CA1337004C - Composition de recouvrement resorbable, sutures ainsi recouvertes et mode de preparation - Google Patents

Composition de recouvrement resorbable, sutures ainsi recouvertes et mode de preparation

Info

Publication number: CA1337004C
Authority: CA; Canada
Prior art keywords: glycolide; lactide; suture; polyalkylene glycol; monomer
Prior art date: 1987-08-26
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

CA 575699

Other languages

English (en)

Inventor

Donald S. Kaplan

Ross R. Muth

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.)

1987-08-26

Filing date

1988-08-26

Publication date

1995-09-12

1988-08-26 Application filed by United States Surgical Corp filed Critical United States Surgical Corp

1995-09-12 Application granted granted Critical

1995-09-12 Publication of CA1337004C publication Critical patent/CA1337004C/fr

2012-09-12 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000008199 coating composition Substances 0.000 title claims abstract description 42
238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title description 5
RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims abstract description 102
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims abstract description 68
229920001577 copolymer Polymers 0.000 claims abstract description 63
239000011248 coating agent Substances 0.000 claims abstract description 48
238000000576 coating method Methods 0.000 claims abstract description 48
239000000178 monomer Substances 0.000 claims abstract description 39
229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 27
238000007334 copolymerization reaction Methods 0.000 claims abstract description 20
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 56
235000011187 glycerol Nutrition 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 19
239000002202 Polyethylene glycol Substances 0.000 claims description 15
229920001223 polyethylene glycol Polymers 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 4
229920001519 homopolymer Polymers 0.000 claims description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
238000003860 storage Methods 0.000 description 21
239000003381 stabilizer Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 16
239000003054 catalyst Substances 0.000 description 14
229920000642 polymer Polymers 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 12
238000009736 wetting Methods 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
-1 crotonic Chemical class 0.000 description 10
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 6
229910021626 Tin(II) chloride Inorganic materials 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
238000010926 purge Methods 0.000 description 6
238000002791 soaking Methods 0.000 description 6
239000001119 stannous chloride Substances 0.000 description 6
235000011150 stannous chloride Nutrition 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
230000000087 stabilizing effect Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
102000008186 Collagen Human genes 0.000 description 2
108010035532 Collagen Proteins 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
239000004348 Glyceryl diacetate Substances 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
229920000954 Polyglycolide Polymers 0.000 description 2
229920001400 block copolymer Polymers 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
229920001436 collagen Polymers 0.000 description 2
238000010276 construction Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
235000019443 glyceryl diacetate Nutrition 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
229920000747 poly(lactic acid) Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
239000003356 suture material Substances 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
KYXHKHDZJSDWEF-LHLOQNFPSA-N CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 Chemical compound CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 KYXHKHDZJSDWEF-LHLOQNFPSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
229940124326 anaesthetic agent Drugs 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000002729 catgut Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000000151 deposition Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
230000001050 lubricating effect Effects 0.000 description 1
125000005395 methacrylic acid group Chemical class 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229920001206 natural gum Polymers 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920001308 poly(aminoacid) Polymers 0.000 description 1
229920002463 poly(p-dioxanone) polymer Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000001589 sorbitan tristearate Substances 0.000 description 1
235000011078 sorbitan tristearate Nutrition 0.000 description 1
229960004129 sorbitan tristearate Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
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 1
150000003626 triacylglycerols Chemical class 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1

Landscapes

Materials For Medical Uses (AREA)

CA 575699 1987-08-26 1988-08-26 Composition de recouvrement resorbable, sutures ainsi recouvertes et mode de preparation Expired - Lifetime CA1337004C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8973487A	1987-08-26	1987-08-26
US089,734		1987-08-26

Publications (1)

Publication Number	Publication Date
CA1337004C true CA1337004C (fr)	1995-09-12

Family

ID=22219333

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 575699 Expired - Lifetime CA1337004C (fr)	1987-08-26	1988-08-26	Composition de recouvrement resorbable, sutures ainsi recouvertes et mode de preparation

Country Status (1)

Country	Link
CA (1)	CA1337004C (fr)

1988
- 1988-08-26 CA CA 575699 patent/CA1337004C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2012-09-12	MKEX	Expiry

Publication	Publication Date	Title
US5123912A (en)	1992-06-23	Absorbable coating composition, coated sutures and method of preparation
US4027676A (en)	1977-06-07	Coated sutures
US4201216A (en)	1980-05-06	Absorbable coating composition for sutures
EP0170966B1 (fr)	1992-11-11	Revêtement à sec de filaments chirurgicaux
JP4216498B2 (ja)	2009-01-28	外科用の縫合材料、その製品のための工程、およびそれの使用
US4994074A (en)	1991-02-19	Copolymers of ε-caprolactone, glycolide and glycolic acid for suture coatings
US4185637A (en)	1980-01-29	Coating composition for sutures
US4983180A (en)	1991-01-08	Coated sutures exhibiting improved knot security
JPS6127057B2 (fr)	1986-06-24
CA1297226C (fr)	1992-03-10	Enduit pour sutures chirurgicales
US5032638A (en)	1991-07-16	Bioabsorbable coating for a surgical device
US5051272A (en)	1991-09-24	Method for improving the storage stability of a polymeric article susceptible to hydrolytic degradation and resulting article
US4047533A (en)	1977-09-13	Absorbable surgical sutures coated with polyoxyethylene-polyoxypropylene copolymer lubricant
AU633681B2 (en)	1993-02-04	Suture coated with polyvinyl ester
EP0214861A1 (fr)	1987-03-18	Sutures chirurgicales
CA2055420A1 (fr)	1992-05-15	Suture enduite d'un polyetheramide
AU600753B2 (en)	1990-08-23	Surgical filament coating
EP1581121A2 (fr)	2005-10-05	Sutures enduites d'huile
EP0839540B1 (fr)	2004-03-31	Fil de suture en boyau revêtu
JP4215845B2 (ja)	2009-01-28	手術用品のためのコーテイング混合物
CA1100370A (fr)	1981-05-05	Compose d'enrobage absorbable pour fils de suture
CA1337004C (fr)	1995-09-12	Composition de recouvrement resorbable, sutures ainsi recouvertes et mode de preparation
US5939191A (en)	1999-08-17	Coated gut suture
EP0774265A1 (fr)	1997-05-21	Fil de suture en boyau revêtu
KR0157510B1 (ko)	1999-02-01	봉합사용 흡수성 코팅 조성물 및 이로 코팅된 수술용 봉합사