CN117480194A - Photo-moisture curable resin composition, adhesive for electronic component, cured body, and electronic component - Google Patents
Photo-moisture curable resin composition, adhesive for electronic component, cured body, and electronic component Download PDFInfo
- Publication number
- CN117480194A CN117480194A CN202280040313.2A CN202280040313A CN117480194A CN 117480194 A CN117480194 A CN 117480194A CN 202280040313 A CN202280040313 A CN 202280040313A CN 117480194 A CN117480194 A CN 117480194A
- Authority
- CN
- China
- Prior art keywords
- moisture
- curable resin
- photo
- meth
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 154
- 239000000853 adhesive Substances 0.000 title claims description 47
- 230000001070 adhesive effect Effects 0.000 title claims description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 214
- 239000011347 resin Substances 0.000 claims abstract description 77
- 229920005989 resin Polymers 0.000 claims abstract description 77
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000003999 initiator Substances 0.000 claims abstract description 22
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 85
- 239000000758 substrate Substances 0.000 claims description 25
- 239000011521 glass Substances 0.000 claims description 19
- 229910052782 aluminium Inorganic materials 0.000 claims description 17
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 17
- 239000000945 filler Substances 0.000 claims description 16
- -1 nitrogen-containing compound Chemical class 0.000 description 173
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 155
- 150000003254 radicals Chemical class 0.000 description 69
- 229920005862 polyol Polymers 0.000 description 53
- 239000005056 polyisocyanate Substances 0.000 description 47
- 229920001228 polyisocyanate Polymers 0.000 description 47
- 239000004417 polycarbonate Substances 0.000 description 35
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 34
- 150000003077 polyols Chemical class 0.000 description 32
- 239000002994 raw material Substances 0.000 description 31
- 229920000515 polycarbonate Polymers 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
- 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 26
- 239000012948 isocyanate Substances 0.000 description 25
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- 239000004721 Polyphenylene oxide Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- 238000013008 moisture curing Methods 0.000 description 21
- 229920000570 polyether Polymers 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 17
- 150000002513 isocyanates Chemical class 0.000 description 17
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000004970 Chain extender Substances 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 150000002009 diols Chemical class 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 238000000016 photochemical curing Methods 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 11
- 150000001252 acrylic acid derivatives Chemical group 0.000 description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 229930195734 saturated hydrocarbon Natural products 0.000 description 10
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 9
- 239000003086 colorant Substances 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 229920005906 polyester polyol Polymers 0.000 description 9
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 230000002194 synthesizing effect Effects 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 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
- 239000003054 catalyst Substances 0.000 description 5
- 229920000620 organic polymer Polymers 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920006389 polyphenyl polymer Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- 229940035437 1,3-propanediol Drugs 0.000 description 3
- 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 3
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 3
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-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
- 239000000654 additive Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 3
- 235000019437 butane-1,3-diol Nutrition 0.000 description 3
- 150000004292 cyclic ethers Chemical group 0.000 description 3
- 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 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-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
- 239000007788 liquid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 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 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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 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
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 2
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 2
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004839 3-methylpentylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])C([H])([H])[*:1])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 101100001347 Mus musculus Akt1s1 gene Proteins 0.000 description 2
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical compound [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 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 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- 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 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- WWVBRUMYFUDEJQ-UHFFFAOYSA-N 1-ethoxyethane-1,2-diol Chemical compound CCOC(O)CO WWVBRUMYFUDEJQ-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
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-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
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-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
- VJZBTBIZXCDAMV-UHFFFAOYSA-N 2-(1,3-dioxo-5,6,7,7a-tetrahydro-4h-isoindol-3a-yl)ethyl prop-2-enoate Chemical compound C1CCCC2C(=O)NC(=O)C21CCOC(=O)C=C VJZBTBIZXCDAMV-UHFFFAOYSA-N 0.000 description 1
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-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
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical group CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-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
- 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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- FIMAGFSGWNAHTD-UHFFFAOYSA-N 3,5,8-trimethyl-1,4-diazabicyclo[2.2.2]octane Chemical group C1C(C)N2C(C)CN1CC2C FIMAGFSGWNAHTD-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- UVRCNEIYXSRHNT-UHFFFAOYSA-N 3-ethylpent-2-enamide Chemical compound CCC(CC)=CC(N)=O UVRCNEIYXSRHNT-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- PENRYFPQHOTBJV-UHFFFAOYSA-N 4-(3-morpholin-4-ylpropyl)morpholine Chemical compound C1COCCN1CCCN1CCOCC1 PENRYFPQHOTBJV-UHFFFAOYSA-N 0.000 description 1
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical group CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- UVNYQSUCIGWUHW-UHFFFAOYSA-N N=C=O.CCCC Chemical compound N=C=O.CCCC UVNYQSUCIGWUHW-UHFFFAOYSA-N 0.000 description 1
- QMOWYWSHERGNQQ-UHFFFAOYSA-N N=C=O.CCCCCCCCCC Chemical compound N=C=O.CCCCCCCCCC QMOWYWSHERGNQQ-UHFFFAOYSA-N 0.000 description 1
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- XBXFGOSIPGWNLZ-UHFFFAOYSA-N O=C1C=C(CC(C)(C)C1)C.N=C=O Chemical compound O=C1C=C(CC(C)(C)C1)C.N=C=O XBXFGOSIPGWNLZ-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- LAGWVZPUXSKERV-UHFFFAOYSA-N cyclohexane;isocyanic acid Chemical compound N=C=O.C1CCCCC1 LAGWVZPUXSKERV-UHFFFAOYSA-N 0.000 description 1
- KMFRQYRLHPRIOX-UHFFFAOYSA-N cyclopentane;isocyanic acid Chemical compound N=C=O.C1CCCC1 KMFRQYRLHPRIOX-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 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 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- BQBKYSPXQYHTIP-UHFFFAOYSA-N ethyl n-butylcarbamate Chemical compound CCCCNC(=O)OCC BQBKYSPXQYHTIP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KPYCPQVKYYJPIY-UHFFFAOYSA-N hexane;isocyanic acid Chemical compound N=C=O.CCCCCC KPYCPQVKYYJPIY-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- QYRRPQSBTOLXQR-UHFFFAOYSA-N methoxy-[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(O[SiH2]OC)(C)C QYRRPQSBTOLXQR-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- ZZHGIUCYKGFIPV-UHFFFAOYSA-M n-butylcarbamate Chemical compound CCCCNC([O-])=O ZZHGIUCYKGFIPV-UHFFFAOYSA-M 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000006884 silylation reaction Methods 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
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 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
- 230000009974 thixotropic effect Effects 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- 238000002834 transmittance Methods 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical group C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
- C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09J201/025—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The photo-moisture-curable resin composition comprises a radical-polymerizable compound (A), a moisture-curable resin (B), a photopolymerization initiator (C), and a compound (D) having 3 or more isocyanate groups in the molecule.
Description
Technical Field
The invention relates to a photo-moisture curable resin composition, an adhesive for electronic components, a cured body, and an electronic component.
Background
In recent years, high integration and miniaturization have been demanded for electronic components such as semiconductor chips, and for example, a plurality of thin semiconductor chips may be bonded to each other via an adhesive layer to form a semiconductor chip laminate. In addition, in modern times in which mobile devices having various display elements are used, an operation of narrowing the frame of an image display portion (hereinafter, also referred to as "narrow frame design") is performed as a method of downsizing the display elements. In these applications, with miniaturization and narrowing of the frame, it has been attempted to use a photo moisture curable adhesive instead of a double sided tape.
As a photo moisture curable adhesive, for example, patent document 1 discloses a photo moisture curable resin composition containing a radical polymerizable compound, a moisture curable urethane resin, a photo radical polymerization initiator, and a moisture removing agent. Here, the moisture removing agent is blended to improve storage stability and the like, and a compound having at least 1 group selected from an isocyanate group, an isothiocyanate group, and a carbodiimide group is exemplified.
Prior art literature
Patent literature
Patent document 1: international publication No. 2015/111567
Disclosure of Invention
Problems to be solved by the invention
The photo-moisture curable adhesive is generally cured by light to be in a B-stage state, the adherends are bonded to each other by the photo-moisture curable adhesive in the B-stage state, and then the adherends are generally bonded to each other by moisture curing.
In addition, depending on the use environment, the photo-moisture curable adhesive is sometimes required to maintain high adhesion (final heat-resistant adhesion) even in a high-temperature environment after the main adhesion. For example, when the adhesive is used for electronic parts, the adhesive may be heated to a high temperature by heat generated from the electronic parts, and thus the final heat-resistant adhesive may be required to be high.
However, the photo-moisture curable adhesive may not have sufficient final heat-resistant adhesive strength after the main adhesion depending on the blending thereof. For example, since the photo moisture curable adhesive is often insufficient in adhesive force (initial adhesive force) in a B-stage state immediately after photo curing, it is considered to increase the initial adhesive force by performing an operation such as increasing the molecular weight of the prepolymer contained therein. However, if the molecular weight of the prepolymer is increased, the bulk strength (bulk strength) of the cured product tends to be low, and the heat-resistant adhesive strength tends to be low in the end.
Accordingly, an object of the present invention is to provide a photo-moisture curable resin composition having excellent heat-resistant adhesion after moisture curing.
Means for solving the problems
The present inventors have conducted intensive studies and as a result, have found that the above problems can be solved by including a compound (D) having 3 or more isocyanate groups in the molecule in addition to the radical polymerizable compound (a), the moisture curable resin (B) and the photopolymerization initiator (C) in the photo moisture curable resin composition, and have completed the present invention. That is, the present invention provides the following [1] to [29].
[1] A photo-moisture-curable resin composition comprising a radical-polymerizable compound (A), a moisture-curable resin (B), a photopolymerization initiator (C), and a compound (D) having 3 or more isocyanate groups in the molecule.
[2] The photo-moisture-curable resin composition according to the above [1], wherein the compound (D) contains a compound having 5 or more isocyanate groups in the molecule.
[3]According to [1] above]Or [2]]The photo-moisture curable resin composition was applied to an aluminum substrate with a line width of 1.0mm, and irradiated with 1000mJ/cm 2 When the glass plate is pressed for 120 seconds at 0.08MPa in a state where the ultraviolet light is cured, a/b is 0.5 to 0.99 inclusive, if a is the average width of the bonding portion on the glass plate side and b is the average width of the bonding portion on the aluminum substrate side.
[4] The photo-moisture curable resin composition according to any one of the above [1] to [3], wherein the viscosity is 40 Pa.s or more and 600 Pa.s or less as measured using a cone-plate viscometer under conditions of 25℃and 5.0 rpm.
[5] The photo-moisture-curable resin composition according to any one of [1] to [4], wherein the moisture-curable resin (B) comprises a moisture-curable urethane resin.
[6] The photo-moisture curable resin composition according to any one of [1] to [5], wherein the moisture curable urethane resin is a moisture curable urethane resin having at least any one of a polycarbonate skeleton, a polyether skeleton, and a polyester skeleton.
[7] The photo-moisture-curable resin composition according to any one of [1] to [7], wherein the moisture-curable urethane resin is a moisture-curable urethane resin having a polycarbonate skeleton.
[8] The photo-moisture curable resin composition according to any one of [1] to [7], wherein the weight average molecular weight of the moisture curable resin (B) is 7500 to 24000.
[9] The photo-moisture curable resin composition according to any one of the above [1] to [8], wherein the radical polymerizable compound (A) comprises a monofunctional radical polymerizable compound.
[10] The photo-moisture curable resin composition according to the above [9], which contains 90 parts by mass or more of a monofunctional radical polymerizable compound per 100 parts by mass of the radical polymerizable compound (A).
[11] The photo-moisture curable resin composition according to the above [9] or [10], wherein the monofunctional radical polymerizable compound contains a nitrogen-containing compound.
