinafter referred to as 18-MEA) and salts and esters thereof. The compositions are said to prevent damage to hair such as split ends, and give soft, smooth and glossy conditioning effects.

However, the branched fatty acids must be obtained either by the separation and extraction from hair or by a multistep chemical process as described in EP-A-O 483 689 involving subjecting appropriate phosphonium salt and aldehyde precursors to the Wittig reaction followed by reduction and hydrolysis.
Straight chain fatty acids such as palmitic acid, have also been added to hair treatment: compositions to improve hair properties.

Exogenous application of free straight or branched chain fatty acid via hair treatment compositions as described above has several disadvantages. Firstly, there is the cost of extraction of the materials from natural sources or chemical synthesis. Moreover, free fatty acids supplied exogenously do not become integral and strongly bound to the fibre, in contrast to the natural ones which are only extractable from the fibre by alkaline hydrolysis. Natural hair integral lipids may be covalently bonded to the fibre by a thioester linkage CA 02229929 1998-02-l9 or derivatised into further essential constituents of the fibre such as phospholipids and ceramides.

We have now found that cultured hair follicles can synthesise branched and straight chain fatty acids such as 18-MEA and palmitic, stearic and myristic acid if supplied with specific nutrients which are carbon donors for fatty acid chain elongation. These specific nutrients are selected from particular amino acids, sugars, and organic carboxylic acids and their salts.

Amino acids are known to be important for the nourishment of the human hair root and the ~rowth of human hair.

GB 1 401 089 describes hair treatment compositions containing natural amino acids or protein hydrolyates. Particularly preferred are glycine, glutamic acid, aspartic acid, lysine, serine and alanine, for the reason that these amino acids are naturally found combined, in the form of polypeptides, in the substances collagen and keratin which occur as structural components of human skin and hair. A shampoo composition is described which incorporates protein hydrolysates resulting from the complete hydrolysis of collagen.

EP 0 186 025 discloses cosmetic preparations for care of skin and hair with a hydrolysate of almond protein. Almond protein is characterised by a high content of acidic and basic amino acids and contains 40-50 wt% glutamic acid, aspartic acid and arginine.
Numerous publications describe the use of an array of amino acids, often in Hcocktail" form, in lotions or tonics for topical application to cure baldness and other skin, scalp and hair disorders. Examples of such disclosures are JP 59/007,111 which relates to a hair cosmetic with dandruff-preventing properties containing vitamin E acetate and methionine, CA
888,689 which describes hair and scalp preparations for normalisation of scalp secretions and promotion of hair growth which may contain, inter alia, cysteine and methionine in a base incorporating bergamot oil and nonionic emulsifier, and WO 92/00720 which describes a composition containing L-leucine, L-isoleucine and L-valine, said to stimulate growth and regeneration of hair and nails.

The prior art discussed above does not address the biosynthesis of hair integral lipid fatty acids in hair follicles.

SUM~L~RY OF THE INVENTION

The present invention provides a hair treatment composition for the supply of precursors of hair integral lipid fatty acids to the hair follicle comprising:

(i) a first fatty acid precursor which is an amino acid selected from leucine, isoleucine, methionine and valine, and mixtures thereof, which precursor is present at levels of from 0.01 to 20% by weight based on the total weight of the composition, and from 20% to 100% by weight based on the total weight of amino acids present in the composition, (ii) from 0.01% to 20% by weight of a second fatty acid precursor selected from sugars, mono-, di-, and tri-- carboxylic acids and salts thereof, which second fatty acid precursor is able to donate a two or three-carbon unit for fatty acid chain elongation, (iii) at least one surfactant selected from anionic, amphoteric, zwitterionic and cationic surfactants and mixtures thereof.

DETAILED DESCRIPTION OF THE lNV~ lON

Isoleucine is the most preferred amino acid (i) for compositions of the invention. It is thought, whilst not wishing to be bound by any theory, that this is the most direct precursor for 18-MEA synthesis in the hair follicle, 18-MEA being a particularly important component in the lipid profile of the hair fibre. Some proposed biochemical pathways have been given in the literature but are not yet well elucidated.

The amino acid (i) is thought to supply the branch point for hair integral lipid branched chain fatty acid. It may also be catabolized in the hair follicle to form precursors of hair integral lipid straight chain fatty acids.

Simple derivatives of the amino acid (i) may be employed, such as salts and hydrosalts. It is further possible to employ other derivatives such as acyl, ester and peptide derivatives.
These too may be used as salts or hydrosalts.

Examples are N-alkanoyl derivatives in which the alkanoyl moiety has an alkyl chain length of from 3 to 20 carbon atoms, preferably from 4 to 10 carbon atoms, eg N-butanoyl, N-hexanoyl and N-octanoyl, N-alkyl or COO-alkyl derivatives in which the alkyl group is straight chain and from 1 to 20 carbon atoms, preferably from 1 to 4 carbon atoms, eg methyl, ethyl and n-propyl and peptide derivatives in which the CA 02229929 l998-02-l9 peptide residue comprises from 2 to 8 amino acid residues or substituted amino acid residues.

Mixtures of amino acids may be used, such as may be obtained from a protein hydrolysate. However, such a mixture must be judiciously selected to ensure that from 20% to 100~ by weight based on the total weight of amino acids present in the resultant composition is constituted by one or a mixture of the specific amino acids (i).
Preferably, from 90~ to 100% by weight based on the total weight of amino acids present in the resultant composition is consituted by one or a mixture of the specific amino acids (i). a single amino acid of the amino acids (i) is used. Most Component (ii) is a second fatty acid precursor selected from sugars, mono-, di-, and tri-carboxylic acids and salts thereof, which second fatty acid precursor is able to donate a two or three-carbon unit for fatty acid chain elongation.
The two or three carbon unit itself may be sourced directly from the molecule, or derived indirectly through catabolism of the molecule.

Examples of sugars for component (ii) are sucrose, fructose and glucose. Glucose is particularly preferred. Examples of mono-, di-, and tri-carboxylic acids are acetic acid, malonic acid, lactic acid, citric acid, and propionic acid. Suitable salts of these acids are those from which the a two or three-carbon unit for fatty acid chain elongation can be derived from the acid moiety in a bioavailable form. Examples of such salts are the water-soluble alkali metal, alkaline earth metal and ammonium salts (including substituted ammonium salts) of these acids.

CA 02229929 l998-02-l9 We have shown that these components (ii) when used alone can contribute to straight chain fatty acid biosynthesis in the hair follicle. Two (eg acetate, lactate) and three (eg propionate) carbon donors are thought to yield even and odd carbon chain number fatty acids respectively via chain elongation.

In combination with the amino acid component (i), precursors for straight and branched chain fatty acids can be supplied (the amino acid moiety supplying the branch point as discussed above), which is advantageous since key hair integral lipids have been found to derive from both straight and branched chain fatty acids.

The total amount of amino acid (i) and carbon donor (ii)in the compositions of the invention ranges from 0.01% to 20% by weight of the composition, preferably from 0.02% to 5%, most preferably from 0.05% to 2% for either active.

The ratio of components (i) to (ii) is such as to obtain a complementary action of amino acid and carbon donor so as to supply a suitable balance of straight and branched chain fatty acid precursors. The particular ratio will depend on the hair condition and the specific actives employed. The ratio of (i) to (ii) is generally in the range of 10:1 to 1:10, preferably 3:1 to 1: 3, most preferably 1:1.

Advantageously, the composition of the invention can be formulated as a shampoo and will then accordingly comprise one or more cleansing surfactants which are cosmetically ~' acceptable and suitable for topical application to the hair.

