Synthesis and properties of aromatic polyimides derived from 2,2,?3,3?-biphenyltetracarboxylic dianhydride

Tong, Yuping; Huang, Wenxi; Luo, Jun; Ding, Mengxian

doi:10.1002/(sici)1099-0518(19990515)37:10<1425::aid-pola4>3.0.co;2-g

Cited by 57 publications

(64 citation statements)

References 18 publications

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“…Data samples were collected at every picoseconds. In this study, the pressure of system was set to 1.0·10 5 Pa. Nose thermostat [20,21] and Berendsen barostat [22] were applied to control temperature and pressure in constant-NPT MD simulation.…”

Section: Simulation Detailsmentioning

confidence: 99%

“…As for Φ1 (torsion angle of C p -C p between phenyl ring), 3,3',4,4'-BPDA-ODA system has peaks in ±35° and ±135°, but in isomeric 2,2',3,3'-BPDA-ODA system, there are only two peaks located in the ±60°. This result is similar to the plot of relative energy of torsion angles for PI monomers in the same systems obtained by molecular mechanics in the previous study [5]. Higher rotational barrier corresponding to Φ1 in 2,2',3,3'-BPDA-ODA system is responsible for the two symmetrical two peaks in the torsion angle distribution, and eventually results in its higher T g .…”

Section: Torsion Angle Distributionmentioning

confidence: 99%

“…If this motion can be observed, the polymer chain should have sufficient space (more free volume) and can complete this motion in a short time period (less relaxation time, it mainly depends on rigidity of a polymer chain). Nevertheless, these two factors can not be well discussed in the gas state [5,7], so it is necessary to find an appropriate method to investigate them in the bulk state. Yet, molecular dynamics (MD) simulation method provides a proper means to study bulk polymer at molecular scale.…”

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confidence: 99%

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Molecular dynamics simulation on glass transition temperature of isomeric polyimide

Li¹,

Liu²,

Qin³

et al. 2009

Express Polym. Lett.

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It is an abnormal phenomenon that glass transition temperature (Tg) of isomeric polyimide (PI) is higher than its corresponding symmetrical PI. To illustrate this phenomenon at the molecular scale, we applied molecular dynamics method to predict the Tg of PI, which were prepared based on 4,4’-oxydianiline (ODA) and 3,3’,4,4’-biphenyltetracarboxylic dianhydride (3,3’,4,4’-BPDA), and its isomeric system (2,2’,3,3’-BPDA-ODA). Simulation result is consistent with experimental value. Non-bond energy plays an important role in glass transition process, for it has an abrupt change near Tg. The higher free volume fraction of isomeric PI can provide the polymer with more space to obtain segmental motion. However, from the torsion angle distribution calculations, it is shown that the torsion angle of its biphenyl group is constrained. Furthermore, from mean square displacement and vector autocorrelation functions calculations, this group is observed to rotate against other groups in the glassy state, and increases the chain rigidity to a great extent. So the isomeric PI needs much more relaxation time for the segment motion. Therefore, the higher Tg of isomeric PI is mainly attributed to the chain rigidity for the time scale, not the free volume for the space scale

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Section: Simulation Detailsmentioning

confidence: 99%

Section: Torsion Angle Distributionmentioning

confidence: 99%

mentioning

confidence: 99%

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Molecular dynamics simulation on glass transition temperature of isomeric polyimide

Li¹,

Liu²,

Qin³

et al. 2009

Express Polym. Lett.

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“…In this work, a series of aromatic biphenyltetracarboxylic dianhydride isomers including a-BPDA, i-BPDA, and s-BPDA are investigated for their ability to form copolymer with bisphenol A-based benzoxazine resin (BA-a). The three isomers are originally synthesized to provide polyimides with improved solubility [20][21][22]. Curing behaviors, dynamic mechanical properties and thermal stability of the obtained polybenzoxazine copolymers are also reported.…”

Section: Introductionmentioning

confidence: 99%

Characterizations of polybenzoxazine modified with isomeric biphenyltetracarboxylic dianhydrides

Rimdusit¹,

Ramsiri²,

Jubsilp³

et al. 2012

Express Polym. Lett.

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Abstract.A series of polymeric alloying films were prepared from bisphenol A/aniline-based bifunctional benzoxazine resin (BA-a) with three isomeric biphenyltetracarboxylic dianhydrides, i.e., 2,3!,3,4!-biphenyltetra carboxylic dianhydride (a-BPDA), 2,2!,3,3!-biphenyltetracarboxylic dianhydride (i-BPDA), and 3,3!,4,4!-biphenyltetracarboxylic dianhydride (s-BPDA) through fully thermal curing. Chemical structure, thermomechanical property and thermal stability of bisphenol A/aniline type polybenzoxazine (PBA-a) copolymers were evaluated. Their chemical structures analyzed via Fourier transform infrared spectroscopy reveal ester carbonyl linkage formation between hydroxyl group of the PBA-a and anhydride group in the isomeric dianhydride. Glass transition temperatures (T g s) of the dianhydride-modified PBA-a increased with PBA-a"<<"i-BPDA"<"a-BPDA"<"s-BPDA. Degradation temperatures (T d ) of the PBA-a copolymers recorded to be in the range of 365-402°C were significantly higher than that of the neat PBA-a i.e. 334°C. Finally, char yield of the PBA-a copolymers was found to be about 54-57% which is about twofold increase from that of the parent PBA-a.

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“…Moreover, it is also useful in the preparation of high performance polyimides that have been widely employed in many fields such as aerospace, spaceflight, mechanical engineering, chemical engineering, microelectron and so on beacuase of their excellent thermal, oxidative stability and excellent mechanical properties. [1][2][3][4][5] Up to now, many publications in the open literature have been found in synthesis of 3,3',4,4'-biphenyltetracarboxylic anhydride (BPDA), and the classical method for such a synthesis constitutes the reductive coupling reaction, which starts from 4-halogeno-o-phthalic acid salt 6,7 or 4-halogeno-o-phthalic anhydride 8,9 or 4-halogeno-o-phthalic acid ester, 10,11 through a dehalogenation-dimerization reaction in the present of palladium carbon. The oxidative coupling reaction of dimethyl phthalate (DMP) under oxyen pressure in the presence of palladium acetate is another well-known method.…”

mentioning

confidence: 99%

An Efficient Synthetic Method for 3,3',4,4'-Biphenyltetracarboxylic Anhydride

Hu¹,

Lu²,

Liu³

et al. 2009

Bulletin of the Korean Chemical Society

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Synthesis and properties of aromatic polyimides derived from 2,2,?3,3?-biphenyltetracarboxylic dianhydride

Cited by 57 publications

References 18 publications

Molecular dynamics simulation on glass transition temperature of isomeric polyimide

Molecular dynamics simulation on glass transition temperature of isomeric polyimide

Characterizations of polybenzoxazine modified with isomeric biphenyltetracarboxylic dianhydrides

An Efficient Synthetic Method for 3,3',4,4'-Biphenyltetracarboxylic Anhydride

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