JP2016176009A - Curable composition - Google Patents
Curable composition Download PDFInfo
- Publication number
- JP2016176009A JP2016176009A JP2015057690A JP2015057690A JP2016176009A JP 2016176009 A JP2016176009 A JP 2016176009A JP 2015057690 A JP2015057690 A JP 2015057690A JP 2015057690 A JP2015057690 A JP 2015057690A JP 2016176009 A JP2016176009 A JP 2016176009A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- meth
- compound
- curable composition
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 83
- -1 allylsilane compound Chemical class 0.000 claims abstract description 210
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 22
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000003086 colorant Substances 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000000049 pigment Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000007870 radical polymerization initiator Substances 0.000 claims description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 238000012360 testing method Methods 0.000 abstract description 17
- 238000003860 storage Methods 0.000 abstract description 12
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 88
- 239000002253 acid Substances 0.000 description 45
- 239000004593 Epoxy Substances 0.000 description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 150000007519 polyprotic acids Polymers 0.000 description 19
- 150000008065 acid anhydrides Chemical class 0.000 description 17
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000003999 initiator Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 150000008064 anhydrides Chemical class 0.000 description 13
- 239000000975 dye Substances 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000006229 carbon black Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 10
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 10
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 10
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 229940049920 malate Drugs 0.000 description 9
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 229920002120 photoresistant polymer Polymers 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 6
- 150000002484 inorganic compounds Chemical class 0.000 description 6
- 229910010272 inorganic material Inorganic materials 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 5
- 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 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 4
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000005530 etching Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 3
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- NPKKFQUHBHQTSH-UHFFFAOYSA-N 2-(decoxymethyl)oxirane Chemical compound CCCCCCCCCCOCC1CO1 NPKKFQUHBHQTSH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 3
- DGQOZCNCJKEVOA-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1CC(=O)OC1=O DGQOZCNCJKEVOA-UHFFFAOYSA-N 0.000 description 3
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-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
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- 239000013638 trimer Substances 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 229910052720 vanadium Inorganic materials 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
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Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Epoxy Resins (AREA)
Abstract
Description
本発明は、アリルシラン化合物を含有する硬化性組成物に関する。 The present invention relates to a curable composition containing an allylsilane compound.
重合性化合物及び重合開始剤を含有する硬化性組成物は、必要に応じて着色剤が含まれていてもよいが、紫外線等の活性エネルギー線の照射、又は加熱することによって重合硬化させることができるので、ディスプレイ材料等の様々な用途において有用である。 The curable composition containing a polymerizable compound and a polymerization initiator may contain a colorant as necessary, but may be polymerized and cured by irradiation with active energy rays such as ultraviolet rays or heating. This is useful in various applications such as display materials.
最近、電子材料に用いられる硬化性組成物の長期信頼性試験として、耐湿熱試験後の密着強度試験が実施されている。耐湿熱試験による密着強度の劣化を防止する方法として硬化性組成物にアルコキシシラン化合物を添加する手法が用いられるが、アルコキシ部位の加水分解とそれによる重合反応に起因する硬化性組成物の増粘等が起こり保存安定性に問題がある。 Recently, as a long-term reliability test of a curable composition used for an electronic material, an adhesion strength test after a wet heat resistance test has been performed. A method of adding an alkoxysilane compound to a curable composition is used as a method to prevent deterioration of adhesion strength due to a moist heat resistance test, but the viscosity of the curable composition is increased due to hydrolysis of the alkoxy site and resulting polymerization reaction. Etc. occur and there is a problem in storage stability.
下記特許文献1、2及び3には、それぞれアルコキシシラン化合物及びアルコキシシラン化合物を構成要素とする重合体を含有する組成物が開示されている。下記特許文献1には、塗装作業性に優れ、加熱による着色や減量のない耐熱性に優れる熱硬化性樹脂組成物が開示され、下記特許文献2には、耐熱性、酸素バリア性、透湿性、耐候性及び可とう性に優れる光硬化性を有した組成物が開示され、下記特許文献3には、現像マージンが大きく、基材への密着性と絶縁性を有す特徴とする感放射線樹脂組成物が開示されている。何れの特許文献においても組成物の保存安定性が悪いという課題がある。 The following Patent Documents 1, 2 and 3 disclose compositions containing an alkoxysilane compound and a polymer having an alkoxysilane compound as a constituent element, respectively. The following Patent Document 1 discloses a thermosetting resin composition having excellent coating workability and excellent heat resistance without coloring or weight loss by heating, and Patent Document 2 described below discloses heat resistance, oxygen barrier properties, and moisture permeability. A radiation-sensitive composition having excellent weather resistance and flexibility is disclosed, and the following Patent Document 3 has a large development margin and is characterized by having adhesion to a substrate and insulation. A resin composition is disclosed. In any patent document, there is a problem that the storage stability of the composition is poor.
上述の如く、従来の硬化性組成物において耐湿熱試験後の密着強度と保存安定性の両立を図ることが困難であるという課題がある。
従って、本願発明の目的は、耐湿熱試験後の密着強度と保存安定性が両立された硬化性組成物を提供することにある。
As described above, the conventional curable composition has a problem that it is difficult to achieve both the adhesion strength after the wet heat resistance test and the storage stability.
Accordingly, an object of the present invention is to provide a curable composition having both adhesion strength after a heat and humidity resistance test and storage stability.
本発明者等は、鋭意検討を重ねた結果、下記一般式(I)で表されるアリルシラン化合
物(A)、重合性化合物(B)及び重合開始剤(C)を含有する硬化性組成物が、耐湿熱試験後の密着強度と保存安定性の向上に好適であることを知見し、本発明に到達した。
また、本発明は、更に着色剤を添加した硬化性組成物、また、硬化性組成物を硬化させる方法、また、硬化性組成物を用いて得られる硬化物を提供するものである。 Moreover, this invention provides the curable composition which added the coloring agent further, the method of hardening a curable composition, and the hardened | cured material obtained using a curable composition.
本発明によれば、保存安定性と耐湿熱試験後の密着強度の両立を可能とする硬化性組成物を提供できる。 ADVANTAGE OF THE INVENTION According to this invention, the curable composition which enables coexistence of storage stability and the adhesive strength after a heat-and-moisture resistance test can be provided.
以下、本発明の硬化性組成物について、好ましい実施形態に基づき説明する。 Hereinafter, the curable composition of this invention is demonstrated based on preferable embodiment.
本発明の硬化性組成物は上記一般式(I)で表されるアリルシラン化合物(A)(以下
、単にアリルシラン化合物(A)ともいう)、重合性化合物(B)及び重合開始剤(C)を含有する。以下、各成分について順に説明する。
The curable composition of the present invention comprises an allylsilane compound (A) represented by the above general formula (I) (hereinafter also simply referred to as an allylsilane compound (A)), a polymerizable compound (B) and a polymerization initiator (C). contains. Hereinafter, each component will be described in order.
<アリルシラン化合物(A)>
本発明の硬化性組成物に用いられるアリルシラン化合物(A)は、上記一般式(I)で
表わされる構造を有する。
<Allylsilane compound (A)>
The allylsilane compound (A) used in the curable composition of the present invention has a structure represented by the above general formula (I).
上記一般式(I)中、R1で表される炭素数1〜20のアルキル基としては、例えば、
メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、t−ブチル、n−ペンチル、イソペンチル、t−ペンチル、ネオペンチル、ヘキシル、イソヘキシル、n−ヘプチル、t−ヘプチル、n−オクチル、イソオクチル、t−オクチル、2−エチルヘキシル、ノニル、デシル、ウンデシル、ドデシル、トリデシル、イソトリデシル、ミリスチル、パルミチル及びステアリル等が挙げられ、
炭素数1〜20のアルキル基の置換基としては、例えば(メタ)アクリロイル基、ビニル基、アリル基、エポキシ基、アミノ基、イソシアネート基、カルボキシル基、ヒドロキシ基、アリール基、複素環基、脂環式炭化水素基、ハロゲン原子及び−MgX基(ここで、Xはハロゲン原子、好ましくは臭素原子又は塩素原子)が挙げられ、密着強度が良いことからエポキシ基及びイソシアネート基が特に好ましい。但し置換基の炭素数は上記アルキル基の炭素数として含まない。
R1で表される炭素原子数1〜10のアルコキシ基としては、メチルオキシ、エチルオキシ、イソプロピルオキシ、プロピルオキシ、ブチルオキシ、ペンチルオキシ、イソペンチルオキシ、ヘキシルオキシ、ヘプチルオキシ、オクチルオキシ及び2−エチルヘキシルオキシ等が挙げられる。
R1で表される炭素原子数6〜20のアリール基としては、フェニル、ナフチル、アントラセン−1−イル、フェナントレン−1−イル、o−トリル、m−トリル、p−トリル、4−ビニルフェニル、3−イソプロピルフェニル、4−イソプロピルフェニル、4−ブチルフェニル、4−イソブチルフェニル、4−t−ブチルフェニル、4−ヘキシルフェニル、4−シクロヘキシルフェニル、4−オクチルフェニル、4−(2−エチルヘキシル)フェニル、2,3−ジメチルフェニル、2,4−ジメチルフェニル、2,5−ジメチルフェニル、2,6−ジメチルフェニル、3,4−ジメチルフェニル、3,5−ジメチルフェニル、2,4−ジ−t−ブチルフェニル、2,5−ジ−t−ブチルフェニル、2,6−ジ−t−ブチルフェニル、2,4−ジ−t−ペンチルフェニル、2,5−ジ−t−アミルフェニル、シクロヘキシルフェニル、ビフェニル、2,4,5−トリメチルフェニル、4−クロロフェニル、3,4−ジクロロフェニル、4−トリクロロフェニル、4−トリフルオロフェニル及びパーフルオロフェニル等が挙げられる。
R1で表されるハロゲン原子としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられる。
In the general formula (I), the alkyl group having 1 to 20 carbon atoms represented by R 1, for example,
Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, n-pentyl, isopentyl, t-pentyl, neopentyl, hexyl, isohexyl, n-heptyl, t-heptyl, n-octyl, isooctyl, t-octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, isotridecyl, myristyl, palmityl, stearyl, etc.
Examples of the substituent of the alkyl group having 1 to 20 carbon atoms include (meth) acryloyl group, vinyl group, allyl group, epoxy group, amino group, isocyanate group, carboxyl group, hydroxy group, aryl group, heterocyclic group, and fat. Examples thereof include a cyclic hydrocarbon group, a halogen atom, and a —MgX group (where X is a halogen atom, preferably a bromine atom or a chlorine atom), and an epoxy group and an isocyanate group are particularly preferable because of good adhesion strength. However, the carbon number of the substituent is not included as the carbon number of the alkyl group.
Examples of the alkoxy group having 1 to 10 carbon atoms represented by R 1 include methyloxy, ethyloxy, isopropyloxy, propyloxy, butyloxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy and 2-ethylhexyl. Examples include oxy.
Examples of the aryl group having 6 to 20 carbon atoms represented by R 1 include phenyl, naphthyl, anthracen-1-yl, phenanthren-1-yl, o-tolyl, m-tolyl, p-tolyl, and 4-vinylphenyl. 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-t-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) Phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di- t-butylphenyl, 2,5-di-t-butylphenyl, 2,6-di-t-butylphenyl, 2,4 Di-t-pentylphenyl, 2,5-di-t-amylphenyl, cyclohexylphenyl, biphenyl, 2,4,5-trimethylphenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 4-trichlorophenyl, 4-triphenyl Examples include fluorophenyl and perfluorophenyl.
Examples of the halogen atom represented by R 1 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
上記アリルシラン化合物(A)としては、具体的には、アリルビニルシラン、ジアリルジビニルシラン、アリルジメチルシラン、アリルトリメチルシラン、トリアリルメチルシラン、クロロジメチルアリルシラン、ジクロロメチルシラン、クロロメチルジアリルシラン、アリルブロモジメチルシラン、アリルブロモメチルジメチルシラン、ジアリルジエトキシシラン、トリアリル−3−ブロモプロピルシラン、トリアリル−4−メトキシフェニルシラン、テトラアリルシラン及び下記化合物No.A1〜12等が挙げられる。
上記アリルシラン化合物(A)としては、市販品を用いることもでき、例えば、SiA−103、SiA−203、SiA−303、SiA−403、SiA−503、SiA−603、SiA−703、SiA−803及びSiA−903(共栄社化学製)等が挙げられる。
Specific examples of the allylsilane compound (A) include allylvinylsilane, diallyldivinylsilane, allyldimethylsilane, allyltrimethylsilane, triallylmethylsilane, chlorodimethylallylsilane, dichloromethylsilane, chloromethyldiallylsilane, and allylbromodimethyl. Silane, allylbromomethyldimethylsilane, diallyldiethoxysilane, triallyl-3-bromopropylsilane, triallyl-4-methoxyphenylsilane, tetraallylsilane, and the following compound Nos. A1-12 etc. are mentioned.
A commercial item can also be used as said allylsilane compound (A), for example, SiA-103, SiA-203, SiA-303, SiA-403, SiA-503, SiA-603, SiA-703, SiA-803. And SiA-903 (manufactured by Kyoeisha Chemical Co., Ltd.).
上記アリルシラン化合物(A)の中では、耐湿熱試験後の密着強度が良好なことからbが2以上であるものが好ましく、より好ましくは、bが3、aが1でR1が炭素数1〜20のアルキル基であるもの、特に置換基としてエポキシ基又はイソシアネート基を有する基を少なくとも1つ以上含有するものが好ましい。 Among the allylsilane compounds (A), those having b of 2 or more are preferable because adhesion strength after the wet heat resistance test is good, and more preferably, b is 3, a is 1 and R 1 is 1 carbon. Those having an alkyl group of ˜20, particularly those containing at least one group having an epoxy group or an isocyanate group as a substituent are preferred.
本発明の硬化性組成物において、アリルシラン化合物(A)の含有量は、特に限定されるものではないが、アリルシラン化合物(A)、重合性化合物(B)及び重合開始剤(C)の合計100質量部に対して、基材への耐湿熱試験後の密着性が良好なことから好ましくは、0.1〜10質量部、より好ましくは、0.5〜5.0質量部である。アリルシラン化合物(A)の含有量が、0.1質量部より小さいと基材への密着性が劣り、10質量部より大きいと、硬化性が劣る。
例えば膜厚1〜3μmの硬化膜を形成する場合には、アリルシラン化合物(A)の含有量は、アリルシラン化合物(A)、重合性化合物(B)及び重合開始剤(C)の合計100質量部に対して、好ましくは0.1〜10質量部、より好ましくは、0.5〜5.0質量部である。
In the curable composition of the present invention, the content of the allylsilane compound (A) is not particularly limited, but a total of 100 of the allylsilane compound (A), the polymerizable compound (B), and the polymerization initiator (C). Preferably it is 0.1-10 mass parts, More preferably, it is 0.5-5.0 mass parts from the favorable adhesiveness after the moisture-and-heat test to a base material with respect to the mass part. When the content of the allylsilane compound (A) is less than 0.1 parts by mass, the adhesion to the substrate is inferior, and when it is greater than 10 parts by mass, the curability is inferior.
For example, when a cured film having a thickness of 1 to 3 μm is formed, the content of the allylsilane compound (A) is 100 parts by mass in total of the allylsilane compound (A), the polymerizable compound (B), and the polymerization initiator (C). The amount is preferably 0.1 to 10 parts by mass, and more preferably 0.5 to 5.0 parts by mass.
<重合性化合物(B)>
本発明の硬化性組成物に用いられる重合性化合物(B)は、ラジカル重合、カチオン重合及びアニオン重合等の重合性を有する化合物を選択することができるが、反応性が良く、重合性化合物の種類が多いことからラジカル重合性化合物及びカチオン重合性化合物を好ましく用いることができる。
<Polymerizable compound (B)>
As the polymerizable compound (B) used in the curable composition of the present invention, a compound having polymerizability such as radical polymerization, cationic polymerization, and anion polymerization can be selected. Since there are many types, radically polymerizable compounds and cationically polymerizable compounds can be preferably used.
