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Phosphorus-containing compound, epoxy resin composition, molded plastic product, preparation method and application

A technology for epoxy resins and compounds, which is applied in the field of preparation of phosphorus-containing compounds and their preparations, their cured products, epoxy resin compositions, phosphorus-containing compounds, and molding plastic products, and can solve the problem of high material brittleness and limited application range and other problems, to achieve the effect of improving toughness and flame retardancy, excellent comprehensive performance, and avoiding migration and precipitation

Active Publication Date: 2020-12-11
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the reactive phosphorus-based flame retardants disclosed in the above-mentioned inventions all have relatively high rigidity, and when applied to epoxy resin systems, the prepared materials are highly brittle and the scope of application is limited

Method used

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  • Phosphorus-containing compound, epoxy resin composition, molded plastic product, preparation method and application
  • Phosphorus-containing compound, epoxy resin composition, molded plastic product, preparation method and application
  • Phosphorus-containing compound, epoxy resin composition, molded plastic product, preparation method and application

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preparation example Construction

[0041] Another aspect of the embodiments of the present invention provides a method for preparing a phosphorus-containing compound, comprising:

[0042] (1) Reacting the aldehyde or ketone compound represented by formula (II) with the compound represented by formula (III) to obtain a dialdehyde or diketone compound, the dialdehyde or diketone compound having the following formula (IV) Structure shown:

[0043]

[0044]

[0045] In formula (II), (III), (IV), n, R 0 , R 2 , R 3 、Ar 2 The definition of is consistent with formula (I), that is, n is any integer from 2 to 50, and R 0 Selected from C1~C6 alkylene, C1~C6 alkyleneoxy or C3~C7 cycloalkylene, R 2 selected from -COO-, -CONH-, -NHCOO-, -NHCONH- or -O-, R 3 Selected from hydrogen atom, C1~C6 alkyl group, C1~C6 alkoxyl group, substituted or unsubstituted phenyl group, Ar 2 selected from substituted or unsubstituted phenyl, R 4 and R 5 are independently selected from carboxyl groups, ester groups, acid chloride g...

Embodiment 1

[0103] (1) Dissolve 100 mole parts of p-hydroxybenzaldehyde, 30 mole parts of 1,12-dichlorododecane and 5 wt% sodium hydroxide of the weight of aldehyde compounds in 1000 ml of water, and react at 0°C for 36 hours to obtain di Aldehyde compound, its structure is shown in the following formula, and the nuclear magnetic spectrum is as follows figure 1 Shown:

[0104]

[0105] (2) React 100 mol parts of dialdehyde compound obtained above, 200 mol parts of DOPO, 600 mol parts of guaiacol and 0.50 wt% p-toluenesulfonic acid of DOPO weight at 80°C for 36 hours to obtain phosphorus-containing The compound, its structure is shown in the following formula, and the NMR spectrum is as follows figure 2 Shown:

[0106]

[0107] (3) 100 parts by mass of bisphenol A epoxy resin and 250 parts by mass of the obtained phosphorus-containing compound were uniformly mixed, cured at 120°C for 1 hour, and cured at 160°C and 220°C for 2 hours each to obtain a cured epoxy resin product. The ...

Embodiment 2

[0109] (1) Dissolve 100 mole parts of p-hydroxybenzaldehyde, 40 mole parts of 1,6-dibromohexane and 100 wt% potassium hydroxide of the weight of aldehyde compounds in 1500 ml of water, and react at 80°C for 24 hours to obtain dialdehyde base compound, its structure is shown in the following formula:

[0110]

[0111] (2) 100 molar parts of the dialdehyde compound obtained above, 200 molar parts of DOPO, 1000 molar parts of guaiacol and 5 wt% methanesulfonic acid of the weight of DOPO were reacted at 130°C for 12 hours to obtain a phosphorus-containing compound, Its structure is shown in the following formula:

[0112]

[0113] (3) 100 parts by mass of bisphenol A epoxy resin and 200 parts by mass of the obtained phosphorus-containing compound were evenly mixed, cured at 120°C for 1 hour, and cured at 160°C and 220°C for 2 hours each to obtain a cured epoxy resin product. The flame retardancy of the obtained cured product reaches UL-94 V0 level, and the impact strength i...

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Abstract

The invention discloses a phosphorus-containing compound, and the invention also discloses a flexible phosphorus-containing epoxy resin curing agent, which includes the phosphorus-containing compound. The invention also discloses the preparation method and application of the phosphorus-containing compound, the epoxy resin composition and the cured product of the halogen-free flame-retardant epoxy resin. The phosphorus-containing compound provided by the present invention has relatively high content of phosphorus elements, flexible chain segments and active groups, and can be used as a reactive epoxy resin curing agent, avoiding the problem of migration and precipitation of small-molecule added flame retardants, ensuring that the material It has excellent flame retardant properties and endows the material with relatively good toughness, which is suitable for a wider range of applications.

Description

technical field [0001] The invention relates to a phosphorus-containing compound, in particular to a phosphorus-containing compound and a preparation method thereof, as well as an epoxy resin composition, its cured product, a preparation method of a molded plastic product and its application, and belongs to the technical field of polymer materials . Background technique [0002] Epoxy resin is one of the most commonly used thermosetting resins, and it is widely used in various fields of national economy. But on the one hand, the limiting oxygen index (LOI) of ordinary epoxy resin is low, and it is a flammable material. Its flammability and continuous spontaneous combustion after leaving the fire are easy to cause fire; The rigid benzene ring structure makes epoxy resin materials generally very brittle. The characteristics of flammability and brittleness greatly restrict the application of epoxy resin. Therefore, it is of great significance to improve the toughness and flam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6568C07F9/6574C08G59/62C08G59/50B32B17/04B32B17/12B32B27/04B32B27/38B32B27/26B32B33/00
CPCB32B5/02B32B5/26B32B27/26B32B27/38B32B33/00B32B2250/05B32B2250/20B32B2260/023B32B2260/046B32B2262/101B32B2307/3065B32B2307/558C07F9/65685C07F9/657172C08G59/504C08G59/621
Inventor 刘小青江艳华腾娜代金月
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI