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 PDF

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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
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hair
dioxypyridine
dyeing
color
grams
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US234863A
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Lange Fritz-Walter
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics 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.

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  • 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)
US234863A 1961-11-09 1962-11-01 2, 6-dioxypyridine and acid addition salts thereof for dyeing human hair Expired - Lifetime US3231471A (en)

Applications Claiming Priority (1)

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DESCH30536A DE1141748B (de) 1961-11-09 1961-11-09 Mittel zum Faerben von menschlichen Haaren

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US3231471A true US3231471A (en) 1966-01-25

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BE (1) BE624560A (xx)
DE (1) DE1141748B (xx)
GB (1) GB988914A (xx)

Cited By (5)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2162458A (en) * 1936-05-08 1939-06-13 Winthrop Chem Co Inc Hair dye

Patent Citations (1)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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Publication number Publication date
BE624560A (xx)
GB988914A (en) 1965-04-14
DE1141748B (de) 1962-12-27

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