A kind of preparation method of multifunctional synergistic antioxidant stabilizer

An antioxidant stabilizer, multi-functional technology, applied in the preparation of organic compounds, chemical instruments and methods, preparation of aminohydroxy compounds, etc., can solve problems such as damage, color damage, embrittlement and cracking

Active Publication Date: 2017-05-10
SHAOXING RUIKANG BIOTECHNOLOGES CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The anti-oxidation and stabilizing additives currently used in the market have small molecular weight, are easily volatile or degraded, and have uneven distribution in the material, so that the material will be damaged during processing or use, especially under high temperature and strong light irradiation conditions. Cause problems such as short service life, color damage, weakened strength or brittle cracking

Method used

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  • A kind of preparation method of multifunctional synergistic antioxidant stabilizer
  • A kind of preparation method of multifunctional synergistic antioxidant stabilizer
  • A kind of preparation method of multifunctional synergistic antioxidant stabilizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1. Structural formula

[0038]

[0039] 2. Synthetic route:

[0040]

[0041] 3. Synthesis step 1 of 4-bromomethyl-2,6-di-tert-butylphenol (intermediate 1):

[0042] 5 g of 2,6-di-tert-butyl-p-cresol (22.69 mmol) dissolved in CCl 4 or CHCl 3 Or dichloromethane or THF or toluene and other solvents (20-50 milliliters), under nitrogen protection and ultraviolet lamp (mercury lamp 350 watts) irradiation, drop liquid bromine (1.2-1.5 mmol) above solvent solution (15-50 milliliter), the rate of addition can be determined with the speed of the reaction, and TLC monitors the reaction process.

[0043] Stir for 5-20 minutes after the titration, remove the organic solvent under vacuum, and use the oily product directly in the next step.

[0044] 4. Synthesis step 2 of 4-bromomethyl-2,6-di-tert-butylphenol (intermediate 1):

[0045] 5.0 g of 2,6-di-tert-butyl-p-cresol (22.69 mmol) was dissolved in CCl 4 or CHCl 3 Or in solvents (25-50 milliliters) such as dichlorometh...

Embodiment 2

[0050] 1. Structural formula

[0051]

[0052] 2. Synthetic route:

[0053]

[0054] 3. Preparation of Intermediate 1:

[0055] Add 6.1 g of mercaptan (42.30 mmol) dropwise to 3 g of 2,2-dichloroethylamine (21.12 mmol) and 10-50% KI of THF or acetone or acetonitrile or dichloromethane or ethanol, etc. (1 : 5-20, w / v) solution, the mixture was heated to 40-70° C., reacted for 3-9 hours, TLC monitored the reaction progress until the reaction was complete. The organic solvent was removed in vacuo, NaCl aqueous solution and dichloromethane or ethyl acetate were added, mixed well, the organic phase was separated, and the aqueous phase was extracted twice. Anhydrous Na 2 SO 4 The organic phase was dried, filtered and intermediate 1 was used directly in the next step after concentration.

[0056] 4. Preparation of Intermediate 2:

[0057] 5.93 g of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid (21.30 mmol) was dissolved in dry THF or dichloromethane or ethyl acetate...

Embodiment 3

[0062] 1. Structural formula

[0063]

[0064] 2. Synthetic route:

[0065]

[0066] 3. Synthesis step 1 of 2,2,6,6-di-tert-butyl-4-bromomethylphenol (intermediate 1):

[0067] 5 grams of 2,2,6,6-di-tert-butyl-p-cresol (27.11 mmol) was dissolved in CCl4 or CHCl3 or CH2Cl2 or THF or chlorobenzene or toluene or dibromoethane solvent (1:5-20, w In / v), under the protection of nitrogen, a solution of the same volume of bromine (28.01-37.57 mmol) was added dropwise under the irradiation of a 350-watt mercury lamp, and the reaction progress was monitored by TLC. After the dropwise addition, the mixture was stirred for 5-40 minutes, and the organic solvent was removed under vacuum to obtain a light reddish-brown oil, which was directly used in the next reaction, with a yield of 95-100%.

[0068] 4. Synthesis step 2 of 2,2,6,6-di-tert-butyl-4-bromomethylphenol (intermediate 1):

[0069] 5 g of 2,2,6,6-di-tert-butyl-p-cresol (27.11 mmol) dissolved in CCl 4 or CHCl 3 or CH 2...

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Abstract

The invention relates to a preparation method and application of a multifunctional hybrid synergistic multifunctional synergistic antioxidant stabilizer formed by stable connection of ether bond, thioether bond, amine and amide bond, comprising the following steps: alcohol or thiol or amine Add NaH or NaOH in anhydrous THF, DMF, acetone, ethyl acetate or acetonitrile solvent under nitrogen protection, stir, add iodide, bromide or chloride with NaI or KI or activated alcohol dropwise, stir Or heating; add saturated NH4Cl aqueous solution and organic solvent, extract, Na2OS4 dry the organic phase, filter, remove the organic solvent; obtain solid product, purify oily or liquid product. The invention has the advantages of stable bonded multifunctional hybrid synergistic properties, heat resistance, light resistance, high temperature processing resistance, hydrolysis resistance, acid and alkali resistance, etc., which makes up for the weakness of similar products in the current market and provides a new way for the development of new products. A generation of potent antioxidant stabilizers lays the foundation.

Description

technical field [0001] The invention relates to a preparation method of a multifunctional hybrid synergistic anti-oxidation stabilizer linked by an ether bond or a thioether bond or an amine bond or an amide bond. It is a new material anti-oxidation stability additive and can be directly applied to polymer materials as a quality guarantee It is an anti-oxidation and stabilizing additive that maintains color and function, and is used in a series of products such as plastics, rubber, fibers, coatings, paints and petroleum. Background technique [0002] The global sales market of anti-oxidation and stabilizing additives is very large. In 2011, the global consumption of a single plastic antioxidant was about 420,000 tons. At present, the Asia-Pacific region has the largest consumption, followed by Europe and North America. It is estimated that the sales of material antioxidant stabilizers in the Asia-Pacific region will reach 4.8 billion US dollars in 2016. [0003] The demand ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08K5/13C08K5/375C08K5/3492C08K5/17C08K5/3435C08G73/06C08L79/04C09D7/12C07C43/178C07C41/16C07C323/41C07C319/20C07D251/70C07C215/50C07C213/04C07D211/58
Inventor 毛丽娟刘树柏杨平胜申丽丽谢煜樵康舒朱新兵赵晶晶屠红燕
Owner SHAOXING RUIKANG BIOTECHNOLOGES CO INC
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