・ラジカル重合性化合物について
ラジカル重合性化合物としては、特に限定されず、従来既知のラジカル重合性を持つ化合物を用いることができるが、例えば、エチレン、プロピレン、ブチレン、イソブチレン、塩化ビニル、塩化ビニリデン、フッ化ビニリデン及びテトラフルオロエチレン等の不飽和脂肪族炭化水素;(メタ)アクリル酸、α―クロルアクリル酸、イタコン酸、マレイン酸、シトラコン酸、フマル酸、ハイミック酸、クロトン酸、イソクロトン酸、ビニル酢酸、アリル酢酸、桂皮酸、ソルビン酸、メサコン酸、コハク酸モノ[2−(メタ)アクリロイロキシエチル]、フタル酸モノ[2−(メタ)アクリロイロキシエチル]及びω−カルボキシポリカプロラクトンモノ(メタ)アクリレート等の両末端にカルボキシ基と水酸基とを有するポリマーのモノ(メタ)アクリレート;ヒドロキシエチル(メタ)アクリレート・マレート、ヒドロキシプロピル(メタ)アクリレート・マレート、ジシクロペンタジエン・マレート及び1個のカルボキシル基と2個以上の(メタ)アクリロイル基とを有する多官能(メタ)アクリレート等の不飽和一塩基酸;(メタ)アクリル酸−2−ヒドロキシエチル、(メタ)アクリル酸−2−ヒドロキシプロピル、(メタ)アクリル酸グリシジル、下記化合物No.B1〜No.B4、(メタ)アクリル酸メチル、 (メタ)アクリル酸ブチル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸−t−ブチル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸n−オクチル、(メタ)アクリル酸イソオクチル、(メタ)アクリル酸イソノニル、(メタ)アクリル酸ステアリル、(メタ)アクリル酸ラウリル、(メタ)アクリル酸メトキシエチル、(メタ)アクリル酸ジメチルアミノメチル、(メタ)アクリル酸ジメチルアミノエチル、(メタ)アクリル酸アミノプロピル、(メタ)アクリル酸ジメチルアミノプロピル、(メタ)アクリル酸エトキシエチル、(メタ)アクリル酸ポリ(エトキシ)エチル、(メタ)アクリル酸ブトキシエトキシエチル、(メタ)アクリル酸エチルヘキシル、(メタ)アクリル酸フェノキシエチル、(メタ)アクリル酸テトラヒドロフリル、(メタ)アクリル酸ビニル、(メタ)アクリル酸アリル、(メタ)アクリル酸ベンジル、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、1,4−ブタンジオールジ(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、トリメチロールエタントリ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、トリシクロデカンジメチロールジ(メタ)アクリレート、トリ[(メタ)アクリロイルエチル]イソシアヌレート及びポリエステル(メタ)アクリレートオリゴマー等の不飽和一塩基酸及び多価アルコール又は多価フェノールのエステル;(メタ)アクリル酸亜鉛及び(メタ)アクリル酸マグネシウム等の不飽和多塩基酸の金属塩;マレイン酸無水物、イタコン酸無水物、シトラコン酸無水物、メチルテトラヒドロ無水フタル酸、テトラヒドロ無水フタル酸、トリアルキルテトラヒドロ無水フタル酸、5−(2,5−ジオキソテトラヒドロフリル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸無水物、トリアルキルテトラヒドロ無水フタル酸−無水マレイン酸付加物、ドデセニル無水コハク酸及び無水メチルハイミック酸等の不飽和多塩基酸の酸無水物;(メタ)アクリルアミド、メチレンビス−(メタ)アクリルアミド、ジエチレントリアミントリス(メタ)アクリルアミド、キシリレンビス(メタ)アクリルアミド、α−クロロアクリルアミド及びN−2−ヒドロキシエチル(メタ)アクリルアミド等の不飽和一塩基酸と多価アミンのアミド;アクロレイン等の不飽和アルデヒド;(メタ)アクリロニトリル、α−クロロアクリロニトリル、シアン化ビニリデン及びシアン化アリル等の不飽和ニトリル;スチレン、4−メチルスチレン、4−エチルスチレン、4−メトキシスチレン、4−ヒドロキシスチレン、4−クロロスチレン、ジビニルベンゼン、ビニルトルエン、ビニル安息香酸、ビニルフェノール、ビニルスルホン酸、4−ビニルベンゼンスルホン酸、ビニルベンジルメチルエーテル及びビニルベンジルグリシジルエーテル等の不飽和芳香族化合物;メチルビニルケトン等の不飽和ケトン;ビニルアミン、アリルアミン、N−ビニルピロリドン及びビニルピペリジン等の不飽和アミン化合物;アリルアルコール及びクロチルアルコール等のビニルアルコール;ビニルメチルエーテル、ビニルエチルエーテル、n−ブチルビニルエーテル、イソブチルビニルエーテル及びアリルグリシジルエーテル等のビニルエーテル;マレイミド、N−フェニルマレイミド及びN−シクロヘキシルマレイミド等の不飽和イミド類;インデン及び1−メチルインデン等のインデン類;1,3−ブタジエン、イソプレン及びクロロプレン等の脂肪族共役ジエン類;ポリスチレン、ポリメチル(メタ)アクリレート、ポリ−n−ブチル(メタ)アクリレート及びポリシロキサン等の重合体分子鎖の末端にモノ(メタ)アクリロイル基を有するマクロモノマー類;ビニルクロリド、ビニリデンクロリド、ジビニルスクシナート、ジアリルフタラート、トリアリルホスファート、トリアリルイソシアヌラート、ビニルチオエーテル、ビニルイミダゾール、ビニルオキサゾリン、ビニルカルバゾール、ビニルピロリドン、ビニルピリジン、水酸基含有ビニルモノマー、ポリイソシアネート化合物のビニルウレタン化合物、水酸基含有ビニルモノマー及びポリエポキシ化合物等のビニルエポキシ化合物が挙げられる。
上記ラジカル重合性化合物としては、市販品を用いることもでき、例えば、カヤラッドDPHA、DPEA−12、PEG400DA、THE−330、RP−1040、NPGDA、PET30(日本化薬社製)、アロニックスM−215、M−350(東亞合成社製)、NKエステルA−DPH、A−TMPT、A−DCP、A−HD−N、TMPT、DCP、NPG及びHD−N(新中村化学工業社製)等が挙げられる。
・Regarding the radically polymerizable compound, the radically polymerizable compound is not particularly limited, and a compound having a conventionally known radically polymerizable property can be used. For example, ethylene, propylene, butylene, isobutylene, vinyl chloride, vinylidene chloride, Unsaturated aliphatic hydrocarbons such as vinylidene fluoride and tetrafluoroethylene; (meth) acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinyl Acetic acid, allyl acetic acid, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl] and ω-carboxypolycaprolactone mono A carboxy group and a hydroxyl group at both ends of (meth) acrylate, etc. Mono (meth) acrylate of a polymer having: hydroxyethyl (meth) acrylate malate, hydroxypropyl (meth) acrylate malate, dicyclopentadiene malate and one carboxyl group and two or more (meth) acryloyl groups Unsaturated monobasic acids such as polyfunctional (meth) acrylates; (meth) acrylic acid-2-hydroxyethyl, (meth) acrylic acid-2-hydroxypropyl, glycidyl (meth) acrylate, the following compound No. B1-No. B4, methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (meth) acrylate, (meta ) Ethylhexyl acrylate, (meth) acrylic acid Phenoxyethyl, tetrahydrofuryl (meth) acrylate, vinyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol Di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, trimethylolethanetri (Meth) acrylate, trimethylolpropane tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, pentaerythritol Unsaturated monobasic acids such as tra (meth) acrylate, pentaerythritol tri (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate, tri [(meth) acryloylethyl] isocyanurate and polyester (meth) acrylate oligomers; Esters of polyhydric alcohols or polyphenols; metal salts of unsaturated polybasic acids such as zinc (meth) acrylate and magnesium (meth) acrylate; maleic anhydride, itaconic anhydride, citraconic anhydride, methyl Tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydro Phthalic anhydride Hydrous maleic acid adduct, acid anhydrides of unsaturated polybasic acids such as dodecenyl succinic anhydride and methyl hymic anhydride; (meth) acrylamide, methylene bis- (meth) acrylamide, diethylenetriamine tris (meth) acrylamide, xylylene bis (meta ) Unsaturated monobasic acids such as acrylamide, α-chloroacrylamide and N-2-hydroxyethyl (meth) acrylamide and amides of polyvalent amines; Unsaturated aldehydes such as acrolein; (meth) acrylonitrile, α-chloroacrylonitrile, cyanide Unsaturated nitriles such as vinylidene chloride and allyl cyanide; styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoate Unsaturated aromatic compounds such as acid, vinylphenol, vinylsulfonic acid, 4-vinylbenzenesulfonic acid, vinylbenzyl methyl ether and vinylbenzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; vinylamine, allylamine, N-vinylpyrrolidone And unsaturated amine compounds such as vinyl piperidine; vinyl alcohols such as allyl alcohol and crotyl alcohol; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether and allyl glycidyl ether; maleimide, N-phenylmaleimide And unsaturated imides such as N-cyclohexylmaleimide; indenes such as indene and 1-methylindene; 1,3-butadiene, isoprene and chloroprene Aliphatic monomers such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, and polysiloxane macromonomer having a mono (meth) acryloyl group at the end of the polymer molecular chain; vinyl Chloride, vinylidene chloride, divinyl succinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl group-containing vinyl monomer, polyisocyanate Examples of the compound include vinyl epoxy compounds such as a vinyl urethane compound, a hydroxyl group-containing vinyl monomer, and a polyepoxy compound.
Commercially available products can also be used as the radical polymerizable compound, for example, Kaylad DPHA, DPEA-12, PEG400DA, THE-330, RP-1040, NPGDA, PET30 (manufactured by Nippon Kayaku Co., Ltd.), Aronix M-215. , M-350 (manufactured by Toagosei Co., Ltd.), NK ester A-DPH, A-TMPT, A-DCP, A-HD-N, TMPT, DCP, NPG and HD-N (manufactured by Shin-Nakamura Chemical Co., Ltd.) Can be mentioned.
耐熱性が良好なことから、上記重合性化合物(B)としてラジカル重合性化合物を用いる場合は、下記一般式(II)で表されるエポキシ化合物及び、不飽和一塩基酸との反応によって得られるエポキシ付加物と、多塩基酸無水物とのエステル化反応により得られるエチレン性不飽和化合物を用いることが望ましい。 Since heat resistance is good, when a radical polymerizable compound is used as the polymerizable compound (B), it is obtained by a reaction with an epoxy compound represented by the following general formula (II) and an unsaturated monobasic acid. It is desirable to use an ethylenically unsaturated compound obtained by an esterification reaction between an epoxy adduct and a polybasic acid anhydride.
上記アルキル基及びアリールアルキル基中のアルキレン部分は、不飽和結合、−O−又は−S−で中断されてもよく、R11、R12、R13、R14、R15、R16、R17、R18、R23、R24、R25、R26、R31、R32、R33、R34、R35、R36、R37、R38、及びR39は、隣接するR11、R12、R13、R14、R15、R16、R17、R18、R23、R24、R25、R26、R31、R32、R33、R34、R35、R36、R37、R38、及びR39同士で環を形成してもよい。)
The alkylene moiety in the above alkyl group and arylalkyl group may be interrupted by an unsaturated bond, —O— or —S—, and R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 23 , R 24 , R 25 , R 26 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , and R 39 are adjacent to R 11. R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 23 , R 24 , R 25 , R 26 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , and R 39 may form a ring. )
上記一般式(II)中のMで表される炭素原子数1〜10の炭化水素基としては、メタンジイル、エタンジイル、プロパンジイル、iso−プロパンジイル、ブタンジイル、sec−ブタンジイル、tert−ブタンジイル、iso−ブタンジイル、ペンタンジイル、iso−ペンタンジイル、tert−ペンタンジイル、ヘキサンジイル、ヘプタンジイル、イソヘプタンジイル、t−ヘプタンジイル、n−オクタンジイル、イソオクタンジイル、t−オクタンジイル、2−エチルヘキサンジイル、n−ノナンジイル、n−デカンジイル、トリフルオロメタンジイル、ジフルオロメタンジイル、モノフルオロメタンジイル、ペンタフルオロエタンジイル、テトラフルオロエタンジイル、トリフルオロエタンジイル、ジフルオロエタンジイル、ヘプタフルオロプロパンジイル、ヘキサフルオロプロパンジイル、ペンタフルオロプロパンジイル、テトラフルオロプロパンジイル、トリフルオロプロパンジイル、パーフルオロブタンジイル、シクロプロパンジイル、シクロブタンジイル、シクロペンタンジイル、シクロヘキサンジイル、シクロヘプタンジイル、シクロオクタンジイル、シクロノナンジイル及びシクロデカンジイル等が挙げられる。 Examples of the hydrocarbon group having 1 to 10 carbon atoms represented by M in the general formula (II) include methanediyl, ethanediyl, propanediyl, iso-propanediyl, butanediyl, sec-butanediyl, tert-butanediyl, iso- Butanediyl, pentanediyl, iso-pentanediyl, tert-pentanediyl, hexanediyl, heptanediyl, isoheptanediyl, t-heptanediyl, n-octanediyl, isooctanediyl, t-octanediyl, 2-ethylhexanediyl, n-nonanediyl, n- Decanediyl, trifluoromethanediyl, difluoromethanediyl, monofluoromethanediyl, pentafluoroethanediyl, tetrafluoroethanediyl, trifluoroethanediyl, difluoroethanediyl, Tafluoropropanediyl, hexafluoropropanediyl, pentafluoropropanediyl, tetrafluoropropanediyl, trifluoropropanediyl, perfluorobutanediyl, cyclopropanediyl, cyclobutanediyl, cyclopentanediyl, cyclohexanediyl, cycloheptanediyl, cyclooctane Examples include diyl, cyclononanediyl and cyclodecanediyl.
上記一般式(II)中、R2〜R9で表される炭素原子数1〜20のアルキル基、炭素原子数1〜10のアルコキシ基及びハロゲン原子としては、上記一般式(I)中のR1の説明で例示したものが挙げられる。 In the general formula (II), the alkyl group having 1 to 20 carbon atoms, the alkoxy group having 1 to 10 carbon atoms, and the halogen atom represented by R 2 to R 9 include those in the general formula (I). those exemplified in the explanation of R 1 can be mentioned.
上記一般式(II)中のMである上記式(イ)、(ロ)、(ハ)及び(ニ)で表される群から選ばれる置換基において、R10で表される炭素原子数1〜20のアルキル基及び炭素原子数6〜20のアリール基としては、上記一般式(I)中のR1の説明で例示したものが挙げられる。 In the substituent selected from the group represented by the above formulas (A), (B), (C) and (D), which is M in the general formula (II), the number of carbon atoms represented by R 10 is 1 Examples of the ˜20 alkyl group and the aryl group having 6 to 20 carbon atoms include those exemplified in the description of R 1 in the general formula (I).
上記一般式(II)中のMである上記式(イ)、(ロ)、(ハ)及び(ニ)で表される群から選ばれる置換基において、R11〜R39で表される炭素原子数1〜20のアルキル基、炭素原子数1〜10のアルコキシ基、炭素原子数6〜20のアリール基及びハロゲン原子としては、上記一般式(I)中のR1の説明で例示したものが挙げられ、
R11〜R39で炭素原子数1〜10の脂環式炭化水素基としては、Mの説明で例示したものが挙げられ、
R11〜R39で表される炭素原子数7〜20のアリールアルキル基としては、ベンジル、フェネチル、2−フェニルプロピル、ジフェニルメチル、トリフェニルメチル、スチリル、シンナミル及び4−クロロフェニルメチル等が挙げられ、
R11〜R39で表される炭素数2〜20の複素環基としては、ピロリル、ピリジル、ピリミジル、ピリダジル、ピペラジル、ピペリジル、ピラニル、ピラゾリル、トリアジル、ピロリジル、キノリル、イソキノリル、イミダゾリル、ベンゾイミダゾリル、トリアゾリル、フリル、フラニル、ベンゾフラニル、チエニル、チオフェニル、ベンゾチオフェニル、チアジアゾリル、チアゾリル、ベンゾチアゾリル、オキサゾリル、ベンゾオキサゾリル、イソチアゾリル、イソオキサゾリル、インドリル、ユロリジル、モルフォリニル、チオモルフォリニル、2−ピロリジノン−1−イル、2−ピペリドン−1−イル、2,4−ジオキシイミダゾリジン−3−イル及び2,4−ジオキシオキサゾリジン−3−イル等が挙げられる。
In the substituent selected from the group represented by the above formulas (a), (b), (c) and (d), which is M in the general formula (II), carbon represented by R 11 to R 39 Examples of the alkyl group having 1 to 20 atoms, the alkoxy group having 1 to 10 carbon atoms, the aryl group having 6 to 20 carbon atoms, and the halogen atom are those exemplified in the description of R 1 in the general formula (I). Are mentioned,
Examples of the alicyclic hydrocarbon group having 1 to 10 carbon atoms represented by R 11 to R 39 include those exemplified in the description of M.
Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 11 to R 39 include benzyl, phenethyl, 2-phenylpropyl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl and 4-chlorophenylmethyl. ,
Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R 11 to R 39 include pyrrolyl, pyridyl, pyrimidyl, pyridazyl, piperazyl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolidyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl , Furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, yurolidyl, morpholinyl, thiomorpholinyl, 2-pyrrolidinon-1-yl 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4-dioxyoxazolidine-3-yl, and the like.
上記不飽和一塩基酸とは、構造中に不飽和結合を有し、電離して水素イオンになることのできる水素原子を1分子あたり1個もつ酸を表す。
上記不飽和一塩基酸としては、例えば、アクリル酸、メタクリル酸、クロトン酸、桂皮酸、ソルビン酸及びヒドロキシエチルメタクリレート・マレート、ヒドロキシプロピルメタクリレート・マレート、ヒドロキシプロピルアクリレート・マレート及びジシクロペンタジエン・マレート等が挙げられる。
The unsaturated monobasic acid is an acid having an unsaturated bond in the structure and having one hydrogen atom per molecule that can be ionized to form a hydrogen ion.
Examples of the unsaturated monobasic acid include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid and hydroxyethyl methacrylate / malate, hydroxypropyl methacrylate / malate, hydroxypropyl acrylate / malate, and dicyclopentadiene / malate. Is mentioned.
上記多塩基酸無水物とは、電離して水素イオンになることのできる水素原子を1分子あたり2つ以上持つ多塩基酸の酸無水物を表す。
上記多塩基酸無水物としては、例えば、ビフェニルテトラカルボン酸二無水物、テトラヒドロ無水フタル酸、無水コハク酸、無水マレイン酸、トリメリット酸無水物、ピロメリット酸無水物、2,2'−3,3'−ベンゾフェノンテトラカルボン酸無水物、エチレングリコールビスアンヒドロトリメリテート、グリセロールトリスアンヒドロトリメリテート、ヘキサヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、ナジック酸無水物、メチルナジック酸無水物、トリアルキルテトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸、5−(2,5−ジオキソテトラヒドロフリル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸無水物、トリアルキルテトラヒドロ無水フタル酸−無水マレイン酸付加物、ドデセニル無水コハク酸及び無水メチルハイミック酸等が挙げられる。
The polybasic acid anhydride represents a polybasic acid anhydride having two or more hydrogen atoms per molecule that can be ionized to form hydrogen ions.
Examples of the polybasic acid anhydride include biphenyltetracarboxylic dianhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, 2,2′-3. , 3′-benzophenone tetracarboxylic acid anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, hexahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, nadic acid anhydride, methyl nadic acid anhydride, Trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride-anhydride Maleic acid adduct, dodecenyl anhydride Acid and the like anhydride methylhymic Mick acid.
上記一般式(II)で表されるエポキシ化合物と記不飽和一塩基酸及び上記多塩基酸無水物の反応モル比は、以下の通りとすることが好ましい。
即ち、上記エポキシ化合物のエポキシ基1個に対し、上記不飽和一塩基酸のカルボキシル基が0.1〜1.0個で付加させた構造を有するエポキシ付加物において、該エポキシ付加物の水酸基1個に対し、上記多塩基酸無水物の多塩基酸無水物構造が0.1〜1.0個となる比率となるようにするのが好ましい。
上記エポキシ化合物、上記不飽和一塩基酸及び上記多塩基酸無水物の反応例を下記に示すが、本発明は、下記反応スキーム1に限定されるものではない。
The reaction molar ratio of the epoxy compound represented by the general formula (II) to the unsaturated monobasic acid and the polybasic acid anhydride is preferably as follows.
That is, in the epoxy adduct having a structure in which 0.1 to 1.0 carboxyl groups of the unsaturated monobasic acid are added to one epoxy group of the epoxy compound, the hydroxyl group of the epoxy adduct is 1 It is preferable that the polybasic acid anhydride structure of the polybasic acid anhydride has a ratio of 0.1 to 1.0.
Although the reaction example of the said epoxy compound, the said unsaturated monobasic acid, and the said polybasic acid anhydride is shown below, this invention is not limited to the following reaction scheme 1.
上記一般式(II)で表されるエポキシ化合物としては、R2〜R9が全て水素原子であるものを用いることが、入手しやすさやカーボンブラックを着色剤として添加した場合に高OD値になることから好ましい。また同様の観点から、Mが式(イ)で表される基であり、R11〜R15が水素原子又はフェニル基であるもの、Mが式(ロ)で表される基であり、R16〜R23が水素原子又はフェニル基であるもの、Mが式(ハ)で表される基であり、R24〜R31が水素原子又はフェニル基であるもの、或いは、Mが式(ニ)で表される基であり、R32〜R39が水素原子又はフェニル基であるものを用いることも好ましい。
また上記不飽和一塩基酸としては、炭原子数5以下のものを用いるものが好ましく、特にアクリル酸、メタクリル酸等を用いるものが好ましい。また多塩基酸無水物としては、ベンゼン環又は飽和脂肪環を有するものが好ましく、特にビフェニルテトラカルボン酸ニ無水物、無水フタル酸、テトラヒドロ無水フタル酸及びビフタル酸無水物等を用いたものが好ましい。
As the epoxy compound represented by the general formula (II), it is possible to use a compound in which R 2 to R 9 are all hydrogen atoms, so that it is easy to obtain and has a high OD value when carbon black is added as a colorant. This is preferable. From the same viewpoint, M is a group represented by the formula (A), R 11 to R 15 are hydrogen atoms or phenyl groups, M is a group represented by the formula (B), and R 16 to R 23 are a hydrogen atom or a phenyl group, M is a group represented by the formula (c), R 24 to R 31 are a hydrogen atom or a phenyl group, or M is a formula (ni It is also preferred to use a group represented by formula (II), wherein R 32 to R 39 are a hydrogen atom or a phenyl group.
As the unsaturated monobasic acid, those having 5 or less carbon atoms are preferable, and those using acrylic acid, methacrylic acid or the like are particularly preferable. As the polybasic acid anhydride, those having a benzene ring or a saturated alicyclic ring are preferred, and those using biphenyltetracarboxylic dianhydride, phthalic anhydride, tetrahydrophthalic anhydride, biphthalic anhydride, etc. are particularly preferred. .
上記ラジカル重合性化合物としては、着色剤の分散性、硬化性が良好なことから、下記の製法による生成物が好ましいが、これらに制限されるものではない。
具体的には、例えば、上記一般式(II)で表されるエポキシ化合物として1,1−ビス〔4−(2,3−エポキシプロピルオキシ)フェニル〕インダンを、不飽和一塩基酸としてアクリル酸不飽和一塩基酸としてアクリル酸を多塩基酸無水物としてビフタル酸無水物を選択してなる生成物、
上記一般式(II)で表されるエポキシ化合物として1,1−ビス〔4−(2,3−エポキシプロピルオキシ)フェニル〕インダンを、不飽和一塩基酸としてアクリル酸を多塩基酸無水物としてテトラヒドロ無水フタル酸を選択してなる生成物、
上記一般式(II)で表されるエポキシ化合物として1,1−ビス〔4−(2,3−エポキシプロピルオキシ)フェニル〕インダンを、不飽和一塩基酸としてアクリル酸を多塩基酸としてフタル酸無水物を選択してなる生成物、
上記一般式(II)で表されるエポキシ化合物として1,1−ビス〔4−(2,3−エポキシプロピルオキシ)フェニル〕インダンを、不飽和一塩基酸としてアクリル酸を多塩基酸無水物としてビフタル酸無水物及びテトラヒドロ無水フタル酸を選択してなる生成物、及び
上記一般式(II)で表されるエポキシ化合物として1,1−ビス〔4−(2,3−エポキシプロピルオキシ)フェニル〕−3−フェニルインダンを、不飽和一塩基酸としてアクリル酸を多塩基酸無水物としてビフタル酸無水物及びテトラヒドロ無水フタル酸を選択してなる生成物等が挙げられる。
The radical polymerizable compound is preferably a product produced by the following production method because of good dispersibility and curability of the colorant, but is not limited thereto.
Specifically, for example, 1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane is used as the epoxy compound represented by the general formula (II), and acrylic acid is used as the unsaturated monobasic acid. A product obtained by selecting acrylic acid as unsaturated monobasic acid and biphthalic anhydride as polybasic acid anhydride,
1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane as an epoxy compound represented by the above general formula (II), acrylic acid as a polybasic acid anhydride as an unsaturated monobasic acid A product formed by selecting tetrahydrophthalic anhydride,
1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane as an epoxy compound represented by the above general formula (II), acrylic acid as an unsaturated monobasic acid, and phthalic acid as a polybasic acid A product formed by selecting an anhydride,
1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane as an epoxy compound represented by the above general formula (II), acrylic acid as a polybasic acid anhydride as an unsaturated monobasic acid Products obtained by selecting biphthalic anhydride and tetrahydrophthalic anhydride, and 1,1-bis [4- (2,3-epoxypropyloxy) phenyl] as an epoxy compound represented by the above general formula (II) Examples thereof include a product obtained by selecting -3-phenylindane as an unsaturated monobasic acid, acrylic acid as a polybasic acid anhydride, biphthalic anhydride and tetrahydrophthalic anhydride.
また、上記ラジカル重合性化合物としては、アクリル酸エステルの共重合体や、フェノール及び/又はクレゾールノボラックエポキシ樹脂、多官能エポキシ基を有するポリフェニルメタン型エポキシ樹脂を用いることもできる。 As the radical polymerizable compound, a copolymer of acrylic acid ester, a phenol and / or cresol novolac epoxy resin, or a polyphenylmethane type epoxy resin having a polyfunctional epoxy group may be used.
上記ラジカル重合性化合物は、酸価を有する化合物を用いた場合、本発明の硬化性組成物にアルカリ現像性を付与することができる。上記酸価を有する化合物を用いる場合、その使用量は上記ラジカル重合性化合物中、50〜99質量%となるようにすることが好ましい。
また、上記酸価を有する化合物は、更に単官能又は多官能エポキシ化合物を反応させることにより酸価を調整してから用いることもできる。上記酸価を有する化合物の酸価を調整することにより、硬化性組成物のアルカリ現像性を改良することができる。上記酸価を有する化合物(即ちアルカリ現像性を付与するラジカル重合性化合物)は、固形分の酸価が5〜120mgKOH/gの範囲であることが好ましく、単官能又は多官能エポキシ化合物の使用量は、上記酸価を満たすように選択するのが好ましい。
The said radically polymerizable compound can provide alkali developability to the curable composition of this invention, when the compound which has an acid value is used. When using the compound which has the said acid value, it is preferable to make the usage-amount become 50-99 mass% in the said radically polymerizable compound.
The compound having the acid value can be used after adjusting the acid value by further reacting with a monofunctional or polyfunctional epoxy compound. The alkali developability of the curable composition can be improved by adjusting the acid value of the compound having the acid value. The compound having an acid value (that is, a radically polymerizable compound imparting alkali developability) preferably has a solid acid value in the range of 5 to 120 mgKOH / g, and the amount of monofunctional or polyfunctional epoxy compound used. Is preferably selected so as to satisfy the above acid value.
上記単官能エポキシ化合物としては、グリシジルメタクリレート、メチルグリシジルエーテル、エチルグリシジルエーテル、プロピルグリシジルエーテル、イソプロピルグリシジルエーテル、ブチルグリシジルエーテル、イソブチルグリシジルエーテル、t−ブチルグリシジルエーテル、ペンチルグリシジルエーテル、ヘキシルグリシジルエーテル、ヘプチルグリシジルエーテル、オクチルグリシジルエーテル、ノニルグリシジルエーテル、デシルグリシジルエーテル、ウンデシルグリシジルエーテル、ドデシルグリシジルエーテル、トリデシルグリシジルエーテル、テトラデシルグリシジルエーテル、ペンタデシルグリシジルエーテル、ヘキサデシルグリシジルエーテル、2−エチルヘキシルグリシジルエーテル、アリルグリシジルエーテル、プロパルギルグリシジルエーテル、p−メトキシエチルグリシジルエーテル、フェニルグリシジルエーテル、p−メトキシグリシジルエーテル、p−ブチルフェノールグリシジルエーテル、クレジルグリシジルエーテル、2−メチルクレジルグリシジルエーテル、4−ノニルフェニルグリシジルエーテル、ベンジルグリシジルエーテル、p−クミルフェニルグリシジルエーテル、トリチルグリシジルエーテル、2,3−エポキシプロピルメタクリレート、エポキシ化大豆油、エポキシ化アマニ油、グリシジルブチレート、ビニルシクロヘキサンモノオキシド、1,2−エポキシ−4−ビニルシクロヘキサン、スチレンオキシド、ピネンオキシド、メチルスチレンオキシド、シクロヘキセンオキシド、プロピレンオキシド、上記化合物No.B2及びNo.B3等が挙げられる。 Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl. Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, 2-ethylhexyl glycidyl ether, Allyl glycidylate , Propargyl glycidyl ether, p-methoxyethyl glycidyl ether, phenyl glycidyl ether, p-methoxy glycidyl ether, p-butylphenol glycidyl ether, cresyl glycidyl ether, 2-methyl cresyl glycidyl ether, 4-nonylphenyl glycidyl ether, benzyl glycidyl Ether, p-cumylphenyl glycidyl ether, trityl glycidyl ether, 2,3-epoxypropyl methacrylate, epoxidized soybean oil, epoxidized linseed oil, glycidyl butyrate, vinylcyclohexane monooxide, 1,2-epoxy-4-vinyl Cyclohexane, styrene oxide, pinene oxide, methyl styrene oxide, cyclohexene oxide, propylene oxide, the above-mentioned compound no. B2 and No. B3 etc. are mentioned.
上記多官能エポキシ化合物としては、ビスフェノール型エポキシ化合物及びグリシジルエーテル類からなる群から選択される一種以上の化合物を用いると、特性の一層良好な硬化性組成物を得ることができるので好ましい。
上記ビスフェノール型エポキシ化合物としては、上記一般式(II)で表されるビスフェノール型エポキシ化合物を用いることができる他、例えば、水添ビスフェノール型エポキシ化合物等のビスフェノール型エポキシ化合物も用いることができる。
また上記グリシジルエーテル類としては、エチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、1,4−ブタンジオールジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、1,8−オクタンジオールジグリシジルエーテル、1,10−デカンジオールジグリシジルエーテル、2,2−ジメチル−1,3−プロパンジオールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、トリエチレングリコールジグリシジルエーテル、テトラエチレングリコールジグリシジルエーテル、ヘキサエチレングリコールジグリシジルエーテル、1,4−シクロヘキサンジメタノールジグリシジルエーテル、1,1,1−トリ(グリシジルオキシメチル)プロパン、1,1,1−トリ(グリシジルオキシメチル)エタン、1,1,1−トリ(グリシジルオキシメチル)メタン及び1,1,1,1−テトラ(グリシジルオキシメチル)メタン等を用いることができる。
その他、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物;3,4−エポキシ−6−メチルシクロヘキシルメチル−3,4−エポキシ−6−メチルシクロヘキサンカルボキシレート、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート及び1−エポキシエチル−3,4−エポキシシクロヘキサン等の脂環式エポキシ化合物;フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル及びダイマー酸グリシジルエステル等のグリシジルエステル類;テトラグリシジルジアミノジフェニルメタン、トリグリシジルP−アミノフェノール及びN,N−ジグリシジルアニリン等のグリシジルアミン類;1,3−ジグリシジル−5,5−ジメチルヒダントイン及びトリグリシジルイソシアヌレート等の複素環式エポキシ化合物;ジシクロペンタジエンジオキシド等のジオキシド化合物;ナフタレン型エポキシ化合物;トリフェニルメタン型エポキシ化合物及びジシクロペンタジエン型エポキシ化合物等を用いることもできる。
As the polyfunctional epoxy compound, it is preferable to use one or more compounds selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers because a curable composition with better characteristics can be obtained.
As the bisphenol-type epoxy compound, a bisphenol-type epoxy compound represented by the general formula (II) can be used, and for example, a bisphenol-type epoxy compound such as a hydrogenated bisphenol-type epoxy compound can also be used.
Examples of the glycidyl ethers include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1,10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl Ether, 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-to (Glycidyloxymethyl) ethane, 1,1,1-tri (glycidyloxymethyl) methane, and 1,1,1,1- tetra (glycidyloxymethyl) can be used such as methane.
Other novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxies such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate and 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as phthalic acid diglycidyl ester, tetrahydrophthalic acid diglycidyl ester and dimer glycidyl ester; tetraglycidyldia Glycidylamines such as nodiphenylmethane, triglycidyl P-aminophenol and N, N-diglycidylaniline; heterocyclic epoxy compounds such as 1,3-diglycidyl-5,5-dimethylhydantoin and triglycidyl isocyanurate; Dioxide compounds such as pentadiene dioxide; naphthalene type epoxy compounds; triphenylmethane type epoxy compounds and dicyclopentadiene type epoxy compounds can also be used.
・カチオン重合性化合物について
上記カチオン重合性化合物としては、エポキシ化合物、オキセタン化合物及びビニルエーテル化合物等が挙げられる。
-About cationically polymerizable compound As said cationically polymerizable compound, an epoxy compound, an oxetane compound, a vinyl ether compound, etc. are mentioned.
上記エポキシ化合物としては、例えば、メチルグリシジルエーテル、2−エチルヘキシルグリシジルエーテル、ブチルグリシジルエーテル、デシルグリシジルエーテル、C12〜13混合アルキルグリシジルエーテル、フェニル−2−メチルグリシジルエーテル、セチルグリシジルエーテル、ステアリルグリシジルエーテル、p−sec−ブチルフェニルグリシジルエーテル、p−tert−ブチルフェニルグリシジルエーテル、グリシジルメタクリレート、イソプロピルグリシジルエーテル、アリルグリシジルエーテル、エチルグリシジルエーテル、2−メチルオクチルグリシジルエーテル、フェニルグリシジルエーテル、4−n−ブチルフェニルグリシジルエーテル、4−フェニルフェノールグリシジルエーテル、クレジルグリシジルエーテル、ジブロモクレジルグリシジルエーテル、デシルグリシジルエーテル、メトキシポリエチレングリコールモノグリシジルエーテル、エトキシポリエチレングリコールモノグリシジルエーテル、ブトキシポリエチレングリコールモノグリシジルエーテル、フェノキシポリエチレングリコールモノグリシジルエーテル、ジブロモフェニルグリシジルエーテル、1,4−ブタンジオールジグリシジルエーテル、1,5−ペンタンジオールジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、1,1,2,2−テトラキス(グリシジルオキシフェニル)エタン及びペンタエリスリトールテトラグリシジルエーテル等のグリシジルエーテル化物;グリシジルアセテート、グリシジルステアレート等のグリシジルエステル類;2−(3,4−エポキシシクロヘキシル−5,5−スピロ−3,4−エポキシ)シクロヘキサン−メタジオキサン、メチレンビス(3,4−エポキシシクロヘキサン)、プロパン−2,2−ジイル−ビス(3,4−エポキシシクロヘキサン)、2,2−ビス(3,4−エポキシシクロヘキシル)プロパン、エチレンビス(3,4−エポキシシクロヘキサンカルボキシレート)、ビス(3,4−エポキシシクロヘキシルメチル)アジペート、3,4−エポキシシクロヘキシルメチル 3,4−エポキシシクロヘキサンカルボキシレート、3,4−エポキシ−1−メチルシクロヘキシル 3,4−エポキシ−1−メチルヘキサンカルボキシレート、6−メチル−3,4−エポキシシクロヘキシルメチル 6−メチル−3,4−エポキシシクロヘキサンカルボキシレート、3,4−エポキシ−3−メチルシクロヘキシルメチル 3,4−エポキシ−3−メチルシクロヘキサンカルボキシレート、3,4−エポキシ−5−メチルシクロヘキシルメチル 3,4−エポキシ−5−メチルシクロヘキサンカルボキシレート、1−エポキシエチル−3,4−エポキシシクロヘキサン、1,2−エポキシ−2−エポキシエチルシクロヘキサン、ジシクロペンタジエンジエポキサイド、3,4−エポキシ−6−メチルシクロヘキシルカルボキシレート、α−ピネンオキシド、スチレンオキシド、シクロヘキセンオキサイド及びシクロペンテンオキサイド等のエポキシシクロアルキル型化合物及びN−グリシジルフタルイミド等が挙げられる。 Examples of the epoxy compound include methyl glycidyl ether, 2-ethylhexyl glycidyl ether, butyl glycidyl ether, decyl glycidyl ether, C12-13 mixed alkyl glycidyl ether, phenyl-2-methyl glycidyl ether, cetyl glycidyl ether, stearyl glycidyl ether, p-sec-butylphenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, glycidyl methacrylate, isopropyl glycidyl ether, allyl glycidyl ether, ethyl glycidyl ether, 2-methyloctyl glycidyl ether, phenyl glycidyl ether, 4-n-butylphenyl Glycidyl ether, 4-phenylphenol glycidyl ether, cresyl glycidyl ether Ter, dibromocresyl glycidyl ether, decyl glycidyl ether, methoxy polyethylene glycol monoglycidyl ether, ethoxy polyethylene glycol monoglycidyl ether, butoxy polyethylene glycol monoglycidyl ether, phenoxy polyethylene glycol monoglycidyl ether, dibromophenyl glycidyl ether, 1,4-butane Diol diglycidyl ether, 1,5-pentanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,1,2,2-tetrakis (glycidyloxyphenyl) ethane and pentaerythritol Glycidyl ethers such as tetraglycidyl ether; glycidyl acetate, glycidyl ether Glycidyl esters such as distearate; 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane-metadioxane, methylenebis (3,4-epoxycyclohexane), propane-2, 2-diyl-bis (3,4-epoxycyclohexane), 2,2-bis (3,4-epoxycyclohexyl) propane, ethylenebis (3,4-epoxycyclohexanecarboxylate), bis (3,4-epoxycyclohexyl) Methyl) adipate, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl 3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4 -Epoxycyclohexylmethyl 6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl 3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl 3, 4-epoxy-5-methylcyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, dicyclopentadiene diepoxide, 3,4-epoxy-6-methyl Examples thereof include epoxy cycloalkyl type compounds such as cyclohexyl carboxylate, α-pinene oxide, styrene oxide, cyclohexene oxide and cyclopentene oxide, and N-glycidyl phthalimide.
