# US 5,702,712 A · Melanoquaternary compounds and their use as hair dyes and for skin treatment

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- Number: US 5,702,712 A
- Document ID: US5702712A
- Status: Granted
- Kind: A
- Application number: 08/568,056
- Filed: 1995-12-06
- Granted: 1997-12-30
- Earliest claimed: 1995-12-06
- Assignees: Clairol Incorporated
- Inventors: Gottfried Wenke; Giuseppe Prota
- Web page: https://patentgrep.com/patent/US5702712A

## CPC

- A61K 8/416: {Quaternary ammonium compounds (A61K8/35 takes precedence)}
- A61K 8/492: {having condensed rings, e.g. indol}
- A61K 8/72: containing organic macromolecular compounds
- A61Q 5/065: {Preparations for temporary colouring the hair, e.g. direct dyes}
- A61Q 5/10: Preparations for permanently dyeing the hair
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- A61Q 19/04: for chemically tanning the skin (topical sun or radiation screening or tanning preparations A61Q17/04)
- A61K 2800/57: Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

Water soluble, cationic products useful as hair colorants or for the treatment of skin which are esters or amides formed by reaction of melanin and a quaternary salt containing a reactive amino or hydroxyl group, as well as compositions containing them and methods of using such products to color hair or treat skin are described.

## Claims

### Claim 1

A water soluble compound having the formula: ##STR2## wherein M is a melanin residue,
Y is --O-- or --NH,
n is an integer from 1 to 20,
R.sub.1, R.sub.2 R.sub.3 which may be the same or different are substituted or unsubstituted alkyl groups haing from 1 to 22 carbon atoms, the alkyl substituent being selected from the group consisting of halo, cyano, and nitro,
m is the number of derivatized carboxyl groups in the melanin residue, and
X is an anion.

### Claim 2 (depends on 1)

The compound of claim 1 in which n is 6 to 15.

### Claim 3 (depends on 1, 2)

The compound of claim 1 or 2 in which at least one of R.sub.1, R.sub.2 and R.sub.3 having 1 to 22 carbon atoms and up to two of R.sub.1, R.sub.2 and R.sub.3 contains 1 to 6 carbon atoms.

### Claim 4 (depends on 3)

The compound of claim 3 in which one of R.sub.1, R.sub.2 and R.sub.3 having 12 to 16 carbon atoms and two of R.sub.1, R.sub.2 and R.sub.3 having 1 to 6 carbon atoms.

### Claim 5

A composition with a pH of from about 3 to about 10 for coloring hair or treating skin containing:
(a) a compound having the formula: ##STR3## wherein M is a melanin residue,
Y is --O-- or --NH,
n is an integer from 1 to 20,
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,
m is the number of derivatized carboxyl groups in the melanin residue, and
X is an anion,
said compound (a) being present in the composition in an amount effective to color hair or treat skin, and
(b) a cosmetically acceptable carrier.

### Claim 6 (depends on 5)

The composition of claim 5 in which n is 6 to 15.

### Claim 7 (depends on 5, 6)

The composition of claim 5 or 6 in which at least one or R.sub.1, R.sub.2 and R.sub.3 contains 1 to 22 carbon atoms and up to two of R.sub.1, R.sub.2 and R.sub.3 having 1 to 6 carbon atoms.

### Claim 8 (depends on 7)

The composition of claim 7 in which one or R.sub.1, R.sub.2 and R.sub.3 having 12 to 16 carbon atoms and two of R.sub.1, R.sub.2 and R.sub.3 having 1 to 6 carbon atoms.

### Claim 9 (depends on 5)

The hair colorant composition of claim 5 additionally containing a surfactant in an amount of from about 1% to about 50%.

### Claim 10 (depends on 9)

The composition of claim 9 in which at least one or R.sub.1, R.sub.2 and R.sub.3 having 1 to 22 carbon atoms and up to two of R.sub.1, R.sub.2 and R.sub.3 having 1 to 6 carbon atoms.

### Claim 11 (depends on 10)

The composition of claim 10 in which one or R.sub.1, R.sub.2 and R.sub.3 having 12 to 16 carbon atoms and two of R.sub.1, R.sub.2 and R.sub.3 having 1 to 6 carbon atoms.

### Claim 12 (depends on 10)

The composition of claim 10 in which one or R.sub.1, R.sub.2 and R.sub.3 having 1 to 22 carbon atoms and two of R.sub.1, R.sub.2 and R.sub.3 having 1 to 6 carbon atoms.

### Claim 13 (depends on 10)

The composition of claim 10 in which at least one or R.sub.1, R.sub.2 and R.sub.3 having 12 to 16 carbon atoms and up to two of R.sub.1, R.sub.2 and R.sub.3 having 1 to 6 carbon atoms.

### Claim 14

A method of coloring hair which comprises contacting hair with an effective hair dyeing amount of a compound of the formula: ##STR4## wherein M is a melanin residue,
Y is --O-- or --NH,
n is an integer from 1 to 20,
R.sub.1, R.sub.2 and R.sub.3 which may be the same or different are substitued 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,
m is the number of derivatized carboxyl groups in the melanin residue, and
X is an anion.

### Claim 15 (depends on 5)

The hair colorant composition of claim 5 wherein the compound (I) is present in an amount of from about 0.1 to 5% by weight of the composition.

### Claim 16 (depends on 5)

The skin treatment composition of claim 5 wherein compound (I) is present in an amount of from 0.01 to 10% by weight of the composition.