Stabilizing polycarbonates
AssigneeCiba Specialty Chemicals Corporation
InventorsAndré Schmitter, Alfred Georges Oertli
Life of this patent
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Abstract
This invention relates to compositions comprising a polycarbonate, polyester or polyketone which is subject to oxidative, thermal and/or light-induced degradation, or their mixtures and blends, and at least one benzofuran-2-one type compound, to the use thereof for stabilising polycarbonate, polyester or polyketone or their mixtures or blends against oxidative, thermal and/or light-induced degradation, as well as to a process for stabilising these plastic materials.
Claims11
A composition, which comprises
- a) a transparent, solid and vitreous moulded article which is transparent at a wavelength of 350 to 700 nm and composed of a polycarbonate, polyester or polyketone or a mixture thereof which is subject to oxidative, thermal and/or light-induced degradation, and
- b) at least one benzofuran-2-one compound of formula I
- wherein,
- if n=1,
- R1 is naphthyl, phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo[b]thienyl, naphtho[2,3-b]thienyl, thianthrenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxathiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, β-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, biphenyl, terphenyl, fluorenyl or phenoxazinyl, each of which is unsubstituted or substituted by C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, hydroxy, halogen, amino, C1-C4alkylamino, phenylamino or di(C1-C4-alkyl)amino, or R1 is a radical of formula II
- and,
- if n=2,
- R1 is unsubstituted or C1-C4alkyl- or hydroxy-substituted phenylene or naphthylene;
- or —R12—X—R13—, R2R3, R4 and R5 are each independently of one another hydrogen, chloro, hydroxy, C1-C25-alkyl, C7-C9phenylalkyl, unsubstituted or C1-C4alkyl-substituted phenyl;
- unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkyl;
- C1-C18alkoxy, C1-C18alkylthio, C1-C4alkylamino, di(C1-C4-alkyl)amino, C1-C25alkanoyloxy, C1-C25alkanoylamino, C3-C25alkenoyloxy;
- C3-C25alkanoyloxy which is interrupted by oxygen, sulfur or
- C6-C9cycloalkylcarbonyloxy, benzoyloxy or C1-C12alkyl-subsbtuted benzoyloxy;
- or R2 and R3, or R3 and R4, or R4 and R5, together with the linking carbon atoms, form a benzene ring, R4 is additional —(CH2)p—COR15 or —(CH2)qOH or, if R3, R5 and R6 are hydrogen, R4 is additionally a radical of formula III
- wherein
- R1 is as defined above for n=1,
- R6 is hydrogen or a radical of formula IV
- wherein
- R4 is not a radical of formula III, and R1 is as defined above for n=1,
- R7, R8, R9, R10 and R11 are each independently of one another hydrogen, halogen, hydroxy, C1-C25alkyl;
- C2-C25alkyl which is interrupted by oxygen, sulfur or
- C1-C25alkoxy;
- C2-C25alkoxy which is interrupted by oxygen, sulfur or
- C1-C25alkylthio, C3-C25-alkenyl, C3-C25alkenyloxy, C3-C25alkynyl, C3-C25alkynyloxy, C7-C9phenylalkyl, C7-C9phenylalkoxy, unsubstituted or C1-C4alkyl-substituted phenyl;
- unsubstituted or C1-C4alkyl-substituted phenoxy;
- unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkyl;
- unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkoxy;
- C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C25alkanoyl;
- C3-C25alkanoyl which is interrupted by oxygen, sulfur or
- C1-C25alkanoyloxy;
- C3-C25alkanoyloxy which is interrupted by oxygen, sulfur or
- C1-C25alkanoylamino, C3-C25alkenoyl;
- C3-C25alkenoyl which is interrupted by oxygen, sulfur or
- C3-C25alkenoyloxy;
- C3-C25alkenoyloxy which is interrupted by oxygen, sulfur or
- C6-C9cycloalkylcarbonyl, C6-C9cycloalkylcarbonyloxy, benzoyl or C1-C12alkyl-substituted benzoyl;
- benzoyloxy or C1-C12alkyl-substituted benzoyloxy;
