含三氟甲基和不对称结构聚芳酰胺的合成与性能
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摘要
以自制含三氟甲基取代不对称芳香二胺单体——1,4-双(4-氨基-2-三氟甲基苯氧基)-2,3,5-三甲基苯,分别与对苯二甲酸(PTA)、间苯二甲酸(IPA)、4,4-二苯醚二甲酸(OBA)3种商品化二酸单体,经Yamazaki膦酰化法缩聚制得到了一系列新型可溶性聚芳酰胺。该类聚合物的特性黏度在0.68~1.15dL/g之间,具有优异的溶解性能和光学性能。所制聚合物室温下不仅可以溶解在N-甲基-2-吡咯烷酮、N,N-二甲基乙酰胺、N,N-二甲基甲酰胺等沸点较高的有机溶剂中,还能溶解在低沸点的四氢呋喃溶剂中;由该类聚合物所制得的薄膜无色透明,截断波长在331~345nm之间,500nm处的透过率均超过82%。此外该聚芳酰胺还表现出了良好的热学性能和力学性能:玻璃化转变温度在257℃以上,在空气和氮气中10%热失重时的温度分别在413℃和441℃以上;其薄膜的拉伸强度为77.5~88.4 MPa,断裂伸长率在13%~31%,杨氏弹性模量在1.8~2.0GPa。
A series of aromatic polyamides were prepared from 1,4-bis(4-amino-2-trifluorom-ethylphenoxy)-2,3,5-trimethylbenzene and three commercialized aromatic acids(terephthalic acid(PTA),isophthalic acid(IPA),4,4′-oxybisbenzoic acid(OBA))by means of Yamazaki phosporylation technique.The inherent viscosities of the resulted polyamides are in range of 0.68~1.15dL/g.They could be easily dissolved not only in some strong polar organic solvents,such as N-methyl-2-pyrrolidone(NMP), N,N-dimethylacetamide(DMAc),and N,N-dimethylformamide(DMF),but also have good solubility in low-boiling-point solvent THF.The polyamide films show high optical transparency and colorless,with a UV-Vis absorption edge between 331 nm and 345 nm,the transmittance at 500 nm is higher than 82%.The polyamides also possess good thermal and mechanical properties.The glass-transition temperatures are high than 257℃,and the temperature at 10% mass loss is beyond 413 ℃in both air and nitrogen atmospheres,and the polyamide films have tensile strength of 77.5~88.4 MPa,elongation at break of 13%~31%,and elastic modulus of 1.8~2.0GPa.
A series of aromatic polyamides were prepared from 1,4-bis(4-amino-2-trifluorom-ethylphenoxy)-2,3,5-trimethylbenzene and three commercialized aromatic acids(terephthalic acid(PTA),isophthalic acid(IPA),4,4′-oxybisbenzoic acid(OBA))by means of Yamazaki phosporylation technique.The inherent viscosities of the resulted polyamides are in range of 0.68~1.15dL/g.They could be easily dissolved not only in some strong polar organic solvents,such as N-methyl-2-pyrrolidone(NMP), N,N-dimethylacetamide(DMAc),and N,N-dimethylformamide(DMF),but also have good solubility in low-boiling-point solvent THF.The polyamide films show high optical transparency and colorless,with a UV-Vis absorption edge between 331 nm and 345 nm,the transmittance at 500 nm is higher than 82%.The polyamides also possess good thermal and mechanical properties.The glass-transition temperatures are high than 257℃,and the temperature at 10% mass loss is beyond 413 ℃in both air and nitrogen atmospheres,and the polyamide films have tensile strength of 77.5~88.4 MPa,elongation at break of 13%~31%,and elastic modulus of 1.8~2.0GPa.
引文
[1]García J M,García F C,Serna F,et al.High-performance aromatic polyamides[J].Prog.Polym.Sci.,2010,35:623-686.
[2]李鹏辉,汪称意,江建明,等.新型可溶性透明聚芳酰胺的合成与表征[J].中国塑料,2009,23(9):30-35.Li P H,Wang C Y,Jiang J M,et al.Synthesis and characterization of novel soluble and optically transparent aromatic polyamides[J].China Plastics,2009,23(9):30-35.
[3]陈云云,陈文涛,汪称意,等.一类含烷基取代刚性二胺单体及其聚酰亚胺的合成与表征[J].高分子材料科学与工程,2014,30(10):28-32.Chen Y Y,Chen W T,Wang C Y,et al.Synthesis and characterization of rigid aromatic diamine and its polyimides with alkyl groups[J].Polymer Materials Science&Engineering,2014,30(10):28-32.
[4]王沛,刘建东,蹇锡高,等.含间甲基取代杂萘联苯结构共聚芳酰胺的合成与性能[J].高分子材料科学与工程,2006,22(2):83-89.Wang P,Liu J D,Jian X G,et al.Synthesis and properties of copolyamides from MM-HPPZ/NDA/OBBA[J].Polymer Materials Science&Engineering,2006,22(2):83-89.
[5]Zhu X L,Jian X G.Soluble aromatic poly(ether amide)s containing aryl-,alkyl-,and chloro-substituted phthalazinone segments[J].J.Polym Sci.Part A:Polym.Chem.,2004,42(8):2026-2030.
[6]Yaw T C,Jeng Y T.Low dielectric constant and high organosolubility of novel polyimide derived from unsymmetric 1,4-bis(4-aminophenoxy)-2,6-di-tert-butyl-benzene[J].Macromolecules,2008,41:9556-9564.
[7]Mahua G D,Susanta B.Fluorinated high-performance polymers:poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups[J].Prog.Polym.Sci.,2010,35:1022-1077.
[8]Ge Z Y,Yang S Y,Tao Z Q,et al.Synthesis and characterization of novel soluble fluorinated aromatic polyamides derived from fluorinated isophthaloyl dichlorides and aromatic diamines[J].Polymer,2004,45:3627-3635.
[9]Sheng S R,Pei X L,Huang Z Z,et al.Novel soluble fluorinated aromatic polyamides derived from 2-(4-trifluoromethylphenoxy)terephthaloyl chloride with various aromatic diamines[J].Eur.Polym.J.,2009,45:230-236.
[10]李羽中,姜建文,刘晓玲,等.一种氟化含吡啶和氧化三苯膦结构聚酰胺的合成与表征[J].高分子材料科学与工程,2014,30(4):35-39.Li Y Z,Jiang J W,Liu X L,et al.Synthesis and characterization of fluorinated polyamide bearing pyridine and triphenylphosphine oxide moieties[J].Polymer Materials Science&Engineering,2014,30(4):35-39.
[11]Wang C Y,Zhao X Y,Li G.Synthesis and characterization of new fluorinated polyimides derived from an unsymmetical and noncoplanar diamine[J].Chin.J.Chem.,2012,30:2466-2472.
[2]李鹏辉,汪称意,江建明,等.新型可溶性透明聚芳酰胺的合成与表征[J].中国塑料,2009,23(9):30-35.Li P H,Wang C Y,Jiang J M,et al.Synthesis and characterization of novel soluble and optically transparent aromatic polyamides[J].China Plastics,2009,23(9):30-35.
[3]陈云云,陈文涛,汪称意,等.一类含烷基取代刚性二胺单体及其聚酰亚胺的合成与表征[J].高分子材料科学与工程,2014,30(10):28-32.Chen Y Y,Chen W T,Wang C Y,et al.Synthesis and characterization of rigid aromatic diamine and its polyimides with alkyl groups[J].Polymer Materials Science&Engineering,2014,30(10):28-32.
[4]王沛,刘建东,蹇锡高,等.含间甲基取代杂萘联苯结构共聚芳酰胺的合成与性能[J].高分子材料科学与工程,2006,22(2):83-89.Wang P,Liu J D,Jian X G,et al.Synthesis and properties of copolyamides from MM-HPPZ/NDA/OBBA[J].Polymer Materials Science&Engineering,2006,22(2):83-89.
[5]Zhu X L,Jian X G.Soluble aromatic poly(ether amide)s containing aryl-,alkyl-,and chloro-substituted phthalazinone segments[J].J.Polym Sci.Part A:Polym.Chem.,2004,42(8):2026-2030.
[6]Yaw T C,Jeng Y T.Low dielectric constant and high organosolubility of novel polyimide derived from unsymmetric 1,4-bis(4-aminophenoxy)-2,6-di-tert-butyl-benzene[J].Macromolecules,2008,41:9556-9564.
[7]Mahua G D,Susanta B.Fluorinated high-performance polymers:poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups[J].Prog.Polym.Sci.,2010,35:1022-1077.
[8]Ge Z Y,Yang S Y,Tao Z Q,et al.Synthesis and characterization of novel soluble fluorinated aromatic polyamides derived from fluorinated isophthaloyl dichlorides and aromatic diamines[J].Polymer,2004,45:3627-3635.
[9]Sheng S R,Pei X L,Huang Z Z,et al.Novel soluble fluorinated aromatic polyamides derived from 2-(4-trifluoromethylphenoxy)terephthaloyl chloride with various aromatic diamines[J].Eur.Polym.J.,2009,45:230-236.
[10]李羽中,姜建文,刘晓玲,等.一种氟化含吡啶和氧化三苯膦结构聚酰胺的合成与表征[J].高分子材料科学与工程,2014,30(4):35-39.Li Y Z,Jiang J W,Liu X L,et al.Synthesis and characterization of fluorinated polyamide bearing pyridine and triphenylphosphine oxide moieties[J].Polymer Materials Science&Engineering,2014,30(4):35-39.
[11]Wang C Y,Zhao X Y,Li G.Synthesis and characterization of new fluorinated polyimides derived from an unsymmetical and noncoplanar diamine[J].Chin.J.Chem.,2012,30:2466-2472.