また上記エポキシ化合物としては、エポキシ化ポリオレフィンを用いることもできる。エポキシ化ポリオレフィンとは、ポリオレフィンをエポキシ基含有単量体で変性して、エポキシ基を導入したポリオレフィンである。エチレン又は炭素数3〜20のα−オレフィン、エポキシ基含有単量体、及び必要に応じて他のモノマーとを、共重合法及びグラフト法のいずれかにより共重合させることによって製造することができる。エチレン又は炭素数3〜20のα−オレフィン、エポキシ基含有単量体及び他のモノマーは、それぞれ単独で重合させてもよく、他の単量体と複数で重合させてもよい。また、末端に水酸基を有する非共役のポリブタジエンの二重結合を、過酢酸法によりエポキシ化して得ることもでき、分子内に水酸基を持つものを使用してもよい。また、水酸基をイソシアネートでウレタン化し、ここに1級水酸基含有エポキシ化合物を反応させてエポキシ基を導入することもできる。 Moreover, an epoxidized polyolefin can also be used as the epoxy compound. The epoxidized polyolefin is a polyolefin having an epoxy group introduced by modifying the polyolefin with an epoxy group-containing monomer. It can be produced by copolymerizing ethylene or an α-olefin having 3 to 20 carbon atoms, an epoxy group-containing monomer, and, if necessary, another monomer by either a copolymerization method or a graft method. . Ethylene or an α-olefin having 3 to 20 carbon atoms, an epoxy group-containing monomer, and other monomers may be polymerized alone or in combination with other monomers. Moreover, the double bond of the nonconjugated polybutadiene which has a hydroxyl group at the terminal can be obtained by epoxidation by the peracetic acid method, and those having a hydroxyl group in the molecule may be used. It is also possible to urethanize a hydroxyl group with an isocyanate and introduce an epoxy group by reacting with a primary hydroxyl group-containing epoxy compound.
上記エチレン又は炭素数3〜20のα−オレフィンとしては、エチレン、プロピレン、ブチレン、イソブチレン、1,3−ブタジエン、1,4−ブタジエン、1,3−ペンタジエン、2,3−ジメチル−1,3−ブタジエン、ピペリレン、3−ブチル−1,3−オクタジエン及びイソプレン等が挙げられる。 Examples of the ethylene or α-olefin having 3 to 20 carbon atoms include ethylene, propylene, butylene, isobutylene, 1,3-butadiene, 1,4-butadiene, 1,3-pentadiene, and 2,3-dimethyl-1,3. -Butadiene, piperylene, 3-butyl-1,3-octadiene, isoprene and the like.
上記エポキシ基含有単量体としては、たとえばα,β−不飽和酸のグリシジルエステル、ビニルベンジルグリシジルエーテル及びアリルグリシジルエーテル等が挙げられる。α,β−不飽和酸のグリシジルエステルとしては、具体的にはアクリル酸グリシジル、メタクリル酸グリシジル及びエタクリル酸グリシジル等が挙げられ、特にメタクリル酸グリシジルが好ましい。 Examples of the epoxy group-containing monomer include glycidyl ester of α, β-unsaturated acid, vinyl benzyl glycidyl ether, and allyl glycidyl ether. Specific examples of the glycidyl ester of α, β-unsaturated acid include glycidyl acrylate, glycidyl methacrylate and glycidyl ethacrylate, and glycidyl methacrylate is particularly preferable.
上記他のモノマーとしては、塩化ビニル、塩化ビニリデン、フッ化ビニリデン及びテトラフルオロエチレン等の不飽和脂肪族炭化水素;(メタ)アクリル酸、α―クロルアクリル酸、イタコン酸、マレイン酸、シトラコン酸、フマル酸、ハイミック酸、クロトン酸、イソクロトン酸、ビニル酢酸、アリル酢酸、桂皮酸、ソルビン酸、メサコン酸、コハク酸モノ[2−(メタ)アクリロイロキシエチル]、フタル酸モノ[2−(メタ)アクリロイロキシエチル]、ω−カルボキシポリカプロラクトンモノ(メタ)アクリレート等の両末端にカルボキシ基と水酸基とを有するポリマーのモノ(メタ)アクリレート、ヒドロキシエチル(メタ)アクリレート・マレート、ヒドロキシプロピル(メタ)アクリレート・マレート、ジシクロペンタジエン・マレート及び1個のカルボキシル基と2個以上の(メタ)アクリロイル基とを有する多官能(メタ)アクリレート等の不飽和多塩基酸;(メタ)アクリル酸−2−ヒドロキシエチル、(メタ)アクリル酸−2−ヒドロキシプロピル、(メタ)アクリル酸メチル、(メタ)アクリル酸ブチル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸−t−ブチル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸n−オクチル、(メタ)アクリル酸イソオクチル、(メタ)アクリル酸イソノニル、(メタ)アクリル酸ステアリル、(メタ)アクリル酸ラウリル、(メタ)アクリル酸メトキシエチル、(メタ)アクリル酸ジメチルアミノメチル、(メタ)アクリル酸ジメチルアミノエチル、(メタ)アクリル酸アミノプロピル、(メタ)アクリル酸ジメチルアミノプロピル、(メタ)アクリル酸エトキシエチル、(メタ)アクリル酸ポリ(エトキシ)エチル、(メタ)アクリル酸ブトキシエトキシエチル、(メタ)アクリル酸エチルヘキシル、(メタ)アクリル酸フェノキシエチル、(メタ)アクリル酸テトラヒドロフリル、(メタ)アクリル酸ビニル、(メタ)アクリル酸アリル、(メタ)アクリル酸ベンジル、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、1,4−ブタンジオールジ(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、トリメチロールエタントリ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、トリシクロデカンジメチロールジ(メタ)アクリレート、トリ[(メタ)アクリロイルエチル]イソシアヌレート及びポリエステル(メタ)アクリレートオリゴマー等の不飽和一塩基酸及び多価アルコール又は多価フェノールのエステル;(メタ)アクリル酸亜鉛、(メタ)アクリル酸マグネシウム等の不飽和多塩基酸の金属塩;マレイン酸無水物、イタコン酸無水物、シトラコン酸無水物、メチルテトラヒドロ無水フタル酸、テトラヒドロ無水フタル酸、トリアルキルテトラヒドロ無水フタル酸、5−(2,5−ジオキソテトラヒドロフリル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸無水物、トリアルキルテトラヒドロ無水フタル酸−無水マレイン酸付加物、ドデセニル無水コハク酸及び無水メチルハイミック酸等の不飽和多塩基酸の酸無水物;(メタ)アクリルアミド、メチレンビス−(メタ)アクリルアミド、ジエチレントリアミントリス(メタ)アクリルアミド、キシリレンビス(メタ)アクリルアミド、α−クロロアクリルアミド、N−2−ヒドロキシエチル(メタ)アクリルアミド等の不飽和一塩基酸及び多価アミンのアミド;アクロレイン等の不飽和アルデヒド;(メタ)アクリロニトリル、α−クロロアクリロニトリル、シアン化ビニリデン、シアン化アリル等の不飽和ニトリル;スチレン、4−メチルスチレン、4−エチルスチレン、4−メトキシスチレン、4−ヒドロキシスチレン、4−クロロスチレン、ジビニルベンゼン、ビニルトルエン、ビニル安息香酸、ビニルフェノール、ビニルスルホン酸、4−ビニルベンゼンスルホン酸、ビニルベンジルメチルエーテル及びビニルナフタレン等の不飽和芳香族化合物;メチルビニルケトン等の不飽和ケトン;ビニルアミン、アリルアミン、N−ビニルピロリドン及びビニルピペリジン等の不飽和アミン化合物;アリルアルコール及びクロチルアルコール等のビニルアルコール;ビニルメチルエーテル、ビニルエチルエーテル、n−ブチルビニルエーテル及びイソブチルビニルエーテル等のビニルエーテル;マレイミド、N−フェニルマレイミド及びN−シクロヘキシルマレイミド等の不飽和イミド類;インデン及び1−メチルインデン等のインデン類;ポリスチレン、ポリメチル(メタ)アクリレート、ポリ−n−ブチル(メタ)アクリレート及びポリシロキサン等の重合体分子鎖の末端にモノ(メタ)アクリロイル基を有するマクロモノマー類;ビニルクロリド、ビニリデンクロリド、ジビニルスクシナート、ジアリルフタラート、トリアリルホスファート、トリアリルイソシアヌラート、ビニルチオエーテル、ビニルイミダゾール、ビニルオキサゾリン、ビニルカルバゾール、ビニルピロリドン、ビニルピリジン、水酸基含有ビニルモノマー及びポリイソシアネート化合物のビニルウレタン化合物、水酸基含有ビニルモノマー及びポリエポキシ化合物のビニルエポキシ化合物、ペンタエリスリトールトリアクリレート及びジペンタエリスリトールペンタアクリレート等の水酸基含有多官能アクリレート;トリレンジイソシアネート及びヘキサメチレンジイソシアネート等の多官能イソシアネートの反応物;ペンタエリスリトールトリアクリレート及びジペンタエリスリトールペンタアクリレート等の水酸基含有多官能アクリレートと無水コハク酸、無水フタル酸及びテトラヒドロ無水フタル酸等の二塩基酸無水物の反応物である酸価を有する多官能アクリレートが挙げられる。 Examples of the other monomers include unsaturated aliphatic hydrocarbons such as vinyl chloride, vinylidene chloride, vinylidene fluoride and tetrafluoroethylene; (meth) acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, Fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinyl acetic acid, allyl acetic acid, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meta ) Acryloyloxyethyl], ω-carboxypolycaprolactone mono (meth) acrylate, etc., polymers having a carboxy group and a hydroxyl group at both ends, hydroxy (meth) acrylate / malate, hydroxypropyl (meth) ) Acrylate / malate, dicyclopentadiene / ma And unsaturated polybasic acids such as polyfunctional (meth) acrylates having one carboxyl group and two or more (meth) acryloyl groups; (meth) acrylic acid-2-hydroxyethyl, (meth) acrylic 2-hydroxypropyl, methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, (t-butyl) (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylic acid n-octyl, isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, ( Dimethylaminoethyl (meth) acrylate, aminopropyl (meth) acrylate, di (meth) acrylate Methylaminopropyl, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (meth) acrylate, ethylhexyl (meth) acrylate, phenoxyethyl (meth) acrylate, (meth) Tetrahydrofuryl acrylate, vinyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, Polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, trimethylol etanthate (Meth) acrylate, trimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, tricyclo Unsaturated monobasic acids such as decane dimethylol di (meth) acrylate, tri [(meth) acryloylethyl] isocyanurate and polyester (meth) acrylate oligomers and esters of polyhydric alcohols or polyphenols; zinc (meth) acrylate , Metal salts of unsaturated polybasic acids such as magnesium (meth) acrylate; maleic anhydride, itaconic anhydride, citraconic anhydride, methyltetrahydrophthalic anhydride, tetrahydroanhydride Talic acid, trialkyltetrahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride Adducts, anhydrides of unsaturated polybasic acids such as dodecenyl succinic anhydride and methyl hymic anhydride; (meth) acrylamide, methylene bis- (meth) acrylamide, diethylenetriamine tris (meth) acrylamide, xylylene bis (meth) acrylamide, Unsaturated monobasic acids such as α-chloroacrylamide and N-2-hydroxyethyl (meth) acrylamide and amides of polyvalent amines; Unsaturated aldehydes such as acrolein; (meth) acrylonitrile, α-chloroacrylonitrile, vinylidene cyanide, cyan Unsaturated nitriles such as allyl; styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinylphenol, vinylsulfonic acid Unsaturated aromatic compounds such as 4-vinylbenzenesulfonic acid, vinylbenzyl methyl ether and vinylnaphthalene; unsaturated ketones such as methyl vinyl ketone; unsaturated amine compounds such as vinylamine, allylamine, N-vinylpyrrolidone and vinylpiperidine; Vinyl alcohols such as allyl alcohol and crotyl alcohol; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether and isobutyl vinyl ether; maleimide, N-phenylmaleimi And unsaturated imides such as N-cyclohexylmaleimide; indenes such as indene and 1-methylindene; polymer molecular chains such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate and polysiloxane Macromonomers having a mono (meth) acryloyl group at the end thereof; vinyl chloride, vinylidene chloride, divinyl succinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, Vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl group-containing vinyl monomers and vinyl isocyanate compounds of polyisocyanate compounds, hydroxyl group-containing vinyl monomers and vinyl epoxy compounds of polyepoxy compounds, Hydroxyl-containing polyfunctional acrylates such as intererythritol triacrylate and dipentaerythritol pentaacrylate; reaction products of polyfunctional isocyanates such as tolylene diisocyanate and hexamethylene diisocyanate; hydroxyl-containing polyfunctionals such as pentaerythritol triacrylate and dipentaerythritol pentaacrylate A polyfunctional acrylate having an acid value, which is a reaction product of an acrylate and a dibasic acid anhydride such as succinic anhydride, phthalic anhydride, and tetrahydrophthalic anhydride.
上記エポキシ化ポリオレフィンとしては、市販品を用いることもでき、例えば、エポリードPB3600、エポリードPB4700(ダイセル社製);BF−1000、FC−3000(ADEKA社製);ボンドファースト2C、ボンドファーストE、ボンドファーストCG5001、ボンドファーストCG5004、ボンドファースト2B、ボンドファースト7B、ボンドファースト7L、ボンドファースト7M、ボンドファーストVC40(住友化学社製);JP−100、JP−200(日本曹達社製);Poly bd R−45HT、Poly bd R−15HT(出光興産社製)及びRicon657(アルケマ社製)等が挙げられる。 Commercially available products can also be used as the epoxidized polyolefin, for example, Epolide PB3600, Epolide PB4700 (manufactured by Daicel); BF-1000, FC-3000 (manufactured by ADEKA); Bond First 2C, Bond First E, Bond First CG5001, BondFirst CG5004, BondFirst 2B, BondFirst 7B, BondFirst 7L, BondFirst 7M, BondFirst VC40 (manufactured by Sumitomo Chemical); JP-100, JP-200 (manufactured by Nippon Soda Co., Ltd.); Poly bd R -45HT, Poly bd R-15HT (made by Idemitsu Kosan Co., Ltd.), Ricon657 (made by Arkema Co., Ltd.) and the like.
耐熱性が良好なことから、上記エポキシ化合物としては、上記一般式(II)で表されるカルド骨格を有する化合物を使用することがより好ましい。 From the viewpoint of good heat resistance, it is more preferable to use a compound having a cardo skeleton represented by the general formula (II) as the epoxy compound.
上記オキセタン化合物としては、例えば、3,7−ビス(3−オキセタニル)−5−オキサ−ノナン、1,4−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]ベンゼン、1,2−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]エタン、1,3−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]プロパン、エチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、トリエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、テトラエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、1,4−ビス(3−エチル−3−オキセタニルメトキシ)ブタン、1,6−ビス(3−エチル−3−オキセタニルメトキシ)ヘキサン、3―エチル―3−[(フェノキシ)メチル]オキセタン、3―エチル―3−(ヘキシロキシメチル)オキセタン、3―エチル―3−(2−エチルヘキシロキシメチル)オキセタン、3―エチル―3−(ヒドロキシメチル)オキセタン及び3―エチル―3−(クロロメチル)オキセタン等が挙げられる。 Examples of the oxetane compound include 3,7-bis (3-oxetanyl) -5-oxa-nonane, 1,4-bis [(3-ethyl-3-oxetanylmethoxy) methyl] benzene, 1,2-bis. [(3-ethyl-3-oxetanylmethoxy) methyl] ethane, 1,3-bis [(3-ethyl-3-oxetanylmethoxy) methyl] propane, ethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, Triethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, tetraethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, 1,4-bis (3-ethyl-3-oxetanylmethoxy) butane, , 6-Bis (3-ethyl-3-oxetanylmethoxy) hexane, 3-ethyl-3- [ Phenoxy) methyl] oxetane, 3-ethyl-3- (hexyloxymethyl) oxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (hydroxymethyl) oxetane and 3-ethyl -3- (Chloromethyl) oxetane and the like.
上記ビニルエーテル化合物としては、例えば、ジエチレングリコールモノビニルエーテル、トリエチレングリコールジビニルエーテル、n−ドデシルビニルエーテル、シクロヘキシルビニルエーテル、2−エチルヘキシルビニルエーテル、2−クロロエチルビニルエーテル、エチルビニルエーテル、イソブチルビニルエーテル、トリエチレングリコールビニルエーテル、2−ヒドロキシエチルビニルエーテル、4−ヒドロキシブチルビニルエーテル、1,6−シクロヘキサンジメタノールモノビニルエーテル、エチレングリコールジビニルエーテル、1,4−ブタンジオールジビニルエーテル及び1,6−シクロヘキサンジメタノールジビニルエーテル等が挙げられる。 Examples of the vinyl ether compound include diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, 2-chloroethyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, triethylene glycol vinyl ether, 2- Examples thereof include hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 1,6-cyclohexanedimethanol monovinyl ether, ethylene glycol divinyl ether, 1,4-butanediol divinyl ether and 1,6-cyclohexanedimethanol divinyl ether.
上記カチオン重合性化合物としては、市販品のものを用いることができ、例えば、エポライト40E、1500NP、1600、80MF、4000及び3002(共栄社化学社製);アデカグリシロールED−503、ED−503D、ED−503G、ED−523T、ED−513、ED−501、ED−502、ED−509、ED−518、ED−529、アデカレジンEP−4000、EP−4005、EP−4080及びEP−4085(ADEKA社製);デナコールEX−201、EX−203、EX−211、EX−212、EX−221、EX−251、EX−252、EX−711、EX−721、デナコールEX−111、EX−121、EX−141、EX−142、EX−145、EX−146、EX−147、EX−171、EX−192及びEX−731(ナガセケムテックス社製);EHPE−3150、セロキサイド2021P、2081、2000及び3000(ダイセル社製);エピオールM、EH、L−41、SK、SB、TB及びOH(日油社製);エポライトM−1230及び100MF(共栄社化学社製);アロンオキセタンOXT−121、OXT−221、EXOH、POX、OXA、OXT−101、OXT−211及びOXT−212(東亞合成社製)、エタナコールOXBP及びOXTP(宇部興産社製);2−ヒドロキシエチルビニルエーテル、ジエチレングリコールモノビニルエーテル及び4−ヒドロキシブチルビニルエーテル(丸善石油化学社製);デナコールEX−121、EX−141、EX−142、EX−145、EX−146、EX−147、EX−201、EX−203、EX−711、EX−721、オンコートEX−1020、EX−1030、EX−1040、EX−1050、EX−1051、EX−1010、EX−1011及び1012(ナガセケムテックス社製);オグソールPG−100、EG−200、EG−210及びEG−250(大阪ガスケミカル社製);HP4032、HP4032D及びHP4700(DIC社製);ESN−475V(東都化成社製);エピコートYX8800(三菱化学社製);マープルーフG−0105SA及びG−0130SP(日油社製);エピクロンN−665及びHP−7200(DIC社製);EOCN−1020、EOCN−102S、EOCN−103S、EOCN−104S、XD−1000、NC−3000、EPPN−501H、EPPN−501HY、EPPN−502H及びNC−7000L(日本化薬社製);等が挙げられる。 Commercially available products can be used as the cationic polymerizable compound, such as Epolite 40E, 1500NP, 1600, 80MF, 4000 and 3002 (manufactured by Kyoeisha Chemical Co., Ltd.); Adekaglycilol ED-503, ED-503D, ED-503G, ED-523T, ED-513, ED-501, ED-502, ED-509, ED-518, ED-529, Adeka Resin EP-4000, EP-4005, EP-4080 and EP-4085 (ADEKA Denacol EX-201, EX-203, EX-211, EX-212, EX-221, EX-251, EX-252, EX-711, EX-721, Denacol EX-111, EX-121, EX-141, EX-142, EX-145, EX-146, EX-14 , EX-171, EX-192 and EX-731 (manufactured by Nagase ChemteX); EHPE-3150, Celoxide 2021P, 2081, 2000 and 3000 (manufactured by Daicel); Epiol M, EH, L-41, SK, SB , TB and OH (manufactured by NOF Corporation); Epolite M-1230 and 100MF (manufactured by Kyoeisha Chemical Co., Ltd.); Aron Oxetane OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211 and OXT- 212 (manufactured by Toagosei Co., Ltd.), etanacol OXBP and OXTP (manufactured by Ube Industries); 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether and 4-hydroxybutyl vinyl ether (manufactured by Maruzen Petrochemical Co., Ltd.); Denacol EX-121, EX-141 , EX-142, E -145, EX-146, EX-147, EX-201, EX-203, EX-711, EX-721, on-coat EX-1020, EX-1030, EX-1040, EX-1050, EX-1051, EX -1010, EX-1011 and 1012 (manufactured by Nagase ChemteX); Ogsol PG-100, EG-200, EG-210 and EG-250 (manufactured by Osaka Gas Chemical Company); HP4032, HP4032D and HP4700 (manufactured by DIC) ESN-475V (manufactured by Tohto Kasei Co., Ltd.); Epicort YX8800 (manufactured by Mitsubishi Chemical); Marproof G-0105SA and G-0130SP (manufactured by NOF Corporation); Epicron N-665 and HP-7200 (manufactured by DIC); EOCN-1020, EOCN-102S, EOCN-103S, EOCN 104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H and NC-7000L (manufactured by Nippon Kayaku Co., Ltd.); and the like.
