US3337411A - Oxidation dyestuffs with ascorbic acid or salts thereof for dyeing living human hair - Google Patents

Oxidation dyestuffs with ascorbic acid or salts thereof for dyeing living human hair Download PDF

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US3337411A
US3337411A US232826A US23282662A US3337411A US 3337411 A US3337411 A US 3337411A US 232826 A US232826 A US 232826A US 23282662 A US23282662 A US 23282662A US 3337411 A US3337411 A US 3337411A
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phenylenediamine
oxidation
hair
ascorbic acid
dyeing
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US232826A
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English (en)
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Wilmsmann Hermann
Konrad Eugen
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Interpal SA
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Interpal SA
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    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to the dyeing of human hair, and more particularly to the use of oxidation hair dyestuffs for the dyeing of human hair whereby improved dyeing eiiects are achieved.
  • the present invention mainly comprises a composition for dyeing human hair, comprising an oxidation hair idyes-tuff which is adapted upon oxidation to ⁇ dye human hair, and a compound selected from the group consisting of ascorbic acid and salts thereof.
  • the composition may contain ran oxidizing ⁇ agent in addition, by being mixed with an oxidizing agent shortly prior to application to the hair, particularly in the case of the use of oxidation dyestutfs which require an oxidation agent in addition to atmospheric oxygen in order to achieve the ⁇ dyeing eiiect in a satisfactory period of time, or the composition, where using an oxidation dyestuft which can be rapidly dyed by means of atmospheric oxygen, maybe free of an extra oxidation agent.
  • superior dyeing eiiects are achieved by the use of ascorbic :acid or .a salt thereof in accordance with the present invention.
  • the activity of the ascorbic acid according to the present invention is 4the same with both ⁇ optical isomers thereof, namely with Vitamin C, the known L-form, 'and also with iso-ascorbic acid, the known D-form. Consequently in all of the discussion in this yapplication whenever the term ascorbic acid is used, this refers -to both optical isomers, or eithe'r one.
  • the present invention is 'applicable to Ithe use of lall inorganic or organic lamine salts of ascorbic acid, particularly those salts the cations ⁇ of which are used to give an alkaline pH to the composition, for example sodium, potassium, ammonium, and organic amine salts such las monoethanolamine, diethanolamine, triethanolamine, isopropanolamine, and the like.
  • the present invention is applicable to the use of all common oxidation hair dyestutfs that can be used for the dyeing of human hair, for example those indicated in the Colour Index, 2nd edition, 1956, volume 3, pages 35934601.
  • oxidation hair dyestuifs for use according to the present invention are:
  • the ascorbic acid and salts thereof which are used as reducing agents according to the present invention in addition to giving the normal reducing agent effect of preventing prem-ature oxidation of the hair dyestuffs, quite surprisingly, as will be explained below also increase the depth of shape resulting from the use of the hair dyesltuff. Thus, with greater amounts of the ascorbic acid or salts thereof ⁇ the depth of shade is increased and darker shades are obtained.
  • the amount of the ascorbic acid or salt thereof for the purposes of ⁇ the :presen-t invention may be as little as 0.5%
  • oxidation dyestuff and the ascorbic acid and the maximum amount of the ascorbic acid or salt thereof is to an extent mainly limited by the expense. In general amounts of greater than by Weight are not necessary and in order to prevent undue expense should not be used. The ⁇ most preferred amount of ascorbic acid or salt thereof is about 0.5-3% by weight.
