US3231471A - 2, 6-dioxypyridine and acid addition salts thereof for dyeing human hair - Google Patents
2, 6-dioxypyridine and acid addition salts thereof for dyeing human hair Download PDFInfo
- Publication number
- US3231471A US3231471A US234863A US23486362A US3231471A US 3231471 A US3231471 A US 3231471A US 234863 A US234863 A US 234863A US 23486362 A US23486362 A US 23486362A US 3231471 A US3231471 A US 3231471A
- Authority
- US
- United States
- Prior art keywords
- hair
- dioxypyridine
- dyeing
- color
- grams
- 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
- 238000004043 dyeing Methods 0.000 title claims description 30
- 150000003839 salts Chemical class 0.000 title description 22
- 239000002253 acid Substances 0.000 title description 10
- 238000000034 method Methods 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 244000172533 Viola sororia Species 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 230000037308 hair color Effects 0.000 description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 235000005811 Viola adunca Nutrition 0.000 description 4
- 240000009038 Viola odorata Species 0.000 description 4
- 235000013487 Viola odorata Nutrition 0.000 description 4
- 235000002254 Viola papilionacea Nutrition 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 235000019646 color tone Nutrition 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 239000006103 coloring component Substances 0.000 description 3
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 3
- 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 2
- KZTWOUOZKZQDMN-UHFFFAOYSA-N 2,5-diaminotoluene sulfate Chemical compound OS(O)(=O)=O.CC1=CC(N)=CC=C1N KZTWOUOZKZQDMN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000118 hair dye Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- RYZCLUQMCYZBJQ-UHFFFAOYSA-H lead(2+);dicarbonate;dihydroxide Chemical compound [OH-].[OH-].[Pb+2].[Pb+2].[Pb+2].[O-]C([O-])=O.[O-]C([O-])=O RYZCLUQMCYZBJQ-UHFFFAOYSA-H 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 2
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-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
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- HVHNMNGARPCGGD-UHFFFAOYSA-N 2-nitro-p-phenylenediamine Chemical compound NC1=CC=C(N)C([N+]([O-])=O)=C1 HVHNMNGARPCGGD-UHFFFAOYSA-N 0.000 description 1
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 1
- OOZQLPDAELLDNY-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 OOZQLPDAELLDNY-UHFFFAOYSA-N 0.000 description 1
- AQSOTOUQTVJNMY-UHFFFAOYSA-N 7-(dimethylamino)-4-hydroxy-3-oxophenoxazin-10-ium-1-carboxylic acid;chloride Chemical compound [Cl-].OC(=O)C1=CC(=O)C(O)=C2OC3=CC(N(C)C)=CC=C3[NH+]=C21 AQSOTOUQTVJNMY-UHFFFAOYSA-N 0.000 description 1
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
- 101100436011 Dictyostelium discoideum arcE gene Proteins 0.000 description 1
- 101100217136 Dictyostelium discoideum arpH gene Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- LHRXTFDXJQAGAV-UHFFFAOYSA-L disodium 3-hydroxy-4-(naphthalen-1-yldiazenyl)naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Oc1c(cc2cc(ccc2c1N=Nc1cccc2ccccc12)S([O-])(=O)=O)S([O-])(=O)=O LHRXTFDXJQAGAV-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- -1 p-toluylenediamine Chemical compound 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000011282 treatment Methods 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
- A61K8/49—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
- the present invention relates to a hair dyeing method and composition. More particularly, the present invention is concerned with imparting a violet color or tinge to hair, for instance in order to shade other color tones such as a frequently undesirable yellow.
- the demands which must be met by the coloring components of present day hair dyeing preparations are very extensive. It is desired to obtain intensive color tones and the dyed hair should be color fast even after washing and when exposed to sunlight. Furthermore, the color of the hair should not be affected by acidic after-treatments or exposure to sweat.
- the coloring components must not be toxic and must not be capable of causing allergies. Furthermore, it is desirable that the coloring components will give to the hair the desired color even without requirin application of oxidizing agents so that mixing of the dyeing composition with such oxidizng agents or application of the latter to the hair will not be required, thus simplifying the dyeing of the hair and avoiding damage of the same which may be caused by the oxidizing agent.
- violet is an important color since it is the complementary color to the frequently undesirable yellow. Faded and previously blond, yellow-tinged hair can be dyed with violet to a clear silver-white. Furthermore, violet is used as a modifier or nuancing color in combination with other hair dyes. Fashionable hair colors which are predominantly violet or Bordeaux-red require dyes capable of producing an intensive color so that these color tones will be visible even when applied to dark hair.
- Dye compositions which were up to now proposed for the above purpose appear to have certain disadvantages such as instability of the hair color when exposed to acid, low solubility, insufficient color fastness or toxicity.
- the present invention proposes in a method of dyeing hair, the step of applying to hair which is to be dyed a substance selected from the group consisting of 2,6-dioxypyridine and salts thereof.
- the same comprises the steps of applying to hair which is to be dyed an aromatic amine adapted to be oxidized into a dye and selected from the group consisting of pphenylenediamine, p-toluylenediamine, p-aminophenol, p-amino-N-dimethylaniline, 4-amino-diphenylamine, 4,4- diaminodiphenylamine, 4-amino-4-oxydiphenylamine, mtoluylenediamine, m-phenylenediamine, o-nitro-p-phen- 3,231,471 Patented Jan.
- the present invention also contemplates a composition of matter suitable for use in the oxidative dyeing of hair which comprises at least one dye intermediate adapted to be oxidized to form a dye, and at least one substance selected from the group consisting of 2,6-dioxypyridine and salts thereof.
- a fast blue and violet color which is intensive and acid resistant, can be imparted to human hair by treating hair with a slightly acidic, neutral or slightly alkaline solution, cream or paste which contains 2,6-dioxypyridine or salts thereof.
- These compounds are colorless per se but will be developed by exposure to the oxygen of the air or by means of a conventional developer such as hydrogen peroxide so as to give to the hair the desired violet color.
- slightly acidic is meant to denote a pH of between 2.0 and 6.0, the term neutral a pH of between 6.1 and 8.0, and the term slightly alkaline a pH of between 8.1 and 11.0.
- Salts of 2,6-dioxypyridine which may be used in place of 2,6-dioxypyridine include 2,6-dioxypyridine hydrochloride, 2,6-dioxypyridine sulfate and 2,6-dioxypyridine phosphate.
- 2,6-dioxypyridine hydrochloride 2,6-dioxypyridine sulfate
- 2,6-dioxypyridine phosphate 2,6-dioxypyridine hydrochloride
- 2,6-dioxypyridine sulfate 2,6-dioxypyridine phosphate.
- other salts also may be used.
- the dyeing is carried out in an alkaline or slightly alkaline medium it does not matter which salt of 2,6-dioxypyridine is used, as long as, due to the alkaline medium, the free base 2,6-dioxypyridine is formed from such salt.
- Dyeing may be carried out with 2,6-dioxypridine or a salt thereof as the only color forming component, or in combination with other dyes or dye intermediates so as to either give to the hair a bluish or violet color, or to use the violet color component as a complementary color to offset the effect of undesirable yellow color tones, or also to modify and produce nuances of any other hair color;
- the coloring of human hair which is achieved according to the present invention is highly stable even in an acidic medium. Furthermore, uniform and fast dyeing will be achieved even on hair which comprises portions which are of different qualities.
- hair dyes which may be used in combination with 2,6-dioxypridine or salts thereof are those belonging to the groups of aromatic amines, aromatic diamines, aminophenols, diaminopenols, diamino-nitrobenz'ens, diphenylamines and diaminopyridines.
- Example I 0.3 gram 2,6-dioxypyridine is dissolved in 99.7 grams of warm water. The thus formed solution has a pH of 2.5.
- Example II 10.0 grams of an amphoteric shanipooing agent of the type lauryl-ethyl-cycloimidinium-1-hydroxy-3-ethylsodium alcoholate-Z-rnethyl-sodium carboxylate and 2.5 grams of 2,6-dioxypridine hydrochloride are dissolved in 87.5 grams of water.
- the thus formed solution is adjusted with potassium hydroxide to a pH of 9.0 and heated to 60 C. until the solution becomes clear.
- the solution is worked into the wet hair so as to produce a dense foam. After allowing contact with the hair for between and minutes at body temperature, the hair is rinsed and dried.
- Example 111 An emulsion is formed of 25.0 grams molten cetyl alcohol, 2.0 grams molten cholesterol and 2.0 grams sodium cetylsulfate in 40.0 grams of water of 75 C.
- Example IV 1.2 grams of 2,6dioxypyridine hydrochloride, 1.2 grams of p-toluylenediamine sulfate and 0.82 gram of potassium hydroxide are dissolved under heating in 92.78 milliliters of water.
- Dyeing is carried out by mixing 50 milliliters of the last formed solution with 50 milliliters of 6% hydrogen peroxide and applying the thus formed mixture to the hair.
- Example V 1.2 grams of 2,6-dioxypyridine hydrochloride, 1.2 grams p-amino-N-dimethylaniline and 0.6 gram potassium hydroxide are dissolved under heating in 94 milliliters of water. 3.0 milliliters of 25 aqueous ammonia are added. The thus completed solution has a pH of 10.6.
- Example VII 1.2 grams of 2,6-dioxypyridine hydrochloride, 1.2 grams of 4,4-diamino-diphenylamine sulfate and 0.8 gram or" potassium hydroxide are dissolved under heating in 93.8 milliliters of water.
- Example VIII A solution is formed in the manner. described in the preceding examples of 2.0 grams 2,6-dioxypyridine sulfate, 0.8 gram p-toluylenediamine sulfate, 0.8 gram potassium hydroxide and 91.4 grams water. Subsequently 5.0 grams 25% aqueous ammonia are added. The pH of the fin ished solution is 10.8.
- a composition of matter suitable for use in dyeing hair comprising an alkaline carrier material adapted for application to human hair having distributed therethrough a compound selected from the group consisting of 2,6 dioxypyridine, 2,6-dioxypyridine hydrochloride, 2,6-dioxypyridine sulfate and 2,6-dioxypyr1dine phosphate in an amount equal to between about 0.3% and 2.5% of the weight of said composition.
- composition of matter suitable for use in dyeing hair comprising an alkaline carrier material having arpH of between about 8.1 and 11, adapted for application to human hair having distributed therethrough an acid addition salt of 2,6-dioxypyridine in an amount equal to'between about 0.3% and 2.5% of the weight of said composition.
- a composition of matter suitable for use in dyeing hair comprising an alkaline carrier material adapted for application to human hair having distributed therethrough an acid addition salt of 2,6-dioxypyr1dine in an amount equal to between about 0.3% and 2.5 of the weight of said composition.
- a method of dyeing hair comprising the step of applying to hair which is to be dyed a compound selected from the group consisting of 2,6-dioxypyridine, 2,6-dioxyhydrochloride, 2,6-dioxypyridine sulfate and 2,6-dioxypyridine phosphate.
- a method of dyeing hair comprising the step of applying to hair to be dyed in an alkaline medium having a pH of between about 8.1 and 11 and adapted for application to human hair an acid addition salt of 2,6- dioxypyridine.
- a method of dyeing hair comprising the steps of applying to hair to be dyed a carrier substance having distributed thereto an effective amount of a compound selected from the group consisting of 2,6-dioxypyridine, 2,6-dioxypyridine hydrochloride, 2,6-dioxypyridine sulfate and 2,6-dioxypyridine phosphate; allowing said compound to remain in contact with the hair for a time suflicient to cause dyeing of the hair; rinsing the thus dyed hair; and drying said hair.
- a method of dyeing hair comprising the steps of applying to hair to be dyed a carrier material having a pH of between about 8.1 and 11, and adapted for application to human hair having distributed thereto an effective amount of an acid addition salt of 2,6-dioxypyridine; allowing said salt to remain in contact with the hair for a time sufiicient to cause dyeing of the hair; rinsing the thus dyed hair; and drying said hair.
- a method of dyeing hair comprising the steps of applying to hair to be dyed a carrier substance adapted for application to human hair having distributed thereto an effective amount of an acid addition salt of 2,6-dioxypyridine; allowing said salt to remain in contact with the hair for a time sufficient to cause dyeing of the hair; rinsing the thus dyed hair; and drying said hair.
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH30536A DE1141748B (de) | 1961-11-09 | 1961-11-09 | Mittel zum Faerben von menschlichen Haaren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3231471A true US3231471A (en) | 1966-01-25 |
Family
ID=7431782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US234863A Expired - Lifetime US3231471A (en) | 1961-11-09 | 1962-11-01 | 2, 6-dioxypyridine and acid addition salts thereof for dyeing human hair |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3231471A (enrdf_load_stackoverflow) |
| BE (1) | BE624560A (enrdf_load_stackoverflow) |
| DE (1) | DE1141748B (enrdf_load_stackoverflow) |
| GB (1) | GB988914A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3378456A (en) * | 1965-04-05 | 1968-04-16 | Gen Electric | Jet pumping means for a nuclear reactor |
| US4008272A (en) * | 1968-09-09 | 1977-02-15 | Societe Anonyme Dite: L'oreal | N-Thioureido and N-ureido phenylene diamines and method of preparing same |
| US4165967A (en) * | 1976-09-02 | 1979-08-28 | Henkel Kommanditgesellschaft Auf Aktien | Process for dyeing human hair with diazo salts and coupling components |
| US4473375A (en) * | 1981-08-20 | 1984-09-25 | Wella Aktiengesellschaft | Composition and method for the coloring of hair |
| US5560750A (en) * | 1990-05-08 | 1996-10-01 | Preemptive Advertising, Inc. | Compositions and methods for altering the color of hair |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4381920A (en) * | 1979-08-03 | 1983-05-03 | Michael-David Laboratories | Method and composition for dyeing human hair |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2162458A (en) * | 1936-05-08 | 1939-06-13 | Winthrop Chem Co Inc | Hair dye |
-
0
- BE BE624560D patent/BE624560A/xx unknown
-
1961
- 1961-11-09 DE DESCH30536A patent/DE1141748B/de active Pending
-
1962
- 1962-10-15 GB GB38923/62A patent/GB988914A/en not_active Expired
- 1962-11-01 US US234863A patent/US3231471A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2162458A (en) * | 1936-05-08 | 1939-06-13 | Winthrop Chem Co Inc | Hair dye |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3378456A (en) * | 1965-04-05 | 1968-04-16 | Gen Electric | Jet pumping means for a nuclear reactor |
| US4008272A (en) * | 1968-09-09 | 1977-02-15 | Societe Anonyme Dite: L'oreal | N-Thioureido and N-ureido phenylene diamines and method of preparing same |
| US4165967A (en) * | 1976-09-02 | 1979-08-28 | Henkel Kommanditgesellschaft Auf Aktien | Process for dyeing human hair with diazo salts and coupling components |
| US4473375A (en) * | 1981-08-20 | 1984-09-25 | Wella Aktiengesellschaft | Composition and method for the coloring of hair |
| US5560750A (en) * | 1990-05-08 | 1996-10-01 | Preemptive Advertising, Inc. | Compositions and methods for altering the color of hair |
Also Published As
| Publication number | Publication date |
|---|---|
| BE624560A (enrdf_load_stackoverflow) | |
| DE1141748B (de) | 1962-12-27 |
| GB988914A (en) | 1965-04-14 |
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