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    • 专利摘要:
    The present invention provides a composition comprising a polycarbonate, polyester or polyketone, or mixtures and combinations thereof, and compounds of one or more benzofuran-2-one types that are susceptible to degradation by oxidation, heat and / or photoinduction. And stabilizing polycarbonates, polyesters or polyketones or mixtures or combinations thereof from decomposition by oxidation, heat and / or photoinduction, as well as methods of stabilizing these plastic materials.
    公开号:KR19980079962A
    申请号:KR1019980007415
    申请日:1998-03-06
    公开日:1998-11-25
    发明作者:앙드레 슈미터；알프레트 게오르게스 오에르트리
    申请人:피로스카 랍 보프；시바 스페셜티 케미칼스 홀딩 인코포레이티드；
    IPC主号:
    专利说明:

    A composition comprising a polycarbonate, polyester or polyketone and a compound of at least one benzofuran-2-one type
    The present invention provides a composition comprising a polycarbonate, polyester or polyketone, or mixtures and combinations thereof, and compounds of one or more benzofuran-2-one types that are susceptible to degradation by oxidation, heat and / or photoinduction. And stabilizing polycarbonates, polyesters or polyketones or mixtures or combinations thereof from decomposition by oxidation, heat and / or photoinduction, as well as methods of stabilizing these plastic materials.
    In particular, R. Gachter and H. Muller, published in Plastic Additives Handbook, 3rd Edition, page 88/89 (1990), show that triarylphosphites or phosphonites and any phenolic compounds during the manufacture, processing and use of polycarbonates. It is known that it can be protected from oxidation by a suitable stabilizer mixture comprising antioxidants.
    These known stabilizer mixtures have high demands on stabilizer mixtures in all respects, especially in reinforcement of storage stability, water absorption, hydrolysis sensitivity, process stabilization, color change, light transmittance, volatility, mobility, compatibility and light stabilization. We do not meet. In the case of amorphous plastics used for example as glass substitutes, discoloration and reduced transparency during the processing or use of the plastics are undesirable. In the case of polyesters in contact with beverages, especially PET, the degradation products of polyesters such as formaldehyde or acetaldehyde are very undesirable because they can affect the taste of the beverage even at low temperatures. Thus, polycarbonates, polyesters or polyketones or these, which significantly prevent sulfidation of plastics and release decomposition products of plastics without exposure to light or substantially reducing the transparency of the plastics to the oxidation state or thermal stress There has been a need for effective stabilizers for mixtures or blends of.
    The use of compounds of the benzofuran-2-one type as stabilizers for organic polymers, in particular polyolefins, is for example described in U.S. 4,325,863; U.S. 4,388,244; U.S. 5,175,312; U.S. 5,252,643; U.S. 5,216,052; U.S. 5,369,159; U.S. 5,488,117; U.S. 5,356,966; U.S. 5,367,008; U.S. 5,428,162; U.S. 5,428,177 or U.S. Known from US Pat. No. 5,516,920.
    It has been found that compounds of the benzofuran-2-one type are particularly suitable as stabilizers for polycarbonates, polyesters or polyketones or mixtures or combinations thereof.
    It is a problem of the present invention to stabilize a compound from degradation by oxidation, heat and / or photoinduction.
    The present invention
    a) polycarbonates, polyesters or polyketones, or mixtures or combinations thereof, susceptible to degradation by oxidation, heat and / or light induction, and
    b) a composition comprising at least one compound of the benzofuran-2-one type.
    An important composition is that component (b) is a compound of formula (1):
    Where
    If n is 1,
    R 1 is unsubstituted or C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 -alkylthio, hydroxy, halogen, amino, C 1 -C 4 alkylamino, phenylamino or di ( Naphthyl, phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1 substituted by C 1 -C 4 -alkyl) amino Naphthyl, thienyl, benzo [b] thienyl, naphtho [2,3-b] thienyl, thianthrenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxatiinyl, pyrrolyl, imi Dazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolinyl, isoindolyl, indolyl, indazolyl, furinyl, quinolinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyl Lidinyl, quinoxalinyl, quinazolinyl, cynolinyl, putridinyl, carbazolyl, β-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothia Zolyl, phenothiazinyl, isoxazolyl, furazanyl, biphenyl, Terphenyl, fluorenyl or phenoxazinyl, or R 1 is a radical of the formula (2):
    if n is 2,
    R 1 is unsubstituted or C 1 -C 4 alkyl- or hydroxy-substituted phenylene or naphthylene; Or -R 12 -XR 13- ,
    R 2 , R 3 , R 4 and R 5 independently of one another are hydrogen, chloro, hydroxy, C 1 -C 25 -alkyl, C 7 -C 9 phenylalkyl, unsubstituted or C 1 -C 4 alkyl-substituted Phenyl; Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkyl; C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl) amino, C 1 -C 25 alkanoyloxy, C 1 -C 25 alkanoyl Amino, C 3 -C 25 alkenoyloxy; Oxygen, sulfur or in the middle of the chain C 3 -C 25 -alkanoyloxy comprising; C 6 -C 9 cycloalkylcarbonyloxy, benzoyloxy or C 1 -C 12 alkyl-substituted benzoyloxy; Or R 2 and R 3 , or R 3 and R 4 , or R 4 and R 5 , combine with the linking carbon atom to form a benzene ring or R 4 is additionally-(CH 2 ) p -COR 15 or-(CH 2 ) q OH, or if R 3 , R 5 and R 6 are hydrogen, R 4 is additionally a radical of the formula (3):
    In this case, R 1 is as described above for n = 1,
    R 6 is hydrogen or a radical of formula (4):
    Where
    R 4 is not a radical of formula (3) and R 1 is as described above for n = 1,
    R 7 , R 8 , R 9 , R 10 and R 11 independently of one another are hydrogen, halogen, hydroxy, C 1 -C 25 alkyl; Oxygen, sulfur or in the middle of the chain C 2 -C 25 alkyl comprising; C 1 -C 25 alkoxy; Oxygen, sulfur or in the middle of the chain C 2 -C 25 -alkoxy including; C 1 -C 25 alkylthio, C 3 -C 25 alkenyl, C 3 -C 25 -alkenyloxy, C 3 -C 25 alkynyl, C 3 -C 25 alkynyloxy, C 7 -C 9 phenylalkyl , C 7 -C 9 phenylalkoxy, unsubstituted or C 1 -C 4 alkyl-substituted phenyl; Unsubstituted or C 1 -C 4 alkyl-substituted phenoxy; Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkyl; Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkoxy; C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl) amino, C 1 -C 25 alkanoyl; Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkanoyl comprising; C 1 -C 25 alkanoyloxy; Oxygen, sulfur or in the middle of the chain C 3 -C 25 -alkanoyloxy comprising; C 1 -C 25 alkanoylamino, C 3 -C 25 alkenoyl; Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkenoyl comprising; C 3 -C 25 alkenoyloxy; Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkenoyloxy comprising; C 6 -C 9 cycloalkylcarbonyl, C 6 -C 9 cycloalkylcarbonyloxy, benzoyl or C 1 -C 12 alkyl-substituted benzoyl; Benzoyloxy or C 1 -C 12 -alkyl-substituted benzoyloxy; or Or in formula (2) R 7 and R 8 , or R 8 and R 11 , combine with the linking carbon atom to form a benzene ring,
    R 12 and R 13 are independently of each other unsubstituted or C 1 -C 4 alkyl-substituted phenylene or naphthylene,
    R 14 is hydrogen or C 1 -C 8 alkyl,
    R 15 is hydroxy, , C 1 -C 18 alkoxy or ,
    R 16 and R 17 are independently of each other hydrogen, CF 3 , C 1 -C 12 alkyl or phenyl, or R 16 and R 17 are unsubstituted in combination with a linking carbon atom or 1 to 3 C 1 -C 4 alkyl A C 5 -C 8 cycloalkylidene ring substituted by;
    R 18 and R 19 are independently of each other hydrogen, C 1 -C 4 alkyl or phenyl,
    R 20 is hydrogen or C 1 -C 4 alkyl,
    R 21 is hydrogen, unsubstituted or C 1 -C 4 alkyl-substituted phenyl; C 1 -C 25 alkyl; Oxygen, sulfur or in the middle of the chain C 2 -C 25 alkyl comprising; C 7 -C 9 phenylalkyl unsubstituted on phenyl or substituted by 1 to 3 C 1 -C 4 alkyl; Oxygen, sulfur or in the middle of the chain Or C 7 -C 25 phenylalkyl which is unsubstituted on phenyl or substituted by 1 to 3 C 1 -C 4 alkyl, or R 20 and R 21 are unsubstituted in combination with a linking carbon atom or 1 To form a C 5 -C 12 cycloalkylene ring substituted by 3 to 3 C 1 -C 4 alkyl;
    R 22 is hydrogen or C 1 -C 4 alkyl,
    R 23 is hydrogen, C 1 -C 25 alkanoyl, C 3 -C 25 alkenoyl; Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkanoyl comprising; C 2 -C 25 alkanoyl substituted by di (C 1 -C 6 alkyl) phosphonate groups; C 6 -C 9 cycloalkylcarbonyl, tenoyl, furoyl, benzoyl or C 1 -C 12 alkyl-substituted benzoyl;
    or ,
    R 24 and R 25 are independently of each other hydrogen or C 1 -C 18 alkyl,
    R 26 is hydrogen or C 1 -C 8 alkyl,
    R 27 is a direct bond, C 1 -C 18 alkylene; Oxygen, sulfur or in the middle of the chain C 2 -C 18 alkylene comprising; C 2 -C 18 alkenylene, C 2 -C 20 alkylidene, C 7 -C 20 phenylalkylidene, C 5 -C 8 cycloalkylene, C 7 -C 8 bicycloalkylene, unsubstituted or C 1 -C 4 alkyl-substituted phenylene, or ego,
    R 28 is hydroxy, , C 1 -C 18 alkoxy or ,
    R 29 is oxygen, -NH- or ego,
    R 30 is C 1 -C 18 alkyl or phenyl,
    R 31 is hydrogen or C 1 -C 18 alkyl,
    M is a r-valent metal cation,
    X is a direct bond, oxygen, sulfur or -NR 31- ,
    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.
    Unsubstituted or C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, hydroxy, halogen, amino, C 1 -C 4 alkylamino, phenylamino or di (C 1 -C 4 Alkyl) amino substituted 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, cromenyl, xanthenyl, phenoxatiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyra Geniyl, pyrimidinyl, pyridazinyl, idolzinyl, isoindoleyl, indolyl, indazolyl, furinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, Quinazolinyl, Cinolinyl, Pterridinyl, Carbazolyl, β-Carbolinyl, Phenantridinyl, Acridinyl, Perimidinyl, Phenanthrolinyl, Phenazinyl, Isothiazolyl, Phenothiazinyl, Isox Sazolyl, furazanyl, biphenyl, terphenyl, fluorine Neyl or phenoxazinyl is, for example, 1-naphthyl, 2-naphthyl, 1-phenylamino-4-naphthyl, 1-methylnaphthyl, 2-methylnaphthyl, 1-methoxy-2-naphthyl, 2 -Methoxy-1-naphthyl, 1-dimethylamino-2-naphthyl, 1,2-dimethyl-4-naphthyl, 1,2-dimethyl-6-naphthyl, 1,2-dimethyl-7-naph Teal, 1,3-dimethyl-6-naphthyl, 1,4-dimethyl-6-naphthyl, 1,5-dimethyl-2-naphthyl, 1,6-dimethyl-2-naphthyl, 1-hydroxy -2-naphthyl, 2-hydroxy-1-naphthyl, 1,4-dihydroxy-2-naphthyl, 7-phenanthryl, 1-anthryl, 2-anthryl, 9-anthryl, 3 -Benzo [b] thienyl, 5-benzo [b] thienyl, 2-benzo [b] thienyl, 4-dibenzofuryl, 4,7-dibenzofuryl, 4-methyl-7-dibenzofuryl, 2-xanthenyl, 8-methyl-2-xanthenyl, 3-xanthenyl, 2-phenoxatiinyl, 2,7-phenoxathinyl, 2-pyrrolyl, 3-pyrrolyl, 5- Methyl-3-pyrrolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-methyl-4-imidazolyl, 2-ethyl-4-imidazolyl, 2-ethyl-5 Imidazolyl, 3-pyrazolyl, 1-meth Tyl-3-pyrazolyl, 1-propyl-4-pyrazolyl, 2-pyrazinyl, 5,6-dimethyl-2-pyrazinyl, 2-indolizinyl, 2-methyl-3-isoindolyl, 2- Methyl-1-isoindolyl, 1-methyl-2-indolyl, 1-methyl-3-indolyl, 1,5-dimethyl-2-indolyl, 1-methyl-3-indazolyl, 2,7- Dimethyl-8-furinyl, 2-methoxy-7-methyl-8-furinyl, 2-quinolinyl, 3-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, isoquinolyl, 3 -Methoxy-6-isoquinolyl, 2-quinolyl, 6-quinolyl, 7-quinolyl, 2-methoxy-3-quinolyl, 2-methoxy-6-quinolyl, 6-phthalazinyl , 7-phthalazinyl, 1-methoxy-6-phthalazinyl, 1,4-dimethoxy-6-phthalazinyl, 1,8-naphthyridin-2-yl, 2-quinoxalinyl, 6- Quinoxalinyl, 2,3-dimethyl-6-quinoxalinyl, 2,3-dimethoxy-6-quinoxalinyl, 2-quinazolinyl, 7-quinazolinyl, 2-dimethylamino-6-quinazoli Nilyl, 3-cinnolinyl, 6-cinnolinyl, 7-cinnolinyl, 3-methoxy-7-cinnolinyl, 2-phthyridinyl, 6-phthyridinyl, 7-phthyridinyl, 6 , 7-dime Cy-2-pteridinyl, 2-carbazolyl, 3-carbazolyl, 9-methyl-2-carbazolyl, 9-methyl-3-carbazolyl, β-carbolin-3-yl, 1 -Methyl-β-carbolin-3-yl, 1-methyl-β-carbolyl-6-yl, 3-phenantridinyl, 2-acridinyl, 3-acridinyl, 2-ferimidinyl, 1 -Methyl-5-ferimidinyl, 5-phenanthrolinyl, 6-phenanthrolinyl, 1-phenazinyl, 2-phenazinyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2 -Phenothiazinyl, 3-phenothiazinyl, 10-methyl-3-phenothiazinyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 4-methyl-3-furazanyl, 2- Phenoxazinyl or 10-methyl-2-phenoxazinyl.
    Naphthyl unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 -alkylthio, hydroxy, phenylamino or di (C 1 -C 4 alkyl) amino, Phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo- [b] thienyl, naph Tol [2,3-b] thienyl, thiarenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxatiinyl, pyrrolyl, isoindoleyl, indolyl, phenothiazinyl, biphenyl, terphenyl , Fluorenyl or phenoxazinyl such as 1-naphthyl, 2-naphthyl, 1-phenylamino-4-naphthyl, 1-methylnaphthyl, 2-methylnaphthyl, 1-methoxy-2-naph Methyl, 2-methoxy-1-naphthyl, 1-dimethylamino-2-naphthyl, 1,2-dimethyl-4-naphthyl, 1,2-dimethyl-6-naphthyl, 1,2-dimethyl- 7-naphthyl, 1,3-dimethyl-6-naphthyl, 1,4-dimethyl-6-naphthyl, 1,5-dimethyl-2-naphthyl, 1,6-dimethyl-2-naphthyl, 1 -Hydroxy-2-naphthyl, 2-hydroxy-1-naphthyl, 1,4-dihi Roxy-2-naphthyl, 7-phenanthryl, 1-anthryl, 2-anthryl, 9-anthryl, 3-benzo [b] thienyl, 5-benzo [b] thienyl, 2-benzo [b ] Thienyl, 4-dibenzofuryl, 4,7-dibenzofuryl, 4-methyl-7-dibenzofuryl, 2-xanthenyl, 8-methyl-2-xanthenyl, 3-xanthenyl, Particular preference is given to 2-pyrrolyl, 3-pyrrolyl, 2-phenothiazinyl, 3-phenothiazinyl, 10-methyl-3-phenothiazinyl.
    Halogen is typically chlorine, bromine or iodine. Chlorine is preferred.
    Alkanoyl of up to 25 carbon atoms is for example formyl, acetyl, propionyl, butanoyl, pentanoyl, hexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, trideca Branched or straight-chain radicals such as noyl, tetradecanoyl, pentadecanoyl, hexadecanoyl, heptadecanoyl, octadecanoyl, aicosanoyl or docosanoyl. Preference is given to alkanoyls of 2 to 18, in particular 2 to 12, such as 2 to 6 carbon atoms. Acetyl is particularly preferred.
    C 2 -C 25 alkanoyl substituted by a di (C 1 -C 6 alkyl) phosphonate group is, for example, (CH 3 CH 2 O) 2 POCH 2 CO—, (CH 3 O) 2 POCH 2 CO—, ( CH 3 CH 2 CH 2 CH 2 O) 2 POCH 2 CO-, (CH 3 CH 2 O) 2 POCH 2 CH 2 CO-, (CH 3 O) 2 POCH 2 CH 2 CO-, (CH 3 CH 2 CH 2 CH 2 O) 2 POCH 2 CH 2 CO-, (CH 3 CH 2 O) 2 PO (CH 2 ) 4 CO-, (CH 3 CH 2 O) 2 PO (CH 2 ) 8 CO- or (CH 3 CH 2 O) 2 PO (CH 2 ) 17 CO—.
    Alkanoyloxy of up to 25 carbon atoms is for example formyloxy, acetyloxy, propionyloxy, butanoyloxy, pentanoyloxy, hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy , Undecanoyloxy, dodecanoyloxy, tridecanoyloxy, tetradecanoyloxy, pentadecanoyloxy, hexadecanoyloxy, heptadecanoyloxy, octadecanoyloxy, icosananoyloxy or docosanoyloxy Branched or straight chain radicals such as; Preference is given to alkanoyloxy of 2 to 18, especially 2 to 12, such as 2 to 6 carbon atoms. Acetoxy is particularly preferred.
    3 to 25 alkenoyl include, for example, propenoyl, 2-butenoyl, 3-butenoyl, isobutenoyl, n-2,4-pentadienoyl, 3-methyl-2-butenoyl, n-2-octane Branched or straight-chain radicals such as noyl, n-2-dodecenoyl, isododecenoyl, oleoyl, n-2-octadecenoyl or n-4-octadecenoyl. 3 to 18, preferably 3 to 12, such as 3 to 6, particularly preferably 3 to 4 carbon atoms of alkenoyl.
    Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkenoyl comprising for example CH 3 OCH 2 CH 2 CH═CHCO— or CH 3 OCH 2 CH 2 OCH═CHCO—.
    Alkenoyloxy of 3 to 25 carbon atoms is typically propenoyloxy, 2-butenoyloxy, 3-butenoyloxy, isobutenoyloxy, n-2,4-pentadienoyloxy, 3-methyl-2 Butenoyloxy, n-2-octenoyloxy, n-2-dodecenoyloxy, isododecenoyloxy, oleoyloxy, n-2-octadecenoyloxy or n-4-octadecenoyl Branched or straight chain radicals such as oxy. 3 to 18, preferably 3 to 12, such as 3 to 6, particularly preferably 3 to 4 carbon atoms of alkenoyloxy.
    Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkenoyloxy comprising is typically CH 3 OCH 2 CH 2 CH═CHCOO— or CH 3 OCH 2 CH 2 OCH═CHCOO—.
    Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkanoyl, which typically comprises CH 3 -O-CH 2 CO-, CH 3 -S-CH 2 CO-, CH 3 -NH-CH 2 CO-, CH 3 -N (CH 3 ) -CH 2 CO-, CH 3 -O-CH 2 CH 2 -O-CH 2 CO-, CH 3- (O-CH 2 CH 2- ) 2 O-CH 2 -CO-, CH 3- (O —CH 2 —CH 2 —) 3 O—CH 2 CO— or CH 3 — (O—CH 2 CH 2 —) 4 O—CH 2 CO—.
    Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkanoyloxy comprising typically is CH 3 -O-CH 2 COO-, CH 3 -S-CH 2 COO-, CH 3 -NH-CH 2 COO-, CH 3 -N (CH 3 ) -CH 2 COO-, CH 3 -O-CH 2 CH 2 -O-CH 2 COO-, CH 3- (O-CH 2 CH 2- ) 2 O-CH 2 -COO-, CH 3- ( O-CH 2 CH 2- ) 3 O-CH 2 COO- or CH 3- (O-CH 2 CH 2- ) 4 O-CH 2 COO-.
    C 6 -C 9 cycloalkylcarbonyl is typically cyclohexylcarbonyl, cycloheptylcarbonyl or cyclooctylcarbonyl. Cyclohexylcarbonyl is preferred.
    C 6 -C 9 -cycloalkylcarbonyloxy is, for example, cyclohexylcarbonyloxy, cycloheptylcarbonyloxy or cyclooctylcarbonyloxy. Cyclohexylcarbonyloxy is preferred.
    Preferably C 1 -C 12 alkyl-substituted benzoyl comprising 1 to 3, more preferably 1 or 2 alkyl groups is o-, m- or p-methylbenzoyl, 2,3-dimethylbenzoyl, 2 , 4-dimethylbenzoyl, 2,5-dimethylbenzoyl, 2,6-dimethylbenzoyl, 3,4-dimethylbenzoyl, 3,5-dimethylbenzoyl, 2-methyl-6-ethylbenzoyl, 4-tert-butylbenzoyl, 2 Ethylbenzoyl, 2,4,6-trimethylbenzoyl, 2,6-dimethyl-4-tert-butylbenzoyl or 3,5-di-tert-butylbenzoyl. Preferred substituents are C 1 -C 8 -alkyl, in particular C 1 -C 4 -alkyl.
    C 1 -C 12 alkyl-substituted benzoyloxy, which preferably comprises 1 to 3, more preferably 1 or 2 alkyl groups, is for example o-, m- or p-methylbenzoyloxy, 2,3-dimethyl Benzoyloxy, 2,4-dimethylbenzoyloxy, 2,5-dimethylbenzoyloxy, 2,6-dimethylbenzoyloxy, 3,4-dimethylbenzoyloxy, 3,5-dimethylbenzoyloxy, 2-methyl-6-ethyl Benzoyloxy, 4-tert-butylbenzoyloxy, 2-ethylbenzoyloxy, 2,4,6-trimethylbenzoyloxy, 2,6-dimethyl-4-tert-butylbenzoyloxy or 3,5-di-tert-butylbenzoyloxy . Preferred substituents are C 1 -C 8 -alkyl, especially C 1 -C 4 alkyl.
    Alkyl of up to 25 carbon atoms is methyl, ethyl, propyl, isopropyl, n-butyl, secondary butyl, isobutyl, tertiary butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3 -Dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl , 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5- It is a branched or straight chain radical such as hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, icosyl or docosyl. Preferred ones of R 2 and R 4 are eg C 1 -C 18 -alkyl. Particularly preferred R 4 is C 1 -C 4 alkyl.
    Alkenyl of 3 to 25 carbon atoms is propenyl, 2-butenyl, 3-butenyl, isobutenyl, n-2,4-pentadienyl, 3-methyl-2-butenyl, n-2-octenyl and branched or straight chain radicals such as n-2-dodecenyl, isododecenyl, oleyl, n-2-octadecenyl or n-4-octadecenyl. Alkenyl of 3 to 18, preferably 3 to 12, such as 3 to 6, especially 3 to 4 carbon atoms.
    Alkenyloxy of 3 to 25 carbon atoms includes propenyloxy, 2-butenyloxy, 3-butenyloxy, isobutenyloxy, n-2,4-pentadienyloxy, 3-methyl-2-butenyloxy branched or straight chains such as n-2-octenyloxy, n-2-dodecenyloxy, isododecenyloxy, oleyloxy, n-2-octadecenyloxy or n-4-octadecenyloxy It is a radical. Alkenyloxy of 3 to 18, preferably 3 to 12, such as 3 to 6, especially 3 to 4 carbon atoms.
    Alkynyl of 3 to 25 carbon atoms is branched, such as propynyl (-CH 2 -C≡CH), 2-butynyl, 3-butynyl, n-2-octynyl or n-2-dodecynyl, or It is a straight chain radical. Alkynyl of 3 to 18, preferably 3 to 12, such as 3 to 6, especially 3 to 4 carbon atoms.
    Alkynyloxy of 3 to 25 carbon atoms is for example propynyloxy (-OCH 2 -C -CH), 2-butynyloxy, 3-butynyloxy, n-2-octynyloxy or n-2-dodec Branched or straight-chain radicals such as niloxy. Alkynyloxy of 3 to 18, preferably 3 to 12, such as 3 to 6, especially 3 to 4 carbon atoms.
    Oxygen, sulfur or in the middle of the chain C 2 -C 25 alkyl comprising, for example, CH 3 —O—CH 2 —, CH 3 —S—CH 2 —, CH 3 —NH—CH 2 —, CH 3 —N (CH 3 ) —CH 2 − , CH 3 -O-CH 2 -CH 2 -O-CH 2- , CH 3- (O-CH 2 CH 2- ) 2 O-CH 2- , CH 3- (O-CH 2 CH 2- ) 3 O-CH 2 -or CH 3- (O-CH 2 CH 2- ) 4 O-CH 2- .
    C 7 -C 9 phenylalkyl is typically benzyl, α-methylbenzyl, α, α-dimethylbenzyl or 2-phenyl-ethyl. Preference is given to benzyl and α, α-dimethylbenzyl.
    C 7 -C 9 phenylalkyl unsubstituted on phenyl or substituted by one to three C 1 -C 4 alkyls is for example benzyl, α-methylbenzyl, α, α-dimethylbenzyl, 2-phenylethyl, 2- Methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2,4-dimethylbenzyl, 2,6-dimethylbenzyl or 4-tert-butylbenzyl. Benzyl is preferred.
    Oxygen, sulfur or in the middle of the chain And C 7 -C 25 phenylalkyl which is unsubstituted or substituted by 1 to 3 C 1 -C 4 alkyl on phenyl is for example phenoxymethyl, 2-methylphenoxymethyl, 3-methyl-phenoxy Methyl, 4-methylphenoxymethyl, 2,4-dimethylphenoxymethyl, 2,3-dimethyl-phenoxymethyl, phenylthiomethyl, N-methyl-N-phenylmethyl, N-ethyl-N-phenylmethyl, 4-tert-butylphenoxymethyl, 4-tert-butylphenoxyethoxymethyl, 2,4-di-tert-butyl phenoxymethyl, 2,4-di-tert-butylphenoxyethoxymethyl, phenoxyethoxyethoxy Branched or straight-chain radicals such as ethoxymethyl, benzyloxymethyl, benzyloxyethoxymethyl, N-benzyl-N-ethylmethyl or N-benzyl-N-isopropylmethyl.
    C 7 -C 9 phenylalkoxy is typically benzyloxy, α-methylbenzyloxy, α, α-dimethylbenzyloxy or 2-phenylethoxy. Benzyloxy is preferred.
    Preferably C 1 -C 4 alkyl-substituted phenyls containing 1 to 3, in particular 1 or 2 alkyl groups are typically o-, m- or p-methylphenyl, 2,3-dimethylphenyl, 2,4 -Dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2-methyl-6-ethylphenyl, 4-tert-butylphenyl, 2-ethyl Phenyl or 2,6-diethylphenyl.
    Preferably C 1 -C 4 alkyl-substituted phenoxy comprising 1 to 3, especially 1 or 2 alkyl groups is typically o-, m- or p-methylphenoxy, 2,3-dimethylphenoxy , 2,4-dimethylphenoxy, 2,5-dimethylphenoxy, 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3,5-dimethylphenoxy, 2-methyl-6-ethylphenoxy , 4-tert-butylphenoxy, 2-ethylphenoxy or 2,6-diethylphenoxy.
    Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkyl is for example cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, tert-butyl Cyclohexyl, cycloheptyl or cyclooctyl. Cyclohexyl and tert-butylcyclohexyl are preferred.
    Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkoxy is for example cyclopentoxy, methylcyclopentoxy, dimethylcyclopentoxy, cyclohexoxy, methylcyclohexoxy, dimethylcyclohexoxy, Trimethylcyclohexoxy, tert-butylcyclohexoxy, cycloheptoxy or cyclooctoxy. Cyclohexoxy and tert-butylcyclohexoxy are preferred.
    Alkoxy of up to 25 carbon atoms is for example methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, Branched or straight chain radicals such as tetradecyloxy, hexadecyloxy or octadecyloxy. Preference is given to alkoxy of 1 to 12, especially 1 to 8, such as 1 to 6 carbon atoms.
    Oxygen, sulfur or in the middle of the chain C 2 -C 25 alkoxy comprising CH 3 -O-CH 2 CH 2 O-, CH 3 -S-CH 2 CH 2 O-, CH 3 -NH-CH 2 CH 2 O-, CH 3- N (CH 3 ) -CH 2 CH 2 O-, CH 3 -O-CH 2 -CH 2 -O-CH 2 CH 2 O-, CH 3- (O-CH 2 CH 2- ) 2 O-CH 2 CH 2 O—, CH 3 — (O—CH 2 CH 2 —) 3 O—CH 2 CH 2 O— or CH 3 — (O—CH 2 CH 2 —) 4 O—CH 2 CH 2 O—.
    Alkylthio of up to 25 carbon atoms is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, pentylthio, isopentylthio, hexylthio, heptylthio, octylthio, decylthio And branched or straight chain radicals such as tetradecylthio, hexadecylthio or octadecylthio. Preference is given to alkylthio of 1 to 12, in particular 1 to 8, such as 1 to 6 carbon atoms.
    Alkylamino of up to 4 carbon atoms is typically a branched or straight chain radical such as methylamino, ethylamino, propylamino, isopropylamino, n-butylamino, isobutylamino or tertiary butylamino.
    Di (C 1 -C 4 alkyl) amino is independently of the other two radicals, typically dimethylamino, methylethylamino, diethylamino, methyl-n-propylamino, methylisopropylamino, methyl-n-butylamino, Methylisobutylamino, ethylisopropylamino, ethyl-n-butylamino, ethylisobutylamino, ethyl-tertiarybutylamino, diethylamino, diisopropylamino, isopropyl-n-butylamino, isopropylisobutylamino Or branched or straight chain such as di-n-butylamino or diisobutylamino.
    Alkanoylamino of up to 25 carbon atoms is for example formylamino, acetylamino, propionylamino, butanoylamino, pentanoylamino, hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino , Undecanoylamino, dodecanoylamino, tridecanoylamino, tetradecanoylamino, pentadecanoylamino, hexadecanoylamino, heptadecanoylamino, octadecanoylamino, icosanoylamino or docosanoylamino Branched or straight chain radicals such as; Preference is given to alkanoylamino of 2 to 18, especially 2 to 12, such as 2 to 6 carbon atoms.
    C 1 -C 18 alkylene is typically branched or straight-chained, such as methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, decamethylene, dodecamethylene or octadecamethylene Is a radical. Preference is given to C 1 -C 12 alkylenes, in particular C 1 -C 8 alkylene.
    Preferably C 1 -C 4 alkyl-substituted C 5 -C 12 cycloalkylene rings containing 1 to 3, in particular 1 or 2 branched or straight chain alkyl groups are for example cyclopentylene, methylcyclopentylene , Dimethylcyclopentylene, cyclohexylene, methylcyclohexylene, dimethylcyclohexylene, trimethylcyclohexylene, tert-butylcyclohexylene, cycloheptylene, cyclooctylene or cyclodecylene. Cyclohexylene and tert-butylcyclohexylene are preferred.
    Oxygen, sulfur or in the middle of the chain C 2 -C 18 alkylene comprising, for example, —CH 2 —O—CH 2 —, —CH 2 —S—CH 2 —, —CH 2 —NH—CH 2 —, —CH 2 —N (CH 3 ) -CH 2- , -CH 2 -O-CH 2 -CH 2 -O-CH 2- , -CH 2- (O-CH 2 CH 2- ) 2 O-CH 2- , -CH 2- (O -CH 2 CH 2- ) 3 O-CH 2- , -CH 2- (O-CH 2 CH 2- ) 4 O-CH 2 -or -CH 2 CH 2 -S-CH 2 CH 2- .
    C 2 -C 18 alkenylene is for example vinylene, methylvinylene, octenylethylene or dodecenylethylene. Preference is given to C 2 -C 8 alkenylene.
    Alkylidene of 2 to 20 carbon atoms is typically ethylidene, propylidene, butylidene, pentidene, 4-methylpentylidene, heptylidene, nonylidene, tridecylidene, nonadesylidene, 1-methylethylidene, 1-ethylpropylidene or 1-ethylpentylidene. C 2 -C 8 alkylidene is preferred.
    Phenylalkylidene of 7 to 20 carbon atoms is, for example, benzylidene, 2-phenylethylidene or 1-phenyl-2-hexylidene. Preference is given to C 7 -C 9 phenylalkylidene.
    C 5 -C 8 cycloalkylene is a saturated hydrocarbon group having two free valences and one or more ring units and typically is cyclopentylene, cyclohexylene, cycloheptylene or cyclooctylene. Cyclohexylene is preferred.
    C 7 -C 8 bicycloalkylene is typically bicycloheptylene or bicyclooctylene.
    Unsubstituted or C 1 -C 4 -alkyl-substituted phenylene or naphthylene is typically 1,2-, 1,3-, 1,4-phenylene, 1,2-, 1,3-, 1 , 4-, 1,6-, 1,7-, 2,6- or 2,7-naphthylene. 1,4-phenylene is preferred.
    Preferably C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkylidene rings containing 1 to 3, in particular 1 or 2 branched or straight chain alkyl groups are typically cyclopentylidene, methylcyclo Pentylidene, dimethylcyclopentylidene, cyclohexylidene, methylcyclohexylidene, dimethylcyclohexylidene, trimethylcyclohexylidene, tert-butylcyclohexylidene, cycloheptidene or cyclooctylidene . Cyclohexylidene and tert-butylcyclohexylidene are preferred.
    The 1-, 2- or 3-valent metal cations are preferably alkali metal cations, alkaline earth metal cations or aluminum cations, typically Na + , K + , Mg ++ , Ca ++ or Al +++ .
    Important compositions include phenyl when n is 1, R 1 is unsubstituted or substituted in the para position by C 1 -C 18 alkylthio, di (C 1 -C 4 alkyl) amino; 1- to 5-substituted alkylphenyls having up to 18 carbon atoms in total from 1 to 5 alkyl substituents; Naphthyl, biphenyl, terphenyl, phenanthryl, anthryl unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, hydroxy or amino Containing as component (b) at least one compound of formula (1) which is fluorenyl, carbazolyl, thienyl, pyrrolyl, phenothiazinyl or 5,6,7,8-tetrahydronaphthyl.
    if n is 2,
    R 1 is -R 12 -XR 13- ,
    R 12 and R 13 are phenylene,
    X is oxygen or -NR 31- , and
    Preferred are compositions comprising as component (b) at least one compound of the formula (1) wherein R 31 is C 1 -C 4 alkyl.
    Also preferred are compositions containing as component (b) one or more compounds of formula (1):
    If n is 1,
    R 1 is unsubstituted or C 1 -C 4 alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 alkylthio, hydroxy, halogen, amino, C 1 -C 4 alkylamino or di (C 1- Naphthyl, phenanthryl, thienyl, dibenzofuryl, carbazolyl, fluorenyl or a radical of formula (2) substituted by C 4 alkyl) amino,
    (2)
    R 7 , R 8 , R 9 , R 10 and R 11 independently of one another are hydrogen, chlorine, bromine, hydroxy, C 1 -C 18 alkyl; C 2 -C 18 alkyl comprising oxygen or sulfur in the middle of the chain; C 1 -C 18 alkoxy; C 2 -C 18 -alkoxy containing oxygen or sulfur in the middle of the chain; C 1 -C 18 alkylthio, C 3 -C 12 alkenyloxy, C 3 -C 12 alkynyloxy, C 7 -C 9 phenylalkyl, C 7 -C 9 phenylalkoxy, unsubstituted or C 1 -C 4 alkyl-substituted phenyl; Phenoxy, cyclohexyl, C 5 -C 8 cycloalkoxy, C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl) amino, C 1 -C 12 -alkanoyl, containing oxygen or sulfur in the middle of the chain C 3 -C 12 alkanoyl; C 1 -C 12 alkanoyloxy, C 3 -C 12 -alkanoyloxy comprising oxygen or sulfur in the middle of the chain; C 1 -C 12 alkanoylamino, C 3 -C 12 alkenoyl, C 3 -C 12 alkenoyloxy, cyclohexylcarbonyl, cyclohexylcarbonyloxy, benzoyl or C 1 -C 4 -alkyl-substituted benzoyl ; Benzoyloxy or C 1 -C 4 alkyl-substituted benzoyloxy; or Or, in formula (2), R 7 and R 8 , or R 8 and R 11 combine with a linking carbon atom to form a benzo ring,
    R 15 is hydroxy, C 1 -C 12 alkoxy or ,
    R 18 and R 19 are independently of each other hydrogen, C 1 -C 4 alkyl,
    R 20 is hydrogen,
    R 21 is hydrogen, phenyl, C 1 -C 18 alkyl, C 2 -C 18 alkyl comprising oxygen or sulfur in the middle of the chain; C 7 -C 9 phenylalkyl; C 7 -C 18 phenylalkyl which contains oxygen or sulfur in the chain and is unsubstituted on phenyl or substituted by 1 to 3 C 1 -C 4 alkyl, or the radicals R 20 and R 21 are linked carbon atoms Combined with each other to form a cyclohexylene ring unsubstituted or substituted by 1 to 3 C 1 -C 4 alkyl;
    R 22 is hydrogen or C 1 -C 4 alkyl,
    R 23 is hydrogen, C 1 -C 18 alkanoyl, C 3 -C 18 alkenoyl, C 3 -C 12 alkanoyl including oxygen or sulfur in the middle of the chain; C 2 -C 12 alkanoyl substituted by di (C 1 -C 6 alkyl) phosphonate groups; C 6 -C 9 cycloalkylcarbonyl, benzoyl,
    or ego,
    R 24 and R 25 are independently of each other hydrogen or C 1 -C 12 alkyl,
    R 26 is hydrogen or C 1 -C 4 alkyl,
    R 27 is C 1 -C 12 alkylene, C 2 -C 8 alkenylene, C 2 -C 8 alkylidene, C 7 -C 12 phenylalkylidene, C 5 -C 8 cycloalkylene or phenylene,
    R 28 is hydroxy, C 1 -C 12 alkoxy or ego,
    R 29 is oxygen or -NH-,
    R 30 is C 1 -C 18 alkyl or phenyl, and
    s is 1 or 2.
    Preferred are compositions containing as component (b) at least one compound of the formula (1):
    If n is 1,
    R 1 is phenanthryl, thienyl, dibenzofuryl, unsubstituted or C 1 -C 4 alkyl-substituted carbazolyl; Or fluorenyl; Or a radical of the formula (2)
    (2)
    R 7 , R 8 , R 9 , R 10 and R 11 independently of one another are hydrogen, chlorine, hydroxy, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 3- C 4 alkenyloxy, C 3 -C 4 alkynyloxy, phenyl, benzoyl, benzoyloxy or ,
    R 20 is hydrogen,
    R 21 is hydrogen, phenyl or C 1 -C 18 alkyl, or the radicals R 20 and R 21 in combination with a linking carbon atom are unsubstituted or substituted by 1 to 3 C 1 -C 4 alkyl cyclohexylene rings Form the
    R 22 is hydrogen or C 1 -C 4 alkyl, and
    R 23 is hydrogen, C 1 -C 12 alkanoyl or benzoyl.
    when n is 1, at least one of formula (1) wherein R 7 , R 8 , R 9 , R 10 and R 11 are independently of each other hydrogen, C 1 -C 12 alkyl, C 1 -C 4 -alkylthio or phenyl; Particular preference is given to compositions containing the compound as component (b).
    Of particular interest are compositions containing as component (b) one or more compounds of the formula (1):
    R 2 , R 3 , R 4 and R 5 independently of one another are hydrogen, chlorine, C 1 -C 18 alkyl, benzyl, phenyl, C 5 -C 8 cycloalkyl, C 1 -C 18 alkoxy, C 1 -C 18 Alkylthio, C 1 -C 18 alkanoyloxy, C 1 -C 18 -alkanoylamino, C 3 -C 18 alkenoyloxy or benzoyloxy; Or R 2 and R 3 , or R 3 and R 4 , or R 4 and R 5 combine with the linking carbon atom to form a benzo ring or R 4 is additionally-(CH 2 ) p -COR 15 or-(CH 2 ) q OH, or if R 3 , R 5 and R 6 are hydrogen, R 4 is additionally a radical of formula (3),
    R 15 is hydroxy, C 1 -C 12 alkoxy or ego,
    R 16 and R 17 are methyl groups or combine with a linking carbon atom to form a C 5 -C 8 cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C 1 -C 4 alkyl;
    R 24 and R 25 are independently of each other hydrogen or C 1 -C 12 alkyl,
    p is 1 or 2, and
    q is 2, 3, 4, 5 or 6.
    Also of particular interest are compositions comprising as component (b) one or more compounds of formula (1) wherein at least two R 2 , R 3 , R 4 and R 5 are hydrogen.
    Of particular interest are compositions comprising as component (b) at least one compound of the formula (1) in which R 3 and R 5 are hydrogen.
    Very particularly important powder coating compositions are
    R 2 is C 1 -C 4 alkyl,
    R 3 is hydrogen,
    R 4 is C 1 -C 4 alkyl, or if R 6 is hydrogen, R 4 is additionally a radical of formula (3),
    R 5 is hydrogen,
    R 16 and R 17 contain one or more compounds of formula (1) which, in combination with a linking carbon atom, form a cyclohexylidene ring.
    The following compounds are examples of the benzofuran-2-one type which are particularly suitable as component (b) in the novel composition: 3- [4- (2-acetoxyethoxy) phenyl] -5,7-di-tert-butylbenzofuran 2-one; 5,7-di-tert-butyl-3- [4- (2-stearoyloxyethoxy) phenyl] benzofuran-2-one; 3,3'-bis [5,7-di-tert-butyl-3- (4- [2-hydroxy-ethoxy] phenyl) -benzofuran-2-one]; 5,7-di-tert-butyl-3- (4-ethoxyphenyl) benzofuran-2-one; 3- (4-acetoxy-3,5-dimethylphenyl) -5,7-di-tert-butylbenzofuran-2-one; 3- (3,5-dimethyl-4-pivaloyloxyphenyl) -5,7-di-tert-butylbenzofuran-2-one; 5,7-di-tert-butyl-3-phenylbenzofuran-2-one; 5,7-di-tert-butyl-3- (3,4-dimethylphenyl) benzofuran-3-one; 5,7-di-tert-butyl-3- (2,3-dimethylphenyl) benzofuran-2-one.
    Also of particular interest are compositions containing as component (b) one or more compounds of formula (5):
    Where
    R 2 is hydrogen or C 1 -C 6 alkyl,
    R 3 is hydrogen,
    R 4 is hydrogen or C 1 -C 6 alkyl,
    R 5 is hydrogen,
    R 7 , R 8 , R 9 , R 10 and R 11 independently of one another are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or Provided that at least two R 7 , R 8 , R 9 , R 10 and R 11 are hydrogen;
    R 20 , R 21 and R 22 are hydrogen, and
    R 23 is C 2 -C 4 alkanoyl.
    Very particular preference is given to compositions comprising as component (b) one or more of the following formulas (5a) or (5b) or mixtures thereof:

    Compounds of the benzofuran-2-one type used as component (b) in the novel compositions are known in the literature and their preparation is described, for example, in US Pat. 4,325,863; U.S. 4,388,244; U.S. 5,175,312; U.S. 5,252,643; U.S. 5,216,052; U.S. 5,369,159; U.S. 5,488,117; U.S. 5,356,966; U.S. 5,367,008; U.S. 5,428,162; U.S. 5,428,177 or U.S. 5,516,920.
    Compounds of benzofuran-2-one type [component (b)] are suitable for stabilizing polycarbonates, polyesters or polyketones or mixtures or combinations thereof from degradation by oxidation, heat and / or photoinduction. It is particularly important that compounds of the benzofuran-2-one type do not substantially reduce the transparency of the plastics and substantially prevent sulfidation when exposed to light or under oxidation or thermal stress.
    It is also preferred that these novel compositions are solid solids and glassy shaped articles in which component (a) is transparent.
    Glassy molded articles are, for example, windows, windshields, automotive glass, protective films or packaging such as bottles or films.
    Particularly important compositions are those in which the shaped article used as component (a) is transparent at wavelengths 350 to 700 nm.
    Polyesters (PES) can be homo- or copolyesters composed of aliphatic, cycloaliphatic or aromatic dicarboxylic acids and diols or hydroxycarboxylic acids.
    Aliphatic dicarboxylic acid may contain 2 to 40 carbon atoms, alicyclic dicarboxylic acid may contain 6 to 10 carbon atoms, aromatic dicarboxylic acid may contain 8 to 14 carbon atoms, and aliphatic hydroxycarboxylic acid Silver may contain 2 to 12 carbon atoms, and alicyclic as well as alicyclic hydroxycarboxylic acids may contain 7 to 14 carbon atoms.
    Aliphatic diols may contain 2 to 12 carbon atoms, alicyclic diols may contain 5 to 8 carbon atoms, and aromatic diols may contain 6 to 16 carbon atoms.
    Aromatic diols are those in which two hydroxy groups are bonded to one or different aromatic hydrocarbon radicals.
    In addition, the polyester may be a bifunctional or higher monomer (e.g. pentaerythritol, trimellitic acid, 1,3,5-tri (hydroxyphenyl) benzene, 2,4-dihydroxybenzoic acid or 2 based on the dicarboxylic acid present) -(4-hydroxyphenyl) -2- (2,4-dihydroxyphenyl) propane) may be branched in small amounts from 0.1 to 3 mole percent.
    Polyesters composed of two or more monomers may be randomly arranged or may be block copolymers.
    Suitable dicarboxylic acids are straight and branched saturated aliphatic dicarboxylic acids, aromatic dicarboxylic acids, and cycloaliphatic dicarboxylic acids.
    Aliphatic dicarboxylic acids suitably have from 2 to 40 carbon atoms, typically oxalic acid, malonic acid, dimethylmalonic acid, succinic acid, pimelic acid, adipic acid, trimethyladipic acid, sebacic acid, azelaic acid and dimeric acids (with oleic acid and Dimerization products of unsaturated aliphatic carboxylic acids), succinic acids such as alkylated malonic acid and octadecylsuccinic acid.
    Suitable alicyclic dicarboxylic acids are: 1,3-cyclobutanedicarboxylic acid, 1,3-cyclopentanedicarboxylic acid, 1,3- and 1,4-cyclohexanedicarboxylic acid, 1,3- and 1,4- (di Carboxymethyl) cyclohexane, 4,4'-dicyclohexyldicarboxylic acid.
    Suitable aromatic dicarboxylic acids are: preferably 1,3-, 1,4-, 2,6- or 2,7-naphthalenedicarboxylic acid, 4,4'-diphenyldi, as well as terephthalic acid, isophthalic acid, o-phthalic acid Carboxylic acid, 4,4'-diphenylsulfondicarboxylic acid, 4,4'-benzophenonedicarboxylic acid, 1,1,3-trimethyl-5-carboxy-3- (p-carboxyphenyl) indane, 4,4'- Diphenyl ether dicarboxylic acid, bis-p- (carboxyphenyl) methane, or bis-p (carboxyphenyl) ethane.
    Aromatic dicarboxylic acids are preferred, and among these, terephthalic acid, isophthalic acid and 2,6-naphthalenedicarboxylic acid are particularly preferable.
    Other suitable dicarboxylic acids are those containing a -CO-NH- group; These are disclosed in DE-A-2 414 349. Dicarboxylic acids containing N-heterocyclic rings such as carboxyalkylated, carboxyphenylated or carboxybenzylated monoamine-s-triazinedicarboxylic acids (see DE-A-2 121 184), mono- or bishydantoin, halogenated Also suitable are benzimidazoles, or those derived from parabanic acid. In this case the carboxyalkyl group may contain 3 to 20 carbon atoms.
    Suitable aliphatic diols are linear and branched aliphatic glycols of 2 to 12, preferably 2 to 6 carbon atoms in the molecule, such as: ethylene glycol, 1,2- and 1,3-propylene glycol, 1,2-, 1 Preference is given to, 3-, 2,3- or 1,4-butanediol, pentyl glycol, neopentyl glycol, 1,6-hexanediol, 1,12-dodecanediol. Suitable alicyclic diols are, for example, 1,4-dihydroxycyclohexane. Other suitable aliphatic diols are typically 1,4-bis (hydroxymethyl) cyclohexane, aromatic-aliphatic diols (such as p-xylene glycol or 2,5-dichloro-p-xylene glycol), 2,2- (β -Hydroxyethoxyphenyl) propane as well as polyoxyalkylene glycols such as diethylene glycol, triethylene glycol, polyethylene glycol or polypropylene glycol. The alkylenediol is preferably straight chain and preferably contains 2 to 4 carbon atoms.
    Preferred diols are alkylenediol, 1,4-dihydroxycyclohexane and 1,4-bis (hydroxymethyl) cyclohexane. Particular preference is given to ethylene glycol, 1,4-butanediol as well as 1,2- and 1,3-propylene glycol.
    Other suitable aliphatic diols are β-hydroxyalkylated bis, preferably β-hydroxyethylated bisphenols such as 2,2-bis [4 '-(β-hydroxyethoxy) phenyl] propane. Other bisphenols are described later.
    Another group of suitable aliphatic diols are the heterocyclic diols disclosed in German documents 1 812 003, 2 342 432, 2 342 372 and 2 453 326. Detailed examples are: N, N'-bis (β-hydroxyethyl) -5,5-dimethylhydantoin, N, N'-bis (β-hydroxypropyl) -5,5-dimethylhydantoin, methylenebis [N- (β-hydroxyethyl) -5-methyl-5-ethylhydantoin], methylenebis [N- (β-hydroxyethyl) -5,5-dimethylhydantoin], N, N'-bis (β-hydroxyethyl) benzimidazolone, N, N'-bis (β-hydroxyethyl)-(tetrachloro) benzimidazolone, or N, N'-bis (β-hydroxyethyl)- (Tetrabromo) benzimidazolone.
    Suitable aromatic diols are monoatomic diphenols containing one hydroxy group in each aromatic and are preferably diatomic diphenols. Aromatic preferably means aromatic hydrocarbon radicals such as phenylene or naphthalene. Particular mention is made of the bisphenols described in the following formulae besides, for example, hydroquinone, resorcinol or 1,5-, 2,6- and 2,7-dihydroxynaphthalene:
    The hydroxy group is at the m-position, preferably the p-position, wherein R 'and R are alkyl having from 1 to 6 carbon atoms, halogen such as chlorine or bromine, and preferably hydrogen atoms. A is a direct bond, or oxygen, sulfur, -SO-, -SO 2- , , -P (O) (C 1 -C 20 alkyl)-, unsubstituted or substituted alkylidene, cycloalkylidene or alkylene.
    Typical examples of unsubstituted or substituted alkylidene are ethylidene, 1,1- or 2,2-propylidene, 2,2-butylidene, 1,1-isobutylidene, pentylidene, hexylidene , Heptylidene, octylidene, dichloroethylidene and trichloroethylidene.
    Typical examples of unsubstituted or substituted alkylene are methylene, ethylene, phenylmethylene, diphenylmethylene, methylphenylmethylene. Typical examples of cycloalkylidene are cyclopentylidene, cyclohexylidene, cycloheptylidene and cyclooctylidene.
    Specific examples of bisphenols include: bis (p-hydroxyphenyl) ether or bis (p-hydroxyphenyl) thioether, bis (p-hydroxyphenyl) sulfone, bis (p-hydroxyphenyl) methane, bis (4 -Hydroxyphenyl) -2,2'-biphenyl, phenylhydroquinone, 1,2-bis (p-hydroxyphenyl) ethane, 1-phenyl-bis (p-hydroxyphenyl) methane, diphenyl-bis ( p-hydroxyphenyl) methane, diphenyl-bis (p-hydroxyphenyl) ethane, bis (3,5-dimethyl-4-hydroxyphenyl) sulfone, bis (3,5-dimethyl-4-hydroxyphenyl ) -p-diisopropylbenzene, bis (3,5-dimethyl-4-hydroxyphenyl) -m-diisopropylbenzene, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propane , 1,1- or 2,2-bis (p-hydroxyphenyl) butane, 2,2-bis (p-hydroxyphenyl) hexafluoropropane, 1,1-dichloro- or 1,1,1- Tricyclo-2,2-bis (p-hydroxyphenyl) ethane, 1,1-bis (p-hydroxyphenyl) cyclopentane, and preferably 2,2-bis (p-hydroxyphenyl) propane (Bisphenol A) and 1,1-bis (p-hydroxyphenyl) cyclohexane (bisphenol C).
    Suitable polyesters of hydroxycarboxylic acids are typically polyesters of polycaprolactone, polypivalolactone or 4-hydroxycyclohexanecarboxylic acid or 4-hydroxybenzoic acid.
    Suitable polymers are also primarily polymers containing ester linkages, but may also contain other linkages such as, for example, polyester amides or polyester imides.
    Most important are polyesters containing aromatic dicarboxylic acids, especially polyalkylene terephthalates. Thus, in these novel molding compounds, the polyester is at least 30 mol%, preferably at least 40 mol%, at least 30 mol% of alkylenediol containing 2 to 12 carbon atoms, preferably at least 30 mol% of aromatic dicarboxylic acids based on the polyester. It is preferable that it consists of 40 mol% or more.
    In this case the alkylene diols are typically straight chains such as ethylene-, tri-, tetra- or hexamethylene glycol and preferably contain 2 to 6 carbon atoms, and are also aromatic dicarboxylic acid terephthalic acid and / or isophthalic acid.
    Particularly suitable polyesters are PEN, PTT, PET, PETG (glycol-modified polyethylene terephthalate) or PBT and their corresponding copolymers or combinations thereof. PET and its copolymers are particularly preferred.
    As esters of dicarboxylic acids, polycarbonate (PC) is the simplest polyester. Polycarbonates are usually obtained by condensation reactions of bisphenol A and phosgene or phosgene analogues such as trichloromethylchloroformate, triphosgene or diphenylcarbonate, in which case suitable transesterification catalysts such as hydrogenation Obtained by adding boron, such as amines such as 2-methylimidazole, or quaternary ammonium salts. In addition to bisphenol A, other bisphenol components may also be used, and also halogenated monomers may be used for the benzene molecule. Particularly suitable mentioned bisphenol components are: 2,2-bis (4'-hydroxyphenyl) propane (bisphenol A), 2,4'-di-hydroxydiphenylmethane, bis (2-hydroxyphenyl) methane, Bis (4-hydroxyphenyl) methane, bis (4-hydroxy-5-propylphenyl) methane, 1,1-bis (4'-hydroxyphenyl) ethane, bis (4-hydroxyphenyl) -cyclohexyl Methane, 2,2-bis (4'-hydroxyphenyl) -1-phenylpropane, 2,2-bis (3 ', 5'-dimethyl-4'-hydroxyphenyl) propane, 2,2-bis ( 3 ', 5'-dibromo-4'-hydroxyphenyl) propane, 2,2-bis (3', 5'-dichloro-4'-hydroxyphenyl) propane, 1,1-bis (4 ' -Hydroxyphenyl) cyclododecane, 1,1-bis (3 ', 5'-dimethyl-4'-hydroxyphenyl) cyclododecane, 1,1-bis (4'-hydroxyphenyl) -3, 3,5-trimethylcyclohexane, 1,1-bis (4'-hydroxyphenyl) -3,3,5,5-tetramethylcyclohexane or 1,1-bis (4'-hydroxyphenyl) -3 , 3,5-trimethylcyclopentane. The polycarbonates may be branched with an appropriate amount of bifunctional or higher monomers (examples described above).
    In addition to the combinations of PES and PC, in particular PBT / PC and PET / PC, for example the polymers to be used according to the invention are suitably PC / ABS and PBT / PC / ABS, PBT / PET / PC, PBT / PET / PC / ABS or Triple combinations, such as combinations of PBT / PC / ASA.
    The blend is prepared by conventional methods from the starting polymer. Preferred PES component is PBT and the preferred PC component is PC based on bisphenol A. Particular preference is given to the ratio of PES to PC in which one component is provided in at least 70% is preferably 95: 5 to 5:95.
    By transesterification, all PES / PC blends comprise a rather large block copolymer structure in which the blend portion is in the form of a PC / PES block copolymer. The physical property enhancement according to the present invention improves the compatibility between the polymers. However, so-called compatibilizers may also increase the compatibility. In this case, it may be for example a polyester / polycarbonate copolymer or a polyarylate (= aromatic polyester).
    Particularly important compositions are compositions wherein component (a) is a polycarbonate derived from bisphenol A.
    Polyketones are plastic materials prepared by polymerizing carbon monoxide and unsaturated hydrocarbons, in particular as disclosed in EP-A-0 222 454 or EP-A-0 685 517.
    As described above, there are compositions in which components (b) and (c) are present in an amount of 0.0005 to 5% by weight, preferably 0.001 to 2% by weight, typically 0.01 to 2% by weight, based on the weight of component (a) It is advantageous.
    In addition to components (a) and (b), the novel compositions may comprise additional additives or co-stabilizing agents, for example:
    1. Antioxidant
    1.1 alkylated monophenols such as 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2 , 6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2- (α -Methylcyclohexyl) -4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, 2,4,6-tricyclo-hexylphenol, 2,6-di-tert-butyl-4 Methoxymethylphenol, linear or branched nonylphenols such as 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1'-methylundes-1'-yl) Phenol, 2,4-dimethyl-6- (1'-methylheptades-1'-yl) phenol, 2,4-dimethyl-6- (1'-methyltrides-1'-yl) phenol and their mixture.
    1.2. Alkylthiomethylphenols such as 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol.
    1.3. Hydroquinones and alkylated hydroquinones such as 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl 4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxy Anisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis (3,5-di-tert-butyl-4-hydroxyphenyl) adipate.
    1.4. Tocopherols such as α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol and mixtures thereof (vitamin E)
    1.5. Hydroxylated thiodiphenyl ethers such as 2,2'-thiobis (6-tert-butyl-4-methylphenol), 2,2'-thiobis (4-octylphenol), 4,4'-thiobis (6-tert-butyl-3-methylphenol), 4,4'-thiobis- (6-tert-butyl-2-methylphenol), 4,4'-thiobis- (3,6-di-secondary Amylphenol), 4,4'-bis- (2,6-dimethyl-4-hydroxyphenyl) disulfide.
    1.6. Alkylidenebisphenols such as 2,2'-methylenebis (6-tert-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethylphenol), 2,2'- Methylenebis [4-methyl-6- (α-methylcyclohexyl) -phenol], 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis (6-nonyl 4-methylphenol), 2,2'-methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidenebis (4,6-di-tert-butylphenol), 2, 2'-ethylidenebis (6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis [6- (α-methylbenzyl) -4-nonylphenol], 2,2'-methylenebis [6- (α, α-dimethylbenzyl) -4-nonylphenol], 4,4'-methylenebis (2,6-di-tert-butylphenol), 4,4'-methylenebis (6-tert- Butyl-2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis (3-tert-butyl-5-methyl-2-hydrate Hydroxybenzyl) -4-methylphenol, 1,1,3-tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis (5-tert-butyl-4-hydroxy 2-methyl-phenyl) -3-n-dodecyl mercap Tobutane, ethylene glycol bis [3,3-bis (3'-tert-butyl-4'-hydroxyphenyl) butyrate], bis (3-tert-butyl-4-hydroxy-5-methylphenyl) dicyclopenta Dienes, 1,1-bis (3,5-dimethyl-2-hydroxyphenyl) butane, 2,2-bis (3,5-di-tert-butyl-4-hydroxyphenyl) propane, 2,2- Bis- (5-tert-butyl-4-hydroxy-2-methylphenyl) -4-n-dodecylmercaptobutane, 1,1,5,5-tetra- (5-tert-butyl-4-hydroxy -2-methylphenyl) pentane.
    1.7. O-, N- and S-benzyl compounds such as 3,5,3 ', 5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3, 5-dimethylbenzyl mercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzyl mercaptoacetate, tris (3,5-di-tert-butyl-4-hydroxybenzyl) amine, Bis (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3 , 5-di-tert-butyl-4-hydroxybenzylmercaptoacetate.
    1.8. Hydroxybenzylated malonates such as dioctadecyl-2,2-bis (3,5-di-tert-butyl-2-hydroxybenzyl) malonate, di-octadecyl-2- (3-tert-butyl -4-hydroxy-5-methylbenzyl) -malonate, di-dodecylmercaptoethyl-2,2-bis- (3,5-di-tert-butyl-4-hydroxybenzyl) malonate,
    1.9. Aromatic hydroxybenzyl compounds such as 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 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-hydroxybenzyl) phenol.
    1.10. Triazine compounds such as 2,4-bis (octylmercapto) -6- (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmer Capto-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-hydroxyphenoxy) -1,3,5-triazine, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy)- 1,2,3-triazine, 1,3,5-tris- (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tertiary -Butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenylethyl) -1,3, 5-triazine, 1,3,5-tris (3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate.
    1.11. Benzylphosphonates such as dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, di Octadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, 3,5-di Calcium salt of monoethyl ester of tert-butyl-4-hydroxybenzylphosphonic acid.
    1.12. Acylaminophenols such as 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N- (3,5-di-tert-butyl-4-hydroxyphenyl) carbamate.
    1.13. Mono or polyhydric alcohols such as 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-thiaundanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane and β- (3,5- Esters of di-tert-butyl-4-hydroxyphenyl) propionic acid.
    1.14. Mono or polyhydric alcohols such as 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) oxaamide, 3-thiaundanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane and β- (5-tertiary- Ester of butyl-4-hydroxy-3-methylphenyl) propionic acid.
    1.15. Monohydric or polyhydric alcohols such as 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-thiaundanol, 3-thiapentadecanol, Trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane and β- (3,5-dicyclohexyl-4-hydrate Oxyphenyl) propionic acid.
    1.16. Monohydric or polyhydric alcohols such as 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-thiaundanol, 3-thiapentadecanol, Trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane and 3,5-di-tert-butyl-4-hydroxy Esters of phenyl acetic acid.
    1.17. Amides of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid, such as N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexa Methylenediamine, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) trimethylenediamine, N, N'-bis (3,5-di-tert-butyl-4 Hydroxyphenylpropionyl) hydrazine.
    1.18. Ascorbic acid (vitamin C)
    1.19. Amine antioxidants such as N, N'-di-isopropyl-p-phenylenediamine, N, N'-di-secondary-butyl-p-phenylenediamine, N, N'-bis (1,4-dimethyl Pentyl) -p-phenylenediamine, N, N'-bis (1-ethyl-3-methylpentyl) -p-phenylenediamine, N, N'-bis (1-methylheptyl) -p-phenylenediamine , N, N'-dicyclohexyl-p-phenylenediamine, N, N'-diphenyl-p-phenylenediamine, N, N'-bis (2-naphthyl) -p-phenylenediamine, N -Isopropyl-N'-phenyl-p-phenylenediamine, N- (1,3-dimethylbutyl) -N'-phenyl-p-phenylenediamine, N- (1-methylheptyl) -N'-phenyl -p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4- (p-toluenesulfamoyl) -diphenylamine, N, N'-dimethyl-N, N'-di -Secondary-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N- (4-tert-octylphenyl ) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine such as p, p'-di-tert-octyldiphenylamine, 4-n-butyl Mino-phenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylaminophenol, bis (4-methoxyphenyl) amine, 2,6-di Tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N, N, N ', N'-tetramethyl-4,4 '-Diaminodiphenylmethane, 1,2-bis [(2-methylphenyl) amino] ethane, 1,2-di (phenylamino) propane, (o-tolyl) biguanide, bis [4- (1' , 3'-dimethylbutyl) phenyl] amine, tert-octylated N-phenyl-1-naphthylamine, mixture of mono- and dialkylated tert-butyl / tert-octyldiphenylamine, mono- and dialkylated nonyldi Mixtures of phenylamines, mixtures of mono- and dialkylated dodecyldiphenylamines, mixtures of mono- and dialkylated isopropyl / isohexyldiphenylamines, mixtures of mono- and dialkylated tert-butyldiphenylamines, 2,3 -Dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, mono- And mixtures of dialkylated tert-butyl / tert-octylphenothiazine, mixtures of mono- and dialkylated tert-octyl-phenothiazine, N-allylphenothiazine, N, N, N ', N'-tetraphenyl -1,4-diaminobut-2-ene, N, N-bis (2,2,6,6-tetramethyl-piperidin-4-yl-hexamethylenediamine, bis (2,2,6, 6-tetramethylpiperid-4-yl) sebacate, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidin-4-ol.
    2. UV absorbers and light stabilizers
    2.1. 2- (2'-hydroxyphenyl) benzotriazole such as 2- (2'-hydroxy-5'-methylphenyl) -benzotriazole, 2- (3 ', 5'-di-tert-butyl-2 '-Hydroxyphenyl) benzotriazole, 2- (5'-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-5'-(1,1,3, 3-tetramethylbutyl) phenyl) benzotriazole, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) -5-chloro-benzotriazole, 2- (3'-tertiary -Butyl-2'-hydroxy-5'-methylphenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-5'-tert-butyl-2'-hydroxyphenyl) benzotriazole , 2- (2'-hydroxy-4'-octyloxyphenyl) benzotriazole, 2- (3 ', 5'-di-tert-amyl-2'-hydroxyphenyl) benzotriazole, 2- ( 3 ', 5'-bis- (α, -α-dimethylbenzyl) -2'-hydroxyphenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5'-(2 -Methoxycarbonyl) phenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '-(2-octyloxycarbonylethyl) phenyl) benzotriazole, 2- (3 '-Dodecyl-2'-hydroxy -5'-methylphenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '-(2-isooctyloxycarbonylethyl) phenylbenzotriazole, 2,2'-methylene -Bis [4- (1,1,3,3-tetramethylbutyl) -6-benzotriazol-2-ylphenol] or 2- [3'-tert-butyl-5 '-(2-methoxy Transesterification product of carbonylethyl) -2'-hydroxyphenyl] -2H-benzotriazole with polyethylene glycol 300; [R-CH 2 CH 2- COO-CH 2 CH 2- ] 2 (R is 3 'Tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl),
    2,2, 2-hydroxybenzophenones such as 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2 ', 4 '-Trihydroxy and 2'-hydroxy-4,4'-dimethoxy derivatives.
    2.3. Esters of unsubstituted or substituted benzoic acids such as 4-tert-butyl-phenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis (4-tert-butyl-benzoyl) resorci Nol, Benzoyl Resorcinol, 2,4-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxy Benzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxy Benzoate.
    2.4. Acrylates such as ethyl α-cyano-β, β-diphenylacrylate, isooctyl α-cyano-β, β-diphenylacrylate, methyl α-carbomethoxycinnamate, methyl α-cyano- β-methyl-p-methoxy-cinnamate, butyl α-cyano-β-methyl-p-methoxy-cinnamate, methyl α-carbomethoxy-p-methoxy-cinnamate and N- (β- Carbomethoxy-β-cyanovinyl) -2-methylindolin.
    2.5 2,2'-thio-bis [4- (1,1,3,3- with optionally ligands such as n-butylamine, triethanolamine or N-cyclohexyl diethanolamine Tetramethylbutyl) phenol] nickel complex (such as 1: 1 or 1: 2 complex), nickel dibutyl dithiocarbamate, monoalkyl of 4-hydroxy-3,5-di-tert-butyl benzyl phosphonic acid Nickel salts of esters (such as methyl esters or ethyl esters), nickel complexes of ketoximes (such as 2-hydroxy-4-methylphenyl undecylketoxime), 1-phenyl-4-lauroyl, optionally with additional ligands Nickel complex of -5-hydroxypyrazole.
    2.6. Sterically hindered amines such as bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (2,2,6,6-tetramethyl-4-piperidyl) succinate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate, Bis (1,2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzyl malonate, 1- (2-hydroxy Condensation product of ethyl) -2,2,6,6-tetramethyl-4-hydroxypiperidine with succinic acid, N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl Condensation product of hexamethylenediamine with 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, tris (2,2,6,6-tetramethyl-4-piperidyl) nitrile Lotriacetate, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butane-tetracarboxylate, 1,1 '-(1,2-ethane Diyl) -bis- (3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-s Aryloxy-2,2,6,6-tetramethylpiperidine, 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decane-2, 4-dione, bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) Nate, N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine Linear or cyclic condensation products of 2-chloro-4,6-bis (4-n-butylamino-2,2,6,6-tetramethylpiperidyl) -1,3,5-triazine with 1, Condensation product of 2-bis (3-aminopropylamino) ethane, 2-chloro-4,6-di- (4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)- Condensation product of 1,3,5-triazine with 1,2-bis (3-aminopropylamino) ethane, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8 -Triazaspiro [4.5] decane-2,4-dione, 3-dodecyl-1- (2,2,6,6-tetramethyl-4-piperidyl) pyrrolidine-2,5-dione, 3-dodecyl-1- (1,2 , 2,6,6-pentamethyl-4-piperidyl) pyrrolidine-2,5-dione, 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethyl Mixtures of piperidine, N, N'-bis- (2,2,6,6-tetramethyl-4-piperidyl) hexamethyrenediamine and 4-cyclohexylamino-2,6-di-chloro- Condensation products of 1,3,5-triazine, 1,2-bis- (3-aminopropylamino) ethane and 2,4,6-trichloro-1,3,5-triazine as well as 4-butylamino Condensation products of -2,2,6,6-tetramethylpiperidine (CAS Reg. No. [136504-96-6]); N- (2,2,6,6-tetramethyl-4-piperidyl) -n-dodecylsuccinimide, N- (1,2,2,6,6-pentamethyl-4-piperidyl ) -n-dodecylsuccinimide, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro [4,5] decane, 7 , 7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospyro [4,5] decane with epichlorohydrin, product 1,1 ' -Bis (1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl) -2- (4-methoxyphenyl) ethene, N, N'-bis-formyl-N, N '-Bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine, 4-methoxy-methylene-malonic acid and 1,2,2,6,6-pentamethyl-4-hydride Diesters of oxypiperidine, poly [methylpropyl-3-oxy-4- (2,2,6,6-tetramethyl-4-piperidyl)] siloxane, malonic anhydride-α-olefin-copolymer And a reaction product of 2,2,6,6-tetramethyl-4-aminopiperidine or 1,2,2,6,6-pentamethyl-4-aminopiperidine.
    2.7. Oxamides such as 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanide, 2 , 2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N, N'-bis (3-dimethylaminopropyl) oxamide , 2-ethoxy-5-tert-butyl-2'-ethoxanilide and mixtures thereof with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide and o- and mixtures of p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides.
    2.8. 2- (2-hydroxyphenyl) -1,3,5-triazine such as 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine, 2 -(2-hydroxy-4-octyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2,4-dihydroxyphenyl)- 4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl ) -1,3,5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4,6-bis (4-methylphenyl) -1,3,5-triazine, 2- (2 -Hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-hexyloxy) phenyl-4,6-diphenyl-1,3 , 5-triazine, 2- (2-hydroxy-4-methoxyphenyl) -4,6-diphenyl-1,3,5-triazine, 2,4,6-tris [2-hydroxy- 4- (3-butoxy-2-hydroxy-propoxy) phenyl] -1,3,5-triazine, 2- (2-hydroxyphenyl) -4- (4-methoxyphenyl) -6- Phenyl-1,3,5-triazine,
    3. Metal deactivators such as N, N'-diphenyloxamide, N-salicyl-N'-salicyloyl hydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1,2,4-triazole, bis (benzylidene) oxalyl dihydrazide, oxanyl Reed, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N, N'-diacetyladifoyl dihydrazide, N, N'-bis (salicyloyl) oxalyl dihydrazide, N, N ' Bis (salicyloyl) thiopropionyl dihydrazide.
    4. Phosphites and phosphonites such as triphenyl phosphite, diphenyl alkyl phosphite, phenyl dialkyl phosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl Pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecyl pentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, Bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis (2,4-di-tert-butyl-6-methylphenyl) pentaeryte Lithol diphosphite, bis (2,4,6-tris (tert-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert-butylphenyl) 4,4 '-Biphenylene diphosphonite, 6-isooctyloxy-2,4,8,10- Tra-tert-butyl-12H-dibenz [d, g] -1,3,2-dioxaphosphosine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl- Dibenz [d, g] -1,3,2-dioxaphosphosine, bis (2,4-di-tert-butyl-6-methylphenyl) methyl phosphite, bis (2,4-di-tert-butyl -6-methylphenyl) ethylphosphite, 2-ethylhexyl (3,3 ', 5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite.
    Especially preferred are the following phosphites:
    Tris (2,4-di-tert-butylphenyl) phosphite (Irgafos R 168, Ciba-Geigy), tris (nonylphenyl) phosphite,

    Especially preferred are tris (2,4-di-tert-butylphenyl) phosphite [Irgafos R 168, Ciba Specialty Chemical Co.], bis (2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite [Irgafos R 38 , Ciba Specialty Chemicals, Formula (G)], Ultranox R 626 [GE Chemicals, Formula (D)], Tetrakis (2,4-di-tert-butylphenyl) -4,4'-biphenylene diphosphite Irgafos R P-EPQ, Ciba Specialty Chemicals, Formula (H), GSY R P101 [Yoshitomi, Formula (I)], Ultranox R 641 [GE Chemicals, Formula (K)], Doverphos R S9228 [Dover Chemicals, formula (L)] or Mark R HP10 [adeca argus, formula (M)].
    5. Hydroxyamines such as N, N-dibenzylhydroxyamine, N, N-diethylhydroxyamine, N, N-dioctylhydroxyamine, N, N-dilaurylhydroxyamine, N, N Ditetradecylhydroxyamine, N, N-dihexadecylhydroxyamine, N, N-dioctadecylhydroxyamine, N-hexadecyl-N-octadecylhydroxyamine, N-heptadecyl-N- Octadecylhydroxyamine, N, N-dialkylhydroxyamine derived from hydrogenated resin amine.
    6. Nitrons such as N-benzyl-alpha-phenyl nitron, N-ethyl-alpha-methyl nitron, N-octyl-alpha-heptyl nitron, N-lauryl-alpha-undecyl nitron, N- Tetradecyl-alpha-tridecyl-nitron, N-hexadecyl-alpha-pentadecyl nitron, N-octadecyl-alpha-heptadecyl nitron, N-hexadecyl-alpha-heptadecyl nitron, N-octa From decyl-alpha-pentadecyl nitron, N-heptadecyl-alpha-heptadecyl nitron, N-octadecyl-alpha-hexadecyl nitron, N, N'-dialkylhydroxyamine derived from hydrogenated resin amine Induced nitron.
    7. Thio synergists, such as dilauryl thiodipropionate or distearyl thiodipropionate.
    8. Peroxide degradants, such as esters of β-thiodipropionic acid, such as lauryl, stearyl, myristyl or tridecyl esters, zinc salts of mercaptobenzimidazole or 2-mercaptobenzimidazole, dibutyldithio Zinc carbamate, dioctadecyl disulfide, pentaerythritol tetrakis (β-dodecylmercapto) propionate.
    9. Basic co-stabilizers such as melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of high fatty acids, Such as calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate, potassium palmitate, antimony pyrocatechol or zinc pyrocatechol.
    109. Nucleating agents, for example inorganic materials such as talc, metal oxides such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of alkaline earth metals; Organic compounds (such as mono- or polycarboxylic acids) and salts thereof such as 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; Polymeric compounds such as ionic copolymers (ionomers).
    11. Fillers and reinforcing agents such as calcium carbonate, silicates, glass fibers, glass bulbs, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood powder and other natural products Or fibers, synthetic fibers.
    12. Triarylphosphines, such as triphenylphosphine.
    13. Other additives such as plasticizers, lubricants, emulsifiers, pigments, flow additives, catalysts, flow-controlling agents, optical brighteners, flame retardants, antistatic agents and blowing agents.
    Co-stabilizers are added at concentrations such as 0.01 to 10% by weight, based on the total amount of polycarbonate, polyester or polyketone or mixtures or combinations thereof to be stabilized.
    Particularly preferred additives are phenolic antioxidants (paragraph 1 above), hindered amines (paragraph 2.6 above), phosphite and phosphonite (paragraph 4 above), triarylphosphine (paragraph 12 above) and UV absorbers (2.1 above) Paragraphs 2.2 and 2.8).
    Component (b) and any other additives are incorporated into, or dissolved or dispersed in, a method known as component (a) [olycarbonate, polyester or polyketone or mixtures or combinations thereof], before or during molding. (b) is applied with component (a) followed by evaporation of the solvent. Component (b) may be added to the material to be stabilized (component (a)) in the form of a masterbatch containing the component at a concentration of 2.5 to 25% by weight.
    Component (b) may be added before or during the polymerization reaction or before the crosslinking reaction.
    Component (b) may be incorporated into component (a) to stabilize in pure or encapsulated form in wax, oil or polymer.
    Component (b) may be sprayed onto component (a) to be stabilized. By diluting other additives (such as the standard additives described above) or their melts, they may be sprayed onto component (a) to be stabilized with their additives. Application by spraying during the inactivation of the polymerization catalyst is particularly advantageous when the vapor used for inactivation is used for spraying.
    The polycarbonates, polyesters and polyketones or mixtures or combinations thereof stabilized in this manner are for example various, including glass, films, fibers, filaments, molding compositions, propyl or paint binders, in particular powder coatings, adhesives or putties. It can be used in the form. In a particularly preferred embodiment of the invention the polycarbonates, polyesters and polyketones or mixtures or combinations thereof stabilized in this way are used as glass substitutes such as for example windows, windshields, automotive glass or protective films.
    Component (b) is particularly suitable as a process stabilizer (heat stabilizer). It is preferred to add to component (a) before or during processing for this purpose.
    Thus, a preferred embodiment of the present invention is benzofuran- as a stabilizer of polycarbonates, polyesters or polyketones or mixtures or combinations thereof [component (a)] from decomposition by oxidation, heat and / or photoinduction. Use of compounds of the 2-one type.
    Component (b) is characterized by a change in color tone, for example, to minimize discoloration during processing of polycarbonates, polyesters and polyketones or mixtures or combinations thereof.
    The invention also provides for oxidation of polycarbonates, polyesters or polyketones or mixtures or combinations thereof comprising incorporating or applying one or more benzofuran-2-one type compounds [component (b)]. And stabilizing from decomposition by heat and / or photoinduction.
    Preferred compounds of the benzofuran-2-one type for use and stabilizing methods as stabilizers are the same as those described for compositions having polycarbonates, polyesters or polyketones or mixtures or combinations thereof.
    The invention is illustrated in more detail by the following examples, in which parts and percentages are by weight.
    Example 1 Stabilization of Polycarbonate
    A 1.0 kg dry polycarbonate powder and 0.1 to 0.6 g (0.01 to 0.06%) of the stabilizers listed in Table 1 were dried in a vacuum drying oven at 120 ° C. (Lexan R 115 of General Electric) for a Henschel mixer Mix for 2 minutes. This mixture was then extruded in a Schwabenthan extruder at up to 280 ° C. Thereafter, the polymerized yarn was granulated. Using an injection molding machine, a plate having a layer thickness of 2 mm was molded from the granules obtained at a maximum of 300 ° C. This plate was then aged in a circulating air oven at 135 ° C. for 2000 hours. Then, the yellow index (YI) of the plate was measured according to ASTM D 1925-70 and the transmittance was measured in% at 450 nm. A low YI value means less discoloration of the pattern, and a high YI value means severe discoloration. The less discoloration, the more effective the stabilizer. The higher the light transmittance value, the more effective the stabilizer is. The results are shown in Table 1 and Table 2.

