US3251744A - Naphthazarin hair dyeing composition and method - Google Patents

Naphthazarin hair dyeing composition and method Download PDF

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Publication number
US3251744A
US3251744A US257117A US25711763A US3251744A US 3251744 A US3251744 A US 3251744A US 257117 A US257117 A US 257117A US 25711763 A US25711763 A US 25711763A US 3251744 A US3251744 A US 3251744A
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US
United States
Prior art keywords
hair
dyeing
naphthazarin
composition
water
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
Application number
US257117A
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English (en)
Inventor
Walter H Brunner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
P&G Hair Care Holding Inc
Original Assignee
Clairol Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Clairol Inc filed Critical Clairol Inc
Priority to US257117A priority Critical patent/US3251744A/en
Priority to GB44122/63A priority patent/GB1003600A/en
Priority to DEC31426A priority patent/DE1229251B/de
Priority to FR955451A priority patent/FR1379157A/fr
Priority to SE1363463A priority patent/SE198642C1/xx
Priority to CH1506563A priority patent/CH458630A/de
Application granted granted Critical
Publication of US3251744A publication Critical patent/US3251744A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A61K8/355—Quinones
    • 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
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • Disperse dyes which are non-ionic, generally have very low aflinity for hair. Those few which are used for direct dyeing of the hair, for example nitrophenylenediamine derivatives, give weak dyes which wash out readily.
  • naphthoquinones have little value as dyes for hair.
  • 1,2-naphthoquinone and 1,4-naphthoquinone have only poor affinity for normal gray hair under various conditions of dyeing.
  • Henna whose principal color component is 2-hydroxy-1,4-naphthoquinone, has long been used for dyeing hair. However, it is effective only when applied from acid medium, and then gives an unstable reddish tint which darkens progressively on wearing, giving an unpredictable shade.
  • Juglone which S-hydroxy-l,4 nap?hthoquinone, gives only transient shades on hair, and is now rarely used.
  • naphthazarin has good aflim'ty for human hair at temperatures which are below 40 C. when applied in suitable. compositions. It is not necessary to apply naphthazarin as a thick viscous paste,
  • Naphthazarin does not stain or irritate the scalp nor damage the hair. It gives a strong purple shade of a permanent nature, which does not change on wearing, and is fast to rubbing and shampooing. The shade is substantially uniform on various kinds of human hair such as natural gray, permanent waved, and bleached hair. It is produced by direct dyeing without the use of developing agents such as peroxides.
  • compositions of this invention can contain the conventional adjuvan ts of hair dyeing compositions in addition to the naphthazarin such as Water soluble surface active agents, thickening agents and alkalizing agents.
  • naphthazarin such as Water soluble surface active agents, thickening agents and alkalizing agents.
  • Tinctorially effective quantities of naphthazarin in the compositions can vary over a wide range such as that of 3,251,744 Patented May 17, 1 966 1 about 0.01% to greater than about 5%, e.g. by weight of the composition and preferably from about 0.01% to about 2% by weight.
  • the water content of the composition is ordinarily the major constituent and can vary over a wide range dependent in large measure on the quantity of other additives.
  • the water content can be as little as 10% and preferably from about 70% to 99%
  • the water soluble surface active agents employed in the compositions can be anionic, non-ionic or cationic.
  • lauryl sulfate polyoxyethylene laurylester
  • myristyl sulfate glyceryl monostearate
  • sodium salt of palmitic methyl taurine cetyl pyridinium chloride
  • lauryl sulfonate myristyl sulfonate
  • lauric diethanola-mide a surfactant there can be mentioned: lauryl sulfate; polyoxyethylene laurylester; myristyl sulfate; glyceryl monostearate; sodium salt of palmitic methyl taurine; cetyl pyridinium chloride; lauryl sulfonate; myristyl sulfonate; lauric diethanola-mide;
  • the quantity of water soluble surface active agent can vary over a wide range such as that of from about 0.25% to 15% and preferably from about 0.25% to 10% by weight of the composition.
  • the thickening agent may be one or several. of those commonly used in hair dyeing, such as sodium alginate or gum arabic, or cellulose derivatives such as methylcellulose, or the sodium salt of carboxymethylcellulose, or acrylic polymers, such as polyacrylic acid sodium salt, or inorganic thickeners such as bentonite.
  • the quantity of thickening agent can vary over a wide range such as that of from about 0.1% to 20% and preferably from about 0.5% to 5% by weight of the composition.
  • the pH of the composition can vary from about 2.5 to about 11, but it is preferred that the compositions be in the alkaline range and particularly at a pH of about 7.5 to 10. Any selected water dispersible compatible alkalizing agent, if it is desired to have the compositions in the alkaline range, can be used to give the desired pH.
  • The, quantity of the alkalizing agent employed can vary over a wide range depending on the particular alkalizing agent employed and the desired pH. Illustratively, the alkalizing agent can vary from less than about 0.1% to about 10% and preferably from about 0.25% to about 5% by weight of the composition.
  • Any water-soluble alkalizing agent that will not interfere (i.e., is compatible) with the dye employed, and will' amine such as morpholine, N-ethylmorpholine, piperidine,
  • N-ethylpiperidine, 2-pipecoline, or piperazine N-ethylpiperidine, 2-pipecoline, or piperazine.
