JPWO2018181421A1 - 硬化性組成物および構造物 - Google Patents
硬化性組成物および構造物 Download PDFInfo
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- JPWO2018181421A1 JPWO2018181421A1 JP2019509943A JP2019509943A JPWO2018181421A1 JP WO2018181421 A1 JPWO2018181421 A1 JP WO2018181421A1 JP 2019509943 A JP2019509943 A JP 2019509943A JP 2019509943 A JP2019509943 A JP 2019509943A JP WO2018181421 A1 JPWO2018181421 A1 JP WO2018181421A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 66
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 29
- 229920006295 polythiol Polymers 0.000 claims abstract description 25
- -1 3-mercaptopropionyloxy Chemical group 0.000 claims description 107
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 39
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- 239000003795 chemical substances by application Substances 0.000 claims description 15
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- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 claims description 10
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 claims description 10
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims description 9
- HNHFTARXTMQRCF-UHFFFAOYSA-N 1,3,5-tris(3-sulfanylpropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound SCCCN1C(=O)N(CCCS)C(=O)N(CCCS)C1=O HNHFTARXTMQRCF-UHFFFAOYSA-N 0.000 claims description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 7
- YAAUVJUJVBJRSQ-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2-[[3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propoxy]methyl]-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS YAAUVJUJVBJRSQ-UHFFFAOYSA-N 0.000 claims description 6
- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 claims description 3
- QSOFJLDXOMMNNK-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpropane-1,3-diol 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O.CC(S)CC(O)=O.CC(S)CC(O)=O.OCC(C)(CO)CO QSOFJLDXOMMNNK-UHFFFAOYSA-N 0.000 claims description 3
- WBEKRAXYEBAHQF-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O.CC(S)CC(O)=O.CC(S)CC(O)=O.CCC(CO)(CO)CO WBEKRAXYEBAHQF-UHFFFAOYSA-N 0.000 claims description 3
