US3359168A - Dyeing hair with 2, 3, 6-triaminopyridine and salts thereof - Google Patents
Dyeing hair with 2, 3, 6-triaminopyridine and salts thereof Download PDFInfo
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- US3359168A US3359168A US569851A US56985166A US3359168A US 3359168 A US3359168 A US 3359168A US 569851 A US569851 A US 569851A US 56985166 A US56985166 A US 56985166A US 3359168 A US3359168 A US 3359168A
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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
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- 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
Definitions
- aminobenzenes such as m-diaminobenzenes or derivatives thereof must be combined with other amines such as oor p-diaminobenzenes and on oxidation with a suitable'oxidizing agent such ashydrogen peroxide, urea peroxide, sodium borate and the like, the combination yields a blue color; 2,6-diaminop'y'ridines or substituted 2, 6-diaminopyridines must be combined with aminobenzenes to give a blue color on oxidation.
- these novel and highly desirable results are attained by treating hair with a comp sition containing 2,3,6-triaminopyridine in amounts described below and in the presence of a suitable oxidizing agent.
- the intensity of coloration produced on hair is in direct proportion to and dependent upon the concentration of 2,3,6-triaminopyridine employed.
- a satisfactory greenish-blue color may be obtained by applying to the hair a composition containing about 0.01% to 2.0% by weight of 2,3,6-triaminopyridine and then oxidizing the dye in said composition in situ.
- the 2,3,6-triaminopyridine used in this composition is prepared by catalytically reducing 3-phenylazo-2,6-diaminopyridine in the presence of hydrochloric acid as described below in Example 1.
- the 2,3,6-triaminopyridine may be employed in the form of its acid addition salts, such as 2,3,6-triaminopyridine dihydrochloride, 2,3,6-triaminopyridine sulfate and other suitable salts.
- Such salts are readily prepared by the usual methods, such as, for example, the reaction of a stoichiometrically equivalent amount of the base and the desired acid in an inert common solvent.
- acids which are suitable for the preparation of acid addition salts of the amine base of this invention are inorganic acids, such as, for example, hydrochloric, nitric, sulfuric, phosphoric, and the like acids, and organic acids, such as, as for example, benzoic, acetic, salicyclic, maleic, tartaric, citric and the like acids.
- the 2,3,6-triaminopyridine in the form of its free base or in the form of its acid addition salts may then be dissolved in water and used as such or they may also be dissolved in a suitable vehicle for carrying hair dyes such as those described by Kass in American Perfumer and Aromatics, vol. 68, No. 1, pp. 25-28, July 1956.
- suitable vehicles are those that contain ammonium oleate, fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, fatty amines, ethoxylated fatty amines, phosphate esters and the like.
- These vehicles may optionally contain wetting agents such as the condensation product of fatty acids containing 6 to 20 carbon atoms with diethanolamine or monoethanolamine, the condensation product of the methyl esters of fatty acids with diethanolamine or monoethanolamine.
- fatty acids used in the above description includes acids such as capric, lauric, myristic, palmitic, stearic, linoleic, oleic, ricinoleic, linolenic or mixtures of fatty acids occurring in natural fats and oils such as tallow, cocoanut oil, castor oil and the like.
- fatty alcohols used in the above description includes alcohol such as lauryl alcohol, oleyl alcohol, myristy-l alcohol, cetyl alcohol, stearyl alcohol, alcohols extracted from lanolin and the like, and'mixtures thereof.
- the active ingredient may be present in amounts of from about 0.01 to 2.0% by weight.
- the final solution may have a pH value of about 8 to 11 and this may be achieved by the addition of a base such as ammonium hydroxide.
- the user For use the user combines the solution containing the active ingredient with about 1 to 2 parts by volume or by weight of a suitable oxidizing agent such as urea peroxide, hydrogen peroxide, sodium borate and the like.
- a suitable oxidizing agent such as urea peroxide, hydrogen peroxide, sodium borate and the like.
- the choice of the oxidizing agent is not critical and other conventional oxidizing agents useful in hair bleaching may also be used.
- the amine oxidizing agent mixture is then applied to hair desired to be dyed. The solution is allowed to remain in contact with the hair for about 10 to 30 minutes. The hair is then shampooed and after drying is found to assume the new shade.
- 2,3,6-triaminopyridine if desired may also be combined with other amines such as those disclosed in US. Patent No. 3,200,040 or diaminobenzenes or combinations thereof to give other hair coloring compositions.
