JPH0556364B2 - - Google Patents
Info
- Publication number
- JPH0556364B2 JPH0556364B2 JP17426584A JP17426584A JPH0556364B2 JP H0556364 B2 JPH0556364 B2 JP H0556364B2 JP 17426584 A JP17426584 A JP 17426584A JP 17426584 A JP17426584 A JP 17426584A JP H0556364 B2 JPH0556364 B2 JP H0556364B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- polymerization
- substituted
- maleamic
- copolymer
- 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 44
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 33
- 229920001577 copolymer Polymers 0.000 claims description 19
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 229920001971 elastomer Polymers 0.000 claims description 5
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 claims description 5
- 239000005060 rubber Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- 239000002253 acid Substances 0.000 description 9
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000001632 sodium acetate Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010556 emulsion polymerization method Methods 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 150000008360 acrylonitriles Chemical class 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- IZMZREOTRMMCCB-UHFFFAOYSA-N 1,4-dichloro-2-ethenylbenzene Chemical compound ClC1=CC=C(Cl)C(C=C)=C1 IZMZREOTRMMCCB-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-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
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-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
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- 229920006235 chlorinated polyethylene elastomer Polymers 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 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
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 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
- 230000035484 reaction time Effects 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
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17426584A JPS6153306A (ja) | 1984-08-22 | 1984-08-22 | マレイミド系共重合体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17426584A JPS6153306A (ja) | 1984-08-22 | 1984-08-22 | マレイミド系共重合体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6153306A JPS6153306A (ja) | 1986-03-17 |
| JPH0556364B2 true JPH0556364B2 (fr) | 1993-08-19 |
Family
ID=15975617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17426584A Granted JPS6153306A (ja) | 1984-08-22 | 1984-08-22 | マレイミド系共重合体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6153306A (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5123227A (en) * | 1988-04-21 | 1992-06-23 | Snow Brand Milk Products Co., Ltd. | Positioning and press-sealing means |
| US5015712A (en) * | 1989-10-12 | 1991-05-14 | The Dow Chemical Company | Method for preparing imide-containing polymers |
-
1984
- 1984-08-22 JP JP17426584A patent/JPS6153306A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6153306A (ja) | 1986-03-17 |
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