Preparation of 3,3’5,5′-tetramethylbiphenyl bisphenol diglycidyl ether_Kain Industrial Additive

Background and overview^[1][2]

Electronic materials are the basis for the development of the microelectronics industry. As the main structural material for the production of integrated circuits, epoxy plastic sealants are also developing rapidly with the development of chip technology, and the development of plastic sealant technology will greatly promote the microelectronics industry. development of. Biphenyl epoxy resin, especially 3,3’5,5′-tetramethylbiphenyl bisphenol diglycidyl ether, has low viscosity, good adhesion, good solubility and high toughness, so it is promising It is widely used in epoxy molding compounds with high filling technology.

Physical and chemical properties and structure^[1]

3,3’5,5′-Tetramethylbiphenylbisphenol diglycidyl ether is a light yellow crystal. It is solid at room temperature and easily turns into powder. However, the molten viscosity becomes very high above the melting point. Low. It is characterized by low melt viscosity, low moisture, and high adhesion. It can be filled with a large amount of spherical silica filler powder to reduce the thermal expansion coefficient. The biphenyl group contained in its main chain is a highly rigid and heat-resistant group. The nearly planar structure of the biphenyl group increases the regularity of the chain and the intermolecular force, and increases physical cross-linking in the isotropic network. Density, its cured product has good heat resistance and high Tg transition temperature. The four methyl groups it carries make it have greater steric hindrance, making it relatively difficult for the movement of macromolecular segments in the cured network, increasing the dynamic mechanical properties, and having good toughness, low viscosity, and high filling. sex. It has a wide range of application prospects.

3,3’5,5′-Tetramethylbiphenylbisphenol diglycidyl ether

Preparation^[2]

The traditional method of preparing 3,3’5,5′-tetramethylbiphenyl bisphenol diglycidyl ether is mainly prepared by the NaOH one-step method. However, in order to obtain a product with an epoxy equivalent close to the theoretical value, the addition of NaOH The method is strict and the post-reaction processing is cumbersome.

Take 10mL of isopropyl alcohol, 110g of epichlorohydrin, 14.52g of 3,3′,5,5′-tetramethyl-4,4′-biphenyldiol, and 0.15g of tetrabutylammonium bromide. Stir and react with nitrogen at 90°C for 10 hours. Add dropwise a solution containing 8g of sodium hydroxide with a concentration of 30%. At the same time, excess epichlorohydrin is evaporated under reduced pressure. After the dropwise addition, stir the reaction for 30 minutes and rinse twice with cold water. After suction filtration, recrystallize it twice with a methanol/acetone (2:1 volume ratio) mixed solution. After the activated carbon fades, vacuum drying at 70°C gives light yellow 3,3’5,5′-tetramethylbiphenyl bisphenol bisphenol. Glycidyl ether 24.84g. Yield: 86%, epoxy equivalent: 189g/mol, melting point: 104-106°C.

Main reference materials

[1] Zhang Pengyun, Chen Weidong, Yang Wenlong, Li Chunxin, & Liu Yin. (2011). 4,4′-bis(4-hydroxybenzyloxy)-3,3′,5,5′-tetramethyl Synthesis of biphenyl diglycidyl ether. Fine and Specialty Chemicals (06), 39-41.

[2] Chen Weidong. (2011). Research on the development of biphenyl diphenol series products and the synthesis of biphenyl liquid crystal materials. (Doctoral dissertation, Northwest Normal University).

[3] Ren Shaoping, Lu Mangeng, Ling Youdao, & Zheng Yiquan. (0). Preparation of a 3,3′,5,5′-tetramethyl-4,4′-biphenyl diglycidyl ether Method.