US3690810A - Benzomorpholine couplers and oxidation bases for dyeing live human hair - Google Patents

Benzomorpholine couplers and oxidation bases for dyeing live human hair Download PDF

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US3690810A
US3690810A US847413A US3690810DA US3690810A US 3690810 A US3690810 A US 3690810A US 847413 A US847413 A US 847413A US 3690810D A US3690810D A US 3690810DA US 3690810 A US3690810 A US 3690810A
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benzomorpholine
dyeing
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human hair
hair
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Andree Bugaut
Francoise Estradier
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LOreal SA
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LOreal SA
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring

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  • the present invention relates to a new class of couplers which may be used with known oxidation dyes. It is the object of the invention to provide as a new article of manufacture a dye for keratinic fibers, and particularly for human hair, which is essentially characterized by the fact that it contains, in association with at least one conventional oxidation base, at least one benzomorpholine compound having the general formula:
  • R represents hydroxyl or amino in position or 7
  • R and R represent hydrogen, lower alkyl having 1-4 carbon atoms or lower hydroxyl alkyl having 14 carbon atoms
  • R is H or lower alkyl having 1 to 4 carbon atoms.
  • bases which may be advantageously used in association with the couplers of Formula I are: para-phenylene diamine, para-tolylene diamine, para-aminophenol, N-methyl-para-aminophenol, chloroparaphenylene diamine, methoxy-para-phenylene diamine, 6-methoxy-3-methyl-para-phenylene diamine, (N-ethyl, N- carbamylethyl)para-phenylene-diamine, 2,5-diamino-pyridine.
  • couplers having Formula I are: 7-hydroxybenzomorpholine, 7-amino-benzomorpholine, S-hydroxybenzomorpholine, S-amino-benzomorpholine, 1-methyl-7- hydroxy-benzomorpholine, 2-methy1-7-hydroxy-benzomorpholine and 5-hydroxy-7methyl-benzomorpholine.
  • the ratio of base to coupler in the dyeing compositions according to the invention may vary within broad limits, but an excess of coupler is preferably used.
  • the dyeing compositions of this invention may contain other dyes suitable for use under the same conditions, including direct dyes (such as azo or anthraquinone dyes), or dyes obtained by the association of bases and couplers other than those constituting the subject matter of the present invention.
  • direct dyes such as azo or anthraquinone dyes
  • dyes obtained by the association of bases and couplers other than those constituting the subject matter of the present invention include direct dyes (such as azo or anthraquinone dyes), or dyes obtained by the association of bases and couplers other than those constituting the subject matter of the present invention.
  • compositions of this invention may also contain wetting agents, dispersing agents, penetrating agents, or any other ingredients conventionally used in dyeing hair. They may take the form of an aqueous solution, a cream, a gel or an aerosol.
  • compositions according to the invention are used in a conventional manner at an alkaline pH, preferably between 8 and 10. This pH may be obtained, for example, by adding ammonia or some other base.
  • the composition is applied to the hair in the presence of an oxidizing solution, which is preferably a solution of hydrogen peroxide.
  • -It is a further object of the present invention to provide a method of dyeing hair which is characterized by making the dye composition defined above alkaline, adding hydrogen peroxide thereto and applying the mixture to the hair. The hair is then rinsed, shampooed and dried.
  • a further object of the invention is to provide new compounds having the Formula I in which R represents hydroxyl, that is to say those compounds having the formula:
  • CH3 I 11 NH Ca 7 and the organic and mineral acid salts of the above compounds.
  • the preferred organic acid salts are the salts of acetic acid, formic acid, propionic acid, etc.
  • the preferred mineral acid salts are salts of the halogen acids, such as hydrochloric acid, hydrobromic acid, or of sulfuric acid, phosphoric acid, etc.
  • the preferred hair dye compositions may contain 0.1 to 10% of the coupler compound and 0.1 to 10% of the oxidation base dye.
  • oxidation dye-coupler compositions of this invention may be placed in any suitable carrier such as water, alcohol, etc. and they may be in any suitable form such as solution, gel, cream, aerosol, etc.
  • suitable carriers, gelling agnts, aerosol compositions, etc. are set forth in many text books, such as Cosmetic Compositions, volumes I and II, by Harry.
  • a hair dye composition for dyeing live human hair comprising an aqueous alkaline solution having a pH of 8-10 of an oxidation base consisting of a compound in which the molecule comprises an aromatic nucleus having either two amino groups or an amino group and a hydroxyl group in ortho or para position with respect to each other;
  • a coupler selected from the group consisting of a compound having the formula wherein X is selected from the group consisting of sulfur and oxygen, R is selected from the group consisting of hydroxyl and NH in position 5 or 7, R and R are selected from the group consisting of hydrogen, lower alkyl and lower hydroxyl alkyl, R is selected from the group consisting of hydrogen and lower alkyl, and the acid addition salts of said compound, and an effective amount of an oxidizing agent, said oxidation base being present in amounts of 0.1-10% by weight of said composition and said coupler being present in amounts of 0.1-10 percent by weight of said composition.
  • composition of claim 1 in which the base is selected from the group consisting of para-phenylene diamine, para toluylene diamine, para aminophenol, N-methyl-para-aminophenol, 6 methoxy-3-methyl-paraphenylene diamine, (N-ethyl, N-carbamyl-ethyl)-paraphenylene diamine and 2,5-diaminopyridine.
  • composition of claim 1 in which the coupler is selected from the group consisting of 7-hydroXy-benzomorpholine, 5-hydroxy-benzomorpholine, 7-amino-benzomorpholine, S-amino-benzomorpholine, 1 methyl-7-hydroxy-benzomorpholiue, 2-methyl 7 hydroxy-benzomorpholine and S-hydroxy 7-methyl-benzornorpholine.
  • a process for dyeing live human hair comprising applying in amounts effective to dye said hair, the composition of claim 1.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

OXIDATION DYE COUPLING COMPOUNDS FOR USE IN DYEING LIVE HUMAN HAIR HAVING THE FORMULA:

X<(-(R,R3-1,2-PHENYLENE)-N(-R1)-CH(-R2)-CH2-)

Description

United States Patent Qfice Patented Sept. 12, 1972 Int. Cl. A01k 7/12 Us. or. s-10.z 4 Claims ABSTRACT OF THE DISCLOSURE Oxidation dye coupling compounds for use in dyeing live human hair having the formula:
SUMMARY OF THE INVENTION There are methods of dyeing keratinic fibers, and particularly human hair, in which the hair is dyed by means of compositions containing oxidation dyes, and in particular by means of aromatic ortho or para-diamines and orthoor para-aminophenols, which are generally referred to as oxidation bases. It is also conventional to vary the shades obtained with these bases by utilizing color modifiers or couplers and, in particular, aromatic meta diamines and meta aminophenols.
The present invention relates to a new class of couplers which may be used with known oxidation dyes. It is the object of the invention to provide as a new article of manufacture a dye for keratinic fibers, and particularly for human hair, which is essentially characterized by the fact that it contains, in association with at least one conventional oxidation base, at least one benzomorpholine compound having the general formula:
in which X represents sulfur or oxygen, R represents hydroxyl or amino in position or 7, R and R represent hydrogen, lower alkyl having 1-4 carbon atoms or lower hydroxyl alkyl having 14 carbon atoms, and R is H or lower alkyl having 1 to 4 carbon atoms. These compounds may be used in the form of their mineral or organic acid addition salts. Among the bases which may be advantageously used in association with the couplers of Formula I are: para-phenylene diamine, para-tolylene diamine, para-aminophenol, N-methyl-para-aminophenol, chloroparaphenylene diamine, methoxy-para-phenylene diamine, 6-methoxy-3-methyl-para-phenylene diamine, (N-ethyl, N- carbamylethyl)para-phenylene-diamine, 2,5-diamino-pyridine.
Among the couplers having Formula I .are: 7-hydroxybenzomorpholine, 7-amino-benzomorpholine, S-hydroxybenzomorpholine, S-amino-benzomorpholine, 1-methyl-7- hydroxy-benzomorpholine, 2-methy1-7-hydroxy-benzomorpholine and 5-hydroxy-7methyl-benzomorpholine.
The ratio of base to coupler in the dyeing compositions according to the invention may vary Within broad limits, but an excess of coupler is preferably used.
The dyeing compositions of this invention may contain other dyes suitable for use under the same conditions, including direct dyes (such as azo or anthraquinone dyes), or dyes obtained by the association of bases and couplers other than those constituting the subject matter of the present invention.
The compositions of this invention may also contain wetting agents, dispersing agents, penetrating agents, or any other ingredients conventionally used in dyeing hair. They may take the form of an aqueous solution, a cream, a gel or an aerosol.
The compositions according to the invention are used in a conventional manner at an alkaline pH, preferably between 8 and 10. This pH may be obtained, for example, by adding ammonia or some other base. The composition is applied to the hair in the presence of an oxidizing solution, which is preferably a solution of hydrogen peroxide.
-It is a further object of the present invention to provide a method of dyeing hair which is characterized by making the dye composition defined above alkaline, adding hydrogen peroxide thereto and applying the mixture to the hair. The hair is then rinsed, shampooed and dried.
A further object of the invention is to provide new compounds having the Formula I in which R represents hydroxyl, that is to say those compounds having the formula:
I N HO will \ AX n N R3 R2 NHz in which the amino group is in position 5 or 7. In this process chloroethyl chloroformiate is condensed in a first step with a 2-methoxy-5-nitro aniline or with a Z-methoxy- 3-nitro aniline in order to obtain the corresponding chloroethyl carbamate. This is cyclized with a strong mineral base such as sodium hydroxide or potassium hydroxide. Then the nitro group of the resulting compound is reduced with a reducing agent, such as iron in an aqueous acetic acid medium.
The following examples illustrate the ditferent forms of the invention. In these examples, which are purely illustrative, the percentages are given by weight and the temperatures are indicated in degrees Celsius, that is to say degrees centigrade.
EXAMPLES OF PREPARATION Example 1.Preparation of 7-hydroxy benzomorpholine This process may be schematically described as follows:
(1) Preparation of 2,5-dimethoxy-N-(B-hydroxyethyl) aniline.A mixture containing 100 g. (0.654 mole) of 2,5-dimethoxy aniline, 147.5 g. (0.825 mole) of 70% glycol bromohydrin, 45 g. (0.45 mole) of calcium carbonate and 500 cm. of water is heated at reflux for 4 hours. After cooling and filtering the reaction mixture, it is extracted using ethyl acetate. The solvent is eliminated under vacuum and the oily residue is fractionally distilled. The yield is 62 g. of 2,5-dimethoxy-N-(fi-hydroxyethyl) aniline, boiling point at 0.05 m.=137142, melting point=48.5, which analyzes as follows:
Analysis.Calculated for C H NO (percent): C, 60.91; H, 7.61; N, 7.10. Found (percent): C, 60.81; H, 7.63; N, 7.01.
(2) Preparation of 7 hydroxy-benzomorpholine.8 g. (0.04 mole) of 2,5 dimethoxy-N-(fi-hydroxyethyl) aniline are heated at reflux for 2 hours in cm. of hydrobromic acid having a density of 1.78. After cooling the reaction mixture, 6 g. of 7-hydroxy-benzomorpholine hydrobromide are separated out by drying. This hydrobromide is dissolved in water and the aqueous solution is neutralized with ammonia. Drying then yields 3.5 g. of 7-hydroxy-benzomorpholine which, after recrystallization in toluene, melts at 115.
Analysis.--Calculated for C H NO (percent): C, 63.57; H, 5.96; N, 9.27. Found (percent): C, 63.51; H, 6.02; N, 9.44.
Eample 2.Preparation of 7-amino-benzomorpholine ll OzN NH-G-O-CHrOHz-Cl OCH lKOH
l Fe, orncoirr H COCHs /N N Hm HCl HzC-COHN zrroi \o (1) Preparation of ,6-chloroethyl-N-[(2 methoxy-S- nitro) phenyl] carbamate-63 g. (0.37 mole) of Z-amino- 4-nitro anisole are dissolved in 190 cm. of dioxane. 26 g. (0.26 mole) of calcium carbonate are then added. The mixture is brought to reflux and 63 g. (0.44 mole) of B-chloroethyl chloroformiate are added little by little. After heating for an hour the boiling liquid is filtered. The filtrate is cooled, and drying yields g. of fl-chloroethyl N [(2 methoxy 5 nitro) phenyl] carbamate which, after recrystallization in dioxane, melts at 130.
(2) Preparation of 7-nitro-benzomorpholine.-68.6 g. (0.25 mole) 9 chloroethyl N [(2 methoxy-S-nitro) phenyl] carbamate are added to 600 cm. of ethyl alcohol at containing 66 g. of 85% potassium hydroxide. This is heated at reflux for 2 hours under a nitrogen atmosphere. After cooling, the reaction mixture is diluted with 2 liters of ice water and drying yields 43 g. of 7-nitro-benzomorpholine which, after recrystallization in benzene, melts at 120.
Analysis.Calculated for C H O N (percent): C, 53.30; H, 4.44; N, 15.55. Found (percent): C, 53.51, 53.40; H, 4.48, 4.60; N, 15.49, 15.54.
(3) Preparation of 1 acetyl 7 acetylamino-benzomorpholine.--7 g. (0.039 mole) of 7 nitro-benzomorpholine are introduced into 40 cm. of Water containing 1.5 cm. of acetic acid and 8.8 g. of iron powder. The reaction mixture is brought to 80 for 20 minutes and neutralized with sodium carbonate. It is boiled dry and the filtrate introduced directly into 15 cm. of acetic anhydride. After cooling, drying yields 6.5 g. of l-acetyl- 7 acetylamino-benzomorpholine which, after recrystallization in alcohol, melts at 198.
Analysis-Calculated for C H N O (percent): C, 61.53; H, 5.98; N, 11.96. Found (percent): C, 61.93, 61.91; H, 6.22, 6.22; N, 11.91, 11.92.
(4) Preparation of 7 amino benzomorpholine dihydrochloride.3 g. (0.0138 mole) of 1-acetyl-7-acetylamino-benzomorpholine are introduced into 9 cm. of concentrated hydrochloric acid, and the reaction mixture is brought to reflux for 2 hours. After cooling to -10, drying yields 2.3 g. of 7 amino benzomorpholine didydrochloride which melts and decompose at 235-240". Calculated molecular weight for C H N OCl :223. Molecular weight found by potentiometric measurementz233.
EXAMPLES OF APPLICATION Ethylene diamino tetra acetic acid 3 20% ammonia 40% sodium bisulfite 10 Water q.s.p. 1000 g.
This solution, when mixed with an equal weight of 6% hydrogen perioxide and applied for 30 minutes to 100% white hair, produces a purplish-blue.
Example 4 The following dyeing solution is prepared:
1 G. Para-toluylene diamine 3 6-methyl 3 methoxy para-phenylene diamine dihydrochloride 5 7-hydroxy-benzomorpholine 5 Meta-diamino anisole sulfate 4 4-(7-an1inopr0py1) -amino 1 methylamino-anthraquinone 0.5 20% ammonium lauryl sulfate 200 Ethylene diamino tetra-acetic acid 3 20% ammonia 100 40% sodium bisulfite Water q.s.p. 1000 g.
This solution, when mixed with an equal weight of 6% hydrogen peroxide and applied for 30 minutes to 100% white hair, produces a deep green.
Example 5 The following dyeing solution is prepared:
G. 2,5-diamino-4-methyl anisole dihydrochloride 1 7-hydroxy benzomorpholine 0.7 20% ammonium lauryl sulfate 20 Ethylene diamino tetra-acetic acid 0.3 20% ammonia 10 40% sodium bisulfite 1 Water q.s.p. 100 g.
This solution, when mixed with an equal weight of 6% hydrogen peroxide and applied for 30 minutes to 100% white hair, produces a greenish brown.
'Example 6 The following dyeing solution is prepared:
G. 2,5-diamino-4,6-dimethyl anisole dihydrochloride 1 7-hydroxy-benzomorpholine 1.1 20% ammonium lauryl sulfate 20 Ethylene diamino tetra-acetic acid 0.3 20% ammonia 10 40% sodium bisulfite 1 Water q.s.p. 100 g.
This solution, when mixed with an equal weight of 6% hydrogen peroxide and applied for 30 minutes to 100% white hair, produces a bright gray with green glints.
Example 7 The following dyeing solution is prepared:
G. Para-toluylene diamine 1 Resorcinol 0.1 2,5-diarnino4-methyl anisole dihydrochloride n 0.2 7-hydroxy-benzomorpholine 1.3 20% ammonium lauryl sulfate 20 Ethylene diamino tetra-acetic acid 0.3 20% ammonia 10 40% sodium bisulfite 1 Water q.s.p. 100 g.
This solution, when mixed with an equal Weight of 6% hydrogen peroxide and applied for 30 minutes to 100% white hair, produces a greenish brown which is very stable under exposure to light.
Other illustrative coupling compounds of this invention are:
CH3 I 11: NH Ca 7 and the organic and mineral acid salts of the above compounds.
The preferred organic acid salts are the salts of acetic acid, formic acid, propionic acid, etc.
The preferred mineral acid salts are salts of the halogen acids, such as hydrochloric acid, hydrobromic acid, or of sulfuric acid, phosphoric acid, etc.
The preferred hair dye compositions may contain 0.1 to 10% of the coupler compound and 0.1 to 10% of the oxidation base dye.
The oxidation dye-coupler compositions of this invention may be placed in any suitable carrier such as water, alcohol, etc. and they may be in any suitable form such as solution, gel, cream, aerosol, etc. Suitable carriers, gelling agnts, aerosol compositions, etc. are set forth in many text books, such as Cosmetic Compositions, volumes I and II, by Harry.
What is claimed is:
1. A hair dye composition for dyeing live human hair comprising an aqueous alkaline solution having a pH of 8-10 of an oxidation base consisting of a compound in which the molecule comprises an aromatic nucleus having either two amino groups or an amino group and a hydroxyl group in ortho or para position with respect to each other;
a coupler selected from the group consisting of a compound having the formula wherein X is selected from the group consisting of sulfur and oxygen, R is selected from the group consisting of hydroxyl and NH in position 5 or 7, R and R are selected from the group consisting of hydrogen, lower alkyl and lower hydroxyl alkyl, R is selected from the group consisting of hydrogen and lower alkyl, and the acid addition salts of said compound, and an effective amount of an oxidizing agent, said oxidation base being present in amounts of 0.1-10% by weight of said composition and said coupler being present in amounts of 0.1-10 percent by weight of said composition.
2. The composition of claim 1 in which the base is selected from the group consisting of para-phenylene diamine, para toluylene diamine, para aminophenol, N-methyl-para-aminophenol, 6 methoxy-3-methyl-paraphenylene diamine, (N-ethyl, N-carbamyl-ethyl)-paraphenylene diamine and 2,5-diaminopyridine.
3. The composition of claim 1 in which the coupler is selected from the group consisting of 7-hydroXy-benzomorpholine, 5-hydroxy-benzomorpholine, 7-amino-benzomorpholine, S-amino-benzomorpholine, 1 methyl-7-hydroxy-benzomorpholiue, 2-methyl 7 hydroxy-benzomorpholine and S-hydroxy 7-methyl-benzornorpholine.
4. A process for dyeing live human hair comprising applying in amounts effective to dye said hair, the composition of claim 1.
References Cited UNITED STATES PATENTS Fischer 96100 X Peterson 96100 X McNally et a]. 260247.5 R Dickey et al. 260-247 Strain et al. 260247 X Towne et a1. 260158 X Towne et al. 260158 X Towne et al. 260158 ALBERT T. MEYERS, Primary Examiner V. C. CLARKE, Assistant Examiner US. Cl. X.R.
8-11; 260247.1, 217.5 B, 247.7 R, 247.7 A
US847413A 1968-08-13 1969-08-04 Benzomorpholine couplers and oxidation bases for dyeing live human hair Expired - Lifetime US3690810A (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5055110A (en) * 1989-11-22 1991-10-08 Clairol Incorporated Benzoxazine dyes
US5374288A (en) * 1993-12-27 1994-12-20 Clairol Incorporated Oxidative hair dyeing method, composition, and kit utilizing hydroxyl substituted benzothiazines
US5690695A (en) * 1994-05-26 1997-11-25 L'oreal Composition for the oxidation dyeing of keratinous fibres, comprising a para-phenylenediamine derivative and a 6-hydroxy-1, 4-benzomorpholine and dyeing process using such a composition
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
US5785717A (en) * 1995-02-27 1998-07-28 L'oreal Composition for the oxidation dyeing of keratin fibers, comprising a diaminopyrazole derivative and a heterocyclic coupler, and dyeing process
US6395042B1 (en) * 1998-11-20 2002-05-28 L'oréal Composition for the oxidation dyeing of keratin fibers and dyeing process using this composition
CN111170958A (en) * 2019-12-25 2020-05-19 浙江鼎龙科技有限公司 Preparation method of hydroxybenzomorph

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2813076C2 (en) * 1978-03-25 1986-10-16 Henkel Kgaa, 4000 Duesseldorf Hair dye
FR2704149B1 (en) * 1993-04-23 1995-06-09 Oreal USE OF DERIVATIVES OF BENZOMORPHOLINE OR 3,4-DIHYDRO-2H-1,4 BENZOXAZINE IN COSMETIC OR DERMOPHARMACEUTICAL COMPOSITIONS WITH DEPIGMENTING ACTION.
DE19646609A1 (en) * 1996-11-12 1998-05-14 Wella Ag Colorants for producing metamerism effects on keratin fibers

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL69995C (en) 1946-12-14
NL98806C (en) 1955-11-18
GB805746A (en) 1955-11-18 1958-12-10 Oreal Improvements in or relating to the dyeing of animal fibres
DE1103934B (en) 1959-08-08 1961-04-06 Henkel & Cie Gmbh Process for the preparation of new organic perhydrate compounds
GB896197A (en) 1959-08-08 1962-05-09 Therachemie Chem Therapeut Compositions for the oxidative treatment of hair

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5055110A (en) * 1989-11-22 1991-10-08 Clairol Incorporated Benzoxazine dyes
EP0592396A4 (en) * 1989-11-22 1992-09-28 Bristol Myers Squibb Co Benzoxazine dyes.
EP0592396A1 (en) * 1989-11-22 1994-04-20 Bristol Myers Squibb Co Benzoxazine dyes.
US5374288A (en) * 1993-12-27 1994-12-20 Clairol Incorporated Oxidative hair dyeing method, composition, and kit utilizing hydroxyl substituted benzothiazines
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
US5690695A (en) * 1994-05-26 1997-11-25 L'oreal Composition for the oxidation dyeing of keratinous fibres, comprising a para-phenylenediamine derivative and a 6-hydroxy-1, 4-benzomorpholine and dyeing process using such a composition
US5868800A (en) * 1994-05-26 1999-02-09 L'oreal Composition for the oxidation dyeing of keratinous fibres, comprising a para-phenylenediamine derivative and a 6-hydroxy-1, 4-benzomorpholine and dyeing process using such a composition
US5785717A (en) * 1995-02-27 1998-07-28 L'oreal Composition for the oxidation dyeing of keratin fibers, comprising a diaminopyrazole derivative and a heterocyclic coupler, and dyeing process
US6395042B1 (en) * 1998-11-20 2002-05-28 L'oréal Composition for the oxidation dyeing of keratin fibers and dyeing process using this composition
CN111170958A (en) * 2019-12-25 2020-05-19 浙江鼎龙科技有限公司 Preparation method of hydroxybenzomorph

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BE737265A (en) 1970-02-09
FR2015589A1 (en) 1970-04-30
GB1245524A (en) 1971-09-08
LU56703A1 (en) 1970-02-13
NL6912084A (en) 1970-02-17
DE1940085A1 (en) 1970-02-19
CH511605A (en) 1971-08-31
DE1940085C3 (en) 1979-06-28
CA974993A (en) 1975-09-23

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