WO1981002021A1 - Stabilisation de compositions d'ether de polyphenylene par des piperidines tetrasubstituees - Google Patents

Stabilisation de compositions d'ether de polyphenylene par des piperidines tetrasubstituees Download PDF

Info

Publication number
WO1981002021A1
WO1981002021A1 PCT/US1981/000041 US8100041W WO8102021A1 WO 1981002021 A1 WO1981002021 A1 WO 1981002021A1 US 8100041 W US8100041 W US 8100041W WO 8102021 A1 WO8102021 A1 WO 8102021A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
parts
acid
composition
weight
Prior art date
Application number
PCT/US1981/000041
Other languages
English (en)
Inventor
V Abolins
G Cooper
Original Assignee
Gen Electric
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gen Electric filed Critical Gen Electric
Priority to DE19813129766 priority Critical patent/DE3129766A1/de
Publication of WO1981002021A1 publication Critical patent/WO1981002021A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines

Definitions

  • polyphenylene ether resin is descriptive of a well known group of polymers that may be made by a variety of catalytic and non-catalytic processes.
  • certain of the polyphenylene ethers are disclosed in Hay, U.S. Patent No. 3,306,874 and 3,306,875, and in Stamatoff, 3,257,357 and 3,257,358,
  • the polyphenylene ethers are prepared by an oxidative couplingreaction coroprising passing an oxygen-containing gas through a reaction solution of a phenol and a metal-amine complex catalyst.
  • the polyphenylene ethers are produced by reacting the corresponding phenolate ion with an initiator, such as a peroxy acid salt, an acid peroxide, a hypophalite, and the like, in the presence of a complexing agent. Disclosures relating to non-catalytic processes, such as oxidation with lead dioxide, silver oxide, etc., are described in Price et al, U.S.
  • Hydroxybenzophenones and hydroxybenzotriazoles in combination with organic nickel complexes have been utilized in stabilizing polyphenylene ether compositions against ultraviolet light instability. It has been found that a tetrasubstituted piperidine is a very effective agent for preventing the ultraviolet light induced discoloration of polyphenylene ether resin compositions. This stabilizer also imparts thermal stability and can be used alone or in combination with a phosphite or a hydroxybenzotriazole or a hindered phenolic antioxidant.
  • the tetrasubstituted piperidines have been used in the prior art as an ultraviolet stabilizer for polystyrene, polyolefins polyurethanes and for segmented copolyesters.
  • this stabilizer in combination with a 2- (2H-benzotriazol-2-yl)-p-cresol has been used in the prior art for stabilizing polyolefins and polystyrene.
  • An advantage attributed to the use of the tetrasubstituted piperidine stabilizer is that it produces no change in initial color of polyphenylene ethers which has resulted from stabilizers such as the organic nickel complexes.
  • R 1 and R 2 which may be the same of different, each are an alkyl group, or they form, together with the carbon atom to which they are attached, a saturated alicyclic group with 5 to 7 ring carbon atoms or a group of the formula:
  • n is an integer of 1 to 3 inclusive; and when n is 1, R 3 is an acyl group, an N-substituted carbamoyl group having as a substituent alkyl, cycloalkyl or aryl, an N-Monosubstituted thiocarbamoyl group having as a substituent alkyl, cycloalkyl or aryl, a monovalent group obtained by removing a hydroxyl group from a sulfinic acid, a sulfonic acid, a phosphorus-containing acid or a boric acid, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group or a group of the general formula:
  • R 3 is a diacyl, derived from a dibasic aliphatic or aromatic carboxylic acid, a dicarbamoyl group in which two carbamoyl groups are combined by interruption of aryl, alkyl, diarylalkane or diaryl ether, a carbonyl group, a divalent group obtained by removing two hydroxyl groups from a disulfonic acid, a phosphorus-containing acid or a boric acid, an alkylene group, an arylene group or arylene dialkylene group, and when n is 3, R 3 is a triacyl group derived from an aromatic, cycloaliphatic or furane tricarboxylic acid, a tricarbamoyl group in which three carbamoyl groups are attached to one aryl group, a trivalent group obtained by removing three hydroxyl groups from a trisulfonic acid, a phosphorus-containing acid or
  • the polyphenylene ether resins comprise polymers of structural units of the formula:
  • Q is selected from the group consisting of hydrogen, hydrocarbon radicals, halohydrocarbon radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus, hydrocarbonoxy radicals and halohydrocarbonoxy radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus, Q' and Q" are the same as Q and in addition halogen, with the proviso that Q and Q' are both free of a tertiary carbon atom and n is an integer of at least 50.
  • the preferred polyphenylene ether resin is a poly (2 , 6-dimethyl-1,4-phenylene) ether resin having an intrinsic viscosity of from about 0.4 to about 0.65 dl/g as measured in chloroform at 30°C.
  • the vinyl aromatic resin will have at least 25% of units derived from monomers of the formula:
  • R 1 and R 2 are selected from the group consisting of lower alkenyl groups of from 1 to 6 carbon atoms and hydrogen;
  • R 3 , R 4 and R 5 are selected from the group consisting of chloro, bromo, hydrogen and (lower) alkyl of from 1 to 6 carbon atoms;
  • R 6 and R 7 are selected from the group consisting of hydrogen and (lower) alkyl and alkenyl group of from 1 to 6 carbon atoms or R 6 and R 7 may be concatenated together with hydrocarbyl groups to form a naphthyl group.
  • Styrene is the preferred vinyl aromatic compound.
  • An ⁇ , ⁇ -unsaturated cyclic anhydride may be copolymerized with the vinyl aromatic compound. These compounds may be represented by the formula :
  • R 9 is selected from the group consisting of hydrogen, vinyl, alkenyl alkylcarboxylic or alkenylcarboxylic of from 1 to 12 carbon atoms, n is 1 or 2, depending on the position of the carbon-carbon double bond, and m is an integer of from 0 to about 10. Examples include maleic anhydride, citraconic anhydride, itaconic anhydride, aconitic anhydride and the like.
  • Rubber i.e. 1-15 parts by weight may be employed in preparing the rubber-modified polymers of a vinyl aromatic compound such as polybutadiene rubber, butyl rubber, styrenebutadiene rubber, acrylonitrile rubber, ethylene-propylene copolymers, natural rubber, EPDM rubbers, and the like.
  • thermoplastic rubbers such as the AB or ABA block copolymers may be used at 1-15 parts by weight of composition.
  • Suitable ABA block copolymers are the Kraton or Kraton G polymers that are described in U.S. 3,646,162 and U.S. 3,595,942, respectively, both of which patents are incorporated by reference.
  • the vinyl aromatic resin can comprise from 40 to 0 parts by weight of the ⁇ , ⁇ nnsaturated cyclic anhydride, from 60 to 100 parts by weight of a vinyl aromatic compound and from 1 to 25 parts by weight of rubber.
  • the preferred copolymers will comprise from about 85 to 95 parts by weight of the vinyl aromatic compound and about 10 parts by weight of the rubber.
  • a preferred vinyl aromatic polymer is rubber modified, high impact polystyrene.
  • a preferred rubber modified vinyl aromatic ⁇ , ⁇ -unsaturated cyclic anhydride copolymer is Dylark 240, available from Arco Polymers, Dylark 240 is a high impact styrene maleic anhydride copolymer containing 9-10% rubber, 9% maleic anhydride, and the balance being styrene.
  • a preferred class of tetrasubstituted piperidines are the mono or di-acyl esters such as the benzoate, adipate and most preferably the sebacic acid diester of 2 , 2,6, 6-tetramethyl-4- hydroxypiperidine.
  • compositions may comprise from 15 to 95 parts by weight of a polyphenylene ether resin from 85 to 5 parts by weight of a vinyl aromatic resin; from 0.05 to 5.0 parts by weight and more preferably 0.1 to 0.5 parts by weight of the tetrasubstituted piperidine and optionally from 0.1 to 5.0 parts by weight of the hydroxybenzotriazole and optionally 0.25 to 1.5 parts of a phosphite ester or 0.1 to 0.5 parts of a hindered phenolic an oxidant.
