DE3117514A1 - Aromatic polyethers containing olefinic terminal groups - Google Patents

Aromatic polyethers containing olefinic terminal groups

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Publication number
DE3117514A1
DE3117514A1 DE19813117514 DE3117514A DE3117514A1 DE 3117514 A1 DE3117514 A1 DE 3117514A1 DE 19813117514 DE19813117514 DE 19813117514 DE 3117514 A DE3117514 A DE 3117514A DE 3117514 A1 DE3117514 A1 DE 3117514A1
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terminal groups
aromatic polyethers
aromatic
olefinic
polyethers
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Franz Dipl.-Chem. Dr. 6730 Neustadt Brandstetter
Juergen Dipl.-Chem. Dr. 6903 Neckargemünd-Dilsberg Hambrecht
Herbert Dipl.-Chem. Dr. 6719 Wattenheim Naarmann
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment
    • C08G65/485—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Polyphenylene ethers containing olefinic, polymerisable terminal groups, and the use of such polyphenylene ethers for the preparation of copolymers with other compounds containing polymerisable double bonds.

Description

Aromatische Polyether mit olefinischen EndgruppenAromatic polyethers with olefinic end groups

Die Erfindung betrifft aromatische Polyether mit olefinischen polymerisierbaren Endgruppen. The invention relates to aromatic polyethers with olefinic polymerizable End groups.

Aromatische Polyether mit olefinischen Gruppen sind beispielsweise in der DE-OS 29 17 819 (US-PS 4 207 406) beschrieben. Hierbei handelt es sich z.B. um Copolymerisate von 2,6-Dimethylphenol und 2-Allyl-6-methyl--phenol. Versucht man derartige Copolymerisate mit anderen copolymerisierbaren Monomeren zu polymeriseren, so können leicht vernetzte unlösliche Produkte entstehen, deren weitere Verarbeitung schwierig ist. Aromatic polyethers with olefinic groups are for example in DE-OS 29 17 819 (US-PS 4 207 406). These are e.g. to copolymers of 2,6-dimethylphenol and 2-allyl-6-methylphenol. Tries to polymerize such copolymers with other copolymerizable monomers, so slightly crosslinked insoluble products can arise, their further processing is difficult.

Außerdem sind acylgekoppelte Polymere von chinongekoppelten Polyphenylenoxiden bekannt, die unter anderem als Acylkomponente die Maleinsäure enthalten können (DE-OS 28 22 859 US-PS 4 156 77). Diese mit Maleinsäure gekoppelten Polyphenylenoxide sind aber z.B. nicht geeignet, mit anderen Doppelbindungen enthaltenden Monomeren zu copolymerisieren, so daß sie als Copolymerisationskomponenten nicht in Frage kommen. In addition, acyl-coupled polymers are quinone-coupled polyphenylene oxides known, which may contain maleic acid as an acyl component (DE-OS 28 22 859 U.S. Patent 4,156,77). These are maleic acid coupled polyphenylene oxides but e.g. not suitable to work with other monomers containing double bonds copolymerize, so that they are out of the question as copolymerization components.

Der vorliegenden Erfindung liegt die Aufgabe zugrunde, aromatische Polyether mit olefinischen, polymerisierbaren Endgruppen zu schaffen. The present invention is based on the object of aromatic To create polyethers with olefinic, polymerizable end groups.

Die Aufgabe wird erfindungsgemäß gelöst, durch aromatische Polyether, die eine olefinische Endgruppe der allgemeinen Formel enthalten wobei Wasserstoff oder ein aliphatischer Alkylrest sein kann.The object is achieved according to the invention by aromatic polyethers which contain an olefinic end group of the general formula where hydrogen or an aliphatic alkyl radical can be.

'Gegenstand der Erfindung sind daher Polyphenylenether des Patentanspruches 1.The invention therefore relates to the polyphenylene ethers of the patent claim 1.

