Novel thermally stable poly(sulfone ether ester imide)s

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Abstract

A novel sulfone ether ester diamine was prepared by a three-step method. Reaction of 1,5-dihydroxy naphthalene with 4-nitrobenzoyl chloride afforded 5-hydroxy-1-naphthyl-4-nitrobenzoate. Reduction of nitro group by iron powder and HCl resulted in preparation of 5-hydroxyl-1-naphthyl-4-aminobenzoate. Reaction of this compound (two moles) with bis (4-chlorophenyl) sulfone led to preparation of a novel sulfone ether ester diamine. Three novel aromatic poly(sulfone ether ester imide)s were synthesized by polycondensation reactions of the prepared diamine with aromatic dianhydrides. Conventional methods were used to characterize the structure of the monomer and polymers. Physical properties of the polymers were also studied. The polyimides showed high thermal stability.

Introduction

Aromatic polyimides are thermally stable polymers that generally exhibit excellent mechanical strength and stability and outstanding thermal and oxidative stability. Due to the increased performance characteristics demanded on polymers in various fields including the automobile, aerospace, and electronic industries, the use of these aromatic polymers is growing steadily and they are of major commercial and industrial importance [1].

However, one of the drawbacks to the employment of these polymers is the difficulty in processing due to their insoluble nature in organic solvents in addition to their high melting temperatures or high glass transition temperatures [2].

Therefore, the applications of the majority of polyimides are limited because of their infusibility and insolubility. Thus, for the processing of polyimides many copolyimides, such as poly(amide-imide)s, poly(sulfone-imide)s, poly(ether-imide)s, poly(ester-imide)s and other copolymers have been prepared [3], [4], [5], [6], [7].

Aromatic polymers that contain aryl ether or aryl sulfone linkages generally have lower glass transition temperatures, greater chain flexibility and tractability than their corresponding polymers without these groups in the chain [8], [9].

Polymers containing both aryl ether and aryl sulfone linkages are amorphous, have low glass transition temperatures, and show excellent mechanical properties [10], [11], [12], [13], [14]. The lower glass transition temperatures and also improved solubility are attributed to the flexible linkages that provide a polymer chain with a lower energy of internal rotation [15].

Nowadays, poly(phenylene ether sulfone)s have been developed into commercial products due to their excellent thermo-oxidative stability, mechanical properties, and outstanding hydrolytic stability and recently many reports have been conducted in this field [16], [17], [18], [19]. The present article deals with the synthesis and characterization of novel sulfone ether ester diamine. Aromatic poly(sulfone ether ester imide)s were prepared via reaction of this diamine with aromatic dianhydrides including pyromellitic dianhydride (PMDA), benzophenonetetracarboxylic dianhydride (BTDA), and hexafluoroisopropylidene diphthalic anhydride (6FDA). The polyimides were fully characterized and their physical properties were studied.

Section snippets

Materials

All needed chemicals were purchased either from Merck or Aldrich Chemical Co. Bis(4-chlorophenyl) sulfone was recrystallized from aqueous ethanol. N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), and toluene were vacuum distilled over calcium hydride. Dianhydrides were dried in a vacuum oven at 120 °C overnight.

Instruments

Infrared measurements were performed on a Bruker-IFS 48 FTIR spectrometer (Ettlingen, Germany). The H-NMR spectra were recorded in DMSO-d6 solution using a Bruker Avance DPX

Results and discussion

Aromatic diamines are valuable building blocks for the preparation of variety of polymers including polyimides, polyamides, polyureas, and so on. To extend the utility of high performance polyimides it has been a long desired goal to synthesize diamines, which afford soluble and processable polyimides without too much sacrificing thermal stability. In this way, a novel sulfone ether ester diamine was designed and prepared in three steps. First, nucleophilic reaction of 1,5-dihydroxy naphthalene

Conclusions

A novel sulfone ether ester diamine was prepared and characterized via three-step reactions: Reaction of 4-nitrobenzoyl chloride with 1,5-dihydroxy naphthalene resulted in preparation of 5-hydroxy-1-naphthyl-4-nitrobenzoate (HNNB). Reduction of the nitro group in HNNB afforded 5-hydroxyl-1-naphthyl-4-aminobenzoate (HNAB). HNAB was reacted with bis(4-chlorophenyl) sulfone and thus, a novel sulfone ether ester diamine (SEED) as a building block for preparation of polyimides was synthesized.

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