CA1304366C - Monomeres et polymeres vinyliques absorbant les u.-v. et implants oculaires prepares a partir de ceux-ci - Google Patents

Monomeres et polymeres vinyliques absorbant les u.-v. et implants oculaires prepares a partir de ceux-ci

Info

Publication number: CA1304366C
Authority: CA; Canada
Prior art keywords: copolymer; ultraviolet light; light absorbing; homopolymer; monomer
Prior art date: 1987-10-15
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.): Expired - Lifetime

Application number

CA000580038A

Other languages

English (en)

Inventor

Ching-Wang Luo

Eugene P. Goldberg

Fu-Mian Li

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

University of Florida

Original Assignee

University of Florida

Priority date (The priority date 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 date listed.)

1987-10-15

Filing date

1988-10-13

Publication date

1992-06-30

1988-10-13 Application filed by University of Florida filed Critical University of Florida

1992-06-30 Application granted granted Critical

1992-06-30 Publication of CA1304366C publication Critical patent/CA1304366C/fr

2009-06-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000178 monomer Substances 0.000 title claims abstract description 56
229920000642 polymer Polymers 0.000 title claims description 17
239000007943 implant Substances 0.000 title claims description 12
229920002554 vinyl polymer Polymers 0.000 title description 9
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title description 6
229920001577 copolymer Polymers 0.000 claims abstract description 37
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
229920001519 homopolymer Polymers 0.000 claims abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000005157 alkyl carboxy group Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 17
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 16
229940102838 methylmethacrylate Drugs 0.000 claims description 13
239000000017 hydrogel Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 9
230000003287 optical effect Effects 0.000 claims description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 3
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical class CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 3
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical class CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
150000003926 acrylamides Chemical class 0.000 claims description 2
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims 1
UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical class C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 claims 1
UTNFQABGIDNKDO-UHFFFAOYSA-N 2-(hydroxymethylidene)butanoic acid Chemical class CCC(=CO)C(O)=O UTNFQABGIDNKDO-UHFFFAOYSA-N 0.000 claims 1
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical class OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
239000003000 extruded plastic Substances 0.000 claims 1
239000002991 molded plastic Substances 0.000 claims 1
239000002985 plastic film Substances 0.000 claims 1
229920006255 plastic film Polymers 0.000 claims 1
210000000695 crystalline len Anatomy 0.000 description 20
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 18
239000000463 material Substances 0.000 description 15
230000005540 biological transmission Effects 0.000 description 10
229920003229 poly(methyl methacrylate) Polymers 0.000 description 8
239000004926 polymethyl methacrylate Substances 0.000 description 8
238000007334 copolymerization reaction Methods 0.000 description 7
238000000034 method Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000006096 absorbing agent Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
UKDZROJJLPDLDO-UHFFFAOYSA-N 10h-pyrido[3,2-b][1,4]benzothiazine Chemical class C1=CN=C2NC3=CC=CC=C3SC2=C1 UKDZROJJLPDLDO-UHFFFAOYSA-N 0.000 description 5
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000005520 cutting process Methods 0.000 description 4
239000003999 initiator Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
JWGBOHJGWOPYCL-UHFFFAOYSA-N 1-(10H-phenothiazin-2-yl)ethanone Chemical compound C1=CC=C2NC3=CC(C(=O)C)=CC=C3SC2=C1 JWGBOHJGWOPYCL-UHFFFAOYSA-N 0.000 description 3
YATXLDXDEJIPPM-UHFFFAOYSA-N 2-methyl-1-pyrido[3,2-b][1,4]benzothiazin-10-ylprop-2-en-1-one Chemical compound C1=CN=C2N(C(=O)C(=C)C)C3=CC=CC=C3SC2=C1 YATXLDXDEJIPPM-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
-1 R3 is H Chemical group 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
238000013019 agitation Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
238000000465 moulding Methods 0.000 description 3
229950000688 phenothiazine Drugs 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000000411 transmission spectrum Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
JVFRDIXTLAPMGO-UHFFFAOYSA-N 1-pyrido[3,2-b][1,4]benzothiazin-10-ylprop-2-en-1-one Chemical compound C1=CN=C2N(C(=O)C=C)C3=CC=CC=C3SC2=C1 JVFRDIXTLAPMGO-UHFFFAOYSA-N 0.000 description 2
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
206010002945 Aphakia Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229920006243 acrylic copolymer Polymers 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
239000012965 benzophenone Substances 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
230000015556 catabolic process Effects 0.000 description 2
238000011109 contamination Methods 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000031700 light absorption Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229940063557 methacrylate Drugs 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
150000002990 phenothiazines Chemical class 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
238000005498 polishing Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000005855 radiation Effects 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
210000001525 retina Anatomy 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RZNGCTRCYDPVCV-UHFFFAOYSA-N (8-chloro-10h-phenothiazin-2-yl)-phenylmethanone Chemical compound C1=C2NC3=CC(Cl)=CC=C3SC2=CC=C1C(=O)C1=CC=CC=C1 RZNGCTRCYDPVCV-UHFFFAOYSA-N 0.000 description 1
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-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
KFZGLJSYQXZIGP-UHFFFAOYSA-N 2-chloro-10h-phenothiazine Chemical compound C1=CC=C2NC3=CC(Cl)=CC=C3SC2=C1 KFZGLJSYQXZIGP-UHFFFAOYSA-N 0.000 description 1
KDRNOBUWMVLVFH-UHFFFAOYSA-N 2-methyl-n-(2,2,6,6-tetramethylpiperidin-4-yl)prop-2-enamide Chemical compound CC(=C)C(=O)NC1CC(C)(C)NC(C)(C)C1 KDRNOBUWMVLVFH-UHFFFAOYSA-N 0.000 description 1
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
SLVZCEATCJMAEC-UHFFFAOYSA-N C=COC(=O)C=C.C=COC(=O)C=C Chemical class C=COC(=O)C=C.C=COC(=O)C=C SLVZCEATCJMAEC-UHFFFAOYSA-N 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
101000740112 Homo sapiens Membrane-associated transporter protein Proteins 0.000 description 1
102100037258 Membrane-associated transporter protein Human genes 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
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
238000012644 addition polymerization Methods 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
210000002159 anterior chamber Anatomy 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
230000001010 compromised effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000005284 excitation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
229920001480 hydrophilic copolymer Polymers 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002386 leaching Methods 0.000 description 1
230000007774 longterm Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920000120 polyethyl acrylate Polymers 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
239000007870 radical polymerization initiator Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
229940124543 ultraviolet light absorber Drugs 0.000 description 1
239000006097 ultraviolet radiation absorber Substances 0.000 description 1
238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1

Landscapes

Materials For Medical Uses (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000580038A 1987-10-15 1988-10-13 Monomeres et polymeres vinyliques absorbant les u.-v. et implants oculaires prepares a partir de ceux-ci Expired - Lifetime CA1304366C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US10869087A	1987-10-15	1987-10-15
US108,690		1987-10-15

Publications (1)

Publication Number	Publication Date
CA1304366C true CA1304366C (fr)	1992-06-30

Family

ID=22323551

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000580038A Expired - Lifetime CA1304366C (fr)	1987-10-15	1988-10-13	Monomeres et polymeres vinyliques absorbant les u.-v. et implants oculaires prepares a partir de ceux-ci

Country Status (1)

Country	Link
CA (1)	CA1304366C (fr)

1988
- 1988-10-13 CA CA000580038A patent/CA1304366C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1996-01-01	MKLA	Lapsed

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