Ein weiterer Gegenstand der Erfindung ist die Verwendung der olefinische Endgruppen enthaltenden Polyphenylenether nach Anspruch 1 zur Herstellung von Copolymerisaten mit anderen polymerisierbare Doppelbindungen enthaltenden Verbindungen. Another object of the invention is the use of the olefinic Polyphenylene ether containing end groups according to Claim 1 for the production of copolymers with other compounds containing polymerizable double bonds.

Unter aromatischen Polyethern werden Polyphenylenoxide verstanden, bei denen der Ethersauerstoff der einen Einheit an den aromatischen Ring der benachbarten Einheit gebunden ist. Bevorzugt handelt es sich bei den Polyethern um Verbindungen auf der Basis von in ortho-Position disubstituierten Polyphenylenoxiden. Dabei sollen mindestens 20 Einheiten miteinander verknüpft sein. Die Polyether können in ortho-Stellung zum Sauerstoff Wasserstoff, Halogen, Kohlenwasserstoffe, Halogenkohlenwasserstoffe, Phenylreste und Kohlenwasserstoff-oxi-Reste tragen. So kommen in Frage: Poly(2,6-dichlor-1,4-phenylen)-ether, Poly(2,6-diphenyl-1,4-phenylen)ether, Poly(2,6-dimethyl-1,4-phenylen)-ether, Poly(2,6-dibrom--1,4-phenylen)ether Derartige Polyether haben freie phenolische Hydroxylendgruppen. Aromatic polyethers are understood to mean polyphenylene oxides, in which the ether oxygen of one unit is attached to the aromatic ring of the neighboring Unity is bound. The polyethers are preferably compounds based on polyphenylene oxides disubstituted in the ortho position. This should at least 20 units must be linked together. The polyethers can be in the ortho position to oxygen hydrogen, halogen, hydrocarbons, halogenated hydrocarbons, Wear phenyl radicals and hydrocarbon-oxy radicals. So come into question: Poly (2,6-dichloro-1,4-phenylene) -ether, Poly (2,6-diphenyl-1,4-phenylene) ether, poly (2,6-dimethyl-1,4-phenylene) ether, poly (2,6-dibromo-1,4-phenylene) ether Such polyethers have free phenolic hydroxyl end groups.

Die aromatischen Polyether werden u.a. durch Selbstkondensation der entsprechend einwertigen Phenole durch Einwirken von Sauerstoff in Gegenwart eines Katalysatorsarstems, wie es beispielsweise in den US-PSen 3 219 625, 3 306 874, 3 306 875, 3 956 442, 3 965 o69, 3 972 851 beschrieben ist, hergestellt. The aromatic polyethers are produced, among other things, by self-condensation of the correspondingly monohydric phenols by the action of oxygen in the presence of a Catalyst systems, as described, for example, in US Pat. Nos. 3,219,625, 3,306,874, 3,306,875, 3,956,442, 3,965,069, 3,972,851.

Bei den olefinischen polymerisierbaren Endgruppen handelt es sich um eine vinylische bzw. allylische Gruppierung. Bevorzugt sind vinylische Endgruppen.The olefinic polymerizable end groups are a vinylic or allylic group. Vinylic end groups are preferred.

Die Herstellung der aromatischen Polyether mit olefinischer Endgruppe erfolgt u.a. durch die Umsetzung der freien phenolischen Hydroxylendgruppe mit einer Verbindung, die eine vinylische Endgruppe und eine mit der Hydroxylendgruppe des aromatischen Polyethers reagierende, zu einer Verknüpfung von Polyether und vinylischer Endgruppe tragenden Verbindung enthält. Beispielsweise kommen in Betracht eine olefinische Doppelbindung enthaltende Säurehalogenide, -anhydride bzw. -ester, Epoxide und Isocyanate. In Frage kommen beispielsweise: Acrylsäurechlorid, Methacrylsäurechlorid, Methacrylsäureanhydrid, p-Vinyl-benzoylchlorid, Vinylphosphonsäuredichlorid> Vinylsulfonsäurechlorid, Vinylisocyanat, Vinylchloriden. The production of aromatic polyethers with olefinic end groups takes place, among other things, by the reaction of the free phenolic hydroxyl end group with a Compound having one vinylic end group and one with the hydroxyl end group of the aromatic polyether reacting to a linkage of polyether and vinylic Contains end group bearing compound. For example, an olefinic one can be considered Acid halides, anhydrides or esters containing double bonds, epoxides and isocyanates. For example: acrylic acid chloride, methacrylic acid chloride, methacrylic anhydride, p-vinyl benzoyl chloride, vinyl phosphonic acid dichloride> vinyl sulfonic acid chloride, Vinyl isocyanate, vinyl chlorides.