  • the oxidation dyestuff may be used in any amount ordinarily used for the dyeing of hair, the amount depending of course upon the dyestuif and upon the depth of shade desired. In general amounts of about 0.1-8% by weight are used.
  • oxidation dyestuff compositions in which the oxidation occurs solely by the atmospheric oxygen Iand to oxidation dyestuff compositions which utilize an oxidizing agent such as hydrogen peroxide, urea peroxide or sodium, potassium or ammonium perborates, percarbonates or perphospha-tes, such as sodium perborate, potassium perborate, sodium pe-rcarbonate, potassium percarbonate, ammonium perphosphate, sodium per-phosphate, etc.
  • an oxidizing agent such as hydrogen peroxide, urea peroxide or sodium, potassium or ammonium perborates, percarbonates or perphospha-tes, such as sodium perborate, potassium perborate, sodium pe-rcarbonate, potassium percarbonate, ammonium perphosphate, sodium per-phosphate, etc.
  • the ascorbic acid and salts thereof is at rleast equal in effect to the commonly used reducing agents such as thioglycolic acid or sultes, while with respect to the obtaining of a deep coloring effect and coloring development, the ascorbic acid and salts thereof of the present invention gives far superior results.
  • the lightness of color with addition of ascorbic acid or its salts in the produced dyestuff composition is comparable with the lightness of color obtained by the use of thioglycolic acid additives to the dyestuff compositions, both of these additions giving a markedly lighter color than with the addition of sulfate to the composition.
  • FIGS. 1-3 of the drawings The principal distinct behavior characteristics of ascorbic acid in the presence of hydrogen peroxide in hair dyestutf compositions based on the use of p-toluylenediamine as dyestuff is shown in FIGS. 1-3 of the drawings.
  • the curves give the increase in darkness of the dyestutf after the addition of hydrogen peroxide, measured in percentual absorption with a photoelectric colorimeter (Dr. B. Lange, Model V) with an inserted green filter, in a 100 cc. ask, during a time period of 30 minutes.
  • the dyestuff which directly before the measurement is mixed with an equal volume of 6% hydrogen peroxide, contained in different tests normal reduction equivalent amounts of ascorbic acid, thioglycolic acid or sodium sulte.
  • the dyestuff agents had the compositions set forth in the following examples, in which Examples 1-4 correspond to FIGS. 1-4, respectively.
  • Example I p-Toluylenediamine-sulfate (0.01 mol) g 2.2 Sodium hydroxide (0.02 mol) g 0.8 Ethylenediaminetetraacetic acid, disodium salt g-- 0.1 Aqueous ammonia solution, 25% cc-- 5.0 Reducing agent and water, q.s. cc-- 100 Reducing agent:
  • Example 4 The decisive difference in the speed of oxidation is Y shown in FIG. 4.
  • Aqueous reduction equivalent ⁇ amounts of ascorbic acid, thioglycolic acid and sodium sulfite are shaken in an oxygen atmosphere of accurately determined volume and the amount of oxygen used up in relationship to the time is measured.
  • the solutions have the following compositions:
  • the ascorbic acid is already oxidized after a few minutes, while the oxidation of thioglycolic acid and sodium sulte is not completely even after hours.
  • suitable ascorbic acid concentration it i's possible to adjust at will the time within 30 minutes that the ascorbic acid is completely used up.
  • the ascorbic acid concentration is preferably so chosen that the coloring mass is in contact with the hair for 5 to 10 minutes before the ascorbic acid is used up. ⁇
  • Example 5 Light blond human hair is wetted with the dyeing agent, permitted to said for 30 minutes in the air, and then rinsed and dried.
  • the dyeing agents have the following compositions:
