WO2020058790A1 - Revêtement pour fil électrique comprenant une composition thermoplastique - Google Patents

Revêtement pour fil électrique comprenant une composition thermoplastique Download PDF

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Publication number
WO2020058790A1
WO2020058790A1 PCT/IB2019/057349 IB2019057349W WO2020058790A1 WO 2020058790 A1 WO2020058790 A1 WO 2020058790A1 IB 2019057349 W IB2019057349 W IB 2019057349W WO 2020058790 A1 WO2020058790 A1 WO 2020058790A1
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poly
sulfone
thermoplastic composition
electrical wire
phenylene
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PCT/IB2019/057349
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English (en)
Inventor
Mian DAI
Fen Zhang
Liang Shen
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Sabic Global Technologies B.V.
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Publication of WO2020058790A1 publication Critical patent/WO2020058790A1/fr

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/42—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes polyesters; polyethers; polyacetals
    • H01B3/427—Polyethers
    • 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
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/20—Polysulfones
    • C08G75/23—Polyethersulfones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • 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
    • C08L81/06—Polysulfones; Polyethersulfones
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/301—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen or carbon in the main chain of the macromolecule, not provided for in group H01B3/302
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/303—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 H01B3/38 or H01B3/302
    • H01B3/306—Polyimides or polyesterimides
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/36—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes condensation products of phenols with aldehydes or ketones

Definitions

  • Aromatic polyketones are crystalline or semi-crystalline polymers valued due to their resistance to high temperatures, crystallizability, melt extrudability, and injection moldability.
  • aromatic polyketones such as polyaryletherketones frequently suffer from brittleness, e.g., poor toughness (low ductility), making them unsuitable for many applications.
  • Blends of polyaryletherketones with other polymers have sought to solve this problem, but these blends have suffered from drawbacks such as delamination, insufficient heat resistance, and the like. Accordingly, there remains a need in the art for compatible
  • compositions that exhibit the high temperature performance features of polyaryletherketone and also exhibits improved ductility properties.
  • An electrical wire comprising: an electrically conductive wire; and a covering disposed over the electrically conductive wire, wherein the covering comprises a thermoplastic composition that comprises, based on the total weight of the thermoplastic composition: 5 to 90 wt.% of a poly(arylene ether ketone); 5 to 90 wt% of a poly(arylene ether sulfone); and 5 to 50 wt% of a poly(etherimide).
  • thermoplastic composition comprising, based on the total weight of the thermoplastic composition: 5 to 90 wt.% of a poly(arylene ether ketone); 5 to 90 wt.% of a poly(arylene ether sulfone); and 5 to 50 wt.% of a poly(etherimide) having a glass transition temperature of 220 to 320°C, preferably 240 to 320°C, more preferably 245 to 3l2°C, determined by differential scanning calorimetry (DSC) as per ASTM D3418 with a 20°C/min heating rate; wherein the thermoplastic composition has one or more of the following properties: a heat deflection temperature of at least l60°C, as measured on a sample with a thickness of 3.2 mm at 1.82 MPa in accordance with ASTM D648; a flexural modulus of 2,000 to 3,000 MPa, determined in accordance with ASTM 790 at 1.27 nr/min; or a flexural strength at
  • thermoplastic compositions comprising a poly(arylene ether ketone), a poly(arylene ether sulfone), and a poly(etherimide).
  • the blends can be useful for the preparation of articles for various industries, including railway vehicle components, automobile components, marine vehicle components, aircraft components, or data transmission components.
  • the inventors hereof have unexpectedly discovered the combination of these three polymers produces a composition having desirable properties for high-heat wire covering applications.
  • poly(arylene ether ketone)s comprise repeating units of formula (1) and repeating units of formula (2)
  • Ar is independently a substituted or unsubstituted, monocyclic or polycyclic aromatic group having 6 to 30 carbons.
  • exemplary Ar groups include, but are not limited to, phenyl, tolyl, naphthyl, and biphenyl.
  • the poly(arylene ether ketone)s can be a poly(ether ketone).
  • Poly(ether ketone)s comprise repeating units of formula (3)
  • Ar is defined as above and Ar 1 is independently at each occurrence a substituted or unsubstituted, monocyclic or polycyclic aromatic group having 6 to 30 carbons.
  • Ar can be the same as or different from Ar 1 .
  • Ar and Ar 1 are phenyl groups, preferably unsubstituted phenyl groups.
  • the poly(arylene ether ketone)s can be a poly(ether ether ketone).
  • Poly(ether ether ketone)s comprise repeating units of formula (4)
  • Ar and Ar 1 are defined as above.
  • Ar 2 is independently at each occurrence a substituted or unsubstituted, monocyclic or polycyclic aromatic group having 6 to 30 carbons.
  • Ar, Ar 1 , and Ar 2 can be the same as or different from each other. Additionally, two of Ar, Ar 1 , and Ar 2 can be the same as each other and the third can be different.
  • Ar, Ar 1 , and Ar 2 are phenyl groups, preferably unsubstituted phenyl groups.
  • the poly(arylene ether ketone)s can also be a poly(ether ketone ketone).
  • Poly(ether ketone ketone)s comprise repeating units of formula (5)
  • Ar and Ar 1 are defined as above.
  • Ar 3 is independently at each occurrence a substituted or unsubstituted, monocyclic or polycyclic aromatic group having 6 to 30 carbons.
  • Ar, Ar 1 , and Ar 3 can be the same as or different from each other. Additionally, two of Ar, Ar 1 , and Ar 3 can be the same as each other and the third can be different.
  • Ar, Ar 1 , and Ar 3 are phenyl groups, preferably unsubstituted phenyl groups.
  • Poly(arylene ether ketone)s are generally known.
  • Examples of commercially available poly(arylene ether ketone)s include those sold under the tradename ZYPEEK 330G, available from Jilin Zhongyan High Performance Plastic Co., Ltd or those sold under the trade name PEEK, available from VICTREX.
  • A“poly(arylene ether sulfone)” as used herein refers to polymers having a backbone of formula (6)
  • Ar 4 , Ar 5 , and Ar 6 are independently at each occurrence a substituted or unsubstituted, monocyclic or polycyclic aromatic group having 6 to 30 carbons.
  • exemplary Ar 4 , Ar 5 , and Ar 6 groups include, but are not limited to, phenyl, tolyl, naphthyl, 2,2-(4-phenylene)isopropylidene, and biphenyl.
  • poly(arylene ether sulfone)s that can be used include polyethersulfone (also known as“PES” or“PESU”), which contains at least 85 wt.% of units of formula (7)
  • polyphenylene sulfone also known as“PPSU) of formula (8)
  • PSU polysulfone
  • poly(arylene ether sulfone)s or a combination thereof poly(arylene ether sulfone)s.
  • Copolymers comprising at least two units of formulas (7), (8), (9), and (10) can also be used.
  • the poly(arylene ether sulfone)s can be linear or branched, having 1 or more, 2 or more, or 5 or more branching points per 1,000 carbon atoms along the polymer chain.
  • the poly(arylene ether sulfone)s are linear, having 10 or fewer, 5 or fewer, 2 or fewer, or 1 or fewer branching points per 1,000 carbon atoms along the polymer chain.
  • the poly(arylene ether sulfone)s have a glass transition temperature (Tg) of greater than l75°C, preferably from 200°C to 280°C, and more preferably from 255 °C to 275°C.
  • the poly(arylene ether sulfone)s can further have a weight average molecular weight (Mw) of 500 to 100,000 grams/mole (g/mol), preferably 1,000 to 75,000 g/mol, more preferably 1,500 to 50,000 g/mol, and still more preferably 2,000 to 25,000 g/mol, determined via GPC using polystyrene standards.
  • Mw weight average molecular weight
  • Exemplary poly(arylene ether sulfone)s that can be used include those that are available from sources such as Solvay Specialty Polymers, Quadrant EPP, Centroplast Centro, Duneon, GEHR Plastics, Westlake Plastics, and Gharda Chemicals.
  • Commercial grades of poly(phenylsulfone)s include those with the trade names RADEL, UDEL, ULTRAS ON, and GAFONE.
  • Polyethersulfones are commercially available from Solvay Advanced Polymers K.K. under the trademark of VERADEL, from BASF Corporation under the trademark of
  • the poly(arylene ether sulfone)s can be present in an amount of 5 to 90 weight percent (wt.%), or 10 to 75 wt.%, or 35 to 55 wt.%, each based on the total weight of the thermoplastic composition.
  • Poly(etherimide)s comprise more than 1, for example 2 to 1000, or 5 to 500, or 10 to 100 stmctural units of formula (11)
  • each R is independently the same or different, and is a substituted or unsubstituted divalent organic group, such as a substituted or unsubstituted C 6 -20 aromatic hydrocarbon group, a substituted or unsubstituted straight or branched chain C4-20 alkylene group, a substituted or unsubstituted C3-8 cycloalkylene group, in particular a halogenated derivative of any of the foregoing.
  • R is divalent group of one or more of the following formulas
  • R is m-phenylene, p-phenylene, or a diarylene sulfone, in particular bis(4,4’- phenylene)sulfone, bis(3, 4’ -phenylene) sulfone, bis(3, 3’-phenylene) sulfone, or a combination thereof.
  • At least 10 mole percent or at least 50 mole percent of the R groups contain sulfone groups such as in particular bis(4,4’-phenylene)sulfone, bis(3,4’- phenylene)sulfone, bis(3,3’-phenylene)sulfone, with the remainder of the R groups, if present, being is m-phenylene or p-phenylene.
  • 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, and Z is an aromatic C 6 -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 of formula (13)
  • R a and R b are each independently 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- ubstituted aromatic groups, where the bridging group and the hydroxy substituent of each C 6 arylene group are disposed ortho, meta, or para (preferably para) to each other on the C 6 arylene group.
  • the bridging group X a can be a single bond, -O-, -S-, -S(O)-, -S(0) 2 -, -C(O)-, or a Ci-ig organic bridging group.
  • the Ci-i 8 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 C1-18 organic group can be disposed such that the CV > 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 (13a)
  • Z is a derived from bisphenol A, such that Q in formula (13a) is 2,2-isopropylidene.
  • R is m-phenylene, p-phenylene, or a combination thereof, and T is -O-Z-O- wherein Z is a divalent group of formula (l3a).
  • R is m-phenylene, p-phenylene, or a combination thereof
  • T is -O-Z-O wherein Z is a divalent group of formula (l3a) and Q is 2,2-isopropylidene.
  • the poly(etherimide)s are poly(etherimide) sulfones having more than 1, for example 2 to 1000, or 5 to 500, or 10 to 100 stmctural units of formula (11), wherein at least 10 mole percent or at least 50 mole percent of the R groups contain sulfone groups.
  • At least 10 mole percent or at least 50 mole percent of the R groups contain sulfone groups in particular bis(4,4’-phenylene)sulfone, bis(3,4’-phenylene)sulfone, bis(3,3’- phenylene)sulfone, or a combination thereof, with the remainder of the R groups, if present, being is m-phenylene or p-phenylene.
  • T is as defined herein, and preferably T is -O-Z-O-, wherein Z is a divalent group of formula (l3a), for example, 2,2-(4-phenylene)isopropylidene, i.e., a bisphenol A moiety.
  • poly(etherimide)s can be prepared by any of the methods known to those skilled in the art, including the reaction of an aromatic bis(ether anhydride) of formula (14) or a chemical equivalent thereof, with an organic diamine of formula (15) (14) H2N-R-NH2 (15)
  • Copolymers of the poly(etherimide)s can be manufactured using a combination of an aromatic bis(ether anhydride) of formula (14) and an additional bis(anhydride) that is not a bis(ether anhydride), for example pyromellitic dianhydride or bis(3,4-dicarboxyphenyl) sulfone dianhydride.
  • aromatic bis(ether anhydride)s include 2,2-bis[4-(3,4- dicarboxyphenoxy)phenyl]propane dianhydride (also known as bisphenol A dianhydride or BPADA), 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; 4,4'-bis(2,3-dicarboxyphenoxy)diphenyl ether dianhydride; 4,4'-bis(2,3-dicarboxyphenoxy)diphenyl sulfone dianhydride; 4,
  • organic diamines examples include 1, 4-butane diamine, l,5-pentanediamine,
  • any regioisomer of the foregoing compounds can be used.
  • C alkylated or poly(Ci-4)alkylated derivatives of any of the foregoing can be used, for example a polymethylated 1,6- hexanediamine. Combinations of these compounds can also be used.
  • the organic diamine is m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, or a combination thereof.
  • the poly(etherimide)s 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 poly(etherimide) has a weight average molecular weight (Mw) of 1,000 to 150,000 grams/mole (Dalton), as measured by gel permeation chromatography, using polystyrene standards.
  • the poly(etherimide) has an Mw of 10,000 to 80,000 Daltons.
  • Such poly(etherimide)s typically have an intrinsic viscosity greater than 0.2 deciliters per gram (dl/g), or, more preferably, 0.35 to 0.7 dl/g as measured in m-cresol at 25°C.
  • the poly(etherimide)s have a glass transition temperature (Tg) of 220 to 320°C, preferably 240 to 320°C, more preferably 245 to 312°C, determined by differential scanning calorimetry (DSC) as per ASTM D3418 with a 20°C/min heating rate.
  • Tg glass transition temperature
  • DSC differential scanning calorimetry
  • Examples of poly(etherimide)s having such glass transition temperatures include poly(etherimide) sulfones as described herein.
  • the poly(etherimide)s can be present in an amount of 5 to 50 wt.%, 10 to 40 wt.%, or 15 to 25 wt.%, each based on the total weight of the thermoplastic compositions.
  • the thermoplastic composition optionally further includes additives known in the art for use in wire covering applications, provided that the additives do not substantially adversely affect the desired properties of the compositions.
  • additives include reinforcing fillers, UV absorbers, light stabilizers, heat stabilizers, lubricants, plasticizers, pigments, dyes, colorants, anti-static agents, foaming agents, blowing agents, metal deactivators, antioxidants, nucleating agents, and combinations comprising one or more of the foregoing additives.
  • thermoplastic compositions further comprise greater than zero to less than 8 wt% of an additive comprising a processing aid, a heat stabilizer, an antioxidant, an ultra violet light absorber, a flame retardant, an anti-drip agent, or a combination thereof, based on the total weight of the thermoplastic composition.
  • the thermoplastic compositions contain no additives.
  • 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, or a combination 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 embodiments, phosphoms containing stabilizers with a molecular weight greater than or equal to 500 are useful. Flow aids and mold release compounds are also contemplated. When present, the total amount of organic additive is 0 to 5 percent by weight, based on the combined weight of the polymer components.
  • a color concentrate or master batch can optionally be added to the composition prior to or during extrusion coating.
  • a color concentrate is typically present in an amount less than or equal to 3 weight percent, based on the total weight of the composition.
  • the master batch comprises a poly(etherimide-siloxane) copolymer.
  • the thermoplastic composition can be prepared by melt mixing or a combination of dry blending and melt mixing. Melt mixing can be performed in single or twin screw type extruders or similar mixing devices which can apply a shear and heat to the components. Melt mixing can be performed at temperatures greater than or equal to the melting temperatures of the copolymers and less than the degradation temperatures of either of the copolymers.
  • All of the ingredients can be added initially to the processing system.
  • the ingredients can be added sequentially and/or through the use of one or more master batches. It can be advantageous to apply a vacuum to the melt through one or more vent ports in the extruder to remove volatile impurities in the composition.
  • melt-mixing is performed using an extruder and the composition exits the extruder in a strand or multiple strands. The shape of the strand is dependent upon the shape of the die used and has no particular limitation.
  • the composition is the product of melt-mixing the polymers and, when present, any additives.
  • thermoplastic compositions can have a desirable combination of properties.
  • the thermoplastic compositions can have a heat deflection temperature of at least l60°C, for example 160 to l80°C as measured on a sample with a thickness of 3.2 mm at 1.82 MPa in accordance with ASTM D648.
  • thermoplastic compositions can have a flexural modulus of 800 to 4,000 MegaPascal (MPa), or 1,000 to 3,000 MPa, or 2,000 to 3,000 MPa as measured according to ASTM D790 at 1.27 m/min.
  • thermoplastic compositions can have a flexural strength at yield of greater than 50 to 150 MPa, determined in accordance with ASTM 790 at 1.27 m/min.
  • thermoplastic compositions can have a tensile stress at break of 30 to 100 MPa, or 50 to 90 MPa, as measured according to ASTM D638.
  • thermoplastic compositions can have an elongation to beak of 20 to 100%, or 40 to 100 %, as measured according to ASTM D638.
  • thermoplastic compositions can have a notched Izod impact strength of 50 to 100 J/m, as measured according to ASTM D 256 at a pendulum energy of 5 lbf/ft.
  • the thermoplastic composition can be injection molded and/or thermoformed to form an article.
  • the present composition now provides for a previously unmet need for a composition that has a ductility that is better than aromatic polyketones such as poly ary letherketones, that retains the advantageous processing features found in aromatic polyketones. Users can now make a variety of articles that exhibit performance properties that are valued by their respective customers, for example in subway, aircraft, and passenger vehicle applications.
  • thermoplastic compositions as disclosed herein have desirable properties for high-heat wire covering applications.
  • a coated wire comprises a conductor and a covering disposed over the electrically conductive wire.
  • the covering comprises the thermoplastic compositions as described herein.
  • thermoplastic compositions can be applied to the electrically conductive wire by a suitable method such as extrusion coating, injection molding, compression molding, or wire extrusion to form a coated wire.
  • a coating extruder equipped with a screw, crosshead, breaker plate, distributor, nipple, and die can be used.
  • the melted thermoplastic compositions form a covering disposed over a circumference of the electrically conductive wire.
  • Extrusion coating can employ a single taper die, a double taper die, other appropriate die or combination of dies to position the conductor centrally and avoid die lip build-up. Other coating methods that are generally known in the art can also be used.
  • thermoplastic compositions before they are applied to the electrically conductive wire.
  • Exemplary drying conditions are 60 to 160°C for 2 to 20 hours.
  • the thermoplastic compositions are melt filtered, prior to formation of the covering, through one or more filters.
  • the thermoplastic composition will have substantially no particles greater than 80 micrometers in size.
  • any particulates present will be less than or equal to 40 micrometers in size.
  • the presence and size of particulates can be determined using microscopy or light scattering techniques.
  • Substantially no particulates is defined as having less than or equal to 3 particulates, or, more preferably, less than or equal to 2 particulates, or, even more preferably, less than or equal to 1 particulate per one gram sample.
  • Low levels of particulates are beneficial for giving a layer of insulation on a coated wire that will not have electrically conductive defects as well as providing coverings with improved mechanical properties.
  • the extruder temperature during coating is generally less than the degradation temperature of the particular poly(arylene ether ketone), poly(arylene ether sulfone), and poly(etherimide) used. Additionally the processing temperature is adjusted to provide a sufficiently fluid molten composition to afford a covering for the conductor, for example, higher than the softening point of the thermoplastic composition, or more preferably at least 20°C higher than the melting point of the thermoplastic composition.
  • the conductive wire After coating the conductive wire is usually cooled using a water bath, water spray, air jets, or a combination comprising one or more of the foregoing cooling methods.
  • Exemplary water bath temperatures are 20 to 90°C, or 80 to 90°C.
  • thermoplastic compositions can be applied to the electrically conductive wire to form a covering disposed over and in physical contact with the electrically conductive wire.
  • additional layers can be applied to the covering. Any known methods known in the art can be used.
  • the covering formed from the thermoplastic compositions as described herein can be in direct physical contact with the electrically conductive wire.
  • the thermoplastic compositions can also be applied to an electrically conductive wire having one or more intervening layers between the electrically conductive wire and the covering to form a covering disposed over the electrically conductive wire.
  • an optional adhesion promoting layer can be disposed between the electrically conductive wire and covering.
  • the electrically conductive wire can be coated with a metal deactivator prior to applying the covering.
  • a metal deactivator can be mixed with the thermoplastic composition.
  • the intervening layer comprises a thermoplastic or thermoset composition that, in some cases, is foamed.
  • the electrically conductive wires can comprise a single strand or a plurality of strands. In some cases, a plurality of strands can be bundled, twisted, braided, or a combination of the foregoing to form a electrically conductive wire. Suitable materials for the electrically conductive wires include, but are not limited to, copper, aluminum, lead, gold, silver, iron, nickel, chromium, and alloys comprising at least one of the foregoing metals. In an exemplary embodiment, the electrically conductive wires comprise copper. The electrically conductive wires can also be coated with, e.g., tin, gold, or silver. In some embodiments the electrically conductive wires comprise optical fibers.
  • the cross-sectional area of the electrically conductive wires and thickness of the covering can vary and is typically determined by the desired application for the coated wires.
  • the covering can have a thickness of 0.01 to 10 millimeters (mm) or, more preferably, 0.05 to 5 mm, or, even more preferably 0.1 to 2 mm.
  • An electrical wire comprising a covering comprising the thermoplastic composition can further have a wire tensile elongation at break of greater than 50% or greater than 80% determined according to UL1581 after 24 hours at 23°C.
  • An electrical wire comprising a covering comprising the thermoplastic composition can have a wire tear strength of greater than 80 N/mm determined according to ISO 34-1 in the presence of a conductor wire.
  • the cable can comprise additional protective elements, structural elements, or a combination thereof.
  • An exemplary protective element is a jacket which surrounds the group of coated wires.
  • the jacket and the covering on the coated wires, singly or in combination, can comprise the thermoplastic compositions described herein.
  • a structural element is a typically non-conductive portion which provides additional stiffness, strength, shape retention capability or the like.
  • coated wires can be used as coated wires including, for example, for harness wire for automobiles, wire for household electrical appliances, wire for electric power, wire for instruments, wire for information communication, wire for electric cars, as well as ships, airplanes, and the like.
  • Specific applications that can benefit from coated electrical wires comprising the thermoplastic composition are those requiring high-heat, thin-walled wire coverings, for example for high-heat train, automobile, aircraft, and data transmission applications.
  • an article can comprise the electrical wire having a covering comprising the thermoplastic composition, wherein the article is a railway vehicle component, an automobile component, or an aircraft component.
  • an electrical wire includes an electrically conductive wire; and a covering disposed over the electrically conductive wire, wherein the covering comprises a thermoplastic composition that comprises, based on the total weight of the thermoplastic composition: 5 to 90 wt.%, preferably 35 to 55 wt.%, of a poly(ether ketone), poly(ether ether ketone), poly(ether ketone ketone), or a combination thereof, preferably a poly(ether ether ketone); 5 to 90 wt%, preferably 35 to 55 wt.%, of a poly(arylene ether sulfone), wherein the poly(arylene ether sulfone) comprises units of the formula
  • T is 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, and Z is 2,2-(4- phenylene)isopropylidene, and at least 10 mol% of R is bis(4,4’-phenylene)sulfone, bis(3,4’- phenylene)sulfone, bis(3,3’-phenylene)sulfone, or a combination thereof; and R is is m- phenylene, p-phenylene, or a diarylene sulfone, or a combination thereof, and the
  • poly(etherimide) has a glass transition temperature of 220°C to 320°C, determined by differential scanning calorimetry (DSC) as per ASTM D3418 with a 20°C/min heating rate.
  • the electrical wire of this aspect can include greater than zero to less than 8 wt% of an additive comprising a processing aid, a heat stabilizer, an antioxidant, an ultra violet light absorber, a flame retardant, an anti-drip agent, or a combination thereof, based on the total weight of the thermoplastic composition.
  • the electrical wire of this aspect can have all of the following properties: a tensile elongation at break of greater than 50%, preferably greater than 80%, determined according to UL-1581 after 24 hours at 23°C; or a tear strength of greater than 80 N/mm, determined according to ISO 34-1 in the presence of a conductor wire.
  • An intervening layer can be disposed between the electrically conductive wire and the covering.
  • the poly(etherimide) when the poly(etherimide) a glass transition temperature of 240 to 320°C, more preferably 245 to 3l2°C, determined by differential scanning calorimetry (DSC) as per ASTM D3418 with a 20°C/min heating rate; wherein the thermoplastic composition has all of the following properties: a heat deflection temperature of at least l60°C, as measured on a sample with a thickness of 3.2 mm at 1.82 MPa in accordance with ASTM D648; a flexural modulus of 2,000 to 3,000 MPa, determined in accordance with ASTM 790 at 1.27 m/min; or a flexural strength at yield of 50 to 150 MPa, determined in accordance with ASTM 790 at 1.27 m/min.
  • DSC differential scanning calorimetry
  • the wire coverings from the example pellets were made on a single screw extruder using a tube die.
  • the example pellets were dried at l50°C for 4 hours prior to extrusion.
  • the wire covering thickness was in the range of 0.4-0.5 millimeters (mm), and the coating was done on solid copper wire with a diameter of 1.5 mm.
  • the wire extrusion was carried out at 350-380°C and 20-50 m/min line speed.
  • DMA Dynamic mechanical analysis
  • compositions of the disclosure (Ex 2 and Ex 5), along with control or comparative composition (CExl), were tested for impact, flow, and heat performance. The formulations and the results are shown in Table 5.
  • compositions of the disclosure (Ex 2 - Ex 5) have excellent compatibility with no delamination visible to the naked eye. Compared to control, the compositions according to the disclosure have improved heat performance, preferably in HDT performance. Meanwhile the compositions of the disclosure have comparable mechanical properties as the control formulation.
  • the wire coverings were formed from the formulations of CEx 1, Ex 4, and Ex 5. The tensile measurements and tear strength test on wire samples was done and data is shown in
  • An electrical wire comprising: an electrically conductive wire; and a covering disposed over the electrically conductive wire, wherein the covering comprises a thermoplastic composition that comprises, based on the total weight of the thermoplastic composition: 5 to 90 wt.% of a poly(arylene ether ketone); 5 to 90 wt% of a poly(arylene ether sulfone); and 5 to 50 wt% of a poly(etherimide).
  • Aspect 2 The electrical wire of Aspect 1, wherein the poly(arylene ether ketone) comprises poly(ether ketone), poly(ether ether ketone), poly(ether ketone ketone), or a combination thereof, and preferably the poly(arylene ether ketone) comprises a poly(ether ether ketone).
  • Aspect 3 The electrical wire of Aspect 1 or Aspect 2, wherein the poly(arylene ether sulfone) is of the formula -[Ar 4 -S0 2 -Ar 5 -0] t -[Ar 6 -0] s -, wherein t is greater than 1, s is 0 or greater than one, and Ar 1 , Ar 2 , and Ar 3 are each independently a substituted or unsubstituted, monocyclic or polycyclic aromatic group having 6 to 30 carbons.
  • Aspect 4 The electrical wire of Aspect 3, wherein the poly(arylene ether sulfone) comprises units of the formula
  • Aspect 5 The electrical wire of any one or more of Aspects 1 to 4, wherein the poly(etherimide) comprises structural units of the formula:
  • Aspect 6 The electrical wire of any one or more of Aspects 1 to 5, wherein the poly(etherimide) has a glass transition temperature of 220°C to 320°C, determined by differential scanning calorimetry (DSC) as per ASTM D3418 with a 20°C/min heating rate.
  • DSC differential scanning calorimetry
  • Aspect 7 The electrical wire of any one or more of Aspects 5 to 6, wherein T is -O-Z-O-, wherein Z is 2,2-(4-phenylene)isopropylidene, and at least 10 mol% of R is bis(4,4’- phenylene)sulfone, bis(3, 4’ -phenylene) sulfone, bis(3, 3’-phenylene) sulfone, or a combination thereof.
  • Aspect 8 The electrical wire of any one or more of Aspects 1 to 7, wherein the thermoplastic composition comprises, based on the total weight of the thermoplastic
  • composition 35 to 55 wt.% of the poly(arylene ether ketone); 35 to 55 wt% of the poly(arylene ether sulfone); and 15 to 25 wt% of the poly(etherimide).
  • thermoplastic composition further comprises greater than zero to less than 8 wt% of an additive comprising a processing aid, a heat stabilizer, an antioxidant, an ultra violet light absorber, a flame retardant, an anti-drip agent, or a combination thereof, based on the total weight of the thermoplastic composition.
  • an additive comprising a processing aid, a heat stabilizer, an antioxidant, an ultra violet light absorber, a flame retardant, an anti-drip agent, or a combination thereof, based on the total weight of the thermoplastic composition.
  • Aspect 10 The electrical wire of any one or more of Aspects 1 to 9, wherein the covering has one or more of the following properties a tensile elongation at break of greater than 50%, preferably greater than 80%, determined according to UL-1581 after 24 hours at 23°C; or a tear strength of greater than 80 N/mm, determined according to ISO 34-1 in the presence of a conductor wire.
  • Aspect 11 The electrical wire of any one or more of Aspects 1 to 10, wherein the covering has a thickness of 0.01 to 10 millimeters, preferably 0.1 to 2 millimeters.
  • Aspect 12 The electrical wire of any one or more of Aspects 1 to 11, wherein the electrically conductive wire comprises copper, aluminum, lead, gold, silver, iron, nickel, chromium, and alloys comprising at least one of the foregoing.
  • Aspect 13 The electrical wire of any one or more of Aspects 1 to 12, wherein the electrical wire further comprises an intervening layer between the electrically conductive wire and the covering.
  • Aspect 14 An article comprising the electrical wire of any one or more of Aspects 1 to 13.
  • Aspect 15 The article of Aspect 14, wherein the article is a construction component, a building component, an electrical device component, a railway vehicle component, an automobile component, a marine vehicle component, an aircraft component, or a data transmission component.
  • thermoplastic composition comprising, based on the total weight of the thermoplastic composition: 5 to 90 wt.% of a poly(arylene ether ketone); 5 to 90 wt.% of a poly(arylene ether sulfone); and 5 to 50 wt.% of a poly(etherimide) having a glass transition temperature of 220 to 320°C, preferably 240 to 320°C, more preferably 245 to 3l2°C, determined by differential scanning calorimetry (DSC) as per ASTM D3418 with a 20°C/min heating rate; wherein the thermoplastic composition has one or more of the following properties: a heat deflection temperature of at least l60°C, as measured on a sample with a thickness of 3.2 mm at 1.82 MPa in accordance with ASTM D648; a flexural modulus of 2,000 to 3,000 MPa, determined in accordance with ASTM 790 at 1.27 m/min; or a flexural
  • Aspect 17 The thermoplastic composition of Aspect 16, wherein the
  • poly(arylene ether ketone) comprises poly(ether ketone), poly(ether ether ketone), poly(ether ketone ketone), or a combination thereof, preferably the aromatic polyketone comprises poly (ether ether ketone).
  • Aspect 18 The thermoplastic composition of Aspect 16 or 17, wherein the poly(arylene ether sulfone) is a polyethersulfone, a polyphenylene sulfone, a
  • polyetherethersulfone a polysulfone, or a combination thereof.
  • Aspect 19 The thermoplastic composition of any one or more of Aspects 16 to 18, wherein the poly(etherimide) comprises structural units of the formula: wherein at least 10 mol% of R is bis(4,4’-phenylene)sulfone, bis(3,4’-phenylene)sulfone, bis(3,3’-phenylene)sulfone, or a combination thereof; 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, and Z is an aromatic CV24 monocyclic or polycyclic moiety optionally substituted with 1 to 6 Ci- 8 alkyl groups, 1 to 8 halogen atoms, or a combination thereof, preferably Z is 2,2-(4- phenylene)isopropylidene.
  • thermoplastic composition of any one or more of Aspects 16 to 19, wherein the thermoplastic composition comprises, based on the total weight of the thermoplastic composition: 35 to 55 wt.% of the poly(arylene ether ketone); 35 to 55 wt% of the poly(arylene ether sulfone); and 15 to 25 wt% of the poly(etherimide).
  • 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 (-(CH 2 )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.“Alkylarylene” means an arylene group substituted with an alkyl group.“Arylalkylene” means an alkylene 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.
  • any reference to standards, regulations, testing methods and the like refers to the standard, regulation, guidance, or method that is in force as of January 1, 2018.

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Abstract

Fil électrique qui comprend : un fil électroconducteur ; et un revêtement disposé sur le fil électroconducteur, le revêtement comprenant une composition thermoplastique qui comprend, sur la base du poids total de la composition thermoplastique : 5 à 90 % en poids d'une poly(arylène éther cétone) ; 5 à 90 % en poids d'une poly(arylène éther sulfone) ; et 5 à 50 % en poids d'un poly(étherimide).
PCT/IB2019/057349 2018-09-19 2019-08-30 Revêtement pour fil électrique comprenant une composition thermoplastique WO2020058790A1 (fr)

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WO2020205428A1 (fr) 2019-03-29 2020-10-08 Essex Group Llc Fil de bobinage à isolant thermoplastique
WO2021067168A1 (fr) 2019-10-02 2021-04-08 Essex Group Llc Films isolants polymères
WO2021219889A1 (fr) * 2020-04-30 2021-11-04 Arkema France Conducteur isolé apte à être utilisé dans un bobinage, bobinage en dérivant et procédés de fabrication correspondants
EP4219595A4 (fr) * 2020-09-23 2024-03-13 Mitsubishi Gas Chemical Co Composition de résine de polyimide et corps moulé

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Cited By (8)

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Publication number Priority date Publication date Assignee Title
WO2020205428A1 (fr) 2019-03-29 2020-10-08 Essex Group Llc Fil de bobinage à isolant thermoplastique
EP3948900A4 (fr) * 2019-03-29 2022-11-02 Essex Furukawa Magnet Wire Usa Llc Fil de bobinage à isolant thermoplastique
US11615914B2 (en) 2019-03-29 2023-03-28 Essex Furukawa Magnet Wire Usa Llc Magnet wire with thermoplastic insulation
WO2021067168A1 (fr) 2019-10-02 2021-04-08 Essex Group Llc Films isolants polymères
EP4037904A4 (fr) * 2019-10-02 2023-11-01 Essex Furukawa Magnet Wire Usa Llc Films isolants polymères
WO2021219889A1 (fr) * 2020-04-30 2021-11-04 Arkema France Conducteur isolé apte à être utilisé dans un bobinage, bobinage en dérivant et procédés de fabrication correspondants
FR3109848A1 (fr) * 2020-04-30 2021-11-05 Arkema France Conducteur isolé apte à être utilisé dans un bobinage, bobinage en dérivant et procédés de fabrication correspondants.
EP4219595A4 (fr) * 2020-09-23 2024-03-13 Mitsubishi Gas Chemical Co Composition de résine de polyimide et corps moulé

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