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GB2168082A - Dye compositions - Google Patents

Dye compositions Download PDF

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Publication number
GB2168082A
GB2168082A GB08517349A GB8517349A GB2168082A GB 2168082 A GB2168082 A GB 2168082A GB 08517349 A GB08517349 A GB 08517349A GB 8517349 A GB8517349 A GB 8517349A GB 2168082 A GB2168082 A GB 2168082A
Authority
GB
United Kingdom
Prior art keywords
composition
dye
composition according
weight
cationic surfactant
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.)
Granted
Application number
GB08517349A
Other versions
GB2168082B (en
GB8517349D0 (en
Inventor
Terry Francis Houiellebecq
Martin Edwin Day
Anne Lilian Wilkins
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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
Priority claimed from GB848419518A external-priority patent/GB8419518D0/en
Priority claimed from GB858501115A external-priority patent/GB8501115D0/en
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Publication of GB8517349D0 publication Critical patent/GB8517349D0/en
Publication of GB2168082A publication Critical patent/GB2168082A/en
Application granted granted Critical
Publication of GB2168082B publication Critical patent/GB2168082B/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/731Cellulose; Quaternized cellulose derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817Compositions 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/896Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42Colour properties
    • A61K2800/43Pigments; Dyes
    • A61K2800/432Direct dyes

Landscapes

  • 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)

Abstract

A dye composition for treating hair contains a cationic surfactant, a direct dye and a liquid vehicle. The colour intensity of the dye is increased by the use of cationic surfactants. Amphoteric surfactants are incorporated to increase foam producing ability without reducing to any great extent the dyeing capability.

Description

SPECIFICATION Compositions The present invention relates to dye compositions useful in dyeing natural fibres, and in particular for dyeing human hair.
Direct dyes are commonly used to colour fibrous materials, for instance human hair, for a limited time and may be useful when repeated changes in colour are required. However, direct dyes often impart a low colour intensity to a substrate and safety considerations may prevent the use of more concentrated compositions.
It has now been found that the colour intensity of direct dyes deposited onto human hair can be increased by the use of cationic surfactants, the surfactants facilitating higher deposition of dye onto the hair.
Accordingly, the present invention provides a dye composition for treating hair, comprising a cationic surfactant, a direct dye and a liquid vehicle. Preferably the liquid vehicle is an aqueous vehicle.
Examples of direct dyes include anthraquinone, azo, nitro, basic, triarylmethane, or disperse dyes or any combination thereof.
Anthraquinone dyes are those containing the group
and a particular example is Disperse Blue No. 1, of formula
Azo dyes are those containing the -N=N- group, and a particular example is Disperse Orange No. 3, of formula
Nitro dyes are those containing the -NO2 group, and a particular example is 2 nitro-pphenylene diamine, of formula
Basic dyes are those containing coloured cations, and a particular example is Basic Yellow 9, of formula
Triarylmethane dyes are those containing the group
and a particular example is Basic Violet 14, of formula
Disperse dyes are those which are substantially insoluble in water and are used as a dispersion in the medium.A particular example is Disperse Yellow 1 of formula
The cationic surfactants for use in the composition of the invention include: quanternised cellulose derivatives, polypropoxylated dialkyl ammonium chloride, quarternised silicone derivatives, diamino functional silicones, polyhalide salts of polyionenes terminated with triethanolammonium groups, quarternised derivatives of gluconic acid, and quaternary oleyl amine esters.
Preferably the cationic surfactant is a quaternised silicone derivative, diamino functional silicone or a polypropoxylated dialkyl ammonium chloride. Preferred diamino functional silicones are those of general formula (I)
in which X and Y, which may be the same or different, are each Cl 6 alkyl, preferably y -CH3, or -OH, R is C13 alkyl and m and n are each integers of from 1 to 100.
A particularly preferred compound of formula (I) is Amodimethicone, manufactured by Dow Corning as DC929 emulsion.
Preferably, the compounds of formula (I) are used in the form of emulsions.
The quaternised silicone derivatives may be soluble or insoluble in the liquid vehicle. When insoluble they will preferably be present as emulsions.
In a preferred form of the invention the liquid vehicle and the cationic surfactant comprise a conditioner base.
The compositions of the invention may optionally include further surfactants which may be cationic or non-ionic to modify the antistatic, combability and gloss properties of the substrate.
Hitherto, it has been found desirable, for consumer appeal, to provide dye compositions which generate some foam during use. However, this can reduce the dyeing efficiency of the composition, We have found that by including in the composition amphoteric surfactants with foam producing ability, there is little or no reduction in dyeing capability. Accordingly, in a further aspect of the present invention, the dye composition of the invention additionally contains an amphoteric surfactant. Preferred surfactants are those of the betaine type, such as long chain alkyl betaines or long chain alkyl amido alkyl betaines, and they are preferably present in an amount of from 0.1 to 5% by weight of the composition.
The total cationic surfactant content of the composition of the invention is preferably within the range of 0.1 to 10% by weight of the composition, more preferably 0.1 to 5% by weight, and particularly 0.1 to 3% by weight.
The total dye content is preferably in the range 0.01 to 10% by weight of the composition.
Suitably the dye, or when a mixture of dyes is used, each dye, may be present in the composition of the invention at from 0.01 to 5% by weight, preferably 0.01 to 3%.
The non-ionic surfactants may be present in the composition of the invention at from 0.1 to 5% by weight of the composition. Total non-ionic surfactant content is preferably in the range of from 0.1 to 10% by weight of the composition.
It will be appreciated that in formulating the composition, the skilled man would consider the toxicity of each component and would accordingly use a non-toxic amount of dye, cationic surfactant or any other component.
Dye compositions of the invention may also comprise conventional toiletries additives such as thickening and suspending agents, opacifiers, pearlescent agents, sequestrants, colour stabilising agents, perfumes, preservatives, glycols and other dye solubilisers.
The pH of the compositions of the invention may be from 1 to 10 preferably from 5 to 7. If necessary the pH may be adjusted using conventional agents.
When used herein the term 'liquid vehicle' includes water or water admixed with other nonaqueous liquids which together can dissolve or support the direct dye and cationic surfactant.
In a further aspect the present invention provides a process for the preparation of a dye composition, which comprises: (a) optionally dissolving thickeners in a liquid vehicle, heating if necessary to between 30 C and 90"C to effect dissolution; (b) admixing a cationic surfactant with the liquid vehicle at ambient or slightly elevated temperature; (c) admixing a direct dye with the liquid vehicle; (d) and adjusting the pH of the composition to within the range of from 4 to 10, preferably from 5 to 7.
Further toiletries additives may be added at any convenient stage in the process, preferably before final pH adjustment.
The direct dye may be in dry powder form or may be predispersed, suspended or dissolved in a suitable solvent, preferably a glycol for example glycerin or propylene glycol.
The invention further provides a method for treating non-human or human hair comprising applying an effective, non-toxic amount of composition as hereinbefore defined to the hair.
The compositions of the invention will now be illustrated by way of the following Examples.
Example 1 Weight Percent Hydroxy ethyl cellulose 0.7 Oleyl amino-bis-(2-hydroxypropyl-trimethyl ammonium chloride) 0.8 Glycerin 4.5 2-Nitro-p-phenylene diamine 0.4 Perfume qs Preservatives qs Deionised water qs to 100 Example 2 Weight Percent Hydroxy ethyl cellulose 0.7 y-GIuconamido propyl dimethyl-2 hydroxy ethyl ammonium chloride 0.2 Glycerin 4.5 N4-(2-hydroxyethyl)-2-nitro-p-phenylene diamine 0.7 Perfume qs Preservatives qs Deionised water qs to 100 Example 3 Weight Percent Hydroxy ethyl cellulose 0.7 Poly(dimethyl butenyl ammonium chloride)-a,ebis- (triethanolammonium chloride) 2.0 Glycerin 4.5 N' ,N4,N4,tris(2-hydroxyethyl)-2-nitro- p-phenylene diamine 0.4 Perfume qs Preservatives qs Deionised water qs to 100 Example 4 Weight Percent Hydroxy propyl guar 0.7 Amino functional polydimethyl siloxane (emulsified with Polyoxyethylene (10) nonyl phenyl ether) 1.0 Glycerin 4.5 N4-(2-hydroxyethyl)-2-nitro-p-phenylene diamine 0.4 4-Nitro-o-phenylene diamine 0.2 Perfume qs Preservatives qs Deionised water qs to 100 Test Procedure Compositions were evaluated by dyeing hair tresses using the following procedure: Hair tresses were prepared using virgin human hair (Ig) bound with waxed twine. The colourant composition (0.5g) was applied evenly to the dampened hair tress and allowed to penetrate for 20 minutes before being rinsed in warm water. Finally the tresses were dried with warm air and assessed in natural daylight.
Results Example Initial Final Shade 1 light brown bright red 2 light brown deep plum 3 light blonde ash-blue 4 dark brown deep burgundy

Claims (9)

1. A dye composition for treating hair, comprising a cationic surfactant, a direct dye and a liquid vehicle.
2. A composition according to claim 1, in which the cationic surfactant is selected from quaternised cellulose derivatives, polypropoxylated dialkyl ammonium chloride, quaternised silicone derivatives, diamino functional silicones, polyhalide salts of polyionenes terminated with triethanolammonium groups, quaternised derivatives of gluconic acid, and quaternary oleyl amine esters.
3. A composition according to claim 1 or claim 2, in which the direct dye is selected from anthraquinone, azo, nitro, basic, triarylmethane or disperse dyes.
4. A composition according to any one of claims 1 to 3, in which the cationic surfactant is present within a range of from 0.1 to 10% by weight of the composition.
5. A composition according to any one of claims 1 to 4, in which the total dye content is in the range 0.01 to 10% by weight of the composition.
6. A composition according to any one of claims 1 to 5, additionally comprising a non-ionic surfactant.
7. A composition according to any one of claims 1 to 6 additionally comprising an amphoteric surfactant.
8. A composition according to claim 7 wherein the amphoteric surfactant is present in an amount of from 0.1 to 5% by weight of the composition.
9. A dye composition for treating hair, substantially as hereinbefore described in any one of the Examples.
GB08517349A 1984-07-31 1985-07-09 Dye compositions Expired GB2168082B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB848419518A GB8419518D0 (en) 1984-07-31 1984-07-31 Dye compositions
GB858501115A GB8501115D0 (en) 1985-01-16 1985-01-16 Compositions

Publications (3)

Publication Number Publication Date
GB8517349D0 GB8517349D0 (en) 1985-08-14
GB2168082A true GB2168082A (en) 1986-06-11
GB2168082B GB2168082B (en) 1988-09-14

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Family Applications (1)

Application Number Title Priority Date Filing Date
GB08517349A Expired GB2168082B (en) 1984-07-31 1985-07-09 Dye compositions

Country Status (1)

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0312343A2 (en) * 1987-10-15 1989-04-19 Unilever Plc Hair treatment product
US4943430A (en) * 1986-07-30 1990-07-24 Lever Brothers Company Treatment of keratinous fibres
JPH03294217A (en) * 1990-04-10 1991-12-25 Hoyu Co Ltd Hair dye
US5281240A (en) * 1992-09-21 1994-01-25 Dow Corning Corporation Method of coloring hair with water soluble acid dyes
FR2713927A1 (en) * 1993-12-22 1995-06-23 Oreal Process for the direct dyeing of human keratin fibers using water vapor
FR2724560A1 (en) * 1994-09-21 1996-03-22 Oreal PROCESS FOR DIRECT COLORING OF KERATIN FIBERS USING CATIONIC DIRECT DYES AND WATER VAPOR
EP0756861A2 (en) * 1995-07-31 1997-02-05 Kao Corporation Composition for dyeing of human hair
WO1999011227A1 (en) * 1997-09-04 1999-03-11 Cognis Deutschland Gmbh Use of ester quaternaries as emulsifiers for producing preparations for coloring keratin fibers
WO2000012057A1 (en) * 1998-08-26 2000-03-09 L'oreal Dyeing composition for keratinous fibres with a cationic direct colouring agent and a silicone
DE19758272C5 (en) * 1997-12-31 2004-10-07 Kpss-Kao Professional Salon Services Gmbh Use of a hair treatment product
WO2005102253A1 (en) * 2004-04-26 2005-11-03 Henkel Kommanditgesellschaft Auf Aktien Hair dye agent comprising organosilicon copolymers with amino groups and polyoxyalkylene groups and use thereof
US7981687B2 (en) * 2004-03-30 2011-07-19 Sakura Color Products Corporation Ink composition for sensing gas exposure and gas exposure indicator
US20160141192A1 (en) 2013-08-22 2016-05-19 Sakura Color Products Corporation Indicator used in electronic device manufacturing apparatus and method for designing and/or managing the apparatus
FR3045346A1 (en) * 2015-12-21 2017-06-23 Oreal COLORING COMPOSITION COMPRISING A DIRECT COLOR OF TRIARYLMETHANE STRUCTURE AND SILICONE
US10180413B2 (en) 2014-12-02 2019-01-15 Sakura Color Products Corporation Ink composition for plasma processing detection, and indicator for plasma processing detection using said ink composition
US10180392B2 (en) 2014-05-09 2019-01-15 Sakura Color Products Corporation Plasma processing detection indicator using inorganic substance as a color-change layer
US10184058B2 (en) 2014-04-21 2019-01-22 Sakura Color Products Corporation Ink composition for detecting plasma treatment and indicator for detecting plasma treatment
US10401338B2 (en) 2014-02-14 2019-09-03 Sakura Color Products Corporation Plasma processing detection indicator
US10400125B2 (en) 2014-09-16 2019-09-03 Sakura Color Products Corporation Ink composition for plasma treatment detection, and plasma treatment detection indicator
US11000464B2 (en) 2015-12-21 2021-05-11 L'oreal Dyeing composition at acidic pH comprising a direct dye of triarylmethane structure

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2110722A (en) * 1981-12-02 1983-06-22 Oreal Use of benzoquinones for the direct dyeing of keratin fibres
GB2110723A (en) * 1981-12-02 1983-06-22 Oreal Use of hydroxynaphthoquinones for dyeing human keratin fibres
GB2129022A (en) * 1982-01-26 1984-05-10 Oreal Hair dyeing compositions containing 1-(substituted phenoxy)-3-amino-propan-2-ol compounds
GB2132643A (en) * 1982-12-08 1984-07-11 Oreal Use of 5-hydroxynaphthoquinones for dyeing human keratin fibres
GB2135329A (en) * 1983-01-28 1984-08-30 Schwarzkopf Gmbh Hans Substituted 4-amino-3-nitrophenols processes for their preparation and hair-colouring agents containing them
GB2142348A (en) * 1983-06-27 1985-01-16 Oreal Dyeing compositions for keratin fibres, based on direct dyestuffs and xanthan gums

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2110722A (en) * 1981-12-02 1983-06-22 Oreal Use of benzoquinones for the direct dyeing of keratin fibres
GB2110723A (en) * 1981-12-02 1983-06-22 Oreal Use of hydroxynaphthoquinones for dyeing human keratin fibres
GB2129022A (en) * 1982-01-26 1984-05-10 Oreal Hair dyeing compositions containing 1-(substituted phenoxy)-3-amino-propan-2-ol compounds
GB2132643A (en) * 1982-12-08 1984-07-11 Oreal Use of 5-hydroxynaphthoquinones for dyeing human keratin fibres
GB2135329A (en) * 1983-01-28 1984-08-30 Schwarzkopf Gmbh Hans Substituted 4-amino-3-nitrophenols processes for their preparation and hair-colouring agents containing them
GB2142348A (en) * 1983-06-27 1985-01-16 Oreal Dyeing compositions for keratin fibres, based on direct dyestuffs and xanthan gums

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4943430A (en) * 1986-07-30 1990-07-24 Lever Brothers Company Treatment of keratinous fibres
EP0312343A3 (en) * 1987-10-15 1989-07-12 Unilever Plc Hair treatment product
US4964874A (en) * 1987-10-15 1990-10-23 Unilever Patent Holdings B.V. Hair treatment product
EP0312343A2 (en) * 1987-10-15 1989-04-19 Unilever Plc Hair treatment product
JPH078778B2 (en) * 1990-04-10 1995-02-01 ホーユー株式会社 Hair dye
JPH03294217A (en) * 1990-04-10 1991-12-25 Hoyu Co Ltd Hair dye
EP0589656A2 (en) * 1992-09-21 1994-03-30 Dow Corning Corporation Method of coloring hair with water soluble acid dyes
EP0589656A3 (en) * 1992-09-21 1994-10-12 Dow Corning Method of coloring hair with water soluble acid dyes.
US5281240A (en) * 1992-09-21 1994-01-25 Dow Corning Corporation Method of coloring hair with water soluble acid dyes
FR2713927A1 (en) * 1993-12-22 1995-06-23 Oreal Process for the direct dyeing of human keratin fibers using water vapor
EP0659399A1 (en) * 1993-12-22 1995-06-28 L'oreal Process of direct hair using steam
US5496377A (en) * 1993-12-22 1996-03-05 L'oreal Process for the direct dyeing of keratinous fibres using water vapor
US5711765A (en) * 1994-09-21 1998-01-27 L'oreal Process for the direct dyeing of human keratin fibres using cationic dyes and water vapor
FR2724560A1 (en) * 1994-09-21 1996-03-22 Oreal PROCESS FOR DIRECT COLORING OF KERATIN FIBERS USING CATIONIC DIRECT DYES AND WATER VAPOR
EP0705597A1 (en) * 1994-09-21 1996-04-10 L'oreal Process of direct hair dyeing using cationic direct dyes and steam
EP0756861A3 (en) * 1995-07-31 1999-06-16 Kao Corporation Composition for dyeing of human hair
EP0756861A2 (en) * 1995-07-31 1997-02-05 Kao Corporation Composition for dyeing of human hair
JPH09100223A (en) * 1995-07-31 1997-04-15 Kao Corp Hair dye composition
WO1999011227A1 (en) * 1997-09-04 1999-03-11 Cognis Deutschland Gmbh Use of ester quaternaries as emulsifiers for producing preparations for coloring keratin fibers
AU744100B2 (en) * 1997-09-04 2002-02-14 Cognis Deutschland Gmbh Use of ester quaternaries as emulsifiers for producing preparations for coloring keratin fibers
DE19758272C5 (en) * 1997-12-31 2004-10-07 Kpss-Kao Professional Salon Services Gmbh Use of a hair treatment product
US7507260B2 (en) 1998-08-26 2009-03-24 L'oreal S.A. Composition for dyeing keratinous fibres with a cationic direct dye and a silicone
WO2000012057A1 (en) * 1998-08-26 2000-03-09 L'oreal Dyeing composition for keratinous fibres with a cationic direct colouring agent and a silicone
FR2783416A1 (en) * 1998-08-26 2000-03-24 Oreal DYEING COMPOSITION FOR KERATINIC FIBERS WITH DIRECT CATIONIC COLOR AND SILICONE
AU728730B2 (en) * 1998-08-26 2001-01-18 L'oreal Composition for dyeing keratinous fibres with a cationic direct dye and a silicone
US7981687B2 (en) * 2004-03-30 2011-07-19 Sakura Color Products Corporation Ink composition for sensing gas exposure and gas exposure indicator
WO2005102253A1 (en) * 2004-04-26 2005-11-03 Henkel Kommanditgesellschaft Auf Aktien Hair dye agent comprising organosilicon copolymers with amino groups and polyoxyalkylene groups and use thereof
US20160141192A1 (en) 2013-08-22 2016-05-19 Sakura Color Products Corporation Indicator used in electronic device manufacturing apparatus and method for designing and/or managing the apparatus
US10181414B2 (en) 2013-08-22 2019-01-15 Sakura Color Products Corporation Indicator used in electronic device manufacturing apparatus and method for designing and/or managing the apparatus
US10401338B2 (en) 2014-02-14 2019-09-03 Sakura Color Products Corporation Plasma processing detection indicator
US10184058B2 (en) 2014-04-21 2019-01-22 Sakura Color Products Corporation Ink composition for detecting plasma treatment and indicator for detecting plasma treatment
US10180392B2 (en) 2014-05-09 2019-01-15 Sakura Color Products Corporation Plasma processing detection indicator using inorganic substance as a color-change layer
US10400125B2 (en) 2014-09-16 2019-09-03 Sakura Color Products Corporation Ink composition for plasma treatment detection, and plasma treatment detection indicator
US10180413B2 (en) 2014-12-02 2019-01-15 Sakura Color Products Corporation Ink composition for plasma processing detection, and indicator for plasma processing detection using said ink composition
FR3045346A1 (en) * 2015-12-21 2017-06-23 Oreal COLORING COMPOSITION COMPRISING A DIRECT COLOR OF TRIARYLMETHANE STRUCTURE AND SILICONE
WO2017108828A1 (en) * 2015-12-21 2017-06-29 L'oreal Dyeing composition comprising a direct dye of triarylmethane structure, and a silicone
US11000464B2 (en) 2015-12-21 2021-05-11 L'oreal Dyeing composition at acidic pH comprising a direct dye of triarylmethane structure
US11007131B2 (en) 2015-12-21 2021-05-18 L'oreal Dyeing composition comprising a direct dye of triarylmethane structure, and a silicone

Also Published As

Publication number Publication date
GB2168082B (en) 1988-09-14
GB8517349D0 (en) 1985-08-14

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Legal Events

Date Code Title Description
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19920709