US3630655A - Dyeing human hair with oxidation dyes comprising heterocyclic amino compounds - Google Patents
Dyeing human hair with oxidation dyes comprising heterocyclic amino compounds Download PDFInfo
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- US3630655A US3630655A US769749A US3630655DA US3630655A US 3630655 A US3630655 A US 3630655A US 769749 A US769749 A US 769749A US 3630655D A US3630655D A US 3630655DA US 3630655 A US3630655 A US 3630655A
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- methyl
- amino
- hair
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- heterocyclic amino
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
Abstract
The novel means for dyeing human hair according to the invention are based on oxidation dyes and comprise heterocyclic amino compounds and suitable coupling components. For example, 2 parts of 6-aminotetrahydroquinoline hydrochloride, 1 part of Alpha naphthol, 1 part of hydrogen peroxide are mixed with 96 parts of water and adjusted to a pH of 9.5. By treating gray human hair with the resulting solution a dark blue coloration is obtained. The hair dyes according to the invention have, in addition to other favorable characteristics, the advantage of being easily removable from the hair, e.g., by reducing agents.
Description
O United States Patent 11 [72] Inventors Peter Berth [56] References Cited g z g g m m we UNITED STATES PATENTS u o au as e 0 many pp No. 769,749 2,196,739 4/l940 Peterson 96/100 X [22] Filed Oct. 22, 1968 Primary ExaminerAlbert T. Meyers [45] Patented Dec. 28, 1971 Assistant Examiner-Vera C. Clarke [73]- Assignee Theraehemle Chemlsch 'l'herapeutlsche Attorney-l-lammond & Littell Gesellschaft m.b.l-l. [32] Priority Nov. 6, 1967 [33] Austria [311 A 9977/67 ABSTRACT: The novel means for dyeing human hair according to the invention are based on oxidation dyes and comprise [54] DYES heterocyclic amino compounds and suitable coupling com- COMPOUNDS ponents. For example, 2 parts of G-aminotetrahydroquinoline 5 Claims No Draw 5 hydrochloride, 1 part of a-naphthol, 1 part of hydrogen peroxg ide are mixed with 96 parts of water and adjusted to a pH of [52] US. Cl 8/11, 9.5. By treating gray human hair with the resulting solution a l 8/ 10.2 dark blue coloration is obtained. [51] Int. Cl A61]: 7/12, The hair dyes according to the invention have, in addition to D06p 1/32 other favorable characteristics, the advantage of being easily [50] Field of Search 8/102, 11, removable from the hair, e.g., by reducing agents.
DYEING HUMANHATRWITH OXIDATION DYES COMPRISINGHETEROCYCLIC AMINO COMPOUNDS This invention relates to'agentsfor dyeing human hair by means of'oxidation dyes, particularly by means of heterocyclic amino compounds.
it has been known to use for dyeing human hair oxidation dyes which contain as the dye component phenylene diamines. It has also been suggested to use for these purposes diaminopyridines. The before-mentioned compounds are converted by oxidation with-atmospheric oxygen, or especially by the addition of chemical oxidizing agents, such as hydrogen lI N X stands for the atoms necessary for the formation of a heterocyclic, nonaromatic, five-membered ring, or six-membered ring; as well as b. coupling components known by themselves for hair dyes, on the basis of aromatic compounds containing amino groups or hydroxyl groups, or hydroxyl and amino groups, or pyrazolones, or aroyl derivatives, or acylacetic acid derivatives.
in carrying out the invention, it is preferred to use compounds, in which in the heterocyclic amino compound correspondingto the formula (I), the radical or group R, is an aliphatic'radical having-not more than 10 carbon atoms, especially an alkyl group or a hydroxy-alkyl group having in each case one-four carbon atoms. Said alkyl group may be rectilinear or branched.
Substitutents of the first orderdescribed above for the symbol R of the heterocyclic amino compounds of the formula (l)are, for example, the following: halogen atoms, especially chlorine or bromine atoms, rectilinear or branched alkyl groups containing one-four carbon atoms, substituted alkyl groups of said chain length, such as, for example, hydroxyalkyl groups or aminoalkyl groups, and also amino groups, amino groups substituted by alkyl radicals or alkanol radicals and also hydroxyl groups substituted by alkyl groups, such as --OCH or -C 'l-l The formation of a heterocyclic, nonaromatic five-membered ring or six-membered ring, can be brought about in different ways. According to a preferred embodiment, heterocyclic amino compounds'corresponding to the above formula (I) can be used in which X stands for one of the groups aminoindolenine; (Cl-lphd 2) CH,-CH-,, --CH CH(CH '-NR-CH,'-CH,-, -Cl-l,NR--CH O-CH,CH,; (R being Hor an alkyl group having one to four carbon atoms). Further examples are amino compounds corresponding to the formula (I) in which X stands for the group CONH'- or NHCOCH As individual compounds, especially the following can be considered: 6- aminotetrahydroquinoline; l-methyl-6-aminotetrahydroquinoline; 1-methyl-6,8-diaminotetrahydroquinoline; l-methyl-6- amino-8-methoxytetrahydroquinoline; l-ethyl-6- aminotetrahydroquinoline; l-(B-hydroxyethyl)-6- aminotetrahydroquinoline; 4-methyl-7-aminodihydrobenzoxazine [,4); l-(B-hydroxyethyl)-2-methyl-5-aminoindolenine; 2-methyl-5-aminoindolenine; S-aminoindazolone-Ii; 7-amino- 2-oxo-tetrahydroquinoxaline; o-aminotetrahydroquinoxaline. Preparation of the amino compounds used is carried out according to generally known methods, for example, by in- 2 troduction of the amino group-into tlie'corre'sponding'heterocyclic compounds.
Known coupling components on the basis of aromatic compounds containing amino groups or hydroxyl'groups, areQby way of example, diamines, phenols, naphthols, polyphenols and aminophenols. ln-thecase of diamines, aminophenols and phenols,-preferably-the orthoor meta-compounds are used.
As examples of suitable individual compounds, the following are mentioned:
m-phenylenediai'nine pyi'og'allol o-phenyle'nediamine 'resorcinol m-aminophenol pyroca'techol o-anisidine a'minur'eibr'cinol 2,4-diaminoanisole o-toluyle'nediamine m-toluylenediamine 2,4-diaminophenol o-aminophenol l ,5-'dihydi'oxynaphthalene l,S-aminohydroiynaphthnlene l18aminuhydroxynaphihalene 'a-nphthol Furthermore pyrazolones and also aroyl-derivatives or acylacetic acid derivatives come into consideration, for'exarm ple 3-methyIpyrazolone-( 5 l-phenyl-3-methylpyrazolone-(5) l ,3dimethylpyrazolone-(5 3-aminopyrazolone-5 acetoacetic acid anilide benzoylacetanilide benzoylacettoluidide nicotinoylacetanilide.
The coupling components are used "appropriately in about molecularquantities'with relation to'the'heterocyclic aminocompoundsHowever, itis, iii-"general, not detrimental if 'the latter are used in a certainexcessfln some-cases it has been found expedient to apply theheterocyclic amino compou'nds of the above-describedtype in'the form of salts with strong organic or inorganic acids, such *as oxalic acid, maleic' acid, sulfuric acid and hydrochloric acid. The use of the easily accessible hydrochlorides is preferred.
As in'the case of other oxidation dyes, the colorcan be developed by atmospheric'oxygen, aswell as particularly 'by chemical oxidizing agents, e.'g.,preferably hydrogen peroxide and its addition'compounds especially with urea, melamine, and sodium borate. Dyeing of the'hair is carried out in the temperature range of l'5-'40 C., preferably at ordinary room temperature. The hair dyes can be applied in the form of aqueous solutions, particularly however in form of a cream or emulsion. For this purpose the dye components are mixed with any tensides, particularly anionic or nonionog'enic tensides'. Examples of tensides are especially alkylbenzeriesulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamides, additionproducts of'ethyleneoxide to fatty alcohols and alkylphenols.
The absorptive power of the above-named dyes is good, even in mixture with such additions. Therefore,'t he hair dyes can be produced in the form of'shampoo's, particularly creamlike shampoos which are frequently demanded in practice.
Furthermore, to the products according to the invention thickening agents, such'as methylcellulose,starch. higher-fatty alcohols, Vaseline (petrolatum), Paraffin oil, and fatty acids, and also perfume oils or substances 'for the'care of the hair, e.g. pantothenic acid and cholesterol'may be admixed.
Thereby. the admixed material is applied in proportions which are conventional for therespective purpose. Wetting agents can be used especially in proportions of 05-30 percent by weight calculated on the total composition. Thickening agents are added in proportions of 01-25 percent by weight based on the weight of the total composition. Concentration of the dyes amounts-in dependence on the intended useup ing obtained with the hair dyes described herein have good characteristics relative to the effect of light, washing and rubbing andin contrast to conventional products based on oxidation dyes-can be easily removed with reducing agents, such as sodium-hydroxymethanesulfinate.
EXAMPLE 1 Two parts by weight of -aminotetrahydroquinoline hydrochloride, 1 part by weight of a-naphthol and 1 part by weight of hydrogen peroxide are mixed with 96 parts water and adjusted to a pH value of 9.5 with ammonia. Gray human hair is treated with this solution for 20 minutes at 15 C. A deep dark blue coloration is thus obtained.
EXAMPLE 2 A dyeing cream is prepared in the following manner: 1 part by weight of 1-(B-hydroxyethyl)-6-aminotetrahydroquinoline hydrochloride and 1 part by weight of 3-aminopyrazolone-5, are dissolved in an emulsion consisting of 10 parts by weight of fat alcohols having chain lengths of 16-18 carbon atoms, 10 parts by weight of fatty alcohol sulfate based on coconut oil and 70 parts of water and adjusted with ammonia to a pH value of 9. The resulting solution is mixed with 1 part of hydrogen peroxide and filled up with water to 100 parts by weight. If gray hair is treated with this dyeing cream thus prepared at 20 C., for 20 minutes, a red-violet coloration is obtained.
EXAMPLE 3 Dyeing creams, as described in the above example 2, have been prepared, in which, however, as the developer component and the coupling component the compounds stated in the following table were used.
The coloration stated in the right column of said table were obtained by treating gray human hair with the respective creams at 20 C. for 20 minutes.
Equal results are obtained if the heterocyclic amino compounds used and identified in said table as the developer component, are applied in form of the corresponding salts with oxalic acid, maleic acid, sulfuric acid or hydrochloric acid respectively.
TABLE No. Heterocyclic Coupling Coloration amino compound Components 1 l-methyHS-amino- 2,4-diaminogray-green tetrahydroquinoline toluene 2 l-mcthyl-o-aminoresorcinol violet-brown tetrahydroquinoline 3 fi-aminotetra- 2.4-diaminodark-blue hydroquinoline anisole 4 l-ethyl-6-aminoa-naphthol dark-blue tetrahydroquinoline S l-(fl-hydroxycthyK- 2,4-diaminoblue-green o-aminotctrahydrotoluene quinoline 6 4-methyl-7-aminou-naphthol dark-blue dihydrobenzoxazinc- 7 1 -(fl-hydroxyethyl)- a-naphthol dark-blue Z-mcthyl-S-aminoindolenine 8 LmethyLS-aminoa-naphlhol weakly gray indolenine 9 Saminoindazolonea-naphthol weakly gray -3 l 7-amino-2-oxoa-naphthol weakly yellow tetrahydroquinoxaline l l baminotetrahydrm resorcinol yellow quinoxaline l2 l-methyl-6,8-diaminoa-naphthol brown lctrahydroquinolinc l3 l-mcthyl-b-aminoresorcinol dark 8-methoxytelrahydroash-blond quinoline l4 l-ethyl-(a-aminobenloylacclyellow tetrahydroquinoline anilide l l-(lJ-hydroxyethyhl-phenyl-3- purple acetoncctic acidanilide yellowish The term substituents of the first order" is used herein to denote substituents which direct further groups, i.e. nitrogroups, predominately into the oor p-position on an aromatic nucleus.
The generally known methods suggested for the preparation of amino compounds used in carrying out the invention, are described, for example: Weissberger et al., J. Amer. Chem. Soc. 73, 3,100 (1951); Skikoma, J. Chem. Soc. 119, 744; Knuppel, Liebigs Ann. d. Chem. 310, 72 (1899). The excess of the heterocyclic amino compound described above may amount to 3 to 1 mole, based on 1 mol of the coupling compound used.
The term room temperature" is used herein to denote about 18 to 25 C., and the term tensides" is used to denote and include surfactants like alkylbenzenesulfonates (alkyl group C C fatty alcohol sulfates (C -C alkylsulfonates (C -C fatty acid ethanolamides (alkyl group C,,C addition products of ethylene oxide to fatty alcohols (C -C and alkylphenols (alkyl group C -C The weakly acid, neutral and alkaline pH values preferred in carrying out the invention are in the range from 3 to 10.
The hydrogen peroxide used according to the above examples refers to hydrogen peroxide of percent concentration.
The recitation atoms necessary for forming a heterocyclic nonaromatic five-membered (or six-membered) ring means radicals, comprising for example -(CH,),, (CH,) (CH CH(CH --NRCH CH -CH NR CH,,OCH CH (R being H or alkyl group having one-four carbon atoms).
To the dyeing creams used in carrying out the invention conventional amounts of wetting agents and/or washing agents may be added. Suitable examples are 0.5-30 percent by weight of alkylbenzene sulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamides, addition products of ethylene oxide to fatty alcohols and alkylphenols.
The parts and percent mentioned herein are by weight if not otherwise stated.
What is claimed is:
l. A process for the dyeing of human hair which consists essentially of applying to said hair at temperatures ranging substantially from 15 to 40 C. and for a time sufficient to effect dyeing, an effective amount of an aqueous solution containing from 0.1 to 5 percent by weight of a mixture of a coupling component and a developer component in a mole ratio of 1:1 to 1:3 said coupling component being selected from the group consisting of aromatic diamines, phenols, naphthols, aminophenols, 3-methylpyrazoline-( 5 l-phenyl-3-methylpyrazolone-(S 1,3-dimethylpyrazolone-(5 3- aminopyrazolone-( 5 acetoacetic acid anilide, benzoylacetanilide, benzoylacettoluidide and nicotinoylacetanilide and said developer component being selected from the group consisting of l a heterocyclic amino compound of the formula NIIg wherein R, is a member selected from the group consisting of hydrogen, alkyl having one to four carbon atoms and hydroxyalkyl having one to four carbon atoms, R is a member selected from the group consisting of hydrogen, amino, methoxy and ethoxy and X represents a bivalent linkage selected from the group consisting of CH,CH,CH,, CH -CH,-, -CH,CH(CH NR-CH,--CH,-, -O-CH -Cl-1 CONH and NHCOCH where R represents a member selected from the group consisting of hydrogen and alkyl having one to four carbon atoms, and (2) its acid addition salt with a strong acid selected from the group consisting of inorganic and organic acids.
2. The process of claim 1 wherein said heterocyclic amino compound is in the form of an acid addition salt of a strong acid selected from the group consisting of inorganic and organic acids.
3. The process of claim 1 wherein said aqueous solution has a further content of from 0.5 to 30 percent by weight of an agent selected from the group consisting of alkylbenzene sulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamides, ethylene oxide adducts of fatty alcohols and ethylene oxide adducts of alkylphenols.
4. The process of claim 1 wherein said aqueous solution has a further content of a chemical oxidizing agent.
f UNl'lED 's'm'nss PATL'IN'I OFFICE CERTIFICATE OF CO ERECTION 1 -Patcnt: No. 3, 3 55 .'Decerr 1bez 2.8,. 1971 Invencofls) Peter Berth et 8.1
It is eertified that error appears in the above-identified patent and that; sold Letters Patent are hereby corrected as shot-m below:
- rPatent Appln. I I
enga em- .2222 l 25 2 2O In the for-mills "II N" should be H N I. i I I 2 21-23 After the I formula, the following lines were omitted: wherein R stands for a hy- Y drogen atom or for an eliphatic radical having not more than 10 carbon atoms; R
stands for a hydrogen atom or for a substituent of the first order; (Insert meaning, of R and R in. disclosure. This is required for an nnderstanding of the invention) l 59 '4 l" "afminoindolenine (CHphd2) should be.
. 4%)3' b, 61 Claim 1 in Amendment "A' in the formula,
u "NII should be N11 Signed and sealed this-11st day of August,l972.
(SEAL) Attest:
EDWARD M.FLETCHER,JR. ROBERT GQTTSC'HALK Attesting Officer Commissioner of Patents
Claims (4)
- 2. The process of claim 1 wherein said heterocyclic amino compound is in the form of an acid addition salt of a strong acid selected from the group consisting of inorganic and organic acids.
- 3. The process of claim 1 wherein said aqueous solution has a further content of from 0.5 to 30 percent by weight of an agent selected from the group consisting of alkylbenzene sulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamides, ethylene oxide adducts of fatty alcohols and ethylene oxide adducts of alkylphenols.
- 4. The process of claim 1 wherein said aqueous solution has a further content of a chemical oxidizing agent.
- 5. The process of claim 1 wherein said heterocyclic amino compound is selected from the group consisting of 6-amino-tetrahydroquinoline, 1-ethyl-6-aminotetrahydroquinoline, 1-( Beta -hydroxyethyl)-6-aminotetrahydroquinoline, 4-methyl-7-aminodihydrobenzoxaine-(1,4), 1-( Beta -hydroxyethyl)-2-methyl-5-aminoindolenine, 2-methyl-5aminoindolenine, 5-aminoindazolone-3, 7-amino-2-oxo-tetrahydroquinoxaline, 6-aminotetrahydroquinoxaline, 1-methyl-6,8-diaminotetRahydroquinoline diaminotetrahydroquinoline and 1-methyl-6-amino-8-methoxytetrahydroquinoline.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT997767A AT277464B (en) | 1967-11-06 | 1967-11-06 | Hair dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3630655A true US3630655A (en) | 1971-12-28 |
Family
ID=3618898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US769749A Expired - Lifetime US3630655A (en) | 1967-11-06 | 1968-10-22 | Dyeing human hair with oxidation dyes comprising heterocyclic amino compounds |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3630655A (en) |
| AT (1) | AT277464B (en) |
| BE (1) | BE723373A (en) |
| CH (1) | CH537187A (en) |
| DE (1) | DE1804066B2 (en) |
| DK (1) | DK120448B (en) |
| FR (1) | FR1602547A (en) |
| GB (1) | GB1223270A (en) |
| NL (1) | NL159880C (en) |
| SE (1) | SE348368B (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5176377A (en) * | 1974-09-18 | 1976-07-01 | Goodrich Co B F | Jugotaifuchakuno haijohoho |
| US4172703A (en) * | 1978-08-03 | 1979-10-30 | Syntex (Usa) Inc. | Oxidative brown hair dye |
| US4322212A (en) * | 1979-12-13 | 1982-03-30 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation hair dyes comprising substituted benzotriazoles |
| US5190564A (en) * | 1991-02-01 | 1993-03-02 | L'oreal | Process for dyeing keratinous fibres combining isatin or its derivatives with an aminoindole or an aminoindoline, and compositions used |
| US5364414A (en) * | 1989-10-20 | 1994-11-15 | L'oreal | Tinctorial composition for keratinous fibres containing oxidation dye precursors and aminoindole couplers, methods for dyeing using these compositions and new compounds |
| US5474578A (en) * | 1994-10-03 | 1995-12-12 | Clairol, Inc. | Erasable hair dyeing process |
| US5752984A (en) * | 1994-02-12 | 1998-05-19 | Henkel Kommanditgesellschaft Auf Aktien | Use of 1,2,3,4-tetrahydroquinoxalines as oxidation dye precursors in oxidative coloring formulations |
| EP1086685A1 (en) * | 1999-09-24 | 2001-03-28 | GOLDWELL GmbH | Two component kit containing a solution and an emulsion and method for removing hair dye |
| WO2001060327A1 (en) * | 2000-02-16 | 2001-08-23 | Clairol Incorporated | Oxidative hair dyeing system and process for providing more equalized coloration on new and old growth hair |
| US6613313B2 (en) * | 1997-11-28 | 2003-09-02 | Fuji Photo Film Co., Ltd. | Aniline compound-containing hair dye composition and method of dyeing hair |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3825212A1 (en) | 1988-07-25 | 1990-02-01 | Henkel Kgaa | Hair Dye |
| DE4206537A1 (en) * | 1992-03-02 | 1993-09-09 | Henkel Kgaa | NEW FAIRY AGENTS FOR FIBERS OF NATURAL ORIGIN AND SYNTHETIC FIBERS |
| JPH11158047A (en) * | 1997-11-28 | 1999-06-15 | Fuji Photo Film Co Ltd | Hair dye composition compounded with 4-amino-n,n-dialkylaniline compound |
| FR3024728B1 (en) * | 2014-08-08 | 2017-12-01 | Oreal | BENZOXAZINE DERIVATIVES AND USE IN CAPILLARY COLORING. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2196739A (en) * | 1938-09-23 | 1940-04-09 | Eastman Kodak Co | Photographic developer for color photography |
-
1967
- 1967-11-06 AT AT997767A patent/AT277464B/en not_active IP Right Cessation
-
1968
- 1968-07-19 SE SE09944/68A patent/SE348368B/xx unknown
- 1968-07-24 DK DK357768AA patent/DK120448B/en unknown
- 1968-10-09 NL NL6814457.A patent/NL159880C/en not_active IP Right Cessation
- 1968-10-19 DE DE19681804066 patent/DE1804066B2/en active Granted
- 1968-10-22 US US769749A patent/US3630655A/en not_active Expired - Lifetime
- 1968-11-05 GB GB52357/68A patent/GB1223270A/en not_active Expired
- 1968-11-05 BE BE723373D patent/BE723373A/xx unknown
- 1968-11-05 FR FR1602547D patent/FR1602547A/fr not_active Expired
- 1968-11-05 CH CH1646568A patent/CH537187A/en not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2196739A (en) * | 1938-09-23 | 1940-04-09 | Eastman Kodak Co | Photographic developer for color photography |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5916561B2 (en) * | 1974-09-18 | 1984-04-16 | ザ ビ− エフ グツドリツチ カムパニ− | How to eliminate polymer adhesion |
| JPS5176377A (en) * | 1974-09-18 | 1976-07-01 | Goodrich Co B F | Jugotaifuchakuno haijohoho |
| US4172703A (en) * | 1978-08-03 | 1979-10-30 | Syntex (Usa) Inc. | Oxidative brown hair dye |
| US4322212A (en) * | 1979-12-13 | 1982-03-30 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation hair dyes comprising substituted benzotriazoles |
| US5364414A (en) * | 1989-10-20 | 1994-11-15 | L'oreal | Tinctorial composition for keratinous fibres containing oxidation dye precursors and aminoindole couplers, methods for dyeing using these compositions and new compounds |
| US5190564A (en) * | 1991-02-01 | 1993-03-02 | L'oreal | Process for dyeing keratinous fibres combining isatin or its derivatives with an aminoindole or an aminoindoline, and compositions used |
| US5752984A (en) * | 1994-02-12 | 1998-05-19 | Henkel Kommanditgesellschaft Auf Aktien | Use of 1,2,3,4-tetrahydroquinoxalines as oxidation dye precursors in oxidative coloring formulations |
| US5474578A (en) * | 1994-10-03 | 1995-12-12 | Clairol, Inc. | Erasable hair dyeing process |
| US6613313B2 (en) * | 1997-11-28 | 2003-09-02 | Fuji Photo Film Co., Ltd. | Aniline compound-containing hair dye composition and method of dyeing hair |
| EP1086685A1 (en) * | 1999-09-24 | 2001-03-28 | GOLDWELL GmbH | Two component kit containing a solution and an emulsion and method for removing hair dye |
| US6379657B1 (en) | 1999-09-24 | 2002-04-30 | Goldwell Gmbh | Composition and process for de-coloring dyed hair |
| WO2001060327A1 (en) * | 2000-02-16 | 2001-08-23 | Clairol Incorporated | Oxidative hair dyeing system and process for providing more equalized coloration on new and old growth hair |
| US6379399B1 (en) | 2000-02-16 | 2002-04-30 | Bristol-Myers Squibb Company | Oxidation hair dyeing systems and process for providing more equalized coloration on new and old growth hair |
Also Published As
| Publication number | Publication date |
|---|---|
| CH537187A (en) | 1973-05-31 |
| BE723373A (en) | 1969-05-05 |
| NL159880C (en) | 1979-09-17 |
| GB1223270A (en) | 1971-02-24 |
| NL6814457A (en) | 1969-05-08 |
| SE348368B (en) | 1972-09-04 |
| AT277464B (en) | 1969-12-29 |
| FR1602547A (en) | 1970-12-21 |
| DE1804066B2 (en) | 1976-11-18 |
| DE1804066A1 (en) | 1969-09-04 |
| NL159880B (en) | 1979-04-17 |
| DK120448B (en) | 1971-06-01 |
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