CA2261839A1 - Method and composition for incorporating radiation-absorbing agents into polymers - Google Patents
Method and composition for incorporating radiation-absorbing agents into polymers Download PDFInfo
- Publication number
- CA2261839A1 CA2261839A1 CA002261839A CA2261839A CA2261839A1 CA 2261839 A1 CA2261839 A1 CA 2261839A1 CA 002261839 A CA002261839 A CA 002261839A CA 2261839 A CA2261839 A CA 2261839A CA 2261839 A1 CA2261839 A1 CA 2261839A1
- Authority
- CA
- Canada
- Prior art keywords
- dye
- polymeric
- precursor
- crosslinkable
- polymeric dye
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 122
- 239000006096 absorbing agent Substances 0.000 title claims abstract description 37
- 229920000642 polymer Polymers 0.000 title claims description 149
- 239000000203 mixture Substances 0.000 title claims description 69
- 239000000975 dye Substances 0.000 claims abstract description 261
- 239000000463 material Substances 0.000 claims abstract description 101
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 57
- 238000004132 cross linking Methods 0.000 claims abstract description 41
- -1 poly(vinyl alcohol) Polymers 0.000 claims abstract description 35
- 238000000605 extraction Methods 0.000 claims abstract description 22
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 17
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 10
- 239000002243 precursor Substances 0.000 claims description 195
- 239000000243 solution Substances 0.000 claims description 88
- 239000000985 reactive dye Substances 0.000 claims description 52
- 238000000746 purification Methods 0.000 claims description 25
- 238000002156 mixing Methods 0.000 claims description 24
- 230000005855 radiation Effects 0.000 claims description 24
- 239000007864 aqueous solution Substances 0.000 claims description 21
- 238000000465 moulding Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 10
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- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 4
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- 239000003431 cross linking reagent Substances 0.000 claims description 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- 239000012266 salt solution Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
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- 229920001577 copolymer Polymers 0.000 description 4
- 230000001976 improved effect Effects 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229920003169 water-soluble polymer Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
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- 125000004956 cyclohexylene group Chemical group 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
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- 238000009472 formulation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229920006158 high molecular weight polymer Polymers 0.000 description 3
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- 150000002431 hydrogen Chemical class 0.000 description 3
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- KUIXZSYWBHSYCN-UHFFFAOYSA-L remazol brilliant blue r Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC(S(=O)(=O)CCOS([O-])(=O)=O)=C1 KUIXZSYWBHSYCN-UHFFFAOYSA-L 0.000 description 3
- HFIYIRIMGZMCPC-YOLJWEMLSA-J remazole black-GR Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(\N=N\C=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-YOLJWEMLSA-J 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- MGARLISKINLYPI-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)-2-methylprop-2-enamide Chemical compound COC(OC)CNC(=O)C(C)=C MGARLISKINLYPI-UHFFFAOYSA-N 0.000 description 2
- SZKQVAUBISBCLC-UHFFFAOYSA-N nitroperoxysulfonylformic acid Chemical compound [N+](=O)([O-])OOS(=O)(=O)C(=O)O SZKQVAUBISBCLC-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
