JPWO2017221694A1 - 接着剤組成物 - Google Patents
接着剤組成物 Download PDFInfo
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- JPWO2017221694A1 JPWO2017221694A1 JP2018523682A JP2018523682A JPWO2017221694A1 JP WO2017221694 A1 JPWO2017221694 A1 JP WO2017221694A1 JP 2018523682 A JP2018523682 A JP 2018523682A JP 2018523682 A JP2018523682 A JP 2018523682A JP WO2017221694 A1 JPWO2017221694 A1 JP WO2017221694A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 106
- 239000000853 adhesive Substances 0.000 title claims abstract description 72
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 239000003054 catalyst Substances 0.000 claims abstract description 88
- 229920005989 resin Polymers 0.000 claims abstract description 82
- 239000011347 resin Substances 0.000 claims abstract description 82
- 229910052736 halogen Chemical group 0.000 claims abstract description 43
- 150000002367 halogens Chemical group 0.000 claims abstract description 43
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims description 114
- -1 acryl Chemical group 0.000 claims description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 abstract description 42
- 238000000034 method Methods 0.000 abstract description 26
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- 125000004429 atom Chemical group 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 150000003254 radicals Chemical class 0.000 description 43
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 36
- 229910052751 metal Inorganic materials 0.000 description 32
- 239000002184 metal Substances 0.000 description 32
- 229920000768 polyamine Polymers 0.000 description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 19
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- 239000000758 substrate Substances 0.000 description 17
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- 238000004519 manufacturing process Methods 0.000 description 8
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- 150000001412 amines Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
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- 239000011572 manganese Substances 0.000 description 5
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
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- VMGSQCIDWAUGLQ-UHFFFAOYSA-N n',n'-bis[2-(dimethylamino)ethyl]-n,n-dimethylethane-1,2-diamine Chemical compound CN(C)CCN(CCN(C)C)CCN(C)C VMGSQCIDWAUGLQ-UHFFFAOYSA-N 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
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- 230000000379 polymerizing effect Effects 0.000 description 4
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 3
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004641 Diallyl-phthalate Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GOKIPOOTKLLKDI-UHFFFAOYSA-N acetic acid;iron Chemical compound [Fe].CC(O)=O.CC(O)=O.CC(O)=O GOKIPOOTKLLKDI-UHFFFAOYSA-N 0.000 description 3
- 125000004018 acid anhydride group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
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- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- LRIOGIBXOOAGMT-UHFFFAOYSA-N n'-(2-aminoethyl)ethane-1,2-diamine;triethylborane Chemical compound CCB(CC)CC.NCCNCCN LRIOGIBXOOAGMT-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- IJUCBZFJEAVADL-UHFFFAOYSA-N propane-1,3-diamine;triethylborane Chemical compound NCCCN.CCB(CC)CC IJUCBZFJEAVADL-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000001302 tertiary amino group Chemical group 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ZPBJLEZUJMQIHC-UHFFFAOYSA-N 2-(2-bromo-2-methylpropanoyl)oxyethyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C(=O)OCCOC(=O)C(C)(C)Br ZPBJLEZUJMQIHC-UHFFFAOYSA-N 0.000 description 2
