本實驗主要使用擁有兩個末端位置碳碳雙鍵之雙馬來醯亞胺(N,N'-bismaleimide-4,4'-Diphenylmethane, BMI) 與擁有CH2活性氫之1,3-雙甲基巴比妥酸 (1,3-Dimethylbarbituric acid, 13BTA) 和擁有兩個NH活性氫之5,5-雙甲基巴比妥酸(5,5-Dimethylbarbituric acid, 55BTA)進行聚合反應，並使用可促進麥克加成反應(Michael addition reaction)之觸媒以及可抑制自由基反應之抑制劑，將雙馬來醯亞胺與巴比妥酸內包含之兩種競爭反應麥克加成反應與自由基加成反應(Free radical reaction)各別進行其反應動力學研究。
主要使用微分式掃描熱量分析儀(DSC)，在各溫度下反應兩小時所獲得之放熱量，經數據處理與計算後選用最適合之反應動力學模型，再利用Arrhenius equation 計算出活化能(Ea)與頻率因子(A)；再利用核磁共振光譜儀(NMR)、膠體滲透分析儀(GPC)、熱重/熱示差分析儀(TGA)等儀器，分析並比較其反應性、耐熱性等性質。

This work studied the effects of catalysts on the kinetics of polymerization of N,N'-bismaleimide-4,4'-Diphenylmethane (BMI) with 1,3-Dimethylbarbituric acid (13BTA) or 5,5-Dimethylbarbituric acid (55BTA).The reaction between the two terminal -C=C- groups of BMI with 13BTA containing one CH2 group or 55BTA containing two NH groups were investigated. Addition of catalysts to promote Michael addition reaction and use of inhibitor hydroquinone (HQ) to inhibit free radical polymerization were also studied. In this manner, Michael addition polymerizations of BMI with 13BTA or 55BTA can be studied without the interference of free radical polymerization.
DSC was used to obtain the reaction kinetics data, then data were used to choose the best-fit kinetics model and determine triplet kinetics parameters. NMR, GPC and TGA were employed to study the reactivity of 13BTA and 55BTA.

[1] INSIDE共同編輯, 《第三台起火的Tesla》, 取自網址:
http://www.inside.com.tw/2013/11/11/i-would-buy-another-one-in-a-heartbeat
[2] J.-P. Pan, G.-Y. Shiau, S.-S. Lin, and K.-M. Chen, "Effect of Barbituric acid on the Self-Polymerization Reaction of Bismaleimides," Journal of Applied Polymer Science, vol. 45, pp. 103-109, 1992.
[3] C.-S. Chern, H.-L. Su, J.-M. Hsu, J.-P. Pan, and T.-H. Wang, " Understanding hyperbranched polymerization mechanisms," Society of Plastics Engineers, 2011.
[4] L. R. Dix, J. R. Ebdon, N. J. Flint, P. Hodge, and R. O'Dell, "Chain extension and crosslinking of telechelic oligomers—I. Michael additions of bisamines to bismaleimides and bis (acetylene ketone) s," European polymer journal, vol. 31, pp. 647-652, 1995.
[5] M. Sava and C. Grigoras, "Bismaleimide monomers and polymers with ester and ether units. Synthesis and properties," Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, vol. 42, pp. 1095-1108, 2005.
[6] Z. Shen, J. Schlup, and L. Fan, "Synthesis and characterization of leather impregnated with bismaleimide (BMI)–Jeffamine® resins," Journal of applied polymer science, vol. 69, pp. 1019-1027, 1998.
[7] E.D. Bergman, D. Ginsburg, R. Pappo, “The Michael reaction”, Organic Reaction, 1959.
[8] M. E. Jung, "Stabilized nucleophiles with electron deficient alkenes and alkynes," Comprehensive organic synthesis, vol. 4, p. 1, 1991.
[9] S. Tokura, S.-i. Nishimura, and N. Nishi, "Studies on chitin IX. Specific binding of calcium ions by carboxymethyl-chitin," Polymer journal, vol. 15, pp. 597-602, 1983.
[10] J. Pavlinec and N. Moszner, "Photocured polymer networks based on multifunctional β‐ketoesters and acrylates," Journal of applied polymer science, vol. 65, pp. 165-178, 1997.
[11] J. Crivello, D. Conlon, and S. Rice, "Bismaleimide-bisvinylether copolymers: A new class of thermosetting resins," Polymer Bulletin, vol. 13, pp. 409-415, 1985.
[12] I. M. Brown and T. C. Sandreczki, "Cross-linking reactions in maleimide and bis (maleimide) polymers. An ESR study," Macromolecules, vol. 23, pp. 94-100, 1990.
[13] L. G. Wade, Organic Chemistry 5th Ed. Mechanism supplements origina, 2002.
[14] N. Tsubokawa, N. Shibata, and Y. Sone, "Radical Polymerization of Methyl Methacrylate Initiated by an Enolizable Ketone-Carbon Black System," Journal of Polymer Science, vol. 21, pp. 425-433, 1983.
[15] H.-L. Su, J.-M. Hsu, J.-P. Pan, T.-H. Wang, F.-E. Yu, and C.-S. Chern, "Kinetic and structural studies of the polymerization of N,N′-bismaleimide-4,4′-diphenylmethane with barbituric acid," Polymer Engineering & Science, vol. 51, pp. 1188-1197, 2011.
[16] C. Gimbert, M. Lumbierres, C. Marchi, M. Moreno-Mañas, R. M. Sebastián, and A. Vallribera, "Michael additions catalyzed by phosphines. An overlooked synthetic method," Tetrahedron, vol. 61, pp. 8598-8605, 2005.
[17] B. D. Mather, K. Viswanathan, K. M. Miller, and T. E. Long, "Michael addition reactions in macromolecular design for emerging technologies," Progress in Polymer Science, vol. 31, pp. 487-531, 2006.
[18] L.-W. Xu and C.-G. Xia, "Highly efficient phosphine-catalyzed aza-Michael reactions of α,β-unsaturated compounds with carbamates in the presence of TMSCl," Tetrahedron Letters, vol. 45, pp. 4507-4510, 2004.
[19]Ajmal R. Bhat, Rupali S. Selokar, Jyotsna S. Meshram, and R. S. Dongre1, "Triethylamine: an efficient N-base catalyst for synthesis of annulated uracil derivativies in aqueous ethanol," JMESCN, pp. 1653-1657, 2014.
[20]S.Zhou, M.Xu, S.Ye, D.Li, J.Xu, P.Mao, J.Xiong, “Facile aza-Michael additions of uracil derivatives to acrylates”, JOURNAL OF CHEMICAL RESEARCH, pp. 114-117, 2012
[21] S. Vyazovkin, A. K. Burnham, J. M. Criado, L. A. Pérez-Maqueda, C. Popescu, and N. Sbirrazzuoli, "ICTAC Kinetics Committee recommendations for performing kinetic computations on thermal analysis data," Thermochimica Acta, vol. 520, pp. 1-19, 2011.
[22] A. Khawam and D. R. Flanagan, "Solid-State Kinetic Models: Basics and Mathematical Fundamentals," The Journal of Physical Chemistry B, pp. 17315-17328, 2006.
[23] T. Pascal, R. Mercier, and B. Sillion, "New semi-interpenetrating polymeric networks from linear polyimides and thermosetting bismaleimides. 1: Synthesis and characterization of starting components," Polymer, vol. 30, pp. 739-744, 1989.
[24] C. S. Wang and C. H. Lin, "Synthesis and properties of phosphorus containing copoly (bismaleimide)," Polymer, vol. 40, pp. 5665-5673, 1999.
[25] R. H. Pater, “Thermosetting Polyimides: A Review”, SAMPE J , 1994.
[26] P. Mison and B. Sillion, "Thermosetting oligomers containing maleimides and nadimides end-groups," in Progress in Polyimide Chemistry I, ed: Springer, pp. 137-179,1999.
[27] Z. D. Xiang and F. R. Jones, "Thermal degradation of an end-capped bismaleimide resin matrix (PMR-15) composite reinforced with pan-based carbon fibres," Composites science and technology, vol. 47, pp. 209-215, 1993.
[28] A. von. Baeyer, “Untersuchungen uber die Harsauregrouppe”, Ann. Chem. Pharm. Vol.127 , pp. 199, 1863.
[29] G. B. Kauffman, "Adolf von Baeyer and the Naming of Barbituric Acid," Journal of Chemical Education, vol. 57, 1980.
[30] K. T. Mahmudov, M. N. Kopylovich, A. M. Maharramov, M. M. Kurbanova, A. V. Gurbanov, and A. J. L. Pombeiro, "Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds," Coordination Chemistry Reviews, vol. 265, pp. 1-37, 2014.
[31] P. Pino, G. Braca, and G. Sbrana, "PREPARATION OF HYDROQUINONE," US Patent No.3355503, Nov.28, 1967.
[32]化工百科全書編輯委員會，《化工百科全書》，北京:化學工業出版社，pp351-368，1990
[33] 化學工業出版社組織，《中國化工產品大全》第三版，北京:化學工業出版社，p187，2005