US5575997A
Expired / Lapsed
US
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Biocompatible monomer and polymer compositions
Assignee: Ethicon Inc
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Filing: 1995-06-05
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Granted: 1996-11-19
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Expires: 2015-06-05
Abstract
Abstract 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 C 1 -C 4 alkyl group; and (B) an effective amount of at least one biocompatible agent effective to reduce active formaldehyde concentration levels, preferably a formaldehyde scavenger compound. The monomer is preferably an alpha-cyanoacrylate. The formaldehyde scavenger compound may be in microencapsulated or non-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-cyanoacrylate, 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.
Inventors
- 👤 Jeffrey C. Leung
- 👤 Jeffrey G. Clark
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 23:50
CPC Classifications
A; A61; A61L; A61L24/00; A61L24/04; A61L24/06; C; C09; C09J; C09J4/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
90 words
A method of dressing living tissue, comprising (a) applying to said living tissue a composition comprising 1) at least one monomer 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; and (b) allowing the composition to polymerize, wherein the at least one monomer has the formula: CHR═CXY wherein R is H, C 1 -C 4 alkyl group, or --CH═CH 2 group, and X and Y are both strong electron withdrawing groups.
Claim 2
Independent Claim
90 words
A method of dressing living tissue, comprising (a) applying to said living tissue a composition comprising 1) at least one monomer 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; and (b) allowing the composition to polymerize, wherein the at least one monomer has the formula: CHR═CXY wherein R is H, C 1 -C 4 alkyl group, or --CH═CH 2 group, and X and Y are both strong electron withdrawing groups.
Claim 3
Independent Claim
84 words
A method of dressing living tissue, comprising (a) applying to said living tissue a composition comprising 1) at least one monomer which forms a polymer whose in vivo biodegradation produces formaldehyde; and 2) an effective amount of at least one formaldehyde scavenger compound; and (b) allowing the composition to polymerize, wherein the at least one monomer has the formula: CHR═CXY wherein R is H, C 1 -C 4 alkyl group, or --CH═CH 2 group, and X and Y are both strong electron withdrawing groups.
Claim 4
Independent Claim
84 words
A method of dressing living tissue, comprising (a) applying to said living tissue a composition comprising 1) at least one monomer which forms a polymer whose in vivo biodegradation produces formaldehyde; and 2) an effective amount of at least one formaldehyde scavenger compound; and (b) allowing the composition to polymerize, wherein the at least one monomer has the formula: CHR═CXY wherein R is H, C 1 -C 4 alkyl group, or --CH═CH 2 group, and X and Y are both strong electron withdrawing groups.
Claim 5
Dependent Claim
78 words
A method according to claim 1, wherein the at least one monomer is an alpha-cyanoacrylate, a vinylidene cyanide, a C 1 -C 4 alkyl homolog of a vinylidene cyanide, a dialkyl methylene malonate, an acylacrylonitrile, a vinyl sulfinate or vinyl sulfonate of the formula CH 2 ═CX'Y' where X' is --SO 2 R' or --SO 3 R' and Y' is --CN, --COOR, --COCH 3 , --SO 2 R' or --SO 3 R' and R' is H or hydrocarbyl.
Claim 6
Dependent Claim
15 words
A method according to claim 3, wherein the at least one monomer is an alpha-cyanoacrylate.
Claim 7
Dependent Claim
100 words
A method according to claim 4, wherein the alpha-cyanoacrylate monomer has the formula ##STR6## wherein R 2 is hydrogen and R 3 is a hydrocarbyl or substituted hydrocarbyl group; a group having the formula --R 4 --O--R 5 --O--R 6 wherein R 4 is a 1,2-alkylene group having 2-4 carbon atoms, R 5 is an alkylene group having 2-4 carbon atoms, and R 6 is an alkyl group, having 1-6 carbon atoms; or a group having the formula ##STR7## wherein R 7 is --CH 2 --, ##STR8## or --C(CH 3 ) 2 -- and R 8 is an organic radical.
Claim 8
Dependent Claim
98 words
A method according to claim 5, wherein R 3 is a hydrocarbyl or substituted hydrocarbyl group, selected from the group consisting of straight chain or branched chain alkyl groups having 1-16 carbon atoms; straight chain or branched chain C 1-16 alkyl groups substituted with an acyloxy group, a haloalkyl group, an alkoxy group, a halogen atom, a cyano group, or a haloalkyl group; straight chain or branched chain alkenyl groups having 2 to 16 carbon atoms; straight chain or branched chain alkynyl groups having 2 to 12 carbon atoms; cycloalkyl groups; aralkyl groups; alkylaryl groups; and aryl groups.
Claim 9
Dependent Claim
56 words
A method according to claim 6, wherein R 3 is an alkyl group having 1-6 carbon atoms or a group having the formula --AOR 9 wherein A is a divalent straight or branched chain alkylene or oxyalkylene radical having 2-8 carbon atoms, and R 9 is a straight or branched alkyl radical having 1-8 carbon atoms.
