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(12) United States Patent (10) Patent No.: US 8,507,585 B2 Hosoya Et Al

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(12) United States Patent (10) Patent No.: US 8,507,585 B2 Hosoya Et Al US008507585B2 (12) United States Patent (10) Patent No.: US 8,507,585 B2 Hosoya et al. (45) Date of Patent: *Aug. 13, 2013 2010/0136236 A1* 6/2010 Hosoya et al. ................ 427,261 (54) NON-AQUEOUS PIGMENT INK 2012/0083567 A1* 4/2012 Hosoya et al. ... ... 524,516 (75) Inventors: Tetsuo Hosoya, Ibaraki-ken (JP); 2012/0220702 A1* 8/2012 Hosoya et al. .................. 524.88 Hiroshi Hayashi, Ibaraki-ken (JP); FOREIGN PATENT DOCUMENTS Yoshifumi Watanabe, Ibaraki-ken (JP); CN 101001905. A 7/2007 Kazuyuki Ando, Ibaraki-ken (JP); CN 101OO7917 A 8, 2007 Marie Morinaga, Ibaraki-ken (JP) CN 101.154038 A 4/2008 EP 1205815 A1 5, 2002 Assignee: Riso Kagaku Corporation, Tokyo (JP) EP 15O2935 A1 2, 2005 (73) JP 10-060353 A 3, 1998 JP 2000-1193.61 A 4/2000 (*) Notice: Subject to any disclaimer, the term of this JP 2004-231870 A 8, 2004 patent is extended or adjusted under 35 JP 2005-239.947 A 9, 2005 U.S.C. 154(b) by 293 days. JP 2007-131753. A 5/2007 JP 2007-197500 A 8, 2007 This patent is Subject to a terminal dis JP 2007-277397 A 10/2007 claimer. JP 2008-019333 A 1, 2008 TW 200808918 A 2, 2008 (21) Appl. No.: 12/990,379 OTHER PUBLICATIONS PCT Fled: Apr. 8, 2009 (22) Form PCT/IB1338 (Notification of Transmittal of Translation of the PCT/UP2009/057.192 International Preliminary Reporton Patentability (Chapter I or Chap (86). PCT No.: ter II of the Patent Cooperation Treaty)) for International Application S371 (c)(1), No. PCT/JP2009/057192, with a mailing date of Jan. 20, 2011, one (2), (4) Date: Oct. 29, 2010 (1) page. English translation of the International Preliminary Report on Pat (87) PCT Pub. No.: WO2009/142075 entability (Chapter I of the Patent Cooperation Treaty), issued Jan. 11, 2011, for International Application No. PCT/JP2009/057192, PCT Pub. Date: Nov. 26, 2009 eight (8) pages. Search Report, issued on Sep. 4, 2012, in the counterpart European (65) Prior Publication Data Application, Application No. EP 0975 0437, four (4) pages. US 2011 FOO46298 A1 Feb. 24, 2011 Official Action, issued on Jan. 10, 2013, in the counterpart Chinese application, in Chinese, eight (8) pages. (30) Foreign Application Priority Data * cited by examiner May 23, 2008 (JP) ................................. 2008-135274 Nov. 18, 2008 (JP) ................................. 2008-294.829 Primary Examiner — Patrick Niland (51) Int. Cl. (74) Attorney, Agent, or Firm — Nath, Goldberg & Meyer; CSF 8/30 (2006.01) Jerald L. Meyer, Sanjana Mangalagiri CSF28.3/04 (2006.01) C08G 18/08 (2006.01) (57) ABSTRACT C08G 18/10 (2006.01) C08G 18/28 (2006.01) A non-aqueous pigment ink comprising a pigment, a non C83/00 (2006.01) aqueous solvent, and non-aqueous resin dispersion micropar CSK 3/20 (2006.01) ticles having a pigment dispersion capability, wherein the COSL 39/00 (2006.01) non-aqueous resin dispersion microparticles are an acrylic COSL 73/00 (2006.01) polymer comprising an alkyl (meth)acrylate unit having an (52) U.S. C. alkyl group of 12 or more carbon atoms and a (meth)acrylate USPC ........... 523/160; 523/161:524/555; 524/589; unit having aurethane group. The acrylic polymer is a copoly 524/590; 524/591; 524/839; 524/840; 525/123; mer of a monomer mixture comprising an alkyl (meth)acry 525/455; 525/920 late (A) having an alkyl group of 12 or more carbonatoms and (58) Field of Classification Search a reactive (meth)acrylate (B) having a functional group USPC ................. 523/160, 161; 524/589, 590,591, capable of reacting with an amino group, wherein the ure 524/839, 840, 555; 525/123,455, 920 thane group is introduced by a reaction between the func See application file for complete search history. tional group capable of reacting with an amino group, an amino alcohol and a polyvalent isocyanate compound, and (56) References Cited the mass ratio within the acrylic polymer between the copoly mer portion and the introduced urethane group portions is U.S. PATENT DOCUMENTS within a range from 60:40 to 99:1. 7,214,725 B2 5/2007 Narayan-Sarathy et al. 2007/0173560 A1* 7, 2007 UoZumi ........................ 523,160 2009/00928O1 A1 4/2009 Sato et al. 8 Claims, No Drawings US 8,507,585 B2 1. 2 NON-AQUEOUS PIGMENT INK Solvent, and non-aqueous resin dispersion microparticles having a pigment dispersion capability, wherein This is a National Phase Application filed under 35 U.S.C. the non-aqueous resin dispersion microparticles are an S371 as a national stage of PCT/JP2009/057192, filed on Apr. acrylic polymer comprising an alkyl (meth)acrylate unit hav 8, 2009, claiming the benefit of Japanese Patent Application 5 ing an alkyl group of 12 or more carbon atoms and a (meth) 2008-135274, filedon May 23, 2008, and claiming the benefit acrylate unit having a urethane group, of Japanese Patent Application 2008-294829, filed on Nov. the acrylic polymer is a copolymer of a monomer mixture 18, 2008, the content of each of which is hereby incorporated comprising an alkyl (meth)acrylate (A) having an alkyl group by reference in its entirety. of 12 or more carbon atoms and a reactive (meth)acrylate (B) 10 having a functional group capable of reacting with an amino TECHNICAL FIELD group, wherein the urethane group is introduced by a reaction between the functional group capable of reacting with an The present invention relates to a non-aqueous pigment amino group, an amino alcohol and a polyvalent isocyanate ink, and relates particularly to a non-aqueous pigment ink that compound, and is suitable for use in an inkjet recording system. 15 the mass ratio within the acrylic polymer between the copolymer portion and the introduced urethane group por BACKGROUND ART tions is within a range from 60:40 to 99:1. Another aspect of the present invention provides a pigment The coloring materials for inks used in inkjet recording dispersant for a non-aqueous pigment ink, wherein systems can be broadly classified into materials that use pig the pigment dispersant is composed of an acrylic polymer ments and materials that use dyes, and there is a growing comprising an alkyl (meth)acrylate unit having an alkyl group tendency for the use of inks that use pigments as the coloring of 12 or more carbon atoms and a (meth)acrylate unit having materials, as such inks exhibit the excellent levels of light a urethane group, and is insoluble in solvents having a 50% resistance, weather resistance and water resistance that are distillation point of 150° C. or higher, required for high image quality printing. 25 the acrylic polymer is a copolymer of a monomer mixture In terms of the solvent, inks can be broadly classified into comprising an alkyl (meth)acrylate (A) having an alkyl group aqueous inks and non-aqueous inks. Non-aqueous inks that of 12 or more carbon atoms and a reactive (meth)acrylate (B) do not use water as the ink solvent, including solvent-based having a functional group capable of reacting with an amino inks that use a volatile solvent as the main constituent and group, wherein the urethane group is introduced by a reaction oil-based inks that use a non-volatile solvent as the main 30 between the functional group capable of reacting with an constituent, exhibit good drying properties to aqueous inks, amino group, an amino alcohol and a polyvalent isocyanate and also display excellent printability. compound, and In non-aqueous inks, a pigment dispersant that dissolves in the mass ratio within the acrylic polymer between the the solvent is generally used, but because this pigment dis copolymer portion and the introduced urethane group por persant improves the affinity between the solvent and the 35 tions is within a range from 60:40 to 99:1. pigment, when the solvent penetrates into the recording paper, the pigment tends to be also drawn into the interior of Effects of Invention the recording paper. As a result, the print density tends to fall, and show-through becomes more prevalent. The non-aqueous ink according to the present invention Accordingly, a non-aqueous pigment ink has been pro 40 (hereafter also referred to as simply “the ink”) uses, as a posed that uses as a dispersant non-aqueous resin dispersion pigment dispersant, non-aqueous resin dispersion micropar microparticles (NAD=Non Aqua Dispersion) having a pig ticles composed of an acrylic polymer comprising an alkyl ment dispersion capability. (meth)acrylate unit having an alkyl group of 12 or more Prior Art Documents carbon atoms and a (meth)acrylate unit having a urethane Patent Documents 45 group. These non-aqueous resin dispersion microparticles Patent Document 1: Japanese Patent Laid-OpenNo. 2007 undergo a powerful interaction (adsorption) with the pig 197500 ment, and therefore image show-through on the printed item can be reduced, and the storage stability of the ink can be DISCLOSURE OF INVENTION improved. Moreover, because even a small amount of the 50 non-aqueous resin dispersion microparticles is capable of Problems Invention Aims to Solve generating a satisfactory pigment dispersion effect, the vis cosity of the ink can be suppressed to a low level, thereby By using a pigment dispersant that does not dissolve in the enabling the discharge stability to be improved when the ink Solvent, the above non-aqueous ink is able to provide is used as an inkjet ink. improved print density for printed items on plain paper. How 55 ever, according to investigations conducted by the inventors BEST MODE FOR CARRYING OUT THE of the present invention, further improvements are still INVENTION required in terms of the pigment dispersion stability.
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