KR101687424B1 - 2액형 시아노아크릴레이트 접착제를 위한 활성화제 - Google Patents
2액형 시아노아크릴레이트 접착제를 위한 활성화제 Download PDFInfo
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- KR101687424B1 KR101687424B1 KR1020117011491A KR20117011491A KR101687424B1 KR 101687424 B1 KR101687424 B1 KR 101687424B1 KR 1020117011491 A KR1020117011491 A KR 1020117011491A KR 20117011491 A KR20117011491 A KR 20117011491A KR 101687424 B1 KR101687424 B1 KR 101687424B1
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- Prior art keywords
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- benzothiazole
- activator
- cyanoacrylate
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- 239000004830 Super Glue Substances 0.000 title claims description 18
- 239000012190 activator Substances 0.000 title description 93
- 239000000203 mixture Substances 0.000 claims abstract description 82
- -1 2-substituted benzothiazole Chemical class 0.000 claims abstract description 55
- 229920001651 Cyanoacrylate Polymers 0.000 claims abstract description 39
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims abstract description 37
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 15
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 claims description 12
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 12
- MJHNUUNSCNRGJE-UHFFFAOYSA-N trimethyl benzene-1,2,4-tricarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(C(=O)OC)=C1 MJHNUUNSCNRGJE-UHFFFAOYSA-N 0.000 claims description 8
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 claims description 6
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 claims description 6
- 239000001087 glyceryl triacetate Substances 0.000 claims description 6
- 235000013773 glyceryl triacetate Nutrition 0.000 claims description 6
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 claims description 6
- 229960002622 triacetin Drugs 0.000 claims description 6
- 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 claims description 5
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 claims description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 4
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005591 trimellitate group Chemical group 0.000 claims description 4
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 claims description 4
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- 229940014772 dimethyl sebacate Drugs 0.000 claims description 3
- 230000009977 dual effect Effects 0.000 claims description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 2
- YRTNMMLRBJMGJJ-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;hexanedioic acid Chemical compound OCC(C)(C)CO.OC(=O)CCCCC(O)=O YRTNMMLRBJMGJJ-UHFFFAOYSA-N 0.000 claims description 2
- LUNMJRJMSXZSLC-UHFFFAOYSA-N 2-cyclopropylethanol Chemical compound OCCC1CC1 LUNMJRJMSXZSLC-UHFFFAOYSA-N 0.000 claims description 2
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 claims description 2
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 claims description 2
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims description 2
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 claims description 2
- DJACTCNGCHPGOI-UHFFFAOYSA-N butyl 2-cyanoacetate Chemical compound CCCCOC(=O)CC#N DJACTCNGCHPGOI-UHFFFAOYSA-N 0.000 claims description 2
- 229940100539 dibutyl adipate Drugs 0.000 claims description 2
- 229960002380 dibutyl phthalate Drugs 0.000 claims description 2
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 claims description 2
- RLRMXWDXPLINPJ-UHFFFAOYSA-N dioctan-2-yl benzene-1,2-dicarboxylate Chemical compound CCCCCCC(C)OC(=O)C1=CC=CC=C1C(=O)OC(C)CCCCCC RLRMXWDXPLINPJ-UHFFFAOYSA-N 0.000 claims description 2
- RXJJVYBGRFLCOX-UHFFFAOYSA-N dioctyl pentanedioate Chemical compound CCCCCCCCOC(=O)CCCC(=O)OCCCCCCCC RXJJVYBGRFLCOX-UHFFFAOYSA-N 0.000 claims description 2
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 2
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 claims description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims 4
- DEBGNTMWOUWECO-UHFFFAOYSA-N 2-o-acetyl 1-o,3-o-diethyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(O)(C(=O)OC(C)=O)CC(=O)OCC DEBGNTMWOUWECO-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 claims 1
- 229940031954 dibutyl sebacate Drugs 0.000 claims 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 abstract description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 18
- 125000000217 alkyl group Chemical group 0.000 abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 abstract description 11
- 125000004001 thioalkyl group Chemical group 0.000 abstract description 10
- 150000001336 alkenes Chemical class 0.000 abstract description 8
- 125000006177 alkyl benzyl group Chemical group 0.000 abstract description 8
- 150000001408 amides Chemical group 0.000 abstract description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 7
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 7
- 125000005189 alkyl hydroxy group Chemical group 0.000 abstract description 7
- 125000005309 thioalkoxy group Chemical group 0.000 abstract description 7
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 45
- 239000000853 adhesive Substances 0.000 description 42
- 230000001070 adhesive effect Effects 0.000 description 42
- 239000000758 substrate Substances 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 238000012360 testing method Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 230000032683 aging Effects 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- DROOTVOQFYXGLG-UHFFFAOYSA-N benzene;1,3-benzothiazole Chemical group C1=CC=CC=C1.C1=CC=C2SC=NC2=C1 DROOTVOQFYXGLG-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 125000001033 ether group Chemical group 0.000 description 6
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 5
- 239000005060 rubber Substances 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- 230000003213 activating effect Effects 0.000 description 4
- 125000005011 alkyl ether group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- FJDAAUABGSPSKH-UHFFFAOYSA-N s-(4-tert-butyl-1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound CC(C)(C)C1=CC=CC2=C1N=C(SN)S2 FJDAAUABGSPSKH-UHFFFAOYSA-N 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 3
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 3
- 238000006664 bond formation reaction Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- OUXMJRMYZCEVKO-UHFFFAOYSA-N 2-methylbenzo[e][1,3]benzothiazole Chemical compound C1=CC=C2C(N=C(S3)C)=C3C=CC2=C1 OUXMJRMYZCEVKO-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940125833 compound 23 Drugs 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000004862 thiobutyl group Chemical group 0.000 description 2
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- CYWHLOXWVAWMFO-UHFFFAOYSA-N 3-sulfanyl-1h-pyridine-2-thione Chemical compound SC1=CC=CN=C1S CYWHLOXWVAWMFO-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- SKYIQJWBDNSXRU-UHFFFAOYSA-N CCOCC(=O)OC(=O)CC(CC(=O)O)(C(=O)O)O Chemical compound CCOCC(=O)OC(=O)CC(CC(=O)O)(C(=O)O)O SKYIQJWBDNSXRU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical group FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- HCQHIEGYGGJLJU-UHFFFAOYSA-N didecyl hexanedioate Chemical compound CCCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCCC HCQHIEGYGGJLJU-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- WGARMULIELDQEH-UHFFFAOYSA-N n-cyclohexyl-1,3-benzothiazole-2-sulfinamide Chemical compound N=1C2=CC=CC=C2SC=1S(=O)NC1CCCCC1 WGARMULIELDQEH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/04—Homopolymers or copolymers of nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Packages (AREA)
- Packaging Of Annular Or Rod-Shaped Articles, Wearing Apparel, Cassettes, Or The Like (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| US10713708P | 2008-10-21 | 2008-10-21 | |
| US61/107,137 | 2008-10-21 | ||
| PCT/EP2009/063833 WO2010046412A1 (en) | 2008-10-21 | 2009-10-21 | Activators for two part cyanoacrylate adhesives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20110079731A KR20110079731A (ko) | 2011-07-07 |
| KR101687424B1 true KR101687424B1 (ko) | 2016-12-19 |
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| EP (1) | EP2346956B1 (enExample) |
| JP (1) | JP5785083B2 (enExample) |
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| HU (1) | HUE038460T2 (enExample) |
| MX (1) | MX336405B (enExample) |
| NO (1) | NO2346956T3 (enExample) |
| PL (1) | PL2346956T3 (enExample) |
| WO (1) | WO2010046412A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO2346956T3 (enExample) * | 2008-10-21 | 2018-05-05 | ||
| US8981027B2 (en) * | 2013-03-15 | 2015-03-17 | Henkel IP & Holding GmbH | Two-part, cyanoacrylate/cationically curable adhesive systems |
| CN104927680A (zh) * | 2014-03-17 | 2015-09-23 | 宁波百仕高联合工业有限公司 | 一种快固瞬间胶及其制备方法 |
| US9757898B2 (en) | 2014-08-18 | 2017-09-12 | Lord Corporation | Method for low temperature bonding of elastomers |
| ES2759052T3 (es) | 2014-09-12 | 2020-05-07 | Afinitica Tech S L | Adhesivo rápido y universal |
| EP2995663A1 (en) | 2014-09-12 | 2016-03-16 | Afinitica Technologies, S. L. | Fast and elastic adhesive |
| EP3124509A1 (en) | 2015-07-31 | 2017-02-01 | Afinitica Technologies, S. L. | Fast light curing cyanoacrylate compositions |
| GB2550846B (en) * | 2016-05-23 | 2021-01-13 | Henkel IP & Holding GmbH | Two-part Cyanoacrylate curable adhesive system |
| TWI752043B (zh) * | 2016-06-28 | 2022-01-11 | 日商東亞合成股份有限公司 | 2-氰基丙烯酸酯系接著劑組成物 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5567266A (en) | 1994-10-13 | 1996-10-22 | Loctite Corporation | Non-environmentally hazardous, non-volatile adhesive promoter composition for curing adhesives |
| JP2002533554A (ja) * | 1998-12-23 | 2002-10-08 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | シアノアクリレート接着剤のための活性剤 |
| US20080020126A1 (en) * | 2006-05-18 | 2008-01-24 | Armor Holdings Forensics Llc | Compound for and method of developing latent fingerprints |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1455941A (en) | 1920-08-30 | 1923-05-22 | Louis C Vanderlip | Vehicle steering mechanism |
| US3625930A (en) * | 1967-12-28 | 1971-12-07 | Loctite Corp | Anaerobic composition and process for bonding nonporous surfaces, said composition comprising an acrylic monomer a peroxy initiator and a bonding accelerator |
| IE36799B1 (en) * | 1971-12-14 | 1977-03-02 | Loctite Ltd | Cyanoacrylate adhesive composition |
| US3883592A (en) | 1972-04-20 | 1975-05-13 | Universal Oil Prod Co | Thiocarbamyl sulfenamides |
| CA1035342A (en) | 1974-01-04 | 1978-07-25 | American Cyanamid Company | Stabilized blends of accelerators (contain derivatives of acrylic acid and acrylamide) |
| JPS6055796B2 (ja) | 1978-02-08 | 1985-12-06 | 株式会社日立製作所 | 圧力管型原子炉 |
| GB8315977D0 (en) | 1983-06-10 | 1983-07-13 | Monsanto Europe Sa | Sulphur-containing polymers |
| JPS6222877A (ja) | 1985-07-23 | 1987-01-31 | Janome Sewing Mach Co Ltd | 部品の精密位置決め固着方法 |
| US5342645A (en) * | 1993-09-15 | 1994-08-30 | Minnesota Mining And Manufacturing Company | Metal complex/cyanoacrylate compositions useful in latent fingerprint development |
| US6001213A (en) * | 1994-10-13 | 1999-12-14 | Loctite Corporation | Methods for forming non-environmentally hazardous, non-volatile adhesive promoter compositions for curing adhesives |
| EP1009317A4 (en) * | 1997-08-28 | 2001-01-24 | Boston Scient Corp | SYSTEM FOR IMPLANTING CROSSLINKED POLYSACCHARIDE FIBER AND METHODS OF FORMING AND INSERTING THE SAME |
| US6512023B1 (en) * | 1998-06-18 | 2003-01-28 | Closure Medical Corporation | Stabilized monomer adhesive compositions |
| JP2001088815A (ja) * | 1999-09-17 | 2001-04-03 | Alpha Techno Co Ltd | ２−シアノアクリレート系組成物用ポリエチレン製容器 |
| DE60114605T2 (de) * | 2000-05-12 | 2006-07-27 | Loctite (R & D) Ltd., Tallaght | Aktivatorzusammensetzungen für cyanacrylatklebstoffe |
| DE60129603T2 (de) | 2001-01-08 | 2008-05-21 | Loctite (R & D) Ltd., Tallaght | Zu flexiblen polymermaterialien aushärtbare cyanoacrylatmassen |
| CN100352809C (zh) * | 2002-04-17 | 2007-12-05 | 西巴特殊化学品控股有限公司 | 氨基苯基苯并噻唑化合物 |
| JP2007125488A (ja) * | 2005-11-02 | 2007-05-24 | Omron Corp | 液状材料の吐出装置および液状材料の塗布装置ならびに液状材料の塗布方法 |
| JP2010516820A (ja) | 2006-07-13 | 2010-05-20 | エラストマー テクノロジーズ リミテッド | 天然および合成ゴムの再利用における改良および関連した改良 |
| CN101528835A (zh) | 2006-08-21 | 2009-09-09 | 国家有机化学工业有限公司 | 用于提高橡胶硫化胶网络稳定性的新型亚磺酰胺促进剂 |
| NO2346956T3 (enExample) * | 2008-10-21 | 2018-05-05 |
-
2009
- 2009-10-21 NO NO09740317A patent/NO2346956T3/no unknown
- 2009-10-21 WO PCT/EP2009/063833 patent/WO2010046412A1/en not_active Ceased
- 2009-10-21 ES ES09740317.4T patent/ES2656763T3/es active Active
- 2009-10-21 KR KR1020117011491A patent/KR101687424B1/ko active Active
- 2009-10-21 MX MX2011004279A patent/MX336405B/es unknown
- 2009-10-21 EP EP09740317.4A patent/EP2346956B1/en active Active
- 2009-10-21 HU HUE09740317A patent/HUE038460T2/hu unknown
- 2009-10-21 BR BRPI0919894A patent/BRPI0919894B1/pt active IP Right Grant
- 2009-10-21 CN CN200980146584.0A patent/CN102245725B/zh active Active
- 2009-10-21 PL PL09740317T patent/PL2346956T3/pl unknown
- 2009-10-21 JP JP2011532625A patent/JP5785083B2/ja active Active
- 2009-10-21 CA CA2741329A patent/CA2741329C/en active Active
-
2011
- 2011-04-20 US US13/090,589 patent/US8933168B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5567266A (en) | 1994-10-13 | 1996-10-22 | Loctite Corporation | Non-environmentally hazardous, non-volatile adhesive promoter composition for curing adhesives |
| JP2002533554A (ja) * | 1998-12-23 | 2002-10-08 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | シアノアクリレート接着剤のための活性剤 |
| US20080020126A1 (en) * | 2006-05-18 | 2008-01-24 | Armor Holdings Forensics Llc | Compound for and method of developing latent fingerprints |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102245725A (zh) | 2011-11-16 |
| ES2656763T3 (es) | 2018-02-28 |
| MX2011004279A (es) | 2011-06-01 |
| KR20110079731A (ko) | 2011-07-07 |
| BRPI0919894B1 (pt) | 2019-01-02 |
| EP2346956A1 (en) | 2011-07-27 |
| MX336405B (es) | 2016-01-18 |
| JP5785083B2 (ja) | 2015-09-24 |
| US20110196092A1 (en) | 2011-08-11 |
| HUE038460T2 (hu) | 2018-10-29 |
| PL2346956T3 (pl) | 2018-07-31 |
| CN102245725B (zh) | 2014-12-03 |
| NO2346956T3 (enExample) | 2018-05-05 |
| CA2741329C (en) | 2015-12-15 |
| US8933168B2 (en) | 2015-01-13 |
| EP2346956B1 (en) | 2017-12-06 |
| WO2010046412A1 (en) | 2010-04-29 |
| CA2741329A1 (en) | 2010-04-29 |
| JP2012506470A (ja) | 2012-03-15 |
| BRPI0919894A2 (pt) | 2016-02-16 |
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