  • the polyphenylene ether resin may comprise 60 to 99 parts by weight; from 0.1 to 5.0 parts by weight of tetrasubstituted piperidine; from 0.5 to 2 parts by weight of a phosphite compound; from 0-15 parts by weight of a thermoplastic rubber; 0 to 30 parts by weight of a phosphate plasticizer.
  • the useful hydroxybenzotriazoles include 2- (2H-benzotriazol-2-yl)-p-cresol; 2- (2H-benzotriazol-2-yl)-4,6-di-tertpentylphenol; 2-tert-butyl-6- (5-chloro-2H-benzotriazol-2-yl) pcresol; 2 ,4-di-tert-butyl-6- (5chloro-2H-benzotriazol-2-yl) phenol.
  • Other compounds of this type may be found in U.S. 3,004,896 which is hereby incorporated by reference.
  • the phosphite esters have the structure P (OR) 3 wherein R is phenyl or an alkyl group of 6-12 carbon atoms such as hexyl, nonyl, decyl or dodecyl. They are described in 3,969,306.
  • hindered phenol is used to describe a compound having at least one phenolic hydroxyl group which has di-ortho substituted alkyl groups such as tert-butyl groups. Examples of these compounds are 2 , 6-di-tert-butyl-p-cresol; 2,2'methylenebis
  • phosphate plasticizers are the phosphates described in U.S. 4,077,934 which is incorporated by reference.
  • compositions of this invention may also include amounts of fillers such as from 1-40 parts by weight of a reinforcing filler such as filamentous glass or other fillers such as quartz, metal fibers, wollastonite or the fillers mentioned in U.S. 4,080,351, columns 3 and 4 which is hereby incorporated by reference.
  • a reinforcing filler such as filamentous glass or other fillers such as quartz, metal fibers, wollastonite or the fillers mentioned in U.S. 4,080,351, columns 3 and 4 which is hereby incorporated by reference.
  • flame retardants may be added in a minor proportion to impart flame retardant properties to the compositions. Flame retardants such as those described in U.S. 3,833,535, which is incorporated by reference may be utilized in the compositions of the invention.
  • the composition may be prepared by tumbling powdered forms of the components, extruding the mixed powders into a continuous strand, chopping the strands into pellets and thereafter molding the pellets into the desired shape. These techniques are well known and do not form a part of the invention. All references to parts refer to parts by weight-
  • the molded plates were placed in racks on a rotating platform protected by a single thickness (0.090 inches) of ordinary window glass and exposed at a distance of three inches to a battery of fluorescent blacklight lamps. Yellowness index was measured each day according to the procedure of ASTM Test No. D1925 and the time re ⁇ uired for an increase of one yellowness unit was .estimated from a graph of the data obtained.
  • the control blend, without stabilizer, increased one unit in 36 days; the blend containing 0.5 phr of the sebacic acid diester required 61 days to increase by one unit of yellowness. It is believed that the mild extrusion conditions and the absence of vacuum contributed to the stability.
  • a control blend was extruded and molded, as described in Example 1, from 300 g of poly (2,6-dimethyl-1,4-phenylene) ether, 300 g of polystyrene, 6 g of tridecyl phosphite, 18 g of triphenyl phosphate, 9 g of low molecular weight polyethylene , 0.9 g of zinc sulfide, 0.9 g of zinc oxide, and 18 g of titanium dioxide.
  • a control blend containing 585 g of poly (2,6-dimethyl- 1.4-phenylene) ether, 165 g of triphenyl phosphate, and 22.5 g of titanium dioxide was extruded and molded as described in Example 1.
  • a second blend was similarly prepared, with the addition of 3 g of the sebacic acid diester of Example 1.
  • a third blend was prepared from 585 g of poly (2,6-dimethyl-l,4-phenylene) ether, 165 g of triphenyl phosphate, 6 g of tridecyl phosphite, and 22.5 of titanium dioxide, and a fourth having the same composition as the third, with the addition of 3 g of the sebacic acid diester of Example 1.
  • the plates were exposed under the conditions described in Example 1;
  • 500 g of poly (2,6-dimethyl-1,4-phenylene) ether, 500 g of rubber modified high impact* polystyrene, 10 g tridecyl phosphite, 15 g of polyethylene, 30 g of triphenyl phosphate, 1.5 g of zinc fulfide, 1.5 g of zinc oxide, and 30 g of titanium dioxide were blended and extruded as described in Example 1, except that a vacuum of 25 inches of mercury was applied to the extruder vent.
  • Example 6 100 parts of the base composition of Example 5, 5 parts of titanium dioxide; 0.5 parts of hindered phenolic antioxidant* and varying amounts of stabilizers was extruded, molded, and tested as described in Example 5 , with the results shown in Table 2.
  • a mixture of 2.5 parts of a mixture of the sebacic acid diester of Example 1 with 2.5 parts of either 2- (2H-benzo- triazol-2-yl)-jo-cresol or 2- (2H-benzotriazol-2-yl)4,6-di-tert- pentylphenol delayed the onset of yellowing substantially longer than five parts of any of the stabilizers alone and the increase in yellowness after 15 days in the blend containing mixtures of stabilizers was less than half that of blends containing a single stabilizer.
  • Blends of 50 parts of the base composition of Example 5, 50 parts styrene-maleic acid copolymer*, 4 parts hydrogenated styrene-butadiene triblock copolymer**, 5 parts titanium dioxide, 0.5 parts of hindered phenolic antioxidant***, and varying amounts of light stabilizers were extruded, molded and tested as described in Example 5, with the results in Table 3.
  • Mixtures of the sebacic acid diester of Example 1 with either 2-(2H-benzo triazol-2-yl) -p-cresol or 2- (2H-benzotriazol-2-yl) 4 , 6-di-tert- pentylphenol were more effective than the some total amount of either stabilizer alone.
  • Example 8 A mixture of 55 parts of poly (2,6-dimethyl-1,4- phenylene) ether resin having an IV of about 0.5 dl/g as measured in CHC1 3 at 30°C; 45 parts of rubber modified, high impact polystyrene (Amoco 6H6) : 3.5 parts of the tri-arylphosphate used in Example 5; 1 part of diphenyl decyl phosphite; 1.5 parts of polyethylene; and 3 parts of titanium dioxide was extruded in a twin-screw extruder and the extruded pellets were then molded into standard test pieces in a screw injection molding machine.
  • Poly (2,6-dimethyl-1,4- phenylene) ether resin having an IV of about 0.5 dl/g as measured in CHC1 3 at 30°C
  • Amoco 6H6 rubber modified, high impact polystyrene
  • An additional stabilized composition was prepared which included 0.2 parts of the sebacic acid diester and 0.2 parts of octadecyl-3-
  • control composition embrittled in 31-35 days at 115°C while the stabilized composition remained ductile for 54-57 days.
  • compositions were prepared as described in Example 9 except that an EPDM modified polystyrene (12% Epcar EPDM rubber) was substituted for the butadiene modified polystyrene of Example 9.
  • EPDM modified polystyrene 12% Epcar EPDM rubber
  • a resin composition containing 50 parts of poly (2,6- dimethyl-1,4-phenylene) ether; 50 parts of rubber modified, high impact polystyrene; 1.5 parts polyethylene; 3 parts triphenylphosphate; 0.15 parts zinc sulfide and 0.15 parts zinc oxides were extruded and molded as described in Example 9. Compositions were prepared using this resin composition with the addition of the listed stabilizers and these compositions were aged in air at 115°C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Nouvelles compositions stabilisees d'ethers de polyphenylene basees sur l'utilisation de piperidine tetrasubstituee ou en combinaison avec un phosphite ou un hydroxybenzotriazol ou un phenol masque.
PCT/US1981/000041 1980-01-14 1981-01-13 Stabilisation de compositions d'ether de polyphenylene par des piperidines tetrasubstituees WO1981002021A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19813129766 DE3129766A1 (de) 1980-01-14 1981-01-13 Stabilization of polyphenylene ether-compositions by tetrasubstituted piperidines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11198480A 1980-01-14 1980-01-14
US111984 1987-10-22

Publications (1)

Publication Number Publication Date
WO1981002021A1 true WO1981002021A1 (fr) 1981-07-23

Family

ID=22341503

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1981/000041 WO1981002021A1 (fr) 1980-01-14 1981-01-13 Stabilisation de compositions d'ether de polyphenylene par des piperidines tetrasubstituees

Country Status (2)

Country Link
JP (1) JPS56501881A (fr)
WO (1) WO1981002021A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0073386A1 (fr) * 1981-08-20 1983-03-09 ADEKA ARGUS CHEMICAL CO., Ltd. Compositions de résines synthétiques contenant des éthers de 2,2,6,6-tétraméthylpipéridyle
EP0146878A2 (fr) * 1983-12-22 1985-07-03 General Electric Company Compositions de résines de polyéther de phénylène et de résines de polystyrène à haute résistance au choc à stabilité améliorée à la lumière ultraviolette
EP0149454A2 (fr) * 1984-01-13 1985-07-24 General Electric Company Compositions de résines de poly(éther de phénylène) et de résines de polystyrène à haute résistance au choc ayant une stabilité contre la lumière ultraviolette améliorée
EP0149781A1 (fr) * 1983-12-15 1985-07-31 BASF Aktiengesellschaft Dérivés de l'acide furanne-3-carboxylique
US5004759A (en) * 1986-02-14 1991-04-02 Ciba-Geigy Corporation Stabilisation of polyphenylene ethers with macrocyclic polyalkylpiperidine compounds
US5045578A (en) * 1987-10-16 1991-09-03 General Electric Co. Polymer mixture comprising polyphenylene ether, sterically hindered amine and epoxy compound and articles manufactured therefrom
US5210119A (en) * 1987-10-16 1993-05-11 General Electric Company Polymer mixture comprising polyphenylene ether, sterically hindered amine and epoxy compound and articles manufactured therefrom
US5382613A (en) * 1990-05-16 1995-01-17 Hoechst Ag Light-stable polyphenylene ether molding composition with an antistatic finish
US6479572B1 (en) 1996-11-15 2002-11-12 Basf Aktiengesellschaft Thermoplastic molding materials stable to thermal oxidation

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3639506A (en) * 1969-05-21 1972-02-01 Gen Electric Flame retardant composition of polyphenylene ether styrene resin aromatic phosphate and aromatic halogen compound
US3639334A (en) * 1965-01-13 1972-02-01 Gen Electric Stabilization of polyphenylene ethers
US3640928A (en) * 1968-06-12 1972-02-08 Sankyo Co Stabilization of synthetic polymers
US3761541A (en) * 1971-10-12 1973-09-25 Gen Electric Stabilized polyphenylene ethers
US4075165A (en) * 1975-05-28 1978-02-21 Ciba-Geigy Corporation Stabilization of polymers by penta- or hexa-substituted 4-piperidinol derivatives
US4131598A (en) * 1976-03-29 1978-12-26 General Electric Company Polyphenylene ether composition
US4140673A (en) * 1976-03-23 1979-02-20 Bayer Aktiengesellschaft Piperidine derivatives as light stabilizers

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH589056A5 (fr) * 1973-12-10 1977-06-30 Ciba Geigy Ag
US3925509A (en) * 1973-12-26 1975-12-09 Gen Electric Light stabilized polyphenylene ether resin composition
SE7415683L (fr) * 1973-12-28 1975-06-30 Ciba Geigy Ag
JPS5133938A (ja) * 1974-09-18 1976-03-23 Hitachi Ltd Hyojisochi

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3639334A (en) * 1965-01-13 1972-02-01 Gen Electric Stabilization of polyphenylene ethers
US3640928A (en) * 1968-06-12 1972-02-08 Sankyo Co Stabilization of synthetic polymers
US3639506A (en) * 1969-05-21 1972-02-01 Gen Electric Flame retardant composition of polyphenylene ether styrene resin aromatic phosphate and aromatic halogen compound
US3761541A (en) * 1971-10-12 1973-09-25 Gen Electric Stabilized polyphenylene ethers
US4075165A (en) * 1975-05-28 1978-02-21 Ciba-Geigy Corporation Stabilization of polymers by penta- or hexa-substituted 4-piperidinol derivatives
US4140673A (en) * 1976-03-23 1979-02-20 Bayer Aktiengesellschaft Piperidine derivatives as light stabilizers
US4131598A (en) * 1976-03-29 1978-12-26 General Electric Company Polyphenylene ether composition

