JP2009114352A - Adhesive resin composition and binding material using the same - Google Patents
Adhesive resin composition and binding material using the same Download PDFInfo
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- JP2009114352A JP2009114352A JP2007289601A JP2007289601A JP2009114352A JP 2009114352 A JP2009114352 A JP 2009114352A JP 2007289601 A JP2007289601 A JP 2007289601A JP 2007289601 A JP2007289601 A JP 2007289601A JP 2009114352 A JP2009114352 A JP 2009114352A
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- Prior art keywords
- meth
- resin composition
- adhesive resin
- urethane
- acrylate
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 239000004840 adhesive resin Substances 0.000 title claims abstract description 38
- 229920006223 adhesive resin Polymers 0.000 title claims abstract description 38
- 239000000463 material Substances 0.000 title claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 50
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 26
- 229920005989 resin Polymers 0.000 claims abstract description 20
- 239000011347 resin Substances 0.000 claims abstract description 20
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 30
- 239000000853 adhesive Substances 0.000 claims description 18
- 230000001070 adhesive effect Effects 0.000 claims description 18
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 abstract description 12
- 239000002184 metal Substances 0.000 abstract description 12
- 229910044991 metal oxide Inorganic materials 0.000 abstract description 11
- 150000004706 metal oxides Chemical class 0.000 abstract description 11
- 229910019142 PO4 Inorganic materials 0.000 abstract description 8
- 239000010452 phosphate Substances 0.000 abstract description 8
- 150000002739 metals Chemical class 0.000 abstract description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract description 7
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- -1 IZO or ITO Chemical class 0.000 description 23
- 229920000877 Melamine resin Polymers 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 239000004640 Melamine resin Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000010931 gold Substances 0.000 description 7
- 150000007974 melamines Chemical class 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 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 4
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 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
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- OZDCBKYPNBVRSA-UHFFFAOYSA-N (4,4-dimethoxycyclohexa-1,5-dien-1-yl)-phenylmethanone Chemical compound C1=CC(OC)(OC)CC=C1C(=O)C1=CC=CC=C1 OZDCBKYPNBVRSA-UHFFFAOYSA-N 0.000 description 1
- KFJJYOKMAAQFHC-UHFFFAOYSA-N (4-methoxy-5,5-dimethylcyclohexa-1,3-dien-1-yl)-phenylmethanone Chemical compound C1C(C)(C)C(OC)=CC=C1C(=O)C1=CC=CC=C1 KFJJYOKMAAQFHC-UHFFFAOYSA-N 0.000 description 1
- BWZAUXRKSMJLMH-UHFFFAOYSA-N 1,1-diethoxyethylbenzene Chemical compound CCOC(C)(OCC)C1=CC=CC=C1 BWZAUXRKSMJLMH-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-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
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 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
- 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
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
- NXBXJOWBDCQIHF-UHFFFAOYSA-N 2-[hydroxy-[2-(2-methylprop-2-enoyloxy)ethoxy]phosphoryl]oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(=O)OCCOC(=O)C(C)=C NXBXJOWBDCQIHF-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 1
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 229930183415 Suberin Natural products 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 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 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 150000001622 bismuth compounds Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVFSYZFXJYAPQJ-UHFFFAOYSA-N butyl(oxo)tin Chemical compound CCCC[Sn]=O BVFSYZFXJYAPQJ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- RWHJATFJJVMKGR-UHFFFAOYSA-L dibutyltin(2+);methanethioate Chemical compound [O-]C=S.[O-]C=S.CCCC[Sn+2]CCCC RWHJATFJJVMKGR-UHFFFAOYSA-L 0.000 description 1
- HNYIUBKOOFMIBM-UHFFFAOYSA-L dioctyltin(2+);methanethioate Chemical compound [O-]C=S.[O-]C=S.CCCCCCCC[Sn+2]CCCCCCCC HNYIUBKOOFMIBM-UHFFFAOYSA-L 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000001678 irradiating effect Effects 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
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JUYONNFUNDDKBE-UHFFFAOYSA-J tri(oct-2-enoyloxy)stannyl oct-2-enoate Chemical compound [Sn+4].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O JUYONNFUNDDKBE-UHFFFAOYSA-J 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
本発明は、接着性樹脂組成物及びそれを用いた接着材料に関し、特には金属酸化物、金属、樹脂等の種々の被着体に対する接着性に優れた、光硬化性の接着性樹脂組成物に関するものである。 The present invention relates to an adhesive resin composition and an adhesive material using the same, and in particular, a photocurable adhesive resin composition excellent in adhesiveness to various adherends such as metal oxides, metals and resins. It is about.
従来、電子部品、機械部品等を接着するための接着材料として、熱硬化性の接着材料が知られている。例えば、電子部品の接着のためには、異方性導電フィルム（ＡＣＦ）、異方性導電ペースト（ＡＣＰ）、非導電フィルム（ＮＣＦ）、非導電ペースト（ＮＣＰ）等の接着材料が使用されている。しかしながら、従来のＡＣＦ、ＡＣＰ、ＮＣＦ、ＮＣＰは、熱硬化性の接着材料であるため、高温処理を要する上、硬化に要する時間が長く、生産性が低下する問題がある。 Conventionally, thermosetting adhesive materials are known as adhesive materials for bonding electronic parts, machine parts, and the like. For example, adhesive materials such as anisotropic conductive film (ACF), anisotropic conductive paste (ACP), non-conductive film (NCF), and non-conductive paste (NCP) are used for bonding electronic components. Yes. However, since conventional ACF, ACP, NCF, and NCP are thermosetting adhesive materials, they require a high-temperature treatment and have a problem that the time required for curing is long and productivity is lowered.
一方、電子部品等の接着のために、光硬化性の接着材料が開発されており、該光硬化性の接着材料は、低温での光照射により極めて短時間で接着が完了するため、生産性を向上させることが可能である。 On the other hand, a photo-curable adhesive material has been developed for bonding electronic parts and the like, and the photo-curable adhesive material is completed in a very short time by light irradiation at a low temperature. It is possible to improve.
ところで、昨今の電子部品の組み立てにおいては、被着体として、金やニッケル等の金属、ＩＺＯやＩＴＯ等の金属酸化物、ＰＥＴやポリイミド等の樹脂を同時に接着する必要があるため、特定の被着体に対する接着性のみならず、種々の被着体に対する接着性に優れた接着材料が求められている。これに対して、本発明者らが検討したところ、従来の光硬化性の接着材料は、特定の被着体に対してのみ接着性が良好で、金等の金属、ＩＺＯ等の金属酸化物に対する接着性が悪いことが分かった。 By the way, in the recent assembly of electronic components, it is necessary to simultaneously adhere a metal such as gold or nickel, a metal oxide such as IZO or ITO, or a resin such as PET or polyimide as an adherend. There is a demand for an adhesive material having excellent adhesion to various adherends as well as adhesion to adherends. On the other hand, the present inventors have examined that a conventional photo-curing adhesive material has good adhesion only to a specific adherend and is a metal such as gold or a metal oxide such as IZO. It was found that the adhesiveness to was poor.
そこで、本発明の目的は、上記従来技術の問題を解決し、金属酸化物、金属、樹脂等の種々の被着体に対する接着性に優れた、光硬化性の接着性樹脂組成物及びそれを用いた接着剤材料を提供することにある。 Accordingly, an object of the present invention is to solve the above-mentioned problems of the prior art, and to provide a photocurable adhesive resin composition excellent in adhesiveness to various adherends such as metal oxides, metals, and resins, and the like. It is to provide an adhesive material used.
本発明者らは、上記目的を達成するために鋭意検討した結果、特定の(メタ)アクリレートオリゴマーと、特定の光重合性モノマーと、リン酸(メタ)アクリレートとを含む組成物が、金等の金属、ＩＺＯ等の金属酸化物、ＰＥＴ等の樹脂に対する接着性に優れることを見出し、本発明を完成させるに至った。 As a result of intensive studies to achieve the above object, the present inventors have found that a composition containing a specific (meth) acrylate oligomer, a specific photopolymerizable monomer, and phosphoric acid (meth) acrylate is gold or the like. The present invention was completed by finding excellent adhesion to metals such as IZO, metal oxides such as IZO, and resins such as PET.
即ち、本発明の接着性樹脂組成物は、
ウレタン(メタ)アクリレートオリゴマー（Ａ）と、
(メタ)アクリロイル基を有する環式モノマー（Ｂ）と、
リン酸(メタ)アクリレート（Ｃ）と
を含んでなることを特徴とする。
That is, the adhesive resin composition of the present invention is
Urethane (meth) acrylate oligomer (A),
A cyclic monomer (B) having a (meth) acryloyl group;
And phosphoric acid (meth) acrylate (C).
本発明の接着性樹脂組成物の好適例においては、前記リン酸(メタ)アクリレート（Ｃ）の添加量が、前記ウレタン(メタ)アクリレートオリゴマー（Ａ）と前記(メタ)アクリロイル基を有する環式モノマー（Ｂ）との合計100質量部に対して0.01〜3質量部の範囲である。 In a preferred example of the adhesive resin composition of the present invention, the amount of the phosphoric acid (meth) acrylate (C) added is a cyclic group having the urethane (meth) acrylate oligomer (A) and the (meth) acryloyl group. It is the range of 0.01-3 mass parts with respect to a total of 100 mass parts with a monomer (B).
本発明の接着性樹脂組成物は、更に、メラミン骨格を有する樹脂（Ｄ）を含むことが好ましい。ここで、該メラミン骨格を有する樹脂（Ｄ）の添加量は、前記ウレタン(メタ)アクリレートオリゴマー（Ａ）と前記(メタ)アクリロイル基を有する環式モノマー（Ｂ）との合計100質量部に対して0.5〜10質量部の範囲が好ましい。 The adhesive resin composition of the present invention preferably further contains a resin (D) having a melamine skeleton. Here, the addition amount of the resin (D) having the melamine skeleton is 100 parts by mass in total of the urethane (meth) acrylate oligomer (A) and the cyclic monomer (B) having the (meth) acryloyl group. The range of 0.5 to 10 parts by mass is preferred.
また、本発明の接着材料は、上記の接着性樹脂組成物を用いたことを特徴とし、該接着材料としては、ＡＣＦ、ＡＣＰ、ＮＣＦ、ＮＣＰが挙げられる。 The adhesive material of the present invention is characterized by using the above-mentioned adhesive resin composition, and examples of the adhesive material include ACF, ACP, NCF, and NCP.
