US 5,703,200 A · Absorbable copolymers and blends of 6,6-dialkyl-1,4-dioxepan-2-one and its cyclic dimer

Abstract

This invention provides various copolymers comprising a first repeating unit of the chemical formula: ##STR1## in which R.sub.1 and/or R.sub.2 are alkyl groups and a second repeating units generally having the chemical formula: ##STR2## and combinations of two or more thereof wherein R is a hydrogen atom or a methyl group and the first repeating unit is less than 45 weight percent of the total weight of the copolymer. This invention also relates to use of these copolymers in the fabrication of absorbable surgical devices such as sutures and as coatings for medical devices. Additionally, described are blends and polyoxaesters containing the first repeating unit.

Claims62

Dependent claims

A copolymer comprising a first repeating unit of the chemical formula:

##STR9## in which R.sub.1 and R.sub.2 are independently alkyl groups selected from the group consisting of methyl, ethyl and propyl groups and a second repeating unit is generated from a monomer selected from the group of glycolic acid, lactic acid, glycolide, lactide (1, d, dl and meso), 3-methyl-1,4-dioxan-2,5-dione, 3,3-diethyl-1,4-dioxan-2,5-one, 1,4-dioxan-2-one, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one, delta-valerolactone, epsilon-decalactone, pivalolactone, gamma-butyrolactone, ethylene carbonate, 1,3-dioxan-2-one, 4,4-dimethyl-1,3-dioxan-2-one, epsilon-caprolactone and combinations thereof and the first repeating unit is less than 45 weight percent of the total weight of the copolymer.

A surgical device having at least a part thereof made from a polymeric blend composed of at least one first polymer selected from the group consisting of homopolymers and copolymers (including segmented block copolymers and graft copolymers) prepared from monomers selected from the group consisting of glycolic acid, lactic acid, glycolide, L-lactide, D-lactide, D,L-lactide, meso-lactide, 1,4-dioxan-2-one, 1,3-dioxan-2-one, 4,4-dimethyl-1,3-dioxan-2-one, .epsilon.-caprolactone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one and combinations thereof;

and a second polymer having a first repeating unit of the chemical formula:
##STR17## in which R.sub.1 and R.sub.2 are independently alkyl groups selected from the group consisting of methyl, ethyl and propyl groups and optionally a second repeating unit is generated from a monomer selected from the group of glycolic acid, lactic acid, glycolide, lactide (1, d, dl and meso), 3-methyl-1,4-dioxan-2,5-dione, 3,3-diethyl-1,4-dioxan-2,5-one, 1,4-dioxan-2-one, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one, delta-valerolactone, epsilon-decalactone, pivalolactone, gamma-butyrolactone, ethylene carbonate, 1,3-dioxan-2-one, 4,4-dimethyl-1,3-dioxan-2-one, epsilon-caprolactone and combinations thereof and the first repeating unit is less than 45 weight percent of the total weight of the copolymer.

A polymeric blend composed of at least one first polymer selected from homopolymers and copolymers (including segmented block copolymers and graft copolymers) prepared from monomers selected from the group consisting of glycolic acid, lactic acid, glycolide, L-lactide, D-lactide, D,L-lactide, meso-lactide, 1,4-dioxan-2-one, 1,3-dioxan-2-one, 4,4-dimethyl-1,3-dioxan-2-one, .epsilon.-caprolactone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one and combinations thereof;

and a second polymer having a first repeating unit of the chemical formula:
##STR19## in which R.sub.1 and R.sub.2 are independently alkyl groups selected from the group consisting of methyl, ethyl and propyl groups and a second repeating unit is generated from a monomer selected from the group of glycolic acid, lactic acid, glycolide, lactide (1, d, dl and meso), 3-methyl-1,4-dioxan-2,5-dione, 3,3-diethyl-1,4-dioxan-2,5-one, 1,4-dioxan-2-one, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one, delta-valerolactone, epsilon-decalactone, pivalolactone, gamma-butyrolactone, ethylene carbonate, 1,3-dioxan-2-one, 4,4-dimethyl-1,3-dioxan-2-one, epsilon-caprolactone and combinations thereof and the first repeating unit is less than 45 weight percent of the total weight of the copolymer.

A polyoxaester having a formula selected from the group consisting of

(--C(O)--C(R.sub.3) (R.sub.4)--O--R.sub.5 --O--C(R.sub.3) (R.sub.4)--C(O)--(O--R.sub.6).sub.A --O).sub.S (Q).sub.B !.sub.WXII
and
(--C(O)--C(R.sub.3) (R.sub.4)--O--R.sub.5 --O--C(R.sub.3) (R.sub.4)--C(O)--(O--R.sub.6).sub.A --O).sub.S (Q!.sub.P --O--).sub.L G!.sub.W XIII
wherein R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen or an alkyl group containing from 1 to 8 carbon atoms and R.sub.5 is an alkylene containing from 2 to 12 carbon atoms or is an oxyaIkylene group of the following formula:
--(CH.sub.2)C--O--!.sub.D --(CH.sub.2).sub.E IV
wherein C is an integer in the range of from about 2 to about 5, D is an integer in the range of from about 0 to about 2,000, and E is an integer in the range of from about 2 to about 5 except when D is zero in which event E is an integer from 1 to 12;
R.sub.6 is an alkylene unit containing from 2 to 8 methylene units;
A is an integer in the range of from 1 to about 2,000;
B is an integer in the range of from 1 to n such that the number average molecular weight of Q is less than about 100,000;
Q is an aliphatic polyester having at least a first repeating unit of the chemical formula:
##STR21## wherein R.sub.1 and R.sub.2 are independently alkyl groups selected from the group consisting of methyl, ethyl and propyl groups;
P is an integer in the range of from 1 to m such that the number average molecular weight of the formula:
(Q!.sub.P --O--).sub.L G
is less than about 100,000;
G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl groups of an alcohol previously containing from 1 to about 200 hydroxyl groups;
L is an integer from about 1 to about 200;
and S is an integer in the range of from about 1 to about 1,000;
and W is an integer in the range of from about 1 to about 1,000.

15 more elements

Dependencies are inferred from the claim text.

Absorbable copolymers and blends of 6,6-dialkyl-1,4-dioxepan-2-one and its cyclic dimer

Life of this patent

Absorbable copolymers and blends of 6,6-dialkyl-1,4-dioxepan-2-one and its cyclic dimer

Life of this patent

Abstract

Claims62