DE60008076T2 - Verfahren zur Darstellung eines Latex mit photochromatischen Eigenschaften und dessen Anwendung insbesondere im ophthalmischen Bereich - Google Patents
Verfahren zur Darstellung eines Latex mit photochromatischen Eigenschaften und dessen Anwendung insbesondere im ophthalmischen Bereich Download PDFInfo
- Publication number
- DE60008076T2 DE60008076T2 DE60008076T DE60008076T DE60008076T2 DE 60008076 T2 DE60008076 T2 DE 60008076T2 DE 60008076 T DE60008076 T DE 60008076T DE 60008076 T DE60008076 T DE 60008076T DE 60008076 T2 DE60008076 T2 DE 60008076T2
- Authority
- DE
- Germany
- Prior art keywords
- latex
- photochromatic
- organic
- monomer
- composition
- 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.)
- Expired - Lifetime
Links
- 239000004816 latex Substances 0.000 title claims abstract description 59
- 229920000126 latex Polymers 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000178 monomer Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000003999 initiator Substances 0.000 claims description 25
- 239000000839 emulsion Substances 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000000576 coating method Methods 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 239000006117 anti-reflective coating Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 229920001519 homopolymer Polymers 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000002051 biphasic effect Effects 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000002861 polymer material Substances 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 1
- 239000011258 core-shell material Substances 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 239000010409 thin film Substances 0.000 abstract description 3
- 239000010408 film Substances 0.000 description 15
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 241000219739 Lens Species 0.000 description 10
- 239000010410 layer Substances 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- -1 silver halide Chemical class 0.000 description 8
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 7
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 230000000379 polymerizing effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003094 microcapsule Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000694 effects Effects 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- MBOUDGFDYRCXHO-UHFFFAOYSA-N 2-methylprop-2-enoic acid;phenol Chemical class CC(=C)C(O)=O.OC1=CC=CC=C1.OC1=CC=CC=C1 MBOUDGFDYRCXHO-UHFFFAOYSA-N 0.000 description 1
- WGZOKQDIGZFRNE-UHFFFAOYSA-N 2H-chromene 6-ethenyl-4,4,6-trimethyl-1-nitrocyclohexene Chemical compound O1CC=CC2=C1C=CC=C2.[N+](=O)([O-])C2=CCC(CC2(C=C)C)(C)C WGZOKQDIGZFRNE-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- TYBKOVLWQWMOCI-UHFFFAOYSA-N but-1-ene-1,3-diol Chemical compound CC(O)C=CO TYBKOVLWQWMOCI-UHFFFAOYSA-N 0.000 description 1
- OZCRKDNRAAKDAN-UHFFFAOYSA-N but-1-ene-1,4-diol Chemical compound O[CH][CH]CCO OZCRKDNRAAKDAN-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000008371 chromenes Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 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
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002966 varnish 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
- 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
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Eyeglasses (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Optical Filters (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9902437A FR2790264A1 (fr) | 1999-02-26 | 1999-02-26 | Procede de preparation d'un latex a proprietes photochromiques et ses applications, en particulier dans le domaine ophtalmique |
| FR9902437 | 1999-02-26 | ||
| PCT/FR2000/000397 WO2000050533A1 (fr) | 1999-02-26 | 2000-02-17 | Procede de preparation d'un latex a proprietes photochromiques et ses applications, en particulier dans le domaine ophtalmique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60008076D1 DE60008076D1 (de) | 2004-03-11 |
| DE60008076T2 true DE60008076T2 (de) | 2004-11-11 |
Family
ID=9542593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60008076T Expired - Lifetime DE60008076T2 (de) | 1999-02-26 | 2000-02-17 | Verfahren zur Darstellung eines Latex mit photochromatischen Eigenschaften und dessen Anwendung insbesondere im ophthalmischen Bereich |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7186359B2 (https=) |
| EP (1) | EP1161512B1 (https=) |
| JP (1) | JP4641621B2 (https=) |
| AT (1) | ATE258970T1 (https=) |
| AU (1) | AU762653B2 (https=) |
| BR (1) | BR0008529B1 (https=) |
| DE (1) | DE60008076T2 (https=) |
| ES (1) | ES2211508T3 (https=) |
| FR (1) | FR2790264A1 (https=) |
| WO (1) | WO2000050533A1 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2790264A1 (fr) * | 1999-02-26 | 2000-09-01 | Essilor Int | Procede de preparation d'un latex a proprietes photochromiques et ses applications, en particulier dans le domaine ophtalmique |
| FR2816950B1 (fr) * | 2000-11-17 | 2003-02-14 | Essilor Int | Procede d'obtention d'un latex photochromique |
| FR2819258B1 (fr) * | 2001-01-11 | 2003-04-11 | Essilor Int | Procede d'obtention d'un latex photochromique stabilise, latex obtenu et application a l'optique ophtalmique |
| FR2819800B1 (fr) * | 2001-01-25 | 2003-08-29 | Essilor Int | Procede d'incorporation d'un additif dans une couche mince formee sur un substrat et son application a l'optique ophtalmique |
| US6562466B2 (en) | 2001-07-02 | 2003-05-13 | Essilor International Compagnie Generale D'optique | Process for transferring a coating onto a surface of a lens blank |
| US8563212B2 (en) * | 2004-07-16 | 2013-10-22 | Transitions Optical, Inc. | Methods for producing photosensitive microparticles, non-aqueous dispersions thereof and articles prepared therewith |
| US8563213B2 (en) * | 2004-07-16 | 2013-10-22 | Transitions Optical, Inc. | Methods for producing photosensitive microparticles |
| US8153344B2 (en) | 2004-07-16 | 2012-04-10 | Ppg Industries Ohio, Inc. | Methods for producing photosensitive microparticles, aqueous compositions thereof and articles prepared therewith |
| US20080006368A9 (en) | 2005-02-01 | 2008-01-10 | Peiqi Jiang | Process for applying a coating onto a surface of a lens substrate |
| US20060219347A1 (en) | 2005-04-04 | 2006-10-05 | Essilor International Compagnie Generale D'optique | Process for transferring coatings onto a surface of a lens substrate with most precise optical quality |
| KR100875364B1 (ko) * | 2005-12-02 | 2008-12-22 | 주식회사 엘지화학 | 광변색성 나노입자의 제조방법 및 이로부터 제조되는광변색성 나노 입자 |
| US7892387B2 (en) | 2006-05-19 | 2011-02-22 | International Compagnie Generale d'Optique | Process and system for applying a coating onto a surface of a lens substrate |
| EP2147685B1 (en) | 2008-07-21 | 2011-09-28 | Essilor International (Compagnie Générale D'Optique) | Abrasion-resistant optical article and process for manufacturing thereof |
| US20100096602A1 (en) * | 2008-10-21 | 2010-04-22 | Herbert Mosse | System and method for improving adhesion and abrasion resistance using a front side transfer process to manufacture multi-coated photochromic optical lenses |
| US9132594B2 (en) | 2008-11-04 | 2015-09-15 | Essilor International (Compagnie Générale d'Optique) | Bi-layer adhesive for lens lamination |
| US8287953B2 (en) | 2009-02-09 | 2012-10-16 | Essilor International (Compagnie Generale D'optique) | Method for spin coating a surface of an optical article |
| JP5922024B2 (ja) * | 2009-10-27 | 2016-05-24 | エージェンシー フォー サイエンス， テクノロジー アンド リサーチ | 高速応答のフォトクロミックナノ構造コンタクトレンズ |
| JP5757954B2 (ja) | 2009-11-02 | 2015-08-05 | エシロル アンテルナショナル（コンパーニュ ジェネラル ドプテーク） | 積層レンズのための三層接着剤系及びその適用法 |
| ES2771099T3 (es) | 2012-05-22 | 2020-07-06 | Dsm Ip Assets Bv | Composición y proceso para producir un recubrimiento de óxido inorgánico poroso |
| FR2996930B1 (fr) | 2012-10-11 | 2017-11-24 | Essilor Int | Lentille ophtalmique photochromique |
| CA2930509A1 (en) * | 2013-11-22 | 2015-05-28 | Dsm Ip Assets B.V. | Process for making an anti-reflective coating composition and a porous coating made therefrom |
| ES2689126T3 (es) | 2014-01-31 | 2018-11-08 | Essilor International | Estructura de polarización que comprende un sistema adhesivo de glioxal y lente polarizada que la comprende |
| EP3164892B1 (en) | 2014-07-04 | 2018-08-29 | DSM IP Assets B.V. | Co-extruded backsheet for solar cell modules |
| US10017690B2 (en) * | 2015-05-28 | 2018-07-10 | Xerox Corporation | Photochromatic composition for 3D printing |
| ES2929943T3 (es) * | 2017-12-29 | 2022-12-05 | Essilor Int | Proceso de fabricación de una matriz polimérica absorbente de luz |
| JP2024037393A (ja) * | 2022-09-07 | 2024-03-19 | 三菱鉛筆株式会社 | フォトクロミック粒子水分散体及びこれを含有した水性インク組成物 |
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| JPS53111336A (en) * | 1977-03-11 | 1978-09-28 | Toray Ind Inc | Coating composition |
| FR2414071A1 (fr) * | 1978-01-05 | 1979-08-03 | Essilor Int | Materiau de polissage, notamment pour lentille ophtalmique en matiere organique |
| GB2104504B (en) * | 1981-07-16 | 1985-05-09 | English Clays Lovering Pochin | Stabilisation of photochromic fulgides and fulgimides |
| US4489108A (en) * | 1982-03-11 | 1984-12-18 | Ciba-Geigy Ag | Photochromic assembly and manufacture of this assembly |
| US4931220A (en) * | 1987-11-24 | 1990-06-05 | Ppg Industries, Inc. | Organic photochromic pigment particulates |
| EP0346484B1 (en) * | 1987-12-02 | 1995-08-16 | Japan Capsular Products, Inc. | Microencapsulated photochromic material, process for its preparation, and water-base ink composition prepared therefrom |
| JPH0220575A (ja) * | 1988-07-07 | 1990-01-24 | Toray Ind Inc | 水分散性フォトクロミックペイント組成物 |
| JP2723303B2 (ja) * | 1989-08-18 | 1998-03-09 | 株式会社トクヤマ | クロメン組成物 |
| JP2801347B2 (ja) * | 1990-03-02 | 1998-09-21 | 株式会社トクヤマ | フォトクロミック成形体 |
| US5066818A (en) * | 1990-03-07 | 1991-11-19 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
| US5238981A (en) * | 1992-02-24 | 1993-08-24 | Transitions Optical, Inc. | Photochromic naphthopyrans |
| GB2270321A (en) * | 1992-09-02 | 1994-03-09 | Matsui Shikiso Kagaku Kogyosho | A microencapsulated photochromic composition for textile printing paste use |
| FR2734827B1 (fr) * | 1995-05-31 | 1997-07-11 | Essilor Int | Compositions polymerisables a base de monomeres thio (meth)acrylates, polymeres a faible indice de jaune obtenus a partir de telles compositions et lentilles ophtalmiques correspondantes |
| JPH0931453A (ja) * | 1995-07-18 | 1997-02-04 | Fuji Photo Film Co Ltd | マイクロカプセルとそれを用いた要素 |
| RU2095836C1 (ru) * | 1995-07-20 | 1997-11-10 | Войсковая часть 33825 | Способ получения микрокапсул с органическим фотохромным соединением в полимерной матрице |
| JP3859260B2 (ja) * | 1996-04-09 | 2006-12-20 | 三菱化学株式会社 | 水性着色樹脂分散体、水性インク及びインクジェット用記録液 |
| JPH1025471A (ja) * | 1996-07-11 | 1998-01-27 | Fuji Photo Film Co Ltd | フォトクロミックな感光材料 |
| US5919404A (en) * | 1997-04-23 | 1999-07-06 | The Pilot Ink Co., Ltd. | Reversible thermochromic compositions |
| FR2790264A1 (fr) * | 1999-02-26 | 2000-09-01 | Essilor Int | Procede de preparation d'un latex a proprietes photochromiques et ses applications, en particulier dans le domaine ophtalmique |
| FR2816950B1 (fr) * | 2000-11-17 | 2003-02-14 | Essilor Int | Procede d'obtention d'un latex photochromique |
| FR2819258B1 (fr) * | 2001-01-11 | 2003-04-11 | Essilor Int | Procede d'obtention d'un latex photochromique stabilise, latex obtenu et application a l'optique ophtalmique |
-
1999
- 1999-02-26 FR FR9902437A patent/FR2790264A1/fr active Pending
-
2000
- 2000-02-17 JP JP2000601098A patent/JP4641621B2/ja not_active Expired - Lifetime
- 2000-02-17 EP EP00906415A patent/EP1161512B1/fr not_active Expired - Lifetime
- 2000-02-17 ES ES00906415T patent/ES2211508T3/es not_active Expired - Lifetime
- 2000-02-17 BR BRPI0008529-4A patent/BR0008529B1/pt not_active IP Right Cessation
- 2000-02-17 AU AU28097/00A patent/AU762653B2/en not_active Ceased
- 2000-02-17 WO PCT/FR2000/000397 patent/WO2000050533A1/fr not_active Ceased
- 2000-02-17 DE DE60008076T patent/DE60008076T2/de not_active Expired - Lifetime
- 2000-02-17 AT AT00906415T patent/ATE258970T1/de not_active IP Right Cessation
-
2001
- 2001-08-24 US US09/939,151 patent/US7186359B2/en not_active Expired - Lifetime
-
2007
- 2007-01-19 US US11/625,087 patent/US20070115426A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20020128339A1 (en) | 2002-09-12 |
| BR0008529B1 (pt) | 2010-06-15 |
| JP4641621B2 (ja) | 2011-03-02 |
| AU762653B2 (en) | 2003-07-03 |
| ES2211508T3 (es) | 2004-07-16 |
| ATE258970T1 (de) | 2004-02-15 |
| BR0008529A (pt) | 2001-11-06 |
| EP1161512A1 (fr) | 2001-12-12 |
| FR2790264A1 (fr) | 2000-09-01 |
| EP1161512B1 (fr) | 2004-02-04 |
| WO2000050533A1 (fr) | 2000-08-31 |
| DE60008076D1 (de) | 2004-03-11 |
| US20070115426A1 (en) | 2007-05-24 |
| US7186359B2 (en) | 2007-03-06 |
| AU2809700A (en) | 2000-09-14 |
| JP2002537473A (ja) | 2002-11-05 |
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