JPH0355511B2 - - Google Patents
Info
- Publication number
- JPH0355511B2 JPH0355511B2 JP31938388A JP31938388A JPH0355511B2 JP H0355511 B2 JPH0355511 B2 JP H0355511B2 JP 31938388 A JP31938388 A JP 31938388A JP 31938388 A JP31938388 A JP 31938388A JP H0355511 B2 JPH0355511 B2 JP H0355511B2
- Authority
- JP
- Japan
- Prior art keywords
- nickel
- tetra
- butylammonium
- parts
- dithiophenolate
- 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.)
- Expired
Links
- -1 benzenedithiol metal complex Chemical class 0.000 claims description 21
- 229920003023 plastic Polymers 0.000 claims description 21
- 239000004033 plastic Substances 0.000 claims description 21
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000006096 absorbing agent Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- 239000010408 film Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical class SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- YFUYVQWZEJRMBK-UHFFFAOYSA-N nickel(2+);tetrabutylazanium Chemical compound [Ni+2].CCCC[N+](CCCC)(CCCC)CCCC YFUYVQWZEJRMBK-UHFFFAOYSA-N 0.000 description 10
- 150000004696 coordination complex Chemical class 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MSSNSTXFTUNKQH-UHFFFAOYSA-N 3,4,5,6-tetrachlorobenzene-1,2-dithiol Chemical compound SC1=C(S)C(Cl)=C(Cl)C(Cl)=C1Cl MSSNSTXFTUNKQH-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical group CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
- AJCUDWCLDWDLNY-UHFFFAOYSA-N 3,6-dichlorobenzene-1,2-dithiol Chemical compound SC1=C(S)C(Cl)=CC=C1Cl AJCUDWCLDWDLNY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 208000003464 asthenopia Diseases 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000004313 glare Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical group CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 2
- 150000002815 nickel Chemical group 0.000 description 2
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 238000003466 welding Methods 0.000 description 2
- PCGDBWLKAYKBTN-UHFFFAOYSA-N 1,2-dithiole Chemical compound C1SSC=C1 PCGDBWLKAYKBTN-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- NDRLGEJTTIQUJP-UHFFFAOYSA-N 3,4,6-tribromobenzene-1,2-dithiol Chemical compound SC1=C(S)C(Br)=C(Br)C=C1Br NDRLGEJTTIQUJP-UHFFFAOYSA-N 0.000 description 1
- IOZGSEUZOKDYJZ-UHFFFAOYSA-N 3,4,6-trichlorobenzene-1,2-dithiol Chemical compound SC1=C(S)C(Cl)=C(Cl)C=C1Cl IOZGSEUZOKDYJZ-UHFFFAOYSA-N 0.000 description 1
- ZRJGHERVCOGHOZ-UHFFFAOYSA-N 3,6-dibromobenzene-1,2-dithiol Chemical compound SC1=C(S)C(Br)=CC=C1Br ZRJGHERVCOGHOZ-UHFFFAOYSA-N 0.000 description 1
- ZDTOSZNUKHUNAK-UHFFFAOYSA-N 3-chlorobenzene-1,2-dithiol Chemical compound SC1=CC=CC(Cl)=C1S ZDTOSZNUKHUNAK-UHFFFAOYSA-N 0.000 description 1
- NIAAGQAEVGMHPM-UHFFFAOYSA-N 4-methylbenzene-1,2-dithiol Chemical compound CC1=CC=C(S)C(S)=C1 NIAAGQAEVGMHPM-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004951 benzene Polymers 0.000 description 1
- JRNVQLOKVMWBFR-UHFFFAOYSA-L benzene-1,2-dithiolate Chemical compound [S-]C1=CC=CC=C1[S-] JRNVQLOKVMWBFR-UHFFFAOYSA-L 0.000 description 1
- 150000001555 benzenes Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 238000005338 heat storage Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Polymers [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31938388A JPH02659A (ja) | 1988-12-20 | 1988-12-20 | 新規なハロゲン置換ベンゼンジチオール金属錯体を含有するプラスチック組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31938388A JPH02659A (ja) | 1988-12-20 | 1988-12-20 | 新規なハロゲン置換ベンゼンジチオール金属錯体を含有するプラスチック組成物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20157481A Division JPS58105996A (ja) | 1981-12-16 | 1981-12-16 | 新規なハロゲン置換ベンゼンジチオール金属錯体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02659A JPH02659A (ja) | 1990-01-05 |
| JPH0355511B2 true JPH0355511B2 (enrdf_load_stackoverflow) | 1991-08-23 |
Family
ID=18109545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31938388A Granted JPH02659A (ja) | 1988-12-20 | 1988-12-20 | 新規なハロゲン置換ベンゼンジチオール金属錯体を含有するプラスチック組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02659A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3206940B2 (ja) * | 1991-12-16 | 2001-09-10 | ダイセル化学工業株式会社 | 近赤外線吸収メタクリル系樹脂組成物及びその成形体 |
-
1988
- 1988-12-20 JP JP31938388A patent/JPH02659A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02659A (ja) | 1990-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69024541T2 (de) | Fotochrome Indolino-spiro-oxazine mit einem fünfgliedrigen Ring, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende fotochrome Zusammensetzungen und Gegenstände | |
| DE68918514T2 (de) | Photochromische Verbindung, Verfahren zu ihrer Herstellung, ihre Verwendung und diese enthaltende photochromische Zubereitung. | |
| JPH0374389A (ja) | インドリノースピロキノキサリノオキサジン系フォトクロミック化合物、それらの製造法、そのような化合物を含むフォトクロミック組成物および物品 | |
| 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 | |
| WO1985002619A1 (en) | Photochromic substances | |
| DE69419041T2 (de) | Verfahren zur herstellung von photochromen annelierten spiro[indolin-[2,3']-benzoxazin]verbindungen | |
| US4508655A (en) | Metal complexes of halogen-substituted o-benzenedithiols | |
| JPH0442396B2 (enrdf_load_stackoverflow) | ||
| JPH0355511B2 (enrdf_load_stackoverflow) | ||
| JPH0121831B2 (enrdf_load_stackoverflow) | ||
| JPH0133112B2 (enrdf_load_stackoverflow) | ||
| JPH0749433B2 (ja) | 近赤外線吸収剤用の新規なｔ−ブチル置換ベンゼンチオールニッケル錯体およびこの錯体を含有するプラスチック組成物 | |
| CN1283745C (zh) | 杂环取代的螺噁嗪类化合物光致变色纳米复合材料及制品 | |
| CA1201718A (en) | Metal complexes of halogen-substituted o- benzenedithiols | |
| JP2000344693A (ja) | ジアリールエテン系化合物及びフォトクロミック有機膜 | |
| JPS62243609A (ja) | 親水性−疎水性熱可逆型重合体及びその製造方法 | |
| JPH0559025A (ja) | ジアリールエテン系化合物 | |
| CN117088804B (zh) | 一种紫罗精衍生物及其制备方法和应用 | |
| JPS63227597A (ja) | ビス（ジチオベンジル）ニツケル錯体化合物 | |
| US3575872A (en) | Selenocarbazonates and their use as photochromic materials | |
| JPS61263935A (ja) | ジアリルエテン誘導体 | |
| JPH0413354B2 (enrdf_load_stackoverflow) | ||
| JPS6330584A (ja) | フオトクロミツク物質 | |
| JPH0569838B2 (enrdf_load_stackoverflow) | ||
| KR20210000936A (ko) | 트리아진 화합물의 제조방법 |