含氟光敏聚酰胺酸酯的合成与性能研究
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摘要
耐高温涂料是一种特殊涂料,它既具有一般涂料的特性,而且还具有耐高温的优点。随着现代高新技术的发展,特别是高速飞行器(如火箭、导弹)的发展,对涂料的耐热性能提出越来越高的要求。UV(ultraviolet,紫外光)固化是一种新型“绿色”辐射固化技术,其应用范围日益扩大。因此研制UV固化耐高温涂料具有一定的现实意义。
在综合分析国内外研究动态的基础上,对所要合成的含氟聚酰胺酸酯进行分子结构及合成工艺路线的设计。以4,4’-六氟亚异丙基-邻苯二甲酸酐(6FDA),均苯四酸二酐(PMDA),4,4,-二氨基二苯醚(ODA),丙烯酸羟乙酯(HEA)为单体,以N-甲基吡咯烷酮(NMP)为溶剂,氮气保护下用直接、混酐、TDI等三种方法分别合成了含氟光敏聚酰胺酸酯(FPAE)。对含氟聚酰胺酸(FPAA)进行粘度测试,实验结果表明:以PMDA,6FDA与ODA为原料合成的含氟聚酰胺酸(FPAA)的最佳工艺条件为:反应温度控制在室温,二酐与二胺摩尔比为1.05~1.15:1,反应时间为3~3.5h。
利用FTIR,UV,TGA等测试手段对合成产物FPAE进行了表征,结果显示:(1)直接法、混酐法、TDI法所合成的含氟光敏聚酰胺酸酯(FPAE)其紫外吸收区分别是:250~340nm,270~370nm,250~340nm;紫外可见光谱的最大吸收波长分别为为267nm、305nm、282nm;(2)在强极性溶剂(NMP、DMF、DMSO)中均具有较好的溶解性;(3)TGA图显示在100~300℃间FPAE均有较大的热失重,这点表明FPAE在100℃时开始酰亚胺化并转化为FPSPI, FPSPI在320~500℃基本保持稳定,500℃开始分解并迅速失重。
选择光引发剂、单体与所合成的FPAE进行复配涂膜,并对固化涂膜进行TGA分析,结果显示:(1)UV固化后的FPAE涂膜在300℃下仍具有耐热性。(2)光热双重固化后的FPAE涂膜在350℃下仍具有耐热性。
High-temperature resistant coating is a kind of special coating. It not only has the characteristics of ordinary coatings, but also has the merit of high-temperature resisting. Along with the development of high-tech, especially the development of high-speed aircraft (such as rocket and missile), more demand has been put forward for high-temp- -erature resisting capability of coatings.UV curing is a new“green”radiation curing technology and its application range expands increasingly. Therefore, developing UV curing high-temperature resistant coating has practical significance.
Based on synthetic analysis of research developments at home and abroad, the molecular structure and synthesis technology route of fluoride polyamide acid ester had been designed. In this paper, synthesis of fluorine poly (amic ester) (FPAE) by using 4,4’-(hexafluoroisopropylidene) diphthalic anhydride (6FDA), pyromellitic dianhydride (PMDA), 4,4’-oxydianiline (ODA) and hydroxyl ethyl acrylate (HEA) as monomers, and N-methyl-pyrrollidone (NMP) as solvent, was conducted in nitrogen atmosphere. Meanwhile, the synthesis of FPAE by three methods(direct method, mixed anhydride method, TDI method) was carried out and the products’viscosity had been tested. The experiment results shows that the optimum reaction conditions of fluorine polyamide acid (FPAA) synthesis in room temperature are as following: n(6FDA+PMDA):nODA=1.05~1.15, reaction time 3~3.5h.
FPAE was characterized by Fourier-trasform infrared spectroscopy (FTIR), ultraviolet spectroscopy (UV), thermal gravimetric analysis (TGA).The results are as following:(1)The wavelength absorption range of UV spectrum of the three products ,which was respectively prepared by direct method, mixed anhydride method and TDI method, are 250~340nm,270~370nm,250~340nm;the maximal wavelength absorption of UV spectrum are respectively 267nm,305nm,282nm; (2) They have good solubility in strong polar solvent(NMP,DMF,DMSO); (3)TGA curves show that FPAE lose weight obviously in the temperature range of 100~300℃, which reflects that FPAE starts imidization and transforms to FPSPI at 100℃. FPSPI does not change significantly in the temperature range of 320-500℃and starts decomposition at 500℃leading to losing weight rapidly.
