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Double-hindered phenol structure-contained hydrazides compound and preparation method thereof

A technology of ester compounds and hydrazides, which is applied in the field of hydrazide compounds containing double hindered phenol structure and their preparation, can solve the problems of compatibility, yellowing resistance, migration resistance and anti-oxidation ability, low molecular weight, etc. problems, to achieve the effect of enhancing thermal oxidation resistance, increasing molecular weight, and easy availability of raw materials

Active Publication Date: 2014-05-07
YANTAI RUILONG CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, due to the low molecular weight of traditional antioxidants or hydrazide anti-yellowing agents, there are many deficiencies in compatibility, anti-yellowing, anti-migration and anti-oxidation capabilities.

Method used

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  • Double-hindered phenol structure-contained hydrazides compound and preparation method thereof
  • Double-hindered phenol structure-contained hydrazides compound and preparation method thereof
  • Double-hindered phenol structure-contained hydrazides compound and preparation method thereof

Examples

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Effect test

Embodiment 1

[0037] (1) Add 150g of 2-methyl-6-tert-butylphenol and 5g of sodium hydroxide into a four-neck flask equipped with mechanical stirring, thermometer and constant pressure titration funnel, heat, wait until the temperature rises to 110°C, and keep warm for reaction After 1 hour, 84 g of α,β-methyl acrylate was slowly added dropwise, and the temperature during the dropwise addition was controlled at 115-120°C. After the dropwise addition, the reaction was incubated for 4 hours. The temperature of the reaction solution drops below 80°C, add 200g of toluene to the four-neck flask to dilute, neutralize the reaction solution with dilute sulfuric acid until the pH is 5~6, then separate the water layer, and wash the organic layer with water until the pH is 6. Stand still, separate layers, recover toluene by distillation under reduced pressure, and fractionate under reduced pressure to obtain 185 grams of methyl 3-methyl-4-hydroxy-5-tert-butylpropionate, off-white molten cast body, ...

Embodiment 2

[0044] (1) Add 150g of 2-methyl-6-tert-butylphenol and 5g of sodium ethoxide into a four-necked flask equipped with a mechanical stirrer, a thermometer, and a constant pressure titration funnel, and heat it until the temperature rises to 110°C and keep it warm for 1h , and then slowly add α,β-ethyl acrylate 90g dropwise, and the temperature during the dropping process is controlled at 115-120°C. After the dropwise addition, the reaction was incubated for 4 hours. The temperature of the reaction solution drops below 80°C, add 200g of toluene to the four-neck flask to dilute, neutralize the reaction solution with dilute sulfuric acid until the pH is 5~6, then separate the water layer, and wash the organic layer with water until the pH is greater than 6. Stand still, separate layers, recover toluene by distillation under reduced pressure, fractional distillation under reduced pressure to obtain 195 grams of ethyl 3-methyl-4-hydroxy-5-tert-butylpropionate, off-white molten cast bo...

Embodiment 3

[0049] (1) Add 150g of 2-methyl-6-tert-butylphenol and 6g of potassium hydroxide into a four-neck flask equipped with a mechanical stirrer, a thermometer and a constant pressure titration funnel, and heat it until the temperature rises to 110°C, and keep it warm for reaction After 1 hour, slowly add 90 g of α,β-methyl acrylate dropwise, and the temperature during the dropping process is controlled at 115-120°C. After the dropwise addition, the reaction was incubated for 4 hours. The temperature of the reaction solution drops below 80°C, add 200g of toluene to the four-neck flask to dilute, neutralize the reaction solution with dilute sulfuric acid until the pH is 5~6, then separate the water layer, and wash the organic layer with water until the pH is just greater than 6. After standing still and stratifying, recover toluene by distillation under reduced pressure, fractional distillation under reduced pressure to obtain 187 grams of methyl 3-methyl-4-hydroxy-5-tert-butylpropio...

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Abstract

The invention discloses a double-hindered phenol structure-contained hydrazides compound for a light stabilizer and a preparation method thereof. The double-hindered phenol structure-contained hydrazides compound has a double-hindered phenol and double-hydrazide structure, thus, the molecular weight is increased, and the migration resistance and thermal oxidation resistance capacity is strong. The preparation method comprises the following steps: performing addition reaction on hindered phenols and alpha, beta-acrylic ester under the action of a catalyst to obtain an addition product, wherein the molar ratio of the hindered phenols to the alpha, beta-acrylic ester is 1.0:(0.6-1.8), and the catalyst is alkali metal, an alkali metal hydroxide, an alkali metal hydride or an alkali metal alcoholate; then, performing carbonyl nucleophilic substitution reaction on the addition product and a hydrazine hydrate in an organic solvent A to obtain a hydrazides substitution product, wherein the molar ratio of the addition product to the hydrazine hydrate is 1.0:(0.8-5.0); performing the reaction between a diisocyanate compound and the hydrazides substitution product at the temperature of 0-10 DEG C; and carrying out recrystallization to obtain a goal product. By adopting the preparation method disclosed by the invention, the operation is simple, the raw materials are available, and the cost is low.

Description

technical field [0001] The invention relates to a hydrazide compound used as an anti-oxidation anti-yellowing agent and a preparation method thereof, in particular to a hydrazide compound containing a double hindered phenol structure and a preparation method thereof. Background technique [0002] Hindered phenolic compounds can inhibit the oxidative and thermal degradation of many organic compounds and polymers because they can capture peroxyl radicals. They are the most widely used antioxidants in the polymer industry, such as CIBA's antioxidants IRGANOX-1010, IRGANOX-245, IRGANOX-1076, antioxidant 1790 from CYTEC, USA, etc. Antioxidants are additives that inhibit or slow down the degradation of polymer materials due to oxidation. Therefore, the addition of antioxidants can effectively improve the heat resistance, light resistance, and oxidation resistance of polymer materials, and prolong the outdoor service life. [0003] Hydrazide anti-yellowing agents such as bis-(N,N...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C243/32C07C241/04C08L23/12C08K5/25
Inventor 姚建文王玉林
Owner YANTAI RUILONG CHEM TECH CO LTD