- LABQKWYHWCYABU-UHFFFAOYSA-N 4-(3-sulfanylbutanoyloxy)butyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCCCCOC(=O)CC(C)S LABQKWYHWCYABU-UHFFFAOYSA-N 0.000 claims description 3
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 claims description 3
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 3
- IFVYLGBXAXTHSC-UHFFFAOYSA-N 3-(3-sulfanylpropoxy)propane-1-thiol Chemical compound SCCCOCCCS IFVYLGBXAXTHSC-UHFFFAOYSA-N 0.000 claims description 2
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- 238000006116 polymerization reaction Methods 0.000 description 14
- 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 13
- 150000002148 esters Chemical class 0.000 description 13
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 10
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- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 8
- 229940105570 ornex Drugs 0.000 description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 8
- 238000013007 heat curing Methods 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000007973 cyanuric acids Chemical class 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 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 6
- 238000000016 photochemical curing Methods 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 6
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 5
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- 238000005259 measurement Methods 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000001302 tertiary amino group Chemical group 0.000 description 5
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
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- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- AZLXEMARTGQBEN-UHFFFAOYSA-N trinonyl borate Chemical compound CCCCCCCCCOB(OCCCCCCCCC)OCCCCCCCCC AZLXEMARTGQBEN-UHFFFAOYSA-N 0.000 description 1
- GZKLCETYSGSMRA-UHFFFAOYSA-N trioctadecyl borate Chemical compound CCCCCCCCCCCCCCCCCCOB(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC GZKLCETYSGSMRA-UHFFFAOYSA-N 0.000 description 1
- DTBRTYHFHGNZFX-UHFFFAOYSA-N trioctyl borate Chemical compound CCCCCCCCOB(OCCCCCCCC)OCCCCCCCC DTBRTYHFHGNZFX-UHFFFAOYSA-N 0.000 description 1
