Dye preparations

Compositions: coating or plastic – Coating or plastic compositions – Marking


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106 3147, C09D 1102





The present invention relates to novel dye compositions comprising, based on the weight of the composition, from 0.1 to 30 wt % of one or more dyes selected from the class of the anthraquinones or quinophthalones which are free from ionic groups, from 0.1 to 20 wt % of a dispersant based on an arylsulfonic acid-formaldehyde condensation product and, optionally, water, and to their use as inks in the inkjet and sublimation transfer printing processes.
EP-A 655,527 discloses dye compositions comprising disperse dyes and specific dispersants.
It is an object of the present invention to provide novel dye compositions comprising anthraquinone or quinophthalone dyes which are free from ionic groups. The novel dye compositions are to be suitable for improved use in the inkjet process and also in the sublimation transfer printing process.
Accordingly, we have found the dye compositions defined above.
Suitable anthraquinone dyes free from ionic groups conform for example to formula I ##STR1## in which L.sup.1 denotes hydrogen, C.sub.1 -C.sub.10 alkyl or phenyl optionally substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or nitro, optionally substituted by phenyl or C.sub.1 -C.sub.4 alkylphenyl; C.sub.1 -C.sub.10 alkylthio optionally substituted by phenyl; halogen; cyano; hydroxyphenyl; C.sub.1 -C.sub.4 alkoxyphenyl; C.sub.1 -C.sub.6 alkanoyl; C.sub.1 -C.sub.6 alkoxycarbonyl or a radical of the formula ##STR2## in which G.sup.1 denotes oxygen or sulfur and G.sup.2 denotes hydrogen or mono-(C.sub.1 -C.sub.8 alkyl)sulfamoyl whose alkyl chain may be interrupted by 1 or 2 oxygen atoms in ether function, and phenyl or C.sub.1 -C.sub.4 alkylphenyl; hydroxyl; or C.sub.1 -C.sub.10 alkylthio optionally substituted by phenyl.
Suitable quinophthalone dyes free from ionic groups conform for example to formula II ##STR3## in which X denotes hydrogen, chlorine or bromine.
Any alkyl appearing in the above formula I may be linear or branched.
In any substituted alkyl appearing in the above formula I the number of substituents is usually 1 or 2.
In any substituted phenyl appearing in the above formulas the number of substituents is generally from 1 to 3, preferably 1 or 2.
The following is an exemplary list of radicals as defined in formula I.
Alkyl is for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl or isodecyl (the designations isooctyl, isononyl and isodecyl are trivial names derived from the oxo process alcohols--cf. Ullmann's Encyclopedia of Industrial Chemistry, .sub.5 th Edition, Vol. A 1, pages 290 to 293, and also Vol. A 10, pages 284 and 285).
Phenyl is for example phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4-isopropylphenyl, 2-, 3- or 4-butylphenyl, 2,3-, 2,4- or 2,6-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 2,3-, 2,4-or 2,6-dimethoxyphenyl, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-bromophenyl or 2-, 3- or 4-nitrophenyl.
Alkylthio and phenylthio are for example methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, pentylthio, hexylthio, heptylthio, octylthio, isooctylthio, 2-ethylhexylthio, nonylthio, isononylthio, decylthio, isodecylthio, benzylthio or 1- or 2-phenylethylthio.
Alkoxy is for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, 2-methylpentyloxy, heptyloxy, octyloxy, isooctyloxy, 2-ethylhexyloxy, nonyloxy, isononyloxy, decyloxy, isodecyloxy, benzyloxy or 1- or 2-phenylethoxy.
Halogen is for example fluorine, chlorine or bromine.
Alkoxycarbonyl is for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl or hexyloxycarbonyl.
Alkanoyl is for example formyl, acetyl, propionyl, bu

patent: 3660008 (1972-05-01), Kissa
patent: 3765835 (1973-10-01), Clarke et al.
patent: 4110073 (1978-08-01), Mollet et al.
patent: 4427413 (1984-01-01), Bauerle
patent: 5186846 (1993-02-01), Brueckmann et al.
The Chemistry of Synthetic Dyes, vol. III, pp. 391 to 413, Academic Press, New York, London, 1970, no month.
Ullmann's Encyclopedia of Industrial Chemistry, VCH Verlagsgesellschaft mbH, Weinheim, 1985, vol. A1, pp. 107 to 112, no month.
Text. Chem. Color 19, (1987), No. 8, 23-29, no month.
Text. Chem. Color 21, 1989, No. 6, 27-32, no month.
Ullmann's Encyclopedia of Industrial Chemistry, 5.sup.th Edition, vol. A26, pp. 499 to 501, no date avail.
Chemical Abstracts, vol. 106, No. 10, Mar. 9, 1987, & JP 61 148 275 A (Mitsubishi Chemical Industries Co.) Jul. 5, 1986.


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