Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-08-17
1999-12-07
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534581, 8531, 8532, 8662, 8922, 8924, C09B 29085, D06P 326, C08K 500
Patent
active
059985925
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 and other 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 and for the mass coloration of plastics 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 of the formula: ##STR2## wherein: R.sup.1 represents --C.sub.3 H.sub.6 CN, --C.sub.2 H.sub.4 Cl, --C.sub.3 H.sub.6 Cl, --C.sub.2 H.sub.4 OCOCH.sub.3 or --C.sub.2 H.sub.4 OCOCH.sub.2 Cl; and --SO.sub.2 F, or an organic moiety selected from the group consisting of C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-4 alkanoylamino, --NHSO.sub.2 alkyl, --NHCOC.sub.1-4 alkyl and -Ophenyl moieties, each organic moiety being unsubstituted or substituted by one or more nonionic substituents.
Those alkyl groups represented by R.sup.2 and R.sup.3 in Formula 1 which contain from 3 to 6 carbon atoms may be straight-chain or branched-chain alkyl groups but it is preferred that R.sup.2 is ethyl and that R.sup.3 is methyl.
Preferably at least one of R.sup.4 and R.sup.5 represents H, and particularly preferably both of R.sup.4 and R.sup.5 represent H. It is especially preferred that each of R.sup.4, R.sup.5 and R.sup.6 represents H.
The optional nonionic substituents for groups represented by R.sup.4 to R.sup.6 particularly include --CN, --OH, --OC.sub.1-6 -alkyl, --OCOC.sub.1-6 -alkyl, --COOC.sub.1-6 -alkyl, phenyl, phenoxy, --OCOphenyl, --OCOphenylSO.sub.2 F, phenylSO.sub.2 F, --CO.sub.2 phenylSO.sub.2 F
The dyes of Formula 1 may be prepared by diazotising 2,5-dichloro-4-fluorosulphonylaniline and coupling the resulting diazo compound with an aromatic amine of the formula: ##STR3## wherein R.sup.1 to R.sup.6 are as hereinbefore defined.
The diazotisation and coupling reactions may be performed using conditions conventionally employed for the type of reactant involved. Typically, the 2,5-dichloro4-fluorosulphonylaniline may be diazotised in an acidic medium, such as acetic, propionic or hydrochloric acid using a nitrosating agent such as nitrosylsulphuric acid, sodium nitrite or methyl nitrite at a temperature from -10.degree. C. to 10.degree. C. Coupling with the aromatic amine of Formula 2 may be achieved by adding the diazotised 2,5-dichloro4-fluorosulphonylaniline to the amine of Formula 2 in an alkanol, preferably a C.sub.1-4 alkanol, such as methanol at a temperature from 0.degree. C. to 10.degree. C. After coupling, the compound of Formula 1 may be recovered from the reaction mixture by any convenient means such as by filtration.
The azo compounds of Formula 1 are useful as disperse dyes and are valuable for colouring synthetic textile materials and fibre blends containing such materials.
The synthetic textile material may be selected from secondary cellulose acetate, cellulose triacetate, polyamide, polyacrylonitrile and aromatic polyester. The synthetic textile material is preferably polyamide such as polyhexamethylene adipamide or aromatic polyester, especially polyethylene terephthalate. Fibre blends may comprise mixtures of different synthetic textile materials or mixtures of synthetic and natural textile materials. Preferred fibre blends include those of polyester-cellulose such as polyester-cotton. The textile materials or blends thereof may be in the form of filaments, loose fibres, yarn or woven or knitted fabrics.
The azo compounds of Formula 1 or mixture thereof, optionally in conjunction with other disperse dyes, may be applied to the synthetic textile materials or fibre blends thereof by p
REFERENCES:
patent: 5739299 (1998-04-01), Hall
BASF - Aktiengesellschaft
Powers Fiona T.
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