- or in formula II,
- R7, and R8, or R8 and R11, together with the linking carbon atoms, form a benzene ring,
- R12 and R13 are each independently of the other unsubstituted or C1-C4alkyl-substituted phenylene or naphthylene,
- R14 is hydrogen or C1-C8alkyl,
- R15 is hydroxy,
- C1-C18alkoxy or
- R16 and R17 are each independently of the other hydrogen, CF3, C1-C12alkyl or phenyl, or R16 and R17, together with the linking carbon atom, are a C5-C8cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C1-C4alkyl;
- R18 and R19 are each independently of the other hydrogen, C1-C4alkyl or phenyl,
- R20 is hydrogen or C1-C4alkyl,
- R21 is hydrogen, unsubstituted or C1-C4alkyl-substituted phenyl;
- C1-C25alkyl;
- C2-C25alkyl which is interrupted by oxygen, sulfur or
- C7-C9phenylalkyl which is unsubstituted or substituted at the phenyl moiety by 1 to 3 C1-C4alkyl;
- C7-C25phenylalkyl which is interrupted by oxygen, sulfur or
- and which is unsubstituted or substituted at the phenyl moiety by 1 to 3 C1-C4alkyl or, R20 and R21, together with the linking carbon atoms, form a C5-C12cycloalkylene ring which is unsubstituted or substituted by 1 to 3 C1-C4alkyl;
- R22 is hydrogen or C1-C4alkyl,
- R23 is hydrogen, C1-C25alkanoyl, C3-C25alkenoyl;
- C3-C25alkanoyl which is interrupted by oxygen, sulfur or
- C2-C25alkanoyl which is substituted by a di(C1-C6alkyl)phosphonate group;
- C6-C9cycloalkylcarbonyl, thienoyl, furoyl, benzoyl or C1-C12alkyl-substituted benzoyl;
- R24 and R25 are each independently of the other hydrogen or C1-C18alkyl,
- R26 is hydrogen or C1-C8alkyl,
- R27 is a direct bond, C1-C18alkylene;
- C2-C18alkylene which is interrupted by oxygen, sulfur or
- C2-C18alkenylene, C2-C20alkylidene, C7-C20phenylalkylidene, C5-C8cyclo alkylene, C7-C8bicycloalkylene, unsubstituted or C1-C4alkyl-substituted phenylene,
- or
- R28 is hydroxy
- C1-C18alkyloxy or
- R29 is oxygen, —NH— or
- R30 is C1-C18alkyl or phenyl,
- R31 is hydrogen or C1-C18alkyl,
- M is an r-valent metal cation,
- X is a direct bond, oxygen, sulfur or —NR31—,
- n is 1 or 2,
- p is 0, 1 or 2,
- q is 1, 2, 3, 4, 5 or 6,
- r is 1, 2 or 3, and
- s is 0, 1 or 2.
A method of stabilising a transparent, solid and vitreous moulded article which is transparent at a wavelength of 350 to 700 nm and composed of a polycarbonate, polyester or polyketone or their mixtures against oxidative, thermal and/or light-induced degradation, which comprises incorporating therein, or applying thereto, at least one benzofuran-2-one compound of formula I
- wherein,
- if n=1,
- R1 is naphthyl, phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo[b]thienyl, naphtho[2,3-b]thienyl, thianthrenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxathiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, β-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, biphenyl, terphenyl, fluorenyl or phenoxazinyl, each of which is unsubstituted or substituted by C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, hydroxy, halogen, amino, C1-C4alkylamino, phenylamino or di(C1-C4-alkyl)amino, or R1 is a radical of formula II
- and,
- if n=2,
- R1 is unsubstituted or C1-C4alkyl- or hydroxy-substituted phenylene or naphthylene;
- or —R12—X—R13—, R2, R3, R4 and R5 are each independently of one another hydrogen, chloro, hydroxy, C1-C25-alkyl, C7-C9phenylalkyl, unsubstituted or C1-C4alkyl-substituted phenyl;
- unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkyl;
- C1-C18alkoxy, C1-C18alkylthio, C1-C4alkylamino, di(C1-C4-alkyl)amino, C1-C25alkanoyloxy, C1-C25alkanoylamino, C3-C25alkenoyloxy;
- C3-C25alkanoyloxy which is interrupted by oxygen, sulfur or
- C6-C9cycloalkylcarbonyloxy, benzoyloxy or C1-C12alkyl-substituted benzoyloxy;
- or R2 and R3, or R3 and R4, or R4 and R5, together with the linking carbon atoms, form a benzene ring, R4 is additionally —(CH2)p—COR15 or —(CH2)qOH or, if R3, R5 and R6 are hydrogen, R4 is additionally a radical of formula III
- wherein
- R1 is as defined above for n=1,
- R6 is hydrogen or a radical of formula IV
- wherein
- R4 is not a radical of formula III, and R1 is as defined above for n=1
- R7, R8, R9, R10 and R11 are each independently of one another hydrogen, halogen, hydroxy, C1-C25alkyl which is interrupted by oxygen, sulfur or
- C1-C25alkoxy;
- C2-C25alkoxy which is interrupted by oxygen, sulfur or
- C1-C25alkylthio, C3-C25-alkenyl, C3-C25alkenyloxy, C3-C25alkynyl, C3-C25alkynyloxy, C7-C9phenylalkyl, C7-C9phenylalkoxy, unsubstituted or C1-C4alkyl-substituted phenyl;
- unsubstituted or C1-C4alkyl-substituted phenoxy;
- unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkyl;
- unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkoxy;
- C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C25alkanoyl;
- C3-C25alkanoyl which is interrupted by oxygen, sulfur or
- C1-C25alkanoyloxy;
- C3-C25alkanoyloxy which is interrupted by oxygen, sulfur or
- C1-C25alkanoylamino, C3-C25alkenoyl;
- C3-C25alkenoyl which is interrupted by oxygen, sulfur or
- C3-C25alkonoyloxy, C3-C25alkenoyloxy which is interrupted by oxygen, sulfur or
- C6-C9cycloalkylcarbonyl C8-C9cycloalkylcarbonyloxy, benzoyl or C1-C12alkyl-substituted benzoyl;
- benzoyloxy or C1-C12alkyl-substituted benzoyloxy;
- or in formula II,
- R7 and R8, or R8and R11, together with the linking carbon atoms, form a benzene ring,
- R12 and R13 are each independently of the other unsubstituted or C1-C4alkyl-substituted phenylene;
- or naphthylene,
- R14 is hydrogen or C1-C8alkyl,
- R15 is hydroxy,
- C1-C18alkoxy or
- R16 and R17 are each independently of the other hydrogen, CF3, C1-C12alkyl or phenyl, or R16 and R17, together with the linking carbon atom, are a C5-C8cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C1-C4alkyl;
- R18 and R19 are each independently of the other hydrogen, C1-C4alkyl or phenyl,
- R20 is hydrogen or C1-C4alkyl, R21 is hydrogen, unsubstituted or C1-C4alkyl-substituted phenyl;
- C1-C25alkyl;
- C2-C25alkyl which is interrupted by oxygen, sulfur or
- C7-C9phenylalkyl which is unsubstituted or substituted at the phenyl moiety by 1 to 3 C1-C4alkyl;
- C7-C25phenylalkyl which is interrupted by oxygen, sulfur or
- and which is unsubstituted or substituted at the phenyl moiety by 1 to 3 C1-C4alkyl, or R20 and R21, together with the linking carbon atoms, form a C5-C12cycloalkylene ring which is unsubstituted or substituted by 1 to 3 C1-C4alkyl;
- R22 is hydrogen or C1-C4alkyl,
- R23 is hydrogen, C1-C25alkanoyl, C3-C25alkenoyl;
- C3-C25alkanoyl which is interrupted by oxygen, sulfur or
- C2-C25 alkanoyl which is substituted by a di(C1-C6alkyl)phosphonate group;
- C6-C9cycloalkylcarbonyl, thienoyl, furoyl, benzoyl or C1-C12alkyl-substituted benzoyl;
- R24 and R25are each independently of the other hydrogen or C1-C18alkyl,
- R26 is hydrogen or C1-C8alkyl,
- R27 is a direct bond, C1-C18alkylene;
- C2-C18alkylene which is interrupted by oxygen, sulfur or
- C2-C18alkenylene, C2-C20alkylidene, C7-C20phenylalkylidene, C5-C8cyclo alkylene, C7-C8bicycloalkylene, unsubstituted or C1-C4alkyl-substituted phenylene,
- or
- R28 is hydroxy,
- C1-C18alkoxy or
- R29 is oxygen, —NH— or
- R30 is C1-C18alkyl or phenyl,
- R31 is hydrogen or C1-C18alkyl,
- M is an r-valent metal cation,
- X is a direct bond, oxygen, sulfur or —NR31 —,
- n is 1 or 2,
- p is 0, 1 or 2,
- q is 1, 2, 3, 4, 5 or 6,
- r is 1, 2 or 3, and
- s is 0, 1 or 2.
Dependencies are inferred from the claim text.