US3561912A - Oxidation dyes comprising aromatic diamines and coupling components - Google Patents

Oxidation dyes comprising aromatic diamines and coupling components Download PDF

Info

Publication number
US3561912A
US3561912A US585779A US3561912DA US3561912A US 3561912 A US3561912 A US 3561912A US 585779 A US585779 A US 585779A US 3561912D A US3561912D A US 3561912DA US 3561912 A US3561912 A US 3561912A
Authority
US
United States
Prior art keywords
group
developer
hair
hydrogen
parts
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
US585779A
Other languages
English (en)
Inventor
Karl-Josef Boosen
Peter Berth
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.)
Therachemie Chemische Therapeutische GmbH
Original Assignee
Therachemie Chemische Therapeutische GmbH
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 Therachemie Chemische Therapeutische GmbH filed Critical Therachemie Chemische Therapeutische GmbH
Application granted granted Critical
Publication of US3561912A publication Critical patent/US3561912A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • A61K8/40—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
    • A61K8/40—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
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid

Definitions

  • a composition for treatment of human hair comprising a substantially 0.1 to 5.0 weight percent aqueous solution of a developer plus a coupling agent in quantities ranging from substantially equimolar to a slight excess of the developer; said developer having the formula wherein R and R individually are selected from the group consisting of hydrogen, lower hydroxyalkyls, beta methyl sulfonamidoethyl, hydroxyethyls, lower alkyls and interconnected lower alkyls; R is selected from the group consisting of hydrogen, lower alkyl and lower alkoxy; R is lower alkyl; and X is selected from the group consisting of COOH, SO H, -PO H and PO H their water soluble salts, their acid amides and esters with aliphatic alcohols having 1-4 carbon atoms; said coupling agent being selected from
  • the invention relates to agents and compositions for the dyeing of hair. More particularly, it relates to such agents based on oxidation dyes and is suited for the dyeing of human hair, especially living human hair.
  • oxidation dyes for the coloring of human hair has long been known.
  • the coloring components used frequently are aromatic diamines, especially p-phenylenediamine, with or without such known coupling components as phenol. These compounds are converted on the hair into dyes by oxidation either by the influence of atmospheric oxygen or particularly with chemical oxidizers such as hydrogen peroxide.
  • Groups containing hydrophilic pi-electrons usable for the purpose at hand are -COOH, SO H, PO H and -PO H under certain conditions in the form of their water-soluble salts or in the form of the corresponding acid amides or esters of lower aliphatic alcohols having 1-4 carbon atoms.
  • the groups containing hydrophilic pi-electrons are used in the form of their water-soluble salts, especially their alkali salts are of advantage, i.e., their sodium and potassium salts, also the ammonium salts and those formed with organic bases, especially mono-, diand triethanolamine.
  • alkyl radicals in the compounds named as Formula 1, which hereinafter will be referred to as developer components, may be linear or branched.
  • Preferred substituted alkyl radicals are hydroxyalkyl or beta-methylsulfonamidoethyl groups.
  • Lower alkyls are those in the present case which contain 1-5 carbon atoms, and preferably l to 3.
  • Preferred compounds are those wherein R and, under certain conditions, also R are alkyl, and R is hydrogen. If, however, R and/or R are hydrogen, the preferred compounds are those wherein R is an alkyl or alkoxy.
  • R and R may be interconnected and form a heterocyclic ring with the neighboring nitrogen atoms.
  • Numerous compounds may act as coupling components for oxidation hair dyes.
  • aromatic amines and diamines also phenols, naphthols, polyphenols and aminophenols.
  • diamines aminophenols and phenols, orthoand meta-compounds are preferred.
  • heterocyclic methylene couplers i.e., compounds which contain in the heterocyclic radical a methyl.- ene group contiguous to the keto group, such as pyrazolones; furthermore so-called open-chain methylene couplers, i.e., compounds which contain a methylene group contiguous to the keto group in the aliphatic chain, e.g., aroyland acylacetic acid derivatives.
  • Suitable compounds of this type are B-methylpyrazolone- 5) 1-phenyl-3-methylpyrazolone- (5) 1,3-dimethylpyrazolone- 5) acetoacetic acid anilide benzoylacetanilide benzoylacetotoluidide nicotinoylacetanilide
  • the coupling components opportunely are employed in essentially molar quantities with respect to the developer components. However, it generally is not harmful to have the latter present in a certain excess.
  • Coloring of the hair can be developed, as with other oxidation dyes, by the action of atmospheric oxygen or of chemical oxidizers, such as hydrogen peroxide or its addition products, especially on urea, melamine or sodium borate.
  • chemical oxidizers such as hydrogen peroxide or its addition products, especially on urea, melamine or sodium borate.
  • Dyeing of the hair is carried out at temperatures of substantially -40 0, preferably at room temperature.
  • the dyes can be applied in the form of aqueous solutions, but it is preferred to use them in the form of creams or emulsions.
  • the developer components can be mixed with any detergent or washing agent, especially those which are anionic or nonionic.
  • Particularly suitable compounds are alkylbenzenesulfonates, alkylsulfonates, fatty acid ethanolamides, ethylene oxide additives on fatty acids and on fatty alcohols.
  • the coloring effect of the dyes named above is good in admixture with such detergents or washing agents.
  • the hair dyes can be manufactured in the form of shampoos, particularly cream shampoos, which frequently is desired in practice.
  • the agents according to the invention furthermore may contain thickeners, e.g., methylcellulose, carboxymethylcellulose, starch, higher fatty alcohols, vaseline, paraffin oil or fatty acids; also perfumes, i.e., essential oils; and hair treating agents, such as pantothenic acid and cholesterol. It is a matter of course that the compatibility of all these additives named With the other components must be considered.
  • thickeners e.g., methylcellulose, carboxymethylcellulose, starch, higher fatty alcohols, vaseline, paraffin oil or fatty acids
  • perfumes i.e., essential oils
  • hair treating agents such as pantothenic acid and cholesterol.
  • the additives are applied in the customary quantities.
  • Detergents are used particularly in amounts of 0.5 to 30 weight percent, and thickeners in amounts of 0.1 to weight percent, all calcuated on the total composition.
  • concentration of the developer and coupling components, taken together, may be up to 5 percent, preferably 0.1 to 2 weight percent of the total composition.
  • the hair dyes according to the invention are employed preferably in an alkaline pH range, especially at a pH ranging from 8 to 9.5. They lead to colors which have good light-, washand rub-resistance (abrasion resistance) and, contrary to the commonly used agents based on oxidation dyes, can readily be removed from the hair by means of reducing agents such as sodium hydroxymethanesulfinate.
  • the developer components can be produced from the corresponding substituted diamines by reaction with halogenalkylcarboxylic acids or by reaction with S0 and aldehydes and further conversion into the corresponding amides or esters.
  • the manufacture of derivatives containing phosphorus is carried out correspondingly by the reaction of substituted amines with hypophosphorous acid or with phosphorous acid and aldehydes or ketones.
  • EXAMPLE 1 A solution was prepared consisting of 2 parts of a developer component having Formula 2 EXAMPLE 2 A deep violet color was obtained when proceeding as in Example 1, but substituting an equal amount of 1-phenyl-3 methylpyrazolone-(5) for the alpha-naphthol.
  • Example 3 The conditions of Example 1 were duplicated except that 2 parts of a developer component having Formula 3 were used and 1 part m-diaminoanisole in lieu of the alpha-naphthol. The solution dyed naturally grey hair to a strong purplish red color. The coloration was fully removed by a treatment with a 3% aqueous solution of sodium hydroxymethanesulfinate (Rongalit C).
  • EXAMPLE 4 The procedure followed was the same as in Example 1, but 2 parts of a developer component of Formula 4 and 1 part alpha-naphthol were used. Grey hair was dyed blueblack. The same color was obtained when the pH value was adjusted to 7 with ethanolamine in lieu of 9.5 with NH CH2OH2 N-NHOHS 03H Om-CH JH;
  • EXAMPLE 5 2 parts of a developer component having Formula 5 EXAMPLE 6
  • a solution of 2 parts of a compound of Formula 6 onn 1 part benzoylacetanilide and 1 part sodium sulfite in parts water was thickened with 5 parts carboxymethylcellulose, adjusted to a pH of 9.5 with ammonia, and made up to parts with water.