Choosing photoinitiators, monomer and FPAE to make compound coating film, then TGA was use to analyze the solidified coating film. The results are as following: (1) FPAE coating film prepared by UV curing still has heat-resistant property at 300℃;(2) FPAE coating film prepared by UV-heat dual curing still has heat-resistant property at 350℃.
在综合分析国内外研究动态的基础上,对所要合成的含氟聚酰胺酸酯进行分子结构及合成工艺路线的设计。以4,4’-六氟亚异丙基-邻苯二甲酸酐(6FDA),均苯四酸二酐(PMDA),4,4,-二氨基二苯醚(ODA),丙烯酸羟乙酯(HEA)为单体,以N-甲基吡咯烷酮(NMP)为溶剂,氮气保护下用直接、混酐、TDI等三种方法分别合成了含氟光敏聚酰胺酸酯(FPAE)。对含氟聚酰胺酸(FPAA)进行粘度测试,实验结果表明:以PMDA,6FDA与ODA为原料合成的含氟聚酰胺酸(FPAA)的最佳工艺条件为:反应温度控制在室温,二酐与二胺摩尔比为1.05~1.15:1,反应时间为3~3.5h。
利用FTIR,UV,TGA等测试手段对合成产物FPAE进行了表征,结果显示:(1)直接法、混酐法、TDI法所合成的含氟光敏聚酰胺酸酯(FPAE)其紫外吸收区分别是:250~340nm,270~370nm,250~340nm;紫外可见光谱的最大吸收波长分别为为267nm、305nm、282nm;(2)在强极性溶剂(NMP、DMF、DMSO)中均具有较好的溶解性;(3)TGA图显示在100~300℃间FPAE均有较大的热失重,这点表明FPAE在100℃时开始酰亚胺化并转化为FPSPI, FPSPI在320~500℃基本保持稳定,500℃开始分解并迅速失重。
选择光引发剂、单体与所合成的FPAE进行复配涂膜,并对固化涂膜进行TGA分析,结果显示:(1)UV固化后的FPAE涂膜在300℃下仍具有耐热性。(2)光热双重固化后的FPAE涂膜在350℃下仍具有耐热性。
High-temperature resistant coating is a kind of special coating. It not only has the characteristics of ordinary coatings, but also has the merit of high-temperature resisting. Along with the development of high-tech, especially the development of high-speed aircraft (such as rocket and missile), more demand has been put forward for high-temp- -erature resisting capability of coatings.UV curing is a new“green”radiation curing technology and its application range expands increasingly. Therefore, developing UV curing high-temperature resistant coating has practical significance.
Based on synthetic analysis of research developments at home and abroad, the molecular structure and synthesis technology route of fluoride polyamide acid ester had been designed. In this paper, synthesis of fluorine poly (amic ester) (FPAE) by using 4,4’-(hexafluoroisopropylidene) diphthalic anhydride (6FDA), pyromellitic dianhydride (PMDA), 4,4’-oxydianiline (ODA) and hydroxyl ethyl acrylate (HEA) as monomers, and N-methyl-pyrrollidone (NMP) as solvent, was conducted in nitrogen atmosphere. Meanwhile, the synthesis of FPAE by three methods(direct method, mixed anhydride method, TDI method) was carried out and the products’viscosity had been tested. The experiment results shows that the optimum reaction conditions of fluorine polyamide acid (FPAA) synthesis in room temperature are as following: n(6FDA+PMDA):nODA=1.05~1.15, reaction time 3~3.5h.
FPAE was characterized by Fourier-trasform infrared spectroscopy (FTIR), ultraviolet spectroscopy (UV), thermal gravimetric analysis (TGA).The results are as following:(1)The wavelength absorption range of UV spectrum of the three products ,which was respectively prepared by direct method, mixed anhydride method and TDI method, are 250~340nm,270~370nm,250~340nm;the maximal wavelength absorption of UV spectrum are respectively 267nm,305nm,282nm; (2) They have good solubility in strong polar solvent(NMP,DMF,DMSO); (3)TGA curves show that FPAE lose weight obviously in the temperature range of 100~300℃, which reflects that FPAE starts imidization and transforms to FPSPI at 100℃. FPSPI does not change significantly in the temperature range of 320-500℃and starts decomposition at 500℃leading to losing weight rapidly.
