CN118369393A - Adhesive composition, adhesive for electronic component, and adhesive for portable electronic device - Google Patents
Adhesive composition, adhesive for electronic component, and adhesive for portable electronic device Download PDFInfo
- Publication number
- CN118369393A CN118369393A CN202280081800.3A CN202280081800A CN118369393A CN 118369393 A CN118369393 A CN 118369393A CN 202280081800 A CN202280081800 A CN 202280081800A CN 118369393 A CN118369393 A CN 118369393A
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- CN
- China
- Prior art keywords
- meth
- moisture
- adhesive composition
- acrylate
- group
- 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.)
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- 239000000853 adhesive Substances 0.000 title claims abstract description 167
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 167
- 239000000203 mixture Substances 0.000 title claims abstract description 145
- 239000011347 resin Substances 0.000 claims abstract description 84
- 229920005989 resin Polymers 0.000 claims abstract description 84
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims description 103
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 60
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 36
- 239000004417 polycarbonate Substances 0.000 claims description 23
- 229920000515 polycarbonate Polymers 0.000 claims description 23
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 18
- 229920000570 polyether Polymers 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 11
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 95
- -1 oxime ester Chemical class 0.000 description 73
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 51
- 239000000758 substrate Substances 0.000 description 44
- 229920005862 polyol Polymers 0.000 description 33
- 239000005056 polyisocyanate Substances 0.000 description 28
- 229920001228 polyisocyanate Polymers 0.000 description 28
- 125000001931 aliphatic group Chemical group 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 150000003254 radicals Chemical class 0.000 description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 150000002430 hydrocarbons Chemical group 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- 150000003077 polyols Chemical class 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 238000013008 moisture curing Methods 0.000 description 11
- 229930195734 saturated hydrocarbon Natural products 0.000 description 11
- 239000000945 filler Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000011342 resin composition Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 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 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 229920005906 polyester polyol Polymers 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- 150000003852 triazoles Chemical group 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007769 metal material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 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 3
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-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 group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 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
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 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
- 229920001400 block copolymer Polymers 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical compound [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 238000002156 mixing Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- 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
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-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
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- 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 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-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
- 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
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 1
- YKLJXSCAOKQNCN-UHFFFAOYSA-N 2-(2-isocyanatoethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCN=C=O YKLJXSCAOKQNCN-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 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 1
- KMFRQYRLHPRIOX-UHFFFAOYSA-N cyclopentane;isocyanic acid Chemical compound N=C=O.C1CCCC1 KMFRQYRLHPRIOX-UHFFFAOYSA-N 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 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
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 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
- 230000000694 effects Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-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
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- SEIUOYFQDIJJEO-UHFFFAOYSA-N hexane-1,1,1-tricarboxylic acid Chemical compound CCCCCC(C(O)=O)(C(O)=O)C(O)=O SEIUOYFQDIJJEO-UHFFFAOYSA-N 0.000 description 1
- KPYCPQVKYYJPIY-UHFFFAOYSA-N hexane;isocyanic acid Chemical compound N=C=O.CCCCCC KPYCPQVKYYJPIY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- DJFNMTSCKHMHQI-UHFFFAOYSA-N isocyanic acid;octane Chemical compound N=C=O.CCCCCCCC DJFNMTSCKHMHQI-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 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
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 239000011369 resultant mixture Substances 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
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
An adhesive composition comprising a moisture-curable resin and a silane coupling agent having a nitrogen-containing heterocyclic ring.
Description
Technical Field
The invention relates to an adhesive composition, an adhesive for electronic components, and an adhesive for portable electronic devices.
Background
Conventionally, a moisture-curable adhesive containing a moisture-curable resin cured by external moisture has been widely used, and is widely used in, for example, electronic devices. As the moisture curable adhesive, for example, patent document 1 discloses that a photo moisture curable resin composition containing a radical polymerizable compound, a moisture curable urethane resin, a photo radical polymerization initiator, and a coupling agent is obtained, which is excellent in adhesion and reliability under a high temperature environment and a high temperature and high humidity environment.
Patent document 2 discloses that a photo-moisture curable resin composition containing a radical polymerizable compound, a moisture curable resin, a photo-radical polymerization initiator, and a coupling agent is obtained, and that the photo-moisture curable resin composition is excellent in moist heat resistance.
Prior art literature
Patent literature
Patent document 1: international publication No. 2015/190499
Patent document 2: international publication No. 2017/094831
Disclosure of Invention
Problems to be solved by the invention
In recent years, however, portable electronic devices such as mobile phones including smart phones and tablet personal computers have been widely used as electronic devices. In addition, as portable electronic devices, wearable terminals are also becoming popular. As the electronic device, a metal is often used as a constituent member, and the metal material or the metal material and the resin material are often bonded to each other with an adhesive.
However, conventional moisture-curable adhesives cannot exhibit sufficient impact resistance, for example, when a metal material is an adherend. Therefore, for example, when a portable electronic device is dropped, there is a problem that the metal material peels off from other adherends due to impact during the dropping, which causes breakage of the portable electronic device, and the like.
Accordingly, the present invention has an object to provide a moisture-curable adhesive having sufficient impact resistance even when a metal is used as an adherend.
Means for solving the problems
The present inventors have conducted intensive studies and as a result, have found that the above problems are solved by an adhesive composition comprising a moisture-curable resin and a silane coupling agent having a nitrogen-containing heterocycle, and have completed the present invention.
The present invention provides the following [1] to [19].
[1] An adhesive composition comprising a moisture-curable resin and a silane coupling agent having a nitrogen-containing heterocycle.
[2] The adhesive composition according to [1], wherein the silane coupling agent has at least one of a triazole skeleton and a triazine skeleton.
[3] The adhesive composition according to [1] or [2], wherein the content of the silane coupling agent is 0.1 part by mass or more and 5 parts by mass or less relative to 100 parts by mass of the adhesive composition.
[4] The adhesive composition according to any one of [1] to [3], wherein the moisture-curable resin comprises at least 1 selected from the group consisting of a moisture-curable resin having a polyether skeleton, a moisture-curable resin having a polycarbonate skeleton, and a moisture-curable resin having a polyester skeleton.
[5] The adhesive composition according to any one of [1] to [4], wherein the moisture-curable resin comprises an isocyanate group-containing resin having an isocyanate group in a molecule.
[6] The adhesive composition according to [5], wherein the moisture-curable resin comprises an isocyanate group-containing resin having an isocyanate group and a (meth) acryloyl group in a molecule.
[7] The adhesive composition according to any one of [1] to [6], wherein the adhesive composition further comprises a radical polymerizable compound and a photopolymerization initiator.
[8] The adhesive composition according to [7], wherein the radically polymerizable compound comprises an aliphatic urethane (meth) acrylate.
[9] The adhesive composition according to [7] or [8], wherein the content of the radical polymerizable compound is 4 parts by mass or more and 59 parts by mass or less relative to 100 parts by mass of the adhesive composition.
[10] The adhesive composition according to any one of [7] to [9], wherein the content ratio of the radical polymerizable compound to the moisture-curable resin in the adhesive composition is 1/10 or more and 15/10 or less.
[11] The adhesive composition according to any one of [7] to [10], wherein the photopolymerization initiator is at least 1 selected from the group consisting of a benzophenone-based compound, an acetophenone-based compound, an acylphosphine oxide-based compound, a titanocene-based compound, an oxime ester-based compound, a benzoin ether-based compound, and a thioxanthone.
[12] The adhesive composition according to any one of [7] to [11], wherein the content of the photopolymerization initiator is 0.01 to 8 parts by mass based on 100 parts by mass of the adhesive composition.
[13] The adhesive composition according to any one of [1] to [12], wherein the adhesive composition further comprises a moisture curing accelerator.
[14] The adhesive composition according to any one of [1] to [13], wherein the moisture-curable resin has a weight average molecular weight of 1000 to 50000.
[15] The adhesive composition according to any one of [1] to [14], wherein the content of the moisture-curable resin is 40 parts by mass or more and 95 parts by mass or less relative to 100 parts by mass of the adhesive composition.
[16] The adhesive composition according to any one of [1] to [15], which has photocurability.
[17] The cured product of the adhesive composition according to any one of [1] to [16 ].
[18] An adhesive for electronic parts, which is formed from the adhesive composition of any one of [1] to [16 ].
[19] An adhesive for a portable electronic device, which is formed of the adhesive composition of any one of [1] to [16 ].
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a moisture-curable adhesive having sufficient impact resistance can be provided even when the metal is an adherend.
Drawings
Fig. 1 is a schematic view showing a method of evaluating adhesion, fig. 1 (a) is a plan view, and fig. 1 (b) is a side view.
Fig. 2 is a schematic side view showing an evaluation method of impact resistance.
Detailed Description
[ Adhesive composition ]
The adhesive composition of the present invention comprises a moisture-curable resin and a silane coupling agent. Hereinafter, the above-described process will be described in detail.
Silane coupling agent
The silane coupling agent has a nitrogen-containing heterocycle. The silane coupling agent has a nitrogen-containing heterocycle, and therefore, even when the adherend of the adhesive composition is a metal, impact resistance of the adhesive composition can be sufficiently exhibited. The principle is not certain, but it is considered that the adhesive composition is not easily peeled off from the adherend because the metal atom of the adherend is coordinately bonded to the nitrogen atom.
The number of nitrogen atoms in one molecule in the silane coupling agent is not particularly limited as long as it is 1 or more, but is preferably 2 or more. The upper limit of the number of nitrogen atoms is preferably 10 or less, more preferably 8 or less. The position of the nitrogen atom in the nitrogen-containing heterocycle is not particularly limited.
From the viewpoint of further improving the impact resistance of the adhesive composition, the silane coupling agent having a nitrogen-containing heterocyclic ring preferably has a nitrogen-containing aromatic heterocyclic ring, more preferably has at least one of a triazole skeleton and a triazine skeleton, and still more preferably has at least one of a benzotriazole skeleton and a triazine skeleton.
The silane coupling agent preferably has a reactive silyl group in addition to the above nitrogen-containing heterocycle. The reactive silyl group preferably has at least one of an alkoxy group and a hydroxyl group bonded to a silicon atom, more preferably has an alkoxy group bonded to a silicon atom.
(Silane coupling agent having triazole skeleton)
The silane coupling agent having a triazole skeleton is preferably, for example, an organosilicon compound having a benzotriazole skeleton and a reactive silyl group, which is represented by the following general formula (1).
In the above general formula (1), R 1～R4 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. An aliphatic or aromatic ring skeleton may be formed by combining R 1 with R 2、R2 with R 3, or R 3 with R 4, respectively. When a ring is formed, the total number of carbon atoms of R 1 and R 2、R2 and R 3, or R 3 and R 4 is 2 to 12.R 5 represents an organic group having 1 to 20 carbon atoms, and R 6 represents an alkyl group having 1 to 10 carbon atoms. R 7 represents an alkyl group having 1 to 10 carbon atoms or a hydrogen atom. a represents an integer of 1 to 3, and n represents an integer of 1 or 2.
In formula (1), a is preferably 2 or 3, more preferably 3. If a is 2 or 3, the adhesiveness to an adherend and impact resistance can be easily improved. When n is 1, R 5 is divalent, and when n is 2, R 5 is trivalent. n is preferably 1.
R 5 is preferably an aliphatic group, and may have a linear structure, a cyclic structure, or a branched structure. R 5 may be a hydrocarbon group, but may have a heteroatom such as a nitrogen atom, an oxygen atom, or a sulfur atom, and in this case, may have an ether bond, an ester bond, an amide bond, a thiol bond, a urethane bond, a urea bond, a hydroxyl group, or the like.
Among the above, R 5 is more preferably a divalent saturated hydrocarbon group, and further preferably an alkylene group. The number of carbon atoms of R 5 is preferably 1 to 15.
Specific examples of the alkylene group include methylene, ethylene, n-propylene, butylene, hexylene, heptylene, octylene, and dodecylene.
R 7 is preferably alkyl. The alkyl group of R 6、R7 has preferably 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms, still more preferably 1 to 2 carbon atoms, and most preferably 1 carbon atom. In the above, R 1～R4 is preferably a hydrogen atom.
Specific examples of the alkyl group in R 6、R7 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, neopentyl, isopentyl, sec-pentyl, hexyl, heptyl, octyl and the like. Specific examples of the alkyl group in R 1～R4 include those having 1 to 6 carbon atoms.
Among the above, the compounds represented by the formula (1) are particularly preferably compounds in which n is 1, R 1～R4 is a hydrogen atom, a is 2 or 3, and R 6 and R 7 are each independently selected from methyl or ethyl.
(Silane coupling agent having triazine skeleton)
The silane coupling agent having a triazine skeleton is preferably, for example, a compound having a triazine skeleton and a reactive silyl group represented by the following general formula (2).
In the above general formula (2), R 8 represents an organic group having 1 to 20 carbon atoms, and R 9 represents an alkyl group having 1 to 10 carbon atoms. R 10 represents an alkyl group having 1 to 10 carbon atoms or a hydrogen atom. R 11 and R 12 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. a represents an integer of 1 to 3, and n represents an integer of 1 or 2.
In the formula (2), a is preferably 2 or 3, more preferably 3. If a is 2 or 3, the adhesion to an adherend is easily improved. When n is 1, R 8 is divalent, and when n is 2, R 8 is trivalent. n is preferably 1.
R 8 is preferably an aliphatic group, and may have a linear structure, a cyclic structure, or a branched structure. R 8 may be a hydrocarbon group, but may have a heteroatom such as a nitrogen atom, an oxygen atom, or a sulfur atom, and in this case, may have an ether bond, an ester bond, an amide bond, a thiol bond, a urethane bond, a urea bond, a hydroxyl group, or the like.
Among the above, R 8 is more preferably a divalent saturated hydrocarbon group, and further preferably an alkylene group. The number of carbon atoms of R 8 is preferably 1 to 15.
Specific examples of the alkylene group include methylene, ethylene, n-propylene, butylene, hexylene, heptylene, octylene, and dodecylene.
R 10 is preferably alkyl. The alkyl group of R 9、R10 has preferably 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms, still more preferably 1 to 2 carbon atoms, and most preferably 1 carbon atom.
In the above, R 11、R12 is preferably a hydrogen atom.
Specific examples of the alkyl group in R 9、R10 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, neopentyl, isopentyl, sec-pentyl, hexyl, heptyl, octyl and the like. Specific examples of the alkyl group in R 11、R12 include the same groups as those shown in R 9、R10.
Among the above, the compounds represented by the formula (2) are particularly preferably compounds in which n is 1, R 11、R12 is a hydrogen atom, a is 2 or 3, and R 9 and R 10 are each independently selected from methyl or ethyl.
As the silane coupling agent, commercially available products can be used, and for example, "X-12-1214A" (manufactured by Xinyue chemical Co., ltd.), "VD-5" (manufactured by four-country chemical Co., ltd.) and the like can be used.
The silane coupling agent may be used alone or in combination of 2 or more.
The content of the silane coupling agent is preferably 0.1 part by mass or more and 5 parts by mass or less, more preferably 0.2 part by mass or more and 3 parts by mass or less, and still more preferably 0.5 part by mass or more and 2.5 parts by mass or less, relative to 100 parts by mass of the adhesive composition. If the content of the silane coupling agent is not less than the above lower limit, excellent impact resistance can be exhibited even when the adhesive composition is adhered to a metal plate. On the other hand, if the content of the silane coupling agent is not more than the above-mentioned upper limit value, the adhesive force of the adhesive composition may be set to a level not less than a certain level.
< Moisture curable resin >
Examples of the moisture-curable resin contained in the adhesive composition of the present invention include isocyanate group-containing resins having an isocyanate group in a molecule, and hydrolyzable silyl group-containing resins having a hydrolyzable silyl group in a molecule. The isocyanate groups in the molecule of the isocyanate group-containing resin react with water present in the air, an adherend, or the like, and cure. The hydrolyzable silyl group in the molecule of the resin containing a hydrolyzable silyl group is cured by reaction with water present in the air, an adherend, or the like. Among the above, the moisture-curable resin is preferably a resin containing an isocyanate group.
The moisture-curable resin may be used alone or in combination of 2 or more.
The isocyanate group-containing resin is not particularly limited, and may be an aromatic isocyanate group or an aliphatic isocyanate group, but among them, an aromatic isocyanate group is preferable.
The aromatic isocyanate group is an isocyanate group directly bonded to an aromatic ring, and the aliphatic isocyanate group is an isocyanate group directly bonded to an aliphatic carbon atom.
The aromatic isocyanate group is an isocyanate group derived from an aromatic isocyanate compound, and the details of the aromatic isocyanate compound are as follows. The aliphatic isocyanate group is an isocyanate group derived from an aliphatic isocyanate compound, and the aliphatic isocyanate compound is described in detail below.
The isocyanate group-containing resin may further have a (meth) acryloyl group. If the isocyanate group-containing resin has a (meth) acryl group, the moisture-curable resin may be cured by irradiation of energy rays. In addition, the adhesive strength and impact resistance can be easily improved.
The isocyanate group-containing resin may have a (meth) acryloyl group in at least a part thereof. Therefore, the isocyanate group-containing resin may be used in combination with an isocyanate group-containing resin having a (meth) acryloyl group and an isocyanate group-containing resin having no (meth) acryloyl group. When the resin is used in combination in this way, the impact resistance and the adhesive strength of the adhesive composition can be easily improved.
In the present specification, "(meth) acryl" means acryl or methacryl, and other similar terms are also used.
The (meth) acryloyl group of the isocyanate group-containing resin is preferably derived from a compound having a (meth) acryloyl group, which will be described later. The moisture-curable resin preferably has a (meth) acryloyl group at a terminal. The (meth) acryl group of the moisture-curable resin is preferably reacted by the photo-curing described later, but the reaction by the photo-curing is not necessarily required. That is, the moisture-curable resins may be allowed to react with each other by photo-curing, or may be allowed to react with a radical polymerizable compound described later, but may be allowed to react without reacting.
In the case of having a (meth) acryloyl group, the resin having an isocyanate group is preferably one having an isocyanate group at one end and one having a (meth) acryloyl group at one end, from the viewpoint of easily improving impact resistance and adhesion of the adhesive composition.
The moisture-curable resin contained in the adhesive composition of the present invention preferably contains at least 1 selected from the group consisting of a moisture-curable resin having a polyether skeleton, a moisture-curable resin having a polycarbonate skeleton, and a moisture-curable resin having a polyester skeleton. When these moisture-curable resins are used, impact resistance and adhesion are easily improved.
These moisture-curable resins may be contained singly or in combination of 2 kinds. Among them, from the viewpoint of improving impact resistance and adhesion of the adhesive composition, the adhesive composition further preferably contains a moisture-curable resin having a polycarbonate skeleton or a moisture-curable resin having a polyester skeleton, and more preferably contains a moisture-curable resin having a polycarbonate skeleton.
(Moisture-curable urethane resin)
The moisture-curable resin is preferably a moisture-curable urethane resin. Therefore, the moisture-curable resin preferably has a urethane bond in addition to an isocyanate group. By using a moisture-curable urethane resin as the moisture-curable resin, impact resistance and the like can be easily improved. In addition, the moisture-curable urethane resin may further have a (meth) acryl group in addition to the isocyanate group and the urethane bond. By using a moisture-curable urethane resin having a (meth) acryloyl group, impact resistance and adhesion can be easily further improved. The moisture-curable urethane resin is preferably used in combination with a moisture-curable urethane resin having a (meth) acryloyl group and a moisture-curable urethane resin having no (meth) acryloyl group.
Hereinafter, the case where the moisture-curable resin is a moisture-curable urethane resin will be described in more detail.
The moisture-curable urethane resin is preferably, for example, a polyol compound or a compound obtained by reacting a polyisocyanate compound.
In the case of having a (meth) acryloyl group, the moisture-curable urethane resin is preferably obtained by reacting a compound having a (meth) acryloyl group in addition to the polyol compound and the polyisocyanate compound. Specifically, the reaction product obtained by reacting a polyol compound with a polyisocyanate compound can be obtained by further reacting the reaction product with a compound having an isocyanate group or a hydroxyl group and a (meth) acryloyl group. Further, the polyol compound and the reaction product obtained by reacting the polyol compound with a compound having an isocyanate group and a (meth) acryloyl group may be obtained by reacting the polyol compound with a polyisocyanate compound. The polyol compound may be obtained by reacting a polyisocyanate compound, a reaction product obtained by reacting a compound having a hydroxyl group and a (meth) acryloyl group, and the like. Further, the moisture-curable urethane resin can be obtained by simultaneously and concurrently reacting a polyol compound, a polyisocyanate compound, and a compound having an isocyanate group or a hydroxyl group and a (meth) acryloyl group.
Further, in the synthesis of the moisture-curable urethane resin having a (meth) acryloyl group, a moisture-curable urethane resin having no (meth) acryloyl group may be synthesized together.
The reaction of the polyol compound with the polyisocyanate compound or the reaction of the polyol compound with the polyisocyanate compound and the compound having a (meth) acryloyl group is usually carried out in such a manner that the molar ratio of hydroxyl group (OH) to isocyanate group (NCO) in these compounds is in the range of [ NCO ]/[ OH ] =2.0 to 2.5.
In the present invention, the polyether polyol is used as the polyol compound that is a raw material of the moisture-curable urethane resin, and the polyether skeleton is introduced into the moisture-curable urethane resin to prepare the moisture-curable urethane resin having a polyether skeleton. More specifically, the urethane resin having a polyether skeleton can be obtained by reacting a polyether polyol having 2or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2or more isocyanate groups in 1 molecule.
Further, a polyester polyol is used as the polyol compound that is a raw material of the moisture-curable urethane resin, so that the polyester skeleton is introduced into the moisture-curable urethane resin, and a moisture-curable urethane resin having a polyester skeleton may be produced.
In the case of obtaining a moisture-curable urethane resin having a polycarbonate skeleton, the polycarbonate skeleton may be introduced into the moisture-curable urethane resin by using a polycarbonate polyol as a polyol compound that is a raw material of the moisture-curable urethane resin.
Examples of the polyether polyol used for obtaining the moisture-curable urethane resin having a polyether skeleton include a ring-opening polymer of ethylene glycol, propylene glycol, tetrahydrofuran, a ring-opening polymer of 3-methyltetrahydrofuran, a random copolymer or a block copolymer of these or a derivative thereof, a bisphenol-type polyoxyalkylene modified body, and the like. Among them, propylene glycol or a ring-opening polymer of 3-methyltetrahydrofuran is preferable from the viewpoint of easiness of improving the coatability of the photo moisture-curable resin composition.
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 bisphenol-type polyoxyalkylene modified product is preferably one in which 1 or 2 or more kinds of alkylene oxides are added 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 general formula (3). By using the polyol compound having a structure represented by the following general formula (3), a photo-moisture-curable resin composition excellent in adhesion and a cured product excellent in flexibility and elongation can be obtained, and compatibility with a radical-polymerizable compound is excellent.
Among them, polyether polyols formed from ring-opening polymerization compounds of propylene glycol, tetrahydrofuran (THF) compounds, or ring-opening polymerization compounds of tetrahydrofuran compounds having a substituent such as methyl group are preferably used, and propylene glycol is more preferred.
In formula (3), R 13 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 13 is directly bonded to oxygen.
In the above, the total of n and l is more preferably 1 or more, and still more preferably 1 to 3. R 13 is more preferably a hydrogen atom or a methyl group, and particularly preferably a methyl group.
As the polycarbonate polyol used for obtaining the moisture-curable urethane resin having a polycarbonate skeleton, a polycarbonate diol is preferable. Specific examples of the polycarbonate diol include compounds represented by the following general formula (4).
In the general formula (4), R is a divalent hydrocarbon group having 4 to 16 carbon atoms, and n is an integer of 2 to 500.
In the above general formula (4), R is preferably an aliphatic saturated hydrocarbon group. R is an aliphatic saturated hydrocarbon group, and thus heat resistance and flexibility are likely to be improved. Further, yellowing and the like are also 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, and preferably has a chain structure. 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.
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. In addition, it is preferable to include 2 or more kinds of R in one molecule, and it is more preferable to include 2 or 3 kinds of R in one molecule.
The chain aliphatic saturated hydrocarbon group having 6 or more carbon atoms preferably has 6 or more and 12 or less carbon atoms, more preferably has 6 or more and 10 or less carbon atoms, still more preferably has 6 or more and 8 or less 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. The plurality of R's in a molecule may be the same or different from each other. Further, R preferably contains a branched aliphatic saturated hydrocarbon group from the viewpoint of setting the elastic modulus to a predetermined value or more, and R preferably contains a linear aliphatic saturated hydrocarbon group from the viewpoint of weather resistance. R in the polycarbonate polyol may be a combination of branched and linear R.
The polycarbonate polyol may be used alone or in combination of 1 or more than 2.
Examples of the polyester polyol used for obtaining the moisture-curable urethane resin having a polyester skeleton 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. The polyester polyol is preferably a polyester diol.
Examples of the polycarboxylic acid as a raw material of the polyester polyol include divalent aromatic carboxylic acids such as terephthalic acid, isophthalic acid, 1, 5-naphthalenedicarboxylic acid, 2, 6-naphthalenedicarboxylic acid, etc., divalent aliphatic carboxylic acids such as succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decamethylenedicarboxylic acid, dodecamethylenedicarboxylic acid, etc., trivalent or more aromatic carboxylic acids such as trimellitic acid, pyromellitic acid, naphthalene tricarboxylic acid, etc., trivalent or more aliphatic carboxylic acids such as cyclohexane tricarboxylic acid, hexane tricarboxylic acid, etc. These polycarboxylic acids may be used singly or in combination of 1 or 2 or more.
Examples of the polyhydric alcohol 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.
In the moisture-curable urethane resin, 1 kind may be used alone or 2 or more kinds may be used in combination as the polyol compound. In the case where 2 or more kinds of the polyol compounds are used, 2 or more kinds selected from the group consisting of polyether skeleton, polycarbonate skeleton, and polyester skeleton may be introduced into the moisture-curable urethane resin. That is, the moisture-curable urethane resin may be produced to have 2 or more moisture-curable urethane resins selected from the group consisting of polyether skeleton, polycarbonate skeleton, and polyester skeleton in one molecule.
The polyisocyanate compound that is a raw material of the moisture-curable urethane resin has 2 or more isocyanate groups in 1 molecule, but preferably has 2 isocyanate groups. Examples of the polyisocyanate compound include aromatic polyisocyanate compounds and aliphatic polyisocyanate compounds.
Examples of the aromatic polyisocyanate compound include diphenylmethane diisocyanate, a liquid modified diphenylmethane diisocyanate, toluene diisocyanate, naphthalene-1, 5-diisocyanate, and the like. The aromatic polyisocyanate compound may be a compound obtained by polymerizing them, or may be a polymeric MDI. The aromatic polyisocyanate compound is preferably diphenylmethane diisocyanate.
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. The aliphatic polyisocyanate compound may be a compound obtained by polymerizing them.
The polyisocyanate compound may be used alone or in combination of 1 or more than 2.
In the present invention, in the synthesis of the moisture-curable urethane resin, the moisture-curable resin contains an aromatic isocyanate group if an aromatic polyisocyanate compound is used, and contains an aliphatic isocyanate group if an aliphatic polyisocyanate compound is used. Therefore, as the polyisocyanate compound, an aromatic polyisocyanate compound is preferably used.
The compound having a (meth) acryloyl group used as a raw material in the synthesis of the moisture-curable urethane resin having a (meth) acryloyl group is preferably one having an isocyanate group or a hydroxyl group as described above, but is preferably one having an isocyanate group and a (meth) acryloyl group from the viewpoint of enabling the (meth) acryloyl group to be easily introduced into the moisture-curable urethane resin. Examples of the compound having an isocyanate group and a (meth) acryloyl group include compounds represented by the following general formula (5).
In the above general formula (5), R 14 represents hydrogen or methyl, and R 15 represents a divalent saturated hydrocarbon group having 1 to 10 carbon atoms which may have an ether bond.
The compound having an isocyanate group and a (meth) acryloyl group is preferably 2- (meth) acryloyloxyethyl isocyanate, 2- (meth) acryloyloxyethoxyethyl isocyanate, or the like.
Examples of the compound having a hydroxyl group and a (meth) acryloyl group which is a raw material of the moisture-curable urethane resin include hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
Further, as the compound having a (meth) acryloyl group which is a raw material of the moisture-curable urethane resin, a compound obtained by reacting these compounds having a hydroxyl group and a (meth) acryloyl group with various diisocyanate compounds in such a ratio that the isocyanate group/hydroxyl group (molar ratio) becomes 2, or the like, may be used.
In the present invention, it is preferable to use the isocyanate group-containing resin having a (meth) acryloyl group in combination with the isocyanate group-containing resin having no (meth) acryloyl group as described above. In this case, the content ratio (mass ratio) of the isocyanate group-containing resin having a (meth) acryloyl group to the isocyanate group-containing resin having no (meth) acryloyl group is preferably 1/20 or more and 1/1 or less, more preferably 1/15 or more and 1/2 or less, and still more preferably 1/12 or more and 1/3 or less. When the content ratio is within the above range, the impact resistance and the adhesive strength of the adhesive composition can be easily improved.
The weight average molecular weight of the moisture-curable resin is not particularly limited, but is preferably 1000 to 50000, more preferably 2000 to 30000, still more preferably 3000 to 20000. When the weight average molecular weight is not less than the above lower limit, the crosslinking density does not become too high at the time of curing, and the flexibility after curing tends to be high. Further, for example, in a semi-cured state after photo-curing and before moisture curing, it has a hardness of a certain or more, and it is easy to secure excellent shape retention. Further, when the weight average molecular weight is equal to or less than the upper limit, the adhesive composition tends to have moderate fluidity even at ordinary temperature (for example, 25 ℃) before curing, and the coating property is improved.
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. As a column for measuring the weight average molecular weight obtained by conversion of polystyrene by GPC, shodex LF-804 (manufactured by Showa electric Co., ltd.) is exemplified. Further, as a solvent used in GPC, tetrahydrofuran is exemplified.
The content of the moisture-curable resin in the adhesive composition is, for example, 40 parts by mass or more and 95 parts by mass or less, preferably 45 parts by mass or more and 90 parts by mass or less, and more preferably 50 parts by mass or more and 75 parts by mass or less, based on 100 parts by mass of the adhesive composition. When the content of the moisture-curable resin is not less than the above lower limit, an adhesive composition excellent in adhesive force and impact resistance can be obtained. On the other hand, if the content of the moisture-curable resin is not more than the above-mentioned upper limit value, an adhesive composition excellent in shape retention can be obtained.
(Radical polymerizable Compound)
The photo moisture curable resin composition of the present invention preferably contains a radical polymerizable compound. The photo-moisture curable resin composition can impart good shape retention to the adhesive composition by containing the radical polymerizable compound, and can produce an adhesive having excellent practicality.
The radical polymerizable compound is not particularly limited, and various aliphatic (meth) acrylic compounds can be used, and aliphatic urethane (meth) acrylates and the like are preferably used. The aliphatic urethane (meth) acrylate has no residual isocyanate group. The other radical polymerizable compound may be monofunctional or may be multifunctional such as 2-functional.
As the aliphatic 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 aliphatic urethane (meth) acrylate include aliphatic monoisocyanates such as alkane monoisocyanates (the number of carbon atoms of the alkane is preferably about 3 to 12) such as butane isocyanate, hexane isocyanate, octane isocyanate and decane isocyanate, and cyclic aliphatic monoisocyanates such as cyclopentane isocyanate, cyclohexane isocyanate and isophorone monoisocyanate.
The monofunctional aliphatic urethane (meth) acrylate is more specifically 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 suitable include 1, 2-ethylene glycol 1-acrylate 2- (N-alkyl urethane) such as 1, 2-ethylene glycol 1-acrylate 2- (N-butyl urethane).
As the radical polymerizable compound, urethane (meth) acrylate may be used, and for example, a (meth) acrylate compound other than the above may be used. The (meth) acrylate compound may be monofunctional or polyfunctional, but is preferably monofunctional.
Examples of the monofunctional substance among the (meth) acrylate compounds include (meth) acrylic acid alkyl esters 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, etc. (meth) acrylic acid alkyl esters such as cyclohexyl (meth) acrylate, 4-t-butylcyclohexyl (meth) acrylate, 3, 5-trimethylcyclohexyl (meth) acrylate, (meth) acrylic acid isobornyl (meth) acrylate, (meth) acrylic acid dicyclopentenyl (meth) acrylate, etc. (meth) acrylate having an alicyclic structure, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, (2-hydroxybutyl (meth) acrylate, (meth) 2-hydroxybutyl (meth) acrylate, 4-hydroxyalkyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, etc. (meth) acrylate, 2-hydroxyethyl (meth) acrylate, etc, alkoxyalkyl (meth) acrylates such as 2-butoxyethyl (meth) acrylate, alkoxyethylene glycol (meth) acrylate such as methoxyethylene glycol (meth) acrylate and ethoxyethylene glycol (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, ethoxytriethylene glycol (meth) acrylate, and polyoxyethylene (meth) acrylates such as ethoxypolyethylene glycol (meth) acrylate.
Further, examples of the monofunctional (meth) acrylate compound include (meth) acrylate having a heterocyclic structure such as tetrahydrofurfuryl (meth) acrylate, alkoxylated tetrahydrofurfuryl (meth) acrylate, cyclic trimethylolpropane formal (meth) acrylate, 3-ethyl-3-oxetanylmethyl (meth) acrylate, 2-trifluoroethyl (meth) acrylate, 2, 3-tetrafluoropropyl (meth) acrylate, 1h,5 h-octafluoropentyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, glycidyl (meth) acrylate, and 2- (meth) acryloyloxyethyl phosphate.
Examples of the 2-functional substance among the (meth) acrylate compounds 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, dimethylol dicyclopentadienyl di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide modified isocyanuric 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, polycaprolactone di (meth) acrylate, and polybutadiene (meth) acrylate.
Examples of the 3-functional or higher compound among the (meth) acrylate compounds include trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, ethylene oxide-added isocyanurate tri (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide-added 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 other radical polymerizable compound, other radical polymerizable compounds other than the above may be suitably used. Examples of the other radically polymerizable compound include (meth) acrylamide compounds such as N, N-dimethyl (meth) acrylamide, N- (meth) acryloylmorpholine, N-hydroxyethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-dimethylaminopropyl (meth) acrylamide, and vinyl compounds such as N-vinyl-2-pyrrolidone and N-vinyl-epsilon-caprolactam. In addition, epoxy (meth) acrylate and the like may also be used.
The content of the radical polymerizable compound is preferably 4 parts by mass or more, more preferably 9 parts by mass or more, and still more preferably 24 parts by mass or more, based on 100 parts by mass of the adhesive composition. When the lower limit value is not less than the above, the adhesive composition is easily provided with good shape retention. In addition, the adhesive composition is easy to be coated well.
The content of the radical polymerizable compound is preferably 59 parts by mass or less, more preferably 50 parts by mass or less, and further preferably 45 parts by mass or less, based on 100 parts by mass of the adhesive composition. By setting the content of the radical polymerizable compound to not more than the upper limit value, the moisture-curable resin in the adhesive composition can be set to a certain amount or more, and an adhesive composition excellent in adhesive force and impact resistance can be easily obtained.
The content ratio (mass ratio) of the radical polymerizable compound to the moisture-curable resin in the adhesive composition is preferably 1/10 or more and 15/10 or less, more preferably 2/10 or more and 10/10 or less, and still more preferably 4/10 or more and 9/10 or less. When the content ratio of the radical polymerizable compound to the moisture-curable resin is not less than the above lower limit, the adhesive composition is easily provided with good shape retention. In addition, the adhesive composition is easy to be coated well. Further, when the content ratio of the radical polymerizable compound to the moisture-curable resin is not more than the above-mentioned upper limit value, it is easy to obtain an adhesive composition excellent in adhesive force and impact resistance.
(Photopolymerization initiator)
The adhesive composition of the present invention may further contain a photopolymerization initiator. The adhesive composition can be appropriately provided with photocurability and the like by containing the photopolymerization initiator. When the adhesive composition contains a radical polymerizable compound, a photopolymerization initiator is preferably used.
Examples of the photopolymerization initiator include benzophenone-based compounds, acetophenone-based compounds, acylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin ether-based compounds, and thioxanthones.
Examples of commercially available photopolymerization initiators include ,IRGACURE184、IRGACURE369、IRGACURE379、IRGACURE651、IRGACURE784、IRGACURE819、IRGACURE907、IRGACURE2959、IRGACURE OXE01、ルシリンTPO (which are all available from BASF), benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (which are all available from Tokyo Chemical Industry Corporation), and the like.
The content of the photopolymerization initiator in the adhesive composition is preferably 0.01 parts by mass or more and 8 parts by mass or less, more preferably 0.1 parts by mass or more and 6 parts by mass or less, and still more preferably 0.4 parts by mass or more and 4 parts by mass or less, relative to 100 parts by mass of the adhesive composition. The content of the photopolymerization initiator falls within these ranges, and the resulting adhesive composition is excellent in shape retention. Further, in the above range, the photoradical polymerizable compound is properly cured, and thus the adhesion is easily improved.
(Moisture curing acceleration catalyst)
The adhesive composition of the present invention may contain a moisture curing accelerator for accelerating the moisture curing reaction of the moisture curable resin. By using the moisture curing accelerator, the adhesive composition is more excellent in moisture curability and the adhesive strength can be 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 in the adhesive composition is preferably 0.1 part by mass or more and 10 parts by mass or less, more preferably 0.2 part by mass or more and 8 parts by mass or less, and still more preferably 0.3 part by mass or more and 5 parts by mass or less, relative to 100 parts by mass of the adhesive composition.
(Filler)
The adhesive composition of the present invention may contain a filler. By containing the filler, the adhesive composition of the present invention has suitable thixotropic properties and is easy to maintain a good shape after application. As the filler, a particulate material may be used.
The filler is preferably an inorganic filler, and examples thereof include silica, talc, titanium oxide, zinc oxide, and calcium carbonate. Among them, silica is preferable because of excellent ultraviolet transmittance of the adhesive composition. The filler may be subjected to hydrophobic surface treatments such as silylation, alkylation and epoxidation.
The filler may be used alone or in combination of 1 or more than 2.
The content of the filler is preferably 0.5 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 25 parts by mass or less, and still more preferably 2 parts by mass or more and 15 parts by mass or less, relative to 100 parts by mass of the adhesive composition.
The adhesive composition of the present invention may contain, in addition to the above-described components, other additives such as a titanate-based coupling agent, a zirconate-based coupling agent, a coupling agent such as a silane coupling agent having no nitrogen-containing heterocycle, wax particles, an ionic liquid, a colorant, expanded particles, a reactive diluent, an antioxidant, a radical scavenger, and the like.
The adhesive composition may be diluted with a solvent as needed. When the adhesive composition is diluted with a solvent, the amounts (parts by mass, mass%) of the adhesive composition are based on the solid content, that is, refer to parts by mass, mass% excluding the solvent.
Examples of the method for producing the adhesive composition of the present invention include a method in which a moisture-curable resin, a silane coupling agent having a nitrogen-containing heterocycle, and other additives such as a radical-polymerizable compound, a photopolymerization initiator, a moisture-curing accelerator, and a filler, which are mixed as needed, are mixed using a mixer. Examples of the mixer include a homomixer, a universal mixer, a planetary mixer (planetary stirring device), a kneader, and three rolls.
< Method of use >)
The adhesive composition of the present invention is preferably used as a cured product by curing. The adhesive composition of the present invention has at least moisture curability. Accordingly, the adhesive composition is preferably an adhesive composition (cured product) obtained by disposing an adhesive composition or a semi-cured adhesive composition between a pair of adherends and bonding the pair of adherends by an adhesive composition (cured product) cured at least by moisture.
The adhesive composition of the present invention is preferably photocurable, preferably by having a radical polymerizable compound. That is, the adhesive composition is preferably used as a photo moisture curable type. Therefore, the adhesive composition of the present invention is preferably used by being light-cured by light irradiation to form, for example, a B-stage state (semi-cured state), and then being further cured by moisture to be fully cured.
Here, when the adhesive composition is disposed between the adherends and the adherends are bonded to each other, it is preferable to apply the adhesive composition to one of the adherends, then to apply the adhesive composition to the other of the adherends by irradiation with light to cure the adhesive composition in a B-stage state, and to temporarily bond the adherends to each other with a proper bonding force. Then, the adhesive composition in the B-stage state is cured by moisture to cure the moisture-curable resin, and the superimposed adherends are bonded with sufficient adhesive force via the adhesive composition.
The adhesive composition is preferably applied to an adherend, for example, by a dispenser, but is not particularly limited. The light to be irradiated during the photo-curing is not particularly limited as long as it is light to cure one or both of the moisture-curable resin and the radical-polymerizable compound, but is preferably ultraviolet light. In addition, when the adhesive composition is fully cured by moisture, the adhesive composition may be left in the atmosphere for a predetermined period of time.
The adhesive composition of the present invention is used, for example, as an adhesive for electronic components. The adhesive composition of the present invention is preferably used as an adhesive for electronic devices, particularly for portable electronic devices. Further, an electronic component or a portable electronic device using the adhesive composition of the present invention preferably has a cured body of the adhesive composition.
The adherend using the adhesive composition is not particularly limited, but is preferably a component constituting a portable electronic device, and the component is preferably an electronic component. The material of the adherend may be any of metal, glass, plastic, and the like, but it is preferable that at least one of the adherends is metal. 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, and a case shape.
The portable electronic device is not particularly limited, and examples thereof include a mobile phone such as a smart phone, a digital camera, a wearable terminal, a portable game device, a tablet computer, a notebook computer, and a sports camera, and among them, a smart phone and a wearable terminal are preferable. The adhesive composition of the present invention is particularly suitable for portable electronic devices because of its excellent impact resistance.
Since an electronic component generally has a substrate, it is preferable that an electronic component using the adhesive composition of the present invention has a cured product of the adhesive composition and a substrate. Various electronic circuits and the like are generally provided on the substrate. In the same manner, electronic devices such as portable electronic devices using the adhesive composition of the present invention preferably also have a cured product of the adhesive composition of the present invention and a substrate.
For example, the substrates may be an adherend, and the substrates may be bonded to each other via the adhesive composition of the present invention, or the substrates may be bonded to other members (for example, a case) of an electronic device via the adhesive composition of the present invention.
For example, the adhesive composition of the present invention can be used in an electronic device or the like, for example, to obtain an assembled component by bonding a substrate to a substrate. 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 and at least a part of the 2 nd substrate are joined via the cured body.
Examples
The present invention will be described in further detail with reference to examples, but the present invention is not limited to these examples.
In this example, the adhesive composition was evaluated as follows.
(PUSH adhesive force)
As shown in fig. 1 (a), a 1 st substrate 11 having a circular hole 11A of 90mm×50mm and 5mm in thickness and 12mm in diameter in the center and a 2 nd substrate 12 of 50mm×50mm and 5mm in thickness were prepared. The 1 st substrate 11 is made of Aluminum (AL), and the 2 nd substrate 12 is made of Polycarbonate (PC).
The adhesive composition 10 was applied in a rectangular frame shape having a width of 1 mm.+ -. 0.2mm, a height of 0.25 mm.+ -. 0.05mm and a height of 20 mm.+ -. 20mm using a dispenser so as to surround the hole 11A of the 1 st substrate 11. The adhesive composition 10 was photo-cured by irradiating ultraviolet rays at 1000mJ/cm 2 with a UV-LED (wavelength 365 nm) within 1 minute after the completion of the coating. Then, the 1 st and 2 nd substrates 11 and 12 were pressure-bonded via the adhesive composition 10 by superposing the 2 nd substrate 12 on the 1 st substrate 11 and further allowing a weight of 2kg to stand on the 2 nd substrate 12 for 10 seconds so that the central positions of the 1 st and 2 nd substrates 11 and 12 were aligned with each other via a spacer (not shown) having a height of 0.2mm and the adhesive composition 10. Then, 2kg of the weight was removed, and the mixture was left at 25℃and 50% RH for 24 hours, whereby the adhesive composition 10 was moisture-cured, and a measurement sample 13 was obtained. After moisture curing, the spacer is removed from the measurement sample 13.
In the obtained measurement sample 13, the 1 st substrate 11 was placed on the upper side and the 2 nd substrate 12 was placed on the lower side, and a rod-shaped member 14 having a circular cross section and a diameter of 10mm was inserted into the hole 11A in a state where the 1 st substrate 11 was supported by a stainless steel jig. Further, as shown in fig. 1 (b), the 2 nd substrate 12 was pushed vertically downward at a speed of 10 mm/min by the bar-shaped member 14, and the stress at the time of peeling the 2 nd substrate 12 from the 1 st substrate 11 was measured to be a PUSH adhesion.
(Impact resistance)
As shown in fig. 2, a measurement sample 13 was prepared in the same manner as described above, and the 1 st substrate 11 was placed on the upper side and the 2 nd substrate 12 was placed on the lower side, and then the 1 st substrate 11 was supported by a stainless steel jig.
Further, a jig 16 (material: stainless steel) having a flat plate portion 16B (20 mm. Times.20 mm, 5mm in thickness) and a rod portion 16A (10 mm in diameter, cylindrical) connected to the center of the flat plate portion 16B was prepared, and the rod portion 16A of the jig 16 was inserted into the hole 11A of the 1 st substrate 11 to stand on the center of the 2 nd substrate 12 as shown in FIG. 2.
In this state, a dupont type dropping impact tester was used to repeatedly drop a 300g stainless steel weight 15 vertically downward from a position of 200mm relative to the height of the flat plate portion 16B, and the number of dropping times of the weight until the 2 nd substrate 12 was peeled off by the impact of the weight 15 was set as the number of durability times.
(Shape retentivity)
The 1 st and 2 nd substrates were prepared in the same manner as in the case of preparing the measurement sample, and the 1 st substrate was coated with the adhesive composition and cured by light.
Then, the 1 st substrate and the 2 nd substrate were stacked on the 1 st substrate so that the center positions of the 1 st and 2 nd substrates were aligned with each other via the adhesive composition without using a spacer, and a weight of 100g was further left to stand on the 2 nd substrate for 10 seconds, and the 1 st and 2 nd substrates were pressure-bonded via the adhesive composition, whereby the weight was removed. The thickness of the adhesive composition after the weight was removed was measured. The thickness of the adhesive composition was evaluated as "B" when it became less than 0.15mm, and as "A" when it became 0.15mm or more.
The moisture curable resins used in the examples and comparative examples were prepared according to the following synthesis examples.
Moisture-curable resin (A)
Synthesis example 1
100 Parts by mass of polytetramethylene ether glycol (trade name "PTMG-2000", manufactured by Mitsubishi chemical corporation) and 0.01 parts by mass of dibutyltin dilaurate as a polyol compound were charged into a 500-mL-capacity separable flask, and stirred under vacuum (20 mmHg or less) at 100℃for 30 minutes to mix. Then, 26.5 parts by mass of diphenylmethane diisocyanate (trade name "Pure MDI" manufactured by soh corporation) as a polyisocyanate compound was added thereto at normal pressure, and the mixture was stirred at 80℃for 3 hours to react the resultant mixture, thereby obtaining a moisture-curable urethane resin (ether skeleton aromatic terminal urethane) having a polyether skeleton and aromatic isocyanate groups at both ends. The weight average molecular weight of the obtained moisture-curable urethane resin was 2700.
Moisture-curable resin (B)
Synthesis example 2
100 Parts by mass of a polycarbonate diol (a compound represented by the formula (3), 90 mol% of R being 3-methylpentylene, 10 mol% being 1, 6-hexylene, manufactured by Kyoto Larre Louis 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 placed under vacuum (20 mmHg or less), and stirred at 100℃for 30 minutes to mix. Then, 50 parts by mass of diphenylmethane diisocyanate (trade name "dye MT" manufactured by Tongso Co., ltd.) as a polyisocyanate compound was added thereto at normal pressure, and the mixture was stirred at 80℃for 3 hours to react the mixture, thereby obtaining a moisture-curable urethane resin (2-1) having a Polycarbonate (PC) skeleton and isocyanate groups at both ends. The weight average molecular weight of the obtained moisture-curable urethane resin (2-1) was 6000.
Moisture-curable resin (C)
Synthesis example 3
100 Parts by mass of a polycarbonate diol (a compound represented by the formula (3), 90 mol% of R being 3-methylpentylene, 10 mol% being 1, 6-hexylene, manufactured by Kyoto Larre Louis 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 placed under vacuum (20 mmHg or less), and stirred at 80℃for 60 minutes to mix. Then, 30 parts by mass of 2-methacryloyloxyethyl isocyanate (trade name: a cord MOI, manufactured by Showa electric Co., ltd.) was added to the obtained reaction product at normal pressure, and the mixture was stirred at 100℃for 3 hours to react the reaction product, thereby obtaining a reaction product having a Polycarbonate (PC) skeleton and a methacryloyl group at one end.
50 Parts by mass of diphenylmethane diisocyanate (trade name "m/t" from the east koto company) as a polyisocyanate compound was added to the obtained reaction product, and the mixture was stirred at 80 ℃ for 3 hours to react the mixture, thereby obtaining a moisture-curable urethane resin (3-1) having a Polycarbonate (PC) skeleton. The moisture-curable urethane resin (A1) having a methacryloyl group at one end and an isocyanate group at one end was contained in the moisture-curable urethane resin (3-1) in an amount of 80% by mass. The moisture-curable urethane resin (3-1) also contains a moisture-curable urethane resin having isocyanate groups at both ends. The weight average molecular weight of the obtained moisture-curable urethane resin (3-1) was 5000.
The components other than the moisture-curable urethane resin used in each of the examples and comparative examples are as follows.
(Radical polymerizable Compound)
Urethane acrylate: the product of the division, trade name "EBECRYL8411", is made by the division cover "
Lauryl acrylate: trade name "Larapy mountain" manufactured by Kagaku chemical Co., ltd., monofunctional
(Silane coupling agent)
Nitrogen-containing silane coupling agent 1: in the above general formula (1), R 1～R4 is a hydrogen atom, a=3, n=1, R 7 is a methyl group, and the silane coupling agent having a triazole skeleton is manufactured by Xinyue chemical industry Co., ltd., trade name "X-12-1214A"
Nitrogen-containing silane coupling agent 2: in the above general formula (2), R 11 and R 12 are hydrogen atoms, a=3, n=1, and R 10 is an ethyl group, and the silane coupling agent has a triazine skeleton, and is available under the trade name "VD-5" from the chemical industry of four countries "
Isocyanate group-containing silane coupling agent: trade name "KBE-9007" manufactured by Xinyue chemical Co., ltd "
(Filler)
Trimethylsilylated silica, trade name "R812" manufactured by Japanese A/d, primary particle size 7nm
(Photopolymerization initiator)
2-Benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, manufactured by BASF corporation under the trade name "IRGACURE 369"
(Other additives)
Radical scavenger
Antioxidant(s)
Moisture curing catalyst
Examples 1 to 9 and comparative examples 1 to 8
According to the mixing ratios shown in tables 1 and 2, the materials were mixed with a planetary stirring device (manufactured by screw company, "awatori" is stirred at a temperature of 50 ℃, the adhesive compositions of examples 1to 9 and comparative examples 1to 8 were obtained by uniformly mixing the ceramic three rolls at a temperature of 50 ℃.
TABLE 1
TABLE 1
TABLE 2
TABLE 2
As shown in tables 1 and 2, the adhesive compositions of the examples contain the silane coupling agent containing a nitrogen atom, and thus, compared with the comparative examples containing the silane coupling agent containing no nitrogen atom or the comparative examples containing no silane coupling agent, the adhesive compositions of the examples can be excellent in both adhesion and impact resistance even when the adherend is a metal substrate.
Claims (9)
1. An adhesive composition comprising a moisture-curable resin and a silane coupling agent having a nitrogen-containing heterocycle.
2. The adhesive composition according to claim 1, wherein the silane coupling agent has at least one of a triazole skeleton and a triazine skeleton.
3. The adhesive composition according to claim 1 or 2, wherein the content of the silane coupling agent is 0.1 parts by mass or more and 5 parts by mass or less relative to 100 parts by mass of the adhesive composition.
4. The adhesive composition according to any one of claims 1 to 3, wherein the moisture-curable resin comprises at least 1 selected from the group consisting of a moisture-curable resin having a polyether skeleton, a moisture-curable resin having a polycarbonate skeleton, and a moisture-curable resin having a polyester skeleton.
5. The adhesive composition according to any one of claims 1 to 4, wherein the moisture-curable resin comprises an isocyanate group-containing resin having an isocyanate group in a molecule.
6. The adhesive composition according to claim 5, wherein the moisture-curable resin comprises an isocyanate group-containing resin having an isocyanate group and a (meth) acryloyl group in a molecule.
7. The adhesive composition according to any one of claims 1 to 6, further comprising a radical polymerizable compound, and a photopolymerization initiator.
8. An adhesive for electronic parts, which is formed from the adhesive composition according to any one of claims 1 to 7.
9. An adhesive for portable electronic devices, which is formed from the adhesive composition according to any one of claims 1 to 7.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2021201979 | 2021-12-13 | ||
| JP2021-201979 | 2021-12-13 | ||
| PCT/JP2022/045596 WO2023112873A1 (en) | 2021-12-13 | 2022-12-12 | Adhesive composition, adhesive for electronic components, and adhesive for portable electronic devices |
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| JP (1) | JPWO2023112873A1 (en) |
| KR (1) | KR20240119073A (en) |
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| JP2002363189A (en) * | 2001-06-01 | 2002-12-18 | Yokohama Rubber Co Ltd:The | Silane coupling agent and polymer composition containing the same |
| JP4734605B2 (en) * | 2003-10-10 | 2011-07-27 | Ｊｘ日鉱日石金属株式会社 | Resin composition |
| JP4937595B2 (en) * | 2006-02-07 | 2012-05-23 | オート化学工業株式会社 | One-component moisture-curable composition, sealing material composition, and adhesive composition |
| CN103502372B (en) * | 2011-09-05 | 2014-08-27 | 积水化学工业株式会社 | Adhesive for bonding front plate for display devices, adhesive set for bonding front plate for display devices, method for manufacturing display device, and display device |
| JP2015182969A (en) * | 2014-03-21 | 2015-10-22 | 四国化成工業株式会社 | Triazole silane compound, method for synthesizing the same and use thereof |
| KR101771389B1 (en) | 2016-02-12 | 2017-08-24 | 성풍솔레드 주식회사 | rotary signal lamp |
| JP6609207B2 (en) * | 2016-03-18 | 2019-11-20 | 四国化成工業株式会社 | Triazole silane compound, method for synthesizing the compound and use thereof |
| JPWO2021157624A1 (en) * | 2020-02-05 | 2021-08-12 | ||
| CN119039524A (en) * | 2020-05-15 | 2024-11-29 | 积水化学工业株式会社 | Photo-moisture curable resin composition, adhesive for electronic component, cured body, and electronic component |
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2022
- 2022-12-12 WO PCT/JP2022/045596 patent/WO2023112873A1/en active Application Filing
- 2022-12-12 TW TW111147633A patent/TW202336202A/en unknown
- 2022-12-12 JP JP2023501591A patent/JPWO2023112873A1/ja active Pending
- 2022-12-12 KR KR1020247019317A patent/KR20240119073A/en active Pending
- 2022-12-12 CN CN202280081800.3A patent/CN118369393A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR20240119073A (en) | 2024-08-06 |
| JPWO2023112873A1 (en) | 2023-06-22 |
| WO2023112873A1 (en) | 2023-06-22 |
| TW202336202A (en) | 2023-09-16 |
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