DIRECT DYES AND COMPOSITION COMPRISING THE DYES

Abstract

The present invention relates to novel direct dyes and compositions comprising them for dyeing keratin fibers especially human hair. The novel dyes of the present invention have benzothiophene structure providing intensive and homogeneous dyeing on keratin fibers, especially human hair.

Claims

1. A compound according to the general structure ##STR00025## wherein R.sub.1 is H, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 hydroxyalkyl, COOH or COOR.sub.5 wherein R.sub.5 is C.sub.1-C.sub.4 alkyl, R.sub.2 is H or NR.sub.6R.sub.7 wherein R.sub.6 and R.sub.7 are same or different H, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4 hydroxyalkyl or acetyl, R.sub.3 is H, OH, NR.sub.6R or NHSO.sub.2R.sub.8 wherein R.sub.8 is NR.sub.6R alkyl or NR.sub.6R hydroxyalkyl, R.sub.4 is H, COOH or COOR.sub.5 and Hy is any heterocyclic group which is bound at a C atom to the diazo group and which may be substituted or unsubstituted.

2. The compounds according to claim 1 wherein Hy is selected from the group consisting of ##STR00026## ##STR00027## ##STR00028## wherein R.sub.9 is C.sub.1-C.sub.4 alkyl or C.sub.1-C.sub.4 hydroxyalkyl and “*” expresses position at which group binds to the diazo group, R.sub.21 to R.sub.50 independently represent hydrogen atom or a substituent which is selected from halogen atom, alkyl group, aryl group, hetero-ring group, cyano group, hydroxyl group, nitro group, alkoxy group, aryloxy group, amino group (including anilino group), acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio group, hetero-ring thio group, sulfamoyl group, alkylsulfonyl group, arylsulfonyl group, acyl group, alkoxycarbonyl group, and carbamoyl group; more preferably the substituent is halogen atom, alkyl group, cyano group, hydroxyl group, nitro group, alkoxy group, amino group (including anilino group), acylamino group, alkylsulfonylamino group, and carbamoyl group, “a, p, q, r, s” represent an integer of 0 to 4, “b, c” represent an integer of 0 to 6, “d, e, f, g, t, u” represent an integer of 0 to 3, “h, i, j, k, l, o” represent an integer of 0 to 2, “m” represent an integer of 0 to 1, when “a” to “u” represent an integer of 2 or more, groups represented by R21 to R50, which exist in a number of 2 or more, may be the same or different to each other.

3. The compounds according to claim 2 wherein the Hy is selected from the group consisting of (A-1), (A-5), (A-8), (A-9), (A-10), (A-11), (A-12), (A-13), (A-14), (A-15), (A-17), (A-19), (A-22), (A-23), (A-24), (A-25) and (A-26).

4. The compounds according to claim 1 wherein the compounds has the structure chosen from the group consisting of ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046##

5. The compounds according to claim 1 wherein the compounds are selected from D-1, D-2, D-3 and D4.

6. (canceled)

7. A composition characterized in that it comprises one or more of the compounds according to claim 1.

8. The composition according to claim 7 characterized in that it comprises one or more surfactants selected from anionic, nonionic, cationic and amphoteric ones.

9. The composition according to claim 7 characterized in that it comprises one or more cationic surfactant selected from the compounds or the general structure ##STR00047## where R12 is saturated or unsaturated, branched or straight alkyl chain with 8-22 C atoms or
R16 CO NH(CH2)n where R16 is saturated or unsaturated, branched or straight alkyl chain with 7-21 C atoms and n has typical value of 1-4 or
R16CO O(CH2)n where R16 is saturated or unsaturated, branched or straight alkyl chain with 7-21 C atoms and n has typical value of 1-4, and R13 is a saturated or unsaturated, branched or straight alkyl chain with 1-22 C atoms or
R16CO NH(CH2)n where R16 is saturated or unsaturated, branched or straight alkyl chain with 7-21 C atoms and n has typical value of 1-4 or
R16 CO O(CH2)n where R16 is saturated or unsaturated, branched or straight alkyl chain with 7-21 C atoms and n has typical value of 1-4, and R14 and R15 are independent from each other lower alkyl chain with 1 to 4 carbon atoms or ethoxy or propoxy group with number of ethoxy or propoxy groups varying in the range of 0 to 4, and X is chloride, bromide or methosulfate.

10. The composition according to claim 7 it comprises one or more hair conditioning compound, selected from cationic polymers, silicones, fatty alcohols, and conditioning oils.

11. The composition according to claim 7 characterized in that it comprises one or more organic solvent.

12. The composition according to claim 7 characterized in that it comprises one or more additional direct dyes, selected from anionic, cationic and nonionic ones.

13. The composition according to claim 7 characterized in that it comprises one or more oxidizing agent.

14. The composition according to claim 7 characterized in that it comprises one or more oxidative dye precursors and optionally one or more coupling agents

15. (canceled)

16. The compound according to claim 2 wherein the Hy is selected from the group consisting of A-10), (A-11), (A-12), (A-14), (A-22), (A-23), (A-25) and (A-26).

17. The compound according to claim 2 wherein the Hy is selected from the group consisting of (A-10), (A-23) and (A-26).

18. The compound according to claim 1 wherein the compound is selected from D2 and D3.

Description

EXAMPLE COMPOSITIONS-1

[0117]

TABLE-US-00001 % by weight active matter A B C D 2-propanol 5.00 5.00 5.00 5.00 Ammonia 1.25 1.25 1.25 1.25 Dyestuff I 0.40 — — — Dyestuff II — 0.40 — — Acid red 33 — — 0.40 — Acid red 52 — — — 0.40 Water to 100 to 100 to 100 to 100

[0118] The pH of the compositions A to D was adjusted with HCl to 10.

[0119] Method 1: Composition A to D was applied onto white goat hair for 30min at 30° C. Then the hair was rinsed, shampooed, dried and the dyeing result was determined colorimetrically by measuring L, a, and b values using a laboratory colorimeter. The Delta E values were calculated as the vectoral differences.

[0120] Method 2: Hair dyeing was carried out by applying the above composition after mixing with a 50% hydrogen peroxide comprising composition to produce an active hydrogen peroxide concentration of 3%, onto goat hair and being left on the hair for 30 min at 30° C. and rinsed off from hair with water and hair was shampooed and dried and the color was measured.

[0121] Method 3: Permed goat hair was dyed with the above compositions onto hair and after leaving the composition on the hair for 30 min at 30° C., the hair was rinsed off and shampooed and dried. The Color was measured with a laboratory colorimeter.

[0122] Following results were obtained:

TABLE-US-00002 Composition A B C D Method 1 70 71 49 49 Method 2 73 73 51 53 Method 3 71 74 69 76

[0123] From the above results it is clear that the compositions A and B colour hair tresses under non-oxidative (Method 1) and oxidative conditions (Method 2) in the same intensity. The hair tress damaged by means of permanent shaping treatment (Method 3) is also colored in the same intensity. On the other hand the compositions based on the existing dyes do show variability in coloring hair under oxidative condition and also color intensity on damaged hair is much stronger the natural hair which clearly indicates that hair comprising damaged parts may not be colored homogeneously with the known dyes but colored homogeneously with the novel dyes of the present inventions.

EXAMPLE COMPOSITIONS-2

[0124]

TABLE-US-00003 % by weight active matter E F G H I J K L 2-propanol 5.00 1.25 1.67 5.00 5.00 5.00 5.00 5.00 Ammonia 1.25 0.31 0.42 1.25 1.25 1.25 1.25 1.25 Dyestuff I 0.40 0.10 0.10 0.30 Dyestuff II 0.13 0.10 Dyestuff III 0.40 Dyestuff IV 0.40 Basic Yellow 0.30 87 2-Amino-6- 0.30 chloro-4- nitrophenol Acid Violet 43 0.10 Xanthan Gum 2.00 0.50 Goldwell 25.0 Topchic 6N Goldwell 50.0 33.3 Topchic 6% Lotion Goldwell 33.3 Oxycur Platin Lightening Powder Water to to to to to to to to 100 100 100 100 100 100 100 100