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United States Patent (19) 11 Patent Number: 5,922,118 Johnson Et Al

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United States Patent (19) 11 Patent Number: 5,922,118 Johnson Et Al USOO5922118A United States Patent (19) 11 Patent Number: 5,922,118 Johnson et al. (45) Date of Patent: *Jul. 13, 1999 54 MODIFIED COLORED PIGMENTS AND INK OTHER PUBLICATIONS JET INKS, INKS, AND COATINGS CONTAINING MODIFIED COLORED Derwent Abstract, AN No. 80-03330C, “Sulphonated Car PGMENTS bon Pigment Production by Treating Technical Grade Car bon with Hot Aqueous Acid,” SUA, 659523, Apr. 1979. 75 Inventors: Joseph E. Johnson, Nashua, N.H., Derwent Abstract, AN No. 82-28019E, “Penetrating Flexo James A. Belmont, Acton, Mass. graphic Print Ink Based Polyacrylic Resin,” Oct. 17, 1979, SU.A, 834062. 73 Assignee: Cabot Corporation, Boston, Mass. Derwent Abstract, AN No. 86-335147, “Wear Resistant Rubber Composition for Tire Tread Rubber.” Apr. 30, 1985, c: - - - JPA 61–250042, Nov. 1986. * Notice: This patent is Subject to a terminal dis Derwent Abstract, AN N. 93-261471, “Carbon Black for claimer. Coating Magnetic Recording Media-Having Silicon Diox ide Coating, Giving Good Dispersibility, Lubrication, etc.', 21 Appl. No.: 08/871,453 Japanese Patent Application No. 5178604, Jul. 20, 1993. Derwent Abstract, AN No. 95-183086, “Tire Treated Rub 22 Filed: Jun. 9, 1997 ber Composition.” Apr. 18, 1995, JPA 07102116. Derwent Abstract, AN No. 94-189154, “Ink for Writing Related U.S. Application Data Implements,” May 10, 1994, JPA 61–28517A. Derwent Abstract, AN No. 88–116672, “Surface Treat of 63 Continuation-in-part of application No. 08/663,707, Jun. 14, Carbon Black Powder Coating Disperse Water Adjust pH 1996, Pat. No. 5,707.432, and application No. 08/783,411, Add Aqueous Solution Sodium Silicate.” Mar. 22, 1988, JP Jan. 14, 1997, Pat. No. 5,803,959. 63063755 A. (51) Int. Cl. ............................................... C09D 11/02 Patent Abstracts of Japan Publication No.JP7102116, “Rub 52 U.S. Cl. .................. 106/31.6; 106/31.75; 106/31.86; ber Composition for Tire Tread.” Apr. 18, 1995. 106/476; 106/499 Moschopedis, et al., “The Reaction of Diazonium Salts with 58 Field of Search .............................. 106/31.75, 31.86, Humic Acids and Coals: Evidence for Activated Methylene 106/31.6, 476, 499 Bridges in Coals and Humic Acids.” Fuel, vol.43, No. 4, pp. 289-298, 1964, no month. Roberts et al., Basic Principles of Organic Chemistry, Sec 56) References Cited ond Edition, W.A. Benjamin, Inc., Pub., p. 1080, no date available. U.S. PATENT DOCUMENTS Zoheidi et al., “Role of Oxygen Surface Groups in Catalysis T860,001 3/1969 Gessler ................................... 260/41.5 of Hydrogasification of Carbon Black by Potassium Car 2,121,535 6/1938 Amon ........ ... 106/473 bonate,” Carbon, vol. 25, No. 6, pp. 809–819, 1987, no 2,439,442 4/1948 Amon et al. ... 23/209.1 month available. 2,793,100 5/1957 Weihe ....... ... 423/460 International Search Report for PCT/US 97/08049 mailed 2,867,540 1/1959 Harris.... ... 106/476 3,011,902 12/1961 Jordon ........... ... 106/30 R Sep. 15, 1997. 3,025,259 3/1962 Watson et al. ... 106/476 Delamar et al., J. Am. Chem. Soc. 1992, 114,5883-5884, no 3,317,458 5/1967 Clas et al. .............................. 260/41.5 month available. (List continued on next page.) Primary Examiner Helene Klemanski 57 ABSTRACT FOREIGN PATENT DOCUMENTS 0 006 190 A1 1/1980 European Pat. Off.. A modified colored pigment is described which comprises O 475 075 A1 3/1992 European Pat. Off.. colored pigment having attached at least one organic group. 0 050 354 4/1992 European Pat. Off.. The organic group comprises a) at least one aromatic group E 72775 4/1960 France. or a C-C alkyl group and b) at least one ionic group, at 1331889 5/1963 France. least one ionizable group, or a mixture of an ionic group and 1948443 4/1971 Germany. an ionizable group. The aromatic group or the C-C alkyl 2355 758 5/1975 Germany. group of the organic group is directly attached to the 56-078629 6/1981 Japan. pigment and the organic group is present at a treatment level 59/82467 5/1984 Japan. of from about 0.10 to about 4.0 micromoles/m’ of the 62/250073 10/1987 Japan. pigment used based on nitrogen Surface area of the pigment. 6067421 3/1994 Japan. Also described are aqueous and non-aqueous inkS and 862018 3/1961 United Kingdom. coatings and inkjet ink compositions containing the modi 1191872 5/1970 United Kingdom. fied colored pigment. A method to increase the flow of an ink 2 188 311 9/1987 United Kingdom. is also disclosed as well as a method to improve the WO 91/02034 2/1991 WIPO. waterfastness of a print imaged by an ink composition. Also, WO 91/15425 10/1991 WIPO. other inkjet ink compositions are described which comprise WO 92/13983 8/1992 WIPO. WO95/O1838 1/1995 WIPO. an aqueous or non-aqueous vehicle and a colored pigment WO 96/18688 6/1996 WIPO. having attached an organic group having the formula: WO 96/18694 6/1996 WIPO. Ar-R" (I) or Ar"RR (II) wherein Ar is an aromatic group WO 96/18695 6/1996 WIPO. and Ar" is an aromatic group. WO 96/18696 6/1996 WIPO. WO 96/37547 11/1996 WIPO. 77 Claims, No Drawings 5,922,118 Page 2 U.S. PATENT DOCUMENTS 5,190,582 3/1993 Shinozuka et al. ................... 106/20 D 5,281.261 1/1994 Lin ........................................ 106/20 R 3,335,020 8/1967 Aboytes et al. ........................ 106/476 5,282,887 2/1994 Gay et al. ............................... 106/261 3,423.391 1/1969 Kindler et al. ... 260/141 5,401.313 3/1995 Suppl tal 106/475 3,528,840 9/1970 Aboytes ..... ... 106/473 2 - - -a- UPPlee el al. 3,671,476 6/1972 Terai et al. - - - - - - - - - 260/23 5,554,739 9/1996 Belmont - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 534/885 3,686,111 8/1972 Makhlouf et al. ... 524/530 5,559,169 9/1996 Belmont et al. ........................ 523/215 4,006,031 2/1977 Ferch et al. ... ... 106/473 5,571,311 11/1996 Belmont et al. ...................... 106/20 R 4,014,844 3/1977 Vidal et al. ... ... 106/472 5,575,845 11/1996 Belmont et al. ........................ 106/712 4,265,768 5/1981 Beasley et al. ... 210/682 5,630,868 5/1997 Belmont et al. ..................... 106/31.75 4,320,011 3/1982 Sato et al....... ... 210/694 5,637,138 6/1997 Yamazaki ............................. 106/31.32 4,366,139 12/1982 Kühner et al ... 423/449 5,654,357 8/1997 Menashi et al. ........................ 524/495 4,452,638 6/1984 Gallus ........ ... 106/97 5,656,072 8/1997 Kato et al. .. ... 106/31.58 4,530,961 7/1985 Nguyen et al. 106/20 R 4,537,633 8/1985 Hong .............. ... 106/96 5,672,198 9/1997 Belmont ... ... 106/20 4,597.794 7/1986 Ohta et al. ..... ... 106/20 C 5,698,016 12/1997 Adams et al. 106/31.6 4,820,751 4/1989 Takeshita et al. 523/215 5,707.432 1/1998 Adams et al. - - - 106/31.6 4,831,011 5/1989 Oikawa et al. ... ... 502/406 5,713,988 2/1998 Belmont et al. ... 106/31.6 5,130,363 7/1992 Scholl et al. ... ... 524/392 5,747,562 5/1998 Mahmud et al. ....................... 106/475 5,159,009 10/1992 Wolff et al. ... 106/475 5,749,950 5/1998 Mahmud et al. ...................... 106/31.6 5,184.148 2/1993 Suga et al. ............................ 106/20 R 5,803,959 9/1998 Johnson et al. ...................... 106/31.75 5,922,118 1 2 MODIFIED COLORED PGMENTS AND INK in the Concise Encyclopedia of Polymers, Science and JET INKS, INKS, AND COATINGS Engineering, pgs. 160-171 (1990), which is incorporated CONTAINING MODIFIED COLORED herein by reference. PGMENTS Non-aqueous inks and coatings are used for many appli cations in which aqueous vehicles are not Suitable. For This application is a continuation-in-part of U.S. patent instance, inks which are to be printed on hydrophobic, application Ser. No. 08/663,707, filed Jun. 14, 1996, now non-porous Substrates Such as metal, glass, or plastics must U.S. Pat. No. 5,707.432, and Ser. No. 08/783,411, filed Jan. be fast-drying. Therefore, Solvents Such as ketones, esters, 14, 1997, now U.S. Pat. No. 5,803,959, which are incorpo alcohols, or hydrocarbons are often used instead of water. rated in their entirety by reference herein. 1O Such solvent-based inks are used widely for industrial labeling of cardboard boxes and various metal or plastic BACKGROUND OF THE INVENTION containers and components. Specific examples include news 1. Field of the Invention ink compositions and web off-set gloSS heat-Set ink compo This invention relates to modified colored pigments, Such Sitions. as modified carbon products, and inkjet inks, inks and 15 InkS and coatings are also required to be water resistant in coatings which contain modified colored pigments. The certain Situations. In Such instances, water-resistant resins present invention is further directed to ink compositions and, can be dissolved in non-aqueous Solvents of ink and coating more particularly, to acqueous ink compositions Suitable for formulations to provide the desired water resistance upon imaging applications, Such as inkjet printing processes. drying. A primary use of Such non-aqueous coatings is on 2. Discussion of the Related Art metal and plastic automotive parts. Presently, predominant black pigments are carbon blackS Inkjet printing is a non-impact process wherein droplets which can be used as colorants either in dry, powdered form, of ink are produced and deposited on a Substrate Such as a flushed paste, or a liquid dispersion form depending upon paper, transparent film, polymer sheet, or textile material in the method to apply the pigment to the Substrate and the response to an electronic Signal.
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