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- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- ANOULJGZTVOIFB-UHFFFAOYSA-M sodium;1-amino-4-(3-ethenylsulfonylanilino)-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC(S(=O)(=O)C=C)=C1 ANOULJGZTVOIFB-UHFFFAOYSA-M 0.000 description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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- 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
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- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
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- FAPCFNWEPHTUQK-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1[O-] FAPCFNWEPHTUQK-UHFFFAOYSA-N 0.000 description 1
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- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-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
- 125000004974 2-butenyl group Chemical group C(C=CC)* 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
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- 125000005647 linker group Chemical group 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 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 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- WXQMFIJLJLLQIS-UHFFFAOYSA-N reactive blue 21 Chemical compound [Cu+2].C1=CC(S(=O)(=O)CCO)=CC=C1NS(=O)(=O)C1=CC=C2C([N-]3)=NC(C=4C5=CC=C(C=4)S(O)(=O)=O)=NC5=NC(C=4C5=CC=C(C=4)S(O)(=O)=O)=NC5=NC([N-]4)=C(C=C(C=C5)S(O)(=O)=O)C5=C4N=C3C2=C1 WXQMFIJLJLLQIS-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000010019 resist printing Methods 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 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
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-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
- 239000011343 solid material Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- ASTWEMOBIXQPPV-UHFFFAOYSA-K trisodium;phosphate;dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[O-]P([O-])([O-])=O ASTWEMOBIXQPPV-UHFFFAOYSA-K 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/937—Utility as body contact e.g. implant, contact lens or I.U.D.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Eyeglasses (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
- Polymerisation Methods In General (AREA)
- Surface Treatment Of Optical Elements (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69115796A | 1996-08-01 | 1996-08-01 | |
| US08/691,157 | 1996-08-01 | ||
| PCT/EP1997/004174 WO1998005690A1 (en) | 1996-08-01 | 1997-07-31 | Method and composition for incorporating radiation-absorbing agents into polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2261839A1 true CA2261839A1 (en) | 1998-02-12 |
Family
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Family Applications (1)
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|---|---|---|---|
| CA002261839A Abandoned CA2261839A1 (en) | 1996-08-01 | 1997-07-31 | Method and composition for incorporating radiation-absorbing agents into polymers |
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| Country | Link |
|---|---|
| US (1) | US6162844A (enExample) |
| EP (1) | EP0915914B1 (enExample) |
| JP (1) | JP2000515085A (enExample) |
| KR (1) | KR20000029695A (enExample) |
| CN (1) | CN1228788A (enExample) |
| AR (1) | AR008108A1 (enExample) |
| AT (1) | ATE263192T1 (enExample) |
| AU (1) | AU4012997A (enExample) |
| BR (1) | BR9711106A (enExample) |
| CA (1) | CA2261839A1 (enExample) |
| DE (1) | DE69728402T2 (enExample) |
| ID (1) | ID17749A (enExample) |
| IL (1) | IL128282A0 (enExample) |
| NO (1) | NO990441L (enExample) |
| WO (1) | WO1998005690A1 (enExample) |
| ZA (1) | ZA976812B (enExample) |
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| AR013444A1 (es) * | 1997-08-28 | 2000-12-27 | Novartis Ag | Metodo para incorporar agentes absorbentes de radiacion en polimeros y articulo |
| CA2307634C (en) * | 1997-11-14 | 2008-02-05 | Novartis Ag | Methods and compositions for manufacturing tinted ophthalmic lenses |
| US6149692A (en) * | 1998-08-27 | 2000-11-21 | Novartis Ag | Method and composition for incorporating radiation-absorbing agents into polymers |
