CN1263524A - 芳香马来酰亚胺和其使用方法 - Google Patents
芳香马来酰亚胺和其使用方法 Download PDFInfo
- Publication number
- CN1263524A CN1263524A CN98807168A CN98807168A CN1263524A CN 1263524 A CN1263524 A CN 1263524A CN 98807168 A CN98807168 A CN 98807168A CN 98807168 A CN98807168 A CN 98807168A CN 1263524 A CN1263524 A CN 1263524A
- Authority
- CN
- China
- Prior art keywords
- maleimide
- alkyl group
- low alkyl
- phenyl
- hydrogen
- 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.)
- Pending
Links
- -1 Aromatic maleimides Chemical class 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000005855 radiation Effects 0.000 claims abstract description 14
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000003205 fragrance Substances 0.000 claims description 11
- 125000006850 spacer group Chemical group 0.000 claims description 8
- KOHAAQZNKXPOID-UHFFFAOYSA-N 1-(2-tert-butylphenyl)pyrrole-2,5-dione Chemical compound CC(C)(C)C1=CC=CC=C1N1C(=O)C=CC1=O KOHAAQZNKXPOID-UHFFFAOYSA-N 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 abstract 1
- 230000000977 initiatory effect Effects 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000003949 imides Chemical class 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- 239000012747 synergistic agent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 235000003642 hunger Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000003847 radiation curing Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- PVXVWWANJIWJOO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine Chemical compound CCNC(C)CC1=CC=C2OCOC2=C1 PVXVWWANJIWJOO-UHFFFAOYSA-N 0.000 description 1
- AAZGPNZTJLHQJM-UHFFFAOYSA-N 1-(2-iodophenyl)pyrrole-2,5-dione Chemical compound IC1=CC=CC=C1N1C(=O)C=CC1=O AAZGPNZTJLHQJM-UHFFFAOYSA-N 0.000 description 1
- RFSCHBMMSVGJAY-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]pyrrole-2,5-dione Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=O)C=CC1=O RFSCHBMMSVGJAY-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DVVXXHVHGGWWPE-UHFFFAOYSA-N 2-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC=C1C(O)=O DVVXXHVHGGWWPE-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- AEIOZWYBDBVCGW-UHFFFAOYSA-N 2-tert-butylaniline Chemical compound CC(C)(C)C1=CC=CC=C1N AEIOZWYBDBVCGW-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical group FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- QMMZSJPSPRTHGB-UHFFFAOYSA-N MDEA Natural products CC(C)CCCCC=CCC=CC(O)=O QMMZSJPSPRTHGB-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
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- 230000000996 additive effect Effects 0.000 description 1
- 125000005399 allylmethacrylate group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
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- 239000006210 lotion Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
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- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
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- 239000012452 mother liquor Substances 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical class C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
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Abstract
公开了芳香马来酰亚胺和其制备方法。含有本发明化合物的组合物的聚合可通过把组合物用辐射光辐射而激活。芳香马来酰亚胺和其制备方法。
Description
相关申请的交叉参考
本发明涉及1997,5,27日提交的同时待审的临时申请系列号60/047,729(该申请全文引入作为参考),并根据35 USC 119(e)以其申请日为优先权日。
发明领域
本发明涉及芳香马来酰亚胺和其使用方法。
发明背景
乙烯不饱合化合物如丙烯酸酯衍生物可通过在光引发体系的存在下暴露于辐射下,一般是紫外光下来进行聚合。一般地,光引发体系包括(1)暴露于辐射下可引发乙烯不饱合化合物聚合的化合物(“光引发剂”),和任选地(2)助引发剂或增效剂,即作为氢原子供体的分子。该助引发剂或增效剂一般是具有连接到邻接杂原子的碳原子上的不稳定氢的醇类、叔胺类或醚类。
可商购大量具有各种结构的光引发剂以用于不同的体系。然而,几乎所有的商购辐射固化方法需要把引发剂加入到配方中,但大部分没有消耗掉。使用常规光引发剂通常产生小分子的光副产物。存在残余的光活性化合物和可萃取物可引起制品物理性能的降低,如降低了耐晒牢度、脱色和降低了耐氧化性。另外,残余的光引发剂可从固化的制件中萃取出或浸出或迁移至制件的表面,这在很多应用中是不希望的。
