CN104203992B - Poly-(methyl) acrylate and manufacture method, monomer composition, solidfied material and printed circuit board (PCB) - Google Patents
Poly-(methyl) acrylate and manufacture method, monomer composition, solidfied material and printed circuit board (PCB) Download PDFInfo
- Publication number
- CN104203992B CN104203992B CN201380017235.5A CN201380017235A CN104203992B CN 104203992 B CN104203992 B CN 104203992B CN 201380017235 A CN201380017235 A CN 201380017235A CN 104203992 B CN104203992 B CN 104203992B
- Authority
- CN
- China
- Prior art keywords
- methyl
- acrylate
- monomer
- monomer composition
- acryloyl group
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 239000000178 monomer Substances 0.000 title claims abstract description 68
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000000463 material Substances 0.000 title claims description 33
- -1 (methyl) acryloyl group Chemical group 0.000 claims abstract description 96
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 238000010438 heat treatment Methods 0.000 claims description 21
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000000016 photochemical curing Methods 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 3
- 229920001228 polyisocyanate Polymers 0.000 claims 1
- 239000005056 polyisocyanate Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 29
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 230000006978 adaptation Effects 0.000 abstract description 9
- 239000012948 isocyanate Substances 0.000 description 54
- 150000002513 isocyanates Chemical class 0.000 description 48
- 238000012360 testing method Methods 0.000 description 48
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 33
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 27
- 150000002148 esters Chemical class 0.000 description 24
- 239000002253 acid Substances 0.000 description 21
- 239000000049 pigment Substances 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 10
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 10
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000001879 gelation Methods 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 238000004040 coloring Methods 0.000 description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- 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 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000005520 cutting process Methods 0.000 description 5
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- 238000005829 trimerization reaction Methods 0.000 description 5
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 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
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 150000003217 pyrazoles Chemical class 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 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
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000013007 heat curing Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-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
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 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
- 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 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
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 2
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- VTYWZDWSGZRBBW-UHFFFAOYSA-N C(CCCCCCC)[Zr]CCCCCCCC Chemical compound C(CCCCCCC)[Zr]CCCCCCCC VTYWZDWSGZRBBW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Natural products CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- VELFFNYFZHVFNA-UHFFFAOYSA-N dioctyl phosphono phosphate Chemical compound CCCCCCCCOP(=O)(OP(O)(O)=O)OCCCCCCCC VELFFNYFZHVFNA-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 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
- 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
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 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
- 230000000007 visual effect Effects 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 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BGFGHXUTCFJTLE-UHFFFAOYSA-N 1,1,3-triaminourea Chemical compound NNC(=O)N(N)N BGFGHXUTCFJTLE-UHFFFAOYSA-N 0.000 description 1
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 1
- 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
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-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
- 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
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- WKMJYOVHEKZRTD-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol 2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO WKMJYOVHEKZRTD-UHFFFAOYSA-N 0.000 description 1
- IQQVCMQJDJSRFU-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO IQQVCMQJDJSRFU-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- ROMXEVFSCNLHAB-UHFFFAOYSA-N 2-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC=CC=C1O ROMXEVFSCNLHAB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- WBPXZSIKOVBSAS-UHFFFAOYSA-N 2-tert-butylanthracene Chemical compound C1=CC=CC2=CC3=CC(C(C)(C)C)=CC=C3C=C21 WBPXZSIKOVBSAS-UHFFFAOYSA-N 0.000 description 1
- MWKAGZWJHCTVJY-UHFFFAOYSA-N 3-hydroxyoctadecan-2-one Chemical compound CCCCCCCCCCCCCCCC(O)C(C)=O MWKAGZWJHCTVJY-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- XCKGFJPFEHHHQA-UHFFFAOYSA-N 5-methyl-2-phenyl-4-phenyldiazenyl-4h-pyrazol-3-one Chemical compound CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=CC=C1 XCKGFJPFEHHHQA-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QYGNWDWNZBZHMD-UHFFFAOYSA-N CN(C)C(=NO)C(C1=CC=CC=C1)=O Chemical compound CN(C)C(=NO)C(C1=CC=CC=C1)=O QYGNWDWNZBZHMD-UHFFFAOYSA-N 0.000 description 1
- 241001269524 Dura Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 244000137852 Petrea volubilis Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- MJNIWUJSIGSWKK-UHFFFAOYSA-N Riboflavine 2',3',4',5'-tetrabutanoate Chemical compound CCCC(=O)OCC(OC(=O)CCC)C(OC(=O)CCC)C(OC(=O)CCC)CN1C2=CC(C)=C(C)C=C2N=C2C1=NC(=O)NC2=O MJNIWUJSIGSWKK-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940064734 aminobenzoate Drugs 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- VYVRIXWNTVOIRD-LRHBOZQDSA-N ciguatoxin CTX1B Chemical compound C([C@@]12[C@@H](C)[C@@H]([C@@H]3[C@H]([C@H]([C@H](C)[C@H]4O[C@H]5C[C@@H](C)C[C@H]6O[C@@]7(C)[C@H](O)C[C@H]8O[C@H]9C=C[C@H]%10O[C@H]%11C[C@@H]%12[C@H]([C@@H]([C@H]%13O[C@H](C=CC[C@@H]%13O%12)\C=C\[C@H](O)CO)O)O[C@@H]%11C=C[C@@H]%10O[C@@H]9C\C=C/C[C@@H]8O[C@@H]7C[C@@H]6O[C@@H]5C[C@@H]4O3)O)O2)C)[C@H](O)CO1 VYVRIXWNTVOIRD-LRHBOZQDSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- DYHSMQWCZLNWGO-UHFFFAOYSA-N di(propan-2-yloxy)alumane Chemical compound CC(C)O[AlH]OC(C)C DYHSMQWCZLNWGO-UHFFFAOYSA-N 0.000 description 1
- VLWUKSRKUMIQAX-UHFFFAOYSA-N diethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[SiH](OCC)CCCOCC1CO1 VLWUKSRKUMIQAX-UHFFFAOYSA-N 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MASNVFNHVJIXLL-UHFFFAOYSA-N ethenyl(ethoxy)silicon Chemical compound CCO[Si]C=C MASNVFNHVJIXLL-UHFFFAOYSA-N 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
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 229940048084 pyrophosphate Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 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
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 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 1
- 239000002689 soil 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 229950004616 tribromoethanol Drugs 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Classifications
-
- 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
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- 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)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention provides the manufacture method that can be obtained excellent poly-(methyl) acrylate of the physical characteristics such as adaptation, hardness, chemical proofing, heat resistance and insulating properties by quickly reaction.Obtain the manufacture method of a kind of poly-(methyl) acrylate; it is characterized in that; the monomer composition obtained adding the compound with NCO in the monomer with (methyl) acryloyl group heats, so that the monomer with (methyl) acryloyl group is polymerized at 140 DEG C to 170 DEG C.
Description
Technical field
The present invention relates to the manufacture method of poly-(methyl) acrylate, particularly relate to by isocyanic acid
The monomer with (methyl) acryloyl group is made to occur polymerization to obtain poly-(methyl) propylene in the presence of ester
The manufacture method of acid esters.
And then, poly-(methyl) acrylate of the present invention relates to be obtained by above-mentioned manufacture method, comprise
Its solidification compound, its solidfied material and comprise its printed circuit board (PCB).
