JPS63222174A - フオトクロミツク化合物 - Google Patents
フオトクロミツク化合物Info
- Publication number
- JPS63222174A JPS63222174A JP5615387A JP5615387A JPS63222174A JP S63222174 A JPS63222174 A JP S63222174A JP 5615387 A JP5615387 A JP 5615387A JP 5615387 A JP5615387 A JP 5615387A JP S63222174 A JPS63222174 A JP S63222174A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- compound expressed
- photochromic
- biphenyl
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- 239000011347 resin Substances 0.000 abstract description 5
- 229920005989 resin Polymers 0.000 abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 4
- 230000003287 optical effect Effects 0.000 abstract description 4
- IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 abstract description 3
- 238000004040 coloring Methods 0.000 abstract description 3
- 239000004305 biphenyl Chemical group 0.000 abstract description 2
- 235000010290 biphenyl Nutrition 0.000 abstract description 2
- 238000005034 decoration Methods 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- 230000002427 irreversible effect Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical group C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 3
- 238000001782 photodegradation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GHRYSOFWKRRLMI-UHFFFAOYSA-N 1-naphthyloxyacetic acid Chemical compound C1=CC=C2C(OCC(=O)O)=CC=CC2=C1 GHRYSOFWKRRLMI-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- YUNFZUHREFLUTM-UHFFFAOYSA-N 1-(3,3-dimethyl-2-methylideneindol-1-yl)ethanol Chemical compound C1=CC=C2N(C(O)C)C(=C)C(C)(C)C2=C1 YUNFZUHREFLUTM-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RZCJYMOBWVJQGV-UHFFFAOYSA-N 2-naphthyloxyacetic acid Chemical compound C1=CC=CC2=CC(OCC(=O)O)=CC=C21 RZCJYMOBWVJQGV-UHFFFAOYSA-N 0.000 description 1
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical group C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- UBJLXPMBVQEKSC-UHFFFAOYSA-N spiro[1,3-dihydroindole-2,2'-chromene] Chemical compound O1C2=CC=CC=C2C=CC21NC1=CC=CC=C1C2 UBJLXPMBVQEKSC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Luminescent Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5615387A JPS63222174A (ja) | 1987-03-11 | 1987-03-11 | フオトクロミツク化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5615387A JPS63222174A (ja) | 1987-03-11 | 1987-03-11 | フオトクロミツク化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63222174A true JPS63222174A (ja) | 1988-09-16 |
| JPH0341472B2 JPH0341472B2 (enrdf_load_stackoverflow) | 1991-06-24 |
Family
ID=13019145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5615387A Granted JPS63222174A (ja) | 1987-03-11 | 1987-03-11 | フオトクロミツク化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63222174A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110950879A (zh) * | 2019-12-17 | 2020-04-03 | 浙江理工大学 | 引入刚性基团提高固态光致变色性能的螺吡喃及合成方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6425449B2 (ja) * | 2014-08-05 | 2018-11-21 | サトーホールディングス株式会社 | サーマルプリント装置及びその制御方法 |
-
1987
- 1987-03-11 JP JP5615387A patent/JPS63222174A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110950879A (zh) * | 2019-12-17 | 2020-04-03 | 浙江理工大学 | 引入刚性基团提高固态光致变色性能的螺吡喃及合成方法 |
| CN110950879B (zh) * | 2019-12-17 | 2023-07-04 | 浙江理工大学 | 引入刚性基团提高固态光致变色性能的螺吡喃及合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0341472B2 (enrdf_load_stackoverflow) | 1991-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4950176B2 (ja) | 反応性置換基を有するフォトクロミック物質 | |
| US4816584A (en) | Photochromic spiro(indoline)benzoxazines | |
| US6019914A (en) | Photochromic spirooxazine compounds, their use in the field of ophthalmic optics | |
| JPH06502180A (ja) | ホトクロミックナフトピラン | |
| JPH10503764A (ja) | ６’位にシアノ基又はフェニルスルホニル基を有し、ベンゾオキサジン核に７’，８’−縮合ベンゼン環を含むホトクロミックなスピロ［インドリン［２，３’］ベンゾオキサジン］化合物、及び該化合物の眼科用光学素子分野での使用 | |
| CN104011038B (zh) | 包括6-氨基取代的茚并稠合的萘并吡喃的光致变色材料 | |
| EP1025108A1 (en) | Photochromic spiro(indoline) fluoranthenoxazine compounds | |
| ES2236248T3 (es) | Compuestos de indolinoespiropirano y procedimiento de preparacion asociado. | |
| US4909963A (en) | Photochromic article | |
| JPS62145089A (ja) | スピロピペリジンナフトオキサジン化合物 | |
| JPS63222174A (ja) | フオトクロミツク化合物 | |
| AU604269B2 (en) | Photochromic spiro(indoline)benzoxazines and articles containing the same | |
| EP0358774B1 (en) | Novel spirooxazine compounds | |
| JP2975519B2 (ja) | 新規フォトクロミック化合物 | |
| JPH0368034B2 (enrdf_load_stackoverflow) | ||
| JPS61161286A (ja) | スピロオキサジン化合物 | |
| JPH0476087A (ja) | フォトクロミック材料 | |
| JPH0560837B2 (enrdf_load_stackoverflow) | ||
| JPH0317875B2 (enrdf_load_stackoverflow) | ||
| JP2541623B2 (ja) | 新規スピロオキサジン化合物 | |
| JP2503145B2 (ja) | フォトクロミック材料 | |
| JPS6153288A (ja) | スピロオキサジン化合物 | |
| JPH04112885A (ja) | スピロピラン化合物及びその製造方法 | |
| JPS61243087A (ja) | スピロオキサジン化合物 | |
| JPH0469672B2 (enrdf_load_stackoverflow) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |