3，3-二硝基-1-丁烯的合成及其聚合反应研究
|
摘要
高聚物粘结炸药(PBX)由主体炸药、粘结剂、增塑剂及辅助添加剂组成。在PBX配方中,粘结剂研究是核心和关键所在。偕二硝基类化合物具有含有中等能量,稳定性好等优点,在含能材料中有着广泛的应用。将偕二硝基化合物引入到高聚物粘结炸药中,将弥补惰性粘结剂造成的能量损失,对提高炸药的能量有所贡献。
本文设计合成了偕二硝基化合物3,3-二硝基-1-丁烯,并研究其均聚、共聚反应及与聚甲基氢硅氧烷进行的硅氢化反应。
本文以硝基乙烷为原料,经过硝化氧化反应、Michael加成、水解反应、Hunsdiecker反应及消除反应合成出3,3-二硝基-1-丁烯。不仅对原有的合成路线进行了改进,还具体讨论反应的原理及具体的反应过程。
探讨了以偶氮二异丁腈(AIBN)作为引发剂,3,3-二硝基-1-丁烯的均聚反应以及与丙烯腈的共聚反应。研究了单体发生聚合反应时的具体过程,讨论了反应温度、引发剂浓度、共聚中不同单体投料量之比对聚合反应的影响。分析了3,3-二硝基-1-丁烯自由基聚合反应失败的原因。
此外,研究了3,3-二硝基-1-丁烯与聚甲基氢硅氧烷进行硅氢化反应。通过对不同条件下实验结果的分析,进一步论证3,3-二硝基-1-丁烯自身结构对其反应活性的制约影响。
利用已经十分成熟的合成方法制备丙烯酸偕二硝基丙酯(DNPA)、α-甲基丙烯酸偕二硝基丙酯(DNPMA)两种偕二硝基化合物,并成功地与聚甲基氢硅氧烷发生硅氢化反应,制备出两种含偕二硝基的有机硅接枝聚合物。
使用傅立叶红外光谱(FT-IR),核磁共振氢谱(1H NMR),凝胶色谱(GPC),差热扫描量热仪(DSC)等分析手段对产物进行分析表征。
Plastic bonded explosive is composed of main expolsive, binders, plasticizers and other inert additives. The research on binders is the core in the formula of PBX. As compounds with gem-dinitro groups which own middle energy is stable, a large number of gem-dinitro compounds have been applied in energetic materials producting. The utilization of gem-dintro compounds as binders in polymer bonded exposive could increase the ernergy of PBX.
3,3-dinitro-1-butene was designed and synthesized in the present thesis. Meanwhile, the author studied the homopolymerization and copolymerization of 3,3-dinitro-1-butene, and the hydrosilylation between 3,3-dinitro-1-butene and Poly(methylhydrosiloxane) (PMHS).
3,3-dinitro-1-butene was synthesized through five steps which were nitration-oxidation, Meachel addition, hydrolyzation, Hunsdiecker reaction and elimination from nitroethane. The author ameliorated the old way of synthesization and discussed the reacted principle.
Homopolymerization of 3,3-dinitro-1-butene and its copolymerization with acrtlonitrile were carried out with azobisisobutyronireile(AIBN). The author studied the processes in polymerization and designed a number of reaction to estimate the infection like temperature, the concentration of AIBN, and so on. Finally, the unreactive reason of 3,3-dinitro-1-butene in polymerization was analyzed.
Besides, hydrosilylation of 3,3-dinitro-1-butene and PMHS was reacted. By analysis of experimental datas, the conclusion that the characteristic of monomer`s configuration was the primary restricted fator in reaction was confirmed.
Using the existing way to synthesize two monoers, such as 2,2-dinitropropyl acrtlate(DNPA) and 2,2-dinitropropyl methacrylate (DNPMA). The hydrosilylation between PMHS and these two compounds were synthesizd simply came ture and got two grafting compounds containing gem-dinitro.
The compounds were charactered by FT-IR, 1H NMR, GPC, DSC, and so on.
本文设计合成了偕二硝基化合物3,3-二硝基-1-丁烯,并研究其均聚、共聚反应及与聚甲基氢硅氧烷进行的硅氢化反应。
本文以硝基乙烷为原料,经过硝化氧化反应、Michael加成、水解反应、Hunsdiecker反应及消除反应合成出3,3-二硝基-1-丁烯。不仅对原有的合成路线进行了改进,还具体讨论反应的原理及具体的反应过程。
探讨了以偶氮二异丁腈(AIBN)作为引发剂,3,3-二硝基-1-丁烯的均聚反应以及与丙烯腈的共聚反应。研究了单体发生聚合反应时的具体过程,讨论了反应温度、引发剂浓度、共聚中不同单体投料量之比对聚合反应的影响。分析了3,3-二硝基-1-丁烯自由基聚合反应失败的原因。
此外,研究了3,3-二硝基-1-丁烯与聚甲基氢硅氧烷进行硅氢化反应。通过对不同条件下实验结果的分析,进一步论证3,3-二硝基-1-丁烯自身结构对其反应活性的制约影响。
利用已经十分成熟的合成方法制备丙烯酸偕二硝基丙酯(DNPA)、α-甲基丙烯酸偕二硝基丙酯(DNPMA)两种偕二硝基化合物,并成功地与聚甲基氢硅氧烷发生硅氢化反应,制备出两种含偕二硝基的有机硅接枝聚合物。
使用傅立叶红外光谱(FT-IR),核磁共振氢谱(1H NMR),凝胶色谱(GPC),差热扫描量热仪(DSC)等分析手段对产物进行分析表征。
Plastic bonded explosive is composed of main expolsive, binders, plasticizers and other inert additives. The research on binders is the core in the formula of PBX. As compounds with gem-dinitro groups which own middle energy is stable, a large number of gem-dinitro compounds have been applied in energetic materials producting. The utilization of gem-dintro compounds as binders in polymer bonded exposive could increase the ernergy of PBX.
3,3-dinitro-1-butene was designed and synthesized in the present thesis. Meanwhile, the author studied the homopolymerization and copolymerization of 3,3-dinitro-1-butene, and the hydrosilylation between 3,3-dinitro-1-butene and Poly(methylhydrosiloxane) (PMHS).
3,3-dinitro-1-butene was synthesized through five steps which were nitration-oxidation, Meachel addition, hydrolyzation, Hunsdiecker reaction and elimination from nitroethane. The author ameliorated the old way of synthesization and discussed the reacted principle.
Homopolymerization of 3,3-dinitro-1-butene and its copolymerization with acrtlonitrile were carried out with azobisisobutyronireile(AIBN). The author studied the processes in polymerization and designed a number of reaction to estimate the infection like temperature, the concentration of AIBN, and so on. Finally, the unreactive reason of 3,3-dinitro-1-butene in polymerization was analyzed.
Besides, hydrosilylation of 3,3-dinitro-1-butene and PMHS was reacted. By analysis of experimental datas, the conclusion that the characteristic of monomer`s configuration was the primary restricted fator in reaction was confirmed.
Using the existing way to synthesize two monoers, such as 2,2-dinitropropyl acrtlate(DNPA) and 2,2-dinitropropyl methacrylate (DNPMA). The hydrosilylation between PMHS and these two compounds were synthesizd simply came ture and got two grafting compounds containing gem-dinitro.
The compounds were charactered by FT-IR, 1H NMR, GPC, DSC, and so on.
