Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1999-03-05
1999-10-26
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534733, 534734, C09B 29085, C09B 2909, D06P 326
Patent
active
059731273
DESCRIPTION:
BRIEF SUMMARY
This invention relates to azo dyes and more particularly to water-insoluble monoazo dyes containing the fluorosulphonyl group, to a method for their preparation and to their use for colouring synthetic textile materials.
Our International patent application published as WO 95/20014 describes azo compounds which contain at least one fluorosulphonyl group and are free from water-solubilising groups. The use of these compounds for colouring synthetic textile materials is also described.
It has now been found that certain dyes falling within the general class described in WO 95/20014 but not specifically disclosed therein exhibit advantageous properties when applied as disperse dyes to synthetic textile materials.
Thus, according to the invention, there are provided monoazo dyes which are free from water-solubilising groups and have the formula: ##STR2## wherein A represents an optionally substituted aromatic carbocyclic or heterocyclic radical, n represents an integer from 0 to 3, X represents a halogen atom and each of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5, independently, represents hydrogen or a substituent, at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 or a substituent on A being --SO.sub.2 F or a substituent to which at least one --SO.sub.2 F group is attached.
The dyes of Formula 1 preferably have low solubility in water, typically less than 1%, preferably less than 0.5% and especially less than 0.2% on a weight basis. They are thus free from water-solubilising groups such as sulphonate, carboxylate, phosphonate and quaternary amino groups.
Heterocyclic groups which may be represented by A in the dyes of Formula 1 include thienyl, thiazolyl, isothiazolyl, pyrazolyt, imidazolyl, pyridyl, pyridonyl, 1,2,4- and 1,3,4-thiadiazolyl, furanyl, pyrrolyl, pyridazyl, pyrimidyl, pyrazinyl, benzothiazolyl, benzoisothiazolyl, quinolinyl, isoquinolinyl, indolyl, pyridothiazolyl, pyridoisothiazolyl, 1,2,3-triazolyl and 1,2,4-triazolyl. Carbocyclic groups which may be represented by A include phenyl and naphthyl.
A is preferably thienyl, phenyl, naphthyl, thiazolyl, isothiazolyl, pyridonyl, quinolinyl, more preferably thien-2-yl, phenyl, naphth-1-yl, naphth-2-yl, thiazol-2-yl, isothiazol-5-yl, pyrid-4-on-5-yl or quinolinyl. A is especially preferably thien-2-yl or phenyl.
Examples of suitable substituents for A include cyano, hydroxy, nitro, fluoro, chloro, bromo, iodo, fluorosulphonyl, trifluoromethyl, alkyl, alkoxy, aryl, aryloxy, fluorosulphonylaryl, fluorosulphonylaryloxy, --CO-alkyl, --COO-alkyl, --OCO-alkyl, --CO-aryl, --COO-aryl, --OCO-aryl, --NHCO-alkyl, --NHCO-aryl, --NHSO.sub.2 -alkyl, --NHSO-.sub.2 aryl, --S-alkyl, --S-aryl, --SO.sub.2 -alkyl, --SO.sub.2 -aryl, --SCN or NR.sup.6 R.sup.7 in which R.sup.6 and R.sup.7 each independently is --H, alkyl, aryl or cycloalkyl.
In all of the suitable substituents for A.sub.1 each alkyl is preferably C.sub.1-10 -alkyl, each alkoxy is preferably C.sub.1-10 -alkoxy and those groups having three or more carbon atoms may be straight or branched chain. Each aryl is preferably phenyl or naphthyl and each alkyl, alkoxy or aryl group may carry an --SO.sub.2 F substituent. R.sup.6 and R.sup.7 together with the --N atom to which they are attached may form a 5- or 6-membered ring such as morpholino or piperidino.
Preferred substituents for A include cyano, nitro, chloro, bromo, fluorosulphonyl, --C.sub.1-6 -alkyl, --C.sub.1-6 -alkoxy, --COC.sub.1-6 -alkyl, --NHCOC.sub.1-6 -alkyl, --OCOC.sub.1-6 -alkyl, --COOC-.sub.1-6 -alkyl, phenoxy, 4-SO.sub.2 F-phenyl and 4-SO.sub.2 F-phenoxy.
Substituents which may be represented by R.sup.1 and R.sup.2 include alkyl and aryl groups which may optionally be substituted by --OH, --CN, --F, --Cl, --Br, --I, --SO.sub.2 F, alkoxy, alkenyl, phenyl, phenyl-SO.sub.2 F, aryloxy, aryloxy-SO.sub.2 F, --N(alkyl).sub.2, --OCO-alkyl, --OCO-alkyl-Cl, --COO-alkyl, --COO-alkyl-OH, --COO-alkyl-CN, --COO-alkyl-CO-alkyl, --COO-alkylphenyl, --OCO-phenyl, --CO-phenyl-SO.sub.2 F, --OCO-phenyl-NO.sub.2, --OCO-phenylalkyl, --OCO-phenylalkoxy,
REFERENCES:
patent: 3398135 (1968-08-01), Mueller
patent: 3406164 (1968-10-01), Altermatt et al.
patent: 3428622 (1969-02-01), Altermatt et al.
patent: 3980636 (1976-09-01), Weaver et al.
patent: 5739299 (1998-04-01), Hall
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Powers Fiona T.
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