GB2138845A - Deep colouration of hair - Google Patents
Deep colouration of hair Download PDFInfo
- Publication number
- GB2138845A GB2138845A GB08404625A GB8404625A GB2138845A GB 2138845 A GB2138845 A GB 2138845A GB 08404625 A GB08404625 A GB 08404625A GB 8404625 A GB8404625 A GB 8404625A GB 2138845 A GB2138845 A GB 2138845A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hair
- dye
- dyes
- carbon atoms
- alkyl
- 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
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
- A61K8/84—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
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes 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
Abstract
Hair dye compositions comprising an amino-modified silicone derivative represented by the following formula (I> <IMAGE> in which R: an alkyl group having 1-4 carbon atoms or an aryl group, R1, R2, R3: an alkyl or alkoxy group having 1-2 carbon atoms, R4: (a> <IMAGE> or (b> <IMAGE> X: Cl, Br or I, m: an integer of 0-100, and n: an integer of 1-50. A composition according to the invention can dye hair to give deeper tone than known compositions, without impeding agreeable touch of the hair.
Description
SPECIFICATION
Hair dye compositions
BACKGROUND OF THE INVENTION i) Field of the Invention:
This invention relates to hair dye compositions and more particularly, to hair dye compositions which comprise a specific type of silicone derivative by which the hair can be dyed in deep color.
ii) Description of the Prior Art:
Hair dyes are broadly classified into two categories, one being a so-called "grey hair dye" which is used to have a grey hair dyed black or brown, the other being a "hair color" which is used to have a black hair dyed bright brown or the like. In either case, these dyes or colors are used for the purpose of beauty care. These hair dyes are required to cover therewith, without failure, the site of the hair to be dyed and to finish the hair without breaking harmony as a whole. However, existing hair dyes are disadvantageous in that (1) dyes or pigments which are used as dyeing substrate are different in nature from the colorant component (melanine) in the hair itself, and (2) contents of dyes or pigments in dye composition are so small that the hair has not been dyed deeply in color.This leads to low covering and dyeing powers, with the attendant disadvantage that the hair cannot be dyed in natural tone, thus being objectionable.
In order to overcome the disadvantages, there is known a method in which a content of concentration of dye or pigment in hair dye is increased. For instance, with regard to oxidation hair dyes, there appear a number of reports in succession presenting some doubts on harmlessness of oxidation dyes and couplers contained therein. In advanced countries, use of an increasing number of oxidation dyes or couplers is regulated. Under these circumstances, it is not favorable to use these substances by increasing their concentrations.
Temporary hair dyes are also known. Such hair dyes are disadvantageous in that where dyes or pigments are dispersed in a dispersion medium such as an alcohol or water in high concentrations, the resulting dispersion tends to suffer a phase separation, thus it being difficult to stably keep such a product over a long term. Moreover, high concentrations of dyes or pigments in hair dye need larger amounts of polymer resins, vehicles and the like in order to prevent the dye or pigment from falling off after dyeing. This will render once dyed hair stiff of hard and impede smooth combing or brushing of the hair, thus causing poor feeling of the hair to the touch and damages of the hair.
SUMMARY OF THE INVENTION
We made intensive studies on hair dyes which have excellent covering and dyeing powers without increasing a dye or pigment concentration in composition and which can impart deep color tone to the hair after dyeing. As a result, it was found that hair dye compositions which comprise a specific type of silicone derivative overcome the prior art disadvantages.
That is, the present invention provides hair dye compositions comprising a specific type of silicone derivative.
The silicone derivatives used in the practice of the invention are represented by the following formula (I)
in which R: an alkyl group having 1-4 carbon atoms or an aryl group,
R,: an alkyl group or alkoxy group having 1-2 carbon atoms, R2: an alkyl or alkoxy group having 1-2 carbon atoms,
R3: an alkyl or alkoxy group having 1-2 carbon atoms, R4 (a)
in which R5 and R7 independently represent an alkyl or hydroxyalkyl group having 1-3 carbon atoms, and R6 represents the same group as R5,
or -CH2CH = CH2,
X: CI,Br or I, m: an integer of 0-100, and n: an integer of 1.50.
The silicone derivatives indicated above may be used singly or in combination.
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS
The silicone derivatives (I) are prepared by any known methods, for example, a method disclosed in United State Patent No. 3389160.
The amount of the silicone derivatives in a hair dye composition is generally in the range of from 0.1 to 10 wt% (hereinafter referred to simply as "%"), preferably from 0.2 to 5%, and most preferably from 0.5 to 3%. Amounts less then 0.1% are unfavorable because the hair cannot be dyed deeply, whereas larger amounts more than 10% involve the problem that the dyed hair does not dry soon and is sticky, and is thus felt desagreeable to the touch.
The hair dye composition of the present invention may take any forms of a so-called permanent hair dye of the oxidation type and a so-called permanent, semi-peremanent or temporary hair dye or hair color of the non-oxidation type. Aside from silicone derivatives, any known hair dye substrates or ingredients may be added to the hair dye of the invention, which may vary depending on the form or type of hair dye.
(1) Oxidation-type Hair Dyes
The oxidation-type hair dye is a hair dye in which a dye intermediate is oxidized with an oxidizing agent to form a coloring matter or pigment with which the hair is dyed. Couplers or modifiers do not produce any coloring matter when oxidized singly, but form a coloring matter when oxidized singly, but form a coloring matter when oxidized in the presence of a dye intermediate. Accordingly, the hair dye substrate of the oxidation type comprises dye intermediates, oxidizing agents, and reactive componds serving as a coupler or modifier used in combination, if necessary.The dye intermediates include, for example, para and ortho compounds such as p-phenylenediamine, toluene-2,5-diamine, N-phenyl-p-phenyldiamine, 4,4'diaminodiphenylamine, p-aminophenol, p-methylaminophenol, o-phenylenediamine, toluene-3,4diamine, o-aminophenol, p-chloro-o-phenylenediamine, p-amino-o-cresol, o-chloro-p-phenylenediamine, phloroglucin, pyrogallol, 3,3'-iminodiphenyl, diphenylamine, 2,6-diaminopyridine, paminophenylsulfamic acid, and the like. Couplers or modifiers include, for example, meta compounds and phenols such as m-phenylenediamine, toluene-2,4-diamine, p-methoxy-mphenylenediamine, m-aminophenol, alphanaphthol, resorcine, hydroquinone, catechol, and the like.Oxidizing agents are, for example, hydrogen peroxide, sodium perborate, urea peroxide, sodium percarbonate, sodium peroxytripoiyphosphate, sodium peroxypyrophosphate, sodium peroxy-o-phosphate, sodium silicate and hydrogen peroxide adduct, sodium sulfate, sodium chloride and hydrogen peroxide adduct, and the like. The oxidation-type hair dye substrate may further comprise, aside from the above-indicated ingredients, dyes which do not take part in the coloring matter-formation reaction but give an influence on the color of the hair in order to keep the quality of the hair dye product and increase the utility thereof. Examples of the dyes include nitro dyes such as nitro-p-phenylenediamine, p-n itro-o-phenylenediamine, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 4-amino-2-nitrophenol and the like, and direct dyes such as picramic acid, picric acid, 1 ,4-diaminoanthraquinone and the like.Moreover, there may be added to the hair dye substrate the following ingredients: surface active agents such as nonionic active agents, anionic active agents, amphoteric active agents and cationic active agents; solubilizers such as propylene glycol, glycerine, urea and the like; lower alcohols such as ethyl alcohol, isopropyl alcohol and the like; viscosity modifiers such as hydroxyethyl cellulose, methyl cellulose, cationic polymer compounds, higher alcohols and the like; pH adjusters used to adjust a dye solution to a pH range of from 7 to 11, preferably from 8 to 10 at which a hair dyeing treatment is effected; and colorants, UV absorbers, antioxidants, preservative, pearling agents, lotionizing agents, stabilizers, osmotic agents, humectants, hair tonics, perfumes vaseline, solvents such as liquid paraffin, and the like substances.
The oxidation-type hair dye may be used in the form of one component preparation which is obtained by mixing a oxidation-type hair dye substrate and at least one silicone derivative as usual to give a powder or cream preparation. In practically applications, water or a shampoo substrate is added to the powder or cream preparation. Alternatively, a dye intermediate and an oxidizing agent may be separately formed into a powder, cream or liquid preparation. The separate preparations are mixed together when used. Still alternatively, the hair dye may be used as one-component preparation to which are added pyrogallol and a ferrous salt.
(2) Permanent or semi-permanent hair dyes of the non-oxidation type.
Typical of the non-oxidation-type permanent or semi-permanent hair dyes are plant hair dyes and metallic hair dyes. The plant hair dyes make use of extracts from henna, walnut and soybean as a substrate. The colorant ingredients in the extract have the function to dye hair keratin. In the metallic hair dye, chemical reactions of metals of which insoluble metal salts are produced are utilized. Metals used as a substrate include iron, copper, lead, manganese, nickel, cadmium and the like, of which iron is preferred.
Apart from the hair dye substrates and silicone derivatives, the non-oxidation-type permanent of semi-permanent hair dyes may further comprise any known ingredients indicated in (1). The hair dyes may take any preparation forms as in (1).
(3) Temporary hair dyes of the non-oxidation type
The temporary hair dyes are used to dye the hair by adsorbing a hair dye substrate such as an oxidation dye or pigment directly on the hair or by covering the hair with a resin containing such substrate. Dyes or pigments used as the substrate are not limited to any specific ones and include, for example, pigments such as titanium oxide, carbon black and the like, and tar colorants such as triphenylmethane, dyes, azo dyes, quinoline dyes, xanthese dyes, acridine dyes, azine dyes, oxazine dyes, indigoid dyes, anthraquinone dyes, stilbene dyes, thiazole dyes and the like.
The resins used in the substrate are, for example, copolymers of acrylic esters, methacrylic esters and the like, copolymers of monochloroacetic acid-amine salt modified products of N,N'dimethylaminoethyl methacrylate and methacrylic esters, copolymers of vinyl pyrrolidone and vinyl acetate, and the like.
The temporary hair dyes may also contain, aside from the substrate and silicone derivatives, any known ingredients including: dispersion media, serving to dissolve or disperse the substrate and silicone derivatives, such as water, amyl alcohol, isopropanol, ethanol, acetone and the like; surface active agents such as anionic active agents, cationic active agents, amphoteric active agents and non ionic active agents; polyhydric alcohols such as propylene glycol, glycerine, polyethylene glycol and the like; higher alcohols such as isostearyl alcohol, oleyl alcohol and the like; fatty acids such as lanolin fatty acids, coconut fatty acids and the like; esters such as isopropyl myristate; hydrocarbons such as liquid paraffin; and cationic polymer compounds, amines and perfumes.
The temporary hair dye is obtained by dissolving or dispersing solid ingredients in a dispersion medium and may take various forms such as mascara, spray, lotion and the like.
The amounts of the respective constituents of the temporary hair dye are not critical. Typical compositions are shown below.
(1) Mascara type
Pigment and/or dye 0.5-5%
Polymer resin 5-20%
Silicone derivative 0.2-5%
Water and/or ethanol balance (2) Spray type
Pigment and/or dye 0.1-3% Polymer resin 1-10% Silicone derivative 0. 1-3% Water and/or ethanol balance
Flon gas (mixed gas of 40% of Flon 11 and 60%
of Flon 12) 40-70% (3) Lotion type
Dye 0.1-1%
Humectant 2-30%
Silicone derivative 0.1-3% Dispersion medium balance
(pH is adjusted to 1-5 by the use of
phosphoric acid, citric acid or the like.)
The hair dye compositions of the present invention are deeper in color than known counterparts and do no impede agreeable touch of the hair when applied thereto.
The present invention is described by way of synthetic example and examples, which should not be construed as limiting the present invention thereto.
Synthetic Example
An amino-modified silicone derivative represented by the following formula (la)
was prepared according to the following reaction formula.
[First Step]
220 g (0.3 mole) of compound (11), 37.1 g (0.33 mole) of compound (Ill) and 39 mg of an propyl alcohol solution of 10% (w/w) H2PtCI66H2O (9 X 10-6 mole as H2PtCI6) were placed in 300 ml distillation flask and gradually heated, followed by reaction at 1 1 0 C for 4 hours. After completion of the reaction, the reaction system was heated under reduced pressure to remove unreacted compound (III) therefrom. The platinum catalyst was removed as follows: active carbon was added to the reaction mixture, sufficiently shaked and filtered. The resultant reaction product was subjected to IR, NMR and the like analyses and identified as compound (IV). The compound was obtained in an amount of 1 53 g in a yield of 60%.
[Second Step]
85 g (0.10 mole) of compound (IV) and 100 g of ethanol were placed in a 300 ml distillation flask and heated to 70"C. Subsequently, 15 g (0.21 mole) of HN (C2H5)2 was gradually added to the mixture, followed by refluxing for 2 hours. After completion of the reaction, the ethanol and unreacted HN (C2Hs)2 were distilled off under a reduced pressure (0.3 mmHg, 40"C). The reaction product was subjected to IR, NMR and the like analyses and identified as compound (la). This compound was obtained in an amount of 89 g in a yield of 97%.
Example 1
An oxidation-type permanent hair dye of the following formulation was prepared and used to dye the hair therewith. The color of the dyed hair was evaluated. The results are shown in
Tables 1 and 2. Formulation.
(First lotion)
p-Phenylenediamine 1.0%
Propylene glycol 10.0
Sodium edetoate 0.3
Sodium sulfite 0.5
Perfume 0.1
Additive (Table 1) 1.0
Polyoxyethylene (6) stearyl ether 1.0
Water balance
(pH was adjusted to 10.0 by the use of
ammoniacal solution.)
Second lotion)
Hydrogen peroxide 6.0%
Water 94.0
Procedure for Hair Dyeing Treatment:
In a mixture of the first and second lotion in equal amounts was immersed the hair for 30 minutes. The dyed hair was sufficiently washed with a 1% sodium dodecylsulfate aqueous solution and then with running water, and air-dried.
Evaluation:
(1) Colorimetry
The colorimeter and color difference computer ND-1010C (made by Nippon Denshoku Ind.
Co., Ltd.) was used to measure a lightness of the dyed hair. The lightness is indicated as an L value in Table 1 and a smaller value shows a deeper color.
(2) Visual Evaluation
Twenty female panelers effected a paired comparison between a hair dyed with the hair dye
No. 1 of the invention and a hair dyed with a comparative dye No. 4 or 5, thereby evaluating the hairs dyed black with respect to their depth in color. The results are shown in Table 2.
Composi- Lightness tion No. Additives (L value)
Hair Dyes of the Invention 1 Amino-modified silicone derivative (la)
in formula (I), R, R1, R2 and
R3: CH3, R4: structure (b) in 13.0
which R, = C2Hs, m 3, and n = 1.5
(prepared in the same manner as in
Synthetic Example) 2 Amino-modified silicone derivative (lib) in formula (I), R, R1, R2 and
R3: CH3, R4: structure (a) in 13.1
which R5 = CH3, m = 28, and n = 8
(prepared in the same manner as in
Synthetic Example) 3 Amino-modified silicone derivative (Ic)
in formula (I), R: CH3, R1, R2
and R3:OCH3, R4: structure (b) in 13.1
which R7 = C2H4OH, m = 30, and n = 8
(prepared in the same manner as in
Synthetic Example)
Comparative Hair Dyes 4 Amino-modified silicone
(DC536 by Toray Industries, Inc.) 14.0 5 Isopropyl methacrylate 1 5.5 6 Butyl acrylate 15.4 7 Isobutyl methacrylate 1 5.4 Control 8 Nil 15.5
Table 2
Comparison Comparison
between the dye between the dye
Evaluation No. 1 of the No. 1 of the
invention and invention and
the comparative the comparative
dye No. 4 dye No. 5
The inventive dye 11 persons 1 8 persons felt deeper
The inventive dye felt slightly deeper 6 2
No difference 3 0
The comparative dye felt slightly deeper 0 0
The comparative dye felt deepter 0 0
Example 2
Hair dyes of the following formulations were prepared.These dyes were found to be excellent in color depth when applied to the hair.
(1) Spray hair dye (temporary hair dye)
Polymer resin (Plascize L) 1.8%
Carbon black 0.3
Amino-modified silicone derivative 0.5
[compound (Ic) in Table 1]
Ethanol 37.4
Flon gas (11/12:40/60) 60 (2) Quick braking foam-type hair dye
Polymer resin (Plascize L) 1.8%
Carbon black 0.3
Amino-modified silicone derivative 0.8
[compound (Ib) in Table 1]
Self-emulsifying wax composed of
80%n of cetostearyl alcohol and 20% 1.5
of polyethylene glycol (1000)
monostearate
Ethanol 30.6
Polyoxyethylene glycol 5.0
Flon gas (11/12: :40/60 60 (3) Lotion-type hair dye (temporary hair dye) using an oxidation dye
Black 401 0.5%
(Sodium 8-amino-7-para-nitrophenylazo 2-phenylazo-1 -naphthol-3,6-disulfonate) Amino-modified
silicone derivative 1.0
[compound (1a) in Table 1]
Polyoxyethlene stearyl ether 1.0
Ethanol 3.0
Water balance
(pH was adjusted to 2.0-3.0 by means
of citric acid.)
