CA2373541A1 - Surface treatment of medical devices with reactive hydrophilic polymers - Google Patents
Surface treatment of medical devices with reactive hydrophilic polymers Download PDFInfo
- Publication number
- CA2373541A1 CA2373541A1 CA 2373541 CA2373541A CA2373541A1 CA 2373541 A1 CA2373541 A1 CA 2373541A1 CA 2373541 CA2373541 CA 2373541 CA 2373541 A CA2373541 A CA 2373541A CA 2373541 A1 CA2373541 A1 CA 2373541A1
- Authority
- CA
- Canada
- Prior art keywords
- hydrophilic
- reactive
- medical device
- polymer
- monomers
- Prior art date
- 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.)
- Abandoned
Links
- 229920001477 hydrophilic polymer Polymers 0.000 title claims abstract description 29
- 238000004381 surface treatment Methods 0.000 title abstract description 18
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 67
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000000576 coating method Methods 0.000 claims abstract description 24
- 239000011248 coating agent Substances 0.000 claims abstract description 23
- 230000000295 complement effect Effects 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims description 103
- 229920013730 reactive polymer Polymers 0.000 claims description 82
- -1 poly(alkyleneoxy) Polymers 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 50
- 229920000642 polymer Polymers 0.000 claims description 47
- 239000000463 material Substances 0.000 claims description 37
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 239000000017 hydrogel Substances 0.000 claims description 25
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical group O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 claims description 23
- 239000004593 Epoxy Chemical group 0.000 claims description 14
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- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 7
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- 125000003118 aryl group Chemical group 0.000 claims description 6
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- 125000006413 ring segment Chemical group 0.000 claims description 6
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- MUWZQYSJSCDUDT-UHFFFAOYSA-N 4,4-dimethyl-2-prop-1-en-2-yl-1,3-oxazol-5-one Chemical compound CC(=C)C1=NC(C)(C)C(=O)O1 MUWZQYSJSCDUDT-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002947 alkylene group Chemical group 0.000 claims 1
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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- 239000000523 sample Substances 0.000 description 8
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- 239000003999 initiator Substances 0.000 description 7
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- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000003754 machining Methods 0.000 description 6
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- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- JGHZJRVDZXSNKQ-UHFFFAOYSA-N octanoic acid methyl ester Natural products CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical class CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
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- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920002454 poly(glycidyl methacrylate) polymer Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
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- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
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- 238000010526 radical polymerization reaction Methods 0.000 description 1
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- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
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- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
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- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
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- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
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- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/28—Materials for coating prostheses
- A61L27/34—Macromolecular materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/056—Forming hydrophilic coatings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/315,620 | 1999-05-20 | ||
| US09/315,620 US6440571B1 (en) | 1999-05-20 | 1999-05-20 | Surface treatment of silicone medical devices with reactive hydrophilic polymers |
| PCT/US2000/013229 WO2000072052A1 (en) | 1999-05-20 | 2000-05-12 | Surface treatment of medical devices with reactive hydrophilic polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2373541A1 true CA2373541A1 (en) | 2000-11-30 |
Family
ID=23225286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2373541 Abandoned CA2373541A1 (en) | 1999-05-20 | 2000-05-12 | Surface treatment of medical devices with reactive hydrophilic polymers |
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1999
- 1999-05-20 US US09/315,620 patent/US6440571B1/en not_active Expired - Fee Related
-
2000
- 2000-05-12 EP EP20000928986 patent/EP1179190B1/en not_active Expired - Lifetime
- 2000-05-12 JP JP2000620386A patent/JP4544753B2/ja not_active Expired - Fee Related
- 2000-05-12 DE DE2000627289 patent/DE60027289T2/de not_active Expired - Fee Related
- 2000-05-12 AU AU47138/00A patent/AU762372B2/en not_active Ceased
- 2000-05-12 ES ES00928986T patent/ES2264665T3/es not_active Expired - Lifetime
- 2000-05-12 CN CNB008078157A patent/CN1156713C/zh not_active Expired - Fee Related
- 2000-05-12 BR BR0011610A patent/BR0011610A/pt not_active IP Right Cessation
- 2000-05-12 KR KR1020017014799A patent/KR20020013890A/ko not_active Application Discontinuation
- 2000-05-12 CA CA 2373541 patent/CA2373541A1/en not_active Abandoned
- 2000-05-12 WO PCT/US2000/013229 patent/WO2000072052A1/en not_active Application Discontinuation
- 2000-05-12 MX MXPA01011853A patent/MXPA01011853A/es not_active Application Discontinuation
- 2000-05-19 TW TW89109680A patent/TW589465B/zh not_active IP Right Cessation
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2001
- 2001-11-08 US US10/005,560 patent/US20020120084A1/en not_active Abandoned
- 2001-11-19 ZA ZA200109528A patent/ZA200109528B/en unknown
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2002
- 2002-07-17 HK HK02105310.0A patent/HK1045375B/zh not_active IP Right Cessation
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| US6440571B1 (en) | 2002-08-27 |
| DE60027289T2 (de) | 2006-08-31 |
| HK1045375B (zh) | 2006-11-24 |
| ZA200109528B (en) | 2003-02-19 |
| HK1045375A1 (en) | 2002-11-22 |
| CN1156713C (zh) | 2004-07-07 |
| US20020120084A1 (en) | 2002-08-29 |
| ES2264665T3 (es) | 2007-01-16 |
| WO2000072052A1 (en) | 2000-11-30 |
| TW589465B (en) | 2004-06-01 |
| KR20020013890A (ko) | 2002-02-21 |
| JP2003500686A (ja) | 2003-01-07 |
| CN1376270A (zh) | 2002-10-23 |
| EP1179190B1 (en) | 2006-04-12 |
| JP4544753B2 (ja) | 2010-09-15 |
| MXPA01011853A (es) | 2002-05-06 |
| AU4713800A (en) | 2000-12-12 |
| EP1179190A1 (en) | 2002-02-13 |
| DE60027289D1 (de) | 2006-05-24 |
| AU762372B2 (en) | 2003-06-26 |
| BR0011610A (pt) | 2002-07-23 |
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