Abstract
A novel bio-based benzoxazine was synthesized from diphenolic acid and furfurylamine through the facile one-pot formulation method. In comparison with other bio-based thermosetting resins and bio-based benzoxazine resins, the prepared benzoxazine resin had the advantages of accelerated curing behavior, relatively good thermal properties (Tg, 303 °C; char yield (800 °C), 54%), and relatively low superhigh-frequency dielectric constants (2.97 ± 0.01, 5 GHz; 2.95 ± 0.01, 10 GHz; 2.90 ± 0.01, 15 GHz), resulting from the introduction of acidic groups and furan rings. Therefore, this work not only provides a new strategy for the preparation of biomass-based benzoxazine resin with superhigh-frequency low dielectric constants, but also gives some insight into the effects of pentanoic acid and furan rings on the curing behavior, cross-linking structure, and thermal and superhigh-frequency dielectric properties of benzoxazine resin. Furthermore, the potential application of this approach in the advanced superhigh-frequency communication field might make progress towards the sustainable development of high-tech polymeric industry.
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References
M. Zeng, Y.X. Zhou, L.N. Zhang, Polymer 45, 3535 (2004)
M. Rose, R. Palkovits, Macromol. Rapid Commun. 32, 1299 (2011)
Y.Q. Zhu, C. Romain, C.K. Williams, Nature 540, 354 (2016)
Y.W. Huang, M. Zeng, J.B. Chen, Y.Q. Wang, Q.Y. Xu, Mater. Des. 148, 104 (2018)
G. Lligadas, A. Tüzün, J.C. Ronda, M. Galià, V. Cádiz, Polym. Chem. 5, 6636 (2014)
T. Pang, M. Zeng, Z.J. Feng, J.B. Chen, Y.W. Huang, Q.Y. Xu, J. Mater. Sci.: Mater. Electron. 30, 8358 (2019)
Q. Wu, H.M. Wang, C. Yu, W. Hong, IEEE Trans. Antenn. Propag. 67, 2832 (2016)
M. Zeng, J.B. Chen, Q.Y. Xu, Y.W. Huang, Z.J. Feng, Y. Gu, Polym. Chem. 9, 2913 (2018)
H. Ishida, P. Froimowicz, Advanced and Emerging Polybenzoxazine Science and Technology (Elsevier, Amsterdam, 2017)
S.G. Subramaniapillai, J. Chem. Sci. 125, 467 (2013)
T.F. Cummings, J.R. Shelton, J. Org. Chem. 25, 419 (1960)
A. Hariharan, K. Srinivasan, C. Murthy, M. Alagar, Ind. Eng. Chem. Res. 56, 9347 (2017)
E.B. Caldona, A.C.C. De Leon, P.G. Thomas, D.F. Naylor, I.I.I.B.B. Pajarito, R.C. Advincula, Ind. Eng. Chem. Res. 56, 1485 (2017)
Q.Y. Xu, M. Zeng, J.B. Chen, S.G. Zeng, Y.W. Huang, Z.J. Feng, C.J. Yan, Y. Gu, React. Funct. Polym. 122, 158 (2018)
J.Y. Dai, N. Teng, X.B. Shen, Y. Liu, L.J. Cao, J. Zhu, X.Q. Liu, Ind. Eng. Chem. Res. 57, 3091 (2018)
M. Zeng, T. Pang, J.B. Chen, Y.W. Huang, Q.Y. Xu, Y. Gu, J. Mater. Sci.: Mater. Electron. 29, 5391 (2018)
A. Arnebold, O. Schorsch, J. Stelten, A. Hartwig, Polym. Chem. 52, 1693 (2014)
C. Zúñiga, G. Lligadas, J.C. Ronda, M. Galià, V. Cádiz, Polymer 53, 1617 (2012)
C. Zúñiga, M.S. Larrechi, G. Lligadas, J.C. Ronda, M. Galià, V. Cádiz, Polym. Degrad. Stab. 98, 2617 (2013)
H.Q. Yan, C. Sun, Z.P. Fang, X.Q. Liu, J. Zhu, H. Wang, Polymer 97, 418 (2016)
C. Zúñiga, G. Lligadas, J.C. Ronda, M. Galià, V. Cádiz, Polymer 53, 3089 (2012)
R. Ambrožič, U. Šebenik, M. Krajnc, Polymer 76, 203 (2015)
S.P. Teong, G.S. Yi, Y.G. Zhang, Green Chem. 16, 2015 (2014)
P. Thirukumaran, R. Sathiyamoorthi, A.S. Parveen, M. Sarojadevi, Polym. Compos. 37, 573 (2014)
P. Thirukumaran, A.S. Parveen, M. Sarojadevi, ACS Sustain. Chem. Eng. 2, 2790 (2014)
C.F. Wang, C.H. Zhao, J.Q. Sun, S.Q. Huang, X.D. Liu, T. Endo, J. Polym. Sci. A 51, 2016 (2013)
N.K. Sini, J. Bijwe, I.K. Varma, J. Polym. Sci. A 52, 7 (2014)
Y.L. Liu, C.I. Chou, J. Polym. Sci. A 43, 5267 (2005)
Y.L. Liu, C.Y. Chang, C.Y. Hsu, M.C. Tseng, C.I. Chou, J. Polym. Sci. A 48, 4020 (2010)
H. Wang, J. Wang, X. He, T. Feng, N. Ramdani, M. Luan, W. Liu, X. Xu, RSC Adv. 4, 64798 (2014)
L.V. Kotzebue, J. de Oliveira, J. da Silva, E. Mazzetto, H. Ishida, D. Lomonaco, ACS Sustain. Chem. Eng. 6, 5485 (2018)
K. Zhang, M.C. Han, L. Han, H. Ishida, Eur. Polym. J. 116, 526 (2019)
J.Y. Dai, N. Teng, Y.Y. Peng, Y. Liu, L.J. Cao, J. Zhu, X.Q. Liu, Chemsuschem 11, 1 (2018)
X.B. Shen, J.Y. Dai, Y. Liu, X.Q. Liu, J. Zhu, Polymer 122, 258 (2017)
C.H. Lin, C.K. Chien, C.H. Chena, T.Y. Juang, RSC Adv. 7, 37844 (2017)
L. Han, D. Iguchi, P.S. Gil, T.R. Heyl, V.M. Sedwick, C.R. Arza, S. Ohashi, D.J. Lacks, H. Ishida, J. Phys. Chem. A. 121, 6269 (2017)
C.L. Zhu, H.L. Xu, P.F. Geng, Z.J. Lu, High Perform. Polym. 27, 217 (2015)
U. Thubsuang, H. Ishida, S. Wongkasemjit, T. Chaisuwan, Microporous Mesoporous Mater. 156, 7 (2012)
C. Zúñiga, M.S. Larrechi, G. Lligadas, J.C. Ronda, M. Galià, V. Cádiz, J. Polym. Sci. A 49, 1219 (2011)
H. Ishida, T. Agag, Handbook of Benzoxazine Resins (Elsevier, Amsterdam, 2011)
M. Zhang, M. Chen, N. Reddeppa, D.L. Xu, Q.S. Jing, R.H. Zha, Nanoscale 10, 6549 (2018)
Q.Y. Xu, M. Zeng, Z.J. Feng, D. Yin, Y.W. Huang, Y. Chen, C.J. Yan, R.R. Li, Y. Gu, RSC Adv. 6, 31484 (2016)
M.L. Salum, D. Iguchi, C.R. Arza, L. Han, H. Ishida, P. Froimowicz, A.C.S. Sustain, Chem. Eng. 6, 13096 (2018)
M. Zeng, Y.W. Huang, L.Y. Lu, L.R. Fan, D. Lourdin, Carbohydr. Polym. 84, 323 (2011)
Y.W. Huang, M. Zeng, J. Ren, J. Wang, L.R. Fan, Q.Y. Xu, Colloids. Surf. A 401, 97 (2012)
Q.C. Ran, Q. Tian, C. Li, Y. Gu, Polym. Adv. Technol. 21, 170 (2010)
H. Ishida, D.J. Allen, Polymer 37, 4487 (1996)
F.F. Yu, L.W. Cao, Z.H. Meng, N.B. Lin, X.Y. Liu, Polym. Chem. 7, 3913 (2016)
Y. Xu, J. Dai, Q.C. Ran, Y. Gu, Polymer 123, 232 (2017)
D.W. Van Krevelen, Polymer 16, 615 (1975)
M.E. Shabestari, E.N. Kalali, V.J. González, D.Y. Wang, J.P. Fernández-Blázquez, J. Baselga, O. Martin, Carbon 121, 193 (2017)
Y. Fang, X. Zhou, Z. Xing, Y. Wu, J. Appl. Polym. Sci. 134, 44639 (2017)
A. Bereska, P. Kafarski, B. Bereska, B. Tkacz, J. Iłowska, J. Lenża, J. Vinyl Addit. Technol. 23, 142 (2017)
S. Rimdusit, W. Bangsen, P. Kasemsiri, J. Appl. Polym. Sci. 121, 3669 (2011)
B. Patil, B.R.B. Kumar, S. Bontha, V.K. Balla, S. Powar, V.H. Kumar, S.N. Suresha, M. Doddamani, Compos. Sci. Technol. 183, 107816 (2019)
M.T. Jilani, M.Z. Rehman, A.M. Khan, M.T. Khan, S.M. Ali, Int. J. Inform. Technol. Electr. Eng. 1, 1 (2012)
W. Volksen, R.D. Miller, G. Dubois, Chem. Rev. 110, 56 (2010)
J.B. Chen, M. Zeng, Z.J. Feng, T. Pang, Y.W. Huang, Q.Y. Xu, ACS Appl. Polym. Mater. 1, 625 (2019)
S.B. Narang, S. Bahel, J. Ceram. Process. Res. 11, 316 (2010)
C.Y. Lin, J.C. Chiang, C.S. Wang, J. Appl. Polym. Sci. 88, 2607 (2003)
Acknowledgements
This research has been supported by “555” Innovation Team Program (Huaibei) (2019), Anhui Province, PR China, the SRF for ROCS, State Education Ministry (SEM1341), PR China, Hubei Provincial Department of Education (XD2010037), and Engineering Research Center of Nano-Geomaterials of Ministry of Education (CUG2015).
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Digital photos of cured films (Fig. S1); full FTIR spectra of BA, DA, and DF (Fig. S2); full non-isothermal DSC curves of BA, DA, and DF (Fig. S3); FESEM photographs of fracture surfaces of cured films (Fig. S4); TMA curves of PBA, PDA, and PDF (Fig. S5); rough comparison of DF based benzoxazine resin with other bio-based thermosetting resins (Table S1); and rough comparison of DF based benzoxazine with some bio-based benzoxazines (Table S2). Supplementary file1 (DOCX 1388 kb)
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Feng, Z., Zeng, M., Meng, D. et al. A novel bio-based benzoxazine resin with outstanding thermal and superhigh-frequency dielectric properties. J Mater Sci: Mater Electron 31, 4364–4376 (2020). https://doi.org/10.1007/s10854-020-02995-7
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DOI: https://doi.org/10.1007/s10854-020-02995-7