WO2021094858A1 - Composition de polymère à haute température compatible - Google Patents

Composition de polymère à haute température compatible Download PDF

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WO2021094858A1
WO2021094858A1 PCT/IB2020/059986 IB2020059986W WO2021094858A1 WO 2021094858 A1 WO2021094858 A1 WO 2021094858A1 IB 2020059986 W IB2020059986 W IB 2020059986W WO 2021094858 A1 WO2021094858 A1 WO 2021094858A1
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composition
compatibilized
polyarylene sulfide
iso
determined according
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PCT/IB2020/059986
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Shahram SHAFAEI
Sepehr Harsiny
Hariharan Ramalingam
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Shpp Global Technologies B.V.
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Priority to JP2022526406A priority Critical patent/JP2023501996A/ja
Priority to CN202080077905.2A priority patent/CN114729151A/zh
Publication of WO2021094858A1 publication Critical patent/WO2021094858A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/04—Epoxynovolacs
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
    • C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/02—Polythioethers; Polythioether-ethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/04—Polysulfides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C09D163/04—Epoxynovolacs
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
    • C09D181/04—Polysulfides

Definitions

  • This disclosure is directed to compatibilized epoxy compositions and methods of forming the compatibilized epoxy compositions.
  • thermoplastic blends containing semi crystalline and amorphous materials that exhibit chemical resistance and good mechanical property retention at high temperature.
  • Many semi-crystalline polymer blends demonstrate excellent chemical resistance.
  • the addition of amorphous materials to obtain high temperature property retention is not as well documented, as such polymer blends tend to be incompatible and difficult to compound without the addition of fillers or additives such as glass, talc, or mica.
  • a compatible unfilled resin blend it is often necessary to add a small amount of another ingredient or compatibilizer to promote more thorough blending between the two polymers.
  • the additional ingredient(s) can promote bond formation between the different materials. It can be difficult to identify suitable compatibilizers, as effective compatibilizers in one polymer blend may not be effective in others; a great deal depends upon the chemistry and specific functionalities of the molecules being blended and their interaction.
  • Polyetherimide is an amorphous polyimide having versatility for use in various manufacturing processes, proving amenable to techniques including injection molding, extrusion, and thermoforming, to prepare various articles.
  • Polyetherimides have high strength, toughness, heat resistance, and modulus.
  • Polyarylene sulfides such as polyphenylene sulfide are semi-crystalline thermoplastics having good mechanical properties, chemical resistance, and flame resistance.
  • compositions incorporating these two polymers In order to benefit from the individual properties of polyetherimide and polyphenylene sulfide, attempts have been made to prepare compositions incorporating these two polymers. However, combining these amorphous and semi-crystalline polymers results in domain-separated immiscible mixtures. Accordingly, there remains a continuing need for compatibilized compositions including a polyimide such as polyetherimide and a polyarylene sulfide such as polyphenylene sulfide. BRIEF DESCRIPTION
  • a compatibilized composition comprising a polyimide; and a compatibilized polyarylene sulfide composition comprising a melt blended combination of an epoxy novolac resin and a polyarylene sulfide, wherein the compatibilized composition does not comprise a polyphenylene sulfone (also known as PPSU).
  • PPSU polyphenylene sulfone
  • Also provided is a method of manufacturing the compatibilized composition including melt-mixing the epoxy novolac resin and the polyarylene sulfide to form the compatibilized polyarylene sulfide composition; and melt-mixing the compatibilized polyarylene sulfide composition and the polyimide to form the compatibilized composition, preferably wherein the melt-mixing to form the compatibilized composition is at a temperature of 250 to 360°C.
  • FIG. 1 is a scanning electron microscope (SEM) image of a comparative composition of polyetherimide (PEI) and polyphenylene sulfide (PPS) without a compatibilizer.
  • SEM scanning electron microscope
  • FIG. 2 is an SEM image of the comparative composition of Comparative Example 5, where the composition of PEI, PPS, and an epoxy cresol novolac (ECN) stabilizer was prepared by the one-step process.
  • ECN epoxy cresol novolac
  • FIG. 3 is an SEM image of Comparative Example 8, where the composition of PEI-ECN and PPS was prepared by the two-step process.
  • compatibilized compositions comprising a polyimide, such as polyetherimide or poly(sulfone etherimide), and a polyarylene sulfide, such as polyphenylene sulfide, can be prepared when the polyarylene sulfide is first melt blended with an epoxy novolac resin to act as a compatibilizer for the polyimide and the polyarylene sulfide.
  • the compatibilized compositions can achieve increased heat deflection temperature, tensile modulus, and elongation at break, and improved melt volume flow rate.
  • an aspect of the present disclosure is a compatibilized composition including a polyimide and a compatibilized polyarylene sulfide composition comprising a melt blended combination of an epoxy novolac resin and a polyarylene sulfide.
  • the compatibilized polyarylene sulfide composition is separately prepared by melt blending a composition including the polyarylene sulfide and the epoxy novolac resin. The resulting compatibilized polyarylene sulfide composition can then be combined with the polyimide to provide the compatibilized composition.
  • Polyimides comprise more than 1, for example 5 to 1000, or 5 to 500, or 10 to 100, structural units of formula (1) wherein each V is the same or different, and is a substituted or unsubstituted tetravalent C4-40 hydrocarbon group, for example a substituted or unsubstituted C6-20 aromatic hydrocarbon group, a substituted or unsubstituted, straight or branched chain, saturated or unsaturated C2-20 aliphatic group, or a substituted or unsubstituted C4-8 cycloaliphatic group, in particular a substituted or unsubstituted C6-20 aromatic hydrocarbon group.
  • each V is the same or different, and is a substituted or unsubstituted tetravalent C4-40 hydrocarbon group, for example a substituted or unsubstituted C6-20 aromatic hydrocarbon group, a substituted or unsubstituted, straight or branched chain, saturated or unsaturated C2-20 aliphatic group, or a substitute
  • Each R in formula (1) is the same or different, and is a substituted or unsubstituted divalent organic group, such as a C6-20 aromatic hydrocarbon group or a halogenated derivative thereof, a straight or branched chain C 2-20 alkylene group or a halogenated derivative thereof, a C 3-8 cycloalkylene group or halogenated derivative thereof, in particular a divalent group of formulas (2) aryl, - C y th y - wherein y is an integer from 1 to 5 or a halogenated derivative thereof (which includes perfluoroalkylene groups), or -(CeHmj z - wherein z is an integer from 1 to 4.
  • R is m- phenylene, p-phenylene, or a diaryl sulfone.
  • Polyetherimides are a class of polyimides that comprise more than 1, for example 10 to 1000, or 10 to 500, structural units of formula (3) wherein each R is the same or different, and is as described in formula (1).
  • the polyetherimide can be a poly(sulfone etherimide).
  • at least some groups R in Formula (3) are a sulfone group (-SO2-) .
  • T is -O- or a group of the formula -O-Z-O- wherein the divalent bonds of the -O- or the -O-Z-O- group are in the 3,3', 3,4', 4,3', or the 4,4' positions.
  • the group Z in -O-Z-O- of formula (3) is a substituted or unsubstituted divalent organic group, and can be an aromatic C6-24 monocyclic or polycyclic moiety optionally substituted with 1 to 6 Ci-s alkyl groups, 1 to 8 halogen atoms, or a combination thereof, provided that the valence of Z is not exceeded.
  • Exemplary groups Z include groups derived from a dihydroxy compound of formula (4) wherein R a and R b can be the same or different and are a halogen atom or a monovalent Ci- 6 alkyl group, for example; p and q are each independently integers of 0 to 4; c is 0 to 4; and X a is a bridging group connecting the hydroxy-substituted aromatic groups, where the bridging group and the hydroxy substituent of each Ce arylene group are disposed ortho, meta, or para (specifically para) to each other on the Ce arylene group.
  • the bridging group X a can be a single bond, -0-, -S-, -S(O)-, -S(0) 2 -, -C(O)-, or a Ci-is organic bridging group.
  • the C MS organic bridging group can be cyclic or acyclic, aromatic or non-aromatic, and can further comprise heteroatoms such as halogens, oxygen, nitrogen, sulfur, silicon, or phosphorous.
  • the Ci-is organic group can be disposed such that the Ce arylene groups connected thereto are each connected to a common alkylidene carbon or to different carbons of the Ci-is organic bridging group.
  • a specific example of a group Z is a divalent group of formula (4a) wherein Q is -0-, -S-, -C(O)-, -SO2-, -SO-, or -C y th y - wherein y is an integer from 1 to 5 or a halogenated derivative thereof (including a perfluoroalkylene group).
  • Z is a derived from bisphenol A, such that Q in formula (3a) is 2,2-isopropylidene.
  • R is m-phenylene or p-phenylene and T is -O-Z-O- wherein Z is a divalent group of formula (4a).
  • R is m-phenylene or p-phenylene and T is -O-Z-O wherein Z is a divalent group of formula (4a) and Q is 2,2-isopropylidene.
  • additional structural imide units preferably comprise less than 20 mole percent (mol%) of the total number of units, and more preferably can be present in amounts of 0 to 10 mol% of the total number of units, or 0 to 5 mol% of the total number of units, or 0 to 2 mol% of the total number of units. In some aspects, no additional imide units are present in the polyetherimide.
  • Copolymers of the polyetherimides can be manufactured using a combination of an aromatic bis(ether anhydride) of formula (5) and a different bis(anhydride), for example a bis(anhydride) wherein T does not contain an ether functionality, for example T is a sulfone.
  • bis(anhydride)s include 3,3-bis[4-(3,4- dicarboxyphenoxy)phenyl]propane dianhydride; 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl ether dianhydride; 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfide dianhydride; 4,4'-bis(3,4- dicarboxyphenoxy)benzophenone dianhydride; 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride; 2,2-bis[4-(2,3-dicarboxyphenoxy)phenyl]propane dianhydride; 4,4'-bis(2,3- dicarboxyphenoxy)diphenyl ether dianhydride; 4,4'-bis(2,3-dicarboxyphenoxy)diphenyl sulfide dianhydride; 4,4'-bis(2,3-dicarboxyphenoxy)diphen
  • organic diamines include hexamethylenediamine, polymethylated 1,6-n-hexanediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, 1,12-dodecanediamine, 1,18-octadecanediamine, 3- methylheptamethylenediamine, 4,4-dimethylheptamethylenediamine, 4- methylnonamethylenediamine, 5-methylnonamethylenediamine, 2,5- dimethylhexamethylenediamine, 2,5-dimethylheptamethylenediamine, 2, 2- dimethylpropylenediamine, N-methyl-bis (3-aminopropyl) amine, 3- methoxyhexamethylenediamine, l,2-bis(3-aminopropoxy) ethane, bis(3-aminopropyl) sulfide, 1,4-cyclohexanediamine, bis-(4-a
  • any regioisomer of the foregoing compounds can be used. Combinations of these compounds can also be used.
  • the organic diamine is m-phenylenediamine, p- phenylenediamine, 4,4'-diaminodiphenyl sulfone, or a combination thereof.
  • the poly(etherimide) can also be a copolymer comprising polyetherimide units of formula (1) and siloxane blocks of formula (7) wherein E has an average value of 2 to 100, 2 to 31, 5 to 75, 5 to 60, 5 to 15, or 15 to 40, each R’ is independently a Cm monovalent hydrocarbyl group.
  • each R’ can independently be a Ci-13 alkyl group, Ci-13 alkoxy group, C2-13 alkenyl group, C2-13 alkenyloxy group, C3-6 cycloalkyl group, C3-6 cycloalkoxy group, C6-14 aryl group, C6-10 aryloxy group, C7-13 arylalkyl group, C7-13 arylalkoxy group, C7-13 alkylaryl group, or C7-13 alkylaryloxy group.
  • the foregoing groups can be fully or partially halogenated with fluorine, chlorine, bromine, or iodine, or a combination thereof. In an aspect, no bromine or chlorine is present, and in another aspect, no halogens are present.
  • the polysiloxane blocks comprises R’ groups that have minimal hydrocarbon content.
  • an R’ group with a minimal hydrocarbon content is a methyl group.
  • the poly (siloxane-etherimide)s can be formed by polymerization of an aromatic bis(ether anhydride) of formula (5) and a diamine component comprising an organic diamine (6) as described above or a combination of diamines, and a polysiloxane diamine of formula (8) wherein R’ and E are as described in formula (9), and R 4 is each independently a C2-C20 hydrocarbon, in particular a C2-C20 arylene, alkylene, or arylenealkylene group.
  • R 4 is a C2-C20 alkylene group, specifically a C2-C10 alkylene group such as propylene, and E has an average value of 5 to 100, 5 to 75, 5 to 60, 5 to 15, or 15 to 40.
  • Procedures for making the polysiloxane diamines of formula (10) are well known in the art.
  • the diamine component can contain 10 to 90 mole percent (mol %), or 20 to 50 mol%, or 25 to 40 mol% of polysiloxane diamine (8) and 10 to 90 mol%, or 50 to 80 mol%, or 60 to 75 mol% of diamine (6), for example as described in US Patent 4,404,350.
  • the diamine components can be physically mixed prior to reaction with the bisanhydride(s), thus forming a substantially random copolymer.
  • block or alternating copolymers can be formed by selective reaction of (6) and (8) with aromatic bis(ether anhydrides (5), to make polyimide blocks that are subsequently reacted together.
  • the poly(siloxane-imide) copolymer can be a block, random, or graft copolymer.
  • the copolymer is a block copolymer.
  • poly(siloxane-etherimide)s examples include US Pat. Nos. 4,404,350, 4,808,686 and 4,690,997.
  • the poly(siloxane-etherimide) has units of formula (9) wherein R’ and E of the siloxane are as in formula (7), R and Z of the imide are as in formula (1), R 4 is as in formula (8), and n is an integer from 5 to 100.
  • R of the etherimide is a phenylene
  • Z is a residue of bisphenol A
  • R 4 is n-propylene
  • E is 2 to 50, 5, to 30, or 10 to 40
  • n is 5 to 100
  • each R’ of the siloxane is methyl.
  • the relative amount of polysiloxane units and etherimide units in the poly(siloxane-etherimide) depends on the desired properties, and are selected using the guidelines provided herein.
  • the block or graft poly(siloxane- etherimide) copolymer is selected to have a certain average value of E, and is selected and used in amount effective to provide the desired weight percent (wt%) of polysiloxane units in the composition.
  • the poly(siloxane-etherimide) comprises 10 to 50 wt%, 10 to 40 wt%, or 20 to 35 wt% polysiloxane units, based on the total weight of the poly(siloxane-etherimide).
  • the polyimides and polyetherimides can have a melt index of 0.1 to 10 grams per minute (g/min), as measured by American Society for Testing Materials (ASTM) D1238 at 340 to 370°C, using a 6.7 kilogram (kg) weight.
  • the polyetherimide polymer has a weight average molecular weight (Mw) of 1,000 to 150,000 grams/mole (g/mol), as measured by gel permeation chromatography, using polystyrene standards.
  • the polyetherimide has an Mw of 10,000 to 80,000 g/mol.
  • Such polyetherimide polymers typically have an intrinsic viscosity greater than 0.2 deciliters per gram (dl/g), or, more specifically, 0.35 to 0.7 dl/g as measured in m-cresol at 25°C.
  • the compatibilized composition further includes the compatibilized polyarylene sulfide composition.
  • the compatibilized polyarylene sulfide composition includes a separately melt blended combination or composition including an epoxy novolac resin and a polyarylene sulfide.
  • the polyarylene sulfide (referred to hereinafter as "PPS") are derived from the known polymers containing arylene groups separated by sulfur atoms.
  • the preferred poly(arylene sulfide) resins include various poly(phenylene sulfide)s, for example, poly(p- phenylene sulfide) and substituted poly(phenylene sulfide)s.
  • PPS polymers includes at least 70 mole % (mol%), preferably at least 90 mol% of repeating structural units of formula (10) wherein each occurrence of Z 1 independently comprises halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; and each occurrence of Z 2 independently comprises hydrogen, halogen, unsubstituted or substituted C1-C12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C1-C12 hydrocarbylthio, C1-C12 hydrocarbyloxy, or C2-C12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen
  • the PPS can be a linear or branched homopolymer or copolymer.
  • Linear PPS containing at least 70 mol% of a repeating unit of the formula (7) has a high degree of crystallinity, with excellent thermal resistance, chemical resistance, and mechanical strength.
  • the PPS can be prepared using methods that are known in the art.
  • a process for producing poly ary lene sulfide can include reacting a material that provides a hydrosulfide ion, e.g., an alkali metal sulfide, with a dihalobenzene in an organic amide solvent.
  • PPS is commercially available, for example, a FORTRON polyphenylene sulfide available from Celanese.
  • the alkali metal sulfide can be, for example, lithium sulfide, sodium sulfide, potassium sulfide, rubidium sulfide, cesium sulfide or a mixture thereof.
  • the alkali metal sulfide is a hydrate or an aqueous mixture
  • the alkali metal sulfide can be processed according to a dehydrating operation in advance of the polymerization reaction.
  • An alkali metal sulfide can also be generated in situ.
  • an alkali metal hydroxide can be included in the reaction to remove or react impurities such as an alkali metal polysulfide or an alkali metal thiosulfate.
  • the dihaloaromatic compound can be, without limitation, an o-dihalobenzene, m- dihalobenzene, p-dihalobenzene, methoxy-dihalobenzene, dihalobenzoic acid, or dihalotoluene, where the halogen atom can be fluorine, chlorine, bromine, or iodine, and 2 halogen atoms in the same dihalo-aromatic compound may be the same or different from each other.
  • Corresponding dihaloaromatic compounds to prepare polyarylene sulfides can include dihalobiphenyl, dihalodiphenyl ether, dihalodiphenyl sulfone, dihalodiphenyl sulfoxide, or dihalodiphenyl ketone, where the halogen atom can be fluorine, chlorine, bromine, or iodine, and 2 halogen atoms in the same dihalo-aromatic compound may be the same or different from each other.
  • dihaloaromatic compounds include 1,4-dichloronaphthalene, 4,4'-dichlorobiphenyl, 4,4'-dichlorodiphenyl ether, 4,4'-dichlorodiphenylsulfone, 4,4'- dichlorodiphenylsulfoxide, and 4,4'-dichlorodiphenyl ketone.
  • the process for manufacturing PPS can include carrying out the polymerization reaction in an organic amide solvent.
  • organic amide solvents include, without limitation, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N,N-dimethylformamide, N,N- dimethylacetamide, N-methylcaprolactam, tetramethylurea, dimethylimidazolidinone, hexamethyl phosphoric acid triamide, and mixtures thereof.
  • the amount of the organic amide solvent used in the reaction can be, e.g., from 0.2 to 5 kilograms per mole (kg/mol) of the effective amount of the alkali metal sulfide.
  • the polymerization can be carried out by a step-wise polymerization process.
  • the first polymerization step can include introducing the dihaloaromatic compound to a reactor, subjecting the dihaloaromatic compound to a polymerization reaction in the presence of water at a temperature of from 180 to 235°C, and continuing polymerization until the conversion rate of the dihaloaromatic compound attains to not less than about 50 mol% of the theoretically necessary amount.
  • the PPS product can also be treated to remove unwanted contaminating ions by immersing the resin in deionized water or by treatment with an acid, typically hydrochloric acid, sulfuric acid, phosphoric acid, or acetic acid.
  • an acid typically hydrochloric acid, sulfuric acid, phosphoric acid, or acetic acid.
  • the impurity level can be represented as the percent by weight ash remaining after burning a PPS sample.
  • the ash content of the PPS is preferably less than 1% by weight, more preferably less than 0.5% by weight, even more preferably less than 0.1% by weight.
  • melt viscosity of PPS is not particularly limited, a melt viscosity of at least 100 Poise is preferred from the viewpoint of the toughness and 10,000 Poise or less is preferred from the viewpoint of the injection moldability.
  • the PPS can have an M w from 5,000 to 100,000 g/mol, as determined by gel permeation chromatography (GPC) using polystyrene standards according to ASTM D5296.
  • the melt blended combination of the compatibilized polyarylene sulfide composition further includes an epoxy novolac resin in an amount effective to compatibilize the polyarylene sulfide and the polyimide.
  • the epoxy novolac resin can have an average epoxy equivalent of at least 2 units per molecule, or an average of greater than or equal to 6 pendant epoxy groups per molecule, or, more specifically, an average of greater than or equal to 20 pendant epoxy groups per molecule or, more specifically, an average of greater than or equal to 50 pendant epoxy groups per molecule.
  • the epoxy novolac resin can have 2 to 8 pendant epoxy groups per molecule, or 3 to 7 pendant epoxy groups per molecule, or 4 to 6 pendant epoxy groups per molecule.
  • the epoxy novolac resin can interact with the polyarylene sulfide. This interaction can be chemical (e.g. grafting) or physical (e.g. affecting the surface characteristics of the disperse phases). When the interaction is chemical, the epoxy groups of the epoxy novolac resin can be partially or completely reacted with the polyarylene sulfide such that the melt blended combination of the polyarylene sulfide and the epoxy novolac resin can comprise a reaction product.
  • the epoxy novolac resin can be made by reacting a phenol with formaldehyde.
  • phenol as used herein includes substituted and unsubstituted phenyl, aryl, and fused aromatic rings having a hydroxyl group.
  • the molar ratio of formaldehyde to phenol is less than 1.
  • the novolac resin can be functionalized with epoxy groups by reacting the novolac resin with epichlorohydrin in the presence of sodium hydroxide as a catalyst.
  • the epoxy novolac resin can have an M w of 500 to 2,500 g/mol, preferably 540 to 2,000 g/mol as determined by GPC. Also, within this range the epoxy novolac resin can have a M w of less than or equal to 900 g/mol, as determined by GPC.
  • the epoxy novolac resin can have an epoxy equivalent of 0.3 to 0.8, preferably 0.35 to 0.6, more preferably 0.425 to 0.5 per 100 g of the epoxy novolac resin.
  • the epoxy novolac resin can have a weight per epoxide, or epoxide equivalent weight (EEW) of 100 to 500, preferably 150 to 350, more preferably 200 to 250, even more preferably 200 to 235.
  • the epoxy novolac resin can be an epoxy phenol novolac (EPN) resin, an epoxy cresol novolac (ECN) resin, or a combination thereof.
  • the epoxy novolac resin can include units of formula (11) wherein m is 0 or 1.
  • the epoxy novolac resin preferably comprises an epoxy o-cresol novolac resin.
  • the epoxy novolac resin can be an ECN having an M w of 540 to 2,000 g/mol (by GPC), an epoxy equivalent of 0.425 to 0.5 per 100 g of ECN, and an EEW of 200 to 235.
  • epoxy-containing materials other than the epoxy novolac resin can be excluded from the composition.
  • the composition can exclude epoxy- functionalized styrenic polymers such as epoxy-functionalized styrene acrylate oligomers.
  • the epoxy novolac resin can be included in the melt blended combination, or in a precursor composition of the polyarylene sulfide and the epoxy novolac resin before melt blending, in an amount of 1 to 20 wt%, based on the weight of compatibilized polyarylene sulfide composition or the weight of the melt blended combination.
  • the compatibilized polyarylene sulfide composition can be prepared from the melt blended combination of 80 to 99 wt%, preferably 85 to 98 wt%, more preferably 90 to 98 wt% of the polyarylene sulfide, and 1 to 20 wt%, preferably 2 to 15 wt%, more preferably 2 to 10 wt% of the epoxy novolac resin, each based on the total weight of the compatibilized polyarylene sulfide composition.
  • the compatibilized composition can include 10 to 90 wt% of the polyimide and 10 to 90 wt% of the compatibilized polyarylene sulfide composition, preferably 20 to 80 wt% of the polyimide and 20 to 80 wt% of the compatibilized polyarylene sulfide composition, more preferably 30 to 70 wt% of the polyimide and 30 to 70 wt% of the compatibilized polyarylene sulfide composition, based on the total weight of the compatibilized composition.
  • the compatibilized composition includes 35 to 50 wt% of a polyimide and 50 to 65 wt% of the compatibilized polyarylene sulfide composition, based on the total weight of the compatibilized composition.
  • the compatibilized composition includes 30 to 55 wt% of a polyimide and 45 to 70 wt% of the compatibilized polyarylene sulfide composition, based on the total weight of the compatibilized composition.
  • reinforcing fillers examples include glass beads (hollow and/or solid), glass flake, milled glass, glass fibers, talc, wollastonite, silica, mica, kaolin or montmorillonite clay, silica, quartz, barite, and the like, and combinations comprising any of the foregoing reinforcing fillers.
  • Antioxidants can be compounds such as phosphites, phosphonites, and hindered phenols or mixtures thereof. Phosphorus containing stabilizers including triaryl phosphite and aryl phosphonates are of note as useful additives. Difunctional phosphorus containing compounds can also be employed.
  • Stabilizers can have a molecular weight greater than or equal to 300.
  • the compatibilized composition can include a particulate material.
  • exemplary particulate materials include fumed silica, fused silica, precipitated silica, silica gel, polysilsesquioxane, quartz, diatomaceous earth, milled glass, glass spheres, or a combination thereof.
  • the particulate material can have a particle size of 0.1 to 200 micrometers (mhi), for example 0.5 to 150 mhi or 1 to 100 mhi.
  • the particle size can be 0.1 to 20 mhi, for example 0.5 to 15 mhi.
  • the particle size can be 25 to 150 mhi, for example 50 to 100 mhi.
  • the compatibilized composition can include two or more different particulate materials, where the particle size of each particulate material is the same or different.
  • the compatibilized composition can include a first particulate material having a particle size of 50 to 100 mhi and a second particulate material having a particle size of 0.5 to 12 mhi.
  • the compatibilized composition does not comprise a particulate material, conductive filler, or reinforcing filler.
  • the compatibilized composition does not include a particulate material or a glass fiber.
  • the compatibilized composition can be prepared by a) melt-mixing the epoxy novolac resin and the polyarylene sulfide to form the compatibilized polyarylene sulfide composition; and b) melt-mixing the compatibilized polyarylene sulfide composition and the polyimide to form the compatibilized composition; wherein step a) and step b) are carried out sequentially.
  • steps a) and b) can be conducted at a temperature of 250 to 360°C.
  • the melt- mixing of the epoxy novolac resin and the polyarylene sulfide to form the compatibilized polyarylene sulfide composition of step a) is performed in an initial pass in an extruder, and melt-mixing of the compatibilized polyarylene sulfide composition and the polyimide to form the compatibilized composition in step b) is performed in a second pass through the extruder.
  • the method of making the compatibilized composition is further described in the working examples below.
  • the compatibilized composition can have a heat deflection temperature of greater than or equal to 180 to 220°C, preferably 185 to 210°C, as determined according to ISO-75 at a pressure of 0.45 MPa.
  • the compatibilized composition can have an impact strength of greater than or equal to 4.5 kJ/m 2 , preferably greater than or equal to 4.6 kJ/m 2 , as determined according to ISO- 180.
  • the heat deflection temperature and the tensile modulus of the compatibilized composition are greater than a heat deflection temperature and a tensile modulus of a comparable composition that does not include the compatibilized polyarylene sulfide composition.
  • the comparable composition includes the same amounts of the polyimide, the polyarylene sulfide, and the epoxy novolac resin as the compatibilized composition, but the polyarylene sulfide and the epoxy novolac resin are not melt blended as a compatibilized polyarylene sulfide composition in the comparable composition.
  • the morphology of the compatibilized composition has a domain size that is less than a domain size of a comparable composition.
  • Domain size is determined by Transmission Electron Microscopy (TEM) as follows. A sample of the composition is injection molded into a sample 60 millimeters square and having a thickness of 3.2 millimeters. A block (5 millimeters by 10 millimeters) is cut from the middle of the sample. The block is then sectioned from top to bottom by an ultra microtome using a diamond knife at room temperature. The sections are 100 nanometers thick. At least 5 sections are scanned by TEM at 100 to 120 kilovolts (kV) and the images are recorded at 66,000x magnification. The domains were counted and measured, the domain size reflecting the longest single linear dimension of each domain. The domain sizes over the 5 sections were then averaged to yield the average domain size. As used herein, “domain size” refers to the average domain size.
  • the compatibilized composition includes 10 to 90 wt%, preferably 20 to 80 wt%, more preferably 30 to 70 wt% of the polyimide and 10 to 90 wt% of the compatibilized polyarylene sulfide composition, each based on the total weight of the compatibilized composition, wherein the compatibilized polyarylene sulfide composition is prepared from the melt blended combination of: 80 to 99 wt%, preferably 85 to 98 wt%, more preferably 90 to 98 wt% of the polyarylene sulfide, and 1 to 20 wt%, preferably 2 to 15 wt%, more preferably 2 to 10 wt% of the epoxy novolac resin, each based on the total weight of the compatibilized polyarylene sulfide composition.
  • the heat deflection temperature and the tensile modulus of the compatibilized composition are greater than a heat deflection temperature and a tensile modulus of a comparable composition, wherein the comparable composition comprises a same amount of the polyimide, a same amount of the polyarylene sulfide, and a same amount of the epoxy novolac resin as the compatibilized composition, and wherein the polyarylene sulfide and the epoxy novolac resin are not melt blended as a compatibilized polyarylene sulfide composition in the comparable composition.
  • the compatibilized composition includes 30 to 55 wt% of a poly(sulfone etherimide), 45 to 70 wt% of the compatibilized polyarylene sulfide composition, and does not include a particulate material or a glass fiber, and the compatibilized composition has a melt volume flow rate of 25 to 40 cm 3 /10 min, as determined according to ISO- 1133 at 360°C/5 kg, an elongation at break of greater than or equal to 50%, as determined according to ISO-527, a heat deflection temperature of greater than 180°C, as determined according to ISO- 75 at a pressure of 0.45 MPa, and a heat deflection temperature of greater than or equal to 135°C, as determined according to ISO-75 at a pressure of 1.8 MPa.
  • the compatibilized composition can have an elongation at break of greater than or equal to 40%, preferably greater than or equal to 50%, as determined according to ISO-527.
  • the compatibilized composition is also useful for forming a variety of articles.
  • Exemplary methods of forming such articles include single layer and multilayer sheet extrusion, injection molding, blow molding, film extrusion, profile extrusion, pultrusion, compression molding, thermoforming, pressure forming, hydroforming, vacuum forming, or the like. Combinations of the foregoing article fabrication methods can be used.
  • the composition can be particularly useful for forming electronic components, for example, a composition of a consumer electronic device.
  • Polymer blends were prepared using a two-pass method in which PEI or PPS was melt mixed with ECN to produce a modified polyetherimide (PEI-E) or polyphenylene sulfide (PPS-E) masterbatch.
  • Compositions were prepared by melt mixing either 1) PEI-E and PPS, or 2) PPS-E and PEI by compounding using extrusion in a 6.4 cm twin screw, vacuum vented extruder at 20 Kg/h. Material blends evaluated are presented in the Tables below. The extruder temperature was profiled and ranged from 300 to 335°C at the feed throat. The screw speed was 300 rotations per minute (rpm) under vacuum. The extmdate was cooled, pelletized, and dried.
  • the resin was dried at 140°C for 5 hours in preparation for injection molding of test samples.
  • Polymer blends were injection molded into ISO test samples using a barrel temperature of 320 to 340°C with a mold temperature of 130 to 150°C and a 32 to 35 second cycle time.
  • An optional additive was added during melt mixing of the polymer blends.
  • Examples 1 to 8 The purpose of Examples 1 to 8 was to demonstrate the effect of PPS and ECN as compatibilizers for PEI compositions. Compositions were prepared and tested in accordance with the procedures described above. Compositions and properties for Examples 1 to 8 are shown in Table 2. Table 2
  • Example 3 is a combination of 98 wt% of PPS and 2 wt% of ECN, which is the ECN-modified polyphenylene sulfide (PPS-E) without additional polymers.
  • Example 4 is a combination of 98 wt% of PEI and 2 wt% of ECN, which is the ECN-modified polyetherimide (PEI-E) without additional polymers.
  • Table 1 shows the amount of PPS-E or PEI-E in parentheses as 100 wt%.
  • Examples 7 and 8 were prepared using the PPS-E or PEI-E as prepared for Examples 3 and 4, respectively. Accordingly, the compatibilized polyphenylene sulfide composition (PPS-E) in Example 7 is a melt blended combination of 98 wt% of PPS and 2 wt% of ECN.
  • Example 7 demonstrate that the ECN-modified polyphenylene sulfide (PPS- E) in combination with PEI (Example 7) provides a composition capable of achieving an MVR of less than 31 cm 3 /10 min and an HDT of greater than 185°C at 0.45 MPa and an HDT of greater than 132°C at 1.8 MPa.
  • Example 7 shows increases to HDT and tensile properties in conjunction with a lower MVR, which demonstrates an improvement in viscosity that was achieved by using PPS-E with PEI in the two-pass method compared to a composition of PEI, PPS, and ECN prepared using a one-pass method (Example 5).
  • Examples 9 to 13 The purpose of Examples 9 to 13 was to demonstrate the effect of ECN- compatibilized PPS (PPS-E) in compositions including poly(sulfone etherimide) (PSEI) instead of PEI when prepared according to the two-pass method. Compositions were prepared and tested in accordance with the procedures described above. Compositions and properties for Examples 9 to 13 are shown in Table 3.
  • PPS-E ECN- compatibilized PPS
  • PSEI poly(sulfone etherimide)
  • Example 11 uses the PPS-E as prepared in Example 3. Accordingly, the compatibilized polyphenylene sulfide composition (PPS-E) in Example 11 is a melt blended combination of 98 wt% of PPS and 2 wt% of ECN.
  • Examples 14 to 18 The purpose of Examples 14 to 18 was to demonstrate the effect of adding silicon-containing particles to the composition including ECN-compatibilized PPS (PPS-E) and PEI when prepared according to the two-pass method. Compositions were prepared and tested in accordance with the procedures described above. Compositions and properties for Examples 14 to 18 are shown in Table 4.
  • Example 18 uses the PPS-E as prepared in Example 3. Accordingly, the compatibilized polyphenylene sulfide composition (PPS-E) in Example 18 is a melt blended combination of 98 wt% of PPS and 2 wt% of ECN.
  • PPS-E compatibilized polyphenylene sulfide composition
  • a compatibilized composition comprising: a polyimide; and a compatibilized polyarylene sulfide composition comprising a melt blended combination of an epoxy novolac resin and a polyarylene sulfide, wherein the compatibilized composition does not comprise a polyphenylene sulfone.
  • Aspect 2 The compatibilized composition of Aspect 1, comprising 10 to 90 wt% of the polyimide and 10 to 90 wt% of the compatibilized polyarylene sulfide composition, wherein each weight percent is based on the total weight of the compatibilized composition.
  • Aspect 3 The compatibilized composition of Aspect 1 or Aspect 2, wherein the polyimide is present in an amount of 20 to 80 wt%, preferably 30 to 70 wt%, based on the total weight of the compatibilized composition; and the compatibilized polyarylene sulfide composition is prepared from the melt blended combination of: 80 to 99 wt%, preferably 85 to 98 wt%, more preferably 90 to 98 wt% of the polyarylene sulfide, and 1 to 20 wt%, preferably 2 to 15 wt%, more preferably 2 to 10 wt% of the epoxy novolac resin, each based on the total weight of the compatibilized polyarylene sulfide composition.
  • Aspect 4 The compatibilized composition of any one of the preceding Aspects, wherein the polyimide is a polyetherimide, a poly(sulfone etherimide), or a combination thereof.
  • Aspect 5 The compatibilized composition of any one of the preceding Aspects, wherein the epoxy novolac resin is an epoxy phenol novolac resin, an epoxy cresol novolac resin, or a combination thereof.
  • Aspect 6 The compatibilized composition of any one of the preceding Aspects, wherein the compatibilized composition has at least one of: a tensile modulus of 3550 to 5000 MPa, preferably 3650 to 4500 MPa, as determined according to ISO-527; a heat deflection temperature of greater than or equal to 180 to 220°C, preferably 185 to 210°C, as determined according to ISO-75 at a pressure of 0.45 MPa; a heat deflection temperature of 130 to 200°C, preferably 132 to 190°C, as determined according to ISO-75 at a pressure of 1.8 MPa; an impact strength of greater than or equal to 4.5 kJ/m 2 , preferably greater than or equal to 4.6 kJ/m 2 , as determined according to ISO-180; or an elongation at break of greater than or equal to 40%, preferably greater than or equal to 50%, as determined according to ISO-527.
  • a tensile modulus 3550 to 5000 MPa, preferably 3650 to 4
  • Aspect 7 The compatibilized composition of any one of the preceding Aspects, wherein the heat deflection temperature and the tensile modulus of the compatibilized composition are greater than a heat deflection temperature and a tensile modulus of a comparable composition, wherein the comparable composition comprises a same amount of the polyimide, a same amount of the polyarylene sulfide, and a same amount of the epoxy novolac resin as the compatibilized composition, and wherein the polyarylene sulfide and the epoxy novolac resin are not melt blended as a compatibilized polyarylene sulfide composition in the comparable composition.
  • Aspect 8 The compatibilized composition of any one of the preceding Aspects, wherein the morphology of the compatibilized composition comprises a domain size that is less than a domain size of a comparable composition, wherein the comparable composition comprises a same amount of the polyimide, a same amount of the polyarylene sulfide, and a same amount of the epoxy novolac resin as the compatibilized composition, and wherein the polyarylene sulfide and the epoxy novolac resin are not melt blended as a compatibilized polyarylene sulfide composition in the comparable composition.
  • Aspect 9 The compatibilized composition of any one of the preceding Aspects, further comprising a particulate material, preferably wherein the particulate material is fumed silica, fused silica, precipitated silica, silica gel, polysilsesquioxane, quartz, diatomaceous earth, milled glass, glass spheres, or a combination thereof.
  • Aspect 10 The compatibilized composition of any one of Aspects 1 to 8, comprising: 35 to 50 wt% of a polyetherimide; and 50 to 65 wt% of the compatibilized polyarylene sulfide composition, wherein the compatibilized composition does not comprise a particulate material or a glass fiber, wherein the compatibilized composition has a melt volume flow rate of 25 to 35 cm 3 /10 min, as determined according to ISO-1133 at 360°C/5 kg, an elongation at break of greater than or equal to 55%, as determined according to ISO-527, and at least one of: a heat deflection temperature of greater than or equal to 180°C, as determined according to ISO-75 at a pressure of 0.45 MPa, or a heat deflection temperature of greater than or equal to 130°C, as determined according to ISO-75 at a pressure of 1.8 MPa, and wherein each weight percent is based on the total weight of the compatibilized composition.
  • Aspect 11 The compatibilized composition of any one of Aspects 1 to 8, comprising: 30 to 55 wt% of a poly(sulfone etherimide); and 45 to 70 wt% of the compatibilized polyarylene sulfide composition, wherein the compatibilized composition does not comprise a particulate material or a glass fiber, wherein the compatibilized composition has a melt volume flow rate of 25 to 40 cm 3 /10 min, as determined according to ISO-1133 at 360°C/5 kg, an elongation at break of greater than or equal to 50%, as determined according to ISO-527, and at least one of a heat deflection temperature of greater than 180°C, as determined according to ISO-75 at a pressure of 0.45 MPa, or a heat deflection temperature of greater than or equal to 135°C, as determined according to ISO-75 at a pressure of 1.8 MPa, and wherein each weight percent is based on the total weight of the compatibilized composition.
  • Aspect 12 The compatibilized composition of any one of Aspects 1 to 9, comprising: 30 to 55 wt% of a polyetherimide 45 to 70 wt% of the compatibilized polyarylene sulfide composition; and 1 to 6 wt% of a particulate material, wherein the compatibilized composition has at least one of a heat deflection temperature of greater than 185°C, as determined according to ISO-75 at a pressure of 0.45 MPa, or a heat deflection temperature of greater than or equal to 130°C, as determined according to ISO-75 at a pressure of 1.8 MPa, and wherein each weight percent is based on the total weight of the compatibilized composition.
  • Aspect 13 A method of manufacturing the compatibilized composition of any one of preceding Aspects, the method comprising: melt- mixing the epoxy novolac resin and the polyarylene sulfide to form the compatibilized polyarylene sulfide composition; and melt mixing the compatibilized polyarylene sulfide composition and the polyimide to form the compatibilized composition, preferably wherein the melt-mixing to form the compatibilized composition is at a temperature of 250 to 360°C.
  • Aspect 14 The method of Aspect 13, wherein the melt-mixing to form the compatibilized polyarylene sulfide composition is a first pass through an extruder and the melt mixing to form the compatibilized composition is a second pass through the extruder.
  • Aspect 15 An article comprising the compatibilized composition of any one of the preceding Aspects, preferably wherein the article is a molded article.
  • compositions, methods, and articles can alternatively comprise, consist of, or consist of, any appropriate materials, steps, or components herein disclosed.
  • the compositions, methods, and articles can additionally, or alternatively, be formulated to be devoid, or substantially free, of any materials (or species), steps, or components, that are otherwise not necessary to the achievement of the function or objectives of the compositions, methods, and articles.
  • test standards are the most recent standard in effect as of the filing date of this application, or, if priority is claimed, the filing date of the earliest priority application in which the test standard appears.
  • hydrocarbyl includes groups containing carbon, hydrogen, and optionally one or more heteroatoms (e.g., 1, 2, 3, or 4 atoms such as halogen, O, N, S, P, or Si).
  • heteroatoms e.g., 1, 2, 3, or 4 atoms such as halogen, O, N, S, P, or Si.
  • Alkyl means a branched or straight chain, saturated, monovalent hydrocarbon group, e.g., methyl, ethyl, i-propyl, and n-butyl.
  • Alkylene means a straight or branched chain, saturated, divalent hydrocarbon group (e.g., methylene (-CH2-) or propylene (-(CH2)3-)).
  • Alkynyl means a straight or branched chain, monovalent hydrocarbon group having at least one carbon-carbon triple bond (e.g., ethynyl).
  • Alkoxy means an alkyl group linked via an oxygen (i.e., alkyl-O-), for example methoxy, ethoxy, and sec-butyloxy.
  • Cycloalkyl and “cycloalkylene” mean a monovalent and divalent cyclic hydrocarbon group, respectively, of the formula -CnFhn-x and -C n H2n-2x- wherein x is the number of cyclization(s).
  • Aryl means a monovalent, monocyclic, or polycyclic aromatic group (e.g., phenyl or naphthyl).
  • Arylene means a divalent, monocyclic, or polycyclic aromatic group (e.g., phenylene or naphthylene).
  • Arylene means a divalent aryl group.
  • Alkylaryl means an aryl group substituted with an alkyl group.
  • Arylalkyl means an alkyl group substituted with an aryl group (e.g., benzyl).
  • halo means a group or compound including one more halogen (F, Cl, Br, or I) substituents, which can be the same or different.
  • hetero means a group or compound that includes at least one ring member that is a heteroatom (e.g., 1, 2, or 3 heteroatoms, wherein each heteroatom is independently N, O, S, or P.
  • each of the foregoing groups can be unsubstituted or substituted, provided that the substitution does not significantly adversely affect synthesis, stability, or use of the compound.

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Abstract

Une composition compatible, comprenant : un polyimide; et une composition de poly(sulfure d'arylène) compatible comprenant une combinaison mélangée à l'état fondu d'une résine novolaque époxy et d'un poly(sulfure d'arylène), la composition compatible ne comprenant pas de polyphénylène sulfone.
PCT/IB2020/059986 2019-11-11 2020-10-23 Composition de polymère à haute température compatible WO2021094858A1 (fr)

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Citations (8)

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US4690997A (en) 1984-01-26 1987-09-01 General Electric Company Flame retardant wire coating compositions
US4808686A (en) 1987-06-18 1989-02-28 General Electric Company Silicone-polyimides, and method for making
EP0697442A1 (fr) * 1994-08-09 1996-02-21 General Electric Company Mélanges de résins de poly(arylènesulfide) et polyétherimide modifiées par des époxides
US20130079438A1 (en) * 2011-09-27 2013-03-28 Sabic Innovative Plastics Ip B.V. Blends of polyetherimide sulfone and poly(arylene sulfide)
US20130079459A1 (en) * 2011-09-27 2013-03-28 Sabic Innovative Plastics Ip B.V. Blends of polyetherimide sulfone and poly(arylene sulfide) and methods of making
US20140194556A1 (en) * 2013-01-04 2014-07-10 Sabic Innovative Plastics Ip B.V. Blends of polyphenylene sulfones and polyphenylene sulfide resins
US20140194580A1 (en) * 2013-01-04 2014-07-10 Sabic Innovative Plastics Ip B.V. Blends of polysulfones and polyphenylene sulfide resins

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Publication number Priority date Publication date Assignee Title
US8618218B2 (en) * 2011-09-27 2013-12-31 Sabic Innovative Plastics Ip B.V. Blends of polysiloxane/polyimide block copolymer and poly(arylene sulfide)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4404350A (en) 1982-07-07 1983-09-13 General Electric Company Silicone-imide copolymers and method for making
US4690997A (en) 1984-01-26 1987-09-01 General Electric Company Flame retardant wire coating compositions
US4808686A (en) 1987-06-18 1989-02-28 General Electric Company Silicone-polyimides, and method for making
EP0697442A1 (fr) * 1994-08-09 1996-02-21 General Electric Company Mélanges de résins de poly(arylènesulfide) et polyétherimide modifiées par des époxides
US20130079438A1 (en) * 2011-09-27 2013-03-28 Sabic Innovative Plastics Ip B.V. Blends of polyetherimide sulfone and poly(arylene sulfide)
US20130079459A1 (en) * 2011-09-27 2013-03-28 Sabic Innovative Plastics Ip B.V. Blends of polyetherimide sulfone and poly(arylene sulfide) and methods of making
US20140194556A1 (en) * 2013-01-04 2014-07-10 Sabic Innovative Plastics Ip B.V. Blends of polyphenylene sulfones and polyphenylene sulfide resins
US20140194580A1 (en) * 2013-01-04 2014-07-10 Sabic Innovative Plastics Ip B.V. Blends of polysulfones and polyphenylene sulfide resins

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