JP4524554B2 - γ,δ−不飽和カルボン酸及びそのシリルエステルの製造方法、カルボキシル基を有する有機ケイ素化合物及びその製造方法 - Google Patents
γ,δ−不飽和カルボン酸及びそのシリルエステルの製造方法、カルボキシル基を有する有機ケイ素化合物及びその製造方法 Download PDFInfo
- Publication number
- JP4524554B2 JP4524554B2 JP2003333014A JP2003333014A JP4524554B2 JP 4524554 B2 JP4524554 B2 JP 4524554B2 JP 2003333014 A JP2003333014 A JP 2003333014A JP 2003333014 A JP2003333014 A JP 2003333014A JP 4524554 B2 JP4524554 B2 JP 4524554B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- atom
- silicon
- atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 silyl ester Chemical class 0.000 title claims description 130
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title claims description 49
- 238000004519 manufacturing process Methods 0.000 title claims description 33
- 150000003961 organosilicon compounds Chemical class 0.000 title claims description 25
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 205
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 114
- 125000005843 halogen group Chemical group 0.000 claims description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 229910052710 silicon Inorganic materials 0.000 claims description 57
- 150000002430 hydrocarbons Chemical group 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000004104 aryloxy group Chemical group 0.000 claims description 29
- 125000005386 organosiloxy group Chemical group 0.000 claims description 25
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 claims description 16
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 239000001257 hydrogen Chemical group 0.000 claims description 3
- 229910052739 hydrogen Chemical group 0.000 claims description 3
- 238000006884 silylation reaction Methods 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003610 charcoal Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 35
- 150000001875 compounds Chemical class 0.000 description 29
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 24
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 22
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000006459 hydrosilylation reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 229910052697 platinum Inorganic materials 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 7
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 238000005828 desilylation reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 6
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- ZQCDDIKURMLFQX-UHFFFAOYSA-N triethylsilyl 2,2-dimethylpent-4-enoate Chemical compound CC[Si](CC)(CC)OC(=O)C(C)(C)CC=C ZQCDDIKURMLFQX-UHFFFAOYSA-N 0.000 description 5
- BGUAPYRHJPWVEM-UHFFFAOYSA-N 2,2-dimethyl-4-pentenoic acid Chemical compound OC(=O)C(C)(C)CC=C BGUAPYRHJPWVEM-UHFFFAOYSA-N 0.000 description 4
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006136 alcoholysis reaction Methods 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 3
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DWECCSLIPBMGKH-UHFFFAOYSA-N [ethoxy(dimethyl)silyl] 2,2-dimethylpent-4-enoate Chemical compound CCO[Si](C)(C)OC(=O)C(C)(C)CC=C DWECCSLIPBMGKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 3
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 3
- 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 3
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 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 3
- 239000005457 ice water Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000005920 sec-butoxy group Chemical group 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000004079 stearyl 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])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])[H] 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- BWFOZZTYGDHIJN-UHFFFAOYSA-N 3-chloropropyl-dimethylsilyloxy-dimethylsilane Chemical compound C[SiH](C)O[Si](C)(C)CCCCl BWFOZZTYGDHIJN-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- YTEISYFNYGDBRV-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)C YTEISYFNYGDBRV-UHFFFAOYSA-N 0.000 description 2
- ZLVOATIRJZQYKU-UHFFFAOYSA-N [chloro(dimethyl)silyl] 2,2-dimethylpent-4-enoate Chemical compound C=CCC(C)(C)C(=O)O[Si](C)(C)Cl ZLVOATIRJZQYKU-UHFFFAOYSA-N 0.000 description 2
- GDDVTIGTERZVBW-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)(C)C GDDVTIGTERZVBW-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- UAQXBMQRCCALNJ-UHFFFAOYSA-N butan-2-yloxy(dimethyl)silane Chemical compound CCC(C)O[SiH](C)C UAQXBMQRCCALNJ-UHFFFAOYSA-N 0.000 description 2
- YCITZMJNBYYMJO-UHFFFAOYSA-N chloro(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](Cl)C1=CC=CC=C1 YCITZMJNBYYMJO-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- PFMKUUJQLUQKHT-UHFFFAOYSA-N dichloro(ethyl)silicon Chemical compound CC[Si](Cl)Cl PFMKUUJQLUQKHT-UHFFFAOYSA-N 0.000 description 2
- VIRVTHOOZABTPR-UHFFFAOYSA-N dichloro(phenyl)silane Chemical compound Cl[SiH](Cl)C1=CC=CC=C1 VIRVTHOOZABTPR-UHFFFAOYSA-N 0.000 description 2
- UWGIJJRGSGDBFJ-UHFFFAOYSA-N dichloromethylsilane Chemical compound [SiH3]C(Cl)Cl UWGIJJRGSGDBFJ-UHFFFAOYSA-N 0.000 description 2
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 description 2
- SGKDAFJDYSMACD-UHFFFAOYSA-N dimethoxy(propyl)silane Chemical compound CCC[SiH](OC)OC SGKDAFJDYSMACD-UHFFFAOYSA-N 0.000 description 2
- RHBCYWAHUOTOJC-UHFFFAOYSA-N dimethyl(phenoxy)silicon Chemical compound C[Si](C)OC1=CC=CC=C1 RHBCYWAHUOTOJC-UHFFFAOYSA-N 0.000 description 2
- WTZAYPRBGBDDQT-UHFFFAOYSA-N dimethyl(phenylmethoxy)silane Chemical compound C[SiH](C)OCC1=CC=CC=C1 WTZAYPRBGBDDQT-UHFFFAOYSA-N 0.000 description 2
- OARYFQYHTWCNQO-UHFFFAOYSA-N dimethyl(propan-2-yloxy)silane Chemical compound CC(C)O[SiH](C)C OARYFQYHTWCNQO-UHFFFAOYSA-N 0.000 description 2
- XUKFPAQLGOOCNJ-UHFFFAOYSA-N dimethyl(trimethylsilyloxy)silicon Chemical compound C[Si](C)O[Si](C)(C)C XUKFPAQLGOOCNJ-UHFFFAOYSA-N 0.000 description 2
- BFFJBAVNIXLGLQ-UHFFFAOYSA-N dimethyl-[(2-methylpropan-2-yl)oxy]silane Chemical compound C[SiH](C)OC(C)(C)C BFFJBAVNIXLGLQ-UHFFFAOYSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- YSLVSGVAVRTLAV-UHFFFAOYSA-N ethyl(dimethoxy)silane Chemical compound CC[SiH](OC)OC YSLVSGVAVRTLAV-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VJOOEHFQQLYDJI-UHFFFAOYSA-N methoxy(dimethyl)silane Chemical compound CO[SiH](C)C VJOOEHFQQLYDJI-UHFFFAOYSA-N 0.000 description 2
- RMZSTOAGUSEJFY-UHFFFAOYSA-N methyl-[methyl(phenyl)silyl]oxy-phenylsilane Chemical compound C=1C=CC=CC=1[SiH](C)O[SiH](C)C1=CC=CC=C1 RMZSTOAGUSEJFY-UHFFFAOYSA-N 0.000 description 2
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 description 2
- 125000005295 norbornyloxy group Chemical group C12(CCC(CC1)C2)O* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000004344 phenylpropyl group Chemical group 0.000 description 2
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- XAASNKQYFKTYTR-UHFFFAOYSA-N tris(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)O[Si](C)(C)C XAASNKQYFKTYTR-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- HWEVQHXMPMFZNH-UHFFFAOYSA-N (4-chlorophenoxy)-dimethylsilane Chemical compound C[SiH](C)OC1=CC=C(Cl)C=C1 HWEVQHXMPMFZNH-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- JKQLUVWUXHZWGR-UHFFFAOYSA-N 2,2-dimethyl-5-triethoxysilylpentanoic acid Chemical compound CCO[Si](OCC)(OCC)CCCC(C)(C)C(O)=O JKQLUVWUXHZWGR-UHFFFAOYSA-N 0.000 description 1
- PIGJZPZYWKFDBR-UHFFFAOYSA-N 2,5-dimethyl-1-(4-methylpyridin-2-yl)pyrrole-3-carbaldehyde Chemical compound CC1=CC(C=O)=C(C)N1C1=CC(C)=CC=N1 PIGJZPZYWKFDBR-UHFFFAOYSA-N 0.000 description 1
- KPZZQMPORKJLMG-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethoxy-dimethylsilane Chemical compound COCCOCCO[SiH](C)C KPZZQMPORKJLMG-UHFFFAOYSA-N 0.000 description 1
- KVMAQXBSRFDBSI-UHFFFAOYSA-N 2-methoxyethoxy(dimethyl)silane Chemical compound COCCO[SiH](C)C KVMAQXBSRFDBSI-UHFFFAOYSA-N 0.000 description 1
- LTVRSJBNXLZFGT-UHFFFAOYSA-N 2-silylethenone Chemical compound [SiH3]C=C=O LTVRSJBNXLZFGT-UHFFFAOYSA-N 0.000 description 1
- UDIMUNKNMFGPJH-UHFFFAOYSA-N 3-chloropropyl(dimethyl)silicon Chemical compound C[Si](C)CCCCl UDIMUNKNMFGPJH-UHFFFAOYSA-N 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- KIGUHEZAHWXIMU-UHFFFAOYSA-N 5-[[(4-carboxy-4-methylpentyl)-dimethylsilyl]oxy-dimethylsilyl]-2,2-dimethylpentanoic acid Chemical compound OC(=O)C(C)(C)CCC[Si](C)(C)O[Si](C)(C)CCCC(C)(C)C(O)=O KIGUHEZAHWXIMU-UHFFFAOYSA-N 0.000 description 1
- KCMITHMNVLRGJU-CMDGGOBGSA-N Allyl cinnamate Chemical compound C=CCOC(=O)\C=C\C1=CC=CC=C1 KCMITHMNVLRGJU-CMDGGOBGSA-N 0.000 description 1
- DWVYLJALYRFSKO-UHFFFAOYSA-N COC(OC)[SiH2]CCCC(C)(C)C(O)=O Chemical compound COC(OC)[SiH2]CCCC(C)(C)C(O)=O DWVYLJALYRFSKO-UHFFFAOYSA-N 0.000 description 1
- VTXCYUSDHZKYIF-UHFFFAOYSA-N Cl[SiH](Cl)C1=CC=C(Cl)C=C1 Chemical compound Cl[SiH](Cl)C1=CC=C(Cl)C=C1 VTXCYUSDHZKYIF-UHFFFAOYSA-N 0.000 description 1
- 238000003479 Claisen-Ireland rearrangement reaction Methods 0.000 description 1
- 238000006568 Claisen-Johnson rearrangement reaction Methods 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 241000546339 Trioxys Species 0.000 description 1
- GSKVLVXXJRJNAN-UHFFFAOYSA-N [di(propan-2-yl)-$l^{3}-silanyl]oxy-di(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)O[Si](C(C)C)C(C)C GSKVLVXXJRJNAN-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 238000005937 allylation reaction Methods 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SKDKWDVYZOKBPL-UHFFFAOYSA-N benzyl(dimethyl)silicon Chemical compound C[Si](C)CC1=CC=CC=C1 SKDKWDVYZOKBPL-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- WEAGTHQEGNMQLU-UHFFFAOYSA-N chloro(diethyl)silane Chemical compound CC[SiH](Cl)CC WEAGTHQEGNMQLU-UHFFFAOYSA-N 0.000 description 1
- PAJFATIYVLZNFC-UHFFFAOYSA-N chloromethyl(dimethyl)silicon Chemical compound C[Si](C)CCl PAJFATIYVLZNFC-UHFFFAOYSA-N 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HVLLBACCZSTYCQ-UHFFFAOYSA-N cyclohex-3-en-1-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCC=CC1 HVLLBACCZSTYCQ-UHFFFAOYSA-N 0.000 description 1
- JFDSHJDHYXKJFG-UHFFFAOYSA-N cyclohexyl(dimethyl)silicon Chemical compound C[Si](C)C1CCCCC1 JFDSHJDHYXKJFG-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([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])[H] 0.000 description 1
- AHQMQQYLFHXPOE-UHFFFAOYSA-N decyl(dimethyl)silicon Chemical compound CCCCCCCCCC[Si](C)C AHQMQQYLFHXPOE-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000005548 dental material Substances 0.000 description 1
- JQZUMFHYRULBEN-UHFFFAOYSA-N diethyl(methyl)silicon Chemical compound CC[Si](C)CC JQZUMFHYRULBEN-UHFFFAOYSA-N 0.000 description 1
- UCXUKTLCVSGCNR-UHFFFAOYSA-N diethylsilane Chemical compound CC[SiH2]CC UCXUKTLCVSGCNR-UHFFFAOYSA-N 0.000 description 1
- DEHJVGGWPWZZHI-UHFFFAOYSA-N dimethyl(3,3,3-trifluoropropyl)silane Chemical compound C[SiH](C)CCC(F)(F)F DEHJVGGWPWZZHI-UHFFFAOYSA-N 0.000 description 1
- ZXFNVHQEUQDKSZ-UHFFFAOYSA-N dimethyl(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[SiH](C)C ZXFNVHQEUQDKSZ-UHFFFAOYSA-N 0.000 description 1
- OIKHZBFJHONJJB-UHFFFAOYSA-N dimethyl(phenyl)silicon Chemical compound C[Si](C)C1=CC=CC=C1 OIKHZBFJHONJJB-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- KJISMKWTHPWHFV-UHFFFAOYSA-N ethyl(dimethyl)silicon Chemical compound CC[Si](C)C KJISMKWTHPWHFV-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- FCKFHVFZPCZMDQ-UHFFFAOYSA-N hexyl(dimethyl)silane Chemical compound CCCCCC[SiH](C)C FCKFHVFZPCZMDQ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 150000002560 ketene acetals Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WQEWAQFTKKOSJK-UHFFFAOYSA-N methoxymethylsilane Chemical compound COC[SiH3] WQEWAQFTKKOSJK-UHFFFAOYSA-N 0.000 description 1
- OKHRRIGNGQFVEE-UHFFFAOYSA-N methyl(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](C)C1=CC=CC=C1 OKHRRIGNGQFVEE-UHFFFAOYSA-N 0.000 description 1
- OHSYWAVRSCQMHG-UHFFFAOYSA-N methyl-[methyl(trimethylsilyloxy)-$l^{3}-silanyl]oxy-trimethylsilyloxysilicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)O[Si](C)(C)C OHSYWAVRSCQMHG-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- PIZSEPSUZMIOQF-UHFFFAOYSA-N platinum;2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound [Pt].C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 PIZSEPSUZMIOQF-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- UBLMWQYLVOVZMT-UHFFFAOYSA-N tert-butyl n-(3-acetylphenyl)carbamate Chemical compound CC(=O)C1=CC=CC(NC(=O)OC(C)(C)C)=C1 UBLMWQYLVOVZMT-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- ISEIIPDWJVGTQS-UHFFFAOYSA-N tributylsilicon Chemical compound CCCC[Si](CCCC)CCCC ISEIIPDWJVGTQS-UHFFFAOYSA-N 0.000 description 1
- HUZZQXYTKNNCOU-UHFFFAOYSA-N triethyl(methoxy)silane Chemical compound CC[Si](CC)(CC)OC HUZZQXYTKNNCOU-UHFFFAOYSA-N 0.000 description 1
- JEZDAGARLVZEGB-UHFFFAOYSA-N triethylsilyl pentanoate Chemical compound CCCCC(=O)O[Si](CC)(CC)CC JEZDAGARLVZEGB-UHFFFAOYSA-N 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
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 1
- ZHOVAWFVVBWEGQ-UHFFFAOYSA-N tripropylsilane Chemical compound CCC[SiH](CCC)CCC ZHOVAWFVVBWEGQ-UHFFFAOYSA-N 0.000 description 1
- OXBITGHYUPJVFH-UHFFFAOYSA-N tris(2-methylphenyl)silane Chemical compound CC1=CC=CC=C1[SiH](C=1C(=CC=CC=1)C)C1=CC=CC=C1C OXBITGHYUPJVFH-UHFFFAOYSA-N 0.000 description 1
- GEUFMGZEFYJAEJ-UHFFFAOYSA-N tris(2-methylpropyl)silicon Chemical compound CC(C)C[Si](CC(C)C)CC(C)C GEUFMGZEFYJAEJ-UHFFFAOYSA-N 0.000 description 1
- ALKQPTICPBGBJJ-UHFFFAOYSA-N tris(4-methylphenyl)silane Chemical compound C1=CC(C)=CC=C1[SiH](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ALKQPTICPBGBJJ-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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 System
- 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
Description
γ,δ−不飽和カルボン酸及びそのエステルの製造方法として、(a)カルボン酸のα−炭素のアリル化、(b)γ,δ−不飽和アルデヒドの酸化、(c)Claisen転位等の方法が報告されている。
また、カルボキシル基を有する有機ケイ素化合物は、シランカップリング剤や種々の変性シリコーンオイル等の原料、あるいはポリアミドやポリエステル等重縮合ポリマーの原料として有用な化合物である。その製造方法として、例えば特開2001−158791号公報(特許文献5)や特開平11−193291号公報(特許文献6)にはカルボン酸及びカルボン酸エステル部位を有するシロキサンの製造方法が開示されている。どちらの場合にも、ケイ素−炭素結合を形成するためにヒドロシリル化反応を用いており、カルボキシル基又はその前駆体を有するケイ素化合物の合成には温和な反応であるヒドロシリル化が有効である。しかし、その原料となる不飽和カルボン酸及びその等価体で工業的に得られるものはきわめて限られている。従って、それを用いて製造されるカルボキシル基を有する有機ケイ素化合物の種類も限られており、満足のいくものではなく、この点の解決も望まれていた。
[I]下記一般式(1)で表されるα,β−不飽和カルボン酸エステルと、下記一般式(2)で表されるヒドロシラン又はヒドロシロキサンとを触媒量のトリス(ペンタフルオロフェニル)ボラン存在下に反応させることを特徴とする下記一般式(3)で表されるγ,δ−不飽和カルボン酸シリルエステルの製造方法。
上記式(1)で表されるα,β−不飽和カルボン酸エステルとして具体的には、アクリル酸アリル、メタクリル酸アリル、クロトン酸アリル、桂皮酸アリル、メタクリル酸メタリル、メタクリル酸3−シクロヘキセニル等が挙げられる。
また、RaとRb、RaとRc又はRbとRcは互いに結合してこれらが結合するケイ素原子と共に、ケイ素数3〜50、特に3〜20のシロキサン環又は炭素数1〜20のケイ素含有環を形成してもよい。また、Ra、Rb、Rcは互いに結合してこれらが結合するケイ素原子と共にケイ素数6〜50、特に6〜20のかご状シロキサンを形成してもよい。
Ra、Rb、Rcの具体例として、例えばメチル基、クロロメチル基、トリフルオロメチル基、エチル基、プロピル基、3−クロロプロピル基、3,3,3−トリフルオロプロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、ペンチル基、シクロペンチル基、ヘキシル基、シクロヘキシル基、オクチル基、デシル基、ドデシル基、ステアリル基等の直鎖状、分岐鎖状、環状の非置換もしくはハロゲン置換アルキル基、フェニル基、4−フルオロフェニル基、4−クロロフェニル基、4−ブロモフェニル基、4−ヨードフェニル基、ペンタフルオロフェニル基、トリル基、キシリル基、ナフチル基、ビフェニリル基等の非置換もしくはハロゲン置換アリール基、ベンジル基、フェニルエチル基、フェニルプロピル基等の非置換もしくはハロゲン置換アラルキル基、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、sec−ブトキシ基、tert−ブトキシ基、イソブトキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、ノルボルニルオキシ基等の非置換もしくはハロゲン置換アルコキシ基、フェノキシ基、3−クロロフェノキシ基、ナフチルオキシ基等の非置換もしくはハロゲン置換アリールオキシ基、ベンジルオキシ基、2−クロロベンジルオキシ基、3−クロロベンジルオキシ基、4−クロロベンジルオキシ基、ナフチルエチルオキシ基等の非置換もしくはハロゲン置換アラルキルオキシ基、ジメチルシロキシ基、ジエチルシロキシ基、ジフェニルシロキシ基、トリメチルシロキシ基、クロロメチルジメチルシロキシ基、トリエチルシロキシ基、フェニルジメチルシロキシ基、ジフェニルメチルシロキシ基、1,1,3,3,3−ペンタメチルジシロキサニルオキシ基、1,1,3,3−テトラメチルジシロキサニルオキシ基、ω−メチルポリジメチルシロキサニルオキシ基、ω−ヒドロポリジメチルシロキサニルオキシ基、ポリヒドロメチルシロキサニルオキシ基、メチルビス(トリメチルシロキシ)シロキシ基、メチルビス(ジメチルシロキシ)シロキシ基、トリス(トリメチルシロキシ)シロキシ基、1,3,3,5,5−ペンタメチルシクロトリシロキサン−1−イルオキシ基、1,3,5−トリメチル−3,5−ビス(3,3,3−トリフルオロプロピル)シクロトリシロキサン−1−イルオキシ基、1,3,5,7−テトラメチルシクロテトラシロキサン−1−イルオキシ基等の直鎖状、分岐鎖状、環状のケイ素原子数1〜1,000、特に1〜200の(ポリ)オルガノシロキシ基等が挙げられる。
Rgは水酸基、炭素数1〜20、好ましくは1〜10のアルコキシ基、炭素数6〜20、好ましくは6〜12のアリールオキシ基、炭素数7〜20、好ましくは7〜14のアラルキルオキシ基、ケイ素原子に結合した基が炭素数1〜20、好ましくは1〜18の非置換又は置換一価炭化水素基又は水素原子であるケイ素原子数1〜1,000、好ましくは1〜200のオルガノシロキシ基、ハロゲン原子から選ばれる基を表す。Rh、Riはそれぞれ独立に水酸基、炭素数1〜20、好ましくは1〜18のアルキル基、炭素数6〜20、好ましくは6〜12のアリール基、炭素数7〜20、好ましくは7〜14のアラルキル基、炭素数1〜20、好ましくは1〜10のアルコキシ基、炭素数6〜20、好ましくは6〜12のアリールオキシ基、炭素数7〜20、好ましくは7〜14のアラルキルオキシ基、ケイ素原子に結合した基がそれぞれ炭素数1〜20、好ましくは1〜18の非置換又は置換一価炭化水素基又は水素原子であるケイ素原子数1〜1,000、好ましくは1〜200のオルガノシロキシ基、ハロゲン原子から選ばれる基を表す。この場合、上記ケイ素原子に結合した非置換又は置換一価炭化水素基としては、アルキル基、アリール基等やこれらの基の水素原子の一部又は全部がハロゲン原子、水酸基、カルボキシル基、トリアルキルシロキシカルボニル基等のトリオルガノシロキシカルボニル基で置換された基が例示される。Rg、Rh、Riはヒドロシリル化(特に白金触媒による)を受ける不飽和結合を含有しない置換基を有していてもよく、RgとRh、RgとRi又はRhとRiは互いに結合してこれらが結合するケイ素原子と共に、ケイ素数3〜50、特に3〜20のシロキサン環又は炭素数1〜20のケイ素含有環を形成してもよい。また、Rg、Rh、Riは互いに結合してこれらが結合するケイ素原子と共にケイ素数6〜50、特に6〜20のかご状シロキサンを形成してもよい。
ジムロート式還流冷却器、撹拌機、温度計、滴下ロートを備えた300mLの四つ口フラスコを窒素置換した。トリス(ペンタフルオロフェニル)ボラン(アルドリッチ製、ロットNo.18609AO、以下同様)25.6mg(0.050mmol)、1,3,5−トリス(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)−2,4,6−トリメチルベンゼン(以下、イルガノックス1330、チバ・スペシャルティー・ケミカルズ社製)1.29g、トリエチルシラン58.2g(0.50mol)を仕込み、室温で0.5時間撹拌した。オイルバスでフラスコを加熱して内温を40℃に調整し、メタクリル酸アリル37.9g(0.30mol)を滴下ロートから2時間かけて滴下した。滴下に伴って発熱が見られ、内温が40〜50℃に保たれるように加熱を調整した。トリス(ペンタフルオロフェニル)ボラン12.8mg(0.025mmol)を10%トルエン溶液として添加した後、更にメタクリル酸アリル25.2g(0.20mol)を滴下ロートより1.2時間、40−50℃で滴下した。滴下終了から5分後、ガスクロマトグラフィーによりトリエチルシランが消失していることが確認された。無色透明の反応液を減圧蒸留し、沸点が74.5〜76.5℃/0.3kPaの無色透明液体115.9gを得た。NMRスペクトル及びGC/MSスペクトルの測定結果から、この液体は目的の2,2−ジメチル−4−ペンテン酸トリエチルシリルと同定された。収率は95.6%であった。
