US3909190A - Hair dyeing process and composition containing {60 -cyano-methanesulfonamido-nitrobenzene derivatives - Google Patents

Hair dyeing process and composition containing {60 -cyano-methanesulfonamido-nitrobenzene derivatives Download PDF

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Publication number
US3909190A
US3909190A US388728A US38872873A US3909190A US 3909190 A US3909190 A US 3909190A US 388728 A US388728 A US 388728A US 38872873 A US38872873 A US 38872873A US 3909190 A US3909190 A US 3909190A
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cyano
methanesulfonamido
nitro
alpha
amino
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US388728A
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English (en)
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Ferdi Saygin
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B51/00—Nitro or nitroso dyes

Definitions

  • An object of the present invention is the develop ment of an a-cyano-methanesulfonamido-nitrobenzene compound having the formula NH,-SO CH CN wherein Y is a member selected from the group consisting of hydrogen, chloro, bromo, and alkoxy having 1 to 4 carbon atoms, and Z is a member selected from the group consisting of amino and hydroxyl.
  • Another object of the invention is the development of an aqueous preparation for the direct dyeing of human hair consisting essentially of 1) from 0.1% to 5% by weight of the above a-cyano-methanesulfonamido-nitrobenzene compounds; (2) from 0% to 30% by weight of a surfactant; (3) from 0% to 25% by weight of a thickener; and (4) from 40% to 99.9% by weight of water.
  • a further object of the invention is the development of an aqueous preparation for the dyeing of human hair consisting essentially of 1) from 0.2% to 5% by weight of an oxidation dyestuff combination. of a developer component, and a coupling component in substantially equimolar amounts, said coupling component consisting essentially of the above wcyano-methanesulfonamido-nitrobenzene compounds; (2) from 0% to 30% by weight of a surfactant; (3) from O to 25% by weight of a thickener; and (4) from 40% to 99.8% by weight of water.
  • a yet further object of the invention is the development of a process for dyeing human hair consisting essentially of applyingto said hair at temperatures ranging from about 150 to 40C for a time sufficient to effect dyeing, an effective amount of either of the above aqueous preparations.
  • the present invention provides novel oz-cyanomethanesulfonamido-nitrobenzene compounds having the formula Examples of compounds of the described type are:.-
  • the compounds in accordance with the invention may be produced by reacting the corresponding nitroamino-phenols or diamino-nitro-benzenes, substituted if required, wiith the stoichiometric quantity of chlorosulfonyl acetonitrile required for the monosubstitution of an amino group.
  • reaction is effected in the presence of a solvent such as aliphatic hydrocarbons, benzene, chlorobenzene, tetrahydrofuran, in such a manner that the chlorosulfonyl acetonitrile dissolved in the particular solvent is added to the nitroamino-phenols or diamino-nitrobenzenes drop by drop while cooling with ice.
  • a solvent such as aliphatic hydrocarbons, benzene, chlorobenzene, tetrahydrofuran
  • the compounds in accordance with the invention are valuable hair dyes. They may be used as direct dyes which produce yellows of various tints. Compared with the starting substances used for their production, which are known as direct dyestuffs, they are characterized by better absorption and fastness properties, and also provide widely differing tints.
  • the compounds in accordance with the invention can be used as yellow couplers in oxidation dyes in combination with conventional developer substances, and the color tints obtainablecan be varied by means of the developer components, and the intensity of the oxidation can be varied through various tints of yellow to brown.
  • a further object of the invention is the use of compounds of the general formula in which Y represents hydrogen, chlorine, bromine, or an alkoxy group having 1 to 4 carbon atoms, and Z represents an NH or OH-group in preparations for dyeing hair.
  • the invention provides an aqueous preparation for the direct dyeing of human hair consisting essentially of (1) from 0.1% to 5% by weight of the above a-cyano-methanesulfonamidonitrobenzene compounds; (2) from to 30%, preferably 0.5% to 30%, by weight of a surfactant; (3) from 0% to 25%, preferably 0.1% to 25%, by weight of a thickener; and (4) from 40% to 99.9%, preferably 40% to 99.3%, by weight of water; as well as an aqueous preparation for the dyeing of human hair consisting essentially of l from 0.2% to 5% by weight of an oxidation dyestuff combination of a developer component and a coupling component in substantially equimolar amounts, said coupling component consisting essentially of the above a-cyano-methanesulfonamidonitrobenzene compounds; (2) from 0% to 30%, preferably 0.5% to 30%, by weight of a surfactant; (3) from O to 25%, preferably 0.
  • Either of the above preparations can be used in the process for dyeing human hair consisting essentially of applying to said hair at temperatures ranging from about 15 to 40C for a time sufficient to effect dyeing, an effective amount of either of the above aqueous preparations.
