BIOABSORBABLE BLOCK COPOLYMER
A bioabsorbable polyurethane block copolymer with having hard and soft segments is formed by the reaction between a diisocyanate such as lysine ethyl ester diisocyanate and a mixture of (i) an aromatic amide or an amino acid derivative and (ii) a polyether glycol and/or an absorbable elastomeric polymer derived from the reaction between dialkylene glycol and a cyclic bioabsorbable monomer such as trimethylene carbonate, caprolactone, or dioxanone.
1 . A bioabsorbable block copolymer possessing hard and soft segments comprising the reaction product of:
a) a biodegradable and biocompatible diisocyanate; and
b) a mixture of
i) an aromatic compound having molecular formula (I):
wherein X is oxygen or sulfur, and Z is selected from the group consisting of an alkyl moiety having from 1 to about 6 carbon atoms, an aralkyl moiety having from 7 to about 12 carbon atoms, a moiety having molecular formula (II):
a moiety having molecular formula (III):
and a moiety having molecular formula (IV):
—R 3 —CH(NHR 5 )—C(O)O—R 4 — (IV)
wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of an alkyl moiety having from 1 to about 6 carbon atoms and an aralkyl group having from 7 to about 10 carbon atoms, R 5 is hydrogen or an alkyl group having from 1 to about 6 carbon atoms, and R 6 is an alkyl group of from about 1 to about 18 carbon atoms; and
ii) an aliphatic polyether glycol and/or an absorbable elastomeric polymer derived from the reaction between dialkylene glycol and a cyclic bioabsorbable monomer including at least one of trimethylene carbonate, dioxanone or caprolactone.
2 . The bioabsorbable block copolymer of claim 1 wherein the biodegradable and biocompatible diisocyanate is a lysine derivative.
3 . The bioabsorbable block copolymer of claim 2 wherein the lysine derivative is lysine ethyl ester diisocyanate.
4 . The bioabsorbable block copolymer of claim 1 wherein R 1 and R 2 are each —CH 2 CH 2 —.
5 . The bioabsorbable block copolymer of claim 1 wherein the polyalkylene glycol is selected from the group consisting of polyethylene glycol and polypropylene glycol.
6 . The bioabsorbable block copolymer of claim 1 wherein the absorbable elastomeric polymer is derived from the reaction between diethylene glycol and trimethylene carbonate.
7 . The bioabsorbable block copolymer of claim 1 further containing a medically useful substance selected from the group consisting of antimicrobial agents and tissue growth promoters.
8 . A surgical device fabricated from the block copolymer of claim 1 .
9 . The surgical device of claim 8 wherein the surgical device is selected from the group consisting of a surgical suture, a bone pin, a surgical clip and a two-part surgical fastener.
10 . A bioabsorbable block copolymer possessing alternating hard and soft segments comprising the reaction product of:
a) a biodegradable and biocompatible diisocyanate; and
b) a mixture of
i) an amino acid derivative having molecular formula (V):
H-[—X—R 7 —CH(NHR 8 )—C(O)-] n —X—R 7 —CH(NHR 8 )—C(O)—Y—R 9 —OH (V)
wherein X is oxygen or sulfur, R 7 and R 9 are independently selected from an alkyl moiety having from 1 to about 6 carbon atoms, aryl, or alkaryl having from 7 to about 12 carbon atoms; R 8 is hydrogen or an alkyl moiety having from 1 to about 6 carbon atoms, Y is oxygen or —NH—, and n is an integer of from 1 to about 10; and
ii) an aliphatic polyether glycol and/or an absorbable elastomeric polymer derived from the reaction between dialkylene glycol and a cyclic bioabsorbable monomer including at least one of trimethylene carbonate, dioxanone or caprolactone.
11 . The bioabsorbable block copolymer of claim 10 wherein the biodegradable and biocompatible diisocyanate is a lysine derivative.
12 . The bioabsorbable block copolymer of claim 11 wherein the lysine derivative is lysine ethyl ester diisocyanate.
13 . The bioabsorbable block copolymer of claim 10 wherein the polyalkylene glycol is selected from the group consisting of polyethylene glycol and polypropylene glycol.
14 . The bioabsorbable block copolymer of claim 10 wherein the absorbable elastomeric polymer is derived from the reaction between diethylene glycol and trimethylene carbonate.
15 . The bioabsorbable block copolymer of claim 10 further containing a medically useful substance selected from the group consisting of antimicrobial agents and tissue growth promoters.
16 . A surgical device fabricated from the block copolymer of claim 10 .
17 . The surgical device of claim 16 wherein the surgical device is selected from the group consisting of a surgical suture, a bone pin, a surgical clip and a two-part surgical fastener.