13C−NMR(CDCl3,75.6MHz):δ(ppm)178.0,134.4,117.7,44.7,43.2,24.9,6.5,4.5
MS(EI):m/z 242(M+),213,172,115,87,75
ジムロート式還流冷却器、撹拌機、温度計、滴下ロートを備えた100mLの四つ口フラスコを窒素置換した。フラスコ内にBHT220mg、トルエン5mL、及びトリス(ペンタフルオロフェニル)ボラン2.6mg(0.005mmol)の10%トルエン溶液を仕込み、内容物を撹拌しながら氷水浴で4℃に冷却した。メタクリル酸アリル12.6g(0.10mol)とエトキシジメチルシラン10.4g(0.10mol)の混合液を滴下ロートから3.5時間かけて滴下した。内温は最高12℃まで上昇した。滴下終了後、4℃で2時間撹拌を続けた。その後トリエチルアミン7μL(0.05mmol)を加え、反応混合物を減圧蒸留した。沸点61〜62℃/0.7kPaの無色透明留分19.7gが得られ、NMR及びGC/MSの結果より、この液体は目的の2,2−ジメチル−4−ペンテン酸エトキシジメチルシリルであると同定された。収率は85.5%であった。
13C−NMR(CDCl3,75.6MHz):δ(ppm)177.5,134.2,117.8,59.1,44.7,43.1,24.7,18.2,−2.4
MS(EI):m/z 230(M+),215,185,184,174,103,75
ジムロート式還流冷却器、撹拌機、温度計、滴下ロートを備えた100mLの四つ口フラスコを窒素置換した。フラスコ内にBHT220mg、トルエン5mL、及びトリス(ペンタフルオロフェニル)ボラン51mg(0.10mmol)を仕込み、内容物を撹拌しながら氷水浴で2.5℃に冷却した。メタクリル酸アリル12.6g(0.10mol)とクロロジメチルシラン9.5g(0.10mol)の混合液を滴下ロートから3.5時間かけて滴下した。内温は最高12℃まで上昇した。滴下終了後、2℃で2時間撹拌を続けた。わずかに黄色の反応混合物を減圧蒸留した。沸点70〜70.5℃/1.2kPaの無色透明留分16.1gが得られ、NMR及びGC/MSの結果より、この液体は目的の2,2−ジメチル−4−ペンテン酸クロロジメチルシリルであると同定された。収率は72.9%であった。
13C−NMR(CDCl3,75.6MHz):δ(ppm)177.0,133.8,118.2,44.5,43.2,24.5,2.5
MS(EI):m/z 222,220(M+),207,205,185,95,93,83,82,55,41
ジムロート式還流冷却器、撹拌機、温度計、滴下ロートを備えた100mLの四つ口フラスコを窒素置換した。フラスコ内にイルガノックス1330を258mg、トリス(ペンタフルオロフェニル)ボランを2.6mg(0.005mmol)、及びトルエン5mLを仕込み、内容物を撹拌した。フラスコを水浴で冷却し、メタクリル酸アリル63.1g(0.50mol)と1,1,3,3−テトラメチルジシロキサン33.6g(0.50mol)の混合液を9時間かけて内温1.5〜12℃で滴下した。1,1,3,3−テトラメチルジシロキサンの消失がGCにより確認された。滴下終了後、更に2〜4℃で3時間撹拌を続けたところ、無色透明の反応混合物が得られ、これを減圧蒸留した。沸点101.5〜103.5℃/0.2kPaの無色透明留分91.6gが得られ、NMR及びGC/MSの結果より、この液体は目的の1,3−ビス(2,2−ジメチル−4−ペンテノイルオキシ)−1,1,3,3−テトラメチルジシロキサンであると同定された。収率は94.8%であった。
13C−NMR(CDCl3,75.6MHz):δ(ppm)177.3,134.2,117.9,44.6,43.0,24.7,−0.5
MS(EI):m/z 386(M+),371,259,133,83,55,41
ジムロート式還流冷却器、撹拌機、温度計を備えた100mLの四つ口フラスコを窒素置換した。フラスコ内に2,2−ジメチル−4−ペンテン酸エトキシジメチルシリル17.7g(0.0768mol)及びエタノール14.2g(0.307mol)を仕込み、室温で1時間、60〜65℃で5時間撹拌した。反応混合物を減圧蒸留したところ、沸点78〜79℃/0.6kPaの無色透明留分9.2gが得られ、NMR及びGC/MSの結果より、この液体は目的の2,2−ジメチル−4−ペンテン酸であると同定された。収率は93.4%であった。
13C−NMR(CDCl3,75.6MHz):δ(ppm)184.6,133.9,118.2,44.4,42.2,24.5
MS(EI):m/z 128(M+),113,83,55,41
ジムロート式還流冷却器、撹拌機、温度計、滴下ロートを備えた100mLの四つ口フラスコを窒素置換した。フラスコ内にBHT25mg、トリス(ペンタフルオロフェニル)ボラン5.1mg(0.01mmol)、トリエチルシラン11.6g(0.1mol)を仕込み、内容物を室温で0.5時間撹拌した後、氷水浴で10℃に冷却した。メタクリル酸アリル10.1g(0.08mol)を滴下ロートから2時間かけて滴下した。内温は最高18℃まで上昇した。トリス(ペンタフルオロフェニル)ボラン1mg(0.002mmol)を10%トルエン溶液として加え、メタクリル酸アリル2.5g(0.02mol)を0.5時間、10〜18℃で滴下した。滴下終了後、10℃で2時間撹拌を続けたところ、トリエチルシランが消失し、2,2−ジメチル−4−ペンテン酸トリエチルシリルが生成したことがGCによって確認された。
この反応混合物に、白金(0)テトラメチルジビニルジシロキサン錯体のトルエン溶液(白金3質量%)32.5mg(Pt5μmol)を加え、撹拌しながらオイルバスで60℃に内温を調節した。トリエトキシシラン16.4g(0.10mol)を3.5時間かけて滴下した。内温は最高70℃まで上昇した。滴下終了後、70℃に温度を上げて6時間熟成したところ、トリエトキシシランの転化率は99.5%以上に達した。得られた淡黄橙色の反応混合物を減圧蒸留した。沸点152〜153℃/0.3kPaの無色透明留分33.1gが得られ、NMR及びGC/MSの結果より、この液体は目的の2,2−ジメチル−5−(トリエトキシシリル)ペンタン酸トリエチルシリルであると同定された。収率は81.4%であった。
13C−NMR(CDCl3,75.6MHz):δ(ppm)178.6,58.3,44.4,43.3,25.2,18.4,18.2,11.1,6.5,4.5
29Si−NMR(CDCl3,59.7MHz):δ(ppm)24.6,−45.4
MS(EI):m/z 406(M+),377,361,360,317,303,265,257,221,202,172,163,157,119,115,87
ジムロート式還流冷却器、撹拌機、温度計、滴下ロートを備えた100mLの四つ口フラスコを窒素置換した。フラスコ内にBHT25mg、トリス(ペンタフルオロフェニル)ボラン5.1mg(0.01mmol)、トリエチルシラン11.6g(0.1mol)を仕込み、内容物を室温で0.5時間撹拌した後、水浴で21℃に冷却した。メタクリル酸アリル7.6g(0.06mol)を滴下ロートから1.5時間かけて滴下した。内温は最高28℃まで上昇した。トリス(ペンタフルオロフェニル)ボラン1mg(0.002mmol)を10%トルエン溶液として加えた後、メタクリル酸アリル5.0g(0.04mol)を1時間、22〜26℃で滴下した。滴下終了から0.5時間撹拌を続けたところ、トリエチルシランが消失し、2,2−ジメチル−4−ペンテン酸トリエチルシリルが生成したことがGCによって確認された。
この反応混合物に、白金(0)テトラメチルジビニルジシロキサン錯体のトルエン溶液(白金3質量%)32.5mg(Pt5μmol)を加え、撹拌しながらオイルバスで46℃に内温を調節した。ジメトキシメチルシラン10.6g(0.10mol)を3.5時間かけて滴下した。内温は最高58℃まで上昇した。滴下終了後、49〜58℃で5時間熟成したところ、ジメトキシメチルシランの転化率は99.5%以上に達した。得られた黄色の反応混合物を減圧蒸留した。沸点129〜130℃/0.2kPaの無色透明留分29.5gが得られ、NMR及びGC/MSの結果より、この液体は目的の2,2−ジメチル−5−(ジメトキシメチルシリル)ペンタン酸トリエチルシリルであると同定された。収率は84.6%であった。
13C−NMR(CDCl3,75.6MHz):δ(ppm)178.3,49.9,44.4,43.2,25.1,18.2,13.6,6.3,4.4,−6.0
29Si−NMR(CDCl3,59.7MHz):δ(ppm)24.6,−1.6
MS(EI):m/z 319([M−Et]+),259,207,202,177,172,157,115,105,87,75,59
ジムロート式還流冷却器、撹拌機、温度計、滴下ロートを備えた100mLの四つ口フラスコを窒素置換した。フラスコ内にBHT220mg、トリス(ペンタフルオロフェニル)ボラン5.1mg(0.01mmol)、トリエチルシラン11.6g(0.1mol)を仕込み、内容物を室温で0.25時間撹拌した後、オイルバスで40℃に加熱した。メタクリル酸アリル8.8g(0.07mol)を滴下ロートから1.5時間かけて滴下した。内温が40〜50℃となるように加熱を調整した。トリス(ペンタフルオロフェニル)ボラン2mg(0.004mmol)を10%トルエン溶液として加えた後、メタクリル酸アリル3.8g(0.03mol)を0.5時間、42〜49℃で滴下した。滴下終了から0.5時間撹拌を続けたところ、トリエチルシランが消失し、2,2−ジメチル−4−ペンテン酸トリエチルシリルが生成したことがGCによって確認された。
この反応混合物に、白金(0)テトラメチルジビニルジシロキサン錯体のトルエン溶液(白金3質量%)32.5mg(Pt5μmol)を加え、撹拌しながらオイルバスで52℃に内温を調節した。エトキシジメチルシラン5.2g(0.05mol)を1時間かけて滴下した。内温は最高58℃まで上昇した。白金(0)テトラメチルジビニルジシロキサン錯体のトルエン溶液(白金3質量%)32.5mg(Pt5μmol)を追加し、エトキシジメチルシラン5.9g(0.057mol)を2時間かけて滴下した。滴下終了後、55〜59℃で10時間熟成したところ、エトキシジメチルシランの転化率は99.5%以上に達した。得られた黄橙色の反応混合物を減圧蒸留した。沸点128〜130.5℃/0.2kPaの無色透明留分29.3gが得られ、NMR及びGC/MSの結果より、この液体は目的の2,2−ジメチル−5−(エトキシジメチルシリル)ペンタン酸トリエチルシリルであると同定された。収率は84.4%(対トリエチルシラン)であった。
13C−NMR(CDCl3,75.6MHz):δ(ppm)178.4,58.0,44.7,43.2,25.1,18.7,18.4,17.0,6.4,4.5,2.2
29Si−NMR(CDCl3,59.7MHz):δ(ppm)24.6,16.7
MS(EI):m/z 346(M+),317,257,219,205,202,187,172,161,157,115,103,87,75,59
ジムロート式還流冷却器、撹拌機、温度計、滴下ロートを備えた100mLの四つ口フラスコを窒素置換した。フラスコ内に2,2−ジメチル−5−(エトキシジメチルシリル)ペンタン酸トリエチルシリル17.3g(50mmol)を仕込み、撹拌しながら滴下ロートより28%ナトリウムメトキシド−メタノール溶液9.6g(50mmol)を室温下15分で滴下した。1時間撹拌を続けた後、フラスコを徐々に加熱しながら減圧ストリップを行い、生成したトリエチルメトキシシランを除去した。2,2−ジメチル−5−(エトキシジメチルシリル)ペンタン酸トリエチルシリルの消失がGCにより確認され、2,2−ジメチル−5−(エトキシジメチルシリル)ペンタン酸がナトリウム塩として得られた。この淡黄色の固体残渣に36%塩酸10.1gを5分間かけて滴下し、スラリー状の混合物を撹拌しながら97〜102℃で4時間加熱還流させた。混合物を室温に冷却した後、酢酸エチル15mLと水10mLを加えて分液し、有機層を水10mLで洗浄後、減圧下で溶媒を除去し、乾燥することにより、9.3gの白色固体が得られた。
NMR及びMSスペクトル測定により、この固体は目的の1,3−ビス(4−カルボキシ−4−メチルペンチル)−1,1,3,3−テトラメチルジシロキサンであると同定された。収率は95.2%であった。
13C−NMR(CDCl3,75.6MHz):δ(ppm)185.2,45.6,42.2,24.9,18.8,18.6,0.3
29Si−NMR(CDCl3:59.7MHz):δ(ppm)7.2
MS(EI):m/z 261,245,187,149,133
MS(CI イソブタン):m/z 391([M+H]+),373,261,201,187
Claims (8)
- 下記一般式(1)で表されるα,β−不飽和カルボン酸エステルと、下記一般式(2)で表されるヒドロシラン又はヒドロシロキサンとを触媒量のトリス(ペンタフルオロフェニル)ボラン存在下に反応させることを特徴とする下記一般式(3)で表されるγ,δ−不飽和カルボン酸シリルエステルの製造方法。
- 下記一般式(5)で表される、シリル化されたカルボキシル基を有する有機ケイ素化合物。
- 上記一般式(5)において、R1、R2、R4、R4'、R5、R6、R6'が水素原子、R3がメチル基である、請求項3に記載のシリル化されたカルボキシル基を有する有機ケイ素化合物。
- 請求項1に記載の方法により得られた一般式(3)で表されるγ,δ−不飽和カルボン酸シリルエステルを、下記一般式(6)で表されるヒドロシラン又はヒドロシロキサンを用いてヒドロシリル化することを特徴とする下記一般式(5)で表されるシリル化されたカルボキシル基を有する有機ケイ素化合物の製造方法。
- 下記一般式(7)で表される、カルボキシル基を有する有機ケイ素化合物。
- 上記一般式(7)において、R1、R2、R4、R4'、R5、R6、R6'が水素原子、R3がメチル基である、請求項6に記載のシリル化されたカルボキシル基を有する有機ケイ素化合物。
- 下記一般式(5)で表される、シリル化されたカルボキシル基を有する有機ケイ素化合物を脱シリル化することを特徴とする下記一般式(7)で表されるカルボキシル基を有する有機ケイ素化合物の製造方法。
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003333014A JP4524554B2 (ja) | 2003-09-25 | 2003-09-25 | γ,δ−不飽和カルボン酸及びそのシリルエステルの製造方法、カルボキシル基を有する有機ケイ素化合物及びその製造方法 |
US10/947,129 US7307178B2 (en) | 2003-09-25 | 2004-09-23 | Processes of making γ,δ-unsaturated carboxylic acid and silyl ester thereof, carboxyl group-containing organosilicon compound and process of making |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003333014A JP4524554B2 (ja) | 2003-09-25 | 2003-09-25 | γ,δ−不飽和カルボン酸及びそのシリルエステルの製造方法、カルボキシル基を有する有機ケイ素化合物及びその製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005097173A JP2005097173A (ja) | 2005-04-14 |
JP4524554B2 true JP4524554B2 (ja) | 2010-08-18 |
Family
ID=34373112
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003333014A Expired - Fee Related JP4524554B2 (ja) | 2003-09-25 | 2003-09-25 | γ,δ−不飽和カルボン酸及びそのシリルエステルの製造方法、カルボキシル基を有する有機ケイ素化合物及びその製造方法 |
Country Status (2)
Country | Link |
---|---|
US (1) | US7307178B2 (ja) |
JP (1) | JP4524554B2 (ja) |
Families Citing this family (329)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008505185A (ja) * | 2004-07-02 | 2008-02-21 | ハネウェル・インターナショナル・インコーポレーテッド | 官能基化ケイ素化合物 |
JP5175576B2 (ja) * | 2008-02-15 | 2013-04-03 | 東レ・ダウコーニング株式会社 | 両末端(メタ)アクリロキシプロピル基封鎖ジオルガノポリシロキサンの製造方法 |
US10378106B2 (en) | 2008-11-14 | 2019-08-13 | Asm Ip Holding B.V. | Method of forming insulation film by modified PEALD |
US9394608B2 (en) | 2009-04-06 | 2016-07-19 | Asm America, Inc. | Semiconductor processing reactor and components thereof |
US8802201B2 (en) | 2009-08-14 | 2014-08-12 | Asm America, Inc. | Systems and methods for thin-film deposition of metal oxides using excited nitrogen-oxygen species |
US8329599B2 (en) | 2011-02-18 | 2012-12-11 | Asm Japan K.K. | Method of depositing dielectric film by ALD using precursor containing silicon, hydrocarbon, and halogen |
US8563443B2 (en) | 2011-02-18 | 2013-10-22 | Asm Japan K.K. | Method of depositing dielectric film by ALD using precursor containing silicon, hydrocarbon, and halogen |
US9312155B2 (en) | 2011-06-06 | 2016-04-12 | Asm Japan K.K. | High-throughput semiconductor-processing apparatus equipped with multiple dual-chamber modules |
US9793148B2 (en) | 2011-06-22 | 2017-10-17 | Asm Japan K.K. | Method for positioning wafers in multiple wafer transport |