本発明の硬化性組成物において、重合性化合物(B)の含有量は、特に限定されるものではないが、アリルシラン化合物(A)、重合性化合物(B)及び重合開始剤(C)の合計100質量部に対して、硬化性が良好なことから好ましくは、40〜99質量部、より好ましくは、50〜95質量部である。重合性化合物(B)の含有量が、40質量部より小さいと硬化性が劣り、99質量部より大きいと、密着性が劣る。
例えば膜厚1〜3μmの硬化膜を形成する場合には、重合性化合物(B)の含有量は、アリルシラン化合物(A)、重合性化合物(B)及び重合開始剤(C)の合計100質量部に対して、好ましくは、40〜99質量部、より好ましくは、50〜95質量部である。
In the curable composition of the present invention, the content of the polymerizable compound (B) is not particularly limited, but is the total of the allylsilane compound (A), the polymerizable compound (B), and the polymerization initiator (C). Preferably it is 40-99 mass parts, More preferably, it is 50-95 mass parts from 100 mass parts since sclerosis | hardenability is favorable. When the content of the polymerizable compound (B) is less than 40 parts by mass, the curability is inferior, and when it is greater than 99 parts by mass, the adhesion is inferior.
For example, when forming a cured film having a thickness of 1 to 3 μm, the content of the polymerizable compound (B) is 100 masses in total of the allylsilane compound (A), the polymerizable compound (B), and the polymerization initiator (C). Preferably, it is 40-99 mass parts with respect to a part, More preferably, it is 50-95 mass parts.
<重合開始剤(C)>
本発明の硬化性組成物に用いられる重合開始剤(C)としては、従来既知のラジカル重合開始剤及びカチオン重合開始剤を用いることが可能である。
<Polymerization initiator (C)>
As the polymerization initiator (C) used in the curable composition of the present invention, conventionally known radical polymerization initiators and cationic polymerization initiators can be used.
・ラジカル重合開始剤について
上記ラジカル重合開始剤とは、光ラジカル重合開始剤と熱ラジカル重合開始剤である。反応性が高いことから光ラジカル重合開始剤がより好ましい。
-About radical polymerization initiator The said radical polymerization initiator is a radical photopolymerization initiator and a thermal radical polymerization initiator. A radical photopolymerization initiator is more preferred because of its high reactivity.
上記光ラジカル重合開始剤としては、光照射によりラジカルを発生するものであれば特に制限されず従来既知の化合物を用いることが可能であり、例えば、アセトフェノン系化合物、ベンジル系化合物、ベンゾフェノン系化合物、チオキサントン系化合物及びオキシムエステル系化合物等を好ましいものとして例示することができる。 The photo radical polymerization initiator is not particularly limited as long as it generates radicals by light irradiation, and conventionally known compounds can be used. For example, acetophenone compounds, benzyl compounds, benzophenone compounds, Preferred examples include thioxanthone compounds and oxime ester compounds.
上記アセトフェノン系化合物としては例えば、ジエトキシアセトフェノン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、4’−イソプロピル−2−ヒドロキシ−2−メチルプロピオフェノン、2−ヒドロキシメチル−2−メチルプロピオフェノン、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン、p−ジメチルアミノアセトフェノン、p−ターシャリブチルジクロロアセトフェノン、p−ターシャリブチルトリクロロアセトフェノン、p−アジドベンザルアセトフェノン、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパノン−1、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾイン−n−ブチルエーテル、ベンゾインイソブチルエーテル及び1−[4−(2−ヒドロキシエトキシ)−フェニル]−2−ヒドロキシ−2−メチル−1−プロパン−1−オン等が挙げられる。 Examples of the acetophenone compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl- 2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, p-dimethylaminoacetophenone, p-tertiarybutyldichloroacetophenone, p-tertiarybutyltrichloroacetophenone, p-azidoben Salacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) ) -Butanone-1, ben In, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether and 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propane -1-one etc. are mentioned.
上記ベンジル系化合物としては、ベンジル等が挙げられる。 Examples of the benzyl compound include benzyl.
上記ベンゾフェノン系化合物としては、例えば、ベンゾフェノン、o−ベンゾイル安息香酸メチル、ミヒラーケトン、4,4’−ビスジエチルアミノベンゾフェノン、4,4’−ジクロロベンゾフェノン及び4−ベンゾイル−4’−メチルジフェニルスルフィド等が挙げられる。 Examples of the benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone and 4-benzoyl-4′-methyldiphenyl sulfide. It is done.
上記チオキサントン系化合物としては、チオキサントン、2−メチルチオキサントン、2−エチルチオキサントン、2−クロロチオキサントン、2−イソプロピルチオキサントン、2,4−ジエチルチオキサントン等が挙げられる。 Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
上記オキシム系化合物としては、感度及び耐熱性が良好なことから特に、下記一般式(III)で表される化合物が、本発明の硬化性組成物に対して好ましい。 As the oxime compound, a compound represented by the following general formula (III) is particularly preferable for the curable composition of the present invention because of its good sensitivity and heat resistance.
R42及びR43は、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R44、OR45、SR46、NR47R48、COR49、SOR50、SO2R51又はCONR52R53を表し、R40及びR41は、互いに結合して環を形成していてもよく、
R44、R45、R46、R47、R48、R49、R50、R51、R52及びR53は、それぞれ独立に、炭素原子数1〜20のアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアリールアルキル基又は炭素原子数2〜20の複素環含有基を表し、
X1は、酸素原子、硫黄原子、セレン原子、CR54R55、CO、NR56又はPR57を表し、
X2は、単結合又はCOを表し、
R54、R55、R56及びR57は、それぞれ独立に、水素原子、炭素原子数1〜20のアルキル基、炭素原子数6〜20のアリール基又は炭素原子数7〜20のアリールアルキル基を表し、該アルキル基又はアリールアルキル基中のメチレン基は、ハロゲン原子、ニトロ基、シアン基、水酸基、カルボキシル基又は複素環基で置換されていてもよく、−O−で中断されていてもよく、
R54、R55、R56及びR57は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成していてもよい。
cは、0〜5の数を表し、
dは、0〜4の数を表す。)
R 42 and R 43 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, R 44 , OR 45 , SR 46 , NR 47 R 48 , COR 49 , SOR 50 , SO 2. R 51 or CONR 52 R 53 , R 40 and R 41 may be bonded to each other to form a ring;
R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 and R 53 are each independently an alkyl group having 1 to 20 carbon atoms, or 6 to 6 carbon atoms. 20 represents an aryl group, an arylalkyl group having 7 to 20 carbon atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms,
X 1 represents an oxygen atom, a sulfur atom, a selenium atom, CR 54 R 55 , CO, NR 56 or PR 57 ,
X 2 represents a single bond or CO,
R 54 , R 55 , R 56 and R 57 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms. The methylene group in the alkyl group or arylalkyl group may be substituted with a halogen atom, a nitro group, a cyan group, a hydroxyl group, a carboxyl group or a heterocyclic group, or may be interrupted with -O- Often,
R 54 , R 55 , R 56 and R 57 may each independently form a ring together with any adjacent benzene ring.
c represents a number from 0 to 5;
d represents the number of 0-4. )
上記一般式(III)中のR40、R41、R44、R45、R46、R47、R48、R49、R50、R51、R52、R53、R54、R55、R56及びR57で表される炭素原子数1〜20のアルキル基又は炭素原子数6〜20のアリール基としては、上記一般式(I)中のR1の説明で例示したものが挙げられ、
R40、R41、R44、R45、R46、R47、R48、R49、R50、R51、R52、R53、R54、R55、R56及びR57で表される炭素原子数7〜20のアリールアルキル基又は炭素原子数2〜20の複素環基としては、R11〜R39で例示したものが挙げられる。
In the general formula (III), R 40 , R 41 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R 54 , R 55 , Examples of the alkyl group having 1 to 20 carbon atoms or the aryl group having 6 to 20 carbon atoms represented by R 56 and R 57 include those exemplified in the description of R 1 in the general formula (I). ,
R 40, is represented by R 41, R 44, R 45 , R 46, R 47, R 48, R 49, R 50, R 51, R 52, R 53, R 54, R 55, R 56 and R 57 Examples of the arylalkyl group having 7 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms include those exemplified for R 11 to R 39 .
その他のラジカル重合開始剤としては、2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキサイド等のホスフィンオキサイド系化合物及びビス(シクロペンタジエニル)−ビス[2,6−ジフルオロ−3−(ピル−1−イル)]チタニウム等のチタノセン系化合物等が挙げられる。 Other radical polymerization initiators include phosphine oxide compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and bis (cyclopentadienyl) -bis [2,6-difluoro-3- (pyr-1). -Yl)] Titanocene compounds such as titanium.
市販のラジカル開始剤としては、アデカオプトマーN−1414、N−1717、N−1919、アデカアークルズNCI−831、NCI−930(ADEKA社製)、IRGACURE184、IRGACURE369、IRGACURE651、IRGACURE907、IRGACURE OXE 01、IRGACURE OXE 02、IRGACURE784(BASF社製)、TR−PBG−304、TR−PBG−305、TR−PBG−309及びTR−PBG−314(Tronly社製)等が挙げられる。 Commercially available radical initiators include Adekaoptomer N-1414, N-1717, N-1919, Adeka Arcles NCI-831, NCI-930 (manufactured by ADEKA), IRGACURE 184, IRGACURE 369, IRGACURE 651, IRGACURE 907, IRGACURE OX 01 IRGACURE OXE 02, IRGACURE 784 (manufactured by BASF), TR-PBG-304, TR-PBG-305, TR-PBG-309 and TR-PBG-314 (manufactured by Troly).
上記熱ラジカル重合開始剤としては、加熱によりラジカルを発生するものであれば特に制限されず従来既知の化合物を用いることが可能であり、例えば、アゾ系化合物、過酸化物及び過硫酸塩等を好ましいものとして例示することができる。 The thermal radical polymerization initiator is not particularly limited as long as it generates radicals by heating, and conventionally known compounds can be used. For example, azo compounds, peroxides, persulfates and the like can be used. It can be illustrated as preferable.
上記アゾ系化合物としては、2,2′−アゾビスイソブチロニトリル、2,2′−アゾビス(メチルイソブチレ−ト)、2,2’−アゾビス−2,4−ジメチルバレロニトリル、1,1’−アゾビス(1−アセトキシ−1−フェニルエタン)等が挙げられる。 Examples of the azo compound include 2,2'-azobisisobutyronitrile, 2,2'-azobis (methylisobutyrate), 2,2'-azobis-2,4-dimethylvaleronitrile, 1,1 ' -Azobis (1-acetoxy-1-phenylethane) and the like.
過酸化物としては、ベンゾイルパーオキサイド、ジ−t−ブチルベンゾイルパーオキサイド、t−ブチルパーオキシピバレート及びジ(4−t−ブチルシクロヘキシル)パーオキシジカーボネート等が挙げられる。 Examples of the peroxide include benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butyl peroxypivalate, and di (4-t-butylcyclohexyl) peroxydicarbonate.
上記過硫酸塩としては、過硫酸アンモニウム、過硫酸ナトリウム及び過硫酸カリウム等の過硫酸塩等が挙げられる。 Examples of the persulfate include persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate.
・カチオン開始剤について
上記カチオン開始剤とは、光カチオン開始剤と熱カチオン開始剤を示す。
-About a cation initiator The said cation initiator shows a photocation initiator and a thermal cation initiator.
上記光カチオン開始剤は、光照射によりカチオン重合を開始させる物質を放出させることが可能な化合物であれば特に制限されず、既存の化合物を用いることが可能であり、好ましくは、エネルギー線の照射によってルイス酸を放出するオニウム塩である複塩、又はその誘導体である。かかる化合物の代表的なものとしては、下記一般式、
[A]r+[B]r-
で表される陽イオンと陰イオンの塩を挙げることができる。
The photocationic initiator is not particularly limited as long as it is a compound that can release a substance that initiates cationic polymerization by light irradiation, and an existing compound can be used, preferably irradiation with energy rays. Is a double salt that is an onium salt that releases a Lewis acid, or a derivative thereof. Representative examples of such compounds include the following general formula:
[A] r + [B] r-
And cation and anion salts represented by the formula:
上記陽イオン[A]r+はオニウムであることが好ましく、その構造は、例えば、下記一般式、
[(R58)eQ]r+
で表すことができる。
The cation [A] r + is preferably onium, and the structure thereof is, for example, the following general formula:
[(R 58 ) e Q] r +
Can be expressed as
更にここで、R58は炭素原子数が1〜60であり、炭素原子以外の原子をいくつ含んでいてもよい有機の基である。eは1〜5のいずれかの整数である。e個のR58は各々独立で、同一でも異なっていてもよい。また、R58の少なくとも1つは、芳香環を有する上記の如き有機の基であることが好ましい。例えば、アルキル基、アルコキシ基、ヒドロキシ基、ヒドロキシアルコキシ基、ハロゲン原子、ベンジル基、チオフェノキシ基、4−ベンゾイルフェニルチオ基、2−クロロ−4−ベンゾイルフェニルチオ基等で置換されていてもよいフェニル基が挙げられる。QはS,N,Se,Te,P,As,Sb,Bi,O,I,Br,Cl,F,N=Nからなる群から選ばれる原子或いは原子団である。また、陽イオン[A]r+中のQの原子価をqとしたとき、r=e−qなる関係が成り立つことが必要である(但し、N=Nは原子価0として扱う)。 Further, R 58 is an organic group having 1 to 60 carbon atoms and any number of atoms other than carbon atoms. e is an integer of 1 to 5. The e R 58 s are independent and may be the same or different. Further, at least one of R 58 is preferably an organic group as described above having an aromatic ring. For example, it may be substituted with an alkyl group, alkoxy group, hydroxy group, hydroxyalkoxy group, halogen atom, benzyl group, thiophenoxy group, 4-benzoylphenylthio group, 2-chloro-4-benzoylphenylthio group, etc. A phenyl group is mentioned. Q is an atom or atomic group selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, F, and N = N. Further, when the valence of Q in the cation [A] r + is q, the relationship r = e−q needs to be satisfied (however, N = N is treated as a valence of 0).
また、陰イオン[B]r-は、ハロゲン化物錯体であることが好ましく、その構造は、例えば、下記一般式、[LXf]r-で表すことができる。 The anion [B] r− is preferably a halide complex, and the structure thereof can be represented by, for example, the following general formula, [LX f ] r− .
更にここで、Lはハロゲン化物錯体の中心原子である金属又は半金属(Metalloid)であり、B,P,As,Sb,Fe,Sn,Bi,Al,Ca,In,Ti,Zn,Sc,V,Cr,Mn及びCo等である。Xはハロゲン原子、又は、ハロゲン原子やアルコキシ基等で置換されていてもよいフェニル基である。fは3〜7なる整数である。また、陰イオン[B]r-中のLの原子価をpとしたとき、r=f−pなる関係が成り立つことが必要である。 Further, here, L is a metal or metalloid which is a central atom of a halide complex, and B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, Co and the like. X is a halogen atom or a phenyl group which may be substituted with a halogen atom, an alkoxy group or the like. f is an integer of 3-7. Further, when the valence of L in the anion [B] r− is p, it is necessary that the relationship r = fp is established.
上記一般式の陰イオン[LXf]r-の具体例としては、テトラキス(ペンタフルオロフェニル)ボレート、テトラ(3,5−ジフルオロ−4−メトキシフェニル)ボレート、テトラフルオロボレート(BF4)−、ヘキサフルオロフォスフェート(PF6)-、ヘキサフルオロアンチモネート(SbF6)-、ヘキサフルオロアルセネート(AsF6)-及びヘキサクロロアンチモネート(SbCl6)-等を挙げることができる。 Specific examples of the anion [LX f ] r− of the above general formula include tetrakis (pentafluorophenyl) borate, tetra (3,5-difluoro-4-methoxyphenyl) borate, tetrafluoroborate (BF 4 ) —, Examples include hexafluorophosphate (PF 6 ) − , hexafluoroantimonate (SbF 6 ) − , hexafluoroarsenate (AsF 6 ) −, and hexachloroantimonate (SbCl 6 ) − .
また、陰イオン[B]r-は、下記一般式、
[LXf-1(OH)]r-
で表される構造のものも好ましく用いることができる。L,X,fは上記と同様である。また、その他用いることのできる陰イオンとしては、過塩素酸イオン(ClO4)−、トリフルオロメチル亜硫酸イオン(CF3SO3)-、フルオロスルホン酸イオン(FSO3)-、トルエンスルホン酸陰イオン、トリニトロベンゼンスルホン酸陰イオン、カンファースルフォネート、ノナフロロブタンスルフォネート、ヘキサデカフロロオクタンスルフォネート、テトラアリールボレート及びテトラキス(ペンタフルオロフェニル)ボレート等を挙げることができる。
Further, the anion [B] r− is represented by the following general formula:
[LX f-1 (OH)] r-
The thing of the structure represented by can also be used preferably. L, X, and f are the same as described above. Other anions that can be used include perchlorate ion (ClO 4 ) −, trifluoromethyl sulfite ion (CF 3 SO 3 ) − , fluorosulfonate ion (FSO 3 ) − , and toluenesulfonate anion. , Trinitrobenzenesulfonate anion, camphor sulfonate, nonafluorobutane sulfonate, hexadecafluorooctane sulfonate, tetraarylborate and tetrakis (pentafluorophenyl) borate.