  • the alkalizing component is preferably a water-soluble organic amine of 10v; volatility (B.P. higher'than about 50 C.) having less than about 12 carbon atoms, such as n-propylamine, isobutylamine, 2-ethylbutylamine, dieth Particularly suited as the alylamine, triethylamine.
  • V kalizing agent are the following: (a) aliphatic diamines 3 or polyamines, such as ethylenediamine, 1,2-diarninopropane, 1,3-diaminopropane, diethylenetriamine,' triethylenetetramine, dipropylenetriamine and N(2-aminocthyl) morpholine; (b) alkanolamines, such as ethanolamine, isopropanolamine, diethanolamine, and triethanolamine, which may also have a phenyl substituent, e.g. an aryldialkanolamine, such as N-phenyldiethanolamine.
  • alkanolamines such as ethanolamine, isopropanolamine, diethanolamine, and triethanolamine, which may also have a phenyl substituent, e.g. an aryldialkanolamine, such as N-phenyldiethanolamine.
  • the acid employed for adjusting the pH can be any inorganic or organic acid or acid salt which is compatible with the composition and will not introduce toxicity under its conditions of use.
  • acids or acid salts there can be mentioned: sulfuric, formic, acetic, lactic,
  • citric or tartaric acid or ammonium sulfate, sodium dihydrogen phosphate, or potassium bisulfate.
  • the dyeing compositions of this invention can be prepared by the conventional methods used in the hair dyeing art. Thus, they can be prepared by dissolving or dispersing the dye in water of the desired concentration. Water miscible organic solvents can be employed to facilitate solution of the dye; in this event, the dye can be dissolved first in the solvent and then diluted with water. The dispersion of the various ingredients can also be facilitated by heating the composition.
  • the dyeing compositions can be applied to living human hair on the head by the conventional techniques known in the art. Illustratively they can be poured over the hair or applied with a brush, sponge, or other means of contact until the hair is properly impregnated.
  • the time of contact of the dyeing composition with the hair is not critical and can varyover the wide range used in the hair dyeing art, such as periods of about 5 minutes to 2 hours or more, and preferably from about to 60 minutes.
  • the dyeing on live hair- is preferably effected at temperatures below 40 C. such as those from C. to 40 C. and preferably at ambient room temperatures such as those of about C. to 35 C.
  • the dispersion was homogeneous it was further diluted, to 100 ml., and the pH was adjusted to 9.5 by the addition of citric acid.
  • the dye composition so obtained was poured on natural gray hair, on permanent wa'ved hair, and on bleached hair, and allowed to remain on the hair for 20 minutes at 38 C. Finally, the hair was rinsed in clear water and dried. All the types of hair were dyed to an approximately equal strength of purple/color, which was fast to rubbing and shampooing.
  • the dyeing compositions of this invention can be aqueous dispersions in the usual generic sense as embracing true solutions of the dye and the other ingredients in water. or in any aqueous medium within the bounds of s the invention as well as intimate admixtures of the dye.
  • aqueous dispersions in the usual generic sense as embracing true solutions of the dye and the other ingredients in water. or in any aqueous medium within the bounds of s the invention as well as intimate admixtures of the dye.
  • Example I A mixture consisting of the following ingredients was heated at 50 C. for ten minutes with occasional stirring to effect a homogeneous dispersion:
  • the above dispersion was then further dilutedwith water to a volume of 100 ml., and citric acid was added to give a pH of 9.9.
  • the dye composition so obtained was poured on natural gray hair, permanent waved hair and bleached hair, and allowed to impregnate the hair for 20 minutes at 30 C. Afterwards the hair was rinsed in clear water and dried in air. All hair was dyed a strong purple coloration.
  • Example 2 A mixture of the following materials was heated at 50 C. for ten minutes with stirring until they were effectively dispersed:
  • the aqueous medium also includes the aqueous alkaline or acid medium or for example, a sufiicient amount of a compound, e.g. ethanol, employed as a common solvent to enhance the solution of the dye or some other organic material.
  • a compound e.g. ethanol
  • the dyeing compositions of this invention can be formulated as pastes, gels, or flowable liquids.
  • aqueous dispersion contains an organic amine alkalizing agent selected fiom the class of aliphatic diamines and polyamines, alkanolamines, and aryldialkanolamines.
  • a hair dyeing composition consisting essentially of an aqueous dispersion containing: (a) a tinctorially effective amount of naphthazarin; (b). a water-soluble sur face active agent; (c) a thickening agent and (d) an organic amine alkalizingagent having less than about 12 carbon atoms, said composition having a pH between about 7.5 and 11.
  • a hair dyeing composition consisting essentially of an aqueous dispersion containing: (a) from about 0.01% to about 10% of naphthazarin; (b) from about 0.25% to about'l5% of a Water-soluble surface active agent; (0) from about 0.1% to about 20% of a thickening agent; and (d) a suflicient quantity of an organic amine alkalizing agent having less than about 12 carbon atoms to impart a pH of about 7.5 to 11 to the aqueous disperson.
  • a hair dyeing composition consisting essentially of an aqueous dispersion containing: (a) from about 0.01% to about 5% of naphthazarin; (b) from about 0.25% to about 10% of awater-soluble surface active agent; (c) from about 0.5% to about 10% of a thickening agent;.and (d) a suflicient quantity of an organic "amine alkalizing agent having less than about 12 carbon atoms to impart a pH of about 7.5 to about 10 to the dispersion. 4
  • a hair dyeing composition consisting essentially of an aqueous dispersion containing: (a) from about 0.01%

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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)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
US257117A 1963-02-08 1963-02-08 Naphthazarin hair dyeing composition and method Expired - Lifetime US3251744A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US257117A US3251744A (en) 1963-02-08 1963-02-08 Naphthazarin hair dyeing composition and method
GB44122/63A GB1003600A (en) 1963-02-08 1963-11-08 Hair dyeing compositions
DEC31426A DE1229251B (de) 1963-02-08 1963-11-14 Naphthazarin-Haarfaerbemittel
FR955451A FR1379157A (fr) 1963-02-08 1963-11-29 Composition de teinture pour cheveux à base de naphtazarine
SE1363463A SE198642C1 (de) 1963-02-08 1963-12-09
CH1506563A CH458630A (de) 1963-02-08 1963-12-09 Haarfärbemittel

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US257117A US3251744A (en) 1963-02-08 1963-02-08 Naphthazarin hair dyeing composition and method

Publications (1)

Publication Number Publication Date
US3251744A true US3251744A (en) 1966-05-17

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US257117A Expired - Lifetime US3251744A (en) 1963-02-08 1963-02-08 Naphthazarin hair dyeing composition and method

Country Status (5)

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US (1) US3251744A (de)
CH (1) CH458630A (de)
DE (1) DE1229251B (de)
GB (1) GB1003600A (de)
SE (1) SE198642C1 (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3415607A (en) * 1965-03-01 1968-12-10 Warner Lambert Pharmaceutical Hair dye composition containing 2-hydroxy-1,4-naphthoquinone
US4605419A (en) * 1984-04-20 1986-08-12 Shiseido Company Ltd. 5,8-dihydroxy naphthalene-1,4-dione derivative and a hair dye composition containing the same
US5416145A (en) * 1992-03-02 1995-05-16 E. I. Du Pont De Nemours And Company Aqueous anionic dye based ink jet inks

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2159056A (en) * 1984-04-04 1985-11-27 Alan Alaexander Torrance Sime Biocidal compositions comprising polyhydroxynaphthoquinones

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB712451A (en) * 1951-02-28 1954-07-21 Unilever Ltd Improvements in hair dyeing compositions
US2745788A (en) * 1954-04-30 1956-05-15 Gillette Co Dyeing with quinones or hydroquinones and borohydrides and compositions therefor
GB889813A (en) * 1959-03-12 1962-02-21 Gillette Industries Ltd Improvements in or relating to the dyeing of keratinous fibres
US3041244A (en) * 1957-09-17 1962-06-26 Jerome A Feit Quinone hair dye compositions
US3147288A (en) * 1959-03-12 1964-09-01 Gillette Co Dyeing composition and method

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB712451A (en) * 1951-02-28 1954-07-21 Unilever Ltd Improvements in hair dyeing compositions
US2745788A (en) * 1954-04-30 1956-05-15 Gillette Co Dyeing with quinones or hydroquinones and borohydrides and compositions therefor
US3041244A (en) * 1957-09-17 1962-06-26 Jerome A Feit Quinone hair dye compositions
GB889813A (en) * 1959-03-12 1962-02-21 Gillette Industries Ltd Improvements in or relating to the dyeing of keratinous fibres
US3147288A (en) * 1959-03-12 1964-09-01 Gillette Co Dyeing composition and method

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3415607A (en) * 1965-03-01 1968-12-10 Warner Lambert Pharmaceutical Hair dye composition containing 2-hydroxy-1,4-naphthoquinone
US4605419A (en) * 1984-04-20 1986-08-12 Shiseido Company Ltd. 5,8-dihydroxy naphthalene-1,4-dione derivative and a hair dye composition containing the same
US5416145A (en) * 1992-03-02 1995-05-16 E. I. Du Pont De Nemours And Company Aqueous anionic dye based ink jet inks

Also Published As

Publication number Publication date
SE198642C1 (de) 1965-09-28
CH458630A (de) 1968-06-30
DE1229251B (de) 1966-11-24
GB1003600A (en) 1965-09-08

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