COMPATIBLIZED HIGH HEAT POLYMER COMPOSITION

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of and priority to European Patent Application No. EP19208408.5, filed on November 11, 2019, the entire content of which is incorporated by reference herein.

BACKGROUND

[0001] This disclosure is directed to compatibilized epoxy compositions and methods of forming the compatibilized epoxy compositions.

[0002] There has long been interest in developing 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. However, 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. When a compatible unfilled resin blend is desired, 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.

[0003] 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.

[0004] 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

[0005] Provided is 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).

[0006] 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.

[0007] Also provided is an article including the compatibilized composition, preferably wherein the article is a molded article.

[0008] The above described and other features are exemplified by the following drawings and detailed description.

BRIEF DESCRIPTION OF THE DRAWINGS

[0009] The following figures are exemplary aspects of the disclosure.

[0010] FIG. 1 is a scanning electron microscope (SEM) image of a comparative composition of polyetherimide (PEI) and polyphenylene sulfide (PPS) without a compatibilizer.

[0011] 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.

[0012] 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.

[0013] FIG. 4 is an SEM image of Example 7, where the composition of PEI and PPS- ECN was prepared by the two-step process.

DETAILED DESCRIPTION

[0014] The present inventors have advantageously discovered that 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. When the polyarylene sulfide, polyimide, and the epoxy novolac resin are instead meld blend together without first preparing the compatibilizer in a separate step, these improved properties are not obtained. In addition, the present inventors discovered these improved properties can be achieved when the compatibilized composition does not include a polyphenylene sulfone. Polyphenylene sulfone (also known as “PPSU”) is a poly(arylene ether-sulfone) which contains units, for example at least 60 wt%, or at least 75 wt%, or at least 85 wt% structural units of the formula:

[0015] Accordingly, 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. It is to be understood that 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.

[0016] 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. Exemplary aromatic hydrocarbon groups include any of those of the formulas wherein clic, acyclic, aromatic, or non-aromatic, -P(R ^a )(=0)- wherein R ^a is a Ci-s alkyl or C _6-12 aryl, -C _y th _y - wherein y is an integer from 1 to 5 or a halogenated derivative thereof (which includes perfluoroalkylene groups), or a group of the formula -O-Z-O- as described in formula (3) below. [0017] 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. In an aspect R is m- phenylene, p-phenylene, or a diaryl sulfone.

[0018] 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). In the poly(sulfone etherimide) of the present disclosure, at least some groups R in Formula (3) are a sulfone group (-SO2-) .

[0019] Further in formula (3), 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). In a specific aspect Z is a derived from bisphenol A, such that Q in formula (3a) is 2,2-isopropylidene.

[0020] In an aspect in formula (3), R is m-phenylene or p-phenylene and T is -O-Z-O- wherein Z is a divalent group of formula (4a). Alternatively, 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.

[0021] In some aspects, the polyetherimide can be a copolymer, for example, a polyetherimide sulfone copolymer comprising structural units of formula (1) wherein at least 50 mole% of the R groups are of formula (2) wherein Q ¹ is -SO2- and the remaining R groups are independently p-phenylene or m-phenylene or a combination thereof; and Z is 2,2’ -(4- phenylene)isopropylidene.

[0022] Alternatively, the polyetherimide copolymer optionally comprises additional structural imide units, for example imide units of formula (1) wherein R and V are as described in formula (1), for example V is wherein W is a single bond, ydrocarbon moiety that can be cyclic, acyclic, aromatic, or non-aromatic, -P(R ^a )(=0)- wherein R ^a is a Ci-s alkyl or C6-12 aryl, or -C _y th _y - wherein y is an integer from 1 to 5 or a halogenated derivative thereof (which includes perfluoroalkylene groups). These 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.

[0023] The polyimide and polyetherimide can be prepared by any of the methods well known to those skilled in the art, including the reaction of an aromatic bis(ether anhydride) of formula (5a) or formula (5b) or a chemical equivalent thereof, with an organic diamine of formula (6)

H2N-R-NH2 (6) wherein V, T, and R are defined as described above. 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.