[12] The photo-moisture curable resin composition according to the above [11], wherein the monofunctional radical polymerizable compound contains a chain-like nitrogen-containing compound.
[13] The photo-moisture curable resin composition according to the above [11] or [12], wherein the monofunctional radical polymerizable compound contains a cyclic nitrogen-containing compound.
[14] The photo-moisture-curable resin composition according to the above [13], wherein a mass ratio (cyclic/chain) of the nitrogen-containing compound having a cyclic structure to the chain-like nitrogen-containing compound is 0.1 to 2.0.
[15] The photo moisture curable resin composition according to any one of [11] to [14], wherein the content of the nitrogen-containing compound as the monofunctional radical polymerizable compound is 10 parts by mass or more and 95 parts by mass or less relative to 100 parts by mass of the radical polymerizable compound (A).
[16] The photo-moisture curable resin composition according to any one of [11] to [15], wherein the monofunctional radical polymerizable compound contains a monofunctional (meth) acrylate compound in addition to the nitrogen-containing compound.
[17] The photo-moisture-curable resin composition according to the above [16], wherein the monofunctional (meth) acrylate compound is at least 1 selected from the group consisting of alkyl (meth) acrylates, alicyclic structure-containing (meth) acrylates, and aromatic ring-containing (meth) acrylates.
[18] The photo moisture curable resin composition according to the above [17], wherein the total content of the alkyl (meth) acrylate, the alicyclic structure-containing (meth) acrylate, and the aromatic ring-containing (meth) acrylate is 5 parts by mass or more and 90 parts by mass or less relative to 100 parts by mass of the radical polymerizable compound (A).
[19] The photo-moisture-curable resin composition according to any one of [1] to [18], wherein a mass ratio (B/A) of the moisture-curable resin (B) to the radical-polymerizable compound (A) is 30/70 or more and 90/10 or less.
[20] The photo-moisture curable resin composition according to any one of the above [1] to [19], further comprising a filler (E).
[21] The photo-moisture curable resin composition according to any one of [1] to [20], wherein the photopolymerization initiator (C) is at least 1 selected from the group consisting of benzophenone-based compounds, acetophenone-based compounds, alkylbenzene-based photopolymerization initiators, acylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin ether-based compounds, and thioxanthones.
[22] The photo moisture curable resin composition according to any one of the above [1] to [21], wherein the compound (D) is at least 1 selected from the group consisting of a biuret modified form of a polyisocyanate, an isocyanurate modified form of a polyisocyanate, a polyol modified form of a polyisocyanate, and a polymeric MDI.
[23] The photo moisture curable resin composition according to any one of the above [1] to [22], wherein the compound (D) is at least 1 selected from the group consisting of isocyanurate modified polyisocyanates and polymeric MDI.
[24] The photo-moisture curable resin composition according to any one of the above [1] to [23], wherein the initial adhesion is 0.1MPa or more.
[25] The photo-moisture curable resin composition according to any one of the above [1] to [24], which has a final heat-resistant adhesion of 1.0MPa or more.
[26] The photo-moisture curable resin composition according to any one of [1] to [25], wherein the content of the compound (D) is 0.1 parts by mass or more and 10 parts by mass or less relative to 100 parts by mass of the total of the radical polymerizable compound (A) and the moisture curable resin (B).
[27] An adhesive for electronic parts, which is composed of the photo-moisture curable resin composition of any one of the above [1] to [26 ].
[28] A cured product of the photo-moisture curable resin composition according to any one of the above [1] to [26 ].
[29] An electronic component comprising the cured product of [28 ].
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, an photo moisture curable resin composition having excellent heat resistance adhesion after moisture curing can be provided.
Drawings
FIG. 1 is a conceptual diagram showing a method of measuring the internal/external ratio a/b.
Fig. 2 is a schematic view showing an adhesion test method, fig. 2 (a) is a plan view, and fig. 2 (b) is a side view.
Detailed Description
The present invention will be described in detail with reference to embodiments.
< photo moisture curable resin composition >
The photo-moisture-curable resin composition of the present invention comprises a radical-polymerizable compound (A), a moisture-curable resin (B), a photopolymerization initiator (C), and a compound (D) having 3 or more isocyanate groups in the molecule.
The components contained in the photo moisture curable resin composition will be described in more detail below.
[ radically polymerizable Compound (A) ]
The photo moisture curable resin composition of the present invention contains a radical polymerizable compound (a). The photo-moisture curable resin composition is provided with photo-curability by containing the radical polymerizable compound (a). The photo-moisture curable resin composition has photo-curability, and thus can impart a predetermined adhesive force only by irradiation with light, and thus can ensure a predetermined initial adhesive force.
The radical polymerizable compound (a) may have a radical polymerizable functional group in the molecule. The radical polymerizable functional group is preferably a compound having an unsaturated double bond, and examples thereof include a (meth) acryloyl group, a vinyl group, a styryl group, and an allyl group.
Among the above, (meth) acryl is preferable from the viewpoint of adhesion, that is, the radical polymerizable compound (a) preferably contains a compound having a (meth) acryl. The compound having a (meth) acryloyl group is hereinafter also referred to as a "(meth) acrylic compound". In the present specification, "(meth) acryl" means acryl or (meth) acryl, and "(meth) acrylic" means acrylic or methacrylic, and other similar terms are also used.
The radical polymerizable compound (a) may contain one or both of a monofunctional radical polymerizable compound having 1 radical polymerizable functional group in 1 molecule and a polyfunctional radical polymerizable compound having 2 or more radical polymerizable functional groups in 1 molecule, but from the viewpoint of improving the initial adhesion of the photo moisture curable resin composition, it is preferable to contain a monofunctional radical polymerizable compound. Further, the radical polymerizable compound (a) more preferably contains at least a monofunctional (meth) acrylic compound as a monofunctional radical polymerizable compound. The monofunctional radical polymerizable compound may be a prepolymer having a repeating unit which is polymerized, but a monofunctional monomer having no repeating unit is usually preferably used.
In the photo moisture curable resin composition, the monofunctional radical polymerizable compound may be, for example, 50 parts by mass or more and 100 parts by mass or less with respect to 100 parts by mass of the radical polymerizable compound (a).
In addition, in order to improve the initial adhesion of the photo moisture curable resin composition, the photo moisture curable resin composition preferably contains a monofunctional radical polymerizable compound in a large amount. Specifically, the photo moisture curable resin composition preferably contains 90 parts by mass or more, preferably 95 parts by mass or more, and more preferably 100 parts by mass of the monofunctional radical polymerizable compound (a) per 100 parts by mass of the radical polymerizable compound (a).
[ monofunctional radically polymerizable Compound ]
(Nitrogen-containing Compound)
The radical polymerizable compound (a) preferably contains a nitrogen-containing compound as a monofunctional radical polymerizable compound. By using the nitrogen-containing compound, the initial adhesion of the photo moisture curable resin composition becomes good. The photo-moisture curable resin composition is applied to an adherend and then cured by irradiation with active energy rays such as ultraviolet rays, but in this case, it is generally cured by light in the presence of oxygen as will be described later. If the radical polymerizable compound (a) contains a nitrogen-containing compound, the radical polymerizable compound (a) is suitably photo-cured in the presence of oxygen, and thus, it is presumed that the initial adhesion is good.
The nitrogen-containing compound may contain one or both of a chain-like nitrogen-containing compound and a nitrogen-containing compound having a cyclic structure, but from the viewpoint of improving the initial adhesion of the photo moisture-curable resin composition, it is preferable to contain a nitrogen-containing compound having a cyclic structure, and it is more preferable to use a chain-like nitrogen-containing compound in combination with a nitrogen-containing compound having a cyclic structure.
Examples of the nitrogen-containing compound having a cyclic structure include nitrogen-containing compounds having a lactam structure such as N-vinylpyrrolidone and N-vinyl-. Epsilon. -caprolactam, compounds having a morpholine skeleton such as N-acryloylmorpholine, and cyclic imide compounds such as N- (meth) acryloyloxyethyl hexahydrophthalimide. Among them, an amide group-containing compound such as N-vinylcaprolactam is more preferable. In the present specification, a nitrogen-containing compound having a cyclic structure is also referred to as a cyclic nitrogen-containing compound, a radical polymerizable compound having a nitrogen atom included in an atom constituting the ring itself is referred to as a cyclic nitrogen-containing compound, and other nitrogen-containing compounds are referred to as chain-like nitrogen-containing compounds.
Examples of the chain nitrogen-containing compound include chain (meth) acrylic acid esters such as dimethylamino (meth) acrylic acid esters, diethylamino (meth) acrylic acid esters, aminomethyl (meth) acrylic acid esters, aminoethyl (meth) acrylic acid esters, dimethylaminoethyl (meth) acrylic acid esters, and the like, chain (meth) acrylamide compounds such as diacetone acrylamide, N-dimethylacrylamide, N-diethylacrylamide, N-isopropylacrylamide, N-hydroxyethyl acrylamide, and methacrylamide, and N-vinylacetamide.
The nitrogen-containing compound in the form of a chain may be a monofunctional urethane (meth) acrylate. By using a monofunctional urethane (meth) acrylate, when a urethane resin, particularly a urethane resin having a polycarbonate skeleton, is used as the moisture-curable resin (B), compatibility with the moisture-curable resin (B) is improved, and initial adhesion is easily improved. In addition, since urethane (meth) acrylate has a high polarity, it is easy to increase the adhesion to glass.
As the monofunctional urethane (meth) acrylate, for example, a (meth) acrylic acid derivative having a hydroxyl group is reacted with an isocyanate compound.
Examples of the (meth) acrylic acid derivative having a hydroxyl group include mono (meth) acrylic acid esters of dihydric alcohols such as ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 3-butanediol, 1, 4-butanediol, and polyethylene glycol, and mono (meth) acrylic acid esters of trihydric alcohols such as trimethylolethane, trimethylolpropane, and glycerin.
Examples of the isocyanate compound used for obtaining the urethane (meth) acrylate include an alkane monoisocyanate such as butane isocyanate, hexane isocyanate and decane isocyanate, an aliphatic monoisocyanate such as a cyclic aliphatic monoisocyanate such as cyclopentane isocyanate, cyclohexane isocyanate and isophorone monoisocyanate.
More specifically, the monofunctional urethane (meth) acrylate is preferably a urethane (meth) acrylate obtained by reacting the above-mentioned monoisocyanate compound with a mono (meth) acrylate of a diol, and specific examples thereof include 1, 2-ethylene glycol 1-acrylate 2- (N-butylurethane).
Among the above, the chain-like nitrogen-containing compound preferably contains a monofunctional urethane (meth) acrylate, and it is also preferable to use a monofunctional urethane (meth) acrylate in combination with a compound other than the monofunctional urethane (meth) acrylate, such as a (meth) acrylamide compound.
The content of the nitrogen-containing compound as the monofunctional radical polymerizable compound in the photo moisture curable resin composition is preferably 10 parts by mass or more, more preferably 30 parts by mass or more, still more preferably 50 parts by mass or more, still more preferably 60 parts by mass or more, and most preferably 75 parts by mass or more, based on 100 parts by mass of the radical polymerizable compound (a), from the viewpoint of improving the initial adhesion of the photo moisture curable resin composition. The content of the nitrogen-containing compound as the monofunctional radically polymerizable compound is preferably 95 parts by mass or less, more preferably 90 parts by mass or less, and further preferably 85 parts by mass or less, in order to properly contain the radically polymerizable compound (a) other than the nitrogen-containing compound.
In the case where the monofunctional radically polymerizable compound has a chain-shaped nitrogen-containing compound and a nitrogen-containing compound having a cyclic structure, the mass ratio (cyclic/chain-shaped) of the nitrogen-containing compound having a cyclic structure to the chain-shaped nitrogen-containing compound in the monofunctional radically polymerizable compound is preferably 0.1 or more and 2.0 or less, more preferably 0.2 or more and 1.5 or less, and still more preferably 0.4 or more and 1.2 or less. When the mass ratio of the ring-shaped form to the chain form is in the above range, the initial adhesion of the photo moisture curable resin composition can be improved.
(monofunctional radical polymerizable Compound other than Nitrogen-containing Compound)
The monofunctional radical polymerizable compound contained in the radical polymerizable compound (a) preferably contains a compound other than the above-described nitrogen-containing compound (hereinafter, also referred to as a non-nitrogen-containing compound). The radically polymerizable compound (a) contains a non-nitrogen-containing compound as a monofunctional radically polymerizable compound, and thus, the adhesion and the like can be easily improved.
The non-nitrogen-containing compound is not particularly limited as long as it has a radical polymerizable functional group, but is preferably a monofunctional (meth) acrylic compound, and among these, a (meth) acrylate compound is more preferably exemplified.
Examples of the monofunctional (meth) acrylate compound include alkyl (meth) acrylate, alicyclic structure-containing (meth) acrylate, aromatic ring-containing (meth) acrylate, and the like. These may be used alone or in combination of 1 or 2 or more, but one or both of alkyl (meth) acrylate and aromatic ring-containing (meth) acrylate are preferably used.
The total content of the alkyl (meth) acrylate, the alicyclic structure-containing (meth) acrylate, and the aromatic ring-containing (meth) acrylate in the radical polymerizable compound (a) is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and still more preferably 15 parts by mass or more, based on 100 parts by mass of the radical polymerizable compound (a). The content is preferably 90 parts by mass or less, more preferably 70 parts by mass or less, still more preferably 60 parts by mass or less, still more preferably 40 parts by mass or less, and most preferably 25 parts by mass or less.
Examples of the alkyl (meth) acrylate include alkyl (meth) acrylates having 1 to 18 carbon atoms in the alkyl group such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, and the like.
Examples of the alicyclic structure-containing (meth) acrylate include alicyclic structure-containing (meth) acrylates such as cyclohexyl (meth) acrylate, 4-t-butylcyclohexyl (meth) acrylate, 3, 5-trimethylcyclohexyl (meth) acrylate, isobornyl (meth) acrylate, and dicyclopentenyl (meth) acrylate. The alicyclic structure is a ring structure in which a ring constituent element is composed of carbon atoms.
Examples of the aromatic ring-containing (meth) acrylate include phenyl alkyl (meth) acrylate such as benzyl (meth) acrylate and 2-phenyl ethyl (meth) acrylate, and phenoxyalkyl (meth) acrylate such as phenoxyethyl (meth) acrylate.
As the monofunctional (meth) acrylate compound, in addition to the alkyl (meth) acrylate, the alicyclic structure-containing (meth) acrylate, and the aromatic ring-containing (meth) acrylate, for example, a cyclic ether group-containing (meth) acrylate may be used.
Examples of the cyclic ether group-containing (meth) acrylate include epoxy, oxetane, tetrahydrofuran, dioxolane, and dioxane(meth) acrylic esters of an alkane ring and the like.
Examples of the epoxy ring-containing (meth) acrylate include glycidyl (meth) acrylate. Examples of the oxetan ring-containing (meth) acrylate include (3-ethyloxetan-3-yl) methyl (meth) acrylate. As the tetrahydrofuran ring-containing (meth) acrylic acid ester, there may be mentioned tetrahydrofuran (meth) acrylateEsters of alkyl (meth) acrylic acid polymers of tetrahydrofurfuryl alcohol, and the like. Examples of the dioxolane-containing (meth) acrylate include (2-methyl-2-ethyl-1, 3-dioxolan-4-yl) methyl (meth) acrylate and (2, 2-cyclohexyl-1, 3-dioxolan-4-yl) methyl (meth) acrylate. As a double-sided tapeExamples of the (meth) acrylate of the alkyl ring include cyclic trimethylolpropane formal (meth) acrylate and the like.
As the (meth) acrylate containing a cyclic ether group, either one of a (meth) acrylate containing an oxetane ring and a (meth) acrylate containing a tetrahydrofuran ring is preferably used, but a combination of these is also preferable.
Further, as the monofunctional (meth) acrylate compound, polyoxyethylene (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate and the like, hydroxyalkyl (meth) acrylate such as 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate and the like, alkoxyethylene glycol (meth) acrylates such as methoxyethylene glycol (meth) acrylate, ethoxyethylene glycol (meth) acrylate and the like, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, ethylcarbitol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, ethoxytriethylene glycol (meth) acrylate, ethoxypolyethylene glycol (meth) acrylate and the like can be used.
Further, as the monofunctional (meth) acrylic compound, a (meth) acrylic compound containing a carboxyl group such as acrylic acid or methacrylic acid, or the like can be used.
[ Compounds other than monofunctional radically polymerizable Compounds ]
The radical polymerizable compound (a) may contain a polyfunctional radical polymerizable compound as long as the effect of the present invention is exhibited. Examples of the polyfunctional radically polymerizable compound include 2-functional (meth) acrylate compounds, 3-functional or more (meth) acrylate compounds, and 2-functional or more urethane (meth) acrylates.
Examples of the 2-functional (meth) acrylate compound include, 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 10-decanediol di (meth) acrylate, 2-n-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, ethylene oxide addition bisphenol A di (meth) acrylate, propylene oxide addition bisphenol A di (meth) acrylate, ethylene oxide addition bisphenol F di (meth) acrylate, dimethylol dicyclopentadiene di (meth) acrylate, neopentyl glycol di (meth) acrylate, 2-hydroxy-3- (meth) acryloxypropyl (meth) acrylate, carbonate diol di (meth) acrylate, polyether diol di (meth) acrylate, polyester diol di (meth) acrylate, caprolactone di (meth) acrylate, polybutadiene diol di (meth) acrylate, and the like.
Examples of the 3-functional or higher (meth) acrylate compound include trimethylolpropane tri (meth) acrylate, ethylene oxide addition trimethylolpropane tri (meth) acrylate, propylene oxide addition trimethylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide addition glycerol tri (meth) acrylate, tri (meth) acryloyloxyethyl phosphate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.
As the urethane (meth) acrylate having a function of 2 or more, for example, a (meth) acrylic acid derivative having a hydroxyl group and an isocyanate compound are reacted.
Examples of the (meth) acrylic acid derivative having a hydroxyl group include mono (meth) acrylic acid esters of dihydric alcohols such as ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 3-butanediol, 1, 4-butanediol, and polyethylene glycol, mono (meth) acrylic acid esters or di (meth) acrylic acid esters of trihydric alcohols such as trimethylolethane, trimethylolpropane, and glycerin, and epoxy (meth) acrylic acid esters such as bisphenol a type epoxy (meth) acrylic acid esters.
Examples of the isocyanate compound used for obtaining the urethane (meth) acrylate include polyisocyanate compounds such as isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, 1, 6-hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethylxylylene diisocyanate, and 1,6, 11-undecane triisocyanate.
Further, as the isocyanate compound, a chain-extended polyisocyanate compound (polyol modified body) obtained by reacting a polyol with an excessive isocyanate compound may also be used. Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol.
By using these polyisocyanate compounds, a multifunctional urethane (meth) acrylate can be obtained.
[ moisture-curable resin (B) ]
The moisture-curable resin (B) used in the present invention includes, for example, a moisture-curable urethane resin, a resin containing a hydrolyzable silyl group, a moisture-curable cyanoacrylate resin, and the like, and is preferably any one of the moisture-curable urethane resin and the resin containing a hydrolyzable silyl group, and more preferably the moisture-curable urethane resin. The number of these may be 1 alone or 2 or more.
(moisture-curable urethane resin)
The moisture-curable urethane resin can be obtained by reacting a polyol compound having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule. The moisture-curable urethane resin preferably has an isocyanate group in a molecule, and the isocyanate group in the molecule is cured by reacting with moisture in the air or in an adherend. The moisture-curable urethane resin may have only 1 isocyanate group or 2 or more isocyanate groups in 1 molecule, but the moisture-curable urethane resin preferably has 1 or 2 isocyanate groups in 1 molecule, more preferably has 2 isocyanate groups. The isocyanate groups are not particularly limited, but are preferably provided at the ends of the moisture-curable urethane resin, for example, at both ends.
The reaction of the polyol compound and the polyisocyanate compound is usually carried out in a molar ratio of hydroxyl groups (OH) in the polyol compound to isocyanate groups (NCO) in the polyisocyanate compound in the range of [ NCO ]/[ OH ] =2.0 to 2.5.
As the polyol compound serving as a raw material of the moisture-curable urethane resin, a known polyol compound generally used in the production of polyurethane can be used, and examples thereof include polyester polyol, polyether polyol, polyalkylene polyol, polycarbonate polyol, and the like. These polyol compounds may be used alone or in combination of 1 or more than 2.
The moisture-curable urethane resin is preferably at least one of a moisture-curable urethane resin having a polycarbonate skeleton, a polyether skeleton, or a polyester skeleton, more preferably at least one of a moisture-curable urethane resin having a polycarbonate skeleton or a polyether skeleton, and still more preferably a moisture-curable urethane resin having a polycarbonate skeleton. The moisture-curable urethane resin has a polycarbonate skeleton, so that heat resistance, mechanical strength, and the like are increased, and both initial adhesion and final heat-resistant adhesion are easily excellent. Further, a photo moisture curable resin composition excellent in weather resistance, moisture resistance and the like of a cured product can be provided.
(moisture-curable urethane resin having a polycarbonate skeleton)
The moisture-curable urethane resin having a polycarbonate skeleton is obtained by introducing a polycarbonate skeleton into a urethane resin by using a polycarbonate polyol as the polyol compound. The moisture-curable urethane resin having a polycarbonate skeleton can be obtained, for example, by reacting a polycarbonate polyol having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
The polycarbonate polyol is preferably a polycarbonate diol, and specific preferable examples of the polycarbonate diol include compounds represented by the following formula (1).
In the formula (1), R is a divalent hydrocarbon group having 4 to 16 carbon atoms, and n is an integer of 2 to 500.
In formula (1), R is preferably an aliphatic saturated hydrocarbon group. R is an aliphatic saturated hydrocarbon group, and thus heat resistance tends to be excellent. Further, yellowing and the like are less likely to occur due to thermal degradation and the like, and weather resistance is also good. R composed of an aliphatic saturated hydrocarbon group may have a chain structure or a cyclic structure, but is preferably a chain structure in view of easy stress relaxation and good flexibility. The R of the chain structure may be either a straight chain or a branched chain.
n is preferably 5 to 200, more preferably 10 to 150, and even more preferably 20 to 50.R is preferably 5 to 12.
The R contained in the polycarbonate polyol constituting the moisture-curable urethane resin may be used alone or in combination of 1 or more than 2. When 2 or more kinds of aliphatic saturated hydrocarbon groups are used in combination, at least a part of the aliphatic saturated hydrocarbon groups preferably have a carbon number of 6 or more.
The chain aliphatic saturated hydrocarbon group having 6 or more carbon atoms is preferably 6 to 12 carbon atoms, more preferably 6 to 10 carbon atoms, still more preferably 6 to 8 carbon atoms.
Specific examples of R include straight-chain ones such as 1, 4-butylene, pentylene, 1, 6-hexylene, 1, 7-heptylene, 1, 8-octylene, 1, 9-nonylene and 1, 10-decylene, and branched ones such as methylpentylene such as 3-methylpentylene and methyl 1, 8-octylene. 1 may be the same or different from each other. Thus, 2 or more kinds of R may be contained in one molecule, in which case 2 or 3 kinds of R are preferably contained in one molecule. For example, the polycarbonate polyol may be a copolymer containing 1 molecule of R having 6 or less carbon atoms and R having 7 or more carbon atoms, and in this case, it is preferable that each R is a chain aliphatic saturated hydrocarbon group.
