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Modified biphenyl type dianhydride intermediate containing cyano side chain and synthesis method and application thereof

A technology of biphenyl tetraacid dianhydride and biphenyl type, which is applied in the field of cyano side chain modified biphenyl type dianhydride intermediates and its synthesis, which can solve poor solubility, difficult material processing, high melting temperature, etc. question

Active Publication Date: 2012-01-25
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this kind of polyimide is difficult to process due to its poor solubility and high melting temperature [C.E.Srong, Prog.Polym.Sci., 1991; 16:561]

Method used

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  • Modified biphenyl type dianhydride intermediate containing cyano side chain and synthesis method and application thereof
  • Modified biphenyl type dianhydride intermediate containing cyano side chain and synthesis method and application thereof
  • Modified biphenyl type dianhydride intermediate containing cyano side chain and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Embodiment 1: 2,2'-dicyano-4,4',5,5'-biphenyltetraacid dianhydride preparation (former example 2)

[0077] The processing steps of the present embodiment are as follows:

[0078] (1) raw material is 20.00g biphenyltetraic dianhydride and 440mL composite solvent, described composite solvent is formulated by 400mL methanol and 40mL vitriol oil; Add biphenyltetrapic dianhydride in the flask, then add described composite solvent , and then heated to 85°C under normal pressure to reflux for 16 hours. After the reflux time expired, stand still for 12 hours and filter. The obtained filter cake was washed with methanol and distilled water to remove sulfuric acid, and dried in an oven at 70°C for 12 hours to obtain White tetramethyl biphenyl tetracarboxylate 23.36g, yield 88.97%; 1 HNMR (400MHz, CDCl 3 -d 6 ): δ8.73 (s, 2H), 8.22 (d, 2H), 7.96 (d, 2H), 3.88 (s, 12H).

[0079] (2) raw material is 15.00g tetramethyl biphenyl tetracarboxylate, sulfuric acid and 16.22g sodium br...

Embodiment 2

[0084] Example 2: Preparation of 2-dicyano-2'-phenoxy-4,4',5,5'-biphenyltetraacid dianhydride

[0085] The processing steps of the present embodiment are as follows:

[0086] (1) raw material is 25.00g biphenyltetraic dianhydride and 394mL composite solvent, described composite solvent is formulated by 375mL methyl alcohol and 19mL vitriol oil; Add biphenyltetraic dianhydride in the flask, then add described composite solvent , and then heated to 80°C under normal pressure to reflux for 10 hours. After the reflux time expired, stand still for 10 hours and filter. The obtained filter cake was washed with methanol and distilled water to remove sulfuric acid, and dried in an oven at 70°C for 12 hours to obtain a white The yield of tetramethyl biphenyl tetracarboxylate is 87.44%; 1 HNMR (400MHz, CDCl 3 -d 6 ): δ8.73 (s, 2H), 8.22 (d, 2H), 7.96 (d, 2H), 3.88 (s, 12H).

[0087] (2) raw material is 15.00g tetramethyl biphenyl tetracarboxylate, sulfuric acid and 13.90g potassium b...

Embodiment 3

[0093] Example 3: Preparation of 2-dicyano-2'-p-tert-butylphenoxy-4,4',5,5'-biphenyltetraacid dianhydride

[0094] The processing steps of the present embodiment are as follows:

[0095] (1) raw material is 20.00g biphenyl tetraacid dianhydride and 575mL composite solvent, described composite solvent is formulated by 500mL methanol and 75mL vitriol oil; Add biphenyl tetraacid dianhydride in the flask, then add described composite solvent , and then heated to 95°C under normal pressure to reflux for 24 hours. After the reflux time expired, stand still for 12 hours and filter. The obtained filter cake was washed with methanol and distilled water to remove sulfuric acid, and dried in an oven at 70°C for 12 hours to obtain a white Tetramethyl biphenyl tetracarboxylate, yield 82.88%; 1 HNMR (400MHz, CDCl 3 -d 6 ): δ8.73 (s, 2H), 8.22 (d, 2H), 7.96 (d, 2H), 3.88 (s, 12H).

[0096] (2) raw material is 15.00g tetramethyl biphenyl tetracarboxylate, sulfuric acid and 14.28g potassiu...

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Abstract

The invention relates to a modified biphenyl type dianhydride intermediate containing a cyano side chain, and the structural formula is as follows, in the structural formula, R is -O-R1 or -S-R1 or -CN. The intermediate can be prepared by two preparation methods, and the first preparation method comprises the following steps: (1) the preparation of a second compound; (2) the preparation of a third compound; (3) the preparation of a fourth compound; (4) the preparation of a fifth compound; and (5) the preparation of the modified biphenyl type dianhydride intermediate containing the cyano side chain. The second preparation method comprises the following steps: (1) the preparation of the second compound; (2) the preparation of the third compound; (3) the preparation of the fourth compound-a; (4) the preparation of the fourth compound-b; (5) the preparation of the fifth compound; and (6) the preparation of the modified biphenyl type dianhydride intermediate containing the cyano side chain.

Description

technical field [0001] The invention belongs to the field of polymer materials, and in particular relates to a modified biphenyl dianhydride intermediate containing a cyano group side chain and a synthesis method and application thereof. Background technique [0002] Polyimide refers to a class of polymers containing imide rings in the main chain structure. Such polymers have been reported as early as 1908. Nowadays, polyimide has attracted much attention because of its outstanding comprehensive properties and wide application fields. Current research focuses on aromatic polyimides, because such polyimides have excellent thermal stability, mechanical properties, chemical inertness, dielectric properties and radiation resistance, for example, by 3,3′,4 , 4'-biphenyldianhydride and polyimide formed by polycondensation of p-phenylenediamine, its thermal decomposition temperature is as high as 600 ℃. However, this kind of polyimide is difficult to process due to its poor solub...

Claims

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Application Information

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IPC IPC(8): C07D307/89C08G73/12
Inventor 杨刚朱俊高帅曾科赵永超胡军申晓华
Owner SICHUAN UNIV
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