- YOCIJWAHRAJQFT-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl bromide Chemical compound CC(C)(Br)C(Br)=O YOCIJWAHRAJQFT-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- 125000003277 amino group Chemical group 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
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- 238000000576 coating method Methods 0.000 description 2
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
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- PQQAOTNUALRVTE-UHFFFAOYSA-L iron(2+);diformate Chemical compound [Fe+2].[O-]C=O.[O-]C=O PQQAOTNUALRVTE-UHFFFAOYSA-L 0.000 description 2
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- 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
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- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- HRFJEOWVAGSJNW-UHFFFAOYSA-N 1,4,8,11-tetramethyl-1,4,8,11-tetrazacyclotetradecane Chemical compound CN1CCCN(C)CCN(C)CCCN(C)CC1 HRFJEOWVAGSJNW-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
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- VGUWFGWZSVLROP-UHFFFAOYSA-N 1-pyridin-2-yl-n,n-bis(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CN(CC=1N=CC=CC=1)CC1=CC=CC=N1 VGUWFGWZSVLROP-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- SMSVUYQRWYTTLI-UHFFFAOYSA-L 2-ethylhexanoate;iron(2+) Chemical compound [Fe+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O SMSVUYQRWYTTLI-UHFFFAOYSA-L 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- MWDGNKGKLOBESZ-UHFFFAOYSA-N 2-oxooctanal Chemical compound CCCCCCC(=O)C=O MWDGNKGKLOBESZ-UHFFFAOYSA-N 0.000 description 1
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical group CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 1
- TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical group CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004801 Chlorinated PVC Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CVRXLMUYFMERMJ-UHFFFAOYSA-N N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine Chemical compound C=1C=CC=NC=1CN(CC=1N=CC=CC=1)CCN(CC=1N=CC=CC=1)CC1=CC=CC=N1 CVRXLMUYFMERMJ-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000004830 Super Glue Substances 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 239000007874 V-70 Substances 0.000 description 1
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- 150000008065 acid anhydrides Chemical class 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
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- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-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
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical group BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- YYACIIYHJXWXJE-UHFFFAOYSA-L copper(1+);2-ethylhexanoate Chemical compound [Cu+].[Cu+].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O YYACIIYHJXWXJE-UHFFFAOYSA-L 0.000 description 1
- FSGSLHGEFPNBBN-UHFFFAOYSA-M copper(1+);formate Chemical compound [Cu+].[O-]C=O FSGSLHGEFPNBBN-UHFFFAOYSA-M 0.000 description 1
- FPHREELHOCEQEA-UHFFFAOYSA-M copper(1+);octadecanoate Chemical compound [Cu+].CCCCCCCCCCCCCCCCCC([O-])=O FPHREELHOCEQEA-UHFFFAOYSA-M 0.000 description 1
- GDFGBZPSSUEBJH-UHFFFAOYSA-L copper(1+);oxalate Chemical compound [Cu+].[Cu+].[O-]C(=O)C([O-])=O GDFGBZPSSUEBJH-UHFFFAOYSA-L 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 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
- 230000006866 deterioration Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- FESAXEDIWWXCNG-UHFFFAOYSA-N diethyl(methoxy)borane Chemical compound CCB(CC)OC FESAXEDIWWXCNG-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 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
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- 125000004185 ester group Chemical group 0.000 description 1
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- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- FRVCGRDGKAINSV-UHFFFAOYSA-L iron(2+);octadecanoate Chemical compound [Fe+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O FRVCGRDGKAINSV-UHFFFAOYSA-L 0.000 description 1
- OWZIYWAUNZMLRT-UHFFFAOYSA-L iron(2+);oxalate Chemical compound [Fe+2].[O-]C(=O)C([O-])=O OWZIYWAUNZMLRT-UHFFFAOYSA-L 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-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
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000007882 oil-soluble azo polymerization initiator Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- YNXCGLKMOXLBOD-UHFFFAOYSA-N oxolan-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CCCO1 YNXCGLKMOXLBOD-UHFFFAOYSA-N 0.000 description 1
- 238000009840 oxygen flask method Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011941 photocatalyst Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 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
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- NMHWWOSZMMORNT-UHFFFAOYSA-N trihexylborane Chemical compound CCCCCCB(CCCCCC)CCCCCC NMHWWOSZMMORNT-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J127/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Adhesives based on derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
[2] 樹脂(A)のハロゲン含有量が30質量%以上である、[1]に記載の接着剤組成物。
[4] 前記重合性不飽和基を有する化合物(B)が、(メタ)アクリルモノマーを含む、[1]〜[3]のいずれかに記載の接着剤組成物。
本発明の組成物は、以下で説明する特定の構造を有する樹脂(A)(以下、単に「樹脂(A)」ともいう)、重合性不飽和基を有する化合物(B)(以下、単に「化合物(B)」ともいう)、およびラジカル硬化触媒(C)を含む。本発明の組成物は、必要に応じて、さらに他の成分を含んでもよい。
樹脂(A)は、下記式(1)で表される構造とニトリル基とを有する。
本発明の接着剤組成物は、重合性不飽和基を有する化合物(B)を含む。本発明の接着剤組成物は、前記化合物(B)が重合することにより、基材等を接着することができる。
本発明の接着剤組成物は、ラジカル硬化触媒(C)を含む。
オルガノボラン−アミン錯体およびカルボニル化合物の組み合わせは特に制限されないが、硬化触媒(C2)としては、例えば、トリエチルボラン−1,3−ジアミノプロパン錯体および酢酸を含む硬化触媒、トリエチルボラン−1,3−ジアミノプロパン錯体およびグルタル酸を含む硬化触媒、トリエチルボラン−1,3−ジアミノプロパン錯体および無水コハク酸を含む硬化触媒、トリエチルボラン−ジエチレントリアミン錯体および酢酸を含む硬化触媒、トリエチルボラン−ジエチレントリアミン錯体およびグルタル酸を含む硬化触媒、トリエチルボラン−ジエチレントリアミン錯体および無水コハク酸を含む硬化触媒が挙げられる。
本発明の組成物は、低表面エネルギー基材と、異種材料との接着性を向上させるために、シランカップリング剤を含んでいてもよい。本発明の組成物は、樹脂(A)と化合物(B)と合計100質量部に対して、シランカップリング剤を1〜5質量部含有すると、より異種材料との接着性が向上するため好ましい。
本発明の組成物は、さらに必要に応じて、他の成分を含んでもよい。
本発明の組成物は、樹脂(A)を3〜45質量部、化合物(B)を55〜97質量部、およびラジカル硬化触媒(C)を0.5〜15質量部含み、前記樹脂(A)と化合物(B)との合計が100質量部である。
特開平7−316233号公報を参考に、塩化ビニリデン・アクリロニトリル共重合物の合成を、以下の方法で行った。
塩化ビニリデン・アクリロニトリル共重合物について、ゲルパーミエーションクロマトグラフィー法により、下記条件でMwおよびMw/Mnを求めた。
・測定装置:HLC−8320GPC(東ソー(株)製)
・GPCカラム構成:以下の4連カラム(すべて東ソー(株)製)
(1)TSKgel HxL−H(ガードカラム)
(2)TSKgel GMHxL
(3)TSKgel GMHxL
(4)TSKgel G2500HxL
・流速:1.0mL/min
・カラム温度:40℃
・サンプル濃度:1.5%(w/v)(テトラヒドロフランで希釈)
・移動相溶媒:テトラヒドロフラン
・標準ポリスチレン換算
表1、2に記載の処方となるように、樹脂、重合性不飽和基を有する化合物(B)それぞれを計量し、ガラス製の容器に投入した。その後、各成分が均一に溶解するまで10分程度混ぜ、接着剤主剤を調製した。
各実施例、比較例で得られた接着剤組成物それぞれについて、以下のように評価した。
得られた接着剤組成物および、基材としてポリプロピレンシート(25mm×100mm×1.6mm厚)(2枚)を用い、JIS K 6850(引張せん断接着強さ)に基づき、貼り合せ面が25mm×12.5mm、接着樹脂層の厚さが50μmとなる様に、一方の基材に接着剤組成物を塗布し、もう一方の基材と貼り合わせ、23℃50%RHにて24hr静置し、サンプルを作製した。