R may include a linear aliphatic saturated hydrocarbon group or a branched aliphatic saturated hydrocarbon group. R in the polycarbonate polyol may be a combination of branched and linear R, or may be a single linear R.
The polycarbonate polyol may be used alone or in combination of 1 or more than 2.
As the polyisocyanate compound to be a raw material of the moisture-curable urethane resin, an aromatic polyisocyanate compound or an aliphatic polyisocyanate compound is suitably used.
Examples of the aromatic polyisocyanate compound include diphenylmethane diisocyanate, a liquid modified diphenylmethane diisocyanate, polymeric MDI, toluene diisocyanate, naphthalene-1, 5-diisocyanate, and the like.
Examples of the aliphatic polyisocyanate compound include 1, 6-hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate, trans-cyclohexane-1, 4-diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, cyclohexane diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, and the like.
Among them, aromatic polyisocyanate compounds are preferable from the viewpoint that the adhesive force after complete curing can be made high, and among them, diphenylmethane diisocyanate is more preferable. In addition, the aliphatic polyisocyanate compound is preferable from the viewpoint of easily imparting stress relaxation property, flexibility, and the like to the cured product of the photo moisture curable resin composition.
The polyisocyanate compound may be used alone or in combination of 2 or more.
(moisture-curable urethane resin having a polyester skeleton)
The moisture-curable urethane resin having a polyester skeleton is obtained by introducing the polyester skeleton into the urethane resin by using a polyester polyol as the polyol compound. The moisture-curable urethane resin having a polyester skeleton can be obtained by reacting a polyester polyol having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
Examples of the polyester polyol include a polyester polyol obtained by reacting a polycarboxylic acid with a polyol, a poly-epsilon-caprolactone polyol obtained by ring-opening polymerization of epsilon-caprolactone, and the like.
Examples of the polycarboxylic acid as a raw material of the polyester polyol include phthalic acid, terephthalic acid, isophthalic acid, 1, 5-naphthalenedicarboxylic acid, 2, 6-naphthalenedicarboxylic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, dodecanedicarboxylic acid, and the like. Among them, phthalic acid or adipic acid is preferable from the viewpoint of easier improvement of the adhesion at high temperature.
Examples of the polyhydric alcohol used as a raw material of the polyester polyol include ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 4-butanediol, neopentyl glycol, 1, 5-pentanediol, 1, 6-hexanediol, diethylene glycol, and cyclohexanediol. Among them, 1, 6-hexanediol or 1, 4-butanediol is preferable from the viewpoint of easier improvement of adhesion at high temperature.
Further, as the polyisocyanate compound, the above polyisocyanate compound may be used.
The polyester polyol may be used alone or in combination of 1 or more than 2.
(moisture-curable urethane resin having polyether skeleton)
The moisture-curable urethane resin having a polyether skeleton is obtained by introducing a polyether skeleton into a urethane resin by using a polyether polyol as the polyol compound. The urethane resin having a polyether skeleton can be obtained by reacting a polyether polyol having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
Examples of the polyether polyol include polyethylene glycol, polypropylene glycol, a ring-opening polymer of tetrahydrofuran, a ring-opening polymer of 3-methyltetrahydrofuran, a random copolymer or a block copolymer of these or a derivative thereof, and a bisphenol-type polyoxyalkylene modified body.
Here, the bisphenol-type polyoxyalkylene modified body is a polyether polyol obtained by addition reaction of an alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.) with an active hydrogen moiety of a bisphenol-type molecular skeleton. The polyether polyol may be a random copolymer or a block copolymer. The above-mentioned bisphenol-type polyoxyalkylene modified body is preferably obtained by adding 1 or 2 or more kinds of alkylene oxides to both ends of a bisphenol-type molecular skeleton.
The bisphenol type is not particularly limited, and examples thereof include type a, type F, type S, and the like, and bisphenol a type is preferable.
Further, as the polyisocyanate compound, the above polyisocyanate compound may be used.
The moisture-curable urethane resin having a polyether skeleton preferably further contains a substance obtained by using a polyol compound having a structure represented by the following formula (2). By using the polyol compound having a structure represented by the following formula (2), a photo-moisture-curable resin composition excellent in adhesion and a cured product excellent in flexibility and elongation can be obtained, and compatibility with the radical-polymerizable compound (a) is excellent.
Among them, from the viewpoint of easily improving the coatability by making the viscosity of the photo moisture curable resin composition in a proper range, a polyether polyol composed of a ring-opening polymerization compound of polypropylene glycol, tetrahydrofuran (THF), or a ring-opening polymerization compound of tetrahydrofuran having a substituent such as methyl group, such as 3-methyltetrahydrofuran, is preferably used, and a ring-opening polymerization compound of polypropylene glycol and Tetrahydrofuran (THF) is more preferably used. The ring-opening polymerization compound of Tetrahydrofuran (THF) compound is generally polytetramethylene ether glycol.
The polyether polyol may be used alone or in combination of 1 or more than 2.
In formula (2), R represents a hydrogen atom, a methyl group, or an ethyl group, l is an integer of 0 to 5, m is an integer of 1 to 500, and n is an integer of 1 to 10. l is preferably 0 to 4, m is preferably 50 to 200, and n is preferably 1 to 5. The case where l is 0 is a case where carbon bonded to R is directly bonded to oxygen.
Among the above, the total of n and l is more preferably 1 or more, and still more preferably 1 to 3. R is more preferably a hydrogen atom or a methyl group, and particularly preferably a methyl group.
The moisture-curable urethane resin having a polycarbonate, polyester, or polyether skeleton may have 2 or more skeletons in the molecule, and for example, may have a polycarbonate skeleton and a polyester skeleton. In this case, as the polyol compound to be used as a raw material, a polycarbonate polyol and a polyester polyol are preferably used. Similarly, a moisture-curable urethane resin having a polyester skeleton and a polyether skeleton, or the like may be used.
The moisture-curable urethane resin is preferably an isocyanate group-containing substance as described above, but is not limited to an isocyanate group-containing substance, and may be a hydrolyzable silyl group-containing urethane resin as described in the following hydrolyzable silyl group-containing resin.
(hydrolyzable silyl group-containing resin)
The hydrolyzable silyl group-containing resin used in the present invention is cured by reacting the hydrolyzable silyl group in the molecule with moisture in the air or in the adherend.
The resin containing a hydrolyzable silyl group may have only 1 hydrolyzable silyl group per 1 molecule, or may have 2 or more hydrolyzable silyl groups. Among them, it is preferable that the molecule has hydrolyzable silyl groups at both ends of the main chain.
The hydrolyzable silyl group-containing resin does not contain an isocyanate group-containing substance.
The hydrolyzable silyl group is represented by the following formula (3).
-SiR 1 3-a X a (3)
In formula (3), R 1 Each independently is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or an OSiR group which may be substituted 2 3 (R 2 Each independently a hydrocarbon group having 1 to 20 carbon atoms). In formula (3), X is independently a hydroxyl group or a hydrolyzable group. Further, in the formula (3), a is an integer of 1 to 3.
The hydrolyzable group is not particularly limited and includes, for example, a halogen atom, an alkoxy group, an alkenyloxy group, an aryloxy group, an acyloxy group, a ketoxime ester group, an amino group, an amide group, an acid amide group, an aminooxy group, a mercapto group, and the like. Among them, halogen atom, alkoxy group, alkenyloxy group and acyloxy group are preferable from the viewpoint of high activity. Further, from the viewpoint of mild hydrolyzability and easy handling, an alkoxy group such as methoxy group or ethoxy group is more preferable, and methoxy group or ethoxy group is further preferable. Further, from the viewpoint of safety, it is preferable that the compounds which are released by the reaction are ethanol, acetone, ethoxy, and isopropoxy, respectively.
The hydroxyl group or the hydrolyzable group may be bonded to 1 silicon atom in the range of 1 to 3. In the case where the hydroxyl group or the hydrolyzable group is bonded to 1 silicon atom by 2 or more, these groups may be the same or different.
From the viewpoint of curability, a in the above formula (3) is preferably 2 or 3, and particularly preferably 3. Further, from the viewpoint of storage stability, a is preferably 2.
In addition, R in the above formula (3) 1 Examples thereof include alkyl groups such as methyl and ethyl groups, cycloalkyl groups such as cyclohexyl groups, aryl groups such as phenyl groups, aralkyl groups such as benzyl groups, trimethylsiloxy groups, chloromethyl groups, methoxymethyl groups, and the like. Among them, methyl is preferable.
Examples of the hydrolyzable silyl group include a methyldimethoxysilyl group, a trimethoxysilyl group, a triethoxysilyl group, a tris (2-propenyloxy) silyl group, a triacetoxysilyl group, a (chloromethyl) dimethoxysilyl group, a (chloromethyl) diethoxysilyl group, a (dichloromethyl) dimethoxysilyl group, a (1-chloroethyl) dimethoxysilyl group, a (methoxymethyl) diethoxysilyl group, a (ethoxymethyl) dimethoxysilyl group, a (1-methoxyethyl) dimethoxysilyl group, an (aminomethyl) dimethoxysilyl group, an (N, N-dimethylaminomethyl) dimethoxysilyl group, an (N, N-diethylaminomethyl) diethoxysilyl group, an (N- (2-aminoethyl) aminomethyl) dimethoxysilyl group, an (acetoxymethyl) diethoxysilyl group, and the like.
Examples of the resin containing a hydrolyzable silyl group include (meth) acrylic resins containing a hydrolyzable silyl group, organic polymers having a hydrolyzable silyl group at a molecular chain end or a molecular chain end position, and urethane resins containing a hydrolyzable silyl group.
The hydrolyzable silyl group-containing (meth) acrylic resin preferably has a repeating structural unit derived from a hydrolyzable silyl group-containing (meth) acrylate and/or an alkyl (meth) acrylate in the main chain.
Examples of the hydrolyzable silyl group-containing (meth) acrylate include 3- (trimethoxysilyl) propyl (meth) acrylate, 3- (triethoxysilyl) propyl (meth) acrylate, 3- (methyldimethoxysilyl) propyl (meth) acrylate, 2- (trimethoxysilyl) ethyl (meth) acrylate, 2- (triethoxysilyl) ethyl (meth) acrylate, 2- (methyldimethoxysilyl) ethyl (meth) acrylate, trimethoxysilylmethyl (meth) acrylate, triethoxysilylmethyl (meth) acrylate, and (methyldimethoxysilyl) methyl (meth) acrylate.
Examples of the alkyl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, n-heptyl (meth) acrylate, n-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-nonyl (meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate, stearyl (meth) acrylate, and the like.
Specific examples of the method for producing the hydrolyzable silyl group-containing (meth) acrylic resin include a method for synthesizing a hydrolyzable silyl group-containing (meth) acrylate polymer described in International publication No. 2016/035718.
The organic polymer having a hydrolyzable silyl group at a molecular chain end or a molecular chain end position has a hydrolyzable silyl group at least one of a terminal of a main chain and a terminal of a side chain.
The skeleton structure of the main chain is not particularly limited, and examples thereof include saturated hydrocarbon polymers, polyoxyalkylene polymers, and (meth) acrylate polymers.
Examples of the polyoxyalkylene polymer include polymers having a polyoxyethylene structure, a polyoxypropylene structure, a polyoxybutylene structure, a polyoxytetramethylene structure, a polyoxyethylene-polyoxypropylene copolymer structure, and a polyoxypropylene-polyoxybutylene copolymer structure.
Specific examples of the method for producing an organic polymer having a hydrolyzable silyl group at a molecular chain end or a molecular chain end region include a method for synthesizing an organic polymer having a crosslinkable silyl group only at a molecular chain end or a molecular chain end region described in International publication No. 2016/035718. Further, as another method for producing the organic polymer having a hydrolyzable silyl group at a molecular chain end or a molecular chain end portion, there is mentioned, for example, a method for synthesizing a reactive silicon group-containing polyoxyalkylene polymer described in International publication No. 2012/117902.
