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Phosphorus-containing biological based diacid diglycidyl ester and preparation method and application thereof

A bio-based diglycidyl diacid and bio-based diacid diglycidyl technology are applied in the field of halogen-free flame retardants to achieve the effects of saving resources, improving mechanical strength and heat resistance, and improving compatibility

Active Publication Date: 2014-08-06
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although U.S. Patent 7,342,061, 20060247344, and 20100181696 all disclose technical solutions for modifying DOPO by itaconic acid, maleic acid and fumaric acid, these technical solutions only prepare DOPO derivatives containing two carboxyl groups, DOPO derivatives containing two double bonds or two epoxy groups that can directly participate in the curing of unsaturated polyesters and epoxy resins have not been involved

Method used

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  • Phosphorus-containing biological based diacid diglycidyl ester and preparation method and application thereof
  • Phosphorus-containing biological based diacid diglycidyl ester and preparation method and application thereof
  • Phosphorus-containing biological based diacid diglycidyl ester and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0037] Embodiment 1 (preparation of phosphorous-containing itaconic acid)

[0038] 100g itaconic acid, 167g9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 300g toluene and 10g mass percent are 1% isopropanol solution of chloroplatinic acid ( 1% refers to the mass percentage of chloroplatinic acid), mixed evenly, reacted at 120°C for 12 hours, filtered, washed with acetone and dried to obtain phosphorus-containing itaconic acid, which is a phosphorus-containing bio-based diacid with the structure of formula II , where n=1.

[0039]

[0040] Formula II

Embodiment 2

[0041] Embodiment 2 (preparation of phosphorus-containing butenedioic acid)

[0042] 100g of maleic acid or fumaric acid, 170g of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 500g of xylene and 10g of 1% by mass Chloroplatinic acid isopropanol solution (1% refers to the mass percentage of chloroplatinic acid), mixed evenly, reacted at 130°C for 12 hours, filtered, washed with acetone, and dried to obtain phosphorus-containing butenedioic acid, namely A phosphorus-containing bio-based diacid with a structure of formula II, wherein n=0.

[0043]

[0044] Formula II

Embodiment 3

[0046] Fully mix 100g of the phosphorus-containing butenedioic acid prepared in Example 2, 400g of epichlorohydrin, 200g of N,N-dimethylformamide and 6g of cetyltrimethylammonium chloride, and react at 100°C for 3 hour, then lower the temperature to 70°C, add 60g of calcium hydroxide and 20g of water, and continue to react for 3 hours, after washing, removing the solvent and drying, the phosphorus-containing butenedioic acid diglycidyl ester is obtained.

[0047] The above-mentioned obtained phosphorobutenedioic acid diglycidyl ester is carried out structural characterization, according to its hydrogen nuclear magnetic resonance spectrogram, it can be known that in 1 H NMR (CD 3 Cl is the solvent), 7.3-8.3ppm represents the proton peak on the DOPO benzene ring, and 2.3-3.5ppm represents the characteristic chemical shift of the epoxy group and the proton on the main chain carbon. The epoxy value measured by hydrochloric acid acetone method is 0.15. Using the epoxy value via t...

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Abstract

The invention discloses a phosphorus-containing biological based diacid diglycidyl ester with a structure as shown in a formula I, wherein n is 0 or 1, and m satisfies the relation of 0<m<=15. In the preparation of epoxy resin, the phosphorus-containing biological based diacid diglycidyl ester can participate in curing, the introduction of DOPO does not consume epoxy groups of epoxy resin, the compatibility of DOPO with epoxy resin can be enhanced, and the strength and the glass transition temperature of epoxy resin will not be decreased but can even be improved. The invention also provides a preparation method of the phosphorus-containing biological based diacid diglycidyl ester. Itaconic acid, fumaric acid or maleic acid with rich biological sources are used as raw materials to modify DOPO, so as to reduce or avoid the use of petrochemical products from the source and realize the double effects of saving resources and environmental protection.

Description

technical field [0001] The invention relates to the field of halogen-free flame retardants, in particular to a novel halogen-free flame retardant derived from 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and bio-based diacids Flame retardant-phosphorous bio-based diacid diglycidyl ester and its preparation method and application. Background technique [0002] Because polymer materials have the characteristics of good performance, light weight, and easy processing, they have been widely used in various fields of the national economy. However, polymer materials are flammable, and it is often necessary to add flame retardants to meet the requirements of use. With the EU's two major environmental directives on flame retardants, the "Waste Electrical and Electronic Equipment Directive, WEEE" (effective in March 2003) and the "Restriction of Hazardous Substances in Electrical and Electronic Equipment" (Restriction of Hazardous Substances Directive, RoHS), traditiona...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574C08G59/12C08G59/42C08G59/30
Inventor 马松琪刘小青江艳华朱锦冯建湘樊利波
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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