Bevorzugt ist dabei Methylacrylsäurechiorid Vinylphosphonsäuredichlorid und Vinylphosphonsäurechlorid. Methylacrylic acid chloride vinyl phosphonic acid dichloride is preferred and vinyl phosphonic acid chloride.

Bevorzugt sind Polyphenylenether,-die eine olefinische Endgruppe der allgemeinen Formel enthalten worin R die oben angegebene Bedeutung hat und A folgende Gruppierung sein kann.Polyphenylene ethers which contain an olefinic end group of the general formula are preferred in which R has the meaning given above and A has the following grouping can be.

Die Umsetzung des aromatischen Polyethers mit diesen Verbindungen erfolgt bevorzugt in organischen Lösungsmitteln wie es beispielsweise in der Schrift "The chemistry of the hydroxyl group Part 1 S. 453 bis 503 (1971) Interscience Publishers Landon - New York -Sydney - Toronto - von S. Patai beschrieben ist. Die Reaktion kann dabei in Gegenwart von Katalysatoren wie tert. Amine oder sogenannten "Phasentransferkatalysatoren" wie quartären Ammonium-, Phosphonium-, Arsenium- und tertiären Sulfonium-Verbindungen erfolgen.The reaction of the aromatic polyether with these compounds preferably takes place in organic solvents such as, for example, in the scriptures "The chemistry of the hydroxyl group Part 1 pp. 453-503 (1971) Interscience Publishers Landon - New York - Sydney - Toronto - is described by S. Patai. The reaction can in the presence of catalysts such as tert. Amines or so-called "phase transfer catalysts" such as quaternary ammonium, phosphonium, arsenium and tertiary sulfonium compounds take place.

Die erfindungsgemäßen aromatischen Polyether können z.B. als Komponente für Mischungen mit anderen Polymeren wie Polystyrol, ABS verwendet werden. Insbesondere können die Polyether mit anderen doppelbindungshaltigen polymerisierbaren Verbindungen, wie beispielsweise Styrol, Acrylnitril, Methacrylsäuremethylester, Alkylester der Acrylsäure, Butadien, Isopren copolymerisiert werden. Es können aber auch Terpolymerisate hergestellt werden, die aus den aromatischen Polyethern mit olefinischer Doppelbindung und zwei weiteren doppelbindungshaltigen Verbindungen, wie beispielsweise Styrol/ Acrylnitril, Styrol/Maleinsäuranhydrid, Styrol/Butadien, Acrylnitril/Butadien aufgebaut sind. Solche Copolymerisate eignen sich z.B. als thermoplastische Kunststoffe oder in Kombination mit phosphonhaltigen Verbindungen zur Flammfestausrüstung von thermoplastischen Kunstst ffen.For example, the aromatic polyethers of the present invention can be used as a component can be used for blends with other polymers such as polystyrene, ABS. In particular the polyethers can be combined with other polymerizable compounds containing double bonds, such as styrene, acrylonitrile, methyl methacrylate, alkyl esters Acrylic acid, butadiene, isoprene can be copolymerized. However, terpolymers can also be used are made from the aromatic polyethers with an olefinic double bond and two other compounds containing double bonds, such as styrene / Acrylonitrile, styrene / maleic anhydride, styrene / butadiene, acrylonitrile / butadiene are. Such copolymers are suitable, for example, as thermoplastics or in combination with phosphone-containing compounds for the flame-retardant finishing of thermoplastics Plastic.

