Synthesis of quaternary melanin compounds and their use as hair dyes or for skin treatment
AssigneeClairol Incorporated
InventorsGottfried Wenke, Giuseppe Prota
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Abstract
The specification describes water soluble, cationic products useful as hair colorants or for skin care obtained by oxidative polymerization of a 5,6-dihydroxyindole-2-quaternary amides or esters, as well as compositions containing the same, methods of using the same in compositions to color hair or treat skin and intermediates for producing the products.
Claims19
A water soluble cationic compound obtained by oxidative polymerization of a 5,6-dihydroxindole carboxylic acid ester or amide of the formula:
- ##STR3## wherein:
- Y is --O-- or ##STR4## n is an integer from 1 to 20 R is hydrogen or alkyl having from 1 to 6 carbon atoms
- R.sub.1, R.sub.2 and R.sub.3 which may be the same or different are substituted or unsubstituted alkyl groups having from 1 to 22 carbon atoms, the alkyl substituent being selected from the group consisting of halo, cyano and nitro, and
- X is an anion.
A composition with a pH of from about 3 to about 10 for coloring hair or skin care containing (a) a compound obtained by oxidative polymerization of a 5,6-dihydroxindole carboxylic acid ester or amide of the formula:
- ##STR5## wherein:
- Y is --O-- or ##STR6## n is an integer from 1 to 20 R is hydrogen or alkyl having from 1 to 6 carbon atoms
- R.sub.1, R.sub.2 and R.sub.3 which my be the same or different are substituted or unsubstituted alkyl groups having from 1 to 22 carbon atoms, the alkyl substituent being selected from the group consisting of halo, cyano and nitro, and
- X is an anion;
- said compound being present in the composition in an amount effective to color hair or treat skin, and (b) a cosmetically acceptable carrier.
A compound of the formula:
- ##STR7## wherein:
- Y is --O-- or ##STR8## n is an integer from 1 to 20 R is hydrogen or alkyl having from 1 to 6 carbon atoms
- R.sub.1, R.sub.2 and R.sub.3 which may be the same or different are substituted or unsubstituted alkyl groups having from 1 to 22 carbon atoms, the alkyl substituent being selected from the group consisting of halo, cyano and nitro, and
- X is an anion.
A method of coloring hair which comprises contacting the hair with the product resulting from oxidatively polymerizing an intermediate of the formula:
- ##STR9## wherein:
- Y is --O-- or ##STR10## n is an integer from 1 to 20 R is hydrogen or alkyl having from 1 to 6 carbon atoms
- R.sub.1, R.sub.2 and R.sub.3 which may be the same or different are substituted or unsubstituted alkyl groups having from 1 to 22 carbon atoms the alkyl substituent being selected from the group consisting of halo, cyano, and nitro, and
- X is an anion.
Dependencies are inferred from the claim text.