Coloring agents and methods of use thereof

1. A functionalized dye comprising at least one chromophore and a color fastness moiety, wherein the chromophore is bound to the color fastness moiety by a linker, wherein said dye is a compound of formula Ia:

C-L-F  (Ia)

wherein

C is a chromophore selected from the following group: a diarylmethane chromophore, an azo chromophore, a nitro chromophore, a nitroso chromophore, or a substituted benzene chromophore;

linker L is of formula (IIIa):

wherein

L covalently links C via the left hand side of formula IIIa to F via the right hand side of formula IIIa;

a, b, c, d, and e are each 0;

f is 1;

R 40 , R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , and R 49 are absent;

R 50 and R 51 are each hydrogen;

E is NR 52 or NR 53 C═O;

R 52 and R 53 are each independently hydrogen or alkyl;

F is a color fastness moiety represented by formula Va:

wherein

m is 0 or 1;

n and o are 0;

p, q and r are each independently 0 or 1, provided that at least one of m, p, q and r is not 0;

R 78 , R 79 , R 84 , R 85 , R 87 , R 88 and R 89 are each hydrogen;

R 80 , R 81 , R 82 , and R 83 are absent;

R 86 is absent, hydrogen or hydroxyl;

K is NR 90 , or C(═O)NR 92 ;

W is NR 95 R 96 , CR 97 R 98 R 99 or OR 100 ;

R 90 is hydrogen;

R 92 is hydrogen or alkyl;

R 95 is alkyl and R 96 is hydrogen or alkyl, or R 95 and R 96 , together with the nitrogen to which they are attached are linked to form a 4-8-membered heterocyclic ring comprising 1-3 heteroatoms;

R 97 , R 98 and R 99 are hydrogen, hydroxyl, alkyl, alkoxy or heteroaryl; and

R 100 is hydrogen or alkyl; provided that the dye of formula Ia is not:

or a cosmetically acceptable salt thereof.

2. The dye of claim 1 , wherein E is NR 52 and K is C(═O)NR 92 .

3. The dye of claim 1 , wherein E is NR 52 and K is NR 90 .

4. The dye of claim 1 , wherein E is NR 53 C═O and K is NR 90 .

5. The dye of claim 1 , wherein m is 0.

6. The dye of claim 1 , wherein m is 1.

7. The dye of claim 1 , wherein p, q, and r are 1.

8. The dye of claim 1 , wherein p and q are 1 and r is 0.

9. The dye of claim 1 , wherein p, q, and r are 0.

10. The dye of claim 1 , wherein R 86 is hydroxyl.

11. The dye of claim 1 , wherein W is NR 95 NR 96 , and R 95 and R 96 are each alkyl optionally substituted with hydroxy.

12. The dye of claim 1 , wherein W is NR 95 R 96 ; and R 95 and R 96 are linked to form a ring.

13. The dye of claim 1 , wherein W is CR 97 R 98 R 99 ; R 97 is hydrogen; and R 98 and R 99 are each alkoxy.

14. The dye of claim 1 , wherein W is CR 97 R 98 R 99 ; R 97 is hydrogen; and R 98 and R 99 are each alkyl optionally substituted with hydroxy.

15. The dye of claim 1 , wherein W is CR 97 R 98 R 99 ; R 97 and R 98 are hydrogen; and R 99 is alkyl optionally substituted with hydroxy.

16. The dye of claim 1 , wherein W is CR 97 R 98 R 99 ; R 97 and R 98 are hydrogen; and R 99 is heteroaryl.

17. The dye of claim 1 , wherein W is CR 97 R 98 R 99 ; R 97 and R 98 are each hydrogen; and R 99 is hydroxyl.

18. The dye of claim 1 , wherein W is OR 100 ; and R 100 is hydrogen.

19. The dye of claim 1 , wherein the dye is a non-oxidative dye.

20. The dye of claim 1 , wherein the functionalized dye has greater color fastness compared to a non-functionalized direct dye.

21. A dye composition comprising at least one dye of claim 1 and a medium suitable for dyeing keratin fibers.

22. A method for coloring hair comprising applying to said hair a dye composition comprising at least one dye of claim 1 , such that said hair is colored.

23. A kit comprising a dye composition comprising at least one dye of claim 1 and instructions for use.

24. A method for coloring hair comprising the steps of

a) treating the hair with an oxidative dye in the presence of ammonia and optionally hydrogen peroxide for between about 1 and about 60 minutes;

b) optionally rinsing the hair; and optionally partially drying the hair;

c) treating the hair with a dye composition comprising at least one dye of claim 1 for between about 1 and about 60 minutes; and

d) rinsing the hair.

25. The method of claim 24 further comprising one or more of the following steps:

e) washing the hair with shampoo; and/or conditioning the hair with conditioner after rinsing the hair;

f) rinsing the hair; and

g) optionally drying the hair.

26. The dye of claim 1 , wherein the chromophore is a diarylmethane chromophore.

27. The dye of claim 1 , wherein the chromophore is an azo chromophore.

28. The dye of claim 27 , wherein the chromophore is selected from the following structural formulas:

wherein:

R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7g , R 7h , R 7i and R 7j are each independently hydrogen, hydroxyl, alkyl, amino, alkoxy, halogen, acyl, —NO 2 , or —CN, or are attached to linker L;

R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , R 8g , R 8h , R 8i , R 8j , R 8k and R 8l are each independently hydrogen, hydroxyl, alkyl, amino, alkoxy, halogen, acyl, —NO 2 , or —CN, or are attached to linker L;

R 9a , R 9b , R 9c , R 9d , R 9e , R 9f , R 9g , R 9h , R 9i , R 9j , R 9k and R 9l are each independently hydrogen, hydroxyl, alkyl, amino, alkoxy, halogen, acyl, —NO 2 , or —CN, or are attached to linker L;

R 10a , R 10b , R 10c , R 10d , R 10e , R 10f , R 10g , R 10h , R 10i , R 10j , R 10k , R 10l , R 10m and R 10n are each independently hydrogen, hydroxyl, alkyl, amino, alkoxy, halogen, acyl, —NO 2 , or —CN, or are attached to linker L;

R 11a , R 11b , R 11c , R 11d , R 11e , R 11f , R 11g , R 11h , R 11i , R 11j , R 11k , R 11l and R 11m are each independently hydrogen, hydroxyl, alkyl, aryl, amino, alkoxy, halogen, acyl, —NO 2 , or —CN, or are attached to linker L;

R 11k is hydrogen, hydroxyl, alkoxy, alkyl, acyl or is attached to linker L; and

R 13a , R 13b , R 13c , R 13d , R 13e , R 13f , R 13g , R 13h , R 13i , R 13j , R 13k and R 13l are each independently hydrogen, hydroxyl, alkyl, amino, alkoxy, halogen, acyl, —NO 2 , or —CN, or are attached to linker L;

or a cosmetically acceptable salt of any of the foregoing thereof.

29. The dye of claim 1 , wherein the chromophore is a nitro chromophore.

30. The dye of claim 1 , wherein the chromophore is a nitroso chromophore.

31. The dye of claim 1 , wherein the chromophore is a substituted benzene chromophore.

32. The dye of claim 1 , wherein the chromophore is of the following structural formula:

wherein

R 26a is attached to linker L; and R 26b , R 26c , R 26d , R 26e and R 26f are each independently hydrogen, ydroxyl, amino, alkoxy, alkyl optionally substituted with ydroxyl, CF 3 , CN, halogen, NO 2 , SO 3 H, aminocarbonyl, carbonyl, or alkoxycarbonyl, or a cosmetically acceptable salt thereof.

33. The dye of claim 32 , wherein R 26b is —NO 2 ; R 26c , R 26e and R 26f are hydrogen; R 26d is hydrogen or NH 2 .

34. the dye of claim 1 , wherein the dye is selected from one of the following:

or a cosmetically acceptable salt of any of the foregoing thereof.