US 5,607,687 AGranted

Polymer blends containing absorbable polyoxaesters

AssigneeEthicon, Inc.

InventorsRao S. Bezwada, Dennis D. Jamiolkowski

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Abstract

The present invention describes a new aliphatic polyoxaesters and blends thereof that may be used to produce surgical devices such as sutures, sutures with attached needles, molded devices, and the like. The invention also contemplates a process for producing these polyesters. The aliphatic polyoxaesters of the present invention have a first divalent repeating unit of formula I: [O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1l)(R.sub.2)--C(O)- -] I and a second repeating unit selected from the group of formulas consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, and III ([--O--R.sub.5 --C(O)].sub.P --O--).sub.L G XI and combinations thereof. These aliphatic polyoxaesters may be blended with other polymers which are preferably biocompatable.

Claims22

Dependent claims

A polymer blend comprising an aliphatic polyoxaesters having a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1) (R.sub.2)--O--(R.sub.3)--O--C(R.sub.1) (R.sub.2)--C(O)--] I
and a second repeating unit selected from the group of formulas consisting of:
[--O--R.sub.4 --]A, II
[--O--R.sub.5 --C(O)--].sub.B, and III
([--O--R.sub.5 C(O)].sub.P --O--).sub.L G XI
and combinations thereof, wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit containing from 2 to 12 carbon atoms or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 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 case E will be an integer from 2 to 12;
R.sub.4 is an alkylene unit containing from 2 to 8 carbon atoms;
A is an integer in the range of from 1 to 2,000;
R.sub.5 is selected from the group consisting of --C(R.sub.6), --(R.sub.7)--, --(CH.sub.2).sub.3 --O--, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --, --CR.sub.8 H--CH.sub.2 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.F --O--C(O)-- and --(CH.sub.2).sub.F C(O)--CH.sub.2 --;
R.sub.6 and R.sub.7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is hydrogen or methyl;
F is an integer in the range of from 2 to 6;
B is an integer in the range of from 1 to n such that the number average molecular weight of formula III is less than about 200,000;
P is an integer in the range of from 1 to m such that the number average molecular weight of formula XI is less than about 1,000,000;
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;
and L is an integer from about 1 to about 200;
and
a second polymer selected from the group consisting of homopolymer and copolymer of lactone type polymers with the repeating units described by formulas III and XI, aliphatic polyurethanes, polyether polyurethanes, polyester polyurethanes, polyethylene copolymers, polyamides, polyvinyl alcohols, poly(ethylene oxide), polypropylene oxide, polyethylene glycol, polypropylene glycol, polytetramethylene oxide, polyvinyl pyrrolidone, polyacrylamide, poly(hydroxy ethyl acrylate), poly(hydroxyethyl methacrylate) and combinations thereof.

18 more elements

A device made from a polymer blend comprising an aliphatic polyoxaesters comprising a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1) (R.sub.2)--C(O)--] I
and a second repeating unit selected from the group of formulas consisting of:
[--O--R.sub.4 --].sub.A, II
[--O--R.sub.5 --C (O)--].sub.B, and III
([--O--R.sub.5 --C(O)].sub.P --O--).sub.L G XI
and combinations thereof, wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit containing from 2 to 12 carbon atoms or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 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 case E will be an integer from 2 to 12;
R.sub.4 is an alkylene unit containing from 2 to 8 carbon atoms;
A is an integer in the range of from 1 to 2,000;
R.sub.5 is selected from the group consisting of --C(.sub.6) (R.sub.7)--, --(CH.sub.2).sub.3 --O--, --CH.sub.2 --CH.sub.2 --O--CH.sub.2, --CR.sub.8 H--CH.sub.2 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.F --O--C(O)-- and --(CH.sub.2).sub.F --C(O)--CH.sub.2 --;
R.sub.6 and R.sub.7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is hydrogen or methyl;
F is an integer in the range of from 2 to 6;
B is an integer in the range of from 1 to n such that the number average molecular weight of formula III is less than about 200,000;
P is an integer in the range of from 1 to m such that the number average molecular weight of formula XI is less than about 1,000,000;
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;
and L is an integer from about 1 to about 200;
and a second polymer selected from the group consisting of homopolymer and copolymer of lactone type polymers with the repeating units described by formulas III and XI, aliphatic polyurethanes, polyether polyurethanes, polyester polyurethanes, polyethylene copolymers, polyamides, polyvinyl alcohols, poly(ethylene oxide), polypropylene oxide, polyethylene glycol, polypropylene glycol, polytetramethylene oxide, polyvinyl pyrrolidone, polyacrylamide, poly(hydroxy ethyl acrylate), poly(hydroxyethyl methacrylate) and combinations thereof.