日益严厉的的环境保护法规加速开发和使用含有很少或不含挥发性有机化合物(一般是溶剂)的配方。因此,使用接近于100%反应组分的配方是非常有意义的。
已提出用脂肪族马来酰亚胺通过氢夺取机理作为丙烯酸酯体系光聚合的光引发剂。然而,以前尝试提供通过氢夺取机理光引发的芳香马来酰亚胺化合物不是完全成功的。
发明概述
本发明涉及用于辐射固化可光聚合化合物的芳香马来酰亚胺。因为本发明的芳香马来酰亚胺可引发可辐射固化化合物的光聚合,故该芳香马来酰亚胺可代替常规的光引发剂。得到的可光聚合引发体系可通常称为“不含光引发剂的体系”。
与常规的光引发剂不同,实质上所有的芳香马来酰亚胺在引发和光聚合过程中消耗掉了。因此,本发明的芳香马来酰亚胺可消除固化产品中与残余光引发剂有关的问题,这些问题在用常规光引发剂是经常可发现的。本发明的芳香马来酰亚胺也可使对溶剂基体系的需求达到最小。
本发明的芳香马来酰亚胺可用作乙烯不饱和化合物,具体是丙烯酸酯衍生物的光聚合反应中的光引发剂。本发明的芳香马来酰亚胺也可用作共聚单体,与可聚合化合物如乙烯醚一起使用。
本发明的N-芳香马来酰亚胺是邻取代的(本文也称为“扭曲”的)N-芳香马来酰亚胺。与其它芳香马来酰亚胺不同,该酰亚胺环不在苯环的平面上。虽然不希望受本发明的任何解释的限制,但目前认为本发明化合物的空间取向至少对该扭曲芳香马来酰亚胺(相比于“非扭曲”芳香马来酰亚胺)引发光引发的可光聚合体系的光聚合能力有一部分贡献。
本发明的邻取代的N-芳香马来酰亚胺具有下式(I)的结构:其中:
R1选自CX3、COOR、COR、OR、CN、SR、N(R)2、R8、X和MI;
R2、R3、R4和R5独立选自H、CX3、COOR、COR、OR、CN、SR、N(R)2、R8、X和MI;
R6和R7独立选自H、低级烷基、优选CH3,和卤化物,优选氯化物;
X是卤化物,优选是F、Cl、Br或I;
R选自H、低级烷基、环烷基和芳基;
R8选自低级烷基、环烷基和芳基;或R8是间隔基,优选在2位上,连接式(I)的至少两个化合物以形成二或多官能马来酰亚胺,所说的间隔基选自:其中Y和Z每一个独立选自C2-C10亚烷基,m是1-10的整数,n是1010的整数;和
本发明还提供可光聚合的组合物,其包括上式(I)的化合物作为一个组分,也提供在光聚合体系中使用式(I)化合物的方法。
附图简述
现已介绍本发明的一些特点和优点,其它一些从下面的详细描述和附图可得知,其中:
图1和图2表示比较例的结果,其中本发明的举例化合物用来引发丙烯酸酯的聚合,并表示放热(图1和图2分别为mW/mg和mW/摩尔)相对光引发的光聚合时间的变化;和
图3和图4表示另一个对比例的结果,其中本发明的举例化合物用来引发丙烯酸酯的聚合,并表示放热(mW/mL)相对光引发的光聚合时间的变化。
发明详述
R1选自CX3、COOR、COR、OR、CN、SR、N(R)2、R8、X和MI;
R2、R3、R4和R5独立选自H、CX3、COOR、COR、OR、CN、SR、N(R)2、R8、X和MI;
R6和R7独立选自H、低级烷基、优选CH3,和卤化物,优选氯化物;
X是卤化物,优选是F、Cl、Br或I;
R选自H、低级烷基、环烷基和芳基;
R8选自低级烷基、环烷基和芳基;或R8是间隔基,优选在2位上,连接式(I)的至少两个化合物以形成二或多官能马来酰亚胺,所说的间隔基选自:和其中Y和Z每一个独立选自C2-C10亚烷基,m是1-10的整数,n是1-10的整数;和
在本发明的一个实施方案中,式(I)化合物包括其中R1是CX3,每一个R2、R3、R4、R5、R7是氢且R6是氢或低级烷基的化合物。在本发明的另一个实施方案中,式(I)化合物包括其中R1是低级烷基,每一个R2、R3、R4、R5、R7是氢且R6是氢或低级烷基的化合物。在本发明的再一个实施方案中,式(I)化合物包括其中R1是卤素,每一个R2、R3、R4、R5、R7是氢或CX3且R6是氢或低级烷基的化合物。
本文所用的术“低级烷基”指的是C1-C10直链或支链烷基,如甲基、乙基、丙基、异丙基、丁基、叔丁基、仲丁基、戍基、已基等。术语“环烷基”指的是C3-C10环烷基,任选地用低级烷基取代。术语“芳基”指的是C6-C10环芳基,如苯基、萘基等,任选地用低级烷基取代。
N-(2-吲哚-苯基)马来酰亚胺(Ie)
