Triarylmethane dyes
AssigneeCiba Corporation
InventorsChristian Cremer, Olof Wallquist
Life of this patent
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Abstract
Disclosed are triarylmethane dye compounds of formula (2) wherein R8 is C1-C12alkyl, C1-C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or the radical —NR6R7 or —OR8; B1 and B2, independently from each other are C6-C10aryl; or a 5-7-membered heterocyclic compound, which may be substituted by C1-C12alkyl, C1-C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or by the radical —NR6R7 or —OR6; and R6 and R7 independently from each other are hydrogen; or C1-C12alkyl, which may be substituted by hydroxy or C6-C10aryl.
Claims17
Compounds of formula (1)
- D1-(Z1)r—Y1—S-A (1)
- wherein
- A is hydrogen;
- a radical of formula (1b) *—S—Y2—(Z2)r-D2;
- or a radical of formula
- *—S—Y3 (1c)
- Y1 and Y2 independently from each other are unsubstituted or substituted, straight-chain or branched, interrupted or uninterrupted C1-C10alkylene;
- C5-C10cycloalkylene;
- C5-C10arylene;
- or —C5-C10arylene-(C1-C10alkylene);
- Y3 is an unsubstituted or substituted, straight-chain or branched, interrupted or uninterrupted C1-C10alkyl;
- C5-C10cycloalkyl;
- or C5-C10aryl-(C1-C10alkyl);
- Z1 and Z2 independently from each other are *—(CH2)p—C(O)—**;
- *—(CH2CH2—O)s—**;
- *—(CH2)p—C(O)O—**;
- *—(CH2)p—OCO—**;
- *—(CH2)p—N(R1)—**;
- *—(CH2)p—CON(R1)—**;
- *—(CH2)p—(R1)NC(O)—**;
- —O—;
- —S—;
- —S(O)—;
- —S(O)2—;
- or a cationic biradical of a substituted or unsubstituted aromatic or heteroaromatic compound of the formula
- wherein
- the asterix * indicates the linkage to D1 and/or D2;
- the asterix ** indicates the linkage to Y1 and/or Y2;
- W1 is N or a radical of CR5;
- R1, R2, R3, R4 and R5 independently from each other are hydrogen;
- C1-C14alkyl;
- C2-C14alkenyl;
- C5-C10aryl;
- C5-C10aryl-(C1-C10alkyl);
- or —C1-C10alkyl(C5-C10aryl);
- D1 and D2 independently from each other are the residue of an organic dye selected from the radical of formula
- wherein
- B1 and B2, independently from each other are C6-C10aryl;
- or a 5-7-membered heterocyclic compound, which may be substituted by C1-C12alkyl, C1-C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or by the radical —NR6R7 or —OR6;
- B3 is C6-C10arylene, or a bivalent radical of a 5-7-membered heterocyclic compound, which may be substituted by C1-C12alkyl, C1-C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or by the radical —NR6R7 or —OR6;
- R6 and R7 independently from each other are hydrogen;
- or C1-C12alkyl, which may be substituted by hydroxy or C6-C10aryl;
- or
- R6 and R7 together with the linking nitrogen atom form a 5 to 7 membered heterocyclic ring;
- or
- R6 and R7 together with the linking nitrogen atom form a piperidine ring
- An is an anion;
- p is a number from 0 to 5;
- r is 0 or 1;
- and
- s is a number from 1 to 5.
A method of dyeing keratin-containing fibers comprising treating the fiber with at least one compound of formula (1)
- D1-(Z1)r—Y1—S-A (1)
- wherein
- A is hydrogen;
- a radical of formula (1b) *—S—Y2—(Z2)r-D2;
- or a radical of formula
- *—S—Y3 (1c)
- Y1 and Y2 independently from each other are unsubstituted or substituted, straight-chain or branched, interrupted or uninterrupted C1-C10alkylene;
- C6-C10cycloalkylene;
- C6-C10arylene;
- or —C6-C10arylene-(C1-C10alkylene);
- Y3 is an unsubstituted or substituted, straight-chain or branched, interrupted or uninterrupted C1-C10alkyl;
- C6-C10cycloalkyl;
- C6-C10aryl;
- or —C6-C10aryl-(C1-C10alkyl);
- Z1 and Z2 independently from each other are *—(CH2)p—C(O)—**;
- *—(CH2CH2—O)s—**;
- *—(CH2)p—C(O)O—**;
- *—(CH2)p—OCO—**;
- *—(CH2)p—N(R1)—**;
- *—(CH2)p—CON(R1)—**;
- *—(CH2)P—(R1)NC(O)—**;
- —O—;
- —S—;
- —S(O)—;
- —S(O)2—;
- or a cationic biradical of a substituted or unsubstituted aromatic or heteroaromatic compound of the formula
- the asterix * indicates the linkage to D1 and/or D2;
- the asterix ** indicates the linkage to Y1 and/or Y2;
- W1 is N or a radical of CR5;
- R1, R2, R3, R4 and R5 independently from each other are hydrogen;
- C1-C14alkyl;
- C2-C14alkenyl;
- C5-C10aryl;
- C6-C10aryl-(C1-C10alkyl);
- or —C1-C10alkyl(C6-C10aryl);
- D1 and D2 independently from each other are hydrogen;
- or the residue of an organic dye selected from the radical of formula
- wherein
- B1 and B2, independently from each other are C6-C10aryl;
- or a 5-7-membered heterocyclic compound, which may be substituted by C1-C12alkyl, C1-C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or by the radical —NR6R7 or —OR6;
- B3 is C6-C10 arylene, or a bivalent radical of a 5-7-membered heterocyclic compound, which may be substituted by C1-C12alkyl, C1-C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or by the radical —NR6R7 or —OR6;
- R6 and R7 independently from each other are hydrogen;
- or C1-C12alkyl, which may be substituted by hydroxy or C6-C10aryl;
- or
- R6 and R7 together with the linking nitrogen atom form a 5 to 7 membered heterocyclic ring;
- or
- R6 and R7 together with the linking nitrogen atom form a piperidine ring;
- An is an anion;
- p is a number from 0 to 5;
- r is 0 or 1;
- and
- s is a number from 1 to 5.
A composition comprising at least one compound of formula (1)
- D1-(Z1)r—Y1—S-A (1)
- wherein
- A is hydrogen;
- a radical of formula (1b) *—S—Y2—(Z2)r-D2;
- or a radical of formula
- *—S—Y3 (1c)
- Y1 and Y2 independently from each other are unsubstituted or substituted, straight-chain or branched, interrupted or uninterrupted C1-C10alkylene;
- C5-C10cycloalkylene;
- C5-C10arylene;
- or C5-C10arylene-(C1-C10alkylene);
- Y3 is an unsubstituted or substituted, straight-chain or branched, interrupted or uninterrupted C1-C10alkyl;
- C5-C10cycloalkyl;
- or —C5-C10aryl-(C1-C10alkyl);
- Z1 and Z2 independently from each other are *—(CH2)p—C(O)—**;
- *—(CH2CH2—O)s—**;
- *—(CH2)p—C(O)O—**;
- *—(CH2)p—OCO—**;
- *—(CH2)p—N(R1)—**;
- *—(CH2)p—CON(R1)—**;
- *—(CH2)p—(R1)NC(O)—**;
- —O—;
- —S—;
- —S(O)—;
- —S(O)2—;
- or a cationic biradical of a substituted or unsubstituted aromatic or heteroaromatic compound of the formula
- wherein
- the asterix indicates the linkage to D1 and/or D2;
- the asterix ** indicates the linkage to Y1 and/or Y2;
- W1 is N or a radical of CR5;
- R1, R2, R3, R4 and R5 independently from each other are hydrogen;
- C1-C14alkyl;
- C2-C14alkenyl;
- C5-C10aryl;
- C5-C10aryl-(C1-C10alkyl);
- or —C1-C10alkyl(C5-C10aryl);
- D1 and D2 independently from each other are the residue of an organic dye selected from the radical of formula
- wherein
- B1 and B2, independently from each other are C6-C10aryl;
- or a 5-7-membered heterocyclic compound, which may be substituted by C1-C12alkyl, C1-C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or by the radical —NR6R7 or —OR6;
- B3 is C6-C10arylene, or a bivalent radical of a 5-7-membered heterocyclic compound, which may be substituted by C1-C12alkyl, C1-C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or by the radical —NR6R7 or —OR6;
- R6 and R7 independently from each other are hydrogen;
- or C1-C12alkyl, which may be substituted by hydroxy or C6-C10aryl;
- or
- R6 and R7 together with the linking nitrogen atom form a 5 to 7 membered heterocyclic ring;
- or
- R6 and R7 together with the linking nitrogen atom form a piperidine ring;
- An is an anion;
- p is a number from 0 to 5;
- r is 0 or 1;
- and
- s is a number from 1 to 5.
Dependencies are inferred from the claim text.