含活性基团亚胺/多官能环氧的制备及其固化反应动力学研究
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摘要
随着航天航空等领域的高速发展,对高性能材料的需求也日益紧迫。环氧树脂以其良好的力学性能、优异的绝缘性能、好的粘合力、较小的收缩率、较好的稳定性等性能而被广泛地应用。但环氧树脂的耐冲击损伤能力差、韧性差、耐热性能也较低等缺点大大限制了其应用。因此提高环氧树脂的耐高温性能势在必行。而聚酰亚胺的综合性能优异,尤其耐高温性能较好。本论文设计并制备含活性基团的耐高温聚酰亚胺,将其用于环氧树脂改性,可以综合两者的优点,得到具有良好机械性能和高粘结强度的耐高温环氧固化物。
本论文首先合成了具有活性基团羟基的芳香族二元胺和聚酰亚胺,活性基团羟基的引入在保证聚酰亚胺耐热性能的同时可以提高聚酰亚胺的溶解性、反应性等。分别将含活性基团羟基的芳香族二元胺和聚酰亚胺引入环氧树脂的固化体系,通过固化反应动力学的研究发现,活性基团羟基的存在对于聚酰亚胺固化环氧树脂N,N,N',N'-四缩水甘油基-4,4’-二氨基二苯甲烷(TGDDM)的反应有利。聚酰亚胺/TGDDM固化动力学的研究为环氧-聚酰亚胺的固化提供了理论依据,同时通过交联反应得到耐热性能和机械性能优异的环氧-聚酰亚胺胶粘剂。本论文通过聚合和热亚胺化两步分别制备含羟基的系列聚酰亚胺薄膜,通过聚合和化学亚胺化两步制备得到含羟基的聚酰亚胺粉末,并对所制备的聚酰亚胺薄膜和聚酰亚胺粉末进行了性能的研究。分别以所制备的含羟基芳香二元胺和含羟基聚酰亚胺粉末为固化剂,研究TGDDM的固化反应动力学。制备得到含羟基聚酰亚胺/环氧树脂胶粘剂,并对胶粘剂进行了性能研究。
本论文的工作包括以下几方面：
1.设计合成了含活性基团羟基的三种芳香族二元胺单体3,3’-二氨基-4,4’-二羟基联苯(DADHBP)、2,2-双(3-氨基-4-羟基苯基)丙烷(BAHPP)和2,2-双(3-氨基-4-羟基苯基)六氟丙烷(BAHPFP),然后通过DSC(测熔点)和傅立叶红外光谱对合成的含羟基的芳香二元胺单体进行表征。
2.3,3’-二氨基-4,4’-二羟基联苯分别与2,2-双[4-(4-氨基苯氧基)苯基]丙烷(BAPOPP)和3,3’,4,4’-四羧酸二苯醚二酐(ODPA)按不同的比例进行聚合和热亚胺化得到八种DADHBP-BAPOPP-ODPA-PI薄膜,2,2-双(3-氨基-4-羟基苯基)丙烷与3,3’,4,4’-四羧酸二苯醚二酐(ODPA)聚合和热亚胺化得到BAHPP-ODPA-PI薄膜,2,2-双(3-氨基-4-羟基苯基)六氟丙烷与3,3’,4,4’-四羧酸二苯醚二酐(ODPA)聚合和热亚胺化得到BAHPFP-ODPA-PI薄膜。并对所获得的系列含羟基聚酰亚胺薄膜进行了傅立叶红外、DSC、TGA、紫外可见光、接触角、表面能、吸水率及机械性能表征。
3.将3,3’-二氨基-4,4’-二羟基联苯(DADHBP)、2,2-双[4-(4-氨基苯氧基)苯基]丙烷(BAPOPP),4,4’-二氨基二苯醚(ODA)与3,3’,4,4’-四羧酸二苯醚二酐(ODPA),3,3’,4,4’-四羧酸二苯甲酮二酐(BTDA)进行缩聚和化学亚胺化反应得到含酚羟基聚酰亚胺(PI),然后对其进行了傅立叶红外光谱的结构表征,通过DSC和TGA对其进行热性能的表征。
4.利用所制备的两种含羟基的芳香族二元胺分别对环氧树脂TGDDM进行固化反应动力学研究。首先对TGDDM/BAHPFP和TGDDM/DADHBP进行DSC的跟踪测试,利用所获得的DSC数据分别用Kissinger方程和Ozawa方程计算得到TGDDM/BAHPFP和TGDDM/DADHBP体系的反应活化能。结果显示该系列体系的固化反应出现两个明显的放热峰,两种计算方法的平均活化能分别为为67.20KJ/mol和121.55KJ/mol (TGDDM/BAHPFP)、110.19KJ/mol和143.89KJ/mol (TGDDM/DADHBP)。通过Crane方程计算得到两体系的两个放热峰的反应级数分别为0.91和0.94(TGDDM/BAHPFP)、0.94和0.95(TGDDM/DADHBP)。利用计算得到的平均反应活化能通过Kissinger和Arrhenius方程计算得到TGDDM/BAHPFP和TGDDM/DADHBP体系固化反应的频率因子A、峰温时的反应速率常数kp。
5.研究了含羟基聚酰亚胺与多官能环氧TGDDM的固化反应动力学。分别对PI/TGDDM和PI/4,4'-二氨基二苯砜DDS/TGDDM胶粘剂体系进行固化反应动力学的研究。两体系分别进行了DSC的跟踪,然后利用DSC的数据通过Kissinger方程和Ozawa方程计算得到两体系的平均反应活化能分别为131.13KJ/mol和108.65KJ/mol。通过Crane方程分别计算得到两体系的反应级数分别为0.93和0.92,说明两反应均为复杂反应。根据计算出的平均反应活化能通过Kissinger方程分别计算两体系固化反应的频率因子A和峰温时的反应速率常数kp。
6.用所制备的聚酰亚胺粉末改性TGDDM环氧树脂,制备含酚羟基聚酰亚胺改性环氧树脂体系的胶粘剂。经固化后得到TGDDM环氧树脂胶粘剂。对TGDDM环氧树脂胶粘剂进行傅立叶红外光谱的结构表征。环氧基团特征吸收峰的消失说明TGDDM环氧树脂胶粘剂的固化反应完全。根据Flory理论由TGDDM环氧树脂胶粘剂的凝胶化时间计算得到TGDDM环氧树脂胶粘剂的表观活化能为64.5kJ/mol。室温下测得TGDDM环氧树脂胶粘剂的吸水率为0.49%。
With the development of aerospace and other fields, the demand for high-performance materials is also increasingly urgent. Epoxy resin with good mechanical properties, excellent insulation properties, high adhesion, low shrinkage, good stability and so on is widely used. However, poor resistance to impact, poor toughness, low heat resistance and other properties of epoxy resin also greatly limit its applications. Therefore, how to improve the heat resistance of epoxy resin is neccesary. In this thesis the polyimide with hydroxyl groups which has excellent properties such as good heat resistance was designed and prepared, then it was used to modify epoxy resin to get the adhesive which will have good mechanical and heat properties.
The diamines and polyimides with reactive hydroxyl groups were synthsized firstly in this thesis. The reactiveties of the prepared polyimides were improved while the heat resistance and mechanical properties of the polyimides were kept. The curing kinetics analysis of N,N,N',N'-tetraglycidyl-4,4'-diamino phenyl methane (TGDDM) with aromatic diamines and polyimide with active hydroxyl groups was studied with DSC methods. The results showed that the reactivities of the curing regents with reactive hydroxyl groups were improved. Meanwhile the data will provide a theoretical basis for the curing of the epoxy resin. The epoxy/polyimide adhesive was got through cross-linking reaction. In this thesis, the diamine monomers of the polyimide containing hydroxyl groups were designed and synthesized. Then the polyimides containing hydroxyl groups were prepared by two-step method and the properties of the polyimides were studied. The curing kinetics of TGDDM with aromatic diamines and polyimide powder containing hydroxyl as curing agent were investigated. Finally, polyimide/epoxy resin adhesive was prepared and its performance was studied.
This thesis mainly contained six parts:
1.3,3'-diamino-4,4'-dihydroxybiphenyl(DADHBP),2,2-Bis(3-amino-4-hydroxy phenyl)propane(BAHPPP),2,2-Bis(3-amino-4-hydroxyphenyl)1,1,1,3,3,3-hexa fluoropropane (BAHPFP) were synthesized through two steps. Then three compounds were characterized by FI-IR and DSC.
2. A series of polyimides were prepared by 3,3'-diamino-4,4'-dihydroxybiphenyl (DADHBP),2,2-bis-[4-(4-aminophenoxy)phenyl]propane(BAPOPP) and,3,3',4,4'-tetracarboxylicdiphenylether dianhydride(ODPA) with different ratios in the presence of dimethylacetamide (DMAC) as solvent.2,2-Bis(3-amino-4-hydroxy phenyl)propane(BAHPPP) and 2,2-Bis(3-amino-4-hydroxyphenyl) 1,1,1,3,3,3-hexafluoropropane (BAHPFP) were reacted with ODPA to get the polyimides. The tests of DSC, TGA, FTIR, UV-visible transmittance, contacting angle, water absorption and mechanical performance were performed on the series of polyimide films.
3. The polyimide powder containing hydroxyl groups was preparared by copolymerizing of DADHBP, BAPOPP, ODPA, and 3,3',4,4'-Benzophenonetetra carboxylicdianhydride (BTDA). Then the polyimide powder was characterized by FTIR, and the thermal properties were studied by DSC and TGA.
4. The exothermic curves of DADHBP and BAHPFP with TGDDM were determined respectively by differential scanning calorimetry (DSC) measurements at different heating rates. The curing kinetics of the two non-isothermal curing processes were studied by Kissinger and Ozawa methods to calculate the average activation energyis were 65.7kJ/mol and 120.2kJ/mol (TGDDM/BAHPFP),109.18kJ/mol and 143.1kJ/mol(TGDDM/DADHBP). The reaction orders were 0.91 and 0.93 (TGDDM/BAHPFP),0.93and 0.94(TGDDM/DADHBP) calculated through Crane equation suggested that the curing processes were complicated. Finally the frequency factor (A) and the reaction rate constant (kp) were calculated by Kissinger and Arrhenius equations.
5. The DSC exothermic curves of the adhesive systems of PI/TGDDM and the PI/DDS/TGDDM (containing curing reagent) were determined. Then the kinetics of the above systems were studied by Kissinger and Ozawa equations to get the average activation energies of 131.13kJ/mol(PI/TGDDM) and 108.65kJ/mol(PI/ DDS/TGDDM), while the reaction order were calculated by Crane equation of 0.93(PI/TGDDM) and 0.92(PI/DDS/TGDDM. Finally the frequency factor (A) and the reaction rate constant (kp) were calculated by the Kissinger equation. The results suggested that the two curing reactions were complicated.
6. The PI/TGDDM adhesive was perepared firstly. Then the PI/TGDDM was cured. The results showed that the water absorption of PI/TGDDM adhesive was 0.49%. The activation energy of PI/TGDDM adhesive was 64.5kJ/mol.
本论文首先合成了具有活性基团羟基的芳香族二元胺和聚酰亚胺,活性基团羟基的引入在保证聚酰亚胺耐热性能的同时可以提高聚酰亚胺的溶解性、反应性等。分别将含活性基团羟基的芳香族二元胺和聚酰亚胺引入环氧树脂的固化体系,通过固化反应动力学的研究发现,活性基团羟基的存在对于聚酰亚胺固化环氧树脂N,N,N',N'-四缩水甘油基-4,4’-二氨基二苯甲烷(TGDDM)的反应有利。聚酰亚胺/TGDDM固化动力学的研究为环氧-聚酰亚胺的固化提供了理论依据,同时通过交联反应得到耐热性能和机械性能优异的环氧-聚酰亚胺胶粘剂。本论文通过聚合和热亚胺化两步分别制备含羟基的系列聚酰亚胺薄膜,通过聚合和化学亚胺化两步制备得到含羟基的聚酰亚胺粉末,并对所制备的聚酰亚胺薄膜和聚酰亚胺粉末进行了性能的研究。分别以所制备的含羟基芳香二元胺和含羟基聚酰亚胺粉末为固化剂,研究TGDDM的固化反应动力学。制备得到含羟基聚酰亚胺/环氧树脂胶粘剂,并对胶粘剂进行了性能研究。
本论文的工作包括以下几方面：
1.设计合成了含活性基团羟基的三种芳香族二元胺单体3,3’-二氨基-4,4’-二羟基联苯(DADHBP)、2,2-双(3-氨基-4-羟基苯基)丙烷(BAHPP)和2,2-双(3-氨基-4-羟基苯基)六氟丙烷(BAHPFP),然后通过DSC(测熔点)和傅立叶红外光谱对合成的含羟基的芳香二元胺单体进行表征。
2.3,3’-二氨基-4,4’-二羟基联苯分别与2,2-双[4-(4-氨基苯氧基)苯基]丙烷(BAPOPP)和3,3’,4,4’-四羧酸二苯醚二酐(ODPA)按不同的比例进行聚合和热亚胺化得到八种DADHBP-BAPOPP-ODPA-PI薄膜,2,2-双(3-氨基-4-羟基苯基)丙烷与3,3’,4,4’-四羧酸二苯醚二酐(ODPA)聚合和热亚胺化得到BAHPP-ODPA-PI薄膜,2,2-双(3-氨基-4-羟基苯基)六氟丙烷与3,3’,4,4’-四羧酸二苯醚二酐(ODPA)聚合和热亚胺化得到BAHPFP-ODPA-PI薄膜。并对所获得的系列含羟基聚酰亚胺薄膜进行了傅立叶红外、DSC、TGA、紫外可见光、接触角、表面能、吸水率及机械性能表征。
3.将3,3’-二氨基-4,4’-二羟基联苯(DADHBP)、2,2-双[4-(4-氨基苯氧基)苯基]丙烷(BAPOPP),4,4’-二氨基二苯醚(ODA)与3,3’,4,4’-四羧酸二苯醚二酐(ODPA),3,3’,4,4’-四羧酸二苯甲酮二酐(BTDA)进行缩聚和化学亚胺化反应得到含酚羟基聚酰亚胺(PI),然后对其进行了傅立叶红外光谱的结构表征,通过DSC和TGA对其进行热性能的表征。
4.利用所制备的两种含羟基的芳香族二元胺分别对环氧树脂TGDDM进行固化反应动力学研究。首先对TGDDM/BAHPFP和TGDDM/DADHBP进行DSC的跟踪测试,利用所获得的DSC数据分别用Kissinger方程和Ozawa方程计算得到TGDDM/BAHPFP和TGDDM/DADHBP体系的反应活化能。结果显示该系列体系的固化反应出现两个明显的放热峰,两种计算方法的平均活化能分别为为67.20KJ/mol和121.55KJ/mol (TGDDM/BAHPFP)、110.19KJ/mol和143.89KJ/mol (TGDDM/DADHBP)。通过Crane方程计算得到两体系的两个放热峰的反应级数分别为0.91和0.94(TGDDM/BAHPFP)、0.94和0.95(TGDDM/DADHBP)。利用计算得到的平均反应活化能通过Kissinger和Arrhenius方程计算得到TGDDM/BAHPFP和TGDDM/DADHBP体系固化反应的频率因子A、峰温时的反应速率常数kp。
5.研究了含羟基聚酰亚胺与多官能环氧TGDDM的固化反应动力学。分别对PI/TGDDM和PI/4,4'-二氨基二苯砜DDS/TGDDM胶粘剂体系进行固化反应动力学的研究。两体系分别进行了DSC的跟踪,然后利用DSC的数据通过Kissinger方程和Ozawa方程计算得到两体系的平均反应活化能分别为131.13KJ/mol和108.65KJ/mol。通过Crane方程分别计算得到两体系的反应级数分别为0.93和0.92,说明两反应均为复杂反应。根据计算出的平均反应活化能通过Kissinger方程分别计算两体系固化反应的频率因子A和峰温时的反应速率常数kp。
6.用所制备的聚酰亚胺粉末改性TGDDM环氧树脂,制备含酚羟基聚酰亚胺改性环氧树脂体系的胶粘剂。经固化后得到TGDDM环氧树脂胶粘剂。对TGDDM环氧树脂胶粘剂进行傅立叶红外光谱的结构表征。环氧基团特征吸收峰的消失说明TGDDM环氧树脂胶粘剂的固化反应完全。根据Flory理论由TGDDM环氧树脂胶粘剂的凝胶化时间计算得到TGDDM环氧树脂胶粘剂的表观活化能为64.5kJ/mol。室温下测得TGDDM环氧树脂胶粘剂的吸水率为0.49%。
With the development of aerospace and other fields, the demand for high-performance materials is also increasingly urgent. Epoxy resin with good mechanical properties, excellent insulation properties, high adhesion, low shrinkage, good stability and so on is widely used. However, poor resistance to impact, poor toughness, low heat resistance and other properties of epoxy resin also greatly limit its applications. Therefore, how to improve the heat resistance of epoxy resin is neccesary. In this thesis the polyimide with hydroxyl groups which has excellent properties such as good heat resistance was designed and prepared, then it was used to modify epoxy resin to get the adhesive which will have good mechanical and heat properties.
