The diamine, 9,9-bis[4-(4-amino-3-hydroxylphenoxy)phenyl]fluorene (BAHPPF) was synthesized by the modified two-step method. Then, a series of acetate-containing copoly(ether-imide)s were prepared by the copolymerization of BAHPPF, 9,9-bis(4-aminophenyl)fluorene (BAF) and 2,2′-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) followed by chemical imidization. The structures and properties of the BAHPPF and copoly(ether-imide)s were characterized by nuclear magnetic resonance spectrometer (NMR), Fourier transform infrared spectrometer (FTIR), X-ray diffractometer (XRD), differential scanning calorimeter (DSC), thermogravimetric analyzer (TGA), ultraviolet-visible spectrophotometer (UV-VIS), and tensile testing. Single gas permeation performances of these copoly(ether-imide)s were also studied for five representative gases of interest including H2, O2, N2, CO2, and CH4. The experimental results showed that the copoly(ether-imide)s showed excellent optical properties with high light transmittance above 80.2% at 450 nm. The glass transition temperature of these copolymers were higher than 333°C. Their tensile strength and Young’s module also increased, and the elongation decreased with the decrease of BAHPPF. High gas permeabilities of copoly(ether-imide)s were obtained, and the ideal selectivity of CO2/CH4 was improved due to the introduction of acetate group and flexible ether linkage. These copoly(ether-imide)s could be applied to the field of optics and gas separation.
LiFShenJLiuX, et al.Flexible QLED and OPV based on transparent polyimide substrate with rigid alicyclic asymmetric isomer. Org Electron2017; 51: 54–61.
3.
YangYParkJHJungY, et al.Effect of fluorination on haze reduction in transparent polyimide films for flexible substrates. J Appl Polym Sci2017; 134: 44375.
4.
NiHJLiuJGWangZH, et al.A review on colorless and optically transparent polyimide films: chemistry, process and engineering applications. J Ind Engin Chem2015; 28: 16–27.
5.
HeXDuanFLiuJ, et al.Transparent electrode based on silver nanowires and polyimide for film heater and flexible solar cell. Materials2017; 10: 1362.
6.
DamaceanuMDConstantinCPNicolescuA, et al.Highly transparent and hydrophobic fluorinated polyimide films with ortho-kink structure. Eur Polym J2014; 50: 200–213.
7.
ZhangRLiTZhouH, et al.Biobased transparent polyimides with excellent solubility and mechanical properties using myo-inositol derived diamines. React Funct Polym2018; 128: 91–96.
8.
HuangXPeiXWangL, et al.Design and synthesis of organosoluble and transparent polyimides containing bulky substituents and noncoplanar structures. J Appl Polym Sci2016; 133: 43266.
9.
LiuJGHeMHZhouHW, et al.Organosoluble and transparent polyimides derived from alicyclic dianhydride and aromatic diamines. J Polym Sci A Polym Chem2002; 40: 110–119.
10.
ZhaiLYangSFanL. Preparation and characterization of highly transparent and colorless semi-aromatic polyimide films derived from alicyclic dianhydride and aromatic diamines. Polymer2012; 53: 3529–3539.
11.
ChenGZhouYMaK, et al.Synthesis and properties of transparent polyimides derived from 1,4-cyclohexylene bis(trimellitate anhydride). High Perform Polym2017; 4: 1–9.
12.
MiZLiuZYaoJ, et al.Transparent and soluble polyimide films from 1,4:3,6-dianhydro-D-mannitol based dianhydride and diamines containing aromatic and semiaromatic units: preparation, characterization, thermal and mechanical properties. Polym Degrad Stabil2018; 151: 80–89.
13.
YuHCJungJWChoiJY, et al.Structure-property relationship study of partially aliphatic copolyimides for preparation of flexible and transparent polyimide films. J Macromol Sci A Pure Appl Chem2017; 54: 97–104.
14.
YuHCJungJWChoiJY, et al.Kinetic Study of low-temperature imidization of poly(amic acid)s and preparation of colorless, transparent polyimide films. J Polym Sci A: Polym Chem2016; 54: 1593–1602.
15.
WangQWangQJiangW. Patent analysis of the colorless transparent polyimide. Inform Record Mater2018; 10: 3–6.
16.
YiLLiCHuangW, et al.Soluble and transparent polyimides with high Tg from a new diamine containing tert-butyl and fluorene units. J Polym Sci A: Polym Chem2016; 54: 976–984.
17.
ZhuangYSeongJGYuSD, et al.Intrinsically microporous soluble polyimides incorporating Tröger’s base for membrane gas separation. Macromolecules2014; 47: 3254–3262.
18.
YahayaGOQahtaniMSAmmarAY, et al.Aromatic block co-polyimide membranes for sour gas feed separations. Chem Eng J2016; 304: 1020–1030.
19.
Sulub-SulubRLoría-BastarracheaMIVázquez-TorresH, et al.Highly permeable polyimide membranes with a structural pyrene containing tert-butyl groups: synthesis, characterization and gas transport. J Membr Sci2018; 563:134–141.
20.
AlmasriMKricheldorfHRFritschD. New polyimides for gas separation. 1. polyimides derived from substituted terphenylenes and 4,4′-(hexafluoroisopropylidene)diphthalic anhydride. Macromolecules1999; 32: 7853–7858.
21.
WangZWangDZhangF, et al.Tröger’s base-based microporous polyimide membranes for high-performance gas separation. ACS Macro Letters2014; 3: 597–601.
22.
CalleMGarcíaCLozanoAE, et al.Local chain mobility dependence on molecular structure in polyimides with bulky side groups: correlation with gas separation properties. J Membr Sci2013; 434: 121–129.
23.
RobesonLM. Correlation of separation factor versus permeability for polymeric membranes. J Membr Sci1991; 62: 165.
24.
RobesonLM. The upper bound revisited. J Membr Sci2008; 320: 390–400.
25.
YampolksiiYPBanerjeeS. Effects of bulky substituents on transport properties of membrane gas separation materials. Petrol Chem2017; 57: 1195–1206.
26.
Staudt-BickelCKorosWJ. Olefin/paraffin gas separations with 6FDA-based polyimide membranes. J Membr Sci2000; 170: 205–214.
27.
XiaoSHuangRYMFengX. Synthetic 6FDA-ODA copolyimide membranes for gas separation and pervaporation: functional groups and separation properties. Polymer2007; 48: 5355–5368.
28.
KanehashiSSatoSNagaiK. Membrane color and gas permeability of 6FDA-TeMPD polyimide membranes prepared with various membrane preparation protocols. Polym Eng Sci2011; 51: 2360–2369.
29.
TanPCOoiBSAhmadAL, et al.Monomer atomic configuration as key feature in governing the gas transport behaviors of polyimide membrane. J Appl Polym Sci2017; 135: 46073.
30.
KhoshkamMSadeghiMChenarMP, et al.Synthesis, characterization and gas separation properties of novel copolyimide membranes based on flexible etheric–aliphatic moieties. Rsc Adv2016; 6: 35751–35763.
31.
YoshiokaTKojimaKShindoR, et al.Gas-separation properties of amine-crosslinked polyimide membranes modified by amine vapor. J Appl Polym Sci2017; 134: 1–9.
32.
ZhuangYSeongJGYuSD, et al.High-strength, soluble polyimide membranes incorporating Tröger’s Base for gas separation. J Membr Sci2016; 504: 55–65.
33.
MaXAbdulhamidMMiaoX, et al.Facile synthesis of a hydroxyl-functionalized Tröger’s Base diamine: a new building block for high-performance polyimide gas separation membranes. Macromolecules2017; 50: 9569–9576.
34.
JinXZIshiiH. A novel positive-type photosensitive polyimide having excellent transparency based on soluble block copolyimide with hydroxyl group and diazonaphthoquintone. J Appl Polym Sci2010; 96: 1619–1624.
35.
AlaslaiNGhanemBAlghunaimiF, et al.High-performance intrinsically microporous dihydroxyl-functionalized triptycene-based polyimide for natural gas separation. Polymer2016; 91: 128–135.
36.
AlghunaimiFGhanemBAlaslaiN, et al.Triptycene dimethyl-bridgehead dianhydride-based intrinsically microporous hydroxyl-functionalized polyimide for natural gas upgrading. J Membr Sci2016; 520: 240–246.
37.
JungCHLeeYM. Gas permeation properties of hydroxyl-group containing polyimide membranes. Macromol Res2008; 16: 555–560.
38.
XuYFeiFZhaoJ, et al.Preparation and characterization of novel polyimides with hydroxyl groups. J Macromol Sci B Phys2011; 50: 2090–2102.
39.
ShenJZhangYHuangM, et al.Study on preparation and properties of novel reactive phenolic hydroxyl-containing polyimides. J Polym Res2012; 19: 1–9.
40.
MaXSalinasOLitwillerE, et al.Pristine and thermally-rearranged gas separation membranes from novel o-hydroxyl-functionalized spirobifluorene-based polyimides. Polym Chem2014; 5: 6914–6922.
41.
LiuWFXieW. Acetate-functional thermally rearranged polyimides based on 2,2-bis(3-amino-4-hydroxy-phenyl)hexafluoropropane (APAF) and various dianhydrides for gas separations. Ind Eng Chem Res2013; 53: 871–879.
42.
ParkSHKimKJSoWW, et al.Gas separation properties of 6FDA-based polyimide membranes with a polar group. Macromol Res2003; 11: 157–162.
43.
SwaidanRGhanemBLitwillerE, et al.Effects of hydroxyl-functionalization and sub-Tg thermal annealing on high pressure pure- and mixed-gas CO2/CH4 separation by polyimide membranes based on 6FDA and triptycene-containing dianhydrides. J Membr Sci2015; 475: 571–581.
44.
ChangJHParkKMLeeSM, et al.Two-step thermal conversion from poly(amic acid) to polybenzoxazole via polyimide: their thermal and mechanical properties. J Polym Sci B Polym Phys2015; 38: 2537–2545.
45.
LeeBMKimDJNamSY. Effect of bulky and hydroxyl groups on gas separation performance of polyimide membranes. J Nanosci Nanotech2015; 15: 2351–2355.
46.
DasguptaBBanerjeeS. A study of gas transport properties of semifluorinated poly(ether imide) membranes containing cardo diphenylfluorene moieties. J Membr Sci2010; 362: 58–67.
47.
ImaiYShibasakiYTakeuchiH, et al.Synthesis and properties of soluble aromatic poly(ether benzoxazole)s from 9,9-bis[4-(4-amino-3-hydroxyphenoxy)phenyl]fluorene and aromatic dicarboxylic acid chlorides. High Perform Polym2002; 14: 253–260.
48.
WuYHZhouJLZhangB, et al.Fabrication and gas permeation of CMS/C composite membranes based on polyimide and phenolic resin. RSC Adv2016; 6: 75390–75399.
49.
CalleMLeeYM. Thermally rearranged (TR) poly(ether-benzoxazole) membranes for gas separation. Macromolecules2011; 44: 1156–1165.
50.
SumanKSSusantaB. Gas transport properties of fluorinated poly(ether imide) films containing phthalimidine moiety in the main chain. J Membr Sci2010; 350: 53–61.
