US3128232A - Oxidation dyestuff agent for human hair - Google Patents
Oxidation dyestuff agent for human hair Download PDFInfo
- Publication number
- US3128232A US3128232A US16128A US1612860A US3128232A US 3128232 A US3128232 A US 3128232A US 16128 A US16128 A US 16128A US 1612860 A US1612860 A US 1612860A US 3128232 A US3128232 A US 3128232A
- Authority
- US
- United States
- Prior art keywords
- human hair
- oxidation
- composition
- hair
- diaminobenzoic acid
- 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
- 210000004209 hair Anatomy 0.000 title claims description 43
- 230000003647 oxidation Effects 0.000 title claims description 33
- 238000007254 oxidation reaction Methods 0.000 title claims description 33
- 239000000975 dye Substances 0.000 title description 39
- 239000003795 chemical substances by application Substances 0.000 title description 11
- 239000000203 mixture Substances 0.000 claims description 27
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 claims description 20
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- 150000001340 alkali metals Chemical class 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- -1 alkali metal salts Chemical class 0.000 description 13
- 238000004040 coloring Methods 0.000 description 13
- 238000004043 dyeing Methods 0.000 description 8
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 7
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 7
- 239000007800 oxidant agent Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229960001755 resorcinol Drugs 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 125000005342 perphosphate group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 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
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- KZTWOUOZKZQDMN-UHFFFAOYSA-N 2,5-diaminotoluene sulfate Chemical compound OS(O)(=O)=O.CC1=CC(N)=CC=C1N KZTWOUOZKZQDMN-UHFFFAOYSA-N 0.000 description 1
- SWZVJOLLQTWFCW-UHFFFAOYSA-N 2-chlorobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1Cl SWZVJOLLQTWFCW-UHFFFAOYSA-N 0.000 description 1
- BAJQRLZAPXASRD-UHFFFAOYSA-N 4-Nitrobiphenyl Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 BAJQRLZAPXASRD-UHFFFAOYSA-N 0.000 description 1
- 241000660443 Encyclops Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- SLGRKEQJAOYINT-UHFFFAOYSA-N NC=1C=C(C(=O)[O-])C=CC1N.[NH4+] Chemical compound NC=1C=C(C(=O)[O-])C=CC1N.[NH4+] SLGRKEQJAOYINT-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000003648 hair appearance Effects 0.000 description 1
- 230000003806 hair structure Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004753 textile Substances 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
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
-
- 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
Definitions
- the tone of such coloring is dependent on the pH value, particularly when using for a toning dyestulf the above mentioned necessary toning agents for example m-aminophenol,
- alpha-naphthol, 2,4-diaminotoluene, and 2,4-diaminoanisol In alkaline pH range the coloring tone is shifted towards blue-green while in acid pH range towards red. This so called indicator property is particularly noticeable in an unpleasant manner in the case of hair which has been subjected to usual cosmetic treatments, particularly permanent Waving agents (utilizing agents with pH values of 9.5 or 3) and by acid rinses (in the case of the use of alkaline soaps as well as various curling agents).
- the present invention mainly comprises as an oxidation dyestuff composition for human hair an oxidation dyestuif and 3,4 diaminobenzoic acid or a salt thereof.
- an oxidizing agent such as perborates, percarbonates, perphosphates, hydrogen peroxide or urea peroxide to this composition activates the oxidation dyestuff and the 3,4- diaminobenzoic acid to give a dye composition for human hair which has all of the above enumerated advantages which will be further described and proved below.
- the present invention comprises a method of dyeing human hair which comprises applying to the hair to be dyed an oxidation dyestuff, 3,4-diaminobenzoic acid or a salt thereof and an oxidizing agent such as hydrogen peroxide or urea peroxide.
- the 3,4-diaminobenzoic acid may be combined with all normal oxidation dyestuffs, as set forth in Colour Index, 2nd edition, volume 3, pages 3594-3601.
- the blond tones obtained according to the present invention may be used and achieved utilizing the 3,4-diaminobenzoic acid in combination with already known EXAMPLE 1 20 g. of cetylalcohol, 2 g. of sodium cetylalcohol sulfate and 5 g. of wool wax are heated to melting and emulsified with 40 g. of water at 70 C. Into this hot emulsion is added a likewise hot solution of:
- EXAMPLE 2 This is a comparative test showing the superior effect of the use of 3,4-diaminobenzoic acid in accordance with the present invention.
- the solid substances were used in the amounts set forth in grams while the ammonia solution was used in the amount set forth in cubic centimeters.
- EXAMPLE 3 This example also relates to comparative tests.
- Dye composition for human hair comprising an oxidation dyestuff for human hair, and a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof.
- Dye composition for human hair comprising an oxidation dyestuif for human hair, a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof, and an oxidizing agent adapted to oxidize and thereby activate said oxidation dyestuif.
- composition for human hair comprising an oxidation dyestuif for human hair, a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof, and an oxidizing agent adapted to oxidize and thereby activate said oxidation dyestuff and being selected from the group consisting of perborates, percarbonates, perphosphates, hydrogen peroxide and urea peroxide.
- Dye composition for human hair comprising an oxidation dyestuff for human hair selected from the group consisting of aromatic p-diamines and aminopheno'ls, and a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof.
- composition for human hair comprising p-toluylenediamine as an oxidation dyestuff for human hair, and a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof.
- Dye composition for human hair said composition comprising p-toluylenediamine sulfate as an oxidation dyestuff for human hair, and a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof.
- Dye composition for human hair said composition comprising p-amino-pheno-l as an oxidation dyestuff for human hair, and a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof.
- Dye composition for human hair said composition comprising 4-methyl-amino-phenol as an oxidation dyestuff for human hair, and a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof.
- the method of dyeing human hair which comprises applying to such hair :to be dyed an oxidation dyes-tufi for human hair, -a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof, and an oxidizing agent adapted to oxidize and thereby activate said oxidation dyestuff.
- the method of dyeing human hair which comprises applying to such hair to be dyed an oxidation dyestuff for human hair selected from the group consisting of aromatic p-diamines and aminophenols, a substance selected from the group consisting of 3,4diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof, and an oxidizing agent adapted to oxidize and thereby activate said oxidation dyestulf and being selected from the group consisting of perborates, percarbonates, perphosphates, hydrogen peroxide and urea peroxide.
- an oxidation dyestuff for human hair selected from the group consisting of aromatic p-diamines and aminophenols, a substance selected from the group consisting of 3,4diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof, and an oxidizing agent adapted to oxidize and thereby activate said oxidation dyestulf and being selected from the group consisting of perborates, percarbon
- Dye composition for human hair comprising an oxidation dyestufi for human hair, and a substance selected from the group consisting of 3,4-diaminobenzoic acid and alkali metal, ammonium and organic amine salts thereof in an amount of one-third to two times the weight of said oxidation dyestuif.
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)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEW25261A DE1091707B (de) | 1959-03-21 | 1959-03-21 | Mittel zum Faerben von menschlichen Haaren mit Oxydationsfarbstoffen |
| CH217360A CH383556A (de) | 1959-03-21 | 1963-02-17 | Mittel zum Färben von menschlichen Haaren mit Oxydationsfarbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3128232A true US3128232A (en) | 1964-04-07 |
Family
ID=25689711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US16128A Expired - Lifetime US3128232A (en) | 1959-03-21 | 1960-03-21 | Oxidation dyestuff agent for human hair |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3128232A (de) |
| DE (1) | DE1091707B (de) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3617167A (en) * | 1965-08-05 | 1971-11-02 | Therachemie Chem Therapeut | Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair |
| US3931912A (en) * | 1971-08-12 | 1976-01-13 | The Gillette Company | Two-part hair dye or hair bleach package |
| US4129414A (en) * | 1975-03-03 | 1978-12-12 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Oxidation hair colorants containing water-soluble polyhalogen 3-aminophenols as couplers |
| US4172703A (en) * | 1978-08-03 | 1979-10-30 | Syntex (Usa) Inc. | Oxidative brown hair dye |
| US4302199A (en) * | 1980-12-29 | 1981-11-24 | The Procter & Gamble Company | Hair dyeing method |
| US5350424A (en) * | 1992-10-13 | 1994-09-27 | Combe Incorporated | Dyestuff composition for the gradual dyeing of hair by atmospheric oxidation and process using the same |
-
1959
- 1959-03-21 DE DEW25261A patent/DE1091707B/de active Pending
-
1960
- 1960-03-21 US US16128A patent/US3128232A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3617167A (en) * | 1965-08-05 | 1971-11-02 | Therachemie Chem Therapeut | Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair |
| US3931912A (en) * | 1971-08-12 | 1976-01-13 | The Gillette Company | Two-part hair dye or hair bleach package |
| US4129414A (en) * | 1975-03-03 | 1978-12-12 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Oxidation hair colorants containing water-soluble polyhalogen 3-aminophenols as couplers |
| US4172703A (en) * | 1978-08-03 | 1979-10-30 | Syntex (Usa) Inc. | Oxidative brown hair dye |
| US4302199A (en) * | 1980-12-29 | 1981-11-24 | The Procter & Gamble Company | Hair dyeing method |
| US5350424A (en) * | 1992-10-13 | 1994-09-27 | Combe Incorporated | Dyestuff composition for the gradual dyeing of hair by atmospheric oxidation and process using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1091707B (de) | 1960-10-27 |
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