JP2002088005A - Bromine compound and flame-retardant resin composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a bromine compound having low metal corrosivity, and hardly changing the color at the melt processing time at a high temperature, and further to provide a thermoplastic resin composition having the low metal corrosivity, capable of providing a molded product having good color, and having excellent flame retardance. SOLUTION: This bromine compound is characterized in that the SO42- ion concentration measured by an ion chromatography is <=100 ppm. The flame retardant resin composition comprising (A) 100 pts.wt. thermoplastic resin, (B) 1-50 pts.wt. bromine compound and (C) 0-25 pts.wt. inorganic flame retardant auxiliary is characterized in that the SO42- ion concentration measured by the ion chromatography is <=10 ppm.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a bromine compound having low metal corrosiveness and little change in color tone during high-temperature melt processing, and a flame-retardant resin composition using the same.

[0002]

2. Description of the Related Art Organic polymer materials are used in various applications because of their excellent moldability, mechanical properties, and electrical properties. Among them, high impact polystyrene (HIPS) resins, styrene resins such as ABS resins and polyolefin resins are inexpensive in addition to excellent properties. It is widely used for various purposes including building materials and automotive parts.

[0003] Further, since these organic polymer materials are generally flammable, the burning of organic substances may cause disasters that threaten the safety of people, and it is necessary to take measures to make such organic polymer materials nonflammable. With regard to flame retardancy of organic polymer materials, various regulations, including UL standards, have been strengthened and required.

[0004] In general, the flame retardation of an organic polymer material is performed by adding a flame retardant to the organic polymer material, blending a flame retardant resin, and using a reactive flame retardant monomer. Is carried out by a method such as reforming.

[0005] As a method for making a thermoplastic resin such as a styrene resin or a polyolefin resin flame retardant, various bromine-containing compounds have been conventionally proposed. For example, to make styrene resin flame-retardant, 2,2
There is known a method of blending -bis [(3,5-dibromo-4-allyloxy) phenyl] propane (Japanese Patent Publication No. 60-8019), hexabromocyclododecane (Japanese Patent Publication No. 43-29658) or the like with such a resin. Have been.

Further, as a flame retardant having higher thermal stability,
2,2-bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] propane (JP-A-60-240750, etc.), bis [@ 3,5-dibromo-4] A method of blending-(2,3-dibromopropyloxy) @phenyl] sulfone (Japanese Patent Application Laid-Open No. 60-240750, etc.) with such a styrene-based resin is known, and flame retardation of a polyolefin-based resin is known. Also, as a flame retardant, 2,2-bis [@ 3,5-dibromo-4-
(2,3-dibromopropyloxy) @phenyl] propane (JP-B 5-82856, etc.), bis [@ 3,
5-dibromo-4- (2,3-dibromopropyloxy) {phenyl] sulfone (Japanese Patent Publication No. 50-35103)
Is known in the art.

However, when a resin composition containing these bromine compounds is kneaded and melt-molded along with high-temperature molding for improving molding efficiency, the inside of the kneader, the mold of the molding machine or The screw may be corroded, and when the conductor is insert-molded, rust may be generated on the conductor of the molded body, resulting in disconnection. Further, there is a problem that the obtained molded product has inferior hue.

[0008]

SUMMARY OF THE INVENTION The present inventors have developed a thermoplastic resin composition having low metal corrosiveness, little change in color tone during high-temperature melt processing, good molded product color tone, and excellent flame retardancy. As a result of intensive studies for the purpose of providing, by controlling the specific impurities contained in the bromine compound and the resin composition used as a flame retardant to a specific amount or less, the inside of the kneader during high-temperature melt processing is controlled. , The corrosiveness of the molding machine mold or screw is reduced, and the color change is small,
The present inventors have found that a thermoplastic resin composition having good color tone and excellent flame retardancy of a molded article can be obtained, and have reached the present invention.

[0009]

That is, according to the present invention, there is provided a bromine compound characterized by having an SO ₄ ^2- ion concentration of 200 ppm or less as measured by an ion chromatography method.

Here, the SO ₄ ²⁻ ion concentration measured by the ion chromatography method is determined by dissolving the bromine compound in an organic solvent immiscible with water, for example, methylene chloride, adding water to the solution, mixing the solution, The aqueous phase separated and recovered was measured by ion chromatography.

In the bromine compound of the present invention, the SO ₄ ²⁻ ion concentration measured by the ion chromatography method is 200 p.
pm or less. It is difficult to completely remove the sulfur compound in the obtained bromine compound, and the concentration of the SO ₄ ^2- ion is preferably 0.01 to 200 ppm, more preferably 0.1 to 200 ppm.
01-100 ppm is more preferable, and 0.01-50 p
pm is more preferable, and 0.01 to 30 ppm is particularly preferable. If the SO ₄ ^2- ion concentration exceeds 200 ppm, the thermal stability of the bromine compound decreases, and the thermal stability of the resin composition containing the bromine compound in the thermoplastic resin decreases, causing metal corrosion and color tone. Is undesirably reduced.

As the bromine compound of the present invention, a crude solution containing a bromine compound is obtained by a bromination reaction using bromine, and then the unreacted bromine remaining in the crude solution is reduced. It is preferable to carry out a reduction treatment using a sulfur compound as a reducing agent and then recover the same.

The sulfur compound used as a reducing agent is
Examples thereof include sodium bisulfite, sodium dithionite, sodium sulfite, hydrogen sulfide and hydroxylamine sulfate. Among them, sodium bisulfite, sodium dithionite and sodium sulfite are preferably used.

As the bromine compound of the present invention, specifically,
Bromine compounds represented by the following (I) to (X) are exemplified.

(I) Compound represented by the following formula (1)

[0016]

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(Wherein, m, n, p, and q are integers of 1 to 6, and Ar ¹ and Ar ² may be the same or different, and are divalent aromatics having 5 to 16 carbon atoms.) Y is a kind selected from methylene, propylene, isopropylidene, isobutylidene, cyclohexylidene, sulfone, ketone and a single bond, and R ¹ and R ² are each a hydrocarbon group having 2 to 6 carbon atoms. Is.)

(II) Compound represented by the following formula (3)

[0019]

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(Where x and y are integers of 1 to 6, preferably 1 to 4, and Ar ³ and Ar ⁴ may be the same or different, and may have 5 to 5 carbon atoms). 16 aromatic hydrocarbon groups, preferably a phenyl group, a tolyl group, a xylyl group or a naphthyl group, and Z is one selected from methylene, propylene, isopropylidene, isobutylidene, cyclohexylidene, sulfone, ketone and a single bond, Preferably, it is one selected from methylene, isopropylidene, isobutylidene, cyclohexylidene, sulfone, and a single bond, and T ³ and T ⁴ are each a hydrogen atom or a saturated hydrocarbon group having 1 to 6 carbon atoms, preferably hydrogen Atoms, methyl, ethyl, propyl, isopropyl, butyl, and isobutyl.)

(III) Compound represented by the following formula (4)

[0022]

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(In the formula, r is an integer of 10 to 10000, and s is 1 to 5.) This compound is preferably a brominated polystyrene having a bromine content of 40 to 70% and a number average molecular weight of 10,000 or more. .

(IV) Compound represented by the following formula (5)

[0025]

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(Wherein R ¹⁵ , R ¹⁶ and R ¹⁷ may be the same or different and represent a hydrogen atom, an alkyl group, a brominated alkyl group, a phenoxyl group or a brominated phenoxyl group). Examples of are methyl, ethyl, propyl and the like, examples of brominated alkyl groups include dibromoethyl and dibromopropyl, and examples of phenoxyl groups include phenoxyl and methylphenoxyl groups. Examples of the brominated phenoxyl group include dibromophenoxyl and tribromophenoxyl, and among them, tribromophenoxyl is preferable. In particular,
Tris (2,3-dibromopropyl) isocyanurate is exemplified.

(V) Compound represented by the following formula (6)

[0028]

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(In the formula, g and h are each an integer of 1 to 5, preferably g and h are each 5 and may be the same or different, and i is an integer of 1 to 4, preferably 2 Is shown.)

(VI) Compound represented by the following formula (7)

[0031]

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(In the formula, j and k are integers of 1 to 5, preferably j and k are both 5 and may be the same or different.)

(VII) Compound represented by the following formula (8)

[0034]

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[0035]

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[0036] (wherein, R ³ to R ⁸ are the same or different atom or functional group, a hydrogen atom or an alkyl group, a brominated alkyl group, a brominated aryl group. However, R ³
At least one of to R ⁸ is a brominated aryl group represented by the formula (9). l is an integer of 1 to 4, u is 1 to
Indicates an integer of 5. Examples of the above alkyl group include methyl, ethyl, propyl and the like, examples of the brominated alkyl group include dibromoethyl and dibromopropyl, and examples of the brominated aryl group include dibromophenyl and tribromophenyl. There are phenyl, tetrabromophenyl, pentabromophenyl and the like, and among them, tribromophenyl, tetrabromophenyl and pentabromophenyl are preferable. Specifically, octabromo-1,1,3-trimethyl-3-phenylindane is exemplified.

(VIII) Compound represented by the following formula (10)

[0038]

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(Wherein R ¹¹ , R ¹² and R ¹³ may be the same or different and represent a hydrogen atom, an alkyl group, a brominated alkyl group, a phenoxyl group or a brominated phenoxyl group).
Examples of the alkyl group include methyl, ethyl, propyl and the like, examples of the brominated alkyl group include dibromoethyl and dibromopropyl, and examples of the phenoxyl group include a phenoxyl and methylphenoxyl group. Examples of the brominated phenoxyl group include dibromophenoxyl and tribromophenoxyl, and among them, tribromophenoxyl is preferable. In particular,
2,4,6-tris (tribromophenoxy) -1,
3,5-triazine is exemplified.

(IX) Compound represented by the following formula (11)

[0041]

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(Wherein d and e are integers of 1 to 4, preferably 4 are both the same or different, and f is an integer of 1 to 4, preferably 2) Shown.)

(X) Compound represented by the following formula (12)

[0044]

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[0045]

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[0046]

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(Wherein R ⁹ and R ¹⁰ may be the same or different and each is a hydrogen atom, the above formula (13) or (14)
It is expressed by an equation. o, v, w, and z are integers of 0 to 4 (provided that
At least one is an integer of 1 or more), and t represents an integer of 0 to 100. R ¹⁴ in the above formula (14) represents a hydrogen atom or a brominated aryl group. )

Among the bromine compounds (I) to (X), the bromine compounds (I) to (VII) are subjected to a bromination reaction in the latter half of the reaction step, followed by reduction and neutralization, It is preferable from the viewpoint of recovering a desired bromine compound.
The bromine compound (IV) is more preferable, and the bromine compound (I) is particularly preferable.

The bromine compound preferably used in the present invention is represented by the above formula (1), wherein m, n, p and q in the formula (1) are integers of 1 to 6, preferably 1 to 4 Ar ¹ and Ar ² may be the same or different, and are a divalent aromatic hydrocarbon group having 5 to 16 carbon atoms, preferably a phenyl group, a tolyl group, a xylyl group or a naphthyl group, Y is one selected from methylene, propylene, isopropylidene, isobutylidene, cyclohexylidene, sulfone, ketone and a single bond, preferably methylene, isopropylidene, isopropylidene,
R ¹ and R ² are each a saturated hydrocarbon group having 2 to 6 carbon atoms, preferably an ethyl group, a propyl group, an isopropyl group, a butyl group and an isobutyl group. is there.

As the bromine compound represented by the above formula (1), specifically, 2,2-bis [｛3,5-dibromo-
4- (2,3-dibromopropyloxy) @phenyl]
Propane, 2,2-bis [@ 3,5-dibromo-4-
(2,3-dibromo-2-methylpropyloxy) @phenyl] propane, bis [@ 3,5-dibromo-4-
(2,3-dibromopropyloxy) @phenyl] methane, bis [{3,5-dibromo-4- (2,3-dibromo-2-methylpropyloxy)} phenyl] methane,
Bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] sulfone, bis [{3
5-dibromo-4- (2,3-dibromo-2-methylpropyloxy) {phenyl] sulfone, {3,3 ',
5,5'-tetrabromo-4,4 '-(2,3-dibromopropyloxy)} biphenyl, {3,3', 5
5'-tetrabromo-4,4 '-(2,3-dibromo-
2-methylpropyloxy)} biphenyl and {3
3 ', 5,5'-tetrabromo-4,4'-(1,2-
Dibromoethyloxy)｝ biphenyl;
2-bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] propane, bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] Methane and bis [｛3,5-
Dibromo-4- (2,3-dibromopropyloxy)
Phenyl] sulfone is preferred, and 2,2-bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] propane is particularly preferably used.

The bromine compound represented by the above formula (1) is specifically a bromine compound produced by an addition reaction of bromine (Br ₂ ). This addition reaction is a reaction for brominating an unsaturated bromine compound represented by the following formula (2).

[0052]

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(Wherein, the definitions of Ar ¹ , Ar ² , Y, m and n mean the same as in the above formula (1). Q)
¹ and Q ² represent a C 2-6 hydrocarbon group having one or two identical or different unsaturated groups. In the above formula (2), Ar ¹ , Ar ² , Y, m and n
Means the same as in the above formula (1), and the preferred definition also means the same. Specific examples of the hydrocarbon group for Q ¹ and Q ² include a vinyl group, an allyl group and an isobutenyl group, and preferably an allyl group.

As the unsaturated bromine compound represented by the above formula (2), specifically, 2,2-bis {(3,5-dibromo-4-allyloxy) phenyl} propane, 2,2-bis} (3,5-dibromo-4-isobutenyloxy) phenyl} propane, bis {(3,5-dibromo-4-allyloxy) phenyl} methane, bis {(3,5-dibromo-4-isobutenyloxy) ) Phenyl methane,
(3,3 ′, 5,5′-tetrabromo-4,4′-diallyloxy) biphenyl, (3,3 ′, 5,5′-tetrabromo-4,4′-divinyloxy) biphenyl, bis {(3 , 5-Dibromo-4-allyloxy) phenyl
Sulfone and bis {(3,5-dibromo-4-isobutenyloxy) phenyl} sulfone, and the like,
Among them, 2,2-bis {(3,5-dibromo-4-allyloxy) phenyl} propane, 2,2-bis} (3,5
-Dibromo-4-isobutenyloxy) phenyl {propane, bis} (3,5-dibromo-4-allyloxy)
Phenyl {methane, bis {(3,5-dibromo-4-isobutenyloxy) phenyl} methane, (3,3 ′, 5,
5′-tetrabromo-4,4′-diallyloxy) biphenyl and (3,3 ′, 5,5′-tetrabromo-4,
4'-divinyloxy) biphenyl is preferable, and 2,2-bis {(3,5-dibromo-4-allyloxy) is more preferable.
Phenyl {propane, 2,2-bis {(3,5-dibromo-4-isobutenyloxy) phenyl} propane, bis {(3,5-dibromo-4-allyloxy) phenyl}
Methane and bis {(3,5-dibromo-4-isobutenyloxy) phenyl} methane are more preferred, especially 2,2-bis {(3,5-dibromo-4-allyloxy)
Phenyldipropane is preferably used.

The reaction between the unsaturated bromine compound and bromine is as follows:
The reaction is carried out in the presence of a solvent, which is inert without adversely affecting the reaction. The higher the solubility of the solvent for the unsaturated bromine compound is, the more preferable it is, but the solvent may be partially soluble. Further, it is preferable that the bromine compound generated by the bromination reaction of the unsaturated bromine compound is substantially dissolved in the solvent.

The solvent in the bromination reaction is not only used as a mere solvent for performing the reaction uniformly, but also preferably functions as a solvent for effectively removing the heat of reaction out of the system. Have. Therefore, it is advantageous that the solvent has a normal pressure boiling point of 0 to 100 ° C., preferably 20 to 90 ° C. In particular, when the reaction heat is substantially removed by the heat of vaporization of the solvent, the normal pressure boiling point is 20 ~ 80 ° C, especially 20 ~
A range of 60 ° C. is desirable.

Examples of the solvent include halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, 1,1-dichloroethane, bromoethane, butyl chloride, chloropropane, diethyl ether, ethyl isopropyl ether, tetrahydrofuran, dioxane and the like. Examples thereof include ether hydrocarbon compounds and aromatic hydrocarbon compounds such as toluene. Also, bromine can be used as a solvent.

Of these solvents, halogenated hydrocarbons are preferred, and methylene chloride and chloroform are particularly preferred as solvents. These solvents are used alone or in combination of two or more. These halogenated hydrocarbons can also be used as a mixed solvent with dioxane.

The amount of bromine used in the bromination is as follows:
In order to improve the rate of addition of bromine to the unsaturated groups of the unsaturated bromine compound, the reaction is carried out using an excess of bromine with respect to the unsaturated groups. The bromine content is preferably in the range of 1.1 to 3 molecules per unit.

In the bromination, bromine itself or a bromine solution is used. As the solvent used in the bromine solution, the same solvent as described above is used, and in this case, the concentration of bromine is preferably in the range of 10 to 90% by weight.

In the bromination method, as a specific means, a solution in which an unsaturated bond compound is dissolved in a solvent inert to the reaction is mixed with bromine or a bromine solution to form an unsaturated compound and bromine. Is reacted. At the time of this bromination reaction, it is preferable to remove a substantial amount of the heat of the bromination reaction by a solvent or the heat of vaporization of bromine. The substantial amount of the heat of reaction means at least 80%, preferably at least 85% of the theoretical calorific value generated by the desired bromination reaction.

As described above, the reaction temperature in the bromination reaction is preferably a temperature at which a substantial amount of the heat of the bromination reaction is removed by the heat of vaporization of bromine or the solvent, and such a bromination reaction is limited to normal pressure. Instead, it can be performed under pressure or under reduced pressure. The reaction temperature can be controlled by operating pressure, depending on the type of solvent used (boiling point) and the amount of bromine. Usually, the reaction temperature is in the range of 0 to 60 ° C, preferably in the range of 5 to 55 ° C, particularly preferably 10 to 55 ° C.
A range of ５０50 ° C. is advantageous.

After the completion of the reaction, unreacted bromine (Br ₂ ) remains in the reaction mixture, and the residual bromine adversely affects the purification step and the recovery step. Is desirable.

This chemical treatment employs a method in which residual bromine in the reaction mixture is treated with a reducing agent, bromine is converted into hydrobromic acid, and then hydrobromic acid is neutralized with an alkaline neutralizing agent. Is done. The method is carried out by adding a reducing agent and a neutralizing agent to the reaction mixture.

As the reducing agent used in this treatment method, a sulfur compound used in a usual reduction reaction is preferable. Specifically, sodium hydrogen sulfite, sodium dithionite, sodium sulfite, hydrogen sulfide and hydroxyl sulfate Examples thereof include amines, and sodium bisulfite, sodium dithionite and sodium sulfite are particularly preferably used. These reducing agents can also be used as an aqueous solution. These reducing agents are used alone or in combination of two or more.

Examples of the alkaline neutralizing agent include alkali metal hydroxides, alkali metal carbonates, alkaline earth metal hydroxides and alkaline earth metal carbonates. Sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, calcium hydroxide, calcium carbonate, and the like are preferable, and sodium hydroxide is particularly preferably used. These alkaline neutralizing agents are preferably used as an aqueous solution. Also,
These alkaline neutralizing agents are used alone or in combination of two or more.

In the above treatment method, 2 mol or more, preferably 2 to 3 mol, per mol of residual bromine in the reaction mixture.
0 mol, more preferably 2.2 to 15 mol, even more preferably 2.5 to 10 mol of reducing agent are added to the reaction mixture. When less than 2 mol of reducing agent is added,
Bromine remains in the mixture, and a low-purity brown colored bromine compound is obtained, which is not preferable. Further, 2 mol or more, preferably 2 to 50 mol, more preferably 2.2 to 30 mol, and still more preferably 2.5 to 20 mol of an alkaline neutralizing agent per 1 mol of the residual bromine in the reaction mixture. Is added to the reaction mixture. When the amount of the neutralizing agent to be added is less than 2 mol, hydrogen bromide remains in the aqueous solution, and this strong acid aqueous solution cannot be discarded as it is. In addition, some hydrogen bromide remains in the mixture, which easily corrodes metals. Furthermore, this hydrogen bromide has a strong irritating odor, which is not preferable in a working environment.

The reducing agent and the alkaline neutralizing agent include:
The bromine compound and the bromine-containing reaction mixture are added simultaneously or separately. Such a reducing agent and a neutralizing agent may be added separately or in advance, but it is preferable to add them separately since there is no possibility that the reducing agent may cause a side reaction due to alkali. As the addition method, a method in which a reducing agent is added followed by a neutralizing agent is preferably adopted.

In the treatment method, the reaction mixture to which the reducing agent and the alkaline neutralizing agent are added is mixed so that the reducing and neutralizing reactions proceed smoothly.

The weight ratio of the reaction mixture to the aqueous phase at the time of performing the reduction and neutralization reactions is 20:80 to 80:
20 is preferable, 30:70 to 70:30 is more preferable, and 40:60 to 60:40 is particularly preferable. Within this range, the reduction and neutralization reactions proceed efficiently, and bromine is removed in a short time. Therefore, when performing reduction and neutralization reactions,
It is preferable to add water or a solvent to the reaction mixture so as to fall within the above range.

The time required for the reduction and neutralization of bromine in the reaction mixture is preferably 2 minutes or more, more preferably 2 to 90 minutes, still more preferably 5 to 60 minutes, and more preferably 10 to 45 minutes.
Minutes are particularly preferred.

After the above-mentioned reduction treatment and neutralization treatment, the reaction mixture (organic phase) can be separated from the aqueous phase to obtain a bromine compound solution.

The bromine compound solution is usually recovered by adding a poor solvent to the solution and depositing the solution. However, the bromine compound recovered by such a method is subjected to a reducing agent such as sodium bisulfite, sodium dithionite, sodium sulfite, hydrogen sulfide and hydroxylamine sulfate used in the above reduction treatment, Generated SO ₄ ²⁻ , HSO ₄ ⁻ , HS
A large amount of salts or ions such as sulfuric acid and sodium sulfate containing O ₃ ⁻ and SO ₃ ²⁻ or sulfur compounds such as SO ₂ remain.

The remaining amount of the sulfur compound is measured as the SO ₄ ²⁻ ion concentration by the above-mentioned ion chromatography method.
In this measurement method, the sulfate group component in each of the above sulfur compounds is oxidized to SO ₄ ²⁻ ions during sample treatment and measurement, and the total amount of the remaining amounts of various sulfur compounds is SO ₄
Measured as ^2- ion concentration.

The SO ₄ ^2- ion concentration of the present invention is 200 pp
As a method for obtaining a bromine compound having a molecular weight of m or less, a purification method in which a bromine compound is dissolved in a good solvent, the dissolved solution is washed several times with water, and a sulfur compound is extracted can be preferably used.

The good solvent is a solvent which can dissolve the bromine compound at a concentration of 5% or more by weight at 20 ° C. and is immiscible with water, for example, methylene chloride, chloroform, 1,2-dichloroethane. , 1,1-
Dichloroethane is preferred, and methylene chloride is particularly preferably used. These good solvents are used alone or in combination of two or more. As the water washing method, a method such as a batch-type water washing method by adding water to a solution in which the bromine compound is dissolved in a good solvent, stirring the mixture, and then allowing it to stand or centrifuge, or a continuous-type water washing method in a continuous method is used. Can be The water to be used may be any of acidic water, neutral water and alkaline water.

The bromine compound obtained by such a purification method is dried by a known drying method such as using a conduction heating type drying device such as a reduced pressure dryer or a hot air heating type drying device.

Also, in the present invention, (A) 100 parts by weight of a thermoplastic resin, (B) 1 to 50 parts by weight of a bromine compound and (C) 0 to 25 parts by weight of an inorganic flame retardant aid. A plastic resin composition having an SO ₄ ²⁻ ion concentration of 10 as measured by an ion chromatography method.
Provided is a flame-retardant resin composition characterized by being at most ppm.

In the resin composition of the present invention, the SO ₄ ²⁻ ion concentration measured by the ion chromatography method is 10 pp.
m or less. It is difficult to completely remove the sulfur compound in the resin composition, and the SO ₄ ^2- ion concentration is preferably 0.001 to 10 ppm, and 0.001 to 8 ppm.
pm is more preferable, 0.001 to 5 ppm is still more preferable, 0.001 to 3 ppm is still more preferable,
0.001 to 1 ppm is particularly preferred. If the SO ₄ ²⁻ ion concentration exceeds 10 ppm, the thermal stability of the resin composition decreases, causing metal corrosion and decreasing the color tone, which is not preferable.

Here, the SO ₄ ²⁻ ion concentration measured by the ion chromatography method is determined by dissolving the above resin composition in an organic solvent immiscible with water, for example, methylene chloride, adding water to this solution, and mixing. And the recovered aqueous phase was measured by ion chromatography.

The thermoplastic resin (A) used in the present invention includes, for example, polyolefin resin, polystyrene resin, polyvinyl chloride resin, polyamide resin, polyester resin, polycarbonate resin, polyphenylene ether resin and the like. Among them, polyolefin resins and polystyrene resins are preferably used.

The polyolefin resin is a homopolymer or a copolymer of olefins such as ethylene, propylene and butene, or a copolymer with a component copolymerizable with these olefins. Polypropylene, ethylene-vinyl acetate copolymer,
Ethylene-ethyl acrylate copolymer, ethylene-acrylic acid copolymer, ethylene-methyl methacrylate copolymer, ethylene-α-olefin copolymer, ethylene-propylene copolymer and propylene-butene copolymer, etc. Among them, polypropylene is preferably used.

The polystyrene resin refers to a resin containing a vinyl aromatic monomer as a constituent component. Examples of the vinyl aromatic monomer include styrene, o-methylstyrene and p-methylstyrene.
Nuclear alkyl-substituted styrenes such as -methylstyrene, m-methylstyrene, 2,4-dimethylstyrene, ethylstyrene and p-tert-butylstyrene, and α-alkyls such as α-methylstyrene and α-methyl-p-methylstyrene Examples include a halogen-substituted styrene such as substituted styrene, monobromostyrene, dibromostyrene, and tribromostyrene. Specifically, polystyrene, polymethylstyrene, rubber-modified styrene resin (HIPS), acrylonitrile-styrene copolymer (AS resin), acrylonitrile-butadiene-styrene copolymer (ABS resin), acrylonitrile-acryl rubber-styrene copolymer Polymer (AAS resin), acrylonitrile-ethylene propylene rubber-styrene copolymer (AES resin), methyl methacrylate-butadiene-styrene copolymer (MBS
HIPS and ABS resins are preferable, and HIPS is particularly preferably used.

Such a rubber-modified styrene resin (HIPS)
The term "polymer" refers to a polymer in which a rubber-like polymer is dispersed in the form of particles in a matrix composed of a polystyrene resin, and in the presence of the rubber-like polymer, styrene and, if necessary, a vinyl monomer copolymerizable therewith. By subjecting the monomer mixture to known bulk polymerization, bulk suspension polymerization, solution polymerization or emulsion polymerization. The polymerization method may be one-stage polymerization or multi-stage polymerization. Examples of the diene rubber component forming this rubbery polymer include polybutadiene, polyisoprene, styrene-butadiene copolymer,
Rubbers such as butadiene-isoprene copolymer, ethylene-propylene copolymer, and natural rubber are preferably used, and the proportion is preferably 5 to 80% by weight in the HIPS resin component.

The ABS resin is a graft copolymer obtained by graft-polymerizing an aromatic vinyl compound component and a vinyl cyanide compound component capable of graft copolymerization with a diene rubber component as a base. Examples of the diene rubber component include polybutadiene and styrene-butadiene copolymer.Examples of the aromatic vinyl compound component grafted to these diene rubber components include styrene and α.
-Methylstyrene, p-methylstyrene, alkoxystyrene, halogenated styrene and the like, among which styrene is preferably used, and examples of the vinyl cyanide compound component include acrylonitrile, methacrylonitrile, chloroacrylonitrile, and the like. Among them, acrylonitrile is preferably used.
Further, methyl acrylate, ethyl acrylate, butyl acrylate, octyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, octyl methacrylate, maleic anhydride, N-substituted maleimide and the like can be used. Such a graft copolymer,
It may be produced by any polymerization method such as bulk polymerization, solution polymerization, suspension polymerization and emulsion polymerization, and the grafting method may be a single-stage graft or a multi-stage graft. Further, a blend of a vinyl copolymer obtained by separately copolymerizing the aromatic vinyl compound component and the vinyl cyanide compound component with a graft copolymer can also be preferably used. These thermoplastic resins can be used alone or in combination of two or more.

The bromine compound (B) used in the resin composition of the present invention is SO ₄ measured by an ion chromatography method.
^{The same} thing as the above-mentioned bromine compound whose ^2- ion concentration is 200 ppm or less is preferably used.

In the flame-retardant resin composition of the present invention, as the (C) inorganic flame-retardant auxiliary used as required, the flame-retardant is increased by interaction with a bromine compound. There are, specifically, antimony trioxide, antimony pentoxide, boron trioxide, zinc borate, red phosphorus and the like, among which antimony trioxide and antimony pentoxide are particularly preferred.

The proportion of each component in the flame-retardant resin composition is 1 to 50 parts by weight, preferably 1.5 to 30 parts by weight, and more preferably 1.5 to 30 parts by weight based on 100 parts by weight of the thermoplastic resin. 15 parts by weight is more preferable, and 2.5 to 10
A part by weight is more preferable, and 3 to 8 parts by weight is particularly preferable. If the amount is less than 1 part by weight, the flame-retardant effect is low, and 50
When the amount is more than the weight part, the thermal stability of the flame-retardant resin composition is lowered, and the mechanical properties are lowered.
Further, based on 100 parts by weight of the thermoplastic resin, the inorganic flame retardant is 0 to 25 parts by weight, preferably 0.1 to 20 parts by weight, more preferably 0.2 to 15 parts by weight, .
Particularly preferred is 3 to 10 parts by weight. If the amount is more than 25 parts by weight, the mechanical properties deteriorate, which is not preferable.

The flame-retardant resin composition of the present invention is obtained by blending these components in the above-mentioned mixing ratio, and using a Henschel mixer, a tumbler mixer, a super mixer, a Banbury mixer, a kneader, a roll, a single screw extruder, a twin screw extruder. It is manufactured by appropriately using a method of mixing and kneading with a machine or the like.

The flame-retardant resin composition of the present invention may contain a colorant, a pigment, a stabilizer, a plasticizer, a lubricant, an ultraviolet absorber, a filler, a reinforcing agent, a foaming agent, and other additives as required. Can be blended.

The flame-retardant resin composition obtained according to the present invention is extremely useful as a material for various applications including housings for home electric appliances and OA equipment, indoor and outdoor decorations, building materials, automobile parts and the like.

[0092]

Hereinafter, the present invention will be described in detail with reference to Examples.
Of course, it is not limited to this. The evaluation was performed according to the following methods (1) to (9).

(1) Purity of bromine compound The purity of the bromine compound was measured by high performance liquid chromatography (LC-6A manufactured by Shimadzu Corporation) at 280 n.
The measurement was performed by a method for detecting the absorption of m. The purity of the bromine compound was determined from the peak area ratio of each component obtained from this chromatography.

[0094] ⁽²⁾ SO ₄ ^2- ion concentration of SO ₄ ^2-ion concentration bromine compound bromine compound can be prepared by dissolving the sample 10g was added to methylene chloride 10 ml, water 10 to the solution
Then, the mixture was mixed with a shaker for 1 hour, the aqueous phase was collected by centrifugation, and the SO ₄ ²⁻ ion extracted into the water was subjected to ion chromatography (Dionex 2).
000i / SP) using a method of detecting by electrical conductivity. By comparing the peak area of each component obtained by this chromatography with the standard, SO _{4 was obtained.}
^{The 2-} ion concentration was determined, and the SO ₄ ^2- ion concentration in the bromine compound was calculated.

[0095] (3) SO ₄ ^2- ion concentration of SO ₄ ^2-ion concentration resin composition in the resin composition is dissolved 12 hours standing with the addition of sample 20g of methylene chloride 40 ml,
Further, 20 ml of water was added, the mixture was mixed for 1 hour with a shaker, the aqueous phase was collected by centrifugation, and the SO ₄ ²⁻ ion extracted into the water was subjected to ion chromatography (Dion).
ex (2000i / SP), using a method of detecting by electrical conductivity. By comparing the peak area of each component obtained by this chromatography with the standard, the SO ₄ ^2- ion concentration was determined, and the SO ₄ in the resin composition was determined.
^{The 2-} ion concentration was calculated. The detection limit was 1 ppm.

(4) Melt color of bromine compound A 2 g sample was charged with 2,2-bis [@ 3,5-dibromo-4-
For (2,3-dibromopropyloxy) @phenyl] propane, 150 [deg.] C. and bis [{3,5-dibromo-
4- (2,3-dibromopropyloxy) @phenyl]
Methane was heated at 130 ° C and bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] sulfone at 210 ° C for 1 hour using a hot air circulating dryer to melt. .

After the melt was cooled, 20 mL of methylene chloride was added to dissolve the melt, and the whole was placed in a colorimetric tube for chromaticity measurement, and methylene chloride was added to the 50 mL mark line. Then, under colorimetric lighting, the melt solution and the same volume of the Hazen color number standard solution are compared with the naked eye from above, and a color number standard solution corresponding to the color of the melt solution is selected. The standard solution number was expressed as a melt color. The larger the number, the greater the degree of coloring (from light yellow to dark brown), indicating that the thermal stability of the sample is inferior.

(5) pH The pH of the bromine compound was determined by dissolving 150 g of the bromine compound in 300 mL of methylene chloride, adding 50 mL of water having a pH of 7 and stirring for 30 minutes, and then measuring the pH of the recovered aqueous layer.
A lower pH indicates a higher acidity of the bromine compound,
Indicates high metal corrosion.

(6) Simple rust test (bromine compound) A 10 g sample was put into a glass bottle, an iron nail whose surface plating was stripped off with hydrochloric acid was inserted, and heated for 2 hours with a hot-air circulating drier kept at 40 ° C. The surface condition of the nail afterwards was visually observed. Here, when rust is generated, it indicates that the metal has corrosiveness, and the higher the degree of rust, the higher the metal corrosiveness.

(7) Heat resistance of the resin composition A sample was injected into an injection molding machine (SJ-25B manufactured by Meiki Seisakusho Co., Ltd.).
, Test pieces (length 70 mm, width 50 mm, thickness 2 mm) were prepared, respectively, with and without a stagnation at a molding temperature of 230 ° C. or 190 ° C. for 10 minutes, and the change in hue (ΔE) thereof was measured. The change in hue is JISZ-8
730, color difference meter (SE-200 manufactured by Nippon Denshoku Co., Ltd.)
0), the respective L, a, and b values were measured and calculated by the following equation. ΔE = ｛(LL ′) ² + (aa ′) ² + (bb ′)
² ｝ ^1/2 (L, a, b are not retained, L ', a', b 'are retained for 10 minutes)

(8) Flame Retardancy The flame retardancy was evaluated using a test piece having a thickness of 3.18 mm (1/8 inch) according to the vertical combustion test method specified in UL-94 of the UL standard. In addition, no of the evaluation result
tV means a rejected product with less than V rank. The oxygen index (OI value) according to JIS K-7201 was measured.

(9) Rust test (resin composition) A 2 cm diameter, 2 mm thick disk-shaped metal piece made of KPS-6 (SKD-11 modifier) was placed on a glass petri dish, and a pellet-shaped metal piece was placed on the test piece. Place 10 g of the resin composition and 23
The resin was melted by heating with a hot air dryer at 0 ° C. for 2 hours, and after cooling, the resin was taken out, the solidified resin and the metal piece were peeled off, and the surface condition of the metal piece was observed. Here, when rust is generated, it has metal corrosiveness, and the higher the degree of rust, the higher the metal corrosiveness.

Comparative Example 1 A flask equipped with a stirrer, a condenser, a thermometer and a dropping funnel was charged with 2,2-bis {(3,5-dibromo-4-allyloxy) phenyl}.
200 g (0.32 mol) of propane and 340 g of methylene chloride were added and dissolved. Next, while maintaining this solution at 35 ° C. and stirring, 161.3 g (1.01 mol) of bromine was added dropwise from the dropping funnel over 30 minutes. After the dropwise addition, the reaction solution was further stirred at the same temperature for 30 minutes to complete the bromine addition reaction.

Next, excess bromine in the reaction solution was reduced with 120 g of a 15% by weight aqueous sodium bisulfite solution,
The produced hydrogen bromide was neutralized using a 25% by weight aqueous sodium hydroxide solution. Thereafter, a methylene chloride layer was separated from this solution, and about 90% of the methylene chloride was evaporated and removed from the methylene chloride layer.
L was added to precipitate a reaction product, and the precipitate was filtered to remove a massive solid. This lumpy solid is crushed in a mortar,
It was dried under reduced pressure at 665 Pa at 80 ° C. for 10 hours.
Bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] propane was obtained. The bromine compound has a purity of 90.2% and an SO ₄ ²⁻ ion concentration of 21.
0 ppm, melt color was 160, pH was 4.0, and rust was generated in the simple rust test.

[Comparative Example 2] In Comparative Example 1, 2,2-
Instead of 200 g of bis {(3,5-dibromo-4-allyloxy) phenyl} propane, bis {(3,5-dibromo-4-allyloxy) phenyl} sulfone 206
g [0.32 mol], except that the reaction and treatment were carried out in the same manner as in Comparative Example 1 to obtain bis [｛3,5-dibromo-4-
(2,3-Dibromopropyloxy) {phenyl] sulfone was obtained. The purity of this bromine compound is 86.9%,
O ₄ ^2- ion concentration is 216 ppm, molten color is 160, p
H was 3.8, and rust was generated in the simple rust test.

[Comparative Example 3] In Comparative Example 1, 2,2-
Instead of 200 g of bis {(3,5-dibromo-4-allyloxy) phenyl} propane, 190 g of bis {(3,5-dibromo-4-allyloxy) phenyl} methane
(0.32 mol), except that reaction and treatment were carried out in the same manner as in Comparative Example 1 to obtain bis [｛3,5-dibromo-4-
(2,3-Dibromopropyloxy) {phenyl] methane was obtained. The bromine compound has a purity of 56.8% and SO ₄
^{The 2-} ion concentration was 224 ppm, the melt color was 300, the pH was 3.5, and rust was generated in the simple rust test.

[Example 1] The 2,2- obtained in Comparative Example 1
100 g of bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] propane is placed in a flask equipped with a stirrer, and 200 g of methylene chloride is dissolved therein. After that, 100 g of water was added, and stirring was further continued at room temperature for 1 hour.
After completion of the stirring, the mixture was allowed to stand for about 2 hours to separate an upper aqueous layer and a lower methylene chloride layer. After performing the same operation a total of three times, about 90% of methylene chloride was evaporated and removed from the methylene chloride layer, and 400 mL of methanol was added thereto to precipitate a reaction product. The precipitate was filtered to remove a massive solid. I took it out. This lump solid was pulverized in a mortar and dried under reduced pressure at 665 Pa at 80 ° C. for 10 hours to give 2,2-bis [｛3,5
-Dibromo-4- (2,3-dibromopropyloxy) {phenyl] propane was obtained. The bromine compound had a purity of 90.5%, an SO ₄ ^2- ion concentration of 5 ppm, a melt color of 50, a pH of 6.5, and no rust was generated in the simple rust test.

[Example 2] In Example 1, 2,2-
The procedure was performed except that 100 g of bis {(3,5-dibromo-4-allyloxy) phenyl} sulfone synthesized in Comparative Example 2 was used instead of 100 g of bis {(3,5-dibromo-4-allyloxy) phenyl} propane. After washing and treatment with water in the same manner as in Example 1, bis [@ 3,5-dibromo-
4- (2,3-dibromopropyloxy) @phenyl]
I got a sulfone. The purity of the bromine compound is 87.0.
%, SO ₄ ²⁻ ion concentration is 9 ppm, melt color is 90, p
H was 6.4, and no rust was generated in the simple test.

[Example 3] In Example 1, 2,2-
Bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] methane synthesized in Comparative Example 3 in place of 100 g of bis {(3,5-dibromo-4-allyloxy) phenyl} propane Water washing and treatment were carried out in the same manner as in Example 1 except for using 100 g to obtain bis [{3,5-dibromo-4- (2,3-dibromopropyloxy)} phenyl] methane. The bromine compound has a purity of 60.1%, an SO ₄ ²⁻ ion concentration of 7 ppm,
The melt color was 250, the pH was 6.0, and no rust was generated in the simple test.

[0110]

[Table 1]

[Example 4] High impact polystyrene resin [HIPS; Stylon 492 manufactured by Asahi Kasei Corporation)
R-H27-71], 6 parts of the bromine compound obtained in Example 1 and 0.6 part of antimony trioxide were added to 100 parts, and mixed with a tumbler-type blender, followed by a twin-screw extruder [Ikekai Iron Works Co., Ltd. ) PCM-30] at a cylinder temperature of 160 ° C. Then, using the pellets, an injection molding machine [SJ-25B manufactured by Meiki Seisakusho Co., Ltd.]
Was molded at a molding temperature of 220 ° C. The obtained pellets were subjected to SO ₄ ^2- ion concentration measurement and rust test, and the obtained test pieces were subjected to flammability evaluation and thermal stability evaluation. The results are shown in Table 2.

[Embodiment 5] In Embodiment 4, Embodiment 1
Except that the bromine compound obtained in Example 2 was used instead of the bromine compound obtained in Example 2, pelletization and a test piece were formed in the same manner as in Example 1, and the SO ₄ ^2- ion concentration measurement, rust Test, flammability evaluation and thermal stability evaluation,
The results are shown in Table 2.

[Embodiment 6] In Embodiment 4, Embodiment 1
Except that the bromine compound obtained in Example 3 was used instead of the bromine compound obtained in Example 3, pelletization and a test piece were formed in the same manner as in Example 1, and the SO ₄ ^2- ion concentration measurement, rust Test, flammability evaluation and thermal stability evaluation,
The results are shown in Table 2.

Example 7 Pellets and test pieces were prepared in the same manner as in Example 1 except that 1.0 part of antimony pentoxide was used instead of 0.6 part of antimony trioxide. It was molded and subjected to SO ₄ ^2- ion concentration measurement, rust test, flammability evaluation, and thermal stability evaluation. The results are shown in Table 2.

[Embodiment 8] In Embodiment 4, Embodiment 1
Except that 6 parts of the bromine compound obtained in the above was used and 10 parts of antimony trioxide was not used, a pellet was formed and a test piece was formed in the same manner as in Example 1, and the SO ₄ ²⁻ ion concentration measurement, rust test, Conducted flammability evaluation and thermal stability evaluation,
The results are shown in Table 2.

Example 9 Polypropylene resin [PP;
8 parts of the bromine compound obtained in Example 1 and 4 parts of antimony trioxide were added to 100 parts of K-1016 (manufactured by Chisso Petrochemical Industries, Ltd.) and mixed with a tumbler-type blender, followed by a twin-screw extruder [ Ikegai Iron Works Co., Ltd. PCM-30]
Into a pellet at a cylinder temperature of 160 ° C. Next, a test piece was molded at 190 ° C. using an injection molding machine [SJ-25B manufactured by Meiki Seisakusho Co., Ltd.] using the pellets. The obtained pellets were subjected to SO ₄ ^2- ion concentration measurement and rust test, and the obtained test pieces were subjected to flammability evaluation and thermal stability evaluation. The results are shown in Table 2.

Comparative Example 4 In Example 4, Example 1
Except for using the bromine compound obtained in Comparative Example 1 in place of the bromine compound obtained in Example 1, pelletizing and forming a test piece in the same manner as in Example 1, measuring the SO ₄ ^2- ion concentration, Test, flammability evaluation and thermal stability evaluation,
The results are shown in Table 2.

[Comparative example 5]
Except that the bromine compound obtained in Comparative Example 2 was used in place of the bromine compound obtained in Example 1, pelletization and a test piece were formed in the same manner as in Example 1, and the SO ₄ ^2- ion concentration measurement, rust Test, flammability evaluation and thermal stability evaluation,
The results are shown in Table 2.

[Comparative example 6]
Except that the bromine compound obtained in Comparative Example 3 was used in place of the bromine compound obtained in Example 1, pelletization and a test piece were formed in the same manner as in Example 1, and the SO ₄ ²⁻ ion concentration measurement, rust Test, flammability evaluation and thermal stability evaluation,
The results are shown in Table 2.

[0120]

[Table 2]

[0121]

EFFECTS OF THE INVENTION The bromine compound and the flame retardant resin composition of the present invention have low metal corrosiveness, little change in color tone during high-temperature melt processing, good color tone of molded products obtained, and high flame retardancy. Therefore, the industrial effect is exceptional.

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (reference) C08K 3/00 C08K 3/00 5/00 5/00 C08L 101/00 C08L 101/00 F term (reference) 4F071 AA14 AA22 AB18 AC03 AC06 AC12 AC19 AE07 AH16 BB05 4H006 AA01 AA02 AD30 BA02 BA36 GN24 GP03 GP20 GP22 TA02 TB13 TB40 4J002 BB031 BB051 BB061 BB071 BB081 BB121 BB151 BC031 BC061 BC081 BC091 BC111 CB121 CB131 EB131 BN 001 EU196 FD132 FD136 FD137

Claims (14)

[Claims] 1. SO ₄ measured by an ion chromatography method
^2- A bromine compound having an ion concentration of 200 ppm or less. 2. The bromine compound is obtained by performing a bromination reaction using bromine to obtain a crude solution containing the bromine compound, and then reducing the unreacted bromine remaining in the crude solution during the reduction treatment. The bromine compound according to claim 1, wherein the bromine compound is subjected to a reduction treatment using a sulfur compound as an agent and then recovered. 3. The bromine compound according to claim 2, wherein the sulfur compound is sodium bisulfite, sodium dithionite, sodium sulfite, hydrogen sulfide or hydroxylamine sulfate. 4. The bromine compound according to claim 1, wherein the bromine compound is represented by the following formula (1). Embedded image (Where m, n, p, and q are integers of 1 to 6,
Ar ¹ and Ar ² may be the same or different and are a divalent aromatic hydrocarbon group having 5 to 16 carbon atoms, and Y is methylene, propylene, isopropylidene, isobutylidene,
Cyclohexylidene, sulfone, ketone and a single bond are selected, and R ¹ and R ² each have 2 carbon atoms.
To 6 hydrocarbon groups. ) 5. The bromine compound represented by the formula (1)
The bromine compound according to claim 4, which is a bromine compound obtained by a method of reacting an unsaturated bromine compound represented by the following formula (2) with bromine. Embedded image (Wherein, the definitions of Ar ¹ , Ar ² , Y, m and n mean the same as in the above formula (1). Q ¹ and Q ²
Represents a C2-6 hydrocarbon group having one or two identical or different unsaturated groups. ) 6. A thermoplastic resin composition comprising (B) 1 to 50 parts by weight of a bromine compound and (C) 0 to 25 parts by weight of an inorganic flame retardant aid per 100 parts by weight of a thermoplastic resin. A flame-retardant resin composition characterized in that the resin composition has an SO ₄ ^2- ion concentration of 10 ppm or less as measured by an ion chromatography method. 7. The bromine compound is obtained by performing a bromination reaction using bromine to obtain a crude solution containing a bromine compound, and then reducing the unreacted bromine remaining in the crude solution when performing a reduction treatment. 7. The flame-retardant resin composition according to claim 6, which is subjected to a reduction treatment using a sulfur compound as an agent and then recovered. 8. The flame-retardant resin composition according to claim 7, wherein the sulfur compound is sodium bisulfite, sodium dithionite, sodium sulfite, hydrogen sulfide or hydroxylamine sulfate. 9. The flame-retardant resin composition according to claim 6, wherein the bromine compound is represented by the following formula (1). Embedded image (Where m, n, p, and q are integers of 1 to 6,
Ar ¹ and Ar ² may be the same or different and are a divalent aromatic hydrocarbon group having 5 to 16 carbon atoms, and Y is methylene, propylene, isopropylidene, isobutylidene,
Cyclohexylidene, sulfone, ketone and a single bond are selected, and R ¹ and R ² each have 2 carbon atoms.
To 6 hydrocarbon groups. ) 10. The bromine compound represented by the formula (1) is a bromine compound obtained by a method of reacting an unsaturated bromine compound represented by the following formula (2) with bromine.
The flame-retardant resin composition according to the above. Embedded image (Wherein, the definitions of Ar ¹ , Ar ² , Y, m and n mean the same as in the above formula (1). Q ¹ and Q ²
Represents a C2-6 hydrocarbon group having one or two identical or different unsaturated groups. ) 11. The flame-retardant resin composition according to claim 6, wherein the thermoplastic resin is a polystyrene resin or a polyolefin resin. 12. The inorganic flame-retardant auxiliary agent is a thermoplastic resin 10
The flame-retardant resin composition according to claim 6, wherein the amount is 0.1 to 20 parts by weight based on 0 part by weight. 13. The flame retardant according to claim 6, wherein the inorganic flame retardant is at least one compound selected from the group consisting of antimony trioxide, antimony pentoxide, boron trioxide, zinc borate and red phosphorus. Resin composition. 14. A molded article formed from the resin composition according to claim 6.