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
View PDF5 Cites 8 Cited by
  • 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 derivat

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Diallyl phosphorus-containing bio-based diacid ester and its preparation method and use
  • Diallyl phosphorus-containing bio-based diacid ester and its preparation method and use
  • Diallyl phosphorus-containing bio-based diacid ester and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0045] Example 1 (Preparation of itaconic acid containing phosphorus)

[0046] 100g of itaconic acid, 167g of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 300g of toluene and 10g of 1% chloroplatinic acid isopropanol solution ( 1% refers to the mass percentage of chloroplatinic acid), mixed uniformly, 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 of formula II , Where n=1.

[0047]

[0048] Formula II

Example Embodiment

[0049] Example 2 (Preparation of Phosphobutenedioic Acid)

[0050] 100g maleic acid or fumaric acid, 170g 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 500g xylene and 10g mass percentage is 1% Chloroplatinic acid isopropanol solution (1% refers to the mass percentage of chloroplatinic acid), mix well, react at 130°C for 12 hours, filter, wash with acetone, and dry to obtain phosphobutenedioic acid, namely Phosphorus-containing bio-based diacids of formula II structure, where n=0.

[0051]

[0052] Formula II

Example Embodiment

[0053] Example 3

[0054] 100g of 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 distilled under reduced pressure to remove solvent and water to obtain a phosphorus-containing coating Diallyl aconic acid (structure as shown in formula I, n=1). The phosphorus-containing diallyl itaconate 1 The H NMR spectrum is shown 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 the phosphorus-containing diallyl itaconic acid, which proves that the obtained substance is phosphorus-containing Diallyl itaconate (structure shown in formula I, n=1).

[0055]

[0056] Formula I

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Glass transition temperatureaaaaaaaaaa
Tensile strengthaaaaaaaaaa
Glass transition temperatureaaaaaaaaaa
Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap