Synthesis and characterization of processable fluorinated aromatic poly(benzamide imide)s derived from cycloalkane substituted diamines, and their application in a computationally driven synthesis methodology

A new set of four fluorinated aromatic poly(benzamide imide)s was synthesized with the objective of preparing condensation polymers with good processability while maintaining high chemical resistance, thermal stability and good mechanical properties. Their synthesis was carried out using commerciall...

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Bibliographic Details
Published in:Polymer (Guilford) 2019-01, Vol.162, p.121-129
Main Authors: Pérez, German, Terraza, Claudio A., Coll, Deysma, Ortiz, Pablo, Aguilar-Vega, Manuel, González, Darío M., Tagle, Luis H., Tundidor-Camba, Alain
Format: Article
Language:English
Subjects:
Anhydrides
Aromatic polyimides
Benzamide
Chemical synthesis
Computation
Computationally driven synthesis methodology
Computer applications
Computer simulation
Condensation polymerization
Cycloalkanes
Diamines
Fluorination
Gas permeation
gas separation membranes
Mechanical properties
Mechanical tests
NMR
Nuclear magnetic resonance
Organic chemistry
Polymers
Stability analysis
Substitutes
Thermal resistance
Thermal stability
X-ray diffraction
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Summary:A new set of four fluorinated aromatic poly(benzamide imide)s was synthesized with the objective of preparing condensation polymers with good processability while maintaining high chemical resistance, thermal stability and good mechanical properties. Their synthesis was carried out using commercially available cycloalkane substituted diamines, 3,5-dinitrbenzoyl chloride and 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) as starting materials. The research was focused on the influence of pendant groups and the testing of a computational methodology that could help to predict polymer properties based on their structure and available QSPR models. To this end, extensive tests were performed on these new poly(imide)s including, IR, NMR, X-ray diffraction, UV absorption, thermal stability, mechanical tests, gas permeation and solubility analyses. The results showed that the materials obtained present properties similar to many available commercial poly(imide)s. On the other hand, computational simulations demonstrated that the strategy followed could be useful in reducing the number of compounds to be synthesized and at the same time, maximize the success ratio of finding polymers with certain desired properties. [Display omitted] •Three new aromatic polyimides containing spirocyclic moieties were obtained and evaluated as gas separation membrane.•The spirocyclic unit is responsible for the good solubility of the polymers.•Bulky rigid components on the polymer backbone are mandatory for attaining high permeability and selectivity.
ISSN:0032-3861
1873-2291
DOI:10.1016/j.polymer.2018.12.042