KR102599672B1 - Method for producing organophosphorous flame retardant, flame retardant compound prepared thereby, and flame retardant polymer resin composition comprising the same - Google Patents

Abstract

The present invention relates to a method for producing an organophosphorus flame retardant, a flame retardant compound prepared thereby, and a flame retardant polymer resin composition containing the same. A method for producing an organophosphorus flame retardant according to an embodiment of the present invention includes dissolving a first compound represented by the following formula (1) in a solvent to form a first solution, and a second compound represented by the following formula (2). dissolving in a solvent to form a second solution; mixing the first and second solutions to react the first and second compounds to produce a third compound represented by the following formula (3): It may include the step of reacting the third compound with the fourth compound of Formula 4 below to produce a flame retardant compound represented by Formula 5 below.
[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

Description

Method for producing organophosphorous flame retardant, flame retardant compound prepared thereby, and flame retardant polymer resin composition comprising the same {Method for producing organophosphorous flame retardant, flame retardant compound prepared thereby, and flame retardant polymer resin composition comprising the same}

The present invention relates to a method for producing an organophosphorus flame retardant, a flame retardant compound produced thereby, and a flame retardant polymer resin composition containing the same, and to a technology for producing a flame retardant using eugenol.

Thermoplastic resins are applied to almost all electronic products due to their excellent processability and mechanical properties. However, thermoplastic resins themselves have characteristics that make them easily combustible and have no resistance to fire. Therefore, thermoplastic resins can easily combust due to an ignition source and can play a role in further spreading the fire. Considering this, countries such as the United States, Japan, and Europe are legally regulating the use of only polymer resins that meet flame retardant standards to ensure the safety of electronic products against fire.

In the past, a method of imparting flame retardant properties by applying halogen-based compounds and antimony-based compounds was often used to make thermoplastic resins flame retardant. Halogen-based compounds mainly used here include polybromodiphenyl ether, tetrabromobisphenol A, brominated epoxy compounds, and chlorinated polyethylene. Antimony trioxide and antimony pentoxide are mainly used as antimony compounds.

The method of imparting flame retardancy using halogen-based compounds and antimony-based compounds has an excellent flame retardant effect, and is a flame retardant with excellent cost-performance ratio, which is used in housing materials for electrical and office equipment, ABS resin, PS, PBT, PET, and epoxy. It is used as a major flame retardant for resins, etc. However, it has been reported through experiments that the hydrogen halide gas generated during processing has the potential to have a fatal effect on the human body. It is difficult to decompose in the environment, has high environmental persistence, and is not easily soluble in water, so it has high bioaccumulation. In particular, in the case of polybromodiphenyl ether, which is used as a representative halogen-based flame retardant, very toxic substances such as brominated dioxins or brominated furans are generated during combustion, so interest is focused on flame retardancy methods that do not use these halogen-based compounds.

Republic of Korea Patent Publication No. 10-2015-0045160

The present invention is intended to solve the above problems, and focuses on synthesizing an environmentally friendly organophosphorus flame retardant as a representative alternative to brominated flame retardants that emit components harmful to the human body and the environment when burned. In particular, eugenol, a bio-derived material, was selected as the starting material to ensure that it has excellent heat resistance and flame retardancy as an eco-friendly bio-based flame retardant.

In addition, to improve the flame retardancy, it was designed to include an alkoxyamine structure that can act as a radical scavenger to compensate for the shortcomings of organophosphorus flame retardants that require a high content. Therefore, alkoxyamine along with phosphorus can interfere with the combustion process by removing radicals generated during combustion, and thus can provide excellent flame retardant effects to polymer materials.

The problems to be solved by the present invention are not limited to the problems mentioned above, and other problems not mentioned can be clearly understood by those skilled in the art from the description below.

