CA2079274C - Melanges de polymeres de glycolide et de lactide et de caprolactone et de polymeres de carbonate de trimethylene, et sutures resorbables fabriquees a partir de ces materiaux - Google Patents

Melanges de polymeres de glycolide et de lactide et de caprolactone et de polymeres de carbonate de trimethylene, et sutures resorbables fabriquees a partir de ces materiaux Download PDF

Info

Publication number: CA2079274C
Authority: CA; Canada
Prior art keywords: glycolide; lactide; copolymers; homopolymer; caprolactone
Prior art date: 1991-09-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA002079274A

Other languages

English (en)

Other versions

CA2079274A1 (fr

Inventor

Donald S. Kaplan

Ross R. Muth

Matthew Hermes

John Kennedy

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

United States Surgical Corp

Original Assignee

United States Surgical Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-09-30

Filing date

1992-09-28

Publication date

2004-11-30

1992-09-28 Application filed by United States Surgical Corp filed Critical United States Surgical Corp

1993-03-31 Publication of CA2079274A1 publication Critical patent/CA2079274A1/fr

2004-11-30 Application granted granted Critical

2004-11-30 Publication of CA2079274C publication Critical patent/CA2079274C/fr

2012-09-28 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 title claims abstract description 112
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 title claims abstract description 74
239000000203 mixture Substances 0.000 title claims description 86
229920000642 polymer Polymers 0.000 title claims description 50
YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 title claims description 22
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 title claims description 20
229920001577 copolymer Polymers 0.000 claims abstract description 74
229920001519 homopolymer Polymers 0.000 claims abstract description 46
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 6
BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 4
210000000988 bone and bone Anatomy 0.000 claims description 4
229920001610 polycaprolactone Polymers 0.000 abstract description 25
239000004632 polycaprolactone Substances 0.000 abstract description 25
-1 polytrimethylene carbonate Polymers 0.000 abstract description 12
229920000166 polytrimethylene carbonate Polymers 0.000 abstract description 12
229920002959 polymer blend Polymers 0.000 abstract description 8
125000004122 cyclic group Chemical group 0.000 abstract description 6
239000000523 sample Substances 0.000 description 14
238000012360 testing method Methods 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000000178 monomer Substances 0.000 description 11
238000002347 injection Methods 0.000 description 8
239000007924 injection Substances 0.000 description 8
238000000034 method Methods 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
238000000137 annealing Methods 0.000 description 5
230000009477 glass transition Effects 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000007943 implant Substances 0.000 description 5
238000001746 injection moulding Methods 0.000 description 5
239000003054 catalyst Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000002156 mixing Methods 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
238000010926 purge Methods 0.000 description 3
JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229920002988 biodegradable polymer Polymers 0.000 description 2
239000004621 biodegradable polymer Substances 0.000 description 2
239000002131 composite material Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000013068 control sample Substances 0.000 description 2
238000009863 impact test Methods 0.000 description 2
238000002513 implantation Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
OORRCVPWRPVJEK-UHFFFAOYSA-N 2-oxidanylethanoic acid Chemical compound OCC(O)=O.OCC(O)=O OORRCVPWRPVJEK-UHFFFAOYSA-N 0.000 description 1
229920000954 Polyglycolide Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000007373 indentation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000000465 moulding Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920000747 poly(lactic acid) Polymers 0.000 description 1
239000004633 polyglycolic acid Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000003303 reheating Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
239000012780 transparent material Substances 0.000 description 1
229920000428 triblock copolymer Polymers 0.000 description 1

Landscapes

Polyesters Or Polycarbonates (AREA)
Materials For Medical Uses (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA002079274A 1991-09-30 1992-09-28 Melanges de polymeres de glycolide et de lactide et de caprolactone et de polymeres de carbonate de trimethylene, et sutures resorbables fabriquees a partir de ces materiaux Expired - Lifetime CA2079274C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US76816891A	1991-09-30	1991-09-30
US07/768,168		1991-09-30

Publications (2)

Publication Number	Publication Date
CA2079274A1 CA2079274A1 (fr)	1993-03-31
CA2079274C true CA2079274C (fr)	2004-11-30

Family

ID=25081748

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002079274A Expired - Lifetime CA2079274C (fr)	1991-09-30	1992-09-28	Melanges de polymeres de glycolide et de lactide et de caprolactone et de polymeres de carbonate de trimethylene, et sutures resorbables fabriquees a partir de ces materiaux

Country Status (1)

Country	Link
CA (1)	CA2079274C (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5641501A (en) *	1994-10-11	1997-06-24	Ethicon, Inc.	Absorbable polymer blends
EP0949299B1 (fr)	1998-04-06	2005-06-15	Ethicon, Inc.	Matrice polymérique à deux phases biocompatible, résorbable et thermoformable pour utilisation dans les articles médicaux
CN116036386B (zh) *	2023-02-22	2024-04-30	天津纳博特医疗器械有限公司	一种可吸收玻纤增强聚乳酸复合材料及颅颌面钉板系统

1992
- 1992-09-28 CA CA002079274A patent/CA2079274C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2079274A1 (fr)	1993-03-31

Legal Events

Date	Code	Title	Description
1999-08-04	EEER	Examination request
2012-09-28	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20120928

Publication	Publication Date	Title
US5475063A (en)	1995-12-12	Blends of glycolide and/or lactide polymers and caprolactone and/or trimethylene carbonate polymers and absorbable surgical devices made
US6228954B1 (en)	2001-05-08	Blends of glycolide and/or lactide polymers and caprolactone and/or trimethylene carbonate polymers and absorabable surgical devices made therefrom
EP0107591B1 (fr)	1990-01-31	Articles chirurgicaux absorbables
US4744365A (en)	1988-05-17	Two-phase compositions for absorbable surgical devices
EP0667885B1 (fr)	1997-07-16	Composition de polylactide et/ou de glycolide modifiee au caoutchouc
KR0173469B1 (ko)	1999-03-20	변형성 외과용 복구 장치
US4844854A (en)	1989-07-04	Process for making a surgical device using two-phase compositions
JP3218055B2 (ja)	2001-10-15	生吸収性セグメント化コポリマー
US4839130A (en)	1989-06-13	Process of making an absorbable surgical device
CA2459801C (fr)	2012-01-10	Copolymeres poly(l-lactide-co-glycolide), procedes de production et utilisation de ces copolymeres et dispositifs contenant ces copolymeres
US5424346A (en)	1995-06-13	Biodegradable replacement of crystal polystyrene
Cai et al.	2000	Synthesis and degradation of a tri-component copolymer derived from glycolide, L-lactide, and ε-caprolactone
US5633342A (en)	1997-05-27	Method for the synthesis of environmentally degradable block copolymers
WO1997015609A9 (fr)	1997-07-24	Procede de synthese de copolymeres sequences degradables dans l'environnement
EP0440416A2 (fr)	1991-08-07	Copolymères cristallins de la p-dioxanone et de l'epsilon-caprolactone
Grijpma et al.	1993	Poly (L-lactide) crosslinked with spiro-bis-dimethylene-carbonate
US5124103A (en)	1992-06-23	Two phase compositions for absorbable surgical devices
CA2079275A1 (fr)	1993-03-31	Melanges de polymeres de glycolide et de lactide et de homopolymeres et copolymeres poly(p-dioxanone), et sutures resorbables fabriquees a partir de ces materiaux
EP0588975B1 (fr)	1997-09-10	Copolymeres a base d'esters cycliques, et leur utilisation en tant qu'implants chirurgicaux
Bagheri et al.	2007	Synthesis and characterization of biodegradable random copolymers of L-lactide, glycolide and trimethylene carbonate
EP1311581B1 (fr)	2008-09-10	Resine polymere absorbable a haute consistance
AU2001290515A1 (en)	2002-05-23	High consistency absorbable polymeric resin
WO2006058305A2 (fr)	2006-06-01	Sutures monofilamentaires resorbables durables et flexibles
MXPA98008072A (en)	1999-06-01	Crystalline copolymers and methods to produce such copolime