JPS623165B2 - - Google Patents
Info
- Publication number
- JPS623165B2 JPS623165B2 JP10648579A JP10648579A JPS623165B2 JP S623165 B2 JPS623165 B2 JP S623165B2 JP 10648579 A JP10648579 A JP 10648579A JP 10648579 A JP10648579 A JP 10648579A JP S623165 B2 JPS623165 B2 JP S623165B2
- Authority
- JP
- Japan
- Prior art keywords
- styrene
- maleic acid
- alkyl
- maleic
- substituted styrene
- 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 Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 55
- 150000003440 styrenes Chemical class 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000002689 maleic acids Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- DTCCVIYSGXONHU-CJHDCQNGSA-N (z)-2-(2-phenylethenyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\C=CC1=CC=CC=C1 DTCCVIYSGXONHU-CJHDCQNGSA-N 0.000 claims description 7
- 239000002685 polymerization catalyst Substances 0.000 claims description 4
- 238000010526 radical polymerization reaction Methods 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
- 239000011976 maleic acid Substances 0.000 description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 13
- 229920001519 homopolymer Polymers 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 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 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000005023 xylyl group Chemical group 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- -1 styrene compound Chemical class 0.000 description 2
- IQBLWPLYPNOTJC-FPLPWBNLSA-N (z)-4-(2-ethylhexoxy)-4-oxobut-2-enoic acid Chemical compound CCCCC(CC)COC(=O)\C=C/C(O)=O IQBLWPLYPNOTJC-FPLPWBNLSA-N 0.000 description 1
- AQGMJUDZABJUBH-UPHRSURJSA-N (z)-4-chloro-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(Cl)=O AQGMJUDZABJUBH-UPHRSURJSA-N 0.000 description 1
- ZMQWRASVUXJXGM-SREVYHEPSA-N (z)-4-cyclohexyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1CCCCC1 ZMQWRASVUXJXGM-SREVYHEPSA-N 0.000 description 1
- GPTNZCCQHNGXMS-SREVYHEPSA-N (z)-4-oxo-4-phenoxybut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1=CC=CC=C1 GPTNZCCQHNGXMS-SREVYHEPSA-N 0.000 description 1
- QKUGKZFASYQCGO-SREVYHEPSA-N (z)-4-oxo-4-phenylmethoxybut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OCC1=CC=CC=C1 QKUGKZFASYQCGO-SREVYHEPSA-N 0.000 description 1
- ZLYYJUJDFKGVKB-UPHRSURJSA-N (z)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C/C(Cl)=O ZLYYJUJDFKGVKB-UPHRSURJSA-N 0.000 description 1
- WQDGTJOEMPEHHL-UHFFFAOYSA-N 1-chloro-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(Cl)C=C1 WQDGTJOEMPEHHL-UHFFFAOYSA-N 0.000 description 1
- IHKJXCKVKGBGSQ-UHFFFAOYSA-N 1-tert-butyl-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(C(C)(C)C)C=C1 IHKJXCKVKGBGSQ-UHFFFAOYSA-N 0.000 description 1
- UGMAWHGKALHDPD-UHFFFAOYSA-N 3-benzylfuran-2,5-dione Chemical compound O=C1OC(=O)C(CC=2C=CC=CC=2)=C1 UGMAWHGKALHDPD-UHFFFAOYSA-N 0.000 description 1
- MLMKPOWLMMOBEY-UHFFFAOYSA-N 3-cyclohexylfuran-2,5-dione Chemical compound O=C1OC(=O)C(C2CCCCC2)=C1 MLMKPOWLMMOBEY-UHFFFAOYSA-N 0.000 description 1
- LPFJFXRQANKTRA-UHFFFAOYSA-N 3-propylfuran-2,5-dione Chemical compound CCCC1=CC(=O)OC1=O LPFJFXRQANKTRA-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10648579A JPS5630416A (en) | 1979-08-20 | 1979-08-20 | Preparation of styrene-maleic acid low polymer |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10648579A JPS5630416A (en) | 1979-08-20 | 1979-08-20 | Preparation of styrene-maleic acid low polymer |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5630416A JPS5630416A (en) | 1981-03-27 |
JPS623165B2 true JPS623165B2 (fr) | 1987-01-23 |
Family
ID=14434765
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10648579A Granted JPS5630416A (en) | 1979-08-20 | 1979-08-20 | Preparation of styrene-maleic acid low polymer |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5630416A (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01147970A (ja) * | 1987-12-04 | 1989-06-09 | Fuji Photo Optical Co Ltd | プロンプター |
JPH01276881A (ja) * | 1988-04-28 | 1989-11-07 | Asahi Glass Co Ltd | プロンプター及びその駆動方法 |
-
1979
- 1979-08-20 JP JP10648579A patent/JPS5630416A/ja active Granted
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01147970A (ja) * | 1987-12-04 | 1989-06-09 | Fuji Photo Optical Co Ltd | プロンプター |
JPH01276881A (ja) * | 1988-04-28 | 1989-11-07 | Asahi Glass Co Ltd | プロンプター及びその駆動方法 |
Also Published As
Publication number | Publication date |
---|---|
JPS5630416A (en) | 1981-03-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2004014926A2 (fr) | Alcoxyamines issues de nitroxydes βετα-phosphores, leur utilisation en polymerisation radicalaire | |
JP5709094B2 (ja) | アルケニルリン化合物、アルケニルリン化合物重合体、及びアルケニルリン化合物共重合体 | |
JP2002537304A (ja) | β亜燐酸ニトロキシドから得られるアルコキシアミン | |
JPS58167606A (ja) | ラジカル共重合によるグラフト共重合体の製造方法 | |
US2684379A (en) | Process for producing polysiloxanes | |
JP2614614B2 (ja) | 光学活性スチレン誘導体,それらの重合体、イリジウム(i)との錯塩及びこれらの利用 | |
JPS623165B2 (fr) | ||
US9879103B2 (en) | Initiation of controlled radical polymerization from lactide monomer | |
US2695307A (en) | Process of manufacturing polymerized organic silicon compounds | |
JPS63250388A (ja) | モノアルコキシシラン化合物の製造方法 | |
JPH0337206A (ja) | アクリル系単量体の塊状付加重合法 | |
TWI352083B (en) | Method for producing hexaalkylborzaine | |
JP3743687B2 (ja) | ハロゲン化アルキルを用いるテトラキス(ペンタフルオロフェニル)ボレート誘導体の製造方法 | |
JP5880907B2 (ja) | アルケニルリン化合物、アルケニルリン化合物重合体、及びアルケニルリン化合物共重合体 | |
JP5786269B2 (ja) | アルケニルリン化合物の製造方法、アルケニルリン化合物重合体の製造方法、及びアルケニルリン化合物共重合体の製造方法 | |
JPH055009A (ja) | ビニル系単量体の重合法 | |
BE1001232A3 (fr) | Copolymeres sequences radiaux et ramifies, compositions les contenant , leur preparation et leur utilisation dans des compositions bitumineuses. | |
US4814473A (en) | Process for producing 5-vinylbicyclo[2.2.1]heptyltrichlorosilane | |
JPS61123643A (ja) | 熱可塑性成形材料 | |
JPH06287256A (ja) | ブロック共重合体の取得法 | |
JP4190367B2 (ja) | B,b’,b”−トリクロロ−n,n’,n”−トリアルキルボラジンおよびヘキサアルキルボラジンの製造方法 | |
JPH04124191A (ja) | 有機ケイ素化合物 | |
JP2621706B2 (ja) | 架橋ポリシラン及びその製造方法 | |
JPS6151599B2 (fr) | ||
JP4947680B2 (ja) | 新規硬化性ポリアミド及び重合性組成物 |