JP5883387B2 - 電気、電子部品材料用組成物およびその硬化物 - Google Patents
電気、電子部品材料用組成物およびその硬化物 Download PDFInfo
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- JP5883387B2 JP5883387B2 JP2012531673A JP2012531673A JP5883387B2 JP 5883387 B2 JP5883387 B2 JP 5883387B2 JP 2012531673 A JP2012531673 A JP 2012531673A JP 2012531673 A JP2012531673 A JP 2012531673A JP 5883387 B2 JP5883387 B2 JP 5883387B2
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- 239000000203 mixture Substances 0.000 title claims description 68
- 239000000463 material Substances 0.000 title claims description 57
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 144
- 239000000178 monomer Substances 0.000 claims description 79
- 229920002554 vinyl polymer Polymers 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 239000003999 initiator Substances 0.000 claims description 40
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 34
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 34
- 125000000962 organic group Chemical group 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000005227 gel permeation chromatography Methods 0.000 claims description 12
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 230000005611 electricity Effects 0.000 claims description 3
- -1 isooctyl Chemical group 0.000 description 64
- 239000000047 product Substances 0.000 description 37
- 238000000034 method Methods 0.000 description 36
- 238000001723 curing Methods 0.000 description 28
- 238000002845 discoloration Methods 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 20
- 238000010521 absorption reaction Methods 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000012856 packing Methods 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 239000003963 antioxidant agent Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 238000009413 insulation Methods 0.000 description 11
- 239000003505 polymerization initiator Substances 0.000 description 11
- 238000010526 radical polymerization reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 238000010292 electrical insulation Methods 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000002739 metals Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000012719 thermal polymerization Methods 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 239000012966 redox initiator Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 7
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 7
- 239000004925 Acrylic resin Substances 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000004382 potting Methods 0.000 description 5
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 4
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 4
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 description 4
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical group C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 3
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 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 3
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- VMFJVWPCRCAWBS-UHFFFAOYSA-N (3-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 VMFJVWPCRCAWBS-UHFFFAOYSA-N 0.000 description 2
- ZRIPJJWYODJTLH-UHFFFAOYSA-N (4-benzylphenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 ZRIPJJWYODJTLH-UHFFFAOYSA-N 0.000 description 2
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- JYAQYXOVOHJRCS-UHFFFAOYSA-N 1-(3-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=C1 JYAQYXOVOHJRCS-UHFFFAOYSA-N 0.000 description 2
- HDMHXSCNTJQYOS-UHFFFAOYSA-N 1-(4-prop-2-enylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(CC=C)C=C1 HDMHXSCNTJQYOS-UHFFFAOYSA-N 0.000 description 2
- STFXXRRQKFUYEU-UHFFFAOYSA-N 16-methylheptadecyl prop-2-enoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C=C STFXXRRQKFUYEU-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical group CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 2
- SDQROPCSKIYYAV-UHFFFAOYSA-N 2-methyloctane-1,8-diol Chemical compound OCC(C)CCCCCCO SDQROPCSKIYYAV-UHFFFAOYSA-N 0.000 description 2
- VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 description 2
- MWDGNKGKLOBESZ-UHFFFAOYSA-N 2-oxooctanal Chemical compound CCCCCCC(=O)C=O MWDGNKGKLOBESZ-UHFFFAOYSA-N 0.000 description 2
- KMSYDDGPKBBSNA-UHFFFAOYSA-N 3-ethyl-1-phenylpentan-1-one Chemical compound CCC(CC)CC(=O)C1=CC=CC=C1 KMSYDDGPKBBSNA-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 2
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 2
- PGDIJTMOHORACQ-UHFFFAOYSA-N 9-prop-2-enoyloxynonyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCOC(=O)C=C PGDIJTMOHORACQ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 230000001771 impaired effect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical compound IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical group CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000004980 phosphorus peroxides Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000001175 rotational moulding Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000012945 sealing adhesive Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/12—Esters of monohydric alcohols or phenols
- C08F120/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F120/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/046—Polymers of unsaturated carboxylic acids or derivatives thereof
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
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- C08F8/00—Chemical modification by after-treatment
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- C08F8/26—Removing halogen atoms or halogen-containing groups from the molecule
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- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
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- Polymerisation Methods In General (AREA)
Description
−OC(O)C(Ra)=CH2 (1)
(式中、Raは水素原子又は炭素数1〜20の有機基を示す)で表わされる(メタ)アクリロイル系基を、分子末端に1分子あたり少なくとも1個以上有するビニル系重合体、
(B)一般式(2):
Rb−(OC(O)C(Ra)=CH2)n (2)
(式中、Raは水素原子又は炭素数1〜20の有機基、Rbは炭素数6〜20の有機基、nは2〜6の整数を示す)で表わされる(メタ)アクリロイル系基を有するビニル系単量体、及び、
(C)開始剤、
を含有する電気、電子部品材料用組成物であって、
(A)成分と(B)成分の合計100重量%に対して、(B)成分を25重量%以上、45重量%以下含有することを特徴とする電子部品材料用組成物に関する。
−OC(O)C(Ra)=CH2 (1)
(式中、Raは水素原子又は炭素数1〜20の有機基を示す)で表わされる(メタ)アクリロイル系基を、分子末端に1分子あたり少なくとも1個以上有するビニル系重合体、
(B)一般式(2):
Rb−(OC(O)C(Ra)=CH2)n (2)
(式中、Raは水素原子又は炭素数1〜20の有機基、Rbは炭素数6〜20の有機基、nは2〜6の整数を示す)で表わされる(メタ)アクリロイル系基を有するビニル系単量体、
(D)一般式(3):
RC−OC(O)C(Ra)=CH2 (3)
(式中、Raは水素原子又は炭素数1〜20の有機基、RCは炭素数6〜20の有機基を示す)で表わされる(メタ)アクリロイル系基を有するビニル系単量体、及び
(C)開始剤、
を含有する電気、電子部品材料用組成物であって、
(A)成分と(B)成分と(D)成分の合計100重量%に対して、(B)成分と(D)成分の合計が25重量%以上、65重量%以下、かつ(B)成分が5重量%以上含有する電気、電子部品材料用組成物に関する。
<<(A)成分>>
本発明の(A)成分とは、
一般式(1):
−OC(O)C(Ra)=CH2 (1)
(式中、Raは水素原子又は炭素数1〜20の有機基を表わす)で表わされる(メタ)アクリロイル系基を、分子末端に1分子あたり少なくとも1個以上有するビニル系重合体である。
炭素数6〜20のアリール基としては、例えばフェニル基、ナフチル基等が挙げられる。
炭素数7〜20のアラルキル基としては、例えばベンジル基、フェニルエチル基等が挙げられる。
本発明で使用するビニル系重合体(A)は、種々の重合法により得ることができ、特に限定されないが、モノマーの汎用性、制御の容易性等の点からラジカル重合法が好ましく、ラジカル重合の中でも制御ラジカル重合がより好ましい。この制御ラジカル重合法は「連鎖移動剤法」と「リビングラジカル重合法」とに分類することができる。得られるビニル系重合体(A)の分子量、分子量分布の制御が容易であるリビングラジカル重合がさらに好ましく、原料の入手性、重合体末端への官能基導入の容易さから原子移動ラジカル重合が特に好ましい。上記ラジカル重合、制御ラジカル重合、連鎖移動剤法、リビングラジカル重合法、原子移動ラジカル重合は公知の重合法ではあるが、これら各重合法については、たとえば、特開2005−232419公報や、特開2006−291073公報などの記載を参照できる。
重合性の炭素−炭素二重結合導入は、公知の方法を利用することができる。例えば、特開2004−203932公報段落[0080]〜[0091]記載の方法が挙げられる。これらの方法の中でも制御がより容易である点から、ビニル系重合体の末端ハロゲン基を、重合性の炭素−炭素二重結合を有する化合物で置換することにより製造されたものであることが好ましい。
M+-OC(O)C(R)=CH2(4)
上記式(4)中のRの具体例としては、例えば、−H、−CH3、−CH2CH3、−(CH2)nCH3(nは2〜19の整数を表す)、−C6H5、−CH2OH、−CN、等が挙げられ、好ましくは−H、−CH3である。
<<(B)成分>>
本発明の(B)成分は、
一般式(2):
Rb−(OC(O)C(Ra)=CH2)n (2)
(式中、Raは水素原子又は炭素数1〜20の有機基、Rbは炭素数6〜20の有機基、nは2〜6の整数示す)で表わされる(メタ)アクリロイル系基を有するビニル系単量体であり、(A)成分と(B)成分の混合物中に25重量%以上、45重量%以下含まれる。一般式(2)のnは、硬化物の機械物性(伸び、強度)が優れる点で、3以下が好ましく、より好ましくは2である。
Raは、前述した一般式(1)のRaを同様に使用できる。
CH2=CHC(O)O−(CH2)n−OC(O)CH=CH2
(nは6〜20の整数)
CH2=C(CH3)C(O)O−(CH2)n−OC(O)C(CH3)=CH2
(nは6〜20の整数)
CH2=CHC(O)O−(CH2CH2O)n−OC(O)CH=CH2
(nは3〜10の整数)
CH2=C(CH3)C(O)O−(CH2CH2O)n−OC(O)C(CH3)=CH2
(nは3〜10の整数)
鎖状脂肪族構造を有する(B)成分としては、耐熱性および絶縁性が良い点で、エーテル構造を有さないビニル系単量体が好ましい。エーテル構造を有さないビニル系単量体としては、3―メチル―1,5―ペンタンジオールジ(メタ)アクリレート、1,6―ヘキサンジオールジ(メタ)アクリレート、1,7―へプタンジオールジ(メタ)アクリレート、1,8―オクタンジオールジ(メタ)アクリレート、2―メチル―1,8―オクタンジオールジ(メタ)アクリレート、1,9―ノナンジオールジ(メタ)アクリレート、1,10―デカンジオールジ(メタ)アクリレートなどが挙げられる。
(B)成分は、2種類以上を併用しても良い。
本発明の(D)成分は、
一般式(3):
Rc−OC(O)C(Ra)=CH2 (3)
(式中、Raは水素原子又は炭素数1〜20の有機基、Rcは炭素数6〜20の有機基を示す)で表わされる(メタ)アクリロイル系基を有するビニル系単量体であり、(A)成分と(B)成分と(D)成分の合計100重量%に対して、(B)成分と(D)成分の合計が25重量%以上、65重量%以下、かつ(B)成分が5重量%以上の範囲で含まれる。Raは、前述した一般式(1)のRaを同様に使用できる。
CH2=CHC(O)O−(CH2)n−CH3
(nは5〜19の整数)
CH2=C(CH3)C(O)O−(CH2)n−CH3
(nは5〜19の整数)
CH2=CHC(O)O−(CH2CH2O)n−CH3
(nは3〜9の整数)
CH2=C(CH3)C(O)O−(CH2CH2O)n−CH3
(nは3〜9の整数)
CH2=CHC(O)O−(CH2CH2O)n−CH2CH3
(nは2〜9の整数)
CH2=C(CH3)C(O)O−(CH2CH2O)n−CH2CH3
(nは2〜9の整数)
(D)成分としては、硬化物の機械物性(伸び、強度)が良くなり、しかも電気絶縁性、耐電極変色、低粘度化の効果が得られる点で、(B)成分と併用することが好ましい。
<<(C)成分>>
本発明の(C)成分の例としては、光重合開始剤、熱重合開始剤、レッドクス開始剤等が挙げられる。
熱重合開始剤は、単独で用いても、2種以上を併用してもよい。
レドックス系開始剤は、単独で用いても、2種以上を併用してもよい。
本発明の硬化性組成物は(A)成分のビニル系重合体、(B)成分のビニル系単量体、(C)成分の開始剤を含有し、必要により(D)成分のビニル系単量体を含有してなるが、物性を調整するために、さらに各種の添加剤、例えば、重合性のモノマー及び/またはオリゴマー、硬化調整剤、金属石鹸、充填材、微小中空粒子、可塑剤、接着性付与剤、溶剤、難燃剤、酸化防止剤、光安定剤、紫外線吸収剤、物性調整剤、ラジカル禁止剤、金属不活性化剤、オゾン劣化防止剤、リン系過酸化物分解剤、滑剤、顔料、発泡剤、光硬化性樹脂等を、必要に応じて適宜配合してもよい。これらの各種添加剤は、単独で用いてもよく、2種類以上を併用してもよい。
本発明の硬化性組成物は、本発明の効果を損なわない範囲で(B)成分、(D)成分以外の、モノマー及び/またはオリゴマーを添加することができる。ラジカル重合性の基を有する、モノマー及び/又はオリゴマーが、硬化性の点から好ましい。
ビニル系重合体へのエポキシ基導入は、公知の方法を利用することができる。例えば、特開2000−154212公報段落[0039]〜[0056]記載の方法が挙げられる。好ましい例も同段落中に記載されている。
得られたビニル系重合体へのヒドロシリル化反応可能なアルケニル基の導入方法としては、公知の方法を利用することができる。例えば、特開2004−059783公報段落[0042]〜[0086]記載の方法が挙げられる。さらに、好ましい例も同段落中に記載されている。
得られたビニル系重合体への加水分解性シリル基の導入方法としては、公知の方法を利用することができる。例えば、特開2000−191912公報段落[0076]〜[0138]記載の方法が挙げられる。さらに、好ましい例も同段落中に記載されている。
本発明の硬化性組成物には、各種酸化防止剤を必要に応じて用いてもよい。これらの酸化防止剤としては、アミン系酸化防止剤、ヒンダードフェノール系酸化防止剤、リン系酸化防止剤、イオウ系酸化防止剤等が挙げられる。
具体的には、2,6−ジ−tert−ブチル−4−メチルフェノール、2,6−ジ−tert−ブチル−4−エチルフェノール、モノ(またはジあるいはトリ)(αメチルベンジル)フェノール、2,2'−メチレンビス(4エチル−6−tert−ブチルフェノール)、2,2'−メチレンビス(4メチル−6−tert−ブチルフェノール)、4,4'−ブチリデンビス(3−メチル−6−tert−ブチルフェノール)、4,4'−チオビス(3−メチル−6−tert−ブチルフェノール)、2,5−ジ−tert−ブチルハイドロキノン、2,5−ジ−tert−アミルハイドロキノン、トリエチレングリコール−ビス−[3−(3−t−ブチル−5−メチル−4ヒドロキシフェニル)プロピオネート]、1,6−ヘキサンジオール−ビス[3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、2,4−ビス−(n−オクチルチオ)−6−(4−ヒドロキシ−3,5−ジ−t−ブチルアニリノ)−1,3,5−トリアジン、ペンタエリスリチル−テトラキス[3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、2,2−チオ−ジエチレンビス[3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、オクタデシル−3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート、N,N'−ヘキサメチレンビス(3,5−ジ−t−ブチル−4−ヒドロキシ−ヒドロシンナマミド)、3,5−ジ−t−ブチル−4−ヒドロキシ−ベンジルフォスフォネート−ジエチルエステル、1,3,5−トリメチル−2,4,6−トリス(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)ベンゼン、ビス(3,5−ジ−t−ブチル−4−ヒドロキシベンジルホスホン酸エチル)カルシウム、トリス−(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)イソシアヌレート、2,4−2,4−ビス[(オクチルチオ)メチル]o−クレゾール、N,N'−ビス[3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオニル]ヒドラジン、トリス(2,4−ジ−t−ブチルフェニル)フォスファイト、2−(5−メチル−2−ヒドロキシフェニル)ベンゾトリアゾール、2−[2−ヒドロキシ−3,5−ビス(α,α−ジメチルベンジル)フェニル]−2H−ベンゾトリアゾール、2−(3,5−ジ−t−ブチル−2−ヒドロキシフェニル)ベンゾトリアゾール、2−(3−t−ブチル−5−メチル−2−ヒドロキシフェニル)−5−クロロベンゾトリアゾール、2−(3,5−ジ−t−ブチル−2−ヒドロキシフェニル)−5−クロロベンゾトリアゾール、2−(3,5−ジ−t−アミル−2−ヒドロキシフェニル)ベンゾトリアゾール、2−(2'−ヒドロキシ−5'−t−オクチルフェニル)−ベンゾトリアゾール、メチル−3−[3−t−ブチル−5−(2H−ベンゾトリアゾール−2−イル)−4−ヒドロキシフェニル]プロピオネート−ポリエチレングリコール(分子量約300)との縮合物、ヒドロキシフェニルベンゾトリアゾール誘導体、2−(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)−2−n−ブチルマロン酸ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)、2,4−ジ−t−ブチルフェニル−3,5−ジ−t−ブチル−4−ヒドロキシベンゾエート等が挙げられる。
本発明の硬化性組成物は、全ての配合成分を予め配合密封した1液型として調製でき、また、開始剤や硬化触媒や架橋剤だけを抜いたA液と、開始剤や硬化触媒や架橋剤を充填材、可塑剤、溶剤等と混合したB液を成形直前に混合する2液型としても調製できる。
本発明の硬化物は、上記硬化性組成物を硬化させて得られるものである。
当該硬化性組成物を硬化させる方法としては、特に限定されない。
その他の開始剤としてレドックス系開始剤を用いる場合、硬化温度は、−50℃〜250℃が好ましく、0℃〜180℃がより好ましい。
本発明の硬化性組成物を成形体として用いる場合の成形方法としては、特に限定されず、一般に使用されている各種の成形方法を用いることができる。例えば、注型成形、圧縮成形、トランフファー成形、射出成形、押し出し成形、回転成形、中空成形、熱成形等が挙げられる。特に自動化、連続化が可能で、生産性に優れるという点から、ロール成形、カレンダー成形、押出し成形、液状射出成形、射出成形によるものが好ましい。
本発明の硬化性組成物および硬化物は、電極金属に接する電気・電子部品材料に好適であるが、特に限定されず、電線・ケーブル用絶縁被覆材等の電気絶縁材、シール材、接着剤、粘着剤、コンフォーマルコーティング剤、電気電子用ポッティング剤、放熱材、防水材、防振・制振・免振材、フィルム、マリンデッキコーキング、注型材料、または、成形材料に用いられる。
(ただし、1H−NMRはBruker社製ASX−400を使用し、溶媒として重クロロホルムを用いて23℃にて測定した。)
得られたポリマーおよび配合部の粘度は、JIS K 7117−2円すい−平板システムに準拠し、東機産業製E型粘度計を使用し、測定温度23℃で測定した。
通電高温高湿試験後、櫛型基板を目視で観察した。櫛型基板には陽極、陰極、電荷をかけない電極があり、これら電極金属間の変色差がないものを○、電極金属間の変色差があるものを×とした。
JIS K 6251に準じて、硬化物を2mm厚さ、3号ダンベルのサイズに切り出し、引張り速度200mm/分、23℃×55%RH条件下で測定した。引張り試験には、島津製オートグラフ、AG−2000Aを使用した。
JIS K 3197の8.5.4項の電圧印加耐湿性試験に準じて、櫛型基板を用いて試験した。櫛型基板の導体は銅、基材はガラスエポキシ(FR4)、導体幅は0.318mm、導体間隔は0.318mm、重ね代は15.75mmとした。櫛型基板に50μm厚さの塗膜を作製した後、導線をハンダ付けした。導線は高温高湿条件で使用できる被覆導線(フッソ樹脂被覆電線、1.2mmΦ、定格600V)を使用した。
恒温恒湿機内に櫛型基板を設置し、導線を恒温恒湿機外へ延ばして常時通電した。所定時間後、櫛型基板は高温高湿のままで、恒温恒湿機外へ延ばした導線末端で絶縁値を測定した。通電高温高湿試験条件はDC50V、85℃85%RH、500時間とした。
フュージョンUVシステムズ・ジャパン株式会社製、型式 LH6、Hバルブを使用した。紫外線硬化条件は1500mW/cm2、3000mJ/cm2とした。
アクリル酸n−ブチル100部を脱酸素した。反応容器の内部を脱酸素し、臭化第一銅0.17部、アクリル酸n−ブチルのうち20部、アセトニトリル4.4部、2,5−ジブロモアジピン酸ジエチル3.5部を添加して70℃で混合し、ペンタメチルジエチレントリアミン(以下、トリアミンと略す)0.010部を添加し、重合反応を開始した。モノマー混合物80部を逐次添加し、重合反応を進めた。重合途中、適宜トリアミンを追加して重合速度を調整し、内温を約80℃〜約90℃に調整しながら重合を進行させた。モノマー転化率(重合反応率)が約95%以上の時点で反応容器気相部に酸素‐窒素混合ガスを導入し、内温を約80℃〜約90℃に保ちながら加熱攪拌した。揮発分を減圧除去して濃縮した。これを酢酸ブチルで希釈し、ろ過助剤を加えてろ過した。ろ液に対して吸着剤(協和化学工業製キョーワード700SEN、キョーワード500SH)を添加して加熱撹拌後、濾過してろ液を濃縮した。これをN,N−ジメチルアセトアミドに溶解させ、アクリル酸カリウム(末端Br基に対して約2モル当量)、熱安定剤(H−TEMPO:4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−n−オキシル)、吸着剤(キョーワード700SEN)、を添加し、約70℃で加熱攪拌した。揮発分を減圧留去してから酢酸ブチルで希釈し、ろ過助剤を添加してろ過した。ろ液を濃縮し、両末端にアクリロイル基を有する「重合体II」を得た。
「重合体I」の数平均分子量は12,000、分子量分布は1.2、重合体1分子当たりに導入された平均のアクリロイル基数は1.8であった。
アクリル酸n−ブチル2部およびアクリル酸2−エチルヘキシル98部からなるモノマー混合物を脱酸素した。反応容器の内部を脱酸素し、臭化第一銅0.29部、モノマー混合物のうち20部、アセトニトリル8.9部、2,5−ジブロモアジピン酸ジエチル2.5部を添加して80℃で混合し、ペンタメチルジエチレントリアミン(以下、トリアミンと略す)0.014部を添加し、重合反応を開始した。モノマー混合物80部を逐次添加し、重合反応を進めた。重合途中、適宜トリアミンを追加して重合速度を調整し、内温を約80℃〜約90℃に調整しながら重合を進行させた。モノマー転化率(重合反応率)が約95%以上の時点で反応容器気相部に酸素‐窒素混合ガスを導入し、内温を約80℃〜約90℃に保ちながら加熱攪拌した。揮発分を減圧除去して濃縮した。これを酢酸ブチルで希釈し、ろ過助剤を加えてろ過した。ろ液に対して吸着剤(協和化学工業製キョーワード700SEN、キョーワード500SH)を添加して加熱撹拌後、濾過してろ液を濃縮した。これをN,N−ジメチルアセトアミドに溶解させ、アクリル酸カリウム(末端Br基に対して約2モル当量)、熱安定剤(H−TEMPO:4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−n−オキシル)、吸着剤(キョーワード700SEN)、を添加し、約70℃で加熱攪拌した。揮発分を減圧留去してから酢酸ブチルで希釈し、ろ過助剤を添加してろ過した。ろ液を濃縮し、両末端にアクリロイル基を有する「重合体II」を得た。
「重合体II」の数平均分子量は13500、分子量分布は1.3、重合体1分子当たりに導入された
平均のアクリロイル基数は1.6であった。
配合方法を説明する。製造例1または2で得た(A)成分の「重合体I」または「重合体II」
に酸化防止剤を添加し、120℃で2時間加熱混合して、酸化防止剤を「重合体I」または「重合体II」に溶かした。50℃以下に冷却してから、(B)成分、(D)成分、(C)成分、その他成分を
添加し、攪拌脱泡装置((株)シンキー製、ARE−250)で均一にした。なお(C)成分は、DAROCUR1173(チバ・ジャパン製)と、IRGACURE819(チバ・ジャパン製)を予め加熱溶解したものを使用した。配合量(「重量部」)を表1〜3に示す。なお表中、(B)成分のライトアクリレートDCP−Aはジメチロール−トリシクロデカンジアクリレート、V#260は1,9−ノナンジオールジアクリレート、(D)成分のISTAはイソステアリルアクリレート、IBXAはイソボルニルアクリレート、FA−513Aはジシクロペンタニルアクリレート、酸化防止剤のナウガード445は4,4'−ビス(α,α'―ジメチルベンジル)ジフェニルアミン、IRGANOX1010はテトラキス−[メチレン−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]メタンを示す。
Claims (12)
- (A)一般式(1):
−OC(O)C(Ra)=CH2 (1)
(式中、Raは水素原子又は炭素数1〜20の有機基を示す)で表わされる(メタ)アクリロイル系基を、分子末端に1分子あたり少なくとも1個以上有するビニル系重合体、
(B)一般式(2):
Rb−(OC(O)C(Ra)=CH2)n (2)
(式中、Raは水素原子又は炭素数1〜20の有機基、Rbは炭素数6〜20の有機基、nは2〜6の整数を示す)で表わされる(メタ)アクリロイル系基を有するビニル系単量体、及び、
(C)開始剤、
を含有する電気、電子部品材料用組成物であって、
(A)成分と(B)成分の合計100重量%に対して、(B)成分を25重量%以上、45重量%以下含有することを特徴とする電子部品材料用組成物。 - (A)一般式(1):
−OC(O)C(Ra)=CH2 (1)
(式中、Raは水素原子又は炭素数1〜20の有機基を示す)で表わされる(メタ)アクリロイル系基を、分子末端に1分子あたり少なくとも1個以上有するビニル系重合体、
(B)一般式(2):
Rb−(OC(O)C(Ra)=CH2)n (2)
(式中、Raは水素原子又は炭素数1〜20の有機基、Rbは炭素数6〜20の有機基、nは2〜6の整数を示す)で表わされる(メタ)アクリロイル系基を有するビニル系単量体、
(D)一般式(3):
RC−OC(O)C(Ra)=CH2 (3)
(式中、Raは水素原子又は炭素数1〜20の有機基、RCは炭素数6〜20の有機基を示す)で表わされる(メタ)アクリロイル系基を有するビニル系単量体、及び
(C)開始剤、
を含有する電気、電子部品材料用組成物であって、
(A)成分と(B)成分と(D)成分の合計100重量%に対して、(B)成分と(D)成分の合計が25重量%以上、65重量%以下、かつ(B)成分が5重量%以上含有する電気、電子部品材料用組成物。 - (A)成分と(B)成分と(D)成分の合計100重量%に対して、(B)成分と(D)成分の合計が30重量%以上、55重量%以下、かつ(B)成分が15重量%以上含有する請求項2に記載の電気、電子部品材料用組成物。
- (C)成分の量が、(A)成分、(B)成分、(D)成分の合計100重量部に対して、0.001〜10重量部であることを特徴とする請求項1〜3のいずれかに記載の電気、電子部品材料用組成物。
- (A)成分の主鎖が、アクリル酸エステル系単量体を重合して製造される請求項1〜4のいずれかに記載の電気、電子部品材料用組成物。
- (A)成分の数平均分子量が、3000以上である請求項1〜5のいずれかに記載の電気、電子部品材料用組成物。
- (A)成分のビニル系重合体が、ゲルパーミエーションクロマトグラフィーで測定した重量平均分子量と数平均分子量の比の値が1.8未満である請求項1〜6のいずれかに記載の電気、電子部品材料用組成物。
- (B)成分が、(メタ)アクリロイル系基を一分子中に2個有するビニル系単量体である請求項1〜7のいずれかに記載の電気、電子部品材料用組成物。
- (C)成分が光ラジカル開始剤である請求項1〜8のいずれかに記載の電気、電子部品材料用組成物。
- 請求項1〜9のいずれかに記載の電気、電子部品材料用組成物が電極金属に接する電気、電子部品材料用組成物。
- 請求項1〜10のいずれかに記載の電気、電子部品材料用組成物を硬化して得られる電気、電子部品材料。
- 請求項1〜11のいずれかに記載の電気、電子部品材料用組成物を、活性エネルギー線または熱により硬化して得られる硬化物。
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