Disazo fiber reactive dyestuffs

Details Disazo fiber reactive dyestuffs Disazo fiber reactive dyestuffs

1996-08-12

1997-10-14

Powers, Fiona T.

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

Organic compounds

Azo

534612, 8547, C09B 6209, D06P 1382

Patent

active

056774338

DESCRIPTION:

BRIEF SUMMARY
This application claims benefit of international application PCT/GB95/00083, filed Jan. 18, 1995.
This invention relates to organic chemicals, in particular to reactive dyes, their preparation and use.
According to the present invention there is provided a compound of Formula (1) and salts thereof: ##STR2## wherein: A is optionally substituted phenyl; or optionally substituted aryl, or attached from an optionally substituted piperidine or morpholine ring;
The optional substituents which may be present on A, E, R.sup.1, R.sup.2, R.sup.3 and Q are preferably selected from halo, especially chloro; nitro; C.sub.1-4 -alkyl; C.sub.1-4 -alkoxy; sulpho; carboxy; carbonamido; acylamino, especially acetamido; ureido; hydroxy; phosphato; sulphato; and amino.
A is preferably unsubstituted phenyl or phenyl having 1 or 2 substituents. When A is substituted it is preferred that it has at least one sulpho substituent. In an especially preferred embodiment A is 4-sulphophenyl.
Examples of groups represented by A include 2-, 3- and 4-sulphophenyl; 4-carboxy-2-sulphophenyl; 2,4-disulphophenyl; 2,5-disulphophenyl; 3,5-disulphophenyl; 2-sulpho-4-methoxyphenyl; 2-sulpho-4-methylphenyl; 3-nitrophenyl; 2-methoxy-4-sulphophenyl; 2-methyl-4-sulphophenyl; 4-chloro-2-sulphophenyl; and 2,5-dichloro-4-sulphophenyl.
E is preferably optionally substituted 1,4-phenylene, especially 1,4-phenylene which is unsubstituted or substituted by 1 or 2 of the aforementioned optional substituents, preferably by 1 or 2 groups selected from halo, sulpho, C.sub.1-4 -alkoxy and C.sub.1-4 -alkyl- When E is substituted it preferably has at least one sulpho substituent.
R.sup.1 is preferably H or C.sub.1-4 -alkyl, more preferably C.sub.1-4 -alkyl, especially methyl or ethyl. The preference for R.sup.1 being C.sub.1-4 -alkyl arises from the surprising finding that this can lead to improved wash-off properties in the dye.
R.sup.2 is preferably H, optionally substituted C.sub.1-4 -alkyl, more preferably H or C.sub.1-4 -alkyl, especially methyl or ethyl.
R.sup.3 is preferably H, optionally substituted alkyl, optionally substituted phenyl or C.sub.1-4 -alkoxy, more preferably H, optionally substituted C.sub.1-4 -alkyl, phenyl or sulphophenyl, especially H, methyl or ethyl.
Examples of groups represented by R.sup.2 and R.sup.3 include --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH.sub.2 CO.sub.2 H, --CH.sub.2 CH.sub.2 SO.sub.3 H, --CH.sub.2 CH.sub.2 OSO.sub.3 H, --(CH.sub.2).sub.3 CO.sub.2 H, --CH.sub.2 CO.sub.2 H, --CH.sub.2 PO.sub.3 H.sub.2, --CH(CO.sub.2 H)CH.sub.2 CO.sub.2 H, --CH(CO.sub.2 H)CH.sub.2 CH.sub.2 CO.sub.2 H, 4- sulphophenyl, 3-sulphophenyl, 2,5- and 2,6-disulphophenyl, --OCH.sub.3 and --(CH.sub.2).sub.2 CH.sub.3.
Preferably R.sup.2 and R.sup.3 are free from groups which, on treatment with aqueous alkali, yield groups of formula --SO.sub.2 CH.dbd.CH.sub.2. Thus R.sup.2 and R.sup.3 preferably do not contain groups of formula --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, --SO.sub.2 CH.sub.2 CH.sub.2 Cl or salts thereof.
In one preferred embodiment R.sup.2 and R.sup.3 are each independently H, C.sub.1-4 -alkyl or C.sub.1-4 -alkyl having an --OH group, or R.sup.2 and R.sup.3 taken together with the N atom to which they are attached form an optionally substituted piperidine or morpholine ring. Such compounds have particularly good build-up in exhaust dyeing.
Q is preferably pyridinium having 1 or 2 substituents selected from carboxy, C.sub.1-4 -alkyl and carbonamido (i.e. CONH.sub.2). Examples of groups represented by Q include 3- and 4-carboxypyridinium, pyridinium, 3-methylpyridinium , 3- and 4-carbonamidopyridinium .
The --NR.sup.1 -- group shown in Formula (1) is preferably at the 6- position on the naphthalene ring relative to the hydroxy group. When the --N.sup.1 -- group shown in Formula (1) is at the 6-position on the naphthalene ring relative to hydroxy group it is preferred that m has a value of 0.
The compound is preferably in salt form, for example in the form of a sodium, lithium, potassium, ammonium or substituted amm

REFERENCES:
patent: 4626589 (1986-12-01), Omura et al.
patent: 4693726 (1987-09-01), Meininger
patent: 5116956 (1992-05-01), Miyamoto et al.

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