JP6273536B2 - 接着剤組成物 - Google Patents
接着剤組成物 Download PDFInfo
- Publication number
- JP6273536B2 JP6273536B2 JP2015535399A JP2015535399A JP6273536B2 JP 6273536 B2 JP6273536 B2 JP 6273536B2 JP 2015535399 A JP2015535399 A JP 2015535399A JP 2015535399 A JP2015535399 A JP 2015535399A JP 6273536 B2 JP6273536 B2 JP 6273536B2
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- JP
- Japan
- Prior art keywords
- group
- adhesive composition
- acid
- polymer
- cyanoacrylate
- 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.)
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- 239000000853 adhesive Substances 0.000 title claims description 93
- 230000001070 adhesive effect Effects 0.000 title claims description 93
- 239000000203 mixture Substances 0.000 title claims description 81
- -1 2-cyanoacrylic acid ester Chemical class 0.000 claims description 138
- 229920000642 polymer Polymers 0.000 claims description 79
- 239000000178 monomer Substances 0.000 claims description 51
- 229920001577 copolymer Polymers 0.000 claims description 47
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 42
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 40
- 229920001971 elastomer Polymers 0.000 claims description 34
- 239000000806 elastomer Substances 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 22
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 20
- 239000003377 acid catalyst Substances 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 17
- 150000001768 cations Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 7
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 7
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229940079826 hydrogen sulfite Drugs 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
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 22
- 239000000377 silicon dioxide Substances 0.000 description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 14
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 7
- 229910021485 fumed silica Inorganic materials 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000034 method Methods 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 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
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000007373 indentation Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229940079877 pyrogallol Drugs 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 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
- 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 2
- WACRAFUNNYGNEQ-UHFFFAOYSA-N 1-ethyl-1-methylpiperidin-1-ium Chemical compound CC[N+]1(C)CCCCC1 WACRAFUNNYGNEQ-UHFFFAOYSA-N 0.000 description 2
- IRGDPGYNHSIIJJ-UHFFFAOYSA-N 1-ethyl-2,3-dimethylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1C IRGDPGYNHSIIJJ-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
- 238000005160 1H NMR spectroscopy Methods 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
- CQBZHSCDPNAGLN-UHFFFAOYSA-N 2-heptyl-1,3-dimethylimidazol-1-ium Chemical compound CCCCCCCC=1N(C)C=C[N+]=1C CQBZHSCDPNAGLN-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
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-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
- JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical compound CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 2
- 208000034189 Sclerosis Diseases 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 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
- 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
- 239000004202 carbamide Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 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 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
- 229940078672 didecyldimethylammonium Drugs 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
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- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 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
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- 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 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- 238000002715 modification method Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 239000002245 particle Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000013500 performance material Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
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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
- 238000007654 immersion Methods 0.000 description 1
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- QRWOVIRDHQJFDB-UHFFFAOYSA-N isobutyl cyanoacrylate Chemical compound CC(C)COC(=O)C(=C)C#N QRWOVIRDHQJFDB-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NNCAWEWCFVZOGF-UHFFFAOYSA-N mepiquat Chemical compound C[N+]1(C)CCCCC1 NNCAWEWCFVZOGF-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- VQKXPQHMUTZSJA-UHFFFAOYSA-M methanesulfonate;1-methyl-1-propylpyrrolidin-1-ium Chemical compound CS([O-])(=O)=O.CCC[N+]1(C)CCCC1 VQKXPQHMUTZSJA-UHFFFAOYSA-M 0.000 description 1
- 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
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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- COYQOLYIVUYLFQ-UHFFFAOYSA-N methyl-di(propan-2-yl)-propylazanium Chemical compound CCC[N+](C)(C(C)C)C(C)C COYQOLYIVUYLFQ-UHFFFAOYSA-N 0.000 description 1
- NAYLGVYVQMVNFY-UHFFFAOYSA-N methyl-tri(propan-2-yl)azanium Chemical compound CC(C)[N+](C)(C(C)C)C(C)C NAYLGVYVQMVNFY-UHFFFAOYSA-N 0.000 description 1
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
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- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000003136 n-heptyl 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])* 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- HTKPDYSCAPSXIR-UHFFFAOYSA-N octyltrimethylammonium ion Chemical compound CCCCCCCC[N+](C)(C)C HTKPDYSCAPSXIR-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
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- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
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- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
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- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- YNJQKNVVBBIPBA-UHFFFAOYSA-M tetrabutylazanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[N+](CCCC)(CCCC)CCCC YNJQKNVVBBIPBA-UHFFFAOYSA-M 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- PUZYNDBTWXJXKN-UHFFFAOYSA-M tetraethylazanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC[N+](CC)(CC)CC PUZYNDBTWXJXKN-UHFFFAOYSA-M 0.000 description 1
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- 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
- QPWLXCIPMHWOHD-UHFFFAOYSA-M tetramethylphosphanium;trifluoromethanesulfonate Chemical compound C[P+](C)(C)C.[O-]S(=O)(=O)C(F)(F)F QPWLXCIPMHWOHD-UHFFFAOYSA-M 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
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- 125000005425 toluyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- 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
- 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 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
- LAGQNGWYNLUQRI-UHFFFAOYSA-N trioctylmethylammonium bis(trifluoromethylsulfonyl)imide Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC LAGQNGWYNLUQRI-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
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 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
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
- C08F222/322—Alpha-cyano-acrylic acid ethyl ester, e.g. ethyl-2-cyanoacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C09J121/00—Adhesives based on unspecified rubbers
-
- 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
-
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Description
従来、このような問題点を改良するため、種々の可塑剤及びエラストマー等を配合する改質方法が提案されている(例えば、特許文献1、2及び3)。また、難溶性のゴムやエラストマー粒子を配合する方法も提案されている(例えば、特許文献4)。更に、2−シアノアクリル酸エステルと常温湿気硬化型接着剤との2種類の接着剤を使用して、短時間に被着体を仮止めし、一定時間経過後に十分な接着強さが得られる接着方法も開示されている(例えば、特許文献5)。
一方、当該接着剤の耐水性を改善するため、2−シアノアクリル酸エステルにモノシラン化合物やビスシラン化合物を配合することが知られている(例えば、特許文献6)。
1.(a)2−シアノアクリル酸エステルと、(b)加水分解性シリル基を有する重合体と、(c)エラストマーと、(d)酸触媒とを含有し、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5〜200質量部、(c)成分は5〜50質量部、(d)成分は0.0005〜0.5質量部であることを特徴とする接着剤組成物。
2.上記(b)加水分解性シリル基を有する重合体の主鎖骨格が、オキシアルキレン系重合体、ビニル系重合体、ポリエステル系重合体、ポリウレタン系重合体、及びポリカーボネート系重合体からなる群より選択される少なくとも1種の重合体である上記1に記載の接着剤組成物。
3.上記(b)加水分解性シリル基を有する重合体の数平均分子量が、500〜50000である上記1又は2に記載の接着剤組成物。
4.上記(c)エラストマーが、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1〜3のいずれかに記載の接着剤組成物。
5.上記(c)エラストマーが、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、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、及びカルボキシ基含有単量体とを用いてなる共重合体である上記1〜3のいずれかに記載の接着剤組成物。
6.上記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、上記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4又は5に記載の接着剤組成物。
7.上記(d)酸触媒は、25℃におけるpKaが4以下の酸である上記1〜6のいずれかに記載の接着剤組成物。
8.上記(d)酸触媒が、スルホン酸、リン酸、リン酸モノエステル、リン酸ジエステル、亜リン酸、及び亜リン酸エステルからなる群より選択される少なくとも1種の酸である上記1〜7のいずれかに記載の接着剤組成物。
9.更に、(e)下記一般式(1)で表されるオニウム塩を含有する上記1〜8のいずれかに記載の接着剤組成物。
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、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)、(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、もしくはアリール基である)、テトラフルオロホウ素アニオン、又はヘキサフルオロリン酸アニオンである。]
10.上記(e)オニウム塩のカチオンが、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1種のオニウムカチオンである上記9に記載の接着剤組成物。
11.上記(e)オニウム塩の含有量が、(a)2−シアノアクリル酸エステルを100質量部とした場合に、0.001〜5質量部である上記9又は10に記載の接着剤組成物。
更に、接着剤組成物が一般式(1)で表されるオニウム塩を含有する場合は、接着剤組成物が硬化性に優れ、かつ、良好な貯蔵安定性が得られる。
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、(b)加水分解性シリル基を有する重合体、(c)エラストマー、及び(d)酸触媒を特定量含有する接着剤組成物である。
−O−R11− (3)
(式中、R11は、2価の炭化水素基である。)
なお、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」と略す)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。
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。
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、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)、(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、もしくはアリール基である)、テトラフルオロホウ素アニオン、又はヘキサフルオロリン酸アニオンである。]
また、接着剤硬化物の外観が問題となる場合は、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)。]が好ましい。硬化物の白濁が起こらず、かつ、優れた硬化速度を発現するからである。
1.評価方法
(1)分子量
装置:アライアンス2695(ウォーターズ社製)
カラム:TSKgel SuperMultiporeHZ−H 2本、TSKgel SuperHZ−2500 2本連結(東ソー社製)
カラム温度: 40℃
溶離液: テトラヒドロフラン 0.35ml/min
検出器: RI
GPCにより測定した分子量をポリスチレンの分子量を基準にして換算した。
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。
・ABS:宇部サイコン社製ABS樹脂、商品名「GSE」
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1〜14及び比較例1〜3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。
保持率(%)=(試験後強度/初期強度)×100
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1〜14及び比較例1〜3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、60℃での温水に1週間浸漬後の引張り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。
保持率(%)=(試験後強度/初期強度)×100
0.1mm厚のアルミニウム箔(JIS 1N30に規定された材質)を試験片とし、実施例1〜14及び比較例1〜3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 6854−3に準じてT形はく離接着強さを測定した。
1mm厚の硬化物を作製し、圧子押込超微小硬度計(フィッシャー インストロメンツ社製 商品名「H100CXYp」)により、押し込み荷重200mN、保持時間10秒の条件下で、ユニバーサル硬さを測定した。
合成例1(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)
50mlナス型フラスコにメチルトリ−n−オクチルアンモニウムクロリド(試薬)4.041g(10.00mmol)、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)、トルエン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、氷冷下でトリフルオロメタンスルホン酸1.501g(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。これをイオン交換水25mlで3回洗浄し、更に無水硫酸ナトリウム上で乾燥後、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、淡黄色半固体5.022g(オニウム塩A)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部とする)、酸触媒としてメタンスルホン酸(キシダ化学社製、試薬、pKa=−0.6[25℃])0.005部配合する。これに表1に記載のエラストマー(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 G」)20部を溶解させた後、予めビニルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製、商品名「A−171」)1.5部を混合した、加水分解性シリル基を有する重合体50質量部(カネカ社製、商品名「サイリルSAT200」)を、表1に記載の含有量となるように配合し、温度15〜30℃で、10分間攪拌し、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、上記評価行った。結果を表2に示す。
2−シアノアクリル酸エチルに、酸触媒の種類と含有量、エラストマーの種類(デュポンエラストマー社製 商品名「Vamac」シリーズ、表3参照)及び含有量、加水分解性シリル基を有する重合体の種類及び含有量(カネカ社製 商品名「サイリル」シリーズ、表4参照)、が表1の記載となるように配合した以外は、実施例1と同様にして接着剤組成物を製造し、評価した。酸触媒であるリン酸ジブチルのpKaは1.72(25℃)である。結果を表2に示す。
なお、表3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、「BA」はアクリル酸ブチルを表す。
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部とする)、メタンスルホン酸を0.09部配合する。これに更に表5に記載のエラストマー(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 G」)を溶解させた後、予めビニルトリメトキシシラン(モメンティブ パフォーマンス・マテリアルズ・ジャパン社製、商品名「A−171」)1.5部を混合した、加水分解性シリル基を有する重合体(カネカ社製、商品名「サイリルSAT200」)、合成例1で得られたオニウム塩Aを、表5に記載の含有量となるように配合し、温度15〜30℃で、10分間攪拌し、混合して接着剤組成物を製造し、実施例1と同様に評価した。結果を表6に示す。
2−シアノアクリル酸エチル(実施例13及び14では2−シアノアクリル酸イソブチルと混合)に、酸触媒の種類と含有量、エラストマーの種類(デュポンエラストマー社製 商品名「Vamac」シリーズ、表3参照)及び含有量、加水分解性シリル基を有する重合体の種類及び含有量(カネカ社製 商品名「サイリル」シリーズ、表4参照)、オニウム塩の種類及び含有量が表5の記載となるように配合した以外は、実施例1と同様にして接着剤組成物を製造し、評価した。結果を表6に示す。
エラストマーを配合しなかった以外は実施例1と同様に製造を行ったが、2−シアノアクリル酸エステルと加水分解性シリル基を有する重合体が混合できず、すぐに発熱、ゲル化したため、評価に至らなかった、
酸触媒を配合しなかった以外は実施例1と同様に製造を行った。2−シアノアクリル酸エステルと加水分解性シリル基を有する重合体を混合することはできたが、すぐに増粘、ゲル化したため評価に至らなかった。
加水分解性シリル基を有する重合体を配合しなかった以外は実施例1と同様に製造を行い、同様に評価を行った。結果を表8に示す。
Claims (9)
- (a)2−シアノアクリル酸エステルと、(b)加水分解性シリル基を有する重合体と、(c)エラストマーと、(d)酸触媒とを含有し、
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5〜200質量部、(c)成分は5〜50質量部、(d)成分は0.0005〜0.5質量部であって、
前記(b)加水分解性シリル基を有する重合体の主鎖骨格がオキシアルキレン系重合体であり、
前記(c)エラストマーが、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ことを特徴とする接着剤組成物。 - 上記(b)加水分解性シリル基を有する重合体の数平均分子量が、500〜50000である請求項1に記載の接着剤組成物。
- 上記(c)エラストマーが、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、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、及びカルボキシ基含有単量体を用いてなる共重合体である請求項1又は2に記載の接着剤組成物。
- 上記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、上記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1〜3のいずれか1項に記載の接着剤組成物。
- 上記(d)酸触媒は、25℃におけるpKaが4以下の酸である請求項1〜4のいずれか1項に記載の接着剤組成物。
- 上記(d)酸触媒が、スルホン酸、リン酸、リン酸モノエステル、リン酸ジエステル、亜リン酸、及び亜リン酸エステルからなる群より選択される少なくとも1種の酸である請求項1〜5のいずれか1項に記載の接着剤組成物。
- 更に、(e)下記一般式(1)で表されるオニウム塩を含有する請求項1〜6のいずれか1項に記載の接着剤組成物。
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、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)、(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、もしくはアリール基である)、テトラフルオロホウ素アニオン、又はヘキサフルオロリン酸アニオンである。] - 上記(e)オニウム塩のカチオンが、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1種のオニウムカチオンである請求項7に記載の接着剤組成物。
- 上記(e)オニウム塩の含有量が、(a)2−シアノアクリル酸エステルを100質量部とした場合に、0.001〜5質量部である請求項7又は8に記載の接着剤組成物。
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