Synthesis and Ring-Opening Polymerization of Cyclic Phenolphthalein Poly(ether ketone ketone) Oligomers

doi:10.3724/SP.J.1095.2014.40063

Chinese Journal of Applied Chemistry

• Full Papers • Previous Articles Next Articles

Synthesis and Ring-Opening Polymerization of Cyclic Phenolphthalein Poly(ether ketone ketone) Oligomers

LU Dandan¹, WANG Zhipeng², WANG Honghua², ZHOU Guangyuan^2,3, CUI Shanzi^1*

(1.School of Chemical Engineering,Changchun University of Technology,Changchun 130012,China;
2.Changchun Institute of Applied Chemistry of Sciences,
Chinese Academy of Sciences,Changchun 130022,China;
3.Changzhou Institute of Energy Storage Meterials & Devices,Changzhou 213002,China)

Received:2014-03-05 Revised:2014-05-11 Published:2014-11-08 Online:2014-11-08
Contact: Shan-Zi CUI

Abstract

Abstract: Under pseudo high dilution conditions, cyclic oligomers of phenolphthalein poly(ether ketone ketone)s(c-PEKK-C) were synthesized from phenolphthalein and 4,4′-difluorotribenzodiketone(DFTBDK) with a cyclization ratio of 78%. MALDI-TOF MS characterization indicates that c-PEKK-C has a broad size distribution(n=2~8) with cyclic dimers and trimers as main components(85%). The molecular structure of DFTBDK is prone to form cyclic structure that can be confirmed by Jacobson-Stockmayer theory. Melt ring-opening polymerization(ROP)(300~350 ℃) of cyclic oligomers catalyzed by potassium 4,4′-biohenol gives the corresponding linear products with high relative molecular mass(Mw 1.2×105).

Key words: aromatic cyclic oligomers, phenolphthalein poly(ether ketone ketone)s, pseudo high dillution technology

CLC Number:

O625.4

LU Dandan1, WANG Zhipeng2, WANG Honghua2, ZHOU Guangyuan2,3, CUI Shanzi1*. Synthesis and Ring-Opening Polymerization of Cyclic Phenolphthalein Poly(ether ketone ketone) Oligomers[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.40063.

References

[1] WANG Honghua,GUO Qingzhong,CHEN Tianlu. Progress in Synthesis of Aromatic Cyclic Oligomers[J]. Prog Chem,2005,17(4):716-721(in Chinese).

王红华,郭庆中,陈天禄. 芳香环状低聚体的制备方法[J]. 化学进展,2005,17(4):716-721.

[2] Li S H. Cyclic Aryl Ketone Oligomers Containing the ISO-Phthaloyl Moiety:Synthesis and Ring-Opening Polymerization[J]. Adv Mater Res,2013,781:411-414.

[3] Shukla D,Negi Y S,Uppadhyaya J S,et al. Synthesis and Modification of Poly(ether ether ketone) and Their Properties:A Review[J]. Polym Rev,2012,52(2):189-228.

[4] Brunelle D J. New Methods of Polymer Synthesis[M]. London:Blackie,1995.

[5] Chen K,Du X S,Meng Y Z,et al. The Preparation and Characterization of Novel Cocylic(arylene disulfide) oligomers[J]. Polym Adv Technol,2003,14(2):114-121.

[6] Bonauto D K,Brunelle D J. Hydroquinone-bisphenol Cyclic Copolycarbonate Oligomer:USPatent 4920200[P]. 1990-4-24.

[7] Hoskins J N,Grayson S M. Cyclic Polyesters: Synthetic Approaches and Potential Applications[J]. Polym Chem,2011,2(2):289-299.

[8] Xu D,Li X,Gao C,et al. Development of an Efficient Route to Hyperbranched Poly(aryl ether ketone)s[J]. High Perform Polym,2012,24(3):188-193.

[9] GUO Qingzhong,CHEN Tianlu. Study on the Relationship Between Aromatic Cyclic Oligomers Distribution and Monomer Structure[J]. Chem J Chinese Univ,2003,24(5):909-912(in Chinese).

郭庆中,陈天禄. 芳香环状低聚物组分分布与单体结构关系的研究[J]. 高等学校化学学报,2003,24(5):909-912.

[10] GUO Qingzhong,XIAO Ying. Characterization of Cyclic(arylene ketone) Oligomers by Matrix- assisted Laser Desorption Ionization Time-of-flight Mass Spectrometry[J]. J Wuhan Inst Technol,2011,33(5):5-7(in Chinese).

郭庆中,肖颖. MALDI-TOF质谱表征芳香环状聚酮低聚物及其组分分布[J]. 武汉工程大学学报,2011,33(5):5-7.

Synthesis and Ring-Opening Polymerization of Cyclic Phenolphthalein Poly(ether ketone ketone) Oligomers

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 3

Recommended Articles

Metrics

Comments

[1]	ZHANG Tianyong, DU Jing, LI Bin*, WANG Xiao. Synthesis of 1,4-Naphthoquinone by Oxidation of 1-Naphthylamine [J]. Chinese Journal of Applied Chemistry, 2013, 30(05): 500-505.
[2]	LIU Changhui, WEN Ruiming*, YE Xiaoqin, YI Xianwen, FANG Lei. Synthesis and Characterization of Ionone-containing Chalcones [J]. Chinese Journal of Applied Chemistry, 2012, 29(07): 780-783.
[3]	ZHANG Xiao-Song, DING Guo-Hua*, QI Qiao-Zhen. Synthesis, Crystal Structure and Spectroscopic Property of [Cu(C₂₀H₁₀Cl₄O₂N₂)]·DMF [J]. Chinese Journal of Applied Chemistry, 2010, 27(11): 1334-1338.