KR20100004848A - Flame retardant and impact modifier, method for preparing thereof, and thermoplastic resin composition containing the same - Google Patents

Abstract

PURPOSE: A thermoplastic resin composition containing frame retardant and impact modifier is provided to improve flame retardance and impact strength of the thermoplastic resin. CONSTITUTION: A flame retardant and an impact modifier are denoted by chemical formula 1. A method for producing the flame retardant and an impact modifier comprises: a step of reacting 2,4-ditertierybutylphenol with phosphorus oxychloride to prepare 2,4-ditertiarybutylphenyl dichlorophosphate; and a step of reacting phenol to the 2,4-ditertiarybutylphenyl dichlorophosphate. A thermoplastic resin composition contains 100 weight parts of thermoplastic resin and 0.1-30 weight parts of flame retardant and an impact modifier. The thermoplastic resin comprises 70-99 weight% of rubber-modified polystyrene system and 1-30 weight% of polyphenyleneether resin.

Description

Flame retardant and impact modifier, method for preparing the same and thermoplastic resin composition comprising same {Flame retardant and Impact Modifier, Method for Preparing Thereof, and Thermoplastic Resin Composition Containing the Same}

1 is an H-NMR spectrum of 2,4-dibutylbutylphenyl diphenylphosphate.

Field of invention

The present invention relates to a flame retardant and impact modifier, a method for producing the same, and a thermoplastic resin composition comprising the same. More specifically, the present invention relates to a thermoplastic resin composition which synthesizes phosphate having a specific substituent and applies it as a flame retardant and impact modifier, thereby improving flame retardancy and impact strength, as well as having excellent heat resistance and flow property balance.

Background of the Invention

Thermoplastic resins are applied to almost all electronic products because of their excellent processability and mechanical properties. However, the thermoplastic resin itself is easily burned and has no fire resistance. Therefore, the thermoplastic resin may be easily burned by the ignition source, and may serve to further spread the fire. In light of these reasons, countries that are legally regulated to use only polymer resins satisfying the flame retardant standards to ensure the safety of fire of electronic products are increasing.

Conventionally, a method of imparting flame retardant properties by applying a halogen-based compound and an antimony-based compound for flame retardation of a thermoplastic resin has been frequently used. Halogen-based compounds mainly used herein include polybromodiphenyl ether, tetrabromobisphenol A, brominated substituted epoxy compounds and chlorinated polyethylene. Antimony trioxide and antimony pentoxide are mainly used as an antimony compound.

Flame retardant method using halogen compound and antimony compound is excellent flame retardant effect and cost-effective flame retardant, housing material of electric or office equipment, ABS resin, PS, PBT, PET, epoxy It is used as main flame retardant, such as resin. However, it has been reported through experiments that the hydrogen halide gas generated during processing may have a fatal effect on the human body. In particular, polybromodiphenyl ether, which is used as a typical halogen flame retardant, is very interested in flame retardant methods that do not use such halogen-based compounds because very toxic substances such as dioxin bromide or furan bromide are generated during combustion. .

In particular, the rubber-modified styrene resin has a disadvantage in that it is difficult to expect a flame retardant effect in the solid phase because there is little char remaining during combustion (Journal of Applied Polymer Science, 1998, vol. 68, p. 1067). Therefore, by adding an additional char forming agent so that the char can be produced smoothly to obtain the desired flame retardancy.

As a technique for imparting flame retardancy without using a halogen flame retardant, the most common at present is to use a phosphate ester flame retardant. However, in order to exhibit the effect of flame retardancy by the addition of phosphate ester, there is a problem in that a predetermined amount or more of a flame retardant or a flame retardant aid is added.

US Patent No. 3,639,506 discloses a flame retardant resin composition which achieves flame retardancy by using triphenyl phosphate as a flame retardant in polyphenylene ether resin and styrene resin. However, this patent has a disadvantage in that juicing occurs during resin processing due to the low pyrolysis temperature of triphenylphosphate.

In order to solve the above problems, the present inventors have developed a phosphate having a specific substituent and applying it as a flame retardant and impact modifier, thereby having not only excellent flame retardancy and impact strength, but also thermoplastic having excellent physical property balance of heat resistance and fluidity. It is early to develop a resin composition.

