Azo compound

Details Azo compound Azo compound

1998-11-03

1999-10-19

Powers, Fiona T.

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

Organic compounds

Azo

534797, 534834, 8543, 8641, 106 3147, 106 3149, 106 3152, C09B 3108, C09B 62513, C09B 6722, C09D 1100

Patent

active

059691140

DESCRIPTION:

BRIEF SUMMARY
This invention relates to coloured bisazo compounds and aqueous solutions thereof suitable for use in the coloration of substrates, especially sheet materials such as paper, and especially by ink jet printing.
According to the present invention there is provided a compound of Formula (1) and salts thereof: ##STR1## wherein: J is --OR.sup.4 or --NR.sup.4 R.sup.5 ; form a 5- or 6-membered carbocyclic group optionally containing a ring oxygen atom; naphthylene; ##STR2## wherein R.sup.2 & R.sup.3 each independently is H, --COOH or --SO.sub.3 H; optionally optionally substituted
R.sup.1 is H or optionally substituted alkyl, alkylcarbonyl, alkylsulphonyl, alkoxycarbonyl, alkoxysulphonyl, arylcarbonyl or arylsulphonyl; Q.sup.2 ;
Q.sup.1 & Q.sup.2 each independently is H, optionally substituted C.sub.1-4 -alkyl or 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 carbocyclic group optionally containing a ring oxygen atom.
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 naphthalene. Substituents on A are preferably selected from: ; 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.
In the naphthylene group of Formula (1a) 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.3 is H and R.sup.2 is --COOH or --SO.sub.3 H and in the other R.sup.2 is H and R.sup.3 is --COOH or --SO.sub.3 H. It is preferred that Z.sup.2 is H, methyl, methoxy, --SO.sub.3 H, --OH and more especially H.
In the phenylene group of Formula (1b) wherein Z.sup.1 is --NZ.sup.3 Z.sup.4 it is preferred that Z.sup.3 is H or C.sub.1-4 -alkyl, such as methyl or ethyl. It is especially preferred that Z.sup.3 is H. Where Z.sup.4 is alkyl this is preferably C.sub.1-4 -alkyl. Where R.sup.4 or Z.sup.4 is acyl this is preferably NH.sub.2 CO--, R.sup.7 CO--or R.sup.7 SO.sub.2 --, wherein R.sup.7 is as hereinbefore defined. Where Z.sup.4 is other than H, and especially where it is acyl, Z.sup.3 is preferably H. It is especially preferred that --NZ.sup.3 Z.sup.4 is --NH.sub.2.
In the phenylene group of Formula (1b) wherein is Z.sup.1 optionally substituted alkyl or optionally substituted alkoxy, it is preferred that Z.sup.1 is C.sub.1-4 -alkyl such as methyl or ethyl or C.sub.1-4 -alkoxy such as methoxy or ethoxy and it is especially preferred that Z.sup.1 is H, methyl or methoxy.
In the phenylene group of Formula (1b) it is preferred that Z.sup.2 is C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, --Cl, --H, --COOH or --SO.sub.3 H, more preferably C.sub.1-4 -alkyl, such as methyl or ethyl, or C.sub.1-4 -alkoxy, such as methoxy or ethoxy and it is especially preferred that Z.sup.2 is H, methyl or methoxy.
The C.sub.2-6 -alkylene group represented by B is preferably a C.sub.2 - or C.sub.3 -alkylene group optionally substituted by a group listed below as an optional substituent fo

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, 43-49.

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