Examples of the method for producing the hydrolyzable silyl group-containing urethane resin include a method in which, when a polyol compound is reacted with a polyisocyanate compound to produce a urethane resin, a silyl group-containing compound such as a silane coupling agent is further reacted. Specifically, for example, a method of synthesizing a urethane oligomer having a hydrolyzable silyl group described in JP-A2017-48345 is mentioned.
Examples of the silane coupling agent include vinyltrichlorosilane, vinyltriethoxysilane, vinyltris (. Beta. -methoxy-ethoxy) silane, β - (3, 4-epoxycyclohexyl) -ethyltrimethoxysilane, γ -glycidoxypropyl trimethoxysilane, γ -glycidoxypropyl methyldiethoxysilane, γ -methacryloxypropyl trimethoxysilane, N- (. Beta. -aminoethyl) - γ -aminopropyl trimethyldimethoxysilane, N-phenyl-. Gamma. -aminopropyl trimethoxysilane, γ -chloropropyltrimethoxysilane, γ -mercaptopropyl trimethoxysilane, γ -aminopropyl trimethoxysilane, 3-isocyanatopropyl trimethoxysilane, and 3-isocyanatopropyl triethoxysilane. Among them, gamma-mercaptopropyl trimethoxysilane, 3-isocyanatopropyl triethoxysilane are preferable. These silane coupling agents may be used alone or in combination of 2 or more.
In addition, the moisture-curable urethane resin may have both an isocyanate group and a hydrolyzable silyl group. The moisture-curable urethane resin having both an isocyanate group and a hydrolyzable silyl group is preferably produced by first obtaining a moisture-curable urethane resin having an isocyanate group (raw urethane resin) by the above-described method, and further reacting a silane coupling agent with the raw urethane resin.
The moisture-curable urethane resin having an isocyanate group is as described above in detail. The silane coupling agent to be used for the reaction with the raw urethane resin may be selected from the above-listed materials as appropriate, but it is preferable to use a silane coupling agent having an amino group or a mercapto group from the viewpoint of reactivity with an isocyanate group. Specific preferable examples thereof include N- (. Beta. -aminoethyl) -gamma-aminopropyl trimethoxysilane, N- (. Beta. -aminoethyl) -gamma-aminopropyl trimethyldimethoxy silane, N-phenyl-. Gamma. -aminopropyl trimethoxysilane, gamma. -mercaptopropyl trimethoxysilane, gamma. -aminopropyl trimethoxysilane, and 3-isocyanatopropyl trimethoxysilane.
Further, the moisture-curable resin may have a radical polymerizable functional group. The radical polymerizable functional group that the moisture-curable resin may have is preferably a group having an unsaturated double bond, and particularly, a (meth) acryl group is more preferable in terms of reactivity. The moisture-curable resin having a radical-polymerizable functional group is not included in the radical-polymerizable compound, and is treated as the moisture-curable resin (B).
The moisture-curable resin (B) may be used singly or in combination of 1 kind or 2 or more kinds, selected from the above-mentioned various resins.
The weight average molecular weight of the moisture-curable resin (B) is preferably 7500 to 24000. When the weight average molecular weight is within the above range, the initial adhesion of the photo moisture curable resin composition can be easily increased. Further, the final heat-resistant adhesion is also easily improved by the upper limit value or less. From these viewpoints, the weight average molecular weight of the moisture-curable resin (B) is more preferably 7800 or more, still more preferably 10000 or more, still more preferably 11500 or more, still more preferably 20000 or less, still more preferably 16000 or less, still more preferably 15000 or less.
In the present specification, the weight average molecular weight is a value obtained by measuring by Gel Permeation Chromatography (GPC) and converting the weight average molecular weight into polystyrene.
The moisture-curable resin may be chain-extended so that the weight average molecular weight is equal to or higher than a predetermined value as described above.
For example, in the moisture-curable urethane resin, the chain extender may be further reacted with a urethane resin having an isocyanate group (hereinafter, also referred to as "raw material urethane resin") obtained by reacting a polyol compound with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule. In this case, the chain extender is preferably used in an amount appropriately adjusted so that the isocyanate groups remain in the moisture-curable urethane resin without reacting the chain extender with all the isocyanate groups of the raw urethane resin. The raw material urethane resin may be further reacted with a chain extender that reacts with the raw material urethane resin.
The chain extender used in the moisture-curable urethane resin is preferably a polyol compound. The details of the polyol compound are as described above. The polyol compound used as the chain extender may be the same as the polyol compound used for synthesizing the raw material urethane resin. Therefore, if the polyol compound used for synthesizing the raw material urethane resin is a polycarbonate polyol, the chain extender may be a polycarbonate polyol.
The amount of the chain extender used is, for example, 5 parts by mass or more and 40 parts by mass or less, preferably 10 parts by mass or more and 35 parts by mass or less, more preferably 15 parts by mass or more and 30 parts by mass or less, based on 100 parts by mass of the total amount of the raw material urethane resin and the chain extender.
In the photo moisture curable resin composition, the mass ratio (B/A) of the moisture curable resin (B) to the radical polymerizable compound (A) is preferably 30/70 or more and 90/10 or less, more preferably 40/60 or more and 80/20 or less, still more preferably 50/50 or more and 70/30 or less. When the mass ratio is within these ranges, photocurability and moisture curability can be imparted to the photo-moisture curable resin composition in a well-balanced manner, and both the initial adhesion and the final heat-resistant adhesion can be easily adjusted to the desired ranges.
The photo-moisture curable resin composition may contain, as the resin component, a resin component other than the radical polymerizable compound (a) and the moisture curable resin (B), for example, a resin component such as a thermoplastic resin having no curability (for example, an acrylic resin, a urethane resin, or the like), a thermosetting resin, or the like, as long as the effects of the present invention are not impaired. The proportion of the resin component other than the radical polymerizable compound (a) and the moisture-curable resin (B) is, for example, 50 parts by mass or less, preferably 30 parts by mass or less, and more preferably 10 parts by mass or less, relative to 100 parts by mass of the total amount of the radical polymerizable compound (a) and the moisture-curable resin (B).
[ photopolymerization initiator (C) ]
The photo moisture curable resin composition of the present invention contains a photopolymerization initiator. The photo-moisture curable resin composition suitably imparts photocurability by containing a photopolymerization initiator.
Examples of the photopolymerization initiator include benzophenone-based compounds, acetophenone-based compounds, alkylbenzene ketone-based photopolymerization initiators, acylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin ether-based compounds, thioxanthone, and the like.
Examples of commercial products among the photopolymerization initiators include IRGACURE184, IRGACURE369, IRGACURE379EG, IRGACURE651, IRGACURE784, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACURE OXE01, IRGACURE TPO (all manufactured by BASF), benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (all manufactured by Tokyo chemical industry Co., ltd.), and the like.
The content of the photopolymerization initiator in the photo moisture curable resin composition is preferably 0.1 part by mass or more and 10 parts by mass or less, more preferably 0.5 parts by mass or more and 5 parts by mass or less, based on 100 parts by mass of the radical polymerizable compound (a). When the content of the photopolymerization initiator is within these ranges, the obtained photo-moisture-curable resin composition is excellent in photo-curability and storage stability. Further, in the above range, the photoradical polymerizable compound is properly cured, and thus the adhesion is easily improved.
[ Compound (D) ]
The photo moisture curable resin composition of the present invention contains a compound (D) having 3 or more isocyanate groups in the molecule (hereinafter, sometimes simply referred to as compound (D)). The photo-moisture-curable resin composition contains the compound (D) to form a crosslinked structure in the moisture-cured product, and thus the bulk strength is increased, and the heat-resistant adhesive force (final heat-resistant adhesive force) after moisture curing is improved. Therefore, as described above, for example, even if the molecular weight of the moisture-curable resin (B) is increased, the bulk strength of the cured product is not lowered, and the final heat-resistant adhesive force can be made excellent.
The compound (D) may be any compound other than the moisture-curable resin (B) and has 3 or more isocyanate groups. The compound (D) is preferably a compound having a molecular weight (formula weight) of 1500 or less, for example. The compound (D) may be a polyisocyanate-modified product obtained by reacting a polyisocyanate compound with another compound.
Examples of the modified polyisocyanate include a biuret-modified polyisocyanate compound, an isocyanurate-modified polyisocyanate compound, a polyol-modified polyisocyanate compound obtained by reacting a polyisocyanate compound with glycerin, trimethylolpropane, or an adduct obtained by adding an alkylene oxide such as propylene oxide or ethylene oxide thereto, and a polymethylene polyphenyl polyisocyanate also called polymeric MDI.
At least a part of isocyanate groups contained in the compound (D) may be temporarily protected by a blocking agent, a uretdione structure, or the like. In this case, the isocyanate group contained in the compound (D) is regenerated by dissociation of the blocking agent, cleavage of the uretdione structure, or the like at the time of use of the photo moisture curable resin composition.
The polyisocyanate compound used as a raw material for the modified product includes monomers having no repeating unit. The polyisocyanate compound is preferably a diisocyanate compound, and specifically, aromatic isocyanates such as toluene diisocyanate, diphenylmethane diisocyanate (MDI), 1, 5-naphthalene diisocyanate, and aliphatic isocyanate compounds such as isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, hydrogenated MDI, norbornane diisocyanate, xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, tetramethylxylylene diisocyanate, and the like are exemplified.
Further, as the compound (D), a polyisocyanate compound other than the above polyisocyanate modified product, such as triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, and 1,6, 11-undecane triisocyanate, may be used.
Among the above, polyisocyanate modified products are preferable, and among them, isocyanurate modified products and polymeric MDI are more preferable.
Further, the compound (D) may have 3 or more isocyanate groups, but preferably contains a compound having 4 or more isocyanate groups, more preferably contains a compound having 5 or more isocyanate groups, in order to increase the crosslinking density and further improve the heat-resistant adhesion after moisture curing. The upper limit of the number of isocyanate groups of the compound (D) is not particularly limited, and is, for example, 10 or less, preferably 8 or less.
Among the above, the compound having 3 isocyanate groups includes biuret modified compounds, isocyanurate modified compounds, and polyol modified compounds, but isocyanurate modified compounds are preferred. Further, a suitable specific example of the compound having 4 or 5 or more isocyanate groups is polymeric MDI.
The compound (D) having 3 or more isocyanate groups may be a mixture of compounds having isocyanate groups different from each other in number, and therefore, the number of isocyanate groups of the compound (D) may be represented by an average number of isocyanate groups. The average isocyanate group of the compound (D) is 3 or more, but is preferably 4 or more, more preferably 5 or more, in order to further improve the heat-resistant adhesion.
The upper limit of the average isocyanate number of the compound (D) is not particularly limited, and is, for example, 10 or less, preferably 8 or less, and more preferably 6.5 or less.
The content of the compound (D) in the photo-moisture-curable resin composition is preferably 0.1 part by mass or more and 10 parts by mass or less relative to 100 parts by mass of the total of the radical-polymerizable compound (a) and the moisture-curable resin (B). If the lower limit is not less than the above-mentioned lower limit, the compound (D) can form a sufficient crosslinked structure in the cured product after moisture curing, and the final heat-resistant adhesive strength can be easily improved. Further, by being 10 parts by mass or less, the initial adhesion can be prevented from being lowered by the influence of the compound (D). From these viewpoints, the content of the compound (D) is preferably 0.2 parts by mass or more, more preferably 0.3 parts by mass or more, still more preferably 5 parts by mass or less, and still more preferably 3 parts by mass or less, relative to 100 parts by mass of the total of the radically polymerizable compound (a) and the moisture-curable resin (B).