本発明によれば、特定の(メタ)アクリレートオリゴマーと、特定の光重合性モノマーと、リン酸(メタ)アクリレートとを含み、金属酸化物、金属、樹脂等の種々の被着体に対する接着性に優れた光硬化性の接着性樹脂組成物、並びにそれを用いた接着剤材料を提供することができる。 According to the present invention, a specific (meth) acrylate oligomer, a specific photopolymerizable monomer, and phosphoric acid (meth) acrylate, and adhesion to various adherends such as metal oxides, metals, and resins. Can provide a photo-curable adhesive resin composition having excellent resistance, and an adhesive material using the same.
以下に、本発明を詳細に説明する。本発明の接着性樹脂組成物は、ウレタン(メタ)アクリレートオリゴマー（Ａ）と、(メタ)アクリロイル基を有する環式モノマー（Ｂ）と、リン酸(メタ)アクリレート（Ｃ）とを含んでなることを特徴とする。本発明の接着性樹脂組成物は、紫外線等の光を照射することで硬化するため、低温で且つ極めて短時間で接着を完了することができる上、ＩＺＯ等の金属酸化物、金等の金属、ＰＥＴ等の樹脂に対する接着性に優れる。なお、本発明の接着性樹脂組成物の使用に際し、光の照射条件は特に限定されず、適宜設定することができる。また、本発明の接着性樹脂組成物は、ウレタン(メタ)アクリレートオリゴマー（Ａ）及び(メタ)アクリロイル基を有する環式モノマー（Ｂ）に加え、リン酸(メタ)アクリレート（Ｃ）を含み、該リン酸(メタ)アクリレート（Ｃ）が従来の接着性に加え、更に金属系への接着性向上効果を発現するため、金属酸化物、金属、樹脂等の種々の被着体に対する接着性に非常に優れる。 The present invention is described in detail below. The adhesive resin composition of the present invention comprises a urethane (meth) acrylate oligomer (A), a cyclic monomer (B) having a (meth) acryloyl group, and phosphoric acid (meth) acrylate (C). It is characterized by that. The adhesive resin composition of the present invention is cured by irradiating light such as ultraviolet rays, so that the adhesion can be completed at a low temperature and in a very short time, and a metal oxide such as IZO and a metal such as gold Excellent adhesion to resins such as PET. In addition, when using the adhesive resin composition of this invention, the irradiation conditions of light are not specifically limited, It can set suitably. Further, the adhesive resin composition of the present invention contains a phosphoric acid (meth) acrylate (C) in addition to the urethane (meth) acrylate oligomer (A) and the cyclic monomer (B) having a (meth) acryloyl group, In addition to the conventional adhesiveness, the phosphoric acid (meth) acrylate (C) also exhibits the effect of improving the adhesion to metal systems, so that it can adhere to various adherends such as metal oxides, metals, and resins. Very good.
本発明の接着性樹脂組成物に用いるウレタン(メタ)アクリレートオリゴマー（Ａ）は、好ましくは、ウレタンアクリレートオリゴマーである。なお、ウレタン(メタ)アクリレートオリゴマー（Ａ）は、一種単独で用いてもよいし、二種以上を組み合わせて用いてもよい。接着性樹脂組成物がウレタン(メタ)アクリレートオリゴマー（Ａ）を含まない場合、光照射で形成される硬化物の破断強度及び破断伸びが低下し、硬化物の被着体への追従性が悪化して、接着が弱くなり、曲げや外部からの衝撃により、被着体同士が剥離し易くなる。 The urethane (meth) acrylate oligomer (A) used in the adhesive resin composition of the present invention is preferably a urethane acrylate oligomer. In addition, a urethane (meth) acrylate oligomer (A) may be used individually by 1 type, and may be used in combination of 2 or more type. When the adhesive resin composition does not contain the urethane (meth) acrylate oligomer (A), the breaking strength and breaking elongation of the cured product formed by light irradiation are lowered, and the followability of the cured product to the adherend is deteriorated. As a result, the adhesion becomes weak, and adherends are easily separated from each other by bending or external impact.
上記ウレタン(メタ)アクリレートオリゴマー（Ａ）は、(メタ)アクリロイルオキシ基［ＣＨ2＝ＣＨＣＯＯ−又はＣＨ2＝Ｃ(ＣＨ3)ＣＯＯ−］を１つ以上有し、ウレタン結合（−ＮＨＣＯＯ−）を複数有する化合物である。該ウレタン(メタ)アクリレートオリゴマー（Ａ）は、例えば、ポリオールとポリイソシアネートとからウレタンプレポリマーを合成し、該ウレタンプレポリマーに水酸基を有する(メタ)アクリレートを付加させることによって製造することができる。 The urethane (meth) acrylate oligomer (A) has at least one (meth) acryloyloxy group [CH 2 ═CHCOO— or CH 2 ═C (CH 3 ) COO—] and has a urethane bond (—NHCOO—). Is a compound having a plurality of The urethane (meth) acrylate oligomer (A) can be produced, for example, by synthesizing a urethane prepolymer from a polyol and a polyisocyanate, and adding a (meth) acrylate having a hydroxyl group to the urethane prepolymer.
上記ウレタンプレポリマーの合成に用いるポリオールは、水酸基を複数有する化合物であり、該ポリオールとして、具体的には、ポリエーテルポリオール、ポリエステルポリオール、ポリテトラメチレングリコール、ポリブタジエンポリオール、アルキレンオキサイド変性ポリブタジエンポリオール及びポリイソプレンポリオール等が挙げられる。なお、上記ポリエーテルポリオールは、例えば、エチレングリコール、プロピレングリコール、グリセリン等の多価アルコールに、エチレンオキシドやプロピレンオキシド等のアルキレンオキサイドを付加させて得られ、また、上記ポリエステルポリオールは、例えば、エチレングリコール、ジエチレングリコール、１,４-ブタンジオール、１,６-ヘキサンジオール、プロピレングリコール、トリメチロールエタン、トリメチロールプロパン等の多価アルコールと、アジピン酸、グルタル酸、コハク酸、セバシン酸、ピメリン酸、スベリン酸等の多価カルボン酸とから得られる。 The polyol used for the synthesis of the urethane prepolymer is a compound having a plurality of hydroxyl groups. Specific examples of the polyol include polyether polyol, polyester polyol, polytetramethylene glycol, polybutadiene polyol, alkylene oxide-modified polybutadiene polyol and polyoxypolyol. Examples include isoprene polyol. The polyether polyol is obtained, for example, by adding an alkylene oxide such as ethylene oxide or propylene oxide to a polyhydric alcohol such as ethylene glycol, propylene glycol, or glycerin. The polyester polyol is, for example, ethylene glycol. , Diethylene glycol, 1,4-butanediol, 1,6-hexanediol, propylene glycol, trimethylolethane, trimethylolpropane and other polyhydric alcohols and adipic acid, glutaric acid, succinic acid, sebacic acid, pimelic acid, suberin It is obtained from a polyvalent carboxylic acid such as an acid.
上記ポリイソシアネートは、イソシアネート基（ＮＣＯ基）を複数有する化合物であって、該ポリイソシアネートとして、具体的には、トリレンジイソシアネート（ＴＤＩ）、ジフェニルメタンジイソシアネート（ＭＤＩ）、粗製ジフェニルメタンジイソシアネート（クルードＭＤＩ）、イソホロンジイソシアネート（ＩＰＤＩ）、水素添加ジフェニルメタンジイソシアネート、水素添加トリレンジイソシアネート、ヘキサメチレンジイソシアネート（ＨＤＩ）や、これらのイソシアヌレート変性物、カルボジイミド変性物、グリコール変性物等が挙げられる。 The polyisocyanate is a compound having a plurality of isocyanate groups (NCO groups). Specifically, the polyisocyanate includes tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), crude diphenylmethane diisocyanate (crude MDI), Examples include isophorone diisocyanate (IPDI), hydrogenated diphenylmethane diisocyanate, hydrogenated tolylene diisocyanate, hexamethylene diisocyanate (HDI), these isocyanurate-modified products, carbodiimide-modified products, and glycol-modified products.
上記ウレタンプレポリマーの合成においては、ウレタン化反応用の触媒を用いることが好ましい。該ウレタン化反応用触媒としては、有機スズ化合物、無機スズ化合物、有機鉛化合物、モノアミン類、ジアミン類、トリアミン類、環状アミン類、アルコールアミン類、エーテルアミン類、有機スルホン酸、無機酸、チタン化合物、ビスマス化合物、四級アンモニウム塩等が挙げられ、これらの中でも、有機スズ化合物が好ましい。また、好適な有機スズ化合物としては、ジブチルスズジラウレート、ジブチルスズジアセテート、ジブチルスズチオカルボキシレート、ジブチルスズジマレエート、ジオクチルスズチオカルボキシレート、オクテン酸スズ、モノブチルスズオキシド等が挙げられる。 In the synthesis of the urethane prepolymer, it is preferable to use a catalyst for urethanization reaction. Examples of the catalyst for urethanization reaction include organic tin compounds, inorganic tin compounds, organic lead compounds, monoamines, diamines, triamines, cyclic amines, alcohol amines, ether amines, organic sulfonic acids, inorganic acids, titanium A compound, a bismuth compound, a quaternary ammonium salt, etc. are mentioned, Among these, an organotin compound is preferable. Suitable organic tin compounds include dibutyltin dilaurate, dibutyltin diacetate, dibutyltin thiocarboxylate, dibutyltin dimaleate, dioctyltin thiocarboxylate, tin octenoate, monobutyltin oxide, and the like.
また、上記ウレタンプレポリマーに付加させる水酸基を有する(メタ)アクリレートは、水酸基を１つ以上有し、(メタ)アクリロイルオキシ基を１つ以上有する化合物である。該水酸基を有する(メタ)アクリレートは、上記ウレタンプレポリマーのイソシアネート基に付加することができる。該水酸基を有する(メタ)アクリレートとしては、２-ヒドロキシエチル(メタ)アクリレート、２-ヒドロキシプロピル(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート等が挙げられる。 The (meth) acrylate having a hydroxyl group to be added to the urethane prepolymer is a compound having one or more hydroxyl groups and one or more (meth) acryloyloxy groups. The (meth) acrylate having a hydroxyl group can be added to the isocyanate group of the urethane prepolymer. Examples of the (meth) acrylate having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and pentaerythritol tri (meth) acrylate.
本発明の接着性樹脂組成物に用いる(メタ)アクリロイル基を有する環式モノマー（Ｂ）は、アクリロイル基を有する環式モノマーであることが好ましい。なお、(メタ)アクリロイル基を有する環式モノマー（Ｂ）は、一種単独で用いてもよいし、二種以上を組み合わせて用いてもよい。接着性樹脂組成物が(メタ)アクリロイル基を有する環式モノマー（Ｂ）を含まない場合、多種の被着体への接着性、特に樹脂、金属酸化物への接着性が得られ難い。これは、理由は明確ではないが、モルフォリノ基等の極性基が接着に大きく関与しているためと考えられる。 The cyclic monomer (B) having a (meth) acryloyl group used in the adhesive resin composition of the present invention is preferably a cyclic monomer having an acryloyl group. In addition, the cyclic monomer (B) which has a (meth) acryloyl group may be used individually by 1 type, and may be used in combination of 2 or more type. When the adhesive resin composition does not contain the cyclic monomer (B) having a (meth) acryloyl group, it is difficult to obtain adhesiveness to various adherends, particularly adhesiveness to resins and metal oxides. Although the reason is not clear, it is considered that polar groups such as morpholino groups are greatly involved in adhesion.
上記(メタ)アクリロイル基を有する環式モノマー（Ｂ）は、環を１つ以上有し、(メタ)アクリロイル基［ＣＨ2＝ＣＨＣＯ−又はＣＨ2＝Ｃ(ＣＨ3)ＣＯ−］を１つ以上有する化合物である。ここで、環としては、モルホリン環、トリアジン環、イソボルニル、ベンゼン環等が挙げられ、これらの中でも、モルホリン環等の複素環が好ましい。また、(メタ)アクリロイル基を有する環式モノマーとして、具体的には、(メタ)アクリロイルモルホリン等が挙げられ、アクリロイルモルホリンが好ましい。 The cyclic monomer (B) having the (meth) acryloyl group has one or more rings and one (meth) acryloyl group [CH 2 ═CHCO— or CH 2 ═C (CH 3 ) CO—]. It is a compound having the above. Here, examples of the ring include morpholine ring, triazine ring, isobornyl, benzene ring and the like, and among these, a heterocyclic ring such as morpholine ring is preferable. Specific examples of the cyclic monomer having a (meth) acryloyl group include (meth) acryloylmorpholine, and acryloylmorpholine is preferred.
本発明の接着性樹脂組成物において、上記ウレタン(メタ)アクリレートオリゴマー（Ａ）の上記(メタ)アクリロイル基を有する環式モノマー（Ｂ）に対する質量比（Ａ／Ｂ）は、85／15〜30／70の範囲が好ましい。ウレタン(メタ)アクリレートオリゴマー（Ａ）と(メタ)アクリロイル基を有する環式モノマー（Ｂ）との総量に占めるウレタン(メタ)アクリレートオリゴマー（Ａ）の割合が85質量％を超えると（即ち、(メタ)アクリロイル基を有する環式モノマー（Ｂ）の割合が15質量％未満では）、(メタ)アクリロイル基を有する環式モノマー（Ｂ）が含有する接着に関与する官能基量が不十分で、接着強度が低下し、また、高粘度化により、取り扱いが困難になるといった問題も生じる。また、ウレタン(メタ)アクリレートオリゴマー（Ａ）の割合が30質量％未満でも（即ち、(メタ)アクリロイル基を有する環式モノマー（Ｂ）の割合が70質量％を超えても）、硬化収縮が大きいことや、ウレタン(メタ)アクリレートオリゴマー（Ａ）由来の接着発現機能が不十分となるため、接着強度が低下する。 In the adhesive resin composition of the present invention, the mass ratio (A / B) of the urethane (meth) acrylate oligomer (A) to the cyclic monomer (B) having the (meth) acryloyl group is from 85/15 to 30. A range of / 70 is preferred. When the proportion of the urethane (meth) acrylate oligomer (A) in the total amount of the urethane (meth) acrylate oligomer (A) and the cyclic monomer (B) having a (meth) acryloyl group exceeds 85% by mass (that is, ( When the ratio of the cyclic monomer (B) having a (meth) acryloyl group is less than 15% by mass), the amount of the functional group involved in the adhesion contained in the cyclic monomer (B) having a (meth) acryloyl group is insufficient, Adhesive strength is lowered, and there is a problem that handling becomes difficult due to increased viscosity. Further, even when the proportion of the urethane (meth) acrylate oligomer (A) is less than 30% by mass (that is, even when the proportion of the cyclic monomer (B) having a (meth) acryloyl group exceeds 70% by mass), the curing shrinkage is caused. Adhesive strength is lowered because the adhesion development function derived from the large size and the urethane (meth) acrylate oligomer (A) is insufficient.
本発明の接着性樹脂組成物に用いるリン酸(メタ)アクリレート（Ｃ）は、(メタ)アクリロイルオキシ基を１つ以上有するリン酸エステルであり、モノエステルでも、ジエステルでも、トリエステルでもよいが、モノエステル又はジエステルであることが好ましい。該リン酸(メタ)アクリレート（Ｃ）として、具体的には、２-(メタ)アクリロイロキシエチルアシッドホスフェート、ジ-２-(メタ)アクリロイロキシエチルアシッドホスフェート、３-(メタ)アクリロイロキシプロピルアシッドホスフェート、ジ-３-(メタ)アクリロイロキシプロピルアシッドホスフェート等が挙げられる。これらリン酸(メタ)アクリレート（Ｃ）は、１種単独で用いてもよいし、２種以上を組み合わせて用いてもよい。 The phosphoric acid (meth) acrylate (C) used in the adhesive resin composition of the present invention is a phosphate ester having one or more (meth) acryloyloxy groups, and may be a monoester, a diester, or a triester. , Monoester or diester. As the phosphoric acid (meth) acrylate (C), specifically, 2- (meth) acryloyloxyethyl acid phosphate, di-2- (meth) acryloyloxyethyl acid phosphate, 3- (meth) acryloyl Examples include loxypropyl acid phosphate, di-3- (meth) acryloyloxypropyl acid phosphate, and the like. These phosphoric acid (meth) acrylates (C) may be used alone or in combination of two or more.
