CA1265294A - Imide polymers - Google Patents
Imide polymersInfo
- Publication number
- CA1265294A CA1265294A CA000515945A CA515945A CA1265294A CA 1265294 A CA1265294 A CA 1265294A CA 000515945 A CA000515945 A CA 000515945A CA 515945 A CA515945 A CA 515945A CA 1265294 A CA1265294 A CA 1265294A
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- acid
- imide
- anhydride
- blend
- 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 - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 150
- 150000003949 imides Chemical class 0.000 title claims abstract description 115
- 239000002253 acid Substances 0.000 claims abstract description 139
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 134
- 239000000203 mixture Substances 0.000 claims abstract description 97
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 65
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 28
- 229920001577 copolymer Polymers 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 229920001169 thermoplastic Polymers 0.000 claims description 24
- 239000004417 polycarbonate Substances 0.000 claims description 17
- 229920000515 polycarbonate Polymers 0.000 claims description 15
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002033 PVDF binder Substances 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 10
- 239000004793 Polystyrene Substances 0.000 claims description 9
- 150000002148 esters Chemical group 0.000 claims description 9
- 239000004797 high-impact polystyrene Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229920005669 high impact polystyrene Polymers 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 150000003141 primary amines Chemical class 0.000 claims description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000005033 polyvinylidene chloride Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 150000001408 amides Chemical group 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical group CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 3
- 230000004580 weight loss Effects 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004801 Chlorinated PVC Substances 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 229920001283 Polyalkylene terephthalate Polymers 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 claims description 2
- 150000003504 terephthalic acids Chemical class 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims 1
- 150000002531 isophthalic acids Chemical class 0.000 claims 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 238000002411 thermogravimetry Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 38
- 230000008569 process Effects 0.000 abstract description 16
- 239000012815 thermoplastic material Substances 0.000 abstract description 2
- 239000004642 Polyimide Substances 0.000 description 125
- 229920001721 polyimide Polymers 0.000 description 111
- 239000003795 chemical substances by application Substances 0.000 description 67
- -1 methacrylate ester Chemical class 0.000 description 61
- 238000006243 chemical reaction Methods 0.000 description 34
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 239000002904 solvent Substances 0.000 description 21
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 15
- 239000000306 component Substances 0.000 description 14
- 238000002156 mixing Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229920006385 Geon Polymers 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 229940102838 methylmethacrylate Drugs 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229920002959 polymer blend Polymers 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 239000004926 polymethyl methacrylate Substances 0.000 description 8
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229920006370 Kynar Polymers 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010924 continuous production Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 5
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000005060 rubber Substances 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 229930182556 Polyacetal Natural products 0.000 description 4
- 229920000265 Polyparaphenylene Polymers 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940093470 ethylene Drugs 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920002492 poly(sulfone) Polymers 0.000 description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 description 4
- 229920006324 polyoxymethylene Polymers 0.000 description 4
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 3
- 229920013683 Celanese Polymers 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 229920000299 Nylon 12 Polymers 0.000 description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 3
- 101150107341 RERE gene Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229940063557 methacrylate Drugs 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 229920001230 polyarylate Polymers 0.000 description 3
- 229920001601 polyetherimide Polymers 0.000 description 3
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 description 3
- 229920000131 polyvinylidene Polymers 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004609 Impact Modifier Substances 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229920000571 Nylon 11 Polymers 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004697 Polyetherimide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- UMMAVKBKCCDXHW-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane;1-methoxy-2-[2-(2-methoxyethoxy)ethoxy]ethane Chemical group COCCOCCOC.COCCOCCOCCOC UMMAVKBKCCDXHW-UHFFFAOYSA-N 0.000 description 1
- DJKAITATKHRILQ-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane;methylsulfinylmethane Chemical compound CS(C)=O.COCCOCCOC DJKAITATKHRILQ-UHFFFAOYSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- CWGSOQVETBJTME-UHFFFAOYSA-N 3-(2-phenylethenyl)pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=CC=2C=CC=CC=2)=C1 CWGSOQVETBJTME-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- FKAWETHEYBZGSR-UHFFFAOYSA-N 3-methylidenepyrrolidine-2,5-dione Chemical compound C=C1CC(=O)NC1=O FKAWETHEYBZGSR-UHFFFAOYSA-N 0.000 description 1
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- 101100481029 Arabidopsis thaliana TGA3 gene Proteins 0.000 description 1
- 229920001824 Barex® Polymers 0.000 description 1
- 101100326167 Caenorhabditis elegans blos-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 102100037709 Desmocollin-3 Human genes 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LRULVYSBRWUVGR-FCHUYYIVSA-N GSK2879552 Chemical compound C1=CC(C(=O)O)=CC=C1CN1CCC(CN[C@H]2[C@@H](C2)C=2C=CC=CC=2)CC1 LRULVYSBRWUVGR-FCHUYYIVSA-N 0.000 description 1
- 101000968042 Homo sapiens Desmocollin-2 Proteins 0.000 description 1
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- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical group O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
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- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical compound CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 239000004248 saffron Substances 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229920006259 thermoplastic polyimide Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical group OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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- 238000003466 welding Methods 0.000 description 1
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US770,034 | 1985-08-27 | ||
| US06/770,034 US4727117A (en) | 1985-08-27 | 1985-08-27 | Imide polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1265294A true CA1265294A (en) | 1990-01-30 |
Family
ID=25087269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000515945A Expired - Fee Related CA1265294A (en) | 1985-08-27 | 1986-08-14 | Imide polymers |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4727117A (enExample) |
| EP (1) | EP0216505B1 (enExample) |
| JP (3) | JPS6289705A (enExample) |
| KR (1) | KR940008989B1 (enExample) |
| AT (1) | ATE85980T1 (enExample) |
| AU (1) | AU593835B2 (enExample) |
| BR (1) | BR8604056A (enExample) |
| CA (1) | CA1265294A (enExample) |
| DE (1) | DE3687813T2 (enExample) |
| ES (1) | ES2001756A6 (enExample) |
| MX (1) | MX9304049A (enExample) |
| NO (1) | NO167155C (enExample) |
| NZ (1) | NZ217376A (enExample) |
| SG (1) | SG50193G (enExample) |
| ZA (1) | ZA866492B (enExample) |
Families Citing this family (101)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6245642A (ja) * | 1985-08-23 | 1987-02-27 | Mitsubishi Rayon Co Ltd | 強化樹脂組成物 |
| CA1279747C (en) * | 1986-01-23 | 1991-01-29 | Hisao Anzai | Methacrylate resin composition and process for its preparation |
| JPS6422903A (en) * | 1987-07-20 | 1989-01-25 | Mitsubishi Rayon Co | Production of methacrylimide group-containing polymer |
| JPS6475553A (en) * | 1987-09-18 | 1989-03-22 | Mitsubishi Rayon Co | Thermoplastic resin composition |
| JPH01284543A (ja) * | 1988-05-11 | 1989-11-15 | Mitsubishi Rayon Co Ltd | 熱可塑性樹脂組成物 |
| US4971847A (en) * | 1989-06-02 | 1990-11-20 | Rohm And Haas Company | Multilayered structures |
| JPH0241352A (ja) | 1988-07-29 | 1990-02-09 | Mitsubishi Rayon Co Ltd | 熱可塑性樹脂組成物 |
| USH1004H (en) * | 1988-08-04 | 1991-12-03 | Mitsubishi Rayon Company Limited | Thermoplastic resin composition |
| JPH02127455A (ja) * | 1988-11-07 | 1990-05-16 | Mitsubishi Rayon Co Ltd | 熱可塑性樹脂組成物 |
| USH1042H (en) * | 1988-11-07 | 1992-04-07 | Thermoplastic resin compositions | |
| JPH02142845A (ja) * | 1988-11-24 | 1990-05-31 | Sekisui Chem Co Ltd | 塩素化塩化ビニル樹脂組成物 |
| JPH02158614A (ja) * | 1988-12-13 | 1990-06-19 | Mitsubishi Rayon Co Ltd | メタクリルイミド含有樹脂重合体およびそれを含む熱可塑性樹脂組成物 |
| US5147930A (en) * | 1989-11-16 | 1992-09-15 | Rohm And Haas Company | Polymer blends with enhanced properties |
| JPH02178309A (ja) * | 1988-12-29 | 1990-07-11 | Mitsubishi Rayon Co Ltd | メタクリルイミド含有重合体 |
| CA2006641A1 (en) * | 1988-12-29 | 1990-06-29 | Sasaki Isao | Methacrylimide-containing polymer and resin composition containing said polymer |
| JPH02242806A (ja) * | 1988-12-29 | 1990-09-27 | Mitsubishi Rayon Co Ltd | メタクリルイミド含有重合体 |
| JPH02178308A (ja) * | 1988-12-29 | 1990-07-11 | Mitsubishi Rayon Co Ltd | メタクリルイミド含有重合体 |
| US5017411A (en) * | 1989-05-01 | 1991-05-21 | Aluminum Company Of America | Polymer blend comprising polycarbonate, acrylonitrile-methylacrylate copolymer, and imide-acrylate copolymer |
| CA2015331A1 (en) * | 1989-05-02 | 1990-11-02 | Leslie A. Cohen | Ultraviolet resistant glutarimide |
| US5084517A (en) * | 1989-07-17 | 1992-01-28 | Rohm And Haas Company | Graft copolymers and a process for their preparation |
| US5232985A (en) * | 1989-07-17 | 1993-08-03 | Rohm And Haas Company | Graft copolymers and a process for their preparation |
| JPH0386748A (ja) * | 1989-08-30 | 1991-04-11 | Kanegafuchi Chem Ind Co Ltd | 塩素化塩化ビニル系樹脂組成物 |
| US5208083A (en) * | 1989-11-16 | 1993-05-04 | Rohm And Haas Company | Polymer blends with enhanced properties |
| US5284917A (en) * | 1989-11-24 | 1994-02-08 | Mitsubishi Rayon Co., Ltd. | Thermoplastic resin composition |
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-
1985
- 1985-08-27 US US06/770,034 patent/US4727117A/en not_active Expired - Lifetime
-
1986
- 1986-08-14 CA CA000515945A patent/CA1265294A/en not_active Expired - Fee Related
- 1986-08-21 DE DE8686306474T patent/DE3687813T2/de not_active Expired - Fee Related
- 1986-08-21 AT AT86306474T patent/ATE85980T1/de not_active IP Right Cessation
- 1986-08-21 EP EP86306474A patent/EP0216505B1/en not_active Expired - Lifetime
- 1986-08-25 AU AU61803/86A patent/AU593835B2/en not_active Ceased
- 1986-08-26 ES ES868601353A patent/ES2001756A6/es not_active Expired
- 1986-08-26 BR BR8604056A patent/BR8604056A/pt not_active IP Right Cessation
- 1986-08-26 NO NO863409A patent/NO167155C/no unknown
- 1986-08-26 JP JP61199896A patent/JPS6289705A/ja active Granted
- 1986-08-27 KR KR1019860007124A patent/KR940008989B1/ko not_active Expired - Fee Related
- 1986-08-27 NZ NZ217376A patent/NZ217376A/en unknown
- 1986-08-27 ZA ZA866492A patent/ZA866492B/xx unknown
-
1987
- 1987-05-28 JP JP62133254A patent/JPS63178158A/ja active Granted
-
1993
- 1993-04-17 SG SG501/93A patent/SG50193G/en unknown
- 1993-07-06 MX MX9304049A patent/MX9304049A/es unknown
-
1996
- 1996-12-13 JP JP8352929A patent/JP2980565B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE85980T1 (de) | 1993-03-15 |
| JPS63178158A (ja) | 1988-07-22 |
| SG50193G (en) | 1993-07-09 |
| DE3687813D1 (de) | 1993-04-01 |
| NO167155B (no) | 1991-07-01 |
| EP0216505A3 (en) | 1989-07-19 |
| MX9304049A (es) | 1995-01-31 |
| NZ217376A (en) | 1990-04-26 |
| JP2980565B2 (ja) | 1999-11-22 |
| JPH0541643B2 (enExample) | 1993-06-24 |
| NO863409L (no) | 1987-06-15 |
| JPS6289705A (ja) | 1987-04-24 |
| KR870002178A (ko) | 1987-03-30 |
| AU593835B2 (en) | 1990-02-22 |
| JPH10158529A (ja) | 1998-06-16 |
| KR940008989B1 (ko) | 1994-09-28 |
| EP0216505B1 (en) | 1993-02-24 |
| BR8604056A (pt) | 1987-11-17 |
| AU6180386A (en) | 1987-03-05 |
| US4727117A (en) | 1988-02-23 |
| JPH0340063B2 (enExample) | 1991-06-17 |
| NO167155C (no) | 1991-10-09 |
| ES2001756A6 (es) | 1988-06-16 |
| DE3687813T2 (de) | 1993-08-05 |
| ZA866492B (en) | 1987-04-29 |
| NO863409D0 (no) | 1986-08-26 |
| EP0216505A2 (en) | 1987-04-01 |
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