A method for producing an organophosphorus flame retardant according to an embodiment of the present invention to solve the above-described problem includes dissolving a first compound represented by the following formula (1) in a solvent to form a first solution, and formula (2) Dissolving a second compound represented by a solvent to form a second solution, mixing the first solution and the second solution, and reacting the first compound and the second compound, represented by the following formula 3: It may include producing a third compound and reacting the third compound with a fourth compound of the following Chemical Formula 4 to produce a flame retardant compound represented by the following Chemical Formula 5.

[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

Mixing the first solution and the second solution may be accomplished by adding the first solution to the second solution.

Hydrochloric acid generated during the reaction of the first compound and the second compound can be removed.

The solvent is N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N-benzyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl Sulfoxide, hexamethylphosphotriamide, N-acetyl-ε-caprolactam, dimethylimidazolidinone, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, γ-butyrolactone, dioxane, dioxolane, tetra It may be at least one selected from the group consisting of hydrofuran, chloroform, ethyl acetate, and methylene chloride.

When reacting the third compound and the fourth compound, a reaction initiator may be added.

The reaction initiator is 4,4'-azobis(4-cyanovaleric acid) [4-4,4'-Azobis(4-cyanovaleric acid)], 2,2'-azobis(2-methylpropiono) Nitrile)[2-2,2'-Azobis(2-methylpropionitrile)], Benzoyl Peroxide, 2,2-bis(t-butylperoxy)butane[2,2-Bis(tert-butylperoxy) )butane], 2,5-bis(t-butylperoxy)-2,5-dimethylhexane [2,5-Bis(tert-butylperoxy)-2,5-dimethylhexane], bis[1-(t-butyl) Peroxy)-1-methylethyl]benzene [Bis[1-(tert-butylperoxy)-1-methylethyl]benzene], t-butyl hydroperoxide [tert-Butyl hydroperoxide], t-butyl peracetate [tert- Butyl peracetate], t-Butyl peroxide [tert-Butyl peroxide], t-Butyl peroxybenzoate [tert-Butyl peroxybenzoate], Cumene hydroperoxide, Dicumyl peroxide, Lauro It may be at least one selected from the group consisting of Lauroyl peroxide, Peracetic acid, and Potassium persulfate.

A flame retardant compound according to an embodiment of the present invention for solving the above-mentioned problems is represented by the following formula (5).

[Formula 5]

A flame-retardant polymer resin composition according to another embodiment of the present invention for solving the above-described problems is prepared by the above-described method, and includes a flame retardant compound represented by the following formula (5) and an acrylate-based polymerization reaction with the flame retardant compound. It may include a compound or a styrene-based compound, and a solvent for dispersing the flame retardant compound and the acrylate-based compound or the styrene-based compound.

[Formula 5]

The acrylate-based compound is any selected from the group consisting of acrylate, methyl acrylate, ethyl acrylate, propyl acrylate, methacrylate, methyl methacrylate, ethyl methacrylate, acrylonitrile, and propyl methacrylate. It could be one.

The styrene-based compound may be α-methyl styrene or α-ethyl styrene.

The solvent may be any one selected from benzene, toluene, xylene, 1,4-dioxane, dichloromethane, and dichloroethane.

Additional cross-linking agents may be included.

The crosslinking agent is aryl methacrylate, 1,3-butylene glycol dimethacrylate, 1,3-butylene glycol diacrylate, divinylbenzene, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate. , triethylene glycol dimethacrylate, propylene glycol dimethacrylate, polyethylene glycol dimethacrylate, hexanediol dimethacrylate, trimethylolpropane trimethacrylate, triethylene glycol diacrylate, propylene glycol diacrylate , polyethylene glycol diacrylate, hexanediol diacrylate, trimethylolpropane triacrylate, diallyl phthalate, diallyl maleate, divinyl adipate, triallyl cyanurate, and triallyl isocyanate. There could be at least one.

It may be a flame-retardant polymer containing a cured product of the polymer resin composition.

The alkoxyamine-based organophosphorus flame retardant developed through the present invention was confirmed to be capable of excellent char formation at high temperatures through thermal property analysis. Therefore, it is believed that when a flame retardant is applied to a polymer material, it acts as a protective film in the condensation phase, thereby impeding combustion of the polymer material.

