Gas-resistant phtalocyanine dyes
The present invention relates to dyes of formula (1), wherein Pc is a phthalocyanine of formula (2), Me is a metal, [MePc] is a phthalocyanine-metal complex of formula (3), M + is an inorganic or organic cation, R 1 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted aralkyl or unsubstituted or substituted aryl, and R 2 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted aralkyl or unsubstituted or substituted aryl, and n and m are each independently of the other 0, 1, 2, 3, 4, 5, 6, 7 or 8, the sum of (n+m) being a number 5, 6, 7 or 8, and also to mixtures thereof, to processes for the preparation thereof and to the use thereof in dyeing or printing natural, semi-synthetic or synthetic material.
1. A dye having the formula
wherein
R 1 is hydrogen;
R 2 is hydrogen, unsubstituted C 1-12 alkyl or C 1-12 alkyl substituted by SO 3 H; and
n and m are each independently 0, 1, 2, 3, 4, 5, 6 or 7, the sum of (n+m) being 7.
2. A process for preparing a dye according to claim 1 , said process comprising:
sulfonating a compound of formula
using a strong sulfonating agent;
optionally neutralising the resulting sulfonic acid using a compound containing H + ; and
optionally converting the sulfonic acid, or its salt into a sulfochloride and reacting the sulfochloride with ammonia or an amine.
3. A dye mixture comprising at least one dye (1) according to claim 1 and at least one other dye.
4. The dye mixture of claim 3 , wherein the at least one other dye is a dye of formula (I)
at least one dye of formula (1) wherein n and m are each independently number from 0 to 4 such that the sum of (m+n) is from 1 to 4
wherein
Pc is a phthalocyanine of formula
Me is a metal;
[MePc] is a phthalocyanine-metal complex of formula
M + is an inorganic or organic cation;
R 1 is hydrogen; and
R 2 is hydrogen, unsubstituted C 1-12 alkyl, or C 1-12 alkyl substituted by SO 3 H.
5. The dye mixture according to claim 3 , said mixture comprising from 5 to 99% by weight of the at least one dye according to claim 1 .
6. A method of dyeing or printing natural, semi-synthetic, or synthetic material, said method comprising applying one or more dyes according to claim 1 to said natural, semi-synthetic, or synthetic material.
7. An ink containing from 1 to 35% by weight of at least one dye of formula (1) according to claim 1 .
8. A method of printing a natural, semi-synthetic, or synthetic material using an inkjet printing method, said method of printing comprising applying in which method an ink according to claim 7 to said natural, semi-synthetic, or synthetic material.
9. The method according to claim 8 , wherein natural, semi-synthetic, or synthetic material is paper, a plastics film, or a textile fiber material.
10. The method according to claim 9 , wherein paper is a microporous photo paper.
11. A natural, semi-synthetic, or synthetic material dyed with or printed onto with a dye according to claim 1 .
12. The process according to claim 2 , wherein the strong sulfonating agent is chlorosulfonic acid or oleum/sulfuric acid monohydrate.
13. The dye mixture according to claim 5 , said mixture comprising from 10 to 99% by weight of the at least one dye according to claim 1 .
14. The method of dyeing or printing natural, semi-synthetic, or synthetic material according to claim 6 , wherein the natural, semi-synthetic, or synthetic material is a textile material.
15. The method according to claim 9 , wherein the paper is photo paper.
16. A dye of formula
wherein R is OH or NH 2 ,
or a dye of formula
17. The method of claim 2 , wherein converting the sulfonic acid, or its salt, into a sulfochloride comprises reacting the sulfonic acid, or its salt, with thionyl chloride or phosphorus oxychloride.