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研究生:張家瑋
研究生(外文):Chia-Wei Chang
論文名稱:高性能含磷高分子Benzoxazine及聚醯亞胺之合成與應用
論文名稱(外文):Synthesis and Characterization of High Performance Phosphorus-containing Polybenzoxazines and Polyimides.
指導教授:林慶炫
學位類別:碩士
校院名稱:國立中興大學
系所名稱:化學工程學系所
學門:工程學門
學類:化學工程學類
論文種類:學術論文
畢業學年度:96
語文別:英文
論文頁數:80
中文關鍵詞:聚醯亞胺難燃高玻璃轉移溫度氧代氮代苯并環己烷
外文關鍵詞:benzoxazinepolyimidephosphorusflame retardancyhigh Tg
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The reported includes Part A and Part B. Part A is about an aromatic triamine- based flame-retardant benzoxazine (3), which can’t be prepared by traditional one-step procedure, was successfully prepared by a three-step procedure. The structures of (3) and two intermediates (1-2), were confirmed by IR, high-resolution mass, 1H and 31P NMR spectra. (3) was copolymerized with commercial benzoxazines (F-a) and (P-d) to improve the thermal and flame retardant properties. The effects of (3) on the thermal properties, dynamic mechanical properties, thermal mechanical properties and flame retardancy of copolybenzoxazines were investigated.
Part B is about two novel phosphorus-functionalized aromatic diamines, 1,1-bis(4-aminodiphenyl)-1-(6-oxido-6H-dibenz <c,e> <1,2> oxaphosphorin-6-yl) ethane (1) and bis(4-aminodiphenyl)-(6-oxido-6H-dibenz <c,e> <1,2> oxaphosphorin -6-yl)-phenylmethane (2), were synthesized via a one-pot procedure. A SN1 mechanism was proposed for the preparation. A series of polyimides (5a-5d, 6a-6d) with bulky biphenylene phosphinate pendant were prepared from the condensation of (1-2) with various aromatic dianhydrides in DMAc, followed by thermal imidization. Polyimides (5a-5d) are flexible and creasable, and display high Tg (318-392 oC), high moduli (3.39-4.49 GPa), low coefficient of thermal expansion (42-50 ppm/ oC), and high thermal stability (5 wt% degradation temperatures at 426-439 oC). In contrast, polyimides (6a-6d) are brittle due to the rigid structure and two bulky substituents retard the mobility of the molecular chains.
Contents

Chapter 1 Aromatic Triamine-based Flame-Retardant Benzoxazine and Its High Performance Copolybenzoxazines.

1.1 Introduction 1
1.2 Experimental Section 2
1.2.1 Materials 2
1.2.2 Characterization 4
1.2.3 Syntheses of Monomer and Polymer (Scheme 1-1) 5
1.2.3.1 Preparation and characterization of (1). 5
1.2.3.2 Preparation and characterization of (2) 5
1.2.3.3 Preparation and characterization of (3). 6
1.2.3.4 Preparation of polybenzoxazines 6
1.3 Results and Discussion 6
1.3.1 Synthesis and characterization of monomers 6
1.3.2 Single-crystal data of (3) 11
1.3.3 DSC thermograms of benzoxazines 17
1.3.4 Curing of benzoxazines probed by IR 17
1.3.5 Thermal properties of polybenzoxazines 21
1.3.6 Thermal stability of polybenzoxazines. 21
1.3.7 Flame retardancy. 22
1.4 Conclusions 29
Reference. 30


Chapter 2 Facile Preparation of Phosphorus-functionalized Polyimides with Extremely High Tg

2.1 Introduction 32
2.2 Experimental 33
2.2.1 Materials. 33
2.2.1 Characterization. 34
2.2.2 Syntheses of Monomer and Polymer 35
2.2.2.1 1,1-bis(4-aminodiphenyl)-1-(6-oxido-6H -dibenz <c,e> <1,2> oxa- phosphorin-6-yl) ethane (1). 35
2.2.2.2 bis(4-aminodiphenyl)-(6-oxido-6H-dibenz <c,e> <1,2> oxaphosphorin -6-yl)-phenylmethane (2). 35
2.2.2.3 Preparation of Polyimides 37
2.3 Results and Discussion 38
2.3.1 Synthesis of (1) and (2). 38
2.3.2 Characterization of (1-2). 40
2.3.3 Polyimide Synthesis 54
2.3.4 Properties of the Polyimides 62
2.3.6.1 Organosolubility 62
2.3.6.2 Crystallinity 64
2.3.6.3 Film quality and thermal properties 65
2.3.6.4 Thermal Stability 70
1.5 Conclusions 73
Reference 74

Appendix 77
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