CA 02229929 l998-02-l9 Suitable cleansing surfactants, which may be used singularly or in combination, are selected from anionic, amphoteric and zwitterionic surfactants, and mixtures thereof.

Examples of anionic surfactants are the alkyl sulphates, alkyl ether sulphates, alkaryl sulphonates, alkanoyl isethionates, alkyl succinates, alkyl sulphosuccinates, N-alkyl sarcosinates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, and alpha-olefin sulphonates, especially their sodium, magnesium, ammonium and mono-, di- and triethanolamine salts. The alkyl and acyl groups generally contain from 8 to 18 carbon atoms and may be unsaturated. The alkyl ether sulphates, alkyl ether phosphates and alkyl ether carboxylates may contain from 1 to 10 ethylene oxide or propylene oxide units per molecule.

Typical anionic surfactants for use in shampoos of the invention include sodium oleyl succinate, ammonium lauryl sulphosuccinate, ammonium lauryl sulphate, sodium dodecylbenzene sulphonate, triethanolamine dodecylbenzene sulphonate, sodium cocoyl isethionate, sodium lauryl isethionate and sodium N-lauryl sarcosinate. The most preferred anionic surfactants are sodium lauryl sulphate, triethanolamine monolauryl phosphate, sodium lauryl ether sulphate 1 EO, 2EO and 3EO, ammonium lauryl sulphate and ammonium lauryl ether sulphate lEO, 2EO and 3EO.

Examples of amphoteric and zwitterionic surfactants include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulphobetaines (sultaines), alkyl glycinates, alkyl carboxyglycinates,alkyl amphopropionates, alkylamphoglycinates, alkyl amidopropyl hydroxysultaines, acyl taurates and acyl glutamates, wherein the alkyl and acyl CA 02229929 l998-02-l9 groups have from 8 to 19 carbon atoms. Typical amphoteric and zwitterionic surfactants for use in shampoos of the invention include lauryl amine oxide, cocodimethyl sulphopropyl betaine and preferably lauryl betaine, cocamidopropyl betaine and sodium cocamphopropionate.

The cleansing surfactant(s) ~lay be present in shampoo compositions of the invention in a total amount of from about 1 to about 40% by weight based on the total weight of the shampoo composition, preferably from about 2 to about 30% by weight, optimally from about 10% to 30% by weight.

The shampoo can also include nonionic surfactants to help impart aesthetic, physical or cleansing properties to the composition. The nonionic surfactant can be included in an amount ranging from 0% to about 5% by weight based on total weight.

For example, representative nonionic surfactants that can be included in shampoos of the invention include condensation products of aliphatic (C8 - Cl8) primary or secondary linear or branched chain alcohols or phenols with alkylene oxides, usually ethylene oxide and generally having from 6 to 30 ethylene oxide groups.
Other representative nonionics include mono- or di-alkyl alkanolamides. Examples include coco mono- or di-ethanolamide and coco mono-isopropanolamide.

Further nonionic surfactants which can be included in shampoos '~ for the invention are the alkyl polyglycosides (APGs).
Typically, the APG is one which comprises an alkyl group connected (optionally via a bridging group) to a block of one CA 02229929 l998-02-l9 or more glycosyl groups. Preferred APGs are defined by the following formula:

RO - (G) n wherein R is a branched or straight chain alkyl group which may be saturated or unsaturated and G is a saccharide group.

R may represent a mean alkyl chain length of from about C5 to about C20. Preferably R represents a mean alkyl chain length of from about C8 to about Cl2. Most preferably the value of R
lies between about 9.5 and about 10.5. G may be selected from Cs or C6 monosaccharide residues, and is preferably a glucoside. G may be selected from the group comprising glucose, xylose, lactose, fructose, mannose and derivatives thereof. Preferably G is glucose.

The degree of polymerisation, n, may have a value of from about 1 to about 10 or more. Preferably, the value of n lies in the range of from about 1.1 to about 2. Most preferably the value of n lies in the range of from about 1. 3 to about 1.5.

Suitable alkyl polyglycosides for use in the invention are commercially available and include for example those materials identified as: Oramix NS10 ex Seppic; Plantaren 1200 and Plantaren 2000 ex Henkel.

Likewise the composition can include other emulsifiers, conditioning agents, inorganic salts, humectants and similar materials to provide the composition with desirable aesthetic or physical properties.

CA 02229929 l998-02-l9 Representative conditioning agents that can be included in shampoos of the invention include silicones. Typically these are present in the composition at a level of from 0.01% to 10~, preferably from 0.5 to 5~, by weight based on total weight.

Silicones are particularly preferred conditioning agents for hair. Representative silicones include volatile and non-volatile silicones, such as for example polyalkylsiloxanes (optionally end-capped with one or more hydroxyl groups), polyalkylaryl siloxanes, siloxane gums and resins, cyclomethicones, aminofunctional silicones, quaternary silicones and mixtures thereof.

Preferred silicones include polydimethylsiloxanes (of CTFA
designation dimethicone) and hydroxylated polydimethylsiloxanes (of CTFA designation dimethiconol).
Suitably the average particle size of the silicone in the shampoo composition is less than 20 microns and preferably less than 2 microns. Particle size may be measured by means of a light scattering technique, using a 2600D Particle Sizer from Malvern Instruments. The silicone is preferably emulsion-polymerised, since this enables silicones of very high viscosity to be more easily processed. The silicone can be cross-linked.

Silicones of the above types are widely available commercially, for example as DC-1784 and DCX2-1391, both ex Dow Corning.

Shampoo compositions of the invention may also include a polymeric cationic conditioning compound that is substantive to the hair and imparts conditioning properties to the hair.

The polymeric cationic conditioning compound will generally be present at levels of from 0.01 to 5%, preferably from about 0.05 to 1%, more preferably from about 0.08% to about 0.5% by weight. Synthetic or naturally derived polymers having a quaternised nitrogen atom are useful. The molecular weight of the polymer will generally be between 5 000 and 10 000 000, typically at least 10 000 and preferably in the range 100 000 to about 2 000 000.
Representative synthetic quaternised polymers include, for example: cationic copolymers of 1-vinyl-2-pyrrolidine and 1-vinyl-3-methyl-imidazolium salt (e.g., Chloride salt) (referred to in the industry by the Cosmetic, Toiletry, and Fragrance Association, HCTFA". as Polyquaternium-16);
copolymers of 1-vinyl-2-pyrrolidine and dimethylaminoethyl methacrylate (referred to in the industry by CTFA as Polyquaternium-11); cationic diallyl quaternary ammonium-containing polymers including, for example, dimethyldiallylammonium chloride homopolymer (referred to in the industry (CTFA) as Polyquaternium 6); mineral acid salts of amino-alkyl esters of homo-and co-polymers of unsaturated carboxylic acids having from 3 to 5 carbon atoms, as described in U.S. Patent 4,009,256; ancl cationic polyacrylamides as described in WO95/22311.

Representative naturally-derived quaternised polymers include quaternised cellulosic compounds and cationic guar gum derivatives, such as guar hydroxypropyltrimonium chloride.
Examples are JAGUAR C-13S, JAGUAR C-15, and JAGUAR-C17, commercially available from Meyhall in their JAGUAR trademark series.

CA 02229929 l998-02-l9 The shampoo composition of the invention can also include optional conditioning agents such as branched chain fatty acids, such as 18-MEA, or straight chain fatty acids such as palmitic, myristic and/or stearic acids. In general these ingredients can be included in an amount ranging from 0% to about 3~ by weight based on t:otal weight.

Compositions in accordance with the invention may also be formulated as a hair conditioner for the treatment of hair (typically after shampooing) and subsequent rinsing. Such formulations will then accordingly comprise one or more conditioning surfactants which are cosmetically acceptable and suitable for topical application to the hair.

Suitable conditioning surfactants are selected from cationic surfactants, used singly or in admixture. Examples include quaternary ammonium hydroxides or salts thereof, e.g chlorides.

Suitable cationic surfactants for use in hair conditioners of the invention include cetyltrimethylammonium chloride, behenyltrimethylammonium chloride, cetylpyridinium chloride, tetramethylammonium chloride, tetraethylammonium chloride, octyltrimethylammonium chloride, dodecyltrimethylammonium chloride, hexadecyltrimethylammonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, didodecyldimethylammonium chloride, dioctadecyldimethylammonium chloride, tallowtrimethylammonium chloride, cocotrimethylammonium chloride, and the corresponding hydroxides thereof. Further suitable cationic surfactants include those materials having the CTFA

- ~4 -designations Quaternium-5, Quaternium-31 and Quaternium-18.
Mixtures of any of the foregoing materials may also be suitable. A particularly useful cationic surfactant for use in hair conditioners of the invention is cetyltrimethylammonium chloride, available commercially, for example as GENAMIN CTAC, ex H~echst Celanese.

In hair conditioners of the invention, the level of cationic surfactant is preferably from 0.01 to 10%, more preferably 0.05 to 5%, most preferably 0.1 to 2% by weight of the composition.

Conditioners of the invention advantageously incorporate a fatty alcohol material. The combined use of fatty alcohol materials and cationic surfactants in conditioning compositions is believed to be especially advantageous, because this leads to the formation of a lamellar phase, in which the cationic surfactant is dispersed.

Representative fatty alcohols comprise from 8 to 22 carbon atoms, more preferably 16 to 20. Examples of suitable fatty alcohols include cetyl alcohol, stearyl alcohol and mixtures thereof.

The level of fatty alcohol materials is conveniently from 0.01 to 10%, preferably from 0.1 to 5% by weight of the composition. The weight ratio of cationic surfactant to fatty alcohol is suitably from 10:] to 1:10, preferably from 4:1 to 1:8, optimally from 1:1 to 1:4.
Conditioners of the invention can include other emulsifiers, conditioning agents, inorganic salts, humectants and similar materials to provide the composition with desirable aesthetic CA 02229929 l998-02-l9 - :L5 -or physical properties. Silicones, as described above for shampoo compositions, are particularly preferred conditioning agents for hair.

As further optional components for inclusion in shampoo or conditioner compositions of the invention, in addition to water, may be mentioned the following conventional adjunct materials known for use in cosmetic compositions: suspending agents, thickeners, pearlescing agents, opacifiers, salts, perfumes, buffering agents, colouring agents, emollients, moisturisers, foam stabilisers, sunscreen materials, antimicrobial agents, preservatives, antioxidants, natural oils and extracts, propellants.

The compositions of the invention are primarily intended for topical application to the hair and/or scalp of a human subject to improve hair fibre surface properties such as smoothness, softness, manageability, cuticle integrity, and, in particular shine.
The invention accordingly provides the use of a composition as defined above for enhancing at least one of the following hair surface properties: shine, smoothness, manageability, softness and cuticle integrity.
Components (i) and (ii) may also be used independently, in suitable amounts as described above, in a hair treatment composition to supply hair integral lipid fatty acid precursors to the hair follicle.
Accordingly, the invention also provides the use of (i) or (ii) in a hair treatment composition as hair integral lipid fatty acid precursors for enhancing at least one of the CA 02229929 l998-02-l9 following hair fibre surface properties: shine, smoothness, manageability, softness and cuticle integrity.

The invention will now be further illustrated by the following, non-limiting Examples.

Demonstration of incorporation of isoleucine into lipids by human hair follicles in vitro Human hair follicles were isolated by the method of Philpott et al (1990, J Cell Sci 97: 463-470) and cultured in the presence of radiolabelled isoleucine. The follicles were incubated for 2 days at 37~C, 5% C02 in air and >95% humidity.

