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1,3,5-benzenetricarboxylic acid derivative and making method thereof

A technology of trimenetricarboxylic acid and trimenetricarboxylate, applied in coatings, organic chemistry, powder coatings, etc., can solve problems such as inability to completely replace TGIC, inferiority, and limited application range

Inactive Publication Date: 2014-11-19
SHANGHAI YAO HE BIOCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because it is not as good as TGIC in some applications, its use is limited. Except for Europe, which is known for its environmental protection, it cannot completely replace TGIC in other regions.

Method used

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  • 1,3,5-benzenetricarboxylic acid derivative and making method thereof
  • 1,3,5-benzenetricarboxylic acid derivative and making method thereof
  • 1,3,5-benzenetricarboxylic acid derivative and making method thereof

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Embodiment Construction

[0017] A preferred embodiment of the present invention is to first prepare trimethylenetricarboxylate (trimethyl1,3,5-benzenetricarboxylate), and then use trimellitic acid methyl ester to manufacture 1,3,5-tri(2-oxazoline base) ) Benzene (1,3,5-tris(2-oxazolidinyl-2-y1)benzene, hereinafter referred to as TOX-1). The detailed implementation steps and reaction formula are as follows:

[0018] Preparation of trimethyl trimesate

[0019] Take a four-neck bottle, install a mechanical stirrer, a condenser tube and a thermometer, weigh trimesic acid (1.0 equiv), add solvent methanol (7.0 equiv), and heat up to 35-40°C. Add thionyl chloride (3.4 equiv) slowly, control the temperature to 40°C, and stir for 3 hours. Sampling is detected, and the reaction is completed if the content of the starting material is less than 1%. Then the temperature was lowered to 20°C, and a white solid was obtained by suction filtration. Wash the white solid with solvent methanol, and dry it to obtain ...

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Abstract

The invention provides a 1,3,5-benzenetricarboxylic acid derivative and a making method thereof. The 1,3,5-benzenetricarboxylic acid derivative can be used as a curing agent for a polyester powder coating, and has a structural formula as shown in the specification, wherein n is 0, 1 or 2, R1 is H, CH3 or C2H5, and R2 is H, CH3 or C2H5. The making method of the 1,3,5-benzenetricarboxylic acid derivative comprises the following steps: (1) 1,3,5-benzenetricarboxylic acid ester is mixed with ethanolamine with the structural formula as shown in the following structural formula for reaction in a first solvent, R1 and R2 are as defined, the equivalence ratio of ethanolamine to 1,3,5-benzenetricarboxylic acid ester is about 2-5, the reaction temperature is 120 to 200 DEG C, and a white solid product B is obtained; (2) the white solid product B is mixed with thionyl chloride for reaction in a second solvent, the equivalence ratio of thionyl chloride to white solid product B is about 2-4, the reaction temperature is 10 to 50 DEG C, and a product C is obtained; and (3) the product C is mixed with sodium hydroxide for reaction in a third solvent, the equivalent ratio of sodium hydroxide to product C is about 2.5-3.5, the reaction temperature is 30-50 DEG C, and the 1,3,5-benzenetricarboxylic acid derivative is obtained.

Description

technical field [0001] The invention relates to a derivative of trimenetricarboxylic acid and a manufacturing method thereof, in particular to a derivative of trimenetricarboxylic acid used as a curing agent for polyester powder coatings and a manufacturing method thereof. Background technique [0002] Powder coatings are environmentally friendly coatings that have developed rapidly in recent years. Among them, the curing agent for polyester powder coatings is triglycidyl isocyanurate (1,3,5-Triglycidyl isocyanurate, referred to as TGIC) and hydroxyalkylamide (N, N, N', N'-Tetrakis (2 -hydroxyethyl) adipamide (HAA for short) is the most used. [0003] TGIC was developed earlier and has strong functions, but it is irritating to the skin and eyes. In 1991, it was found that it may have carcinogenic and even mutagenic properties. It has long been banned in Europe, but its use still accounts for a large share in other regions. [0004] Due to the toxicity and environmental pol...

Claims

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Application Information

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IPC IPC(8): C07D263/12C09D7/12C09D167/00C09D5/03
CPCC07D263/12C09D7/63
Inventor 洪顺明
Owner SHANGHAI YAO HE BIOCHEM TECH CO LTD
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