上記リン酸(メタ)アクリレート（Ｃ）の添加量は、上記ウレタン(メタ)アクリレートオリゴマー（Ａ）と(メタ)アクリロイル基を有する環式モノマー（Ｂ）との合計100質量部に対して0.01〜3質量部の範囲が好ましい。リン酸(メタ)アクリレート（Ｃ）の添加量が0.01質量部未満では、各種被着体に対する接着性を向上させる効果が小さく、一方、3質量部を超えると、電極材料として用いられるＩＺＯを腐食する恐れがある。 The addition amount of the phosphoric acid (meth) acrylate (C) is 0.01 to 100 parts by mass with respect to a total of 100 parts by mass of the urethane (meth) acrylate oligomer (A) and the cyclic monomer (B) having a (meth) acryloyl group. A range of 3 parts by weight is preferred. When the addition amount of phosphoric acid (meth) acrylate (C) is less than 0.01 parts by mass, the effect of improving the adhesion to various adherends is small, while when it exceeds 3 parts by mass, IZO used as an electrode material is corroded. There is a fear.
本発明の接着性樹脂組成物は、更に、メラミン骨格を有する樹脂（Ｄ）を含むことが好ましい。接着性樹脂組成物がメラミン骨格を有する樹脂（Ｄ）を含む場合、各種被着体に対する接着性が更に向上する。ここで、メラミン骨格を有する樹脂（Ｄ）として、具体的には、メラミン樹脂、メチル化メラミン樹脂、イソブチル化メラミン樹脂、ｎ−ブチル化メラミン樹脂等のブチル化メラミン樹脂、ブチル／メチル化メラミン樹脂等が挙げられる。これらメラミン系樹脂（Ｄ）は、１種単独で用いてもよいし、２種以上を組み合わせて用いてもよい。 The adhesive resin composition of the present invention preferably further contains a resin (D) having a melamine skeleton. When the adhesive resin composition contains a resin (D) having a melamine skeleton, the adhesion to various adherends is further improved. Here, as the resin (D) having a melamine skeleton, specifically, butylated melamine resins such as melamine resin, methylated melamine resin, isobutylated melamine resin, n-butylated melamine resin, and butyl / methylated melamine resin Etc. These melamine resins (D) may be used singly or in combination of two or more.
上記メラミン骨格を有する樹脂（Ｄ）の添加量は、上記ウレタン(メタ)アクリレートオリゴマー（Ａ）と(メタ)アクリロイル基を有する環式モノマー（Ｂ）との合計100質量部に対して0.5〜10質量部の範囲が好ましい。メラミン骨格を有する樹脂（Ｄ）の添加量が0.5質量部未満では、各種被着体に対する接着性を向上させる効果が小さく、一方、10質量部を超えても、接着向上の差異が現れず、更には本来の組成物の割合が少なくなり、接着性がかえって損なわれる。 The addition amount of the resin (D) having the melamine skeleton is 0.5 to 10 with respect to a total of 100 parts by mass of the urethane (meth) acrylate oligomer (A) and the cyclic monomer (B) having a (meth) acryloyl group. A range of parts by mass is preferred. If the addition amount of the resin (D) having a melamine skeleton is less than 0.5 parts by mass, the effect of improving the adhesion to various adherends is small, while if it exceeds 10 parts by mass, no difference in adhesion improvement appears, Furthermore, the proportion of the original composition is reduced and the adhesiveness is rather impaired.
本発明の接着性樹脂組成物は、更に光重合開始剤（Ｅ）を含むことが好ましく、この場合、紫外線等の光の照射によって、接着性樹脂組成物を容易に硬化させることができる。該光重合開始剤（Ｅ）は、光を照射されることによって、上述したウレタン(メタ)アクリレートオリゴマー（Ａ）や(メタ)アクリロイル基を有する環式モノマー（Ｂ）の重合を開始させる作用を有する。該光重合開始剤（Ｅ）としては、４-ジメチルアミノ安息香酸、４-ジメチルアミノ安息香酸エステル、２,２-ジメトキシ-２-フェニルアセトフェノン、アセトフェノンジエチルケタール、アルコキシアセトフェノン、ベンジルジメチルケタール、ベンゾフェノン及び３,３-ジメチル-４-メトキシベンゾフェノン、４,４-ジメトキシベンゾフェノン、４,４-ジアミノベンゾフェノン等のベンゾフェノン誘導体、ベンゾイル安息香酸アルキル、ビス(４-ジアルキルアミノフェニル)ケトン、ベンジル及びベンジルメチルケタール等のベンジル誘導体、ベンゾイン及びベンゾインイソブチルエーテル等のベンゾイン誘導体、ベンゾインイソプロピルエーテル、２-ヒドロキシ-２-メチルプロピオフェノン、１-ヒドロキシ-シクロヘキシル-フェニル-ケトン、キサントン、チオキサントン及びチオキサントン誘導体、フルオレン、２,４,６-トリメチルベンゾイルジフェニルホスフィンオキシド、ビス(２,６-ジメトキシベンゾイル)-２,４,４-トリメチルペンチルホスフィンオキシド、ビス(２,４,６-トリメチルベンゾイル)-フェニルホスフィンオキシド、２-メチル-１-(４-メチルチオフェニル)-２-モルホリノプロパン-１-オン、２-ベンジル-２-ジメチルアミノ-１-(モルホリノフェニル)-ブタノン-１等が挙げられる。これら光重合開始剤（Ｅ）は、１種を単独で用いてもよいし、２種以上を組み合わせて使用してもよい。 