ZA200303947B - Organic photochromic compositions of improved kinetic performance. - Google Patents
Organic photochromic compositions of improved kinetic performance. Download PDFInfo
- Publication number
- ZA200303947B ZA200303947B ZA200303947A ZA200303947A ZA200303947B ZA 200303947 B ZA200303947 B ZA 200303947B ZA 200303947 A ZA200303947 A ZA 200303947A ZA 200303947 A ZA200303947 A ZA 200303947A ZA 200303947 B ZA200303947 B ZA 200303947B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- composition
- substituted
- ether
- aryl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 57
- -1 acryloxy, methacryloxy Chemical group 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 239000000654 additive Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 230000002708 enhancing effect Effects 0.000 claims description 14
- 230000000996 additive effect Effects 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000004593 Epoxy Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 7
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000005213 imbibition Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
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- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 5
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- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 claims description 3
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
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- 239000002904 solvent Substances 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- LHXNVCCLDTYJGT-UHFFFAOYSA-N 1-(oxiran-2-ylmethoxy)propan-2-ol Chemical compound CC(O)COCC1CO1 LHXNVCCLDTYJGT-UHFFFAOYSA-N 0.000 claims description 2
- CUGZWHZWSVUSBE-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)ethanol Chemical compound OCCOCC1CO1 CUGZWHZWSVUSBE-UHFFFAOYSA-N 0.000 claims description 2
- GZPUHNGIERMRFC-UHFFFAOYSA-N 4-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1NC(=O)C2=C1C=CC=C2CC1CO1 GZPUHNGIERMRFC-UHFFFAOYSA-N 0.000 claims description 2
- VNGLVZLEUDIDQH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-methyloxirane Chemical class CC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 VNGLVZLEUDIDQH-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 claims description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 238000000518 rheometry Methods 0.000 claims description 2
- 125000005649 substituted arylene group Chemical group 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 229940124543 ultraviolet light absorber Drugs 0.000 claims description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims 1
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 claims 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
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- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims 1
- 229920013820 alkyl cellulose Polymers 0.000 claims 1
- 150000001562 benzopyrans Chemical class 0.000 claims 1
- KTPIWUHKYIJBCR-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohex-4-ene-1,2-dicarboxylate Chemical compound C1C=CCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 KTPIWUHKYIJBCR-UHFFFAOYSA-N 0.000 claims 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
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- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims 1
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- 229920005989 resin Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920003002 synthetic resin Polymers 0.000 claims 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 claims 1
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- 239000008096 xylene Substances 0.000 claims 1
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- 150000002009 diols Chemical class 0.000 description 6
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- FSYPIGPPWAJCJG-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1CO1 FSYPIGPPWAJCJG-UHFFFAOYSA-N 0.000 description 1
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- CUKYEOCBCKJPPB-UHFFFAOYSA-N oxolan-2-ylmethyl hexadecanoate Chemical class CCCCCCCCCCCCCCCC(=O)OCC1CCCO1 CUKYEOCBCKJPPB-UHFFFAOYSA-N 0.000 description 1
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- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00634—Production of filters
- B29D11/00653—Production of filters photochromic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00865—Applying coatings; tinting; colouring
- B29D11/00894—Applying coatings; tinting; colouring colouring or tinting
- B29D11/00903—Applying coatings; tinting; colouring colouring or tinting on the surface
Landscapes
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Ophthalmology & Optometry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Optical Filters (AREA)
- Eyeglasses (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Applications Claiming Priority (1)
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US09/724,145 US6433043B1 (en) | 2000-11-28 | 2000-11-28 | Removable imbibition composition of photochromic compound and kinetic enhancing additive |
Publications (1)
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ZA200303947B true ZA200303947B (en) | 2004-05-21 |
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ZA200303947A ZA200303947B (en) | 2000-11-28 | 2003-05-21 | Organic photochromic compositions of improved kinetic performance. |
Country Status (12)
Country | Link |
---|---|
US (3) | US6433043B1 (fr) |
EP (1) | EP1340108B9 (fr) |
JP (2) | JP2004514774A (fr) |
AR (1) | AR031433A1 (fr) |
AU (2) | AU2002227053B2 (fr) |
BR (1) | BR0115893A (fr) |
CA (1) | CA2429592C (fr) |
DE (1) | DE60118037T2 (fr) |
ES (1) | ES2260332T3 (fr) |
MX (1) | MXPA03004696A (fr) |
WO (1) | WO2002044258A2 (fr) |
ZA (1) | ZA200303947B (fr) |
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US6433043B1 (en) * | 2000-11-28 | 2002-08-13 | Transitions Optical, Inc. | Removable imbibition composition of photochromic compound and kinetic enhancing additive |
US7233998B2 (en) * | 2001-03-22 | 2007-06-19 | Sony Computer Entertainment Inc. | Computer architecture and software cells for broadband networks |
US8017720B2 (en) | 2005-12-16 | 2011-09-13 | Ppg Industries Ohio, Inc. | Sulfur-containing oligomers and high index polyurethanes prepared therefrom |
US7305681B2 (en) * | 2003-03-20 | 2007-12-04 | Nokia Corporation | Method and apparatus for providing multi-client support in a sip-enabled terminal |
US7342112B2 (en) * | 2003-07-01 | 2008-03-11 | Ppg Industries Ohio, Inc. | Photochromic compounds |
US8089678B2 (en) * | 2003-07-01 | 2012-01-03 | Transitions Optical, Inc | Clear to circular polarizing photochromic devices and methods of making the same |
US7256921B2 (en) * | 2003-07-01 | 2007-08-14 | Transitions Optical, Inc. | Polarizing, photochromic devices and methods of making the same |
US8518546B2 (en) | 2003-07-01 | 2013-08-27 | Transitions Optical, Inc. | Photochromic compounds and compositions |
BRPI0412278B1 (pt) | 2003-07-01 | 2018-01-30 | Transitions Optical, Inc. | Método para fabricar um recurso de alinhamento para uma tinta óptica, elemento oftálmico e elemento óptico |
