Compositions and inks containing disazo dyes
View Patent ↗A process for printing an image on a substrate including applying thereto a composition including a liquid medium and a compound of Formula (1) A-N═N-L-N═N-A wherein: each A independently is optionally substituted aryl or heteroaryl; and L is an optionally substituted, optionally metallised 1,8-dihydroxynaphthylene group; provided that: (i) at most one of the groups represented by A has a hydroxy substituent ortho to the —N═N— groups shown in Formula (1); and (ii) Formula (1) is not: Also claimed are compositions for printing, compounds and processes for making the compounds.
1. A process for printing an image on a substrate comprising applying thereto by means of an ink jet printer a composition comprising a liquid medium and a disazo compound of Formula (1):
A-N═N-L-N═N-A Formula (1)
wherein:
each A independently is aryl or heteroaryl; and
L is an optionally metallised 1,8-dihydroxynaphthylene group;
provided that:
(i) at most one of the groups represented by A has a hydroxy substituent ortho to the —N═N— groups shown in Formula (1); and
(ii) the compound of Formula (1) is not:
2. A process according to claim 1 wherein at least one of the groups represented by A carries a group selected from sulpho and carboxy.
3. A process according to claim 1 wherein A independently is unsubstituted aryl or heteroaryl or aryl or heteroaryl substituted with a member of the group consisting of OH, SO 3 H, PO 3 H 2 , CO 2 H, NO 2 , NH 2 , unsubstituted C 1-4 -alkyl, C 1-4 -alkyl carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, amino or hydroxy group, unsubstituted C 1-4 -alkoxy or C 1-4 -alkoxy carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, C 1-4 -alkyl, amino or hydroxy group, amine, amine carrying one or two unsubstituted C 1-4 -alkyl groups or C 1-4 -alkyl groups substituted with a sulpho, carboxy, phosphato, C 1-4 -alkoxy, amino or hydroxy group, acylamine and ureido.
4. A process according to claim 3 wherein L is a 1,8-dihydroxy-naphthalene group of the Formula (2) or a metal complex thereof:
where a is 1 or 2 and SO 3 H is in the free acid or salt form.
5. The process of claim 1 wherein A is selected from the group consisting of 2-sulphophenyl, 3-sulphophenyl, 4-sulphophenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-sulpho-4-phosphatophenyl, 2-sulpho-4-aminophenyl, 2-sulpho-4-acetylaminophenyl, 2-sulpho-4-methoxyphenyl, 2-sulpho-5-aminophenyl, 3-sulpho-4-nitrophenyl, 3-sulpho-4-aminophenyl, 2-sulpho-4-nitrophenyl, 2,5-disulfophenyl, 2-5-disulpho-4-acetylaminophenyl, 2-hydroxy-3,5-disulphophenyl, 2-carboxy-4-acetylaminophenyl, 2-carboxy-4-aminophenyl, 3,5-dicarboxyphenyl and 2,5-dihydroxyethyloxyphenyl and L is
where a is 2 and the SO 3 H groups shown in Formula (2) are in the 3- and 6-positions or the 3- and 5-positions.
6. A composition for ink jet printing comprising:
(a) 0.2 to 12 parts of a disazo compound of Formula (1):
A-N═N-L-N═N-A Formula (1)
wherein:
each A independently is aryl or heteroaryl and each A is different; and
L is an optionally metallised 1,8-dihydroxynaphthylene group;
provided that at most one of the groups represented by A has a hydroxy substituent ortho to the —N═N— groups shown in Formula (1) and provided that the compound of Formula (1) does not contain any groups of the formula —SO 2 —CH 2 —CH 2 —O—SO 3 H or —SO 2 —CH═CH 2 ; and
(b) from 88 to 99.8 parts of a liquid medium;
wherein all parts are by weight and the number of parts of (a)+(b)=100.
7. A paper, an overhead projector slide or a textile material printed, with a composition as defined in claim 6 .
8. An ink jet printer cartridge, optionally refillable, comprising one or more chambers and a composition, wherein the composition is present in at least one of the chambers and the composition is as defined in claim 6 .
9. A composition according to claim 6 wherein A independently is unsubstituted aryl or heteroaryl or aryl or heteroaryl substituted with a member of the group consisting of OH, SO 3 H, PO 3 H 2 , CO 2 H, NO 2 , NH 2 , unsubstituted C 1-4 -alkyl, C 1-4 -alkyl carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, amino or hydroxy group, unsubstituted C 1-4 -alkoxy or C 1-4 -alkoxy carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, C 1-4 -alkyl, amino or hydroxy group, amine, amine carrying one or two unsubstituted C 1-4 -alkyl groups or C 1-4 -alkyl groups substituted with a sulpho, carboxy, phosphato, C 1-4 -alkoxy, amino or hydroxy group, acylamine and ureido.
10. A composition according to claim 9 wherein L is a 1,8-dihydroxy-naphthalene group of the Formula (2) or a metal complex thereof:
where a is 1 or 2 and SO 3 H is in the free acid or salt form.
11. The composition of claim 6 wherein A is selected from the group consisting of 2-sulphophenyl, 3-sulphophenyl, 4-sulphophenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-sulpho-4-phosphatophenyl, 2-sulpho-4-aminophenyl, 2-sulpho-4-acetylaminophenyl, 2-sulpho-4-methoxyphenyl, 2-sulpho-5-aminophenyl, 3-sulpho-4-nitrophenyl, 3-sulpho-4-aminophenyl, 2-sulpho-4-nitrophenyl, 2,5-disulfophenyl, 2-5-disulpho-4-acetylaminophenyl, 2-hydroxy-3,5-disulphophenyl, 2-carboxy-4-acetylaminophenyl, 2-carboxy-4-aminophenyl, 3,5-dicarboxyphenyl and 2,5-dihydroxyethyloxyphenyl and L is
where a is 2 and the SO 3 H groups shown in Formula (2) are in the 3- and 6-positions or the 3- and 5-positions.
12. A disazo compound of Formula (1):
A-N═N-L-N═N-A Formula (1)
wherein:
each A independently is aryl and each A is different; and
L is an optionally metallised 1,8-dihydroxynaphthylene group;
provided that:
(i) at most one of the groups represented by A has a hydroxy substituent ortho to the —N═N— groups shown in Formula (1); and
(ii) at least one of the groups represented by A carries a group selected from sulpho and carboxy; and
(iii) the compound of formula (1) does not contain any groups of the formula —SO 2 —CH 2 —CH 2 —O—SO 3 H or —SO 2 —CH═CH 2 .
13. A compound of Formula (1) as defined in claim 12 wherein both groups represented by A carry a group selected from sulpho and carboxy.
14. A compound of Formula (1) as defined in claim 13 wherein both groups represented by A carry a sulpho group.
15. A compound of Formula (1) as defined in claim 12 wherein L is of Formula (2)
wherein a is 1 or 2 and SO 3 H is in free acid or salt form.
16. A process for preparing a compound of Formula (1), as defined in claim 12 , which comprises diazotising an amine of formula A-NH 2 to give a diazonium salt, and coupling the resultant diazonium salt with a compound of Formula (6):
A-N═N-LH Formula (6)
wherein L and each A independently are as defined in claim 12 .
17. A process for the preparation of a compound of Formula (1) as defined in claim 12 which comprises reacting a compound of formula A-N═N-Q-N═N-A with a strong base, wherein each A independently is as defined in claim 12 and Q is 6-hydroxy-8-amino-naphthylene group.
18. A process for preparing a compound of Formula (1):
A-N═N-L-N═N-A
wherein
each A independently is aryl or heteroaryl and each A is different; and
L is an optionally metallised 1,8-dihydroxynaphthylene group;
provided that:
(i) at most one of the groups represented by A has a hydroxy substituent ortho to the —N═N— groups shown in Formula (1);
(ii) the compound of Formula (1) is not:
(iii) at least one of the groups represented by A carries a group selected from sulpho and carboxy
(iv) the compound of formula (1) does not contain any groups of the formula —SO 2 —CH 2 —CH 2 —O—SO 3 H or —SO 2 —CH═CH 2 ; and
(v) the compound of Formula (1) is not either of the following structures:
which comprises diazolitising an amine of formula A-NH 2 to give a diazonium salt, and coupling the resultant diazonium salt with a compound of Formula (6):
A-N═N-LH Formula (6).