JPH01152182A - フォトクロミック材料およびその製造方法 - Google Patents
フォトクロミック材料およびその製造方法Info
- Publication number
- JPH01152182A JPH01152182A JP31163587A JP31163587A JPH01152182A JP H01152182 A JPH01152182 A JP H01152182A JP 31163587 A JP31163587 A JP 31163587A JP 31163587 A JP31163587 A JP 31163587A JP H01152182 A JPH01152182 A JP H01152182A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- component
- photochromic
- compound
- photochromic properties
- 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
- 229920005989 resin Polymers 0.000 title claims abstract description 64
- 239000011347 resin Substances 0.000 title claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 229920000642 polymer Polymers 0.000 claims abstract description 53
- 239000002245 particle Substances 0.000 claims abstract description 31
- 239000010419 fine particle Substances 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- 238000000576 coating method Methods 0.000 claims description 5
- 239000002612 dispersion medium Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 4
- 229920003169 water-soluble polymer Polymers 0.000 claims description 4
- UOFGSWVZMUXXIY-UHFFFAOYSA-N 1,5-Diphenyl-3-thiocarbazone Chemical compound C=1C=CC=CC=1N=NC(=S)NNC1=CC=CC=C1 UOFGSWVZMUXXIY-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 238000000137 annealing Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 abstract description 13
- 238000002156 mixing Methods 0.000 abstract description 6
- 229920000620 organic polymer Polymers 0.000 abstract description 4
- 239000000470 constituent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 23
- 239000011230 binding agent Substances 0.000 description 8
- -1 ethylene, ethylene Chemical class 0.000 description 6
- 241000122205 Chamaeleonidae Species 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229920005822 acrylic binder Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31163587A JPH01152182A (ja) | 1987-12-08 | 1987-12-08 | フォトクロミック材料およびその製造方法 |
| CA000557885A CA1340939C (en) | 1987-02-02 | 1988-02-01 | Photochromic compound |
| US07/151,601 US4929693A (en) | 1987-02-02 | 1988-02-02 | Photochromic compound |
| US07/742,079 US5166345A (en) | 1987-02-02 | 1991-08-07 | Photochromic compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31163587A JPH01152182A (ja) | 1987-12-08 | 1987-12-08 | フォトクロミック材料およびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01152182A true JPH01152182A (ja) | 1989-06-14 |
| JPH0567675B2 JPH0567675B2 (enrdf_load_stackoverflow) | 1993-09-27 |
Family
ID=18019640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31163587A Granted JPH01152182A (ja) | 1987-02-02 | 1987-12-08 | フォトクロミック材料およびその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01152182A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991012279A1 (fr) * | 1990-02-08 | 1991-08-22 | Otsuka Kagaku Kabushiki Kaisha | Compose spiropyranique a poids moleculaire eleve |
| JP2002020972A (ja) * | 2000-07-07 | 2002-01-23 | Daiwabo Co Ltd | 紫外線遮蔽性に優れたフォトクロミック布帛類 |
| WO2014007154A1 (ja) * | 2012-07-06 | 2014-01-09 | 三井化学株式会社 | 重合体粒子およびその用途 |
| WO2018070383A1 (ja) | 2016-10-11 | 2018-04-19 | 三井化学株式会社 | 光学材料用重合性組成物およびその用途 |
| WO2020158813A1 (ja) | 2019-01-30 | 2020-08-06 | 三井化学株式会社 | 光学材料用重合性組成物の製造方法 |
| WO2021241596A1 (ja) | 2020-05-28 | 2021-12-02 | 株式会社トクヤマ | 光学材料用化合物、硬化性組成物、硬化体、及び光学物品 |
| US12275813B2 (en) | 2017-12-15 | 2025-04-15 | Mitsui Chemicals, Inc. | Polymerizable composition for optical materials and application of same |
-
1987
- 1987-12-08 JP JP31163587A patent/JPH01152182A/ja active Granted
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991012279A1 (fr) * | 1990-02-08 | 1991-08-22 | Otsuka Kagaku Kabushiki Kaisha | Compose spiropyranique a poids moleculaire eleve |
| US5241027A (en) * | 1990-02-08 | 1993-08-31 | Otsuka Kagaku Kabushiki Kaisha | Macromolecular spiropyran compounds |
| JP2002020972A (ja) * | 2000-07-07 | 2002-01-23 | Daiwabo Co Ltd | 紫外線遮蔽性に優れたフォトクロミック布帛類 |
| WO2014007154A1 (ja) * | 2012-07-06 | 2014-01-09 | 三井化学株式会社 | 重合体粒子およびその用途 |
| CN104379677A (zh) * | 2012-07-06 | 2015-02-25 | 三井化学株式会社 | 聚合物粒子及其用途 |
| JPWO2014007154A1 (ja) * | 2012-07-06 | 2016-06-02 | 三井化学株式会社 | 重合体粒子およびその用途 |
| WO2018070383A1 (ja) | 2016-10-11 | 2018-04-19 | 三井化学株式会社 | 光学材料用重合性組成物およびその用途 |
| KR20190051005A (ko) | 2016-10-11 | 2019-05-14 | 미쯔이가가꾸가부시끼가이샤 | 광학 재료용 중합성 조성물 및 그의 용도 |
| US11639413B2 (en) | 2016-10-11 | 2023-05-02 | Mitsui Chemicals, Inc. | Polymerizable composition for optical materials and application of same |
| US12275813B2 (en) | 2017-12-15 | 2025-04-15 | Mitsui Chemicals, Inc. | Polymerizable composition for optical materials and application of same |
| WO2020158813A1 (ja) | 2019-01-30 | 2020-08-06 | 三井化学株式会社 | 光学材料用重合性組成物の製造方法 |
| US11866648B2 (en) | 2019-01-30 | 2024-01-09 | Mitsui Chemicals, Inc. | Process for producing polymerizable composition for optical materials |
| WO2021241596A1 (ja) | 2020-05-28 | 2021-12-02 | 株式会社トクヤマ | 光学材料用化合物、硬化性組成物、硬化体、及び光学物品 |
| KR20230016624A (ko) | 2020-05-28 | 2023-02-02 | 가부시끼가이샤 도꾸야마 | 광학 재료용 화합물, 경화성 조성물, 경화체, 및 광학 물품 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0567675B2 (enrdf_load_stackoverflow) | 1993-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |