DE2750242A1 - THERMOPLASTIC COMPRESSION COMPOUNDS - Google Patents

Description

Thermoplastic molding compounds

The invention relates to thermoplastic molding compositions made from a polyphenylene ether resin, a styrene resin and a radial teleblock copolymer of a vinyl aromatic compound and a saturated rubber. The masses according to the invention provide molded articles with good mechanical properties, for example, improved impact resistance. Reinforced and flame retardant compounds are also provided.

The polyphenylene ether resins are a family of engineering thermoplastics known in polymer technology. These Polymers can be through various catalytic and non-catalytic Process can be prepared from corresponding phenols or their reactive derivatives. For example, certain

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te polyphenylene ethers in U.S. Patents 3,306,874 and 3,306,875 (Hay) and in U.S. Patents 3,257,357 and 3,257,358 (Stamatoff) described. According to U.S. Patents 3,306,874 and 3,306,875 (Hay) the polyphenylene ethers are produced by an oxidative coupling reaction in which an oxygen-containing gas is used by the reaction solution of a phenol and a metal / amine complex catalyst directs. Other descriptions of processes for making polyphenylene ether resins, including Graft copolymers and polyphenylene ethers with styrene-like compounds are found, for example, in US Pat. No. 3,356,761 (Fox); British Patent 1,291,609 (Sumitomo); U.S. Patent 3,337,499 (Bussink et al.); Blanchard et al. U.S. Patent 3,219,626; U.S. Patent 3,342,892 (Laakso et al.); Borman U.S. Patent 3,344,166; U.S. Patent 3,384,619 (Hori et al.); U.S. Patent 3,440,217 (Paurote et al.); Descriptions of metal-based catalysts without amines are for example from U.S. Patent 3,442,885 to Wieden et al .; copper amidines; U.S. Patent 3,573,257 (Nakashio et al .; metal alcoholates or phenates); U.S. Patent 3,455,880 (Kobayashi et al .; cobalt chelates) is known. According to the Stamatoff patents, the polyphenylene ethers are produced by the corresponding phenolation with a Starter, for example a salt of a peroxy acid, an acid peroxide or a hypohalite, in the presence of a complexing agent Implemented means. Descriptions of non-catalytic processes, for example oxidation with lead dioxide or silver oxide, can be found in U.S. Patent 3,382,212 (Price et al.). In US-PS 3,383,435 (Cizek) polyphenylene ethers / Described styrene resin compositions. The disclosure content of all of the above said patent specifications are incorporated into the present application by this reference.

The processability of polyphenylene ether resins by injection molding and extrusion devices is improved if the Polyphenylene ethers can be combined with styrene resins, for example with crystalline homopolystyrene or with a rubber-modified one high impact polystyrene. These polymers can be combined with one another in a wide range of ratios.

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bar, for example in a range from 1 to 99 parts of polyphenylene ether and 99 to 1 parts of styrene resin. Compounds with 10 to 60 parts of polyphenylene ether and 90 to 40 parts of styrene resin offer particularly desirable shaping properties.

Such combinations are disclosed in US Pat. No. 3,383-435 (Cizek) described. The thermoplastic compounds described by Cizek include rubber-modified, high-impact-resistant materials Styrene resins / as well as homopolystyrene. High-impact styrene resins are particularly useful for the production of polyphenylene ether masses, which have good impact resistance.

In DT-OS 2 713 509 it is described that compositions of a polyphenylene ether resin, a styrene resin and a radial teleblock copolymer a vinyl aromatic compound and a conjugated diene, e.g. a styrene / butadiene radial teleblock copolymer, Provide molded articles with good impact resistance.

It has now surprisingly been found that in the production of compositions of a polyphenylene ether resin, a styrene resin and a hydrogenated radial teleblock copolymer one vinyl aromatic compound and a saturated rubber, the masses formed molded articles with improved surface gloss deliver.

It was found that the hydrogenated radial teleblock copolymers according to the invention with compositions with a relatively high content of polyphenylene ether resin, for example 50 parts by weight or more, and low molecular weight crystalline polystyrene as well as masses with a relatively low content of polyphenylene ether resin, for example 35 parts by weight or less, and high-impact polystyrene are compatible and usable for them.

