Synthesis and characterization of poly(amide-imide)s derived from a new <i>ortho</i>-functional unsymmetrical dicarboxylic acid

Canto-Acosta, R.J.; Loría‐Bastarrachea, María Isabel; Carrillo-Escalante, Hugo Joel; Hernández‐Núñez, Emanuel; Aguilar‐Vega, Manuel; Santiago-García, José Luis

doi:10.1039/c7ra11710h

Cited by 15 publications

(9 citation statements)

References 35 publications

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“…Besides, with the sulfonation, the appearance of an absorption band at 1027 cm −1 represents the symmetric stretching vibration of sulfonate group 29 . In case of neat PAI membranes, the characteristic bands at 3300 and 1660 cm −1 corresponds to N–H stretching and C═O stretching were observed 30 . The symmetric peaks enhancement around 1468 cm −1 attributed to the resonance of benzene ring association with asymmetric stretching.…”

Section: Resultsmentioning

confidence: 97%

Proton conducting membrane based on multifunctional interconnected copolymer containing 4,4′‐diaminodiphenylmethane‐aminoethyl piperazine with sulfonated polyethersulfone membrane for fuel cell application

Karunanithi

Pegu

Balaguru

et al. 2021

J of Applied Polymer Sci

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The facile fabrication of proton exchange membrane (PEM) by intermixing of aminoethylpiperazine monomer (AEP), diamino diphenylmethane (DDM) monomer, and AEP combine with varying compositions of DDM (2, 4, and 6 wt%) copolymer with sulfonated polyethersulfone (SPES) and polyamide‐imide (PAI) polymer matrix for fuel cell applications. The intermixing of AEP@DDM copolymer in the SPES/PAI matrix was confirmed by Fourier transform infrared spectroscopy (FTIR) and X‐ray diffraction spectroscopy (XRD) techniques. The physicochemical performance of fabricated PEM was analyzed by water uptake, ion exchange capacity (IEC), swelling ratio, thermal degradation, hydrolytic degradation, chemical and mechanical properties. The intermixing copolymer (AEP@DDM) has significantly suppressed the thermal and hydrolytic deterioration of the PEM. Furthermore, the PAI had noteworthy to improve the thermal and chemical stability of the membranes significantly. The proton conductivity of the SPES/PAI/AEP@DDM (6%) membrane was found to be 5.68 × 10−4 S cm−1 which is 104% higher than the pristine SPES membrane. Besides, the selectivity of SPES/PAI/DDM (6%) was also enhanced up to 80.34% compared to pristine SPES membrane. The inclusion of AEP@DDM in SPES/PAI enhanced the proton conductivity and contributed to the membrane structure's uniformity, as revealed from morphological studies. The AEP@DDM copolymer modification of SPES/PAI membrane has shown good stability, physicochemical property and can be considered as a promising membrane material for fuel cell application.

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Section: Resultsmentioning

confidence: 97%

Proton conducting membrane based on multifunctional interconnected copolymer containing 4,4′‐diaminodiphenylmethane‐aminoethyl piperazine with sulfonated polyethersulfone membrane for fuel cell application

Karunanithi

Pegu

Balaguru

et al. 2021

J of Applied Polymer Sci

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“…27,28 The three absorption bands around 1612, 1531, and 1487 cm −1 are attributed to the C�C stretching vibration of the multiple aromatic rings. 28,29 In the spectrum of the CP-NH copolymer, a characteristic band is observed at 3398 cm −1 for stretching of the N−H bond. However, this band is absent in the spectra of CP-Tba and CP-Prn, which is indicative that the substitution reaction between the oxindole group of CP-NH and either tert-butyl acetate or acetyl pyrene took place during the copolymer modifications.…”

Section: Resultsmentioning

confidence: 99%

“…Additionally, the bands at 1390, 1095, and 742 cm −1 were attributed to C−N stretching, C−O stretching, and C−N bending vibrations, respectively. 27,29…”

Section: Resultsmentioning

confidence: 99%

Carbon Molecular Sieve Membranes from Multiring Highly Aromatic Functional Copolymers

Ortiz-Espinoza,

Loría-Bastarrachea,

Hernández-Cruz

et al. 2024

ACS Appl. Polym. Mater.

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A linear, highly aromatic, random (50/50 mol %), film-forming copolymer was synthesized by a one-pot, metal-free, superacid-catalyzed reaction of isatin with multiring aromatic compounds aceanthrenequinone and p-terphenyl (CP-NH). The chemical modification of the copolymer by the reaction of the side oxindole groups with 1-(bromoacetyl)pyrene and tert-butyl bromoacetate afforded copolymers containing thermolabile tert-butyl acetate (CP-Tba) and acetyl pyrene (CP-Prn) moieties. The polymers obtained were completely soluble in common organic solvents NMP, DMF, and THF, and flexible transparent films could be cast from the solutions. Spectroscopic characterization corroborated the structure of the copolymers. Nonporous films from the CP-NH copolymer show high thermal resistance with onset of decomposition, T d, above 500 °C. Substitution of tert-butyl acetate and acetyl pyrene groups in the copolymer increases density and diminishes FFV. Pure gas permeability coefficients are larger for CP-NH and lower for CP-Prn in agreement with FFV. A mixed gas permeability test for a binary gas sample CO2/CH4 (10/90 mol %) shows that PCO2 and PCH4 decrease compared to pure gases and also decrease with increasing pressure. Carbon molecular sieve membranes (CMSMs) prepared from film precursors CP-NH, CP-Tba, and CP-Prn at a 600 °C final temperature show at least 1 order of magnitude increase in pure gas permeability and around 2 times increase in selectivity for gas pairs O2/N2, CO2/CH4, and N2/CH4. The tert-butyl acetate and acetyl pyrene substitutions in the copolymer precursor increase gas permeability and increase selectivity in CMS membranes. As a result, the performance of pyrolyzed CP-NH, CP-Tba, and CP-Prn CMS membranes is similar to that of other CMSMs reported in the literature in terms of permeability and selectivity.

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“…With the fast development of the PU market, further improvement of the chemical and physical properties of PU materials will make them meet the increasing demands on high-performance materials and suit a rising number of applications. This can be achieved by the chemical modification of PU with thermally stable chemical motifs such as aromatic polyimides, which are one of the most remarkable structures with respect to their outstanding thermal, mechanical, and electrical properties. − As aromatic polyimides have been used to enhance the thermal properties of various polymer matrices, such as poly(ether imide)s, poly(ester imide)s, and poly(amide imide)s, ,− the incorporation of aromatic polyimides in PU promises the development of thermoplastics, − rigid foams, − and coatings − with significantly enhanced thermal stability and flame retardancy, which is especially important for construction and automotive industries.…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Preparation of Thermally Stable Poly(urethane-imide) Elastomers

Guo

Cristadoro²,

Kleemann³

et al. 2023

ACS Appl. Polym. Mater.

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Polyurethanes (PUs) are widely used in many applications due to their versatile chemical and physical properties. To meet the increasing demands on PU with respect to intrinsic mechanical and thermal properties, they can be modified with thermally stable aromatic imide structures to form poly(urethane imide) (PUI). However, the preparation of PUI materials has been limited by the need for strong polar solvents, which hinder their industrial scale development. In this work, we prepared imide-containing isocyanate-terminated prepolymers via the reaction of polymeric aromatic or aliphatic isocyanates and pyromellitic dianhydride in completely solvent-free conditions. The subsequent PUI elastomers made from these prepolymers exhibited enhanced char formation and stiffness in comparison to the reference elastomers without imide structures, among which the aromatic PUI elastomer shows improved flame retardancy according to the initial cone calorimetry measurement. This work demonstrates the potential use of imide prepolymers in other PU applications where high thermal stability and flame retardancy are required. The solvent-free synthesis also paves a way for the large-scale production of PUI materials.

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Synthesis and characterization of poly(amide-imide)s derived from a new ortho-functional unsymmetrical dicarboxylic acid

Abstract: Herein, we report a new diacid monomer containing an imide ring and a methoxy pendant group, 3-trimellitimido-4-methoxybenzoic acid TMBA, for the preparation of poly(amide-imide)s.

Cited by 15 publications

References 35 publications

Proton conducting membrane based on multifunctional interconnected copolymer containing 4,4′‐diaminodiphenylmethane‐aminoethyl piperazine with sulfonated polyethersulfone membrane for fuel cell application

Proton conducting membrane based on multifunctional interconnected copolymer containing 4,4′‐diaminodiphenylmethane‐aminoethyl piperazine with sulfonated polyethersulfone membrane for fuel cell application

Carbon Molecular Sieve Membranes from Multiring Highly Aromatic Functional Copolymers

Solvent-Free Preparation of Thermally Stable Poly(urethane-imide) Elastomers

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