JP5568310B2 - コンタクトレンズ - Google Patents
コンタクトレンズ Download PDFInfo
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- JP5568310B2 JP5568310B2 JP2009537624A JP2009537624A JP5568310B2 JP 5568310 B2 JP5568310 B2 JP 5568310B2 JP 2009537624 A JP2009537624 A JP 2009537624A JP 2009537624 A JP2009537624 A JP 2009537624A JP 5568310 B2 JP5568310 B2 JP 5568310B2
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- 239000000203 mixture Substances 0.000 claims abstract description 77
- 239000002904 solvent Substances 0.000 claims abstract description 76
- 239000000178 monomer Substances 0.000 claims abstract description 75
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 30
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 29
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 29
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 29
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 11
- 229920001519 homopolymer Polymers 0.000 claims abstract description 10
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 26
- -1 trimethylsilylmethacryloxypropyl Chemical group 0.000 claims description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- 150000003138 primary alcohols Chemical group 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 6
- 230000002209 hydrophobic effect Effects 0.000 claims description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 6
- 239000007870 radical polymerization initiator Substances 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 150000003333 secondary alcohols Chemical class 0.000 claims description 4
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 4
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 description 19
- 239000000017 hydrogel Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000007983 Tris buffer Substances 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- 150000003926 acrylamides Chemical class 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920001477 hydrophilic polymer Polymers 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000007975 buffered saline Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- KAKFZMMRKBQABS-UHFFFAOYSA-N trimethyl(silyloxysilyloxy)silane Chemical compound C[Si](C)(C)O[SiH2]O[SiH3] KAKFZMMRKBQABS-UHFFFAOYSA-N 0.000 description 2
- 229960000834 vinyl ether Drugs 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- GKMAGVRDFXUTDS-UHFFFAOYSA-N (1-carbamoyloxy-2,3-dihydroxypropyl) 2-methylprop-2-enoate Chemical compound C(N)(OC(C(O)CO)OC(C(=C)C)=O)=O GKMAGVRDFXUTDS-UHFFFAOYSA-N 0.000 description 1
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
- CTXUTPWZJZHRJC-UHFFFAOYSA-N 1-ethenylpyrrole Chemical compound C=CN1C=CC=C1 CTXUTPWZJZHRJC-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-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
- GZEXHGDBYMTBCP-UHFFFAOYSA-N 2-carbamoyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(N)=O GZEXHGDBYMTBCP-UHFFFAOYSA-N 0.000 description 1
- BQBSIHIZDSHADD-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1,3-oxazole Chemical compound C=CC1=NCCO1 BQBSIHIZDSHADD-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- ZIFLDVXQTMSDJE-UHFFFAOYSA-N 3-[[dimethyl-[3-(2-methylprop-2-enoyloxy)propyl]silyl]oxy-dimethylsilyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)CCCOC(=O)C(C)=C ZIFLDVXQTMSDJE-UHFFFAOYSA-N 0.000 description 1
- NWBTXZPDTSKZJU-UHFFFAOYSA-N 3-[dimethyl(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)C NWBTXZPDTSKZJU-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- JUNHSANWMFPFEW-UHFFFAOYSA-N CC(C)C(NOC(C(C)=C)=O)=O Chemical compound CC(C)C(NOC(C(C)=C)=O)=O JUNHSANWMFPFEW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- BOJYOZQNQLXPOU-UHFFFAOYSA-N n-[3-[[3-(prop-2-enoylamino)propyl-bis(trimethylsilyloxy)silyl]oxy-bis(trimethylsilyloxy)silyl]propyl]prop-2-enamide Chemical compound C=CC(=O)NCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](CCCNC(=O)C=C)(O[Si](C)(C)C)O[Si](C)(C)C BOJYOZQNQLXPOU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- NFYUPFDCZPKNQJ-UHFFFAOYSA-N tris(trimethylsilyl) trimethylsilyloxysilyl silicate Chemical compound C[Si](C)(C)O[SiH2]O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C NFYUPFDCZPKNQJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Images
Classifications
-
- 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
-
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- General Health & Medical Sciences (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Tumbler Switches (AREA)
- Auxiliary Devices For And Details Of Packaging Control (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
(A)溶剤を除いた全組成物の重量に対して少なくとも10重量%の少なくとも一種の式Iに示すシリコーン含有モノマー、
(B)溶剤を除いた全組成物の重量に対して少なくとも10重量%の3−メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン、
(C)N−ビニルピロリドン、及び、
(D)少なくとも一種の他の非イオン性親水性モノマー
の反応生成物を含む組成により形成され、(A)と(B)の総量は溶剤を除いた全組成物の重量に対して少なくとも20重量%であり、且つ、該N−ビニルピロリドン(NVP)の量は該反応生成物においてポリビニルピロリドン(PVP)ホモポリマーが含まれる量であるコンタクトレンズを提供するものである。随意に、反応混合物は、さらに溶剤を除いた全組成物の重量に対して3重量%までのアクリル酸又はメタクリル酸を含んでいても良い。
(A)溶剤を除いた全組成物の重量に対して少なくとも10重量%の少なくとも一種の上記式Iに示すシリコーン含有モノマー、
(B)溶剤を除いた全組成物の重量に対して少なくとも10重量%の3−メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン、
(C)溶剤を除いた全組成物の重量に対して20〜60重量%のN−ビニルピロリドン、
(D)溶剤を除いた全組成物の重量に対して2〜10重量%の少なくとも一種の他の非イオン性親水性モノマー、
(E)溶剤を除いた全組成物の重量に対して0.2〜2重量%のフリーラジカル重合開始剤、及び、
(F)溶剤を除いた全組成物の重量に対して0.2〜5重量%の架橋剤、の反応生成物を含む組成により形成され、(A)と(B)の総量は溶剤を除いた全組成物の重量に対して少なくとも20重量%であるコンタクトレンズを提供するものである。随意に、反応混合物は、さらに溶剤を除いた全組成物の重量に対して3重量%までのアクリル酸又はメタクリル酸を含んでいても良い。
(A)と(B)の総量は溶剤を除いた全組成物の重量に対して少なくとも20重量%で、
(A)溶剤を除いた全組成物の重量に対して少なくとも10重量%の少なくとも一種の式Iに示すシリコーン含有モノマー、
(B)溶剤を除いた全組成物の重量に対して少なくとも10重量%の3−メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン、
(C)溶剤を除いた全組成物の重量に対して20〜60重量%のN−ビニルピロリドン、
(D)溶剤を除いた全組成物の重量に対して2〜10重量%の少なくとも一種の他の非イオン性親水性モノマー、
(E)溶剤を除いた全組成物の重量に対して0.2〜2重量%のフリーラジカル重合開始剤、及び、
(F)溶剤を除いた全組成物の重量に対して0.2〜5重量%の架橋剤に、
反応物の重量に対して15〜30重量%の少なくとも一種の第一級アルコールを含む溶剤を加えて混合する工程、
混合物をコンタクトレンズの型に流し込む工程、及び、
反応混合物を硬化させてコンタクトレンズを形成する工程を含む、コンタクトレンズの製造方法を提供することである。随意に、その反応混合物は、さらに溶剤を除いた全組成物の重量に対して3重量%までのアクリル酸又はメタクリル酸を含んでいても良い。
コンタクトレンズを表1に示す組成を有する様々なモノマー混合物を反応させて作製した。すべてのコンタクトレンズにおいて、エタノールと酢酸エチルの50:50混合物を溶剤として用いた。
例11〜13は、共溶剤として同量のエタノールとデカノールを用いた際の組成物におけるメタクリル酸の影響を示したものである。
さらに、表5に示す組成を有する様々なモノマー混合物を反応させてコンタクトレンズを作製した。上記例1〜10と同様の方法でコンタクトレンズを作製し、得られたコンタクトレンズについて同様の測定を行った。例33〜37において、湿潤したレンズの直径とベースカーブはOptimecJCFタイプで測定した。
Claims (14)
- (A)溶剤を除いた全組成物の重量に対して少なくとも10重量%の少なくとも一種の式Iに示すシリコーン含有モノマー、
(B)溶剤を除いた全組成物の重量に対して少なくとも10重量%の3−メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン、
(C)溶剤を除いた全組成物の重量に対して30〜60重量%のN−ビニルピロリドン、及び、
(D)少なくとも一種の他の非イオン性親水性モノマー、
の反応生成物を含む組成により形成され、(A)と(B)の総量は溶剤を除いた全組成物の重量に対して少なくとも20重量%であり、且つ、該N−ビニルピロリドン(NVP)の量は該反応生成物においてポリビニルピロリドン(PVP)ホモポリマーが含まれる量であることを特徴とする、コンタクトレンズ。
- 前記N−ビニルピロリドンの量が、溶剤を除いた全組成物の重量に対して40〜60重量%であることを特徴とする、請求項1に記載のコンタクトレンズ。
- (A)溶剤を除いた全組成物の重量に対して少なくとも10重量%の少なくとも一種の式Iに示すシリコーン含有モノマー、
(B)溶剤を除いた全組成物の重量に対して少なくとも10重量%の3−メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン、
(C)溶剤を除いた全組成物の重量に対して30〜60重量%のN−ビニルピロリドン、
(D)溶剤を除いた全組成物の重量に対して2〜10重量%の少なくとも一種の他の非イオン性親水性モノマー、
(E)溶剤を除いた全組成物の重量に対して0.2〜2重量%のフリーラジカル重合開始剤、及び、
(F)溶剤を除いた全組成物の重量に対して0.2〜5重量%の架橋剤
の反応生成物を含む組成により形成され、(A)と(B)の総量は溶剤を除いた全組成物の重量に対して少なくとも20重量%であることを特徴とする、コンタクトレンズ。
- (D)成分が少なくとも2−ヒドロキシエチルメタクリレート及びN,N−ジメチルアクリルアミドのうち一つを含むことを特徴とする、請求項1乃至3のいずれか一項に記載のコンタクトレンズ。
- さらに溶剤を除いた全組成物の重量に対して3重量%までのアクリル酸又はメタクリル酸を含むことを特徴とする、請求項1乃至4のいずれか一項に記載のコンタクトレンズ。
- (A)成分がトリメチルシリルメタクリロキシプロピル(ポリジメチルシロキサン)を含むことを特徴とする、請求項1乃至5のいずれか一項に記載のコンタクトレンズ。
- 前記フリーラジカル重合開始剤(E)がAZBNであることを特徴とする、請求項3に記載のコンタクトレンズ。
- 前記架橋剤(F)がテトラエチレングリコールジメタクリレートであることを特徴とする、請求項3又は7に記載のコンタクトレンズ。
- (A)と(B)の総量は溶剤を除いた全組成物の重量に対して少なくとも20重量%で、
(A)溶剤を除いた全組成物の重量に対して少なくとも10重量%の少なくとも一種の式Iに示すシリコーン含有モノマー、
(B)溶剤を除いた全組成物の重量に対して少なくとも10重量%の3−メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン、
(C)溶剤を除いた全組成物の重量に対して30〜60重量%のN−ビニルピロリドン、
(D)溶剤を除いた全組成物の重量に対して2〜10重量%の少なくとも一種の他の非イオン性親水性モノマー、
(E)溶剤を除いた全組成物の重量に対して0.2〜2重量%のフリーラジカル重合開始剤、及び、
(F)溶剤を除いた全組成物の重量に対して0.2〜5重量%の架橋剤に、
反応物の重量に対して15〜30重量%の少なくとも一種の第一級アルコールを含む溶剤を加えて混合する工程、
混合物をコンタクトレンズの型に流し込む工程、及び、
反応混合物を硬化させてコンタクトレンズを形成する工程を含むことを特徴とする、コンタクトレンズの製造方法。
- 前記溶剤が第二級及び第三級アルコールを含まないことを特徴とする、請求項9に記載のコンタクトレンズの製造方法。
- 前記溶剤がエタノール及び/又はデカノール及び/又はプロパノールを含むことを特徴とする、請求項9又は10に記載のコンタクトレンズの製造方法。
- 前記溶剤が少なくとも一種の第一級アルコールと、少なくとも一種の当該第一級アルコールよりもより疎水性の高い追加の溶剤を含み、当該追加の溶剤の量が溶剤の20〜50重量%であることを特徴とする、請求項9乃至11のいずれか一項に記載のコンタクトレンズの製造方法。
- 前記追加の溶剤が、ヘキサノール、オクタノール、デカノール及び酢酸エチルのうちの1又は2以上であることを特徴とする、請求項12に記載のコンタクトレンズの製造方法。
- 前記溶剤がエタノールと、ヘキサノール、オクタノール、デカノール及び酢酸エチルのうちの少なくとも一つの混合物を含むことを特徴とする、請求項13に記載のコンタクトレンズの製造方法。
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HK1130905A1 (en) | 2010-01-08 |
US20140171544A1 (en) | 2014-06-19 |
KR20090089856A (ko) | 2009-08-24 |
KR101532394B1 (ko) | 2015-06-29 |
WO2008061992A3 (en) | 2008-07-17 |
DK2087384T3 (da) | 2010-11-15 |
ES2347839T3 (es) | 2010-11-04 |
DE602007008753D1 (de) | 2010-10-07 |
WO2008061992A2 (en) | 2008-05-29 |
US20130015595A1 (en) | 2013-01-17 |
JP2010510550A (ja) | 2010-04-02 |
GB0623299D0 (en) | 2007-01-03 |
ATE479121T1 (de) | 2010-09-15 |
CN101542321B (zh) | 2015-05-27 |
CN101542321A (zh) | 2009-09-23 |
MY145978A (en) | 2012-05-31 |
US8703891B2 (en) | 2014-04-22 |
EP2087384A2 (en) | 2009-08-12 |
EP2087384B1 (en) | 2010-08-25 |
US20100048847A1 (en) | 2010-02-25 |
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