JPH03167279A - Instantaneous adhesive composition - Google Patents
Instantaneous adhesive compositionInfo
- Publication number
- JPH03167279A JPH03167279A JP30723989A JP30723989A JPH03167279A JP H03167279 A JPH03167279 A JP H03167279A JP 30723989 A JP30723989 A JP 30723989A JP 30723989 A JP30723989 A JP 30723989A JP H03167279 A JPH03167279 A JP H03167279A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- crown
- ester
- water resistance
- cyano
- 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 45
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 45
- 239000000203 mixture Substances 0.000 title claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 31
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 21
- 150000003983 crown ethers Chemical class 0.000 claims abstract description 7
- -1 2-cyanoacrylic acid ester Chemical class 0.000 claims description 55
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 25
- 150000002148 esters Chemical class 0.000 abstract description 14
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 abstract description 4
- 229920001451 polypropylene glycol Polymers 0.000 abstract description 4
- FHVDNOQFWFJILR-UHFFFAOYSA-N methyl 2-cyanopenta-2,4-dienoate Chemical compound COC(=O)C(C#N)=CC=C FHVDNOQFWFJILR-UHFFFAOYSA-N 0.000 abstract description 2
- 238000013329 compounding Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920002943 EPDM rubber Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 238000007747 plating Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 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
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 125000001117 oleyl 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])=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 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluenecarboxylic acid Natural products CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012756 surface treatment agent Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SDVVLIIVFBKBMG-ONEGZZNKSA-N (E)-penta-2,4-dienoic acid Chemical class OC(=O)\C=C\C=C SDVVLIIVFBKBMG-ONEGZZNKSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- UYVWNPAMKCDKRB-UHFFFAOYSA-N 1,2,4,5-tetraoxane Chemical compound C1OOCOO1 UYVWNPAMKCDKRB-UHFFFAOYSA-N 0.000 description 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- RZYHXKLKJRGJGP-UHFFFAOYSA-N 2,2,2-trifluoro-n,n-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)N([Si](C)(C)C)C(=O)C(F)(F)F RZYHXKLKJRGJGP-UHFFFAOYSA-N 0.000 description 1
- AXWCVSOBRFLCJG-UHFFFAOYSA-N 2,5,12,15,22,25-hexaoxatetracyclo[24.4.0.06,11.016,21]triaconta-1(30),6,8,10,16,18,20,26,28-nonaene Chemical compound O1CCOC2=CC=CC=C2OCCOC2=CC=CC=C2OCCOC2=CC=CC=C21 AXWCVSOBRFLCJG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HTRVTKUOKQWGMO-UHFFFAOYSA-N 2-ethyloctan-1-ol Chemical compound CCCCCCC(CC)CO HTRVTKUOKQWGMO-UHFFFAOYSA-N 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- AUKCYOUETBBMFV-UHFFFAOYSA-N 3-trimethylsilyl-1,3-oxazolidin-2-one Chemical compound C[Si](C)(C)N1CCOC1=O AUKCYOUETBBMFV-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- FBADCSUQBLLAHW-UHFFFAOYSA-N 4-trimethylsilyloxypent-3-en-2-one Chemical compound CC(=O)C=C(C)O[Si](C)(C)C FBADCSUQBLLAHW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 1
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
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- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
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- 239000006087 Silane Coupling Agent Substances 0.000 description 1
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- 229920006311 Urethane elastomer Polymers 0.000 description 1
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- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229940090012 bentyl Drugs 0.000 description 1
- FNEPSTUXZLEUCK-UHFFFAOYSA-N benzo-15-crown-5 Chemical compound O1CCOCCOCCOCCOC2=CC=CC=C21 FNEPSTUXZLEUCK-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
- JMSRBKPMLUGHCR-UHFFFAOYSA-N bromohydrin Chemical compound BrC[C]1CO1 JMSRBKPMLUGHCR-UHFFFAOYSA-N 0.000 description 1
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- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
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- 150000001983 dialkylethers Chemical class 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
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- CURUTKGFNZGFSE-UHFFFAOYSA-N dicyclomine Chemical group C1CCCCC1C1(C(=O)OCCN(CC)CC)CCCCC1 CURUTKGFNZGFSE-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
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- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940063557 methacrylate Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- KAHVZNKZQFSBFW-UHFFFAOYSA-N n-methyl-n-trimethylsilylmethanamine Chemical compound CN(C)[Si](C)(C)C KAHVZNKZQFSBFW-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
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Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
（イ）発明の目的
「産業上の利用分野」
本発明は２−シアノアクリル酸エステルを主成分とする
瞬間接着剤ｍ威物に関するものであり、金属、プラスチ
ック、ゴム、セラξツク、木材等の種々材料において優
れた速硬化性と接着強さを有し、かつ高度な耐水性を有
する瞬間接着剤組成物を提供するものである。Detailed Description of the Invention (a) Object of the invention "Field of industrial application" The present invention relates to an instant adhesive containing 2-cyanoacrylic acid ester as a main component, and is applicable to metals, plastics, rubber, etc. The object of the present invention is to provide an instant adhesive composition that has excellent fast curing properties and adhesive strength on various materials such as ceramics, wood, etc., and has a high degree of water resistance.
２−シアノアクリル酸エステルを主或分とする瞬間接着
剤は被着材表面の吸着水分等により容易にアニオン重合
して急速に硬化するという性質を有するため、従来より
広く各種産業界、医療分野、レジャー分野、さらには一
般家庭において賞用されている．本発明の接着剤組成物
は従来の瞬間接着剤と同様にこれらの分野で巾広く利用
できる上に、その優れた耐水性からさらに多くの用途に
使用されうるものである．
「従来の技術」
２−シアノアクリル酸エステル系の瞬間接着剤の接着耐
水性を高める方法は従来より種々検討されている．その
一つの方法として２−シアノアクリル酸エステルに対し
５０重景％を超え、かつ９５重量％以下の量の下記一般
式で示される１，１−ジ置換ジエンを添加する方法（特
公昭６２−２８８３５）が提案されている。Instant adhesives mainly composed of 2-cyanoacrylic acid esters have the property of easily anionically polymerizing and rapidly curing due to adsorbed moisture on the surface of adherends, so they are widely used in various industries and medical fields. It has been widely used in the leisure field and even at home. The adhesive composition of the present invention, like conventional instant adhesives, can be widely used in these fields, and because of its excellent water resistance, it can be used in many more applications. ``Prior Art'' Various methods have been studied to improve the adhesive water resistance of 2-cyanoacrylic acid ester instant adhesives. One method is to add a 1,1-disubstituted diene represented by the following general formula in an amount of more than 50 weight percent and less than 95 weight percent to 2-cyanoacrylic acid ester (Japanese Patent Publication No. 62 28835) has been proposed.
Ｙ
ｌ １ ＼
ＲｔＲｚ Ｙ
（式中、Ｒ，は水素、炭素数１〜５のアルキル基、アリ
ール基、アラルキル基、またはハロゲンであり、Ｒ２は
水素、または炭素数１〜５のアルキル基であり、Ｘ及び
Ｙはそれぞれ、同一かまたは異なるものであり、シアノ
基、カルボン酸エステル基より選ばれる）
この他にも２−シアノアクリル酸エステルにジカルボン
酸やα−ケトカルボン酸を添加する方法（特公昭５８−
１８９５５、特公昭５Ｂ−３０９０８）、ジメチルビニ
ルエチニルカルビノール・フッ素化エーテルを添加する
方法（特公昭５９−１４５１０）、２−シアノアクリル
酸エステルのアルキル基にフッ素を導入する方法（特公
昭４７−２５１３９、特公昭４７−２９４８８）が提案
されている．
「発明が解決しようとする問題点」
上記の方法のうち特公昭６２−．２８８３５号公報記載
の方法によれば、かなりよい耐水性が得られる．しかし
ながら、アニオン重合性が２−シアノアクリル酸エステ
ルよりもはるかに小さい２−シアノ−２，４−ペンタジ
エン酸エステル等の１．１−ジ置換ジエンを多く含むた
めに接着速度が遅いという問題点がある。十分な接着速
度を得るために安定剤の量を減らしたり、硬化促進剤を
添加したりすると組成物の貯蔵安定性が著しく低下する
。また、１．１−ジ置換ジエン単位が多くなると硬化物
の極性が低下し金属類への接着性が低下するという問題
点がある．
一方、前記以外の方法では実用的な耐水性を得ることは
できない。２−シアノアクリル酸エステノレの重合体は
加水分解性の重合体であるために、改質剤の添加やアル
キル基へのフ・冫素導入だけでは十分な耐水性が得られ
ないものと考えられる。Y l 1 \ RtRz Y (wherein, R is hydrogen, an alkyl group having 1 to 5 carbon atoms, an aryl group, an aralkyl group, or a halogen; R2 is hydrogen or an alkyl group having 1 to 5 carbon atoms; . Kosho 58-
18955, Japanese Patent Publication No. 5B-30908), a method of adding dimethyl vinyl ethynyl carbinol fluorinated ether (Japanese Patent Publication No. 59-14510), a method of introducing fluorine into the alkyl group of 2-cyanoacrylic acid ester (Japanese Patent Publication No. 47-1982) 25139, Special Publication No. 47-29488) has been proposed. "Problems to be solved by the invention" Among the above methods, Japanese Patent Publication No. 1983-. According to the method described in Publication No. 28835, fairly good water resistance can be obtained. However, the problem is that the adhesion speed is slow because it contains a large amount of 1,1-disubstituted dienes such as 2-cyano-2,4-pentadienoic acid ester, which has much lower anionic polymerizability than 2-cyanoacrylic acid ester. be. If the amount of stabilizer is reduced or a curing accelerator is added to obtain a sufficient adhesion speed, the storage stability of the composition will be significantly reduced. Furthermore, when the 1,1-disubstituted diene units increase, the polarity of the cured product decreases, resulting in a decrease in adhesion to metals. On the other hand, practical water resistance cannot be obtained by methods other than those described above. Since the polymer of 2-cyanoacrylate ester is a hydrolyzable polymer, it is thought that sufficient water resistance cannot be obtained only by adding a modifier or introducing fluorine into the alkyl group. .
本発明の目的は、従来技術のこのような問題点を解決し
、優れた速硬化性、接着強さを有し、かつ高度な耐水性
を有する瞬間接着剤組威物を提供することにある。The purpose of the present invention is to solve these problems of the prior art and provide an instant adhesive composition that has excellent fast curing properties, adhesive strength, and high water resistance. .
（ロ）発明の構或
「問題点を解決するための手段」
本発明者らは上記問題点の解決のため鋭意検討を重ねた
結果、２−シアノアクリル酸エステルに２−シアノ−２
．４−ペンタジエン酸エステル、疎水性シリカと特定の
硬化促進剤を併用することにより、上記問題点がことご
とく解決されることを見いだし本発明を完威した．
すなわち、本発明は、次の４成分からなることを特徴と
する瞬間接着剤組戒物に関するものである。(B) Structure of the Invention or "Means for Solving the Problems" As a result of intensive studies to solve the above problems, the present inventors found that 2-cyano-2
．． We have found that all of the above problems can be solved by using 4-pentadienoic acid ester, hydrophobic silica, and a specific curing accelerator in combination, and have completed the present invention. That is, the present invention relates to an instant adhesive composition characterized by comprising the following four components.
（ｌ）２−シアノアクリル酸エステル
（２）２−シアノ−２．４−ペンタジエン酸エステル（
３〉 疎水性シリカ
（４） クラウンエーテル、ポリアルキレンオキサイ
ドまたはその誘導体
本発明の瞬間接着剤組或物によれば、優れた速硬化性と
接着強さを有し、かつ高度な耐水性を有する接着剤を提
供できるものである。(l) 2-cyanoacrylic acid ester (2) 2-cyano-2,4-pentadienoic acid ester (
3> Hydrophobic silica (4) Crown ether, polyalkylene oxide or derivative thereof According to the instant adhesive composition of the present invention, it has excellent fast curing properties and adhesive strength, and has a high degree of water resistance. It can provide adhesives.
０２−シアノアクリル酸エステル
本発明に使用される２−シアノアクリル酸エステルとし
ては、通常瞬間接着剤に使用されている全てのものが含
まれる。02-Cyanoacrylic ester The 2-cyanoacrylic ester used in the present invention includes all those commonly used in instant adhesives.
具体的には、メチル、エチル、プロビル、イソブロビル
、プチル、イソブチル、ｓｅｃ−プチル、ベンチル、ヘ
キシル、シクロヘキシル、２−メトキシエチル、２−エ
トキシエチル等のエステルを挙げることができる。Specifically, esters such as methyl, ethyl, proyl, isobrobyl, butyl, isobutyl, sec-butyl, bentyl, hexyl, cyclohexyl, 2-methoxyethyl, and 2-ethoxyethyl can be mentioned.
０２−シアノ−２．４−ペンタジエン酸エステル本発明
に使用される２−シアノ−２．４−ペンタジエン酸エス
テルとしては、具体的にはメチル、エチル、プロビル、
イソプロビル、ブチル、イソブチル、ｓｅｃ−７’チル
、ペンチル、ヘキシル、ヘブチル、オクチル、シクロヘ
キシル等のエステルを挙げることができる。エステル基
が大きくなるのにともない速硬化性、接着強さ、耐水性
がいずれも低下する傾向にあるので、本発明にとり好ま
しいものとしてはメチル、エチル、プロビル、イソプロ
ビル、ブチル、イソブチル、ｓｅｃ−ブチルのエステル
を挙げることが出来る。02-cyano-2.4-pentadienoic acid ester The 2-cyano-2.4-pentadienoic acid ester used in the present invention specifically includes methyl, ethyl, probyl,
Esters such as isopropyl, butyl, isobutyl, sec-7'tyl, pentyl, hexyl, hebutyl, octyl, cyclohexyl and the like can be mentioned. As the size of the ester group increases, fast curing properties, adhesive strength, and water resistance all tend to decrease, so methyl, ethyl, probyl, isopropyl, butyl, isobutyl, and sec- Mention may be made of esters of butyl.
○疎水性シリカ
本発明において用いられる疎水性シリカは、親水性シリ
カの表面に存在する水酸基と何等かの形で反応し疎水基
を形成し得る化合物又は親水性シリカの表面に吸着され
該表面に疎水性の層を形威し得る化合物（以下表面処理
剤という）と親水性シリカを、溶媒の共存下又は不存在
下に接触させ、好ましくは加熱することにより親水性シ
リカの表面を疎水性に変化させて得られるものである，
原料となる親水性シリカとしては、ヒュームドシリカや
湿式シリカ等が挙げられ、一次粒子の粒径がｉ−ｔｏｏ
μｍのものが好ましく、５〜５０μｍのものがより好ま
しい。この様な微粒子シリカとしては、例えば、四塩化
珪素を酸水素焔中で加水分解することにより得られる、
高分散性の無定形シリカがある。又、酸水素焔中で加水
分解させる際に、塩化チタニウム、塩化アル逅ニウム、
塩化鉄などの塩化物を併存させアルミナ含有シリカ、酸
化チタン含有シリカ、酸化鉄含有シリカとしたものも本
発明で用いることができる．親水性シリカの表面状態を
変化させ疎水性シリカとする表面処理剤としては、ｎ−
オクチルトリアルコキシシランなどの疎水基を有するア
ルキル、アリール、アラルキル系シランカップリング剤
、ジメチルジク口ロシラン、ヘキサメチルジシラザン等
のシリル化剤、ポリジメチルシロキサン等のシリコーン
オイル、ステアリルアルコール等の高級アルコール、ス
テアリン酸等の高級脂肪酸等が挙げられる．
本発明においては疎水性シリカとして、親水性シリカの
表面にジメチルシリル基又はトリメチルシリル基を付加
し得る、所謂、ジメヂルシリル化剤又はトリメチルシリ
ル化剤で表面処理された親木性シリカより得られる疎水
性シリカを用いるのが好ましい。○Hydrophobic silica The hydrophobic silica used in the present invention is a compound that can react in some form with the hydroxyl group present on the surface of hydrophilic silica to form a hydrophobic group, or a compound that is adsorbed to the surface of hydrophilic silica and attached to the surface. A compound capable of forming a hydrophobic layer (hereinafter referred to as a surface treatment agent) is brought into contact with hydrophilic silica in the presence or absence of a solvent, and the surface of the hydrophilic silica is made hydrophobic by preferably heating. It is obtained by changing
Examples of the hydrophilic silica used as a raw material include fumed silica and wet silica, and the particle size of the primary particles is i-too.
Preferably, the thickness is 5 to 50 μm, and more preferably 5 to 50 μm. Such fine particle silica can be obtained, for example, by hydrolyzing silicon tetrachloride in an oxyhydrogen flame.
There is highly dispersed amorphous silica. Also, when hydrolyzed in an oxyhydrogen flame, titanium chloride, aluminum chloride,
Alumina-containing silica, titanium oxide-containing silica, and iron oxide-containing silica in which a chloride such as iron chloride is present can also be used in the present invention. As a surface treatment agent that changes the surface condition of hydrophilic silica to make it hydrophobic silica, n-
Alkyl, aryl, aralkyl-based silane coupling agents having hydrophobic groups such as octyltrialkoxysilane, silylating agents such as dimethyldimethylsilane and hexamethyldisilazane, silicone oils such as polydimethylsiloxane, higher alcohols such as stearyl alcohol, Examples include higher fatty acids such as stearic acid. In the present invention, the hydrophobic silica is hydrophobic silica obtained from wood-philic silica surface-treated with a so-called dimethylsilylating agent or trimethylsilylating agent, which can add a dimethylsilyl group or a trimethylsilyl group to the surface of the hydrophilic silica. It is preferable to use
ジメチルシリル化剤及びトリメチルシリル化剤の具体例
としては、上記のジメチルジクロロシラン、ヘキサメチ
ルジシラザンの他にジメチルジメトキシシラン、ジメチ
ルジエトキシシラン、ジメチルジアセトキシシラン、ジ
メチルジトリフルオロアセトキシシラン、ヘキサメチル
シクロトリシラザン、トリメチルクロロシラン、トリメ
チルブロモシラン、Ｎ，０−ビス（トリメチルシリル）
カーバメート、Ｎ，Ｎ−ジエチルア壽ノトリメチルシラ
ン、Ｎ，Ｎ−ジメチルアミノトリメチルシラン、ヘキサ
メチルジシロキサン、Ｎ一トリメチルシリルイミダゾー
ル、ビス（トリメチルシリル）アセトアξド、ビス（ト
リメチルシリル）トリフルオロアセトアミド、ビス（ト
リメチルシリル）ウレア、２−トリメチルシロキシ−２
−ペンテン−４−オン、トリメチルシリルアセトアξド
、トリメチルシリルーＮＳＮ’−ジフエニルウレア、３
−トリメチルシリルー２−オキサゾリジノン、ビス（ト
リメチルシロキシ）ジメチルシラン等を挙げることがで
きる。Specific examples of the dimethylsilylating agent and trimethylsilylating agent include dimethyldichlorosilane, hexamethyldisilazane, dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldiacetoxysilane, dimethylditrifluoroacetoxysilane, and hexamethylcyclosilane. Trisilazane, trimethylchlorosilane, trimethylbromosilane, N,0-bis(trimethylsilyl)
Carbamate, N,N-diethylaminotrimethylsilane, N,N-dimethylaminotrimethylsilane, hexamethyldisiloxane, N-trimethylsilylimidazole, bis(trimethylsilyl)acetamide, bis(trimethylsilyl)trifluoroacetamide, bis(trimethylsilyl) ) Urea, 2-trimethylsiloxy-2
-Penten-4-one, trimethylsilylacetate, trimethylsilyl-NSN'-diphenylurea, 3
-trimethylsilyl-2-oxazolidinone, bis(trimethylsiloxy)dimethylsilane, and the like.
本発明において用いられる疎水性シリカは、前記した方
法で得られるが、既に市販されている疎水性シリカをも
ってこれに代えることができる．市販品の疎水性シリカ
としては、ｎ−オクチルトリメトキシシランで表面処理
された＾ＥＲＯＳＩＬ Ｒ８０５（ Ｄ ｅｇｕｓｓａ
社製）、シリコンオイルで表面処理されたＡＥＲＯＳＩ
Ｌ Ｒ２０２ （Ｄｅｇｕｓｓａ社製）、ジメチルシリ
ル化剤で表面処理されたＡＥＲＯＳＩＬ Ｒ９７２、Ｒ
９７４、Ｒ９７６ （何れもＤ ｅｇｕｓｓａ社製）、
トリメチルシリル化剤で表面処理されたＡＥＲＯＳＩＬ
Ｒ８１１ＳＲ８１２ （何れもＤ ｅｇｕｓｓａ社製
）等を挙げることができ、それらは、それぞれ、１５０
±２０、８０±２０，１１０±２０、１７０±２０，２
５０±２５、１５０±２０、２００±２０ボ／ｇの比表
面積、５０、６５、４０、３５、３０、６０、６０の疎
水化度を有する疎水性ヒュームドシリ力である。又、そ
の他の疎水性シリカとしては、Ｃａｂ−０−Ｓｉｌ Ｎ
７０−ＴＳ（ＣＡＢＯＴ社製〉カアり、１００＋２０ｒ
ｒｒ／ｇ（７１比表面積を有し、有機珪素化合物で処理
されたものとして報告されている。The hydrophobic silica used in the present invention can be obtained by the method described above, but it can be replaced with hydrophobic silica that is already commercially available. Commercially available hydrophobic silica includes ^EROSIL R805 (Degussa) surface-treated with n-octyltrimethoxysilane.
manufactured by AEROSI, surface treated with silicone oil.
L R202 (manufactured by Degussa), AEROSIL R972 surface treated with dimethylsilylation agent, R
974, R976 (all manufactured by Degussa),
AEROSIL surface treated with trimethylsilylating agent
R811SR812 (all manufactured by Degussa), etc., each of which has a weight of 150
±20, 80±20, 110±20, 170±20,2
It is a hydrophobic fumed silicone with a specific surface area of 50±25, 150±20, 200±20 bo/g and a degree of hydrophobicity of 50, 65, 40, 35, 30, 60, 60. In addition, as other hydrophobic silica, Cab-0-Sil N
70-TS (manufactured by CABOT) Kaari, 100+20r
rr/g (with a specific surface area of 71 and is reported as treated with an organosilicon compound.
Ｏクラウンエーテル
クラウンエーテルはへテロ大環状化合物の総称として用
いられることもあるが、本発明においてはへテロ原子が
酸素のみである大環状ポリエーテルを意味し、具体的に
は、１５−クラウン−５、１８−クラウン−６、ジベン
ゾ−１８−クラウン−６、ベンゾー１５−クラウン−５
、ジベンゾ−２４−クラウン−８、ジベンゾ−３０−ク
ラウン−１０、トリベンゾ−１８−クラウン−６、ａｓ
ｙｒａ−ジベンゾ−２２−クラウン−６、ジベンゾーｌ
４−クラウン−４、ジシクロへキシル−１８−クラウン
−６、ジシクロへキシル−２４−クラウン−８、シクロ
ヘキシル−１２−クラウン−４、１．２−デカリルー１
５−クラウン−５、１．２−ナフトー１５−クラウン−
５、３．４．５−ナフチル−１６−クラウン−５、１．
２−メチルベンゾー１８−クラウン−６、１．２−メチ
ルベンゾー５．６−メチルベンゾー１８−クラウン−６
、Ｌ２−ｔｅｒｔ−プチルーｌ８−クラウン−６、１．
２−ビニルベン’／’ − １５−クラウン−５、１．
２−ビニルベンゾー１８−クラウン−６、Ｌ２−ｔｅｒ
ｔブチルシクロへキシル−１８−クラウン−６、ａｓｙ
ｍ−シベンゾ−２２−クラウン−６、１．２−ベンゾー
１．４−ベンゾー５−オキシゲン−２０−クラウン−７
等である。Crown ether is sometimes used as a general term for hetero macrocyclic compounds, but in the present invention it refers to macrocyclic polyethers in which the only hetero atom is oxygen, and specifically, 15-crown- 5, 18-crown-6, dibenzo-18-crown-6, benzo-15-crown-5
, dibenzo-24-crown-8, dibenzo-30-crown-10, tribenzo-18-crown-6, as
yra-dibenzo-22-crown-6, dibenzo l
4-crown-4, dicyclohexyl-18-crown-6, dicyclohexyl-24-crown-8, cyclohexyl-12-crown-4, 1,2-decarylu 1
5-crown-5, 1.2-naphtho 15-crown-
5,3.4.5-naphthyl-16-crown-5,1.
2-methylbenzo18-crown-6, 1,2-methylbenzo5.6-methylbenzo18-crown-6
, L2-tert-petitrou l8-crown-6, 1.
2-vinylben'/'-15-crown-5, 1.
2-vinylbenzo 18-crown-6, L2-ter
t-butylcyclohexyl-18-crown-6, asy
m-cybenzo-22-crown-6, 1,2-benzo1,4-benzo5-oxygen-20-crown-7
etc.
Ｏポリアルヰレンオキサイド
ポリアルキレンオキサイドとは、エチレンオキサイド、
プロピレンオキサイド、プチレンオキサイド、トリメチ
レンオキサイド、テトラメチレンオキサイド（テトラヒ
ドロフラン） 、１．３−ジオキソラン、トリオキサン
、テトラオキサン等のアルレンオヰサイド及びアルキレ
ン基の水素がハロゲン原子、水酸基、フェニル基等で置
換されたエピクロルヒドリン、エビブロモヒドリン、グ
リシドール、スチレンオキサイド等の化合物の１種又は
２種以上を主成分とする重合体を意味しホルムアルデヒ
ド、アセトアルデヒド、グリセリン等の化合物を主威分
とする重合体をも包含するものである。O Polyalkylene oxide Polyalkylene oxide is ethylene oxide,
Propylene oxide, butylene oxide, trimethylene oxide, tetramethylene oxide (tetrahydrofuran), 1,3-dioxolane, trioxane, tetraoxane and other allene oxides and alkylene group hydrogens are replaced with halogen atoms, hydroxyl groups, phenyl groups, etc. It refers to a polymer whose main component is one or more of the following compounds, such as epichlorohydrin, shrimp bromohydrin, glycidol, and styrene oxide. It also includes.
本発明に使用されるこれらの重合体の重合度として２以
上である必要があり、好ましくは４〜３０００程度であ
るが、場合によっては、重合度が１００００まで或いは
それ以上のものも使用し得るものがあるのは勿論である
．また分子量としては重合度に関連するものであるが４
００以上１００万以下のものが好ましく、ｔｏｏｏ以上
１００００以下のものがより好ましい。重合度が１のも
の及び小さいもの（分子量についても同じ）はセットタ
イムを促進する効果が小さく、発明が目的とする性能を
有する組威物を得ることが難しい．また重合度が１００
００をはるかに超えるような分子量が大きいものの場合
は、２−シアノアクリレ−トとの相客性が低下する傾向
にあり、それらに溶解させて、均一な組威物とすること
が困難となる．重合度が２以上の場合、何故セットタイ
ムを促進させる効果を有するのかその理由は明らかでな
いが、鎖状のポリアルキレンオキサイド中の酸素分子が
金属などと配位するためと推察される．また、アルキレ
ン基の炭素数が２〜６の範囲にあるものが、セットタイ
ムを促進させる効果にす゛ぐれており、本発明にとり好
ましいものであり、そのなかでもエチレン、ブロビレン
、イソプロピレン、テトラメチレン又はこれらの組み合
せからなるものが好ましく、特にプロピレン、テトラメ
チレン又はこれらの組み合せからなるものが好ましい．
本発明に用いられるポリアルキレンオキサイドの具体例
としては、次の様なものがあげられる．ジエチレングリ
コール、トリエチレングリコール、テトラエチレングリ
コール、ポリエチレングリコール、ボリプロビレングリ
コール、ボリ１，３一プロピレングリコール、ポリトリ
メチレンオキシド、ポリテトラメチレンオキシド、ポリ
エビクロルヒドリン、ボリ３．３−ビス（クロロメチル
）プチレンオキサイド、ポリテトラメチレンエーテルグ
リコール、ポリ１．３−ジオキソラン、ポリ２．２−ビ
ス（クロロメチル）プロピレンオキサイド、エチレンオ
キサイドープロピレンオキサイドブロックボリマー、ジ
グリセリン、トリグリセリン、テトラグリセリン等のポ
リグリセリン、ホルムアルデヒド縮合体、アセトアルデ
ヒド縮合体、トリオキサン重合体などである．またポリ
エーテル型ウレタン硬化用ボリオールとして市販されて
いる各種のポリアルキレンオキサイドも本発明に使用可
能である．
Ｏポリアルキレンオキサイドの誘導体
本発明におけるポリアルキレンオキサイドの誘導体とは
上記ポリアルキレンオキサイドと酸とのエステルおよび
ヒドロキシ基含有化合物とのエーテルに代表されるもの
であり、それらが好ましいものであるが、それらに特に
限定されるわけでなく、分子末端に種々の置換基を有し
ているもの、ポリアルキレンオキサイドの内部に他の結
合部を有しているもの等分子内部にポリアルキレンオキ
サイド構造を有するものであれば本発明の目的とする効
果を奏し得る．エステルを構戒しうる酸としては酢酸、
ブロピオン酸、酪酸、イソ酪酸、ピバリン酸、ペンタノ
イック酸、ｎ−ヘキサノイツク酸、２−メチルーペンタ
ノイック酸、ｔ−プチル酢酸、ｎ−ヘブタノイック酸、
ｎ−オクタノインク酸、ｎ−デカノイック酸、ラウリン
酸、パルξチン酸、ステアリン酸、オレイン酸、シクロ
ヘキシルカルボン酸、シクロベンチルカルボン酸、シク
ロプロビルカルボン酸、アクリル酸、メタクリル酸、マ
レイン酸、イタコン酸、ナフテン酸、安息香酸、β−ナ
フチルカルボン酸、ｐ一トルエンカルボン酸、フランカ
ルボン酸、ｐ−クロル安息香酸、モノクロル酢酸、シア
ノ酢酸、グリコール酸、乳酸、フエニルオキシブロビオ
ン酸、コハク酸、グルタル酸、アジビン酸、セバチン酸
、ブタンテトラカルボン酸、アコニット酸、プロパン−
１．２．３−トリカルボン酸、クエン酸、オルソフタル
酸、イソフタル酸、トリメリット酸などの酸を挙げるこ
とができる。The degree of polymerization of these polymers used in the present invention must be 2 or more, preferably about 4 to 3,000, but in some cases, polymers with a degree of polymerization of up to 10,000 or more may be used. Of course there are things. In addition, the molecular weight is related to the degree of polymerization, but 4
00 or more and 1,000,000 or less are preferable, and too0 or more and 10,000 or less are more preferable. Those with a polymerization degree of 1 and those with a small molecular weight (the same applies to molecular weight) have a small effect on accelerating set time, and it is difficult to obtain a composition having the performance aimed at by the invention. Also, the degree of polymerization is 100
If the molecular weight is large, far exceeding 0.00, the compatibility with 2-cyanoacrylate tends to decrease, making it difficult to dissolve them into a uniform composition. The reason why it has the effect of accelerating set time when the degree of polymerization is 2 or more is not clear, but it is presumed that it is because the oxygen molecules in the chain polyalkylene oxide coordinate with metals and the like. In addition, alkylene groups having carbon numbers in the range of 2 to 6 are excellent in the effect of accelerating set time and are preferable for the present invention. Among them, ethylene, brobylene, isopropylene, and tetramethylene are preferable. Or a combination thereof is preferred, and propylene, tetramethylene or a combination thereof is particularly preferred. Specific examples of polyalkylene oxides used in the present invention include the following. Diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol, poly-1,3-propylene glycol, polytrimethylene oxide, polytetramethylene oxide, polyevichlorohydrin, poly-3,3-bis(chloro methyl) butylene oxide, polytetramethylene ether glycol, poly 1,3-dioxolane, poly 2,2-bis(chloromethyl)propylene oxide, ethylene oxide-propylene oxide block polymer, diglycerin, triglycerin, tetraglycerin, etc. Polyglycerin, formaldehyde condensate, acetaldehyde condensate, trioxane polymer, etc. Various polyalkylene oxides commercially available as polyether-type polyols for curing urethane can also be used in the present invention. O Derivatives of polyalkylene oxide The derivatives of polyalkylene oxide in the present invention are represented by esters of the above-mentioned polyalkylene oxides and acids and ethers of hydroxy group-containing compounds, and these are preferred. It is not particularly limited to, but those having a polyalkylene oxide structure inside the molecule, such as those having various substituents at the end of the molecule, and those having other bonding parts inside the polyalkylene oxide. If so, the desired effect of the present invention can be achieved. Acids that can contain esters include acetic acid,
Bropionic acid, butyric acid, isobutyric acid, pivalic acid, pentanoic acid, n-hexanoic acid, 2-methyl-pentanoic acid, t-butylacetic acid, n-hebutanoic acid,
n-octanoic acid, n-decanoic acid, lauric acid, paltic acid, stearic acid, oleic acid, cyclohexylcarboxylic acid, cyclobentylcarboxylic acid, cyclopropylcarboxylic acid, acrylic acid, methacrylic acid, maleic acid, itacon Acid, naphthenic acid, benzoic acid, β-naphthylcarboxylic acid, p-toluenecarboxylic acid, furancarboxylic acid, p-chlorobenzoic acid, monochloroacetic acid, cyanoacetic acid, glycolic acid, lactic acid, phenyloxybrobionic acid, succinic acid , glutaric acid, adivic acid, sebacic acid, butanetetracarboxylic acid, aconitic acid, propane-
Mention may be made of acids such as 1.2.3-tricarboxylic acid, citric acid, orthophthalic acid, isophthalic acid and trimellitic acid.
エーテルを構成しうるヒドロキシ基含有化合物としては
メタノール、エタノール、プロバノール、イソプロパノ
ール、ブタノール、イソプタノーノレ、ヘキサノール、
シクロヘキサノール、２−エチルオクタノール、デカノ
ール、ラウリルアルコール、セシルアルコール、ステア
リルアルコール、オレイルアルコール、フェノール、α
−ナフトール、β−ナフトール、クレゾール、ｔ−プチ
ルフェノール、オクチルフェノール、ノニルフェノール
、ｐ−クロロフェノール、レゾール、ビスフェノールＡ
１２−クロロエタノール、エチレンシアンヒドリン、ト
リフルオロエタノール、ベンジルアルコール、１．４−
ブタンジオール、１．６−ヘキサンジオーノレ、グリセ
リン、ソルビトール、水素化ビスフェノールＡ、トリメ
チロールプロパンなどのヒドロキシ基含有化合物等をあ
げることができる．
ポリアルキレンオキサイド誘導体としてのエステル又は
エーテルの具体例としては、ジエチレングリコールモノ
アルキルエーテル（アルキルとしては例えばメチル、エ
チル、プロビル、プチルなと）、ジエチレングリコール
ジアルキルエーテル（アルキルとしては例えばメチル、
エチル、プロビル、ブチルなと）、ポリエチレングリコ
ールモノアルキルエーテル（アルキルとしては例えばメ
チル、エチル、プロビル、ラウリル、セシル、ステアリ
ル、オレイルなど）、ボリプロビレングリコールモノア
ルキルエーテル（アルキルとしては例えばメチル、エチ
ル、ラウリル、プロビル、ステアリル、セシル、オレイ
ル、パーフルオロアルキルなど）、ポリエチレングリコ
ールモノアリールエーテル（アリールとしては例えば、
オクチルフエニル、ノニルフエニルなど）、ポリエチレ
ングリコールジアルキルエーテル、ポリエチレングリコ
ールモノアルキルエステル（例えば、アセテート、トリ
フルオロアセテート、ラウレート、ステアレート、オレ
エート、メタクリレートなどのエステル）、ポリエチレ
ングリコールジエステル、ポリプロピレングリコールジ
エステル、ビスフェノールＡ−ポリアルキレンオキサイ
ド付加物（アルキレンとしてたとえばエチレン、プロピ
レン等以下同じ）、水素化ビスフェノールＡ−ポリアル
キレンオキサイド付加物、トリメチロールブロパンーボ
リアルキレンオキサイド付加物、グリセリンーボリアル
キレンオキサイド付加物、ポリオキシエチレンソルビク
ンエステル、テトラオレイン酸−ボリオキシエチレンソ
ルビット、アジピン酸−ボリアルキレンオキサイド付加
物、トリメリット酸一ポリアルキレンオキサイド付加物
、イソシアネート化合物一ボリアルキレンオキサイド付
加物、リン酸一ボリアルキレンオキサイド付加物、ケイ
酸一ポリアルキレンオキサイド付加物、（ポリオキシア
ルキレン）ポリシラノレート、（ポリオキシアルキレン
）ポリエステル、（ボリオキシアルキレン）ポリホスフ
エートなどである．○その他の添加物
本発明の組或物には上記の成分の他に、通常２ーシアノ
アクリル酸エステル系の瞬間接着剤に配合される種々の
添加物、例えばアニオン重合防止剤、ラジカル重合防止
剤、増粘剤、可塑剤、染料、顔料、香料等を同様に配合
することができる．アニオン重合防止剤とは組或物中の
水分等によるアニオン重合を防止するためのものであり
、４体的には、Ｓ Ｏ ２、Ｓ○，、Ｎｏ，Ｎｏｗ、Ｈ
ＣＩ、Ｈ３ＰＯ．、酸性リン酸エステル、芳香族スルホ
ン酸、アルキルスルホン酸、プロパンサルトン、トリフ
ルオロメタンスルホン酸、パーフルオロアルキルカルボ
ン酸等が挙げられる。好ましい配合１は１〜１ ０ ０
０ｐｐｍ ，より好ましくは５〜１００ｐｐｍである
。Hydroxy group-containing compounds that can constitute ether include methanol, ethanol, propanol, isopropanol, butanol, isoptanol, hexanol,
Cyclohexanol, 2-ethyl octanol, decanol, lauryl alcohol, cecyl alcohol, stearyl alcohol, oleyl alcohol, phenol, α
- Naphthol, β-naphthol, cresol, t-butylphenol, octylphenol, nonylphenol, p-chlorophenol, resol, bisphenol A
12-Chloroethanol, ethylene cyanohydrin, trifluoroethanol, benzyl alcohol, 1.4-
Examples include hydroxy group-containing compounds such as butanediol, 1,6-hexanediol, glycerin, sorbitol, hydrogenated bisphenol A, and trimethylolpropane. Specific examples of esters or ethers as polyalkylene oxide derivatives include diethylene glycol monoalkyl ether (alkyl examples include methyl, ethyl, proyl, and butyl), diethylene glycol dialkyl ether (alkyl examples include methyl,
ethyl, proyl, butyl), polyethylene glycol monoalkyl ether (alkyl examples include methyl, ethyl, proyl, lauryl, ceyl, stearyl, oleyl, etc.), polypropylene glycol monoalkyl ether (alkyl examples include methyl, ethyl, etc.) , lauryl, proyl, stearyl, ceyl, oleyl, perfluoroalkyl, etc.), polyethylene glycol monoaryl ether (aryl includes, for example,
octylphenyl, nonylphenyl, etc.), polyethylene glycol dialkyl ether, polyethylene glycol monoalkyl ester (e.g., ester of acetate, trifluoroacetate, laurate, stearate, oleate, methacrylate, etc.), polyethylene glycol diester, polypropylene glycol diester, bisphenol A -Polyalkylene oxide adduct (alkylene is, for example, ethylene, propylene, etc.), hydrogenated bisphenol A-polyalkylene oxide adduct, trimethylolpropane-borealkylene oxide adduct, glycerin-borealkylene oxide adduct, polyoxyethylene Sorbikune ester, tetraoleic acid-bolyoxyethylene sorbitol, adipic acid-borialkylene oxide adduct, trimellitic acid monopolyalkylene oxide adduct, isocyanate compound monoborealkylene oxide adduct, phosphoric acid monoborealkylene oxide adduct, These include silicic acid monopolyalkylene oxide adducts, (polyoxyalkylene) polysilanolates, (polyoxyalkylene) polyesters, and (bolyoxyalkylene) polyphosphates. ○Other additives In addition to the above-mentioned components, the composition of the present invention contains various additives that are usually added to 2-cyanoacrylic acid ester instant adhesives, such as anionic polymerization inhibitors, radical polymerization inhibitors, Thickeners, plasticizers, dyes, pigments, fragrances, etc. can be added in the same way. Anionic polymerization inhibitors are used to prevent anionic polymerization caused by moisture, etc. in a composition, and include SO 2, SO,, No, Now, and H.
CI, H3PO. , acidic phosphoric acid ester, aromatic sulfonic acid, alkyl sulfonic acid, propane sultone, trifluoromethanesulfonic acid, perfluoroalkyl carboxylic acid, and the like. Preferred formulation 1 is 1 to 100
0 ppm, more preferably 5 to 100 ppm.
ラジカル重合防止剤とは、主として貯蔵中にあたる光な
どによって生じるラジカル重合や嫌気竹重合を防止する
目的で添加されるものであり、舅体的には、フェノール
、クレゾール、ハイドロキノン、ハイドロキノンモノメ
チルエーテル、カテコール、ピロガロール等が挙げられ
る。好ましレ配合量は１０〜１００００ｐｐｍ、より好
ましく−ｌＯＯ〜５０００ｐｐｍである．
増粘剤は接着剤の粘度を調整する目的で添加されるが、
疎水性シリカの分散安定性を向上させる効果も有する。Radical polymerization inhibitors are added for the purpose of preventing radical polymerization and anaerobic polymerization that occur mainly due to light exposure during storage, and include phenol, cresol, hydroquinone, hydroquinone monomethyl ether, and catechol. , pyrogallol and the like. The preferred amount is 10 to 10,000 ppm, more preferably -1OO to 5,000 ppm. Thickeners are added to adjust the viscosity of adhesives, but
It also has the effect of improving the dispersion stability of hydrophobic silica.
具体的には、ポリメチルメククリレート、ポリメチルア
クリレート、ポリビニルアセテート、セルロースエステ
ル等が挙げられる。Specific examples include polymethyl meccrylate, polymethyl acrylate, polyvinyl acetate, cellulose ester, and the like.
配合量は通常１〜１０重量％である。The blending amount is usually 1 to 10% by weight.
また、２−シアノアクリル酸エステル系の瞬間接着剤に
おいて衝撃接着強さや剥離接着強さを向上させるために
使用されるカルボン酸、ジカルボン酸やその無水物及び
アクリルゴム、ウレタンゴム等のエラストマーを同様に
配合することができる。In addition, we also use carboxylic acids, dicarboxylic acids, their anhydrides, and elastomers such as acrylic rubber and urethane rubber, which are used to improve the impact adhesive strength and peel adhesive strength of 2-cyanoacrylic acid ester-based instant adhesives. It can be blended with.
○配合割合
本発明にとり、２−シアノ−２．４−ペンタジエン酸エ
ステルの２−シアノアクリル酸エステルへの配合割合は
１０重量％以上かつ５０重量％以下であることが好まし
い。１０重量％より少ないと十分な耐水性が得られず、
一方、５０重量％を超えると十分な速硬化性と接着強さ
が得られ難くなる。Blending ratio In the present invention, the blending ratio of 2-cyano-2,4-pentadienoic acid ester to 2-cyanoacrylic acid ester is preferably 10% by weight or more and 50% by weight or less. If it is less than 10% by weight, sufficient water resistance cannot be obtained;
On the other hand, if it exceeds 50% by weight, it becomes difficult to obtain sufficient fast curing properties and adhesive strength.
疎水性シリカ及びクラウンエーテル、ポリアルキレンオ
キサイドまたはその誘導体の好ましい配合割合はその種
類によっても異なり、特に限定されないが、一般的には
２−シアノアクリル酸エステル、２−シアノ−２．４−
ペンタジエン酸エステルの混合物に対して、好ましくは
、それぞれｌ〜３０重量％及び０．００１〜１０重景％
である．さらに好ましくは、それぞれ３〜２０重量％及
び０． ０ ０ ３〜１重景％である。疎水性シリカの
配合割合が、１重量％より少ないと十分な耐水性、接着
強さが得られず、一方、３０重量％を超えると速硬化性
接着強さ、貯蔵安定性が低下する傾向にある。また、ク
ラウンエーテル、ポリアルキレンオキサイドまたはその
誘導体の配合割合が０．００１重量％より少ないと十分
な速硬化性、接着強さが得られず、一方、１０重量％を
超えると速硬化性が余り大きくならない割に接着強さ、
貯蔵安定性が著しく低下する傾向にある。The preferred blending ratio of hydrophobic silica, crown ether, polyalkylene oxide or its derivatives varies depending on the type and is not particularly limited, but generally 2-cyanoacrylic acid ester, 2-cyano-2.4-
Based on the mixture of pentadienoic acid esters, preferably 1 to 30% by weight and 0.001 to 10% by weight, respectively.
It is. More preferably, 3-20% by weight and 0.0% by weight, respectively. 0 0 3 to 1% of heavy visibility. If the blending ratio of hydrophobic silica is less than 1% by weight, sufficient water resistance and adhesive strength cannot be obtained, while if it exceeds 30% by weight, fast-curing adhesive strength and storage stability tend to decrease. be. In addition, if the blending ratio of crown ether, polyalkylene oxide, or its derivative is less than 0.001% by weight, sufficient fast curing properties and adhesive strength cannot be obtained, while if it exceeds 10% by weight, fast curing properties are insufficient. Adhesive strength even though it is not large,
Storage stability tends to decrease significantly.
「作用」
本発明の瞬間接着剤組戒物は、種々の材料の接着におい
て優れた速硬化性と接着強さを有する上に、従来の瞬間
接着剤では考えられなかったような高度な耐水性を有す
るものであり、瞬間接着剤の用途を大きく広げるもので
ある。"Function" The instant adhesive composition of the present invention not only has excellent fast curing properties and adhesive strength when adhering various materials, but also has a high degree of water resistance that was unimaginable with conventional instant adhesives. This greatly expands the applications of instant adhesives.
このような作用が発現する機構ははっきりしていないが
、主として２−シアノ−２．４−ペンタジエン酸エステ
ルが高分子鎖中に導入されることによる加水分解性の低
下と疎水性シリヵの配合による吸水性の低下が高度な耐
水性の発現に寄与しているもの・と考えられる。しかし
、２−シアノ〜２．４−ペンタジエン酸エステル等の１
．１−ジＷ換ジェンの配合割合が２−シアノアクリル酸
エステルに対し５０重量％以下では耐水性が低いことは
特公昭６２−２８８３５で明らかであり、本発明のごと
き作用の発現は全く予想できないものである。The mechanism by which this effect occurs is not clear, but it is mainly due to the reduction in hydrolyzability due to the introduction of 2-cyano-2,4-pentadienoic acid ester into the polymer chain and the addition of hydrophobic silica. It is thought that the decrease in water absorption contributes to the development of high water resistance. However, 1 such as 2-cyano-2,4-pentadienoic acid ester
．． It is clear from Japanese Patent Publication No. 62-28835 that water resistance is low when the blending ratio of 1-diW diene is less than 50% by weight relative to 2-cyanoacrylic acid ester, and the development of the effect of the present invention cannot be expected at all. It is something.
「実施例及び比較例」
実施例１〜１４
本発明に従って表１に示された１４種の組成物を調合し
た。表中における安定剤、クラウンエーテル他の配合量
は２−シアノアクリル酸エステルと２−シアノ−２．４
−ペンタジエン酸エステルの混合物に対する配合割合で
あり、また、増粘剤、疎水性シリカの配合量はｆｆｉｆ
ｆｉ％である。このものを用いて２３℃／６０％ＲＨの
ふん囲気下でのステ：レスのセットタイムを測定した結
果を表１に示したが、１０〜３０秒と速硬化性であった
．また、２３゜Ｃ／６０％ＲＨのふん囲気下で接着した
ステンレスの引張り剪断試験片の常態での接着強さと、
５０゜Ｃ温水に１６８時間浸漬した後の接着強さを測定
した。結果を表１に示したが、いずれも高い接着強さが
得られた。さらに、アルミチューブにＭｉ底物３ｇを充
填し、６０℃加熱下での安定性試験を行ったところ、い
ずれも２０日以上変化がなく実用的に十分な安定性があ
ることが確かめられた。また、耐水性についてより実用
的な評価を行うために、実施例ｌのＭｉ戒物を用いてク
ロムメッキとおしの引張り剪断接着強さ、クロムメッキ
とＥＰＤＭとの１８０゛剥離接着強さ、及びガラスとＥ
ＰＤＭとの１８０゜剥離接着強さについてステンレスと
同様に耐水試験を行った。結果を表２に示したが、いず
れも耐水性が良好であった。"Examples and Comparative Examples" Examples 1-14 Fourteen compositions shown in Table 1 were prepared according to the present invention. The amounts of stabilizers, crown ether, etc. in the table are 2-cyanoacrylic acid ester and 2-cyano-2.4
- The blending ratio of the pentadienoate ester to the mixture, and the blending amount of the thickener and hydrophobic silica are ffif
fi%. Table 1 shows the results of measuring the setting time of stainless steel under an atmosphere of 23° C./60% RH using this product, and it was found to be fast curing at 10 to 30 seconds. In addition, the adhesive strength under normal conditions of stainless steel tensile shear test pieces bonded under ambient air at 23 ° C / 60% RH,
The adhesive strength was measured after being immersed in 50°C hot water for 168 hours. The results are shown in Table 1, and high adhesive strength was obtained in all cases. Furthermore, when an aluminum tube was filled with 3 g of Mi bottom material and a stability test was conducted under heating at 60° C., it was confirmed that there was no change for more than 20 days, and that there was sufficient stability for practical use. In addition, in order to conduct a more practical evaluation of water resistance, we used the Mi material of Example 1 to measure the tensile shear adhesion strength between the chrome plating and the EPDM, the 180° peel adhesion strength between the chrome plating and the EPDM, and the glass and E
A water resistance test was conducted in the same manner as stainless steel for 180° peel adhesion strength with PDM. The results are shown in Table 2, and all had good water resistance.
一一一（以 下 余 白）一一一
比較例１
２−シアノアクリル酸エチルを用いて実施例１と同様の
試験を行った結果を前記表２及び表３に示した。常態接
着強さは良好であるが耐水性はほとんど無かった。111 (hereinafter referred to as the margin) 111 Comparative Example 1 The same test as in Example 1 was conducted using ethyl 2-cyanoacrylate, and the results are shown in Tables 2 and 3 above. Although the normal adhesive strength was good, there was almost no water resistance.
比較例２
２−シアノアクリル酸エチルと２−シアノ−２，４−ペ
ンタ、ジエン酸メチルを４０／６０の比で配合した組或
物を用いて実施例１と同様の試験を行った結果を前記表
２及び表３に示した。セットタイムが遅く、また、種々
材料における常態接着強さも低かった．ステンレス、ク
ロムメッキの接着における耐水性はかなり良好であった
が、クロムメッキとＥＰＤＭ、ガラスとＥＰＤＭの接着
では常態接着強さが低い上に耐水性も低めであった。Comparative Example 2 The same test as in Example 1 was conducted using a composition containing ethyl 2-cyanoacrylate and methyl 2-cyano-2,4-penta,dienoate in a ratio of 40/60. It is shown in Tables 2 and 3 above. The set time was slow, and the normal adhesive strength for various materials was also low. The water resistance of adhesion between stainless steel and chrome plating was quite good, but the adhesion between chrome plating and EPDM, and between glass and EPDM had low normal adhesive strength and water resistance.
一一一（以 下 余 白）一一一
比較例３〜８
２−シアノアクリル酸エチルと２−シアノ−２．４−ペ
ンタジエン酸メチルをもとにして本発明外の６種の組成
物を配合し、実施例２〜１４と同様の試験を行った。結
果を前記表３に示したが、速硬化性、常態接着強さ、耐
水性のいずれかに問題があり、本発明が目的とする性能
は得られなかった。111 (hereinafter referred to as blank) 111 Comparative Examples 3 to 8 Six types of compositions other than the present invention were prepared based on ethyl 2-cyanoacrylate and methyl 2-cyano-2,4-pentadienoate. The same tests as in Examples 2 to 14 were conducted. The results are shown in Table 3 above, but there were problems with either quick curing properties, normal adhesive strength, or water resistance, and the performance aimed at by the present invention could not be obtained.
（ハ）発明の効果
本発明の瞬間接着剤組成物は、金属、プラスチック、ゴ
ム、セラミック、木材等の種々材料において優れた速硬
化性と接着強さを有し、かつ高度な耐水性を有する瞬間
接着剤を提供するものであり、該瞬間接着剤は従来のも
のよりさらに多くの用途において幅広く利用され、各種
産業界、医療分野、レジャー分野、さらには一般家庭に
おける接着において貢献するところ大なるものである。(c) Effects of the invention The instant adhesive composition of the present invention has excellent fast curing properties and adhesive strength on various materials such as metals, plastics, rubber, ceramics, and wood, and has a high degree of water resistance. This instant adhesive is used in a wider range of applications than conventional adhesives, making a great contribution to various industries, the medical field, the leisure field, and even in general household adhesives. It is something.
Claims (1)
成物。 （１）２−シアノアクリル酸エステル （２）２−シアノ−２，４−ペンタジエン酸エステル（
３）疎水性シリカ （４）クラウンエーテル、ポリアルキレンオキサイドま
たはその誘導体[Claims] 1. An instant adhesive composition comprising the following four components. (1) 2-cyanoacrylic acid ester (2) 2-cyano-2,4-pentadienoic acid ester (
3) Hydrophobic silica (4) Crown ether, polyalkylene oxide or its derivative
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30723989A JP2671528B2 (en) | 1989-11-27 | 1989-11-27 | Instant adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30723989A JP2671528B2 (en) | 1989-11-27 | 1989-11-27 | Instant adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03167279A true JPH03167279A (en) | 1991-07-19 |
| JP2671528B2 JP2671528B2 (en) | 1997-10-29 |
Family
ID=17966711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30723989A Expired - Fee Related JP2671528B2 (en) | 1989-11-27 | 1989-11-27 | Instant adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2671528B2 (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05331422A (en) * | 1992-05-29 | 1993-12-14 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| JPH05331423A (en) * | 1992-05-29 | 1993-12-14 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| JPH06122853A (en) * | 1992-10-09 | 1994-05-06 | Ohara Parajiumu Kagaku Kk | Adhesive composition |
| US5386047A (en) * | 1994-03-11 | 1995-01-31 | Loctite Corporation | Di-α-cyanopentadienoate disiloxane compounds for use in adhesives |
| WO1998014526A1 (en) * | 1996-09-30 | 1998-04-09 | Henkel Kommanditgesellschaft Auf Aktien | Cyanoacrylate adhesive |
| US6323275B2 (en) | 1992-05-28 | 2001-11-27 | Toagosei Co., Ltd. | Cyanoacrylate adhesive composition |
| US6547985B1 (en) * | 1999-04-07 | 2003-04-15 | Togosei Co., Ltd. | Composition of 2-cyanoacrylate, Lewis acid metal salt and clathrate |
| WO2010074095A1 (en) | 2008-12-25 | 2010-07-01 | 東亞合成株式会社 | Adhesive composition |
| JP2013135070A (en) * | 2011-12-26 | 2013-07-08 | Jsr Corp | Pattern forming method and metal pattern |
| WO2014042082A1 (en) | 2012-09-11 | 2014-03-20 | 東亞合成株式会社 | 2-cyanoacrylate-based adhesive composition |
| WO2014091966A1 (en) | 2012-12-14 | 2014-06-19 | 東亞合成株式会社 | Adhesive composition |
| WO2015033738A1 (en) | 2013-09-03 | 2015-03-12 | 東亞合成株式会社 | Adhesive composition |
| WO2015083725A1 (en) | 2013-12-05 | 2015-06-11 | 東亞合成株式会社 | Reinforcement method for three-dimensional shaped object |
| WO2017014124A1 (en) * | 2015-07-21 | 2017-01-26 | 東亞合成株式会社 | Curable composition |
| US9994662B2 (en) | 2014-12-12 | 2018-06-12 | Toagosei Co., Ltd. | Two-part curable composition |
| US10487244B2 (en) | 2014-10-15 | 2019-11-26 | Toagosei Co., Ltd. | 2-cyanoacrylate composition having magnetism |
| US10647888B2 (en) | 2015-02-18 | 2020-05-12 | Toagosei Co., Ltd. | 2-cyanoacrylate adhesive composition |
| CN114395334A (en) * | 2022-03-15 | 2022-04-26 | 宁波百仕高联合工业有限公司 | Preparation method of high-water-resistance instant adhesive |
-
1989
- 1989-11-27 JP JP30723989A patent/JP2671528B2/en not_active Expired - Fee Related
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6323275B2 (en) | 1992-05-28 | 2001-11-27 | Toagosei Co., Ltd. | Cyanoacrylate adhesive composition |
| JPH05331422A (en) * | 1992-05-29 | 1993-12-14 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| JPH05331423A (en) * | 1992-05-29 | 1993-12-14 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| JPH06122853A (en) * | 1992-10-09 | 1994-05-06 | Ohara Parajiumu Kagaku Kk | Adhesive composition |
| US5386047A (en) * | 1994-03-11 | 1995-01-31 | Loctite Corporation | Di-α-cyanopentadienoate disiloxane compounds for use in adhesives |
| WO1998014526A1 (en) * | 1996-09-30 | 1998-04-09 | Henkel Kommanditgesellschaft Auf Aktien | Cyanoacrylate adhesive |
| US6201088B1 (en) | 1996-09-30 | 2001-03-13 | Henkel Kommanditgesellschaft Auf Aktien | Cyanoacrylate adhesive |
| US6547985B1 (en) * | 1999-04-07 | 2003-04-15 | Togosei Co., Ltd. | Composition of 2-cyanoacrylate, Lewis acid metal salt and clathrate |
| US6830704B2 (en) | 1999-04-07 | 2004-12-14 | Toagosei Co., Ltd. | Composition of 2-cyanoacrylate, lewis acid metal salt and clathrate |
| US8541495B2 (en) | 2008-12-25 | 2013-09-24 | Toagosei Co., Ltd. | Adhesive composition |
| KR20110097783A (en) * | 2008-12-25 | 2011-08-31 | 도아고세이가부시키가이샤 | Adhesive composition |
| CN102264852A (en) * | 2008-12-25 | 2011-11-30 | 东亚合成株式会社 | Adhesive composition |
| JP5267571B2 (en) * | 2008-12-25 | 2013-08-21 | 東亞合成株式会社 | Adhesive composition |
| WO2010074095A1 (en) | 2008-12-25 | 2010-07-01 | 東亞合成株式会社 | Adhesive composition |
| JP2013135070A (en) * | 2011-12-26 | 2013-07-08 | Jsr Corp | Pattern forming method and metal pattern |
| WO2014042082A1 (en) | 2012-09-11 | 2014-03-20 | 東亞合成株式会社 | 2-cyanoacrylate-based adhesive composition |
| WO2014091966A1 (en) | 2012-12-14 | 2014-06-19 | 東亞合成株式会社 | Adhesive composition |
| WO2015033738A1 (en) | 2013-09-03 | 2015-03-12 | 東亞合成株式会社 | Adhesive composition |
| WO2015083725A1 (en) | 2013-12-05 | 2015-06-11 | 東亞合成株式会社 | Reinforcement method for three-dimensional shaped object |
| US10487244B2 (en) | 2014-10-15 | 2019-11-26 | Toagosei Co., Ltd. | 2-cyanoacrylate composition having magnetism |
| US9994662B2 (en) | 2014-12-12 | 2018-06-12 | Toagosei Co., Ltd. | Two-part curable composition |
| US10647888B2 (en) | 2015-02-18 | 2020-05-12 | Toagosei Co., Ltd. | 2-cyanoacrylate adhesive composition |
| WO2017014124A1 (en) * | 2015-07-21 | 2017-01-26 | 東亞合成株式会社 | Curable composition |
| CN107849164A (en) * | 2015-07-21 | 2018-03-27 | 东亚合成株式会社 | Solidification compound |
| KR20180032590A (en) * | 2015-07-21 | 2018-03-30 | 도아고세이가부시키가이샤 | Curable composition |
| US10501565B2 (en) | 2015-07-21 | 2019-12-10 | Toagosei Co., Ltd. | Curable composition |
| CN114395334A (en) * | 2022-03-15 | 2022-04-26 | 宁波百仕高联合工业有限公司 | Preparation method of high-water-resistance instant adhesive |
| CN114395334B (en) * | 2022-03-15 | 2023-09-26 | 宁波百仕高联合工业有限公司 | Preparation method of high-water-resistance instant adhesive |
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| Publication number | Publication date |
|---|---|
| JP2671528B2 (en) | 1997-10-29 |
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