  • a particular embodiment of this subject of the invention relates to the use of compounds of the abovementioned formulas in combination with conventional developer substances in preparation for the oxidative dyeing of hair.
  • suitable developer substances are the compounds which are normally used for this purpose.
  • the most important examples are primary aromatic amines having a further functional group in the paraposition, or else a 4-aminopyraz0lone.
  • Preferred 4-aminopyrazolones are compounds of the generic formula wherein R and R are hydrogen or an organic radical having 1 to 10 carbon atoms.
  • the organic radical R can be an alkyl having 1 to 10 carbon atoms, an aryl, such as phenyl, hydroxyphenyl, sulfonylphenyl, sulfonamidophenyl, aminophenyl, lower alkylolphenyl, lower alkylphenyl, lower alkylaminophenyl and di-lower alkylaminophenyl where the alkyls and alkylols have 1 to 4 carbon atoms, or a heterrocyclic radical, such as the pyridyl.
  • an aryl such as phenyl, hydroxyphenyl, sulfonylphenyl, sulfonamidophenyl, aminophenyl, lower alkylolphenyl, lower alkylphenyl, lower alkylaminophenyl and di-lower alkylaminophenyl where the alkyls and alkylols have 1 to 4 carbon atom
  • Functional groups may be present, particularly on the aryl, as indicated above, such as OH, NH NHCH N(CH or halogen atoms, i.e., fluorine, iodine, bromine, and particularly chlorine.
  • the following groups may be present as organic radicals: COOH, COOR', CONH CONHR', CONR'R", wherein R and R are alkyl or hydroxyalkyl having 1 to 4 carbon atoms.
  • the organic radical R can be an alkyl having 1 to 10 carbons, an aryl, such as those mentioned above for R or a heterocyclic radical, such as the pyridyl.
  • Functional groups may be present.
  • hydrocarbon radicals having 1 to 10 carbons are applicable containing as functional groups OH, NH COOH, CONH SO H and SO NH
  • aromatic radical a phenyl is especially applicable.
  • alkyl or hydroxyalkyl groups having 1 to 4 carbons or other substituents such as halogen, preferably Cl, NH OH, COOH, CONH- CONHR', CONR'R", SO H and SO NH
  • substituents such as halogen, preferably Cl, NH OH, COOH, CONH- CONHR', CONR'R", SO H and SO NH
  • 4- aminopyrazolone in the form of their water-soluble acid addition salts, such as the hydrochloride, sulfate or oxalate, because the resistance to atmospheric air is increased.
  • diaminoanisole or compounds of the kind named which additionally contain one or more functional groups such as OH, NR NHR', NR'R, where R and R" again are lower alkyls or hydroxyalkyls having 1 to 4 carbon atoms.
  • these aromatic biand polyfunctional amines have the formula wherein Y is a member selected from the group consisting of OH, NH NHR', NR'R and NHC l-l and Z is a member selected from the group consisting of H, R, Y and OR, where again R and R are alkyls or hydroxyalkyls having 1 to 4 carbon atoms.
  • Suitable developers include diamino pyridine and its derivatives, for example 2,5-diamino-pyridine, and heterocyclic hydrazone derivatives, for example pyridone hydrazones such as l-ethyl-pyridone-Z- hydrazone.
  • the coupling components according to the invention are suitably used in substantially equimolar quantities with respect to the developers used. However, it is also possible to employ the coupling component in a certain excess over the stoichiometric amount or in a certain lesser quantity than the stoichiometric amount. Both the coupling components and the developers may be mixtures of compounds of the above-mentioned kind.
  • the oxidative coupling that is, the development of the dyeing, may also be effected according to known procedures such as by the oxygen of the air.
  • chemical oxidizing agents are suitably used, especially hydrogen peroxide orits adducts with urea, melamine and sodium borate, as well as mixtures of such hydrogen peroxide adducts with potassium peroxydisulfate.
  • the compounds according to the invention may be present in the form of aqueous preparations, such as solutions or emulsions.
  • aqueous preparations such as solutions or emulsions.
  • Such preparations should contain the direct'dye or the dyestuffs combination of coupling component and developer component in amounts of from 0.1% to by weight, preferably 0.1% to 2% by weight.
  • the compounds according to the invention may be applied in the form of creams or emulsions.
  • the direct dyes, or mixtures of oxidative dyestuffs combinations of developers and couplers may be mixed with the ingredients usually present in such preparations.
  • Such ingredients include any anionic or nonionic wetting agents or detergents such as for example, alkylbenzenesulfonates, fatty alcohol sulfates, higher alkylsulfonates, higher fatty acid ethanolamides, or ethylene oxide adducts on higher fatty acids, higher fatty alcohols or alkylphenols.
  • such preparations may contain thickeners, as for example, methylcellu: lose, starch and also higher fatty alcohols, paraffin oil and fatty acids, as well as perfume oils or hair treatment agents, for example pantothenic acid and cholesterol,
  • the additives are utilized in the amounts effective for this purpose.
  • An effective amount of a wetting agent or surfactant added is especially from 0.5% to 30% by weight; and an effective amount of a thickening agent added is from 0.1% to 25% by weight, calculated in each case on the total composition.
  • the concentration of the direct dye or the dyestuffs combinations in such cream or emulsion preparations is from 0.1% to. 5% by weight preferably 0.2% to 2%, based upon the .total composition, depending on the purpose for which the agent is to be used.
  • the application of the direct dye or dyestuffs combinations may be effected at temperatures between C and 40C preferably room temperature, in weakly acid, neutral or preferably alkaline medium.
  • the dyeings obtained have the advantages of a good light fastness, a good washing fastness and a good fastness to rubbing.
  • a special advantage of the hair dyes according to the invention is that they may be used both in direct dyeing and as coupling components in oxidation dyestuffs to obtain yellow colorations.
  • EXAMPLE 2 4-amino-2-( a-eyano-methanesulfonamido l -nitrobenzene calculated for EXAMPLE 3 1-amino'-4-( a-cyano-methanesulfonamido )-2-nitrobenzene 15.3 gm (0.1 mol) of 1,4-diamino-2-nitro-benzene dissolved in 200 ml of absolute tetrahydrofuran, and 14 gm (0.1 mol) of chlorosulfonyl acetonitrile dissolved in 50 ml of absolute tetrahydrofuran were reacted in the manner described in Example 1. The reaction product was recrystallized from ethanol. The precipitate filtered off was washed with a little ether and was subsequently recrystallized again from water.
  • the precipitate was recrystallized twice from ethanol.
  • EXAMPLE 8 2 parts by weight of 1-amino-2-(oz-cyano-methanesulfonamido)-4-nitro-benzene were incorporated in a cream base of the composition:
  • the emulsion was adjusted to a pH value of 9.5 by adding ammonia and was subsequently made up to 100 parts by weight with water.
  • the dyeing cream thus obtained dyed human hair mustard brown to yellowist brown within 30 minutes by virtue of the action of the atmospheric oxygen or a 1% or 9% solution of hydrogen peroxide.
  • the various tints of color were obtained in accordance with the oxidation. agents used (or their different concentrations).
  • An aqueous preparation for the direct dyeing of 50 a-cyano-methanesulfonamido-nitrobenzene compound human hair consisting essentially of (1) from 0.1% to is selected from the group consisting of l-amino-2-(a- 5% by weight of an a-cyano-methanesulfonamidocyano-methanesulfonamido)-4-nitr0-benzene, 4- nitrobenzene compound having the formula amino-2-(a-cyano-methanesulfonamido)-l-nitro- 55 benzene, l-amino-4-( a-cyano-methanesulfonamido Z 2-nitro-benzene, 4-chloro-2-( a-cyano-methanesulfonamido )-6-nitro-phenol, 6-chloro-2-(a-cyanomethanesulfonamido
  • a process for direct dyeing human hair consisting 2 essentially of applying to said hair at temperatures ranging from about 15C to 40C for a time sufficient to effect dyeing, an effective amount of the aqueous wherein Y is a member selected from the group consistpreparatons of clalm ing of hydrogen, chloro, bromo and alkoxy having 1 to 4 carbon atoms, and Z is a member selected from the 4.
  • An aqueous preparation for the dyeing of human hair consisting essentially of (1) from 0.2% to 5% by weight of an oxidation dyestuff combination of a developer component and a coupling component in substantially equimolar amounts, said coupling component consisting essentially of an a-cyano-methanesulfonamido-nitrobenzene compound having the formula wherein Y is a member selected from the group consisting of hydrogen, chloro, bromo and alkoxy having 1 to 4 carbon atoms, and Z is a member selected from the group consisting of amino and hydroxyl; (2) from to by weight of a surfactant selected from the group consisting of an anionic wetting agent and a nonionic wetting agent; (3) from O to 25% by weight of a thickener; and (4) from to 99.8% by weight of water.
  • a-cyano-methanesulfonamido-nitrobenzene compound is selected from the group consisting of l'-amino-2-( acyano-methanesulfonamido)-4-nitro-benzene, 4 amin- 0-2-( a-cyano-methanesulfonamido 1 -nitro-benzene, l-amino-4-( a-cyano-methanesulfonamido )-2-nitrobenzene, 4-chloro-2-(a-cyano-methanesulfonamido)- 6-nitro-phenol, 6-chloro-2-(a-cyano-methanesulfonamido)-4-nitro-phenol, Z-(a-cyano-methanesulfonamido)-4-nitro-phenol, and 4-(a-cyanomethanesulfonamido)-2-nitro-phenol.
  • aqueous preparation of claim 4 wherein said developer component is selected from the group consisting of a 4-amino-pyrazolone, a water-soluble acid addition salt of said 4-amino-pyrazolone, an aromatic amine having at least one primary amino group and another functional group in the para-position, a diaminopyridine and a pyridone hydrazone.
  • aqueous preparation of claim 4, wherein said developer component is selected from the group consisting of 4-aminol -phenyl-3-carbamoyl-pyrazolone-5 4-amino-1-phenyl-3-ethoxycarbonyl-pyrazolone-5, 4- aminolH-3-ethoxycarbonyl-pyrazolone-5, p-toluylene diamine, 1-methyl-pyridone-2-hydrazone and lmethyl-quinolone-4-hydrazone.
  • a process for dyeing human hair consisting essentially of applying to said hair at temperatures ranging from about 15 to 40C for a time sufficient to effect dyeing, an effective amount of the aqueous preparation of claim 4.

