JP2005181729A - コンタクトレンズ材料 - Google Patents
コンタクトレンズ材料 Download PDFInfo
- Publication number
- JP2005181729A JP2005181729A JP2003423038A JP2003423038A JP2005181729A JP 2005181729 A JP2005181729 A JP 2005181729A JP 2003423038 A JP2003423038 A JP 2003423038A JP 2003423038 A JP2003423038 A JP 2003423038A JP 2005181729 A JP2005181729 A JP 2005181729A
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- meth
- weight
- acrylate
- contact lens
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000463 material Substances 0.000 title claims abstract description 48
- 239000000178 monomer Substances 0.000 claims abstract description 107
- 229920001577 copolymer Polymers 0.000 claims abstract description 62
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000001301 oxygen Substances 0.000 claims abstract description 33
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 230000035699 permeability Effects 0.000 claims abstract description 29
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 28
- 238000010521 absorption reaction Methods 0.000 claims abstract description 19
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000003431 cross linking reagent Substances 0.000 claims description 20
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 abstract description 9
- 230000005540 biological transmission Effects 0.000 abstract description 2
- -1 trimethylsiloxy Chemical group 0.000 description 78
- 238000006116 polymerization reaction Methods 0.000 description 31
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 30
- 239000012965 benzophenone Substances 0.000 description 30
- 239000000975 dye Substances 0.000 description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 13
- 239000007983 Tris buffer Substances 0.000 description 9
- AHNYHYYIECFEQY-UHFFFAOYSA-N 2-phenylethenylsilicon Chemical compound [Si]C=CC1=CC=CC=C1 AHNYHYYIECFEQY-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- SOEDHYUFNWMILE-UHFFFAOYSA-N naphthalen-1-yl prop-2-enoate Chemical compound C1=CC=C2C(OC(=O)C=C)=CC=CC2=C1 SOEDHYUFNWMILE-UHFFFAOYSA-N 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 229940076442 9,10-anthraquinone Drugs 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 210000004087 cornea Anatomy 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010559 graft polymerization reaction Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- FVFMYDCFRDYUCF-UHFFFAOYSA-N methyl(2-phenylethenyl)silane Chemical compound C[SiH2]C=CC1=CC=CC=C1 FVFMYDCFRDYUCF-UHFFFAOYSA-N 0.000 description 3
- 238000009832 plasma treatment Methods 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DSTUKHPLWATFCG-UHFFFAOYSA-N (2-benzoylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C(=O)C1=CC=CC=C1 DSTUKHPLWATFCG-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- FIONWRDVKJFHRC-UHFFFAOYSA-N trimethyl(2-phenylethenyl)silane Chemical compound C[Si](C)(C)C=CC1=CC=CC=C1 FIONWRDVKJFHRC-UHFFFAOYSA-N 0.000 description 2
- UEPYASQNDSOKDY-UHFFFAOYSA-N trimethyl-(1-methylsilyl-2-phenyl-2-trimethylsilyloxyethenoxy)silane Chemical compound C[SiH2]C(O[Si](C)(C)C)=C(O[Si](C)(C)C)c1ccccc1 UEPYASQNDSOKDY-UHFFFAOYSA-N 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- MPXHLFZVRCWKOH-UHFFFAOYSA-N (2-benzoyl-4-tert-butylphenyl) prop-2-enoate Chemical compound CC(C)(C)c1ccc(OC(=O)C=C)c(c1)C(=O)c1ccccc1 MPXHLFZVRCWKOH-UHFFFAOYSA-N 0.000 description 1
- PTVHJARVSMLXLE-UHFFFAOYSA-N (4-ethenylphenyl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=C(C=C)C=C1 PTVHJARVSMLXLE-UHFFFAOYSA-N 0.000 description 1
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- IMDHDEPPVWETOI-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2,2,2-trichloroethanone Chemical compound CC(C)(C)C1=CC=C(C(=O)C(Cl)(Cl)Cl)C=C1 IMDHDEPPVWETOI-UHFFFAOYSA-N 0.000 description 1
- FMSBDDXYTGRROM-UHFFFAOYSA-N 1-amino-4-(3-ethenylanilino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC(C=C)=C1 FMSBDDXYTGRROM-UHFFFAOYSA-N 0.000 description 1
- NETQWKMHDYXHPQ-UHFFFAOYSA-N 1-amino-4-[(2-ethenylphenyl)methylamino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NCC1=CC=CC=C1C=C NETQWKMHDYXHPQ-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- SMSKIVCCLIQXFD-UHFFFAOYSA-N 1-tert-butyl-3-ethenylbenzene Chemical compound CC(C)(C)C1=CC=CC(C=C)=C1 SMSKIVCCLIQXFD-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- CLISWDZSTWQFNX-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)F CLISWDZSTWQFNX-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- FDTLQXNAPKJJAM-UHFFFAOYSA-N 2-(3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=NC2=CC=CC=C2C=C1O FDTLQXNAPKJJAM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- BEBXWONSZVHSNT-UHFFFAOYSA-N 2-[[4-(methylamino)-9,10-dioxoanthracen-1-yl]amino]ethyl 4-ethenylbenzoate Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(NC)=CC=C1NCCOC(=O)C1=CC=C(C=C)C=C1 BEBXWONSZVHSNT-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-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
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- KLQVCADYSBUVAV-UHFFFAOYSA-N 4-[(2,4-dimethylphenyl)diazenyl]-5-methyl-2-phenyl-4h-pyrazol-3-one Chemical compound CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=C(C)C=C1C KLQVCADYSBUVAV-UHFFFAOYSA-N 0.000 description 1
- PIGJEEDUNYKCTJ-UHFFFAOYSA-N 6-chloro-4-n-(3-ethenylphenyl)-2-n-[(4-nitrophenyl)diazenyl]-2-n-phenyl-1,3,5-triazine-2,4-diamine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N=NN(C=1N=C(NC=2C=C(C=C)C=CC=2)N=C(Cl)N=1)C1=CC=CC=C1 PIGJEEDUNYKCTJ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-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
- RLIJMSWBSOVKOI-UHFFFAOYSA-N C=CC(C=C1)=CC=C1C(N)=O.O=C(C1=CC=CC=C11)C(C=CC=C2)=C2C1=O Chemical compound C=CC(C=C1)=CC=C1C(N)=O.O=C(C1=CC=CC=C11)C(C=CC=C2)=C2C1=O RLIJMSWBSOVKOI-UHFFFAOYSA-N 0.000 description 1
- GFUDSKDJKVHGJH-UHFFFAOYSA-N C=CC(N)=O.OC(C=CC=C1)=C1N=NC(C=C(C=C1)C2=CC=CC=C2)=C1O Chemical compound C=CC(N)=O.OC(C=CC=C1)=C1N=NC(C=C(C=C1)C2=CC=CC=C2)=C1O GFUDSKDJKVHGJH-UHFFFAOYSA-N 0.000 description 1
- KCHQUUDXHFZQJF-UHFFFAOYSA-N CC(C=C1)=CC=C1N=NC(C=C1)=CC=C1O.C=CC(N)=O Chemical compound CC(C=C1)=CC=C1N=NC(C=C1)=CC=C1O.C=CC(N)=O KCHQUUDXHFZQJF-UHFFFAOYSA-N 0.000 description 1
- IWPYCXLTCGFDNJ-UHFFFAOYSA-N CS(C)c1ccc(C=C)cc1 Chemical compound CS(C)c1ccc(C=C)cc1 IWPYCXLTCGFDNJ-UHFFFAOYSA-N 0.000 description 1
- 208000032544 Cicatrix Diseases 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
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- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
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Landscapes
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Abstract
【解決手段】特定のシリコーン含有モノマーを含む共重合成分を重合して得られる共重合体からなるコンタクトレンズ材料であって、該共重合体中に残留する未重合モノマー成分の、該共重合体に対する残留量の合計が、3.5重量%以下であり、該共重合体の酸素透過係数が、130×10-11(cm2/sec)・(mLO2/(mL・mmHg))以上であり、かつ該共重合体の吸水率が、0.3重量%以下であるコンタクトレンズ材料。
【選択図】なし
Description
トリス(トリメチルシロキシ)シリルスチレン(以下、TMSiSt)45重量部、トリフルオロエチルメタクリレート(以下、3FEMA)45重量部、エチレングリコールジメタクリレート(以下、EDMA)10重量部を混合した。得られた混合物に重合開始剤として2,2’−アゾビス(2,4−ジメチルバレロニトリル)(以下、V−65)を、この混合物100重量部に対して0.3重量部添加し、良く撹拌して混合した。
配合を表1に示すように変更した以外は、実施例1と同様にして共重合体を作製、切削加工を施し、得られた試験片の物性を以下の方法にしたがい測定をした。その結果を表1に示す。
配合を表1に示すように変更した以外は、実施例1と同様にして共重合体を調製、切削加工を施し、得られた試験片の物性を以下の方法にしたがい測定をした。その結果を表1に示す。
表1にしたがい配合された共重合成分をガラス製試験管に注入し、窒素置換したのち密栓し、循環式恒温水槽に入れ、35℃で40時間予備重合を行ったのち、50℃へ昇温して8時間加熱保持した。その後、循環式恒温乾燥器中で、50〜120℃まで10℃/1.5時間の昇温速度で加熱し、重合を完結させた(重合条件B)。
<酸素透過係数(Dk)>
GTG(GAS to GAS)ANALYZER(REHDERDEVELOPMENT COMPANY(米国)製)を用いて、測定時間2分、温度35℃にて測定し、その得られた測定値を、ISO 9912−2にて規格化されたメニコンEX(Dk値=64)を用いて換算して、Dk値を求め、その結果を表1に示した。なお、Dk値は、酸素透過係数の値[(cm2/sec)・(mLO2/(mL・mmHg))]を意味し、とくに、酸素透過係数の値に10-11を乗じた数値である。
厚さ0.5mmの試験片(乾燥したもの)を10枚一組として、各一組毎にその重量(A[g])を測定し、蒸留水の入ったサンプル瓶に、25℃の温度にて24時間浸漬した後、試験片の湿潤重量(B[g])を測定した。下式によって吸水率を算出した。その結果は、表1に示した。
吸水率(%)={(B−A)/A}×100
FDA GUIDANCE DOCUMENT FOR CLASS III CONTACT LENSES APRIL 1989 p.18 「Leachable and residual monomers」を参考に、直径12mm、厚み0.5mmのプレート1枚をアセトニトリル5mLで50℃、72時間抽出し、高速液体クロマトグラフィー(HPLC;高速液体クロマトグラフ:WATERS社製2695セパレーションモジュール;検出器:WATERS社製フォトダイオードアレイ検出器996;カラム:野村化学株式会社製 Develosil ODS HG−5 Length 250mm×I.D.4.6mm)を用いて、各共重合成分の標準液から作成された検量線により、アセトニトリル抽出液中の各未重合モノマー成分の濃度を定量し、下式により未重合モノマー成分の残留量を算出した。HPLCの分析条件は、移動相の初期設定値をアセトニトリル/蒸留水=30/70とし、測定開始と同時に移動相の組成を連続的に変化させ(リニアグラジエント)、30分後にアセトニトリル/蒸留水=100/0になるように設定した。そして、分析終了までアセトニトリル/蒸留水=100/0で保持した。なお、検出波長は210nm、流量は1.0mL/分、オーブン温度は40℃、打込み量は20μLとした。
=(アセトニトリル抽出液中の各未重合モノマー濃度(10-6g/mL)×5(mL)
/プレート重量(g))×100
株式会社明石製作所製ロックウェルスーパーフィッシャル硬度計を使用し、荷重30kg、圧子1/4インチ(約0.64cm)により、温度25℃、相対湿度50%の恒温恒湿室内で、直径12.0mm、厚さ4.0mmの試験片について測定した。
ダイヤモンドバイトを用いた切削加工機を使用して、CL形状試験片への加工を行った。加工性および加工後の試料片表面状態を目視で観察し、下記評価基準に基づいて評価した。
(評価基準)
○:容易にレンズへ加工・研磨できる
△:加工可能であるが、若干毟れが発生する
×:チッピング様の毟れがひどく加工が困難
得られた試験片の両面を研磨し、布やティッシュペーパーなどで擦ったのち、試験片の表面状態を目視で観察し、下記評価基準に基づいて評価した。
(評価基準)
○:ほとんど傷はみられない
△:若干の傷がみられた
×:傷が多くみられた(弱い力で擦っても容易に傷付いた)
重合したボタン形状の共重合体を切削加工し、一定規格(ベースカーブ:7.90mm、パワー:−10.0D(ディオプトリー)、レンズ直径:9.2mm)のレンズを作製した。湿潤状態(界面活性剤含有CLケア用品)および乾燥状態で、40℃の過酷条件で6ヶ月間保存したのちに、ベースカーブおよびレンズ直径の測定を行った。
Claims (6)
- 前記共重合体が、前記一般式(I)で表されるシリコーン含有モノマーおよびアルキル基の炭素数が1〜6であり、かつ該アルキル基の少なくとも1つの水素原子がフッ素原子で置換されているアルキル(メタ)アクリレートから実質的になるモノマー成分ならびに架橋剤を重合して得られる請求項1記載のコンタクトレンズ材料。
- 前記共重合体が、前記一般式(I)で表されるシリコーン含有モノマーを45〜70重量部、前記アルキル(メタ)アクリレートを20〜45重量部および架橋剤を5〜15重量部含む共重合成分を重合して得られる請求項2記載のコンタクトレンズ材料。
- 前記共重合体が、さらに紫外線吸収剤および/または色素を含有する請求項1、2または3記載のコンタクトレンズ材料。
- 前記共重合体が、前記モノマー成分および架橋剤を、40〜120℃で、30分から5時間、重合して得られる請求項1、2、3または4記載のコンタクトレンズ材料。
- 請求項1、2、3、4または5記載のコンタクトレンズ材料からなるコンタクトレンズ。
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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JP2003423038A JP4502638B2 (ja) | 2003-12-19 | 2003-12-19 | コンタクトレンズ材料 |
ES04820642T ES2397072T3 (es) | 2003-12-19 | 2004-11-24 | Material de lente de contacto |
CN2004800378804A CN1894620B (zh) | 2003-12-19 | 2004-11-24 | 隐形眼镜材料 |
US10/583,506 US20070149699A1 (en) | 2003-12-19 | 2004-11-24 | Contact lens material |
EP04820642A EP1696257B1 (en) | 2003-12-19 | 2004-11-24 | Contact lens material |
PCT/JP2004/017393 WO2005062108A1 (ja) | 2003-12-19 | 2004-11-24 | コンタクトレンズ材料 |
US12/483,431 US20090247662A1 (en) | 2003-12-19 | 2009-06-12 | Contact Lens Material |
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JP2003423038A JP4502638B2 (ja) | 2003-12-19 | 2003-12-19 | コンタクトレンズ材料 |
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JP2010026629A Division JP2010111880A (ja) | 2010-02-09 | 2010-02-09 | コンタクトレンズ材料の製造方法 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010539263A (ja) * | 2007-09-13 | 2010-12-16 | コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 改良された着色ポリマー製造方法 |
WO2011004800A1 (ja) * | 2009-07-08 | 2011-01-13 | 株式会社メニコン | ハイブリッドソフトコンタクトレンズ、この製造方法及び水和処理方法 |
WO2013002409A1 (ja) * | 2011-06-30 | 2013-01-03 | Hoya株式会社 | プラスチックレンズ |
JP2013172764A (ja) * | 2012-02-23 | 2013-09-05 | Toray Ind Inc | 低含水性軟質デバイス、低含水性軟質デバイス用組成物およびこれらの製造方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02198415A (ja) * | 1989-01-28 | 1990-08-06 | Menikon:Kk | 眼用レンズ材料 |
JPH03122612A (ja) * | 1989-10-05 | 1991-05-24 | Menikon:Kk | 眼用レンズ材料 |
JPH05313106A (ja) * | 1992-05-08 | 1993-11-26 | Menicon Co Ltd | 眼用レンズ材料 |
JPH0764029A (ja) * | 1993-08-23 | 1995-03-10 | Menicon Co Ltd | コンタクトレンズ |
JPH1180274A (ja) * | 1997-09-12 | 1999-03-26 | Menicon Co Ltd | 光学材料 |
JPH11133201A (ja) * | 1997-10-29 | 1999-05-21 | Menicon Co Ltd | 光学材料 |
JPH11269232A (ja) * | 1998-03-24 | 1999-10-05 | Menicon Co Ltd | 光学材料 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2515010B2 (ja) * | 1989-01-26 | 1996-07-10 | 株式会社メニコン | 眼用レンズ材料 |
-
2003
- 2003-12-19 JP JP2003423038A patent/JP4502638B2/ja not_active Expired - Lifetime
-
2004
- 2004-11-24 CN CN2004800378804A patent/CN1894620B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02198415A (ja) * | 1989-01-28 | 1990-08-06 | Menikon:Kk | 眼用レンズ材料 |
JPH03122612A (ja) * | 1989-10-05 | 1991-05-24 | Menikon:Kk | 眼用レンズ材料 |
JPH05313106A (ja) * | 1992-05-08 | 1993-11-26 | Menicon Co Ltd | 眼用レンズ材料 |
JPH0764029A (ja) * | 1993-08-23 | 1995-03-10 | Menicon Co Ltd | コンタクトレンズ |
JPH1180274A (ja) * | 1997-09-12 | 1999-03-26 | Menicon Co Ltd | 光学材料 |
JPH11133201A (ja) * | 1997-10-29 | 1999-05-21 | Menicon Co Ltd | 光学材料 |
JPH11269232A (ja) * | 1998-03-24 | 1999-10-05 | Menicon Co Ltd | 光学材料 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010539263A (ja) * | 2007-09-13 | 2010-12-16 | コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 改良された着色ポリマー製造方法 |
JP2014196500A (ja) * | 2007-09-13 | 2014-10-16 | ジーイーオー スペシャルティ ケミカルズ ユーケー リミティド | 改良された着色ポリマー製造方法 |
WO2011004800A1 (ja) * | 2009-07-08 | 2011-01-13 | 株式会社メニコン | ハイブリッドソフトコンタクトレンズ、この製造方法及び水和処理方法 |
US8662663B2 (en) | 2009-07-08 | 2014-03-04 | Menicon Co., Ltd. | Hybrid soft contact lens, and production method and hydration treatment method thereof |
WO2013002409A1 (ja) * | 2011-06-30 | 2013-01-03 | Hoya株式会社 | プラスチックレンズ |
CN103649821A (zh) * | 2011-06-30 | 2014-03-19 | Hoya株式会社 | 塑料透镜 |
JPWO2013002409A1 (ja) * | 2011-06-30 | 2015-02-23 | Hoya株式会社 | プラスチックレンズ |
JP2013172764A (ja) * | 2012-02-23 | 2013-09-05 | Toray Ind Inc | 低含水性軟質デバイス、低含水性軟質デバイス用組成物およびこれらの製造方法 |
Also Published As
Publication number | Publication date |
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CN1894620A (zh) | 2007-01-10 |
CN1894620B (zh) | 2012-09-26 |
JP4502638B2 (ja) | 2010-07-14 |
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