The adhesive resin composition of the present invention preferably further contains a photopolymerization initiator (E). In this case, the adhesive resin composition can be easily cured by irradiation with light such as ultraviolet rays. The photopolymerization initiator (E) has an action of initiating polymerization of the above-described urethane (meth) acrylate oligomer (A) or the cyclic monomer (B) having a (meth) acryloyl group when irradiated with light. Have. Examples of the photopolymerization initiator (E) include 4-dimethylaminobenzoic acid, 4-dimethylaminobenzoic acid ester, 2,2-dimethoxy-2-phenylacetophenone, acetophenone diethyl ketal, alkoxyacetophenone, benzyldimethyl ketal, benzophenone and 3,3-dimethyl-4-methoxybenzophenone, benzophenone derivatives such as 4,4-dimethoxybenzophenone, 4,4-diaminobenzophenone, alkyl benzoylbenzoate, bis (4-dialkylaminophenyl) ketone, benzyl, benzylmethyl ketal, etc. Benzyl derivatives, benzoin derivatives such as benzoin and benzoin isobutyl ether, benzoin isopropyl ether, 2-hydroxy-2-methylpropiophenone, 1-hydroxy-cyclohexyl-phenyl-ketone, Thiolene, thioxanthone and thioxanthone derivatives, fluorene, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis (2,4,6- Trimethylbenzoyl) -phenylphosphine oxide, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (morpholinophenyl) -butanone-1, etc. Is mentioned. These photoinitiators (E) may be used individually by 1 type, and may be used in combination of 2 or more type.
本発明の接着性樹脂組成物における上記光重合開始剤（Ｅ）の配合量は、上記ウレタン(メタ)アクリレートオリゴマー（Ａ）と上記(メタ)アクリロイル基を有する環式モノマー（Ｂ）との合計100質量部に対して0.1〜10質量部の範囲が好ましい。光重合開始剤（Ｅ）の配合量が0.1質量部未満では、接着性樹脂組成物の光硬化を開始させる効果が小さく、一方、10質量部を超えると、光硬化を開始させる効果が飽和する一方、接着性樹脂組成物の原料コストが高くなり、また、残留開始剤による変色、劣化等も起こる。 The blending amount of the photopolymerization initiator (E) in the adhesive resin composition of the present invention is the sum of the urethane (meth) acrylate oligomer (A) and the cyclic monomer (B) having the (meth) acryloyl group. The range of 0.1-10 mass parts is preferable with respect to 100 mass parts. When the blending amount of the photopolymerization initiator (E) is less than 0.1 parts by mass, the effect of initiating photocuring of the adhesive resin composition is small. On the other hand, when it exceeds 10 parts by mass, the effect of initiating photocuring is saturated. On the other hand, the raw material cost of the adhesive resin composition is increased, and discoloration and deterioration due to the residual initiator also occur.
上述のように、本発明の接着性樹脂組成物は、ＩＺＯ等の金属酸化物、金等の金属、ＰＥＴ等の樹脂に対する接着性に優れる。そのため、本発明の接着性樹脂組成物は、これら様々な被着体の接着に好適に利用することができ、より具体的には、異方性導電フィルム（ＡＣＦ）、異方性導電ペースト（ＡＣＰ）、非導電フィルム（ＮＣＦ）、非導電ペースト（ＮＣＰ）等の電子部材用接着材料として有用である。 As described above, the adhesive resin composition of the present invention is excellent in adhesion to metal oxides such as IZO, metals such as gold, and resins such as PET. Therefore, the adhesive resin composition of the present invention can be suitably used for adhesion of these various adherends. More specifically, an anisotropic conductive film (ACF), an anisotropic conductive paste ( It is useful as an adhesive material for electronic members such as ACP), non-conductive film (NCF), and non-conductive paste (NCP).
以下に、実施例を挙げて本発明を更に詳しく説明するが、本発明は下記の実施例に何ら限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples.
表１に示す配合の接着性樹脂組成物を調製し、下記の方法で各被着体（ＰＥＴ：東レ製「ルミラーＴ６０」、ＩＺＯ：帝人製「ＨＰ１２５ＣＣ−Ｂ２００」、Ａｕ：丸和製作所製ＦＰＣ用金蒸着フィルム）に対する接着強度を測定した。結果を表１に示す。 An adhesive resin composition having the composition shown in Table 1 was prepared, and each adherend (PET: “Lumirror T60” manufactured by Toray, IZO: “HP125CC-B200” manufactured by Teijin, Inc.), Au: FPC manufactured by Maruwa Manufacturing Co., Ltd. The adhesion strength to the gold-deposited film was measured. The results are shown in Table 1.