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As used herein, the term "hydrogenated radial teleblock copolymer" denotes branched polymer with sections or segments or blocks, the saturated rubber, blocks of a vinyl aromatic polymer and a coupling agent include. In particular, the interpolymer has a structure in which several chains of rubber, generally three or more, start from a coupling agent, each chain at its other end with a block of the vinyl aromatic polymer is provided. It is generally believed that the incompatibility of the block segments in the radial teleblock copolymer promotes the formation of a two-phase system in which the blocks of vinyl aromatic polymer separate to form separate ones or discrete areas or "domains" unite. These areas simulate crosslinking between the chains of the elastomer; in this way a branched elastomer network with blocks of a saturated rubber, blocks of a vinyl aromatic Polymers and formed with a coupling agent.

Radial teleblock copolymers are known in the art. For example, detailed descriptions of these materials are provided by Marrs et al. in AdhesivesAge, December 1971, pages 15-20, and by Haws et al. in Rubber World, January 1973, pages 27 to xo "~" _ö x ~ ^ _Λ ** ι. ^the present. Application included 5 <? I GegeDen, the disclosure of which is incorporated by this reference in /. The hydrogenation of radial teleblock copolymers is also known in the art.

According to the invention, thermoplastic molding compounds are provided which are an intimate mixture of:

(i) a polyphenylene ether resin;

(ii) a styrene resin; and

(iii) a hydrogenated radial teleblock copolymer of a vinyl aromatic compound, a saturated rubber and a coupling agent.

In the context of the invention described above, the styrene resin component (ii) can either be homopolystyrene

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or a rubber modified high impact polystyrene Act. The radial teleblock copolymer (iii) is preferably a branched copolymer of styrene and a hydrogenated one Rubber that contains a relatively small effective amount of a coupling agent selected from the epoxidized polybutadiene (e.g. Oxiron 2000 or Oxiron 2001) SiCl ^ or mixtures thereof Group contains.

The polyphenylene ether resin (i) is preferably a compound with recurring units of the formula:

each oxygen ether atom of each unit with the benzene nucleus the next adjacent unit, η is a positive integer and at least 50 and each Q residue is a monovalent Substituent from the hydrogen atoms, halogen atoms, Hydrocarbon radicals without tertiary alpha carbon atoms, Halocarbon groups and halocarbon oxy groups with at least 2 carbon atoms between the halogen atom and the phenyl nucleus and hydrocarbonoxy radicals formed group.

Examples of polyphenylene ethers corresponding to the above formula can be found in the Hay and Stamatoff patents cited above.

According to the invention includes; a particularly preferred group of Polyphenylenätliern compounds in the two ortho positions are alkyl-substituted to the oxygen ether atom, i.e.

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Compounds of the above formula in which Q is in each case an alkyl group, in particular having 1 to 4 carbon atoms. The most preferred Polyphenylenatherharz is poly (2,6-dimethyl-1,4-phenylene) ether, preferably having an intrinsic viscosity of about 0.5 dl / g (measured in chloroform at 30 ⁰ C).

Preferred styrene resins (ii) are compounds having at least 25 wt .- / 6 repeating units which differ from a vinyl aromatic Derive monomers from the following formula:

1 2

where R and R from the hydrogen atoms and lower Alkyl or alkenyl groups having 1 to 6 carbon atoms are formed Group are selected; P / and R from the chlorine, bromine and hydrogen atoms and lower alkyl groups with 1 to 6 Group formed by carbon atoms are selected; and R ^ and R from the group consisting of hydrogen atoms and lower alkyl and alkenyl groups are selected with 1 to 6 carbon atoms or where R ″ and R with the hydrocarbon groups can be linked to form a naphthyl group. These compounds are free from substituents with tertiary carbon atoms.

include specific examples of vinyl aromatic monomers / styrene, Chloratyrene, alpha-methylstyrene, vinylxylene, divinylbenzene and Vinyl naphthalene.

Vinyl aromatic monomers can be copolymerized with the materials are, for example, compounds of the general formula:

R ⁷ -C (H) _n C (R ⁸ ) - - - (CH ₂ ) _m - R ⁹

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where the dashed lines each represent a carbon-carbon

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represent a single or double bond, R 'and R together

represent a -CO-O-CO bond, R ⁷ from which by hydrogen atoms, vinyl, O ^ _ ^ p-alkyl, C ^ g-alkenyl, C. ^ p-alkylcarboxyl and C _x , ^, p-alkenylcarboxyl groups is selected; η = 1 or 2 depending on the position of the carbon-carbon double bond and m is an integer from 0 to about 10. Examples are maleic anhydride, citraconic anhydride, itaconic anhydride and aconitic anhydride.

