EP2384330A1 - Procédé de production de bis et tris(silyl-organo)amines - Google Patents
Procédé de production de bis et tris(silyl-organo)aminesInfo
- Publication number
- EP2384330A1 EP2384330A1 EP10700566A EP10700566A EP2384330A1 EP 2384330 A1 EP2384330 A1 EP 2384330A1 EP 10700566 A EP10700566 A EP 10700566A EP 10700566 A EP10700566 A EP 10700566A EP 2384330 A1 EP2384330 A1 EP 2384330A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- general formula
- silane
- base
- aminoorganyl
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 150000001412 amines Chemical class 0.000 title description 8
- 239000007983 Tris buffer Substances 0.000 title description 5
- -1 ammonium halide Chemical class 0.000 claims abstract description 52
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 43
- 229910000077 silane Inorganic materials 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 150000004820 halides Chemical class 0.000 claims abstract description 15
- 150000004756 silanes Chemical class 0.000 claims abstract description 15
- 239000006227 byproduct Substances 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 32
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 description 36
- 239000000047 product Substances 0.000 description 27
- 238000004821 distillation Methods 0.000 description 22
- 239000012071 phase Substances 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 15
- 238000005191 phase separation Methods 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229910007991 Si-N Inorganic materials 0.000 description 4
- 229910006294 Si—N Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- HCFPRFJJTHMING-UHFFFAOYSA-N ethane-1,2-diamine;hydron;chloride Chemical compound [Cl-].NCC[NH3+] HCFPRFJJTHMING-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 2
- IWBZCSOSMAHIJG-UHFFFAOYSA-N 3-trimethoxysilyl-n-(trimethoxysilylmethyl)-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C[Si](OC)(OC)OC)CCC[Si](OC)(OC)OC IWBZCSOSMAHIJG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- 229920004482 WACKER® Polymers 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XTOFCKRYGWPHPI-UHFFFAOYSA-N n-(triethoxysilylmethyl)-1-trimethylsilyl-n-(trimethylsilylmethyl)methanamine Chemical compound CCO[Si](OCC)(OCC)CN(C[Si](C)(C)C)C[Si](C)(C)C XTOFCKRYGWPHPI-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical group CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- BZJILDWKZIVTPE-UHFFFAOYSA-N 1-trimethylsilyl-n-(trimethylsilylmethyl)methanamine Chemical compound C[Si](C)(C)CNC[Si](C)(C)C BZJILDWKZIVTPE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- FWRGWYSLZSBKPG-UHFFFAOYSA-N N-(dimethoxymethylsilylmethyl)-N-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCN(C[SiH2]C(OC)OC)C1=CC=CC=C1 FWRGWYSLZSBKPG-UHFFFAOYSA-N 0.000 description 1
- TXAUMPQRSDQWCL-UHFFFAOYSA-N N-(dimethoxymethylsilylmethyl)aniline Chemical compound COC(OC)[SiH2]CNC1=CC=CC=C1 TXAUMPQRSDQWCL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- ZDOBWJOCPDIBRZ-UHFFFAOYSA-N chloromethyl(triethoxy)silane Chemical compound CCO[Si](CCl)(OCC)OCC ZDOBWJOCPDIBRZ-UHFFFAOYSA-N 0.000 description 1
- FPOSCXQHGOVVPD-UHFFFAOYSA-N chloromethyl(trimethoxy)silane Chemical compound CO[Si](CCl)(OC)OC FPOSCXQHGOVVPD-UHFFFAOYSA-N 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 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 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- BRIUVZVCZNEQGX-UHFFFAOYSA-N methylsilylmethanamine Chemical compound NC[SiH2]C BRIUVZVCZNEQGX-UHFFFAOYSA-N 0.000 description 1
- ORTBNRNXWKEDNZ-UHFFFAOYSA-N n-(trimethoxysilylmethyl)-n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCN(C[Si](OC)(OC)OC)C1=CC=CC=C1 ORTBNRNXWKEDNZ-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C07F7/0803—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
-
- 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
Definitions
- the invention relates to a process for the preparation of bis- and tris (silylorgano) amines, by reacting (aminoorganyl) silanes with (haloorganyl) silanes.
