Shan Jiang, Ruhui Shi, Haiyang Cheng, Chao Zhang, Fengyu Zhao. Synthesis of polyurea from 1,6-hexanediamine with CO2 through a two-step polymerization. Green Energy&Environment, 2017, 2(4): 370-376. doi: 10.1016/j.gee.2017.05.001
Citation: Shan Jiang, Ruhui Shi, Haiyang Cheng, Chao Zhang, Fengyu Zhao. Synthesis of polyurea from 1,6-hexanediamine with CO2 through a two-step polymerization. Green Energy&Environment, 2017, 2(4): 370-376. doi: 10.1016/j.gee.2017.05.001

Synthesis of polyurea from 1,6-hexanediamine with CO2 through a two-step polymerization

doi: 10.1016/j.gee.2017.05.001
  • Activation and transformation of CO2 is one of the important issues in the field of green and sustainable chemistry. Herein, CO2 as a carbon-oxygen resource was converted to CO2-polyurea with 1,6-hexanediamine through a two-step polymerization. The reaction parameters such as temperature, pressure and reaction time were examined; and several kinds of catalysts were screened in the absence and presence of NMP solvent. The formed oligomer and the final polyurea were characterized by FT-IR, VT-DRIFTS, NMR, XRD, AFM and their thermal properties were examined by TGA and DSC. It was confirmed that the final polyurea has a high thermal stability; the melting temperature is 269 °C and the decomposition temperature is above 300 °C. It is a brittle polymer with a tensile strength of 18.35 MPa at break length of 1.64%. The polyurea has a stronger solvent resistance due to the ordered hydrogen bond in structure. The average molecular weight should be enhanced in the post-polymerization as the appearance, hydrogen bond intensity, crystallinity, melting point and the thermal stability changed largely compared to the oligomer. The present work provides a new kind of polyurea, it is expected to have a wide application in the field of polymer materials.

     

  • loading
  • [1]
    A.A.Ensafi, H.A.Alinajafi, B.Rezaei J. Electroanal. Chem., 783 (2016),pp. 82-89
    [2]
    S.Xiao, Y.F.Zhang, P.Gao, et al. Catal. Today, 281 (2017),pp. 327-336
    [3]
    C.Zhang, K.W.Jun, R.Gao, et al. Fuel, 190 (2017),pp. 303-311
    [4]
    Z.X.Yang, H.Y.Wang, W.J.Song, et al. J. Colloid Interface Sci., 486 (2017),pp. 232-240
    [5]
    W.Panjan, J.Sirijaraensre, C.Warakulwit, et al. Phys. Chem. Chem. Phys., 14 (2012),pp. 16588-16594
    [6]
    S.Gildemyn, K.Verbeeck, R.Slabbinck, et al. Environ. Sci. Technol. Lett., 2 (2015),pp. 325-328
    [7]
    Q.L.Qian, J.J.Zhang, M.Cui, et al. Nat. Commun., 7 (2016)
    [8]
    K.K.Sakimoto, S.J.Zhang, P.Yang Nano Lett., 16 (2016),pp. 5883-5887
    [9]
    I.Garcia-Herrero, R.M.Cuéllar-Franca, V.M.Enríquez-Gutiérrez, et al. ACS Sustain. Chem. Eng., 4 (2016),pp. 2088-2097
    [10]
    H.J.Kuenen, H.J.Mengers, D.C.Nijmeijer, et al. Comput. Chem. Eng., 86 (2016),pp. 136-147
    [11]
    F.Parrino, C.Deiana, M.R.Chierotti, et al. , 13 (2016),pp. 90-94
    [12]
    M.Aresta, A.Dibenedetto, A.Dutta Catal. Today, 281 (2017),pp. 345-351
    [13]
    R.Srivastava, D.Srinivas, P.Ratnasamy J. Catal., 233 (2005),pp. 1-15
    [14]
    G.L.Gregory, L.M.Jenisch, B.Charles, et al. Macromolecules, 49 (2016),pp. 7165-7169
    [15]
    J.N.Xie, Z.F.Diao, C.Qiao, et al. , 16 (2016),pp. 313-317
    [16]
    A.Polyzos, M.O'Brien, T.P.Petersen, et al. Angew. Chem. Int. Ed., 50 (2011),pp. 1190-1193
    [17]
    M.D.Greenhalgh, S.P.Thomas J. Am. Chem. Soc., 134 (2012),pp. 11900-11903
    [18]
    A.Vigorito, Q.Gou, C.Calabrese, et al. ChemPhysChem, 16 (2015),pp. 2961-2967
    [19]
    Q.H.Ren, N.N.Wu, Y.Cai, et al. Organometallics, 35 (2016),pp. 3932-3938
    [20]
    C.Y.Wu, H.Y.Cheng, R.X.Liu, et al. Green Chem., 12 (2010),pp. 1811-1816
    [21]
    D.L.Sun, J.H.Ye, Y.X.Fang, et al. Ind. Eng. Chem. Res., 55 (2016),pp. 64-70
    [22]
    M.Tamura, K.Ito, Y.Nakagawa, et al. J. Catal., 343 (2016),pp. 75-85
    [23]
    M.Tamura, K.Noro, M.Honda, et al. Green Chem., 15 (2013),pp. 1567-1577
    [24]
    D.J.Darensbourg, F.T.Tsai Macromolecules, 47 (2014),pp. 3806-3813
    [25]
    X.Jiang, F.Gou, H.W.Jing J. Catal., 313 (2014),pp. 159-167
    [26]
    Y.Liu, W.M.Ren, W.P.Zhang, et al. Nat. Commun., 6 (2015),p. 8594
    [27]
    Y.Y.Wang, J.W.Fan, D.J.Darensbourg Angew. Chem. Int. Ed., 54 (2015),pp. 10206-10210
    [28]
    J.Langanke, A.Wolf, J.Hofmann, et al. Green Chem., 16 (2014),pp. 1865-1870
    [29]
    B.Grignard, J.M.Thomassin, S.Gennen, et al. Green Chem., 18 (2016),pp. 2206-2215
    [30]
    Y.Z.Long, F.H.Sun, C.Liu, et al. J. Appl. Polym. Sci., 133 (2016)
    [31]
    L.Poussard, J.Mariage, B.Grignard, et al. Macromolecules, 49 (2016),pp. 2162-2171
    [32]
    C.Y.Wu, J.Y.Wang, P.J.Chang, et al. Phys. Chem. Chem. Phys., 14 (2012),pp. 464-468
    [33]
    Z.Ying, L.J.Zhao, C.Zhang, et al. RSC Adv, 5 (2015),pp. 42095-42100
    [34]
    Z.Ying, Y.Dong, J.Wang, et al. Green Chem., 18 (2016),pp. 2528-2533
    [35]
    Z.Ying, C.Y.Wu, S.Jiang, et al. Green Chem., 18 (2016),pp. 3614-3619
    [36]
    Z.Ying, C.Zhang, S.Jiang, et al. , 15 (2016),pp. 131-135
    [37]
    Y.He, D.L.Xie, X.Y.Zhang J. Mater. Sci., 49 (2014),pp. 7339-7352
    [38]
    H.Shinohara, Y.Takahashi, J.Mizuno, et al. Sens. Actuat. B Chem., 132 (2008),pp. 374-379
    [39]
    S.Q.Li, Z.H.Sang, J.B.Zhao, et al. Ind. Eng. Chem. Res., 55 (2016),pp. 1902-1911
    [40]
    W.C.Pan, C.H.Lin, S.A.Dai J. Polym. Sci. Part A Polym. Chem., 52 (2014),pp. 2781-2790
    [41]
    N.Yamazaki, T.Iguchi, F.Higashi Tetrahedron, 31 (1975),pp. 3031-3034
    [42]
    N.Yamazaki, F.Higashi, T.Iguchi J. Polym. Sci. Part C. Polym. Lett., 12 (1974),pp. 517-521
    [43]
    P.X.Wang, X.Y.Ma, Q.H.Li, et al. RSC Adv., 6 (2016),pp. 54013-54019
    [44]
    F.Y.Zhao, S.Fujita, S.Akihara, et al. J. Phys. Chem. A, 109 (2005),pp. 4419-4424
    [45]
    A.Ion, V.Parvulescu, P.Jacobs, et al. Green Chem., 9 (2007),pp. 158-161
    [46]
    F.Shi, Y.Q.Deng, T.L.SiMa, et al. Angew. Chem. Int. Ed., 42 (2003),pp. 3257-3260
    [47]
    Q. Chu, US20140024800-A1.
    [48]
    A.L.Ingram, T.M.Nickels, D.K.Maraoulaite, et al. Appl. Spectrosc., 71 (2017),pp. 238-249
    [49]
    M.Rozenberg, A.Loewenschuss, Y.Marcus Phys. Chem. Chem. Phys., 2 (2000),pp. 2699-2702
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Article Metrics

    Article views (140) PDF downloads(18) Cited by()
    Proportional views

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return