引文
[1] 孙业斌, 惠君明编. 军用混合炸药[M]. 北京:兵器工业出版社, 1995: 175-213
[2] 王金英, 柴涛,张景林等. PBX 传爆药撞击感度影响因素的研究[J]. 华北工学院学报, 2004, 25(4): 289-292
[3] 王文俊. 新型含能材料及其推进剂的研究进展[J]. 推进技术, 2001, 22(4): 269-275
[4] Frankel M B, Grant L R, Flanagan J E, et al. Historical development of GAP[R]. AIAA, 1989, 89-2307
[5] 沙恒. 国外双氮甲基氧杂丁环的应用研究[J]. 固体火箭技术, 1998, 1, 39-42
[6] 庞维强, 张教强, 国际英等. 21 世纪国外固体推进剂的研究与发展趋势[J]. 化学推进剂与高分子材料, 2005, 3(3): 16-19
[7] Kazushige K, Kobayashi K, Frankel, et al. Mechanical properties of GAP reduced smoke propellants [R]. AIAA, 1996, 96-3253
[8] Milton B F, Tarzana, Joseph E F, et al. Energetic hydroxyl-terminated azide polymer [P]. US 4268450, 1981
[9] Frankel M B. Aqueous process for quantitative conversion of polyepichlorohydrin to GAP[P]. US 379894, 1983
[10] Elie A. Branched hydroxyl azido polymer[C]. ICT21st, 1990
[11] 施明达. GAP 与 GAP 推进剂的研究进展[J]. 火炸药, 1994, 3(1): 9-15
[12] 杜磊, 姜志荣. 国外固体推进剂含能黏合剂的新进展[J]. 推进技术, 1994, 4, 67-76
[13] 张君启, 张炜等. 固体推进剂用含能黏合剂体系研究进展[J]. 化学推进剂与高分子材料, 2006, 4(3): 6-9
[14] Reed, May L C. High nitrogen smoke composition[P]. US 5061329, 1991
[15] Tokui H. New energetic molecules and there applications in energetid materials[C]. 21 st Int Ann Conf of ICT, 1990, 7, 1-14
[16] 沙恒, 杨红梅. 新型含能粘结剂 BAMO[J]. 火炸药, 1995, 4, 34-36
[17] 施明达. 一种新型含能材料——叠氮有机化合物[J]. 火炸药, 1992, 4, 24-30
[18] Wen Hsin H. J. Propulsion. 1991, 7(4): 497-504
[19] 御手洗善昭. AMMO 系ポリマーの 物理化学性能[J]. 工业火药, 1990, 151(4): 240-244
[20] 卢先明, 甘孝贤. 3,3-双叠氮甲基氧丁环及其均聚物的合成与性能[J]. 火炸药学报, 2004, 27(3): 49-52
[21] 李娜, 甘孝贤. 3-叠氮甲基-3-甲基氧丁环的合成[J]. 火炸药学报, 2005, 28(3): 57-5
[22] 王文俊, 张占权. 21 世纪初固体推进剂技术展望[J]. 推进技术, 2000, 21(6): 1-5
[23] 胡中波, 甘孝贤. 以取代氧丁环为母体制备含能粘合剂[J]. 含能材料, 2004, 12(1): 62-64
[24] 徐武, 王煊军, 刘祥萱等. 含能粘合剂研究的新进展[J]. 火箭推进, 2007, 33(2): 44-47
[25] Beaupre F, Ampleman G, Ahad E. Application of GAP-based binders to low vulnerability gun propellant formulations[A]. 6th International Gun Propellant& Propulsion Symposium[C], 1994
[26] Beaupre F, Ahad E. Preliminary studies of HELOVA-type gun propellant formulations containing energetic binders[A]. International Symposium Energetic Materials Technology[C], 1994
[27] Ampleman G, Beaupre F. Synthesis of linear GAP-based energetic thermoplastic elastomers for use in HELOVA gun propellant formulations[A]. 27th International ICT Conference[C], 1996
[28] Beaupre F, Ampleman G. Processing and evaluation of gun propellant formulations containing energetic thermoplastic elastomers[A]. NDIA IM/EM Symposium [C], 1998
[29] Ampleman G, Marois A, Beaupre F. Synthesis of energetic copolyurethane thermo- plastic elastomers for recyclable GAP-based HELOVA gun properllants [A]. NAIA IM/EM Symposium[C], 1998
[30] 何利明, 肖忠良, 张续柱等. 国外火药含能粘结剂研究动态[J]. 含能材料, 2003, 11(2): 99-102
[31] Peters S T, Meschberger J A, Costin R. Correlation of binder properties to propellant properties[C]. 21 st Int Ann Conf of ICT, 1990: 26
[32] Kaste P J. Characterization of pommercial TPE for LOVA propellant[C]. Ibid, 1990: 44
[33] Manser G E. The development of energetic oxetane polymers[C]. Ibid, 1990: 50
[34] 韩国国防发展局. Development of the copolymer of dinitropropyl and dinitrobutyl acrylates for pressable PBX formulations[C]. Insensitive Munitions and Energetic Materials Technology Symposium, 2001: 163-169
[35] Vasile C, Seymour B. Handbook of Polyolefins[M]. Marcel Dekker, 1993
[36] 王志平, 陈颖. 烯烃类聚合物的改性[J]. 中国塑料, 1999, 13(11): 10-17
[37] 胡友良, 陈商涛. 烯烃的共聚合反应及聚烯烃改性:Ⅰ.烯烃与极性单体的共聚合[J]. 石化技术与应用, 2004, 22(1): 1-3
[38] 晨光化工研究所有机硅编写组编著. 有机硅单体及其聚合物[M]. 北京:化学工业出版社, 1986
[39] 吴森纪编著. 有机硅及其应用[M]. 北京:科学技术文献出版社, 1990
[40] 幸松民,王一璐编著. 有机硅合成工艺及产品应用[M]. 北京:化学工业出版社, 2000
[41] Harold S, Lawrence Z. The condensation of 1,1-dinitroethane with electronegatively substituted unsaturated compounds. The synthesis of 3,3-dinitro-1-butene [J]. J.Am.Chem.Soc., 1951, 73(3): 1276-1278
[42] Ralph B K, Harold S. A new general reaction for preparing gem-dintiro compounds: oxidative nitration[J]. J.Am.Chem.Soc., 1961, 83(16): 3535-3536
[43] Hagit S, Amir W, Yehiel K, et al. Synehesis of 2,2-dinitrobutanol. 34th[C]. International Annual Conference of ICT, 140, 1-9
[44] Edward E H, John S D , Love A, et al. Synthesis of 2,2-dinitropropanol[J]. I&EC product research and development, 1962, 1(2):108-115
[45] Grakauskas V, Garver L C, Baum K. Synthesis of geminal dinitro compounds[P]. US:4910322, 1990
[46] Lee C G, Grakauskas V, Kurt B. Catalyzed oxidative nitration of nitronate salts[J]. J.Org.Chem., 1985, 50(10):1699-1702
[47] 江希华. 从废的氯化银中回收银[J]. 苏盐科技, 1999, 3, 14
[48] 熊道陵, 罗序燕等. 从废感光材料中制备硝酸银的新方法[J]. 化工进展, 2004, 23(12): 1338-1441
[49] 余建国. 由废定影液--卤化银制备硝酸银[J]. 化学世界, 1995, 5, 491-492
[50] 卢江, 梁晖. 高分子化学[M]. 北京: 化学工业出版社,2005: 66-67
[51] 顾雪蓉, 陆云. 高分子科学基础[M]. 北京:化学工业出版社, 2003: 145
[52] 复旦大学高分子科学系编著. 高分子化学[M]. 复旦大学出版社, 1995: 100
[53] 卢江, 梁晖. 高分子化学[M]. 北京: 化学工业出版社,2005: 146-147
[54] Sommer L H, Pieurtsza E W, Whimtore F C. Peroxide catalyzeddadition of trichlorosilnae tol-oeetne[J]. J.Am.Chem.Soc., 1947, 69(l):188
[55] 黄光佛, 卿胜波等. 硅氢加成反应在聚合物制备及改性中的应用[J]. 有机硅材料, 2000, 14 (5): 23-26
[56] 师彤, 谢择民, 王清正. 含氢硅氧烷的硅氢加成反应[J]. 应用化学, 1995, 12(2): 113-114
[57] 赵培真, 王洪涛, 阚成友. 硅氢加成反应催化剂[J]. 有机硅材料及应用, 1995, 1, 1-5
[58] Gilkey J W, Hook D E. The Reaction of Olefins and Chlorohydrosilanes[J]. J.Am.Chem.Soc., 1947, 69(l): 2916
[59] Speier J L, Webster J A, Bmaes G H. The addtion of silicon hydrides to olefinie doublebonds, partⅡ.The use of gorupⅢ metal catalysts[J]. J.Am.Chem.Soc., 1957, 79(4):57
[60] Peortv A D. Ivzest Akda Nuak USSR. Odtel Khlm Nuak, 1958: 953
[61] 萧斌, 李凤仪, 戴延凤. 硅氢加成反应催化剂研究进展[J]. 化工新型材料, 2005, 33(10): 49-54
[62] 李光亮编著. 有机硅高分子化学[M]. 北京:科学出版社 1998: 28
[63] Bao-Yan Z, Jian-She H, Ying-Gang J, et al. Side-chain cholesteric liquid crystalline elastomers derived from nematic bis-olefinic crosslingking units[J]. Macromol. Chem. Phys, 2003, 204, 2123-2129
[64] 葛树琴, 刘红波, 任亚林. 聚硅氧烷侧链液晶高分子的合成与表征[J]. 合成化学, 2001, 9(4): 334-336
[65] Chain-Shu H, Li-Jen S, Ging-Ho H. Synthesis of liquid crystalline polysiloxanes and polymethacrylates with broad temperature ranges of the chiral smectic C phase[J]. Macromolecules, 1993, 26, 3161-3167
[66] 宋秘钊, 张廷有, 张慧君. 甲基丙烯酸酯_含氢聚硅氧烷接枝物的合成与表征[J]. 化学研究与应用, 2003, 15(6): 879-880
[67] 王大伟, 杨青芳, 张楠楠等. 甲基丙烯酸正丁酯_含氢硅油的合成与表征[J]. 中国胶黏剂, 2006, 15(10): 5-7
[68] Jürgen P, Veera B S, Lothar J, et al. Crosslinkable coupling agents: Synthesis and use for modification of interfaces in polymer blends[J]. Polymer, 2005, 46, 6563-6574
[69] Jerome M., Rosen, James R., et al. Heats of transition and fusion of nireoalkane alcohols and related nitroalkanes[J]. Molecular crystals liquid crystals, 1969, 6, 205-210
[70] Kunhhro T., Satsuki ABE., Keiho NAMBA. The polymerization and copolymerization of nitroalkyl acrylates and nitroalkyl methacrylates[J]. Journal of applied polymer science, 1968, 12, 1683-1695
[71] Harold S, Dean L L, Lawrence Z. Addition reactions of nitroalkanes with acrolein and methyl vinyl ketone. Selective reduction of nitrocarbonyl compounds to nitrocarbi- nols[J]. J.Am.Chem.Soc., 1952, 74, 3664-3668
[72] Henry R, Thomas J K. Selectinv redution of aliphatic nitroesters with lithium aluminum hydride[J]. J.Am.Chem.Soc., 1955, 77, 5740
[73] Herbert C B, Subba Rao B C. A new powerful reducting agent-sodium borohydride in the presence of aluminum chloride and other polyvalent metal halides[J]. J.Am.Chem.Soc., 1956, 78, 2582-2588
[2] 王金英, 柴涛,张景林等. PBX 传爆药撞击感度影响因素的研究[J]. 华北工学院学报, 2004, 25(4): 289-292
[3] 王文俊. 新型含能材料及其推进剂的研究进展[J]. 推进技术, 2001, 22(4): 269-275
[4] Frankel M B, Grant L R, Flanagan J E, et al. Historical development of GAP[R]. AIAA, 1989, 89-2307
[5] 沙恒. 国外双氮甲基氧杂丁环的应用研究[J]. 固体火箭技术, 1998, 1, 39-42
[6] 庞维强, 张教强, 国际英等. 21 世纪国外固体推进剂的研究与发展趋势[J]. 化学推进剂与高分子材料, 2005, 3(3): 16-19
[7] Kazushige K, Kobayashi K, Frankel, et al. Mechanical properties of GAP reduced smoke propellants [R]. AIAA, 1996, 96-3253
[8] Milton B F, Tarzana, Joseph E F, et al. Energetic hydroxyl-terminated azide polymer [P]. US 4268450, 1981
[9] Frankel M B. Aqueous process for quantitative conversion of polyepichlorohydrin to GAP[P]. US 379894, 1983
[10] Elie A. Branched hydroxyl azido polymer[C]. ICT21st, 1990
[11] 施明达. GAP 与 GAP 推进剂的研究进展[J]. 火炸药, 1994, 3(1): 9-15
[12] 杜磊, 姜志荣. 国外固体推进剂含能黏合剂的新进展[J]. 推进技术, 1994, 4, 67-76
[13] 张君启, 张炜等. 固体推进剂用含能黏合剂体系研究进展[J]. 化学推进剂与高分子材料, 2006, 4(3): 6-9
[14] Reed, May L C. High nitrogen smoke composition[P]. US 5061329, 1991
[15] Tokui H. New energetic molecules and there applications in energetid materials[C]. 21 st Int Ann Conf of ICT, 1990, 7, 1-14
[16] 沙恒, 杨红梅. 新型含能粘结剂 BAMO[J]. 火炸药, 1995, 4, 34-36
[17] 施明达. 一种新型含能材料——叠氮有机化合物[J]. 火炸药, 1992, 4, 24-30
[18] Wen Hsin H. J. Propulsion. 1991, 7(4): 497-504
[19] 御手洗善昭. AMMO 系ポリマーの 物理化学性能[J]. 工业火药, 1990, 151(4): 240-244
[20] 卢先明, 甘孝贤. 3,3-双叠氮甲基氧丁环及其均聚物的合成与性能[J]. 火炸药学报, 2004, 27(3): 49-52
[21] 李娜, 甘孝贤. 3-叠氮甲基-3-甲基氧丁环的合成[J]. 火炸药学报, 2005, 28(3): 57-5
[22] 王文俊, 张占权. 21 世纪初固体推进剂技术展望[J]. 推进技术, 2000, 21(6): 1-5
[23] 胡中波, 甘孝贤. 以取代氧丁环为母体制备含能粘合剂[J]. 含能材料, 2004, 12(1): 62-64
[24] 徐武, 王煊军, 刘祥萱等. 含能粘合剂研究的新进展[J]. 火箭推进, 2007, 33(2): 44-47
[25] Beaupre F, Ampleman G, Ahad E. Application of GAP-based binders to low vulnerability gun propellant formulations[A]. 6th International Gun Propellant& Propulsion Symposium[C], 1994
[26] Beaupre F, Ahad E. Preliminary studies of HELOVA-type gun propellant formulations containing energetic binders[A]. International Symposium Energetic Materials Technology[C], 1994
[27] Ampleman G, Beaupre F. Synthesis of linear GAP-based energetic thermoplastic elastomers for use in HELOVA gun propellant formulations[A]. 27th International ICT Conference[C], 1996
[28] Beaupre F, Ampleman G. Processing and evaluation of gun propellant formulations containing energetic thermoplastic elastomers[A]. NDIA IM/EM Symposium [C], 1998
[29] Ampleman G, Marois A, Beaupre F. Synthesis of energetic copolyurethane thermo- plastic elastomers for recyclable GAP-based HELOVA gun properllants [A]. NAIA IM/EM Symposium[C], 1998
[30] 何利明, 肖忠良, 张续柱等. 国外火药含能粘结剂研究动态[J]. 含能材料, 2003, 11(2): 99-102
[31] Peters S T, Meschberger J A, Costin R. Correlation of binder properties to propellant properties[C]. 21 st Int Ann Conf of ICT, 1990: 26
[32] Kaste P J. Characterization of pommercial TPE for LOVA propellant[C]. Ibid, 1990: 44
[33] Manser G E. The development of energetic oxetane polymers[C]. Ibid, 1990: 50
[34] 韩国国防发展局. Development of the copolymer of dinitropropyl and dinitrobutyl acrylates for pressable PBX formulations[C]. Insensitive Munitions and Energetic Materials Technology Symposium, 2001: 163-169
[35] Vasile C, Seymour B. Handbook of Polyolefins[M]. Marcel Dekker, 1993
[36] 王志平, 陈颖. 烯烃类聚合物的改性[J]. 中国塑料, 1999, 13(11): 10-17
[37] 胡友良, 陈商涛. 烯烃的共聚合反应及聚烯烃改性:Ⅰ.烯烃与极性单体的共聚合[J]. 石化技术与应用, 2004, 22(1): 1-3
[38] 晨光化工研究所有机硅编写组编著. 有机硅单体及其聚合物[M]. 北京:化学工业出版社, 1986
[39] 吴森纪编著. 有机硅及其应用[M]. 北京:科学技术文献出版社, 1990
[40] 幸松民,王一璐编著. 有机硅合成工艺及产品应用[M]. 北京:化学工业出版社, 2000
[41] Harold S, Lawrence Z. The condensation of 1,1-dinitroethane with electronegatively substituted unsaturated compounds. The synthesis of 3,3-dinitro-1-butene [J]. J.Am.Chem.Soc., 1951, 73(3): 1276-1278
[42] Ralph B K, Harold S. A new general reaction for preparing gem-dintiro compounds: oxidative nitration[J]. J.Am.Chem.Soc., 1961, 83(16): 3535-3536
[43] Hagit S, Amir W, Yehiel K, et al. Synehesis of 2,2-dinitrobutanol. 34th[C]. International Annual Conference of ICT, 140, 1-9
[44] Edward E H, John S D , Love A, et al. Synthesis of 2,2-dinitropropanol[J]. I&EC product research and development, 1962, 1(2):108-115
[45] Grakauskas V, Garver L C, Baum K. Synthesis of geminal dinitro compounds[P]. US:4910322, 1990
[46] Lee C G, Grakauskas V, Kurt B. Catalyzed oxidative nitration of nitronate salts[J]. J.Org.Chem., 1985, 50(10):1699-1702
[47] 江希华. 从废的氯化银中回收银[J]. 苏盐科技, 1999, 3, 14
[48] 熊道陵, 罗序燕等. 从废感光材料中制备硝酸银的新方法[J]. 化工进展, 2004, 23(12): 1338-1441
[49] 余建国. 由废定影液--卤化银制备硝酸银[J]. 化学世界, 1995, 5, 491-492
[50] 卢江, 梁晖. 高分子化学[M]. 北京: 化学工业出版社,2005: 66-67
[51] 顾雪蓉, 陆云. 高分子科学基础[M]. 北京:化学工业出版社, 2003: 145
[52] 复旦大学高分子科学系编著. 高分子化学[M]. 复旦大学出版社, 1995: 100
[53] 卢江, 梁晖. 高分子化学[M]. 北京: 化学工业出版社,2005: 146-147
[54] Sommer L H, Pieurtsza E W, Whimtore F C. Peroxide catalyzeddadition of trichlorosilnae tol-oeetne[J]. J.Am.Chem.Soc., 1947, 69(l):188
[55] 黄光佛, 卿胜波等. 硅氢加成反应在聚合物制备及改性中的应用[J]. 有机硅材料, 2000, 14 (5): 23-26
[56] 师彤, 谢择民, 王清正. 含氢硅氧烷的硅氢加成反应[J]. 应用化学, 1995, 12(2): 113-114
[57] 赵培真, 王洪涛, 阚成友. 硅氢加成反应催化剂[J]. 有机硅材料及应用, 1995, 1, 1-5
[58] Gilkey J W, Hook D E. The Reaction of Olefins and Chlorohydrosilanes[J]. J.Am.Chem.Soc., 1947, 69(l): 2916
[59] Speier J L, Webster J A, Bmaes G H. The addtion of silicon hydrides to olefinie doublebonds, partⅡ.The use of gorupⅢ metal catalysts[J]. J.Am.Chem.Soc., 1957, 79(4):57
[60] Peortv A D. Ivzest Akda Nuak USSR. Odtel Khlm Nuak, 1958: 953
[61] 萧斌, 李凤仪, 戴延凤. 硅氢加成反应催化剂研究进展[J]. 化工新型材料, 2005, 33(10): 49-54
[62] 李光亮编著. 有机硅高分子化学[M]. 北京:科学出版社 1998: 28
[63] Bao-Yan Z, Jian-She H, Ying-Gang J, et al. Side-chain cholesteric liquid crystalline elastomers derived from nematic bis-olefinic crosslingking units[J]. Macromol. Chem. Phys, 2003, 204, 2123-2129
[64] 葛树琴, 刘红波, 任亚林. 聚硅氧烷侧链液晶高分子的合成与表征[J]. 合成化学, 2001, 9(4): 334-336
[65] Chain-Shu H, Li-Jen S, Ging-Ho H. Synthesis of liquid crystalline polysiloxanes and polymethacrylates with broad temperature ranges of the chiral smectic C phase[J]. Macromolecules, 1993, 26, 3161-3167
[66] 宋秘钊, 张廷有, 张慧君. 甲基丙烯酸酯_含氢聚硅氧烷接枝物的合成与表征[J]. 化学研究与应用, 2003, 15(6): 879-880
[67] 王大伟, 杨青芳, 张楠楠等. 甲基丙烯酸正丁酯_含氢硅油的合成与表征[J]. 中国胶黏剂, 2006, 15(10): 5-7
[68] Jürgen P, Veera B S, Lothar J, et al. Crosslinkable coupling agents: Synthesis and use for modification of interfaces in polymer blends[J]. Polymer, 2005, 46, 6563-6574
[69] Jerome M., Rosen, James R., et al. Heats of transition and fusion of nireoalkane alcohols and related nitroalkanes[J]. Molecular crystals liquid crystals, 1969, 6, 205-210
[70] Kunhhro T., Satsuki ABE., Keiho NAMBA. The polymerization and copolymerization of nitroalkyl acrylates and nitroalkyl methacrylates[J]. Journal of applied polymer science, 1968, 12, 1683-1695
[71] Harold S, Dean L L, Lawrence Z. Addition reactions of nitroalkanes with acrolein and methyl vinyl ketone. Selective reduction of nitrocarbonyl compounds to nitrocarbi- nols[J]. J.Am.Chem.Soc., 1952, 74, 3664-3668
[72] Henry R, Thomas J K. Selectinv redution of aliphatic nitroesters with lithium aluminum hydride[J]. J.Am.Chem.Soc., 1955, 77, 5740
[73] Herbert C B, Subba Rao B C. A new powerful reducting agent-sodium borohydride in the presence of aluminum chloride and other polyvalent metal halides[J]. J.Am.Chem.Soc., 1956, 78, 2582-2588