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US 5,644,002 AGranted
Absorbable polyalkylene diglycolates
AssigneeEthicon, Inc.
InventorsKevin Cooper, Angelo Scopelianos
Life of this patent
Estimating the term…
Abstract
Absorbable polymers and blends of poly(alkylene diglycolate)s and aliphatic polyesters based on lactone monomers such as lactide, glycolide, e-caprolactone, p-dioxanone, and trimethylene carbonate are described. The polymers and blends exhibit a broad range of properties, useful in a variety of medical devices.
Claims23
An absorbable, block, segmented, statistically random, or graft copolymer comprising the reaction product of:
- a) an absorbable, biocompatible poly(alkylene diglycolate), comprising the reaction product of::
- an acid or ester of diglycolic acid;
- and,
- an alcohol selected from the group consisting of glycerol, pentaerythitol, trimethylolpropane, hydroxyl terminated poly(ethylene glycol)s, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butylene glycol, dipropylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, and 1,8-octanediol,
- wherein the poly(alkylene diglycolate) comprises about 10 mole percent to about 90 mole percent of repeating units with tri-, tetra-alcohols, and hydroxyl terminated poly(ethylene glycol)s, and wherein the balance of the poly(alkylene diglycolate) comprises repeating units with diol alcohols, and,
- b) a polyester formed from lactone monomers selected from the group consisting of p-dioxanone, e-caprolactone, delta-valerolactone, beta-butyrolactone, epsilon-decalactone, 2,5-diketomorpholine, pivalolactone, alpha, alpha-diethylpropiolactone, ethylene oxalate, 3-methyl-1,4-dioxane-2,5-dione, 3,3-diethyl-1,4-dioxan-2,5-dione, gamma-butyrolactone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one, 1,4-dioxan-2-one, 6,8-dioxabicycloctane-7-one, and combinations of two and more thereof,
- wherein the copolymer is comprised of about 10 weight percent to about 90 weight percent of poly(alkylene diglycolate).
4 more elements
An absorbable polymer blend, comprising:
- a) an absorbable, biocompatible poly(alkylene diglycolate) comprising the reaction product of:
- an acid or ester of diglycolic acid;
- and,
- an alcohol selected from the group consisting of glycerol, pentaerythitol, trimethylolpropane, hydroxyl terminated poly(ethylene glycol)s, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butylene glycol, dipropylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, and 1,8-octanediol,
- wherein the poly(alkylene diglycolate) comprises about 10 mole percent to about 90 mole percent of repeating units with tri-, tetra-alcohols, and hydroxyl terminated poly(ethylene glycol)s, and wherein the balance of the poly(alkylene diglycolate) comprises repeating units with diol alcohols, and,
- b) a polyester formed from lactone monomers selected from the group consisting of p-dioxanone, e-caprolactone, delta-valerolactone, beta-butyrolactone, epsilon-decalactone, 2,5-diketomorpholine, pivalolactone, alpha, alpha-diethylpropiolactone, ethylene oxalate, 3-methyl-1,4-dioxane-2,5-dione, 3,3-diethyl-1,4-dioxan-2,5-dione, gamma-butyrolactone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one, 1,4-dioxan-2-one, 6,8-dioxabicycloctane-7-one, and combinations of two and more thereof,
- wherein the blend is comprised of about 10 weight percent to about 90 weight percent of poly(alkylene diglycolate).
4 more elements
An absorbable device for use in medical applications, the medical device comprising a block, segmented, statistically random, or graft copolymer comprising the reaction product of:
- a) an absorbable, biocompatible poly(alkylene diglycolate) comprising the reaction product of:
- an acid or ester of diglycolic acid;
- and,
- an alcohol selected from the group consisting of glycerol, pentaerythitol, trimethylolpropane, hydroxyl terminated poly(ethylene glycol)s, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butylene glycol, dipropylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, and 1,8-octanediol,
- wherein the poly(alkylene diglycolate) comprises about 10 mole percent to about 90 mole percent of repeating units with tri-, tetra-alcohols, and hydroxyl terminated poly(ethylene glycol)s, and wherein the balance of the poly(alkylene diglycolate) comprises repeating units with diol alcohols, and,
- b) a polyester formed from lactone monomers selected from the group consisting of p-dioxanone, e-caprolactone, delta-valerolactone, beta-butyrolactone, epsilon-decalactone, 2,5-diketomorpholine, pivalolactone, alpha, alpha-diethylpropiolactone, ethylene oxalate, 3-methyl-1,4-dioxane-2,5-dione, 3,3-diethyl-1,4-dioxan-2,5-dione, gamma-butyrolactone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one, 1,4-dioxan-2-one, 6,8-dioxabicycloctane-7-one, and combinations of two and more thereof,
- wherein the copolymer is comprised of about 10 weight percent to about 90 weight percent of poly(alkylene diglycolate).
4 more elements
An absorbable device for use in medical applications, the medical device comprising a blend of:
- a) an absorbable biocompatible poly(alkylene diglycolate) comprising the reaction product of:
- an acid or ester of diglycolic acid;
- and,
- an alcohol selected from the group consisting of glycerol, pentaerythitol, trimethylolpropane, hydroxyl terminated poly(ethylene glycol)s, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butylene glycol, dipropylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, and 1,8-octanediol,
- wherein the poly(alkylene diglycolate) comprises about 10 mole percent to about 90 mole percent of repeating units with tri-, tetra-alcohols, and hydroxyl terminated poly(ethylene glycol)s, and wherein the balance of the poly(alkylene diglycolate) comprises repeating units with diol alcohols, and,
- b) a polyester formed from lactone monomers selected from the group consisting of p-dioxanone, e-caprolactone, delta-valerolactone, beta-butyrolactone, epsilon-decalactone, 2,5-diketomorpholine, pivalolactone, alpha, alpha-diethylpropiolactone, ethylene oxalate, 3-methyl-1,4-dioxane-2,5-dione, 3,3-diethyl-1,4-dioxan-2,5-dione, gamma-butyrolactone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one, 1,4-dioxan-2-one, 6,8-dioxabicycloctane-7-one, and combinations of two and more thereof,
- wherein the blend is comprised of about 10 weight percent to about 90 weight percent of poly(alkylene diglycolate).
4 more elements
A process for preparing a block, segmented, statistically random, or graft copolymer, comprising:
- a) polymerizing a poly(alkylene diglycolate), wherein the poly(alkylene diglycolate) comprises the reaction product of:
- an acid or ester of diglycolic acid;
- and,
- an alcohol selected from the group consisting of glycerol, pentaerythitol, trimethylolpropane, hydroxyl terminated poly(ethylene glycol)s, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butylene glycol, dipropylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, and 1,8-octanediol,
- wherein the poly(alkylene diglycolate) comprises about 10 mole percent to about 90 mole percent of repeating units with tri-, tetra-alcohols, and hydroxyl terminated poly(ethylene glycol)s, and wherein the balance of the poly(alkylene diglycolate) comprises repeating units with diol alcohols, and
- b) melt transesterifying the poly(alkylene diglycolate) with a polyester formed from lactone monomers selected from the group consisting of p-dioxanone, e-caprolactone, delta-valerolactone, beta-butyrolactone, epsilon-decalactone, 2,5-diketomorpholine, pivalolactone, alpha, alpha-diethylpropiolactone, ethylene oxalate, 3-methyl-1,4-dioxane-2,5-dione, 3,3-diethyl-1,4-dioxan-2,5-dione, gamma-butyrolactone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one, 1,4-dioxan-2-one, 6,8-dioxabicycloctane-7-one, and combinations of two and more thereof,
- wherein the copolymer is comprised of about 10 weight percent to about 90 weight percent of poly(alkylene diglycolate).
4 more elements
A process for preparing a blend comprising:
- mixing a poly(alkylene diglycolate) comprising the reaction product of:
- an acid or ester of diglycolic acid;
- and,
- an alcohol selected from the group consisting of glycerol, pentaerythitol, trimethylolpropane, hydroxyl terminated poly(ethylene glycol)s, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butylene glycol, dipropylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, and 1,8-octanediol,
- wherein the poly(alkylene diglycolate) comprises about 10 mole percent to about 90 mole percent of repeating units with tri-, tetra-alcohols, and hydroxyl terminated poly(ethylene glycol)s, and wherein the balance of the poly(alkylene diglycolate) comprises repeating units with diol alcohols, with a polyester formed from lactone monomers selected from the group consisting of p-dioxanone, e-caprolactone, delta-valerolactone, beta-butyrolactone, epsilon-decalactone, 2,5-diketomorpholine, pivalolactone, alpha, alpha-diethylpropiolactone, ethylene oxalate, 3-methyl-1,4-dioxane-2,5-dione, 3,3-diethyl-1,4-dioxan-2,5-dione, gamma-butyrolactone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one, 1,4-dioxan-2-one, 6,8-dioxabicycloctane-7-one, and combinations of two and more thereof,
- wherein the blend is comprised of about 10 weight percent to about 90 weight percent of poly(alkylene diglycolate).
3 more elements
A process for preparing a block, segmented, statistically random, or graft copolymer, comprising:
- a) polymerizing a poly(alkylene diglycolate), wherein the poly (alkylene diglycolate) comprises the reaction product of:
- an acid or ester of diglycolic acid;
- and,
- an alcohol selected from the group consisting of glycerol, pentaerythitol, trimethylolpropane, hydroxyl terminated poly(ethylene glycol)s, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butylene glycol, dipropylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, and 1,8-octanediol,
- wherein the poly(alkylene diglycolate) comprises about 10 mole percent to about 90 mole percent of repeating units with tri-, tetra-alcohols, and hydroxyl terminated poly(ethylene glycol)s, and wherein the balance of the poly(alkylene diglycolate) comprises repeating units with diol alcohols, and
- b) melt transesterifying the poly(alkylene diglycolate) with a polyester formed from lactone monomers selected from the group consisting of glycolide and lactide,
- wherein the copolymer is comprised of about 55 weight percent to about 95 weight percent of poly(alkylene diglycolate).
4 more elements
A process for preparing a blend comprising:
- mixing a poly(alkylene diglycolate) comprising the reaction product of:
- an acid or ester of diglycolic acid;
- and,
- an alcohol selected from the group consisting of glycerol, pentaerythitol, trimethylolpropane, hydroxyl terminated poly(ethylene glycol)s, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butylene glycol, dipropylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, and 1,8-octanediol,
- wherein the poly(alkylene diglycolate) comprises about 10 mole percent to about 90 mole percent of repeating units with tri-, tetra-alcohols, and hydroxyl terminated poly(ethylene glycol)s, and wherein the balance of the poly(alkylene diglycolate) comprises repeating units with diol alcohols, with a polyester formed from lactone monomers selected from the group consisting of glycolide and lactide,
- wherein the blend is comprised of about 55 weight percent to about 95 weight percent of poly(alkylene diglycolate).
3 more elements
Dependencies are inferred from the claim text.