Citation: Feng Bao, Cheng Liu, Yuan-yuan Song, Zuo-qiang Wu, Jin-yan Wang, Xi-gao Jian. Synthesis of Phthalazinone-containing Poly(aryl-ether-ketone) Block Copolymers with Good Solubility and High Thermal Stability[J]. Acta Polymerica Sinica, ;2018, 0(6): 692-699. doi: 10.11777/j.issn1000-3304.2017.17265 shu

Synthesis of Phthalazinone-containing Poly(aryl-ether-ketone) Block Copolymers with Good Solubility and High Thermal Stability

Feng Bao ¹ ,
Cheng Liu ^1,2 ,
Yuan-yuan Song ¹ ,
Zuo-qiang Wu ¹ ,
Jin-yan Wang ^1,2,, ,
Xi-gao Jian ^1,2,,

Corresponding author: Jin-yan Wang, wangjinyan@dlut.edu.cn Xi-gao Jian, jian4616@dlut.edu.cn
Received Date: 14 September 2017
Revised Date: 9 October 2017
Available Online: 1 March 2018

Through molecular design, three different block copolymers PPENK-b-PEEKK with phthalazinone moiety were synthesized via modest polycondensation reaction from the two macromers PEEKK-OH and PPENK-F. Hydroxy terminated PEEKK-OH macromer was obtained by solution polymerization from HQ and BFBB with sulfolane as the solvent. And the molecular weight of PEEKK-OH was successfully controlled by adjusting the monomer ratio, and the polymerized conditions were optimized by orthogonal experiments. While different molecular weight PPENK-F macromer, endcapped with ―F groups, was prepared from DHPZ, DFK and DFBN. Chemical structures and properties of these block copolymers were inverstigated by Fourier transforming infrared spectrum (FTIR), wide X-ray diffraction (WXRD), differantial scanning calorimetry (DSC) and thermogravimetric analyses (TGA). The FTIR spectra confirmed the formation of the block copolymers. Furthermore, WXRD measurement showed that all the block copolymers presented crystalline structure, and the crystallinity of the coplolymers decreased with increasing molecular weight of PPENK-F chain segments. All the block copolymers showed only one glass transition temperature (T_g), above that of PEEKK-OH. The T_g of the block copolymers increased with the molecular weight of PPENK-F, due to the introduction of PPENK chain segments into the block copolymers. Moreover, for the reason of of PEEKK incorporation, all these copolymers have a same melting point (T_m) of about 340 °C, which would facilitate their thermal processing. Besides, all the three copolymers also exhibited remarkable thermal stability in nitrogen atmosphere with the T_d5% weight loss temperature ranging from 491 °C to 510 °C, and T_d10% from 523 °C to 530 °C, respectively. The char yields of the three copolymers at 800 °C were higher than 63%. Finally, all the copolymers showed improved solubility in selectively tested organic solvents, such as NMP and sulfolane, due to the introduction of twisted and non-coplanar DHPZ structure. Consequently, theses materials are potential candidates for the aerospace applications.
- Phthalazinone,
- Block copolymer,
- Poly(aryl ether),
- Heat-resistant,
- Solubility
1. [1]
  Rose J. Polymer, 1974, 15(7): 456-465 doi: 10.1016/0032-3861(74)90111-6
2. [2]
  Attwood T, Dawson P, Freeman J, Hoy L, Rose J, Staniland P. Polymer, 1981, 22(8): 1096-1103 doi: 10.1016/0032-3861(81)90299-8
3. [3]
  Ke Y C, Fang Z J, Wang J Z, Wu Z W. J Appl Polym Sci, 1996, 61(8): 1293-1303 doi: 10.1002/(ISSN)1097-4628
4. [4]
  Liu T X, Mo Z S, Zhang H F, Na H, Wu Z W. Eur Polym J, 1997,33(6): 913-918 doi: 10.1016/S0014-3057(96)00224-8
5. [5]
  Zimmermann H J, Konnecke K. Polymer, 1991, 32(17): 3162 − 3169 doi: 10.1016/0032-3861(91)90137-8
6. [6]
  Klapper M, Wehrmeister A T, Mullen K. Macromolecules, 1996, (29): 5805-5809
7. [7]
  Meng Y Z, Hay A S, Jian X G, Tjong S C. J Appl Polym Sci, 1998, 68(1): 137-143 doi: 10.1002/(ISSN)1097-4628
8. [8]
  Liu Y J, Jian X G, Liu S J. J Appl Polym Sci, 2001, 82(4): 823-826 doi: 10.1002/(ISSN)1097-4628
9. [9]
10. [10]
11. [11]
  Wang G, Zhang H, Qian B, Wang J, Jian X G, Qiu J. Appl Surf Sci, 2015, 351: 169-174 doi: 10.1016/j.apsusc.2015.05.124
12. [12]
  Zhang S H, Liu P, Chen Y L, Jin J Y, Hu L J, Jian X G. Chem Eng Sci, 2017, (166): 91-100
13. [13]
  Li Y Q, Li T Y, Yan L, Zhang M Y, Zhang Z M. Mater Lett, 2016, (167): 148-152
14. [14]
  Liu R, Wang J Y, Liu C, Li J L, Jian X G. Polym Bull, 2016, 73(7): 1811-1826 doi: 10.1007/s00289-015-1578-y
15. [15]
  Zheng L, Liao G X, Gu T S, Han Y J, Jian X G. Polym Composite, 2009, 30(12): 1842-1847 doi: 10.1002/pc.v30:12
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
  Liu T X, Mo Z S, Zhang H F. Eur Polym J, 1997, 33(6): 913-918 doi: 10.1016/S0014-3057(96)00224-8
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