Synthesis and Properties of Polyimides Containing Phthalide Groups

Yun-hua Lu; Wei Wang; Guo-yong Xiao; Hong-bin Zhao; Yan Dong; Chi Hai-jun; Tong-hua Wang; Zhi-zhi Hu

doi:10.11777/j.issn1000-3304.2016.15348

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Synthesis and Properties of Polyimides Containing Phthalide Groups

Research Bulletin | 更新时间：2021-03-19

- Synthesis and Properties of Polyimides Containing Phthalide Groups
- Acta Polymerica Sinica Issue 6, Pages: 831-836(2016)
- 作者机构：
  
  1.辽宁科技大学化学工程学院鞍山 114051
  2.大连理工大学化工学院大连 116012
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2016.15348
  CLC：
- Published：2016-6，
  
  Received：16 December 2015，
  
  Revised：18 February 2016，
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Yun-hua Lu, Wei Wang, Guo-yong Xiao, Hong-bin Zhao, Yan Dong, Chi Hai-jun, Tong-hua Wang, Zhi-zhi Hu. Synthesis and Properties of Polyimides Containing Phthalide Groups. [J]. Acta Polymerica Sinica (6):831-836(2016)
DOI：

Yun-hua Lu, Wei Wang, Guo-yong Xiao, Hong-bin Zhao, Yan Dong, Chi Hai-jun, Tong-hua Wang, Zhi-zhi Hu. Synthesis and Properties of Polyimides Containing Phthalide Groups. [J]. Acta Polymerica Sinica (6):831-836(2016) DOI： 10.11777/j.issn1000-3304.2016.15348.

摘要

将酚酞分别和对氯硝基苯、2-氯-5-硝基三氟甲苯经Williamson反应得到3

3-双[(4-硝基苯氧基)苯基]酚酞和3

3-双[(4-硝基-2-三氟甲基苯氧基)苯基]酚酞;在Pd/C-水合肼还原作用下分别得到3

3-双[(4-氨基苯氧基)苯基]酚酞(Ⅰ)和3

3-双[(4-氨基-2-三氟甲基苯氧基)苯基]酚酞(Ⅱ).采用上述2种二胺单体分别与1

4-环丁烷四酸二酐(CBDA)、均苯四甲酸二酐(PMDA)、3

4-二苯醚四酸二酐(ODPA)和六氟二酐(6FDA)通过两步法制备出8种含酚酞基团的聚酰亚胺(PI)薄膜

然后采用核磁(NMR)、红外光谱(FTIR)、X-射线衍射仪(XRD)、紫外-可见分光光度计(UV-Vis)、热重分析仪(TGA)、示差扫描量热仪(DSC)和溶解性测试等测试手段和方法对所得到的PI的化学结构、光学性能、热性能和和溶解性等性质进行表征.研究结果表明

这些PI主要表现出非晶结构

且具有良好的溶解性和热性能;除PMDA基PI外

其余PI均表现出良好的浅色、透明特性.

Abstract

3-Bis[4-(4-aminophenoxy)phenyl]phthalide (Ⅰ) and 3

3-bis[4-(4-amino-2-trifluoro-methylphenoxy)phenyl]

phthalide (Ⅱ) were prepared through the nucleophilic substitution reaction of 4-nitrochlorobenzene and 2-chloro-5-nitrobenzotrifluoride with phenolphthalein in the presence of potassium carbonate to yield the intermediate dinitro compounds 3

3-bis[4-(4-nitrophenoxy) phenyl]phthalide and 3

3-bis[4-(4-nitro-2-trifluoromethylphenoxy) phenyl]

phthalide

followed by catalytic reduction with hydrazine and Pd/C. Eight kinds of phthalide-containing polyimide (PI) films were prepared from diamines Ⅰ and Ⅱ and four kinds of dianhydrides 1

4-cyclobutanetetracarboxylic dianhydride (CBDA)

pyromellitic dianhydride (PMDA)

4'-oxydiphthalic anhydride (ODPA) and 4

4'-hexafluoroisopropylidinedi(phtalic anhydride) (6FDA)

via

thermal imidization of poly(amic acid)s separately. The chemical structure and properties of these PIs were characterized by Fourier transform infrared spectroscopy (FTIR)

X-ray diffraction (XRD)

ultraviolet-visible spectrophotometry (UV-Vis)

differential scanning calorimetry (DSC)

thermogravimetric analysis (TGA) and solubility testing. These obtained experimental results showed that these PIs containing phthalide groups showed excellent thermal properties

optical properties and solubility. These PIs exhibited amorphous structure and showed good solubility in some aprotic polar organic solvents such as NMP

DMF

even soluble in weak polar solvent such as THF. They also exhibited excellent thermal properties

10% thermal decomposition temperature above 498.9℃ and the glass transition temperature (

) above 258℃. The UV-Vis transmittance spectra showed that the PIs derived from CBDA

ODPA

6FDA possessed optically colorless and transparent properties in the visible region.These obtained PIs containing phthalide groups could be expected to be used in the microelectronic and opto-electronic applications.

关键词

聚酰亚胺酚酞基团溶解性热性能光学性能

Keywords

PolyimidesPhthalide groupSolubilityThermal propertyOptical property

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Related Institution

College of Material Science and Engineering, Huaqiao University

State Key Laboratory of Fine Chemicals, Department of Polymer Science & Materials, Dalian University of Technology

College of Applied Chemistry and Engineering, University of Science and Technology of China

Changchun Institute of Applied Chemistry, Chinese Academy of Sciences

School of Chemical Engineering, National Key Laboratory of Fine Chemical Engineering, Liaoning High Performance Polymer Engineering Research Center,Liaoning Key Laboratory of Polymer Science and Engineering, Dalian University of Technology

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