JP6365445B2 - Aminoalkylalkoxydisiloxane compound and method for producing the same - Google Patents
Aminoalkylalkoxydisiloxane compound and method for producing the same Download PDFInfo
- Publication number
- JP6365445B2 JP6365445B2 JP2015131630A JP2015131630A JP6365445B2 JP 6365445 B2 JP6365445 B2 JP 6365445B2 JP 2015131630 A JP2015131630 A JP 2015131630A JP 2015131630 A JP2015131630 A JP 2015131630A JP 6365445 B2 JP6365445 B2 JP 6365445B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- bis
- general formula
- formula
- compound represented
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims description 43
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 aminoalkyl alkoxy disiloxane compound Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 229910052740 iodine Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000011630 iodine Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VKWZFQHSIVFRCP-UHFFFAOYSA-N [diethoxy(3-piperazin-1-ylbutyl)silyl]oxy-diethoxy-(3-piperazin-1-ylbutyl)silane Chemical compound CC(CC[Si](O[Si](OCC)(OCC)CCC(N1CCNCC1)C)(OCC)OCC)N1CCNCC1 VKWZFQHSIVFRCP-UHFFFAOYSA-N 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- QMZIYOVXNRSBPI-UHFFFAOYSA-N 3-[[3-(diethylamino)propyl-dimethoxysilyl]oxy-dimethoxysilyl]-N,N-diethylpropan-1-amine Chemical compound C(C)N(CC)CCC[Si](O[Si](OC)(OC)CCCN(CC)CC)(OC)OC QMZIYOVXNRSBPI-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000012855 volatile organic compound Substances 0.000 description 4
- IWPMIEAUTKYPQW-UHFFFAOYSA-N 3-chloropropyl-[3-chloropropyl(diethoxy)silyl]oxy-diethoxysilane Chemical compound ClCCC[Si](O[Si](OCC)(OCC)CCCCl)(OCC)OCC IWPMIEAUTKYPQW-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005370 alkoxysilyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000012756 surface treatment agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 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
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000002704 decyl 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])* 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000000524 functional group Chemical group 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
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 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 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GKXDJYKZFZVASJ-UHFFFAOYSA-M tetrapropylazanium;iodide Chemical compound [I-].CCC[N+](CCC)(CCC)CCC GKXDJYKZFZVASJ-UHFFFAOYSA-M 0.000 description 2
- SMGSPBKMKYMJPQ-UHFFFAOYSA-M tetrapropylphosphanium;bromide Chemical compound [Br-].CCC[P+](CCC)(CCC)CCC SMGSPBKMKYMJPQ-UHFFFAOYSA-M 0.000 description 2
- CISYLVSCEPBMLO-UHFFFAOYSA-M tetrapropylphosphanium;iodide Chemical compound [I-].CCC[P+](CCC)(CCC)CCC CISYLVSCEPBMLO-UHFFFAOYSA-M 0.000 description 2
- 125000000101 thioether group Chemical group 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RTEYLFYPIYWRMR-UHFFFAOYSA-N 3-[[3-(diethylamino)propyl-ethoxy-methylsilyl]oxy-ethoxy-methylsilyl]-N,N-diethylpropan-1-amine Chemical compound C(C)N(CC)CCC[Si](O[Si](C)(OCC)CCCN(CC)CC)(C)OCC RTEYLFYPIYWRMR-UHFFFAOYSA-N 0.000 description 1
- XMIJAJIYNVCELZ-UHFFFAOYSA-N 3-[[3-(diethylamino)propyl-methoxy-methylsilyl]oxy-methoxy-methylsilyl]-N,N-diethylpropan-1-amine Chemical compound C(C)N(CC)CCC[Si](O[Si](C)(OC)CCCN(CC)CC)(C)OC XMIJAJIYNVCELZ-UHFFFAOYSA-N 0.000 description 1
- JLXXLZXMQYJAPW-UHFFFAOYSA-N 3-[[3-(dimethylamino)propyl-diethoxysilyl]oxy-diethoxysilyl]-N,N-dimethylpropan-1-amine Chemical compound CN(C)CCC[Si](O[Si](OCC)(OCC)CCCN(C)C)(OCC)OCC JLXXLZXMQYJAPW-UHFFFAOYSA-N 0.000 description 1
- VDHJVNAPIIJAPD-UHFFFAOYSA-N 3-[[3-(dimethylamino)propyl-dimethoxysilyl]oxy-dimethoxysilyl]-N,N-dimethylpropan-1-amine Chemical compound CN(C)CCC[Si](O[Si](OC)(OC)CCCN(C)C)(OC)OC VDHJVNAPIIJAPD-UHFFFAOYSA-N 0.000 description 1
- PSPSEEQYOQMXLO-UHFFFAOYSA-N 3-[[3-[bis(trimethylsilyl)amino]propyl-dimethoxysilyl]oxy-dimethoxysilyl]-N,N-bis(trimethylsilyl)propan-1-amine Chemical compound C[Si](C)(C)N([Si](C)(C)C)CCC[Si](O[Si](OC)(OC)CCCN([Si](C)(C)C)[Si](C)(C)C)(OC)OC PSPSEEQYOQMXLO-UHFFFAOYSA-N 0.000 description 1
- QSOQTAWJFXVJQY-UHFFFAOYSA-N 3-[[3-[bis(trimethylsilyl)amino]propyl-methoxy-methylsilyl]oxy-methoxy-methylsilyl]-N,N-bis(trimethylsilyl)propan-1-amine Chemical compound C[Si](C)(C)N([Si](C)(C)C)CCC[Si](O[Si](C)(OC)CCCN([Si](C)(C)C)[Si](C)(C)C)(C)OC QSOQTAWJFXVJQY-UHFFFAOYSA-N 0.000 description 1
- KUYUGFSVVRMHSM-UHFFFAOYSA-N 3-[bis(trimethylsilyl)methoxy-dimethoxysilyl]propan-1-amine Chemical compound C[Si](C)(C)C(O[Si](OC)(OC)CCCN)[Si](C)(C)C KUYUGFSVVRMHSM-UHFFFAOYSA-N 0.000 description 1
- WHIUXPZYOZFVNT-UHFFFAOYSA-N 3-[bis(trimethylsilyl)methoxy-methoxy-methylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(OC)OC([Si](C)(C)C)[Si](C)(C)C WHIUXPZYOZFVNT-UHFFFAOYSA-N 0.000 description 1
- HCBHAYZGECJCGL-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]-n,n-diethylpropan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN(CC)CC HCBHAYZGECJCGL-UHFFFAOYSA-N 0.000 description 1
- ZZNRMMYTKJBVPD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]-n,n-dimethylpropan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN(C)C ZZNRMMYTKJBVPD-UHFFFAOYSA-N 0.000 description 1
- FHLZUEPKLGQEQP-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCC[Si](C)(OC)OC FHLZUEPKLGQEQP-UHFFFAOYSA-N 0.000 description 1
- JXNGSNLOFNAVJI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n,n-dimethylpropan-1-amine Chemical compound CO[Si](C)(OC)CCCN(C)C JXNGSNLOFNAVJI-UHFFFAOYSA-N 0.000 description 1
- UNVFWCQQWZUPLB-UHFFFAOYSA-N 3-[dimethoxy(pentan-3-yloxy)silyl]propan-1-amine Chemical compound CCC(CC)O[Si](OC)(OC)CCCN UNVFWCQQWZUPLB-UHFFFAOYSA-N 0.000 description 1
- RFWJSTVYJNEJAU-UHFFFAOYSA-N 3-bromopropyl-(3-bromopropyl-ethoxy-methylsilyl)oxy-ethoxy-methylsilane Chemical compound BrCCC[Si](O[Si](C)(OCC)CCCBr)(C)OCC RFWJSTVYJNEJAU-UHFFFAOYSA-N 0.000 description 1
- NNOMXRJBQRTHRE-UHFFFAOYSA-N 3-bromopropyl-(3-bromopropyl-methoxy-methylsilyl)oxy-methoxy-methylsilane Chemical compound CO[Si](C)(CCCBr)O[Si](C)(CCCBr)OC NNOMXRJBQRTHRE-UHFFFAOYSA-N 0.000 description 1
- MYOFCBOKPFKXLS-UHFFFAOYSA-N 3-bromopropyl-[3-bromopropyl(diethoxy)silyl]oxy-diethoxysilane Chemical compound BrCCC[Si](O[Si](OCC)(OCC)CCCBr)(OCC)OCC MYOFCBOKPFKXLS-UHFFFAOYSA-N 0.000 description 1
- VFDXAXFHZFLANI-UHFFFAOYSA-N 3-bromopropyl-[3-bromopropyl(dimethoxy)silyl]oxy-dimethoxysilane Chemical compound BrCCC[Si](O[Si](OC)(OC)CCCBr)(OC)OC VFDXAXFHZFLANI-UHFFFAOYSA-N 0.000 description 1
- SCMLMWUCIPYYEG-UHFFFAOYSA-N 3-chloropropyl-(3-chloropropyl-ethoxy-methylsilyl)oxy-ethoxy-methylsilane Chemical compound CCO[Si](C)(CCCCl)O[Si](C)(CCCCl)OCC SCMLMWUCIPYYEG-UHFFFAOYSA-N 0.000 description 1
- JLXDVUVAEOBVQS-UHFFFAOYSA-N 3-chloropropyl-(3-chloropropyl-methoxy-methylsilyl)oxy-methoxy-methylsilane Chemical compound ClCCC[Si](C)(OC)O[Si](C)(CCCCl)OC JLXDVUVAEOBVQS-UHFFFAOYSA-N 0.000 description 1
- NBYBEFXVAARUMZ-UHFFFAOYSA-N 3-chloropropyl-[3-chloropropyl(dimethoxy)silyl]oxy-dimethoxysilane Chemical compound ClCCC[Si](OC)(OC)O[Si](CCCCl)(OC)OC NBYBEFXVAARUMZ-UHFFFAOYSA-N 0.000 description 1
- YDKDHVSSNQIMJR-UHFFFAOYSA-N 3-iodopropyl-(3-iodopropyl-methoxy-methylsilyl)oxy-methoxy-methylsilane Chemical compound CO[Si](C)(CCCI)O[Si](C)(CCCI)OC YDKDHVSSNQIMJR-UHFFFAOYSA-N 0.000 description 1
- XIEGNAOGFBSWQC-UHFFFAOYSA-N 3-iodopropyl-[3-iodopropyl(dimethoxy)silyl]oxy-dimethoxysilane Chemical compound ICCC[Si](O[Si](OC)(OC)CCCI)(OC)OC XIEGNAOGFBSWQC-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- AZUHFEJVUXVADQ-UHFFFAOYSA-N 4-bromobutyl-(4-bromobutyl-methoxy-methylsilyl)oxy-methoxy-methylsilane Chemical compound CO[Si](C)(CCCCBr)O[Si](C)(CCCCBr)OC AZUHFEJVUXVADQ-UHFFFAOYSA-N 0.000 description 1
- PWOFHTFREMZXRV-UHFFFAOYSA-N 4-bromobutyl-[4-bromobutyl(diethoxy)silyl]oxy-diethoxysilane Chemical compound BrCCCC[Si](O[Si](OCC)(OCC)CCCCBr)(OCC)OCC PWOFHTFREMZXRV-UHFFFAOYSA-N 0.000 description 1
- ZOPGFUNYGWLMCO-UHFFFAOYSA-N 4-bromobutyl-[4-bromobutyl(dimethoxy)silyl]oxy-dimethoxysilane Chemical compound BrCCCC[Si](O[Si](OC)(OC)CCCCBr)(OC)OC ZOPGFUNYGWLMCO-UHFFFAOYSA-N 0.000 description 1
- JFFKJENXQGXHEL-UHFFFAOYSA-N 4-chlorobutyl-(4-chlorobutyl-methoxy-methylsilyl)oxy-methoxy-methylsilane Chemical compound CO[Si](C)(CCCCCl)O[Si](C)(CCCCCl)OC JFFKJENXQGXHEL-UHFFFAOYSA-N 0.000 description 1
- SVYCBWOFFUPGMS-UHFFFAOYSA-N 4-chlorobutyl-[4-chlorobutyl(diethoxy)silyl]oxy-diethoxysilane Chemical compound ClCCCC[Si](O[Si](OCC)(OCC)CCCCCl)(OCC)OCC SVYCBWOFFUPGMS-UHFFFAOYSA-N 0.000 description 1
- GNEAZOUCWUJWID-UHFFFAOYSA-N 4-chlorobutyl-[4-chlorobutyl(dimethoxy)silyl]oxy-dimethoxysilane Chemical compound ClCCCC[Si](O[Si](OC)(OC)CCCCCl)(OC)OC GNEAZOUCWUJWID-UHFFFAOYSA-N 0.000 description 1
- XHCYZSAUQNGMNG-UHFFFAOYSA-N 4-iodobutyl-(4-iodobutyl-methoxy-methylsilyl)oxy-methoxy-methylsilane Chemical compound CO[Si](C)(CCCCI)O[Si](C)(CCCCI)OC XHCYZSAUQNGMNG-UHFFFAOYSA-N 0.000 description 1
- HQIJUHIXIWPNCW-UHFFFAOYSA-N 4-iodobutyl-[4-iodobutyl(dimethoxy)silyl]oxy-dimethoxysilane Chemical compound CO[Si](CCCCI)(OC)O[Si](CCCCI)(OC)OC HQIJUHIXIWPNCW-UHFFFAOYSA-N 0.000 description 1
- WDUAYVHCYGZARQ-UHFFFAOYSA-N 4-prop-1-enylmorpholine Chemical group CC=CN1CCOCC1 WDUAYVHCYGZARQ-UHFFFAOYSA-N 0.000 description 1
- HACWLUQYAGTGKY-UHFFFAOYSA-N C[Si](C)(C)C(C)(O[Si](OCC)(OCC)CCCN)[Si](C)(C)C Chemical compound C[Si](C)(C)C(C)(O[Si](OCC)(OCC)CCCN)[Si](C)(C)C HACWLUQYAGTGKY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- SGJKEULVMWOEPM-UHFFFAOYSA-N N-butyl-N-[3-[[3-(dibutylamino)propyl-diethoxysilyl]oxy-diethoxysilyl]propyl]butan-1-amine Chemical compound CCCCN(CCCC)CCC[Si](OCC)(OCC)O[Si](CCCN(CCCC)CCCC)(OCC)OCC SGJKEULVMWOEPM-UHFFFAOYSA-N 0.000 description 1
- CBMKQUSWWXRTJQ-UHFFFAOYSA-N N-butyl-N-[3-[[3-(dibutylamino)propyl-dimethoxysilyl]oxy-dimethoxysilyl]propyl]butan-1-amine Chemical compound C(CCC)N(CCCC)CCC[Si](O[Si](OC)(OC)CCCN(CCCC)CCCC)(OC)OC CBMKQUSWWXRTJQ-UHFFFAOYSA-N 0.000 description 1
- SXEZXELGUYJQRH-UHFFFAOYSA-N N-butyl-N-[3-[[3-(dibutylamino)propyl-ethoxy-methylsilyl]oxy-ethoxy-methylsilyl]propyl]butan-1-amine Chemical compound CCCCN(CCCC)CCC[Si](C)(OCC)O[Si](C)(CCCN(CCCC)CCCC)OCC SXEZXELGUYJQRH-UHFFFAOYSA-N 0.000 description 1
- YEQHMRSFXZTEQY-UHFFFAOYSA-N N-butyl-N-[3-[[3-(dibutylamino)propyl-methoxy-methylsilyl]oxy-methoxy-methylsilyl]propyl]butan-1-amine Chemical compound C(CCC)N(CCCC)CCC[Si](O[Si](C)(OC)CCCN(CCCC)CCCC)(C)OC YEQHMRSFXZTEQY-UHFFFAOYSA-N 0.000 description 1
- HKSHDAROCUPLGS-UHFFFAOYSA-N O1CCN(CC1)CCC[Si](O[Si](C)(OC)CCCN1CCOCC1)(C)OC Chemical compound O1CCN(CC1)CCC[Si](O[Si](C)(OC)CCCN1CCOCC1)(C)OC HKSHDAROCUPLGS-UHFFFAOYSA-N 0.000 description 1
- AJLBFPFJALBUTR-UHFFFAOYSA-N O1CCN(CC1)CCC[Si](O[Si](C)(OCC)CCCN1CCOCC1)(C)OCC Chemical compound O1CCN(CC1)CCC[Si](O[Si](C)(OCC)CCCN1CCOCC1)(C)OCC AJLBFPFJALBUTR-UHFFFAOYSA-N 0.000 description 1
- FTYGICHWKHPKAJ-UHFFFAOYSA-N [diethoxy(3-iodopropyl)silyl]oxy-diethoxy-(3-iodopropyl)silane Chemical compound ICCC[Si](O[Si](OCC)(OCC)CCCI)(OCC)OCC FTYGICHWKHPKAJ-UHFFFAOYSA-N 0.000 description 1
- DRAASPBJJUEPOC-UHFFFAOYSA-N [dimethoxy(3-piperazin-1-ylbutyl)silyl]oxy-dimethoxy-(3-piperazin-1-ylbutyl)silane Chemical compound CC(CC[Si](OC)(OC)O[Si](CCC(C)N1CCNCC1)(OC)OC)N2CCNCC2 DRAASPBJJUEPOC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- XSLNSDFYDNBEHP-UHFFFAOYSA-N diethoxy-(3-piperazin-1-ylpropyl)-propan-2-yloxysilane Chemical compound CC(C)O[Si](OCC)(OCC)CCCN1CCNCC1 XSLNSDFYDNBEHP-UHFFFAOYSA-N 0.000 description 1
- UPQSLTRGZOJYDB-UHFFFAOYSA-N diethoxy-methyl-(3-morpholin-4-ylpropyl)silane Chemical compound CCO[Si](C)(OCC)CCCN1CCOCC1 UPQSLTRGZOJYDB-UHFFFAOYSA-N 0.000 description 1
- LPJGNMYFZQJTPW-UHFFFAOYSA-N diethoxy-methyl-(3-piperazin-1-ylpropyl)silane Chemical compound CCO[Si](C)(OCC)CCCN1CCNCC1 LPJGNMYFZQJTPW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- DUVRRNWJXAYEHK-UHFFFAOYSA-N dimethoxy-methyl-(3-morpholin-4-ylpropyl)silane Chemical compound CO[Si](C)(OC)CCCN1CCOCC1 DUVRRNWJXAYEHK-UHFFFAOYSA-N 0.000 description 1
- CTLDFURRFMJGON-UHFFFAOYSA-N dimethoxy-methyl-(3-piperazin-1-ylpropyl)silane Chemical compound CO[Si](C)(OC)CCCN1CCNCC1 CTLDFURRFMJGON-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- HCFPRFJJTHMING-UHFFFAOYSA-N ethane-1,2-diamine;hydron;chloride Chemical compound [Cl-].NCC[NH3+] HCFPRFJJTHMING-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ZPCMTZSWEMKEGU-UHFFFAOYSA-N ethoxy(silyloxy)silane Chemical compound CCO[SiH2]O[SiH3] ZPCMTZSWEMKEGU-UHFFFAOYSA-N 0.000 description 1
- QOGPCRXMWSITFT-UHFFFAOYSA-N ethoxy-[ethoxy-(3-iodopropyl)-methylsilyl]oxy-(3-iodopropyl)-methylsilane Chemical compound CCO[Si](C)(CCCI)O[Si](C)(CCCI)OCC QOGPCRXMWSITFT-UHFFFAOYSA-N 0.000 description 1
- FBLXOROHJQCQHJ-UHFFFAOYSA-N ethoxy-[ethoxy-(4-iodobutyl)-methylsilyl]oxy-(4-iodobutyl)-methylsilane Chemical compound CCO[Si](C)(CCCCI)O[Si](C)(CCCCI)OCC FBLXOROHJQCQHJ-UHFFFAOYSA-N 0.000 description 1
- YQCLTDJCGVMZDS-UHFFFAOYSA-N ethoxy-[ethoxy-methyl-(3-piperazin-1-ylbutyl)silyl]oxy-methyl-(3-piperazin-1-ylbutyl)silane Chemical compound CCO[Si](C)(CCC(C)N1CCNCC1)O[Si](C)(CCC(C)N2CCNCC2)OCC YQCLTDJCGVMZDS-UHFFFAOYSA-N 0.000 description 1
- GNJLPZUKOSKZPQ-UHFFFAOYSA-N ethoxy-[ethoxy-methyl-(3-piperazin-1-ylpropyl)silyl]oxy-methyl-(3-piperazin-1-ylpropyl)silane Chemical compound N1(CCNCC1)CCC[Si](O[Si](C)(OCC)CCCN1CCNCC1)(C)OCC GNJLPZUKOSKZPQ-UHFFFAOYSA-N 0.000 description 1
- IHPBUAOREMMYAY-UHFFFAOYSA-N ethoxy-methoxy-methyl-(3-piperazin-1-ylpropyl)silane Chemical compound CCO[Si](OC)(C)CCCN1CCNCC1 IHPBUAOREMMYAY-UHFFFAOYSA-N 0.000 description 1
- DCMOZUVYKDQMEE-UHFFFAOYSA-N ethoxy-methyl-(3-piperazin-1-ylpropyl)-propan-2-yloxysilane Chemical compound CCO[Si](C)(CCCN1CCNCC1)OC(C)C DCMOZUVYKDQMEE-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- CVLRIKZNIQKIRN-UHFFFAOYSA-N methoxy-[methoxy-methyl-(3-piperazin-1-ylbutyl)silyl]oxy-methyl-(3-piperazin-1-ylbutyl)silane Chemical compound CC(CC[Si](C)(OC)O[Si](C)(CCC(C)N1CCNCC1)OC)N2CCNCC2 CVLRIKZNIQKIRN-UHFFFAOYSA-N 0.000 description 1
- IMSCDVPUZJHYQZ-UHFFFAOYSA-N methoxy-[methoxy-methyl-(3-piperazin-1-ylpropyl)silyl]oxy-methyl-(3-piperazin-1-ylpropyl)silane Chemical compound N1(CCNCC1)CCC[Si](O[Si](C)(OC)CCCN1CCNCC1)(C)OC IMSCDVPUZJHYQZ-UHFFFAOYSA-N 0.000 description 1
- OFLMWACNYIOTNX-UHFFFAOYSA-N methyl(methylsilyloxy)silane Chemical compound C[SiH2]O[SiH2]C OFLMWACNYIOTNX-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BVBBZEKOMUDXMZ-UHFFFAOYSA-N n,n-diethyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCN(CC)CC BVBBZEKOMUDXMZ-UHFFFAOYSA-N 0.000 description 1
- AQIQPUUNTCVHBS-UHFFFAOYSA-N n,n-dimethyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCN(C)C AQIQPUUNTCVHBS-UHFFFAOYSA-N 0.000 description 1
- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 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
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 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
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- XHSMJSNXQUKFBB-UHFFFAOYSA-N triethoxy(3-morpholin-4-ylpropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCOCC1 XHSMJSNXQUKFBB-UHFFFAOYSA-N 0.000 description 1
- CQERQNNEKFKVFU-UHFFFAOYSA-N triethoxy(3-piperazin-1-ylpropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCNCC1 CQERQNNEKFKVFU-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-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
- YJDOIAGBSYPPCK-UHFFFAOYSA-N trimethoxy(3-morpholin-4-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1CCOCC1 YJDOIAGBSYPPCK-UHFFFAOYSA-N 0.000 description 1
- HXYMWKLNCJPAKW-UHFFFAOYSA-N trimethoxy(3-piperazin-1-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1CCNCC1 HXYMWKLNCJPAKW-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Silicon Polymers (AREA)
Description
本発明は、新規な２つのアミノ基を有するアルコキシジシロキサン化合物及びその製造方法に関する。この新規化合物は、シランカップリング剤、樹脂添加剤、塗料添加剤、接着剤、繊維処理剤、表面処理剤として有用である。 The present invention relates to a novel alkoxydisiloxane compound having two amino groups and a method for producing the same. This novel compound is useful as a silane coupling agent, a resin additive, a paint additive, an adhesive, a fiber treatment agent, and a surface treatment agent.
アミノ基を有するシラン化合物は、シランカップリング剤、樹脂添加剤、塗料添加剤、接着剤、繊維処理剤、表面処理剤として有用である。アミノ基を有するシラン化合物としては、３−アミノプロピルトリメトキシシラン等が知られているが、分子内に加水分解性の官能基を多数含むことから、使用時に発生する揮発性有機化合物（ＶＯＣ）の量が多く、環境への負荷が懸念されている。 Silane compounds having an amino group are useful as silane coupling agents, resin additives, paint additives, adhesives, fiber treatment agents, and surface treatment agents. As the silane compound having an amino group, 3-aminopropyltrimethoxysilane and the like are known, but volatile organic compounds (VOC) generated at the time of use since they contain many hydrolyzable functional groups in the molecule. There are many concerns about the environmental impact.
この問題を解決するため、二分子の３−アミノプロピルトリアルコキシシランを縮合させた１，３−ビス（３−アミノプロピル）−１，１，３，３−テトラアルコキシジシロキサンが開発されている（非特許文献１）。このようなアルコキシジシロキサン化合物は、対応するモノマーと比較して分子量が大きいため、揮発性が低下し、取り扱いが容易である。また、一分子当たりのアルコキシ基が増加していることから、これに由来する効果の増強が期待される（特許文献１）。更に、単位重量当たりのＶＯＣがモノマーよりも少なくなることから、環境への負荷も小さい。 In order to solve this problem, 1,3-bis (3-aminopropyl) -1,1,3,3-tetraalkoxydisiloxane obtained by condensing bimolecular 3-aminopropyltrialkoxysilane has been developed. (Non-Patent Document 1). Such an alkoxydisiloxane compound has a large molecular weight as compared with the corresponding monomer, and therefore has low volatility and is easy to handle. Moreover, since the alkoxy group per molecule is increasing, the effect derived from this is anticipated (patent document 1). Furthermore, since the VOC per unit weight is less than that of the monomer, the burden on the environment is small.
しかしながら、これまでに開発されたアルコキシジシロキサン化合物は、いずれも一級又は二級アミノ基を持つ化合物であり、窒素上に反応性に富む活性水素を有している。このため、エポキシ樹脂前駆体、ポリウレタン前駆体、カーボネート樹脂等に添加した場合、副反応を起こす等して、しばしば問題になることがある。例えば、エポキシ樹脂前駆体に上記化合物を添加した場合、上記化合物自体がエポキシ基を開環してしまうため、樹脂の硬化が進行してしまう。また、ポリウレタン前駆体、すなわち、イソシアネート基を含む化合物に上記化合物を添加した場合、ウレタン樹脂の骨格そのものにアルコキシジシロキサン化合物が組み込まれてしまう。更に、カーボネート樹脂に上記化合物を添加した場合、炭酸エステル骨格がアミド骨格へと変換されてしまい、樹脂が分解されてしまうことが考えられる。このため、アルコキシジシロキサン化合物の特性を持ちながら、多様な用途に使用できる化合物が求められていた。 However, all the alkoxydisiloxane compounds developed so far are compounds having a primary or secondary amino group and have active hydrogen rich in reactivity on nitrogen. For this reason, when it adds to an epoxy resin precursor, a polyurethane precursor, carbonate resin, etc., it may cause a side reaction etc., and may become a problem often. For example, when the above compound is added to the epoxy resin precursor, the compound itself opens the epoxy group, and the curing of the resin proceeds. Moreover, when the said compound is added to a polyurethane precursor, ie, the compound containing an isocyanate group, an alkoxy disiloxane compound will be incorporated in the skeleton of the urethane resin itself. Further, when the above compound is added to the carbonate resin, it is considered that the carbonate skeleton is converted to the amide skeleton and the resin is decomposed. For this reason, the compound which has the characteristic of an alkoxy disiloxane compound and can be used for various uses was calculated | required.
本発明は、上記事情に鑑みなされたもので、アルコキシジシロキサン化合物の特性を持ちながら、多様な用途に使用できるアミノアルキルアルコキシジシロキサン化合物及びその製造方法を提供することを目的とする。 This invention is made | formed in view of the said situation, and it aims at providing the aminoalkyl alkoxy disiloxane compound which can be used for various uses, and its manufacturing method, while having the characteristic of an alkoxy disiloxane compound.
本発明者らは、上記課題を解決するため鋭意検討を重ねた結果、活性水素を持たないアミノアルキルアルコキシジシロキサン化合物が多様な用途で使用できることを見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above problems, the present inventors have found that aminoalkylalkoxydisiloxane compounds having no active hydrogen can be used in various applications, and have completed the present invention.
従って、本発明は、下記に示すアミノアルキルアルコキシジシロキサン化合物及びその製造方法を提供する。
〔１〕
下記一般式（１）
〔２〕
下記一般式（２）
で示されるアミノアルキルアルコキシシラン化合物を加水分解縮合させることを特徴とする〔１〕記載の一般式（１）で示されるアミノアルキルアルコキシジシロキサン化合物の製造方法。
〔３〕
下記一般式（３）
で示されるハロアルキルアルコキシジシロキサン化合物と、下記一般式（４）
で示されるアミン化合物を反応させることを特徴とする〔１〕記載の一般式（１）で示されるアミノアルキルアルコキシジシロキサン化合物の製造方法。
Accordingly, the present invention provides the following aminoalkylalkoxydisiloxane compounds and methods for producing the same.
[1]
The following general formula (1)
[2]
The following general formula (2)
The method for producing an aminoalkylalkoxydisiloxane compound represented by the general formula (1) according to [1], wherein the aminoalkylalkoxysilane compound represented by the formula (1) is hydrolyzed and condensed.
[3]
The following general formula (3)
A haloalkylalkoxydisiloxane compound represented by the following general formula (4):
A process for producing an aminoalkylalkoxydisiloxane compound represented by the general formula (1) according to [1], wherein the amine compound represented by formula (1) is reacted.
本発明により提供されるアミノアルキルアルコキシジシロキサン化合物は、使用時にアミノ基とアルコキシシリル基の効果を十分に発揮でき、且つ使用時に発生する揮発性有機化合物が少ないため、シランカップリング剤、樹脂添加剤、表面処理剤、塗料添加剤、接着剤等として有用である。 The aminoalkylalkoxydisiloxane compound provided by the present invention can fully exhibit the effects of amino groups and alkoxysilyl groups during use, and since there are few volatile organic compounds generated during use, a silane coupling agent, resin addition It is useful as an agent, a surface treatment agent, a paint additive, an adhesive and the like.
本発明のアミノアルキルアルコキシジシロキサン化合物は、下記一般式（１）で示される化合物である。
ここで、Ｒ1、Ｒ2の炭素数１〜２０の１価炭化水素基として、具体的には、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、デシル基等の直鎖状アルキル基、イソプロピル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、テキシル基、２−エチルヘキシル基等の分岐状アルキル基、シクロペンチル基、シクロヘキシル基等の環状アルキル基、ビニル基、プロペニル基等のアルケニル基等が例示され、特に原料の調達容易性から、エチル基が好ましい。また、Ｒ1、Ｒ2の炭素数１〜２０の１価炭化水素基は、エステル基（−ＣＯＯ−）、エーテル基（−Ｏ−）、スルフィド基（−Ｓ−）等のヘテロ原子が介在していてもよく、これらを組み合わせて用いることもできる。更に、これらの炭化水素基の水素原子の一部又は全部が置換されていてもよく、該置換基としては、具体的には、例えば、メトキシ基、エトキシ基、（イソ）プロポキシ基等のアルコキシ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子；シアノ基；アミノ基；フェニル基、トリル基等の炭素数６〜１０のアリール基、ベンジル基、フェネチル基等の炭素数７〜１０のアラルキル基、炭素数２〜１０のアシル基；それぞれ各アルキル基、各アルコキシ基が炭素数１〜５であるトリアルキルシリル基、トリアルコキシシリル基、ジアルキルモノアルコキシシリル基、モノアルキルジアルコキシシリル基等が挙げられる。 Here, as the monovalent hydrocarbon group R 1, the number of carbon atoms in R 2 1 to 20, specifically, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group A linear alkyl group such as decyl group, a branched alkyl group such as isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, texyl group and 2-ethylhexyl group, and cyclic alkyl group such as cyclopentyl group and cyclohexyl group Group, vinyl group, alkenyl group such as propenyl group and the like are exemplified, and ethyl group is particularly preferable from the viewpoint of easy procurement of raw materials. In addition, the monovalent hydrocarbon group having 1 to 20 carbon atoms of R 1 and R 2 includes a hetero atom such as an ester group (—COO—), an ether group (—O—), or a sulfide group (—S—). These may be used, and these may be used in combination. Furthermore, some or all of the hydrogen atoms of these hydrocarbon groups may be substituted. Specific examples of the substituent include alkoxy groups such as a methoxy group, an ethoxy group, and an (iso) propoxy group. Group: halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; cyano group; amino group; carbon number 7 such as aryl group having 6 to 10 carbon atoms such as phenyl group and tolyl group, benzyl group and phenethyl group -10 aralkyl groups, C2-C10 acyl groups; each alkyl group, each alkoxy group having 1 to 5 carbon atoms, a trialkylsilyl group, a trialkoxysilyl group, a dialkylmonoalkoxysilyl group, a monoalkyldi An alkoxysilyl group etc. are mentioned.
また、Ｒ1、Ｒ2が互いに結合してこれらが結合する窒素原子と共に環構造を形成して下記式（５）で示される基となる場合には、ピロリジン基、ピペリジン基、ピペラジン基、メチルピペラジン基、モルホリン基等が例示される。
また、Ｒ3のヘテロ原子を含んでもよい炭素数１〜２０の２価炭化水素基として、具体的には、メチレン基、エチレン基、プロピレン基、ブチレン基、ヘキサメチレン基、オクタメチレン基、デシレン基等の直鎖状のアルキレン基、メチルエチレン基、メチルプロピレン基等の分岐状アルキレン基、シクロヘキシレン基等の環状アルキレン基、プロペニレン基等のアルケニレン基、フェニレン基等のアリーレン基、メチレンフェニレン基、メチレンフェニレンメチレン基等のアラルキレン基等が例示され、特に原料の調達容易性からメチレン基が好ましい。また、Ｒ3の２価炭化水素基は、エステル基（−ＣＯＯ−）、エーテル基（−Ｏ−）、スルフィド基（−Ｓ−）等のヘテロ原子が介在していてもよく、これらを組み合わせて用いることもできる。更に、これらの炭化水素基の水素原子の一部又は全部が置換されていてもよく、該置換基としては、上記Ｒ1、Ｒ2の炭化水素基の水素原子の一部又は全部が置換されていてもよい置換基と同様の置換基が挙げられる。 Further, as the divalent hydrocarbon group of carbon atoms which may contain a hetero atom having 1 to 20 of R 3, specifically, methylene group, ethylene group, propylene group, butylene group, hexamethylene group, octamethylene group, decylene Linear alkylene group such as a group, branched alkylene group such as methylethylene group and methylpropylene group, cyclic alkylene group such as cyclohexylene group, alkenylene group such as propenylene group, arylene group such as phenylene group, methylenephenylene group And an aralkylene group such as a methylenephenylenemethylene group, etc., and a methylene group is particularly preferred from the viewpoint of easy procurement of raw materials. In addition, the divalent hydrocarbon group of R 3 may be intervened by heteroatoms such as an ester group (—COO—), an ether group (—O—), a sulfide group (—S—), etc. Can also be used. Furthermore, some or all of the hydrogen atoms of these hydrocarbon groups may be substituted, and as the substituent, some or all of the hydrogen atoms of the hydrocarbon groups of R 1 and R 2 are substituted. The same substituent as the substituent which you may have is mentioned.
Ｒ4及びＲ5の炭素数１〜１０の１価炭化水素基として、具体的には、メチル基、エチル基、ヘキシル基、オクチル基、デシル基等の直鎖状アルキル基、イソプロピル基、ｔｅｒｔ−ブチル基、ネオペンチル基、テキシル基等の分岐状アルキル基、シクロペンチル基、シクロヘキシル基等の環状アルキル基、ビニル基、アリル基、プロペニル基等のアルケニル基、フェニル基、トリル基等のアリール基、ベンジル基、フェネチル基等のアラルキル基等が例示され、特に原料の調達容易性からアルキル基が好ましく、生成物の有用性からメチル基、エチル基が好ましい。 Specific examples of the monovalent hydrocarbon group having 1 to 10 carbon atoms of R 4 and R 5 include a linear alkyl group such as a methyl group, an ethyl group, a hexyl group, an octyl group, and a decyl group, an isopropyl group, and a tert group. -Branched alkyl groups such as butyl group, neopentyl group and texyl group; cyclic alkyl groups such as cyclopentyl group and cyclohexyl group; alkenyl groups such as vinyl group, allyl group and propenyl group; aryl groups such as phenyl group and tolyl group; Examples thereof include aralkyl groups such as benzyl group and phenethyl group, and alkyl groups are particularly preferred from the viewpoint of easy procurement of raw materials, and methyl groups and ethyl groups are preferred from the usefulness of the product.
上記一般式（１）で示されるアミノアルキルアルコキシジシロキサン化合物としては、１，３−ビス（ジメチルアミノプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（ジメチルアミノプロピル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ジメチルアミノプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（ジメチルアミノプロピル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ジエチルアミノプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（ジエチルアミノプロピル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ジエチルアミノプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（ジエチルアミノプロピル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ジブチルアミノプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（ジブチルアミノプロピル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ジブチルアミノプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（ジブチルアミノプロピル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（モルホリノプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（モルホリノプロピル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（モルホリノプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（モルホリノプロピル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ピペラジノプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（ピペラジノプロピル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ピペラジノプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（ピペラジノプロピル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（メチルピペラジノプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（メチルピペラジノプロピル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（メチルピペラジノプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（メチルピペラジノプロピル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ビス（トリメチルシリル）アミノプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（ビス（トリメチルシリル）アミノプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（ビス（トリメチルシリル）アミノプロピル）−１，３−ジメトキシ−１，３−ジメチルジシロキサン、１，３−ビス（ビス（トリメチルシリル）アミノプロピル）−１，３−ジエトキシ−１，３−ジメチルジシロキサン等が例示される。 Examples of the aminoalkylalkoxydisiloxane compound represented by the general formula (1) include 1,3-bis (dimethylaminopropyl) -1,1,3,3-tetramethoxydisiloxane and 1,3-bis (dimethylamino). Propyl) -1,3-dimethoxy-1,3-dimethyl-disiloxane, 1,3-bis (dimethylaminopropyl) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (dimethylamino) Propyl) -1,3-diethoxy-1,3-dimethyl-disiloxane, 1,3-bis (diethylaminopropyl) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (diethylaminopropyl) -1,3-dimethoxy-1,3-dimethyl-disiloxane, 1,3-bis (diethylaminopropyl) -1,1,3,3-teto Ethoxydisiloxane, 1,3-bis (diethylaminopropyl) -1,3-diethoxy-1,3-dimethyl-disiloxane, 1,3-bis (dibutylaminopropyl) -1,1,3,3-tetramethoxy Disiloxane, 1,3-bis (dibutylaminopropyl) -1,3-dimethoxy-1,3-dimethyl-disiloxane, 1,3-bis (dibutylaminopropyl) -1,1,3,3-tetraethoxy Disiloxane, 1,3-bis (dibutylaminopropyl) -1,3-diethoxy-1,3-dimethyl-disiloxane, 1,3-bis (morpholinopropyl) -1,1,3,3-tetramethoxydi Siloxane, 1,3-bis (morpholinopropyl) -1,3-dimethoxy-1,3-dimethyl-disiloxane, 1,3-bis (morpholinopropylene ) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (morpholinopropyl) -1,3-diethoxy-1,3-dimethyl-disiloxane, 1,3-bis (piperazinopropyl) ) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (piperazinopropyl) -1,3-dimethoxy-1,3-dimethyl-disiloxane, 1,3-bis (piperazi) Nopropyl) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (piperazinopropyl) -1,3-diethoxy-1,3-dimethyl-disiloxane, 1,3-bis ( Methylpiperazinopropyl) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (methylpiperazinopropyl) -1,3-dimethoxy-1,3-dimethyl-disiloxane, 1, 3-bis ( Methylpiperazinopropyl) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (methylpiperazinopropyl) -1,3-diethoxy-1,3-dimethyl-disiloxane, 1, 3-bis (bis (trimethylsilyl) aminopropyl) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (bis (trimethylsilyl) aminopropyl) -1,1,3,3-tetraethoxydi Siloxane, 1,3-bis (bis (trimethylsilyl) aminopropyl) -1,3-dimethoxy-1,3-dimethyldisiloxane, 1,3-bis (bis (trimethylsilyl) aminopropyl) -1,3-diethoxy- Examples include 1,3-dimethyldisiloxane.
式（１）で示されるアミノアルキルアルコキシジシロキサン化合物は、窒素上に反応性に富む活性水素を持たないことから、エポキシ樹脂前駆体に添加しても、開環重合が引き起こされない。また、ポリウレタン前駆体、すなわち、イソシアネート基を含むものと混合してもイソシアネート基と反応しないため、樹脂の骨格自体に添加剤が組み込まれることは避けられる。カーボネート樹脂に添加しても、カーボネート骨格を分解しない。また、アミノ基部位とアルコキシシリル基部位が十分に離れていることから、それぞれの官能基が互いに効果を阻害することが少ない。 Since the aminoalkylalkoxydisiloxane compound represented by the formula (1) does not have reactive hydrogen on nitrogen, ring-opening polymerization is not caused even when it is added to the epoxy resin precursor. Moreover, since it does not react with an isocyanate group even when mixed with a polyurethane precursor, that is, one containing an isocyanate group, incorporation of an additive into the resin skeleton itself is avoided. Addition to carbonate resin does not decompose carbonate skeleton. In addition, since the amino group site and the alkoxysilyl group site are sufficiently separated from each other, the respective functional groups rarely interfere with each other.
本発明におけるアミノアルキルアルコキシジシロキサン化合物の製造方法としては、例えば、下記一般式（２）
で示されるアミノアルキルアルコキシシラン化合物を加水分解縮合して製造できる。
As a manufacturing method of the aminoalkyl alkoxy disiloxane compound in this invention, following General formula (2) is mentioned, for example.
It can manufacture by hydrolytic condensation of the aminoalkyl alkoxysilane compound shown by these.
上記一般式（２）で示されるアミノアルキルアルコキシシラン化合物としては、ジメチルアミノプロピルトリメトキシシラン、ジエチルアミノプロピルトリメトキシシラン、ジブチルアミノプロピルトリメトキシシラン、ピペラジノプロピルトリメトキシシラン、メチルピペラジノプロピルトリメトキシシラン、モルホリノプロピルトリメトキシシラン、ジメチルアミノプロピルトリエトキシシラン、ジエチルアミノプロピルトリエトキシシラン、ジブチルアミノプロピルトリエトキシシラン、ピペラジノプロピルトリエトキシシラン、メチルピペラジノプロピルトリエトキシシラン、モルホリノプロピルトリエトキシシラン、ジメチルアミノプロピルメチルジメトキシシラン、ジエチルアミノプロピルメチルジメトキシシラン、ジブチルアミノプロピルメチルジメトキシシラン、ピペラジノプロピルメチルジメトキシシラン、メチルピペラジノプロピルメチルジメトキシシラン、モルホリノプロピルメチルジメトキシシラン、ジメチルアミノプロピルメチルジエトキシシラン、ジエチルアミノプロピルメチルジエトキシシラン、ジブチルアミノプロピルメチルジエトキシシラン、ピペラジノプロピルメチルジエトキシシラン、メチルピペラジノプロピルメチルジエトキシシラン、モルホリノプロピルメチルジエトキシシラン、ビス（トリメチルシリル）アミノプロピルトリメトキシシラン、ビス（トリメチルシリル）アミノプロピルトリエトキシシラン、ビス（トリメチルシリル）アミノプロピルメチルジメトキシシラン、ビス（トリメチルシリル）アミノプロピルメチルジエトキシシラン等が例示される。 Examples of the aminoalkylalkoxysilane compound represented by the general formula (2) include dimethylaminopropyltrimethoxysilane, diethylaminopropyltrimethoxysilane, dibutylaminopropyltrimethoxysilane, piperazinopropyltrimethoxysilane, and methylpiperazinopropyl. Trimethoxysilane, morpholinopropyltrimethoxysilane, dimethylaminopropyltriethoxysilane, diethylaminopropyltriethoxysilane, dibutylaminopropyltriethoxysilane, piperazinopropyltriethoxysilane, methylpiperazinopropyltriethoxysilane, morpholinopropyltri Ethoxysilane, dimethylaminopropylmethyldimethoxysilane, diethylaminopropylmethyldimethoxysilane, dibutyla Nopropylmethyldimethoxysilane, piperazinopropylmethyldimethoxysilane, methylpiperazinopropylmethyldimethoxysilane, morpholinopropylmethyldimethoxysilane, dimethylaminopropylmethyldiethoxysilane, diethylaminopropylmethyldiethoxysilane, dibutylaminopropylmethyldiethoxy Silane, piperazinopropylmethyldiethoxysilane, methylpiperazinopropylmethyldiethoxysilane, morpholinopropylmethyldiethoxysilane, bis (trimethylsilyl) aminopropyltrimethoxysilane, bis (trimethylsilyl) aminopropyltriethoxysilane, bis ( Trimethylsilyl) aminopropylmethyldimethoxysilane, bis (trimethylsilyl) aminopropylmethyldiet Shishiran like.
上記一般式（２）で示されるアミノアルキルアルコキシシラン化合物と水の配合比は、特に限定されないが、反応性、生産性の点から、一般式（２）で示される化合物１モルに対し、水を０．１〜４モル、特に０．２〜１モルの範囲が好ましい。 The mixing ratio of the aminoalkylalkoxysilane compound represented by the general formula (2) and water is not particularly limited, but from the viewpoint of reactivity and productivity, water is added to 1 mol of the compound represented by the general formula (2). In the range of 0.1 to 4 mol, particularly 0.2 to 1 mol.
加水分解縮合反応は無触媒でも進行するが、触媒を添加することで反応速度を改善することもできる。用いられる触媒としては、ナトリウムメトキシド、ナトリウムエトキシド等及びそのアルコール溶液、カリウムメトキシド、カリウムエトキシド、水酸化ナトリウム、水酸化カリウム、水酸化セシウム、水酸化カルシウム、水酸化マグネシウム、トリエチルアミン、トリブチルアミン、トリオクチルアミン等の塩基性触媒、塩化水素、臭化水素、硫酸、メタンスルホン酸、ベンゼンスルホン酸、ドデシルベンゼンスルホン酸、トリフルオロメタンスルホン酸、酢酸、トリフルオロ酢酸等の酸性触媒、テトラプロピルアンモニウムブロミド、テトラブチルアンモニウムブロミド、テトラプロピルアンモニウムヨージド、テトラブチルアンモニウムヨージド等の４級アンモニウム塩、テトラプロピルホスホニウムブロミド、テトラブチルホスホニウムブロミド、テトラプロピルホスホニウムヨージド、テトラブチルホスホニウムヨージド等の４級ホスホニウム塩等が挙げられる。 The hydrolysis condensation reaction proceeds even without a catalyst, but the reaction rate can be improved by adding a catalyst. Examples of the catalyst used include sodium methoxide, sodium ethoxide and the like and alcohol solutions thereof, potassium methoxide, potassium ethoxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, calcium hydroxide, magnesium hydroxide, triethylamine, triethylamine, Basic catalysts such as butylamine and trioctylamine, acidic catalysts such as hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, benzenesulfonic acid, dodecylbenzenesulfonic acid, trifluoromethanesulfonic acid, acetic acid and trifluoroacetic acid, tetrapropyl Quaternary ammonium salts such as ammonium bromide, tetrabutylammonium bromide, tetrapropylammonium iodide, tetrabutylammonium iodide, tetrapropylphosphonium bromide, tetrabutylphosphonium Muburomido, tetrapropyl phosphonium iodide, quaternary phosphonium salts such as tetrabutylphosphonium iodide, and the like.
触媒の使用量は特に限定されないが、反応促進効果の観点から、一般式（２）で示される化合物１モルに対し、触媒を０．００１〜１．０モル、特に０．００１〜０．２モル、とりわけ０．００５〜０．１モル用いるのが好ましい。 Although the usage-amount of a catalyst is not specifically limited, From a viewpoint of reaction promotion effect, a catalyst is 0.001-1.0 mol with respect to 1 mol of compounds shown by General formula (2), Especially 0.001-0.2. It is preferable to use mol, especially 0.005 to 0.1 mol.
加水分解縮合反応は無溶媒でも進行するが、溶媒を用いることもできる。用いられる溶媒としては、ペンタン、ヘキサン、シクロヘキサン、ヘプタン、イソオクタン、ベンゼン、トルエン、キシレン等の炭化水素系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ジエチルエーテル、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、アセトニトリル、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド等の非プロトン性極性溶媒が例示される。これらの溶媒は、１種を単独で使用してもよく、あるいは２種以上を混合してもよい。特に、水の局所的な存在を防ぐため、非プロトン性極性溶媒やアルコール系溶媒を用いることが望ましい。 The hydrolysis condensation reaction proceeds even without solvent, but a solvent can also be used. Solvents used include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene and xylene, alcohol solvents such as methanol, ethanol and isopropanol, and ether solvents such as diethyl ether, tetrahydrofuran and dioxane. And aprotic polar solvents such as acetonitrile, N, N-dimethylformamide and N, N-dimethylacetamide. These solvent may be used individually by 1 type, or may mix 2 or more types. In particular, in order to prevent the local presence of water, it is desirable to use an aprotic polar solvent or an alcohol solvent.
加水分解縮合反応の反応温度は特に限定されないが、２０〜２００℃、特に３０〜１００℃が好ましく、反応時間も特に限定されないが、１〜３０時間、特に３〜１０時間が好ましい。 The reaction temperature of the hydrolysis-condensation reaction is not particularly limited, but 20 to 200 ° C., particularly 30 to 100 ° C. is preferable, and the reaction time is not particularly limited, but 1 to 30 hours, particularly 3 to 10 hours is preferable.
また、別の方法として、下記一般式（３）
で示されるハロアルキルアルコキシジシロキサン化合物と、下記一般式（４）
で示されるアミン化合物を反応させることで、上記一般式（１）で示されるアミノアルキルアルコキシジシロキサン化合物を製造できる。
As another method, the following general formula (3)
A haloalkylalkoxydisiloxane compound represented by the following general formula (4):
By reacting the amine compound represented by the formula (1), the aminoalkylalkoxydisiloxane compound represented by the general formula (1) can be produced.
上記一般式（３）で示されるハロアルキルアルコキシジシロキサン化合物としては、１，３−ビス（クロロプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（クロロプロピル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（クロロプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（クロロプロピル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（クロロブチル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（クロロブチル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（クロロブチル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（クロロブチル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ブロモプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（ブロモプロピル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ブロモプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（ブロモプロピル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ブロモブチル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（ブロモブチル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ブロモブチル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（ブロモブチル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ヨードプロピル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（ヨードプロピル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ヨードプロピル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（ヨードプロピル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ヨードブチル）−１，１，３，３−テトラメトキシジシロキサン、１，３−ビス（ヨードブチル）−１，３−ジメトキシ−１，３−ジメチル−ジシロキサン、１，３−ビス（ヨードブチル）−１，１，３，３−テトラエトキシジシロキサン、１，３−ビス（ヨードブチル）−１，３−ジエトキシ−１，３−ジメチル−ジシロキサン等が例示される。 Examples of the haloalkylalkoxydisiloxane compound represented by the general formula (3) include 1,3-bis (chloropropyl) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (chloropropyl)- 1,3-dimethoxy-1,3-dimethyl-disiloxane, 1,3-bis (chloropropyl) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (chloropropyl) -1, 3-diethoxy-1,3-dimethyl-disiloxane, 1,3-bis (chlorobutyl) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (chlorobutyl) -1,3-dimethoxy- 1,3-dimethyl-disiloxane, 1,3-bis (chlorobutyl) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (chlorobutyl) -1,3-di Toxi-1,3-dimethyl-disiloxane, 1,3-bis (bromopropyl) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (bromopropyl) -1,3-dimethoxy- 1,3-dimethyl-disiloxane, 1,3-bis (bromopropyl) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (bromopropyl) -1,3-diethoxy-1, 3-dimethyl-disiloxane, 1,3-bis (bromobutyl) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (bromobutyl) -1,3-dimethoxy-1,3-dimethyl- Disiloxane, 1,3-bis (bromobutyl) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (bromobutyl) -1,3-diethoxy-1,3-dimethyl-disilo Sun, 1,3-bis (iodopropyl) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (iodopropyl) -1,3-dimethoxy-1,3-dimethyl-disiloxane, 1,3-bis (iodopropyl) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (iodopropyl) -1,3-diethoxy-1,3-dimethyl-disiloxane, 1, 3-bis (iodobutyl) -1,1,3,3-tetramethoxydisiloxane, 1,3-bis (iodobutyl) -1,3-dimethoxy-1,3-dimethyl-disiloxane, 1,3-bis ( Examples include iodobutyl) -1,1,3,3-tetraethoxydisiloxane, 1,3-bis (iodobutyl) -1,3-diethoxy-1,3-dimethyl-disiloxane, and the like.
上記一般式（４）で示されるアミン化合物としては、ジメチルアミン、ジエチルアミン、ジブチルアミン、ピペラジン、メチルピペラジン、モルホリン、ピロリジン、ピペリジン等が例示される。 Examples of the amine compound represented by the general formula (4) include dimethylamine, diethylamine, dibutylamine, piperazine, methylpiperazine, morpholine, pyrrolidine, and piperidine.
一般式（３）で示されるハロアルキルアルコキシジシロキサン化合物と、一般式（４）で示されるアミン化合物の反応割合は、反応の迅速な進行、後処理の簡便さ、精製の容易さ等の観点から、一般式（３）で示される化合物１モルに対し、一般式（４）で示されるアミン化合物を４〜２０モル、特に４〜８モル用いるのが好ましい。 The reaction ratio between the haloalkylalkoxydisiloxane compound represented by the general formula (3) and the amine compound represented by the general formula (4) is from the viewpoint of rapid progress of the reaction, ease of post-treatment, ease of purification, etc. It is preferable to use 4 to 20 mol, particularly 4 to 8 mol, of the amine compound represented by the general formula (4) with respect to 1 mol of the compound represented by the general formula (3).
一般式（３）で示されるハロアルキルアルコキシジシロキサン化合物と、一般式（４）で示されるアミン化合物の反応は無触媒でも進行するが、触媒を加えることで、反応速度が向上することもある。用いられる触媒としては、テトラプロピルアンモニウムブロミド、テトラブチルアンモニウムブロミド、テトラプロピルアンモニウムヨージド、テトラブチルアンモニウムヨージド等の４級アンモニウム塩、テトラプロピルホスホニウムブロミド、テトラブチルホスホニウムブロミド、テトラプロピルホスホニウムヨージド、テトラブチルホスホニウムヨージド等の４級ホスホニウム塩が例示される。 The reaction of the haloalkylalkoxydisiloxane compound represented by the general formula (3) and the amine compound represented by the general formula (4) proceeds even without a catalyst, but the reaction rate may be improved by adding a catalyst. Examples of the catalyst used include quaternary ammonium salts such as tetrapropylammonium bromide, tetrabutylammonium bromide, tetrapropylammonium iodide, tetrabutylammonium iodide, tetrapropylphosphonium bromide, tetrabutylphosphonium bromide, tetrapropylphosphonium iodide, Quaternary phosphonium salts such as tetrabutylphosphonium iodide are exemplified.
触媒の使用量は特に限定されないが、反応促進効果の観点から、一般式（３）で示される化合物１モルに対し、触媒を０．００１〜１．０モル、特に０．００１〜０．２モル、とりわけ０．００５〜０．１モル用いるのが好ましい。 Although the usage-amount of a catalyst is not specifically limited, From a viewpoint of reaction promotion effect, a catalyst is 0.001-1.0 mol with respect to 1 mol of compounds shown by General formula (3), Especially 0.001-0.2. It is preferable to use mol, especially 0.005 to 0.1 mol.
一般式（３）で示されるハロアルキルアルコキシジシロキサン化合物と、一般式（４）で示されるアミン化合物の反応は無溶媒でも進行するが、溶媒を加えることもできる。用いられる溶媒としては、ペンタン、ヘキサン、シクロヘキサン、ヘプタン、イソオクタン、ベンゼン、トルエン、キシレン等の炭化水素系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ジエチルエーテル、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、アセトニトリル、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、Ｎ−メチルピロリドン等の非プロトン性極性溶媒が例示される。これらの溶媒は、１種を単独で使用してもよく、あるいは２種以上を混合してもよい。特に、反応速度向上が期待できるエーテル系溶媒、非プロトン性極性溶媒を用いることが望ましい。 The reaction of the haloalkylalkoxydisiloxane compound represented by the general formula (3) and the amine compound represented by the general formula (4) proceeds even without a solvent, but a solvent can be added. Solvents used include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene and xylene, alcohol solvents such as methanol, ethanol and isopropanol, and ether solvents such as diethyl ether, tetrahydrofuran and dioxane. And aprotic polar solvents such as acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, and N-methylpyrrolidone. These solvent may be used individually by 1 type, or may mix 2 or more types. In particular, it is desirable to use an ether solvent or an aprotic polar solvent that can be expected to improve the reaction rate.
反応温度も特に限定されないが、２０〜２００℃、特に５０〜１５０℃が好ましく、反応時間も特に限定されないが、１〜３０時間、特に３〜１０時間が好ましい。 The reaction temperature is not particularly limited, but is preferably 20 to 200 ° C, particularly 50 to 150 ° C, and the reaction time is not particularly limited, but is preferably 1 to 30 hours, particularly 3 to 10 hours.
以下、実施例及び比較例を示して、本発明を具体的に説明するが、本発明は下記の実施例に制限されるものではない。 EXAMPLES Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated concretely, this invention is not restrict | limited to the following Example.
［実施例１］１，３−ビス（ジエチルアミノプロピル）−１，１，３，３−テトラメトキシジシロキサンの合成
撹拌機、還流器、滴下ロート及び温度計を備えたフラスコに、ジエチルアミノプロピルトリメトキシシラン１，５００ｇ（６．３７２モル）と水３４．９ｇ（１．９４モル）を仕込み、７０℃で５時間撹拌した。反応液を蒸留し、１５８℃／０．２ｋＰａの留分（１，３−ビス（ジエチルアミノプロピル）−１，１，３，３−テトラメトキシジシロキサン）を２９６．３ｇ得た。
Example 1 Synthesis of 1,3-bis (diethylaminopropyl) -1,1,3,3-tetramethoxydisiloxane Into a flask equipped with a stirrer, reflux, dropping funnel and thermometer, was added diethylaminopropyltrimethoxy. 1,500 g (6.372 mol) of silane and 34.9 g (1.94 mol) of water were charged and stirred at 70 ° C. for 5 hours. The reaction solution was distilled to obtain 296.3 g of a fraction (1,3-bis (diethylaminopropyl) -1,1,3,3-tetramethoxydisiloxane) at 158 ° C./0.2 kPa.
得られた留分の質量スペクトル、1Ｈ−ＮＭＲスペクトル、ＩＲスペクトルを測定した。
質量スペクトル
ｍ／ｚ ４２４ ３６３ １６７ ８６
ＩＲスペクトル
図１にチャートで示す。
1Ｈ−ＮＭＲスペクトル（重クロロホルム溶媒）
図２にチャートで示す。
以上の結果より、得られた化合物は、１，３−ビス（ジエチルアミノプロピル）−１，１，３，３−テトラメトキシジシロキサンであることが確認された。
A mass spectrum, 1 H-NMR spectrum, and IR spectrum of the obtained fraction were measured.
Mass spectrum m / z 424 363 167 86
IR spectrum FIG. 1 is a chart.
1 H-NMR spectrum (deuterated chloroform solvent)
FIG. 2 is a chart.
From the above results, it was confirmed that the obtained compound was 1,3-bis (diethylaminopropyl) -1,1,3,3-tetramethoxydisiloxane.
［実施例２］１，３−ビス（メチルピペラジノプロピル）−１，１，３，３−テトラエトキシジシロキサンの合成
撹拌機、還流器、滴下ロート及び温度計を備えたフラスコに、クロロプロピルトリエトキシシラン７２２．６ｇ（３．００１モル）と水２７．１ｇ（１．５１モル）、メタンスルホン酸２．９ｇ（０．０３１モル）を仕込み、室温で１３時間撹拌した。反応液にナトリウムエチラートの２０質量％エタノール溶液１１．４ｇ（０．０３４４モル）を加えて３０分間撹拌した。次いで酢酸０．９ｇ（０．０２モル）を加えて３０分間撹拌した。得られた反応液を蒸留し、１５０℃／０．４ｋＰａの留分（１，３−ビス（クロロプロピル）−１，１，３，３−テトラエトキシジシロキサン）を１４２．８ｇ得た。
撹拌機、還流器、滴下ロート及び温度計を備えたフラスコに、メチルピペラジン６０．１ｇ（０．６００モル）とヘキサン６．０ｇ、Ｎ−メチルピロリドン６．０ｇを仕込み、１１０℃に加熱した。得られた反応液に、上記１，３−ビス（クロロプロピル）−１，１，３，３−テトラエトキシジシロキサン４０．８ｇ（０．１００モル）を１１０〜１２０℃の温度を保持しながら２時間かけて滴下し、同じ温度で更に５時間撹拌した。反応混合物を５０℃に冷却し、エチレンジアミン１８．０ｇ（０．３００モル）を加えて、同じ温度で３０分間撹拌した。生じたエチレンジアミン塩酸塩分液操作によって除去した後、上層にナトリウムエトキシドの２０質量％エタノール溶液を１．２ｇ（０．００３５モル）加えて更に酢酸０．２ｇ（０．００３モル）で逆中和した。得られた反応液を蒸留し、２１９℃／０．３ｋＰａの留分（１，３−ビス（メチルピペラジノプロピル）−１，１，３，３−テトラエトキシジシロキサン）を３６．１ｇ得た。
[Example 2] Synthesis of 1,3-bis (methylpiperazinopropyl) -1,1,3,3-tetraethoxydisiloxane Into a flask equipped with a stirrer, a refluxer, a dropping funnel and a thermometer, 722.6 g (3.001 mol) of propyltriethoxysilane, 27.1 g (1.51 mol) of water and 2.9 g (0.031 mol) of methanesulfonic acid were charged and stirred at room temperature for 13 hours. To the reaction solution, 11.4 g (0.0344 mol) of a 20 mass% ethanol solution of sodium ethylate was added and stirred for 30 minutes. Next, 0.9 g (0.02 mol) of acetic acid was added and stirred for 30 minutes. The obtained reaction liquid was distilled to obtain 142.8 g of a fraction (1,3-bis (chloropropyl) -1,1,3,3-tetraethoxydisiloxane) at 150 ° C./0.4 kPa.
A flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer was charged with 60.1 g (0.600 mol) of methylpiperazine, 6.0 g of hexane, and 6.0 g of N-methylpyrrolidone, and heated to 110 ° C. In the obtained reaction solution, 40.8 g (0.100 mol) of 1,3-bis (chloropropyl) -1,1,3,3-tetraethoxydisiloxane was maintained at a temperature of 110 to 120 ° C. The solution was added dropwise over 2 hours, and the mixture was further stirred at the same temperature for 5 hours. The reaction mixture was cooled to 50 ° C., 18.0 g (0.300 mol) of ethylenediamine was added, and the mixture was stirred at the same temperature for 30 minutes. After removing the resulting ethylenediamine hydrochloride by a liquid separation operation, 1.2 g (0.0035 mol) of a 20 mass% ethanol solution of sodium ethoxide was added to the upper layer, and reverse neutralization was further performed with 0.2 g (0.003 mol) of acetic acid. did. The obtained reaction solution was distilled to obtain 36.1 g of a fraction (1,3-bis (methylpiperazinopropyl) -1,1,3,3-tetraethoxydisiloxane) at 219 ° C./0.3 kPa. It was.
得られた留分の質量スペクトル、1Ｈ−ＮＭＲスペクトル、ＩＲスペクトルを測定した。
質量スペクトル
ｍ／ｚ ５３４ ４９０ ３７２ １１３
ＩＲスペクトル
図３にチャートで示す。
1Ｈ−ＮＭＲスペクトル（重クロロホルム溶媒）
図４にチャートで示す。
以上の結果より、得られた化合物は、１，３−ビス（メチルピペラジノプロピル）−１，１，３，３−テトラエトキシジシロキサンであることが確認された。
A mass spectrum, 1 H-NMR spectrum, and IR spectrum of the obtained fraction were measured.
Mass spectrum m / z 534 490 372 113
IR spectrum FIG. 3 is a chart.
1 H-NMR spectrum (deuterated chloroform solvent)
FIG. 4 shows a chart.
From the above results, it was confirmed that the obtained compound was 1,3-bis (methylpiperazinopropyl) -1,1,3,3-tetraethoxydisiloxane.
［実施例３、４及び比較例１］
エポキシ樹脂への添加実験
エポキシ樹脂（東京エポキシレジン製：ＪＥＲ−８２８）４０ｇに対し、上記実施例１で合成した１，３−ビス（ジエチルアミノプロピル）−１，１，３，３−テトラメトキシジシロキサン、上記実施例２で合成した１，３−ビス（メチルピペラジノプロピル）−１，１，３，３−テトラエトキシジシロキサン、又は１，３−ビス（アミノプロピル）−１，１，３，３−テトラメトキシジシロキサンを４．０ｇ加え、５分間室温で撹拌した。得られた混合物を室温で静置し、１２時間後の性状を確認した。性状の変化については、上記混合物を含む容器を４５度に傾け、５秒以内に内容物が流動するかを目視で確認した。５秒以内に内容物が流動した場合は流動性あり、変化が無かった場合は流動性なしと判断した。
[Examples 3 and 4 and Comparative Example 1]
Addition experiment to epoxy resin 1,3-bis (diethylaminopropyl) -1,1,3,3-tetramethoxydi synthesized in Example 1 above with respect to 40 g of epoxy resin (manufactured by Tokyo Epoxy Resin: JER-828) Siloxane, 1,3-bis (methylpiperazinopropyl) -1,1,3,3-tetraethoxydisiloxane synthesized in Example 2 above, or 1,3-bis (aminopropyl) -1,1, 4.0 g of 3,3-tetramethoxydisiloxane was added and stirred at room temperature for 5 minutes. The obtained mixture was allowed to stand at room temperature, and the properties after 12 hours were confirmed. Regarding changes in properties, the container containing the mixture was tilted at 45 degrees, and it was visually confirmed whether the contents would flow within 5 seconds. When the contents flowed within 5 seconds, it was judged that there was fluidity, and when there was no change, it was judged that there was no fluidity.
表１の結果から、本発明のアミノアルキルアルコキシジシロキサン化合物は、エポキシ樹脂に添加できることが確認された。 From the results in Table 1, it was confirmed that the aminoalkylalkoxydisiloxane compound of the present invention can be added to the epoxy resin.
Claims (3)
で示されるアミノアルキルアルコキシシラン化合物を加水分解縮合させることを特徴とする請求項１記載の一般式（１）で示されるアミノアルキルアルコキシジシロキサン化合物の製造方法。 The following general formula (2)
The method for producing an aminoalkylalkoxydisiloxane compound represented by the general formula (1) according to claim 1, wherein the aminoalkylalkoxysilane compound represented by formula (1) is hydrolytically condensed.
で示されるハロアルキルアルコキシジシロキサン化合物と、下記一般式（４）
で示されるアミン化合物を反応させることを特徴とする請求項１記載の一般式（１）で示されるアミノアルキルアルコキシジシロキサン化合物の製造方法。 The following general formula (3)
A haloalkylalkoxydisiloxane compound represented by the following general formula (4):
A process for producing an aminoalkylalkoxydisiloxane compound represented by the general formula (1) according to claim 1, wherein the amine compound represented by formula (1) is reacted.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015131630A JP6365445B2 (en) | 2015-06-30 | 2015-06-30 | Aminoalkylalkoxydisiloxane compound and method for producing the same |
| KR1020160079848A KR102341724B1 (en) | 2015-06-30 | 2016-06-27 | Aminoalkylalkoxydisiloxane compound and method for preparing the same |
| CN201610507105.5A CN106317099A (en) | 2015-06-30 | 2016-06-30 | Aminoalkylalkoxydisiloxane compound and method for preparing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015131630A JP6365445B2 (en) | 2015-06-30 | 2015-06-30 | Aminoalkylalkoxydisiloxane compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017014140A JP2017014140A (en) | 2017-01-19 |
| JP6365445B2 true JP6365445B2 (en) | 2018-08-01 |
Family
ID=57725833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015131630A Active JP6365445B2 (en) | 2015-06-30 | 2015-06-30 | Aminoalkylalkoxydisiloxane compound and method for producing the same |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP6365445B2 (en) |
| KR (1) | KR102341724B1 (en) |
| CN (1) | CN106317099A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102014521B1 (en) * | 2016-04-25 | 2019-10-21 | 주식회사 엘지화학 | Modified conjugated diene polymer and preparing method thereof |
| KR102288852B1 (en) * | 2018-05-25 | 2021-08-12 | 주식회사 엘지화학 | Modified conjugated diene polymer and rubber composition comprising the same |
| JP2021085025A (en) * | 2019-11-29 | 2021-06-03 | 株式会社ブリヂストン | Rubber composition and tire |
| WO2024106213A1 (en) * | 2022-11-17 | 2024-05-23 | 信越化学工業株式会社 | Method for producing disiloxane compound |
| CN115974911B (en) * | 2023-03-14 | 2023-06-02 | 北京奇点势能科技有限公司 | Sufex click chemistry amino silane coupling agent and preparation method and application thereof |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB786452A (en) * | 1954-09-10 | 1957-11-20 | Midland Silicones Ltd | Improvements in or relating to organosilicon compounds |
| US2814572A (en) * | 1955-08-17 | 1957-11-26 | Dow Corning | Organosilicon compounds and a method for waterproofing glass and product produced thereby |
| US2990230A (en) * | 1957-09-03 | 1961-06-27 | Dow Corning | Process of printing textiles and the composition employed therein |
| JPS5411953A (en) * | 1977-06-29 | 1979-01-29 | Shin Etsu Chem Co Ltd | Cold-curable organopolysiloxane composition |
| US4287326A (en) | 1980-03-03 | 1981-09-01 | Toray Silicone Company, Ltd. | Siloxane-modified epoxy resin compositions |
| JPS5718758A (en) * | 1980-07-08 | 1982-01-30 | Shin Etsu Chem Co Ltd | Organopolysiloxane composition curable at room temperature |
| JP2622729B2 (en) * | 1988-08-15 | 1997-06-18 | 旭電化工業株式会社 | Polymer material composition with improved light fastness |
| JPH05295219A (en) * | 1992-04-22 | 1993-11-09 | Mitsui Toatsu Chem Inc | Resin composition |
| JPH0732547A (en) * | 1993-07-16 | 1995-02-03 | Mitsui Toatsu Chem Inc | Heat resistant laminate |
| JPH10120690A (en) * | 1996-10-23 | 1998-05-12 | Japan Energy Corp | Novel quaternary imidazolium salt derivative and method for producing the same |
| DE19725501C1 (en) * | 1997-06-17 | 1998-12-10 | Huels Silicone Gmbh | Alkoxy crosslinking RTVl silicone rubber mixtures |
| JP3915875B2 (en) * | 2000-12-22 | 2007-05-16 | 信越化学工業株式会社 | Process for producing N-substituted-3-silylpropylamines and derivatives thereof |
| JP2003316000A (en) * | 2002-04-24 | 2003-11-06 | Toray Ind Inc | Photosensitive ceramic composition |
| CN1938364A (en) * | 2003-10-07 | 2007-03-28 | 克莱里安特财务(Bvi)有限公司 | Polysiloxanes with multiple quaternary ammonium group |
| JP4257515B2 (en) * | 2003-10-10 | 2009-04-22 | 信越化学工業株式会社 | Process for producing 1,3-bis (3-aminopropyl) -1,1,3,3-tetramethyldisiloxane |
| US20060269498A1 (en) * | 2005-05-17 | 2006-11-30 | Gerard Malle | Hair shaping composition comprising at least one polyguanidine other than hydroxide |
| US20060272107A1 (en) * | 2005-05-17 | 2006-12-07 | Gerard Malle | Hair relaxing composition comprising at least one non-hydroxide polyguanidine |
| DE102005039511A1 (en) * | 2005-08-20 | 2007-02-22 | Clariant Produkte (Deutschland) Gmbh | Use of quaternary polysiloxanes in cleaning and care products |
| RU2332422C2 (en) * | 2006-05-23 | 2008-08-27 | Ооо "Инстрой" | Application of organosilicone amine as multifunctional additive for foamed polyurethane compositions |
| JP5076405B2 (en) * | 2006-09-01 | 2012-11-21 | 東ソー株式会社 | Polyurethane resin production catalyst and polyurethane resin production method using the same |
| JP5745733B2 (en) * | 2006-10-25 | 2015-07-08 | Jsr株式会社 | Method for producing modified polymer, modified polymer obtained by the method and rubber composition thereof |
| JP2008111023A (en) * | 2006-10-30 | 2008-05-15 | Shin Etsu Chem Co Ltd | Aqueous solution containing propylsilanol compound having tertiary amino group |
| JP4803381B2 (en) * | 2006-12-12 | 2011-10-26 | 信越化学工業株式会社 | Method for producing aminoalkylsilane compound |
| JP5057064B2 (en) * | 2007-12-18 | 2012-10-24 | 信越化学工業株式会社 | Process for producing alkylpiperazinoalkylsilane compounds |
| JP5316300B2 (en) * | 2009-08-07 | 2013-10-16 | 信越化学工業株式会社 | Abrasion resistant silicone coating composition, coated article and method for producing the same |
| JP5302918B2 (en) * | 2010-03-10 | 2013-10-02 | 独立行政法人科学技術振興機構 | Method for producing diaminonitrile analogue |
| JP5900399B2 (en) * | 2013-03-27 | 2016-04-06 | 信越化学工業株式会社 | Bis (aminoalkyl) silane compound and method for producing the same |
-
2015
- 2015-06-30 JP JP2015131630A patent/JP6365445B2/en active Active
-
2016
- 2016-06-27 KR KR1020160079848A patent/KR102341724B1/en active IP Right Grant
- 2016-06-30 CN CN201610507105.5A patent/CN106317099A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN106317099A (en) | 2017-01-11 |
| JP2017014140A (en) | 2017-01-19 |
| KR102341724B1 (en) | 2021-12-24 |
| KR20170003417A (en) | 2017-01-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6365445B2 (en) | Aminoalkylalkoxydisiloxane compound and method for producing the same | |
| JP2011121906A (en) | Silane compound containing two or more amino groups and method for producing the same | |
| JP5494233B2 (en) | Cyclic silazane compound having carboxylic acid ester group and method for producing the same | |
| JP5153635B2 (en) | Novel epoxy compound and method for producing the same | |
| JP2012516296A (en) | Process for producing bis- and tris (silylorgano) amine | |
| JP2020176195A (en) | Bissilylamino group-containing organic polysilazane compound, method for producing the same, composition containing the same, and cured product | |
| KR101803591B1 (en) | Organoxysilane compounds having silyl-protected secondary amino group and making method | |
| JP4948813B2 (en) | Method for producing ketimine structure-containing alkoxysilane | |
| JP6052140B2 (en) | Organoxysilane compound having bissilylamino group and process for producing the same | |
| JP6303982B2 (en) | Novel bisalkoxyaminosilane compound and production method thereof | |
| JP6947084B2 (en) | Method for Producing Imine Structure-Containing Organoxysilane Compound | |
| US7402648B2 (en) | Method for producing cyclic organic silicon compound and organic silicon resin having alcoholic hydroxyl group | |
| WO2024106212A1 (en) | Composition containing aminoalkyl alkoxy disiloxane compound and aminoalkyl alkoxy oligosiloxane compound, and method for producing same | |
| JP6003856B2 (en) | Terminally modified silacyclobutane ring-opening polymer and process for producing the same | |
| US11312734B2 (en) | Nitrogen-containing cyclic organoxysilane compound and method for producing the same | |
| JP6237564B2 (en) | Organooxy compound and method for producing the same | |
| JP6720913B2 (en) | Unsaturated bond-containing bissilyl compound and method for producing the same | |
| EP4410796A1 (en) | Method for producing alkoxysilyl alkylaminopropyl-modified polysiloxane compound | |
| JP2013256477A (en) | Method for producing organoxysilane compound having piperazinyl group and piperazine compound | |
| JP5052209B2 (en) | Novel epoxy compound and method for producing the same | |
| JP2002012597A (en) | Organic silicon compound | |
| JP6319122B2 (en) | Sulfur-containing aminoorganoxysilane compound and method for producing the same | |
| JP5644515B2 (en) | Unsaturated bond-containing silyl group-protected amino acid compound and method for producing the same | |
| JP4055429B2 (en) | Fluorine-containing organosilicon compound | |
| JPS6356231B2 (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170525 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20180222 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180227 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180427 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20180605 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20180618 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 6365445 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |