Synthesis and characterization of fluorinated polyimides derived from novel unsymmetrical diamines

Yang, Fengchun; Li, Yanfeng; Ma, Tao; Bu, Qianqian; Zhang, Shujiang

doi:10.1016/j.jfluchem.2010.03.014

Cited by 21 publications

(11 citation statements)

References 19 publications

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“…As an approach to circumventing this problem, the incorporation of unsymmetrical repeat units into PIs have been recently used to improve their solubility and processibility . For example, the introduction of an unsymmetrical trifluoromethyl group into the polymer chain has resulted in soluble PIs without compromising the properties via the reduction in solubility‐impeding inter‐chain interactions . Aromatic poly(ether‐imides) derived from an unsymmetrical indane‐based diamine have been evaluated for gas permeation properties .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of unsymmetrical benzonitrile‐containing polyimides: Viscosity‐lowering effect and dielectric properties

Wang

Riley

Fillery

et al. 2013

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

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A new unsymmetrical diamine, 2-(3-aminophenoxy)-6-(4-aminophenoxy)benzonitrile (3,4-APBN), is synthesized via two consecutive S N Ar reactions and the temperature-dependent reactivity of the fluorides in 2,6-difluorobenzonitrile, whose first S N Ar reaction occurs at 70 C and second, at 100 C, allowing timing control of reaction sequence and circumventing the transetherification side reaction. Thus, a series of polyimides (PIs) is prepared from the polymerization of 3,4-APBN with five common dianhydrides (6FDA, DSDA, OPDA, BTDA, and PMDA). For comparison, a second series is also prepared from two symmetrical diamines ([2,6-bis(3-aminophenoxy)benzonitrile (3,3-APBN) and 2,6-bis(4-aminophenoxy)benzonitrile (4,4-APBN)] and 6FDA or PMDA. The processability of the poly(amic acids) (PAAs), for the first series is greatly improved since their solution viscosities are much lower than PAAs based on symmetrical diamines. Besides having high glass-transition temperatures (249-332 C), and thermal stability [5% weight loss in the range of 505-542 C (air) and 512-546 C (nitrogen)], these PIs form tough, transparent and flexible films that have a tensile-strength range of 82.1-121.3 MPa, elongations-at-break of 5.33-9.81%, and tensile moduli of 2.11-2.97 GPa. Their film dielectric constants are 3.08-3.62 at 10 kHz, moderately higher than that (2.92) of analogous PI (CP2) without nitrile groups. Overall, we found that the reduction of structural symmetry in repeat units can improve the polymer processibility as well as increasing their dielectric constants.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of unsymmetrical benzonitrile‐containing polyimides: Viscosity‐lowering effect and dielectric properties

Wang

Riley

Fillery

et al. 2013

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

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“…other merits such as good thermal and low moisture absorption [25][26][27]. Carbon nanotubes (CNTs) with high stiffness and tensile strength have received enormous attention for the composites with desired mechanical properties [28], and also in electrochemistry mainly due to their electrocatalytic effects and ability to promote electron transfer reactions [29].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of trifluoromethylated poly(ether–imidazole–imide)s based on unsymmetrical diamine bearing carbazole and imidazole chromophores in ionic liquids: Study of electrochemical properties by using nanocomposite electrode

Ghaemy

Hassanzadeh

Taghavi

et al. 2012

Journal of Fluorine Chemistry

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“…Polyimide materials usually exhibit higher moisture uptake than the hydrocarbon polymers due to the presence of imide groups 28. The moisture uptake of aromatic PIs could be up to 3.0–3.5% depending on the chemical structure of polymer and the relative humidity of the environments 12. Thus, the introduction of trifluoromethyl groups, on one hand could inhibit the moisture uptake of the fluorinated PIs due to their hydrophobic features; on the other hand could loosen the packing density of the polymer backbone chains, thus increasing the moisture uptake of the polymers due to its bulky volume.…”

Section: Resultsmentioning

confidence: 99%

“…To overcome these drawbacks, much effort has been focused on the design and synthesis of soluble and processable PIs without sacrificing their prominent thermal stability. Thus, many approaches have been applied to improve their solubility, thermal stability, and processability through introducing flexible aryl‐ether linkages,5–7 noncoplanar structures,8–10 unsymmetrical structures,11–13 or bulky substituents14–16 into the polymer backbone. One of the most successful approaches is to incorporate fluorine‐containing groups,17, 18 especially the trifluoromethyl groups into the polyimide structure 17–27.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of ternary‐copolymer of soluble fluorinated polyimides based on 1,4‐bis (4‐amino‐2‐trifluoromethylphenoxy) benzene

Fang

Zhou

et al. 2012

J of Applied Polymer Sci

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A series of novel ternary-copolymer of fluorinated polyimides (PIs) were prepared from 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene (pBATB), commercially available aromatic dianhydrides, and aromatic diamines via a conventional two-step thermal or chemical imidization method. The structures of all the obtained PIs were characterized with FTIR, 1 H-NMR, and element analysis. Besides, the solubility, thermal stability, mechanical properties, and moisture uptakes of the PIs were investigated. The weight-average molecular weight (M w ) and the number-average molecular weight (M n ) of the PIs were determined using gel-permeation chromatography (GPC). The PIs were readily dissolved not only in polar solvents such as DMF, DMAc, and NMP, but also in some common organic solvents, such as acetic ester, chloroform, and acetone. The glass transition temperatures of these PIs ranged from 201 to 234 C and the 10% weight loss temperatures ranged from 507 to 541 C in nitrogen. Meanwhile, all the PIs left around 50% residual even at 800 C in nitrogen. The GPC results indicated that the PIs possessed moderate-to-high number-average molecular weight (M n ), ranging from 9609 to 17,628. Moreover, the polymer films exhibited good mechanical properties, with elongations at break of 8-21%, tensile strength of 66.5-89.8 MPa, and Young's modulus of 1.04-1.27 GPa, and low moisture uptakes of 0.54-1.13%. These excellent combination properties ensure that the polymer could be considered as potential candidates for photoelectric and microelectronic applications.

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Synthesis and characterization of fluorinated polyimides derived from novel unsymmetrical diamines

Cited by 21 publications

References 19 publications

Synthesis and characterization of unsymmetrical benzonitrile‐containing polyimides: Viscosity‐lowering effect and dielectric properties

Synthesis and characterization of unsymmetrical benzonitrile‐containing polyimides: Viscosity‐lowering effect and dielectric properties

Synthesis and characterization of trifluoromethylated poly(ether–imidazole–imide)s based on unsymmetrical diamine bearing carbazole and imidazole chromophores in ionic liquids: Study of electrochemical properties by using nanocomposite electrode

Synthesis and characterization of ternary‐copolymer of soluble fluorinated polyimides based on 1,4‐bis (4‐amino‐2‐trifluoromethylphenoxy) benzene

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