Paper
RSC Advances
due to the similar crystallinity. The tan dmax values gradually
move towards the direction of high temperatures with the
decreases in a,u-diol lengths in each series, suggesting
a gradual increase in Tg values with the increase in rigid
aromatic rings densities.
6 C. Lavilla and S. Munoz-Guerra, Green Chem., 2013, 15, 144–
151.
7 J. Wu, P. Eduard, S. Thiyagarajan, L. Jasinska-Walc,
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F. Fenouillot, A. Rousseau, G. Colomines, R. Saint-Loup and
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possible, renewable nipagin-derived dimethyl esters N1 and N2 10 M. Colonna, C. Berti, M. Fiorini, E. Binassi, M. Mazzacurati,
were prepared via one-step simple nucleophilic substitutions
M. Vannini and S. Karanam, Green Chem., 2011, 13, 2543–
with methyl chloroacetate and 1,4-dibromobutane, respectively.
2548.
Subsequently, two series of aromatic poly(ether ester)s were 11 A. F. Sousa, C. Vilela, A. C. Fonseca, M. Matos, C. S. R. Freire,
prepared from the nipagin-based N1, N2 and linear aliphatic
a,u-diols. The formed poly(ether ester)s exhibit a more than
G. J. M. Gruter, J. F. J. Coelhob and A. J. D. Silvestre, Polym.
Chem., 2015, 6, 5961–5983.
satisfactory resistance to heat with the onset decomposition 12 S. Tomizawa, J. A. Chuah, K. Matsumoto, Y. Doi and
ꢁ
temperature of about 350 C. The incorporation of phenoxy-
K. Numata, ACS Sustainable Chem. Eng., 2014, 2, 1106–1113.
linkages in N1 units has no signicant inuence on the 13 T. Iijima and T. Yamaguchi, Tetrahedron Lett., 2007, 48,
thermal stability of PDN1 with an enhanced T value and the
T5% just decreasing 14 C compared to the DMT-based PDT. The 14 J. Hayashida and V. H. Rawal, Angew. Chem., Int. Ed., 2008,
5309–5311.
d
ꢁ
T
g
values of PN1-us and PN2-us exhibit a tendency to decrease
with the gradual increase in a,u-diol length in their respective 15 W. B. Xu, Q. H. Xu and J. Z. Li, Org. Chem. Front., 2015, 2,
series. The results from differential scanning calorimetry, wide 231–235.
angle X-ray diffraction and isothermal crystallization demon- 16 D. Bledzka, J. Gromadzinska and W. Wasowicz, Environ. Int.,
strate that PN2-us have the higher crystallizabilities than PN1-
2014, 67, 27–42.
us. Additionally, the crystallizability is enhanced with the 17 Y. Guo and K. Kannan, Environ. Sci. Technol., 2013, 47,
gradual increase of a,u-diol length in each series. The nipagin- 14442–14449.
based poly(ether ester)s have excellent mechanical properties 18 N. Cabaleiro, I. de la Calle, C. Bendicho and I. Lavilla, TrAC,
with Young's modulus and tensile strength ranging from 600 to Trends Anal. Chem., 2014, 57, 34–46.
00 MPa and 10 to 35 MPa, respectively. Furthermore, the 19 R. J. Fussell, M. G. Lopez, D. N. Mortimer, S. Wright,
47, 4373–4376.
8
incorporation of phenoxy-linkages has signicantly enhanced
inuence on the toughness of materials by comparing the data
M. Sehnalova, C. J. Sinclair, A. Fernandes and
M. Sharman, J. Agric. Food Chem., 2014, 62, 3651–3659.
of PDN1 with the DMT-based PDT. Due to the high crystalliz- 20 Y. Q. Tian, E. Akiyama and Y. Nagase, J. Mater. Chem., 2003,
ability, PDN2 has the superior thermal stability and mechanical 13, 1253–1258.
properties than PDT. In conclusion, the nipagin-based poly(- 21 J. Y. Lee and J. S. Jang, Polymer, 2006, 47, 3036–3042.
ether ester)s have the potential characteristics that make them 22 L. Wang, Y. H. Wu, W. Zhang and K. Kannan, Environ. Sci.
the excellent structural materials, such as plastic bottles and
medical apparatus and instruments.
Technol., 2013, 47, 2069–2076.
23 A. Maiorana, S. Spinella and R. A. Gross, Biomacromolecules,
2015, 16, 1021–1031.
2
4 D. Fourcade, B. S. Ritter, P. Walter, R. Schonfeld and
R. Mulhaupt, Green Chem., 2013, 15, 910–918.
Acknowledgements
This work was funded by NSFC (51203079), the Natural Science 25 N. Gimeno, R. Martin-Rapun, S. Rodriguez-Conde,
Foundation of Tianjin (14JCYBJC18100), PCSIRT (IRT1257), and
NFFTBS (J1103306).
J. L. Serrano, C. L. Folcia, M. A. Pericas and M. B. Ros, J.
Mater. Chem., 2012, 22, 16791–16800.
2
2
6 J. Frohlich, H. Kautz, R. Thomann, H. Frey and R. Mulhaupt,
Polymer, 2004, 45, 2155–2164.
7 C. Lavilla, A. M. de Ilarduya, A. Alla, M. G. Garcia-Martin,
J. A. Galbis and S. Munoz-Guerra, Macromolecules, 2012,
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