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0073386A1 (fr) * 1981-08-20 1983-03-09 ADEKA ARGUS CHEMICAL CO., Ltd. Compositions de résines synthétiques contenant des éthers de 2,2,6,6-tétraméthylpipéridyle
EP0149781A1 (fr) * 1983-12-15 1985-07-31 BASF Aktiengesellschaft Dérivés de l'acide furanne-3-carboxylique
US4603205A (en) * 1983-12-15 1986-07-29 Basf Aktiengesellschaft Furan-3-carboxylic acid derivatives
EP0146878A2 (fr) * 1983-12-22 1985-07-03 General Electric Company Compositions de résines de polyéther de phénylène et de résines de polystyrène à haute résistance au choc à stabilité améliorée à la lumière ultraviolette
EP0146878A3 (en) * 1983-12-22 1985-11-13 General Electric Company Compositions of polyphenylene ether resin and high impact polystyrene resin having improved ultraviolet light resistance
EP0149454A2 (fr) * 1984-01-13 1985-07-24 General Electric Company Compositions de résines de poly(éther de phénylène) et de résines de polystyrène à haute résistance au choc ayant une stabilité contre la lumière ultraviolette améliorée
EP0149454A3 (en) * 1984-01-13 1986-01-22 General Electric Company Compositions of polyphenylene ether resin and high impact polystyrene resin having improved ultraviolet light resistance
US5004759A (en) * 1986-02-14 1991-04-02 Ciba-Geigy Corporation Stabilisation of polyphenylene ethers with macrocyclic polyalkylpiperidine compounds
US5045578A (en) * 1987-10-16 1991-09-03 General Electric Co. Polymer mixture comprising polyphenylene ether, sterically hindered amine and epoxy compound and articles manufactured therefrom
US5210119A (en) * 1987-10-16 1993-05-11 General Electric Company Polymer mixture comprising polyphenylene ether, sterically hindered amine and epoxy compound and articles manufactured therefrom
US5382613A (en) * 1990-05-16 1995-01-17 Hoechst Ag Light-stable polyphenylene ether molding composition with an antistatic finish
US6479572B1 (en) 1996-11-15 2002-11-12 Basf Aktiengesellschaft Thermoplastic molding materials stable to thermal oxidation

Also Published As

Publication number Publication date
JPS56501881A (fr) 1981-12-24

Similar Documents

Publication Publication Date Title
US4341879A (en) Polyphenylene ether resin composition having improved heat stability and impact strength
EP0413972B1 (fr) Compositions thermoplastiques contenant des polyoléfines et des polyéthers de phenylène et les articles à partir de celles-ci
US4077934A (en) Method of preparing compositions that comprise a polyphenylene ether resin and an alkenyl aromatic resin
US4405739A (en) Polyphenylene ether resins and compositions heat stabilized with phosphite compounds
EP0401690A2 (fr) Composition de poly(éther de phénylène) ayant une fluidité à l'état fondu améliorée
US4410651A (en) Impact resistant polyphenylene ether resin compositions
US4684682A (en) Flame retardant flexibilized polyphenylene ether compositions
US5973041A (en) Resinous compositions containing aromatic bisphosphoramidates as flame retardants
WO1981002021A1 (fr) Stabilisation de compositions d'ether de polyphenylene par des piperidines tetrasubstituees
US4123474A (en) Polyphenylene ether resin compositions containing a diphenylamine
US3956423A (en) Polyphenylene ethers composition containing N,N'-di-β-naphthyl-P-phenylene diamine stabilizer
US4532306A (en) Polyphenylene ether resin composition
US4373045A (en) Polyphenylene ether molding compositions that include an alkenyl aromatic resin, an ethylene propylene rubber and a triaryl phosphate
EP0417510A1 (fr) Composition d'éther de polyphenylène à flux amélioré
US4002701A (en) Polyphenylene ether resin compositions containing an N-alkanoyl-p-aminophenol stabilizer
JPS5928349B2 (ja) 樹脂用安定剤
US4427814A (en) Polyphenylene ether resin composition having improved heat stability
US4483953A (en) Polyphenylene ether resins and compositions heat stabilized with trineopentylene diphosphite
US4472546A (en) Polyphenylene ether resin composition
US5594054A (en) Flame retardant flexibilized polyphenylene ether compositions
GB2076831A (en) Compositions of a polyphenylene ether resin and a copolymer of styrene and bromostyrene
JP3142885B2 (ja) ポリフェニレンエーテル系樹脂組成物
US4073765A (en) Filled polyphenylene ether compositions having improved toughness
EP0086947A1 (fr) Composition de PPE contenant un modificateur de résistance au choc, agent ignifugeant/plastifiant et un reducteur de la viscosité fondue
US6579925B1 (en) Poly(arylene ether)-polystyrene composition

Legal Events

Date Code Title Description
AK Designated states

Designated state(s): DE JP

RET De translation (de og part 6b)

Ref document number: 3129766

Country of ref document: DE

Date of ref document: 19820401

WWE Wipo information: entry into national phase

Ref document number: 3129766

Country of ref document: DE