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Diallyl phosphorus-containing bio-based diacid ester and its preparation method and use

A technology of bio-based diacid diallyl ester and bio-based diacid diglycidol, which is applied in the field of halogen-free flame retardants to achieve the effects of saving resources, improving compatibility, and good flame retardant properties

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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  • Diallyl phosphorus-containing bio-based diacid ester and its preparation method and use
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  • Diallyl phosphorus-containing bio-based diacid ester and its preparation method and use

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Effect test

Embodiment 1

[0045] Embodiment 1 (preparation of phosphorous-containing itaconic acid)

[0046] 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.

[0047]

[0048] Formula II

Embodiment 2

[0049] Embodiment 2 (preparation of phosphorus-containing butenedioic acid)

[0050] 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.

[0051]

[0052] Formula II

Embodiment 3

[0054] 100g of the phosphorus-containing itaconic acid prepared in Example 1, 900g of tetrahydrofuran, 400g of allyl chloride and 300g of potassium carbonate were reacted at 40°C for 72 hours, filtered, washed with water, and evaporated under reduced pressure to remove the solvent and water to obtain the phosphorus-containing coating Diallyl conate (structure shown in formula I, n=1). The phosphorus-containing diallyl itaconate 1 H NMR spectrum as figure 1 as shown, 1 The appearance of 5.25ppm and 5.8ppm in the H NMR spectrum represents the H on the allyl double bond, and other peaks are consistent with the H proton shift of phosphorus-containing diallyl itaconate, proving that the obtained substance is phosphorus-containing Diallyl itaconate (structure shown in formula I, n=1).

[0055]

[0056] Formula I

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Abstract

The invention discloses a diallyl phosphorus-containing bio-based diacid ester and its preparation method and use. The diallyl phosphorus-containing bio-based diacid ester has a structure shown in the formula I, and in the formula I, n is equal to 0 or 1. The diallyl phosphorus-containing bio-based diacid ester can be used as a fire retardant and can be used for preparation of a nonsaturated polyester. The invention also discloses a preparation method of the diallyl phosphorus-containing bio-based diacid ester. The preparation method utilizes itaconic acid, fumaric acid or maleic acid having abundant biological sources as a raw material to realize modification of DOPO. The preparation method has dual effects of saving resources and protecting environment. The invention also discloses a use of a diglycidyl phosphorus-containing bio-based diacid ester. Based on a diglycidyl phosphorus-containing bio-based diacid ester, through introduction of an epoxy group, the diglycidyl phosphorus-containing bio-based diacid ester is obtained and has a structure shown in the formula III, and in the formula III, n is equal to 0 or 1. The diglycidyl phosphorus-containing bio-based diacid ester can be used as a fire retardant and can be used for preparation of epoxy resin.

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 diallyl diacid and phosphorus-containing bio-based diglycidyl diacid, their 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 Hazar...

Claims

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Application Information

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IPC IPC(8): C07F9/6574C08F220/32C08F222/20C08G59/42C08G59/30
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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