[0024] Illustrative examples of 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)benzophenone dianhydride; 4,4'-bis(2,3- dicarboxyphenoxy)diphenyl sulfone dianhydride; 4-(2,3-dicarboxyphenoxy)-4'-(3,4- dicarboxyphenoxy)diphenyl-2, 2-propane dianhydride; 4-(2,3-dicarboxyphenoxy)-4'-(3,4- dicarboxyphenoxy)diphenyl ether dianhydride; 4-(2,3-dicarboxyphenoxy)-4'-(3,4- dicarboxyphenoxy)diphenyl sulfide dianhydride; 4-(2,3-dicarboxyphenoxy)-4'-(3,4- dicarboxyphenoxy)benzophenone dianhydride; and, 4-(2,3-dicarboxyphenoxy)-4'-(3,4- dicarboxyphenoxy)diphenyl sulfone dianhydride, as well as various combinations thereof.

[0025] Examples of 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-aminocyclohexyl) methane, m-phenylenediamine, p- phenylenediamine, 2,4-diaminotoluene, 2,6-diaminotoluene, m-xylylenediamine, p- xylylenediamine, 2-methyl-4, 6-diethyl- 1 ,3-phenylene-diamine, 5-methyl-4, 6-diethyl- 1,3- phenylene-diamine, benzidine, 3,3’-dimethylbenzidine, 3,3’-dimethoxybenzidine, 1,5- diaminonaphthalene, bis(4-aminophenyl) methane, bis(2-chloro-4-amino-3,5-diethylphenyl) methane, bis(4-aminophenyl) propane, 2,4-bis(p-amino-t-butyl) toluene, bis(p-amino-t- butylphenyl) ether, bis(p-methyl-o-aminophenyl) benzene, bis(p-methyl-o-aminopentyl) benzene, 1, 3-diamino-4-isopropylbenzene, bis(4-aminophenyl) sulfide, bis-(4-aminophenyl) sulfone (also known as 4,4'-diaminodiphenyl sulfone (DDS)), and bis(4-aminophenyl) ether.

Any regioisomer of the foregoing compounds can be used. Combinations of these compounds can also be used. In some aspects the organic diamine is m-phenylenediamine, p- phenylenediamine, 4,4'-diaminodiphenyl sulfone, or a combination thereof.

[0026] 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. For example, 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. Combinations of the foregoing R groups can be used in the same copolymer. In an aspect, the polysiloxane blocks comprises R’ groups that have minimal hydrocarbon content. In a specific aspect, an R’ group with a minimal hydrocarbon content is a methyl group. [0027] 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. In an aspect, 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.

[0028] In some poly(siloxane-etherimide)s 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. Alternatively, 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. Thus, the poly(siloxane-imide) copolymer can be a block, random, or graft copolymer. In an aspect, the copolymer is a block copolymer.

[0029] Examples of specific poly(siloxane-etherimide)s are described in US Pat. Nos. 4,404,350, 4,808,686 and 4,690,997. In an aspect, 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. In a specific embodiment of the poly(siloxane-etherimide), 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, and each R’ of the siloxane is methyl.

[0030] 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. In particular, as mentioned above, 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. In an aspect, 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).

[0031] The polyimides and polyetherimides (including poly(sulfone etherimides) 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. In some aspects, 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. In some aspects 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.

[0032] The polyimide, such as the polyetherimide or the poly(sulfone etherimide), can be present in an amount of 10 to 90 weight percent (wt%), based on the total weight of the compatibilized composition. For example, the polyimide can be present in an amount of 20 to 80 wt%, or preferably 30 to 70 wt%, based on the total weight of the compatibilized composition.

[0033] In addition to the polyimide, such as the polyetherimide or poly(sulfone etherimide), 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.

[0034] 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 atoms. The other 30 mol% or less, and preferably 10 mol% or less, of the repeating structural units of PPS can be those of the following structural formulae

[0035] 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.

[0036] The PPS can be prepared using methods that are known in the art. By way of example, 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.

[0037] The alkali metal sulfide can be, for example, lithium sulfide, sodium sulfide, potassium sulfide, rubidium sulfide, cesium sulfide or a mixture thereof. When 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. In addition, 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.

[0038] 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. Specific dihaloaromatic compounds include p-dichlorobenzene, m-dichlorobenzene, o-dichlorobenzene, 2,5-dichlorotoluene, 1,4-dibromobenzene, l-methoxy-2, 5 -dichlorobenzene, and 3,5- dichlorobenzoic acid. [0039] Alternatively, an aromatic group besides phenylene can be used to provide the polyarylene sulfide. 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. Specific dihaloaromatic compounds include 1,4-dichloronaphthalene, 4,4'-dichlorobiphenyl, 4,4'-dichlorodiphenyl ether, 4,4'-dichlorodiphenylsulfone, 4,4'- dichlorodiphenylsulfoxide, and 4,4'-dichlorodiphenyl ketone.

[0040] Optionally, a monohalo compound (not necessarily an aromatic compound) can be used in combination with the dihaloaromatic compound to provide end groups of the polyarylene sulfide or to regulate the polymerization reaction and/or the molecular weight of the polyarylene sulfide. Exemplary end groups include, for example, halogen, thiol, or hydroxy.

[0041] The process for manufacturing PPS can include carrying out the polymerization reaction in an organic amide solvent. Exemplary 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.

[0042] 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. In a second polymerization step, water is added to the reaction slurry and the reaction mixture is heated at 250 to 290°C and the polymerization can continue until the melt viscosity of the thus formed polymer is raised to the desired final level of the polyphenylene sulfide or polyarylene sulfide. The duration of the second polymerization step can be, e.g., from 0.5 to 20 hours.

[0043] 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. For some product applications, it is preferred to have a low impurity level in the PPS. 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.

[0044] Though the 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.

[0045] 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.

[0046] In addition to the PPS, 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.

[0047] 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. In a specific aspect, 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.

[0048] Without being bound by theory it is believed that 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.

[0049] The epoxy novolac resin can be made by reacting a phenol with formaldehyde. The term "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.

[0050] 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. [0051] 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.

[0052] For example, the epoxy novolac resin can be an epoxy phenol novolac (EPN) resin, an epoxy cresol novolac (ECN) resin, or a combination thereof. For example, the epoxy novolac resin can include units of formula (11) wherein m is 0 or 1. In a specific aspect, the epoxy novolac resin preferably comprises an epoxy o-cresol novolac resin. For example, 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.

[0053] In some aspects, epoxy-containing materials other than the epoxy novolac resin can be excluded from the composition. For example, the composition can exclude epoxy- functionalized styrenic polymers such as epoxy-functionalized styrene acrylate oligomers.

[0054] 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. For example, 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.

[0055] 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. In a specific aspect, 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. In another specific aspect, 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.

[0056] The compatibilized composition can optionally further include one or more additives, with the proviso that any additive does not significantly adversely affect the desired properties of the compatibilized composition. Exemplary additives can include, for example, electrically conductive fillers, reinforcing fillers, stabilizers, lubricants, mold release agents, inorganic pigments, UV absorbers, antioxidants, plasticizers, anti-static agents, foaming agents, blowing agents, metal deactivators, and combinations comprising one or more of the foregoing. Examples of electrically conductive fillers include conductive carbon black, carbon fibers, metal fibers, metal powder, carbon nanotubes, and the like, and combinations comprising any one of the foregoing electrically conductive fillers. Examples of reinforcing fillers 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. In some aspects, phosphorus containing stabilizers with a molecular weight greater than or equal to 500 are useful. Phosphorus containing stabilizers are typically present in the composition at 0.05-0.5% by weight of the formulation. Flow aids and mold release compounds are also contemplated.

[0057] In some aspects, 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. In some aspects, the particle size can be 0.1 to 20 mhi, for example 0.5 to 15 mhi. In other aspects, 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. For example, 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. In other aspects, the compatibilized composition does not comprise a particulate material, conductive filler, or reinforcing filler. For example, in some aspects the compatibilized composition does not include a particulate material or a glass fiber.

[0058] Each composition can be prepared by melt-blending or melt-kneading the components of that composition. The melt-blending or melt-kneading can be performed using common equipment such as ribbon blenders, HENSCHEL mixers, BANBURY mixers, drum tumblers, single-screw extruders, twin-screw extruders, multi-screw extruders, co-kneaders, or the like. For example, 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. Preferably, steps a) and b) can be conducted at a temperature of 250 to 360°C. In some aspects, 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.

