Pigment preparations with radiation curable binder suitable...

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...

Reexamination Certificate

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C522S070000, C522S084000, C522S086000, C522S074000, C522S082000, C106S031600, C106S031870

Reexamination Certificate

active

06294592

ABSTRACT:

The present invention relates to novel pigment preparations comprising
A) at least one finely divided, organic or inorganic pigment,
B) a dispersant based on arylsulfonic acid/formaldehyde condensation products or on alkoxylated phenols,
C) a radiation-curable binder,
D) if desired, a photoinitiator, and
E) water
as essential constituents.
This invention further relates to the use of these pigment preparations as inks in the ink-jet process and to a process for printing sheetlike or three-dimensionally configured substrates by the ink-jet process using these pigment preparations.
Inks for use in the ink-jet process have to meet a whole series of requirements: They have to have a viscosity and surface tension suitable for printing, they have to be stable in storage, ie. they should not coagulate and the dispersed, undissolved colorant should not settle out, they must not lead to blockage of the printer nozzle, which can likewise be problematical especially in the case of pigmented inks, ie. inks comprising dispersed colorant particles, and finally they should be environmentally compatible, ie. be substantially based on water as liquid phase and include organic solvents only in small amounts, if at all. In addition, the prints obtained have to meet coloristic requirements, ie. show brilliance and depth, and have good fastness properties, eg. rub fastness, light fastness and water fastness or wash fastness in the case of textile printing.
EP-A-658 607 and JP-A-48922/1996 disclose aqueous UV-curable inks which differ from the pigment preparations of the present invention, not least because of the dispersant.
It is an object of the present invention to provide novel pigment preparations having advantageous application properties for the ink-jet process.
We have found that this object is achieved by the pigment preparations defined at the beginning.
The pigment preparations of the invention comprise a finely divided, organic or inorganic pigment. The expression “organic pigment” includes vat dyes. The pigment preparations of the invention may also comprise mixtures of various organic or various inorganic pigments or of organic and inorganic pigments.
Examples of suitable pigments (A) are:
organic pigments:
monoazo pigments:
C.I. Pigment Brown 25;
C.I. Pigment Orange 5, 13, 36 and 67;
C.I. Pigment Red 1, 2, 3, 5, 8, 9, 12, 17, 22, 23, 31, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 52:1, 52:2, 53, 53:1, 53:3, 57:1, 63, 251, 112, 146, 170, 184, 210 and 245;
C.I. Pigment Yellow 1, 3, 73, 74, 65, 97, 151 and 183;
disazo pigments:
C.I. Pigment Orange 16, 34 and 44;
C.I. Pigment Red 144, 166, 214 and 242;
C.I. Pigment Yellow 12, 13, 14, 16, 17, 81, 83, 106, 113, 126, 127, 155, 174, 176 and 188;
anthanthrone pigments:
C.I. Pigment Red 168 (C.I. Vat Orange 3);
anthraquinone pigments:
C.I. Pigment Yellow 147 and 177;
C.I. Pigment Violet 31;
anthrapyrimidine pigments:
C.I. Pigment Yellow 108 (C.I. Vat Yellow 20);
quinacridone pigments:
C.I. Pigment Red 122, 202 and 206;
C.I. Pigment Violet 19;
quinophthalone pigments:
C.I. Pigment Yellow 138;
dioxazine pigments:
C.I. Pigment Violet 23 and 37;
flavanthrone pigments:
C.I. Pigment Yellow 24 (C.I. Vat Yellow 1);
indanthrone pigments:
C.I. Pigment Blue 60 (C.I. Vat Blue 4) and 64 (C.I. Vat Blue 6);
isoindoline pigments:
C.I. Pigment Orange 69;
C.I. Pigment Red 260;
C.I. Pigment Yellow 139 and 185;
isoindolinone pigments:
C.I. Pigment Orange 61;
C.I. Pigment Red 257 and 260;
C.I. Pigment Yellow 109, 110, 173 and 185;
isoviolanthrone pigments:
C.I. Pigment Violet 31 (C.I. Vat Violet 1);
metal complex pigments:
C.I. Pigment Yellow 117, 150 and 153;
C.I. Pigment Green 8;
perinone pigments:
C.I. Pigment Orange 43 (C.I. Vat Orange 7);
C.I. Pigment Red 194 (C.I. Vat Red 15);
perylene pigments:
C.I. Pigment Black 31 and 32;
C.I. Pigment Red 123, 149, 178, 179 (C.I. Vat Red 23), 190 (C.I. Vat Red 29) and 224;
C.I. Pigment Violet 29;
phthalocyanine pigments:
C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6 and 16;
C.I. Pigment Green 7 and 36;
pyranthrone pigments:
C.I. Pigment Orange 51;
C.I. Pigment Red 216 (C.I. Vat Orange 4);
thioindigo pigments:
C.I. Pigment Red 88 and 181 (C.I. Vat Red 1);
C.I. Pigment Violet 38 (C.I. Vat Violet 3);
triarylcarbonium pigments:
C.I. Pigment Blue 1, 61 and 62;
C.I. Pigment Green 1;
C.I. Pigment Red 81, 81:1 and 169;
C.I. Pigment Violet 1, 2, 3 and 27;
C.I. Pigment Black 1 (aniline black);
C.I. Pigment Yellow 101 (aldazine yellow);
C.I. Pigment Brown 22;
vat dyes (in addition to those already mentioned above):
C.I. Vat Yellow 2, 3, 4, 5, 9, 10, 12, 22, 26, 33, 37, 46, 48, 49 and 50;
C.I. Vat Orange 1, 2, 5, 9, 11, 13, 15, 19, 26, 29, 30 and 31;
C.I. Vat Red 2, 10, 12, 13, 14, 16, 19, 21, 31, 32, 37, 41, 51, 52 and 61;
C.I. Vat Violet 2, 9, 13, 14, 15, 17 and 21;
C.I. Vat Blue 1 (C.I. Pigment Blue 66), 3, 5, 10, 12, 13, 14, 16, 17, 18, 19, 20, 22, 25, 26, 29, 30, 31, 35, 41, 42, 43, 64, 65, 66, 72 and 74;
C.I. Vat Green 1, 2, 3, 5, 7, 8, 9, 13, 14, 17, 26, 29, 30, 31, 32, 33, 40, 42, 43, 44 and 49;
C.I. Vat Brown 1, 3, 4, 5, 6, 9, 11, 17, 25, 32, 33, 35, 38, 39, 41, 42, 44, 45, 49, 50, 55, 57, 68, 72, 73, 80, 81, 82, 83 and 84;
C.I. Vat Black 1, 2, 7, 8, 9, 13, 14, 16, 19, 20, 22, 25, 27, 28, 29, 30, 31, 32, 34, 36, 56, 57, 58, 63, 64 and 65;
inorganic pigments:
white pigments:
titanium dioxide (C.I. Pigment White 6), zinc white, pigment grade zinc oxide; zinc sulfide, lithopone; lead white;
black pigments:
iron oxide black (C.I. Pigment Black 11), iron manganese black, spinel black (C.I. Pigment Black 27); carbon black (C.I. Pigment Black 7);
color pigments:
chromium oxide, chromium oxide hydrate green; chrome green (C.I. Pigment Green 48); cobalt green (C.I. Pigment Green 50); ultramarine green;
cobalt blue (C.I. Pigment Blue 28 and 36); ultramarine blue; iron blue (C.I. Pigment Blue 27); manganese blue;
ultramarine violet; cobalt violet, manganese violet;
iron oxide red (C.I. Pigment Red 101); cadmium sulfoselenide (C.I. Pigment Red 108); molybdate red (C.I. Pigment Red 104); ultramarine red;
iron oxide brown, mixed brown, spinel and corundum phases (C.I. Pigment Brown 24, 29 and 31), chrome orange;
iron oxide yellow (C.I. Pigment Yellow 42); nickel titanium yellow (C.I. Pigment Yellow 53; C.I. Pigment Yellow 157 and 164); chrome titanium yellow; cadmium sulfide and cadmium zinc sulfide (C.I. Pigment Yellow 37 and 35); chrome yellow (C.I. Pigment Yellow 34), zinc yellow, alkaline earth metal chromates; Naples yellow; bismuth vanadate (C.I. Pigment Yellow 184);
interference pigments:
metallic effect pigments based on coated metal platelets; pearl luster pigments based on mica platelets coated with metal oxide; liquid crystal pigments.
Preferred pigments in this context are monoazo pigments (especially laked BONS pigments, naphthol AS pigments), disazo pigments (especially diaryl yellow pigments, bisacetoacetanilide pigments, disazopyrazolone pigments), quinophthalone pigments, phthalocyanine pigments, triarylcarbonium pigments (alkali blue pigments, dye salts with complex anions) and carbon black.
The pigment present in the pigment preparations of the invention should be very finely divided. It is preferred for 95%, preferably 99%, of the pigment particles to have a particle size ≦1 &mgr;m.
The pigment particles can have different shapes and accordingly influence the flow behavior of the pigment preparations. Nonisometric pigment particles generally lead to higher flow viscosities and frequently to an absence of Newtonian flow characteristics, whereas isometric pigment particles generally produce less viscous preparations at the same pigment concentration and usually exhibit Newtonian flow characteristics.
The pigment preparations of the invention generally comprise from 0.1 to 20% by weight, preferably from 0.2 to 10% by weight, of pigment (A).
Component (B) of the pigment preparations of the invention is a water-soluble dispersant based on one or more arylsulfonic acid/formaldehyde condensation products (B1) or one or more water-soluble alkoxylated phenols (B2).
Preferred dispersants (B1) are condensation products having a

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