Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-01-08
1999-02-09
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534797, 8527, 8607, 8620, 8614, 8616, C09B 6724, C09B 6726, C09B 3108
Patent
active
058696270
DESCRIPTION:
BRIEF SUMMARY
This application is A371 of PCT/ GB96/01561 filed Jun. 28, 1996 which designated U.S.
This invention relates to a bis-azo dye composition containing a stabilising agent to protect the dye against decomposition.
It has been found that certain bis-azo dyes, especially such dyes containing carboxy and/or piperazino groups, are useful as colorants of inks for ink jet printing onto paper substrates because they combine good solubility in an aqueous ink medium with good water-fastness on the paper substrate. However, it has also been found that such dyes are susceptible to decomposition, especially when they are stored at an elevated temperature (e.g. above 50.degree. C.) in a de-aerated solution in such a way as to prevent contact with oxygen, e.g. in an ink jet printing cartridge. It is believed that this decomposition is due to minor amounts of impurities and/or by-products of the dye preparation process which are difficult to remove by commercial purification methods and it has been found that such decomposition can be reduced by the addition of an oxidising agent.
According to the present invention there is provided a composition of a water-soluble bis-azo dye of the Formula (1) and an oxidising agent, ##STR3## wherein A is optionally substituted phenyl or optionally substituted naphthyl; naphthylene; optionally substituted acyl; a group, -D-E; ##STR4## R.sup.4 & R.sup.5 each independently is H or optionally substituted alkyl; and optionally substituted acyl.
It is preferred that the compound of Formula (1) has at least as many carboxy (--COOH) groups as sulpho (--SO.sub.2 OH) groups, more preferably not more than 2 --SO.sub.2 OH groups and especially 1 or 2 --SO.sub.2 OH groups. It is preferred that the compound of Formula (1) has from 1 to 3, and especially 2 or 3--COOH groups. Overall it is preferred that the compound of Formula (1) contains a total of from 2 to 5 --COOH and --SO.sub.2 OH groups and especially 3 or 4 such groups.
When A is substituted it preferably carries from one to three, especially one or two substituents selected from: optionally substituted C.sub.1-4 -alkyl or optionally substituted aryl; and Q.sup.2 are each independently H or optionally substituted alkyl or optionally substituted aryl, or Q.sup.1 and Q.sup.2, taken together with the N atom to which they are attached, form an optionally substituted 5- or 6-membered ring; and aryl-sulphonylamino, more especially C.sub.1-4 -alkyl-CONH--or C.sub.14 -alkyl-SO.sub.2 NH--.
It is further preferred that A carries at least one, and more preferably, two carboxy groups. It is also preferred that R.sup.1 is H.
It is especially preferred that A is carboxyphenyl or carboxynaphthyl, especially 3- or 4-carboxyphenyl group or carboxyphenyl having one or two further substituents, especially one, selected from carboxy, sulpho, methyl, methoxy and chloro. Examples of optionally substituted phenyl and naphthyl groups represented by A are 4-carboxyphenyl, 3-carboxy-phenyl, 3,5-dicarboxyphenyl, 3,4-dicarboxyphenyl, 2-methyl-5-carboxy-phenyl, 2-sulpho-5-carboxyphenyl, 4-carboxynaphth-1-yl, 5-carboxynaphth-1-yl, 6-carboxynaphth-1-yl, 7-carboxynaphth-1-yl, 6-carboxynaphth-2-yl and 1-sulpho-6-carboxynaphth-2-yl.
When R.sup.2, R.sup.3, R.sup.6, R.sup.7, Q.sup.2 or Q.sup.2 is or includes optionally substituted alkyl it is preferably C.sub.1-4 -alkyl, such as methyl, ethyl, propyl or butyl; optionally substituted by C.sub.1-4 -alkoxy, especially methoxy or ethoxy; halo, especially chloro, OR.sup.8 ; COOR.sup.8 or --SO.sub.2 OH in which R.sup.8 is H, C.sub.1-4 -alkyl or phenyl. When R.sup.2, R.sup.3, R.sup.6, R.sup.7, Q.sup.1 or Q.sup.2 is or includes optionally substituted aryl this is preferably phenyl, optionally substituted, preferably in the 2-, 3-, 4-, 2,4-, 3,4- or 3,5- positions, by a group or groups selected from C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, halo, OH, NH.sub.2, CN, NO.sub.2, --COOH and --SO.sub.2 OH. When Q.sup.1 and Q.sub.2, taken together with the N atom to which they are attached, form an optionally substituted 5- or 6-membered ring this is
REFERENCES:
patent: 4400321 (1983-08-01), Linhart et al.
patent: 4765797 (1988-08-01), Hahnke et al.
Patent Abstracts of Japan, vol. 006, No. 261 (C-141), Dec. 21, 1982 & JP,A,57 153053--Sep. 21, 1982, see abstract.
Gregory Peter
Kenyon Ronald Wynford
Wight Paul
Powers Fiona T.
Zeneca Limited
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