US7632540B2 (en) * | 2003-07-01 | 2009-12-15 | Transitions Optical, Inc. | Alignment facilities for optical dyes |
US8211338B2 (en) | 2003-07-01 | 2012-07-03 | Transitions Optical, Inc | Photochromic compounds |
US8582192B2 (en) | 2003-07-01 | 2013-11-12 | Transitions Optical, Inc. | Polarizing photochromic articles |
US7978391B2 (en) * | 2004-05-17 | 2011-07-12 | Transitions Optical, Inc. | Polarizing, photochromic devices and methods of making the same |
US8545015B2 (en) | 2003-07-01 | 2013-10-01 | Transitions Optical, Inc. | Polarizing photochromic articles |
US8698117B2 (en) | 2003-07-01 | 2014-04-15 | Transitions Optical, Inc. | Indeno-fused ring compounds |
US8545984B2 (en) | 2003-07-01 | 2013-10-01 | Transitions Optical, Inc. | Photochromic compounds and compositions |
US9096014B2 (en) | 2003-07-01 | 2015-08-04 | Transitions Optical, Inc. | Oriented polymeric sheets exhibiting dichroism and articles containing the same |
TWI290572B (en) * | 2003-08-06 | 2007-12-01 | Lg Chemical Ltd | Primer composition for coating transparent materials and photochromic transparent materials |
US20050071828A1 (en) * | 2003-09-25 | 2005-03-31 | International Business Machines Corporation | System and method for compiling source code for multi-processor environments |
US7549145B2 (en) | 2003-09-25 | 2009-06-16 | International Business Machines Corporation | Processor dedicated code handling in a multi-processor environment |
US7523157B2 (en) * | 2003-09-25 | 2009-04-21 | International Business Machines Corporation | Managing a plurality of processors as devices |
US7389508B2 (en) * | 2003-09-25 | 2008-06-17 | International Business Machines Corporation | System and method for grouping processors and assigning shared memory space to a group in heterogeneous computer environment |
US7415703B2 (en) * | 2003-09-25 | 2008-08-19 | International Business Machines Corporation | Loading software on a plurality of processors |
US7496917B2 (en) * | 2003-09-25 | 2009-02-24 | International Business Machines Corporation | Virtual devices using a pluarlity of processors |
US7516456B2 (en) | 2003-09-25 | 2009-04-07 | International Business Machines Corporation | Asymmetric heterogeneous multi-threaded operating system |
US7478390B2 (en) * | 2003-09-25 | 2009-01-13 | International Business Machines Corporation | Task queue management of virtual devices using a plurality of processors |
US7444632B2 (en) | 2003-09-25 | 2008-10-28 | International Business Machines Corporation | Balancing computational load across a plurality of processors |
US7475257B2 (en) * | 2003-09-25 | 2009-01-06 | International Business Machines Corporation | System and method for selecting and using a signal processor in a multiprocessor system to operate as a security for encryption/decryption of data |
US7504054B2 (en) * | 2003-12-11 | 2009-03-17 | Bayer Materialscience Llc | Method of treating a plastic article |
US7097303B2 (en) * | 2004-01-14 | 2006-08-29 | Ppg Industries Ohio, Inc. | Polarizing devices and methods of making the same |
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 |
US8563213B2 (en) * | 2004-07-16 | 2013-10-22 | Transitions Optical, Inc. | Methods for producing photosensitive microparticles |
US11008418B2 (en) | 2004-09-01 | 2021-05-18 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US11248083B2 (en) | 2004-09-01 | 2022-02-15 | Ppg Industries Ohio, Inc. | Aircraft windows |
US9598527B2 (en) | 2004-09-01 | 2017-03-21 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US20090280709A1 (en) | 2004-09-01 | 2009-11-12 | Ppg Industries Ohio, Inc. | Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same |
US11591436B2 (en) | 2004-09-01 | 2023-02-28 | Ppg Industries Ohio, Inc. | Polyurethane article and methods of making the same |
US11149107B2 (en) | 2004-09-01 | 2021-10-19 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US9464169B2 (en) | 2004-09-01 | 2016-10-11 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US20090280329A1 (en) | 2004-09-01 | 2009-11-12 | Ppg Industries Ohio, Inc. | Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same |
US7887882B2 (en) * | 2005-02-09 | 2011-02-15 | Essilor International (Compagnie Generale D'optique) | Stabilized ultra-violet absorbers |
US20070259117A1 (en) * | 2006-05-04 | 2007-11-08 | Bayer Materialscience Llc | Article having photochromic properties and process for its manufacture |
CN101437875B (zh) | 2006-05-05 | 2011-05-11 | Ppg工业俄亥俄公司 | 硫醚官能的低聚多硫醇以及由其制备的制品 |
US20070257238A1 (en) * | 2006-05-05 | 2007-11-08 | Transitions Optical, Inc. | Polymerizable photochromic compositions with multiple initiators |
KR100623659B1 (ko) | 2006-05-22 | 2006-09-13 | (주)유브이테크인터내셔날 | 광호환성 플라스틱 사출성형물 코팅용 조성물 |
KR101528385B1 (ko) * | 2008-01-10 | 2015-06-11 | 오르보테크 엘티디. | 다중 미러 조정 시스템 |
US7867577B2 (en) * | 2008-05-15 | 2011-01-11 | Essilor International (Compagnie Generale D'optique) | Sulfur modified silanes for the elaboration of high refractive index materials |
US20100014010A1 (en) * | 2008-06-27 | 2010-01-21 | Transitions Optical, Inc. | Formulations comprising mesogen containing compounds |
US20090326186A1 (en) * | 2008-06-27 | 2009-12-31 | Transitions Optical, Inc. | Mesogen containing compounds |
US7910020B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Liquid crystal compositions comprising mesogen containing compounds |
US8623238B2 (en) | 2008-06-27 | 2014-01-07 | Transitions Optical, Inc. | Mesogenic stabilizers |
US8613868B2 (en) | 2008-06-27 | 2013-12-24 | Transitions Optical, Inc | Mesogenic stabilizers |
US8349210B2 (en) | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
US7910019B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Mesogen containing compounds |
US8431039B2 (en) | 2008-06-27 | 2013-04-30 | Transitions Optical, Inc. | Mesogenic stabilizers |
US8628685B2 (en) | 2008-06-27 | 2014-01-14 | Transitions Optical, Inc | Mesogen-containing compounds |
JP5338164B2 (ja) * | 2008-07-14 | 2013-11-13 | 三菱瓦斯化学株式会社 | 新規なテトラチアスピロ化合物 |
US9475901B2 (en) | 2009-12-08 | 2016-10-25 | Transitions Optical, Inc. | Photoalignment materials having improved adhesion |
CA2836743C (fr) | 2011-06-06 | 2016-06-14 | Transitions Optical, Inc. | Articles photochromiques polarisants |
CA2859195C (fr) * | 2011-12-14 | 2016-09-27 | Semprus Biosciences Corp. | Processus d'impregnation destine a la modification de la surface de lentilles de contact |
WO2013090780A1 (fr) | 2011-12-14 | 2013-06-20 | Semprus Biosciences Corp. | Lentilles de contact à surface modifiée |
JP2015502437A (ja) | 2011-12-14 | 2015-01-22 | センプラス・バイオサイエンシーズ・コーポレイションSemprus Biosciences Corp. | ランタニド又は遷移金属酸化剤を用いて改質したシリコーンヒドロゲルコンタクトレンズ |
CA2859047C (fr) * | 2011-12-14 | 2017-03-21 | Semprus Biosciences Corp. | Processus redox destines a la modification de lentilles de contact |
US8734033B2 (en) | 2012-03-27 | 2014-05-27 | Ppg Industries Ohio, Inc. | Optical mechanism with indexing stage with at least one fixed diameter apodized aperture and method of making same |
US9568643B2 (en) | 2012-12-13 | 2017-02-14 | Ppg Industries Ohio, Inc. | Polyurethane urea-containing compositions and optical articles and methods for preparing them |
