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(12) United States Patent (10) Patent No.: US 8,197,692 B2 Mallet Et Al

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(12) United States Patent (10) Patent No.: US 8,197,692 B2 Mallet Et Al US008197692B2 (12) United States Patent (10) Patent No.: US 8,197,692 B2 Mallet et al. (45) Date of Patent: Jun. 12, 2012 (54) POROUS MATERIALS FOR SOLID PHASE (56) References Cited EXTRACTION AND CHROMATOGRAPHY AND PROCESSES FOR PREPARATION AND U.S. PATENT DOCUMENTS USE THEREOF 2,540,985 A 2f1951 Jackson 2,788,331 A 4, 1957 Greer et al. (75) Inventors: Claude R. Mallet, Attleboro, MA (US); 2,801.224 A 7, 1957 Greer John E. O'Gara, Ashland, MA (US); 2,824,844 A 2f1958 Gilwood Darryl W. Brousmiche, Grafton, MA 3,499,960 A 3, 1970 Stauffer et al. 3,816,355 A 6, 1974 Clemens (US) 3,946,749 A 3/1976 Papantoniou 3,954,682 A 5, 1976 Fein et al. (73) Assignee: Waters Technologies Corporation, 3,985,540 A 10, 1976 Fein et al. Milford, MA (US) 3,991,018 A 1 1/1976 Strop et al. 4,000,098 A 12/1976 Hofstee (*) Notice: Subject to any disclaimer, the term of this 4,101.461 A 7/1978 Strop et al. patent is extended or adjusted under 35 U.S.C. 154(b) by 54 days. (Continued) FOREIGN PATENT DOCUMENTS (21) Appl. No.: 12/790.795 EP O852334 7, 1998 (22) Filed: May 28, 2010 (Continued) (65) Prior Publication Data OTHER PUBLICATIONS US 2010/O3OO972A1 Dec. 2, 2010 Lieto, J. et al. “Polymer supports for catalysts.” Chemtech. 46-53 Related U.S. Application Data (1983). (63) Continuation of application No. 10/782.397, filed on (Continued) Feb. 18, 2004, now Pat. No. 7,731,844, which is a continuation-in-part of application No. 10/169,546, Primary Examiner — Ernest G. Therkorn filed as application No. PCT/US99/13241 on Jun. 10, (74) Attorney, Agent, or Firm – Edwards Wildman Palmer 1999, now Pat. No. 7,232,520. LLP, Peter C. Lauro, Esq.; Mark D. Russett (60) Provisional application No. 60/089,153, filed on Jun. 12, 1998. (57) ABSTRACT (51) Int. Cl. Embodiments of the present invention are directed to porous BOLD I5/08 (2006.01) materials for use in Solid phase extractions and chromatogra (52) U.S. Cl. ..................... 210/635: 210/656; 210/198.2: phy. The materials feature at least one hydrophobic compo 21 O/5O2.1 nent, at least one hydrophilic component and at least one (58) Field of Classification Search .................. 210/634, ion-exchange functional group. The materials exhibit Supe 210/635,656,659, 1982; 96/101: 502/.402; rior wetting and ion-exchange performance. 521/32, 33: 525/326.9, 330.3, 330.4, 330.5 See application file for complete search history. 2 Claims, 2 Drawing Sheets dY. Woxo OO 4.38 0.50 OO SO 2.OO 250 3.00 350 400 450 500 time US 8,197.692 B2 Page 2 U.S. PATENT DOCUMENTS 6,362,245 B1 3, 2002 Takahashi et al. 6,686,035 B2 2, 2004 Jiang et al. 4,192,921 3, 1980 Dales 6,946,070 B2 9, 2005 Hammen et al. 4,297.220 10, 1981 Meitzner et al. 7,232,520 B1 6, 2007 Lee et al. 4,303,531 12, 1981 Kawabata et al. 7,442,299 B2 10/2008 Lee et al. 4,468,330 8, 1984 Kamiyama et al. 7,731,844 B2* 6/2010 Mallet et al. ............... 210, 1982 4,523,959 6, 1985 Exertier 8,048,305 B2 * 1 1/2011 Lu et al. ........................ 210/635 4,622.288 11, 1986 Yokoyama et al. 2002, 0004561 A1 1, 2002 Takahashi et al. 4,711,863 12, 1987 Streat et al. 2002.0043499 A1 4, 2002 Hammen et al. 4,758.413 T. 1988 Harris et al. 2007/020515.6 A1 9, 2007 Lee et al. 4,789.479 12, 1988 Onitsuka et al. 2009,0139323 A1 6, 2009 Lee et al. 4,828,710 5, 1989 Itoh et al. 4,889,632 12, 1989 Svec et al. FOREIGN PATENT DOCUMENTS 4,923,610 5, 1990 Svec et al. 4,933,372 6, 1990 Feilbush et al. EP O982326 3, 2000 4,952,349 8, 1990 Svec et al. EP 1159.995 A2 12/2001 4.954,262 9, 1990 Aoki et al. JP 2002-187904. A T 2002 5,030,352 7, 1991 Varady et al. WO WO95/30467 11, 1995 5,230,806 7, 1993 Fritz et al. WO WO99,6448O 12/1999 5,238,992 8, 1993 Outubuddin WO WOOOf73782 12/2000 5,278.339 1, 1994 Cook 5,292.818 3, 1994 Oishi et al. OTHER PUBLICATIONS 5,292,828 3, 1994 Jenkins et al. 5.431,807 7, 1995 Frechet et al. Mitchell, A. R. et al. "Preparation of aminomethyl-polystyrene resin 5.453,185 9, 1995 Frechet et al. by direct amidomethylation, Tetrahedron Letters. 42: 3795-8 5,587,323 12, 1996 Lewis et al. (1976). 5,618,438 4, 1997 Fritz et al. Unger, K. “Packings and stationary phases in chromatographic tech 5,728.457 3, 1998 Frechet et al. niques.” Chromatographic Science Series. 47: 585-720 (1990). 