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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)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
US388728A 1972-08-21 1973-08-16 Hair dyeing process and composition containing {60 -cyano-methanesulfonamido-nitrobenzene derivatives Expired - Lifetime US3909190A (en)

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DE2241015A DE2241015A1 (de) 1972-08-21 1972-08-21 Alpha-cyanmethansulfonamidobenzolderivate

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US (1) US3909190A (fr)
AR (1) AR201288A1 (fr)
AT (1) AT323330B (fr)
AU (1) AU5939373A (fr)
BE (1) BE803712A (fr)
BR (1) BR7306355D0 (fr)
DE (1) DE2241015A1 (fr)
FR (1) FR2196997A1 (fr)
GB (1) GB1394146A (fr)
IT (1) IT1048134B (fr)
NL (1) NL7310581A (fr)
ZA (1) ZA735717B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4599450A (en) * 1983-05-13 1986-07-08 Hoechst Aktiengesellschaft Process for the preparation of acid nitro dyestuffs
US4980158A (en) * 1989-04-04 1990-12-25 Clairol Incorporated Nitroaniline dyes with a cyano substituent group
US5024673A (en) * 1989-04-04 1991-06-18 Clairol Incorporated Nitroaniline dyes with a cyano substituent group
US6503282B1 (en) * 2000-01-07 2003-01-07 Wella Aktiengesellschaft Means and method for dying keratinic fibers
US6537329B1 (en) * 1999-01-21 2003-03-25 L'oreal S.A. Cationic 2-sulphonylaminophenols, their use as couplers for oxidation dyeing, compositions containing them and dyeing methods

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2315256A1 (fr) * 1975-06-26 1977-01-21 Oreal Coupleurs nitres utilisables en teintures directes, teintures d'oxydation et teintures mixtes
DE4018335A1 (de) * 1990-06-08 1991-12-12 Wella Ag Mittel zum faerben von haaren mit einem gehalt an 2-amino-4-halogen-6-nitrophenolen sowie 2-amino-4-fluor-6-nitrophenol
FR2816501B1 (fr) * 2000-11-14 2003-03-28 Oreal Utilisation de 2-sulphonylamino-phenols comme coupleurs en coloration d'oxydation

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2441491A (en) * 1944-05-12 1948-05-11 Ilford Ltd Cyanacetylamino phenol color formers for color photography
US3388148A (en) * 1965-06-16 1968-06-11 Warner Lambert Pharmaceutical Nu-cyanoethyl derivatives of nitro-p-phenylenediamine
US3629330A (en) * 1965-05-24 1971-12-21 Clairol Inc Components for hair dyeing compositions
US3649160A (en) * 1968-05-17 1972-03-14 Oreal Dyeing human hair with oxidation bases and an indoline coupler
US3702861A (en) * 1970-08-03 1972-11-14 Monsanto Co Preparation of n-alkyl anilinomethylenemalononitriles
US3781323A (en) * 1970-02-28 1973-12-25 Bayer Ag Cyano-and trifluoromethyl-substituted 6-nitroanilines

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2441491A (en) * 1944-05-12 1948-05-11 Ilford Ltd Cyanacetylamino phenol color formers for color photography
US3629330A (en) * 1965-05-24 1971-12-21 Clairol Inc Components for hair dyeing compositions
US3388148A (en) * 1965-06-16 1968-06-11 Warner Lambert Pharmaceutical Nu-cyanoethyl derivatives of nitro-p-phenylenediamine
US3649160A (en) * 1968-05-17 1972-03-14 Oreal Dyeing human hair with oxidation bases and an indoline coupler
US3781323A (en) * 1970-02-28 1973-12-25 Bayer Ag Cyano-and trifluoromethyl-substituted 6-nitroanilines
US3702861A (en) * 1970-08-03 1972-11-14 Monsanto Co Preparation of n-alkyl anilinomethylenemalononitriles

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4599450A (en) * 1983-05-13 1986-07-08 Hoechst Aktiengesellschaft Process for the preparation of acid nitro dyestuffs
US4980158A (en) * 1989-04-04 1990-12-25 Clairol Incorporated Nitroaniline dyes with a cyano substituent group
US5024673A (en) * 1989-04-04 1991-06-18 Clairol Incorporated Nitroaniline dyes with a cyano substituent group
US6537329B1 (en) * 1999-01-21 2003-03-25 L'oreal S.A. Cationic 2-sulphonylaminophenols, their use as couplers for oxidation dyeing, compositions containing them and dyeing methods
US6503282B1 (en) * 2000-01-07 2003-01-07 Wella Aktiengesellschaft Means and method for dying keratinic fibers

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DE2241015A1 (de) 1974-02-28
BR7306355D0 (pt) 1974-07-18
AU5939373A (en) 1975-02-20
NL7310581A (fr) 1974-02-25
AR201288A1 (es) 1975-02-28
GB1394146A (en) 1975-05-14
AT323330B (de) 1975-07-10
ZA735717B (en) 1974-04-24
IT1048134B (it) 1980-11-20
FR2196997A1 (fr) 1974-03-22
BE803712A (fr) 1974-02-18

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