Preparation of poly(amino-quinone) by microwave-assisted solid-state polymerization

Abstract

Microwave irradiation was employed to assist the synthesis of poly(amino-quinone) (PAQ) from p-benzoquinone and diamines in solid state. The effects of power, time, and pattern (continuously or intermittently) of microwave irradiation on yield and intrinsic viscosity of PAQs were studied. It is shown that the continuous microwave irradiation at a high power leads to rapid increase of yield and a sudden halt in polymerization afterwards, due to the subsequent loss of volatile reactants at a high reaction temperature. Alternatively, the high-power microwave irradiation is applicable to raising the yield if used intermittently. In contrast, the low-power microwave irradiation favours the way of continuous exposure to ensure sufficient heat for polymerization. In both cases of high and low power, the yield and intrinsic viscosity can be further promoted by prolonging the exposure time. It is found that under a preliminarily optimized condition of intermittent irradiation at 490 W with six sequences of 5 min irradiation followed by 5 min interval, the yield and intrinsic viscosity of PAQ from p-benzoquinone and p-phenylene diamine can reach as high as 83% and 41.9 mL/g, respectively.

Keywords

poly(amino-quinone) / microwave / solid-state reaction

References

[1] KaleemK., ChertokF., ErhanS.. A novel coating based on poly(etheramine-quinone) polymers [J]. Progress in Organic Coatings, 1987, 15: 63-71

[2] HanM. J., HelmsA. B., HuY. Q., NiklesD. E.. Amine-quinone polymers and the protection of iron particles against corrosion [J]. IEEE Transactions on Magnetics, 1999, 35(5): 2763-2765

[3] JinF. L., HanM., ParkS. J.. Fracture and adhesion behaviors of epoxy resins modified with poly(amine-quinone) [J]. Polymer International, 2006, 55(11): 1265-1269

[4] JeyaprabhaC., SathiyanarayananS., PhaniK. L. N., VenkatachariG.. Influence of poly (aminoquinone) on corrosion inhibition of iron in acid media [J]. Applied Surface Science, 2005, 252(4): 966-975

[5] ReddyT. A., MacaioneD., ErhanS.. Quinone-amine polymers: XV. Syntheses and characterization of high-temperature resistant poly(arylamino-quinone)s [J]. Journal of Polymer Science, Part A: Polymer Chemistry, 1994, 32(10): 1977-1982

[6] NithianandamV. S., ErhanS.. Quinone-amine polymers: XVIII. A novel method for the synthesis of poly(alkyl aminoquinone)s [J]. Polymer, 1998, 39(17): 4095-4098

[7] MasiukiewiczA. W.. Electron super-exchange mechanism and the residual mobility of topa quinone in amine oxidases [J]. Abstracts of Papers of the American Chemical Society, National Meeting, 2001, 222: U228-U228

[8] KOMABASHIRI T, TSUJINAKA M, MITANI T. Method of preventing polymer scale deposition: US 4970278 [P]. 1990-11-13.

[9] LiangJ. L., NiklesD. E.. Amine-quinone polyurethanes as binders for metal particle tape [J]. IEEE Transactions on Magnetics, 1993, 29(6): 3649-3651

[10] NithianandamV. S., ErhanS.. Quinone amine polymers: IX. Attempts to synthesize polyamine-enzoquinone polymers using air and oxygen as oxidizing agents [J]. Journal of Applied Polymer Science, 1991, 42(9): 2385-2389

[11] DibattistaJ., SchmidtB. M., PadiasA. B., HallH. K.. Substituent effects on the polycondensation of quinones with aromatic amines to form poly(quinone imine)s [J]. Journal of Polymer Science, Part A: Polymer Chemistry, 2002, 40(1): 43-54

[12] ReddyT. A., ErhanS.. Quinone-amine polymers: XII. Synthesis and characterization of novel polymers from 2-phenylbenzoquinone and aliphatic diamines [J]. Journal of Polymer Science, Part A: Polymer Chemistry, 1994, 32(3): 557-565

[13] SinghN. B., SinghR. J.. Solid-state reaction between p-phenylenediamine and p-benzoquinone [J]. Journal of Solid State Chemistry, 1988, 76: 375-390

[14] LinM., ZhouJ. M., XiaH. P., YangR. F., LinC.. Microwave irradiation promoted synthesis of aryloxy acetic acids [J]. Chemical Research in Chinese Universities, 2004, 20(2): 213-215

[15] LiM., ZhangQ. J., YangJ. W., TongS. L., YangK. E., XiaoF. S., DennisK. P. N., YanY.. An efficient and simple reaction: Solventfree preparation of rosolic acid under microwave irradiation [J]. Chemical Research in Chinese Universities, 2008, 24(3): 385-388

[16] HoogenboomR., WilmsT. F. A., ErdmengerT., SchubertU. S.. Microwave-assisted chemistry: A closer look at heating efficiency [J]. Australian Journal of Chemistry, 2009, 62(3): 236-243

[17] KappeC. O., DallingerD.. The impact of microwave synthesis on drug discovery [J]. Nature Reviews Drug Discovery, 2005, 5(1): 51-63

[18] KappeC. O., LarhedM.. All the rave in microwaves [J]. Angewandte Chemie International Edition, 2005, 44(47): 7666-7669

[19] WannbergJ., ErsmarkK., LarhedM.. Microwaveaccelerated synthesis of protease inhibitors [J]. Topics in Current Chemistry, 2006, 266: 167-198

[20] VouyioukaS. N., KarakatsaniE. K., PapaspyridesC. D.. Solid state polymerization [J]. Progress in Polymer Science, 2005, 30(1): 10-37

[21] LiuL., LiY., LiY., FangY. E.. Rapid N-phthaloylation of chitosan by microwave irradiation [J]. Carbohydrate Polymers, 2004, 57(1): 97-100

[22] LobertM., KohnU., HoogenboomR., SchubertU. S.. Synthesis and microwave assisted polymerization of fluorinated 2-phenyl-2-oxazolines: The fastest 2-oxazoline monomer to date [J]. Chemical Communications, 2008, 12: 1458-1460

[23] HoogenboomR., SchubertU. S.. Microwave-assisted organic and polymer chemistry [J]. Australian Journal of Chemistry, 2009, 62(3): 181-183

[24] NavaladianS., ViswanathanB., VaradarajanT. K., ViswanathR. P.. Microwave-assisted rapid synthesis of anisotropic Ag nanoparticles by solid state transformation [J]. Nanotechnology, 2008, 19: 45603-45609

[25] CoanticS., SubraG., MartinezJ.. Microwave-assisted solid phase peptide synthesis on high loaded resins [J]. International Journal of Peptide Research and Therapeutics, 2008, 14(2): 143-147

[26] Diaz-mochonJ. J., FaraM. A., Sanchez-MartinR. M., BradleyM.. Peptoid dendrimers-microwave-assisted solid-phase synthesis and transfection agent evaluation [J]. Tetrahedron Letters, 2008, 49: 923-926

[27] WiesbrockF., HoogenboomR., SchubertU. S.. Microwave-assisted polymer synthesis: State-of-the-art and future perspectives [J]. Macromolecular Rapid Communications, 2004, 25(20): 1739-1764

[28] StraussC. R., VarmaR. S.. Microwaves in green and sustainable chemistry [J]. Microwave Methods in Organic Synthesis, 2006, 266: 199-231

[29] HoogenboomR., LeenenM. A. M., HuangH. Y., FustinC. A., GohyJ. F., SchubertU. S.. Microwave-assisted synthesis and micellization behavior of soy-based copoly(2-oxazoline)s [J]. Colloid and Polymer Science, 2006, 284(11): 1313-1318

[30] HoogenboomR., SchubertU. S.. Microwave-assisted polymer synthesis: Recent developments in a rapidly expanding field of research [J]. Macromolecular Rapid Communications, 2007, 28(4): 368-386

[31] LeeS. J., SandhuK. S., LimS. T.. Effect of microwave irradiation on crystallinity and pasting viscosity of corn starches different in amylose content [J]. Food Science and Biotechnology, 2007, 16(5): 832-835

[32] IdrisA., AhmedI.. Viscosity behavior of microwave-heated and conventionally heated poly(ether sulfone)/dimethylformamide/lithium bromide polymer solutions [J]. Journal of Applied Polymer Science, 2008, 108(1): 302-307

[33] LobertM., ThijsH. M. L., ErdmengerT., EckardtR., UlbrichtC., HoogenboomR., SchubertU. S.. Synthesis, microwave-assisted polymerization, and polymer properties of fluorinated 2-phenyl-2-oxazolines: A systematic study [J]. Chemistry-A European Journal, 2008, 14(33): 10396-10407

[34] WanJ.-jie.Syntheses and electrochemical properties of poly(amino-quinone)s [D], 2004, Changsha, Central South University

[35] MuralidharanS., RavichandranS., PitchumaniS., PhaniK. L. N.. Poly (amino-quinone)s: A new class of polymers for anticorrosive applications [J]. Journal of Materials Science Letters, 2000, 19(14): 1299-1301

[36] WatanabeS., HayamaK., ParkK. H., KakimotoM., ImaiY.. New microwave-assisted rapid synthesis of polyamides from nylon salts [J]. Die Makromolekulare Chemie, Rapid Communications, 1993, 14(8): 481-484

[37] MallakpourS. E., HajipourA. R., FaghihiK.. Microwave-assisted synthesis of optically active poly(amide-imide)s with benzophenone and L-alanine linkages [J]. European Polymer Journal, 2001, 37(1): 119-124

[38] MallakpourS., KowsariE.. Synthesis and properties of organosoluble and optically active poly(amide-imide)s based on epiclon and (s)-(+)-valine under microwave irradiation [J]. Iranian Polymer Journal, 2005, 14(1): 81-90

[39] MallakpourS. E., HajipourA. R., KhoeeS.. Microwaveassisted polycondensation of 4, 4′-(hexafluoroisopropylidene)-N, N′-bis (phthaloyl-L-leucine) diacid chloride with aromatic diols [J]. Journal of Applied Polymer Science, 2000, 77(13): 3003-3009

[40] GoretzkiC., KrlejA., SteffensC., RitterH.. Green polymer chemistry: Microwave-assisted single-step synthesis of various (meth) acrylamides and poly (meth) acrylamides directly from (meth) acrylic acid and amines [J]. Macromolecular Rapid Communications, 2004, 25(3): 513-516

[41] LiQ. T., YangX. J., ChenW. Q., YiC. F., XuZ. S.. Preparation of poly(amic acid) and polyimide via microwave-assisted polycondensation of aromatic dianhydrides and diamines [J]. Macromolecular Symposia, 2008, 261: 148-156

[42] LuJ., ZhuX., JiS., ZhuJ., ChenZ.. Microwave radiation copolymerization in solid state of maleic anhydride and allylthiourea [J]. Journal of Applied Polymer Science, 1998, 68(10): 1563-1566

[43] BogdalD., PenczekP., PielichowskiJ., ProciakA.. Microwave assisted synthesis, crosslinking, and processing of polymeric materials [J]. Advances in Polymer Science, 2003, 163: 193-264