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Phosphorus-nitrogen containing halogen-free flame-retardant hyperbranched epoxy resin and preparation method thereof

An epoxy resin, flame retardant technology, which is applied in the field of phosphorus-nitrogen-free halogen-free flame retardant hyperbranched epoxy resin and its preparation, can solve the problem of no flame retardant function and the like, and achieve good catalytic activity and selectivity , The effect of low raw material cost and low thermal stability

Active Publication Date: 2017-06-13
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently reported hyperbranched epoxy resins have obvious strengthening and toughening effects on epoxy resins, but they do not have a flame retardant function. Important development direction of epoxy resin preparation and application

Method used

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  • Phosphorus-nitrogen containing halogen-free flame-retardant hyperbranched epoxy resin and preparation method thereof
  • Phosphorus-nitrogen containing halogen-free flame-retardant hyperbranched epoxy resin and preparation method thereof
  • Phosphorus-nitrogen containing halogen-free flame-retardant hyperbranched epoxy resin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Mix 216g of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide DOPO, 112g of itaconic anhydride ITA and 184g of toluene, stir and react at 120°C for 4h, filter after the reaction, 60 ℃ vacuum drying for 12h to obtain DOPO-ITA. 164.0g DOPO-ITA, 66.5g diisopropanolamine DIPA, 22.3g trimethylolpropane, 0.32g 1-butylsulfonic acid-3-methylimidazolium bisulfate ([BHSO 3 MIM]HSO 4 ) and 0.32g of 1-ethyl-3-methylimidazolium bisulfate (EMIMHSO 4 ) at 180° C., heated and mixed evenly, and stirred for 1 h to obtain the first-generation hydroxyl-terminated hyperbranched polyester amide HBPP-1. 73.2g HBPP-1, 35.0g mercaptopropionic acid, 46.0g toluene and 0.9g p-toluenesulfonic acid were reacted at 80°C for 10h. After the reaction, the toluene and excess mercaptopropionic acid were removed under reduced pressure to obtain the mercapto-terminated hyperbranched polymer TBPP- 1. Mix 40.7g TBPP-1, 17.1g allyl glycidyl ether AGE and 0.1g 1-hydroxycyclohexyl phenyl ketone evenly, stir...

Embodiment 2

[0033] Mix 216.0g of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide DOPO, 112.0g of itaconic anhydride ITA, 106.0g of xylene and 72.0g of tetrahydrofuran, and stir the reaction at 100°C After 6 hours of reaction, filter and dry at 60° C. for 12 hours to obtain 263.9 g of DOPO-ITA. 164.0g DOPO-ITA, 66.5g diisopropanolamine DIPA, 7.4g trimethylolpropane, 0.35g 1-butylsulfonic acid-3-methylimidazolium bisulfate ([BHSO 3 MIM]HSO 4 ) and 0.35g of 1-ethyl-3-methylimidazolium bisulfate (EMIMHSO 4) at 170° C., heated and mixed evenly, and stirred for 2 hours to obtain the second-generation hydroxyl-terminated hyperbranched polyester amide HBPP-2. 82.4g of HBPP-2, 27.9g of mercaptopropionic acid, 44.2g of toluene and 1.0g of p-toluenesulfonic acid were reacted at 100°C for 9 hours. After the reaction, the toluene and mercaptopropionic acid were removed under reduced pressure to obtain TBPP-2, a mercapto-terminated hyperbranched polymer. Mix 45.5g TBPP-2, 20.6g AGE and 0.2g 2,4,6...

Embodiment 3

[0035] Mix 216.0g of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide DOPO, 112.0g of itaconic anhydride ITA and 212.0g of xylene, stir and react at 80°C for 8h, and the reaction ends Then filter and dry to obtain 266.5g DOPO-ITA. 164.0g DOPO-ITA, 66.5g diisopropanolamine DIPA, 3.2g trimethylolpropane, 0.45g 1-butylsulfonic acid-3-methylimidazolium bisulfate ([BHSO 3 MIM]HSO 4 ) and 0.45g 1-ethyl-3-methylimidazolium bisulfate (EMIMHSO 4 ) at 160° C., heated and mixed evenly, and stirred for 3 hours to obtain the third-generation hydroxyl-terminated hyperbranched polyester amide HBPP-3. 94.4g of HBPP-3, 27.9g of mercaptopropionic acid, 92.0g of toluene and 1.1g of p-toluenesulfonic acid were reacted at 90°C for 8 hours. After the reaction, the toluene and mercaptopropionic acid were removed under reduced pressure to obtain TBPP-3, a mercapto-terminated hyperbranched polymer. Mix 103.0g TBPP-3, 41.1g allyl glycidyl ether AGE and 0.5g 2-methyl-1-[4-methylthiophenyl]-2-morpho...

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Abstract

The invention discloses a phosphorus-nitrogen containing halogen-free flame-retardant hyperbranched epoxy resin and a preparation method thereof. The preparation method for the phosphorus-nitrogen containing halogen-free flame-retardant hyperbranched epoxy resin comprises the steps: firstly, enabling 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, itaconic anhydride, polyol amine and trimethylolpropane to react with one another under an effect of an acidic ionic liquid catalyst to obtain hydroxyl-terminated hyperbranched polyester-amide; and enabling hydroxyl-terminated hyperbranched polyester-amide to react with mercaptoacetic acid or mercaptopropionic acid and allyl glycidyl ether in sequence to obtain the phosphorus-nitrogen containing halogen-free flame-retardant hyperbranched epoxy resin. The phosphorus-nitrogen containing halogen-free flame-retardant hyperbranched epoxy resin and the preparation method thereof, disclosed by the invention, have the advantages of simple process, narrow intermediate product molecular weight distribution, higher purity, good enhancing, toughening and flame retardant functions of the final product and wide application prospect.

Description

technical field [0001] The invention relates to the field of high-performance polymer resins, in particular to a phosphorus-nitrogen-containing halogen-free flame-retardant hyperbranched epoxy resin and a preparation method thereof. Background technique [0002] The structure of the hyperbranched epoxy resin mainly includes the core part of the hyperbranched structure and the end group part with epoxy functional groups. The performance of hyperbranched epoxy resin is determined by its molecular structure. The cavity structure inside the molecule can chelate ions, adsorb small molecules, or serve as catalytic active sites for chemical reactions. Due to the highly branched structure of hyperbranched epoxy resin, it is difficult to crystallize, no chain entanglement, low viscosity and high solubility, and a large number of epoxy groups on the periphery of the molecule have the unique properties of epoxy resin. These factors It has a wide range of applications in many fields. ...

Claims

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Application Information

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IPC IPC(8): C08G59/02C08G59/30C08G69/44C08G69/48C08L63/00
CPCC08G59/027C08G69/44C08G69/48C08L63/00C08L2203/20
Inventor 张俊珩陈诗媛张道洪张爱清
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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