JPH024604B2 - - Google Patents
Info
- Publication number
- JPH024604B2 JPH024604B2 JP60149266A JP14926685A JPH024604B2 JP H024604 B2 JPH024604 B2 JP H024604B2 JP 60149266 A JP60149266 A JP 60149266A JP 14926685 A JP14926685 A JP 14926685A JP H024604 B2 JPH024604 B2 JP H024604B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- maleimide
- acrylate
- fumarate
- parts
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 28
- 239000000853 adhesive Substances 0.000 claims description 23
- 230000001070 adhesive effect Effects 0.000 claims description 23
- -1 fumaric acid diester Chemical class 0.000 claims description 22
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 12
- 239000001530 fumaric acid Substances 0.000 claims description 10
- 239000007870 radical polymerization initiator Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 35
- MKVYSRNJLWTVIK-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O MKVYSRNJLWTVIK-UHFFFAOYSA-N 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- FNMTVMWFISHPEV-AATRIKPKSA-N dipropan-2-yl (e)-but-2-enedioate Chemical compound CC(C)OC(=O)\C=C\C(=O)OC(C)C FNMTVMWFISHPEV-AATRIKPKSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- 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 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KPQOXMCRYWDRSB-UHFFFAOYSA-N 1-(2-chlorophenyl)pyrrole-2,5-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C=CC1=O KPQOXMCRYWDRSB-UHFFFAOYSA-N 0.000 description 2
- KEVMYFLMMDUPJE-UHFFFAOYSA-N 2,7-dimethyloctane Chemical group CC(C)CCCCC(C)C KEVMYFLMMDUPJE-UHFFFAOYSA-N 0.000 description 2
- LUYISICIYVKBTA-UHFFFAOYSA-N 6-methylquinoline Chemical compound N1=CC=CC2=CC(C)=CC=C21 LUYISICIYVKBTA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 238000009863 impact test Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 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
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- ONEIBTGSNPDDSB-UHFFFAOYSA-N 1-(2,4,6-tribromophenyl)pyrrole-2,5-dione Chemical compound BrC1=CC(Br)=CC(Br)=C1N1C(=O)C=CC1=O ONEIBTGSNPDDSB-UHFFFAOYSA-N 0.000 description 1
- VHZJMAJCUAWIHV-UHFFFAOYSA-N 1-(2,4,6-trichlorophenyl)pyrrole-2,5-dione Chemical compound ClC1=CC(Cl)=CC(Cl)=C1N1C(=O)C=CC1=O VHZJMAJCUAWIHV-UHFFFAOYSA-N 0.000 description 1
- LJPKFNSTOUAVHM-UHFFFAOYSA-N 1-(2,4-dinitrophenyl)pyrrole-2,5-dione Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1N1C(=O)C=CC1=O LJPKFNSTOUAVHM-UHFFFAOYSA-N 0.000 description 1
- VMDQUQBEIFMAIC-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC(C)=C1N1C(=O)C=CC1=O VMDQUQBEIFMAIC-UHFFFAOYSA-N 0.000 description 1
- JXAXVKYMRFXDGB-UHFFFAOYSA-N 1-(2-chloro-4-phenoxyphenyl)pyrrole-2,5-dione Chemical compound ClC1=C(C=CC(=C1)OC1=CC=CC=C1)N1C(C=CC1=O)=O JXAXVKYMRFXDGB-UHFFFAOYSA-N 0.000 description 1
- CNDOSNMFHUSKGN-UHFFFAOYSA-N 1-(2-hydroxyphenyl)pyrrole-2,5-dione Chemical compound OC1=CC=CC=C1N1C(=O)C=CC1=O CNDOSNMFHUSKGN-UHFFFAOYSA-N 0.000 description 1
- LJDGDRYFCIHDPX-UHFFFAOYSA-N 1-(2-methoxyphenyl)pyrrole-2,5-dione Chemical compound COC1=CC=CC=C1N1C(=O)C=CC1=O LJDGDRYFCIHDPX-UHFFFAOYSA-N 0.000 description 1
- QYOJZFBQEAZNEW-UHFFFAOYSA-N 1-(2-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC=C1N1C(=O)C=CC1=O QYOJZFBQEAZNEW-UHFFFAOYSA-N 0.000 description 1
- NBIYKOUEZOEMMC-UHFFFAOYSA-N 1-(2-methylpropyl)pyrrole-2,5-dione Chemical compound CC(C)CN1C(=O)C=CC1=O NBIYKOUEZOEMMC-UHFFFAOYSA-N 0.000 description 1
- SCXAYTWCHGRQPA-UHFFFAOYSA-N 1-(2-nitrophenyl)pyrrole-2,5-dione Chemical compound [O-][N+](=O)C1=CC=CC=C1N1C(=O)C=CC1=O SCXAYTWCHGRQPA-UHFFFAOYSA-N 0.000 description 1
- KOHAAQZNKXPOID-UHFFFAOYSA-N 1-(2-tert-butylphenyl)pyrrole-2,5-dione Chemical compound CC(C)(C)C1=CC=CC=C1N1C(=O)C=CC1=O KOHAAQZNKXPOID-UHFFFAOYSA-N 0.000 description 1
- QDEQBRUNBFJJPW-UHFFFAOYSA-N 1-(3-chlorophenyl)pyrrole-2,5-dione Chemical compound ClC1=CC=CC(N2C(C=CC2=O)=O)=C1 QDEQBRUNBFJJPW-UHFFFAOYSA-N 0.000 description 1
- YWODHBPFOGXUFX-UHFFFAOYSA-N 1-(3-hydroxyphenyl)pyrrole-2,5-dione Chemical compound OC1=CC=CC(N2C(C=CC2=O)=O)=C1 YWODHBPFOGXUFX-UHFFFAOYSA-N 0.000 description 1
- UNCUTNPWBZKJHD-UHFFFAOYSA-N 1-(3-methoxyphenyl)pyrrole-2,5-dione Chemical compound COC1=CC=CC(N2C(C=CC2=O)=O)=C1 UNCUTNPWBZKJHD-UHFFFAOYSA-N 0.000 description 1
- PRZFFHNZHXGTRC-UHFFFAOYSA-N 1-(3-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC(N2C(C=CC2=O)=O)=C1 PRZFFHNZHXGTRC-UHFFFAOYSA-N 0.000 description 1
- CJENYVWFVWQVPS-UHFFFAOYSA-N 1-(3-nitrophenyl)pyrrole-2,5-dione Chemical compound [O-][N+](=O)C1=CC=CC(N2C(C=CC2=O)=O)=C1 CJENYVWFVWQVPS-UHFFFAOYSA-N 0.000 description 1
- WMVQPXZRECDSMJ-UHFFFAOYSA-N 1-(3-tert-butylphenyl)pyrrole-2,5-dione Chemical compound C(C)(C)(C)C=1C=C(C=CC1)N1C(C=CC1=O)=O WMVQPXZRECDSMJ-UHFFFAOYSA-N 0.000 description 1
- MDBNEJWCBWGPAH-UHFFFAOYSA-N 1-(4-benzylphenyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=CC=C1 MDBNEJWCBWGPAH-UHFFFAOYSA-N 0.000 description 1
- FECSFBYOMHWJQG-UHFFFAOYSA-N 1-(4-bromophenyl)pyrrole-2,5-dione Chemical compound C1=CC(Br)=CC=C1N1C(=O)C=CC1=O FECSFBYOMHWJQG-UHFFFAOYSA-N 0.000 description 1
- SBAWYTBRPFRLCO-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenyl)pyrrole-2,5-dione Chemical compound COC1=C(C=CC(=C1)Cl)N1C(C=CC1=O)=O SBAWYTBRPFRLCO-UHFFFAOYSA-N 0.000 description 1
- FPZQYYXSOJSITC-UHFFFAOYSA-N 1-(4-chlorophenyl)pyrrole-2,5-dione Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C=CC1=O FPZQYYXSOJSITC-UHFFFAOYSA-N 0.000 description 1
- HLQZPKWGAFLVHJ-UHFFFAOYSA-N 1-(4-ethoxyphenyl)pyrrole-2,5-dione Chemical compound C1=CC(OCC)=CC=C1N1C(=O)C=CC1=O HLQZPKWGAFLVHJ-UHFFFAOYSA-N 0.000 description 1
- BLLFPKZTBLMEFG-UHFFFAOYSA-N 1-(4-hydroxyphenyl)pyrrole-2,5-dione Chemical compound C1=CC(O)=CC=C1N1C(=O)C=CC1=O BLLFPKZTBLMEFG-UHFFFAOYSA-N 0.000 description 1
- XAHCEMQKWSQGLQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)pyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C=CC1=O XAHCEMQKWSQGLQ-UHFFFAOYSA-N 0.000 description 1
- KCFXNGDHQPMIAQ-UHFFFAOYSA-N 1-(4-methylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)C=CC1=O KCFXNGDHQPMIAQ-UHFFFAOYSA-N 0.000 description 1
- CVKDEEISKBRPEQ-UHFFFAOYSA-N 1-(4-nitrophenyl)pyrrole-2,5-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)C=CC1=O CVKDEEISKBRPEQ-UHFFFAOYSA-N 0.000 description 1
- VAYJAEOCYWSGBB-UHFFFAOYSA-N 1-(4-phenoxyphenyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1OC1=CC=CC=C1 VAYJAEOCYWSGBB-UHFFFAOYSA-N 0.000 description 1
- ZRZQZANNUGOTIE-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1OCC1=CC=CC=C1 ZRZQZANNUGOTIE-UHFFFAOYSA-N 0.000 description 1
- RXWKCYQPTDVVSI-UHFFFAOYSA-N 1-(4-phenylphenyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(C=2C=CC=CC=2)C=C1 RXWKCYQPTDVVSI-UHFFFAOYSA-N 0.000 description 1
- QLDJXEMIAHBMSS-UHFFFAOYSA-N 1-(4-tert-butylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C=CC1=O QLDJXEMIAHBMSS-UHFFFAOYSA-N 0.000 description 1
- LRKQOBVRDZQHMR-UHFFFAOYSA-N 1-[4-(phenoxymethyl)phenyl]pyrrole-2,5-dione Chemical compound O(C1=CC=CC=C1)CC1=CC=C(C=C1)N1C(C=CC1=O)=O LRKQOBVRDZQHMR-UHFFFAOYSA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 1
- BAWHYOHVWHQWFQ-UHFFFAOYSA-N 1-naphthalen-1-ylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC2=CC=CC=C12 BAWHYOHVWHQWFQ-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- NQDOCLXQTQYUDH-UHFFFAOYSA-N 1-propan-2-ylpyrrole-2,5-dione Chemical compound CC(C)N1C(=O)C=CC1=O NQDOCLXQTQYUDH-UHFFFAOYSA-N 0.000 description 1
- DABFKTHTXOELJF-UHFFFAOYSA-N 1-propylpyrrole-2,5-dione Chemical compound CCCN1C(=O)C=CC1=O DABFKTHTXOELJF-UHFFFAOYSA-N 0.000 description 1
- YEKDUBMGZZTUDY-UHFFFAOYSA-N 1-tert-butylpyrrole-2,5-dione Chemical compound CC(C)(C)N1C(=O)C=CC1=O YEKDUBMGZZTUDY-UHFFFAOYSA-N 0.000 description 1
- AENZGWONVTXLRC-UHFFFAOYSA-N 2-(2,5-dioxopyrrol-1-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1C(=O)C=CC1=O AENZGWONVTXLRC-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- 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
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- UJTRCPVECIHPBG-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C2CCCCC2)=C1 UJTRCPVECIHPBG-UHFFFAOYSA-N 0.000 description 1
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 1
- LKUOJDGRNKVVFF-UHFFFAOYSA-N 4-(2,5-dioxopyrrol-1-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(=O)C=CC1=O LKUOJDGRNKVVFF-UHFFFAOYSA-N 0.000 description 1
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical compound C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- YUASDDSPOMCHPW-UHFFFAOYSA-N N=[S+]CC1=CC=CC=C1 Chemical compound N=[S+]CC1=CC=CC=C1 YUASDDSPOMCHPW-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 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
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-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
- 230000005856 abnormality Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- ROPXFXOUUANXRR-BUHFOSPRSA-N bis(2-ethylhexyl) (e)-but-2-enedioate Chemical compound CCCCC(CC)COC(=O)\C=C\C(=O)OCC(CC)CCCC ROPXFXOUUANXRR-BUHFOSPRSA-N 0.000 description 1
- RSRICHZMFPHXLE-AATRIKPKSA-N bis(2-methylpropyl) (e)-but-2-enedioate Chemical compound CC(C)COC(=O)\C=C\C(=O)OCC(C)C RSRICHZMFPHXLE-AATRIKPKSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 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
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- CPZVJYPXOWWFSW-VAWYXSNFSA-N dibenzyl (e)-but-2-enedioate Chemical compound C=1C=CC=CC=1COC(=O)/C=C/C(=O)OCC1=CC=CC=C1 CPZVJYPXOWWFSW-VAWYXSNFSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- BLKQQTCUGZJWLN-VAWYXSNFSA-N dicyclohexyl (e)-but-2-enedioate Chemical compound C1CCCCC1OC(=O)/C=C/C(=O)OC1CCCCC1 BLKQQTCUGZJWLN-VAWYXSNFSA-N 0.000 description 1
- BVVRPLNLVUMGSL-FMQUCBEESA-N didecyl (e)-but-2-enedioate Chemical compound CCCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCCC BVVRPLNLVUMGSL-FMQUCBEESA-N 0.000 description 1
- HEJZJSIRBLOWPD-WCWDXBQESA-N didodecyl (e)-but-2-enedioate Chemical compound CCCCCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCCCCC HEJZJSIRBLOWPD-WCWDXBQESA-N 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- KUUZQLFCCOGXKQ-BUHFOSPRSA-N diheptyl (e)-but-2-enedioate Chemical compound CCCCCCCOC(=O)\C=C\C(=O)OCCCCCCC KUUZQLFCCOGXKQ-BUHFOSPRSA-N 0.000 description 1
- QMCVOSQFZZCSLN-VAWYXSNFSA-N dihexyl (e)-but-2-enedioate Chemical compound CCCCCCOC(=O)\C=C\C(=O)OCCCCCC QMCVOSQFZZCSLN-VAWYXSNFSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- PQJYOOFQDXGDDS-ISLYRVAYSA-N dinonyl (e)-but-2-enedioate Chemical compound CCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCC PQJYOOFQDXGDDS-ISLYRVAYSA-N 0.000 description 1
- TVWTZAGVNBPXHU-FOCLMDBBSA-N dioctyl (e)-but-2-enedioate Chemical compound CCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCC TVWTZAGVNBPXHU-FOCLMDBBSA-N 0.000 description 1
- NFCMRHDORQSGIS-MDZDMXLPSA-N dipentyl (e)-but-2-enedioate Chemical compound CCCCCOC(=O)\C=C\C(=O)OCCCCC NFCMRHDORQSGIS-MDZDMXLPSA-N 0.000 description 1
- DSTWFRCNXMNXTR-AATRIKPKSA-N dipropyl (e)-but-2-enedioate Chemical compound CCCOC(=O)\C=C\C(=O)OCCC DSTWFRCNXMNXTR-AATRIKPKSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-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
- IACADKPZFMDWGT-UHFFFAOYSA-N ethene;propane-1,2,3-triol Chemical compound C=C.C=C.C=C.C=C.OCC(O)CO.OCC(O)CO IACADKPZFMDWGT-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229930004008 p-menthane Natural products 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical group CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は使用時の作業性が良好であるように粘
度を適度に低く調整することが容易で、硬化性に
優れると同時に硬化物の耐熱性、可撓性に優れた
嫌気性接着剤組成物に関するものである。
（従来の技術）
嫌気性接着剤組成物は、通常空気又は酸素と接
触した状態では液状を保持して硬化しないが、空
気又は酸素から遮断されれば急速に重合硬化する
性質を有しているので、種々の密封剤、例えばボ
ルト・ナツトのネジ部の固定、ベアリングシヤフ
トの固定など広く実用化されている。しかし、近
年のエレクトロニクス産業の発展に伴ない、より
高度な要求、例えば速硬化性への改良、耐熱性の
向上、より多くの種類の基材への適応性などが要
求され、更には高品質、生産性向上の要求に対し
て、嫌気硬化性のみならず紫外線硬化性をも付与
された紫外線硬化型の嫌気性接着剤への期待も大
きい。
従来よりこれらの諸要求に対していくつかの努
力がなされて来ている。例えば少量の水を含有す
ることができる親水性の嫌気重合性単量体と限定
された触媒系と水との組合せにより速硬化とする
方法（特開昭59−207977号）、スルホン結合を分
子内に有するジ（メタ）アクリレートを利用して
耐熱性を高める方法（特開昭54−150491号）、ジ
（メタ）アクリレートオリゴマーとフエニルマレ
イミド或いはビスマレイミドとの組合せにより熱
特性を改良する方法（特公昭59−13555号）、ヒド
ロキシエチルアクリレート、エチルアクリレート
等のアクリレート類を希釈剤として加え組成物の
粘度を低くして、使用時の作業性を向上さす方法
などがある。しかし、これらの方法は、速硬化性
にはなるものの耐水性、耐熱性が充分でない場
合、また、耐熱性の向上は見られるが速硬化性が
充分でなかつたり、組成物の粘度が高すぎて使い
にくくなる場合、粘度が低く作業性が良くなる反
面耐熱性が不充分となる場合など、いずれも問題
を残しているのが現状である。
（発明が解決しようとする問題点）
本発明者らは上記問題点を解決するため鋭意研
究の結果、（メタ）アクリルオリゴマーと遊離基
重合開始剤にフマル酸のジエステル及びマレイミ
ド化合物を組合せて嫌気性接着剤として用いたと
ころ、作業性が良好となるように粘度を適度に低
く調整することが容易で、速硬化性であり、硬化
物の耐熱性や可撓性にも優れていることを見出し
て、本発明を完成させた。
（問題点を解決するための手段および作用）
即ち本発明は、一分子中に１個以上の（メタ）
アクリロイル基を有する（メタ）アクリルオリゴ
マー(A)、フマル酸ジエステル(B)、
一般式
（但し、式中R1およびR2はそれぞれ独立に水
素、ハロゲン、炭素数１〜15のアルキル基、アリ
ール基又は置換アリール基であり、R3は水素、
炭素数１〜15のアルキル基、シクロアルキル基、
アリール基又は置換アリール基である。）
で表わされるマレイミド化合物(C)及び遊離基重合
開始剤(A)を含んでなる嫌気性接着剤組成物に関す
るものである。
本発明で使用される（メタ）アクリルオリゴマ
ー(A)は、一分子中に（メタ）アクリロイル基を１
個以上含有するものがすべて包含されるが、一分
子中に（メタ）アクリロイル基を２個含有するジ
（メタ）アクリレートオリゴマーが主となる様な
組合せで用いるのが一般的である。これら（メ
タ）アクリルオリゴマーの組合せは使用目的に応
じて最適のものを選択すればよい。（メタ）アク
リルオリゴマー(A)を例示すれば、例えばエチレン
グリコールジ（メタ）アクリレート、ジエチレン
グリコールジ（メタ）アクリレート、プロピレン
グリコールジ（メタ）アクリレート、トリエチレ
ングリコールジ（メタ）アクリレート、テトラエ
チレングリコールジ（メタ）アクリレート、ジプ
ロピレングリコールジ（メタ）アクリレート、ジ
ペンタメチレングリコールジ（メタ）アクリレー
ト、テトラエチレンジグリセロールテトラ（メ
タ）アクリレート、テトラメチレンジ（メタ）ア
クリレート、ネオペンチルグリコールジ（メタ）
アクリレート、１，３−ブタンジオールジ（メ
タ）アクリレート、トリメチロールプロパントリ
（メタ）アクリレート、トリメチロールエタント
リ（メタ）アクリレート、ペンタエリスリトール
テトラ（メタ）アクリレート、ジペンタエリスリ
トールヘキサ（メタ）アクリレート、ビスフエノ
ールＡアルキレンオキサイド付加物のジ（メタ）
アクリレート、ハロゲン化ビスフエノールＡアル
キレンオキサイド付加物のジ（メタ）アクリレー
ト、ビスフエノールＳアルキレンオキサイド付加
物のジ（メタ）アクリレート、グリセリンジ（メ
タ）アクリレートのような多価アルコールのポリ
（メタ）アクリレート類、ポリエステルポリ（メ
タ）アクリレート類、ウレタンポリ（メタ）アク
リレート類、エポキシポリ（メタ）アクリレート
類、メチル（メタ）アクリレート、ヒドロキシエ
チル（メタ）アクリレート、ヒドロキシプロピル
（メタ）アクリレート、グリシジル（メタ）アク
リレート、シクロヘキシル（メタ）アクリレー
ト、フエノキシエチル（メタ）アクリレート、ラ
ウリル（メタ）アクリレート、ジフエニル（メ
タ）アクリロイルオキシエチルフオスフエート、
ジブチル（メタ）アクリロイルオキシエチルフオ
スフエート、ジシクロペンテニル（メタ）アクリ
レート、ジシクロペンテニルオキシエチル（メ
タ）アクリレート、イソボルニル（メタ）アクリ
レート、トリス（メタ）アクリロイルオキシエチ
ルフオスフエート、トリス（メタ）アクリロイル
オキシエチルイソシアヌレート、トリ（メタ）ア
クリロイルヘキサヒドロ−ｓ−トリアジン等を挙
げることが出来る。
本発明で使用されるフマル酸ジエステル(B)はフ
マル酸と炭素数１〜20を有するアルキル基、シク
ロアルキル基、アリール基又は置換アリール基を
有するアルコール類とのジエステルであり、アル
コール類としては同一であつても、異つていても
よい。これらのフマル酸ジエステルは例えばフマ
ル酸ジメチル、フマル酸ジエチル、フマル酸ジプ
ロピル、フマル酸ジイソプロピル、フマル酸ジブ
チル、フマル酸ジイソブチル、フマル酸ジsec.ブ
チル、フマル酸ジｔ−ブチル、フマル酸ジアミ
ル、フマル酸ジイソアミル、フマル酸ジヘキシ
ル、フマル酸ジヘプチル、フマル酸ジオクチル、
フマル酸ジ・２−エチルヘキシル、フマル酸ジノ
ニル、フマル酸ジデシル、フマル酸ジラウリル、
フマル酸ジシクロヘキシル、フマル酸ジベンジル
等を挙げることが出来る。
嫌気性接着剤組成物で使用する（メタ）アクリ
ルオリゴマーの種類によつては高粘度となり、作
業性に問題を生ずることが多いが、本発明で用い
るフマル酸ジエステル(B)は（メタ）アクリルオリ
ゴマー(A)やマレイミド化合物(C)に対して可塑剤と
しての効果を有し、組成物を適度な粘度に調整す
ることが容易となる上に、従来の粘度低下剤にお
ける耐熱性低下傾向は全く見られず、むしろ耐熱
性を向上したり可撓性を付与する効果を発揮す
る。
本発明で使用されるマレイミド化合物(C)は、前
記一般式で表わされるものであり、中でもR3が
アリール基又は置換アリール基が好ましい。マレ
イミド化合物(C)は得られる組成物の耐熱性の向上
に大きく寄与するものであり、更には速硬化性と
くに紫外線照射を併用する硬化システムでは一段
と速硬化性を付与するので、生産性向上につなが
るものである。マレイミド化合物(C)は大半が常温
で固体であるので、（メタ）アクリルオリゴマー
(A)への溶解性に制限が生じたり、組成物の粘性が
高くなる場合もあるが、前記した如くフマル酸ジ
エステル(B)はこのような問題にも好ましい効果を
もたらす。
マレイミド化合物(C)の使用に当つては、使用目
的に応じて１種又は２種以上を有効に使用するこ
とが出来る。これらのマレイミド化合物(C)として
は、例えばマレイミド、Ｎ−メチルマレイミド、
Ｎ−エチルマレイミド、Ｎ−プロピルマレイミ
ド、Ｎ−イソプロピルマレイミド、Ｎ−ブチルマ
レイミド、Ｎ−イソブチルマレイミド、Ｎ−ター
シヤリブチルマレイミド、Ｎ−シクロヘキシルマ
レイミド、Ｎ−ラウリルマレイミド、Ｎ−フエニ
ルマレイミド、Ｎ−（２−クロルフエニル）マレ
イミド、Ｎ−（３−クロルフエニル）マレイミド、
Ｎ−（４−クロルフエニル）マレイミド、Ｎ−（４
−ブロモフエニル）マレイミド、Ｎ−（２，４，
６−トリクロルフエニル）マレイミド、Ｎ−（２，
４，６−トリブロモフエニル）マレイミド、Ｎ−
（２−メチルフエニル）マレイミド、Ｎ−（３−メ
チルフエニル）マレイミド、Ｎ−（４−メチルフ
エニル）マレイミド、Ｎ−（２−ターシヤリブチ
ルフエニル）マレイミド、Ｎ−（３−ターシヤリ
ブチルフエニル）マレイミド、Ｎ−（４−ターシ
ヤリブチルフエニル）マレイミド、Ｎ−（２，６
−ジメチルフエニル）マレイミド、Ｎ−（２−ニ
トロフエニル）マレイミド、Ｎ−（３−ニトロフ
エニル）マレイミド、Ｎ−（４−ニトロフエニル）
マレイミド、Ｎ−（２，４−ジニトロフエニル）
マレイミド、Ｎ−（２−ヒドロキシフエニル）マ
レイミド、Ｎ−（３−ヒドロキシフエニル）マレ
イミド、Ｎ−（４−ヒドロキシフエニル）マレイ
ミド、Ｎ−（２−メトキシフエニル）マレイミド、
Ｎ−（３−メトキシフエニル）マレイミド、Ｎ−
（４−メトキシフエニル）マレイミド、Ｎ−（４−
エトキシフエニル）マレイミド、Ｎ−（２−メト
キシ−４−クロルフエニル）マレイミド、Ｎ−
（４−フエニルフエニル）マレイミド、Ｎ−（４−
フエニロキシフエニル）マレイミド、Ｎ−（４−
ベンジルフエニル）マレイミド、Ｎ−（４−ベン
ジロキシフエニル）マレイミド、Ｎ−（４−フエ
ノキシメチルフエニル）マレイミド、Ｎ−（２−
クロル−４−フエノキシフエニル）マレイミド、
Ｎ−ナフチルマレイミド、Ｎ−（２−カルボキシ
フエニル）マレイミド、Ｎ−（４−カルボキシフ
エニル）マレイミド等が挙げられる。
遊離基重合開始剤(D)としては、ハイドロパーオ
キサイド類、ケトンパーオキサイド類、ジアルキ
ルパーオキサイド類、パーオキシエステル類等の
公知の遊離基重合開始剤を使用することが出来
る。例えば過酸化ベンゾイル、ｐ−クロル過酸化
ベンゾイル、ジクミルパーオキサイド、ジ−ｔ−
ブチルパーオキサイド、ｔ−ブチルパーオキシベ
ンゾエート、ｔ−ブチルパーオキシ−イソプロピ
ルカーボネート、メチルエチルケトンパーオキサ
イド、シクロヘキサノンパーオキサイド、キユメ
ンハイドロパーオキサイド、ｔ−ブチルハイドロ
パーオキサイド、ジイソプロピルベンゼンハイド
ロパーオキサイド、ｐ−メンタンハイドロパーオ
キサイド等が挙げられる。
本発明の嫌気性接着剤組成物の主たる構成成分
である（メタ）アクリルオリゴマー(A)、フマル酸
ジエステル(B)、マレイミド化合物(C)及び遊離基重
合開始剤(D)の配合割合は、使用目的に応じて配合
されるもので特定はされないが、通常の配合割合
は、（メタ）アクリルオリゴマー(A)100重量部に対
して、フマル酸ジエステル(B)１〜50重量部、マレ
イミド化合物(C)0.1〜50重量部の範囲の割合であ
り、また、遊離基重合開始剤(D)は（メタ）アクリ
ルオリゴマー(A)とフマル酸ジエステル(B)とマレイ
ミド化合物(C)との合計量に対して0.01〜５重量％
の割合で使用される。この範囲をはずれた割合で
配合すると、前記した如き諸性能に優れた嫌気性
接着剤組成物が得られないことがある。
本発明の組成物には嫌気重合を促進する目的で
使用される公知の促進剤、例えばベンズスルフイ
ミドや第２級もしくは第３級有機アミン類を適宜
併用することが可能である。また、フエノール系
やキノン系重合禁止剤、シユウ酸やエチレンジア
ミン・４酢酸塩等公知の安定剤、シランカツプリ
ング剤、チタンカツプリング剤、着色剤、増粘
剤、チクソトロピツク剤及び可塑剤等も適量添加
することも可能である。
更に、紫外線硬化を応用する際には公知の光重
合開始剤、例えばベンゾイン、ベンジル、ベンゾ
インアルキルエーテル、ベンゾフエノン、アセト
フエノン等を有効に使用すればよい。
（発明の効果）
本発明の嫌気性接着剤組成物は、作業性が良好
となるように粘度を適度に低く調整することが容
易で、速硬化性であり、硬化物の耐熱性や可撓性
にも優れているので、ボルト・ナツトのネジ部の
固定をはじめとし、電気・電子部品の接着、自動
車部品の接着など、紫外線などの光硬化併用も含
めて、広い分野で応用が可能である。
更に、本発明の嫌気性接着剤組成物は、硬化物
の可撓性にも優れているので、衝撃力が加わるよ
うな短時間硬化接着の場合、例えばモーターケー
スとフエライトの接着において、割れ、はがれ等
の問題が生じることがない。
次に実施例を挙げて本発明を更に詳しく説明す
るが、本発明は実施例により制限を受けるもので
はない。なお、例中の部は重量部、％は重量％を
表わすものとする。なお、各接着剤の性能試験は
以下の方法で行つた。
(1) 接着開始時間
M10のボルトのネジすじの上に接着剤組成物を
塗布し、ナツトをねじ込んで締めつけトルクを加
えないで固定した後、23℃で放置し、接着の開始
によつてナツトが手で動かなくなるまでの時間を
測定した。
(2) 破壊トルク強度
接着開始時間測定試験と同様の方法で接着剤組
成物を塗布して固定したボルト・ナツトを23℃で
24時間放置した後、トルクレンチを用いて戻し、
最初に動き始めた時のトルク強度を測定し、破壊
トルク強度とした。
(3) 脱出トルク強度
破壊トルク強度の測定後1/4、1/2、3/4および
４／４回転のトルク強度を同様に測定し、それらの
平均値を求めて脱出トルク強度とした。
(4) 耐熱強度
脱出トルク強度試験と同様に固定養生したル
ト・ナツトを180℃で６時間加熱し、しかる後加
熱状態で脱出トルク強度を同じ方法で求めて耐熱
強度とした。
(5) 作業性
接着剤組成物の調製時、使用時を含めた取り扱
い易さを○、△、×の３段階表示した。
(6) 衝撃試験
0.5mm厚の鋼板の片面に嫌気性接着剤組成物を
塗布したのち、25μ厚のポリエステルフイルムを
塗布面に圧着して窒素雰囲気中で硬化接着させた
試験板を、デポン式衝撃試験（１Kg荷重−50cm）
により衝撃を与え、接着剤膜の状態を観察する。
○：異常なし
△：わずかにクラツクがる状態
×：クラツク、割れ発生
参考例 １
撹拌機、滴下ロート付きのガラス製フラスコに
テトラハイドロ無水フタル酸152部、メタクリル
酸86部及びトリエチルアミン2.4部を仕込んで、
内温を80℃に昇温した。次いで、プロピオンオキ
サイド128部を滴下ロートより５時間にわたつて
滴下し、酸価が１以下になる迄同温度に保持した
後、未反応プロピレンオキサイドを70℃、60mmＨ
ｇの条件で留去した。
得られた反応生成物100部に対しジブチル錫ジ
ラウレート0.1部を加え、内温を40℃に保持しな
がら、空気雰囲気下で２，４−トリレンジイソシ
アネート23部を１時間にわたつて滴下した。滴下
終了後、内温を60℃に昇温して同温度に３時間保
持して反応を終了させ、25℃における粘度が約
1500ポイズのウレタンジメタクリレート(1)を得
た。
実施例 １
下記配合により本発明の嫌気性接着剤組成物を
調製して性能試験を行つた。
ウレタンジメタクリレート(1) 65部
Ｎ−（ｏ−クロルフエニル）マレイミド25部
フマル酸ジイソプロピル 10部
クメンハイドロパーオキサイド １部
ｏ−ベンズスルフイミド 0.5部
Ｎ，Ｎ−ジメチルアニリン 0.5部
試験結果を第１表に示す。
比較例 １
実施例１においてフマル酸ジイソプロピルを使
用せずウレタンジメタクリレート(1)を75部とする
他は、実施例１と同様の操作で比較用の嫌気性接
着剤組成物を調製して性能試験を行つた。試験結
果を第１表に示す。
比較例 ２
実施例１においてフマル酸ジイソプロピルをア
クリル酸イソプロピルに置換える他は、実施例１
と同様の操作で比較用の嫌気性接着剤組成物を調
製して性能試験を行つた。試験結果を第１表に示
す。
実施例 ２
下記配合により本発明の嫌気性接着剤組成物を
調製して性能試験を行つた。
ウレタンジメタクリレート(1) 70部
エチルマレイミド 25部
フマル酸ジブチル ５部
クメンハイドロパーオキサイド １部
ｏ−ベンズスルフイミド 0.5部
６−メチルキノリン 0.5部
シユウ酸 0.005部
試験結果を第１表に示す。
実施例 ３
下記配合により本発明の嫌気性接着剤組成物を
調製して性能試験を行つた。
ビスフエノールＡエチレンオキサイド３モル付
加物のジメタクリレート 67部
シクロヘキシルマレイミド 25部
フマル酸ジイソプロピル ８部
クメンハイドロパーオキサイド １部
ｏ−ベンズスルフイミド 0.5部
Ｎ，Ｎ−ジメチルアニリン 0.5部
試験結果を第１表に示す。
【表】Detailed Description of the Invention (Industrial Field of Application) The present invention allows easy adjustment of the viscosity to an appropriately low level for good workability during use. The present invention relates to an anaerobic adhesive composition with excellent properties and flexibility. (Prior Art) Anaerobic adhesive compositions normally remain liquid and do not harden when in contact with air or oxygen, but they have the property of rapidly polymerizing and hardening when cut off from air or oxygen. Therefore, various sealants have been widely put into practical use, for example, for fixing threaded parts of bolts and nuts, and for fixing bearing shafts. However, with the development of the electronics industry in recent years, more advanced requirements such as improved fast curing, improved heat resistance, and adaptability to more types of base materials are required, and even higher quality In order to meet the demand for improved productivity, there are high expectations for UV-curable anaerobic adhesives that have not only anaerobic curability but also UV curability. Several efforts have been made in the past to meet these requirements. For example, a method for rapid curing by combining a hydrophilic anaerobically polymerizable monomer that can contain a small amount of water, a limited catalyst system, and water (Japanese Patent Application Laid-open No. 59-207977), A method of improving heat resistance by using di(meth)acrylate contained in the product (Japanese Patent Application Laid-Open No. 150491/1989), and a method of improving thermal properties by combining di(meth)acrylate oligomer with phenylmaleimide or bismaleimide. (Japanese Patent Publication No. 59-13555), there is a method in which acrylates such as hydroxyethyl acrylate and ethyl acrylate are added as a diluent to lower the viscosity of the composition and improve workability during use. However, these methods can be used in cases where the water resistance and heat resistance are insufficient even though the composition is fast curing, or when the fast curing property is not sufficient although the heat resistance is improved, or the viscosity of the composition is too high. At present, problems still remain in both cases, such as when the viscosity is low and the workability is good, but the heat resistance is insufficient. (Problems to be Solved by the Invention) In order to solve the above-mentioned problems, the present inventors have conducted intensive research and found that a (meth)acrylic oligomer and a free radical polymerization initiator are combined with a diester of fumaric acid and a maleimide compound. When used as a adhesive, it was found that the viscosity could be easily adjusted to a moderately low level for good workability, that it cured quickly, and that the cured product had excellent heat resistance and flexibility. They discovered this and completed the present invention. (Means and effects for solving the problem) That is, the present invention provides one or more (meta) molecules in one molecule.
(Meth)acrylic oligomer with acryloyl group (A), fumaric acid diester (B), general formula (However, in the formula, R 1 and R 2 are each independently hydrogen, halogen, an alkyl group having 1 to 15 carbon atoms, an aryl group, or a substituted aryl group, and R 3 is hydrogen,
Alkyl group having 1 to 15 carbon atoms, cycloalkyl group,
It is an aryl group or a substituted aryl group. ) The present invention relates to an anaerobic adhesive composition comprising a maleimide compound (C) represented by the following formula and a free radical polymerization initiator (A). The (meth)acrylic oligomer (A) used in the present invention has one (meth)acryloyl group in one molecule.
Although any combination containing 2 or more (meth)acryloyl groups is included, it is common to use a combination in which a di(meth)acrylate oligomer containing two (meth)acryloyl groups in one molecule is the main one. The optimal combination of these (meth)acrylic oligomers may be selected depending on the purpose of use. Examples of (meth)acrylic oligomers (A) include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, and tetraethylene glycol di(meth)acrylate. (meth)acrylate, dipropylene glycol di(meth)acrylate, dipentamethylene glycol di(meth)acrylate, tetraethylene diglycerol tetra(meth)acrylate, tetramethylene di(meth)acrylate, neopentyl glycol di(meth)acrylate
Acrylate, 1,3-butanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bis Di(meth) of phenol A alkylene oxide adduct
Acrylate, di(meth)acrylate of halogenated bisphenol A alkylene oxide adduct, di(meth)acrylate of bisphenol S alkylene oxide adduct, poly(meth)acrylate of polyhydric alcohol such as glycerine di(meth)acrylate , polyester poly(meth)acrylates, urethane poly(meth)acrylates, epoxy poly(meth)acrylates, methyl(meth)acrylate, hydroxyethyl(meth)acrylate, hydroxypropyl(meth)acrylate, glycidyl(meth)acrylate Acrylate, cyclohexyl (meth)acrylate, phenoxyethyl (meth)acrylate, lauryl (meth)acrylate, diphenyl (meth)acryloyloxyethyl phosphate,
Dibutyl (meth)acryloyloxyethyl phosphate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, tris(meth)acryloyloxyethyl phosphate, tris(meth) Examples include acryloyloxyethyl isocyanurate, tri(meth)acryloylhexahydro-s-triazine, and the like. The fumaric acid diester (B) used in the present invention is a diester of fumaric acid and an alcohol having an alkyl group, a cycloalkyl group, an aryl group, or a substituted aryl group having 1 to 20 carbon atoms. They may be the same or different. These diesters of fumarate include, for example, dimethyl fumarate, diethyl fumarate, dipropyl fumarate, diisopropyl fumarate, dibutyl fumarate, diisobutyl fumarate, disec.butyl fumarate, dit-butyl fumarate, diamyl fumarate, fumarate. diisoamyl acid, dihexyl fumarate, diheptyl fumarate, dioctyl fumarate,
Di-2-ethylhexyl fumarate, dinonyl fumarate, didecyl fumarate, dilauryl fumarate,
Examples include dicyclohexyl fumarate and dibenzyl fumarate. Depending on the type of (meth)acrylic oligomer used in the anaerobic adhesive composition, the viscosity may be high, which often causes problems in workability, but the fumaric acid diester (B) used in the present invention is a (meth)acrylic oligomer. It has a plasticizing effect on oligomers (A) and maleimide compounds (C), making it easy to adjust the composition to an appropriate viscosity, and reducing the tendency for heat resistance to decrease in conventional viscosity-lowering agents. It is not visible at all, but rather has the effect of improving heat resistance and imparting flexibility. The maleimide compound (C) used in the present invention is represented by the above general formula, and R 3 is preferably an aryl group or a substituted aryl group. The maleimide compound (C) greatly contributes to improving the heat resistance of the resulting composition, and it also provides fast curing properties, especially in curing systems that use ultraviolet irradiation, which improves productivity. It is something that connects. Most maleimide compounds (C) are solid at room temperature, so (meth)acrylic oligomers
Although the solubility in (A) may be limited or the viscosity of the composition may increase, as described above, fumaric acid diester (B) has a favorable effect on such problems. When using the maleimide compound (C), one type or two or more types can be effectively used depending on the purpose of use. Examples of these maleimide compounds (C) include maleimide, N-methylmaleimide,
N-ethylmaleimide, N-propylmaleimide, N-isopropylmaleimide, N-butylmaleimide, N-isobutylmaleimide, N-tertiarybutylmaleimide, N-cyclohexylmaleimide, N-laurylmaleimide, N-phenylmaleimide, N- (2-chlorophenyl)maleimide, N-(3-chlorophenyl)maleimide,
N-(4-chlorophenyl)maleimide, N-(4
-bromophenyl)maleimide, N-(2,4,
6-trichlorophenyl)maleimide, N-(2,
4,6-tribromophenyl)maleimide, N-
(2-methylphenyl)maleimide, N-(3-methylphenyl)maleimide, N-(4-methylphenyl)maleimide, N-(2-tertiarybutylphenyl)maleimide, N-(3-tertiarybutylphenyl)maleimide , N-(4-tertiarybutylphenyl)maleimide, N-(2,6
-dimethylphenyl)maleimide, N-(2-nitrophenyl)maleimide, N-(3-nitrophenyl)maleimide, N-(4-nitrophenyl)
Maleimide, N-(2,4-dinitrophenyl)
maleimide, N-(2-hydroxyphenyl)maleimide, N-(3-hydroxyphenyl)maleimide, N-(4-hydroxyphenyl)maleimide, N-(2-methoxyphenyl)maleimide,
N-(3-methoxyphenyl)maleimide, N-
(4-methoxyphenyl)maleimide, N-(4-
ethoxyphenyl)maleimide, N-(2-methoxy-4-chlorophenyl)maleimide, N-
(4-Phenylphenyl)maleimide, N-(4-
phenyloxyphenyl)maleimide, N-(4-
benzylphenyl)maleimide, N-(4-benzyloxyphenyl)maleimide, N-(4-phenoxymethylphenyl)maleimide, N-(2-
chloro-4-phenoxyphenyl)maleimide,
Examples include N-naphthylmaleimide, N-(2-carboxyphenyl)maleimide, N-(4-carboxyphenyl)maleimide, and the like. As the free radical polymerization initiator (D), known free radical polymerization initiators such as hydroperoxides, ketone peroxides, dialkyl peroxides, peroxy esters, etc. can be used. For example, benzoyl peroxide, p-chlorobenzoyl peroxide, dicumyl peroxide, di-t-
Butyl peroxide, t-butyl peroxybenzoate, t-butyl peroxy-isopropyl carbonate, methyl ethyl ketone peroxide, cyclohexanone peroxide, kyumene hydroperoxide, t-butyl hydroperoxide, diisopropylbenzene hydroperoxide, p-menthane Examples include hydroperoxide. The blending ratios of the (meth)acrylic oligomer (A), fumaric acid diester (B), maleimide compound (C), and free radical polymerization initiator (D), which are the main components of the anaerobic adhesive composition of the present invention, are as follows: Although it is not specified and is blended depending on the purpose of use, the usual blending ratio is 1 to 50 parts by weight of fumaric acid diester (B) and maleimide compound to 100 parts by weight of (meth)acrylic oligomer (A). (C) in a proportion ranging from 0.1 to 50 parts by weight, and the free radical polymerization initiator (D) is the sum of the (meth)acrylic oligomer (A), the fumaric acid diester (B), and the maleimide compound (C). 0.01-5% by weight based on the amount
used at a rate of If blended in a ratio outside this range, an anaerobic adhesive composition with excellent performance as described above may not be obtained. Known accelerators used for the purpose of accelerating anaerobic polymerization, such as benzyl sulfimide and secondary or tertiary organic amines, may be appropriately used in the composition of the present invention. In addition, appropriate amounts of phenolic and quinone polymerization inhibitors, known stabilizers such as oxalic acid and ethylenediamine/tetraacetate, silane coupling agents, titanium coupling agents, colorants, thickeners, thixotropic agents, and plasticizers, etc. It is also possible to add. Furthermore, when applying ultraviolet curing, known photopolymerization initiators such as benzoin, benzyl, benzoin alkyl ether, benzophenone, acetophenone, etc. may be effectively used. (Effects of the Invention) The anaerobic adhesive composition of the present invention has a viscosity that can be easily adjusted to an appropriately low level for good workability, is fast curing, and has excellent heat resistance and flexibility when cured. Because it has excellent properties, it can be applied in a wide range of fields, including fixing threaded parts of bolts and nuts, adhesion of electrical and electronic parts, and adhesion of automobile parts, including the use of light curing such as ultraviolet rays. be. Furthermore, the anaerobic adhesive composition of the present invention has excellent flexibility in the cured product, so in the case of short-curing adhesives where impact force is applied, for example, when bonding a motor case and ferrite, cracks, cracks, No problems such as peeling occur. Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited by the Examples. In addition, parts in the examples are parts by weight, and % is weight %. Note that performance tests for each adhesive were conducted in the following manner. (1) Adhesion start time After applying the adhesive composition onto the thread of an M10 bolt, screwing in the nut and fixing it without applying any tightening torque, leave it at 23°C, and the nut will start to tighten by the start of adhesion. The time it took for the robot to stop moving by hand was measured. (2) Breaking torque strength Bolts and nuts fixed by applying an adhesive composition in the same manner as the adhesion start time measurement test were heated at 23°C.
After leaving it for 24 hours, use a torque wrench to return it.
The torque strength when it first started moving was measured and was defined as the breaking torque strength. (3) Escape torque strength After measuring the breaking torque strength, the torque strengths of 1/4, 1/2, 3/4, and 4/4 rotations were similarly measured, and the average value thereof was determined as the escape torque strength. (4) Heat Resistance Strength Similar to the breakout torque strength test, fixed and cured nuts were heated at 180°C for 6 hours, and then the breakout torque strength was determined in the same manner in the heated state to determine the heat resistance strength. (5) Workability The ease of handling the adhesive composition, including during preparation and use, was expressed in three grades: ○, △, and ×. (6) Impact test After applying an anaerobic adhesive composition to one side of a 0.5 mm thick steel plate, a 25 μ thick polyester film was pressed onto the coated surface and cured in a nitrogen atmosphere. Impact test (1Kg load - 50cm)
Apply a shock to the adhesive and observe the condition of the adhesive film. ○: No abnormality △: Slight cracking ×: Cracking, reference example of cracking 1. 152 parts of tetrahydrophthalic anhydride, 86 parts of methacrylic acid, and 2.4 parts of triethylamine were placed in a glass flask equipped with a stirrer and a dropping funnel. in,
The internal temperature was raised to 80°C. Next, 128 parts of propion oxide was added dropwise from the dropping funnel over 5 hours and the temperature was maintained until the acid value became 1 or less.
It was distilled off under the conditions of g. 0.1 part of dibutyltin dilaurate was added to 100 parts of the obtained reaction product, and 23 parts of 2,4-tolylene diisocyanate was added dropwise over 1 hour under an air atmosphere while maintaining the internal temperature at 40°C. After the dropwise addition, the internal temperature was raised to 60°C and maintained at the same temperature for 3 hours to complete the reaction, and the viscosity at 25°C was approximately
Urethane dimethacrylate (1) of 1500 poise was obtained. Example 1 An anaerobic adhesive composition of the present invention was prepared using the following formulation and a performance test was conducted. Urethane dimethacrylate (1) 65 parts N-(o-chlorophenyl)maleimide 25 parts Diisopropyl fumarate 10 parts Cumene hydroperoxide 1 part o-benzsulfimide 0.5 part N,N-dimethylaniline 0.5 parts Shown in the table. Comparative Example 1 A comparative anaerobic adhesive composition was prepared in the same manner as in Example 1, except that diisopropyl fumarate was not used and urethane dimethacrylate (1) was changed to 75 parts. I conducted a test. The test results are shown in Table 1. Comparative Example 2 Example 1 except that diisopropyl fumarate in Example 1 was replaced with isopropyl acrylate.
A comparative anaerobic adhesive composition was prepared in the same manner as above, and a performance test was conducted. The test results are shown in Table 1. Example 2 An anaerobic adhesive composition of the present invention was prepared using the following formulation and a performance test was conducted. Urethane dimethacrylate (1) 70 parts Ethylmaleimide 25 parts Dibutyl fumarate 5 parts Cumene hydroperoxide 1 part o-benzsulfimide 0.5 part 6-methylquinoline 0.5 part Oxalic acid 0.005 part The test results are shown in Table 1. Example 3 An anaerobic adhesive composition of the present invention was prepared according to the following formulation and a performance test was conducted. Dimethacrylate of 3 moles of bisphenol A ethylene oxide adduct 67 parts Cyclohexylmaleimide 25 parts Diisopropyl fumarate 8 parts Cumene hydroperoxide 1 part o-benzsulfimide 0.5 part N,N-dimethylaniline 0.5 part Shown in the table. 【table】
Claims (1)
基を有する（メタ）アクリルオリゴマー(A)、 フマル酸ジエステル(B)、 一般式 （但し、式中R1およびR2はそれぞれ独立に水
素、ハロゲン、炭素数１〜15のアルキル基、アリ
ール基又は置換アリール基であり、R3は水素、
炭素数１〜15のアルキル基、シクロアルキル基、
アリール基又は置換アリール基である。） で表わされるマレイミド化合物(C)及び遊離基重合
開始剤(D) を含んでなる嫌気性接着剤組成物。[Claims] 1 (meth)acrylic oligomer (A) having one or more (meth)acryloyl groups in one molecule, fumaric acid diester (B), general formula (However, in the formula, R 1 and R 2 are each independently hydrogen, halogen, an alkyl group having 1 to 15 carbon atoms, an aryl group, or a substituted aryl group, and R 3 is hydrogen,
Alkyl group having 1 to 15 carbon atoms, cycloalkyl group,
It is an aryl group or a substituted aryl group. ) An anaerobic adhesive composition comprising a maleimide compound (C) represented by (C) and a free radical polymerization initiator (D).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14926685A JPS6210179A (en) | 1985-07-09 | 1985-07-09 | Anaerobic adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14926685A JPS6210179A (en) | 1985-07-09 | 1985-07-09 | Anaerobic adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6210179A JPS6210179A (en) | 1987-01-19 |
| JPH024604B2 true JPH024604B2 (en) | 1990-01-29 |
Family
ID=15471481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14926685A Granted JPS6210179A (en) | 1985-07-09 | 1985-07-09 | Anaerobic adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6210179A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09183950A (en) * | 1995-12-28 | 1997-07-15 | Koatsu Gas Kogyo Co Ltd | Two-pack acrylic adhesive composition |
| ATE333114T1 (en) | 1998-01-30 | 2006-08-15 | Albemarle Corp | PHOTOPOLYMERIZABLE COMPOSITIONS CONTAINING MALEIMIDE AND METHODS OF USE THEREOF |
| WO2000077108A1 (en) * | 1999-06-10 | 2000-12-21 | Korea Research Institute Of Chemical Technology | Anaerobic adhesive composition |
| WO2005049755A1 (en) * | 2003-11-24 | 2005-06-02 | Samsung Electronics Co., Ltd | Uv-hardenable adhesive composition, optical reading head using said composition and optical recording/reproducing device comprising said reading head |
| CN100383210C (en) * | 2005-12-14 | 2008-04-23 | 黑龙江省石油化学研究院 | Low temperature detachable anaerobic adhesive and method for preparing the same |
| CN100463924C (en) * | 2006-03-20 | 2009-02-25 | 广州市坚红化工厂 | Anaerobic oxygen rubber initiating agent and anaerobic oxygen rubber having same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51112895A (en) * | 1975-03-12 | 1976-10-05 | Loctite Corp | Curable composition |
| JPS51125185A (en) * | 1974-10-10 | 1976-11-01 | Loctite Corp | Heattresistant curable composition |
-
1985
- 1985-07-09 JP JP14926685A patent/JPS6210179A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51125185A (en) * | 1974-10-10 | 1976-11-01 | Loctite Corp | Heattresistant curable composition |
| JPS51112895A (en) * | 1975-03-12 | 1976-10-05 | Loctite Corp | Curable composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6210179A (en) | 1987-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100995257B1 (en) | Curable composition and method for temporal fixation of structural member using the same | |
| JP5151419B2 (en) | Photocurable composition for producing photocurable adhesive and photocurable adhesive sheet | |
| JP2642554B2 (en) | Adhesive composition | |
| US6596787B1 (en) | Non-yellowing fast cure speed UV\visible curable liquid acrylic ester adhesives for glass bonding | |
| KR0133554B1 (en) | Adhesive composition | |
| US11912801B2 (en) | (Meth)acrylate urethane (urea) phosphonates as adhesion promoters | |
| JPH024604B2 (en) | ||
| JP4306918B2 (en) | Flame retardant resin composition, flame retardant adhesive composition, and metal joined body | |
| JP4311852B2 (en) | Flame retardant resin composition, flame retardant adhesive composition, and metal joined body | |
| TW201922906A (en) | Cure accelerators for anaerobic curable compositions | |
| JP2769747B2 (en) | Adhesive composition | |
| CN109072029B (en) | Radical-curable adhesive composition and adhesive | |
| JPH0621134B2 (en) | Photocurable resin composition | |
| JP3345785B2 (en) | Acrylic heat-resistant adhesive composition | |
| JP2003313206A (en) | Anaerobic curable composition | |
| JPH04345677A (en) | Adhesive composition | |
| JPH06206942A (en) | Curable resin composition | |
| JPS62265318A (en) | Anaerobically curable composition | |
| JPS61293277A (en) | Anaerobic adhesive composition | |
| JPS61291667A (en) | Anaerobic adhesive composition | |
| JPH0987590A (en) | Adhesive composition | |
| JP2001262107A (en) | Flame-retardant resin composition, flame-retardant adhesive composition and metal-joined article | |
| JPH032465B2 (en) | ||
| JP2000355647A (en) | Curable resin composition and adhesive composition | |
| JPH09183950A (en) | Two-pack acrylic adhesive composition |