Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1995-07-12
1997-04-01
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
106 22K, 106 20D, 534582, 534605, 534634, 534728, 534797, C09D 1102, C09B 4300
Patent
active
056166940
DESCRIPTION:
BRIEF SUMMARY
The specification describes an invention relating to azo compounds which are useful as the colorants for inks, especially inks used in ink let printing.
According to the present invention there is provided a compound of Formula (1) and salts thereof: ##STR1## Ar.sup.1 and Ar.sup.2 are each independently aryl containing at least two carboxy groups; and ##STR2## in which T.sup.1 and T.sup.2 each independently is C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl; and -alkoxy or C.sub.3-4 -alkenyl provided that T.sup.3 and T.sup.4 are not both H; ##STR3## each Z independently is H, halogen, alkyl, NR.sup.1 R.sup.2, SR.sup.3 or OR.sup.3 ; substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, aryl, substituted aryl, aralkyl, substituted aralkyl or R.sup.1 .sub.and R.sup.2 together with the nitrogen atom to which they are attached form a 5 or 6 membered ring;
It is preferred that the dye of Formula (1) has at least as many carboxy groups as sulpho groups.
Each of the groups Ar.sup.1 and Ar.sup.2 is preferably naphthyl or phenyl, especially phenyl which may carry further substituents in addition to the two carboxy groups. The additional substituents are preferably selected from alkyl, especially C.sub.1-4 -alkyl; alkoxy, especially C.sub.1-4 -alkoxy; --SO.sub.3 H; --PO.sub.3 H.sub.2 ; --COSH; --OH; --CO.sub.2 H; halogen, especially Cl or Br; and optionally substituted C.sub.1-4 -alkyl. However, it is preferred that each of Ar.sup.1 and Ar.sup.2 carries only two carboxy groups, and is more preferably dicarboxyphenyl, such as 2,4-dicarboxyphenyl, 2,3-dicarboxyphenyl, 3,4-dicarboxyphenyl, and especially 3,5-dicarboxyphenyl. It is also preferred that Ar.sup.1 and Ar.sup.2 are identical.
It is preferred that the chromophores Ar.sup.1 N.dbd.N-J- and Ar.sup.2 N.dbd.N-J-are identical or similar so that they absorb light at approximately the same wavelength.
The variable --SO.sub.3 H group in each J, which may be meta- or para- with respect to the NH group, is preferably in the meta-position, so that J is the divalent residue of H-acid.
Examples of the alkyl, alkoxy and alkenyl groups represented by T.sup.1, T.sup.2, T.sup.3 and T.sup.4 in the divalent group L are methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, t-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, t-butoxy and allyl. In the group of Formula (3a), T.sup.1 and T.sup.2 are preferably identical more preferably C.sub.1-4 -alkyl and, especially, each is methyl, so that L is especially 2,5-dimethylphen-1,4-ylene-diamino. In the group of Formula (3b), T.sup.3 is preferably H or C.sub.1-4 -alkyl, especially methyl and T.sup.4 is preferably H or C.sub.1-4 -alkyl, especially methyl (provided T.sup.3 and T.sup.4 are not both H) and L is especially 2,5-dimethylpiperazin-1,4-ylene or 2-(5-)methylpiperazin-1,4-ylene.
When X is of Formula (5) it is preferred that Z is attached to the carbon atom between the two ring nitrogen atoms and that Y is para to Z. Each X is preferably of Formula (4).
Z is preferably Cl, OR.sup.3, SR.sup.3 or NR.sup.1 R.sup.2, especially Cl; OH; SH; alkoxy, such as methoxy or ethoxy; hydroxy-C.sub.2-4 -alkylamino, such as mono or di-(2-hydroxyethyl)amino; morpholinyl; piperidinyl; piperazinyl; 4-(hydroxy-C.sub.2-4 -alkyl)-piperazin-1-yl, such as 4-hydroxyethylpiperazin-1-yl; 4-(C.sub.1-4 -alkyl) piperazin-1-yl, such as 4-methylpiperazin-1-yl; C.sub.1-6 -alkylamino, such as dimethylamino, n-butylamino or n-hexylamino; carboxy-C-.sub.1-4 -alkylamino, such as 2-carboxymethylamino; arylamino, such as phenylamino, mono-3- or di-3,5-carboxyanilino; or aralkylamino, such as benzylamino, mono-3- or di-3,5-carboxyphenylmethylamino. Where Z is alkyl or alkoxy these preferably contain from 1 to 4 carbon atoms. Where at least one Z is halogen, the compound of Formula (1) may be reactive with cellulose under appropriate temperature and pH conditions. However, this does not appear to contribute to the wet-fastness of the compound when applied to a paper substrate under the normal conditions used in ink jet printing and comp
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patent: 3647778 (1972-03-01), Andrew et al.
patent: 4584367 (1986-04-01), Matsuo et al.
patent: 5262527 (1993-11-01), Gregory et al.
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patent: 5473053 (1995-12-01), Kenyon et al.
Kenyon Ronald W.
Mistry Prahalad M.
Powers Fiona T.
Zeneca Limited
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