JP6329764B2 - 対称ハイパーブランチ型シリコーン変性重合性化合物、及びそのモジュール化した製造方法 - Google Patents
対称ハイパーブランチ型シリコーン変性重合性化合物、及びそのモジュール化した製造方法 Download PDFInfo
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- JP6329764B2 JP6329764B2 JP2013266503A JP2013266503A JP6329764B2 JP 6329764 B2 JP6329764 B2 JP 6329764B2 JP 2013266503 A JP2013266503 A JP 2013266503A JP 2013266503 A JP2013266503 A JP 2013266503A JP 6329764 B2 JP6329764 B2 JP 6329764B2
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- 150000001875 compounds Chemical class 0.000 title claims description 86
- 238000004519 manufacturing process Methods 0.000 title claims description 32
- -1 hydroxycarbonyl group Chemical group 0.000 claims description 65
- 239000003054 catalyst Substances 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000000524 functional group Chemical group 0.000 claims description 38
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000005647 linker group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 229910052693 Europium Inorganic materials 0.000 claims description 13
- 229910052772 Samarium Inorganic materials 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 229910052746 lanthanum Inorganic materials 0.000 claims description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
- 229910052727 yttrium Inorganic materials 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 229910052706 scandium Inorganic materials 0.000 claims description 12
- 239000011701 zinc Substances 0.000 claims description 12
- 229910052725 zinc Inorganic materials 0.000 claims description 12
- 229910052726 zirconium Inorganic materials 0.000 claims description 12
- 229910052684 Cerium Inorganic materials 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052738 indium Inorganic materials 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 10
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 9
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 8
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 8
- 125000005641 methacryl group Chemical group 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 150000001993 dienes Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 150000004698 iron complex Chemical class 0.000 claims description 6
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 6
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ketene group Chemical group C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 6
- 125000005504 styryl group Chemical group 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 6
- 150000003624 transition metals Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000007530 organic bases Chemical group 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 150000004699 copper complex Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004069 aziridinyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000004999 nitroaryl group Chemical group 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 230000006315 carbonylation Effects 0.000 claims description 2
- 238000005810 carbonylation reaction Methods 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims 2
- 150000001502 aryl halides Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 60
- 238000003786 synthesis reaction Methods 0.000 description 58
- 239000000047 product Substances 0.000 description 45
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 24
- 238000004566 IR spectroscopy Methods 0.000 description 23
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 21
- 230000008707 rearrangement Effects 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 19
- 238000004611 spectroscopical analysis Methods 0.000 description 19
- 150000001336 alkenes Chemical class 0.000 description 16
- 229920001296 polysiloxane Polymers 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 13
- 229910052710 silicon Inorganic materials 0.000 description 13
- 239000010703 silicon Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 210000000080 chela (arthropods) Anatomy 0.000 description 12
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 12
- 238000009826 distribution Methods 0.000 description 12
- 229960002179 ephedrine Drugs 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- 230000009257 reactivity Effects 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 8
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 229910052742 iron Inorganic materials 0.000 description 7
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 4
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
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- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 4
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 4
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 4
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- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
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- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 4
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
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- 235000019645 odor Nutrition 0.000 description 4
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- DEDZSLCZHWTGOR-UHFFFAOYSA-N propylcyclohexane Chemical compound CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- OFLGYLDXUIXHQY-UHFFFAOYSA-N 1,3-bis(prop-2-enoxy)propan-2-ol Chemical compound C=CCOCC(O)COCC=C OFLGYLDXUIXHQY-UHFFFAOYSA-N 0.000 description 3
- ZKJNETINGMOHJG-UHFFFAOYSA-N 1-prop-1-enoxyprop-1-ene Chemical group CC=COC=CC ZKJNETINGMOHJG-UHFFFAOYSA-N 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
- 101150065749 Churc1 gene Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 3
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- IESWIBSMHJCJAG-UHFFFAOYSA-L dibutyltin(2+);8-methyl-2-(6-methylheptyl)-2-sulfanylnonanoate Chemical compound CCCC[Sn+2]CCCC.CC(C)CCCCCC(S)(C([O-])=O)CCCCCC(C)C.CC(C)CCCCCC(S)(C([O-])=O)CCCCCC(C)C IESWIBSMHJCJAG-UHFFFAOYSA-L 0.000 description 1
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- NTQNGHFYRXWUMB-UHFFFAOYSA-N ethane-1,2-diamine;europium Chemical compound [Eu].NCCN NTQNGHFYRXWUMB-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- TWNOVENTEPVGEJ-UHFFFAOYSA-K europium(3+);trifluoromethanesulfonate Chemical compound [Eu+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F TWNOVENTEPVGEJ-UHFFFAOYSA-K 0.000 description 1
- NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- UFULDTPDHIRNGS-UHFFFAOYSA-N hept-6-en-1-ol Chemical compound OCCCCCC=C UFULDTPDHIRNGS-UHFFFAOYSA-N 0.000 description 1
- GEAWFZNTIFJMHR-UHFFFAOYSA-N hepta-1,6-diene Chemical compound C=CCCCC=C GEAWFZNTIFJMHR-UHFFFAOYSA-N 0.000 description 1
- VPFMEXRVUOPYRG-UHFFFAOYSA-N hex-5-ynoic acid Chemical compound OC(=O)CCCC#C VPFMEXRVUOPYRG-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- SKWCWFYBFZIXHE-UHFFFAOYSA-K indium acetylacetonate Chemical compound CC(=O)C=C(C)O[In](OC(C)=CC(C)=O)OC(C)=CC(C)=O SKWCWFYBFZIXHE-UHFFFAOYSA-K 0.000 description 1
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 1
- OLVUQXVYJYMARU-UHFFFAOYSA-N indium;pyridine Chemical compound [In].C1=CC=NC=C1 OLVUQXVYJYMARU-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical group 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 229940087654 iron carbonyl Drugs 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- PGJLOGNVZGRMGX-UHFFFAOYSA-L iron(2+);trifluoromethanesulfonate Chemical compound [Fe+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F PGJLOGNVZGRMGX-UHFFFAOYSA-L 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- WHJXGGISJBFSJJ-UHFFFAOYSA-N iron;pyridine Chemical compound [Fe].C1=CC=NC=C1 WHJXGGISJBFSJJ-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- JLRJWBUSTKIQQH-UHFFFAOYSA-K lanthanum(3+);triacetate Chemical compound [La+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JLRJWBUSTKIQQH-UHFFFAOYSA-K 0.000 description 1
- WGJJZRVGLPOKQT-UHFFFAOYSA-K lanthanum(3+);trifluoromethanesulfonate Chemical compound [La+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WGJJZRVGLPOKQT-UHFFFAOYSA-K 0.000 description 1
- XKUYOJZZLGFZTC-UHFFFAOYSA-K lanthanum(iii) bromide Chemical compound Br[La](Br)Br XKUYOJZZLGFZTC-UHFFFAOYSA-K 0.000 description 1
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 1
- AIZZRJZXSDOBGH-UHFFFAOYSA-N lanthanum;pyridine Chemical compound [La].C1=CC=NC=C1 AIZZRJZXSDOBGH-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000003328 mesylation reaction Methods 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 1
- AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- NFSAPTWLWWYADB-UHFFFAOYSA-N n,n-dimethyl-1-phenylethane-1,2-diamine Chemical compound CN(C)C(CN)C1=CC=CC=C1 NFSAPTWLWWYADB-UHFFFAOYSA-N 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-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
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- IFYYERYAOQBKQI-UHFFFAOYSA-N octanal;platinum Chemical compound [Pt].CCCCCCCC=O IFYYERYAOQBKQI-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 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 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- ZQBVUULQVWCGDQ-UHFFFAOYSA-N propan-1-ol;propan-2-ol Chemical compound CCCO.CC(C)O ZQBVUULQVWCGDQ-UHFFFAOYSA-N 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ROJNQEKBKQHPAP-UHFFFAOYSA-N pyridine;samarium Chemical compound [Sm].C1=CC=NC=C1 ROJNQEKBKQHPAP-UHFFFAOYSA-N 0.000 description 1
- YVCHGFCEBMODFR-UHFFFAOYSA-N pyridine;scandium Chemical compound [Sc].C1=CC=NC=C1 YVCHGFCEBMODFR-UHFFFAOYSA-N 0.000 description 1
- RJFJFTPCYCPBAR-UHFFFAOYSA-N pyridine;silicon Chemical compound [Si].C1=CC=NC=C1 RJFJFTPCYCPBAR-UHFFFAOYSA-N 0.000 description 1
- ONBVQKRJJFWQCL-UHFFFAOYSA-N pyridine;yttrium Chemical compound [Y].C1=CC=NC=C1 ONBVQKRJJFWQCL-UHFFFAOYSA-N 0.000 description 1
- NQWKBTTYOHAFRL-UHFFFAOYSA-N pyridine;zirconium Chemical compound [Zr].C1=CC=NC=C1 NQWKBTTYOHAFRL-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- JPDBEEUPLFWHAJ-UHFFFAOYSA-K samarium(3+);triacetate Chemical compound [Sm+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JPDBEEUPLFWHAJ-UHFFFAOYSA-K 0.000 description 1
- ICKYUJFKBKOPJT-UHFFFAOYSA-K samarium(3+);tribromide Chemical compound Br[Sm](Br)Br ICKYUJFKBKOPJT-UHFFFAOYSA-K 0.000 description 1
- DDCWGUIPLGMBPO-UHFFFAOYSA-K samarium(3+);trifluoromethanesulfonate Chemical compound [Sm+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F DDCWGUIPLGMBPO-UHFFFAOYSA-K 0.000 description 1
- BHXBZLPMVFUQBQ-UHFFFAOYSA-K samarium(iii) chloride Chemical compound Cl[Sm](Cl)Cl BHXBZLPMVFUQBQ-UHFFFAOYSA-K 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- APPHYFNIXVIIJR-UHFFFAOYSA-K scandium bromide Chemical compound Br[Sc](Br)Br APPHYFNIXVIIJR-UHFFFAOYSA-K 0.000 description 1
- DVMZCYSFPFUKKE-UHFFFAOYSA-K scandium chloride Chemical compound Cl[Sc](Cl)Cl DVMZCYSFPFUKKE-UHFFFAOYSA-K 0.000 description 1
- DBTMQFKUVICLQN-UHFFFAOYSA-K scandium(3+);triacetate Chemical compound [Sc+3].CC([O-])=O.CC([O-])=O.CC([O-])=O DBTMQFKUVICLQN-UHFFFAOYSA-K 0.000 description 1
- NYMLCLICEBTBKR-UHFFFAOYSA-H scandium(3+);tricarbonate Chemical compound [Sc+3].[Sc+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O NYMLCLICEBTBKR-UHFFFAOYSA-H 0.000 description 1
- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- XFBUYKFQWJKKCV-UHFFFAOYSA-J silicon(4+) trifluoromethanesulfonate Chemical compound [Si+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F XFBUYKFQWJKKCV-UHFFFAOYSA-J 0.000 description 1
- JXJTWJYTKGINRZ-UHFFFAOYSA-J silicon(4+);tetraacetate Chemical compound [Si+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O JXJTWJYTKGINRZ-UHFFFAOYSA-J 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- JPJIEXKLJOWQQK-UHFFFAOYSA-K trifluoromethanesulfonate;yttrium(3+) Chemical compound [Y+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JPJIEXKLJOWQQK-UHFFFAOYSA-K 0.000 description 1
- WJPWYVWFKYPSJS-UHFFFAOYSA-J trifluoromethanesulfonate;zirconium(4+) Chemical compound [Zr+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WJPWYVWFKYPSJS-UHFFFAOYSA-J 0.000 description 1
- XQKBFQXWZCFNFF-UHFFFAOYSA-K triiodosamarium Chemical compound I[Sm](I)I XQKBFQXWZCFNFF-UHFFFAOYSA-K 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical group C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940105965 yttrium bromide Drugs 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
- WWOFRRCIVMFEDS-UHFFFAOYSA-N zinc;pyridine Chemical compound [Zn+2].C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1 WWOFRRCIVMFEDS-UHFFFAOYSA-N 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 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
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
下記一般式(1)で示される化合物を含有する対称ハイパーブランチ型シリコーン変性重合性化合物を提供する。
(RARB)2CHORC cRD (1)
(式中、RAは1価の直鎖、分岐又は環状のシロキサン鎖である。RBは−CH2CRb1Rb2(CRb3Rb4)n1OCH2−で示され、Rb1、Rb2、Rb3、及びRb4がそれぞれ同一でも異なっていても良い水素原子又は互いに結合しても良い炭素数1〜10の直鎖、分岐又は環状の炭化水素基である2価のハイドロカルボニレンメチレンエーテル基、n1は0〜10から選択される整数である。RCは2価の連結基、cは0又は1である。RDは不飽和の重合性官能基である。)
(式中、Xは−CH2−、−C(=O)−、及び−C(=S)−から選択されるいずれかであり、RYは窒素原子、酸素原子、硫黄原子、又は炭素原子から選択されるいずれかの原子を0個又は1個含む2価の官能基であり、RZは酸素原子で置換してもよい炭素数2〜10の直鎖、分岐又は環状のアルキレン基で、yは0又は1から選択される整数であり、RZ’とRZ”はそれぞれ炭素数1〜10のアルキル基である。)
前記一般式(1)で示される化合物を、下記一般式(2)で示される中間体と不飽和の重合性官能基を有する化合物とを反応させることにより製造するモジュール化した製造方法を提供する。
(RARB)2CHOH (2)
(式中、RA、RBは前記と同様である。)
RA’ (3)
(式中、RA’は分子中に一つ反応性水素を持つ直鎖、分岐又は環状のシロキサンである。以降、H−シロキサンと略す場合もある。)
RB’ 2CHOH (4)
(式中、RB’はCH2=CRb1(CRb3Rb4)n1’OCH2−で示される末端に二重結合を持つ1価のハイドロカルボニレンメチレンエーテル基であり、Rb1、Rb3、及びRb4は前記と同様であり、n1’は0〜10から選択される整数である。)
RD’ (5)
(式中、RD’は反応性官能基を持つ不飽和の重合性化合物である。)
RC’RD (6)
(式中、RDは前記と同様であり、RC’は、1価の反応性基である。)
(式中、X、RY、RZ、y、RZ’、及びRZ”は前記と同様であり、RY’は窒素原子、酸素原子、硫黄原子、及び炭素原子から選択されるいずれかの原子を0個又は1個含む3価の官能基、Tは水酸基、塩素原子、及び臭素原子から選択されるいずれかの原子である。)
下記一般式(1)で示される化合物を含有する対称ハイパーブランチ型シリコーン変性重合性化合物(以後HBシリコーンと略すこともある)である。
(RARB)2CHORC cRD (1)
(式中、RAは1価の直鎖、分岐又は環状のシロキサン鎖である。RBは−CH2CRb1Rb2(CRb3Rb4)n1OCH2−で示され、Rb1、Rb2、Rb3、及びRb4がそれぞれ同一でも異なっていても良い水素原子又は互いに結合しても良い炭素数1〜10の直鎖、分岐又は環状の炭化水素基である2価のハイドロカルボニレンメチレンエーテル基、n1は0〜10から選択される整数である。RCは2価の連結基、cは0又は1である。RDは不飽和の重合性官能基である。)
(式中、Xは−CH2−、−C(=O)−、及び−C(=S)−から選択されるいずれかであり、RYは窒素原子、酸素原子、硫黄原子、又は炭素原子から選択されるいずれかの原子を0個又は1個含む2価の官能基であり、RZは酸素原子で置換してもよい炭素数2〜10の直鎖、分岐又は環状のアルキレン基で、yは0又は1から選択される整数であり、RZ’とRZ”はそれぞれ炭素数1〜10のアルキル基である。)
前記一般式(1)で示される化合物を、下記一般式(2)で示される中間体と不飽和の重合性官能基を有する化合物とを反応させることにより製造するモジュール化した製造方法で製造することが好ましい。
(RARB)2CHOH (2)
(式中、RA、RBは前記と同様である。)
前記一般式(1)で示される化合物は2段階の方法で製造することが好ましい。
前記一般式(2)で示される中間体は、下記一般式(3)で示される化合物と下記一般式(4)で示される化合物とをヒドロシリル化反応させることにより製造することが好ましい。
RA’ (3)
(式中、RA’は分子中に一つの反応性水素を持つ直鎖、分岐又は環状のシロキサンである。)
RB’ 2CHOH (4)
(式中、RB’はCH2=CRb1(CRb3Rb4)n1’OCH2−で示される末端に二重結合を持つ1価のハイドロカルボニレンメチレンエーテル基であり、Rb1、Rb3、及びRb4は前記と同様であり、n1’は0〜10から選択される整数である。)
不飽和の重合性官能基を有する化合物として、下記一般式(5)で示される化合物又は下記一般式(6)で示される化合物を用い、前記一般式(2)で示される中間体と触媒を使用して反応させることが好ましい。
RD’ (5)
(式中、RD’は反応性官能基を持つ不飽和の重合性化合物である。)
RC’RD (6)
(式中、RDは前記と同様であり、RC’は、1価の反応性基である。)
(式中、X、RY、RZ、y、RZ’、及びRZ”は前記と同様であり、RY’は窒素原子、酸素原子、硫黄原子、及び炭素原子から選択されるいずれかの原子を0個又は1個含む3価の官能基、Tは水酸基、塩素原子、及び臭素原子から選択されるいずれかの原子である。)
GDBE [CH2=CH(CH2)2OCH2]2CHOHの合成
温度計、撹拌装置、窒素導入管の付いた滴下ロートを装着した3口フラスコに3−ブテン−1−オール(3.5mol)、水酸化カリウム(3.2mol)と臭化テトラブチルアンモニウム(0.2mol)を加え、室温にて撹拌後、滴下ロートにエピクロロヒドリン(1.0mol)を加え、内部温度が45℃を維持するように滴下した。滴下後、オイルバスを用いて60℃で加熱撹拌し、グリシジルエーテル由来の1H−NMRのシグナル(2〜3ppm)が消失したことを確認後、反応温度を室温に戻し、4M塩酸により中和し、水での洗浄、飽和食塩水処理、芒硝処理、ろ過処理した後、原料のアルコールを減圧下で留去し、残渣を蒸留(130℃/600Pa)することで生成物を得た。分光学的データは
1H−NMR(400MHz,CDCl3) δ 2.34(tq, J=1.2, 6.7Hz, 4H), 3.48(dd, J=9.8, 6.3Hz, 4H), 3.53(dd, J=6.8, 1.6Hz, 4H), 3.94(ddd, J=11.6, 6.2, 3.8Hz, 1H), 5.04(dq, J=9.1, 1.6Hz, 2H), 5.09(dq, J=17.2, 1.7Hz, 2H), 5.81(ddd, J=17.2, 9.1, 6.7Hz, 2H).
13C−NMR (100MHz,CDCl3) δ 34.14(CH2×2), 69.50(CH), 70.82(CH2×2), 71.94(CH2×2), 116.56(CH2=CH×2), 135.16(CH2=CH×2).
IR (NaCl) ν 914, 995, 1023, 1112, 1382, 2864, 3077, 3442.
となり、[CH2=CH(CH2)2OCH2]2CHOHを収率は82%で合成できた。
GDME [CH2=C(CH3)CH2OCH2]2CHOHの合成
[合成例1]の3−ブテン−1−オールをβ―メタリルアルコールに変えた以外は同様の方法で合成した。なお、蒸留(130℃/600Pa)の条件は[合成例1]と同じで生成物を得た。分光学的データは
1H−NMR(400MHz,CDCl3) δ 2.34(tq, J=1.2, 6.7Hz, 4H), 3.48(dd, J=9.8, 6.3Hz, 4H), 3.53(dd, J=6.8, 1.6Hz, 4H), 3.94(ddd, J=11.6, 6.2, 3.8Hz, 1H), 5.04(dq, J=9.1, 1.6Hz, 2H), 5.09(dq, J=17.2, 1.7Hz, 2H), 5.81(ddd, J=17.2, 9.1, 6.7Hz, 2H).
13C−NMR (100MHz,CDCl3) δ 34.14(CH2×2), 69.50(CH), 70.82(CH2×2), 71.94(CH2×2), 116.56(CH2=CH×2), 135.16(CH2=CH×2).
IR (NaCl) ν 914, 995, 1023, 1112, 1382, 2864, 3077, 3442.
となり、[CH2=C(CH3)CH2OCH2]2CHOHを収率は80%で合成できた。
GDiPE [CH2=C(CH3)(CH2)2OCH2]2CHOHの合成
[合成例1]の3−ブテン−1−オールを3−メチルー3−ブテン−1−オールに変えた以外は合成例1と同様の方法で合成した。なお、蒸留(135℃/250Pa)ので生成物を得た。分光学的データは
1H−NMR(400MHz,CDCl3) δ 2.34(tq, J=1.2, 6.7Hz, 4H), 3.48(dd, J=9.8, 6.3Hz, 4H), 3.53(dd, J=6.8, 1.6Hz, 4H), 3.94(ddd, J=11.6, 6.2, 3.8Hz, 1H), 5.04(dq, J=9.1, 1.6Hz, 2H), 5.09(dq, J=17.2, 1.7Hz, 2H), 5.81(ddd, J=17.2, 9.1, 6.7Hz, 2H).
13C−NMR (100MHz,CDCl3) δ 34.14(CH2×2), 69.50(CH), 70.82(CH2×2), 71.94(CH2×2), 116.56(CH2=CH×2), 135.16(CH2=CH×2).
IR (NaCl) ν 914, 995, 1023, 1112, 1382, 2864, 3077, 3442.
となり、[CH2=C(CH3)(CH2)2OCH2]2CHOHを収率は76%で合成できた。
[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOHの合成
温度計、マグネチックスターラーバー、窒素導入管を装着した100mL三つ口フラスコに1−ブチル−9−ヒドロ−1,1,3,3,5,5,7,7,9,9−デカメチルペンタシロキサン(H−シロキサン) 20.6g(49.9mmol)とトルエン 11.1g(30wt%)とBHT 3.7mg(100ppm)をフラスコに入れ、合成例1のGDBE 5.00g(25.0mmol)を入れた滴下ロートをフラスコに装着し、内部温度を70℃まで撹拌しながら昇温した。そこに、カーステッド触媒(Karstedt,Pt2[[(CH2=CH)(CH3)2Si]2O]3)の0.5wt%トルエン溶液をマイクロシリンジにて21.9mg(3ppm)加えそのままの温度で10分間撹拌した後、内部温度が75℃を超えないようにGDBEを継続的に滴下し、発熱が収まった後、1H−NMRを測定し、末端オレフィンのシグナルが消失していることを確認した。その後、反応温度を室温まで戻した後、残留H−シロキサンとトルエンを減圧下で留去し(130℃/<1KPa)、無色透明油状の生成物を得た。得られた生成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR(400MHz,CDCl3) δ 0.04(s, 36H), 0.06(s, 24H), 0.49−0.59(m, 8H),0.88(t, J=6.9Hz, 6H), 3.49−3.52(m, 8H), 3.90−3.97(m, 1H).
13C−NMR (75MHz,CDCl3) δ 0.09(CH3×8), 0.77(CH3×4), 0.87(CH3×8), 13.51(CH2×2), 17.73(CH2×2), 17.82(CH2×2), 19.60(CH2×2), 25.24(CH2×2), 26.08(CH2×2), 32.98(CH2×2), 69.22(CH), 71.01(CH2×2), 71.89(CH2×2).
IR (NaCl) ν 796, 1031, 1259, 2873, 2925, 3473.
となり、[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOHを収率94%で得た。
[[(CH3)3SiO]2Si(CH3)(CH2)4OCH2]2CHOHの合成
合成例4の1−ブチル−9−ヒドロ−1,1,3,3,5,5,7,7,9,9−デカメチルペンタシロキサンを3−ヒドロ−1,1,1,3,5,5,5−ヘプタメチルトリシロキサンに変えた以外は合成例4と同様のモル比及び作業手順で、無色透明油状の生成物を得た。得られた成物の分光学的データは
1H−NMR (400MHz、CDCl3) δ 0.00(s, 6H), 0.05−0.12(m, 36H), 0.46(t, J=8.4Hz, 4H), 1.31−1.43(m, 4H), 1.60(quin., J=6.9Hz, 4H), 3.41−3.52(m, 8H), 3.89−3.97(m, 1H).
13C−NMR (75MHz,CDCl3) δ −0.51(CH3×2), 1.62(CH3×4), 17.18(CH2×2), 19.49(CH2×2), 32.80(CH2×2), 69.26(CH), 71.04(CH2×2), 71.92(CH2×2).
IR (NaCl) ν 756, 795, 1032, 1172, 1256, 2957, 3443.
となり、[[(CH3)3SiO]2Si(CH3)(CH2)4OCH2]2CHOHを収率85%で得た。
[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)CH2OCH2]2CHOHの合成
合成例4のGDBEを合成例2で得たGDMEに変えた以外は合成例4と同様のモル比及び作業手順で、無色透明油状の生成物を得た。得られた成物の分光学的データは
1H−NMR (400MHz、CDCl3) δ 0.00(s, 6H), 0.05−0.12(m, 36H), 0.46(t, J=8.4Hz, 4H), 1.31−1.43(m, 4H), 1.60(quin., J=6.9Hz, 4H), 3.41−3.52(m, 8H), 3.89−3.97(m, 1H).
13C−NMR (75MHz,CDCl3) δ −0.51(CH3×2), 1.62(CH3×4), 17.18(CH2×2), 19.49(CH2×2), 32.80(CH2×2), 69.26(CH), 71.04(CH2×2), 71.92(CH2×2).
IR (NaCl) ν 756, 795, 1032, 1172, 1256, 2957, 3443.
となり、[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)CH2OCH2]2CHOHを収率90%で得た。
[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)(CH2)2OCH2]2CHOHの合成
合成例4のGDBEを合成例3で得たGDiPEに変えた以外は合成例4と同様のモル比及び作業手順で、無色透明油状の生成物を得た。得られた成物の分光学的データは
1H−NMR (400MHz、CDCl3) δ 0.00(s, 6H), 0.05−0.12(m, 36H), 0.46(t, J=8.4Hz, 4H), 1.31−1.43(m, 4H), 1.60(quin., J=6.9Hz, 4H), 3.41−3.52(m, 8H), 3.89−3.97(m, 1H).
13C−NMR (75MHz,CDCl3) δ −0.51(CH3×2), 1.62(CH3×4), 17.18(CH2×2), 19.49(CH2×2), 32.80(CH2×2), 69.26(CH), 71.04(CH2×2), 71.92(CH2×2).
IR (NaCl) ν 756, 795, 1032, 1172, 1256, 2957, 3443.
となり、[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)(CH2)2OCH2]2CHOHを収率90%で得た。
[[(CH3)3SiO]2Si(CH3)CH2CH(CH3)(CH2)2OCH2]2CHOHの合成
合成例5のGDBEを合成例3で得たGDiPEに変えた以外は合成例5と同様のモル比及び作業手順で、無色透明油状の生成物を得た。得られた成物の分光学的データは
1H−NMR (400MHz、CDCl3) δ 0.00(s, 6H), 0.05−0.12(m, 36H), 0.46(t, J=8.4Hz, 4H), 1.31−1.43(m, 4H), 1.60(quin., J=6.9Hz, 4H), 3.41−3.52(m, 8H), 3.89−3.97(m, 1H).
13C−NMR (75MHz,CDCl3) δ −0.51(CH3×2), 1.62(CH3×4), 17.18(CH2×2), 19.49(CH2×2), 32.80(CH2×2), 69.26(CH), 71.04(CH2×2), 71.92(CH2×2).
IR (NaCl) ν 756, 795, 1032, 1172, 1256, 2957, 3443.
となり、[[(CH3)3SiO]2Si(CH3)CH2CH(CH3)(CH2)2OCH2]2CHOHを収率86%で得た。
[Bu[Si(CH3)2O]4Si(CH3)2(CH2)3OCH2]2CHOHの合成
合成例4のGDBEをGDAE([CH2=CHCH2OCH2]2CHOH)に変えた以外は合成例4と同様のモル比及び作業手順で、無色透明油状生成物を得た。得られた生成物の分光学的データは分子量分布 Mw/Mn = 1.01で
1H−NMR (400MHz、CDCl3) δ 0.00−0.14(m, 60H), 0.44−0.69(m, 8H), 0.88(t, J=6.6Hz, 6H), 1.23−1.39(m, 8H), 1.45−1.66(m, 8H), 3.37−3.78(m, 9H).
13C−NMR (75MHz,CDCl3) δ 0.04(CH3×8), 0.72(CH3×4), 0.82(CH3×8), 13.39(CH2×2), 17.70(CH2×2), 17.77(CH2×2), 19.53(CH2×2), 25.19(CH2×2), 33.00(CH2×2), 69.15(CH), 70.99(CH2×2), 71.88(CH2×2).
IR (NaCl) ν 797, 841, 1032,1161, 1259, 2875, 2930, 3433.
となり、[Bu[Si(CH3)2O]4Si(CH3)2(CH2)3OCH2]2CHOHを収率93%で得た。
[(CH3)3SiO]2Si(CH3)(CH2)3OCH2]2CHOHの合成
合成例9の1−ブチル−9−ヒドロ−1,1,3,3,5,5,7,7,9,9−デカメチルペンタシロキサンを3−ヒドロ−1,1,1,3,5,5,5−ヘプタメチルトリシロキサンに変えた以外は合成例9と同様のモル比及び作業手順で、無色透明油状の生成物を得た。得られた成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR (400MHz、CDCl3) δ 0.01(s, 6H), 0.09(s, 36H), 0.45(t, J=8.4Hz, 4H), 1.60(quin., J=7.8Hz, 4H), 2.47(dd, J=4.0, 1.2Hz, 1H), 3.37−3.53(m, 8H), 3.95(q, J=5.4Hz, 1H).
13C−NMR (75MHz, CDCl3) δ −0.63(CH3×2), 1.50(CH3×12), 13.31(CH2×2), 17.89(CH3), 63.40(CH), 69.23(CH2×2), 71.09(CH2).
IR (NaCl) ν 755, 782, 769, 841, 1049, 1258, 2957, 3454.
となり、[(CH3)3SiO]2Si(CH3)(CH2)3OCH2]2CHOHを収率89%で得た。
[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2の合成
温度計、滴下ロート、窒素導入管を装着し、マグネティックスターラーバーを入れた100mL3口フラスコに合成例4で得られた上記[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOH 20.5g(20.0mol)に、(株)同仁化学研究所製の鉄アセチルアセテート[Fe(acac)3]触媒 0.35mg(50μmol%)、BHT 2.40mg(100ppm)を加え、撹拌しながら40℃まで加熱した。そこに滴下ロートからカレンズMOI 3.26g(21.0mol)を内温が45℃を超えないように滴下した。そのままの温度で30分間撹拌後、1H−NMRによりカルバミン酸エステル由来のシグナル(5.00ppm)が水素比で1H分生成したら反応温度を室温へ戻し、活性炭71mg(0.3wt%)を加え、1時間室温にて撹拌した。その後、活性炭をろ別し、減圧下で小過剰のカレンズMOIを留去し(90〜100℃/<1KPa)、淡黄色透明油状の生成物を得た。得られた生成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR (400MHz,CDCl3) δ 0.06−0.10(m, 60H), 0.49−0.58(m, 8H), 0.88(t, J=6.9Hz, 6H), 1.24−1.43(m, 12H), 1.59(quin., J=1.0Hz, 3H), 3.47−3.62(m, 10H),4.22(t, J=5.2Hz, 20H), 6.11(dd, J=1.3, 0.8Hz, 1H), 5.59(quin., J=1.5Hz, 1H), 4.95−5.07(m, 2H), 5.59(quin., J=1.5Hz, 1H), 6.11(dd, J=1.3, 0.8Hz, 1H).
13C−NMR (75MHz,CDCl3) δ 0.06(CH3×8), 0.63(CH3×4), 0.80(CH3×8), 13.37(CH2×2), 17.82(CH2×2), 17.83(CH2×2), 19.55(CH2×2), 25.30(CH2×2), 25.99(CH2×2), 33.02(CH2×2), 40.65(CH2) ,63.21(CH2), 68.77(CH), 71.11(CH2×2), 71.84(CH2×2), 125.25(CH2=C(CH3)), 136.01(CH2=C(CH3)), 155.69(C=O), 166.66(C=O).
IR (NaCl) ν 798, 840, 1033, 1160, 1259, 1725, 2926, 2959, 3356.
となり、[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2を収率78%で得た。
[[(CH3)3SiO]2Si(CH3)(CH2)4OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2の合成
実施例1中の[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOHを、合成例5で得た[[(CH3)3SiO]2Si(CH3)(CH2)4OCH2]2CHOHに変えた以外は実施例1と同様のモル比及び作業手順で、淡黄色透明油状の生成物を得た。得られた成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR (400MHz、CDCl3) δ −0.01(s, 6H), 0.04−0.13(m, 36H), 0.37−0.50(m, 4H), 1.46−1.66(m, 4H), 1.94(t, J=1.3Hz, 3H), 3.33−3.54(m, 6H), 3.54−3.65(m, 4H), 4.22(t, J=5.2Hz, 2H), 4.96−5.07(m, 2H), 5.59(t, J=1.6Hz, 1H), 6.11(s, 1H).
13C−NMR (75MHz,CDCl3) δ −0.66(CH3×2), 1.52(CH3×12), 13.29(CH2×2), 17.91(CH3), 23.0(CH2×2), 39.91(CH2), 63.36(CH2), 69.11(CH2×2), 71.75(CH2), 73.73(CH2×2), 125.30(CH2=C(CH3)), 135.88(CH2=C), 155.73(C=O), 166.62(C=O).
IR (NaCl) ν 755, 797, 1049, 1162, 1258,1725, 2958, 3356.
となり、[[(CH3)3SiO]2Si(CH3)(CH2)4OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2を収率73%で得た。
[Bu[Si(CH 3 ) 2 O] 4 Si(CH 3 ) 2 (CH2)4OCH2]2CHOC(=O)NH[(CH2)2O]2C(=O)C(CH3)=CH2の合成
合成例4で得たジシロキサン[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOHを用いて、カレンズMOIをカレンズMOI−EGに変えた以外は実施例1と同様のモル比及び作業手順で、淡黄色透明油状の生成物を得た。得られた生成物の分光学的データは
1H−NMR(400MHz、CDCl3) δ 0.00−0.18(m, 60H), 0.45−0.58(m, 8H), 0.88(t, J=6.9Hz, 6H), 1.23−1.38(m, 8H), 1.48−1.63(m, 8H), 1.95(s, 3H), 3.30−3.48(m, 4H), 3.50−3.64(m, 8H),3.69(t, J=4.6Hz, 2H), 4.28(t, J=4.6Hz, 2H), 4.93−5.02(m, 1H), 5.07−5.18(m, 1H), 5.58(s, 1H), 6.13(s, 1H).
13C−NMR (75MHz,CDCl3) δ −0.14(CH3×4), −0.08(CH3×4), 0.78(CH3×4), 0.87(CH3×8), 13.49(CH2×2), 13.96(CH2×2), 17.97(CH3), 23.22(CH2×2), 25.23(CH2×2), 26.06(CH2×2), 40.66(CH2), 63.35(CH2), 68.75(CH), 69.82(CH2), 71.92(CH2), 73.93(CH2×2), 125.22(CH2=C(CH3)), 135.99(CH2=C(CH3)), 155.74(C=O), 166.70(C=O).
IR (NaCl) ν 779, 839, 1034, 1167, 1259, 1725, 2927, 2959, 3356.
となり、[Bu[Si(CH 3 ) 2 O] 4 Si(CH 3 ) 2 (CH2)4OCH2]2CHOC(=O)NH[(CH2)2O]2C(=O)C(CH3)=CH2を収率83%で得た。
[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)CH2OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2の合成
実施例1中の[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOHを、合成例6で得た[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)CH2OCH2]2CHOHに変えた以外は実施例1と同様のモル比及び作業手順で、淡黄色透明油状の生成物を得た。得られた成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR (400MHz、CDCl3) δ −0.01(s, 6H), 0.04−0.13(m, 36H), 0.37−0.50(m, 4H), 1.46−1.66(m, 4H), 1.94(t, J=1.3Hz, 3H), 3.33−3.54(m, 6H), 3.54−3.65(m, 4H), 4.22(t, J=5.2Hz, 2H), 4.96−5.07(m, 2H), 5.59(t, J=1.6Hz, 1H), 6.11(s, 1H).
13C−NMR (75MHz,CDCl3) δ −0.66(CH3×2), 1.52(CH3×12), 13.29(CH2×2), 17.91(CH3), 23.0(CH2×2), 39.91(CH2), 63.36(CH2), 69.11(CH2×2), 71.75(CH2), 73.73(CH2×2), 125.30(CH2=C(CH3)), 135.88(CH2=C), 155.73(C=O), 166.62(C=O).
IR (NaCl) ν 755, 797, 1049, 1162, 1258,1725, 2958, 3356.
となり、[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)CH2OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2を収率72%で得た。
[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)(CH2)2OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2の合成
実施例1中の[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOHを、合成例7で得た[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)(CH2)2OCH2]2CHOHに変えた以外は実施例1と同様のモル比及び作業手順で、淡黄色透明油状の生成物を得た。得られた成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR (400MHz、CDCl3) δ −0.01(s, 6H), 0.04−0.13(m, 36H), 0.37−0.50(m, 4H), 1.46−1.66(m, 4H), 1.94(t, J=1.3Hz, 3H), 3.33−3.54(m, 6H), 3.54−3.65(m, 4H), 4.22(t, J=5.2Hz, 2H), 4.96−5.07(m, 2H), 5.59(t, J=1.6Hz, 1H), 6.11(s, 1H).
13C−NMR (75MHz,CDCl3) δ −0.66(CH3×2), 1.52(CH3×12), 13.29(CH2×2), 17.91(CH3), 23.0(CH2×2), 39.91(CH2), 63.36(CH2), 69.11(CH2×2), 71.75(CH2), 73.73(CH2×2), 125.30(CH2=C(CH3)), 135.88(CH2=C), 155.73(C=O), 166.62(C=O).
IR (NaCl) ν 755, 797, 1049, 1162, 1258,1725, 2958, 3356.
となり、[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)(CH2)2OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2を収率72%で得た。
[[(CH3)3SiO]2Si(CH3)CH2CH(CH3)(CH2)2OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2の合成
実施例1中の[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOHを、合成例8で得た[[(CH3)3SiO]2Si(CH3)CH2CH(CH3)(CH2)2OCH2]2CHOHに変えた以外は実施例1と同様のモル比及び作業手順で、淡黄色透明油状の生成物を得た。得られた成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR (400MHz、CDCl3) δ −0.01(s, 6H), 0.04−0.13(m, 36H), 0.37−0.50(m, 4H), 1.46−1.66(m, 4H), 1.94(t, J=1.3Hz, 3H), 3.33−3.54(m, 6H), 3.54−3.65(m, 4H), 4.22(t, J=5.2Hz, 2H), 4.96−5.07(m, 2H), 5.59(t, J=1.6Hz, 1H), 6.11(s, 1H).
13C−NMR (75MHz,CDCl3) δ −0.66(CH3×2), 1.52(CH3×12), 13.29(CH2×2), 17.91(CH3), 23.0(CH2×2), 39.91(CH2), 63.36(CH2), 69.11(CH2×2), 71.75(CH2), 73.73(CH2×2), 125.30(CH2=C(CH3)), 135.88(CH2=C), 155.73(C=O), 166.62(C=O).
IR (NaCl) ν 755, 797, 1049, 1162, 1258,1725, 2958, 3356.
となり、[[(CH3)3SiO]2Si(CH3)CH2CH(CH3)(CH2)2OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2を収率75%で得た。
[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)(CH2)2OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2の合成
実施例1中の[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOHを、合成例7で得た[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)(CH2)2OCH2]2CHOHを用いて、カレンズMOIをカレンズMOI−EGに変えた以外は実施例1と同様のモル比及び作業手順で、淡黄色透明油状の生成物を得た。得られた成物の分光学的データは
得られた成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR (400MHz、CDCl3) δ −0.01(s, 6H), 0.04−0.13(m, 36H), 0.37−0.50(m, 4H), 1.46−1.66(m, 4H), 1.94(t, J=1.3Hz, 3H), 3.33−3.54(m, 6H), 3.54−3.65(m, 4H), 4.22(t, J=5.2Hz, 2H), 4.96−5.07(m, 2H), 5.59(t, J=1.6Hz, 1H), 6.11(s, 1H).
13C−NMR (75MHz,CDCl3) δ −0.66(CH3×2), 1.52(CH3×12), 13.29(CH2×2), 17.91(CH3), 23.0(CH2×2), 39.91(CH2), 63.36(CH2), 69.11(CH2×2), 71.75(CH2), 73.73(CH2×2), 125.30(CH2=C(CH3)), 135.88(CH2=C), 155.73(C=O), 166.62(C=O).
IR (NaCl) ν 755, 797, 1049, 1162, 1258,1725, 2958, 3356.
となり、[[Bu[Si(CH3)2O]4Si(CH3)2]CH2CH(CH3)(CH2)2OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2を収率76%で得た。
[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)3OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2の合成
実施例1の[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)4OCH2]2CHOHを合成例9で得た [[Bu[Si(CH3)2O]4Si(CH3)2(CH2)3OCH2]2CHOHに変えた以外は実施例1と同様のモル比及び作業手順で、淡黄色透明油状の生成物を得た。得られた生成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR (400MHz、CDCl3) δ 0.00−0.12(m,60H), 0.46−0.56(m, 8H), 0.88(t,J=6.9Hz,6H), 1.25−1.35(m, 8H), 1.50−1.65(m, 8H), 1.94(s, 3H), 3.42−3.65(m, 10H), 4.22(t, J=4.7Hz, 2H), 4.88−5.06(m, 2H), 5.59(t, J=1.5Hz, 1H), 6.11(s,1H).
13C−NMR (75MHz,CDCl3) δ 0.08(CH3×8), 0.65(CH3×4), 0.83(CH3×8), 13.67(CH2×2), 17.84(CH2×2), 17.85(CH2×2), 19.56(CH2×2), 25.32(CH2×2), 33.04(CH2×2), 40.67(CH2), 63.23(CH2), 68.79(CH), 71.13(CH2×2), 71.86(CH2×2), 125.28(CH2=C(CH3)), 135.99(CH2=C(CH3)), 155.70(C=O),166.68(C=O).
IR (NaCl) ν 798, 839, 1033, 1162, 1259, 1725, 2873, 2926, 2959, 3356.
となり、[[Bu[Si(CH3)2O]4Si(CH3)2(CH2)3OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2を収率67%で得た。
[[(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH2)3OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2の合成
実施例8の[Bu[Si(CH3)2O]4Si(CH3)2(CH2)3OCH2]2CHOHを合成例10で得た[[(CH3)3SiO]2Si(CH3)(CH2)3OCH2]2CHOHに変えた以外は実施例2と同様のモル比及び作業手順で、淡黄色透明油状の生成物を得た。得られた生成物の分光学的データは分子量分布Mw/Mn=1.01で
1H−NMR (400MHz、CDCl3) δ 0.00(s, 6H), 0.03−0.15(m, 36H), 0.38−0.49(m, 4H), 1.95(t. J=1.2Hz, 3H), 3.32−3.55(m,6H), 3.56−3.67(m,4H), 4.23(t, J=5.6Hz, 2H), 4.93−5.08(m, 2H), 5.60(t, J=1.2Hz, 1H), 6.11(s, 1H).
13C−NMR (75MHz, CDCl3) δ −0.63(CH3×2), 1.50(CH3×12), 13.31(CH2×2), 17.89(CH3), 39.93(CH2), 63.40(CH2), 69.15(CH2×2), 71.79(CH2), 73.75(CH2×2), 125.25(CH2=C(CH3)), 135.86(CH2=C), 155.70(C=O), 166.60(C=O).
IR (NaCl) ν 756, 798, 1051, 1160, 1256, 1726, 2927, 2960, 3355.
となり、[[(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH2)3OCH2]2CHOC(=O)NH(CH2)2OC(=O)C(CH3)=CH2を収率99%で得た。
Claims (9)
- 下記一般式(1)で示される化合物であることを特徴とする対称ハイパーブランチ型シリコーン変性重合性化合物。
(RARB)2CHORC cRD (1)
(式中、RAはBu[Si(CH3)2O]4Si(CH3)2−又は[(CH3)3SiO]2Si(CH3)−であり、Buはブチル基を表す。RBは−CH2CRb1Rb2(CRb3Rb4)n1OCH2−(但し、式(1)において(RACH2CRb1Rb2(CRb3Rb4)n1OCH2)2CHORC cRDのように配置される)で示され、Rb1、Rb2、Rb3、及びRb4がそれぞれ同一でも異なっていても良い水素原子又は互いに結合しても良い炭素数1〜10の直鎖、分岐又は環状の炭化水素基である2価のハイドロカルボニレンメチレンエーテル基、n1は0〜10から選択される整数である。但し、n1が1のとき、Rb1が炭素数1〜10の炭化水素基、Rb2が水素原子を示す。
RCは、−XRY yRZO−、−XRY yCRZ’RZ”O−で示される2価の連結基、及び、炭素数2〜10で繰り返し単位が整数1〜10のオリゴアルキレンオキシ基から選択されるいずれかの連結基(式中、Xは−CH2−、−C(=O)−、及び−C(=S)−から選択されるいずれかであり、RYは−NH−であり、RZは酸素原子で置換してもよい炭素数2〜10の直鎖、分岐又は環状のアルキレン基で、yは0又は1から選択される整数であり、RZ’とRZ”はそれぞれ炭素数1〜10のアルキル基である。)であり、
cは0又は1である。
RDは、ヘテロ原子を含む炭素数1〜10の直鎖、分岐又は環状の置換基を含有しても良いアクリル基、メタクリル基、アルキニル基、スチリル基、インデニル基、アルケニル基、シクロアルケニル基、ノルボルネニル基、共役又は非共役アルカジエン基、及びビニルエーテル基のいずれかから選択される1価の不飽和の重合性官能基である。) - 前記一般式(1)中のRBで示される2価のハイドロカルボニレンメチレンエーテル基のうち、n1が1〜10から選択される整数であることを特徴とする請求項1に記載の対称ハイパーブランチ型シリコーン変性重合性化合物。
- 請求項1又は請求項2に記載の対称ハイパーブランチ型シリコーン変性重合性化合物の製造方法であって、
前記一般式(1)で示される化合物を、下記一般式(2)で示される中間体と不飽和の重合性官能基を有する化合物とを反応させることにより製造することを特徴とするモジュール化した製造方法。
(RARB)2CHOH (2)
(式中、RA、RBは前記と同様である。) - 前記一般式(2)で示される中間体を、下記一般式(3)で示される化合物と下記一般式(4)で示される化合物とをヒドロシリル化反応させることにより製造することを特徴とする請求項3に記載のモジュール化した製造方法。
RA’ (3)
(式中、RA’は1−ブチル−9−ヒドロ−1,1,3,3,5,5,7,7,9,9−デカメチルペンタシロキサン又は3−ヒドロ−1,1,1,3,5,5,5−ヘプタメチルトリシロキサンである。)
RB’ 2CHOH (4)
(式中、RB’はCH2=CRb1(CRb3Rb4)n1’OCH2−で示される末端に二重結合を持つ1価のハイドロカルボニレンメチレンエーテル基であり、Rb1、Rb3、及びRb4は前記と同様であり、n1’は0〜10から選択される整数である。但し、n1’が1のとき、Rb1が炭素数1〜10の炭化水素基を示す。) - 前記一般式(4)中のn1’が1〜10から選択される整数であることを特徴とする請求項4に記載のモジュール化した製造方法。
- 前記ヒドロシリル化反応に遷移金属触媒とラジカル捕捉剤を使用することを特徴とする請求項4又は請求項5に記載のモジュール化した製造方法。
- 前記遷移金属触媒が白金触媒であることを特徴とする請求項6に記載のモジュール化した製造方法。
- 前記不飽和の重合性官能基を有する化合物として、下記一般式(5)で示される化合物又は下記一般式(6)で示される化合物を用い、前記一般式(2)で示される中間体と触媒を使用して反応させることを特徴とする請求項3乃至請求項7のいずれか一項に記載のモジュール化した製造方法。
RD’ (5)
(式中、RD’は、ヘテロ原子を含む炭素数1〜10の直鎖、分岐又は環状の置換基を含有しても良いアクリル基、メタクリル基、アルキニル基、スチリル基、インデニル基、アルケニル基、シクロアルケニル基、ノルボルネニル基、共役又は非共役アルカジエン基、及びビニルエーテル基のいずれかから選択される不飽和基と、水酸基、アミノ基、ヒドロキシカルボニル基、アルデヒド基、酸ハロゲン基、エステル基、ハロギ酸エステル基、ハロゲン化アルキル基、イソシアネート基、イソチオシアネート基、ケテン基、リン酸基、エポキシ基、アジリジン基、トシル基、メシル基、トリフルオロメタンスルホニル基、ブロモ基、ヨード基、ハロゲン化アリール基、及びニトロアリール基のいずれかから選択される反応性官能基とを直接結合して、又は、連結基を介して分子中に含む不飽和の重合性化合物である。)
RC’RD (6)
(式中、RDは前記と同様であり、
RC’は、X=RY’RZO−、T−X−RY yRZO−、X=RY’CRZ’RZ”O−、T−X−RY yCRZ’RZ”O−で示される1価の反応性基、及び、片末端に反応性基を持ち炭素数2〜10で繰り返し単位が整数1〜10のオリゴアルキレンオキシ基から選択されるいずれかの反応性基(式中、X、RY、RZ、y、RZ’、及びRZ”は前記と同様であり、RY’は窒素原子、Tは水酸基、塩素原子、及び臭素原子から選択されるいずれかの原子である。)である。) - 請求項8に記載のモジュール化した製造方法であって、前記一般式(2)で示される中間体と前記不飽和の重合性官能基を有する化合物とを反応させる際に使用する触媒として、1種類以上の有機又は無機のスズ錯体、チタン錯体、鉄錯体、銅錯体、亜鉛錯体、アルミニウム錯体、ジルコニウム錯体、イットリウム錯体、スカンジウム錯体、インジウム錯体、ランタニウム錯体、セリウム錯体、サマリウム錯体、ユウロピウム錯体、及びケイ素錯体のいずれかから選ばれるルイス酸又は第3級有機塩基を用い、該触媒を前記一般式(2)で示される中間体に対して0.001〜0.500mol%使用することを特徴とするモジュール化した製造方法。
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TWI794742B (zh) | 2020-02-18 | 2023-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
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