Composition containing flame-retardant polyphenylene ether and method for producing the same

Abstract

The object of this invention is to provide a composition containing a flame-retardant polyphenylene ether that has a low molecular weight, excellent solubility in solvents, and high flame retardancy. [Solution] A composition comprising a flame-retardant polyphenylene ether (A) represented by the following general formula (1) is used, characterized in that the number-average molecular weight in terms of standard polystyrene, as measured by gel permeation chromatography, is 1,000 to 10,000. [Formula 1] JPEG2026066598000017.jpg28142 (In the formula, R is either absent or represents an alkylene group with 1 to 6 carbon atoms, -S-, or -SO2-, R 1 ~R 8 (Each of these independently represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, and an alkenyl group with 2 to 6 carbon atoms, while m and n are integers greater than or equal to 1.)

Description

Technical Field

[0001] The present invention relates to a composition containing polyphenylene ether excellent in flame retardancy and a method for producing the same.

Background Art

[0002] Polyphenylene ether is used as a resin material in electronic circuit board materials and the like that require low transmission loss because it has excellent dielectric properties (low dielectric constant and low dielectric tangent) in the high-frequency band. Among them, crosslinkable polyphenylene ether having a low molecular weight, excellent solubility in solvents, and functional groups capable of chemical conversion at both ends is used as a resin material. In electronic material applications, since resin materials are required to have flame retardancy, flame retardants are added to the resin. However, adding a flame retardant may impair the physical properties of the resin, so there is a demand for polyphenylene ether having a higher degree of flame retardancy.

[0003] Patent Document 1 discloses a method for producing a flame-retardant polyphenylene ether containing halogen by an oxidative co-condensation reaction of a 2,6-disubstituted phenol and a halogenated polyhydric phenol in the presence of a catalyst. However, the obtained polyphenylene ether has a bromine content that is not sufficient to contribute to flame retardancy, and when the present inventors conducted a follow-up test, the solubility in solvents was low because the molecular weight was large (see Comparative Example 1 in this specification).

[0004] Patent Document 2 discloses a method for producing a flame-retardant halogenated polyphenylene ether characterized by reacting polyphenylene ether with a halogenated phenol. However, when the present inventors conducted a follow-up test, a halogenated polyphenylene ether having a low molecular weight and a high bromine content could not be obtained (see Comparative Example 2 in this specification).

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

[0006] Conventional flame-retardant polyphenylene ethers have problems such as low solubility in solvents due to their molecular weight not being sufficiently controlled, and insufficient bromine content, which contributes to flame retardancy.

[0007] The present invention has been made in view of the above-mentioned background art, and its purpose is to provide a polyphenylene ether that has a low molecular weight, excellent solubility in solvents, and high flame retardancy. [Means for solving the problem]

[0008] As a result of diligent research, the inventors of this invention have found that the following invention can solve the above problems, and have completed this invention.

[0009] In other words, the present invention relates to the flame-retardant polyphenylene ether described below.

[0010] [1] A composition comprising a flame-retardant polyphenylene ether (A) represented by the following general formula (1), characterized in that the number-average molecular weight in terms of standard polystyrene, as measured by gel permeation chromatography, is 1,000 to 10,000.

[0011] [ka]

[0012] (In the formula, R is either absent or represents an alkylene group having 1 to 6 carbon atoms, -S-, or -SO2-, R 1 ~R 8 (Each of these independently represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, and an alkenyl group with 2 to 6 carbon atoms, while m and n are integers greater than or equal to 1.) [2] The composition according to [1], wherein the number average molecular weight is 1,000 to 5,000.

[0013] [3] The composition according to [1], further comprising a flame-retardant polyphenylene ether (B) represented by the following general formula (2).

[0014] [ka]

[0015] (In the formula, X is either absent or represents an alkylene group having 1 to 6 carbon atoms, -S-, or -SO2-, and R 9 ~R 12 Each of these independently represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, and an alkenyl group with 2 to 6 carbon atoms, where k is an integer greater than or equal to 1. [4] The composition according to [3], wherein the number average molecular weight is 1,000 to 5,000.

[0016] [5] A composition according to any one of [1] to [4], wherein the bromine content is 5% by weight or more.

[0017] [6] The composition according to [1] or [2], wherein in the general formula (1) above, R is a 2,2-propylene group and the bromine content is 5% by weight or more.

[0018] [7] The composition according to [3] or [4], wherein in the general formula (1), R is a 2,2-propylene group, and in the general formula (2), X is a 2,2-propylene group, and the bromine content is 5% by weight or more.

[0019] [8] A composition according to any one of [1] to [7], wherein the solubility in toluene at 20°C is 10% by weight or more.

[0020] [9] A method for producing the composition according to any one of [1] to [8], comprising reacting a compound represented by the following general formula (3) with a polyphenylene ether having a number average molecular weight of 5,000 to 30,000 and repeating units represented by the following general formula (4) in the presence of a radical initiator and a solvent.

[0021] [ka]

[0022] (In the formula, R is either absent or represents an alkylene group with 1 to 6 carbon atoms, -S-, or -SO2-.)

[0023] [ka]

[0024] (In the formula, R 13 ~R 16 Each of these independently represents a hydrogen atom, a C1-C6 alkyl group, or a C2-C6 alkenyl group.

[10] The manufacturing method according to [9], wherein the radical initiator is an organic peroxide.

[0025]

[11] The manufacturing method according to [9] or

[10] , wherein the solvent is one or more solvents selected from the group consisting of aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, alcohol solvents, ketone solvents and ether solvents.

[0026]

[12] The manufacturing method according to any one of [9] to

[11] , wherein the amount of compound represented by general formula (3) is 1 to 200 parts by weight per 100 parts by weight of the polyphenylene ether. [Effects of the Invention]

[0027] The composition of the present invention has the effect that, compared with conventionally known flame-retardant polyphenylene ethers, it has a low molecular weight, excellent solubility in solvents, and can ensure high flame retardancy.

Mode for Carrying Out the Invention

[0028] Hereinafter, the present invention will be described in more detail.

[0029] One aspect of the present invention relates to a composition containing a flame-retardant polyphenylene ether (A) represented by the following general formula (1).

[0030]

Chemical formula

[0031] (In the formula, R represents an alkylene group having 1 to 6 carbon atoms, -S-, or -SO2- when it exists, and R 1 ~R 8 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms, and m and n represent integers of 1 or more.) In general formula (1), the alkylene group having 1 to 6 carbon atoms represented by R is not particularly limited, and examples thereof include a methylene group, an ethylene group, a 2,2-propylene group, a 2,2-butylene group, a hexadiene group, or a 1,1-cyclohexylene group.

[0032] In general formula (1), R is preferably an alkylene group having 1 to 3 carbon atoms, and more preferably a 2,2-propylene group, in terms of excellent heat resistance and the like.

[0033] In general formula (1), R 1 ~R 8 The alkyl group having 1 to 6 carbon atoms represented by is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, etc. Among them, a methyl group is preferred.

[0034] In general formula (1), R 1 ~R 8 The alkenyl group having 2 to 6 carbon atoms represented by is not particularly limited, but examples include vinyl group, allyl group, iso-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 1-hexenyl group, etc. In general formula (1), m and n represent the average number of repetitions of the repeating unit of the flame-retardant polyphenylene ether, and in the present invention, m and n represent integers of 1 or more.

[0035] For example, if R is a 2,2-propylene group, 1 , R 2 , R 5 , R 6 is a methyl group, R 3 , R 4 , R 7 , R 8 When is a hydrogen atom and both m and n are 10, the theoretical average molecular weight of the flame-retardant polyphenylene ether (A) of the present invention is 2,947. One embodiment of the flame-retardant polyphenylene ether (A) represented by general formula (1) is, for example, a compound having the structure shown in formula (5).

[0036] [ka]

[0037] (In the formula, R is either absent, represents an alkylene group with 1 to 6 carbon atoms, -S-, or -SO2-, and m and n represent integers of 1 or greater.) Furthermore, one aspect of the present invention relates to a composition further comprising a flame-retardant polyphenylene ether (B) represented by the following general formula (2).

[0038] [ka]

[0039] (In the formula, X is either absent or represents an alkylene group having 1 to 6 carbon atoms, -S-, or -SO2-, and R 9 ~R 12 Each of these independently represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, and an alkenyl group with 2 to 6 carbon atoms, where k is an integer greater than or equal to 1. In general formula (2), the alkylene group having 1 to 6 carbon atoms represented by X is not particularly limited, but examples include a methylene group, an ethylene group, a 2,2-propylene group, a 2,2-butylene group, a hexadiene group, or a 1,1-cyclohexylene group.

[0040] In general formula (2), X is preferably an alkylene group having 1 to 3 carbon atoms, and more preferably a 2,2-propylene group, due to its excellent heat resistance and other properties.

[0041] In general formula (2), R 9 ~R 12 The alkyl group having 1 to 6 carbon atoms represented by is not particularly limited, but examples include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc., with methyl group being preferred among them.

[0042] In general formula (2), R 9 ~R 12 The alkenyl group having 2 to 6 carbon atoms represented by is not particularly limited, but examples include vinyl group, allyl group, iso-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 1-hexenyl group, etc. In general formula (2), k represents the average number of repetitions of the repeating unit of the flame-retardant polyphenylene ether (B), and in the present invention, k represents an integer of 1 or more.

[0043] For example, if X is a 2,2-propylene group, R 9 , R 10 is a methyl group, R 11 , R 12When is a hydrogen atom and k is 20, the theoretical average molecular weight of the flame-retardant polyphenylene ether (B) of the present invention is 2,947.

[0044] One embodiment of the flame-retardant polyphenylene ether (B) represented by general formula (2) is, for example, a compound having the structure shown in formula (6).

[0045] [ka]

[0046] (In the formula, X is either absent, represents an alkylene group with 1 to 6 carbon atoms, -S-, or -SO2-, and n is an integer greater than or equal to 1.) The composition of the present invention has excellent solubility in solvents, and preferably has a number-average molecular weight in terms of standard polystyrene, measured by gel permeation chromatography, of 1,000 to 10,000, more preferably 1,000 to 8,000, and even more preferably 1,000 to 5,000.

[0047] The composition of the present invention exhibits excellent solubility in solvents, and its weight-average molecular weight (M) is measured in terms of standard polystyrene by gel permeation chromatography. w ) and number-average molecular weight (M n ) ratio (M w / M n The value of ) is preferably 1.0 to 4.0, more preferably 1.2 to 3.0, and even more preferably 1.5 to 2.5.

[0048] In the composition of the present invention, a bromine content of 5 to 30% by weight is preferred, and more preferably 7 to 20% by weight, in order to obtain high flame retardancy.

[0049] The compositions of the present invention are not particularly limited, but as an example, they can be produced by reacting a compound represented by the following general formula (3) with a polyphenylene ether having a number average molecular weight of 5,000 to 30,000 and repeating units represented by the following general formula (4) in the presence of a radical initiator and a solvent.

[0050] [ka]

[0051] (In the formula, R is either absent or represents an alkylene group with 1 to 6 carbon atoms, -S-, or -SO2-.)

[0052] [ka]

[0053] (In the formula, R 13 ~R 16 Each of these independently represents a hydrogen atom, a C1-C6 alkyl group, or a C2-C6 alkenyl group. The compound represented by general formula (3) is not particularly limited, but examples include tetrabromobisphenol A, tetrabromobisphenol F, or bis(4'-hydroxy-3',5'-dibromophenyl)sulfone. Of these, tetrabromobisphenol A is particularly preferred due to its excellent heat resistance and dielectric properties.

[0054] In a polyphenylene ether having repeating units represented by general formula (4), R 13 ~R 16 The alkyl group having 1 to 6 carbon atoms represented by is not particularly limited, but examples include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc., with methyl group being preferred among them.

[0055] In a polyphenylene ether having repeating units represented by general formula (4), R 13 ~R 16 The alkenyl group having 2 to 6 carbon atoms represented by is not particularly limited, but examples include vinyl group, allyl group, iso-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 1-hexenyl group, etc.

[0056] One embodiment of a polyphenylene ether having repeating units represented by general formula (4) is, for example, a compound having repeating units represented by formula (7).

[0057] [ka]

[0058] In polyphenylene ethers having repeating units represented by general formula (4), the number-average molecular weight in terms of standard polystyrene, as measured by gel permeation chromatography, is preferably 5,000 to 30,000, and more preferably 5,000 to 20,000.

[0059] In the production of the composition of the present invention, the radical initiator is not particularly limited, but examples include peroxides (especially organic peroxides). Specifically, examples include dibenzoyl peroxide, di(3-methylbenzoyl) peroxide, benzoyl(3-methylbenzoyl) peroxide, and 2,5-dimethyl-2,5-di(benzoylperoxy)hexane. Among these, dibenzoyl peroxide is preferred because it yields a flame-retardant polyphenylene ether with a low molecular weight and a high bromine content.

[0060] In the production of the composition of the present invention, the solvent is not particularly limited as long as it does not react with the substrate, but examples include aromatic hydrocarbon solvents such as benzene, toluene, and xylene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and 1,1,2,2-tetrachloroethane; alcoholic solvents such as methanol, ethanol, n-propanol, iso-propanol, and butanol; ketone solvents such as acetone, methyl ethyl ketone, diethyl ketone, methyl butyl ketone, and methyl isobutyl ketone; and etheric solvents such as tetrahydrofuran and dioxane. These solvents may be used individually or in combination of two or more. In the production of the composition of the present invention, the reaction temperature is not particularly limited, but is preferably in the range of 40°C to 160°C, and more preferably in the range of 50°C to 150°C.

[0061] In the production of the composition of the present invention, the mixing ratio of the compound represented by general formula (3) and the compound represented by general formula (4) is preferably 1 to 200 parts by weight, more preferably 5 to 150 parts by weight, and even more preferably 10 to 100 parts by weight of the compound represented by general formula (3) per 100 parts by weight of the compound represented by general formula (4).

[0062] In the production of the composition of the present invention, the amount of radical initiator used is preferably 0.1 to 100 parts by weight, more preferably 1 to 80 parts by weight, and more preferably 2 to 50 parts by weight, per 100 parts by weight of the compound represented by the general formula (4) above.

[0063] In the production of the composition of the present invention, the amount of solvent used is preferably 100 to 2,000 parts by weight, more preferably 150 to 1,500 parts by weight, and even more preferably 200 to 1,000 parts by weight, per 100 parts by weight of the compound represented by the general formula (4) above.

[0064] In the production of the composition of the present invention, after the reaction is complete, the obtained composition is recovered by any method and, if necessary, subjected to post-treatment such as washing. Known methods such as concentration and reprecipitation can be used to recover the polymer from the reaction solution. [Examples]

[0065] The present invention will be described in more detail below based on examples, but the present invention is not limited in any way to these examples. Number-average molecular weight (M) determined by gel permeation chromatography (GPC) n ) and weight-average molecular weight (M w ) measurement> Equipment: Tosoh HLC-8320GPC Columns: Connect TSKgel SuperAW2500, SuperAW3000, and SuperAW5000 manufactured by Tosoh Corporation. Eluent: Tetrahydrofuran Flow rate: 0.6mL / min Column temperature: 40℃ Detector: UV (254nm) Calibration curve: A calibration curve was obtained using the following standard substances (all standard polystyrene manufactured by Tosoh). ·"A-500" (weight average molecular weight = 589) ·"A-1000" (weight average molecular weight = 1,120) ·"A-2500" (weight average molecular weight = 3,120) ·"A-5000" (weight average molecular weight = 5,520) ·"F-1" (weight average molecular weight = 8,840) ·"F-2" (weight average molecular weight = 15,700) ·"F-4" (weight average molecular weight = 37,200) ·"F-10" (weight average molecular weight = 110,000) ·"F-20" (weight average molecular weight = 225,000) <Measurement of bromine content by combustion-ion chromatography> Combustion device: Mitsubishi Chemical Analytech AQF-2100H Sample quantity: 4 mg Combustion temperature: 900 °C on the inlet side and 1000 °C on the outlet side Absorbent composition: 30 mg / L hydrogen peroxide solution Absorbent volume: 30 mL Ion chromatograph: IC-2010 manufactured by Tosoh Corporation Eluent: 7.5 mmol / L aqueous sodium hydrogen carbonate solution + 0.8 mmol / L aqueous sodium carbonate solution Detection: Conductivity Analytical column: TSKgel SuperIC-Anion HS Guard column: TSKguardcolumn SuperIC-A HS Column temperature: 40 °C Injection volume: 30 μL Flow rate: 1.5 mL / min Suppressor gel: TSKgel suppress IC-A <Structural analysis by NMR> Apparatus: JNM-EC 400YH manufactured by JEOL Ltd. Solvent: 1,1,2,2-tetrachloroethane-d2 In the flame-retardant polyphenylene ether (A) represented by the general formula (1), the hydrogen on the brominated aromatic ring 1 The 1H NMR peak is observed around 6.99 ppm. Further, in the flame-retardant polyphenylene ether (B) represented by the general formula (2), the hydrogen on the brominated aromatic ring 1 The 1H NMR peak is observed around 7.42 ppm and around 7.29 ppm. Based on the integral values of these 1 1H NMR peaks, the ratio of the flame-retardant polyphenylene ether (A) to the flame-retardant polyphenylene ether (B) was calculated as the oligomer ratio. <Measurement of glass transition temperature by differential scanning calorimetry (DSC)> Apparatus: DSC 200 F3 manufactured by Netzsch Measurement conditions: Under a nitrogen atmosphere, the temperature was raised to 240 °C at a rate of 10 °C / min, then lowered to 25 °C at a rate of 40 °C / min, and then raised to 240 °C at a rate of 10 °C / min to measure the glass transition temperature (T g ). <Evaluation of solubility in toluene> 0.10 g of flame-retardant polyphenylene ether and 0.90 g of toluene (10% by weight) were placed in a 9 mL glass screw-top tube and mixed for 30 minutes at 20°C using a stirring bar and a magnetic stirrer. After standing for 24 hours, the solution was judged as "○" if it remained transparent, and as "×" if it became opaque or if the presence of insoluble matter was detected. <Synthesis of flame-retardant polyphenylene ether> Example 1 In a 50 mL three-necked round-bottom flask equipped with a magnetic stirring bar and reflux condenser, add 25 g of toluene (manufactured by Kishida Chemical Co., Ltd.) and 5.00 g of poly(2,6-dimethyl-1,4-phenylene ether) (manufactured by BLD Pharmatech, M n (=17,000), 2.50 g of tetrabromobisphenol A (Tosoh Corporation, 7.35 mmol) was added, and the mixture was heated to 90°C while stirring. At this temperature, a solution of 1.00 g of dibenzoyl peroxide (Tokyo Chemical Industries Corporation, approximately 25% water-wet product, 3.10 mmol) dissolved in 5 g of toluene was added dropwise over 30 minutes. After the addition was complete, the mixture was stirred at 90°C for 3 hours and then allowed to cool to room temperature. The resulting reaction mixture was added to methanol (Kishida Chemical Co., Ltd.), the precipitated solid was filtered, washed with methanol, and then dried. A composition (a) containing a white solid flame-retardant polyphenylene ether was obtained in 68% yield.

[0066] The analysis results of the product are shown below. 1 H NMR (400MHz, tetrachloroethane-d2, ppm) δ=7.42(Ar-H),7.29(Ar-H),6.99(Ar-H),6.56-6.36(Ar-H),2.25-1.95(C H 3), 1.66-1.59(C H 3) M n =2,900,M w =5,700, M w / M n =2.0 Bromine content = 5.7% by weight Oligomer ratio = 7:3 Example 2 In Example 1, the same procedure was followed except that the amount of tetrabromobisphenol A used was 3.00 g, and a composition (b) containing a white solid flame-retardant polyphenylene ether was obtained in a yield of 68%.

[0067] The analysis results of the product are shown below. 1 H NMR (400MHz, tetrachloroethane-d2, ppm) δ=7.42(Ar-H),7.29(Ar-H),6.99(Ar-H),6.56-6.36(Ar-H),2.21-1.95(C H 3), 1.66-1.59(C H 3) M n =2,300,M w =5,600, M w / M n =2.0 Bromine content = 7.1% by weight Oligomer ratio = 6:4 Example 3 In Example 1, the same procedure was followed except that the amount of tetrabromobisphenol A used was 4.00 g, and a composition (c) containing a white solid flame-retardant polyphenylene ether was obtained in a yield of 56%.

[0068] The analysis results of the product are shown below. 1 H NMR (400MHz, tetrachloroethane-d2, ppm) δ=7.42(Ar-H),7.29(Ar-H),6.99(Ar-H),6.56-6.36(Ar-H),2.21-1.95(C H 3), 1.66-1.62(C H 3) M n =2,800,M w =4,900,M w / M n = 1.8 Bromine content = 7.4% by weight T g = 155℃ Oligomer ratio = 5:5 Example 4 In Example 1, the same procedure was followed except that the amount of tetrabromobisphenol A used was 5.00 g, and a composition (b) containing a white solid flame-retardant polyphenylene ether was obtained in a yield of 52%.

[0069] The analysis results of the product are shown below. 1 H NMR (400MHz, tetrachloroethane-d2, ppm) δ=7.42(Ar-H),7.29(Ar-H),6.99(Ar-H),6.56-6.36(Ar-H),2.21-1.95(C H 3), 1.66-1.59(C H 3) M n =2,600,M w =5,000, M w / M n =1.9 Bromine content = 8.7% by weight Oligomer ratio = 4:6 Example 5 In Example 1, the same procedure as in Example 2 was carried out, except that the amount of dibenzoyl peroxide used was 0.50 g and the amount of tetrabromobisphenol A used was 3.00 g, and a composition (d) containing a white solid flame-retardant polyphenylene ether was obtained in a yield of 62%.

[0070] The analysis results of the product are shown below. 1 H NMR (400MHz, tetrachloroethane-d2, ppm) δ=7.42(Ar-H),7.29(Ar-H),6.99(Ar-H),6.56-6.36(Ar-H),2.25-1.95(C H 3), 1.66-1.62(C H 3) M n =3,600, M w =6,300,M w / M n = 1.8 Bromine content = 7.1% by weight Oligomer ratio = 5:5 Comparative Example 1 Polyphenylene ethers were synthesized according to the method of Example 1 described in Patent Document 1 (Japanese Unexamined Patent Publication No. 51-600), and a brown solid product (D) was obtained in a yield of 91%.

[0071] The analysis results of the product are shown below. M n =27,000,M w =51,000,M w / M n =1.9 Bromine content = 4.9% by weight T g =200℃ Comparative Example 2 Polyphenylene ethers were synthesized according to the method of Example 4 described in Japanese Patent Publication No. 51-8398, and a white solid product (E) was obtained in a yield of 70%.

[0072] The analysis results of the product are shown below. M n =16,000,M w =39,000,M w / M n =2.4 Bromine content = 0.8% by weight The results obtained are shown in Table 1.

[0073] [Table 1]

[0074] From the above results, it can be seen that the flame-retardant polyphenylene ether of the present invention has a lower molecular weight, excellent solubility in solvents, and a higher bromine content compared to conventional polyphenylene ethers.

Claims

1. A composition comprising a flame-retardant polyphenylene ether (A) represented by the following general formula (1), characterized in that the number-average molecular weight in terms of standard polystyrene, as measured by gel permeation chromatography, is 1,000 to 10,000. 【Chemistry 1】 (In the formula, R is either absent, an alkylene group having 1 to 6 carbon atoms, -S-, or -SO) ２ - indicates R １ ~R ８ Each of these independently represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, and an alkenyl group with 2 to 6 carbon atoms, where m and n are integers of 1 or greater.

2. The composition according to claim 1, wherein the number average molecular weight is 1,000 to 5,000.

3. The composition according to claim 1, further comprising a flame-retardant polyphenylene ether (B) represented by the following general formula (2). 【Chemistry 2】 (In the formula, X is either absent, an alkylene group having 1 to 6 carbon atoms, -S-, or -SO) ２ - indicates R ９ ~R １２ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms, and k is an integer greater than or equal to 1.

4. The composition according to claim 3, wherein the number average molecular weight is 1,000 to 5,000.

5. The composition according to any one of claims 1 to 4, wherein the bromine content is 5% by weight or more.

6. The composition according to claim 1 or claim 2, wherein in the general formula (1), R is a 2,2-propylene group and the bromine content is 5% by weight or more.

7. The composition according to claim 3 or claim 4, wherein in the general formula (1), R is a 2,2-propylene group, and in the general formula (2), X is a 2,2-propylene group, and the bromine content is 5% by weight or more.

8. The composition according to any one of claims 1 to 4, wherein the solubility in toluene at 20°C is 10% by weight or more.

9. A method for producing the composition according to any one of claims 1 to 4, comprising reacting a compound represented by the following general formula (3) with a polyphenylene ether having repeating units represented by the following general formula (4) and a number-average molecular weight of 5,000 to 30,000, in the presence of a radical initiator and a solvent. 【Transformation 3】 (In the formula, R is either absent, an alkylene group having 1 to 6 carbon atoms, -S-, or -SO) ２ (This indicates -.) 【Chemistry 4】 (wherein, R １３ ~R １６ each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms.)

10. The manufacturing method according to claim 9, wherein the radical initiator is an organic peroxide.

11. The manufacturing method according to claim 9 or claim 10, wherein the solvent is one or more solvents selected from the group consisting of aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, alcohol solvents, ketone solvents, and ether solvents.

12. The manufacturing method according to claim 9 or claim 10, wherein the compound represented by the general formula (3) is 1 to 200 parts by weight per 100 parts by weight of the polyphenylene ether.

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