Disazo compounds containing a piperazinylethysulfonyl group

Details Disazo compounds containing a piperazinylethysulfonyl group Disazo compounds containing a piperazinylethysulfonyl group

1999-04-21

1999-12-28

Powers, Fiona T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

534797, 8639, 106 3147, C09B 3108, C09B 6722, C09B 62513, C09D 1100

Patent

active

06008331&

DESCRIPTION:

BRIEF SUMMARY
This application is the national phase of international application PCT/GB97/00482 filed Feb. 21, 1997 which designated the U.S.
This invention relates to a coloured bisazo compound and aqueous solutions thereof suitable for use in the coloration of substrates, especially sheet materials such as paper, and especially by a printing process such as ink jet printing.
According to the present invention there is provided a compound of Formula (1) or a salt thereof: ##STR3## wherein: J is a group of the Formula (1a): ##STR4## wherein: ##STR5## wherein


______________________________________ R.sup.2 & R.sup.3 each independently is H, --COOH or --SO.sub.3 H; Z.sup.1 & Z.sup.5 each independently is H, optionally substituted alkyl, optionally substituted alkoxy or --NZ.sup.3 Z.sup.4 ; Z.sup.2 is H, halo, --COOH, --SO.sub.3 H, --OH, optionally substituted alkyl, optionally substituted alkoxy or optionally substituted alkylthio; Z.sup.3 is H or optionally substituted alkyl; Z.sup.4 is H, optionally substituted alkyl or acyl; R.sup.1 is H, optionally substituted alkyl, alkylcarbonyl, alkylsulphony l, alkoxycarbonyl, alkoxysulphonyl, arylcarbonyl or arylsulphonyl; T & T.sup.1 each independently is H or --SO.sub.3 H; R is H, optionally substituted alkyl, optionally substituted aryl, or a group --B--NQ.sup.1 Q.sup.2 ; B is optionally substituted C.sub.2-6 -alkylene; and Q.sup.1 & each independently is H, optionally substituted C.sub.1-4 -alkyl or Q.sup.2 Q.sup.1 and Q.sup.2 together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring. ______________________________________
When A is phenylene it is preferably phen-1,3-ylene or phen-1,4-ylene and when A is naphthylene it is preferably naphth-1,4-ylene or naphth-1,5-ylene.
When A is substituted it preferably carries from one to three, especially one or two substituents, preferably in the 2-, 3-, 4-, 2,4-, 3,4-, 2,5- or 3,5- positions when A is phenylene or in the 4-, 5-, 6-, 7-, 8-, 4,5-, 4,8-, 5,8-, or 6,7- positions when A is naphthylene Substituents on A are preferably selected from: --B(OH).sub.2 ;
--SO.sub.2 R.sup.7, --COOR.sup.7, --SO.sub.2 R.sup.7 or --COR.sup.7, wherein R.sup.7 is optionally substituted C.sub.1-4 --alkyl or optionally substituted aryl, especially phenyl; and aryl-sulphonylamino, and more especially C.sub.1-4 -alkyl-CONH--or C.sub.1-4 -alkyl-SO.sub.2 NH--.
It is preferred that A is unsubstituted phen-1,4-ylene or naphth-1,4-ylene, or that it carries one or two substituents, more especially one, selected from --COOH, --SO.sub.3 H, methyl, methoxy and chloro. Examples of preferred and especially preferred optionally substituted phenylene and naphthylene groups represented by A are phen-1,4-ylene, phen-1,3-ylene, 2-methylphen-1,4-ylene, 2-methoxyphen-1,4-ylene, 3-methyl-phen-1,4-ylene, 2-sulphophen-1,4-ylene, naphth-1,4-ylene and naphth-1,5-ylene.
The group of Formula (1a) may be free from ionisable groups or it may carry an ionisable group. When the group of Formula (1a) is free from ionisable groups R.sup.6 is preferably one of the groups mentioned above in relation to R.sup.6 other than --COOH --SO.sub.3 H. When the group of Formula (1a) bears an ionisable group it is preferred that R.sup.6 is an ionisable group e.g. R.sup.6 can be COOH; --SO.sub.3 H; or alkyl, aryl, arylcarbonyl or arylsulphonyl, alkoxycarbonyl, alkoxysulphonyl, arylcarbonyl or arylsulphonyl, each of which is optionally substituted and each of which carries at least one ionisable group.
Preferably the group of Formula (1a) carries a carboxy group because this leads to dyes having a high optical density.
In the naphthylene group of Formula (1b) it is preferred that one of R.sup.2 and R.sup.3 is H and the other is H, --COOH or --SO.sub.3 H. Where one of R.sup.2 and R.sup.3 is --COOH or --SO.sub.3 H and the other is H, it is convenient to employ a mixture of isomeric compounds in one of which R.sup.2 is --COOH or --SO.sub.3 H and R.sup.3 is H and in the other R.sup.2 is H and R.sup.3 is --COOH or

REFERENCES:
patent: 3951591 (1976-04-01), Birke et al.
patent: 5102459 (1992-04-01), Ritter et al.
Beech, W.F., Fibre-Reactive Dyes, Logos Press Limited, London, Great Britain, 1970, 220-221.
Venkataraman, K., The Chemistry of Synthetic Dyes, Academic Press, New York, 1972, vol. VI, 43-45.

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