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A kind of phosphorus-containing benzoxazine monomer and preparation method thereof

A technology of benzoxazine and monomer, applied in the field of phosphorus-containing benzoxazine monomer and preparation thereof, can solve the problems of high curing temperature, not easy and simple monomer synthesis, environmental protection, insufficient material performance, etc. Excellent comprehensive performance, strong industrial value and practical application value, excellent flame retardant performance

Active Publication Date: 2020-01-24
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, although the flame retardancy of the benzoxazine obtained in the above patents has been improved to a certain extent, other properties such as monomer synthesis are not simple enough, environmental protection, high curing temperature and the performance of the cured material are not excellent enough.

Method used

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  • A kind of phosphorus-containing benzoxazine monomer and preparation method thereof
  • A kind of phosphorus-containing benzoxazine monomer and preparation method thereof
  • A kind of phosphorus-containing benzoxazine monomer and preparation method thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0041] The preparation method of the aforementioned phosphorus-containing benzoxazine resin, in step 1, DOPO-HQ, amine compounds, and paraformaldehyde are mixed in proportion, added to the flask, and the low-polarity solvent is used as the reaction solvent. Stir and react in an oil bath, slowly increase the temperature from room temperature to 110-130° C., and react for 12-24 hours to obtain a hydroxyl-functionalized phosphorus-containing benzoxazine intermediate.

[0042] The preparation method of the aforementioned phosphorus-containing benzoxazine resin, in the second step, the hydroxyl functionalized phosphorus-containing benzoxazine intermediate is mixed in proportion with 3-bromo-propyne and anhydrous potassium carbonate , with DMF as solvent, react at 0-120°C for 1-24h.

[0043] get the product.

Embodiment 1

[0045] Mix 2g DOPO-HQ, 0.572g aniline, and 0.406g (10% excess) paraformaldehyde in proportion, add them to the flask, use xylene as the reaction solvent, stir in the oil bath, and the temperature rises slowly from room temperature to 120°C , and reacted for 12h to obtain a hydroxyl-functionalized phosphorus-containing benzoxazine intermediate.

[0046] Get 1.5g of the obtained hydroxyl-functionalized phosphorus-containing benzoxazine intermediate with 0.484g 3-bromo-propyne (20% in excess), 0.672g of anhydrous potassium carbonate (50% in excess), and get 30mlDMF as a solvent at 80 Reaction at ℃ for 24h.

[0047] The solution obtained by the reaction was washed three times with 5% NaOH solution, then washed three times with water, and dried in a vacuum oven for one day.

[0048] Get the product:

[0049] The infrared spectrum and differential scanning calorimetry characterization results of this product are shown in the appendix figure 1 And attached figure 2 . attached...

Embodiment 2

[0051] Mix 2g DOPO-HQ, 0.557g aniline, and 0.395g (7% excess) paraformaldehyde in proportion, add them to the flask, use xylene as the reaction solvent, stir in the oil bath, and the temperature rises slowly from room temperature to 100°C , and reacted for 24h to obtain a hydroxyl-functionalized phosphorous-containing benzoxazine intermediate.

[0052] 1 g of the obtained hydroxyl-functionalized phosphorus-containing benzoxazine intermediate was mixed with 0.310 g of 3-bromo-propyne, 0.419 g of anhydrous potassium carbonate, and 20 ml of DMF as a solvent, and reacted at 80° C. for 12 h.

[0053] The solution obtained by the reaction was washed three times with 5% NaOH solution, then washed three times with water, and dried in a vacuum oven for one day.

[0054] Get the product:

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Abstract

The invention belongs to the field of resin materials and provides a phosphorus-containing benzoxazine monomer and a preparation method thereof. The preparation method comprises the steps: firstly, putting 10-(2,5-dyhydroxy phenyl)-10-hydrogen-9-oxa-10-phosphaphenanthrene-10-oxide DOPO-HQ, amine compound and paraformaldehyde into a low-polar solvent according to a proportion to react to obtain hydroxyl functionalization phosphorus containing benzoxazine intermediate; then, putting the hydroxyl functionalization phosphorus containing benzoxazine intermediate, brominated compound Br-R2 and potassium carbonate into a strong-polar solvent; after reaction is finished, alkali washing and water washing reaction fluid to remove the solvent and drying to obtain a target product. According to the phosphorus containing benzoxazine monomer disclosed by the invention, phosphorus is guided into benzoxazine molecules, so that heat resistance and flame retardance of benzoxazine resin are obviously improved, and a flame-retardant coefficient of the benzoxazine resin can reach UL94V-0 level; meanwhile, the phosphorus containing benzoxazine monomer has the advantage of simple preparation technology,resin with excellent comprehensive performance can be prepared out by changing R1 and R2 radicals, and the phosphorus containing benzoxazine monomer is suitable for preparing high-performance compoundmaterials.

Description

technical field [0001] The invention relates to a thermosetting resin and a preparation method thereof, in particular to a phosphorus-containing benzoxazine monomer and a preparation method thereof. Background technique [0002] Polybenzoxazines are useful in various fields such as electronic packaging materials, materials for aerospace and other transportation applications, and ballistics. Since the benzoxazine reaction does not produce by-products, it has very good development potential from the perspective of environmental protection. Volume shrinkage close to zero is also a great advantage. Benzoxazine has flexible molecular design, and can synthesize benzoxazine monomers with different structures by selecting different types of phenolic and amine compounds according to performance requirements. At the same time, the existing benzoxazines also have some shortcomings, such as high curing temperature, and the heat resistance still needs to be further improved before they...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6568C08G14/06
CPCC07F9/65685C08G14/06
Inventor 张侃张关胜刘宇奇曾凤
Owner JIANGSU UNIV