An object of the present invention is to provide a flame retardant and impact modifier that can improve the excellent flame retardancy and impact strength in a small amount.

Another object of the present invention is to provide an environmentally friendly flame retardant and impact modifier without emitting a halogenated gas that causes environmental pollution during processing or combustion of the resin.

Still another object of the present invention is to provide a flame retardant and impact modifier that does not generate juice during resin processing.

Still another object of the present invention is to provide a flame retardant and impact modifier that can exhibit excellent balance of physical properties such as flame retardancy, impact strength, heat resistance, fluidity, and the like when applied to a thermoplastic resin.

Still another object of the present invention is to provide a method for preparing a new phosphate type compound in which a specific substituent is introduced, which can improve flame retardancy and impact strength.

Another object of the present invention is to provide a method capable of stably and efficiently preparing the phosphate compound having the specific substituent.

Still another object of the present invention is to provide a thermoplastic resin composition having excellent physical property balance by using the phosphate compound having a specific substituent as a flame retardant and impact modifier.

The above and other objects of the present invention can be achieved by the present invention described in detail.

Summary of the Invention

One aspect of the present invention provides phosphate compounds having specific substituents. The phosphate compounds can be used as flame retardant and impact modifiers. In embodiments, the flame retardant and impact modifier has the structure of Formula 1:

[Formula 1]

In an embodiment, the improving agent may be prepared by dehydrochlorination of phosphorus oxychloride and 2,4-dibutylbutylphenol under a metal catalyst.

In another embodiment, the improver may be prepared by reacting phenol with 2,4-dibutylbutylphenyl dichlorophosphate.

Another aspect of the present invention provides a new method for producing the flame retardant and impact modifier. In an embodiment the method comprises reacting phosphorus oxychloride with 2,4-dibutylbutylphenol to produce 2,4-dibutylbutylphenyl dichlorophosphate; And reacting phenol to the 2,4-dibutylbutylphenyl dichlorophosphate.

In a specific example, 3-6 equivalents of phosphorus oxychloride may be reacted with 1 equivalent of the 2,4-dibutylbutylphenol. In another embodiment, 2 to 4 equivalents of phenol may be reacted with 1 equivalent of 2,4-dibutyl butylphenyl dichlorophosphate.

Another aspect of the invention provides a thermoplastic resin composition comprising the flame retardant and impact modifier. In an embodiment the resin composition is 100 parts by weight of a thermoplastic resin; And 0.1 to 30 parts by weight of the flame retardant and impact modifier.

In one embodiment, the thermoplastic resin is polystyrene, styrene-acrylonitrile copolymer resin (SAN), rubber modified polystyrene resin (HIPS), rubber modified aromatic vinyl copolymer resin, ASA resin, MABS resin, polycarbonate resin, Polyphenylene ether resin, polyphenylene sulfide resin, polyester resin, polyolefin resin, poly (meth) acrylic resin, polyamide resin, polyvinyl chloride resin and the like can be used. These can be used individually or in mixture of 2 or more types.

In embodiments, the thermoplastic resin may be composed of 70 to 99% by weight of rubber-modified polystyrene resin and 1 to 30% by weight of polyphenylene ether resin. The resin composition may have a UL94 flame retardancy (1/8 ") of V-1 or V-0, and an impact strength (1/8" notch) of 10-50 kgfcm / cm as measured by ASTM D 256. have.

In another embodiment, the thermoplastic resin may be a polycarbonate resin. UL94 flame retardancy (1/8 ") of the said resin composition is V-0, and impact strength (1/8" notch) measured by ASTMD 256 may be 58-80 kgf * cm / cm.

In another embodiment, the thermoplastic resin may include 55 to 90 wt% of a polycarbonate resin and 10 to 45 wt% of a rubber-modified aromatic vinyl copolymer resin. UL94 flame retardancy (1/8 ") of the said resin composition is V-1 or V-0, and impact strength (1/8" notch) measured by ASTM D 256 can be 55-70 kgf * cm / cm. have.

In an embodiment, the resin composition may include additives such as heat stabilizers, lubricants, mold release agents, plasticizers, antistatic agents, flame retardant aids, anti drip agents, antioxidants, compatibilizers, light stabilizers, pigments, dyes and inorganic fillers. The additives may be used alone or in combination of two or more thereof. Hereinafter, the content of the present invention will be described in detail.