At the end of the total incubation period, the lipid content of the follicles was extracted and analysed.

The results showed clearly that the major labelled species was 18MEA (The identity of the other radiolabelled species was not determined.

Demonstration of incorporation of acetate into lipids by human hair follicles in vitro Follicles were isolated as described in example 1 and cultured in the presence of radiolabelled acetate. The follicles were incubated for 3 days in conditions stated above for example 1.

At the end of the total incubation period, the lipid content of the follicles was extracted and analysed.

The results showed clearly that the major labelled species (in decreasing order of amount of radiolabel present) were;
palmitic, stearic, myristic, arachidic acids and 18-MEA. The identity of the other species was not determined.

Demonstration of incorporation of glucose into lipids by human hair follicles in vitro Follicles were isolated as described in example 1 and cultured in the presence of radiolabelled glucose. The follicles were incubated for 2 days in conditions stated above for example 1.

At the end of the culture period, the lipids were extracted as described above in example 1.
The results showed clearly that the major labelled species (in decreasing order of amount of radiolabel) were: 18MEA, palmitic and stearic acids.

EXAMPLES 4 and 5 The following formulations illustrate shampoo compositions according to the invention.

Ingredient %(by weight based on total weight) Ex.4 Ex.5 Sodium lauryl ether 20 20 - ~8 -sulphate(2EO);70%active Cocamidopropylbetaine 6.67 6.4 5 Sodium benzoate 0.5 0.5 Perfume 0.55 0-55 Vitamin E acetate 0.05 0.05 Titanium dioxide coated mica (TIMIRON MP 1001 ex Merck) 0.2 0.2 Silicone emulsion 0. 8 0.4 15 (DC 1784 ex Dow Corning) Guar hydroxypropyltrimonium 0.1 0.1 chloride (JAGUAR C13S ex Meyhall) Citric acid 0.42 0.42 Sodium chloride 0.7 0.7 Sodium hydroxide 0.15 0.15 L-Isoleucine 0.1 0.1 D-Glucos e 0.1 0.1 CARBOPOL 9 80 0.4 0. 4 (Crosslinked polyacrylate ex BF Goodrich) . CA 02229929 l998-02-l9 _ ~ g _ Water to 100% to 100%

The shampoos of Examples 4 and 5 were both opacified liquids of viscosity 4000 to 6000 cps and pH 4.5 to 5.
S

EXAMPLES 6 and 7 The following formulations illustrate further shampoo compositions according to the invention.

Ingredient %(by weic~ht based on total weight) Ex.6 Ex.7 Sodium lauryl ether 20 20 sulphate(2EO);70%active Cocamidopropylbetaine 6.67 6.66 Sodium benzoate 0.5 0.5 Perfume 0-55 0 55 Vitamin E acetate 0.05 0.05 Titanium dioxide coated mica ~TIMIRON MP 1001 ex Merck) 0.2 30 Silicone emulsion 4.0 (DC 1784 ex Dow Corning) Guar hydroxypropyltrimonium 0.1 0.05 CA 02229929 l998-02-l9 chloride(JAGUAR C13S ex Meyhall) Citric acid 0.5 0,5 5 Sodium chloride 0.8 0.8 Sodium hydroxide 0.2 0.05 L-Isoleucine 0.1 0.1 D-Glucose 0.1 0.1 CARBOPOL 980 0.4 (Crosslinked polyacrylate 15 ex BF Goodrich) Water to 100% to 100%

The shampoos of Examples 6 and 7 were liquids of viscosity 3500 to 5000 cps and pH 4.5 t:o 5. Example 6 was opacified and Example 7 was clear.

The shampoos of Examples 4-7 all imparted excellent shine and smoothness to the hair.

EXAMPLES 8 and 9 The following formulations i:Llustrate post-wash hair conditioning compositions according to the invention.

