Bleaching and dyeing; fluid treatment and chemical modification – Nontextile – dyeing process or product – including inorganic...
Patent
1998-08-24
2000-04-11
Einsmann, Margaret
Bleaching and dyeing; fluid treatment and chemical modification
Nontextile, dyeing process or product, including inorganic...
8922, 8924, 534734, D06P 500
Patent
active
060483709
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 prepharation 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 which are free from water-solubilising groups and have the formula: ##STR2## wherein: Q is --Br or --Cl; consisting of C.sub.1-6 -alkyl and aryl groups, each of which may be unsubstituted or substituted by one or more nonionic substituents; and l, --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.
Water solubilising groups which must be absent from the dyes of Formula 1 particularly include --SO.sub.3 H, --CO.sub.2 H, --PO.sub.3 H and quaternary ammonium groups and salts thereof.
When either or both of R.sup.1 and R.sup.2 represents a C.sub.3-6 alkyl group, the alkyl group can be linear or branched, and when branched, the branching may form a secondary or tertiary group. One or two points of branching may be present. The C--N bond can be formed between the N atom and any carbon in R.sup.1 or R.sup.2.
When either or both of R.sup.1 and R.sup.2 represents an aryl a group, the aryl group may be phenyl or naphthyl group, which may be substituted at any position relative to the bond to the N atom. When either or both of R.sup.1 and R.sup.2 represents a phenyl group, any substituents are preferably present ortho and/or para to the phenyl- N bond. In certain embodiments, R.sup.1 and R.sup.2 may be fused to form, together with the N atom, an aromatic or conjugated heterocyclic group, particularly one comprising a 5 or 6 membered ring, or a saturated heterocyclic group, particularly one comprising a 5, 6 or 7 membered ring.
The optional nonionic substituents for groups represented by R.sup.1 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, --OphenylSO.sub.2 F, --CO.sub.2 phenylSO.sub.2 F, --COOC.sub.1-6 -alkylOCOC.sub.1-6 -alkyl and --COOC.sub.1-6 -alkylCOOC.sub.1-6 -alkyl.
A preferred sub-group of the dyes of Formula 1comprises compounds of the formula: ##STR3## wherein Q is as defined above and each of R.sup.1 and R.sup.2, independently, is optionally substituted C.sub.1-6 -alkyl.
Within the sub-group of Formula 2, particular mention may be made of dyes in which each of R.sup.1 and R.sup.2 is optionally substituted ethyl, for exampie dyes in which R.sup.1 is --C.sub.2 H.sub.5 and R.sup.2 is --C.sub.2 H.sub.4 X wherein X is selected from --H, --CN, --COOC.sub.2 H.sub.5, --OCOCH.sub.3 and --OC.sub.6 H.sub.5.
The dyes of Formula 1 may be prepared by diazotising 6-bromo-2,5-dichloro4-fluorosuiphonylaniline or 2,3,6-trichloro-4-fluorosulphonylaniline and coupling the resulting diazo compound with an aromatic amine of the formula: ##STR4## 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 6-bromo-2,5-dichloro4-fluorosulphonylaniline or 2,3,6-trichioro-4-fluorosulphonylaniline may be diazotised in an acidic medium, such as acetic, propionic or hydrochloric acid using a nitrosating
REFERENCES:
patent: 5739299 (1998-04-01), Hall
BASF - Aktiengesellschaft
Einsmann Margaret
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