DE19938471A1 - Dye preparation for ink jet printing, especially on paper, contains dispersed or dissolved dye, dispersant if required, a low-molecular weight poly-tetrahydrofuran, optionally with water-soluble- or -miscible solvent, and water - Google Patents

Abstract

Dye preparations containing a low-mol. wt. poly-tetrahydrofuran (C1), optionally in combination with hardly-volatile, water-soluble or water-miscible organic solvent(s) (C2), in addition to a dispersed dye (A1) or dissolved dye (A2), a dispersant (B) if (A1) is present, and water (D). An Independent claim is also included for a method for printing flat or 3-dimensional substrates by the ink jet technique, in which dye preparations as described above are printed onto the substrate and the print is then fixed if required.

Description

The present invention relates to new colorant preparations which

• A) at least one dispersed (A1) or dissolved (A2) color medium,
• B) in the case of a colorant (A1), a dispersant,
• C) a low molecular weight polytetrahydrofuran (C1), desired if mixed with one or more difficult to evaporate, water-soluble or water-miscible organic Solvents (C2) and
• D) water

included as essential components.

The invention further relates to the use of these colors preparations as inks for the ink jet process and a process for printing flat or three-dimensional designed substrates in the ink-jet process, in which these Colorant preparations are used.

To the inks used in the ink jet process (ink jet printing drive like Thermal Ink Jet, Piezo Ink Jet, Continuous Ink Jet, Valve Jet) are used to meet a number of requirements put: You need suitable viscosity and upper for printing have surface tension, they must be stable in storage, d. that is, they should not coagulate or flocculate, and they must not lead to blockage of the printer nozzle, which is particularly the case with dis pergiert, ie containing undissolved colorant particles Inks can be problematic. The requirements for the bearings The stability of these inks also means that the dis do not settle the colorant particles. Finally have to In the case of the continuous ink jet, the inks are stable against the ink of conductive salts and none when the ion content is increased Show tendency to flocculate. In addition, the received Prints meet the color requirements, d. H. high glasses Show lance and depth of color, and good fastness properties, e.g. B. Rubbing fastness fastness, light fastness, water fastness and wet rub fastness point.  

Ink-jet inks containing pigment are known from WO-A-99/01516. which, however, differ from the present colorant preparations distinguish by component (C).

The object of the present invention was to provide new colorants Preparations to provide what advantageous application in Ink-jet processes can be found and especially good have writing and continuous writing behavior.

Accordingly, the colorant preparations defined at the outset found.

The colorant preparations according to the invention can essentially Chen insoluble, dispersed colorant (A1) (finely divided, organic or inorganic pigments or in water / solvents tel mixture insoluble dyes) or dissolved colorant (A2) (dyes soluble in the water / solvent mixture). The colorants according to the invention can of course also be added preparations also contain colorant mixtures, preferably however, there is only one colorant. Invention are preferred appropriate pigment-based colorant preparations.

The following are examples of suitable pigments (A1) the vat dyes due to the overlap with the organic pigments are listed.

Organic pigments:
Monoazo pigments:
CI Pigment Brown 25;
CI Pigment Orange 5, 13, 36 and 67;
CI 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, 112, 146, 170, 184, 210, 245 and 251;
CI Pigment Yellow 1, 3, 73, 74, 65, 97, 151 and 183;
Disazo pigments:
CI Pigment Orange 16, 34 and 44;
CI Pigment Red 144, 166, 214 and 242;
CI Pigment Yellow 12, 13, 14, 16, 17, 81, 83, 106, 113, 126, 127, 155, 174, 176 and 188;
Anthanthrone pigments:
CI Pigment Red 168 (CI Vat Orange 3);
Anthraquinone pigments:
CI Pigment Yellow 147 and 177;
CI Pigment Violet 31;
Anthrapyrimidine Pigments:
CI Pigment Yellow 108 (CI Vat Yellow 20);
Quinacridone pigments:
CI Pigment Red 122, 202 and 206;
CI Pigment Violet 19;
Quinophthalone pigments:
CI Pigment Yellow 138;
Dioxazine pigments:
CI Pigment Violet 23 and 37;
Flavanthrone Pigments:
CI Pigment Yellow 24 (CI Vat Yellow 1);
Indanthrone Pigments:
CI Pigment Blue 60 (CI Vat Blue 4) and 64 (CI Vat Blue 6);
Isoindoline pigments:
CI Pigment Orange 69;
CI Pigment Red 260;
CI Pigment Yellow 139 and 185;
Isoindolinone pigments:
CI Pigment Orange 61;
CI Pigment Red 257 and 260;
CI Pigment Yellow 109, 110, 173 and 185;
Isoviolanthrone Pigments:
CI Pigment Violet 31 (CI Vat Violet 1);
Metal complex pigments:
CI Pigment Yellow 117, 150 and 153;
CI Pigment Green 8;
Perinone pigments:
CI Pigment Orange 43 (CI Vat Orange 7);
CI Pigment Red 194 (CI Vat Red 15);
Perylene pigments:
CI Pigment Black 31 and 32;
CI Pigment Red 123, 149, 178, 179 (CI Vat Red 23), 190 (CI Vat Red 29) and 224;
CI Pigment Violet 29;
Phthalocyanine Pigments:
CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6 and 16;
CI Pigment Green 7 and 36;
Pyranthrone pigments:
CI Pigment Orange 51;
CI Pigment Red 216 (CI Vat Orange 4);
Thioindigo pigments:
CI Pigment Red 88 and 181 (CI Vat Red 1);
CI Pigment Violet 38 (CI Vat Violet 3);
Triaryl carbonium pigments:
CI Pigment Blue 1, 61 and 62;
CI Pigment Green 1;
CI Pigment Red 81, 81: 1 and 169;
CI Pigment Violet 1, 2, 3 and 27
CI Pigment Black 1 (aniline black);
CI Pigment Yellow 101 (Aldazine Yellow);
CI Pigment Brown 22;

Vat dyes (except those already mentioned above):
CI Vat Yellow 2, 3, 4, 5, 9, 10, 12, 22, 26, 33, 37, 46, 48, 49 and 50;
CI Vat Orange 1, 2, 5, 9, 11, 13, 15, 19, 26, 29, 30 and 31;
CI Vat Red 2, 10, 12, 13, 14, 16, 19, 21, 31, 32, 37, 41, 51, 52 and 61;
CI Vat Violet 2, 9, 13, 14, 15, 17 and 21;
CI Vat Blue 1 (CI 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;
CI Vat Green 1, 2, 3, 5, 7, 8, 9, 13, 14, 17, 26, 29, 30, 31, 32, 33, 40, 42, 43, 44 and 49;
CI 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;
CI 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 (CI Pigment White 6), zinc white, colored zinc oxide; Zinc sulfide, lithopone; Lead white;
Black pigments:
Iron oxide black (CI Pigment Black 11), iron-manganese black, spinel black (CI Pigment Black 27); Carbon black (CI Pigment Black 7);
Colored pigments:
Chromium oxide, chromium oxide hydrate green; Chrome green (CI Pigment Green 48); Cobalt green (CI Pigment Green 50); Ultramarine green;
Cobalt blue (CI Pigment Blue 28 and 36); Ultramarine blue; Iron blue (CI Pigment Blue 27); Manganese blue;
Ultramarine violet; Cobalt and manganese purple;
Iron oxide red (CI Pigment Red 101); Cadmium sulfoselenide (CI Pigment Red 108); Molybdate red (CI Pigment Red 104); Ultra marine red;
Iron oxide brown, mixed brown, spinel and corundum phases (CI Pigment Brown 24, 29 and 31), chrome orange;
Iron oxide yellow (CI Pigment Yellow 42); Nickel titanium yellow (CI Pigment Yellow 53; CI Pigment Yellow 157 and 164); Chrome titanium yellow; Cadmium sulfide and cadmium zinc sulfide (CI Pigment Yellow 37 and 35); Chrome yellow (CI Pigment Yellow 34), zinc yellow, alkaline earth chromates; Naples yellow; Bismuth vanadate (CI Pigment Yellow 184);
Interference pigments:
Metallic effect pigments based on coated metal flakes; Pearlescent pigments based on metal oxide coated mica flakes; Liquid crystal pigments.

Monoazo pigments (in particular lacquered BONS pigments, naphthol AS pigments), disazo pigments (especially diaryl yellow pigments, bisacetoacetic acid acetanilide pigments, disazopyrazolone pigments), quinacridone pigments, quinoph thalon pigments, perinone pigments, phthalocyanine pigments, triaryl carbonium pigments (alkali blue pigments, lacquered rhodamines, color substance salts with complex anions), isoindoline pigments and carbon black call.

The following are examples of particularly preferred pigments:
CI Pigment Yellow 138, CI Pigment Red 122, CI Pigment Violet 19, CI Pigment Blue 15: 3 and 15: 4, CI Pigment Black 7, CI Pigment Orange 5, 38 and 43 and CI Pigment Green 7.

These pigments can be advantageous for creating ink jet tin tensets based on the colorant preparations according to the invention be used. The content of the individual inks in the respective pigments is adapted to the respective requirements (e.g. Trichromatic).

The following pigment combinations are particularly recommended:
CI Pigment Yellow 138, CI Pigment Violet 19, CI Pigment Blue 15: 3 and CI Pigment Black 7;
CI Pigment Yellow 138, CI Pigment Red 122, CI Pigment Blue 15: 3 or 15: 4 and CI Pigment Black 7;
CI Pigment Yellow 138, CT Pigment Violet 19, CI Pigment Blue 15: 3, CI Pigment Black 7, CI Pigment Orange 43 and CI Pigment Green 7;
CI Pigment Yellow 138, CI Pigment Red 122, CI Pigment Blue 15: 3 or 15: 4, CI Pigment Black 7, CI Pigment Orange 5 and CI Pigment Green 7;
CI Pigment Yellow 138, CI Pigment Red 122, CI Pigment Blue 15: 3 or 15: 4, CI Pigment Black 7, CI Pigment Orange 38 and CI Pigment Green 7;
CI Pigment Yellow 138, CI Pigment Red 122, CI Pigment Blue 15: 3 or 15: 4, CI Pigment Black 7, CI Pigment Orange 43 and CI Pigment Green 7.

As dyes (A1) in the water / solvent mixture in we are insoluble, are suitable in addition to those already mentioned Vat dyes in particular azo, anthraquinone, chino phthalone, benzodifuran, methine and azamethine dyes, the are free of acidic or ionic groups.

Examples of suitable dyes (A1) are:
CI Disperse Yellow 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 11: 1, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 , 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47 , 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72 , 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97 , 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 179 , 180, 181, 182, 183, 184, 184: 1, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217 , 218, 219, 220, 221, 222, 223, 224, 225, 226, 227 and 228;
CI Disperse Orange 1, 2, 3, 3: 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 , 23, 24, 25, 25: 1, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 41: 1, 42, 43 , 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68 , 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 126, 127 , 128, 129, 130, 131, 136, 137, 138, 139, 140, 141, 142, 143, 145, 146, 147 and 148;
CI Disperse Red 1, 2, 3, 4, 5, 5: 1, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 , 23, 24, 25, 26, 27, 28, 29, 30, 30: 1, 31, 32, 33, 34, 35, 36, 38, 39, 40, 41, 43, 43: 1, 46, 48 , 50, 51, 52, 53, 54, 55, 55: 1, 56, 58, 59, 60, 61, 63, 65, 66, 69, 70, 72, 73, 74, 75, 76, 77, 79 , 80, 81, 82, 84, 85, 86, 86: 1, 87, 88, 89, 90, 91, 92, 93, 94, 96, 97, 98, 100, 102, 103, 104, 105, 106 , 107, 108, 109, 110, 111, 112, 113, 115, 116, 117, 118, 120, 121, 122, 123, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134 , 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 151: 1, 152, 153, 154, 155, 156, 157 , 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 167: 1, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180 , 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 190: 1, 191, 191: 1, 192, 193, 194, 195, 211, 223, 273, 274, 275, 276 , 277, 278, 279, 280, 281, 302: 1, 305, 306, 307, 308, 309, 310, 311, 312, 313, 314, 315, 316, 317, 318, 319, 320, 32 1, 322, 323, 324, 325, 326, 327, 328, 329, 330, 331, 332, 333, 334, 335, 336, 338, 339, 340, 341, 342, 343, 344, 346, 347, 348, 349, 356 and 367;
CI Disperse Violet 1, 2, 3, 4, 4: 1, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 , 23, 24, 25, 26, 27, 28, 29, 31, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49 , 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 70, 81, 86, 87, 88, 89, 91, 92, 93, 94, 96 and 97;
CI Disperse Blue 1, 1: 1, 2, 3, 3: 1, 4, 5, 6, 7, 7: 1, 8, 9, 10, 11, 12, 13, 13: 1, 14, 15, 16 , 17, 18, 19, 20, 21, 22, 23, 23: 1, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 38, 39, 40 , 42, 43, 44, 45, 47, 48, 49, 51, 52, 53, 54, 55, 56, 58, 60, 60: 1, 61, 62, 63, 64, 64: 1, 65, 66 , 68, 70, 72, 73, 75, 76, 77, 79, 80, 81, 81: 1, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94 , 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 111, 112, 113, 114, 115, 116, 117, 118, 119, 121 , 122, 123, 124, 125, 126, 127, 128, 130, 131, 132, 133, 134, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148 , 149, 150, 151, 152, 153, 154, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 165: 2, 166, 167, 168, 169, 170, 171, 172 , 173, 174, 175, 195, 281, 282, 283, 283: 1, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 316, 317, 318, 319, 320 , 321, 322, 323, 324, 325, 326, 327, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 344, 345 , 3rd 46, 347 and 349;
CI Disperse Green 1, 2, 5, 6 and 9;
CI Disperse Brown 1, 2, 3, 4, 4: 1, 5, 7, 8, 9, 10, 11, 18, 19, 20 and 21;
CI Disperse Black 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 20, 22, 24, 25, 26, 27, 28, 29, 29: 1 , 30, 31, 32, 33, 34 and 36;
CI Solvent Yellow 2, 3, 7, 12, 13, 14, 16, 18, 19, 21, 25, 25: 1, 27, 28, 29, 30, 33, 34, 36, 42, 43, 44, 47 , 56, 62, 72, 73, 77, 79, 81, 82, 83, 83: 1, 88, 89, 90, 93, 94, 96, 98, 104, 107, 114, 116, 117, 124, 130 , 131, 133, 135, 141, 143, 144, 145, 146, 157, 160: 1, 161, 162, 163, 167, 169, 172, 173, 176, 179, 180, 181, 182, 183, 184 , 185, 186, 187, 189, 190 and 191;
CI Solvent Orange 1, 2, 3, 4, 5, 7, 11, 14, 20, 23, 25, 31A, 40: 1, 41, 45, 54, 56, 58, 60, 62, 63, 70, 75 , 77, 80, 81, 86, 99, 102, 103, 105, 106, 107, 108, 109, 110, 111, 112 and 113;
CI Solvent Red 1, 2, 3, 4, 8, 16, 17, 18, 19, 23, 24, 25, 26, 27, 30, 33, 35, 41, 42, 45, 48, 49, 52, 68 , 69, 72, 73, 83: 1, 84: 1, 89, 90, 90: 1, 91, 92, 106, 109, 111, 118, 119, 122, 124, 125, 127, 130, 132, 135 , 141, 143, 145, 146, 149, 150, 151, 155, 160, 161, 164, 164: 1, 165, 166, 168, 169, 172, 175, 179, 180, 181, 182, 195, 196 , 197, 198, 207, 208, 210, 212, 214, 215, 218, 222, 223, 225, 227, 229, 230, 233, 234, 235, 236, 238, 239, 240, 241, 242, 243 , 244, 245, 247 and 248,
CI Solvent Violet 2, 8, 9, 11, 13, 14, 21, 21: 1, 26, 31, 36, 37, 38, 45, 46, 47, 48, 49, 50, 51, 55, 56, 57 , 58, 59, 60 and 61;
CI Solvent Blue 2, 3, 4, 5, 7, 18, 25, 26, 35, 36, 37, 38, 43, 44, 45, 48, 51, 58, 59, 59: 1, 63, 64, 67 , 68, 69, 70, 78, 79, 83, 94, 97, 98, 99, 100, 101, 102, 104, 105, 111, 112, 122, 124, 128, 129, 132, 136, 137, 138 , 139 and 143,
CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34 and 35;
CI Solvent Brown 1, 3, 4, 5, 12, 20, 22, 28, 38, 41, 42, 43, 44, 52, 53, 59, 60, 61, 62 and 63;
CI Solvent Black 3, 5, 5: 2, 7, 13, 22, 22: 1, 26, 27, 28, 29, 34, 35, 43, 45, 46, 48, 49 and 50.

In addition, substituted benzodifuranone dyes are suitable, the main body of the formula

corresponds. Such dyes can be on one or both phenyl wrestle be substituted. Halogen, Al. Come as substituents kyl, which may be due to non-adjacent oxygen atoms is interrupted, alkoxy, whose alkyl radical by oxygen atoms can be interrupted and can also be substituted, Hydroxy, optionally substituted amino, cyano, nitro and Alkoxycarbonyl into consideration.

Dyes of the following formulas are also suitable:

Further examples of insoluble dyes (A1) are in the WO-A-97/46623, 98/24850 and 99/29783.

The undissolved, dispersed colorant (A1) should be as possible be finely divided. Preferably 95%, particularly preferably 99%, the colorant particles (A1) a particle size ≦ 1 micron, preferred ≦ 0.5 µm.

As dyes (A2), which are soluble in the water / solvent mixture are particularly suitable arylmethane, azo, methine, rhod amine and metal complex dyes, the acidic or ionic group pen included.

Examples of suitable dyes (A2) are:
CI Basic Yellow 2, 37, 78, 94, 96, 97, 98, 102 and 111;
CI Basic Orange 2, 60, 62 and 63;
CI Basic Red 1, 14, 49, 108 and 111;
CI Basic Violet 1, 3, 4, 10, 11, 49 and 50;
CI Basic Blue 26, 152, 157, 158 and 161;
CI Basic Green 1 and 4;
CI Basic Brown 1;
CI Acid Orange 7 and 8;
CI Acid Blue 9;
CI Direct Yellow 4, 5, 11, 15, 127, 131 and 147;
CI Direct Red 239 and 254;
CI Direct Blue 161, 199, 279 and 281;
CI Reactive Red 120.

The colorant preparations according to the invention contain in the Rule 0.01 to 20 wt .-%, preferably 0.1 to 10 wt .-%, particularly preferably 0.2 to 60% by weight of colorant (A), with colorant (A1) Amounts in the range of 0.2 to 6% by weight and for colorants (A2) Amounts in the range from 1 to 10% by weight are particularly suitable are.

The colorant preparations according to the invention are based on unge dissolved colorants (A1), then they contain a dispersant (B). In the case of dissolved colorants (A2), the component is (B) of course not necessary.

In principle, all of them are suitable as component (B) for aqueous Sy known dispersants.

Water-soluble dispersants on the Base of one or more water soluble oxyalkylated phenols (B1), one or more arylsulfonic acid-formaldehyde condensates  tion products (B2) or one or more condensation products of an at least difunctional isocyanate, each with one iso compounds bearing cyanate-reactive groups (B3).

The dispersants (B1) are oxyalkylated phenols of the formula I or II

in which
a 0 to 125 on average,
b on average 37 to 250, where in the case of b <37 the ratio b: a is at least 1: 1, and
d is 0 or 1, or mixtures thereof are preferred.

The products of the formula I and II can by reacting the phenol derivatives of the formula III or IV

with propylene oxide and subsequent reaction of the adduct with Ethylene oxide or by reacting III and / or IV with ethylene oxide can be obtained. If necessary, the adducts with Chlorosulfonic acid or sulfur trioxide completely or partially converted to sulfuric acid half-esters and the half-esters obtained neutralized with alkaline agents.

The phenols of the formula III and IV can be obtained by reacting phenol or 2,2- (p, p'-bishydroxydiphenyl) propane with 3 or 4 mol of styrene in the presence of acid as a catalyst. The phenols III and IV are first reacted by known processes with ethylene oxide or only with ethylene oxide in the presence of acidic or alkaline catalysts to give the corresponding oxyalkylation products I and II with d = 0. The oxyalkylation can e.g. B. by the method described in US-A-2 979 528. For the case b <37 the quotient must be

his.

The sulfuric acid semiesters are obtained by reaction of the oxyalkylators products with chlorosulfonic acid or sulfur trioxide provides, the amount can be chosen so that all free Hydroxy groups or only a part is sulfated. In the latter Traps form mixtures of compounds of formula I and II, which contain free and sulfated hydroxy groups. Ver Use as dispersants in the implementation obtained half ester of sulfuric acid in water-soluble salts transferred. The alkali metal salts, e.g. B. the sodium or potassium salts. Here are in Two equivalents for chlorosulfonic acid, for sulfur trioxide an equivalent of basic compounds is required. As the latter is advantageously used in aqueous alkali metal  hydroxide. During neutralization, the temperature should not be 70 ° C exceed. The salts obtained can be in the form of aqueous Solutions or as such isolated and in solid form be used.

Dispersants (B1) in which a is 0 to on average are preferred 2.5, b is 37 to 250 on average and d is 0 to 0.5 on average. Be dispersants (B1) in which a is 0 to. are particularly preferred on average 2.5, b on average 50 to 100 and d on average 0.5.

The dispersants (B1) are known and z. B. in the US-A-4 218 218.

The condensation products (B2) are aromatic by sulfonation contain compounds such as naphthalene itself or naphthalene tender mixtures and subsequent condensation of the formed Arylsulfonic acids available with formaldehyde.

As a starting product for the production of arylsulfonic acids comes z. B. a mixture of such aromatic compounds in Be tracht by thermal fission of a naphthenic back base oil and fractionation of the fission products are available. The naphthenic residue oils fall, for example Cracking from light petrol and are also considered high-boiling called aromatic hydrocarbon oils. The naphthenic Residual oil is preferably at a temperature of 1400 to Thermally split at 1700 ° C. The fission products then become one fractional distillation fed. The at normal pressure (1013 mbar) from 100 to 120 ° C passing fraction is collected and fed to the sulfonation as an aromatic compound. A such fraction is used in the known acetylene oil quench process usually obtained as a by-product (Ullmann's Encyclopedia of Industrial Chemistry, VCH Verlagsgesellschaft mbH, Weinheim, 1985, Volume A1, pages 107 to 112).

This aromatic fraction consists of a mixture of many aromatic substances, the structure and amount of which can practically not be determined in detail. The following aryl compounds are the main representatives of this aromatic fraction:

The aromatics fraction also contains identified stocks share the following arylver in amounts of 0.1 to about 2% by weight bindings: fluorene, indane, methylstyrene, phenanthrene, methylin dan, dimethylnaphthalene, ethylnaphthalene, xylenes, tetralin, Styrene, methylethylbenzene, anthracene, fluoranthrene, pyrene, acet naphthylene and toluene.

Particularly suitable arylsulfonic acids usually contain α- and β-naphthalenesulfonic acids, the ratio of α to β-isomers usually 20: 1 to 1: 8, in particular 10: 1 to 1: 5 is.

The condensation products show when using the above. Aromatic fraction prefers a sulfonic acid group content of a maximum of 40% by weight.

The dispersant (B2) can be prepared in the presence of aromatic or long-chain aliphatic carboxylic acids, the Salts, anhydrides or mixtures of these compounds be taken.

Examples of suitable aromatic carboxylic acids or their deri vate are naphthalene carboxylic acid, naphthalic acid, terephthalic acid, Isophthalic acid, benzoic acid, trimellitic acid, phenylacetic acid, Phenoxyacetic acid, salicylic acid, p-hydroxybenzoic acid, diphenyl acetic acid, m-hydroxybenzoic acid, benzene tetracarboxylic acid or Acid anhydrides such as phthalic anhydride, trimellitic anhydride, Benzene-1,2,4,5-tetracarboxylic acid dianhydride or naphthalic acid anhydride.

Suitable long-chain aliphatic carboxylic acids are in particular saturated or olefinically unsaturated, linear or branched aliphatic monocarboxylic acids with 8 to 22, preferably 8 to 18 carbon atoms, natural or synthetic, for example higher fatty acids such as caprylic acid, capric acid, Lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, Linoleic acid or linolenic acid or synthetically produced Carboxylic acids such as 2-ethylhexanoic acid, isononanoic acid or isotri decanoic acid.  

The salts of the carboxylic acids mentioned are the alkali, Ammonium or alkaline earth metal salts, for example by neutralizing these carboxylic acids with sodium hydroxide solution, potassium lye, lithium hydroxide, soda, magnesium carbonate, calcium oxide, Calcium hydroxide, ammonia or alkanolamines such as ethanolamine, Diethanolamine or triethanolamine are available.

Sodium benzoate, sodium phenylacetate and sodium are preferred salicylate, sodium 4-hydroxybenzoate, sodium terephthalate, Sodium 2-hydroxy-3-naphthalene carboxylate, naphthalene-1-carbon acid, phthalic anhydride or benzoic acid.

In this case, the most suitable dispersants (B2) are such mixtures, the 50 to 97 wt .-%, in particular 70 to 95% by weight, arylsulfonic acid-formaldehyde condensation products and 3 to 50 wt .-%, in particular 5 to 30 wt .-%, aromatic or long chain aliphatic carboxylic acids, their salts or their Contain anhydrides or mixtures thereof.

One can advantageously in the production of arylsulfonic acid Formaldehyde condensation products (B2) also from pure naphthalene (Purity usually <95%).

The condensation is generally 0.5 to 1.5 mol, preferably 0.7 to 1 mol, formaldehyde per mol of naphthalene set.

The sulfonic acid group content of these condensation products is expediently at about 40 to 50% by weight.

The dispersants (B2) are known and z. B. in the US-A-5 186 846, DE-A-11 37 005 or EP-A-380 778 described.

The dispersants (B3) are condensation products of min least difunctional isocyanates, which act as a linking point serve with a polymeric compound attached to one chain end is terminated with an isocyanate-reactive group and which too dispersing solid particles with the dispersion medium inert (hereinafter called "stabilizer block"), and a (homo- or co-) polymer of a nitrogen-containing monomer or a phosphonic acid ester, each via an isocycanat reactive group and adhere to the solid to be dispersed attach material particles (in the following "anchor group block" ge called).  

This is the linking of the stabilizer block and anchor group block effecting isocyanate is a diisocyanate or a high function bright polyisocyanate with an average NCO functionality of 2.0 to 4.5.

The diisocyanates can be aromatic or aliphatic before aliphatic diisocyanates such as tetramethylene diisocyanate Hexamethylene diisocyanate, octamethylene diisocyanate, decamethylene di isocyanate, dodecamethylene diisocyanate, tetradecamethylene diiso cyanate, trimethylhexane diisocyanate, tetramethylhexane diisocyanate, 1,4-, 1,3- or 1,2-diisocyanatocyclohexane, 4,4'-di (isocyanato cyclohexyl) methane, 1-isocyanato-3,3,5-trimethyl-5- (isocyanato methyl) cyclohexane (isophorone diisocyanate) and 2,4- and 2,6-diiso cyanato-1-methylcyclohexane, where hexamethylene diisocyanate and Isophorone diisocyanate are particularly preferred.

The higher functional polyisocyanates can also be aromatic or aliphatic. Here too, the aliphatic polyisocyanates are preferred, especially those with an average NCO functionality of 1.7 to 5, in particular about 3. The following groups are examples:

• a) Isocyanurate group-containing polyisocyanates from aliphati and / or cycloaliphatic diisocyanates. Especially the corresponding isocyanato isocya are preferred nurates based on hexamethylene diisocyanate and isophorone diisocyanate. These isocyanurates are in particular special about simple tris-isocyanatoalkyl or triisocyanato cycloalkyl isocyanurates, which cyclic trimers of Diiso represent cyanates, or mixtures with their higher, more as homologues containing an isocyanurate ring. The Isocya NATO isocyanurates generally have an NCO content of 10 to 30 wt .-%, in particular 15 to 25 wt .-%, and a average NCO functionality from 2.6 to 4.5.
• b) uretdione diisocyanates with aliphatic and / or cycloalipha table-bound isocyanate groups, which are preferably from Derive hexamethylene diisocyanate or isophorone diisocyanate. Uretdione diisocyanates are cyclic dimers Risk products of diisocyanates.
• c) Biuret group-containing polyisocyanates with aliphatic ge bound isocyanate groups, especially tris (6-isocyanatohe xyl) biuret or its mixtures with its higher homologues. These biuret groups have polyisocyanates  generally an NCO content of 18 to 25 wt .-% and average NCO functionality from 3 to 4, 5.
• d) polyisocya containing urethane and / or allophanate groups nate with aliphatic or cycloaliphatic bound Isocya nat groups, such as those implemented by implementing shot amounts of hexamethylene diisocyanate or isopho rondiisocyanate with simple polyhydric alcohols, such as tri methylolpropane, glycerin, 1,2-dihydroxypropane or their Ge mix can be obtained. This urethane and / or allo Polyisocyanates containing phanate groups generally have NEN content of 12 to 20 wt .-% and an average NCO functionality from 2.5 to 3.
• e) Polyisocyanates containing oxadiazinetrione groups, preferably white of hexamethylene diisocyanate or isophorone diisocyanate derived. Such poly containing oxadiazinetrione groups Isocyanates can be produced from diisocyanate and carbon dioxide.
• f) Uretonimine-modified polyisocyanates.

The polymeric compound forming the stabilizer block is preferably a polymeric compound of the general formula V

R ¹ -M _n -XH V)

wherein
R ¹ for hydrogen, optionally branched C ₁ -C ₂₈ alkyl, optionally branched, optionally polyunsaturated C ₂ -C ₂₈ alkenyl, optionally branched, optionally polyunsaturated C ₂ -C ₂₈ alkynyl or the rest of a polymerization initiator or a chain regulator,
M represents identical or different polymerized units of monomers selected from α, unsaturated mono- or dicarboxylic acids, optionally substituted with hydroxy, C ₁ -C ₆ alkoxy, polyalkyleneoxy or halogen-mono- ethylenically β-or polysubstituted C ₁ -C ₂₀ - ( Cyclo) alkyl or C ₇ -C ₂₀ aralkyl esters, amides, nitriles or anhydrides of α, β-ethylenically unsaturated mono- or dicarboxylic acids, vinyl or allyl esters of aliphatic or aromatic carboxylic acids, vinyl or allyl ethers, ethylenically unsaturated sulfonic acids or Sul fonic acid derivatives, optionally halogenated ethylenically unsaturated aliphatic C ₂ -C ₂₀ hydrocarbons, aromatic ethylenically unsaturated compounds or compounds polymerizable to polyphosphacenes, or for

in which R ² , R ³ , R ⁴ and R ⁵ independently of one another are H, C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, -CH ₂ -Cl or -CH ₂ -OH, and R ⁶ , R ⁷ and R ⁸ independently of one another represent a C ₂ -C ₂₀ alkylene, arylene or aralkylene group,
n stands for an integer between 0 and 10,000, where n is preferably ≧ 2, in particular ≧ 3 and particularly preferably 30 to 1000, and
X represents COO, O, S or NR ⁹ , wherein R ^{9 represents} H or a C ₁ -C ₆ alkyl group.

VC ₁ -C ₉ -alkyl (meth) acrylates are preferably used to construct the polymeric compound. One or more C ₁ -C ₄ -alkyl methacrylates, in particular methyl methacrylate and / or butyl methacrylate, are particularly preferably polymerized. The isocyanate-reactive group XH is preferably a hydroxyl group which can be introduced terminally into the polyacrylate with the aid of initiators which give a hydroxyl radical on decomposition and / or with the aid of chain regulators which contain a hydroxyl group.

Very particularly preferred as the polymeric compound V are mono- (usually C ₁ -C ₁₈ -, preferably C ₁ -C ₄ -) alkyl ethers of poly (in particular C ₂ -C ₄ -) alkylene glycols which, for. B. can be obtained by reacting an alkanol with alkene oxides, such as ethylene oxide, propylene oxide and butylene oxide, or epichlorohydrin. Particularly suitable are 5 to 10,000, preferably 5 to 80 mol of ethylene oxide and / or propylene oxide alkoxylated C ₁ -C ₁₈ - (in particular C ₁ -C ₄ -) alkanols, polyethylene glycol monomethyl ether being very particularly suitable.

The weight average molecular weight of the stabilizer block be preferably carries about 250 to 100,000, especially about 500 to 7000.

An embodiment suitable for building up the dispersant (B3) The shape of the anchor group block is based on homo- or copolymers seed of one or more monomers from the group of the N-Vinyla mide, N-vinyl lactams and vinyl or allyl substituted stick containing heterocycles. Examples of particularly suitable ones Monomers are N-vinyl pyrrolidone, N-vinyl pyridine, N-vinyl caprolac tam, N-vinylimidazole and N-vinylformamide, where N-vinylpyrrolidone is preferred. The homo- or copolymer preferably has one K value from 10 to 100, in particular 10 to 30. The Terminie tion by a hydroxyl group as an isocyanate-reactive group by performing the polymerization in water or a low ren alcohol such as isopropanol or by polymerization in counter were a corresponding chain regulator and / or initiator be enough.

Another embodiment of the anchor group block suitable for building up the dispersant (B3) are phosphonic acid esters of the formula VI

in the
R ¹⁰ and R ¹¹ independently of one another are C ₁ -C ₄ alkyl, in particular R ¹⁰ = R ^{11 are} methyl or ethyl;
Q represents NR _(2-p) or CR _(3-p) (R = H or C ₁ -C ₈ alkyl);
R ¹² and R ¹³ independently of one another represent a chemical bond or C ₁ -C ₁₀ alkylene which is optionally substituted by C ₁ -C ₈ alkyl or aryl, which is optionally by O, NR, CO, COO, OCO, CONR or NRCO can be interrupted;
p represents 1 or 2; and
Y is COO, O, S or NR ¹⁴ , where R ^{14 is} H or a C ₁ -C ₆ alkyl group.

Preferred examples of these phosphonic acid esters are N, N- Bis (hydroxyethyl) aminomethylphosphonic acid diethyl ester, dimethyl and diethyl ester of 3-hydroxymethylamino-3-oxopropylphosphon acid, 3-aminopropylphosphonic acid, 1-aminopropylphosphonic acid, 2-aminooctylphosphonic acid, 1-aminooctylphosphonic acid, 1-aminobu tylphosphonic acid, hydroxymethylphosphonic acid and 1-hydroxyethyl phosphonic acid.

The implementation of the di- or polyisocyanate with the stabilizer block and the anchor group block can be two-stage or in one One-pot reaction take place. The conversion is preferably carried out in each case but in two stages, with the di- or poly Isocyanate is implemented with the stabilizer block. The implementation can be carried out in bulk or in a solvent, the Reaction in a solvent such as acetone, THF, toluene, dio xan, is preferred. If the stabilizer block by Polymerisa tion of an ethylenically unsaturated compound the stabilizer block can be implemented with the di- or polyisocyanate advantageously in the same solvent as that radical polymerization can be carried out. The reaction can without catalyst or preferably in the presence of a catalyze catalysts, such as a tertiary amine, especially triethylamine, or a metal salt, in particular tin octoate or lead octoate, or an organometallic compound such as dibutyltin dilaurate or titanium tetramethylate. The implementation will generally at a temperature from room temperature to 125 ° C, in particular 40 to 90 ° C, carried out.

Further details on the dispersants (B3) are in the older German patent application 198 42 952.5 described.

The colorant preparations according to the invention have in the case of an undissolved colorant (A1) usually has a content of 0.1 to 25% by weight, preferably from 0.5 to 10% by weight Dispersant (B).

The colorants according to the invention contain as component (C) preparations organic solvent. Low molecular weight poly tetrahydrofuran (C1) is an essential component of the component (C), it can be used alone or preferably in a mixture with one or several difficult to evaporate, soluble in water or with water miscible organic solvents (C2) are used.

The polytetrahydrofuran (C1) used according to the invention usually has an average molecular weight M _w of 150 to 500 g / mol, preferably from 200 to 300 g / mol and particularly preferably of about 250 g / mol (corresponding to a molecular weight distribution of 225 to 275 g / mol; poly-THF 250, BASF).

The polytetrahydrofuran (C1) can in a known manner via cat ionic polymerization of tetrahydrofuran. This creates linear polytetramethylene glycols.

If the polytetrahydrofuran (C1) mixed with other organi The solvents (C2) are present, for this purpose according to vaporisable (i.e. usually a boiling point < 100 ° C) and thus a water-retaining effect sedentary organic solvents used, which dissolve in water Lich or miscible with water.

Polyvalent alcohols are suitable as solvents (C2) before moves unbranched and branched polyhydric alcohols with 3 to 8, in particular 3 to 6, carbon atoms, such as 1,2- and 1,3-propylene glycol, glycerin, erythritol, pentaerythritol, pentites such as arabite, adonite and xylitol and hexites such as sorbitol, mannitol and Dulcite.

Other suitable solvents (C2) are polyethylene and poly propylene glycols, including the lower polymers (di-, tri- and tetramers), and their mono- (especially C ₁ -C ₆ -, especially C ₁ - C ₄ -) alkyl ether. Polyethylene and polypropylene glycols with average molecular weights from 100 to 1500, in particular from 100 to 800, are preferred. Examples include di-, tri- and tetraethylene glycol, diethylene glycol monomethyl, ethyl, propyl and butyl ether, triethylene glycol monomethyl , ethyl, propyl and butyl ether, di-, tri- and tetra-1,2- and -1,3-propylene glycol and di-, tri- and tetra-1,2- and 1,3- propylene glycol monomethyl, ethyl, propyl and butyl ether.

Also suitable as solvents (C2) are pyrrolidone and N- Alkylpyrrolidones, the alkyl chain of which is preferably 1 to 4, above al contains 1 to 2 carbon atoms. Examples of suitable ones Alkylpyrrolidones are N-methylpyrrolidone, N-ethylpyrrolidone and V- (2-hydroxyethyl) pyrrolidone.

Examples of particularly preferred solvents (C2) are 1,2- and 1,3-propylene glycol, glycerin, diethylene glycol, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, pyrrolidone, N-methylpyrrolidone and N- (2-hydroxyethyl) pyrrolidone.  

The polytetrahydrofuran (C1) can be mixed with one or more (e.g. two, three or four) solvents (C2) are mixed.

The colorant preparations according to the invention contain in the Rule 5 to 30 wt .-%, preferably 10 to 20 wt .-%, solvent component (C).

The weight ratio of (C2) to (C1) is preferably in the range range from 20: 1 to 1: 1. The colorants of the invention added Accordingly, preparations preferably contain 0.5 to 20 % By weight, in particular 1 to 10% by weight, of polytetrahydrofuran (C1) and 1 to 30% by weight, in particular 1 to 20% by weight, of solvent (C2).

Water is the main component (D) of the invention Colorant preparations. Its content is usually 50 up to 95% by weight, especially 60 to 80% by weight.

The colorants according to the invention can of course also be added preparations other aids, such as those for (aqueous) ink-jet inks and in the printing and coatings industry are common. May be mentioned for. B. Preservatives (such as 1,2-benzisothiazolin-3-one and its alkali metal salts, Glutardialdehyde and / or tetramethylolacetylene diurea), anti oxidants, degassers / defoamers (such as acetylenediols and ethoxy gated acetylenediols, usually 20 to 40 moles of ethylene oxide contain per mole of acetylenediol and at the same time also disperse act), means for regulating the viscosity, flow auxiliaries, wetting agents (e.g. wetting surfactants on the Basis of ethoxylated or propoxylated fat or oxo alcohols, propylene oxide / ethylene oxide block copolymers, ethoxylates of oleic acid or alkylphenols, alkylphenol ether sulfates, alkyl polyglycosides, alkylphosphonates, alkylphenylphosphonates, Al kylphosphates or alkylphenylphosphates), anti-settling agents, Gloss improver, lubricant, adhesion improver, skin prevention agents, matting agents, emulsifiers, stabilizers, Hydrophobing agents, light protection additives, grip improvers and an statistical agents. If these funds are part of the Invention are appropriate pigment preparations, their total amount is in usually ≦ 2 wt .-%, 1 wt .-%, based on the weight of the Zu preparation.

The colorant preparations according to the invention usually have a dynamic viscosity of 1 to 5 mm ² / sec, preferably 1 to 3 mm ² / sec.

The surface tension of the colorants according to the invention Preparations are usually 30 to 70 mN / m.

The pH of the colorant preparations according to the invention is generally 5 to 10, preferably 7 to 9.

The preparation of the colorant preparations based on undissolved colorant (A1) is advantageously carried out as follows:
The colorant (A1), for example in the form of a presscake containing water, is mixed together with the dispersant (B) in the presence of water and dispersed in a suitable apparatus. The resulting mixture is then ground in a mill in order to achieve the desired particle size distribution (generally ≦ 1 μm, preferably 0.5 μm). After the desired colorant concentration has been set by adding solvent (C), water and, if appropriate, other auxiliaries, filtration is carried out using a filter device with fine separation in the range from 1 to 0.5 μm.

As a starting material for preparations with dissolved dye (A2) are more concentrated dye solutions, e.g. B. 10 to 30 wt .-% liquid formulations of paper dyes, esp suitable. If necessary, these are desalted and filtered (e.g. nanofiltration) before the desired dye concentration tration is set.

The colorant preparations according to the invention can be advantageous in the method according to the invention for printing on flat or three-dimensional substrates in ink-jet Method is used, which is characterized in that one prints the colorant preparations on the substrate and then, if desired, fixed the pressure obtained.

In the ink jet process, the usually aqueous inks sprayed directly onto the substrate in small droplets. One under separates a continuous process in which the ink evenly pressed through a nozzle and through an electric Field, depending on the pattern to be printed, directed onto the substrate and an interrupted inkjet or "drop-on-demand" Process in which ink is ejected only where a colored point should be set. In the latter Ver will either drive over a piezoelectric crystal or a heated cannula (bubble or thermo-jet process) pressure exerted on the ink system and so an ink drop out hurled. Such procedures are in text. Chem. Color,  Volume 19 (8), pages 23 to 29, 1987, and Volume 21 (6), pages 27 to 32, 1989.

The colorants according to the invention are particularly suitable preparations as inks for the bubble jet process and for the Method using a piezoelectric crystal.

If you want to fix the pressure, you can use known ones Procedure and as described in WO-A-99/01516 and z. B. a binder, if desired in the form of a dispersion or Emulsion, apply to the printed substrate and harden or laminate a film.

The colorant preparations according to the invention can be printed on all types of substrate materials. As substrate materials such. B.

• - cellulose-containing materials such as paper, cardboard, cardboard, Wood and wood-based materials, which are also painted or otherwise can be coated
• - metallic materials such as foils, sheets or workpieces made of aluminum, iron, copper, silver, gold, zinc or Alloys of these metals that are painted or otherwise can be coated
• - silicate materials such as glass, porcelain and ceramics, which can also be coated
• - polymeric materials of any kind such as polystyrene, polyamides, Polyester, polyethylene, polypropylene, melamine resins, poly acrylates, polyacrylonitrile, polyurethanes, polycarbonates, poly vinyl chloride, polyvinyl alcohols, polyvinyl acetates, polyvinyl pyrrolidones and corresponding copolymers and block copolymers, biodegradable polymers and natural polymers such as Gelatin,
• - textile materials such as fibers, yarns, threads, knitwear, Woven goods, non-wovens and made-up goods made of polyester, modified polyester, polyester blend, cellulose materials like cotton, blended cotton, jute, Flax, hemp and ramie, viscose, wool, silk, polyamide, Polyamide blend, polyacrylonitrile, triacetate, acetate, Polycarbonate, polypropylene, polyvinyl chloride, polyester micro fibers and fiberglass fabrics,  
• - Leather, both natural leather and synthetic leather, as smooth, Nappa or suede,
• - Food and cosmetics

called.

The substrate material can be flat or three-dimensional be designed and with both full area and pictorial the colorant preparations according to the invention are printed.

The colorant preparations according to the invention are notable for Ink-jet inks with overall advantageous application properties above all, good writing behavior and good long-term writing behavior (cogation), and result in high quality print images, d. H. high brilliance and depth of color as well as high rubbing light, what Fastness to water and wet rubbing. They are particularly suitable for printing on coated and uncoated paper.

Examples I) Preparation of colorant preparations according to the invention example 1

15 g C.I. Pigment Yellow 138, 5 g 1,2-propylene glycol and 10 g egg dispersant (B1) based on an alkoxylated phenol, that described as dispersant 13 in US-A-4,218,218 is, 0.37 g 50 wt .-% aqueous solution of glutardialdehyde and 0.75 g 47% by weight aqueous solution of tetramethylolacetylenedi Urea was made with deionized water for a total weight of 100 g filled up and predispersed in a dissolver. Then the pH was adjusted to 8.5 with triethanolamine.

The mixture was then kept in a vertical position for so long Agitator ball mill with double grinding disc at 10 m / s circumference speed using 660 g of yttrium stabilized Zirconium oxide beads (diameter 0.3-0.4 mm) ground, up to 99% the pigment particles had a size of less than 1 μm.

For the final setting (4% by weight preparation), 37.5 g of meal well with 0.25 g of 50% by weight aqueous solution of glutardialdehyde, 0.22 g 47% by weight aqueous solution of tetramethylolacetylenedi urea, 10 g triethylene glycol monobutyl ether and 10 g poly tetrahydrofuran 250 (BASF) mixed with water to a level  filled up to a total weight of 100 g, mixed and passed through a sieve filtered to a pore size of 1 µm.

Examples 2 to 23

The pigment preparations of Examples 2 to 23 were made analogously Example 1 prepared. In Examples 20 and 21 and 22 and 23 However, a dispersant (B3) or (B3 ') based on a Reaction product of a triisocyanate with two each Compounds containing isocyanate-reactive group used (Example 1 or Example 4 of the older German patent application 198 42 952.5).

Dispersant B3

To a 35% by weight solution of polyethylene heated to 50 ° C. glycol monomethyl ether (MW 2000, 1 mol) in acetone was a han standard trifunctional isocyanate (Basonat® HB 100, BASF; 1 mol) and dibutyltin dilaurate as a catalyst. Ent was then the remaining isocyanate content OH-monofunctionalized polyvinylpyrrolidone (PVP, K value approximately 17) added. The reaction continued until no iso cyanate groups were more detectable.

Dispersant B3 '

To a 45% by weight solution of polyethylene heated to 50 ° C. glycol monomethyl ether (MW 2000, 1 mol) in tetrahydrofuran a commercially available trifunctional isocyanate (Basonat HB 100, BASF; 1 mol) and dibutyltin dilaurate as a catalyst. The remaining isocyanate content was then determined N, N-bis (hydroxyethyl) aminomethyldiethyl (phosphonate (Fyrol® 6, Akzo; about 2 moles; 50 wt .-% in tetrahydrofuran). The The reaction was continued until no more isocyanate groups to assign.

Further details on the pigment preparations obtained are summarized in Table 1. The percentages are in each case% by weight.

Example 24

2.5 g of an 80% by weight water-moist press cake of the dye of the formula VII

were dissolved in 87.5 g of water with stirring and with a filter MX 07 from Osmonics ultrafiltered. After adding 8 g 1,2-propylene glycol and 2 g of polytetrahydrofuran 250 was the Mix with a filter KS 80 from Seitz filtered to To separate suspended matter.

Examples 25 to 40

The dye preparations of Examples 25 to 40 were analogous Example 24 prepared.

Further details on the dye preparations obtained are summarized in Table 2. The percentages are in each case% by weight.

II) Testing of colorant preparations according to the invention

All colorant preparations showed when printing with commercial common inkjet printers on both coated and on uncoated paper excellent cover and through writing behavior and gave prints of high brilliance.

Claims (9)

1. Colorant preparations containing

• A) at least one dispersed (A1) or dissolved (A2) colorant,
• B) in the case of a colorant (A1), a dispersant,
• C) a low molecular weight polytetrahydrofuran (C1), if desired in a mixture with one or more hardly evaporable, water-soluble or water-miscible organic solvents (C2) and
• D) water

as essential components. 2. Colorant preparations according to claim 1, which, based in each case on the weight of the preparation,
0.01 to 20% by weight of component (A),
in the event that the colorant is essentially undissolved, 0.01 to 20% by weight of component (B),
0.1 to 40 wt .-% of component (C) and
at least 50% by weight of component (D)
contain. 3. Colorant preparations according to claim 1 or 2, which contain as component (C1) one or more polytetrahydrofurans with an average molecular weight M _w of 150 to 500 g / mol. 4. Colorant preparations according to claims 1 to 3, the 1st to 10 wt .-% of component (C1) and 1 to 20 wt .-% of Component (C2) included.   5. Colorant preparations according to claims 1 to 4, which as Component (C2) one or more solvents from the group polyhydric alcohols, polyethylene and polypropylene glycols as well as their monoalkyl ethers and pyrrolidone and N-alkylpyrroli done included. 6. Colorant preparations according to claims 1 to 5, which as Component (A) is a finely divided, organic or inorganic contain pigment. 7. colorant preparations according to claims 1 to 6, which as Component (B) a dispersant based on aryl sulfonic acid-formaldehyde condensation products (B1) or of contain oxalkylated phenols (B2). 8. Use of colorant preparations according to claims 1 to 7 as inks for the ink jet process. 9. Process for printing flat or three-dimensional designed substrates in the ink jet process, characterized records that colorant preparations according to claims Chen 1 to 7 printed on the substrate and the obtained If desired, the print is then fixed.