TWI426932B - 眼科與耳鼻喉科裝置材料(三) - Google Patents
眼科與耳鼻喉科裝置材料(三) Download PDFInfo
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- TWI426932B TWI426932B TW097137895A TW97137895A TWI426932B TW I426932 B TWI426932 B TW I426932B TW 097137895 A TW097137895 A TW 097137895A TW 97137895 A TW97137895 A TW 97137895A TW I426932 B TWI426932 B TW I426932B
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- independently
- macromonomer
- methacrylate
- Prior art date
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- 239000000463 material Substances 0.000 title claims description 83
- 239000000178 monomer Substances 0.000 claims description 32
- 238000006116 polymerization reaction Methods 0.000 claims description 23
- -1 2-methacrylic acid 2- Benzyloxyethyl ester Chemical class 0.000 claims description 18
- 239000013078 crystal Substances 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
- 239000006096 absorbing agent Substances 0.000 claims description 6
- 239000003086 colorant Substances 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims description 4
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 claims description 4
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims description 3
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 3
- 239000007943 implant Substances 0.000 claims description 3
- WTJTUKSVRGVSNZ-UHFFFAOYSA-N 2-(2-phenoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC1=CC=CC=C1 WTJTUKSVRGVSNZ-UHFFFAOYSA-N 0.000 claims description 2
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 2
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 claims description 2
- DJENTNKTVLSRNS-UHFFFAOYSA-N 3-phenylmethoxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOCC1=CC=CC=C1 DJENTNKTVLSRNS-UHFFFAOYSA-N 0.000 claims description 2
- RXXZODOCQIRRQA-UHFFFAOYSA-N 3-phenylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC1=CC=CC=C1 RXXZODOCQIRRQA-UHFFFAOYSA-N 0.000 claims description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- IGVCHZAHFGFESB-UHFFFAOYSA-N 4-phenylbutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCC1=CC=CC=C1 IGVCHZAHFGFESB-UHFFFAOYSA-N 0.000 claims description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 2
- RXPPWNDYCIQFQB-UHFFFAOYSA-N 5-phenylpentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCC1=CC=CC=C1 RXPPWNDYCIQFQB-UHFFFAOYSA-N 0.000 claims description 2
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims description 2
- FNFHMERPSBNGRL-UHFFFAOYSA-N [4-(2-methylprop-2-enoyloxymethyl)phenyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=C(COC(=O)C(C)=C)C=C1 FNFHMERPSBNGRL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 238000009423 ventilation Methods 0.000 claims description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- QFNYOIKHNYCFRG-UHFFFAOYSA-N 2-(2-phenoxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC1=CC=CC=C1 QFNYOIKHNYCFRG-UHFFFAOYSA-N 0.000 claims 1
- PAVGMLBHCOPIEI-UHFFFAOYSA-N 2-(2-phenylmethoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCC1=CC=CC=C1 PAVGMLBHCOPIEI-UHFFFAOYSA-N 0.000 claims 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims 1
- ROJWTNWAEYEKMO-UHFFFAOYSA-N 2-phenylmethoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCC1=CC=CC=C1 ROJWTNWAEYEKMO-UHFFFAOYSA-N 0.000 claims 1
- SJOIDEGZPXSHOC-UHFFFAOYSA-N 3-phenylmethoxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOCC1=CC=CC=C1 SJOIDEGZPXSHOC-UHFFFAOYSA-N 0.000 claims 1
- PKBZUGSITIBLFK-UHFFFAOYSA-N 3-phenylpropyl prop-2-enoate Chemical compound C=CC(=O)OCCCC1=CC=CC=C1 PKBZUGSITIBLFK-UHFFFAOYSA-N 0.000 claims 1
- MXNDNUJKPFXJJX-UHFFFAOYSA-N 4-phenylbutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCC1=CC=CC=C1 MXNDNUJKPFXJJX-UHFFFAOYSA-N 0.000 claims 1
- FBOYEYXUKAKVDL-UHFFFAOYSA-N 5-phenylpentyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCC1=CC=CC=C1 FBOYEYXUKAKVDL-UHFFFAOYSA-N 0.000 claims 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims 1
- UJTHMGMWSSOKMD-UHFFFAOYSA-N [4-(prop-2-enoyloxymethyl)phenyl]methyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=C(COC(=O)C=C)C=C1 UJTHMGMWSSOKMD-UHFFFAOYSA-N 0.000 claims 1
- 210000004087 cornea Anatomy 0.000 claims 1
- KUDUQBURMYMBIJ-UHFFFAOYSA-N ethylene glycol diacrylate Substances C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 23
- 239000000523 sample Substances 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000002202 Polyethylene glycol Substances 0.000 description 12
- 229920001223 polyethylene glycol Polymers 0.000 description 11
- 239000003999 initiator Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 5
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
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- 230000006399 behavior Effects 0.000 description 2
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- 238000013461 design Methods 0.000 description 2
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- 210000000613 ear canal Anatomy 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- DUDCYUDPBRJVLG-UHFFFAOYSA-N ethoxyethane methyl 2-methylprop-2-enoate Chemical compound CCOCC.COC(=O)C(C)=C DUDCYUDPBRJVLG-UHFFFAOYSA-N 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007779 soft material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QYKOGKTWYVIJNS-UHFFFAOYSA-N (1,2,2-tributylcyclohexyl) (1,2,2-tributylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C(=O)(OC1(C(CCCC1)(CCCC)CCCC)CCCC)OOC(=O)OC1(C(CCCC1)(CCCC)CCCC)CCCC QYKOGKTWYVIJNS-UHFFFAOYSA-N 0.000 description 1
- FCVJYKICQNLXAX-XPTLAUCJSA-N (2S)-1-oleoyl-2-methylglycero-3-phosphothionate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](OC)COP(O)(O)=S FCVJYKICQNLXAX-XPTLAUCJSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- MHXMVFDLNGKBSR-UHFFFAOYSA-N 2-hydroxyethyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C(=O)OCCO MHXMVFDLNGKBSR-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- CWVFILUMTNJKBN-UHFFFAOYSA-N 2-phenylmethoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCC1=CC=CC=C1 CWVFILUMTNJKBN-UHFFFAOYSA-N 0.000 description 1
- SUPSFAUIWDRKKZ-UHFFFAOYSA-N 5-methoxy-2h-benzotriazole Chemical compound C1=C(OC)C=CC2=NNN=C21 SUPSFAUIWDRKKZ-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
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- HLJYBXJFKDDIBI-UHFFFAOYSA-N O=[PH2]C(=O)C1=CC=CC=C1 Chemical compound O=[PH2]C(=O)C1=CC=CC=C1 HLJYBXJFKDDIBI-UHFFFAOYSA-N 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003855 balanced salt solution Substances 0.000 description 1
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- CJOKGGWAQWGINC-UHFFFAOYSA-N chloromethylbenzene;ethene Chemical compound C=C.ClCC1=CC=CC=C1 CJOKGGWAQWGINC-UHFFFAOYSA-N 0.000 description 1
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- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 210000000871 endothelium corneal Anatomy 0.000 description 1
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- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
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- UHFIMVQOGRRZRM-UHFFFAOYSA-N hydroxy-diphenyl-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(=S)(O)C1=CC=CC=C1 UHFIMVQOGRRZRM-UHFFFAOYSA-N 0.000 description 1
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- ZUQIVGCFGVFWNR-UHFFFAOYSA-N isocyanatoethane;2-methylprop-2-enoic acid Chemical compound CCN=C=O.CC(=C)C(O)=O ZUQIVGCFGVFWNR-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- RXRHXOLQBOFMDI-UHFFFAOYSA-N methoxymethane;2-methylprop-2-enoic acid Chemical compound COC.CC(=C)C(O)=O RXRHXOLQBOFMDI-UHFFFAOYSA-N 0.000 description 1
- 239000008239 natural water Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- A61L27/14—Macromolecular materials
-
- 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
- A61L27/14—Macromolecular materials
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
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- 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
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Description
本發明係關於一經改良之眼科與耳鼻喉科裝置材料。更特定地,本發明係關於柔軟、高折射率丙烯酸裝置材料,且該材料具有經改良之閃光抗性。
隨著近期在小切口白內障外科中的進展,係增加強調著眼於發展柔軟、可摺疊的材料上,該材料係適用於人工水晶體。一般地,該等材料係會落入於三種分類中之一種:水膠類(hydrogels)、矽樹脂(silicones)及丙烯酸聚合物(acrylics)。
一般地,水膠材料具有相對低之折射率,使該等水膠材料相較於其他材料為較不令人渴求的係因為較厚之水晶體,該水晶體係光學所需以達到一特定的折射力。傳統的矽樹脂材料相較於水膠類一般具有較高之折射率,但是在被以折疊式之置放於眼內之後,該矽樹脂材料係傾向爆發地展開。爆發地展開可潛在地損傷角膜內皮及/或破裂天生之水晶體囊(lens capsule)。丙烯酸材料係為令人渴求的,因為該等丙烯酸材料係典型地具有較高之折射率且相較於傳統的矽樹脂材料為較緩慢或可控制地展開。
美國專利案第5,290,892號揭露一高折射率之適合於使用作為一人工水晶體(intraocular lens)(“IOL”)材料之丙烯酸材料。該丙烯酸材料包含,如主要組份,二個芳基丙烯酸單體。該等以丙烯酸材料所製成之IOLs係可被捲繞或折疊以用於插入穿通過小切口。
美國專利案第5,331,073號亦揭露軟式丙烯酸材料。該等材料包含主要組份,二個丙烯酸單體,且該等單體係藉由其個別之同元聚合物的特性所界定。該第一單體係被界定為其中之同元聚合物具有至少約1.50之折射率。該第二單體係被界定為其中之同元聚合物具有少於約22℃之玻璃轉移溫度(glass transition temperature)。此些IOL材料一包含一交聯組份(cross-linking component)。額外地,此些材料可能選擇性地包含第四組份,其係不同於前三組分,該第四組份係衍生於親水單體。此些材料較佳地具有一總量少於約15%重量之親水組份。
美國專利案第5,693,095號揭露一可摺疊、高折射率的眼科水晶體材料,該材料含有至少約90wt.%之僅二主要成分,一係為芳香基丙烯酸疏水單體及一係為親水單體。該芳香基丙烯酸單體具有通式
其中,X為H或CH3
;M為0-6;Y為無物、O、S,或NR,其中R為H、CH3
、Cn
H2n+1
(n=1-10)、異-OC3
H7
、C6
H5
、或CH2
C6
H5
;且Ar為任何芳香環,該芳香環係可以CH3
、C2
H5
、n-C3
H7
、異-C3
H7
,OCH3
、C6
H11
、Cl、Br、C6
H5
、或CH2
C6
H5
而被未經取代或經取代。
在第’095號專利中被描述之水晶體材料係較佳地具有一介於-20至+25℃之玻璃轉移溫度(“Tg
”)。
可撓性人工水晶體可能被摺疊且被插入穿透過小切口。一般而言,軟式材料可能被變形為一較大範圍以致使該軟式材料可被插入穿透一逐漸減小的切口。軟式丙烯酸或異丁烯酸材料典型地不具有一強度、可撓性及不黏結表面特性之適合組合以容許欲被插入穿透過一切口之IOLs,該切口係與被需要用於矽氧樹脂IOLs之切口一樣小。
聚乙二醇(PEG)二甲基丙烯酸酯係被知悉為改善疏水丙烯酸配方之閃光抗性。參閱,例如,美國專利案第5,693,095、6,528,602、6,653,422及6,353,069號。聚乙二醇二甲基丙烯酸酯之濃度及分子量在閃光抗性上皆具有一影響力。一般而言,使用較高分子量之PEG二甲基丙烯酸酯(1000 MW)來產生具有在低PEG濃度(10-15wt%)時經改善之閃光抗性的共聚合物,如與較低分子量之PEG二甲基丙烯酸酯(<1000 WM)。無論如何,低PEG二甲基丙烯酸酯濃度係可欲求以維持高折射率的共聚合物。除了PEG二甲基丙烯酸酯係亦傾向以減少該產生之共聚合物的係數及應力強度。又,較高分子量之PEG二甲基丙烯酸酯係一般地與疏水丙烯酸單體不相溶。
經改善之軟式、可摺疊之丙烯酸裝置材料係特別適合用於如IOLs之用途,但作為諸如隱形眼鏡、角膜彌補物(keratoprostheses)、角膜環(corneal ring)或嵌體(inlays)、耳道通氣管(otological ventilation tubes)及鼻植入物之其他眼科或耳鼻喉科裝置亦被發現係有用的。此些聚合性材料包含二嵌段或三嵌段大分子單體,該等二嵌段或三嵌段大分子單體含有親水側鏈。
主題親水性側鏈大分子單體允許閃光抗性、低平衡水含量、高折射率IOLs之合成。使用具有親水性側鏈之大分子單體允許將高分子量親水性成分併入疏水性共聚物配方。相較於低分子量親水性聚合物之相當重量部分,較高分子量親水性成分係為較有效之閃光抗性成分。產生之親水成分濃度減少造成被減少的平衡水含量、較高之折射率及較小之塊狀人工水晶體,且該人工水晶體可透過一較小切口而被插入。
除非另外指出,所有組份量係以%(w/w)為主來呈現(“wt.%”)。
本發明之該等裝置材料係為共聚物,該等共聚物包含a)單效丙烯酸酯或甲基丙烯酸酯單體[1],b)雙效丙烯酸酯或甲基丙烯酸酯交聯體[2],及c)親水性側鏈之大分子單體[3](其可能為式[3a]、[3b]、[3c]、[3d]或[3e]之大分子單體)。該等裝置材料可能包含多於一單體[1]、多於一單體[2]、及多於一單體[3]。除非另外指出,關於各個成分係傾向包含數個相同式之單體或單分子單體及關於數量係傾向與各式之所有單體之總量相關。
其中B=-O(CH2
)n-、-(OCH2
CH2
)n-、-NH(CH2
)n
-、或-NCH3
(CH2
)n
-;R1
=H、CH3
、CH2
CH3
、或CH2
OH;n=0-12;A=C6
H5
或O(CH2
)m
C6
H5
,其中該C6
H5
基係選擇性地以-(CH2
)n
H、-O(CH2
)n
H、-CH(CH3
)2
、-C6
H5
、-OC6
H5
、-CH2
C6
H5
、F、Cl、Br、或I取代;且m=0-18;
其中R2
、R3
獨立地=H、CH3
、CH2
CH3
,或CH2
OH;W、W’獨立地=O(CH2
)d
、NH(CH2
)d
、NCH3
(CH2
)d
、O(CH2
)d
C6
H4
、O(CH2
CH2
O)d
CH2
、O(CH2
CH2
CH2
O)d
CH2
、O(CH2
CH2
CH2
CH2
O)d
CH2
,或無物;J=(CH2
)a
、O(CH2
CH2
O)b
、O、或無物,若W及W’=無物,則J≠無物;d=0-12;a=1-12;b=1-24;
其中對於式[3a]、[3b]、[3c]、[3d]及[3e](集體地,“式[3]”)e=1-50;X=-O-,NH-,-N(CH3
)-,-N(CH2
CH3
)-,或-N(C6
H5
)-;Y=-H,-(CH2
)p
OH,-CH2
CH2
N(CH3
)2
,-CH2
CH2
N(CH2
CH3
)2
,-CH2
CH(OH)CH2
OH,-(CH2
CH2
O)q
CH3
,-(CH2
CH2
O)q
H,-(CH2
CH2
O)q
C6
H5
,或p=1-12;q=1-230;T,T’獨立地=O(CH2
)d’
,NH(CH2
)d’
,NCH3
(CH2
)d’
,O(CH2
)d’
C6
H4
,O(CH2
CH2
O)d’
CH2
,O(CH2
CH2
CH2
O)d’
CH2
,O(CH2
CH2
CH2
CH2
O)d’
CH2,
或無物;K=(CH2
)a’
,O(CH2
CH2
O)b’,
O,或無物,若T and T’=無物,則K≠無物;d’=0-12;a’=1-12;b’=1-24;L=H,Cl,Br,-CH2
C(O)CH3
,CH2
C(O)C(CH3
)3
,-CH2
C(O)C6
H5
,-CH2
C(O)C6
H4
OH,-CH2
C(O)C6
H4
OCH3
,或-CH2
CH=CH2
;R4
,R5
獨立地=H,CH3
,CH2
CH3
,CH2
CH2
CH3
,CH(CH3
)2
,CH2
CH2
CH2
CH3
,或CH2
CH(CH3
)2
;R6
=-CO2
CH3
,-CO2
CH2
CH3
,-CN,或-CONHCH2
CH2
CH2
CH3
;R7
,R8
獨立地=H,CH3
,CH2
CH3
,或CH2
OH;M=-(CH2
)a”
-;及a”
=2-20。
較佳之式[1]單體係為該單體其中:B=-O(CH2
)n
-或-(OCH2
CH2
)n
-;R1
=-H或-CH3
;n=1-5;A=-C6
H5
、O(CH2
)m
C6
H5
;及m=0-4。
較佳之式[2]單體係為該單體其中:R2
、R3
獨立地=H或CH3
;W、W’獨立地=O(CH2
)d
、O(CH2
)d
C6
H4
,或無物;J=O(CH2
CH2
O)b
或無物,若W及W’=無物,則J≠無物;d=0-6;及b=1-10。
較佳之式[3]之大分子單體係為該大分子單體其中:e=2-40;X=-O-或-N(CH3
)-;Y=(CH2
CH2
O)q
CH3
,-(CH2
CH2
O)q
H,或-(CH2
CH2
O)q
C6
H5
;q=2-23;T,T’獨立地=O(CH2
)d’
或無物;K=O(CH2
CH2
O)b’
或無物,若T及T’=無物,則K≠無物;d’=0-6;b’=1-10;L=H,Cl,Br,-CH2
C(O)C6
H5
,-CH2
C(O)C6
H4
OH,-CH2
C(O)C6
H4
OCH3
,或-CH2
CH=CH2
;R4
,R5
獨立地=H,CH3
,或CH2
CH3
;R6
=-CO2
CH3
,-CO2
CH2
CH3
,-CN,或-CONHCH2
CH2
CH2
CH3
;R7
,R8
獨立地=H或CH3
;及a”=2-12。
最較佳之式[3]之大分子單體係為該大分子單體其中:e=5-30;X=-O-;Y=(CH2
CH2
O)q
CH3
;q=4-15;T,T’獨立地=O(CH2
)d’
,O(CH2
)d’
C6
H4
,或無物;K=O(CH2
CH2
O)b’
或無物,若T及T’=無物,則K≠無物;d’=0-6;b’=1-10;L=H,-CH2
C(O)C6
H5
,-CH2
C(O)C6
H4
OCH3
,或-CH2
CH=CH2
;R4
,R5
獨立地=H,CH3
,或CH2
CH3
;R6
=-CO2
CH3
,-CO2
CH2
CH3
,-CN,或-CONHCH2
CH2
CH2
CH3
;R7
,R8
獨立地=H或CH3
;及a”=2-12。
式[1]單體係被知悉且可藉由已知方法被製造。參閱,例如,美國專利案第5,331,073號及第5,290,892號。許多式[1]單體係為可自商業上不同的來源獲得。較佳的式[1]單體包括甲基丙烯酸芐酯、甲基丙烯酸2-苯乙酯、甲基丙烯酸3-苯丙酯、甲基丙烯酸4-苯丁酯、甲基丙烯酸5-苯戊酯、甲基丙烯酸2-苯氧乙酯、甲基丙烯酸2-(2-苯氧乙氧)乙酯、甲基丙烯酸2-芐氧基乙酯、甲基丙烯酸(2-(2-芐氧基)乙氧)乙酯、及甲基丙烯酸3-芐氧基丙酯,及其相對應之丙烯酸酯。
式[2]單體係被知悉且可藉由已知方法被製造。許多係為商業上可獲得的。較佳的式[2]單體包括乙二醇二甲基丙烯酸酯、二乙二醇二甲基丙烯酸酯、三乙二醇二甲基丙烯酸酯、1,6-己二醇二甲基丙烯酸酯、1,4-丁二醇二甲基丙烯酸酯、1,4-苯二甲醇二甲基丙烯酸酯、及其對應之丙烯酸酯。最較佳係為1,4-丁二醇二丙烯酸酯。
式[3]之大分子單體係被知悉且可藉由已知方法被製造。該等式[3]之大分子單體在一些例子中為商業上可獲得的且可藉由已知方法製造。式[3]之大分子單體可藉由將一可共聚基共價附著至一線形或分枝狀之丙烯酸或甲基丙烯酸聚合物的官能末端基。例如,羥基終端聚(甲基丙烯酸烷酯)可藉由陰離子聚合反應而被合成,該陰離子聚合反應係使用一含有被保護之羥基的起始劑,接著去保護係以例如甲基丙烯醯氯或甲基丙烯酸達成以產生大分子單體[3a]。終端羥基亦可與其他試劑反應,例如,甲基丙烯酸異氰酸乙酯或乙烯芐基氯,以產生終端可據合基。參閱,一般而言,美國專利案第6,221,991、3,862,077及3,842,059號,其完整內容係藉由參考而被併入。擇一地,聚合反應可以一醛而被終止且與接著與甲基丙烯醯氯反應以產生官能大分子單體[3b](參閱例如,美國專利案第6,221,991及5,391,628號)。
式[3c]大分子單體可亦藉由原子轉移自由基聚合反應(ATRP)情況而被製備。例如,羥基終端起始劑(溴異丁酸羥乙酯)可與鹵化銅(I)及溶解的胺配位基結合。此可被使用來起始丙烯酸酯或甲基丙烯酸酯之聚合反應。產生之羥基終端聚(丙烯酸酯)或聚(甲基丙烯酸酯)可接著與甲基丙烯醯氯或甲基丙烯酸異氰酸乙酯反應。參閱,一般而言,美國專利案第5,852,129、5,763,548、及5,789,487,及Neugebauer,etal.,“透過ATRP. A路徑以軟化彈性物之密度化接枝及二接枝PEO刷(Densely-grafted and double-grafted PEO brushes via ATRP. A route to soft elastomers),”Macromolecules
2003,36,6746-6755;Ishizu,et al.,“在水性介質中AB型刷-嵌段-刷兩親共聚物之聚集行為(Aggregation behaviors of AB-type brush-block-brush amphiphilic copolymers in aqueous media),”Journal of Materials Science
2004,39
,4295-4300;Kurjata, et al.,“聚[二甲基矽氧烷-嵌段-寡(乙二醇)甲基醚甲基丙烯酸酯]之合成:具有櫛狀嵌段之兩親共聚物(Synthesis of poly[dimethylsiloxane-block-oligo(ethylene glycol)methyl ether methacrylate]:an amphiphilic copolymer with a comb-like block),”Polymer
