WO2014132464A1 - ラジカル、アニオン併用型光硬化材料 - Google Patents
ラジカル、アニオン併用型光硬化材料 Download PDFInfo
- Publication number
- WO2014132464A1 WO2014132464A1 PCT/JP2013/071652 JP2013071652W WO2014132464A1 WO 2014132464 A1 WO2014132464 A1 WO 2014132464A1 JP 2013071652 W JP2013071652 W JP 2013071652W WO 2014132464 A1 WO2014132464 A1 WO 2014132464A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acrylate
- meth
- curing
- light
- chain transfer
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 64
- 125000000129 anionic group Chemical group 0.000 title abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 99
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 38
- 239000007788 liquid Substances 0.000 claims abstract description 34
- 125000005370 alkoxysilyl group Chemical group 0.000 claims abstract description 26
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 239000004202 carbamide Substances 0.000 claims abstract description 10
- 238000000016 photochemical curing Methods 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- 239000011135 tin Substances 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 238000001723 curing Methods 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 43
- -1 hydrogen compound Chemical class 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
- 239000012948 isocyanate Substances 0.000 description 18
- 150000001450 anions Chemical class 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 12
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 11
- 239000004814 polyurethane Substances 0.000 description 11
- 229920002635 polyurethane Polymers 0.000 description 11
- 150000002009 diols Chemical class 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000013008 moisture curing Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000004985 diamines Chemical group 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 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 5
- 238000011156 evaluation Methods 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000011417 postcuring Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- VKLXPBBZKVZDLB-UHFFFAOYSA-N 2-hydroxyethyl carbamodithioate Chemical compound NC(=S)SCCO VKLXPBBZKVZDLB-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 208000034189 Sclerosis Diseases 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
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- 239000000049 pigment Substances 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
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- 239000003566 sealing material Substances 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- CYDXJXDAFPJUQE-SYWGCQIGSA-L zinc;(e)-4-oxopent-2-en-2-olate Chemical compound [Zn+2].C\C([O-])=C/C(C)=O.C\C([O-])=C/C(C)=O CYDXJXDAFPJUQE-SYWGCQIGSA-L 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- KFDRXQXGGQXFNP-DERJAXIWSA-J (z)-1,2-dicyanoethene-1,2-dithiolate;nickel(2+);tetrabutylazanium Chemical compound [Ni+2].N#CC(/[S-])=C(/[S-])C#N.N#CC(/[S-])=C(/[S-])C#N.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC KFDRXQXGGQXFNP-DERJAXIWSA-J 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- HSKPJQYAHCKJQC-UHFFFAOYSA-N 1-ethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC HSKPJQYAHCKJQC-UHFFFAOYSA-N 0.000 description 1
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- XANIFASCQKHXRC-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2s1.Oc1ccccc1-c1nc2ccccc2s1 XANIFASCQKHXRC-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- YPGYFPCHCFXUKD-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propoxy]propoxy]propoxy]propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(=O)C=C YPGYFPCHCFXUKD-UHFFFAOYSA-N 0.000 description 1
- YCPMSWJCWKUXRH-UHFFFAOYSA-N 2-[4-[9-[4-(2-prop-2-enoyloxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethyl prop-2-enoate Chemical compound C1=CC(OCCOC(=O)C=C)=CC=C1C1(C=2C=CC(OCCOC(=O)C=C)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YCPMSWJCWKUXRH-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- VVOPUZNLRVJDJQ-UHFFFAOYSA-N phthalocyanine copper Chemical compound [Cu].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 VVOPUZNLRVJDJQ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- LLVONELOQJAYBZ-UHFFFAOYSA-N tin(ii) phthalocyanine Chemical compound N1=C(C2=CC=CC=C2C2=NC=3C4=CC=CC=C4C(=N4)N=3)N2[Sn]N2C4=C(C=CC=C3)C3=C2N=C2C3=CC=CC=C3C1=N2 LLVONELOQJAYBZ-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- IEKWPPTXWFKANS-UHFFFAOYSA-K trichlorocobalt Chemical compound Cl[Co](Cl)Cl IEKWPPTXWFKANS-UHFFFAOYSA-K 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JGOIIPRSFZFFHG-UHFFFAOYSA-N trimethyl(2-tributylstannylethynyl)silane Chemical compound CCCC[Sn](CCCC)(CCCC)C#C[Si](C)(C)C JGOIIPRSFZFFHG-UHFFFAOYSA-N 0.000 description 1
- HDWHGDDNMJOCCU-UHFFFAOYSA-N trimethyl(pyridin-2-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=CC=N1 HDWHGDDNMJOCCU-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- AUMBZPPBWALQRO-UHFFFAOYSA-L zinc;n,n-dibenzylcarbamodithioate Chemical compound [Zn+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 AUMBZPPBWALQRO-UHFFFAOYSA-L 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/831—Chemically modified polymers by oxygen-containing compounds inclusive of carbonic acid halogenides, carboxylic acid halogenides and epoxy halides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/837—Chemically modified polymers by silicon containing compounds
Definitions
- the present invention relates to a photo-curing material using both radical curable and anion curable, and more specifically, an adhesive material, a coating material, a sealing material, a mold, such as an automobile, an electric / electronic device, and an aircraft member.
- the present invention relates to a photo-curing material used for a molding material or the like.
- adhesives and paints use a method in which pigments and resins are dissolved in organic solvents and water, applied to the target material in a liquid state, and a cured product is obtained by volatilizing the organic solvent and water.
- organic solvents and water there are many.
- an organic solvent there is a problem of health effects and flammability due to volatile gas, and in the case of water, there is a problem that it takes time to obtain a cured product due to low volatility.
- the photocuring material is used as a useful material because the liquid composition can be cured only by light irradiation. Since the photo-curing material is usually cured only at a portion irradiated with light, it is difficult to cure a portion that is difficult for light to reach. Accordingly, various chain transfer agents are used as additives in order to enable curing to a place (dark part) that is a certain distance or more from the light irradiation part (see, for example, Patent Document 1).
- the ultraviolet curable composition described in Patent Document 1 is a combination of an ultraviolet curable material composed of (meth) acrylate and a photopolymerization initiator and a chain transfer agent.
- the chain transfer agent comprises a reaction between a polypropylene glycol having a molecular weight of 400 and hexamethylene diisocyanate in an excess number of moles, further reacting with the remaining isocyanate group to terminate the acrylate group at the end, and a metal-containing compound. What was blended can be mentioned (see Examples in Patent Document 1).
- the problem to be solved by the present invention is to provide a photo-curing material which can be cured in a dark part even if the form of the material to be cured is complicated and the distance of the non-irradiated part becomes long.
- the photo-curing material of the present invention comprises: A photocurable liquid composition that can be cured by light irradiation, Contains (meth) acrylate and chain transfer agent,
- the gist is that the chain transfer agent is a compound containing at least one selected from a urethane bond, a urea bond, or an isocyanate group and one or more alkoxysilyl groups.
- the photocurable material further contains a metal-containing compound.
- the content of the chain transfer agent is preferably in the range of 10 to 90% by mass of the entire photocurable material.
- the metal-containing compound is preferably a metal compound of tin, copper, zinc, cobalt, or nickel.
- the curable material of the present invention is a photocurable liquid composition that can be cured by light irradiation, and contains (meth) acrylate and a chain transfer agent, and the chain transfer agent is a urethane bond, a urea bond, or an isocyanate. Since at least one selected from the group is a compound containing one or more and one or more alkoxysilyl groups, it has both radical curable and anionic curable properties, and can be cured to a site that does not reach irradiation light. It is possible, and even if the form of the material to be cured is complicated and the distance of the non-irradiated part becomes long, the dark part can be cured.
- the photo-curing material of the present invention comprises a liquid composition having both a curability of radical curing in which radicals are involved and radical curing in which anions are involved by irradiation with light such as ultraviolet rays.
- the photo-curing material contains at least a (meth) acrylate component and a chain transfer agent component.
- visible light, infrared rays, etc. are contained in addition to an ultraviolet-ray with the light used for hardening of a photocurable material by this invention.
- the liquid state of the photocuring material means that it has fluidity at room temperature. From the viewpoint of good fluidity, the viscosity of the cured material is preferably in the range of 0.01 to 50 Pa ⁇ s.
- (meth) acrylate means that both acrylate and methacrylate are included.
- the general curing principle of ultraviolet curable resins is that the photopolymerization initiator absorbs ultraviolet rays (ultraviolet light) to generate active species such as radical species, and the active species is carbon-carbon such as (meth) acrylate. These double bonds are radically polymerized and cured. However, in the ultraviolet curable resin, the portion where the ultraviolet rays are shielded becomes uncured by ordinary ultraviolet curing. On the other hand, by adding a chain transfer agent to the curable material, the radicals generated by the irradiation of ultraviolet rays are transmitted to a place where the ultraviolet rays are shielded and no radicals are generated, and the polymerization reaction is started and advanced. Dark part sclerosis
- the present invention is greatly characterized in that a compound containing at least one selected from a urethane bond, a urea bond, or an isocyanate group and a compound containing one or more alkoxysilyl groups is used as a chain transfer agent.
- a chain transfer agent a compound containing one or more urethane bonds, urea bonds, or isocyanate groups has been used as described in Patent Document 1 above.
- an alkoxysilyl group is further introduced into a part of a compound containing one or more urethane bonds, urea bonds, or isocyanate groups, which is the above-described component of the chain transfer agent.
- an alkoxysilyl group is used as a curing reactive group of a moisture curing material in the presence of a catalyst.
- a dehydration condensation reaction further proceeds. Hydrolysis becomes a reaction that depends on the humidity of the atmosphere, and the curing rate of moisture-curing materials is generally slow.
- this curing reaction is cured through an anion (hydroxyl group) generated as a by-product, it can be called anion curing. That is, by using a chain transfer agent having a structure containing at least one selected from a urethane bond, a urea bond, or an isocyanate group and one or more alkoxysilyl groups in one molecule described above, Radical curing and anion curing occur at the same time, making it possible to cure dark areas over longer distances.
- the chain transfer agent can be obtained, for example, by the following method.
- an active hydrogen-containing compound such as polyol or polyamine is reacted with polyisocyanate to form a urethane bond or a urea bond portion.
- this reaction can be synthesized as a polymer by adjusting the ratio of the isocyanate group and the active hydrogen compound.
- an isocyanate intermediate in which an isocyanate group remains at the terminal is generated.
- this intermediate is reacted with an organosilane compound having an alkoxysilyl group and a functional group such as an amino group or a hydroxyl group at the terminal (for example, a silane coupling agent), whereby the terminal is modified with an alkoxysilyl group.
- an organosilane compound having an alkoxysilyl group and a functional group such as an amino group or a hydroxyl group at the terminal for example, a silane coupling agent
- Transfer agents can be synthesized.
- the chain transfer agent shown in Chemical Formula 1 is prepared by reacting a polyoxyalkylene diol with a diisocyanate to produce an intermediate having an isocyanate group at the end, and then further adding an amino group and an alkoxyl to the isocyanate groups at both ends of the intermediate. It is obtained by reacting an amino group of a silane coupling agent having a group.
- R is an alkyl group such as CH 3 or C 2 H 5
- X is a divalent hydrocarbon group such as C 2 H 4 , C 3 H 6 , C 4 H 8
- Y is Linear chain such as C 4 H 8 and C 6 H 12
- saturated cyclic such as cyclohexyl, dicyclohexyl, isophoronyl and norbornyl
- unsaturated cyclic divalent hydrocarbon group such as tolylene, xylylene, naphthalene and diphenylmethane
- Z is It is a repeating unit of a diol component such as polyoxypropylene glycol, polyoxyethylene glycol, polytetramethylene ether, etc.
- n is about 5 to 100
- m is about 2 to 100.
- the photoreactive property is improved.
- a chain transfer agent into which both an acryloyl group (or methacryloyl group) and an anion-reactive alkoxysilyl group are introduced can be synthesized.
- hydroxyl groups are accompanied by the cleavage of (meth) acrylate.
- One of the molecules has already been incorporated into the polymer by a photoradical reaction, and the other hydroxyl group can be further bonded to an alkoxysilyl group by a transesterification reaction, so that a condensation reaction occurs after the photoradical polymerization reaction.
- the curing reaction by moisture is a two-step reaction because the alkoxysilyl group is once hydrolyzed and transesterified with the generated silanol group as shown in the chemical formula (4). Therefore, it can be said that the reaction via the hydroxyl group is faster.
- this reaction system can be said to be a kind of anionic polymerization. Unlike the radical chain reaction, this reaction is due to the diffusion of the generated anion molecules, so the reaction speed is slower than the photoradical reaction, but it can be moved to longer distances, and the long-distance dark area hardening associated therewith. The reaction becomes possible.
- chain transfer agents examples include monoisocyanate, diisocyanate, and trifunctional or higher polyisocyanate.
- examples of the monoisocyanate include stearyl isocyanate.
- examples of the diisocyanate include methylene diisocyanate, ethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), dodecamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, lysine diisocyanate (LDI), 1,3,6-hexa.
- Aliphatic isocyanates such as methylene triisocyanate, hydrogenated-4,4′-diphenylmethane diisocyanate (hydrogenated MDI), hydrogenated-xylylene diisocyanate (hydrogenated XDI), 1,4-cyclohexane diisocyanate, hydrogenated-2,4 -Alicyclic isocyanates such as tolylene diisocyanate (hydrogenated TDI), isophorone diisocyanate (IPDI), norbornene diisocyanate (NBDI)
- Aromatic aliphatic isocyanates such as xylylene diisocyanate (XDI) and tetramethylxylylene diisocyanate (TMXDI), 1,4-diphenyl diisocyanate, 2,4 or 2,6-tolylene diisocyanate (TDI), 2, 4 or 4 , 4-diphenylmethane diisocyanate (MDI), 1,5-naphthalene di
- bifunctional polyisocyanate examples include aromatic isocyanates such as polyphenylmethane polyisocyanate (crude MDI), triphenylmethane triisocyanate, and tris (isocyanatophenyl) thiophosphate.
- aromatic isocyanates such as polyphenylmethane polyisocyanate (crude MDI), triphenylmethane triisocyanate, and tris (isocyanatophenyl) thiophosphate.
- isocyanate compound biuret type polyisocyanate obtained by further reacting the polyisocyanate with water, adduct type polyisocyanate obtained by reacting with a polyhydric alcohol such as trimethylolpropane, multimer obtained by isocyanuration Etc.
- a polyhydric alcohol such as trimethylolpropane
- multimer obtained by isocyanuration Etc multimer obtained by isocyanuration Etc.
- the isocyanate compound the above compounds may be used alone or in combination of two or more.
- Examples of the hydroxyl group-containing compound that reacts with the isocyanate compound to form a urethane bond include alcohols having 1 to 30 carbon chains having a hydroxyl group at a terminal, (poly) ethylene glycol as a terminal diol, (poly) propylene glycol as a terminal diol, (Poly) hexamethylene glycol of terminal diol, (poly) caprolactone of terminal diol, (poly) ester (poly) ol of terminal diol, (poly) amide of terminal diol, (poly) ester of terminal diol, and the like.
- Examples of the amine-containing compound that reacts with the isocyanate compound to form a urea bond include amines having 1 to 30 carbon chains having a primary or secondary amino group at the terminal, (poly) ethylene glycol as a terminal diamine, and terminal diamine. (Poly) propylene glycol, terminal diamine (poly) hexamethylene glycol, terminal diamine (poly) caprolactone, terminal diamine (poly) ester (poly) ol, terminal diamine (poly) amide, terminal diamine (poly ) Esters and the like.
- silane compound having an alkoxysilyl group and an amino group to be reacted with the isocyanate group examples include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3- (2-aminoethyl) aminopropyltrimethoxysilane, 3 -Phenylaminopropyltrimethoxysilane and the like.
- examples of the organic silane compound having an alkoxyl group and a hydroxyl group include 3-hydroxypropyltrimethoxysilane and 3-hydroxypropyltriethoxysilane.
- Examples of the hydroxyalkyl (meth) acrylate to be reacted with the isocyanate group include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxybutyl acrylate, 4-hydroxybutyl acrylate, and 1,4-cyclohexanedimethanol mono Examples include acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate and the like.
- Hydroxyalkyl (meth) acrylate is a monoacrylate containing one acryloyl group and a hydroxyl group in one molecule, a diacrylate containing two acryloyl groups and a hydroxyl group in one molecule, and three or more acryloyl groups and a hydroxyl group in one molecule. Polyacrylate or the like can be used.
- the alkyl group of the hydroxyalkyl (meth) acrylate may be linear or cyclic, for example, C 1 to C 10 , may contain an unsaturated bond, and may contain a substituent, an ether bond, or a thioether bond. It is an alkyl chain.
- the content of the chain transfer agent is preferably in the range of 10 to 90 mass of the entire photocurable material. When it is within the above range, the physical properties before and after curing are stabilized, and a sufficient chain transfer effect is obtained.
- the (meth) acrylate used for the photocuring material is not particularly limited as long as it is a compound having one or more (meth) acrylate groups in the molecule, and conventionally known ones can be used.
- Specific examples of the (meth) acrylate include isobornyl (meth) acrylate, bornyl (meth) acrylate, tricyclodecanyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, cyclohexyl ( (Meth) acrylate, (meth) acrylic acid, benzyl (meth) acrylate, 4-butylcyclohexyl (meth) acrylate, (meth) acryloylmorpholine, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4 -Hydroxybutyl (meth) acrylate, methyl (meth) acryl
- the photocurable material preferably further contains a metal-containing compound and a photopolymerization initiator.
- the content of the metal-containing compound is preferably 0.0005% by mass or more based on the entire photocurable material from the viewpoint of further improving dark portion curability.
- the form of the metal-containing compound is preferably a metal salt such as an organic acid salt or a metal complex because it is easy to mix when used as a curable material and prevents precipitation during storage.
- metal salt of the metal-containing compound examples include forms of the above metal species such as carboxylate, phosphate, sulfonate, hydrochloride, bromate, and (per) (chlorite) chlorate.
