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(12) United States Patent (10) Patent No.: US 8,409,343 B2 Niewold Et Al

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(12) United States Patent (10) Patent No.: US 8,409,343 B2 Niewold Et Al USOO8409343B2 (12) United States Patent (10) Patent No.: US 8,409,343 B2 Niewold et al. (45) Date of Patent: *Apr. 2, 2013 (54) ORGANIC-INORGANIC HYBRD PGMENT (56) References Cited COMPOSITIONS U.S. PATENT DOCUMENTS (75) Inventors: Lori A. Niewold, Anthony, NM (US); 4,381,948 A 5/1983 McConnell et al. Robyn Torres, El Paso, TX (US); Gary 4,842,903. A 6/1989 Hayner 5,759,256 A 6/1998 Stramel E. Williams, El Paso, TX (US) 6,495,250 B1 12/2002 Schacht et al. 6,503,970 B1 1, 2003 Valin (73) Assignee: Mayan Pigments, Inc., El Paso, TX 7,052,541 B2 5, 2006 Chianelli et al. 7.425,235 B2 * 9/2008 Chianelli et al. .............. 106,487 (US) 7,429,294 B2 * 9/2008 Chianelli et al. ... ... 106,401 8,123,850 B2 * 2/2012 Niewold ....................... 106,487 (*) Notice: Subject to any disclaimer, the term of this 2005/OOOT680 A1 1/2005 Naganuma et al. patent is extended or adjusted under 35 2005/0207002 A1 9, 2005 Liu et al. U.S.C. 154(b) by 142 days. 2007/0012349 A1 1/2007 Gaudiana et al. 2007/02777O2 A1 12/2007 Chianelli et al. This patent is Subject to a terminal dis 2008.0031508 A1 2/2008 Baloukas et al. claimer. 2008/0216711 A2 9, 2008 Heubach 2010/0298482 A1 11/2010 Niewold et al. (21) Appl. No.: 12/863,558 2011/0113986 A1 5, 2011 Niewold et al. FOREIGN PATENT DOCUMENTS (22) PCT Fled: Jan. 21, 2009 JP 49-005433 A * 1, 1974 JP 3-216306 A * 9, 1991 (86) PCT NO.: PCT/US2009/031570 OTHER PUBLICATIONS S371 (c)(1), English translation of International Preliminary Report on Patent (2), (4) Date: Jul.19, 2010 ability and Written Opinion issued in International Application No. PCT Pub. No.: WO2O09/O92103 PCT/US2009/031570 dated Jul. 29, 2010. (87) United States Office Action issued in U.S. Appl. No. 12/921,998 PCT Pub. Date: Jul. 23, 2009 dated Jul. 15, 2011. United States Office Action issued in U.S. Appl. No. 12/922,013 (65) Prior Publication Data dated Jul. 15, 2011. US 2010/O298482 A1 Nov. 25, 2010 * cited by examiner Primary Examiner — Anthony J Green Related U.S. Application Data (74) Attorney, Agent, or Firm — McDermott Will & Emery LLP (60) Provisional application No. 61/021,787, filed on Jan. 17, 2008, provisional application No. 61/044,608, (57) ABSTRACT filed on Apr. 14, 2008. An organic-inorganic hybrid pigment composition is pro Vided comprising an organic pigment, an inorganic pigment, (51) Int. C. and a fibrous clay. The fibrous clay can be selected from C09B 67/22 (2006.01) palygorskite, Sepiolite, or a combination thereof. The inor C04B I4/10 (2006.01) ganic pigment is selected from rutile pigments, spinel pig C04B I4/38 (2006.01) ments, bismuth Vanadate pigments, cerium sulfide pigments, C09B 67/00 (2006.01) and combinations thereof. The organic pigment is selected C09B 67/02 (2006.01) from anthraquinone pigments, anthrathrone pigments, (52) U.S. C. ........ 106/487: 106/410; 106/412: 106/413; anthrapyrimidine pigments, azo pigments, azomethine pig 106/440; 106/441; 106/447: 106/453; 106/479; ments, quinacridone pigments, quinophthalone pigments, 106/486; 106/493: 106/494; 106/495; 106/496; diketopyrrolopyrrol pigments, inanthrone pigments, isoindo 106/497: 106/498; 106/811; 524/445 line pigments, metal complex pigments, perinone pigments, (58) Field of Classification Search .................. 106/486, perylene pigments, phthalocyanine pigments, pyranthrone 106/487, 81,811, 410, 412, 413, 440, 441, pigments, pyrazolo-quinaZolone pigments, thioindigo pig 106/447, 453,479, 493, 494, 495, 496, 497, ments, and combinations thereof. 106/498: 524/445 See application file for complete search history. 17 Claims, 7 Drawing Sheets U.S. Patent Apr. 2, 2013 Sheet 1 of 7 US 8,409,343 B2 FIG. 1 30% TR643PS2O WITH 70% MA50 BEFORE HEATING W.S. 30% TR643PS2O WITH 70%. MASO s al t "O s o e O 200 14. SOO 300, 2000,0 Wavelength (cm-1} U.S. Patent Apr. 2, 2013 Sheet 2 of 7 US 8,409,343 B2 FIG 2 30%TG504K witH 70% MA5o BEFORE HEATING WS. 30% TGSO4K WITH 70% MASO AFTER HEANG 30% GC4KWTO%. MASOBEFOR. -EANG Kwan' wisra was 30% SS 4KWTH FO% MASOAFTER-EANG yeva.........................w...iii... 800. OOOO 2O.O. 4OOO 1600 8:00) Wavelength cm-li) U.S. Patent Apr. 2, 2013 Sheet 3 of 7 US 8,409,343 B2 FIG. 3 8.000 6.00 4.OOO 2. 0000 2000 -4000 6,000 -8,000 500 100, 1500 20. 2500 3000 3S.O. 4000 4500 TempCel - 30% Tico" Green 504K with 70% Milled Attagel 50 before heated - 30% Tico" Green 504K with 70% Milled Attagel 50 after heated U.S. Patent Apr. 2, 2013 Sheet 4 of 7 US 8,409,343 B2 FIG. 4 20 11. OOO 3.OO 8.0 70 a. 5.00 N 4.0 3.0 200 1CO SCO 1000 150 2000 2500 3000 3500 400 450 TempCel - 30% Tico "Red 643 PS20 with 70% Milled Attagel 50 before heated - 30% Tico "Red 643 PS20 with 70%. Milled Attagel 50 after heated U.S. Patent Apr. 2, 2013 Sheet 5 Of 7 US 8,409,343 B2 FIG. 5 N B P C 1 B 40 5 8 20 400 1s 1800 2600 28 O 3 OOO 3200 34 360 c 38) 4 000 W a we unber U.S. Patent Apr. 2, 2013 Sheet 6 of 7 US 8,409,343 B2 FIG 6 NB PC 1 1 C 400 600 800 1000 2 1400 solo 800 3000 3200 3400 3600 38 4000 Wave number U.S. Patent Apr. 2, 2013 Sheet 7 Of 7 US 8,409,343 B2 FIG. T. N B P C 1 1 C 1 4 0 1 s 00 800 W a we number US 8,409,343 B2 1. 2 ORGANIC-INORGANIC HYBRD PGMENT duced the color of Maya blue but the mixture did not possess COMPOSITIONS the same chemical properties as the original organic/inor ganic complex Samples. RELATED APPLICATIONS Previous literature discussions of pH pertain to the alkaline pH required to reduce the indigo prior to contacting it with the This application is the U.S. National Phase under 35 U.S.C. clay (Littman, Amer: Antiquity, 45:87-101, 1980; Littman, S 371 of International Application No. PCT/U.S.2009/ Amer: Antiquity, 47:404–408, 1982). Moreover, there was a 031570, filed on Jan. 21, 2009, which in turn claims the lack of understanding regarding the chemistry for producing benefit of U.S. Provisional Application Ser. No. 61/021,787, stable and nontoxic paint systems by combining dyes and filed Jan. 17, 2008 and U.S. Provisional Application Ser. No. 10 pigments with fibrous clays. U.S. Pat. No. 3,950,180 61/044,608, filed Apr. 14, 2008. This application discloses describes color compositions that involve cationic organic subject matter similar to that disclosed in U.S. Pat. Nos. basic colored compounds complexed to alkali-treated inor 7,052,541; 7,425,235; and 7,429.294; and U.S. application ganic Substances. Ser. No. 1 1/424,758, filed Jun. 16, 2006, now abandoned; and 15 More recently, several patents and patent applications dis U.S. application Ser. No. 12/068,115 filed Feb. 1, 2008, now cussed indigo and related organic dyes complexed in an ionic abandoned. The contents of each herein incorporated by ref interaction withinorganic supports. PCT Publication No. WO erence in their entirety. 01/04216 also describes ionic interactions in color composi tions, wherein organic dyes undergo ion exchange with FIELD OF THE INVENTION charged inorganic clays. U.S. Pat. No. 3.950,180 covers a method of manufacturing This invention relates to hybrid pigment compositions color compositions that include Zeolite and montmorillonite. comprising organic colorants and an inorganic fibrous clay U.S. Pat. No. 5,061,290 covers a method of using indigo and methods of preparing Such compositions. derivatives as a dyeing agent. U.S. Pat. No. 4,246,036 covers 25 the method of manufacturing color compositions that are BACKGROUND comprised of asbestos-cement. U.S. Pat. No. 4,640,862 cov ers color compositions that are used for coating an expanded In the scientific literature, the term Maya blue refers to a polystyrene “drop-out' ceiling tile. U.S. Pat. No. 4,868,018 “turquoise' brilliant shade of blue that is found on murals and covers color compositions that are used with a mixture of archaeological artifacts, for example, throughout 30 epoxy resin, epoxy resin hardener, and portland cement to Mesoamerica. It is described in the literature as being com form a coating which can be applied to a Surface to form posed of palygorskite clay and indigo, that when mixed and simulated marble products. U.S. Pat. No. 4,874,433 covers a heated, produce the stable brilliant blue color similar to that method for encapsulating color compositions in and/or to a found in Mesoamerica. Proposed methods of preparation Zeolite. U.S. Pat. No. 5,574,081 covers a method of manufac were performed with the intent of trying to replicate the blue 35 turing waterborne clay-containing emulsion paints with color found at the historical sites and to reproduce the tech improved application performance using color compositions. niques employed by the original Maya. U.S. Pat. No. 5,972,049 covers the method of manufacturing H. Van Olphen, Rutherford Gettens, Edwin Littman, Anna and using color compositions to form dye carriers used in the Shepard, and Luis Torres were involved in the examination of dyeing process for hydrophobic textiles.
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