Die Erfindung wird anhand nachfolgender Beispiele erläutern. Die in den Beispielen angegebenen Anteile beziehen sich, wenn es nicht anders angegeben auf das Gewicht.The invention is illustrated by the following examples. In the The proportions given in the examples relate, unless otherwise stated on weight.

Beispiel 1 122 g Poly(2,6-dimethyl-1,4-phenylen)ether, der durch die Umsetzung von 2,6-Dimethylphenol in Toluol in Gegenwart von Cu-I-Br/Dibutylamin und Sauerstoff hergestellt wurde, mit einer Grenzviskosität von 0,48 dl/g (gemessen bei 300C in Chloroform) werden in 1100 g Toluol bei 8Q°C gelöst. Nach dem Abkühlen auf 23°C werden 55 g Dimethylformamid und 22 g Triethylamin zugegeben.Example 1 122 g of poly (2,6-dimethyl-1,4-phenylene) ether obtained by the Conversion of 2,6-dimethylphenol in toluene in the presence of Cu-I-Br / dibutylamine and oxygen was produced, with an intrinsic viscosity of 0.48 dl / g (measured at 300C in chloroform) are dissolved in 1100 g of toluene at 80C. After cooling down 55 g of dimethylformamide and 22 g of triethylamine are added to 23 ° C.

Dazu tropft man unter starkem Rühren und unter Stickstoff 160 g Vinylphosphonsäuredichlorid bei 2300. Bei dieser Temperatur wird nach der Zugabe des Vinylphosphonsäuredichlorid noch 2 Stunden gerührt, Man läßt noch 1 Stunde bei 80°C nachreagieren, kühlt auf Raumtemperatur ab und fällt in 5500 g Methanol aus. Nach dem grUndlichen Waschen mit Methanol bzw. Wasser wird bei 1 Torr im Vakuum bei 500C getrocknet. Das Produkt enthält nach Umfällen 0,25 Gew.-% P und 0,01 Doppelbindungen/100 g Polymerisat (iodometrische Titration nach Anlagerung von ICl3).160 g of vinylphosphonic acid dichloride are added dropwise with vigorous stirring and under nitrogen at 2300. At this temperature, after the addition of the vinylphosphonic acid dichloride Stirred for a further 2 hours, the reaction is allowed to continue for 1 hour at 80.degree. C., and the mixture is cooled Room temperature and precipitates in 5500 g of methanol. After thorough washing with methanol or water is dried at 1 Torr in vacuo at 50.degree. The product contains after reprecipitation 0.25 wt .-% P and 0.01 double bonds / 100 g polymer (iodometric Titration after the addition of ICl3).

Beispiel 2 100 g Poly(2,6-dimethyl-i,4-phenylen)ether, der durch Umsetzung von 2,6-Dimethylphenol in Toluol in Gegenwart von Cu-I-Br(Dibutylamin und Sauerstoff erhalten werde und eine Grenzviskosität von 0,32 dl/g (gemessen bei 30°C in Chloroform) werden in 1000 g Toluol bei 80°C gelöst. Nach dem Abkühlen auf 50°C werden unter starkem Rühren 1 g einer 50%igen wäßrigen Natriumhydroxidlösung und 0,01 g Tetrabutylammoniumbromid zur Lösung gegeben.Example 2 100 g of poly (2,6-dimethyl-1,4-phenylene) ether obtained by reaction of 2,6-dimethylphenol in toluene in the presence of Cu-I-Br (dibutylamine and oxygen and an intrinsic viscosity of 0.32 dl / g (measured at 30 ° C in chloroform) are dissolved in 1000 g of toluene at 80 ° C. After cooling to 50 ° C are under vigorous stirring 1 g of a 50% strength aqueous sodium hydroxide solution and 0.01 g of tetrabutylammonium bromide added to the solution.

Dazu tropft man im Verlaufe von 5 Minuten eine Lösung von 1,1 g Methacrylsäurechlorid und 0,02 g Di-tert.butylkresol in 10 ml Toluol unter heutigem Rühren bei 50°C.A solution of 1.1 g of methacrylic acid chloride is added dropwise over the course of 5 minutes and 0.02 g of di-tert-butyl cresol in 10 ml of toluene with current stirring at 50 ° C.

Nach weiteren 10 Minuten läßt man abkühlen, neutralisiert mit verdünnter Essigsäure> fällt in Methanol aus, fil- 9 triert ab, wäscht mit Methanol und trocknet im Vakuum bei 1 Torr und 500C. Das Produkt enthält 0,015 Doppelbindungen/100 g Polymerisat.After a further 10 minutes, the mixture is allowed to cool, neutralized with dilute Acetic acid> precipitates in methanol, fil- 9 wears off, washes with Methanol and dried in vacuo at 1 torr and 500C. The product contains 0.015 double bonds / 100 g polymer.

Beispiel 3 Die Reaktion wird analog Beispiel 2 durchgefUhrt nur, daß anstelle von MethacrylsSurechlorid, 6,3 g Vinylsulfonsäurechlorid verwendet werden. Das Produkt enthält 0,3 Gew.% S und 0,0094 Doppelbindungen/100 g Polymerisat.Example 3 The reaction is carried out as in Example 2 except that instead of methacrylic acid chloride, 6.3 g vinyl sulfonic acid chloride can be used. The product contains 0.3% by weight of S and 0.0094 double bonds / 100 g of polymer.

Beispiele 4-9 Die in Tabelle 1 angegebenen Mengen der erfindungsgemäßen Polyether aus den Beispielen 1 bis 3 werden in den in Tab. 1 angegebenen Mengen der Comonomeren und Obis 20 Gewichtsteilen Ethylbenzol gelöst und bei 140°C, 12 h in einer unter Stickstoff abgeschmolzenen Hochdruckglasampulle (Bombenrohr) polymerisiert. Das erhaltene Polymerisat wird bei 500C unter Vakuum vom Lösungsmittel und den Restmonomeren befreit. Die Zusammensetzung wird IR-spektroskopisch (Styrol) und mit Hilfe der Elementenanalyse (Acrylnitril bestimmt. Die Grenzviskosität wurde bei 300C in Chloroform gemessen.Examples 4-9 The amounts of the substances according to the invention given in Table 1 Polyethers from Examples 1 to 3 are used in the amounts given in Tab the comonomers and Obis 20 parts by weight of ethylbenzene dissolved and at 140 ° C, 12 h polymerized in a high pressure glass ampoule (bomb tube) melted under nitrogen. The polymer obtained is removed from the solvent and the residual monomers at 50 ° C. under vacuum freed. The composition is IR spectroscopic (styrene) and with the help of Elemental analysis (acrylonitrile determined. The intrinsic viscosity was measured at 30 ° C. in chloroform measured.

Die charakteristischen Daten der Copolymeren sind in Tab. 1 zusammengestellt.The characteristic data of the copolymers are compiled in Table 1.

Tabelle 1 Monomerenzusammensetzung Copolymerzusammen- Grenzviskosität Beispiel Polyether Comonomere Ethylbenzol setzung [Gew.%] (Gew.%) (Gew.%) (Gew.%) Styrol Acrylnitril [dl/g] 4 Beispiel 1 Styrol (54) (20) 68 20 0,53 (8) Acrylnitril (18) 5 Beispiel 1 Styrol (42) (20) 54 17 0,56 (24) Acrylnitril (14) 6 Beispiel 1 Styrol (30) (20) 38 10 0,58 (40) Acrylnitril (10) 7 Beispiel 2 Styrol (30) (20) 37 13 0,38 (40) Acrylnitril (10 8 Beispiel 3 Styrol (60) (0) 58 - 0,39 (40)Table 1 Monomer Composition, Copolymer Composition, Intrinsic Viscosity Example polyether comonomers ethylbenzene composition [% by weight] (% by weight) (% by weight) (% by weight) Styrene Acrylonitrile [dl / g] 4 Example 1 Styrene (54) (20) 68 20 0.53 (8) Acrylonitrile (18) 5 Example 1 Styrene (42) (20) 54 17 0.56 (24) Acrylonitrile (14) 6 Example 1 Styrene (30) (20) 38 10 0.58 (40) Acrylonitrile (10) 7 Example 2 Styrene (30) (20) 37 13 0.38 (40) acrylonitrile (10 8 Example 3 styrene (60) (0) 58 - 0.39 (40)

Claims (2)

Patent ansprüche 1. Polyphenylenether, dadurch gekennzeichnet, daß sie olefinische Endgruppen der allgemeinen Formel enthalten wobei R Wasserstoff oder ein aliphatischer Alkylrest sein kann.Claims 1. Polyphenylene ethers, characterized in that they contain olefinic end groups of the general formula where R can be hydrogen or an aliphatic alkyl radical. 2. Verwendung der olefinische Endgruppen enthaltenden Polyphenylenether zur Herstellung von Copolymerisaten mit anderen polymerisierbare Doppelbindungen enthaltenden Verbindungen.2. Use of the polyphenylene ethers containing olefinic end groups for the production of copolymers with other polymerizable double bonds containing compounds.
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WO1987000540A1 (en) * 1985-07-24 1987-01-29 General Electric Company Functionalized polyphenylene ethers and methods of preparation and use
EP0267382A1 (en) * 1986-09-29 1988-05-18 General Electric Company Functionalized polyphenylene ethers, method of preparation, and polyphenylene ether-polyamide compositions prepared therefrom
WO1988008433A1 (en) * 1987-04-24 1988-11-03 Allied-Signal Inc. Compositions of polyphenylene oxides and thermoplastic polymers
WO2001040354A1 (en) * 1999-12-01 2001-06-07 General Electric Company Poly(phenylene ether) - polyvinyl thermosetting resin
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EP0106023A2 (en) * 1982-06-30 1984-04-25 Amoco Corporation End-capped polyarylene polyethers, articles made therefrom and process for preparing such polyarylene polyethers
EP0106023A3 (en) * 1982-06-30 1985-09-25 Union Carbide Corporation End-capped polyaryl polyethers, articles made therefrom and process for preparing such polyarylene polyethers
WO1987000540A1 (en) * 1985-07-24 1987-01-29 General Electric Company Functionalized polyphenylene ethers and methods of preparation and use
JPS63500803A (en) * 1985-07-24 1988-03-24 ゼネラル・エレクトリック・カンパニイ Functionalized polyphenylene ethers and production methods and uses
EP0267382A1 (en) * 1986-09-29 1988-05-18 General Electric Company Functionalized polyphenylene ethers, method of preparation, and polyphenylene ether-polyamide compositions prepared therefrom
WO1988008433A1 (en) * 1987-04-24 1988-11-03 Allied-Signal Inc. Compositions of polyphenylene oxides and thermoplastic polymers
AU621052B2 (en) * 1987-04-24 1992-03-05 Allied-Signal Inc. Compositions of polyphenylene oxides and thermoplastic polymers
US8192649B2 (en) 1999-12-01 2012-06-05 Sabic Innovative Plastics Ip B.V. Capped poly(arylene ether) composition and method
EP1834975A1 (en) * 1999-12-01 2007-09-19 General Electric Company Poly(Phenylene ether) - Polyvinyl thermosetting resin
US6352782B2 (en) 1999-12-01 2002-03-05 General Electric Company Poly(phenylene ether)-polyvinyl thermosetting resin
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