Claims (3)
1. A hair dye composition characterized by comprising one or more amino-modified silicone derivatives represented by the following formula (I)
in which R: an alkyl group having 1-4 carbon atoms or an aryl group,
R,: an alkyl or alkoxy group having 1-2 carbon atoms,
R2: an alkyl or alkoxy group having 1-2 carbon atoms,
R3: an alkyl or alkoxy group having 1-2 carbon atoms, R4: (a)
in which R5 and R7 independently represent an alkyl or hydroxyalkyl group having 1-3 carbon atoms, and R6 represents the same group as R5,
or -CH2CH = CH2,
X: CI, Br or I, m: an integer of 0-100, and n: an integer of 1.50.
2. A hair dye composition as claimed in claim 1 and substantially as described in any one of the specific examples hereinbefore set forth.
3. Each and every novel embodiment herein set forth either separately or in combination.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6346783A JPS59190910A (en) | 1983-04-11 | 1983-04-11 | Hair dye composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8404625D0 GB8404625D0 (en) | 1984-03-28 |
| GB2138845A true GB2138845A (en) | 1984-10-31 |
| GB2138845B GB2138845B (en) | 1986-03-19 |
Family
ID=13230068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08404625A Expired GB2138845B (en) | 1983-04-11 | 1984-02-22 | Deep colouration of hair |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS59190910A (en) |
| AT (1) | AT393450B (en) |
| CH (1) | CH658384A5 (en) |
| DE (1) | DE3413125A1 (en) |
| GB (1) | GB2138845B (en) |
| HK (1) | HK43990A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2186889A (en) * | 1986-02-26 | 1987-08-26 | Dow Corning | Colouring keratinous material |
| GB2205111A (en) * | 1987-05-25 | 1988-11-30 | Oreal | Dyeing keratinous fibres with couplers and/or "rapid" oxidation dyes together with iodide ions |
| US4898595A (en) * | 1986-02-26 | 1990-02-06 | Dow Corning Limited | Coloring keratinous material |
| US4943430A (en) * | 1986-07-30 | 1990-07-24 | Lever Brothers Company | Treatment of keratinous fibres |
| US4985166A (en) * | 1987-12-18 | 1991-01-15 | Rhone-Poulenc Chimie | Magnetizable composite particles based on cross-linked organopolysiloxane, process for preparation thereof and their application in biology |
| US5281240A (en) * | 1992-09-21 | 1994-01-25 | Dow Corning Corporation | Method of coloring hair with water soluble acid dyes |
| US6432145B1 (en) | 2000-12-26 | 2002-08-13 | Dow Corning Corporation | Oxidation hair dyeing agent composition |
| DE10304923A1 (en) * | 2003-02-07 | 2004-08-26 | Ge Bayer Silicones Gmbh & Co. Kg | Use of linear or branched polyamino- and-or polyammonium-polysiloxane copolymers in the production and-or treatment of dyed hair, e.g. in shampoos, rinses, styling gels, hair sprays and conditioners |
| EP1543820A1 (en) * | 2003-12-18 | 2005-06-22 | The Procter & Gamble Company | Enhancing the colour perception of artificially coloured hair |
| 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 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0474113A (en) * | 1990-07-13 | 1992-03-09 | Kao Corp | Hair-dye composition |
| TW199103B (en) * | 1991-02-15 | 1993-02-01 | Shiseido Co Ltd | |
| JPH05194161A (en) * | 1991-08-20 | 1993-08-03 | Shiseido Co Ltd | Acidic hair dyeing agent composition for hair |
| DE4443062C2 (en) * | 1994-12-03 | 1997-07-17 | Wella Ag | Means and methods for permanent hair deformation |
| KR20040007097A (en) * | 2002-07-16 | 2004-01-24 | 주식회사 엘지생활건강 | Hair dye and post treatment composition |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1585308A (en) * | 1967-10-10 | 1970-01-16 | ||
| JPS49117492U (en) * | 1973-02-06 | 1974-10-07 | ||
| GB1524683A (en) * | 1974-12-20 | 1978-09-13 | Bicc Ltd | Termination of electric cables |
| US4096243A (en) * | 1976-02-09 | 1978-06-20 | Clairol Incorporated | Composition for lightening hair containing an oxidizing agent and certain quaternary amines |
| FR2443476A1 (en) * | 1978-12-05 | 1980-07-04 | Oreal | NOVEL SURFACTANT POLYSILOXANES, PROCESS FOR PREPARING SAME AND COMPOSITIONS CONTAINING THE SAME |
| JPS57192310A (en) * | 1981-05-20 | 1982-11-26 | Kao Corp | Hair dyeing agent composition |
-
1983
- 1983-04-11 JP JP6346783A patent/JPS59190910A/en active Granted
-
1984
- 1984-02-22 GB GB08404625A patent/GB2138845B/en not_active Expired
- 1984-03-20 AT AT94084A patent/AT393450B/en not_active IP Right Cessation
- 1984-03-28 CH CH156484A patent/CH658384A5/en not_active IP Right Cessation
- 1984-04-06 DE DE19843413125 patent/DE3413125A1/en not_active Ceased
-
1990
- 1990-06-07 HK HK43990A patent/HK43990A/en unknown
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4898595A (en) * | 1986-02-26 | 1990-02-06 | Dow Corning Limited | Coloring keratinous material |
| GB2186889A (en) * | 1986-02-26 | 1987-08-26 | Dow Corning | Colouring keratinous material |
| US4943430A (en) * | 1986-07-30 | 1990-07-24 | Lever Brothers Company | Treatment of keratinous fibres |
| GB2205329B (en) * | 1987-05-25 | 1992-01-02 | Oreal | Process for dyeing keratinous fibres with oxidation bases combined with an iodide and dyeing composition employed |
| GB2205329A (en) * | 1987-05-25 | 1988-12-07 | Oreal | Dyeing keratinous fibres with oxidation dyes together with iodide ions |
| US4985955A (en) * | 1987-05-25 | 1991-01-22 | L'oreal | Process for dyeing keratinous fibres with couplers and/or "rapid" oxidation dyes combined with an iodide and dyeing composition employed |
| GB2205111B (en) * | 1987-05-25 | 1992-01-02 | Oreal | Upatentsfor dyeing keratinous fibres with couplers and/or "rapid" oxidation dyes combined with an iodide and dyeing composition employed |
| GB2205111A (en) * | 1987-05-25 | 1988-11-30 | Oreal | Dyeing keratinous fibres with couplers and/or "rapid" oxidation dyes together with iodide ions |
| US4985166A (en) * | 1987-12-18 | 1991-01-15 | Rhone-Poulenc Chimie | Magnetizable composite particles based on cross-linked organopolysiloxane, process for preparation thereof and their application in biology |
| US5281240A (en) * | 1992-09-21 | 1994-01-25 | Dow Corning Corporation | Method of coloring hair with water soluble acid dyes |
| 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 |
| US6432145B1 (en) | 2000-12-26 | 2002-08-13 | Dow Corning Corporation | Oxidation hair dyeing agent composition |
| DE10304923A1 (en) * | 2003-02-07 | 2004-08-26 | Ge Bayer Silicones Gmbh & Co. Kg | Use of linear or branched polyamino- and-or polyammonium-polysiloxane copolymers in the production and-or treatment of dyed hair, e.g. in shampoos, rinses, styling gels, hair sprays and conditioners |
| EP1543820A1 (en) * | 2003-12-18 | 2005-06-22 | The Procter & Gamble Company | Enhancing the colour perception of artificially coloured hair |
| WO2005063180A1 (en) * | 2003-12-18 | 2005-07-14 | The Procter & Gamble Company | Enhancing the colour perception of artifically coloured hair |
| US7335236B2 (en) | 2003-12-18 | 2008-02-26 | The Procter & Gamble Company | Enhancing the colour perception of artificially coloured hair |
Also Published As
| Publication number | Publication date |
|---|---|
| HK43990A (en) | 1990-06-15 |
| GB8404625D0 (en) | 1984-03-28 |
| DE3413125A1 (en) | 1984-10-11 |
| JPH0363528B2 (en) | 1991-10-01 |
| JPS59190910A (en) | 1984-10-29 |
| CH658384A5 (en) | 1986-11-14 |
| GB2138845B (en) | 1986-03-19 |
| ATA94084A (en) | 1991-04-15 |
| AT393450B (en) | 1991-10-25 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19960222 |