In addition, the flame retardant presented in the present invention shows the excellent flame retardant effect and has a hydroxy functional group capable of additional reactions. Accordingly, it is designed to have a structure that can be applied to not only additive but also reactive flame retardants, so it is expected to be easy to introduce into various polymer materials and is expected to be applicable to many industrial fields.

The effects of the present invention are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art from the description below.

Figure 1 is a flowchart showing a method for producing an organophosphorus flame retardant according to an embodiment of the present invention.
Figure 2 shows the results of nuclear magnetic resonance spectroscopy of the prepared flame retardant.
Figure 3 shows the results of Fourier transform infrared spectroscopy of the prepared flame retardant.
Figure 4 shows the results of evaluating the thermal stability of the flame retardant.
Figure 5 shows the results of evaluating the limiting oxygen index of flame retardants.

The advantages and features of the present invention and methods for achieving them will become clear by referring to the embodiments described in detail below along with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below and may be implemented in various different forms. The present embodiments are merely provided to ensure that the disclosure of the present invention is complete and to provide a general understanding of the technical field to which the present invention pertains. It is provided to fully inform the skilled person of the scope of the present invention, and the present invention is only defined by the scope of the claims.

The terminology used herein is for describing embodiments and is not intended to limit the invention. As used herein, singular forms also include plural forms, unless specifically stated otherwise in the context. As used in the specification, “comprises” and/or “comprising” does not exclude the presence or addition of one or more other elements in addition to the mentioned elements. Like reference numerals refer to like elements throughout the specification, and “and/or” includes each and every combination of one or more of the referenced elements. Although “first”, “second”, etc. are used to describe various components, these components are of course not limited by these terms. These terms are merely used to distinguish one component from another. Therefore, it goes without saying that the first component mentioned below may also be a second component within the technical spirit of the present invention.

Unless otherwise defined, all terms (including technical and scientific terms) used in this specification may be used with meanings commonly understood by those skilled in the art to which the present invention pertains. Additionally, terms defined in commonly used dictionaries are not interpreted ideally or excessively unless clearly specifically defined.

Hereinafter, embodiments of the present invention will be described in detail with reference to the attached drawings.

Prior to explanation, the meaning of terms used in this specification will be briefly explained. However, since the explanation of terms is intended to aid understanding of the present specification, it should be noted that if it is not explicitly described as limiting the present invention, it is not used in the sense of limiting the technical idea of the present invention.

Hereinafter, a method for producing an organophosphorus flame retardant according to an embodiment of the present invention, a flame retardant compound, and a polymer resin composition containing the same will be described.

First, we will look at the method for producing an organophosphorus flame retardant according to an embodiment of the present invention and the flame retardant compound produced thereby. 1 is a flowchart showing a method for producing an organophosphorus flame retardant according to the present invention. Referring to FIG. 1, the method for producing an organophosphorus flame retardant according to an embodiment of the present invention and the flame retardant compound produced thereby are described as follows.

First, the first compound represented by the following formula (1) is dissolved in a solvent to form a first solution (S10).

[Formula 1]

The first compound represented by Formula 1 is phenylphosphonic dichloride and can be dissolved using an organic solvent. The reason for dissolving the first compound is to induce a condensation reaction with the second compound, which will be described later.

Here, the solvent is N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N-benzyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, Dimethyl sulfoxide, hexamethylphosphotriamide, N-acetyl-ε-caprolactam, dimethylimidazolidinone, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, γ-butyrolactone, dioxane, dioxolane, It may be at least one selected from the group consisting of tetrahydrofuran, chloroform, ethyl acetate, and methylene chloride.

Subsequently, the second compound represented by the following formula (2) is dissolved in a solvent to form a second solution (S20).

[Formula 2]

The second compound represented by Formula 2 is eugenol, which can be dissolved using an organic solvent. The reason for dissolving the second compound is to induce a condensation reaction with the first compound described above. Here, any one of the organic solvents listed above may be selected as the solvent.

