Synthesis and characterization of polyarylene sulfide sulfone/ketone amide

Abstract

High-molecular-weight polyarylene sulfide sulfone amide (PASSA) and polyarylene sulfide ketone amide (PASKA) were synthesized from diamine monomers containing sulfone or ketone group by a low temperature solution polycondensation reaction in anhydrous N-methylpyrrolidone (NMP). The structures of the monomers and corresponding polymers were identified by IR-spectra and UV spectra. The maximum intrinsic viscosities of the polymers were 0.72 dL/g in NMP (PASSA) and 0.62 dL/g in H₂SO₄ (PASKA) at 30±0.1°C, respectively. The polymers possess excellent thermal properties with the glass transition temperature (T_g) for PASSA and PASKA are 274.9°C and 195.2°C, respectively. The initial degradation temperatures (T_i) for PASSA and PASKA are 461.55°C and 467.08°C, respectively, which suggests that PASSA and PASKA are excellent heat-resistant materials. The dissolvability experiments show that PASSA and PASKA are also corrosion resistance materials.

Keywords

polyarylene sulfide sulfone / polyarylene sulfide amine / polyarylene sulfide sulfone amide / polyarylene sulfide ketone amide / 4,4′-bis(4-aminothio phenyl)diphenyl sulfone / 4,4′-bis(4,- aminothiophenyl) diphenyl ketone

References

[1] Yang J, Wang H D, Xu S X. Study on Polymerization Conditions and Structure of Poly(phenylene Sulfide Sulfone). Journal of Polymer Research, 2005, 12: 317-323

[2] Wang H D, Yang J, Long S R. Study on the high performance polymers polyphenylene sulfide sulfone. Polymeric Materials Science and Engineering, 2003, 19(3): 54-57(in Chinese)

[3] Liu Y A, Bhatnagar Q, Ji J S, Riffle J E. McGrath J, Geibel F, Kashiwagi T. Influence of polymerization conditions on the molecular structure stability and physical behavior of poly(phenylene sulfide sulfone) homopolymers. Polymer, 1999, 41: 5137-5146

[4] Zhou Z W, Wu Q X, Chen Y R. Synthesis and characterization of poly(phenylene sulfide amide). Polymeric Materials Science and Engineering, 1992, 5: 26–29 (in Chinese)

[5] Cheng N L. Solvents Handbook. The Chemical Industry Press. 3rd. 2002: 831-833 (in Chinese)

[6] Jpn. kokai, Tokyo Koho,1985, <patent>JP60-188365</patent>

[7] Zhang L L, Jiang L X, Cai X X. Synthesis of aromatic sulfone ether diamine, bismaleimide and the thermal stability of their copolymers. Hecheng Huaxue, 1994, 2(1): 50-56(in Chinese)

[8] Nadia A Mohamed. Novel wholly aromatic polyamide-hydrazides-Iv. Effect of polymers structural compositions on their properties. Eur Polym J, 1995, 31(9): 859-865

[9] Liu P, Wang W B, Zhong Z W, Wang K T, Wang J. Study on synthesis of 4,4′-bis(3-aminophenoxy)diphenyl sulfone. Chemistry and Adhesion, 1998, 4: 209-211(in Chinese)

[10] Tamai S, Ohkawa Y, Yamaguchi. Aromatic thermotropic liquid crystalline polymers from 1.3-bis[4-(4-aminophenoxy)-α dimethylbenzyl]benzene.Polymer, 1997, 38(16): 4079-4084

[11] Nadia A M, Abeer O H. Al-Dossary. Structure–property relationships for novel wholly aromatic polyamide–hydrazides containing various proportions of para-phenylene and meta-phenylene units. European Polymer Journal, 2003, 39: 739-750

[12] Biware M V, Ghatge N D. Studies in piperazine containing poly(sulphone-amide)s for use in water desalination. Desalination, 1995, (101): 93-100

[13] Wing H C, Suei Y L-L. Synthesis and characterization of random poly(amide-sulfonamide)s: 3. Copolymers from two diamino monomers. Polymer, 1995, 36(23): 4503-4508

[14] Seung-Yeop, Kwak. Relationship of relaxation property to reverse osmosis permeability in aromatic polyamide thin-film-composite membranes. Polymer, 1999, 40: 6361-6368

[15] Yang J. Study on the synthesis, structure and performance of high molecular weight polyarylene sulfide sulfone. Degree thesis of Sichuan University, 2005(in Chinese)

[16] Xu SX. Studies on the synthesis and characterization and properties of copoly(Phenylene sulfide sulfone/phenylene sulfide Ketone). Degree thesis of Sichuan University, 2003(in Chinese)

[17] Liu C L, Wang X J, Chen C K, Long S R, Yang J. The synthes is of polyarylene lmide sulfide. Polymeric Materials Science and Engineering, 2007, 23(2): 103-106 (in Chinese)

[18] Dwayne R. Senn. Synthesis characterization of ran–copoly(p-phenylene sulfide sulfone/ketone)s. Polym Sci Part A, 1994, (32): 1175-1183

[19] Durvasula V R, Stuber F A, Bhattacharjee D. Synthesis of polyphenylene ether and thioether ketones. Polym Sci Part A, 1989, 27(2): 661-669

[20] Xu S X, Yang J, Long S R. Synthesis and characterization of poly(p-phenylene sulfide sulfone/ketone) copolymer. Polymer Bulletin, 2005, 54(4-5): 251-261

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