Abstract
Polycarbonate diols(PCDLs) with a number average molecular weight(Mn) of 2800 and a narrow polydispersity index(PDI=1.33) were synthesized from dimethyl carbonate(DMC) and 1,4-butanediol(BD) via a two-step process. The influences of the molar ratios of DMC to BD in the feedstock, polycondensation temperature and polycondensation time on the PCDLs preparation were studied. CH3COONa showed the best catalytic performance among the catalysts studied. The highest BD conversion of 73.8% and PCDLs yield of 64.7% were achieved under its optimum reaction conditions. Furthermore, based on the results of 1H NMR, the relationships between the ratio of end groups (—OCH3/—OH) of oligomers, the Mn and chainend constitute of resultant polycarbonates were also investigated. The results indicate that PCDLs can be synthesized when the oligomers mostly bear hydroxyl end groups. In contrast, it was impossible to prepare PCDLs when the oligomers were enriched with methyl carbonate end groups.
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Jeon J. Y., Hwang E. Y., Eo S. C., Lee B. Y., Polym. Sci., Part A: Polym. Chem., 2014, 52(11), 1570
Singh H., Jain A. K., J. Appl. Polym. Sci., 2009, 111(2), 1115
Garcia-Pacios V., Costa V., Colera M., Martin-Martinez J. M., Int. J. Adhes. Adhes., 2010, 30(6), 456
Garcia-Pacios V., Colera M., Iwata Y., Martin-Martinez J. M., Prog. Org. Coat., 2013, 76(12), 1726
Serkis M., Poreba R., Hodan J., Kredatusova J., Spirkova M., J. Appl. Polym. Sci., 2015, 132(42), 42672
Sun J. J., Kuckling D., Polym. Chem., 2016, 7(8), 1642
Qin Y. S., Sheng X. F., Liu S. J., Ren G. J., Wang X. H., Wang F. S., J. CO2 Util., 2015, 11, 3
Liu Y., Ren W. M., He K. K., Zhang W. Z., Li W. B., Wang M., Lu X. B., J. Org. Chem., 2016, 81(19), 8959
Liu Y., Zhou H., Guo J. Z., Ren W. M., Lu X. B., Angew. Chem. Int. Ed., 2017, 56(17), 4862
Coates G. W., Moore D. R., Angew. Chem. Int. Ed., 2004, 43(48), 6618
Anderson C. E., Vagin S. I., Xia W., Jin H., Rieger B., Macromolecules, 2012, 45(17), 6840
Park J. H., Jeon J. Y., Lee J. J., Jang Y., Varghese J. K., Lee B. Y., Macromolecules, 2013, 46(9), 3301
Zhang J., Zhu W. X., Li C.C., Zhang D., Xiao Y. N., Guan G. H., Zheng L.C., RSC Adv., 2015, 5(3), 2213
Zhu W. X., Huang X., Li C. C., Xiao Y. N., Zhang D., Guan G. H., Polym. Int., 2011, 60(7), 1060
Jiang Z. Z., Liu C., Gross R. A., Macromolecules, 2008, 41(13), 4671
Matsumura S., Harai S., Toshima K., Macromol. Chem. Physics, 2000, 201(14), 1632
Xu J.W., Feng E., Song J., J. Appl. Polym. Sci., 2014, 131(5), 39822
Wang Z. Q., Yang X. G., Liu S. Y., Hu J., Zhang H., Wang G. Y., RSC Adv., 2015, 5(106), 87311
Wang Z. Q., Yang X. G., Liu S. Y., Zhang H., Wang G. Y., Chem. Res. Chinese Universities, 2016, 32(3), 512
Pitor P., Gabriel R., Polymer, 2004, 45(10), 3125
Tomita K., Ida H., Polymer, 1975, 16(3), 185
Gowda R. R., Chakraborty D., J. Mol. Catal. A: Chem., 2010, 333(1), 167
Gowda R. R., Chakraborty D., J. Mol. Catal. A: Chem., 2011, 349(2), 86
Li Q., Zhu W. X., Li C.C., Guan G. H, Zhang D., Xiao Y. N., Zheng L.C., Polym. Sci., Part A: Polym. Chem., 2013, 51(6), 1387
Zhang T. J., Yang X. G., Li J. G., Hu Y., Wang G. Y., Acta Polym. Sin., 2012, (1), 63
Jofre-Reche J. A., Garcia-Pacios V., Costa V., Colera M., Martin-Martinez J. M., Prog. Org. Coat., 2015, 88, 199
Liu N., Zhao Y. H., Kang M. Q., Wang J. W., Wang X. K., Feng Y. L., Yin N., Li Q. F., Prog. Org. Coat., 2015, 82, 46
Spirkova M., Poreba R., Pavlicevic J., Kobera L., Baldrian J., Pekarek M., J. Appl. Polym. Sci., 2012, 126(3), 1016
Jiang Z. Z., Liu C., Xie W. C., Gross R. A., Macromolecules, 2007, 40(22), 7934
Foy E., Farrell J. B., Higginbotham C. L., J. Appl. Polym. Sci., 2009, 111(1), 217
Wang Z. Q., Yang X. G., Li J. G., Liu S. Y., Wang G. Y., J. Mol. Catal. A: Chem., 2016, 424, 77
Naik P. U., Refes K., Sadaka F., Brachais C. H., Boni G., Couvercelle J. P., Picquet M., Plasseraud L., Polym. Chem., 2012, 3(6), 1475
Wang J., Zheng L. C., Li C. C., Zhu W. X., Zhang D., Guan G. H., Xiao Y. N., Ind. Eng. Chem. Res., 2012, 51(33), 10785
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Supported by the National Key Research and Development Program, China(No.2018YFB0605804), the Key Research and Innovation Program of Jiangsu Province, China(No.BE2015055), and the Science &Technology Pillar Program in Sichuan Province, China(No.2016GZ0228).
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Song, M., Yang, X. & Wang, G. Synthesis of Polycarbonate Diols(PCDLs) via Two-step Process Using CH3COONa as an Effective Catalyst. Chem. Res. Chin. Univ. 34, 578–583 (2018). https://doi.org/10.1007/s40242-018-7390-0
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DOI: https://doi.org/10.1007/s40242-018-7390-0