Crosslinking of hair thiols

• US 4,793,993 A
• Filed: 08/24/1987
• Issued: 12/27/1988
• Est. Priority Date: 07/06/1987
• Status: Expired due to Term

• Current Assignee: Chesebrough-Pond's USA Company (Unilever PLC)
• Original Assignee: Chesebrough-Pond's USA Company (Unilever PLC)
• Inventors: Edelstein, Herbert, Siuta-Mangano, Patricia
• Primary Examiner(s): Lesmes, George F.
• Assistant Examiner(s): Ryan, P. J.
• Application Number:
  US07/088,356
• Time in Patent Office: 491 Days
• Field of Search: 424/70, 424/47, 424/71, 514/544, 514/569, 560/124, 560/132, 560/157, 560/169
• US Class Current: 424/70.2
• CPC Class Codes: A61K 2800/94 Involves covalent bonding to the substrate
• CPC Class Codes: A61K 8/40 containing nitrogen quinones containing nitrogen A61K8/355
• CPC Class Codes: A61K 8/4913 having five membered rings, e.g. pyrrolidone carboxylic acid
• CPC Class Codes: A61Q 5/04 Preparations for permanent waving or straightening the hair

Abstract

Keratinous material, such as human hair, in which disulfide linkages have been ruptured to form disulfide linkages can be set using diimidates, and disuccinimidyl compounds as disclosed herein.

Claims

1. A process for treating keratinous material in which the disulfide linkages have been disrupted to form free sulfhydryl groups which comprises:

contacting the keratinous material with a crosslinking reagent selected from the group consisting of (1) diimidates of the formula;

space="preserve" listing-type="equation">R.sub.1 --O--C(NH)--R--C(NH)--O--R.sub.1

and (2) disuccinimidyl compounds of the formula;

##STR2## and mixtures thereof, wherein R represents a connecting moiety and R₁ represents an alkyl of 1 to 10 carbons, at a temperature and pH to form crosslinkages and insufficient to substantially denature the protein of the keratlnous material.

2. The process as recited in claim 1 wherein the crosslinking is conducted at a pH between about 6 and about 9.

3. The process as recited in claim 1 wherein said keratinous material is human hair.

4. The process as recited in claim 3 wherein the hair is deformed to a desired shape prior to treatment with the crosslinking reagent.

5. The process as recited in claim 1 wherein said crosslinking reagent is water soluble.

17. The process as recited in claim 1 wherein the crosslinking reagent is the hydrochloride salt for water solubility.

18. The process as recited in claim 1 wherein said diimidate compound is selected from the group consisting of dimethyl suberimidate, dimethyl adipimidate, dimethyl pimelimidate and mixtures thereof.

20. The process as recited in claim 1 wherein said disuccinimidyl compound is ethylene glycol bis(sulfosuccinimidyl succinate).

21. A process of claim 1 wherein R is a divalent connecting radical selected from the group consisting of aliphatic, cycloaliphatic aromatic or combination thereof and wherein R can be substituted with carboxyl, sulfonic, amino, amido, hydroxyl and can contain ether and amine linkages.

6. A hair waving system comprising a composition for reducing disulfide bonds to form sulfhydral groups in hair and a crosslinking composition containing a crosslinking reagent selected from the group consisting of (1) diimidates of the formula:

space="preserve" listing-type="equation">Ri.sub.1 --O--C(NH)--R--C(NH)--O--R.sub.1

and

space="preserve" listing-type="equation">(2) disuccinimidyl compounds of the formula;

##STR3## and mixtures thereof, wherein R represents a connecting moiety and R.sub.1 represents an alkyl of 1 to 10 carbons.

7. The system as recited in claim 6 wherein said crosslinking reagent is water soluble.

19. The system as recited in claim 6 wherein said diimidate compound is selected from the group consisting of dimethyl suberimidate, dimethyl adipimidate, dimethyl pimelimidate and mixtures thereof.

22. A system of claim 6 wherein R is a divalent connecting radical selected from the group consisting of aliphatic, cycloaliphatic aromatic or combination thereof and wherein R can be substituted with carboxyl, sulfonic, amino, amido, hydroxyl and can contain ether and amine linkages.

8. A process for treating keratinous material in which the disulfide linkages have been disrupted by the action of a reducing agent forming free sulfhydryl groups comprising contacting the said keratinous material with a crosslinking reagent R₁ --O--C(NH)--R--C(NH)--O--R₁ wherein R represents a connecting moiety and R₁ represents an alkyl of 1 to 10 carbon atoms, the process being conducted under conditions sufficient to form crosslinkages and insufficient to substantially denature the protein of the keratinous material.

10. The process as recited in claim 8 wherein R is alkylene of 1 to 10 carbons.

11. The process as recited in claim 10 wherein R is alkylene of 4 to 6 carbons.

12. The process as recited in claim 8 wherein R₁ is an alkyl of 1 to 2 carbons.

14. The process as recited in claim 8 wherein said crosslinking reagent is water soluble.

23. A process of claim 8 wherein R is a divalent connecting radical selected from the group consisting of aliphatic, cycloaliphatic aromatic or combination thereof and wherein R can be substituted with carboxyl, sulfonic, amino, amido, hydroxyl and can contain ether and amine linkages.

9. A process for treating keratinous material in which the disulfide linkages have been disrupted by the action of a reducing agent forming free sulfhydryl groups comprising contacting the said keratinous material with a crosslinking reagent ##STR4## wherein R represents a connecting moiety, the process being conducted under conditions sufficient to form crosslinkages an insufficient to substantially denature the protein of the keratinous material.

13. The process as recited in claim 9 wherein R is alkyl of from 1 to 10 carbons.

15. The process as recited in claim 9 wherein said crosslinking reagent is water soluble.

16. The process as recited in claim 9 wherein the crosslinking reagent is sulfonated for water solubility.

24. A process of claim 9 wherein R is a divalent connecting radical selected from the group consisting of aliphatic, cycloaliphatic aromatic or combination thereof and wherein R can be substituted with carboxyl, sulfonic, amino, amide, hydroxyl and can contain ether and amine linkages.