Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-04-17
2000-02-08
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534DIG1, 534575, 8527, 8639, 8922, C09B 29033, C09B 2909, C09B 6722
Patent
active
060229578
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
Field of the Invention
This invention relates to azothiophenes, to mixtures thereof with other dyes and to a process for the coloration of synthetic textile materials with azothiophenes and said mixtures.
SUMMARY OF THE INVENTION
The present azothiophenes are not specifically disclosed but fall within the same general class of azothiophene dyes described in UK Patent 1394365 and further similar dyes are disclosed in EP 588489. The present azothiophenes have advantages in terms of light fastness, pH stability and strength over dyes disclosed in UK Patent 1394365 and EP588489.
According to the present invention, there is provided an azothiophene of Formula (1): ##STR2## in which R, R.sup.1, R.sup.2 and R.sup.3 each independently is alkyl or alkenyl.
The alkyl groups represented by R, R.sup.1, R.sup.2 and R.sup.3 are preferably C.sub.1-12 -alkyl, more preferably C.sub.1-6 -alkyl and especially C.sub.1-4 -alkyl. Those alkyl groups represented by R, R.sup.1, R.sup.2 and R.sup.3 which have three or more carbon atoms may be straight or branched chain alkyl groups. The alkenyl groups represented by R, R.sup.1, R.sup.2 and R.sup.3 are preferably C.sub.2-12 -alkenyl, more preferably C.sub.2-6 -alkenyl and especially C.sub.2-3 -alkenyl. Preferred azothiophene dyes of Formula (1) are those in which R.sup.1 and R.sup.2 each independently is C.sub.1-4 -alkyl or C.sub.2-3 -alkenyl and R and R.sup.3 each independently is C.sub.1-4 -alkyl. An especially preferred azothiophene of Formula (1) is that in which R.sup.1 and R.sup.2 are both ethyl and R and R.sup.3 are both methyl.
DETAILED DESCRIPTION OF THE INVENTION
The dyes of Formula (1) may be prepared by diazotising a 2-aminothiophene of Formula (2): ##STR3## and coupling the resulting diazo compound with an aromatic amine of Formula (3): ##STR4## in which R, R.sup.1, R.sup.2 and R.sup.3 are as hereinbefore defined. The diazotisation and coupling may be performed by conventionally used methods and the azothiophenes may be isolated using known techniques.
The azothiophenes of the present invention exist in various crystalline modifications and it is intended that the present definition of the azothiophenes includes such crystalline modifications which may be formed by established treatments such as heat treatment, solvent treatment, recrystallisation or seeding.
According to a further feature of the present invention, there is provided a mixture of dyes comprising an azothiophene of Formula (1) and an azothiophene of Formula (4): ##STR5## in which R.sup.4 is --CN, --Cl, --Br, --NO.sub.2, C.sub.1-4 -alkylcarbonyl, phenylcarbonyl, C.sub.1-4 -alkylsulphonyl, --COC.sub.1-4 -alkyl, --CONH.sub.2, --CONH(C.sub.1-4 -alkyl) or --CON(C.sub.1-4 -alkyl).sub.2 ; --COC.sub.1-4 -alkyl, --CONH.sub.2, --CONH(C.sub.1-4 -alkyl) or --CON(C.sub.1-4 -alkyl).sub.2 ; --NHCOC.sub.1-4 -alkyl or --NHSO.sub.2 C.sub.1-4 -alkyl; -alkenyl or C.sub.1-4 -alkyl substituted by --OH, C.sub.1-4 -alkoxy, --CN, phenyl, C.sub.1-4 -alkylCO--, C.sub.1-4 -alkoxyCO--, HOC.sub.1-4 -alkoxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxyCO--, --Cl or C.sub.1-4 -alkoxyCOO.
Preferred dyes of Formula (4) are those in which R.sup.4 is --NO.sub.2, --CN or C.sub.1-4 -alkylcarbonyl, R.sup.5 is --H or C.sub.1-4 -alkyl, R.sup.6 is --NO.sub.2 or --CN, R.sup.7 is C.sub.1-4 -alkyl or --NHCOC.sub.1-4 -alkyl, R.sup.8 is --H or C.sub.1-4 -alkoxy, R.sup.9 and R.sup.10 each independently is C.sub.1-4 -alkyl. Especially preferred dyes of Formula (4) are those in which R.sup.4 is --NO.sub.2, R.sup.5 is --H, R.sup.6 is --NO.sub.2, R.sup.7 is --CH.sub.3, --C.sub.2 H.sub.5, --NHCOCH.sub.3, --NHCOC.sub.2 H.sub.5, --NHCOC.sub.3 H.sub.7 or --NHCOCH(CH.sub.3).sub.3, R.sup.8 is --H or --OCH.sub.3 and R.sup.9 and R.sup.10 are both --C.sub.2 H.sub.5.
The dye mixtures may be prepared as physical mixtures, by co-crystallisation or co-synthesis.
Mixtures of dyes of Formulae (1) and (4) preferably comprise, on a weight basis, from 5% to 95% of a dye of Formula (1), and from 95% to 5% of a dy
REFERENCES:
patent: 4397781 (1983-08-01), Clark et al.
patent: 4472169 (1984-09-01), Shuttleworth et al.
patent: 4881943 (1989-11-01), Brierley et al.
patent: 4975410 (1990-12-01), Weber et al.
patent: 5779781 (1998-07-01), Gregory et al.
BASF - Aktiengesellschaft
Powers Fiona T.
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