＜各被着体に対する接着強度の測定方法＞
（１）各対照基材に50μmの厚みになるように接着性樹脂組成物を塗布し、（２）その上に、易接着ＰＥＴ：０３ＬＦ８を裏打ち材として挟み込み、（３）易接着ＰＥＴの上から、700 mW/cm2の照射強度でＵＶを照射して、サンプルを作製し、その後、（４）ＪＩＳ Ｋ６８５４−２に則って、剥離試験を行った。
<Measurement method of adhesive strength to each adherend>
(1) Adhesive resin composition was applied to each control substrate so as to have a thickness of 50 μm, (2) Easy adhesion PET: 03LF8 was sandwiched as a backing material, and (3) Easy adhesion PET Then, UV was irradiated at an irradiation intensity of 700 mW / cm 2 to prepare a sample, and then (4) a peel test was performed in accordance with JIS K6854-2.
*1 日本合成化学製, 商品名「ＵＶ３７００Ｂ」, ウレタンアクリレートオリゴマー
*2 新中村化学製, 商品名「ＡＭＯ」, アクリロイルモルホリン
*3 共栄社化学製, 商品名「Ｐ１Ｍ」, ２-メタクリロイロキシエチルアシッドホスフェート
*4 共栄社化学製, 商品名「Ｐ２Ｍ」, ジ-２-メタクリロイロキシエチルアシッドホスフェート
*5 共栄社化学製, 商品名「Ｐ１Ａ」, ２-アクリロイロキシエチルアシッドホスフェート
*6 日本サイテックインダストリーズ製, 商品名「ＳＹ２３２」, ブチル／メチル化メラミン樹脂
*7 大日本インキ製, 商品名「Ｌ１４５」, イソブチル化メラミン樹脂
*8 チバ・スペシャルティ・ケミカルズ製, 商品名「ＩＲＧ １８４Ｄ」, ヒドロキシアセトフェノン
* 1 Nippon Synthetic Chemical Co., Ltd., trade name “UV3700B”, urethane acrylate oligomer
* 2 Shin-Nakamura Chemical Co., Ltd., trade name “AMO”, acryloylmorpholine
* 3 Kyoeisha Chemical Co., Ltd., trade name “P1M”, 2-methacryloyloxyethyl acid phosphate
* 4 Kyoeisha Chemical Co., Ltd., trade name “P2M”, di-2-methacryloyloxyethyl acid phosphate
* 5 Kyoeisha Chemical Co., Ltd., trade name “P1A”, 2-acryloyloxyethyl acid phosphate
* 6 Made by Nippon Cytec Industries, trade name “SY232”, butyl / methylated melamine resin
* 7 Dainippon Ink, trade name “L145”, isobutylated melamine resin
* 8 Ciba Specialty Chemicals, trade name “IRG 184D”, hydroxyacetophenone
表１から、ウレタン(メタ)アクリレートオリゴマー（Ａ）と、(メタ)アクリロイル基を有する環式モノマー（Ｂ）と、リン酸(メタ)アクリレート（Ｃ）とを含む実施例の組成物が、金、ＩＺＯ及びＰＥＴに対する接着性に優れることが分かる。 From Table 1, the composition of the Example containing urethane (meth) acrylate oligomer (A), the cyclic monomer (B) which has a (meth) acryloyl group, and phosphoric acid (meth) acrylate (C) is gold | metal | money. It can be seen that it has excellent adhesion to IZO and PET.
Claims (5)
(メタ)アクリロイル基を有する環式モノマー（Ｂ）と、
リン酸(メタ)アクリレート（Ｃ）と
を含んでなる接着性樹脂組成物。 Urethane (meth) acrylate oligomer (A),
A cyclic monomer (B) having a (meth) acryloyl group;
An adhesive resin composition comprising phosphoric acid (meth) acrylate (C).
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012077329A1 (en) * | 2010-12-08 | 2012-06-14 | 株式会社ブリヂストン | Adhesive composition |
| JP5594359B2 (en) * | 2010-03-25 | 2014-09-24 | 日立化成株式会社 | Adhesive composition and use thereof, circuit member connection structure, and manufacturing method thereof |
| WO2014208518A1 (en) * | 2013-06-24 | 2014-12-31 | 大日本印刷株式会社 | Resin composition |
| JP7406040B1 (en) | 2023-10-11 | 2023-12-26 | サカタインクス株式会社 | Active energy ray curable adhesive composition |
| US20250136819A1 (en) * | 2022-10-25 | 2025-05-01 | Sun Chemical Corporation | Primers for energy-curable inks and coatings on metallized substrates |
-
2007
- 2007-11-07 JP JP2007289601A patent/JP2009114352A/en not_active Withdrawn
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5594359B2 (en) * | 2010-03-25 | 2014-09-24 | 日立化成株式会社 | Adhesive composition and use thereof, circuit member connection structure, and manufacturing method thereof |
| WO2012077329A1 (en) * | 2010-12-08 | 2012-06-14 | 株式会社ブリヂストン | Adhesive composition |
| WO2014208518A1 (en) * | 2013-06-24 | 2014-12-31 | 大日本印刷株式会社 | Resin composition |
| US10005937B2 (en) | 2013-06-24 | 2018-06-26 | Dai Nippon Printing Co., Ltd. | Resin composition |
| US20250136819A1 (en) * | 2022-10-25 | 2025-05-01 | Sun Chemical Corporation | Primers for energy-curable inks and coatings on metallized substrates |
| JP7406040B1 (en) | 2023-10-11 | 2023-12-26 | サカタインクス株式会社 | Active energy ray curable adhesive composition |
| JP2025066313A (en) * | 2023-10-11 | 2025-04-23 | サカタインクス株式会社 | Active energy ray curable adhesive composition |
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