Aromatic polyimides containing cyclopropylamide fragment as pendant group. A study of the balance between solubility and structural rigidity

Tundidor‐Camba, Alain; Terraza, Claudio A.; Tagle, L. H.; Coll, Deysma; Ortiz, Pablo; Pérez, Germán; Jessop, Ignacio A.

doi:10.1007/s13233-017-5029-5

Cited by 13 publications

(13 citation statements)

References 32 publications

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“…All aromatic PEIs had good solubility in common aprotic polar solvents. This behavior could be attributed to their oligomeric nature, the torsional mobility provided by the ether groups, and the presence of bulky CF 3 side‐groups along their backbones, which inhibits the chains packing and, consequently, increases the inter‐chains distance . Probably, the same considerations could be used to explain the solubility behavior observed in THF at r.t.…”

Section: Resultssupporting

confidence: 73%

Oligomeric poly(ether‐imide)s bearing ortho trifluoromethyl groups: Solubility, thermal studies, and optical properties

Jessop

Tagle

Coll

et al. 2018

J of Applied Polymer Sci

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In the development of processable high-temperature materials, six new aromatic poly(imide)s based on diamines containing ortho trifluoromethyl groups, ether linkages and R,R-methylenes moieties (R 5 Me or Ph) and previously reported dianhydrides have been synthesized v ıa polycondensation reactions. All polymers were obtained with good yields, were soluble in a variety of polar aprotic solvents, and exhibited inherent viscosity (h inh ) values between 0.15 and 0.20 dL g 21 , which is indicative of low molecularweight species. Preliminary studies of their physical properties were carried out. The new materials were transparent in the visible region and they exhibited thermal decomposition temperatures ranging from 475 to 545 8C and glass-transition temperatures varying from 288 to 304 8C.

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Section: Resultssupporting

confidence: 73%

Oligomeric poly(ether‐imide)s bearing ortho trifluoromethyl groups: Solubility, thermal studies, and optical properties

Jessop

Tagle

Coll

et al. 2018

J of Applied Polymer Sci

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“…The thermograms had two well-defined stages of weight loss, as shown in the derivative curve (DTGA). The first stage, centered between 445 °C and 458 °C, is related to the decomposition of alkyl chains, while the second stage (550–580 °C) is attributed to the rupture of bonds in the poly(imide) backbone [ 18 , 25 , 26 ].…”

Section: Resultsmentioning

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%

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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“…7,8 Therefore, many researches have been carried out to modify the chemical structure of PIs. 9 –15 The most general strategies to increase solubility and decrease T g of these polymers are the introduction of heterocyclic rings, 16 –18 flexible linkages, 19,20 or bulky pendant in the side or backbone chains of polymers, 21,22 and changing the symmetrical structure by using—meta or—ortho aromatic rings attachments. 23 The existence of bulky groups such as xanthene on the backbone affects polymer matrix orders, reduces the structural rigidity, and intermolecular hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

High-performance polyimides based on pyridine and xanthene pendant groups; synthesis, characterization, photoactivity, thermal, antibacterial, and Cr(VI) ion adsorption properties

Amininasab

Esmaili

Shami

2019

High Performance Polymers

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A group of new polyimides (PIs) containing xanthene bulky groups and heterocyclic pyridine ring were synthesized by polycondensation reaction by using new symmetric and asymmetric diamines with available dianhydrides. The prepared diamines and PIs were characterized by Fourier transform infrared, elemental analysis, and proton nuclear magnetic resonance spectroscopy and carbon nuclear magnetic resonance spectroscopy. The PIs have desirable solubility in common aprotic solvents like dimethyl sulfoxide, N-methyl-2-pyrrolidone, dimethylacetamide, and pyridine as a less polar solvent. The PIs with inherent viscosities in the range of 0.51–0.72 dL/g were amorphous in nature, showed glass transition temperatures ( Tgs) of about 270–300°C, and 10% weight loss at temperatures 384–443°C. They showed fluorescence emission (quantum yield 7–12%) due to the presence of xanthene and pyridine groups in their structure. The prepared PIs showed tensile strength of 81–91 MPa with elongation at break of 19–23%. The antibacterial properties of the PIs against Gram negative and Gram positive bacteria and funguses were investigated. Also, a membrane of PI prepared by electrospinning method was used for the removal of different concentrations of Cr(VI) from aqueous solutions.

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Aromatic polyimides containing cyclopropylamide fragment as pendant group. A study of the balance between solubility and structural rigidity

Cited by 13 publications

References 32 publications

Oligomeric poly(ether‐imide)s bearing ortho trifluoromethyl groups: Solubility, thermal studies, and optical properties

Oligomeric poly(ether‐imide)s bearing ortho trifluoromethyl groups: Solubility, thermal studies, and optical 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

High-performance polyimides based on pyridine and xanthene pendant groups; synthesis, characterization, photoactivity, thermal, antibacterial, and Cr(VI) ion adsorption properties

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