DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) derivative fire retardant and preparation method and application thereof

A derivative and flame retardant technology, applied in the field of DOPO derivative flame retardant and its preparation, can solve the problems of poor structural strength and compactness of carbon layer, decreased mechanical and mechanical properties, weak oxygen and heat insulation ability, etc. The effects of mechanical and mechanical properties, enhanced oxygen and thermal insulation capabilities, and enhanced compatibility

Active Publication Date: 2018-02-27
GUIZHOU MATERIAL IND TECH INSTITUE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, DOPO flame retardants also have their shortcomings. The charcoal layer formed by this type of flame retardant after combustion has poor structural strength and compactness, and weak oxygen and heat insulation capabilities; The compatibility between them is poor, so that the mechanical properties of this kind of flame retardants are reduced when they are used

Method used

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  • DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) derivative fire retardant and preparation method and application thereof
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  • DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) derivative fire retardant and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Preparation of DOPO derivative 1# of structural formula (1), there is 1 DOPO residue in this DOPO derivative:

[0069]

[0070] The synthetic route of DOPO derivative 1# is as follows:

[0071]

[0072] The synthesis method of DOPO derivative 1# is as follows:

[0073] Step 1 prepares DOPO-containing phenol derivatives 1

[0074] Add 12.2 g of p-hydroxybenzaldehyde and 10.9 g of p-aminophenol into a three-neck round bottom flask equipped with a magnetic stirrer, and then add 100 ml of methanol as a solvent. in N 2 The mixture was reacted at 50° C. for 6 hours in the atmosphere. The resulting aromatic group-containing Schiff base 1 (10.65g) and 21.6g of DOPO were dissolved in 100ml of tetrahydrofuran (THF), then in N 2 Under protective conditions, it was heated to 60°C and stirred for 12 hours to obtain a precipitate. The resulting precipitate was filtered and washed several times with THF at room temperature, then dried in a vacuum oven. The white product ob...

Embodiment 2

[0080] Prepare the DOPO derivative 2# of structural formula (2), there are 2 DOPO residues in this DOPO derivative:

[0081]

[0082] The synthetic route of DOPO derivative 2# is as follows:

[0083]

[0084]

[0085]

[0086] The synthetic method of DOPO derivative 2# is as follows:

[0087] Step 1 Preparation of DOPO-containing phenol derivatives 2

[0088] Add p-hydroxybenzaldehyde and p-phenylenediamine in a molar ratio of 2:1 (24.4g and 10.8g respectively) into a three-neck round bottom flask equipped with a magnetic stirrer, and then add 300ml of methanol as a solvent. in N 2 The mixture was reacted at 60° C. for 6 hours in the atmosphere, and the resulting precipitate was filtered and washed. Dry in an oven to obtain the Schiff base 2 containing aromatic groups. A mixture of the obtained product (31.6 g), 43.2 g of DOPO and 250 ml of tetrahydrofuran was heated to 60° C. and stirred for 12 hours to obtain a white precipitate. The resulting white precipit...

Embodiment 3

[0095] Prepare the DOPO derivative 3# of structural formula (3), there are 3 DOPO residues in this DOPO derivative:

[0096]

[0097] The synthetic route of DOPO derivative 3# is as follows:

[0098]

[0099]

[0100]

[0101] The synthesis method of DOPO derivative 3# is as follows:

[0102] Step 1 Synthesis of DOPO-DICY

[0103] Add DOPO and dicyandiamide (DICY) into the reaction vessel at a molar ratio of 1:1, heat to 175°C and react for 6 hours to obtain DOPO-DICY;

[0104] Step 2 prepares the Mannich type base containing DOPO

[0105] Add 0.01 mol of DOPO-DICY, 0.02 mol of p-hydroxybenzaldehyde and 100 ml of THF into a three-necked flask, blow nitrogen into it, and react at 50°C for 6 hours, and solids precipitate out. The obtained solid was filtered, washed with THF, and then dried in a vacuum oven to obtain Schiff base 3 containing an aromatic group.

[0106] The aromatic group-containing Schiff base 3 and DOPO were added to the three-necked flask accord...

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PUM

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Abstract

The invention discloses a DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) derivative fire retardant and a preparation method and application thereof. The DOPO derivative fire retardant contains a structure connected by a basic unit A-M-B and an additional unit, wherein the additional unit is an M unit, an M-A unit, an M-B unit, a DOPO derivative unit, a nitrile group, a nitrile group substituted DOPO derivate unit and / or DOPS derivate unit, and the condition is that A is a terminal unit, and B is an amido substituted DOPO derivate unit; A is a 1,3-diketone group-isobenzofuran-5-group-methanoyl monovalence group disclosed in the following formula (I); B is a bivalence amine group disclosed in the following formula (II) or (III); R1 and R2 are independently hydrogen, C1-C15 alkyl group or C6-C12 aryl groups, each m is independently 1,2,3 or 4, and M expresses direction connection or C6-C12 aryl groups. The DOPO derivative novel fire retardant is provided with a functional groupcompatible with an organic polymer, and the mechanical property and the antiflaming effect of a composite material which contains the fire retardant are improved. The formulas are shown in the description.

Description

technical field [0001] The invention relates to a flame retardant and a preparation method thereof, in particular to a DOPO derivative flame retardant and a preparation method thereof. Background technique [0002] At present, the flame retardants used in the market are mainly halogenated flame retardants, but the halogenated flame retardants release toxic smoke and gas during use, which is harmful to the environment and human health. Therefore, the development of halogen-free flame retardants is a very important direction. Phosphorus-based flame retardants are very important halogen-free flame retardants. Among phosphorus-based flame retardants, phosphorus-based flame retardants are an important direction of development at present. Phosphorous-phenanthrene-based flame retardants currently on the market Flame retardants include 9,10-dihydro-9oxa-10-phosphaphenanthrene-10-oxide (DOPO for short) and its derivatives. Due to the special structure of the molecule, this kind of p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08K5/5313C07F9/6574C08L67/02
CPCC07F9/657172C08K5/5313C08L2201/02C08L67/02
Inventor 张道海魏柯何敏秦舒浩于杰
Owner GUIZHOU MATERIAL IND TECH INSTITUE
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