JPWO2014091966A1 - 接着剤組成物 - Google Patents
接着剤組成物 Download PDFInfo
- Publication number
- JPWO2014091966A1 JPWO2014091966A1 JP2014551991A JP2014551991A JPWO2014091966A1 JP WO2014091966 A1 JPWO2014091966 A1 JP WO2014091966A1 JP 2014551991 A JP2014551991 A JP 2014551991A JP 2014551991 A JP2014551991 A JP 2014551991A JP WO2014091966 A1 JPWO2014091966 A1 JP WO2014091966A1
- Authority
- JP
- Japan
- Prior art keywords
- polyol
- adhesive composition
- cyanoacrylate
- cyano
- molecular weight
- 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.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 112
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 109
- 239000000203 mixture Substances 0.000 title claims abstract description 82
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 150000001768 cations Chemical class 0.000 claims abstract description 14
- 150000001450 anions Chemical class 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 13
- -1 2-cyanoacrylic acid ester Chemical class 0.000 claims description 148
- 229920005862 polyol Polymers 0.000 claims description 54
- 229920001577 copolymer Polymers 0.000 claims description 51
- 150000003077 polyols Chemical class 0.000 claims description 50
- 239000000178 monomer Substances 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 30
- 239000002245 particle Substances 0.000 claims description 22
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 15
- 230000008859 change Effects 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000005062 Polybutadiene Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229920002857 polybutadiene Polymers 0.000 claims description 10
- 229920001195 polyisoprene Polymers 0.000 claims description 10
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229920000515 polycarbonate Polymers 0.000 claims description 7
- 239000004417 polycarbonate Substances 0.000 claims description 7
- 229920005906 polyester polyol Polymers 0.000 claims description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229940079826 hydrogen sulfite Drugs 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
- 239000005011 phenolic resin Substances 0.000 claims description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- OCOCSIDEWXUOQN-UHFFFAOYSA-N 2-cyanopenta-2,4-dienoic acid Chemical compound OC(=O)C(C#N)=CC=C OCOCSIDEWXUOQN-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
- 239000012071 phase Substances 0.000 description 41
- 238000012360 testing method Methods 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
- 239000000377 silicon dioxide Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 10
- 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 9
- 229920001651 Cyanoacrylate Polymers 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 239000000806 elastomer Substances 0.000 description 8
- 229910021485 fumed silica Inorganic materials 0.000 description 8
- 230000002209 hydrophobic effect Effects 0.000 description 8
- 229920001451 polypropylene glycol Polymers 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 229910002012 Aerosil® Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 5
- WQGWDDDVZFFDIG-UHFFFAOYSA-N trihydroxybenzene Natural products OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- 229920000858 Cyclodextrin Polymers 0.000 description 4
- JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical compound CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-UHFFFAOYSA-N 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 238000007664 blowing Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229940078672 didecyldimethylammonium Drugs 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- QRWOVIRDHQJFDB-UHFFFAOYSA-N isobutyl cyanoacrylate Chemical compound CC(C)COC(=O)C(=C)C#N QRWOVIRDHQJFDB-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 4
- 230000035939 shock Effects 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
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 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
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- WYNCDLDEWVNKJX-UHFFFAOYSA-M methyl(trioctyl)azanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC WYNCDLDEWVNKJX-UHFFFAOYSA-M 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229940079877 pyrogallol Drugs 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 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
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- IQDPHMACOQAPBQ-UHFFFAOYSA-N 2-ethoxyethyl 2-cyanoprop-2-enoate Chemical compound CCOCCOC(=O)C(=C)C#N IQDPHMACOQAPBQ-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
- CQVWXNBVRLKXPE-UHFFFAOYSA-N 2-octyl cyanoacrylate Chemical compound CCCCCCC(C)OC(=O)C(=C)C#N CQVWXNBVRLKXPE-UHFFFAOYSA-N 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
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- KVBQQRZTJLIBFL-UHFFFAOYSA-N [C-]1(C=CC=C1)C[N+](C)(C)CCCCCCCCCCCC.[CH-]1C=CC=C1.[Fe+2] Chemical compound [C-]1(C=CC=C1)C[N+](C)(C)CCCCCCCCCCCC.[CH-]1C=CC=C1.[Fe+2] KVBQQRZTJLIBFL-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 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
- QSRFYFHZPSGRQX-UHFFFAOYSA-N benzyl(tributyl)azanium Chemical compound CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 QSRFYFHZPSGRQX-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-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
- 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 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- 150000003983 crown ethers Chemical class 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 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
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- 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
- 238000009826 distribution Methods 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- XTPRURKTXNFVQT-UHFFFAOYSA-N hexyl(trimethyl)azanium Chemical compound CCCCCC[N+](C)(C)C XTPRURKTXNFVQT-UHFFFAOYSA-N 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
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- MRCJOMGYXUMDTI-UHFFFAOYSA-M hydron triethyl(methyl)phosphanium sulfate Chemical compound S(=O)(=O)(O)[O-].C(C)[P+](C)(CC)CC MRCJOMGYXUMDTI-UHFFFAOYSA-M 0.000 description 1
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- NCIGEKFXLAUXKR-UHFFFAOYSA-M hydron;tetramethylphosphanium;sulfate Chemical compound [H+].C[P+](C)(C)C.[O-]S([O-])(=O)=O NCIGEKFXLAUXKR-UHFFFAOYSA-M 0.000 description 1
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- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
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- PSMNSLGWMXZFLO-UHFFFAOYSA-M methanesulfonate;methyl(trioctyl)azanium Chemical compound CS([O-])(=O)=O.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC PSMNSLGWMXZFLO-UHFFFAOYSA-M 0.000 description 1
- JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 description 1
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- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
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- 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
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- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
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- 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
- BOJSGWOJLRZTJR-UHFFFAOYSA-M triethyl(methyl)phosphanium;trifluoromethanesulfonate Chemical compound CC[P+](C)(CC)CC.[O-]S(=O)(=O)C(F)(F)F BOJSGWOJLRZTJR-UHFFFAOYSA-M 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
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- WCZKTXKOKMXREO-UHFFFAOYSA-N triethylsulfanium Chemical compound CC[S+](CC)CC WCZKTXKOKMXREO-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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- 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
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- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/30—Nitriles
- C08F222/32—Alpha-cyano-acrylic acid; Esters thereof
- C08F222/324—Alpha-cyano-acrylic acid butyl ester
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D135/04—Homopolymers or copolymers of nitriles
-
- 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
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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Abstract
Description
1.(a)2−シアノアクリル酸エステルと、(b)2−シアノアクリル酸エステルに相溶する高分子量成分と、(c)2−シアノ−3−ビニルアクリロイル基を2個以上有する多官能2−シアノ−3−ビニルアクリル酸エステルと、(d)下記一般式(1)で表されるオニウム塩と、を含有し、前記(b)、(c)及び(d)成分の含有量が、前記(a)成分を100質量部とした場合に、(b)成分は2〜50質量部、(c)成分は1〜200質量部、(d)成分は0.01〜5質量部であることを特徴とする接着剤組成物。
C+A- ・・・(1)
[式中、C+はオニウムカチオンであり、A-は実質的に2−シアノアクリル酸エステルの重合を開始しないアニオンである。]
2.前記(b)高分子量成分が、2−シアノアクリル酸エステルに難溶性の重合体となり得る単量体、及び、2−シアノアクリル酸エステルに可溶性の重合体となり得る単量体を用いてなる共重合体である上記1に記載の接着剤組成物。
3.2−シアノアクリル酸エステルに難溶性の重合体となり得る前記単量体が、エチレン、プロピレン、イソプレン及びブタジエンのうちの少なくとも1種であり、2−シアノアクリル酸エステルに可溶性の重合体となり得る前記単量体が、アクリル酸エステル及びメタクリル酸エステルのうちの少なくとも一方である上記2に記載の接着剤組成物。
4.前記(c)多官能2−シアノ−3−ビニルアクリル酸エステルが、ポリオキシアルキレンポリオール、ポリエステルポリオール、ポリカーボネートポリオール、ポリウレタンポリオール、ポリアミドポリオール、ポリエステルポリアミドポリオール、アクリルポリオール、ポリブタジエンポリオール、水添ポリブタジエンポリオール、エチレン−ブチレン共重合体ポリオール、ポリイソプレンポリオール、水添ポリイソプレンポリオール、ポリビニルブチラール、ポリビニルホルマール、ポリビニルアルコール、フェノール樹脂及び両末端にヒドロキシル基を有するシラン化合物又はシロキサン化合物の2−シアノ−3−ビニルアクリル酸エステルである上記1〜3のいずれかに記載の接着剤組成物。
5.前記(c)多官能2−シアノ−3−ビニルアクリル酸エステルの数平均分子量が、1000〜50000である上記1〜4のいずれかに記載の接着剤組成物。
6.前記一般式(1)で表されるオニウム塩のアニオンA-が、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1〜10のパーフルオロアルキル基、ビニル基、アリール基、パーフルオロアリール基、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、炭素数1〜10のパーフルオロアルキル基、アリール基である)上記1〜5のいずれかに記載の接着剤組成物。
7.硬化後に前記(a)2−シアノアクリル酸エステルの重合物が分散相、前記(b)高分子量成分が連続相となる海島構造を形成し、かつ、60℃で加熱処理後に、前記分散相の最大粒径の変化率が2倍以内である上記1〜6のいずれかに記載の接着剤組成物。
また、前記高分子量成分が2−シアノアクリル酸エステルに難溶性の重合体となり得る単量体及び2−シアノアクリル酸エステルに可溶性の重合体となり得る単量体を用いてなる共重合体である場合は、高いせん断接着強さを有するとともに、剥離接着強さ、衝撃接着強さも十分であり、より優れた耐冷熱サイクル性を有する接着剤組成物とすることができる。
更に、前記一般式(1)で示されるオニウム塩のアニオンが、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1〜10のパーフルオロアルキル基、ビニル基、アリール基、パーフルオロアリール基、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(R2はアルキル基、パーフルオロアルキル基、アリール基である)である場合には、多官能2−シアノ−3−ビニルアクリル酸エステルの硬化をより促進することにより、相分離構造が強固に固定され、より優れた耐冷熱サイクル性を有する接着剤組成物とすることができる。
本発明の接着剤組成物は、(a)2−シアノアクリル酸エステルと、(b)2−シアノアクリル酸エステルに相溶する高分子量成分と、(c)2−シアノ−3−ビニルアクリロイル基を2個以上有する多官能2−シアノ−3−ビニルアクリル酸エステルと、(d)前記一般式(1)で表されるオニウム塩と、を含有する接着剤組成物である。
各々のセグメントの割合は、プロトン核磁気共鳴分光法(以下「1H−NMR」と表記する)測定によるプロトンの積分値により算出することができる。
カルボキシル基含有セグメントの割合は、JIS K0070に準じ、電位差滴定法又は指示薬滴定法により測定することができる。
尚、本発明における平均分子量は、ゲルパーミエーションクロマトグラフィー(以下、「GPC」と略記する)で測定した値である。GPC測定の際には、テトラヒドロフランを移動相として、ポリスチレンゲルカラムを使用し、分子量の値はポリスチレン換算値で求めた。
C+A- ・・・(1)
[式中、C+はオニウムカチオンであり、A-は実質的に2−シアノアクリル酸エステルの重合を開始しないアニオンである。]
ここで、「実質的に2−シアノアクリル酸エステルの重合を開始しない」とは、2−シアノアクリル酸エステルと当該オニウム塩を混合した組成物(質量比;100/1)が、室温下で24時間ゲル化することなく、安定に存在することをいう。
尚、本発明の粒子の平均粒子径は、電気的検知帯式粒度分布測定装置、又はレーザー回折式粒度分布測定装置によって測定した値である。
[1]合成
(i)多官能2−シアノ−3−ビニルアクリル酸エステルの合成
・合成例1(化合物A)
