Colorant preparations

Details Colorant preparations Colorant preparations

2000-05-25

2003-08-19

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Organic additive for dye composition, dye composition...

Polymeric additive

C008S560000, C008S576000, C008S611000, C008S613000, C008S663000, C008S675000

Reexamination Certificate

active

06607565

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel dye preparations comprising, based on the weight of the preparation, from 0.1 to 30% by weight of one or more dyes selected from the class of the anthraquinones or quinophthalones which are free of ionic groups, from 0.1 to 20% by weight of a dispersant based on an arylsulfonic acid-formaldehyde condensation product or from 0.1 to 20% by weight of a water-soluble dispersant based on alkoxylated phenols, from 10 to 90% by weight of a mono- or polyhydric alcohol or mixtures thereof and optionally water, and to their use as inks in the inkjet process and for sublimation transfer printing.
2. Description of the Background
EP-A-655 527 discloses dye preparations comprising disperse dyes and specific dispersants. Prior patent application PCT/EP 97/02759 describes similar dye preparations.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide novel dye preparations comprising anthraquinone or quinophthalone dyes which are free of ionic groups. The novel dye preparations shall be advantageously useful for application in the inkjet process, particularly in the piezo or bubble jet process, for preparing prints on textile substrates and also in sublimation transfer printing.
We have found that this object is achieved by the dye preparations defined at the beginning.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Suitable anthraquinone dyes, which are free of ionic groups, conform for example to the formula I
where
L
1
is hydrogen, C
1
-C
10
-alkyl or unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, halogen- or nitro-substituted phenyl,
L
2
and L
3
are independently of each other hydrogen, unsubstituted or phenyl- or C
1
-C
4
-alkylphenyl-substituted C
1
-C
10
-alkoxy, unsubstituted or phenyl-substituted C
1
-C
10
-alkylthio, halogen, hydroxyphenyl, C
1
-C
4
-alkoxyphenyl, C
1
-C
6
-alkanoyl, C
1
-C
6
-alkoxycarbonyl or a radical of the formula
 where G
1
is oxygen or sulfur and G
2
is hydrogen or mono-C
1
-C
8
-alkylsulfamoyl whose alkyl chain is with or without interruption by 1 or 2 oxygen atoms in ether function, and
L
4
is unsubstituted or phenyl- or C
1
-C
4
-alkylphenyl-substituted amino, hydroxyl or unsubstituted or phenyl-substituted C
1
-C
10
-alkylthio.
Suitable quinophthalone dyes, which are free of ionic groups, conform for example to the formula II
where X is hydrogen, chlorine or bromine.
Any alkyl appearing in the abovementioned formula I may be straight-chain or branched.
In any substituted alkyl appearing in the abovementioned formula I the number of substituents is generally 1 or 2.
In any substituted phenyl appearing in the abovementioned formulae the number of substituents is generally from 1 to 3, preferably 1 or 2.
There follows an illustrative exemplification of radicals as defined in the 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, 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 each 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, butyryl, pentanoyl or hexanoyl.
Sulfamoyl is for example methylsulfamoyl, ethylsulfamoyl, propylsulfamoyl, isopropylsulfamoyl, butylsulfamoyl, pentylsulfamoyl, hexylsulfamoyl, heptylsulfamoyl, octylsulfamoyl, 2-ethylsulfamoyl, 2-methoxyethylsulfamoyl, 2-ethoxyethylsulfamoyl, 3,6-dioxaheptylsulfamoyl, 3,6-dioxaoctylsulfamoyl, 4,8-dioxanonylsulfamoyl, 3,7-dioxaoctylsulfamoyl, 3,7-dioxanonylsulfamoyl, 4,7-dioxaoctylsulfamoyl, 4,7-dioxanonylsulfamoyl or 4,8-dioxadecylsulfamoyl.
Preference is given to dye preparations comprising one or more anthraquinone dyes of the formula I where L
1
is hydrogen, C
1
-C
4
-alkyl or unsubstituted or methyl-substituted phenyl and L
4
is hydroxyl, amino or unsubstituted or methyl-substituted phenylamino.
Preference is further given to dye preparations comprising one or more anthraquinone dyes of the formula I where L
2
is C
1
-C
4
-alkoxy, acetyl, C
1
-C
4
-alkoxycarbonyl or a radical of the formula
where G
1
and G
2
are each as defined above, with G
1
being in particular oxygen and G
2
in particular hydrogen.
Preference is further given to dye preparations comprising the quinophthalone dye of the formula IIa
The dyes of the formulae I and II are generally known dyes. The anthraquinone dyes of the formula I are described for example in K. Venkataraman, The Chemistry of Synthetic Dyes, Vol. III, pages 391 to 413, Academic Press, New York, London, 1970. The quinophthalone dyes of the formula II are described for example in EP-A-83 553 or the literature cited therein.
Preference is given to dye preparations wherein 99% of the dye particles are smaller than 1 &mgr;m.
Preference is further given to dye preparations comprising dyes of the anthraquinone or quinophthalone series whose sublimation temperature is within the range from 140 to 300° C.
Preference is given to using a dispersant comprising an arylsulfonic acid-formaldehyde condensation product comprising from 3 to 50% by weight, based on the weight of the dispersant, of one or more aromatic or long-chain aliphatic carboxylic acids, their salts, their anhydrides or a mixture thereof.
The arylsulfonic acid-formaldehyde condensates used are in particular those having a maximum sulfonic acid group content of 40% by weight.
Suitable starting materials for the arylsulfonic acids include in particular a mixture of aromatic compounds obtainable by thermal cracking of a naphthenic residue oil and fractionation of the cracking products. Naphthenic residue oils are obtained for example in the cracking of light gasoline. In DE-A-2 947 005, for example, they are referred to as high boiling aromatic hydrocarbon oils. The naphthenic residue oil is preferably thermally cracked at from 1400 to 1700° C. The cracking products are then subjected to fractional distillation. The fraction passing over at atmospheric pressure (1013 mbar) at from 100 to 120° C. is collected and used as the aromatic compound for the sulfonation. Such a fraction is customarily obtained as a by-product in the known acetylene oil quench process (Ullmann's Encyclopedia of Industrial Chemistry, VCH Verlagsgesellschaft mbH, Weinheim, 1985, Volume A1, pages 107 to 112).
This aromatics fraction consists of a mixture of many aromatic substances whose structure and quantity can in practice not be determined in detail. The following aryl compounds are the chief representatives in this aromatics fraction:
% by weight in aro

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