JP2005512115A - 生医学的物品の表面を修飾する方法 - Google Patents
生医学的物品の表面を修飾する方法 Download PDFInfo
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- JP2005512115A JP2005512115A JP2003544501A JP2003544501A JP2005512115A JP 2005512115 A JP2005512115 A JP 2005512115A JP 2003544501 A JP2003544501 A JP 2003544501A JP 2003544501 A JP2003544501 A JP 2003544501A JP 2005512115 A JP2005512115 A JP 2005512115A
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- Prior art keywords
- radical
- alkyl
- formula
- alkylene
- substituted
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 37
- 239000000463 material Substances 0.000 claims abstract description 64
- 229920000831 ionic polymer Polymers 0.000 claims abstract description 44
- 239000013590 bulk material Substances 0.000 claims abstract description 29
- 238000000576 coating method Methods 0.000 claims abstract description 19
- 239000011248 coating agent Substances 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 9
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- -1 benzylene Chemical group 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 239000003999 initiator Substances 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 229920002125 Sokalan® Polymers 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000004584 polyacrylic acid Substances 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229920000083 poly(allylamine) Polymers 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229920002674 hyaluronan Polymers 0.000 claims description 9
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- 125000001424 substituent group Chemical group 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
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- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000010526 radical polymerization reaction Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
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- 210000004087 cornea Anatomy 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- 108010038807 Oligopeptides Proteins 0.000 claims description 3
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- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 3
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 229960002591 hydroxyproline Drugs 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims description 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims 4
- RBIIKVXVYVANCQ-CUWPLCDZSA-N (2s,4s,5s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-6-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-4-hydroxy-2-propan-2-ylhexanamide Chemical group C1C(C)(C)N(C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)CC(=O)N1C1=CC=CC=C1Cl RBIIKVXVYVANCQ-CUWPLCDZSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 125000004964 sulfoalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000758 substrate Substances 0.000 abstract description 6
- 230000035699 permeability Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 121
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 40
- 229920000642 polymer Polymers 0.000 description 25
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 229910052786 argon Inorganic materials 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 14
- 229920006317 cationic polymer Polymers 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 13
- 238000004448 titration Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000000129 anionic group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
- 238000004483 ATR-FTIR spectroscopy Methods 0.000 description 5
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- IIQWTZQWBGDRQG-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C(C)=C IIQWTZQWBGDRQG-UHFFFAOYSA-N 0.000 description 5
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- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
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- A—HUMAN NECESSITIES
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- 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
-
- 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
-
- 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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- General Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Medical Uses (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Eyeglasses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01811088 | 2001-11-13 | ||
| PCT/EP2002/012658 WO2003042724A1 (en) | 2001-11-13 | 2002-11-12 | Method for modifying the surface of biomedical articles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005512115A true JP2005512115A (ja) | 2005-04-28 |
| JP2005512115A5 JP2005512115A5 (enExample) | 2006-01-12 |
Family
ID=8184238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003544501A Pending JP2005512115A (ja) | 2001-11-13 | 2002-11-12 | 生医学的物品の表面を修飾する方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6878399B2 (enExample) |
| EP (1) | EP1451615B1 (enExample) |
| JP (1) | JP2005512115A (enExample) |
| AT (1) | ATE378612T1 (enExample) |
| CA (1) | CA2467092A1 (enExample) |
| DE (1) | DE60223589T2 (enExample) |
| TW (1) | TW200407367A (enExample) |
| WO (1) | WO2003042724A1 (enExample) |
Cited By (1)
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| JP2009227809A (ja) * | 2008-03-21 | 2009-10-08 | Fujifilm Corp | 親水性組成物及び親水性処理部材 |
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| JP7564197B2 (ja) | 2019-11-04 | 2024-10-08 | アルコン インク． | 異なる柔軟性を有する表面を有するコンタクトレンズ |
| EP4369081B1 (en) | 2019-12-16 | 2025-06-25 | Alcon Inc. | Method for producing an ophthalmic product |
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| WO2024220971A1 (en) * | 2023-04-21 | 2024-10-24 | Azul 3D, Inc. | Optical lenses, optical components, and methods of manufacturing optical components |
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2002
- 2002-11-11 TW TW091133009A patent/TW200407367A/zh unknown
- 2002-11-12 AT AT02779553T patent/ATE378612T1/de not_active IP Right Cessation
- 2002-11-12 JP JP2003544501A patent/JP2005512115A/ja active Pending
- 2002-11-12 WO PCT/EP2002/012658 patent/WO2003042724A1/en not_active Ceased
- 2002-11-12 EP EP02779553A patent/EP1451615B1/en not_active Expired - Lifetime
- 2002-11-12 US US10/292,836 patent/US6878399B2/en not_active Expired - Fee Related
- 2002-11-12 CA CA002467092A patent/CA2467092A1/en not_active Abandoned
- 2002-11-12 DE DE60223589T patent/DE60223589T2/de not_active Expired - Lifetime
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| WO1999035520A1 (en) * | 1998-01-09 | 1999-07-15 | Novartis Ag | Coating of polymers |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007252699A (ja) * | 2006-03-24 | 2007-10-04 | Mcrotech Kk | ゲル組成物、それを用いた移植用材料及びそれらの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1451615B1 (en) | 2007-11-14 |
| ATE378612T1 (de) | 2007-11-15 |
| TW200407367A (en) | 2004-05-16 |
| US20030219533A1 (en) | 2003-11-27 |
| CA2467092A1 (en) | 2003-05-22 |
| WO2003042724A1 (en) | 2003-05-22 |
| DE60223589T2 (de) | 2008-11-20 |
| EP1451615A1 (en) | 2004-09-01 |
| US6878399B2 (en) | 2005-04-12 |
| DE60223589D1 (de) | 2007-12-27 |
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