WO2025190859A1 - Compositions de polycarbonate contenant des unités monomères de biphénols et de bisphénols à pont acétylène - Google Patents

Compositions de polycarbonate contenant des unités monomères de biphénols et de bisphénols à pont acétylène

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Publication number
WO2025190859A1
WO2025190859A1 PCT/EP2025/056454 EP2025056454W WO2025190859A1 WO 2025190859 A1 WO2025190859 A1 WO 2025190859A1 EP 2025056454 W EP2025056454 W EP 2025056454W WO 2025190859 A1 WO2025190859 A1 WO 2025190859A1
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WO
WIPO (PCT)
Prior art keywords
triple bond
phenol groups
composition according
bisphenols
percent
Prior art date
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Pending
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PCT/EP2025/056454
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English (en)
Inventor
Abidin Balan
Chiel Mertens
Pascal E.R.E.J. Lakeman
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Trinseo Europe GmbH
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Trinseo Europe GmbH
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Publication date
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Publication of WO2025190859A1 publication Critical patent/WO2025190859A1/fr
Pending legal-status Critical Current
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Classifications

    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/045—Aromatic polycarbonates containing aliphatic unsaturation
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/22—General preparatory processes using carbonyl halides
    • C08G64/24—General preparatory processes using carbonyl halides and phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates

Definitions

  • Polycarbonate and copolymers containing carbonate units are utilized in a variety of molded structures.
  • Polycarbonates and copolymers containing carbonate units form molded structures that are rigid.
  • the molded structures may be used for a variety of uses, including cases for electronics, automobile parts, medical devices, home appliances, loud-speakers, home furnishings and the like. Fire retardancy of such structures is an important safety consideration. The market continues to demand improved fire retardancy while maintaining the premium properties of molded structures.
  • the use of PFAS compounds in polycarbonate compositions as flame retardants is common and such compounds provide excellent flame retardancy, see US 10100192 and US 2023/0167296, incorporated by reference in their entirety for all purposes.
  • Phosphorous based compounds are also utilized in polycarbonate compositions to impact flame retardance, see WO2019/115506 incorporated by reference herein in its entirety for all purposes. There is a concern relative to the use of PFAS compounds in polycarbonate compositions. Other fire retardants can plasticize the polycarbonate compositions and add significant cost to polycarbonate compositions.
  • compositions which are fire retardant wherein the fire retardant additives are eliminated or the amounts thereof are reduced, the compositions having the desired fire retardancy while maintaining the premium properties of molded products containing polycarbonates, such as excellent tensile strength at yield, tensile strength at break, tensile elongation at yield, tensile elongation at break, Notched Izod impact strength, and the like.
  • molded compositions prepared from such compositions that exhibit improved fire retardance and excellent properties.
  • polycarbonate compositions containing monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups, one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond located between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom.
  • the composition may comprise one or more polymers wherein the one or more polymers contain monomer units derived from each of one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO2- between the phenol groups, one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups.
  • the composition may be a blend of polymers having such units.
  • the polymers may further contain end capping groups or pendant groups having acetylenic groups, triple bonds. Such pendant groups or end capping groups may be disposed on any of the disclosed polymers.
  • Such pendant groups or end capping groups may be disposed on any of the disclosed polymers having monomer units derived from one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups.
  • the compositions may comprise a sufficient amount of monomer units derived from each of one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups such that the composition has enhanced fire retardant properties.
  • compositions may comprise a sufficient amount of monomer units derived from each of one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups, diphenols having pendant triple bonds from such diphenols and/or endcapping units having a triple bond such that the composition has enhanced fire retardant properties.
  • the composition may contain the biphenol monomer units present in an amount of about 5 to about 30 mole percent and the triple bond containing based monomer units and or endcapping units present in an amount of about 5 to about 30 mole percent, wherein the total amount of the biphenol monomer units and the triple bond containing monomer units is from about 20 to 40 mole percent wherein the mole percent is based on the total moles of monomer units present in the polymer.
  • the one or more bisphenols having a hydrocarbylene group, -O-, - SO-, -CO-, -S-, or a -SO 2 - between the phenol groups may correspond to the formula
  • the biphenol having a direct bond between the phenol groups may correspond to the formula
  • the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups correspond to one of the formulas, wherein:
  • A is separately in each occurrence C 1-5 alkylene, C 2-5 alkylidene, C 5-6 cycloalkylidene, -O-, -SO- , -CO-, -S-, -SO2-, or C 6-12 arylene, on to which other aromatic rings, which optionally contain hetero atoms, can be condensed;
  • B is separately in each occurrence a C 1-12 alkyl or a halogen;
  • D is separately in each occurrence a C 2 to 2o alkynylene group containing a triple bond in the backbone or a C 2 to2o alkylene group, C 6 -is arylene group or C 7-24 alkarylene group, wherein the triple bond may be pendant from such groups;
  • G is a direct bond or a linking group capable of bonding to the diphenolic ring and the triple bond; and x in each case is mutually independently 0, 1 , or 2.
  • the one or more polymers of the composition may comprise polymer units of units of the one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups may correspond to the formula:
  • one or more biphenols having a direct bond between the phenol groups may correspond to the formula; and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups may correspond to one of the formulas; wherein A, B, D, G and x are as described herein.
  • a terpolymer comprising each of the one or more monomers described wherein the one or more polymers contain monomer units derived from each of one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups, one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom.
  • composition comprising a blend of polymers wherein the first polymer is a polycarbonate polymer having monomer units derived from one or more biphenols having a direct bond between the phenol groups and the second is a polycarbonate polymer having monomer units derived from one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups wherein the triple bond may be disposed between the phenol groups or be pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom.
  • the first polymer, the second polymer or both contain monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO2- between the phenol groups or the blend contains a third polymer which is a polycarbonate polymer derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups.
  • the first polymer is a polycarbonate homopolymer having monomer units derived from one or more biphenols having a direct bond between the phenol groups and the second is a polycarbonate homopolymer having monomer units derived from one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and the third polymer which is a polycarbonate homopolymer derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO2- between the phenol groups.
  • composition comprising the blend of two polymers wherein the first polymer is a polycarbonate polymer having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups and biphenol having a direct bond between the phenol groups and the second is polymer having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups, and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant.
  • compositions disclosed herein may exhibit a percent char of greater than 20 percent when measured using thermogravimetric analysis at 800 °C in nitrogen wherein there is no additional flame retardant or antidrip agent present.
  • the compositions disclosed and articles prepared from the compositions disclosed may exhibit a UL94 V0@1.5 mm flame retardancy.
  • the compositions disclosed and articles prepared from the compositions disclosed may exhibit a percent char of greater than 20 percent when measured using thermogravimetric analysis at 800 °C in nitrogen wherein there is no additional flame retardant or antidrip agent present.
  • compositions disclosed and articles prepared from the compositions disclosed may exhibit a UL94 V0@1.5 mm flame retardancy wherein there is no additional flame retardant or antidrip agent present.
  • the articles may be used in automobiles, trains, buses, recreation vehicles (RVs) and the like.
  • Hydrocarbyl refers to a group containing one or more carbon atom backbones and hydrogen atoms, which may optionally contain one or more heteroatoms. Where the hydrocarbyl group contains heteroatoms, the heteroatoms may form one or more functional groups well known to one skilled in the art. Hydrocarbyl groups may contain cycloaliphatic, aliphatic, aromatic or any combination of such segments. The aliphatic segments can be straight or branched. The aliphatic and cycloaliphatic segments may include one or more double and/or triple bonds.
  • hydrocarbyl groups are alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, alkaryl and aralkyl groups. Cycloaliphatic groups may contain both cyclic portions and noncyclic portions.
  • Hydrocarbylene means a hydrocarbyl group or any of the described subsets having more than one valence, such as alkylene, alkenylene, alkynylene, arylene, cycloalkylene, cycloalkenylene, alkarylene and aralkylene.
  • Alkynylene refers to an aliphatic group containing a triple bond.
  • Valence as used herein means a covalent bond between a hydrocarbyl or hydrocarbylene group and another group such as a carbonyl, oxygen, nitrogen or sulfur containing group or atom, or the referenced base compound.
  • percent by weight or parts by weight refer to, or are based on, the weight of the compositions unless otherwise specified.
  • Tg is the temperature or temperature range at which a polymeric material shows an abrupt change in its physical properties, including, for example, mechanical strength. Tg can be determined by differential scanning calorimetry (DSC) according to ASTM D3418-15.
  • the molecular weight in this disclosure is determined by gel permeation chroma tography using narrow polystyrene (£> ⁇ 1 .2) and a broad range polycarbonate standard (£> > 1 .5) standards and tetrahydrofuran solvent performed at 40 °C.
  • the melt flow rate is determined by measuring the grams passing through a standard die (2.095 x 8 mm) for 10 minutes (g/10 min) as determined at 300°C under a load of 1 .2 kg according to ISO 1133 standard.
  • Polycarbonate as used herein means a polymer containing carbonate units.
  • Such polymers may be homopolymers consisting essentially of carbonate monomer units (substantially all or 100 percent of carbonate monomer units) or copolymers containing one or more other monomer units (co-monomer units) and carbonate units.
  • Such copolymers may be block copolymers containing two or more blocks of different monomer units or may be random copolymers with the different monomer units randomly located along the polymer backbone.
  • the other monomer units may comprise any monomer units that do not negatively impact the inherent properties of polycarbonates, for instance heat resistance, impact resistance, moldability, flexural modulus, bending strength, haze and transparency, where required for the intended use.
  • exemplary comonomer units are ester units, polysiloxane units, and the like.
  • the amount of carbonate monomer units in copolycarbonates is selected such that the resulting polymer retains the desirable properties of polycarbonates, as disclosed herein.
  • the copolycarbonates may contain greater than 50 mole percent carbonate monomer units, about 75 mole percent or greater carbonate monomer units, about 80 mole percent or greater carbonate monomer units or about 85 mole percent or greater carbonate monomer units.
  • the copolycarbonates may contain 100 percent or less carbonate monomer units, about 99 mole percent or less carbonate monomer units, about 97 mole percent or less carbonate monomer units or about 95 mole percent or less carbonate monomer units.
  • the copolycarbonates may contain about 1 mole percent or greater co-monomer units, about 3 mole percent or greater co-monomer units or about 5 mole percent or greater co-monomer units.
  • the copolycarbonates may contain less than 50 mole percent comonomer units, about 25 mole percent or less co-monomer units, about 20 mole percent or less co-monomer units or about 15 mole percent or less co-monomer units.
  • the polycarbonate units may contain aromatic units in the backbone of the polymer.
  • the polycarbonate compositions contain polycarbonates comprising a polymer having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, - CO-, -S-, or a -SO2- between the phenol groups.
  • the hydrocarbylene group between the phenol groups of the one or more bisphenols having a hydrocarbylene group comprise C 1.5 alkylene, a C 2-5 alkylidene, a C 5-6 cycloalkylidene, -O-, -SO-, -CO-, -S-, -SO 2 -, or a C 6-12 arylene, on to which other aromatic rings, which optionally contain hetero atoms.
  • the hydrocarbylene group between the phenol groups of the one or more bisphenols having a hydrocarbylene group comprise a C 1. 5 alkylene.
  • the one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups may correspond to the formula, occurrence C 1.5 alkylene, C 2-5 alkylidene, C 5-6 cycloalkylidene, -O-, -SO-, -CO-, -S-, -SO 2 -, or C 6-12 arylene, on to which other aromatic rings, which may optionally contain hetero atoms, can be condensed;
  • B is separately in each occurrence a C 1.12 alkyl or a halogen; and x in each case is mutually independently 0, 1 , or 2.
  • B may be separately in each occurrence a methyl or chlorine and/or bromine
  • the polycarbonate compositions contain monomer units derived from one or more biphenols having a direct bond between the phenol groups.
  • the biphenols having a direct bond between the phenol groups may correspond to the formula, wherein B and x are as defined herein.
  • the monomer units derived from the one or more biphenols having a direct bond between the phenol groups may correspond to the formula; wherein B and x are as defined.
  • the polycarbonate compositions may contain monomer units derived from one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom.
  • the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom may correspond to one of the formulas, wherein B and x are as defined herein; and D is separately in each occurrence a C 2 to 20 alkynylene group containing a triple bond in the backbone or a C 2 to2o alkylene group, C 6 -is arylene group or C 7-24 alkarylene group, wherein a triple bond may be pendant from such groups; and G is a direct bond or a linking group capable of bonding to the diphenolic ring and the triple bond.
  • D may be separately in each occurrence a C 2-20 alkynylene group containing a triple bond.
  • the monomer units derived from the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups may correspond to one of the formulas;
  • G may be a Ci. 2 o hydrocarbylene group, or a C1-20 alkylene, arylene, alkyl substituted arylene and the like.
  • the one or more biphenols having a direct bond between the phenol groups and the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond are present in the compositions in an amount sufficient to improve the flame retardant properties of the composition including the UL94 flame retardancy, charring properties and antidrip properties.
  • Each of the one or more biphenols having a direct bond between the phenol groups and the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond may be present in an amount of about 5 mole percent by weight or greater based on the weight of the polycarbonate compositions, about 10 mole percent by weight or greater, about 15 mole percent or greater, about 20 mole percent or greater, about 30 mole percent by greater, about 40 mole percent or greater or about 50 mole percent by weight or greater.
  • Each of the one or more biphenols having a direct bond between the phenol groups and the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond may be present in an amount of about 70 mole percent by weight or less, about 60 mole percent or less, about 50 mole percent by weigh to or less, about 40 mole percent or less, about 30 mole percent by weight or less, about 20 mole percent or greater or about 15 mole percent by weight or less.
  • the polymer composition may comprise one or more homopolymers having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO2- between the phenol groups, one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond.
  • the polymer composition may comprise one or more copolymers having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO2- between the phenol groups, one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups.
  • the polymer composition may comprise one or more terpolymers having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups, one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond.
  • the polymer compositions may comprise a mixture of the recited homopolymers.
  • the polymer compositions may comprise a mixture of homopolymers and copolymers or terpolymers as recited.
  • the polymer compositions may comprise a mixture of copolymers and terpolymers as recited.
  • the polymer composition may comprise a mixture of one or more homopolymers having monomer units one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond.
  • Such mixture may contain higher amount of each homopolymer.
  • the polymer composition may comprise a copolymer of having monomer units one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond.
  • Such mixture may contain higher amount of each of the monomer units recited.
  • the polymer compositions may comprise one or more terpolymers, copolymers or homopolymers containing one or more bisphenols having a hydrocarbylene group, -O-, -SO-, - CO-, -S-, or a -SO2- between the phenol groups.
  • each of the one or more biphenols having a direct bond between the phenol groups and the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond may be present in an amount of about 5 mole percent by weight or greater based on the weight of the polycarbonate compositions, about 10 mole percent by weight or greater, about 15 mole percent or greater about 20 mole percent or greater or about 30 mole percent by greater.
  • each of the one or more biphenols having a direct bond between the phenol groups and the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond may be present in an amount of about 30 mole percent by weight or less, about 20 mole percent or less or about 15 mole percent by weight or less.
  • the total amount of the one or more biphenols having a direct bond between the phenol groups and the one or more bisphenols having a hydrocarbylene group containing a triple bond or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond may be 20 mole percent or greater, 25 mole percent or greater or 30 mole percent or greater.
  • the total amount of the one or more biphenols having a direct bond between the phenol groups and the one or more bisphenols having a hydrocarbylene group containing a triple bond or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and endcapping groups containing a triple bond may be 40 mole percent or less, 30 mole percent or less or about 25 mole percent or less.
  • any of the polymers disclosed herein may be endcapped with a triple bond.
  • the polymers containing the one or more bisphenols having a hydrocarbylene group containing a triple bond or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom may be endcapped with a triple bond.
  • Such endcapping groups may correspond to the formula wherein G is as defined hereinbefore.
  • Compounds useful in endcapping polymers with a triple bond are disclosed in WO 2010/086385, relevant portions incorporated herein by reference.
  • the polymer compositions may contain a mole ratio of monomer units of the one or more biphenols having a direct bond between the phenol groups to the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups sufficient to prepare compositions that exhibits good flame retardant properties including the UL94 flame retardancy, charring properties and antidrip properties.
  • the phenol groups in the polycarbonate polymers described herein may have no substituents on the aromatic rings or substituents on the aromatic rings may comprise C 1.12 alkyl or a halogen. Such phenol groups may have no substituents on the aromatic rings or substituents on the aromatic rings may comprise a methyl or chlorine and/or bromine. Such phenol groups may have no substituents on the aromatic rings.
  • polycarbonates are affected, for example, by the reaction of diphenols with carbonic acid halides, preferably phosgene, and/or with aromatic dicarboxylic acid dihalides, preferably benzenedicarboxylic acid dihalides, by the phase boundary method (often referred to as interfacial polymerization) or melt polymerization, optionally with the use of chain terminators, e.g., monophenols, and optionally with the use of trifunctional branching agents or branching agents with a functionality higher than three, for example triphenols or tetraphenols.
  • phase boundary method often referred to as interfacial polymerization
  • melt polymerization optionally with the use of chain terminators, e.g., monophenols, and optionally with the use of trifunctional branching agents or branching agents with a functionality higher than three, for example triphenols or tetraphenols.
  • Diphenols useful to produce the aromatic polycarbonates and/or aromatic polyester carbonates may correspond to formula I wherein A denotes a single bond, a C 1-5 alkylene, a C 2-5 alkylidene, a C 5-6 cycloalkylidene, -O-,
  • B in each case is independently hydrogen, a C 1-12 alkyl, preferably methyl, or a halogen, preferably chlorine and/or bromine; x in each case is mutually independently 0, 1 , or 2; p is 0 or 1 ;
  • R c and R d are mutually independent of each other and are individually selectable for each X 1 and are hydrogen or a C i_ 6 alkyl, preferably hydrogen, methyl or ethyl;
  • X 1 denotes carbon; and m denotes an integer from 4 to 7, preferably 4 or 5, with the proviso that R c and R d simultaneously denote an alkyl on at least one X 1 atom.
  • Exemplary diphenols are hydroquinone, resorcinol, dihydroxybiphenyls, bis (hydroxyphenyl)-C 1.5 alkanes, bis(hydroxyphenyl)-C 5-6 cycloalkanes, bis(hydroxyl-phenyl) ethers, bis(hydroxyphenyl)sulfoxides, bis(hydroxyphenyl)ketones, bis(hydroxyl-phenyl) sulfones and 4,4”-bis(hydroxyphenyl)diisopropylbenzenes, as well as derivatives thereof which have brominated and/or chlorinated nuclei.
  • Diphenols which are particularly preferred are 4,4'-di hydroxybiphenyl, bisphenol A, 2,4-bis(4-hydroxyphenyl)-2-methyl-butane, 1 ,1-bis (4-hydroxy phenyl)-cyclohexane, 1 ,1-bis(4-hydroxyphenyl)-3,3,5-trimethyl-cyclohexane, 4,4-dihydroxydi phenyl sulfide and 4,4-dihydroxydiphenyl sulfone, as well as di- and tetra-brominated or chlorinated derivatives thereof, such as 2,2-bis(3-chloro-4-hydroxy-phenyl)propane, 2,2-bis-(3,5- dichloro-4-hydroxyphenyl)propane or 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane.
  • 2, 2-bis-(4- hydroxyphenyl) propane (bisphenol A) is particularly preferred.
  • the diphenols can be used individually or as arbitrary mixtures.
  • the diphenols are known in the literature or can be obtained by methods known in the literature.
  • exemplary polycarbonates include copolycarbonates of bisphenol A with up to 15 mole percent, with respect to the molar sums of the diphenols, of other diphenols which are disclosed, such as 2 ,2-bis(3,5- dibromo-4-hydroxyphenyl)-propane.
  • Exemplary chain terminators for the production of the polycarbonates include phenolic compounds, exemplary phenolic compounds include phenol, p-chlorophenol, p-tert-butylphenol, 4-(1 ,3-dimethyl-butyl)-phenol and 2,4,6-tribromophenol; long chain alkyl phenols, such as monoalkylphenols or dialkylphenols which contain a total of 8 to 20 carbon atoms in their alkyl substituents, exemplary are 3,5-di-tert-butyl-phenol, p-iso-octylphenol, p-tert-octylphenol, p- dodecylphenol, 2-(3,5-dimethylheptyl)-phenol and 4-(3,5-dimethylheptyl)-phenol.
  • phenolic compounds include phenol, p-chlorophenol, p-tert-butylphenol, 4-(1 ,3-dimethyl-butyl)-phenol and 2,
  • the amount of chain terminators used may be about 0.1 mole percent or greater based on the molar sum of the diphenols used in each case.
  • the amount of chain terminators used may be about 10 mole percent or less based on the molar sum of the diphenols used in each case.
  • the polycarbonates can be branched, for example by the incorporation of about 0.05 to about 2.0 mole percent, with respect to the sum of the diphenols used, of trifunctional compounds or of compounds with a functionality higher than three, for example those which contain four or more phenolic groups.
  • Branched polycarbonates useful for the compositions disclosed can be prepared by known techniques, for example several methods are disclosed in USP 3,028,365; 4,529,791 ; and 4,677,162; which are hereby incorporated by reference in their entirety.
  • Exemplary branching agents include tri- or multi-functional carboxylic acid chlorides, such as trimesic acid trichloride, cyanuric acid trichloride, 3,3'-,4,4'-benzophenone tetracarboxylic acid tetra chloride, 1 ,4,5,8-naphthalene-tetracarboxylic acid tetrachloride or pyromellitic acid tetra chloride, in amounts of about 0.01 to about 1 .0 mole percent (with respect to the dicarboxylic acid dichlorides used) or tri- or multi-functional phenols such as phloroglucinol, 4,6-dimethyl-2,4,6- tris(4-hydroxyphenyl)-2-heptene, 4,4-dimethyl-2,4,6-tris (4-hydroxy phenyl) heptane, 1 ,3,5-tris(4- hydroxyphenyl)-benzene, 1 ,1 ,1-tris
  • Copolycarbonates may be prepared by known processes. For example, about 1 to about 25 parts by weight, about 2.5 to about 25 parts by weight (with respect to the total amount of diphenols to be used) of polydiorganosiloxanes comprising hydroxy-aryloxy terminal groups can also be used. These are known (see, USP 3,419,634) or can be produced by methods known in the literature.
  • the ester forming monomers may be utilized in the polycarbonate containing polymer preparation process. Exemplary ester forming monomers include dicarboxylic acid halides and hydroxycarboxylic acids.
  • the aromatic dicarboxylic acid dihalides used for the production of the aromatic polyester carbonates may be the diacid dichlorides of isophthalic acid, terephthalic acid, diphenyl ether-4,4'-dicarboxylic acid and naphthalene-2,6-dicarboxylic acid. Mixtures of the diacid dichlorides of isophthalic acid and terephthalic in a ratio from about 1 :20 to about 20:1 may be used.
  • a carbonic acid halide, such as phosgene may be used in conjunction as a difunctional acid derivative during the production of the polyester carbonates.
  • the aromatic polyester carbonates may also contain incorporated hydroxycarboxylic acids.
  • the polyester carbonates may be either linear and/or may be branched.
  • exemplary chain terminators include chlorocarboxylic acid esters, as well as the acid chlorides of aromatic monocarboxylic acids which may optionally be substituted by C 1.22 alkyl groups, or by halogen atoms, and also may include aliphatic C 2-22 monocarboxylic acid chlorides.
  • the amount of chain terminator may be about 0.1 to about 10 mole percent, with respect to the moles of diphenols in the case of phenolic chain terminators and with respect to the moles of dicarboxylic acid dichlorides in the case of monocarboxylic acid chloride chain terminators.
  • the polycarbonates or copolymers containing carbonate units may be derived from recycled materials, such as post-consumer recycled materials.
  • the composition may contain up to 90 percent by weight of the composition recycled polycarbonates, such as post-consumer recycled materials, about 85 percent by weight or less based on the composition or about 80 percent by weight or less.
  • the composition may contain about 30 percent by weight or more of recycled polycarbonate based on the weight of the composition, about 50 percent or more, or about 75 percent by weight or more.
  • the recycled material may be linear, branched or a mixture thereof.
  • the recycled material may be branched.
  • the recycled material may be in flake form.
  • the recycled material may be recycled from bottles or other structures wherein the used structures are shredded into flake form.
  • the recycled material can be formed into other structures such as pellets.
  • the use of the recycled material in pellet form is the most efficient way to utilize the material.
  • the recycled polycarbonates or copolymers containing carbonate units may contain impurities such as polyesters, for instance 0.1 to 1.0 or 0.1 to 0.25 percent by weight based on the recycled polycarbonates or copolymers containing carbonate units.
  • the composition may contain virgin polycarbonates or copolymers containing carbonate units in an amount of about 5 percent by weight or greater based on the composition, about 10 percent by weight or greater, about 20 percent by weight or greater, about 30 percent by weight or greater or about 40 percent by weight or greater.
  • the composition may contain virgin polycarbonates or copolymers containing carbonate units in an amount of 100 percent by weight or less based on the composition, about 90 percent by weight or less, about 60 percent by weight or less or about 50 percent by weight or less.
  • the one or more polymers containing carbonate monomer units can comprise polycarbonates, co-polycarbonates or blends of polycarbonates and co-polycarbonates.
  • the polycarbonates and/or co-polycarbonates may exhibit a weight average molecular weight sufficient to provide the desired properties to articles prepared from the polycarbonates and/or co-polycarbonates.
  • the polycarbonates and/or co-polycarbonates may have a weight average molecular weights of about 5,000 or greater, about 15,000 or greater or about 20,000 or greater.
  • the polycarbonates and/or co-polycarbonates may have a weight average molecular weight of about 60, 000 or less, about 40,000 or less, about 35,000 or less, or about 30,000 or less.
  • polycarbonate and/or co-polycarbonate “molecular weight” herein refer to weight average molecular weights (Mw) determined by gel permeation chromatography (GPC) using laser scattering techniques with a bisphenol A polycarbonate standard and is given in units of grams per mole (g/mole).
  • the polycarbonates and/or copolymers used to prepare the compositions disclosed may have melt flow rates which provide the desired processing properties.
  • the melt flow rates may be about 1 or greater, about 5 or greater, about 10 or greater or about 15 or greater.
  • the melt flow rates may be about 70 or less, about 30 or less, about 28 or less, about 20 or less, or about 15 or less.
  • a mixture of polycarbonates and/or copolymers containing carbonate units with differing melt flow rates may be used to provide a composite melt flow rate to enhance processing of the compositions disclosed.
  • the mixture of polycarbonates and/or copolymers containing carbonate units having different melt flow rates may contain polycarbonates and/or copolymers containing carbonate units having low melt flow rates and polycarbonates and/or copolymers containing carbonate units having high melt flow rates.
  • Melt flow rates are determined by measuring the grams of a material which passes through a capillary having a diameter of 25.4 mm in a ten-minute period at 300 ° C under a load of 1 .2, kilograms.
  • the melt flow rates of the disclosed compositions may be about 1 gram/10 minutes or greater, about 3 grams/10 minutes or greater, about 5 grams/10 minutes or greater, 10 grams/10 minutes or greater or about 15 grams/10 minutes or greater.
  • the melt flow rates of the disclosed compositions may be about 70 grams/10 minutes or less, about 30 grams/10 minutes or less, about 28 grams/10 minutes or less, about 22 grams/10 minutes or less, about 20 grams/10 minutes or less or about 10 grams/10 minutes or less.
  • the melt flow rates of the disclosed compositions may be from about 3 grams/10 minutes
  • the test protocol is based on ASTM D1238.
  • the plastometer used in the method may have a capillary diameter of 9.5504 mm and bore die size of 2.095 mm.
  • the polycarbonates may be linear, branched or a mixture thereof.
  • the polycarbonates may be mixtures of linear and branched polycarbonates.
  • the presence of branched polycarbonates may positively impact the flame retardant properties of the disclosed compositions.
  • the amount of branched polycarbonates may be any amount which positively impacts the properties of the composition including the flame retardant properties and mechanical properties.
  • the amount of the branched polycarbonates and/or copolymers containing carbonate units may be about 0 percent by weight or greater based on the weight of the composition containing polycarbonates and/or copolymers containing carbonate units, 5 percent by weight or greater, about 10 percent by weight or greater, 20 percent by weight or greater, 30 percent by weight or greater, 60 percent by weight or greater, 80 percent by weight or greater or 90 percent by weight or greater.
  • the amount of the branched polycarbonates and/or copolymers containing carbonate units may be about may be about 99 percent by weight or less based on the weight of the composition containing polycarbonates and/or copolymers containing carbonate units, 80 percent by weight or less or about 70 percent by weight or less, 40 percent by weight or less, 20 percent by weight or less or about 15 percent by weight or less.
  • the amount of the linear polycarbonates and/or copolymers containing carbonate units may be about 0 percent by weight or greater based on the weight of the composition containing polycarbonates and/or copolymers containing carbonate units, 5 percent by weight or greater or about 10 percent by weight or greater.
  • the amount of the linear polycarbonates and/or copolymers containing carbonate units may be about may be about 99 percent by weight or less based on the weight of the composition containing polycarbonates and/or copolymers containing carbonate units, 80 percent by weight or less or about 70 percent by weight or less, 40 percent by weight or less, 20 percent by weight or less or about 15 percent by weight or less.
  • the compositions may contain one or more organometallic salts which function as charring salts.
  • a charring salt is any compound which assist in the retention of the original shape of the plastic article by the formation of char from the compound. The char forms a crust of non-flammable material, reducing the melting and dripping of the compound in which the charring salt resides.
  • Any organometallic salt which functions as a charring salt may be used, with the proviso that the charring salt does not contain a halogen, such as fluorine.
  • the one or more organometallic salts may be one or more salts of aromatic sulfur compounds.
  • the one or more organometallic salts may be one or more salts of aromatic sulfonates.
  • the one or more salts of aromatic sulfur compounds may include one or more salt of an alkali metal, an alkaline earth metal or both.
  • the one or more salts aromatic sulfur compounds may include a potassium salt, a sodium salt, a magnesium salt, a calcium salt, or any combination thereof.
  • the one or more salts of aromatic sulfur compounds may include one or more sodium or potassium salts.
  • the one or more salts of aromatic sulfur compounds may be a sulfonate.
  • the sulfur-containing salt may include one or more carbon containing groups. The number of carbon atoms in the sulfur- containing salt may be about 15 or less, about 13 or less, about 7 or less, or about 5 or less.
  • the number of carbon atoms in the sulfur-containing salt may be 1 or more, 2 or more, 3 or more, or 4 or more.
  • the carbon containing group may be acyclic or aromatic.
  • the sulfur-containing salt may include or consist substantially of one or more sodium p-toluenesulfonate or potassium diphenylsulfone sulfonate.
  • the organometallic salts aromatic sulfur compounds may be present in an amount to improve the flame retardancy of the compositions.
  • the organometallic salts may be present in an amount of about 0.01 percent by weight or greater of the composition or about 0.05 percent by weight or greater or about 0.1 percent by weight or greater.
  • the organometallic salts may be present in an amount of about 2.0 percent by weight or less of the composition, about 1.0 percent by weight or less, about 0.5 percent by weight or less, about 0.4 percent by weight or less or about 0.25 percent by weight or less.
  • compositions disclosed may contain one or more inorganic particles. Any inorganic particles which enhance the flame retardant and mechanical properties of the composition may be utilized.
  • the one or more inorganic particles may be one or more carbon based particulates, metal oxides and metalloid oxides. Exemplary metal or metalloid oxides include group 3 or 4 metal or metalloid oxides and mixtures thereof which may be synthetic or naturally occurring. Exemplary metal or metalloid oxides include TiO2, MgO, SiO2, Fe2Os, AI2O3 and the like. Exemplary metal or metalloid oxides include TiO 2 , MgO and SiO 2 .
  • the one or more metal or metalloid oxides may be a mixture of metal and/or metalloid oxides, such as talc which contains MgO and SiO 2 , mica, which contains silica and oxygen, and wollastonite calcium silicates.
  • the one or more carbon based particulates may be any particulate carbon materials which improve the flame retardancy of the compositions disclosed herein. Exemplary carbon based particulates may be carbon black or carbon nanotubes.
  • the one or more carbon compounds, metals or metalloid oxides may be present in a sufficient amount to enhance the flame retardancy and mechanical properties of the composition.
  • the one or more carbon based particulates, metal or metalloid oxides may be present in an amount sufficient to provide a flame retardancy rating of V0@1 .5 mm.
  • the one or more carbon based particulates, metal or metalloid oxides may be present in an amount of about 0 weight percent by weight or greater based on the weight of the composition, about 0.2 percent by weight or greater, about 0.3 percent by weight or greater or about 0.5 percent by weight or greater.
  • the one or more carbon based particulates, metal or metal oxides may be present in an amount of about 10 weight percent by weight or less based on the weight of the composition, about 5 percent by weight or less, about 3 percent by weight or less or about 2 percent by weight or less.
  • the one or more carbon based particulates, metal or metal oxides may be nanoparticles.
  • the particle size may be any particle size that which enhances the flame retardancy rating of the compositions.
  • the particle size may be about 0.005 micrometers or more, about 0.01 micrometers or more, about 0.2 micrometers or more or about 0.35 micrometers or more.
  • the particle size may be about 2.0 micrometers or less or about 1.0 micrometers or less.
  • the particle size may be determined using the laser diffraction technique described in ISO13322. The particle size determined is the average diameter.
  • compositions disclosed herein may contain one or more buffer compounds, buffer system. Any buffer system which enhances the stability of the molecular weight of the polycarbonate may be utilized.
  • a buffer system as described herewith may be any compound that donates protons (i.e., H + or hydronium ion), accepts protons (i.e., H + or hydronium ion), or both.
  • the buffer system may comprise a weak acid and a conjugate base.
  • the buffer system may resist pH changes upon the addition of basic or acidic components.
  • the buffer system may be characterized based on the total number of protons (i.e., H + or hydronium ion), hydroxyl groups (i.e., hydroxide or OH ), or both.
  • the buffer system may include one or more buffer compounds that are monoprotic, diprotic, triprotic, or polyprotic.
  • the buffer system may proportionally stabilize polycarbonates based on the total amount of buffer system present based on the total weight of the composition.
  • a buffer system as described herewith includes one or more buffers that has an acidic and basic functionality such that the pH of the composition may be directed to about neutral.
  • the buffer system may include one or more buffer compounds, two or more buffer compounds, three or more buffer compounds, or a plurality of buffer compounds.
  • the buffer system may comprise a single compound.
  • the buffer system may comprise a pair of compounds.
  • the buffer system may include an inorganic compound, an organic compound, or both.
  • the buffer system may include a counterion.
  • the buffer system is a present in a concentration (i.e., percentage by weight of the total composition) sufficient to facilitate improved molecular weight stability of polycarbonate.
  • the buffers system may include a buffer compound that is an inorganic compound or organic compound that balances the pH of the composition such that the optimal copolymerization and compounding is achieved.
  • Inorganic compounds may include compounds that are free of saturated carbons (i.e., free of C-H bonds).
  • the inorganic compounds may include carbon atoms that do not include hydrogen bonds.
  • Organic compounds may include compounds that contain saturated carbons (i.e. , contains C-H bonds).
  • the buffer compounds may include acetates, sulfonates, phosphates, ammonia, formates, or any combination thereof.
  • the buffer system may include buffer compounds that are aromatic or aliphatic.
  • the buffer system may include pairs of buffer compounds that are weak acids and conjugate bases.
  • the buffer compounds may be chosen based on a pKa that is about neutral.
  • the buffer compounds may control the pH of water to about neutral.
  • the buffer system may include a Good’s buffer.
  • Organic compounds may include 2-(N-morpholino)ethanesulfonic acid (MES), 2-[Bis(2- hydroxyethyl)amino]-2-(hydroxymethyl) propane-1 , 3-diol (Bis-Tris Methane), 2-[(2-amino-2- oxoethyl)-(carboxy methyl) mino]acetic acid (ADA), N-(2-Acetamido)-2-aminoethanesulfonic acid (ACES), piperazine-N,N'-bis(2-ethane sulfonic acid) (PIPES), 2-Hydroxy-3-morpholino propanesulfonic acid (MOPSO), 1 ,3-bis(tris(hydroxymethyl) methylamino)propane (Bis-6-Tris Propane), N-N-Bis(2-hydroxyethyl)-2-aminoethane sufionic acid (BES), MOPS, 2-[[1 ,3-dihydroxy
  • the buffer system may comprise one or more alkali metal phosphates. Any alkali metal phosphates which enhance the thermal stability of the compositions may be used.
  • the alkali metal phosphates may be sodium or potassium metal phosphates.
  • Exemplary alkali metal phosphates may be one or more of distearyl pentaerythritol diphosphate, mono or dihydrogen phosphate and mono-, di-, or trihydrogen phosphate compounds.
  • Exemplary alkali metal phos-phates may be one or more of mono-, di-, or trihydrogen phosphate compounds.
  • the alkali metal phosphate may be sodium dihydrogen phosphate.
  • the alkali metal phosphates may be used in any amount which enhances the thermal stability of the compositions.
  • the alkali metal phosphates may be used in any amount of about 0 percent by weight or greater based on the weight of the composition, about 0.01 percent by weight or greater, about 0.02 percent by weight or greater or about 0.03 percent by weight or greater.
  • the alkali metal phosphates may be used in any amount of about 1.0 percent by weight or less based on the weight of the composition, about 0.5 percent by weight or less, about 0.2 percent by weight or less or about 0.1 percent by weight or less.
  • the composition may contain one or more impact modifiers.
  • impact modifiers and rubbers are used interchangeably.
  • Various impact modifiers may be used in the compositions disclosed; such as diene rubbers, ethylene propylene rubbers, ethylene propylene diene (EPDM) rubbers, ethylene copolymer rubbers, acrylate rubbers, polyisoprene rubbers, silicon rubbers, silicon-acrylate rubbers, poly urethanes, thermoplastic elastomers, halogen containing rubbers, and mixtures thereof.
  • inter-polymers of rubber-forming monomers with other copolymerizable monomers are also suitable.
  • the rubbers may be present in the composition in sufficient amount to provide the desired impact properties to the composition. Desired impact properties include increased notched izod, charpy, gardner, tensile, falling dart.
  • the rubbers may be diene rubbers such as polybutadiene, polyisoprene, polypiperylene, polychloroprene, and the like or mixtures of diene rubbers, that is, any rubbery polymers of one or more conjugated 1 ,3-dienes, such as 1 ,3-butadiene.
  • diene rubbers include homopolymers of 1 ,3-butadiene and copolymers of 1 ,3-butadiene with one or more copolymerizable monomers, such as vinylidene substituted aromatic (styrene).
  • the diene rubber may be the homopolymer of 1 ,3-butadiene.
  • Exemplary copolymers of 1 ,3-butadiene are block or tapered block rubbers of at least about 30 weight percent 1 ,3-butadiene, from about 50 weight percent, from about 70 weight percent, or from about 90 weight percent 1 ,3-butadiene and up to about 70 weight percent vinylidene substituted aromatic monomer, up to about 50 weight percent, up to about 30 weight percent, or up to about 10 weight percent vinylidene substituted aromatic monomer, weights based on the weight of the 1 ,3-butadiene copolymer.
  • the impact modifiers employed may be those polymers and copolymers which exhibit a second order transition temperature, sometimes referred to as the glass transition temperature (Tg), for the diene fragment which is not higher than 0° C or not higher than -20° C. as determined using conventional techniques, for example ASTM Test Method D 746-52 T.
  • Tg glass transition temperature
  • the diene rubber may have a cis content equal to or less than 99 percent or less than 97 percent.
  • the cis content of the diene rubber may be equal to or greater than 20 percent or greater than 37 percent wherein the cis weight percent is based on the weight of the diene rubber.
  • the rubber may be a 1 ,3- butadiene rubber having at least about 1 weight percent 1 ,2-vinyl or at least about 7 weight percent 1 ,2-vinyl based on the weight of the 1 ,3-butadiene rubber.
  • the 1 ,3-butadiene rubber may have less than or equal to about 30 weight percent 1 ,2-vinyl or less than or equal to about 13 weight percent 1 ,2-vinyl based on the weight of the 1 ,3-butadiene rubber.
  • the diene rubber may have a weight average molecular weight of at least about 100 kilogram per mole (kg/mole) or a weight average molecular weight of at least about a 300 kg/mole.
  • the diene rubber may have a weight-average molecular weight equal to or less than about 900 kg/mole or a weight average molecular weight equal to or less than 600 kg/mole.
  • the diene rubber having a solution viscosity of at least 10 centiStokes (cSt) (10 percent (%) solution in styrene) or a solution viscosity of about 30 cSt.
  • the diene rubber may have a solution viscosity equal to or less than about 500 cSt or equal to or less than about 400 cSt.
  • the rubber, with graft and/or occluded polymers if present, is dispersed in the continuous matrix phase as discrete particles.
  • the rubber particles may comprise a range of sizes having a mono-modal, bimodal, or multimodal distribution.
  • the average particle size of a rubber particle will, refer to the volume average diameter, the volume average diameter of a group of particles may be the same as the weight average.
  • the average particle diameter measurement generally includes the polymer grafted to the rubber particles and occlusions of polymer within the particles. Unless otherwise specified, the rubber particle sizes disclosed and claimed herein are determined on a Coulter Multisizer II or II e with the ACCUCOMPTM Software Version 2.01.
  • the average particle size of the rubber particles may be equal to or greater than about 0.05 micrometers (microns) (pm), equal to or greater than about 0.1 pm, and equal to or greater than about 0.5 pm.
  • the average particle size of the rubber particles may be equal to or less than about 10 pm, equal to or less than about 5 pm, or equal to or less than about 4 pm.
  • the impact modifier may be butadiene- or styrene-butadiene rubber-based and methyl methacrylate-styrene-grafted impact modifiers having a core-shell structure (MBS), siloxaneacrylate rubbers having a core-shell structure, acrylate rubber-based core-shell impact modifiers, and the like.
  • MFS core-shell structure
  • siloxaneacrylate rubbers having a core-shell structure acrylate rubber-based core-shell impact modifiers, and the like.
  • the butadiene- or styrene-butadiene rubber-based core-shell impact modifiers are butadiene- or styrene-butadiene rubber-based impact modifiers grafted with methyl methacrylate or methyl methacrylate-styrene copolymers, e.g., Kane Ace M732 available from Kaneka Japan and ParaloidTM EXL2650J, EXL2690 and EXL2691 J available from Dow Chemical, and the like.
  • Siloxane-acrylate rubbers having a core-shell structure may be produced from alkyl methacrylates and/or alkyl acrylates, crosslinkers, and grafting agents.
  • a monomer having more than one polymerizable double bond can be used as the crosslinker for the polyalkyl(meth)acrylate-rubber component of siloxane-acrylate rubber.
  • the crosslinking monomers are esters of unsaturated mono-carboxylic acids having 3 to 8 carbon atoms and unsaturated monohydric alcohols having 3 to 12 carbon atoms or saturated polyols having 2 to 4 OH-groups and 2 to 20 carbon atoms, e.g., ethylene glycol dimethacrylate, propanediol dimethacrylate, 1 ,3-butanediol dimethacrylate, and 1 ,4-butanediol dimethacrylate.
  • Such crosslinkers may be used alone or as mixtures of at least two crosslinkers.
  • Exemplary grafting agents are allyl methacrylate, triallylcyanurate, triallyl isocyanurate or mixtures thereof.
  • the allyl methacrylate may further be used as the crosslinker.
  • Such grafting agents may be used alone or as mixtures of at least two grafting agents.
  • the crosslinker and grafting agent may be present in an amount of from about 0.1 wt.-% to about 20 wt.-% based on the total weight of the polyalkyl(meth)acrylate-rubber component of siloxane- acrylate rubber.
  • Exemplary siloxane-acrylate rubbers include, for example, Metablen S-2100, S- 2001 , S-2006 and the like available from Mitsubishi Rayon. Kane Ace MR03 and the like available from Kaneka.
  • the compositions may comprise the siloxane-acrylate rubber impact modifier preferably in an amount of from 1 wt.-% to 8 wt.-%, and more preferably from 1 wt.-% to 6 wt.-%, particularly preferred from 2.0 to 5.0 wt.-% of the total weight of the composition.
  • Exemplary acrylate rubber-based core-shell impact modifiers are acrylate rubber-based impact modifiers grafted with methyl methacrylate, including ParaloidTM EXL2311 , EXL2313, EXL2315, EXL2300, EXL2330 and EXL2390 available from Dow; and Durastrength® 410, 440 and 480 available from Arkema.
  • the impact modifier may be siloxane-acrylate core shell rubber having a siloxane core wherein the siloxane core is from about 20 to about 70 percent by weight of the core shell rubber.
  • compositions disclosed herein contain impact modifiers in an amount of 0 percent by weight of the compositions or greater, about 0.5 percent by or greater, about 1.0 percent by weight or greater or about 2.0 percent by weight or greater based on the weight of the composition.
  • the compositions disclosed herein contain impact modifiers in an amount of about 8 percent by weight of the compositions or less, about 6 percent by weight or less, about 6 percent by weight or less, about 5 percent by weight or less or about 3.0 percent by weight or less.
  • Impact modifiers may impact the effectiveness of the flame retardants and the amount and choice of the flame retardant compounds may need to be adjusted upward to provide the desired flame retardant properties.
  • the compositions may contain one or more flame retardants commonly used in polycarbonate compositions.
  • the flame retardants may be any flame retardant known for use in polycarbonate-based compositions which provide flame retardant properties, and which do not negatively impact the impact, heat resistance, flexural modulus, bending strength, haze and transparency of the composition. Flame retardants may be used in a sufficient amount to meet the flame retardancy requirements for the final use and in an amount that does not deleteriously impact the properties of articles prepared from the compositions.
  • the compositions may contain one or more halogenated flame retardants commonly used in polycarbonate compositions.
  • Exemplary flame retardants include brominated polycarbonates, such as tetrabromobisphenol A polycarbonate oligomer, polybromophenyl ether, brominated BPA polyepoxide, brominated imides, halogenated polyacrylates, such as poly (haloaryl acryl-ate), poly(haloaryl methacrylate), brominated polystyrenes such as polydibromostyrene and polytribromostyrene, decabromobiphenyl ethane, tetrabromobiphenyl, brominated alpha, omega-alkylene-bis- phthalimides.such as.
  • brominated polycarbonates such as tetrabromobisphenol A polycarbonate oligomer, polybromophenyl ether, brominated BPA polyepoxide, brominated imides, halogenated polyacrylates, such as poly (haloaryl acryl-ate), poly(haloaryl methacrylate), bromin
  • Mixtures of halogenated flame retardants may be utilized in the compositions.
  • Exemplary halogenated flame retardants include brominated polyacrylates, brominated polystyrenes and tetrabromobisphenol A polycarbonate oligomers.
  • the compositions may contain one or more nonhalogenated flame retardants commonly used in polycarbonate compositions. Non-halogenated means that there are no halogen atoms contained in the flame retardant. The use of nonhalogenated flame retardants means that no halogens are released during combustion of the compositions containing non-halogenated flame retardants.
  • Exemplary nonhalogenated flame retardants include phosphorous containing compounds, such as oligomeric phosphates, poly(block-phosphonato-esters), and/or a poly(block-phosphonato-carbonates) see USP 7,645,850 which is incorporated in its entirety.
  • Exemplary oligomeric phosphates include bisphenol-A bis(diphenyl phosphate) (BAPP).
  • Exemplary additional fire retardants include 1 , 3-phenylenetetrakis (2, 6-dimethylphenyl) ester (Daihachi PX-200).
  • the one or more non-halogenated flame retardants may be one or more phosphazenes.
  • the phosphazenes may comprise more than one phosphazene unit.
  • the phosphazene may be a linear structure containing one or more phosphazene units or a cyclic structure containing structure containing one or more phos phazene units.
  • the phosphorous atoms on the phosphazene structure may have bonded thereto one or more hydrocarbyloxy structures.
  • the hydro-carbyloxy groups may be alkoxy, aryloxy, alkyl substituted aryloxy, alkoxy substituted aryloxy or halo substituted aryloxy.
  • the hydrocarbyloxy groups may be aryloxy or alkyl substituted aryloxy.
  • the hydrocarbyloxy groups may be phenoxyoxy or alkyl substituted phenoxy.
  • the alkyl groups may be C -MO alkyl, C 1.3 alkyl or methyl or ethyl.
  • the cyclic phosphazene compounds may contain 1 or more phosphazene units or 3 or more phosphazene units.
  • the cyclic phosphazene compounds may contain 25 or less phosphazene units, 10 or less phosphazene units or 5 or less phosphazene units.
  • the linear phosphazene compounds may contain 1 or more phosphazene units, 3 or more phosphazene units, 5 or more phosphazene units or 6 or more phosphazene units.
  • the linear phosphazene compounds may contain 10,000 or less phosphazene units, 1 ,000 or less phosphazene units, 100 or less phosphazene units, or 25 or less phosphazene units.
  • Exemplary cyclic phosphazenes include phenoxy cyclotriphosphazene, octaphenoxy cyclotetraphos- phazene, and decaphenoxy cyclopentaphosphazene.
  • Cyclic phosphazenes may be obtained by allowing ammonium chloride and phosphorus pentachloride to react at 120 to 130°C to obtain a mixture containing cyclic and straight chain chlorophosphazenes, extracting cyclic chlorophosphazenes such as hexachlorocyclotri phosphazene, octa-chloro cyclotetraphosphazene, and decachloro cyclopentaphosphazene, and then sub-stituting it with a phenoxy group.
  • Exemplary linear phosphazenes include compounds obtained by subjecting hexachloro cyclotriphosphazene, obtained by the above-described method, to ring-opening polymerization at 220 to 250°C, and then substituting thus obtained chainlike dichlorophosphazene having a degree of polymerization of 3 to 10,000 (or as described before) with phenoxy groups.
  • the phosphazene compounds may be crosslinked.
  • the phosphazene compounds may be crosslinked by a bisphenol compound such as a 4,4'-diphenylene group, such as a 4,4'-sulfonyldiphenylene (bisphenol S residue), 2,2-(4 ,4'- diphenylene), isopropylidene group, 4,4'-oxydiphenylene group, and 4,4'-thiodiphenylene group.
  • a bisphenol compound such as a 4,4'-diphenylene group, such as a 4,4'-sulfonyldiphenylene (bisphenol S residue), 2,2-(4 ,4'- diphenylene), isopropylidene group, 4,4'-oxydiphenylene group, and 4,4'-thiodiphenylene group.
  • the phenylene group content of the crosslinked phenoxyphosphazene compound is generally 50 to 99.9 weight percent or 70 to 90 weight percent.
  • the crosslinked phenoxyphosphazene compound may not have any free hydroxy
  • the one or more flame retardants may be present in an amount of about 0.1 percent by weight or greater based on the weight of the composition containing polycarbonates and/or copolymers containing carbonate units, about 1 percent by weight or greater or about 5 percent by weight or greater.
  • the one or more flame retardants may be present in an amount of about 30 percent by weight or less based on the weight of the composition, about 20 percent by weight or less or about 10 percent by weight or less.
  • the disclosed compositions contain one of more antioxidants.
  • Antioxidants may be introduced into the compositions from ingredients utilized, such as the impact modifiers.
  • the antioxidants may be added to the compositions separately.
  • the antioxidants may be one or more of phenol, phosphorous, hydroquinone and alkylated hydroquinone, tocopherol, O- and N-benzyl compound, alkylidenebisphenol, hydroxy benzylated malonate, aromatic hydroxybenzyl compound, triazine compound, benzyl phosphonate, acylaminophenol, esters and amides of propionic acid, ascorbic acid, or aminic based antioxidants.
  • the antioxidant may be one or more of phenol, phosphorous, hydroquinone and alkylated hydroquinone, tocopherol, O- and N-benzyl compound, alkylidenebisphenol, hydroxybenzylated malonate, aromatic hydroxybenzyl compound, triazine compound, benzylphosphonate, acylaminophenol, esters and amides of propionic acid, ascorbic acid, or aminic based antioxidants.
  • the antioxidants may be one or more of phenol based compounds and or phosphite (phosphorous) based antioxidants.
  • Phenol based antioxidants include 2,6-di-tert-butyl-4-methylphenol; 2,6-diphenyl-4- methoxyphenol; 2,2'-methylenebis (6-tert-butyl-4-methylphenol); 2,2'-methylenebis(6-tert-butyl-4- methylphenol); 2,2'-methylene bis [4-methyl-6-(a-methylcyclohexyl)phenol]; 1 ,1-bis (5-tert-butyl- 4-hdyroxy-2-methyl phenyl) butane; 2,2'-methylenebis(4-methyl-6-cyclohexyl phenol); 2,2'- methylenebis(4-methyl-6-nonylphenol); 1 ,1 ,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl) butane; 2,2-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercap
  • Hydroquinone and alkylated hydroquinone-based antioxidants include 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert- amylhydroquinone, 2,6-di phenyl 4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di- tert-butyl-4-hydroxy anisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis (3,5-di-tert-butyl-4-hydroxyphenyl) adipate.
  • Tocopherol based antioxidants include a-tocopherol, p-tocopherol, y-tocopherol, b-tocopherol and mixtures thereof (vitamin E).
  • O- and N-benzyl compounds, based antioxidants include for example 3,5,3',5'-tetra-tert-butyl-4,4'- dihydroxydi benzyl ether, tris(3,5-di-tert-butyl-4-hydroxybenzyl) amine.
  • Alkylidenebisphenol, based antioxidants include, 2,2'-methylenebis(6-tert-butyl-4-methyl phenol), 2,2'-methylene bis(6- tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(a-methyl cyclo hexyl) phenol], 2,2'- methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylene bis(6-nonyl-4-methylphenol), 2,2'- methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis (4,6-di-tert-butylphenol), 2,2 -ethylidene bis(6-tert-butyl-4-isobutylphenol), 2,2'-methylene bis[6-(a-methylbenzyl)-4-nonylphenol], 2,2'- methylene bis[6-(a,a-dimethyl
  • Hydroxy benzylated malonate based antioxidants include dioctadecyl-2, 2-bis(3,5-di-tert-butyl-2-hydroxy benzyl)malonate, di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methyl benzyl)malonate, bis[4- (1 ,1 ,3,3-tetramethyl butyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxy benzyl)malonate.
  • Aromatic hydroxybenzyl based antioxidants include 1 ,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6- trimethyl benzene, 1 ,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6- tris (3,5-di-tert-butyl-4-hydroxy benzyl)phenol.
  • Triazine compounds based antioxidants include 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1 ,3,5-triazine, 2-octylmercapto-4,6- bis(3,5-di-tert-butyl -4-hydroxyanilino)-1 ,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4- hydroxy phenoxy)- 1 ,3,5-triazine, 2,4,6-tris-(3,5-di-tert-butyl-4-hydroxyphenoxy)-1 ,2 ,3-triazine,
  • Benzylphos phonates, based antioxidants include dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphos phonate, diethyl-3, 5-di-tert-butyl-4-hydroxybenzylphosphonate, diocta decyl3,5-di-tert-butyl-4-hydroxy benzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.
  • Acylamino phenol based antioxidants include, for example 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5- di-tert-butyl-4-hydroxyphenyl) carbamate.
  • Exemplary antioxidants include esters of D-(3,5-di-tert- butyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols, e.g.
  • antioxidants include esters of p-(5-tert-butyl-4-hydroxy-3- methyl phenyl)propionic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, n- octanol, i-octanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis-(hydroxyethyl) oxamide, 3-thia undecanol, 3- thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha
  • antioxidants include esters of p-(3,5-dicyclohexyl-4-hydroxy phenyl)propionic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, octanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonanediol, ethylene glycol,
  • 1.2-propanediol neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N,N'-bis(hydroxyethyl) oxamide, 3- thiaundecanol, 3-thia pentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1- phospha-2,6,7-trioxabicyclo[2.2.2]octane.
  • antioxidants include esters of 3,5-di-tert- butyl-4-hydroxyphenyl acetic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, octanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl) oxamide, 3-thiaundecanol, 3-thia pentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7- trioxabicyclo[2.2.2]octane.
  • antioxidants include amides of p-(3,5-di-tert-butyl-4- hydroxyphenyl) propionic acid e.g. N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexa methylene diamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxy phenyl propionyl) tri methylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide, N, N'-bis[2-(3-[3,5-di-tert-butyl-4- hydroxyphenyl]propionyloxy)ethyl]oxamide (Naugard® XL-1 , supplied by Uniroyal).
  • antioxidants include N,N'-di-isopropyl-p- phenylenediamine, N,N'-di-sec-butyl-p-phenylene diamine, N,N'-bis(1 ,4-dimethylpentyl)-p- phenylenediamine, N,N'-bis(1-ethyl-3-methylpentyl) -p-phenylene di-amine, N,N'-bis(1- methylheptyl)-p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p- phenylenediamine, N,N'-bis(2-naphthyl)-p-phenylene diamine, N-isopropyl-N'-phenyl-p- phenylenediamine, N-(1 ,3-
  • Phosphoric antioxidants include tetrakis(2,4-di-t-butyl phenyl)-4,4-biphenylene phosphonite, tris(2,4-di-t- butylphenyl) phosphite, 2,2'-methylene bis(4,6-di-t-butylphenyl) octyl phosphite, bis(2,4-di-t-butyl phenyl)pentaerythritol diphosphite, bis(2,6-di-t-butyl-4-methylphenyl)pentaerythritol diphosphite, di(nonylphenyl)pentaerythritol diphosphite, phenyl-bisphenol A-pentaerythritol diphosphite, distearylpentaerythritol diphosphite, dioctylpentaerythrito
  • Exemplary antioxidant additives include, for example, organophosphites such as tris(nonyl phenyl)phosphite, tris(2,4-di-t-butylphenyl)phosphite (e.g., “IRGAFOS 168” or “1-168”), bis(2,4-di-t-butylphenyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite or the like; alkylated monophenols or polyphenols; alkylated reaction products of polyphenols with dienes, such as tetrakis[methylene(3,5-di-tert-butyl-4-hydroxyhydro cinnamate) methane, or the like; butylated reaction products of para-cresol or dicyclopentadiene; alkylated hydroquinones; hydroxylated thiodiphenyl ethers; alkylidene
  • the antioxidants may be present in the compositions and structures formed therefrom in any amount which retards oxidation of the polymers.
  • the antioxidants may be present in an amount based on the weight of the compositions disclosed of about 100 parts per million or greater, about 200 parts per million or greater, about 300 parts per million or greater, about 500 parts per million or greater or about 1000 parts per million or greater.
  • the antioxidants may be present in an amount based on the weight of the compositions disclosed of about 10,000 parts per million or less, about 8,000 parts per million or less or about 6,000 parts per million or less.
  • the compositions may contain mold release agents.
  • Exemplary mold release agents include any mold release agent known in the art and combinations thereof.
  • the mold release agents may be internal mold release agents.
  • the mold release agents may include one or more compatibilizing agents such as are taught in now expired United States patent US5,212,209A which is incorporated herein by reference in its entirety for all purposes.
  • Exemplary classes of mold release agent include aliphatic carboxylic acids; esters of an aliphatic carboxylic acid and an alcohol; aliphatic hydrocarbon compounds having a number average molecular weight of 200 to 15,000; and polysiloxane-based silicone oils.
  • Examples of the aliphatic carboxylic acids include saturated or unsaturated, aliphatic monovalent, divalent, or trivalent carboxylic acids.
  • the aliphatic carboxylic acids also include alicyclic carboxylic acids.
  • the aliphatic carboxylic acids may be C 6 -36 monovalent or divalent carboxylic acids.
  • the aliphatic carboxylic acids may be C 6 - 36 aliphatic saturated monovalent carboxylic acids.
  • Specific examples of such aliphatic carboxylic acids include palmitic acid, stearic acid, caproic acid, capric acid, lauric acid, arachic acid, behenic acid, lignoceric acid, cerotic acid, melissic acid, tetratriacontanoic acid, montanic acid, adipic acid, and azelaic acid.
  • Examples of the aliphatic carboxylic acid in the esters of an aliphatic carboxylic acid and an alcohol include the same aliphatic carboxylic acids as described above.
  • Examples of the alcohol include saturated or unsaturated, monohydric or polyhydric alcohols, which may have a substituent such as a fluorine atom or an aryl group.
  • the alcohols may be monohydric or polyhydric, saturated alcohols having a carbon number of not more than 30.
  • the alcohols may be aliphatic saturated monohydric alcohols and aliphatic saturated polyhydric alcohols having a carbon number of not more than 30.
  • the term “aliphatic” herein is used as a term also including alicyclic compounds.
  • Such alcohols include octanol, decanol, dodecanol, stearyl alcohol, behenyl alcohol, ethylene glycol, diethylene glycol, glycerin, pentaerythritol, 2,2- dihydroxyperfluoropropanol, neopentylene glycol, ditrimethylol propane, and dipentaerythritol.
  • Each of the above esters may be either a pure substance ora mixture of a plurality of compounds.
  • Each of the aliphatic carboxylic acid and the alcohol bound to each other to constitute one ester may be of a single type, or two or more types thereof may be used in an arbitrary combination at arbitrary ratios.
  • ester of the aliphatic carboxylic acid and the alcohol include bees waxes (mixtures containing myricyl palmitate as a major component), stearyl stearate, behenyl behenate, stearyl behenate, glycerin monopalmitate, glycerin monostearate, glycerin distearate, glycerin tristearate, pentaerythritol monopalmitate, pentaerythritol monostearate, pentaerythritol distearate, pentaerythritol tristearate, and pentaerythritol tetrastearate.
  • Examples of the aliphatic hydrocarbons having a number average molecular weight of 200 to 15,000 include liquid paraffins, paraffin waxes, microwaxes, polyethylene waxes, Fischer-Tropsch waxes, and a-olefin oligomers having a carbon number of 3 to 12.
  • the aliphatic hydrocarbons also include alicyclic hydrocarbons. Each of these hydrocarbons may be partially oxidized, the aliphatic hydrocarbons may be paraffin waxes, polyethylene waxes, and partially oxidized polyethylene waxes are preferred. Paraffin waxes and polyethylene waxes are more preferred.
  • the number average molecular weight of the aliphatic hydrocarbon may not more than 5000.
  • polysiloxane-based silicone oils examples include dimethyl silicone oils, methylphenyl silicone oils, and diphenyl silicone oils.
  • a single type of mold release agent described above may be included, or two or more types of mold release agents described above may be included in an arbitrary combination at arbitrary ratios.
  • the amount of the mold release agent is not limited and may be about 0.001 percent by weight or greater based on the composition, about 0.01 percent by weight or greater or about 0.1 percent by weight or greater.
  • the amount of the mold release agent is not limited and may be about 2 percent by weight or less based on the weight of the composition, about 1 percent by weight or less, or about 0.6 percent by weight or less. In cases where the content of the mold release agent is less than the lower limit of this range, the mold-releasing effect may be insufficient, while in cases where the content of the mold release agent exceeds the upper limit of this range, a decrease in the hydrolysis resistance, mold contamination during injection molding, and the like may occur.
  • compositions disclosed herein may include an UV absorber (i.e. , UV stabilizers) that function to stabilize the color of the composition.
  • UV absorbers When UV absorbers are added, the polycarbonatesmay absorb light energy from UV rays as heat. UV absorbers may reduce weathering in polymeric compositions.
  • UV absorbers may include benzotriazoles, hydroxyphenyltriazines, benzophenoses, s-triazines, the like, or any combination thereof. UV absorbers may be present in an amount based on the weight of the composition of about 500 ppm or more, about 1 ,000 ppm or more, or about 1 ,500 ppm or more.
  • UV absorbers may be present based on the weight of the composition of about 10,000 ppm or less, about 8,000 ppm or less, or about 6,000 ppm or less. UV absorbers may be present in an amount of about 500 ppm to about 10,000 ppm.
  • the fillers may be reinforcing fillers, such as fibers having a length to diameter ratio of about 4 or more.
  • the amount of other fillers e.g., non-reinforcing fillers, such as talc, clay, etc.
  • a reinforcing filler may be employed for improving the strength of the composition and/or for reducing the coefficient of linear thermal expansion of the composition.
  • the reinforcing filler may include a glass fiber, a carbon fiber, a metal fiber, or any combination thereof.
  • the composition may optionally include a component which adsorbs volatile organic compounds.
  • the component may be a zeolite, activated carbon, bamboo, charcoal or combinations thereof.
  • compositions may contain one or more additives that are commonly used in compositions of this type.
  • additives include: zinc salts, colorants, stabilizers, adsorbers (e.g., zeolites, activated carbon, bamboo charcoal, etc.), antistatic agents, silicon oils, flow enhancers, etc.
  • Additives and/or adsorbents may be present in the compositions in an amount about 0.01 percent by weight or greater, about 0.1 percent by weight or greater, about 1 percent by weight or greater, about 2 percent by weight or greater, or about 3 percent by weight or greater based on the weight of the compositions.
  • the additives and/or fillers may be present in an amount of about 40 percent by weight or less, about 30 percent by weight or less, about 20 percent by weight or less, about 15 percent by weight or less, about 10 percent by weight or less, about 5 percent by weight or less based on the weight of the composition.
  • the additives and adsorbents may be independently present in amounts up to about 5 weight percent while fillers may be present in amounts up to about 40 weight percent based on the weight of the compositions.
  • compositions disclosed may be produced by mixing the components in a known manner and melt-compounding and/or melt-extruding them at temperatures of from 250°C to 330°C in conventional units such as internal kneaders, extruders and twin-screw extruders.
  • the individual components may be mixed in a known manner both in succession and simultaneously and both at approximately 23°C (room temperature) and at a higher temperature.
  • the mixing may be performed for a time sufficient to form a homogeneous mixture of the components,
  • the mixing time may be about 10 seconds or greater, 20 second or greater of about 30 seconds or greater.
  • the mixing time may be 600 seconds or less.
  • the disclosed compositions may be molded using procedures known in the art.
  • the polycarbonate compositions may be molded into useful shaped articles by a variety of means such as injection molding, overmolding, extrusion, rotational molding, blow molding and thermoforming to form various molded articles.
  • Such articles may include thin-walled articles for consumer goods like cellphones, MP3 players, computers, laptops, cameras, video recorders, electronic tablets, hand receivers, kitchen appliances, electrical housings, etc., e.g.
  • a smart meter housing and the like; electrical connectors, and components of lighting fixtures, ornaments, home appliances, roofs, greenhouses, sun rooms, swimming pool enclosures, Light Emitting Diodes (LEDs) and light panels, extruded film and sheet articles; electrical parts, such as relays; and telecommunications parts such as parts for base station terminals.
  • the present disclosure further contemplates additional fabrication operations on said articles, such as, but not limited to, molding, in-mold decoration, baking in a paint oven, lamination, and/or thermoforming.
  • the compositions disclosed are heated to temperatures at which the composition flows, which may be above the glass transition temperatures of the polycarbonates in the composition. Such temperatures may be greater than 155 °C, above 200 °C or greater, 250 °C or greater.
  • Such temperatures may be 400 °C or less or 300 °C or less.
  • the mold may be heated to facilitate processing such as to 50 °C or greater, 80 °C or greater or 100 °C or greater.
  • the articles prepared from the disclosed compositions may include electric vehicle battery enclosures or any other FR demanding application, but particularly in such applications as battery pans, battery lids, battery internal brackets or battery boxes, used in a material conversion process such as compounding, direct fiber compounding and molding, solvent casting, compression molding of molten patty, or combinations of extrusion and compression molding and optional overmolding, or combinations of powder loading and compression molding and optional overmolding with continuous woven and non-woven fibrous systems comprising fiber types such as carbon fiber and glass fiber.
  • the UL-94 vertical test (20 mm vertical burn test) in the UL standards is a measuring method used for an index of flame retardancy in an unexpanded resin. The purpose of the test is to determine the resistance of plastic materials used for parts in devices and appliances to flame and glow propagation.
  • UL 94 is used to measure burning rate and characteristics based on standard samples. Sample size is 12.7mm by 127mm, with the thickness varying. Thickness must be reported when a rating is given. The relevant ratings are: V-2, V-1 and V-0. "V-0" is the most common rating seen in parts where increases in protection from combustion is required. V-0 carries the following requirements:
  • the total flaming combustion time for the ten 10 second flame applications (5 samples, 2 applications each) of more than 50 seconds.
  • None of the five samples may drip flaming particles which ignite dry absorbent cotton located 305 mm below the sample.
  • test specimens having a specific size are perpendicularly attached to a clamp, flame contact is performed for 10 seconds by 20 mm flame. Each of five specimens is clamped 300 mm above a layer of dry cotton. A calibrated flame is applied to the bottom edge of the vertically supported test bar for 10 seconds and any after flame time (t1) is noted. When after flaming ceases the flame is reapplied for an additional 10 seconds and after flame time (t2) and afterglow time (t3) is noted. If one specimen fails, a second set of five can be tested.
  • a composition comprising a polymer having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups, one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom.
  • a composition according to any one of Embodiments 1 to 3 wherein the phenol groups have no substituents on the aromatic rings or substituents on the aromatic rings comprise C M 2 alkyl or a halogen.
  • a composition according to any one of Embodiments 1 to 5 wherein the hydrocarbylene group between the phenol groups of the one or more bisphenols having a hydrocarbylene group comprise C 1.5 alkylene, a C 2-5 alkylidene, a C 5-6 cycloalkylidene, -O-, -SO-, -CO-, -S-, -SO 2 -, or a C 6-12 arylene, on to which other aromatic rings, which optionally contain hetero atoms, can be condensed.
  • a composition according to any one of Embodiments 1 to 5 wherein the hydrocarbylene group between the phenol groups of the one or more bisphenols having a hydrocarbylene group comprise a C i_ 5 alkylene.
  • a composition according to any one of Embodiments 1 to 7 wherein the hydrocarbylene group containing a triple bond of the one or more bisphenols having a hydro-carbylene group containing a triple bond disposed between the phenol groups comprises a C 2 to 2o alkylene group containing a triple bond, or a C 2 toio alkylene group containing a triple bond.
  • a composition according to any one of Embodiments 1 to 7 wherein the hydrocarbylene group containing a triple bond of the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups comprises a C 2 alkylene group containing a triple bond.
  • A is separately in each occurrence C 1.5 alkylene, C 2-5 alkylidene, C 5-6 cycloalkylidene, -O-, -SO-, -CO-, -S-, -SO 2 -, or C 6 -I 2 arylene, on to which other aromatic rings, which optionally contain hetero atoms, can be condensed:
  • B is separately in each occurrence a C M 2 alkyl or a halogen
  • D is separately in each occurrence a C 2 10 2 o alkynylene group containing a triple bond in the backbone or a C 2 to 2 o alkylene group, C 6 -is arylene group or C 7-2 4 alkarylene group, wherein the triple bond pendant from such groups;
  • G is a direct bond or a linking group capable of bonding to the diphenolic ring and the triple bond; and x in each case is mutually independently 0, 1 , or 2.
  • A is separately in each occurrence C 1-5 alkylene
  • B is separately in each occurrence a methyl or chlorine and/or bromine
  • D is separately in each occurrence a C 2 alkylene group containing a triple bond.
  • B is separately in each occurrence a C 1-12 alkyl or a halogen
  • D is separately in each occurrence a C 2 to 20 alkynylene group containing a triple bond in the backbone or a C 2 to 20 alkylene group, C 6-18 arylene group or C 7-24 alkarylene group, wherein the triple bond pendant from such groups;
  • G is a direct bond or a linking group capable of bonding to the diphenolic ring and the triple bond;and x in each case is mutually independently 0, 1 , or 2.
  • A is separately in each occurrence C 1-5 alkylene
  • B is separately in each occurrence a methyl or chlorine and/or bromine
  • D is separately in each occurrence a C 2 alkylene group containing a triple bond
  • a composition according to Embodiment 19 or 20 wherein the one or more non-halogen containing flame retardants comprise a phosphorous containing flame retardant, preferably one or more of phosphate esters or phosphazenes.
  • a composition according to Embodiment 19 or 20 wherein the one or more non-halogen containing flame retardants comprise one or more phosphate esters.
  • a composition according to any one of the preceding Embodiments the polycarbonate formed has a terminal encapping agent with a triple bond such group may correspond to the formula wherein G is as defined hereinbefore or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom wherein.
  • G is as defined hereinbefore or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom wherein.
  • a composition comprising a blend of polymers wherein the first polymer is a polycarbonate polymer having monomer units derived from one or more biphenols having a direct bond between the phenol groups and the second is a polycarbonate polymer having monomer units derived from one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom
  • a composition according to Embodiment 25 comprising a blend of polymers wherein the first polymer is a polycarbonate homopolymer having monomer units derived from one or more biphenols having a direct bond between the phenol groups and the second is a polycarbonate homopolymer having monomer units derived from one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom and the third polymer which is a polycarbonate homopolymer derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups.
  • a composition according to Embodiment 24 comprising the blend of two polymers wherein the first polymer is a polycarbonate polymer having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups and biphenol having a direct bond between the phenol groups and the second is polymer having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups, and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom.
  • the first polymer is a polycarbonate polymer having monomer units derived from one or more bisphenols having a hydrocarby
  • a composition according to Embodiment 24 comprising a third polymer comprising a polymer having monomer units derived from one or more bisphenols having a hydrocarbylene group, -O-, -SO-, -CO-, -S-, or a -SO 2 - between the phenol groups.
  • a composition according to Embodiment 24 to 29 wherein the phenol groups have no substituents on the aromatic rings or substituents on the aromatic rings comprise C 1.12 alkyl or a halogen.
  • a composition according to any one of Embodiments 24 to 32 wherein the hydrocarbylene group between the phenol groups of the one or more bisphenols having a hydrocarbylene group comprise C 1.5 alkylene, a C 2-5 alkylidene, a C 5-6 cycloalkylidene, -O-, -SO- , -CO-, -S-, -SO2-, or a C 6-12 arylene, on to which other aromatic rings, which optionally contain hetero atoms, can be condensed.
  • a composition according to any one of Embodiments 24 to 33 wherein the hydrocarbylene group between the phenol groups of the one or more bisphenols having a hydrocarbylene group comprise a C 1.5 alkylene.
  • a composition according to any one of Embodiments 24 to 34 wherein the hydrocarbylene group containing a triple bond of the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups comprises a C 2 to 20 alkylene group containing a triple bond, or a C 2 toio alkylene group containing a triple bond.
  • a composition according to any one of Embodiments 24 to 34 wherein the hydrocarbylene group containing a triple bond of the one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups comprises a C 2 alkylene group containing a triple bond.
  • A is separately in each occurrence C 1-5 alkylene, C 2-5 alkylidene, C 5-6 cycloalkylidene, -O-, -SO-, -CO-, -S-, -SO2-, or C 6-12 arylene, on to which other aromatic rings, which optionally contain hetero atoms, can be condensed:
  • B is separately in each occurrence a C 1-12 alkyl or a halogen
  • D is separately in each occurrence a C 2 to 20 alkynylene group containing a triple bond in the backbone or a C 2 to 2o alkylene group, C 6 -is arylene group or C 7-24 alkarylene group, wherein the triple bond pendant from such groups;
  • G is a direct bond or a linking group capable of bonding to the diphenolic ring and the triple bond; and x in each case is mutually independently 0, 1 , or 2.
  • A is separately in each occurrence C 1-5 alkylene
  • B is separately in each occurrence a methyl or chlorine and/or bromine
  • D is separately in each occurrence a C 2 alkylene group containing a triple bond.
  • one or more biphenols having a direct bond between the phenol groups corresponding to the formula and/ or one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups or pendant from a group between the phenol groups or derived from one or more diphenols having a triple bond pendant therefrom corresponding to one of the formulas;
  • A is separately in each occurrence C 1-5 alkylene, C 2-5 alkylidene, C 5-6 cycloalkylidene, -O-, -SO-, -CO-, -S-, -SO2-, or C 6-12 arylene, on to which other aromatic rings, which optionally contain hetero atoms, can be condensed:
  • B is separately in each occurrence a C 1-12 alkyl or a halogen
  • D is separately in each occurrence a C 2 to 20 alkynylene group containing a triple bond in the backbone or a C 2 to 2o alkylene group, C 6 -is arylene group or C 7-24 alkarylene group, wherein the triple bond pendant from such groups;
  • G is a direct bond or a linking group capable of bonding to the diphenolic ring and the triple bond;and x in each case is mutually independently 0, 1 , or 2.
  • A is separately in each occurrence C 1-5 alkylene
  • B is separately in each occurrence a methyl or chlorine and/or bromine
  • D is separately in each occurrence a C 2 alkylene group containing a triple bond
  • [0105] 45 A composition according to any one of Embodiments 24 to 44 wherein the polymer blend exhibits a percent char of greater than 20 percent when measured using thermogravimetric analysis at 800 °C in nitrogen wherein there is no additional flame retardant or antidrip agent present.
  • a composition according to Embodiment 46 or 47 wherein the one or more non-halogen containing flame retardants comprise a phosphorous containing flame retardant, preferably one or more of phosphate esters or phosphazenes.
  • a composition according to Embodiment 46 or 47 wherein the one or more non-halogen containing flame retardants comprise one or more phosphate esters.
  • a composition comprising a copolymer comprising having monomer units derived from one or more biphenols having a direct bond between the phenol groups and one or more bisphenols having a hydrocarbylene group containing a triple bond disposed between the phenol groups.
  • Polycarbonate made with 60 mole percent bisphenol A, 20 mole percent bisphenol acetylene and 20 percent 4,4’-biphenol is synthesized by phosgene interfacial polycondensation to give a material with Tg of 180°C and a Mw of 25000 with polydispersity of 2.9. Without any PFAS containing additive the material yields a V0 performance at 1.0 mm thickness.
  • Polycarbonate copolymers and terpolymers are synthesized according to a typical melt polymerization process.
  • a mixture of the comonomers (1 eq) and diphenyl carbonate (1.05 eq) is first prepared according to the ratios in Table 1 in a round bottom flask, and afterwards a catalytic amount of KOH is added ( ⁇ 0.2 mol%).
  • the flask is equipped with a magnetic stirring bar and condenser with vacuum port, before the flask is lowered into a sand bath at 160 - 180 °C to melt the monomers. Once the monomers are molten, the mixture is stirred for 10 minutes. Next, the temperature is raised slowly to 220 °C, and the pressure is reduced to 600 mbar.
  • “Char” is determined by thermo gravimetric analysis (TGA) under nitrogen atmosphere and reported in percent based on the initial sample weight. The weight retention at 550 °C and 800 °C is considered to be a proper measurement of char content that is formed from a sample.
  • “Mn”, “Mw”, and B are number average molecular weight, weight average molecular weight, and dispersity respectively. These values were determined by size exclusion chromatography (SEC) using polystyrene standards.
  • SEC size exclusion chromatography

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Abstract

L'invention concerne des terpolymères de polycarbonate et des mélanges de polymères contenant des unités monomères dérivées de biphénols et de bisphénols à pont acétylène, des bisphénols ayant des groupes acétylène se ramifiant à partir du groupe de pontage et/ou des groupes acétylène sur des groupes terminaux et des procédés de préparation de tels terpolymères et mélanges de polymères. Les terpolymères et les mélanges de polymères comprennent en outre des motifs monomères dérivés d'un ou de plusieurs bisphénols ayant un groupe hydrocarbylène, - O-, -SO-, -CO-, -S-, ou -SO2- entre les groupes phénol. L'invention concerne des systèmes polymères ignifuges contenant de telles unités monomères.
PCT/EP2025/056454 2024-03-12 2025-03-10 Compositions de polycarbonate contenant des unités monomères de biphénols et de bisphénols à pont acétylène Pending WO2025190859A1 (fr)

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028365A (en) 1953-10-16 1962-04-03 Bayer Ag Thermoplastic aromatic polycarbonates and their manufacture
US3419634A (en) 1966-01-03 1968-12-31 Gen Electric Organopolysiloxane polycarbonate block copolymers
US4529791A (en) 1981-01-28 1985-07-16 The Dow Chemical Company Interfacial polycarbonate preparation by adding additional solvent
US4677162A (en) 1983-04-15 1987-06-30 Mobay Corporation Polycarbonate blends having low gloss
US5212209A (en) 1991-11-18 1993-05-18 The Dow Chemical Company Compatibilized internal mold release composition for preparations of foamed and fiber-reinforced polymeric articles
US7645850B2 (en) 2005-08-11 2010-01-12 Frx Polymers, Inc. Poly(block-phosphonato-ester) and poly(block-phosphonato-carbonate) and methods of making same
WO2010086385A1 (fr) 2009-01-28 2010-08-05 Nexam Chemicals Ab Polycarbonate aromatique réticulable
EP2561004B1 (fr) * 2010-04-22 2014-04-02 Styron Europe GmbH Copolymère de polycarbonate
US10100192B2 (en) 2013-06-13 2018-10-16 Polyone Corporation Completely non-halogenated flame retardant polycarbonate compounds
WO2019115506A1 (fr) 2017-12-14 2019-06-20 Trinseo Europe Gmbh Stratifié contenant des couches de composition de polycarbonate et des couches de structure fibreuse ayant des propriétés de résistance au feu améliorées
US20230167296A1 (en) 2020-05-22 2023-06-01 Covestro Deutschland Ag Flame-retardant polycarbonate composition

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028365A (en) 1953-10-16 1962-04-03 Bayer Ag Thermoplastic aromatic polycarbonates and their manufacture
US3419634A (en) 1966-01-03 1968-12-31 Gen Electric Organopolysiloxane polycarbonate block copolymers
US4529791A (en) 1981-01-28 1985-07-16 The Dow Chemical Company Interfacial polycarbonate preparation by adding additional solvent
US4677162A (en) 1983-04-15 1987-06-30 Mobay Corporation Polycarbonate blends having low gloss
US5212209A (en) 1991-11-18 1993-05-18 The Dow Chemical Company Compatibilized internal mold release composition for preparations of foamed and fiber-reinforced polymeric articles
US7645850B2 (en) 2005-08-11 2010-01-12 Frx Polymers, Inc. Poly(block-phosphonato-ester) and poly(block-phosphonato-carbonate) and methods of making same
WO2010086385A1 (fr) 2009-01-28 2010-08-05 Nexam Chemicals Ab Polycarbonate aromatique réticulable
EP2561004B1 (fr) * 2010-04-22 2014-04-02 Styron Europe GmbH Copolymère de polycarbonate
US10100192B2 (en) 2013-06-13 2018-10-16 Polyone Corporation Completely non-halogenated flame retardant polycarbonate compounds
WO2019115506A1 (fr) 2017-12-14 2019-06-20 Trinseo Europe Gmbh Stratifié contenant des couches de composition de polycarbonate et des couches de structure fibreuse ayant des propriétés de résistance au feu améliorées
US20230167296A1 (en) 2020-05-22 2023-06-01 Covestro Deutschland Ag Flame-retardant polycarbonate composition

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