Method of coloring hair with washfast yellow imidazolium direct dye compounds

Patent metadata

Field	Value
Publication number	US-9918919-B1
Application number	US-201615267560-A
Country	US
Kind code	B1
Filing date	Sep 16, 2016
Priority date	Sep 16, 2016
Publication date	Mar 20, 2018
Grant date	Mar 20, 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 yellow 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 one or more 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 7 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 yellow 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 yellow chromophore has a structure according to Formula V or a tautomer or salt thereof:

wherein
(i) R 1b , R 1c , and R 1f 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;
(ii) R 1a , R 1d , and R 1h are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying a quaternary ammonium cation, a heterocyclic moiety, 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
(iii) R 1e and R 1g are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyalkyl, aminoalkyl, alkyl group carrying a quaternary ammonium cation, a heterocyclic moiety, 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, or are attached to a polymer backbone through a linker, or part of a cyclic structure and joined by substituted or unsubstituted alkyl or heteroalkyl groups.

2. The method of claim 1 , wherein the one or more direct dye compounds each comprise two incipient cations.

3. The method of claim 1 , wherein the one or more direct dye compounds each has a molecular weight of less than about 1,000 g/mol.

4. The method of claim 1 , wherein the hair color composition has a pH of from about 9 to about 11.

5. The method of claim 1 , wherein the hair color composition has a pH of from about 6 to about 9.

6. The method of claim 1 , wherein an oxidizing agent is applied before or during the application of the hair color composition.

7. The method of claim 6 , wherein the oxidizing agent is selected from the group consisting of peroxides, perborates, percarbonates, persulfates, oxidant generating enzymes, oxidant generating substrates, and combinations thereof.

8. The method of claim 1 , wherein the hair color composition further comprises one or more oxidation dyes.

9. The method of claim 1 , wherein the hair color composition comprises at least one oxidation dye primary intermediate.

10. The method of claim 1 , wherein the hair color composition comprises at least one oxidation dye coupler.

11. The method of claim 1 , wherein the hair color composition further comprises at least 20%, by weight of the composition, water.

12. 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.

13. The method of claim 1 , wherein the hair color composition has a pH of from about 7 to about 11.

Assignees

• Noxell Coproration
• Noxell Corp

Inventors

• Murphy Bryan Patrick
• Zhang Guiru
• Garrett Garry Steven

Classifications

• A61K2800/4324

  in preparations for permanently dyeing the hair · CPC title

• A61Q5/10

  Preparations for permanently dyeing the hair · CPC title

• C09B29/0037

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

• A61K8/4946 Primary

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

• C09B44/12

  having one nitrogen atom as the only ring hetero atom · CPC title