Biocompatible Monomer and Polymer Composition

Biocompatible Monomer and Polymer Composition

US5328687
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A biocompatible monomer composition contains (A) at least one monomer of the formula:

CHR=CXY

wherein X and Y are each strong electron withdrawing groups, and R is H or, provided that X and Y are both cyano groups, a C1-C4 alkyl group; and (B) an effective amount of at least one biocompatible agent effective to reduce active formaldehyde concentration levels, preferably an alpha-cyanoacrylate. The formaldehyde scavenger compound may be in microencapsulated form. the composition can be applied to a variety of materials and is particularly suitable as in vivo tissue adhesive. A method of joining together in vivo two surfaces, e.g., body tissues, includes (a) applying to at least one of the surfaces a composition containing 1) at least one monomer, preferably an alpha-cyanoacrlylate, which forms a polymer whose in vivo biodegradation produces formaldehyde; and 2) an effective amount of at least one biocompatible agent effective to reduce active formaldehyde concentration levels, preferably a formaldehyde scavenger; and (b) maintaining the surfaces in contact until the composition polymerizes.

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United States Patent [191 Leung et al. ||||l|lllllllllllIllll||l||llllllllllllllllllllllllllllllllllllllllllllllll US005328687A [11] Patent Number: [45] Date of Patent: 5,328,687 [54] BIOCOMPATIBLE MONOMER AND POLYMER COMPOSITIONS [75] Inventors: Jeffrey C. Leung; Jeffrey G. Clark, both of Raleigh, N.C. [73] Assignee: Tri-Point Medical L.P., Raleigh, N.C. [21] App]. No.: 40,618 [22] Filed: Mar. 31, 1993 [51] Int. Cl.5 ..................... .. A61K 31/74; A61K 9/14; C08F 120/44; C08F 222/34 [52] U.S. Cl. ............................... .. 424/78.35; 424/423; 424/451; 424/489; 514/963 [58] Field of Search ................... .. 424/423, 78.35, 451, 424/489; 526/297, 300, 341; 606/228; 514/963; 264/4.1, 4.3, 4.6 [56] References Cited U.S. PATENT DOCUMENTS 2,721,858 10/1955 Joyner et al. ..................... .. 528/267 2,765,332 10/1956 Coover, Jr. et al. ..... .. .. 558/307 3,254,111 5/1966 Hawkins et al. 558/381 3,527,841 9/1970 Wicker, Jr. et al. 528/354 3,554,990 1/1971 Quinn et al. .......... .. 428/522 3,559,652 2/1971 Banitt et al. ................... .. 606/214 3,564,078 2/1971 Wicker, Jr. et al. 424/78.06 3,591,676 7/1971 Hawkins et al. ........... .. 424/78.06 3,722,599 3/1973 Robertson et al. ........... .. 606/214 3,909,408 9/1975 Ishida et al. ........... .. 210/757 3,940,362 2/1976 Overhults .......................... .. 523/116 3,995,641 12/1976 Kronenthal et al. .............. .. 606/214 4,127,382 11/1978 Perry ..................................... .. 8/181 4,364,876 12/1982 Kimura et al. 558/443 4,524,093 6/1985 Devry ....... .. . 427/389.9 4,675,273 6/1987 Woods et al. . . . . . . . . . . . . . .. 430/325 4,804,691 2/1989 English et al. .................... .. 523/118 5,112,652 5/1992 Greene .............................. .. 427/342 FOREIGN PATENT DOCUMENTS 1162904 2/1984 Canada. 0138448 4/1985 European Pat. Off. . OTHER PUBLICATIONS “Methods of Abating Residual Formaldehyde in Indus- trial Resins”, EPO Applied Technology Series vol. 10. “Synthesis and Degradation of Poly(all
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