Synthesis and properties of novel meltable fluorinated aromatic oligoimides endcapped with 4-phenylethynylphthalic anhydride

High Performance Polymers

Volumn 21, Issue 2, 2009, Pages 187-204

  Chen, Jiansheng ^a   Zuo, Hongjun ^a   Fan, Lin ^a   Yang, Shiyong ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

Low viscosity; Oligoimides; Phenylethynyl endcapped; Thermal stability

Indexed keywords

AMINES; AROMATIC COMPOUNDS; BENZENE; CURING; DIFFERENTIAL SCANNING CALORIMETRY; GLASS TRANSITION; MECHANICAL PROPERTIES; MOLECULAR WEIGHT; POLYCONDENSATION; POLYIMIDES; POLYMERS; RESINS; STRENGTH OF MATERIALS; THERMODYNAMIC STABILITY; THERMOSETS; VISCOSITY;

4-PHENYLETHYNYLPHTHALIC ANHYDRIDES; AROMATIC DIAMINES; AROMATIC DIANHYDRIDE; CHEMICAL COMPOSITIONS; ELONGATION AT BREAKS; END-CAPPING; FLEXURAL MODULUS; FLEXURAL STRENGTHS; GLASS TRANSITION TEMPERATURES; LOW VISCOSITY; LOW-VISCOSITY FLUIDS; MELT VISCOSITIES; MELTABILITY; OLIGOIMIDE; OLIGOIMIDES; OXYDIANILINE; OXYDIPHTHALIC ANHYDRIDES; PHENYLETHYNYL-ENDCAPPED; POLYIMIDE RESINS; TEMPERATURE RANGES; THERMAL AND MECHANICAL PROPERTIES; THERMAL POLYCONDENSATION; THERMAL STABILITY;

AROMATIZATION;

EID: 62449299036     PISSN: 09540083     EISSN: 13616412     Source Type: Journal    
DOI: 10.1177/0954008308090277     Document Type: Article

References (37)

1. Pater, R.H. (1994). Thermosetting Polyimides: A Review, SAMPE J., 30: 29-38.
2. Meador, M.A. (1998). Recent Advances in the Development of Processable High-temperature Polymers, Ann. Rev. Mater. Res., 28: 599-630.
3. Connell, J.W., Smith Jr, J.G. and Hergenrother, P.M. (2000). Oligomers and Polymers containing Phenylethynyl Groups, J. Macromol. Sci.-Rev. Macromol. Chem. Phys., 40: 207-230.
4. Hergenroth, P.M. (2003). The Use, Design, Synthesis, and Properties of High Performance/High Temperature Polymers: An Overview, High Perform. Polym., 15: 3-45.
5. Serafini, T.T., Delvigs, P. and Lightsey, G.R. (1972). Thermally Stable Polyimides from Solutions of Monomeric Reactants, J. Appl. Polym. Sci., 16: 905-915
6. Chuang, K.C., Bowles, K.J., Papadopoulos, D.S., Hardy-Green, D. and McCorkle, L.S. (2001). A High Tg PMR Polyimide Composites (DMBZ-15), J. Adv. Mater., 33: 33-38.
7. Chuang, K.C., Bowman, C.L., Tsotsis, T.K. and Arendt, C.P. (2003). 6F-polyimides with Phenylethynyl Endcap for 315-370°C Applications, High Perform. Polym., 15: 459-472.
8. Simone, C.D., Xiao, Y.M., Sun. X.D. and Scola. D.A. (2005). Some Aspects of the Cure of RP-46, a Nadic End-capped Polyimide, and Phenyl Nadimide and Bis-nadic-3,4 Prime -ODA Model Compounds, High Perform. Polym., 17: 51-72.
9. Grenier-Loustalot, M.F. and Billon, L. (1996). New Thermostable Systems: Structure/property Relationships of Nadic Terminated Telechelic Fluorine Polyimides, Polym. Int., 41: 135-149.
10. Jensen, B.J., Hergenrother, P.M. and Nwokogu, G. (1993). Polyimides with Pendent Ethynyl Groups, Polymer., 34: 630-635.
11. Chen, J.S., Yang, S.Y., Tao, Z.Q., Hu, A.J., Gao, S.Q. and Fan, L. (2006). Short Carbon Fiber-reinforced PMR Polyimide Composites with Improved Thermo-oxidative and Hygrothermal Stabilities, High Perform. Polym., 18: 265-282.
12. Chen, J.S., Yang, S.Y., Tao, Z.Q., Hu, A.J. and Fan, L. (2006). Processing and Properties of Carbon Fiber-reinforced PMR Type Polyimide Composites, High Perform. Polym., 18: 377-396.
13. Bryant, R.G., Jensen, B.J. and Hergenrother, P.M. (1996). Chemistry and Properties of a Phenylethynyl-terminated Polyimide, J. Appl. Polym. Sci., 59: 1249-1254.
14. Hinkley, J.A. and Jensen, B.J. (1996). Crosslinking in Phenylethynyl-terminated Polyimides, High Perform. Polym., 8: 599-605.
15. Fang, X.M., Xie, X.Q., Simone, C.D., Stevens, M.P. and Scola, D.A. (2000). Solid-state 13C NMR Study of the Cure of 13C-labeled Phenylethynyl End-capped Polyimides, Macromolecules, 33: 1671-1681.
16. Simone, C.D. and Scola, D.A. (2003). Phenylethynyl End-capped Polyimides Derived from 4,4 prime -(2,2,2-trifluoro-1-phenylethylidene)diphthalic anydride, 4,4 prime (hexafluoro -isopropylidene)diphthalic anhydride, and 3,3 prime, 4,4 prime -biphenylene dianhydride: Structure-viscosity Relationship, Macromolecules, 36: 6780-6790.
17. Li, Y.T., Murphy, L.A., Lincoln, J.E. and Morgan, R.J. (2007). Phenylethynyl End-capped Fluorinated Imide Oligomer AFR-PEPA-N: Morphology and Processibility Characteristics, Macromol. Mater. Eng., 292: 78-84.
18. Hou, T.H. (2006). Processing Robustness for a Phenylethynyl-terminated Polyimide Composite, J. Appl. Polym. Sci., 100: 3212-3221.
19. Sasaki, T. and Yokota, R. (2006). Synthesis and Properties of an Addition-type Imide Oligomer having Pendent Phenylethynyl Groups: Investigation of Curing Behavior, High Perform. Polym., 18: 199-211.
20. Zhou, H.W., Chen, C.H., Kanbara, R., Sasaki, T. and Yokota, R. (2005). Isomeric Dianhydrides based Modified Phenylethynyl-terminated Addition-type Imide Oligomers. High Perform. Polym., 17: 193-212.
21. Hergenrother, P.M., Connell, J.W. and Smith Jr, J.G. (2000). Phenylethynyl containing Imide Oligomers. Polymer, 41: 5073-5081.
22. Connell, J.W., Smith Jr, J.G. and Hergenrother, P.M. (1997). Properties of Imide Oligomers containing Pendent Phenylethynyl Groups, High Perform. Polym., 9: 309-321.
23. Johnston, J.A., Li, F.M., Harris, F.W. and Takekoshi, T. (1994). Synthesis and Characterization of Imide Oligomers End-capped with 4-(phenylethynyl)phthalic anhydrides, Polymer, 35: 4865-4765.
24. Hou, T.H., Belvin, H.L. and Johnston, N.J. (2001). Automated Tow Placed LaRC-PETI-5 Composites, High Perform. Polym., 13: 323-336.
25. Smith Jr, J.G., Connell, J.W. and Hergenrother. P.M. (2000). Effect of Phenylethynyl Terminated Imide Oligomer Molecular Weight on the Properties of Composites, J. Compos Mater., 34: 614-628.
26. Hou, T.H., Jensen, B.J. and Hergenrother, P.M. (1996). Processing and Properties of IM7/PETI Composites, J. Compos Mater., 30: 109-122.
27. Connell, J.W., Smith Jr, J.G., Hergenrother. P.M. and Criss, J.M. (2003). High Temperature Transfer Molding Resins: Laminate Properties of PETI-298 and PETI-330, High Perform. Polym., 15: 375-394.
28. Smith Jr, J.G., Connell, J.W., Hergenrother. P.M., Ford, L.A. and Criss Jr, J.M. (2003). Transfer Molding Imide Resins Based on 2,3,3 prime, 4 prime -Biphenyltetracarboxylic Dianhydride, Macromol. Symp., 199: 401-418.
29. Connell, J.W., Smith Jr, J.G., Hergenrother, P.M. and Criss Jr, J.G. (2004). High Temperature Transfer Molding resins: Preliminary Composite Properties of PETI-375, International SAMPE Symposium and Exhibition (Proceedings), 49:1615-1626.
30. Rao, X.H., Zhou, H.W., Dang, G.D., Chen, C.H. and Wu, Z.W. (2006). New Kinds of Phenylethynyl-terminated Polyimide oligomers with Low Viscosity and Good Hydrolytic Stability, Polymer, 47: 6091-6098.
31. Ding, M.X. (2007). Isomeric Polyimides, Prog. Polym. Sci., 32: 623-668.
32. Hergenrother, P.M., Watson, K.A., Smith Jr, J.G., Connell, J.W. and Yokota, R. (2002). Polyimides from 2,3,3 prime, 4 prime -biphenyltetracarboxylic dianhydride and aromatic diamines, Polymer, 43: 5077-5093.
33. Yang, S.Y., Ge, Z.Y., Yin, D.X., Liu, J.G., Li, Y.F. and Fan, L. (2004). Synthesis and Characterization of Novel Fluorinated Polyimides Derived from 4,4 prime -[2,2,2-trifluoro-1-(3-trifluoromethylphenyl)ethylidene]diphthalic Anhydride and Aromatic Diamines, J. Polym. Sci. Pol. Chem., 42: 4143-4152.
34. Xie, K., Zhang, S.Y., Liu, J.G., He, M.H. and Yang, S.Y. (2001). Synthesis and Characterization of Soluble fluorine-containing Polyimides Based on 1,4-bis(4-amino-2-trifluoromethylphenoxy) Benzene, J. Polym. Sci. Pol. Chem., 39: 2581-2590.
35. Chen, J.S., Zuo, H.J., Yang, H.X., Liu, J.G., Fan, L. and Yang, S.Y. (2006). Synthesis and characterization of high temperature transfer molding polyimide resins, J. Aeronaut. Mater., 26: 183-186.
36. Hergenrother, P.M. and Smith, J.G. (1994). Chemistry and Properties of Imide Oligomers End-capped with Phenylethynylphthalic Anhydrides, Polymer, 35: 4857-4864.
37. Fang, X.M., Rogers, D.F. and Scola, D.A. (1998). Study of the Thermal Cure of a Phenylethynyl-terminated Imide Model Compound and a Phenylethynyl-terminated Imide Oligomer (PETI-5), J. Polym. Sci. Pol. Chem., 36: 461-470.