Claim 10
Dependent Claim
24 words
A method according to claim 7, wherein the alpha-cyanoacrylate is methyl cyanoacrylate, butyl cyanoacrylate, octyl cyanoacrylate, 1-methoxy-2-propyl cyanoacrylate, 2-butoxy ethyl cyanoacrylate, or isopropoxy-ethyl cyanoacrylate.
Claim 11
Dependent Claim
16 words
A method according to claim 1, wherein the at least one biocompatible agent is sodium bisulfite.
Claim 12
Dependent Claim
24 words
A method according to claim 1, wherein the at least one biocompatible agent effective to reduce active formaldehyde concentration levels is in microencapsulated form.
Claim 13
Dependent Claim
39 words
A method according to claim 1, wherein the at least one biocompatible agent effective to reduce active formaldehyde concentration levels is microencapsulated with a coating polymer which undergoes in vivo bioerosion and which has a low inherent moisture content.
Claim 14
Dependent Claim
75 words
A method according to claim 11, wherein the at least one biocompatible agent effective to reduce active formaldehyde concentration levels is microencapsulated with a coating material selected from the group consisting of polyglycolic acid, polylactic acid, copolymers of polyglycolic acid and polylactic acid, polycaprolactone, poly-β-hydroxybutyrate, copolymers of epsilon-caprolactone and delta-valerolactone, copolymers of epsilon-caprolactone and DL-dilactide, polyester hydrogels, polyvinylpyrrolidone, polyamides, gelatin, albumin, proteins, collagen, poly(orthoesters), poly(anhydrides) poly (alkyl-2-cyanoacrylates), poly(dihydropyrans), poly(acetals), poly(phosphazenes), poly(urethanes), poly(dioxinones), cellulose, and starches.
Claim 15
Dependent Claim
37 words
A method according to claim 1, wherein said living tissue comprises small blood vessels, and said method stems flow of blood from said small blood vessels by applying to said vessels a hemostatic agent comprising said composition.
Claim 16
Dependent Claim
13 words
A method according to claim 1, wherein said living tissue has been burned.
Claim 17
Dependent Claim
15 words
A method according to claim 1, wherein said living tissue is exposed in a wound.
Claim 18
Dependent Claim
47 words
A method according to claim 1, wherein the at least one monomer has 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 C 1 -C 4 alkyl group.
Claim 19
Dependent Claim
157 words
A method according to claim 5, wherein R 8 is selected from the group consisting of straight chain or branched chain alkyl groups having 1 to 8 carbon atoms; straight chain or branched chain C 1-8 alkyl groups substituted with a halo group or an oxy group; straight chain or branched chain alkenyl groups having 2 to 8 carbon atoms; straight chain or branched chain C 2-8 alkenyl groups substituted with a halo group or an oxy group; straight chain or branched chain alkynyl groups having 2 to 8 carbon atoms; straight chain or branched chain C 2-8 alkynyl groups substituted with a halo group or an oxy group; cycloaliphatic groups having 3 to 12 carbon atoms; C 3-12 cycloaliphatic groups substituted with a halo group or an oxy group; aryl groups; aryl groups substituted with a halo group or an oxy group; aralkyl groups; and aralkyl groups substituted with a halo group or an oxy group.
References Cited (Backward Citations)
US2765332A
Cited
US2721858A
Cited
US3223083A
Cited
US3254111A
Cited
US3667472A
Cited
US3759264A
Cited
GB1196049A
Cited
US3722599A
Cited
US3527841A
Cited
US3564078A
Cited
US3554990A
Cited
US3559652A
Cited
US3591676A
Cited
US3909408A
Cited
US3940362A
Cited
US3995641A
Cited
US4127382A
Cited
US4900303A
Cited
US4364876A
Cited
US4578061A
Cited
CA1162904A
Cited
US4582648A
Cited
EP0138448A2
Cited
US4524093A
Cited
US4675273A
Cited
US4832688A
Cited
US4744364A
Cited
US4890612A
Cited
US4852568A
Cited
US4804691A
Cited
US5053046A
Cited
US5112652A
Cited
US5061274A
Cited
US5021059A
Cited
US5192300A
Cited
US5108421A
Cited
US5275616A
Cited
US5275616B1
Cited
JPH05123329A
Cited
US5221259A
Cited
US5129882A
Cited
US5330446A
Cited
US5192309A
Cited
EP0543499A1
Cited
US5324306A
Cited
US5222974A
Cited
US5282827A
Cited
US5372585A
Cited
US5292332A
Cited
US5370660A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-11-19 | 2000-05-20 | 2000-11-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-11-19 | 2004-05-20 | 2004-11-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-11-19 | 2008-05-20 | 2008-11-19 | $7700.00 | Window Closed / Lapsed |