5,840,911 11, 1998 Frei et al. 5,882,521 3, 1999 Bouvier et al. Mills, M. S. et al. "Application of mixed-mode, solid-phase extrac 5,976,367 11, 1999 Bouvier et al. tion in environmental and clinical chemistry.” Journal of Chroma 6,045,697 4, 2000 Girot et al. tography. 629:11-21 (1993). 6,106,721 8, 2000 Bouvier et al. http://en.wikipedia.org/wilki/Amide Nov. 15, 2007. 6,117,996 9, 2000 Lowe et al. Office Action mailed Aug. 3, 2011, in co-pending U.S. Appl. No. 6,238,565 5, 2001 Hatch 12/855,300. 6,248,798 6, 2001 Slingsby et al. 6,322,695 11, 2001 Lee et al. * cited by examiner U.S. Patent u940MWT-Tuu/6InSTKO U.S. Patent Jun. 12, 2012 Sheet 2 of 2 US 8,197,692 B2 E 8 i O a 8 US 8, 197,692 B2 1. 2 POROUS MATERALS FOR SOLID PHASE compounds, without porogens but in the presence of high EXTRACTION AND CHROMATOGRAPHY concentration of inorganic salts such as ammonium sulfate. AND PROCESSES FOR PREPARATION AND Polymeric monoliths are chemically stable against USE THEREOF strongly alkaline and strongly acidic mobile phases, allowing flexibility in the choice of mobile phase pH. However, the REFERENCE TO RELATED APPLICATIONS prior art monoliths do not necessarily provide the unique selectivities and advantages that are needed for a variety of The present application is a continuation of U.S. patent chromatographic applications, in particular SPE applica application Ser. No. 10/782,397, filed Feb. 18, 2004, now tions. U.S. Pat. No. 7,731.844, which is a continuation-in-part of 10 U.S. application Ser. No. 10/169,546 now U.S. Pat. No. 7.232,520, which entered the U.S. national stage on Jan. 16, SUMMARY OF THE INVENTION 2003, as the U.S. national phase application of PCT interna tional application No. PCT/US99/13241, filed on Jun. 10, 1999, which claims the benefit of U.S. provisional application 15 The invention is directed to novel porous materials that are Ser. No. 60/089,153, filed on Jun. 12, 1998. The present useful in chromatographic processes, e.g., Solid phase extrac application also contains subject matter that is related to that tion, and that provide a number of advantages. Such advan disclosed and claimed in U.S. application Ser. No. 09/505, tages include Superior wetting characteristics, selective cap 456, filed on Feb. 11, 2000, now U.S. Pat. No. 6,322,695, ture of analytes of interest, and non-retention of interfering which is a continuation-in-part of PCT international applica analytes. The invention also provides novel porous materials tion No. PCT/US99/13241, filed on Jun. 10, 1999, which that overcome the problems of particle passage through frits. claims priority to U.S. provisional application Ser. No. Thus, in a first aspect, the invention provides a porous 60/089,153, filed on Jun. 12, 1998. The disclosures of all the material comprising a copolymer of at least one hydrophobic aforementioned patent applications and the aforementioned monomerand at least one hydrophilic monomer, wherein said patent are incorporated herein in their entireties by this ref 25 copolymer further comprises at least one ion-exchange func CCC. tional moiety selected from the group consisting of an acyclic BACKGROUND OF THE INVENTION secondary amine exclusive of polyethylenimine, a cyclic ter tiary amine, a Substituted acyclic amine, and a substituted Solid phase extraction (SPE) is a chromatographic tech 30 cyclic amine. nique that is widely used, e.g., for preconcentration and In a second aspect, the invention provides a copolymer cleanup of analytical samples, for purification of various having the formula I: chemicals, and for removal of toxic or valuable Substances from aqueous solutions. SPE is usually performed using a column or cartridge containing an appropriate material or 35 sorbent. SPE procedures have been developed using sorbents and salts thereof, that can interact with analytes by hydrophobic, ion-exchange, wherein the order of repeat units A, B and C may be chelation, sorption, and other mechanisms, to bind and random, block, or a combination of random and block; remove the analytes from fluids. wherein Because different SPE applications can require different 40 sorbents, there is a need for sorbents with novel properties that have unique selectivities. These include Superior wetting characteristics, selective capture of analytes of interest, and 1 (p + n) 100 non-retention of interfering analytes. Sorbents comprising or < r < 45 porous particles having the aforementioned properties are and described in WO99/64480 and in U.S.
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