a.Jiangsu Collaborative Innovation Center of Photovoltaic Science and Engineering, Jiangsu Key Laboratory of Environmentally Friendly Polymeric Materials, School of Materials Science and Engineering, Changzhou University, Changzhou 213164, China
b.State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 210009, China
wangcy@cczu.edu.cn (C.Y.W.)
zhaoxiaoyan@cczu.edu.cn (X.Y.Z.)
收稿:2019-10-26,
修回:2020-11-26,
录用:2019-11-28,
网络首发:2020-02-18,
纸质出版:2020-07
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Wang, C. Y.; Jiang, C. R.; Yu, B.; Zhao, X. Y.; Cui, Z. L.; Li, J.; Ren, Q. Highly soluble polyimides containing di-, tert,-butylbenzene and dimethyl groups with good gas separation properties and optical transparency. Chinese J. Polym. Sci. 2020, 38, 759–768
Chen-Yi Wang, Cai-Rong Jiang, Bin Yu, et al. Highly Soluble Polyimides Containing Di-
Wang, C. Y.; Jiang, C. R.; Yu, B.; Zhao, X. Y.; Cui, Z. L.; Li, J.; Ren, Q. Highly soluble polyimides containing di-, tert,-butylbenzene and dimethyl groups with good gas separation properties and optical transparency. Chinese J. Polym. Sci. 2020, 38, 759–768 DOI: 10.1007/s10118-020-2377-y.
Chen-Yi Wang, Cai-Rong Jiang, Bin Yu, et al. Highly Soluble Polyimides Containing Di-
A rigid aromatic diamine monomer containing di-
tert
-butylbenzene and dimethyl groups
3
3′-dimethyl-4
4′-diaminophenyl- 3″
5″-di-
tert
-butyltoluene
was successfully synthesized by a simple coupling reaction using 3
5-di-
tert
-butylbenzaldehyde and
o
-toluidine as starting materials. A series of novel polyimides (
PI 3a
−
3c
) with large pendant groups were prepared with the obtained diamine monomer and three different commercial aromatic dianhydrides (3
3′
4
4′-biphenyltetracarboxylic dianhydride
4
4′-oxydiphthalic anhydride
and 4
4′-(hexafluoroisopropylidene)diphthalic anhydride) by one-step high temperature polycondensation. The prepared polyimides exhibited high solubility and good membrane forming ability: they could be dissolved not only in some high boiling solvents such as DMF
NMP
DMAc
and
m
-Cresol at room temperature
but also in some low boiling solvents such as CHCl
3
CH
2
Cl
2
and THF. Their solubility in most solvents could exceed 10 wt%
and the flexible membranes could be obtained by casting their solutions. The prepared membranes exhibited good gas separation properties. The permeability coefficients of
PI 3c
for CO
2
and O
2
were up to 124.6 and 42.8 barrer
respectively
and the selectivity coefficients for CO
2
/CH
4
and O
2
/N
2
were 14.7 and 3.3
respectively. The membranes had light color and good optical transmission. Their optical transmittance at 450 nm wavelength was in the range of 67%−79%
and the cutoff wavelength was in the range of 310−348 nm. They also had good thermal properties with glass transition temperature (
T
g
) values in the range of 264−302 °C. In addition
these membranes possessed good mechanical properties with tensile strength ranging between 77.8−87.4 MPa
initial modulus ranging between 1.69−1.82 GPa
and elongation at break ranging between 4.8%−6.1%.
Mosanenzadeh, S. G.; Saadatnia, Z.; Shi, F.; Park, C. B.; Naguib, H. E. . Structure to properties relations of BPDA and PMDA backbone hybrid diamine polyimide aerogels . Polymer , 2019 . 176 213 - 226 . .
Jia, M.; Zhou, M.; Li, Y. J.; Lu, G. L.; Huang, X. Y. . Construction of semi-fluorinated polyimides with perfluorocyclobutyl aryl ether-based side chains . Polym. Chem. , 2018 . 9 920 - 930 . DOI: 10.1039/C8PY00004B http://doi.org/10.1039/C8PY00004B .
Qu, L.; Tang, L.; Bei, R.; Zhao, J.; Chi, Z.; Liu, S.; Chen, X.; Aldred, M. P.; Zhang, Y.; Xu, J. . Flexible multifunctional aromatic polyimide film: highly efficient photoluminescence, resistive switching characteristic, and electroluminescence . ACS Appl. Mater. Interfaces , 2018 . 10 11430 - 11435 . DOI: 10.1021/acsami.8b02712 http://doi.org/10.1021/acsami.8b02712 .
Wang, C. Y.; Chen, W. T.; Xu, C.; Zhao, X. Y.; Li, J. . Fluorinated polyimide/POSS hybrid polymers with high solubility and low dielectric constant . Chinese J. Polym. Sci. , 2016 . 34 1363 - 1372 . DOI: 10.1007/s10118-016-1845-x http://doi.org/10.1007/s10118-016-1845-x .
Wang C. Y.; Zhao, X. Y.; Li, G.; Jiang, J. M. . High optical transparency and low dielectric constant of novel soluble polyimides containing fluorine and trifluoromethyl groups . Colloid Polym. Sci. , 2011 . 289 1617 - 1624 . DOI: 10.1007/s00396-011-2471-3 http://doi.org/10.1007/s00396-011-2471-3 .
Liu, Y. W.; Tang, L. S.; Qu, L. J. . Synthesis and properties of high performance functional polyimides containing rigid nonplanar conjugated fluorene moieties . Chinese J. Polym. Sci. , 2019 . 37 416 - 427 . DOI: 10.1007/s10118-019-2225-0 http://doi.org/10.1007/s10118-019-2225-0 .
Yong, W. F.; Li, F. Y.; Chung, T. S.; Tong, Y. W. . Highly permeable chemically modified PIM-1/Matrimid membranes for green hydrogen purification . J. Mater. Chem. A , 2013 . 13914 - 13925 . .
Li, N. B.; Wang, M.; Guo, L. X.; Lin, B. P.; Yang, H. . Ionic liquid embedded polyimides with ultra-foldability, ultra-flexibility, ultra-processability and superior optical transparency . Polymer , 2018 . 153 538 - 547 . DOI: 10.1016/j.polymer.2018.08.048 http://doi.org/10.1016/j.polymer.2018.08.048 .
Wu, Z. L.; Han, B. C.; Zhang, C. H.; Zhu, D. Y.; Gao, L. X.; Ding, M. X.; Yang, Z. H. . Novel soluble and optically active polyimides containing axially asymmetric 9,9′-spirobifluorene units: synthesis, thermal, optical and chiral properties . Polymer , 2012 . 53 5706 - 5716 . DOI: 10.1016/j.polymer.2012.10.024 http://doi.org/10.1016/j.polymer.2012.10.024 .
Genduso, G.; Wang, Y. G.; Ghanem, B. S.; Pinnau, I. . Permeation, sorption, and diffusion of CO 2 -CH 4 mixtures in polymers of intrinsic microporosity: the effect of intrachain rigidity on plasticization resistance . J. Membr. Sci. , 2019 . 584 100 - 109 . DOI: 10.1016/j.memsci.2019.05.014 http://doi.org/10.1016/j.memsci.2019.05.014 .
Wang, C. Y.; Zhao, X. Y.; Li, G. . Synthesis and properties of new fluorinated polyimides derived from an unsymmetrical and noncoplanar diamine . Chin. J. Chem. , 2012 . 30 2466 - 2472 . DOI: 10.1002/cjoc.201200431 http://doi.org/10.1002/cjoc.201200431 .
Wang, C. Y.; Zhao, X. Y.; Li, G. . New soluble polyimides with high optical transparency and light color containing pendant trifluoromethyl and methyl groups . Chin. J. Chem. , 2012 . 30 1555 - 1560 . DOI: 10.1002/cjoc.201100754 http://doi.org/10.1002/cjoc.201100754 .
Ghanem, B. S.; McKeown, N. B.; Budd, P. M.; Selbie, J. D.; Fritsch, D. . High-performance membranes from polyimides with intrinsic microporosity . Adv. Mater. , 2008 . 20 2766 - 2771 . DOI: 10.1002/adma.200702400 http://doi.org/10.1002/adma.200702400 .
Zhang, R.; Li, T. Y.; Zhou, H. B.; Huang, H. H.; Chen, Y. M. . Biobased transparent polyimides with excellent solubility and mechanical properties using myo-inositol derived diamines . React. Funct. Polym. , 2018 . 128 91 - 96 . DOI: 10.1016/j.reactfunctpolym.2018.05.006 http://doi.org/10.1016/j.reactfunctpolym.2018.05.006 .
Wang, C. Y.; Cao, S. J.; Chen, W. T.; Zhao, X. Y.; Li, J.; Ren, Q. . A series of soluble polyimides containing sulfone and trifluoromethyl groups . J. Changzhou Univ. (Natural Science Edition) , 2018 . 30 7 - 12 . .
Wang, C.; Li, G.; Jiang, J. . Novel soluble polyimide containing 4- tert -butyltoluene moiety: synthesis and characterization . Chin. J. Chem. , 2009 . 27 2255 - 2260 . DOI: 10.1002/cjoc.200990378 http://doi.org/10.1002/cjoc.200990378 .
Gan, C. J.; Xu, X. C.; Jiang, X. W. . Fabrication of 6FDA-HFBAPP polyimide asymmetric hollow fiber membranes and their CO 2 /CH 4 separation properties . Chinese J. Polym. Sci. , 2019 . 37 815 - 826 . DOI: 10.1007/s10118-019-2255-7 http://doi.org/10.1007/s10118-019-2255-7 .
Sanaeepur, H.; Ebadi,; Amooghin, A.; Bandehali, S.; Moghadassi, A.; Matsuura, T.; Bruggen, B. V. . Polyimides in membrane gas separation: monomer’s molecular design and structural engineering . Prog. Polym. Sci. , 2019 . 91 80 - 125 . DOI: 10.1016/j.progpolymsci.2019.02.001 http://doi.org/10.1016/j.progpolymsci.2019.02.001 .
Ghanem, B. S.; Swaidan, R.; Litwiller, E.; Pinnau, I. . Ultra-microporous triptycene-based polyimide membranes for high-performance gas separation . Adv. Mater. , 2014 . 26 3688 - 3692 . DOI: 10.1002/adma.201306229 http://doi.org/10.1002/adma.201306229 .
Baker, R. W.; Lokhandwala, K. . Natural gas processing with membranes: an overview . Ind. Eng. Chem. Res. , 2008 . 47 2109 - 2121 . DOI: 10.1021/ie071083w http://doi.org/10.1021/ie071083w .
Sanders, D. F.; Smith, Z. P.; Guo, R.; Robeson, L. M.; Mcgrath, J. E.; Paul, D. R.; Freeman, B. D. . Energy-efficient polymeric gas separation membranes for a sustainable future: a review . Polymer , 2013 . 54 4729 - 4761 . .
Wu, Z.; Yan, G.; Lu, J.; Zhang, G.; Yang, J. . Thermal plastic and optical transparent polyimide derived from isophorone diamine and sulfhydryl compounds . Ind. Eng. Chem. Res. , 2019 . 58 6992 - 7000 . DOI: 10.1021/acs.iecr.9b00674 http://doi.org/10.1021/acs.iecr.9b00674 .
Sulub-Sulub, R.; Loría-Bastarrachea, M. I.; Vázquez-Torres, H.; Santiago-García, J. L.; Aguilar-Vega, M. . Highly permeable polyimide membranes with a structural pyrene containing tert-butyl groups: synthesis, characterization and gas transport . J. Membr. Sci. , 2018 . 563 134 - 141 . DOI: 10.1016/j.memsci.2018.05.054 http://doi.org/10.1016/j.memsci.2018.05.054 .
Qiu, Z. M.; Chen, G.; Zhang, Q. Y.; Zhang, S. B. . Synthesis and gas transport property of polyimide from 2,2′-disubstituted biphenyltetracarboxylic dianhydrides (BPDA) . Eur. Polym. J. , 2007 . 43 194 - 204 . DOI: 10.1016/j.eurpolymj.2006.09.009 http://doi.org/10.1016/j.eurpolymj.2006.09.009 .
Nikiforov, R.; Belov, N.; Zharov, A.; Konovalova, I.; Shklyaruk, B.; Yampolskii, Y. . Gas permeation and diffusion in copolymers of tetrafluoroethylene and hexafluoropropylene: effect of annealing . J. Membr. Sci. , 2017 . 540 129 - 135 . .
Bondi, A. . van der Waals volumes and radii . J. Phys. Chem. , 1964 . 68 441 - 451 . DOI: 10.1021/j100785a001 http://doi.org/10.1021/j100785a001 .
Park, J. Y.; Paul, D. R. . Correlation and prediction of gas permeability in glassy polymer membrane materials via a modified free volume based group contribution method . J. Membr. Sci. , 1997 . 125 23 - 29 . .
Yi, L.; Li, C.; Huang, W. . Soluble polyimides from 4,4′-diaminodiphenyl ether with one or two tert -butyl pedant groups . Polymer , 2015 . 80 67 - 75 . DOI: 10.1016/j.polymer.2015.10.045 http://doi.org/10.1016/j.polymer.2015.10.045 .
Zhao, Q.; Wang, X. Y.; Hu, Y. H. . The application of highly soluble amine-terminated aromatic polyimides with pendent tert -butyl groups as a tougher for epoxy resin . Chinese J. Polym. Sci. , 2015 . 33 1359 - 1372 . DOI: 10.1007/s10118-015-1685-0 http://doi.org/10.1007/s10118-015-1685-0 .
Ishii, J.; Takata, A.; Oami, Y.; Yokota, R.; Vladimirov, L.; Hasegawa, M. . Spontaneous molecular orientation of polyimides induced by thermal imidization (6). Mechanism of negative in-plane CTE generation in non-stretched polyimide membranes . Eur. Polym. J. , 2010 . 46 681 - 693 . DOI: 10.1016/j.eurpolymj.2010.01.007 http://doi.org/10.1016/j.eurpolymj.2010.01.007 .
Qiu, Z. M.; Zhang, S. B. . Synthesis and properties of organosoluble polyimides based on 2,2′-diphenoxy-4,4′,5,5′-biphenyltetracarboxylic dianhydride . Polymer , 2005 . 46 1693 - 1700 . DOI: 10.1016/j.polymer.2004.12.024 http://doi.org/10.1016/j.polymer.2004.12.024 .
Zhang, Q. Y.; Li, S. H.; Li, W. M.; Zhang, S. B. . Synthesis and properties of novel organosoluble polyimides derived from 1,4-bis[4-(3,4-dicarboxylphenoxy)]triptycene dianhydride and various aromatic diamines . Polymer , 2007 . 48 6246 - 6253 . DOI: 10.1016/j.polymer.2007.08.047 http://doi.org/10.1016/j.polymer.2007.08.047 .
Yang, C. P.; Hsiao, S. H.; Chen, K. H. . Organosoluble and optically transparent fluorine-containing polyimides based on 4,4′-bis(4-amino-2-trifluoromethylphenoxy)-3,3′,5,5′-tetramethylbiphenyl . Polymer , 2002 . 43 5095 - 5104 . DOI: 10.1016/S0032-3861(02)00359-2 http://doi.org/10.1016/S0032-3861(02)00359-2 .
Wang, C. Y.; Chen, W. T.; Chen, Y. Y.; Zhao, X. Y.; Li, J.; Ren, Q. . Synthesis and properties of new fluorene-based polyimides containing trifluoromethyl and isopropyl substituents . Mater. Chem. Phys. , 2014 . 144 553 - 559 . DOI: 10.1016/j.matchemphys.2014.01.039 http://doi.org/10.1016/j.matchemphys.2014.01.039 .
Liu, J. T.; Chen, G. F.; Guo, J. C.; Mushtaq, N.; Fang, X. Z. . Synthesis of high performance phenolphthalein-based cardo poly(ether ketone imide)s via aromatic nucleophilic substitution polymerization . Polymer , 2015 . 70 30 - 37 . DOI: 10.1016/j.polymer.2015.05.058 http://doi.org/10.1016/j.polymer.2015.05.058 .
Mo, X.; Wang, C. Y.; Li, G.; Jiang, J. M. . High optical transparency and low dielectric constant polyimides containing trifluoromethyl and cyclohexane groups . J. Macromol. Sci. Phys. , 2011 . 51 1370 - 1383 . .
Yang, C. P.; Hsiao, S. H.; Wu, K. L. . Organosoluble and light-colored fluorinated polyimides derived from 2,3-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic dianhydrides . Polymer , 2003 . 44 7067 - 7078 . DOI: 10.1016/j.polymer.2003.08.032 http://doi.org/10.1016/j.polymer.2003.08.032 .
Yang, C. P.; Hsiao, S. H.; Hsu, M. F. . Organosoluble and light-colored fluorinated polyimides from 4,4′-bis(4-amino-2-trifluoromethylphenoxy) biphenyl and aromatic dianhydrides . Polym. Chem. , 2002 . 40 524 - 534 . DOI: 10.1002/pola.10113 http://doi.org/10.1002/pola.10113 .
Liu, H.; Zhai, L.; Bai, L.; He, M. H.; Wang, C. G.; Mo, S.; Fan, L. . Synthesis and characterization of optically transparent semi-aromatic polyimide films with low fluorine content . Polymer , 2019 . 163 106 - 114 . DOI: 10.1016/j.polymer.2018.12.045 http://doi.org/10.1016/j.polymer.2018.12.045 .
Wang, C.; Cao, S.; Chen, W.; Xu, C.; Zhao, X.; Li, J.; Ren, Q. . Synthesis and properties of fluorinated polyimides with multi-bulky pendant groups . RSC Adv. , 2017 . 7 26420 - 26427 . DOI: 10.1039/C7RA01568B http://doi.org/10.1039/C7RA01568B .
Belov, N.; Chatterjee, R.; Nikiforov, R.; Ryzhikh, V.; Bisoi, S.; Kumar, A. G.; Banerjee, S.; Yampolskii, Y. . New poly(ether imide)s with pendant di- tert -butyl groups: synthesis, characterization and gas transport properties . Sep. Purif. Technol. , 2019 . 217 183 - 194 . DOI: 10.1016/j.seppur.2019.02.017 http://doi.org/10.1016/j.seppur.2019.02.017 .
Dhara, M. G.; Banerjee, S. . Fluorinated high-performance polymers: poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups . Prog. Polym. Sci. , 2010 . 35 1022 - 1077 . DOI: 10.1016/j.progpolymsci.2010.04.003 http://doi.org/10.1016/j.progpolymsci.2010.04.003 .
Barikani, M.; Mehdipour-Ataei, S . Synthesis, characterization, and thermal properties of novel arylene sulfone ether polyimides and polyamides . J. Polym. Sci. Part A: Polym. Chem. , 2000 . 38 1487 - 1492 . DOI: 10.1002/(SICI)1099-0518(20000501)38:9<1487::AID-POLA11>3.0.CO;2-U http://doi.org/10.1002/(SICI)1099-0518(20000501)38:9<1487::AID-POLA11>3.0.CO;2-U .
Wang, C.; Chen, W.; Chen, Y.; Zhao, X.; Li, J.; Ren, Q. . New fluorinated poly(ether sulfone imide)s with high thermal stability and low dielectric constant . Mater. Chem. Phys. , 2014 . 143 773 - 778 . DOI: 10.1016/j.matchemphys.2013.10.012 http://doi.org/10.1016/j.matchemphys.2013.10.012 .
Tian, Z. K.; Cao, B.; Li, P. . Effects of sub- T g cross-linking of triptycene-based polyimides on gas permeation, plasticization resistance and physical aging properties . J. Membr. Sci. , 2018 . 560 87 - 96 . DOI: 10.1016/j.memsci.2018.05.018 http://doi.org/10.1016/j.memsci.2018.05.018 .
Zhang, C.; Li, P.; Cao, B. . Effects of the side groups of the spirobichroman-based diamines on the chain packing and gas separation properties of the polyimides . J. Membr. Sci. , 2017 . 530 176 - 184 . DOI: 10.1016/j.memsci.2017.02.030 http://doi.org/10.1016/j.memsci.2017.02.030 .
Calle, M.; Lozano, A. E.; Abajo, J. D.; Campa, J. G. D.; Álvarez,; C, . Design of gas separation membranes derived of rigid aromatic polyimides. 1. Polymers from diamines containing di- tert -butyl side groups . J. Membr. Sci , 2010 . 365 145 - 153 . DOI: 10.1016/j.memsci.2010.08.051 http://doi.org/10.1016/j.memsci.2010.08.051 .
Zhang, C. L.; Li, P.; Cao, B. . Decarboxylation crosslinking of polyimides with high CO 2 /CH 4 separation performance and plasticization resistance . J. Membr. Sci. , 2017 . 528 206 - 216 . DOI: 10.1016/j.memsci.2017.01.008 http://doi.org/10.1016/j.memsci.2017.01.008 .
Jiang, X. W.; Xiao, X.; Xu, X. C. . Effects of non-TR-able codiamines and rearrangement conditions on the chain packing and gas separation performance of thermally rearranged poly(benzoxazole- co -imide) membranes . J. Membr. Sci. , 2018 . 564 605 - 616 . DOI: 10.1016/j.memsci.2018.07.068 http://doi.org/10.1016/j.memsci.2018.07.068 .
Duthie, X.; Kentish, S.; Powell, C.; Nagai, K.; Qiao, G.; Stevens, G. . Operating temperature effects on the plasticization of polyimide gas separation membranes . J. Membr. Sci. , 2007 . 294 40 - 49 . DOI: 10.1016/j.memsci.2007.02.004 http://doi.org/10.1016/j.memsci.2007.02.004 .
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