JP5577595B2 - ポリアミドの製造方法および樹脂組成物 - Google Patents
ポリアミドの製造方法および樹脂組成物 Download PDFInfo
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- JP5577595B2 JP5577595B2 JP2008543600A JP2008543600A JP5577595B2 JP 5577595 B2 JP5577595 B2 JP 5577595B2 JP 2008543600 A JP2008543600 A JP 2008543600A JP 2008543600 A JP2008543600 A JP 2008543600A JP 5577595 B2 JP5577595 B2 JP 5577595B2
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- 125000000962 organic group Chemical group 0.000 claims description 20
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
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- FNZBSNUICNVAAM-UHFFFAOYSA-N trimethyl-[methyl-[methyl-(methyl-phenyl-trimethylsilyloxysilyl)oxy-phenylsilyl]oxy-phenylsilyl]oxysilane Chemical compound C=1C=CC=CC=1[Si](C)(O[Si](C)(C)C)O[Si](C)(C=1C=CC=CC=1)O[Si](C)(O[Si](C)(C)C)C1=CC=CC=C1 FNZBSNUICNVAAM-UHFFFAOYSA-N 0.000 description 3
- LAGVOJJKZPIRMS-UHFFFAOYSA-N (1,2,2,6,6-pentamethylpiperidin-3-yl) 2-methylprop-2-enoate Chemical compound CN1C(C)(C)CCC(OC(=O)C(C)=C)C1(C)C LAGVOJJKZPIRMS-UHFFFAOYSA-N 0.000 description 2
- AJOJTMNIQSTBAP-UHFFFAOYSA-N (1,2,2,6,6-pentamethylpiperidin-3-yl) prop-2-enoate Chemical compound CN1C(C)(C)CCC(OC(=O)C=C)C1(C)C AJOJTMNIQSTBAP-UHFFFAOYSA-N 0.000 description 2
- SEOSQBZZSQXYDO-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-1-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ON1C(C)(C)CCCC1(C)C SEOSQBZZSQXYDO-UHFFFAOYSA-N 0.000 description 2
- GIIUJJXXMYYQQD-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-1-yl) prop-2-enoate Chemical compound CC1(C)CCCC(C)(C)N1OC(=O)C=C GIIUJJXXMYYQQD-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- YJVIKVWFGPLAFS-UHFFFAOYSA-N 9-(2-methylprop-2-enoyloxy)nonyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCOC(=O)C(C)=C YJVIKVWFGPLAFS-UHFFFAOYSA-N 0.000 description 2
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- 239000002841 Lewis acid Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- GOLSFPMYASLXJC-UHFFFAOYSA-N 2-(dimethylamino)ethyl acetate Chemical compound CN(C)CCOC(C)=O GOLSFPMYASLXJC-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
- KSJPKJBQXJQMTK-UHFFFAOYSA-N 3-[1-(2-carboxyethenyl)cyclodecyl]prop-2-enoic acid Chemical compound OC(=O)C=CC1(C=CC(O)=O)CCCCCCCCC1 KSJPKJBQXJQMTK-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- QDBOAKPEXMMQFO-UHFFFAOYSA-N 4-(4-carbonochloridoylphenyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=C(C(Cl)=O)C=C1 QDBOAKPEXMMQFO-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-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
- OLIGPHACAFRDEN-UHFFFAOYSA-N 4-naphthoquinonediazidesulfonyl group Chemical group [N-]=[N+]=C1C=C(C2=C(C=CC=C2)C1=O)S(=O)=O OLIGPHACAFRDEN-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- KHLBYJOGKPIERQ-UHFFFAOYSA-N 5-naphthoquinonediazidesulfonyl group Chemical group [N-]=[N+]=C1C=CC2=C(C=CC=C2S(=O)=O)C1=O KHLBYJOGKPIERQ-UHFFFAOYSA-N 0.000 description 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- KNOXZDJKCBWKIL-UHFFFAOYSA-N Nc(cc1)cc(-c(cc(cc2)N)c2O)c1O Chemical compound Nc(cc1)cc(-c(cc(cc2)N)c2O)c1O KNOXZDJKCBWKIL-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- SJSFUXCZXODYAA-UHFFFAOYSA-N O=C(c(cc1)ccc1S(c(cc1)ccc1C([n]1cncc1)=O)(=O)=O)[n]1cncc1 Chemical compound O=C(c(cc1)ccc1S(c(cc1)ccc1C([n]1cncc1)=O)(=O)=O)[n]1cncc1 SJSFUXCZXODYAA-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-N 0.000 description 1
- GCNKJQRMNYNDBI-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(2-methylprop-2-enoyloxymethyl)butyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CC)COC(=O)C(C)=C GCNKJQRMNYNDBI-UHFFFAOYSA-N 0.000 description 1
- TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 description 1
- OQHMGFSAURFQAF-UHFFFAOYSA-N [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC(=O)C(C)=C OQHMGFSAURFQAF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000012490 blank solution Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229940091853 isobornyl acrylate Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003456 sulfonamides Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino-carboxylic acids or of polyamines and polycarboxylic acids
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyamides (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Materials For Photolithography (AREA)
Description
ポリマーを0.1重量%の濃度でN−メチル−2−ピロリドン(NMP)に溶解させた。この溶液について、下記条件のゲルパーミエーションクロマトグラフ(GPC)法によって重量平均分子量(Mw)の測定を行った。Mwについては10,000以上を合格、それ未満を不合格とした。また、分子量が5000未満の領域に着目し、残留有機不純物に由来する低分子ピークの有無を評価した。低分子ピークについては「なし」を合格、「あり」を不合格とした。
<GPC測定系>
検出器:Waters 996
システムコントローラー:Waters 2690
カラムオーブン:Waters HTR−B
サーモコントローラー:Waters TCM
カラム:TOSOH TSK guard column
TOSOH TSK−GEL α−4000
TOSOH TSK−GEL α−2500 。
ポリマー1gをポリエチレン瓶にとり、超純水100cm3を加えて室温で36時間静置し、イオン成分を抽出した。これをディスクフィルター(ミリポア製0.45μm PVDF)でろ過した。抽出液について、下記条件のイオンクロマトグラフ分析法によって塩素成分の分析を行い、試料からの抽出量を求めた。試料を用いずに同様の操作を行いブランク溶液とした。このとき塩素成分の濃度が5ppm以下を合格、それより多い場合を不合格とした。
<イオンクロマトグラフィ測定条件>
装置:Dionex社製 DX−500
試料注入量:0.5mL
溶離液:2mM−NaHCO3
分離カラム:4mmφ×250mm Ion Pac AS4A−SC
検出器:電気伝導度計 。
窒素気流下、250mlの三頸フラスコ中にイミダゾール27.2g(0.4モル)を入れ、NMP100gに室温で攪拌溶解させた。これを−5℃以下に冷却し、イソフタル酸クロリド20.3g(0.1モル)を100gのNMPに溶解させた液体を、反応溶液の温度が0℃を越えないようにして1時間かけて滴下した。滴下後、室温にて反応溶液をさらに3時間攪拌し、1Lの純水に投入して沈殿物を濾過した。濾過した沈殿物を純水で数回洗浄し、50℃の真空オーブンで100時間乾燥して、下記式(6)で示されるジイミダゾリド化合物Aを得た。
窒素気流下、250mlの三頸フラスコ中にイミダゾール27.2g(0.4モル)を入れ、塩化メチレン100gを入れて室温で攪拌した。これを−5℃以下に冷却し、4,4’−ジフェニルエーテルジカルボン酸ジクロリド29.5g(0.1モル)を100gの塩化メチレンに分散させた液体を、反応溶液の温度が0℃を越えないようにして1時間かけて滴下した。滴下後、室温にて反応溶液をさらに3時間攪拌し、反応中に生じた沈殿物を濾過した。濾過した沈殿物を純水で数回洗浄し、50℃の真空オーブンで100時間乾燥して、下記式(7)で示されるジイミダゾリド化合物Bを得た。
4,4’−ジフェニルエーテルジカルボン酸ジクロリド29.5g(0.1モル)を4,4’−ジフェニルスルホンジカルボン酸ジクロリド34.3g(0.1モル)にした以外は合成例2と同様にして、下記式(8)で示されるジイミダゾリド化合物Cを得た。
4,4’−ジフェニルエーテルジカルボン酸ジクロリド29.5g(0.1モル)を4,4’−ビフェニルジカルボン酸ジクロリド27.9g(0.1モル)にした以外は合成例2と同様にして、下記式(9)で示されるジイミダゾリド化合物Dを得た。
窒素気流下500mLの三頸フラスコ中に下記(10)で示されるジアミン36.6g(0.1モル)およびNMP300gを入れ、室温で攪拌溶解させた。その後、合成例1で得られたジイミダゾリド化合物A23.9g(0.09モル)を室温で添加した。この混合物を40℃で1時間、さらに50℃で10時間攪拌した。さらに、この溶液にシス−5−ノルボルネン−エンド−2,3−ジカルボン酸無水物3.28g(0.02モル)を添加し、50℃のままさらに10時間攪拌した。反応終了後、溶液を室温まで冷却し、5Lの純水に投入した。沈澱したポリマーを濾別し、5Lの純水に再分散後濾過する工程を3回繰り返した。最終的に濾別したポリマーを50℃で3日間真空乾燥し、ポリマーEを得た。
ジイミダゾリド化合物A23.9g(0.09モル)の代わりに、合成例2で得られたジイミダゾリド化合物B32.2g(0.09モル)を用いた以外は実施例1と同様にしてポリマーFを得た。
ジイミダゾリド化合物A23.9g(0.09モル)の代わりに、合成例3で得られたジイミダゾリド化合物C36.5g(0.09モル)を用いた以外は実施例1と同様にしてポリマーGを得た。
ジイミダゾリド化合物A23.9g(0.09モル)の代わりに、合成例4で得られたジイミダゾリド化合物D30.8g(0.09モル)を用いた以外は実施例1と同様にしてポリマーHを得た。
窒素気流下500mLの三頸フラスコ中に下記式(11)で示されるジアミン21.6g(0.1モル)およびNMP300gを入れ、室温で攪拌溶解させた。その後、合成例2で得られたジイミダゾリド化合物B32.2g(0.09モル)を室温で添加した。この混合物を40℃で1時間、さらに50℃で10時間攪拌した。さらに、この溶液にシス−5−ノルボルネン−エンド−2,3−ジカルボン酸無水物3.28g(0.02モル)を添加し、50℃のままさらに10時間攪拌した。反応終了後、溶液を室温まで冷却し、5Lの純水に投入した。沈澱したポリマーを濾別し、5Lの純水に再分散後濾過する工程を3回繰り返した。最終的に濾別したポリマーを50℃で3日間真空乾燥し、ポリマーIを得た。
前記式(11)で示されるジアミン21.6g(0.1モル)の代わりに、下記式(12)で示されるジアミン28.0g(0.1モル)を用いた以外は実施例5と同様にしてポリマーJを得た。
前記式(11)で示されるジアミン21.6g(0.1モル)の代わりに、下記式(13)で示されるジアミン23.2g(0.1モル)を用いた以外は実施例5と同様にしてポリマーKを得た。
前記式(11)で示されるジアミン21.6g(0.1モル)の代わりに、下記式(14)で示されるジアミン38.0g(0.1モル)を用いた以外は実施例5と同様にしてポリマーLを得た。
前記式(11)で示されるジアミン21.6g(0.1モル)の代わりに、4,4’−ジアミノジフェニルエーテル20.0g(0.1モル)を用いた以外は実施例5と同様にしてポリマーMを得た。
前記式(11)で示されるジアミン21.6g(0.1モル)の代わりに、下記式(15)で示されるジアミン12.4g(0.1モル)を用いた以外は実施例5と同様にしてポリマーNを得た。
前記式(11)で示されるジアミン21.6g(0.1モル)の代わりに、下記式(16)で示されるジアミン21.6g(0.1モル)を用いた以外は実施例5と同様にしてポリマーOを得た。
窒素気流下、1000mlの三頸フラスコ中に40.0gのイソフタル酸および1−ヒドロキシベンゾトリアゾールからなるジエステル(0.1モル)、前記式(10)で示されるジアミン36.6g(0.1モル)およびNMP500gを入れ、その後攪拌しながら75℃に加熱した。その際得られる溶液に1.27gの乾燥ピリジン(16mモル)をNMP10mlに溶かして徐々に滴下し、さらにこの溶液を75℃で24時間攪拌した。室温に冷却後、得られた清澄な黄色の反応溶液を濾過し、水3容量部に対してイソプロパノール1容量部からなる混合物400mlに加えた。沈澱した白色のポリマーを濾別し、水200mlで2回洗浄した。その後、50℃の温度で3日間真空乾燥し、ポリマーPを得た。
窒素気流下、250mlの三頸フラスコ中に前記式(10)で示されるジアミン36.6g(0.1モル)およびNMP500gを入れ、攪拌溶解させた。これを−5℃以下に冷却し、4,4’−ジフェニルエーテルジカルボン酸クロリド29.5g(0.1モル)を100gのNMPに溶解させた液体を、反応溶液の温度が0℃を越えないようにして1時間かけて滴下した。滴下後、室温にて反応溶液をさらに3時間攪拌し、1Lの純水に投入して沈殿物を濾過した。濾過した沈殿物を純水で数回洗浄し、50℃の温度で3日間真空乾燥し、ポリマーQを得た。
キノンジアジド化合物(a)の合成
乾燥窒素気流下、TrisP−HAP(商品名、本州化学工業(株)製)、15.3g(0.05モル)と5−ナフトキノンジアジドスルホニル酸クロリド40.3g(0.15モル)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合させたトリエチルアミン15.2gを系内が35℃以上にならないように滴下した。滴下後、応溶液を30℃で2時間攪拌した。トリエチルアミン塩を濾過して除き、濾液を水に投入した。その後、析出した沈殿をろ過で集めた。この沈殿を真空乾燥機で乾燥させ、下記式で表されるキノンジアジド化合物(a)を得た。
表2に示すポリマー3.5gをγ−ブチロラクトン6.5gに溶解させ、これに合成例5で得られたキノンジアジド化合物(a)を0.7g、KBM−1003(信越化学社製)を0.1g、ポリフロ−77(協和化学社製)0.5%乳酸エチル溶液を0.2g添加し、感光性ワニスとした。このワニスを6インチウェハーに回転塗布し、120℃のホットプレート(東京エレクトロン製、MARK−7)にて3分間処理し、厚さ7μmの被膜を得た。この被膜をi線ステッパー(GCA社製、DSW−8000)にて、0mJ/cm2から100mJ/cm2刻みで1000mJ/cm2まで露光し、露光後にテトラメチルアンモニウムハイドロオキサイド(TMAH)2.38%水溶液にて100秒間現像し、ついで純水でリンスして所望のパターンを得た。このとき、10μmの正方形パターンが開口している最も小さい露光量を感度として表2に示した。1000mJ/cm2以下を合格、それ以上を不合格とした。
表2に示すポリマー3.5gをγ−ブチロラクトン6.5gに溶解させ、これに光重合性化合物であるDCP−A(協和発酵社製)を0.5g、同じく光重合性化合物であるPDBE−250(日本油脂社製)を1.0g、同じく光重合性化合物であるMOI−BP(昭和電工社製)を0.5g、MX−270(日本カーバイド製)を0.5g、光重合開始剤であるOXE−02(チバスペシャリティーケミカルズ社製)を0.5g、KBM−573(信越化学社製)を0.1g、ポリフロ−77(協和化学社製)0.5%γ−ブチロラクトン溶液を0.2g添加し、感光性ワニスとした。このワニスを6インチウェハーに回転塗布し、120℃のホットプレート(東京エレクトロン製、MARK−7)にて3分間処理し、厚さ7μmの被膜を得た。この被膜をi線ステッパー(GCA社製、DSW−8000)にて、0mJ/cm2から100mJ/cm2刻みで1000mJ/cm2まで露光し、露光後に100℃のホットプレート(東京エレクトロン製、MARK−7)にて1分間処理した。続いて、テトラメチルアンモニウムハイドロオキサイド(TMAH)2.38%水溶液にて60秒間現像し、ついで純水でリンスして、所望のパターンを得た。このとき、30μmの正方形パターンが開口しており、かつ、パターン形状が逆テーパーになっていない最も小さい露光量を感度として表2に示した。感度は、1000mJ/cm2以下を合格、それ以上を不合格とした。
ポリマーとしてポリマーF1.4g、および、ノボラック樹脂化合物PSF−2808(群栄化学社製)2.1gを用いた以外は、実施例11〜20と同様にして感光性ワニスを作成し、評価した。結果を表2に示す。
Claims (8)
- 下記一般式(4)で表されるジイミダゾリド化合物と、下記一般式(2)で表されるジアミン化合物とを反応させるポリアミドの製造方法;
- 請求項1または2に記載の製造方法により得られるポリアミドおよび溶剤を含有する樹脂組成物。
- 光酸発生剤をさらに含有する請求項3記載の樹脂組成物。
- 光重合性化合物をさらに含有する請求項3記載の樹脂組成物。
- 一般式(2)中、R4がSO2、C(CF3)2またはフルオレン構造の残基である請求項4または5記載の樹脂組成物。
- さらにフェノール樹脂を含む請求項4〜6のいずれかに記載の樹脂組成物。
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