WO2012119810A2 - Composition - Google Patents

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Publication number
WO2012119810A2
WO2012119810A2 PCT/EP2012/051256 EP2012051256W WO2012119810A2 WO 2012119810 A2 WO2012119810 A2 WO 2012119810A2 EP 2012051256 W EP2012051256 W EP 2012051256W WO 2012119810 A2 WO2012119810 A2 WO 2012119810A2
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WO
WIPO (PCT)
Prior art keywords
dye
reactive
hair
polymer
composition according
Prior art date
Application number
PCT/EP2012/051256
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English (en)
Other versions
WO2012119810A3 (fr
Inventor
Stephen Norman Batchelor
Original Assignee
Unilever Plc
Unilever N.V.
Hindustan Unilever Limited
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 Unilever Plc, Unilever N.V., Hindustan Unilever Limited filed Critical Unilever Plc
Priority to EP12708737.7A priority Critical patent/EP2683353A2/fr
Priority to BR112013022596A priority patent/BR112013022596A2/pt
Priority to CN2012800124516A priority patent/CN103415279A/zh
Publication of WO2012119810A2 publication Critical patent/WO2012119810A2/fr
Publication of WO2012119810A3 publication Critical patent/WO2012119810A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • 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
    • A61K8/91—Graft copolymers
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
    • 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
    • A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances

Definitions

  • the present invention relates to a hair care composition comprising a polymer dye and a method for dying the hair.
  • FR 2 456 764 discloses quaternary amine polymer linked to dyes for the colouration of hair.
  • the dyes used do not carry negatively charged substituents that can produce dark shades.
  • WO2008/009579 (Ciba) and WO2009/090121 to WO2009/090125 (BASF) disclose cationic dyes covalently linked to polymers for the colouration of hair.
  • Co-pending Unilever application WO201 1 /1 13680 discloses hair dye compositions comprising a positively charged polymer covalently bound to a negatively charged reactive dye. However the specific reactive dyes of the present invention are not disclosed.
  • the present invention relates to a hair dye composition
  • a hair dye composition comprising a polymer dye, the polymer dye comprising a positively charged polymer covalently bound to a negatively charged reactive dye in which the reactive dye is a bis-azo dye of the structure:
  • a ring is substituted by at least one heterocyclic reactive group and/or a sulphonate group .
  • a method for dying hair by applying to the hair a composition according to the first aspect of the invention.
  • the invention relates to the use of the above described polymer for colouring the hair.
  • compositions of the invention comprise a dye polymer as defined in claim 1
  • a hydrolysed reactive dye is one in which the reactive groups have reacted with the hydroxide anion, HO " , rather than the polymer.
  • the composition contains less than 10Oppm of hydrolysed reactive dye, more preferably less than 5ppm per10 OOOppm of dye polymer present. Most preferably, hydrolysed reactive dyes are not present in the composition. Such dyes may be removed by dialysis.
  • Hydrolysed reactive dyes are not covalently bound to the polymer.
  • a reactive dye that has two reactive groups, where one has reacted with the polymer to form a covalently bond and one has reacted with HO " is not classed as a hydrolysed dye in the context of the invention.
  • the reactive dye of the polymer used in the invention is a blue bis-azo dye of the form:
  • the A ring is substituted by a heterocyclic reactive group and optionally a sulphonate group and the B ring is optionally substituted by groups selected from a heterocyclic reactive group, a sulfooxyethylsulfonyl reactive group, and a sulphonate group.
  • the B ring is substituted by a heterocyclic reactive group.
  • the heterocyclic reactive groups are preferably nitrogen contains aromatic rings bound to a halogen or a quaternary ammonium group, most preferably CI or F, which react with NH 2 or NH groups of the polymers to form a covalent bonds. More preferred heterocylic reactive groups are dichlorotriazinyl, difluorochloropyrimidine, monofluorotrazinyl, monofluorochlorotrazinyl, dichloroquinoxahne, difluorotriazine, monochlorotnazinyl, and trichloropyrimidine.
  • Ri is selected from H or alkyl, preferably H.
  • X is selected from F or CI
  • Z 1 is selected from -CI, -NR 2 R 3 , -OR 2 , -S0 3 Na
  • R 2 and R 3 are independently selected from H, alkyl and aryl groups.
  • Aryl groups are preferably phenyl and are preferably substituted by -S0 3 Na or - S0 2 CH 2 CH 2 OS0 3 Na.
  • Alkyl groups are preferably methyl or ethyl.
  • the heterocylic reactive group is bound at the meta position on the A and B ring.
  • the phenyl groups may be further substituted with suitable uncharged organic groups, preferably with a molecular weight lower than 200.
  • Preferred groups include -CH 3 , -C 2 H 5 , and -OCH 3.
  • the alkyl groups may be further substituted with suitable uncharged organic groups, preferably with a molecular weight lower than 200.
  • Preferred groups include -CH 3 , -C 2 H 5 , -OH, -OCH 3 , -OC 2 H 4 OH.
  • Most preferred heterocylic reactive groups are selected from
  • n 1 or 2, preferably 1 .
  • the reactive dye contains more than one reactive group, preferably two or three.
  • the polymer comprises a free -SH, -OH, -NH or -NH 2 group for reaction with the dye. More preferably, the polymer contains at least one -NH or -NH 2 group, most preferably at least five -NH or -NH 2 group.
  • the polymers have an overall cationic charged at pH 5.0.
  • the polymer comprises quaternary amine groups or tertiary amines.
  • polymers examples include polyethyleneimine, polypropylene- imine, polyvinylamine; polyvinylimine, aminosilcone.
  • the polymer before reaction with the dye, has a weight averaged molecular weight of from 500 to 1000 000, preferably from 800 to 60 000, most preferably from 800 to 2500.
  • the molecular weights are determined by dynamic light scattering using a Zetasizer Nano (Malvern).
  • the polymer is a polyamine.
  • the polyamine is selected from polyethyleneimine, polypropylene- imine, polyvinylamine, and polyvinylimine.
  • Polyamines are polyalkyl amines and are generally linear or branched.
  • the polyamine comprises primary, secondary or tertiary amines or a mixture thereof.
  • the polyamine comprises ethylene alkyl groups and the polymer is formed by ring opening polymerisation of ethyleneimine to provide polyethyleneimine (PEI). PEI is most preferred.
  • the polyamines are alkoxylated to provide alkoxylated PEI's, for example ethoxylated polyethyleneimine (EPEI).
  • EPEI ethoxylated polyethyleneimine
  • a single or a number of amine functions are reacted with one or more alkylene oxide groups to form a polyalkylene oxide side chain.
  • the alkylene oxide can be a homopolymer (for example ethylene oxide) or a random or block copolymer.
  • the PEI's suitable for use in the composition of the invention can have the general formula: (-NHCH2CH2-) X [-N(CH2CH2NH2)CH2CH2-I y wherein x is an integer from about 1 to about 120000, preferably from about 10 to about 20000, more preferably from about 20 to about 10000 and y is an integer from about 1 to about 60000, preferably from about 10 to about 30000, more preferably from about 20 to about 12000.
  • polyethylene imines are PEI-300, PEI-500, PEI 600, PEI- 700, PEI- 800, PEI-1000, PEI-1500, PEI-1800, PEI-2000, PEI-2500, PEI-5000, PEI-10000, PEI-25000, PEI 50000 and PEI-70000, wherein the integer represents the number average molecular weight of the polymer.
  • PEI's which are designated as such are available through Aldrich.
  • the PEI is partially alkoxylated so that at least one NH 2 or NH is available for reaction with the reactive dye, preferably at least one NH 2 .
  • the preferred degree of alkoxylation is from 0.2 to 50% of the primary and secondary amines are alkoxylated.
  • the composition comprises from 0.2 to 10 wt%, most preferably from 0.5 to 3 wt% of the dye polymer.
  • the composition has a pH of from 4 to 1 1 , more preferably from 8 to 10 most preferably from 8.5 to 9.5.
  • the pH may be controlled by the use of common buffers and/or alakli's such as NaOH, NH 4 OH and/or acid such as HCI.
  • compositions of the present invention are formulated into hair colouring compositions which may take a variety of forms, including, for example, mousses, gels, lotions, creams, sprays and tonics. These product forms are well known in the art.
  • the preferred product is a lotion, cream, spray, aerosol mousse or gel.
  • the composition is preferably a hair conditioning composition containing a conditioning active such as a cationic surfactant or silicone, fatty alcohol, fatty acid, fatty ester, fatty amide or mixtures thereof.
  • a conditioning active such as a cationic surfactant or silicone, fatty alcohol, fatty acid, fatty ester, fatty amide or mixtures thereof.
  • suitable conditioning surfactants include those selected from cationic surfactants, used singly or in admixture.
  • the cationic surfactants have the formula N + R 1 R 2 R 3 R 4 wherein R 1 , R 2 , R 3 and R 4 are independently (Ci to C 3 o) alkyl or benzyl.
  • R 1 , R 2 , R 3 and R 4 are independently (Ci to C 3 o) alkyl or benzyl.
  • R 1 , R 2 , R 3 and R 4 are independently (Ci to C 3 o) alkyl or benzyl.
  • one, two or three of R 1 , R 2 , R 3 and R 4 are
  • R 1 , R 2 , R 3 and R 4 group or groups are ( ⁇ - ⁇ - ⁇ ) alkyl or benzyl. More preferably, one or two of R 1 , R 2 , R 3 and R 4 are independently (Ce to C30) alkyl and the other R 1 , R 2 , R 3 and R 4 groups are (C1-C6) alkyl or benzyl groups.
  • the alkyl groups may comprise one or more ester (-OCO- or -COO-) and/or ether (-O-) linkages within the alkyl chain.
  • Alkyl groups may optionally be substituted with one or more hydroxyl groups.
  • Alkyl groups may be straight chain or branched and, for alkyl groups having 3 or more carbon atoms, cyclic.
  • the alkyl groups may be saturated or may contain one or more carbon-carbon double bonds (eg, oleyl).
  • Alkyl groups are optionally ethoxylated on the alkyl chain with one or more ethyleneoxy groups.
  • Suitable cationic surfactants for use in conditioner compositions according to the invention include cetyltrimethylammonium chloride, behenyltrimethylammonium chloride, cetylpyridinium chloride, tetramethylammonium chloride,
  • dodecyltrimethylammonium chloride hexadecyltrimethylammonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, didodecyldimethylammonium chloride, dioctadecyldimethylammonium chloride, tallowtrimethylammonium chloride, dihydrogenated tallow dimethyl ammonium chloride (eg, Arquad 2HT/75 from Akzo Nobel), cocotrimethylammonium chloride, PEG-2-oleammonium chloride and the corresponding hydroxides thereof.
  • dodecyltrimethylammonium chloride hexadecyltrimethylammonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenz
  • cationic surfactants include those materials having the CTFA 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 conditioners according to the invention is cetyltrimethylammonium chloride, available commercially, for example as GENAMIN CTAC, ex Hoechst Celanese.
  • Another particularly useful cationic surfactant for use in conditioners according to the invention is
  • behenyltrimethylammonium chloride available commercially, for example as GENAMIN KDMP, ex Clariant.
  • Another example of a class of suitable cationic surfactants for use in the invention, either alone or together with one or more other cationic surfactants, is a
  • R1 CONH(CH2)mN(R2)R3 in which R 1 is a hydrocarbyl chain having 10 or more carbon atoms,
  • R 2 and R 3 are independently selected from hydrocarbyl chains of from 1 to 10 carbon atoms, and m is an integer from 1 to about 10;
  • hydrocarbyl chain means an alkyl or alkenyl chain.
  • Preferred amidoamine compounds are those corresponding to formula (I) in which R 1 is a hydrocarbyl residue having from about 1 1 to about 24 carbon atoms, R 2 and R 3 are each independently hydrocarbyl residues, preferably alkyl groups, having from 1 to about 4 carbon atoms, and m is an integer from 1 to about 4.
  • R 2 and R 3 are methyl or ethyl groups.
  • m is 2 or 3, i.e. an ethylene or propylene group.
  • Preferred amidoamines useful herein include stearamido-propyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine,
  • arachidamidopropyldiethylamine arachid-amidoethyldiethylamine
  • arachidamidoethyldimethylamine and mixtures thereof.
  • amidoamines useful herein are N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N
  • stearamidopropyldimethylamine stearamidoethyldiethylamine, and mixtures thereof.
  • 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).
  • a protonating acid may be present. Acid may be any organic or mineral acid which is capable of protonating the amidoamine in the conditioner composition. Suitable acids useful herein include hydrochloric acid, 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, hydrochloric acid, fumaric acid, lactic acid and mixtures thereof.
  • the primary role of the acid is to protonate the amidoamine in the hair treatment composition thus forming a tertiary amine salt (TAS) in situ in the hair treatment composition.
  • TAS tertiary amine salt
  • the TAS in effect is a non-permanent quaternary ammonium or pseudo-quaternary ammonium cationic surfactant.
  • the acid is included in a sufficient amount to protonate more than 95 mole% (293 K) of the amidoamine present.
  • the level of cationic surfactant will generally range from 0.01 % to 10%, more preferably 0.05 % to 7.5%, most preferably 0.1 % to 5% by weight of the composition.
  • compositions of the invention can contain, emulsified droplets of a silicone conditioning agent, for enhancing conditioning performance.
  • Suitable silicones include polydiorganosiloxanes, in particular
  • compositions of the invention which have the CTFA designation dimethicone.
  • compositions of the invention are polydimethyl siloxanes having hydroxyl end groups, which have the CTFA designation dimethiconol.
  • silicone gums having a slight degree of cross-linking as are described for example in WO 96/31 188.
  • the viscosity of the emulsified silicone itself (not the emulsion or the final hair conditioning composition) is typically at least 10,000 est at 25 °C the viscosity of the silicone itself is preferably at least 60,000 est, most preferably at least 500,000 est, ideally at least 1 ,000,000 est. Preferably the viscosity does not exceed 10 9 est for ease of formulation.
  • Emulsified silicones for use in the shampoo compositions of the invention will typically have an average silicone droplet size in the composition of less than 30, preferably less than 20, more preferably less than 10 micron, ideally from 0.01 to 1 micron. Silicone emulsions having an average silicone droplet size of £ 0.15 micron are generally termed microemulsions.
  • Emulsified silicones for use in the conditioner compositions of the invention will typically have an size in the composition of less than 30, preferably less than 20, more preferably less than 15.
  • the average silicone droplet is greater than 0.5 micron, more preferably greater than 1 micron, ideally from 2 to 8 micron.
  • Silicone particle size may be measured by means of a laser light scattering technique, for example using a 2600D Particle Sizer from Malvern Instruments.
  • Suitable pre-formed emulsions include Xiameter MEM 1785 and microemulsion DC2-1865 available from Dow Corning. These are emulsions
  • Cross-linked silicone gums are also available in a pre-emulsified form, which is advantageous for ease of formulation.
  • a further preferred class of silicones for inclusion in shampoos and conditioners of the invention are amino functional silicones.
  • amino functional silicone is meant a silicone containing at least one primary, secondary or tertiary amine group, or a quaternary ammonium group.
  • suitable amino functional silicones include: polysiloxanes having the CTFA designation "amodimethicone”.
  • Specific examples of amino functional silicones suitable for use in the invention are the aminosilicone oils DC2-8220, DC2-8166 and DC2-8566 (all ex Dow Corning).
  • Suitable quaternary silicone polymers are described in EP-A-0 530 974.
  • a preferred quaternary silicone polymer is K3474, ex Goldschmidt.
  • emulsions of amino functional silicone oils with non ionic and/or cationic surfactant are also suitable from suppliers of silicone oils such as Dow Corning and General Electric. Specific examples include DC939 Cationic Emulsion and the non-ionic emulsions DC2- 7224, DC2-8467, DC2-8177 and DC2-8154 (all ex Dow Corning).
  • Non-Silicone Oils are also available from suppliers of silicone oils such as Dow Corning and General Electric. Specific examples include DC939 Cationic Emulsion and the non-ionic emulsions DC2- 7224, DC2-8467, DC2-8177 and DC2-8154 (all ex Dow Corning).
  • the total amount of silicone is preferably from 0.01 wt% to 10 %wt of the total composition more preferably from 0.1 wt% to 5 wt%, most preferably 0.5 wt% to 3 wt% is a suitable level.
  • compositions according to the present invention may also comprise a dispersed, non-volatile, water-insoluble oily conditioning agent.
  • a dispersed, non-volatile, water-insoluble oily conditioning agent Preferably such non-silicone conditioning oily conditioning agents are present in conditioner compositions.
  • insoluble is meant that the material is not soluble in water (distilled or equivalent) at a concentration of 0.1 % (w/w), at 25°C.
  • Suitable oily or fatty materials are selected from hydrocarbon oils, fatty esters and mixtures thereof.
  • Straight chain hydrocarbon oils will preferably contain from about 12 to about 30 carbon atoms.
  • polymeric hydrocarbons of alkenyl monomers such as C2-C6 alkenyl monomers.
  • hydrocarbon oils include paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, and mixtures thereof.
  • Branched-chain isomers of these compounds, as well as of higher chain length hydrocarbons, can also be used.
  • Suitable fatty esters are characterised by having at least 10 carbon atoms, and include esters with hydrocarbyl chains derived from fatty acids or alcohols, Monocarboxylic acid esters include esters of alcohols and/or acids of the formula R'COOR in which R' and R independently denote alkyl or alkenyl radicals and the sum of carbon atoms in R' and R is at least 10, preferably at least 20. Di- and trialkyl and alkenyl esters of carboxylic acids can also be used.
  • Particularly preferred fatty esters are mono-, di- and triglycerides, more
  • Preferred materials include cocoa butter, palm stearin, sunflower oil, soyabean oil and coconut oil.
  • the oily or fatty material is suitably present at a level of from 0.05 wt% to 10 wt%, preferably from 0.2 wt% to 5 wt%, more preferably from about 0.5 wt% to 3 wt%.
  • Such compositions will typically comprise one or more conditioning surfactants which are cosmetically acceptable and suitable for topical application to the hair.
  • compositions of the invention will typically also incorporate a fatty alcohol.
  • fatty alcohols 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 22.
  • Fatty alcohols are typically compounds containing straight chain alkyl groups. Examples of suitable fatty alcohols include cetyl alcohol, stearyl alcohol and mixtures thereof. The use of these materials is also
  • compositions of the invention are advantageous in that they contribute to the overall conditioning properties of compositions of the invention.
  • the level of fatty alcohol in conditioners of the invention will generally range from 0.01 to 10%, preferably from 0.1 % to 8%, more preferably from 0.2 % to 7 %, most preferably from 0.3 % to 6 % by weight of the composition.
  • the weight ratio of cationic surfactant to fatty alcohol is suitably from 1 : 1 to 1 : 10, preferably from 1 : 1 .5 to 1 :8, optimally from 1 :2 to 1 :5.
  • Cationic polymers may be present in the formulation.
  • Suitable cationic polymers may be homopolymers which are cationically substituted or may be formed from two or more types of monomers.
  • the weight average (M w ) molecular weight of the polymers will generally be between 100 000 and 2 million daltons.
  • the polymers will have cationic nitrogen containing groups such as quaternary ammonium or protonated amino groups, or a mixture thereof. If the molecular weight of the polymer is too low, then the conditioning effect is poor. If too high, then there may be problems of high extensional viscosity leading to stringiness of the composition when it is poured.
  • the cationic nitrogen-containing group will generally be present as a substituent on a fraction of the total monomer units of the cationic polymer.
  • the polymer when it is not a homopolymer it can contain spacer non-cationic monomer units.
  • spacer non-cationic monomer units Such polymers are described in the CTFA Cosmetic Ingredient Directory, 3rd edition.
  • the ratio of the cationic to non-cationic monomer units is selected to give polymers having a cationic charge density in the required range, which is generally from 0.2 to 3.0 meq/gm.
  • the cationic charge density of the polymer is suitably determined via the Kjeldahl method as described in the US
  • Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as (meth)acrylamide, alkyi and dialkyi (meth)acrylamides, alkyi (meth)acrylate, vinyl caprolactone and vinyl pyrrolidine.
  • the alkyi and dialkyi substituted monomers preferably have C1 -C7 alkyi groups, more preferably C1 -3 alkyi groups.
  • Other suitable spacers include vinyl esters, vinyl alcohol, 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, are preferred.
  • Amine substituted vinyl monomers and amines can be polymerized in the amine form and then converted to ammonium by quaternization.
  • the cationic polymers can comprise mixtures of monomer units derived from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers.
  • Suitable cationic polymers include, for example: cationic diallyl quaternary ammonium-containing polymers including, for example, dimethyldiallylammonium chloride homopolymer and copolymers of acrylamide and dimethyldiallylammonium chloride, referred to in the industry (CTFA) as Polyquaternium 6 and Polyquaternium 7, respectively; 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); cationic polyacrylamides(as described in W095/2231 1 ).
  • cationic polymers that can be used include cationic polysaccharide polymers, such as cationic cellulose derivatives, cationic starch derivatives, and cationic guar gum derivatives.
  • Cationic polysaccharide polymers suitable for use in compositions of the invention include monomers of the formula: A-O-[R-N + (R 1 )(R 2 )(R 3 )X " ], wherein: 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 represent alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each group containing up to about 18 carbon atoms.
  • the total number of carbon atoms for each cationic moiety is preferably about 20 or less, and X is an anionic counterion.
  • 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 Polyquaternium 24. These materials are available from the Amerchol Corporation, for instance under the tradename Polymer LM-200.
  • Suitable cationic polysaccharide polymers include quaternary nitrogen- containing cellulose ethers (e.g. as described in U.S. Patent 3,962,418), and copolymers of etherified cellulose and starch (e.g. as described in U.S. Patent 3,958,581 ).
  • a particularly suitable type of cationic polysaccharide polymer that can be used is a cationic guar gum derivative, such as guar hydroxypropyltrimethylammonium chloride (commercially available from Rhodia in their JAGUAR trademark series).
  • a cationic guar gum derivative such as guar hydroxypropyltrimethylammonium chloride (commercially available from Rhodia in their JAGUAR trademark series).
  • examples of such materials are JAGUAR C13S, JAGUAR C14, JAGUAR C15, JAGUAR C17 and JAGUAR C16 Jaguar CHT and JAGUAR C162.
  • Mixtures of any of the above cationic polymers may be used.
  • Cationic polymer will generally be present in the composition of the invention at levels of from 0.01 to 5%, preferably from 0.05 to 1 %, more preferably from 0.08 to 0.5% by total weight of cationic polymer based on the total weight of the composition.
  • Other Optional Ingredients are preferably from 0.01 to 5%, preferably from 0.05 to 1 %, more preferably from 0.08 to 0.5% by total weight of cationic polymer based on the total weight of the composition.
  • a composition of the invention may contain from 0.01 to 2 wt% of the total composition of other ingredients for enhancing performance and/or consumer acceptability.
  • Such ingredients include fragrance, dyes and pigments, pH adjusting agents, pearlescers or opacifiers, viscosity modifiers, preservatives, and natural hair nutrients such as botanicals, fruit extracts, sugar derivatives and amino acids.
  • the composition is a rinse off hair treatment composition.
  • a rinse off composition is applied hair preferably wet hair, and left on the hair for up to I hour, preferably left on the hair for up to 30 minutes before it is removed by rinsing.
  • the dye-polymers is preferably mixed with analagous dye-polymer made with reactive red or reactive yellow dyes.
  • the reactive red or reactive yellow dyes are mono-azo or bis-azo compounds.
  • the reactive red and yellow dyes may be attached to the same polymer backbone as the bis-azo reactive dye.
  • a means one or more.
  • the wt% dye on polymer was calculated from the UV-VIS absorption of the dye- polymer, using an extinction coefficient of 50 000 L mol "1 cm “1 for the dye.
  • a 1 .4g human bleached blond hair truss was placed in a 1 .4g aqueous solution of the dye polymer and agitated for 60 seconds.
  • the aqueous solution contained 1 .4wt% of the dye-polymer.
  • the truss was removed, rinsed in demineralised water for 60 seconds, dried and the colour measured using a reflectometer and expressed as the CIE L * a * b * values.
  • Plantacare 818 UP Coco Glucoside 7