  • Dyeing agent according Color of the dycstui Color oi the dyed to Example composition hair Weak yellowish- Medium blond. Deep blue violet Light blond. Weak yellowish. Dark blond. 5d.. do Llght-light blond. 5e Dark brown Do.
  • Example 6 Gray human hair is wetted with 50 cc. of a dyeing agent which shortly before use is mixed with 50 cc. of 6% hydrogen peroxide, after 30 minutes of working time is rinsed, and then dried.
  • the dyeing agent has the following composition: Oleic acid g 35.0 Isopropyl alcohol cc 15.0 25% aqueous ammonia solution cc 18.0 Ascorbic acid g-- 0.3 p-Toluylenediamine-sulfate g 0.8 2,4diaminoanisol-sulfate ..-g 0.06 m-Aminophenol g-- 0.1 Resorcinol g 0.2 p-Aminophenol g 0.3
  • the dyeing agent has a weakly yellow color and it dyes the hair to a dark ash blond tone with good covering.
  • Example 7 20 g. of cetyl alcohol, 2 g. of sodium cetyl sulfate and g. of wool wax are heated to melting and emulsiied with 30 g. of water at 70 C. Into the still hot emulsion is introduced a hot solution of 1.1 g of p-toluylenediamine-sulfate, 0.1 g. of 2,4diaminoanisolsu1fate, 0.04 g. of m-aminophenol, 0.3 g. of resorcinol, 0.1 g. of sodium sulite, 0.5 g. of ascorbic acid as well as cc. of 25% aqueous ammonia solution in 33 cc. of water, and the mixture is stirred until cooled.
  • Example 8 5.0 g. of sodium lauryl sulfate, 8.0 cc. of 25% aqueous ammonia solution, 0.2 g. of disodium salt of ethylenediamine tetraacetic acid and 1.0 g. of ascorbic acid are dissolved in 60 cc. of water, and then mixed with a solution of 2.0 g. of 2,4-diaminophenol-dihydrochloride in cc. of water and diluted with water to a volume of 100 cc. This slightly yellowish solution is used to wet gray human hair, and the hair after 30 minutes of action thereon is rinsed and dried. The hair is thus thoroughly dyed to a hazelnut blond color.
  • a composition for dyeing human hair comprising an oxidation hair dyestu adapted upon oxidation to dye human hair; an oxidizing agent; and a compound selected from the group consisting of ascorbic acid and salts thereof.
  • a composition for dyeing human hair comprising an alkaline carrier adapted for application to human hair; an oxidation hair dye'stuff adapted upon oxidation to dye human hair and being in an amount of about 0.1- 8% by Weight; and a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof in an amount of about 0.05 to 10% by weight.
  • a composition for dyeing human hair comprising an alkaline carrier adapted for application to human hair; an oxidation hair dyestuff adapted upon oxidation to dye human hair and being in an amount of about 0.1-8% by weight; a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof in an amount of about 0.05 to 10% by weight; and an oxidizing agent in an amount suicient to oxidize said compound and said dye to thereby activate said dye and cause dyeing of human hair to which the composition is applied.
  • a composition for dyeing human hair comprising an alkaline lcarrier adapted for application to human hair; an oxidation hair dyestui adapted upon oxidation to dye human hair and being in an amount of about 0.1-8% by weight; a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof in an amount of about 0.05 to 10% by weight; and an oxidizing agent selected from the group consisting of hydrogen peroxide, urea peroxide and sodium, potassium and ammonium perborates, percarbonates and perphosphates in an amount suicient to oxidize said compound and said dye to thereby activate said dye and Icause dyeing of human hair to which the composition is applied.
  • a composition for dyeing human air comprising an oxidation hair dyestuff adapted upon oxidation to dye human hair and being selected from the group consisting of o-phenylenediamine, p-phenylenediamine, 4-nitro-ophenylenediamine, 4-nitroo-phenylenediamine-dihydrochloride, m-phenylenediamine, 4-chloro-m-phenylenediamine, 4-nitro-mphenylenediamine, toluene-2,4-diamine, salts of toluene-2,4-diamine, toluene-2,5-diamine, 5-nitrotoluene-2,4-diamine, toluene-2,5diaminesulfate, 2-chlorotoluene-3,5diamine, 4-methoxy-m-phenylenediamine, 4 methoxy m phenylenediamine sulfate, 5 methoxyp-phenyl
