JPH09301905A - Brominated p-cumylphenol and its derivative, their production and flame-retardant resin composition blended with the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound excellent in light resistance and processability (flowability) when blended in a resin and useful as a flame- retardant for compounding flame-retardant resins frequently used in various electric instruments, etc. SOLUTION: This brominated p-cumylphenol expressed by formula I [(a) is 1-3 integer; (b) is 1-2 integer] is obtained by brominating p-cumylphenol with a brominating agent (e.g. bromine chloride) in the presence of a catalyst (e.g. aluminum chloride). The compound of formula I preferably has 2.5-4.0 average brominated number, contains 45-62wt.% bromine, is a viscous material at room temperature having pale yellow color, liquid at >=50 deg.C and contains 0.001-30wt.% of dibromo derivative, 30-95wt.% of tribromo derivative, 1-65wt.% of tetrabromo derivative and 0.01-10wt.% of pentabromo derivative. It is preferable to blend 5-50 pts.wt. of the compound of formula I with 100 pts.wt. of a resin.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel brominated p-cumylphenol and its derivatives. The compound of the present invention can be used as a compounded flame retardant for a flame retardant resin, which is frequently used in various electric devices.

[0002]

2. Description of the Related Art As conventional flame retardants for synthetic resins, various brominated flame retardants, phosphoric acid ester flame retardants, inorganic flame retardants, etc. are used for various resins. Has been done. Typical flame retardants include decabromodiphenyl oxide, tetrabromobisphenol-A (hereinafter abbreviated as TBA), TBA-epoxy oligomer, magnesium hydroxide, aluminum hydroxide and the like.

[0003]

As described above, although various flame retardants have been proposed and used properly for various purposes, the recent regulations for flame retardancy have been strengthened and the performance of blended flame retardant resins has been further improved. There is a strong demand for improvement, and the creation of agents that complement the drawbacks of conventional products is desired.

[0004]

Means for Solving the Problems As a result of extensive studies on a novel bromine-based agent, the present inventors have found a brominated p-cumylphenol and a brominated p-cumylphenol derivative obtained therefrom. Furthermore, when these agents are blended with a resin, they find that they are remarkably excellent in processability (flowability), and in addition, they find that the brominated p-cumylphenol derivative of the present invention is excellent in light resistance. The present invention has been completed.

That is, the present invention provides the following general formula (1)

[0006]

Embedded image

Brominated p-cumylphenol represented by the formula (a is an integer of 1 to 3 and b is an integer of 1 to 2) and the following general formula (2)

[0008]

[Chemical 6]

(Wherein a is an integer of 1 to 3, b is an integer of 1 to 2, and n is an integer of 1 or more) or the following general formula (3).

[0010]

[Chemical 7]

(In the formula, a is an integer of 1 to 3, b is an integer of 1 to 2, and n is an integer of 1 or more.)
A cumylphenol derivative, a method for producing them, and a flame-retardant resin composition obtained by mixing them.

Hereinafter, the present invention will be described in detail.

The brominated p-cumylphenol of the present invention is
It has a structure represented by the general formula (1), and its typical physical properties are as follows.

(1) Bromination p obtained by bromination reaction
-The average bromination number of cumylphenol is 2.5-4.0.
And the bromine content in the product is 45-62.
% By weight.

(2) The shape of the product is a viscous substance which is slightly yellowish at room temperature, and is in a solution state at 50 ° C. or higher.

The average bromination number in the present invention means the average bromination number per molecule calculated based on the composition ratio obtained by elemental analysis of brominated p-cumylphenol.

(3) As a result of gas chromatography analysis, the product is 0.001 to 30% by weight of dibromo compound, 30 to 99% by weight of tribromo compound, and 1 to 1% of tetrabromo compound.
80% by weight and 0.01 to 10% by weight of pentabromo compound, more preferably 0.001 to 30% by weight of dibromo compound, 30 to 95% by weight of tribromo compound, and 1 to 1 of tetrabromo compound. 65 wt% and pentabromo compound in the range of 0.01 to 10 wt%.

Next, a method for obtaining the brominated p-cumylphenol of the present invention will be described.

As the method for preparing the brominated p-cumylphenol of the present invention, for example, the starting material p-cumylphenol is dissolved in a solvent inert to the reaction in the presence of a catalyst, and the brominated reagent is added dropwise thereto. Then react.

Examples of the catalyst applicable to the present invention include aluminum chloride, aluminum bromide, ferric chloride, ferric bromide, titanium tetrachloride, titanium trichloride, antimony pentachloride, antimony trichloride, and trichloride. Examples include Lewis acid catalysts such as antimony bromide, tin chloride, and trifluoroborane etherate. These catalysts are selected according to the desired bromination number. Moreover, even if these catalysts are used alone or as a mixture of two or more kinds, there is no problem.

The catalyst may be added in any amount with respect to the raw material p-cumylphenol used for the reaction, and specifically, it may be added to 1 mol of the raw material p-cumylphenol. It is in the range of 001 to 100 mol%. With a small amount of addition, the reaction may be slow or impurities due to the raw materials and the solvent may deactivate the catalyst, while an excessive addition is not economical. Therefore, preferably 0.1 to
It is in the range of 40 mol%.

The bromination reagent applicable to the present invention is not particularly limited, but specific examples thereof include bromine and bromine chloride. Of these, it is more preferable to use bromine chloride. The addition amount of bromine or bromine chloride is changed depending on the average bromination number of the target brominated p-cumylphenol. Usually, it is used in an equimolar amount to 5 molar amount or less with respect to the target average bromination number, but preferably in an equimolar amount to 1.5 molar amount range, The amount of brominating agent used is determined depending on the type and reaction conditions. When bromine chloride is used, the mixing ratio of bromine and chlorine used for the preparation is 0.5 to 0.5 mol of chlorine for 1 mol of bromine.
Used in the range of 1.0 molar ratio. This is to reduce the content of the chlorinated product in the product, and when chlorine is used in an equimolar ratio or more, a large amount of the chlorinated product is by-produced, which is not preferable.

As the solvent used in the reaction, any solvent can be applied as long as it is inert to the bromination reagent and the catalyst and can be azeotropically distilled with water. Specifically, dichloromethane, dibromo Methane, chloroform,
Bromoform, carbon tetrachloride, 1,2-dichloroethane,
Examples are 1,1,2-trichloroethane and the like.

The solvent can be used in any ratio with respect to the raw material p-cumylphenol used in the reaction, but if the amount is 1 weight or less, the viscosity of the reaction solution after the reaction is high. Therefore, it is not preferable, and if the amount is 100 weight times or more, it is not economical. Therefore, preferably 2 to 5
The range is 0 weight times.

The reaction temperature varies depending on the bromination reagent, the catalyst and the desired average bromination degree. Generally, when bromine is used, it is in the range of 0 ° C to 60 ° C, when bromine chloride is used, or when bromine chloride is used. -30 ℃ when using bromine chloride together
It is carried out in the range of -20 ° C. The drip time of the brominated reagent is
Since this reaction is an exothermic reaction, it is not particularly limited as long as the reaction temperature can be controlled.

Post-treatment may be carried out immediately after the addition of the bromination reagent, or aging may be carried out at a predetermined temperature for 1 to 8 hours.

After completion of the reaction, excess brominated reagent is removed by adding a reducing agent such as hydrazine and sodium bisulfite, and then washed with water to obtain a solution containing brominated p-cumylphenol. .

Recovery of brominated p-cumylphenol from this solution can be carried out by introducing steam into this solution. First, the contained solvent is distilled off, and then the low boiling point substance which is an impurity by-produced in the bromination reaction is distilled off. After the distillation, the organic phase in the solution state is separated under heating and cooled to room temperature to recover the viscous brominated p-cumylphenol.

As a method for removing the low boiling point substances, thin film distillation or the like may be used.

Next, the brominated p-cumylphenol derivative of the present invention represented by the above general formula (2) or general formula (3) and the method for producing them will be described.

The brominated p-cumylphenol derivative of the present invention has a bromine content of 40 to 62% and a softening point of 80 to 200 ° C.
It is a compound that exhibits a heat resistance of 5% weight loss temperature of 300 ° C. or more by a thermobalance and is superior in light resistance to other commercial agents.

The brominated p-cumylphenol derivative of the present invention can be produced by using the brominated p-cumylphenol represented by the above general formula (1) and the following general formula (4).

[0033]

Embedded image

It can be obtained by reacting a compound having an epoxy group at the molecular end represented by the formula (wherein m represents an integer of 0 or more) at 80 to 210 ° C. in the presence of a catalyst.

The amount of brominated p-cumylphenol used in the production of the brominated p-cumylphenol derivative of the present invention is such that the compound having an epoxy group at the molecular end is used.
It can be used in a ratio of 0.5 to 2.0 mol / mole, and a more preferable ratio for a flame retardant is 0.9 to 2.0 mol / mole.
It is a range of molar ratio.

Specific examples of the catalyst used for producing the brominated p-cumylphenol derivative of the present invention include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and triphenylbenzylphosphonium chloride. , Triphenylethylphosphonium bromide,
Butyltriphenylphosphonium chloride, octyltriphenylphosphonium bromide, tetraphenylphosphonium chloride, salts of quaternary phosphorus compounds such as triphenylmethylphosphonium iodide, tetramethylammonium chloride, tetramethylammonium bromide , Tetraethylammonium chloride, tetraethylammonium bromide, tetra n-butylammonium chloride, tetra n-butylammonium bromide, trimethylphenylammonium chloride, trimethylphenylammonium bromide, triethylphenylammonium chloride, triethylphenylammonium bromide, trimethylbenzylammonium chloride, triethylbenzyl Ammo Quaternary ammonium salts such as Um bromide are exemplified.

The amount of the catalyst added is not particularly limited, but is usually 0.01 to 20 mol% relative to the brominated p-cumylphenol of the above general formula (1).

The reaction temperature is usually in the range of 80 to 210 ° C., though it depends on the kind of the catalyst. However, when the reaction is carried out in a solvent-free system, the raw material and the product are melted under stirring conditions. carry out. In addition, if necessary, ketones such as methyl ethyl ketone and methyl isobutyl ketone, toluene,
Aromatic hydrocarbons such as xylene and mesitylene may be used as a solvent.

When the reaction is carried out without a solvent, after the reaction,
The desired product is obtained by cooling and solidifying, and if necessary, crushing and crushing treatment is performed. When the reaction is carried out using a solvent, the target product is obtained by the same procedure as in the case of no solvent after the solvent is distilled off.

The brominated p-cumylphenol and the brominated p-cumylphenol derivative of the present invention are used as flame retardants.

The flame-retardant resin composition of the present invention comprises a thermosetting resin or a thermoplastic resin, the brominated p-cumylphenol or the brominated p-cumylphenol derivative of the present invention, a flame retardant aid, and the like. Further, if necessary, additives may be added to an ultraviolet absorber, a light stabilizer, an antioxidant, an antistatic agent, an inorganic filler and the like.

Specific examples of resins that can be blended with the brominated p-cumylphenol and the brominated p-cumylphenol derivative of the present invention include phenol resins, urea resins, melamine resins, unsaturated polyester resins, Thermosetting resins such as polyurethane, alkyd resin, epoxy resin, low density polyethylene, high density polyethylene, ethylene-vinyl acetate copolymer, polystyrene, high impact polystyrene, expanded polystyrene, acrylonitrile-styrene copolymer, Chloronitrile-styrene-butadiene copolymer (abbreviated as ABS hereinafter), polypropylene, petroleum resin, polymethylmethacrylate, polyamide, polycarbonate, polyethylene terephthalate,
Examples thereof include thermoplastic resins such as polybutylene terephthalate and polyphenylene ether. Polymer alloys typified by polycarbonate-ABS and polyphenylene ether-polystyrene in which two or more thermoplastic resins are mixed can also be exemplified. Among these, low density polyethylene, high density polyethylene, ethylene-vinyl acetate copolymer, polystyrene, impact-resistant polystyrene, expanded polystyrene, acrylonitrile-styrene copolymer,
Achloronitrile-styrene-butadiene copolymer (hereinafter abbreviated as ABS), polypropylene, petroleum resin, polymethylmethacrylate, polyamide, polycarbonate,
Examples of suitable resins include thermoplastic resins such as polyethylene terephthalate, polybutylene terephthalate, and polyphenylene ether. Polymer alloys typified by polycarbonate-ABS and polyphenylene ether-polystyrene, which are a mixture of two or more thermoplastic resins, are also suitable. It is illustrated.

