Patent · US5648088A · A · US
Blends of absorbable polyoxaesters containing amines and/or amide groups
- (11) Publication number
- US5648088A
- (21) Application number
- 08/611,529
- (22) Filing date
- 1996-03-05
- (30) Priority date
- 1995-03-06
- (43) Publication date
- 1997-07-15
- (45) Date of grant
- 1997-07-15
- (51) IPC
- A61K 47/30; A61K 9/20; A61K 9/22; A61L 15/00; A61L 15/22; A61L 15/26; A61L 15/60; A61L 17/10; A61L 27/00; A61L 27/18; A61L 27/52; A61L 29/04; A61L 29/06; A61L 29/14; A61L 31/00; A61L 31/04; A61L 31/06; C08G 63/66; C08G 63/664; C08G 63/672; C08G 69/40; C08G 69/44; C08L 67/00; C08L 67/02; C09D 167/00
- (52) CPC
- C08L Compositions of macromolecular compounds: 67/025, 101/00, 67/00
- A61K Preparations for medical, dental or toiletry purposes: 9/204
- A61L Methods or apparatus for sterilising materials or objects in general; disinfection, sterilisation or deodorisation of air; chemical aspects of bandages, dressings, absorbent pads or surgical articles; materials for bandages, dressings, absorbent pads or surgical articles: 15/225, 15/26, 15/60, 17/105, 27/18, 27/52, 29/049, 29/06, 29/145, 31/041, 31/06
- C08G Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds: 63/66, 63/664, 63/672, 69/40, 69/44
- C09D Coating compositions, e.g. paints, varnishes or lacquers; filling pastes; chemical paint or ink removers; inks; correcting fluids; woodstains; pastes or solids for colouring or printing; use of materials therefor: 167/00
- Y10T Technical subjects covered by former us classification: 428/1352, 428/1355, 428/1362, 428/24, 428/249921, 428/249953, 428/29, 428/2904, 428/2913, 428/2947, 428/31551, 428/31786, 442/2295
- (73) Assignee
- Ethicon Inc
- (72) Inventors
- Rao S. Bezwada; Dennis D. Jamiolkowski
- (54) Title
- Blends of absorbable polyoxaesters containing amines and/or amide groups
- (57) Abstract
The present invention describes aliphatic polyoxaesters containing amines and/or amido groups and blends thereof with other polymers that may be used to produce surgical devices such as sutures, sutures with attached needles, molded devices, and the like. 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.1)(R.sub.2)--C(O)--]I and a second repeating unit of the formula: [--O--R.sub.12 --].sub.u, XVI and optionally a third repeating unit with a formula selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.5 --C(O)].sub.P --O--).sub.L G XI and combinations thereof wherein R 12 contains an internal amine or internal amide group.
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Claims (34)
- An aliphatic polyoxaester 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.12 --].sub.U, XIV wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R 10)--) or amide (--N(R 11)--); R 10 and R 11 are independently hydrogen or an alloil group containing 1 to 8 carbon atoms; and U is an integer in the range of from 1 to about 2,000.
- The aliphatic polyoxacster of claim 1 wherein the aliphatic polyoxaester additionally contains a third repeating unit selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G and XI and combinations thereof; wherein R 4 is an alkylgne unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to about 2,000; R 5 and R 13 are independently selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)--and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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.
- The aliphatic polyoxaester of claim 1 wherein the polymer has the formula: [--O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)C(O)--(O--R.sub.12).sub.U --].sub.N wherein N is an integer in the range of from about 1 to about 10,000.
- The aliphatic polyoxaester of claim 2 wherein the polymer has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C(R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --O).sub.S (C(O)--R.sub.5 --O).sub.B].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.
- The aliphatic polyoxaester of claim 2 wherein the polymer has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C(R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --O).sub.s([--O--R.sub.13 C(O)].sub.P --O--).sub.L G].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.
- A device made from an aliphatic polyoxaester 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.12 --].sub.U, XIV wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R 10)--) or amide (--N(R 11); R 10 and R 11 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; and U is an integer in the rage of from 1 to about 2,000.
- The device of claim 6 wherein the aliphatic polyoxaester additionally contains a third repeating unit selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G and XI combinations thereof; wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to about 2,000; R 5 and R 13 are independently selected from the group consisting of --C(R 6 (R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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 offorrrtula 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.
- The device of claim 6 wherein the device is an absorbable surgical device.
- The absorbable surgical device of claim 6 wherein the absorbable surgical device is selected from the group consisting of burn dressings, hernia patches, medicated dressings, fascial substitutes, gauze, fabrics, sheets, felts, sponges, gauze bandages, arterial graft, bandages for skin surfaces, suture knot clip, pins, clamps, screws, plates, clips, staples, hooks, buttons, snaps, bone substitutes, intrauterine devices, tubes, surgical instruments, vascular implants, vascular supports, vertebral discs, and artificial skin.
- The absorbable surgical device of claim 6 wherein the device is a filament.
- The filament of claim 10 wherein the filament is attached to a needle.
- The device of claim 6 wherein the aliphatic polyoxaester has the formula: [--O--C(O)--C(R.sub.1)(R.sub.2 --O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --].sub.N wherein N is an integer: in the range of from about 1 to about 10,000.
- The device of claim 6 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C(R.sub.1))(R.sub.2)--C(O)--(O--R.sub.12).sub.u --O).sub.S (C(O)--R.sub.5 --O).sub.B].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.
- The device of claim 6 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--C(R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --O).sub.S ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.
- A device coated with an absorbable coating comprising 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 of formula: [--O--R.sub.12 --].sub.U, XIV and combinations thereof, wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R 10)--) or amide (--N(R 11)--); R 10 and R 11 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; and U is an integer in the range of from 1 to about 2,000; wherein the inherent viscosity of the polyoxaester 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° C.
- The device coated with an absorbable coating of claim 15 wherein the aliphatic polyoxaester additionally contains a third repeating unit selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G and XI combinations thereof wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to about 2,000; R 5 and R 13 are independently selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, (CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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.
- The device coated with an absorbable coating of claim 15 wherein the device is a suture.
- The device coated with an absorbable coating of claim 17 wherein the suture is attached to a needle.
- The device coated with an absorbable coating of claim 15 wherein the aliphatic polyoxaester has the formula: [--O--C(O)--C(R 1)(R 2)--O--(R 3)--O--C(R 1)(R 2)--C(O)--(O--R 12) U --] N wherein N is an integer in the range of from about 1 to about 10,000.
- The device coated with an absorbable coating of claim 15 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R 1)(R 2)--O--R 3 --O--C(R 1)(R 2)--C(O)--(O--R 12) U --O) S (C(O)--R 5 --O) B] W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.
- The device coated with an absorbable coating of claim 15 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R 1 (R 2)--O--R 3 --O--C(R 1)(R 2)--C(O)--(O--R 12) I --O) S ([--O--R 13 --C(O)] P --O--) L G] W wherein S is an integer in the range of from about 1 to 10,000 and W is integer in the range of from about 1 to about 1,000.
- A drug delivery matrix comprising a drug and 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 of formula: [--O--R.sub.12 --].sub.U, XIV wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit or is an oxyalkylene group of the following formula: --[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.B -- 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 12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R 10)--) or amide (--N(R 11)--); R 10 and R 11 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; and U is an integer in the range of from 1 to about 2,000.
- The drug delivery matrix of claim 22 wherein the aliphatic polyoxaester additionally contains a third repeating unit selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G and XI combinations thereof, wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to about 2,000; R 5 and R 13 are independently selected from the group consisting of --C(R 6)(R 7 --, --(CH 2) 3 --O--, --CH 2 CH 2 --O--CH 2 --, --CR 8 --CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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 IH 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.
- The drug delivery matrix of claim 22 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C(R.sub.1)(R.sub.2)--C (O)--(O--R.sub.12).sub.U --O).sub.S(C(O)--R.sub.5 --O).sub.B].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.
- The drug delivery matrix of claim 22 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C (R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --O).sub.S([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.
- An aliphatic polyoxaester 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 two second repeating unit of the formulas: [--O--R.sub.5 --C(O)--].sub.B, and III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XI wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 from 2 to 12; R 5 and R 13 are different and are selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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.
- The aliphatic polyoxaester of claim 26 where additionally present is a third repeating unit of the formula: [--O--R.sub.4 -].sub.A, II wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to 1,000.
- A device made from an aliphatic polyoxaester 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 two second repeating unit selected from the group of formulas consisting of: [--O--R.sub.3 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XI wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 from 2 to 12; R 5 and R 13 are different and are selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, (CH 2) 8 --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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.
- The aliphatic polyoxaester of claim 28 where additionally present is a third repeating unit of the formula: [--O--R.sub.4 --].sub.A, II wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to 1,000.
- A device coated with an absorbable coating comprising 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 two second repeating unit of the formulas: [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XI wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit or is an oxyalkylene group of the following formula: --[(CH.sub.2).sub.C --O--].sub.D --(CH.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 from 2 to 12; R 5 and R 13 are different and are selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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 wherein the inherent viscosity of the polyoxaester is in the range of from about 0.05 to about deciliters per gram (dl/g) as measured in a 0.1 g/dl solution of hexafluoroisopropanol (HFIP) at 25° C.
- The aliphatic polyoxaester of claim 30 where additionally present is a third repeating unit of the formula: [--O--R.sub.4 --].sub.A, II wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to 1,000.
- A drug delivery matrix comprising a drug and 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 two second repeating unit of the formulas: [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 C(O)].sub.P --O--).sub.L G XI wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 from 2 to 12; R 5 and R 13 are different and are selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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 wherein the inherent viscosity of the polyoxaester is in the range of from about 0.05 to about 20 deciliters per gram (dl/g) as measured in a. 0.1 g/dl solution of hexafluoroisopropanol (HFIP) at 25° C.
- The drug delivery matrix of claim 32 wherein the aliphatic polyoxaester has additionally present third repeating unit of the formula: [--O--R.sub.4 --].sub.A, II wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to 1,000.
- The aliphatic polyester of claim 1 wherein D is an integer in the range of from about 0 to about 12.
Description
The present invention is a continuation-in-part of Ser. No. 08/554,011, filed Nov. 6, 1995, now abandoned which is a continuation-in-part of Ser. No. 08/399,308, filed Mar. 6, 1995, now U.S. Pat. No. 5,464,929 (all hereby incorporated herein by reference) and relates to polyoxaesters containing amines and/or amido groups and blends thereof with other polymers and more particularly to surgical products made from polyoxaesters containing amines and/or amido groups and blends thereof with other polymers.
Since Carothers early work in the 1920s and 1930s, aromatic polyester particularly poly(ethylene terephthalate) have become the most commercial important polyesters. The usefulness of these polymers is intimately linked to the stiffening action of the p-phenylene group in the polymer chain. The presence of the p-phenylene group in the backbone of the polymer chain leads to high melting points and good mechanical properties especially for fibers, films and some molded products. In fact poly(ethylene terephthalate) has become the polymer of choice for many common consumer products, such as one and two liter soft drink containers.
Several related polyester resins have been described in U.S. Pat. Nos. 4,440,922, 4,552,948 and 4,963,641 which seek to improve upon the properties of poly(ethylene terephthalate) by replacing terephthalic acid with other related dicarboxylic acids which contain phenylene groups. These polymers are generally designed to reduce the gas permeability of aromatic polyesters.
Citations (8)
- US4689424A
- US4510295A
- US4440922A
- US4546152A
- US4730069A
- US4552948A
- US4963641A
- US5349028A
Record as JSON
{
"publication_number": "US5648088A",
"country": "US",
"kind": "A",
"title": "Blends of absorbable polyoxaesters containing amines and/or amide groups",
"abstract": "The present invention describes aliphatic polyoxaesters containing amines and/or amido groups and blends thereof with other polymers that may be used to produce surgical devices such as sutures, sutures with attached needles, molded devices, and the like. 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.1)(R.sub.2)--C(O)--]I and a second repeating unit of the formula: [--O--R.sub.12 --].sub.u, XVI and optionally a third repeating unit with a formula selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.5 --C(O)].sub.P --O--).sub.L G XI and combinations thereof wherein R 12 contains an internal amine or internal amide group.",
"claims": [
"1. An aliphatic polyoxaester 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.12 --].sub.U, XIV wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R 10)--) or amide (--N(R 11)--); R 10 and R 11 are independently hydrogen or an alloil group containing 1 to 8 carbon atoms; and U is an integer in the range of from 1 to about 2,000.",
"2. The aliphatic polyoxacster of claim 1 wherein the aliphatic polyoxaester additionally contains a third repeating unit selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G and XI and combinations thereof; wherein R 4 is an alkylgne unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to about 2,000; R 5 and R 13 are independently selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)--and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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.",
"3. The aliphatic polyoxaester of claim 1 wherein the polymer has the formula: [--O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)C(O)--(O--R.sub.12).sub.U --].sub.N wherein N is an integer in the range of from about 1 to about 10,000.",
"4. The aliphatic polyoxaester of claim 2 wherein the polymer has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C(R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --O).sub.S (C(O)--R.sub.5 --O).sub.B].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.",
"5. The aliphatic polyoxaester of claim 2 wherein the polymer has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C(R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --O).sub.s([--O--R.sub.13 C(O)].sub.P --O--).sub.L G].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.",
"6. A device made from an aliphatic polyoxaester 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.12 --].sub.U, XIV wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R 10)--) or amide (--N(R 11); R 10 and R 11 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; and U is an integer in the rage of from 1 to about 2,000.",
"7. The device of claim 6 wherein the aliphatic polyoxaester additionally contains a third repeating unit selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G and XI combinations thereof; wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to about 2,000; R 5 and R 13 are independently selected from the group consisting of --C(R 6 (R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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 offorrrtula 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.",
"8. The device of claim 6 wherein the device is an absorbable surgical device.",
"9. The absorbable surgical device of claim 6 wherein the absorbable surgical device is selected from the group consisting of burn dressings, hernia patches, medicated dressings, fascial substitutes, gauze, fabrics, sheets, felts, sponges, gauze bandages, arterial graft, bandages for skin surfaces, suture knot clip, pins, clamps, screws, plates, clips, staples, hooks, buttons, snaps, bone substitutes, intrauterine devices, tubes, surgical instruments, vascular implants, vascular supports, vertebral discs, and artificial skin.",
"10. The absorbable surgical device of claim 6 wherein the device is a filament.",
"11. The filament of claim 10 wherein the filament is attached to a needle.",
"12. The device of claim 6 wherein the aliphatic polyoxaester has the formula: [--O--C(O)--C(R.sub.1)(R.sub.2 --O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --].sub.N wherein N is an integer: in the range of from about 1 to about 10,000.",
"13. The device of claim 6 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C(R.sub.1))(R.sub.2)--C(O)--(O--R.sub.12).sub.u --O).sub.S (C(O)--R.sub.5 --O).sub.B].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.",
"14. The device of claim 6 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--C(R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --O).sub.S ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.",
"15. A device coated with an absorbable coating comprising 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 of formula: [--O--R.sub.12 --].sub.U, XIV and combinations thereof, wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R 10)--) or amide (--N(R 11)--); R 10 and R 11 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; and U is an integer in the range of from 1 to about 2,000; wherein the inherent viscosity of the polyoxaester 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° C.",
"16. The device coated with an absorbable coating of claim 15 wherein the aliphatic polyoxaester additionally contains a third repeating unit selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G and XI combinations thereof wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to about 2,000; R 5 and R 13 are independently selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, (CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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.",
"17. The device coated with an absorbable coating of claim 15 wherein the device is a suture.",
"18. The device coated with an absorbable coating of claim 17 wherein the suture is attached to a needle.",
"19. The device coated with an absorbable coating of claim 15 wherein the aliphatic polyoxaester has the formula: [--O--C(O)--C(R 1)(R 2)--O--(R 3)--O--C(R 1)(R 2)--C(O)--(O--R 12) U --] N wherein N is an integer in the range of from about 1 to about 10,000.",
"20. The device coated with an absorbable coating of claim 15 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R 1)(R 2)--O--R 3 --O--C(R 1)(R 2)--C(O)--(O--R 12) U --O) S (C(O)--R 5 --O) B] W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.",
"21. The device coated with an absorbable coating of claim 15 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R 1 (R 2)--O--R 3 --O--C(R 1)(R 2)--C(O)--(O--R 12) I --O) S ([--O--R 13 --C(O)] P --O--) L G] W wherein S is an integer in the range of from about 1 to 10,000 and W is integer in the range of from about 1 to about 1,000.",
"22. A drug delivery matrix comprising a drug and 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 of formula: [--O--R.sub.12 --].sub.U, XIV wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit or is an oxyalkylene group of the following formula: --[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.B -- 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 12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R 10)--) or amide (--N(R 11)--); R 10 and R 11 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; and U is an integer in the range of from 1 to about 2,000.",
"23. The drug delivery matrix of claim 22 wherein the aliphatic polyoxaester additionally contains a third repeating unit selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G and XI combinations thereof, wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to about 2,000; R 5 and R 13 are independently selected from the group consisting of --C(R 6)(R 7 --, --(CH 2) 3 --O--, --CH 2 CH 2 --O--CH 2 --, --CR 8 --CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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 IH 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.",
"24. The drug delivery matrix of claim 22 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C(R.sub.1)(R.sub.2)--C (O)--(O--R.sub.12).sub.U --O).sub.S(C(O)--R.sub.5 --O).sub.B].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.",
"25. The drug delivery matrix of claim 22 wherein the aliphatic polyoxaester has the formula: [(--C(O)--C(R.sub.1)(R.sub.2)--O--R.sub.3 --O--C (R.sub.1)(R.sub.2)--C(O)--(O--R.sub.12).sub.U --O).sub.S([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G].sub.W wherein S is an integer in the range of from about 1 to 10,000 and W is an integer in the range of from about 1 to about 1,000.",
"26. An aliphatic polyoxaester 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 two second repeating unit of the formulas: [--O--R.sub.5 --C(O)--].sub.B, and III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XI wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 from 2 to 12; R 5 and R 13 are different and are selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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.",
"27. The aliphatic polyoxaester of claim 26 where additionally present is a third repeating unit of the formula: [--O--R.sub.4 -].sub.A, II wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to 1,000.",
"28. A device made from an aliphatic polyoxaester 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 two second repeating unit selected from the group of formulas consisting of: [--O--R.sub.3 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XI wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 from 2 to 12; R 5 and R 13 are different and are selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, (CH 2) 8 --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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.",
"29. The aliphatic polyoxaester of claim 28 where additionally present is a third repeating unit of the formula: [--O--R.sub.4 --].sub.A, II wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to 1,000.",
"30. A device coated with an absorbable coating comprising 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 two second repeating unit of the formulas: [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XI wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit or is an oxyalkylene group of the following formula: --[(CH.sub.2).sub.C --O--].sub.D --(CH.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 from 2 to 12; R 5 and R 13 are different and are selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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 wherein the inherent viscosity of the polyoxaester is in the range of from about 0.05 to about deciliters per gram (dl/g) as measured in a 0.1 g/dl solution of hexafluoroisopropanol (HFIP) at 25° C.",
"31. The aliphatic polyoxaester of claim 30 where additionally present is a third repeating unit of the formula: [--O--R.sub.4 --].sub.A, II wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to 1,000.",
"32. A drug delivery matrix comprising a drug and 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 two second repeating unit of the formulas: [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.13 C(O)].sub.P --O--).sub.L G XI wherein R 1 and R 2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R 3 is an alkylene unit 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 from 2 to 12; R 5 and R 13 are different and are selected from the group consisting of --C(R 6)(R 7)--, --(CH 2) 3 --O--, --CH 2 --CH 2 --O--CH 2 --, --CR 8 H--CH 2 --, --(CH 2) 5 --, --(CH 2) F --O--C(O)-- and --(CH 2) K --C(O)--CH 2 --; R 6 and R 7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R 8 is hydrogen or methyl; F and K are integers 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 wherein the inherent viscosity of the polyoxaester is in the range of from about 0.05 to about 20 deciliters per gram (dl/g) as measured in a. 0.1 g/dl solution of hexafluoroisopropanol (HFIP) at 25° C.",
"33. The drug delivery matrix of claim 32 wherein the aliphatic polyoxaester has additionally present third repeating unit of the formula: [--O--R.sub.4 --].sub.A, II wherein R 4 is an alkylene unit containing from 2 to 8 carbon atoms; A is an integer in the range of from 1 to 1,000.",
"34. The aliphatic polyester of claim 1 wherein D is an integer in the range of from about 0 to about 12."
],
"description_excerpt": "The present invention is a continuation-in-part of Ser. No. 08/554,011, filed Nov. 6, 1995, now abandoned which is a continuation-in-part of Ser. No. 08/399,308, filed Mar. 6, 1995, now U.S. Pat. No. 5,464,929 (all hereby incorporated herein by reference) and relates to polyoxaesters containing amines and/or amido groups and blends thereof with other polymers and more particularly to surgical products made from polyoxaesters containing amines and/or amido groups and blends thereof with other polymers.\n\nSince Carothers early work in the 1920s and 1930s, aromatic polyester particularly poly(ethylene terephthalate) have become the most commercial important polyesters. The usefulness of these polymers is intimately linked to the stiffening action of the p-phenylene group in the polymer chain. The presence of the p-phenylene group in the backbone of the polymer chain leads to high melting points and good mechanical properties especially for fibers, films and some molded products. In fact poly(ethylene terephthalate) has become the polymer of choice for many common consumer products, such as one and two liter soft drink containers.\n\nSeveral related polyester resins have been described in U.S. Pat. Nos. 4,440,922, 4,552,948 and 4,963,641 which seek to improve upon the properties of poly(ethylene terephthalate) by replacing terephthalic acid with other related dicarboxylic acids which contain phenylene groups. These polymers are generally designed to reduce the gas permeability of aromatic polyesters.",
"cpc": [
"C08L 67/025",
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"A61L 15/225",
"A61L 15/26",
"A61L 15/60",
"A61L 17/105",
"A61L 27/18",
"A61L 27/52",
"A61L 29/049",
"A61L 29/06",
"A61L 29/145",
"A61L 31/041",
"A61L 31/06",
"C08G 63/66",
"C08G 63/664",
"C08G 63/672",
"C08G 69/40",
"C08G 69/44",
"C08L 101/00",
"C08L 67/00",
"C09D 167/00",
"Y10T 428/1352",
"Y10T 428/1355",
"Y10T 428/1362",
"Y10T 428/24",
"Y10T 428/249921",
"Y10T 428/249953",
"Y10T 428/29",
"Y10T 428/2904",
"Y10T 428/2913",
"Y10T 428/2947",
"Y10T 428/31551",
"Y10T 428/31786",
"Y10T 442/2295"
],
"ipc": [
"A61K 47/30",
"A61K 9/20",
"A61K 9/22",
"A61L 15/00",
"A61L 15/22",
"A61L 15/26",
"A61L 15/60",
"A61L 17/10",
"A61L 27/00",
"A61L 27/18",
"A61L 27/52",
"A61L 29/04",
"A61L 29/06",
"A61L 29/14",
"A61L 31/00",
"A61L 31/04",
"A61L 31/06",
"C08G 63/66",
"C08G 63/664",
"C08G 63/672",
"C08G 69/40",
"C08G 69/44",
"C08L 67/00",
"C08L 67/02",
"C09D 167/00"
],
"assignees": [
"Ethicon Inc"
],
"inventors": [
"Rao S. Bezwada",
"Dennis D. Jamiolkowski"
],
"filing_date": "1996-03-05",
"publication_date": "1997-07-15",
"grant_date": "1997-07-15",
"priority_date": "1995-03-06",
"application_number": "US-61152996-A",
"family_id": "27070486",
"cited_by_count": 364,
"citations": [
"US4689424A",
"US4510295A",
"US4440922A",
"US4546152A",
"US4730069A",
"US4552948A",
"US4963641A",
"US5349028A"
]
}
Record 6,884 of 8,000 in Patents full text (MLC-0201). Request the full dataset.