CA1048196A - Photopolymerizable systems containing cyclic amides as gelation inhibitor - Google Patents
Photopolymerizable systems containing cyclic amides as gelation inhibitorInfo
- Publication number
- CA1048196A CA1048196A CA219,036A CA219036A CA1048196A CA 1048196 A CA1048196 A CA 1048196A CA 219036 A CA219036 A CA 219036A CA 1048196 A CA1048196 A CA 1048196A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- mixture
- polymerizable material
- catalyst precursor
- polymerizable
- 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
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 25
- 150000003950 cyclic amides Chemical class 0.000 title claims abstract description 24
- 238000001879 gelation Methods 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 81
- 150000002118 epoxides Chemical class 0.000 claims abstract description 28
- 239000012018 catalyst precursor Substances 0.000 claims abstract description 21
- 150000002596 lactones Chemical class 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011951 cationic catalyst Substances 0.000 claims abstract description 6
- 230000005855 radiation Effects 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims description 35
- -1 aromatic diazonium salt Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 15
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 239000012954 diazonium Substances 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000000087 stabilizing effect Effects 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000003106 haloaryl group Chemical group 0.000 claims 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical group O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims 1
- 229960000380 propiolactone Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000009472 formulation Methods 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 13
- 238000000576 coating method Methods 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 150000001261 hydroxy acids Chemical class 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000011968 lewis acid catalyst Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- GDUHOQKSPBXQAW-UHFFFAOYSA-N 2,5-dimethoxy-4-(4-methylphenyl)benzenediazonium Chemical compound C1=C([N+]#N)C(OC)=CC(C=2C=CC(C)=CC=2)=C1OC GDUHOQKSPBXQAW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DBEQHSWUYRYJMT-UHFFFAOYSA-N 4-chlorobenzenediazonium Chemical compound ClC1=CC=C([N+]#N)C=C1 DBEQHSWUYRYJMT-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 241001163743 Perlodes Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical compound N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000001145 hydrido group Chemical group *[H] 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003999 initiator Substances 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
- 238000002156 mixing Methods 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
- 239000011087 paperboard Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010944 pre-mature reactiony Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- NGZXDRGWBULKFA-NSOVKSMOSA-N (+)-Bebeerine Chemical compound C([C@@H]1N(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CCN3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 NGZXDRGWBULKFA-NSOVKSMOSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical class O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- LTSWUFKUZPPYEG-UHFFFAOYSA-N 1-decoxydecane Chemical compound CCCCCCCCCCOCCCCCCCCCC LTSWUFKUZPPYEG-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- XZXOKXALOUWXKS-UHFFFAOYSA-N 2,4-dimethyl-6-nitrobenzenediazonium Chemical compound CC1=CC(C)=C([N+]#N)C([N+]([O-])=O)=C1 XZXOKXALOUWXKS-UHFFFAOYSA-N 0.000 description 1
- STMCLPOXTRJQKV-UHFFFAOYSA-N 2,5-diethoxy-4-(4-ethoxyphenyl)benzenediazonium Chemical compound C1=CC(OCC)=CC=C1C1=CC(OCC)=C([N+]#N)C=C1OCC STMCLPOXTRJQKV-UHFFFAOYSA-N 0.000 description 1
- MADGGJXZXKOPDW-UHFFFAOYSA-N 2,5-dimethoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OC)=CC(N2CCOCC2)=C1OC MADGGJXZXKOPDW-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- NPKKFQUHBHQTSH-UHFFFAOYSA-N 2-(decoxymethyl)oxirane Chemical compound CCCCCCCCCCOCC1CO1 NPKKFQUHBHQTSH-UHFFFAOYSA-N 0.000 description 1
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- HRWYHCYGVIJOEC-UHFFFAOYSA-N 2-(octoxymethyl)oxirane Chemical compound CCCCCCCCOCC1CO1 HRWYHCYGVIJOEC-UHFFFAOYSA-N 0.000 description 1
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- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
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- RNBOFGSATMLBRI-UHFFFAOYSA-N 2-methyl-4-nitrobenzenediazonium Chemical compound CC1=CC([N+]([O-])=O)=CC=C1[N+]#N RNBOFGSATMLBRI-UHFFFAOYSA-N 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- UVSNPDMUGCTOGJ-UHFFFAOYSA-N methoxymethoxyethene Chemical compound COCOC=C UVSNPDMUGCTOGJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-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
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 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
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S528/931—Physical treatment of natural rubber or natural rubber containing material or chemical treatment of non-rubber portion thereof, e.g. extraction of rubber from milk weed
- Y10S528/934—Latex
- Y10S528/935—Preserving or stabilizing
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Epoxy Resins (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Paints Or Removers (AREA)
- Polyethers (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/447,209 US3951769A (en) | 1974-03-01 | 1974-03-01 | Epoxide photopolymerizable compositions containing cyclic amides as gelation inhibitor and methods of polymerizing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1048196A true CA1048196A (en) | 1979-02-06 |
Family
ID=23775430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA219,036A Expired CA1048196A (en) | 1974-03-01 | 1975-01-30 | Photopolymerizable systems containing cyclic amides as gelation inhibitor |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3951769A (en:Method) |
| JP (1) | JPS5817215B2 (en:Method) |
| CA (1) | CA1048196A (en:Method) |
| CH (1) | CH606185A5 (en:Method) |
| DE (1) | DE2439547A1 (en:Method) |
| FR (1) | FR2262679B1 (en:Method) |
| GB (1) | GB1452675A (en:Method) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5337120B2 (en:Method) * | 1974-12-20 | 1978-10-06 | ||
| JPS59174620A (ja) * | 1983-03-23 | 1984-10-03 | Nippon Oil & Fats Co Ltd | 顔料分散用熱硬化性樹脂 |
| JPH064694B2 (ja) * | 1983-04-28 | 1994-01-19 | 三井東圧化学株式会社 | 紫外線硬化組成物 |
| US4574132A (en) * | 1984-11-09 | 1986-03-04 | The United States Of America As Represented By The Secretary Of The Army | General purpose expandable adhesive |
| JPS61133514A (ja) * | 1984-11-30 | 1986-06-20 | 三菱電機株式会社 | 絶縁導体の製造方法 |
| JPH036213A (ja) * | 1989-06-01 | 1991-01-11 | Matsushita Electric Ind Co Ltd | 紫外線硬化型樹脂 |
| US6187965B1 (en) | 1998-11-06 | 2001-02-13 | International Business Machines Corporation | Process for recovering high boiling solvents from a photolithographic waste stream comprising at least 10 percent by weight of monomeric units |
| US5994597A (en) * | 1998-11-06 | 1999-11-30 | International Business Machines Corporation | Process for recovering high boiling solvents from a photolithographic waste stream comprising less than 10 percent by weight monomeric units |
| US20040266913A1 (en) * | 2001-09-13 | 2004-12-30 | Hiroaki Yamaguchi | Cationic polymerizable adhesive composition and anisotropically electroconductive adhesive composition |
| JP2004323642A (ja) * | 2003-04-23 | 2004-11-18 | Riso Kagaku Corp | カチオン重合性組成物及びインク |
| CA2607416A1 (en) * | 2005-04-22 | 2006-10-26 | Sun Chemical B.V. | An ink jet ink |
| WO2025018368A1 (ja) * | 2023-07-18 | 2025-01-23 | 株式会社レゾナック | 接着剤組成物、回路接続用接着剤フィルム、接続構造体及び接続構造体の製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2826501A (en) * | 1956-12-20 | 1958-03-11 | Litho Chemical And Supply Co I | Lithographic coating solution and lithographic plates coated therewith |
| US3708296A (en) * | 1968-08-20 | 1973-01-02 | American Can Co | Photopolymerization of epoxy monomers |
| US3679419A (en) * | 1969-05-20 | 1972-07-25 | Azoplate Corp | Light-sensitive diazo condensate containing reproduction material |
| US3660097A (en) * | 1969-11-28 | 1972-05-02 | Polychrome Corp | Diazo-polyurethane light-sensitive compositions |
| US3709861A (en) * | 1970-12-14 | 1973-01-09 | Shell Oil Co | Process for light-induced curing of epoxy resins in presence of cyclopentadienylmanganese tricarbonyl compounds |
| US3790382A (en) * | 1971-04-16 | 1974-02-05 | Minnesota Mining & Mfg | Fluorinated polyamide-diazo resin coating composition |
| US3817850A (en) * | 1971-05-18 | 1974-06-18 | American Can Co | Photopolymerizable epoxy systems containing substituted acyclic amides or substituted ureas as gelation inhibitors |
| US3817845A (en) * | 1971-05-18 | 1974-06-18 | American Can Co | Photopolymerizable epoxy systems containing sulfoxide gelation inhibitors |
| US3721617A (en) * | 1971-05-18 | 1973-03-20 | American Can Co | Photopolymerizable epoxy systems containing cyclic amide gelation inhibitors |
| US3711390A (en) * | 1971-05-18 | 1973-01-16 | J Feinberg | Photopolymerizable epoxy systems containing substituted cyclic amides or substituted ureas as gelation inhibitors |
-
1974
- 1974-03-01 US US05/447,209 patent/US3951769A/en not_active Expired - Lifetime
- 1974-08-17 DE DE2439547A patent/DE2439547A1/de not_active Withdrawn
- 1974-08-20 CH CH1137774A patent/CH606185A5/xx not_active IP Right Cessation
- 1974-08-23 FR FR7429072A patent/FR2262679B1/fr not_active Expired
- 1974-09-06 JP JP49102874A patent/JPS5817215B2/ja not_active Expired
- 1974-10-14 GB GB4452174A patent/GB1452675A/en not_active Expired
-
1975
- 1975-01-30 CA CA219,036A patent/CA1048196A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3951769A (en) | 1976-04-20 |
| JPS5817215B2 (ja) | 1983-04-05 |
| FR2262679A1 (en:Method) | 1975-09-26 |
| GB1452675A (en) | 1976-10-13 |
| JPS50119898A (en:Method) | 1975-09-19 |
| DE2439547A1 (de) | 1975-09-04 |
| FR2262679B1 (en:Method) | 1978-04-28 |
| CH606185A5 (en:Method) | 1978-10-31 |
| AU7169474A (en) | 1976-01-29 |
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