Partially bio-based polyimides from isohexide-derived diamines

Ji, Xiaodong; Wang, Zikun; Yan, Jia‐Nan; Wang, Zhen

doi:10.1016/j.polymer.2015.07.051

Cited by 43 publications

(37 citation statements)

References 34 publications

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“…Recently, isosorbide‐based polymers including polyesters reported by Caouthar et al, polyamides reported by Juais et al, and polycarbonate reported by Chatti et al, Noordover et al, Lorenzini et al, etc., have been intensively studied due to its intrinsic rigidity, aliphatic, nontoxic, as well as biodegradability. However, few papers have been published about the integration of isosorbide into polyimides except Ji et al, who converted isosorbide into a diamine or diamine dihydrochlorides salt which were directly polycondensed with commercial dianhydrides . The obtained polyimides not only exhibited a high transmittance in the NMP solution but also maintained good thermal and mechanical properties.…”

Section: Introductionmentioning

confidence: 99%

Soluble polyimides containing 1,4:3,6‐dianhydro‐d‐glucidol and fluorinated units: Preparation, characterization, optical, and dielectric properties

Liu

Tian

et al. 2017

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

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Aiming to develop soluble and colorless polyimides, two novel diamines, 2,5-bis(2-trifluoromethyl-4-aminophenoxy)-1,4:3,6-dianhydrosorbitol (2a) and 2,5-bis(2-methyl-4amino-phenoxy)-1,4:3,6-dianhydrosorbitol (2b), were designed and synthesized by the reduction of corresponding dinitro monomer which was obtained via solvent-free melt heating method. Polyimides (PI-(1-5)) containing 1,4:3,6-dianhydro-Dglucidol fragments were prepared from 2a and five kinds of common dianhydrides and PI-6 was synthesized from 2b and 4,4 0 -(hexafluoroisopropylidene)-diphthalic anhydride (6FDA) via a two-step thermal imidization. All the polyimides were readily soluble in common polar solvents and could afford flexible, tough, and transparent films with transparency as high as 87% at 450 nm. Meanwhile, PI-(1-6) exhibited unexpectedly low dielectric constants of 2.02-2.52 at 1 MHz. In addition, analogs PI-7 derived from 2,5-bis(4-amino-phenoxy)-1,4:3,6-dianhydrosorbitol (2c) and 6FDA and PI-8 derived from 4,4 0 -bis(4-amino-2-trifluoromethylphenoxy)biphenyl (2d) and 6FDA were also obtained via a two-step thermal imidization for comparision with PI-(1-6) on aspects of thermal, mechnical, optical, electrical, and morphological properties. The structure-property relationships of PI-(1-8) were discussed in detail.

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Section: Introductionmentioning

confidence: 99%

Soluble polyimides containing 1,4:3,6‐dianhydro‐d‐glucidol and fluorinated units: Preparation, characterization, optical, and dielectric properties

Liu

Tian

et al. 2017

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

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“…The yellowish PI – 3 with the lowest transmittance at 52% might result from the crosslinking of benzophenone C = O groups that was positive to the formation of charge transfer complexes. Versus PI–(1 – 4), the higher transmittance of PI – 5 (85%) could be a result of two aspects: firstly, the existence of bulky hexafluoroisopropyl substituent could effectively weaken the molecular chain stacking and result in the obstruction of the intermolecular charge transfer, second, the lower electro‐contribution ability of cis ‐HBPA residues in HBPADA could weaken the inter‐ and intramolecular charge transfer interactions . The higher transmittance of PI – 2 (82%) than that of PI – 1 (74%) and PI – 4 (70%) had a close relationship with the twisted and flexible ether linkages in 4,4 ′ ‐oxydianiline.…”

Section: Resultsmentioning

confidence: 99%

“…Currently, diamines or dianhydrides containing alicyclic fragments have been favored because their corresponding polyimides possess organic soluble, colorless as well as not worsening thermal and mechanical properties . Hydrogenated bisphenol A (HBPA) is a diol that is derived from the hydrogenation addition of bisphenol A. HBPA owns two isomers including cis ‐HBPA and trans ‐HBPA due to different hydrogenation positions on carbon atoms linked with phenolic hydroxyl groups.…”

Section: Introductionmentioning

confidence: 99%

Transparent and soluble polyimide films containing 4,4′‐isopropylidenedicyclohexanol (Cis‐HBPA) units: Preparation, characterization, thermal, mechanical, and dielectric properties

Liu

Wang

et al. 2018

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

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To develop colorless and soluble polyimide films, cis‐hydrogenated bisphenol A (cis‐HBPA) was successfully separated from HBPA isomers, and two novel monomers containing cis‐HBPA unit, 4,4′‐(4,4′‐isopropenylbicyclohexyloxy) diphthalic anhydride (HBPADA) and 4,4′‐(4,4′‐isopropenylbicyclohexyloxy) dianiline (f) were designed and synthesized. PI–(1 – 5) were achieved from HBPADA and five kinds of aromatic diamines and PI – 6 from HBPADA and semiaromatic diamine f via a two‐step thermal imidization. All the polyimides could afford flexible, tough, and transparent films with transparency as high as 86% at 450 nm. Surprisingly, the polyimides containing cis‐HBPA unit exhibited excellent solubility not only in polar solvents such as N, N‐dimethylacetamide, but also in low boiling solvents such as chloroform and dichloromethane. Additionally, analogues aromatic PI – 7 derived from 4,4′‐(hexafluoroisopropylidene)‐diphthalic anhydride (6FDA) and 2,2‐bis(4‐aminophenyl)hexafluoropropane (e) was obtained for comparison with PI–(1 – 6) on aspects of thermal, mechanical, soluble, optical, electrical, and morphological properties. The structure‐property relationships of PI–(1 – 7) were investigated in detail. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 2115–2128

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“…Ji et al. synthesized a series of partially bio‐based PIs from two isohexide‐derived diamine dihydrochloride salts (2,5‐diamino‐2,5‐dideoxy‐1,4: 3,6‐dianhydrosorbitol (DAIS) dihydrochloride and 2,5‐diamino‐2,5‐dideoxy‐1,4: 3,6‐dianhydroiditol (DAII) dihydrochloride) ( Scheme ) and various dianhydrides via a conventional one‐step method in m ‐cressol using triethylamine as catalyst . The isohexide‐derived PIs exhibited excellent optical transparency and thermal stability ( T g s ranged from 214 to 322 °C).…”

Section: Recent Design Approaches To Prepare Cpismentioning

confidence: 99%

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

Tapaswi

2019

Macro Chemistry & Physics

165

155

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Recently, colorless and transparent plastic substrates with high glass transition temperature and suitable thermo‐mechanical properties are in high demand in optoelectronic device industries, due to their various optical applications. Colorless polyimides (CPIs) exhibit both high thermo‐mechanical stability as well as high transparency that are suitable for optoelectronic applications. The most recent (2010–2018) developments on CPIs, in terms of design and synthesis of new monomers and their effects on the thermo‐optical properties of the obtained CPIs, are reviewed in this article.

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Partially bio-based polyimides from isohexide-derived diamines

Cited by 43 publications

References 34 publications

Soluble polyimides containing 1,4:3,6‐dianhydro‐d‐glucidol and fluorinated units: Preparation, characterization, optical, and dielectric properties

Soluble polyimides containing 1,4:3,6‐dianhydro‐d‐glucidol and fluorinated units: Preparation, characterization, optical, and dielectric properties

Transparent and soluble polyimide films containing 4,4′‐isopropylidenedicyclohexanol (Cis‐HBPA) units: Preparation, characterization, thermal, mechanical, and dielectric properties

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

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