基材と張り合わせた後、60℃で5hr静置後、23℃50%RHにて24hr静置する以外は、「実施例1〜15、比較例1〜3、5〜14で得た接着剤組成物を用いたサンプルの作製」の項と同様に行い、サンプルを作製した。
基材と貼り合わせた後、被着体ポリプロピレンシートに紫外線照射を、紫外線照射装置(JATEC製、ピーク波長365nm)を用いて150mvにて20分行い、続いて23℃50%RHにて24hr静置する以外は、「実施例1〜15、比較例1〜3、5〜14で得た接着剤組成物を用いたサンプルの作製」の項と同様に行い、サンプルを作製した。
基材の一方をSUS(ステンレス鋼、25mm×150mm×2.0mm厚)に変更した以外は、「実施例1〜15、比較例1〜3、5〜14で得た接着剤組成物を用いたサンプルの作製」の項と同様に行い、サンプルを作製した。
接着剤組成物を調製後、接着剤組成物が増粘し、ゲル化した。このため、基材であるポリプロピレンシートに接着剤組成物を塗布することができず、サンプルを作製することができなかった。
上記方法で得られたサンプルについて、引張せん断接着強度を測定した。
なお、各実施例、比較例で使用した成分は以下の通りである。
・塩化ビニリデン・アクリロニトリル共重合物:前記合成例1で得られた塩化ビニリデン・アクリロニトリル共重合物、塩素含有量(ハロゲン含有量)59質量%、ニトリル基含有量3.8×10-3mol/g
・アクリロニトリル・ブタジエン共重合物:日本ゼオン株式会社製、Nipol1001CG、ハロゲン含有量0質量%、ニトリル基含有量7.6×10-3mol/g
・塩素化ポリエチレン:昭和電工株式会社製、エラスレン353A、塩素含有量35質量%、ニトリル基含有量0mol/g
・クロロスルホン化ポリエチレン:東ソー株式会社製、TOSO−CSM CS340、塩素含有量43質量%、ニトリル基含有量0mol/g
・塩素化ポリプロピレン:東洋紡績株式会社製、ハードレンDX526P、塩素含有量26質量%、ニトリル基含有量0mol/g
・クロロプレン・2,3−ジクロルブタジエン共重合物:昭和電工株式会社製、ショウプレンSND8、塩素含有量40質量%、ニトリル基含有量0mol/g
・塩化ビニル・酢酸ビニル共重合物:株式会社カネカ製、カネビニールT555、塩素含有量47質量%、ニトリル基含有量0mol/g
ポリメチルメタクリレート:旭化成ケミカルズ株式会社製、デルペット80N、ハロゲン含有量0質量%、ニトリル基含有量0mol/g
・THF−A:大阪有機化学工業株式会社製、ビスコート#150(テトラヒドロフルフリルアクリレート)
・THF−MA:共栄社化学株式会社製、ライトエステルTHF(テトラヒドロフルフリルメタクリレート)
・MMA:三菱レイヨン株式会社製、アクリエステルM(メチルメタクリレート)
・DMAA:KJケミカルズ株式会社製、DMAA(ジメチルアクリルアミド)
・St:NSスチレンモノマー株式会社製、スチレン
・MA:三菱化学株式会社製、アクリル酸メチル
・TMPTA:大阪有機化学工業株式会社製、ビスコート#295(トリメチロールプロパントリアクリレート)
・DAP100:株式会社大阪ソーダ製、ダイソーダップ100モノマー(ジアリルイソフタレートモノマー)
・Fe(Ac)2:東京化成工業株式会社製、酢酸鉄(II)、分子量:172.19
・TMEDA:広栄化学工業株式会社製、テトラメチルエチレンジアミン、分子量:116.12
・PMDETA:東京化成工業株式会社製、N,N,N',N'',N''−ペンタメチルジエチレントリアミン、分子量:173.3
・Cu(Ac):東京化成工業株式会社製、酢酸銅(I)、分子量:122.59
・TEB−DAP:BASF社製、TEB−DAP(トリエチルボラン−1,3−ジアミノプロパン錯体)、分子量:171.8
・AcOH:東京化成工業株式会社製、酢酸、分子量:60
・GulOH:東京化成工業株式会社製、グルタル酸、分子量:132.12
・BPO:日油株式会社製、ナイパーBW(ベンゾイルペルオキシド、水25質量%含有)、分子量:242.23(なお、表1に記載の値は、水を含むナイパーBWの使用量である。)
・DMany:東京化成工業株式会社製、N,N−ジメチルアニリン、分子量:121.19
・V−70:和光純薬工業株式会社製、油溶性アゾ重合開始剤(2,2'−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル))、分子量:308.43
・BZP:和光純薬工業株式会社製、UVラジカル開始剤(ベンゾフェノン)、分子量:182.22
・KBM−403:信越化学工業株式会社製、3−グリシドキシプロピルトリメトキシシラン
・KBM−5103:信越化学工業株式会社製、3−アクリロキシプロピルトリメトキシシラン
Claims (5)
- 樹脂(A)のハロゲン含有量が30質量%以上である、請求項1に記載の接着剤組成物。
- 前記重合性不飽和基を有する化合物(B)が、(メタ)アクリルモノマーを含む、請求項1〜3のいずれか一項に記載の接着剤組成物。
- 前記重合性不飽和基を有する化合物(B)が、極性基を有する(メタ)アクリルモノマーを含む、請求項1〜4のいずれか一項に記載の接着剤組成物。
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JPS5188532A (ja) * | 1974-03-09 | 1976-08-03 | Setsuchakuzai | |
JPS5991170A (ja) * | 1982-11-18 | 1984-05-25 | Asahi Chem Ind Co Ltd | スラリ−状の高周波接着剤 |
JPS6142583A (ja) * | 1984-08-02 | 1986-03-01 | Asahi Chem Ind Co Ltd | ホツトメルト接着剤 |
JPS6198785A (ja) * | 1984-10-18 | 1986-05-17 | バイヤースドルフ・アクチエンゲゼルシヤフト | 自己接着性テープの製造方法 |
JPH07118350A (ja) * | 1993-10-22 | 1995-05-09 | Sekisui Chem Co Ltd | 光重合性組成物 |
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DE3506242A1 (de) * | 1984-10-18 | 1986-04-24 | Beiersdorf Ag, 2000 Hamburg | Verfahren zur herstellung von selbstklebebaendern |
EP2807224B1 (en) * | 2012-01-23 | 2020-05-13 | Henkel IP & Holding GmbH | Two-part, cyanoacrylate/free radically curable adhesive systems |
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JPS5188532A (ja) * | 1974-03-09 | 1976-08-03 | Setsuchakuzai | |
JPS5991170A (ja) * | 1982-11-18 | 1984-05-25 | Asahi Chem Ind Co Ltd | スラリ−状の高周波接着剤 |
JPS6142583A (ja) * | 1984-08-02 | 1986-03-01 | Asahi Chem Ind Co Ltd | ホツトメルト接着剤 |
JPS6198785A (ja) * | 1984-10-18 | 1986-05-17 | バイヤースドルフ・アクチエンゲゼルシヤフト | 自己接着性テープの製造方法 |
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