17 more elements

A device coated with a polymer blend comprising an aliphatic polyoxaesters having a first divalent repeating unit of formula I:

[O----C (O)--C(R.sub.1) (R.sub.2)--O--(R.sub.3)--O--C(R.sub.1) (R.sub.2)--C(O)--.sub.] I
and a second repeating unit selected from the group of formulas consisting of:
[--O--R.sub.4 --].sub.A, II
[--O--R.sub.5 --C(O)--].sub.B, and III
([--O--R.sub.5 --C(O)].sub.P --O--).sub.L G XI
and combinations thereof, wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit containing from 2 to 12 carbon atoms or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 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 case E will be an integer from 2 to 12;
R.sub.4 is an alkylene unit containing from 2 to 8 carbon atoms;
A is an integer in the range of from 1 to 2,000;
R.sub.5 is selected from the group consisting of --C(R.sub.6) (R.sub.7)--, --(CH.sub.2).sub.3 --O--, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --, --CR.sub.8 H--CH.sub.2 --, --(CH.sub.2 .sub.5 --, --(CH.sub.2).sub.F --O--C(O)-- and --(CH.sub.2) .sub.F --C(O)--CH.sub.2 --;
R.sub.6 and R.sub.7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is hydrogen or methyl;
F is an integer in the range of from 2 to 6;
B is an integer in the range of from 1 to n such that the number average molecular weight of formula III is less than about 200,000;
P is an integer in the range of from 1 to m such that the number average molecular weight of formula XI is less than about 1,000,000;
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;
and L is an integer from about 1 to about 200;
and a second polymer selected from the group consisting of homopolymer and copolymer of lactone type polymers with the repeating units described by formulas III and XI, aliphatic polyurethanes, polyether polyurethanes, polyester polyurethanes, polyethylene copolymers, polyamides, polyvinyl alcohols, poly(ethylene oxide), polypropylene oxide, polyethylene glycol, polypropylene glycol, polytetramethylene oxide, polyvinyl pyrrolidone, polyacrylamide, poly(hydroxy ethyl acrylate), poly(hydroxyethyl methacrylate) and combinations thereof wherein the inherent viscosity of the polymer blend is in the range of from about 0.05 to about 2.0 deciliters per gram (dl/g) as measured in a 0.1 g/dl solution of hexafluoroisopropanol (HFIP) at 25.degree. C.

17 more elements

A drug delivery matrix comprising a drug and a polymer blend containing an aliphatic polyoxaester having a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1) (R.sub.2)--O--(R.sub.3)--O--C(R.sub.1) (R.sub.2)--C(O)--] I
and a second repeating unit selected from the group of formulas consisting of:
[--O--R.sub.4 --].sub.A, II
[--O--R.sub.5 --C(O)--].sub.B, and III
([--O--R.sub.5 C(O)].sub.P --O--).sub.L G XI
and combinations thereof, wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit containing from 2 to 12 carbon atoms or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 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 case E will be an integer from 2 to 12;
R.sub.4 is an alkylene unit containing from 2 to 8 carbon atoms;
A is an integer in the range of from 1 to 2,000;
R.sub.5 is selected from the group consisting of --C(R.sub.6) (R.sub.7)--, --(CH.sub.2).sub.3 --O--, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --, --CR.sub.8 H--CH.sub.2 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.F --O--C(O)-- and --(CH.sub.2).sub.F --C(O)--CH.sub.2 --;
R.sub.6 and
R.sub.7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is hydrogen or methyl;
F is an integer in the range of from 2 to 6;
B is an integer in the range of from 1 to n such that the number average molecular weight of formula III is less than about 200,000;
P is an integer in the range of from 1 to m such that the number average molecular weight of formula XI is less than about 1,000,000;
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;
and L is an integer from about 1 to about 200;
and
a second polymer selected from the group consisting of homopolymer and copolymer of lactone type polymers with the repeating units described by formulas III and XI, aliphatic polyurethanes, polyether polyurethanes, polyester polyurethanes, polyethylene copolymers, polyamides, polyvinyl alcohols, poly(ethylene oxide), polypropylene oxide, polyethylene glycol, polypropylene glycol, polytetramethylene oxide, polyvinyl pyrrolidone, polyacrylamide, poly(hydroxy ethyl acrylate), poly(hydroxyethyl methacrylate) and combinations thereof.

19 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/611,119Filed 5 Mar 1996 · continuation in part
Priority: 6 Mar 1995
Granted: 4 Mar 1997
Term ends: Not estimatedThe source records don’t support an estimate.

Classification38 codes

C08L 67/025
Polyesters derived from dicarboxylic acids and dihydroxy compounds: containing polyether sequences
A61K 9/204
Obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers:…
A61L 15/225
Containing macromolecular materials: mixtures of macromolecular compounds
A61L 15/26
Containing macromolecular materials: macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated…