Blending containing absorbable polyoxaamides
First Claim
1. A polymer blend comprising an aliphatic polyoxaamide composed of a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[X--C(O)--C(R.sub.1) (R.sub.2)--O--(R.sub.e)--O--C(R.sub.1) (R.sub.2)--C(O)--] Iand a second repeating unit selected from the group of formulas consisting of;
space="preserve" listing-type="equation">[--Y--R.sub.17 --].sub.T, I
space="preserve" listing-type="equation">[--O--R.sub.5 --C(O)--].sub.B, III
space="preserve" listing-type="equation">([--O--R.sub.9 --(O)].sub.P --O--).sub.L G XIand combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided that X and Y cannot both be --O--;
R, R1 and R2 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R3 is selected from the group consisting of an alkylene unit and an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from 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 in the range of from 2 to 12;
R17 is an alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal --N(R18)-- or an internal --C(O)--N(R21)--;
T is an integer in the range of from 1 to 2,000;
R18 and R21 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R5 and R9 are selected from the group consisting of --C(R6)(R7)--, --(CH2)3 --O--, --CH2 --CH2 --O--CH2 --, --CR8 H--CH2 --, --(CH2)5 --, --(CH2)P -- O--C(O)-- and --(CH2)K --C(O)--CH2 --;
R6 and R7 are independently selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms;
R8 is selected from the group consisting of hydrogen and methyl;
F and K are independently selected 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.
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Abstract
The present invention describes an aliphatic polyoxaamide polymer and blends thereof that may be used to produce surgical devices such as sutures, sutures with attached needles, molded devices, and the like. The aliphatic polyoxaamide of the present invention have a first divalent repeating unit of formula I:
[X--C(O)--C(R.sub.1) (R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)
(R2)--C(O)--] I
and a second repeating unit selected from the group of formulas consisting of:
[--Y--R.sub.17 --].sub.T, I
[--O--R.sub.5 --C(O)--].sub.B, and III
([--O--R.sub.9 --C(O)].sub.P --O--) XI
and combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided both X and Y are not both --O-- and may be blended with a second polymer that is preferably biocompatable.
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Citations
26 Claims
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1. A polymer blend comprising an aliphatic polyoxaamide composed of a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[X--C(O)--C(R.sub.1) (R.sub.2)--O--(R.sub.e)--O--C(R.sub.1) (R.sub.2)--C(O)--] Iand a second repeating unit selected from the group of formulas consisting of;
space="preserve" listing-type="equation">[--Y--R.sub.17 --].sub.T, I
space="preserve" listing-type="equation">[--O--R.sub.5 --C(O)--].sub.B, III
space="preserve" listing-type="equation">([--O--R.sub.9 --(O)].sub.P --O--).sub.L G XIand combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided that X and Y cannot both be --O--;
R, R1 and R2 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R3 is selected from the group consisting of an alkylene unit and an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from 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 in the range of from 2 to 12;
R17 is an alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal --N(R18)-- or an internal --C(O)--N(R21)--;
T is an integer in the range of from 1 to 2,000;
R18 and R21 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R5 and R9 are selected from the group consisting of --C(R6)(R7)--, --(CH2)3 --O--, --CH2 --CH2 --O--CH2 --, --CR8 H--CH2 --, --(CH2)5 --, --(CH2)P -- O--C(O)-- and --(CH2)K --C(O)--CH2 --;
R6 and R7 are independently selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms;
R8 is selected from the group consisting of hydrogen and methyl;
F and K are independently selected 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; anda 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. - View Dependent Claims (2, 3, 4, 23)
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5. A device made from a polymer blend comprising an aliphatic polyoxaamides composed of a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[X--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand a second repeating unit selected from the group of formulas consisting of;
space="preserve" listing-type="equation">[--Y--R.sub.17 --].sub.T, I
space="preserve" listing-type="equation">[--O--R.sub.5 --C(O)--].sub.B, II
space="preserve" listing-type="equation">([--O--R.sub.9 --C(O)].sub.P --O--].sub.L G XIand combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided that X and Y cannot both be --O--;
R, R1 and R2 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R3 is selected from the group consisting of an alkylene unit and an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from 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 in the range of from 2 to 12;
R17 is an alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal --N(R18)-- or an internal --C(O)--N(R21)--;
T is an integer in the range of from 1 to 2,000;
R18 and R21 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R5 and R9 are selected from the group consisting of --C(R6)(R7)--, --(CH2)3 --O--, --CH2 --CH2 --O--CH2 --, --CR8 H--CH2 --, --(CH2)5 --, --(CH2)F --O--C(O)-- and --(CH2)K --C(O)--CH2 --;
R6 and R6 are independently selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms;
R8 is selected from the group consisting of hydrogen and methyl;
F and K are independently selected 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; anda 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. - View Dependent Claims (6, 7, 8, 9, 14, 15, 16, 24)
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24. The device of claim 5 wherein the aliphatic polyoxaamide contains as a second repeat unit a lactone derived repeating unit derived from lactone monomers selected from the group consisting of glycolide, d-lactide, 1-lactide, meso-lactide, ε
- -caprolactone, p-dioxanone, trimethylene carbonate, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one and combinations thereof.
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10. A device coated with a polymer blend comprising a blend of an aliphatic polyoxaamides having a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[X--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand a second repeating unit selected from the group of formulas consisting of;
space="preserve" listing-type="equation">[--Y--R.sub.17 --].sub.T, I
space="preserve" listing-type="equation">[--O--R.sub.5 --C(O)--].sub.B, III
space="preserve" listing-type="equation">([--O--R.sub.9 --C(O)].sub.P --O--).sub.L G XIand combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided that X and Y cannot both be --O--;
R, R1 and R2 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R3 is selected from the group consisting of an alkylene unit and an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[ICH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from 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 in the range of from 2 to 12;
R17 is an alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal --N(R18)-- or an internal --C(O)--N(R21)--;
T is an integer in the range of from 1 to 2,000;
R18 and R21 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R5 and R9 are selected from the group consisting of --C(R6)(R7)--, --(CH2)3 --O--, --CH2 --CH2 --O--CH2 --, --CR8 H--CH2 --, --(CH2)5 --, --(CH2)F --O--C(O)-- and --(CH2)K --C(O)--CH2 --;
R6 and R7 are independently selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms;
R8 is selected from the group consisting of hydrogen and methyl;
F and K are independently selected 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; anda 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 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°
C. - View Dependent Claims (11, 12, 17, 18, 19, 25)
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13. A drug delivery matrix comprising a drug and a polymer blend of an aliphatic polyoxaamide having a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[X--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand a second repeating unit selected from the group of formulas consisting of;
space="preserve" listing-type="equation">[--Y--R.sub.17 --].sub.T, I
space="preserve" listing-type="equation">[--O--R.sub.5 --C(O)--].sub.B, III
space="preserve" listing-type="equation">([--O--R.sub.9 --C(O)].sub.P --O--) .sub.L G XIand combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided that X and Y cannot both be --O--;
R, R1 and R2 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R3 is selected from the group consisting of an alkylene unit and an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from 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 in the range of from 2 to 12;
R17 is an alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal --N(R21)-- or an internal --C(O)--N(R21)--;
T is an integer in the range of from 1 to 2,000;
R18 and R21 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R5 and R9 are selected from the group consisting of --C(R6)(R7)--, --(CH2)3 --O--, --CH2 --CH2 --O--CH2 --, --CR8 H--CH2 --, --(CH2)5 --, --(CH2)F --O--C(O)-- and --(CH2)K --C(O)--CH2 --;
R6 and R7 are independently selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms;
R8 is selected from the group consisting of hydrogen and methyl;
F and K are independently selected 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 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; anda 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. - View Dependent Claims (20, 21, 22, 26)
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Specification