Choosing photoinitiators, monomer and FPAE to make compound coating film, then TGA was use to analyze the solidified coating film. The results are as following: (1) FPAE coating film prepared by UV curing still has heat-resistant property at 300℃;(2) FPAE coating film prepared by UV-heat dual curing still has heat-resistant property at 350℃.
引文
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[3]Zhang Junying,Gaelle Windall,Ian W Boyd. UV Curing of Optical Fibre Coatings Using Excimer Lamps[J]. Applied Surface Science,2002,186(1):568~571
[4]Hongbo Liu,Mingcai Chen,Zhitang Huang. The influence ofsilicon-containing acrylate as active diluent on the properties of UV-cured epoxydiacrylate films[M]. European Polymer Journal,2004
[5]Hongbo Liu,Mingcai Chen,Zhitang Huang Zhitang. Preparationand properties of UV-curable acrylate compositions containing[J]. Ploymer Materials Science and Engineering,2005, 21(2):121~124
[6]赵萍.辐射固化市场:各地区的发展趋势[C].第十届亚洲辐射固化国际会议论文集,上海,2005
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[8]马家举,江棂.光纤外层涂料中齐聚物的改性研究[J].山东科技大学学报,2001,20(2):38~40
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[10]Alford Tl,Zou Yl,Kaustubh S Gadre,etal. Integration and electrical characteri- zation of photo sensitive polyimide[J]. J.Vac.Sci.Technol.B,2001,19(3):774~779.
[11]Jay M Cech,Andrew F Burnett,Lisa Knapp. Pre-Imidized photoimageable polyimide as a dielectric for high density multichip modules[J]. Poly.Eng.Sci,1992,32(21):1646~1652
[12]Jia-shen li,Zuo-bang li,Pu-kun zhu. Modification of negative auto-photosensitive polyimide[J]. J.App.Polum.Sci,2000,77:943~947
[13]Hsu Slc,Lee PI,King JS,et al. Synthesis and characterization of a positive-working, Aqueous-base-developzble photosensitive polymide precursor[J].Journal of Applied Polymer Science,2002,86(2):352~358
[14]肖思煜.紫外光固化涂料的发展状况[J].广州化工,2005,33(5):31~33
[15]Fukushima T,Oyama T,Tomoi M. Ionic-bonded negative photosensitive polyimides having pendantaminoalkyl(meth)acrylamide groups[J]. Reactive and Functional Polymers,2003,56:59
[16]Morita K,Ebara K,Shibasaki Y,et al. New positive-type photosensitive polyimide having sulfo groups [J]. Polymer,2003,40:6235~6238
[17]Chen H,Yin J. Synthesis of autophotosensitive hyperbranched polyimides based on 3,3’,4,4'- benzophenonetetracarboxylic dianhydride and 1,3,5-tris (4-amino phenoxy) benzene via end capping of the terminal anhydride groups by ortho-alkylaniline. Journal of Polymer Science[J]. Polym. Chem.,2003,A41(13):2026~2035
[18]Hsu S C,Fan M H. Synthesis and characterization of novel negative-working aqueous base developable photosensitive polyimide precursors[J]. Polym.,2004,45:1101~1108
[19]孙自淑等.光敏聚酰亚胺的发展现状.化工新型材料,2005,33(10):17~20
[20]E.Beynen,J,Roggen,R.Vanhoof. High Rate Single Substrate Polymer Etching for Multi-Chip- Modules(MCM) and Off-Chip-Interconnect Applications[J]. Micro-electron.Eng.Sci,1992,17: 341~344.
[21]彭秧锡.聚酰亚胺新型材料及其应用[J].化学教育,2004,(4):1~7.
[22]秦传香,秦志忠.聚酰亚胺的合成及其膜的制备[J].合成技术及应用,2005,20(20):8~10
[23]吴桂龙.有机可溶性聚异酰亚胺及聚酰亚胺的合成与性能研究[D].河北工业大学硕士论文,2004
[24]江璐霞等.新型顺酐型聚酰亚胺耐高温涂膜材料的研究[J].中国涂料,1997(6):23~25
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