AU654520B2 - Rigid contact lenses with improved oxygen permeability - Google Patents
Rigid contact lenses with improved oxygen permeability Download PDFInfo
- Publication number
- AU654520B2 AU654520B2 AU10088/92A AU1008892A AU654520B2 AU 654520 B2 AU654520 B2 AU 654520B2 AU 10088/92 A AU10088/92 A AU 10088/92A AU 1008892 A AU1008892 A AU 1008892A AU 654520 B2 AU654520 B2 AU 654520B2
- Authority
- AU
- Australia
- Prior art keywords
- methacrylate
- poly
- weight
- dimethylsiloxane
- reaction product
- 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.)
- Ceased
Links
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000001301 oxygen Substances 0.000 title claims abstract description 34
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 34
- 230000035699 permeability Effects 0.000 title claims abstract description 26
- 229920000642 polymer Polymers 0.000 claims abstract description 87
- 239000000178 monomer Substances 0.000 claims abstract description 67
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 54
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 40
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 19
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 7
- 238000004132 cross linking Methods 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- 229920001577 copolymer Polymers 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- -1 poly(dimethylsiloxane) Polymers 0.000 claims description 133
- 229920002554 vinyl polymer Polymers 0.000 claims description 75
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 54
- 239000007795 chemical reaction product Substances 0.000 claims description 53
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 34
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 33
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 31
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 30
- 125000005442 diisocyanate group Chemical group 0.000 claims description 25
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 22
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 22
- 239000012948 isocyanate Substances 0.000 claims description 22
- 150000002513 isocyanates Chemical class 0.000 claims description 22
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 19
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 229920005862 polyol Polymers 0.000 claims description 16
- 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 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 229920000768 polyamine Polymers 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 229920006295 polythiol Polymers 0.000 claims description 9
- APAUNQLFVGBQQW-UHFFFAOYSA-N (1,2,2-trimethylcyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(C)CCCCC1(C)C APAUNQLFVGBQQW-UHFFFAOYSA-N 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- 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 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 5
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 4
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 3
- JCMFXEIQKSSNTG-UHFFFAOYSA-N 3-[[3-(2-methylprop-2-enoyloxy)propyl-bis(trimethylsilyloxy)silyl]oxy-bis(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCOC(=O)C(C)=C JCMFXEIQKSSNTG-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 229910018540 Si C Inorganic materials 0.000 claims description 3
- 150000003926 acrylamides Chemical class 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 229940063557 methacrylate Drugs 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229920001296 polysiloxane Polymers 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000005457 ice water Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 7
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 229910007933 Si-M Inorganic materials 0.000 description 4
- 229910008318 Si—M Inorganic materials 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- UJKWLAZYSLJTKA-UHFFFAOYSA-N edma Chemical compound O1CCOC2=CC(CC(C)NC)=CC=C21 UJKWLAZYSLJTKA-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DABQKEQFLJIRHU-UHFFFAOYSA-N 2-Propenoic acid, 2-methyl-, 3,3,5-trimethylcyclohexyl ester Chemical compound CC1CC(OC(=O)C(C)=C)CC(C)(C)C1 DABQKEQFLJIRHU-UHFFFAOYSA-N 0.000 description 3
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- ZTUGCJNAJJDKDC-UHFFFAOYSA-N n-(3-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCO ZTUGCJNAJJDKDC-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- KDAKDBASXBEFFK-UHFFFAOYSA-N 2-(tert-butylamino)ethyl prop-2-enoate Chemical compound CC(C)(C)NCCOC(=O)C=C KDAKDBASXBEFFK-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 2
- LLTAGRBKLBDOIZ-UHFFFAOYSA-N 3-(tert-butylamino)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCNC(C)(C)C LLTAGRBKLBDOIZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 150000001298 alcohols Chemical class 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-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
- 239000004202 carbamide Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003754 machining Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- CNNKPIGLYRJQRS-UHFFFAOYSA-N (1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl) prop-2-enoate Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(OC(=O)C=C)C(F)(F)C1(F)F CNNKPIGLYRJQRS-UHFFFAOYSA-N 0.000 description 1
- WTKDTRXVTIKPCO-UHFFFAOYSA-N (1-isocyanato-2-methylpropan-2-yl) prop-2-enoate Chemical compound O=C=NCC(C)(C)OC(=O)C=C WTKDTRXVTIKPCO-UHFFFAOYSA-N 0.000 description 1
- MAIIXYUYRNFKPL-UPHRSURJSA-N (z)-4-(2-hydroxyethoxy)-4-oxobut-2-enoic acid Chemical compound OCCOC(=O)\C=C/C(O)=O MAIIXYUYRNFKPL-UPHRSURJSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- ODKSRULWLOLNJQ-UHFFFAOYSA-N 1,2-diisocyanatocyclohexane Chemical compound O=C=NC1CCCCC1N=C=O ODKSRULWLOLNJQ-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-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
- QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 1
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- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
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- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
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- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
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- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
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- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000011326 mechanical measurement Methods 0.000 description 1
- 229940063559 methacrylic acid Drugs 0.000 description 1
- 229940086559 methyl benzoin Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 229930193351 phorone Natural products 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- 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
- C08F290/08—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 side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/148—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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Eyeglasses (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/638,949 US5194556A (en) | 1991-01-09 | 1991-01-09 | Rigid contact lenses with improved oxygen permeability |
| US638949 | 1991-01-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1008892A AU1008892A (en) | 1992-07-16 |
| AU654520B2 true AU654520B2 (en) | 1994-11-10 |
Family