- 0.01% to 2.0% by weight of 2,3,6-triaminopyridine may be combined with 0.01% to 2% by weight of o-, mor p-diaminobenzenes or combinations of o-, mor p-diaminobenzenes to give other colorations.
- diaminobenzenes instead of using diaminobenzenes in these combinations we have found o-, mor p-diaminopyridines may be used.
- Example 1 Preparation of 2,3,6-triaminopyridine
- a suspension of 124.5 g. (0.5 mole) of 3-phenylazo- 2,6-diaminopyridine in 500 m1. of water and 200 ml. of 37% HCl is reduced in a Parr hydrogenator in the presence of 0.4 g. of 5% Pd on carbon catalyst. The reduction proceeds rapidly to completion at 20 to 30 C.
- the catalyst is filtered at once before the product can precipi tate and the colorless filtrate is diluted with an equal volume of isopropanol. After standing in the cold for several hours the dihydrochloride precipitates as transparent colorless prisms and is filtered, washed with isopropanol and dried to constant weight in vacuo.
- the first crop weighs 41 g. and melts with decomposition starting about 230 C.
- a second crop can be obtained by concentration of the filtrate to give a total yield of about 70% of theory.
- the material can be further purified by dissolving in a small quantity of water and precipitating with excess HCl.
- compositions of the following Examples 2 to 7 are prepared by simple mixing procedures.
- Example 9 In order to use these compositions to impart the de sired shade to human hair one part of the selected composition is mixed with approximately 1 to 2 parts of 6% hydrogen peroxide solution.
- the resulting solution is then applied to white hair and allowed to remain in contact with the treated hair for about half an hour after which the hair is rinsed and shampooed. After drying the hair assumes the shade as described.
- Process for imparting a greenish-blue coloration to hair which comprises contacting hair with an aqueous solution of about 0.01% to 2% by weight of 2,3,6-triaminopyridine or the salts of 2,3,6-triaminopyridine in the presence of an oxidizing agent.
- Process for imparting a greenish-blue coloration to hair which comprises. contacting said hair with an aqueous solution containing about 0.01% to 2% by weight of 2,3,6-triaminopyridine or the salts of 2,3,-6-triaminopyridine in the presence of a hydrogen peroxide solution.
- a composition for dyeing hair which comprises as active ingredient of about 0.01% to 2% by weight of 2,3,6-triaminopyridine or the salts of 2,3,6-triaminopyridine in an aqueous solvent.
- a composition for dyeing hair which comprises as active ingredient of about 0.01% to 2% by weight of 2,3,6-triaminopyridine or the salts of 2,3,6-triaminopyridine and about 0.01% to 2% by weight of 2,6-diaminopyridine.
- a composition for dyeing hair which comprises as active ingredients about 0.01 to 2.0% by weight of 2,3,6- triaminopyridine and 0.01% to 2.0% of o-, m-, or p-diaminobenzenes or combinations thereof.
- a method for dyeing hair which comprises contacting hair with a composition in accordance with claim 5 in the presence of an oxidizing agent.
- Cited ggigilizriilieifiglliite is hydrogen peroxide, urea peroxide or UNITED STATES PATENTS 8.
- a composition for dyeing hair which comprises as 3,200,040 8/1965 Lange at 167 88 active ingredients of about 0.01 to 2.0% by weight of 5 2,3,6-triaminopyridine and 0.01% to 2.0% of 0-, m-, or ALBERT MEYERS Prlmary Exammer' p-diaminopyridines. VERA C. CLARKE, Assistant Examiner.
Description
United States Patent 3,359,168 DYEING HAIR WITH 2,3,6-TRIAMINOPYRIDINE AND SALTS THEREOF Stanley Brechner, West Orange, and Leonard A. Como, Franklin Boro, N.J., assignors to Warner-Lambert Pharmaceutical Company, Morris Plains, N.J., a corporation of Delaware No Drawing. Filed Aug. 3, 1966, Ser. No. 569,851 8 Claims. (Cl. 167-88) The present invention relates to a method employing novel compositions comprising 2,3,6-triaminopyridine or its salts for dyeing hair to impart a greenish-blue color thereto as well as to compositions combining said 2,3,6- triaminopyridine together with other dyes to give other shades.
It is known in the art that in order to produce bluish or greenish-blue shades when dyeing hair with amine dyes, one must employ at least two separate oxidizable amines. For example, aminobenzenes such as m-diaminobenzenes or derivatives thereof must be combined with other amines such as oor p-diaminobenzenes and on oxidation with a suitable'oxidizing agent such ashydrogen peroxide, urea peroxide, sodium borate and the like, the combination yields a blue color; 2,6-diaminop'y'ridines or substituted 2, 6-diaminopyridines must be combined with aminobenzenes to give a blue color on oxidation. For example, US. Patent No. 3,200,040 discloses that 2,6-diaminopyridine or substituted 2,6-diaminopyr'idine's in combination with certain diaminobenzenes or aminophenols will produce a blue color on treatment with oxidizing agents. The 2,6- diaminopyridine alone produces only a pale yellow color. Accordingly, combination products were the only products available heretofore if it were desired to impart a blue shade to the hair employing oxidizable amines. We have now found that a greenish-blue color may be imparted to hair-by oxidation employing but a single oxidizable amine. Accordingly, we provide novel compositions of matter containing but a single oxidizable amine which when treated with an oxidizing agent yields a greenishblue dye which may be used to dye hair with a remarkable degree of consistency where the intensity of coloration imparted to hair is not only controllable but reproducible time after time.
In accordance with this invention, these novel and highly desirable results are attained by treating hair with a comp sition containing 2,3,6-triaminopyridine in amounts described below and in the presence of a suitable oxidizing agent. The intensity of coloration produced on hair is in direct proportion to and dependent upon the concentration of 2,3,6-triaminopyridine employed. Generally speaking, a satisfactory greenish-blue color may be obtained by applying to the hair a composition containing about 0.01% to 2.0% by weight of 2,3,6-triaminopyridine and then oxidizing the dye in said composition in situ.
The 2,3,6-triaminopyridine used in this composition is prepared by catalytically reducing 3-phenylazo-2,6-diaminopyridine in the presence of hydrochloric acid as described below in Example 1.
The 2,3,6-triaminopyridine may be employed in the form of its acid addition salts, such as 2,3,6-triaminopyridine dihydrochloride, 2,3,6-triaminopyridine sulfate and other suitable salts.
Such salts are readily prepared by the usual methods, such as, for example, the reaction of a stoichiometrically equivalent amount of the base and the desired acid in an inert common solvent. Examples of acids which are suitable for the preparation of acid addition salts of the amine base of this invention are inorganic acids, such as, for example, hydrochloric, nitric, sulfuric, phosphoric, and the like acids, and organic acids, such as, as for example, benzoic, acetic, salicyclic, maleic, tartaric, citric and the like acids.
The 2,3,6-triaminopyridine in the form of its free base or in the form of its acid addition salts may then be dissolved in water and used as such or they may also be dissolved in a suitable vehicle for carrying hair dyes such as those described by Kass in American Perfumer and Aromatics, vol. 68, No. 1, pp. 25-28, July 1956. Examples of such vehicles are those that contain ammonium oleate, fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, fatty amines, ethoxylated fatty amines, phosphate esters and the like. These vehicles may optionally contain wetting agents such as the condensation product of fatty acids containing 6 to 20 carbon atoms with diethanolamine or monoethanolamine, the condensation product of the methyl esters of fatty acids with diethanolamine or monoethanolamine. The term fatty acids used in the above description includes acids such as capric, lauric, myristic, palmitic, stearic, linoleic, oleic, ricinoleic, linolenic or mixtures of fatty acids occurring in natural fats and oils such as tallow, cocoanut oil, castor oil and the like.
The term fatty alcohols used in the above description includes alcohol such as lauryl alcohol, oleyl alcohol, myristy-l alcohol, cetyl alcohol, stearyl alcohol, alcohols extracted from lanolin and the like, and'mixtures thereof.
The active ingredient may be present in amounts of from about 0.01 to 2.0% by weight. The final solution may have a pH value of about 8 to 11 and this may be achieved by the addition of a base such as ammonium hydroxide. I
For use the user combines the solution containing the active ingredient with about 1 to 2 parts by volume or by weight of a suitable oxidizing agent such as urea peroxide, hydrogen peroxide, sodium borate and the like. The choice of the oxidizing agent is not critical and other conventional oxidizing agents useful in hair bleaching may also be used. The amine oxidizing agent mixture is then applied to hair desired to be dyed. The solution is allowed to remain in contact with the hair for about 10 to 30 minutes. The hair is then shampooed and after drying is found to assume the new shade.
We have found that 2,3,6-triaminopyridine if desired may also be combined with other amines such as those disclosed in US. Patent No. 3,200,040 or diaminobenzenes or combinations thereof to give other hair coloring compositions.
For example, 0.01% to 2.0% by weight of 2,3,6-triaminopyridine may be combined with 0.01% to 2% by weight of o-, mor p-diaminobenzenes or combinations of o-, mor p-diaminobenzenes to give other colorations. Instead of using diaminobenzenes in these combinations we have found o-, mor p-diaminopyridines may be used.
The following examples are included. in order to further illustrate the invention.
Example 1.Preparation of 2,3,6-triaminopyridine A suspension of 124.5 g. (0.5 mole) of 3-phenylazo- 2,6-diaminopyridine in 500 m1. of water and 200 ml. of 37% HCl is reduced in a Parr hydrogenator in the presence of 0.4 g. of 5% Pd on carbon catalyst. The reduction proceeds rapidly to completion at 20 to 30 C. The catalyst is filtered at once before the product can precipi tate and the colorless filtrate is diluted with an equal volume of isopropanol. After standing in the cold for several hours the dihydrochloride precipitates as transparent colorless prisms and is filtered, washed with isopropanol and dried to constant weight in vacuo. The first crop weighs 41 g. and melts with decomposition starting about 230 C. A second crop can be obtained by concentration of the filtrate to give a total yield of about 70% of theory.
3 If necessary, the material can be further purified by dissolving in a small quantity of water and precipitating with excess HCl.
The compositions of the following Examples 2 to 7 are prepared by simple mixing procedures.
Example 2 Greenish-blue coloration:
2,3, 6-triaminopyridine dihydrochloride percent by weight 0.02 The condensation product of 10 moles of ethylene oxide and nonyl phenol do 20.0 Sodium sulfite (as antioxidant) do 0.25 Sufficient ammonia solution to yield a solution having a pH 9. Distilled water to make percent by volume 100.00
Example 3 Light warm brown coloration:
Ammonium oleate percent by weight 20.00 p-phenylenediamine do 0.25 2,3,6-triaminopyridine dihydrochloride do 0.15 Anti-oxidant (sodium sulfite) do 1.00 Ammonia (2 8%) to adjust the pH to 9.5. Distilled water to make percent by volume 100.00
Example 4 Dark ash brown coloration:
Laurie diethanolamine percent by weight 3.00 Ammonium oleate do 2.50 p-phenylenediamine do 0.25 2,3,6-triamin0pyridine dihydrochloride do 0.25 Anti-oxidant (sodium sulfite) do 1.00 Ammonia (28%) to pH 9.5. Distilled water to make percent by volume 100.00
Example 5 Dark blue-black coloration:
Cocoanut monoethanolamide percent by weight 2.00 Propylene glycol do 6.00 p-phenylenediamine do 0.85 2,3,6-triaminopyridine dihydrochloride do 1.10 Anti-oxidant do 1.00 Ammonia (28%) to pH 9.5. Distilled water to make percent by volume 100.00
Example 6 Orange red coloration:
Triethanolamine lauryl sulfate percent by weight 20.00 2,5-diaminopyridine dihydrochloride do 0.50 2,3,6-triaminopyridine dihydro chloride do 0.05 Anti-oxidant do 0.25 Ammonia (28%) to pH 9.0. Distilled water to make percent by volume 100.00
Example 7 Lightwarm brown coloration:
Ammonium oleate percent by Weight 20.00 2,5-diaminopyridine dihydrochloride do 0.45
4 2,3,6-triaminopyridine dihydrochloride do 0.025 Anti-oxidant do 0.25 Ammonia (28%) to pH 9.0. Distilled water to make percent by volume 100.00
Example 7.4
Diester of phosphoric acid and oleic acid percent by weight 5.00 Monoester of phosphoric acid and oleic acid do 5.00 2,5-diaminopyridine dihydrochloride do 0.40 2,3,6-triaminopyridine dihydrochloride monohydrate do 0.06 Anti-oxidant do 0.25 Ammonia (28%) to pH 9.0. Distilled water to make percent by volume 100.00
Example 8 Medium ash brown coloration:
The condensation product of 10 moles of ethylene oxide and nonyl phenol percent by weight" 20.00 2,54iiaminopyridine dihydrochloride -do 0.40 2,3,6-triaminopyridine dihydrochloride do- 0.05 Anti-oxidant -do 0.25 Ammonia (28%) to pH 9.0. Distilled water to make percent by volume 100.00
Example 9 In order to use these compositions to impart the de sired shade to human hair one part of the selected composition is mixed with approximately 1 to 2 parts of 6% hydrogen peroxide solution.
The resulting solution is then applied to white hair and allowed to remain in contact with the treated hair for about half an hour after which the hair is rinsed and shampooed. After drying the hair assumes the shade as described.
It is understood that the foregoing detailed description is given merely by way of illustration and that many variations may be made therein without departing from the spirit of our invention.
We claim:
1. Process for imparting a greenish-blue coloration to hair which comprises contacting hair with an aqueous solution of about 0.01% to 2% by weight of 2,3,6-triaminopyridine or the salts of 2,3,6-triaminopyridine in the presence of an oxidizing agent.
2. Process for imparting a greenish-blue coloration to hair which comprises. contacting said hair with an aqueous solution containing about 0.01% to 2% by weight of 2,3,6-triaminopyridine or the salts of 2,3,-6-triaminopyridine in the presence of a hydrogen peroxide solution.
3. A composition for dyeing hair which comprises as active ingredient of about 0.01% to 2% by weight of 2,3,6-triaminopyridine or the salts of 2,3,6-triaminopyridine in an aqueous solvent.
4. A composition for dyeing hair which comprises as active ingredient of about 0.01% to 2% by weight of 2,3,6-triaminopyridine or the salts of 2,3,6-triaminopyridine and about 0.01% to 2% by weight of 2,6-diaminopyridine.
5. A composition for dyeing hair which comprises as active ingredients about 0.01 to 2.0% by weight of 2,3,6- triaminopyridine and 0.01% to 2.0% of o-, m-, or p-diaminobenzenes or combinations thereof.
6. A method for dyeing hair which comprises contacting hair with a composition in accordance with claim 5 in the presence of an oxidizing agent.
6 7. A method in accordance with claim 6 wherein said References Cited ggigilizriilieifiglliiteis hydrogen peroxide, urea peroxide or UNITED STATES PATENTS 8. A composition for dyeing hair which comprises as 3,200,040 8/1965 Lange at 167 88 active ingredients of about 0.01 to 2.0% by weight of 5 2,3,6-triaminopyridine and 0.01% to 2.0% of 0-, m-, or ALBERT MEYERS Prlmary Exammer' p-diaminopyridines. VERA C. CLARKE, Assistant Examiner.
Claims (1)
1. PROCESS FOR IMPATING A GREENISH-BLUE COLORATION TO HARI WHICH COMPRISES CONTACTING HAIR WITH AN AQUEOUS SOLUTION OF ABOUT 0.01% TO 2% BY WEIGHT OF 2,3,6-TRIAMINOPYRIDINE OR THE SALTS OF 2,6,6-TRIAMINOPYRIDINE IN THE PRESENCE OF AN OXIDIZING AGENT.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US569851A US3359168A (en) | 1966-08-03 | 1966-08-03 | Dyeing hair with 2, 3, 6-triaminopyridine and salts thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US569851A US3359168A (en) | 1966-08-03 | 1966-08-03 | Dyeing hair with 2, 3, 6-triaminopyridine and salts thereof |
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| Publication Number | Publication Date |
|---|---|
| US3359168A true US3359168A (en) | 1967-12-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US569851A Expired - Lifetime US3359168A (en) | 1966-08-03 | 1966-08-03 | Dyeing hair with 2, 3, 6-triaminopyridine and salts thereof |
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| US (1) | US3359168A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3893802A (en) * | 1970-04-10 | 1975-07-08 | Oreal | Indamines and method of using the same |
| US3898032A (en) * | 1971-06-11 | 1975-08-05 | Zotos Int Inc | Oxidative hair-coloring mixtures containing a conditioning agent |
| US3948596A (en) * | 1973-06-22 | 1976-04-06 | Societe Anonyme Dite: L'oreal | Oxidation dye for keratinic fibers containing 2-halo-5-acetaminophenol as a coupler |
| US3961879A (en) * | 1973-06-22 | 1976-06-08 | L'oreal | Dye composition for keratinic fibers containing a phenol coupler |
| US4003699A (en) * | 1974-11-22 | 1977-01-18 | Henkel & Cie G.M.B.H. | Oxidation hair dyes based upon tetraaminopyrimidine developers |
| US4043750A (en) * | 1975-04-12 | 1977-08-23 | Henkel & Cie Gmbh | Developer-coupler hair dyes based on triamino-pyrimidinones |
| US4046503A (en) * | 1975-04-12 | 1977-09-06 | Henkel & Cie Gmbh | Developer-coupler hair dyes based on alkoxy-triamino-pyrimidines |
| USRE30199E (en) * | 1973-11-29 | 1980-01-29 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Oxidation hair dyes based upon tetraaminopyrimidine developers |
| FR2832148A1 (en) * | 2001-11-14 | 2003-05-16 | Oreal | New 2,5-diaminopyridine derivatives useful as developers in oxidation dye compositions for dyeing keratinic fibers, especially human hair |
| FR2845387A1 (en) * | 2002-10-04 | 2004-04-09 | Oreal | NEW HETEROAROMATIC TRINOCAL BLACK DIRECT COLORANTS |
| US20050060815A1 (en) * | 2002-10-04 | 2005-03-24 | Sylvain Kravtchenko | Novel heteroaromatic trinuclear black direct dyes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3200040A (en) * | 1961-03-22 | 1965-08-10 | Hans Schwarzkopf | Hair dye comprising diaminopyridines |
-
1966
- 1966-08-03 US US569851A patent/US3359168A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3200040A (en) * | 1961-03-22 | 1965-08-10 | Hans Schwarzkopf | Hair dye comprising diaminopyridines |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3893802A (en) * | 1970-04-10 | 1975-07-08 | Oreal | Indamines and method of using the same |
| US3898032A (en) * | 1971-06-11 | 1975-08-05 | Zotos Int Inc | Oxidative hair-coloring mixtures containing a conditioning agent |
| US3948596A (en) * | 1973-06-22 | 1976-04-06 | Societe Anonyme Dite: L'oreal | Oxidation dye for keratinic fibers containing 2-halo-5-acetaminophenol as a coupler |
| US3961879A (en) * | 1973-06-22 | 1976-06-08 | L'oreal | Dye composition for keratinic fibers containing a phenol coupler |
| USRE30199E (en) * | 1973-11-29 | 1980-01-29 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Oxidation hair dyes based upon tetraaminopyrimidine developers |
| US4003699A (en) * | 1974-11-22 | 1977-01-18 | Henkel & Cie G.M.B.H. | Oxidation hair dyes based upon tetraaminopyrimidine developers |
| US4046503A (en) * | 1975-04-12 | 1977-09-06 | Henkel & Cie Gmbh | Developer-coupler hair dyes based on alkoxy-triamino-pyrimidines |
| US4043750A (en) * | 1975-04-12 | 1977-08-23 | Henkel & Cie Gmbh | Developer-coupler hair dyes based on triamino-pyrimidinones |
| FR2832148A1 (en) * | 2001-11-14 | 2003-05-16 | Oreal | New 2,5-diaminopyridine derivatives useful as developers in oxidation dye compositions for dyeing keratinic fibers, especially human hair |
| EP1312606A1 (en) * | 2001-11-14 | 2003-05-21 | L'oreal | 2,5-diaminopyridine oxidation bases and their use for dyeing of keratin fibres |
| US20030163876A1 (en) * | 2001-11-14 | 2003-09-04 | Laurent Vidal | Novel 2,5-diaminopyridine oxidation bases for the dyeing of keratin fibres |
| US6837908B2 (en) | 2001-11-14 | 2005-01-04 | L'oreal S.A. | 2,5-diaminopyridine oxidation bases for the dyeing of keratin fibres |
| FR2845387A1 (en) * | 2002-10-04 | 2004-04-09 | Oreal | NEW HETEROAROMATIC TRINOCAL BLACK DIRECT COLORANTS |
| WO2004031173A1 (en) * | 2002-10-04 | 2004-04-15 | L'oreal | Novel direct black dyes with three heteroaromatic rings |
| US20050060815A1 (en) * | 2002-10-04 | 2005-03-24 | Sylvain Kravtchenko | Novel heteroaromatic trinuclear black direct dyes |
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