JPH0526803B2 - - Google Patents
Info
- Publication number
- JPH0526803B2 JPH0526803B2 JP13823584A JP13823584A JPH0526803B2 JP H0526803 B2 JPH0526803 B2 JP H0526803B2 JP 13823584 A JP13823584 A JP 13823584A JP 13823584 A JP13823584 A JP 13823584A JP H0526803 B2 JPH0526803 B2 JP H0526803B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- polymerization
- substituted
- polymer
- maleamic
- 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 - Lifetime
Links
- -1 N-substituted maleamic acid Chemical class 0.000 claims description 38
- 238000006116 polymerization reaction Methods 0.000 claims description 30
- 238000010438 heat treatment Methods 0.000 claims description 12
- 229920001971 elastomer Polymers 0.000 claims description 9
- 239000005060 rubber Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- 150000008360 acrylonitriles Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 23
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 125000004018 acid anhydride group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical class CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- HATJOEAOEPFQBK-XFXZXTDPSA-N (Z)-4-amino-2-(4-butylphenyl)-4-oxobut-2-enoic acid Chemical compound C(CCC)C1=CC=C(C=C1)/C(/C(=O)O)=C/C(=O)N HATJOEAOEPFQBK-XFXZXTDPSA-N 0.000 description 1
- HBQGCOWNLUOCBU-ONEGZZNKSA-N (e)-4-(ethylamino)-4-oxobut-2-enoic acid Chemical compound CCNC(=O)\C=C\C(O)=O HBQGCOWNLUOCBU-ONEGZZNKSA-N 0.000 description 1
- DFQUBYCHLQAFOW-NSCUHMNNSA-N (e)-4-(methylamino)-4-oxobut-2-enoic acid Chemical compound CNC(=O)\C=C\C(O)=O DFQUBYCHLQAFOW-NSCUHMNNSA-N 0.000 description 1
- RPHFOECPERWGCT-WAYWQWQTSA-N (z)-4-(4-cyanoanilino)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)NC1=CC=C(C#N)C=C1 RPHFOECPERWGCT-WAYWQWQTSA-N 0.000 description 1
- AZVWYXUTXSTOQY-WAYWQWQTSA-N (z)-4-(4-nitroanilino)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)NC1=CC=C([N+]([O-])=O)C=C1 AZVWYXUTXSTOQY-WAYWQWQTSA-N 0.000 description 1
- DEWAGGNAHQGYBD-SREVYHEPSA-N (z)-4-(cyclohexylamino)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)NC1CCCCC1 DEWAGGNAHQGYBD-SREVYHEPSA-N 0.000 description 1
- OEWYPDFKPCJYMS-SEYXRHQNSA-N (z)-4-(dodecylamino)-4-oxobut-2-enoic acid Chemical compound CCCCCCCCCCCCNC(=O)\C=C/C(O)=O OEWYPDFKPCJYMS-SEYXRHQNSA-N 0.000 description 1
- HXXJDJHHLXEVBZ-SREVYHEPSA-N (z)-4-(hexylamino)-4-oxobut-2-enoic acid Chemical compound CCCCCCNC(=O)\C=C/C(O)=O HXXJDJHHLXEVBZ-SREVYHEPSA-N 0.000 description 1
- PTDZPBBGCHHKCY-HJWRWDBZSA-N (z)-4-(octylamino)-4-oxobut-2-enoic acid Chemical compound CCCCCCCCNC(=O)\C=C/C(O)=O PTDZPBBGCHHKCY-HJWRWDBZSA-N 0.000 description 1
- QWBGMRIVKZHYFD-YVMONPNESA-N (z)-4-amino-2-(4-chlorophenyl)-4-oxobut-2-enoic acid Chemical compound NC(=O)\C=C(/C(O)=O)C1=CC=C(Cl)C=C1 QWBGMRIVKZHYFD-YVMONPNESA-N 0.000 description 1
- ZUQPOUDHEBAFSU-YVMONPNESA-N (z)-4-amino-2-(4-hydroxyphenyl)-4-oxobut-2-enoic acid Chemical compound NC(=O)\C=C(/C(O)=O)C1=CC=C(O)C=C1 ZUQPOUDHEBAFSU-YVMONPNESA-N 0.000 description 1
- XWMSUAPRMXCBDR-TWGQIWQCSA-N (z)-4-amino-2-(4-methylphenyl)-4-oxobut-2-enoic acid Chemical compound CC1=CC=C(C(=C\C(N)=O)\C(O)=O)C=C1 XWMSUAPRMXCBDR-TWGQIWQCSA-N 0.000 description 1
- PFADNFHOEAYBSZ-VURMDHGXSA-N (z)-4-amino-4-oxo-2-phenylbut-2-enoic acid Chemical compound NC(=O)\C=C(/C(O)=O)C1=CC=CC=C1 PFADNFHOEAYBSZ-VURMDHGXSA-N 0.000 description 1
- WHZLCOICKHIPRL-SREVYHEPSA-N (z)-4-anilino-4-oxobut-2-enoic acid Chemical class OC(=O)\C=C/C(=O)NC1=CC=CC=C1 WHZLCOICKHIPRL-SREVYHEPSA-N 0.000 description 1
