Lepidimoide is a naturally occurring disaccharide reported to be an oligosaccharin, i.e. to exhibit ‘hormone-like’ biological activity. It was found in cress (Lepidium sativum) root exudates and exerts apparently allelopathic effects on neighbouring Amaranthus seedlings. In the present study the effect of cress root exudates on hypocotyl and root length of Amaranthus caudatus and Lactuca sativa was studied. The seedlings of both species grown with Lepidium sativum seedlings had longer hypocotyls and shorter roots as compared to the control. In this study I found an active principle with biological effects similar to those of lepidimoide to be more abundant in cress seed-coat mucilage than in root exudates. The active principle peaked 24 hours after seed soaking, and thereafter plateaued. I also for the first time confidently proved that the bioactive compound(s) were exuded by cress and were not microbial digestion products or seed treatment chemicals. Quantitative tests of cress root exudates and cress seed-coat mucilage showed the presence of hexoses, pentoses, uronic acids and unsaturated uronic acid. The presence of unsaturated uronic acid might be of interest because the known structure of lepidimoide includes an unsaturated uronic acid. Active principle from mucilage was partitioned into the aqueous phase when shaken with ethyl acetate at pH 2, 6.5 and 12, showing it to be hydrophilic, unlike auxins and gibberellins. The mucilage was also heated at 130°C for 48 h and severe heating did not affect its biological activity, suggesting that if the compound is lepidimoide then it is heat-resistant. In an attempt to test whether the compound is of high or low Mr, the mucilage was partitioned into 75% ethanol-precipitated and non-precipitated fractions. The biological activity in the non-precipitated fraction was very high, and was further separated by gel-permeation chromatography (GPC). GPC on Bio-Gel P-10 and P-2 suggested that the active principle had Mr ~500–750, compatible with oligosaccharide(s), suggesting that a particular oligosaccharide may be the active principle. TLC separation of bioactive fractions from P-2 showed that the bioactive compound migrated between GalA and Gal but co-migrated with sucrose; however, paper chromatography separation proved that the compound is not sucrose and might be a different disaccharide (lepidimoide). From the structure of lepidimoide, Fry et al. (1993) proposed that lepidimoide is formed by the lyase-catalysed cleavage of a pectic polysaccharide, rhamnogalacturonan-I (RG-I). So I tried to prepare lepidimoide or lepidimoide-like compounds by the action of RG-I lyase from Pichia pastoris on purified potato RG-I. The lyase showed its activity but the digest did not demonstrate biological activity, which might be due to presence of tris-HCl buffer in the solution. An attempt was also made to prepare lepidimoide by methyl esterification and -elimination of purified potato RG-I but again the product did not show any biological activity, which might be due to presence of borate buffer in the solution. This part of research might be useful for future work on preparation of lepidimoide and lepidimoide-like compounds.

This thesis reports the studies on the reaction of 1-azabutadienes with PhCH2Re(CO)5 to prepare the cyclometallated azabutadiene tetracarbonyl compounds. Three 1-azabutadienes with different reactivity on the N and C-1 carbons were prepared and their reactions with PhCH2Re(CO)5 were investigated. All the reactions gave a mixture of the cyclorheniated azabutadienes and the isomers of the substituted derivatives formed by substitution by a second azabutadiene. The substituted derivatives as the mixture were always the main products of the reactions and were obtained in good-to-excellent yield even under modified conditions intended to optimise the yield of the cyclorheniated azabutadienes. The yield could not be improved beyond 30 %. Isomerisation of the azabutadiene about the N=C bond provided very rare cis-azabutadiene metal complexes. NMR studies on the mixture of the two isomers and suggested that the product ratio depended on the molar ratio of PhCH2Re(CO)5 in the reaction mixtures. The reactions gave the Re analogues of the products obtained in the corresponding Mn reactions. All the compounds were characterised spectroscopically as well as by microanalysis and examples of all three types were structurally determined by X-ray crystallography. The reactions of the substituted derivative as the mixture of the two isomers with unsaturated molecules including phenyl acetylene, p-methoxyphenyl isocyanide, and phenyl isocyanate and methyl acrylate were investigated.

Conventional disposal of waste rock results in the construction of benches with interbedded fine and coarse layers dipping at the angle of repose. The waste rock benches are typically 20-meters in height and are constructed in a vertical sequence to form waste rock dumps commonly greater than 100-meters high. The interbedded structure influences the flow pathways for infiltration water within the waste rock profile. Preferential flow pathways develop when one material becomes more conductive than the surrounding material. The flow of meteoric waters through the interbedded waste rock structure is difficult to describe since the dumps are constructed above natural topography and are generally unsaturated. Two previous research studies were undertaken at the University of Saskatchewan to study end dumped waste rock piles and the relationship to preferential flow for unsaturated conditions. The first study was conducted during the excavation of a large waste rock pile at Golden Sunlight Mine in Montana (Herasymuik, 1996). Field observations showed that the waste rock pile consisted of steeply dipping fine and coarse-grained layers. The results of further laboratory analysis indicated the potential for preferential flow through the fine-grained material under conditions with negative pore-water pressures and unsaturated flow. The second study investigated the mechanism for preferential flow in vertically layered, unsaturated soil systems (Newman, 1999). The investigation included a vertical two-layer column study and a subsequent numerical modelling program showing that water prefers to flow in the finer-grained material. The preferential flow path was determined to be a function of the applied surface flux rates and the unsaturated hydraulic conductivity of the fine-grained material layer. A numerical modelling program to evaluate preferential flow was conducted for the present study in an inclined four-layer system consisting of alternating fine and coarse-grained waste rock. The numerical modelling program was undertaken using the commercial seepage software package, Seep/W, that is commonly used by geotechnical engineers. The result obtained using Seep/W showed preferential flow to occur in the fine-grained layer. However, difficulties with respect to convergence under low flow conditions with steep hydraulic conductivity functions were encountered. A comprehensive sensitivity analysis was completed to investigate the factors that influence convergence in the Seep/W model including: convergence criteria, mesh design and material properties. It was found that the hydraulic conductivity function used for the coarse-grained material was the most important factor. The problem of the steep slope for the hydraulic conductivity function specified for the coarse-grained material was solved by progressively decreasing the slope of the hydraulic conductivity function at 10-8 m/s (for applied fluxes of 10-7 m/s or less). The sensitivity analysis showed that the manipulation of the hydraulic conductivity function had insignificant changes in the flux distribution between the waste rock layers and great significance for achieving convergence. Based on the discoveries of the sensitivity analysis, a 20-meter high multi-layer waste rock profile inclined at 50º with an applied flux of 7.7e10-9 m/s equal to the annual precipitation at the Golden Sunlight Mine was successfully simulated. A parametric study was subsequently conducted for an applied flux rate of 10-5 m/s for slope heights of 1-meter to 20 meters with slope angles varying between 45º and 90º. The parametric study demonstrated that flow in a multi-layered waste rock dump is a function of inclination, contact length between the layers, and the coarse and fine-grained hydraulic properties for the waste rock. An alternative numerical modelling technique based on a modified Kisch solution was also used to investigate preferential flow. The Kisch method helped to verify and simplify the numerical problem as well as to illustrate the mechanics of preferential flow in a two-layered system. In general, commercial seepage modeling packages are powerful and useful tools that are designed to adequately accommodate a wide range of geotechnical problems. The results of this research study indicate that Seep/W may not be the best-suited tool to analyze unsaturated seepage through sloped waste rock layers. However, numerical modelling is a process and working through the process helps to enhance engineering judgment. The Seep/W model provided an adequate solution for a simplified simulation of unsaturated seepage through waste rock layers. The modified Kisch solution independently verified the solution and provided additional confidence for the results of Seep/W model.

Conventional disposal of waste rock results in the construction of benches with interbedded fine and coarse layers dipping at the angle of repose. The waste rock benches are typically 20-meters in height and are constructed in a vertical sequence to form waste rock dumps commonly greater than 100-meters high. The interbedded structure influences the flow pathways for infiltration water within the waste rock profile. Preferential flow pathways develop when one material becomes more conductive than the surrounding material. The flow of meteoric waters through the interbedded waste rock structure is difficult to describe since the dumps are constructed above natural topography and are generally unsaturated. Two previous research studies were undertaken at the University of Saskatchewan to study end dumped waste rock piles and the relationship to preferential flow for unsaturated conditions. The first study was conducted during the excavation of a large waste rock pile at Golden Sunlight Mine in Montana (Herasymuik, 1996). Field observations showed that the waste rock pile consisted of steeply dipping fine and coarse-grained layers. The results of further laboratory analysis indicated the potential for preferential flow through the fine-grained material under conditions with negative pore-water pressures and unsaturated flow. The second study investigated the mechanism for preferential flow in vertically layered, unsaturated soil systems (Newman, 1999). The investigation included a vertical two-layer column study and a subsequent numerical modelling program showing that water prefers to flow in the finer-grained material. The preferential flow path was determined to be a function of the applied surface flux rates and the unsaturated hydraulic conductivity of the fine-grained material layer. A numerical modelling program to evaluate preferential flow was conducted for the present study in an inclined four-layer system consisting of alternating fine and coarse-grained waste rock. The numerical modelling program was undertaken using the commercial seepage software package, Seep/W, that is commonly used by geotechnical engineers. The result obtained using Seep/W showed preferential flow to occur in the fine-grained layer. However, difficulties with respect to convergence under low flow conditions with steep hydraulic conductivity functions were encountered. A comprehensive sensitivity analysis was completed to investigate the factors that influence convergence in the Seep/W model including: convergence criteria, mesh design and material properties. It was found that the hydraulic conductivity function used for the coarse-grained material was the most important factor. The problem of the steep slope for the hydraulic conductivity function specified for the coarse-grained material was solved by progressively decreasing the slope of the hydraulic conductivity function at 10-8 m/s (for applied fluxes of 10-7 m/s or less). The sensitivity analysis showed that the manipulation of the hydraulic conductivity function had insignificant changes in the flux distribution between the waste rock layers and great significance for achieving convergence. Based on the discoveries of the sensitivity analysis, a 20-meter high multi-layer waste rock profile inclined at 50º with an applied flux of 7.7e10-9 m/s equal to the annual precipitation at the Golden Sunlight Mine was successfully simulated. A parametric study was subsequently conducted for an applied flux rate of 10-5 m/s for slope heights of 1-meter to 20 meters with slope angles varying between 45º and 90º. The parametric study demonstrated that flow in a multi-layered waste rock dump is a function of inclination, contact length between the layers, and the coarse and fine-grained hydraulic properties for the waste rock. An alternative numerical modelling technique based on a modified Kisch solution was also used to investigate preferential flow. The Kisch method helped to verify and simplify the numerical problem as well as to illustrate the mechanics of preferential flow in a two-layered system. In general, commercial seepage modeling packages are powerful and useful tools that are designed to adequately accommodate a wide range of geotechnical problems. The results of this research study indicate that Seep/W may not be the best-suited tool to analyze unsaturated seepage through sloped waste rock layers. However, numerical modelling is a process and working through the process helps to enhance engineering judgment. The Seep/W model provided an adequate solution for a simplified simulation of unsaturated seepage through waste rock layers. The modified Kisch solution independently verified the solution and provided additional confidence for the results of Seep/W model.

The hydraulic-mechanical behaviour of swelling clay is examined in this thesis. The study includes laboratory testing and numerical modeling which considers the influence of boundary conditions on the hydraulic-mechanical behaviour of a compacted unsaturated swelling clay soil. The laboratory testing component of this research consists of three (3) series of tests using a newly modified triaxial apparatus on which mechanical and hydraulic boundary conditions are altered during liquid infiltration. Mechanical boundary conditions range from constant volume to constant mean stress and also include constant stiffness which is a spring type boundary consisting of both volume expansion and mean stress increase. Hydraulic boundary conditions include drained and undrained flow into triaxial specimens. The numerical modeling component of this research includes the creation of a new capillary tube model for swelling clay materials and incorporates dynamic changes to the cross-sectional area for flow. Laboratory results are modeled using the capillary tube model, an empirical hydraulic model, D’Arcy’s Law, and in an elastic-plastic context for unsaturated soil. Results of the laboratory and numerical modeling components show that boundary conditions dominate the hydraulic-mechanical behaviour of unsaturated swelling clay soil during liquid infiltration. In particular, a mechanism is shown to explain how hydraulic conductivity of a swelling soil can decrease with increasing water content at constant void ratio. Finally hydraulic and mechanical behaviour cannot be considered separately in swelling materials due to the intimate relationship in their response. / October 2006

The increasing use of ethanol as a gasoline additive has raised concerns over the potential impacts ethanol might have on groundwater contamination. In North America, 10% ethanol is commonly being added to gasoline (termed E10). Ethanol is usually denaturated with gasoline compounds before being transported; consequently E95 (95% ethanol) mixtures are also common. Therefore, spills with compositions ranging from E10 to E95 can be anticipated. The compounds of main concern associated with gasoline spills are benzene, toluene, ethylbenzene and xylenes (BTEX), trimethylbenzenes (TMBs) and naphthalene, due to their higher mobility and potential risks to human health. Ethanol is thought to increase mobility of the NAPL, create higher hydrocarbon concentrations in groundwater due to cosolvency, and decrease the rate of gasoline hydrocarbon biodegradation, with consequent increase in the length of the dissolved plumes. The objective of this research was to improve the knowledge about ethanol fate in the subsurface and the impacts it might have on the fate of gasoline compounds. To investigate that, laboratory experiments and controlled field tests supported by numerical modeling were conducted. To evaluate the impact of ethanol on dissolved hydrocarbon plumes, data from a controlled field test were evaluated using a numerical model. The mass discharge of BTEX, TMB and naphthalene from three sources (E0, E10 and E95) emplaced below the water table was compared to simulation results obtained in the numerical model BIONAPL/3D. It was shown that if ethanol fuel mixtures get below the water table, ethanol is dissolved and travels downgradient fast, in a short slug. Mass discharge from the E0 and E10 sources had similar hydrocarbon decay rates, indicating that ethanol from E10 had no impact on hydrocarbon degradation. In contrast, the estimated hydrocarbon decay rates were significantly lower when the source was E95. The aquifer did not have enough oxygen to support the mass loss observed assuming complete mineralization. Assuming a heterogeneous distribution of hydraulic conductivity did little to overcome this discrepancy. A better match between the numerical model and the field data was obtained assuming partial degradation of hydrocarbons to intermediate compounds, with consequent less demand for oxygen. Besides depending on the concentration of ethanol in the groundwater, the impact of ethanol on hydrocarbon degradation appears to be highly dependent on the aquifer conditions, such as availability of electron acceptors and adaptation of the microbial community. Another concern related to ethanol biodegradation is formation of explosive levels of methane. In this study, methane δ13C from toluene and ethanol as substrates was evaluated in microcosm tests. It was shown that methane is enriched in δ13C when ethanol is the substrate. Ethanol derived methane δ13C is in the range of -20‰ to 30‰, while methane from gasoline is around -55‰. The different ranges of δ13C allow it to be used as a tool to identify methane’s origin. This tool was applied to seven ethanol-gasoline contaminated sites. Methane origin could be clearly distinguished in five of the seven sites, while in the other two sites methane appears to have been produced from both ethanol and gasoline. Both ethanol and gasoline were identified as the source of methane in hazardous concentrations. The behaviour of ethanol fuels in the unsaturated zone was evaluated in 2-dimensional (2-D) lab tests and in a controlled field test. In the 2-D lab tests, dyed gasoline and ethanol were injected in the unsaturated zone simulated in a transparent plexiglass box packed with glass beads. Tests were performed under both static conditions and with horizontal groundwater flow. It was confirmed that some ethanol can be retained in the unsaturated zone pore water. However, most of the ethanol went through the unsaturated zone and reached the pre-existing gasoline pool. Ethanol displaced the NAPL to deeper positions, and it was shown that for large ethanol releases much of the gasoline can be displaced to below the water table. The ethanol that reaches the capillary fringe was shown to travel downgradient rapidly at the top of the capillary fringe, while ethanol was also retained in the unsaturated zone. The behaviour of ethanol fuel spills was further evaluated in a controlled field test. 200L of E10 containing around 5% MTBE was released into the unsaturated zone. Groundwater concentrations of ethanol, MTBE, BTEX, TMB and naphthalene above and below the water table were monitored downgradient of the source in multilevel wells. Lab tests were performed to evaluate the applicability of these samplers for volatile organic compounds. It was shown that volatilization losses might be significant when bubbles formation in the sampling line could not be avoided. A method for losses estimation and correction of the concentrations was developed. Concentrations in the source zone were measured in soil samples. Despite the thin (35 cm) unsaturated zone at the site, most of the ethanol was retained in the unsaturated zone pore water, above the capillary fringe. Being in zones of low effective hydraulic conductivity, ethanol was not transported downgradient, and remained in the unsaturated zone for more than 100 days. Ethanol mass discharge was much lower than would be anticipated based solely on the ethanol fraction in the gasoline and on its solubility. Oscillations in the water table, particularly when a shallow position was maintained for prolonged periods, flushed some ethanol to zones with high water saturation, where horizontal transport occurred. The ethanol that reaches the saturated zone appears in the downgradient wells as a slug, with relatively low concentrations. No effect of ethanol on gasoline hydrocarbons was observed, a consequence of most of the ethanol being retained in the unsaturated zone. In summary, spills of ethanol fuels might have two different outcomes, depending on whether most of the ethanol is retained in the unsaturated zone or if most reaches the capillary fringe and the saturated zone. The relation between the ethanol volume spilled and the retention capacity of the unsaturated zone will control the spill behaviour. The volume of ethanol that can be retained in the unsaturated zone is a function of the volume of water that is contacted by the infiltrating NAPL. Therefore, the type of soil, heterogeneities, depth to the water table and area of the spill will be determinant factors. If a relatively large volume of ethanol reaches the capillary fringe, ethanol will travel rapidly in the groundwater possibly in high concentrations, potentially enhancing dissolved hydrocarbon plumes. However, when most of the ethanol is retained in the unsaturated zone, it will likely be detected downgradient only in low concentration, and in pulses spread in time. In this scenario, impact on hydrocarbon plumes will be minor.

The increasing use of ethanol as a gasoline additive has raised concerns over the potential impacts ethanol might have on groundwater contamination. In North America, 10% ethanol is commonly being added to gasoline (termed E10). Ethanol is usually denaturated with gasoline compounds before being transported; consequently E95 (95% ethanol) mixtures are also common. Therefore, spills with compositions ranging from E10 to E95 can be anticipated. The compounds of main concern associated with gasoline spills are benzene, toluene, ethylbenzene and xylenes (BTEX), trimethylbenzenes (TMBs) and naphthalene, due to their higher mobility and potential risks to human health. Ethanol is thought to increase mobility of the NAPL, create higher hydrocarbon concentrations in groundwater due to cosolvency, and decrease the rate of gasoline hydrocarbon biodegradation, with consequent increase in the length of the dissolved plumes. The objective of this research was to improve the knowledge about ethanol fate in the subsurface and the impacts it might have on the fate of gasoline compounds. To investigate that, laboratory experiments and controlled field tests supported by numerical modeling were conducted. To evaluate the impact of ethanol on dissolved hydrocarbon plumes, data from a controlled field test were evaluated using a numerical model. The mass discharge of BTEX, TMB and naphthalene from three sources (E0, E10 and E95) emplaced below the water table was compared to simulation results obtained in the numerical model BIONAPL/3D. It was shown that if ethanol fuel mixtures get below the water table, ethanol is dissolved and travels downgradient fast, in a short slug. Mass discharge from the E0 and E10 sources had similar hydrocarbon decay rates, indicating that ethanol from E10 had no impact on hydrocarbon degradation. In contrast, the estimated hydrocarbon decay rates were significantly lower when the source was E95. The aquifer did not have enough oxygen to support the mass loss observed assuming complete mineralization. Assuming a heterogeneous distribution of hydraulic conductivity did little to overcome this discrepancy. A better match between the numerical model and the field data was obtained assuming partial degradation of hydrocarbons to intermediate compounds, with consequent less demand for oxygen. Besides depending on the concentration of ethanol in the groundwater, the impact of ethanol on hydrocarbon degradation appears to be highly dependent on the aquifer conditions, such as availability of electron acceptors and adaptation of the microbial community. Another concern related to ethanol biodegradation is formation of explosive levels of methane. In this study, methane δ13C from toluene and ethanol as substrates was evaluated in microcosm tests. It was shown that methane is enriched in δ13C when ethanol is the substrate. Ethanol derived methane δ13C is in the range of -20‰ to 30‰, while methane from gasoline is around -55‰. The different ranges of δ13C allow it to be used as a tool to identify methane’s origin. This tool was applied to seven ethanol-gasoline contaminated sites. Methane origin could be clearly distinguished in five of the seven sites, while in the other two sites methane appears to have been produced from both ethanol and gasoline. Both ethanol and gasoline were identified as the source of methane in hazardous concentrations. The behaviour of ethanol fuels in the unsaturated zone was evaluated in 2-dimensional (2-D) lab tests and in a controlled field test. In the 2-D lab tests, dyed gasoline and ethanol were injected in the unsaturated zone simulated in a transparent plexiglass box packed with glass beads. Tests were performed under both static conditions and with horizontal groundwater flow. It was confirmed that some ethanol can be retained in the unsaturated zone pore water. However, most of the ethanol went through the unsaturated zone and reached the pre-existing gasoline pool. Ethanol displaced the NAPL to deeper positions, and it was shown that for large ethanol releases much of the gasoline can be displaced to below the water table. The ethanol that reaches the capillary fringe was shown to travel downgradient rapidly at the top of the capillary fringe, while ethanol was also retained in the unsaturated zone. The behaviour of ethanol fuel spills was further evaluated in a controlled field test. 200L of E10 containing around 5% MTBE was released into the unsaturated zone. Groundwater concentrations of ethanol, MTBE, BTEX, TMB and naphthalene above and below the water table were monitored downgradient of the source in multilevel wells. Lab tests were performed to evaluate the applicability of these samplers for volatile organic compounds. It was shown that volatilization losses might be significant when bubbles formation in the sampling line could not be avoided. A method for losses estimation and correction of the concentrations was developed. Concentrations in the source zone were measured in soil samples. Despite the thin (35 cm) unsaturated zone at the site, most of the ethanol was retained in the unsaturated zone pore water, above the capillary fringe. Being in zones of low effective hydraulic conductivity, ethanol was not transported downgradient, and remained in the unsaturated zone for more than 100 days. Ethanol mass discharge was much lower than would be anticipated based solely on the ethanol fraction in the gasoline and on its solubility. Oscillations in the water table, particularly when a shallow position was maintained for prolonged periods, flushed some ethanol to zones with high water saturation, where horizontal transport occurred. The ethanol that reaches the saturated zone appears in the downgradient wells as a slug, with relatively low concentrations. No effect of ethanol on gasoline hydrocarbons was observed, a consequence of most of the ethanol being retained in the unsaturated zone. In summary, spills of ethanol fuels might have two different outcomes, depending on whether most of the ethanol is retained in the unsaturated zone or if most reaches the capillary fringe and the saturated zone. The relation between the ethanol volume spilled and the retention capacity of the unsaturated zone will control the spill behaviour. The volume of ethanol that can be retained in the unsaturated zone is a function of the volume of water that is contacted by the infiltrating NAPL. Therefore, the type of soil, heterogeneities, depth to the water table and area of the spill will be determinant factors. If a relatively large volume of ethanol reaches the capillary fringe, ethanol will travel rapidly in the groundwater possibly in high concentrations, potentially enhancing dissolved hydrocarbon plumes. However, when most of the ethanol is retained in the unsaturated zone, it will likely be detected downgradient only in low concentration, and in pulses spread in time. In this scenario, impact on hydrocarbon plumes will be minor.

The unsaturated polyester/silica hybrids have been synthesized via sol-gel process and characterized in an effort to obtain a transparent hybrid material in this study, with emphasis on the effects of silica precursors and coupling agents. Chemical properties, thermal properties, and morphology of the hybrids were investigated by Fourier-transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), and scanning electron microscopy (SEM). The results showed that silica particles can be dispersed homogeneously in the UP matrix; also, physical and chemical interactions at the interface between UP and silica can be enhanced by adding coupling agents into the system. From the thermal and chemical properties measurement, the decomposition temperature of UP backbone and the heat distortion temperature (HDT) of UP/Silica hybrid were higher than pure UP. Solvent-resistance of UP/Silica hybrid was also enhanced by adding coupling agents. A model illustrating the chemical and physical interaction at the interface due to the addition of coupling agents is proposed to explain the resulted obtained.

Oligomers of hard and soft segments of unsaturated polyesters (UP) were synthesized. They were blended in different ratios and cured with various amounts of styrene. Based on the criteria of tensile strength and strain, hard segment/soft segment (60/40 wt %) UPs containing 35 wt % and 45 wt % of extra amount of styrene were chosen for further studies. Inorganic-organic hybrid materials were prepared by incorporating tetraethoxysilane and poly(dimethylsiloxane) into the UP resins via the sol-gel process by changing the ratios of HCl/TEOS, H2O/TEOS, TEOS/PDMS and the reaction time. The specimens of these hybrid materials after curing were characterized using the tensile tester, rheometer, scanning electron microscope (SEM), 29Si-NMR and thermogravimeter. In the condition of HCl/TEOS molar ratio 0.07, H2O/TEOS molar ratio 4, TEOS/PDMS weight ratio 90/10 and the reaction time 3 hours, the results of 29Si-NMR, SEM and silicone mapping indicate that these silica gels with 3D network were well dispersed in the UP resins. These specimens had tensile strength of 512¡Ó16 kgf/cm2 and elongation of 11¡Ó4 % which are above the criteria of inhibitors. From the erosion testing, flame retardants was added unsaturated polyester and inorganic-organic hybrid materials that can help to resist heat flame, remain of a fire on the surface had the char forming.

We have successfully developed an efficient approach to 3,4-disubstituted £\,£]-unsaturated £_-lactams from glutarimide, and proved to be applicable for the synthesis of hydrocinchonine and hydrocinchonidine.