DE60209541T2 - Verfahren zur Herstellung von sekundären und tertiären Amino-funktionellen Silanen - Google Patents
Verfahren zur Herstellung von sekundären und tertiären Amino-funktionellen Silanen Download PDFInfo
- Publication number
- DE60209541T2 DE60209541T2 DE60209541T DE60209541T DE60209541T2 DE 60209541 T2 DE60209541 T2 DE 60209541T2 DE 60209541 T DE60209541 T DE 60209541T DE 60209541 T DE60209541 T DE 60209541T DE 60209541 T2 DE60209541 T2 DE 60209541T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- carbon atoms
- hydrocarbon group
- hydrogen
- aminoorganosilane
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 31
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000004756 silanes Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 15
- -1 silane compound Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 8
- 229910000077 silane Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 150000002466 imines Chemical group 0.000 description 21
- 150000001412 amines Chemical class 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 15
- 238000006722 reduction reaction Methods 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 13
- 150000002576 ketones Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 7
- 150000003949 imides Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CDRHUURBSOCCDK-UHFFFAOYSA-N 1-phenyl-n-(3-triethoxysilylpropyl)methanimine Chemical compound CCO[Si](OCC)(OCC)CCCN=CC1=CC=CC=C1 CDRHUURBSOCCDK-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 5
- 239000002318 adhesion promoter Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- MDWZOAUWADLKNG-UHFFFAOYSA-N 1-phenyl-n-(3-trimethoxysilylpropyl)methanimine Chemical compound CO[Si](OC)(OC)CCCN=CC1=CC=CC=C1 MDWZOAUWADLKNG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 125000004416 alkarylalkyl group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- UVEWQKMPXAHFST-SDNWHVSQSA-N chembl1256376 Chemical compound C=1C=CC=CC=1/C=N/C1=CC=CC=C1 UVEWQKMPXAHFST-SDNWHVSQSA-N 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- GVDZNWFGNHAZCX-UHFFFAOYSA-N 1-phenyl-n-propan-2-ylmethanimine Chemical compound CC(C)N=CC1=CC=CC=C1 GVDZNWFGNHAZCX-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 239000013466 adhesive and sealant Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 150000004658 ketimines Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 2
- QLBIJVOHMKFIQB-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)cyclohexanimine Chemical compound CO[Si](OC)(OC)CCCN=C1CCCCC1 QLBIJVOHMKFIQB-UHFFFAOYSA-N 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 1
- KYEACNNYFNZCST-UHFFFAOYSA-N 1-methylpyrrolidine-2,5-dione Chemical compound CN1C(=O)CCC1=O KYEACNNYFNZCST-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 2-methylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C)C(=O)C2=C1 ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- BMZZGIWIRFMFOU-UHFFFAOYSA-N 4-cyclohexylidenebutan-1-amine Chemical compound NCCCC=C1CCCCC1 BMZZGIWIRFMFOU-UHFFFAOYSA-N 0.000 description 1
- RMLNAEPKTRCSRH-GDVGLLTNSA-N C1[C@@H]2NCCCC12 Chemical compound C1[C@@H]2NCCCC12 RMLNAEPKTRCSRH-GDVGLLTNSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N Glycerol trihexadecanoate Natural products CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- MZSSRMMSFLVKPK-UHFFFAOYSA-N acetaldehyde ammonia trimer Chemical compound CC1NC(C)NC(C)N1 MZSSRMMSFLVKPK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000004705 aldimines Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002081 enamines Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N lauric acid triglyceride Natural products CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XZRLSZCBYSWKMI-UHFFFAOYSA-N n-propan-2-ylcyclohexanimine Chemical compound CC(C)N=C1CCCCC1 XZRLSZCBYSWKMI-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-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
- 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
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US990959 | 1992-12-15 | ||
| US09/990,959 US6586612B2 (en) | 2001-11-16 | 2001-11-16 | Process for the preparation of secondary and tertiary amino-functional silanes, iminoorganosilanes and/or imidoorganosilanes |
| PCT/US2002/035350 WO2003044026A1 (en) | 2001-11-16 | 2002-11-04 | Process for the preparation of secondary and tertiary amino-functional silanes, iminoorganosilanes and/or imidoorganosilanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60209541D1 DE60209541D1 (de) | 2006-04-27 |
| DE60209541T2 true DE60209541T2 (de) | 2006-12-21 |
Family
ID=25536688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60209541T Expired - Lifetime DE60209541T2 (de) | 2001-11-16 | 2002-11-04 | Verfahren zur Herstellung von sekundären und tertiären Amino-funktionellen Silanen |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6586612B2 (enExample) |
| EP (1) | EP1451198B1 (enExample) |
| JP (1) | JP4436678B2 (enExample) |
| KR (1) | KR20050043791A (enExample) |
| AU (1) | AU2002354009A1 (enExample) |
| BR (1) | BR0214262A (enExample) |
| DE (1) | DE60209541T2 (enExample) |
| WO (1) | WO2003044026A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005056051A1 (de) | 2005-11-24 | 2007-05-31 | Wacker Chemie Ag | Verfahren zur Herstellung von beta-Ketocarbonyl-funktionellen Organosiliciumverbindungen |
| US7442821B2 (en) * | 2005-11-28 | 2008-10-28 | Momentive Performance Materials Inc. | Process for preparing unsaturated imidoalkoxysilanes |
| KR100843201B1 (ko) | 2006-08-30 | 2008-07-02 | 삼성전자주식회사 | 패키지 커팅용 장비 및 그 장비를 이용한 패키지 커팅 방법 |
| KR100845520B1 (ko) * | 2007-02-08 | 2008-07-10 | 연세대학교 산학협력단 | 이방성 도전필름용 코어하드볼의 제조방법 |
| US20090165676A1 (en) * | 2007-12-26 | 2009-07-02 | E.I. Du Pont De Nemours And Company | Bis(n-silylalkyl)aspartimides and processes therefor |
| US20090203826A1 (en) * | 2008-02-13 | 2009-08-13 | Michael Joseph Rachita | Methods of making siloxy-imine functionalized rubbery polymers and uses thereof in rubber compositions for tires |
| US8022159B2 (en) * | 2008-11-24 | 2011-09-20 | The Goodyear Tire & Rubber Company | Terminating compounds, polymers, and their uses in rubber compositions and tires |
| JP5954877B2 (ja) * | 2010-03-11 | 2016-07-20 | エージェンシー フォー サイエンス，テクノロジー アンド リサーチ | 負荷率の改善が可能な抗癌剤送達ビヒクル |
| KR101460352B1 (ko) * | 2014-02-28 | 2014-11-10 | 동우 화인켐 주식회사 | 점착제 조성물 |
| TWI716333B (zh) * | 2015-03-30 | 2021-01-11 | 法商液態空氣喬治斯克勞帝方法研究開發股份有限公司 | 碳矽烷與氨、胺類及脒類之觸媒去氫耦合 |
| FR3050207B1 (fr) * | 2016-04-15 | 2018-04-06 | Ecole Superieure De Physique Et De Chimie Industrielles De La Ville De Paris | Composition de polymeres comprenant des silicones reticules a points de reticulation echangeables, procede de preparation et utilisations |
| JP6252716B1 (ja) | 2016-06-24 | 2017-12-27 | Jsr株式会社 | 変性共役ジエン系重合体の製造方法、変性共役ジエン系重合体、重合体組成物、架橋体、タイヤ及び化合物 |
| EP3484898B1 (en) | 2016-07-15 | 2023-06-28 | Momentive Performance Materials Inc. | Method of stabilizing imino-functional silane |
| JP6947084B2 (ja) * | 2018-03-05 | 2021-10-13 | 信越化学工業株式会社 | イミン構造含有オルガノキシシラン化合物の製造方法 |
| CN114585663A (zh) | 2019-08-20 | 2022-06-03 | 高新特殊工程塑料全球技术有限公司 | 基于聚(苯醚)的增容材料 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2513996A (en) | 1947-12-19 | 1950-07-04 | Shell Dev | Reaction of a primary amine with an imine |
| US2582128A (en) | 1950-02-11 | 1952-01-08 | Rohm & Haas | Aldimines |
| US2942019A (en) * | 1956-10-12 | 1960-06-21 | Union Carbide Corp | Organosilicon methylideneamino compounds and process for producing the same |
| US3755354A (en) * | 1969-05-05 | 1973-08-28 | Gen Electric | Amide acid and imido-substituted organosilanes |
| SU353547A1 (ru) * | 1970-11-16 | 1977-07-25 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср | Способ получени кремнийорганических аминов |
| US3681420A (en) * | 1971-03-03 | 1972-08-01 | Quaker Oats Co | N,n{40 -bis{8 tri (substituted)silylalkylene{9 -1,4-xylene-{60 ,{60 {40 -diimine |
| US3737430A (en) * | 1971-03-03 | 1973-06-05 | Quaker Oats Co | N,n'-bis((tri(substituted))silylalkylene)-1,4-xylene-alpha,alpha'-diimine |
| US3681287A (en) * | 1971-03-03 | 1972-08-01 | Quaker Oats Co | Siliceous materials bound with resin containing organosilane coupling agent |
| DE2525295C3 (de) | 1975-06-06 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Azomethinen |
| US4088668A (en) * | 1977-07-01 | 1978-05-09 | Merrell Toraude Et Compagnie | Acetylene derivatives |
| US4378250A (en) | 1981-07-31 | 1983-03-29 | Treadway Gerald D | Organosilicone coating compositions |
| DE3414877A1 (de) * | 1984-04-19 | 1985-10-24 | Henkel KGaA, 4000 Düsseldorf | Polyurethanzubereitungen mit inkorporiertem haftvermittler |
| JPH0616179B2 (ja) * | 1984-12-24 | 1994-03-02 | 富士ゼロックス株式会社 | 電子写真現像剤 |
| US4832748A (en) * | 1986-10-21 | 1989-05-23 | Toagosei Chemical Industry Co., Ltd. | Coating composition |
| JP3483999B2 (ja) * | 1995-09-14 | 2004-01-06 | 東レ・ダウコーニング・シリコーン株式会社 | プリプレグおよびガラス繊維強化樹脂成形物 |
| US5866262A (en) | 1995-10-16 | 1999-02-02 | Galic Maus Ventures | Fully-hydrolized ketimine silane/epoxide silane copolymer liquid hardcoating compositions and processes for dipcoating polycarbonate spectacle lenses |
| JP3831437B2 (ja) * | 1995-11-15 | 2006-10-11 | 東レ・ダウコーニング株式会社 | シランカップリング剤およびその製造方法 |
| US5840961A (en) * | 1996-07-12 | 1998-11-24 | G. D. Searle & Co. | Asymmetric synthesis of chiral beta-amiNo acids |
| US6072085A (en) | 1997-09-30 | 2000-06-06 | Massachusetts Institute Of Technology | Imine hydrosilylation, uses and reagents related thereto |
| JP3427742B2 (ja) | 1998-07-30 | 2003-07-22 | 信越化学工業株式会社 | 硬化性樹脂組成物及び接着剤 |
| US6191286B1 (en) * | 1998-08-26 | 2001-02-20 | Osi Specialties Inc. | Imidosilane compositions |
| JP3969101B2 (ja) * | 2001-01-31 | 2007-09-05 | 日立化成工業株式会社 | 封止用エポキシ樹脂成形材料及び電子部品装置 |
-
2001
- 2001-11-16 US US09/990,959 patent/US6586612B2/en not_active Expired - Lifetime
-
2002
- 2002-11-04 AU AU2002354009A patent/AU2002354009A1/en not_active Abandoned
- 2002-11-04 EP EP02789413A patent/EP1451198B1/en not_active Expired - Lifetime
- 2002-11-04 WO PCT/US2002/035350 patent/WO2003044026A1/en not_active Ceased
- 2002-11-04 JP JP2003545663A patent/JP4436678B2/ja not_active Expired - Fee Related
- 2002-11-04 DE DE60209541T patent/DE60209541T2/de not_active Expired - Lifetime
- 2002-11-04 KR KR1020047007479A patent/KR20050043791A/ko not_active Ceased
- 2002-11-04 BR BR0214262-7A patent/BR0214262A/pt not_active IP Right Cessation
-
2003
- 2003-06-10 US US10/458,036 patent/US6998499B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1451198A1 (en) | 2004-09-01 |
| AU2002354009A1 (en) | 2003-06-10 |
| US20030220513A1 (en) | 2003-11-27 |
| DE60209541D1 (de) | 2006-04-27 |
| EP1451198B1 (en) | 2006-03-01 |
| US20030097014A1 (en) | 2003-05-22 |
| BR0214262A (pt) | 2004-09-21 |
| US6998499B2 (en) | 2006-02-14 |
| JP2005509682A (ja) | 2005-04-14 |
| US6586612B2 (en) | 2003-07-01 |
| JP4436678B2 (ja) | 2010-03-24 |
| WO2003044026A1 (en) | 2003-05-30 |
| KR20050043791A (ko) | 2005-05-11 |
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