The photo moisture curable resin composition may contain a diisocyanate compound having 2 isocyanate groups in addition to the compound (D) having 3 or more isocyanate groups in the molecule. Specific examples of the diisocyanate compound used herein include diisocyanate compounds listed as raw materials for the polyisocyanate modified product.
The polyisocyanate modified product may remain as an unreacted diisocyanate compound without reacting the diisocyanate compound as a raw material during the production thereof, but such an unreacted diisocyanate compound may be blended with the compound (D) in the photo moisture curable resin composition.
For example, polymethylene polyphenyl polyisocyanates having 3 or more isocyanate groups (polymeric MDI) may be compounded in the photo moisture curable resin composition in the form of a mixture with MDI as a diisocyanate compound.
The content of the diisocyanate compound in the photo moisture curable resin composition is not particularly limited, and for example, the content of the diisocyanate compound is preferably smaller than the content of the compound (D) on a mass basis.
[ Filler (E) ]
The photo moisture curable resin composition of the present invention may contain a filler (E). By containing the filler (E), the photo-moisture curable resin composition of the present invention has suitable thixotropic properties and can sufficiently maintain the shape after coating. As the filler, a particulate material may be used.
The filler (E) is preferably an inorganic filler, and examples thereof include silica, talc, titanium oxide, zinc oxide, and calcium carbonate. Among them, silica is preferable in view of excellent ultraviolet transmittance of the obtained photo moisture curable resin composition. The filler (E) may be subjected to hydrophobic surface treatments such as silylation, alkylation and epoxidation.
The filler (E) may be used alone or in combination of 1 or more than 2.
The content of the filler (E) is preferably 1 part by mass or more and 25 parts by mass or less, more preferably 2 parts by mass or more and 20 parts by mass or less, and still more preferably 3 parts by mass or more and 15 parts by mass or less, relative to 100 parts by mass of the total amount of the radical polymerizable compound (a) and the moisture curable resin (B).
(moisture curing acceleration catalyst)
The photo-moisture curable resin composition may contain a moisture curing accelerator catalyst that accelerates the moisture curing reaction of the moisture curable resin (B). By using the moisture curing accelerator, the photo-moisture curable resin composition is more excellent in moisture curability, and the adhesion is easily improved.
Specific examples of the moisture curing accelerator include amine-based compounds and metal-based catalysts. Examples of the amine compound include compounds having a morpholine skeleton such as di (methylmorpholino) diethyl ether, 4-morpholinopropylmorpholine and 2,2' -dimorpholino diethyl ether, dimethylamino-containing amine compounds having 2 dimethylamino groups such as bis (2-dimethylaminoethyl) ether and 1, 2-bis (dimethylamino) ethane, triethylamine, 1, 4-diazabicyclo [2.2.2] octane, 2,6, 7-trimethyl-1, 4-diazabicyclo [2.2.2] octane, and the like.
Examples of the metal catalyst include tin compounds such as di-n-butyltin dilaurate, di-n-butyltin diacetate and tin octoate, zinc compounds such as zinc octoate and zinc naphthenate, and other metal compounds such as zirconium tetraacetylacetonate, copper naphthenate and cobalt naphthenate.
The content of the moisture curing acceleration catalyst is preferably 0.01 part by mass or more and 8 parts by mass or less, more preferably 0.1 part by mass or more and 5 parts by mass or less, relative to 100 parts by mass of the moisture curable resin (B). The content of the moisture curing accelerator is within the above range, so that the effect of accelerating the moisture curing reaction is excellent without deteriorating the storage stability and the like of the photo-moisture curable resin composition.
(colorant)
The photo moisture curable resin composition of the present invention may contain a colorant. Examples of the colorant include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. The light-moisture curable resin composition also has excellent light-shielding properties and the like by containing a colorant. Among them, titanium black is preferred. The titanium black has a property of sufficiently shielding light having a wavelength in the visible light region and transmitting light having a wavelength in the vicinity of the ultraviolet region, and thus can prevent the photocurability of the photo-moisture curable resin composition from being lowered.
The content of the colorant in the photo-moisture-curable resin composition is preferably 0.05 parts by mass or more and 8 parts by mass or less, more preferably 0.1 parts by mass or more and 2 parts by mass or less, relative to 100 parts by mass of the total amount of the radical polymerizable compound (a) and the moisture-curable resin (B). When the content of the colorant is within these ranges, appropriate light-shielding properties can be imparted while maintaining good adhesion of the photo-moisture curable resin composition.
The photo moisture curable resin composition may contain other additives such as a coupling agent, wax particles, ionic liquid, expanded particles, and reactive diluents, in addition to the above-described components. The coupling agent may be a silane coupling agent, a titanate coupling agent, a zirconate coupling agent, or the like, but among them, a silane coupling agent is preferable. The photo moisture curable resin composition generally contains no solvent, but may contain a solvent as required within a range that does not impair the effects of the present invention.
[ viscosity at 25 ]
The photo moisture curable resin composition of the present invention preferably has a viscosity (hereinafter also referred to as "25 ℃ C. Viscosity") of 40 Pa.s to 600 Pa.s both inclusive, as measured using a cone-plate viscometer at 25 ℃ C. And 5.0 rpm.
The viscosity of the moisture-curable resin composition at 25℃is measured under high shear at 5.0rpm, and is not easily affected by the filler. Therefore, if the viscosity at 25 ℃ is 40pa·s or more, the low molecular weight component contained in the moisture-curable resin (B) or the like tends to be reduced, and the moisture-curable resin (B) or the like is less likely to bleed out to the interface after light irradiation, and initial adhesion is likely to be improved. That is, if the moisture-curable resin (B) or the like having a low molecular weight is less likely to bleed out to the interface after light irradiation, sliding is less likely to occur between the adhesive and the adherend, and the adhesive force is likely to be exhibited, so that the initial adhesive force is likely to be improved. In the present invention, the moisture-curable resin composition contains a large amount of high molecular weight components by increasing the viscosity at 25 ℃, and the content of the functional group having moisture-curability is liable to be reduced. As a result, although the block strength after moisture curing may be low, the block strength after moisture curing becomes high and the heat-resistant adhesion becomes good as a result by containing the compound (D).
Further, even if the viscosity at 25 ℃ is 600pa·s or less, the adhesiveness inherent to the moisture-curable resin (B) and the like are easily exhibited, and thus the initial adhesion and the final heat-resistant adhesion are easily improved.
Further, by setting the viscosity at 25 ℃ to 40pa·s or more and 600pa·s or less, problems such as occurrence of liquid dripping or failure to apply at normal temperature are less likely to occur, and workability is improved.
The viscosity of the photo-moisture curable resin composition at 25℃is more preferably 45 pas or more, still more preferably 90 pas or more, still more preferably 110 pas or more, still more preferably 500 pas or less, still more preferably 350 pas or less, still more preferably 230 pas or less. When the viscosity at 25℃is within the above range, the workability and initial adhesion can be easily improved.
Further, if the molecular weight of the moisture-curable resin (a) is not more than the upper limit, the initial adhesion is easily improved, and further, the adhesion is sufficiently improved by moisture curing, and the final heat-resistant adhesion and the like are easily improved.
[ internal/external ratio a/b ]
The photo moisture curable resin composition of the present invention is applied linearly to an aluminum substrate under predetermined conditions described later, and when the glass plate is further pressure-bonded after photo curing by UV, a/b (also referred to as "internal/external ratio a/b") is, for example, 0.5 to 0.99 when the average width of the bonded portion on the glass plate side is a and the average width of the bonded portion on the aluminum substrate side is b.
When the internal/external ratio a/b is 0.5 or more, the internal/external ratio a/b becomes large, and the resin composition of the present invention is liable to collapse immediately after photocuring, and the adhesion to the interface of the adherend becomes high, and the initial adhesion to the adherend is liable to become high. Further, by setting the internal/external ratio a/b to 0.99 or less, it is possible to prevent the initial adhesion from being lowered by reducing the cohesive force or excessively collapsing the photo-moisture curable resin composition immediately after photo-curing.
The internal/external ratio a/b is more preferably 0.58 or more, still more preferably 0.63 or more, still more preferably 0.7 or more, still more preferably 0.95 or less, still more preferably 0.93 or less. If the internal/external ratio a/b is within these ranges, the initial adhesion tends to be improved.
In the present invention, the internal/external ratio a/b is measured as follows. First, as shown in fig. 1 (a), a moisture curable resin composition 10 was applied to an aluminum substrate 11 at a line width of 1.0 mm. Here, the line width of 1.0mm is not necessarily strictly 1.0mm, and may be 1.0±0.1 mm. Next, as shown in FIG. 1 (b), the moisture-curable resin composition 10 was irradiated with 1000mJ/cm 2 The moisture-curable resin composition 10 is cured by ultraviolet rays of (a). Immediately (within 10 seconds), as shown in fig. 1 (c), the glass plate 12 was superimposed on the moisture-curable resin composition 10, and the coated area of the glass plate 12 on the moisture-curable resin composition 10 was pressure-bonded at 0.08MPa for 120 seconds. After the press-bonding, the width a1 of the bonded portion of the moisture-curable resin composition 10 with the glass plate 12 was measured. The width a1 was measured at 5 points, and the average value thereof was defined as the average width a. Further, the width b1 of the portion of the moisture-curable resin composition 10 bonded to the aluminum substrate 11 was measured. The width b1 was measured at 5 points, the average value thereof was defined as the average width b, and the internal/external ratio a/b was calculated from the average widths a and b. The pressure bonding is performed using a weight, and the widths a1 and b1 are preferably measured 5 minutes after the weight is removed.
The internal/external ratio a/b can be adjusted within the above range by adjusting the kind of the radical polymerizable compound and the like. For example, in the case where the photo moisture curable resin composition contains a monofunctional radical polymerizable compound in a large amount as a radical polymerizable compound, the proportion of the crosslinked structure formed after photo curing becomes small, and therefore the internal/external ratio a/b can be made large. In addition, for example, when the photo moisture curable resin composition contains a large amount of a radical polymerizable compound having a low glass transition temperature of a homopolymer as the radical polymerizable compound, the cured product after photo curing becomes soft, and thus the internal and external ratio a/b can be made larger. Further, the weight average molecular weight of the moisture-curable resin (B) may be adjusted.
[ adhesive force ]
The initial adhesion of the photo moisture curable resin composition of the present invention may be, for example, 0.05MPa or more, but is preferably 0.1MPa or more. In addition, the photo moisture curable resin composition of the present invention preferably has a final heat resistant adhesion of 1.0MPa or more.
The initial adhesion means adhesion at 25 ℃ immediately after the photo-moisture curable resin composition was photo-cured, and the final heat resistant adhesion means adhesion measured at 70 ℃ after the photo-moisture curable resin composition was photo-cured and then left at 25 ℃ for 24 hours at 50 RH%. The details of the method for measuring the initial adhesion and the final heat-resistant adhesion are as described in examples below.
If the initial adhesion at 25 ℃ is set to the above lower limit, the photo-moisture curable resin composition can temporarily adhere adherends to each other with a constant adhesion or more immediately after photo-curing, and the workability at the time of temporary adhesion can be improved. In addition, if the final heat-resistant adhesion is 1.0MPa or more, the adherends can be firmly bonded to each other by the primary adhesion by moisture curing after the temporary adhesion under a high-temperature environment.
In order to further improve the adhesion stability during temporary bonding, the photo moisture curable resin composition preferably has an initial adhesion of 0.2MPa or more. The initial adhesion is not particularly limited, but is preferably less than 1.5MPa for easy re-adhesion at the time of temporary adhesion, for example.
In addition, in order to more firmly bond adherends to each other after the main adhesion, the final heat-resistant adhesion of the photo moisture-curable resin composition is more preferably 2.0MPa or more. The higher the final heat-resistant adhesive strength is, the better, and is not particularly limited, and for example, 20MPa or less, and may be 10MPa or less.
