JPH0447708B2 - - Google Patents
Info
- Publication number
- JPH0447708B2 JPH0447708B2 JP881585A JP881585A JPH0447708B2 JP H0447708 B2 JPH0447708 B2 JP H0447708B2 JP 881585 A JP881585 A JP 881585A JP 881585 A JP881585 A JP 881585A JP H0447708 B2 JPH0447708 B2 JP H0447708B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- reaction
- polymer
- added
- carbon atoms
- 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.)
- Expired
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 229920000642 polymer Polymers 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229920001651 Cyanoacrylate Polymers 0.000 description 11
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- -1 allyl ester Chemical class 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 239000002075 main ingredient Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- AKSXIZBBELQPSO-UHFFFAOYSA-N methyl-bis(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[SiH](C)OC(C)=C AKSXIZBBELQPSO-UHFFFAOYSA-N 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004830 Super Glue Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical class CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- WXKCRCGKCOKJEF-UHFFFAOYSA-N prop-2-enyl 2-cyanoacetate Chemical compound C=CCOC(=O)CC#N WXKCRCGKCOKJEF-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- BAACRKZNNZZIFO-UHFFFAOYSA-N 1-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CCC(S)[Si](C)(OC)OC BAACRKZNNZZIFO-UHFFFAOYSA-N 0.000 description 1
- OWOCLFMXKYUTDH-UHFFFAOYSA-N 1-trimethoxysilylpropane-1-thiol Chemical compound CCC(S)[Si](OC)(OC)OC OWOCLFMXKYUTDH-UHFFFAOYSA-N 0.000 description 1
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KWADETUNAHTOCO-UHFFFAOYSA-N C(C=C/C(=O)OCC1=CC=CC=C1)(=O)OCC1=CC=CC=C1.C(CCC)[Sn]CCCC Chemical compound C(C=C/C(=O)OCC1=CC=CC=C1)(=O)OCC1=CC=CC=C1.C(CCC)[Sn]CCCC KWADETUNAHTOCO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- AONDIGWFVXEZGD-UHFFFAOYSA-N diacetyloxy(methyl)silicon Chemical compound CC(=O)O[Si](C)OC(C)=O AONDIGWFVXEZGD-UHFFFAOYSA-N 0.000 description 1
- RWMHFANJOASIHT-UHFFFAOYSA-N dibenzyl 2-hydroxybutanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(O)CC(=O)OCC1=CC=CC=C1 RWMHFANJOASIHT-UHFFFAOYSA-N 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000004590 silicone sealant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- CWHJLNJICCBAOK-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-6-yl)ethyl]silane Chemical compound C1CCCC2OC21CC[Si](OC)(OC)OC CWHJLNJICCBAOK-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
（産業上の利用分野）
本発明は一成分型室温硬化性組成物、特には大
気中に曝露することによつて硬化し、耐熱性、耐
水性にすぐれた硬化物となる、接着剤、コーテイ
ング材、プライマーなどとして有用とされる一成
分型の室温硬化性組成物に関するものである。
（従来の技術）
室温硬化性組成物についてはオルガノシロキサ
ン系、ウレタン系、シアノアクリル酸系など各種
のものが公知とされているが、シアノアクリレー
ト単量体を主成分とするものは被着体表面に接す
ると瞬間的に重合して式
(Industrial Application Field) The present invention relates to a one-component room-temperature curable composition, particularly for use in adhesives and coatings, which cures when exposed to the atmosphere and becomes a cured product with excellent heat resistance and water resistance. The present invention relates to a one-component room-temperature curable composition useful as materials, primers, etc. (Prior art) Various types of room-temperature curable compositions are known, such as organosiloxane-based, urethane-based, and cyanoacrylic acid-based compositions, but those containing cyanoacrylate monomer as a main component are When it comes into contact with the surface, it instantly polymerizes and forms a formula.
【式】で
示される重合体となつて接着剤としての機能を発
揮することから瞬間接着剤と呼ばれている。
しかし、このシアノアクリレート系接着剤は瞬
間的に接触するという特徴をもつているものの、
硬化物としてのシアノアクリレートポリマーが熱
可塑性で耐熱性、耐水性に劣るというものである
ことからプライマー、コーテイング材として使用
したときに問題点があるという欠点をもつてい
る。
（発明の構成）
本発明は上記したような不利を解決したシアノ
アクリレート系の室温硬化性組成物に関するもの
であり、、これは一般式
（こゝにR1は炭素数１〜６の２価炭化水素基
または炭素数２〜８のチオエーテル結合を有する
２価炭化水素基、R2は炭素数１〜６の１価炭化
水素基、R3は炭素数１〜10の１価炭化水素基、
R4は水酸基または水素原子、Ｘは加水分解性基、
ａは１または２、ｍは１〜100、ｎは０〜100の整
数）で示される、分子量が1000〜30000である重
合体を主剤としてなることを特徴とするものであ
る。
これを説明すると本発明者は特に耐熱性、耐水
性のすぐれたシアノアクリレート系の室温硬化性
組成物について種々検討した結果、シアノアクリ
レートポリマー中にオルガノシリル基を導入すれ
ばこのような性質を有する組成物が得られるとい
うことに注目してこの合成を試み、上記した一般
式で示される重合体を試作し、この物性をしらべ
たところ、このものは式中に架橋可能な加水分解
性シリコーン官能基を含んでいるため空気中に曝
露されると室温で容易に硬化し、この硬化物は従
来公知のシアノアクリレートポリマーに比較して
すぐれた耐熱性、耐水性を示すので、接着剤、コ
テイング材、プライマーとして有用とされること
を確認して本発明を完成させた。
本発明の一成分型室温硬化性組成物は上記した
一般式(1)で示される、分子量が1000〜30000であ
る重合体を主剤としてなるものであるが、この重
合体におけるR1としては
−CH2−、−C2H4、−C3H6−、−C3H6SCH2−、
−C3H6SC2H4−などの基が、R2としては−CH3、
−C2H5、−C6H5などの基が、R3としては、CH3
−、C2H5−、C3H7−、C6H5−、CH3C6H4−な
どの基が例示され、またこのR4は水素原子、水
酸基とされ、Ｘはアルコキシ基、アシルオキシ
基、アミノ基、酸アミド基、オキシメート基、ケ
トキシメート基、アミノキシ基などのような加水
分解性基、ａ、ｍ、ｎは前記したような数値とさ
れるものであり、この重合体としては具体的に下
記のものが例示される。
本発明の組成物の主剤とされる前記した一般式
(1)で示される重合体はシアノアクリレートを製造
する公知の方法、例えばシアノ酢酸アリルエステ
ルとシアノ酢酸アルキルエステルとをホルムアル
デヒドと共に次式
（こゝにｂは０、１、２を示す）のように反応
させて下記
に示されている分子中に不飽和結合基を含むシア
ノアクリルポリマーを作つたのち、この不飽和結
合基に加水分解性シリコーン官能基を有するシリ
コーン化合物を付加反応させることによつて得る
ことができる。
上記した反応式(2)で示されるシアノアクリレー
トポリマーの合成反応におけるホルムアルデヒド
はパラホルムアルデヒドを使用してもよく、これ
にはピペラジン、ピロリジン、ピペリジン、トリ
エタノールアミンなどの塩基性化合物を触媒とし
て使用することがよいが、これはベンゼン、トル
エン、キシレン、ｎ−ヘキサン、シクロヘキサン
などのようにこの反応で生成する水と分離性のよ
い溶媒中で行なうことが好ましい。
つぎにこの反応で得られた式(3)で示されるシア
ノアクリレートポリマーと反応させる加水分解性
シリコーン官能基を有するシリコーン化合物は一
般式
（こゝにR2、Ｘ、ａは上記のとおり）で示さ
れるものとすればよく、このＸ基としてはアルコ
キシ基、アシルオキシ基、アミノ基、酸アミド
基、オキシメート基、ケトキシメート基、アミノ
キシ基などが例示され、これには具体的にトリメ
トキシシラン、トリエトキシシラン、メチルジメ
トキシシラン、メチルジエトキシシランなどのア
ルコキシシラン類、トリアセトキシシラン、メチ
ルジアセトキシシランなどのアシロキシシラン
類、トリ（メチルエチルケトオキシメート）シラ
ン、メチルジ（メチルエチルケトオキシメート）
シランなどのケトオキシメートシラン類、トリイ
ソプロペノキシシラン、メチルジイソプロペノキ
シシランなどのアルケノキシシラン類などが例示
される。
シアノアクリレートポリマーと上記した式(4)で
示されるオルガノシランとの反応は有機けい素化
学における付加反応用触媒として公知とされる塩
化白金酸、塩化白金酸とオレフインとの錯体、白
金黒、白金付き活性炭などの白金系触媒またはロ
ジウム、コバルト、パラジウム、ニツケルなどの
周規律表族の遷移金属錯体化合物触媒の存在下
に行なわせればよいが、この反応温度は30〜150
℃、好ましくは60〜120℃の範囲とすればよく、
この場合における溶剤の使用は任意とされるが好
ましくは脂肪族炭化水素、芳香族炭化水素、ハロ
ゲン化炭化水素、アルコール類などの溶剤中で行
なわせることがよい。
しかし、一般式(1)で示される重合体がそのR2
がチオエーテル結合を含む２価炭化水素基とされ
るものを得るためには、シアノアクリレートポリ
マーと反応させるオルガノシランを一般式
（式中のR2、Ｘ、ａは前記のとおり、R5は炭
素数１〜６の２価炭化水素基）で示されるメルカ
プトアルキル基を有するシランとする必要があ
り、この式(5)で示されるシランとしてはγ−メル
カプトプロピルトリメトキシシラン、γ−メルカ
プトプロピルメチルジメトキシシラン、α−メル
カプトプロピルトリメトキシシラン、α−メルカ
プトプロピルメチルジメトキシシランなどが例示
されるが、この反応はラジカル反応であることか
らこれにはベンゾイルパーオキサイド、アシルパ
ーオキサイドなどのパーオキサイド類、アゾビス
イソブチロニトリルなどのようなラジカル発生剤
を触媒として30〜150℃の温度で行なわせればよ
く、この際好ましくは脂肪族炭化水素、芳香族炭
化水素、ハロゲン化炭化水素などの溶剤を使用す
ればよい。
上記したような方法で得られた一般式(1)で示さ
れる重合体を主剤とする本発明の一成分型室温硬
化性組成物はこの重合体が加水分解性シリコーン
官能基を含むものであるため、の保存に当つては
水と接触しないように無水の状態に保つ必要があ
るが、保存中の安定性を維持するためには式
It is called an instant adhesive because it forms a polymer represented by the formula and functions as an adhesive. However, although this cyanoacrylate adhesive has the characteristic of instantaneous contact,
Since the cyanoacrylate polymer as a cured product is thermoplastic and has poor heat resistance and water resistance, it has the disadvantage of causing problems when used as a primer or coating material. (Structure of the Invention) The present invention relates to a cyanoacrylate-based room-temperature curable composition that solves the above-mentioned disadvantages. (R 1 is a divalent hydrocarbon group having 1 to 6 carbon atoms or a divalent hydrocarbon group having a thioether bond having 2 to 8 carbon atoms, R 2 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, R 3 is a monovalent hydrocarbon group having 1 to 10 carbon atoms,
R 4 is a hydroxyl group or a hydrogen atom, X is a hydrolyzable group,
A is 1 or 2, m is an integer of 1 to 100, and n is an integer of 0 to 100), and the polymer has a molecular weight of 1,000 to 30,000 as a main ingredient. To explain this, the present inventor conducted various studies on room-temperature curable cyanoacrylate compositions that have particularly excellent heat resistance and water resistance, and found that if an organosilyl group is introduced into a cyanoacrylate polymer, these properties can be obtained. Attempting this synthesis, we focused on the fact that a composition could be obtained, produced a prototype polymer represented by the above general formula, and examined its physical properties. Because it contains groups, it easily cures at room temperature when exposed to air, and this cured product exhibits superior heat resistance and water resistance compared to conventionally known cyanoacrylate polymers, making it suitable for adhesives and coating materials. The present invention was completed after confirming that the compound is useful as a primer. The one-component room temperature curable composition of the present invention is mainly composed of a polymer represented by the above general formula (1) and having a molecular weight of 1,000 to 30,000, and R 1 in this polymer is - CH 2 −, −C 2 H 4 , −C 3 H 6 −, −C 3 H 6 SCH 2 −,
Groups such as -C 3 H 6 SC 2 H 4 -, R 2 are -CH 3 ,
Groups such as -C 2 H 5 and -C 6 H 5 are CH 3 as R 3
Examples include groups such as -, C 2 H 5 -, C 3 H 7 -, C 6 H 5 -, CH 3 C 6 H 4 -, and R 4 is a hydrogen atom or a hydroxyl group, and X is an alkoxy group. , an acyloxy group, an amino group, an acid amide group, an oximate group, a ketoximate group, a hydrolyzable group such as an aminoxy group, a, m, n are the numerical values as described above, and as this polymer, Specifically, the following are exemplified. The above general formula used as the main ingredient of the composition of the present invention
The polymer represented by (1) can be prepared using a known method for producing cyanoacrylate, for example, by combining cyanoacetic allyl ester and cyanoacetic alkyl ester together with formaldehyde using the following formula: (Here, b represents 0, 1, or 2) by reacting as shown below. It can be obtained by making a cyanoacrylic polymer containing an unsaturated bond group in the molecule shown in , and then subjecting this unsaturated bond group to an addition reaction with a silicone compound having a hydrolyzable silicone functional group. . Paraformaldehyde may be used as the formaldehyde in the synthesis reaction of the cyanoacrylate polymer shown in reaction formula (2) above, and a basic compound such as piperazine, pyrrolidine, piperidine, or triethanolamine is used as a catalyst. However, this is preferably carried out in a solvent that is easily separable from the water produced in this reaction, such as benzene, toluene, xylene, n-hexane, and cyclohexane. Next, a silicone compound having a hydrolyzable silicone functional group to be reacted with the cyanoacrylate polymer represented by formula (3) obtained by this reaction has the general formula (wherein R 2 , Examples include alkoxysilanes such as trimethoxysilane, triethoxysilane, methyldimethoxysilane, and methyldiethoxysilane, acyloxysilanes such as triacetoxysilane and methyldiacetoxysilane, and tri( Methyl ethyl ketoxymate) silane, methyl di(methyl ethyl ketoxymate)
Examples include ketooxymate silanes such as silane, and alkenoxysilanes such as triisopropenoxysilane and methyldiisopropenoxysilane. The reaction between the cyanoacrylate polymer and the organosilane represented by the above formula (4) uses chloroplatinic acid, a complex of chloroplatinic acid and olefin, platinum black, and platinum, which are known as addition reaction catalysts in organosilicon chemistry. The reaction may be carried out in the presence of a platinum-based catalyst such as activated carbon or a complex compound catalyst of a transition metal of the cyclic group such as rhodium, cobalt, palladium, or nickel.
℃, preferably in the range of 60 to 120℃,
Although the use of a solvent in this case is optional, it is preferable to use a solvent such as an aliphatic hydrocarbon, an aromatic hydrocarbon, a halogenated hydrocarbon, or an alcohol. However, the polymer represented by general formula (1) has R 2
In order to obtain what is said to be a divalent hydrocarbon group containing a thioether bond, the organosilane reacted with the cyanoacrylate polymer has the general formula (In the formula, R 2 , X, and a are as described above, and R 5 is a divalent hydrocarbon group having 1 to 6 carbon atoms). Examples of the silane represented by are γ-mercaptopropyltrimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, α-mercaptopropyltrimethoxysilane, α-mercaptopropylmethyldimethoxysilane, etc., but this reaction is a radical reaction. For this reason, this can be carried out at a temperature of 30 to 150°C using a peroxide such as benzoyl peroxide or acyl peroxide, or a radical generator such as azobisisobutyronitrile as a catalyst. For this purpose, solvents such as aliphatic hydrocarbons, aromatic hydrocarbons, and halogenated hydrocarbons may be used. The one-component room-temperature curable composition of the present invention containing the polymer represented by the general formula (1) obtained by the method described above as a main ingredient contains a hydrolyzable silicone functional group; When storing it, it is necessary to keep it in an anhydrous state to avoid contact with water, but in order to maintain stability during storage, the formula
【式】（R2、Ｘ、ａは前記のとおり、
R6は炭素数１〜６の１価炭化水素基）で示され
るオルガノシランを組成物中の上記重合体に対し
０〜20重量％で添加しておくことがよい。
この組成物は空気中に曝露すると空気中の水分
との反応で室温で硬化するが、これにはその硬化
を促進するためにアルキルチタン酸塩、有機けい
素チタン酸塩、チタンキレート化合物などのチタ
ン化合物、オクチル酸すず、ジブチルすずジラウ
レート、ジブチルすずジベンジルマレートなどの
有機すず化合物、ジブチルアミン−２−エチルヘ
キソエート、テトラメチルグアニジン、テトラメ
チルグアニジルアルキル基を有する有機けい素化
合物などのアミン類を硬化促進剤として組成物に
対し0.001〜10重量の範囲で添加することが好ま
しい。
また、本発明の組成物にはこの組成物から得ら
れる硬化物の物性を改良する目的で充填剤を添加
してもよく、これには溶融シリカ、沈降性シリ
カ、カーボンブラツク、炭酸カルシウム、炭酸マ
グネシウム、けいそう土、石英粉末、酸化チタ
ン、酸化第二鉄、酸化亜鉛、タルク、石綿、ガラ
ス繊維などが例示されるが、これにはまた顔料、
紫外線吸収剤、酸化防止剤、界面活性剤、難燃
剤、絶縁剤などを目的に応じ添加してもよい。な
お、この組成物には必要に応じ接着性付与剤を添
加してもよく、これにはγ−アミノプロピルトリ
エトキシシラン、Ｎ−β−アミノエチル−γ−ア
ミノプロピルトリメトキシシラン、γ−メルカプ
トプロピルトリメトキシシラン、γ−メタクリロ
キシプロピルトリメトキシシラン、γ−グリシド
キシプロピルトリメトキシシラン、β−エポキシ
シクロヘキシルエチルトリメトキシシランなどの
ようなシランカツプリング剤と呼ばれている有機
官能性シラン化合物を添加すればよい。
本発明の一成分型室温硬化性組成物はその硬化
物が特に耐熱性、耐水性にすぐれているので建造
物、航空機、自動車、エレクトロニツクス、家電
製品などのシーリング剤、コーテイング剤、接着
剤、塗料などとして有用とされるが、これはまた
シリコーンシーリング材の表面コーテイング材と
して使用すればシリコーンによる目地周辺の汚染
が防止されるという硬化を与える。また、このも
のはガラス、コンクリート、磁器、木材、金属、
各種重合体、プラスチツク、塗料などともよく密
着するので、種々のタンクの密封用として、また
接着用としても使用することができるし、シリコ
ーン系、ポリサルフアイド系、ウレタン系のシー
リング材のプライマーとしても使用することがで
きる。なお、この組成物は特に溶剤を添加する必
要はないが、作業性をよくするために溶剤を添加
することは任意であり、これにはトルエン、キシ
レンなどの芳香族炭化水素、ヘキサン、シクロヘ
キサンなどの脂肪族炭化水素、パークロロエチレ
ン、トリクロロエチレン、フロンソルブなどのハ
ロゲン化炭化水素、さらにはジオクチルフタレー
ト、ジブチルフタレートなどの可塑剤を用いれば
よい。
つぎに本発明の実施例をあげるが、例中の部は
重量部を、また粘度は25℃での測定値を示したも
のである。
実施例 １
コンデンサーを付けた１の反応フラスコにシ
アノ酢酸アリルエステル25ｇ（0.2モル）、シアノ
酢酸エチルエステル90.4ｇ（0.8モル）、パラホル
ムアルデヒド30ｇ（１モル）、トルエン250ｇおよ
び触媒としてのピペリジン0.3ｇを仕込み、トル
エン還流下で反応させて生成する水を系外に除去
しながら５時間反応させ、水が18ｇ生成したとこ
ろで反応を終了させ、冷却後に１％塩酸水100ｇ
を添加して触媒を中和し、塩酸水層を分離してか
ら水洗により中和し、シリカゲルで脱水した。
ついで、この脱水した反応液を活性炭で処理し
てから過し、この液にγ−メルカプトプロピ
ルトリメトキシシラン39.3ｇ（0.2モル）、アゾビ
スイソブチロニトリル0.5ｇおよびメトキシハイ
ドロキノン0.2ｇを加えて80℃に加熱して３時間
反応させたところ、ガスクロマトグラフでしらべ
ても未反応のγ−メルカプトプロピルトリメトキ
シシランが検出されなかつたので反応は終結した
ものと判断し、120℃／10mmHgの条件下でトルエ
ンを留去したところ、粘度が22000cSで屈折率が
1.4761（25℃）の液体生成物145ｇが得られた。
つぎにこの重合体100部にジブチルすずジベン
ジルマレート２部を加えて均一に混合したのち、
これを空気中に曝露したところ、このものは２時
間後に硬化して非粘着性となり、これを2.0mmの
厚さにシート化して空気中に曝露したものは７日
後に硬化して硬度（シヨアーＡ）25、引張り強さ
７Kg／cm2、破断時の伸び80％という物性を示し
た。
実施例 ２
実施例１で得られたシリカゲルで脱水した反応
液に、トリメトキシシラン24.4ｇ（0.2モル）と
触媒としての塩化白金酸の２％イソプロピルアル
コール溶液１ｇを加え、90℃で４時間反応させた
のち120℃／10mmHgの条件下でトルエンを留去し
たところ、粘度が121000cSで屈折率が1.4771（25
℃）の粘稠な液体110ｇが得られた。
つぎにこの重合体100部にジブチルすずジラウ
レート１部とテトラメチルグアニジルプロピルト
リメトキシシラン１部を加えて均一な溶液とした
のち、空気中に曝露したところ、これは20分で非
粘着性のものとなつた。また、このものを厚さ
2.0mmのシートとしたものは７日後に硬化し、こ
れは硬度（シヨアーＡ）30、引張り強さ６Kg／
cm2、破断時の伸び70％という物性を示した。
実施例 ３
実施例１で得られたシリカゲルで脱水した反応
液に、メチルジイソプロペノキシシラン31.6ｇ
（0.2モル）と塩化白金酸の２％イソプロピルアル
コール溶液１ｇを加え、90℃で５時間反応させた
のち120℃／10mmHgの条件下でトルエンを留去し
たところ、粘度が34500cSで屈折率が1.4752（25
℃）の粘稠な液体120ｇが得られた。
つぎにこの重合体100部にテトラメチルグアニ
ジルプロピルトリメトキシシラン２部を加えて均
一な溶液としたのち、これを空気中に曝露したと
ころ、これは30分後に非粘着性となり、このもの
から作られた厚さ２mmのシートは７日後に硬化し
た硬度（シヨアーＡ）20、引張り強さ８Kg／cm2、
破断時の伸び75％という物性を示した。
実施例 ４
コンデンサー付き１の反応フラスコに、シア
ノ酢酸アリルエステル125ｇ、パラホルムアルデ
ヒド30ｇ、トルエン125ｇおよびピペリジン0.3ｇ
を仕込み、トルエン還流下に反応させて生成する
水を系外に除去しながら３時間反応させ、水の生
成が18ｇとなつたときに反応を終了させて冷却
し、１％の塩酸水で触媒を中和してから塩酸水層
を分離して水洗により中和してからシリカゲルで
脱水した。
ついでこの脱水した反応液を活性炭で処理して
から過し、この液に塩化白金酸の２％イソプ
ロピルアルコール溶液１ｇを加え80℃に加熱した
のち、こゝにメチルジイソプロペノキシシラン
158ｇを徐々に滴下し、80〜90℃で付加反応させ、
80℃に５時間保持してから120℃／10mmHgの条件
下でトルエンを留去したところ、表面に粘着性の
ある融点45℃の固体288ｇが得られた。
つぎにこの重合体をトルエンで50％に希釈した
もの100部にテトラメチルグアニジルプロピルト
リメトキシシラン１部を加えて均一に混合し、こ
れをガラス板上にコーテイングして空気中に曝露
したところ、これは30分間で非粘着性となり、４
日後に得られた硬化皮膜は鉛筆硬度2Hの硬度を
示した。
実施例 ５
実施例１〜４で得た重合体に第１表に示したよ
うにトルエンと有機すず化合物、グアニジルシラ
ンを加えてプライマーNo.１〜No.４を作り、これら
のプライマーをモルタル上に均一に塗布して30分
間風乾後、この上に室温硬化性シリコーンゴム組
成物・RTVKE−45〔信越化学工業（株）製商品
名〕をビード状に押出して試験片を作ると共に、
比較のために市販のシアノアクリレート系接着剤
を用いて同様の試験片を作り、ついでこのRTV
KE−45を室温で４日間放置して硬化させてその
接着性をしらべたところ、第２表に示したとおり
の結果が得られた。[Formula] (R 2 , X, a are as described above, R 6 is a monovalent hydrocarbon group having 1 to 6 carbon atoms) 0 to 20% by weight of the above polymer in the composition It is best to add it in When exposed to air, this composition cures at room temperature by reaction with moisture in the air, and contains alkyl titanates, organosilicon titanates, titanium chelate compounds, etc. to accelerate its curing. Titanium compounds, organotin compounds such as tin octylate, dibutyltin dilaurate, dibutyltin dibenzyl maleate, dibutylamine-2-ethylhexoate, tetramethylguanidine, organosilicon compounds having a tetramethylguanidylalkyl group It is preferable to add amines such as 0.001 to 10% by weight to the composition as a curing accelerator. Further, fillers may be added to the composition of the present invention for the purpose of improving the physical properties of the cured product obtained from the composition, and fillers include fused silica, precipitated silica, carbon black, calcium carbonate, carbonate Examples include magnesium, diatomaceous earth, quartz powder, titanium oxide, ferric oxide, zinc oxide, talc, asbestos, and glass fiber, but they also include pigments,
Ultraviolet absorbers, antioxidants, surfactants, flame retardants, insulating agents, etc. may be added depending on the purpose. Note that an adhesion imparting agent may be added to this composition if necessary, and examples thereof include γ-aminopropyltriethoxysilane, N-β-aminoethyl-γ-aminopropyltrimethoxysilane, and γ-mercapto. Organofunctional silane compounds called silane coupling agents such as propyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-epoxycyclohexylethyltrimethoxysilane, etc. All you have to do is add. The cured product of the one-component room-temperature curable composition of the present invention has particularly excellent heat resistance and water resistance, so it can be used as a sealant, coating agent, or adhesive for buildings, aircraft, automobiles, electronics, home appliances, etc. It is said to be useful as a paint, etc., but it also provides a hardening effect that prevents silicone from contaminating the joint area when used as a surface coating for silicone sealants. Also, this item can be made of glass, concrete, porcelain, wood, metal,
It adheres well to various polymers, plastics, paints, etc., so it can be used for sealing various tanks and for adhesion, and it can also be used as a primer for silicone-based, polysulfide-based, and urethane-based sealants. can do. Although it is not necessary to add a solvent to this composition, it is optional to add a solvent to improve workability. aliphatic hydrocarbons, halogenated hydrocarbons such as perchlorethylene, trichlorethylene, and Freonsolve, and plasticizers such as dioctyl phthalate and dibutyl phthalate may be used. Next, examples of the present invention will be given, in which parts are parts by weight, and viscosity is a value measured at 25°C. Example 1 In a reaction flask with a condenser, 25 g (0.2 mol) of allyl cyanoacetate, 90.4 g (0.8 mol) of ethyl cyanoacetate, 30 g (1 mol) of paraformaldehyde, 250 g of toluene and 0.3 g of piperidine as a catalyst. The reaction was carried out under toluene reflux, and the water produced was removed from the system for 5 hours. The reaction was terminated when 18 g of water was produced, and after cooling, 100 g of 1% hydrochloric acid was added.
was added to neutralize the catalyst, and the aqueous hydrochloric acid layer was separated, neutralized by washing with water, and dehydrated with silica gel. Next, this dehydrated reaction solution was treated with activated carbon and filtered, and 39.3 g (0.2 mol) of γ-mercaptopropyltrimethoxysilane, 0.5 g of azobisisobutyronitrile and 0.2 g of methoxyhydroquinone were added to this solution. When heated to 80°C and reacted for 3 hours, no unreacted γ-mercaptopropyltrimethoxysilane was detected by gas chromatography, so the reaction was judged to have been completed and the conditions were changed to 120°C/10 mmHg. When toluene was distilled off, the viscosity was 22000cS and the refractive index was
145 g of liquid product of 1.4761 (25° C.) were obtained. Next, 2 parts of dibutyltin dibenzyl malate was added to 100 parts of this polymer and mixed uniformly.
When this was exposed to the air, it hardened and became non-adhesive after 2 hours, and when it was made into a sheet with a thickness of 2.0 mm and exposed to the air, it hardened after 7 days and had a hardness (shower). A) It exhibited physical properties of 25, tensile strength of 7 Kg/cm 2 and elongation at break of 80%. Example 2 24.4 g (0.2 mol) of trimethoxysilane and 1 g of a 2% isopropyl alcohol solution of chloroplatinic acid as a catalyst were added to the silica gel-dehydrated reaction solution obtained in Example 1, and the mixture was reacted at 90°C for 4 hours. When the toluene was distilled off under the conditions of 120℃/10mmHg, the viscosity was 121000cS and the refractive index was 1.4771 (25
110 g of a viscous liquid with a temperature of 110 °C was obtained. Next, 1 part of dibutyltin dilaurate and 1 part of tetramethylguanidylpropyltrimethoxysilane were added to 100 parts of this polymer to make a homogeneous solution. When exposed to air, it became non-tacky within 20 minutes. It became my property. You can also measure the thickness of this thing
The 2.0 mm sheet hardens after 7 days and has a hardness (Shore A) of 30 and a tensile strength of 6 kg/
cm 2 and elongation at break of 70%. Example 3 31.6 g of methyldiisopropenoxysilane was added to the silica gel-dehydrated reaction solution obtained in Example 1.
(0.2 mol) and 1 g of a 2% isopropyl alcohol solution of chloroplatinic acid were added and reacted at 90°C for 5 hours. When the toluene was distilled off under the conditions of 120°C/10 mmHg, the viscosity was 34500 cS and the refractive index was 1.4752. (twenty five
120 g of a viscous liquid with a temperature of 120 °C was obtained. Next, 2 parts of tetramethylguanidylpropyltrimethoxysilane were added to 100 parts of this polymer to make a homogeneous solution, and when this was exposed to air, it became non-tacky after 30 minutes. A sheet of 2 mm thick made from 2 mm hardened after 7 days has a hardness (Shor A) of 20, a tensile strength of 8 Kg/cm 2 ,
It exhibited physical properties of elongation at break of 75%. Example 4 In a reaction flask with a condenser, 125 g of allyl cyanoacetate, 30 g of paraformaldehyde, 125 g of toluene, and 0.3 g of piperidine.
The reaction was carried out under toluene reflux, and the water produced was removed from the system for 3 hours. When the amount of water produced reached 18 g, the reaction was terminated, cooled, and catalyzed with 1% hydrochloric acid. The hydrochloric acid aqueous layer was separated, neutralized by washing with water, and then dehydrated with silica gel. Next, this dehydrated reaction solution was treated with activated carbon and filtered, 1 g of a 2% isopropyl alcohol solution of chloroplatinic acid was added to this solution, heated to 80°C, and then methyldiisopropenoxysilane was added.
158g was gradually added dropwise and an addition reaction was carried out at 80-90℃.
After holding the mixture at 80°C for 5 hours, toluene was distilled off under conditions of 120°C/10 mmHg to obtain 288 g of a solid with a sticky surface and a melting point of 45°C. Next, 1 part of tetramethylguanidylpropyltrimethoxysilane was added to 100 parts of this polymer diluted to 50% with toluene, mixed uniformly, and this was coated on a glass plate and exposed to air. However, it became non-adhesive in 30 minutes and
The cured film obtained after several days had a pencil hardness of 2H. Example 5 Primers No. 1 to No. 4 were prepared by adding toluene, an organic tin compound, and guanidylsilane to the polymers obtained in Examples 1 to 4 as shown in Table 1, and these primers were placed on mortar. After applying it evenly and air drying for 30 minutes, a room temperature curable silicone rubber composition, RTVKE-45 (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.) was extruded on top of it in the form of a bead to make a test piece.
For comparison, a similar test piece was made using a commercially available cyanoacrylate adhesive, and then this RTV
When KE-45 was left to cure at room temperature for 4 days and its adhesive properties were examined, the results shown in Table 2 were obtained.
【表】【table】
【表】
接着性…○良好、△一部界面剥離、×界面剥
離。
[Table] Adhesion: ○ Good, △ Partial interfacial peeling, × Interfacial peeling.
Claims (1)
または炭素数２〜８のチオエーテル結合を有する
２価炭化水素基、R2は炭素数１〜６の１価炭化
水素基、R3は炭素数１〜10の１価炭化水素基、
R4は水酸基または水素原子、Ｘは加水分解性基、
ａは１または２、ｍは１〜100、ｎは０〜100の整
数）で示される、分子量が1000〜30000である重
合体を主剤としてなることを特徴とする一成分型
室温硬化性組成物。[Claims] 1. General formula (Here, R 1 is a divalent hydrocarbon group having 1 to 6 carbon atoms or a divalent hydrocarbon group having a thioether bond having 2 to 8 carbon atoms, R 2 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, R 3 is a monovalent hydrocarbon group having 1 to 10 carbon atoms,
R 4 is a hydroxyl group or a hydrogen atom, X is a hydrolyzable group,
a is 1 or 2, m is an integer of 1 to 100, and n is an integer of 0 to 100), and the molecular weight is 1,000 to 30,000. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP881585A JPS61168607A (en) | 1985-01-21 | 1985-01-21 | One-component room temperature-curable composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP881585A JPS61168607A (en) | 1985-01-21 | 1985-01-21 | One-component room temperature-curable composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61168607A JPS61168607A (en) | 1986-07-30 |
| JPH0447708B2 true JPH0447708B2 (en) | 1992-08-04 |
Family
ID=11703311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP881585A Granted JPS61168607A (en) | 1985-01-21 | 1985-01-21 | One-component room temperature-curable composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61168607A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2019669A1 (en) * | 1989-11-21 | 1991-05-21 | John Woods | Anionically polymerizable monomers, polymers thereof, and use of such polymers in photoresists |
| EP0459617A1 (en) * | 1990-04-27 | 1991-12-04 | Three Bond Co., Ltd. | Novel silicon containing alpha-cyanoacrylates |
| US5386047A (en) * | 1994-03-11 | 1995-01-31 | Loctite Corporation | Di-α-cyanopentadienoate disiloxane compounds for use in adhesives |
-
1985
- 1985-01-21 JP JP881585A patent/JPS61168607A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61168607A (en) | 1986-07-30 |
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