Cationic imidazolazo dyes containing a 2,5-diaminophenyl moiety

• US 7,482,438 B2
• Filed: 03/23/2005
• Issued: 01/27/2009
• Est. Priority Date: 04/02/2004
• Status: Expired due to Fees

• Current Assignee: CIBA Specialty Chemicals
• Original Assignee: CIBA Specialty Chemicals
• Inventors: Fröhling, Beate, Sauder, Thomas, Kauffmann, Dominique, Eliu, Victor Paul
• Primary Examiner(s): Sample; David R
• Assistant Examiner(s): HAMMER, KATIE L
• Application Number:
  US10/594,047
• Publication Number:
  US 20070214580A1
• Time in Patent Office: 1,406 Days
• Field of Search: 534/560, 534/574, 548/333, 252/187.23, 840/5, 842/5
• US Class Current: 534/558
• CPC Class Codes: C09B 44/16 1,3-Diazoles or hydrogenated 1,3-diazoles ; (Benz)imidazolium

Abstract

Disclosed are azo dyes of formula (1), wherein R₁ is hydrogen; C₁-C₁₄alkyl; hydroxy-C₁-C₁₄alkyl; C₂-C₁₄alkenyl; a radical of formula (1a) —(CH₂)_n1—O—(CH₂)_n2—CH₃; a radical of formula (1b) C₁₀aryl; or C₆-C₁₀aryl-C₁-C₆alkyl; R3 is hydrogen; C₁-C₁₄alkyl; C₂-C₁₄alkenyl; C₆-C₁₀aryl; C₆-C₁₀aryl-C₁-C₆alkyl; or CO—R₆; R₄ is CO—R₆; R₅ is C₁-C₁₄alkyl; C₂-C₁₄alkenyl; C₆-C₁₀aryl; or C₆-C₁₀aryl-C₁-C₆alkyl; R₆ is hydrogen; C₁-C₁₄alkyl; C₂-C₁₄alkenyl; or C₆-C₁₀aryl; R₇, R₈, R₉ and R₁₀, independently from each other are hydrogen; or C₁-C₅alkyl; m is 1; or 2; An⁻ is an anion; If m=1, R₂ is hydrogen; C₁-C₁₄alkyl; C₂-C₁₄alkenyl; a radical of formula (1a); a radical of formula (1b); C₆-C₁₀aryl; or C₆-C₁₀aryl-C₁-C₆alkyl; If m=2, R₂ is the direct bond; or C₁-C₁₄alkylene, which is optionally substituted by one or more C₁-C₄alkyl, or which is optionally interrupted by C₅-C₁₀arylene, —O— or —NR₉R₁₀—; R₉ and R₁₀, independently from each other are hydrogen; or C₁-C₅alkyl; and n1, n2, n3 and n4, independently from each other are a number from 0 to 5. The compounds are useful for the dyeing of organic material, preferably human hair.

Claims

1. Dye of formula

2. Dye according to claim 1, wherein

the anion is is selected from a halide, sulfate, hydrogen sulfate, phosphate, boron tetrafluoride, carbonate, bicarbonate, oxalate or C₁-C₈alkyl sulfate, lactate, formate, acetate, propionate and a complex anion.

3. Dye according to claim 1, wherein

R₁ is hydrogen;

or C₁-C₁₄alkyl;

R₃ is hydrogen;

or C₁-C₁₄alkyl;

R₄ is CO—

R₆;

R₅ is C₁-C₁₄alkyl;

R₆ is hydrogen;

C₁-C₁₄alkyl;

or C₆-C₁₀aryl;

m is 1;

or 2;

An⁻

is an anion;

If m=1,

R₂ is hydrogen;

C₁-C₁₄alkyl;

hydroxy-C₁-C₁₄alkyl a radical of formula (1a);

or a radical of formula (1b);

if m=2,

R₂ is the direct bond;

or C₁-C₁₂alkylene, which is optionally substituted by one or more C₁-C₄alkyl or interrupted by —

O—

, or NR₉R₁₀; and

R₉ and R₁₀ independently from each other are hydrogen;

or C₁-C₅alkyl.

4. Dye according to claim 1, which correspond to formula

5. Dye according to claim 4, wherein

R₁ is hydrogen;

or C₁-C₄alkyl;

R₂ is C₁-C₁₄alkyl;

a radical of formula (1a);

or a radical of formula (1b);

An⁻

is an anion;

R₃ is hydrogen;

or C₁-C₄alkyl;

R₄ is CO—

R₆;

R₅ and R₆ independently from each other are is C₁-C₄alkyl.

6. Dye according to claim 4, wherein

R₁ is hydrogen;

or C₁-C₄alkyl;

R₂ is C₁-C₁₂alkyl;

a radical of formula (1a);

or a radical of formula (1b);

An⁻

is an anion;

R₃ is hydrogen;

C₁-C₄alkyl;

o

R₄ is CO—

CH₃; and

R₅ is C₁-C₄alkyl.

7. Dye according to claim 1 which correspond to formula

8. Dye according to claim 7, wherein

R₁ is hydrogen;

or C₁-C₄alkyl;

R₂ is the direct bond;

or C₁-C₈-alkylene, which is optionally substituted by one or more C₁-C₄alkyl or interrupted by —

O—

, or NR₉R₁₀;

R₃ is hydrogen;

or C₁-C₄alkyl;

R₄ is CO—

R₆;

R₅ is C₁-C₄alkyl;

R₆ is C₁-C₄alkyl;

R₉ and R₁₀ independently from each other are hydrogen;

or C₁-C₅alkyl; and

An⁻

is an anion.

9. Dye according to claim 7, wherein

R₁ is hydrogen;

or C₁-C₄alkyl;

R₂ is is the direct bond;

or C₁-C₈-alkylene, which is optionally substituted by one or more C₁-C₄alkyl or interrupted by —

O—

, or NR₉R₁₀;

R₃ is hydrogen;

or C₁-C₄alkyl;

R₄ is CO—

CH₃;

R₅ is C₁-C₄alkyl;

R₉ and R₁₀ independently from each other are hydrogen;

or C₁-C₅alkyl; and

An⁻

is an anion.

10. Dye according to claim 1 of formula

12. A process for the preparation of dyes of formula (1) as defined in claim 1, which process comprises reacting a dye of formula (17) with an amine of formula (18) to give a compound of formula (1) according to the following reaction scheme:

14. A composition comprising at least one dye of formula (1) as defined in claim 1.

15. A composition according to claim 14 comprising in addition at least one single further direct dye and/or an oxidative agent.

16. A composition according to claim 14 comprising in addition at least one single oxidative dye and/or;

at least one single oxidative dye and an oxidative agent.

17. A composition according to claim 14 in the form of a shampoo, a conditioner, a gel or an emulsion.

18. A method of dyeing an organic material, which comprises treating the organic material with at least one dye of formula (1) according to claim 1.

19. A method according to claim 18, which comprises treating the organic material with at least one dye of formula (1) and an oxidative agent and, optionally, a further direct dye.

20. A method according to claim 18, which comprises treating the organic material with at least one compound of formula (1) and at least one single oxidative dye, or treating the organic material with a dye of formula (1) and at least one single oxidative dye and an oxidative agent.

21. A method according to any of claim 18 wherein the organic material is selected from keratin-containing fibers.

22. A method according to claim 21 wherein the keratin-containing fiber is human hair.

11. A dye of formula

13. Process for the preparation of dye of formula (17)