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US 7,794,509 B2Granted
Tricationic dyes
AssigneeCiba Corporation
InventorsChristian Cremer, Olof Wallquist, Victor Paul Eliu, Kishor Ramachandra Nivalkar
Life of this patent
Estimating the term…
Abstract
Disclosed are tricationic dye compounds, useful for dyeing hair, wool, leather, silk, cellulose or polyamides. The dye compounds are of formula (1), where the groups are as defined in the specification and claims. [D-E1=E2-K]3+(An1−) (An2−) (An3−) (1)
Claims26
Compounds of formula
- D is an aromatic or a cationic heteroaromatic group, which is optionally substituted by one or more than one C1-C14alkyl, C1-C14alkoxy, hydroxy-C1-C14alkyl, C3-C8cycloalkyl, —CN, NO2, —NR3R4, halogen, C6-C10aryl, which is optionally substituted or C1-C14alkyl, or by one or more groups Z;
- E1 and E2 independently from each other are ═CH;
- or ═N—;
- K is an aromatic or heteroaromatic group which is optionally substituted by one or more than one C1-C14alkyl, C1-C14alkoxy, C3-C8cycloalkyl, C6-C10aryl, halogen, hydroxy, NO2, —NR3R4, —N(R3)(CO)R4, —SO2NR3R4, —SONR3R4 or by one or more Z;
- or a radical of formula —NR1R2;
- R1 and R2 independently from each other are hydrogen;
- C1-C14alkyl;
- cyclo-C1-C14alkyl;
- C6-C10aryl;
- an aromatic or heteroaromatic group which is optionally substituted by one or more than one C1-C14alkyl, C1-C14alkoxy, C3-C8cycloalkyl, C6-C10aryl, halogen, hydroxy, —NR5R6, —N(R5)—(CO)R5 or by Z;
- Z is a group of the formula (1a) *—X1—Y1—W1, wherein
- X1 is the direct bond;
- —NR7—;
- —O—;
- —NR7(C═O)—;
- —(CO)NR7—;
- —O(C═O)—;
- —(CO)O—;
- or —(C═O)—;
- Y1 is the direct bond;
- C1-C12alkylene, which is optionally interrupted by —O—, —NR8, —S—, —(C═O)—, —O(C═O)—, (C═O)O—, —NR7(C═O)—, —(C═O)NR7—, and which may substituted by C1-C14alkyl, hydroxy-C1-C14alkyl, hydroxy, —NR9R10 or halogen;
- or C6-C10arylene, which may substituted by C1-C 14alkyl, hydroxy-C1-C14alkyl, hydroxy, amino or halogen;
- W1 is a cationic group;
- and
- R3, R4, R5, R6, R7, R8, R9 and R10 independently from each other are hydrogen;
- C1-C14alkyl;
- or Z;
- and
- An1−, An2− and An3− independently from each other are an anion with the proviso that 2 radicals represent Z in order to obtain an overall charge of 3+.
26 more elements
A method of dyeing organic material, which comprises treating the organic material with at least one dye of formula (1)
- D is an aromatic or a cationic heteroaromatic group, which is optionally substituted by one or more than one C1-C14alkyl, C1-C14alkoxy, hydroxy-C1-C14alkyl, C3-C8cycloalkyl, —CN, NO2, —NR3R4, halogen, C6-C10aryl, which is optionally substituted or C1-C14alkyl, or by one or more groups Z;
- E1 and E2 independently from each other are ═CH;
- or ═N—;
- K is an aromatic or heteroaromatic group which is optionally substituted by one or more than one C1-C14alkyl, C1-C14alkoxy, C3-C8cycloalkyl, C6-C10aryl, halogen, hydroxy, NO2, —NR3R4, —N(R3)(CO)R4, —SO2NR3R4, —SONR3R4 or by one or more Z;
- or a radical of formula —NR1R2;
- R1 and R2 independently from each other are hydrogen;
- C1-C14alkyl;
- cyclo-C1-C14alkyl;
- C6-C10aryl;
- an aromatic or heteroaromatic group which is optionally substituted by one or more than one C1-C14alkyl, C1-C14alkoxy, C1-3—C8cycloalkyl, C6-C10aryl, halogen, hydroxy, —NR5R6, —NR5(R5)—(CO)R5 or by Z;
- Z is a group of the formula (1a) *—X1—Y1—W1, wherein
- X1 is the direct bond;
- —NR7—;
- —O—;
- —NR7(C═O)—;
- —(CO)NR7—;
- —O(C═O)—;
- —(CO)O—;
- or —(C═O)—;
- Y1 is the direct bond;
- C1-C12alkylene, which is optionally interrupted by —O—, —NR8, —S—, —(C═O)—, —O(C═O)—, (C═O)O—, —NR7(C═O)—, —(C═O)NR7—, and which may substituted by C1-C14alkyl, hydroxy-C1-C14alkyl, hydroxy, —NR9R10 or halogen;
- or C6-C10arylene, which may substituted by C1-C14alkyl, hydroxy-C1-C14alkyl, hydroxy, amino or halogen;
- W1 is a cationic group;
- and
- R3, R4, R5, R6, R7, R8, R9 and R10 independently from each other are hydrogen;
- C1-C14alkyl;
- or Z;
- and
- An1−1, An2− and An3− independently from each other are an anion with the proviso that 2 radicals represent Z in order to obtain an overall charge of 3+.
26 more elements
A method of dyeing organic material, which comprises treating the organic material with a composition comprising at least one dye of formula (1)
- D is an aromatic or a cationic heteroaromatic group, which is optionally substituted by one or more than one C1-C14alkyl, C1-C14alkoxy, hydroxy-C1-C14alkyl, C3-C8cycloalkyl, —CN, NO2, —NR3R4, halogen, C6-C10aryl, which is optionally substituted or C1-C14alkyl, or by one or more groups Z;
- E1 and E2 independently from each other are ═CH;
- or ═N—;
- K is an aromatic or heteroaromatic group which is optionally substituted by one or more than one C1-C14alkyl, C1-C14alkoxy, C3-C8cycloalkyl, C6-C10aryl, halogen, hydroxy, NO2, —NR3R4, —N(R3)(CO)R4, —SO2NR3R4, —SONR3R4 or by one or more Z;
- or a radical of formula —NR1R2;
- R1 and R2 independently from each other are hydrogen;
- C1-C14alkyl;
- cyclo-C1-C14alkyl;
- C6-C10aryl;
- an aromatic or heteroaromatic group which is optionally substituted by one or more than one C1-C14alkyl, C1-C14alkoxy, C3-C8cycloalkyl, C6-C10aryl, halogen, hydroxy, —NR5R6, —N(R5)—(CO)R5 or by Z;
- Z is a group of the formula (1a) *—X1—Y1—W1, wherein
- X1 is the direct bond;
- —NR7—;
- —O—;
- —NR7(C═O)—;
- —(CO)NR7—;
- —O(C═O)—;
- —(CO)O—;
- or —(C═O)—;
- Y1 is the direct bond;
- C1-C12alkylene, which is optionally interrupted by —O—, —NR8, —S—, —(C═O)—, —O(C═O)—, (C═O)O—, —NR7(C═O)—, —(C═O)NR7—, and which may substituted by C1-C14alkyl, hydroxy-C1-C14alkyl, hydroxy, —NR9R10 or halogen;
- or C6-C10arylene, which may substituted by C1-C14alkyl, hydroxy-C1-C14alkyl, hydroxy, amino or halogen;
- W1 is a cationic group;
- and
- R3, R4, R5, R6, R7, R8, R9 and R10 independently from each other are hydrogen;
- C1-C14alkyl;
- or Z;
- and
- An1−, An2− and An3− independently from each other are an anion with the proviso that 2 radicals represent Z in order to obtain an overall charge of 3+.
26 more elements
Dependencies are inferred from the claim text.