主链型偶氮聚合物的制备、结构和性能研究
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摘要
偶氮聚合物既具有偶氮基团的光学活性，又具有高分子材料优异的力学性能和加工性能，因此在光信息存储材料、非线性光学材料、液晶材料、生物分子活性光调控、纳米材料等领域具有重要的应用价值。本文在分析有关偶氮化合物的合成、偶氮聚合物的合成、研究和应用资料的基础上，针对主链型偶氮聚合物在光机械效应、光生物活性调控及光致变色材料等方面的应用，系统的研究了偶氮聚酰胺、偶氮聚氨基脲、含偶氮基团聚碳酸酯的制备工艺、结构及性能。获得了以下的研究成果：
(1) 以对硝基苯甲酸，间硝基苯甲酸、2-氯-4-硝基苯甲酸和3-甲基-4-硝基苯甲酸为原料，葡萄糖作还原剂，氯化亚砜作酰化剂，合成了偶氮苯-4，4’-二甲酰氯、偶氮苯-3，3’-二甲酰氯、3，3’-二氯-偶氮苯-4，4’-二甲酰氯和2，2’-二甲基-偶氮苯-4，4-二甲酰氯；以间硝基苯甲酰肼为原料，硼氢化钠为还原剂，合成了3，3’-偶氮苯二甲酰肼。
(2) 用红外光谱、~1HNMR和元素分析对偶氮苯二甲酰氯和3，3’-偶氮苯二甲酰肼的结构进行了表征。2，2’-二甲基-偶氮苯-4，4’-二甲酰氯和3，3’-偶氮苯二甲酰肼未见文献报道。
(3) 以4，4’-双(4-氨基苯氧基)二苯砜和偶氮苯二甲酰氯为原料，通过低温溶液缩聚合成了四种含醚键砜基偶氮聚酰胺。优化了聚合工艺条件，偶氮聚酰胺的特性粘度在0.82～1.12(dl．g~(-1))之间。
(4) 用红外光谱、~1HNMR和元素分析表征了含醚键砜基偶氮聚酰胺的结构。结果表明，醚基和砜基的引入提高了聚合物在有机溶剂中的溶解性。TGA和DSC数据说明了合成的偶氮聚酰胺具有较高的热稳定性。用UV-Vis光谱表征了聚2，2’-二甲基-偶氮苯-4，4’-二甲酰4，4’-双(4-氨基苯氧基)二苯砜(PMPAB-BAPS)在N，N-二甲基乙酰胺(DMAc)中的光致变色性能。在365nm紫外光照下，聚合物发生了从反式-顺式的光异构化转变，25min达到平衡状态；25℃避光保存，PMPAB-BAPS又发生了顺式-反式的回归异构化反应，经过65h，完全恢复。升高温度，热回复异构化反应加快。
(5) 以2-三氟甲基-4，4’-二胺基二苯甲醚和偶氮苯-4，4’-二甲酰氯、偶氮苯-3，3’-二甲酰氯、3，3’-二氯-偶氮苯-4，4’-二甲酰氯、2，2’-二甲基-偶氮苯-4，4-二甲酰氯为原料，通过低温溶液缩聚合成了四种含三氟甲基的偶氮聚酰胺。偶氮聚酰胺
Azo polymers have not only optical activity of azobenzene ,but also good processability and mechanical properties of polymers. They are widely used in many fields such as, optical information storage materials, nonlinear optical materials, liquid crystal materials, light adjust and control materials of biological activity and nanophase materials. The developing trend of synthesis and application of azo compounds and polymers has been reviewed in this paper. Study on main-chain azo polymers was investigated in optical information storage materials, light adjust and control materials of biological activity, photochromism materials .The synthetic technique, structure and properties of main-chain azo polyamides , main-chain azo polyacylsemicarbazides and polycarbonate with azobenzene(PC-Azo) were studied systemically. The main results obtained can be summarized as follow:
(1) Using p-nitrobenzoic acid , m-nitrobenzoic acid, 3-methyl-4-nitrobenzoic acid, 2-chloro-4-nitrobenzoic acid as materials , glucose as reductant and thionyl chloride as acylating agent, four azobenzene -dicarbonylic chlorides were synthesized. Using sodium borohydride as reductant and dimethyl sulfoxide as solvent, 3,3'-azobis(benzoylhydrazide) was synthesized from m-nitrobenzoylhydrazide via reduction.
(2) The structures of four azobenzene-dicarbonylic chlorides and 3,3'-azobis(benzoylhydrazide) were confirmed by IR, ~1HNMR and elemental analysis. 3,3'-dimethy-azobenzene-4,4'-dicarbonylchloride and 3,3'-azobis(benzoylhydrazide) were synthesized in the first time.
(3) Four main-chain azo polyamides containing ether and sulfone group were synthesized from bis[4-(4-aminophenoxy)phenyl sulfone] and four azobenzene -dicarbonylic chlorides by low-temperature-solution condensation polymerization. The optimum conditions of condensation polymerization were obtained. Inherent Viscosity of four main-chain azo polyamides containing ether and sulfone group is from 0.82-1.12(dl.g~(-1)).
(4) The structures of four main-chain azo polyamides containing ether and sulfone group were confirmed by IR, ~1HNMR and elemental analysis. Incorporation
(1) 以对硝基苯甲酸，间硝基苯甲酸、2-氯-4-硝基苯甲酸和3-甲基-4-硝基苯甲酸为原料，葡萄糖作还原剂，氯化亚砜作酰化剂，合成了偶氮苯-4，4’-二甲酰氯、偶氮苯-3，3’-二甲酰氯、3，3’-二氯-偶氮苯-4，4’-二甲酰氯和2，2’-二甲基-偶氮苯-4，4-二甲酰氯；以间硝基苯甲酰肼为原料，硼氢化钠为还原剂，合成了3，3’-偶氮苯二甲酰肼。
(2) 用红外光谱、~1HNMR和元素分析对偶氮苯二甲酰氯和3，3’-偶氮苯二甲酰肼的结构进行了表征。2，2’-二甲基-偶氮苯-4，4’-二甲酰氯和3，3’-偶氮苯二甲酰肼未见文献报道。
(3) 以4，4’-双(4-氨基苯氧基)二苯砜和偶氮苯二甲酰氯为原料，通过低温溶液缩聚合成了四种含醚键砜基偶氮聚酰胺。优化了聚合工艺条件，偶氮聚酰胺的特性粘度在0.82～1.12(dl．g~(-1))之间。
(4) 用红外光谱、~1HNMR和元素分析表征了含醚键砜基偶氮聚酰胺的结构。结果表明，醚基和砜基的引入提高了聚合物在有机溶剂中的溶解性。TGA和DSC数据说明了合成的偶氮聚酰胺具有较高的热稳定性。用UV-Vis光谱表征了聚2，2’-二甲基-偶氮苯-4，4’-二甲酰4，4’-双(4-氨基苯氧基)二苯砜(PMPAB-BAPS)在N，N-二甲基乙酰胺(DMAc)中的光致变色性能。在365nm紫外光照下，聚合物发生了从反式-顺式的光异构化转变，25min达到平衡状态；25℃避光保存，PMPAB-BAPS又发生了顺式-反式的回归异构化反应，经过65h，完全恢复。升高温度，热回复异构化反应加快。
(5) 以2-三氟甲基-4，4’-二胺基二苯甲醚和偶氮苯-4，4’-二甲酰氯、偶氮苯-3，3’-二甲酰氯、3，3’-二氯-偶氮苯-4，4’-二甲酰氯、2，2’-二甲基-偶氮苯-4，4-二甲酰氯为原料，通过低温溶液缩聚合成了四种含三氟甲基的偶氮聚酰胺。偶氮聚酰胺
Azo polymers have not only optical activity of azobenzene ,but also good processability and mechanical properties of polymers. They are widely used in many fields such as, optical information storage materials, nonlinear optical materials, liquid crystal materials, light adjust and control materials of biological activity and nanophase materials. The developing trend of synthesis and application of azo compounds and polymers has been reviewed in this paper. Study on main-chain azo polymers was investigated in optical information storage materials, light adjust and control materials of biological activity, photochromism materials .The synthetic technique, structure and properties of main-chain azo polyamides , main-chain azo polyacylsemicarbazides and polycarbonate with azobenzene(PC-Azo) were studied systemically. The main results obtained can be summarized as follow:
(1) Using p-nitrobenzoic acid , m-nitrobenzoic acid, 3-methyl-4-nitrobenzoic acid, 2-chloro-4-nitrobenzoic acid as materials , glucose as reductant and thionyl chloride as acylating agent, four azobenzene -dicarbonylic chlorides were synthesized. Using sodium borohydride as reductant and dimethyl sulfoxide as solvent, 3,3'-azobis(benzoylhydrazide) was synthesized from m-nitrobenzoylhydrazide via reduction.
(2) The structures of four azobenzene-dicarbonylic chlorides and 3,3'-azobis(benzoylhydrazide) were confirmed by IR, ~1HNMR and elemental analysis. 3,3'-dimethy-azobenzene-4,4'-dicarbonylchloride and 3,3'-azobis(benzoylhydrazide) were synthesized in the first time.
(3) Four main-chain azo polyamides containing ether and sulfone group were synthesized from bis[4-(4-aminophenoxy)phenyl sulfone] and four azobenzene -dicarbonylic chlorides by low-temperature-solution condensation polymerization. The optimum conditions of condensation polymerization were obtained. Inherent Viscosity of four main-chain azo polyamides containing ether and sulfone group is from 0.82-1.12(dl.g~(-1)).
(4) The structures of four main-chain azo polyamides containing ether and sulfone group were confirmed by IR, ~1HNMR and elemental analysis. Incorporation
引文
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