The blending amount of the brominated p-cumylphenol and the brominated p-cumylphenol derivative of the present invention to the resin varies depending on the type of the blended resin and the intended flame retardant performance, and is particularly limited. Not usually, but resin 10
5 to 50 parts by weight is blended with 0 parts by weight.

When blending the brominated p-cumylphenol and the brominated p-cumylphenol derivative of the present invention with a resin, a flame retardant aid such as antimony trioxide or sodium antimonate may be added. In this case, 5 to 80 parts by weight is usually added to 100 parts by weight of the brominated polystyrene of the present invention. Further, if necessary, a benzotriazole-based ultraviolet absorber, a light stabilizer of a 2,2,6,6-tetramethylpiperidine derivative, a hindered phenol-based antioxidant, etc. may be added. In this case, Usually, 0.05 to 5 parts by weight is added to 100 parts by weight of the flame-retardant resin composition of the present invention. In addition to these, an antistatic agent or an inorganic filler such as talc or glass fiber may be added if necessary.

As a method of blending the brominated p-cumylphenol and the brominated p-cumylphenol derivative of the present invention with a resin, when blended with a thermosetting resin, for example,
The brominated polystyrene of the present invention may be previously dispersed in a resin raw material and then cured, and when blended in a thermoplastic resin, for example, a conical blender or a tumbler mixer is used to mix the necessary blending reagents, It may be pelletized using a shaft extruder or the like. The method for processing the flame-retardant resin composition obtained by these methods is not particularly limited, and for example, extrusion molding, injection molding or the like can be performed to obtain the target molded product.

[0046]

INDUSTRIAL APPLICABILITY The brominated p-cumylphenol and the brominated p-cumylphenol derivative of the present invention are useful flame retardants, especially when blended with thermosetting resins and thermoplastic resins High flame retardant performance can be exhibited without deteriorating the physical properties.

[0047]

EXAMPLES The present invention will be described below in more detail with reference to examples, but the present invention is not limited to these examples.

Example 1 p-cumylphenol 4 was added to a 1 liter four neck round bottom flask equipped with a stirrer and a dropping funnel equipped with a cooling jacket.
2.4 g (0.2 mol), 2.1 g of antimony trichloride
(0.01 mol) and methylene chloride (382 g) were charged,
It cooled at -2 degreeC using the cooling circulation thermostat.

Next, 69.9 g (0.44 mol) of bromine and 379 g of methylene chloride were charged into a 0.5-liter four-necked round bottom flask, and after cooling to 0 ° C. by a cooling constant temperature circulation device, chlorine 24. 8 g (0.35 mol) was blown in over 1 hour to prepare a methylene chloride solution of bromine chloride.
This methylene chloride solution of bromine chloride was charged into the dropping funnel equipped with the cooling jacket, dropped into the p-cumylphenol solution over 6 hours, and aged for 30 minutes.

After the reaction, a 5 wt% hydrazine solution was added to the reaction solution to remove residual bromine chloride and excess bromine, followed by liquid separation and washing with water to obtain a p-cumylphenol solution. .

Steam was blown into the brominated p-cumylphenol solution to distill away the solvent, and then the low boiling impurities were similarly distilled off. After steam distillation, the solution layer of brominated p-cumylphenol was separated while maintaining the temperature. Then, this solution was dried under reduced pressure at 90 ° C. to obtain 87.3 g of brominated p-cumylphenol in a slightly yellowish viscous state. The results of elemental analysis, nuclear magnetic resonance spectrum, gas chromatography and infrared absorption spectrum of the obtained p-cumylphenol are shown below.

(1) Elemental analysis result C H Br Cl measured value (% by weight) 38.9 2.9 53.3 1.4 The average bromination number per molecule calculated from this elemental analysis result was 3.1. Met. (2) Nuclear magnetic resonance spectrum (CDCl ₃ , H1, pp
m): δ 1.4 to 1.8 (m, 6H), 5.7 to 5.8.
(S, 1H), 6.9 to 7.6 (m, 5.9H) (3) Gas chromatography (DB-1, 0.25m)
m.times.15 m): dibromo compound; 0.01 wt%, dibromomonochloro compound; 2.27 wt%, tribromo compound; 92.
49 wt%, tetrabromo compound; 4.93 wt%, pentabromo compound; 0.01 wt%, low boiling point substance: 0.29 wt% (4) Infrared absorption spectrum (KBr, cm ^-1 ): 349
5,2970,1763,1648,1589,155
9, 1475, 1396, 1364, 1320, 127
1,1246,1200,1170,1141,109
2,1009,930,876,863,825,78
8,737,716.

Example 2 p-cumylphenol 4 was added to a 1 liter four neck round bottom flask equipped with a stirrer and a dropping funnel equipped with a cooling jacket.
2.4 g (0.2 mol), 2.1 g of antimony trichloride
(0.01 mol) and methylene chloride (382 g) were charged,
It cooled at -2 degreeC using the cooling circulation thermostat.

Next, 89.5 g (0.56 mol) of bromine and 486 g of methylene chloride were charged into a 0.5-liter four-necked round bottom flask, and the mixture was cooled to 0 ° C. by a cooling constant temperature circulation device, and then chlorine 31. 9 g (0.45 mol) was blown in over 1 hour to prepare a methylene chloride solution of bromine chloride.
This methylene chloride solution of bromine chloride was charged into the dropping funnel equipped with the cooling jacket, dropped into the p-cumylphenol solution over 12 hours, and aged for 30 minutes.

After the reaction, a 5 wt% hydrazine solution was added to the reaction solution to remove residual bromine chloride and excess bromine, followed by liquid separation and washing with water to obtain a p-cumylphenol solution. ..

Water vapor was blown into the solution of brominated p-cumylphenol to distill away the solvent, and then the low boiling point impurities were similarly distilled off. After steam distillation, the solution layer of brominated p-cumylphenol was separated while maintaining the temperature. Then, this solution was dried under reduced pressure at 90 ° C. to obtain 98.7 g of brominated p-cumylphenol in a slightly yellowish viscous state. The obtained p-cumylphenol was measured by gas chromatography. As a result, dibromo compound: 0.10 wt%, dibromomonochloro compound: 1.91 wt%, tribromo compound: 17.49 w
t%, tetrabromo compound; 77.93 wt%, pentabromo compound; 1.76 wt%, and low-boiling substance; 0.90 wt%
Met. The average bromination number calculated from the results of elemental analysis was 3.8.

Example 3 10 parts by weight of the brominated p-cumylphenol obtained in Example 1 was added to 100 parts by weight of high impact polystyrene (hereinafter abbreviated as HIPS; HT-88 manufactured by Mitsubishi Chemical). 3.3 parts by weight of antimony trioxide were mixed and roll kneading was performed at 200 ° C. Subsequently, after press molding at 200 ° C., a sample piece for evaluation was prepared, and the obtained sample piece was
The flammability test and the fluidity (MFR) were measured by the following methods.

(1) Flammability test The obtained sample pieces were evaluated for flammability according to the oxygen index measurement method and UL94V vertical flammability test method specified in JIS K7201.

(2) Fluidity (MFR) The obtained sample piece was subjected to a fluidity (MFR) measurement method (measurement temperature; 200 ° C., standardized in JIS K 7210).
(Weight: 5 kg). The results are shown in Table 1.

[0060]

[Table 1]

Examples 4 to 5 Test pieces were prepared by the same method as in Example 3 with the formulations shown in Table 1, and the flammability and fluidity were further measured. The results are shown in Table 1.

Comparative Examples 1 to 3 To 100 parts by weight of HIPS, commercially available TBA (FG120G manufactured by Tosoh Corporation) was blended in the amounts shown in Table 2, and test pieces were prepared in the same manner as in Example 3, Further, a flammability test and fluidity (MFR) were measured. Table 2 shows the results.

[0063]

[Table 2]

Example 6 Brominated p-cumylphenol 585 having an average bromination number of 2.61 obtained in the same manner as in Example 1 was placed in a 1-liter four-neck round bottom separable flask equipped with a stirrer. 0.7 g
(1.372 mol) and tetrabromobisphenol-A
Diglycidyl ether (Toto Kasei YDB-400, epoxy equivalent: 398.3 g / eq.) 796.6 g
(0.70 mol) was charged and heated to 100 ° C. on an oil bath to melt.

Next, after charging 1.05 g (2.80 mmol) of tetraphenylphosphonium chloride, the mixture was heated to 160 ° C. and reacted for 4 hours, then poured into a metallic vat and cooled and solidified. , Target brominated p
-1140.6 g of cumylphenol derivative was obtained.