Examples of the method for producing the photo-moisture curable resin composition of the present invention include a method in which the radical polymerizable compound (a), the moisture curable resin (B), the photopolymerization initiator (C), and the compound (D) are mixed with other additives such as a filler, a moisture curing accelerator, and a colorant, which are further mixed as needed, using a mixer. Examples of the mixer include a homogenizing and dispersing machine, a homogenizing and mixing machine, a universal mixer, a planetary stirring device, a kneader, and three rolls.
As described above, a moisture-curable resin such as a moisture-curable urethane resin may be increased in molecular weight by a chain extender. In this case, for example, a raw material resin such as a raw material urethane resin is reacted with a chain extender in advance to obtain a moisture-curable resin (B), and then, as described above, it is preferable to mix the moisture-curable resin (B) with other raw materials such as a radical polymerizable compound (a), a photopolymerization initiator (C), and a compound (D).
The moisture-curable resin (B) may be synthesized by mixing the raw material resin, the chain extender, and the radical-polymerizable compound (a), and heating the mixture as necessary to react the chain extender with the raw material resin. In this case, since a mixture of the moisture-curable resin (B) and the radical-polymerizable compound (a) is obtained, a photopolymerization initiator (C), a compound (D), and other additives further blended as necessary may be added to the mixture to obtain a photo moisture-curable resin composition.
Method for Using photo-moisture curable resin composition
The photo moisture curable resin composition of the present invention is cured and used as a cured product. Specifically, the photo-moisture curable resin composition of the present invention is preferably cured completely by curing it with moisture after being first photo-cured by light irradiation, for example, in a B-stage state (semi-cured state).
Here, when the photo-moisture curable resin composition is disposed between the adherends and the adherends are bonded to each other, it is preferable to apply the photo-moisture curable resin composition to one of the adherends, then to photo-cure the one of the adherends by irradiation with light, for example, to form a B-stage state, and to superimpose the other adherend on the photo-moisture curable resin composition in the cured state, so that the adherends are temporarily bonded to each other with a proper adhesive force (initial adhesive force). Then, the photo-moisture-curable resin composition in the B-stage state is cured by moisture, thereby completely curing, and the adherends superimposed via the photo-moisture-curable resin composition are bonded together with a sufficient adhesive force.
The application of the photo-moisture curable resin composition to an adherend is preferably performed, for example, by a dispensing device, and is not particularly limited. The light to be irradiated during the photo-curing is not particularly limited as long as it is a light to cure the radical polymerizable compound, but is preferably ultraviolet light. In addition, when the photo-moisture curable resin composition is completely cured by moisture after photo-curing, the composition may be left in the atmosphere for a predetermined time.
The application of the photo-moisture curable resin composition to an adherend is not particularly limited, but is preferably carried out at around normal temperature, more specifically, at a temperature of about 10 to 35 ℃. The photo moisture curable resin composition of the present invention has a viscosity of 25 ℃ within the above-specified range, so that even when it is applied at around normal temperature, it can be easily applied and no liquid dripping occurs.
Further, the photo moisture curable resin composition of the present invention exhibits an initial adhesion force of a certain value or more immediately after light irradiation, and thus can be temporarily adhered immediately after light curing, resulting in good workability.
The photo moisture curable resin composition of the present invention is preferably used as an adhesive for electronic parts. That is, the present invention also provides an adhesive for electronic parts comprising the above photo-moisture curable resin composition.
Therefore, the adherend is preferably various electronic components constituting an electronic device. Examples of the various electronic components constituting the electronic device include various electronic components provided on a display element and constituting an electronic circuit, a substrate on which the electronic components are mounted, a case constituting the electronic device, and a semiconductor chip.
The material of the adherend may be any of metal, glass, plastic, and the like. Further, the shape of the adherend is not particularly limited, and examples thereof include a film shape, a sheet shape, a plate shape, a panel shape, a disc shape, a rod (stick shape), a box shape, a case shape, and the like.
As described above, the photo moisture curable resin composition of the present invention is preferably used for bonding electronic components constituting an electronic device to each other. The photo-moisture curable resin composition of the present invention is preferably used also for joining electronic parts to other parts. With these configurations, the electronic component has the cured body of the present invention.
The photo-moisture curable resin composition of the present invention is used in electronic devices, for example, to obtain an assembled component by bonding substrates to each other. The assembled component thus obtained has a 1 st substrate, a 2 nd substrate, and the cured body of the present invention, and at least a part of the 1 st substrate is bonded to at least a part of the 2 nd substrate via the cured body. The 1 st substrate and the 2 nd substrate are preferably each mounted with at least 1 electronic component constituting an electronic circuit.
The photo moisture curable resin composition of the present invention is preferably used for narrow frame applications. For example, for various display devices such as display devices for mobile phones such as smart phones, it is preferable to use the photo moisture curable resin composition of the present invention as an adhesive by applying the adhesive to a base having a rectangular frame shape with a narrow width (i.e., a narrow frame) and assembling a display panel, a touch panel, or the like via the adhesive. Further, the photo moisture curable resin composition of the present invention is preferably used in semiconductor chip applications. The photo moisture curable resin composition of the present invention is used in the application of semiconductor chips, for example, for bonding semiconductor chips to each other.
Examples
The present invention will be described in further detail with reference to examples, but the present invention is not limited to these examples.
The physical properties were measured and evaluated as follows.
(weight average molecular weight)
The weight average molecular weight of the moisture curable resin (B) in each of examples and comparative examples was measured by Gel Permeation Chromatography (GPC), and was obtained by conversion to polystyrene. GPC measurement used Shodex KF-806L (manufactured by Showa Denko Co., ltd.) as a column. Further, tetrahydrofuran (THF) was used as a solvent and a mobile phase. Further, the measurement conditions for GPC were a flow rate of 1.0 ml/min and a measurement temperature of 40 ℃.
In each of examples and comparative examples, the weight average molecular weight was measured using a mixture of the radical polymerizable compound (a) and the moisture curable resin (B) as a sample. Since the peak of the radical polymerizable compound (a) appears on the low molecular weight side and the peak of the moisture curable resin (B) appears on the high molecular weight side of the mixture, the weight average molecular weight of the moisture curable resin (B) can be obtained from the peak on the high molecular weight side.
(internal-external ratio a/b)
The internal/external ratio a/b was measured by the method described in the specification. Aluminum alloy "a6063S" having dimensions of 2mm×25mm×60mm and a glass plate having a smooth surface, which was subjected to ultrasonic washing for 5 minutes, were used as the aluminum substrate and the glass plate, respectively. The moisture-curable resin composition was applied to an aluminum substrate linearly at room temperature (25 ℃) using Wu n (r) as a dispensing device, with a width of 1.0.+ -. 0.1mm, a length of 25mm, and a thickness of 0.4.+ -. 0.1 mm. Next, the coated photo-moisture curable resin composition was irradiated with ultraviolet light having a wavelength of 405nm at 1000mW by a linear LED irradiator (manufactured by HOYA Co., ltd.) 1000mJ/cm 2 And (5) irradiating. The glass plate was pressed against the aluminum substrate using a weight as a weight, and the widths a1 and b1 were measured 5 minutes after the weight was removed. The widths a1 and b1 after the press-bonding were measured by observing the press-bonding surface from the glass plate side using a microscope.
(viscosity at 25 ℃ C.)
The viscosity at 25℃was measured using a cone-plate viscometer (trade name: TVE-35, manufactured by Dong machine Co., ltd.) at 5.0rpm and at 25 ℃.
(initial adhesive force)
As shown in fig. 2 (a) and (b), the photo moisture curable resin composition 20 was applied to the aluminum substrate 21 at room temperature (25 ℃) using the above-mentioned dispensing apparatus so that the width became 1.0±0.1mm, the length became 25mm, and the thickness became 0.4±0.1 mm. Further, ultraviolet rays having a wavelength of 405nm were irradiated with a linear LED irradiator (manufactured by HOYA Co., ltd.) at 1000mJ/cm and 1000mW 2 Irradiation is performed to thereby perform photocuring. Then, the glass plate 22 and the aluminum substrate 21 were bonded via the photo-cured photo-moisture-curable resin composition 20, and the sample 23 for evaluating adhesion was obtained by press-bonding with a weight at 0.08MPa for 120 seconds.
Then, the aluminum substrate 21 was stretched at a speed of 10 mm/min in the shearing direction S by using a tensile tester ("tensile compression tester SVZ-50NB", manufactured by Kogyo Co., ltd.) under an atmosphere of 25℃to measure the maximum stress at the time of peeling off the aluminum substrate 21 from the glass plate 22, and the maximum stress was set as the initial adhesion. The time period from the completion of the photo-curing to the start of the tensile test was 150 seconds or less. The initial adhesion was evaluated by the following evaluation criteria.
A:0.2MPa or more
B:0.1MPa or more and less than 0.2MPa
C: less than 0.1MPa
(final heat-resistant adhesive force)
The glass plate and the aluminum substrate are bonded via the photo-moisture curable resin composition cured by light in the same manner as the initial adhesive force. Then, the mixture was left at 25℃for 24 hours at 50RH% to be moisture-cured, and a sample for evaluating adhesiveness was obtained. The sample for evaluating the adhesion was stretched in the shearing direction in the same manner as in the method for measuring the initial adhesion except that the atmospheric temperature was changed from 25 to 70 ℃, and the maximum stress at the time of peeling the aluminum substrate from the glass plate was measured to obtain the final heat-resistant adhesion.
A:2.0MPa or more
B:1.0MPa or more and less than 2.0MPa
C: less than 1.0MPa
The urethane resin raw materials used in the examples and comparative examples were produced by the following methods.
Synthesis example 1
(PC urethane resin raw material)
100 parts by mass of a polycarbonate diol (a compound represented by the formula (1), 90 mol% of R being 3-methylpentylene, 10 mol% being 1, 6-hexylene, manufactured by KarayLo Co., ltd., trade name "Kuraraypolyol C-1090"), and 0.01 parts by mass of dibutyltin dilaurate as a polyol compound were charged into a 500 mL-capacity separable flask. The flask was stirred at 100℃for 30 minutes under vacuum (20 mmHg or less) to mix the materials. Then, 50 parts by mass of diphenylmethane diisocyanate (trade name "Pure MDI" manufactured by soh corporation) was added as a polyisocyanate compound at normal pressure, and the mixture was stirred at 80℃for 3 hours to react the mixture, thereby obtaining a moisture-curable urethane resin (PC urethane resin raw material) having a polycarbonate skeleton and isocyanate groups at both ends. The weight average molecular weight of the obtained urethane resin raw material was 6700.
Synthesis example 2
(ET urethane resin raw material)
100 parts by mass of polytetramethylene ether glycol (trade name "PTMG-3000" manufactured by Mitsubishi chemical corporation) and 0.01 parts by mass of dibutyltin dilaurate as the polyol compound were charged into a 500-mL-capacity separable flask. The flask was stirred at 100℃for 30 minutes under vacuum (20 mmHg or less) to mix the materials. Then, 17.5 parts by mass of diphenylmethane diisocyanate (trade name "Pure MDI" manufactured by soh corporation) was added as a polyisocyanate compound at normal pressure, and the mixture was stirred at 80 ℃ for 3 hours to react the mixture, thereby obtaining a moisture-curable urethane resin (ET urethane resin raw material) having a polyether skeleton and isocyanate groups at both ends. The weight average molecular weight of the obtained urethane resin raw material was 3500.
Example 1
As shown in Table 5, each raw material constituting 60 parts by mass of the moisture-curable resin (PC-L25) was added to 40 parts by mass of the acrylic B. The acrylic B was obtained by mixing the respective compounds in the mixing ratios shown in Table 2. As a moisture-curable resin (PC-L25), a PC urethane resin raw material and a PC polyol were sequentially added to the acrylic B at the mass ratio shown in Table 3, to obtain a mixture. As the PC polyol, the polycarbonate diol used in synthesis example 1 was used.
The resultant mixture was stirred at 50 ℃ to thereby react a PC polyol with a part of the urethane resin raw material to synthesize a moisture-curable urethane resin which was chain-extended and has isocyanate groups at both ends, thereby obtaining a mixture of an acrylic B (radical-polymerizable compound) and a moisture-curable urethane resin.
To the mixture of the obtained acrylic B and moisture-curable urethane resin, the polyfunctional isocyanate a, photopolymerization initiator, and filler were further added and mixed according to the compounding in table 5, to obtain a photo moisture-curable resin composition. With respect to the obtained photo moisture curable resin composition, the viscosity at 25℃and the internal/external ratio a/b, the initial adhesion, and the final heat resistant adhesion were measured.
Examples 2, 3 and 5
The same procedure as in example 1 was carried out except that the polyfunctional isocyanate b was used instead of the polyfunctional isocyanate a and the blending amount was changed as shown in table 5.
Example 4
A photo-moisture curable resin composition was obtained in the same manner as in example 3 except that the polyfunctional isocyanate B, the photopolymerization initiator, the filler, and the colorant were added and mixed in the mixture of the acrylic B and the moisture curable urethane resin as shown in table 5.
Example 6
The same procedure as in example 3 was conducted except that the moisture-curable resin (ET-L25) was used instead of the moisture-curable resin (PC-L25) as shown in tables 4 and 5. That is, the procedure of example 3 was carried out except that the mixing ratio and types of the urethane resin raw material and the polyol added to the acrylic B were changed as shown in table 4, and a mixture of the acrylic B and the moisture-curable urethane resin was obtained. The ET polyol in table 4 was polytetramethylene ether glycol used in synthesis example 2.
Examples 7, 8 and 9
An acrylic C, D, A was used instead of the acrylic B, and the same procedure as in example 3 was carried out except that the acrylic B was used. The acrylic C, D, A was obtained by mixing the respective compounds in the mixing ratios shown in table 2.
Comparative examples 1 to 5
The same procedure as in examples 1 and 6 to 9 was conducted except that the polyfunctional isocyanates were not blended in comparative examples 1 to 5.
Comparative example 6
The same procedure as in example 1 was conducted except that 2-functional isocyanate (MDI) was used instead of the polyfunctional isocyanate.
Comparative example 7
The same procedure as in example 6 was conducted except that 2-functional isocyanate (MDI) was used instead of the polyfunctional isocyanate.
TABLE 1
| Trade name | Selling merchant | Name of the Compound | |
| Cyclic nitrogen-containing compound | NVC | Tokyo chemical industry (strain) | N-vinyl-epsilon-caprolactam |
| Monofunctional urethane acrylates | Pras コ part #216 | Osaka organic chemical industry (strain) | 1, 2-ethanediol 1-acrylic acid ester 2- (N-butylcarbamate) |
| Multifunctional urethane acrylates | EBECRYL8411 | The device can use the cover to gain the cover, and the cover is made of the cover | - |
| Monofunctional acrylate a | Pras コ port #192 | Osaka organic chemical industry (strain) | Phenoxy ethyl acrylate |
| Monofunctional acrylate b | IDAA | Osaka organic chemical industry (strain) | Isodecyl acrylate |
| Monofunctional acrylate c | DMAA | KJ chemical (strain) | Dimethylacrylamide |
| Monofunctional acrylate d | DEAA | KJ chemical (strain) | Diethyl acrylamide |
| Polyfunctional isocyanates a | コ II space HX | Chinese patent medicine "Jiuyi | Polyisocyanate modifier |
| Polyfunctional isocyanates b | And m-200 | Chinese patent medicine "Jiuyi | Polymethylene polyphenyl polyisocyanate |
| 2 functional isocyanate (MDI) | And a bit MT | Chinese patent medicine "Jiuyi | Diphenylmethane diisocyanate |
| Photopolymerization initiator | Irgacure TPO | BASF society | Diphenyl (2, 4, 6-trimethylbenzoyl) phosphine oxide |
| Filler (B) | AEROSIL RY-200S | Access by japan workers (strain) | Silica filler |
| Coloring agent | 13M-C | Mitsui (strain) | Titanium black |
The polyfunctional isocyanate a is an isocyanurate modified compound having 3 isocyanate groups in the molecule.
The polyfunctional isocyanate b was a mixture of MDI (2-functional isocyanate) and polymeric MDI (polymethylene polyphenyl polyisocyanate: compound (D)) having 3 or more isocyanate groups, the proportion of MDI was 40 mass%, and the proportion of polymeric MDI was 60 mass%. The average isocyanate number of the polymeric MDI is from 5 to 6.
Acrylic acid series a to D used in examples and comparative examples are as follows.
TABLE 2
The moisture curable resins (B) used in the examples and comparative examples are shown in tables 3 and 4 below. As described above, the following reaction product of the urethane resin raw material and the polyol was used as the moisture-curable resin (B).
TABLE 3
TABLE 4
TABLE 5
The photo-moisture curable resin compositions of examples 1 to 9 contain a compound (D) having 3 or more isocyanate groups in the molecule in addition to the radical polymerizable compound (a), the moisture curable resin (B) and the photopolymerization initiator (C), and thus the final heat resistant adhesive force after moisture curing is high, and high adhesive force can be maintained even in a high temperature environment.
In contrast, the photo-moisture curable resin compositions of comparative examples 1 to 5 do not contain the compound (D) having 3 or more isocyanate groups in the molecule, and therefore the final heat resistant adhesive force after moisture curing becomes low, and high adhesive force cannot be ensured under high temperature environments. This tendency is similar to that of comparative examples 6 and 7 in which a diisocyanate compound was used instead of the compound (D) having 3 or more isocyanate groups.
Claims (12)
1. A photo-moisture-curable resin composition comprising a radical-polymerizable compound (A), a moisture-curable resin (B), a photopolymerization initiator (C), and a compound (D) having 3 or more isocyanate groups in the molecule.
2. The photo-moisture curable resin composition according to claim 1, wherein the compound (D) comprises a compound having 5 or more isocyanate groups in a molecule.
3. The photo-moisture curable resin composition according to claim 1 or 2, which is applied to an aluminum substrate at a line width of 1.0mm and irradiated with 1000mJ/cm 2 In a state where the ultraviolet ray of (2) is cured by light, when the glass plate is pressure-bonded at 0.08MPa for 120 seconds, the glass plate side is bondedThe average width of the portion is a, and the average width of the bonding portion on the aluminum substrate side is b, the a/b is 0.5 to 0.99.
4. The photo-moisture curable resin composition according to any one of claims 1 to 3, having a viscosity of 40 Pa-s to 600 Pa-s, measured at 25 ℃ and 5.0rpm using a cone-plate viscometer.
5. The photo-moisture curable resin composition according to any one of claims 1 to 4, wherein the moisture curable resin (B) comprises a moisture curable urethane resin.
6. The photo-moisture curable resin composition according to any one of claims 1 to 5, wherein the weight average molecular weight of the moisture curable resin (B) is 7500 or more and 24000 or less.
7. The photo moisture-curable resin composition according to any one of claims 1 to 6, wherein the radical polymerizable compound (a) comprises a monofunctional radical polymerizable compound.
8. The photo-moisture curable resin composition according to claim 7, comprising 90 parts by mass or more of the monofunctional radical polymerizable compound per 100 parts by mass of the radical polymerizable compound (a).
9. The photo moisture-curable resin composition according to any one of claims 1 to 8, further comprising a filler (E).
10. An adhesive for electronic parts, which is composed of the photo moisture curable resin composition according to any one of claims 1 to 9.
11. A cured body of the photo moisture curable resin composition of any one of claims 1 to 10.
12. An electronic component comprising the cured body according to claim 11.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021-096073 | 2021-06-08 | ||
| JP2021096073 | 2021-06-08 | ||
| PCT/JP2022/023015 WO2022260053A1 (en) | 2021-06-08 | 2022-06-07 | Photo/moisture-curable resin composition, adhesive for electronic components, cured body, and electronic component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117480194A true CN117480194A (en) | 2024-01-30 |
Family
ID=84425985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202280040313.2A Pending CN117480194A (en) | 2021-06-08 | 2022-06-07 | Photo-moisture curable resin composition, adhesive for electronic component, cured body, and electronic component |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPWO2022260053A1 (en) |
| KR (1) | KR20240018465A (en) |
| CN (1) | CN117480194A (en) |
| TW (1) | TW202313708A (en) |
| WO (1) | WO2022260053A1 (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150111567A (en) | 2014-03-26 | 2015-10-06 | 대우조선해양 주식회사 | Power supply system |
| JP6510789B2 (en) * | 2014-10-03 | 2019-05-08 | 積水化学工業株式会社 | Moisture curable resin composition |
| JP6797420B2 (en) * | 2018-05-23 | 2020-12-09 | サンユレック株式会社 | Light moisture curable resin composition |
| JP2020147687A (en) * | 2019-03-14 | 2020-09-17 | Dic株式会社 | Urethane resin composition, adhesive, and floor structure |
-
2022
- 2022-06-07 KR KR1020237041958A patent/KR20240018465A/en unknown
- 2022-06-07 JP JP2022543049A patent/JPWO2022260053A1/ja active Pending
- 2022-06-07 CN CN202280040313.2A patent/CN117480194A/en active Pending
- 2022-06-07 WO PCT/JP2022/023015 patent/WO2022260053A1/en active Application Filing
- 2022-06-08 TW TW111121250A patent/TW202313708A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW202313708A (en) | 2023-04-01 |
| WO2022260053A1 (en) | 2022-12-15 |
| JPWO2022260053A1 (en) | 2022-12-15 |
| KR20240018465A (en) | 2024-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6641255B2 (en) | Adhesives for electronic components and adhesives for display elements | |
| CN115151578B (en) | Photo-moisture curable resin composition, adhesive for electronic component, cured body, and electronic component | |
| KR20170013852A (en) | Light/moisture-curable resin composition, adhesive for electronic components, and adhesive for display elements | |
| CN113302249B (en) | Photo-moisture curable resin composition and cured body | |
| JP6510788B2 (en) | Light moisture curable resin composition | |
| CN113286859B (en) | Curable resin composition and cured body | |
| CN117480194A (en) | Photo-moisture curable resin composition, adhesive for electronic component, cured body, and electronic component | |
| CN112673031B (en) | Curable resin composition and cured body | |
| KR20180089280A (en) | Light/moisture curable resin composition, adhesive agent for electronic parts, and adhesive agent for display elements | |
| CN115151577A (en) | Light-moisture-curable resin composition and cured body | |
| KR20220016023A (en) | Curable resin composition, cured product, and electronic component | |
| WO2023153514A1 (en) | Photo/moisture-curable resin composition, adhesive for electronic component, and adhesive for display element | |
| JP2020045403A (en) | Curable resin composition, cured product, electronic component, and assembly component | |
| WO2023176795A1 (en) | Light-moisture curable resin composition, adhesive agent for electronic component, and adhesive agent for display element | |
| WO2019203277A1 (en) | Curable resin composition, cured body, electronic part and assembly part | |
| KR102665572B1 (en) | Curable resin compositions, cured bodies, electronic components and assembly parts | |
| WO2024009957A1 (en) | Light/moisture curable resin composition, cured product, use of light/moisture curable resin composition, and end face protection method | |
| CN116568760A (en) | Moisture-curable resin composition and adhesive for electronic device | |
| TW202411369A (en) | Light- and moisture-curable resin compositions, cured products, uses of light- and moisture-curable resin compositions, and end-face protection methods | |
| CN116724096A (en) | Adhesive composition, adhesive for electronic component, and adhesive for portable electronic device | |
| KR20190077243A (en) | Moisture setting type resin composition and assembly parts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |