Soluble Polyimides from a New Dianhydride: 5′‐<i>tert</i>‐Butyl‐<i>m</i>‐terphenyl‐3,4,3″,4″‐tetracarboxylic Acid Dianhydride

García, Carlos Tejerizo; Lozano, Ángel E.; Campa, José G. de la; Abajo, Javier de

doi:10.1002/marc.200350014

Cited by 15 publications

(21 citation statements)

References 17 publications

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“…The values observed for the cardo polyimides were similar to that reported for the polyimide BTPDA-6F [33] indicating that the cardo moieties did not decrease the thermal resistance.…”

Section: Polymers Properties 321 Thermal Propertiessupporting

confidence: 82%

“…Moreover, the polyimides derived from Cardo and TMeCardo were soluble in dichloromethane and pyridine at room temperature. By contrast, the polyimide BTPDA-6F [33] was insoluble in N,N-dimethylformamide, chloroform, dichloromethane or pyridine. Therefore, the existence of cardo moieties, and additionally the presence of orthomethyl groups in TMeMPD, significantly improved the solubility, when compared with the 6F diamine.…”

Section: Solubilitymentioning

confidence: 96%

“…All commercial monomers were sublimated before use. 5′-tert-butyl-m-terphenyl-3,3″,4,4″-tetracarboxylic acid dianhydride (BTPDA) was synthesized according to the procedure previously reported [33]. 9, fluorene (TMeCardo) was synthesized from 2,6-dimethylaniline (Sigma-Aldrich) and 9-fluorenone (SigmaAldrich) in the presence of trifluoromethanesulfonic acid (Sigma-Aldrich), according to the following procedure: 24.6 g (0.203 mol) of 2,6-dimethylaniline were mixed with 25 mL of concentrated hydrochloric acid and 12 mL of water.…”

Section: Experimental 21 Materialsmentioning

confidence: 99%

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Synthesis, characterization and gas separation properties of novel polyimides containing cardo and tert-butyl-m-terphenyl moieties

Bermejo¹,

Álvarez²,

Maya³

et al. 2018

Express Polym. Lett.

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Abstract.A series of aromatic polyimides has been obtained by the reaction of two dianhydrides, the commercial 2,2′-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) and another having a 5′-tert-butyl-m-terphenyl moiety (BTPDA), with several diamines, including two that have a cardo structure (derived from 9H-fluorene), one of them bearing methyl groups ortho to the amino functionalities (TMeCardo). The solubility, and also the thermal, mechanical, and gas separation properties of the corresponding polyimide membranes were evaluated and compared in order to explore the effect of the different groups in the polyimide backbone. The novel polyimides, which were derived from BTPDA and the cardo diamines, showed high thermal stability, excellent solubility in organic solvents and good gas separation properties, especially the polyimide that bore the ortho methyl substituents. The behavior was especially good for the pair O 2 /N 2 , where the TMeCardo polymer overpassed the Robeson upper bound.

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“…The values observed for the cardo polyimides were similar to that reported for the polyimide BTPDA-6F [33] indicating that the cardo moieties did not decrease the thermal resistance.…”

Section: Polymers Properties 321 Thermal Propertiessupporting

confidence: 82%

Section: Solubilitymentioning

confidence: 96%

Section: Experimental 21 Materialsmentioning

confidence: 99%

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Synthesis, characterization and gas separation properties of novel polyimides containing cardo and tert-butyl-m-terphenyl moieties

Bermejo¹,

Álvarez²,

Maya³

et al. 2018

Express Polym. Lett.

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“…Scheme exhibits the synthetic route of two dianhydrides 7 and 8 with tert ‐butyls by de Abajo and coworkers . The dianhydride 7 was synthesized by Friedel–Crafts reaction, oxidation, and cyclodehydration, while the dianhydride 8 was synthesized through Suzuki coupling reaction, oxidation and cyclodehydration.…”

Section: Synthesis Of Polyimides With Various Side Groupsmentioning

confidence: 99%

“…This can be attributed to the low thermal stability of pyridinyl and linear alkyls themselves. Exceptionally, the introduction of tert ‐butyl just slightly decreased the thermal stability of polyimides and most of them are stable up to 450 °C . In addition, we found the number of tert ‐butyl affect the T g of polyimides, for example, polyimides prepared from diamnie 14 containing two tert ‐butyls displayed higher T g than that of those prepared from diamine 13 containing one tert ‐butyl .…”

Section: The Effects Of Side Groups On Physical Properties Of Polyimidesmentioning

confidence: 99%

Polyimides with side groups: Synthesis and effects of side groups on their properties

Lee

Huang

Yan

2016

J. Polym. Sci. Part A: Polym. Chem.

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Polyimides are a class of well‐known high‐performance polymers combined the excellent mechanical, electrical, and thermal properties and widely applied in many high‐tech fields. Traditional polyimides can only be processed in the state of soluble intermediates with a hazardous step of cyclodehydration and elimination of a nonvolatile polar solvent. Therefore, a great effort has been devoted to the development of soluble polyimides that can be processed in the full imidation state. The incorporation of side groups into the polyimide backbone is an efficient approach to resolve above problems with a little sacrifice of its inherent merits. The subtle variation of side groups in polyimide backbones has allowed researchers to tune their final properties. In particular, some special side groups can endow polyimides the specific property or functionality to broaden their application fields. In this article, we summarize the synthesis of polyimides with side groups in recent 20 years and further discuss the effect of side groups on their physical and specific properties. The future research directions of polyimides with side groups are also discussed. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 533–559

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New, organo‐soluble, thermally stable aromatic polyimides and poly(amide‐imide) based on 2‐[5‐(3,5‐dinitrophenyl)‐1,3, 4‐oxadiazole‐2‐yl]pyridine

Mansoori

Atghia

Sanaei

et al. 2012

Polymer International

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New, thermally stable polyimides and a poly(amide‐imide) containing a 1,3,4‐oxadiazole‐2‐pyridyl pendant group based on 2‐[5‐(3,5‐diaminophenyl)‐1,3,4‐oxadiazole‐2‐yl]pyridine were synthesized. The synthesis and characterization of the model compound 2‐{5‐[(3,5‐bistrimellitimido)phenyl]‐1,3,4‐oxadiazole‐2‐yl}pyridine (DIDA) were also investigated, and DIDA was used in the preparation of the poly(amide‐imide) in an ionic liquid, 1‐butyl‐3‐methylimidazolium bromide, as a polymerization solvent. The polymers were characterized by separating and characterizing the poly(amic acid) intermediates using infrared and elemental analyses. The prepared polymers were soluble in polar and aprotic solvents, such as dimethylformamide, dimethylsulfoxide, N‐methyl‐2‐pyrrolidone and dimethylacetamide. Thermal behaviour of the polymers was studied using thermogravimetric analysis and differential scanning calorimetry. The inherent viscosities of the polyimide and poly(amide‐imide) solutions were in the range 0.34–0.85 dL g−1 (in concentrated sulfuric acid with a concentration of 0.125 g dL−1 at 25 ± 0.5 °C). The removal of Co(II) from aqueous solutions was performed using one of the polyimides. It was found that this polymer had a maximum adsorption capacity and efficiency at pH = 10.0. Copyright © 2012 Society of Chemical Industry

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Soluble Polyimides from a New Dianhydride: 5′‐tert‐Butyl‐m‐terphenyl‐3,4,3″,4″‐tetracarboxylic Acid Dianhydride

Cited by 15 publications

References 17 publications

Synthesis, characterization and gas separation properties of novel polyimides containing cardo and tert-butyl-m-terphenyl moieties

Synthesis, characterization and gas separation properties of novel polyimides containing cardo and tert-butyl-m-terphenyl moieties

Polyimides with side groups: Synthesis and effects of side groups on their properties

New, organo‐soluble, thermally stable aromatic polyimides and poly(amide‐imide) based on 2‐[5‐(3,5‐dinitrophenyl)‐1,3, 4‐oxadiazole‐2‐yl]pyridine

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