- YSGGHSDBNZOIHX-KHPPLWFESA-N (z)-4-oxo-4-(4-phenoxyanilino)but-2-enoic acid Chemical compound C1=CC(NC(=O)\C=C/C(=O)O)=CC=C1OC1=CC=CC=C1 YSGGHSDBNZOIHX-KHPPLWFESA-N 0.000 description 1
- HPDQADRQTVTWTP-ARJAWSKDSA-N (z)-4-oxo-4-(propan-2-ylamino)but-2-enoic acid Chemical compound CC(C)NC(=O)\C=C/C(O)=O HPDQADRQTVTWTP-ARJAWSKDSA-N 0.000 description 1
- BJQFWAQRPATHTR-UHFFFAOYSA-N 1,2-dichloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1Cl BJQFWAQRPATHTR-UHFFFAOYSA-N 0.000 description 1
- XHAFIUUYXQFJEW-UHFFFAOYSA-N 1-chloroethenylbenzene Chemical compound ClC(=C)C1=CC=CC=C1 XHAFIUUYXQFJEW-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- XCAHQTQAKZJCJD-YVMONPNESA-N 4-[(z)-3-amino-1-carboxy-3-oxoprop-1-enyl]benzoic acid Chemical compound NC(=O)\C=C(/C(O)=O)C1=CC=C(C(O)=O)C=C1 XCAHQTQAKZJCJD-YVMONPNESA-N 0.000 description 1
- QBCNWCOWDJFGGY-TWGQIWQCSA-N COC1=CC=C(C=C1)/C(/C(=O)O)=C/C(=O)N Chemical compound COC1=CC=C(C=C1)/C(/C(=O)O)=C/C(=O)N QBCNWCOWDJFGGY-TWGQIWQCSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- RCFKIGITIBNPQE-UHFFFAOYSA-N methyl 2,2-difluoro-3-oxopentanoate Chemical compound CCC(=O)C(F)(F)C(=O)OC RCFKIGITIBNPQE-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 description 1
- 239000004331 potassium propionate Substances 0.000 description 1
- 235000010332 potassium propionate Nutrition 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13823584A JPS6116904A (ja) | 1984-07-03 | 1984-07-03 | マレイミド系重合体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13823584A JPS6116904A (ja) | 1984-07-03 | 1984-07-03 | マレイミド系重合体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6116904A JPS6116904A (ja) | 1986-01-24 |
| JPH0526803B2 true JPH0526803B2 (fr) | 1993-04-19 |
Family
ID=15217238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13823584A Granted JPS6116904A (ja) | 1984-07-03 | 1984-07-03 | マレイミド系重合体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6116904A (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5077343A (en) * | 1989-10-12 | 1991-12-31 | The Dow Chemical Company | Method for preparing imide-containing polymers |
| US5015712A (en) * | 1989-10-12 | 1991-05-14 | The Dow Chemical Company | Method for preparing imide-containing polymers |
| JPH03199214A (ja) * | 1989-12-27 | 1991-08-30 | Sumitomo Chem Co Ltd | 変性重合体ゴム及びその製造方法 |
-
1984
- 1984-07-03 JP JP13823584A patent/JPS6116904A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6116904A (ja) | 1986-01-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6126936B2 (fr) | ||
| GB2102815A (en) | Heat resistant resins | |
| JPH068374B2 (ja) | 熱可塑性樹脂組成物 | |
| JPS6045642B2 (ja) | 熱可塑性樹脂の製法 | |
| US4598126A (en) | Heat resistant resin composition | |
| JPS628456B2 (fr) | ||
| JP3471830B2 (ja) | ガラス繊維強化熱可塑性樹脂組成物 | |
| JPS6241974B2 (fr) | ||
| JPS58101141A (ja) | 熱可塑性樹脂組成物 | |
| JPH0526803B2 (fr) | ||
| US4451617A (en) | Miscible polyblend and molded article produced therefrom | |
| JPS6234785B2 (fr) | ||
| JPH0471403B2 (fr) | ||
| JPS60243102A (ja) | 熱可塑性樹脂の製造法 | |
| JPH0556364B2 (fr) | ||
| JPS6046122B2 (ja) | 熱可塑性重合体の製造方法 | |
| US20030236356A1 (en) | Safe process for making polymers containing n-phenylimide groups | |
| JP3138334B2 (ja) | マレイミド系耐熱性共重合体の製造方法 | |
| JPS6220549A (ja) | 耐変色性樹脂組成物 | |
| JPH06199938A (ja) | グルタルイミドコポリマーの製造方法と、その中間化合物 | |
| JPH0333722B2 (fr) | ||
| JPH0526820B2 (fr) | ||
| JPH031323B2 (fr) | ||
| JPH0262585B2 (fr) | ||
| JPS6238380B2 (fr) |