JP2016135852A - 光硬化性組成物 - Google Patents
光硬化性組成物 Download PDFInfo
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- JP2016135852A JP2016135852A JP2015256085A JP2015256085A JP2016135852A JP 2016135852 A JP2016135852 A JP 2016135852A JP 2015256085 A JP2015256085 A JP 2015256085A JP 2015256085 A JP2015256085 A JP 2015256085A JP 2016135852 A JP2016135852 A JP 2016135852A
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- meth
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- acrylate
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- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 229920000642 polymer Polymers 0.000 claims abstract description 169
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 146
- 229920000620 organic polymer Polymers 0.000 claims abstract description 49
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 13
- 150000003377 silicon compounds Chemical class 0.000 claims abstract description 12
- 229910008284 Si—F Inorganic materials 0.000 claims abstract description 11
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 10
- 239000011231 conductive filler Substances 0.000 claims abstract description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 43
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 15
- 230000002062 proliferating effect Effects 0.000 claims description 13
- 239000000853 adhesive Substances 0.000 claims description 9
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- 230000001678 irradiating effect Effects 0.000 claims description 7
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 229920000193 polymethacrylate Polymers 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- -1 amine compound Chemical class 0.000 description 402
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 148
- 229940048053 acrylate Drugs 0.000 description 148
- 150000001875 compounds Chemical class 0.000 description 86
- 125000004432 carbon atom Chemical group C* 0.000 description 72
- 238000000034 method Methods 0.000 description 70
- 125000000217 alkyl group Chemical group 0.000 description 48
- 239000000178 monomer Substances 0.000 description 47
- 239000000047 product Substances 0.000 description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 40
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 33
- 229920002313 fluoropolymer Polymers 0.000 description 32
- 239000002585 base Substances 0.000 description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 30
- 125000003118 aryl group Chemical group 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- 238000001723 curing Methods 0.000 description 26
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 25
- 239000012025 fluorinating agent Substances 0.000 description 25
- 125000004122 cyclic group Chemical group 0.000 description 23
- 238000010526 radical polymerization reaction Methods 0.000 description 23
- 239000003054 catalyst Substances 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 22
- 125000003545 alkoxy group Chemical group 0.000 description 21
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- 125000003277 amino group Chemical group 0.000 description 20
- 229910052731 fluorine Inorganic materials 0.000 description 20
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 18
- 125000002947 alkylene group Chemical group 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 17
- 235000019000 fluorine Nutrition 0.000 description 17
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
- 239000011737 fluorine Substances 0.000 description 15
- 125000000524 functional group Chemical group 0.000 description 15
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- 150000003254 radicals Chemical class 0.000 description 15
- 229910052710 silicon Inorganic materials 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
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- 125000001153 fluoro group Chemical group F* 0.000 description 14
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 14
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 12
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical group FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
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- 239000010703 silicon Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
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- 238000010438 heat treatment Methods 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 9
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 125000006574 non-aromatic ring group Chemical group 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
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- 238000013329 compounding Methods 0.000 description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
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- 230000000704 physical effect Effects 0.000 description 7
- 229920000098 polyolefin Polymers 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- 229910015900 BF3 Inorganic materials 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
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- 125000000753 cycloalkyl group Chemical group 0.000 description 6
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- UZIAQVMNAXPCJQ-UHFFFAOYSA-N triethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C(C)=C UZIAQVMNAXPCJQ-UHFFFAOYSA-N 0.000 description 1
- QYBKVVRRGQSGDC-UHFFFAOYSA-N triethyl methyl silicate Chemical compound CCO[Si](OC)(OCC)OCC QYBKVVRRGQSGDC-UHFFFAOYSA-N 0.000 description 1
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- BHOCBLDBJFCBQS-UHFFFAOYSA-N trifluoro(methyl)silane Chemical compound C[Si](F)(F)F BHOCBLDBJFCBQS-UHFFFAOYSA-N 0.000 description 1
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- CJYXHAUSMDGBBU-UHFFFAOYSA-N trifluoro-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound F[Si](F)(F)CCCOCC1CO1 CJYXHAUSMDGBBU-UHFFFAOYSA-N 0.000 description 1
- DALOGFFOSLUGET-UHFFFAOYSA-N trifluoromethoxysilane Chemical compound FC(F)(F)O[SiH3] DALOGFFOSLUGET-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
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- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
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- 238000009849 vacuum degassing Methods 0.000 description 1
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- 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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- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- Adhesives Or Adhesive Processes (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
Description
本発明の硬化物は、本発明の硬化物の製造方法により形成されてなる硬化物である。
−R2−O−・・・(4)
前記一般式(4)中、R2は炭素数1〜14の直鎖状もしくは分岐アルキレン基であり、炭素数1〜14の、さらには2〜4の、直鎖状もしくは分岐アルキレン基が好ましい。
−CH2O−、−CH2CH2O−、−CH2CH(CH3)O−、−CH2CH(C2H5)O−、−CH2C(CH3)2O−、−CH2CH2CH2CH2O−
等が挙げられる。ポリオキシアルキレン系重合体の主鎖骨格は、1種類だけの繰り返し単位からなってもよいし、2種類以上の繰り返し単位からなってもよい。
−CH2−C(R3)(COOR4)− ・・・(5)
(式中、R3は水素原子またはメチル基、R4は炭素数1〜5のアルキル基を示す)で表される(メタ)アクリル酸エステル単量体単位と、下記一般式(6):
−CH2−C(R3)(COOR5)− ・・・(6)
(式中、R3は前記に同じ、R5は炭素数6以上のアルキル基を示す)で表される(メタ)アクリル酸エステル単量体単位からなる共重合体に、架橋性珪素基を有するポリオキシアルキレン系重合体をブレンドして製造する方法である。
これら塩基は単独で用いてもよく、2種以上組み合わせて用いてもよい。
グアニジン系化合物としては、グアニジン、1,1,3,3−テトラメチルグアニジン、1−ブチルグアニジン、1−フェニルグアニジン、1−o−トリルグアニジン、1,3−ジフェニルグアニジンなどを挙げることができる。
ビグアニド系化合物としては、ブチルビグアニド、1−o−トリルビグアニドや1−フェニルビグアニドを挙げることができる。
R52及びR53は、互いに独立して、水素、C1−C18アルキル、C3−C18アルケニル、C3−C18アルキニル又はフェニルであり、そしてもしR52が水素又はC1−C18アルキルであれば、R53は、更に、基−CO−R64(式中、R64は、C1−C18アルキル又はフェニルである)であるか;或いは、R51とR53は、カルボニル基及びR53が結合しているC原子と一緒になって、ベンゾシクロペンタノン基を形成する。
R54およびR56は、一緒になって、非置換であるか、または1個以上のC1〜C4アルキル基によって置換されているC2〜C12アルキレンブリッジを形成する。R55およびR57は、一緒になって、R54およびR56とは独立して、非置換であるか、または1個以上のC1〜C4アルキル基によって置換されているC2〜C12アルキレンブリッジを形成する。R54とR56が、一緒になって、C3アルキレン橋を形成し、R55とR57が、一緒になって、プロピレン又はペンチレンであることが好ましい。
R66は炭素原子数1〜12のアルキル基;−OH、−炭素原子数1〜4のアルコキシ、−CNもしくは−COO(炭素原子数1〜4のアルキル)で置換された炭素原子数2〜4のアルキル基を表すか、または、R66は炭素原子数3〜5のアルケニル基、炭素原子数5〜12のシクロアルキル基またはフェニル−炭素原子数1〜3のアルキル基を表す。R67は炭素原子数1〜12のアルキル基;または−OH、−炭素原子数1〜4のアルコキシ基、−CNもしくは−COO(炭素原子数1〜4のアルキル)で置換された炭素原子数2〜4のアルキル基を表すかまたはR67は炭素原子数3〜5のアルケニル基、炭素原子数5〜12のシクロアルキル基、フェニル−炭素原子数1〜3のアルキル基、または、未置換であるかまたは炭素原子数1〜12のアルキル基、炭素原子数1〜4のアルコキシ基もしくは−COO(炭素原子数1〜4のアルキル)によって置換されたフェニル基を表すか、あるいはR67はRR66と一緒になって炭素原子数1〜7のアルキレン基、フェニル−炭素原子数1〜4のアルキレン基、o−キシリレン基、2−ブテニレン基または炭素原子数2もしくは3のオキサアルキレン基を表すか、あるいはR66およびR67は一緒になって−O−、−S−もしくは−CO−で中断され得る炭素原子数4〜7のアルキレン基を表すか、またはR66およびR67は一緒になってOH、炭素原子数1〜4のアルコキシ基もしくは−COO(炭素原子数1〜4のアルキル)で置換され得る炭素原子数3〜7のアルキレン基を表す。R66およびR67が複数存在する場合それらは同じであっても異なっていてもよい。
Y1は下記式(V)で示される2価の基、−N(R68)−又は−N(R68)−R69−N(R68)−で示される2価の基を表し、R68は炭素原子数1〜8のアルキル基、炭素原子数3〜5のアルケニル基、フェニル−炭素原子数1〜3のアルキル基、炭素原子数1〜4のヒドロキシアルキル基もしくはフェニル基を表し、R69は1もしくはそれ以上の−O−または−S−により中断され得る枝分かれしていないまたは枝分かれした炭素原子数2〜16のアルキレン基を表す。
Y2は炭素原子数1〜6のアルキレン基、シクロヘキシレン基もしくは直接結合を表す。
R70〜R72は、それぞれ互いに独立に、水素、C1〜C18アルキル、C3〜C18アルケニル、C3〜C18アルキニルもしくはフェニルであり;またはR70とR71および/もしくはR72とR71が、互いに独立にC2〜C12アルキレン架橋を形成しているか;あるいはR70〜R72が、結合している窒素原子とともに、P1、P2、P<t/4>型のホスファゼン塩基を、または、下記構造式(a)、(b)、(c)、(d)、(e)、(f)もしくは(g)の基を形成している。
R73およびR74は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基又はハロゲン原子、炭素数1〜20のアルコキシ基、ニトロ基、カルボキシル基、水酸基、メルカプト基、炭素数1〜20のアルキルチオ基、炭素数1〜20のアルキルシリル基、炭素数1〜20のアシル基、アミノ基、シアノ基、炭素数1〜20のアルキル基、フェニル基、ナフチル基、フェノキシ基及びフェ二ルチオ基の群から選ばれる基で置換されていてもよいフェニル基を表し、R73及びR74は互いに結合して環構造を形成していてもよい。
前記光塩基発生剤(B)の配合割合は特に制限はないが、(A)架橋性珪素基含有有機重合体100質量部に対して、0.01〜50質量部が好ましく、0.01〜40質量部がより好ましく、0.1〜30質量部がさらに好ましい。
(式(7)において、R11はそれぞれ独立して、置換あるいは非置換の炭素原子数1〜20の炭化水素基、またはR12SiO−(R12はそれぞれ独立に、炭素原子数1〜20の置換あるいは非置換の炭化水素基、又はフッ素原子である)で示されるオルガノシロキシ基のいずれかを示す。dは1〜3のいずれかであり、dが3であることが好ましい。R11及びR12が複数存在する場合、それらは同じであっても異なっていてもよい。)
(式(8)中、R11及びdはそれぞれ式(7)と同じであり、Zはそれぞれ独立して水酸基又はフッ素以外の加水分解性基であり、eは0〜2のいずれかであり、fは0〜2のいずれかであり、d+e+fは3である。R11、R12及びZが複数存在する場合、それらは同じであっても異なっていてもよい。)
また、合成の容易さからフルオロジメチルシリル基、ジフルオロメチルシリル基、トリフルオロシリル基、フルオロメトキシメチルシリル基、フルオロエトキシメチルシリル基、フルオロメトキシエチルシリル基、フルオロジメトキシシリル基、フルオロジエトキシシリル基、ジフルオロメトキシシリル基、ジフルオロエトキシシリル基がより好ましく、安定性の観点からフルオロジメチルシリル基、ジフルオロメチルシリル基、トリフルオロシリル基などのフッ素以外に加水分解性基を持たないケイ素基がさらに好ましく、硬化性の高さからは、ジフルオロメチルシリル基、ジフルオロメトキシシリル基、ジフルオロエトキシシリル基、トリフルオロシリル基など、ケイ素基上に2個ないし3個のフッ素が置換したケイ素基が好ましく、トリフルオロシリル基が最も好ましい。
−SiR11 3−pZp ・・・(9)
(式(9)中、R11及びZはそれぞれ式(8)と同じであり、pは1〜3のいずれかである。)
ハロシリル基のフッ素化に使用されるフッ素化剤の具体例としては、特に限定されず、例えば、AgBF4、SbF3、ZnF2、NaF、KF、CsF、NH4F、CuF2、NaSiF6、NaPF6、NaSbF6、NaBF4、Me3SnF、KF(HF)1.5〜5などが挙げられる。
ヒドロシリル基のフッ素化に使用されるフッ素化剤の具体例としては、特に限定されず、例えば、AgF、PF5、Ph3CBF4、SbF3、NOBF4、NO2BF4などが挙げられる。
シロキサン結合を有する化合物はBF3などにより開裂し、フルオロシリル基が得られる。
有機重合体中のSiF結合の位置も特に制限はなく、重合体分子内のいずれの部位にあっても効果を発揮し、主鎖または側鎖の末端であれば−SiR’2F、重合体の主鎖に組み込まれていれば、−SiR’F−または≡SiF(R’はそれぞれ独立に、任意の基)の形で表される。
主鎖又は側鎖の末端にSi−F結合を有する有機重合体としては、前述した式(8)で示されるフルオロシリル基を有する重合体が好適である。フルオロシリル基が重合体の主鎖中に組み込まれたものの例としては、−Si(CH3)F−、−Si(C6H5)F−、−SiF2−、≡SiFなどが挙げられる。
(イ)分子中に水酸基、エポキシ基やイソシアネート基等の官能基を有する重合体に、この官能基に対して反応性を示す官能基およびフルオロシリル基を有する化合物を反応させる方法。たとえば、末端に水酸基を有する重合体とイソシアネートプロピルジフルオロメチルシランを反応させる方法や、末端にSiOH基を有する重合体とジフルオロジエトキシシランを反応させる方法が挙げられる。
(ロ)分子中に不飽和基を含有する重合体に、フルオロシリル基を有するヒドロシランを作用させてヒドロシリル化する方法。たとえば、末端にアリル基を有する重合体に、ジフルオロメチルヒドロシランを反応させる方法が挙げられる。
(ハ)不飽和基を含有する重合体に、メルカプト基およびフルオロシリル基を有する化合物を反応させる方法。たとえば、末端にアリル基を有する重合体に、メルカプトプロピルジフルオロメチルシランを反応させる方法が挙げられる。
フッ素化剤としては、例えば、前述したフッ素化剤が挙げられ、中でも、BF3エーテル錯体、BF3アルコール錯体、BF3二水和物は活性が高く、効率よくフッ素化が進行し、さらに副生成物に塩等が生じず、後処理が容易であるためにより好ましく、BF3エーテル錯体が特に好ましい。
さらに、BF3エーテル錯体によるフッ素化は、加熱しなくても反応が進行するが、より効率よくフッ素化を行なうためには、加熱することが好ましい。加熱温度としては50℃以上150℃以下が好ましく、60℃以上130℃がより好ましい。50℃以下であると反応が効率よく進行せず、フッ素化に時間がかかる場合がある。150℃以上であるとフッ素化ポリマーが分解する虞がある。BF3錯体によるフッ素化において、用いる重合体(X)の種類によっては着色が起こる場合があるが、着色の抑制の点から、BF3アルコール錯体、BF3二水和物を用いることが好ましい。
前記(D)活性エネルギー線開裂型ラジカル発生剤の配合割合は特に制限はないが、(A)架橋性珪素基含有有機重合体100質量部に対して、0.01〜20質量部が好ましく、0.01〜10質量部がより好ましく、0.1〜5質量部がさらに好ましい。これら活性エネルギー線開裂型ラジカル発生剤は単独で用いてもよく、2種以上を併用しても良い。
前記三フッ化ホウ素のアミン錯体の市販品としては、例えば、エアプロダクツジャパン株式会社製のアンカー1040、アンカー1115、アンカー1170、アンカー1222、BAK1171等が挙げられる。
これらの中でも、多価フルオロ化合物のアルカリ金属塩における多価フルオロ化合物成分としては、テトラフルオロホウ酸又はヘキサフルオロリン酸が好ましい。また、多価フルオロ化合物のアルカリ金属塩におけるアルカリ金属としては、リチウム、ナトリウム及びカリウムからなる群から選ばれる一種以上のアルカリ金属であることが好ましい。
炭素数1〜20の炭化水素基としては、アルキル基が好ましく、炭素数1〜3のアルキル基がより好ましく、直鎖状でも分岐を有していても良い。アルキル基としては、水酸基、芳香族基及びジアミノアルキル基をさらに有するアルキル基であっても良い。
アルキル基の具体例としては、メチル基、プロピル基、ブチル基、ブチル基及びヘキシル基等が挙げられる。
水酸基を有するアルキル基としては、ヒドロキシメチル基、ヒドロキシエチル基及びヒドロキシプロピル基等を挙げることができる。
芳香族基を有するアルキル基としては、ベンジル基等を挙げることができる。
ジアルキルアミノアルキル基としては、N,N−ジメチルアミノエチル基及びN,N−ジメチルアミノプロピル等を挙げることができる。
トキシシリル)プロピル]エチレンジアミン等のジアミン,γ−(2−(2−アミノエチル)アミノエチル)アミノプロピルトリメトキシシラン等のトリアミンなどが挙げられる。
[前記式(17)において、Aは直接結合又は2価の連結基であり、Q’は環状構造含有基である。直接結合とは、Q’が連結基を介することなく、Zに直接結合していることを意味する。Aにおける2価の連結基としては、例えば、それぞれ置換基を有していてもよい、アルキレン基、カルボニル基、エーテル結合、エステル結合、−CONH−基、またはこれらの組み合わせを含む2価の連結基等が挙げられ、置換基を含んでいてもよいアルキレン基やカルボニル基及びそれらの組合せが好ましい。また、Aの置換基が環状構造を有していてもよく、また、置換基同士が結合し、環状構造を形成していてもよい。該環状構造としては、例えば、Q’と同様のものが挙げられる。
前記Q’における環状構造は、単環及び複数の環のいずれもよく、また、単素環式及び複素環式のいずれでもよいが、ビニル基やカルボニル基、イミノ基等の官能基を含んでいることが好ましく、芳香族性を示す環状構造を有していることがより好ましい。前記Q’としては、例えば、それぞれ置換基を有していてもよい、アリール基,アリールオキシ基,窒素や酸素、硫黄等のヘテロ原子を1種以上含む複素環基,カルボニル基が結合した環状構造を含む基やこれらの組合せ及びこれらの縮合環等が挙げられる。また、置換基がさらに環状構造を有していてもよい。また、Aの置換基とQ’とが結合していてもよい。]
また、本発明の製品の製造方法は、本発明の光硬化性組成物を用いて製造することを特徴とする。本発明の製品は、該方法を用いて製造されてなる製品であり、電子回路、電子部品、建材、自動車等に好適に利用可能である。
数平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)により下記条件で測定した。本発明において、該測定条件でGPCにより測定し、標準ポリエチレングリコールで換算した最大頻度の分子量を数平均分子量と称する。
・分析装置:Alliance(Waters社製)、2410型示差屈折検出器(Waters社製)、996型多波長検出器(Waters社製)、Milleniamデータ処理装置(Waters社製)
・カラム:Plgel GUARD+5μmMixed−C×3本(50×7.5mm,300×7.5mm:PolymerLab社製)
・流速:1mL/分
・換算したポリマー:ポリエチレングリコール
・測定温度:40℃
・GPC測定時の溶媒:THF
NMR及びIRの測定は、下記測定装置を用いて行った。
FT−NMR測定装置:日本電子(株)製JNM−ECA500(500MHz)
FT−IR測定装置:日本分光(株)製FT−IR460Plus
攪拌装置、窒素ガス導入管、温度計および環流冷却器を備えたフラスコに、エチレングリコールを開始剤とし、亜鉛ヘキサシアノコバルテート−グライム錯体触媒の存在下、プロピレンオキシドを反応させ、ポリオキシプロピレントリオールを得た。得られたポリオキシプロピレントリオールにナトリウムメトキシドのメタノール溶液を添加し、加熱減圧下メタノールを留去してポリオキシプロピレントリオールの末端水酸基をナトリウムアルコキシドに変換し、ポリオキシアルキレン系重合体M1を得た。
攪拌装置、窒素ガス導入管、温度計および環流冷却器を備えた新しいフラスコに、分子量約2,000のポリオキシプロピレンジオールを開始剤とし、亜鉛ヘキサシアノコバルテート−グライム錯体触媒の存在下、プロピレンオキシドを反応させて得られた水酸基価換算分子量14500、かつ分子量分布1.3のポリオキシプロピレンジオールを得た。得られたポリオキシプロピレンジオールにナトリウムメトキシドのメタノール溶液を添加し、加熱減圧下メタノールを留去してポリオキシプロピレンジオールの末端水酸基をナトリウムアルコキシドに変換し、ポリオキシアルキレン系重合体M2を得た。
得られた末端にメチルジメトキシシリル基を有するポリオキシアルキレン系重合体A2の分子量をGPCにより測定した結果、ピークトップ分子量は15000、分子量分布1.3であった。H1−NMR測定により末端のメチルジメトキシシリル基は1分子あたり1.7個であった。
表1に示す配合割合にて、攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、合成例1で得たポリオキシアルキレン系重合体Aを添加し、加熱(100℃)、脱気、撹拌を2時間することによって脱水をした。冷却後、合成例2で得たフッ素化ポリマーC、光塩基発生剤、活性エネルギー線開裂型ラジカル発生剤、強塩基触媒をそれぞれ添加し、混合撹拌することにより光硬化性組成物、及び硬化性組成物を調製した。
※1 PBG−SA2(サンアプロ(株)製、活性エネルギー線の照射で1,8−ジアザビシクロ(5.4.0)ウンデセン−7が発生する光塩基発生剤、プロピレンカーボネート溶液で20質量%に希釈して使用。表1では、固形分の質量部を記載している。)
※2 Irgacure(登録商標)379EG(BASF社製、2−(ジメチルアミノ)−2−[(4−メチルフェニル)メチル]−1−[4−(4−モルホリニル)フェニル]−1−ブタノン)、プロピレンカーボネート溶液で50質量%に希釈して使用。表1では、固形分の質量部を記載している。)
※3 Irgacure(登録商標)907(BASF社製、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ン−1−オン)、プロピレンカーボネート溶液で50質量%に希釈して使用。表1では、固形分の質量部を記載している。)
※4 NBC−101(みどり化学(株)製、N−(2−メチル−2−フェニルプロピオニルオキシ)−N−シクロ
ヘキシルアミン、プロピレンカーボネート溶液で50質量%に希釈して使用。表1では、固形分の質量部を記載している。)
※5 Irgacure(登録商標)1173(BASF社製、活性エネルギー線開裂型ラジカル発生剤、2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン。
※6 DBU(1,8−ジアザビシクロ(5.4.0)ウンデセン−7)。
500nm以下の波長をカットするフィルムを張り付けた蛍光灯下で、23℃50%RHの環境下でスクリーン印刷機を用いて実施例1〜6、比較例1〜3で調製した組成物のUV未照射時の作業性試験を行った。
スクリーン速度50mm/secでPETフィルムへの連続塗布を行い、指触にて液状の場合を作業可能、硬化している場合を作業不可とし、スクリーン印刷作業が可能な時間を測定する。
8時間以上作業可能な場合を◎、4時間以上8時間未満作業可能な場合を○、4時間未満で作業不可となった場合を×とした。
アクリル板(25mm×75mm×3mm)上に実施例1〜6、比較例1〜3の光硬化性組成物を約100μm厚に塗布し、UV照射後[照射条件:メタルハライドランプ、照度330mW/cm2、積算光量:3000mJ/cm2]、23℃50%RHの環境下において、光硬化性組成物表面を指触にて硬化具合を確認する。液状の場合を○、ゲル化(液状と固体の中間)している場合を△、硬化している場合を×とした。
アクリル板(25mm×75mm×3mm)上に実施例1〜6、比較例1〜3の光硬化性組成物を25mm×25mmの面積に約100μm厚に塗布し、UV照射[照射条件:メタルハライドランプ、照度:330mW/cm2、積算光量:3000mJ/cm2]する。
UV照射後23℃50%RHの環境下において、同じ大きさのアクリル板を貼り合わせて目玉クリップ小により圧締し、貼り合わせ試験を行う。UV照射30秒以上経過後であっても目視で気泡がなく貼り合わせが可能だった場合を○、30秒未満で貼り合わせが不可能だった場合、または気泡が発生している場合を×とした。
UV照射が必要な光硬化性組成物(実施例1〜6、比較例1〜3)は、直径20mm、高さ7mmの円筒形容器に厚みが7mmになるように光硬化性組成物を注ぎ、UV照射[照射条件:メタルハライドランプ、照度:330mW/cm2、積算光量:3000mJ/cm2]後直ちに、暗室下23℃50%RHの環境下において、30秒ごとに指触にて表面がべたつかなくなり、硬化するまでの時間を測定した。
UV照射が不要な硬化性組成物(比較例4〜5)は、直径20mm、高さ7mmの円筒形容器に厚みが7mmになるように硬化性組成物を注ぎ、23℃50%RHの環境下において、30秒ごとに指触にて表面がべたつかなくなり、硬化するまでの時間を測定した。
UV照射が必要な光硬化性組成物(実施例1〜6、比較例1〜3)は、直径20mm、高さ7mmの円筒形容器(ポリプロピレン)に厚みが7mmになるように光硬化性組成物を注ぎ、UV照射[照射条件:メタルハライドランプ、照度:330mW/cm2、積算光量:3000mJ/cm2]後、暗室下23℃50%RHの環境下において、24時間養生の後、硬化物を取り出し、硬化物の硬化厚みを測定した。
UV照射が不要な硬化性組成物(比較例4〜5)は、直径20mm、高さ7mmの円筒形容器(ポリプロピレン)に厚みが7mmになるように硬化性組成物を注ぎ、23℃50%RHの環境下において、24時間養生の後、硬化物を取り出し、硬化物の硬化厚みを測定した。
Claims (10)
- (A)架橋性珪素基含有有機重合体と、
(B)光塩基発生剤と、
(C)Si−F結合を有するケイ素化合物と、
を含有することを特徴とする光硬化性組成物。 - (D)活性エネルギー線開裂型ラジカル発生剤をさらに含有することを特徴とする請求項1記載の光硬化性組成物
- 前記(B)光塩基発生剤が、光潜在性第3級アミンであることを特徴とする請求項1又は2記載の光硬化性組成物。
- 前記(A)架橋性珪素基含有有機重合体が、1分子中に平均して0.8個以上の架橋性珪素基を含有するポリオキシアルキレン系重合体、1分子中に平均して0.8個以上の架橋性珪素基を含有する飽和炭化水素系重合体、及び1分子中に平均して0.8個以上の架橋性珪素基を含有する(メタ)アクリル酸エステル系重合体からなる群から選択される1種以上であることを特徴とする請求項1〜3のいずれか1項記載の光硬化性組成物。
- 塩基増殖剤をさらに含有することを特徴とする請求項1〜4のいずれか1項記載の光硬化性組成物。
- 導電性フィラーをさらに含有することを特徴とする請求項1〜5のいずれか1項記載の光硬化性組成物。
- 請求項1〜6のいずれか1項記載の光硬化性組成物に対し、光を照射することにより硬化物を形成することを特徴とする硬化物の製造方法。
- 請求項1〜6のいずれか1項記載の光硬化性組成物を用いて製造することを特徴とする製品の製造方法。
- 請求項1〜6のいずれか1項記載の光硬化性組成物を接着剤として用いてなる製品。
- 請求項1〜6のいずれか1項記載の光硬化性組成物をコーティング剤として用いてなる製品。
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