Synthesis and properties of novel soluble polyamides containing both fluorene or xanthene cardo moieties and fluorinated phenoxy pendant groups

Abstract

A series of novel aromatic polyamides containing both fluorene or xanthene cardo moieties and fluorinated phenoxy pendant groups were synthesized from two fluorinated isophthaloyl chlorides and four diamines containing cardo groups by the low‐temperature solution polycondensation in N,N‐dimethylacetamide (DMAc). The obtained polymers were characterized by different physicochemical techniques. All the polymers were amorphous and readily soluble in many organic solvents such as DMAc, N‐methyl‐2‐pyrrolidinone, N,N‐dimethylformamide, dimethyl sulfoxide, pyridine, and tetrahydrofuran at room temperature. The new fluorinated polyamides had high thermal stability with the glass transition temperatures of 237–259°C, the temperatures at 5% weight loss of 437–476°C in nitrogen. All the polymers formed transparent, strong, and flexible films with tensile strengths of 70.6–87.5 MPa, tensile moduli of 2.23–2.78 GPa, and elongations at break of 5.8–8.7%. These polyamide films had high optical transparency with an ultraviolet–visible absorption cutoff wavelength of 352–368 nm, low dielectric constants of 3.24–3.45 (1 MHz), and lower water absorptions of 1.06–1.43%. POLYM. ENG. SCI., 57:1234–1241, 2017. © 2017 Society of Plastics Engineers

A synthesized semi‐aromatic copolyamaide through synergy of three different kinds of monomers: Toward high transparency, excellent heat resistance and melt flowing property

“…12,13 As well known, the monomers with biphenyl or other large pendant groups are always benefit to improving the heat resistance and inhibiting crystallization of the polymer simultaneously. [14][15][16][17][18] By using this method, the obtained polymer generally has higher glass transition temperatures and good transparency, but the excessively rigid molecular structure always makes them hard to flow, thus organic solvents are always necessary in this system, which makes the preparation process complicated and highly polluting. In order to solve these problems, small asymmetric monomers are expected to be applied into the copolymerization reaction, and final properties of the polymer can be adjusted by the kind and the corresponding content of these monomers.…”

Structural, Optical and Thermal Characterization of Wholly Aromatic Poly(ether amide)s Synthesized by Phosphorylation‐Based Condensation Polymerization

“…Therefore, there have been many efforts to improve the solubility in organic solvents of para-aramids by designing their molecular structures. [20,21] Studies have reported that the solubility of aromatic polyamides can be increased by introducing halogen groups or cyano groups into the phenylene ring. [22][23][24] In addition, the introduction of meta aryl or ether group as a flexible linkage to aromatic polymer backbones can improve the solubility and processability.…”

Synthesis of new fluorinated aromatic poly (ether ketone amide)s containing cardo structures by a heterogeneous palladium‐catalyzed carbonylative polycondensation

“…Very recently, we reported the synthesis of a magnetic nanoparticle‐supported bidentate phosphine palladium (II) complex [Fe 3 O 4 @SiO 2 ‐2P‐PdCl 2 ] and its successful application to the carbonylative polycondensation of aromatic diiodides with ether ketone units, aromatic diamines bearing pyridine groups, and carbon monoxide leading to novel aromatic poly (ether ketone amide)s containing 4‐aryl‐2,6‐diphenylpyridine units . It has been demonstrated that the incorporation of fluorinated groups into polyamide backbones can provide not only enhanced solubility but also improved electrical and dielectric performance . Recently, the synthesis of fluorinated polyamides containing cardo structures has attracted considerable interest because of their excellent combined properties .…”

“…It has been demonstrated that the incorporation of fluorinated groups into polyamide backbones can provide not only enhanced solubility but also improved electrical and dielectric performance . Recently, the synthesis of fluorinated polyamides containing cardo structures has attracted considerable interest because of their excellent combined properties . Bandyopadhyay and Banerjee reported the synthesis of spiro [fluorene‐9,9′‐xanthene] containing fluorinated poly (ether amide)s by polycondensation of 2′,7′‐bis‐[2″‐trifluoromethyl 4″‐(4″‐aminophenyl)phenoxy] spiro [fluorene‐9,9′‐xanthene] with different aromatic diacids .…”