The results of elemental analysis, melting point, epoxy equivalent, nuclear magnetic resonance spectrum, infrared absorption spectrum and thermobalance measurement of the obtained target substance are shown below.

(1) Elemental analysis results C H Br Cl measured value (% by weight): 40.8 3.3 49.5 0.5 (2) Melting point: 88-96 ° C. (3) Epoxy equivalent: 30430 g / eq ． (4) Nuclear magnetic resonance spectrum (CDCl ₃ , H1, pp
m): δ1.62 (s, 20.7H), 3.58-3.
82 (m, 1.9H), 4.13-4.43 (m, 8.
7H), 6.97-7.43 (m, 17.7H) (5) Infrared absorption spectrum (KBr, cm ^-1 ): 355
9,2969,1586,1537,1468,139
0,1270,1093,1066,1008,93
3,873,825,740,659,573 (6) Thermobalance (° C): 5% weight loss (339), 10%
Weight loss (353), 50% weight loss (384).

Example 7 Brominated p-cumylphenol 271 having an average bromination number of 2.61 obtained in the same manner as in Example 1 was placed in a 1-liter four-neck round bottom separable flask equipped with a stirrer. .9 g
(0.63 mol) and tetrabromobisphenol-A diglycidyl ether (Toto Kasei YDB-406, epoxy equivalent: 651.4 g / eq.) 1302.8 g
(0.65 mol) was charged and heated to 100 ° C. on an oil bath to melt.

Next, after charging 0.98 g (2.61 mmol) of tetraphenylphosphonium chloride, the mixture was heated to 160 ° C., reacted for 3 hours, poured out into a metallic vat, cooled and solidified. , Target brominated p
-1114.4 g of cumylphenol derivative were obtained.

The results of elemental analysis, melting point, epoxy equivalent, nuclear magnetic resonance spectrum, infrared absorption spectrum and thermobalance measurement of the obtained target substance are shown below.

(1) Elemental analysis result C H Br Cl measured value (% by weight): 38.9 3.1 50.3 0.2 (2) Melting point: 98-116 ° C. (3) Epoxy equivalent: 1086 g / eq ． (4) Nuclear magnetic resonance spectrum (CDCl ₃ , H1, pp
m): δ1.61 (s, 18.9H), 2.71-2.
78 (m, 1.98), 2.99-3.07 (m, 1.
1H), 3.43-3.53 (m, 1.5H), 4.0
1-4.41 (m, 9.3H), 7.02-7.47.
(M, 14.7H) (5) Infrared absorption spectrum (KBr, cm ^-1 ): 355
4,2944,2368,1584,1536,141
1,1225,1094,1065,1023,97
8,842,714,642,573 (6) Thermobalance (° C): 5% weight loss (309), 10%
Weight loss (342), 50% weight loss (365).

Example 8 30 parts of the brominated p-cumylphenol derivative obtained in Example 6 was added to 100 parts by weight of an acrylonitrile / butadiene / styrene copolymer (hereinafter abbreviated as ABS; Toray # 10). By weight, 10 parts by weight of antimony trioxide were roll-kneaded at 210 ° C. and press-molded at 210 ° C. to prepare a sample piece. The combustion performance and fluidity (MFR; 220 ° C., 10 kg / cm ² ) of the obtained sample piece were measured. The results are shown in Table 3.

[0073]

[Table 3]

Example 9 To 100 parts by weight of ABS, 28 parts by weight of the brominated p-cumylphenol derivative obtained in Example 7, 9.3 parts by weight of antimony trioxide were added in the same manner as in Example 8. Combustion performance and fluidity (MFR; 220 ° C, 10 kg / cm
² ) was measured. The results are shown in Table 3.

Comparative Example 4 To 100 parts by weight of ABS, 30 parts by weight of a commercially available TBA-epoxy oligomer (TB-60 manufactured by Tohto Kasei: a reaction product of TBA-diglycidyl ether and tribromophenol in a 1/2 molar ratio) was used. Parts, and 10 parts by weight of antimony trioxide, were mixed in the same manner as in Example 8 to give combustion performance and fluidity (M
FR; 220 ° C., 10 kg / cm ² ) was measured. The results are shown in Table 3.

Comparative Example 5 To 100 parts by weight of ABS, 28 parts by weight of a commercially available TBA-epoxy oligomer (YDB-408 manufactured by Tohto Kasei: TBA-epoxy resin having a glycidyl group at a molecular end) and 9.monium trioxide were added. 3 parts by weight, compounded in the same manner as in Example 8, combustion performance and fluidity (MFR; 220 ° C, 1
0 kg / cm ² ) was measured. The results are shown in Table 3.

Example 10, Example 11, Comparative Example 6, Comparative Example 7 Specimen Eye Super UV Tester (33 mW / cm ² ) obtained in Example 8, Example 9, Comparative Example 4 and Comparative Example 5
Used, light resistance aging at 65 ° C. (formula △ E value _{= {(L-L 0)} 2 + (a-a 0) 2 + (b-
b ₀ ) ² } ^1/2 L ₀ , a ₀ , b ₀ : Measured value of sample piece before light resistance test L, a, b: Measured value of test piece after light resistance test ΔE by color difference meter Value) was measured. The results are shown in Table 4.

[0078]

[Table 4]

The brominated p-cumylphenol derivatives of Examples 8 and 9 were superior in light resistance to the commercial agents.

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Claims (13)

[Claims] 1. A brominated p-type compound represented by the following general formula (1):
Cumylphenol. Embedded image (In the formula, a represents an integer of 1 to 3, and b represents an integer of 1 to 2.) 2. The average bromination per molecule is from 2.5 to 2.5.
Brominated p- in the range of 4.0 and according to claim 1.
Cumylphenol was used in an amount of 0.001 to 30% by weight of dibromo compound, 30 to 99% by weight of tribromo compound, and 1 of tetrabromo compound.
The content of brominated p-cumylphenol is in the range of -80% by weight and 0.01-10% by weight of pentabromo compound. 3. A dibromo compound in an amount of 0.001 to 30% by weight,
30 to 95% by weight of tribromo compound and 1 of tetrabromo compound
Brominated p-cumylphenol according to claim 2, wherein the brominated p-cumylphenol is contained in an amount of 0.01 to 65% by weight and a pentabromo compound in an amount of 0.01 to 10% by weight. 4. The method for producing brominated p-cumylphenol according to claim 1, wherein p-cumylphenol is brominated with a brominating reagent in the presence of a catalyst. 5. The method for producing brominated p-cumylphenol according to claim 4, wherein the bromination reagent is bromine chloride. 6. The solution containing brominated p-cumylphenol obtained by the method according to claim 4 or 5, the solvent contained therein is distilled off, and then the impurities by-produced in the bromination reaction are removed. The method for recovering brominated p-cumylphenol according to any one of claims 1 to 3, wherein when a certain low-boiling substance is distilled off, it is distilled off by a steam distillation method. 7. A flame-retardant resin composition obtained by blending the brominated p-cumylphenol according to any one of claims 1 to 3 with a resin. 8. A blend of 5 to 50 parts by weight of the brominated p-cumylphenol according to claim 1 with respect to 100 parts by weight of the resin.
3. The flame-retardant resin composition according to item 1. 9. The following general formula (2): (In the formula, a is an integer of 1 to 3, b is an integer of 1 to 2, and n is 1
Represents the above integer. ) Or the following general formula (3): (In the formula, a is an integer of 1 to 3, b is an integer of 1 to 2, and n is 1
Represents the above integer. B) a brominated p-cumylphenol derivative represented by 10. The compound represented by the general formula (2) according to claim 9 is contained in an amount of 0 to 100 mol%, and the compound represented by the general formula (3) according to claim 9 is contained in an amount of 100 to 0 mol%. A brominated p-cumylphenol derivative characterized by containing in a range. 11. The brominated p-cumylphenol according to any one of claims 1 to 3 and the following general formula (4): (In the formula, m represents an integer of 0 or more.) An epoxy compound represented by the formula is reacted in the presence of a catalyst to produce a brominated p-cumylphenol derivative according to claim 9. Method. 12. A flame-retardant resin composition obtained by blending the brominated p-cumylphenol derivative according to claim 9 or 10 with a resin. 13. The method according to claim 9, with respect to 100 parts by weight of the resin.
Alternatively, 5 to 50 parts by weight of the brominated p-cumylphenol derivative according to claim 10 is blended, and the flame-retardant resin composition according to claim 12.