# US 8,784,861 B2 · Swellable fiber- and microfiber-forming polyether-esters and applications thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,784,861 B2 - Document ID: US8784861B2 - Status: Granted - Kind: B2 - Application number: 11/820,849 - Filed: 2007-06-20 - Published: 2007-11-29 - Granted: 2014-07-22 - Earliest claimed: 2005-06-15 - Assignees: Poly-Med, Inc. - Applicants: Shalaby W. Shalaby; James M. Lindsey - Inventors: Shalaby W. Shalaby; James M. Lindsey - Web page: https://patentgrep.com/patent/US8784861B2 ## CPC - A61L 17/105: {Polyesters not covered by A61L17/12} - A61L 17/005: {containing a biologically active substance, e.g. a medicament or a biocide} - A61L 17/145: {Coating} - A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds - A61L 27/34: Macromolecular materials - A61L 27/54: Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)} - A61L 27/58: Materials at least partially resorbable by the body - A61L 29/085: {Macromolecular materials} - A61L 31/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds {(A61L31/041 takes precedence)} - A61L 31/10: Macromolecular materials - A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)} - C08G 63/664: derived from hydroxy carboxylic acids - C08G 63/668: derived from polycarboxylic acids and polyhydroxy compounds - C08G 64/183: {containing polyether sequences} - C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence) - A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents - A61L 2300/412: Tissue-regenerating or healing or proliferative agents - A61L 2300/416: Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus - Y10T 442/60: Nonwoven fabric [i.e., nonwoven strand or fiber material] - 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 (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract Biomedical and tissue engineering devices, such as surgical sutures and microporous scaffolds, respectively, which undergo swelling and increase in dimensions when placed in aqueous environments such as living tissues, are produced by the melt-spinning or electrostatic spinning into strong monofilament and multifilament yarns or microfibrous fabrics, respectively. Such devices are formed from especially high molecular weight crystalline polyether-esters having a minimum inherent viscosity of 0.8 dL/g and heat of fusion of at least 5 J/g, wherein the polyether-esters are made by grafting to a polyester component a polyether glycol component having a minimum molecular weight of about 1 kDa with at least one cyclic monomer. ## Claims ### Claim 1 A swellable, absorbable, fiber- or microfiber-forming, high molecular weight, crystalline polyether-ester having a polyether chain component with a molecular weight of more than about 11 kDa; an inherent viscosity of at least 0.8 dL/g in chloroform or hexafluoroisopropyl alcohol; heat of fusion of greater than 5 J/g, and wherein the ratio of the polyester monomers to catalyst used to prepare the polyether-ester is from 3000 to 16000, and wherein fibers or microfibers formed therefrom undergo at least 0.5% increase in their cross-sectional area when placed in an aqueous environment for less than three (3) hours. ### Claim 2 (depends on 1) A swellable, absorbable, high molecular weight, crystalline polyether-ester as in claim 1 comprising a polyether glycol grafted with at least one cyclic monomer selected from the group consisting of l-lactide, ε-caprolactone, glycolide, p-dioxanone, trimethylene carbonate, and a morpholinedione. ### Claim 3 (depends on 2) A swellable, absorbable, high molecular weight, crystalline polyether-ester as in claim 2 wherein the polyether chain component is a polyethylene oxide. ### Claim 4 (depends on 2) A swellable, absorbable, high molecular weight, crystalline polyether-ester as in claim 2 wherein the polyether chain component is a block copolymer of polyethylene oxide and polypropylene oxide. ### Claim 5 (depends on 2) A swellable, absorbable, high molecular weight, crystalline polyether-ester as in claim 2 wherein the polyether chain component is a random copolymer of ethylene oxide and propylene oxide. ### Claim 6 (depends on 2) A melt-spun monofilament yarn for use as a surgical suture formed from the swellable, absorbable, high molecular weight, crystalline polyether-ester as in claim 2. ### Claim 7 (depends on 2) A melt-spun multifilament yarn for use as a surgical suture formed from the swellable, absorbable, high molecular weight, crystalline polyether-ester as in claim 2. ### Claim 8 (depends on 2) A multifilament yarn formed into a compressible, microporous felt for use as a scaffold for tissue engineering formed from the swellable, absorbable, high molecular weight, crystalline polyether-ester as in claim 2. ### Claim 9 (depends on 2) A non-woven, microporous, microfibrous fabric made by electrostatic spinning of a solution the swellable, absorbable, high molecular weight, crystalline polyether-ester as in claim 2. ### Claim 10 (depends on 6) The melt-spun monofilament yarn for use as a surgical suture set forth in claim 6 having a breaking strength of more than 30 kpsi and a modulus of less than 300 kpsi. ### Claim 11 (depends on 10) The melt-spun monofilament yarn for use as a surgical suture set forth in claim 10 wherein the suture modulus decreases by at least 5% after less than 3 hours following its placement in an aqueous environment as in living tissues. ### Claim 12 (depends on 6) The melt-spun monofilament yarn for use as a surgical suture set forth in claim 6 in the form of a monofilament suture having an absorbable coating, the coating containing at least one bioactive agent selected from antimicrobial agents, antineoplastic agents, and tissue growth promoting agents. ### Claim 13 (depends on 7) The melt-spun monofilament yarn for use as a surgical suture set forth in claim 7 in the form of a multifilament suture having an absorbable coating, the coating containing at least one bioactive agent selected from antimicrobial agents, antineoplastic agents, and tissue growth promoting agents. ### Claim 14 (depends on 8) A multifilament yarn formed into a compressible, microporous felt for use as a scaffold for tissue engineering as set forth in claim 8 wherein the compressible felt comprises an absorbable coating, the coating containing at least one bioactive agent selected from antimicrobial agents, antineoplastic agents, and tissue growth promoting agents. ### Claim 15 (depends on 6) A melt-spun monofilament yarn for use as a surgical suture as set forth in claim 6 wherein the monofilament suture comprises at least one bioactive agent selected from antimicrobial agents, antineoplastic agents and tissue growth promoting agents. ### Claim 16 (depends on 6) A melt-spun monofilament yarn for use as a surgical suture as set forth in claim 6 wherein the monofilament suture, upon implanting in living tissues, exhibits a ratio of the percent breaking strength retention/absorption at a designated time period that is at least 5% lower than that of a corresponding polyester lacking the polyether chain component. ### Claim 17 A swellable, absorbable, fiber- or microfiber-forming, high molecular weight, crystalline polyether-ester comprising: a polyether chain component with a molecular weight of more than about 11 kDa; an inherent viscosity of at least 0.8 dL/g in chloroform or hexafluoroisopropyl alcohol; a heat of fusion of greater than 5 J/g; wherein fibers or microfibers formed therefrom undergo at least 0.5% increase in their cross-sectional area when placed in an aqueous environment for less than three (3) hours; and wherein the polyether-ester comprises a pentablock polymer having a central polyether glycol block interlinked with cyclic monomers and having polyester end blocks. ### Claim 18 (depends on 17) The swellable, absorbable, fiber- or microfiber-forming, high molecular weight, crystalline polyether-ester of claim 17, wherein the cyclic monomers comprise trimethylene carbonate or ε-caprolactone. ### Claim 19 A swellable, absorbable, fiber- or microfiber-forming, high molecular weight, crystalline polyether-ester comprising: a polyether chain component with a molecular weight of more than about 11 kDa; an inherent viscosity of at least 0.8 dL/g in chloroform or hexafluoroisopropyl alcohol; a heat of fusion of greater than 5 J/g; wherein fibers or microfibers formed therefrom undergo at least 0.5% increase in their cross-sectional area when placed in an aqueous environment for less than three (3) hours; and wherein the polyether-ester comprises a triblock copolymer having a central polyether glycol block and each end block having less than 20% by mole of a cyclic monomer selected from the group consisting of l-lactide, ε-caprolactone, p-dioxanone, trimethylene carbonate, morpholinedione or mixtures thereof. ### Claim 20 (depends on 19) The swellable, absorbable, fiber- or microfiber-forming, high molecular weight, crystalline polyether-ester of claim 19, and each end block further comprising greater than 80% by mole glycolide.