Detailed Description of the Invention

2,4-dibutylbutylphenyl diphenyl phosphate and preparation method

The phosphate compound of the present invention is characterized in that in one phenyl group of triphenol phosphate, a t-butyl group is present at a specific position as shown in the following general formula (1).

[Formula 1]

Conventional triphenylphosphate flame retardants are well known. However, when the triphenyl phosphate is applied as a flame retardant, the flame retardancy cannot be sufficiently expressed, there is a disadvantage that the impact strength is lowered when a large amount is used, and there is a problem such that processing is not easy due to the juice phenomenon. In the present invention, by introducing a t-butyl group at a specific position of one phenyl group of triphenol phosphate, not only the flame retardancy is remarkably improved, but also the impact strength can be improved and excellent physical property balance can be obtained.

If other alkyl groups such as methyl, ethyl, propyl, and n-butyl groups other than t-butyl groups are introduced, sufficient flame retardancy cannot be achieved, and there is a disadvantage in that the flame retardant is volatilized during processing.

In addition, when the t-butyl group is introduced in the 3,4-position or 2,6-position or 2,4,6-position, the synthesis is not easy, and the manufacturing process may be complicated, thereby increasing the manufacturing cost.

In an embodiment, the improving agent may be prepared by dehydrochlorination of phosphorus oxychloride and 2,4-dibutylbutylphenol under a metal catalyst. As the metal catalyst, metal chloride compounds such as magnesium chloride, aluminum chloride and calcium chloride may be used.

In another embodiment the improver can be prepared by reacting phenol with 2,4-dibutylbutylphenyl dichlorophosphate.

In another embodiment, 2,4-dibutylbutylphenyl dichlorophosphate is prepared by reacting phosphorus oxychloride with 2,4-dibutylbutylphenol; And reacting phenol to the 2,4-dibutylbutylphenyl dichlorophosphate.

In an embodiment, 3 to 6 equivalents of phosphorus oxychloride, preferably 4 to 5 equivalents, may be used based on 1 equivalent of 2,4-dibutylbutylphenol. When applied in the equivalent ratio can increase the completeness of the reaction, it can minimize the by-products.

When the phosphorus oxychloride and 2,4-dibutylbutylphenol are reacted, the reaction temperature is 80 to 160 ° C, preferably 100 to 150 ° C. In addition, the reaction is carried out under a metal catalyst, it is preferable to react under a nitrogen atmosphere. As the metal catalyst, metal chloride compounds such as magnesium chloride, aluminum chloride and calcium chloride may be used. The metal catalyst is used in the amount of 0.01 to 10 equivalents, preferably 0.01 to 5 equivalents, based on 1 equivalent of 2,4-dibutylbutylphenol. When applied in the equivalent ratio, the content of impurities can be minimized and economically preferable. The reaction time is 4 to 15 hours, preferably 5 to 10 hours.

When the phosphorus oxychloride reacts with 2,4-dibutylbutylphenol, 2,4-dibutylbutylphenyl dichlorophosphate in the liquid phase is obtained as an intermediate. Thereafter, phenol is added to the 2,4-dibutylbutylphenyl dichlorophosphate and reacted. At this time, it is preferable to react 2-4 equivalents of phenol with respect to 1 equivalent of 2, 4- dibutyl butylphenyl dichlorophosphate. When applied in the equivalent ratio can increase the completeness of the reaction, it can minimize the by-products. In this case, the reaction solvent may be added together with the phenol. As a reaction solvent that may be used, benzene, toluene, xylene, 1,4-dioxane, methylene chloride, ethylene chloride, and the like may be used, but are not necessarily limited thereto. These solvents may be used alone or in combination of two or more thereof.

When phenol is added to the 2,4-dibutylbutylphenyl dichlorophosphate and stirred at 100 to 130 ° C. for about 4 to 10 hours, a liquid phase 2,4-dibutylbutylphenyl diphenylphosphate can be obtained. The prepared 2,4-dibutylbutylphenyl diphenylphosphate may be further subjected to filtration and drying steps. In an embodiment, the dried product is washed with filtration and then dried in a vacuum oven to obtain a phosphate compound represented by Chemical Formula 1 in a yield of 85 to 99%.

Thermoplastic resin composition

It provides a thermoplastic resin composition comprising the flame retardant and impact improving agent of the present invention.

In an embodiment the resin composition is 100 parts by weight of a thermoplastic resin; And 0.1 to 30 parts by weight of the flame retardant and impact modifier.

The thermoplastic resin may be polystyrene, styrene-acrylonitrile copolymer resin (SAN), rubber modified polystyrene resin (HIPS), rubber modified aromatic vinyl copolymer resin, ASA resin, MABS resin, polycarbonate resin, polyphenylene ether Resins, polyphenylene sulfide resins, polyester resins, polyolefin resins, poly (meth) acrylic resins, polyamide resins, polyvinyl chloride resins and the like can be used. These can be used individually or in mixture of 2 or more types.

In one embodiment, the thermoplastic resin may be composed of 70 to 99% by weight of rubber-modified polystyrene resin and 1 to 30% by weight of polyphenylene ether resin.

The rubber-modified polystyrene resin is prepared by polymerizing a rubbery polymer and an aromatic vinyl monomer.

The rubbery polymers include butadiene-type rubbers, copolymers of butadiene and styrene, diene rubbers such as poly (acrylonitrile-butadiene), saturated rubbers hydrogenated with diene rubbers, isoprene rubber, acrylic rubber and ethylene-propylene- Diene monomer terpolymer (EPDM) and the like can be used. Preferably, polybutadiene, a copolymer of butadiene and styrene, isoprene rubber, alkyl acrylate rubbers and the like are used. The content of the rubbery polymer may be 3 to 30% by weight, preferably 5 to 15% by weight of the total weight of the rubber-modified polystyrene resin. The particle size of the rubber is preferably 0.1 to 4.0 ㎛. In the specific example, it is also possible to use a rubber dispersed in a bimodal or trimodal form.

As the aromatic vinyl monomer, styrene, α-methylstyrene, β-methylstyrene, p-methylstyrene, para t-butylstyrene, ethyl styrene, or the like may be used. The aromatic vinyl monomer may add 70 to 97% by weight, preferably 85 to 95% by weight of the total weight of the rubber-modified polystyrene resin.

The rubber-modified polystyrene resin of the present invention may be polymerized by adding monomers such as acrylonitrile, acrylic acid, methacrylic acid, maleic anhydride, N-substituted maleimide and the like to impart properties such as chemical resistance, processability, and heat resistance during manufacture. Can be. The amount to be added may be added to 40% by weight or less based on the entire rubber-modified polystyrene resin.

The rubber-modified polystyrene resin may be polymerized by thermal polymerization without the presence of an initiator, or may be polymerized in the presence of an initiator. Polymerization initiators that can be used include one or more selected from peroxide initiators such as benzoyl peroxide, t-butyl hydroperoxide, acetyl peroxide, cumenehydro peroxide, and azo initiators such as azobis isobutyronitrile. May be, but is not necessarily limited thereto.

The rubber-modified polystyrene-based resin may be prepared using bulk polymerization, suspension polymerization, emulsion polymerization or a mixture thereof, and among these polymerization methods, the bulk polymerization method may be preferably used.

The polyphenylene ether resin may be used to improve flame retardancy and heat resistance.

 Examples of the polyphenylene ether resin include poly (2,6-dimethyl-1,4-phenylene) ether, poly (2,6-diethyl-1,4-phenylene) ether, poly (2,6-di Propyl-1,4-phenylene) ether, poly (2-methyl-6-ethyl-1,4-phenylene) ether, poly (2-methyl-6-propyl-1,4-phenylene) ether, poly (2-ethyl-6-propyl-1,4-phenylene) ether, poly (2,6-diphenyl-1,4-phenylene) ether, poly (2,6-dimethyl-1,4-phenylene ) Copolymer of poly (2,3,6-trimethyl-1,4-phenylene) ether and poly (2,6-dimethyl-1,4-phenylene) ether and poly (2,3,5) Copolymers of -triethyl-1,4-phenylene) ether and the like, and mixtures thereof can also be applied. Preferably a copolymer of poly (2,6-dimethyl-1,4-phenylene) ether and poly (2,3,6-trimethyl-1,4-phenylene) ether and poly (2,6-dimethyl- 1,4-phenylene) ether is used, of which poly (2,6-dimethyl-1,4-phenylene) ether is most preferred. Although the polymerization degree of the said polyphenylene ether is not specifically limited, It is preferable that intrinsic viscosity measured in 25 degreeC chloroform solvent is 0.2-0.8 in consideration of the thermal stability and workability of a resin composition.

