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US3981678A Expired / Lapsed US ⏱️ 0.0 years remaining

Lyophilized dyes and the use thereof to color keratinic fibers

Assignee: L'Oréal SA
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Filing: 1973-06-25
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Granted: 1976-09-21
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Expires: 1993-06-25
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Abstract

Abstract A process for producing a dye in powder form involves reacting an oxidation agent with an oxidation base in an aqueous alkaline medium, preferably an ammoniacal medium, having a pH ranging from 8 to 13, in the presence of an organic solvent for the dye being produced, at a temperature and during a period of time allowing at least a partial oxidation, preferably between 15 DEG -30 DEG C for a period of about 5 minutes to 30 hours and lyophilizing the resulting reaction product. The resulting dye can be used to color keratinic fibers, especially human hair.

Inventors

  • 👤 Giuliana Ghilardi
  • 👤 Pierre Bore
  • 👤 Jean-Francois Grollier

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 15:23
CPC Classifications
D; D06; D06P; D06P1/00; D06P1/32; A; A61; A61K; A61K8/00; A61K8/02; A61K8/18; A61K8/30; A61K8/40; A61K8/41; A61K8/413; A61K8/415; A61K8/72; A61K8/81; A61K8/817; A61K8/8176; A61Q; A61Q5/00; A61Q5/10; C; C09; C09B; C09B67/00; C09B67/0001; C09B67/0003

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 198 words
A process for producing a lyophilized dyestuff for coloring keratinic fibers consisting essentially of reacting hydrogen peroxide with an oxidation base in an aqueous alkaline solution open to ambient atmosphere in the presence of an organic solvent for the resulting dyestuff, said organic solvent being selected from the group consisting of tert-butyl alcohol, dimethylsulfoxide, dioxane and benzyl alcohol and having a pH ranging from 8 to 13 at a temperature between about 15°-30°C for a period of about 5 minutes to 30 hours and lyophilizing said reaction mixture, the molar raito of said hydrogen peroxide to said oxidation base being between about 0.1:1 to 20:1, said oxidation base being selected from the group consisting of paratoluylene diamine, paraphenylene diamine, N,N-dimethylparaphenylene diamine, methyl paraphenylene diamine, chloroparaphenylene diamine, 2-methoxy-5-methyl paraphenylene diamine, 2,6-dimethyl-3-methoxy paraphenylene diamine, tetramethyl paraphenylene diamine, 2-methoxy paraphenylene diamine, para aminophenol, 2,6-dimethyl para aminophenol, 2,4-diamino anisole, 2-methyl para aminophenol, 1-methoxy-2,5-dimethyl paraphenylene diamine, and the hydrochlorides thereof, wherein lyophilizing said reaction mixture comprises freezing said reaction mixture at a temperature of about -200° to -60°C and subliming said frozen mixture at a temperature of about -50°C to -30°C at a pressure of about 0.01 mm Hg to 0.1 mm Hg.
Claim 2
Dependent Claim 198 words
A process for producing a lyophilized dyestuff for coloring keratinic fibers consisting essentially of reacting hydrogen peroxide with an oxidation base in an aqueous alkaline solution open to ambient atmosphere in the presence of an organic solvent for the resulting dyestuff, said organic solvent being selected from the group consisting of tert-butyl alcohol, dimethylsulfoxide, dioxane and benzyl alcohol and having a pH ranging from 8 to 13 at a temperature between about 15°-30°C for a period of about 5 minutes to 30 hours and lyophilizing said reaction mixture, the molar raito of said hydrogen peroxide to said oxidation base being between about 0.1:1 to 20:1, said oxidation base being selected from the group consisting of paratoluylene diamine, paraphenylene diamine, N,N-dimethylparaphenylene diamine, methyl paraphenylene diamine, chloroparaphenylene diamine, 2-methoxy-5-methyl paraphenylene diamine, 2,6-dimethyl-3-methoxy paraphenylene diamine, tetramethyl paraphenylene diamine, 2-methoxy paraphenylene diamine, para aminophenol, 2,6-dimethyl para aminophenol, 2,4-diamino anisole, 2-methyl para aminophenol, 1-methoxy-2,5-dimethyl paraphenylene diamine, and the hydrochlorides thereof, wherein lyophilizing said reaction mixture comprises freezing said reaction mixture at a temperature of about -200° to -60°C and subliming said frozen mixture at a temperature of about -50°C to -30°C at a pressure of about 0.01 mm Hg to 0.1 mm Hg.
Claim 3
Dependent Claim 27 words
The process of claim 1 which also includes desorbing the lyophilized reaction product at a temperature ranging between 15°-60°C at a pressure of about 0.01 mm Hg.
Claim 4
Dependent Claim 15 words
The process of claim 1 wherein said aqueous alkaline solution in an aqueous ammoniacal solution.
Claim 5
Dependent Claim 113 words
The process of claim 1 wherein said oxidizing agent and said oxidation base are reacted in the presence of filler selected from the group consisting of oligopeptide, amino acid, polyvinylpyrrolidone having a molecular weight ranging between 40,000 to 360,000, a copolymer of vinylpyrrolidone and vinyl acetate having a molecular weight ranging between 40,000 to 160,000 wherein the weight ratio of vinylpyrrolidone to vinyl acetate is 70%:30% to 30%:70% and a copolymer of crotonic acid and vinyl acetate having a molecular weight of 40,000 to 200,000 wherein the weight ratio of crotonic acid to vinyl acetate is 90%:10%, said filler being present in amounts of 1-20 percent by weight of the total reaction mixture.
Claim 6
Dependent Claim 24 words
The process of claim 4 wherein said filler is an amino acid selected from the group consisting of alanine, glycine, glutamic acid and cystine.
Claim 7
Dependent Claim 25 words
The process of claim 1 wherein said organic sovent is present in amounts of about 5 to 75 percent by weight of the reaction mixture.
Claim 8
Dependent Claim 14 words
A dye in powder form made in accordance with the process of claim 1.
Claim 9
Dependent Claim 251 words
A process for producing a lyophilized dyestuff for coloring keratinic fibers consisting essentially of reacting hydrogen peroxide with an oxidation base in an aqueous alkaline solution open to ambient atmosphere in the presence of a coupler selected from the group consisting of metaphenylene diamine, 2,4-diamino anisole, 2,4-diamino toluene, metaaminophenol, 6-methyl-3-aminophenol, N-methyl metaaminophenol, 4-methoxy-3-aminophenol, resorcin, 2,6-xylenol, α-naphthol, 3-methoxy-4-aminophenol and the sulfate, hydrochloride and hydrobromide thereof, the molar ratio of said coupling agent to said oxidation base before oxidation being between 0:1 and 10:1 and in the presence of an organic solvent for the resulting dyestuff, said organic solvent being selected from the group consisting of tert-butyl alcohol, dimethyl sulfoxide, dioxane and benzyl alcohol and having a pH ranging from 8 to 13 at a temperature between about 15°-30°C for a period of about 5 minutes to 30 hours and lyophilizing said reaction mixture, the molar ratio of said hydrogen peroxide to said oxidation base being between about 0.1:1 to 20:1, said oxidation base being selected from the group consisting of paratoluylene diamine, paraphenylene diamine, N,N-dimethyl paraphenylene diamine, methyl paraphenylene diamine, chloroparaphenylene diamine, 2-methoxy-5-methyl paraphenylene diamine, 2,6-dimethyl-3-methoxy paraphenylene diamine, tetramethyl paraphenylene diamine, 2-methoxy paraphenylene diamine, para aminophenol, 2,6-dimethyl para aminophenol, 2,4-diamino anisole, 2-methyl para aminophenol, 1-methoxy-2,5-dimethyl paraphenylene diamine and the hydrochlorides thereof, wherein lyophilizing said reaction mixture comprises freezing said reaction mixture at a temperature of about -200° to -60°C and subliming said frozen mixture at a temperature of about -50° to -30°C at a pressure of about 0.01 to 0.1 mm Hg.
Claim 10
Dependent Claim 251 words
A process for producing a lyophilized dyestuff for coloring keratinic fibers consisting essentially of reacting hydrogen peroxide with an oxidation base in an aqueous alkaline solution open to ambient atmosphere in the presence of a coupler selected from the group consisting of metaphenylene diamine, 2,4-diamino anisole, 2,4-diamino toluene, metaaminophenol, 6-methyl-3-aminophenol, N-methyl metaaminophenol, 4-methoxy-3-aminophenol, resorcin, 2,6-xylenol, α-naphthol, 3-methoxy-4-aminophenol and the sulfate, hydrochloride and hydrobromide thereof, the molar ratio of said coupling agent to said oxidation base before oxidation being between 0:1 and 10:1 and in the presence of an organic solvent for the resulting dyestuff, said organic solvent being selected from the group consisting of tert-butyl alcohol, dimethyl sulfoxide, dioxane and benzyl alcohol and having a pH ranging from 8 to 13 at a temperature between about 15°-30°C for a period of about 5 minutes to 30 hours and lyophilizing said reaction mixture, the molar ratio of said hydrogen peroxide to said oxidation base being between about 0.1:1 to 20:1, said oxidation base being selected from the group consisting of paratoluylene diamine, paraphenylene diamine, N,N-dimethyl paraphenylene diamine, methyl paraphenylene diamine, chloroparaphenylene diamine, 2-methoxy-5-methyl paraphenylene diamine, 2,6-dimethyl-3-methoxy paraphenylene diamine, tetramethyl paraphenylene diamine, 2-methoxy paraphenylene diamine, para aminophenol, 2,6-dimethyl para aminophenol, 2,4-diamino anisole, 2-methyl para aminophenol, 1-methoxy-2,5-dimethyl paraphenylene diamine and the hydrochlorides thereof, wherein lyophilizing said reaction mixture comprises freezing said reaction mixture at a temperature of about -200° to -60°C and subliming said frozen mixture at a temperature of about -50° to -30°C at a pressure of about 0.01 to 0.1 mm Hg.
Claim 11
Dependent Claim 24 words
The process of claim 8 wherein the molar ratio of said coupling agent to said oxidation base before oxidation is between 0:1 to 2:1.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-09-21 1980-03-22 1980-09-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-09-21 1984-03-22 1984-09-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-09-21 1988-03-22 1988-09-21 $7700.00 Window Closed / Lapsed

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