  • the paste thus obtained was mixed with 8 parts melamine perhydrate and applied to grey hair for 20 minutes at room temperature. The hair assumed a yellowish orange color.
  • EXAMPLE 8 The procedure was identical with that given in the preceding example except that in lieu of 1 part alpha-naphthol, 1 part of one of the compounds named in the following table individually were used. The colors thus obtained on grey hair also are listed in the table. All colors could readily be removed from the hair by treatment with a reducing agent.
  • the developer component consisted of 2 parts of a compound of Formula 7, the coupler of 1 part resorcinol, the pH was adjusted to 8.5 with ammonia. Otherwise, the procedure as outlined in Example 1 was followed. Grey human hair attained a red-purple color.
  • a hair dyeing cream was manufactured consisting of 10 parts fatty alcohol (C -C 10 parts fatty alcohol sulfate obtained from coconut oil, 05 part sodium sulfite, 1 part alpha-naphthol, 70 parts water and 1 part of a developer component of Formula 8 HsC The mixture was adjusted to a pH of 9.5 with ammonia and made up to 100 parts with water. 4 parts percarbamide were mixed in prior to use. Grey hair, treated with this cream for minutes at room temperature obtained a deep blue color.
  • EXAMPLE 11 The composition of the hair cream prepared was the same as in Example 10, except that 1 part of a developer component of Formula 9 was used and 1 part 2,4-diaminoanisole as coupler. The cream was adjusted to a pH of 9 with ammonia. After addition of 8 parts melamine perhydrate, .grey hair assumed a brownred color after 20 minutes at room temperature.
  • EXAMPLE 12 1 part of a developer component of Formula 10, 1 part of resorcinol, 1 part sodium sulfite and 92 parts water were thickened with 5 parts carboxymethylcellulose and the paste obtained adjusted to a pH of 9.5 with ethanolamine. 4 parts percarbamide were admixed thereto, and
  • N NHCHz-C O O O2H5 (11) 11 0 EXAMPLE 14 A hair dyeing cream was produced from Parts Fatty alcohol sulfate (from coconut oil) l0 Fatty alcohol (C -C 10 Sodium sulfite 0.5 Developer component Formula 12 l Alpha-naphthol 1 Water 70 The pH was adjusted to 9.0 with ethanolamine, and the mixture made up to parts with water. After adding 4 parts percarbamide to the cream, the same was applied to grey hair for 20 minutes at 25, and a deep blue coloration ensued.
  • R and R individually are selected from the group consisting of hydrogen, lower hydroxyalkyl, beta methyl sulfonarnidoethyl and lower alkyl; R is selected from the group consisting of hydrogen, lower alkyl and lower alkoxy; R is lower alkyl; and X is selected from the group consisting of COOH, SO H, PO H and -PO H their water soluble salts, their acid amides and esters with aliphatic alcohols having 1-4 carbon atoms; said coupling agent being selected from the group consisting of oand m-phenylenediamine; oand m-aminophenol; oand m-toluylenediamine; o-anisidine; 2,4-diaminoanisole; 2,4-diaminophenol; pyrogallol; resorcinol; pyrocatechol; alpha-naphthol; aminoresorcinol; 1,5 aminohydroxynaphthalene; and 1,8 di
  • composition as defined in claim 1 wherein said composition also contains 0.5-30 weight percent of a nom'onic or anionic detergent to act simultaneously as a shampoo.
  • composition as defined in claim 4 also containing a thickener in an amount of 0.1-25 weight percent.
  • a process for the oxidative treatment of human hair with a compound having light-, washingand rub-resistance, yet being readily removable from the hair which comprises applying to said hair for approximately 15 to 30 minutes at a temperature ranging from substantially 15 to 40 C.
  • a composition comprising a substantially 0.5 to weight percent aqueous solution of a developer plus a coupling component in quantities relative to each other ranging from substantially equimolar to a slight excess of said developer; followed by rinsing of the hair; said developer being a compound having the formula wherein R and R individually are selected from the group consisting of hydrogen, lower hydroxyalkyl, beta methyl sulfonamidoethyl, and lower alkyl; R is selected from the group consisting of hydrogen, lower alkyl and lower alkoxy; R is lower alkyl; and X is selected from the group consisting of COOH, SO H, PO H and -PO H their water soluble salts, their acid amides and esters with aliphatic alcohols having
  • R and R are hydrogen and R is selected from the group consisting of lower alkyl and lower alkoxy.
  • said developer is orig-0H2 on;

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)
US585779A 1965-10-30 1966-10-11 Oxidation dyes comprising aromatic diamines and coupling components Expired - Lifetime US3561912A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DET0029697 1965-10-30
DET0031964 1966-09-01

Publications (1)

Publication Number Publication Date
US3561912A true US3561912A (en) 1971-02-09

Family

ID=26000115

Family Applications (1)

Application Number Title Priority Date Filing Date
US585779A Expired - Lifetime US3561912A (en) 1965-10-30 1966-10-11 Oxidation dyes comprising aromatic diamines and coupling components

Country Status (10)

Country Link
US (1) US3561912A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AT (1) AT275049B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CH (1) CH504208A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (2) DE1492201C3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DK (1) DK113377B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ES (1) ES332914A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FR (1) FR1505471A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB1161758A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NL (1) NL6613878A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
SE (1) SE325109B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4268264A (en) * 1978-04-06 1981-05-19 L'oreal Composition for hair dyeing which contains a para base and an ortho base
US20040107515A1 (en) * 2001-04-05 2004-06-10 The Procter & Gamble Company Hair colouring compositions and their use
US20040148713A1 (en) * 2001-07-24 2004-08-05 The Procter & Gamble Company Hair colouring compositions and their use
US7347879B2 (en) 2004-02-27 2008-03-25 L'Oreál, S.A. Sulfur-containing secondary para-phenylenediamines dye compositions comprising such para-phenylenediamines, processes, and uses thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2866882B1 (fr) * 2004-02-27 2017-04-14 Oreal Para-phenylenediamines secondaires soufrees, composition tinctoriale comprenant de telles para-phenylenediamines, procede mettant en oeuvre cette composition et utilisation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4268264A (en) * 1978-04-06 1981-05-19 L'oreal Composition for hair dyeing which contains a para base and an ortho base
US20040107515A1 (en) * 2001-04-05 2004-06-10 The Procter & Gamble Company Hair colouring compositions and their use
US20040148713A1 (en) * 2001-07-24 2004-08-05 The Procter & Gamble Company Hair colouring compositions and their use
US7066967B2 (en) * 2001-07-24 2006-06-27 The Procter & Gamble Company Hair coloring compositions and their use
US7347879B2 (en) 2004-02-27 2008-03-25 L'Oreál, S.A. Sulfur-containing secondary para-phenylenediamines dye compositions comprising such para-phenylenediamines, processes, and uses thereof

Also Published As

Publication number Publication date
DE1617875A1 (de) 1971-06-03
SE325109B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1970-06-22
NL6613878A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1967-05-02
AT275049B (de) 1969-10-10
CH504208A (de) 1971-03-15
FR1505471A (fr) 1967-12-15
ES332914A1 (es) 1968-08-01
DE1492201B2 (de) 1974-10-10
DE1492201A1 (de) 1969-11-20
DK113377B (da) 1969-03-17
GB1161758A (en) 1969-08-20
DE1492201C3 (de) 1975-06-05

Similar Documents

Publication Publication Date Title
US5047066A (en) Dye composition for keratinous fibers containing a 2-substituted 4-aminophenol compound as a developer, and a coupling substance
DK148895B (da) Haarfarvningsmiddel til oxidativ farvning
DE3863698D1 (de) Metaphenylendiamine, verfahren zu deren herstellung, zwischenprodukte und verwendung dieser metaphenylendiamine als kuppler fuer die oxidative faerbung von keratinfasern insbesondere von menschlichem haar.
US3630655A (en) Dyeing human hair with oxidation dyes comprising heterocyclic amino compounds
US4395262A (en) Hair dyeing agent
EP0030680A1 (de) Haarfärbemittel
US3561912A (en) Oxidation dyes comprising aromatic diamines and coupling components
GB1572983A (en) Hair dye compositions
US3617167A (en) Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair
US4487607A (en) Oxidation hair dyes containing 5-halo-2,3-pyridine-diols as coupler components
US3909190A (en) Hair dyeing process and composition containing {60 -cyano-methanesulfonamido-nitrobenzene derivatives
EP0002828B1 (de) Haarfärbemittel
US4046503A (en) Developer-coupler hair dyes based on alkoxy-triamino-pyrimidines
JPS5967217A (ja) 染毛剤
EP0004368A2 (de) Haarfärbemittel
EP0039807B1 (de) Haarfärbemittel
PL174829B1 (pl) Oksydacyjny środek do barwienia włókien keratynowych, zwłaszcza ludzkich włosów
FI88806C (fi) Haorfaergningsmedel innehaollande direktverkande nitrodifenylaminderivat
EP0697854B1 (de) Verwendung von hydroxynaphthalinen in färbemitteln
US5246466A (en) Oxidation dyes
EP0024710A2 (de) Haarfärbemittel
DK148131B (da) Haarfarvemiddel paa basis af oxidationsfarvestoffer
JPS60104007A (ja) 染毛剤
US3695823A (en) Dyeing human hair with n-arylsulfon-amides and aromatic amines
CH489246A (de) Haarfärbemittel