Method of coloring hair with washfast blue imidazolium direct dye compounds

Patent metadata

Field	Value
Publication number	US-10034823-B2
Application number	US-201615267585-A
Country	US
Kind code	B2
Filing date	Sep 16, 2016
Priority date	Sep 16, 2016
Publication date	Jul 31, 2018
Grant date	Jul 31, 2018

Abstract

Described herein is a method of dyeing the hair. The method includes applying to the hair a hair color composition including one or more direct dye compounds and rinsing the hair with water. The one or more direct dye compounds each include a blue-violet or blue chromophore, one or two permanent cations, one to four incipient cations, and one or more hydrophobic moieties. The incipient cations are pendant to the core structure and are neutral. The direct dye compounds enter the hair shaft after the hair color composition is applied to the hair. The hair color composition has a pH of from about 6 to about 11. The pH of the hair after rinsing is from about 3.5 to about 6. The rinsing of the hair causes one or more of the one to four incipient cations to change from neutral to positively charged inside of the hair shaft.

First claim

What is claimed is:

1. A method of dyeing the hair, the method comprising:
a. applying to the hair a hair color composition comprising one or more direct dye compounds, the one or more direct dye compounds each comprising:
i. a blue-violet or blue chromophore;
ii. one or two permanent cations, wherein the permanent cations are pendant to the chromophore or part of the chromophore, and wherein the chromophore and the permanent cations form a core structure; and
iii. one to four incipient cations, wherein each of the one to four incipient cations is pendant via a linker group to the core structure, and wherein the incipient cations are neutral,
iv. one or more C2-C9 hydrophobic moieties, wherein the one or more C2-C9 hydrophobic moieties are pendant to the core structure;

wherein the one or more direct dye compounds enter the hair shaft after the hair color composition is applied to the hair; and
wherein the hair color composition has a pH of from about 6 to about 11;
b. rinsing the hair with water;
wherein the pH of the hair after rinsing is from about 3.5 to about 6; and
wherein the rinsing of the hair causes one or more of the one to four incipient cations to change from neutral to positively charged inside of the hair shaft,

wherein the chromophore has a structure according to Formula (X), or a tautomer or salt thereof,

wherein
(i) R 1g , R 1h , R 1j , R 1k , R 1m , R 1n , R 1p and R 1r are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying a quaternary ammonium cation, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether, thiol with or without a linker group, alkylsulfonate, alkylsulfate, carboxylalkyl, acrylamide or substituted acrylamides with or without a linker group, vinylsulfone with or without a linker group, sulfonyl ethyl sulfate with or without a linker group, halo-s-triazines with or without a linker group, halopyrimidines with or without a linker group, or haloquinoxalines with or without a linker group;
(ii) R 1b , R 1c , R 1e and R 1t are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying a quaternary ammonium cation, alkoxy, aryloxy, acyl, halogen, a heterocyclic moiety, thioether, thiol with a linker group, alkylsulfonate, alkylsulfate, carboxylalkyl, acrylamide or substituted acrylamides with a linker group, vinylsulfone with a linker group, sulfonyl ethyl sulfate with a linker group, halo-s-triazines with a linker group, halopyrimidines with a linker group, or haloquinoxalines with a linker group;
(iii) R 1f and R 1s are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying a quaternary ammonium cation, acyl, a heterocyclic moiety, thioether, thiol with a linker group, alkylsulfonate, alkylsulfate, carboxylalkyl, acrylamide or substituted acrylamides with a linker group, vinylsulfone with a linker group, sulfonyl ethyl sulfate with a linker group, halo-s-triazines with a linker group, halopyrimidines with a linker group, or haloquinoxalines with a linker group;
(iv) R 1a and R 1d are each independently alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying a quaternary ammonium cation, alkyl group carrying a quaternary ammonium cation, thioether, thiol with a linker group, alkylsulfonate, alkylsulfate, carboxylalkyl, acrylamide or substituted acrylamides with a linker group, vinylsulfone with a linker group, sulfonyl ethyl sulfate with a linker group, halo-s-triazines with a linker group, halopyrimidines with a linker group, or haloquinoxalines with a linker group; and
(v) X and Y are each independently an oxygen or a nitrogen atom; wherein in the case where X and/or Y is oxygen atom, the corresponding group attached to the oxygen atom, R 1f and/or R 1s , ceases to exist.

2. The method of claim 1 , wherein at least one of X and Y is an oxygen atom.

3. The method of claim 1 , wherein the hair color composition further comprises from about 0.1% to about 20%, by weight of the composition, of at least one oxidizing agent.

4. A method of dyeing the hair, the method comprising:
a. applying to the hair a hair color composition comprising one or more direct dye compounds, the one or more direct dye compounds each comprising:
i. a blue-violet or blue chromophore;
ii. one or two permanent cations, wherein the permanent cations are pendant to the chromophore or part of the chromophore, and wherein the chromophore and the permanent cations form a core structure; and
iii. one to four incipient cations, wherein each of the one to four incipient cations is pendant via a linker group to the core structure, and wherein the incipient cations are neutral;
iv. one or more C2-C9 hydrophobic moieties, wherein the one or more C2-C9 hydrophobic moieties are pendant to the core structure;

wherein the one or more direct dye compounds enter the hair shaft after the hair color composition is applied to the hair; and
wherein the hair color composition has a pH of from about 6 to about 11;
b. rinsing the hair with water;
wherein the pH of the hair after rinsing is from about 3 to about 6; and
wherein the rinsing of the hair causes one or more of the one to four incipient cations to change from neutral to positively charged inside of the hair shaft,

wherein the chromophore has a structure according to Formula (XI), or a tautomer or salt thereof,

wherein
(i) R 2h , R 2j , R 2k and R 2m are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying a quaternary ammonium cation, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether, thiol with or without a linker group, alkylsulfonate, alkylsulfate, carboxylalkyl, acrylamide or substituted acrylamides with or without a linker group, vinylsulfone with or without a linker group, sulfonyl ethyl sulfate with or without a linker group, halo-s-triazines with or without a linker group, halopyrimidines with or without a linker group, or haloquinoxalines with or without a linker group;
(ii) R 2b , R 2c , R 2e , R 2f and R 2p are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying a quaternary ammonium cation, alkoxy, aryloxy, acyl, halogen, a heterocyclic moiety, thioether, thiol with a linker group; alkylsulfonate, alkylsulfate, carboxylalkyl, acrylamide or substituted acrylamides with a linker group, vinylsulfone with a linker group, sulfonyl ethyl sulfate with a linker group, halo-s-triazines with a linker group, or halopyrimidines with a linker group, haloquinoxalines with a linker group;
(iii) R 2g and R 2h , are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying a quaternary ammonium cation, acyl, a heterocyclic moiety, thioether, thiol with a linker group, alkylsulfonate, alkylsulfate, carboxylalkyl; acrylamide or substituted acrylamides with a linker group, vinylsulfone with a linker group, sulfonyl ethyl sulfate with a linker group, halo-s-triazines with a linker group, halopyrimidines with a linker group, or haloquinoxalines with a linker group;
(iv) R 2a and R 2d are each independently alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying

Assignees

• Noxell Corp

Inventors

• Murphy Bryan Patrick
• Zhang Guiru
• Zhao Jielu

Classifications

• C09B29/0051

  containing a six-membered heterocyclic ring with two nitrogen atoms · CPC title

• A61K2800/4324

  in preparations for permanently dyeing the hair · CPC title

• A61Q5/10

  Preparations for permanently dyeing the hair · CPC title

• A61K8/4946 Primary

  Imidazoles or their condensed derivatives, e.g. benzimidazoles · CPC title

• C09B29/0037

  containing a five-membered heterocyclic ring with two nitrogen atoms · CPC title