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(19) United States (12) Patent Application Publication (10) Pub US 20060119679Al (19) United States (12) Patent Application Publication (10) Pub. No.: US 2006/0119679 A1 Kruger et a]. (43) Pub. Date: Jun. 8, 2006 (54) DRAWING LIQUIDS (22) PCT Filed: Sep. 25, 2003 (75) Inventors: Christian Kruger, Saulheim (DE); (86) PCT No.: PCT/EP03/10656 Ulrike Hees, Mannheim (DE); Richard Van Gelder, Speyer (DE); Peter (30) Foreign Application Priority Data Fuber, Habloch (DE); Lothar Schulz, Nubloch (DE); Hans-Gumer Sep. 27, 2002 (DE) ................................... .. 102 45 209.1 Bohrmann, LudWigshafen (DE); Dieter Puttner, Sandhausen (DE); Sophia Publication Classi?cation Ebert, Mannheim (DE) (51) Int. Cl. Correspondence Address: G01D 11/00 (200601) OBLON, SPIVAK, MCCLELLAND, MAIER & (52) US. Cl. ............................................................ .. 347/100 NEUSTADT, RC. 1940 DUKE STREET ALEXANDRIA, VA 22314 (US) (57) ABSTRACT (73) Assignee: BASFAktiengesellschaft,LudWigshafen (DE) Disclosed are recording ?uids, preferably inks for the ink jet process, containing random polyurethane copolymers and (21) Appl. No.: 10/529,210 one or more melamine derivatives as crosslinkers. US 2006/0119679 A1 Jun. 8, 2006 DRAWING LIQUIDS [0009] WO 00/03081 describes a process for printing textile substrates using the ink jet printing process by [0001] The present invention relates to recording ?uids, pretreatment of the substrate With a binder. This process especially inks for ink jet printing. requires an additional operation. It is economically sensible [0002] Inks for use in the ink jet process (such as PieZo Ink to develop an ink Which renders this additional operation Jet, continuous Ink Jet, Valve Jet) have to meet a Whole unnecessary. HoWever, prior art dispersants are not useful as series of requirements. They have to have a viscosity and an ingredient of these inks. surface tension suitable for printing, they have to be stable [0010] It is an object of the present invention to remedy in storage, i.e., they should not coagulate or ?occulate, and the disadvantages of the prior art and provide novel record they must not lead to cloggage of the printer noZZle, Which ing ?uids Which in particular have a loW viscosity and can be problematical especially in the case of pigmented produce prints having good ?xation, color strength and inks, i.e., containing colorant particles Which are insoluble in brilliance and good in-service fastnesses (Washfastness and the medium. Stability in storage further in storage further Wet and dry rubfastness). requires of these inks that the dispersed colorant particles do not sediment. Furthermore, in the case of Continuous Ink Jet [0011] We have found that this object is achieved by the inks shall be stable to the addition of conducting salts recording ?uids containing random polyurethane copoly and be free from any tendency to ?ock out With an increase mers and melamine derivatives as crosslinkers. in the ion content. In addition, the prints obtained have to [0012] The recording ?uids additionally containing meet colorists’ requirements, i.e., shoW brilliance and depth organic or inorganic colorants, optionally further dispers of shade, and have good fastness properties, for example, ants, solvents and also customary additives. lightfastness, and good drying characteristics. [0013] Random polyurethane copolymers [0003] These requirements can be met by means of suit able dispersing additives. The literature discloses various [0014] Random polyurethane copolymers are obtained dispersing additives Whose properties have to be further from one or more different di- or polyisocyanates and one or optimiZed, hoWever. more different further compounds Which have at least tWo isocyanate-reactive groups. The units derived from the [0004] After a substrate, for example a textile substrate, diisocyanates on the one hand and the further compounds on has been printed, the inks should remain on the substrate and the other alternate, and When tWo or more different isocy should certainly not be redispersed in a Wash liquor used for anates and tWo or more different further compounds are used Washing the textile for example. This requires the addition of these units Will each be present in a random distribution in a binder to the ink or a corresponding treatment of the textile the polymer formed. Random polyurethane copolymers, shortly before or after printing, and this requires an addi accordingly, do not have a block structure. tional operation. [0015] Polyurethanes for the purposes of the present [0005] WO 00/17250 describes the use of dispersants invention are not only polymers Which are exclusively having a block copolymer structure consisting of a di- or linked by urethane groups but in a more general sense polyfunctional isocyanate and a block Which is terminated polymers Which are obtainable by reaction of di- or poly With a polar group, for example COOH, and Whose end isocyanates With compounds containing active hydrogen group has been reacted With for example polyamides or atoms. Polyurethanes for the purposes of the present inven vinyl-bearing N-containing heterocycles. Inks produced tion, as Well as urethane groups, can also contain urea, using such dispersants have very good properties With allophanate, biuret, carbodiimide, amide, ester, ether, ure regard to rubfastness and Waterfastness, but in the case of tonimine, uretidione, isocyanurate or oxaZolidine groups. An prints on textile the level of ?xation reveals a need for example of a survey is Kunststo?handbuch/Saechtling, 26th optimiZation after several Washes. Similarly, ?xation edition, Carl-Hanser-Verlag, Munich 1995, page 491 if. decreases substantially in the case of substrates Which are More particularly, polyurethanes for the purposes of the bent, folded or creased. present invention can contain urea groups. [0006] WO 99/41320 describes ink jet printing inks dis [0016] To prepare random polyurethane copolymers, one persed using polyurethanes having for example dimethylol or more diisocyanates are reacted by knoWn methods With propionic acid or polyethylene monomethyl ether as dis one or more compounds bearing tWo isocyanate-reactive persing groups, randomly distributed across the molecule. groups. In addition, the reaction mixture may also contain a The inks produced using the polyurethanes described are certain amount of compounds having just one isocyanate notable for good storage stability and good to moderate reactive group. The NCO groups of the diisocyanate or printing properties, especially With regard to noZZle failure, diisocyanates can have the same or a different reactivity. but the ?xation of the prints is too loW for commercial Diisocyanates having NCO groups of the same reactivity applications. may be aromatic or aliphatic diisocyanates, preference being [0007] WO 99/50364 describes the use of polyurethanes given to aliphatic diisocyanates such as tetramethylene as dispersants in ink jet inks comprising a Water-soluble diisocyanate, hexamethylene diisocyanate, octamethylene solvent, a Water-insoluble solvent and Water. The polyure diisocyanate, decamethylene diisocyanate, dodecamethyl thanes contain dispersing, i.e., Water-solubiliZing, groups ene diisocyanate, tetradecamethylene diisocyanate, trimeth randomly distributed across the molecule. HoWever, the ylhexane diisocyanate, tetramethylhexane diisocyanate, 1,4-, 1,3- or 1,2-diisocyanatocyclohexane, 4,4'-di(isocyana ?xation of the ink is still capable of improvement. tocyclohexyl)methane, 1-isocyanato-3,3,5-trimethyl-5-(iso [0008] EP-A 0 739 959 describes random polyurethane cyanatomethyl)cyclohexane (isophorone diisocyanate) and copolymers and their use as dispersants. 2,4- and 2,6-diisocyanato-1-methylcyclohexane, of Which US 2006/0119679 A1 Jun. 8, 2006 hexamethylene diisocyanate (HDI) and isophorone diisocy dilaurate or the dialkyl derivatives of tin dialkyl salts of anate are particularly preferred. Further particularly pre aliphatic carboxylic acids such as dibutyltin diacetate, dibu ferred diisocyanates are m-tetramethylxylene diisocyanate tyltin dilaurate or the like. The catalysts are customarily used (TMXDI) and 4,4'-diphenylmethane diisocyanate. in amounts of from 0.0001 to 0.1 part by Weight per 100 parts by Weight of diol or diamine. [0017] Preferred diisocyanates having NCO groups of differing reactivity are the readily and inexpensively avail [0025] The synthesis of the random polyurethane copoly able isocyanates such as for example 2,4-tolylene diisocy mers is generally carried out Without a solvent or in an anate (2,4-TDI), 2,4'-diphenylmethane diisocyanate (2,4' aprotic solvent, for example in tetrahydrofuran, diethyl MDI), triisocyanatotoluene as representatives of aromatic ether, diisopropyl ether, chloroform, dichloromethane, di-n diisocyanates or aliphatic diisocyanates, such as 2-butyl-2 butyl ether, acetone, N-methylpyrrolidone (NMP), xylene, ethylpentamethylene diisocyanate, 2-isocyanatopropylcy toluene, methyl ethyl ketone (MEK), methyl isobutyl ketone clohexyl isocyanate, 2,4,4- or 2,2,4-trimethylhexamethylene (MIBK) or 1,4-dioxane. Preferred reaction temperatures are diisocyanate, 2,4'-methylenebis(cyclohexyl)diisocyanate in the range from 100 C. to the boiling point of the solvent and 4-methylcyclohexane-1,3-iisocyanate (H-TDI). used. The reaction is generally carried out under atmo [0018] Further examples of isocyanates having groups spheric pressure, but it may also be carried out in autoclaves differing in reactivity are 1,3-phenylene diisocyanate, 1,4 at up to 20 bar. phenylene diisocyanate, 1,5-naphthylene
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