DE69932320T2 - Maleimide enthaltende fotopolymerisierbare zusammensetzungen und verfahren zu deren verwendung - Google Patents
Maleimide enthaltende fotopolymerisierbare zusammensetzungen und verfahren zu deren verwendung Download PDFInfo
- Publication number
- DE69932320T2 DE69932320T2 DE69932320T DE69932320T DE69932320T2 DE 69932320 T2 DE69932320 T2 DE 69932320T2 DE 69932320 T DE69932320 T DE 69932320T DE 69932320 T DE69932320 T DE 69932320T DE 69932320 T2 DE69932320 T2 DE 69932320T2
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- Germany
- Prior art keywords
- maleimide
- group
- alkyl
- aryl
- compound
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 title claims abstract description 17
- -1 benzophenone compound Chemical class 0.000 claims abstract description 47
- 239000012965 benzophenone Substances 0.000 claims abstract description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 5
- 230000001678 irradiating effect Effects 0.000 claims abstract description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 35
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 239000003999 initiator Substances 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 17
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 13
- PYCNXFLQHZMWJL-UHFFFAOYSA-N 3-(2-hydroxyethyl)pyrrole-2,5-dione Chemical compound OCCC1=CC(=O)NC1=O PYCNXFLQHZMWJL-UHFFFAOYSA-N 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 230000009021 linear effect Effects 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 claims description 10
- 230000000977 initiatory effect Effects 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 239000010703 silicon Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 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 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
- 125000006850 spacer group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- CGCQHMFVCNWSOV-UHFFFAOYSA-N (4-morpholin-4-ylphenyl)-phenylmethanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C1=CC=CC=C1 CGCQHMFVCNWSOV-UHFFFAOYSA-N 0.000 claims description 5
- DDOXBGKIXOWCSH-UHFFFAOYSA-N 2-(2,5-dioxopyrrol-3-yl)ethyl acetate Chemical compound CC(=O)OCCC1=CC(=O)NC1=O DDOXBGKIXOWCSH-UHFFFAOYSA-N 0.000 claims description 5
- ZTFBCEOQDXQPEE-UHFFFAOYSA-N 3,4-diethylpyrrole-2,5-dione;ethyl carbamate;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound CCOC(N)=O.CCOC(N)=O.CC1=CC(=O)CC(C)(C)C1.CCC1=C(CC)C(=O)NC1=O ZTFBCEOQDXQPEE-UHFFFAOYSA-N 0.000 claims description 5
- APKSTKKPFBLQBB-UHFFFAOYSA-N 3-(hydroxymethyl)pyrrole-2,5-dione Chemical compound OCC1=CC(=O)NC1=O APKSTKKPFBLQBB-UHFFFAOYSA-N 0.000 claims description 5
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 claims description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 5
- VCTPVICUDLXAIQ-UHFFFAOYSA-N ethyl hydrogen carbonate;3-ethylpyrrole-2,5-dione Chemical compound CCOC(O)=O.CCC1=CC(=O)NC1=O VCTPVICUDLXAIQ-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- BSILAEQTGTZMIW-UHFFFAOYSA-N bis(4-phenoxyphenyl)methanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 BSILAEQTGTZMIW-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- QULUBUSLQYTMMQ-UHFFFAOYSA-N 3-(3-oxopent-4-enyl)pyrrole-2,5-dione Chemical compound C=CC(=O)CCC1=CC(=O)NC1=O QULUBUSLQYTMMQ-UHFFFAOYSA-N 0.000 claims description 3
- UJTRCPVECIHPBG-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C2CCCCC2)=C1 UJTRCPVECIHPBG-UHFFFAOYSA-N 0.000 claims description 3
- MXVZVCCKUVRGQC-UHFFFAOYSA-N 3-hexylpyrrole-2,5-dione Chemical compound CCCCCCC1=CC(=O)NC1=O MXVZVCCKUVRGQC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 3
- LTYBJDPMCPTGEE-UHFFFAOYSA-N (4-benzoylphenyl) prop-2-enoate Chemical compound C1=CC(OC(=O)C=C)=CC=C1C(=O)C1=CC=CC=C1 LTYBJDPMCPTGEE-UHFFFAOYSA-N 0.000 claims description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 2
- HDKOABXUWJNFJJ-UHFFFAOYSA-N 2-(2-ethylhexoxy)-1-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(C)C(OCC(CC)CCCC)=CC=C3SC2=C1 HDKOABXUWJNFJJ-UHFFFAOYSA-N 0.000 claims description 2
- CTVKFDPYSMGNCE-UHFFFAOYSA-N 2-[2-(2-carboxyoxyethoxy)ethoxy]ethyl hydrogen carbonate Chemical compound OC(=O)OCCOCCOCCOC(O)=O CTVKFDPYSMGNCE-UHFFFAOYSA-N 0.000 claims description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 2
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical class OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 2
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 229920003180 amino resin Polymers 0.000 claims description 2
- QRQHCGWCUVLPSQ-UHFFFAOYSA-N bis(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QRQHCGWCUVLPSQ-UHFFFAOYSA-N 0.000 claims description 2
- LTZMYKBGNHJFLB-UHFFFAOYSA-N bis[4-(4-propan-2-ylphenoxy)phenyl]methanone Chemical compound C1=CC(C(C)C)=CC=C1OC1=CC=C(C(=O)C=2C=CC(OC=3C=CC(=CC=3)C(C)C)=CC=2)C=C1 LTZMYKBGNHJFLB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 claims description 2
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 2
- ZTHZEDRPKCLGAR-UHFFFAOYSA-N 1-(2-bromophenyl)pyrrole-2,5-dione Chemical compound BrC1=CC=CC=C1N1C(=O)C=CC1=O ZTHZEDRPKCLGAR-UHFFFAOYSA-N 0.000 claims 1
- KPQOXMCRYWDRSB-UHFFFAOYSA-N 1-(2-chlorophenyl)pyrrole-2,5-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C=CC1=O KPQOXMCRYWDRSB-UHFFFAOYSA-N 0.000 claims 1
- XKQAFSGPGGEGPU-UHFFFAOYSA-N 1-(2-fluorophenyl)pyrrole-2,5-dione Chemical compound FC1=CC=CC=C1N1C(=O)C=CC1=O XKQAFSGPGGEGPU-UHFFFAOYSA-N 0.000 claims 1
- NHWYMYDMYCNUKI-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3,5-diethylphenyl]methyl]-2,6-diethylphenyl]pyrrole-2,5-dione Chemical compound C=1C(CC)=C(N2C(C=CC2=O)=O)C(CC)=CC=1CC(C=C1CC)=CC(CC)=C1N1C(=O)C=CC1=O NHWYMYDMYCNUKI-UHFFFAOYSA-N 0.000 claims 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims 1
- HVCQSNXTTXPIAD-UHFFFAOYSA-N 1-chloroxanthen-9-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl HVCQSNXTTXPIAD-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 18
- 230000005855 radiation Effects 0.000 abstract description 14
- 150000003923 2,5-pyrrolediones Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 238000009472 formulation Methods 0.000 description 26
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- 239000013078 crystal Substances 0.000 description 18
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 18
- 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 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
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- 238000002474 experimental method Methods 0.000 description 13
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- 239000000047 product Substances 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 238000010992 reflux Methods 0.000 description 8
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
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- 150000001412 amines Chemical class 0.000 description 6
- 150000008366 benzophenones Chemical class 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 231100000489 sensitizer Toxicity 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
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- 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 5
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 5
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
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Classifications
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- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/12—Esters of phenols or saturated alcohols