Background technology
Poly-(methyl) acrylate (acrylic resin) has high transparent/resistance to impact,
It is prone to thermoplastic shaping/coloring, therefore except being used for building, the vehicles as the substitute of unorganic glass
Window materials etc. outside, also fit as the parts of electric/electronic, commodity, office appliance etc.
For multiple use.
Acrylic resin can utilize irradiation ultraviolet radiation or electricity by adding in (methyl) acrylate
Son bundle isoreactivity energy-ray and produce the free-radical generating agent of free radical and carry out radical polymerization (crosslinking is anti-
Should) manufacture.Alternatively, it is also possible to by adding peroxide in (methyl) acrylate and heating
And the incompatible manufacture of radical polymerization poly-(methyl) acrylate carried out.
As these object lesson, such as, Patent Document 1 discloses and comprise (methyl) acrylate
Ultraviolet-curing resin composition with Photoepolymerizationinitiater initiater.Patent document 1 is recorded by with height
Pressure mercury lamp makes the technological thought that resin solidifies to resin combination irradiation ultraviolet radiation.
And then, patent document 2 is recorded by hindered amine compound and the existence of organic peroxide
The free radical type adhesive composition that lower utilization heating makes (methyl) acrylate carry out solidifying and obtains, makes
(methyl) acrylate below 150 DEG C in a low temperature of solidify.
Additionally, in patent document 3 record, about comprise there is hydroxyl (methyl) acrylate,
Blocked isocyanate, the blend of Photoepolymerizationinitiater initiater, carry out photocuring and heat cure afterwards
Method.
Prior art literature
Patent document
Patent document 1: Japanese Laid-Open Patent Publication 61-31449
Patent document 2: Japanese Unexamined Patent Publication 2008-94913
Patent document 3:2004-513197
Summary of the invention
The problem that invention is to be solved
But, according to patent document 1, utilize optical free radical producing agent to be polymerized, thus react speed
Degree can rise, but curing degree is low.The solidfied material being affected by obtaining may not obtain sufficient adaptation, resistance to
Chemicals.
It addition, the manufacture of the acrylate of patent document 2 employs peroxide.Peroxide is danger
Danger product, the most disposable.
Even if it addition, acrylate also can occur autohemagglutination (homopolymerization) to react by merely heating, but because of
Heat is relatively stablized and is needed to be heated to about more than 200 DEG C by acryloyl group.In this case, not only at energy
There is the leeway of research in efficiency aspect, and as the base material of the object using the composition containing acrylate
Heat resistance also become problem.
And then, in patent document 3, (methyl) acrylate is used as a composition in polymerization, it is necessary to
There is hydroxyl.That is, the hydroxyl of (methyl) acrylate is preferentially carried out with the reaction of isocyanates, and not
The homopolymerization of (methyl) acrylate can occur.
It should be noted that as disclosed in patent document 3, it is known that isocyanates is for manufacturing amino
The raw material of formic acid esters, urea derivative etc., it easily reacts with hydroxyl, amine, phenol, mercaptan etc.,
But apply, entirely without report in reacting about the manufacture at poly-(methyl) acrylate.
While it is true, it is an object of the invention to, it is provided that can by quickly reaction obtain adaptation,
Poly-(methyl) propylene that the physical characteristics such as hardness, chemical proofing, heat resistance and insulating properties are excellent
The manufacture method of acid esters.
And then, it is an object of the invention to, it is provided that the manufacture method of poly-(methyl) acrylate is used
Monomer composition, its solidfied material and comprise its printed circuit board (PCB).
For solving the scheme of problem
In order to solve above-mentioned purpose, the feature of the manufacture method of poly-(methyl) acrylate of the present invention exists
In, by adding in the monomer with (methyl) acryloyl group, there is the compound of NCO and obtain
To monomer composition heat at 140 DEG C to 170 DEG C, so that having (methyl) acryloyl group
Monomer be polymerized.
By the method, adaptation, hardness, chemical proofing, heat resistance and insulation can be produced
Property etc. excellent poly-(methyl) acrylate such as physical characteristic.
And then, in accordance with the invention it is possible to obtain a kind of monomer composition, it is characterised in that comprise made
Poly-(methyl) acrylate made.
This monomer composition is owing to without the functional group reacted at normal temperatures, therefore storage stability is excellent
Different.
The monomer composition of the present invention can by heat cure, photocuring or both and be made into closely sealed
Property, solidfied material (poly-(methyl) acrylic acid that the physical characteristic such as chemical proofing and heat resistance is excellent
Ester), therefore, it is possible to be used as ink or the covering of printed circuit board (PCB) of such as printed circuit board (PCB) printing.
The effect of invention
Manufacturing method according to the invention, it is possible to make that in the presence of isocyanates there is (methyl) propylene
The monomer of acyl group at a lower temperature, carry out homopolymerization in the short time, it is possible to obtain adaptation, hardness,
Poly-(methyl) acrylate that the physical characteristics such as chemical proofing, heat resistance and insulating properties are excellent
Solidfied material or film.
And then, the most there is not polymerisation in the monomer composition of the present invention, therefore, it is possible to a liquid
The form stable ground of type preserves.By monomer composition being coated printed circuit board (PCB) and making it solidify, from
And make the physical characteristic excellences such as adaptation, hardness, chemical proofing, heat resistance and insulating properties
Insulating material for printed circuit board, if adding coloring pigment etc., then can be used for as ink composite
The printing purposes of printed circuit board (PCB).
Accompanying drawing explanation
Fig. 1 is the differential scanning calorimetric curve of the monomer composition illustrating the present invention and the material for comparing
Figure.
Fig. 2 is to illustrate the infrared spectrophotometer when monomer composition of the present invention is heated to different temperatures
The figure of the change of middle absorbance.
Detailed description of the invention
In the present invention, will have the monomer (also referred to as (methyl) acrylate) of (methyl) acryloyl group
With the mixture of isocyanates as monomer composition, by it is entered with the stipulated time at the specified temperature
Row heating, so that the monomer with (methyl) acryloyl group carries out homopolymerization, thus prepares poly-(methyl)
Acrylate.
It addition, the homopolymerization of (methyl) acrylate is generally occurred by the heating of more than 200 DEG C, and this
Invention monomer composition by by it at 140 DEG C～170 DEG C, at preferably 150 DEG C～170 DEG C heat 15
Second～1000 seconds and make (methyl) acrylate contained therein be polymerized.During less than 140 DEG C, (first
Base) polymerization of acrylate becomes insufficient, and during higher than 170 DEG C, have and execute as monomer composition
The substrate giving object produces the dysgenic possibility of calorifics.By at the temperature model of 140 DEG C～170 DEG C
Carrying out 15 seconds～the heating of 1000 seconds in enclosing, the almost all double bond in (methyl) acryloyl group is opened, and becomes
For having the state that the monomer of (methyl) acryloyl group is cross-linked.
Reaction of formation about poly-(methyl) acrylate in the present invention, it is believed that: if at isocyanide
Heat under the state that acid esters and (methyl) acrylate coexist, then the existence of (methyl) acryloyl group promotees
Enter the trimerizing reaction of isocyanates, and the trimerizing of isocyanates reacts, and can produce raising (methyl)
The such result of activity of acryloyl group.
It addition, present invention it is preferred that, having that the monomer of (methyl) acryloyl group do not has can
The functional group reacted with isocyanates.Generally, isocyanates with there is OH, NH2Have Deng to isocyanates
The compound reaction of the hydrogen atom of activity, but not with (methyl) acryloyl group of (methyl) acrylate
React.Therefore, when making (methyl) acrylate react with isocyanates, active hydrogen is used
(methyl) acrylate such as (methyl) acrylate of atom.
But, in order to make the polymerization of (methyl) acrylate preferentially carry out, the method for the present invention or monomer
In composition, and then as other composition, it is also preferred that have can react with isocyanates without any
The compound of functional group.
Furthermore it is possible to think that the heat produced partly by the trimerization reaction of isocyanates also contributes to
The carrying out of (methyl) acrylic ester polymerization.
The film utilizing the product that obtained by the reaction mechanism of the present invention and obtain have high adhesion,
The physical characteristic that chemical proofing, heat resistance etc. are the most excellent, therefore extremely can have in multiple use
Effect ground uses.
It addition, in the trimerization of isocyanates, form the isocyanuric acid ester with triazine ring structure.By comprising
Film that the compound of triazine ring structure is constituted or the heat resistance of solidfied material and insulating properties are excellent, therefore conduct
Heat proof material, insulating materials are useful.
It addition, during more than use trifunctional isocyanates, the network knot with triazine skeleton also can be formed
Structure.Have the material of this network structure have the film improved containing this material or the heat resistance of solidfied material,
The effect of chemical proofing etc..
As it has been described above, the method according to the invention, generate and comprise poly-(methyl) acrylate and isocyanic acid
The reactant mixture of the oligomer such as the tripolymer of ester, this reactant mixture solidifies, thus constitutes closely sealed
Property, film that hardness, chemical proofing, heat resistance and insulating properties are excellent.
[there is the monomer of (methyl) acryloyl group]
The monomer in the present invention, with (methyl) acryloyl group has the (first of more than 1 in 1 molecule
Base) acryloyl group.Can be with isocyanic acid it addition, preferably do not have containing (methyl) acryl monomer
The compound of the functional group of ester reaction.
Herein, it is possible to the functional group reacted with isocyanates refers to the functional group of active hydrogen atom, example
As OH base, NH base, NH can be enumerated2Base, SH base and COOH base.The tool used in the present invention
The monomer having (methyl) acryloyl group does not the most have these functional groups.
(methyl) acrylate used in the present invention such as can enumerate (methyl) acrylic acid 2-(2-
Ethoxy ethoxy) ethyl ester, (methyl) butyl acrylate, (methyl) stearyl acrylate ester, (methyl)
Tridecyl acrylate, (methyl) lauryl acrylate, (methyl) isobornyl acrylate, (first
Base) acrylic acid 2-hydroxy methacrylate, (methyl) acrylic acid 2-hydroxy propyl ester, (methyl) acrylic acid 2-benzene oxygen
Simple function (methyl) acrylate such as base ethyl ester, and multifunctional (methyl) acrylate compounds,
Described multifunctional (methyl) acrylate compounds comprises: 1,3 butylene glycol two (methyl) acrylate,
1,4-butanediol two (methyl) acrylate, 1,6-HD two (methyl) acrylate, diethylene glycol
Two (methyl) acrylate, polyethylene glycol two (methyl) acrylate, polypropylene glycol two (methyl)
Acrylate, Tricyclodecane Dimethanol two (methyl) acrylate, neopentylglycol diacrylate etc. two
Sense (methyl) acrylic acid；The trifunctionals such as trimethylolpropane trimethacrylate (methyl) acrylic acid；
And two trimethylolpropane tetra-acrylate, Dipentaerythritol Pentaacrylate, dipentaerythritol 6 third
(methyl) acrylate more than four senses such as olefin(e) acid ester.
As the ProductName of commercially available (methyl) acrylate compounds, such as, can enumerate NEOMER
DA-600 (Sanyo Chemical Industries, Ltd.'s manufacture), Aronix M-309, M-7100, M309 (east
Sub-synthesis Co., Ltd. manufactures), A-DCP (manufacture of chemical industry Co., Ltd. of Xin Zhong village), 1.6HX-A
(common prosperity chemical industry Co., Ltd. manufacture), FA-125 (Hitachi Chemical Co., Ltd.'s manufacture) etc..
The above-mentioned monomer with (methyl) acryloyl group can be used alone a kind, it is also possible to is applied in combination 2
More than Zhong.
In the present invention, be preferably used multifunctional containing (methyl) acryl monomer, especially trifunctional with
On containing (methyl) acryl monomer, thus, the monomer composition of the present invention is coated substrate etc.
Base material also carries out solidifying and heat resistance, hardness and resistance toization of solidfied material (film after solidification) that obtain
It is the best for learning medicine.
[containing the compound of NCO]
In the present invention, as the compound containing NCO, it is possible to use aliphatic/ester ring type isocyanide
Acid esters, aromatic isocyanate and blocked isocyanate.
Polyfunctional isocyanate is preferably used in the present invention.This is because, when using polyfunctional isocyanate,
Can form the network structure with triazine skeleton, therefore heat resistance, chemical proofing etc. improve further.
This aliphatic/ester ring type isocyanates, aromatic isocyanate compounding amount relative to 100 mass parts
The monomer with (methyl) acryloyl group is 2～100 mass parts, preferably 2～50 mass parts.
It addition, the compounding amount of blocked isocyanate has (methyl) acryloyl group relative to 100 mass parts
Monomer be 2～200 mass parts.During less than 2 mass parts, it is impossible to obtain sufficient Thermocurable, it is impossible to obtain
Obtain adaptation, chemical proofing, heat resistance.During more than 200 mass parts, containing of acryl monomer
Quantitative change is few, ultra-violet solidified difference.
As above-mentioned aliphatic/ester ring type isocyanate compound, such as, have 1,6-hexa-methylene two isocyanic acid
Ester (HDI or HMDI), IPDI (IPDI), hexahydrotoluene 2,4-(2,6)-two are different
Cyanate (hydrogenation TDI), 4,4 '-di-2-ethylhexylphosphine oxide (cyclohexyl isocyanate) (hydrogenation MDI), 1,3-(isocyanide
Acid group closes methyl) hexamethylene (hydrogenation XDI), ENB diisocyanate (NDI), lysine two is different
Cyanate (LDI), trimethyl hexamethylene diisocyanate (TMDI), dimer acid diisocyanate
(DDI), N, N ', N "-three (6-isocyanato-hexa-methylene) biuret etc..
As above-mentioned aromatic isocyanate compound, such as can enumerate toluene di-isocyanate(TDI) (TDI),
4,4 '-methyl diphenylene diisocyanate (MDI), XDI (XDI) etc..
In the present invention, these isocyanates can arbitrarily be used alone one of which, it is possible to use 2 kinds
Above.
In addition it is also possible to use 1, the tripolymer of 6-hexamethylene diisocyanate, isophorone two isocyanide
The tripolymer of acid esters.
It addition, liquefaction and the sight of shelf-life of the monomer composition from the manufacture method of the present invention
Point sets out, and isocyanate compound is preferably used and has carried out end-blocking with known end-capping reagent (sealer)
Blocked isocyanate.
As the ProductName of commercially available blocked isocyanate, such as, can enumerate BI7961, BI7992 (all
Manufacture for Baxenden company), MF-K60X (Asahi Chemical Corp's manufacture), VPLS2253,
BL4265SN (being Sumika Bayer Urethane Co., Ltd. to manufacture) etc..
[end-capping reagent]
As end-capping reagent, such as, can enumerate ethanol, normal propyl alcohol, isopropanol, the tert-butyl alcohol, isobutanol etc.
Alcohols, the phenols such as phenol, chlorophenol, cresols, xylenol, p-nitrophenol, p-t-butyl phenol,
To sec-butyl phenol, to the alkylbenzene phenols such as sec-amyl phenol, POP, nonylphenol, 3-
The basic nitrogen compounds such as pyridone, 8-hydroxyquinoline, 8-hydroxyl quinaldine, diethyl malonate,
Ethyl acetoacetate, acetylacetone,2,4-pentanedione isoreactivity methylene compound, acetamide, acrylamide, acetophenone
The amide-types such as amine, the acid imide such as succimide, maleimide, 2-ethyl imidazol(e), 2-ethyl-4-
The imidazoles such as methylimidazole, pyrazoles, 3-methylpyrazole, 3, the pyrazoles such as 5-dimethyl pyrazole, 2-pyrrolidines
The lactams such as ketone, epsilon-caprolactams, the ketoxime such as acetoxime, methyl ethyl ketoxime, cyclohexanone oxime, acetaldoxime
Or aldoxime class, ethylenimine, bisulfites etc..
As blocked isocyanate, it is preferably with at least appointing in activity methene compound and pyrazoles
Anticipate a kind of end-blocking isocyanates blocked, more preferably with diethyl malonate and 3,5-diformazan
The most any a kind of end-blocking isocyanates blocked in base pyrazoles, particularly preferably with 3,5-
The end-blocking isocyanates that dimethyl pyrazole is blocked.
Above-mentioned end-capping reagent can be used singly or in combination of two or more, it is also possible to uses single
Solely or the multiple blocked isocyanate of two or more blocking agent.
[Photoepolymerizationinitiater initiater]
It addition, the monomer composition used in the present invention can contain Photoepolymerizationinitiater initiater further.As light
Polymerization initiator, as long as can make (methyl) acrylate polymerization occur just by the irradiation of energy-ray
Have no particular limits, it is possible to use radical polymerization initiator.
As optical free radical polymerization initiator, as long as utilize light, laser, electron beam etc. to produce free radical
And cause the compound of Raolical polymerizable, the most all can use.Draw as the polymerization of this optical free radical
Send out agent, such as, can enumerate the benzene such as benzoin, benzoin methylether, benzoin ethyl ether, benzoin iso-propylether
Acyloin and benzoin alkyl ethers；Acetophenone, 2,2-dimethoxy-2-phenyl acetophenone, 2,2-diethoxy
The acetophenones such as base-2-phenyl acetophenone, 1,1-dichloroacetophenone；2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-
Morpholinopropane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butane-1-ketone, N, N-
The aminoacetophenone classes such as dimethylamino benzoylformaldoxime；2-methylanthraquinone, 2-EAQ, 2-tert-butyl anthracene
The Anthraquinones such as quinone, 1-chloroanthraquinone；2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, CTX,
The thioxanthene ketones such as 2,4-diisopropylthioxanthone；Acetophenone dimethyl ketal, benzil dimethyl ketal etc.
Ketal class；2,4,5-triarylimidazoles dimer；Hibon；2-mercaptobenzimidazole, 2-sulfydryl
The mercaptan compound such as benzothiazole, 2-mercaptobenzothiazole；2,4,6-tri--s-triazine, 2,2,2-ethobrom,
The organohalogen compounds such as trisbromomethyl benzene sulfone；Benzophenone, 4,4 '-bis-diethylamino benzophenone etc.
Benzophenone or xanthones；2,4,6-trimethyl benzoyl diphenyl base phosphine oxide etc..
Above-mentioned optical free radical polymerization initiator can be used alone or mix multiple use.
It addition, in addition, it is also possible to use N, N-dimethyl amino benzoate, N, N-dimethyl
The tertiary amines such as aminobenzoic isoamyl valerate, 4-dimethylaminobenzoic acid pentyl ester, triethylamine, triethanolamine
Etc. light-initiated auxiliary agent.It addition, in order to promote light reaction, it is also possible to add in optical free radical polymerization initiator
The titanocenes of (BASF JAPAN LTD. manufactures) such as the CGI-784 having absorption in being added in visible region
Compound etc..It should be noted that the composition being added in optical free radical polymerization initiator is not limited to above-mentioned,
As long as absorbing light in ultraviolet light or visible region, and the unsaturated groups such as (methyl) acryloyl group are made to enter
Row radical polymerization, then be not limited to Photoepolymerizationinitiater initiater, light-initiated auxiliary agent, can be used alone or in combination
Multiple use.
The compounding amount of Photoepolymerizationinitiater initiater has the monomer of (methyl) acryloyl group relative to 100 mass parts
It is 0.5～15 mass parts, more preferably 0.5～10 mass parts, it is further preferred that 1～10 mass parts.
As the ProductName of commercially available Photoepolymerizationinitiater initiater, such as can enumerate Irgacure907,
Irgacure127 (being BASF JAPAN LTD. to manufacture) etc..
[other additive]
In the monomer composition of the present invention, froth breaking/levelling agent, thixotropy conferring agents can be contained as required
The additives such as/thickener, coupling agent, dispersant, fire retardant.
As defoamer/levelling agent, it is possible to use organosilicon, modified organic silicon, mineral oil, vegetable oil,
Aliphatic alcohol, aliphatic acid, metallic soap, fatty acid amide, polyether polyols, polyoxy alkylidene alkane
The compounds etc. such as base ether, polyoxyalkylene fatty acid esters.
As thixotropy conferring agents/thickener, it is possible to use kaolin, montmorillonite (smectite), illiteracy are de-
Viscosity mineral or the particulate titanium dioxide such as soil (montmorillonite), bentonite, talcum, mica, zeolite
Silicon, silica gel, amorphous inorganic particle, polyamide-based additive, modified urea system additive, wax system add
Agent etc..
By adding froth breaking/levelling agent, thixotropy conferring agents/thickener, it is possible to special to the surface of solidfied material
The proterties of property and composition is adjusted.
About coupling agent, it is possible to use: as alkoxyl have methoxyl group, ethyoxyl, acetyl group etc. and
As reactive functional groups, there is vinyl, methylacryloyl, acryloyl group, epoxy radicals, cyclic rings
The silane of epoxide, sulfydryl, amino, diaminourea, acid anhydrides, uride base, thioether group, NCO etc.
Coupling agent, the most such as vinylethoxysilane, vinyltrimethoxy silane, vinyl three (β-first
Epoxide ethyoxyl) the ethene base system silanization such as silane, γ-methacryloxypropyl trimethoxy silane
Compound, gamma-amino propyl trimethoxy silicane, N-β-(amino-ethyl) gamma-amino propyl trimethoxy silicon
Alkane, N-β-(amino-ethyl) gamma-amino hydroxypropyl methyl dimethoxysilane, γ-ureido-propyl triethoxy
The amino system silane compounds such as silane, γ-glycidoxypropyltrime,hoxysilane, β-(3,4-epoxide ring
Hexyl) the epoxy silicon such as ethyl trimethoxy silane, γ-glycidoxypropyl diethoxy silane
The sulfydryl such as hydride compounds, γ mercaptopropyitrimethoxy silane system silane compound, Ν-phenyl-gamma-amino third
The silane couplers such as phenylamino base system silane compound such as base trimethoxy silane；Isopropyl three isostearoyl
Change titanate esters, four octyl groups double (two-tridecyl phosphite) titanate esters, double (dioctylphyrophosphoric acid
Ester) ethoxyacetic acid ester titanate esters, isopropyl three-dodecyl benzenesulfonyl titanate esters, isopropyl three (two
Octyl group pyrophosphate) titanate esters, tetra isopropyl double (dioctyl phosphito ester) titanate esters, four (1,1-
Diene propoxy methyl-1-butyl)-bis-(two-tridecyl) phosphite ester titanate esters, double (dioctyl
Pyrophosphoric acid ester group) ethylene titanate esters, isopropyl three caprylyl titanate esters, isopropyl Dimethylacryloyl
Isostearoyl base titanate esters, isopropyl three stearyl two acryloyl group titanate esters, (two is pungent for isopropyl three
Base phosphate) titanate esters, isopropyl three cumyl phenyl titanate esters, dicumylphenyl ethoxyacetic acid ester metatitanic acid
The titanate esters system coupling agents such as ester, two isostearoyl base ethylidene titanate esters；Containing olefinic unsaturation zirconate
Compound, the compound containing new alkoxy zirconium ester, the new trineodecanoyl zirconate of new alkoxyl three, new alcoxyl
Base three (dodecyl) benzenesulfonyl zirconate, new alkoxyl three (dioctyl) Zirconium phosphoester acid esters,
New alkoxyl three (dioctyl) pyrophosphate zirconate, new alkoxyl three (ethylene amino) ethyl
Zirconate, new alkoxyl three (amino) phenyl zirconate, four (2,2-diene propoxy methyl) fourth
Base-two (two-tridecyl) phosphite ester zirconate, the new caprinoyl of neopentyl (diallyl) epoxide-three
Base zirconate, neopentyl (diallyl) epoxide-three (dodecyl) benzenesulfonyl zirconate, new
Amyl group (diallyl) epoxide-three (dioctyl) Zirconium phosphoester acid esters, neopentyl (diallyl)
Epoxide-three (dioctyl) pyrophosphate zirconate, neopentyl (diallyl) epoxide-three (N-Asia second
Base diaminourea) ethyl zirconate, neopentyl (diallyl) epoxide-three (amino) phenyl zirconic acid
Ester, neopentyl (diallyl) epoxide-trimethacrylate acyl group zirconate, neopentyl (diallyl)
Epoxide-triacryl zirconate, di neo-pentyl (diallyl) epoxide-two p-benzoyl base zirconium
Double (the 2-third of acid esters, di neo-pentyl (diallyl) epoxide-two (3-sulfydryl) propionic acid zirconate, 2,2-
Enol closes methyl) butanol base-ring two [2,2-(double 2-propenyls close methyl) butanol base] pyrophosphate-O, O-
Zirconium (IV) (Zirconium IV 2,2-bis (2-propenolatomethyl) butanolato, cyclo-di-[2,2-
(bis2-propenolatomethyl) butanolato] pyrophosphate-O, O) etc. zirconate system coupling agent；
The Aluminates such as diisobutyl (oil base) acetoacetyl aluminate, Acetacetic acid alkyl ester aluminum-diisopropoxide
It it is coupling agent etc..
As dispersant, it is possible to use polycarboxylic-acid, naphthalenesulfonic acid formalin condensation system, polyethylene glycol,
The high-molecular type dispersing agents such as polycarboxylic acids part Arrcostab system, polyethers system, polyalkylene polyamine system, alkyl sulphur
The low molecule type dispersions such as acid system, quaternary ammonium system, higher alcohol epoxy methane series, polyol ester system, alkylated polyamines system
Agent etc..
As fire retardant, it is possible to use the hydrated metal such as aluminium hydroxide, magnesium hydroxide system, red phosphorus, phosphoric acid
Ammonium, ammonium carbonate, Firebrake ZB, zinc stannate, molybdenum compound system, bromine compounds system, chlorine compound system, phosphorus
Acid esters, phosphorus-containing polyol, containing phosphamidon, cyanurate melamine, melamine compound, triazine chemical combination
Thing, guanidine compound, organosilicon polymer etc..
And then, organic Binder Composition can be added in the monomer composition of the present invention.It addition, for adjusting
Whole polymerization speed, the degree of polymerization, it is possible to add polymerization inhibitor, retarder.
Can be to be colored as purpose interpolation coloring pigment, dyestuff etc. in the monomer composition of the present invention.Make
For coloring pigment, dyestuff etc., can use in order to lower pigment concordance list show known in usual coloring pigment,
Dyestuff.
Such as can enumerate pigment blue 15,15:1,15:2,15:3,15:4,15:6,16,60, solvent
Blue 35,63,68,70,83,87,94,97,122,136,67,70, pigment Green 7,36,3,
5,20,28, solvent yellow 16 3, pigment yellow 24,108,193,147,199,202,110,109,
139、179、185、93、94、95、128、155、166、180、120、151、154、156、
175、181、1、2、3、4、5、6、9、10、12、61、62、62:1、65、73、74、75、
97、100、104、105、111、116、167、168、169、182、183、12、13、14、
16、17、55、63、81、83、87、126、127、152、170、172、174、176、188、
198, pigment orange 1,5,13,14,16,17,24,34,36,38,40,43,46,49,
51,61,63,64,71,73, paratonere 1,2,3,4,5,6,8,9,12,14,15,
16、17、21、22、23、31、32、112、114、146、147、151、170、184、187、
188、193、210、245、253、258、266、267、268、269、37、38、41、48:1、
48:2、48:3、48:4、49:1、49:2、50:1、52:1、52:2、53:1、53:2、57:1、58:4、
63:1、63:2、64:1、68、171、175、176、185、208、123、149、166、178、
179、190、194、224、254、255、264、270、272、220、144、166、214、
220,221,242,168,177,216,122,202,206,207,209, solvent of red 135,
179,149,150,52,207, pigment violet 19,23,29,32,36,38,42, solvent violet 13,
36, pigment brown 23,25, pigment black 1,7 etc..These coloring pigment dyestuffs etc. are relative to 100 mass parts
Monomer composition preferably adds 0.01～5 mass parts.It addition, be used for marking by the monomer composition of the present invention
In the case of purposes, preferably add the titanium oxide of rutile-type, Detitanium-ore-type for guaranteeing visibility.This
In the case of Zhong, relative to 100 mass parts monomer compositions, preferably add 1～20 mass parts.These colorings
Pigment/dyes etc. can be used alone or in combination two or more and use.
And then, in the monomer composition of the present invention, it is possible to use for adjusting the solvent of viscosity, but be
Preventing the thickness after solidification from reducing, addition is preferred less.It addition, more preferably do not contain for adjusting
The solvent of viscosity.
When the monomer composition of the present invention contains Photoepolymerizationinitiater initiater, by irradiation ultraviolet radiation, electron beam,
Chemical ray isoreactivity energy-ray, makes (methyl) acrylate carry out photocuring, thereafter, by such as
Heat described on, (methyl) acrylate can be made to be polymerized.
Therefore, make to coat the monomer composition of the base materials such as substrate by the photocuring irradiated based on light, with
And ensuing heat cure the two stage based on heating and solidify, workability and said curing
General each characteristic of thing improves.
In the present invention, when monomer composition is fully cured, it is possible to use known heater means, the hottest
The heating furnaces such as wind furnace, electric furnace, infrared induction heating furnace.
The transparency of poly-(methyl) acrylate that manufactured by the manufacture method of the present invention, plasticity, resistance to
The excellences such as impact, adaptation, chemical proofing, heat resistance and insulating properties, therefore can be suitably used for many
Plant purposes.Such as, in addition to window materials for the vehicles such as building, vehicle etc., also can fit
For electric/electronic, commodity, office appliance etc., particularly preferred for needs resistance to impact, close
Conjunction property, chemical proofing, heat resistance and the product such as printed circuit board (PCB) of insulating properties.
It should be noted that the present invention is not limited to technical scheme and the enforcement of above-mentioned embodiment
Example, can carry out various deformation in the range of the main idea of invention.
Embodiment
I. hot set test
[embodiment 1～11 and comparative example 1～4]
Each composition is compounded in the ratio shown in table 1, it is obtained the present invention's with dissolvers stirring
Monomer composition and compare monomer composition.
[gel time mensuration]
For the monomer composition of the present invention, (day, new science Co., Ltd. manufactured to use gelation testing machine
Gelation testing machine), heat the most at an established temperature, measure until gelation
Till time.By result record in Table 1.
[table 1]
The compounding amount of each material in table is in units of mass parts.
Gel time refers to lose flowability to material from beginning to warm up monomer composition and solidifies
Time (measured by gelation testing machine, in seconds).
It should be noted that the details of material described in table 1 is as follows.
Acrylate 1: trimethylolpropane trimethacrylate (TMPTA)
Toagosei Co., Ltd manufactures M-309
Acrylate 2: Tricyclodecane Dimethanol diacrylate
KCC of Xin Zhong village manufactures A-DCP
Acrylate 3:1,6-hexanediyl ester
Kyoeisha Chemical Co., Ltd. manufactures 1.6HX-a
Acrylate 4: neopentylglycol diacrylate
Hitachi Chemical Co., Ltd. manufactures FA-125M
Isocyanates 1 a: xylylene diisocyanate
Isocyanates 2: IPDI
Isocyanates 3:1,6-hexamethylene diisocyanate
Blocked isocyanate 1:Baxenden company manufacture BI7961
Solid constituent 70% NCO composition 10.2%
The biuret body dimethylpyrazole of 1,6-hexamethylene diisocyanate
Material
Blocked isocyanate 2:Baxenden company manufacture BI7992
Solid constituent 70% NCO composition 9.2%
The tripolymer dimethyl pyrazole of 1,6-hexamethylene diisocyanate and (activity methene compound)
The material of diethyl malonate end-blocking
Blocked isocyanate 3: Asahi Chemical Corp manufactures MF-K60X
Solid constituent 60% NCO composition 6.6%
The material of 1,6-hexamethylene diisocyanate activity methene compound end-blocking
Blocked isocyanate 4:Sumika Bayer Urethane Co., Ltd. manufactures VPLS2253
Solid constituent 75% NCO composition 10.5%
The material of the tripolymer dimethylpyrazole of 1,6-hexamethylene diisocyanate
Blocked isocyanate 5:Sumika Bayer Urethane Co., Ltd. manufactures BL4265SN
Solid constituent 65% NCO composition 8.1%
The material that the tripolymer of IPDI is blocked by methyl ethyl ketoxime
By measuring gel time, for the composition of embodiment 1～8, the feelings carried out at 150 DEG C
Under condition, 21 seconds used times～complete the polymerization of acrylate for 590 seconds.
On the other hand, in the comparative example 1 without isocyanates, even if carrying out the test of more than 1000 seconds,
The most there is not gelation.
It addition, in the composition of embodiment 9～11, maximum with generation gelation in 926 seconds, polymerisation
Complete.On the other hand, in comparative example 2～4, though the test of longer more than 2000 seconds of the time of carrying out,
The most there is not gelation.It follows that under the acryloyl group the coexisting with isocyanates, i.e. can under low temperature
React, but do not react when there is not isocyanates.
[mensuration of DSC data]
About embodiment 1 and the composition of comparative example 1, Seiko Electronics Co., Ltd is used to manufacture
EXSTAR, carries out means of differential scanning calorimetry mensuration (DSC).The DSC curve obtained is shown in Fig. 1.
Its result understands: with the exothermic peak phase of the simple trimethylolpropane trimethacrylate of comparative example 1
Ratio, the trimethylolpropane trimethacrylate of embodiment 1 and an isocyanates (xyxylene two isocyanic acid
Ester) the exothermic peak of composition move to low temperature side, it can solidify at low temperatures.
This DSC measurement result illustrates the peak of the polymerization produced in embodiment 1 and comparative example 1 indirectly, its
Consistent with above-mentioned gel time measurement result, therefore it can be concluded that occurred by gelation
The polymerization of acrylate.
[mensuration of ir spectrophotometry]
For the composition of embodiment 1, use the Spectrum100 that Perkin Elmer Japan Ltd. manufactures,
Absorbance (absorption) is measured by infrared spectrophotometer (IR Spectroscopy).Need
Bright, as MacroATR unit, employ smiths Dura Sampl IRII.
This mensuration is carried out for following sample: first, is coated with by the composition of embodiment 1 with scraper
On 2 KBr plates, by wherein one in atmosphere with 30 minutes (sample 1) of 80 DEG C of heating, by another
In atmosphere with 30 minutes (sample 2) of 150 DEG C of heating.
The IR spectrogram recording sample 1 illustrates above Fig. 2, and the IR spectrogram recording sample 2 exists
The lower section of Fig. 2 illustrates.
Sample 1, compared with the IR spectrogram of sample 2, represents the 2260cm of NCO-1Neighbouring peak exists
In the collection of illustrative plates of sample 1 (80 DEG C of heating) substantially, significantly subtract in the collection of illustrative plates of sample 2 (150 DEG C of heating)
Few.
And then, represent the 1406cm of acryloyl group-1Neighbouring peak is in the collection of illustrative plates of sample 1 (80 DEG C of heating)
Substantially, it is greatly decreased in the collection of illustrative plates of sample 2 (150 DEG C of heating).
It follows that isocyanates is consumed under heating with acryloyl group.
Additionally it is observed that compared with sample 1 (80 DEG C of heating), 1721cm-1The peak of neighbouring carbonyl
Sample 2 (150 DEG C of heating) increases.
This shows that NCO generation trimerization generates carbonyl.
Measurement result shown in integrated survey Fig. 1 and Fig. 2, it may be said that by isocyanates and propylene
Heat under the coexisting state of acid esters, thus the trimerization of isocyanates occurs, with the reaction phase of this trimerization
Companion, there occurs the polymerization of acrylate.
II. photo-thermal use solidity test
[embodiment 12,13, and comparative example 5]
1. ultraviolet irradiation process
In the ratio shown in table 2, each composition is compounded, it is obtained this with dissolvers stirring
Bright monomer composition and compare monomer composition.
[table 2]
| Embodiment 12 | Embodiment 13 | Comparative example 5 | |
| Acrylate 1 | 60 | 60 | 60 |
| Photoepolymerizationinitiater initiater 1 | 3 | 3 | 3 |
| Photoepolymerizationinitiater initiater 2 | 3 | 3 | 3 |
| Isocyanates 1 | 10 | - | - |
| Blocked isocyanate 2 | - | 60 | - |
| Levelling agent | 0.1 | 0.1 | 0.1 |
It should be noted that the details of material described in table 2 is as follows.
Acrylate 1: trimethylolpropane trimethacrylate (TMPTA)
Toagosei Co., Ltd manufactures M-309
Photoepolymerizationinitiater initiater 1:BASF JAPAN LTD. manufactures Irgacure907
Photoepolymerizationinitiater initiater 2:BASF JAPAN LTD. manufactures Irgacure127
Isocyanates 1 a: xylylene diisocyanate
Blocked isocyanate 2:Baxenden company manufacture BI7992
Solid constituent 70%NCO composition 9.2% (1,6-hexamethylene diisocyanate active methylene group
The material of compound end-blocking)
Levelling agent: BYK JAPAN LTD. manufactures BYK-307
[making of test sample]
A. ultraviolet irradiation sample: FR-4/10 μ
The following uncured sample making several each tests: by monomer composition and the ratio of the present invention
Relatively monomer composition is on the FR-4 copper-clad laminated board (substrate) of 150mm × 95mm × 1.6mm, logical
Cross bar coater to be coated in the way of thickness reaches 10 μm, thus make uncured sample.To these
Uncured sample high voltage mercury lamp radiation accumulated light is 150mJ/cm2Ultraviolet.
Under carrying out for each sample (ultraviolet irradiation sample: FR-4/10 μ) after ultraviolet irradiation process
State fitness test, pencil hardness test, chemical proofing test, heat resistant test.By result of the test
Record is in table 3.
B. ultraviolet irradiates/heats sample: FR-4/10 μ
Utilize heated air circulation type drying oven that ultraviolet irradiates sample: FR-4/10 μ heats 30 at 150 DEG C
Minute, obtain ultraviolet irradiate/heating after sample (ultraviolet irradiate/heat sample: FR-4/10 μ).
This sample is carried out following fitness test, pencil hardness test, chemical proofing test and heat-resisting
Test.By logging in table 4.
C. ultraviolet irradiates/heats sample: B COUPON/40 μ
By the monomer composition of the present invention and compare monomer composition and be applied to IPC with thickness 40 μm
On comb-type electrode B COUPON (substrate) of B-25 test pattern, carry out ultraviolet same as described above
Irradiate, then carry out heating same as described above, thus obtain the sample that ultraviolet irradiates/heats: B
COUPON/40μ.It is carried out following insulating properties test.
Above-mentioned each sample is carried out attribute testing shown below.
[1. fitness test]
Film coated surface cutter in each sample cut 11 joint-cuttings with 1mm interval, in length and breadth by film
Paste adhesive tape on 100 cutting zones that the joint-cutting in length and breadth on surface surrounds, peel off, check not
Peeled off by adhesive tape and residue in the number of the cutting zone of the film of FR-4.
[2. pencil hardness test]
Make each sample, carry out according to JISK5400, the Hi-uni using Mitsubishi Pencil K. K to manufacture
The mensuration of pencil hardness test.
Specifically, cutting the timber portion of pencil, exposed length is the pen core of 5～6mm.Use
Pen core front end is ground to smooth at sand paper and forms the pencil of circular cross-section.By this pencil with sample table
Face is that the angle of 45 degree keeps, and applies the load of 1kg, with the angles of 45 degree at film on sample surfaces
On scratch.By the highest hardness record of non-for film scratch to the pencil of substrate in table 2.
[3. chemical proofing test]
Make each sample impregnate 30 minutes under room temperature in the aqueous sulfuric acid of 10%, after being drawn off, carry out water
Wash, be dried.After the painting membrane stage of dried each sample is carried out visual valuation, with Cellotape (note
Volume trade mark) peel off, it is carried out as follows evaluation.
Zero: the state of film is entirely without change.
×: film has and floats, peels off.Or, exist and be significantly transferred to Cellotape (registration mark)
Stripping.
[4. heat resistant test]
Each sample is coated with rosin series scaling powder (SF-270 that Sanwa Chemical Co., Ltd manufactures),
The solder bath of 260 DEG C impregnates 10 seconds.After each sample being taken out from solder bath and naturally cooling down, use
Propylene glycol methyl ether acetate washs, is dried.Painting after this test repeats 3 times, to each test film
After the state of film carries out visual valuation, peel off with Cellotape (registration mark), be carried out as follows
Evaluate.
Zero: the state of film is entirely without change.
△: be visually not changed in, has some strippings when peeling off with Cellotape (registration mark).
×: film has and floats, peels off.Or, exist and be significantly transferred to Cellotape (registration mark)
Stripping.
[5. insulating properties test]
For aforesaid ultraviolet irradiation sample: B COUPON/40 μ, apply the bias of DC500V,
Measure insulating resistance value.It is carried out as follows evaluation.
Zero: insulating resistance value >=100G Ω
×: insulating resistance value < 100G Ω
A. ultraviolet irradiation sample: the result of the test of FR-4/10 μ
(chemical proofing is tested, and heat-resistance test for fitness test, pencil hardness test)
[table 3]
| Embodiment 12 | Embodiment 13 | Comparative example 5 | |
| 1. fitness test | 0/100 | 0/100 | 0/100 |
| 2. pencil hardness test | H | H | H |
| 3. chemical proofing test | × | × | × |
| 4. heat-resistance test | × | × | × |
B. ultraviolet irradiates/heats sample: the result of the test of FR-4/10 μ
(fitness test, pencil hardness test, chemical proofing are tested and heat-resisting
Property test)
C. ultraviolet irradiates/heats sample: the result of the test (insulating properties test) of B COUPON/40 μ
[table 4]
| Embodiment 12 | Embodiment 13 | Comparative example 5 | |
| 1. fitness test | 100/100 | 100/100 | 0/100 |
| 2. pencil hardness test | 5H | 3H | H |
| 3. chemical proofing test | ○ | ○ | × |
| 4. heat-resistance test | ○ | ○ | × |
| 5. insulating properties test | ○ | ○ | - |
-: do not evaluate
According to above-mentioned table 4 it will be apparent that, the film obtained by the manufacture method of the present invention/solidfied material tool
There is the performance that adaptation, hardness, chemical proofing, heat resistance and insulating properties are all excellent.
It should be noted that the present invention is not limited to technical scheme and the embodiment of above-mentioned embodiment,
Various deformation can be carried out in the range of invention main idea.
Claims (6)
1. the manufacture method of poly-(methyl) acrylate, it is characterised in that will be to having (methyl)
The monomer of acryloyl group adds the monomer composition having the compound of NCO and obtain exist
Heat at 140 DEG C to 170 DEG C so that described in there is (the first of monomer of (methyl) acryloyl group
Base) acryloyl group is polymerized, described in have that the monomer of (methyl) acryloyl group do not has can be with different
The functional group of polyisocyanate reactant.
Manufacture method the most according to claim 1, it is characterised in that also to described monomer composition
Middle interpolation Photoepolymerizationinitiater initiater, irradiate active energy beam so that described in there is (methyl) acryloyl
The monomer of base carries out photocuring, then by described heating make described in there is the list of (methyl) acryloyl group
Body is polymerized.
3. poly-(methyl) acrylate, it is characterised in that it is by claim 1 or 2
Described manufacture method obtains.
4. a monomer composition, it is characterised in that it is for the manufacture method described in claim 1.
5. a solidfied material, it is characterised in that it is to make the monomer composition described in claim 4 solidify
?.
6. a printed circuit board (PCB), it is characterised in that it has the solidfied material described in claim 5.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012081942 | 2012-03-30 | ||
| JP2012-081942 | 2012-03-30 | ||
| PCT/JP2013/058634 WO2013146705A1 (en) | 2012-03-30 | 2013-03-25 | Production method of poly(meth)acrylate, poly(meth)acrylate obtained thereby, monomer composition, cured product thereof, and printed wiring board containing same. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104203992A CN104203992A (en) | 2014-12-10 |
| CN104203992B true CN104203992B (en) | 2016-08-24 |
Family
ID=49259956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380017235.5A Active CN104203992B (en) | 2012-03-30 | 2013-03-25 | Poly-(methyl) acrylate and manufacture method, monomer composition, solidfied material and printed circuit board (PCB) |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6259394B2 (en) |
| KR (1) | KR102000325B1 (en) |
| CN (1) | CN104203992B (en) |
| TW (1) | TWI588163B (en) |
| WO (1) | WO2013146705A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3147303A1 (en) * | 2015-09-25 | 2017-03-29 | Ernesto Monton Martin | Solid surface product comprising aliphatic isocyanate and process for manufacturing thereof |
| CN112063209A (en) * | 2020-08-31 | 2020-12-11 | 岳刚 | Photo-polymerization method for synthesizing photo-curing acrylate PCB protective coating |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4117235A (en) * | 1971-09-23 | 1978-09-26 | Owens-Illinois, Inc. | Novel preparation of novel low molecular weight, liquid polymer |
| CN1535289A (en) * | 2000-11-06 | 2004-10-06 | Method for coating substrates | |
| CN101563382A (en) * | 2006-12-19 | 2009-10-21 | 巴斯福涂料股份公司 | Coating agents having high scratch resistance and weathering stability |
| CN102066433A (en) * | 2008-06-17 | 2011-05-18 | 阿克马法国公司 | Composition containing (meth)acrylic polymer and copolymer having associative groups |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6131449A (en) | 1984-07-23 | 1986-02-13 | Nippon Kayaku Co Ltd | Ultraviolet-curing resin composition |
| JP2002174892A (en) * | 2000-12-07 | 2002-06-21 | Hitachi Chem Co Ltd | Photosensitive resin composition, photosensitive element, method for producing resist pattern and method for producing printed wiring board |
| JP2008094913A (en) | 2006-10-10 | 2008-04-24 | Toray Fine Chemicals Co Ltd | One-component radically curable adhesive composition |
| US8178204B2 (en) * | 2008-03-05 | 2012-05-15 | Bayer Materialscience Llc | Acrylate-modified aspartates and gel coat compositions made therefrom |
| JP5422195B2 (en) * | 2008-12-18 | 2014-02-19 | リンテック株式会社 | Release agent and release sheet |
| JP2010212516A (en) * | 2009-03-11 | 2010-09-24 | Mitsubishi Paper Mills Ltd | Crosslinking composition for manufacturing screen printing mask with resin |
| CN102666971B (en) * | 2009-11-20 | 2014-12-17 | 大金工业株式会社 | Fluoropolymers and treatment agent |
| DE102009055061A1 (en) * | 2009-12-21 | 2011-06-22 | Evonik Degussa GmbH, 45128 | New initiation procedure for the polymerization of (meth) acrylates |
| KR20130124359A (en) * | 2011-01-27 | 2013-11-13 | 가부시키가이샤 오토네트웍스 테크놀로지스 | Chain transfer agent, photosensitive composition, cured product of photosensitive composition, and method for curing photosensitive composition |
| JP5802396B2 (en) * | 2011-01-27 | 2015-10-28 | 株式会社オートネットワーク技術研究所 | Ultraviolet curable composition and cured product using the same |
-
2013
- 2013-03-25 CN CN201380017235.5A patent/CN104203992B/en active Active
- 2013-03-25 WO PCT/JP2013/058634 patent/WO2013146705A1/en active Application Filing
- 2013-03-25 JP JP2014507875A patent/JP6259394B2/en active Active
- 2013-03-25 KR KR1020147025253A patent/KR102000325B1/en active IP Right Grant
- 2013-03-29 TW TW102111526A patent/TWI588163B/en active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4117235A (en) * | 1971-09-23 | 1978-09-26 | Owens-Illinois, Inc. | Novel preparation of novel low molecular weight, liquid polymer |
| CN1535289A (en) * | 2000-11-06 | 2004-10-06 | Method for coating substrates | |
| CN101563382A (en) * | 2006-12-19 | 2009-10-21 | 巴斯福涂料股份公司 | Coating agents having high scratch resistance and weathering stability |
| CN102066433A (en) * | 2008-06-17 | 2011-05-18 | 阿克马法国公司 | Composition containing (meth)acrylic polymer and copolymer having associative groups |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6259394B2 (en) | 2018-01-10 |
| TW201348270A (en) | 2013-12-01 |
| WO2013146705A1 (en) | 2013-10-03 |
| JPWO2013146705A1 (en) | 2015-12-14 |
| TWI588163B (en) | 2017-06-21 |
| CN104203992A (en) | 2014-12-10 |
| KR20140138706A (en) | 2014-12-04 |
| KR102000325B1 (en) | 2019-07-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104204112B (en) | Photosetting and thermosetting composition, the manufacture method of its solidfied material, solidfied material and the printed circuit board (PCB) with it | |
| CN101402775B (en) | Inorganic filler and organic filler-containing curable resin composition, resist film coated printed wiring board, and method for producing the same | |
| CN109476077B (en) | Method and composition for forming three-dimensional objects by additive fabrication | |
| CN103756550B (en) | The preparation method of the hybridized aqueous anti-icing paint of a kind of one pack system and coating thereof and application | |
| CN102171265B (en) | Curable resin composition and paint, and plastic molded product produced by laminating the same | |
| JPWO2018012014A1 (en) | Bright pigment dispersion | |
| CN101675089A (en) | (meth)acrylate compound, resin composition containing the same, cured product of the resin composition, and energy ray-curable resin composition for optical lens sheet and cured product thereof | |
| CN104974594A (en) | Printing ink composition with water-soluble solvent, application of printing ink composition, and printed circuit board | |
| CN112313297B (en) | Aqueous coating composition and method for producing aqueous coating composition | |
| CN110204685B (en) | Tri-functionality polyurethane acrylate resin and preparation method and application thereof | |
| CN106995655A (en) | No-solvent type UV cure coating compositions and coating | |
| JP5944608B1 (en) | Resin composition for coating | |
| CN104203992B (en) | Poly-(methyl) acrylate and manufacture method, monomer composition, solidfied material and printed circuit board (PCB) | |
| CN109852136A (en) | One-component ink and water-based ink coating for 3C glass | |
| JP2008528771A (en) | Poly (meth) acrylates modified with reactive ethylene groups and uses thereof | |
| KR102419825B1 (en) | Paint Composition | |
| CN111902295B (en) | Printed matter | |
| CN107847969A (en) | The method for preparing the coating being made up of priming paint and finish paint | |
| JP4288691B2 (en) | Method for producing cured coating film using paint containing photocurable resin composition | |
| CN113698862B (en) | Water-based paint and preparation method and application thereof | |
| CN110922603B (en) | Photocuring resin modified by different chain segments and preparation method and application thereof | |
| JP4880413B2 (en) | Water-based paint composition for plastics | |
| JP2001011140A (en) | Photocurable resin composition and coating material | |
| CN109852115A (en) | A kind of LED-UV photocuring solventless varnish | |
| CN109825118A (en) | A kind of solvent-free white paint of LED-UV photocuring |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |