Synthesis and properties of transparent polyimides derived from 1,4-cyclohexylene bis(trimellitate anhydride)

Abstract

A series of polyimides (PIs) derived from 1,4-cyclohexylene bis(trimellitate anhydride) (TACH) was synthesized by conventional two-step method with chemical imidization. The resulting PIs had glass transition temperatures (T_g s) in the range of 188–240°C and exhibited good mechanical properties with tensile strengths of 50.0–90.2 MPa, tensile moduli of 2.2–3.9 GPa, and elongations at break of 2.9–5.8%. These PI films showed high optical transparency with cut-off wavelengths of 345–369 nm and high transmittance at 500 nm with more than 84%. Compared with PIs derived from 1,4-bis(3,4-dicarboxyphenoxy)cyclohexane dianhydride, the TACH-based PIs showed higher T_g , better solubility, and competitive transparency.

Keywords

Transparent polyimides bis(ester anhydride)cyclohexane

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References

Ghosh

Mittal

. Polyimides: fundamentals and applications. New York: Marcel Dekker, 1996.

Feger

Khojasteh

Molis

. Polyimides: trends in materials and applications. New York: Society of Plastic Engineers, 1996.

Mittal

. Polyimides and other high temperature polymers: synthesis, characterization and application. The Netherlands: VSP, 2001.

Ando

Ueda

Kakimoto

. The latest polyimides: fundamentals and applications. 2nd ed. Tokyo: NTS, 2010.

Liaw

Wang

Huang

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

Hasegawa

Horie

. Photophysics, photochemistry, and optical properties of polyimides. Prog Polym Sci 2001; 26: 259–335.

Ando

Matsuura

Sasaki

. Coloration of aromatic polyimides and electronic properties of their source materials. Polym J 1997; 29: 69–76.

Masatoshi

Tomohiro

Junichi

. Solution-processable transparent polyimides with low coefficients of thermal expansion and self-orientation behavior induced by solution casting. Eur Polym J 2013; 49: 3657–3672.

Chen

Yang

Hsiao

. Novel organosoluble and colorless poly(ether imide)s based on 1,1-bis[4-(3,4-dicarboxyphenoxy)phenyl]cyclohexane dianhydride and trifluoromethyl-substituted aromatic bis(ether amine)s. Eur Polym J 2006; 42: 1705–1715.

10.

Yang

Hsu

. Organo-soluble and lightly-colored fluorinated polyimides based on 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]hexafluoropropane dianhydride and aromatic bis(ether amine)s bearing pendent trifluoromethyl groups. Polym J 2006; 38: 132–144.

11.

Yang

. Colorless polyimides from 2,3,3′,4′-biphenyltetracarboxylic dianhydride (a-BPDA) and various aromatic bis(ether amine)s bearing pendent trifluoromethyl groups. Polymer 2005; 46: 5797–5807.

12.

Yang

Wen

. Highly optically transparent/low color polyimide films prepared from hydroquinone- or resorcinol-based bis(ether anhydride) and trifluoromethyl-containing bis(ether amine)s. Polymer 2006; 47: 7021–7033.

13.

Yang

Wang

. Thermally stable, organosoluble, and colorless poly(ether imide)s having ortho-linked aromatic units in the main chain and trifluoromethyl pendent groups. Macromol Chem Phys 2006; 207: 1049–1061.

14.

Yang

Hsiao

. Highly soluble and optically transparent poly(ether imide)s based on 2,6- or 2,7-bis(3,4-dicarboxyphenoxy)naphthalene dianhydride and aromatic bis(ether amine)s bearing trifluoromethyl groups. J Polym Sci Part A: Polym Chem 2006; 44: 5909–5922.

15.

Watson

Palmieri

Connell

. Space environmentally stable polyimides and copolyimides derived from [2,4-bis(3-aminophenoxy)phenyl]diphenylphosphine oxide. Macromolecules 2002; 35: 4968–4974.

16.

Clair AK

Clair TL

. Process for preparing highly optically transparent/colorless aromatic polyimide film. Patent 4603061, USA, 1986.

17.

Matsuura

Ando

Sasaki

. Polyimides derived from 2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl. 4. Optical properties of fluorinated polyimides for optoelectronic components. Macromolecules 1994; 27: 6665–6670.

18.

Yang

Hsiao

. Organosoluble and light-colored fluorinated polyimides derived from 2,3-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic dianhydrides. Polymer 2003; 44: 7067–7078.

19.

Yang

Chen

Hsiao

. Optically transparent and colorless poly(ether-imide)s derived from a phenylhydroquinone bis(ether anhydride) and various trifluoromethyl-substituted bis(ether amine)s. J Polym Res 2010; 17: 779–788.

20.

Fan

Yang

. Synthesis and characterization of novel fluorinated polyimides derived from 1,1′-bis(4-aminophenyl)-1-(3-trifluoromethylphenyl)-2,2,2-trifluoroethane and aromatic dianhydrides. Eur Polym J 2008; 44: 1252–1260.

21.

Liu

Zhang

Guan

. Synthesis and properties of soluble fluorinated poly(ether imide)s with different pendant groups. Polymer 2008; 49: 5439–5445.

22.

Liu

Gao

. Organo-soluble and transparent polyimides containing phenylphosphine oxide and trifluoromethyl moiety: synthesis and characterization. Eur Polym J 2009; 45: 1139–1148.

23.

Yang

. Colorless and high organosoluble polyimides from 2,5-bis(3,4-dicarboxyphenoxy)-t-butylbenzene dianhydride and aromatic bis(ether amine)s bearing pendent trifluoromethyl groups. Polymer 2005; 46: 5778–5788.

24.

Yang

. Novel organosoluble and colorless poly(ether imide)s based on 3,3-bis[4-(3,4-dicarboxyphenoxy)phenyl] phthalide dianhydride and aromatic bis(ether amine)s bearing pendent trifluoromethyl groups. J Polym Sci Part A: Polym Chem 2006; 44: 3140–3152.

25.

Yamada

Kusama

Matsumoto

. Soluble polyimides with polyalicyclic structure. 2. Polyimides from bicyclo[2.2.1]heptane-2-exo-3-exo-5-exo-6-exo-tetracarboxylic 2,3:5,6-dianhydride. Macromolecules 1993; 26: 4961–4963.

26.

Matsumoto

Kurosaki

. Soluble polyimides with polyalicyclic structure. 4. Colorless polyimides from bicyclo[2.2.1] heptane-2-endo,3-endo,5-exo,6-exo-tetracarboxylic 2,3:5,6-dianhydride. Macromolecules 1995; 28: 5684–5685.

27.

Matsumoto

Kurosaki

. Soluble and colorless polyimides from bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic 2,3:5,6-dianhydrides. Macromolecules 1997; 30: 993–1000.

28.

Shiotani

Shimazaki

Matsuo

. Preparation of transparent polyimides derived from cis- and trans-dicyclohexyl-3,3′,4,4′-tetracarboxylic dianhydrides. Macromol Mater Eng 2001; 286: 434–441.

29.

Matsumoto

. Nonaromatic polyimides derived from cycloaliphatic monomers. Macromolecules 1999; 32: 4933–4939.

30.

Liu

Zhou

. Organosoluble and transparent polyimides derived from alicyclic dianhydride and aromatic diamines. J Polym Sci Part A: Polym Chem 2002; 40: 110–119.

31.

Mathews

Kim

. Synthesis and characterization of novel fully aliphatic polyimidosiloxanes based on alicyclic or adamantyl diamines. J Polym Sci Part A: Polym Chem 2006; 44: 5254–5270.

32.

Yamashita

Ogawa

Koshikawa

. Synthesis and optical properties of EB induced refractive index lithography materials based on aliphatic polyimides. J Photopolym Sci Technol 2007; 20: 739–742.

33.

Hasegawa

Kasamatsu

Koseki

. Colorless poly(ester imide)s derived from hydrogenated trimellitic anhydride. Eur Polym J 2012; 48: 483–498.

34.

Zhai

Yang

Fan

. Preparation and characterization of highly transparent and colorless semi-aromatic polyimide films derived from alicyclic dianhydride and aromatic diamines. Polymer 2012; 53: 3529–3539.

35.

Hasegawa

Hirano

Fujii

. Solution-processable colorless polyimides derived from hydrogenated pyromellitic dianhydride with controlled steric structure. J Polym Sci Part A: Polym Chem 2013; 51: 575–592.

36.

Fang

Yang

Zhang

. Synthesis and properties of polyimides derived from cis- and trans-1,2,3,4-cyclohexanetetracarboxylic dianhydrides. Polymer 2004; 45: 2539–2549.

37.

Chen

Pei

Liu

. Synthesis and properties of transparent polyimides derived from trans- and cis-1,4-bis(3,4-dicarboxyphenoxy)cyclohexane dianhydrides. J Polym Res 2013; 20: 159.

38.

Zhao

Chen

Zhou

. Synthesis and characterization of organosoluble and transparent polyimides derived from trans-1,2-bis(3,4-dicarboxyphenoxy)cyclohexane dianhydride. J Appl Polym Sci 2015; 132: 4 2317.

39.

Zhou

Chen

Zhao

. Synthesis and properties of transparent polyimides derived from trans-1,4-bis(2,3-dicarboxyphenoxy)cyclohexane dianhydride. RSC Adv 2015; 5: 53926–53934.

40.

Lienert

. Poly(ester-imide)s for industrial use. Adv Polym Sci 1999; 141: 45–82.

41.

Hasegawa

Tominaga

. Fluorene-containing poly(ester imide)s and their application to positive-type photosensitive heat-resistant materials. Macromol Mater Engng 2011; 296: 1002–1017.

42.

Hasegawa

Sakamoto

Tanaka

. Poly(ester imide)s possessing low coefficients of thermal expansion (CTE) and low water absorption (III). Use of bis(4-aminophenyl)terephthalate and effect of substituents. Eur Polym J 2010; 46: 1510–1524.

43.

Hasegawa

Koseki

. Poly(ester imide)s possessing low coefficient of thermal expansion and low water absorption. High Perform Polym 2006; 18: 697–717.

44.

Jeng

Pei

Chun

. Synthesis and characterization of novel polyesterimides. J Appl Polym Sci 2004; 94: 730–738.

45.

Hasegawa

Tsujimura

Koseki

. Poly(ester imide)s possessing low CTE and low water absorption (II). Effect of substituents. Polym J 2008; 40: 56–67.

46.

Zhou

Chen

Wang

. Comparative study of transparent polyimides derived from bis(ether anhydride)s and bis(ester anhydride)s using 2,2′-bis(trifluoromethyl)biphenyl-4,4′-diamine. High Perform Polym 2017; 29: 218–226.

47.

Satoh

Morikawa

. Synthesis and characterization of aromatic polyimides containing trifluoromethyl group from bis(4-amino-2-trifluoromethylphenyl)ether and aromatic tetracarboxylic dianhydrides. High Perform Polym 2010; 22: 412–427.

48.

Yang

. Organosoluble and light-colored fluorinated polyimides from 2,2-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]sulfone and aromatic dianhydrides. J Polym Res 2005; 12: 257–269.

49.

Zhou

Chen

Wang

. Synthesis and characterization of transparent polyimides derived from ester-containing dianhydrides with different electron affinities. RSC Adv 2015; 5: 79207–79215.