(12) United States Patent (10) Patent No.: US 8,232,265 B2 Rogers Et Al

(12) United States Patent (10) Patent No.: US 8,232,265 B2 Rogers Et Al

US008232265B2 (12) United States Patent (10) Patent No.: US 8,232,265 B2 Rogers et al. (45) Date of Patent: Jul. 31, 2012 (54) MULTI-FUNCTIONAL IONIC LIQUID 25. A 8. 3. MadeuZZi et al. ..... : COMPOSITIONS FOR OVERCOMING 4,491,574 A 1/1985 Seifter et al. .................... 424/10 POLYMORPHISMAND IMPARTING 4,761,164 A 8, 1988 Pez et al. .......................... 55/16 IMPROVED PROPERTIES FORACTIVE 4,973,456 A 1 1/1990 Quinn et al. 423,210.5 PHARMACEUTICAL, BIOLOGICAL, 539W - I A s 3: E.OCSC heralCal. ............. $2. NUTRITIONAL AND ENERGETIC 5,679,146 A 10/1997 Kalt et al. .......... ... 106,166.01 INGREDIENTS 5,683,832 A 1 1/1997 Bonhote et al. ............... 429,111 5,731, 101 A 3, 1998 Sherifet al. ....... ... 429,102 (75) Inventors: Robin D. Rogers, Tuscaloosa, AL (US); 5,792,399 A 8, 1998 Meister et al. ... 264/101 Daniel T. Daly, Tuscaloosa, AL (US); 5,827,602 A 10, 1998 Koch et al. ..... ... 429,194 Richard P. Swatloski, Tuscaloosa, AL 993,--- f $3. E.urgard et al......................... .. 428/402.2 556,119 (US); Whitney L. Hough, Albertville, 6,774,240 B2 8/2004 Seddon et al. ..... ... 548/347.1 AL (US); James Hilliard Davis, Jr., 6,808,557 B2 10/2004 Holbrey et al. .......... 106,163.01 Mobile, AL (US); Marcin Smiglak, 6,824,599 B2 11/2004 Swatloski et al. ....... 106,163.01 6,846,926 B1 1/2005 Koppes et al. ................ 544,198 oznanCNE (PL); Scottork K. Spear,St. EasSLOn, 6,924.3416,906,004 B2 * 8/20056/2005 MaysParrish et et al. al. ....................... 504,127526,89 AL (US) 6,939,882 B1 9/2005 Cooke et al. ... ... 514,336 6,939,974 B2 9/2005 Earle et al. .. 548/347.1 (73) Assignee: Board of Trustees of the University of 7,166,641 B2 * 1/2007 Lee et al. ... ... 514,561 Alabama, Tuscaloosa, AL (US) 2002/0010291 A1 1/2002 Murphy ............. 526,133 s s 2002/0161261 A1 10, 2002 Bahrmann et all 564,281 - 2003, OO73604 A1 4, 2003 McGolfetal. 510,441 (*) Notice: Subject to any disclaimer, the term of this 2004.0007693 A1 1/2004 Moulton ........ ... 252/.364 patent is extended or adjusted under 35 2004/0026.666 A1 2/2004 Chauvin et al. ............... 252/364 U.S.C. 154(b) by 1208 days. 2004/0146549 A1 7/2004 Ben-Sasson et al. ......... 424/449 2004/0234966 Al 11/2004 Bryning et al. ................... 435/6 (21) Appl No.: 11A545,938 2005/OO587O2 A1 3/2005 Ben-Sasson et al. ......... 424/452 y x- - - 9 2005/0136103 A1 6/2005 Ben-Sasson et al. ......... 424/449 (22) Filed: Oct. 10, 2006 (Continued) (65) Prior Publication Data FOREIGN PATENT DOCUMENTS US 2007/0093462 A1 Apr. 26, 2007 CA 2619367 A1 T 2009 (Continued) Related U.S. Application Data (60) Provisional application No. 60/764,850, filed on Feb. OTHER PUBLICATIONS 2, 2006, provisional application No. 60/724,604, filed Avent et al., “Evidence for hydrogen bonding in solutions of 1-Ethyl on Oct. 7, 2005, provisional application No. 3-imidazolium Halides, and its implications for ambient temperature 60/724,605, filed on Oct. 7, 2005. Halogenoaluminate(III) ionic liquids.” J. Chem. Soc., Dalton Trans., 3405 (1994). (51) Int. Cl. Bates et al., "CO2 capture by a task-specific ionic liquid.” J. Am. A6 IK3I/33 (2006.01) Chem. Soc. 124(6): 926-927 (2002). A6 IK3I/445 (2006.01) Bernstein, “Polymorphism of high energy materials.” Polymorphism A6 IK3I/21 (2006.01) in Molecular Crystals, 275-296 (2002). A6 IK3I/24 (2006.01) Bernstein, “Introduction and historical background.” Polymorphism A6 IK3I/6 (2006.01) in Molecular Crystals, 1-28 (2002). AOIN 43/90 (2006.01) Bernstein, “Crystal structure prediction and polymorphism.” ACA AOIN 37/30 (2006.01) Transactions, 39:14-23 (2004). AOIN37/18 (2006.01) (52) U.S. Cl. ........ 514/183; 514/306; 514/330; 514/513; (Continued) 514/535; 514/555 Primary Examiner — Alton Pryor (58) Fieldee application t state file for completeSeash - -search - - - - - - - -hhi history. - - - - - - - - None &(74) Curfman, Attorney, LLC Agent, or Firm — McKeon, Meunier, Carlin (56) References Cited (57) ABSTRACT U.S. PATENT DOCUMENTS Disclosed are ionic liquids and methods of preparing ionic 1943,176 A 1/1934 Graenacher ................... 260/100 liquid compositions of active pharmaceutical, biological, 2,004,891 A * 6/1935 Goldberg ...................... 514,533 nutritional, and energetic ingredients. Also disclosed are 3,223,704 A 12, 1965 Shibe ... ... 260,247.1 methods of using the compositions described herein to over 3. As A 3. E. St. .364;2. come polymorphism, overcome solubility and delivery prob 3.47 1423 A 10, 1969 Elmer ....... ... 260/22 lems, to control release rates, add functionality, enhance effi 4,104,368 A 8, 1978 Lala et al. 424,60 cacy (synergy), and improve ease of use and manufacture. 4,171,352 A * 10/1979 Wolgemuth et al. ... 436/86 4,188,263. A 2, 1980 Hulsmann et al. ............ 439/179 9 Claims, 6 Drawing Sheets US 8,232,265 B2 Page 2 U.S. PATENT DOCUMENTS Cuppen et al., “Crystal structure and growth behavior of aspartame 2005, 0194561 A1 9/2005 Davis .............................. 252/67 form I-A.” Crystal Growth & Design, 5(3) 917-923 (2005). 2005/0232981 A1 10, 2005 Ben-Sasson .................. 424/448 Davis et al., “Thiazolium-ion based organic ionic liquids (OILS). 2006, O159632 A1 7/2006 Ishibashi et al. Novel OILs which promote the benzoin condensation.” Tetrahedron 2007/0053939 A1 3/2007 Yokoyama et al. Lett. 40: 1621-1622 (1999). 2007/0054952 A1 3/2007 Hamamoto et al. 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