New! View global litigation for patent families

DE4103140A1 - Macro-monomer(s) for prepn. of graft copolymers - partic. omega-(vinyl:benzoyl)-poly-(2,6-di:methyl)-1,4-phenylene] ethers] - Google Patents

Macro-monomer(s) for prepn. of graft copolymers - partic. omega-(vinyl:benzoyl)-poly-(2,6-di:methyl)-1,4-phenylene] ethers]

Info

Publication number
DE4103140A1
DE4103140A1 DE19914103140 DE4103140A DE4103140A1 DE 4103140 A1 DE4103140 A1 DE 4103140A1 DE 19914103140 DE19914103140 DE 19914103140 DE 4103140 A DE4103140 A DE 4103140A DE 4103140 A1 DE4103140 A1 DE 4103140A1
Authority
DE
Grant status
Application
Patent type
Prior art keywords
deg
ppe
phenylene
ether
poly
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
DE19914103140
Other languages
German (de)
Inventor
Klaus Dr Muehlbach
Friedrich Dr Seitz
Michael Wicker
Walter Prof Dr Heitz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02Monomers containing only one unsaturated aliphatic radical
    • C08F12/04Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/22Oxygen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48Polymers modified by chemical after-treatment
    • C08G65/485Polyphenylene oxides

Abstract

Macromonomers of formula (I) are new., where R1, R2 are lower alkyl; R3 is H or lower alkyl; and n is polymerisation deg. of at least 5. Macromonomers of formula (Ia), partic. omega-(4-vinyl-)benzoyl-poly 2,6-dimethyl-1,4 phenylene ether (VB-PPE) of polymerisation deg. of the phenylene ether of 5-200 are specifically claimed. In (Ia), n = 5-200. USE/ADVANTAGE - Used for the prepn. of copolymers (claimed). Avoids prior art problems of sepg. copolymers and unreacted monomer. The graft polymers obtd. are useful as adhesives, compatabilisers in polymer alloys or rubber in materials. In an example, 30g poly-(2,6-dimethyl-1,4-phenylene ether) (PPE) (prepd. from p-chloro-2,6-dimethyl phenol) (Mn 13400) was dissolved in 350g pyridine. 10 mols. 4-vinyl benzoyl chloride were added at 0. deg. C, giving VB-PPE after 24 hrs.. 3g VB-PPE and 7g ethyl acrylate were dissolved in 50g toluene, 0.03 AIBN added and polymerisation occurred at 60 deg. C for 30 hrs.. The polymer was pptd. in 4 pts. vol. petroleum ether and 1 pt. vol. methanol and dried. The yield was 88%.

Description

Die Auffindung von Polymeren mit speziellen Strukturen und Eigenschaften ist eine zentrale Aufgabe der Forschung. The discovery of polymers with specific structures and properties is a central object of the research. Die Herstellung von Copolymeren durch Pfropfung unter Einsatz von Makromonomeren hat sich dabei zu einem effektiven Syntheseweg entwickelt. The preparation of copolymers by grafting using macromonomers has thereby developed into an effective synthetic route. Makromonomere sind Polymere mit einer polymerisationsfähigen Endgruppe; Macromonomers are polymers having a polymerizable terminal group; sie können Molekulargewichte von einigen Hundert bis zu mehreren Tausend haben. they can have molecular weights of a few hundred to several thousand.

Die Makromonomeren lassen sich aufgrund der polymerisierbaren Endgruppe sowohl homo- als auch copolymerisieren. The macromonomer can be both homo- and copolymerize due to the polymerizable end group. Durch Copolymerisation mit ge eigneten Comonomeren lassen sich Pfropfcopolymere herstellen, deren Haupt kette aus dem Comonomeren und der Endgruppe des Makromonomeren besteht. By copolymerization with suitable comonomers ge graft copolymers can be prepared, the main chain of the comonomers and the end group of the macromonomer exist. Die Seitenäste werden aus dem Strukturelement des Makromonomeren gebildet. The side branches are formed from the structural element of the macromonomers.

Makromonomere auf der Grundlage von Poly-(2,6-dimethyl-1,4-phenylenether) mit etherartig verknüpfter Vinylbenzylendgruppe werden von Percec (J. Polym. Sci., Part A, Polym. Chem. 25, 2605 (1987)) beschrieben. Macromonomers based on poly (2,6-dimethyl-1,4-phenylene ether) with ether-linked Vinylbenzylendgruppe be of Percec (J. Polym. Sci., Part A, Polym. Chem 25th 2605 (1987)) described , Es sind wohldefinierte Makromonomere. There are well-defined macromonomers. Es zeigt sich jedoch, daß die Copoly merisation dieser Makromonomeren unter Umständen zu einem unvollständigen Einbau der Makromonomeren führt. It appears, however, that the copoly leads polymerization of macromonomers may be an incomplete installation of the macromonomers. Dies wird insbesondere dann beobachtet, wenn das Molekulargewicht des Makromonomeren hoch ist. This is observed in particular when the molecular weight of the macromonomer is high. Der unvollständige Einbau führt zu uneinheitlichen Pfropfcopolymeren. The incomplete installation leads to non-uniform graft. Eine spätere Trennung von Pfropfcopolymer und nicht umgesetztem Makromonomer ist nicht möglich. A subsequent separation of the graft copolymer and unreacted macromonomer is not possible.

Es bestand somit die Aufgabe, Makromonomere auf der Grundlage von Poly 30 (2,6-dimethyl-1,4-phenylenether) zu schaffen, die sich durch Copolymeri sation vollständig in das Pfropfcopolymerisat überführen lassen. There was thus the object of macromonomers based on poly to provide 30 (2,6-dimethyl-1,4-phenylene ether), which can be completely converted by sation copolymerized in the graft copolymer.

Unmittelbarer Erfindungsgegenstand sind neue Makromonomere der allgemeinen Formel I The immediate subject invention are novel macromonomers of the general formula I

in der R 1 und R 2 Niederalkyl und R 3 Wasserstoff oder Niederalkyl und n einen Polymerisationsgrad von mindestens 5 bedeutet. in which R 1 and R 2 is lower alkyl and R 3 is hydrogen or lower alkyl and n is a degree of polymerization of at least. 5

Bevorzugt sind Makromonomere der allgemeinen Formel Ia Preferably the macromonomers of the general formula Ia

mit n=5 bis 200. with n = 5 to 200 microns.

Besonders bevorzugt ist ω-(4-Vinyl-)benzoyl-poly-(2,6-dimethyl-1,4- phenylenether) mit einem Polymerisationsgrad des Phenylenethers von 5 bis 200. Particularly preferred is ω- (4-vinyl) benzoyl-poly (2,6-dimethyl-1,4-phenylene ether) having a degree of polymerization of the phenylene ether of 5 to 200.

Die Herstellung der erfindungsgemäßen Makromonomeren geschieht am ein fachsten dadurch, daß man zunächst in bekannter Weise einen Polyphenylen ether (PPE) geeigneten Molgewichts von z. The preparation of the macromonomers according to the invention is done on a simplest characterized in that firstly a polyphenylene ether in a known manner (PPE) suitable molecular weight of z. B. etwa 500 bis 20 000 herstellt und dann dessen phenolische Endgruppe mit Hilfe eines Vinylbenzoyl halogenids verestert. For example, about 500 to 20 000 establishes then esterified the phenolic terminal group with the aid of a vinylbenzoyl halide.

Der benötigte Polyphenylenether wird z. The polyphenylene ether is needed for. B. nach den Angaben in einer der US-Patentschriften 36 61 848, 32 19 625, 33 78 505, 33 06 874, 33 06 875 und 36 39 656 oder nach dem Verfahren ausgehend von 2,6-Dimethylphenolen, die in 4-Stellung ein Halogenatom tragen (vgl. W. Risse et al., Makromol. Chem. 186, 1835 (1985) oder V. Percec et al., J.Poly.Sci., Polym. Lett. Ed. 24, 439 (1986)) gewonnen. B. according to the information in one of the US Patents 36 61 848, 32 19 625, 33 78 505 33 06 874, 33 06 875 and 36 39 656 or according to the process starting from 2,6-dimethyl phenols, in the 4- position a halogen atom wear al (see FIG. W. Risse et., Makromol. Chem. 186, 1835 (1985) or V. Percec et al., J.Poly.Sci., Polym. Lett. Ed. 24, 439 (1986 won)).

Die Umsetzung zum erfindungsgemäßen Makromonomeren wird wie üblich in Gegenwart bzw. mit Hilfe eines säurebindenden Mittels bewerkstelligt; The reaction to form the macromonomer according to the invention is, as usual, accomplished in the presence or with the aid of an acid binding agent; geeignet sind insbesondere organische Basen, die sich auch als Lösungs mittel eignen wie Pyridin oder Basen, die in einem Lösungsmittel für PPE (aromatische und/oder halogenierte nichtaromatische Kohlenwasserstoffe, Ether) wie Toluol, Xylol, Dichlormethan, THF ihrerseits löslich sind. Particularly suitable are organic bases, which compositions are suitable as a solvent such as pyridine or bases in a solvent for PPE (aromatic and / or halogenated non-aromatic hydrocarbons, ethers) are as toluene, xylene, dichloromethane, THF turn soluble.

Auch suspendierbare anorganische Basen oder Salze wie (Erd)alkalicarbonate sind verwendbar. Also suspendable inorganic bases or salts such as (earth) alkali metal carbonates are also usable.

Die Verwendung der Makromonomeren zur Polymerisation folgt den üblichen Regeln z. The use of the macromonomers follows the usual rules for the polymerization z. B. für die radikalisch ausgelöste Polymerisation: For example, for the free-radically initiated polymerization:

Zur Herstellung wohldefinierter Pfropfcopolymerer wird das Makromonomere mit geeigneten Comonomeren copolymerisiert. To produce well-defined graft copolymers the macromonomer is copolymerized with suitable comonomers. Das Gewichtsverhältnis von Makromonomer zu Comonomer kann beliebig sein und z. The weight ratio of macromonomer to the comonomer may be arbitrary and z. B. 1 : 99 bis 99 : 1, vor zugsweise von 1 : 99 bis 75 : 25 und insbesondere von 1 : 99 bis 50 : 50 sein. B. from 1: 99 to 99: 1, preferably in front of from 1: 99 to 75: 25 and especially from 1: 99 to 50: its 50th

Die Copolymerisation kann als Masse-, Suspensions-, Emulsions- oder Lösungspolymerisation geführt werden. The copolymerization can be run as mass, suspension, emulsion or solution. Der Mechanismus der Copolymerisation ist an sich unerheblich, wenngleich die radikalische Polymerisation ggf. in Gegenwart geeigneter Starter bevorzugt wird. The mechanism of copolymerization is important in itself, although the radical polymerization is, if necessary, preferably in the presence of suitable starter.

Als Comonomere sind alle die Monomeren geeignet, die sich mit ω-(Vinyl benzoyl)-poly-(2,6-dimethyl-1,4-phenylenether) copolymerisieren lassen. Suitable comonomers are all suitable monomers which can be copolymerized with ω- (vinyl benzoyl) -poly (2,6-dimethyl-1,4-phenylene ether). Als copolymerisierbare Monomere können ethylenisch ungesättigte und/oder vinylisch ungesättigte Monomere und/oder Monomere mit einer Acrylat- und/ oder Alkylacrylateinheit verwendet werden. As monomers copolymerizable ethylenically unsaturated and / or vinylically unsaturated monomers and / or monomers having an acrylate and / or alkyl acrylate may be used.

Beispielhaft seien genannt: Examples include:
Ethylen, α-Olefine, Vinylchlorid, Styrol, alkylsubstituierte Styrole, α-Methylstyrol, Vinyl- und Isopropenylnaphthalin, (Meth-)acrylnitril, (Meth-)acrylsäure, Maleinsäure, Maleinsäureanhydrid, Vinylacetat, Ester der Acrylsäure bzw. Methacrylsäure, deren Alkoholteil 1 bis 20 C-Atome trägt. Ethylene, α-olefins, vinyl chloride, styrene, alkyl-substituted styrenes, α-methyl styrene, vinyl and isopropenyl, (meth) acrylonitrile, (meth) acrylic acid, maleic acid, maleic anhydride, vinyl acetate, esters of acrylic acid or methacrylic acid, the alcohol moiety 1 transmits to 20 carbon atoms. Die Comonomeren können selbst weitere funktionelle Gruppen (z. B. Epoxi, Ester, Amid usw.) tragen. The comonomers can carry even more functional groups (eg. As epoxy, ester, amide, etc.).

Es versteht sich, daß auch Mischungen verschiedener Comonomerer verwendet werden können. It is understood that mixtures of different comonomers may be used.

Die Polymeren können durch Fällung, Entgasen des Lösungsmittels in einem Entgasungsextruder oder einem Dünnfilmverdampfer isoliert werden. The polymers can be isolated in a devolatilizing extruder or a thin film evaporator by precipitation, devolatilization of the solvent.

Die Pfropfcopolymeren können für viele Zwecke eingesetzt werden. The graft copolymers can be used for many purposes. Anwendungsbeispiele sind Haftvermittler, Verträglichkeitsvermittler in Polymerlegierungen oder Kautschuke in Werkstoffen. Applications include adhesion promoters, compatibilizers in polymer alloys or rubbers in materials.

Herstellung von Poly-(2,6-dimethyl-1,4-phenylenether) Preparation of poly (2,6-dimethyl-1,4-phenylene ether)

Ausgehend von p-Chlor-2,6-dimethylphenol wurden nach dem in Makromol. Starting from p-chloro-2,6-dimethylphenol were prepared by the in Makromol. Chem. 186, 1838 (1985) beschriebenen Verfahren zwei unterschiedliche Produkte hergestellt. Chem. 186, 1838 (1985), two different products are manufactured. Mittels GPC wurde das Molekulargewicht bestimmt. GPC determined molecular weight.

PPE-1: M n = 3 000 PPE-1: M n = 3000
PPE-2: M n =13 400 PPE-2: M n = 13,400

Beispiel example Herstellung von ω-(4-Vinylbenzoyl)-poly-(2,6-dimethyl-1,4-phenylenether) (VB-PPE) Preparation of ω- (4-vinylbenzoyl) -poly (2,6-dimethyl-1,4-phenylene ether) (PPE-VB)

VB-PPE-1 bzw. VB-PPE-2 VB-PPE-1 and PPE-2-VB
30 g PPE-1 bzw. PPE-2 werden unter Stickstoff in jeweils 350 g Pyridin gelöst. 30 g of PPE-1 and PPE-2 is dissolved under nitrogen in each 350 g of pyridine. Bei 0°C wird ein 10molarer Überschuß an 4-Vinylbenzoylchlorid unter Rühren zugegeben. At 0 ° C a 10 molar excess of 4-vinyl benzoyl chloride is added under stirring. Nach 24 h wird das jeweilige Produkt durch Fällung aus Methanol isoliert. After 24 h, the respective product is isolated by precipitation from methanol.

Vergleichsversuch: VP-PPE Comparison Test: VP-PPE

Die polymerisierbare Endgruppe wird über eine Etherbindung anstelle der erfindungsgemäßen Esterbindung eingeführt. The polymerizable end group is introduced via an ether linkage instead of the inventive Esterbindung.

25 g PPE-2 wurden unter Stickstoff in 250 ml Toluol gelöst. 25 g of PPE-2 were dissolved under nitrogen in 250 ml toluene. Bei Raumtemperatur wird ein 10molarer Überschuß an 4-Vinylbenzylchlorid, 10,6 g 3n NaOH und 1,08 g Tetrabutylammoniumhydrogensulfat als Phasentransferkatalysator unter Rühren zugegeben. At room temperature, a 10 molar excess of 4-vinylbenzyl chloride, 10.6 g NaOH and 1.08 g of tetrabutylammonium hydrogen sulfate 3n is added as a phase transfer catalyst, with stirring. Nach 24 h wird das Produkt durch Fällung aus Methanol isoliert. After 24 h the product is isolated by precipitation from methanol.

Der Nachweis der vollständigen Umsetzung erfolgte jeweils mittels 1 H-NMR- Spektroskopie, GPC und UV-Spektroskopie (vgl. Makromol. Chem. 88, 215 (1965) und J. Polym. Sci., Part A, Polym. Chem. 25, 2605 (1987)). The detection of the complete reaction was carried out in each case by means of 1 H-NMR spectroscopy, GPC and UV spectroscopy (see FIG. Makromol. Chem. 88, 215 (1965) and J. Polym. Sci., Part A, Polym. Chem. 25, 2605 (1987)).

In allen drei Fällen war die Umsetzung quantitativ. In all three cases, the reaction was quantitative.

Copolymerisation des VB-PPE-2 mit Ethylacrylat 3 g VB-PPE-2 und 7 g Ethylacrylat werden in 50 g Toluol unter Stickstoff gelöst. Copolymerization of VB-2 PPE-g with ethyl 3-VB PPE-2 and 7 g of ethyl acrylate are dissolved in 50 g of toluene under nitrogen. Nach Zusatz von 0,03 g AIBN als Starter wurde 30 h bei 60°C poly merisiert. After addition of 0.03 g AIBN as initiator h at 60 ° C poly merized 30th

Das entstandene Polymere wurde in einer Mischung aus 4 Vol.-Teilen Petrol ether und 1 Vol.-Teil Methanol gefällt und getrocknet. The resulting polymer was ether in a mixture of 4 parts by volume of petrol and precipitated 1 part by volume of methanol and dried. Ausbeute: 88%. Yield: 88%.

Der Vergleichsversuch wurde wie vorstehend beschrieben, jedoch durch Copolymerisation des VB-PPE* mit Ethylacrylat angestellt. The comparative experiment was performed as described above, but made by copolymerization of VB-PPE * with ethyl acrylate.

Die Ausbeute beim Vergleichsprodukt war 85%. The yield when comparing product was 85%.

Beide Proben wurden mittels GPC und DSC untersucht: Beide Proben weisen in der DSC zwei Glasstufen auf: -11°C und 206°C. Both samples were analyzed by GPC and DSC: Both samples have as a DSC two glass stages: -11 ° C and 206 ° C. Unterschiede ergeben sich dagegen im GPC-Diagramm: während in der erfindungsgemäßen Probe im Endprodukt kein VB-PPE-2 mehr enthalten ist erkennt man in der Vergleichsprobe ein deutliches Signal von nicht umgesetztem VB-PPE*. Differences arise, however in the GPC chart: while in the inventive sample in the final product no VB PPE-2 is more seen in the comparison sample a clear signal of unreacted VB PPE *.

Claims (4)

  1. 1. Makromonomere der allgemeinen Formel I in der R 1 und R 2 Niederalkyl und R 3 Wasserstoff oder Niederalkyl und n einen Polymerisationsgrad von mindestens 5 bedeutet. 1. macromonomers of the general formula I in which R 1 and R 2 is lower alkyl and R 3 is hydrogen or lower alkyl and n is a degree of polymerization of at least. 5
  2. 2. Makromonomere der allgemeinen Formel Ia mit n=5 bis 200. 2. macromonomers of the general formula Ia with n = 5 to 200 microns.
  3. 3. ω-(4-Vinyl-)benzoyl-poly-(2,6-dimethyl-1,4-phenylenether) mit einem Polymerisationsgrad n des Phenylenethers von 5 bis 200. 3. ω- (4-vinyl) benzoyl-poly (2,6-dimethyl-1,4-phenylene ether) having a polymerization degree n of the phenylene ether of 5 to 200.
  4. 4. Verwendung der Makromonomeren nach Anspruch 1 zur Herstellung von Copolymeren. 4. Use of the macromonomers according to claim 1 for the preparation of copolymers.
DE19914103140 1991-02-02 1991-02-02 Macro-monomer(s) for prepn. of graft copolymers - partic. omega-(vinyl:benzoyl)-poly-(2,6-di:methyl)-1,4-phenylene] ethers] Withdrawn DE4103140A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19914103140 DE4103140A1 (en) 1991-02-02 1991-02-02 Macro-monomer(s) for prepn. of graft copolymers - partic. omega-(vinyl:benzoyl)-poly-(2,6-di:methyl)-1,4-phenylene] ethers]

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19914103140 DE4103140A1 (en) 1991-02-02 1991-02-02 Macro-monomer(s) for prepn. of graft copolymers - partic. omega-(vinyl:benzoyl)-poly-(2,6-di:methyl)-1,4-phenylene] ethers]

Publications (1)

Publication Number Publication Date
DE4103140A1 true true DE4103140A1 (en) 1992-08-13

Family

ID=6424232

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19914103140 Withdrawn DE4103140A1 (en) 1991-02-02 1991-02-02 Macro-monomer(s) for prepn. of graft copolymers - partic. omega-(vinyl:benzoyl)-poly-(2,6-di:methyl)-1,4-phenylene] ethers]

Country Status (1)

Country Link
DE (1) DE4103140A1 (en)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002004547A1 (en) * 2000-07-10 2002-01-17 General Electric Company Composition and process for the manufacture of functionalized polyphenylene ether resins
US6521703B2 (en) 2000-01-18 2003-02-18 General Electric Company Curable resin composition, method for the preparation thereof, and articles derived thereform
US6593391B2 (en) 2001-03-27 2003-07-15 General Electric Company Abrasive-filled thermoset composition and its preparation, and abrasive-filled articles and their preparation
US6617398B2 (en) 1999-12-01 2003-09-09 General Electric Company Poly (phenylene ether)—polyvinyl thermosetting resin
US6627704B2 (en) 1999-12-01 2003-09-30 General Electric Company Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom
US6812276B2 (en) 1999-12-01 2004-11-02 General Electric Company Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom
US6878781B2 (en) 2001-03-27 2005-04-12 General Electric Poly(arylene ether)-containing thermoset composition in powder form, method for the preparation thereof, and articles derived therefrom
US6878782B2 (en) 1999-12-01 2005-04-12 General Electric Thermoset composition, method, and article
US6897282B2 (en) 2000-07-10 2005-05-24 General Electric Compositions comprising functionalized polyphenylene ether resins
US6905637B2 (en) 2001-01-18 2005-06-14 General Electric Company Electrically conductive thermoset composition, method for the preparation thereof, and articles derived therefrom
US7067595B2 (en) 2003-10-03 2006-06-27 General Electric Company Poly (arylene ether) composition and method
US7101923B2 (en) 2003-10-03 2006-09-05 General Electric Company Flame-retardant thermoset composition, method, and article
US7148296B2 (en) 2003-10-03 2006-12-12 General Electric Company Capped poly(arylene ether) composition and process
US7199213B2 (en) 2003-08-07 2007-04-03 General Electric Company Thermoset composition, method for the preparation thereof, and articles prepared therefrom
US7205035B2 (en) 2002-04-09 2007-04-17 General Electric Company Thermoset composition, method, and article
US7211639B2 (en) 2003-10-03 2007-05-01 General Electric Company Composition comprising functionalized poly(arylene ether) and ethylene-alkyl (meth)acrylate copolymer, method for the preparation thereof, and articles prepared therefrom
US7250477B2 (en) 2002-12-20 2007-07-31 General Electric Company Thermoset composite composition, method, and article
US7329708B2 (en) 2004-08-18 2008-02-12 General Electric Company Functionalized poly(arylene ether) composition and method
US8192649B2 (en) 1999-12-01 2012-06-05 Sabic Innovative Plastics Ip B.V. Capped poly(arylene ether) composition and method

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6878782B2 (en) 1999-12-01 2005-04-12 General Electric Thermoset composition, method, and article
US6812276B2 (en) 1999-12-01 2004-11-02 General Electric Company Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom
US8192649B2 (en) 1999-12-01 2012-06-05 Sabic Innovative Plastics Ip B.V. Capped poly(arylene ether) composition and method
US6617398B2 (en) 1999-12-01 2003-09-09 General Electric Company Poly (phenylene ether)—polyvinyl thermosetting resin
US6627704B2 (en) 1999-12-01 2003-09-30 General Electric Company Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom
US6521703B2 (en) 2000-01-18 2003-02-18 General Electric Company Curable resin composition, method for the preparation thereof, and articles derived thereform
US6469124B2 (en) 2000-07-10 2002-10-22 General Electric Company Functionalized polyphenylene ether resins and curable compositions comprising them
US6627708B2 (en) 2000-07-10 2003-09-30 General Electric Company Compositions comprising functionalized polyphenylene ether resins
US6780959B2 (en) 2000-07-10 2004-08-24 General Electric Company Compositions comprising functionalized polyphenylene ether resins
US6897282B2 (en) 2000-07-10 2005-05-24 General Electric Compositions comprising functionalized polyphenylene ether resins
WO2002004547A1 (en) * 2000-07-10 2002-01-17 General Electric Company Composition and process for the manufacture of functionalized polyphenylene ether resins
US6905637B2 (en) 2001-01-18 2005-06-14 General Electric Company Electrically conductive thermoset composition, method for the preparation thereof, and articles derived therefrom
US6593391B2 (en) 2001-03-27 2003-07-15 General Electric Company Abrasive-filled thermoset composition and its preparation, and abrasive-filled articles and their preparation
US6878781B2 (en) 2001-03-27 2005-04-12 General Electric Poly(arylene ether)-containing thermoset composition in powder form, method for the preparation thereof, and articles derived therefrom
US7205035B2 (en) 2002-04-09 2007-04-17 General Electric Company Thermoset composition, method, and article
US7250477B2 (en) 2002-12-20 2007-07-31 General Electric Company Thermoset composite composition, method, and article
US7226980B2 (en) 2003-08-07 2007-06-05 General Electric Company Thermoset composition, method for the preparation thereof, and articles prepared therefrom
US7199213B2 (en) 2003-08-07 2007-04-03 General Electric Company Thermoset composition, method for the preparation thereof, and articles prepared therefrom
US7211639B2 (en) 2003-10-03 2007-05-01 General Electric Company Composition comprising functionalized poly(arylene ether) and ethylene-alkyl (meth)acrylate copolymer, method for the preparation thereof, and articles prepared therefrom
US7148296B2 (en) 2003-10-03 2006-12-12 General Electric Company Capped poly(arylene ether) composition and process
US7119136B2 (en) 2003-10-03 2006-10-10 General Electric Company Flame-retardant thermoset composition, method, and article
US7101923B2 (en) 2003-10-03 2006-09-05 General Electric Company Flame-retardant thermoset composition, method, and article
US8163847B2 (en) 2003-10-03 2012-04-24 Sabic Innovative Plastics Ip B.V. Capped poly(arylene ether) composition and process
US7655734B2 (en) 2003-10-03 2010-02-02 Sabic Innovative Plastics Ip B.V. Capped poly(arylene ether) composition and process
US7067595B2 (en) 2003-10-03 2006-06-27 General Electric Company Poly (arylene ether) composition and method
US7781537B2 (en) 2004-08-18 2010-08-24 Sabic Innovative Plastics Ip B.V. Functionalized poly(arylene ether) composition and method
US7329708B2 (en) 2004-08-18 2008-02-12 General Electric Company Functionalized poly(arylene ether) composition and method

Similar Documents

Publication Publication Date Title
US3944631A (en) Acrylate-styrene-acrylonitrile composition and method of making the same
US4816520A (en) Terminally functionalized polymers and preparation thereof
Malmström et al. Development of a new class of rate-accelerating additives for nitroxide-mediated ‘living’free radical polymerization
Durmaz et al. Preparation of ABC miktoarm star terpolymer containing poly (ethylene glycol), polystyrene, and poly (tert‐butylacrylate) arms by combining diels–alder reaction, atom transfer radical, and stable free radical polymerization routes
US5237024A (en) Preparing monoalkenyl aromatic monomer-maleic half ester copolymer
US6090902A (en) Organopolysiloxane-modified graft copolymers
US5310820A (en) Process for modification of polyphenylene ether or related polymers with a cyclic acid anhydride and the use thereof in modified, high temperature rigid polymer of vinyl substituted aromatics
US4698394A (en) Reactive styrene polymers
Hückstädt et al. Synthesis of a polystyrene‐arm‐polybutadiene‐arm‐poly (methyl methacrylate) triarm star copolymer
US6380304B1 (en) Mass polymerized rubber-modified monovinylidene aromatic copolymer compositions
Ohno et al. Nitroxide‐controlled free radical polymerization of a sugar‐carrying acryloyl monomer
Jankova et al. Synthesis of amphiphilic PS-b-PEG-b-PS by atom transfer radical polymerization
US3763277A (en) Process for the preparation of inter-polymers of poly(ethylene oxide)
Dag et al. Heterograft copolymers via double click reactions using one‐pot technique
US4918159A (en) Styrene-based/polymercaptan polymer and process for production thereof
Bohnert et al. Liquid‐Crystalline side‐chain AB block copolymers by direct anionic polymerization of a mesogenic methacrylate
Jayakumar et al. Studies on copolymers of 2-(N-phthalimido) ethyl methacrylate with methyl methacrylate
Park et al. Synthesis of fluorine-containing graft copolymers of poly (perfluoroalkylethyl methacrylate)-g-poly (methyl methacrylate) by the macromonomer technique and emulsion copolymerization method
US6262179B1 (en) Process for the manufacture of a composition comprising a vinylaromatic polymer and a rubber by polymerization in the presence of a stable free radical
US4351924A (en) ω-, and α,ω-Hydroxyhydrocarbyl-(alkyl methacrylate) polymers and process
Meijs et al. Reactivity of macromonomers in free radical polymerization
US4486572A (en) Synthesis of amphiphilic block copolymers and networks
Ishizone et al. Anionic polymerizations of perfluoroalkyl methacrylates and synthesis of well-defined ABC triblock copolymers of methacrylates containing hydrophilic, hydrophobic, and perfluoroalkyl groups
US4522983A (en) Polymeric molding composition
US3487127A (en) Rubber-modified resinous polymers prepared in the presence of a polyphenylene oxide

Legal Events

Date Code Title Description
8130 Withdrawal