In a specific example, the polyphenylene ether resin can be used in the range of 1 to 30% by weight. When used in the above range, excellent flame retardancy, thermal stability and workability can be obtained. Preferably it is 15-30 weight%.

When the base resin is used as a blend of 70 to 99% by weight of rubber-modified polystyrene resin and 1 to 30% by weight of polyphenylene ether resin, the flame retardant and impact improving agent of the present invention is 10 to 30 parts by weight, preferably 15 to 25 parts by weight. Can be used as a wealth. These resin compositions have a UL94 flame retardancy (1/8 ") of V-1 or V-0 and an impact strength (1/8" notch) of 10-50 kgfcm / cm as measured by ASTM D 256. Can be.

In another embodiment, the thermoplastic resin may be a polycarbonate resin. The polycarbonate resin may have a weight average molecular weight of 10,000 to 500,000 g / mol, preferably, 15,000 to 100,000 g / mol. The balance between mechanical properties and moldability is excellent within the weight average molecular weight range of 10,000 to 500,000 g / mol.

As the polycarbonate resin, not only a linear polycarbonate resin, but also a branched polycarbonate resin or a polyester carbonate copolymer resin can be used without limitation.

When the base resin is used as the polycarbonate resin, the flame retardant and impact modifier of the present invention may be used in 1 to 15 parts by weight, preferably 3 to 10 parts by weight. These resin compositions may have a UL94 flame retardancy (1/8 ") of V-0 and an impact strength (1/8" notch) as measured by ASTM D 256 of 58-80 kgf cm / cm.

In another embodiment, the thermoplastic resin may include 55 to 90 wt% of a polycarbonate resin and 10 to 45 wt% of a rubber-modified aromatic vinyl copolymer resin.

In one embodiment, the rubber-modified aromatic vinyl copolymer resin may be composed of 20 to 50% by weight of rubbery polymer units, 40 to 60% by weight of aromatic vinyl units and 10 to 30% by weight of vinyl cyanide units.

Examples of the rubbery polymer include diene rubbers such as polybutadiene, poly (styrene-butadiene) and poly (acrylonitrile-butadiene), and acrylic rubbers such as saturated rubbers, isoprene rubbers and polybutylacrylic acid hydrogenated with the diene rubbers. Rubber and ethylene-propylene-diene monomer terpolymer (EPDM); Among these, especially diene rubber is preferable and butadiene rubber is more preferable. The average size of the rubber particles is preferably in the range of about 0.1 to about 4 ㎛ in consideration of impact strength and appearance.

Examples of the aromatic vinyl unit include styrene, α-methylstyrene, β-methylstyrene, p-methylstyrene, para t-butylstyrene, ethyl styrene, vinyl xylene, monochlorostyrene, dichlorostyrene, dibromostyrene, vinyl naphthalene, and the like. May be used, but it is not necessarily limited thereto. Of these, styrene is most preferred.

The vinyl cyanide unit includes acrylonitrile, ethacrylonitrile, methacrylonitrile, and the like, of which acrylonitrile is most preferred.

In addition, monomers such as acrylic acid, methacrylic acid, maleic anhydride, and N-substituted maleimide may be polymerized together in the rubber-modified aromatic vinyl copolymer resin, and workability and heat resistance may be further improved.

When using 55 to 90% by weight of polycarbonate resin and 10 to 45% by weight of rubber-modified aromatic vinyl copolymer resin as the base resin, the flame retardant and impact improving agent of the present invention is 15 to 30 parts by weight, preferably 20 to 25 parts by weight. Can be used as a wealth. These resin compositions have a UL94 flame retardancy (1/8 ") of V-1 or V-0, and an impact strength (1/8" notch) as measured by ASTM D 256 of 55-70 kgfcm / cm. have.

As the polyolefin resin, polyethylene resin, polypropylene resin, or the like may be used. In addition, polyethylene terephthalate, polybutylene terephthalate may be used as the polyester.

The resin composition of the present invention may include additives such as heat stabilizers, lubricants, mold release agents, plasticizers, antistatic agents, flame retardant aids, anti-drip agents, antioxidants, compatibilizers, light stabilizers, pigments, dyes and inorganic fillers. The additives may be used alone or in combination of two or more thereof. Examples of the added inorganic additives include asbestos, glass fibers, talc, ceramics, sulfates, and the like, which may be used in an amount of 30 parts by weight or less based on the total resin composition.

After the resin composition of the present invention is mixed with the above components and other additives simultaneously, it can be melt-extruded in an extruder and prepared in pellet form. The prepared pellets may be manufactured into various molded articles through various molding methods such as injection molding, extrusion molding, vacuum molding, and casting molding.

Another aspect of the present invention provides a molded article molded of the resin composition. The molded article is excellent in impact resistance, fluidity, flame retardancy, thermal stability, etc., and does not generate a juice phenomenon, so it is widely applicable to parts, exterior materials, automobile parts, sundries, structural materials of electrical and electronic products.

The invention can be better understood by the following examples, which are intended for the purpose of illustration of the invention and are not intended to limit the scope of protection defined by the appended claims.

Example

Preparation Example: Preparation of 2,4-dibutylbutylphenyl diphenyl phosphate

Phosphorus oxychloride (767g, 5.0 mol), 2,4-dibutylbutylphenol (206g, 1mol) and magnesium chloride (1g, 0.01mol) were added to a vessel and stirred at 130 ° C. for 6 hours under a nitrogen atmosphere. The temperature of the vessel was reduced to 90 ° C. and the pressure was reduced to recover residual phosphorus oxychloride, and phenol (188 g, 2 mol) and toluene (1 L) were added, followed by stirring at 130 ° C. for 5 hours under a nitrogen atmosphere. After completion, the temperature was lowered to room temperature, water (1L) was added, the mixture was stirred, the organic layer was taken, and distilled under reduced pressure to obtain 2,4-dibutylbutylphenyl diphenylphosphate having a purity of 98% or more and a yield of 95%.

Example 1

To 75 parts by weight of rubber-reinforced styrene resin (HIPS, HG-1760S, manufactured by Cheil Industries, Ltd.) to 25 parts by weight of poly (2,6-dimethyl-phenylether) (PPE trade name: PX-100F) manufactured by Mitsubishi Engineering Plastics, Japan 2,4-dibutylbutylphenyl diphenylphosphate prepared in Preparation Example was added to the blend in the ratio of the following Table 1 and extruded in a conventional twin screw extruder at a temperature range of 200 ~ 280 ℃ to prepare a pellet. The prepared pellets were dried at 80 ° C. for 2 hours, and then injected into a molding machine at a molding temperature of 180 to 280 ° C. and a mold temperature of 40 to 80 ° C. to prepare a flame retardant specimen. The prepared specimens were measured for flame retardancy at a thickness of 1/8 ″ according to UL 94 VB flame retardant regulations, and the impact strength was in accordance with ASTM D 256 (1/8 ″ notch, kgf · cm / cm).

Examples 2 to 3

The base resin was used in the same manner as in Example 1 except that polycarbonate resin (Japan Teijin Panlite L-1225 Grade) was used and the content of 2,4-dibutylbutylphenyl diphenyl phosphate was changed.

Example 4

Basic resin is polycarbonate resin (Japan Teijin Panlite L-1225 Grade) and ABS (g-ABS / SAN 3/7, g-ABS is Cheil Industries CHT, SAN is Cheil Industries AP-70). The same procedure as in Example 1 was carried out except that the content of dietary butylphenyl diphenyl phosphate was changed.

Comparative Examples 1 to 4

Triphenyl phosphate (Daihachi Co., Ltd.) was used as a flame retardant, and the same procedure as in Example 1 was performed except that the composition was changed as shown in Table 1 below. All the measurement results are shown in Table 1.

From the results of Table 1, it can be seen that the use of 2,4-dibutylbutylphenyl diphenyl phosphate is superior in flame retardancy and impact strength at a thickness of 1/8 "than when applying the triphenyl phosphate.

Comparative Examples 5-8

Except for using 2,4,6-trimethylphenyldiphenyl phosphate as flame retardant was carried out in the same manner as in Examples 1 to 4. All the measurement results were shown in Table 2.

