Synthesis,characterization,and properties of thermoplastic polyimides derived from 4,4’-(hexafluoroisopropylidene)diphthalic anhydride in diethylene glycol dimethyl ether

Abstract

By regulating the order of monomer addition, four kinds of copolymer polyimides (PIs) were prepared using diethylene glycol dimethyl ether (DEGDE) and N,N-dimethylacetamide (DMAc) as the solvents. The molecular weights of polyamide acids (PAAs) ranged from 3.8 × 10⁵ to 9.2 × 10⁵. All of the films displayed high glass transition temperatures (T_gs) ranging from 313°C to 346°C. The polymer films show excellent thermal stabilities with 5% weight loss at temperatures of 505–524°C and char yields at 800°C were as high as 55% under nitrogen. The peel strengths of flexible copper (Cu) clads were in the range from 0.337 N cm⁻¹ to 0.598 N cm⁻¹. Compared to the molecular weight and peel strength of fresh PAA, those of PAAs prepared using DMAc significantly decreased after storage for 3 months at 0°C. However, when DEGDE was used as the solvent, the molecular weights of the PAAs and the thermal properties of the PIs were maintained after long storage time.

Keywords

Thermoplastic polyimide stability

Get full access to this article

View all access options for this article.

References

Hariharan

Bhuvana

Amutha

. Synthesis and characterization of novel polyimides containing anthracene moiety. High Perform Polym 2006; 18: 893.

Zhou

Liu

Zhang

. Novel acetylene-terminated polyisoimides with excellent processability and properties comparison with corresponding polyimides. J Appl Polym Sci 2011; 122: 3493–3503.

Liaw

Wang

Huang

. Advanced polyimide materials: syntheses, physical properties and applications. Prog Polym Sci 2012; 37: 907–974.

Zhao

Liu

. Synthesis and properties of thermoplastic polyimides with ether and ketone moieties. J Polym Sci A Polym Chem 2010; 48: 2878–2884.

hara

Banerjee

. Fluorinated high-performance polymers: poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups. Prog Polym Sci 2010; 35: 1022–1077.

Zhang

. Synthesis and properties of novel organosoluble polyimides derived from 1,4-bis[4-(3,4-dicarboxylphenoxy)]triptycene dianhydride and various aromatic diamines. Polymer 2007; 48: 6246–6253.

Chern

Tsai

. Low dielectric constant and high organosolubility of novel polyimide derived from unsymmetric 1,4-Bis(4-aminophenoxy)-2,6-di-tert-butylbenzene. Macromolecules 2008; 41: 9556–9564.

Koerner

Strong

Smith

. Polymer design for high temperature shape memory: low crosslink density polyimides. Polymer 2013; 54: 391–402.

Bai

WSW

. New poly(ethylene oxide) soft segment-containing sulfonated polyimide copolymers for high temperature proton-exchange membrane fuel cells. J Membr Sci 2008; 313: 75–85.

10.

Bose

Kuila

Nguyen

TXH

. Polymer membranes for high temperature proton exchange membrane fuel cell: recent advances and challenges. Prog Polym Sci 2011; 36: 813–843.

11.

Saeed

Zhan

. Effects of monomer structure and imidization degree on mechanical properties and viscoelastic behavior of thermoplastic polyimide films. Eur Polym J 2006; 42: 1844–1854.

12.

Mehdipour-Ataei

Heidari

. Synthesis and characterization of novel soluble and thermally stable polyamides based on pyridine monomer. Macromol Symp 2003; 193: 159–168.

13.

Yang

Chen

. Polyimides based on 2,5-bis(4-aminophenoxy)biphenyl. J Polym Sci A Polym Chem 2002; 40: 429–438.

14.

Haque

Upadhyaya

Roy

. The changes in flexural properties and microstructures of carbon fiber bismaleimide composite after exposure to a high temperature. Comp Struct 2014; 108: 57–64.

15.

Echigo

Iwaya

Tomioka

. A novel polymerization process of poly(4,4’-oxydiphenylenepyromellitamic acid). Macromolecules 1995; 28: 3000.

16.

Frache

Monticelli

Nocchetti

. Thermal properties of epoxy resin nanocomposites based on hydrotalcites. Polym Degrad Stab 2011; 96: 164–169.

17.

Canosa

Alfieri

Giudice

. High-solids, one-coat paints based on aliphatic epoxy resin-siloxanes for steel protection. Prog Org Coat 2014; 77: 1459–1464.

18.

Hasanain

Wang

. New one-step synthesis of polyimides in salicylic acid. Polymer 2008; 49: 831–835.

19.

Iqbal

Norder

Mendes

. All-aromatic liquid crystalline thermosets with high glass transition temperatures. J Polym Sci A Polym Chem 2009; 47: 1368–1380.

20.

DineHart

Wright

. Thermal stability of aromatic polyimides: factors affecting the oxidative stability of poly-N, N′-(4,4′-diphenyl ether) pyromellitimide. J Appl Polym Sci 1967; 11: 609–627.

21.

Glaris

Coulon

Dorget

. Fluorinated epoxy resin as a low adhesive mould for composite material. Compos B Eng 2014; 63: 94–100.

22.

LaDou

. Printed circuit board industry. Int J Hyg Environ Health 2006; 209: 211–219.

23.

Deng

Zhou

Fan

. Release of interfacial thermal stress and accompanying improvement of interfacial adhesion in carbon fiber reinforced epoxy resin composites: induced by diblock copolymers. Compos A Appl Sci Manuf 2012; 43: 990–996.