Hair dye composition and process for using the same

• US 4,746,322 A
• Filed: 05/11/1987
• Issued: 05/24/1988
• Est. Priority Date: 04/09/1984
• Status: Expired due to Fees

• Current Assignee: Repligen Corporation
• Original Assignee: Repligen Corporation
• Inventors: Herlihy, Walter C.
• Primary Examiner(s): Meyers, Albert T.
• Assistant Examiner(s): NOT, DEFINED
• Application Number:
  US07/052,172
• Time in Patent Office: 379 Days
• Field of Search: 8/405, 8/406, 8/407, 8/412, 8/428
• US Class Current: 8/405
• CPC Class Codes: A61K 8/347 Phenols
• CPC Class Codes: A61K 8/44 Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
• CPC Class Codes: A61Q 5/065 Preparations for temporary colouring the hair, e.g. direct dyes
• CPC Class Codes: D06P 3/08 using oxidation dyes

Abstract

The subject invention concerns novel dye compositions and a process for dyeing keratinous fibers, for example, hair, to give a pleasing and stable colored product. The dye composition is a novel combination of three elements to give a dye that, unexpectedly, has highly desirable dyeing properties. This unique combination comprises (1) a suitable organic compound to assist dye dispersion, (2) dye precursors including dopamine, D-dopa, L-dopa, D,L-dopa, or analogs thereof, and (3) iodate or periodate. Desired color variations can be obtained by the use of appropriate color modifiers.

Claims

1. An aqueous dye composition for dyeing hair which does not dye the skin comprising:

(1) at least one water soluble dye precursor of the formula ##STR3## wherein R₁, R₂ can be the same or different and are;

H, alkyl or 1-4C, NH₂, OH, COOR'"'"' wherein R'"'"' is alkyl of 1-4C or H, CONH₂, halogen, OR" wherein R" is alkyl of 1-4C, CH₂ OH, CH₂ NH₂, CONR'"'"'R" wherein R'"'"' and R" can be the same or different;

R₃ is H or alkyl of 1-4C or COR";

R₄, R₅ can be the same or different and are;

H, alkyl of 1-4C, NH₂, OH, COOH, CONH₂, halogen, OR", NO₂, SO₃, HNR", or NR"R";

(2) an alkali metal or alkaline earth metal salt of iodate or periodate;

(3) at least one organic dye dispersing agent that is compatible with the dye precursor used and will not react with the iodate or periodate oxidant; and

(4) water.

2. A dye composition, according to claim 1, wherein said dye precursor has the formula ##STR4## wherein R₁, R₂ can be the same or different and are:

H, CH₃, C₂ H₅, OH, or halogen;

R₃ is H, CH₃ or C₂ H₅ ;

R₄, R₅ can be the same or different and are as defined in claim 1.

3. A dye composition, according to claim 1, wherein said dye precursor is dopamine, D-dopa, L-dopa, or D,L-dopa.

4. A dye composition, according to claim 1, wherein said dye dispersing agent is selected from the group consisting of 2-isopropyl 5-methyl phenol, acetophenone, 4-ethyl acetophenone, cyclohexanone, 2,4-dimethyl acetophenone, 3,5-dimethyl cyclohexanone, 4-methyl cyclohexanone, ethylbenzoate, benzyl acetate, benzyl propionate, benzyl butyrate, cyclohexanol, 2-methyl cyclohexanol, furfuryl alcohol, hexanol, 2-methyl-1-pentanol, benzyl alcohol, α

,α

,dimethyl benzyl alcohol, α

-propyl benzyl alcohol, DL-α

methyl benzyl alcohol, 2-benzyloxyethanol, 2-benzyloxypropanol, 2-benzyloxybutanol, ethylene glycol phenyl ether, butyrolactone, 1,2-propylene glycol carbonate, ethylene carbonate, tetramethylene sulfone, butadiene sulfone, tetrahydro thiophene dioxide, 1-n-dodecylazacycloheptan-2-one, and ethylene glycol sulfite.

5. A dye composition, according to claim 1, wherein said hair is gray or white hair.

6. A dye composition, according to claim 1, wherein said dye dispersing agent is present at a concentration of about 0.1 to about 30 wt/vol%;

said dye precursor is at a concentration of about 0.1 to about 10 wt/vol% to the dye composition; and

said alkali metal or alkaline earth metal salt of iodate or periodate is at a concentration of about 0.1 to about 5 wt/vol%.

7. A dye composition, according to claim 1, wherein a thickener is present to minimize dripping from the hair.

8. A dye composition, according to claim 7, wherein said thickener is polyethylene glycol-150 distearate.

9. A dye composition, according to claim 1, wherein a color modifier, or a mixture thereof, selected from the group consisting of 4-methylcatechol, 3,4-dihydroxybenzoic acid, 3,4-dihydroxybenzaldehyde, 4-bromocatechol, catechol, 4-methoxycatechol, m-aminophenol, resorcinal, cysteine, glutathione, mercaptoacetic acid, and lysine is present.

10. A dye composition, according to claim 9, wherein said color modifier is catechol or cysteine.

11. A dye composition, according to claim 1, wherein potassium or ammonium persulfate is present.

12. A dye composition, according to claim 1, wherein a stabilizer is present if the dopamine dye precursor is in solution.

13. A dye composition, according to claim 1, wherein said dye dispersing agent is benzyl alcohol.

14. A dye composition, according to claim 1, wherein said dye dispersing agent is ethylene carbonate.

15. A process for dyeing hair which does not dye the skin and which comprises contacting hair with a dye composition comprising:

(1) at least one water soluble dye precursor of the formula ##STR5## wherein R₁, R₂ can be the same or different and are;

H, alkyl of 1-4C, NH₂, OH, COOR'"'"' wherein R'"'"' is alkyl of 1-4C or H, CONH₂, halogen, OR" wherein R" is alkyl of 1-4C, CH₂ OH, CH₂ NH₂, CONR'"'"'R" wherein R'"'"' and R" can be the same or different;

R₃ is H or alkyl or 1-4C or COR";

R₄, R₅ can be the same or different and are;

H, alkyl of 1-4C, NH₂, OH, COOH, CONH₂, halogen, OR", NO₂, SO₃, HNR", or NR"R";

(2) an alkali metal or alkaline earth metal salt of iodate or periodate;

(3) at least one organic dye dispersing agent that is compatible with the dye precursor used and will not react with the iodate or periodate oxidant; and

(4) water for about 20 min to about 60 min, and rinsing the dyed hair.

16. A process, according to claim 15, wherein said dye dispersing agent is selected from the group consisting of 2-isopropyl 5-methyl phenol, acetophenone, 4-ethyl acetophenone, cyclohexanone, 2,4-dimethyl acetophenone, 3,5-dimethyl cyclohexanone, 4-methyl cyclohexanone, ethylbenzoate, benzyl acetate, benzyl propionate, benzyl butyrate, cyclohexanol, 2-methyl cyclohexanol, furfuryl alcohol, hexanol, 2-methyl-1-pentanol, benzyl alcohol, α

,α

,dimethyl benzyl alcohol, α

-propyl benzyl alcohol, DL-α

methyl benzyl alcohol, 2-benzyloxyethanol, 2-benzyloxypropanol, 2-benzyloxybutanol, ethylene glycol phenyl ether, butyrolactone, 1,2-propylene glycol carbonate, ethylene carbonate, tetramethylene sulfone, butadiene sulfone, tetrahydro thiophene dioxide, 1-n-dodecylazacycloheptan-2-one, and ethylene glycol sulfite.

17. A process, according to claim 15, wherein said dye composition comprises

(1) said dye precursor at a concentration of about 0.1 to about 10 wt/vol% to the dye composition;

(2) said alkali metal or alkaline earth metal salt of an iodate or periodate at a concentration of about 0.1 to about 5 wt/vol%; and

(3) said dye dispersing agent at a concentration of about 0.1 to about 30 wt/vol%.

18. A process, according to claim 15, wherein said dye precursor is dopamine, D-dopa, L-dopa, or D,L-dopa.

19. A process, according to claim 15, wherein a thickener to minimize dripping from the hair is added to the dye composition.

20. A process, according to claim 19, wherein said thickener is polyethylene glycol-150 distearate.

21. A process, according to claim 15, wherein a color modifier, or a mixture thereof, selected from the group consisting of 4-methylcatechol, 3,4-dihydroxybenzoic acid, 3,4-dihydroxybenzaldehyde, 4-bromocatechol, catechol, 4-methoxycatechol, m-aminophenol, resorcinol, cysteine, glutathione, mercaptoacetic acid, and lysine is added to the dye composition.

22. A process, according to claim 21, wherein said color modifier is catechol or cysteine.

23. A process, according to claim 15, wherein a stabilizer is added to the dye composition if the dopamine dye precursor is in solution.

24. A process, according to claim 15, wherein said dye dispersing agent is benzyl alcohol.

25. A process, according to claim 15, wherein said dye dispersing agent is ethylene carbonate.