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Dianhydrides, polyimides, methods of making each, and methods of use

A technology of polyimide and bromosuccinimide, which is applied to dianhydride and polyimide, and can solve problems such as poor processability

Active Publication Date: 2016-02-10
KING ABDULLAH UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most polyimides exhibit poor processability due to their high melting point and limited solubility in organic solvents
Microporous polyimides have been developed to overcome these deficiencies, however, microporous polyimides are challenging to synthesize (at least in part) due to limitations in suitable reagents

Method used

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  • Dianhydrides, polyimides, methods of making each, and methods of use
  • Dianhydrides, polyimides, methods of making each, and methods of use
  • Dianhydrides, polyimides, methods of making each, and methods of use

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[0084] Now that embodiments of the present invention have been generally described, examples describe some other embodiments. Although embodiments of the invention have been described in conjunction with examples and corresponding text and drawings, it is not intended to limit embodiments of the invention to these descriptions. On the contrary, the intention is to cover all alternatives, modifications and equivalents included within the spirit and scope of embodiments of the invention.

example 1

[0087] Synthesis of 2,2',3,3'-tetracarboxy-9,9'-spirobifluorene

[0088] 2,2',3,3'-Tetracyano-9,9'-spirobifluorene (624 mg, 1.50 mmol) was mixed with a water / ethanol (10 mL / 10 mL) solution. Next, KOH (1740 mg, 30 mmol) was added slowly, and the mixture was refluxed overnight. After cooling the solution to room temperature, it was poured into acid (HCl, 6N) to adjust the pH to 1-2. After removal of ethanol and water, methanol was added again to dissolve the product and filtered to remove the organic phase. After this time, THF (20 mL) was added to the solid, filtered, and the THF solution was added dropwise to 300 mL of DCM. After filtration, an off-white solid was obtained.

example 2

[0090] Synthesis of 2,2',3,3'-dianhydride-9,9'-spirobifluorene

[0091] 2,2',3,3'-Tetracarboxy-9,9'-spirobifluorene (1.06 g, 2.15 mmol) was added to Ac 2 in 0 (15 mL). The solution was refluxed for 6 hours and filtered to obtain needle crystals: 0.9 g (yield: 98%). 1 HNMR (400MHz, CDCl 3 ): 8.45(s, 2H), 8.07(d, 2H, J=7.72Hz), 7.58(t, 2H, J=7.48Hz, 7.50Hz), 7.36(t, 2H, J=7.48Hz, 7.50Hz) , 7.24(s, 2H), 6.82(d, 2H, J=7.68Hz). Analysis: C 29 H 12 O 6 Calculated: C, 76.32; H, 2.65; found: C, 75.42; H, 2.06; HRMS: C 25 H 18 N 2 O 2 Calculated: 456.0634; Experimental: 406.06284.

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Abstract

Embodiments of the present disclosure provide for an aromatic dianhydride, a method of making an aromatic dianhydride, an aromatic dianhydride-based polyimide, a method of making an aromatic dianhydride-based polyimide, and the like.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS [0002] This application claims US Provisional Application Serial No. 61 / 842,104, entitled "Dianhydrides, Polyimides, Methods of Making and Using (DIANHYDRIDES, POLYIMIDES, METHODSOFMAKINGEACH, ANDMETHODSOFUSE)", filed on July 2, 2013 , which is incorporated herein by reference in its entirety. Background technique [0003] Polyimide is one of the most important high performance glassy polymers exhibiting superior thermal, chemical and mechanical properties. Polyimides have been used in many fields, including the aerospace industry, the electronics industry, high temperature adhesion, membranes for separation, composite materials, and the like. However, most polyimides exhibit poor processability due to their higher melting points and limited solubility in organic solvents. Microporous polyimides have been developed to overcome these deficiencies, however, microporous polyimides are challenging to synthesize (at least in part)...

Claims

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Application Information

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IPC IPC(8): C07D493/04C07D493/08C07D493/10C07D307/89C07D307/92C07D487/10C07D209/48C07D209/66C08G73/10
CPCC07D487/10C07D209/48C07D209/66C07D307/89C07D307/92C08G73/10C07D493/10C08G73/1085C08G73/1071B01D71/64C08G73/1007C08G73/1067
Inventor 马小华恩果·品瑙贝德·葛哈奈姆
Owner KING ABDULLAH UNIV OF SCI & TECH