JPH0125727B2 - - Google Patents
Info
- Publication number
- JPH0125727B2 JPH0125727B2 JP6371185A JP6371185A JPH0125727B2 JP H0125727 B2 JPH0125727 B2 JP H0125727B2 JP 6371185 A JP6371185 A JP 6371185A JP 6371185 A JP6371185 A JP 6371185A JP H0125727 B2 JPH0125727 B2 JP H0125727B2
- Authority
- JP
- Japan
- Prior art keywords
- styrene
- reaction
- refractive index
- formula
- fluorine
- 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000463 material Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007818 Grignard reagent Substances 0.000 description 5
- 238000004891 communication Methods 0.000 description 5
- 230000006854 communication Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920000620 organic polymer Polymers 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- -1 1-(pentafluorophenyl)ethyl- d4 -alcohol Chemical compound 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 238000005253 cladding Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- WACNXHCZHTVBJM-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene Chemical compound FC1=CC(F)=C(F)C(F)=C1F WACNXHCZHTVBJM-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical class CC=O IKHGUXGNUITLKF-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 125000001743 benzylic group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- IKHGUXGNUITLKF-MZCSYVLQSA-N 1,2,2,2-tetradeuterioethanone Chemical compound [2H]C(=O)C([2H])([2H])[2H] IKHGUXGNUITLKF-MZCSYVLQSA-N 0.000 description 1
- PPBRXRYQALVLMV-GDALLCCDSA-N 1,2,3,4,5-pentadeuterio-6-(1,2,2-trideuterioethenyl)benzene Chemical group [2H]C([2H])=C([2H])C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] PPBRXRYQALVLMV-GDALLCCDSA-N 0.000 description 1
- AITNMTXHTIIIBB-RHQRLBAQSA-N 1-bromo-2,3,5,6-tetradeuterio-4-fluorobenzene Chemical compound [2H]C1=C([2H])C(Br)=C([2H])C([2H])=C1F AITNMTXHTIIIBB-RHQRLBAQSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-FIBGUPNXSA-N Acetyl chloride-d3 Chemical compound [2H]C([2H])([2H])C(Cl)=O WETWJCDKMRHUPV-FIBGUPNXSA-N 0.000 description 1
- PPBRXRYQALVLMV-BVPCXHAQSA-N C(=C(C1=C(C(=CC=C1)[2H])[2H])[2H])([2H])[2H] Chemical compound C(=C(C1=C(C(=CC=C1)[2H])[2H])[2H])([2H])[2H] PPBRXRYQALVLMV-BVPCXHAQSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910010199 LiAl Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 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
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000012792 core layer Substances 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- PSGCRHLFZJRYEA-UHFFFAOYSA-N phosphorus p2o5 Chemical compound P.O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 PSGCRHLFZJRYEA-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005553 polystyrene-acrylate Polymers 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6371185A JPS61225143A (ja) | 1985-03-29 | 1985-03-29 | 弗素置換重水素化スチレン単量体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6371185A JPS61225143A (ja) | 1985-03-29 | 1985-03-29 | 弗素置換重水素化スチレン単量体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61225143A JPS61225143A (ja) | 1986-10-06 |
| JPH0125727B2 true JPH0125727B2 (US06362379-20020326-C00018.png) | 1989-05-19 |
Family
ID=13237231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6371185A Granted JPS61225143A (ja) | 1985-03-29 | 1985-03-29 | 弗素置換重水素化スチレン単量体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61225143A (US06362379-20020326-C00018.png) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102093540B1 (ko) * | 2017-08-11 | 2020-03-25 | 주식회사 엘지화학 | 할로겐 치환된 스티렌 모노머의 제조방법 |
-
1985
- 1985-03-29 JP JP6371185A patent/JPS61225143A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61225143A (ja) | 1986-10-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4349650A (en) | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom | |
| CN1125030C (zh) | 卤化丙烯酸酯及由其制得的聚合物 | |
| US4275225A (en) | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom | |
| US4273728A (en) | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom | |
| CA2356274A1 (en) | Polymerizable halogenated vinyl ethers | |
| JPS6345737B2 (US06362379-20020326-C00018.png) | ||
| KR100912325B1 (ko) | 퍼플루오로아다만틸 아크릴산 에스터류 및 그의 중간체 | |
| JP5028735B2 (ja) | 新規含フッ素化合物、その製造方法およびその重合体 | |
| US20050288528A1 (en) | Fluorinated adamantane and its derivatives | |
| US4292449A (en) | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom | |
| JPS63119434A (ja) | ３−ブロモ−４−フルオロ−ベンズアルデヒドアセタールおよびその製法 | |
| JP2001122828A (ja) | ２官能（メタ）アクリル酸エステル組成物とそのための２価アルコール | |
| JPH0125727B2 (US06362379-20020326-C00018.png) | ||
| JP2563959B2 (ja) | 含フッ素エーテル化合物及びその製造方法 | |
| JPS63130563A (ja) | （メタ）アクリル酸エステル | |
| KR20040047937A (ko) | 불소함유 디엔 화합물 및 불소함유 중합체와 그 제조 방법 | |
| US4578508A (en) | Fluoroacrylate ester, polymer thereof, and process of making the same | |
| Frost | Preparation and Properties of Some Negatively-substituted Organosilanes | |
| Hung et al. | The chemistry of fluorinated dioxoles and dioxolanes. 3. Fluorinated dioxolane olefins and epoxides | |
| JPH0772218B2 (ja) | α−フルオルアクリル酸エステルの弗素含有共重合体より成る有機光学材料 | |
| US5198925A (en) | α-fluoroacrylic acid esters and polymers thereof | |
| US4633023A (en) | Fluoroacrylate ester, polymer thereof, and process of making the same | |
| US5093512A (en) | Process for producing fluorinated organic compounds | |
| WO2002088058A1 (fr) | Procede de preparation d'alcools benzyliques | |
| US5171893A (en) | Process for producing fluorinated organic compounds |