本発明では、このようなオニウム塩の中でも、下記の(ホ)〜(ト)の芳香族オニウム塩を使用することが特に有効であり、好ましい。これらの中から、その1種を単独で、又は2種以上を混合して使用することができる。 In the present invention, among these onium salts, it is particularly effective and preferable to use the following (e) to (g) aromatic onium salts. Among these, one of them can be used alone, or two or more can be mixed and used.
(ホ)フェニルジアゾニウムヘキサフルオロホスフェート、4−メトキシフェニルジアゾニウムヘキサフルオロアンチモネート及び4−メチルフェニルジアゾニウムヘキサフルオロホスフェート等のアリールジアゾニウム塩。 (E) aryldiazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate and 4-methylphenyldiazonium hexafluorophosphate;
(へ)ジフェニルヨードニウムヘキサフルオロアンチモネート、ジ(4−メチルフェニル)ヨードニウムヘキサフルオロホスフェート、ジ(4−tert−ブチルフェニル)ヨードニウムヘキサフルオロホスフェート及びトリルクミルヨードニウムテトラキス(ペンタフルオロフェニル)ボレート等のジアリールヨードニウム塩。 (F) Diaryls such as diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, and tricumyliodonium tetrakis (pentafluorophenyl) borate Iodonium salt.
(ト)下記群I又は群IIで表されるスルホニウムカチオンとヘキサフルオロアンチモンイオン、テトラキス(ペンタフルオロフェニル)ボレートイオン等のスルホニウム塩 (G) Sulfonium salts such as sulfonium cations represented by the following group I or group II, hexafluoroantimony ions, tetrakis (pentafluorophenyl) borate ions, etc.
また、その他好ましいものとしては、(η5−2,4−シクロペンタジエン−1−イル)〔(1,2,3,4,5,6−η)−(1−メチルエチル)ベンゼン〕−アイアン−ヘキサフルオロホスフェート等の鉄−アレーン錯体;トリス(アセチルアセトナト)アルミニウム、トリス(エチルアセトナトアセタト)アルミニウム、トリス(サリチルアルデヒダト)アルミニウム等のアルミニウム錯体;トリフェニルシラノール等のシラノール類との混合物:等も挙げることができる。 Other preferable examples include (η5-2,4-cyclopentadien-1-yl) [(1,2,3,4,5,6-η)-(1-methylethyl) benzene] -iron- Iron-arene complexes such as hexafluorophosphate; aluminum complexes such as tris (acetylacetonato) aluminum, tris (ethylacetonatoacetato) aluminum, tris (salicylaldehyde) aluminum; mixtures with silanols such as triphenylsilanol : Etc. can also be mentioned.
上記光カチオン開始剤としては、市販品を用いることもでき、例えば、IRUGACURE261(BASF社製)、アデカオプトマーSP−150、SP−151、SP−152、SP−170、SP−171、SP−172(ADEKA社製)、UVE−1014(ゼネラルエレクトロニクス社製)、CD−1012(サートマー社製)、CI−2064、CI−2481(日本曹達社製)、Uvacure1590 、1591(ダイセルUCB)、CYRACURE UVI−6990(ユニオンカーバイド社製)、BBI-103、MPI-103、TPS-103、MDS-103、DTS-103、NAT-103及びNDS-103(ミドリ化学社製)等が挙げられる。 A commercial item can also be used as said photocationic initiator, for example, IRUGACURE261 (made by BASF), Adeka optomer SP-150, SP-151, SP-152, SP-170, SP-171, SP- 172 (manufactured by ADEKA), UVE-1014 (manufactured by General Electronics), CD-1012 (manufactured by Sartomer), CI-2064, CI-2481 (manufactured by Nippon Soda), Uvacure 1590, 1591 (Daicel UCB), CYRACURE UVI -6990 (manufactured by Union Carbide), BBI-103, MPI-103, TPS-103, MDS-103, DTS-103, NAT-103 and NDS-103 (manufactured by Midori Chemical).
これらの中でも、実用面と光感度の観点から、芳香族ヨードニウム塩、芳香族スルホニウム塩、鉄−アレーン錯体を用いることが好ましい。 Among these, from the viewpoint of practical use and photosensitivity, it is preferable to use an aromatic iodonium salt, an aromatic sulfonium salt, or an iron-arene complex.
上記熱カチオン開始剤とは、加熱によりカチオン種又はルイス酸を発生する化合物であれば特に制限されず、既存の化合物を用いることが可能である。かかる化合物の代表的なものとしては、スルホニウム塩、チオフェニウム塩、チオラニウム塩、ベンジルアンモニウム、ピリジニウム塩及びヒドラジニウム塩等の塩;ジエチレントリアミン、トリエチレントリアミン及びテトラエチレンペンタミン等のポリアルキルポリアミン類;1,2−ジアミノシクロヘキサン、1,4−ジアミノ−3,6−ジエチルシクロヘキサン及びイソホロンジアミン等の脂環式ポリアミン類;m−キシリレンジアミン、ジアミノジフェニルメタン及びジアミノジフェニルスルホン等の芳香族ポリアミン類;前記ポリアミン類と、フェニルグリシジルエーテル、ブチルグリシジルエーテル、ビスフェノールA−ジグリシジルエーテル及びビスフェノールF−ジグリシジルエーテル等のグリシジルエーテル類又はカルボン酸のグリシジルエステル類等の各種エポキシ樹脂とを常法によって反応させることによって製造されるポリエポキシ付加変性物;前記有機ポリアミン類と、フタル酸、イソフタル酸及びダイマー酸等のカルボン酸類とを常法によって反応させることによって製造されるアミド化変性物;前記ポリアミン類とホルムアルデヒド等のアルデヒド類;フェノール、クレゾール、キシレノール、第三ブチルフェノール及びレゾルシン等の核に少なくとも一個のアルデヒド化反応性場所を有するフェノール類とを常法によって反応させることによって製造されるマンニッヒ化変性物;多価カルボン酸(シュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、ドデカン二酸、2−メチルコハク酸、2−メチルアジピン酸、3−メチルアジピン酸、3−メチルペンタン二酸、2−メチルオクタン二酸、3,8−ジメチルデカン二酸、3,7−ジメチルデカン二酸、水添ダイマー酸及びダイマー酸等の脂肪族ジカルボン酸類;フタル酸、テレフタル酸、イソフタル酸及びナフタレンジカルボン酸等の芳香族ジカルボン酸類;シクロヘキサンジカルボン酸等の脂環式ジカルボン酸類;トリメリット酸、トリメシン酸及びひまし油脂肪酸等の三量体等のトリカルボン酸類;ピロメリット酸等のテトラカルボン酸類等)の酸無水物;ジシアンジアミド、イミダゾール類、カルボン酸エステル、スルホン酸エステル及びアミンイミド等を挙げることができる。
上記熱カチオン開始剤としては、市販品を用いることもでき、例えば、アデカオプトン CP−77、アデカオプトンCP−66(ADEKA社製)、CI−2639、CI−2624(日本曹達社製)、サンエイド SI−60L、サンエイドSI−80L、サンエイド SI−100L(三新化学工業社製)等が挙げられる。
The thermal cation initiator is not particularly limited as long as it is a compound that generates a cationic species or a Lewis acid by heating, and an existing compound can be used. Representative examples of such compounds include salts such as sulfonium salts, thiophenium salts, thioranium salts, benzylammonium, pyridinium salts, and hydrazinium salts; polyalkylpolyamines such as diethylenetriamine, triethylenetriamine, and tetraethylenepentamine; Cycloaliphatic polyamines such as 2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane and isophoronediamine; aromatic polyamines such as m-xylylenediamine, diaminodiphenylmethane and diaminodiphenylsulfone; And glycidyl ethers such as phenyl glycidyl ether, butyl glycidyl ether, bisphenol A-diglycidyl ether and bisphenol F-diglycidyl ether, or cal A polyepoxy addition-modified product produced by reacting various epoxy resins such as glycidyl esters of acid by a conventional method; the organic polyamines and carboxylic acids such as phthalic acid, isophthalic acid and dimer acid are usually used. Amidation modified products produced by reacting by the method; aldehydes such as polyamines and formaldehyde; phenols having at least one aldehyde-reactive site in the nucleus such as phenol, cresol, xylenol, tert-butylphenol and resorcin Mannich-modified product produced by reacting with benzoic acid by a conventional method; polycarboxylic acid (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, Dodecanedioic acid, 2-methyl succinate Acid, 2-methyladipic acid, 3-methyladipic acid, 3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecanedioic acid, hydrogenated dimer acid And aliphatic dicarboxylic acids such as dimer acid; aromatic dicarboxylic acids such as phthalic acid, terephthalic acid, isophthalic acid and naphthalenedicarboxylic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; trimellitic acid, trimesic acid and castor oil fatty acid, etc. And tricarboxylic acids such as trimer; tetracarboxylic acids such as pyromellitic acid) acid anhydrides; dicyandiamide, imidazoles, carboxylic acid esters, sulfonic acid esters, and amine imides.
A commercial item can also be used as said thermal cation initiator, for example, Adeka Opton CP-77, Adeka Opton CP-66 (made by ADEKA), CI-2639, CI-2624 (made by Nippon Soda Co., Ltd.), Sun-Aid SI- 60L, Sun-Aid SI-80L, Sun-Aid SI-100L (manufactured by Sanshin Chemical Industry Co., Ltd.) and the like.
上記重合開始剤(C)は、これまでに例示した一種又は二種以上を混合して用いることができる。 The said polymerization initiator (C) can mix and use 1 type, or 2 or more types illustrated so far.
本発明の硬化性組成物において、上記重合開始剤(C)の含有量は、特に限定されるものではないが、アリルシラン化合物(A)、重合性化合物(B)及び重合開始剤(C)の合計100質量部に対して、硬化性が良好なことから好ましくは、0.5〜30質量部、より好ましくは、1〜20質量部である。重合性化合物(B)の含有量が、0.5質量部より小さいと硬化性が劣り、30質量部より大きいと、硬化性組成物中に重合開始剤(C)が析出する場合がある。例えば膜厚1〜3μmの硬化膜を形成する場合には、重合開始剤(C)の含有量は、アリルシラン化合物(A)、重合性化合物(B)及び重合開始剤(C)の合計100質量部に対して、好ましくは、0.5〜30質量部、より好ましくは、1〜20質量部である。 In the curable composition of the present invention, the content of the polymerization initiator (C) is not particularly limited, but the allylsilane compound (A), the polymerizable compound (B), and the polymerization initiator (C). Preferably it is 0.5-30 mass parts, More preferably, it is 1-20 mass parts from sclerosis | hardenability with respect to a total of 100 mass parts. When the content of the polymerizable compound (B) is less than 0.5 parts by mass, the curability is inferior, and when it is greater than 30 parts by mass, the polymerization initiator (C) may be precipitated in the curable composition. For example, when forming a cured film having a thickness of 1 to 3 μm, the content of the polymerization initiator (C) is 100 masses in total of the allylsilane compound (A), the polymerizable compound (B), and the polymerization initiator (C). Preferably, it is 0.5-30 mass parts with respect to a part, More preferably, it is 1-20 mass parts.
<着色剤(D)>
本発明の硬化性組成物には、さらに着色剤(D)を用いることができ、該着色剤(D)としては、無機色材又は有機色材を用いることができ、これらは単独で又は2種以上を混合して用いることができる。
上記無機色材又は有機色材としては、例えば、ニトロソ化合物、ニトロ化合物、アゾ化合物、ジアゾ化合物、キサンテン化合物、キノリン化合物、アントラキノン化合物、クマリン化合物、フタロシアニン化合物、イソインドリノン化合物、イソインドリン化合物、キナクリドン化合物、アンタンスロン化合物、ペリノン化合物、ペリレン化合物、ジケトピロロピロール化合物、チオインジゴ化合物、ジオキサジン化合物、トリフェニルメタン化合物、キノフタロン化合物、ナフタレンテトラカルボン酸、アゾ染料、シアニン染料の金属錯体化合物、レーキ顔料、ファーネス法、チャンネル法又はサーマル法によって得られるカーボンブラック、或いはアセチレンブラック、ケッチェンブラック又はランプブラック等のカーボンブラック、上記カーボンブラックをエポキシ樹脂で調整又は被覆したもの、上記カーボンブラックを予め溶剤中で樹脂に分散処理し、20〜200mg/gの樹脂を吸着させたもの、上記カーボンブラックを酸性又はアルカリ性表面処理したもの、平均粒径が8nm以上でDBP吸油量が90ml/100g以下のカーボンブラック、950℃における揮発分中のCO及びCO2から算出した全酸素量が、表面積100m2当たり9mg以上であるカーボンブラック、黒鉛、黒鉛化カーボンブラック、活性炭、炭素繊維、カーボンナノチューブ、カーボンマイクロコイル、カーボンナノホーン、カーボンエアロゲル、フラーレン、アニリンブラック、ピグメントブラック7、チタンブラック、酸化クロム緑、ミロリブルー、コバルト緑、コバルト青、マンガン系、フェロシアン化物、リン酸塩群青、紺青、ウルトラマリン、セルリアンブルー、ピリジアン、エメラルドグリーン、硫酸鉛、黄色鉛、亜鉛黄、べんがら(赤色酸化鉄(III))、カドミウム赤、合成鉄黒及びアンバー等の有機又は無機顔料を用いることができる。
<Colorant (D)>
In the curable composition of the present invention, a colorant (D) can be further used. As the colorant (D), an inorganic color material or an organic color material can be used, and these can be used alone or in combination. A mixture of seeds or more can be used.
Examples of the inorganic color material or organic color material include nitroso compounds, nitro compounds, azo compounds, diazo compounds, xanthene compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, isoindoline compounds, and quinacridones. Compound, anthanthrone compound, perinone compound, perylene compound, diketopyrrolopyrrole compound, thioindigo compound, dioxazine compound, triphenylmethane compound, quinophthalone compound, naphthalenetetracarboxylic acid, azo dye, metal complex compound of cyanine dye, lake pigment, furnace Carbon black obtained by the method, channel method or thermal method, or carbon black such as acetylene black, ketjen black or lamp black, Carbon black adjusted or coated with epoxy resin, carbon black previously dispersed in resin in a solvent, 20 to 200 mg / g of resin adsorbed, carbon black treated with acidic or alkaline surface Carbon black having an average particle size of 8 nm or more and a DBP oil absorption of 90 ml / 100 g or less, carbon black having a total oxygen amount calculated from CO and CO2 in volatiles at 950 ° C. of 9 mg or more per 100 m2 of surface area, graphite, Graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon aerogel, fullerene, aniline black, pigment black 7, titanium black, chromium oxide green, miloli blue, cobalt green, cobalt blue, manganese Series, ferrocyanide, phosphate ultramarine, bitumen, ultramarine, cerulean blue, pyridian, emerald green, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, synthetic iron black and Organic or inorganic pigments such as amber can be used.
上記無機色材又は有機色材としては、市販の顔料を用いることもでき、例えば、ピグメントレッド1、2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、254、228、240及び254等;ピグメントオレンジ13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65及び71等;ピグメントイエロー1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180及び185等;ピグメントグリ−ン7、10、36及び58等;ピグメントブルー15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62及び64等;ピグメントバイオレット1、19、23、27、29、30、32、37、40及び50等が挙げられる。 As the inorganic color material or organic color material, commercially available pigments can also be used. For example, Pigment Red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 254, 228, 240, 254, etc .; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59 , 60, 61, 62, 64, 65 and 71, etc .; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 8 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152 153, 154, 166, 168, 175, 180 and 185, etc .; Pigment Green 7, 10, 36 and 58 etc .; Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15 : 5, 15: 6, 22, 24, 56, 60, 61, 62 and 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40 and 50, and the like.
上記無機色材又は有機色材としては、公知の染料を用いることも可能である。公知の染料としては例えば、アゾ染料、アントラキノン染料、インジゴイド染料、トリアリールメタン染料、キサンテン染料、アリザリン染料、アクリジン染料スチルベン染料、チアゾール染料、ナフトール染料、キノリン染料、ニトロ染料、インダミン染料、オキサジン染料、フタロシアニン染料及びシアニン染料等の染料等が挙げられる。 As the inorganic color material or organic color material, known dyes can be used. Known dyes include, for example, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, And dyes such as phthalocyanine dyes and cyanine dyes.
本発明の硬化性組成物において、上記着色剤(D)の含有量は、上記重合性化合物(B)100質量部に対して、好ましくは0〜350質量部、より好ましくは0〜250質量部である。350質量部を超えると、着色剤が凝集しやすくなり保存安定性が悪くなる。
例えば膜厚1〜3μmの硬化膜を形成する場合には、着色剤(D)の含有量は、ラジカル重合性を有する重合性化合物100質量部に対して、好ましくは、0〜350質量部、より好ましくは、0〜250質量部である。
In the curable composition of the present invention, the content of the colorant (D) is preferably 0 to 350 parts by mass, more preferably 0 to 250 parts by mass with respect to 100 parts by mass of the polymerizable compound (B). It is. When it exceeds 350 parts by mass, the colorant tends to aggregate and storage stability is deteriorated.
For example, when forming a cured film having a thickness of 1 to 3 μm, the content of the colorant (D) is preferably 0 to 350 parts by mass with respect to 100 parts by mass of the polymerizable compound having radical polymerizability. More preferably, it is 0-250 mass parts.
本発明の硬化性組成物には、更に溶剤を加えることができる。該溶剤としては、通常、必要に応じて上記の各成分(アリルシラン化合物(A)、重合性化合物(B)、重合開始剤(C)及び着色剤(D)等)を溶解又は分散しえる溶剤、例えば、メチルエチルケトン、メチルアミルケトン、ジエチルケトン、アセトン、メチルイソプロピルケトン、メチルイソブチルケトン、シクロヘキサノン及び2−ヘプタノン等のケトン類;エチルエーテル、ジオキサン、テトラヒドロフラン、1,2−ジメトキシエタン、1,2−ジエトキシエタン及びジプロピレングリコールジメチルエーテル等のエーテル系溶剤;酢酸メチル、酢酸エチル、酢酸−n−プロピル、酢酸イソプロピル、酢酸n−ブチル、酢酸シクロヘキシル、乳酸エチル、コハク酸ジメチル及びテキサノール等のエステル系溶剤;エチレングリコールモノメチルエーテル及びエチレングリコールモノエチルエーテル等のセロソルブ系溶剤;メタノール、エタノール、イソ−又はn−プロパノール、イソ−又はn−ブタノール及びアミルアルコール等のアルコール系溶剤;エチレングリコールモノメチルアセテート、エチレングリコールモノエチルアセテート、プロピレングリコール−1−モノメチルエーテル−2−アセテート(PGMEA)、ジプロピレングリコールモノメチルエーテルアセテート、3−メトキシブチルアセテート及びエトキシエチルプロピオネート等のエーテルエステル系溶剤;ベンゼン、トルエン及びキシレン等のBTX系溶剤;ヘキサン、ヘプタン、オクタン及びシクロヘキサン等の脂肪族炭化水素系溶剤;テレピン油、D−リモネン及びピネン等のテルペン系炭化水素油;ミネラルスピリット、スワゾール#310(コスモ松山石油社製)及びソルベッソ#100(エクソン化学社製)等のパラフィン系溶剤;四塩化炭素、クロロホルム、トリクロロエチレン、塩化メチレン及び1,2−ジクロロエタン等のハロゲン化脂肪族炭化水素系溶剤;クロロベンゼン等のハロゲン化芳香族炭化水素系溶剤;カルビトール系溶剤、アニリン、トリエチルアミン、ピリジン、酢酸、アセトニトリル、二硫化炭素、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチルピロリドン、ジメチルスルホキシド及び水等が挙げられ、これらの溶剤は1種又は2種以上の混合溶剤として使用することができる。これらの中でもケトン類及びエーテルエステル系溶剤等、特にプロピレングリコール−1−モノメチルエーテル−2−アセテート(PGMEA)及びシクロヘキサノン等が、着色組成物においてレジストと重合開始剤の相溶性がよいので好ましい。 A solvent can be further added to the curable composition of the present invention. As the solvent, usually, a solvent capable of dissolving or dispersing each of the above components (allyl silane compound (A), polymerizable compound (B), polymerization initiator (C), colorant (D), etc.) as necessary. Ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone and 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2- Ether solvents such as diethoxyethane and dipropylene glycol dimethyl ether; ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate and texanol Ethylene glycol Cellosolve solvents such as monomethyl ether and ethylene glycol monoethyl ether; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol and amyl alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate , Ether ester solvents such as propylene glycol-1-monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate and ethoxyethyl propionate; BTX systems such as benzene, toluene and xylene Solvent: Aliphatic hydrocarbon solvents such as hexane, heptane, octane and cyclohexane; Terpene charcoal such as turpentine oil, D-limonene and pinene Hydrogen oil; paraffinic solvents such as mineral spirits, swazol # 310 (manufactured by Cosmo Matsuyama Petroleum) and Solvesso # 100 (manufactured by Exxon Chemical); carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, 1,2-dichloroethane, etc. Halogenated aliphatic hydrocarbon solvents; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide, N, N -Dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, water, etc. are mentioned, These solvents can be used as 1 type, or 2 or more types of mixed solvents. Among these, ketones and ether ester solvents, etc., particularly propylene glycol-1-monomethyl ether-2-acetate (PGMEA) and cyclohexanone are preferable because the compatibility of the resist and the polymerization initiator in the colored composition is good.
本発明の硬化性組成物において、上記溶剤の使用量は、溶剤以外の組成物の濃度が5〜30質量%になることが好ましく、5質量%より小さい場合、膜厚を厚くする事が困難であり所望の波長光を十分に吸収できないため好ましくなく、30質量%を超える場合、組成物の析出による組成物の保存性が低下したり、粘度が向上したりするためハンドリングが低下するため好ましくない。 In the curable composition of the present invention, the amount of the solvent used is preferably such that the concentration of the composition other than the solvent is 5 to 30% by mass, and if it is less than 5% by mass, it is difficult to increase the film thickness. It is not preferable because it cannot sufficiently absorb light of a desired wavelength, and when it exceeds 30% by mass, the storage stability of the composition due to precipitation of the composition is decreased, and the viscosity is improved, so that handling is decreased. Absent.
本発明の硬化性組成物には、更に分散剤を用いることができる。該分散剤としては、着色剤(D)を分散、安定化できるものであれば何でも良く、市販の分散剤、例えばビックケミー社製、BYKシリーズ等を用いることができ、塩基性官能基を有するポリエステル、ポリエーテル、ポリウレタンからなる高分子分散剤、塩基性官能基として窒素原子を有し、窒素原子を有する官能基がアミン、及び/又はその四級塩であり、アミン価が1〜100mgKOH/gのものが好適に用いられる。 A dispersant can be further used in the curable composition of the present invention. As the dispersant, any dispersant can be used as long as it can disperse and stabilize the colorant (D). Commercially available dispersants such as BYK series manufactured by Big Chemie can be used, and polyester having a basic functional group. , A polymer dispersant made of polyether or polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Are preferably used.
本発明の硬化性組成物には、更に無機化合物を含有させることができる。該無機化合物としては、例えば、酸化ニッケル、酸化鉄、酸化イリジウム、酸化チタン、酸化亜鉛、酸化マグネシウム、酸化カルシウム、酸化カリウム、シリカ及びアルミナ等の金属酸化物;層状粘土鉱物、ミロリブルー、炭酸カルシウム、炭酸マグネシウム、コバルト系、マンガン系、ガラス粉末、マイカ、タルク、カオリン、フェロシアン化物、各種金属硫酸塩、硫化物、セレン化物、アルミニウムシリケート、カルシウムシリケート、水酸化アルミニウム、白金、金、銀及び銅等が挙げられ、これらの中でも、酸化チタン、シリカ、層状粘土鉱物、及び銀等が好ましい。本発明の硬化性組成物において、無機化合物の含有量は、上記重合性化合物(B)100質量部に対して、好ましくは0.1〜50質量部、より好ましくは0.5〜20質量部であり、これらの無機化合物は1種又は2種以上を使用することができる。 The curable composition of the present invention may further contain an inorganic compound. Examples of the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver and copper Among these, titanium oxide, silica, layered clay mineral, silver and the like are preferable. In the curable composition of the present invention, the content of the inorganic compound is preferably 0.1 to 50 parts by mass, more preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the polymerizable compound (B). These inorganic compounds can be used alone or in combination of two or more.
本発明の硬化性組成物に無機化合物を含有させることで、感光性ペースト組成物として用いることができる。該感光性ペースト組成物は、プラズマディスプレイパネルの隔壁パターン、誘電体パターン、電極パターン及びブラックマトリックスパターン等の焼成物パターンを形成するために用いられる。
また、これら無機化合物は、例えば、充填剤、反射防止剤、導電剤、安定剤、難燃剤、機械的強度向上剤、特殊波長吸収剤及び撥インク剤等としても好適に用いられる。
By containing an inorganic compound in the curable composition of the present invention, it can be used as a photosensitive paste composition. The photosensitive paste composition is used to form a fired product pattern such as a partition pattern, a dielectric pattern, an electrode pattern, and a black matrix pattern of a plasma display panel.
These inorganic compounds are also suitably used as, for example, fillers, antireflection agents, conductive agents, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, and ink repellent agents.
また、本発明の硬化性組成物には、必要に応じて、p−アニソール、ハイドロキノン、ピロカテコール、t−ブチルカテコール及びフェノチアジン等の熱重合抑制剤;可塑剤;接着促進剤;充填剤;消泡剤;レベリング剤;表面調整剤;酸化防止剤;紫外線吸収剤;分散助剤;凝集防止剤;触媒;効果促進剤;架橋剤;増粘剤等の慣用の添加物を加えることができる。 In addition, the curable composition of the present invention includes, if necessary, a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol and phenothiazine; a plasticizer; an adhesion promoter; a filler; Conventional additives such as a foaming agent, a leveling agent, a surface conditioner, an antioxidant, an ultraviolet absorber, a dispersion aid, a coagulation inhibitor, a catalyst, an effect accelerator, a cross-linking agent, and a thickener can be added.
本発明の硬化性組成物には、更に、連鎖移動剤、増感剤、界面活性剤及びメラミン等を併用することができる。 The curable composition of the present invention may further contain a chain transfer agent, a sensitizer, a surfactant, melamine, and the like.
上記連鎖移動剤、増感剤としては、一般的に硫黄原子含有化合物が用いられる。例えばチオグリコール酸、チオリンゴ酸、チオサリチル酸、2−メルカプトプロピオン酸、3−メルカプトプロピオン酸、3−メルカプト酪酸、N−(2−メルカプトプロピオニル)グリシン、2−メルカプトニコチン酸、3−[N−(2−メルカプトエチル)カルバモイル]プロピオン酸、3−[N−(2−メルカプトエチル)アミノ]プロピオン酸、N−(3−メルカプトプロピオニル)アラニン、2−メルカプトエタンスルホン酸、3−メルカプトプロパンスルホン酸、4−メルカプトブタンスルホン酸、ドデシル(4−メチルチオ)フェニルエーテル、2−メルカプトエタノール、3−メルカプト−1,2−プロパンジオール、1−メルカプト−2−プロパノール、3−メルカプト−2−ブタノール、メルカプトフェノール、2−メルカプトエチルアミン、2−メルカプトイミダゾール、2−メルカプトベンゾイミダゾール、2−メルカプト−3−ピリジノール、2−メルカプトベンゾチアゾール、メルカプト酢酸、トリメチロールプロパントリス(3−メルカプトプロピオネート)及びペンタエリスリトールテトラキス(3−メルカプトプロピオネート)等のメルカプト化合物;該メルカプト化合物を酸化して得られるジスルフィド化合物、ヨード酢酸、ヨードプロピオン酸、2−ヨードエタノール、2−ヨードエタンスルホン酸及び3−ヨードプロパンスルホン酸等のヨード化アルキル化合物;トリメチロールプロパントリス(3−メルカプトイソブチレート)、ブタンジオールビス(3−メルカプトイソブチレート)、ヘキサンジチオール、デカンジチオール、1,4−ジメチルメルカプトベンゼン、ブタンジオールビスチオプロピオネート、ブタンジオールビスチオグリコレート、エチレングリコールビスチオグリコレート、トリメチロールプロパントリスチオグリコレート、ブタンジオールビスチオプロピオネート、トリメチロールプロパントリスチオプロピオネート、トリメチロールプロパントリスチオグリコレート、ペンタエリスリトールテトラキスチオプロピオネート、ペンタエリスリトールテトラキスチオグリコレート、トリスヒドロキシエチルトリスチオプロピオネート、下記化合物No.C1、昭和電工社製カレンズPE1及びNR1等が挙げられる。 As the chain transfer agent and sensitizer, a sulfur atom-containing compound is generally used. For example, thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropionyl) glycine, 2-mercaptonicotinic acid, 3- [N- ( 2-mercaptoethyl) carbamoyl] propionic acid, 3- [N- (2-mercaptoethyl) amino] propionic acid, N- (3-mercaptopropionyl) alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1-mercapto-2-propanol, 3-mercapto-2-butanol, mercaptophenol , 2-me Captoethylamine, 2-mercaptoimidazole, 2-mercaptobenzimidazole, 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropane tris (3-mercaptopropionate) and pentaerythritol tetrakis (3- Mercapto compounds such as mercaptopropionate); iodo such as disulfide compounds obtained by oxidizing the mercapto compound, iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid and 3-iodopropanesulfonic acid Alkyl compound; trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1, -Dimethyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropioate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyltristhiopropionate, the following compound No. C1, Karenz PE1 and NR1 manufactured by Showa Denko KK and the like.
上記界面活性剤としては、パーフルオロアルキルリン酸エステル、パーフルオロアルキルカルボン酸塩等のフッ素界面活性剤、高級脂肪酸アルカリ塩、アルキルスルホン酸塩、アルキル硫酸塩等のアニオン系界面活性剤、高級アミンハロゲン酸塩、第四級アンモニウム塩等のカチオン系界面活性剤、ポリエチレングリコールアルキルエーテル、ポリエチレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、脂肪酸モノグリセリド等の非イオン界面活性剤、両性界面活性剤及びシリコーン系界面活性剤等の界面活性剤を用いることができ、これらは組み合わせて用いてもよい。 Examples of the surfactant include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters, fatty acid monoglycerides, amphoteric surfactants and silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
上記メラミン化合物としては、(ポリ)メチロールメラミン、(ポリ)メチロールグリコールウリル、(ポリ)メチロールベンゾグアナミン及び(ポリ)メチロールウレア等の窒素化合物中の活性メチロール基(CH2OH基)の全部又は一部(少なくとも2つ)がアルキルエーテル化された化合物を挙げることができる。ここで、アルキルエーテルを構成するアルキル基としては、メチル基、エチル基及びブチル基が挙げられ、互いに同一であってもよいし、異なっていてもよい。また、アルキルエーテル化されていないメチロール基は、一分子内で自己縮合していてもよく、二分子間で縮合して、その結果オリゴマー成分が形成されていてもよい。具体的には、ヘキサメトキシメチルメラミン、ヘキサブトキシメチルメラミン、テトラメトキシメチルグリコールウリル及びテトラブトキシメチルグリコールウリル等を用いることができる。これらのなかでも、ヘキサメトキシメチルメラミン及びヘキサブトキシメチルメラミン等のアルキルエーテル化されたメラミンが好ましい。 Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified. Here, examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other. Moreover, the methylol group which is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules, and as a result, an oligomer component may be formed. Specifically, hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril, and the like can be used. Among these, alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
本発明の硬化性組成物において、アリルシラン化合物(A)、重合性化合物(B)、重合開始剤(C)、及び溶剤以外の任意成分の含有量は、その使用目的に応じて適宜選択され特に制限されないが、好ましくは、硬化性組成物の固形分100質量部に対して合計で20質量部以下とする。 In the curable composition of the present invention, the contents of the optional components other than the allylsilane compound (A), the polymerizable compound (B), the polymerization initiator (C), and the solvent are appropriately selected according to the purpose of use. Although not limited, Preferably, it is 20 mass parts or less in total with respect to 100 mass parts of solid content of a curable composition.
本発明の硬化性組成物は、硬化性塗料、ワニス、硬化性接着剤、プリント基板、或いはカラーテレビ、PCモニタ、携帯情報端末及びデジタルカメラ等のカラー表示の液晶表示パネルにおけるカラーフィルタ、CCDイメージセンサのカラーフィルタ、タッチパネル、プラズマ表示パネル用の電極材料、粉末コーティング、印刷インク、印刷版、接着剤、ゲルコート、電子工学用のフォトレジスト、電気メッキレジスト、エッチングレジスト、はんだレジスト、絶縁膜、ブラックマトリックス、種々の表示用途用のカラーフィルタ、プラズマ表示パネル、電気発光表示装置、及びLCDの製造工程において構造を形成するためのレジスト、電気及び電子部品を封入するための組成物、ソルダーレジスト、磁気記録材料、微小機械部品、導波路、光スイッチ、めっき用マスク、エッチングマスク、カラー試験系、ガラス繊維ケーブルコーティング、スクリーン印刷用ステンシル、ステレオリトグラフィによって三次元物体を製造するための材料、ホログラフィ記録用材料、画像記録材料、微細電子回路、脱色材料、画像記録材料のための脱色材料、マイクロカプセルを使用する画像記録材料用の脱色材料、印刷配線板用フォトレジスト材料、UV及び可視レーザー直接画像系用のフォトレジスト材料、プリント回路基板の逐次積層における誘電体層形成に使用するフォトレジスト材料及び保護膜等の各種の用途に使用することができ、その用途に特に制限はない。 The curable composition of the present invention comprises a curable paint, a varnish, a curable adhesive, a printed circuit board, or a color filter, a CCD image in a color display liquid crystal display panel such as a color television, a PC monitor, a personal digital assistant, and a digital camera. Sensor color filter, touch panel, electrode material for plasma display panel, powder coating, printing ink, printing plate, adhesive, gel coat, photo resist for electronics, electroplating resist, etching resist, solder resist, insulating film, black Matrix, color filters for various display applications, plasma display panels, electroluminescent display devices, resists for forming structures in LCD manufacturing processes, compositions for encapsulating electrical and electronic components, solder resists, magnetics Recording materials, micro mechanical parts, waveguides Optical switches, plating masks, etching masks, color test systems, glass fiber cable coatings, stencils for screen printing, materials for manufacturing three-dimensional objects by stereolithography, holographic recording materials, image recording materials, fine electronic circuits , Decoloring material, decoloring material for image recording material, decoloring material for image recording material using microcapsule, photoresist material for printed wiring board, photoresist material for UV and visible laser direct image system, printed circuit board It can be used for various applications such as a photoresist material and a protective film used for forming a dielectric layer in the sequential lamination of the above, and the application is not particularly limited.
本発明の硬化性組成物を用いた硬化物の製造方法について、好ましい塗布方法、硬化条件を下記に示す About the manufacturing method of the hardened | cured material using the curable composition of this invention, a preferable coating method and hardening conditions are shown below.
本発明の硬化性組成物の塗布方法は、ロールコーター、カーテンコーター、各種の印刷、浸漬等の公知の手段であり、ガラス、金属、紙、プラスチック等の支持基体上に適用される。また、一旦フィルム等の支持基体上に施した後、他の支持基体上に転写すること、即ちドライフィルムの形態として使用することもでき、その適用方法に制限はない。 The coating method of the curable composition of the present invention is a known means such as a roll coater, a curtain coater, various types of printing and dipping, and is applied on a supporting substrate such as glass, metal, paper, and plastic. Moreover, after applying on a support substrate such as a film, it can be transferred onto another support substrate, that is, used as a dry film, and the application method is not limited.
また、本発明の硬化性組成物を硬化させる際に用いられる活性光の光源としては、波長300〜450nmの光を発光するものを用いることができ、例えば、超高圧水銀、水銀蒸気アーク、カーボンアーク及びキセノンアーク等を用いることができる。 In addition, as the light source of the active light used when the curable composition of the present invention is cured, a light source that emits light having a wavelength of 300 to 450 nm can be used. For example, ultrahigh pressure mercury, mercury vapor arc, carbon An arc, a xenon arc, or the like can be used.
更に、露光光源にレーザー光を用いることにより、マスクを用いずに、コンピューター等のデジタル情報から直接画像を形成するレーザー直接描画法が、生産性のみならず、解像性や位置精度等の向上も図れることから有用であり、そのレーザー光としては、340〜430nmの波長の光が好適に使用されるが、アルゴンイオンレーザー、ヘリウムネオンレーザー、YAGレーザー、及び半導体レーザー等の可視から赤外領域の光を発するものも用いられる。これらのレーザーを使用する場合には、可視から赤外の当該領域を吸収する増感色素が加えられる。 Furthermore, by using laser light as the exposure light source, the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy. As the laser light, light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.
本発明の硬化性組成物を用いた硬化物は、硬化性塗料、ワニス、硬化性接着剤、プリント基板、或いはカラーテレビ、PCモニタ、携帯情報端末及びデジタルカメラ等のカラー表示の液晶表示パネルにおけるカラーフィルタ、CCDイメージセンサのカラーフィルタ、タッチパネル、プラズマ表示パネル用の電極材料、粉末コーティング、印刷インク、印刷版、接着剤、ゲルコート、電子工学用のフォトレジスト、電気メッキレジスト、エッチングレジスト、はんだレジスト、絶縁膜、ブラックマトリックス、種々の表示用途用のカラーフィルタ、プラズマ表示パネル、電気発光表示装置、及びLCDの製造工程において構造を形成するためのレジスト、電気及び電子部品を封入するための組成物、ソルダーレジスト、磁気記録材料、微小機械部品、導波路、光スイッチ、めっき用マスク、エッチングマスク、カラー試験系、ガラス繊維ケーブルコーティング、スクリーン印刷用ステンシル、ステレオリトグラフィによって三次元物体を製造するための材料、ホログラフィ記録用材料、画像記録材料、微細電子回路、脱色材料、画像記録材料のための脱色材料、マイクロカプセルを使用する画像記録材料用の脱色材料、印刷配線板用フォトレジスト材料、UV及び可視レーザー直接画像系用のフォトレジスト材料、プリント回路基板の逐次積層における誘電体層形成に使用するフォトレジスト材料及び保護膜等の各種の用途に使用することができ、その用途に特に制限はない。 A cured product using the curable composition of the present invention is a curable paint, varnish, curable adhesive, printed circuit board, or a color display liquid crystal display panel such as a color television, a PC monitor, a portable information terminal, and a digital camera. Color filters, color filters for CCD image sensors, touch panels, electrode materials for plasma display panels, powder coatings, printing inks, printing plates, adhesives, gel coats, photoresists for electronics, electroplating resists, etching resists, solder resists , Insulating film, black matrix, color filter for various display applications, plasma display panel, electroluminescent display device, and composition for encapsulating resist, electrical and electronic components for forming structures in the manufacturing process of LCD , Solder resist, magnetic recording material, micromachine Components, waveguides, optical switches, plating masks, etching masks, color test systems, glass fiber cable coatings, stencils for screen printing, materials for manufacturing 3D objects by stereolithography, holographic recording materials, image recording Materials, fine electronic circuits, bleaching materials, bleaching materials for image recording materials, bleaching materials for image recording materials using microcapsules, photoresist materials for printed wiring boards, photoresists for UV and visible laser direct imaging systems The material can be used for various applications such as a photoresist material and a protective film used for forming a dielectric layer in the sequential lamination of printed circuit boards, and the application is not particularly limited.
本発明の硬化性組成物は、黒色顔料を用いた場合、ブラックマトリックスを形成する目的で使用され、該ブラックマトリックスは、特に液晶表示パネル等の画像表示装置用の表示デバイス用カラーフィルタに有用である。 The curable composition of the present invention is used for the purpose of forming a black matrix when a black pigment is used, and the black matrix is particularly useful for a color filter for a display device for an image display device such as a liquid crystal display panel. is there.
上記ブラックマトリックスは、(1)本発明の硬化性組成物の塗膜を基板上に形成する工程、(2)該塗膜に所定のパターン形状を有するマスクを介して活性光を照射する工程、(3)露光後の被膜を現像液(特にアルカリ現像液)にて現像する工程、(4)現像後の該被膜を加熱する工程により好ましく形成される。また、本発明の硬化性組成物は、現像工程の無いインクジェット方式組成物としても有用である。
液晶表示パネル等に用いるカラーフィルタの製造は、本発明又はそれ以外の着色組成物を用いて、上記(1)〜(4)の工程を繰り返し行い、2色以上のパターンを組み合わせて作成することができる。
The black matrix includes (1) a step of forming a coating film of the curable composition of the present invention on a substrate, (2) a step of irradiating the coating film with active light through a mask having a predetermined pattern shape, (3) It is preferably formed by a step of developing the exposed film with a developer (particularly an alkali developer), and (4) a step of heating the film after development. The curable composition of the present invention is also useful as an ink jet composition without a development step.
Manufacture of color filters for use in liquid crystal display panels, etc. is made by repeating the above steps (1) to (4) using the present invention or other colored composition and combining two or more color patterns. Can do.
以下、実施例等を挙げて本発明を更に詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example etc. are given and this invention is demonstrated further in detail, this invention is not limited to these Examples.
[製造例1]重合性化合物No.1の調製
1,1−ビス〔4−(2,3−エポキシプロピルオキシ)フェニル〕インダンの184g、アクリル酸58g、2,6−ジ−tert−ブチル−p−クレゾール0.26g、テトラ−n−ブチルアンモニウムブロミド0.11g及びPGMEA105gを仕込み、120℃で16時間撹拌した。反応液を室温まで冷却し、PGMEA160g、ビフタル酸無水物59g及びテトラ−n−ブチルアンモニウムブロミド0.24gを加えて、120℃で4時間撹拌した。更に、テトラヒドロ無水フタル酸20gを加え、120℃で4時間、100℃で3時間、80℃で4時間、60℃で6時間、40℃で11時間撹拌した後、PGMEA128gを加えて、PGMEA溶液として重合性化合物No.1を得た(Mw=5000、Mn=2100、酸価(固形分)92.7mgKOH/g)。
[Production Example 1] polymerizable compound no. Preparation of 1 184 g of 1,1-bis [4- (2,3-epoxypropyloxy) phenyl] indane, 58 g of acrylic acid, 0.26 g of 2,6-di-tert-butyl-p-cresol, tetra-n -0.11 g of butylammonium bromide and 105 g of PGMEA were charged and stirred at 120 ° C for 16 hours. The reaction solution was cooled to room temperature, 160 g of PGMEA, 59 g of biphthalic anhydride and 0.24 g of tetra-n-butylammonium bromide were added, and the mixture was stirred at 120 ° C. for 4 hours. Further, 20 g of tetrahydrophthalic anhydride was added, and after stirring at 120 ° C. for 4 hours, at 100 ° C. for 3 hours, at 80 ° C. for 4 hours, at 60 ° C. for 6 hours, and at 40 ° C. for 11 hours, PGMEA 128 g was added to obtain a PGMEA solution As polymerizable compound No. 1 (Mw = 5000, Mn = 2100, acid value (solid content) 92.7 mgKOH / g) was obtained.
[製造例2]重合性化合物No.2の製造
9,9−ビス(4−グリシジルオキシフェニル)フルオレン75.0g、アクリル酸23.8g、2,6−ジ−t−ブチル−p−クレゾール0.273g、テトラブチルアンモニウムクロリド0.585g、及びPGMEA65.9gを仕込み、90℃で1時間、100℃ で1時間、110℃ で1時間及び120℃ で14時間撹拌した。室温まで冷却し、無水コハク酸25.9g、テトラブチルアンモニウムクロリド0.427g、及びPGMEA1.37gを加えて、100℃ で5時間撹拌した。さらに、9,9−ビス(4−グリシジルオキシフェニル)フルオレン30.0g、2,6−ジ−t−ブチル−p−クレゾール0.269g、及びPGMEA1.50gを加えて、90℃ で90分、120℃ で4時間撹拌後、PGMEA122.2gを加えて、PGMEA溶液として目的物である重合性化合物No.2を得た(Mw=4190、Mn=2170,酸価(固形分)52mg・KOH/g)
[Production Example 2] Polymerizable Compound No. Production of 2 9,9-bis (4-glycidyloxyphenyl) fluorene 75.0 g, acrylic acid 23.8 g, 2,6-di-t-butyl-p-cresol 0.273 g, tetrabutylammonium chloride 0.585 g And PGMEA 65.9 g, and stirred at 90 ° C. for 1 hour, 100 ° C. for 1 hour, 110 ° C. for 1 hour and 120 ° C. for 14 hours. After cooling to room temperature, 25.9 g of succinic anhydride, 0.427 g of tetrabutylammonium chloride, and 1.37 g of PGMEA were added, and the mixture was stirred at 100 ° C. for 5 hours. Further, 90.0 g of 9,9-bis (4-glycidyloxyphenyl) fluorene, 0.269 g of 2,6-di-t-butyl-p-cresol and 1.50 g of PGMEA were added, and 90 minutes at 90 ° C. After stirring at 120 ° C. for 4 hours, 122.2 g of PGMEA was added, and a polymerizable compound No. 1 as a target product as a PGMEA solution was added. 2 (Mw = 4190, Mn = 2170, acid value (solid content) 52 mg · KOH / g)
[実施例1〜16及び比較例1〜6]硬化性組成物の調製
[表1]〜[表3]の配合に従って各成分を混合し、硬化性組成物(実施例1〜16及び比較例1〜6)を得た。尚、数字は質量部を表す。また[表1]〜[表3]中の成分(A)〜(D)成分及び溶剤は下記のものを使用した。
[Examples 1 to 16 and Comparative Examples 1 to 6] Preparation of curable compositions
Each component was mixed according to the mixing | blending of [Table 1]-[Table 3], and the curable composition (Examples 1-16 and Comparative Examples 1-6) was obtained. In addition, a number represents a mass part. In addition, the following components (A) to (D) and the solvents in [Table 1] to [Table 3] were used.
A−1:化合物No.A1
A−2:化合物No.A2
A−3:化合物No.A3
A−4:化合物No.A4
A'−5:KBE−9007 (イソシアネート基含有アルコキシシラン;信越化学社製)
A'−6:KBM−403 (エポキシ基含有アルコキシシラン;信越化学社製)
B−1:重合性不飽和化合物No.1 (フェニルインダン骨格 PGMEA 55wt%含有)
B−2:重合性不飽和化合物No.2 (フルオレン骨格 PGMEA 55wt%含有)
B−3:カヤラッドDPHA(ジペンタエリスリトールヘキサアクリレート;日本化薬社製)
B−4:アデカレジンEP−4000S (BPA-PO型グリシジルエーテル;ADEKA製)
B−5:EHPE−3150 (脂環式エポキシ化合物;ダイセル製)
C−1:アデカアークルズNCI−831(光ラジカル開始剤;ADEKA社製)
C−2:IRGACURE OXE 02 (光ラジカル開始剤;BASF社製)
C−3:アデカオプトマーSP−150 (光カチオン開始剤;ADEKA社製)
C−4:アデカオプトンCP−66 (熱カチオン開始剤;ADEKA社製)
D−1:表面処理なしカーボンブラック分散液
(カーボンブラック20wt%、PGMEA76.2wt%含有)
E−1:PGMEA
A-1: Compound No. A1
A-2: Compound No. A2
A-3: Compound No. A3
A-4: Compound No. A4
A'-5: KBE-9007 (isocyanate group-containing alkoxysilane; manufactured by Shin-Etsu Chemical Co., Ltd.)
A′-6: KBM-403 (epoxy group-containing alkoxysilane; manufactured by Shin-Etsu Chemical Co., Ltd.)
B-1: Polymerizable unsaturated compound No. 1 (Phenylindane skeleton containing PGMEA 55 wt%)
B-2: Polymerizable unsaturated compound No. 2 (containing 55 wt% fluorene skeleton PGMEA)
B-3: Kayalad DPHA (dipentaerythritol hexaacrylate; manufactured by Nippon Kayaku Co., Ltd.)
B-4: Adeka Resin EP-4000S (BPA-PO type glycidyl ether; manufactured by ADEKA)
B-5: EHPE-3150 (alicyclic epoxy compound; manufactured by Daicel)
C-1: Adeka Arcles NCI-831 (photo radical initiator; manufactured by ADEKA)
C-2: IRGACURE OXE 02 (photo radical initiator; manufactured by BASF)
C-3: Adekaoptomer SP-150 (photocation initiator; manufactured by ADEKA)
C-4: Adeka Opton CP-66 (thermal cation initiator; manufactured by ADEKA)
D-1: Carbon black dispersion without surface treatment (carbon black 20 wt%, PGMEA 76.2 wt% contained)
E-1: PGMEA
[評価例1〜16及び比較評価例1〜6]
基板上にγ−グリシドキシプロピルメチルエトキシシランをスピンコートして良くスピン乾燥させた後、実施例1〜16で得られた硬化性組成物No.1〜No.16及び比較例1〜6で得られた比較硬化性組成物No.1〜No.6をスピンコート(1300rpm、50秒間)し乾燥させた。70℃で20分間プリベークを行った後、ポリビニルアルコール5%溶液をコートして酸素遮断膜とした。70℃ にて20分間の乾燥後、所定のマスクを用い、光源として超高圧水銀ランプを用いて露光後、2.5%炭酸ナトリウム溶液に25℃で30秒間浸漬して現像し、良く水洗した。水洗乾燥後、230℃ で1時間ベークしてパターンを定着させた。得られたパターンについて、以下の感度、OD値、体積抵抗率の測定を行った。結果を[表1]〜[表3]に示す。
(シール強度)
ガラス基板に6mmx3.5mmの面積で熱硬化接着剤(シール剤:三井化学社製XN-21S)を塗布し、硬化性組成物層のあるガラス基盤と貼りあわせ、接着剤を硬化させた。貼りあわされた基板を120℃、2atm、相対湿度100%の条件の高温高湿装置内に5時間静置した。このサンプルについて島津製EZ-Graphにて3点支持曲げ試験を実施し、密着強度を測定した。
(碁盤目試験)
硬化性組成物層のある基盤を120℃、2atm、相対湿度100%の条件にて高温高湿装置内に5時間静置した。JISK5600−5−6に従って、カッターにて硬化膜に1mm2のマスを100個作成した。その上にポリイミドテープを貼り付け、硬化膜がハガレの割合を観察した。全くハガレなかったものを◎、1マスもハガレなかったが、マスの角が一マス以上でもかけたものを○、1マス以上ハガレたものを×とした。
(保存安定性)
サンプル調整後のレジスト液をスクリュー管瓶に充填し、40℃、3日間静置した。静置後のレジスト液の粘度を測定し、粘度変化が5%以内であれば○、5%以上あるものを×とした。
(OD値)
得られた膜のOD値をマクベス透過濃度計を用いて測定し、該OD値をポストベイク後の膜厚で割って、膜厚あたりのOD値を算出した。
(感度)
露光量が30mJ/cm2で現像後のパターンの定着が良好となるものをAとし、露光量が30mJ/cm2で現像後のパターンの定着が不良で露光量が40mJ/cm2において現像後のパターンの定着が良好となるものをB、100mJ/cm2以上の露光が必要なものをCとした。
[Evaluation Examples 1 to 16 and Comparative Evaluation Examples 1 to 6]
After spin coating γ-glycidoxypropylmethylethoxysilane on the substrate and spin drying well, the curable compositions Nos. 1 to 16 obtained in Examples 1 to 16 were used. 1-No. 16 and comparative curable composition No. obtained in Comparative Examples 1-6. 1-No. 6 was spin-coated (1300 rpm, 50 seconds) and dried. After pre-baking at 70 ° C. for 20 minutes, a 5% polyvinyl alcohol solution was coated to form an oxygen barrier film. After drying at 70 ° C. for 20 minutes, using a predetermined mask, using an ultra-high pressure mercury lamp as a light source, exposure was performed, soaked in a 2.5% sodium carbonate solution at 25 ° C. for 30 seconds, developed, and washed thoroughly with water. . After washing with water and drying, the pattern was fixed by baking at 230 ° C. for 1 hour. About the obtained pattern, the following sensitivity, OD value, and volume resistivity were measured. The results are shown in [Table 1] to [Table 3].
(Seal strength)
A thermosetting adhesive (sealing agent: XN-21S manufactured by Mitsui Chemicals, Inc.) was applied to a glass substrate in an area of 6 mm × 3.5 mm, and was bonded to a glass substrate having a curable composition layer, and the adhesive was cured. The bonded substrate was allowed to stand for 5 hours in a high temperature and high humidity apparatus under conditions of 120 ° C., 2 atm, and relative humidity 100%. This sample was subjected to a three-point support bending test using Shimadzu EZ-Graph, and the adhesion strength was measured.
(Cross cut test)
The substrate with the curable composition layer was allowed to stand in a high-temperature and high-humidity device for 5 hours under the conditions of 120 ° C., 2 atm, and relative humidity 100%. In accordance with JISK5600-5-6, 100 squares of 1 mm 2 were formed on the cured film with a cutter. A polyimide tape was affixed thereon, and the rate of peeling of the cured film was observed. A sample that was not peeled off at all was marked as ◎, but a square was not peeled off.
(Storage stability)
The resist solution after sample preparation was filled in a screw tube bottle and allowed to stand at 40 ° C. for 3 days. The viscosity of the resist solution after standing was measured. If the change in viscosity was within 5%, ○ was 5% or more.
(OD value)
The OD value of the obtained film was measured using a Macbeth transmission densitometer, and the OD value per unit film thickness was calculated by dividing the OD value by the film thickness after post-baking.
(sensitivity)
When the exposure amount is 30 mJ / cm 2 and the pattern is fixed well after development, A is used. After the development when the exposure amount is 30 mJ / cm 2 and the pattern after development is poorly fixed and the exposure amount is 40 mJ / cm 2 . B was used for fixing the pattern, and C was used for exposure requiring 100 mJ / cm 2 or more.
以上の結果より、本発明の硬化性組成物は耐湿熱試験後の密着強度が良好で保存安定性に優れることが明らかである。また、着色剤としてカーボンブラックを添加した硬化性組成物においては遮光性と感度を維持した上で耐湿熱試験後の密着強度が良好で保存安定性に優れている。よって、本発明の硬化性組成物は、電子材料用硬化性樹脂組成物、特にブラックマトリックスに有用である。 From the above results, it is clear that the curable composition of the present invention has good adhesion strength after the wet heat resistance test and excellent storage stability. Moreover, in the curable composition which added carbon black as a coloring agent, while maintaining light-shielding property and sensitivity, the adhesive strength after a moist heat test is good, and it is excellent in storage stability. Therefore, the curable composition of this invention is useful for the curable resin composition for electronic materials, especially a black matrix.
Claims (8)
開始剤(C)を含有する硬化性組成物。
り、R1が炭素数1〜20のアルキル基であり、かつ置換基としてエポキシ基又はイソシアネート基を有する基を1つ以上含有するものであることを特徴とする請求項1に記載の硬化性組成物。 In the general formula (I), the allylsilane compound (A) is a number of 1 to 3, R 1 is an alkyl group having 1 to 20 carbon atoms, and has an epoxy group or an isocyanate group as a substituent. The curable composition according to claim 1, which contains one or more groups.
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