US3216899A - Hair dye comprising m-lower-dialkyl aminophenol and p-mononuclear diamines - Google Patents
Hair dye comprising m-lower-dialkyl aminophenol and p-mononuclear diamines Download PDFInfo
- Publication number
- US3216899A US3216899A US365145A US36514564A US3216899A US 3216899 A US3216899 A US 3216899A US 365145 A US365145 A US 365145A US 36514564 A US36514564 A US 36514564A US 3216899 A US3216899 A US 3216899A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- aminophenol
- dialkyl
- hair
- hair dye
- 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
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 title claims description 14
- 239000000118 hair dye Substances 0.000 title description 10
- 150000004985 diamines Chemical class 0.000 title description 2
- 238000004043 dyeing Methods 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 29
- 241000282414 Homo sapiens Species 0.000 claims description 27
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 210000004209 hair Anatomy 0.000 description 24
- 239000003607 modifier Substances 0.000 description 12
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 10
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 10
- 239000002671 adjuvant Substances 0.000 description 8
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 6
- 229940018563 3-aminophenol Drugs 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 102000011782 Keratins Human genes 0.000 description 4
- 108010076876 Keratins Proteins 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- -1 p-tolylene Chemical group 0.000 description 4
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 3
- AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical group N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000000051 modifying effect Effects 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
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- 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
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
- D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes
Definitions
- This invention relates to a dyeing adjuvant and its use. More particularly, this invention is concerned with new compositions suitable for use in the dyeing of keratin fibers, such as human hair.
- 3-alkoxy-4-aminodiphenyl amines are inoperative in the presently used hair dyeing combinations. It has also been recommended to employ dimethyl aniline or 4-amino-dimethyl aniline in order to produce a dull color elfect.
- these modifiers are unsuitable for use in cosmetic preparations because of their unpleasant odor and pronounced toxicity.
- dyeings produced with these modifiers have an unsatisfactory light fastness.
- Another object of the present invention is to provide dyeing adjuvants which when added to amine-containing dyeing compositions will improve the properties of the colors produced therefrom.
- a further object of the present invention is to provide new amine-containing dyeing compositions suitable for use in the oxidative dyeing of keratin fibers including human hair.
- Yet another object of the present invention is to provide dyeing adjuvants which when applied to hair preserve its natural or artifical color.
- a further object of the present invention is to provide novel compositions which make it possible to dye human hair in such manner that the color obtained does not shift towards red under the action of light and/or perspiration.
- the present invention provides the m-dialkyl aminophenols as a new class of dyeing adjuvants. It has been found in accordance with the present invention that m-dialkyl aminophenols, in particular m-dimethyl aminophenol, produce an excellent modifying effect resulting in the formation of dull, green oxidation dyes. This elfect is all the more surprising since m-aminophenol, which is the parent substance of the m-dialkyl aminophenols and which is also used as a modifier, leads to blue-violet oxidation colors.
- the dialkyl amino phenols of the present invention When combined with an aromatic p-diamine, such as p-tolylene diamine, the dialkyl amino phenols of the present invention produce on human hair, depending upon the ratio of the components used, colors of excellent fastness which range from green to a natural-looking dull brown or blonde.
- the dyeings obtained with the aid of m-dialkyl aminophenols according to the present invention are fast to permanent waving (for example, by preparations based on thioglycolate), weather, washing and all influences of wear.
- a further advantage of the dyeing adjuvants of the present invention is that they can be used at the relatively high pH of the common hair dyeing compositions.
- m-dialkyl aminophenols such as m-dimethyl aminophenol
- these compounds when applied to the keratin of the hair form a greenish dyestufi" under the action of oxygen contained in the air. Therefore, the m-dialkyl aminophenols are capable of counteracting the shift towards red normally observed with hair colors.
- the dyeing adjuvants of the present invention have the added advantage of producing a shift towards green with all commonly used oxidation dyes, such as the aromatic p-diamines. Consequently, none of the mixtures commonly employed in the dyeing of hair will result in the formation of an abnormal color when an m-dialkyl aminophenol is present.
- Meta-dimethyl aminophenol and its homologues such as m-diethyl aminophenol, are physiologically harmless compounds. This finding is in agreement with the data obtained by S. Borelli (Hautmaschine 9, No. 1, 19, 21 (1958)), in studying the behavior of m-aminophenol.
- Example 1 8 parts of an aqueous solution containing 1% of toluylene diamine and 0.25% of resorcinol are mixed with 2 parts of a 1% solution of m-dimethyl aminophenol and 0.5 part of 25% aqueous ammonia. Shortly before the dyeing step, 10 parts of a 6% hydrogen peroxide solution are added to the mixture. The dyeing composition thus produced is allowed to act on human hair of medium brown color at a temperature of 32 C. for a period of 20 minutes. After rinsing and drying, the hair is of a dull, natural-looking brown color.
- Example 2 20 grams of cetyl alcohol, 2 grams of cetyl alcohol sulfate-sodium and 5 grams of wool wax are melted together and then emulsified with 40 grams of water at 70 C. To the hot emulsion there is added a hot solution of 0.3 gram of toluylene diamine, 0.08 gram of resorcinol, 0.01 gram of m-aminophenol and 0.1 gram of m-dimethyl aminophenol in 25 ml. of water, Subsequently, 10 ml. of a 25% ammonia solution are added and the mixture is stirred until cold. 50 grams of the cream thus prepared are mixed with 20 ml. of 6% hydrogen peroxide and the mixture is applied to human hair. After a dyeing time of 30 minutes, a dull, natural-looking blonde tone is obtained.
- a dyeing composition for use in the dyeing of human hair on human beings consisting essentially of a mononuclear aromatic p-diamine, an oxidizing agent and m-lower-clialkyl aminophenol.
- a dyeing composition for use in the dyeing of human hair on human beings consisting essentially of p-toluylene diamine, hydrogen peroxide and m-dimethyl aminophenol.
- a dyeing composition for use in the dyeing of human hair on human beings, consisting essentially of p toluylene diamine, an oxidizing agent and m-lower-dialkyl aminophenol.
- a dyeing composition for use in the dyeing of human hair on human beings consisting essentially of p-toluylene diamine, an oxidizing agent and m-dimethyl aminophenol.
- a dyeing composition for use in the dyeing of human hair on human beings consisting essentially of p-toluylene diamine, an oxidizing agent and m-diethyl aminophenol.
- a dyeing composition for use upon oxidation in the dyeing of human hair on human beings consisting essentially of mononuclear aromatic p-diamine and m-lower-dialkyl aminophenol.
- a dyeing composition for use upon oxidation in the dyeing of human hair on human beings consisting essentially of p-toluylene diamine and m-loWer-dialkyl aminophenol.
- a dyeing composition for use upon oxidation in the dyeing of human hair on human beings consisting essentially of p-toluylene diamine and m-dimethyl aminophenol.
- a dyeing composition for use upon oxidation in the dyeing of human hair on human beings consisting essentially of p-toluylene diamine and m-diethyl aminophenol.
- a hair dye composition which comprises the dyeing composition of claim 1 and a hair dye modifier.
- a hair dye composition which comprises the dyeing composition of claim 1 and a hair dye modifier selected from the group consisting of resorcinol, pyrocatechol, orcinol, chlorohydroquinone, alpha naphthol and maminophenol.
- a hair dye composition which comprises the dyeing composition of claim 6 and a hair dye modifier.
- a hair dye composition which comprises the dyeing composition of claim 6 and a hair dye modifier selected from the group consisting of resorcinol, pyrocatechol, orcinol, chlorohydroquinone, alpha naphthol and m-aminophenol.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical 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)
- Textile Engineering (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEW24442A DE1151900B (de) | 1958-11-13 | 1958-11-13 | Mittel zur Faerbung menschlicher Haare |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3216899A true US3216899A (en) | 1965-11-09 |
Family
ID=7597839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US365145A Expired - Lifetime US3216899A (en) | 1958-11-13 | 1964-05-05 | Hair dye comprising m-lower-dialkyl aminophenol and p-mononuclear diamines |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3216899A (en)van) |
| BE (1) | BE582334A (en)van) |
| DE (1) | DE1151900B (en)van) |
| FR (1) | FR1239890A (en)van) |
| GB (1) | GB868325A (en)van) |
| NL (1) | NL242906A (en)van) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3884627A (en) * | 1971-10-04 | 1975-05-20 | Clairol Inc | Oxidative hair dye compositions |
| US3918896A (en) * | 1973-06-22 | 1975-11-11 | Oreal | Dye composition for keratinic fibers containing an oxidation base and a meta-aminophenol coupler |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4297098A (en) * | 1976-08-26 | 1981-10-27 | Alberto-Culver Company | Method for gradual coloring of hair to a light brown shade and preparations for use therein |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE80814C (en)van) * | ||||
| US3041244A (en) * | 1957-09-17 | 1962-06-26 | Jerome A Feit | Quinone hair dye compositions |
-
0
- BE BE582334D patent/BE582334A/xx unknown
- NL NL242906D patent/NL242906A/xx unknown
-
1958
- 1958-11-13 DE DEW24442A patent/DE1151900B/de active Pending
-
1959
- 1959-11-09 FR FR809651A patent/FR1239890A/fr not_active Expired
- 1959-11-09 GB GB37946/59A patent/GB868325A/en not_active Expired
-
1964
- 1964-05-05 US US365145A patent/US3216899A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE80814C (en)van) * | ||||
| US3041244A (en) * | 1957-09-17 | 1962-06-26 | Jerome A Feit | Quinone hair dye compositions |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3884627A (en) * | 1971-10-04 | 1975-05-20 | Clairol Inc | Oxidative hair dye compositions |
| US3918896A (en) * | 1973-06-22 | 1975-11-11 | Oreal | Dye composition for keratinic fibers containing an oxidation base and a meta-aminophenol coupler |
Also Published As
| Publication number | Publication date |
|---|---|
| GB868325A (en) | 1961-05-17 |
| NL242906A (en)van) | |
| DE1151900B (de) | 1963-07-25 |
| BE582334A (en)van) | |
| FR1239890A (fr) | 1960-08-26 |
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