- C08F22/18—Esters containing halogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- 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
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pyrrole Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7310098P | 1998-01-30 | 1998-01-30 | |
| US73100P | 1998-01-30 | ||
| PCT/US1999/001989 WO1999039247A1 (en) | 1998-01-30 | 1999-01-29 | Photopolymerization compositions including maleimides and processes for using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69932320D1 DE69932320D1 (de) | 2006-08-24 |
| DE69932320T2 true DE69932320T2 (de) | 2007-07-12 |
Family
ID=22111727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69932320T Expired - Fee Related DE69932320T2 (de) | 1998-01-30 | 1999-01-29 | Maleimide enthaltende fotopolymerisierbare zusammensetzungen und verfahren zu deren verwendung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6555593B1 (https=) |
| EP (1) | EP1051665B1 (https=) |
| JP (1) | JP2002502056A (https=) |
| KR (1) | KR100594956B1 (https=) |
| CN (1) | CN1295680A (https=) |
| AT (1) | ATE333114T1 (https=) |
| AU (1) | AU2485199A (https=) |
| BR (1) | BR9908044A (https=) |
| CA (1) | CA2318809A1 (https=) |
| DE (1) | DE69932320T2 (https=) |
| TW (1) | TWI238841B (https=) |
| WO (1) | WO1999039247A1 (https=) |
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| SE516275C2 (sv) * | 2000-03-13 | 2001-12-10 | Perstorp Flooring Ab | Ny oligomerförening samt användning därav |
| DE60136592D1 (de) * | 2000-06-19 | 2009-01-02 | Toagosei Co Ltd | Vernetzbare Harzzusammensetzungen |
| WO2002020500A2 (en) * | 2000-09-01 | 2002-03-14 | Icos Corporation | Materials and methods to potentiate cancer treatment |
| EP1391476B1 (en) * | 2001-04-09 | 2015-12-09 | Sekisui Chemical Co., Ltd. | Photoreactive composition |
| US20080103222A1 (en) * | 2002-04-26 | 2008-05-01 | Albemarle Corporation | New Class of Amine Coinitiators in Photoinitiated Polymerizations |
| US20040029044A1 (en) * | 2002-08-08 | 2004-02-12 | 3M Innovative Properties Company | Photocurable composition |
| CA2523178C (en) | 2003-03-24 | 2012-10-23 | Luitpold Pharmaceuticals, Inc. | Materials and methods to potentiate cancer treatment |
| US20040198859A1 (en) * | 2003-04-03 | 2004-10-07 | Nguyen Chau K. | Photopolymerization systems and their use |
| US20060293404A1 (en) * | 2003-04-24 | 2006-12-28 | Santobianco John G | New class of amine coinitiators in photoinitiated polymerizations |
| US20060009539A1 (en) * | 2004-07-12 | 2006-01-12 | Herr Donald E | Maleimide-based radiation curable compositions |
| JP4994036B2 (ja) * | 2004-07-15 | 2012-08-08 | 太陽ホールディングス株式会社 | 光硬化性及び熱硬化性樹脂組成物及びその硬化物 |
| KR100618864B1 (ko) * | 2004-09-23 | 2006-08-31 | 삼성전자주식회사 | 반도체 소자 제조용 마스크 패턴 및 그 형성 방법과 미세패턴을 가지는 반도체 소자의 제조 방법 |
| CN100360504C (zh) * | 2005-12-22 | 2008-01-09 | 上海交通大学 | 含硫可聚合的二苯甲酮光引发剂及其制备方法 |
| WO2007092935A1 (en) * | 2006-02-08 | 2007-08-16 | Albemarle Corporation | Hydroxyalkylaminoalkylthioxanthones |
| DK1988910T3 (en) | 2006-02-28 | 2018-01-22 | Kodiak Sciences Inc | ACRYLOYLOXYETHYLPHOSPHORYLCHOLINE-CONTAINING POLYMER CONJUGATES AND PREPARATION thereof |
| CN100372832C (zh) * | 2006-04-20 | 2008-03-05 | 上海交通大学 | 一种含硫和二苯甲酮结构的二胺及其制备方法 |
| US7709545B2 (en) | 2006-12-05 | 2010-05-04 | The University Of Southern Mississippi | Benzophenone/thioxanthone derivatives and their use in photopolymerizable compositions |
| JP2009214428A (ja) * | 2008-03-11 | 2009-09-24 | Fujifilm Corp | 平版印刷版原版および平版印刷方法 |
| KR101099691B1 (ko) * | 2008-04-07 | 2011-12-28 | 주식회사 삼양이엠에스 | 음성 레지스트 조성물 |
| DE102008054611A1 (de) * | 2008-12-15 | 2010-06-17 | Evonik Röhm Gmbh | Verfahren zur Herstellung von methacrylierten Benzophenonen |
| US8765432B2 (en) * | 2009-12-18 | 2014-07-01 | Oligasis, Llc | Targeted drug phosphorylcholine polymer conjugates |
| US20130025495A1 (en) * | 2010-01-11 | 2013-01-31 | Isp Investments Inc. | Compositions comprising a reactive monomer and uses thereof |
| JP5615600B2 (ja) * | 2010-06-09 | 2014-10-29 | 富士フイルム株式会社 | インクジェット記録用インク組成物、インクジェット記録方法及びインクジェット印画物 |
| JP5724298B2 (ja) * | 2010-10-29 | 2015-05-27 | 大日本印刷株式会社 | ガスバリア性フィルムの製造方法及びガスバリア層の形成方法 |
| JP6463361B2 (ja) | 2013-09-08 | 2019-01-30 | コディアック サイエンシーズ インコーポレイテッドＫｏｄｉａｋ Ｓｃｉｅｎｃｅｓ Ｉｎｃ． | 第ｖｉｉｉ因子両性イオンポリマーコンジュゲート |
| US9840553B2 (en) | 2014-06-28 | 2017-12-12 | Kodiak Sciences Inc. | Dual PDGF/VEGF antagonists |
| KR20210013299A (ko) | 2014-10-17 | 2021-02-03 | 코디악 사이언시스 인코포레이티드 | 부티릴콜린에스테라제 양성이온성 중합체 컨쥬게이트 |
| BR112017009711B1 (pt) * | 2014-11-13 | 2021-06-01 | Rhodia Operations | Composições, pasta de dentes, gel dental, dentifrício, pó dental, pasta profilática, enxaguante bucal, solução para enxágue, mousse dental, fio dental, goma de mascar, tira ou filme de cuidados bucais solúveis para aplicação direta ou fixação a uma superfície bucal, composto de fosfato e método de cuidados bucais |
| KR102799807B1 (ko) | 2015-12-30 | 2025-04-24 | 코디악 사이언시스 인코포레이티드 | 항체 및 이의 접합체 |
| MX2020009152A (es) | 2018-03-02 | 2020-11-09 | Kodiak Sciences Inc | Anticuerpos de il-6 y constructos de fusion y conjugados de los mismos. |
| WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CA3157509A1 (en) | 2019-10-10 | 2021-04-15 | Kodiak Sciences Inc. | Methods of treating an eye disorder |
| US11421049B2 (en) * | 2019-11-13 | 2022-08-23 | Piedmont Chemical Industries, LLC | Photopolymerization synergist |
| US11639398B2 (en) * | 2019-12-30 | 2023-05-02 | Rohm And Haas Electronic Materials Llc | Photosensitive bismaleimide composition |
| US11434313B2 (en) * | 2020-12-16 | 2022-09-06 | Canon Kabushiki Kaisha | Curable composition for making cured layer with high thermal stability |
| CN114163551A (zh) * | 2021-12-02 | 2022-03-11 | 广东博兴新材料科技有限公司 | 一种水性uv/eb敏感树脂及其制备方法和应用 |
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| WO1998007759A1 (en) * | 1996-08-23 | 1998-02-26 | First Chemical Corporation | Polymerization processes using aliphatic maleimides |
| WO1998054134A1 (en) * | 1997-05-27 | 1998-12-03 | First Chemical Coporation | Aromatic maleimides and their use as photoinitiators |
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-
1999
- 1999-01-29 AT AT99904452T patent/ATE333114T1/de not_active IP Right Cessation
- 1999-01-29 TW TW088101423A patent/TWI238841B/zh active
- 1999-01-29 AU AU24851/99A patent/AU2485199A/en not_active Abandoned
- 1999-01-29 JP JP2000529640A patent/JP2002502056A/ja active Pending
- 1999-01-29 US US09/240,020 patent/US6555593B1/en not_active Expired - Fee Related
- 1999-01-29 DE DE69932320T patent/DE69932320T2/de not_active Expired - Fee Related
- 1999-01-29 WO PCT/US1999/001989 patent/WO1999039247A1/en not_active Ceased
- 1999-01-29 BR BR9908044-3A patent/BR9908044A/pt not_active IP Right Cessation
- 1999-01-29 CA CA002318809A patent/CA2318809A1/en not_active Abandoned
- 1999-01-29 KR KR1020007008321A patent/KR100594956B1/ko not_active Expired - Fee Related
- 1999-01-29 CN CN99804722A patent/CN1295680A/zh active Pending
- 1999-01-29 EP EP99904452A patent/EP1051665B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010040466A (ko) | 2001-05-15 |
| AU2485199A (en) | 1999-08-16 |
| ATE333114T1 (de) | 2006-08-15 |
| EP1051665A1 (en) | 2000-11-15 |
| EP1051665B1 (en) | 2006-07-12 |
| BR9908044A (pt) | 2000-11-28 |
| TWI238841B (en) | 2005-09-01 |
| CN1295680A (zh) | 2001-05-16 |
| DE69932320D1 (de) | 2006-08-24 |
| CA2318809A1 (en) | 1999-08-05 |
| US6555593B1 (en) | 2003-04-29 |
| JP2002502056A (ja) | 2002-01-22 |
| WO1999039247A1 (en) | 1999-08-05 |
| KR100594956B1 (ko) | 2006-06-30 |
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