JP6259394B2 - ポリ(メタ)アクリレートの製造方法、これにより得られたポリ(メタ)アクリレート、モノマー組成物、その硬化物、およびこれを含むプリント配線板 - Google Patents
ポリ(メタ)アクリレートの製造方法、これにより得られたポリ(メタ)アクリレート、モノマー組成物、その硬化物、およびこれを含むプリント配線板 Download PDFInfo
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- JP6259394B2 JP6259394B2 JP2014507875A JP2014507875A JP6259394B2 JP 6259394 B2 JP6259394 B2 JP 6259394B2 JP 2014507875 A JP2014507875 A JP 2014507875A JP 2014507875 A JP2014507875 A JP 2014507875A JP 6259394 B2 JP6259394 B2 JP 6259394B2
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- meth
- acrylate
- isocyanate
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- poly
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- 239000000178 monomer Substances 0.000 title claims description 63
- 239000000203 mixture Substances 0.000 title claims description 55
- 229920000193 polymethacrylate Polymers 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 61
- 150000002513 isocyanates Chemical class 0.000 claims description 53
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 24
- 239000003999 initiator Substances 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 54
- -1 amine compound Chemical class 0.000 description 38
- 239000000126 substance Substances 0.000 description 24
- 239000011248 coating agent Substances 0.000 description 19
- 238000000576 coating method Methods 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 17
- 238000009413 insulation Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 12
- 239000000049 pigment Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001723 curing Methods 0.000 description 9
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000001879 gelation Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 6
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 239000002981 blocking agent Substances 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000005829 trimerization reaction Methods 0.000 description 5
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- 208000023514 Barrett esophagus Diseases 0.000 description 3
- 229920000298 Cellophane Polymers 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- UMLWXYJZDNNBTD-UHFFFAOYSA-N alpha-dimethylaminoacetophenone Natural products CN(C)CC(=O)C1=CC=CC=C1 UMLWXYJZDNNBTD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
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- 230000001678 irradiating effect Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 2
- 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 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
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- 229920001296 polysiloxane Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
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- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- OCQDPIXQTSYZJL-UHFFFAOYSA-N 1,4-bis(butylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCCC)=CC=C2NCCCC OCQDPIXQTSYZJL-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- CNRPDCKHCGUKDK-UHFFFAOYSA-N 1,8-bis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=C(SC=4C=CC=CC=4)C=CC=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 CNRPDCKHCGUKDK-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- HIQAWCBKWSQMRQ-UHFFFAOYSA-N 16-methylheptadecanoic acid;2-methylprop-2-enoic acid;propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(C)CCCCCCCCCCCCCCC(O)=O HIQAWCBKWSQMRQ-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 description 1
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
Images
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
-
- 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
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
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- Microelectronics & Electronic Packaging (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Description
ル基を有するモノマーを重合させることを特徴とする。
本発明のモノマー組成物は、熱硬化、光硬化、またはその双方により、密着性、耐薬品性、および耐熱性等の物理的特性に優れた硬化物(ポリ(メタ)アクリレート)とされるため、例えば、プリント配線板印刷用のインキまたはプリント配線板の被覆として適用可能である。
本発明では、(メタ)アクリロイル基を有するモノマーは、1分子中に1個以上の(メタ)アクリロイル基を有する。また、(メタ)アクリロイル基含有モノマーはイソシアネートと反応しうる官能基を持たない化合物であることが好ましい。
本発明では、イソシアネート基を含有する化合物として、脂肪族/脂環式イソシアネート、芳香族イソシアネート、およびブロックイソシアネートを使用することができる。
ブロック化剤としては、例えば、エタノール、n−プロパノール、イソプロパノール、t−ブタノール、イソブタノールなどのアルコール類、フェノール、クロルフェノール、クレゾール、キシレノール、p−ニトロフェノールなどのフェノール類、p−t−ブチルフェノール、p−sec−ブチルフェノール、p−sec−アミノフェノール、p−オクチルフェノール、p−ノニルフェノールなどのアルキルフェノール類、3−ヒドロキシピリジン、8−ヒドロキシキノリン、8−ヒドロキシキナルジンなどの塩基性窒素含有化合物、マロン酸ジエチル、アセト酢酸エチル、アセチルアセトンなどの活性メチレン化合物、アセトアミド、アクリルアミド、アセトアニリドなどの酸アミド類、コハク酸イミド、マレイン酸イミドなどの酸イミド類、2−エチルイミダゾール、2−エチル−4−メチルイミダゾールなどのイミダゾール類、ピラゾール、3−メチルピラゾール、3,5−ジメチルピラゾール等のピラゾール類、2−ピロリドン、ε−カプロラクタムなどのラクタム類、アセトキシム、メチルエチルケトンオキシム、シクロヘキサノンオキシム、アセトアルドキシムなどのケトンまたはアルデヒドのオキシム類、エチレンイミン、重亜硫酸塩などがあげられる。
また、本発明で使用されるモノマー組成物は、更に光重合開始剤を含んでもよい。光重合開始剤としては、エネルギー線の照射により、(メタ)アクリレートを重合させることが可能なものであれば、特に制限はなく、ラジカル重合開始剤が使用できる。
本発明のモノマー組成物には、必要に応じて消泡・レベリング剤、チクソトロピー付与剤・増粘剤、カップリング剤、分散剤、難燃剤等の添加剤を含有させることができる。
[実施例1〜11、および比較例1〜4]
表1に示す割合で各成分を配合し、これをディゾルバーで攪拌して本発明のモノマー組成物および比較モノマー組成物を得た。
本発明のモノマー組成物に対し、ゲル化試験機(日新科学社製ゲル化試験機)を用いて以下のように所定の温度で加熱し、ゲル化するまでの時間を測定した。結果を表1に記載する。
実施例1〜8: 150℃
実施例9〜11: 170℃
比較例1: 150℃
比較例2〜4: 170℃
固形分70% NCO分 9.2%
1,6−ヘキサメチレンジイソシアネートのトリマーをジメチルピラゾールと(活性メチレン化合物)ジエチルマロネートでブロックしたもの
固形分60% NCO分 6.6%
1,6−ヘキサメチレンジイソシアネートを活性メチレン化合物でブロックしたもの
固形分75% NCO分 10.5%
1,6−ヘキサメチレンジイソシアネートのトリマーをジメチルピラゾールでブロックしたもの
実施例1および比較例1の組成物について、セイコーインスツル社製EXSTARを用い、示差走査熱量測定(DSC)を行った。得られたDSC曲線を図1に示す。
実施例1の組成物について、パーキンエルマージャパン社製Spectrum100を用い、赤外分光法(IR Spectroscopy)による吸光度(absorption)を測定した。なお、マクロATRユニットとして、smiths Dura Sampl IRIIを用いた。
[実施例12、13、および比較例5]
1.紫外線照射工程
表2に示す割合で各成分を配合し、これをディゾルバーで攪拌して本発明のモノマー組成物および比較モノマー組成物を得た。
アクリレート1:トリメチロールプロパントリアクリレート(TMPTA)
東亞合成社製 M-309
光重合開始剤1:BASFジャパン社製 イルガキュア907
光重合開始剤2:BASFジャパン社製 イルガキュア127
イソシアネート1:m−キシリレンジイソシアネート
ブロックイソシアネート2:ブロックイソシアネート2:Baxenden社製 BI7992
固形分70% NCO分 9.2%(1,6−ヘキサメチレンジイソシアネートを活性メチレン化合物でブロックしたもの)
レベリング剤:ビックケミー・ジャパン社製 BYK−307
A.紫外線照射サンプル:FR−4/10μ
本発明のモノマー組成物および比較モノマー組成物を150mm×95mm×1.6mmのFR-4銅張り積層板(基板)に、バーコーターにより厚さ10μmになるように塗布した未硬化サンプルを、各試験用に多数作成した。これらの未硬化サンプルに、高圧水銀灯にて、積算光量150mJ/cm2の紫外線を照射した。
紫外線照射工程後の各サンプル(紫外線照射サンプル:FR−4/10μ)を、下記の密着性試験、鉛筆硬度硬度試験、耐薬品性試験、耐熱試験に付した。試験結果を表3に記載する。
B.紫外線照射・加熱サンプル:FR−4/10μ
紫外線照射サンプル:FR−4/10μを、熱風循環式乾燥炉により150℃で30分間加熱して、紫外線照射・加熱後のサンプル(紫外線照射・加熱サンプル:FR-4/10μ)を得た。このサンプルを下記の密着性試験、鉛筆硬度硬度試験、耐薬品性試験、および耐熱試験に付した。試験結果を表4に記載する。
C.紫外線照射・加熱サンプル::Bクーポン/40μ
本発明のモノマー組成物および比較モノマー組成物を、IPC B−25テストパターンのクシ型電極Bクーポン(基板)に厚さ40μmになるように塗布して、上記と同様の紫外線照射、次いで上記と同様の加熱を行うことにより、紫外線照射・加熱のサンプル:Bクーポン/40μを得た。これを下記の絶縁性試験に付した。
上記各サンプルについて以下に示す特性試験を行った。
各サンプルの塗膜表面にカッターナイフで1mm間隔、縦横11本の切れ目を入れて、塗膜表面の縦横の切れ目に囲まれた100のカット区画上にセロハンテープを貼付し、剥離して、テープにより引きはがされずにFR-4に残存している塗膜のカット区画の数を調べた。
各サンプルを作製し、JISK5400に従い、三菱鉛筆製Hi-uniを用いて鉛筆硬度試験を測定した。
具体的には、鉛筆の木部を削りとり、芯は5〜6mmの長さにした。芯先端を研磨紙で平滑に研磨しで円形の断面を得た鉛筆を使用した。この鉛筆を、サンプル表面に対して45度の角度で保持し、サンプル表面に施される加重1kgとして、45度の角度で塗膜を引っかいた。塗膜が基板まで達しなかった鉛筆の最大の硬度を表2に記載した。
各サンプルを、10%の硫酸水溶液に室温で30分浸漬させ、これを取り出した後に水洗・乾燥させた。乾燥後の各サンプルについて、塗膜の状態を目視評価後、セロテープ(登録商標)でピーリングを行い、以下のとおり評価した。
○:塗膜の状態に全く変化がない。
×:塗膜に浮き、はがれがある。または、セロテープ(登録商標)に大きく転写するはがれがある。
各サンプルにロジン系フラックス(サンワ化学社製SF−270)を塗布して、260℃のはんだ槽に10秒間浸漬した。各サンプルをはんだ層から取り出して自然冷却した後、プロピレングリコールモノメチルエーテルアセテートで洗浄し、乾燥した。この試験を3回繰返した後、各試験片の塗膜の状態を目視評価後、セロテープ(登録商標)でピーリングを行い、以下のとおり評価した。
○:塗膜の状態に全く変化がない。
△:目視では変化が無いが、セロテープ(登録商標)ピーリングでは若干のはがれがある。
×:塗膜に浮き、はがれがある。または、セロテープ(登録商標)に大きく転写するはがれがある。
先に述べた紫外線照射サンプル:Bクーポン/40μに、DC500Vのバイアスを印加し、絶縁抵抗値を測定した。以下のとおり評価した。
○:絶縁抵抗値≧100GΩ
×:絶縁抵抗値<100GΩ
(密着性試験、鉛筆硬度試験、耐薬品性試験、および耐熱性試験)
(密着性試験、鉛筆硬度硬度試験、耐薬品性試験、および耐熱試験)
C.紫外線照射・加熱サンプル:Bクーポン/40μについての試験結果(絶縁性試験)
Claims (3)
- イソシアネートと反応しうる官能基を持たない(メタ)アクリロイル基を有するモノマーに、多官能イソシアネートを添加して得られたモノマー組成物(但し、カルボキシル基を含有するバインダーポリマーを含まない)を、140℃から170℃で加熱することにより、前記(メタ)アクリロイル基を有するモノマーを重合させることを特徴とするポリ(メタ)アクリレートの製造方法。
- 前記モノマー組成物に、さらに光重合開始剤を添加して、活性エネルギー線を照射することにより前記(メタ)アクリロイル基を有するモノマーを光硬化させた後、前記加熱により前記(メタ)アクリロイル基を有するモノマーを重合させることを特徴とする請求項1記載の製造方法。
- 請求項1または2記載の製造方法に用いられることを特徴とするモノマー組成物。
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US4117235A (en) * | 1971-09-23 | 1978-09-26 | Owens-Illinois, Inc. | Novel preparation of novel low molecular weight, liquid polymer |
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US8178204B2 (en) * | 2008-03-05 | 2012-05-15 | Bayer Materialscience Llc | Acrylate-modified aspartates and gel coat compositions made therefrom |
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DE102009055061A1 (de) * | 2009-12-21 | 2011-06-22 | Evonik Degussa GmbH, 45128 | Neues Initiierungsverfahren zur Polymerisation von (Meth)acrylaten |
CN103339153B (zh) * | 2011-01-27 | 2015-04-29 | 株式会社自动网络技术研究所 | 链转移剂、感光性组合物、感光性组合物的固化物及感光性组合物的固化方法 |
JP5802396B2 (ja) * | 2011-01-27 | 2015-10-28 | 株式会社オートネットワーク技術研究所 | 紫外線硬化性組成物およびこれを用いた硬化物 |
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