Bio-based adenine-containing high performance polyimide

Hu, Jianghuai; Wang, Zhiping; Zheng, Liang; Chen, Chang; Shi, Meng; Wang, Jianbo; Zhao, Erjin; Zeng, Ke; Ye, Gang

doi:10.1016/j.polymer.2017.05.012

Cited by 52 publications

(38 citation statements)

References 60 publications

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“…At the beginning of imidization reactions, 3290 cm −1 was NH stretching of amide, which shifted to a higher wave number (around 3360 cm −1 ) and weakened with the progressing of imidization for OPI. This phenomenon indicated that imidization process was along with dissolution of H‐bonding derived from NH of amide, as we mentioned above, and 3390 and 3360 cm −1 were assigned to free NH and bonded NH in adenine, respectively . With the progressing of thermal imidization, bonded NH of amide dissociated into free NH, which resulted in strengthening of the peak at around 3360–3390 cm −1 .…”

Section: Resultsmentioning

confidence: 56%

“…In order to analyze the assignment of diffraction peaks, the d ‐spacing values were calculated by Bragg's equation:

n normalλ = 2 d sin normalθ

where n = 1 and λ = 1.54 Å. The calculated d ‐spacing of 5.46 Å (16.22°) and 3.73 Å (24.37°) were corresponding to ch‐packs and π–π stacks . The two intermolecular interaction were stronger than amorphous‐leading peak and rarely moved once they formed at 150°C.…”

Section: Resultsmentioning

confidence: 99%

“…The adenine‐containing diamine p ‐APA was synthesized according to our previous literature (Scheme ). The p ‐APA was dried in a vacuum at 100°C for 6 h before use.…”

Section: Methodsmentioning

confidence: 99%

“…Although introducing adenine block as side and end group was reported, there were rarely papers introducing adenine block to maintain of polymers . Our lab has successfully introduced adenine into mainchain of PI, which exhibited numerous excellent properties such as high glass transition temperature ( T g ) and negative in‐plane coefficient of thermal expansion . The hydrogen of secondary amine and unique ring structure even provide strong potential to transfer protons .…”

Section: Introductionmentioning

confidence: 99%

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The retarding effects and structural evolution of a bio‐based high‐performance polyimide during thermal imidization

Zheng

Liu

et al. 2018

J of Applied Polymer Sci

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The thermal imidization evolution of a bio-based high-performance polyimide, namely adenine-containing polyimide (API), was investigated by thermogravimetric analysis (TGA), in situ Fourier transform infrared spectroscopy (in situ FTIR), and wide-angle X-ray diffraction (WAXD), in contrast to an adenine-free 4,4 0 -oxydiphthalic anhydride (ODPA)/4,4 0 -oxydianiline (ODA) PI. The influence derived from adenine was focused. At precursor stage of API (polyamic acid, PAA), the H-bonding interaction of PAA-PAA type as well as the especial interaction between the secondary amine of adenine and solvent (dimethylacetamide, DMAc) was discovered. Structural evolution of API was traced by in situ FTIR and multistage WAXD from PAA stage to PI stage. Compared with OPI, the retarding effects were found in the process of thermal imidization of API, partly due to the formation of H-bonding derived from the extra secondary amine of adenine moieties, which complicated the H-bonding form in API. Finally, a hypothesis of evolution of thermal imidization process about API molecule was proposed in contrast with adenine-free ODPA ODA PI. Compared with the consistency of both API and ODPA ODA PI in PAA stage, API possessed a more delicate thermal imidization process.

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Section: Resultsmentioning

confidence: 56%

“…In order to analyze the assignment of diffraction peaks, the d ‐spacing values were calculated by Bragg's equation:

n normalλ = 2 d sin normalθ

Section: Resultsmentioning

confidence: 99%

“…The adenine‐containing diamine p ‐APA was synthesized according to our previous literature (Scheme ). The p ‐APA was dried in a vacuum at 100°C for 6 h before use.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The retarding effects and structural evolution of a bio‐based high‐performance polyimide during thermal imidization

Zheng

Liu

et al. 2018

J of Applied Polymer Sci

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“…On the other hand, only limited examples of bio-based difunctional monomers such as diamines and diisocyanates suitable for synthesis of aromatic polyimides are available in the literature [6,9,11,[27][28][29][30][31][32][33][34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of partially bio-based polyimides based on biphenylene-containing diisocyanate derived from vanillic acid

Kuhire

Ichake

Grau

et al. 2018

European Polymer Journal

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A new bio-based biphenylene-containing diisocyanate, namely, 5,5'-diisocyanato-2,2',3,3'-tetramethoxy-1,1'-biphenyl (BDI) was synthesized starting from vanillic acid-a lignin-derived phenolic acid. A series of new partially bio-based polyimides was prepared by polycondensation of BDI with five commercially available aromatic dianhydrides. Polyimides exhibited good solubility in organic solvents and medium molecular weights (Mn (GPC, polystyrene standard) = 25,100-32,200 g mol-1). Polyimides showed good thermal stability with 10 % degradation temperature and glass transition temperature in the range 459-473 °C and 262-329 °C, respectively.

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Dicyanoimidazole resin with bisphenol A moiety: Synthesis, processing, properties, and composites

Zhu

et al. 2022

J of Applied Polymer Sci

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Developing high-performance polymer (HPP) with improved properties by green processing method is one of the core parts of HPP research. In this paper, a new monomer (4,4 0 -((propane-2,2-diylbis(4,1-phenylene))bis(oxy)) dibenzaldehyde (PBhDCI)) of high-performance aromatic nitrile-based (AN) resins with good solubility in ethanol was designed. The rheological analysis showed that PBhDCI is suitable for the processing by laminating process.The cured resins and the corresponding carbon fiber reinforced plastics (CFRP) showed outstanding thermal and mechanical properties. The thermal decomposition temperature (T 5% ) of the cured PBhDCI under nitrogen up to 510 C, the glass transition temperature (T g ) of both resin matrix and CFRP exceeds 500 C, and the flexural strength and modulus of CFRP were 507 ± 5 MPa and 59 ± 2 GPa. This work will offer some guidance for the preparation of high-performance resins and corresponding CFRP with a green processing and high thermal and mechanical properties.

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Bio-based adenine-containing high performance polyimide

Cited by 52 publications

References 60 publications

The retarding effects and structural evolution of a bio‐based high‐performance polyimide during thermal imidization

The retarding effects and structural evolution of a bio‐based high‐performance polyimide during thermal imidization

Synthesis and characterization of partially bio-based polyimides based on biphenylene-containing diisocyanate derived from vanillic acid

Dicyanoimidazole resin with bisphenol A moiety: Synthesis, processing, properties, and composites

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