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- DLVYHYUFIXLWKV-UHFFFAOYSA-N tris(2-ethylhexyl) borate Chemical compound CCCCC(CC)COB(OCC(CC)CCCC)OCC(CC)CCCC DLVYHYUFIXLWKV-UHFFFAOYSA-N 0.000 description 1
- RTMBXAOPKJNOGZ-UHFFFAOYSA-N tris(2-methylphenyl) borate Chemical compound CC1=CC=CC=C1OB(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C RTMBXAOPKJNOGZ-UHFFFAOYSA-N 0.000 description 1
- FYAMVEZOQXNCIE-UHFFFAOYSA-N tris(3-methylphenyl) borate Chemical compound CC1=CC=CC(OB(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 FYAMVEZOQXNCIE-UHFFFAOYSA-N 0.000 description 1
- RQNVJDSEWRGEQR-UHFFFAOYSA-N tris(prop-2-enyl) borate Chemical compound C=CCOB(OCC=C)OCC=C RQNVJDSEWRGEQR-UHFFFAOYSA-N 0.000 description 1
- WAXLMVCEFHKADZ-UHFFFAOYSA-N tris-decyl borate Chemical compound CCCCCCCCCCOB(OCCCCCCCCCC)OCCCCCCCCCC WAXLMVCEFHKADZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- DIHAURBCYGTGCV-UHFFFAOYSA-N xi-4,5-Dihydro-2,4(5)-dimethyl-1H-imidazole Chemical compound CC1CN=C(C)N1 DIHAURBCYGTGCV-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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Abstract
Description
(1)(メタ)アクリロイル基を有する化合物、
(2)1分子中に2個以上のメルカプト基を有するポリチオール化合物、
(3)光ラジカル発生剤、および
(4)潜在性硬化剤
を含む硬化性組成物。
[2] 成分(1)が、以下の成分(1−1):
(1−1)(メタ)アクリロイル基およびエポキシ基を有する化合物
を含む前記[1]に記載の硬化性組成物。
[3] 成分(1)が、以下の成分(1−2):
(1−2)リン酸変性(メタ)アクリレート
を含む前記[1]または[2]に記載の硬化性組成物。
[4] 成分(1)が、以下の成分(1−1)〜(1−3):
(1−1)(メタ)アクリロイル基およびエポキシ基を有する化合物、
(1−2)リン酸変性(メタ)アクリレート、および
(1−3)成分(1−1)および成分(1−2)のいずれにも該当しない(メタ)アクリロイル基を有する化合物
を含む前記[1]〜[3]のいずれか一つに記載の硬化性組成物。
[5] 成分(2)が、1分子中に2〜6個のメルカプト基を有するポリチオール化合物を含む前記[1]〜[4]のいずれか一つに記載の硬化性組成物。
[6] 成分(2)が、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)、ペンタエリスリトール テトラキス(3−メルカプトブチレート)、トリス(3−メルカプトプロピル)イソシアヌレート、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)、ジペンタエリスリトール ヘキサキス(3−メルカプトプロピオネート)、トリス[(3−メルカプトプロピオニルオキシ)エチル]イソシアヌレート、エチレングリコール ビス(メルカプトアセテート)、トリメチロールプロパン トリス(メルカプトアセテート)、ペンタエリスリトール テトラキス(メルカプトアセテート)、1,4−ビス(3−メルカプトブチリルオキシ)ブタン、1,3,5−トリス(3−メルカプトブチリルオキシエチル)−1,3,5−トリアジン−2,4,6(1H,3H,5H)−トリオン、トリメチロールプロパン トリス(3−メルカプトブチレート)、トリメチロールエタン トリス(3−メルカプトブチレート)、1,3,4,6−テトラキス(2−メルカプトエチル)グリコールウリル、および4,4’−イソプロピリデンジフェニル ビス(3−メルカプトプロピル) エーテルからなる群から選ばれる少なくとも一つを含む前記[1]〜[5]のいずれか一つに記載の硬化性組成物。
[7] 成分(2)が、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)、ペンタエリスリトール テトラキス(3−メルカプトブチレート)、トリス(3−メルカプトプロピル)イソシアヌレート、およびジペンタエリスリトール ヘキサキス(3−メルカプトプロピオネート)からなる群から選ばれる少なくとも一つを含む前記[1]〜[5]のいずれか一つに記載の硬化性組成物。
[8] 成分(1)中のアクリロイル基、メタクリロイル基およびエポキシ基の合計と成分(2)中のメルカプト基とのモル比(成分(1)中のアクリロイル基、メタクリロイル基およびエポキシ基の合計/成分(2)中のメルカプト基)が、0.5〜2.0である前記[1]〜[7]のいずれか一つに記載の硬化性組成物。
[9] 成分(4)が、アミン−エポキシアダクト系化合物およびアミン−イソシアネートアダクト系化合物からなる群から選ばれる少なくとも一つを含む前記[1]〜[8]のいずれか一つに記載の硬化性組成物。
[10] 成分(5)として、熱ラジカル発生剤をさらに含む前記[1]〜[9]のいずれか一つに記載の硬化性組成物。
[11] 第一の被着体と、第二の被着体と、これらの接着層とを含む構造物であって、
第一の被着体が、ポリカーボネート製の部材であり、
接着層が、前記[1]〜[10]のいずれか一つに記載の硬化性組成物の硬化物である構造物。
[12] カメラモジュールである前記[11]に記載の構造物。
(1)(メタ)アクリロイル基を有する化合物、
(2)1分子中にメルカプト基(−SH)を2個以上有するポリチオール化合物(以下「ポリチオール化合物」と略称することがある。)、
(3)光ラジカル発生剤、および
(4)潜在性硬化剤
を含むことを特徴とする。以下、各成分を順に説明する。
本発明において、成分(1)の「(メタ)アクリロイル基を有する化合物」は、主に接着強度を高める役割を担う成分である。本発明において「(メタ)アクリロイル基」とは、「アクリロイル基および/またはメタクリロイル基」を意味する。成分(1)は、1種のみでもよく、2種以上でもよい。
β−カルボキシエチル(メタ)アクリレート
イソボルニル(メタ)アクリレート
オクチル/デシル(メタ)アクリレート
エトキシ化フェニル(メタ)アクリレート
エポキシ基を有する(メタ)アクリレート
リン酸変性(メタ)アクリレート
EO変性フェノール (メタ)アクリレート
EO変性o−フェニルフェノール (メタ)アクリレート
EO変性パラクミルフェノール (メタ)アクリレート
EO変性ノニルフェノール (メタ)アクリレート
PO変性ノニルフェノール (メタ)アクリレート
N−(メタ)アクリロイルオキシエチルヘキサヒドロフタルイミド
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
フタル酸モノヒドロキシエチル(メタ)アクリレート
2−ヒドロキシ−3−フェノキシプロピル(メタ)アクリレート
ジプロピレングリコール 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
トリプロピレングリコール ジ(メタ)アクリレート
PO変性ネオペンチルグリコール ジ(メタ)アクリレート
トリシクロデカンジメタノール ジ(メタ)アクリレート
EO変性ビスフェノールF ジ(メタ)アクリレート
EO変性ビスフェノールA ジ(メタ)アクリレート
EO変性イソシアヌル酸 ジ(メタ)アクリレート
ポリプロピレングリコール 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
ネオペンチルグリコール ヒドロキシピバリン酸エステル ジ(メタ)アクリレート
1分子中に2個の(メタ)アクリロイル基を有するポリウレタン
1分子中に2個の(メタ)アクリロイル基を有するポリエステル
トリメチロールプロパン トリ(メタ)アクリレート
PO変性トリメチロールプロパン トリ(メタ)アクリレート
EO変性トリメチロールプロパン トリ(メタ)アクリレート
EO変性イソシアヌル酸 (トリ)(メタ)アクリレート
ペンタエリスリトール (トリ/テトラ)(メタ)アクリレート
グリセリン プロポキシトリ(メタ)アクリレート
ペンタエリスリトール エトキシ テトラ(メタ)アクリレート
ジトリメチロールプロパン テトラ(メタ)アクリレート
ジペンタエリスリトール (ペンタ/ヘキサ)(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
EO変性ジグリセリン テトラ(メタ)アクリレート
1分子中に3個以上の(メタ)アクリロイル基を有するポリウレタン
1分子中に3個以上の(メタ)アクリロイル基を有するポリエステル
(i)1分子中に2個以上のエポキシ基を有するエポキシ化合物と、(メタ)アクリル酸とを、前記エポキシ化合物のエポキシ基が残るような量比で反応させる方法。
なお、本発明において「(メタ)アクリル酸」とは、「アクリル酸および/またはメタクリル酸」を意味する。
(ii)(メタ)アクリロイル基およびヒドロキシ基を有する化合物とリン酸とを反応させる方法。
(iii)(メタ)アクリル酸または(メタ)アクリレートと、多価アルコール(例えば、アルキレングリコール、グリセリン等)とを、前記多価アルコールのヒドロキシ基が残るような量比で反応させる方法。
(iv)(メタ)アクリル酸にアルキレンオキシド(例えば、エチレンオキシド、プロピレンオキシド等)を付加させる方法。
本発明の硬化性組成物において、成分(2)の「1分子中に2個以上のメルカプト基を有するポリチオール化合物」は、主として、紫外線等の光照射により成分(1)を硬化させる硬化剤の役割を担う。成分(2)は、1種のみでもよく、2種以上でもよい。ポリチオール化合物の1分子中のメルカプト基の数は、好ましくは2〜6、より好ましくは3〜6、さらに好ましくは3〜5、特に好ましくは3または4である。
本発明において光ラジカル発生剤に特に限定はないが、例えば、アルキルフェノン系光ラジカル発生剤、アシルホスフィンオキサイド系光ラジカル発生剤、オキシムエステル系光ラジカル発生剤、α−ケトン系光ラジカル発生剤等が挙げられる。成分(3)は、1種のみでもよく、2種以上でもよい。光ラジカル発生剤は、好ましくはアルキルフェノン系光ラジカル発生剤である。
成分(4)の潜在性硬化剤とは、エポキシ樹脂等の分野で周知の添加剤であって、常温(25℃)ではエポキシ樹脂等を硬化させないが、加熱することによってエポキシ樹脂等を硬化させ得る硬化剤を意味する。成分(4)は、1種のみでもよく、2種以上でもよい。
本発明の硬化性組成物は、成分(5)として、熱ラジカル発生剤をさらに含有していてもよい。成分(5)は、1種のみでもよく、2種以上でもよい。熱ラジカル発生剤としては、例えば、アゾ化合物、有機過酸化物等が挙げられる。
本発明の効果を損なわない範囲で、本発明の硬化性組成物は、上記成分(1)〜(5)とは異なる他の成分を含有していてもよい。他の成分としては、例えば、重合禁止剤(例えば、ジブチルヒドロキシトルエン、バルビツール酸);酸化防止剤;無機フィラー(例えば、炭酸カルシウム、炭酸マグネシウム、硫酸バリウム、硫酸マグネシウム、珪酸アルミニウム、珪酸ジルコニウム、酸化鉄、酸化チタン、酸化アルミニウム(アルミナ)、酸化亜鉛、二酸化珪素、チタン酸カリウム、カオリン、タルク、石英粉等);ポリメタクリル酸メチルおよび/またはポリスチレンにこれらを構成するモノマーと共重合可能なモノマーとを共重合させた共重合体等からなる有機フィラー;チキソ剤;消泡剤;レベリング剤;カップリング剤;難燃剤;顔料;染料;蛍光剤等が挙げられる。他の成分は、いずれも、1種でもよく、2種以上でもよい。
本発明の硬化性組成物を製造することには特別の困難はない。例えば、ニーダー、攪拌混合機、三本ロールミル等を用いて、各成分を均一に混合することによって、一液型の硬化性組成物として調製することができる。混合の際の硬化性組成物の温度は、通常10〜40℃、好ましくは20〜30℃である。
本発明の硬化性組成物は、優れた光硬化性と優れた熱硬化性を併せ持ち、高い接着強度を有する硬化物を形成し得る。従って、本発明の硬化性組成物の用途としては、接着剤、封止剤、コーティング剤等を挙げることができる。これらの用途の中でも、接着剤が好ましい。
本発明は、第一の被着体と、第二の被着体と、これらの接着層とを含む構造物であって、第一の被着体が、ポリカーボネート製の部材であり、接着層が、上述した本発明の硬化性組成物の硬化物である構造物を提供する。なお、本発明の構造物では、第一の被着体と第二の被着体とが、接着層を介して接合される。第一の被着体であるポリカーボネート製の部材としては、例えばレンズ、レンズホルダー、ハウジング等が挙げられる。本発明の構造物は、好ましくはスマートフォンなどの携帯機器に搭載されるカメラモジュールである。
(I)本発明の硬化性組成物を、センサーケースに塗布し、この硬化性組成物が塗布されたセンサーケースと、ハウジングとを位置決めする工程。
(II)光照射により硬化性組成物を硬化(予備硬化)させて第一の被着体および第二の被着体を仮固定する工程。
(III)加熱により硬化性組成物を硬化(本硬化)させて、接着層(即ち、硬化性組成物の硬化物)を形成し、第一の被着体および第二の被着体を本固定する工程。
<(1)(メタ)アクリロイル基を有する化合物>
(1A)UVACURE 1561:ダイセル・オルネクス株式会社製、エポキシ樹脂ハーフアクリレート(アクリロイル基およびエポキシ基を有する化合物)、エポキシ当量:450g/eq、分子量:450、1分子中のアクリロイル基の数:1、1分子中のエポキシ基の数:1
(1B)IRR−214K:ダイセル・オルネクス株式会社製、トリシクロデカンジメタノール ジアクリレート、分子量:300、1分子中のアクリロイル基の数:2
(1C)EBECRYL150:ダイセル・オルネクス株式会社製、EO変性ビスフェノールA ジアクリレート、分子量:512、1分子中のアクリロイル基の数:2
(1D)DPHA:ダイセル・オルネクス株式会社製、ジペンタエリスリトール ヘキサアクリレート、分子量:524、1分子中のアクリロイル基の数:6
(1E)EBECRYL810:ダイセル・オルネクス株式会社製、ポリエステルアクリレート(アクリロイル基を有するポリエステル)、分子量:1,000、1分子中のアクリロイル基の数:4
(1F)EBECRYL168:ダイセル・オルネクス株式会社製、リン酸変性メタクリレート、1分子中のメタクリロイル基の数:1.5
(1G)KAYAMER PM−2:日本化薬株式会社製、リン酸変性メタクリレート、分子量:259、1分子中のメタクリロイル基の数:1.5
(1H)KAYAMER PM−21:日本化薬株式会社製、リン酸変性メタクリレート、分子量:437、1分子中のメタクリロイル基の数:1.5
(2A)PEMP:SC有機化学株式会社製、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)、分子量:489、1分子中のメルカプト基の数:4
(2B)PE−1:昭和電工株式会社製「カレンズMT PE−1」、ペンタエリスリトール テトラキス(3−メルカプトブチレート)、分子量:544、1分子中のメルカプト基の数:4
(2C)TMPIC:トリス(3−メルカプトプロピル)イソシアヌレート、分子量:351、1分子中のメルカプト基の数:3
(2D)DPMP:淀化学工業株式会社製、ジペンタエリスリトール ヘキサキス(3−メルカプトプロピオネート)、分子量:783、1分子中のメルカプト基の数:6
(3A)IRGACURE 1173:BASF社製、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン
(3B)ESACURE KIP 150:Lamberti SPA社製、2−ヒドロキシ−1−(4−イソプロペニルフェニル)−2−メチルプロパン−1−オンのオリゴマー
(4A)PN−23:味の素ファインテクノ株式会社製、アミン−エポキシアダクト系化合物
(4B)FXR1081:株式会社T&K TOKA製、アミン−イソシアネートアダクト系化合物
(5A)V−601:和光純薬工業株式会社製、ジメチル 2,2’−アゾビス(2−メチルプロピオネート)、10時間半減期温度:66℃
(5B)パーオクタO:日油株式会社製、1,1,3,3−テトラメチルブチルパーオキシ−2−エチルヘキサノエート、10時間半減期温度;65.3℃
(6A)Q−1301:和光純薬工業株式会社製、N−ニトロソ−N−フェニルヒドロキシアミンアルミニウム塩
(6B)トリエチルボレート:純正化学工業株式会社製
(6C)バルビツール酸:東京化成株式会社製
[熱硬化性の評価]
幅2.5mm×長さ8.0mm×厚さ0.8mmのガラスエポキシ樹脂積層板(利昌工業社製、FR−4.0)に厚さ:約50μmのスペーサーを使って、硬化性組成物をバーコーターによって塗布して、硬化性組成物の塗膜を形成し、これを熱風循環オーブンにて80℃で60分間加熱して硬化させ、以下の基準の指触による塗膜外観観察にて、熱硬化性を評価した。
<評価基準>
○:未硬化成分なし
△:多少ベタつきあり
×:未硬化
(1)光硬化後の接着強度1の測定
幅25mm×長さ100mm×厚さ2.0mmのポリカーボネート板(三菱エンジニアリングプラスチックス株式会社製、ユーピロンNF−2000)を80℃で20分プレ乾燥し、室温まで冷却した後、ポリカーボネート上に硬化性組成物を1〜3mgの量で塗布し、その上にコンデンサーチップ(JIS呼称:2012サイズ)を乗せ、下記の条件にて光硬化を行い、硬化物の接着強度1を測定し、下記基準で評価した。
(2)光および熱硬化後の接着強度2の測定
上記と同様に、プレ乾燥を行ったポリカーボネート板への硬化性組成物の塗布、コンデンサーチップの載置を行ったものに対し、下記の条件にて光および熱硬化を行い、硬化物の接着強度2を測定し、下記基準で評価した。
(3)熱硬化後の接着強度3の測定
上記と同様に、プレ乾燥を行ったポリカーボネート板へ硬化性組成物の塗布、コンデンサーチップの載置を行ったものに対し、下記の条件にて熱硬化を行い、硬化物の接着強度3を測定し、下記基準で評価した。
(1)光硬化
パナソニック社製UV―LED照射装置UJ35により、照度2,500mW/cm2の紫外線(ピーク波長:365nm)を、二方向から角度45°(コンデンサーチップ表面への光の入射角度が45°)で、硬化性組成物に1.2秒間照射した(露光量3,000mJ/cm2)。
(2)光および熱硬化
パナソニック社製UV―LED照射装置UJ35により、照度2,500mW/cm2の紫外線(ピーク波長:365nm)を、二方向から角度45°(コンデンサーチップ表面への光の入射角度が45°)で、硬化性組成物に1.2秒間照射した(露光量3,000mJ/cm2)。次いで、光照射した硬化性組成物を熱循環式オーブンにて80℃で60分間加熱した。
(3)熱硬化
硬化性組成物を、熱循環式オーブンにて80℃で60分加熱した。
(1)光硬化後の接着強度1の評価基準
○:5N/mm2以上
△:2〜5N/mm2未満
×:2N/mm2未満
(2)光および熱硬化後の接着強度2の評価基準
○:10N/mm2以上
△:5〜10N/mm2未満
×:5N/mm2未満
(3)熱硬化後の接着強度3の評価基準
○:10N/mm2以上
△:5〜10N/mm2未満
×:5N/mm2未満
上述の熱硬化後の接着強度3を測定した後の接着箇所のポリカーボネートの状態をデジタルマイクロスコープ(キーエンス社製、VHX−2000、倍率:250倍)にて観察した。接着箇所全体に対するボイドの割合(面積%)を測定し、下記基準により評価した。
<評価基準>
○:ボイドの量が5面積%未満
△:ボイドの量が5〜10面積%未満
×:ボイドの量が10面積%以上
硬化性組成物をプラスティック製密閉容器に25℃にて保管し、ゲル化するまでの日数を確認し、下記基準により評価した。
<評価基準>
○:7日以上
△:3〜6日
×:3日未満
下記表1〜3に示す量で各成分を混合して、実施例1〜15および比較例1〜4の硬化性組成物を調製した。表中の各成分の数字は配合量(重量部)を示す。また、下記表1〜3には、「成分(1)中のアクリロイル基、メタクリロイル基およびエポキシ基の合計と成分(2)中のメルカプト基とのモル比」を「((メタ)アクリロイル基+エポキシ基)/メルカプト基」の欄に記載する。
Claims (12)
- 以下の成分(1)〜(4):
(1)(メタ)アクリロイル基を有する化合物、
(2)1分子中に2個以上のメルカプト基を有するポリチオール化合物、
(3)光ラジカル発生剤、および
(4)潜在性硬化剤
を含む硬化性組成物。 - 成分(1)が、以下の成分(1−1):
(1−1)(メタ)アクリロイル基およびエポキシ基を有する化合物
を含む請求項1に記載の硬化性組成物。 - 成分(1)が、以下の成分(1−2):
(1−2)リン酸変性(メタ)アクリレート
を含む請求項1または2に記載の硬化性組成物。 - 成分(1)が、以下の成分(1−1)〜(1−3):
(1−1)(メタ)アクリロイル基およびエポキシ基を有する化合物、
(1−2)リン酸変性(メタ)アクリレート、および
(1−3)成分(1−1)および成分(1−2)のいずれにも該当しない(メタ)アクリロイル基を有する化合物
を含む請求項1〜3のいずれか一項に記載の硬化性組成物。 - 成分(2)が、1分子中に2〜6個のメルカプト基を有するポリチオール化合物を含む請求項1〜4のいずれか一項に記載の硬化性組成物。
- 成分(2)が、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)、ペンタエリスリトール テトラキス(3−メルカプトブチレート)、トリス(3−メルカプトプロピル)イソシアヌレート、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)、ジペンタエリスリトール ヘキサキス(3−メルカプトプロピオネート)、トリス[(3−メルカプトプロピオニルオキシ)エチル]イソシアヌレート、エチレングリコール ビス(メルカプトアセテート)、トリメチロールプロパン トリス(メルカプトアセテート)、ペンタエリスリトール テトラキス(メルカプトアセテート)、1,4−ビス(3−メルカプトブチリルオキシ)ブタン、1,3,5−トリス(3−メルカプトブチリルオキシエチル)−1,3,5−トリアジン−2,4,6(1H,3H,5H)−トリオン、トリメチロールプロパン トリス(3−メルカプトブチレート)、トリメチロールエタン トリス(3−メルカプトブチレート)、1,3,4,6−テトラキス(2−メルカプトエチル)グリコールウリル、および4,4’−イソプロピリデンジフェニル ビス(3−メルカプトプロピル) エーテルからなる群から選ばれる少なくとも一つを含む請求項1〜5のいずれか一項に記載の硬化性組成物。
- 成分(2)が、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)、ペンタエリスリトール テトラキス(3−メルカプトブチレート)、トリス(3−メルカプトプロピル)イソシアヌレート、およびジペンタエリスリトール ヘキサキス(3−メルカプトプロピオネート)からなる群から選ばれる少なくとも一つを含む請求項1〜5のいずれか一項に記載の硬化性組成物。
- 成分(1)中のアクリロイル基、メタクリロイル基およびエポキシ基の合計と成分(2)中のメルカプト基とのモル比(成分(1)中のアクリロイル基、メタクリロイル基およびエポキシ基の合計/成分(2)中のメルカプト基)が、0.5〜2.0である請求項1〜7のいずれか一項に記載の硬化性組成物。
- 成分(4)が、アミン−エポキシアダクト系化合物およびアミン−イソシアネートアダクト系化合物からなる群から選ばれる少なくとも一つを含む請求項1〜8のいずれか一項に記載の硬化性組成物。
- 成分(5)として、熱ラジカル発生剤をさらに含む請求項1〜9のいずれか一項に記載の硬化性組成物。
- 第一の被着体と、第二の被着体と、これらの接着層とを含む構造物であって、
第一の被着体が、ポリカーボネート製の部材であり、
接着層が、請求項1〜10のいずれか一項に記載の硬化性組成物の硬化物である構造物。 - カメラモジュールである請求項11に記載の構造物。
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CN110431168B (zh) | 2022-04-29 |
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