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A kind of preparation method of urea linkage multifunctional synergistic antioxidant stabilizer

An antioxidant stabilizer, multifunctional technology, applied in the preparation of organic compounds, chemical instruments and methods, preparation of carbamate derivatives, etc., can solve the problems of weakening strength, embrittlement cracking, damage, etc. The effect of improving the use value

Active Publication Date: 2017-04-12
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 urea linkage multifunctional synergistic antioxidant stabilizer
  • A kind of preparation method of urea linkage multifunctional synergistic antioxidant stabilizer
  • A kind of preparation method of urea linkage multifunctional synergistic antioxidant stabilizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1. Synthetic route:

[0037]

[0038] 2. The chemical structural formula of the product:

[0039]

[0040] 3. Preparation method:

[0041] 2 g of isophorone diisocyanate (8.99 mmol) and 2.18 g of 2,6-di-tert-butyl-p-cresol (9.89 mmol) were dissolved in 20 ml of dry acetone, and 0.03 g of KOH was added under nitrogen protection. The mixture was stirred at room temperature for 30 minutes and heated to 50°C for 18 hours. The reaction was monitored by TLC until the diisocyanate disappeared in the reaction system. The reaction was cooled to room temperature and stirred at room temperature for 3 hours. Remove acetone under vacuum, add EtOAc and saturated NaCl as a solution, extract the product to the organic phase (20mlx3), dry the organic phase with anhydrous Na2SO4, filter, and concentrate the filtrate under vacuum, in a mixed solvent of EtOAc and petroleum ether (5 : 3) to obtain a white or light yellow solid. 1 H NMR(400MHz,DMSO-d6),δ(ppm):7.13(s,1H,CH),7.03(s,1H,...

Embodiment 2

[0043] 1. Synthetic route:

[0044]

[0045] 2. The chemical structural formula of the product:

[0046]

[0047] 3. Preparation method:

[0048] 2 g of toluene 2,4-diisocyanate (11.48 mmol) was dissolved in 20 ml of dry acetone or acetonitrile or dry toluene and 10% (w / w) triethylamine or NaOH or DBU, and added 2,6- Di-tert-butyl-p-cresol (8.86 g, 40.19 mmol). The mixture was stirred at room temperature for 20 minutes, stirred at 50 degrees Celsius for 18 hours, cooled to room temperature, added petroleum ether (10ml) and stirred at room temperature for 10 minutes, filtered the precipitated solid, and reconstituted in a mixed solvent of ethyl acetate-petroleum ether (1:1). Crystallization gave 3.97 g of white powder, with a yield of 65.0%.

[0049] 1 H NMR (400MHz, DMSO-d6), d (ppm): 7.16-7.41 (m, 3H, 3CH), 6.91 (s, 2H, 2CH), 6.69 (s, 2H, 2CH), 3.35 (s, 3H, CH3), 2.50 (m, DMSO), 2.28 (s, 3H, CH3), 2.18 (s, 3H, CH3), 1.31-1.42 (m, 36H, 12CH3).

Embodiment 3

[0051] 1. Synthetic route:

[0052]

[0053] 2. The preparation method of 1,6-hexamethylene diisocyanate (intermediate 1):

[0054] Dissolve 5 g of 1,6-hexanediamine (43.03 mmol) in 20 ml of dry toluene or dichloromethane or THF or acetone, cool with ice water until 0-5 degrees Celsius, add trichlorodimethyl carbonate dropwise under nitrogen protection The solution (1:5, w / v), was stirred for 20 minutes, and 4.4 g (43.08 mmol) of triethylamine was added dropwise. The mixture was stirred at 0-10°C for 30 minutes, warmed to room temperature and stirred for 1 hour. Add 20ml EtOAc, wash the organic phase with 0.1N ice-water hydrochloric acid (20ml x3), and wash once with NaCl aqueous solution. The organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated (yield 96%) and directly used in the next reaction.

[0055] 3. The chemical structural formula of the product:

[0056]

[0057] 4. The preparation method of the product:

[005...

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PUM

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Abstract

The present invention relates to the preparation method of urea bonded multifunctional synergistic antioxidant stabilizer, comprising the following steps: (1) organic amine is added to dry dichloromethane or toluene of trichloromethyl carbonate at zero degree, NEt3 is added dropwise, and the reaction is complete Afterwards, the aqueous hydrochloric acid solution washes away the organic base, dries the organic phase, concentrates and purifies by chromatography to obtain the expected intermediate or directly uses it in the next step after concentration; (2) isocyanate is dissolved in solvents such as dry dichloromethane or toluene, and added to 2,6-di-tert-butyl-p-cresol or added to 4-amino-2,2,6,6-tetramethylpiperidine and other reactants with stirring. After the reaction was complete, it was concentrated in vacuum and purified to obtain the product. The anti-oxidation stabilizer of the present invention has the properties such as the multifunctional hybrid synergistic properties of stable bonding, heat resistance, light resistance, high temperature processing performance, hydrolysis resistance, acid and alkali resistance, and corrosion resistance. These advantages make up for The weakness of similar products in the current market lays the foundation for the development of a new generation of effective antioxidant stabilizers.

Description

technical field [0001] The invention relates to a preparation method of urea as a bonded segment to form a multifunctional hybrid synergistic anti-oxidation stabilizer. It is a new type of anti-oxidation stabilizing additive for polymer materials, which can be directly applied to polymer materials as an anti-acid, anti-alkali, Anti-hydrolysis quality, color, and function-maintaining anti-oxidation and stabilizing additives, used in plastics, rubber, fibers, coatings, paints, and petroleum products. 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 and production of anti-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/58C07C271/58C07C269/02C08K5/3435C08K5/205C09D7/12C09D5/00
Inventor 毛丽娟刘树柏萨弗瑞兹阿麦德杨平胜谢苗苗
Owner SHAOXING RUIKANG BIOTECHNOLOGES CO INC
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