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Benzoxazine-derived phosphorus bisphenol, epoxy resin semi-cured substance and epoxy resin cured substance thereof, and manufacturing method their manufacturing method

A technology of epoxy resin and semi-cured product, applied in the field of phosphorus-based bisphenol compounds, can solve problems such as inconvenience, general products and methods do not have suitable structures and methods, etc.

Inactive Publication Date: 2012-07-11
萧介夫
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] It can be seen that the above-mentioned existing phosphorus-based bisphenol compounds, their derivatives and manufacturing methods obviously still have inconvenience and defects in product structure, manufacturing method and use, and need to be further improved urgently.
In order to solve the above-mentioned problems, the relevant manufacturers have tried their best to find a solution, but no suitable design has been developed for a long time, and there is no suitable structure and method for general products and methods to solve the above-mentioned problems. This is obviously a problem that relevant industry players are eager to solve

Method used

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  • Benzoxazine-derived phosphorus bisphenol, epoxy resin semi-cured substance and epoxy resin cured substance thereof, and manufacturing method their manufacturing method
  • Benzoxazine-derived phosphorus bisphenol, epoxy resin semi-cured substance and epoxy resin cured substance thereof, and manufacturing method their manufacturing method
  • Benzoxazine-derived phosphorus bisphenol, epoxy resin semi-cured substance and epoxy resin cured substance thereof, and manufacturing method their manufacturing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0125] Synthesis of phosphorus bisphenol compound (I):

[0126] According to the embodiment of the present invention, the phosphorus-based bisphenol compound (I) can be synthesized by mixing DOPO and benzoxazine monomer (A) in a solvent and heating, and the reaction formula is as follows:

[0127]

[0128] Among them, R 1 is selected from the following groups:

[0129] H, -C n h 2n+1 ,-O-C n h 2n+1 , -CN

[0130]

[0131] -F, -Cl, -Br, -I

[0132] -CF 3 ,-O-CF 3 ,-NO 2 , -B(OH) 2

[0133] X contains the structures shown below:

[0134]

[0135] Wherein, n is an integer and 1≤n≤10.

[0136] Phosphorus-based bisphenol compound (I) derived flame retardant phosphorus-based epoxy resin semi-cured product (III):

[0137] The phosphorus-based bisphenol compound (I) can further carry out a chain extension reaction with a compound having an epoxy group structure to synthesize a flame-retardant phosphorus-based epoxy resin semi-cured product (III). The compou...

Embodiment approach 2

[0150] Phosphorous bisphenol compound (II):

[0151] According to this embodiment, the phosphorus-based bisphenol compound (II) is synthesized by mixing and heating benzoxazine monomer (B) and DOPO in a solvent. The reaction formula is as follows:

[0152]

[0153] Among them, R 2 is selected from the following groups:

[0154]

[0155] X can include but not limited to the structures shown below:

[0156]

[0157] Wherein, n is an integer of 1≤n≤10.

[0158] Synthesis of flame-retardant phosphorus-based epoxy resin semi-cured product (IV) with phosphorus-based bisphenol compound (II):

[0159] Phosphorous bisphenol compound (II) can use the same method as Embodiment 1 to carry out chain extension reaction with the compound (C) having an epoxy group structure at 100-200°C to synthesize a flame-retardant phosphorus-based epoxy resin semi-cured Object (IV), the reaction is as follows:

[0160]

[0161] Wherein, m is a number of 1≤m≤10, and Y is selected from the ...

Synthetic example 1-1

[0167] Preparation of Phosphorous Bisphenol Compound (I-a)

[0168] According to the structure of the phosphorus-based bisphenol compound (I), X can be synthesized as CH The phosphorus-based bisphenol compound (I-a) has the following structure:

[0169]

[0170] The synthetic method of phosphorus-based bisphenol compound (I-a) is to get 0.2 moles (86.9 grams) of benzoxazine resin P-d (commercialized benzoxazine resin P-d) derived from aromatic diamine 4,4'-diaminodiphenylmethan (DDM). P-d, available from Shikoku Chemicals Corporation) and 0.4 moles (86.46 g) of DOPO were charged into a 500 mL single-port round bottom reactor containing 200 mL of Tetrahydrofuran (THF). After reacting at room temperature for 1 hour and completely dissolving, the temperature was raised to reflux temperature, and the reaction was continued for 12 hours. After the reaction is over, pour it directly into 1000 ml of deionized water for precipitation and washing, and filter it with a suction filte...

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Abstract

The invention relates to a benzoxazine-derived phosphorus bisphenol, an epoxy resin semi-cured substance and an epoxy resin cured substance thereof, and a manufacturing method thereof. The method comprises the following steps: reacting 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and benzoxazine derivatives to generate the phosphorus bisphenol compound; and further reacting the phosphorus bisphenol compound and epoxy resin to obtain the flame-resisting phosphorus epoxy resin semi-cured substance and epoxy resin cured substance.

Description

technical field [0001] The invention relates to a phosphorus-based bisphenol compound, its derivatives and a production method, in particular to a phosphorus-based bisphenol compound derived from benzoxazine and a production method thereof. Background technique [0002] At present, in epoxy resins for printed circuit boards, halogens and antimony trioxide are the main flame-resistant additives. For example, propanediol tetrabromide containing halogens is a commonly used flame-resistant agent for epoxy resins. [0003] However, the cured epoxy resin containing a halogen flame retardant not only produces corrosive gases when burned, but also sometimes produces harmful carcinogenic gases such as dioxin and benzofuran. Therefore, using other elements to replace halogens to develop new halogen-free flame retardants is the current main development direction. [0004] Phosphorus-containing epoxy resin materials derived from phosphorus-based bisphenol (DOPOBQ) and DOPONQ have bette...

Claims

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Application Information

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IPC IPC(8): C07F9/6574C08G59/02C08G59/20
Inventor 林庆炫林宏泽张胜隆胡裕明
Owner 萧介夫
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