  • a composition for dyeing human hair comprising an alkaline carrier adapted for application to human hair; an oxidation hair dyestuff adapted upon oxidation to dye human hair and being selected from the group consisting of o-phenylenediamine, p-phenylenediamine, 4nitroo phenylenediamine, 4-ntro-o-phenylenediamine-dihydro chloride, m-phenylenediamine, 4-chloro-m-phenylenedamine, 4-nitroam-phenylenediamine, toluene-2,4-diamine, salts of toluene-2,4-diamine, toluene-2,5-diamine, 5-nitrotoluene-2,4-diamine, toluene-2,5-diamine-sulfate, 2chlo rotoluene3,5diamine, 4-methoxy-m-phenylenediamine, 4 methoxy m phenyl
  • a composition for dyeing human hair comprising an alkaline carrier adapted for application to human hair; an oxidation hair dyestuff adapted upon oxidation to dye human hair and being selected from the group consisting of o-phenylenediamine, p-phenylenediamine, 4-nitro-ophenylenediamine, 4-nitro-o-phenylenediamine-dihydro chloride, m-phenylenediamine, 4-chloro-m-phenylenediamine, 4-nitro-m-phenylenediamine, toluene-2,4-diamine, salts of toluene-2,4-diamine, toluene-2,5-diamine, 5- nitrotoluene-2,4diamine, toluene-2,5diamine-sulfate, 2-
  • a composition for dyeing human hair comprising an alkaline carrier adapted for application to human hair; an oxidation ha-ir dyestutf adapted upon voxidation to dye human hair and being present in -an amount of about 0.1-8% by weight, said oxidation hair dyestuif being selected from the group consisting of o-phenylenediamine, p phenylenediamine, 4 nitro o phenylenediamine, 4- nitro o phenylenediamine dihydrochloride, m phenylenedi-amine, 4 chloro m phenylenediami-ne, 4 nitrom phenylenediamine, toluene 2,4 diamine, salts of toluene 2,4 diamine, toluene 2, diamine, 5 nitrotoluene 2,4 diamine, toluene 2,5 diamine sulfate, 2- chlorotoluene 3,5 diamine, 4 methoxy m pheny
  • the method of dyeing human hair which comprises applying to human hair to be dyed in an alkaline medium a compound selected from the gnoup consisting of ascorbic acid and inorganic salts and organic amine salts thereof, and an oxidation hai-r dyestuif adapted upon oxidation by atmospheric oxygen to dye the hair.
  • the method of dyeing human hair which comprises applying to human hair to be dyed in an ⁇ alkaline medium a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof, an oxidation hair dyestuff adapted to be oxidized by an oxidizing agen-t and upon oxidation to dye the hair, and an oxidizing agent for said oxidation hai-r dyestuif.
  • the method of dyeing human hair which comprises applying to human hair to be dyed an alkaline carrier containing about 0.05 to 10% by Weight of a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof, and also containing an oxidation hair dyestuff adapted upon oxidation by atmospheric oxygen to dye the hair.
  • an alkaline carrier containing about 0.05% to 10% by weight of a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof, and also containing about 0.1-8% by Weight of an oxidation hair dyestuff adapted upon oxidation by atmospheric oxygen to dye the hair.
  • the method of dyeing human hair which comprises applying to human hair to be dyed an alkaline carrier containing about 0.05% to 10% by weight of a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof, and also containing an oxidation hair dyestuif adapted to be oxidized by an oxidizing agent and upon oxidation to dye the hair, and oxidizing agent for said oxidation hair dyestuff.
  • the method of :dyeing human hair which comprises lapplying to human hair to be dyed an alkaline carrier containing about 0.05% to 10% by Weight of a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof, and also containing an oxidation hair dyestuff adapted to be oxidized by an oxidizing agent and upon oxidation to dye the hair, and an oxidizing agent fo-r said Oxidation hair dyestuff selected from the group consisting of hydrogen peroxide, urea peroxide and sodium, potassium and ammonium perborates, percarbonates and perphosphates.
  • the method of dyeing human hair which comprises applying to huma-n hair to be dyed in an ⁇ alkaline medium a compound selected from the group consist-ing of ascorbic acid and inorganic salts and organic amine salts thereof, and an oxidation hair dyestuif adapted upon oxidation by atmospheric oxygen to dye the hair and being selected from the group consist-ing of o-phenylenediamine, pphenylenediamine, 4-nitro o phenylenediamine, 4-nitroo phenylenediamine dihydrochloride, m phenylenediamine, 4 chloro rn phenylenediamine, 4 nitro mphenylenediamine, toluene 2,4 diamine, salts of toluene- 2,4 diamine, toluene 2,5 diamine, 5 nitro toluene- 2,4 diamine, toluene 2,5 diamine sulfate, 2 chlorotoluene 3,5 diamine, 4 meth
  • the method of dyeing human hair which comprises applying to human hair to be dyed an alkaline carrier containing about 0.05% to 10% by Weight of a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof, and also containing an oxidation hair dyestuff adapted to be oxidized by an oxidizing agent and upon oxidation to dye the hair and being selected from the group consisting of o-phenylenediamine, p-phenylenediamine, 4- nitro-o-phenylenediamine, 4 nitro-o-phenylenediaminedihydrochloride, m phenylenediamine, 4 chloro mphenylenediamine, 4 nitro-m-phenylenediamine, toluene- 2,4-diamine, salts of toluene-2,4-diamine, toluene-2,5- Y
  • a composition for dyeing human hair comprising p-phenylenediamine and a compound selected from the g-roup consisting of ascorbic acid and inorganic salts and organic amine salts thereof.
  • a composition for dyeing human hair comprising p-toluenediamine and a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof.
  • a composition for dyeing human hair comprising 5-methoxy-p-phenylenediamine and a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof.
  • the method of dyeing human hair which comprises ap-plying to human hair to be dyed in an alkaline medium an eiective amount of a compound selected from the group consisting of ascorbic acid and inorganic salts and organic amine salts thereof, and an effective amount of an oxidation hair dyestuff selected from the group consisting of p-phenylenediamine, p-toluenediamine and 5- methoxy-p-phenylenediamine.
  • a composition for dyeing human hair comprising in an alkaline medium ⁇ an oxidation hair dyestuff adapted upon oxidation to dye human hair; and the sodium salt of ascorbic acid.
  • composition for dyeing human hair compris ⁇ ing in an alkaline medium an oxidation hair dyestui adapted upon oxidation to dye human hair; and the potassium salt of ascorbic acid.
  • a composition for dyeing human hair comprising in an alkaline medium an oxidation hair dyestui adapted upon oxidation to dye human hair; and the ammonium salt of ascorbic acid.
  • a composition for dyeing human hair comprising in an alkaline medium an oxidation hair dyestui adaptedupon oxidation to dye human hair; and an organic amine salt of ascorbic acid.
  • a method for dyeing living human hair comprising applying to the human air an oxidation hair dyestut and a compound selected from the group consisting of ascorbic acid and salts thereof.
  • composition for dyeing human hair comprising an oxidation hair dyestuff; and a compound selected from the group consisting of ascorbic acid and salts thereof.
  • composition as defined in claim 26, wherein said salt is selected from the group consisting of inorganic salts and organic amine salts of ascorbic acid.
  • composition as dened in claim 28, wherein said salt is selected from the group consisting of inorganic salts and organic amine salts of ascorbic acid.

