Azo compound
AssigneeZeneca Limited
InventorsRonald W. Kenyon, Prahalad M. Mistry
Life of this patent
Estimating the term…
Abstract
A compound of Formula (1) and salts thereof wherein the variables are as defined in the specification: Ar.sup.1 N.dbd.N-J-X-L-X-J-N.dbd.NAr.sup.2 (1) A compound of Formula (1) is suitable for use in the coloration of cellulosic substrates, such as paper, to give bright prints with good light and water fastness. It is especially suitable for use in the printing of paper by non-impact printing techniques, such as ink jet printing, especially thermal ink jet printing.
Claims18
In a process for ink jet printing a substrate with an ink, the improvement wherein the ink contains a compound selected from the group consisting of a compound of Formula (1) and salts thereof:
- Ar.sup.1 N.dbd.N-J-X-L-X-J-N.dbd.NAr.sub.2 ( 1)
- wherein:
- J is ##STR9## Ar.sup.1 and Ar.sup.2 are each independently aryl containing at least two carboxy groups;
- and
- L is a group of the Formula (3b):
- ##STR10## in which T.sup.3 and T.sup.4 each independently is H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl provided that T.sup.3 and T.sup.4 are not both H;
- each X independently is a group of the Formula (4), (5) or (6):
- ##STR11## each Z independently is H, halogen, alkyl, NR.sup.1 R.sup.2, SR.sup.3 or OR.sup.3 ;
- each Y independently iS Z, SR.sup.4 or OR.sup.4 ;
- each E independently is Cl or CN;
- and
- R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, aryl, substituted aryl, aralkyl or substituted aralkyl,
- or R.sup.1 and R.sup.2, together with the nitrogen atom to which they are attached, form a 5 or 6 membered ring.
A process for the preparation of a compound of Formula (1)
- Ar.sup.1 N.dbd.N-J-X-L-X-J-N.dbd.NAr.sub.2 ( 1)
- wherein:
- J is ##STR12## Ar.sup.1 and Ar.sup.2 are each independently aryl containing at least two carboxy groups;
- and
- L is a group of the Formula (3b):
- ##STR13## in which T.sup.3 and T.sup.4 each independently is H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl provided that T.sup.3 and T.sup.4 are not both H;
- each X independently is a group of the Formula (4), (5) or (6):
- ##STR14## each Z independently is H, halogen, alkyl, NR.sup.1 R.sup.2, SR.sup.3 or OR.sup.3 ;
- each Y independently is Z, SR.sup.4 or OR.sup.4 ;
- each E independently is Cl or CN;
- and
- R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, aryl, substituted aryl, aralkyl or substituted aralkyl, or R.sup.1 and R.sup.2, together with the nitrogen atom to which they are attached, form a 5 or 6 membered ring comprising
- (i) diazotisation of amines Ar.sup.1 NH.sub.2 and Ar.sup.2 NH.sub.2 with a diazotising agent in the cold to give the corresponding diazonium salts;
- (ii) condensation of HJH with a compound halo-X-halo, to give a compound, HJ-X-halo, in which X is as defined above except that Z is Cl;
- (iii) coupling each of the diazonium salts from (i) above with an equivalent of a compound, HJ-X-halo to give compounds, Ar.sup.1 N.dbd.N-J-X-halo and Ar.sup.2 N.dbd.N-J-X-halo, in which each X is the same or different to each other and in which each X is as defined above except that Z is Cl;
- (iv) the products from (iii) are each condensed with a diamine, H-L-H;
- (v) optionally condensing the product from (iv) with a compound, ZH,
- wherein Ar.sup.1, Ar.sup.2, J, X, L and Z are as defined above unless otherise stated.
Dependencies are inferred from the claim text.