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US 7,731,760 B2Granted
Oxazine disulfide dyes
AssigneeCiba Corporation
InventorsChristian Cremer, Olof Wallquist
Life of this patent
Estimating the term…
Abstract
Disclosed are certain oxazine disulfide dyes useful for the dyeing of organic materials, such as keratin fibers, preferably human hair. the dyes are for instance of the formulae
Claims14
Compounds of formula (1)
- D1-(Z1)r—Y1—S-A (1),
- wherein
- A is hydrogen;
- or a radical of formula (1a) *—S—Y2—(Z2)r-D2;
- 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);
- 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 ar the residue of an organic dye selected from the radical of formula
- R6 and R7 independently from each other are hydrogen;
- C1-C20alkyl;
- C1-C20alkoxy;
- C3-C6cycloalkyl;
- C5-C10aryl;
- anellated aromatic groups;
- carboxylate;
- or sulfonate groups;
- R8, R9 and R10, R11 and R12 each independently from each other are hydrogen;
- unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted C1-C14alkyl, C2-C14alkenyl, C6-C10aryl, C6-C10aryl-C1-C10alkyl or C5-C10alkyl(C5-C10aryl);
- or
- R8 and R9 or R10 and R11 together with the linking nitrogen atom form a 5 to 7 membered carbocyclic ring which may contain one or more than one hetero atom;
- or
- R8 is linked to C1 together with N+ forming a 5-7 membered carbocyclic ring;
- or
- R9 is linked to C2 together with N+ forming a 5-7 membered carbocyclic ring;
- X is —O—;
- or —N(R9)—;
- or —S—;
- p is a number from 0 to 5;
- r is 0 or 1;
- and
- s is a number from 1 to 5.
51 more elements
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;
- or a radical of formula (1a) *—S—Y2—(Z2)r-D2;
- 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);
- 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 ar the residue of an organic dye selected from the radical of formula
- R6 and R7 independently from each other are hydrogen;
- C1-C20alkyl;
- C1-C20alkoxy;
- C3-C6cycloalkyl;
- C5-C10aryl;
- anellated aromatic groups;
- carboxylate;
- or sulfonate groups;
- R8, R9 and R10, R11 and R12, each independently from each other are hydrogen;
- unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted C1-C14alkyl, C2-C14alkenyl, C6-C10aryl, C6-C10aryl-C1-C10alkyl or C5-C10alkyl(C5-C10aryl);
- or
- R8 and R9 or R10 and R11 together with the linking nitrogen atom form a 5 to 7 membered carbocyclic ring which may contain one or more than one hetero atom;
- or
- R8 is linked to C1 together with N+ forming a 5-7 membered carbocyclic ring;
- or
- R9 is linked to C2 together with N+ forming a 5-7 membered carbocyclic ring;
- X is —O—;
- or —N(R9)—;
- or —S—;
- p is a number from 0 to 5;
- r is 0 or 1;
- and
- s is a number from 1 to 5.
51 more elements
A composition comprising at least one compound of formula (1)
- D1-(Z1)r—Y1—S-A (1),
- wherein
- A is hydrogen;
- or a radical of formula (1a) *—S—Y2—(Z2)r-D2;
- 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);
- 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 ar the residue of an organic dye selected from the radical of formula (1f)
- R6 and R7 independently from each other are hydrogen;
- C1-C20alkyl;
- C1-C20alkoxy;
- C3-C6cycloalkyl;
- C5-C10aryl;
- anellated aromatic groups;
- carboxylate;
- or sulfonate groups;
- R8, R9 and R10, R11 and R12 each independently from each other are hydrogen;
- unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted C1-C14alkyl, C2-C14alkenyl, C6-C10aryl, C6-C10aryl-C1-C10alkyl or C5-C10alkyl(C5-C10aryl);
- or
- R8 and R9 or R10 and R11 together with the linking nitrogen atom form a 5 to 7 membered carbocyclic ring which may contain one or more than one hetero atom;
- or
- R8 is linked to C1 together with N+ forming a 5-7 membered carbocyclic ring;
- or
- R9 is linked to C2 together with N+ forming a 5-7 membered carbocyclic ring;
- X is —O—;
- or —N(R9)—;
- or —S—;
- p is a number from 0 to 5;
- r is 0 or 1;
- and
- s is a number from 1 to 5.
51 more elements
Dependencies are inferred from the claim text.