- Transition metal catalysts used to prepare preferably bis (silylorganyl) silanes preferably bis (silylorganyl) silanes.
- Transition metal catalysts in the presence of ammonia wherein u.a. Bis (silylorganyl) silanes are formed.
- EP 167887 Bl describes the specific preparation of bis-silylalkylamines starting from cyanoorganosilane and
- Transition metal catalysts are Transition metal catalysts.
- EP 531948 B1 describes the reaction of aminoalkylsilanes on a palladium oxide catalyst, symmetrical bis- and tris-silylalkylamines being prepared. Drastic conditions are necessary (200 0 C / 6h) and are obtained in each case mixtures of mono-, bis- and tris-substitution product.
- EP 709391 Bl describes the hydrosilylation of bisallylaraine with trialkoxysilane to bis-silylorganylamine.
- a disadvantage is in addition to the use of expensive hydrosilylation catalysts, the use of some highly toxic starting materials, which requires a high level of security.
- EP 849271 Bl describes starting from chloroorganosilanes the preparation of the corresponding primary Aminoorganylsilane with ammonia, as by-products and the di- and
- Trisubstitutions occur.
- the reaction requires the use of autoclave and drastic reaction conditions.
- the target products are always obtained in admixture with mono-, di- and trisubstitution product and silylorganyl-substituted amines with different silyl radicals in one molecule are not specifically accessible in this way.
- a disadvantage of this process is also the fact that ammonium halide is formed as a by-product in quantitative amounts and has to be separated off as a solid. Separation of such large quantities of solids is time-consuming and therefore cost-intensive, and also requires production plants which are connected via corresponding equipment, e.g. powerful and therefore expensive centrifuges. However, this is true of many systems - especially in most multi-purpose systems, as is typical for
- US 6452033 A describes the preparation of Aminoethylaminoorganyl-triorganylsilanen by the reaction of the corresponding chlorofunctional organosilanes with ethylenediamine, wherein the above-mentioned phase separation for the separation of the hydrochlorides is used in various ways.
- a disadvantage of this process is the fact that it is limited to silanes which have an ethylenediamine unit.
- chloroorganosilanes e.g. are obtainable by means of photochlorination of alkylsilanes or hydrosilylation of corresponding halogen-substituted olefins to Si-H-containing compounds and are used, for example, as intermediates for the synthesis of a variety of organofunctional silanes.
- the invention relates to a process for preparing silylorganoamines of the general formula (1)
- R ', R' 'an alkoxy radical each having 1-10 C atoms
- Rl, R5 is a hydrocarbon radical having 1-10 C atoms
- R ⁇ is a divalent hydrocarbon radical having 1-10 C atoms, in which the hydrocarbon chain may be interrupted by carbonyl groups, carboxyl groups, oxygen atoms or sulfur atoms
- R ⁇ is a bivalent hydrocarbon radical having 1-10 C atoms, in which the hydrocarbon chain by carbonyl groups, carboxyl groups , Oxygen atoms, sulfur atoms, NH or
- NR ⁇ groups may be interrupted, wherein R ⁇ belongs to the same meaning as R ⁇ , R 5, R 3 is hydrogen, a hydrocarbon radical having 1-10 carbon atoms, or a radical of the general formula R '''3_ o R ⁇ o Si-R ⁇ -, where R6 has the same meaning as R ⁇ and R ⁇ ,
- X is chlorine, bromine or iodine mean
- the reaction comprises the following steps: a) reacting the (haloorganyl) silane of the general formula (3) and (aminoorganyl) silane of the general formula (2) at a temperature from 0 to 250 0 C, wherein in addition to the silylorganoamine of the general formula (1) as a by-product, the ammonium halide of (aminoorganyl) silane of the general formula (2) is formed, b) addition of a base (B), wherein it comes to a complete or partial salification at the (aminoorganyl) silane of the general formula (2) is liberated again and the halide of the base (B) is formed, the halide of the base (B) being liquid at temperatures of at most 200 ° C., and c) separation of the formed liquid halide of the base (B).
- ammonium halide of the (aminoorganyl) silane of the general formula (2) typically precipitates as an insoluble solid which, in step b), re-dissolves after the base (B) has been added, forming a separate liquid phase which is essentially the Halide of the base (B) and then separated in step c).
- the (aminoorganyl) silane of the general formula (2) is preferably present in excess, ie. in molar ratios of 1.1 to 1 to 100 to 1, preferably from 1.5 to 1 to 50 to 1, more preferably from 2 to 1 to 20 to 1, in particular from 3 to 1 to 10 to 1 used.
- the base (B) is preferably in molar ratios of 0.5 to 1 to 10 to 1, preferably from 0.7 to 1 to 5 to 1, particularly preferably from 0.8 to 1 to 2 to 1, in particular from 0.9 to 1 to 1.0 to 1 used.
- the hydrocarbon radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 may be saturated or unsaturated, branched or unbranched, substituted or unsubstituted.
- the hydrocarbon radicals R 1, R 3 , R 5, R 6 may be alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-n-butyl, isobutyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert. -Pentylrest; Hexyl radicals, such as the n-hexyl radical; Heptyl radicals, such as the n-heptyl radical; Octyl radicals, such as the n-octyl radical and iso-octyl radicals, such as the 2,2,4-
- Nonyl radicals such as the n-nonyl radical; Decyl radicals, such as the n-decyl radical; Dodecyl radicals, such as the n-dodecyl radical; Octadecyl radicals, such as the n-octadecyl radical; Cycloalkyl radicals such as the cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl radicals; Alkenyl radicals such as the vinyl, 1-propenyl, 2-propenyl and the 10-undecenyl radical; Aryl radicals, such as the phenyl, naphthyl, anthryl and phenanthryl radicals; Alkaryl radicals, such as o-, m-, p-tolyl radicals; Xylyl radicals and ethylphenyl radicals; and aralkyl radicals, such as the n-nonyl radical
- the hydrocarbon radicals R ⁇ , R ⁇ , R ⁇ , R6 preferably have 1-6, in particular 1-3 C-atoms.
- R ⁇ , R ⁇ , R *> are a methyl, ethyl, iso and n-propyl, iso and n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl , Phenyl, benzyl or allyl radical.
- the radical R is preferably selected from the preferred radicals from RI, R5, R6 and further from hydrogen, Cylclohexyl- or phenyl or the radical of the formula R '' 'o R 3_ east o si-R' - selected. Particularly preferred is the radical
- radicals R ', R ", R"' preferably have the meaning of
- R ', R ", R'” are independently methoxy, ethoxy, iso and n-propoxy, butoxy, phenoxy, benzyloxy or allyloxy.
- R ', R ", R'" are the same.
- the radicals R 1, R 4 / R 7 are preferably a divalent hydrocarbon radical having 1-6 C atoms, in particular a methylene, ethylene and propylene group, particularly preferably the methylene and propylene groups.
- the radical X is preferably chlorine or bromine, in particular chlorine.
- m, ii / o independently of one another preferably have the value 0, 1 or 2, particularly preferably 0 or 1.
- steps a) and b) can be carried out successively or simultaneously. Also conceivable is a time-delayed implementation, in which with step b), i. the addition of the base (B), although starting after the start of step a) is started. If a base (B) which has free NH or NH 2 groups is used in the process according to the invention, step b) is carried out, for example the addition of the oligoamine, however, preferably after the reaction in step a). Preference is given to using bases (B) which, in process step b), form salts which are already present in
- Step a) of the process according to the invention is preferably carried out at temperatures of 50 to 25O 0 C.
- temperatures of from 50 to 220 ° C., in particular from 80 ° C. to 150 ° C. have proven to be particularly advantageous. Since step a) is usually exothermic, it is preferably carried out with cooling.
- steps b) and c) of the process according to the invention are preferably carried out at temperatures from 0 to 250 0 C, preferably at temperatures of 20 to 150 0 C and more preferably at temperatures of 50 to 100 ° C.
- the temperature during steps b) and c) preferably remains within one Temperature frame of preferably 30 0 C, particularly preferably from 20 0 C constant. Since step b) is usually exothermic, it is preferably carried out with cooling.
- reaction steps are preferably carried out under inert gas, e.g. Nitrogen or argon performed.
- inert gas e.g. Nitrogen or argon performed.
- the inventive method may also have one or more of the following additional process steps: al) if the amine of the general formula (2) in step a) was used in excess, this excess can still before the addition of the base (B) in step b) are completely or partially separated.
- the separation is preferably carried out by distillation. This measure is preferably used to reduce the solubility of the respective salts or in the organic phase.
- d) Adding one or more nonpolar solvents (L) to the product-containing phase.
- the additional solvent (L) can be carried out before or after process steps a), al) b) and c). This measure is preferably used to reduce the solubility of the respective salts or in the organic phase.
- the salts precipitated in this step are preferably separated in an additional separation step, eg filtration.
- the amounts of salt to be separated are extremely low compared with the original amount of salt in step c), the separation is correspondingly simple.
- the addition of the nonpolar solvent before or during step c) the respective salts from the product phase in the liquid phase, the substantially from The halide of the base (B) consists, pushed and separated together with this, Distillative separation or purification of the product of the general formula (1) and the used in step a) optionally in excess and in the
- step b liberated (aminoorganyl) silane of the general formula (2).
- the (aminoorganyl) silane of the general formula (2) is preferably obtained directly in sufficiently high purity, so that it can be used again without further workup in the next reaction cycle.
- the product of the general formula (1) is preferably obtained in sufficient purity in the corresponding distillation.
- R-3 is hydrogen and at the same time at least one radical of the two radicals R ⁇ or R ⁇ from a hydrocarbon chain having at least 3
- Carbon atoms, the silylorganoamines in particular tend to be at elevated temperatures and under vacuum, that is conditions such as e.g. occur during distillation, to an inter- or intramolecular displacement of an alkoxy radical by the NH group to form
- Ring opening reactions of the silylorganoamine of the general formula (1) formed azasilacycles with alcohol usually proceed under mild conditions in a temperature range of 10 to 100 0 C, preferably from 15 ° C to 50 0 C, the optimum reaction conditions are in individual cases by preliminary experiments easily to investigate.
- (Aminoorganyl) silane of the general formula (2) it is also possible to add an excess of alcohol to the distilled starting material and distill the excess after completion of the reaction under more gentle conditions than the distillation conditions of ⁇ aminoorganyl) silane of the general formula (2), so that a Recycling is largely avoided.
- the ring-opening reactions of the azasilacycles from (aminoorganyl) of the formula silane (2) formed with alcohol extend generally under mild conditions in a temperature range of 10 to 100 0 C, preferably from 15 0 C to 50 0 C, the optimal reaction conditions are in each case easily determined by preliminary tests. If residues of the base (B) remain in the organic phase during the phase separation in step c), these are likewise preferably removed by distillation. The same applies to the optionally additionally added solvent (L) in step d).
- ⁇ Aminoorganyl) silane of the general formula (2) are removed by distillation, wherein the crude product initially remains in the distillation bottoms and is then purified in a separate distillation or thin-film evaporation step. f) Additional addition of ammonia to the product-containing phase after the phase separation in step c) and separation of the resulting ammonium halide. This measure may be particularly suitable for reducing the halide content in the final product.
- alkali metal alcoholates preferably sodium or potassium alkoxides, or alkali metal phosphates, preferably sodium or potassium phosphates or the respective hydrogen or dihydrogen phosphates
- This measure can be particularly suitable for reducing the halide content in the final product
- This measure can be used to bind any residues of halogen compounds, in particular ionic halides, so that they remain in a final distillation of the product of general formula (1) (see step e) largely in the distillation bottoms and a corresponding halide-poor product is obtained.
- step b) Aldehydes to the product-containing phase after step c) or else to the (aminoorganyl) silane fractions distilled under step e). If the base (B) added in step b) is a compound containing primary amino groups, this measure can serve to convert residues of the base (B) still present in these phases into the corresponding imines. The latter can often be Distillatively easier from the products and especially from the excessively used and / or in step b) released again (aminoorganyl) silanes of the general formula (2) as the base (B) itself.
- step b 1) Recovery of the base (B) used in step b), preferably by re-salting the resulting halide of this base with strong bases, e.g. Alkali or alkaline earth hydroxides, carbonates, bicarbonates, etc.
- the respective bases can be used in bulk or in aqueous or non-aqueous solution or suspension. If aqueous solutions are used and / or water is liberated during the reaction, this is preferably separated by distillation from the base (B). If ethylene diamine was used as the base (B), this separation by distillation is preferably carried out at such a high pressure that ethylenediamine and water no longer form an azeotrope.
- the base (B) is a compound, e.g. an amine that is itself reactive to the
- the (aminoorganyl) silane of the general formula (2) is preferably purified to such an extent by the said process steps that the content of the base (B) in the (aminoorganyl) silane of the general formula (2) less than 3%, preferably less than 1% and especially less than 0.5%, in each case by weight.
- a solvent (L) is used in step d), the boiling point of which is below that of the
- the process may be both batchwise, e.g. in stirred kettles, as well as being carried out continuously.
- the latter e.g. by the steps a), b) and optionally further steps (see above) in a tubular reactor or a Rhackgefäßkaskade done.
- the individual substances are here together or else - preferably - metered and mixed in succession.
- suitable methods e.g. using resting or settling vessels, decanters, etc., known and widely described in the literature.
- the base (B) chosen are compounds whose boiling point is determined both by the product of the general formula (1) and its cyclization products
- Azysilacyclene of the general formulas (4a) and (4b) as well as (aminoorganyl) silane of the general formula (2) by at least 40 ° C, preferably at least 60 0 C and more preferably at least 90 0 C different, so that residues of Base (B), which remain in the organic phase during the phase separation in step c), sufficiently well by distillation both from the product of the general formulas (1) or (4a) or (4b) and from the (aminoorganyl) silane can be separated off general formula (2).
- base (B) are preferably ethylene or
- the oligoamines (O) preferably contain 1 to 20, in particular 1 to 10, ethylene or propylenediamine units.
- Preferred oligoamines (O) are ethylenediamine, diethylenetriamine, diazabicyclooctane, pentamethyldiethylenetriamine, propylenediamine, N, N'-bis (3-aminopropyl) ethylenediamine.
- Ethylenediamine is particularly preferably used as base (B).
- base (B) ethylenediamine exhibits the following surprising combination of properties:
- step b) The addition of ethylenediamine leads in step b) already to a substantially complete salification, if only the particularly preferred amount of ethylene diamine from 0.8 to 2 equivalents based on the amount of
- the salt phase obtained by the extensive salification has a melting point of about 80 0 C.
- the liquid salt phase separates completely after a few minutes from the organic phase and can thus be separated without a large and therefore costly time required for a phase separation.
- the water content of the individual components, in particular the bases (B) to be used and optionally to be used solvent (L) is therefore preferably 0 to 20,000 ppm, preferably 0 to 5000 ppm, more preferably 0 to 2000 ppm, each based on the weight.
- Silylorganoamine of the general formula (!) In good to very easy good yields are obtained. The methods can be implemented on an industrial scale simply and safely.
- silylorganoamines of the general formula (1) are: (MeO) 3Si-CH 2 CH 2 CH 2 -NH-CH 2 CH 2 CH 2 -si (OMe) 3
- alkoxy radicals can be introduced into a molecule (for example methoxy and ethoxy radicals).
- methoxy and ethoxy radicals for example methoxy and ethoxy radicals.
- the purity of the bis- and tris (silylorgano) amines according to the invention of the general formula (1) including possibly formed in the synthesis or distillation of the target product Azasilacyclen of the general formulas (4a) and (4b) is preferably at least 85%, more preferably at least 95%.
- the purity can be increased to over 95% by means of an optional downstream distillation step e) of the product.
- the process according to the invention has the advantage that the majority of the by-produced ammonium salts of the (aminoorganyl) silanes of the general formula (2) need not be separated off as solid, which is usually the case on an industrial scale in the case of poorly crystallizing ammonium salts consuming and expensive.
- many so-called multi-purpose systems do not have sufficiently powerful equipment elements (e.g., centrifuges) for separating such large quantities of solids. By resalling, two liquid phases can now be separated from each other. In addition, washing steps of the filter cake with additional ein lymphdem solvent are unnecessary.
- Step a) would be consumed for the formation of the corresponding ammonium salts, by the resalendering with the generally relatively inexpensive base (B), for example ethylenediamine, recover and thereby make them available for recycling.
- B for example ethylenediamine
- Chloropropyltrimethoxysilane added. It was stirred for 60 min. Thereafter, the temperature was lowered to 105 0 C and 90 g of ethylenediamine and 50 g of o-xylene were added to the mixture within 10 minutes with stirring, whereby phase separation occurred. At the same temperature was further stirred for 30 min, with cooling to 70 0 C and then the heavier ethylenediamine hydrochloride phase was separated.
- the upper phase was treated with 6 g of a polyethyleneimine having a viscosity of 5 Pas at 2O 0 C (Lupasol ® G20 anhydrous (BASF AG)) and after removal of the low boilers (predominantly o-xylene, vacuum to 100 0 C / 10 mbar) distilled on a two-stage thin-film evaporator in vacuo.
- a polyethyleneimine having a viscosity of 5 Pas at 2O 0 C Liupasol ® G20 anhydrous (BASF AG)
- the low boilers predominantly o-xylene, vacuum to 100 0 C / 10 mbar
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
L'invention a pour objet un procédé de production de silyl-organoamines de la formule générale (1) R'3-nR1
nSi-R2-NR3-R4-SiR"3-mR5
m (1), par réaction de (amino-organyl) silanes de la formule générale (2) avec des (halogéno-organyl) silanes de la formule générale (3) R'3-nR1
nSi-R2-X (3), dans laquelle R', R'', R1, R2, R3, R4, R5, X, m et n ont les significations indiquées dans la revendication 1. La réaction comprend les étapes suivantes : a) réaction du (halogéno-organyl) silane de la formule générale (3) et du (amino-organyl) silane de la formule générale (2) à une température comprise entre 0 et 250 °C, ce qui produit, outre la silyl-organoamine de la formule générale (1), l'halogénure d'ammonium du (amino-organyl) silane de la formule générale (2), en tant que produit secondaire; b) addition d'une base (B), ce qui produit une décomposition double, partielle ou totale, qui libère à nouveau le (amino-organyl) silane de la formule générale (2) et forme l'halogénure de la base (B), l'halogénure de la base (B) étant liquide à des températures maximales de 200 °C; et c) séparation de l'halogénure liquide formé de la base (B).
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102009000500A DE102009000500A1 (de) | 2009-01-30 | 2009-01-30 | Verfahren zur Herstellung von Bis- und Tris(silylorgano)aminen |
PCT/EP2010/050576 WO2010086254A1 (fr) | 2009-01-30 | 2010-01-19 | Procédé de production de bis et tris(silyl-organo)amines |
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EP2384330A1 true EP2384330A1 (fr) | 2011-11-09 |
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EP10700566A Withdrawn EP2384330A1 (fr) | 2009-01-30 | 2010-01-19 | Procédé de production de bis et tris(silyl-organo)amines |
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US (1) | US20110282088A1 (fr) |
EP (1) | EP2384330A1 (fr) |
JP (1) | JP2012516296A (fr) |
KR (1) | KR20110093933A (fr) |
CN (1) | CN102300869A (fr) |
DE (1) | DE102009000500A1 (fr) |
WO (1) | WO2010086254A1 (fr) |
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KR101367190B1 (ko) * | 2011-12-27 | 2014-02-26 | 제이에스아이실리콘주식회사 | 트리스(알콕시실릴)아민의 제조 방법 및 트리실릴아민의 제조 방법 |
CN104086584A (zh) * | 2014-07-29 | 2014-10-08 | 荆州市江汉精细化工有限公司 | 一种双-(烷氧基硅丙基)-胺的制备方法 |
DE102015225883A1 (de) * | 2015-12-18 | 2017-06-22 | Evonik Degussa Gmbh | Bis(alkylalkoxysilyl)amin-reiche Zusammensetzungen, ein Verfahren zur deren Herstellung und deren Verwendung |
DE102015225879A1 (de) * | 2015-12-18 | 2017-06-22 | Evonik Degussa Gmbh | Tris-(alkylalkoxysilyl)amin-reiche Zusammensetzungen, deren Herstellung und deren Verwendung |
EP3397674B1 (fr) * | 2016-11-02 | 2019-07-10 | Wacker Chemie AG | Procédé pour la préparation de polysiloxanes à fonctionnalité sioh |
WO2019122750A1 (fr) * | 2017-12-22 | 2019-06-27 | Compagnie Generale Des Etablissements Michelin | Composé comprenant au moins deux groupements trialcoxysilyles, son utilisation à titre d'agent de fonctionnalisation d'élastomère diénique, élastomère diénique modifié et composition le contenant |
CN110835355A (zh) * | 2018-08-15 | 2020-02-25 | 张家港市国泰华荣化工新材料有限公司 | 高纯度双[(3-三烷氧基硅基)-丙基]胺的合成工艺 |
CN109970785B (zh) * | 2019-05-08 | 2024-04-26 | 安徽硅宝有机硅新材料有限公司 | 连续法合成双(3-三甲氧基甲硅烷基丙基)胺的成套设备 |
CN112480161B (zh) * | 2019-09-11 | 2023-02-28 | 新特能源股份有限公司 | 一种氨丙基三甲氧基硅烷及制备方法 |
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DE1905100B2 (de) * | 1969-02-01 | 1977-10-20 | Bayer Ag, 5090 Leverkusen | Siloxanmodifizierte harnstoffderivate |
US4526996A (en) | 1984-06-19 | 1985-07-02 | Union Carbide Corporation | Process for the preparation of N-substituted aminoalkylsilanes |
US4659798A (en) * | 1985-06-24 | 1987-04-21 | Union Carbide Corporation | Novel room temperature vulcanizable polydiorganosiloxane compositions |
US4775415A (en) * | 1986-08-06 | 1988-10-04 | First Brands Corporation | Alcohol-based aluminum corrosion inhibitor compositions comprising polysilyl compounds |
US5101055A (en) * | 1991-09-09 | 1992-03-31 | Dow Corning Corporation | Process for preparation of bis- and tris(silylorgano)amines |
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DE19652642A1 (de) * | 1996-12-18 | 1998-06-25 | Degussa | Kontinuierliches Verfahren zur Herstellung von gamma-Aminopropyltrialkoxysilanen |
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US6417381B1 (en) | 2001-11-15 | 2002-07-09 | Crompton Corporation | Process for preparing bis(silylorgano)amines |
US6452033B1 (en) * | 2002-02-11 | 2002-09-17 | Dow Corning Corporation | Method of making N-[2-aminoethyl] aminoalkylalkoxysilanes with ethyenediamine salt recycle |
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2009
- 2009-01-30 DE DE102009000500A patent/DE102009000500A1/de not_active Withdrawn
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2010
- 2010-01-19 KR KR1020117015521A patent/KR20110093933A/ko active IP Right Grant
- 2010-01-19 CN CN2010800061306A patent/CN102300869A/zh active Pending
- 2010-01-19 JP JP2011546776A patent/JP2012516296A/ja active Pending
- 2010-01-19 WO PCT/EP2010/050576 patent/WO2010086254A1/fr active Application Filing
- 2010-01-19 US US13/142,622 patent/US20110282088A1/en not_active Abandoned
- 2010-01-19 EP EP10700566A patent/EP2384330A1/fr not_active Withdrawn
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US20110282088A1 (en) | 2011-11-17 |
WO2010086254A1 (fr) | 2010-08-05 |
DE102009000500A1 (de) | 2010-08-05 |
JP2012516296A (ja) | 2012-07-19 |
CN102300869A (zh) | 2011-12-28 |
KR20110093933A (ko) | 2011-08-18 |
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