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US232826A 1961-10-26 1962-10-24 Oxidation dyestuffs with ascorbic acid or salts thereof for dyeing living human hair Expired - Lifetime US3337411A (en)

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DEW30946A DE1149497B (de) 1961-10-26 1961-10-26 Mittel zum Faerben menschlicher Haare

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US (1) US3337411A (en, 2012)
CH (1) CH454357A (en, 2012)
DE (1) DE1149497B (en, 2012)
GB (1) GB979266A (en, 2012)
NL (1) NL284202A (en, 2012)

Cited By (20)

* Cited by examiner, † Cited by third party
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US3899288A (en) * 1971-12-02 1975-08-12 Jean Galerne Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid
US3910289A (en) * 1972-03-21 1975-10-07 Wella Ag Permanent wave composition for hair and process of using it
US3920384A (en) * 1974-07-17 1975-11-18 Clairol Inc Autoxidizable hair dye containing preparations
US3931912A (en) * 1971-08-12 1976-01-13 The Gillette Company Two-part hair dye or hair bleach package
US3948596A (en) * 1973-06-22 1976-04-06 Societe Anonyme Dite: L'oreal Oxidation dye for keratinic fibers containing 2-halo-5-acetaminophenol as a coupler
US3960476A (en) * 1970-03-03 1976-06-01 Giuliana Ghilardi Lyophilized and spray dried dyes
US3961879A (en) * 1973-06-22 1976-06-08 L'oreal Dye composition for keratinic fibers containing a phenol coupler
US3981677A (en) * 1974-01-02 1976-09-21 Clairol Incorporated Oxidative hair dye compositions containing N-substituted o-phenylenediamines and method for their use
US4010872A (en) * 1968-08-28 1977-03-08 Dart Industries Inc. Oxidation hair dye in a plural-fluids dispensing package
US4054413A (en) * 1974-07-17 1977-10-18 Clairol Incorporated Autoxidizable hair dye containing preparations
US4065255A (en) * 1975-06-26 1977-12-27 L'oreal 2-Methyl-5-N-hydroxyalkylaminophenol in an oxidation dye composition and method of using the same
US4169703A (en) * 1978-08-03 1979-10-02 Syntex (U.S.A.) Inc. Oxidative red hair dye
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
US4321053A (en) * 1979-02-17 1982-03-23 Wella Aktiengesellschaft Hair dyeing composition and process
US5782933A (en) * 1997-04-30 1998-07-21 Bristol-Myers Squibb Company Ascorbic and isoascorbic acids to remove or adjust oxidative color in hair
WO1998052522A1 (en) * 1997-05-23 1998-11-26 The Procter & Gamble Company Hair colouring compositions and their use
US6364913B1 (en) * 1996-05-13 2002-04-02 Henkel Kommanditgesellschaft Auf Aktien Agent and process for dyeing and tinting keratinous fibres
WO2004045567A1 (en) * 2002-11-19 2004-06-03 Dsm Ip Assets B.V. Use of ascorbic acid derivatives in hair care products
EP1707188A1 (en) * 2005-04-02 2006-10-04 Wella Aktiengesellschaft Reductive colouring system for keratin fibres
EP1707187A1 (en) * 2005-04-02 2006-10-04 Wella Aktiengesellschaft Reductive colorant for keratin fibres

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FR2421606A1 (fr) * 1978-04-06 1979-11-02 Oreal Procede de teinture de fibres keratiniques en deux temps
FR2955493B1 (fr) * 2010-01-28 2012-02-24 Oreal Utilisation de derives d'acide ascorbique en coloration des fibres keratiniques humaines, composition les comprenant, procede de coloration et dispositif

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US2375250A (en) * 1943-03-19 1945-05-08 Claude R Wickard Antioxidant compositions
US2376884A (en) * 1941-08-07 1945-05-29 Schering Corp Hydroquinone composition
US2934396A (en) * 1957-02-02 1960-04-26 Oreal Process of dyeing hair with 5, 6-dihydroxyindole

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DE541404C (de) * 1927-06-14 1932-01-11 Frau Ida Fehrmann Haarfaerbemittel
BE478770A (en, 2012) * 1946-12-14
FR1052622A (fr) * 1952-03-20 1954-01-26 & Tech Modernes Lab Procédé pour la teinture des poils et cheveux et préparation pour la mise en oeuvre de ce procédé
FR1137922A (fr) * 1955-11-25 1957-06-05 Oreal Procédé et composition pour teindre les cheveux vivants et fibres analogues

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US2376884A (en) * 1941-08-07 1945-05-29 Schering Corp Hydroquinone composition
US2375250A (en) * 1943-03-19 1945-05-08 Claude R Wickard Antioxidant compositions
US2934396A (en) * 1957-02-02 1960-04-26 Oreal Process of dyeing hair with 5, 6-dihydroxyindole

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4010872A (en) * 1968-08-28 1977-03-08 Dart Industries Inc. Oxidation hair dye in a plural-fluids dispensing package
US3960476A (en) * 1970-03-03 1976-06-01 Giuliana Ghilardi Lyophilized and spray dried dyes
US3931912A (en) * 1971-08-12 1976-01-13 The Gillette Company Two-part hair dye or hair bleach package
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WO2006107595A1 (en) * 2005-04-02 2006-10-12 The Procter & Gamble Company Reductive colorant for keratin fibres
WO2006107594A1 (en) * 2005-04-02 2006-10-12 The Procter & Gamble Company Reductive colouring system for keratin fibres
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CH454357A (de) 1968-04-15
GB979266A (en) 1965-01-01
NL284202A (en, 2012) 1900-01-01
DE1149497B (de) 1963-05-30

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