US20140264979A1 (en) | 2013-03-13 | 2014-09-18 | Transitions Opticals, Inc. | Method of preparing photochromic-dichroic films having reduced optical distortion |
WO2014167611A1 (fr) * | 2013-04-12 | 2014-10-16 | ロート製薬株式会社 | Composition pour lentilles de contact, et paquet de lentilles de contact mettant en œuvre celle-ci |
CN103513315B (zh) * | 2013-10-24 | 2016-04-13 | 京东方科技集团股份有限公司 | 彩色滤光片返修工艺 |
PL2902148T3 (pl) | 2013-11-25 | 2020-03-31 | Preco, Inc. | Obudowa galvo o wysokim zagęszczeniu do stosowania z wieloma wiązkami laserowymi, układ galvo i system obróbki wiązką laserową z taką obudową |
EP3201292B1 (fr) | 2014-09-30 | 2018-08-01 | Transitions Optical, Inc. | Absorbeurs de lumière ultraviolette |
US9874811B2 (en) | 2015-09-10 | 2018-01-23 | Samsung Electronics Co., Ltd. | Photopolymer composition for holographic recording |
EP3368927B1 (fr) | 2015-10-30 | 2024-10-16 | Transitions Optical, Inc. | Article optique avec proprietes gradient de propriétés influencant la lumiere et son procédé de fabrication |
EP3368926B1 (fr) | 2015-10-30 | 2024-03-06 | Transitions Optical Ltd. | Procédé de réalisation d'un article optique avec système d'impression à jet d'encre |
KR102303085B1 (ko) * | 2016-10-11 | 2021-09-15 | 미쯔이가가꾸가부시끼가이샤 | 광학 재료용 중합성 조성물 및 그의 용도 |
WO2018102266A1 (fr) | 2016-12-02 | 2018-06-07 | 3M Innovative Properties Company | Articles photochromiques contenant un matériau poreux avec un colorant photochromique et un fluide, procédés de fabrication et d'utilisation |
MX2019006555A (es) | 2016-12-23 | 2019-08-21 | Transitions Optical Ltd | Metodo de fabricacion de una lente con propiedades de gradiente usando tecnologia de imbibicion. |
US10884288B2 (en) | 2016-12-30 | 2021-01-05 | Transitions Optical, Ltd. | Polarizing article and method of forming a polarizing article |
CN106723117A (zh) * | 2016-12-30 | 2017-05-31 | 绵阳八叶长风工业设计有限公司 | 开心果快速压裂装置 |
JP7033605B2 (ja) | 2017-03-01 | 2022-03-10 | ヤンガー・マニュファクチャリング・カンパニー・ドゥーイング/ビジネス/アズ・ヤンガー・オプティックス | フォトクロミックアイウェアレンズの製造方法およびフォトクロミックアイウェア製品 |
US10866455B2 (en) | 2017-10-19 | 2020-12-15 | Ppg Industries Ohio, Inc. | Display devices including photochromic-dichroic compounds and dichroic compounds |
CN114075369B (zh) * | 2020-08-19 | 2023-08-18 | 中国石油化工股份有限公司 | 一种刺激感应材料及其制备方法 |
JP2022151089A (ja) * | 2021-03-26 | 2022-10-07 | ホヤ レンズ タイランド リミテッド | インデノ縮合ナフトピラン化合物の粒子、重合性組成物の製造方法及びフォトクロミック物品の製造方法 |
JP2022151088A (ja) * | 2021-03-26 | 2022-10-07 | ホヤ レンズ タイランド リミテッド | インデノ縮合ナフトピラン化合物の粒子、重合性組成物の製造方法及びフォトクロミック物品の製造方法 |
EP4147863A1 (fr) | 2021-09-10 | 2023-03-15 | Carl Zeiss Vision International GmbH | Procédé et composition pour teindre un substrat de verre de lunettes |
DE102022110731B4 (de) * | 2022-05-02 | 2023-12-07 | Rodenstock Gmbh | Verfahren zum Versehen eines Substrats mit einer Einfärbung und einer Funktionsfärbung |
Family Cites Families (82)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US578602A (en) * | 1897-03-09 | Vacuum-brake | ||
US3169945A (en) | 1956-04-13 | 1965-02-16 | Union Carbide Corp | Lactone polyesters |
US3166945A (en) * | 1961-07-03 | 1965-01-26 | Haldex Ab | Impulse generator |
US3361706A (en) | 1964-03-06 | 1968-01-02 | American Cyanamid Co | Control of the photochromic return rate of (arylazo) thioformic arylhydrazidates |
US3567605A (en) | 1966-03-30 | 1971-03-02 | Ralph S Becker | Photochemical process |
GB1186987A (en) | 1967-08-30 | 1970-04-08 | Fuji Photo Film Co Ltd | Photochromic Compounds |
JPS4948631B1 (fr) | 1968-10-28 | 1974-12-23 | ||
US3627690A (en) * | 1969-10-01 | 1971-12-14 | Itek Corp | Photochromic naphthopyran compositions |
FR2129859A1 (en) * | 1971-03-17 | 1972-11-03 | Saint Gobain | Photochromic polyvinyl butyral - glazing interlayer film by dipping in soln of photochrome and plasticiser |
US3707347A (en) * | 1971-08-17 | 1972-12-26 | Owens Illinois Inc | Staining plastic surfaces |
US3860388A (en) * | 1972-09-25 | 1975-01-14 | John M Haigh | Disperse dye transfer through polyolefin release layer to non-porous thermoplastic sheet dyed thereby |
US3866242A (en) | 1972-10-27 | 1975-02-18 | Goodyear Aerospace Corp | Protective shield |
US4271224A (en) * | 1976-12-26 | 1981-06-02 | Dai Nippon Insatsu Kabushiki Kaisha | Transfer sheet with resist portions |
DE2750984C3 (de) * | 1977-11-15 | 1980-10-30 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung eines ein- oder mehrfarbig gefärbten Flächengebildes aus Kunststoff |
US4238524A (en) * | 1978-03-06 | 1980-12-09 | American Optical Corporation | Process for identification marking clear plastic articles |
US4342668A (en) | 1978-09-08 | 1982-08-03 | American Optical Corporation | Photochromic compounds |
US4215010A (en) | 1978-09-08 | 1980-07-29 | American Optical Corporation | Photochromic compounds |
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 |
US4360653A (en) | 1981-10-23 | 1982-11-23 | Ppg Industries, Inc. | Polymerizate of (allyl carbonate) and aliphatic polyurethane having acrylic unsaturation |
US4720356A (en) | 1982-03-22 | 1988-01-19 | American Optical Corporation | Photochromic composition resistant to fatigue |
JPS60107030A (ja) * | 1983-11-15 | 1985-06-12 | Seiko Epson Corp | 合成樹脂製フォトクロミックレンズ |
JPS61263982A (ja) | 1985-01-25 | 1986-11-21 | Mitsubishi Chem Ind Ltd | 3,3−ジメチル−スピロ〔インドリノ−2,3′−ナフト〔2,1−b〕(1,4)オキサジン〕系化合物 |
DE3516568A1 (de) * | 1985-05-08 | 1986-01-23 | Optische Werke G. Rodenstock, 8000 München | Verfahren zum einfaerben von brillenglaesern aus kunststoff mit organischen farbstoffen |
US4880667A (en) * | 1985-09-24 | 1989-11-14 | Ppg Industries, Inc. | Photochromic plastic article and method for preparing same |
GB8611837D0 (en) | 1986-05-15 | 1986-06-25 | Plessey Co Plc | Photochromic spiropyran compounds |
GB8614680D0 (en) | 1986-06-17 | 1986-07-23 | Plessey Co Plc | Photoreactive lenses |
US4816584A (en) | 1986-11-12 | 1989-03-28 | Ppg Industries, Inc. | Photochromic spiro(indoline)benzoxazines |
JPS63175094A (ja) * | 1987-01-16 | 1988-07-19 | Toray Ind Inc | ホトクロミック性を有する組成物 |
CA1340939C (fr) | 1987-02-02 | 2000-03-28 | Ryojiro Akashi | Compose photochromique |
US4931219A (en) | 1987-07-27 | 1990-06-05 | Ppg Industries, Inc. | Photochromic compound and articles containing the same |
US4931220A (en) | 1987-11-24 | 1990-06-05 | Ppg Industries, Inc. | Organic photochromic pigment particulates |
US5252742A (en) | 1989-02-28 | 1993-10-12 | Otsuka Kagaku Kabushiki Kaisha | Spiropyran compounds |
US4994208A (en) | 1989-04-18 | 1991-02-19 | Ppg Industries, Inc. | Photochromic polymeric article |
US5200883A (en) | 1989-06-23 | 1993-04-06 | Kabushiki Kaisha Toshiba | Portable computer having an external battery mounting portion and optional device mounting portion |
EP0420397B1 (fr) | 1989-07-28 | 1995-11-29 | Wako Pure Chemical Industries Ltd | Dérivés de fulgimide |
JP2758936B2 (ja) * | 1989-08-09 | 1998-05-28 | 呉羽化学工業株式会社 | フォトクロミック化合物 |
EP0470264B1 (fr) | 1990-02-23 | 1996-05-15 | Otsuka Kagaku Kabushiki Kaisha | Benzoselenazoline-spiro-vinylpyrane et polymere contenant un tel compose |
US5185390A (en) | 1990-03-07 | 1993-02-09 | Ppg Industries, Inc. | Water strippable photochromic resin composition |
US5066818A (en) | 1990-03-07 | 1991-11-19 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
US5373033A (en) | 1990-04-20 | 1994-12-13 | Sola International Holdings Limited | Casting composition |
US5238981A (en) | 1992-02-24 | 1993-08-24 | Transitions Optical, Inc. | Photochromic naphthopyrans |
US5462698A (en) | 1992-03-03 | 1995-10-31 | Tokuyama Corporation | Photochromic composition |
JP3016533B2 (ja) * | 1992-03-03 | 2000-03-06 | 株式会社トクヤマ | フォトクロミック組成物 |
EP0728315B1 (fr) | 1992-09-25 | 1999-12-22 | PPG Industries Ohio, Inc. | Compositions photochromiques a resistance a la fatigue amelioree |
US5274132A (en) | 1992-09-30 | 1993-12-28 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
DE59304881D1 (de) | 1992-10-15 | 1997-02-06 | Ciba Geigy Ag | Polymerisierbare photochrome Napthacendione, Polymere dieser Monomeren, Verfahren zu deren Herstellung, und deren Verwendung |
US5405958A (en) | 1992-12-21 | 1995-04-11 | Transitions Optical, Inc. | Photochromic spiro(indoline)naphthoxazine compounds |
AU665480B2 (en) | 1993-01-29 | 1996-01-04 | Tokuyama Corporation | Polymerizable composition, polymer, organic glass and ophthalmic lens |
WO1994020869A1 (fr) | 1993-03-12 | 1994-09-15 | Ppg Industries, Inc. | Nouveaux benzopyrannes |
US5552091A (en) | 1993-03-12 | 1996-09-03 | Ppg Industries, Inc. | Benzopyran compounds |
US5578252A (en) | 1993-06-21 | 1996-11-26 | Transitions Optical, Inc. | Photochromic substituted naphthopyran compounds |
US5552090A (en) | 1993-06-21 | 1996-09-03 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
US5384077A (en) | 1993-06-21 | 1995-01-24 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
US5466398A (en) | 1993-06-21 | 1995-11-14 | Transitions Optical, Inc. | Photochromic substituted naphthopyran compounds |
US5458814A (en) | 1993-12-09 | 1995-10-17 | Transitions Optical, Inc. | Substituted naphthopyrans |
JPH07178831A (ja) * | 1993-12-22 | 1995-07-18 | Tokuyama Corp | フォトクロミック成形体の製造方法 |
US5451344A (en) | 1994-04-08 | 1995-09-19 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
JP3471073B2 (ja) | 1994-04-27 | 2003-11-25 | 株式会社トクヤマ | フォトクロミック組成物 |
US5514817A (en) | 1994-08-04 | 1996-05-07 | Ppg Industries, Inc. | Substituted phenanthropyrans |
US5760100B1 (en) | 1994-09-06 | 2000-11-14 | Ciba Vision Corp | Extended wear ophthalmic lens |
US5645767A (en) | 1994-11-03 | 1997-07-08 | Transitions Optical, Inc. | Photochromic indeno-fused naphthopyrans |
US5962617A (en) | 1995-02-02 | 1999-10-05 | Simula Inc. | Impact resistant polyurethane and method of manufacture thereof |
JPH08311441A (ja) | 1995-05-24 | 1996-11-26 | Tokuyama Corp | フォトクロミック硬化体の製造方法 |
JPH08320534A (ja) | 1995-05-25 | 1996-12-03 | Tokuyama Corp | フォトクロミック硬化性組成物 |
US5656206A (en) | 1995-06-14 | 1997-08-12 | Transitions Optical, Inc. | Substituted naphthopyrans |
US5658501A (en) | 1995-06-14 | 1997-08-19 | Transitions Optical, Inc. | Substituted naphthopyrans |
US5658500A (en) | 1995-06-14 | 1997-08-19 | Transitions Optical, Inc. | Substituted naphthopyrans |
US5753146A (en) | 1996-03-29 | 1998-05-19 | Transitions Optical, Inc. | Photochromic naphthopyran compositions of neutral color |
US5770115A (en) | 1996-04-19 | 1998-06-23 | Ppg Industries, Inc. | Photochromic naphthopyran compositions of improved fatigue resistance |
US6057039A (en) * | 1996-04-26 | 2000-05-02 | Seiko Epson Corporation | Coating composition |
US5811506A (en) | 1997-02-03 | 1998-09-22 | Simula Inc. | Extrudable thermoplastic elastomeric urea-extended polyurethane |
US5698141A (en) | 1996-06-17 | 1997-12-16 | Ppg Industries, Inc. | Photochromic heterocyclic fused indenonaphthopyrans |
US5789015A (en) * | 1996-06-26 | 1998-08-04 | Innotech, Inc. | Impregnation of plastic substrates with photochromic additives |
SG54538A1 (en) | 1996-08-05 | 1998-11-16 | Hoya Corp | Soft contact lens with high moisture content and method for producing the same |
FR2758336B1 (fr) | 1997-01-10 | 1999-02-12 | Oreal | Utilisation d'un composant particulier pour ameliorer le photochromisme d'un compose initialement photochrome |
US5975696A (en) | 1997-05-12 | 1999-11-02 | Kohan; George | Process for rendering plastic substrate photochromic |
US6268055B1 (en) * | 1997-12-08 | 2001-07-31 | Ppg Industries Ohio, Inc. | Photochromic epoxy resin coating composition and articles having such a coating |
US5962619A (en) | 1998-03-16 | 1999-10-05 | Arco Chemical Technology, L.P. | Process for making clear polyurethane/urea elastomers |
US6436525B1 (en) * | 1998-12-11 | 2002-08-20 | Ppg Industries Ohio, Inc. | Polyanhydride photochromic coating composition and photochromic articles |
US6432544B1 (en) * | 1998-12-18 | 2002-08-13 | Ppg Industries Ohio, Inc. | Aminoplast resin photochromic coating composition and photochromic articles |
US6719812B1 (en) * | 2000-04-11 | 2004-04-13 | Gentex Optics, Inc. | Infusion of dye using a plasticizer |
US6433043B1 (en) * | 2000-11-28 | 2002-08-13 | Transitions Optical, Inc. | Removable imbibition composition of photochromic compound and kinetic enhancing additive |
-
2000
- 2000-11-28 US US09/724,145 patent/US6433043B1/en not_active Expired - Lifetime
-
2001
- 2001-11-15 JP JP2002546619A patent/JP2004514774A/ja active Pending
- 2001-11-15 BR BR0115893-7A patent/BR0115893A/pt not_active Application Discontinuation
- 2001-11-15 WO PCT/US2001/044925 patent/WO2002044258A2/fr active IP Right Grant
- 2001-11-15 ES ES01996013T patent/ES2260332T3/es not_active Expired - Lifetime
- 2001-11-15 CA CA002429592A patent/CA2429592C/fr not_active Expired - Fee Related
- 2001-11-15 DE DE60118037T patent/DE60118037T2/de not_active Expired - Lifetime
- 2001-11-15 AU AU2002227053A patent/AU2002227053B2/en not_active Ceased
- 2001-11-15 EP EP01996013A patent/EP1340108B9/fr not_active Expired - Lifetime
- 2001-11-15 MX MXPA03004696A patent/MXPA03004696A/es active IP Right Grant
- 2001-11-15 AU AU2705302A patent/AU2705302A/xx active Pending
- 2001-11-28 AR ARP010105547A patent/AR031433A1/es unknown
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2002
- 2002-06-14 US US10/172,665 patent/US6713536B2/en not_active Expired - Lifetime
-
2003
- 2003-05-21 ZA ZA200303947A patent/ZA200303947B/en unknown
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- 2004-01-16 US US10/759,287 patent/US7147889B2/en not_active Expired - Lifetime
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- 2005-08-23 JP JP2005241891A patent/JP2006052408A/ja active Pending
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JP2004514774A (ja) | 2004-05-20 |
DE60118037T2 (de) | 2006-09-28 |
DE60118037D1 (de) | 2006-05-11 |
US6433043B1 (en) | 2002-08-13 |
ES2260332T3 (es) | 2006-11-01 |
US20030045612A1 (en) | 2003-03-06 |
EP1340108A2 (fr) | 2003-09-03 |
US20040149966A1 (en) | 2004-08-05 |
AR031433A1 (es) | 2003-09-24 |
WO2002044258A3 (fr) | 2003-02-27 |
MXPA03004696A (es) | 2003-08-19 |
CA2429592C (fr) | 2008-02-05 |
US7147889B2 (en) | 2006-12-12 |
BR0115893A (pt) | 2004-02-25 |
EP1340108B1 (fr) | 2006-03-15 |
AU2705302A (en) | 2002-06-11 |
WO2002044258A2 (fr) | 2002-06-06 |
AU2002227053B2 (en) | 2005-02-17 |
JP2006052408A (ja) | 2006-02-23 |
CA2429592A1 (fr) | 2002-06-06 |
EP1340108B9 (fr) | 2006-08-23 |
US6713536B2 (en) | 2004-03-30 |
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