CA 02229929 l998-02-l9 Ingredient %(by weiyht based on total weight) Ex.8 Ex.9 Cetyl trimethylammonium 5 chloride 2.4 2.4 Cetearyl alcohol 3.0 2. 3 Paraffin 52/54 1.00 Glyceryl stearate 0.7 Silicone emulsion 3.0 3.0 15 (DC 1784 ex Dow Corning) Hydrophobically modified - 0.03 hydroxyethylcellulose (POLYSURF 67 ex Aqualon) Perfume 0.5 0-5 Vitamin E acetate 0.05 0.05 25 Preservative 0.2 0.2 Phenoxyethanol 0.4 L-Isoleucine 0.1 0.1 D-Glucose 0.1 0.1 Citric acid - 0.025 CA 02229929 l998-02-l9 Water to 100% to 100%

The conditioner of Example 8 had a pH of 4.5-5.0 and that of Example 9 had a pH of 3.0 to 3.5. Both were opacified liquids of viscosity 7000-11000 cps.

Both conditioners imparted excellent shine and smoothness to shampooed hair.

Claims (13)

1. A hair treatment composition for the supply of precursors of hair integral lipid fatty acids to the hair follicle comprising:

(i) a first fatty acid precursor which is an amino acid selected from leucine, isoleucine, methionine and valine, and mixtures thereof, which precursor is present at levels of from 0.01 to 20% by weight based on the total weight of the composition, and from 20% to 100% by weight based on the total weight of amino acids present in the composition, (ii) from 0.01% to 20% by weight of a second fatty acid precursor selected from sugars, mono-, di-, and tri-carboxylic acids and salts thereof, which second fatty acid precursor is able to donate a two or three-carbon unit for fatty acid chain elongation, (iii) at least one surfactant selected from anionic, amphoteric, zwitterionic and cationic surfactants and mixtures thereof.
2. A composition according to claim 1, in which (i) is isoleucine.
3. A composition according to claim 1 or 2, in which (ii) is glucose.
4. A composition according to any of claims 1 to 3, in which the amount of amino acid (i) is from 0.01% to 20% by weight of the composition.
5. A composition according to any of claims 1 to 4, in which the amount of two-carbon donor (ii) is from 0.01% to 20% by weight of the composition.
6. A composition according to any of claims 1 to 5, in which the ratio of (i) to (ii) is in the range of from 10:1 to 1:10.
7. A composition according to any of claims 1 to 6, which is formulated as a shampoo composition, and in which the at least one surfactant is present in a total amount of from 0.1 to 50%
by weight of the composition.
8. A composition according to claim 7, which further comprises a polymeric cationic conditioning compound and/or a silicone.
9. A composition according to any one of claims 1 to 6, which is formulated as a hair conditioner, and in which the at least one surfactant is a cationic surfactant present in a total amount of from 0.1 to 10% by weight of the composition.
10. A composition according to claim 9, which further comprises a fatty alcohol.
11. The use of a composition as defined in any of claims 1 to 10 for enhancing at least one of the following hair fibre surface properties: shine, smoothness, manageability, softness and cuticle integrity.
12. The use of (i) or (ii) as hair integral lipid fatty acid precursors in a hair treatment composition for enhancing at least one of the following hair fibre surface properties:
shine, smoothness, manageability, softness and cuticle integrity.
13. The hair treatment composition as claimed in claim 1 and substantially as described herein.
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FR2760189A1 (en) 1998-09-04
GB2322550B (en) 2000-10-04
CN1250190C (en) 2006-04-12
IT1302072B1 (en) 2000-07-20
JPH10236927A (en) 1998-09-08
DE19808395A1 (en) 1998-09-03
AR011891A1 (en) 2000-09-13
CN1195517A (en) 1998-10-14
GB9803144D0 (en) 1998-04-08
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GB9704050D0 (en) 1997-04-16
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ITTO980157A1 (en) 1999-08-26

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