18418-72-9Relevant articles and documents
Synthesis and reactivity of bis(triethoxysilyl)methane, tris(triethoxysilyl)methane and some derivatives
Corriu, Robert J.P.,Granier, Michel,Lanneau, Gerard F.
, p. 79 - 88 (1998)
Syntheses of new poly(trifunctional-silyl)alkanes, which are potent coupling agents of hybrid organic-inorganic materials have been thoroughly examined. Optimization of the Benkeser reaction using chloroform, trichlorosilane and tri-n-butylamine (respective ratios 1:4.5:3) afforded bis(trichlorosilyl)methane isolated as bis(triethoxysilyl)methane after ethanolysis (overall yield 60%). With nine equivalents of trichlorosilane, tris(trichlorosilyl)methane is preferentially formed, isolated as tris(triethoxysilyl)methane (30% yield). C-Substituted bis(triethoxysilyl) methanes were obtained after metallation of the α-carbon and trapping experiments with the corresponding alkyl halides. In the case of tris(triethoxysilyl)carbanion, only MeI and Br2 were able to give the anticipated products. Unexpectedly, CO2 insertion afforded the stable ketene, [(EtO)3Si]2C=C=O.
Enhanced hydrolytic stability of siliceous surfaces modified with pendant dipodal silanes
Arkles, Barry,Pan, Youlin,Larson, Gerald L.,Singh, Mani
, p. 9442 - 9450 (2014/08/05)
Dipodal silanes possess two silicon atoms that can covalently bond to a surface. They offer a distinct advantage over conventional silanes commonly used for surface modification in terms of maintaining the integrity of surface coatings, adhesive primers, and composites in aqueous environments. New nonfunctional and functional dipodal silanes with structures containing pendant rather than bridged organofunctionality are introduced. The stability of surfaces in aqueous environments prepared from dipodal silanes with hydrophobic alkyl functionality is compared to the stability of similar surfaces prepared from the conventional silanes. In strongly acidic and brine environments, surfaces modified with dipodal silanes demonstrate markedly improved resistance to hydrolysis compared to surfaces prepared from conventional silanes. Pendant dipodal silanes exhibit greater stability than bridged dipodal silanes. The apparent equilibrium constant for the formation of silanol species by the hydrolysis of a disiloxane bond was determined as Kc=[SiOH]2/[Si-O-Si][H2O]= 6±1×10-5 and is helpful in understanding the enhanced hydrolytic stability of surfaces modified with dipodal silanes. Two feet are better than one! Nonfunctional and functional dipodal silanes with structures containing pendant rather than bridged organofunctionality were synthesized. Surfaces modified with pendant dipodal silanes were found to be more resistant to hydrolysis than the bridged structure with single-carbon separated (disilapropyl)silanes, demonstrating the greatest resistance to hydrolysis and best stability (see figure).