US10364496B2 (en) | 2011-06-27 | 2019-07-30 | Asm Ip Holding B.V. | Dual section module having shared and unshared mass flow controllers |
US10854498B2 (en) | 2011-07-15 | 2020-12-01 | Asm Ip Holding B.V. | Wafer-supporting device and method for producing same |
US20130023129A1 (en) | 2011-07-20 | 2013-01-24 | Asm America, Inc. | Pressure transmitter for a semiconductor processing environment |
US9017481B1 (en) | 2011-10-28 | 2015-04-28 | Asm America, Inc. | Process feed management for semiconductor substrate processing |
US20130224964A1 (en) * | 2012-02-28 | 2013-08-29 | Asm Ip Holding B.V. | Method for Forming Dielectric Film Containing Si-C bonds by Atomic Layer Deposition Using Precursor Containing Si-C-Si bond |
US8946830B2 (en) | 2012-04-04 | 2015-02-03 | Asm Ip Holdings B.V. | Metal oxide protective layer for a semiconductor device |
US9558931B2 (en) | 2012-07-27 | 2017-01-31 | Asm Ip Holding B.V. | System and method for gas-phase sulfur passivation of a semiconductor surface |
US9659799B2 (en) | 2012-08-28 | 2017-05-23 | Asm Ip Holding B.V. | Systems and methods for dynamic semiconductor process scheduling |
US9021985B2 (en) | 2012-09-12 | 2015-05-05 | Asm Ip Holdings B.V. | Process gas management for an inductively-coupled plasma deposition reactor |
US9324811B2 (en) | 2012-09-26 | 2016-04-26 | Asm Ip Holding B.V. | Structures and devices including a tensile-stressed silicon arsenic layer and methods of forming same |
US10714315B2 (en) | 2012-10-12 | 2020-07-14 | Asm Ip Holdings B.V. | Semiconductor reaction chamber showerhead |
US9640416B2 (en) | 2012-12-26 | 2017-05-02 | Asm Ip Holding B.V. | Single-and dual-chamber module-attachable wafer-handling chamber |
US9484191B2 (en) | 2013-03-08 | 2016-11-01 | Asm Ip Holding B.V. | Pulsed remote plasma method and system |
US9589770B2 (en) | 2013-03-08 | 2017-03-07 | Asm Ip Holding B.V. | Method and systems for in-situ formation of intermediate reactive species |
US8993054B2 (en) | 2013-07-12 | 2015-03-31 | Asm Ip Holding B.V. | Method and system to reduce outgassing in a reaction chamber |
US9018111B2 (en) | 2013-07-22 | 2015-04-28 | Asm Ip Holding B.V. | Semiconductor reaction chamber with plasma capabilities |
US9793115B2 (en) | 2013-08-14 | 2017-10-17 | Asm Ip Holding B.V. | Structures and devices including germanium-tin films and methods of forming same |
US9240412B2 (en) | 2013-09-27 | 2016-01-19 | Asm Ip Holding B.V. | Semiconductor structure and device and methods of forming same using selective epitaxial process |
US9556516B2 (en) | 2013-10-09 | 2017-01-31 | ASM IP Holding B.V | Method for forming Ti-containing film by PEALD using TDMAT or TDEAT |
US10179947B2 (en) | 2013-11-26 | 2019-01-15 | Asm Ip Holding B.V. | Method for forming conformal nitrided, oxidized, or carbonized dielectric film by atomic layer deposition |
US10683571B2 (en) | 2014-02-25 | 2020-06-16 | Asm Ip Holding B.V. | Gas supply manifold and method of supplying gases to chamber using same |
US9447498B2 (en) | 2014-03-18 | 2016-09-20 | Asm Ip Holding B.V. | Method for performing uniform processing in gas system-sharing multiple reaction chambers |
US10167557B2 (en) | 2014-03-18 | 2019-01-01 | Asm Ip Holding B.V. | Gas distribution system, reactor including the system, and methods of using the same |
US11015245B2 (en) | 2014-03-19 | 2021-05-25 | Asm Ip Holding B.V. | Gas-phase reactor and system having exhaust plenum and components thereof |
US9404587B2 (en) | 2014-04-24 | 2016-08-02 | ASM IP Holding B.V | Lockout tagout for semiconductor vacuum valve |
US10858737B2 (en) | 2014-07-28 | 2020-12-08 | Asm Ip Holding B.V. | Showerhead assembly and components thereof |
US9543180B2 (en) | 2014-08-01 | 2017-01-10 | Asm Ip Holding B.V. | Apparatus and method for transporting wafers between wafer carrier and process tool under vacuum |
US9890456B2 (en) | 2014-08-21 | 2018-02-13 | Asm Ip Holding B.V. | Method and system for in situ formation of gas-phase compounds |
US10941490B2 (en) | 2014-10-07 | 2021-03-09 | Asm Ip Holding B.V. | Multiple temperature range susceptor, assembly, reactor and system including the susceptor, and methods of using the same |
US9657845B2 (en) | 2014-10-07 | 2017-05-23 | Asm Ip Holding B.V. | Variable conductance gas distribution apparatus and method |
KR102300403B1 (ko) | 2014-11-19 | 2021-09-09 | 에이에스엠 아이피 홀딩 비.브이. | 박막 증착 방법 |
KR102263121B1 (ko) | 2014-12-22 | 2021-06-09 | 에이에스엠 아이피 홀딩 비.브이. | 반도체 소자 및 그 제조 방법 |
US9478415B2 (en) | 2015-02-13 | 2016-10-25 | Asm Ip Holding B.V. | Method for forming film having low resistance and shallow junction depth |
US10529542B2 (en) | 2015-03-11 | 2020-01-07 | Asm Ip Holdings B.V. | Cross-flow reactor and method |
US10276355B2 (en) | 2015-03-12 | 2019-04-30 | Asm Ip Holding B.V. | Multi-zone reactor, system including the reactor, and method of using the same |
US10458018B2 (en) | 2015-06-26 | 2019-10-29 | Asm Ip Holding B.V. | Structures including metal carbide material, devices including the structures, and methods of forming same |
US10600673B2 (en) | 2015-07-07 | 2020-03-24 | Asm Ip Holding B.V. | Magnetic susceptor to baseplate seal |
US10043661B2 (en) | 2015-07-13 | 2018-08-07 | Asm Ip Holding B.V. | Method for protecting layer by forming hydrocarbon-based extremely thin film |
US9899291B2 (en) | 2015-07-13 | 2018-02-20 | Asm Ip Holding B.V. | Method for protecting layer by forming hydrocarbon-based extremely thin film |
US10083836B2 (en) | 2015-07-24 | 2018-09-25 | Asm Ip Holding B.V. | Formation of boron-doped titanium metal films with high work function |
US10087525B2 (en) | 2015-08-04 | 2018-10-02 | Asm Ip Holding B.V. | Variable gap hard stop design |
US9647114B2 (en) | 2015-08-14 | 2017-05-09 | Asm Ip Holding B.V. | Methods of forming highly p-type doped germanium tin films and structures and devices including the films |
US9711345B2 (en) | 2015-08-25 | 2017-07-18 | Asm Ip Holding B.V. | Method for forming aluminum nitride-based film by PEALD |
US9960072B2 (en) | 2015-09-29 | 2018-05-01 | Asm Ip Holding B.V. | Variable adjustment for precise matching of multiple chamber cavity housings |
US9909214B2 (en) | 2015-10-15 | 2018-03-06 | Asm Ip Holding B.V. | Method for depositing dielectric film in trenches by PEALD |
US10211308B2 (en) | 2015-10-21 | 2019-02-19 | Asm Ip Holding B.V. | NbMC layers |
US10322384B2 (en) | 2015-11-09 | 2019-06-18 | Asm Ip Holding B.V. | Counter flow mixer for process chamber |
US9455138B1 (en) | 2015-11-10 | 2016-09-27 | Asm Ip Holding B.V. | Method for forming dielectric film in trenches by PEALD using H-containing gas |
US9905420B2 (en) | 2015-12-01 | 2018-02-27 | Asm Ip Holding B.V. | Methods of forming silicon germanium tin films and structures and devices including the films |
US9607837B1 (en) | 2015-12-21 | 2017-03-28 | Asm Ip Holding B.V. | Method for forming silicon oxide cap layer for solid state diffusion process |
US9627221B1 (en) | 2015-12-28 | 2017-04-18 | Asm Ip Holding B.V. | Continuous process incorporating atomic layer etching |
US9735024B2 (en) | 2015-12-28 | 2017-08-15 | Asm Ip Holding B.V. | Method of atomic layer etching using functional group-containing fluorocarbon |
US11139308B2 (en) | 2015-12-29 | 2021-10-05 | Asm Ip Holding B.V. | Atomic layer deposition of III-V compounds to form V-NAND devices |
US9754779B1 (en) | 2016-02-19 | 2017-09-05 | Asm Ip Holding B.V. | Method for forming silicon nitride film selectively on sidewalls or flat surfaces of trenches |
US10529554B2 (en) | 2016-02-19 | 2020-01-07 | Asm Ip Holding B.V. | Method for forming silicon nitride film selectively on sidewalls or flat surfaces of trenches |
US10468251B2 (en) | 2016-02-19 | 2019-11-05 | Asm Ip Holding B.V. | Method for forming spacers using silicon nitride film for spacer-defined multiple patterning |
US10501866B2 (en) | 2016-03-09 | 2019-12-10 | Asm Ip Holding B.V. | Gas distribution apparatus for improved film uniformity in an epitaxial system |
US10343920B2 (en) | 2016-03-18 | 2019-07-09 | Asm Ip Holding B.V. | Aligned carbon nanotubes |
US9892913B2 (en) | 2016-03-24 | 2018-02-13 | Asm Ip Holding B.V. | Radial and thickness control via biased multi-port injection settings |
US10087522B2 (en) | 2016-04-21 | 2018-10-02 | Asm Ip Holding B.V. | Deposition of metal borides |
US10865475B2 (en) | 2016-04-21 | 2020-12-15 | Asm Ip Holding B.V. | Deposition of metal borides and silicides |
US10190213B2 (en) | 2016-04-21 | 2019-01-29 | Asm Ip Holding B.V. | Deposition of metal borides |
US10367080B2 (en) | 2016-05-02 | 2019-07-30 | Asm Ip Holding B.V. | Method of forming a germanium oxynitride film |
US10032628B2 (en) | 2016-05-02 | 2018-07-24 | Asm Ip Holding B.V. | Source/drain performance through conformal solid state doping |
KR102592471B1 (ko) | 2016-05-17 | 2023-10-20 | 에이에스엠 아이피 홀딩 비.브이. | 금속 배선 형성 방법 및 이를 이용한 반도체 장치의 제조 방법 |
US11453943B2 (en) | 2016-05-25 | 2022-09-27 | Asm Ip Holding B.V. | Method for forming carbon-containing silicon/metal oxide or nitride film by ALD using silicon precursor and hydrocarbon precursor |
US10388509B2 (en) | 2016-06-28 | 2019-08-20 | Asm Ip Holding B.V. | Formation of epitaxial layers via dislocation filtering |
US9859151B1 (en) | 2016-07-08 | 2018-01-02 | Asm Ip Holding B.V. | Selective film deposition method to form air gaps |
US10612137B2 (en) | 2016-07-08 | 2020-04-07 | Asm Ip Holdings B.V. | Organic reactants for atomic layer deposition |
US9793135B1 (en) | 2016-07-14 | 2017-10-17 | ASM IP Holding B.V | Method of cyclic dry etching using etchant film |
US10714385B2 (en) | 2016-07-19 | 2020-07-14 | Asm Ip Holding B.V. | Selective deposition of tungsten |
KR102354490B1 (ko) | 2016-07-27 | 2022-01-21 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 방법 |
US9812320B1 (en) | 2016-07-28 | 2017-11-07 | Asm Ip Holding B.V. | Method and apparatus for filling a gap |
US10395919B2 (en) | 2016-07-28 | 2019-08-27 | Asm Ip Holding B.V. | Method and apparatus for filling a gap |
US9887082B1 (en) | 2016-07-28 | 2018-02-06 | Asm Ip Holding B.V. | Method and apparatus for filling a gap |
KR102532607B1 (ko) | 2016-07-28 | 2023-05-15 | 에이에스엠 아이피 홀딩 비.브이. | 기판 가공 장치 및 그 동작 방법 |
US10177025B2 (en) | 2016-07-28 | 2019-01-08 | Asm Ip Holding B.V. | Method and apparatus for filling a gap |
US10090316B2 (en) | 2016-09-01 | 2018-10-02 | Asm Ip Holding B.V. | 3D stacked multilayer semiconductor memory using doped select transistor channel |
US10410943B2 (en) | 2016-10-13 | 2019-09-10 | Asm Ip Holding B.V. | Method for passivating a surface of a semiconductor and related systems |
US10643826B2 (en) | 2016-10-26 | 2020-05-05 | Asm Ip Holdings B.V. | Methods for thermally calibrating reaction chambers |
JP6942459B2 (ja) * | 2016-10-27 | 2021-09-29 | 信越化学工業株式会社 | カルボン酸シリルエステル基含有アルコキシシラン化合物およびその製造方法 |
US11532757B2 (en) | 2016-10-27 | 2022-12-20 | Asm Ip Holding B.V. | Deposition of charge trapping layers |
US10643904B2 (en) | 2016-11-01 | 2020-05-05 | Asm Ip Holdings B.V. | Methods for forming a semiconductor device and related semiconductor device structures |
US10435790B2 (en) | 2016-11-01 | 2019-10-08 | Asm Ip Holding B.V. | Method of subatmospheric plasma-enhanced ALD using capacitively coupled electrodes with narrow gap |
US10714350B2 (en) | 2016-11-01 | 2020-07-14 | ASM IP Holdings, B.V. | Methods for forming a transition metal niobium nitride film on a substrate by atomic layer deposition and related semiconductor device structures |
US10229833B2 (en) | 2016-11-01 | 2019-03-12 | Asm Ip Holding B.V. | Methods for forming a transition metal nitride film on a substrate by atomic layer deposition and related semiconductor device structures |
US10134757B2 (en) | 2016-11-07 | 2018-11-20 | Asm Ip Holding B.V. | Method of processing a substrate and a device manufactured by using the method |
KR102546317B1 (ko) | 2016-11-15 | 2023-06-21 | 에이에스엠 아이피 홀딩 비.브이. | 기체 공급 유닛 및 이를 포함하는 기판 처리 장치 |
US10340135B2 (en) | 2016-11-28 | 2019-07-02 | Asm Ip Holding B.V. | Method of topologically restricted plasma-enhanced cyclic deposition of silicon or metal nitride |
KR20180068582A (ko) | 2016-12-14 | 2018-06-22 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 |
US9916980B1 (en) | 2016-12-15 | 2018-03-13 | Asm Ip Holding B.V. | Method of forming a structure on a substrate |
US11447861B2 (en) | 2016-12-15 | 2022-09-20 | Asm Ip Holding B.V. | Sequential infiltration synthesis apparatus and a method of forming a patterned structure |
US11581186B2 (en) | 2016-12-15 | 2023-02-14 | Asm Ip Holding B.V. | Sequential infiltration synthesis apparatus |
KR20180070971A (ko) | 2016-12-19 | 2018-06-27 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 |
US10269558B2 (en) | 2016-12-22 | 2019-04-23 | Asm Ip Holding B.V. | Method of forming a structure on a substrate |
US10867788B2 (en) | 2016-12-28 | 2020-12-15 | Asm Ip Holding B.V. | Method of forming a structure on a substrate |
US11390950B2 (en) | 2017-01-10 | 2022-07-19 | Asm Ip Holding B.V. | Reactor system and method to reduce residue buildup during a film deposition process |
US10655221B2 (en) | 2017-02-09 | 2020-05-19 | Asm Ip Holding B.V. | Method for depositing oxide film by thermal ALD and PEALD |
US10468261B2 (en) | 2017-02-15 | 2019-11-05 | Asm Ip Holding B.V. | Methods for forming a metallic film on a substrate by cyclical deposition and related semiconductor device structures |
US10283353B2 (en) | 2017-03-29 | 2019-05-07 | Asm Ip Holding B.V. | Method of reforming insulating film deposited on substrate with recess pattern |
US10529563B2 (en) | 2017-03-29 | 2020-01-07 | Asm Ip Holdings B.V. | Method for forming doped metal oxide films on a substrate by cyclical deposition and related semiconductor device structures |
US10103040B1 (en) | 2017-03-31 | 2018-10-16 | Asm Ip Holding B.V. | Apparatus and method for manufacturing a semiconductor device |
USD830981S1 (en) | 2017-04-07 | 2018-10-16 | Asm Ip Holding B.V. | Susceptor for semiconductor substrate processing apparatus |
KR102457289B1 (ko) | 2017-04-25 | 2022-10-21 | 에이에스엠 아이피 홀딩 비.브이. | 박막 증착 방법 및 반도체 장치의 제조 방법 |
US10892156B2 (en) | 2017-05-08 | 2021-01-12 | Asm Ip Holding B.V. | Methods for forming a silicon nitride film on a substrate and related semiconductor device structures |
US10446393B2 (en) | 2017-05-08 | 2019-10-15 | Asm Ip Holding B.V. | Methods for forming silicon-containing epitaxial layers and related semiconductor device structures |
US10770286B2 (en) | 2017-05-08 | 2020-09-08 | Asm Ip Holdings B.V. | Methods for selectively forming a silicon nitride film on a substrate and related semiconductor device structures |
US10504742B2 (en) | 2017-05-31 | 2019-12-10 | Asm Ip Holding B.V. | Method of atomic layer etching using hydrogen plasma |
US10886123B2 (en) | 2017-06-02 | 2021-01-05 | Asm Ip Holding B.V. | Methods for forming low temperature semiconductor layers and related semiconductor device structures |
US11306395B2 (en) | 2017-06-28 | 2022-04-19 | Asm Ip Holding B.V. | Methods for depositing a transition metal nitride film on a substrate by atomic layer deposition and related deposition apparatus |
US10685834B2 (en) | 2017-07-05 | 2020-06-16 | Asm Ip Holdings B.V. | Methods for forming a silicon germanium tin layer and related semiconductor device structures |
KR20190009245A (ko) | 2017-07-18 | 2019-01-28 | 에이에스엠 아이피 홀딩 비.브이. | 반도체 소자 구조물 형성 방법 및 관련된 반도체 소자 구조물 |
US10541333B2 (en) | 2017-07-19 | 2020-01-21 | Asm Ip Holding B.V. | Method for depositing a group IV semiconductor and related semiconductor device structures |
US11374112B2 (en) | 2017-07-19 | 2022-06-28 | Asm Ip Holding B.V. | Method for depositing a group IV semiconductor and related semiconductor device structures |
US11018002B2 (en) | 2017-07-19 | 2021-05-25 | Asm Ip Holding B.V. | Method for selectively depositing a Group IV semiconductor and related semiconductor device structures |
US10590535B2 (en) | 2017-07-26 | 2020-03-17 | Asm Ip Holdings B.V. | Chemical treatment, deposition and/or infiltration apparatus and method for using the same |
US10312055B2 (en) | 2017-07-26 | 2019-06-04 | Asm Ip Holding B.V. | Method of depositing film by PEALD using negative bias |
US10605530B2 (en) | 2017-07-26 | 2020-03-31 | Asm Ip Holding B.V. | Assembly of a liner and a flange for a vertical furnace as well as the liner and the vertical furnace |
US10692741B2 (en) | 2017-08-08 | 2020-06-23 | Asm Ip Holdings B.V. | Radiation shield |
US10770336B2 (en) | 2017-08-08 | 2020-09-08 | Asm Ip Holding B.V. | Substrate lift mechanism and reactor including same |
US10249524B2 (en) | 2017-08-09 | 2019-04-02 | Asm Ip Holding B.V. | Cassette holder assembly for a substrate cassette and holding member for use in such assembly |
US11139191B2 (en) | 2017-08-09 | 2021-10-05 | Asm Ip Holding B.V. | Storage apparatus for storing cassettes for substrates and processing apparatus equipped therewith |
US11769682B2 (en) | 2017-08-09 | 2023-09-26 | Asm Ip Holding B.V. | Storage apparatus for storing cassettes for substrates and processing apparatus equipped therewith |
US10236177B1 (en) | 2017-08-22 | 2019-03-19 | ASM IP Holding B.V.. | Methods for depositing a doped germanium tin semiconductor and related semiconductor device structures |
USD900036S1 (en) | 2017-08-24 | 2020-10-27 | Asm Ip Holding B.V. | Heater electrical connector and adapter |
US11830730B2 (en) | 2017-08-29 | 2023-11-28 | Asm Ip Holding B.V. | Layer forming method and apparatus |
KR102491945B1 (ko) | 2017-08-30 | 2023-01-26 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 |
US11295980B2 (en) | 2017-08-30 | 2022-04-05 | Asm Ip Holding B.V. | Methods for depositing a molybdenum metal film over a dielectric surface of a substrate by a cyclical deposition process and related semiconductor device structures |
US11056344B2 (en) | 2017-08-30 | 2021-07-06 | Asm Ip Holding B.V. | Layer forming method |
US10607895B2 (en) | 2017-09-18 | 2020-03-31 | Asm Ip Holdings B.V. | Method for forming a semiconductor device structure comprising a gate fill metal |
KR102630301B1 (ko) | 2017-09-21 | 2024-01-29 | 에이에스엠 아이피 홀딩 비.브이. | 침투성 재료의 순차 침투 합성 방법 처리 및 이를 이용하여 형성된 구조물 및 장치 |
US10844484B2 (en) | 2017-09-22 | 2020-11-24 | Asm Ip Holding B.V. | Apparatus for dispensing a vapor phase reactant to a reaction chamber and related methods |
US10658205B2 (en) | 2017-09-28 | 2020-05-19 | Asm Ip Holdings B.V. | Chemical dispensing apparatus and methods for dispensing a chemical to a reaction chamber |
US10403504B2 (en) | 2017-10-05 | 2019-09-03 | Asm Ip Holding B.V. | Method for selectively depositing a metallic film on a substrate |
US10319588B2 (en) | 2017-10-10 | 2019-06-11 | Asm Ip Holding B.V. | Method for depositing a metal chalcogenide on a substrate by cyclical deposition |
US10923344B2 (en) | 2017-10-30 | 2021-02-16 | Asm Ip Holding B.V. | Methods for forming a semiconductor structure and related semiconductor structures |
JP7176527B2 (ja) * | 2017-10-31 | 2022-11-22 | 信越化学工業株式会社 | オルガノポリシロキサン組成物、並びに有機ケイ素化合物及びその製造方法 |
KR102443047B1 (ko) | 2017-11-16 | 2022-09-14 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 방법 및 그에 의해 제조된 장치 |
US10910262B2 (en) | 2017-11-16 | 2021-02-02 | Asm Ip Holding B.V. | Method of selectively depositing a capping layer structure on a semiconductor device structure |
US11022879B2 (en) | 2017-11-24 | 2021-06-01 | Asm Ip Holding B.V. | Method of forming an enhanced unexposed photoresist layer |
US11639811B2 (en) | 2017-11-27 | 2023-05-02 | Asm Ip Holding B.V. | Apparatus including a clean mini environment |
CN111316417B (zh) | 2017-11-27 | 2023-12-22 | 阿斯莫Ip控股公司 | 与批式炉偕同使用的用于储存晶圆匣的储存装置 |
US10290508B1 (en) | 2017-12-05 | 2019-05-14 | Asm Ip Holding B.V. | Method for forming vertical spacers for spacer-defined patterning |
US10872771B2 (en) | 2018-01-16 | 2020-12-22 | Asm Ip Holding B. V. | Method for depositing a material film on a substrate within a reaction chamber by a cyclical deposition process and related device structures |
CN111630203A (zh) | 2018-01-19 | 2020-09-04 | Asm Ip私人控股有限公司 | 通过等离子体辅助沉积来沉积间隙填充层的方法 |
TW202325889A (zh) | 2018-01-19 | 2023-07-01 | 荷蘭商Asm 智慧財產控股公司 | 沈積方法 |
USD903477S1 (en) | 2018-01-24 | 2020-12-01 | Asm Ip Holdings B.V. | Metal clamp |
US11018047B2 (en) | 2018-01-25 | 2021-05-25 | Asm Ip Holding B.V. | Hybrid lift pin |
USD880437S1 (en) | 2018-02-01 | 2020-04-07 | Asm Ip Holding B.V. | Gas supply plate for semiconductor manufacturing apparatus |
US10535516B2 (en) | 2018-02-01 | 2020-01-14 | Asm Ip Holdings B.V. | Method for depositing a semiconductor structure on a surface of a substrate and related semiconductor structures |
US11081345B2 (en) | 2018-02-06 | 2021-08-03 | Asm Ip Holding B.V. | Method of post-deposition treatment for silicon oxide film |
US10896820B2 (en) | 2018-02-14 | 2021-01-19 | Asm Ip Holding B.V. | Method for depositing a ruthenium-containing film on a substrate by a cyclical deposition process |
CN116732497A (zh) | 2018-02-14 | 2023-09-12 | Asm Ip私人控股有限公司 | 通过循环沉积工艺在衬底上沉积含钌膜的方法 |
US10731249B2 (en) | 2018-02-15 | 2020-08-04 | Asm Ip Holding B.V. | Method of forming a transition metal containing film on a substrate by a cyclical deposition process, a method for supplying a transition metal halide compound to a reaction chamber, and related vapor deposition apparatus |
US10658181B2 (en) | 2018-02-20 | 2020-05-19 | Asm Ip Holding B.V. | Method of spacer-defined direct patterning in semiconductor fabrication |
KR102636427B1 (ko) | 2018-02-20 | 2024-02-13 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 방법 및 장치 |
US10975470B2 (en) | 2018-02-23 | 2021-04-13 | Asm Ip Holding B.V. | Apparatus for detecting or monitoring for a chemical precursor in a high temperature environment |
US11473195B2 (en) | 2018-03-01 | 2022-10-18 | Asm Ip Holding B.V. | Semiconductor processing apparatus and a method for processing a substrate |
US11629406B2 (en) | 2018-03-09 | 2023-04-18 | Asm Ip Holding B.V. | Semiconductor processing apparatus comprising one or more pyrometers for measuring a temperature of a substrate during transfer of the substrate |
US11114283B2 (en) | 2018-03-16 | 2021-09-07 | Asm Ip Holding B.V. | Reactor, system including the reactor, and methods of manufacturing and using same |
KR102646467B1 (ko) | 2018-03-27 | 2024-03-11 | 에이에스엠 아이피 홀딩 비.브이. | 기판 상에 전극을 형성하는 방법 및 전극을 포함하는 반도체 소자 구조 |
US11230766B2 (en) | 2018-03-29 | 2022-01-25 | Asm Ip Holding B.V. | Substrate processing apparatus and method |
US10510536B2 (en) | 2018-03-29 | 2019-12-17 | Asm Ip Holding B.V. | Method of depositing a co-doped polysilicon film on a surface of a substrate within a reaction chamber |
US11088002B2 (en) | 2018-03-29 | 2021-08-10 | Asm Ip Holding B.V. | Substrate rack and a substrate processing system and method |
KR102501472B1 (ko) | 2018-03-30 | 2023-02-20 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 방법 |
TWI811348B (zh) | 2018-05-08 | 2023-08-11 | 荷蘭商Asm 智慧財產控股公司 | 藉由循環沉積製程於基板上沉積氧化物膜之方法及相關裝置結構 |
TW202349473A (zh) | 2018-05-11 | 2023-12-16 | 荷蘭商Asm Ip私人控股有限公司 | 用於基板上形成摻雜金屬碳化物薄膜之方法及相關半導體元件結構 |
KR102596988B1 (ko) | 2018-05-28 | 2023-10-31 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 방법 및 그에 의해 제조된 장치 |
TW202013553A (zh) | 2018-06-04 | 2020-04-01 | 荷蘭商Asm 智慧財產控股公司 | 水氣降低的晶圓處置腔室 |
US11718913B2 (en) | 2018-06-04 | 2023-08-08 | Asm Ip Holding B.V. | Gas distribution system and reactor system including same |
US11286562B2 (en) | 2018-06-08 | 2022-03-29 | Asm Ip Holding B.V. | Gas-phase chemical reactor and method of using same |
KR102568797B1 (ko) | 2018-06-21 | 2023-08-21 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 시스템 |
US10797133B2 (en) | 2018-06-21 | 2020-10-06 | Asm Ip Holding B.V. | Method for depositing a phosphorus doped silicon arsenide film and related semiconductor device structures |
KR20210027265A (ko) | 2018-06-27 | 2021-03-10 | 에이에스엠 아이피 홀딩 비.브이. | 금속 함유 재료를 형성하기 위한 주기적 증착 방법 및 금속 함유 재료를 포함하는 막 및 구조체 |
WO2020002995A1 (en) | 2018-06-27 | 2020-01-02 | Asm Ip Holding B.V. | Cyclic deposition methods for forming metal-containing material and films and structures including the metal-containing material |
US10612136B2 (en) | 2018-06-29 | 2020-04-07 | ASM IP Holding, B.V. | Temperature-controlled flange and reactor system including same |
KR20200002519A (ko) | 2018-06-29 | 2020-01-08 | 에이에스엠 아이피 홀딩 비.브이. | 박막 증착 방법 및 반도체 장치의 제조 방법 |
US10388513B1 (en) | 2018-07-03 | 2019-08-20 | Asm Ip Holding B.V. | Method for depositing silicon-free carbon-containing film as gap-fill layer by pulse plasma-assisted deposition |
US10755922B2 (en) | 2018-07-03 | 2020-08-25 | Asm Ip Holding B.V. | Method for depositing silicon-free carbon-containing film as gap-fill layer by pulse plasma-assisted deposition |
US10767789B2 (en) | 2018-07-16 | 2020-09-08 | Asm Ip Holding B.V. | Diaphragm valves, valve components, and methods for forming valve components |
US10483099B1 (en) | 2018-07-26 | 2019-11-19 | Asm Ip Holding B.V. | Method for forming thermally stable organosilicon polymer film |
US11053591B2 (en) | 2018-08-06 | 2021-07-06 | Asm Ip Holding B.V. | Multi-port gas injection system and reactor system including same |
US10883175B2 (en) | 2018-08-09 | 2021-01-05 | Asm Ip Holding B.V. | Vertical furnace for processing substrates and a liner for use therein |
US10829852B2 (en) | 2018-08-16 | 2020-11-10 | Asm Ip Holding B.V. | Gas distribution device for a wafer processing apparatus |
US11430674B2 (en) | 2018-08-22 | 2022-08-30 | Asm Ip Holding B.V. | Sensor array, apparatus for dispensing a vapor phase reactant to a reaction chamber and related methods |
KR20200030162A (ko) | 2018-09-11 | 2020-03-20 | 에이에스엠 아이피 홀딩 비.브이. | 박막 증착 방법 |
US11024523B2 (en) | 2018-09-11 | 2021-06-01 | Asm Ip Holding B.V. | Substrate processing apparatus and method |
US11049751B2 (en) | 2018-09-14 | 2021-06-29 | Asm Ip Holding B.V. | Cassette supply system to store and handle cassettes and processing apparatus equipped therewith |
CN110970344A (zh) | 2018-10-01 | 2020-04-07 | Asm Ip控股有限公司 | 衬底保持设备、包含所述设备的系统及其使用方法 |
US11232963B2 (en) | 2018-10-03 | 2022-01-25 | Asm Ip Holding B.V. | Substrate processing apparatus and method |
KR102592699B1 (ko) | 2018-10-08 | 2023-10-23 | 에이에스엠 아이피 홀딩 비.브이. | 기판 지지 유닛 및 이를 포함하는 박막 증착 장치와 기판 처리 장치 |
US10847365B2 (en) | 2018-10-11 | 2020-11-24 | Asm Ip Holding B.V. | Method of forming conformal silicon carbide film by cyclic CVD |
US10811256B2 (en) | 2018-10-16 | 2020-10-20 | Asm Ip Holding B.V. | Method for etching a carbon-containing feature |
KR102605121B1 (ko) | 2018-10-19 | 2023-11-23 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 및 기판 처리 방법 |
KR102546322B1 (ko) | 2018-10-19 | 2023-06-21 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 및 기판 처리 방법 |
USD948463S1 (en) | 2018-10-24 | 2022-04-12 | Asm Ip Holding B.V. | Susceptor for semiconductor substrate supporting apparatus |
US10381219B1 (en) | 2018-10-25 | 2019-08-13 | Asm Ip Holding B.V. | Methods for forming a silicon nitride film |
US11087997B2 (en) | 2018-10-31 | 2021-08-10 | Asm Ip Holding B.V. | Substrate processing apparatus for processing substrates |
KR20200051105A (ko) | 2018-11-02 | 2020-05-13 | 에이에스엠 아이피 홀딩 비.브이. | 기판 지지 유닛 및 이를 포함하는 기판 처리 장치 |
US11572620B2 (en) | 2018-11-06 | 2023-02-07 | Asm Ip Holding B.V. | Methods for selectively depositing an amorphous silicon film on a substrate |
US11031242B2 (en) | 2018-11-07 | 2021-06-08 | Asm Ip Holding B.V. | Methods for depositing a boron doped silicon germanium film |
US10818758B2 (en) | 2018-11-16 | 2020-10-27 | Asm Ip Holding B.V. | Methods for forming a metal silicate film on a substrate in a reaction chamber and related semiconductor device structures |
US10847366B2 (en) | 2018-11-16 | 2020-11-24 | Asm Ip Holding B.V. | Methods for depositing a transition metal chalcogenide film on a substrate by a cyclical deposition process |
US10559458B1 (en) | 2018-11-26 | 2020-02-11 | Asm Ip Holding B.V. | Method of forming oxynitride film |
US11217444B2 (en) | 2018-11-30 | 2022-01-04 | Asm Ip Holding B.V. | Method for forming an ultraviolet radiation responsive metal oxide-containing film |
KR102636428B1 (ko) | 2018-12-04 | 2024-02-13 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치를 세정하는 방법 |
US11158513B2 (en) | 2018-12-13 | 2021-10-26 | Asm Ip Holding B.V. | Methods for forming a rhenium-containing film on a substrate by a cyclical deposition process and related semiconductor device structures |
TW202037745A (zh) | 2018-12-14 | 2020-10-16 | 荷蘭商Asm Ip私人控股有限公司 | 形成裝置結構之方法、其所形成之結構及施行其之系統 |
TWI819180B (zh) | 2019-01-17 | 2023-10-21 | 荷蘭商Asm 智慧財產控股公司 | 藉由循環沈積製程於基板上形成含過渡金屬膜之方法 |
KR20200091543A (ko) | 2019-01-22 | 2020-07-31 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 |
CN111524788B (zh) | 2019-02-01 | 2023-11-24 | Asm Ip私人控股有限公司 | 氧化硅的拓扑选择性膜形成的方法 |
KR102638425B1 (ko) | 2019-02-20 | 2024-02-21 | 에이에스엠 아이피 홀딩 비.브이. | 기판 표면 내에 형성된 오목부를 충진하기 위한 방법 및 장치 |
KR20200102357A (ko) | 2019-02-20 | 2020-08-31 | 에이에스엠 아이피 홀딩 비.브이. | 3-d nand 응용의 플러그 충진체 증착용 장치 및 방법 |
KR102626263B1 (ko) | 2019-02-20 | 2024-01-16 | 에이에스엠 아이피 홀딩 비.브이. | 처리 단계를 포함하는 주기적 증착 방법 및 이를 위한 장치 |
TW202104632A (zh) | 2019-02-20 | 2021-02-01 | 荷蘭商Asm Ip私人控股有限公司 | 用來填充形成於基材表面內之凹部的循環沉積方法及設備 |
TW202100794A (zh) | 2019-02-22 | 2021-01-01 | 荷蘭商Asm Ip私人控股有限公司 | 基材處理設備及處理基材之方法 |
US11742198B2 (en) | 2019-03-08 | 2023-08-29 | Asm Ip Holding B.V. | Structure including SiOCN layer and method of forming same |
KR20200108242A (ko) | 2019-03-08 | 2020-09-17 | 에이에스엠 아이피 홀딩 비.브이. | 실리콘 질화물 층을 선택적으로 증착하는 방법, 및 선택적으로 증착된 실리콘 질화물 층을 포함하는 구조체 |
KR20200108243A (ko) | 2019-03-08 | 2020-09-17 | 에이에스엠 아이피 홀딩 비.브이. | SiOC 층을 포함한 구조체 및 이의 형성 방법 |
KR20200116033A (ko) | 2019-03-28 | 2020-10-08 | 에이에스엠 아이피 홀딩 비.브이. | 도어 개방기 및 이를 구비한 기판 처리 장치 |
KR20200116855A (ko) | 2019-04-01 | 2020-10-13 | 에이에스엠 아이피 홀딩 비.브이. | 반도체 소자를 제조하는 방법 |
KR20200123380A (ko) | 2019-04-19 | 2020-10-29 | 에이에스엠 아이피 홀딩 비.브이. | 층 형성 방법 및 장치 |
KR20200125453A (ko) | 2019-04-24 | 2020-11-04 | 에이에스엠 아이피 홀딩 비.브이. | 기상 반응기 시스템 및 이를 사용하는 방법 |
KR20200130121A (ko) | 2019-05-07 | 2020-11-18 | 에이에스엠 아이피 홀딩 비.브이. | 딥 튜브가 있는 화학물질 공급원 용기 |
KR20200130118A (ko) | 2019-05-07 | 2020-11-18 | 에이에스엠 아이피 홀딩 비.브이. | 비정질 탄소 중합체 막을 개질하는 방법 |
KR20200130652A (ko) | 2019-05-10 | 2020-11-19 | 에이에스엠 아이피 홀딩 비.브이. | 표면 상에 재료를 증착하는 방법 및 본 방법에 따라 형성된 구조 |
JP2020188255A (ja) | 2019-05-16 | 2020-11-19 | エーエスエム アイピー ホールディング ビー.ブイ. | ウェハボートハンドリング装置、縦型バッチ炉および方法 |
USD975665S1 (en) | 2019-05-17 | 2023-01-17 | Asm Ip Holding B.V. | Susceptor shaft |
USD947913S1 (en) | 2019-05-17 | 2022-04-05 | Asm Ip Holding B.V. | Susceptor shaft |
USD935572S1 (en) | 2019-05-24 | 2021-11-09 | Asm Ip Holding B.V. | Gas channel plate |
USD922229S1 (en) | 2019-06-05 | 2021-06-15 | Asm Ip Holding B.V. | Device for controlling a temperature of a gas supply unit |
KR20200141002A (ko) | 2019-06-06 | 2020-12-17 | 에이에스엠 아이피 홀딩 비.브이. | 배기 가스 분석을 포함한 기상 반응기 시스템을 사용하는 방법 |
KR20200143254A (ko) | 2019-06-11 | 2020-12-23 | 에이에스엠 아이피 홀딩 비.브이. | 개질 가스를 사용하여 전자 구조를 형성하는 방법, 상기 방법을 수행하기 위한 시스템, 및 상기 방법을 사용하여 형성되는 구조 |
USD944946S1 (en) | 2019-06-14 | 2022-03-01 | Asm Ip Holding B.V. | Shower plate |
USD931978S1 (en) | 2019-06-27 | 2021-09-28 | Asm Ip Holding B.V. | Showerhead vacuum transport |
KR20210005515A (ko) | 2019-07-03 | 2021-01-14 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치용 온도 제어 조립체 및 이를 사용하는 방법 |
JP2021015791A (ja) | 2019-07-09 | 2021-02-12 | エーエスエム アイピー ホールディング ビー.ブイ. | 同軸導波管を用いたプラズマ装置、基板処理方法 |
CN112216646A (zh) | 2019-07-10 | 2021-01-12 | Asm Ip私人控股有限公司 | 基板支撑组件及包括其的基板处理装置 |
KR20210010307A (ko) | 2019-07-16 | 2021-01-27 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 |
KR20210010816A (ko) | 2019-07-17 | 2021-01-28 | 에이에스엠 아이피 홀딩 비.브이. | 라디칼 보조 점화 플라즈마 시스템 및 방법 |
KR20210010820A (ko) | 2019-07-17 | 2021-01-28 | 에이에스엠 아이피 홀딩 비.브이. | 실리콘 게르마늄 구조를 형성하는 방법 |
US11643724B2 (en) | 2019-07-18 | 2023-05-09 | Asm Ip Holding B.V. | Method of forming structures using a neutral beam |
TW202121506A (zh) | 2019-07-19 | 2021-06-01 | 荷蘭商Asm Ip私人控股有限公司 | 形成形貌受控的非晶碳聚合物膜之方法 |
CN112309843A (zh) | 2019-07-29 | 2021-02-02 | Asm Ip私人控股有限公司 | 实现高掺杂剂掺入的选择性沉积方法 |
CN112309899A (zh) | 2019-07-30 | 2021-02-02 | Asm Ip私人控股有限公司 | 基板处理设备 |
CN112309900A (zh) | 2019-07-30 | 2021-02-02 | Asm Ip私人控股有限公司 | 基板处理设备 |
US11587814B2 (en) | 2019-07-31 | 2023-02-21 | Asm Ip Holding B.V. | Vertical batch furnace assembly |
US11587815B2 (en) | 2019-07-31 | 2023-02-21 | Asm Ip Holding B.V. | Vertical batch furnace assembly |
US11227782B2 (en) | 2019-07-31 | 2022-01-18 | Asm Ip Holding B.V. | Vertical batch furnace assembly |
KR20210018759A (ko) | 2019-08-05 | 2021-02-18 | 에이에스엠 아이피 홀딩 비.브이. | 화학물질 공급원 용기를 위한 액체 레벨 센서 |
USD965524S1 (en) | 2019-08-19 | 2022-10-04 | Asm Ip Holding B.V. | Susceptor support |
USD965044S1 (en) | 2019-08-19 | 2022-09-27 | Asm Ip Holding B.V. | Susceptor shaft |
JP2021031769A (ja) | 2019-08-21 | 2021-03-01 | エーエスエム アイピー ホールディング ビー.ブイ. | 成膜原料混合ガス生成装置及び成膜装置 |
CN110590829A (zh) * | 2019-08-21 | 2019-12-20 | 山东大学 | 一种利用Piers-Rubinsztajn反应制备丙烯酸硅基酯的方法 |
USD949319S1 (en) | 2019-08-22 | 2022-04-19 | Asm Ip Holding B.V. | Exhaust duct |
USD930782S1 (en) | 2019-08-22 | 2021-09-14 | Asm Ip Holding B.V. | Gas distributor |
USD979506S1 (en) | 2019-08-22 | 2023-02-28 | Asm Ip Holding B.V. | Insulator |
KR20210024423A (ko) | 2019-08-22 | 2021-03-05 | 에이에스엠 아이피 홀딩 비.브이. | 홀을 구비한 구조체를 형성하기 위한 방법 |
USD940837S1 (en) | 2019-08-22 | 2022-01-11 | Asm Ip Holding B.V. | Electrode |
US11286558B2 (en) | 2019-08-23 | 2022-03-29 | Asm Ip Holding B.V. | Methods for depositing a molybdenum nitride film on a surface of a substrate by a cyclical deposition process and related semiconductor device structures including a molybdenum nitride film |
KR20210024420A (ko) | 2019-08-23 | 2021-03-05 | 에이에스엠 아이피 홀딩 비.브이. | 비스(디에틸아미노)실란을 사용하여 peald에 의해 개선된 품질을 갖는 실리콘 산화물 막을 증착하기 위한 방법 |
KR20210029090A (ko) | 2019-09-04 | 2021-03-15 | 에이에스엠 아이피 홀딩 비.브이. | 희생 캡핑 층을 이용한 선택적 증착 방법 |
KR20210029663A (ko) | 2019-09-05 | 2021-03-16 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 |
US11562901B2 (en) | 2019-09-25 | 2023-01-24 | Asm Ip Holding B.V. | Substrate processing method |
CN112593212B (zh) | 2019-10-02 | 2023-12-22 | Asm Ip私人控股有限公司 | 通过循环等离子体增强沉积工艺形成拓扑选择性氧化硅膜的方法 |
TW202129060A (zh) | 2019-10-08 | 2021-08-01 | 荷蘭商Asm Ip控股公司 | 基板處理裝置、及基板處理方法 |
TW202115273A (zh) | 2019-10-10 | 2021-04-16 | 荷蘭商Asm Ip私人控股有限公司 | 形成光阻底層之方法及包括光阻底層之結構 |
KR20210045930A (ko) | 2019-10-16 | 2021-04-27 | 에이에스엠 아이피 홀딩 비.브이. | 실리콘 산화물의 토폴로지-선택적 막의 형성 방법 |
US11637014B2 (en) | 2019-10-17 | 2023-04-25 | Asm Ip Holding B.V. | Methods for selective deposition of doped semiconductor material |
KR20210047808A (ko) | 2019-10-21 | 2021-04-30 | 에이에스엠 아이피 홀딩 비.브이. | 막을 선택적으로 에칭하기 위한 장치 및 방법 |
US11646205B2 (en) | 2019-10-29 | 2023-05-09 | Asm Ip Holding B.V. | Methods of selectively forming n-type doped material on a surface, systems for selectively forming n-type doped material, and structures formed using same |
KR20210054983A (ko) | 2019-11-05 | 2021-05-14 | 에이에스엠 아이피 홀딩 비.브이. | 도핑된 반도체 층을 갖는 구조체 및 이를 형성하기 위한 방법 및 시스템 |
JP7298446B2 (ja) | 2019-11-07 | 2023-06-27 | 信越化学工業株式会社 | アクリロイルオキシ基またはメタクリロイルオキシ基を有する有機ケイ素化合物の製造方法 |
US11501968B2 (en) | 2019-11-15 | 2022-11-15 | Asm Ip Holding B.V. | Method for providing a semiconductor device with silicon filled gaps |
KR20210062561A (ko) | 2019-11-20 | 2021-05-31 | 에이에스엠 아이피 홀딩 비.브이. | 기판의 표면 상에 탄소 함유 물질을 증착하는 방법, 상기 방법을 사용하여 형성된 구조물, 및 상기 구조물을 형성하기 위한 시스템 |
US11450529B2 (en) | 2019-11-26 | 2022-09-20 | Asm Ip Holding B.V. | Methods for selectively forming a target film on a substrate comprising a first dielectric surface and a second metallic surface |
CN112951697A (zh) | 2019-11-26 | 2021-06-11 | Asm Ip私人控股有限公司 | 基板处理设备 |
CN112885693A (zh) | 2019-11-29 | 2021-06-01 | Asm Ip私人控股有限公司 | 基板处理设备 |
CN112885692A (zh) | 2019-11-29 | 2021-06-01 | Asm Ip私人控股有限公司 | 基板处理设备 |
JP2021090042A (ja) | 2019-12-02 | 2021-06-10 | エーエスエム アイピー ホールディング ビー.ブイ. | 基板処理装置、基板処理方法 |
KR20210070898A (ko) | 2019-12-04 | 2021-06-15 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 |
TW202125596A (zh) | 2019-12-17 | 2021-07-01 | 荷蘭商Asm Ip私人控股有限公司 | 形成氮化釩層之方法以及包括該氮化釩層之結構 |
US11527403B2 (en) | 2019-12-19 | 2022-12-13 | Asm Ip Holding B.V. | Methods for filling a gap feature on a substrate surface and related semiconductor structures |
KR20210095050A (ko) | 2020-01-20 | 2021-07-30 | 에이에스엠 아이피 홀딩 비.브이. | 박막 형성 방법 및 박막 표면 개질 방법 |
TW202130846A (zh) | 2020-02-03 | 2021-08-16 | 荷蘭商Asm Ip私人控股有限公司 | 形成包括釩或銦層的結構之方法 |
TW202146882A (zh) | 2020-02-04 | 2021-12-16 | 荷蘭商Asm Ip私人控股有限公司 | 驗證一物品之方法、用於驗證一物品之設備、及用於驗證一反應室之系統 |
US11776846B2 (en) | 2020-02-07 | 2023-10-03 | Asm Ip Holding B.V. | Methods for depositing gap filling fluids and related systems and devices |
TW202146715A (zh) | 2020-02-17 | 2021-12-16 | 荷蘭商Asm Ip私人控股有限公司 | 用於生長磷摻雜矽層之方法及其系統 |
US11876356B2 (en) | 2020-03-11 | 2024-01-16 | Asm Ip Holding B.V. | Lockout tagout assembly and system and method of using same |
KR20210116240A (ko) | 2020-03-11 | 2021-09-27 | 에이에스엠 아이피 홀딩 비.브이. | 조절성 접합부를 갖는 기판 핸들링 장치 |
KR20210124042A (ko) | 2020-04-02 | 2021-10-14 | 에이에스엠 아이피 홀딩 비.브이. | 박막 형성 방법 |
TW202146689A (zh) | 2020-04-03 | 2021-12-16 | 荷蘭商Asm Ip控股公司 | 阻障層形成方法及半導體裝置的製造方法 |
TW202145344A (zh) | 2020-04-08 | 2021-12-01 | 荷蘭商Asm Ip私人控股有限公司 | 用於選擇性蝕刻氧化矽膜之設備及方法 |
US11821078B2 (en) | 2020-04-15 | 2023-11-21 | Asm Ip Holding B.V. | Method for forming precoat film and method for forming silicon-containing film |
KR20210132605A (ko) | 2020-04-24 | 2021-11-04 | 에이에스엠 아이피 홀딩 비.브이. | 냉각 가스 공급부를 포함한 수직형 배치 퍼니스 어셈블리 |
KR20210132576A (ko) | 2020-04-24 | 2021-11-04 | 에이에스엠 아이피 홀딩 비.브이. | 바나듐 나이트라이드 함유 층을 형성하는 방법 및 이를 포함하는 구조 |
KR20210132600A (ko) | 2020-04-24 | 2021-11-04 | 에이에스엠 아이피 홀딩 비.브이. | 바나듐, 질소 및 추가 원소를 포함한 층을 증착하기 위한 방법 및 시스템 |
KR20210134869A (ko) | 2020-05-01 | 2021-11-11 | 에이에스엠 아이피 홀딩 비.브이. | Foup 핸들러를 이용한 foup의 빠른 교환 |
KR20210141379A (ko) | 2020-05-13 | 2021-11-23 | 에이에스엠 아이피 홀딩 비.브이. | 반응기 시스템용 레이저 정렬 고정구 |
KR20210143653A (ko) | 2020-05-19 | 2021-11-29 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치 |
KR20210145078A (ko) | 2020-05-21 | 2021-12-01 | 에이에스엠 아이피 홀딩 비.브이. | 다수의 탄소 층을 포함한 구조체 및 이를 형성하고 사용하는 방법 |
TW202201602A (zh) | 2020-05-29 | 2022-01-01 | 荷蘭商Asm Ip私人控股有限公司 | 基板處理方法 |
TW202218133A (zh) | 2020-06-24 | 2022-05-01 | 荷蘭商Asm Ip私人控股有限公司 | 形成含矽層之方法 |
TW202217953A (zh) | 2020-06-30 | 2022-05-01 | 荷蘭商Asm Ip私人控股有限公司 | 基板處理方法 |
KR20220010438A (ko) | 2020-07-17 | 2022-01-25 | 에이에스엠 아이피 홀딩 비.브이. | 포토리소그래피에 사용하기 위한 구조체 및 방법 |
TW202204662A (zh) | 2020-07-20 | 2022-02-01 | 荷蘭商Asm Ip私人控股有限公司 | 用於沉積鉬層之方法及系統 |
KR20220027026A (ko) | 2020-08-26 | 2022-03-07 | 에이에스엠 아이피 홀딩 비.브이. | 금속 실리콘 산화물 및 금속 실리콘 산질화물 층을 형성하기 위한 방법 및 시스템 |
USD990534S1 (en) | 2020-09-11 | 2023-06-27 | Asm Ip Holding B.V. | Weighted lift pin |
USD1012873S1 (en) | 2020-09-24 | 2024-01-30 | Asm Ip Holding B.V. | Electrode for semiconductor processing apparatus |
WO2022066342A1 (en) | 2020-09-24 | 2022-03-31 | Dow Silicones Corporation | Methods for the preparation and use of silyl ester compounds |
TW202229613A (zh) | 2020-10-14 | 2022-08-01 | 荷蘭商Asm Ip私人控股有限公司 | 於階梯式結構上沉積材料的方法 |
TW202217037A (zh) | 2020-10-22 | 2022-05-01 | 荷蘭商Asm Ip私人控股有限公司 | 沉積釩金屬的方法、結構、裝置及沉積總成 |
TW202223136A (zh) | 2020-10-28 | 2022-06-16 | 荷蘭商Asm Ip私人控股有限公司 | 用於在基板上形成層之方法、及半導體處理系統 |
KR20220076343A (ko) | 2020-11-30 | 2022-06-08 | 에이에스엠 아이피 홀딩 비.브이. | 기판 처리 장치의 반응 챔버 내에 배열되도록 구성된 인젝터 |
CN114639631A (zh) | 2020-12-16 | 2022-06-17 | Asm Ip私人控股有限公司 | 跳动和摆动测量固定装置 |
TW202231903A (zh) | 2020-12-22 | 2022-08-16 | 荷蘭商Asm Ip私人控股有限公司 | 過渡金屬沉積方法、過渡金屬層、用於沉積過渡金屬於基板上的沉積總成 |
USD980813S1 (en) | 2021-05-11 | 2023-03-14 | Asm Ip Holding B.V. | Gas flow control plate for substrate processing apparatus |
USD981973S1 (en) | 2021-05-11 | 2023-03-28 | Asm Ip Holding B.V. | Reactor wall for substrate processing apparatus |
USD980814S1 (en) | 2021-05-11 | 2023-03-14 | Asm Ip Holding B.V. | Gas distributor for substrate processing apparatus |
USD990441S1 (en) | 2021-09-07 | 2023-06-27 | Asm Ip Holding B.V. | Gas flow control plate |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0643414B2 (ja) | 1985-10-17 | 1994-06-08 | 日東化学工業株式会社 | 2,2ジメチルδバレロラクトンの製造方法 |
EP0219117B1 (en) | 1985-10-17 | 1990-08-16 | Nitto Chemical Industry Co., Ltd. | A method for producing alpha,alpha-dimethyl-delta-valerolactone |
SU1397428A1 (ru) | 1986-08-11 | 1988-05-23 | Львовский политехнический институт им.Ленинского комсомола | Способ получени 2,2-диметилпентен-4-овой кислоты |
US5534562A (en) | 1995-04-07 | 1996-07-09 | Ultradent Products, Inc. | Compositions and methods for priming and sealing dental and biological substrates |
JP2978435B2 (ja) | 1996-01-24 | 1999-11-15 | チッソ株式会社 | アクリロキシプロピルシランの製造方法 |
JPH11193291A (ja) | 1997-12-26 | 1999-07-21 | Chisso Corp | エステル基含有シロキサン化合物、及びその製造方法 |
JP3864648B2 (ja) | 1999-11-30 | 2007-01-10 | 東亞合成株式会社 | 1,3−ビス(カルボキシアルキル)テトラアルキルジシロキサンの製造方法 |
-
2003
- 2003-09-25 JP JP2003333014A patent/JP4524554B2/ja not_active Expired - Fee Related
-
2004
- 2004-09-23 US US10/947,129 patent/US7307178B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP2005097173A (ja) | 2005-04-14 |
US20050070729A1 (en) | 2005-03-31 |
US7307178B2 (en) | 2007-12-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4524554B2 (ja) | γ,δ−不飽和カルボン酸及びそのシリルエステルの製造方法、カルボキシル基を有する有機ケイ素化合物及びその製造方法 | |
EP2787000B1 (en) | Hydrosilylation method, method for producing oranosilicon compound, and organosilicon compound | |
JP3651572B2 (ja) | 部分付加環状オルガノハイドロジェンシロキサンの製造方法 | |
JP3108427B2 (ja) | カルビノール基含有オルガノポリシロキサンの製造方法 | |
JP5664192B2 (ja) | 有機ケイ素化合物の製造方法 | |
JP3556642B2 (ja) | 第二級アミノイソブチルアルコキシシラン類の調製 | |
JP4296416B2 (ja) | シリルケテンアセタール及びジシリルケテンアセタールの製造方法 | |
JP5664191B2 (ja) | 有機ケイ素化合物の製造方法 | |
JP3865082B2 (ja) | シロキサン化合物およびその製造方法 | |
JP5062231B2 (ja) | アルコール性水酸基を有する有機ケイ素樹脂及びその製造方法 | |
JP3915875B2 (ja) | N−置換−3−シリルプロピルアミン類及びその誘導体の製造方法 | |
JP3812647B2 (ja) | オルガノオキシ基またはヒドロキシル基を有するシロキサンの製造方法 | |
JP4453827B2 (ja) | シロキサン結合を有するオルガノキシシラン化合物及びその製造方法 | |
WO2007007597A1 (ja) | 新規な有機ケイ素化合物及びその製造方法 | |
EP1471069B1 (en) | Preparation of silyl ketene acetals and disilyl ketene acetals | |
JPH11193291A (ja) | エステル基含有シロキサン化合物、及びその製造方法 | |
US20120165565A1 (en) | Synthesis of fluorocarbofunctional alkoxysilanes and chlorosilanes | |
US6136940A (en) | Silacyclobutane compounds, methods of preparing same, and polymers formed therefrom | |
JP4081572B2 (ja) | 水酸基を有する化合物のシリル化方法 | |
JP2002012597A (ja) | 有機ケイ素化合物 | |
JP4172342B2 (ja) | 環状有機ケイ素化合物及びその製造方法 | |
EP1046641A1 (en) | Silacyclobutene compounds | |
JP2001354678A (ja) | 有機ケイ素化合物、およびその製造方法 | |
JP4433563B2 (ja) | 有機ケイ素化合物 | |
JP2004067802A (ja) | オルガノキシ基又はヒドロキシル基を有するシロキサンの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050811 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20090126 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090204 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090402 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090930 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20091126 |
|
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: 20100506 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100519 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130611 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 4524554 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |