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Biphenyl compound with dissymmetrical structure, preparation method and application thereof

A compound and asymmetric technology, applied in the direction of organic chemistry, can solve the problems of many by-products, increasing the purity of inorganic sodium ions, complex reactions, etc.

Active Publication Date: 2008-09-24
成都金桨高新材料有限公司
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Problems solved by technology

Biphenyl compounds can also be generated by using palladium carbon to catalyze the reaction of monosodium or disodium salts of phthalic acid compounds. This type of reaction does not require a strict anhydrous and oxygen-free environment, but its reaction is relatively complicated, and the obtained by-products There are more products, which will also increase the economic cost in the product purification stage
[0011] In addition, the raw material used in the method for preparing biphenyl compounds with palladium / carbon as a catalyst is halogenated phthalic acid monosodium salt or disodium salt (Chemical Journal, 2005, 56 (9), 1805), which will undoubtedly Increasing the content of inorganic sodium ions affects the purity of the product

Method used

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  • Biphenyl compound with dissymmetrical structure, preparation method and application thereof
  • Biphenyl compound with dissymmetrical structure, preparation method and application thereof
  • Biphenyl compound with dissymmetrical structure, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Embodiment 1 contains the synthesis of the I-1 monomer of N-methyl structure

[0077] Add 1.52g (0.038mol) of sodium hydroxide and 4.5g (0.019mol) of N-methyl-4-bromophthalimide into a 100mL three-necked flask, then add 15mL of distilled water, and add 0.225g of palladium carbon , then the temperature was raised to 90° C., a solution of hydroxylamine sulfate (1.53 g, 15 ml of water) was added dropwise, and stirred for 10 hours. After the reaction, hot filtration was obtained to obtain the filtrate, and the pH value was adjusted to 1.5 with an acid solution, and a precipitate was precipitated, which was filtered and dried to obtain the intermediate 1 containing N-methyl structure. Add 2.0 g of intermediate 1 into a 100 mL three-necked flask, add 15 g of concentrated sulfuric acid, heat up to 40°C and stir until homogeneous, add dropwise 0.64 ml of fuming nitric acid, and stir for 6 hours. After the reaction, the reaction solution was poured into a beaker containing 100m...

Embodiment 2

[0086] Embodiment 2 contains the synthesis of the 1-2 monomer of N-methyl structure

[0087] In a 500mL three-necked flask, 23.38g (0.064mol) of I-1 monomer containing N-methyl structure, 250mL of N,N-dimethylformamide (DMF), 10.61g (0.0768mol) of anhydrous potassium carbonate were added successively. ), 5.74g (0.0832mol) of sodium nitrite, stopped after reacting at 130°C for 18 hours in a nitrogen atmosphere. Slowly pour the reaction solution into 1000 mL of hydrochloric acid aqueous solution to precipitate (pH=2-3), stir well, a large amount of yellow precipitate appears, filter the precipitate, and wash with water and air-dry. Recrystallize with distilled water to obtain I-2 monomer containing N-methyl structure.

[0088] I-2 monomer containing N-methyl structure (hydroxyl in 3 position) 1 H-NMR (DMSO-d 6 , ppm):

[0089] 3.14(s, 6H, CH 3 ), 7.37-7.39 (d, 1H, Ar-H), 7.89-7.92 (m, 2H, Ar-H), 8.18-8.20 (d, 1H, Ar-H), 8.34-8.36 (d, 1H, Ar-H) -H), 9.31(s, 1H, OH).

[009...

Embodiment 3

[0096] Embodiment 3 contains the synthesis of the I-3 monomer of N-methyl structure

[0097] Add 3.612g (0.0384mol) of phenol, 5.746g (0.0416mol) of anhydrous potassium carbonate, 11.69g (0.032mol) and DMF60mL of I-1 monomer of N-methyl structure in the 250mL three-necked flask, nitrogen protection, in Stir at 10°C for 24 hours. After the reaction, the reaction solution was poured into water to precipitate, filtered and dried to obtain the I-3 monomer containing N-methyl structure.

[0098] I-3 monomer containing N-methyl structure (phenoxy in 3 position) 1 H-NMR (DMSO-d 6 , ppm):

[0099] 3.16(s, 6H, CH 3 ), 6.92-7.22(m, 5H, Ar-H), 7.56-7.58(d, 1H, Ar-H), 7.90-7.92(dd, 1H, Ar-H), 8.06-8.08(d, 1H, Ar-H) -H), 8.18-8.20(d, 1H, Ar-H), 8.34-8.36(d, 1H, Ar-H).

[0100] Elemental analysis calculated values: C: 69.90, H: 3.91, N: 6.79, O: 19.40.

[0101] Elemental analysis measured values: C: 69.94, H: 3.90, N: 6.77, O: 19.43.

[0102] I-3 monomer containing N-methyl structur...

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Abstract

The present invention discloses a biphenyl compound that has an asymmetric structure as shown in the formula in the right. The biphenyl imide monomer with an asymmetric structure and the biphenyl dianhydride monomer with an asymmetric structure can be used in the structure of polyimide so as to improve the solubility and the fusibility of the polyimide. The present invention also provides a synthetic method of the asymmetric biphenyl imide monomer, the biphenyl dianhydride and the asymmetric biphenyl dianhydride monomer from the monomers of the category of halogenated phthalimide. The reaction conditions of the method can be easily operated; the products can be easily purified and the economic cost is lower.

Description

technical field [0001] The invention relates to a class of unsymmetrical biphenyl compounds, a preparation method thereof and the technical field of the use of biphenyl dianhydride monomers in the compounds being introduced into the molecular structure of polyimide to improve its solubility and meltability. Background technique [0002] Polyimide (PI) is a high-performance polymer with imide rings in the main chain, among which fully aromatic polyimide is the most eye-catching. Due to their excellent thermal stability, mechanical properties, chemical inertness, dielectric properties, and radiation resistance, polyimides have been used in aerospace in commercial forms such as films, coatings, fibers, plastics, adhesives, and resin-based composites. , electronics industry and other high-tech neighborhoods have been widely used. [0003] [0004] General structural formula of fully aromatic polyimide [0005] Since wholly aromatic polyimide is generally infusible and insol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C07D307/89
Inventor 杨刚
Owner 成都金桨高新材料有限公司
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