Subsequently, the first solution and the second solution are mixed, and the first compound and the second compound are reacted to produce a third compound represented by the following formula (3) (S30).

For example, phenylphosphonic dichloride, a first compound, is dissolved in ethyl acetate to form a first solution. The second compound, eugenol, is dissolved in ethyl acetate to form a second solution.

The first solution is gradually added to the formed second solution, and the first solution and the second solution are mixed. After mixing the first and second solutions, they are stirred at room temperature for 24 hours to react the first compound, phenylphosphonic dichloride, and the second compound, eugenol.

The first and second compounds are reacted to form a third compound represented by the following formula (3).

[Formula 3]

Meanwhile, the reaction in which the first compound and the second compound react to form the third compound is as follows.

During the above reaction, hydrochloric acid may be generated as a by-product, and this hydrochloric acid can be removed using triethylamine.

Subsequently, the third compound and the fourth compound of the following formula (4) are reacted to produce a flame retardant compound represented by the following formula (5) (S40).

[Formula 4]

When reacting the third compound and the fourth compound, a reaction initiator may be added. These reaction initiators are 4,4'-Azobis(4-cyanovaleric acid) [4-4,4'-Azobis(4-cyanovaleric acid)], 2,2'-azobis(2-methylpropionite) Lil)[2-2,2'-Azobis(2-methylpropionitrile)], Benzoyl Peroxide, 2,2-bis(t-butylperoxy)butane[2,2-Bis(tert-butylperoxy) butane], 2,5-bis(t-butylperoxy)-2,5-dimethylhexane [2,5-Bis(tert-butylperoxy)-2,5-dimethylhexane], bis[1-(t-butylperoxy) Oxy)-1-methylethyl]benzene [Bis[1-(tert-butylperoxy)-1-methylethyl]benzene], t-butyl hydroperoxide [tert-Butyl hydroperoxide], t-butyl peracetate [tert-Butyl peracetate], t-Butyl peroxide [tert-Butyl peroxide], t-Butyl peroxybenzoate [tert-Butyl peroxybenzoate], Cumene hydroperoxide, Dicumyl peroxide, lauroyl It may be at least one selected from the group consisting of peroxide (Lauroyl peroxide), peracetic acid, and potassium persulfate.

Through the reaction of the third compound and the fourth compound, a flame retardant compound represented by the following formula (5) may be formed.

[Formula 5]

Meanwhile, the reaction in which the third compound and the fourth compound react to form a flame retardant compound is as follows.

Next, we will look at a flame-retardant polymer resin composition according to another embodiment of the present invention.

A flame retardant polymer resin composition having flame retardancy according to an embodiment of the present invention is prepared according to the above example and includes a flame retardant compound represented by the following formula (5), and an acrylate-based compound or styrene-based compound that polymerizes with the flame retardant compound. It may include a compound, a solvent for dispersing the flame retardant compound, the acrylate-based compound, or the styrene-based compound.

[Formula 5]

Here, the acrylate-based compound is selected from the group consisting of acrylate, methyl acrylate, ethyl acrylate, propyl acrylate, methacrylate, methyl methacrylate, ethyl methacrylate, acrylonitrile, and propyl methacrylate. It can be any one selected. Additionally, the styrene-based compound may be α-methyl styrene or α-ethyl styrene.

Meanwhile, the solvent for dispersing the flame retardant compound, acrylate-based compound, or styrene-based compound may be any one selected from benzene, toluene, xylene, 1,4-dioxane, dichloromethane, and dichloroethane.

Meanwhile, the flame-retardant polymer resin composition according to an embodiment of the present invention may further include a crosslinking agent. Crosslinking agents can improve the mechanical strength of polymers by causing crosslinking between polymers that have undergone polymerization.

The crosslinking agent is aryl methacrylate, 1,3-butylene glycol dimethacrylate, 1,3-butylene glycol diacrylate, divinylbenzene, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, Triethylene glycol dimethacrylate, propylene glycol dimethacrylate, polyethylene glycol dimethacrylate, hexanediol dimethacrylate, trimethylolpropane trimethacrylate, triethylene glycol diacrylate, propylene glycol diacrylate, At least one selected from the group consisting of polyethylene glycol diacrylate, hexanediol diacrylate, trimethylolpropane triacrylate, diallyl phthalate, diallyl maleate, divinyl adipate, triallyl cyanurate, and triallyl isocyanate. It could be one.

By curing the flame-retardant polymer resin composition, a flame-retardant polymer can be produced.

Hereinafter, the present invention will be described in more detail through examples. These examples are only for illustrating the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited by these examples according to the gist of the present invention. .

Preparation example: Preparation of flame retardant compound

The alkoxyamine-based organophosphorus flame retardant presented in the present invention includes phenylphosphonic dichloride, eugenol, and 4-hydroxy TEMPO (4-hydroxy-2,2,6,6- It can be synthesized using tetramethylpiperidine-1-oxyl) as a starting material.

[phenylphosphonic dichloride]

[eugenol]

[4-hydroxy TEMPO; 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl)]

The synthesis of alkoxyamine-based organophosphorus flame retardants proceeds through a two-step reaction. The first synthesis step is a condensation reaction between phenylphosphonic dichloride and eugenol, and ethyl acetate is used as a solvent for synthesis.

After dissolving phenylphosphonic dichloride and eugenol in ethyl acetate, the phenylphosphonic dichloride solution is slowly added to the eugenol solution at 0°C. After completely adding the phenylphosphonic dichloride solution, stir at room temperature for 24 hours. At this time, triethylamine is used to collect hydrochloric acid (HCl) gas generated during the reaction, and triethylamine is added into the reactor along with eugenol. After completion of the reaction, only the product obtained through the reaction is extracted using distilled water and ethyl acetate. The ethyl acetate solution layer in which the product is dissolved is obtained, moisture is removed with magnesium sulfate, and the solvent is removed using a vacuum rotary concentrator to obtain the product of the first synthesis step.

[Product of the first synthesis step]

The second process proceeds through a reaction between the product obtained in the first synthesis step and hydroxy tempo, and di-tert-butyl peroxide is used to initiate the reaction. The product obtained in the first synthesis step, hydroxy tempo, and di-tert-butyl peroxide were added into the reactor and stirred at 110°C for 48 hours. After completion of the reaction, only the synthesized flame retardant is extracted using dichloromethane and distilled water. Afterwards, a dichloromethane solution layer in which the flame retardant is dissolved is obtained, moisture is removed with magnesium sulfate, and the solvent is removed using a vacuum rotary concentrator to obtain the flame retardant.

Additionally, column chromatography is used to obtain high purity flame retardants. The mobile phase solvent used in column chromatography was ethyl acetate and n-hexane in a 1:1 volume ratio, and silica was used as the stationary phase. By purifying by column chromatography, an alkoxyamine-based organophosphorus flame retardant according to the present invention is obtained.

[Flame retardant compound]

The entire synthesis process is as follows.

Experimental example: Measurement of physical properties of manufactured flame retardant compounds

The structures of the products and flame retardants obtained in each synthesis step are confirmed through nuclear magnetic resonance spectroscopy and Fourier transform infrared spectroscopy. These results are shown in Figures 2 and 3. The results showed that the flame retardant was synthesized.

Next, the thermal stability of the obtained flame retardant is confirmed using a thermogravimetric analyzer. The temperature range applied to the analysis is from room temperature to 700°C, and the analysis is conducted under a nitrogen atmosphere at a temperature increase rate of 10°C/min. When comparing the thermal stability of the product obtained in the first synthesis step and the finally synthesized flame retardant, the flame retardant developed in the present invention has a low initial decomposition temperature, but has a high residual amount of about 30 wt% at 700 ° C. These results are shown in Figure 4.

To confirm the flame retardant performance of the developed flame retardant, polylactide, a major biodegradable polymer, was selected as a matrix and samples were prepared through the solution casting method. In detail, polylactide and flame retardant are each dissolved in chloroform, and then the two solutions are mixed and stirred. The mixture stirred for 1 hour is placed in a glass mold, and then chloroform is slowly evaporated to obtain a polylactide sample. At this time, the flame retardant content in the sample is 0.3.5.7 weight percent (wt%) based on the weight of polylactide.

Flame retardant performance is analyzed through a limiting oxygen index test, and compared to pure polylactide, the limiting oxygen index of polylactide with added flame retardants increases significantly. For example, the limiting oxygen index of pure polylactide is about 19%, but the limiting oxygen index of polylactide with 3 weight percent of flame retardant added is about 33.5%. Ultimately, it can be seen that the alkoxyamine flame retardant developed in the present invention can provide excellent flame retardant effects with a small amount. These results are shown in Figure 5.

The alkoxyamine structure not only acts as a radical scavenger, but also enables a reversible reaction of C-O bonding by heat, and is expected to be applicable as an initiator of free radical polymerization.

The present invention designed a flame retardant structure to include an alkoxyamine structure capable of acting as a radical scavenger to compensate for the disadvantages of phosphorus-based flame retardants that require a high content to overcome flame retardancy.

The alkoxyamine-based organophosphorus flame retardant developed through the present invention was confirmed to be capable of excellent char formation at high temperatures through thermal property analysis. Therefore, it is believed that when a flame retardant is applied to a polymer material, it acts as a protective film in the condensation phase, thereby impeding combustion of the polymer material.

In addition, when a flame retardant is applied to polylactide, which is an actual biodegradable polymer, it has a higher limiting oxygen index compared to pure polylactide, so alkoxyamine-based organophosphorus flame retardants can greatly contribute to improving the flame retardancy of polymer materials. It seems possible.

The flame retardant presented in the present invention shows the above excellent flame retardant effect and has a hydroxy functional group capable of additional reactions. Accordingly, it is designed to have a structure that can be applied to not only additive but also reactive flame retardants, so it is expected to be easy to introduce into various polymer materials and can be applied to many industrial fields.

Additionally, the alkoxyamine structure contains a C-O bond that is reversible by heat and has a relatively stable radical tempo structure, so it is believed that it can be used as an initiator for free radical polymerization.

The alkoxyamine-based organophosphorus flame retardant presented in the present invention contains hydroxy groups at both ends, providing a wide range of applications, including not only additive flame retardants but also reactive flame retardants. Accordingly, we present a method for manufacturing an eco-friendly alkoxyamine-based organophosphorus flame retardant that is easy to apply to various polymer materials.

Because the alkoxyamine structure contains a bond capable of a reversible reaction by heat, it is believed to be applicable as an initiator for radical polymerization in the future. In other words, it provides a wide range of uses not only as a flame retardant but also as an initiator for polymer polymerization.

Above, embodiments of the present invention have been described with reference to the attached drawings, but those skilled in the art will understand that the present invention can be implemented in other specific forms without changing its technical idea or essential features. You will be able to understand it. Therefore, the embodiments described above should be understood in all respects as illustrative and not restrictive.

Claims (14)

Dissolving a first compound represented by Formula 1 below in a solvent to form a first solution;
Dissolving a second compound represented by the following formula (2) in a solvent to form a second solution;
mixing the first solution and the second solution, causing the first compound and the second compound to react to produce a third compound represented by the following formula (3); and
reacting the third compound with the fourth compound of formula 4 below to produce a flame retardant compound represented by formula 5 below and containing an alkoxyamine structure capable of acting as a radical scavenger; Manufacturing method.
[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]
According to claim 1,
Mixing the first solution and the second solution is a method for producing an organophosphorous flame retardant, characterized in that the first solution is added to the second solution. According to clause 2,
A method for producing an organophosphorous flame retardant, characterized in that hydrochloric acid generated during the reaction of the first compound and the second compound is removed. According to claim 1,
The solvent is N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N-benzyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl Sulfoxide, hexamethylphosphotriamide, N-acetyl-ε-caprolactam, dimethylimidazolidinone, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, γ-butyrolactone, dioxane, dioxolane, tetra A method for producing an organophosphorous flame retardant, characterized in that it is at least one selected from the group consisting of hydrofuran, chloroform, ethyl acetate and methylene chloride. According to claim 1,
A method for producing an organophosphorus flame retardant, characterized in that a reaction initiator is added during the reaction of the third compound and the fourth compound. According to clause 5,
The reaction initiator is 4,4'-azobis(4-cyanovaleric acid) [4-4,4'-Azobis(4-cyanovaleric acid)], 2,2'-azobis(2-methylpropiono) Nitrile)[2-2,2'-Azobis(2-methylpropionitrile)], Benzoyl Peroxide, 2,2-bis(t-butylperoxy)butane[2,2-Bis(tert-butylperoxy) )butane], 2,5-bis(t-butylperoxy)-2,5-dimethylhexane [2,5-Bis(tert-butylperoxy)-2,5-dimethylhexane], bis[1-(t-butyl) Peroxy)-1-methylethyl]benzene [Bis[1-(tert-butylperoxy)-1-methylethyl]benzene], t-butyl hydroperoxide [tert-Butyl hydroperoxide], t-butyl peracetate [tert- Butyl peracetate], t-Butyl peroxide [tert-Butyl peroxide], t-Butyl peroxybenzoate [tert-Butyl peroxybenzoate], Cumene hydroperoxide, Dicumyl peroxide, Lauro A method for producing an organophosphorus flame retardant, characterized in that it is at least one selected from the group consisting of Lauroyl peroxide, Peracetic acid, and Potassium persulfate. A flame retardant compound manufactured by any one of claims 1 to 6, represented by the following formula (5), and comprising an alkoxyamine structure capable of acting as a radical scavenger.
[Formula 5]
In a flame retardant polymer resin composition having flame retardancy.
A flame retardant compound prepared according to any one of claims 1 to 6, represented by the following formula (5), and containing an alkoxyamine structure capable of acting as a radical scavenger;
An acrylate-based compound or styrene-based compound that polymerizes with the flame retardant compound; and
A flame-retardant polymer resin composition comprising the flame retardant compound and a solvent for dispersing the acrylate-based compound or the styrene-based compound.
[Formula 5]
According to clause 8,
The acrylate-based compound is any selected from the group consisting of acrylate, methyl acrylate, ethyl acrylate, propyl acrylate, methacrylate, methyl methacrylate, ethyl methacrylate, acrylonitrile, and propyl methacrylate. A flame retardant polymer resin composition, characterized in that one. According to clause 8,
A flame retardant polymer resin composition, wherein the styrene-based compound is α-methyl styrene or α-ethyl styrene. According to clause 8,
A flame-retardant polymer resin composition, wherein the solvent is any one selected from benzene, toluene, xylene, 1,4-dioxane, dichloromethane, and dichloroethane. According to clause 8,
A flame retardant polymer resin composition further comprising a crosslinking agent. According to claim 12,
The crosslinking agent is aryl methacrylate, 1,3-butylene glycol dimethacrylate, 1,3-butylene glycol diacrylate, divinylbenzene, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate. , triethylene glycol dimethacrylate, propylene glycol dimethacrylate, polyethylene glycol dimethacrylate, hexanediol dimethacrylate, trimethylolpropane trimethacrylate, triethylene glycol diacrylate, propylene glycol diacrylate , polyethylene glycol diacrylate, hexanediol diacrylate, trimethylolpropane triacrylate, diallyl phthalate, diallyl maleate, divinyl adipate, triallyl cyanurate, and triallyl isocyanate. A flame retardant polymer resin composition comprising at least one flame retardant resin composition. A flame retardant polymer comprising a cured product of the flame retardant polymer resin composition according to claim 8.