Novel copolyimides containing 1,4:3,6-dianhydro- d -mannitol unit Preparation,characterization,thermal,mechanical,soluble,and optical properties

Abstract

In order to obtain colorless and soluble polyimide films, a dianhydride containing 1,4:3,6-dianhydro-d-mannitol unit, 2,5-bis(3,4-dicarboxyphenoxy)-1,4:3,6-dianhydromannitol dianhydride (IMDA) was synthesized. And a series of copolyimides were prepared from IMDA, 1,2,4,5-benzenetetracarboxylic anhydride (PMDA), and 4,4′-oxydianiline by adjusting the mole fraction (between IMDA and PMDA) of IMDA from 0% to 100%. It was found that the solubility as well as the transmittance of the copolyimide films enhanced with the increased content of IMDA. Especially, when the content of IMDA was 60% or more, the copolyimides were readily soluble in common polar solvents and could afford flexible, tough, and colorless films with transparency up to 84% at 450 nm, which may be ascribed to the incorporation of the relatively twisted and flexible 1,4:3,6-dianhydro-d-mannitol units into the backbone of copolyimides. Additionally, the influence of IMDA on the thermal, mechanical, and morphological properties of copolyimides was investigated.

Keywords

Dianhydride copolyimide

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References

Spechler

Koh

Herb

. A transparent, smooth, thermally robust, conductive polyimide for flexible electronics. Adv Funct Mater 2015; 25: 7428–7434.

Erhard

Richter

Bartz

CBA

. Fluorinated aromatic polyimides as high-performance electret materials. Macromol Rapid Commun 2015; 36: 520–527.

Nam

Kim

Choi

. Thermomechanical and optical properties of molecularly controlled polyimides derived from ester derivatives. Polymer 2017; 108: 502–512.

Yeo

Goh

. Synthesis and characterization of highly-fluorinated colorless polyimides derived from 4,4′-((perfluoro-[1,1′-biphenyl]-4,4′-diyl)bis(oxy))bis(2,6-dimethylaniline) and aromatic dianhydrides. Polymer 2015; 76: 280–286.

Kim

Chung

. Soluble and transparent polyimides from unsymmetrical diamine containing two trifluoromethyl groups. J Polym Sci Part A: Polym Chem 2013; 51: 4413–4422.

Liu

Wang

. A review on colorless and optically transparent polyimide films: chemistry, process and engineering applications. J Ind Eng Chem 2015; 28: 16–27.

Fenouillot

Rousseau

Colomines

. Polymers from renewable 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide): A review. Prog Polym Sci 2010; 35: 578–622.

Jasinska

Villani

. Novel, fully biobased semicrystalline polyamides. Macromolecules 2011; 44: 3458–3466.

Noordover

BAJ

van Staalduinen

Duchateau

. Co- and terpolyesters based on isosorbide and succinic acid for coating applications: synthesis and characterization. Biomacromolecules 2006;7: 3406–3416.

10.

Marín

Alla

Martínez de Ilarduya

. Carbohydrate-based polyurethanes: a comparative study of polymers made from isosorbide and 1,4-butanediol. J Appl Polym Sci 2012; 123: 986–994.

11.

Juais

Naves

. Isosorbide polyesters from enzymatic catalysis. Macromolecules 2010; 43: 10315–10319.

12.

Śmiga-Matuszowicz

Janicki

Jaszcz

. Novel bioactive polyester scaffolds prepared from unsaturated resins based on isosorbide and succinic acid. Mat Sci Eng C 2014; 45: 64–71.

13.

Yan

Liu

. Synthesis and properties of polyimides derived from bis(4-aminophenyl)isohexides. High Perform Polym 2017; 29: 197–204.

14.

Liu

Tian

. Soluble polyimides containing 1,4:3,6-dianhydro-d-glucidol and fluorinated units: preparation, characterization, optical, and dielectric properties. J Polym Sci Part A: Polym Chem 2017; 55: 3253–3265.

15.

Wang

Yan

. Partially bio-based polyimides from isohexide-derived diamines. Polymer 2015; 74: 38–45.

16.

Williams

Donahue

. Reactions of phenoxides with nitro- and halo-substituted phthalimides. J Org Chem 1977; 42: 3414–3419.

17.

Ghanem

Salines

. Synthesis and effect of physical aging on gas transport properties of a microporous polyimide derived from a novel spirobifluorene-based dianhydride. ACS Macro Lett 2015; 4: 231–235.

18.

Yang

Zhang

Huang

. Synthesis of novel biobased polyimides derived from isomannide with good optical transparency, solubility and thermal stability. RSC Adv 2015; 5: 67574–67582.

19.

Erman

Flory

Hummel

. Moments of the end-to-end vectors for p-phenylene polyamides and polyesters. Macromolecules 1980; 13: 484–491.

20.

Guan

Wang

. High transparent polyimides containing pyridine and biphenyl units: synthesis, thermal, mechanical, crystal and optical properties. Polymer 2015; 62: 1–10.

21.

Kim

Lee

Heo

. Soluble polyimides with trifluoromethyl pendent groups. Polymer 2013; 54: 5648–5654.

22.

Liu

Chen

. Preparation of hydrophilic and antifouling polysulfone ultrafiltration membrane derived from phenolphthalin by copolymerization method. Appl Surf Sci 2017; 401: 69–78.

23.

Tapaswi

Choi

Jung

. Synthesis and characterization of fully aliphatic polyimides from an aliphatic dianhydride with piperazine spacer for enhanced solubility, transparency, and low dielectric constant. J Polym Sci Part A: Polym Chem 2014; 52: 2316–2328.

24.

Chern

. Novel 1,6-bis[4-(4-aminophenoxy)phenyl]diamantane. Macromolecules 1998; 31: 5837–5844.

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