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Phosphor series benzoxazine and preparation method

A technology of benzocyclohexane and oxo, which is applied in the field of phosphorus-based oxonitrobenzocyclohexane and its preparation, can solve the problems of being complicated, inconvenient to operate, unsuitable for large-scale production and the like, and achieve the synthesis steps Simple, easy to process, improve the effect of poor flame resistance

Active Publication Date: 2012-11-28
高鼎精细化工(昆山)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these two synthetic routes are relatively complicated, inconvenient to operate, and not suitable for large-scale production.

Method used

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  • Phosphor series benzoxazine and preparation method
  • Phosphor series benzoxazine and preparation method
  • Phosphor series benzoxazine and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1.5, the synthesis of 5'-methylene-bis-2-hydroxybenzaldehyde

[0029] 5,5'-methylene-bis-2-hydroxybenzaldehyde is obtained by reacting 2-hydroxybenzaldehyde with trioxane, and its chemical reaction formula is:

[0030]

[0031] Its synthetic steps are as follows:

[0032] In a 0.25L three-neck reactor with a temperature indicating device, add 10g (0.111mol) of trioxane, 89.5g (0.733mol) of 2-hydroxybenzaldehyde, 100g of acetic acid and 3.09g of sulfuric acid React at 85°C for 24 hours. After the reaction, let cool and precipitate naturally. Dissolve the precipitate in methanol and pour it directly into 1000mL deionized water for precipitation and washing, and filter it with a suction filter. The filter cake was dried in a vacuum oven at 110° C. to obtain the product, and the yield was 40%.

[0033] The molecular formula of this product is C 15 h 12 o 4 , the high resolution mass spectrometer identified its molecular weight as 256.2534. Its NMR as fi...

Embodiment 27

[0034] Example 2.7,7'-methylene-bis-[2-dihydro-3-phenyl-4-(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) Synthesis of -4-Hydroxy-1,3-Oxoazinobenzocyclohexane] (Bz-a)

[0035] Bz-a is obtained by reacting DOPO, 5,5'-methylene-bis-2-hydroxybenzaldehyde, aniline and formaldehyde, and its chemical reaction formula is:

[0036]

[0037] The synthesis steps are as follows: In a 0.25L three-neck reactor with a temperature indicating device, add 12.81g (0.05mol) of 5,5'-methylene-bis-2-hydroxybenzaldehyde, 9.3g (0.1 mol) of aniline, 100mL of methanol and 21.6g (0.1mol) of DOPO were reacted at room temperature (25°C) for 18 hours, white powder precipitated during the reaction, and 8.9g (0.11mol) was added immediately after the reaction with a volume fraction of 37% Formaldehyde aqueous solution, first react at room temperature (25°C) for 4 hours, then raise the reaction temperature to reflux temperature, react at reflux temperature for 12 hours, after cooling down to room tem...

Embodiment 37

[0038] Example 3.7,7'-methylene-bis-[2-dihydro-3-n-propyl-4-(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide )-4-Hydroxy-1,3-oxoazinobenzocyclohexane] (Bz-b)

[0039] Bz-b is obtained by reacting DOPO, 5,5'-methylene-bis-2-hydroxybenzaldehyde, propylamine and formaldehyde, and its chemical reaction formula is:

[0040]

[0041] The synthesis steps are as follows: In a 0.25L three-neck reactor with a temperature indicating device, add 12.81g (0.05mol) of 5,5'-methylene-bis-2-hydroxybenzaldehyde, 5.91g (0.1 mol) of propylamine, 100mL of methanol and 21.6g (0.1mol) of DOPO were reacted at room temperature (25°C) for 18 hours. During the reaction, a yellow powder was precipitated. Immediately after the reaction, 8.93g (0.11mol) was added with a volume fraction of 37%. Formaldehyde aqueous solution, first react at room temperature (25°C) for 4 hours, then raise the reaction temperature to reflux temperature, react at reflux temperature for 12 hours, after returning to room t...

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Abstract

The invention discloses phosphor series benzoxazine and a preparation method, which is characterized in that 2-hydroxybenzaldehyde and trioxane react to synthesize 5,5'-methylene-bis-2-hydroxybenzaldehyde, then 5,5'-methylene-bis-2-hydroxybenzaldehyde, DOPO (9,10-dihydro-9-oxa-10-phospha phenanthrene-10-oxide), formaldehyde and monofunctional amine are reacted to generate the phosphor series benzoxazine. According to the invention, the synthesis step is simple, DOPO can be directly used to reduce C=N double bond during the synthesis process, after the reaction is completed, a dead cycle is carried out by adding formaldehyde without precipitation, and the synthesis method has the advantages of convenient processing and mass production. When the phosphor series benzoxazine is taken as a hardener and reacted with epoxy resin, the cured epoxy resins with excellent thermal property, thermostability and fire retardant property can be formed.

Description

technical field [0001] The invention relates to a phosphorus-based oxoazinobenzocyclohexane and a preparation method thereof, in particular to a phosphorus-based oxoazinobenzocyclohexane used as an epoxy resin hardener and a preparation method thereof. Background technique [0002] Oxoazinobenzocyclohexane resin is a kind of phenolic resin, which is characterized in that the monomer will be ring-opened and hardened after heating, but it will not release water when hardened, so it has better processability than phenolic resin. However, since oxoazinobenzocyclohexane resin does not have flame retardant properties, it is often necessary to add additional flame retardants to give it more industrial application value. [0003] In recent years, organophosphorus compounds have been studied to improve the flame retardant properties of polymers. Compared with traditional additive flame retardants, reactive organophosphorus compounds will not reduce the mechanical properties of cured ...

Claims

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Application Information

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IPC IPC(8): C07F9/6574C08G59/40
Inventor 林棋灿
Owner 高鼎精细化工(昆山)有限公司
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