N-苯基马来酰亚胺的合成及应用研究
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摘要
N-苯基马来酰亚胺俗称“单马”,英文名称为;N-phenyl maleimide、1-Phenyl-1H-pyrrole-2,5-dione、N-phenylmaleic imide、Maleimidobenzene,英文缩写NPMI,淡黄色片状晶体,熔点为88～92℃,是近年发展起来的一种耐热有机单体,由于它具有五元环状平面结构,嵌入高分子链中可增加链的内旋阻力,从而提高材料的耐热性。目前,NPMI主要用途是作为ABS耐热改性剂,可以有效地改善ABS树脂的耐热性、加工性能、相容性和耐冲击性能。另外,NPMI还可用作PS、PMMA、PP、PVC等热塑性塑料的交联剂和耐热改性剂。未见有NPMI改性热固性树脂和玻璃钢的相关文献和研究报导。
作者首先综述了N-苯基马来酰亚胺的应用及研究进展(主要包括耐热改性剂、光学原材料、医药中间体、防污剂等)、与乙烯基单体的共聚研究进展(主要包括交替共聚、三元共聚、其他共聚等)、阻燃N-苯基马来酰亚胺的研究进展(主要包括应用、合成等)、各种合成方法的优缺点和国内外合成研究进展(主要包括一步法、脱酸法、酯化法、共沸法、醋酐法等)。
本论文以顺丁烯二酸酐和苯胺为原料,以二甲苯和DMF的混合溶液作溶剂,苯醌为阻聚剂,选择醋酐法(两步法)合成NPMI(N-苯基马来酰亚胺)。产品通过红外光谱、气相色谱、核磁共振等进行了表征。在合成N-苯基马来酰亚胺的研究基础上,对N-苯基马来酰亚胺的应用进行了研究;与苯乙烯的共聚研究、改性不饱和聚酯树脂研究、改性不饱和聚酯树脂型玻璃钢研究、在粉末消光树脂中的应用研究。对材料的耐热性能、力学性能、微观结构等进行了表征和研究。研究了N-苯基马来酰亚胺的Gaussian理论计算。主要研究结果如下;
1.采用两步法合成了NPMI(N-苯基马来酰亚胺),以顺丁烯二酸酐和苯胺为原料,二甲苯和DMF的混合溶液作溶剂,以复配型催化剂(酸催化型)催化,产品收率可以达到90%,纯度达到98.15%。合成N-苯基马来酰亚胺的最佳工艺条件为;原料摩尔配比(苯胺;顺酐)为1;1.2;溶剂(二甲苯;DMF)为20;1;初期反应温度为40～50℃,环化反应温度为135℃;环化时间为2h。反应体系中过量的顺丁烯二酸酐可以通过萃取的方法回收利用。萃取温度80℃左右,萃取水量约为过量顺酐的5倍,顺丁烯二酸酐的回收率可以达到80%。
2.N-苯基马来酰亚胺在苯乙烯中溶解度呈线性关系。5～35℃温度范围内,S=0.01t;40～60℃温度范围内,S=0.42+0.022(t-40)。N-苯基马来酰亚胺-苯乙烯沉淀聚合的最佳工艺条件为;乙醇作溶剂,引发剂浓度[BPO]=3×10~(-3)mol/L,单体浓度(单体摩尔比1;1)[NPMI+St]=0.7mol/L,聚合反应温度80℃,聚合反应时间5h。转化率可以达到98%。NPMI-St共聚是按交替方式进行的。
3.首次将N-苯基马来酰亚胺应用于不饱和聚酯树脂体系。N-苯基马来酰亚胺的引入可以有效提高UP树脂浇注体的耐热性。NPMI用量在2～8%范围内,可以将UP树脂浇注体的热变形温度平均提高4～5℃。UP玻璃钢的热变形温度平均提高7～8℃。
4.N-苯基马来酰亚胺的引入对UP树脂浇注体的力学性能有较大的影响。当N-苯基马来酰亚胺用量为2%时,UP树脂浇注体的拉伸强度最大提高了5.5%,达到67.3MPa;N-苯基马来酰亚胺改性UP玻璃钢的拉伸强度值最大可以提高6%,达到261MPa。当N一苯基马来酰亚胺用量为6%时,UP浇注体的冲击强度最大提高了23%,达到8.6KJ/m~2。NPMI改性UP玻璃钢的冲击强度值最大可以提高5%,达到310 KJ/m~2。
5.首次将N-苯基马来酰亚胺应用于热固性粉末涂料。引入N-苯基马来酰亚胺的粉术消光树脂的Tg控制在70℃左右,甲基丙烯酸缩水甘油酯含量为20%时,涂膜的表观、附着力、光泽度均达到了无光粉末涂料的质量要求,所制得的粉末涂料的涂膜性能最佳,涂膜附着力为1级,光泽度(60°)只有4%。N-苯基马来酰亚胺的引入提高了涂膜的耐热老化性能。
6.利用Gaussian 03软件的B3LYP/6-31G基组对N-苯基马来酰亚胺和马来酸酐单体的几何构型进行了模拟和计算。对比研究了N-苯基马来酰亚胺和马来酸酐单体的原子电荷分布,N-苯基马来酰亚胺的苯环和N原子对C=C双键的影响并不明显,反而对五元环上其他C原子、H原子和O原子有一定的影响。通过对N-苯基马来酰亚胺的Gaussian计算,验证了N-苯基马来酰亚胺的红外光谱和~1H NMR的Gaussian计算值与实际测试值基本相符。
N-phenyl maleimide,1-Phenyl-1H-pyrrole-2,5-dione,N-phenylmaleic imide、Maleimidobenzene is abbreviated NPMI or N-PMI,pale-yellow aciform crystals.The melting point is 88～92℃.NPMI is a kind of heat resisting organic monomer,and can increase material thermostability by raising intemal rotation resistance of macromolecular,using its special molecular struture.NPMI is mainly used as heat resisting modifier today,and can effectively improve heat resistance,processibility, compatibility of polymers and impact properties.NPMI is also used as crosslinking agent and heat resisting agent of PS,PMMA,PP and PVC.The report on using to modify,thermosetting resins and glass fibre reinforced plastics(GFRP)have not been detected.
In this paper the writer summarizes application and studies of N-phenyl maleimide,mainly consisting of heat resisting modifier,optical materials,medicine intermediate,and antifouling compound etc.,and study evolutions on copolymerization with vinyl monomers,mainly consisting of alternating copolymerization,terpolymerization and other copolymerization etc.,and study evolutions on flame-resisting N-phenyl maleimide,including application and synthesis etc.,and the advantages and disadvantages of different synthesis,involving one step way,deacidification method,esterification method,azeotropy method and acetic anhydride method etc..
The preparation of N-phenyl maleimide(NPMI)is studied in this paper.Using aniline and maleic anhydride as raw materials,and mixture of xylene and DMF as solvent,and benzoquinone as polymerization inhibitor,N-phenyl maleimide is synthesized through the acetic anhydride method(one step way).The product is characterized by FTIR(Fourier transform infrared spectroscopy),GC(Gas Chromatography)and NMR(Nuclear Magnetic Resonance).The application of N-phenyl maleimide is studied in this paper also,including copolymerization with styrene,modifycation with unsaturated polyester resins and FRP.The modified materials are characterized by heat-resistant properties,mechanical behaviours and microstructures.The results are specialized as follows.
1.The appropriate reaction conditions of synthesis of NPMI are that,the mole ratio of raw material(maleic anhydride;aniline)is 1∶1.2,and the ratio of mix-solvent (xylene;DMF)is 20∶1,and the temperature of the first-step reaction is 40～50℃,and the optimum conditions of the second-step reaction are 135℃and 2h.The composite catalyzer(acid catalyze)can effectively catalyze cyclize reaction on the sysnthesis of N-phenyl maleimide.The yield of NPMI arrives at 90%,and the purity is 98.15%. The superfluous maleic anhydride can be reclaimed by extraction.The extraction temperature is 80℃,and the dosage of water for extraction is 5 times to the quantity of maleic anhydride.The reclaime rate of maleic anhydride arrives at 80%.
2.The solubility curve of NPMI in styrene is linear relationship;5～350℃,S= 0.01t and 40～60℃,S=0.42+0.022(t-40).The appropriate reaction conditions of precipitation polymerization Of NPMI and styrene are that,[BPO]=3×10~(-3)mol/L, [NPMI+St]= 0.7mol/L,and the optimum conditions of copolymerization are 80℃and 5h.The fractional conversion of copolymer arrives at 98%.The reaction is in progress of alternating copolymerization.
3.The heat resistance properties of the modified UP resin casts are improved significantly.The heat-resistant temperature increases 4～5℃when the dosage of NPMI is 2～8%.The heat-resistant temperature of modified FRP increases 7～8℃average.
4.The maximum tensile strength of modified UP resin cast increases 5.5%, reaches 67.3MPa and the maximum tensile strength of modified FRP increases 6%, reaches 261MPa while the usage of NPMI is 2%.The maximum impact strength of modified UP resin cast increases 23%,and the maximum impact strength of modified FRP increases 5%,reaches 310KJ/m~2 reaches 8.6KJ/m~2 when the usage of NPMI is 6%.
5.The optimum conditions for synthesizing the polyester cured matting powder coating by introducing N-phenyl maleimide are determined,comprising controlling glasstransition temperature of the resin at 70℃and GMA content at 20%.The adhesion and lustrousness of the matting powder coating are 1 level and 4% respectively.
6.The geometric configurations of NPMI and MAH are simulated and computed. By contrasting the charge distribution of NPMI and MAH monomers,the influences of benzene ring group and N atom on C=C act insidiously,but on H atom,O atom,C atom of C-C act some distinctness.It is proved that the calculated values of IR and ~1H NMR of N-phenyl maleimide by Gaussian program are in accord with experiment values approximately.
作者首先综述了N-苯基马来酰亚胺的应用及研究进展(主要包括耐热改性剂、光学原材料、医药中间体、防污剂等)、与乙烯基单体的共聚研究进展(主要包括交替共聚、三元共聚、其他共聚等)、阻燃N-苯基马来酰亚胺的研究进展(主要包括应用、合成等)、各种合成方法的优缺点和国内外合成研究进展(主要包括一步法、脱酸法、酯化法、共沸法、醋酐法等)。
本论文以顺丁烯二酸酐和苯胺为原料,以二甲苯和DMF的混合溶液作溶剂,苯醌为阻聚剂,选择醋酐法(两步法)合成NPMI(N-苯基马来酰亚胺)。产品通过红外光谱、气相色谱、核磁共振等进行了表征。在合成N-苯基马来酰亚胺的研究基础上,对N-苯基马来酰亚胺的应用进行了研究;与苯乙烯的共聚研究、改性不饱和聚酯树脂研究、改性不饱和聚酯树脂型玻璃钢研究、在粉末消光树脂中的应用研究。对材料的耐热性能、力学性能、微观结构等进行了表征和研究。研究了N-苯基马来酰亚胺的Gaussian理论计算。主要研究结果如下;
1.采用两步法合成了NPMI(N-苯基马来酰亚胺),以顺丁烯二酸酐和苯胺为原料,二甲苯和DMF的混合溶液作溶剂,以复配型催化剂(酸催化型)催化,产品收率可以达到90%,纯度达到98.15%。合成N-苯基马来酰亚胺的最佳工艺条件为;原料摩尔配比(苯胺;顺酐)为1;1.2;溶剂(二甲苯;DMF)为20;1;初期反应温度为40～50℃,环化反应温度为135℃;环化时间为2h。反应体系中过量的顺丁烯二酸酐可以通过萃取的方法回收利用。萃取温度80℃左右,萃取水量约为过量顺酐的5倍,顺丁烯二酸酐的回收率可以达到80%。
2.N-苯基马来酰亚胺在苯乙烯中溶解度呈线性关系。5～35℃温度范围内,S=0.01t;40～60℃温度范围内,S=0.42+0.022(t-40)。N-苯基马来酰亚胺-苯乙烯沉淀聚合的最佳工艺条件为;乙醇作溶剂,引发剂浓度[BPO]=3×10~(-3)mol/L,单体浓度(单体摩尔比1;1)[NPMI+St]=0.7mol/L,聚合反应温度80℃,聚合反应时间5h。转化率可以达到98%。NPMI-St共聚是按交替方式进行的。
3.首次将N-苯基马来酰亚胺应用于不饱和聚酯树脂体系。N-苯基马来酰亚胺的引入可以有效提高UP树脂浇注体的耐热性。NPMI用量在2～8%范围内,可以将UP树脂浇注体的热变形温度平均提高4～5℃。UP玻璃钢的热变形温度平均提高7～8℃。
4.N-苯基马来酰亚胺的引入对UP树脂浇注体的力学性能有较大的影响。当N-苯基马来酰亚胺用量为2%时,UP树脂浇注体的拉伸强度最大提高了5.5%,达到67.3MPa;N-苯基马来酰亚胺改性UP玻璃钢的拉伸强度值最大可以提高6%,达到261MPa。当N一苯基马来酰亚胺用量为6%时,UP浇注体的冲击强度最大提高了23%,达到8.6KJ/m~2。NPMI改性UP玻璃钢的冲击强度值最大可以提高5%,达到310 KJ/m~2。
5.首次将N-苯基马来酰亚胺应用于热固性粉末涂料。引入N-苯基马来酰亚胺的粉术消光树脂的Tg控制在70℃左右,甲基丙烯酸缩水甘油酯含量为20%时,涂膜的表观、附着力、光泽度均达到了无光粉末涂料的质量要求,所制得的粉末涂料的涂膜性能最佳,涂膜附着力为1级,光泽度(60°)只有4%。N-苯基马来酰亚胺的引入提高了涂膜的耐热老化性能。
6.利用Gaussian 03软件的B3LYP/6-31G基组对N-苯基马来酰亚胺和马来酸酐单体的几何构型进行了模拟和计算。对比研究了N-苯基马来酰亚胺和马来酸酐单体的原子电荷分布,N-苯基马来酰亚胺的苯环和N原子对C=C双键的影响并不明显,反而对五元环上其他C原子、H原子和O原子有一定的影响。通过对N-苯基马来酰亚胺的Gaussian计算,验证了N-苯基马来酰亚胺的红外光谱和~1H NMR的Gaussian计算值与实际测试值基本相符。
N-phenyl maleimide,1-Phenyl-1H-pyrrole-2,5-dione,N-phenylmaleic imide、Maleimidobenzene is abbreviated NPMI or N-PMI,pale-yellow aciform crystals.The melting point is 88～92℃.NPMI is a kind of heat resisting organic monomer,and can increase material thermostability by raising intemal rotation resistance of macromolecular,using its special molecular struture.NPMI is mainly used as heat resisting modifier today,and can effectively improve heat resistance,processibility, compatibility of polymers and impact properties.NPMI is also used as crosslinking agent and heat resisting agent of PS,PMMA,PP and PVC.The report on using to modify,thermosetting resins and glass fibre reinforced plastics(GFRP)have not been detected.
In this paper the writer summarizes application and studies of N-phenyl maleimide,mainly consisting of heat resisting modifier,optical materials,medicine intermediate,and antifouling compound etc.,and study evolutions on copolymerization with vinyl monomers,mainly consisting of alternating copolymerization,terpolymerization and other copolymerization etc.,and study evolutions on flame-resisting N-phenyl maleimide,including application and synthesis etc.,and the advantages and disadvantages of different synthesis,involving one step way,deacidification method,esterification method,azeotropy method and acetic anhydride method etc..
The preparation of N-phenyl maleimide(NPMI)is studied in this paper.Using aniline and maleic anhydride as raw materials,and mixture of xylene and DMF as solvent,and benzoquinone as polymerization inhibitor,N-phenyl maleimide is synthesized through the acetic anhydride method(one step way).The product is characterized by FTIR(Fourier transform infrared spectroscopy),GC(Gas Chromatography)and NMR(Nuclear Magnetic Resonance).The application of N-phenyl maleimide is studied in this paper also,including copolymerization with styrene,modifycation with unsaturated polyester resins and FRP.The modified materials are characterized by heat-resistant properties,mechanical behaviours and microstructures.The results are specialized as follows.
1.The appropriate reaction conditions of synthesis of NPMI are that,the mole ratio of raw material(maleic anhydride;aniline)is 1∶1.2,and the ratio of mix-solvent (xylene;DMF)is 20∶1,and the temperature of the first-step reaction is 40～50℃,and the optimum conditions of the second-step reaction are 135℃and 2h.The composite catalyzer(acid catalyze)can effectively catalyze cyclize reaction on the sysnthesis of N-phenyl maleimide.The yield of NPMI arrives at 90%,and the purity is 98.15%. The superfluous maleic anhydride can be reclaimed by extraction.The extraction temperature is 80℃,and the dosage of water for extraction is 5 times to the quantity of maleic anhydride.The reclaime rate of maleic anhydride arrives at 80%.
2.The solubility curve of NPMI in styrene is linear relationship;5～350℃,S= 0.01t and 40～60℃,S=0.42+0.022(t-40).The appropriate reaction conditions of precipitation polymerization Of NPMI and styrene are that,[BPO]=3×10~(-3)mol/L, [NPMI+St]= 0.7mol/L,and the optimum conditions of copolymerization are 80℃and 5h.The fractional conversion of copolymer arrives at 98%.The reaction is in progress of alternating copolymerization.
3.The heat resistance properties of the modified UP resin casts are improved significantly.The heat-resistant temperature increases 4～5℃when the dosage of NPMI is 2～8%.The heat-resistant temperature of modified FRP increases 7～8℃average.
4.The maximum tensile strength of modified UP resin cast increases 5.5%, reaches 67.3MPa and the maximum tensile strength of modified FRP increases 6%, reaches 261MPa while the usage of NPMI is 2%.The maximum impact strength of modified UP resin cast increases 23%,and the maximum impact strength of modified FRP increases 5%,reaches 310KJ/m~2 reaches 8.6KJ/m~2 when the usage of NPMI is 6%.
5.The optimum conditions for synthesizing the polyester cured matting powder coating by introducing N-phenyl maleimide are determined,comprising controlling glasstransition temperature of the resin at 70℃and GMA content at 20%.The adhesion and lustrousness of the matting powder coating are 1 level and 4% respectively.
6.The geometric configurations of NPMI and MAH are simulated and computed. By contrasting the charge distribution of NPMI and MAH monomers,the influences of benzene ring group and N atom on C=C act insidiously,but on H atom,O atom,C atom of C-C act some distinctness.It is proved that the calculated values of IR and ~1H NMR of N-phenyl maleimide by Gaussian program are in accord with experiment values approximately.
引文
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