Thermally Rearranged Polybenzoxazoles Containing Bulky Adamantyl Groups from Ortho-Substituted Precursor Copolyimides

被引:44
作者
Aguilar-Lugo, Carla [1 ]
Alvarez, Cristina [1 ]
Lee, Young Moo [2 ]
de la Campa, Jose G. [1 ]
Lozano, Angel E. [1 ,3 ,4 ]
机构
[1] CSIC, ICTP, Juan Cierva 3, E-28006 Madrid, Spain
[2] Hanyang Univ, Dept Energy Engn, Seoul 04763, South Korea
[3] Univ Valladolid, CSIC, Fac Ciencias, SMAP,UA UVA,Associated Res Unit, Paseo Belen 7, E-47011 Valladolid, Spain
[4] Univ Valladolid, IU CINQUIMA, Paseo Belen 5, E-47011 Valladolid, Spain
关键词
GAS SEPARATION PROPERTIES; AROMATIC POLYAMIDES; POLY(BENZOXAZOLE-CO-IMIDE) MEMBRANES; TRANSPORT PROPERTIES; POLYMER MEMBRANES; POLYIMIDES; PERMEABILITY; CONVERSION; POLYISOPHTHALAMIDES; PERMSELECTIVITY;
D O I
10.1021/acs.macromol.7b02460
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A new nucleophilic monomer (2,2-bis(3-amino-4-hydroxyphenyl)adamantane, ADHAB) having bulky adamantane groups has been synthesized following an efficient synthetic methodology. The main target of this work was to employ a high thermal stable bulky cycloaliphatic moiety as adamantane to obtain aromatic ortho-hydroxypolyimides (poly(o-hydroxyimide)s) able to thermally rearrange to give polybenzoxazole (TR-PBO) materials that could be tested as gas separation membranes. Thus, an array of ortho-acetylcopolyimides, o-acetyl PIs) were prepared by reaction of ADHAB and 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (APAF) with 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) via chemical imidization. Copolyimides and homopolyimides showed inherent viscosities ranging from 0.49 to 0.70 dL/g and provided good-quality dense membranes. Glass transition temperatures of these o-acetyl copolyimides were higher as the amount of ADHAB increased. The thermal stability of the adamantane moiety during the TR process was evaluated by directly synthesizing PBOs, which were made from the reaction, and ulterior thermal cyclization, of 2,2-bis(4-chlorocarbonylphenyl)-hexafluoropropane with ADHAB/APAF. TR-PBO membranes made through a thermal treatment at 450 degrees C for 30 min showed excellent gas separation properties for the CO2/CH4 gas pair with values close to the 2008 Robeson limit.
引用
收藏
页码:1605 / 1619
页数:15
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