Synthesis and characterization of poly(arylene ether s‐triazine)s containing alkyl‐, aryl‐ and chloro‐substituted phthalazinone moieties in the main chain

Abstract

Soluble and heat-resistant polymers have great potential for use as processable, high-temperature polymeric materials. In this study, four types of new poly(arylene ether s-triazine)s containing alkyl-, aryl-and chloro-substituted phthalazinone moieties in the main chain were prepared through direct solution polycondensation of 2,4-bis(4-fluorophenyl)-6-phenyl-s-triazine with each of methyl-, phenyl-and chloro-substituted phthalazinones. A key feature of these polymers is the incorporation of phthalazinone and side groups into the poly(arylene ether s-triazine) backbone to endow them with good solubility while maintaining other attractive properties. The polymers were obtained in high yields, and had inherent viscosities ranging from 0.38 to 0.55 dL g −1 . Their structure was characterized using Fourier transform infrared and NMR spectra and elemental analysis. The polymers were almost amorphous, and soluble in N-methyl-2-pyrrolidone, pyridine, N,N-dimethylacetamide, hot N,N-dimethylformamide and sulfolane. Tough and nearly transparent films obtained by direct solution casting exhibited good mechanical properties. The resulting polymers displayed glass transition temperatures ranging from 255 to 265 • C and thermal decomposition temperatures for 10% mass loss ranging from 476 to 599 • C, according to differential scanning calorimetry and thermogravimetric analysis, respectively. The reactivity of substituted phthalazinones in nucleophilic displacement reactions and the effect of the side groups on the physical properties of the polymers were also investigated. The results obtained revealed that such s-triazine-containing polymers possessed good solubility while maintaining acceptable thermal stability and high mechanical strength with the incorporation of alkyl-, aryl-and chloro-substituted phthalazinone moieties into their backbones, which makes them an attractive series of high-performance structural materials.

Effects of phenyl-s-triazine moieties on thermal stability and degradation behavior of aromatic polyether sulfones

“…Among of these newly synthesized polymers, phenyl-striazine polymers have been well-established, in a general sense, as a class of polymeric materials of major academic and industrial importance due to their high performance as well as low cost [5,6]. Additionally, researchers have shown that such polymers exhibit not only a unique combination of properties including organic solvent resistance and chemical corrosion resistance superior to those of state-of-the-art materials but also significantly better elevated temperature behavior [7,8]. Therefore, phenyl-s-triazine polymers have found a variety of applications, such as membranes, coatings, sealants and composite matrixes for elevated temperatures [9,10].…”

“…Incorporation of phenyl-s-triazine units into polymer backbone remarkably enhances the chain rigidity and aromaticity, and polarizable p-electrons of such heterocyclic unit always lead to strong intermolecular interactions. As a result, these materials are always featured by certain fascinating advantages including excellent thermal resistance, good tensile strength and module over those without heterocyclic units [8,9]. Depending on their chemical structure and thermal behavior, phenyl-s-triazine polymers may exist as a thermal plastic or as a thermosetting material [10,11].…”

“…Depending on their chemical structure and thermal behavior, phenyl-s-triazine polymers may exist as a thermal plastic or as a thermosetting material [10,11]. As a class of new emerged thermal plastics, poly(aryl ether phenyl-s-triazine)s (PAEPs) are generally amorphous or semi-crystalline polymers with T g s exceeding 240°C as well as acceptable mechanical properties and good chemical resistance [12][13][14][15][16][17]. PAEPs are normally thought of as one of the most thermally stable polyethers.…”

Synthesis of transparent and thermally stable polycyanurates and their thermal rearrangement

“…Recently, thermally stable and transparent films, whose solubility can be changed by thermal treatment or UV irradiation, were required as described above. Aromatic s ‐triazine‐based polymers have attracted much interest academically and industrially, due to their unique properties, such as excellent thermal resistance, good chemical resistance, and high tensile strengths and moduli . These properties may be attributed to the rigid s ‐triazine units and the strong charge‐transfer interactions between the s ‐triazine rings and the aromatic rings.…”

Synthesis and crosslinking behavior of a soluble, crosslinkable, and high young modulus poly(arylene ether nitriles) with pendant phthalonitriles

“…Recently, many researches focused on improving the solubility of poly(arylene ethers) to expand their widespread application by evolving the incorporation of flexible linkages, kink groups, alkyl pendant groups, or noncoplanar units into the polymer backbones. Besides, introduction of bulky pendant groups into polymer backbone has been recognized as one of the successful approaches to increase the solubility of these high performance polymers 10–13. Meanwhile, to develop polymers for high performance applications, lots of investigations were concentrated on improving the glass transition temperature ( T g ) and the thermal stability via synthesis of oligomers, macromonomers or polymers with terminal CN groups or other activated groups like benzoxazine and epoxy groups.…”