Aromatic secondary primary amine containing triaryl-s-triazine structure and ether bond and preparation method thereof

A dibasic primary amine, s-triazine technology, applied in the field of compound synthesis, can solve the problems of high flexibility of ether bonds, decrease of glass transition temperature and thermal decomposition temperature of polymers, etc., to achieve good solubility and thermoplasticity, and reduce dielectric loss. and water absorption, the effect of improving heat resistance

Active Publication Date: 2019-04-16
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the greater flexibility of ether linkages, the glass transition temperature and thermal decomposition temperature of the polymer decreased to some extent.

Method used

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  • Aromatic secondary primary amine containing triaryl-s-triazine structure and ether bond and preparation method thereof
  • Aromatic secondary primary amine containing triaryl-s-triazine structure and ether bond and preparation method thereof
  • Aromatic secondary primary amine containing triaryl-s-triazine structure and ether bond and preparation method thereof

Examples

Experimental program
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preparation example Construction

[0047] The preparation method of the above-mentioned aromatic dibasic primary amine containing triaryl-s-triazine structure and ether bond specifically comprises the following steps in sequence:

[0048] Step 1, add p-aminophenol compounds such as the structure shown in formula (III) (i.e. amine source) and alkali catalyst (the molar ratio of the two is 1.0: (0.1-5.0)), solvent, and dehydrating agent are sequentially added to the A water separator, a stirrer, a thermometer and an inert atmosphere (preferably nitrogen or argon) are introduced into the reactor for reflux reaction for 0.5-8.0 hours, the reaction time is preferably 2 hours, and the dehydrating agent is separated. On the one hand, due to the reaction of p-aminophenol compounds with strong bases (such as sodium hydride, potassium hydride, etc.) to generate water, they will compete with phenoxy salts, resulting in increased side reactions; on the other hand, due to the use of amine sources, bases and solvents Contain...

Embodiment 1

[0058] (1) 0.2mol of 4-aminophenol (that is, R in formula (Ⅲ) 4 and R 5 All hydrogen), 0.14mol of potassium carbonate, 200mL of N-methyl-2-pyrrolidone (NMP) and 200mL of toluene were added into the reaction flask, nitrogen gas was passed, and the toluene was evaporated after reflux with water for 2 hours.

[0059] (2) Cool the reaction flask to room temperature, add 0.1mol 2,4-bis(4-fluorophenyl)-6-phenyl-1,3,5 triazine (BFPT, that is, R in formula (II) 1 and R 2 , R 3 Both are hydrogen), heated to 160°C for 12h, and cooled to room temperature.

[0060] (3) Precipitate the product in cold water, filter (recover the mother liquor, and recycle), collect the solid, and repeatedly rinse with warm water several times to remove inorganic salts and solvents.

[0061] (4) Collect the filter cake and dry it under vacuum to obtain 49.6g of tan 2,4-two 4-(4-aminophenoxy)phenyl-6-phenyl-1,3,5-triazine product (the structure is as follows: shown), the molar yield was 94.6%, and the pu...

Embodiment 2

[0079] (1) Add 0.2 mol of 3,5-dimethyl-4-aminophenol, 0.2 mol of sodium hydroxide, 100 ml of N-methylpyrrolidone (NMP) and 50 ml of toluene into the reaction flask, ventilate nitrogen, and bring water under reflux After reacting for 2h, toluene was distilled off.

[0080] (2) Cool the reaction flask to room temperature, add 0.1mol 2,4-bis(3,5-dimethyl-4-fluorophenyl)-6-phenyl-1,3,5 triazine, and heat up to React at 160°C for 12h, then cool to room temperature.

[0081] (3) Precipitate the product in cold water, filter (recover the mother liquor, and recycle), and repeatedly rinse with warm water several times to remove inorganic salts and solvents.

[0082] (4) Collect the filter cake and dry it in vacuum to obtain tan 2,4-bis[3,5-dimethyl-4-(3,5-dimethyl-4-aminophenoxy)phenyl]-6- The phenyl-1,3,5-triazine product (structure shown in the following formula) has a molar yield of 91.5% and a purity of 99%.

[0083]

[0084] R in the structure 1 ~R 2 , R 4 ~R 5 Both are ...

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Abstract

The invention discloses aromatic primary diamine containing a triaryl-s-triazine structure and an ether bond and a preparation method thereof, belonging to the technical field of synthesis of compounds. The aromatic primary diamine containing the triaryl-s-triazine structure and the ether bond has a structural formula as shown in a formula (I). The preparation method comprises the following steps: subjecting a dihalogen compound containing triaryl-s-triazine and shown in a formula (II) and a p-aminophenol compound as shown in a formula (III) to a nucleophilic substitution reaction; and then subjecting a reaction product to filtering, washing and drying so as to obtain the aromatic primary diamine containing the triaryl-s-triazine structure and the ether bond. The aromatic primary diamine containing the triaryl-s-triazine structure and the ether bond in the invention contains the triaryl-s-triazine structure with high rigidity, high thermal stability and strong polarity, so when the aromatic primary diamine is used as a monomer for synthesis of polyamide, polyimide and benzoxazine resin, the aromatic primary diamine can effectively improve the heat resistance and mechanical properties of a material and reduce the dielectric loss and water absorption rate of the material at the same time.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and relates to a s-triazine derivative and a preparation method thereof, in particular to an aromatic secondary primary amine containing a triaryl-s-triazine structure and an ether bond and a preparation method thereof. Background technique [0002] Aromatic primary diamines are one of the important raw materials for the synthesis of polyamide, polyimide, and benzoxazine resins, and are also commonly used curing agents for epoxy resins and phthalonitrile resins. Commonly used aromatic dibasic primary amines mainly include diaminodiphenyl sulfone (thermal decomposition temperature 280°C, melting point 175-181°C), diaminodiphenyl ether (thermal decomposition temperature 246°C, melting point 190-193°C) and diaminodiphenyl Methane (thermal decomposition temperature 242°C, melting point 89-90°C), etc. However, because these three diamines are easy to sublimate, they are easy to escape from...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D251/24C08G73/06C08G73/10C08G59/50
CPCC07D251/24C08G59/5086C08G73/0638C08G73/1085
Inventor 蹇锡高宗立率王锦艳刘程张守海
Owner DALIAN UNIV OF TECH
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