Preparation method of photosensitive biphenyl diamine monomer

A biphenylenediamine and photosensitivity technology, which is applied in the field of preparation of photosensitive biphenylenediamine monomers, can solve the problems of limited types of graft polymers, great difficulty in industrialization, reduced product yield and the like, and achieves a simple synthesis method. Safe, continuous preparation, the effect of improving productivity

Active Publication Date: 2022-03-18
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the disadvantages of this method are that the types of grafted polymers are limited, the cost is high and time-consuming, and the industrialization is difficult
[0007] The potassium hydroxide reagent used in the preparation of compound 1 from photosensitive benzidinediamine monomer by this method has a strong alkalinity, and long-term use will cause certain damage to the equipment; while the nitric acid used in the preparation of compound 2 will destroy it to a certain extent. The alkyl chain structure in compound one reduces the product yield; in addition, iron powder was used as a reducing agent in the preparation of compound three. device, and the agitation of iron powder will cause a certain degree of damage to the equipment due to friction with the inner wall of the equipment

Method used

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  • Preparation method of photosensitive biphenyl diamine monomer
  • Preparation method of photosensitive biphenyl diamine monomer
  • Preparation method of photosensitive biphenyl diamine monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1 A kind of preparation method of photosensitive biphenyl diamine monomer

[0032] The synthetic route of photosensitive biphenyl diamine monomer is as follows:

[0033]

[0034] The preparation method is carried out in the following order of steps:

[0035] (1): Synthesis of compound A (2,2'-dinitro-4,4'-dihydroxybiphenyl)

[0036] When the 4,4'-dihydroxyl group is directly nitrated, due to the electron-donating effect of the phenolic hydroxyl group, it will directly introduce two nitro groups at the 3,3' position, and if you want to introduce two nitro groups at the 2,2' or 2,3' position The nitro group needs to change the electron-donating effect of the position of its phenolic hydroxyl group, so p-nitrobenzenesulfonyl chloride is used to react with the phenolic hydroxyl group to generate a strong electron-withdrawing p-nitrobenzenesulfonyl group, and the strong electron-withdrawing property of the newly generated group It can make the 2,2' position i...

Embodiment 2

[0060] Embodiment 2 A kind of preparation method of photosensitive biphenyl diamine monomer

[0061] The synthetic route of photosensitive biphenyl diamine monomer is as follows:

[0062]

[0063] The preparation method is carried out in the following order of steps:

[0064] (1): Synthesis of compound A (2,3'-dinitro-4,4'-dihydroxybiphenyl)

[0065] a1. Add 9.3g of 4,4'-dihydroxybiphenyl and 5g of sodium bicarbonate into a single-necked bottle filled with 200ml of ethanol in an ice-water bath, and add 6g of p-nitrobenzenesulfonyl chloride at a rate of 1 drop / second under magnetic stirring Slowly added dropwise to the reaction system;

[0066] a2. At 0°C, stir magnetically and react for 12 hours, then filter the ethanol and wash the product with 200 ml of deionized water three times to obtain 18.1 g of the crude intermediate product A-1;

[0067] a3. Slowly add 70ml of dilute nitric acid with a mass fraction of 68% into the one-necked bottle, place it in an ice-water bat...

Embodiment 3

[0088] Embodiment 3 A kind of preparation method of photosensitive biphenyl diamine monomer

[0089] The synthetic route of photosensitive biphenyl diamine monomer is as follows:

[0090]

[0091] according to figure 1 It can be seen that the structure of the photosensitive biphenylenediamine monomer prepared by this method is consistent with the structure of the final product of the design route through the comparison of the chemical shift of the specific characteristic proton and the corresponding integral value, which strongly proves that The practicability of the photosensitive biphenyl diamine monomer synthesis method proposed by the present invention;

[0092] according to figure 2 As shown, the prepared photosensitive biphenyl diamine monomer has high thermal stability no matter in the nitrogen atmosphere or in the air atmosphere. When the ambient temperature reaches 210 ° C, the thermal stability of the photosensitive diamine monomer The weight loss is only abou...

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PUM

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Abstract

The invention discloses a preparation method of a photosensitive biphenyl diamine monomer. The preparation method comprises the following steps: (1) using 4,4'-dihydroxybiphenyl as a starting material, , 2, 3' and 3, 3' any one position introduces a nitro group to prepare compound A; (2) introduces a halogenated linear alkyl group with a halogen terminal at the hydroxyl position of compound A to prepare Compound B is obtained; (3) In the reaction environment with a reducing agent, the nitro group in the compound B is reduced to an amino group to obtain the compound C; (4) In the reaction environment with a Lewis base, the compound C containing The photosensitive group of the hydroxyl group is used to replace the halogen group at the end of the halogenated straight-chain alkyl group on the compound C, thereby preparing a photosensitive biphenyl diamine monomer. The synthesis method of the photosensitive biphenyl diamine monomer provided by the invention is simpler and safer, has higher controllability and a more considerable yield, and is suitable for stable and continuous mass production of the photosensitive biphenyl diamine monomer.

Description

technical field [0001] The invention belongs to the technical field of compound organic synthesis, and in particular relates to a preparation method of a photosensitive biphenyl diamine monomer. Background technique [0002] Polyimide has outstanding heat resistance and product dimensional stability, and its mechanical properties are excellent, and its dielectric and insulating properties are good. In addition, the coefficient of thermal expansion of polyimide is very low (12-20ppm, 1ppm=10 -6 K -1 ), which is similar to the thermal expansion coefficient of metal copper wire (about 17.7ppm), which makes polyimide have great application prospects in the field of flexible printed circuit boards. Polyimide is often used as a substrate or protective layer in flexible printed circuit boards. Traditional polyimide flexible circuit boards often use photoresist lithography and nanoimprinting techniques, but the process is complex and metal materials Low utilization rate, high po...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/90C07C303/28C07C303/30C07C309/73C07C201/12C07C205/21C07C205/37C07C213/02C07C217/84
CPCC07D211/90C07C303/28C07C303/30C07C201/12C07C213/02C07C201/08C07C309/73C07C205/21C07C205/37C07C217/84
Inventor 陈旭东钟世龙洪炜
Owner SUN YAT SEN UNIV
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