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Abstract

Composition colorante pour cheveux comprenant un colorant polymère, le colorant polymère étant constitué d'un polymère à charge positive lié par covalence à un colorant réactif à charge négative, le colorant réactif étant un colorant bisazoïque de structure (I) où le cycle A est substitué par au moins un groupe réactif hétérocyclique et/ou un groupe sulfonate.
PCT/EP2012/051256 2011-03-10 2012-01-26 Composition WO2012119810A2 (fr)

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EP12708737.7A EP2683353A2 (fr) 2011-03-10 2012-01-26 Composition
BR112013022596A BR112013022596A2 (pt) 2011-03-10 2012-01-26 composição para tingir cabelo, método para coloração de cabelo e uso de um corante polimérico para coloração de cabelo
CN2012800124516A CN103415279A (zh) 2011-03-10 2012-01-26 组合物

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014111280A1 (fr) * 2013-01-15 2014-07-24 Unilever Plc Composition
WO2014111281A1 (fr) * 2013-01-15 2014-07-24 Unilever Plc Composition
US9949542B2 (en) 2014-10-29 2018-04-24 Noxell Corporation Hair colouration, method and kit thereof
US9949543B2 (en) 2014-10-29 2018-04-24 Noxell Corporation Hair colouration, method and kit thereof
US9980892B2 (en) 2014-04-14 2018-05-29 Conopce, Inc. Skin care composition
US10689801B2 (en) 2014-04-22 2020-06-23 Millikan & Company Colored coatings and artificial leathers containing colorant complexes
WO2020127542A1 (fr) * 2018-12-19 2020-06-25 Unilever Plc Système de dépôt pour cheveux

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US4182612A (en) 1977-01-31 1980-01-08 The Gillette Company Method for dyeing human hair with cationic polymeric dyes
FR2456764A2 (fr) 1979-05-18 1980-12-12 Oreal Nouveaux polymeres colorants, leur preparation et leur utilisation
EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
WO1995022311A1 (fr) 1994-02-18 1995-08-24 Unilever Plc Compositions de detersif pour soins corporels
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WO2009090121A1 (fr) 2008-01-17 2009-07-23 Basf Se Colorants capillaires polymères
WO2009090125A1 (fr) 2008-01-17 2009-07-23 Basf Se Colorants capillaires polymères
WO2011113680A2 (fr) 2010-03-19 2011-09-22 Unilever Plc Composition

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EP0501252B1 (fr) * 1991-02-27 1996-04-10 Bayer Ag Colorants réactifs bifonctionnels
FR2882929B1 (fr) * 2005-03-14 2008-02-22 Oreal Procede de coloration des cheveux a partir d'un polymere colore anionique
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US3958581A (en) 1972-05-17 1976-05-25 L'oreal Cosmetic composition containing a cationic polymer and divalent metal salt for strengthening the hair
US3962418A (en) 1972-12-11 1976-06-08 The Procter & Gamble Company Mild thickened shampoo compositions with conditioning properties
US4009256A (en) 1973-11-19 1977-02-22 National Starch And Chemical Corporation Novel shampoo composition containing a water-soluble cationic polymer
US4182612A (en) 1977-01-31 1980-01-08 The Gillette Company Method for dyeing human hair with cationic polymeric dyes
FR2456764A2 (fr) 1979-05-18 1980-12-12 Oreal Nouveaux polymeres colorants, leur preparation et leur utilisation
EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
WO1995022311A1 (fr) 1994-02-18 1995-08-24 Unilever Plc Compositions de detersif pour soins corporels
WO1996031188A1 (fr) 1995-04-06 1996-10-10 Unilever Plc Compositions pour traitement capillaire
WO2008009579A1 (fr) 2006-07-18 2008-01-24 Ciba Holding Inc. Colorants polymères pour cheveux
WO2009090121A1 (fr) 2008-01-17 2009-07-23 Basf Se Colorants capillaires polymères
WO2009090125A1 (fr) 2008-01-17 2009-07-23 Basf Se Colorants capillaires polymères
WO2011113680A2 (fr) 2010-03-19 2011-09-22 Unilever Plc Composition

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014111280A1 (fr) * 2013-01-15 2014-07-24 Unilever Plc Composition
WO2014111281A1 (fr) * 2013-01-15 2014-07-24 Unilever Plc Composition
US9980892B2 (en) 2014-04-14 2018-05-29 Conopce, Inc. Skin care composition
US10689801B2 (en) 2014-04-22 2020-06-23 Millikan & Company Colored coatings and artificial leathers containing colorant complexes
US9949542B2 (en) 2014-10-29 2018-04-24 Noxell Corporation Hair colouration, method and kit thereof
US9949543B2 (en) 2014-10-29 2018-04-24 Noxell Corporation Hair colouration, method and kit thereof
US10681971B2 (en) 2014-10-29 2020-06-16 Noxell Corporation Hair colouration, method and kit thereof
US10687594B2 (en) 2014-10-29 2020-06-23 Noxell Corporation Hair colouration, method and kit thereof
WO2020127542A1 (fr) * 2018-12-19 2020-06-25 Unilever Plc Système de dépôt pour cheveux
US20220023178A1 (en) * 2018-12-19 2022-01-27 Conopco, Inc., D/B/A Unilever Deposition system for hair

Also Published As

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CN103415279A (zh) 2013-11-27
WO2012119810A3 (fr) 2013-08-22
BR112013022596A2 (pt) 2016-08-09
EP2683353A2 (fr) 2014-01-15

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