| US6510005B1 (en) * | 1998-10-27 | 2003-01-21 | Irving S. Goldstein | Filter for illusion apparatus |
| US6149842A (en) * | 1998-11-12 | 2000-11-21 | Novartis Ag | Methods and compositions for manufacturing tinted ophthalmic lenses |
| ATE373682T1 (de) | 2000-03-13 | 2007-10-15 | Biocure Inc | Embolische zusammensetzungen |
| CA2402774C (en) * | 2000-03-13 | 2011-09-06 | Biocure, Inc. | Microsphere hydrogel biomedical articles |
| CA2401865C (en) * | 2000-03-24 | 2010-01-12 | Novartis Ag | Crosslinkable or polymerizable prepolymers |
| US6579096B2 (en) * | 2000-08-08 | 2003-06-17 | Paul C. Chiu | Method and system for selectively staining dental composite resin |
| US6774178B2 (en) | 2001-01-05 | 2004-08-10 | Novartis Ag | Tinted, high Dk ophthalmic molding and a method for making same |
| TWI261057B (en) * | 2001-03-07 | 2006-09-01 | Novartis Ag | Process for the manufacture of moldings |
| US7879267B2 (en) * | 2001-08-02 | 2011-02-01 | J&J Vision Care, Inc. | Method for coating articles by mold transfer |
| US20030141490A1 (en) * | 2001-12-21 | 2003-07-31 | Walters Robert W. | Photochromic polymer compositions and articles thereof |
| CN100349935C (zh) * | 2002-02-15 | 2007-11-21 | Zms有限责任公司 | 用于生物医学应用的聚合方法和材料 |
| JP4751067B2 (ja) * | 2002-08-14 | 2011-08-17 | ノバルティス アーゲー | 放射線硬化性プレポリマー |
| US20050085585A1 (en) | 2002-10-23 | 2005-04-21 | Quinn Michael H. | Polymerizable materials |
| US7288578B2 (en) * | 2002-11-01 | 2007-10-30 | Novartis Ag | Biocompatible inks, preparation, and uses thereof |
| US7216975B2 (en) * | 2003-07-15 | 2007-05-15 | Shinn-Gwo Hong | Method for preparing the reactive tinting compound and the tinted contact lens |
| BRPI0509338B1 (pt) * | 2004-04-30 | 2017-10-17 | Abbott Medical Optics Inc. | Detached devices having a highly selective violet light transmitter and related methods |
| ATE489058T1 (de) * | 2004-06-29 | 2010-12-15 | Inc Biocure | Bandscheiben-nucleus-pulposus-implantat |
| US8030369B2 (en) * | 2004-10-13 | 2011-10-04 | Novartis Ag | Contact lenses with improved wearing comfort |
| US8899547B2 (en) | 2004-11-18 | 2014-12-02 | Qspex Technologies, Inc. | Molds and method of using the same for optical lenses |
| US20070149641A1 (en) * | 2005-12-28 | 2007-06-28 | Goupil Dennis W | Injectable bone cement |
| RU2555704C2 (ru) | 2009-09-15 | 2015-07-10 | Новартис Аг | Преполимеры, применимые для изготовления поглощающих ультрафиолетовое излучение контактных линз |
| TWI573818B (zh) | 2010-07-30 | 2017-03-11 | 諾華公司 | 兩親性聚矽氧烷預聚物及其用途 |
| US8993651B2 (en) | 2010-10-06 | 2015-03-31 | Novartis Ag | Polymerizable chain-extended polysiloxanes with pendant hydrophilic groups |
| US8835525B2 (en) | 2010-10-06 | 2014-09-16 | Novartis Ag | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
| KR101565220B1 (ko) | 2010-10-06 | 2015-11-02 | 노파르티스 아게 | 수-가공성 실리콘-함유 예비중합체 및 그의 용도 |
| US9042019B2 (en) | 2011-04-15 | 2015-05-26 | Qspex Technologies, Inc. | Anti-reflective lenses and methods for manufacturing the same |
| US9335443B2 (en) | 2011-04-15 | 2016-05-10 | Qspex Technologies, Inc. | Anti-reflective lenses and methods for manufacturing the same |
| JP6580788B2 (ja) * | 2015-12-02 | 2019-09-25 | ノバルティス アーゲー | 水溶性ｕｖ吸収化合物およびその使用 |
| EP3788084A1 (en) | 2018-05-01 | 2021-03-10 | Bausch & Lomb Incorporated | Ophthalmic devices containing uv blocker and methods for their preparation |
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| US4157892A (en) * | 1973-02-21 | 1979-06-12 | Toyo Contact Lens Company, Limited | Method of coloring water-absorbable plastics and colored water-absorbable plastics |
| US4252421A (en) * | 1978-11-09 | 1981-02-24 | John D. McCarry | Contact lenses with a colored central area |
| US4559059A (en) * | 1981-08-12 | 1985-12-17 | Ciba-Geigy Corporation | Tinted contact lenses and a method for their preparation |
| PT75373B (en) * | 1981-08-12 | 1986-06-18 | Agripat Sa | Process for the preparation of tinted contact lenses |
| US4468229A (en) * | 1981-08-12 | 1984-08-28 | Ciba-Geigy Corporation | Tinted contact lenses and a method for their preparation with reactive dyes |
| US4553975A (en) * | 1981-08-12 | 1985-11-19 | Ciba Geigy Corporation | Tinted contact lenses and a method for their preparation |
| US4891046A (en) * | 1984-03-15 | 1990-01-02 | Coopervision, Inc. | Tinted contact lens and method for preparation with dichlorotriazine reactive dye |
| US4963160A (en) * | 1989-03-14 | 1990-10-16 | Ciba-Geigy Corporation | Reactive uv absorbing compositions and method of preparing lenses therefrom |
| US4929250A (en) * | 1989-03-14 | 1990-05-29 | Ciba-Geigy Corporation | Ultraviolet absorbing lenses and method of making the same |
| US5272212A (en) * | 1990-09-26 | 1993-12-21 | Nippon Zeon Co., Ltd. | Colored spherical fine particles, process for production thereof and applications thereof |
| CH680216A5 (enExample) * | 1990-10-23 | 1992-07-15 | Erwin Sen Hunziker | |
| JPH04293010A (ja) * | 1991-03-22 | 1992-10-16 | Seiko Epson Corp | 着色ソフトコンタクトレンズの製造方法 |
| US5292350A (en) * | 1992-04-24 | 1994-03-08 | Vistakon, Inc. | Method for preparing tinted contact lens |
| US5260716A (en) * | 1992-06-29 | 1993-11-09 | Eastman Kodak Company | Apparatus and method for thermal printing wherein donor slack is controlled by a capstan roller |
| NZ248969A (en) * | 1992-10-26 | 1995-08-28 | Johnson & Johnson Vision Prod | Tinted contact lens; method of preparation using reactive monomer-halotriazine dye adjunct |
| US5321112A (en) * | 1992-12-22 | 1994-06-14 | Minnesota Mining And Manufacturing Company | Copolymerizable ultraviolet radiation absorbing compounds and polymers made therewith |
| US5362812A (en) * | 1993-04-23 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Reactive polymeric dyes |
| TW272976B (enExample) * | 1993-08-06 | 1996-03-21 | Ciba Geigy Ag | |
| JPH07134272A (ja) * | 1993-11-08 | 1995-05-23 | Seiko Epson Corp | 着色ソフトコンタクトレンズの製造方法 |
| US5480927A (en) * | 1994-05-20 | 1996-01-02 | Ciba Geigy Corporation | Method of increasing the concentration of radiation-absorbing agents in optical and ophthalmic lenses |
| TW425410B (en) * | 1995-02-03 | 2001-03-11 | Novartis Ag | Preparation of the crosslinked tinted polymers and their moldings |
| JP3980667B2 (ja) * | 1995-07-07 | 2007-09-26 | 株式会社トーメー | 高分子染料およびその製法、ならびに該高分子染料を用いてなる着色コンタクトレンズおよびその製法 |
-
1997
- 1997-07-30 AR ARP970103436A patent/AR008108A1/es unknown
- 1997-07-31 WO PCT/EP1997/004174 patent/WO1998005690A1/en not_active Ceased
- 1997-07-31 JP JP10507589A patent/JP2000515085A/ja not_active Ceased
- 1997-07-31 ZA ZA9706812A patent/ZA976812B/xx unknown
- 1997-07-31 EP EP97937535A patent/EP0915914B1/en not_active Expired - Lifetime
- 1997-07-31 ID IDP972654A patent/ID17749A/id unknown
- 1997-07-31 AT AT97937535T patent/ATE263192T1/de not_active IP Right Cessation
- 1997-07-31 CN CN97197540A patent/CN1228788A/zh active Pending
- 1997-07-31 AU AU40129/97A patent/AU4012997A/en not_active Abandoned
- 1997-07-31 IL IL12828297A patent/IL128282A0/xx unknown
- 1997-07-31 KR KR1019997000774A patent/KR20000029695A/ko not_active Withdrawn
- 1997-07-31 BR BR9711106A patent/BR9711106A/pt unknown
- 1997-07-31 DE DE69728402T patent/DE69728402T2/de not_active Expired - Lifetime
- 1997-07-31 CA CA002261839A patent/CA2261839A1/en not_active Abandoned
-
1999
- 1999-01-29 NO NO990441A patent/NO990441L/no not_active Application Discontinuation
- 1999-12-22 US US09/469,680 patent/US6162844A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0915914B1 (en) | 2004-03-31 |
| ATE263192T1 (de) | 2004-04-15 |
| NO990441D0 (no) | 1999-01-29 |
| WO1998005690A1 (en) | 1998-02-12 |
| KR20000029695A (ko) | 2000-05-25 |
| BR9711106A (pt) | 1999-08-17 |
| JP2000515085A (ja) | 2000-11-14 |
| ID17749A (id) | 1998-01-22 |
| CN1228788A (zh) | 1999-09-15 |
| US6162844A (en) | 2000-12-19 |
| AR008108A1 (es) | 1999-12-09 |
| ZA976812B (en) | 1998-03-03 |
| EP0915914A1 (en) | 1999-05-19 |
| DE69728402T2 (de) | 2005-02-24 |
| IL128282A0 (en) | 1999-11-30 |
| AU4012997A (en) | 1998-02-25 |
| DE69728402D1 (de) | 2004-05-06 |
| NO990441L (no) | 1999-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |