JP5556977B1 - 2−シアノアクリレート系接着剤組成物 - Google Patents
2−シアノアクリレート系接着剤組成物 Download PDFInfo
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- JP5556977B1 JP5556977B1 JP2014509960A JP2014509960A JP5556977B1 JP 5556977 B1 JP5556977 B1 JP 5556977B1 JP 2014509960 A JP2014509960 A JP 2014509960A JP 2014509960 A JP2014509960 A JP 2014509960A JP 5556977 B1 JP5556977 B1 JP 5556977B1
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- anion
- adhesive composition
- cyanoacrylate
- cation
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- 239000000203 mixture Substances 0.000 title claims abstract description 69
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000004830 Super Glue Substances 0.000 title claims description 14
- -1 2-cyanoacrylate ester Chemical class 0.000 claims abstract description 83
- 239000000853 adhesive Substances 0.000 claims abstract description 57
- 230000001070 adhesive effect Effects 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 150000001768 cations Chemical class 0.000 claims abstract description 18
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 9
- 229940079826 hydrogen sulfite Drugs 0.000 claims abstract description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 5
- 150000001450 anions Chemical class 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- 238000003860 storage Methods 0.000 abstract description 19
- 229920002725 thermoplastic elastomer Polymers 0.000 abstract description 14
- 229910052751 metal Inorganic materials 0.000 abstract description 12
- 239000002184 metal Substances 0.000 abstract description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- WQGWDDDVZFFDIG-UHFFFAOYSA-N trihydroxybenzene Natural products OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 5
- NXPITPXTYOGNGE-UHFFFAOYSA-M 1-butyl-2,3-dimethylimidazol-3-ium hydrogen sulfate Chemical compound S(=O)(=O)(O)[O-].C(CCC)[N+]1=C(N(C=C1)C)C NXPITPXTYOGNGE-UHFFFAOYSA-M 0.000 description 4
- 229920000858 Cyclodextrin Polymers 0.000 description 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- 229920002943 EPDM rubber Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 4
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000003983 crown ethers Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 4
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229940079877 pyrogallol Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- HDHQZOWEQZQZSO-UHFFFAOYSA-M 1-butyl-3-methylpyridin-1-ium hydron sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+]1=CC=CC(C)=C1 HDHQZOWEQZQZSO-UHFFFAOYSA-M 0.000 description 2
- WACRAFUNNYGNEQ-UHFFFAOYSA-N 1-ethyl-1-methylpiperidin-1-ium Chemical compound CC[N+]1(C)CCCCC1 WACRAFUNNYGNEQ-UHFFFAOYSA-N 0.000 description 2
- OIDIRWZVUWCCCO-UHFFFAOYSA-N 1-ethylpyridin-1-ium Chemical compound CC[N+]1=CC=CC=C1 OIDIRWZVUWCCCO-UHFFFAOYSA-N 0.000 description 2
- UADWUILHKRXHMM-UHFFFAOYSA-N 2-ethylhexyl benzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1 UADWUILHKRXHMM-UHFFFAOYSA-N 0.000 description 2
- 229940106004 2-ethylhexyl benzoate Drugs 0.000 description 2
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 2
- 229920001651 Cyanoacrylate Polymers 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- 244000061458 Solanum melongena Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- UADWUILHKRXHMM-ZDUSSCGKSA-N benzoflex 181 Natural products CCCC[C@H](CC)COC(=O)C1=CC=CC=C1 UADWUILHKRXHMM-ZDUSSCGKSA-N 0.000 description 2
- IUNCEDRRUNZACO-UHFFFAOYSA-N butyl(trimethyl)azanium Chemical compound CCCC[N+](C)(C)C IUNCEDRRUNZACO-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- XTPRURKTXNFVQT-UHFFFAOYSA-N hexyl(trimethyl)azanium Chemical compound CCCCCC[N+](C)(C)C XTPRURKTXNFVQT-UHFFFAOYSA-N 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- ASMNUQAMCVYUSF-UHFFFAOYSA-M methanesulfonate tetraethylphosphanium Chemical compound CS(=O)(=O)[O-].C(C)[P+](CC)(CC)CC ASMNUQAMCVYUSF-UHFFFAOYSA-M 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
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- 239000000758 substrate Substances 0.000 description 2
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- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- HNVRIVKDRYGTED-UHFFFAOYSA-N 1,1-diethylpiperidin-1-ium Chemical compound CC[N+]1(CC)CCCCC1 HNVRIVKDRYGTED-UHFFFAOYSA-N 0.000 description 1
- PWZSCBSKFVJMJH-UHFFFAOYSA-N 1,1-diethylpyrrolidin-1-ium Chemical compound CC[N+]1(CC)CCCC1 PWZSCBSKFVJMJH-UHFFFAOYSA-N 0.000 description 1
- GARJMFRQLMUUDD-UHFFFAOYSA-N 1,1-dimethylpyrrolidin-1-ium Chemical compound C[N+]1(C)CCCC1 GARJMFRQLMUUDD-UHFFFAOYSA-N 0.000 description 1
- DNSADNILRQYBAB-UHFFFAOYSA-N 1,2,3,4-tetramethylimidazol-1-ium Chemical compound CC1=C[N+](C)=C(C)N1C DNSADNILRQYBAB-UHFFFAOYSA-N 0.000 description 1
- KCUGPPHNMASOTE-UHFFFAOYSA-N 1,2,3-trimethylimidazol-1-ium Chemical compound CC=1N(C)C=C[N+]=1C KCUGPPHNMASOTE-UHFFFAOYSA-N 0.000 description 1
- KBNWCDNOTZWFBD-UHFFFAOYSA-N 1,2,4-trimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C(C)=C[N+](C)=C1C KBNWCDNOTZWFBD-UHFFFAOYSA-N 0.000 description 1
- PRSAQEJPKUAHHS-UHFFFAOYSA-N 1,2-diethyl-3-methylimidazol-3-ium Chemical compound CCC=1N(C)C=C[N+]=1CC PRSAQEJPKUAHHS-UHFFFAOYSA-N 0.000 description 1
- IFGGXMRDYJZDJE-UHFFFAOYSA-N 1,2-dimethyl-3-phenylimidazol-1-ium Chemical compound CN1C=C[N+](C=2C=CC=CC=2)=C1C IFGGXMRDYJZDJE-UHFFFAOYSA-N 0.000 description 1
- MXLZUALXSYVAIV-UHFFFAOYSA-N 1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C MXLZUALXSYVAIV-UHFFFAOYSA-N 0.000 description 1
- CDIWYWUGTVLWJM-UHFFFAOYSA-N 1,3,4-trimethylimidazol-1-ium Chemical compound CC1=C[N+](C)=CN1C CDIWYWUGTVLWJM-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- WGBOEVMWOWERBH-UHFFFAOYSA-N 1,3-diethyl-2-methylimidazol-1-ium Chemical compound CCN1C=C[N+](CC)=C1C WGBOEVMWOWERBH-UHFFFAOYSA-N 0.000 description 1
- XLJSMWDFUFADIA-UHFFFAOYSA-N 1,3-diethylimidazol-1-ium Chemical compound CCN1C=C[N+](CC)=C1 XLJSMWDFUFADIA-UHFFFAOYSA-N 0.000 description 1
- NVHSSCNZSOYDCO-UHFFFAOYSA-N 1,3-dimethyl-2-pentylimidazol-1-ium Chemical compound CCCCCC=1N(C)C=C[N+]=1C NVHSSCNZSOYDCO-UHFFFAOYSA-N 0.000 description 1
- OBTFKSNFKVPPFY-UHFFFAOYSA-N 1,3-dimethyl-2-phenylimidazol-1-ium Chemical compound CN1C=C[N+](C)=C1C1=CC=CC=C1 OBTFKSNFKVPPFY-UHFFFAOYSA-N 0.000 description 1
- IJDNIXNJORNVTA-UHFFFAOYSA-N 1,3-dimethyl-2-propylimidazol-1-ium Chemical compound CCCC=1N(C)C=C[N+]=1C IJDNIXNJORNVTA-UHFFFAOYSA-N 0.000 description 1
- WEVAPFAMRHCVDF-UHFFFAOYSA-M 1,3-dimethyl-2-propylimidazol-1-ium hydron sulfate Chemical compound S(=O)(=O)(O)[O-].C[N+]1=C(N(C=C1)C)CCC WEVAPFAMRHCVDF-UHFFFAOYSA-M 0.000 description 1
- DZEHNHDJHLMTNH-UHFFFAOYSA-N 1,3-dimethyl-2-undecylimidazol-1-ium Chemical compound CCCCCCCCCCCC=1N(C)C=C[N+]=1C DZEHNHDJHLMTNH-UHFFFAOYSA-N 0.000 description 1
- DSPUBTKMQXMJCI-UHFFFAOYSA-N 1,3-dimethylbenzimidazol-3-ium Chemical compound C1=CC=C2N(C)C=[N+](C)C2=C1 DSPUBTKMQXMJCI-UHFFFAOYSA-N 0.000 description 1
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 1
- HGIKIBHZIYNEKO-UHFFFAOYSA-N 1-benzyl-2,3-dimethylimidazol-3-ium Chemical compound C1=C[N+](C)=C(C)N1CC1=CC=CC=C1 HGIKIBHZIYNEKO-UHFFFAOYSA-N 0.000 description 1
- COSSPXYCRNRXRX-UHFFFAOYSA-N 1-benzyl-3-methylimidazol-3-ium Chemical compound C1=[N+](C)C=CN1CC1=CC=CC=C1 COSSPXYCRNRXRX-UHFFFAOYSA-N 0.000 description 1
- UVCPHBWNKAXVPC-UHFFFAOYSA-N 1-butyl-1-methylpiperidin-1-ium Chemical compound CCCC[N+]1(C)CCCCC1 UVCPHBWNKAXVPC-UHFFFAOYSA-N 0.000 description 1
- JRSXFDXDHSOEOZ-UHFFFAOYSA-M 1-butyl-1-methylpiperidin-1-ium 4-methylbenzenesulfonate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)[O-])C.C(CCC)[N+]1(CCCCC1)C JRSXFDXDHSOEOZ-UHFFFAOYSA-M 0.000 description 1
- BXLXGYXCAWLXMB-UHFFFAOYSA-M 1-butyl-1-methylpiperidin-1-ium hydron sulfate Chemical compound S(=O)(=O)(O)[O-].C(CCC)[N+]1(CCCCC1)C BXLXGYXCAWLXMB-UHFFFAOYSA-M 0.000 description 1
- UVHSKAXSPUFVDP-UHFFFAOYSA-M 1-butyl-1-methylpiperidin-1-ium methanesulfonate Chemical compound CS(=O)(=O)[O-].C(CCC)[N+]1(CCCCC1)C UVHSKAXSPUFVDP-UHFFFAOYSA-M 0.000 description 1
- PXELHGDYRQLRQO-UHFFFAOYSA-N 1-butyl-1-methylpyrrolidin-1-ium Chemical compound CCCC[N+]1(C)CCCC1 PXELHGDYRQLRQO-UHFFFAOYSA-N 0.000 description 1
- SSVGVFGKUPZBIE-UHFFFAOYSA-M 1-butyl-1-methylpyrrolidin-1-ium 4-methylbenzenesulfonate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)[O-])C.C(CCC)[N+]1(CCCC1)C SSVGVFGKUPZBIE-UHFFFAOYSA-M 0.000 description 1
- YJFNSMFSMIBCLZ-UHFFFAOYSA-M 1-butyl-1-methylpyrrolidin-1-ium hydron sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+]1(C)CCCC1 YJFNSMFSMIBCLZ-UHFFFAOYSA-M 0.000 description 1
- DIGFVIJSOJVYLL-UHFFFAOYSA-M 1-butyl-1-methylpyrrolidin-1-ium;methanesulfonate Chemical compound CS([O-])(=O)=O.CCCC[N+]1(C)CCCC1 DIGFVIJSOJVYLL-UHFFFAOYSA-M 0.000 description 1
- ARGGICXKOZNODB-UHFFFAOYSA-M 1-butyl-2,3-dimethylimidazol-3-ium;4-methylbenzenesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1C.CC1=CC=C(S([O-])(=O)=O)C=C1 ARGGICXKOZNODB-UHFFFAOYSA-M 0.000 description 1
- SEVBIXREHKNSKI-UHFFFAOYSA-M 1-butyl-2,3-dimethylimidazol-3-ium;methanesulfonate Chemical compound CS([O-])(=O)=O.CCCC[N+]=1C=CN(C)C=1C SEVBIXREHKNSKI-UHFFFAOYSA-M 0.000 description 1
- VWFZFKKEKWMXIA-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;4-methylbenzenesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.CC1=CC=C(S([O-])(=O)=O)C=C1 VWFZFKKEKWMXIA-UHFFFAOYSA-M 0.000 description 1
- KXCVJPJCRAEILX-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CCCCN1C=C[N+](C)=C1 KXCVJPJCRAEILX-UHFFFAOYSA-M 0.000 description 1
- PUHVBRXUKOGSBC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;methanesulfonate Chemical compound CS([O-])(=O)=O.CCCC[N+]=1C=CN(C)C=1 PUHVBRXUKOGSBC-UHFFFAOYSA-M 0.000 description 1
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
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- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-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
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 102200082907 rs33918131 Human genes 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- RVKZDIDATLDTNR-UHFFFAOYSA-N sulfanylideneeuropium Chemical compound [Eu]=S RVKZDIDATLDTNR-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- KLIUHARZXKNLFV-UHFFFAOYSA-N tert-butyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)C(C)(C)C KLIUHARZXKNLFV-UHFFFAOYSA-N 0.000 description 1
- SPJZSTLXABSXII-UHFFFAOYSA-N tert-butyl(trimethyl)azanium Chemical compound CC(C)(C)[N+](C)(C)C SPJZSTLXABSXII-UHFFFAOYSA-N 0.000 description 1
- FHELAZMFNUMSEI-UHFFFAOYSA-N tert-butyl-dimethyl-(2-methylpropyl)azanium Chemical compound CC(C)C[N+](C)(C)C(C)(C)C FHELAZMFNUMSEI-UHFFFAOYSA-N 0.000 description 1
- XMPRLBUMOCTEHU-UHFFFAOYSA-N tert-butyl-ethyl-dimethylazanium Chemical compound CC[N+](C)(C)C(C)(C)C XMPRLBUMOCTEHU-UHFFFAOYSA-N 0.000 description 1
- XAMMKFSEEQGBIC-UHFFFAOYSA-N tetra(propan-2-yl)azanium Chemical compound CC(C)[N+](C(C)C)(C(C)C)C(C)C XAMMKFSEEQGBIC-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- CZMILNXHOAKSBR-UHFFFAOYSA-N tetraphenylazanium Chemical compound C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CZMILNXHOAKSBR-UHFFFAOYSA-N 0.000 description 1
- QNUAQGIIURYMJX-UHFFFAOYSA-N tri(propan-2-yl)-propylazanium Chemical compound CCC[N+](C(C)C)(C(C)C)C(C)C QNUAQGIIURYMJX-UHFFFAOYSA-N 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- DLJBCWLKMQZRFN-UHFFFAOYSA-N triethyl(2-methylpropyl)azanium Chemical compound CC[N+](CC)(CC)CC(C)C DLJBCWLKMQZRFN-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- TZWFFXFQARPFJN-UHFFFAOYSA-N triethyl(methyl)phosphanium Chemical compound CC[P+](C)(CC)CC TZWFFXFQARPFJN-UHFFFAOYSA-N 0.000 description 1
- XPLXACTVVUDCNQ-UHFFFAOYSA-N triethyl(propan-2-yl)azanium Chemical compound CC[N+](CC)(CC)C(C)C XPLXACTVVUDCNQ-UHFFFAOYSA-N 0.000 description 1
- WGYXSYLSCVXFDU-UHFFFAOYSA-N triethyl(propyl)azanium Chemical compound CCC[N+](CC)(CC)CC WGYXSYLSCVXFDU-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- WCZKTXKOKMXREO-UHFFFAOYSA-N triethylsulfanium Chemical compound CC[S+](CC)CC WCZKTXKOKMXREO-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- COOSQAXLLKTSQO-UHFFFAOYSA-N trimethyl(2-methylpropyl)azanium Chemical compound CC(C)C[N+](C)(C)C COOSQAXLLKTSQO-UHFFFAOYSA-N 0.000 description 1
- ZVFDPYZBJGKPII-UHFFFAOYSA-N trimethyl(nonyl)azanium Chemical compound CCCCCCCCC[N+](C)(C)C ZVFDPYZBJGKPII-UHFFFAOYSA-N 0.000 description 1
- ACZOGADOAZWANS-UHFFFAOYSA-N trimethyl(pentyl)azanium Chemical compound CCCCC[N+](C)(C)C ACZOGADOAZWANS-UHFFFAOYSA-N 0.000 description 1
- BMTHNVMASXVELE-UHFFFAOYSA-N trimethyl(propan-2-yl)azanium Chemical compound CC(C)[N+](C)(C)C BMTHNVMASXVELE-UHFFFAOYSA-N 0.000 description 1
- QDUATGYYXKDLEI-UHFFFAOYSA-N trimethyl(undecyl)azanium Chemical compound CCCCCCCCCCC[N+](C)(C)C QDUATGYYXKDLEI-UHFFFAOYSA-N 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- OOLZXLYYPCOPQZ-UHFFFAOYSA-N tripropylsulfanium Chemical compound CCC[S+](CCC)CCC OOLZXLYYPCOPQZ-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
2−シアノアクリル酸エステル(a)と、下記一般式(1)で表されるオニウム塩(b)とを含有することを特徴とする2−シアノアクリレート系接着剤組成物。
C+A- (1)
[式中、C+はオニウムカチオンである。A-は硫酸水素アニオン、亜硫酸水素アニオン、R1SO3 -で表されるスルホン酸アニオン(R1はアルキル基、炭素数3〜10のパーフルオロアルキル基、シクロアルキル基、ビニル基、アリール基、パーフルオロアリール基、アラルキル基、もしくはハロゲン原子である)、又は(R2SO2)2N-で表されるビス(置換スルホニル)イミドアニオンである(R2はアルキル基、パーフルオロアルキル基、もしくはアリール基である)。]
Description
また、クラウンエーテル類、またはポリアルキレンオキサイド類を含有する特許文献1〜2に開示される接着剤組成物は、被着体をEPDM、メタクリル樹脂などとした場合、硬化物が白濁する問題があった。カリックスアレン誘導体を含有する特許文献3〜4に開示される接着剤組成物は、被着体を軟質PVCとした場合には同様に硬化物が白濁する問題があった。
1.2−シアノアクリル酸エステル(a)と、下記一般式(1)で表されるオニウム塩(b)とを含有することを特徴とする2−シアノアクリレート系接着剤組成物。
C+A- (1)
[式中、C+はオニウムカチオンである。A-は硫酸水素アニオン、亜硫酸水素アニオン、R1SO3 -で表されるスルホン酸アニオン(R1はアルキル基、炭素数3〜10のパーフルオロアルキル基、シクロアルキル基、ビニル基、アリール基、パーフルオロアリール基、アラルキル基、もしくはハロゲン原子である)、又は(R2SO2)2N-で表されるビス(置換スルホニル)イミドアニオンである(R2はアルキル基、パーフルオロアルキル基、もしくはアリール基である)。]
2.前記オニウム塩(b)のカチオンが、第四級アンモニウムカチオン、イミダゾリウムカチオン、ピリジニウムカチオン、及び第三級スルホニウムカチオンからなる群より選択される少なくとも一つのオニウムカチオンであることを特徴とする前記1に記載の2−シアノアクリレート系接着剤組成物。
3.前記オニウム塩(b)のアニオンが、硫酸水素アニオン及びビス(パーフルオロアルカンスルホニル)イミドアニオンの少なくとも一方であることを特徴とする前記1又は2に記載の2−シアノアクリレート系接着剤組成物。
4.前記オニウム塩(b)のアニオンが、硫酸水素アニオン、亜硫酸水素アニオン、及びR1SO3 -で表されるスルホン酸アニオン(R1はアルキル基、シクロアルキル基、アリール基又はアラルキル基である)。]からなる群より選択される少なくとも一つであることを特徴とする前記1又は2に記載の2−シアノアクリレート系接着剤組成物。
5.前記オニウム塩(b)の含有量が、前記2−シアノアクリル酸エステル(a)100質量部に対して、10〜20000ppmであることを特徴とする前記1〜4のいずれかに記載の2−シアノアクリレート系接着剤組成物。
本発明の接着剤組成物は、2−シアノアクリル酸エステル(a)と、特定の構造を有するオニウム塩(b)とを含有する。
C+A- (1)
[式中、C+はオニウムカチオンである。A-は硫酸水素アニオン、亜硫酸水素アニオン、R1SO3 -で表されるスルホン酸アニオン(R1はアルキル基、炭素数3〜10のパーフルオロアルキル基、シクロアルキル基、ビニル基、アリール基、パーフルオロアリール基、アラルキル基、もしくはハロゲン原子である)、又は(R2SO2)2N-で表されるビス(置換スルホニル)イミドアニオンである(R2はアルキル基、パーフルオロアルキル基、もしくはアリール基である)。]
(1)接着速度
JIS K 6861「α−シアノアクリレート系接着剤の試験方法」に準じて、23℃、60%RH環境下で接着速度を測定した。使用した試験片は次のとおりである。
・アルミニウム:日本テストパネル社製、アルミニウム試験片(材質:A1050P)
・鉄:日本テストパネル社製、鉄試験片(材質S10C)
・スチレン系熱可塑性エラストマー:リケンテクノス社製 商品名「アクティマー A E−2060S」
(2)粘度
E型粘度計を用い、25℃、100rpmの条件下にて測定した。
(3)貯蔵安定性
初期の接着速度及び粘度と、50℃、95%RH環境下で1週間又は2週間保管後の接着速度及び粘度を比較して評価した。保管は、接着剤組成物1.5gを2gポリエチレン容器に密封して行った。
(4)硬化物外観
3mm×25mm×50mmのEPDM(エチレンプロピレンゴム)板、および軟質PVC(ポリ塩化ビニル)板に、接着剤を数滴垂らし、23℃、60%RH環境下で3日間放置し、硬化させた。その硬化物の外観を観察し、評価結果は○×で表した。○は、硬化物に白濁・シワがないことを、×は硬化物に白濁・シワが見られることを示す。使用した試験片は次のとおりである。
・EPDM:中京ゴム社製、EPDM−5065/3t
・軟質PVC:日本ウェーブロック社製、商品名「タフニール Dブルー」
・合成例1(1−ブチル−2,3−ジメチルイミダゾリウム硫酸水素塩)
50mlナス型フラスコに1−ブチル−2,3−ジメチルイミダゾリウムクロリド1.887g(10.00mmol)(表1参照)、陰イオン交換樹脂(オルガノ社製、商品名「アンバーライトIRA900A OH AG」、強塩基型)13.2g(20mg当量)、イオン交換水25mlを仕込み、室温下で48時間攪拌した。イオン交換樹脂をろ別後、氷冷下で49%硫酸水溶液2.002g(10.00mmol)を滴下した。氷浴を外し、室温下で更に12時間攪拌を続けた。これにトルエン25mlを加えて洗浄し、更にイオン交換樹脂で精製後、減圧下で濃縮した。得られた残渣をメタノール25mlに溶解し、不溶物をろ別した。減圧下で溶媒を留去し、淡黄色オイル2.203gを得た。
・合成例2〜4
表1に示した原料と仕込み量に代えた以外は、合成例1と同様にオニウム塩を合成した。
100mlナス型フラスコにジメチルジオクチルアンモニウムブロミド2.103g(3.33mmol)(表1参照)、陰イオン交換樹脂(オルガノ社製、商品名「アンバーライトIRA900A OH AG」、強塩基型)4.40g(6.70mg当量)、メタノール50mlを仕込み、室温下で48時間攪拌した。イオン交換樹脂をろ別後、トルエン15mlに溶媒交換し、溶媒氷冷下で49%硫酸水溶液0.667g(3.33mmol)を滴下した。氷浴を外し、室温下で更に12時間攪拌を続けた。これにイオン交換水10mlを加えて3回洗浄し、無水硫酸マグネシウム上で乾燥させた。減圧下で溶媒を濃縮後、得られた残渣をメタノール25mlに再溶解し、不溶物をろ別した。再度、減圧下で溶媒を留去し、白色固体2.278gを得た。
・実施例1
2−シアノアクリル酸エチルに、二酸化硫黄を20ppm、ハイドロキノンを1000ppm(2−シアノアクリル酸エチルを100質量部とする)配合し、これに1−ブチル−2,3−ジメチルイミダゾリウム硫酸水素塩を100ppm配合して、室温(15〜30℃)で30分間撹拌、混合して接着剤組成物を製造した。得られた接着剤組成物を用いて、アルミニウム及び鉄に対する接着速度、粘度並びに貯蔵安定性を評価した。結果は表2のとおりである。
・実施例2〜13及び比較例1〜5
接着剤組成物に配合するオニウム塩、又は硬化促進剤を表2、3のように代えた以外は、実施例1と同様にして接着剤組成物を製造して評価した。結果は表2、3のとおりである。
・実施例14
2−シアノアクリル酸エチルに、二酸化硫黄を20ppm、ハイドロキノンを1000ppm(2−シアノアクリル酸エチルを100質量部とする)配合し、これに1−ブチル−2,3−ジメチルイミダゾリウム硫酸水素塩を500ppm配合して、室温(15〜30℃)で30分間撹拌、混合して接着剤組成物を製造した。得られた接着剤組成物を用いて、熱可塑性エラストマーに対する接着速度、粘度及び貯蔵安定性を評価した。結果は表4のとおりである。
・実施例15〜22及び比較例6〜8
接着剤組成物に配合するオニウム塩、又は添加剤を表4のように代えた以外は、実施例14と同様にして接着剤組成物を製造して評価した。結果は表4とおりである。
2−シアノアクリル酸エチルに、二酸化硫黄を20ppm、ハイドロキノンを1000ppm(2−シアノアクリル酸エチルを100質量部とする)配合し、これに1−ブチル−3−メチルピリジニウム硫酸水素塩(表1のオニウム塩B)を150ppm配合して、室温(15〜30℃)で30分間撹拌、混合して接着剤組成物を製造した。得られた接着剤組成物を用いて、アルミニウム、鉄及び熱可塑性エラストマーに対する接着速度、および硬化物の外観を評価した。結果は表5のとおりである。
接着剤組成物に配合するオニウム塩、又は硬化促進剤を表5、6のように代えた以外は、実施例23と同様にして接着剤組成物を製造して評価した。結果は表5、6のとおりである。
Claims (5)
- 2−シアノアクリル酸エステル(a)と、下記一般式(1)で表されるオニウム塩(b)とを含有することを特徴とする2−シアノアクリレート系接着剤組成物。
C+A- (1)
[式中、C+はオニウムカチオンである。A-は硫酸水素アニオン、亜硫酸水素アニオン、R1SO3 -で表されるスルホン酸アニオン(R1はアルキル基、炭素数3〜10のパーフルオロアルキル基、シクロアルキル基、ビニル基、アリール基、パーフルオロアリール基、アラルキル基、もしくはハロゲン原子である)、又は(R2SO2)2N-で表されるビス(置換スルホニル)イミドアニオンである(R2はアルキル基、パーフルオロアルキル基、もしくはアリール基である)。] - 前記オニウム塩(b)のカチオンが、第四級アンモニウムカチオン、イミダゾリウムカチオン、ピリジニウムカチオン、及び第三級スルホニウムカチオンからなる群より選択される少なくとも一つのオニウムカチオンであることを特徴とする請求項1に記載の2−シアノアクリレート系接着剤組成物。
- 前記オニウム塩(b)のアニオンが、硫酸水素アニオン及びビス(パーフルオロアルカンスルホニル)イミドアニオンの少なくとも一方であることを特徴とする請求項1又は2に記載の2−シアノアクリレート系接着剤組成物。
- 前記オニウム塩(b)のアニオンが、硫酸水素アニオン、亜硫酸水素アニオン、及びR1SO3 -で表されるスルホン酸アニオン(R1はアルキル基、シクロアルキル基、アリール基又はアラルキル基である)。]からなる群より選択される少なくとも一つであることを特徴とする請求項1又は2に記載の2−シアノアクリレート系接着剤組成物。
- 前記オニウム塩(b)の含有量が、前記2−シアノアクリル酸エステル(a)100質量部に対して、10〜20000ppmであることを特徴とする請求項1〜4のいずれか1項に記載の2−シアノアクリレート系接着剤組成物。
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Publication number | Priority date | Publication date | Assignee | Title |
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Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US9688840B2 (en) | 2014-03-11 | 2017-06-27 | Toagosei Co., Ltd. | 2-cyanoacrylate adhesive composition |
WO2015137156A1 (ja) * | 2014-03-12 | 2015-09-17 | 東亞合成株式会社 | 2-シアノアクリレート系接着剤組成物 |
JP6319897B2 (ja) * | 2014-05-27 | 2018-05-09 | 田岡化学工業株式会社 | 2−シアノアクリレート系接着剤用プライマー |
TWI664224B (zh) * | 2014-12-12 | 2019-07-01 | 日商東亞合成股份有限公司 | Two-liquid type hardening composition |
JP6571481B2 (ja) * | 2015-10-14 | 2019-09-04 | ピアス株式会社 | 2−シアノアクリレートモノマーの重合促進剤、及び、体毛に繊維を接着させる方法 |
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Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53129231A (en) * | 1977-04-19 | 1978-11-11 | Toagosei Chem Ind Co Ltd | Adhesion composition |
EP0080269A1 (en) * | 1981-11-20 | 1983-06-01 | Minnesota Mining And Manufacturing Company | Novel adhesive compositions and bonding method employing the same |
JPS60179482A (ja) * | 1984-01-27 | 1985-09-13 | ロクタイト.(アイルランド).リミテッド | 瞬間接着剤組成物 |
JPS62100567A (ja) * | 1985-10-26 | 1987-05-11 | Toagosei Chem Ind Co Ltd | 硬化性組成物 |
JPS63128088A (ja) * | 1986-11-17 | 1988-05-31 | Koatsu Gas Kogyo Kk | α−シアノアクリレ−ト接着剤組成物 |
JPH02115287A (ja) * | 1988-10-25 | 1990-04-27 | Aron Kasei Co Ltd | 接着剤組成物および接着方法 |
GB2228943A (en) * | 1989-03-06 | 1990-09-12 | Loctite | Cyanoacrylate compositions for bonding porous or non-active substrates |
WO1998007801A1 (en) * | 1996-08-16 | 1998-02-26 | Loctite (Ireland) Limited | Cyanoacrylate compositions with improved thermal and glass bonding performance |
WO1998018876A1 (de) * | 1996-10-25 | 1998-05-07 | Henkel Kommanditgesellschaft Auf Aktien | Fluoreszierender cyanacrylatklebstoff |
JP2000044891A (ja) * | 1998-07-29 | 2000-02-15 | Koatsu Gas Kogyo Co Ltd | 瞬間接着剤組成物 |
JP2000073014A (ja) * | 1998-09-01 | 2000-03-07 | Toagosei Co Ltd | 2−シアノアクリレート系組成物 |
WO2001085861A1 (en) * | 2000-05-12 | 2001-11-15 | Loctite (R & D) Limited | Activator compositions for cyanoacrylate adhesives |
WO2010014641A2 (en) * | 2008-07-31 | 2010-02-04 | Closure Medical Corporation | Controlled exotherm of cyanoacrylate formulations |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2228943A (en) | 1939-06-16 | 1941-01-14 | Bergstein Samuel | Egg carton assembling device |
US4108747A (en) | 1976-07-14 | 1978-08-22 | General Electric Company | Curable compositions and method for curing such compositions |
JPS6037836B2 (ja) | 1977-08-05 | 1985-08-28 | 東亞合成株式会社 | 接着剤組成物 |
AT365623B (de) | 1980-03-10 | 1982-02-10 | Teroson Gmbh | Cyanoacrylat-klebstoffzusammensetzung |
JPS588771A (ja) | 1981-07-08 | 1983-01-18 | Taoka Chem Co Ltd | 接着剤組成物 |
EP0142327B1 (en) | 1983-11-10 | 1987-05-13 | Loctite Corporation | Instant adhesive composition |
US4695615A (en) | 1984-11-21 | 1987-09-22 | Loctite (Ireland) Limited | Instant adhesive composition utilizing mixed functionality calixarenes as accelerators |
US4980086A (en) * | 1985-10-16 | 1990-12-25 | Toagosei Chemical Industry, Co., Ltd. | Curable composition |
EP0259016B1 (en) | 1986-08-29 | 1990-07-04 | LOCTITE (IRELAND) Ltd. | Calixarene derivatives and use of such compounds as accelerators in instant adhesive compositions |
JP2671528B2 (ja) | 1989-11-27 | 1997-10-29 | 東亞合成株式会社 | 瞬間接着剤組成物 |
DE4009621A1 (de) | 1990-03-26 | 1991-10-02 | Henkel Kgaa | (alpha) -cyanacrylatklebstoffzusammensetzungen |
JP4374685B2 (ja) * | 1998-11-17 | 2009-12-02 | 東レ株式会社 | ポリエステル樹脂組成物 |
JP2000191600A (ja) | 1998-12-28 | 2000-07-11 | Toagosei Co Ltd | 環状化合物、該環状化合物からなる2―シアノアクリレ―ト用硬化促進剤、並びに2―シアノアクリレ―ト系組成物 |
US20080003196A1 (en) * | 2006-06-30 | 2008-01-03 | Jonn Jerry Y | Absorbable cyanoacrylate compositions |
JP2011202161A (ja) * | 2010-03-02 | 2011-10-13 | Nitto Denko Corp | 粘着剤組成物、粘着シート、及び、表面保護フィルム |
CN101812278A (zh) * | 2010-05-20 | 2010-08-25 | 上海西怡新材料科技有限公司 | 紫外固化有机硅-丙烯酸树脂电子胶及其应用 |
JP5723618B2 (ja) * | 2011-02-04 | 2015-05-27 | 日東電工株式会社 | 粘着シートおよび表面保護フィルム |
-
2013
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- 2013-09-06 WO PCT/JP2013/074035 patent/WO2014042082A1/ja active Application Filing
- 2013-09-06 KR KR1020157006202A patent/KR102039370B1/ko active IP Right Grant
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53129231A (en) * | 1977-04-19 | 1978-11-11 | Toagosei Chem Ind Co Ltd | Adhesion composition |
EP0080269A1 (en) * | 1981-11-20 | 1983-06-01 | Minnesota Mining And Manufacturing Company | Novel adhesive compositions and bonding method employing the same |
JPS60179482A (ja) * | 1984-01-27 | 1985-09-13 | ロクタイト.(アイルランド).リミテッド | 瞬間接着剤組成物 |
JPS62100567A (ja) * | 1985-10-26 | 1987-05-11 | Toagosei Chem Ind Co Ltd | 硬化性組成物 |
JPS63128088A (ja) * | 1986-11-17 | 1988-05-31 | Koatsu Gas Kogyo Kk | α−シアノアクリレ−ト接着剤組成物 |
JPH02115287A (ja) * | 1988-10-25 | 1990-04-27 | Aron Kasei Co Ltd | 接着剤組成物および接着方法 |
GB2228943A (en) * | 1989-03-06 | 1990-09-12 | Loctite | Cyanoacrylate compositions for bonding porous or non-active substrates |
WO1998007801A1 (en) * | 1996-08-16 | 1998-02-26 | Loctite (Ireland) Limited | Cyanoacrylate compositions with improved thermal and glass bonding performance |
WO1998018876A1 (de) * | 1996-10-25 | 1998-05-07 | Henkel Kommanditgesellschaft Auf Aktien | Fluoreszierender cyanacrylatklebstoff |
JP2000044891A (ja) * | 1998-07-29 | 2000-02-15 | Koatsu Gas Kogyo Co Ltd | 瞬間接着剤組成物 |
JP2000073014A (ja) * | 1998-09-01 | 2000-03-07 | Toagosei Co Ltd | 2−シアノアクリレート系組成物 |
WO2001085861A1 (en) * | 2000-05-12 | 2001-11-15 | Loctite (R & D) Limited | Activator compositions for cyanoacrylate adhesives |
WO2010014641A2 (en) * | 2008-07-31 | 2010-02-04 | Closure Medical Corporation | Controlled exotherm of cyanoacrylate formulations |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014141645A (ja) * | 2012-12-26 | 2014-08-07 | Toagosei Co Ltd | 2−シアノアクリレート系接着剤組成物 |
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