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

Pérez, Germán; Terraza, Claudio A.; Coll, Deysma; Ortiz, Pablo; Aguilar‐Vega, Manuel; González, Darío M.; Tagle, L. H.; Tundidor‐Camba, Alain

doi:10.1016/j.polymer.2018.12.042

Cited by 6 publications

(13 citation statements)

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“…The results of the NMR characterization also confirmed the chemical structure of each polymer [ 19 , 23 ]. Figure 2 shows the 1 H-NMR spectrum for each poly(imide).…”

Section: Resultsmentioning

confidence: 60%

“…The FT-IR spectra of all monomers showed signals around 3400, 3330 and 1645 cm −1 , associated with the symmetric and asymmetric stretching of the amino (NH 2 ) and amide (NH and C=O) groups, respectively. Additionally, all the 1 H-NMR and 13 C-NMR signals were assigned for each monomer, where the most significant changes in NMR spectra were observed in the aliphatic region due to the different fragments [ 19 ].…”

Section: Resultsmentioning

confidence: 99%

“…The peaks around 1354 and 721 cm −1 correspond to the C-N stretching and the imide rings deformation, respectively. Furthermore, the absorption bands about 3000 cm −1 were ascribed to the C-H stretching of the phenyl and alkyl groups, and the broad signal around 3407 cm −1 was assigned to the N-H stretching of the imide groups [ 19 ]. In addition, no bands associated to the bi-functionality of the used monomers were observed (N-H stretching for diamine at 3388 cm -1 or one of the stretching bands for anhydride (1853 cm −1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Monomers were synthesized following the same procedure described in our previous paper [ 19 ]. Briefly, DNBC reacted with an excess of the corresponding amine (propylamine, butylamine, pentylamine, hexylamine, and tert -butylamine), using THF as solvent and TEA as base.…”

Section: Methodsmentioning

confidence: 99%

“…In previous works, we synthesized a new set of fluorinated aromatic poly(imide)s based on aromatic diamines with various cycloalkyl pendant groups and 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) as a common monomer for all poly(imide)s. Thermal, mechanical, and gas transport properties were studied to evaluate the impact of the volume of C3, C5, C6, C8, and C10 (adamantyl) cyclic lateral groups [ 18 , 19 ]. All poly(imide)s showed similar thermal resistance, reflecting the independency between their overall thermal stability and the bulkiness of the monocyclic pendant groups.…”

Section: Introductionmentioning

confidence: 99%

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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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“…The results of the NMR characterization also confirmed the chemical structure of each polymer [ 19 , 23 ]. Figure 2 shows the 1 H-NMR spectrum for each poly(imide).…”

Section: Resultsmentioning

confidence: 60%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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Intrinsic low‐dielectric‐constant polyimides based on a novel diamine having −CF₃ groups and kinkable 1,4‐diisopropylbenzene units

Nagella,

Park,

Chitumalla

et al. 2023

Polymer International

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Polyimides (PIs) with low dielectric constants and optical transparency are of great interest in 5G/6G communication applications and in the microelectronics industry, where they are used as interlayer dielectric materials, wearable display devices and so forth. In this study, we designed and synthesized a novel fluorinated diamine called 4,4′‐(1,4‐phenylenebis(propane‐2,2‐diyl))diphenoxybis(2‐(trifluoromethyl)‐4‐aminobenzene) (BPBTAB) monomer from bisphenol‐P having diisopropyl benzene units and fabricated four novel BPBTAB‐X PIs. These PI films possess excellent properties such as a low dielectric constant (1.13–1.84 at 1 MHz), high 5% loss temperature (395–491 °C), moderate glass transition temperature (223–254 °C), good tensile modulus (0.827–1.076 GPa), excellent optical properties (T450 up to 83.37%), low moisture absorption (<0.63%) and good solubility in organic solvents. Hence, the as‐synthesized PI films exhibit excellent comprehensive properties for high‐frequency 5G/6G communication applications. © 2023 Society of Chemical Industry.

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Synthesis, optical and dielectric properties of polyacryloyloxy imino fluorophenyl acetamide and polyacryloyloxy imino fluorophenyl acetamide-co-polystyrene sulfonate

2022

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Our scope is synthesis a new poly fluorobenzamide oxime ester and study its structural, optical, and dielectric properties. Consequently, ((E)-2-((acryloyloxy)imino)-N-(4-fluorophenyl) acetamide) (AIFPA) was as-synthesized via a condensation reaction of (E)-N-(4-fluorophenyl)-2-(hydroxyimino) acetamide with acrylic acid to polymerize it via free radical polymerization (PAIFPA). over and above, the synthesized PAIFPA was inserted in more polymerization action with polystyrene sulfonate through the grafting process (PAIFPA-co-PSS). The chemical structures and morphology of AIFPA, PAIFPA, and PAIFPA-co-PSS were characterized by 1H NMR, FTIR, and XRD. The crystallinity index of PAIFPA, and PAIFPA-co-PSS was studied, affording that PAIFPA-co-PSS has the highest crystallinity. Moreover, The optical bandgap that obtained from absorbance analysis was encountered to be in the range of 2.6 eV to 3.5 eV. Ultimately, the dielectric properties of PAIFPA, and PAIFPA-co-PSS showed that electric conductivity values ranged from 6.12 × 10–8 to 7.11 × 10–7 S.cm−1, and 5.48 × 10–10 to 7.75 × 10–8 S.cm−1, respectively. It has a great deal of interest of PAIFPA-co-PSS which has wide band gap energy as short-wavelength light absorbers to be used in tandem polymer solar cells.

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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

Cited by 6 publications

References 19 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

Intrinsic low‐dielectric‐constant polyimides based on a novel diamine having −CF₃ groups and kinkable 1,4‐diisopropylbenzene units

Synthesis, optical and dielectric properties of polyacryloyloxy imino fluorophenyl acetamide and polyacryloyloxy imino fluorophenyl acetamide-co-polystyrene sulfonate

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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

Cited by 6 publications

References 19 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

Intrinsic low‐dielectric‐constant polyimides based on a novel diamine having −CF3 groups and kinkable 1,4‐diisopropylbenzene units

Synthesis, optical and dielectric properties of polyacryloyloxy imino fluorophenyl acetamide and polyacryloyloxy imino fluorophenyl acetamide-co-polystyrene sulfonate

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Intrinsic low‐dielectric‐constant polyimides based on a novel diamine having −CF₃ groups and kinkable 1,4‐diisopropylbenzene units