The diamines and polyimides with reactive hydroxyl groups were synthsized firstly in this thesis. The reactiveties of the prepared polyimides were improved while the heat resistance and mechanical properties of the polyimides were kept. The curing kinetics analysis of N,N,N',N'-tetraglycidyl-4,4'-diamino phenyl methane (TGDDM) with aromatic diamines and polyimide with active hydroxyl groups was studied with DSC methods. The results showed that the reactivities of the curing regents with reactive hydroxyl groups were improved. Meanwhile the data will provide a theoretical basis for the curing of the epoxy resin. The epoxy/polyimide adhesive was got through cross-linking reaction. In this thesis, the diamine monomers of the polyimide containing hydroxyl groups were designed and synthesized. Then the polyimides containing hydroxyl groups were prepared by two-step method and the properties of the polyimides were studied. The curing kinetics of TGDDM with aromatic diamines and polyimide powder containing hydroxyl as curing agent were investigated. Finally, polyimide/epoxy resin adhesive was prepared and its performance was studied.
This thesis mainly contained six parts:
1.3,3'-diamino-4,4'-dihydroxybiphenyl(DADHBP),2,2-Bis(3-amino-4-hydroxy phenyl)propane(BAHPPP),2,2-Bis(3-amino-4-hydroxyphenyl)1,1,1,3,3,3-hexa fluoropropane (BAHPFP) were synthesized through two steps. Then three compounds were characterized by FI-IR and DSC.
2. A series of polyimides were prepared by 3,3'-diamino-4,4'-dihydroxybiphenyl (DADHBP),2,2-bis-[4-(4-aminophenoxy)phenyl]propane(BAPOPP) and,3,3',4,4'-tetracarboxylicdiphenylether dianhydride(ODPA) with different ratios in the presence of dimethylacetamide (DMAC) as solvent.2,2-Bis(3-amino-4-hydroxy phenyl)propane(BAHPPP) and 2,2-Bis(3-amino-4-hydroxyphenyl) 1,1,1,3,3,3-hexafluoropropane (BAHPFP) were reacted with ODPA to get the polyimides. The tests of DSC, TGA, FTIR, UV-visible transmittance, contacting angle, water absorption and mechanical performance were performed on the series of polyimide films.
3. The polyimide powder containing hydroxyl groups was preparared by copolymerizing of DADHBP, BAPOPP, ODPA, and 3,3',4,4'-Benzophenonetetra carboxylicdianhydride (BTDA). Then the polyimide powder was characterized by FTIR, and the thermal properties were studied by DSC and TGA.
4. The exothermic curves of DADHBP and BAHPFP with TGDDM were determined respectively by differential scanning calorimetry (DSC) measurements at different heating rates. The curing kinetics of the two non-isothermal curing processes were studied by Kissinger and Ozawa methods to calculate the average activation energyis were 65.7kJ/mol and 120.2kJ/mol (TGDDM/BAHPFP),109.18kJ/mol and 143.1kJ/mol(TGDDM/DADHBP). The reaction orders were 0.91 and 0.93 (TGDDM/BAHPFP),0.93and 0.94(TGDDM/DADHBP) calculated through Crane equation suggested that the curing processes were complicated. Finally the frequency factor (A) and the reaction rate constant (kp) were calculated by Kissinger and Arrhenius equations.
5. The DSC exothermic curves of the adhesive systems of PI/TGDDM and the PI/DDS/TGDDM (containing curing reagent) were determined. Then the kinetics of the above systems were studied by Kissinger and Ozawa equations to get the average activation energies of 131.13kJ/mol(PI/TGDDM) and 108.65kJ/mol(PI/ DDS/TGDDM), while the reaction order were calculated by Crane equation of 0.93(PI/TGDDM) and 0.92(PI/DDS/TGDDM. Finally the frequency factor (A) and the reaction rate constant (kp) were calculated by the Kissinger equation. The results suggested that the two curing reactions were complicated.
6. The PI/TGDDM adhesive was perepared firstly. Then the PI/TGDDM was cured. The results showed that the water absorption of PI/TGDDM adhesive was 0.49%. The activation energy of PI/TGDDM adhesive was 64.5kJ/mol.
引文
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