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EP2547320A2 - Composition - Google Patents

Composition

Info

Publication number
EP2547320A2
EP2547320A2 EP11704992A EP11704992A EP2547320A2 EP 2547320 A2 EP2547320 A2 EP 2547320A2 EP 11704992 A EP11704992 A EP 11704992A EP 11704992 A EP11704992 A EP 11704992A EP 2547320 A2 EP2547320 A2 EP 2547320A2
Authority
EP
European Patent Office
Prior art keywords
polymer
dye
reactive
pei
composition
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP11704992A
Other languages
German (de)
English (en)
Inventor
Stephen Norman Batchelor
Sheng MENG
Andrew Malcolm Murray
Qingsheng Tao
Jinfang Wang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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 NV filed Critical Unilever PLC
Publication of EP2547320A2 publication Critical patent/EP2547320A2/fr
Withdrawn legal-status Critical Current

Links

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
    • A61K8/72—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
    • 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
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
    • 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 using said composition.
  • US 4 182 612 discloses polyethylenimine cationic polymers covalently linked to dyes for the colouration of hair. The dyes used do not carry negatively charged substituents.
  • 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.
  • US 4 228 259 discloses a dye for keratinic material comprises a water- soluble cationic polymer.
  • WO2008/009579 (Ciba) and WO2009/090121 to WO2009/090125 (BASF) disclose cationic dyes covalently linked to polymers for the colouration of hair.
  • the present invention provides a composition according to claim 1 .
  • the polymer comprises a free -SH, -OH or -NH 2 group for reaction with the dye. More preferably, the polymer contains at least one -OH or -NH 2 group.
  • the polymers have an overall cationic charged at pH 5.0.
  • the polymer comprises quaternary amine groups or tertiary amines. Examples of such polymers are polyethyleneimine, polypropylene- imine, polyvinylannine; polyvinylinnine, aminosilcone, cationic modified starch and cationic modified polyvinylalcohol.
  • the polymer has a molecular weight of from 500 to 200 000.
  • the polymer is a polyamine.
  • the polyamine is selected from polyethyleneimine, polypropylene- imine, polyvinylannine, and polyvinylinnine.
  • 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
  • PEI polyethyleneimine
  • polyamines are ethoxylated to provide ethoxylated
  • polyethyleneimine EPEI
  • EPEI 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 2 to about 60000, more preferably from about 3 to about 24000 and y is an integer from about 1 to about 60000, preferably from about 2 to about 30000, more preferably from about 3 to about 12000.
  • polyethylene imines are PEI-3, PEI-7, PEI-15, PEI-30, PEI-45, PEI-100, 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, PEI-70000, PEI-500000, PEI-5000000 and the like, wherein the integer represents the average molecular weight of the polymer.
  • PEI's which are designated as such are available through Aldrich.
  • the PEI before alkoxylation and/or reaction with a reactive dye, has an average molecular weight of from 800 to 8000.
  • the PEI is preferably alkoxylated, most preferably ethoxylated.
  • 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.
  • 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).
  • the reactive dye comprises a reactive group selected from
  • dichlorotriazinyl difluorochloropyrimidine, monofluorotrazinyl, dichloroquinoxaline, vinylsulfone, difluorotriazine, monochlorotriazinyl, bromoacrlyamide and
  • the reactive dye comprises a reactive group selected from monochlorotriazinyl, dichlorotriazinyl, and vinylsulfonyl.
  • the reactive dye comprises a chromophore selected from azo, anthraquinone, phthalocyanine, formazan and triphendioaxazine. More preferably from azo, anthraquinone, phthalocyanine, and triphendioaxazine. Most preferably from azo and anthraquinone.
  • the dye is an azo dye it is preferred that the azo dye is not an azo-metal complex dye.
  • reactive dyes examples include reactive black 5, reactive blue 19, reactive red 2, reactive blue 59, reactive blue 269, reactive blue 1 1 , reactive yellow 17, reactive, reactive orange 4, reactive orange 16, reactive green 19, reactive brown 2, reactive brown 50.
  • the dye contains one, two, three or four SOsNa groups, more preferably one or two. This provides a beneficial level of negative charge.
  • Combination of reactive dyes may be used to obtain a wide colour palette with use of a limited number of dyes.
  • a trichromate system consisting of a mixture of three reactive dyes.
  • the trichromate system contains a combination of a reactive blue or a reactive black dye, a reactive red and a reactive yellow dye.
  • reactive black 5, reactive yellow 176 and reactive red 239; reactive blue 176, reactive yellow 176 and reactive red 141 .
  • each polymer molecule should be covalently bound to at least one dye molecule, preferably more than two.
  • the dye polymer is obtainable by reacting the polymer with 0.1 -20wt% reactive dye, most preferably 1 to 10wt%.
  • the composition comprises a peroxide source to allow bleaching and dyeing simultaneously. Suitable peroxide sources include hydrogen peroxide.
  • the composition is a rinse-off hair treatment composition.
  • the composition comprises from 5 to 35% wt. anionic surfactant.
  • Suitable anionic surfactants include the alkali-metal alkyl ether sulphates where the alkyl group comprises from 8 to 18 carbon atoms. Preferred anionic
  • surfactants include sodium lauryl ether sulphate with 1 , 2 or 3 EO groups, preferably 1 EO group.
  • the composition comprises a pearlescer.
  • Suitable pearlescers include ethylene glycol distearate.
  • the composition is packaged in a closable bottle.
  • the composition is a shampoo, conditioner or hair treatment
  • composition where the composition is a hair conditioning composition it will comprise a conditioning active such as fatty alcohol or fatty acid or fatty ester or fatty amide, a cationic surfactant or silicone.
  • a conditioning active such as fatty alcohol or fatty acid or fatty ester or fatty amide, a cationic surfactant or silicone.
  • PEG MeO-methyl glycidyl ether was synthesized as shown by the reaction schme.
  • EPEI polymer were synthesized by mixing PEG MeO-methyl glycidyl ether with PEI in methanol and refluxing for 4 days. The viscous product was obtained after dialysis in water and lyophilisation.
  • a 1 wt% solution of the dye polymers was made in demineralised water.
  • a 3 by 10cm knitted woollen swatch (sheep) was place into the dye-polymer solution and agitated for 20seconds, removed and dried.
  • the colour of the wool 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 30 seconds under a running tap, dried and the colour re-measured.
  • the swatch was then washed in shampoo, rinsed, dried and re-measured. The results are shown below
  • C * is a comparative example of a neutral polymer (hydroxyethyl cellulose) with reactive dyes) synthesised as follows 0.5g of hydroxyethylcellulose, 0.5g Na 2 CO3 and 0.05g of reactive dye (0.040g Reactive Blue 4 and 0.01 Og Reactive Red 2) were mixed together in 100ml of demineralised water and heated at 60°C for 5 hours. Following the reaction the product was dialyzed against water
  • the shampoo used was of the following formula: 20wt% Sodium lauryl ether sulphate; 5.3wt% cocoamidopropyl betaine; 6.5wt% Mirasheen A-220 (ex Rhodia) which is a mix of Glycol Distearate, Ammonium Laureth Sulfate, Amonium Lauryl Sulfate, Cocamide MEA, Ammonium Xylene Sulfonate; remainder minors and water.
  • Example 5 20wt% Sodium lauryl ether sulphate; 5.3wt% cocoamidopropyl betaine; 6.5wt% Mirasheen A-220 (ex Rhodia) which is a mix of Glycol Distearate, Ammonium Laureth Sulfate, Amonium Lauryl Sulfate, Cocamide MEA, Ammonium Xylene Sulfonate; remainder minors and water.
  • compositions made by standard processes are compositions made by standard processes.
  • Polymer A PEI reacted with 2.5wt% of reactive black 5
  • Polymer B PEI reacted with 2.5wt% reactive yellow 176
  • Polymer C PEI reacted 2.5wt% with reactive red 239

Landscapes

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

Abstract

La présente invention concerne une composition pour les cheveux qui comprend un colorant polymère, ledit colorant polymère comprenant un polymère à charge positive et un colorant réactif à charge négative. La présente invention concerne également un procédé de coloration des cheveux par application d'une composition comprenant un colorant polymère, ledit colorant polymère comprenant un polymère à charge positive et un colorant réactif à charge négative.
EP11704992A 2010-03-19 2011-02-25 Composition Withdrawn EP2547320A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN2010071156 2010-03-19
PCT/EP2011/052841 WO2011113680A2 (fr) 2010-03-19 2011-02-25 Composition

Publications (1)

Publication Number Publication Date
EP2547320A2 true EP2547320A2 (fr) 2013-01-23

Family

ID=44625196

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11704992A Withdrawn EP2547320A2 (fr) 2010-03-19 2011-02-25 Composition

Country Status (9)

Country Link
EP (1) EP2547320A2 (fr)
JP (1) JP2013522258A (fr)
AR (1) AR080759A1 (fr)
AU (1) AU2011229421A1 (fr)
BR (1) BR112012023599A2 (fr)
EA (1) EA201290927A1 (fr)
PH (1) PH12012501795A1 (fr)
TW (1) TW201138848A (fr)
WO (1) WO2011113680A2 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012119811A2 (fr) 2011-03-10 2012-09-13 Unilever Plc Composition
WO2012119810A2 (fr) 2011-03-10 2012-09-13 Unilever Plc Composition
WO2012119821A2 (fr) * 2011-03-10 2012-09-13 Unilever Plc Composition
JP6225008B2 (ja) 2012-12-26 2017-11-01 花王株式会社 毛髪洗浄剤
WO2014111280A1 (fr) * 2013-01-15 2014-07-24 Unilever Plc Composition
EP2945708A1 (fr) * 2013-01-15 2015-11-25 Unilever PLC Composition
EP2945707A1 (fr) * 2013-01-15 2015-11-25 Unilever PLC Composition
EA032098B1 (ru) * 2014-04-14 2019-04-30 Юнилевер Н.В. Композиция для ухода за кожей
EA031724B1 (ru) * 2014-04-14 2019-02-28 Юнилевер Н.В. Композиция для ухода за кожей
EP3015134B1 (fr) * 2014-10-29 2020-08-26 Noxell Corporation Coloration capillaire à partir d'un colorant polymérique cationique, procédé et kit pour celle-ci
EP3015135B1 (fr) * 2014-10-29 2020-09-09 Noxell Corporation Coloration capillaire avec un polymère coloré cationique ou anionique, procédé et kit pour celui-ci
GB2561014B (en) * 2017-04-02 2020-04-22 Henkel Kgaa Compositions and methods for coloring fibers
KR102636575B1 (ko) 2019-09-26 2024-02-15 주식회사 엘지생활건강 아민 개질 폴리올을 포함하는 염색모의 색 빠짐 방지 및 모발 염색용 조성물

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2361447A1 (fr) 1976-08-12 1978-03-10 Oreal Composes colorants constitues de polymeres cationiques hydrosolubles et compositions tinctoriales les contenant
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
US4381260A (en) * 1981-07-17 1983-04-26 Union Carbide Corporation Aromatic chromophoric substituted polysiloxane dyes
US4911731A (en) * 1983-02-22 1990-03-27 Clairol Incorporated Process and composition for dyeing hair utilizing an anionic polymeric/cationic polymer complex
US7731761B2 (en) 2006-07-18 2010-06-08 Ciba Corporation Polymeric hair dyes
EP2073786A2 (fr) * 2006-09-15 2009-07-01 L'Oreal Procede de coloration des cheveux non rince a partir d'une composition comprenant un polymere colore et actif cosmetique
JP5539226B2 (ja) 2008-01-17 2014-07-02 ビーエーエスエフ ソシエタス・ヨーロピア ポリマー毛髪染料
KR101693050B1 (ko) 2008-01-17 2017-01-04 바스프 에스이 중합체성 모발 염료

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2011113680A2 *

Also Published As

Publication number Publication date
WO2011113680A2 (fr) 2011-09-22
PH12012501795A1 (en) 2012-12-10
AU2011229421A1 (en) 2012-10-04
WO2011113680A3 (fr) 2012-05-31
EA201290927A1 (ru) 2013-02-28
BR112012023599A2 (pt) 2016-08-02
TW201138848A (en) 2011-11-16
JP2013522258A (ja) 2013-06-13
AR080759A1 (es) 2012-05-09

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