DE3607759A1 - Photochromer gegenstand aus kunststoff und verfahren zu seiner herstellung - Google Patents
Photochromer gegenstand aus kunststoff und verfahren zu seiner herstellungInfo
- Publication number
- DE3607759A1 DE3607759A1 DE19863607759 DE3607759A DE3607759A1 DE 3607759 A1 DE3607759 A1 DE 3607759A1 DE 19863607759 DE19863607759 DE 19863607759 DE 3607759 A DE3607759 A DE 3607759A DE 3607759 A1 DE3607759 A1 DE 3607759A1
- Authority
- DE
- Germany
- Prior art keywords
- photochromic
- film
- spiro
- indoline
- plastic
- 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.)
- Granted
Links
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- 239000002904 solvent Substances 0.000 claims description 21
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 18
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- 238000010438 heat treatment Methods 0.000 claims description 13
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 10
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- 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 claims description 8
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- ITPCCQOGYMDBHK-UHFFFAOYSA-N 3h-benzo[f][1,2]benzoxazine;2,3-dihydro-1h-indole Chemical compound C1=CC=C2NCCC2=C1.C1=CC=CC2=C(C=CNO3)C3=CC=C21 ITPCCQOGYMDBHK-UHFFFAOYSA-N 0.000 claims description 4
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- 229920001727 cellulose butyrate Polymers 0.000 claims description 4
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- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 229920008347 Cellulose acetate propionate Polymers 0.000 claims description 3
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 3
- 229920001603 poly (alkyl acrylates) Polymers 0.000 claims description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 2
- VFUGUWZYXGNQHR-UHFFFAOYSA-N 2h-1,2-benzoxazine;2,3-dihydro-1h-indole Chemical compound C1=CC=C2NCCC2=C1.C1=CC=C2C=CNOC2=C1 VFUGUWZYXGNQHR-UHFFFAOYSA-N 0.000 claims description 2
- SHASOVNNKCSWPT-UHFFFAOYSA-N 2h-pyrido[2,3-e]oxazine Chemical compound C1=CN=C2C=CNOC2=C1 SHASOVNNKCSWPT-UHFFFAOYSA-N 0.000 claims description 2
- 229920002319 Poly(methyl acrylate) Polymers 0.000 claims description 2
- 230000000295 complement effect Effects 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 4
- 239000005020 polyethylene terephthalate Substances 0.000 claims 2
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 claims 2
- 229920000638 styrene acrylonitrile Polymers 0.000 claims 2
- 101100495769 Caenorhabditis elegans che-1 gene Proteins 0.000 claims 1
- 229920007962 Styrene Methyl Methacrylate Polymers 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 claims 1
- 239000010408 film Substances 0.000 description 56
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- 229920005989 resin Polymers 0.000 description 42
- 150000003254 radicals Chemical class 0.000 description 31
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 23
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- 239000000460 chlorine Substances 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 229920005372 Plexiglas® Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 206010037888 Rash pustular Diseases 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000035508 accumulation Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- GQVCNZBQZKXBMX-UHFFFAOYSA-N butan-2-one;toluene Chemical compound CCC(C)=O.CC1=CC=CC=C1 GQVCNZBQZKXBMX-UHFFFAOYSA-N 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000003486 chemical etching Methods 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000013527 degreasing agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical group C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 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
- 239000000428 dust Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000005213 imbibition Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920005613 synthetic organic polymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
- B05D5/06—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain multicolour or other optical effects
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/02—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Laminated Bodies (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Optical Filters (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71761885A | 1985-03-29 | 1985-03-29 | |
| US77975085A | 1985-09-24 | 1985-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3607759A1 true DE3607759A1 (de) | 1986-10-02 |
Family
ID=27109740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863607759 Granted DE3607759A1 (de) | 1985-03-29 | 1986-03-08 | Photochromer gegenstand aus kunststoff und verfahren zu seiner herstellung |
Country Status (11)
| Country | Link |
|---|---|
| AU (1) | AU554441B2 (pt) |
| BR (1) | BR8601298A (pt) |
| CA (1) | CA1274427C (pt) |
| DE (1) | DE3607759A1 (pt) |
| FR (1) | FR2587501B1 (pt) |
| GB (1) | GB2174711B (pt) |
| HK (1) | HK71889A (pt) |
| IT (1) | IT1191994B (pt) |
| MX (1) | MX164718B (pt) |
| MY (1) | MY101860A (pt) |
| SG (1) | SG27389G (pt) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3516568A1 (de) * | 1985-05-08 | 1986-01-23 | Optische Werke G. Rodenstock, 8000 München | Verfahren zum einfaerben von brillenglaesern aus kunststoff mit organischen farbstoffen |
| EP0331217A1 (en) * | 1988-02-02 | 1989-09-06 | Akzo N.V. | Photochromic composition |
| US9975053B1 (en) | 2017-04-28 | 2018-05-22 | Jay At Play International Hong Kong Limited | Transformable toy with reversible head |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4909963A (en) * | 1986-09-26 | 1990-03-20 | Ppg Industries, Inc. | Photochromic article |
| US4816584A (en) * | 1986-11-12 | 1989-03-28 | Ppg Industries, Inc. | Photochromic spiro(indoline)benzoxazines |
| US4831142A (en) * | 1986-09-26 | 1989-05-16 | Ppg Industries, Inc. | Spiro indoline-pyranobenzoxazinones |
| DE3852831T2 (de) * | 1987-02-02 | 1995-05-18 | Toray Industries | Photochrome Verbindung. |
| IT1223348B (it) * | 1987-11-05 | 1990-09-19 | Enichem Sintesi | Bambola o altro gioco per l'infanzia con caratteristiche fotocromatiche e relativo procedimento di preparazione |
| US5021196A (en) * | 1988-01-25 | 1991-06-04 | Ppg Industries, Inc. | Method for preparing variable-light transmittance article |
| US4968454A (en) * | 1988-01-25 | 1990-11-06 | Ppg Industries, Inc. | Variable-light transmittance article and method for preparing same |
| US4986934A (en) * | 1988-03-25 | 1991-01-22 | Ppg Industries, Inc. | Photochromic compound and articles containing the same |
| US5185390A (en) * | 1990-03-07 | 1993-02-09 | Ppg Industries, Inc. | Water strippable photochromic resin composition |
| US5130353A (en) * | 1990-03-07 | 1992-07-14 | Ppg Industries, Inc. | Method for preparing photochromic plastic article |
| IL105147A0 (en) * | 1992-09-11 | 1993-07-08 | American Optical Corp | Production of photochromic plastic lenses |
| AUPN007194A0 (en) * | 1994-12-16 | 1995-01-19 | Sola International Holdings Ltd | Method of preparing photochromic article |
| US7077985B2 (en) | 2000-05-30 | 2006-07-18 | Vision-Ease Lens | Injection molding of lens |
| US6521753B1 (en) * | 2000-05-31 | 2003-02-18 | Johnson & Johnson Vision Care, Inc. | Indolinospiropyran compounds and methods for their manufacture |
| US7858001B2 (en) | 2003-09-09 | 2010-12-28 | Insight Equity A.P.X., L.P. | Photochromic lens |
| ES2544317T3 (es) | 2003-09-09 | 2015-08-28 | Insight Equity A.P.X., Lp | Laminado de poliuretano fotocrómico |
| WO2006094313A2 (en) | 2005-03-04 | 2006-09-08 | Vision-Ease Lens | Forming method for polymeric laminated wafers comprising different film materials |
| FR2952440B1 (fr) | 2009-11-12 | 2012-05-04 | Essilor Int | Procede de fabrication d'un film plastique anti-uv avec une repartition spatiale non uniforme de l'absorbeur uv et elements optiques photochromes revetus d'un tel film plastique |
| US9081130B1 (en) | 2013-01-09 | 2015-07-14 | Insight Equity A.P.X., Lp | Photochromic polyurethane laminate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4286957A (en) * | 1979-01-10 | 1981-09-01 | Essilor International "Cie Generale D'optique" | Process of integrating a photochromic substance into an ophthalmic lens and a photochromic lens of organic material |
| DE3516568A1 (de) * | 1985-05-08 | 1986-01-23 | Optische Werke G. Rodenstock, 8000 München | Verfahren zum einfaerben von brillenglaesern aus kunststoff mit organischen farbstoffen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH662188A5 (de) * | 1983-03-16 | 1987-09-15 | Satis Vacuum Ag | Verfahren und einrichtung zur beschichtung optischer substrate mit reversiblen photochromischen eigenschaften. |
-
1986
- 1986-02-03 AU AU52944/86A patent/AU554441B2/en not_active Expired
- 1986-02-26 MX MX1684A patent/MX164718B/es unknown
- 1986-02-28 CA CA502997A patent/CA1274427C/en not_active Expired - Lifetime
- 1986-03-08 DE DE19863607759 patent/DE3607759A1/de active Granted
- 1986-03-21 BR BR8601298A patent/BR8601298A/pt not_active IP Right Cessation
- 1986-03-26 FR FR868604390A patent/FR2587501B1/fr not_active Expired - Lifetime
- 1986-03-26 IT IT67243/86A patent/IT1191994B/it active
- 1986-03-27 GB GB08607756A patent/GB2174711B/en not_active Expired
-
1987
- 1987-09-24 MY MYPI87001916A patent/MY101860A/en unknown
-
1989
- 1989-04-25 SG SG273/89A patent/SG27389G/en unknown
- 1989-09-07 HK HK718/89A patent/HK71889A/xx not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4286957A (en) * | 1979-01-10 | 1981-09-01 | Essilor International "Cie Generale D'optique" | Process of integrating a photochromic substance into an ophthalmic lens and a photochromic lens of organic material |
| US4286957B1 (pt) * | 1979-01-10 | 1991-08-13 | Essilor Int | |
| DE3516568A1 (de) * | 1985-05-08 | 1986-01-23 | Optische Werke G. Rodenstock, 8000 München | Verfahren zum einfaerben von brillenglaesern aus kunststoff mit organischen farbstoffen |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3516568A1 (de) * | 1985-05-08 | 1986-01-23 | Optische Werke G. Rodenstock, 8000 München | Verfahren zum einfaerben von brillenglaesern aus kunststoff mit organischen farbstoffen |
| EP0331217A1 (en) * | 1988-02-02 | 1989-09-06 | Akzo N.V. | Photochromic composition |
| US9975053B1 (en) | 2017-04-28 | 2018-05-22 | Jay At Play International Hong Kong Limited | Transformable toy with reversible head |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8607756D0 (en) | 1986-04-30 |
| IT1191994B (it) | 1988-03-31 |
| HK71889A (en) | 1989-09-14 |
| GB2174711B (en) | 1988-10-19 |
| SG27389G (en) | 1989-09-22 |
| CA1274427A (en) | 1990-09-25 |
| BR8601298A (pt) | 1986-12-02 |
| FR2587501A1 (fr) | 1987-03-20 |
| IT8667243A0 (it) | 1986-03-26 |
| FR2587501B1 (fr) | 1991-07-19 |
| AU554441B2 (en) | 1986-08-21 |
| CA1274427C (en) | 1990-09-25 |
| MX164718B (es) | 1992-09-21 |
| MY101860A (en) | 1992-01-31 |
| GB2174711A (en) | 1986-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: PPG INDUSTRIES OHIO, INC., CLEVELAND, OHIO, US |