FR2790264A1 - Procede de preparation d'un latex a proprietes photochromiques et ses applications, en particulier dans le domaine ophtalmique - Google Patents
Procede de preparation d'un latex a proprietes photochromiques et ses applications, en particulier dans le domaine ophtalmique Download PDFInfo
- Publication number
- FR2790264A1 FR2790264A1 FR9902437A FR9902437A FR2790264A1 FR 2790264 A1 FR2790264 A1 FR 2790264A1 FR 9902437 A FR9902437 A FR 9902437A FR 9902437 A FR9902437 A FR 9902437A FR 2790264 A1 FR2790264 A1 FR 2790264A1
- Authority
- FR
- France
- Prior art keywords
- latex
- photochromic
- composition
- organic
- monomer
- 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.)
- Pending
Links
- 239000004816 latex Substances 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 14
- 229920000126 latex Polymers 0.000 claims abstract description 53
- 239000000178 monomer Substances 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000000839 emulsion Substances 0.000 claims abstract description 22
- 239000003999 initiator Substances 0.000 claims abstract description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 20
- 238000000576 coating method Methods 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 14
- 239000011248 coating agent Substances 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 238000005299 abrasion Methods 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 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 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 3
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 230000002051 biphasic effect Effects 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000002861 polymer material Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 238000010526 radical polymerization reaction Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 abstract description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 14
- 239000010408 film Substances 0.000 description 14
- -1 silver halides Chemical class 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000000049 pigment Substances 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 7
- 239000010410 layer Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000011368 organic material Substances 0.000 description 5
- 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 description 4
- 238000005266 casting Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003094 microcapsule Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 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
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- PUFAFJLYWMNNEC-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCCOCCO PUFAFJLYWMNNEC-UHFFFAOYSA-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- WKYMAEGRRCJZRP-UHFFFAOYSA-N 3-(2-fluorophenyl)-8-methoxy-3-(4-methoxyphenyl)benzo[f]chromene Chemical compound C1=CC(OC)=CC=C1C1(C=2C(=CC=CC=2)F)C=CC2=C3C=CC(OC)=CC3=CC=C2O1 WKYMAEGRRCJZRP-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000014653 Carica parviflora Nutrition 0.000 description 1
- 241000243321 Cnidaria Species 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
- 239000004972 Polyurethane varnish Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 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
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 239000000872 buffer 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008371 chromenes Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 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
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution 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
- CXPOFJRHCFPDRI-UHFFFAOYSA-N dodecylbenzene;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1 CXPOFJRHCFPDRI-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910001448 ferrous ion Inorganic materials 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000001659 ion-beam spectroscopy Methods 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 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
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol 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
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- VPMTUQQBSUTFJT-UHFFFAOYSA-N propan-2-amine;dihydrochloride Chemical compound Cl.Cl.CC(C)N VPMTUQQBSUTFJT-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
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Optical Filters (AREA)
Priority Applications (13)
| 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 |
| JP2000601098A JP4641621B2 (ja) | 1999-02-26 | 2000-02-17 | フォトクロミック特性を有するラテックスの調製方法、および得られたラテックスの利用、特に眼科学の分野での利用 |
| DE60008076T DE60008076T2 (de) | 1999-02-26 | 2000-02-17 | Verfahren zur Darstellung eines Latex mit photochromatischen Eigenschaften und dessen Anwendung insbesondere im ophthalmischen Bereich |
| ES00906415T ES2211508T3 (es) | 1999-02-26 | 2000-02-17 | Procedimiento de preparacion de un laltex con propiedades fotocromicas y sus aplicaciones, en particular en el campo oftalmico. |
| PCT/FR2000/000398 WO2000050929A1 (fr) | 1999-02-26 | 2000-02-17 | Utilisation de copolyester statistique pour ameliorer la resistance aux chocs d'une lentille ophtalmique et lentille obtenue |
| AU28098/00A AU2809800A (en) | 1999-02-26 | 2000-02-17 | Use of random copolyester for enhancing impact resistance of an ophthalmic lens and resulting lens |
| BRPI0008529-4A BR0008529B1 (pt) | 1999-02-26 | 2000-02-17 | processo de preparação de um látex com propriedades fotocrÈmicas, látex com propriedades fotocrÈmicas, e, substrato revestido de uma pelìcula. |
| EP00906415A EP1161512B1 (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 |
| 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 |
| AU28097/00A AU762653B2 (en) | 1999-02-26 | 2000-02-17 | Method for preparing a latex with photochromic properties and uses thereof, particularly in ophthalmology |
| AT00906415T ATE258970T1 (de) | 1999-02-26 | 2000-02-17 | Verfahren zur herstellung von einem photochromen latex und dessen verwendung, insbesondere für ophthalmische anwendung |
| US09/939,151 US7186359B2 (en) | 1999-02-26 | 2001-08-24 | Method for preparing a latex with photochromic properties and uses thereof, particularly in ophthalmology |
| US11/625,087 US20070115426A1 (en) | 1999-02-26 | 2007-01-19 | Method for preparing a latex with photochromic properties and uses thereof, particularly in ophthalmology |
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2790264A1 true FR2790264A1 (fr) | 2000-09-01 |
Family
ID=9542593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9902437A Pending 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 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7186359B2 (enExample) |
| EP (1) | EP1161512B1 (enExample) |
| JP (1) | JP4641621B2 (enExample) |
| AT (1) | ATE258970T1 (enExample) |
| AU (1) | AU762653B2 (enExample) |
| BR (1) | BR0008529B1 (enExample) |
| DE (1) | DE60008076T2 (enExample) |
| ES (1) | ES2211508T3 (enExample) |
| FR (1) | FR2790264A1 (enExample) |
| WO (1) | WO2000050533A1 (enExample) |
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| WO2002040548A1 (fr) * | 2000-11-17 | 2002-05-23 | Essilor International Compagnie Generale D'optique | Procede d'obtention d'un latex photochromique |
| FR2819258A1 (fr) * | 2001-01-11 | 2002-07-12 | Essilor Int | Procede d'obtention d'un latex photochromique stabilise, latex obtenu et application a l'optique ophtalmique |
| WO2015075229A1 (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 |
| US10665742B2 (en) | 2014-07-04 | 2020-05-26 | Dsm Ip Assets B.V. | Co-extruded backsheet for solar cell modules |
| US11400430B2 (en) | 2012-05-22 | 2022-08-02 | Covestro (Netherlands) B.V. | Hybrid organic-inorganic nano-particles |
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| 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 |
| 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 |
| US8563213B2 (en) * | 2004-07-16 | 2013-10-22 | Transitions Optical, Inc. | Methods for producing photosensitive microparticles |
| US8563212B2 (en) * | 2004-07-16 | 2013-10-22 | Transitions Optical, Inc. | Methods for producing photosensitive microparticles, non-aqueous dispersions thereof and articles prepared therewith |
| 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 |
| JP2007154198A (ja) * | 2005-12-02 | 2007-06-21 | Lg Chem Ltd | フォトクロミックナノ粒子の製法及び該製法により調製されるフォトクロミックナノ粒子 |
| 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 |
| ATE526042T1 (de) | 2008-07-21 | 2011-10-15 | Essilor Int | Abriebfester optischer artikel und herstellungsverfahren dafür |
| 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 |
| US20120309761A1 (en) * | 2009-10-27 | 2012-12-06 | Agency For Science, Technology And Research | Fast-response photochromic nanostructured contact lenses |
| CN102639315B (zh) | 2009-11-02 | 2016-01-27 | 埃西勒国际通用光学公司 | 用于叠层镜片的三层粘合剂体系及其施加方法 |
| FR2996930B1 (fr) | 2012-10-11 | 2017-11-24 | Essilor Int | Lentille ophtalmique photochromique |
| 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 |
| 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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| EP0346484A1 (en) * | 1987-12-02 | 1989-12-20 | Japan Capsular Products, Inc. | Microencapsulated photochromic material, process for its preparation, and water-base ink composition prepared therefrom |
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| EP0873881A1 (en) * | 1997-04-23 | 1998-10-28 | The Pilot Ink CO., Ltd. | Reversible thermochromic compositions |
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- 2000-02-17 DE DE60008076T patent/DE60008076T2/de not_active Expired - Lifetime
- 2000-02-17 WO PCT/FR2000/000397 patent/WO2000050533A1/fr not_active Ceased
- 2000-02-17 AU AU28097/00A patent/AU762653B2/en not_active Ceased
- 2000-02-17 ES ES00906415T patent/ES2211508T3/es not_active Expired - Lifetime
- 2000-02-17 EP EP00906415A patent/EP1161512B1/fr not_active Expired - Lifetime
- 2000-02-17 BR BRPI0008529-4A patent/BR0008529B1/pt not_active IP Right Cessation
- 2000-02-17 AT AT00906415T patent/ATE258970T1/de not_active IP Right Cessation
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2001
- 2001-08-24 US US09/939,151 patent/US7186359B2/en not_active Expired - Lifetime
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6770710B2 (en) | 2000-11-17 | 2004-08-03 | Essilor International Compagnie Generale D'optique | Process for obtaining a photochromic latex |
| FR2816950A1 (fr) * | 2000-11-17 | 2002-05-24 | Essilor Int | Procede d'obtention d'un latex photochromique |
| WO2002040548A1 (fr) * | 2000-11-17 | 2002-05-23 | Essilor International Compagnie Generale D'optique | Procede d'obtention d'un latex photochromique |
| AU2002229884B2 (en) * | 2001-01-11 | 2005-11-24 | Essilor International | Method for obtaining a stabilised photochromic latex, latex obtained and use in ophthalmic optics |
| US6740699B2 (en) | 2001-01-11 | 2004-05-25 | Essilor International Compagnie Generale D'optique | Method for obtaining a stabilized photochromic latex, latex obtained, and application to ophthalmic optics |
| WO2002055564A1 (fr) * | 2001-01-11 | 2002-07-18 | Essilor International Compagnie Generale D'optique | Procede d'obtention d'un latex photochromique stabilise, latex obtenu et application a l'optique ophtalmique |
| FR2819258A1 (fr) * | 2001-01-11 | 2002-07-12 | Essilor Int | Procede d'obtention d'un latex photochromique stabilise, latex obtenu et application a l'optique ophtalmique |
| AU2002229884B8 (en) * | 2001-01-11 | 2005-12-08 | Essilor International | Method for obtaining a stabilised photochromic latex, latex obtained and use in ophthalmic optics |
| US11400430B2 (en) | 2012-05-22 | 2022-08-02 | Covestro (Netherlands) B.V. | Hybrid organic-inorganic nano-particles |
| WO2015075229A1 (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 |
| AU2014351831B2 (en) * | 2013-11-22 | 2018-02-01 | Dsm Ip Assets B.V. | Process for making an anti-reflective coating composition and a porous coating made therefrom |
| EP3401369A1 (en) * | 2013-11-22 | 2018-11-14 | DSM IP Assets B.V. | Process for making an anti-reflective coating composition and a porous coating made therefrom |
| US10302819B2 (en) | 2013-11-22 | 2019-05-28 | Dsm Ip Assets B.V. | Process for making an anti-reflective coating composition and a porous coating made therefrom |
| US11009628B2 (en) | 2013-11-22 | 2021-05-18 | Dsm Ip Assets B.V. | Process for making an anti-reflective coating composition and a porous coating made therefrom |
| US10665742B2 (en) | 2014-07-04 | 2020-05-26 | Dsm Ip Assets B.V. | Co-extruded backsheet for solar cell modules |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1161512B1 (fr) | 2004-02-04 |
| EP1161512A1 (fr) | 2001-12-12 |
| ATE258970T1 (de) | 2004-02-15 |
| DE60008076T2 (de) | 2004-11-11 |
| US20070115426A1 (en) | 2007-05-24 |
| ES2211508T3 (es) | 2004-07-16 |
| JP2002537473A (ja) | 2002-11-05 |
| BR0008529B1 (pt) | 2010-06-15 |
| US20020128339A1 (en) | 2002-09-12 |
| BR0008529A (pt) | 2001-11-06 |
| AU2809700A (en) | 2000-09-14 |
| WO2000050533A1 (fr) | 2000-08-31 |
| US7186359B2 (en) | 2007-03-06 |
| JP4641621B2 (ja) | 2011-03-02 |
| AU762653B2 (en) | 2003-07-03 |
| DE60008076D1 (de) | 2004-03-11 |
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