Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1997-01-30
1998-05-26
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534797, 534832, 106 3148, 106 3152, C09B 3108, C09D 1100
Patent
active
057566933
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a coloured disazo 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 a first aspect of the present invention there is provided a compound of the Formula (1) and salts thereof: ##STR2## wherein: A is optionally substituted phenyl or optionally substituted naphthyl; optionally substituted alkoxy, or optionally substituted alkylthio; substituted alkyl;
It is preferred that the compound of Formula (1) or (2) has at least as many carboxy (--COOH) groups as sulpho (--SO.sub.2 OH) groups, more preferably not more than 2 sulpho groups and especially only a single sulpho group. It is also preferred that the compound of Formula (1) or (2) has from 1 to 5, more preferably from 1 to 3, and especially 2 or 3 carboxy groups.
When A is substituted it preferably carries from one to three, especially one or two, substituents selected from: substituted C.sub.1-4 -alkyl or optionally substituted aryl; Q.sup.2 are each independently H or optionally substituted alkyl or 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, especially an optionally substituted morpholine or piperidine ring; and aryl-sulphonylamino, more especially C.sub.1-4 -alkyl--CONH--or C.sub.1-4 -alkyl-SO.sub.2 NH--. substituent.
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-carboxy-phenyl, 3-carboxy-phenyl, 3,5-dicarboxy-phenyl, 3,4-dicarboxyphenyl, 2-methyl-5-carboxy-phenyl, 2-methoxy-5-carboxyphenyl, 2-chloro-5-carboxyphenyl, 3- and 4-amino-5-carboxyphenyl, 2-sulpho-5-carboxy-phenyl, 4-carboxynaphth-1-yl, 5-carboxynaphth-1-yl, 6-carboxy-naphth-1-yl, 7-carboxynaphth-1-yl, 6-carboxynaphth-2-yl and -sulpho-6-carboxynaphth-2-yl.
When R.sup.6, Q.sup.1 or Q.sup.2 is optionally substituted alkyl it is preferably C.sub.1-4 -alkyl, such as methyl, ethyl, propyl or butyl optionally carrying a hydroxy or amino group. When R.sup.6, Q.sup.1 or Q.sup.2 is optionally substituted aryl it is preferably phenyl.
R.sup.2 is preferably C.sub.1-4 -alkyl, especially methyl or ethyl; C.sub.1-4 -alkoxy, especially methoxy or ethoxy, C.sub.1-4 -alkylthio, especially methylthio; Cl; H; COOH; or SO.sub.2 OH. R.sup.3 is preferably H or C.sub.1-4 -alkyl, more preferably H, methyl or ethyl.
Where R.sup.4 or R.sup.5 is alkyl it is preferably C.sub.1-4 -alkyl. Where one of R.sup.4 and R.sup.5 is C.sub.1-4 -alkyl, the other is preferably H, although it is further preferred that both of R.sup.4 and R.sup.5 are H.
Where Q.sup.1, Q.sup.2, R.sup.2, R.sup.3, R.sup.4, R.sup.5 or R.sup.6 is substituted alkyl or substituted alkoxy, or Q.sup.1 and Q.sup.2 form a ring, the substituent(s) is preferably selected from --COOH, --SO.sub.2 OH, OH, NH.sub.2, C.sub.1-4 -alkoxy and halo, especially chloro. Where R.sup.6, Q.sup.1 or Q.sub.2 is substituted aryl it is preferably phenyl and the substituent(s) is preferably in the 2-, 4-, 2,4-, 3,4- and 3,5-position(s) and selected from --COOH; --SO.sub.2 OH; OH; NH.sub.2, CN; NO.sub.2 ; C.sub.1-4 -alkyl; C.sub.1-4 -alkoxy; and halo, especially chloro.
The optionally substituted phenyl group represented by B may carry one or more substituents selected from the same group as the optional substituents on A, especially sulpho; carboxy; C.sub.1-4 -alkyl; C.sub.1-4 -alkoxy; and chloro. The optionally substituted alkyl group represented by B is preferably C.sub.1-4 -alkyl which may be unsubstituted or may carry one or more substituents selected from --SO.sub.2 OH, OH, C.sub.1-4 -alkoxy, amino, especially NH.sub.2, and halo, and more especially, --COOH. It is preferred that B is H, unsubstituted phenyl or C.sub.1-4 -alkyl o
REFERENCES:
patent: 4626284 (1986-12-01), Ohta et al.
patent: 4724001 (1988-02-01), Ohta et al.
patent: 5198022 (1993-03-01), Aulick et al.
patent: 5354369 (1994-10-01), Shimomura et al.
patent: 5437716 (1995-08-01), Sano et al.
patent: 5478384 (1995-12-01), Takimoto et al.
Miura et al: "Water-soluble disazo compounds", Chemical Abstracts, vol. 106, No. 4, Jan. 26, 1987. abstract No. 19955u, p. 66, see abstract & JP,A,62 057 650 (Mitsubishi Chemical Industries Co., Ltd.) Mar. 24, 1986, see compounds 10,11,13,15,19,22,27,32; p. 5, formula VII.
Gregory Peter
Kenyon Ronald Wynford
Powers Fiona T.
Zeneca Limited
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