WO2010030478A2 - Composition de poly(arylène éther), procédé, et article selon l'invention - Google Patents

Composition de poly(arylène éther), procédé, et article selon l'invention Download PDF

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WO2010030478A2
WO2010030478A2 PCT/US2009/054388 US2009054388W WO2010030478A2 WO 2010030478 A2 WO2010030478 A2 WO 2010030478A2 US 2009054388 W US2009054388 W US 2009054388W WO 2010030478 A2 WO2010030478 A2 WO 2010030478A2
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weight percent
poly
ultraviolet radiation
composition
polystyrene
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WO2010030478A3 (fr
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Sean W. Culligan
Hua Guo
Steven Raymond Klei
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Sabic Innovative Plastics Ip B.V.
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    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
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    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
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    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
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    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C08L23/0807—Copolymers of ethene with unsaturated hydrocarbons only containing more than three carbon atoms
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    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
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    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/005—Modified block copolymers
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    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
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    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
    • C08L53/025—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes modified
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    • 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
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
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    • C08J2423/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
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    • C08J2423/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2423/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2423/16—Ethene-propene or ethene-propene-diene copolymers
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    • C08J2453/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
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    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers

Definitions

  • Poly(arylene ether) is a type of plastic known for its excellent water resistance, dimensional stability, and inherent flame retardancy. Properties such as strength, stiffness, chemical resistance, and heat resistance can be tailored by blending it with various other plastics in order to meet the requirements of a wide variety of consumer products, for example, plumbing fixtures, electrical boxes, automotive parts, and insulation for wire and cable.
  • Poly( vinyl chloride) is currently the commercially dominant material for flame retardant wire and cable insulation.
  • poly( vinyl chloride) is a halogenated material.
  • white-colored small appliances and personal electronic devices there is also a particular need for white or off-white colored cable insulation compositions that retain their color after photochemical aging.
  • halogen-free poly(arylene ether) compositions can possess the physical and flame retardant properties needed for use as wire and cable insulation. See, for example, U.S. Patent Application Publication Nos. US 2006/131050 Al and US 2006/131052 Al and US 2006/135661 Al of Mhetar et al., US 2006/131053 Al and US 2006/134416 Al of Kubo et al., US 2006/131059 Al of Xu et al., and US 2006/135695 Al of Guo et al.
  • the compositions disclosed in these references are difficult to formulate in a white or off-white color, or they exhibit insufficient thermal or photochemical color stability, or both.
  • thermoplastic composition comprising: melt-kneading 20 to 40 weight percent of a poly(arylene ether), 10 to 60 weight percent of a thermoplastic elastomer, 5 to 25 weight percent of a flame retardant, and 0.4 to 10 weight percent of an ultraviolet radiation stabilizer composition comprising at least two ultraviolet stabilizing compounds selected from different subgroups of the group consisting of a first subgroup consisting of ultraviolet radiation absorbers, a second subgroup consisting of hindered amine light stabilizers, and a third subgroup consisting of cycloaliphatic epoxy compounds to form a thermoplastic composition; wherein all weight percents are based on the total weight of the composition; wherein the ultraviolet radiation stabilizer composition is provided in the form of an ultraviolet radiation stabilizer masterbatch comprising the ultraviolet radiation stabilizer composition and the thermoplastic elastomer; and wherein the thermoplastic composition comprises less than or equal to 20 weight percent of rubber-modified poly
  • thermoplastic composition prepared by the above method, wherein the poly(arylene ether) comprises a poly(2,6-dimethyl-l,4-phenylene ether) having an intrinsic viscosity of 0.35 to 0.6 deciliter per gram measured at 25°C in chloroform; wherein the thermoplastic composition comprises 20 to 30 weight percent of the poly(arylene ether); wherein the thermoplastic elastomer comprises a polystyrene-poly(ethylene-butylene)- polystyrene triblock copolymer, a polystyrene-poly(ethylene-butylene-styrene) -polystyrene triblock copolymer, and a random copolymer of ethylene and propylene; wherein the thermoplastic composition comprises 25 to 35 weight percent of the thermoplastic elastomer; wherein the flame retardant comprises melamine polyphosphate and magnesium hydroxide; wherein the thermoplastic composition comprises 13 to 20 weight percent of the flame retard
  • an ultraviolet radiation stabilizer masterbatch comprising: 80 to 99 weight percent of a thermoplastic elastomer selected from the group consisting of hydrogenated block copolymers of an alkenyl aromatic compound and a conjugated diene, polyolefin block copolymers having a polyethylene or polypropylene block and block that is a copolymer of ethylene and a C 3 -C 12 olefin, random copolymers of ethylene and a C 3 -C 12 alpha-olefin, and mixtures thereof, and 1 to 20 weight percent of an ultraviolet radiation stabilizer composition comprising at least two ultraviolet stabilizing compounds selected from different subgroups of the group consisting of a first subgroup consisting of ultraviolet radiation absorbers, a second subgroup consisting of hindered amine light stabilizers, and a third subgroup consisting of cycloaliphatic epoxy compounds; wherein all weight percents are based on the total weight of the ultraviolet radiation stabilizer masterbatch.
  • a thermoplastic elastomer selected
  • thermoplastic elastomer resins In their course of their research on light-colored thermoplastic compositions, the present inventors were aware of the photochemical yellowing challenge inherent in poly(arylene ether)s. They therefore initially expected that blends of poly(arylene ether)s and thermoplastic elastomer resins would benefit from compounding methods in which ultraviolet radiation stabilizers are preferentially distributed into the poly(arylene ether) -containing phase. However, it was unexpectedly discovered that improved photostability of the blends was obtained when ultraviolet radiation stabilizers were pre-compounded with the thermoplastic elastomer component.
  • the resulting blends show improved photostability (reduced photochemical yellowing) compared to blends in which all components are melt blended simultaneously, as well as blends in which the ultraviolet radiation stabilizers were pre-compounded with the poly(arylene ether) component.
  • one embodiment is a method of forming a thermoplastic composition, comprising: melt-kneading 20 to 40 weight percent of a poly(arylene ether), 10 to 60 weight percent of a thermoplastic elastomer, 5 to 25 weight percent of a flame retardant, and 0.4 to 10 weight percent of an ultraviolet radiation stabilizer composition comprising at least two ultraviolet stabilizing compounds selected from different subgroups of the group consisting of a first subgroup consisting of ultraviolet radiation absorbers, a second subgroup consisting of hindered amine light stabilizers, and a third subgroup consisting of cycloaliphatic epoxy compounds to form a thermoplastic composition; wherein all weight percents are based on the total weight of the composition; wherein the ultraviolet radiation stabilizer composition is provided in the form of an ultraviolet radiation stabilizer masterbatch comprising the ultraviolet radiation stabilizer composition and the thermoplastic elastomer; and wherein the thermoplastic composition comprises less than or equal to 20 weight percent of rubber- modified polystyrene.
  • the first component present in the melt-kneaded mixture is the poly(arylene ether).
  • the poly(arylene ether) comprises repeating structural units having the formula
  • each Z 1 is independently halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio (that is, (Ci-Ci 2 hydrocarbyl)S-), Ci-Ci 2 hydrocarbyloxy, or C 2 -Ci 2 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; and each Z is independently hydrogen, halogen, unsubstituted or substituted Ci-Ci 2 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, Ci-Ci 2 hydrocarbylthio, Ci-Ci 2 hydrocarbyloxy, or C 2 -Ci 2 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms.
  • hydrocarbyl refers to a residue that contains only carbon and hydrogen.
  • the residue can be aliphatic or aromatic, straight-chain, cyclic, bicyclic, branched, saturated, or unsaturated. It can also contain combinations of aliphatic, aromatic, straight chain, cyclic, bicyclic, branched, saturated, and unsaturated hydrocarbon moieties.
  • the poly(arylene ether) comprises 2,6-dimethyl-l,4- phenylene ether units, 2,3,6-trimethyl-l,4-phenylene ether units, or a combination thereof.
  • the poly(arylene ether) can comprise molecules having aminoalkyl-containing end group(s), typically located in a position ortho to the hydroxy group. Also frequently present are tetramethyldiphenoquinone (TMDQ) end groups, typically obtained from 2,6- dimethylphenol-containing reaction mixtures in which tetramethyldiphenoquinone by-product is present.
  • TMDQ tetramethyldiphenoquinone
  • the poly(arylene ether) can be in the form of a homopolymer, a copolymer, a graft copolymer, an ionomer, or a block copolymer, as well as combinations comprising at least one of the foregoing.
  • the poly(arylene ether) can have a number average molecular weight of 3,000 to 40,000 atomic mass units (AMU) and a weight average molecular weight of 5,000 to 80,000 AMU, as determined by gel permeation chromatography using monodisperse polystyrene standards, a styrene divinyl benzene gel at 40°C and samples having a concentration of 1 milligram per milliliter of chloroform.
  • AMU atomic mass units
  • the poly(arylene ether) can have an intrinsic viscosity of 0.05 to 1.0 deciliter per gram (dL/g), as measured in chloroform at 25 0 C, specifically 0.1 to 0.8 dL/g, more specifically 0.2 to 0.6 dL/g, even more specifically 0.3 to 0.6 dL/g.
  • intrinsic viscosity of a poly(arylene ether) can increase by up to 30% on melt kneading.
  • the above intrinsic viscosity range of 0.05 to 1.0 deciliter per gram is intended to encompass intrinsic viscosities both before and after melt kneading to form the composition.
  • a blend of poly(arylene ether)s having different intrinsic viscosities can be used.
  • the poly(arylene ether) molecular weight distribution is characterized by a weight average molecular weight and a peak molecular weight, and the ratio of the weight average molecular weight to the peak molecular weight is about 1.3 : 1 to about 4 : 1, specifically 1.5:1 to about 3:1, more specifically 1.8:1 to about 2.5:1.
  • peak molecular weight is defined as the most commonly occurring molecular weight in the molecular weight distribution. In statistical terms, the peak molecular weight is the mode of the molecular weight distribution.
  • the peak molecular weight is the poly(arylene ether) molecular weight of the highest point in a plot of molecular weight on the x-axis versus absorbance on the y-axis.
  • the poly(arylene ether) molecular weight distribution is at least bimodal.
  • bimodal means that a plot of molecular weight on the x-axis versus frequency on the y-axis has two local maxima.
  • at least bimodal means that the plot has two or more local maxima.
  • the molecular weight distribution comprises a first local maximum having a first molecular weight (corresponding to M p ) and a second local maximum having a second molecular weight that is greater than the first molecular weight, and the ratio of the second molecular weight to the first molecular weight is about 2 : 1 to about 4 : 1.
  • the thermoplastic composition comprises 20 to 40 weight percent of the poly(arylene ether), based on the total weight of the composition. Within this range, the poly(arylene ether) amount specifically can be 22 to 30 weight percent, more specifically 24 to 28 weight percent.
  • the melt-kneaded mixture comprises a thermoplastic elastomer.
  • thermoplastic elastomer refers to an elastomeric copolymer comprising repeating units derived from ethylene and/or a C 3 -C 12 alpha-olefin.
  • Suitable thermoplastic elastomers include hydrogenated block copolymers of an alkenyl aromatic compound and a conjugated diene, polyolefin block copolymers having a (hard) polyethylene or polypropylene block and (soft) block that is a copolymer of ethylene and a C3-C12 olefin, random copolymers of ethylene and a C3-C12 alpha-olefin, and mixtures thereof.
  • the thermoplastic elastomer can comprise a hydrogenated block copolymer of an alkenyl aromatic compound and a conjugated diene.
  • this component is referred to herein as the "hydrogenated block copolymer".
  • the hydrogenated block copolymer may comprise 10 to 90 weight percent of poly( alkenyl aromatic) content and 90 to 10 weight percent of hydrogenated poly(conjugated diene) content.
  • the poly( alkenyl aromatic) content is 10 to 45 weight percent, specifically 20 to 40 weight percent.
  • the poly(alkenyl aromatic) content is greater than 45 weight percent to 90 weight percent, specifically 55 to 80 weight percent.
  • the hydrogenated block copolymer can have a weight average molecular weight of 40,000 to 400,000 atomic mass units.
  • the number average molecular weight and the weight average molecular weight may be determined by gel permeation chromatography and based on comparison to polystyrene standards.
  • the hydrogenated block copolymer has a weight average molecular weight of 200,000 to 400,000 atomic mass units, specifically 220,000 to 350,000 atomic mass units.
  • the hydrogenated block copolymer can have a weight average molecular weight of 40,000 to less than 200,000 atomic mass units, specifically 40,000 to 180,000 atomic mass units, more specifically 40,000 to 150,000 atomic mass units.
  • the alkenyl aromatic monomer used to prepare the hydrogenated block copolymer can have the structure
  • R 1 and R 2 each independently represent a hydrogen atom, a C 1 -C 8 alkyl group, or a C 2 -Cs alkenyl group
  • R 3 and R 7 each independently represent a hydrogen atom, a Ci-Cs alkyl group, a chlorine atom, or a bromine atom
  • R 4 , R 5 , and R 6 each independently represent a hydrogen atom, a Ci-Cs alkyl group, or a C 2 -Cs alkenyl group, or R 4 and R 5 are taken together with the central aromatic ring to form a naphthyl group, or R 5 and R 6 are taken together with the central aromatic ring to form a naphthyl group.
  • alkenyl aromatic monomers include, for example, styrene, chlorostyrenes such as p-chlorostyrene, and methylstyrenes such as alpha-methylstyrene and p-methylstyrene.
  • the alkenyl aromatic monomer is styrene.
  • the conjugated diene used to prepare the hydrogenated block copolymer can be a C 4 -C 20 conjugated diene.
  • Suitable conjugated dienes include, for example, 1,3-butadiene, 2-methyl-l,3-butadiene, 2-chloro-l,3-butadiene, 2,3-dimethyl-l,3-butadiene, 1,3-pentadiene, 1,3-hexadiene, and the like, and combinations thereof.
  • the conjugated diene is 1,3-butadiene, 2-methyl- 1,3-butadiene, or a combination thereof.
  • the conjugated diene consists of 1,3-butadiene.
  • the hydrogenated block copolymer is a copolymer comprising (A) at least one block derived from an alkenyl aromatic compound and (B) at least one block derived from a conjugated diene, in which the aliphatic unsaturated group content in the block (B) is at least partially reduced by hydrogenation. In some embodiments, the aliphatic unsaturation in the (B) block is reduced by at least 50 percent, specifically at least 70 percent.
  • the arrangement of blocks (A) and (B) includes a linear structure, a grafted structure, and a radial teleblock structure with or without a branched chain. Linear block copolymers include tapered linear structures and non-tapered linear structures.
  • the hydrogenated block copolymer has a tapered linear structure. In some embodiments, the hydrogenated block copolymer has a non-tapered linear structure. In some embodiments, the hydrogenated block copolymer comprises a B block that comprises random incorporation of alkenyl aromatic monomer.
  • Linear block copolymer structures include diblock (A-B block), triblock (A-B-A block or B-A-B block), tetrablock (A-B-A-B block), and pentablock (A-B-A-B-A block or B- A-B-A-B block) structures as well as linear structures containing 6 or more blocks in total of A and B, wherein the molecular weight of each A block may be the same as or different from that of other A blocks, and the molecular weight of each B block may be the same as or different from that of other B blocks.
  • the hydrogenated block copolymer is a diblock copolymer, a triblock copolymer, or a combination thereof.
  • the hydrogenated block copolymer is a polystyrene- poly(ethylene-butylene)-polystyrene triblock copolymer. In some embodiments, the hydrogenated block copolymer is a polystyrene-poly(ethylene-propylene) diblock copolymer. These block copolymers do not include the residue of any functionalizing agents or any monomers other than those indicated by their names.
  • the hydrogenated block copolymer excludes the residue of monomers other than the alkenyl aromatic compound and the conjugated diene. In some embodiments, the hydrogenated block copolymer consists of blocks derived from the alkenyl aromatic compound and the conjugated diene. It does not comprise grafts formed from these or any other monomers. It also consists of carbon and hydrogen atoms and therefore excludes heteroatoms.
  • the hydrogenated block copolymer includes the residue of one or more acid functionalizing agents, such as maleic anhydride.
  • thermoplastic elastomer comprises a polystyrene- poly(ethylene-propylene) diblock copolymer.
  • thermoplastic elastomer comprises a polystyrene- poly(ethylene-butylene)-polystyrene triblock copolymer.
  • the thermoplastic elastomer comprises a polystyrene- poly(ethylene-butylene-styrene) -polystyrene triblock copolymer.
  • hydrogenated block copolymers are known in the art and many hydrogenated block copolymers are commercially available.
  • Illustrative commercially available hydrogenated block copolymers include the polystyrene- poly(ethylene-propylene) diblock copolymers available from Kraton Polymers as KRATON G1701 and G1702; the polystyrene-poly(ethylene-butylene)-polystyrene triblock copolymers available from Kraton Polymers as KRATON G1641, G1650, G1651, G1654, G1657, G1726, G4609, G4610, GRP-6598, RP-6924, MD-6932M, MD-6933, and MD-6939; the polystyrene- poly(ethylene-butylene-styrene) -polystyrene (S-EB/S-S) triblock copolymers available from Kraton Polymers as KRATON RP-6935 and
  • the thermoplastic elastomer can comprise a polyolefin block copolymer comprising a (hard) polyethylene or polypropylene block and (soft) block that is a copolymer of ethylene and a C 3 -C 12 olefin.
  • a polyolefin block copolymer comprising a (hard) polyethylene or polypropylene block and (soft) block that is a copolymer of ethylene and a C 3 -C 12 olefin.
  • Such block copolymers and methods for their preparation are known in the art.
  • polyolefin block copolymers include those sold by Dow under the INFUSE trade name, those sold by Advanced Elastomer Systems under the VISTAFLEX trade name, those sold by Ferro Corporation under the FERROFLEX trade name, those sold by Republic Plastics under the ETA and RTA trade names, those sold by LyondellBasell Advanced Polyolefins under the DEXFLEX trade name, those sold by A. Schulman under the POLYTROPE trade name, those sold by Teknor Apex under the TELCAR trade name, those sold by DSM under the KELBUROU trade name, those sold by British Vita under the VITACOM TPO trade name, and those sold by SABIC under the VESTOLEN trade name.
  • the thermoplastic elastomer can comprise a random copolymer of ethylene and a C3-C12 alpha-olefin.
  • the C3-C12 alpha-olefin can be, for example, propylene, 1-butene, or 1-octene.
  • the thermoplastic elastomer comprises a random copolymer of ethylene and propylene.
  • the thermoplastic elastomer can comprise a mixture of the above-described elastomers.
  • the thermoplastic elastomer can comprise a polystyrene- poly(ethylene-butylene) -polystyrene triblock copolymer and a random copolymer of ethylene and propylene.
  • the thermoplastic elastomer can also comprise a polystyrene-poly(ethylene- butylene) -polystyrene triblock copolymer, a polystyrene-poly(ethylene-butylene-styrene)- polystyrene triblock copolymer, and a random copolymer of ethylene and propylene.
  • the thermoplastic composition comprises the thermoplastic elastomer in an amount of 10 to 60 weight percent, based on the total weight of the composition. Within this range, the thermoplastic elastomer amount can be specifically 20 to 45 weight percent, more specifically 25 to 35 weight percent.
  • the melt-kneaded composition comprises a flame retardant.
  • the flame retardant is a chemical compound or mixture of chemical compounds capable of improving the flame retardancy of the thermoplastic composition. Suitable flame retardants include organophosphate esters, metal dialkyl phosphinates, nitrogen-containing flame retardants, metal hydroxides, and mixtures thereof.
  • the flame retardant comprises an organophosphate ester.
  • organophosphate ester flame retardants include, but are not limited to, phosphate esters comprising phenyl groups, substituted phenyl groups, or a combination of phenyl groups and substituted phenyl groups, bis-aryl phosphate esters based upon resorcinol such as, for example, resorcinol bis(diphenyl phosphate), as well as those based upon bisphenols such as, for example, bisphenol A bis(diphenyl phosphate).
  • the organophosphate ester is selected from tris(alkylphenyl) phosphates (for example, CAS Reg. No.
  • resorcinol bis(diphenyl phosphate) (CAS Reg. No. 57583-54-7), bisphenol A bis(diphenyl phosphate) (CAS Reg. No. 181028-79-5), triphenyl phosphate (CAS Reg. No. 115-86-6), tris(isopropylphenyl) phosphates (for example, CAS Reg. No. 68937-41-7), and mixtures of two or more of the foregoing organophosphate esters.
  • the organophosphate ester comprises a bis-aryl phosphate having the formula
  • R is independently at each occurrence a C 1 -C 12 alkylene group; R 12 and R 13 are independently at each occurrence a C 1 -C 5 alkyl group; R 8 , R 9 , and R 11 are independently a C 1 - C 12 hydrocarbyl group; R 10 is independently at each occurrence a C 1 -C 12 hydrocarbyl group; n is 1 to 25; and si and s2 are independently an integer equal to 0, 1, or 2.
  • OR 8 , OR 9 , OR 10 and OR 11 are independently derived from phenol, a monoalkylphenol, a dialkylphenol or a trialkylphenol.
  • the bis-aryl phosphate is derived from a bisphenol.
  • exemplary bisphenols include 2,2-bis(4-hydroxyphenyl)propane (so-called bisphenol A), 2,2-bis(4-hydroxy-3-methylphenyl)propane, bis(4- hydroxyphenyl)methane, bis(4-hydroxy-3,5-dimethylphenyl)methane and l,l-bis(4- hydroxyphenyl)ethane.
  • the bisphenol comprises bisphenol A.
  • the flame retardant comprises a metal dialkyl phosphinate.
  • metal dialkyl phosphinate refers to a salt comprising at least one metal cation and at least one dialkyl phosphinate anion.
  • the metal dialkyl phosphinate has the formula
  • R , 14 and R , 15 are each independently Ci-C 6 alkyl; M is calcium, magnesium, aluminum, or zinc; and d is 2 or 3.
  • R 14 and R , 15 include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, and phenyl.
  • R 14 and R 15 are ethyl
  • M is aluminum
  • d is 3 (that is, the metal dialkyl phosphinate is aluminum tris(diethyl phosphinate)).
  • the metal dialkyl phosphinate is in particulate form.
  • the metal dialkyl phosphinate particles may have a median particle diameter (D50) less than or equal to 40 micrometers, or, more specifically, a D50 less than or equal to 30 micrometers, or, even more specifically, a D50 less than or equal to 25 micrometers.
  • the metal dialkyl phosphinate may be combined with a polymer, such as a poly(arylene ether), a polyolefin, a polyamide, a block copolymer, or combination thereof, to form a masterbatch.
  • the metal dialkyl phosphinate masterbatch comprises the metal dialkyl phosphinate in an amount greater than is present in the thermoplastic composition.
  • Employing a masterbatch for the addition of the metal dialkyl phosphinate to the other components of the thermoplastic composition can facilitate addition and improve distribution of the metal dialkyl phosphinate.
  • the flame retardant comprises a nitrogen-containing flame retardant comprising a nitrogen-containing heterocyclic base and a phosphate or pyrophosphate or polyphosphate acid.
  • the nitrogen-containing flame retardant has the formula
  • g is 1 to 10,000, and the ratio of f to g is 0.5:1 to 1.7:1, specifically 0.7:1 to 1.3:1, more specifically 0.9:1 to 1.1:1. It will be understood that this formula includes species in which one or more protons are transferred from the phosphate group(s) to the melamine group(s).
  • the nitrogen-containing flame retardant is melamine phosphate (CAS Reg. No. 20208-95-1).
  • the nitrogen-containing flame retardant is melamine pyrophosphate (CAS Reg. No. 15541 60-3).
  • g is, on average, greater than 2
  • the nitrogen-containing flame retardant is a melamine polyphosphate (CAS Reg. No. 56386-64- T).
  • the nitrogen-containing flame retardant is melamine pyrophosphate, melamine polyphosphate, or a mixture thereof.
  • g has an average value of greater than 2 to 10,000, specifically 5 to 1,000, more specifically 10 to 500.
  • g has an average value of greater than 2 to 500.
  • Methods for preparing melamine phosphate, melamine pyrophosphate, and melamine polyphosphate are known in the art, and all are commercially available.
  • melamine polyphosphates may be prepared by reacting polyphosphoric acid and melamine, as described, for example, in U.S.
  • the nitrogen-containing flame retardant can have a low volatility.
  • the nitrogen-containing flame retardant exhibits less than 1 percent weight loss by thermogravimetric analysis when heated at a rate of 20 0 C per minute from 25 to 280 0 C, specifically 25 to 300 0 C, more specifically 25 to 320 0 C.
  • the flame retardant comprises a metal hydroxide.
  • Suitable metal hydroxides include all those capable of providing fire retardancy, as well as combinations of such metal hydroxides.
  • the metal hydroxide can be chosen to have substantially no decomposition during processing of the fire additive composition and/or flame retardant thermoplastic composition. Substantially no decomposition is defined herein as amounts of decomposition that do not prevent the flame retardant additive composition from providing the desired level of fire retardancy.
  • Exemplary metal hydroxides include, but are not limited to, magnesium hydroxide (for example, CAS Reg. No. 1309-42-8), aluminum hydroxide (for example, CAS Reg. No. 21645-51-2), cobalt hydroxide (for example, CAS Reg. No.
  • the metal hydroxide comprises magnesium hydroxide.
  • the metal hydroxide has an average particle size less than or equal to 10 micrometers and/or a purity greater than or equal to 90 weight percent.
  • the metal hydroxide can be coated, for example, with stearic acid or other fatty acid.
  • the flame retardant comprises melamine polyphosphate and magnesium hydroxide.
  • the flame retardant is present in the thermoplastic composition in an amount of 5 to 25 weight percent of a flame retardant, based on the total weight of the thermoplastic composition. Within this range, the flame retardant amount can be 10 to 20 weight percent, specifically 14 to 18 weight percent. When the flame retardant comprises two or more components, these components can be used an any amount, provided that the total amount of flame retardant is in the range of 5 to 25 weight percent.
  • the thermoplastic composition comprises an ultraviolet radiation stabilizer composition.
  • the ultraviolet radiation stabilizer composition comprises at least two ultraviolet stabilizing compounds selected from different subgroups of the group consisting of a first subgroup consisting of ultraviolet radiation absorbers, a second subgroup consisting of hindered amine light stabilizers, and a third subgroup consisting of cycloaliphatic epoxy compounds.
  • Classes of ultraviolet radiation absorbers include benzophenones, benzotriazoles, triazines, oxanilides, and cyanoacrylates.
  • Benzophenone ultraviolet radiation absorbers include those having the structure
  • R 16 , R 17 , and R 18 are each independently hydrogen or C 1 -C 12 alkyl.
  • Illustrative benzophenone ultraviolet radiation absorbers include benzoresorcinol (CAS Reg. No. 131-56- 6; UVINUL 400 from BASF), oxybenzone (CAS Reg. No. 131-57-7; CYASORB UV-9 from Cytec), and octabenzone (CAS Reg. No. 1843-05-6; CYASORB UV-531 from Cytec).
  • Benzotriazole ultraviolet radiation absorbers include those having the structure
  • X 1 is hydrogen or chloro
  • R 19 is C 1 -C 12 alkyl
  • R 20 is hydrogen or C 1 -C 12 alkyl.
  • Illustrative benzotriazole ultraviolet radiation absorbers include 2-(2'-hydroxy-5'-tert- octylphenyl)benzotriazole (CAS Reg. No. 3147-75-9; CYASORB 5411 from Cytec), 2-(2'- hydroxy-3',5'-di-tert-butylphenyl)benzotriazole (CAS Reg. No.
  • TINUVIN 320 from Ciba Specialty Chemicals
  • 2-(2'-hydroxy-3',5'-di-tert-pentylphenyl)benzotriazole CAS Reg. No. 25973-55-1
  • TINUVIN 328 from Ciba Specialty Chemicals
  • Triazine ultraviolet radiation absorbers include those having the structure
  • Ar 1 and Ar 2 are each independently an optionally substituted C 6 -Ci S aryl group, and R 21 is hydrogen or a C 1 -C 12 hydrocarbyl group.
  • Illustrative triazine ultraviolet radiation absorbers include 2-[4,6-bis(2,4-dimethylphenyl)-l,3,5-triazin-2-yl]-5-(octyloxy)phenol (CAS Reg. No. 2725-22-6; CYASORB UV-1164 from Cytec), and 2-[4,6-dilphenyl-l,3,5- triazin-2-yl]-5-(hexyloxy)phenol (CAS Reg. No. 147315-50-2); TINUVIN 1577 from Ciba Specialty Chemicals).
  • Oxanilide ultraviolet radiation absorbers include those having the structure
  • Ar 3 and Ar 4 are each independently an optionally substituted C 6 -Ci S aryl group.
  • Illustrative oxanilide ultraviolet radiation absorbers include N-(2-ethoxyphenyl)-N'-(4- ethylphenyl)ethylene diamide (CAS Reg. No. 23949-66-8; CANDUVOR VSU from Clariant), and N-(2-ethoxy-5-tert-butyl-phenyl)-N'-(2-ethylphenyl)ethylene diamide (CAS Reg. No. 35001-52-6; SANDUVOR EPU from Clariant).
  • Cyanoacrylate ultraviolet radiation absorbers include those having the structure
  • Ar 5 and Ar 6 are each independently an optionally substituted C 6 -Ci 8 aryl group, and R 22 is a C1-C12 alkyl group.
  • Illustrative cyanoacrylate ultraviolet radiation absorbers include ethyl-2-cyano-3,3-diphenyl acrylate (CAS Reg. No. 5232-99-5; UVINUL 3035 from BASF), and 2-ethylhexyl-2-cyano-3,3-diphenylacrylate (CAS Reg. No. 6197-30-4; UVINUL 3039 from BASF).
  • Hindered amine light stabilizers generally comprise a 5- or 6-membered ring comprising a nitrogen atom bonded to two quaternary carbons.
  • suitable hindered amine light stabilizers include those having the structure
  • the hindered amine light stabilizer is bis(2,2,6,6-tetramethyl-4-piperidinyl)sebacate, CAS Reg. No. 52829- 07-9.
  • Cycloaliphatic epoxy compounds include, for example, cyclopentene oxide, cyclohexene oxide, 4-vinylcyclohexene oxide, 4-vinylcyclohexene dioxide, 3,4-epoxycyclohexylmethyl 3',4'-epoxycyclohexylcarboxylate (CAS Reg. No.
  • A- alkoxymethylcyclohexene oxides acyloxymethylcyclohexene oxides, l,3-bis(2-(3,4- epoxycyclohexyl)ethyl)- 1 ,1 ,3,3-tetramethydisiloxane, 2-epoxy- 1 ,2,3,4-tetrahydronaphthalene, and the like, and mixtures thereof.
  • the total amount of ultraviolet radiation stabilizer composition is 0.4 to 10 weight percent, based on the total weight of the thermoplastic composition. Within this range, the ultraviolet radiation stabilizer composition can be 0.8 to 6 weight percent, specifically 1.2 to 3 weight percent. When present, the ultraviolet radiation absorber is typically used in an amount of 0.3 to 1.2 weight percent, specifically 0.6 to 0.8 weight percent, based on the total weight of the composition. When present, the hindered amine light stabilizer is typically used in an amount of 0.3 to 1.5 weight percent, specifically 0.6 to 1.2 weight percent, based on the total weight of the composition.
  • the cycloaliphatic epoxy compound is typically used in an amount of 0.1 to 0.6 weight percent, specifically 0.2 to 0.5 weight percent, more specifically 0.3 to 0.4 weight percent, based on the total weight of the composition.
  • the ultraviolet radiation stabilizer composition comprises 0.3 to 1.2 weight percent of a benzotriazole ultraviolet radiation absorber, 0.3 to 1.5 weight percent of a hindered amine light stabilizer, and 0.1 to 0.6 weight percent of a cycloaliphatic epoxy compound.
  • the ultraviolet radiation stabilizer composition is provided in the form of an ultraviolet radiation stabilizer masterbatch comprising the ultraviolet radiation stabilizer composition and the thermoplastic elastomer.
  • pre-compounding the ultraviolet radiation stabilizer composition with the thermoplastic elastomer unexpectedly improves the ultraviolet light resistance of the composition compared to compositions in which the ultraviolet radiation stabilizer composition is added separately or pre-compounded with the poly(arylene ether) component.
  • the ultraviolet light resistance of a poly(arylene ether) -containing composition could be improved by pre-compounding the ultraviolet radiation stabilizer with a component other than the poly(arylene ether).
  • the ultraviolet radiation stabilizer masterbatch is described as comprising the ultraviolet radiation stabilizer composition and the thermoplastic elastomer, it will be understood that the radiation stabilizer masterbatch can contain some or all of the total thermoplastic elastomer content of the thermoplastic composition. Similarly, the ultraviolet radiation stabilizer masterbatch can contain some or all of the total ultraviolet radiation stabilizer composition. In some embodiments, at least 50 weight percent, specifically at least 90 weight percent, more specifically 100 weight percent, of the ultraviolet radiation stabilizer composition is incorporated into the ultraviolet radiation stabilizer masterbatch. In some embodiments, at least 50 weight percent, specifically at least 90 weight percent, more specifically 100 weight percent, of the thermoplastic elastomer is incorporated into the ultraviolet radiation stabilizer masterbatch. Also, to the extent that the thermoplastic elastomer comprises two or more chemically distinct thermoplastic elastomer components, the radiation stabilizer masterbatch can contain some or all of the distinct elastomer components.
  • the ultraviolet radiation stabilizer masterbatch is prepared by melt-kneading the ultraviolet radiation stabilizer composition and the thermoplastic elastomer to produce an intimate blend. Illustrative examples of specific compounding conditions are provided in the working examples below.
  • the thermoplastic composition comprises less than or equal to 20 weight percent of rubber-modified polystyrene. It has been observed that incorporation of rubber- modified polystyrene in amounts greater than 20 weight percent is associated with reduced stability to ultraviolet radiation.
  • the composition comprises rubber- modified polystyrene in an amount less than or equal to 15 weight percent, specifically less than or equal to 10 weight percent, more specifically less than or equal to 5 weight percent, even more specifically less than or equal to 1 weight percent, yet more specifically less than or equal to 0.1 weight percent.
  • the composition excludes rubber-modified polystyrene. In this context, "excludes" means that no rubber-modified polystyrene is intentionally added to the composition.
  • the thermoplastic composition can, optionally, comprise additional components.
  • the thermoplastic composition further comprises polyethylene, polypropylene, or a mixture thereof.
  • This component is distinguished from the thermoplastic elastomer in that the terms "polyethylene” and “polypropylene” refer to homopolymers of ethylene and propylene, respectively, whereas the thermoplastic elastomer is by definition a copolymer.
  • the amount of the polyethylene, polypropylene, or a mixture thereof is 5 to 60 weight percent, based on the total weight of the thermoplastic composition.
  • the amount of the polyethylene, polypropylene, or a mixture thereof can be 10 to 40 weight percent, more specifically 15 to 30 weight percent.
  • the polyethylene and/or polypropylene is incorporated via melt kneading with the poly(arylene ether), the thermoplastic elastomer, the flame retardant, and the ultraviolet radiation stabilizer composition.
  • thermoplastic composition excludes polyethylene and polypropylene.
  • the thermoplastic composition comprises 4 to 12 weight percent of a polybutene, based on the total weight of the composition. Within this range, the polybutene amount can be 6 to 10 weight percent. In some embodiments, the polybutene has a number average molecular weight of 600 to 1,000 atomic mass units. These polybutene number average molecular weight values are uncorrected values measured by gel permeation chromatography using polystyrene standards. The polybutene is incorporated via melt kneading with the poly(arylene ether), the thermoplastic elastomer, the flame retardant, and the ultraviolet radiation stabilizer composition. [0062] In some embodiments the thermoplastic composition excludes polybutene.
  • thermoplastic composition comprises a white pigment.
  • Suitable white pigments include, for example, calcium carbonate, kaolin, talc, calcium sulfate, barium sulfate, titanium dioxide, zinc oxide, zinc sulfide, zinc carbonate, satin white, aluminum silicate, diatomaceous earth, calcium silicate, magnesium silicate, synthetic amorphous silica, colloidal silica, colloidal alumina, pseudo-boehmite, aluminum hydroxide, alumina, modified alumina, lithopone, zeolite, hydrated halloysite, magnesium carbonate, magnesium hydroxide, and mixtures thereof.
  • the white pigment is zinc sulfide, titanium dioxide (including rutile titanium dioxide), or a mixture thereof.
  • the white pigment is titanium dioxide.
  • the colorant is incorporated via melt kneading with the poly(arylene ether), the thermoplastic elastomer, the flame retardant, and the ultraviolet radiation stabilizer composition.
  • the thermoplastic composition excludes any polymer not taught herein as required or optional.
  • the thermoplastic composition excludes homopolystyrenes.
  • the thermoplastic composition excludes polyamides.
  • the thermoplastic composition is formed by melt kneading the ultraviolet radiation stabilizer masterbatch with the poly(arylene ether), the flame retardant, and any optional components.
  • Melt-kneading equipment is known in the art and includes single- screw and twin-screw type extruders and similar mixing devices that can apply shear to the components.
  • all components, including the ultraviolet radiation stabilizer masterbatch are added at the feedthroat of the extruder.
  • the poly(arylene ether) and the flame retardant are melt kneaded to form a first blend, which is then melt kneaded with the ultraviolet radiation stabilizer masterbatch.
  • the poly(arylene ether) comprises a poly(2,6-dimethyl-l,4-phenylene ether) having an intrinsic viscosity of 0.35 to 0.6 deciliter per gram measured at 25°C in chloroform;
  • the thermoplastic composition comprises 20 to 30 weight percent of the poly(arylene ether);
  • the thermoplastic elastomer comprises a polystyrene-poly(ethylene-butylene)-polystyrene triblock copolymer, a polystyrene- poly(ethylene-butylene-styrene)-polystyrene triblock copolymer, and a random copolymer of ethylene and propylene;
  • the thermoplastic composition comprises 25 to 35 weight percent of the thermoplastic elastomer;
  • the flame retardant comprises melamine polyphosphate and magnesium hydroxide;
  • the thermoplastic composition comprises 13 to 20 weight percent of the flame retardant;
  • the ultraviolet radiation stabilizer composition comprises 0.3 to 1.2 weight percent of
  • thermoplastic composition prepared according to the method, which is distinguished from prior art compositions by its improved stability to ultraviolet radiation.
  • thermoplastic composition prepared according to the above method and exhibiting a CIELAB color shift, ⁇ E, less than or equal to 2 measured according to ASTM D2244 after 300 hours exposure to xenon arc exposure according to ASTM D4459.
  • the thermoplastic composition exhibits a CIE lightness value, L*, value of at least 70 measured according to ASTM D2244-05.
  • the lightness value, L* is at least 80.
  • the lightness value, L* is 70 to 95, specifically 75 to 90, more specifically 80 to 90, still more specifically 85 to 88.
  • the composition can be flexible.
  • One objective correlate of the subject term "flexibility" is flexural modulus.
  • the thermoplastic composition exhibits a flexural modulus less than or equal to 1,000 megapascals, measured at 23 0 C according to ASTM D790-03.
  • the flexural modulus is 20 to 1,000 megapascals, specifically 20 to 500 megapascals, more specifically 50 to 200 megapascals, even more specifically 35 to 150 megapascals, still more specifically 50 to 100 megapascals.
  • thermoplastic composition is particularly useful for fabricating insulation for wire and cable, where the wire cable further comprises a conductor (e.g., an electrical conductor or a light conductor).
  • the invention includes the ultraviolet radiation stabilizer masterbatch itself.
  • an ultraviolet radiation stabilizer masterbatch comprising: 80 to 99 weight percent of a thermoplastic elastomer selected from the group consisting of hydrogenated block copolymers of an alkenyl aromatic compound and a conjugated diene, polyolefin block copolymers having a (hard) polyethylene or polypropylene block and (soft) block that is a copolymer of ethylene and a C 3 -C 12 olefin, random copolymers of ethylene and a C 3 -C 12 alpha-olefin, and mixtures thereof; and 1 to 20 weight percent of an ultraviolet radiation stabilizer composition comprising at least two ultraviolet stabilizing compounds selected from different subgroups of the group consisting of a first subgroup consisting of ultraviolet radiation absorbers, a second subgroup consisting of hindered amine light stabilizers, and a third subgroup consisting of cycloaliphatic epoxy compounds; wherein all weight percents are
  • the thermoplastic elastomer amount can be 85 to 98 weight percent, specifically 90 to 96 weight percent, more specifically 92 to 94 weight percent.
  • the ultraviolet radiation stabilizer composition amount can be 2 to 15 weight percent, specifically 4 to 10 weight percent, more specifically 6 to 8 weight percent.
  • the invention includes at least the following embodiments:
  • Embodiment 1 A method of forming a thermoplastic composition, comprising: melt-kneading 20 to 40 weight percent of a poly(arylene ether), 10 to 60 weight percent of a thermoplastic elastomer, 5 to 25 weight percent of a flame retardant, and 0.4 to 10 weight percent of an ultraviolet radiation stabilizer composition comprising at least two ultraviolet stabilizing compounds selected from different subgroups of the group consisting of a first subgroup consisting of ultraviolet radiation absorbers, a second subgroup consisting of hindered amine light stabilizers, and a third subgroup consisting of cycloaliphatic epoxy compounds to form a thermoplastic composition; wherein all weight percents are based on the total weight of the composition; wherein the ultraviolet radiation stabilizer composition is provided in the form of an ultraviolet radiation stabilizer masterbatch comprising the ultraviolet radiation stabilizer composition and the thermoplastic elastomer; and wherein the thermoplastic composition comprises less than or equal to 20 weight percent of rubber- modified polystyrene.
  • Embodiment 2 The method of embodiment 1, wherein the thermoplastic elastomer is selected from the group consisting of hydrogenated block copolymers of an alkenyl aromatic compound and a conjugated diene, polyolefin block copolymers having a polyethylene or polypropylene block and block that is a copolymer of ethylene and a C 3 -C 12 olefin, random copolymers of ethylene and a C 3 -C 12 alpha-olefin, and mixtures thereof.
  • the thermoplastic elastomer is selected from the group consisting of hydrogenated block copolymers of an alkenyl aromatic compound and a conjugated diene, polyolefin block copolymers having a polyethylene or polypropylene block and block that is a copolymer of ethylene and a C 3 -C 12 olefin, random copolymers of ethylene and a C 3 -C 12 alpha-olefin, and mixtures thereof.
  • Embodiment 3 The method of embodiment 1 or 2, wherein the thermoplastic elastomer comprises a polystyrene-poly(ethylene-propylene) diblock copolymer.
  • Embodiment 4 The method of embodiment 1 or 2, wherein the thermoplastic elastomer comprises a polystyrene-poly(ethylene-butylene)-polystyrene triblock copolymer.
  • Embodiment 5 The method of embodiment 1 or 2, wherein the thermoplastic elastomer comprises a polystyrene-poly(ethylene-butylene-styrene)-polystyrene triblock copolymer.
  • Embodiment 6 The method of embodiment 1 or 2, wherein the thermoplastic elastomer comprises a random copolymer of ethylene and propylene.
  • Embodiment 7 The method of any of embodiments 1, 2, 4, and 6, wherein the thermoplastic elastomer comprises a polystyrene-poly(ethylene-butylene)-polystyrene triblock copolymer and a random copolymer of ethylene and propylene.
  • Embodiment 8 The method of any of embodiments 1, 2, 4, 5, 6, and 7, wherein the thermoplastic elastomer comprises a polystyrene-poly(ethylene-butylene)- polystyrene triblock copolymer, a polystyrene-poly(ethylene-butylene-styrene) -polystyrene triblock copolymer, and a random copolymer of ethylene and propylene.
  • the thermoplastic elastomer comprises a polystyrene-poly(ethylene-butylene)- polystyrene triblock copolymer, a polystyrene-poly(ethylene-butylene-styrene) -polystyrene triblock copolymer, and a random copolymer of ethylene and propylene.
  • Embodiment 9 The method of any of embodiments 1-8, wherein the ultraviolet radiation stabilizer composition comprises 0.3 to 1.2 weight percent of a benzotriazole ultraviolet radiation absorber, 0.3 to 1.5 weight percent of a hindered amine light stabilizer, and 0.1 to 0.6 weight percent of a cycloaliphatic epoxy compound.
  • Embodiment 10 The method of any of embodiments 1-9, wherein the flame retardant is selected from the group consisting of organophosphate esters, metal dialkyl phosphinates, nitrogen-containing flame retardants, metal hydroxides, and mixtures thereof.
  • the flame retardant is selected from the group consisting of organophosphate esters, metal dialkyl phosphinates, nitrogen-containing flame retardants, metal hydroxides, and mixtures thereof.
  • Embodiment 11 The method of any of embodiments 1-10, wherein the flame retardant comprises melamine polyphosphate and magnesium hydroxide.
  • Embodiment 12 The method of any of embodiments 1-11, further comprising melt kneading 5 to 60 weight percent of polyethylene, polypropylene, or a mixture thereof with the poly(arylene ether), the thermoplastic elastomer, the flame retardant, and the ultraviolet radiation stabilizer composition.
  • Embodiment 13 The method of any of embodiments 1-12, further comprising melt kneading 4 to 12 weight percent of a polybutene with the poly(arylene ether), the thermoplastic elastomer, the flame retardant, and the ultraviolet radiation stabilizer composition.
  • Embodiment 14 The method of embodiment 13, wherein the polybutene has a number average molecular weight of 600 to 1,000 atomic mass units.
  • Embodiment 15 The method of any of embodiments 1-14, wherein the thermoplastic composition excludes rubber-modified polystyrene.
  • Embodiment 16 The method of any of embodiments 1-15, wherein the melt- kneading the poly(arylene ether), the thermoplastic elastomer, the flame retardant, and the ultraviolet radiation stabilizer comprises melt kneading the poly(arylene ether) and the flame retardant to form a first blend, and melt kneading with the first blend with the ultraviolet radiation stabilizer masterbatch.
  • Embodiment 17 The method of embodiment 1, wherein the poly(arylene ether) comprises a poly(2,6-dimethyl-l,4-phenylene ether) having an intrinsic viscosity of 0.35 to 0.6 deciliter per gram measured at 25°C in chloroform; wherein the thermoplastic composition comprises 20 to 30 weight percent of the poly(arylene ether); wherein the thermoplastic elastomer comprises a polystyrene-poly(ethylene-butylene)-polystyrene triblock copolymer, a polystyrene-poly(ethylene-butylene-styrene) -polystyrene triblock copolymer, and a random copolymer of ethylene and propylene; wherein the thermoplastic composition comprises 25 to 35 weight percent of the thermoplastic elastomer; wherein the flame retardant comprises melamine polyphosphate and magnesium hydroxide; wherein the thermoplastic composition comprises 13 to 20 weight percent of the flame retardant;
  • Embodiment 18 A thermoplastic composition prepared according to the method of embodiment 17 and exhibiting a CIELAB color shift, ⁇ E, less than or equal to 2 measured according to ASTM D2244 after 300 hours exposure to xenon arc exposure according to ASTM D4459.
  • Embodiment 19 The thermoplastic composition of embodiment 18, further exhibiting a CIE lightness value, L*, value of at least 70 measured according to ASTM D2244.
  • Embodiment 20 The composition of embodiment 18 or 19, further exhibiting a flexural modulus less than or equal to 1,000 megapascals, measured at 23°C according to ASTM D790.
  • Embodiment 21 An article comprising the thermoplastic composition of any of embodiments 18-20.
  • Embodiment 22 The article of embodiment 21, wherein the article comprises cable insulation comprising the thermoplastic composition.
  • Embodiment 23 An ultraviolet radiation stabilizer masterbatch, comprising: 80 to 99 weight percent of a thermoplastic elastomer selected from the group consisting of hydrogenated block copolymers of an alkenyl aromatic compound and a conjugated diene, polyolefin block copolymers having a polyethylene or polypropylene block and block that is a copolymer of ethylene and a C3-C12 olefin, random copolymers of ethylene and a C3-C12 alpha-olefin, and mixtures thereof, and 1 to 20 weight percent of an ultraviolet radiation stabilizer composition comprising at least two ultraviolet stabilizing compounds selected from different subgroups of the group consisting of a first subgroup consisting of ultraviolet radiation absorbers, a second subgroup consisting of hindered amine light stabilizers, and a third subgroup consisting of cycloaliphatic epoxy compounds; wherein all weight percents are based on the total weight of the ultraviolet radiation stabilizer masterbatch.
  • Table 1 lists the components used in the working examples. Table 1
  • An ultraviolet radiation stabilizer masterbatch in the thermoplastic elastomer polystyrene-poly(ethylene-butylene) diblock copolymer (SEP) was prepared by melt-kneading 96.67 weight percent of SEP with 1.11 weight percent of 2-hydroxy-4-w- octoxybenzophenone, and 2.22 weight percent of the hindered amine light stabilizer bis(2,2,6,6-teramethyl-4-piperidinyl) sebacate.
  • a corresponding ultraviolet radiation stabilizer masterbatch in high-impact polystyrene (HIPS) instead of SEP was also prepared.
  • HIPS high-impact polystyrene
  • Compounding was conducted using a Prism co-rotating twin-screw extruder having a 24-millimeter screw diameter.
  • the extrusion barrel setpoints were Zone 1 (Feed throat, unheated), Zone 2 (80 0 F, 27°C), Zone 3 (250 0 F, 121°C), Zone 4 (300 0 F, 149°C), Zone 5 (325°F, 163°C), Zone 6 (350 0 F, 177°C), Zone 7 (350 0 F, 177°C), Zone 8 (350 0 F, 177°C), Die (350 0 F, 177°C).
  • the Feed Rate was 55 pounds/hour (25 kilograms/hour), the screw speed was set at 350 revolutions per minute (rpm), and the machine torque was 75%.
  • the extruded strands were cooled in a 5 foot (1.5 meter) long water bath, and pelletized using a pelletizer.
  • An attempt to prepare a corresponding ultraviolet radiation stabilizer masterbatch in polystyrene-polybutadiene- polystyrene triblock copolymer (SBS) was unsuccessful because the material would not strand, and was instead spitting out of the die. The material recovered was darker and yellower than the other blends, suggesting degradation.
  • SBS polystyrene-polybutadiene- polystyrene triblock copolymer
  • Three thermoplastic compositions were prepared using the components specified in Table 2, where the ultraviolet radiation stabilizer masterbatch in SEP is abbreviated "SEP/UVA", and the ultraviolet radiation stabilizer masterbatch in HIPS is abbreviated "HIPS/UVA".
  • thermoplastic compositions were prepared using a Prism co-rotating twin-screw extruder having a 24-millimeter screw diameter.
  • the extrusion barrel setpoints were Zone 1 (Feed throat, unheated), Zone 2 (250 0 F, 121°C), Zone 3 (400 0 F, 204 0 C), Zone 4 (450 0 F, 232°C), Zone 5 (475°F, 246°C), Zone 6 (510 0 F, 266°C), Zone 7 (520 0 F), Zone 8 (520 0 F, 271°C), Die (520 0 F, 271°C).
  • the Feed Rate was 40 pounds/hr (18 kilograms/hour), and the screw speed was set at 600 rpm.
  • the liquid BPADP flame retardant was added in using a downstream injection port on the extruder.
  • the extruded strands were cooled in a 5 foot (1.5 meter) long water bath, and pelletized using a pelletizer.
  • Plaques of dimensions 5.08 centimeters x 7.62 centimeters x 0.254 centimeter (2 inches x 3 inches x 0.100 inch) were molded using a Nissei molding machine with barrel set points of Rear (470 0 F, 243°C), Mid (490 0 F, 254°C), Front (500 0 F, 260 0 C), Nozzle (500 0 F, 260 0 C).
  • the tool temperature (mold face) was set at 170 0 F (ITC).
  • the injection time was set for 14 seconds, the cooling time for 20 seconds, and the hold time for 30 seconds.
  • ⁇ E [( ⁇ L*) 2 +( ⁇ a*) 2 +( ⁇ b*) 2 ] 1/2
  • ⁇ L* Li*-L2* and wherein Li*, ai*, and bi* are the lightness, red-green coordinate, and yellow-blue coordinate, respectively, prior to the exposure to the test, and L 2 *, a 2 *, and b 2 * are lightness, red-green coordinate, and yellow-blue coordinate, respectively, after exposure to the test.
  • Comparative Example 1 is a control composition in which the ultraviolet radiation stabilizer composition was present in the thermoplastic composition but not pre-compounded with any other component. Comparative Example 1 exhibits ⁇ E values of 10.22 and 14.21 at 300 and 500 hours exposure, respectively.
  • Example 1 which was very similar to Comparative Example 1 except that the ultraviolet radiation stabilizer composition was pre-compounded with the SEP component, exhibited smaller ⁇ E values (improved ultraviolet stability) of 8.85 and 11.70 at 300 and 500 hours exposure, respectively.
  • Comparative Example 2 in which high-impact polystyrene was substituted for half of the SEP and in which the ultraviolet radiation stabilizer composition was provided half as a masterbatch in SEP and the other half as a masterbatch in HIPS, exhibited higher ⁇ E values (worse ultraviolet stability) than Comparative Example 1.
  • thermoplastic elastomer the thermoplastic polyolefin, or both.
  • the barrel set temperatures were 200-220-250-250 0 C from zone 1 (extruder feedthroat) to the die.
  • the total feed rate was set to 30 pounds/hour (14 kilograms/hour) and the screw rotated at 300 rpm. Flame retardant was added directly to the extruder at barrel 2 with a dedicated liquid pump.
  • Extruded strands were cooled through a 5 foot (1.5 meter) long circulating water bath before being chopped into granules by a Labtech pelletizer. Plaques of dimensions 5.08 centimeters x 7.62 centimeters x 0.254 centimeter (2 inches x 3 inches x 0.100 inch) were injection-molded on a Van Dorn 120T molding machine with barrel set temperatures of 450°F/232°C (rear) to 500°F/260°C (nozzle). The tool temperature was set to 120°F/49°C and the cycle time was about 45 seconds.
  • the first ultraviolet radiation stabilizer masterbatch designated "SEBS/UVA” in Table 3, consisted of 51.24 parts by weight SEBS-RP6936, 21.57 parts by weight TPE, 21.57 parts by weight SEBS-KG1657, 0.89 parts by weight cycloaliphatic epoxy, 2.02 parts by weight benzotriazole UVA, and 2.70 parts by weight HALS.
  • the second ultraviolet radiation stabilizer masterbatch designated "PPE/FR/UVA” in Table 3, consisted of 82.96 parts by weight PPE, 1.26 parts by weight cycloaliphatic epoxy, 2.86 parts by weight benzotriazole UVA, 3.82 parts by weight HALS, and 9.1 parts by weight BPADP.
  • the third ultraviolet radiation stabilizer masterbatch designated "PPE/UVA" in Table 3, consisted of 92.06 parts by weight PPE, 1.26 parts by weight cycloaliphatic epoxy, 2.86 parts by weight benzotriazole UVA, and 3.82 parts by weight HALS.
  • Comparative Example 3 is a control composition in which the ultraviolet radiation stabilizer composition was present in the thermoplastic composition but not pre-compounded with any other component. Comparative Example 3 exhibited ⁇ E values of 2.73 and 2.59 at 300 and 500 hours exposure, respectively.
  • Example 2 which was similar to Comparative Example 3 except that the ultraviolet radiation stabilizer composition was pre-compounded with the SEBS-RP6936, TPE, and SEBS-KG1657 components, exhibited smaller ⁇ E values (improved ultraviolet stability) of 0.97 and 1.24 at 300 and 500 hours exposure, respectively.
  • Example 3 was identical to Example 2, except that the SEBS/UVA masterbatch was added to a downstream section of the extruder rather than the feed throat of the extruder when compounding the thermoplastic composition.
  • Example 3 exhibited ⁇ E values of 1.02 and 1.18 at 300 and 500 hours exposure, respectively, which are much lower (better) than the corresponding values for Comparative Example 4, which has similar component amounts but was not prepared using an ultraviolet radiation stabilizer masterbatch.
  • Comparative Examples 4 and 5 incorporated PPE/FR/UVA and PPE/UVA masterbatches, respectively. Their ⁇ E values at 300 and 500 hours were significantly higher (worse) than those for Comparative Example 3, in which the ultraviolet radiation stabilizer composition was not incorporated as a masterbatch. Given the known ultraviolet sensitivity of the poly(arylene ether) component, it is very surprising that pre-compounding the ultraviolet radiation stabilizer composition with the poly(arylene ether) has a detrimental effect on the composition.

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  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
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Abstract

Selon la présente invention, la stabilité à la lumière ultraviolette d'une composition de poly(arylène éther)/élastomère est améliorée quand les stabilisants à l'action de la lumière ultraviolette sont pré-mélangés avec au moins une partie du composant élastomère de la composition. Un procédé de préparation de la composition de poly(arylène)éther est décrit, ainsi que la composition elle-même et des articles préparés à partir de celle-ci.
PCT/US2009/054388 2008-09-11 2009-08-20 Composition de poly(arylène éther), procédé, et article selon l'invention WO2010030478A2 (fr)

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012007124A1 (fr) * 2010-07-13 2012-01-19 Clariant International Ltd Combinaison agent ignifugeant-stabilisant pour polymères thermoplastiques
WO2012075621A1 (fr) * 2010-12-07 2012-06-14 Sabic Innovative Plastics Ip B.V. Composition de poly(éther arylénique)-polyoléfine et son utilisation dans l'isolation et le gainage de fil métallique et de câble
US20120217037A1 (en) * 2011-02-25 2012-08-30 Kouichi Nakashima Method of forming coated conductor and coated conductor formed thereby
CN103525073A (zh) * 2013-10-12 2014-01-22 绿宝电缆（集团）有限公司 一种聚苯醚电缆料
US8637131B1 (en) 2012-11-30 2014-01-28 Sabic Innovative Plastics Ip B.V. Poly(phenylene ether) article and composition
WO2013121363A3 (fr) * 2012-02-17 2014-02-20 Sabic Innovative Plastics Ip B.V. Composition de poly(phénylène éther) résistant aux taches et au changement de couleur
US8669309B1 (en) 2012-09-26 2014-03-11 Sabic Innovative Plastics Ip B.V. Poly(phenylene ether) composition and article
US8703851B2 (en) 2012-09-26 2014-04-22 Sabic Innovative Plastics Ip B.V. Poly(phenylene ether) composition and article
US8703852B2 (en) 2011-06-03 2014-04-22 Sabic Innovative Plastics Ip B.V. Impact-resistant poly(arylene ether) resins with improved clarity
WO2014176119A1 (fr) * 2013-04-25 2014-10-30 Polyone Corporation Élastomères thermoplastiques retardateurs de flamme
US8957143B2 (en) 2011-06-03 2015-02-17 Sabic Global Technologies B.V. Impact-resistant poly(arylene ether) resins with improved clarity
WO2015023381A1 (fr) * 2013-08-16 2015-02-19 Exxonmobil Chemical Patents Inc. Compositions de poly(éther d'arylène) stabilisées et leurs procédés de préparation
CN105121547A (zh) * 2013-12-10 2015-12-02 Lg化学株式会社 聚(亚芳基醚)阻燃树脂组合物以及非交联阻燃电缆
US20160024303A1 (en) * 2014-02-28 2016-01-28 Lg Chem, Ltd. FIRE RETARDANT THERMOPLASTIC RESIN COMPOSITION AND ELECTRIC WIRE COMPRISING THE SAME (As Amended)
WO2017187286A1 (fr) * 2016-04-25 2017-11-02 Sabic Global Technologies B.V. Composition de poly(éther de phénylène) et article en poly(éther de phénylène)
US11345814B2 (en) * 2016-02-29 2022-05-31 Shpp Global Technologies B.V. Poly(phenylene ether) composition and jacketed cable comprising same

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440887A (en) * 1981-01-28 1984-04-03 Sandoz Ltd. 4-Aminomethylpolyalkylpiperidines useful as light stabilizers
US4493915A (en) * 1982-10-29 1985-01-15 General Electric Company Light stable thermoplastic polyphenylene ether resin compositions comprising purple anthrapyridone dye or yellow quinophtalone dye
US4551494A (en) * 1982-10-29 1985-11-05 General Electric Company Antistatic polyphenylene ether compositions
US5055494A (en) * 1987-10-01 1991-10-08 General Electric Co. Method of improving the resistance of polyphenylene ether articles to sunlight, and articles improved by this method
US5122555A (en) * 1989-08-07 1992-06-16 Akzo Nv Uv-stabilization of polymers using nitro compounds
US20080206468A1 (en) * 2007-02-28 2008-08-28 Steven Raymond Klei Poly(arylene ether) composition, method, and article
US20080206449A1 (en) * 2007-02-28 2008-08-28 Steven Raymond Klei Poly(arylene ether) composition, method, and article

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440887A (en) * 1981-01-28 1984-04-03 Sandoz Ltd. 4-Aminomethylpolyalkylpiperidines useful as light stabilizers
US4493915A (en) * 1982-10-29 1985-01-15 General Electric Company Light stable thermoplastic polyphenylene ether resin compositions comprising purple anthrapyridone dye or yellow quinophtalone dye
US4551494A (en) * 1982-10-29 1985-11-05 General Electric Company Antistatic polyphenylene ether compositions
US5055494A (en) * 1987-10-01 1991-10-08 General Electric Co. Method of improving the resistance of polyphenylene ether articles to sunlight, and articles improved by this method
US5122555A (en) * 1989-08-07 1992-06-16 Akzo Nv Uv-stabilization of polymers using nitro compounds
US20080206468A1 (en) * 2007-02-28 2008-08-28 Steven Raymond Klei Poly(arylene ether) composition, method, and article
US20080206449A1 (en) * 2007-02-28 2008-08-28 Steven Raymond Klei Poly(arylene ether) composition, method, and article

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9534109B2 (en) 2010-07-13 2017-01-03 Clariant International Ltd. Flame retardant-stabilizer combination for thermoplastic polymers
WO2012007124A1 (fr) * 2010-07-13 2012-01-19 Clariant International Ltd Combinaison agent ignifugeant-stabilisant pour polymères thermoplastiques
WO2012075621A1 (fr) * 2010-12-07 2012-06-14 Sabic Innovative Plastics Ip B.V. Composition de poly(éther arylénique)-polyoléfine et son utilisation dans l'isolation et le gainage de fil métallique et de câble
US20120217037A1 (en) * 2011-02-25 2012-08-30 Kouichi Nakashima Method of forming coated conductor and coated conductor formed thereby
US8703852B2 (en) 2011-06-03 2014-04-22 Sabic Innovative Plastics Ip B.V. Impact-resistant poly(arylene ether) resins with improved clarity
US8957143B2 (en) 2011-06-03 2015-02-17 Sabic Global Technologies B.V. Impact-resistant poly(arylene ether) resins with improved clarity
WO2013121363A3 (fr) * 2012-02-17 2014-02-20 Sabic Innovative Plastics Ip B.V. Composition de poly(phénylène éther) résistant aux taches et au changement de couleur
US8669309B1 (en) 2012-09-26 2014-03-11 Sabic Innovative Plastics Ip B.V. Poly(phenylene ether) composition and article
US8703851B2 (en) 2012-09-26 2014-04-22 Sabic Innovative Plastics Ip B.V. Poly(phenylene ether) composition and article
US8637131B1 (en) 2012-11-30 2014-01-28 Sabic Innovative Plastics Ip B.V. Poly(phenylene ether) article and composition
WO2014176119A1 (fr) * 2013-04-25 2014-10-30 Polyone Corporation Élastomères thermoplastiques retardateurs de flamme
US9988532B2 (en) 2013-04-25 2018-06-05 Polyone Corporation Flame retardant thermoplastic elastomers
WO2015023381A1 (fr) * 2013-08-16 2015-02-19 Exxonmobil Chemical Patents Inc. Compositions de poly(éther d'arylène) stabilisées et leurs procédés de préparation
US9815946B2 (en) 2013-08-16 2017-11-14 Exxonmobil Chemical Patents Inc. Stabilized poly(arylene ether) compositions and methods of making them
CN103525073A (zh) * 2013-10-12 2014-01-22 绿宝电缆（集团）有限公司 一种聚苯醚电缆料
CN103525073B (zh) * 2013-10-12 2016-03-02 绿宝电缆（集团）有限公司 一种聚苯醚电缆料
CN105121547A (zh) * 2013-12-10 2015-12-02 Lg化学株式会社 聚(亚芳基醚)阻燃树脂组合物以及非交联阻燃电缆
US9631091B2 (en) * 2013-12-10 2017-04-25 Lg Chem, Ltd. Poly (arylene ether) flame retardant resin composition and non-crosslinked flame retardant cable
US20160017146A1 (en) * 2013-12-10 2016-01-21 Lg Chem, Ltd. Poly (arylene ether) flame retardant resin composition and non-crosslinked flame retardant cable
JP2016515160A (ja) * 2014-02-28 2016-05-26 エルジー・ケム・リミテッド 難燃性熱可塑性樹脂組成物及びそれを含む電線
US20160024303A1 (en) * 2014-02-28 2016-01-28 Lg Chem, Ltd. FIRE RETARDANT THERMOPLASTIC RESIN COMPOSITION AND ELECTRIC WIRE COMPRISING THE SAME (As Amended)
US9822252B2 (en) * 2014-02-28 2017-11-21 Lg Chem, Ltd. Fire retardant thermoplastic resin composition and electric wire comprising the same
US11345814B2 (en) * 2016-02-29 2022-05-31 Shpp Global Technologies B.V. Poly(phenylene ether) composition and jacketed cable comprising same
WO2017187286A1 (fr) * 2016-04-25 2017-11-02 Sabic Global Technologies B.V. Composition de poly(éther de phénylène) et article en poly(éther de phénylène)

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