For example, the styrene resins (ii) include homopolymers, such as polystyrene and monochloropolystyrene, modified polystyrenes, such as rubber modified high impact polystyrenes, and styrene-containing copolymers, such as styrene / acrylonitrile copolymers, Styrene / butadiene copolymers, styrene / acrylonitrile / alpha-alkylstyrene copolymers, Styrene / acrylonitrile / butadiene copolymers, Poly-alpha-methylstyrene, mixed polymers from ethyl vinylbenzene and divinylbenzene, styrene / maleic anhydride copolymers, Styrene / butadiene / styrene block copolymers and styrene / butadiene block copolymers and styrene / butadiene / styrene / Maleic anhydride block copolymers.

The styrene / maleic anhydride interpolymers are disclosed in the U.S. patents 3,971,939, 3,336,267 and 2,769,804, the disclosure of which is incorporated into the present application by this reference will.

Particularly preferred styrene resins are homopolystyrene and rubber-modified high-impact polystyrene resins that have been modified with natural or synthetic polymer materials that are elastomers at room temperature, for example at 20 to 25 ^° C., for example polystyrene resins that contain polybutadiene or rubber-like styrene / butadiene copolymers.

A rubber-modified high-impact polystyrene with a content of about 8 % polybutadiene rubber is preferred

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(FG 83'4 of the Poster-Grant Co.). A preferred low molecular weight homopolystyrene has a number average molecular weight of about 40,000 (KPTL-5 from Arco Polymers, Inc., Pittsburgh, Pa.). A preferred relatively high molecular weight homopolystyrene has a number average molecular weight of about 150,000 (DYL-8G from Arco).

Radial teleblock copolymers are commercially available or can be made according to prior art teachings in Teohnik will. For example, they can be prepared by using conjugated dienes such as butadiene and vinyl aromatic Compounds, e.g. styrene, are polymerized in the presence of an organometallic initiator, e.g. n-butyllithium and mixed polymers with an active metal atom, e.g. Lithium, at one end of each polymer chain. These Polymers with terminal metal atoms are then reacted with a coupling agent that has at least 3 active sites having those with the carbon-metal atom bonds of the polymer chains can react and replace the metal atoms of the chains. This leads to polymers with relatively long Branches that start from a core, that of the polyfunctional one Coupling agent is formed. One such method of manufacture is detailed in US Pat. No. 3,281 (Zelinski et al.), Whose disclosure content by this reference is included in the present application.

As coupling agents for the radial teleblock copolymers, for example, polyepoxides, polyisocyanates, polyimines, Choose polyaldehydes, polyketones, polyanhydrides, polyesters or polyhalides. These materials can be two or contain several types of functional groups, for example a combination of epoxy and aldehyde groups or isocyanate and halide groups. The coupling agents are detailed in U.S. Patent 3,281, cited above described.

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To the conjugated dienes for radial teleblock copolymers include, for example, 1,3-butadiene, isoprene, 2,3-dimethyl-1 , 3-butadiene, 1,3-pentadiene and 3-butyl-1,3-octadiene.

The vinyl aromatic polymers can be prepared from vinyl aromatic compounds of the formula II. This includes Styrene, 1-vinylnaphthalene, 2-vinylnaphthalene and their alkyl, Cycloalkyl, aryl, alkaryl and aralkyl derivatives. Examples include 3-methylstyrene, 4-n-propylstyrene, 4-cyclohexylstyrene, 4 ~ dodecylstyrene, 2-ethyl- '»- benzylstyrene, 4-p-tolylstyrene and 4- (4-phenyl-n-butyl) styrene.

The hydrogenation of radial teleblock copolymers for manufacture of hydrogenated radial teleblock copolymers (III) can be carried out by any known procedure. Comparisons for example, U.S. Patent 3,696,088 (De Vault), the disclosure of which is incorporated into the present application by this reference.

In preferred compositions, the hydrogenated radial teleblock copolymer is a radial teleblock copolymer composed of styrene and a saturated rubber with terminal blocks extending from Derive styrene, and a coupling agent formed from the epoxidized polybutadiene, SiCl ^ and their mixtures Group. Particularly preferred epoxidized polybutadiene coupling agents are commercially available (trade names Oxiron 2000 and Oxiron 2001).

The molecular weight of the hydrogenated radial teleblock copolymer and the proportions of its mixed monomers can be largely vary. In preferred embodiments, the molecular weight of the hydrogenated radial teleblock copolymer is about 75,000 to about 350,000; it contains 1 to 45 parts by weight vinyl aromatic compound and 99 to 55 parts by weight of unsaturated rubber based on the weight of the radial teleblock copolymer. The amount of coupling agent in the copolymer depends on the agent and the amount of

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deten organometallic initiator. In general, relatively small amounts of coupling agent are used, for example 0.1 to 1 part by weight per 100 parts by weight of resin.

Preferred hydrogenated radial teleblock copolymers contain about 70 parts by weight of hydrogenated butadiene units and about 30 Parts by weight of styrene units (Solprene 502 and 512 from Philips Petroleum Co., Stowe, Ohio). These materials also contain relatively small amounts of a coupling agent, e.g., less than 1 part by weight of coupling agent per 100 parts by weight of the copolymer.

Components (i), (ii) and (iii) are quite broad Quantity range can be combined. The compositions according to the invention preferably contain about 10 to about 65 parts by weight of polyphenylene ether resin (i), about 90 to about 35 parts by weight of styrene resin (ii) and about 1 to about 25 parts by weight of a hydrogenated radial teleblock copolymer (iii) based on the total weight of the composition .

The compositions according to the invention can also contain other ingredients, for example flame retardants, extenders, Processing aids, pigments and stabilizers accordingly, their usual uses. Reinforcing fillers can be used in amounts sufficient for reinforcement e.g. aluminum, iron or nickel, and non-metals such as carbon filament, silicates e.g. acicular Calcium silicate, asbestos, titanium dioxide, potassium titanate and titanate hair crystals, glass flakes and fibers. If the filler does not add anything to the strength and rigidity of the mass, it is just a filler and is not used as a reinforcing filler Understood. In particular, the reinforcing fillers increase the flexural strength, the flexural modulus, the tensile strength and the Heat deformation temperature.

In particular, the preferred reinforcing fillers are made from glass, preferably from fibrous glass filaments with inclusion of calcium oxide / aluminum borosilicate glass, which is relatively

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is soda free. It is known as the "E" glass.

In general, the best properties are obtained when the classified Glasverstärkungsfilamente about 1 to about 80 wt -.% Based on the total weight of glass and polymer, and preferably about 10 to about 50 #i in particular 10 to 40 wt .-% account.

According to the invention, flame-retardant compositions are provided which a flame-retardant additive made from halogenated organic compounds, halogenated organic compounds in a mixture with antimony compounds, elemental phosphorus or phosphorus compounds or compounds with phosphorus-nitrogen bonds and mixtures of two or more of these compounds.

In general, the amount of the flame retardant additive is about 0.5 to 50 parts by weight per 100 parts of the components (i), (ii) and (iii).

The compositions according to the invention can be prepared by first dry mixing the components to form a premix and then the premix sends through an extruder at elevated temperature, for example at 218-338 ⁰ C (425-640 ⁰ P) by conventional methods.

For example, Glasvorgespinst is (a bundle of filament strands) chopped into small pieces, for example, a length of 0.32 _D i _s 2,54- cm (1/8 to 1 ") and preferably less than 0,64- cm (1/4 - "), into an extrusion compounder with (i) the polyphenylene ether resin, (ii) the styrene resin, (iii) the hydrogenated radial teleblock copolymer, and (iv) the flame retardant additives / to make pellets for molding. The fibers are shortened and predispersed in this work routine and are less than 0.16 cm (1/16 ") in length. In another

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Working method, the glass filaments are cut into shorter lengths or ground, with the polyphenylene ether resin, the styrene resin, the radial teleblock copolymer and optionally a flame retardant additive mixed by dry blending and then either agitated (fluxed) and crushed with a mill or extruded and chopped.

The compounding should be carried out in such a way that it is ensured that the residence time in the device is short that the Temperature is carefully controlled so that the frictional heat is exploited and that an intimate mixture of the resins and the Additives is obtained.

The invention thus relates to thermoplastic compositions which can be molded into objects of high impact resistance and which is an intimate mixture of a polyphenylene ether resin, of a styrene resin and a radial teleblock mixing polymer from a vinyl aromatic compound, a saturated rubber and a coupling agent. This includes also reinforced and flame-retardant compositions made of the thermoplastic materials mentioned.

The invention is explained in more detail below by means of examples. Comparative example 1 (sample A)

A premix of 55 parts by weight of poly (2,6-dimethyl-1,4-phenylene) ether resin (PPO) and 45 parts by weight of a rubber-modified polystyrene with about 8 # polybutadiene rubber (Foster-Grant's Fostuflex 834 (FG 834)) by dry mixing these components with 4 parts of triphenyl phosphate, 1.5 parts of polyethylene, 1 part of tridecyl phosphite, 0.15 part of zinc sulfide and 0.15 part of zinc oxide. Thereafter, the premix was compounded on a 28 mm Doppeischneckenextruder at about 260 ⁰ C (500 ⁰ F). The extrudate was cooled and ground into pellets, and the pellets were used as test sticks

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molded on a Newbury injection molding machine. Example 1 (sample B)

Comparative Example 1 was repeated except that the 45 parts of the rubber-modified polystyrene with about 8% polybutadiene rubber (FG 834) by 30 parts of a "crystalline" polystyrene (Sinclair-Kopper Co.'s Dylene-8G (DYL-8G)) and a radial teleblock copolymer with hydrogenated rubber blocks (Phillips Petroleum's Solprene 5O2CX (SOL-502)).

Example 2

The masses in the comparative example and in the example 1 were tested and the following results were obtained:

Ground TYTE Izod GIMP HDlV ( ⁰ C) ( ⁰ F) GLOSS MV

Sample A 8900 83 3.0 210 Sample B 7900 20 6.0 225

118

126

245
259

53 65

2100 2150

T.Y. T.E. Izod

GIMP HDT GLOSS HV

Tensile Strength (psi = 0.07 kg / cnr) Tensile elongation

Notched Izod Strength (ft. Lbs./in. Notch = 0.3 m χ 0.45 kg / 2.54 cm notch)

Gardner Impact Strength (in. Lbs. = 2.54 cm 0.45 kg)

Heat distortion temperature

Surface gloss (45 "= 114 cm, dimensionless) Melt viscosity at 282 ⁰ G (540 ⁰ Jj ¹ ), 1500 sec" ¹ (Poise)

From the above, it can be seen that a thermoplastic composition according to the invention (sample B) exhibits improved impact resistance and an unexpected improvement in surface gloss over a typical known composition (sample A).

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Comparison example 2 (sample G)

A premix of 50 parts by weight of PPO and 50 parts by weight of a rubber-modified polystyrene with about 8 # polybutadiene rubber (FG 83 *) was prepared by mixing these components with 3 parts of triphenyl phosphate, 1.5 parts of polyethylene, 1 part Tridecyl phosphite, 0.15 part zinc sulfide, 0.15 part zinc oxide and 3 parts titanium dioxide. The premix was then compounded on a 28 mm twin-screw extruder at about 260 ⁰ C (500 ⁰ P). The extrudate was cooled and chopped into pellets, and the pellets were molded into test bars with a Newbury injection molding machine.

Comparative Example 3 (Sample D)

Comparative Example 2 was repeated with the exception that the 50 parts of the rubber-modified polystyrene with about 8 # polybutadiene rubber (PG 83 *) by 42 parts of a "crystalline ¹¹ polystyrene (DYL-8G) and 8 parts of a radial teleblock copolymer with styrene and butadiene (Phillips Petroleum's Solprene (SOL-411)) have been replaced.

Example 3 (sample E)

The procedure of Comparative Example 2 was repeated with the exception that the 50 parts of the rubber-modified polystyrene with about 8 % polybutadiene (PG 834) were replaced by 38 parts of a "crystalline" polystyrene (DYL-8G) and 12 parts of a radial teleblock copolymer with hydrogenated rubber blocks (SOL -502) have been replaced.

Example 4

The masses used in Comparative Examples 2 and 3 and in Example 2 were studied to determine the effects of aging; the following results were obtained:

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Izod T.E.

Tapre at 115 ⁰ C C. 5 D. E. C. D. E. 6th 4, O 4.0 4.3 94 89 25th 11 3, 2 3.3 2.5 30th 20th 16 28 2, O 2.1 2.4 16 7th 13th 50 1, 1.1 1.9 6th 6th 10 63 1.8 9 91 1.3 8th

The results clearly show that the toughness at Heat aging of sample E (composition according to the invention) is maintained over samples C and D (two known compositions).

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Claims (1)

Dr. rer. not. Horst Schuler PATENT ADVOCATE 6000 Frankfurt / Main 1, November 9th Kaiserstrasse 41 Hk Telephone (0611) 235555 Telex: 04-16759 mapat d Postal check account: 282420-602 Frankfurt / M. Bank account: 225/0389 Deutsche Bank AG, Frankfurt / M. 4490-3CH-2419 GENERAL ELECTRIC COMPANY 1, River Road
Schenectady, NY, USA PATENT CLAIMS 1. Thermoplastic molding compound, characterized in that it in an intimate mixture contains: (i) a polyphenylene ether resin, (ii) a styrene resin and (iii) a hydrogenated radial teleblock copolymer composed of a vinyl aromatic polymers, a saturated rubber and a coupling agent. Poly-2 · Preomasse according to claim 1, characterized in that it is a / phenylenätherharζ with repeating units of the following Structural formula: having, 809825/06 * 0 where the ether oxygen atom of each unit is connected to the benzene nucleus of the next neighboring unit, η is a positive integer and at least 50 and each Q radical is a monovalent substituent selected from the hydrogen atoms, halogen atoms, hydrocarbonoxy radicals, hydrocarbon radicals without tertiary alpha carbon atoms, is halogen hydrocarbon radicals or Halogenkohlenwasserstoffoxyreste having at least two carbon atoms between the halogen atom and the phenol nucleus formed group and wherein at least 25 wt -% of the recurring units of the styrene resin derived from a vinyl aromatic monomer of the following formula.: CR ¹ = · CHR ² 1 2
wherein R and R are selected from the groups formed by hydrogen atoms and lower alkyl groups or alkenyl groups having 1 to 6 carbon atoms, R ^ and .R are selected from the group formed by chlorine atoms, bromine atoms, hydrogen atoms and lower 0> _{Λ A} alkyl groups and R ^? and R are selected from the group formed by hydrogen atoms and lower alkyl groups and alkenyl groups having 1 to 6 carbon atoms, or C sr R ^p and R are linked to the hydrocarbon groups to form a naphthyl group, these compounds not having any substituents with a tertiary carbon atom. 3. molding compound according to claim 1 or 2, characterized by poly (2,6-dimethylphenylene-1,4) ether as a polyphenylene ether resin. 4. molding compound according to one of the preceding claims, characterized by using a low molecular weight homopolystyrene as the styrene resin. 809825/0640 5 · molding compound according to one of claims 1 to 3 »characterized by a rubber-modified, high-impact polystyrene than styrene resin. 6. molding compound according to one of the preceding claims, characterized in that the radial teleblock copolymers 1 to 4-5 parts by weight of the vinyl aromatic polymer and accordingly Contains 99 to 55 parts by weight of the saturated rubber. 7. molding compound according to one of the preceding claims, characterized by a polymer from which by polyepoxides, polyisocyanates, polyimines, polyaldehydes, polyketones, polyanhydrides, Polyesters and polyhalides formed group as coupling agents. 8. molding compound according to claim 1, characterized by a radial teleblock copolymer with polystyrene as vinyl aromatic compound, with polybutadiene as saturated rubber and with a coupling agent from the epoxidized polybutadiene, Silicon tetrachloride and their mixtures formed group. 9 · molding compound according to one of the preceding claims, characterized by 10 to 65 wt. # of the polyphenylene ether resin, 90 to 35 wt. # of the styrene resin, and 1 to 25 wt. # of the radial teleblock copolymer based on the total weight of the mass. 10. molding compound according to one of the preceding claims, characterized characterized in that it further comprises a reinforcing filler contains. 11. molding compound according to one of the preceding claims, characterized in that it further contains a flame-retardant additive. 809825/06 * 0