Synthesis and properties of new aromatic polyimides containing spirocyclic structures

Terraza, Claudio A.; Tagle, L. H.; Santiago-García, José Luis; Canto-Acosta, R.J.; Aguilar‐Vega, Manuel; Hauyon, René A.; Coll, Deysma; Ortiz, Pablo; Pérez, Germán; Herrán, L.; Comesaña-Gándara, Bibiana; McKeown, Neil B.; Tundidor‐Camba, Alain

doi:10.1016/j.polymer.2018.01.013

Cited by 31 publications

(21 citation statements)

References 24 publications

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“…However, the selectivity of these poly(imide)s decreased as the gas permeability increased. Such behaviour has already been reported in previous works [ 19 , 37 ]. In Table 5 , data available for Matrimid, a commercial poly(imide) membrane, was incorporated for comparison [ 3 ].…”

Section: Resultssupporting

confidence: 88%

New Poly(imide)s Bearing Alkyl Side-Chains: A Study on the Impact of Size and Shape of Lateral Groups on Thermal, Mechanical, and Gas Transport Properties

Rodríguez-González

Pérez²,

Niebla

et al. 2020

Membranes

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A set of five new aromatic poly(imide)s (PIs) incorporating pendant acyclic alkyl moieties were synthesized. The difference among them was the length and bulkiness of the pendant group, which comprises of linear alkyl chains from three to six carbon atoms, and a tert-butyl moiety. The effect of the side group length on the physical, thermal, mechanical, and gas transport properties was analyzed. All PIs exhibited low to moderate molecular weights (Mn ranged between 27.930–58.970 Da, and Mw ranged between 41.760–81.310 Da), good solubility in aprotic polar solvents, except for PI-t-4, which had a tert-butyl moiety and was soluble even in chloroform. This behaviour was probably due to the most significant bulkiness of the side group that increased the interchain distance, which was corroborated by the X-ray technique (PI-t-4 showed two d-spacing values: 5.1 and 14.3 Å). Pure gas permeabilities for several gases were reported (PI-3 (Barrer): He(52); H2(46); O2(5.4); N2(1.2); CH4(1.1); CO2(23); PI-t-4 (Barrer): He(139); H2(136); O2(16.7); N2(3.3); CH4(2.3); CO2(75); PI-5 (Barrer): He(44); H2(42); O2(5.9); N2(1.4); CH4(1.2); CO2(27); PI-6 (Barrer): He(45); H2(43); O2(6.7); N2(1.7); CH4(1.7); CO2(32)). Consistent higher volume in the side group was shown to yield the highest gas permeability. All poly(imide)s exhibited high thermal stability with 10% weight loss degradation temperature between 448–468 °C and glass transition temperature between 240–270 °C. The values associated to the tensile strength (45–87 MPa), elongation at break (3.2–11.98%), and tensile modulus (1.43–2.19 GPa) were those expected for aromatic poly(imide)s.

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Section: Resultssupporting

confidence: 88%

New Poly(imide)s Bearing Alkyl Side-Chains: A Study on the Impact of Size and Shape of Lateral Groups on Thermal, Mechanical, and Gas Transport Properties

Rodríguez-González

Pérez²,

Niebla

et al. 2020

Membranes

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“…Thus, PI-F has the highest value due to the rigidity of the –C(CF 3 ) 2 – moiety in comparison to –O– and –SO 2 –. This behavior has been reported for poly(imides) that contain a dianhydride with –C(CF 3 ) 2 – groups in their structures [45,46,47,48,49]. According to the high thermal stability and T g values showed for all PIs, the new materials would be suitable for application at high-temperature, by including proton exchange membrane.…”

Section: Resultssupporting

confidence: 68%

Synthesis and Properties of Poly(imides) and Poly(imides)/Ionic Liquid Composites Bearing a Benzimidazole Moiety

et al. 2019

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Three new aromatic poly(imides) containing benzimidazole units in the backbone were synthesized and characterized by several spectroscopic techniques. Flexible spacer groups were incorporated into the poly(imides) structure to improve their solubility in organic solvents and their oxidative stabilization. All poly(imides) were thermally stable (Td5% > 512 °C) and had the ability to form dense flexible films. Novel composite films were successfully prepared by loading poly(imide) with ionic liquid ([Bmim]Br) at different concentrations up to 25 wt.%. The resulting materials were characterized according to their morphology and elemental composition (SEM-EDX), water uptake capability, contact angle, and oxidative degradation resistance. Results suggested that poly(imide)/ionic liquid composites would be excellent candidates for future proton conductivity measurements.

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“…The phenol monomer of spirobichroman‐based ( A ) was acquired using bisphenol A and methane sulfonic acid as reagents according to a reported method …”

Section: Methodsmentioning

confidence: 99%

Synthesised spirobichroman‐based polyimide functionalized by pyridine: Effects of substituent position on gas separation and thermal properties

et al. 2019

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Summary Spirobichroman‐based polymers have garnered considerable attention as promising gas separation membrane materials. Herein, two spirobichroman‐based diamines were synthesised using a pyridine heterocyclic ring with methyl substituents at different positions. The diamines were reacted with 4,4′‐(hexafluoroisopropylidene)diphthalic anhydride (6FDA) and bis‐(3‐phthalyl anhydride) ether (ODPA) to achieve four polyimides functionalised by pyridine. The polymers performances were characterised by experimentally and molecular dynamics simulations. They showed high molecular weights of Mn = 9.4 to 14.0 × 104, excellent thermal stability, good solubility in a series of common organic solvents, and easy processability to form membranes. The membrane showed high gas pair selectivities of αCO2/CH4>30 and αCO2/N2>24, which were attributed to turnstile‐like rotary motions of the methyl and basic group of pyridine. The gas permeability results suggested that the substituents position of the methyl has little effect on the rigid molecular chain, unlike the densely packed flexible molecules chains.

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Synthesis and properties of new aromatic polyimides containing spirocyclic structures

Cited by 31 publications

References 24 publications

New Poly(imide)s Bearing Alkyl Side-Chains: A Study on the Impact of Size and Shape of Lateral Groups on Thermal, Mechanical, and Gas Transport Properties

New Poly(imide)s Bearing Alkyl Side-Chains: A Study on the Impact of Size and Shape of Lateral Groups on Thermal, Mechanical, and Gas Transport Properties

Synthesis and Properties of Poly(imides) and Poly(imides)/Ionic Liquid Composites Bearing a Benzimidazole Moiety

Synthesised spirobichroman‐based polyimide functionalized by pyridine: Effects of substituent position on gas separation and thermal properties

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