ID=24562117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU10088/92A Ceased AU654520B2 (en) | 1991-01-09 | 1992-01-06 | Rigid contact lenses with improved oxygen permeability |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5194556A (enExample) |
| EP (1) | EP0494842B1 (enExample) |
| JP (2) | JP3322898B2 (enExample) |
| KR (1) | KR920014841A (enExample) |
| AT (1) | ATE165375T1 (enExample) |
| AU (1) | AU654520B2 (enExample) |
| CA (1) | CA2058896C (enExample) |
| DE (1) | DE69225151T2 (enExample) |
| DK (1) | DK0494842T3 (enExample) |
| ES (1) | ES2115660T3 (enExample) |
| GR (1) | GR3026729T3 (enExample) |
| IE (1) | IE920062A1 (enExample) |
| SG (1) | SG49603A1 (enExample) |
| TW (1) | TW222655B (enExample) |
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| US5194556A (en) * | 1991-01-09 | 1993-03-16 | Ciba-Geigy Corporation | Rigid contact lenses with improved oxygen permeability |
| JP3195662B2 (ja) * | 1992-08-24 | 2001-08-06 | 株式会社メニコン | 眼用レンズ材料 |
| JP2774233B2 (ja) * | 1992-08-26 | 1998-07-09 | 株式会社メニコン | 眼用レンズ材料 |
| US5310571A (en) * | 1992-09-01 | 1994-05-10 | Allergan, Inc. | Chemical treatment to improve oxygen permeability through and protein deposition on hydrophilic (soft) and rigid gas permeable (RGP) contact lenses |
| US5760100B1 (en) * | 1994-09-06 | 2000-11-14 | Ciba Vision Corp | Extended wear ophthalmic lens |
| US7468398B2 (en) * | 1994-09-06 | 2008-12-23 | Ciba Vision Corporation | Extended wear ophthalmic lens |
| JP3530287B2 (ja) * | 1995-10-24 | 2004-05-24 | 株式会社メニコン | 低含水性眼用レンズ用材料、それからなる低含水性眼用レンズ用成形体、ならびにそれからなる低含水性眼用レンズおよびその製法 |
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| AU7533696A (en) * | 1996-12-13 | 1998-06-18 | Ciba-Geigy Ag | New materials |
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| JP4438162B2 (ja) * | 2000-02-24 | 2010-03-24 | 東レ株式会社 | 眼用レンズ用ポリマーの製造法および眼用レンズ |
| AU2001278757B2 (en) * | 2001-08-17 | 2008-03-06 | Johnson & Johnson Vision Care, Inc. | Method for producing polymer for ophthalmic lens and ophthalmic lens |
| WO2003042265A1 (fr) * | 2001-11-13 | 2003-05-22 | Toray Industries, Inc. | Polymere et lentilles ophthalmologiques realisees a l'aide de ce polymere |
| FR2832717B1 (fr) * | 2001-11-26 | 2004-07-09 | Essilor Int | Composition polymerisable par voie radicalaire conduisant a des verres organiques resistants au choc |
| US7216975B2 (en) * | 2003-07-15 | 2007-05-15 | Shinn-Gwo Hong | Method for preparing the reactive tinting compound and the tinted contact lens |
| GB0327067D0 (en) * | 2003-11-21 | 2003-12-24 | Dow Corning | Polymeric products useful as oil repellents |
| US8153726B2 (en) | 2005-09-30 | 2012-04-10 | The Lagado Corporation | Highly oxygen permeable rigid contact lenses from polyacetylenes |
| JP5006061B2 (ja) | 2006-02-07 | 2012-08-22 | 日本合成化学工業株式会社 | 水溶性ポリビニルアルコール系樹脂製長繊維不織布 |
| US7601766B2 (en) * | 2006-06-30 | 2009-10-13 | Bausch & Lomb Incorporated | Carboxylic siloxanyl monomers with pendant polymerizable groups |
| CN101522792B (zh) * | 2006-10-02 | 2013-01-09 | 日立化成工业株式会社 | 密封用环氧树脂成形材料以及电子零件装置 |
| DE102007039501A1 (de) * | 2007-08-21 | 2009-02-26 | Evonik Röhm Gmbh | Neues polymerisierbares Isocyanat und Polymere, enthaltend dieses Isocyanat |
| US8440738B2 (en) * | 2008-07-09 | 2013-05-14 | Timothy Higgs | Silicone hydrogels and methods of manufacture |
| US7939579B1 (en) * | 2008-07-09 | 2011-05-10 | Contamac Limited | Hydrogels and methods of manufacture |
| NZ591769A (en) * | 2008-11-13 | 2012-06-29 | Novartis Ag | Polysiloxane copolymers with terminal hydrophilic polymer chains |
| NZ592674A (en) * | 2008-12-18 | 2012-08-31 | Novartis Ag | Method for making silicone hydrogel contact lenses |
| US8557940B2 (en) | 2010-07-30 | 2013-10-15 | Novartis Ag | Amphiphilic polysiloxane prepolymers and uses thereof |
| CN101928498B (zh) * | 2010-08-24 | 2014-04-23 | 中国电力科学研究院 | 一种氟硅改性丙烯酸树脂疏水防腐涂料 |
| WO2012047961A1 (en) | 2010-10-06 | 2012-04-12 | Novartis Ag | Polymerizable chain-extended polysiloxanes with pendant hydrophilic groups |
| WO2012047969A1 (en) | 2010-10-06 | 2012-04-12 | Novartis Ag | Water-processable silicone-containing prepolymers and uses thereof |
| WO2012047964A1 (en) | 2010-10-06 | 2012-04-12 | Novartis Ag | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
| CN103717632B (zh) * | 2011-07-19 | 2015-12-02 | 株式会社普利司通 | 光固化性树脂组合物、及使用其的湿区构件和功能性板 |
| US8937133B2 (en) | 2012-09-25 | 2015-01-20 | National Chiao Tung University | Dissoluble PDMS-modified p(HEMA-MAA) amphiphilic copolymer and method for fabricating the same |
| TWI535793B (zh) * | 2013-01-31 | 2016-06-01 | 明基材料股份有限公司 | 隱形眼鏡材料、隱形眼鏡的製造方法與由此方法所製造出之隱形眼鏡 |
| US9528869B2 (en) | 2014-12-16 | 2016-12-27 | Schlumberger Technology Corporation | Method of compensating for changes in water properties in a multiphase flow meter |
| US11035983B2 (en) * | 2016-09-26 | 2021-06-15 | Verily Life Sciences Llc | Cast-moldable, high refractive index, rigid, gas permeable polymer formulations for an accommodating contact lens |
| CN114026187B (zh) * | 2019-06-27 | 2023-03-10 | 3M创新有限公司 | 具有高折射率的金属-聚合物杂化材料 |
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-
1991
- 1991-01-09 US US07/638,949 patent/US5194556A/en not_active Expired - Lifetime
-
1992
- 1992-01-06 DK DK92810002T patent/DK0494842T3/da active
- 1992-01-06 EP EP92810002A patent/EP0494842B1/en not_active Expired - Lifetime
- 1992-01-06 AT AT92810002T patent/ATE165375T1/de not_active IP Right Cessation
- 1992-01-06 DE DE69225151T patent/DE69225151T2/de not_active Expired - Lifetime
- 1992-01-06 AU AU10088/92A patent/AU654520B2/en not_active Ceased
- 1992-01-06 SG SG1996000723A patent/SG49603A1/en unknown
- 1992-01-06 ES ES92810002T patent/ES2115660T3/es not_active Expired - Lifetime
- 1992-01-07 CA CA002058896A patent/CA2058896C/en not_active Expired - Fee Related
- 1992-01-08 IE IE006292A patent/IE920062A1/en not_active IP Right Cessation
- 1992-01-08 TW TW081100106A patent/TW222655B/zh active
- 1992-01-08 JP JP01834392A patent/JP3322898B2/ja not_active Expired - Fee Related
- 1992-01-08 KR KR1019920000113A patent/KR920014841A/ko not_active Abandoned
-
1998
- 1998-04-28 GR GR980400918T patent/GR3026729T3/el unknown
-
2002
- 2002-03-11 JP JP2002065116A patent/JP2002284828A/ja active Pending
Patent Citations (3)
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| US4486577A (en) * | 1982-10-12 | 1984-12-04 | Ciba-Geigy Corporation | Strong, silicone containing polymers with high oxygen permeability |
| US5023305A (en) * | 1986-09-30 | 1991-06-11 | Hoya Corporation | Oxygen-permeable hard contact lens material with excellent impact resistance |
| AU646033B2 (en) * | 1990-04-26 | 1994-02-03 | Novartis Ag | Unsaturated urea polysiloxanes |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1009064A1 (en) | 1999-05-21 |
| EP0494842A3 (en) | 1992-08-05 |
| AU1008892A (en) | 1992-07-16 |
| CA2058896C (en) | 2004-08-03 |
| SG49603A1 (en) | 2001-01-16 |
| DE69225151T2 (de) | 1998-10-22 |
| JP2002284828A (ja) | 2002-10-03 |
| CA2058896A1 (en) | 1992-07-10 |
| DK0494842T3 (da) | 1998-11-30 |
| DE69225151D1 (de) | 1998-05-28 |
| TW222655B (enExample) | 1994-04-21 |
| EP0494842A2 (en) | 1992-07-15 |
| ATE165375T1 (de) | 1998-05-15 |
| JPH05117349A (ja) | 1993-05-14 |
| JP3322898B2 (ja) | 2002-09-09 |
| EP0494842B1 (en) | 1998-04-22 |
| ES2115660T3 (es) | 1998-07-01 |
| IE920062A1 (en) | 1992-07-15 |
| GR3026729T3 (en) | 1998-07-31 |
| KR920014841A (ko) | 1992-08-25 |
| US5194556A (en) | 1993-03-16 |
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