WO2011113250A1 - Procédé de traitement capillaire - Google Patents

Procédé de traitement capillaire Download PDF

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Publication number
WO2011113250A1
WO2011113250A1 PCT/CN2010/075834 CN2010075834W WO2011113250A1 WO 2011113250 A1 WO2011113250 A1 WO 2011113250A1 CN 2010075834 W CN2010075834 W CN 2010075834W WO 2011113250 A1 WO2011113250 A1 WO 2011113250A1
Authority
WO
WIPO (PCT)
Prior art keywords
dye
blue
acid
polymer
composition
Prior art date
Application number
PCT/CN2010/075834
Other languages
English (en)
Inventor
Stephen Norman Batchelor
Jayne Michelle Bird
Wei Chen
Qingsheng Tao
Jinfang Wang
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 EA201290925A priority Critical patent/EA201290925A1/ru
Priority to EP11706522A priority patent/EP2547319A2/fr
Priority to AU2011229416A priority patent/AU2011229416A1/en
Priority to JP2012557466A priority patent/JP2013522255A/ja
Priority to CN2011800148662A priority patent/CN102844019A/zh
Priority to BR112012023498A priority patent/BR112012023498A2/pt
Priority to PCT/EP2011/052733 priority patent/WO2011113675A2/fr
Priority to TW100107214A priority patent/TW201138853A/zh
Priority to ARP110100859A priority patent/AR080761A1/es
Publication of WO2011113250A1 publication Critical patent/WO2011113250A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • 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 WO2009/090 21 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 poiymer is obtainable preferably obtained by the reaction of a NH 2 group directly and covalently bound to an aromatic ring of a dye i) with a reactive group of a monomeric compound ii) in which the reactive group is selected from the group consisting of isocyanate; oxazolone; epoxide; ester, and anhydride, followed by polymerising the resulting dye monomer to form a dye polymer iii).
  • the resulting dye monomer is then polymerised with other suitable monomers to form the dye- polymer.
  • the NH 2 group of a dye is reacted with a monomer containing a reactive group selected from: isocyanate; oxazolone ester and epoxide.
  • a reactive group selected from: isocyanate; oxazolone ester and epoxide.
  • the reactive group of the monomer is an epoxide.
  • the ring-opening reaction of epoxide group with amine can be accelerated by some acidic catalysts.
  • R groups include
  • Z is an organic group containing an unsaturated carbon, carbon double bond.
  • Z is an acrylate or a styrene, more preferable Z is an acrylate.
  • Preferred monomers for reaction with the dye are glycidyl acrylate, 2-glycidyl methacrylate, 2-vinyl-4,4-dimethyl-5-oxazolone, vinyl isocyanate, 2-isocyanatoethyl methacrylate, N-methacryloxysuccinimide.
  • the dye must contain an NH 2 group covalently bound to an aromatic ring of the dye.
  • the NH 2 is covalently 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 polymerisabie double bonds.
  • a dye containing a reactive groups is made up of a chromophore which is linked 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, difluorotriazlne, monochlorotriazinyl, bromoacrlyamide and trichloropyrimidine.
  • Dyes are organic molecules that have an absorption coefficient of greater than 4000, preferably greater than 10 000 mol "1 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, thphenyl 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 dye polymer is formed by polymerization of the dye monomer, preferably with suitable co-monomer.
  • the dye-polymer contains 0.1 to 30 Molar% dye units, more preferably 1 to 15 Molar% dye monomers units, most preferably 2 to 10 Molar%.
  • the polymeric compound within the dye polymer is covalently 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 dye is preferably uncharged or anionic charged. 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 cationic or anionic charges.
  • Co-monomers may be selected from any suitable alkenes, acrylates and styrenes are particularly preferred. Suitable co-monomers include diethylaminoethylmethacrylate, dimethylaminopropyl metacryamide, methyl vinylether, methacrylic acid, 2-acrylamido-2-methyl-1-propanesulfonic acid, 2- hydroxyethyl acrylate; 2-hydroxyethyl methacrylate dimethylaminoethyl methacrylate, methyl methacrylate, methyl acrylate, hydroxyethyl methacrylate, 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
  • 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 should have a molecular weight 2000 and greater. Preferred ranges are from 2000 to 500 000, more preferred ranges are from 2000 to 20 000. In this context the molecular weight is the number average molecular weight.
  • 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.
  • 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 is 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
  • the dye monomer was synthesised by heating 1g of the anthraquinone dye with 0.5ml of the epoxide monomer for 3 hours in 20 ml of acetic acid. Following reaction the dye-monomer was purified and 0.15g of its polymerised with 3 g of co-monomer in tetrahydrofuran as shown below.
  • the polymer was coded P1
  • the polymers were code P2 and P3 respectively.
  • 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.
  • 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 remeasured.
  • the results are summarised beiow.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Coloring (AREA)

Abstract

La présente invention concerne un procédé de coloration des cheveux, qui comprend l'étape d'application sur les cheveux d'une composition comprenant un polymère colorant. Le polymère colorant est obtenu en faisant réagir un groupe NH2 lié directement et de manière covalente à un noyau aromatique d'un colorant i) avec un groupe réactif d'un composé monomère ii), le groupe réactif étant sélectionné dans le groupe constitué d'isocyanate, d'oxazolone, d'ester et d'époxyde, puis en provoquant la polymérisation du monomère de colorant obtenu pour former un polymère colorant iii).
PCT/CN2010/075834 2010-03-19 2010-08-10 Procédé de traitement capillaire WO2011113250A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
EA201290925A EA201290925A1 (ru) 2010-03-19 2011-02-24 Способ обработки волос
EP11706522A EP2547319A2 (fr) 2010-03-19 2011-02-24 Méthode de traitement des cheveux
AU2011229416A AU2011229416A1 (en) 2010-03-19 2011-02-24 Method of treating hair
JP2012557466A JP2013522255A (ja) 2010-03-19 2011-02-24 毛髪の処理方法
CN2011800148662A CN102844019A (zh) 2010-03-19 2011-02-24 处理毛发的方法
BR112012023498A BR112012023498A2 (pt) 2010-03-19 2011-02-24 método para tingimento de cabelos
PCT/EP2011/052733 WO2011113675A2 (fr) 2010-03-19 2011-02-24 Méthode de traitement des cheveux
TW100107214A TW201138853A (en) 2010-03-19 2011-03-03 Method of treating hair
ARP110100859A AR080761A1 (es) 2010-03-19 2011-03-17 Metodo para tratar el cabello

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN2010071157 2010-03-19
CNPCT/CN2010/071157 2010-03-19

Publications (1)

Publication Number Publication Date
WO2011113250A1 true WO2011113250A1 (fr) 2011-09-22

Family

ID=44625256

Family Applications (4)

Application Number Title Priority Date Filing Date
PCT/CN2010/075833 WO2011113249A1 (fr) 2010-03-19 2010-08-10 Procédé de traitement capillaire
PCT/CN2010/075834 WO2011113250A1 (fr) 2010-03-19 2010-08-10 Procédé de traitement capillaire
PCT/EP2011/052735 WO2011113676A2 (fr) 2010-03-19 2011-02-24 Méthode de traitement des cheveux
PCT/EP2011/052733 WO2011113675A2 (fr) 2010-03-19 2011-02-24 Méthode de traitement des cheveux

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/CN2010/075833 WO2011113249A1 (fr) 2010-03-19 2010-08-10 Procédé de traitement capillaire

Family Applications After (2)

Application Number Title Priority Date Filing Date
PCT/EP2011/052735 WO2011113676A2 (fr) 2010-03-19 2011-02-24 Méthode de traitement des cheveux
PCT/EP2011/052733 WO2011113675A2 (fr) 2010-03-19 2011-02-24 Méthode de traitement des cheveux

Country Status (9)

Country Link
EP (2) EP2547319A2 (fr)
JP (2) JP2013522256A (fr)
CN (2) CN102844020A (fr)
AR (2) AR080760A1 (fr)
AU (2) AU2011229416A1 (fr)
BR (2) BR112012023598A2 (fr)
EA (2) EA201290934A1 (fr)
TW (2) TW201138853A (fr)
WO (4) WO2011113249A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2020033501A1 (fr) * 2018-08-07 2020-02-13 Michael Milbocker Composition de coloration capillaire polymère

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101531904B1 (ko) * 2010-10-13 2015-06-29 롬엔드하스전자재료코리아유한회사 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
DE102011119729A1 (de) * 2011-11-30 2013-06-06 S & V Technologies Ag Polymerisierbare Farbstoffe und deren Zusammensetzungen für opthalmologische Anwendungen
JP5919021B2 (ja) * 2012-02-15 2016-05-18 花王株式会社 インクジェット記録用顔料水分散液
FR3014686B1 (fr) 2013-12-13 2016-11-25 Oreal Procede de coloration des matieres keratiniques a partir d'oligomeres et/ou de polymeres colores issus de composes auto-oxydables, composition et agent de coloration
FR3014685B1 (fr) 2013-12-13 2016-11-25 Oreal Procede de coloration des matieres keratiniques a partir d'oligomeres et/ou de polymeres colores issus de metaphenylenediamines, composition, et agent de coloration
KR102391559B1 (ko) * 2014-05-21 2022-04-29 롤리크 아게 중합가능한 이색성 염료

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4182612A (en) * 1977-01-31 1980-01-08 The Gillette Company Method for dyeing human hair with cationic polymeric dyes
WO2002090447A1 (fr) * 2001-05-08 2002-11-14 Rolic Ag Melange dichroique
WO2008009579A1 (fr) * 2006-07-18 2008-01-24 Ciba Holding Inc. Colorants polymères pour cheveux
WO2009090125A1 (fr) * 2008-01-17 2009-07-23 Basf Se Colorants capillaires polymères

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NL283797A (fr) * 1961-10-05
LU51345A1 (fr) * 1966-06-16 1967-12-18
DE1794352C3 (de) * 1961-10-05 1979-09-27 L'oreal, Paris Verwendung von gefärbten Polymerisaten als färbender Bestandteil in Haarfärbemitteln
FR1498464A (fr) * 1965-09-06 1967-10-20 Oreal Nouvelles résines colorées, laques et lotions de mise en plis colorées pour cheveux, à base de ces résines
FR2361447A1 (fr) 1976-08-12 1978-03-10 Oreal Composes colorants constitues de polymeres cationiques hydrosolubles et compositions tinctoriales les contenant
FR2456764A2 (fr) 1979-05-18 1980-12-12 Oreal Nouveaux polymeres colorants, leur preparation et leur utilisation
US6306182B1 (en) * 1999-12-29 2001-10-23 Revlon Consumer Products Corporation Polymeric dye compounds and compositions and methods for coloring hair
DE10309523A1 (de) * 2003-03-05 2004-09-16 Wella Ag Mittel und Verfahren zum Färben von Keratinfasern
DE60315945T2 (de) * 2003-03-06 2008-07-31 Kpss-Kao Professional Salon Services Gmbh Zusammensetzung zum Färben von menschlichen Haaren
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
US7799092B2 (en) * 2005-06-29 2010-09-21 L'oreal S.A. Composition for simultaneously bleaching and dyeing keratin fibers, comprising at least one anionic or nonionic direct dye and at least one associative polymer
ES2438280T3 (es) 2008-01-17 2014-01-16 Basf Se Tintes poliméricos capilares

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4182612A (en) * 1977-01-31 1980-01-08 The Gillette Company Method for dyeing human hair with cationic polymeric dyes
WO2002090447A1 (fr) * 2001-05-08 2002-11-14 Rolic Ag Melange dichroique
WO2008009579A1 (fr) * 2006-07-18 2008-01-24 Ciba Holding Inc. Colorants polymères pour cheveux
WO2009090125A1 (fr) * 2008-01-17 2009-07-23 Basf Se Colorants capillaires polymères

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2020033501A1 (fr) * 2018-08-07 2020-02-13 Michael Milbocker Composition de coloration capillaire polymère

Also Published As

Publication number Publication date
WO2011113676A3 (fr) 2012-05-31
WO2011113675A2 (fr) 2011-09-22
TW201138892A (en) 2011-11-16
AU2011229417A1 (en) 2012-10-11
BR112012023498A2 (pt) 2016-05-31
JP2013522256A (ja) 2013-06-13
BR112012023598A2 (pt) 2016-08-02
EP2547319A2 (fr) 2013-01-23
JP2013522255A (ja) 2013-06-13
CN102844019A (zh) 2012-12-26
WO2011113676A2 (fr) 2011-09-22
WO2011113675A3 (fr) 2012-05-31
TW201138853A (en) 2011-11-16
EA201290934A1 (ru) 2013-04-30
EP2547321A2 (fr) 2013-01-23
EA201290925A1 (ru) 2013-03-29
AR080761A1 (es) 2012-05-09
AR080760A1 (es) 2012-05-09
AU2011229416A1 (en) 2012-10-11
CN102844020A (zh) 2012-12-26
WO2011113249A1 (fr) 2011-09-22

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