[0059] The compatibilized composition can have a tensile modulus of 3550 to 5000 MPa, preferably 3650 to 4500 MPa, as determined according to ISO-527.

[0060] 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.

[0061] The compatibilized composition can have 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.

[0062] 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.

[0063] In some aspects, 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. As used, herein, 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. [0064] In an aspect, the morphology of the compatibilized composition has a domain size that is less than a domain size of a comparable composition. The comparable composition is as defined herein. 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.

[0065] In an aspect, 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. In this aspect, the polyimide is a polyetherimide, a poly(sulfone etherimide), or a combination thereof; and the epoxy novolac resin is an epoxy phenol novolac resin, an epoxy cresol novolac resin, or a combination thereof. In this aspect, 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.

[0066] In a particular aspect, the compatibilized composition includes 35 to 50 wt% of a polyetherimide, 50 to 65 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 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, 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, and 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.

[0067] In a particular aspect, 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.

[0068] In a particular aspect, the compatibilized composition includes 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, and the compatibilized composition has a heat deflection temperature of greater than 185°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 130°C, as determined according to ISO-75 at a pressure of 1.8 MPa.

[0069] 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.

[0070] 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.

[0071] This disclosure is further illustrated by the following examples, which are non limiting.

EXAMPLES

[0072] Materials used in the following Examples are described in Table 1.

Table 1

[0073] 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.

[0074] Heat deflection temperature (HDT) was measured flat on an 80 mmxlO mmx4 mm injection molded bar with a 64 mm span at 0.45 or 1.8 MPa according to ISO 75/Bf and ISO 75/Af. Melt flow rate (MFR) was measured in accordance with ISO 1133 at 337°C or 367°C using a 6.6 kg load. Melt volume flow rate (MVR) was measured at 360°C/5 kg with a 300 second dwell time according to ISO 1133. Tensile properties (tensile modulus, tensile stress at break, tensile stress at yield) were measured in accordance with ISO 527 with a speed of 50 mm/min and are reported in megapascal (MPa). Maximum tensile stress is labeled as stress at UTS. Elongation at break was measured in accordance with ISO 527 and reported as percent elongation (%). Izod notched and unnotched impact were measured at 23°C according to ISO 180/1A and ISO 180/1U using a multipurpose test specimen in accordance with ISO 3167. Impact is reported as kilojoules per square meter (kJ/m ² ). Glass transition temperature (T _g , °C) was determined by differential scanning calorimetry. The parallel to flow (flow) and transverse to flow (xflow) coefficients of linear thermal expansion (CTE) were measured according to ISO 11359-2, from 0 to 80°C at a speed of 5°C/min.

Examples 1 to 8

[0075] 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

*Denotes a comparative example.

[0076] 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. For convenience, 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.

[0077] These examples 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. In addition, 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

[0078] 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.

Table 3

*Denotes a comparative example.

[0079] 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.

[0080] These examples show that a composition including PSEI/PPS/ECN (Comparative Example 10) has improved HDT compared to a composition including PEI/PPS/ECN (Comparative Example 9) when both are prepared by the one-pass method. These examples also demonstrate that the ECN-modified polyphenylene sulfide (PPS-E) in combination with PSEI (Example 11) provides a composition capable of achieving further increased HDT, tensile modulus, and elongation at break, and a decreased MVR. It is further noted that incorporation of 45 wt% of glass fibers (Comparative Examples 12 and 13) into the PEI/PPS/ECN blend (Comparative Example 9) and the PSEI/PPS/ECN blend (Comparative Example 10), respectively, also provided substantial increases to HDT and tensile modulus.

Examples 14 to 18

[0081] 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.

Table 4

*Denotes a comparative example.

[0082] 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.

[0083] These examples demonstrate that the addition of Particle- 1 or Particle-2 to the compositions including PEI/PPS/ECN prepared by the one-pass method (Comparative Examples 15 and 16) provided increased HDT (Example 14). Incorporation of both Particle-1 and Particle- 2 into the composition including PEI/PPS/ECN prepared by the one-pass method (Comparative Example 17) further increased HDT without a significant decrease in mechanical properties. The composition including the ECN-modified polyphenylene sulfide (PPS-E) in combination with PEI prepared by the two-pass method (Example 18) achieved a further increase to HDT and improvements to mechanical properties.

[0084] This disclosure further encompasses the following Aspects.

[0085] Aspect 1. 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.

[0086] 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.

[0087] 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. [0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] 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. [0099] Aspect 15. An article comprising the compatibilized composition of any one of the preceding Aspects, preferably wherein the article is a molded article.

[0100] The 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.

[0101] All ranges disclosed herein are inclusive of the endpoints, and the endpoints are independently combinable with each other (e.g., ranges of “up to 25 wt%, or 5 to 20 wt%”, is inclusive of the endpoints and all intermediate values of the ranges of “5 to 25 wt%,” etc.). “Combinations” is inclusive of blends, mixtures, alloys, reaction products, and the like. The terms “first,” “second,” and the like, do not denote any order, quantity, or importance, but rather are used to distinguish one element from another. The terms “a” and “an” and “the” do not denote a limitation of quantity and are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. “Or” means “and/or” unless clearly stated otherwise. Reference throughout the specification to “some aspects”, “an aspect”, and so forth, means that a particular element described in connection with the aspect is included in at least one aspect described herein, and may or may not be present in other aspects. In addition, it is to be understood that the described elements may be combined in any suitable manner in the various aspects. A “combination thereof’ is open and includes any combination including at least one of the listed components or properties optionally together with a like or equivalent component or property not listed.

[0102] Unless specified to the contrary herein, all 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.

[0103] Unless defined otherwise, technical and scientific terms used herein have the same meaning as is commonly understood by one of skill in the art to which this application belongs. All cited patents, patent applications, and other references are incorporated herein by reference in their entirety. However, if a term in the present application contradicts or conflicts with a term in the incorporated reference, the term from the present application takes precedence over the conflicting term from the incorporated reference.

[0104] Compounds are described using standard nomenclature. For example, any position not substituted by any indicated group is understood to have its valency filled by a bond as indicated, or a hydrogen atom. A dash ("-") that is not between two letters or symbols is used to indicate a point of attachment for a substituent. For example, -CHO is attached through carbon of the carbonyl group.

[0105] As used herein, the term “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). "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-)). “Alkenyl” and “alkenylene” mean a monovalent or divalent, respectively, straight or branched chain hydrocarbon group having at least one carbon-carbon double bond (e.g., ethenyl (- HC=CH2) or propenylene (-H(3(ϋ¾)=ϋ42-). “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). The prefix "halo" means a group or compound including one more halogen (F, Cl, Br, or I) substituents, which can be the same or different. The prefix “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.

[0106] Unless substituents are otherwise specifically indicated, 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. “Substituted” means that the compound or group is substituted with at least one (e.g., 1, 2, 3, or 4) substituents that can each independently be a C1-9 alkoxy, a C1-9 haloalkoxy, a nitro (-NO2), a cyano (-CN), a Ci- ₆ alkyl sulfonyl (-S(=0) ₂ -alkyl), a C6-12 aryl sulfonyl (-S(=0) ₂ -aryl)a thiol (-SH), a thiocyano (-SCN), a tosyl (CH3C6H4SO2-), a C3-12 cycloalkyl, a C2-12 alkenyl, a C5-12 cycloalkenyl, a C6-12 aryl, a C7-13 arylalkylene, a C4-12 heterocycloalkyl, and a C3-12 heteroaryl instead of hydrogen, provided that the substituted atom’s normal valence is not exceeded. When a compound is substituted, the indicated number of carbon atoms is the total number of carbon atoms in the compound or group, including those of any substituents.

[0107] While particular aspects have been described, alternatives, modifications, variations, improvements, and substantial equivalents that are or may be presently unforeseen may arise to applicants or others skilled in the art. Accordingly, the appended claims as filed and as they may be amended are intended to embrace all such alternatives, modifications variations, improvements, and substantial equivalents.