JP4870567B2 - 多面シルセスキオキサンの簡便な合成及びその使用 - Google Patents
多面シルセスキオキサンの簡便な合成及びその使用 Download PDFInfo
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- JP4870567B2 JP4870567B2 JP2006536892A JP2006536892A JP4870567B2 JP 4870567 B2 JP4870567 B2 JP 4870567B2 JP 2006536892 A JP2006536892 A JP 2006536892A JP 2006536892 A JP2006536892 A JP 2006536892A JP 4870567 B2 JP4870567 B2 JP 4870567B2
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- silsesquioxane
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- 230000015572 biosynthetic process Effects 0.000 title description 21
- 238000003786 synthesis reaction Methods 0.000 title description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 45
- 150000001450 anions Chemical class 0.000 claims abstract description 39
- 125000000524 functional group Chemical group 0.000 claims abstract description 20
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 19
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 8
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 8
- 239000011368 organic material Substances 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 22
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- POPVULPQMGGUMJ-UHFFFAOYSA-N octasilsesquioxane cage Chemical compound O1[SiH](O[SiH](O2)O[SiH](O3)O4)O[SiH]4O[SiH]4O[SiH]1O[SiH]2O[SiH]3O4 POPVULPQMGGUMJ-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000003729 cation exchange resin Substances 0.000 claims description 9
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 6
- 238000002485 combustion reaction Methods 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 150000001367 organochlorosilanes Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 74
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 30
- -1 polysiloxanes Polymers 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 20
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 abstract description 18
- 239000005046 Chlorosilane Substances 0.000 abstract description 17
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract description 15
- 235000019253 formic acid Nutrition 0.000 abstract description 15
- 239000003456 ion exchange resin Substances 0.000 abstract description 5
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 5
- 150000007524 organic acids Chemical class 0.000 abstract description 5
- 235000005985 organic acids Nutrition 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 229920001296 polysiloxane Polymers 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 41
- 239000000047 product Substances 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002956 ash Substances 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 241000209094 Oryza Species 0.000 description 10
- 235000007164 Oryza sativa Nutrition 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
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- 230000035484 reaction time Effects 0.000 description 10
- 235000009566 rice Nutrition 0.000 description 10
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229920001429 chelating resin Polymers 0.000 description 8
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 239000010903 husk Substances 0.000 description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 5
- 239000012454 non-polar solvent Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000002516 radical scavenger Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229940075419 choline hydroxide Drugs 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- XUKFPAQLGOOCNJ-UHFFFAOYSA-N dimethyl(trimethylsilyloxy)silicon Chemical compound C[Si](C)O[Si](C)(C)C XUKFPAQLGOOCNJ-UHFFFAOYSA-N 0.000 description 3
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
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- 229920005989 resin Polymers 0.000 description 3
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- 238000000926 separation method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- 239000005051 trimethylchlorosilane Substances 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910003902 SiCl 4 Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
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- MRRXLWNSVYPSRB-UHFFFAOYSA-N ethenyl-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)C=C MRRXLWNSVYPSRB-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical group COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 238000005133 29Si NMR spectroscopy Methods 0.000 description 1
- ZDXJSOXLVCWEQZ-UHFFFAOYSA-N 6,6,6-trifluorohex-1-ene Chemical compound FC(F)(F)CCCC=C ZDXJSOXLVCWEQZ-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
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- 229910018540 Si C Inorganic materials 0.000 description 1
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- 239000004115 Sodium Silicate Substances 0.000 description 1
- AAGGQHFQJFTHCM-UHFFFAOYSA-N [chloro(dimethyl)silyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)O[Si](C)(C)Cl AAGGQHFQJFTHCM-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- ZIXLDMFVRPABBX-UHFFFAOYSA-N alpha-methylcyclopentanone Natural products CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 1
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- 238000010923 batch production Methods 0.000 description 1
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- VQPFDLRNOCQMSN-UHFFFAOYSA-N bromosilane Chemical compound Br[SiH3] VQPFDLRNOCQMSN-UHFFFAOYSA-N 0.000 description 1
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- RELBGMCPNQNKGH-UHFFFAOYSA-N chloro-phenyl-prop-2-enylsilane Chemical compound Cl[SiH](CC=C)c1ccccc1 RELBGMCPNQNKGH-UHFFFAOYSA-N 0.000 description 1
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- CVAGYCLEIYGJQT-UHFFFAOYSA-N dichloro(dioctyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)CCCCCCCC CVAGYCLEIYGJQT-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
- 239000010908 plant waste Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012451 post-reaction mixture Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 239000010876 untreated wood Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- 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
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/02—Polysilicates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/15—Impregnating involving polymerisation including use of polymer-containing impregnating agents
- B27K3/153—Without in-situ polymerisation, condensation, or cross-linking reactions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Silicon Polymers (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Description
ここに驚いたことに、シリカ含有自然有機生産物の燃焼又は熱分解からのシリカに富む副生成物は、多面シルセスキオキサンアニオンの合成のための低コストの出発原料として働くことが出来ることが発見された。更には、反応時間の大幅な短縮及び官能化多面シルセスキオキサン誘導体の向上した収率は、水不混和性の溶媒中で生じることが発見された。驚いたことに、この生成物はシルセスキオキサンケージの破壊を受けることなく、イオン交換樹脂の存在下で官能基交換によって他の官能化誘導体へ転化出来る。
本発明に使用する好適なシリカ源は、作物残査、石炭、コークス及びその類似物のようなシリカ含有有機物質からの燃焼又は熱分解残留物が挙げられる。最も好ましくは、その源はもみ殻灰又はフライアッシュである。
粉砕もみ殻灰(60.491g、0.998モル)、n−ブタノール(300mL、3.28モル)及び水(72.0mL、4.00モル)を収容したマグネティックスターラー付き1000mL丸底フラスコに、45%の水酸化コリンメタノール溶液(9218mL、1.70モル)を注ぎ入れる。また、反応容器に冷却器を取り付け、窒素でフラッシングする。反応混合物を100℃に8〜12時間加熱する。暗褐色のオクタアニオン溶液を残留もみ殻灰の濃厚スラリーからセライトを用いてろ過する。次いで、残留もみ殻灰をメタノール(約30mL)で数回洗浄する。冷却時にオクタアニオンのコリン塩の白い結晶が生成する。固体結晶を溶液からろ過し、空気中で乾燥させ、熱水から再結晶させることができる。以下に記載するようにSi8O20[Si(CH3)3]8に変換することにより、収量を決定する。合成は最適化されていない。
典型的な反応を以下のように実施する。固体(2−ヒドロキシエチル)トリメチルアンモニウムシリケートを上記のように製造し、次いで1mLのメタノールに溶解する。Si8O20 8−は、メタノール溶液(SiO2濃度1.38mol/L)中に見い出される唯一のシリケートアニオンであり、製造後7日経っても溶液状態で安定である。従って、溶液中のSi8O208−からSi8O20[Si(CH3)2H]8を製造するのに必要なジメチルクロロシランの化学量論的量は0.49mLと算出される。
典型的な反応は次のように実施される。Si8O20[Si(CH3)3]8(9.45mg)を1,1,3,3,−テトラメチルジシロキサン(6.5mL)中に溶解させ、次いで、アンバーライト15陽イオン交換樹脂(0.15g)を加える。Si8O20[Si(CH3)3]8の1,1,3,3,−テトラメチルジシロキサン溶液を雰囲気圧下で、室温で26時間激しく攪拌する。
Si8O20[Si(CH3)3]8は、室温でアンバーライト15陽イオン交換樹脂の存在下に、1100のVDMS/TMS比(1,3−ジビニル−1,1,3,3−テトラメチルジシロキサン中のビニルジメチルシリル基の数対Si8O20[Si(CH3)3]8中のトリメチルシリル基の数の比率)で、1,3−ジビニル−1,1,3,3−テトラメチルジシロキサンと反応させることが出来、たとえ反応時間が100時間まで延長されても、Si8O20[Si(CH3)2(CH=CH2)]7[Si(CH3)3]は、Si8O20[Si(CH3)2(CH=CH2)]8と共に存在する。ガスクロマトグラフィーを用いて反応を追跡することによって、Si8O20[Si(CH3)2(CH=CH2)]8の生成についての反応率は、約50時間後に遅くなることが分かる。加えて、ヘキサメチルジシロキサン及びビニルペンタメチルジシロキサンは、反応の間、副生成物として生成することが分かる。
500mLフラスコに250mLのオクタアニオン−水酸化テトラメチルアンモニウム−メタノール溶液、及びそれぞれ、長さ7.5cm、直径1cmの3つの松材試料を加えた。試料を加えた溶液を18時間還流した。木材試料を溶液から取り出し、そして100℃で24時間乾燥して、吸収メタノールを除去した。重量増加は木材試料当たり10%(平均0.3g)である。このようにして処理した試料は、プロパンガストーチにあてると燃焼するがトーチを取り除いた後燃焼は止むのに対して、未処理の木片は、燃焼し続ける。
Claims (4)
- 官能化シルセスキオキサンの製造方法において、
a1)天然産出の有機物質の燃焼から誘導されるシリカ源を提供するステップと、60℃を超えた温度下、アルコール溶媒中で前記シリカ源を水及び水酸化第4アンモニウムと反応させるステップと、を具える方法によって、式SiO5n−2 n−のアニオンを含む多面シルセスキオキサンの第4アンモニウム塩を提供するステップと;
a2)前記第4アンモニウム塩を1種又はそれ以上のオルガノクロロシランと液体中で反応させて、第1シロキシ官能基を有する多面シルセスキオキサンを提供するステップと;
b)合成陽イオン交換樹脂の存在下で、溶媒中の前記第1シロキシ官能基を有する多面シルセスキオキサンを第2官能基のシロキシ基を含有するジシロキサンと接触させるステップと;
c)第2シロキシ官能基を含有するシルセスキオキサンを単離するステップと;
を具えることを特徴とする製造方法。 - 前記溶媒が、第2官能基のシロキシ基を含有する前記ジシロキサンを具えることを特徴とする請求項1に記載の方法。
- 第1シロキシ官能基を有する前記シルセスキオキサンがオクタキス[トリメチルシロキシ]オクタシルセスキオキサンを具えることを特徴とする請求項1に記載の方法。
- 第2官能基の前記シロキシ基を含有する前記ジシロキサンが、Si−ビニル基、Si−アリル基、Si−H基、又はSi−エポキシ基を含有するジシロキサンを具えることを特徴とする請求項1に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US51366503P | 2003-10-23 | 2003-10-23 | |
US60/513,665 | 2003-10-23 | ||
US10/971,809 US7576169B2 (en) | 2003-10-23 | 2004-10-22 | Facile synthesis of polyhedral silsesquioxane anions and use thereof |
US10/971,809 | 2004-10-22 | ||
PCT/US2004/035314 WO2005039744A2 (en) | 2003-10-23 | 2004-10-25 | Facile synthesis of polyhedral silsesquioxane anions and use thereof |
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JP2007509177A JP2007509177A (ja) | 2007-04-12 |
JP4870567B2 true JP4870567B2 (ja) | 2012-02-08 |
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JP2006536892A Expired - Fee Related JP4870567B2 (ja) | 2003-10-23 | 2004-10-25 | 多面シルセスキオキサンの簡便な合成及びその使用 |
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US (1) | US7576169B2 (ja) |
EP (1) | EP1675671A4 (ja) |
JP (1) | JP4870567B2 (ja) |
AU (1) | AU2004283733B2 (ja) |
CA (1) | CA2543109C (ja) |
MX (1) | MXPA06004491A (ja) |
WO (1) | WO2005039744A2 (ja) |
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US7265194B1 (en) * | 2003-10-16 | 2007-09-04 | Hybrid Plastics Inc. | Polyhedral oligomeric silsesquinoxanes and polyhedral oligomeric silicates bearing surfactant functionalities |
US7915369B2 (en) * | 2004-12-07 | 2011-03-29 | Panasonic Electric Works Co., Ltd. | Ultraviolet transmissive polyhedral silsesquioxane polymers |
US7868198B2 (en) * | 2007-06-15 | 2011-01-11 | Laine Richard M | Multi-functional silsesquioxanes for novel coating applications |
WO2009002660A2 (en) * | 2007-06-15 | 2008-12-31 | Mayaterials, Inc. | Multi-functional silsesquioxanes for novel coating applications |
WO2009064745A1 (en) * | 2007-11-13 | 2009-05-22 | Sachem, Inc. | High negative zeta potential polyhedral silsesquioxane composition and method for damage free semiconductor wet clean |
DE102009045669A1 (de) * | 2009-10-14 | 2011-04-21 | Wacker Chemie Ag | Verfahren zur Herstellung von Organooligosilsesquioxanen |
US8916645B2 (en) * | 2010-01-19 | 2014-12-23 | Michigan Molecular Institute | Hyperbranched polymers containing polyhedral oligosilsequioxane branching units |
JP2012176909A (ja) * | 2011-02-25 | 2012-09-13 | Epia:Kk | 水溶性有機珪素の抽出方法及び抽出装置 |
GB201201357D0 (en) * | 2012-01-27 | 2012-03-14 | Univ Leuven Kath | Poly oligosiloxysilane |
CN102699965A (zh) * | 2012-06-15 | 2012-10-03 | 辽宁美联复合材料有限公司 | 一种纳米改性木材的制备方法 |
CA2884906C (en) | 2014-03-12 | 2023-04-04 | Paul M. Zelisko | Siloxane-containing hybrid materials |
CA2941124C (en) * | 2014-04-01 | 2018-10-16 | Halliburton Energy Services, Inc. | Organic water scavenging additives for use in drilling fluids |
US10584186B2 (en) | 2015-07-22 | 2020-03-10 | Bridgestone Corporation | Silane-functionalized polymer and process for making and using same |
CN109651616A (zh) * | 2017-10-12 | 2019-04-19 | 弗洛里光电材料(苏州)有限公司 | 含多个硅烷基苯基的poss纳米杂化分子化合物及应用 |
CN113087907B (zh) * | 2019-12-23 | 2023-01-13 | 万华化学集团股份有限公司 | 一种硅醇锂及其制备方法和应用 |
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JPH06329687A (ja) * | 1993-05-13 | 1994-11-29 | Wacker Chemie Gmbh | 有機ケイ素化合物及びその製法 |
WO2002100867A1 (en) * | 2000-10-27 | 2002-12-19 | The Regents Of The University Of Michigan | Well-defined nanosized building blocks for organic/inorganic nanocomposites |
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DE3837397A1 (de) * | 1988-11-03 | 1990-05-10 | Wacker Chemie Gmbh | Neue organooligosilsesquioxane |
US5330734A (en) | 1993-03-09 | 1994-07-19 | Exxon Research And Engineering Company | Silica pillared micas |
US6288257B1 (en) * | 1999-08-20 | 2001-09-11 | General Electric Company | Method for making tetraorganooxysilanes |
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- 2004-10-22 US US10/971,809 patent/US7576169B2/en not_active Expired - Fee Related
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JPH06329687A (ja) * | 1993-05-13 | 1994-11-29 | Wacker Chemie Gmbh | 有機ケイ素化合物及びその製法 |
WO2002100867A1 (en) * | 2000-10-27 | 2002-12-19 | The Regents Of The University Of Michigan | Well-defined nanosized building blocks for organic/inorganic nanocomposites |
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AU2004283733B2 (en) | 2010-01-21 |
WO2005039744A2 (en) | 2005-05-06 |
JP2007509177A (ja) | 2007-04-12 |
EP1675671A4 (en) | 2012-01-18 |
US20050142054A1 (en) | 2005-06-30 |
MXPA06004491A (es) | 2006-06-27 |
AU2004283733A1 (en) | 2005-05-06 |
EP1675671A2 (en) | 2006-07-05 |
WO2005039744A3 (en) | 2005-12-29 |
US7576169B2 (en) | 2009-08-18 |
CA2543109C (en) | 2011-06-14 |
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