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 preparation of polymerized asymmetric hindered phenolic antioxidant resin, and can solve the problems of synthesis process pollution, antioxidant activity and thermal stability of antioxidants, etc.

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

The technical problem to be solved is that the existing antioxidant has poor antioxidant activity and thermal stability, and the defects of serious pollution in the synthesis process

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

[0018] In the 500ml reactor equipped with stirrer, reflux condenser, feeding device and nitrogen protection device, add 100g toluene, 100g p-cresol, 2g boron trifluoride complex catalyst, after replacing with nitrogen, heat to 85 ℃, add 80g of dicyclopentadiene dropwise with a pump, and the dropping time is 60min. After the dropwise addition, the temperature is raised to 132°C. After reacting for 3h, the reaction solution is washed with alkali and washed with water, and the unreacted p-methyl group is distilled off under reduced pressure. Phenol, then add 100g of solvent toluene, 1.5g of phosphoric acid, 10g of alkylation catalyst, reaction temperature 76°C, dropwise add 20g of methanol and isobutanol molar ratio 3:7 mixed raw materials, dropwise time 20min, after dropwise addition, react After 2 hours, after alkali washing and water washing, the solvent and unreacted raw materials were distilled off under reduced pressure, distilled to 216° C., and 146 g of the product was obt...

Embodiment 2

[0020] In the 500ml reactor equipped with stirrer, reflux condenser, feeding device and nitrogen protection device, add 100g toluene, 100g p-cresol, 3g boron trifluoride complex catalyst, after replacing with nitrogen, heat to 90 ℃, use a pump to add 120g of dicyclopentadiene dropwise for 30 minutes, after the dropwise addition, raise the temperature to 140°C, and react for 3 hours, the reaction solution is washed with alkali, and after washing with water, the unreacted p-methyl group is distilled off under reduced pressure. Phenol, add 100g of solvent toluene, 1.5g of phosphoric acid, 12g of alkylation catalyst, reaction temperature 80 ℃, dropwise add methanol and isobutanol molar ratio 5: 5 mixed raw materials, dropwise time 22min, react after dropwise After 2 hours, after alkali washing and water washing, the solvent and unreacted raw materials were distilled off under reduced pressure, distilled to 262° C., and 182 g of the product was obtained after cooling. The calculated...

Embodiment 3

[0022] In the 500ml reactor equipped with stirrer, reflux condenser, feeding device and nitrogen protection device, add 100g toluene, 100g p-cresol, 2g boron trifluoride complex catalyst, after replacing with nitrogen, heat to 83 ℃, use a pump to add 100g of dicyclopentadiene dropwise, and the dropping time is 60min. After the dropwise addition, the temperature is raised to 125°C. After 3 hours of reaction, the reaction solution is washed with alkali, and after washing with water, the unreacted p-methyl group is distilled off under reduced pressure. Phenol, then add 100g of solvent toluene, 1.5g of phosphoric acid, 10g of alkylation catalyst, reaction temperature 80°C, dropwise add 20g of ethanol and isobutanol molar ratio 3:7 mixed raw materials, dropwise time 20min, after dropwise addition, react After 2.5 hours, after alkali washing and water washing, the solvent and unreacted raw materials were distilled off under reduced pressure, distilled to 231° C., and 172 g of the pro...

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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 boron trifluoride complex as a catalyst and benzene or cyclohexane as a solvent, p-methylphenol and dicyclopentadiene are subjected to a polymerization reaction to form phenol-type petroleum resins; after alkali washing and water washing, the polymerization reaction products are subjected to reduced pressure distillation to remove unreacted p-methylphenol in the reaction liquid to obtain refined phenol-type petroleum resins; the phenol-type petroleum resins, saturated alcohols with one to three carbons and isobutanol are subjected to an alkylation reaction to form polymerization-type asymmetric hindered phenol anti-oxidant resins in a solvent 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, and the yield is about 90%. The preparation method has obvious positive effects, through asymmetric substituent groups antioxidant effects are raised. Compared to traditional 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 invention relates to a preparation method of a polymeric asymmetric hindered phenolic antioxidant resin, in particular to dicyclopentadiene, p-cresol, C1-C3 saturated alcohol and isobutanol through polymerization and alkylation reaction A method for preparing polymeric asymmetric hindered phenolic antioxidant resin. 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 rubber due to their high toxicity, and they are ea...

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 刘威廉谢家明黄勇陆徐国华建英
Owner CHINA PETROLEUM & CHEM CORP
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