US3210252A - 1-methyl-2-hydroxy-4-aminobenzene as a modifier for oxidation dyes - Google Patents
1-methyl-2-hydroxy-4-aminobenzene as a modifier for oxidation dyes Download PDFInfo
- Publication number
- US3210252A US3210252A US240471A US24047162A US3210252A US 3210252 A US3210252 A US 3210252A US 240471 A US240471 A US 240471A US 24047162 A US24047162 A US 24047162A US 3210252 A US3210252 A US 3210252A
- Authority
- US
- United States
- Prior art keywords
- methyl
- hair
- hydroxy
- diaminobenzene
- benzene
- 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.)
- Expired - Lifetime
Links
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 title claims description 19
- 230000003647 oxidation Effects 0.000 title description 5
- 238000007254 oxidation reaction Methods 0.000 title description 5
- 239000000975 dye Substances 0.000 title description 4
- 239000003607 modifier Substances 0.000 title 1
- 238000004043 dyeing Methods 0.000 claims description 37
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 23
- JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical compound NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 claims description 14
- 239000007800 oxidant agent Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 7
- KNRVAYVZVIKHHL-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine Chemical compound COC1=CC(N)=C(C)C=C1N KNRVAYVZVIKHHL-UHFFFAOYSA-N 0.000 claims description 7
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 claims description 7
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 claims description 7
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 claims description 5
- LQRIGLBCGDDYDR-UHFFFAOYSA-N 2-chloro-5-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=C(Cl)C=C1N LQRIGLBCGDDYDR-UHFFFAOYSA-N 0.000 claims description 5
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 32
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000012153 distilled water Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 description 9
- 230000037308 hair color Effects 0.000 description 9
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000000118 hair dye Substances 0.000 description 5
- -1 1,4-diaminobenzene 1,2,4-triaminobenzene 1-methyl-2,5-diaminobenzene Chemical compound 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 229960003742 phenol Drugs 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- 241000158728 Meliaceae Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- YGOFNNAZFZYNIX-UHFFFAOYSA-N 3-N-phenylbenzene-1,2,3-triamine Chemical compound NC=1C(=C(C=CC1)NC1=CC=CC=C1)N YGOFNNAZFZYNIX-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- YBZUKWAMZWDJTR-UHFFFAOYSA-N benzene-1,2,4-triamine;hydrochloride Chemical compound Cl.NC1=CC=C(N)C(N)=C1 YBZUKWAMZWDJTR-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- A61Q5/10—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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22D—CASTING OF METALS; CASTING OF OTHER SUBSTANCES BY THE SAME PROCESSES OR DEVICES
- B22D19/00—Casting in, on, or around objects which form part of the product
- B22D19/0009—Cylinders, pistons
Definitions
- the present invention relates to a method and composition for the dyeing of hair and the like, particularly human hair.
- oxidative dyeing of keratin-containing material can be carried out so as to obtain brilliant colors of high stability, by applying to the material which is to be dyed, such as living hair, a mixture of one or more aromatic p-diamines and/or one or more p-aminophenols, together with 1-methy1-2-hydroxy-4-aminobenzene.
- Very clear and pure color shades are obtained by applying equimolar amounts of a .p-aminophenol or aromatic p-diamine and of 1-methyl-2-hydroxy-4-aminobenzene.
- the above described mixture may be applied as an aqueous or alcoholic solution, or dispersed in other suittempted to dye living human hair in this manner, serious 1 ditficulties were encountered due to the fact that the requirements in connection with dyeing living human hair are, of course, much more strict than those pertaining to the dyeing of furs or cut, dead hair.
- the compositions used for dyeing living hair should be non-toxic and should not cause allergies.
- the dyed living hair should maintain its color even when subjected to sunlight, moisture, acidic sweat, hair washing compositions and other chemicals used in the care of living hair, for instance hair waving and fixing preparations. It is desired that the developed hair dye on the living hair should be resistant against the above mentioned and other influences so that the desired and initially obtained color will be maintained.
- the color obtained by dyeing hair with a given composition should be the same regardless of the color of the undyed hair.
- the dyeing of hair according to the present invention may serve the purpose of giving to the hair the thus obtained color, or to shade thereby the hair color obtained by means of other hair dyeing compositions.
- the dyeing composition may be applied in any desired consistency, preferably in liquid or cream-like consistency.
- the dyeing composition may be adjusted so as to react slightly alkaline, neutral or slightly acidic, broadly within a pH range from 2 to 11. In many cases it is particularly advantageous and will result in colors of greater lumi-.
- the dyeing composition contains 1-methyl-2-hydroxy-4-aminobenzene.
- any aromatic pdiamine or p-aminophenol may be used.
- 1,4-diaminobenzene 1,2,4-triaminobenzene 1-methyl-2,5-diaminobenzene l,4-dimethyl-2,5 diaminobenzene l-methoxy-4-chloro-2,S-diaminobenzene 1-methoxy-4-methyl-2,S-diaminobenzene 1-amino-4-hydroxy-benzene 1-amino-2-methyl-4-hydroxy-benzene 1-amino-3 -m ethyl-4-hydroxy-benzene l,3-diamino-4-hydroxy-benzene 4,4-diaminodiphenylamine
- detergents such as Other objects and advantages of the present invention fatty alcohol sulfonates, alkyl-aryl sulfonates, condensates of fatty alcohol-polyethylene oxide or fatty acid-methyltaurine condensation products; or thickening agents such as
- Suitable alcohols for forming an alcoholic or aqueous alcoholic solution of the essential components of the dyeing composition include ethanol, isopropanol and polyglycols.
- additives which may be included in the dyeing composition of the present invention comprise perfume oils, certain essential oils and the like.
- Example I A solution is formed of:
- the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide and applied to the hair for between 20 and 30 minutes at body temperature- Thereafter, the hair is rinsed to remove the excess of the dyeing solution. In this manner a deep violet hair. color is obtained.
- the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. A deep blue-violet hair color is obtained.
- Example 111 A solution is formed of:
- the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated With the thus formed mixture as described in Example I. A deep, full orange hair color is obtained.
- Example IV A solution is formed of:
- the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. A deep red-violet hair color is obtained.
- Example V A solution is formed of:
- the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. In this manner, beautiful ruby-colored hair is obtained.
- Example VI A solution is formed of:
- the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. A bluish-black hair color is obtained.
- Acetic acid is added so as to adjust the pH of the solution to 5.
- the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. A dark chestnut brown hair color is obtained.
- Example VIII A solution is formed of:
- the solution is adjusted to pH 7 (for adjusting the pH of the dyeing solutions, preferably either acetic acid or ammonia solution is used).
- the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated With the thus formed mixture as described in Example I. A dark mahogany hair color is obtained.
- Example IX 20 grams 12% potassium oleate solution in 30 grams distilled water, are stirred into 15 grams molten fatty alcohol.
- a smooth cream is obtained.
- a solution of the composition described below is stirred into the thus obtained cream:
- Example X A solution is formed of:
- a method of dyeing hair comprising the step of applying to hair which is to be dyed 1-methyl-2-hydroxy- 4-aminobenzene, at least one substance selected from the group consisting of 1-methyl-2,S-diaminobenzene, 1,4-diaminobenzene, 1,2,4-triaminobenzene, 1-methyl-2,5-diaminobenzene, 1,4-dimethyl-2,S-diaminobenzene, l-methoxy-4-chloro-2,5-diaminobenzene, 1-methoxy-4-methyl- 2,5-diaminobenzene, l-amino 4 hydroxy benzene, 1 amino-2-methyl-4-hydroxy-benzene, 1-amino-3-methyl-4- hydroxy-benzene, 1,3-diamino-4-hydroxy-benzene and 4,4-diaminodiphenylamine, and an effective amount of an oxidizing agent therefor.
- a method of dying hair comprising the step of applying to hair which is to be dyed substantially equimolar quantities of 1-methy1-2-hydroxy-4-aminobenzene, and of at least one substance selected from the group consisting of 1-methyl-2,5-diaminobenzene, 1,4-diaminobenzene, 1,2,4-triaminobenzene, 1-methyl-2,5-diamino benzene, 1,4-dimethyl-2,S-diaminobenzene, 1-methoxy-4- chlor0-2,5-diaminobenzene, 1-methoxy-4-methyl-2,5-di aminobenzene, 1-amino-4-hydroxy-benzene, 1-amino-2- methyl-4-hydroxy-benzene, 1-amino-3-methyl-4-hydroxybenzene, 1,3-diamino-4-hydroxy-benzene, and 4,4-diaminodiphenylamine, and an effective amount of hydrogen peroxide as an oxid
- a method of dyeing hair comprising the step of applying to hair which is to be dyed 1-methyl-2-hydroxy- 4-aminobenzene, at least one aromatic p-diamine adapted to form a hair dye upon oxidation, and an effective amount of oxidizing agent therefor.
- a method of dyeing hair comprising the step of applying to hair which is to be dyed I-methyl-Z-hydroxy- 44aminobenzene, :at least one p-aminop'henol adapted to form a hair dye upon oxidation, and an effective amount of oxidizing agent therefor.
- a method of dyeing hair comprising the step of applying to hair which is to be dyed a carrier substance compatible With hair and having distributed therethrough substantially equimolar quantities of 1 methyl 2 hydroxy- 4 aminobenzene, and of at least one substance selected from the group consisting of 1 methyl 2,5 diaminobenzene, 1,4 diaminobenzene, 1,2,4 triaminobenzene, 1 methyl 2,5 diaminobenzene, 1,4 dimethyl 2,5- diaminobenzene, 1 methoxy 4 chloro 2,5 diaminobenzene, 1 methoxy 4 methyl 2,5 diaminobenzene, 1 amino 4 hydroxy benzene, 1 amino 2 methyl- 4 hydroxy benzene, 1 amino 3 methyl 4 hydroxy benzene, 1,3 diamino 4 hydroxy benzene and 4,4-diaminodiphenylamine, and an effective amount of hydrogen peroxide as an oxidizing agent therefor.
- a composition of matter for dyeing of hair which comprises 1 methyl 2 hydroxy 4 aminobenzene, at least one substance selected from the group consisting of 1 methyl 2,5 diaminobenzene, 1,4 diaminobenzene, 1,2,4 triaminobenzene, 1 methyl -2,5 diaminobenzene, 1,4 dimethyl 2,5 diaminobenzene, 1 methoxy 4- chloro 2,5 diaminobenzene, 1 methoxy- 4 methyl- 2, 5 diaminobenzene, 1 amino 4 hydroxy benzene, 1 amino 2 methyl 4 hydroxy benzene, 1 amino- 3 methyl 4 hydroxy benzene, 1,3 diamino 4- hydroxy benzene, and 4,4 diaminodiphenylamine, and an effective amount of an oxidizing agent therefor.
- a composition of matter for dyeing of hair which comprises substantially equimolar quantities of 1 methyl- 2 hydroxy 4 aminobenzene and of at least one substance selected from the group consisting of 1 methyl- 2,5 diaminobenzene, 1,4 diaminobenzene, 1,2,4 triaminobenzene, 1 methyl 2,5 diaminobenzene, 1,4- dimethyl 2,5 diaminobenzene, 1 methoxy 4 chloro- 2,5 diaminobenzene, 1 methoxy 4 methyl 2,5 diamino benzene, 1 amino 4 hydroxy benzene, 1- amino 2 methyl 4 hydroxy benzene, 1 amino 3- methyl 4 hydroxy benzene, 1,3 diamino 4 hydroxy benzene, and 4,4-diaminodiphenylamine, and an eifective amount of hydrogen peroxide as an oxidizing agent therefor.
- composition of matter for dyeing of hair which comprises 1-methyl-2-hydroxy-4-aminobenzene, at least one aromatic p-diamine adapted to form a hair dye upon oxidation, and an effective amount of an oxidizing agent therefor.
- a composition of matter for dyeing of hair which comprises 1-methyl-2-hydroxy-4-aminobenzene, at least one p-aminophenol adapted to form a hair dye upon oxidation, and an effective amount of an oxidizing agent therefor.
- a composition of matter for dyeing of hair which comprises a carrier substance compatible With hair and having distributed therethrough substantially equimolar quantities of 1-methyl-2-hydroxy-4-aminobenzene and of at least one substance selected from the group consisting of 1-methyl-2,S-diaminobenzene, 1,4-diaminobenzene, 1, 2,4 triaminobenzene, 1 methyl 2,5 diaminobenzene, 1,4-dimethyl 2,5 diaminobenzene, 1 methoxy 4- chloro 2,5 diaminobenzene, 1 methoxy 4 methyl- 2, 5 diaminobenzene, 1 amino 4 hydroxy benzene, 1 amino 2 methyl 4 hydroxy benzene, 1 amino- 3 methyl 4 hydroxy benzene, 1,3 diamino 4 hydroxy-benzene and 4,4-diaminodiphenylamine, and an effective amount of hydrogen peroxide as an oxidizing agent therefor.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DESCH30596A DE1143605B (de) | 1961-11-22 | 1961-11-22 | Mittel zum Faerben von lebenden Haaren |
Publications (1)
Publication Number | Publication Date |
---|---|
US3210252A true US3210252A (en) | 1965-10-05 |
Family
ID=7431807
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US240471A Expired - Lifetime US3210252A (en) | 1961-11-22 | 1962-11-23 | 1-methyl-2-hydroxy-4-aminobenzene as a modifier for oxidation dyes |
Country Status (4)
Country | Link |
---|---|
US (1) | US3210252A (fi) |
BE (1) | BE625116A (fi) |
DE (1) | DE1143605B (fi) |
GB (1) | GB973599A (fi) |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3413073A (en) * | 1965-04-21 | 1968-11-26 | Oreal | Substituted paradiamino-anisole and its use for dyeing human hair and keratinic fibers |
US3867094A (en) * | 1970-12-30 | 1975-02-18 | Oreal | Dyeing keratinous fibers with dye compositions containing indoanilines |
US3876368A (en) * | 1970-09-18 | 1975-04-08 | Oreal | Indamines for dyeing keratinic fibers |
US3884627A (en) * | 1971-10-04 | 1975-05-20 | Clairol Inc | Oxidative hair dye compositions |
US3898032A (en) * | 1971-06-11 | 1975-08-05 | Zotos Int Inc | Oxidative hair-coloring mixtures containing a conditioning agent |
US3899288A (en) * | 1971-12-02 | 1975-08-12 | Jean Galerne | Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid |
US3905761A (en) * | 1969-08-11 | 1975-09-16 | Oreal | Composition and method for dyeing keratinous fibers |
US3918896A (en) * | 1973-06-22 | 1975-11-11 | Oreal | Dye composition for keratinic fibers containing an oxidation base and a meta-aminophenol coupler |
US3929403A (en) * | 1969-06-11 | 1975-12-30 | Oreal | Process for producing indoanilines and keratin fiber dye composition containing the same |
US3931912A (en) * | 1971-08-12 | 1976-01-13 | The Gillette Company | Two-part hair dye or hair bleach package |
US3957424A (en) * | 1971-10-27 | 1976-05-18 | The Procter & Gamble Company | Enzyme-activated oxidative process for coloring hair |
US3970423A (en) * | 1971-10-04 | 1976-07-20 | Clairol Incorporated | Oxidative hair dye compositions |
US3981677A (en) * | 1974-01-02 | 1976-09-21 | Clairol Incorporated | Oxidative hair dye compositions containing N-substituted o-phenylenediamines and method for their use |
US4045170A (en) * | 1970-12-30 | 1977-08-30 | L'oreal | Hair dye composition containing an indoaniline |
US4065255A (en) * | 1975-06-26 | 1977-12-27 | L'oreal | 2-Methyl-5-N-hydroxyalkylaminophenol in an oxidation dye composition and method of using the same |
US4171203A (en) * | 1976-06-28 | 1979-10-16 | Henkel Kommanditgesellschaft Auf Aktien | Hair dye compositions containing 3,5-diamino-2-substituted-alkylbenzenes |
US5073173A (en) * | 1990-05-18 | 1991-12-17 | Clairol Incorporated | Dye couplers |
US5183941A (en) * | 1989-05-18 | 1993-02-02 | Clairol Incorporated | Hair dye coupler compounds |
EP0630642A1 (en) | 1993-05-17 | 1994-12-28 | Bristol-Myers Company | Naphthol couplers |
JPH0834716A (ja) * | 1994-01-24 | 1996-02-06 | L'oreal Sa | パラ−フェニレンジアミン誘導体および2−メチル−5−アミノフェノールを含有する、ケラチン繊維の酸化染色用組成物、および該組成物を用いる染色方法 |
US5514188A (en) * | 1993-07-13 | 1996-05-07 | L'oreal | Oxidation dye composition for keratinous fibres comprising a para-aminophenol, 2-methyl-5-aminophenol and a para-phenylenediamine and/or a bis(phenylalkylenediamine) |
US5693101A (en) * | 1993-12-22 | 1997-12-02 | L'oreal | Composition for the oxidation dyeing of keratinous fibres comprising a 3-fluoropara-aminophenol and at least one coupler selected from a meta-aminophenol and a meta-phenylenediamine and dyeing process using such a composition |
US5899212A (en) * | 1998-05-07 | 1999-05-04 | Novo Nordisk A/S | Re-formation of keratinous fibre cross links |
US5961666A (en) * | 1997-11-19 | 1999-10-05 | Lim; Mu-Ill | Hair dye compositions containing 3-substituted-4-aminophenols and 2-substituted-1-naphthols |
WO2014131579A1 (de) * | 2013-02-27 | 2014-09-04 | Henkel Ag & Co. Kgaa | Multitonale einschritt-färbungen i |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2833989A1 (de) * | 1978-08-03 | 1980-02-21 | Wella Ag | Mittel zum faerben von haaren |
FR2706297B1 (fr) * | 1993-06-16 | 1995-08-18 | Oreal | Composition de teinture d'oxydation des fibres kératiniques comprenant un paraaminophénol, un méta-aminophénol et un ortho-aminophénol, et procédé de teinture utilisant une telle composition. |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB805746A (en) * | 1955-11-18 | 1958-12-10 | Oreal | Improvements in or relating to the dyeing of animal fibres |
-
0
- BE BE625116D patent/BE625116A/xx unknown
-
1961
- 1961-11-22 DE DESCH30596A patent/DE1143605B/de active Pending
-
1962
- 1962-10-17 GB GB39324/62A patent/GB973599A/en not_active Expired
- 1962-11-23 US US240471A patent/US3210252A/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB805746A (en) * | 1955-11-18 | 1958-12-10 | Oreal | Improvements in or relating to the dyeing of animal fibres |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3413073A (en) * | 1965-04-21 | 1968-11-26 | Oreal | Substituted paradiamino-anisole and its use for dyeing human hair and keratinic fibers |
US3929403A (en) * | 1969-06-11 | 1975-12-30 | Oreal | Process for producing indoanilines and keratin fiber dye composition containing the same |
US3905761A (en) * | 1969-08-11 | 1975-09-16 | Oreal | Composition and method for dyeing keratinous fibers |
US3876368A (en) * | 1970-09-18 | 1975-04-08 | Oreal | Indamines for dyeing keratinic fibers |
US3867094A (en) * | 1970-12-30 | 1975-02-18 | Oreal | Dyeing keratinous fibers with dye compositions containing indoanilines |
US4045170A (en) * | 1970-12-30 | 1977-08-30 | L'oreal | Hair dye composition containing an indoaniline |
US3898032A (en) * | 1971-06-11 | 1975-08-05 | Zotos Int Inc | Oxidative hair-coloring mixtures containing a conditioning agent |
US3931912A (en) * | 1971-08-12 | 1976-01-13 | The Gillette Company | Two-part hair dye or hair bleach package |
US3970423A (en) * | 1971-10-04 | 1976-07-20 | Clairol Incorporated | Oxidative hair dye compositions |
US3884627A (en) * | 1971-10-04 | 1975-05-20 | Clairol Inc | Oxidative hair dye compositions |
US3957424A (en) * | 1971-10-27 | 1976-05-18 | The Procter & Gamble Company | Enzyme-activated oxidative process for coloring hair |
US3899288A (en) * | 1971-12-02 | 1975-08-12 | Jean Galerne | Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid |
US3918896A (en) * | 1973-06-22 | 1975-11-11 | Oreal | Dye composition for keratinic fibers containing an oxidation base and a meta-aminophenol coupler |
US3981677A (en) * | 1974-01-02 | 1976-09-21 | Clairol Incorporated | Oxidative hair dye compositions containing N-substituted o-phenylenediamines and method for their use |
US4065255A (en) * | 1975-06-26 | 1977-12-27 | L'oreal | 2-Methyl-5-N-hydroxyalkylaminophenol in an oxidation dye composition and method of using the same |
US4171203A (en) * | 1976-06-28 | 1979-10-16 | Henkel Kommanditgesellschaft Auf Aktien | Hair dye compositions containing 3,5-diamino-2-substituted-alkylbenzenes |
US5183941A (en) * | 1989-05-18 | 1993-02-02 | Clairol Incorporated | Hair dye coupler compounds |
US5073173A (en) * | 1990-05-18 | 1991-12-17 | Clairol Incorporated | Dye couplers |
EP0630642A1 (en) | 1993-05-17 | 1994-12-28 | Bristol-Myers Company | Naphthol couplers |
US5514188A (en) * | 1993-07-13 | 1996-05-07 | L'oreal | Oxidation dye composition for keratinous fibres comprising a para-aminophenol, 2-methyl-5-aminophenol and a para-phenylenediamine and/or a bis(phenylalkylenediamine) |
US5693101A (en) * | 1993-12-22 | 1997-12-02 | L'oreal | Composition for the oxidation dyeing of keratinous fibres comprising a 3-fluoropara-aminophenol and at least one coupler selected from a meta-aminophenol and a meta-phenylenediamine and dyeing process using such a composition |
JPH0834716A (ja) * | 1994-01-24 | 1996-02-06 | L'oreal Sa | パラ−フェニレンジアミン誘導体および2−メチル−5−アミノフェノールを含有する、ケラチン繊維の酸化染色用組成物、および該組成物を用いる染色方法 |
US5961666A (en) * | 1997-11-19 | 1999-10-05 | Lim; Mu-Ill | Hair dye compositions containing 3-substituted-4-aminophenols and 2-substituted-1-naphthols |
US5899212A (en) * | 1998-05-07 | 1999-05-04 | Novo Nordisk A/S | Re-formation of keratinous fibre cross links |
WO2014131579A1 (de) * | 2013-02-27 | 2014-09-04 | Henkel Ag & Co. Kgaa | Multitonale einschritt-färbungen i |
US9402795B2 (en) | 2013-02-27 | 2016-08-02 | Henkel Ag & Co. Kgaa | Multi-tonal one-step dyes |
Also Published As
Publication number | Publication date |
---|---|
BE625116A (fi) | |
GB973599A (en) | 1964-10-28 |
DE1143605B (de) | 1963-02-14 |
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