2004,15
,6111-6121;及Wang,et al.,“在周圍溫度下水性介質中甲氧基-封閉之寡(乙二醇)甲基丙烯酸酯的輕易原子轉移自由基聚合反應(Facile Atom Transfer Radical Polymerization of Methoxy-Capped Oligo(ethylene glycol)Methacrylate in Aqueous Media at Ambient Temperature),”Macromolecules
2000,33
,6640-6647。擇一地,催化鏈轉移劑可被用以與現存的聚合反應技術結合以產生甲基丙烯酸之式[3d]大分子單體。參閱例如,Norman,J. et al.Macromolecules 2002
,35,8954-8961,or Bon,S. A. F. et al.J. Polym. Sci.,Polym.Chem. 2000
,38
,2678。式[3e]大分子單體可被製造,例如,藉由在硫官能鏈轉移劑存在下聚合反應,接著藉由與甲基丙烯醯氯或甲基丙烯酸異氰酸乙酯反應。例如,參閱Chen,G.-F. et al.Macromolecules 1991
,24,2151。
本發明之共聚物材料含有單體[1]總量之量係為70至98%,且較佳為自80至95%。雙效交聯體[2]濃度可被命令為總濃度之0.5至3%,且較佳為自1至2%。
本發明之材料含有至少一[3]大分子單體。大分子單體[3]之總量係仰賴於所欲用於裝置材料的物理性質。本發明之共聚物材料含有至少0.5wt%之總量且可含有多如15%之大分子單體[3]。較佳地,該共聚物裝置材料將含有1-10wt%之大分子單體[3]。更較佳地,該共聚物裝置材料將含有1--5wt%之大分子單體[3]。最較佳地,該共聚物裝置材料將含有2-4wt%之大分子單體[3]。
本發明之共聚物裝置材料選擇性地含有一或二成份,且該成分係選自於由可聚合UV吸收體及可聚合著色劑所構成之群組。較佳地,本發明之裝置材料沒有含有其他成分,除了式[1]及[2]之單體、大分子單體[3]及該選擇性之可聚合UV吸收體及可聚合著色劑。
反應性UV吸收體係為人知悉的。一適合的反應性UV吸收體係為(2’-羥基-3’-甲基烯丙基-5’-甲基苯基)苯并三唑,商業上可獲得的如鄰-甲基烯丙基延納芬P(“oMVP”),來自Polysciences,Inc.,Warrington,Pennsylvania。UV吸收體係典型地存在於自約0.1-0.5%之量中。適合之反應性藍光吸收化合物包括於美國專利案第5,470,932號中所被描述之該些化合物。藍光吸收體係典型地在於自約0.1-0.5%之量中。當本發明之裝置材料被使用於製造IOLs時,本發明之裝置材料係較佳地含有一反應性UV吸收體及反應性著色劑。
為了形成本發明之裝置材料,被選擇之成分僅有[1]、[2]及[3]而無任何選擇性之成分,係使用自由基起始劑以起始藉由熱或放射作用之聚合反應而被結合且被聚合。該裝置材料係較佳地被聚合於氮氣下之脫氧聚丙烯模具中或在玻璃模具中。
適合之聚合反應起始劑包括熱起始劑及光起始劑。較佳之熱起始劑包括過氧無自由基起始劑,諸如(過氧-2-乙基)酸t-丁酯及過氧重碳酸二-(第三-丁基環己基)酯(商業上可獲得如來自Akzo Chemicals Inc.,Chicago,Illinois之16)。特別係在本發明之材料不含有藍光吸收發光團之情況中,較佳之光起始劑包括芐醯基磷氧化物(benzoylphosphine oxide)起始劑,諸如2,4,6-三甲基-苯甲醯基二苯基-磷氧化物,商業上可獲得的如來自BASF Corporation(Charlotte,North Carolina)之TPO。起始劑係典型地存在相等於約5%或更少之總配方量之量,且更較佳為少於2%之總配方。如習慣上用於計算組份量之目的,起始劑重量並不包括在配方重量%計算中。
特定的成份結合係於上被描述且任何額外組份之本體及數量係藉由被完成之裝置材料的所欲特性而被決定。在較佳之實施例中,本發明之裝置材料係被用於製造具有視直徑為5.5或6mm之IOLs,且該等IOLs被設計以欲被壓縮或延展及被插入通過2mm或更小之外科切口尺寸。例如,大分子單體[3]係與單官能甲基丙烯酸酯或甲基丙基酸酯單體[1]、一多官能結合甲基丙烯酸酯或甲基丙基酸酯交聯體[2]、一反應性UV吸收體及一反應性著色劑結合,且使用一自由基起始劑在適合之水晶體模具中共聚合。
裝置材料較佳地具有一在水合狀態為至少約1.50之折射率,且更較佳地至少約1.53,如藉由阿貝折射計(Abbe’s refractometer)在589nm(Na光源)及25℃所測量。由具有低於1.50之折射率的材料所製成之光學元件係必須較厚於由具有較高折射率之材料所製成之相同能力的光學元件。因此,以等同之機械特性及低於1.50之折射率之材料而製成的IOL光學元件係一般地需要相對較大之用於IOL植入的切口。
欲被包括在本發明之共聚物中的單體及大分子單體之特性係應被選擇以致於該共聚物具有不大於37℃之玻璃轉移溫度(Tg
),該溫度係為正常人體溫度。具有玻璃轉移溫度高於37℃之共聚物係不適合使用於可摺疊之IOLs;此類水晶體僅可在高於37℃溫度時被捲繞或折疊且將不可在正常人體溫度下被展開或攤開。使用具有玻璃轉移溫度稍為低於正常人體溫度且不大於正常室溫,例如約20-25℃之共聚物係被偏好的,為了使以此共聚物製造之IOLs可在室溫下方便地被捲繞或折疊。Tg
係藉由示差掃描熱析法以10℃/min而被測量,且係在熱通率曲線之轉移中點被決定。
對於IOLs及其他應用,本發明之材料必須存在足夠強度以允許以其製造之裝置被折疊或被操縱而不破裂。因此,本發明之共聚物將具有至少80%之延長性,較佳地至少100%,且最較佳地大於110%。此性質意指以此材料製成之水晶體一般地在被摺疊時將不會碎裂、撕裂或破裂。聚合物樣品之延長性係在啞鈴形張力測試樣品而被決定,該樣品係具有20mm之總長、4.88mm之抓握區域長、2.49mm之總寬、0.833mm之窄區段寬、8.83mm之內圓角半徑、及0.9mm之厚度。測試係在周圍狀況下使用具有50牛頓荷重元(Newton load cell)之英斯特材料試驗機(Instron Material Tester)(Model No. 4442或相等物件)而被操作於樣本上,抓握距離係被設定在14mm且十字頭速度係被設定在500mm/分鐘且樣品係被拖拉直到失敗。延長性(應力)係被描述如因為原有抓握距離喪失之移位部份。即使欲被測試之材料係為基本軟式彈性物,將該等彈性物裝載到英斯特機以易於使該等彈性物皺摺。為了移除在材料樣本中之鬆弛部分,一預裝載係被置放於樣本上。此協助減少該鬆弛部分且提供較一致之讀數。一旦樣本被預裝載至一所欲數值(典型地為0.03至0.05N),應力係被設定至零且測試開始。該係數係以在0%應力(“楊氏係數”)(“Young's Modulus”)、25%應力(“25%係數”)及100%應力(“25%係數”)之應力應變曲線的瞬時斜率來計算。
相較於其他材料,以本發明之眼科裝置材料所製成的IOLs對於閃光係較有抗力的。閃光係根據下列測試而被測量。閃光之存在係藉由將水晶體或圓盤置入一小玻璃瓶或已密封之玻璃腔室且加入去離子水或平衡鹽溶液而被測量。該小玻璃瓶或已密封之玻璃腔室係接續著被置入在預熱至45℃的水浴中。樣本係欲被維持在浴池中至少16小時且較佳地為24±2小時。該小玻璃瓶或已密封之玻璃腔室係接續著被冷卻至周圍溫度至少60分鐘且較佳地為90±30分鐘。樣品係以不同的角度或斜角光源來被視覺上地檢查以衡量清晰性。閃光之顯影係在周圍溫度下以使用50至200x倍率之光學顯微鏡而被實行。樣本係被判斷具有許多閃光,若在50-200x倍率時,有多如大約50至100%之閃光係在基於65重量%之丙烯酸2-苯基乙酯、30重量%之甲基丙烯酸2-苯基乙酯、3.2重量%之BDDA、及1.8重量%之OMPT的控制樣本中被觀察到。相似地,若有約10%或為相較於在控制樣本中被觀察量的較多閃光,樣本係被評價為具有少許的閃光。若有約為1%或為相較於在控制樣本中被觀察量的較多閃光,樣本係被評價為具有很少許的閃光。若在目鏡中被偵測到的閃光數目為零,樣本係被評鑑為沒有閃光。若在50-200x倍率下,在目鏡中被偵測到的閃光數目係少於約2/mm3
,樣本係被評價為實質上無閃光。偵測閃光經常是很困難的,特別係在有較多缺陷及碎片形成之表面或邊緣,因此樣品係遍佈水晶體全部體積而被逐行掃描,改變倍率層級(50-200x)、虹膜隔膜孔洞、及視野情況(皆使用明視野及暗視野情況)以企圖偵測閃光之存在。
本發明之共聚物係最較佳地具有0.5-3.0%之平衡水分含量(EWC)。EWC可能藉由乾燥及水合樣本重量之比較而被重力決定。首先,乾燥樣本的重量係被獲得,接著該樣本係被放置在適合的容器內且在指定溫度之去離子水中被平衡至少24小時。該樣品係接著自去離子水中被移除,過量表面之水係被移除,且該樣品係被秤重。EWC係藉由下列公式被決定:%EWC=[(wthyd
-wtdry
)/wthyd
]x 100。
本發明之裝置材料之被構成的IOLs可為任何設計,該設計係可被延展或擠壓入一小橫斷面,且該橫斷面係可適合透過2-mm的切口。例如,IOLs可被知悉如一件或多件之設計,且包含光學或觸覺元件。光學元件係為作為水晶體及觸覺元件之部份,且該水晶體及觸覺元件係附著至眼睛且係類似將眼睛放置在眼內其之適合位置的臂。該光學及觸覺元件可為相同或不同之材料。被稱作為多件之水晶體係因為該光學及觸覺元件係被分別地製造且接著該等觸覺元件係附著至眼睛。在單一件水晶體中,該光學及觸覺元件係以單一件材料所形成。仰賴該材料,觸覺元件係接著以該材料被切割、被釘板條來製造該IOLs。
除了IOLs,本發明之材料係亦適合供其他眼科或或耳鼻喉科裝置,諸如隱形眼鏡、角膜彌補物、角膜嵌體或環、耳道通氣管及鼻植入物之用途。
本發明將進一步藉由下列範例來闡述,其係欲為闡釋的,並非限制的。
所有單體、交聯體、及起始劑係自商業來源所購買。大分子單體[3](“polyPEG-MA”)係自聚(乙二醇)500單甲基醚單甲基丙烯酸酯(“PEG-MA 550”)所合成。二大分子單體[3]分子量係被使用:”polyPEG-MA 4.1k”(GPC Mn
4,112;Mw
/Mn
1.80;e=7(被計算如4112/550))且”polyPEG-MA 10.3k”(GPC Mn
10,300;Mw
/Mn
1.44;e=19)。甲基丙烯酸2-苯乙酯(PEMA)及甲基丙烯酸芐酯(BzMA)係在使用前先各通過鹼性氧化鋁且以N2
除氣。丙烯酸2-苯乙基(PEA)、丙烯酸芐酯(BzA)、1,4-丁二醇二甲基丙烯酸酯(BDDA)係在使用前先藉由管柱層析來純化。2,2-偶氮二異丁腈(AIBN)係在使用前自甲醇被再結晶。過氧重碳酸二-(4-第三-丁基環己基)酯(“16S”)、2-(2’-羥基-3’-第三-丁基-5’-(3”-(2’’’-羥基-3’’’-甲基丙烯醯氧基丙氧)丙氧)苯基)5-甲氧基-2H-苯并三唑(“UV13”),及鄰-甲基烯丙基延納芬(o-Methallyl Tinuvin P)(“oMVP”)係被使用於接收到時。
聚丙烯模具係在使用前於90℃下被真空除氣。該等模具係在除氣之後立即被置放在氮氣套手工作箱內。單體、大分子單體、交聯體及起始劑係如第1表中所指示之被結合。AIBN或16S起始劑係被加入(0.5-2.0wt.%),溶液係被完全混合接著被置放在低真空下以移除任何被困住之氣泡、以氮氣反沖、且立即地被置放在套手工作箱中。單體配方係使用配備有0.2-μm PTFE濾器之針筒而被分配入真空經除氣的聚丙烯模具內。經充滿之模具係被置放在對流烘箱1小時70℃,接著2小時110℃。產生之聚合物樣本係自模具中被移除且在回流丙酮中被萃取6小時、被潤洗且被空氣乾燥,接著被置放在70℃真空下至少15小時。應力特性、Tg
、EWC、閃光抗性及折射率係根據如上述之方法被決定。結果係被列於第2表內。
如第3表所顯示之共聚物,其含有不同尺寸之含有PEG添加劑(PEG-MA 550、polyPEG-MA 4.1k、及polyPEG-MA 10.3k)其係以如第1表中所述之方式而被製備。應力性質、EWC、閃光抗性及折射率係根據上述之方法而被決定。結果係被列於第4表內。
如第5表所顯示之共聚物,其含有不同分子量之polyPEG-MA添加劑:”PEG-MA 3570”(GPC Mn
3570;Mw
/Mn
1.42;e=6),”PEG-MA 4012”(GPC Mn
4141;Mw
/Mn
1.50;e=7)係以如第1表中所述之方式而被製備。應力性質、EWC、閃光抗性及折射率係根據上述之方法而被決定。結果係被列於第6表內。
本發明係藉由關於某些較佳實施例而被描述;無論如何,應該了解到本發明係可能被包含在其他特定形式或其變化而不背離其特別或基本特質。上述之實施例係因此被認為係欲在所有態樣中為說明的且非限制的,本發明之範圍係藉由被附加之申請專利範圍而被指示,而不是藉由前列敘述。
Claims (21)
- 一種聚合眼科或耳鼻喉科裝置材料,其包含a)70至98%(w/w)之式[1]之一單官能丙烯酸酯或甲基丙烯酸酯單體:
- 如申請專利範圍第1項之聚合裝置材料,其中對於該式[1]之單體:B=-O(CH2 )n -或-(OCH2 CH2 )n -;R1 =-H或-CH3 ;n=1-5;A=-C6 H5 、O(CH2 )m C6 H5 ;且m=0-4。
- 如申請專利範圍第1項之聚合裝置材料,其中對於該式[2]之單體:R2 、R3 獨立地=H或CH3 ;W、W’獨立地=O(CH2 )d 、O(CH2 )d C6 H4 ,或無物;J=O(CH2 CH2 O)b 或無物,若W及W’=無物,則J≠無物;d=0-6;且b=1-10。
- 如申請專利範圍第1項之聚合裝置材料,其中對於該式[3]之大分子單體:e=2-40;X=-O-或-N(CH3 )-;Y=(CH2 CH2 O)q CH3 、-(CH2 CH2 O)q H、或-(CH2 CH2 O)q C6 H5 ;q=2-23;T、T’獨立地=O(CH2 )d 、或無物;K=O(CH2 CH2 O)b 、或無物,若T及T’=無物,則K≠無物;d’=0-6;b’=1-10;L=H、Cl、Br、-CH2 C(O)C6 H5 、-CH2 C(O)C6 H4 OH、-CH2 C(O)C6 H4 OCH3 、或-CH2 CH=CH2 ;R4 、R5 獨立地=H、CH3 、或CH2 CH3 ;R6 =-CO2 CH3 、-CO2 CH2 CH3 、-CN、或-CONHCH2 CH2 CH2 CH3 ;R7 、R8 獨立地=H或CH3 ;且a”=2-12。
- 如申請專利範圍第4項之聚合裝置材料,其中對於該式[3]之大分子單體:e=5-30;X=-O-;Y=(CH2 CH2 O)q CH3 ;q=4-15;T、T’獨立地=O(CH2 )d’ 、O(CH2 )d’ C6 H4 、或無物;K=O(CH2 CH2 O)b’ 或無物,若T及T’=無物,則K≠無物;d’=0-6;b’=1-10;L=H、-CH2 C(O)C6 H5 、-CH2 C(O)C6 H4 OCH3 、或-CH2 CH=CH2 ;R4 、R5 獨立地=H、CH3 、或CH2 CH3 ;R6 =-CO2 CH3 、-CO2 CH2 CH3 、-CN、或-CONHCH2 CH2 CH2 CH3 ;R7 、R8 獨立地=H或CH3 ;且a”=2-12。
- 如申請專利範圍第1項之聚合裝置材料,其中該式[1]之單體係選自於由:甲基丙烯酸芐酯、甲基丙烯酸2-苯乙酯、甲基丙烯酸3-苯丙酯、甲基丙烯酸4-苯丁酯、甲基丙烯酸5-苯戊酯、甲基丙烯酸2-苯氧乙酯、甲基丙烯酸2-(2-苯氧乙氧)乙酯、甲基丙烯酸2-芐氧基乙酯、甲基丙烯酸(2-(2-芐氧基)乙氧)乙酯、甲基丙烯酸3-芐氧基丙酯、丙烯酸芐酯、丙烯酸2-苯乙酯、丙烯酸3-苯丙酯、丙烯酸4-苯丁酯、丙烯酸5-苯戊酯、丙烯酸2-苯氧乙酯、丙烯酸2-(2-苯氧乙氧)乙酯、丙烯酸2-芐氧基乙酯、丙烯酸(2-(2-芐氧基)乙氧)乙酯,及丙烯酸3-芐氧基丙酯所構成之群組。
- 如申請專利範圍第1項之聚合裝置材料,其中該式[2]之單體係選自於由:乙二醇二甲基丙烯酸酯、二乙二醇二甲基丙烯酸酯、三乙二醇二甲基丙烯酸酯、1,6-己二醇二甲基丙烯酸酯、1,4-丁二醇二甲基丙烯酸酯、1,4-苯二甲醇二甲基丙烯酸酯、乙二醇二丙烯酸酯、二乙二醇二丙烯酸酯、三乙二醇二丙烯酸酯、1,6-己二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、及1,4-苯二甲醇二丙烯酸酯所構成之群組。
- 如申請專利範圍第1項之聚合裝置材料,其中式[1]之單體之量為80至95%(w/w)。
- 如申請專利範圍第1項之聚合裝置材料,其中式[2]之單體之量為0.5至3%(w/w)。
- 如申請專利範圍第1項之聚合裝置材料,其中該親水性側鏈大分子單體之量為1至10%(w/w)。
- 如申請專利範圍第10項之聚合裝置材料,其中該親水性側鏈大分子單體之量為1至5%(w/w)。
- 如申請專利範圍第11項之聚合裝置材料,其中該親水性側鏈大分子單體之量為2至4%(w/w)。
- 如申請專利範圍第1項之聚合裝置材料,其中該親水性側鏈大分子單體係為一式[3a]之大分子單體。
- 如申請專利範圍第1項之聚合裝置材料,其中該親水性側鏈大分子單體係為一式[3b]之大分子單體。
- 如申請專利範圍第1項之聚合裝置材料,其中該親水性側鏈大分子單體係為一式[3c]之大分子單體。
- 如申請專利範圍第1項之聚合裝置材料,其中該親水性側鏈大分子單體係為一式[3d]之大分子單體。
- 如申請專利範圍第1項之聚合裝置材料,其中該親水性側鏈大分子單體係為一式[3e]之大分子單體。
- 如申請專利範圍第1項之聚合裝置材料,進一步包含一選自於由一可聚合UV吸收體及一可聚合著色劑所構成之群組之成分。
- 如申請專利範圍第18項之聚合裝置材料,其包含一0.1-5%(w/w)之可聚合UV吸收體及一0.01-0.5%(w/w)之可聚合著色劑。
- 一種眼科或耳鼻喉科裝置,其包含如申請專利範圍第1項之聚合裝置材料,其中該眼科或耳鼻喉科裝置係選自於由:人工水晶體、隱形眼鏡、角膜彌補物(keratoprostheses)、角膜嵌體(corneal inlays)或環、耳道通氣管(otological ventilation tubes)及鼻植入物所構成之群組。
- 如申請專利範圍第20項之眼科或耳鼻喉科裝置,其中該眼科或耳鼻喉科裝置係為一人工水晶體。
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KR (1) | KR101513131B1 (zh) |
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AT (1) | ATE510568T1 (zh) |
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TW (1) | TWI426932B (zh) |
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TWI513768B (zh) | 2011-06-01 | 2015-12-21 | Novartis Ag | 疏水性丙烯酸系眼內水晶體材料 |
TWI551646B (zh) | 2011-06-03 | 2016-10-01 | 諾華公司 | 疏水性丙烯酸系眼內水晶體材料 |
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