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Novel chelate-polymer antioxidative stabilizer, preparation method therefor and application of novel chelate-polymer antioxidative stabilizer

An anti-oxidative stabilizer and anti-oxidation technology, applied in chemical instruments and methods, thioether preparation, organic chemistry, etc., can solve problems such as increasing environmental pollution, affecting the use function and life of polymer materials, and threats to life safety. The effect of good matching, maintaining mechanical properties, and improving protection performance

Inactive Publication Date: 2019-11-12
SHAOXING RUIKANG BIOTECHNOLOGES CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This not only seriously affects the function and life of polymer materials, increases environmental pollution, but also poses a potential threat to our life safety

Method used

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  • Novel chelate-polymer antioxidative stabilizer, preparation method therefor and application of novel chelate-polymer antioxidative stabilizer
  • Novel chelate-polymer antioxidative stabilizer, preparation method therefor and application of novel chelate-polymer antioxidative stabilizer
  • Novel chelate-polymer antioxidative stabilizer, preparation method therefor and application of novel chelate-polymer antioxidative stabilizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The structural formula of target product 1

[0023]

[0024] Synthesis of target product 1:

[0025] Step (1): preparation of bisphenol A diglycidyl ether (compound 2);

[0026] Add 1mol (ie 228g) of bisphenol A and 2.8mol (ie 260g) of epichlorohydrin into a 2-liter three-necked flask, add a reflux tube, protect with N2, heat and stir at 70°C, when the internal temperature reaches 65°C, divide into 4 batches Slowly add 2.05mol (ie 82g) sodium hydroxide, keep warm until the reaction of bisphenol A is completed, add 1L MTBE after cooling down to 50°C, filter the insoluble matter, and recover MTBE and epichlorohydrin from the filtrate under reduced pressure to obtain colorless The oily substance, 306 g of bisphenol A diglycidyl ether, was directly used in the next step without further purification.

[0027] Step (2) synthesis of target product 1;

[0028] When compound 2 is bisphenol A bisglyceryl ether, the thiol is n-dodecanethiol.

[0029] Add 0.20 mol (ie 38.2 g...

Embodiment 2

[0031] Chemical synthesis target product 2 Example synthesis steps:

[0032] Target Product 2 Structural Formula

[0033]

[0034] Target product 2 synthesis steps:

[0035] When compound 2 is bisphenol F bisglyceryl ether, the thiol is n-dodecanethiol, if m=2.0, n=0. The reaction steps are: add 313 grams of bisphenol F bisglyceryl ether, 1200 ml of anhydrous dichloromethane or dichloroethane or acetone or acetonitrile into a 2.5L reaction bottle, stir until dissolved, add n-dodecanethiol 405 gram, nitrogen protection, ice bath for half an hour, slowly add 5 grams of sodium hydroxide, naturally warm up to room temperature and then insulate and stir for 20 hours, detect that the mercaptan reaction is complete, reclaim dichloromethane under reduced pressure, freeze to obtain 715 grams of white solid, and produce The rate is 99.6%.

[0036] (ESI / MS+: 493.71, 515, 739.6, 827.5, 1029.48; 1 H-NMR / 400MHZ, CDCl 3 :δ7.11–7.03(m,1H),6.83(ddd,J=8.6,4.3,2.2Hz,1H),4.05–3.89(m,2H),2...

Embodiment 3

[0038] Chemical synthesis target product 3 example synthesis steps:

[0039] Target Product 3 Structural Formula

[0040]

[0041] Target product 3 synthesis steps:

[0042] When compound 2 is triglycidyl isocyanurate (TGIC), and the thiol is n-dodecanethiol, add 29.7 grams of TGIC, 120 ml of anhydrous ethyl acetate or anhydrous dichloromethane or anhydrous dichloromethane to a 250ml reaction bottle. Ethyl chloride, stirred until dissolved, added 60.7 grams of n-dodecanethiol, under nitrogen protection, slowly added 0.5 grams of sodium hydroxide, stirred at room temperature for 16 hours, detected that the mercaptan reaction was complete, filtered to obtain 90 grams of white solid, and the yield 99.6%.

[0043] ESI / MS+: 904.52, 701.98; 1 H-NMR / 400MHZ, CDCl 3:δ6.54(s,1H),4.18–3.80(m,1H),2.79–2.37(m,1H),1.98(s,1H),1.51(p,J=7.4Hz,1H),1.19(s ,6H),0.81(t,J=6.7Hz,1H).

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PUM

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Abstract

The invention belongs to the fields of structural design and synthesized preparation of innovative chelate polymer-material antioxidants and particularly relates to an application of a novel chelate antioxidative stabilizer in a high-polymer material and a preparation method for the novel chelate antioxidative stabilizer. The novel chelate antioxidative stabilizer acts dual protective actions. Thepreparation method for the chelate antioxidative stabilizer comprises the steps: (1) adding a compound 1 and epoxy chloropropane, slowly adding sodium hydroxide or potassium hydroxide in batches, carrying out a heat-preserving reaction until the compound 1 reacts fully, and adding 1L of MTBE or DCM or DCE, so as to obtain a colorless oily compound 2; and (2) adding thioalcohol, adding a solvent,carrying out stirring for 30 minutes, adding the compound 2 at the temperature of 5 DEG C to 10 DEG C under nitrogen protection, carrying out ice-bath treatment for half an hour, and slowly adding sodium hydroxide or potassium hydroxide, thereby obtaining a compound 3 or a compound 4. The chelate antioxidative stabilizer not only has a thioether long-acting high-temperature oxidation resisting activity functional group, but also has the function of forming sulfur and hydroxyl coordinated five-membered cyclic complexed metal ions, and this function plays a role in complexed removal of metal ions catalyzing degradation of the high-polymer material.

Description

technical field [0001] The invention belongs to the field of preparation of polymer material functional additives, in particular to a novel chelating anti-oxidation stabilizer and a preparation method thereof. Background technique [0002] Antioxidant stabilizers for polymer materials, also known as antioxidants, are a class of functional additives that can quickly help capture and neutralize free radicals when polymer materials are oxidized, thereby eliminating free radicals and preventing oxidative degradation of polymer materials. When it only exists in a small amount in the polymer system, it can delay or inhibit the oxidation process of the polymer, thereby preventing the aging of the polymer, maintaining its original properties, and designing or extending its service life as required. Sulfur-containing organic compound auxiliary antioxidants have become an important long-term high-temperature antioxidant in auxiliary antioxidants because they can effectively decompose ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K15/12C09K15/30C07C319/14C07C323/12C07C323/52C07D405/06C07D251/30C08K5/375C08K5/378C08K5/41
CPCC07C319/14C07C323/12C07C323/52C07D251/30C07D405/06C08K5/375C08K5/378C08K5/41C09K15/12C09K15/30
Inventor 毛丽娟尹奇伟王以菲赵城世罗瑞王纪江陈秀颖刘树柏
Owner SHAOXING RUIKANG BIOTECHNOLOGES CO INC
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