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Preparation method of hexafunctional epoxy resin based on cyclotriphosphazene

A six-functional, epoxy resin technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve the problems of poor comprehensive performance of flame retardant systems, and achieve flame retardant performance. Excellent, the effect of improving mechanical properties and heat resistance

Active Publication Date: 2019-10-18
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In order to overcome the shortcomings of the poor comprehensive performance of the epoxy resin flame retardant system prepared by the existing method, the present invention provides a method for preparing a hexafunctional epoxy resin based on cyclotriphosphazene

Method used

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  • Preparation method of hexafunctional epoxy resin based on cyclotriphosphazene
  • Preparation method of hexafunctional epoxy resin based on cyclotriphosphazene
  • Preparation method of hexafunctional epoxy resin based on cyclotriphosphazene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Step 1. Dissolve 51.7g of potassium carbonate and 10g of hexachlorocyclotriphosphazene (HCCP) in 150mL of tetrahydrofuran, weigh 24.6g of p-hydroxybenzaldehyde (PHB) and dissolve in 100mL of tetrahydrofuran, and slowly add it dropwise to the above system in an ice bath After the dropwise addition was completed, the ice bath was removed, and the reaction was performed at room temperature for 0.5h, and then moved to an oil bath to reflux for 48h. The filtrate was concentrated, extracted with chloroform, washed with saturated sodium chloride, and dried over anhydrous sodium sulfate. Filter and remove the solvent under reduced pressure to obtain a crude product. Recrystallize with dichloromethane and dry in vacuo to obtain 22.7g of white crystalline solid, i.e. hexa(4-formylphenoxy)cyclotriphosphazene (HAPCP), structural formula:

[0029]

[0030] The yield was 89%.

[0031] NMR 1 H NMR (400MHz, CDCl 3 )δ9.94 (s, 1H), 7.74 (d, 2H), 7.15 (d, 2H). 31 P NMR (162MHz, CD...

Embodiment 2

[0061] Step 1. Under the protection of ice bath and inert gas, 24.6g of PHB and 20.4g of triethylamine (TEA) were added to 150mL of tetrahydrofuran, and HCCP (10g) dissolved in 50mL of tetrahydrofuran was added dropwise. After the dropwise addition, the reaction system was moved into an oil bath, heated to reflux, and reacted for 24 hours. After the reaction was finished, the hydrochloride of triethylamine was removed by suction filtration, and after the solvent was removed by rotary evaporation, 200mL of water was added to precipitate the crude product. Finally, it was recrystallized with ethyl acetate and vacuum-dried to obtain 22.8g of pure HAPCP. The yield was 92%, the structural formula is:

[0062]

[0063] NMR 1 H NMR (400MHz, CDCl 3 )δ9.94 (s, 1H), 7.74 (d, 2H), 7.15 (d, 2H). 31 P NMR (162MHz, CDCl 3 ) δ7.3.

[0064] Step 2. Under ice-bath conditions, add 8.1g of potassium borohydride in batches to HAPCP (20g) dissolved in 100mL of methanol and tetrahydrofuran ...

Embodiment 3

[0076] Step 1. Add 121.8g of cesium carbonate and 10g of hexachlorocyclotriphosphazene into 150mL of tetrahydrofuran, weigh 24.6g of p-hydroxybenzaldehyde and dissolve it in 100mL of tetrahydrofuran, and slowly drop it into the above reaction system under ice bath conditions, and the dropwise addition is completed Finally, the ice bath was removed, and the reaction was carried out at room temperature for 0.5 h, and then stirred at reflux for 48 h. Filtrate with suction, concentrate the filtrate, extract with chloroform, wash with saturated sodium chloride, and dry over anhydrous sodium sulfate. Filter and remove the solvent under reduced pressure to obtain a crude product. Recrystallized from dichloromethane and dried under vacuum to obtain 23.3 g of HAPCP with a yield of 94%. The structural formula is:

[0077]

[0078] Step 2. 20 g of HAPCP was dissolved in 100 mL of tetrahydrofuran and methanol mixed solvent, and 5.7 g of sodium borohydride was added in batches under i...

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Abstract

The invention discloses a preparation method of six-functionality epoxy resin based on cyclotriphosphazene, which aims at solving the technical problem of poor comprehensive property in the existing prepared epoxy resin flame-retardant system. The preparation method adopts the technical scheme with the following steps of firstly, performing nucleophilic substitution on p-hydroxybenzaldehyde and phosphonitrilic chloride trimer under the condition of alkaline existence, so as to obtain a hexaaldehyde compound HAPCP; using sodium borohydride or lithium borohydride to reduce the HAPCP, so as to obtain a hexahydroxy intermediate HHPCP; dissolving the HHPCP, bromopropylene and alkaline into an organic solvent, so as to obtain HAMPCP; oxidizing a hexaalkenyl-containing compound HAMPCM by metachloroperbenzoic acid in an organic solvent, so as to obtain a hexaepoxy target product HGPCP. The preparation method has the advantages that because the molecular structure of HGPCP contains six epoxy functional groups, the mechanical property and heat-resistant property are improved; by containing the cyclotriphosphazene structure with the flame-retardant property, the flame-retardant property is very excellent, the limited oxygen index is greater than 30%, and the UL-94 reaches V-0 level.

Description

technical field [0001] The invention relates to a preparation method of epoxy resin, in particular to a preparation method of cyclotriphosphazene-based hexafunctional epoxy resin. Background technique [0002] Epoxy resin generally refers to organic compounds such as aliphatic, alicyclic or aromatic as the skeleton, and contains two or more epoxy groups in the molecular structure. Under appropriate conditions, the epoxy group reacts with the curing agent. to form useful thermoset products. The cured epoxy resin has the characteristics of high mechanical properties, good thermal stability, low shrinkage, outstanding electrical insulation, high bonding strength, and excellent chemical corrosion resistance, so it is widely used as adhesives, coatings, and resin substrates Used in various fields of national defense and national economy such as electronic appliances, aerospace, etc. [0003] In addition to common bifunctional epoxy resins, multifunctional epoxy resins contain m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/659C08G59/32
Inventor 张广成周立生史学涛李建伟李建通张鸿鸣冯云杰
Owner NORTHWESTERN POLYTECHNICAL UNIV
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