Synthesis and Properties of Novel Aromatic Copolyamides Derived from 2-(4-carboxyphenyl)-4-[3-phenyl-4-(4-carboxyphenoxyl) phenyl]-phthalazinone

Abstract

A series of four novel aromatic copolyamides were synthesized by the direct polycondensation of 2-(4-carboxyphenyl)-4-[3-phenyl-4-(4-carboxyphenoxyl)phenyl]-phthalazinone (1) and terephthalic acid (TPA) with some commercial diamines. The inherent viscosities of the polyamides were between 0.91 and 2.77 dL g 11 . All the copolyamides showed an amorphous nature as evidenced by wide-angle X-ray diffraction. Introduction of the non-coplanar phthalazinone segments into the polymer main chains remarkably improved the solubility of aromatic copolyamides. Most of the copolymers were soluble in aprotic polar solvents, such as N-methyl-pyrrolidone (NMP), N,N-dimethylacetamide, and dimethylsulfoxide. These aromatic copolyamides showed high thermal properties associated with the glass transition temperatures (T g ) in the range of 261-307 2 C and 10% weight loss temperatures in N 2 over 481 2 C. Moreover, the T g values of the copolyamides increased with the increasing ratio of phthalazinone moiety in the main chain. Some polymer films cast from NMP solution had tensile strengths up to 244.4 MPa, initial moduli up to 5.08 GPa, and elongation at break values up to 9.9%.

Low‐Temperature Solid‐State Microwave Reduction of Graphene Oxide for Transparent Electrically Conductive Coatings on Flexible Polydimethylsiloxane (PDMS)

“…Moreover, the significantly increased thermal stability, shown by the thermal gravimetric analysis (TGA) measurements in Figure 4, also suggests a successful removal of decorating groups and a reduced level of defects on the GO sheets. The onset point ( T d,onset ) of thermal degradation of the materials obtained from TGA measurement is usually considered as an index of the thermal stability of their chemical structures 32–33. Compared to as‐prepared GO ( T d , onset =184 °C), GO reduced by MWs in the solid state shows a significantly increased T d , onset value (629 °C after 240 second and 686 °C after 360 seconds), indicating a successful re‐construction of a fine network from conjugated sp 2 carbon atoms, which has a lower defects level and a higher thermal stability.…”

Phthalonitrile-functional multiple arylene ether nitrile-containing phthalazinone moiety: facile synthesis, curing, and properties

“…4-(4-Hydroxylphenyl)(2H)-phthalazin-1-one (compound 1) was synthesized according to the procedure reported previously. 6,7 2,6-Difluorobenzonitrile (compound 2) and 4-nitrophthalonitrile (compound 3) were purchased from Aldrich Chemical Co. (Shanghai, China), and bis(4-aminophenyl)sulfone (compound 5) was purchased from Acros Organics (Beijing, China) and used as received. Toluene and dimethyl sulfoxide (DMSO) were distilled from calcium hydride under reduced pressure and stored over Linde molecular sieves type 4 Å (Qingdao, China) in a sealed brown bottle.…”

“…4,5 It has been generally recognized that the incorporation of the crank and twisted noncoplanar phthalazinone into rigid-rod polymers leads to a substantial improvement in solubility and certain processing advantages. 6,7 Our group has recently demonstrated the syntheses of poly(phthalazinone ether)s (PPEs) with improved solubility in selected polar solvents. 8,9 Such polymers can be easily prepared in organic solutions and cast into films enabling applications such as membranes and coatings.…”

Synthesis and characterization of new aromatic copoly(ether amide)s bearing 4-trifluoromethylphenyl-2,6-diphenylpyridyl moieties in the main chain

“…31,32 It is well known that copolymerization of rigid plus flexible monomers has been considered as an effective approach to obtain copolyamides with excellent comprehensive properties to meet specific processing and other requirements. [33][34][35] Although many excellent polyamides are known and commercially available, new polyamides are continuing to appear as researchers continue to conduct fundamental studies on chemical structure/property relationships and search for polyamides with unique combination properties for special applications. Based on the wellestablished knowledge of the polyamides containing ether linkage, trifluoromethyl and pyridine groups, we assume that it may be a worthwhile research to develop new polyamides with excellent comprehensive properties by introducing the above functional groups into the molecular skeletons simultaneously.…”