- the metal-containing compound examples include bis (2,4-pentanedionato) tin, dibutyltin bis (trifluoromethanesulfonate), dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate, phthalocyanine tin (IV) dichloride, Tetrabutylammonium difluorotriphenyltin, phthalocyanine tin (II), tributyl (2-pyridyl) tin, tributyl (2-thienyl) tin, tributyltin acetate, tributyl (trimethylsilylethynyl) tin, trimethyl (2-pyridyl) tin, bis ( Hexafluoroacetylacetonato) copper (II), bis (2,4-pentanedionato) copper (II), bis (1,3-propanediamine) copper (I
- the photopolymerization initiator added to the photocuring material is not particularly limited as long as it is a compound that absorbs ultraviolet rays and initiates radical polymerization, and conventionally known photopolymerization initiators can be used.
- the photopolymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenylacetophenone, xanthone, fluorenone, benzaldehyde, fluorene, anthraquinone, ethylanthraquinone, triphenylamine, carbazole, 3 -Methylacetophenone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, 4,4'-diaminobenzophenone, Michler's ketone, benzoin propyl ether, benzoin ethyl ether, benzyl dimethyl ketal, 1- (4-isopropylphenyl) -2- Hydroxy-2-methylpropan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, thioxanthone, diethylthioxanthone, 2-isopropyl Oxanthone, 2-
- photopolymerization initiator commercially available products such as IRGACURE184, 369, 651, 500, 907, CGI1700, CGI1750, CGI1850, CG24-61; Etc.) can be used.
- the photo-curing material may be prepared by mixing each of the above components at room temperature or under heating conditions, and is not particularly limited, but each of the above components may be mixed at an appropriate temperature under reduced pressure or an inert gas atmosphere such as nitrogen. It is preferable to use a method of sufficiently stirring or kneading using a stirring device such as a mixing mixer to dissolve or uniformly disperse.
- additives other than the above components can be contained as required.
- examples of the additive include stabilizers, softeners, pigments, dyes, antistatic agents, flame retardants, sensitizers, dispersants, solvents, antibacterial and antifungal agents.
- Each additive can be used in combination as appropriate.
- the photo-curing material of the present invention can be cured by polymerization with light such as ultraviolet rays.
- the photo-curing material can be used for an adhesive material, a coating material, a sealing material, a molding material, and the like such as an automobile member, an electric / electronic device, and an aircraft member.
- the conditions of ultraviolet irradiation when the cured material is cured with ultraviolet rays to obtain a cured product can be appropriately selected according to the composition of the cured material.
- an irradiation apparatus used for ultraviolet irradiation a known apparatus can be used.
- the irradiation device for example, a light source such as a bulb-type UV lamp or an LED-UV lamp in which Hg, Hg / Xe, a metal halide compound, or the like is sealed can be used.
- the ultraviolet irradiation device may use a condensing UV irradiation device that collects and irradiates light from the light source with a reflection mirror.
- Tables 1 and 2 show examples of preparing photocurable materials and examples
- Table 3 shows examples of preparation and comparative examples.
- the components shown in Tables 1 to 3 were mixed and dissolved or dispersed using the stirrer in the compositions (parts by mass) shown in the respective tables to obtain photocuring materials shown in the tables.
- Synthesis Example 2 Synthesis of UP-2 In a reaction vessel equipped with a stirrer, 21.3 g (20.6 mmol) of modified polytetramethylene glycol having a number average molecular weight of 1034, 5.5 g (24.7 mmol) of isophorone diisocyanate and dibutyltin 0.05 g of dilaurate was charged, and the liquid temperature was raised from room temperature to 50 ° C. over 1 hour with stirring. Thereafter, a small amount was sampled and FT-IR was measured, and stirring was continued at 50 ° C. while confirming the absorption of isocyanate near 2300 cm ⁇ 1 .
- Synthesis Example 4 Synthesis of UP-4 A reaction vessel equipped with a stirrer was charged with 20 g (9 mmol) of terminal diol hydrogenated polybutadiene having a number average molecular weight of 2222, 4 g (18 mmol) of isophorone diisocyanate and 0.05 g of dibutyltin dilaurate and stirred. The liquid temperature was raised from room temperature to 50 ° C. over 1 hour. Thereafter, a small amount was sampled and FT-IR was measured, and stirring was continued at 50 ° C. while confirming the absorption of isocyanate near 2300 cm ⁇ 1 .
- Synthesis Example 5 Synthesis of UP-5 In place of 4 g of 3-aminopropyltriethoxysilane in Synthesis Example 4, 2 g (9.1 mmol) of 3-aminopropyltriethoxysilane and 1.17 g (9.00 mmol) of hydroxypropyl acrylate ) was added in the same manner as in Synthesis Example 4 to obtain a colorless transparent viscous liquid. This is designated as UP-5.
- UP-5 is a liquid polyurethane having a triethoxysilyl group introduced at one end and an acrylate group introduced at the other end.
- each of the compositions 1 shown in Tables 1 to 3 is placed in a hard fluororesin tube 2 having an inner diameter of 10 mm with the bottom surface closed with a fluororesin plug so that the liquid level is 50 mm.
- the upper 30 mm is shielded by the aluminum foil 3 while leaving the lower 20 mm.
- UV irradiation was performed for 2 seconds with a UV lamp 4 (100 mW / cm 2 manufactured by SEN Special Light Company).
- Comparative Examples 1 to 4 do not contain a chain transfer agent, it is shown that dark part curing does not proceed after 3 minutes after photocuring.
- Comparative Example 5 uses a commercially available moisture-curing silicone resin, and photocuring has not occurred, and it is shown that a sufficient cured portion cannot be seen when left for about 3 hours. This curing reaction can also be said to be a kind of anionic curing, but it is moisture curing depending only on the air, and in this case, it indicates that curing takes time.
- Comparative Examples 6 to 7 contained a chain transfer agent, and it was confirmed that curing of the dark part was proceeding by light irradiation.
- the chain curing agent does not contain an alkoxysilyl group capable of anion curing although it is radically curable. Therefore, the dark portion curing distance is the same as after 10 minutes even after being left for 3 hours, indicating that no post-curing has occurred.
- the dark part was cured after 10 minutes of light irradiation, and the curing distance was clearly increased after 3 hours. This indicates that anionic curing occurs as a post-curing reaction in addition to the conventional dark-curing that occurs in a chain.
- the curing of the dark part which could not be reached only by the chain photoradical reaction, is compensated by the subsequent anionic curing. This confirms that the photo-curing material of the present invention is capable of curing a portion where light is hard to reach by light irradiation.
- the dark portion curing is not performed by hydrolyzing the alkoxysilyl group and moisture curing, but in order to confirm that the hydroxy anion is involved in radical polymerization, evaluated.
- Table 4 shows examples and comparative examples with respect to dark part curing humidity dependency. The evaluation method is as follows.
- Examples 17 and 18 and Comparative Examples 8 to 10 were mixed with the composition (parts by mass) shown in Table 4 using a stirrer and dissolved or dispersed to obtain the photo-curing materials shown in Table 4.
- the photocuring material having the composition shown in Table 4 was placed in the apparatus shown in FIG. 1 and light shielding and ultraviolet irradiation were performed in the same manner. Two cured samples were prepared for each sample. One sample had a humidity of 23 ° C. and a humidity of 20%, and the other sample had a humidity of 23 ° C. and a humidity of 85%.
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Abstract
Description
光照射により硬化が可能な光硬化性液状組成物であって、
(メタ)アクリレートと連鎖移動剤を含有し、
前記連鎖移動剤が、ウレタン結合、尿素結合、又はイソシアネート基から選択される少なくとも1種を1個以上と、1個以上のアルコキシシリル基を含む化合物であることを要旨とするものである。
〔(メタ)アクリレート〕
・IBA:イソボルニルアクリレート
・DPGA:ジプロピレングリコールジアクリレート
・HPGA:ヘプタプロピレングリコールジアクリレート
〔連鎖移動剤〕
・UP-1(合成例1)
・UP-2(合成例2)
・UP-3(合成例3)
・UP-4(合成例4)
・UP-5(合成例5)
・UP-6(合成例6)
・UP-7(合成例7)
・UP-8(合成例8)
〔光(紫外線)重合開始剤〕
・HCHPK:1-ヒドロキシシクロヘキシルフェニルケトン
〔含金属化合物〕
・BPDZ:ビス(2,4-ペンタンジオナト)亜鉛(II)
〔シリコーン樹脂〕
・SE:市販湿気硬化樹脂SE-9186(東レダウコーニング社)
攪拌機を備えた反応容器に、数平均分子量が400のポリプロピレングリコール80g(200mmol)、ヘキサメチレンジイソシアネート40g(238mmol)とジブチルスズジラウレート0.05gを仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT-IRを測定して2300cm-1付近のイソシアネートの吸収を確認しながら、50℃にて攪拌を続けた。FT-IRの吸収面積から残留イソシアネート基の量がポリウレタンの末端のみになり、変化が無くなった時を反応終了とし、無色透明粘調性液体を得た。更に3-アミノプロピルトリエトキシシラン17.1g(77.2mmol)を仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT-IRを測定して2300cm-1付近のイソシアネートの吸収が消失した時を反応終了とし、無色透明粘調性液体を得た。これをUP-1とする。UP-1は両末端にトリエトキシシリル基が導入された液状ポリウレタンである。
攪拌機を備えた反応容器に、数平均分子量が1034の変性ポリテトラメチレングリコール21.3g(20.6mmol)、イソホロンジイソシアネート5.5g(24.7mmol)とジブチルスズジラウレート0.05gを仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT-IRを測定して2300cm-1付近のイソシアネートの吸収を確認しながら、50℃にて攪拌を続けた。FT-IRの吸収面積から残留イソシアネート基の量がポリウレタンの末端のみになり、変化が無くなった時を反応終了とし、無色透明粘調性液体を得た。更に3-アミノプロピルトリエトキシシラン1.84g(8.3mmol)を仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT-IRを測定して2300cm-1付近のイソシアネートの吸収が消失した時を反応終了とし、無色透明粘調性液体を得た。これをUP-2とする。UP-2は両末端にトリエトキシシリル基が導入された液状ポリウレタンである。
3-アミノプロピルトリエトキシシラン1.84gの代わりに、3-アミノプロピルトリエトキシシラン0.92g(4.15mmol)及びヒドロキシプロピルアクリレート0.54g(4.15mmol)を加えたこと以外は合成例2と同様に反応を行い無色透明粘調性液体を得た。これをUP-3とする。UP-3は一方の末端にトリエトキシシリル基が導入され、他方の末端にアクリレート基が導入された液状ポリウレタンである。
攪拌機を備えた反応容器に、数平均分子量が2222の末端ジオール水添ポリブタジエン20g(9mmol)、イソホロンジイソシアネート4g(18mmol)とジブチルスズジラウレート0.05gを仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT-IRを測定して2300cm-1付近のイソシアネートの吸収を確認しながら、50℃にて攪拌を続けた。FT-IRの吸収面積から残留イソシアネート基の量がポリウレタンの末端のみになり、変化が無くなった時を反応終了とし、無色透明粘調性液体を得た。更に3-アミノプロピルトリエトキシシラン4g(18.1mmol)を仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT-IRを測定して2300cm-1付近のイソシアネートの吸収が消失した時を反応終了とし、無色透明粘調性液体を得た。これをUP-4とする。UP-4は両末端にトリエトキシシリル基が導入された液状ポリウレタンである。
合成例4の3-アミノプロピルトリエトキシシラン4gの代わりに、3-アミノプロピルトリエトキシシラン2g(9.1mmol)及びヒドロキシプロピルアクリレート1.17g(9.00mmol)を加えたこと以外は、合成例4と同様に反応を行い無色透明粘調性液体を得た。これをUP-5とする。UP-5は一方の末端にトリエトキシシリル基が導入され他方の末端にアクリレート基が導入された液状ポリウレタンである。
合成例4の3-アミノプロピルトリエトキシシラン4gの代わりに、3-アミノプロピルトリメトキシシラン3.23g(18.0mmol)を加えたこと以外は、合成例4と同様に反応を行い無色透明粘調性液体を得た。これをUP-6とする。UP-6は両末端にトリメトキシシリル基が導入された液状ポリウレタンである。
合成例2の3-アミノプロピルトリエトキシシラン1.84gの代わりに、ヒドロキシプロピルアクリレート1.08g(8.3mmol)を加えたこと以外は、合成例2と同様に反応を行い無色透明粘調性液体を得た。これをUP-7とする。UP-7は両末端にアクリレート基が導入され、アルコキシシリル基を有していない液状ポリウレタンである。
合成例4の3-アミノプロピルトリエトキシシラン4gの代わりに、ヒドロキシプロピルアクリレート2.35g(18.1mmol)を加えたこと以外は合成例4と同様に反応を行い無色透明粘調性液体を得た。これをUP-8とする。UP-8は両末端にアクリレート基が導入され、アルコキシシリル基を有していない液状ポリウレタンである。
図1に示すように、表1~3に示す各組成物1それぞれを、底面をフッ素樹脂栓で塞いだ内径10mmの硬質フッ素樹脂チューブ2中に液面の高さが50mmになるように入れ、その下部20mmを残して上部30mmをアルミ箔3で遮光する。その側面からからUVランプ4(SEN特殊光源社製100mW/cm2)で2秒間紫外線照射を行った。その後、遮光下室温で10分間放置し、上部から1.5mm径のガラス棒を挿入し硬化部の確認を行うことによって、紫外線照射面と遮光面の境界Bから上部(非照射部)に進んだ硬化部の距離を計測した。尚硬化しているか否かについては指触による棒貫入可否にて判断した。その後、更に遮光下室温で3時間放置し、同様に硬化部の距離を計測した。この計測した値を硬化部距離(mm)として、表1~3に示し、硬化性の指標とした。すなわち硬化部距離が大きい程、暗部硬化性が高いことを示すものである。
比較例1~4は連鎖移動剤が含まれていないため、光硬化10分後、3時間後共に暗部硬化が進んでいないことを示している。比較例5は、市販の湿気硬化型シリコーン樹脂を用いており、光硬化は起きておらず、また3時間程度の放置では、十分な硬化箇所を見る事ができないことを示している。この硬化反応もアニオン硬化の一種と言えるが、空気中のみに依存して湿気硬化であり、その場合、硬化に時間を要することを示している。比較例6~7は連鎖移動剤が含まれ、光照射によって暗部硬化は進んでいる事が確認されたが、その連鎖硬化剤はラジカル硬化性ではあるもののアニオン硬化するアルコキシシリル基を含んでいないので、暗部硬化距離は3時間放置後も、10分後と同様で後硬化が起こっていないことを示している。これに対し、実施例1~16の本発明品では、光照射10分後は暗部硬化し、3時間後は更に硬化距離が明らかに大きくなっている。これは、従来の連鎖的に起こる暗部硬化に加え、アニオン硬化が後硬化反応として起きている事を示している。実施例では、連鎖的光ラジカル反応のみでは到達できなかった暗部の硬化が、その後のアニオン硬化で補われていることが示されている。これは、本発明の光硬化材料は、光照射によって、光がより届き難い箇所の硬化が可能になっている事を裏付けるものである。
本発明の光硬化材料における暗部硬化は、アルコキシシリル基が加水分解して湿気硬化するのではなく、ラジカル重合にヒドロキシアニオンが関与していることを確認するために、暗部硬化の湿度依存性を評価した。表4に暗部硬化湿度依存性に関し、実施例と比較例を示す。評価方法は下記の通りである。
表4に示すように比較例8の市販湿気硬化型シリコーン樹脂は、湿気硬化反応のみで硬化が進むため、湿度85%時の硬化距離が30mm以上と大きいが、湿度20%時の硬化距離が3.1mmと小さく、湿度が低いと硬化反応は遅かった。また比較例9、10は連鎖移動剤を含んでいるので、光硬化及び暗部硬化がある程度進行しているが、連鎖移動剤に湿気硬化性のアルコキシシリル基を含んでいないため、硬化反応は湿度に依存しないので湿度85%時でも硬化は進行していない。
Claims (4)
- 光照射により硬化が可能な光硬化性液状組成物であって、
(メタ)アクリレートと連鎖移動剤を含有し、
前記連鎖移動剤が、ウレタン結合、尿素結合、又はイソシアネート基から選択される少なくとも1種を1個以上と、1個以上のアルコキシシリル基を含む化合物であることを特徴とする光硬化材料。 - 更に含金属化合物を含むことを特徴とする請求項1記載の光硬化材料。
- 前記連鎖移動剤の含有量が、前記光硬化材料全体の10~90質量%の範囲内であることを特徴とする請求項1又は2記載の光硬化材料。
- 前記含金属化合物が、スズ、銅、亜鉛、コバルト、ニッケルのいずれかの金属化合物であることを特徴とする請求項2又は3記載の光硬化材料。
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- 2013-02-27 JP JP2013037321A patent/JP6061728B2/ja not_active Expired - Fee Related
- 2013-08-09 EP EP13876538.3A patent/EP2963061B1/en active Active
- 2013-08-09 US US14/767,703 patent/US9695270B2/en active Active
- 2013-08-09 KR KR1020157021531A patent/KR101688357B1/ko active IP Right Grant
- 2013-08-09 WO PCT/JP2013/071652 patent/WO2014132464A1/ja active Application Filing
- 2013-08-09 CN CN201380072832.8A patent/CN104995216B/zh not_active Expired - Fee Related
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WO2015151833A1 (ja) * | 2014-03-31 | 2015-10-08 | コニカミノルタ株式会社 | 光硬化性組成物、及びそれを含有する光硬化性インクジェットインク、光硬化性組成物を用いた記録方法、並びに光硬化性インクジェットインクを用いた記録方法 |
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WO2015174371A1 (ja) * | 2014-05-13 | 2015-11-19 | 積水化学工業株式会社 | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 |
JP5844504B1 (ja) * | 2014-05-13 | 2016-01-20 | 積水化学工業株式会社 | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 |
Also Published As
Publication number | Publication date |
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US20160002388A1 (en) | 2016-01-07 |
KR20150104627A (ko) | 2015-09-15 |
JP6061728B2 (ja) | 2017-01-18 |
CN104995216A (zh) | 2015-10-21 |
JP2014162892A (ja) | 2014-09-08 |
EP2963061B1 (en) | 2020-04-01 |
CN104995216B (zh) | 2016-12-07 |
US9695270B2 (en) | 2017-07-04 |
EP2963061A4 (en) | 2016-07-27 |
EP2963061A1 (en) | 2016-01-06 |
KR101688357B1 (ko) | 2016-12-20 |
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