N-(2-溴-3,5-CF3-苯基)马来酰亚胺(If)
以及其类似物。
一般地,用本领域的现有技术,稍作修改可制备式(I)的马来酰亚胺。例如化合物可用两步法来合成,该法从适当的取代芳香胺与马来酸酐(或取代的马来酸酐,如甲基马来酸酐)在极性溶剂如二***中反应开始,以相近定量产率制备酰胺酸。然后从溶剂中回收酰胺酸并可从回收的产物中除去残余溶剂和水。
第二步骤是酸催化环闭合以形成酰亚胺。该反应通过把酰胺酸溶解在适当的溶剂如有机烃溶剂如甲苯、任选有少量助溶剂如二甲基亚砜(DMSO)中,加入催化量的浓硫酸,加热该混合物,优选至回流,并通过水/溶剂共沸物除去水。然后除去过量的溶剂并在溶剂中沉淀残余的酰亚胺浓溶液。然后收集酰亚胺并干燥除掉水和残余溶剂。第二步骤与可有近似定量的产率。
本发明还提供可光聚合组合物,其包括式(I)的芳香马来酰亚胺作为其组分,例如为光引发剂、共聚单体等。这里所用的、如本领域技术人员能理解的,术语“可光聚合组合物”指的是当暴露于辐射下硬化或固化的组合物。
一般地,本发明的组合物包括乙烯不饱和化合物,包括单体、低聚物、聚合物、预聚物、树脂性的材料,任选分散或溶解在适当的可与其共聚的溶剂中、以及其混合物,这些化合物当暴露于辐射源(如紫外或UV辐射、或在UV光谱外辐射)下是可光聚合的。如本领域技术人员能理解的,该光聚合化合物可是单官能或可以是每个分子有两个或多个端基可聚合的乙烯不饱合基团。
示例的光可聚合化合物或前体包括、但不限于:反应性乙烯单体,包括丙烯酸单体如丙烯酸和甲基丙烯酸、和它们的酰胺、酯、盐和相应的腈。适当的乙烯单体包括但不限于:丙烯酸甲酯、丙烯酸乙酯、丙烯酸叔丁酯、丙烯酸异辛酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸2-乙基己酯、丙烯酸丁酯、甲基丙烯酸异丁酯、相应的丙烯酸羟基酯,即丙烯酸羟乙基酯、丙烯酸羟丙基酯、甲基丙烯酸羟乙基已基酯,丙烯酸乙二醇酯类,即二甲基丙烯酸乙二醇酯、二甲基丙烯酸己二醇酯、丙烯酸烯丙酯类,即甲基丙烯酸烯丙酯、甲基丙烯酸二烯丙酯,丙烯酸环氧酯类,即甲基丙烯酸甘油酯,和丙烯酸氨基塑料酯类,即丙烯酸蜜胺。另外也包括其它单体,如乙烯乙酸酯、乙烯卤化物和亚乙烯基卤化物和酰胺类,即甲基丙烯酰胺、丙烯酰胺、二丙酮丙烯酰胺、乙烯和亚乙烯基酯、乙烯和亚乙烯基醚、乙烯和亚乙烯基酮、丁二烯、乙烯芳香化物,即苯乙烯、烷基苯乙烯、卤代苯乙烯、烷氧基苯乙烯、二乙烯基苯、乙烯基甲苯等。预聚物包括丙烯酸酯化的环氧化物、聚酯和聚氨酯,并一般与适当单体一起使用来控制粘度。可光聚合的化合物可聚合以形成均聚物或与其它各种单体共聚。
可光聚合的化合物在本发明的组合物中的量为约0-99.9%重量,优选约80-约99.9%重量,以该组合物的总重计。
式(I)的芳香马来酰亚胺可单独或以其混合物形式用作光聚合引发剂。在本发明中,式(I)的化合物在可光聚合的组合物中的量为当暴露于辐射下足以引发其聚合的量。该组合物可包括约0.1-约20重量份式(I)的化合物,以该可光聚合的化合物的总重计。
该芳香马来酰亚胺特别有利地用在“无光引发剂”的体系,其中芳香马来酰亚胺代替常规的光引发剂。虽然不希望受本发明任何解释的限制,但相信邻取代的芳香马来酰亚胺通过氢夺取机理引发聚合,类似于用脂族马来酰亚胺所观察的那样。然而这种光引发性是令人吃惊的,因为观察到各种芳香马来酰亚胺不引发光聚合。式(I)的芳香马来酰亚胺在供体或受体中也可用作光引发剂和/或共聚单体,在该体系中马来酰亚胺是受体的例子而乙烯基醚和乙烯基酰胺是供体的例子。另外,不希望受本发明任何解释的限制,但目前相信:当混合物受辐射并通过激发的N-芳基马来酰亚胺的氢夺取而发生引发时,通过电荷转移复合机理进行了光共聚合。
本发明的可光聚合组合物也可含有其它的常规试剂,如聚合抑制剂、填料、紫外吸收剂和有机过氧化物。也可包括助引发剂或增效剂(即作为氢原子供体或电子供体的分子)作为本发明组合物的一个组分,这样也是有利的。助引发剂或增效剂在本领域是已知的,并一般是具有连接到邻接杂原子的碳原子上的不稳定氢的醇类、叔胺类或醚类。这些助引发剂的量为约0.2-约25重量%,以该组合物的总重计。适当的化合物包括、但不限于:三乙醇胺、甲基-二乙醇胺、乙基-二乙醇胺和二甲基氨基苯甲酸的酯。也可使用其它已知的助引发剂和加速剂。这些化合物对初始光引发起作助引发或加速的作用并可增加光聚合过程的效率和速率。
可使用常规的工艺和设备把该可光聚合的组合物涂到或沉积到基材的表面上。该组合物可作为实质上连续的膜涂布。另外一种方法,可以不连续的图案涂布该组合物。根据所得的固化产品所需要的厚度,可改变沉积的组合物的厚度。
一般地,基材用未固化的可光聚合的组合物涂布并在以预定速率移动的传输带上于可商购的UV或激发灯下通过。待涂布的基材可以是,例如金属、木材、矿物、玻璃、纸、塑料、纤维、陶瓷等。
用在本发明的活性能量光束可是可见光或是紫外光或在其光谱中包括可见光和紫外光。可用本领域已知的任何工艺使用紫外光,即在200nm-450nm范围的紫外辐射,特别是用从氯化氙受激准分子灯(购自于FusionSystems)激发的308nm发射光来辐射组合物,或用紫外光谱以外的辐射来辐射组合物,来活化该聚合反应。辐射可以是天然或人工的、单色的或多色的、不连贯的或连贯的,并应有足够的强度以活化本发明的光引发剂,从而进行聚合。常规辐射源包括萤光灯、受激准分子灯、汞灯、金属添加剂和弧光灯。连贯的光源是强制的氮、氙、氩离子-和离子化的氖激光,其发射光落在或重叠在本发明的化合物的紫外光或可见光吸收带上。
该组合物可用在任何种类的本领域已知的光聚合的用途上,包括作为用于固体的粘合剂以得到油漆、清漆、瓷漆、有色喷漆、染剂或油墨性质的固化产品。该组合物特别适用于在印刷工艺中如平版印刷、丝网印刷等中制备可光聚合的表面涂料。
本发明通过下面非限制性实施例进行进一步说明。
实施例1
制备N-(2-CF3-苯基)马来酰亚胺(Ia)
把32.5g马来酸酐放入700mL二***中并让其溶解。向该搅拌的溶液中喷入41.48mL2-三氟甲基苯胺。该反应在室温下进行过夜并观察到灰白色沉淀。然后加热该搅料的溶液几小时并过滤,得到灰白色固体。把母液和洗液合并再次搅拌,并滤掉其它的产物。然后合并固含物并在真空下干燥。具体的产率为90-98%。
然后把44.8g马来酸放入带有100mL甲苯和25mL DMSO的三颈瓶中,并让其溶解。然后向搅拌的混合物中加入1.8mL浓硫酸,然后把该混合物加热至约130℃。让该反应混合物回流4小时或直到不再观察到共沸。接着通过真空蒸馏除去过量的甲苯。然后把该混合物加入到搅拌的蒸馏水中以沉淀酰亚胺并除去过量的DMSO。让含水悬浮液搅拌过夜、然后过滤。接着在真空下干燥该灰白色固体以除去水、DMSO和甲苯。产率一般为90-97%。
用在d6-DMSO的1H和13C NMR分析来自这两个步骤的产物。马来酸的特征在于靠近13-14ppm处的酸质子的宽峰、靠近10ppm处的酰胺质子的峰和靠近质谱中6.4ppm处的单烯质子的双峰。马来酸的特征也在于碳谱中两个羰基的靠近165ppm处的双峰。马来酰亚胺的特征在于没有酸和酰胺质子峰,单烯峰移到质谱中靠近7.6ppm处。碳谱中马来酰亚胺表现出靠近170ppm处的单羰基峰。
用加热速率为20℃/分的DSC测定N-(2-CF3-苯基)马来酰亚胺的熔点,发现为115.91℃(吸热峰的最大值)。也算出熔化热为71.62J/g。
实施例2
制备N-(2-叔丁基-苯基)马来酰亚胺(Ib)
如实施例1所述制备N-(2-叔丁基-苯基)马来酰亚胺,除了用2-叔-丁基-苯胺代替2-三氟甲基苯胺。用加热速率为20℃/分的DSC测定N-(2-叔丁基-苯基)马来酰亚胺的熔点,发现为99.64℃(吸热峰的最大值)。也算出熔化热为94.02J/g。
实施例3
制备N-(2-CF3-苯基)甲基马来酰亚胺(Ic)
如实施例1所述制备N-(2-CF3-苯基)甲基马来酰亚胺,除了用柠康酐代替马来酸酐。
实施例4
制备N-(2-吲哚-苯基)甲基马来酰亚胺(Ie)
如实施例1所述制备N-(2-吲哚-苯基)甲基马来酰亚胺,除了用2-吲哚苯胺代替2-三氟甲基苯胺。
实施例5
制备N-(2-溴-3,5-CF3-苯基)马来酰亚胺(If)
如实施例1所述制备N-(2-溴-3,5-CF3-苯基)马来酰亚胺,除了用2-溴-3,5-三氟甲基苯胺代替2-三氟甲基苯胺。
实施例6
使用芳香马来酰亚胺作为光引发剂
图1和图2表示比较例的结果,其中本发明的举例化合物用来引发丙烯酸酯的聚合,并表示放热(图1和图2分别为mW/mg和mW/摩尔)相对光引发的光聚合时间的变化。具体地,制备马来酰亚胺在新鲜PEG400二丙烯酸酯中的3.5%(重量)溶液(用400-600ppm MHQ来抑制)。PEG400指的是聚乙二醇,MHQ指的是甲基氢醌。PEG400二丙烯酸酯(PEG400 DA)购自于Aldrich Chemical Co.。比较N-(2-CF3-苯基)马来酰亚胺(2-cf3PMI)和N-(2-叔丁基-苯基)马来酰亚胺(2-t-buPMI),以及N-甲基马来酰亚胺(MMI)、N-(4-三氟甲基-苯基)马来酰亚胺(4-CF3PMI)、N-(4-氰基-苯基)马来酰亚胺(4-CNPMI)和N-苯基马来酰亚胺(PMI)。光聚合可在通过增加中等压力的汞灯和在样品盖上的石英窗而改性的Perkin-Elmer DSC-7上进行。在氮气净化5分钟后在样品灯强度为约28mW/cm2下进行聚合。放热曲线峰的最大值与聚合的最大速率成正比,并且到峰最大值的时间与引发反应的总效率相关。
可用两种方式来比较数据:引发剂生色团(马来酰亚胺)的重量百分效率和单位摩尔效率。4-CF3PMI、PMI和4-CNPMI溶液表示聚合效率低于净的PEG400DA(1mW/mg)。以重量百分数计,2-叔-buPMI仅比PEG400DA高效很少量,而2-cf3PMI比PEG400DA高效5倍。这可与比PEG400DA高效7.5倍的典型脂族马来酰亚胺MMI的效率相比。发现2-cf3PMI的到峰最大值的时间稍短于MMI的。然而,当把数据规格化为引发剂生色团(马来酰亚胺)的单位摩尔效率时,发现2-cf3PMI比MMI高效约1.5倍且其的引发效率应与更具反应性的脂族马来酰亚胺相当。如上所述,样品的DSC曲线在图1和2中示出。
图3和4表示另外一个比较例的结果,其中本发明的举例化合物用来引发丙烯酸酯的聚合,并示出放热(mW/mL)相对于光引发光聚合时间的关系。制备上述的马来酰亚胺在新鲜PEG400DA中溶液。2-BR35CF3PM和2IPMI分别指N-(2-溴-3,5-三氟甲基-苯基)马来酰亚胺和N-(2-碘-苯基)马来酰亚胺。2-CF3PMI、MMI和4-CF3PMI的含义同上。如上进行光聚合反应,除了在样品上灯的光强度为约31mW/cm2。
图3把观察到的“扭曲”芳香马来酰亚胺的放热曲线和烷基马来酰亚胺MMI和非扭曲状芳香马来酰亚胺(4CF3PMI)的放热曲线进行比较。如图所示,非扭曲芳香马来酰亚胺4CF3PMI不引发聚合。2BR35CF3PMI和2IPMI显示出甚至与MMI相比有提高的反应性。图4比较了上述马来酰亚胺和常规引发剂体系(具有1%重量的胺(MDEA)的3%重量二苯酮(BP))的聚合效率。如图4所示,在这些条件下,2BR35CF3PMI和2IPMI比带有胺的二苯酮引发更有效。
综上,说明了用邻取代的(“扭曲”)芳香马来酰亚胺来引发PEG400DA二丙烯酸酯的聚合。具体地,2-CF3PMI表示出高于MMI的单位摩尔马来酰亚胺的引发效率,2BR35CF3PMI和2IPMI显示出与脂族马来酰亚胺MMI和常规二苯酮/胺体系相比提高的效率。
虽然不希望受本发明任何解释的限制,但相信造成这样的结果有两个方面:使酰亚胺环不和苯环在一个平面上的立体效应,以及取代基的排电子性能(electron withdrawing nature)。
对几个扭曲芳香马来酰亚胺晶体样品进行单晶X-射线衍射试验以测定邻取代的芳香马来酰亚胺的苯环与马来酰亚胺环的立体关系。这些试验确认了本发明马来酰亚胺的“扭曲”构型,即苯环和马来酰亚胺环不在一个平面上。根椐化合物的种类,这两个环的扭转角为约88-93度。
上述实施例举例说明本发明,但不想对本发明进行限制。
Claims (17)
2.权利要求1的化合物,其中R1是CX3,每一个R2、R3、R4、R5、R7是氢,且R6是氢或低级烷基。
3.权利要求1的化合物,其中R1是低级烷基,每一个R2、R3、R4、R5、R7是氢且R6是氢或低级烷基。
4.权利要求1的化合物,其中R1是卤素,每一个R2、R3、R4、R5、R7是氢或CX3且R6是氢或低级烷基。
5.权利要求1的化合物,其中所述化合物选自N-(2-CF3-苯基)马来酰亚胺、N-(2-叔-丁基苯基)马来酰亚胺、N-(2-CF3-甲基苯基)马来酰亚胺、N-(2,4,6-异丙基-3-马来酰亚胺-苯基)马来酰亚胺、N-(2-吲哚-苯基)马来酰亚胺、N-(2-溴-3,5-CF3-苯基)马来酰亚胺。
6.一种可光聚合的组合物,包括含至少一种乙烯不饱和双键的可光聚合化合物和含邻取代的N-芳香马来酰亚胺的光引发剂。
R1选自CX3、COOR、COR、OR、CN、SR、N(R)2、R8、X和MI;
R2、R3、R4和R5独立选自H、CX3、COOR、COR、OR、CN、SR、N(R)2、R8、X和MI;
R6和R7独立选自H、低级烷基和卤化物;
X是卤化物;
R选自H、低级烷基、环烷基和芳基;
R8选自低级烷基、环烷基和芳基;或R8是间隔基,优选在2位上,连接式(I)的至少两个化合物以形成二或多官能马来酰亚胺,所说的间隔基选自:其中Y和Z每一个独立选自C2-C10亚烷基,m是1-10的整数,n是1-10的整数;和
MI是其中R6和R7定义如上。
8.权利要求7的组合物,其中R1是CX3,每一个R2、R3、R4、R5、R7是氢且R6是氢或低级烷基。
9.权利要求7的组合物,其中R1是低级烷基,每一个R2、R3、R4、R5、R7是氢且R6是氢或低级烷基。
10.权利要求7的组合物,其中R1是卤素,每一个R2、R3、R4、R5、R7是氢或CX3且R6是氢或低级烷基。
11.权利要求7的组合物,其中所述化合物选自N-(2-CF3-苯基)马来酰亚胺、N-(2-叔-丁基苯基)马来酰亚胺、N-(2-CF3-甲基苯基)马来酰亚胺、N-(2,4,6-异丙基-3-马来酰亚胺-苯基)马来酰亚胺、N-(2-吲哚-苯基)马来酰亚胺、N-(2-溴-3,5-CF3-苯基)马来酰亚胺。
12.一种含至少一种乙烯不饱和双键的可光聚合化合物的聚合方法,包括在含有邻取代的N-芳香马来酰亚胺的光引发剂存在下、把所说的化合物暴露于辐射下。
R1选自CX3、COOR、COR、OR、CN、SR、N(R)2、R8、X和MI;
R2、R3、R4和R5独立选自H、CX3、COOR、COR、OR、CN、SR、N(R)2、R8、X和MI;
R6和R7独立选自H、低级烷基和卤化物;
X是卤化物;
R选自H、低级烷基、环烷基和芳基;
R8选自低级烷基、环烷基和芳基;或R8是间隔基,优选在2位上,连接式(I)的至少两个化合物以形成二或多官能马来酰亚胺,所说的间隔基选自:其中Y和Z每一个独立选自C2-C10亚烷基,m是1-10的整数,n是1-10的整数;和
14.权利要求13的方法,其中R1是CX3,每一个R2、R3、R4、R5、R7是氢且R6是氢或低级烷基。
15.权利要求13的方法,其中R1是低级烷基,每一个R2、R3、R4、R5、R7是氢且R6是氢或低级烷基。
16.权利要求13的方法,其中R1是卤素,每一个R2、R3、R4、R5、R7是氢或CX3且R6是氢或低级烷基。
17.权利要求13的方法,其中所述化合物选自N-(2-CF3-苯基)马来酰亚胺、N-(2-叔-丁基苯基)马来酰亚胺、N-(2-CF3-甲基苯基)马来酰亚胺、N-(2,4,6-异丙基-3-马来酰亚胺-苯基)马来酰亚胺、N-(2-吲哚-苯基)马来酰亚胺、N-(2-溴-3,5-CF3-苯基)马来酰亚胺。
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JPH0384016A (ja) * | 1989-08-28 | 1991-04-09 | Showa Highpolymer Co Ltd | 光硬化可能な組成物 |
US5196550A (en) * | 1990-04-30 | 1993-03-23 | The B. F. Goodrich Company | Maleimido group containing monomers |
JP3008475B2 (ja) * | 1990-10-24 | 2000-02-14 | 大日本インキ化学工業株式会社 | 光ファイバ被覆用紫外線硬化型樹脂組成物 |
US5446073A (en) * | 1993-03-31 | 1995-08-29 | Fusion Systems Corporation | Photopolymerization process employing a charge transfer complex without a photoinitiator |
US6025409A (en) * | 1996-02-29 | 2000-02-15 | Dsm N.V. | Radiation curable coating composition |
US6034150A (en) * | 1996-08-23 | 2000-03-07 | University Of Southern Mississippi | Polymerization processes using aliphatic maleimides |
-
1998
- 1998-05-26 JP JP50080499A patent/JP2002500670A/ja not_active Ceased
- 1998-05-26 AT AT98923758T patent/ATE288894T1/de not_active IP Right Cessation
- 1998-05-26 KR KR1019997010964A patent/KR20010012992A/ko not_active Application Discontinuation
- 1998-05-26 EP EP98923758A patent/EP0984931B1/en not_active Expired - Lifetime
- 1998-05-26 BR BR9809495-5A patent/BR9809495A/pt not_active IP Right Cessation
- 1998-05-26 US US09/084,519 patent/US6153662A/en not_active Expired - Fee Related
- 1998-05-26 AU AU75975/98A patent/AU7597598A/en not_active Abandoned
- 1998-05-26 WO PCT/US1998/010655 patent/WO1998054134A1/en active IP Right Grant
- 1998-05-26 DE DE69828964T patent/DE69828964T2/de not_active Expired - Fee Related
- 1998-05-26 CN CN98807168A patent/CN1263524A/zh active Pending
- 1998-05-26 CA CA002290737A patent/CA2290737A1/en not_active Abandoned
-
1999
- 1999-04-29 US US09/302,081 patent/US6150431A/en not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102492320A (zh) * | 2011-12-05 | 2012-06-13 | 北方涂料工业研究设计院 | 耐高温光纤用快速固化聚酰亚胺涂料 |
CN102492320B (zh) * | 2011-12-05 | 2014-01-15 | 中昊北方涂料工业研究设计院有限公司 | 耐高温光纤用快速固化聚酰亚胺涂料 |
CN113582905A (zh) * | 2021-09-06 | 2021-11-02 | 福建师范大学泉港石化研究院 | 一种酰亚胺类衍生物及其制备方法 |
CN113582905B (zh) * | 2021-09-06 | 2022-12-09 | 福建师范大学泉港石化研究院 | 一种酰亚胺类衍生物及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
EP0984931A1 (en) | 2000-03-15 |
WO1998054134A1 (en) | 1998-12-03 |
KR20010012992A (ko) | 2001-02-26 |
DE69828964T2 (de) | 2006-03-30 |
US6150431A (en) | 2000-11-21 |
ATE288894T1 (de) | 2005-02-15 |
EP0984931B1 (en) | 2005-02-09 |
AU7597598A (en) | 1998-12-30 |
DE69828964D1 (de) | 2005-03-17 |
US6153662A (en) | 2000-11-28 |
JP2002500670A (ja) | 2002-01-08 |
CA2290737A1 (en) | 1998-12-03 |
BR9809495A (pt) | 2000-10-17 |
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