JP7442970B2 - 眼内レンズを調製するための材料 - Google Patents
眼内レンズを調製するための材料 Download PDFInfo
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- JP7442970B2 JP7442970B2 JP2018526180A JP2018526180A JP7442970B2 JP 7442970 B2 JP7442970 B2 JP 7442970B2 JP 2018526180 A JP2018526180 A JP 2018526180A JP 2018526180 A JP2018526180 A JP 2018526180A JP 7442970 B2 JP7442970 B2 JP 7442970B2
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- Prior art keywords
- acrylate
- methacrylate
- materials
- photosensitizer
- fluorescent
- Prior art date
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- 239000000463 material Substances 0.000 title claims description 289
- 239000003504 photosensitizing agent Substances 0.000 claims description 90
- 229920001577 copolymer Polymers 0.000 claims description 56
- 239000003795 chemical substances by application Substances 0.000 claims description 52
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 49
- 239000000178 monomer Substances 0.000 claims description 45
- 230000002209 hydrophobic effect Effects 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000007850 fluorescent dye Substances 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 230000009477 glass transition Effects 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 11
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 10
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000012986 modification Methods 0.000 claims description 9
- 230000004048 modification Effects 0.000 claims description 9
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 7
- 239000012567 medical material Substances 0.000 claims description 7
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 3
- GDIYMWAMJKRXRE-UHFFFAOYSA-N (2z)-2-[(2e)-2-[2-chloro-3-[(z)-2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,3,3-trimethylindole Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=CC=C1C(Cl)=C(C=CC=2C(C3=CC=CC=C3[N+]=2C)(C)C)CCC1 GDIYMWAMJKRXRE-UHFFFAOYSA-N 0.000 claims description 2
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-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
- UZFPOOOQHWICKY-UHFFFAOYSA-N 3-[13-[1-[1-[8,12-bis(2-carboxyethyl)-17-(1-hydroxyethyl)-3,7,13,18-tetramethyl-21,24-dihydroporphyrin-2-yl]ethoxy]ethyl]-18-(2-carboxyethyl)-8-(1-hydroxyethyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoic acid Chemical compound N1C(C=C2C(=C(CCC(O)=O)C(C=C3C(=C(C)C(C=C4N5)=N3)CCC(O)=O)=N2)C)=C(C)C(C(C)O)=C1C=C5C(C)=C4C(C)OC(C)C1=C(N2)C=C(N3)C(C)=C(C(O)C)C3=CC(C(C)=C3CCC(O)=O)=NC3=CC(C(CCC(O)=O)=C3C)=NC3=CC2=C1C UZFPOOOQHWICKY-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- UJKPHYRXOLRVJJ-MLSVHJFASA-N CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C Chemical class CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C UJKPHYRXOLRVJJ-MLSVHJFASA-N 0.000 claims description 2
- KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000298 carbocyanine Substances 0.000 claims description 2
- 239000013522 chelant Substances 0.000 claims description 2
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical class C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 2
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 claims description 2
- RGPLGPBQJOQFJS-UHFFFAOYSA-L disodium;3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC=C([O-])C=C1OC1=CC([O-])=CC=C21 RGPLGPBQJOQFJS-UHFFFAOYSA-L 0.000 claims description 2
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 claims description 2
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 2
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 2
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 2
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 claims description 2
- 229960004293 porfimer sodium Drugs 0.000 claims description 2
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 2
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 2
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 claims description 2
- 229950003776 protoporphyrin Drugs 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 2
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 claims description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims 2
- YMHPNLUYVDEYCI-UHFFFAOYSA-N (6'-hydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) 2-methylprop-2-enoate Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(OC(=O)C(=C)C)=CC=C21 YMHPNLUYVDEYCI-UHFFFAOYSA-N 0.000 claims 1
- VYLDMXSRCVCHNE-UHFFFAOYSA-N (6'-hydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) prop-2-enoate Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(OC(=O)C=C)C=C1OC1=CC(O)=CC=C21 VYLDMXSRCVCHNE-UHFFFAOYSA-N 0.000 claims 1
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- 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
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- A—HUMAN NECESSITIES
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- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/048—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- 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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
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- A—HUMAN NECESSITIES
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- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2240/00—Manufacturing or designing of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
- A61F2240/001—Designing or manufacturing processes
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
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- A—HUMAN NECESSITIES
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- 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
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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
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/16—Materials or treatment for tissue regeneration for reconstruction of eye parts, e.g. intraocular lens, cornea
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
- B29K2105/0002—Condition, form or state of moulded material or of the material to be shaped monomers or prepolymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
- B29K2995/0018—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds having particular optical properties, e.g. fluorescent or phosphorescent
- B29K2995/0035—Fluorescent
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- G—PHYSICS
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- 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
Description
かかる材料(特に眼医材料)は、親水性アクリレートモノマーおよび疎水性アクリレートモノマーを含むアクリレートモノマーの共重合によって調製され、
親水性モノマーと疎水性モノマーとのモル比が、20:80~80:20、好ましくは30:70~70:30、より好ましくは40:60~60:40であり、
a特性:35℃における含水率が、5~15重量%、好ましくは6~13重量%、より好ましくは7~12重量%、さらに好ましくは8~11重量%、特に9~11重量%、および
b特性:35℃における屈折率(ウェット状態)が、1.49~1.54、好ましくは1.49~1.53、より好ましくは1.50~1.52
といった特定の特性を有する材料に関する。
上記の式中、R1は、HまたはC1-6のアルキルであり、好ましくはHまたはCH3であり、
R2は、直鎖状、分岐状、飽和もしくは不飽和のC1-20のアルキルまたはC6-20のアリールアルキル、あるいは、直線状もしくはC6-20のヘテロアリールアルキルであり;
Xは、O、SまたはNR4であってよく(R4は、Hもしくは、直鎖状、分岐状、飽和もしくは不飽和のC1-20のアルキルまたはC6-20のアリールアルキルまたはC6-20のヘテロアリールアルキルまたはC3-20のヘテロシクリルアルキルである);
R3は、CnH2n+1Om(mまたはnは0であるか、あるいは1よりも大きい整数から選択される、m≦n)または、C3-20のヘテロシクリルアルキルまたはC3-20のシクロアルキルである。
式中、R1は、HまたはC1-6のアルキルであり、好ましくはHまたはCH3であり、
R5は、直鎖状、分岐状、飽和もしくは不飽和のC1-20のアルキルまたはC6-20のアリールアルキル、またはC6-20のヘテロアリールアルキルまたはC6-20のヘテロシクリルアルキルまたはC3-20のシクロアルキルであり;
Yは、HまたはZ-R6であってよく(Zは、存在または非存在なものであり得、OもしくはSなどのヘテロ原子から選択され得る)、
R6は、C6-20のアリールアルキルまたはC6-20のヘテロアリールアルキルである。
a特性:35℃における含水率が、5~15重量%、好ましくは6~13重量%、より好ましくは7~12重量%、および
b特性:35℃における屈折率(水和物、hydrate)が、1.49~1.54、好ましくは1.49~1.53、より好ましくは1.50~1.52。
本発明の材料(例えば、眼内レンズを調製するための材料)は、親水性モノマーと疎水性モノマーとのモル比は、20:80~80:20、好ましくは25:75~75:25、より好ましくは30:70~70:30、さらに好ましくは35:65~65:35、さらに好ましくは40:60~60:40、さらに好ましくは45:55~55:45であり、さらには約50:50となっている。いずれの理論に拘束されるわけではないが、コポリマーの屈折率式は、
であって、
式中,
Viは、各要素の体積分率であり、niは、各要素の屈折率であり、水飽和後の親水性アクリレート材料の屈折率は、以下の式
をおよそ適用することができる。式中、Vwは、水の体積分率(およそ水含率)、nwは、水の屈折率、npは、乾燥アクリレートポリマーの屈折率である。これに基づいて、本発明の材料では上記含水率および屈折率を有するように疎水性モノマーと親水性モノマーとの割合が調整される。
コポリマー材料との蛍光剤および/または感光剤の組合せモードは、
- 蛍光剤および/または感光剤が、コポリマー材料の形成時における重合に関与する(participate in)、
- 蛍光剤および/または感光剤が、コポリマー材料の形成時にて物理的分散(physical dispersion)によってコポリマー材料に加えられる、
- 蛍光剤および/または感光剤が、表面グラフト(surface grafting)または表面改質(surface modification)によってコポリマー材料の表面に固定される、ならびに/または
- 蛍光剤および/または感光剤が、表面コーティング(surface-coating)によってコポリマー材料の表面に固定される、
から成る群から選択される。
ここでいう、重合可能な基は、例えば、ビニル、アリル、ブチレン、アクリルオキシ、メタクリルオキシ、アクリルアミド、メタクリルアミド、ビニルエーテルの基、アルキニル、ヒドロキシ、メルカプト、アミノ、イミノ、カルボキシ、アンヒドライド(無水物,
anhydride)、アルデヒド基、イソシアネート基、シロキサン基、エポキシ、含窒素環状基、および、それに類するものであってよい。
1)重合可能なモノマーをオプションの添加剤(例えば、熱架橋剤、開始剤、UV吸収剤、およびそれに類するもの)と混合する工程、ならびに
2)蛍光剤および/または感光剤を加えて、それを溶解させ、重合を行う工程。
1)重合可能モノマーを、熱開始剤、架橋剤および/またはUV吸収剤と混合する工程、
2)蛍光剤および/または感光剤を溶解させるべく、蛍光剤および/または感光剤を加える工程、
3)上記2)で得られた反応系をモールドに入れる工程、
4)重合(水浴重合など)を行う工程、ならびに
5)乾燥機にて重合を再度行う工程。
1)重合可能モノマーを、架橋剤、熱開始剤、UV吸収剤などのオプションの添加剤と混合し、コポリマー材料を得るべく重合を行う工程、
2)蛍光剤および/または感光剤を溶解させるべく、蛍光剤および/または感光剤を加え(例えば、重合性モノマーなどの適当なアジュバントと共に蛍光剤および/または感光剤を溶解させ)、次いで、グラフト重合などの重合または表面変性または転写プリンティングを行う工程。
1)重合可能モノマーを、熱開始剤、架橋剤および/またはUV吸収剤と混合する工程、
2)上記1)で得られた反応系をモールドに移す工程、
4)重合(水浴重合など)を行う工程、
5)乾燥機で重合を再度行う工程、
6)蛍光剤および/または感光剤を溶解させる工程(例えば、適当な重合可能性モノマーとともに、蛍光剤および/または感光剤を溶解させる工程)
7)上記で得られた系をグラフト重合などの重合または表面変性または転写プリンティングに付す工程。
1)適当なコポリマー材料を得る工程、ならびに
2)蛍光剤および/または感光剤、例えば、適当な溶媒に溶解した蛍光剤および/または感光剤を、コポリマー材料の表面にコートする工程。
EA:エチルアクリレート
EMA:エチルメタクリレート
BA:ブチルアクリレート
HEMA:ヒドロキシエチルメタクリレート
HEA:ヒドロキシエチルアクリレート
PEA:フェニルエチルアクリレート
PEMA:フェニルエチルメタクリレート
POEA:フェノキシエチルアクリレート
BMA:ベンジルエチルメタクリレート
EOEMA:エトキシエチルメタクリレート
EOEOEA:エトキシエトキシエチルアクリレート
Y28:青色光吸収剤
RI:35℃で測定された水和後の屈折率値
ウォータ%:含水率
Tg:材料(乾燥状態)のガラス転移温度
調製された材料を用いて眼内レンズを得る処理を行った。かかる材料を室温でターンさせ、調製されたポリマー材料を約3mmの厚さおよび約16mmの直径を有するIOLビレットへと分割し、次いで、シングルポイントダイヤモンド旋削(OPTOFORM)上でターンさせて形状付けを行う。形状付けの後、眼内レンズを研磨媒体でポリッシュ(または磨き)に付し、生理食塩水内へとすすぎに付すことによって表面は洗浄されて水和化し、それによって、含水バランスが得られて眼内レンズを得ることができた。得られた眼内レンズは減菌の生理食塩水内で貯留された。
本実施例では、材料の分光透過率(spectral transmittance)を評価すべく眼内レンズの分光透過率を測定する方法が例示される。可視領域における実施例6および22の材料から形成された眼内レンズの透過率が、分光光度計を用いて測定される。かかる分光光度計では、機器がMAPADAのUV-3300タイプのUV-Vis分光光度計であり、300~1100nmの波長走査範囲を有している。分光透過率曲線を図3および図4に示す。実施例6は、紫外線吸収タイプであり、実施例22は青色濾過されるタイプであって、有害な紫外線および青色光の濾過が為される。可視光領域における平均分光透過率は95%よりも大きく、分光透過率の特性として優れている。よって、眼内レンズの調製に適している。
本実施例では、材料のガラス転移温度のための試験方法が例示される。実施例5の材料のガラス転移温度は、米国のTAインスツルメンツ(TA Instruments)の示差走査熱量測定分析器(Parallax Scanning Calorimetry Analyzer)のモデルQ20を用いて調べた。なお、サンプルは10mgであり、昇温速度10℃/分および温度走査範囲-35℃~60℃とした。ソフトウェアによる解析により、材料のガラス転移温度が24.12℃であることが示された。試験結果を図5に示す。材料は、室温よりも僅かに上回る温度で軟らかくなり、ブランク内へとパンチングするのに適している。また、材料は、室温よりも僅かに下回る温度で硬くなり、眼内レンズへの加工が容易になる。そして、材料は比較的穏やかなガラス転移温度を有しており、眼内レンズの大量生産に資する。
本実施例では、材料の屈折率を測定する方法が示されている。アッベ(Abb)の屈折計を用い、ウェット状態および乾燥状態で実施例21の材料の屈折率を調べた。アッベの屈折計は恒温水浴に接続され、試験時の恒温水浴の温度は35℃に設定された。乾燥された材料の屈折率(すなわち、乾燥状態の材料の屈折率)は、平衡後、当業者に既知の試験法を用いて調べた。乾燥状態における実施例21の材料の屈折率の値は1.5158であった。同じ材料片を生理食塩水で水和させ、35℃の恒温インキュベーターに7日間置いた。表面の湿り気については即座に拭き取った後、乾燥状態の場合と同様の方法で屈折率を測定した。ウエット状態における実施例21の材料の屈折率は1.5038であった。
本発明の目的は、眼内レンズの生産に用いるのに適した媒体水含量を有する材料を開発することである。本実施例では、材料の含水率を測定する方法が例示される。調製された材料は、35℃にて生理食塩水に置かれ、平衡に至るまで十分に水和させた。材料から水を除去した後、その表面の湿り気は即座に拭き取って、ウェット重量m1を測定により得た。次いで、材料を60℃にて真空オーブンに置いて、一定の重量に至るまで十分に乾燥させ、乾燥重量m2を測定により得た。その水和平衡状態の材料の含水率は以下の式に従って計算される。
含水率=(m1-m2)/m1
実施例21の材料の含水率は、上記手法に従って測定された結果、その値は5.1%であった。
本実験例では、材料内のグリスタリングのための試験方法が与えられる。材料のグリスタリングは、ALCON AcrySof IOLSに影響を与える主たる要因である。グリスタリングは、材料中にホールまたは空砲・液胞(vacuole)があることを意味している。重度のグリスタリングは、眼内レンズの光学性能に影響を与え、重度の術後の問題をもたらす。本発明の材料に対して、その内側のグリスタリングに関する試験を行った。
本実施例では、材料のシリコーン・オイルの吸着特性の試験方法および試験結果が例示される。まず、染料(オイルレッド)を適当な量のエタノールに溶解させ、濾過することで、オイルレッド・エタノール溶液を得た。かかる溶液をシリコーン・オイルに加え、6時間撹拌して均一な混合物を得た。染料を含んだシリコーン・オイルを70℃にて一晩置き、エタノールを除去した。試験に付されるサンプルは、BSS溶液に24時間浸し、除去して排液し、染料を含むシリカゲルにおき、3時間浸し、シリコーン・オイルで排液し、再度BSS溶液に1時間置いた。写真を取り、吸収度を解析した。
本実施例では、材料表面へのカルシウム沈着(calcium deposition)に関する試験法および試験結果が例示される。1994年、Jensenらは、白内障患者の11のケースが、外科手術中またはその術後の早期において眼内レンズの表面に沈着があったことを初めて報告している。X線回折試験の結果、沈着物はカルシウムヒドロキシアパタイトを含んでいることが分かった。その後の調査では、親水性材料が疎水性材料よりもカルシウム沈着により資することが示され、親水性眼内レンズの治療用途でみられる典型的な問題となっている。本発明の材料シートおよび比較材料をヒドロキシアパタイトの懸濁液に浸し、24時間の吸着に付した後、BSSに1時間浸した。そして、材料をアリザリンレッド溶液中に置いて、写真を取り、汚れ状態を観察した。アリザリンレッドで特に汚れが付けられた領域は、ヒドロキシアパタイト吸着領域であり、それは、カルシウム沈着領域に相当する。
材料の機械的性質の試験を例示すべく、実施例6の材料を用いた。実施例6で得られた材料は、7日間、35℃で生理食塩水において水和に付した。十分な水和に付した後、ATSM D638表のタイプIVに従うようにパンチを用い、材料を標準形状へとパンチングに付した。
実施例27で処理された全ての眼内レンズを模擬外科手術に際して順次インプラントに付した。白内障の外科手術のための眼内レンズのインプラント・システム一式(インプランターおよび導入ヘッドを含むインプラント・システム)を使用した。導入ヘッドの端部としては、外科的切開のサイズに応じて異なるサイズを有するものを用いた。各モデルのパラメーターを表3に示す。インプランターは、導入ヘッドのモデルに適合させるものである。具体的な操作は次の通りである。まず、適当な量の粘弾性剤を導入ヘッド内に注入した。ピンセットを用いて眼内レンズを摘まみ導入ヘッド内に入れ、導入ヘッドのマークにまで押し込んだ。そして、導入ヘッドをプッシャーに取り付け、外科手術時の操作プラクティスを模擬すべく約5分間待った。最後に、生理食塩水で満たされたベッセル内へとインプラントし、押込み注入(push-injection)のプロセスがスムーズであるか否か、眼内レンズがスムーズに折畳み状態から開放された否か、導入ヘッドが損傷したか否かについて記録した。インプラント試験の間、室温環境は25~30℃に制御され、粘弾性剤温度は2~8℃に制御され、生理食塩水は19~25℃に制御された。
Claims (13)
- 適した含水率および適した屈折率を有する微小切開眼内レンズの製造用の眼医材料であって、
親水性アクリレートモノマーおよび疎水性アクリレートモノマーを含むアクリレート含有の重合性モノマーの共重合によって調製されるコポリマーを含んで成り、
親水性アクリレートモノマーと疎水性アクリレートモノマーとのモル比が、42.5:57.5~45.5:54.5であり、
a特性:35℃における含水率が、5~15重量%、および
b特性:35℃における屈折率(水和物)が、1.49~1.54
c特性:10~35℃のガラス転移温度(DSCによって測定される乾燥状態)
を有し、
180%よりも大きい破断伸び(水和物)を有し、破断強度(水和物)が2.5MPaよりも大きく、
親水性アクリレートモノマーは、ヒドロキシエチルメタクリレート、ヒドロキシエチルアクリレート、ヒドロキシプロピルメタクリレート、ヒドロキシプロピルアクリレート、または、これら物質の混合物から成る群から選択され、
疎水性アクリレートモノマーは、メチルメタクリレート、エチルメタクリレート、エチルアクリレート、ブチルメタクリレート、ブチルアクリレート、ヘキシルメタクリレート、ヘキシルアクリレート、イソプロピルメタクリレート、イソプロピルアクリレート、イソブチルメタクリレート、イソブチルアクリレート、tert-ブチルメタクリレート、tert-ブチルアクリレートから成る群から選択される1つの疎水性アクリレートモノマーと、
フェニルメタクリレート、フェニルアクリレート、フェニルエチルメタクリレート、フェニルエチルアクリレート、フェノキシエチルメタクリレート、フェノキシエチルアクリレート、ベンジルメタクリレート、ベンジルアクリレート、フェノキシエチルアクリレートから成る群から選択される他の疎水性アクリレートモノマーと
の組み合わせ、または、これら物質の混合物から成る群から選択される、材料。 - 15~35℃のガラス転移温度(DSCによって測定される乾燥状態)を有する、請求項1に記載の材料。
- 少なくとも1つの蛍光剤および/または少なくとも1つの感光剤を更に含んで成り、
コポリマーとの蛍光剤および/または感光剤の組合せモードは、
- 蛍光剤および/または感光剤が、コポリマー材料の形成時における重合に関与する、
- 蛍光剤および/または感光剤が、コポリマー材料の形成時にて物理的分散によってコポリマー材料に加えられる、
- 蛍光剤および/または感光剤が、表面グラフトまたは表面改質によってコポリマー材料の表面に固定される、ならびに/または
- 蛍光剤および/または感光剤が、表面コーティングによってコポリマー材料の表面に固定される、
から成る群から選択される、請求項1に記載の材料。 - 蛍光剤が、フルオレセイン(ナトリウム)、シアニン蛍光色素、フルオレセイン・イソチオシアネート、蛍光特性を有するローダミン物質、蛍光特性を有するランタニドキレート、P-フィコエリトリン(PE)、酵素作用に応じて蛍光を生じる物質、例えばポリピダクロロフィリン(PerCP)、ヨウ化プロピジウム、およびそれらの混合物から成る群から選択される、請求項3に記載の材料。
- 感光剤が、インドールモノシアニン(モノメチンシアニン)、インドールカルボシアニン(トリメチンシアニン)、インドールジカルボシアニン(ペンタメチンシアニン)、インドールトリカルボシアニン(ヘプタメチンシアニン)、トリカルボシアニン色素、ベンゾインドールセミシアニン色素、インドールスクアリリウム色素、クロロフィル誘導体、フェオフィチン、フェオホルビドaおよびその誘導体、ジヒドロポルフィンe6およびその誘導体、プルプリン18、ジヒドロポルフィンp6およびその誘導体、ジヒドロポルフィンfおよびその誘導体、プロトポルフィリンおよびその誘導体、ヘマトポルフィリン誘導体(HpD)、ポルフィマーナトリウム、フォトカルシノリン(PSD-007)、ナノゴールド、ナノタングステンオキサイド、ナノ銅スルフィド、ナノ鉄オキサイド、ナノニッケルカーバイド、ナノモリブデンオキサイド、フルオレセインO-アクリレート、および、フルオレセインO-メタクリレート、およびそれらの混合物から成る群から選択される、請求項3に記載の材料。
- 35℃における含水率が、6~13重量%である、請求項1に記載の材料。
- 35℃における含水率が、7~12重量%である、請求項1に記載の材料。
- 35℃における屈折率(水和物)が、1.49~1.53である、請求項1に記載の材料。
- 35℃における屈折率(水和物)が、1.50~1.52である、請求項1に記載の材料。
- 15~30℃のガラス転移温度(DSCによって測定される乾燥状態)を有する、請求項2に記載の材料。
- 20~25℃のガラス転移温度(DSCによって測定される乾燥状態)を有する、請求項2に記載の材料。
- 請求項1~11のいずれかに記載の微小切開眼内レンズの製造用の眼医材料から成る医療デバイスまたは医療具。
- 医療デバイスまたは医療具の調製における請求項1~11のいずれかに記載の微小切開眼内レンズの製造用の眼医材料の使用。
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