DE3025034A1 - Silane und verfahren zu ihrer herstellung - Google Patents
Silane und verfahren zu ihrer herstellungInfo
- Publication number
- DE3025034A1 DE3025034A1 DE19803025034 DE3025034A DE3025034A1 DE 3025034 A1 DE3025034 A1 DE 3025034A1 DE 19803025034 DE19803025034 DE 19803025034 DE 3025034 A DE3025034 A DE 3025034A DE 3025034 A1 DE3025034 A1 DE 3025034A1
- Authority
- DE
- Germany
- Prior art keywords
- stands
- carbon atoms
- alkyl
- alkaline earth
- liquid
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 31
- 238000009835 boiling Methods 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 239000012429 reaction media Substances 0.000 claims description 15
- 150000004756 silanes Chemical class 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 150000001340 alkali metals Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 229910000077 silane Inorganic materials 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000011630 iodine Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- QLVKECUOHNDWOI-UHFFFAOYSA-N 2-oxo-1,3,2$l^{5}-diazaphosphonan-2-amine Chemical compound NP1(=O)NCCCCCCN1 QLVKECUOHNDWOI-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-IGMARMGPSA-N Carbon-12 Chemical compound [12C] OKTJSMMVPCPJKN-IGMARMGPSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000010533 azeotropic distillation Methods 0.000 description 12
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- -1 phenoxy, thiophenoxy, pyridyloxy Chemical group 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000011343 solid material Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000012808 vapor phase Substances 0.000 description 5
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 2
- 229940018563 3-aminophenol Drugs 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- FGYPEIBVFQOQKC-UHFFFAOYSA-N 4-(3-trimethoxysilylpropoxy)aniline Chemical compound CO[Si](OC)(OC)CCCOC1=CC=C(N)C=C1 FGYPEIBVFQOQKC-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000004806 hydroxypyridines Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JDESAODINAIGSD-UHFFFAOYSA-N trimethoxy(3-pyridin-3-yloxypropyl)silane Chemical compound CO[Si](OC)(OC)CCCOC1=CC=CN=C1 JDESAODINAIGSD-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- KONYWZRRCDRQQS-UHFFFAOYSA-N (3-chloro-2-methylpropyl)-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CC(C)CCl KONYWZRRCDRQQS-UHFFFAOYSA-N 0.000 description 1
- JKQLQZKMBVUJCI-UHFFFAOYSA-N 1-(3-hydroxyphenyl)pyrrolidine-2,5-dione Chemical compound OC1=CC=CC(N2C(CCC2=O)=O)=C1 JKQLQZKMBVUJCI-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- HUPGCAGBHBJUJC-UHFFFAOYSA-N 3-(3-trimethoxysilylpropoxy)aniline Chemical compound CO[Si](OC)(OC)CCCOC1=CC=CC(N)=C1 HUPGCAGBHBJUJC-UHFFFAOYSA-N 0.000 description 1
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- CQAKEDKOKFHMSM-UHFFFAOYSA-N 3-[3-[dimethoxy(methyl)silyl]propoxy]aniline Chemical compound CO[Si](C)(OC)CCCOC1=CC=CC(N)=C1 CQAKEDKOKFHMSM-UHFFFAOYSA-N 0.000 description 1
- CFWIOOCJVYJEID-UHFFFAOYSA-N 3-amino-2-chlorophenol Chemical class NC1=CC=CC(O)=C1Cl CFWIOOCJVYJEID-UHFFFAOYSA-N 0.000 description 1
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 1
- BKCYLOLTKVUVPA-UHFFFAOYSA-N 4-(3-trimethoxysilylpropoxy)benzaldehyde Chemical compound CO[Si](OC)(OC)CCCOC1=CC=C(C=O)C=C1 BKCYLOLTKVUVPA-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- DOSDTCPDBPRFHQ-UHFFFAOYSA-N dimethyl 5-hydroxybenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(O)=CC(C(=O)OC)=C1 DOSDTCPDBPRFHQ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- YZDXARUSBHCWPP-UHFFFAOYSA-N methyl 4-[3-[dimethoxy(methyl)silyl]propoxy]benzoate Chemical compound COC(=O)C1=CC=C(OCCC[Si](C)(OC)OC)C=C1 YZDXARUSBHCWPP-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- DDESMIQDZAUXOY-UHFFFAOYSA-N n,n-diethyl-3-(3-trimethoxysilylpropoxy)aniline Chemical compound CCN(CC)C1=CC=CC(OCCC[Si](OC)(OC)OC)=C1 DDESMIQDZAUXOY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- VUHPZDVFOAYSLG-UHFFFAOYSA-N trimethoxy(3-phenoxypropyl)silane Chemical compound CO[Si](OC)(OC)CCCOC1=CC=CC=C1 VUHPZDVFOAYSLG-UHFFFAOYSA-N 0.000 description 1
- XWCDBMOCZRPUMN-UHFFFAOYSA-N trimethoxy-[3-(2-prop-1-enylphenoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOC1=CC=CC=C1C=CC XWCDBMOCZRPUMN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6471279A | 1979-08-08 | 1979-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3025034A1 true DE3025034A1 (de) | 1981-02-26 |
Family
ID=22057794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803025034 Ceased DE3025034A1 (de) | 1979-08-08 | 1980-07-02 | Silane und verfahren zu ihrer herstellung |
Country Status (13)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5967660A (ja) * | 1982-10-12 | 1984-04-17 | Toshiba Corp | 封止用エポキシ樹脂組成物及びこれを用いた樹脂封止型半導体装置 |
| WO1986006089A1 (en) * | 1985-04-17 | 1986-10-23 | Dainichi Nihon Densen Kabusikikaisha | Filler composition and process for its production |
| JP2534330B2 (ja) * | 1988-09-12 | 1996-09-11 | 日東電工株式会社 | 半導体装置 |
| DE3935638A1 (de) * | 1989-10-26 | 1991-05-02 | Consortium Elektrochem Ind | Organosilylalkylaromaten |
| JP2939016B2 (ja) * | 1991-08-26 | 1999-08-25 | 信越化学工業株式会社 | ３−（ビニルフェニルオキシ）プロピルシラン化合物の製造方法 |
| JP2792395B2 (ja) * | 1992-12-10 | 1998-09-03 | 信越化学工業株式会社 | エポキシ樹脂用硬化剤及びエポキシ樹脂組成物並びに半導体装置 |
| JP3876944B2 (ja) | 1997-12-24 | 2007-02-07 | 北興化学工業株式会社 | 半導体封止用エポキシ樹脂組成物及び半導体装置 |
| JP4054927B2 (ja) | 1998-06-25 | 2008-03-05 | 北興化学工業株式会社 | 半導体封止用エポキシ樹脂組成物及び半導体装置 |
| JP5245076B2 (ja) * | 2008-09-30 | 2013-07-24 | 大同化学工業株式会社 | 廃液の処理方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1062418A (en) * | 1964-01-27 | 1967-03-22 | Ici Ltd | New nitrogen-containing siloxanes |
| US3355424A (en) * | 1964-07-29 | 1967-11-28 | Dow Corning | Method for the preparation of aminoalkylsiloxane copolymers |
| DE2426991A1 (de) * | 1973-06-07 | 1975-01-02 | Ciba Geigy Ag | Vernetzte siloxangruppenhaltige polymere |
| FR2243022A1 (enrdf_load_stackoverflow) * | 1973-09-10 | 1975-04-04 | Rhone Progil | |
| DE2439088B2 (de) * | 1973-08-17 | 1976-10-28 | Rhone-Progil S.A., Courbevoie, Hautsde-Seine (Frankreich) | Verfahren zur herstellung von aminoaromatisch substituierten silanen und den entsprechenden polymeren |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1054041A (enrdf_load_stackoverflow) * | 1900-01-01 | |||
| US2783262A (en) * | 1954-11-22 | 1957-02-26 | Dow Corning | Halophenoxysiloxanes |
| DE2215629A1 (de) * | 1972-03-30 | 1973-10-04 | Dynamit Nobel Ag | Kernsubstituierte aralkylsilane |
| FR2226407B1 (enrdf_load_stackoverflow) * | 1973-04-17 | 1978-05-26 | Rhone Progil | |
| US4049691A (en) * | 1973-08-17 | 1977-09-20 | Rhone-Progil | Aromatic amino silanes and their polymers |
| CH632765A5 (de) * | 1977-09-09 | 1982-10-29 | Ciba Geigy Ag | Verfahren zur herstellung von siliciummodifizierten phthalsaeurederivaten. |
| GB2019862B (en) * | 1978-04-26 | 1982-05-19 | M & T Chemicals Inc | Phenoxyalkyl-silanes |
| IL59345A0 (en) * | 1979-02-13 | 1980-05-30 | M & T Chemicals Inc | Silicone-containing bis-ether and bis-thioether aromatic amines and their manufacture |
-
1980
- 1980-05-12 ES ES491385A patent/ES8105009A2/es not_active Expired
- 1980-06-12 GB GB8019271A patent/GB2055871B/en not_active Expired
- 1980-06-27 SE SE8004782A patent/SE8004782L/ not_active Application Discontinuation
- 1980-07-02 DE DE19803025034 patent/DE3025034A1/de not_active Ceased
- 1980-07-03 NL NL8003863A patent/NL8003863A/nl not_active Application Discontinuation
- 1980-07-07 JP JP9183280A patent/JPS5645491A/ja active Granted
- 1980-07-09 CA CA000355796A patent/CA1152511A/en not_active Expired
- 1980-07-11 KR KR1019800002772A patent/KR850000912B1/ko not_active Expired
- 1980-07-15 CH CH5436/80A patent/CH661928A5/de not_active IP Right Cessation
- 1980-08-04 FR FR8017158A patent/FR2463148B1/fr not_active Expired
- 1980-08-06 NO NO802356A patent/NO802356L/no unknown
- 1980-08-06 BE BE0/201666A patent/BE884652R/fr not_active IP Right Cessation
- 1980-08-08 IT IT09514/80A patent/IT1153845B/it active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1062418A (en) * | 1964-01-27 | 1967-03-22 | Ici Ltd | New nitrogen-containing siloxanes |
| US3355424A (en) * | 1964-07-29 | 1967-11-28 | Dow Corning | Method for the preparation of aminoalkylsiloxane copolymers |
| DE2426991A1 (de) * | 1973-06-07 | 1975-01-02 | Ciba Geigy Ag | Vernetzte siloxangruppenhaltige polymere |
| DE2439088B2 (de) * | 1973-08-17 | 1976-10-28 | Rhone-Progil S.A., Courbevoie, Hautsde-Seine (Frankreich) | Verfahren zur herstellung von aminoaromatisch substituierten silanen und den entsprechenden polymeren |
| FR2243022A1 (enrdf_load_stackoverflow) * | 1973-09-10 | 1975-04-04 | Rhone Progil |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8009514A0 (it) | 1980-08-08 |
| NL8003863A (nl) | 1981-02-10 |
| JPS5645491A (en) | 1981-04-25 |
| JPS6352629B2 (enrdf_load_stackoverflow) | 1988-10-19 |
| ES491385A0 (es) | 1981-05-16 |
| KR850000912B1 (ko) | 1985-06-27 |
| ES8105009A2 (es) | 1981-05-16 |
| FR2463148B1 (fr) | 1987-08-28 |
| BE884652R (fr) | 1980-12-01 |
| FR2463148A1 (fr) | 1981-02-20 |
| GB2055871B (en) | 1983-10-19 |
| CH661928A5 (de) | 1987-08-31 |
| NO802356L (no) | 1981-02-09 |
| KR830003504A (ko) | 1983-06-21 |
| IT1153845B (it) | 1987-01-21 |
| GB2055871A (en) | 1981-03-11 |
| CA1152511A (en) | 1983-08-23 |
| SE8004782L (sv) | 1981-02-09 |
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