US2162458A - Hair dye - Google Patents
Hair dye Download PDFInfo
- Publication number
- US2162458A US2162458A US140689A US14068937A US2162458A US 2162458 A US2162458 A US 2162458A US 140689 A US140689 A US 140689A US 14068937 A US14068937 A US 14068937A US 2162458 A US2162458 A US 2162458A
- Authority
- US
- United States
- Prior art keywords
- hair
- hair dye
- compounds
- dye
- stands
- 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
- 239000000118 hair dye Substances 0.000 title description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 5
- -1 hydroxy- Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 244000208060 Lawsonia inermis Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000479 mixture part Substances 0.000 description 1
- NCIAGQNZQHYKGR-UHFFFAOYSA-N naphthalene-1,2,3-triol Chemical compound C1=CC=C2C(O)=C(O)C(O)=CC2=C1 NCIAGQNZQHYKGR-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
Definitions
- This invention is based on the observation that 1.2.4-trihydroxy-compounds of benzene and naphthalene, if desired containing alkyl-, hydroxyalkyl and 'alkoxy-groups as substituents,
- hair dyes of blond to titian red may be obtained.
- lighter and darker tints may be obtained so that by suitable mixtures all dyeings from the lightestblond to black may be produced.
- the oxidation may be left to the action of the air or there may be added to the dye bath hydrogen peroxide, asis known 15 practice in dyeing pelts.
- the hair dyes obtained are of good fastness, particularly to rubbing.
- cation may be included.
- Example 1 --1.5 grams of 1.2.4-triacetylhydroxynaphthalene are saponifled in 10 cc. 0i 8 l 25 cohol and 20 cc. of water with'2 grams of calcined sodium carbonate at boiling temperature. The solution is cooled to about 30 0. and the well degreased grey hair is brushed with it. After a short time the hair is rinsed, soaped and dried; 30 it then exhibits a titian red color.
- Example 2 -'-1 gram of 1.2.4-triacetylhydroxynaphthalene and 0.5 gram of 1.2.4-triacetylhydroxybenzene are saponifled in 10 cc. of alcohol and 20 cc. of water with'2 grams of calcined sodium carbonate at the boiling point of the mixture. When the solution is cooled to 30 C. and 0.5 cc.
- Example 3 A mixture of 1 gram of 1.2.4- triacetylhydropynaphthalene and 1 gram of 1.2.4- triacetylhydroxy-benzene and 0.5 gram of paraamino-diphenylamine is dissolved in 10 cc. of alcohol and 20 cc. of water and the solution is I boiled for a short time after addition of 2 grams of calcined sodium carbonate. The solution cooled to about 301 C. is mixed with 2 cc. 011a solution of ferrous ammonium sulfate 01' 10 per stituents necessary for shading and for saponiflg0- compressed to shape:
- Example 4 Form making tablets the following substances are mixed together and the mixture Parts 1.2.4-triacetyflhydroxynaphthalene 50' 1.2.btriacetylhydroxybenzene 15 Starch 5 Dosdtxine 5- Urea e 5 The sodium salt of an N-butylated naphtha- 16ll8-a-Slllf0nic acid The hair dye thus made dyes grey hair redblond.
- droxyethylor alkoxy-group in the nucleus may be used in the same manner.
- a hair dye comprising the triacetyl com pound of the general formula l 0.00.011; (1 IR-O.CO:CH: (2) o.oo.cm (4 wherein R stands for a radicle oi the group consisting of phenyl and naphthyl and :1: stands for a member of the group consisting of hydrogen, methyl, ethyl and hydroxyethyl.
- a hair dye comprising the triacetyl compound of the general formula O.CO.CO
- :1 stands for a member of the group consisting of hydrogen, methyl, ethyl, and hydroxyethyl.
- V t stands for a member of the group consisting of hydrogen, methyl, ethyl, and hydroxyethyl.
- a hair dye comprising 1,2,4-trlaLcetylhydroxynaphthalene.
- R stands for a radicle of the group consisting of phenyl and naphthyl and :t'stands for a member of the group consisting of hydrogen, methyl, ethyl and hydroxyethyl, and sodium carbonate.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Description
Patented 'June-13, 1939 UNITED STATES PATENTIOFFICE HAIR DYE -No Drawing.
6 Claims.
' preparation for dyeing living hair, which can be stored for a long time without decomposition and in a form in which it is not oxidized by the air, but from which itcan be easily transformed into -.the active form which is oxidizable on the hair without use of an oxidizing agent or a metal mo'rdant.
Further objects of my invention will be seen' from the detailed specification following here-- after.
For dyeing living hair in addition to natural substances like henna and reng, the so-called Persian hair dye, synthetic substances have come into usein increasing degree. The latter include chiefly the hydroxy-, amino hydroxyand diamino-compounds of the aromatic series, for instance, pyrogallol, para-aminophenol, para-toluylene diamine, para-amino-diphenylami'ne and naphthylene diamine. On account of its strong toxic action para-phenylene diamine is forbidden missible substances of this kind cause more or less considerable irritation of the skin ofespecially sensitive individuals and attempts have been made in various ways to rob such compounds of their injurious eifect. The sensitivity of individuals, however, is so various that it cannot be asserted that this or that compound will have no irritating effect on the human skin.
This invention is based on the observation that 1.2.4-trihydroxy-compounds of benzene and naphthalene, if desired containing alkyl-, hydroxyalkyl and 'alkoxy-groups as substituents,
are surprisingly suitable for dyeing living hair.
On 'account of their insuillcient durability they are advantageously used in the form of their triacyl-compounds and in this form employed for preparation of the dye-bath. By the addition of an alkaline agent, such as sodium carbonate, ammonia, a phosphate or the like they are saponified to the'trihydroxy-compounds. These, under the influence of atmospheric oxygen, are converted on the hair into compounds resembling quinone; thus for example, from 1.2.4-hydroxynaphthalene the 2-hydroxy-L4-naphthoquinone Application May 4, 1937, Serial 140,689. 'In Germany May 8, 1936 for use in most countries. However, other peris formed which is the compound present in henna.
With compounds of the said kind hair dyes of blond to titian red may be obtained. By shading with known synthetic substances of the above 5 -kind lighter and darker tints may be obtained so that by suitable mixtures all dyeings from the lightestblond to black may be produced.
' An addition of a small proportion of a metal salt, for example a salt of iron, copper, cobalt or 10 nickel, to the dye bath hastens the absorption of ,the oxidationdye and, within certain limits, in-
fluenees the color tint- The oxidation may be left to the action of the air or there may be added to the dye bath hydrogen peroxide, asis known 15 practice in dyeing pelts. The hair dyes obtained are of good fastness, particularly to rubbing.
In making up the new hair dyes to tablet form, which makes possible an accurate dose, the con,-
cation may be included. a
. The following examples illustrate the invention:
Example 1.--1.5 grams of 1.2.4-triacetylhydroxynaphthalene are saponifled in 10 cc. 0i 8 l 25 cohol and 20 cc. of water with'2 grams of calcined sodium carbonate at boiling temperature. The solution is cooled to about 30 0. and the well degreased grey hair is brushed with it. After a short time the hair is rinsed, soaped and dried; 30 it then exhibits a titian red color.
Example 2.-'-1 gram of 1.2.4-triacetylhydroxynaphthalene and 0.5 gram of 1.2.4-triacetylhydroxybenzene are saponifled in 10 cc. of alcohol and 20 cc. of water with'2 grams of calcined sodium carbonate at the boiling point of the mixture. When the solution is cooled to 30 C. and 0.5 cc.
of hydrogen peroxide of 30 per cent.strength has been added it is brushed into the'well degreased. grey hair. After a short time the hair is rinsed, 40 soaped and dried; it exhibits a full blond.
Example 3.-A mixture of 1 gram of 1.2.4- triacetylhydropynaphthalene and 1 gram of 1.2.4- triacetylhydroxy-benzene and 0.5 gram of paraamino-diphenylamine is dissolved in 10 cc. of alcohol and 20 cc. of water and the solution is I boiled for a short time after addition of 2 grams of calcined sodium carbonate. The solution cooled to about 301 C. is mixed with 2 cc. 011a solution of ferrous ammonium sulfate 01' 10 per stituents necessary for shading and for saponiflg0- compressed to shape:
' greased grey hair.
cent. strength and then brushed on the well de- After a short time the hair is rinsed, soaped and dried; it exhibits a full black.
Example 4. -For making tablets the following substances are mixed together and the mixture Parts 1.2.4-triacetyflhydroxynaphthalene 50' 1.2.btriacetylhydroxybenzene 15 Starch 5 Dosdtxine 5- Urea e 5 The sodium salt of an N-butylated naphtha- 16ll8-a-Slllf0nic acid The hair dye thus made dyes grey hair redblond.
'A wetting agent made asdescribed in German specification No. 538,762 and made by treating castor oil with l-naphthyl-5- sulfonic acid in presence of sulfuric acid 42 are mil red together and moulded to tablets. This hair dye dyes grey hair brown.
It is obvious that my invention is not limited to the foregoing examples or to the specific details given therein. Thus, for instance, I have chosen in the examples the triaeetylhydroxy compounds. Obviously, in the same manner other acyl compounds of the trihydroxynaphthalene or -benzene may be used. 'On the other hand, such compounds bearing a. methyl-, ethyl-, hy-
droxyethylor alkoxy-group in the nucleus may be used in the same manner.
' What! claim is:
1. ;A hair dye comprising the triacetyl com pound of the general formula l 0.00.011; (1 IR-O.CO:CH: (2) o.oo.cm (4 wherein R stands for a radicle oi the group consisting of phenyl and naphthyl and :1: stands for a member of the group consisting of hydrogen, methyl, ethyl and hydroxyethyl.
2. A hair dye comprising the triacetyl compound of the general formula O.CO.CO|
.CO.CH:
wherein :1: stands for a member of the group consisting of hydrogen, methyl, ethyl, and hydroxyethyl. V t
3. A hair dye comprising 1,2,4-trlaLcetylhydroxynaphthalene.
4. A hair dye preparation containing the triacetyl compound of the general formula wherein R stands for a radicle of the group consisting of phenyl and naphthyl and 1: stands for a member of the group consisting of hydrogen, methyl, ethyl and hydroxyethyl, and an alkaline agent capable of saponifying the acetyl groups when the preparation is dissolved in water and boiled.
5. A hair dye preparation containing the triacetyl compound of the general formula .tR-O.C O.CH3 (2) O.CO.CH: (4)
wherein R stands for a radicle of the group consisting of phenyl and naphthyl and :t'stands for a member of the group consisting of hydrogen, methyl, ethyl and hydroxyethyl, and sodium carbonate.
-6. A hair dye preparation containing 1,2,4-
bonate. ERICH LEHIMANN.
I triacetyl hydroxynaphthalene and sodium car-
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE493855X | 1936-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2162458A true US2162458A (en) | 1939-06-13 |
Family
ID=6544630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US140689A Expired - Lifetime US2162458A (en) | 1936-05-08 | 1937-05-04 | Hair dye |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2162458A (en) |
| FR (1) | FR826046A (en) |
| GB (1) | GB493855A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2695259A (en) * | 1949-01-03 | 1954-11-23 | Union Francaise Commerciale Et Industrielle Sa | Dermatologically harmless hair dyeing creams |
| US2733186A (en) * | 1951-04-19 | 1956-01-31 | Compositions for the dyeing of hair | |
| US2875769A (en) * | 1957-08-20 | 1959-03-03 | Apod Corp | Keratinaceous fiber dye of hydroquinone and either dihydroxyphenylalanine or dihydroxyphenylglycine and method of its use |
| DE1083505B (en) * | 1955-07-29 | 1960-06-15 | Monsavon L Oreal Sa Francaise | Methods and means for coloring hair |
| US3164522A (en) * | 1960-05-17 | 1965-01-05 | Oreal | Method of using diphenylazo compounds as direct dyes in alkaline media on human hair |
| US3231471A (en) * | 1961-11-09 | 1966-01-25 | Hans Schwarzkopf | 2, 6-dioxypyridine and acid addition salts thereof for dyeing human hair |
| US3904357A (en) * | 1972-10-30 | 1975-09-09 | Avon Prod Inc | Means for promoting color change in bleached or untreated hair |
| US3920384A (en) * | 1974-07-17 | 1975-11-18 | Clairol Inc | Autoxidizable hair dye containing preparations |
| US3970423A (en) * | 1971-10-04 | 1976-07-20 | Clairol Incorporated | Oxidative hair dye compositions |
| US4054413A (en) * | 1974-07-17 | 1977-10-18 | Clairol Incorporated | Autoxidizable hair dye containing preparations |
| US4212645A (en) * | 1974-01-18 | 1980-07-15 | Lever Brothers Company | Hair dyeing composition containing an aryldiamine and a substituted catechol |
| US4992077A (en) * | 1986-08-21 | 1991-02-12 | Goldwell Gmbh | Agent for the oxidative dyeing of hair, method for the preparation of the agent and use of the agent |
| US5529583A (en) * | 1995-09-14 | 1996-06-25 | Clairol Incorporated | Storage stable 2-methyl-1-naphthol couplers |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE968627C (en) * | 1954-04-23 | 1958-03-13 | Hans Pichlmayr Dr Ing | Process for the preparation of an agent for bleaching or coloring hair |
-
1937
- 1937-04-08 FR FR826046D patent/FR826046A/en not_active Expired
- 1937-04-15 GB GB10748/37A patent/GB493855A/en not_active Expired
- 1937-05-04 US US140689A patent/US2162458A/en not_active Expired - Lifetime
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2695259A (en) * | 1949-01-03 | 1954-11-23 | Union Francaise Commerciale Et Industrielle Sa | Dermatologically harmless hair dyeing creams |
| US2733186A (en) * | 1951-04-19 | 1956-01-31 | Compositions for the dyeing of hair | |
| DE1083505B (en) * | 1955-07-29 | 1960-06-15 | Monsavon L Oreal Sa Francaise | Methods and means for coloring hair |
| US2875769A (en) * | 1957-08-20 | 1959-03-03 | Apod Corp | Keratinaceous fiber dye of hydroquinone and either dihydroxyphenylalanine or dihydroxyphenylglycine and method of its use |
| US3164522A (en) * | 1960-05-17 | 1965-01-05 | Oreal | Method of using diphenylazo compounds as direct dyes in alkaline media on human hair |
| US3231471A (en) * | 1961-11-09 | 1966-01-25 | Hans Schwarzkopf | 2, 6-dioxypyridine and acid addition salts thereof for dyeing human hair |
| US3970423A (en) * | 1971-10-04 | 1976-07-20 | Clairol Incorporated | Oxidative hair dye compositions |
| US3904357A (en) * | 1972-10-30 | 1975-09-09 | Avon Prod Inc | Means for promoting color change in bleached or untreated hair |
| US4212645A (en) * | 1974-01-18 | 1980-07-15 | Lever Brothers Company | Hair dyeing composition containing an aryldiamine and a substituted catechol |
| US3920384A (en) * | 1974-07-17 | 1975-11-18 | Clairol Inc | Autoxidizable hair dye containing preparations |
| US4054413A (en) * | 1974-07-17 | 1977-10-18 | Clairol Incorporated | Autoxidizable hair dye containing preparations |
| US4992077A (en) * | 1986-08-21 | 1991-02-12 | Goldwell Gmbh | Agent for the oxidative dyeing of hair, method for the preparation of the agent and use of the agent |
| US5529583A (en) * | 1995-09-14 | 1996-06-25 | Clairol Incorporated | Storage stable 2-methyl-1-naphthol couplers |
| US5672180A (en) * | 1995-09-14 | 1997-09-30 | Clairol Incorporated | Storage stable 2-methyl-1-naphthol couplers |
| US6045590A (en) * | 1995-09-14 | 2000-04-04 | Bristol-Myers Squibb Co. | Storage stable 2-methyl-1-naphthol couplers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB493855A (en) | 1938-10-17 |
| FR826046A (en) | 1938-03-21 |
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