攪拌機、温度計、リービッヒ冷却管、窒素吹き込み管及び滴下ロートを備える容量500ミリリットルのフラスコに、シアノ酢酸クロライド4.60g(45.2ミリモル)と、ベンゼン210ミリリットルとを仕込んだ。その後、反応系を60℃に昇温させ、窒素吹き込み管から窒素ガスを吹き込みながら、ポリプロピレングリコール[数平均分子量;4000(カタログ値)、ポリエ―テルトリオール型、ADEKA社製、商品名「アデカポリエーテルG−4000」]50.0g[当量比(酸クロ/OH基)=1.4]を50ミリリットルのベンゼンに溶解させた溶液を加えた。次いで、温度を60℃に維持し、30分間攪拌した。その後、室温(15〜35℃)まで冷却後、減圧下、ベンゼンを留去して、無色で粘ちょうなオイル状の多官能シアノ酢酸エステル51.5gを得た。
次に、攪拌機、温度計、リービッヒ冷却管、窒素吹き込み管及び滴下ロートを備える容量200ミリリットルのフラスコに、塩化亜鉛4.28g(31.4ミリモル)、先の反応で得られた多官能シアノ酢酸エステル44.0g、ハイドロキノン0.033g、ジオキサン60mlを仕込み、氷冷した。氷冷下攪拌しながら、90%アクロレイン9.56ml(62.8ミリモル)[当量比(アクロレイン/シアノアセチル基)=2/1]を滴下し、そのまま室温下で12時間攪拌した。氷冷下、石油エーテル120ml、1%亜硫酸水90mlを激しく攪拌しながら、反応液をゆっくり注ぎ、そのまま1時間攪拌した。有機相を無水硫酸マグネシウム上で乾燥後、減圧下で濃縮し、無色で粘稠なオイル状の多官能2−シアノ−3−ビニルアクリル酸エステルA42.1g(数平均分子量5240)を得た。
尚、ベンゼン、ジオキサンはそれぞれ乾燥ベンゼン、乾燥ジオキサンを使用し、ガラス器具は十分加熱乾燥させたものを用いた。
合成例1で用いたポリプロピレングリコールに代えて、数平均分子量が異なるポリプロピレングリコール[数平均分子量;3000(カタログ値)、両末端ヒドロキシル基型、ADEKA社製、商品名「アデカポリオールP−3000」]を使用し、化合物の数平均分子量及び官能基数に応じた仕込み量とした他は、合成例1と同様にして多官能2−シアノ−3−ビニルアクリル酸エステルB(数平均分子量3490)を合成した。
合成例1で用いたポリプロピレングリコールに代えて、数平均分子量が異なるポリプロピレングリコール[数平均分子量;10000(カタログ値)、両末端ヒドロキシル基型、旭硝子社製、商品名「プレミノールS−4011」]を使用し、化合物の数平均分子量及び官能基数に応じた仕込み量とした他は、合成例1と同様にして多官能2−シアノ−3−アクリル酸エステルC(数平均分子量15060)を合成した。
・合成例4(メチルトリ−n−オクチルアンモニウムトリフルオロメタンスルホネート) メチルトリ−n−オクチルアンモニウムクロリド(試薬、東京化成工業製)を用い、Hiroyuki Ohnoらの報告(J.Am.Chem.SOc.,2005,27,2398−2399)に基づき合成した。
実施例1
2−シアノアクリル酸イソブチルに、二酸化硫黄を40ppm、18−クラウン−6を100ppm、ハイドロキノンを1000ppm(2−シアノアクリル酸イソブチルを100質量部とする)配合し、これに更に表1に記載の、エチレン/アクリル酸メチル共重合体(デュポンエラストマー社製、商品名「Vamac DP」)、合成例1で得られた多官能2−シアノ−3−ビニルアクリル酸エステルA、合成例4で得られたオニウム塩X、及びヒュームドシリカ(日本アエロジル社製、商品名「アエロジル RY200」)を、表1に記載の含有量となるように配合し、温度20〜40℃で、15分間攪拌し、混合して接着剤組成物を製造した。
2−シアノアクリル酸エステルの種類、高分子量成分の種類及び含有量、2−シアノ−3−ビニルアクリル酸エステルの種類及び含有量、オニウム塩の種類及び含有量、ヒュームドシリカの種類及び含有量、並びにその他の添加剤の種類及び含有量が表1の記載となるように配合した他は、実施例1と同様にして接着剤組成物を製造した。
尚、表1における略号は、次の化合物を表す。
オニウム塩X:合成例4で合成したメチルトリ−n−オクチルアンモニウムトリフルオロメタンスルホネート
オニウム塩Y:メチルトリ−n−オクチルアンモニウムビス(トリフルオロメタンスルホニル)イミド(試薬)
オニウム塩Z:1−ブチル−3−メチルイミダゾリウム硫酸水素塩(試薬)
O−15:15−クラウン−5(試薬)
また、表2において、「E」はエチレン、「MA」はアクリル酸メチル、「AA」はアクリル酸、「AN」はアクリロニトリル、「BA」はアクリル酸ブチル、「St」はスチレンを表す。
更に、共重合体の組成のうちエチレンとアクリル酸エステルの比は前記の1H−NMR測定(日本電子社製、型式「ECA−400」を用いた)により、溶媒:重クロロホルム、温度:室温の条件で測定した値であり、アクリル酸の組成比はJIS K0070に準じ、酸価測定により求めた値である。
また、平均分子量は、GPC(ウォーターズ社製、型式「アライアンス2695」)により、[カラム:東ソー社製「TSKgel SuperMultiporeHZ−H」2本+東ソー社製「TSKgel SuperHZ−2500」2本連結、移動相:テトラヒドロフラン、測定温度:40℃、分子量の値はポリスチレン換算値である]の条件で測定した値である。
難接着であるポリエチレン基材上に、実施例1〜7及び比較例1〜5の接着剤組成物を塗布し(厚さ:20〜50μm)、温度23℃、湿度60%RHで7日間静置して完全硬化させた後、注意深く引き剥がし、接着剤硬化物を作製した(これを「初期」とする)。次いで、冷熱衝撃試験機を用いて、−40℃で1時間保持し、その後、80℃で1時間保持する冷熱サイクルを、接着剤硬化物に対して10サイクル行った(これを「試験後」とする)。
実施例1〜7及び比較例1〜5
上記の方法で得られた接着剤硬化物を切断した超薄切片の断面を、電界放出型走査電子顕微鏡(日立社製、型式「S−4800」、観察方法「SEM」及び「STEM」と表記)を用いて観察した。
尚、同一硬化物の複数個所を観察した中で、最も面積が大きい分散相に対し、同一面積の真円を仮定した場合の直径を、分散相の最大粒径とした。なお、分散相の面積は長軸の半径×短軸の半径×πで求めることができる。
尚、AFMでは位相遅れの大小が画像コントラストとなって現れるため、2−シアノアクリル酸エステルの重合物と高分子量成分の弾性率の差から、海島構造においてどちらが連続相を形成し、どちらが分散相を形成しているかを判断した。
アルミニウム板(JIS A6061Pに規定された材質)とABS樹脂製(ABS樹脂として新神戸電機社製、商品名「ABS−N−WN」を用いた)の試験片とを、実施例1〜7及び比較例1〜5の接着剤組成物を用いて接着させ、温度23℃、湿度60%RHで7日間静置して養生させた後、JIS K 6861に準じて引張せん断接着強さを測定した(これを初期強度とする)。次いで、冷熱衝撃試験機を用いて、−40℃で1時間保持し、その後、80℃で1時間保持する冷熱サイクルを1サイクルとして10サイクル後の引張せん断接着強さを上記と同様にして測定し(これを試験後強度とする)、下記のようにして保持率を算出した。結果は表4のとおりである。なお、比較例1の接着剤組成物を用いて接着した試験片を用い、冷熱サイクルの条件を−20℃で1時間保持後、60℃で1時間保持とし、5サイクル実施した以外、上記と同様の方法で試験後の強度を求め、保持率を計算したところ、試験後の強度は1.1N/mm2、保持率は10.9%であった。
保持率(%)=(試験後強度/初期強度)×100
Claims (7)
- (a)2−シアノアクリル酸エステルと、(b)2−シアノアクリル酸エステルに相溶する高分子量成分と、(c)2−シアノ−3−ビニルアクリロイル基を2個以上有する多官能2−シアノ−3−ビニルアクリル酸エステルと、(d)下記一般式(1)で表されるオニウム塩と、を含有し、
前記(b)、(c)及び(d)成分の含有量が、前記(a)成分を100質量部とした場合に、(b)成分は2〜50質量部、(c)成分は1〜200質量部、(d)成分は0.01〜5質量部であることを特徴とする接着剤組成物。
C+A- ・・・(1)
[式中、C+はオニウムカチオンであり、A-は実質的に2−シアノアクリル酸エステルの重合を開始しないアニオンである。] - 前記(b)高分子量成分が、2−シアノアクリル酸エステルに難溶性の重合体となり得る単量体、及び、2−シアノアクリル酸エステルに可溶性の重合体となり得る単量体を用いてなる共重合体である請求項1に記載の接着剤組成物。
- 2−シアノアクリル酸エステルに難溶性の重合体となり得る前記単量体が、エチレン、プロピレン、イソプレン及びブタジエンのうちの少なくとも1種であり、2−シアノアクリル酸エステルに可溶性の重合体となり得る前記単量体が、アクリル酸エステル及びメタクリル酸エステルのうちの少なくとも一方である請求項2に記載の接着剤組成物。
- 前記(c)多官能2−シアノ−3−ビニルアクリル酸エステルが、ポリオキシアルキレンポリオール、ポリエステルポリオール、ポリカーボネートポリオール、ポリウレタンポリオール、ポリアミドポリオール、ポリエステルポリアミドポリオール、アクリルポリオール、ポリブタジエンポリオール、水添ポリブタジエンポリオール、エチレン−ブチレン共重合体ポリオール、ポリイソプレンポリオール、水添ポリイソプレンポリオール、ポリビニルブチラール、ポリビニルホルマール、ポリビニルアルコール、フェノール樹脂及び両末端にヒドロキシル基を有するシラン化合物又はシロキサン化合物の2−シアノ−3−ビニルアクリル酸エステルである請求項1〜3のいずれか1項に記載の接着剤組成物。
- 前記(c)多官能2−シアノ−3−ビニルアクリル酸エステルの数平均分子量が、1000〜50000である請求項1〜4のいずれか1項に記載の接着剤組成物。
- 前記一般式(1)で表されるオニウム塩のアニオンA-が、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1〜10のパーフルオロアルキル基、ビニル基、アリール基、パーフルオロアリール基、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、炭素数1〜10のパーフルオロアルキル基、アリール基である)請求項1〜5のいずれか1項に記載の接着剤組成物。
- 硬化後に前記(a)2−シアノアクリル酸エステルの重合物が分散相、前記(b)高分子量成分が連続相となる海島構造を形成し、かつ、60℃で加熱処理後に、前記分散相の最大粒径の変化率が2倍以内である請求項1〜6のいずれか1項に記載の接着剤組成物。
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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 |
JP6241375B2 (ja) * | 2014-06-30 | 2017-12-06 | 東亞合成株式会社 | 着色された2−シアノアクリレート系接着剤組成物 |
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 |
CN106039391A (zh) * | 2016-06-21 | 2016-10-26 | 林春梅 | 一种抗菌高粘合医用胶水及其制备方法 |
GB2562107B (en) | 2017-05-05 | 2021-08-11 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
GB2567219B (en) * | 2017-10-06 | 2021-08-11 | Henkel IP & Holding GmbH | Thermoplastic polyurethane toughened cyanoacrylate compositions |
CN108452369B (zh) * | 2018-06-21 | 2021-02-09 | 浙江派菲特新材料科技有限公司 | 一种高抗菌性能医用粘合剂的制备方法 |
JP2021025012A (ja) * | 2019-08-08 | 2021-02-22 | 東亞合成株式会社 | 布地、皮革又は紙用接着剤、布地、皮革又は紙の接着方法、及び布地、皮革又は紙製品の製造方法 |
CN113827765A (zh) * | 2021-09-24 | 2021-12-24 | 南通伊诺精密塑胶导管有限公司 | 一种植入型氰基丙烯酸酯医用胶及其应用 |
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