As shown in Table 2, when using 2,4-dibutylbutylphenyl diphenyl phosphate, flame retardancy and impact strength at a thickness of 1/8 ″ than when applying 2,4,6-trimethylphenyldiphenyl phosphate It can be seen that is excellent.

       The present invention can improve the excellent flame retardancy and impact strength even with a small amount, and does not emit halogenated gas causing environmental pollution during processing or combustion, it is environmentally friendly and does not generate juice, flame retardancy, impact when applied to a thermoplastic resin It has the effect of providing the flame retardant and impact improver capable of expressing excellent physical properties such as strength, heat resistance, flowability, a method for producing the same, and a thermoplastic resin composition using the same.

Simple modifications and variations of the present invention can be readily used by those skilled in the art, and all such variations or modifications can be considered to be included within the scope of the present invention.

Claims (13)

Flame retardant and impact modifier represented by the formula (1): [Formula 1]

     The flame retardant and impact modifier of claim 1, wherein the improving agent is prepared by dehydrochlorination of phosphorus oxychloride and 2,4-dibutylbutylphenol under a metal catalyst.      The flame retardant and impact modifier of claim 1, wherein the modifier is prepared by reacting phenol with 2,4-dibutylbutylphenyldichlorophosphate. Reacting phosphorus oxychloride with 2,4-dibutylbutylphenol to prepare 2,4-dibutylbutylphenyl dichlorophosphate; And Reacting phenol with the 2,4-dibutylbutylphenyl dichlorophosphate; Method for producing a flame retardant and impact improver represented by the following formula (1) comprising a step: [Formula 1]

The method according to claim 4, wherein 3 to 6 equivalents of phosphorus oxychloride is reacted with 1 equivalent of 2,4-dibutylbutylphenol. The method according to claim 4, wherein 2 to 4 equivalents of phenol are reacted with respect to 1 equivalent of 2,4-dibutylbutylphenyl dichlorophosphate. 100 parts by weight of thermoplastic resin; And 0.1 to 30 parts by weight of a flame retardant and impact modifier represented by Formula 1 below; Thermoplastic resin composition comprising: [Formula 1]

The method of claim 7, wherein the thermoplastic resin is polystyrene, styrene-acrylonitrile copolymer resin (SAN), rubber modified polystyrene resin (HIPS), rubber modified aromatic vinyl copolymer resin, ASA resin, MABS resin, polycarbonate At least one selected from the group consisting of resins, polyphenylene ether resins, polyphenylene sulfide resins, polyester resins, polyolefin resins, poly (meth) acrylic resins, polyamide resins, and polyvinyl chloride resins. Thermoplastic resin composition. The method of claim 8, wherein the thermoplastic resin is a thermoplastic resin composition, characterized in that consisting of 70 to 99% by weight of rubber-modified polystyrene resin and 1 to 30% by weight of polyphenylene ether resin. The resin composition of claim 9, wherein the UL94 flame retardancy (1/8 ") is V-1 or V-0, and the impact strength (1/8" notch) measured by ASTM D 256 is 10-50. It is kgf * cm / cm, The thermoplastic resin composition characterized by the above-mentioned. The method of claim 8, wherein the thermoplastic resin is a polycarbonate resin, the UL94 flame retardancy (1/8 ") of the resin composition is V-0, and the impact strength (1/8" notch) measured by ASTM D 256 is It is 58-80 kgf * cm / cm, The thermoplastic resin composition characterized by the above-mentioned. The method of claim 8, wherein the thermoplastic resin is 55 to 90% by weight of polycarbonate resin and 10 to 45% by weight of the rubber modified aromatic vinyl copolymer resin, UL94 flame retardancy (1/8 ") of the resin composition is V The thermoplastic resin composition of -1 or V-0, and impact strength (1/8 "notch) measured by ASTM D 256 is 55-70 kgf * cm / cm. 8. The method of claim 7, wherein the resin composition further comprises at least one thermal stabilizer, lubricant, mold release agent, plasticizer, antistatic agent, flame retardant aid, anti-drip agent, antioxidant, compatibilizer, light stabilizer, pigments, dyes and inorganic fillers. The thermoplastic resin composition characterized by the above-mentioned.

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