Preparation method for polymerization-type asymmetric hindered phenol anti-oxidant resins

A technology of asymmetric hindered phenol and antioxidant, which is applied in the field of preparing polymerized asymmetric hindered phenol antioxidant resin

Inactive Publication Date: 2013-12-04
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently disclosed phenolic antioxidant literature, such as: CN 100424122C discloses a p-cresol-dicyclopentadiene styrenated antioxidant, which polymerizes with styrene at the ortho position of the phenolic hydroxyl group, and only one A larger ortho group, low antioxidant efficiency
CN101402721A discloses a synthesis method of p-cresol-dicyclopentadiene isobutynylated antioxidant resin. Concentrated sulfuric acid catalyst is used in the production of this process, which is highly corrosive, and a large amount of solid waste will be generated by using activated clay to remove the catalyst and decolorize , increasing the pollution of the environment
CN101967223A discloses a synthesis method of methylphenol-dicyclopentadiene isobutyl resin antioxidant. The process uses composite sulfonic acid as a butylation catalyst, and p-cresol, dicyclopentadiene and isobutylene are synthesized as raw materials Methylphenol-dicyclopentadiene isobutyl resin antioxidant, because the ortho position of the antioxidant space structure has only tert-butyl group, the antioxidant effect is low; the raw material is isobutylene, which is not suitable for storage and has potential safety hazards

Method used

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  • Preparation method for polymerization-type asymmetric hindered phenol anti-oxidant resins
  • Preparation method for polymerization-type asymmetric hindered phenol anti-oxidant resins

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a 500ml reactor equipped with a stirrer, reflux condenser, feeding device and nitrogen protection device, add 400g toluene, 100g o-tert-butyl-p-cresol, 10g strong acid resin catalyst, replace with nitrogen, and heat to 83°C 120g of dicyclopentadiene was added dropwise with a pump, and the dropwise addition time was 30min. After the dropwise addition, the temperature was raised to 113°C. After 3.5h of reaction, 1.5g of phosphoric acid, 9g of alkylation catalyst were added, and the reaction temperature was 85°C, and methanol was added dropwise 30g, dripping time 60min, react for 120min after the completion of the dropwise addition, remove the resin catalyst by filtration after the reaction, wash with alkali and water until neutral, remove oligomers by steam stripping, and distill under reduced pressure after the solvent and unreacted raw materials, distill After cooling to 206° C., 136 g of the product was obtained, and the calculated product yield was 79.2%. The produ...

Embodiment 2

[0021] In a 500ml reactor equipped with a stirrer, reflux condenser, feeding device and nitrogen protection device, add 400g toluene, 100g o-tert-butyl-p-cresol, 20g strong acid resin catalyst, replace with nitrogen, and heat to 90°C 160g of dicyclopentadiene was added dropwise with a pump, and the dropwise addition time was 80min. After the dropwise addition, the temperature was raised to 120°C. After 4h of reaction, 2g of phosphoric acid, 13.5g of alkylation catalyst were added, and the reaction temperature was 78°C, and 35g of methanol was added dropwise. , the dropwise addition time is 45min, after the dropwise addition, react for 100min, remove the resin catalyst by filtration after the reaction, wash with alkali and water to neutrality, remove oligomers by steam stripping, and distill under reduced pressure after the solvent and unreacted raw materials, and distill to 152 g of the product was obtained after cooling at 239° C., and the calculated product yield was 82.4%. ...

Embodiment 3

[0023] In a 500ml reactor equipped with a stirrer, reflux condenser, feeding device and nitrogen protection device, add 600g toluene, 100g o-tert-butyl-p-cresol, 12g strong acid resin catalyst, replace with nitrogen, and heat to 95°C , Add 150g of dicyclopentadiene dropwise with a pump, and the dropping time is 90min. After the dropwise addition, the temperature is raised to 115°C. After 4.5h of reaction, 1.6g of phosphoric acid and 12g of alkylation catalyst are added. The reaction temperature is 80°C, and methanol is added dropwise. And ethanol molar ratio 1: 1 raw material 40g, dropwise time 40min, react 120min after dropwise, filter to remove resin catalyst after reaction, alkali wash and water wash to neutrality, water vapor stripping removes oligomer, solvent and untreated The reaction raw materials were then distilled under reduced pressure to 237° C., and 156 g of the product was obtained after cooling, and the product yield was calculated to be 83.5%. The product is a...

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Abstract

Provided is a preparation method for polymerization-type asymmetric hindered phenol anti-oxidant resins. The preparation method comprises steps: with strong acid resins as catalysts, and benzene or cyclohexane as a solvent, 2-tert-Butyl-p-cresol and dicyclopentadiene are subjected to a polymerization reaction to form phenol-type petroleum resins; the phenol-type petroleum resins and saturated alcohols with one to three carbons are subjected to an alkylation reaction to form polymerization-type asymmetric hindered phenol anti-oxidant resins in presence of phosphoric acid and nickel-containing catalysts; the alkylation reaction products are subjected to reduced pressure distillation to remove the unreacted raw materials and solvent to obtain polymerization-type asymmetric hindered phenol antioxidant resin products. The preparation method has obvious positive effects, the polymerization reaction and the alkylation reaction have high selectivity and conversion rate, and the yield is about 80%. What is more important is that compared to traditional hindered phenol antioxidants, the synthesized polymerization-type asymmetric hindered phenol antioxidant resins are advantaged by high antioxidant activity, high heat stability, extracting resistance, compatibility, non-toxic and environmentally friendly characteristics.

Description

technical field [0001] The present invention relates to a method for preparing a polymeric asymmetric hindered phenolic antioxidant resin, in particular to preparing a polymeric asymmetric hindered phenolic antioxidant resin from dicyclopentadiene, o-tert-butyl p-cresol and C1-C3 saturated alcohol through polymerization and alkylation. Asymmetric hindered phenolic antioxidant resin approach. Background technique [0002] Antioxidants are a class of polymer additives that can effectively reduce the rate of autoxidation of plastic or rubber products and delay aging degradation, and their applications involve almost all polymer products. Since most polymers need to be heated at 220-350°C to be processed into products, traditional antioxidants are easy to volatilize at high temperatures, thus affecting the performance of products and causing environmental degradation. At present, the typical antioxidants are amines and phenols. Among them, amine antioxidants are mainly used in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/17C07C37/16
CPCY02P20/52
Inventor 刘威廉孙春水黄勇周秀风吴卓
Owner CHINA PETROLEUM & CHEM CORP
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