WO2011113249A1 - Method of treating hair - Google Patents
Method of treating hair Download PDFInfo
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- WO2011113249A1 WO2011113249A1 PCT/CN2010/075833 CN2010075833W WO2011113249A1 WO 2011113249 A1 WO2011113249 A1 WO 2011113249A1 CN 2010075833 W CN2010075833 W CN 2010075833W WO 2011113249 A1 WO2011113249 A1 WO 2011113249A1
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- Prior art keywords
- dye
- blue
- acid
- polymer
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- IXFLTQIVXGGLDV-UHFFFAOYSA-N CN(C(CC1Cc(c(F)c(c(F)c2F)F)c2[I]=C)O)C1O Chemical compound CN(C(CC1Cc(c(F)c(c(F)c2F)F)c2[I]=C)O)C1O IXFLTQIVXGGLDV-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N Cc(cc1)ccc1[N+]([O-])=O Chemical compound Cc(cc1)ccc1[N+]([O-])=O ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- 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 method for dying the hair.
- Numerous cationic polymeric dyes have been disclosed for use as a colorant for human hair, for example in US 4,228,259; US 4,182,612 or FR 2 456 764, WO2008/009579 and WO2009/090121 to WO2009/090125.
- the present invention relates to a method for colouring hair, comprising the step of applying to the hair a composition comprising a dye polymer in which the dye polymer is obtained more preferably obtained by the reaction of i)a NH 2 group directly and covalently bound to an aromatic ring of a dye with ii)a reactive group of a polymeric compound; in which the reactive group is selected from the group consisting of isocyanate; oxazolone; epoxide; ester, and anhydride.
- the dye-polymer for use with the method of the invention is formed by the step of reaction a reactive polymer with the NH 2 group of a dye, the NH 2 group being directly covalently bound to an aromatic ring of the dye.
- the reactive polymer has a group for reacting with the NH 2 , the group selected from: isocyanate; oxazolone; epoxide; ester, and anhydride, preferably epoxide or anhydride, most preferably anhydride.
- ester classes activated esters are preferred.
- R is H, alkyl, aryl or selected so that the COOR group forms an anhydride.
- R groups examples include Z is a polymer.
- reaction is of the form:
- Non-limiting examples of polymers formed by such reactions are:
- Catalysts may be used to accelerate the reactions.
- Non-limiting examples of polymers formed by such reactions are:
- the dye must contain an NH 2 group covIERly bound to an aromatic ring of the dye.
- the NH 2 is covIERly bound to an aromatic ring of the dye, wherein the aromatic ring is in conjugation with the chromophore of the dye.
- the dye preferably contains the moiety within the aromatic ring structure of the dye.
- Preferred dyes include:
- the dye does not contain reactive groups or polymerisable double bonds.
- a dye containing a reactive groups is made up of a chromophore which is (inked to a reactive group that undergoes addition or substitution reactions with - OH, -SH and -NH 2 groups to form covalent bonds.
- Reactive dyes are described in Industrial Dyes (K.Hunger ed, Wiley VCH 2003). Many Reactive dyes are listed in the colour index (Society of Dyers and Colourists and American Association of Textile Chemists and Colorists).
- Reactive groups are, for example, dichlorotriazinyl, difluorochloropyrimidine, monofluorotrazinyl, dichloroquinoxaline, vinylsulfone, difluorotriazine, monochlorotriazinyl, bromoacrlyamide and trichloropyrimidine.
- Dyes are organic molecules that have an absorption coefficient of greater than 4000, preferably greater than 10 000 mol " L cm "1 at any wavelength in the range 400-700nm. Molar absorption coefficients are preferably measured in an organic solvent, preferably propan-2-ol, using a 1 , 5 or 10 cm cell.
- the dye is preferably selected from organic dyes selected from the following chromophore classes: Aminoketone, anthraquinone, azo, oxazine, azine, triphenodioxazine, triphenyl methane, naphthalimide, xanthene and phthalocyanin, more preferably azo, anthraquinone, naphthalimide and azine chromophore classes, most preferably azo and anthraquinone.
- the dye of preference is an anthraquinone.
- the dye may be cationic, anionically, or uncharged. Examples of uncharged dyes are found in the disperse dye category. Examples of anionic charged dyes are found in the acid and direct dye category. Examples of cationic charged dyes are found in the basic dye category.
- the dye is preferably uncharged or has an anionic charge. Most preferably the dye is an anionic charged dye.
- Preferred dyes containing -NH 2 groups covalently bound to an aromatic ring of the dye are: acid violet 1 ; acid violet 3; acid violet 6; acid violet 11 ; acid violet 13; acid violet 14; acid violet 19; acid violet 20; acid violet 36; acid violet 36:1 ; acid violet 41 ; acid violet 42; acid violet 43; acid violet 50; acid violet 51 ; acid violet 63; acid violet 48; acid blue 25; acid blue 40; acid blue 40:1 ; acid blue 41 ; acid blue 45; acid blue 47; acid blue 49; acid blue 51 ; acid blue 53; acid blue 56; acid blue 61 ; acid blue 61 :1 ; acid blue 62; acid blue 69; acid blue 78; acid blue 81 :1 ; acid blue 92; acid blue 96; acid blue 108; acid blue 111 ; acid blue 215; acid blue 230; acid blue 277; acid blue 344; acid blue 117; acid blue 124; acid blue 129; acid blue 129:1 ; acid blue 138;
- Further preferred dyes are selected from mono-azo dyes which contain a phenyl group directly attached to the azo group, wherein the phenyl group has an NH 2 groups covalent bound to it.
- the reactive polymer may be synthesised by polymerisation of the monomers, preferably the monomers are alkenes.
- the monomers are alkenes.
- 2-80 mol%, more preferably 5- 55 mol%. of the monomer are selected from monomers which contain or form isocyanate; oxazolone; epoxide; ester, or anhydride groups on polymerisation.
- Preferred Suitable monomers include maleic anhydride, glycidyl acrylate, 2- glycidyl methacrylate, 2-vinyl-4,4-dimethyl-5-oxazolone, vinyl isocyanate, 2- Isocyanatoethyl methacrylate, N-methacryloxysuccinimide,.
- the reactive polymer may comprise a co-monomer.
- Preferred co-monomers may be selected from alkenes, acrylates and styrenes. Suitable co-monomers include diethylaminoethylmethacrylate, dimethylaminopropyl metacryamide, methyl vinylether, methacrylic acid, 2-acry]amido-2-methyl-1-propanesulfonic acid, 2- hydroxyethyl acrylate; 2-hydroxyethyl methacrylate dimethylaminoethyl methacrylate, methyl methacrylate, methyl acrylate, hydroxyethyl methacryiate, ethyl methacrylate, ethyl acrylate, hydroxyethyl acrylate, butyl methacrylate, butyl acrylate, acrylamide, t-butyl methacrylate, t-butyl acrylate, sodium 4- vinylbenzenesulphonate,
- the monomers within the polymer may be arranged in any suitable manner. For example as alternating copolymers possess regularly alternating monomer residues; Periodic copolymers have monomer residue types arranged in a repeating sequence; Random copolymers have a random sequence of monomer residue types; Statistical copolymers have monomer residues arranged according to a known statistical rule; Block copolymers have two or more homopolymer subunits linked by covalent bonds. Most preferably the polymer is a random copolymer.
- the polymer preferably has a molecular weight of 2000 and greater. Preferred ranges are from 2000 to 1 000 000, more preferred ranges are from 5000 to 100 000. In this context the molecular weight is the number average molecular weight.
- the polymeric compound can comprise a siloxane polymers with pendant isocyanate; oxazolone; epoxide; ester, or anhydride groups.
- the polymeric compound within the dye polymer is cova!ently bound to 1 to 100 dye molecules. More preferably 1 to 40 dye molecules. Most preferably 1 to 10 dye molecules.
- the polymer may contain cationic and anionic charged groups.
- the dye is preferably uncharged or anionic charged.
- the polymer does not contain a primary amine.
- the dye is preferably uncharged or has an anionic charge. Most preferably the dye is anionic charged.
- Anionic dyes are particularly preferred when the polymer carries anionic groups on the co-monomers. Particularly preferred is a dye polymer having a poly (methyl vinyl ether-alt-maleic anhydride) polymer reacted with an anionic dye.
- Combination of polymeric dyes may be used to achieve a wide colour palette
- a palette of three or more polymeric dyes is preferable, particularly preferred is a palette of three polymeric dyes. It is most effective to use dye-polymer mixtures containing a red dye-polymer, a yellow dye-polymer and a blue dye polymer. Variation of the fractions of blue, yellow, and red in the mixture enables many colours to be reached, for example black, and brown.
- Poly (methyl vinyl ether-alt-maleic anhydride) polymers reacted with an anionic dye are most preferred.
- the anionic dye contains 1 or 2 sulphonate groups, most preferably 1.
- the level of polymeric dye within the composition is preferably from 0.001 to 5wt% of the total composition, more preferably from 0.01 to 1wt% most preferably from 0.04 to 0.4wt%.
- the method of the invention comprises a rinse-off step.
- the composition is a shampoo, conditioner or hair dye composition.
- the composition is a shampoo it preferably comprises from 5 to 50wt% of the total composition of a cleansing surfactant.
- the cleansing surfactant comprises anionic and amphoteric surfactant.
- the composition is a conditioning composition it preferably comprises a conditioning active such as fatty alcohols, fatty acids, fatty amides and fatty esters, silicones, cationic surfactants etc.
- the composition contains a perfume.
- the perfume is present at 0.001 to 5wt% of the total composition.
- the composition of the invention has a pH of from 3 to 9, preferably from 4 to 8.
- the composition contains greater than 40wt% of the total composition of water.
- the composition is a liquid and the viscosity of the liquid is greater than 4 centipoise at 293K. Viscosity was measured using a falling ball viscometer, with Stokes' law used to calculate the viscosity of the fluid.
- a 0.04 wt% solution of the dye polymers was made in demineralised water.
- the colour of the hair was assessed by measuring the reflectance of the swatch using a reflectomer and expressing the colour as CIE L*a*b* values and as a ⁇ value relative to an undyed control. The swatch was then rinsed in water for 60 seconds under a running tap, dried and the colour remeasured.
Abstract
A method for colouring hair, comprising the step of applying to the hair a composition comprising a dye polymer in which the dye polymer is obtainable by the reaction of a NH2 group directly and covalently bound to an aromatic ring of a dye i) with a reactive group of a polymeric compound ii) in which the reactive group is selected from the group consisting of isocyanate; oxazolone; epoxide; ester, and anhydride.
Description
METHOD OF TREATING HAIR
The present invention relates to a method for dying the hair. Numerous cationic polymeric dyes have been disclosed for use as a colorant for human hair, for example in US 4,228,259; US 4,182,612 or FR 2 456 764, WO2008/009579 and WO2009/090121 to WO2009/090125.
Zollinger in Color Chemistry (Wiley-VCH 2003) discloses that several million different coloured compounds have been synthesized. A large number of dyes contain NH2 groups covalently bound to an aromatic ring of the dye.
However there remains the need for dyes containing NH2 groups covalently bound to an aromatic ring of the dye to be liked to polymers. Such polymeric dyes can be used to colour the hair.
Description of the invention
The present invention relates to a method for colouring hair, comprising the step of applying to the hair a composition comprising a dye polymer in which the dye polymer is obtained more preferably obtained by the reaction of i)a NH2 group directly and covalently bound to an aromatic ring of a dye with ii)a reactive group of a polymeric compound; in which the reactive group is selected from the group consisting of isocyanate; oxazolone; epoxide; ester, and anhydride.
Detailed Description of the Invention
REACTION DESCRIPTION The dye-polymer for use with the method of the invention is formed by the step of reaction a reactive polymer with the NH2 group of a dye, the NH2 group being directly covalently bound to an aromatic ring of the dye. The reactive polymer has a group for reacting with the NH2, the group selected from: isocyanate; oxazolone;
epoxide; ester, and anhydride, preferably epoxide or anhydride, most preferably anhydride. Of the ester classes, activated esters are preferred.
Suitable post-polymerization modifications of reactive polymers for use with the invention are described in detail in Gauthier, MA, Gibson, M.I., and Klok H-A., Angew. Chem. Int. Ed 2009 48, 48058,
Preferably the reactions are selected from: Reaction (a): ester and anhydrides
Where R is H, alkyl, aryl or selected so that the COOR group forms an anhydride.
Most preferably the reaction is of the form:
Such reactions are discussed in Macromolecules 1994, 27, 7121-7126.
Non-limiting Examples of polymers formed by such reactions are:
Reaction (c): oxazolone and isocynate
Reaction with oxazolone and isocynate are exemplified below
Dye description
Examples of dyes are described in Industrial Dyes (K.Hunger ed, Wiley VCH 2003 and in the colour index (Society of Dyers and Colourists and American Association of Textile Chemists and Colorists).
The dye must contain an NH2 group covaiently bound to an aromatic ring of the dye. Preferably the NH2 is covaiently bound to an aromatic ring of the dye, wherein the aromatic ring is in conjugation with the chromophore of the dye.
The dye preferably contains the moiety
within the aromatic ring structure of the dye. Preferred dyes include:
Preferably the dye does not contain reactive groups or polymerisable double bonds. A dye containing a reactive groups is made up of a chromophore which is (inked to a reactive group that undergoes addition or substitution reactions with - OH, -SH and -NH2 groups to form covalent bonds. Reactive dyes are described in Industrial Dyes (K.Hunger ed, Wiley VCH 2003). Many Reactive dyes are listed in the colour index (Society of Dyers and Colourists and American Association of Textile Chemists and Colorists). Reactive groups are, for example, dichlorotriazinyl, difluorochloropyrimidine, monofluorotrazinyl, dichloroquinoxaline, vinylsulfone, difluorotriazine, monochlorotriazinyl, bromoacrlyamide and trichloropyrimidine. Dyes are organic molecules that have an absorption coefficient of greater than 4000, preferably greater than 10 000 mol" L cm"1 at any wavelength in the range 400-700nm. Molar absorption coefficients are preferably measured in an organic solvent, preferably propan-2-ol, using a 1 , 5 or 10 cm cell. The dye is preferably selected from organic dyes selected from the following chromophore classes: Aminoketone, anthraquinone, azo, oxazine, azine, triphenodioxazine, triphenyl methane, naphthalimide, xanthene and phthalocyanin, more preferably azo, anthraquinone, naphthalimide and azine chromophore classes, most preferably azo and anthraquinone. The dye of preference is an anthraquinone.
The dye may be cationic, anionically, or uncharged. Examples of uncharged dyes are found in the disperse dye category. Examples of anionic charged dyes are found in the acid and direct dye category. Examples of cationic charged dyes are
found in the basic dye category. The dye is preferably uncharged or has an anionic charge. Most preferably the dye is an anionic charged dye.
Preferred dyes containing -NH2 groups covalently bound to an aromatic ring of the dye, are: acid violet 1 ; acid violet 3; acid violet 6; acid violet 11 ; acid violet 13; acid violet 14; acid violet 19; acid violet 20; acid violet 36; acid violet 36:1 ; acid violet 41 ; acid violet 42; acid violet 43; acid violet 50; acid violet 51 ; acid violet 63; acid violet 48; acid blue 25; acid blue 40; acid blue 40:1 ; acid blue 41 ; acid blue 45; acid blue 47; acid blue 49; acid blue 51 ; acid blue 53; acid blue 56; acid blue 61 ; acid blue 61 :1 ; acid blue 62; acid blue 69; acid blue 78; acid blue 81 :1 ; acid blue 92; acid blue 96; acid blue 108; acid blue 111 ; acid blue 215; acid blue 230; acid blue 277; acid blue 344; acid blue 117; acid blue 124; acid blue 129; acid blue 129:1 ; acid blue 138; acid blue 145; direct violet 99; direct violet 5; direct violet 72; direct violet 16; direct violet 78; direct violet 77; direct violet 83; food black 2; direct blue 33; direct blue 41 ; direct blue 22; direct blue 71 ; direct blue 72; direct blue 74; direct blue 75; direct blue 82; direct blue 96; direct blue 10; direct blue 111 ; direct blue 120; direct blue 120:1 ; direct blue 121 ; direct blue 122; direct blue 123; direct blue 124; direct blue 126; direct blue 127; direct blue 128; direct blue 129; direct blue 130; direct blue 132; direct blue 133; direct blue 35; direct blue 138; direct blue 140; direct blue 145; direct blue 148; direct blue 149; direct blue 159; direct blue 162; direct blue 163; food black 2; food black 1 wherein the acid amide group is replaced by NH2; Basic Violet 2; Basic Violet 5; Basic Violet 12; Basic Violet 14; Basic Violet 8; Basic Blue 12; Basic Blue 16; Basic Blue 17; Basic Blue 47; Basic Blue 99; disperse blue 1 ; disperse blue 5; disperse blue 6; disperse blue 9; disperse blue 11 ; disperse blue 19; disperse blue 20; disperse blue 28; disperse blue 40; disperse blue 56; disperse blue 60; disperse blue 81 ; disperse blue 83; disperse blue 87; disperse blue 104; disperse blue 118; disperse violet 1 ; disperse violet 4, disperse violet 8, disperse violet 17, disperse violet 26; disperse violet 28; solvent violet 26; solvent blue 12; solvent blue 13; solvent blue 18; solvent blue 68; solvent blue 76; disperse red 4; disperse red 11 ; disperse red 15; disperse red 31; disperse red 53; disperse red 55; disperse red 60; disperse red 63; disperse red 86; disperse red 91 ; disperse red 92; basic red 2; basic red 3; basic red 4; basic red 5; basic red 6; basic red 9;
basic red 30; disperse yellow 9; disperse yellow 11 ; basic yellow 5; basic yellow 6; basic yellow 7; basic yellow 9; basic brown 1 ; basic brown 2; basic brown 4; basic brown 5; basic brown 17; disperse orange 3; disperse orange 3:1 ; disperse orange 6; disperse orange 11; disperse green 2; acid red 33; acid red 30; acid red 34; acid yellow 7; acid yellow 9; acid yellow 66; acid green 20; acid green 33; acid brown 4; acid brown 9; disperse black 9; disperse black 3 disperse black 4; disperse black 7 and acid black 1.
Further preferred dyes are selected from mono-azo dyes which contain a phenyl group directly attached to the azo group, wherein the phenyl group has an NH2 groups covalent bound to it.
REACTIVE POLYMER DESCRIPTION The reactive polymer may be synthesised by polymerisation of the monomers, preferably the monomers are alkenes. Preferably 2-80 mol%, more preferably 5- 55 mol%. of the monomer are selected from monomers which contain or form isocyanate; oxazolone; epoxide; ester, or anhydride groups on polymerisation. Preferred Suitable monomers include maleic anhydride, glycidyl acrylate, 2- glycidyl methacrylate, 2-vinyl-4,4-dimethyl-5-oxazolone, vinyl isocyanate, 2- Isocyanatoethyl methacrylate, N-methacryloxysuccinimide,.
The reactive polymer may comprise a co-monomer. Preferred co-monomers may be selected from alkenes, acrylates and styrenes. Suitable co-monomers include diethylaminoethylmethacrylate, dimethylaminopropyl metacryamide, methyl vinylether, methacrylic acid, 2-acry]amido-2-methyl-1-propanesulfonic acid, 2- hydroxyethyl acrylate; 2-hydroxyethyl methacrylate dimethylaminoethyl methacrylate, methyl methacrylate, methyl acrylate, hydroxyethyl methacryiate, ethyl methacrylate, ethyl acrylate, hydroxyethyl acrylate, butyl methacrylate, butyl acrylate, acrylamide, t-butyl methacrylate, t-butyl acrylate, sodium 4- vinylbenzenesulphonate, styrene, benyl methacrylate, acrylic acid, vinyl acetate, vinyl pyridine, sodium acrylate, diethylaminoethyl methacrylate (preferred), 4- vinylphenol, methacrylic acid, acrylonitrile, 4-vinyl-9H-carbazole, sodium
methacrylate, 4,4-dimethyl-2-vinyloxazol-5(4H)-one, 4,4-dimethyl-2-(prop-1-en-2- yl)oxazol-5(4H)-one, vinyl pyrrolidone, 4-pentenoic acid, ethyl 2-cyanoacrylate, stearyl acrylate, glycosyloxyethyl methacryrlate, methyl ether methacrylate, poly(ethylene glycol) ethyl ether methacrylate, poly(ethylene glycol) methyl ether methacrylate, isopropyl methacrylate, 2-hydroxypropyl methacrylate, 2- isocyanatoethyl methacrylate, 2-(methylthio)ethyl methacrylate, 2-aminoethyl methacrylate hydrochloride (preferred), furfuryl methacrylate, cyclohexyl methacrylate, 2,2,2-trifluoroethyl methacrylate, tetrahydrofurfuryl methacrylate, hexyl methacrylate, 3-chloro-2-hydroxypropyl methacrylate, N-isopropylacrylamide, Ν,Ν-dimethylacrlyamide, 2-ethylhexyl methacrylate, 2-(dimethylamino)ethyl methacrylamide, potassium 3-sulphopropyl methacrylate , potassium 5-methyl-4- oxohex-5-ene-1-sulphonate, 2-butoxyethyl methacrylate, 2-(t-butylamino)ethyl methacrylate, 2-acrlamido-2-methyl-1-propanesulphonic acid, 4-vinylbenzoic acid, N-(6-aminopyridin-2-yl)acrylamide, N-(3-aminophenyl) acrylamide, 2-acrylamido pyridine, 4-vinylphenylboronic acid, itaconic acid, 2-aminoethyl methacrylate, and methylvinyl ether.
The monomers within the polymer may be arranged in any suitable manner. For example as alternating copolymers possess regularly alternating monomer residues; Periodic copolymers have monomer residue types arranged in a repeating sequence; Random copolymers have a random sequence of monomer residue types; Statistical copolymers have monomer residues arranged according to a known statistical rule; Block copolymers have two or more homopolymer subunits linked by covalent bonds. Most preferably the polymer is a random copolymer. The polymer preferably has a molecular weight of 2000 and greater. Preferred ranges are from 2000 to 1 000 000, more preferred ranges are from 5000 to 100 000. In this context the molecular weight is the number average molecular weight. This is the ordinary arithmetic mean of the molecular weights of the individual macromolecules. It is determined by measuring the molecular weight of j polymer molecules, summing the weights, and dividing by Molecular weights are determined by Gel Permeations Chromatography.
In a further embodiment the polymeric compound can comprise a siloxane polymers with pendant isocyanate; oxazolone; epoxide; ester, or anhydride groups. DYE POLYMER DESCRIPTION
Preferably the polymeric compound within the dye polymer is cova!ently bound to 1 to 100 dye molecules. More preferably 1 to 40 dye molecules. Most preferably 1 to 10 dye molecules.
Apart from the charge on the dye, the polymer may contain cationic and anionic charged groups.
For polymers which carry cationic groups on the co-monomers the dye is preferably uncharged or anionic charged.
Preferably the polymer does not contain a primary amine.
The dye is preferably uncharged or has an anionic charge. Most preferably the dye is anionic charged. Anionic dyes are particularly preferred when the polymer carries anionic groups on the co-monomers. Particularly preferred is a dye polymer having a poly (methyl vinyl ether-alt-maleic anhydride) polymer reacted with an anionic dye.
Combination of polymeric dyes may be used to achieve a wide colour palette For colouration of hair a palette of three or more polymeric dyes is preferable, particularly preferred is a palette of three polymeric dyes. It is most effective to use dye-polymer mixtures containing a red dye-polymer, a yellow dye-polymer and a blue dye polymer. Variation of the fractions of blue, yellow, and red in the mixture enables many colours to be reached, for example black, and brown.
Poly (methyl vinyl ether-alt-maleic anhydride) polymers reacted with an anionic dye are most preferred. Preferably the anionic dye contains 1 or 2 sulphonate groups, most preferably 1.
The level of polymeric dye within the composition is preferably from 0.001 to 5wt% of the total composition, more preferably from 0.01 to 1wt% most preferably from 0.04 to 0.4wt%.
Preferably, the method of the invention comprises a rinse-off step.
Preferably, the composition is a shampoo, conditioner or hair dye composition. Where the composition is a shampoo it preferably comprises from 5 to 50wt% of the total composition of a cleansing surfactant. Preferably, the cleansing surfactant comprises anionic and amphoteric surfactant. Where the composition is a conditioning composition it preferably comprises a conditioning active such as fatty alcohols, fatty acids, fatty amides and fatty esters, silicones, cationic surfactants etc. Preferably the composition contains a perfume. Preferably the perfume is present at 0.001 to 5wt% of the total composition.
Preferably, the composition of the invention has a pH of from 3 to 9, preferably from 4 to 8. Preferably the composition contains greater than 40wt% of the total composition of water.
Preferably the composition is a liquid and the viscosity of the liquid is greater than 4 centipoise at 293K. Viscosity was measured using a falling ball viscometer, with Stokes' law used to calculate the viscosity of the fluid.
The invention is hereby illustrated by the following non-limiting Examples: Examples
Example 1
Reaction Scheme DAQ.
1g of the polymer (PMVEMA, CAS: 9011-16-9, Mn=80000, Mw=210000 ex Aldrich) was mixed with 0.069g acid blue 62 and 0.030 g 1 ,4-Diaminoanthraquinone (DAQ) of the dye in 50ml of tetrahydrofuran and heated at 65°C for 8 hours. The resultant polymer was further washed by CHCI3 for three times to remove the non-reacted dyes and vacuum dried at r.t. over night thereafter. Finally, the resultant polymer containing non-reacted maleic anhydride underwent hydrolyzation treatment producing carboxylic acid groups of moderate acidity. The polymer was coded PL Example 2
The reaction of example 1 was repeated using the anionic charged dye Acid Blue
1g of the polymer was mixed with 0.1g of the dye n 50ml of tetrahydrofuran and heated at 65°C for 8 hours. The resultant dye polymer was precipitate in petroleum ether and dried in a vacuum. The reaction was conducted twice with polymers of initial molecular weights (Mw) of 200,000 and 2,000,000 and the resultant dye polymers coded P2 and P3. Polymers were obtained from ISP (Gantrez™ AN 119 and An169, respectively).
Analagous polymers were created with DAQ and where coded P4 and P5 corresponding to Gantrez™ AN 119 and An169, respectively.
Example 3: Hair Dyeing Performance
A 0.04 wt% solution of the dye polymers was made in demineralised water. A blonde human hair swatch (weight=1.4g) and a YAK hair swatch (weight =1.6g) was place in 7ml of the dye-polymer solution and agitated for 60 seconds, removed and dried. The colour of the hair was assessed by measuring the reflectance of the swatch using a reflectomer and expressing the colour as CIE L*a*b* values and as a ΔΕ value relative to an undyed control. The swatch was then rinsed in water for 60 seconds under a running tap, dried and the colour remeasured. The swatch was then washed in 0.5g/L Sodium lauryl ether sulphate (3 ethoxy group) surfactant solution for 60 seconds, rinsed in demineralised water.dried and remmeasured. The results are summarised below
Claims
What is claimed is: 1. A method for colouring hair, comprising the step of applying to the hair a composition comprising a dye polymer in which the dye polymer is obtainable by the reaction of a H2 group directly and covalently bound to an aromatic ring of a dye i) with a reactive group of a polymeric compound ii) in which the reactive group is selected from the group consisting of isocyanate; oxazolone; epoxide; ester, and anhydride.
2. A method according to claim 1 comprising the step of applying to the hair a composition comprising a dye polymer in which the dye polymer is obtained by the reaction of a NH2 group directly and covalently bound to an aromatic ring of a dye i) with a reactive group of a polymeric compound ii) in which the reactive group is selected from the group consisting of isocyanate; oxazolone; epoxide; ester, and anhydride.
3. A method according to claim 1 or claim 2 in which the reactive group of the polymeric compound ii) is an epoxide or anhydride group.
4. A method according to any preceding claim, in which the reactive group of the polymeric compound ii) is an anhydride group.
5. A method according to any preceding claim in which the dye i) has an anionic charge.
6. A method according to any preceding claim in which the dye polymer is a poly (methyl vinyl ether-alt-maleic anhydride) polymer reacted with an anionic dye.
7. A method according to any preceding claim in which the dye polymer is present in the composition at a level from preferably 0.001 to 5wt% of the total composition.
8. A method according to claim 7 in which the dye polymer is present in an aqueous solution at a level from 0.04 to 0.4wt% of the total composition.
9. A method according to any preceding claim in which the composition comprises a mixture of three or more polymeric dyes.
10. A method according to any preceding claim in which the dye i) is selected from the azo, anthraquinone, naphthalimide or azine chromophore classes.
11. A method according to any claim 10 in which the dye i)is selected from the anthraquinone chromophore class.
12. A method according to any preceding claim in which the polymeric compound ii) within the dye polymer is covalently bound to 1 to 10 dye molecules i).
13. A method according to any preceding claim in which the method further comprises rinsing the hair after application of the composition comprising dye.
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2011229417A AU2011229417A1 (en) | 2010-03-19 | 2011-02-24 | Method of treating hair |
PCT/EP2011/052735 WO2011113676A2 (en) | 2010-03-19 | 2011-02-24 | Method of treating hair |
BR112012023598A BR112012023598A2 (en) | 2010-03-19 | 2011-02-24 | hair coloring method |
EA201290934A EA201290934A1 (en) | 2010-03-19 | 2011-02-24 | METHOD OF HAIR TREATMENT |
CN2011800148677A CN102844020A (en) | 2010-03-19 | 2011-02-24 | Method of treating hair |
JP2012557467A JP2013522256A (en) | 2010-03-19 | 2011-02-24 | How to treat hair |
EP11705872A EP2547321A2 (en) | 2010-03-19 | 2011-02-24 | Method of treating hair |
TW100107215A TW201138892A (en) | 2010-03-19 | 2011-03-03 | Method of treating hair |
ARP110100858A AR080760A1 (en) | 2010-03-19 | 2011-03-17 | METHOD TO TREAT HAIR |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CNPCT/CN2010/071157 | 2010-03-19 | ||
CN2010071157 | 2010-03-19 |
Publications (1)
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WO2011113249A1 true WO2011113249A1 (en) | 2011-09-22 |
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Family Applications (4)
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PCT/CN2010/075833 WO2011113249A1 (en) | 2010-03-19 | 2010-08-10 | Method of treating hair |
PCT/CN2010/075834 WO2011113250A1 (en) | 2010-03-19 | 2010-08-10 | Method of treating hair |
PCT/EP2011/052735 WO2011113676A2 (en) | 2010-03-19 | 2011-02-24 | Method of treating hair |
PCT/EP2011/052733 WO2011113675A2 (en) | 2010-03-19 | 2011-02-24 | Method of treating hair |
Family Applications After (3)
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PCT/CN2010/075834 WO2011113250A1 (en) | 2010-03-19 | 2010-08-10 | Method of treating hair |
PCT/EP2011/052735 WO2011113676A2 (en) | 2010-03-19 | 2011-02-24 | Method of treating hair |
PCT/EP2011/052733 WO2011113675A2 (en) | 2010-03-19 | 2011-02-24 | Method of treating hair |
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EP (2) | EP2547319A2 (en) |
JP (2) | JP2013522256A (en) |
CN (2) | CN102844019A (en) |
AR (2) | AR080761A1 (en) |
AU (2) | AU2011229416A1 (en) |
BR (2) | BR112012023598A2 (en) |
EA (2) | EA201290934A1 (en) |
TW (2) | TW201138892A (en) |
WO (4) | WO2011113249A1 (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101531904B1 (en) * | 2010-10-13 | 2015-06-29 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
DE102011119729A1 (en) * | 2011-11-30 | 2013-06-06 | S & V Technologies Ag | Polymerizable dyes and their compositions for ophthalmological applications |
JP5919021B2 (en) * | 2012-02-15 | 2016-05-18 | 花王株式会社 | Pigment water dispersion for inkjet recording |
FR3014686B1 (en) | 2013-12-13 | 2016-11-25 | Oreal | PROCESS FOR COLORING KERATINIC MATERIALS FROM OLIGOMERS AND / OR COLOR POLYMERS FROM SELF-OXIDIZABLE COMPOUNDS, COMPOSITION AND COLORING AGENT |
FR3014685B1 (en) | 2013-12-13 | 2016-11-25 | Oreal | PROCESS FOR COLORING KERATINIC MATERIALS FROM OLIGOMERS AND / OR COLOR POLYMERS FROM METAPHENYLENEDIAMINES, COMPOSITION, AND COLORING AGENT |
CN106414617A (en) * | 2014-05-21 | 2017-02-15 | 罗利克有限公司 | Polymerizable dichroic dyes |
EP3015135B1 (en) | 2014-10-29 | 2020-09-09 | Noxell Corporation | Hair colouration with a cationic or anionic coloured polymer, method and kit thereof |
EP3015134B1 (en) | 2014-10-29 | 2020-08-26 | Noxell Corporation | Hair colouration with a cationic coloured polymer, method and kit thereof |
WO2020033501A1 (en) * | 2018-08-07 | 2020-02-13 | Michael Milbocker | Polymeric hair color composition |
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EP1454614A1 (en) * | 2003-03-06 | 2004-09-08 | KPSS-Kao Professional Salon Services GmbH | Composition for dyeing human hair |
US20050268405A1 (en) * | 2004-05-28 | 2005-12-08 | Gaelle Brun | Composition for dyeing keratin fibers, comprising at least one pigment and polymers capable of reacting with each other to form covalent bonds |
US20070033744A1 (en) * | 2005-06-29 | 2007-02-15 | Sylvain Kravtchenko | Composition for simultaneously bleaching and dyeing keratin fibers, comprising at least one anionic or nonionic direct dye and at least one associative polymer |
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NL283797A (en) * | 1961-10-05 | |||
FR1498464A (en) * | 1965-09-06 | 1967-10-20 | Oreal | New colored resins, lacquers and colored styling lotions for hair, based on these resins |
FR2361447A1 (en) | 1976-08-12 | 1978-03-10 | Oreal | COLORING COMPOUNDS CONSISTING OF WATER-SOLUBLE CATIONIC POLYMERS AND TINCTORIAL COMPOSITIONS CONTAINING THEM |
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-
2010
- 2010-08-10 WO PCT/CN2010/075833 patent/WO2011113249A1/en active Application Filing
- 2010-08-10 WO PCT/CN2010/075834 patent/WO2011113250A1/en active Application Filing
-
2011
- 2011-02-24 WO PCT/EP2011/052735 patent/WO2011113676A2/en active Application Filing
- 2011-02-24 AU AU2011229416A patent/AU2011229416A1/en not_active Abandoned
- 2011-02-24 EA EA201290934A patent/EA201290934A1/en unknown
- 2011-02-24 JP JP2012557467A patent/JP2013522256A/en not_active Withdrawn
- 2011-02-24 BR BR112012023598A patent/BR112012023598A2/en not_active IP Right Cessation
- 2011-02-24 EP EP11706522A patent/EP2547319A2/en not_active Withdrawn
- 2011-02-24 EA EA201290925A patent/EA201290925A1/en unknown
- 2011-02-24 CN CN2011800148662A patent/CN102844019A/en active Pending
- 2011-02-24 BR BR112012023498A patent/BR112012023498A2/en not_active Application Discontinuation
- 2011-02-24 JP JP2012557466A patent/JP2013522255A/en not_active Withdrawn
- 2011-02-24 CN CN2011800148677A patent/CN102844020A/en active Pending
- 2011-02-24 EP EP11705872A patent/EP2547321A2/en not_active Withdrawn
- 2011-02-24 WO PCT/EP2011/052733 patent/WO2011113675A2/en active Application Filing
- 2011-02-24 AU AU2011229417A patent/AU2011229417A1/en not_active Abandoned
- 2011-03-03 TW TW100107215A patent/TW201138892A/en unknown
- 2011-03-03 TW TW100107214A patent/TW201138853A/en unknown
- 2011-03-17 AR ARP110100859A patent/AR080761A1/en not_active Application Discontinuation
- 2011-03-17 AR ARP110100858A patent/AR080760A1/en not_active Application Discontinuation
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EP1454614A1 (en) * | 2003-03-06 | 2004-09-08 | KPSS-Kao Professional Salon Services GmbH | Composition for dyeing human hair |
US20050268405A1 (en) * | 2004-05-28 | 2005-12-08 | Gaelle Brun | Composition for dyeing keratin fibers, comprising at least one pigment and polymers capable of reacting with each other to form covalent bonds |
US20070033744A1 (en) * | 2005-06-29 | 2007-02-15 | Sylvain Kravtchenko | Composition for simultaneously bleaching and dyeing keratin fibers, comprising at least one anionic or nonionic direct dye and at least one associative polymer |
Also Published As
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AR080761A1 (en) | 2012-05-09 |
EP2547321A2 (en) | 2013-01-23 |
EA201290934A1 (en) | 2013-04-30 |
EA201290925A1 (en) | 2013-03-29 |
AU2011229416A1 (en) | 2012-10-11 |
JP2013522256A (en) | 2013-06-13 |
CN102844019A (en) | 2012-12-26 |
TW201138853A (en) | 2011-11-16 |
WO2011113250A1 (en) | 2011-09-22 |
CN102844020A (en) | 2012-12-26 |
AR080760A1 (en) | 2012-05-09 |
WO2011113676A2 (en) | 2011-09-22 |
BR112012023598A2 (en) | 2016-08-02 |
WO2011113676A3 (en) | 2012-05-31 |
BR112012023498A2 (en) | 2016-05-31 |
WO2011113675A2 (en) | 2011-09-22 |
AU2011229417A1 (en) | 2012-10-11 |
EP2547319A2 (en) | 2013-01-23 |
WO2011113675A3 (en) | 2012-05-31 |
JP2013522255A (en) | 2013-06-13 |
TW201138892A (en) | 2011-11-16 |
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