    a) Comparative Example.
    b) Embodiments of the invention.
    c) Irgafos R 168 (Ciba Special Chemicals) is tris (2,4-di-tert-butylphenyl) phosphite.
    d) Compound (101) is a mixture of about 85 parts by weight of a compound of formula (5a) and about 15 parts by weight of a compound of formula (5b):
    e) Compound (102) is 3- [4- (2-acetoxyethoxy) phenyl] -5,7-di-tert-butyl-benzofuran-2-one of formula (5c):
    Example 2: Stabilization of Polycarbonate
    1.0 kg of polycarbonate powder dried for 8 hours in a vacuum drying oven at 120 ° C. (Lexan R 145 from General Electric) was charged with the stabilizers listed in Table (3) and mixed in a Henschel mixer for 2 minutes. This mixture was then extruded in a Swabbentan extruder at up to 280 ° C. Thereafter, this polymerized yarn was granulated. Using an injection molding machine, a plate having a layer thickness of 2 mm was molded from the granules obtained at a maximum of 300 ° C. This plate was then aged in a circulating air oven at 135 ° C. and time was measured until the yellow index (YI) reached 20 according to ASTM D 1925-70. The longer the time, the more effective the stabilizer is. The results are shown in Table (3).
    Footnotes a) to d) are described at the end of Table 2.
    f) Irganox R 1076 (Ciba Special Chemicals) is a compound of the formula:
    Example 3: Stabilization of Polycarbonate
    1.0 kg of dried polycarbonate powder for 8 hours in a vacuum drying oven at 120 ° C. (Lexan R 145 from General Electric) was charged with the stabilizers listed in the table below and mixed in a Henschel mixer for 2 minutes. This mixture was then extruded in a Swabbentan extruder at up to 280 ° C. Thereafter, this polymerized yarn was granulated. Using an injection molding machine, plates having layer thicknesses of 2, 4 and 8 mm were prepared from the granules obtained at up to 300 ° C. The yellowness index (YI) of the plate was measured according to ASTM D 1925-70. Low YI values indicate severe plate discoloration. The less discoloration, the more effective the stabilizer or stabilizer mixture. The results are shown in the table below.
    ExampleStabilizerYellow index of 2, 4 and 8 mm plates 2 mm4mm8 mm 3a a) -3.16.614.1 3b b) Compound (101) 0.006% d) Irgafos R 168 c) 0.022% Irgafos R 1076 f) 0.012%0.42.04.8
    Footnotes a) to f) are described at the ends of Tables 2 and 3.
    Example 4: Stabilization of Polybutylene Terephthalate (PBT)
    1.0 kg of polybutylene terephthalate powder dried for 10 hours in a vacuum drying oven at 100 ° C. (Crastin R S 600 from Ciba Specialty Chemical) was charged with the stabilizers listed in the table below and mixed in a Henschel mixer for 2 minutes. The mixture was then extruded in a twin screw extruder (Werstorp type) at 250 ° C. and then granulated. The granules obtained were molded in an injection molding machine at up to 260 ° C. to obtain small rods 4 × 6 mm thick and 50 mm long. This small rod was then aged in a circulating air oven at 160 ° C. After 360 hours, the impact strength of the rod was measured in KJ / m 2 units. The higher the value, the better the stabilization. The results are shown in the table below.
    Impact strength in oven-aging test at 160 ° C
    Footnotes a) to f) are described at the ends of Tables 2 and 3.
    g) Irganox R 245 (Ciba Specialty Chemicals) is a compound of the formula:
    Example 5: Stabilization of Polycarbonate
    1.0 kg of dry polycarbonate powder and stabilizers listed in the table below were charged in a vacuum drying oven at 120 ° C. (Lexan R 145 from General Electric) and mixed in a Henschel mixer for 2 minutes. This mixture was then extruded in a Swabbentan extruder at up to 280 ° C. Thereafter, the polymerized yarn was granulated. Using an injection molding machine, a plate having a layer thickness of 2 mm was molded from the granules obtained at a maximum of 300 ° C. The plates were then irradiated for 2500 hours in a weather resistance tester (WOM Cl 65) having an intensity of 0.35 W / m 2 at assay standard temperature 63 ° C., dry / wet cycle 102/18 minutes and 340 nm. The yellow index (YI) of the plate was then measured according to ASTM D 1925-70. A low YI value means less discoloration of the plate, and a high YI value means severe discoloration. The less discoloration, the more effective the stabilizer or stabilizer mixture. The results are shown in the table below:
    Footnotes a) to f) are described at the ends of Tables 2 and 3.
    h) Tinuvin R 234 (Ciba Specialty Chemicals) is a compound of the formula:
    i) Tinuvin R 360 (Ciba Specialty Chemicals) is a compound of the formula:
    j) Tinuvin R 1577 (Ciba Specialty Chemicals) is a compound of the formula:
    Example 6: Stabilization of Polycarbonate
    1.0 kg of dry polycarbonate powder and stabilizers listed in the table below were charged in a vacuum drying oven at 120 ° C. (Lexan R 145 from General Electric) and mixed for 2 minutes in a Henschel mixer. This mixture was then extruded in a Swabbentan extruder at up to 280 ° C. Thereafter, the polymerized yarn was granulated. The granules obtained were filled in a polystyrene box 1 cm thick and the yellowness index (YI) was measured according to ASTM D 1925-70. Low YI values indicate less discoloration of the sample, and high YI values indicate severe discoloration. The less discoloration, the more effective the stabilizer and stabilizer mixture. The results are shown in the table below:
    ExampleStabilizerYellow index 6a a) -10.1 6b a) GSY R P101 k) 0.05%5.0 6c b) GSY R P101 k) 0.04% Compound (101) d) 0.02%1.0
    Footnotes a, b and d are described at the end of Table 2.
    k) GSY R P101 (Yoshitomi) is a compound of the formula:
    Example 7: Stabilization of Polyester
    In a vacuum drying oven at 120 ° C. (Polyclear R T86 from Hoechst) 2.5 kg of dried polyester for 12 hours and the stabilizers listed in the table below were charged and mixed in a Henschel mixer for 2 hours. This mixture was then extruded in a Swabbentan extruder at up to 275 ° C. Thereafter, the polymerized yarn was granulated. The granules obtained were further dried in a vacuum drying oven for 12 hours. For the double measurement, 500 mg of the granules were heated to 290 ° C. over 10 minutes and stored for 1 hour under pure oxygen in 290 ° C. lancimate. The resulting gas separation product was continuously introduced into the recovered aqueous solution, and the conductivity (µS) of this solution was continuously measured. Low conductivity values mean that little separation product is produced, and high conductivity values mean that the separation product is significantly produced. The lower the conductivity value, the more effective the stabilizer is. The results are shown in the table below.
    ExampleStabilizerConductivity (μS) 7a a) -46 7b b) Compound (101) d) 0.20%33
    Footnotes a, b and d are described at the end of Table 2.
    Example 8: Stabilization of Polyester
    In a vacuum drying oven at 120 ° C. (Polyclear R T86 from Hoechst) 2.5 kg of dried polyester for 12 hours and the stabilizers listed in the table below were charged and mixed in a Henschel mixer for 2 hours. This mixture was then extruded in a Swabbentan extruder at up to 275 ° C. Thereafter, the polymerized yarn was granulated. The granules obtained were further dried in a vacuum drying oven for 12 hours. 15 mg of the granules were processed by a heating program in a thermograph (Mettler thermogravimetric analyzer) from a starting temperature of 30 ° C. When heated, the separation product was produced while reducing the weight of the original sample. The temperature when the weight loss of the sample reached 1% was measured. The higher the temperature when the weight loss reaches 1%, the better the stabilizer. The results are shown in the table below.
    ExampleStabilizerTemperature (℃) 8a a) -271 8b b) Compound (101) d) 0.20%277
    Footnotes a, b and d are described at the end of Table 2.
    Example 9: Stabilization of Polyester
    In a vacuum drying oven at 120 ° C. (Polyclear R T86 from Hoechst) 2.5 kg of dried polyester for 12 hours and the stabilizers listed in the table below were charged and mixed in a Henschel mixer for 2 hours. This mixture was then extruded in a Swabbentan extruder at up to 275 ° C. Thereafter, the polymerized yarn was granulated. The granules obtained were further dried in a vacuum drying oven for 12 hours. 15 mg of the granules were processed by a heating program in a thermograph (Mettler thermogravimetric analyzer) from a starting temperature of 30 ° C. When heated, the separation product was produced while reducing the weight of the original sample. It measured until it reached 290 degreeC, and also measured the weight loss of a sample. The lower the weight loss at 290 ° C., the more effective the stabilization. The results are shown in the table below.
    ExampleStabilizer% Weight loss at 290 ° C 9a a) -3.0 9b b) Compound (101) d) 0.20%2.5
    Footnotes a, b and d are described at the end of Table 2.
    Stabilizers according to the invention were effective in the polycarbonate, polyester sulfidation, impact strength, pyrolysis tests.
    权利要求:
    Claims (13)
    [1" claim-type="Currently amended] a) polycarbonates, polyesters or polyketones, or mixtures or combinations thereof, susceptible to degradation by oxidation, heat and / or light induction, and
    b) a composition comprising at least one compound of the benzofuran-2-one type.
    [2" claim-type="Currently amended] The composition of claim 1 wherein component (b) is a compound of formula (1):
    (One)
    Where
    If n is 1,
    R 1 is unsubstituted or C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 -alkylthio, hydroxy, halogen, amino, C 1 -C 4 alkylamino, phenylamino or di ( Naphthyl, phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-, substituted by C 1 -C 4 -alkyl) amino 1-naphthyl, thienyl, benzo [b] thienyl, naphtho [2,3-b] thienyl, thianthrenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxatiinyl, pyrrolyl, Imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolinyl, isoindoleyl, indolyl, indazolyl, furinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, Naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, putridinyl, carbazolyl, β-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, iso Thiazolyl, phenothiazinyl, isoxazolyl, furazanyl, biphenyl , Terphenyl, fluorenyl or phenoxazinyl, or R 1 is a radical of the formula (2):
    (2)
    if n is 2,
    R 1 is unsubstituted or C 1 -C 4 alkyl- or hydroxy-substituted phenylene or naphthylene; Or -R 12 -XR 13- ,
    R 2 , R 3 , R 4 and R 5 independently of one another are hydrogen, chloro, hydroxy, C 1 -C 25 -alkyl, C 7 -C 9 phenylalkyl, unsubstituted or C 1 -C 4 alkyl-substituted Phenyl; Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkyl; C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl) amino, C 1 -C 25 alkanoyloxy, C 1 -C 25 alkanoyl Amino, C 3 -C 25 alkenoyloxy; Oxygen, sulfur or in the middle of the chain C 3 -C 25 -alkanoyloxy comprising; C 6 -C 9 cycloalkylcarbonyloxy, benzoyloxy or C 1 -C 12 alkyl-substituted benzoyloxy; Or R 2 and R 3 , or R 3 and R 4 , or R 4 and R 5 combine with the linking carbon atom to form a benzene ring, or R 4 is additionally-(CH 2 ) p -COR 15 or-( CH 2 ) q OH, or if R 3 , R 5 and R 6 are hydrogen, R 4 is additionally a radical of the formula (3):
    (3)
    Where
    R 1 is as described above for n = 1,
    R 6 is hydrogen or a radical of formula (4):
    (4)
    Where
    R 4 is not a radical of formula (3) and R 1 is as described above for n = 1,
    R 7 , R 8 , R 9 , R 10 and R 11 independently of one another are hydrogen, halogen, hydroxy, C 1 -C 25 alkyl; Oxygen, sulfur or in the middle of the chain C 2 -C 25 alkyl comprising; C 1 -C 25 alkoxy; Oxygen, sulfur or in the middle of the chain C 2 -C 25 -alkoxy including; C 1 -C 25 alkylthio, C 3 -C 25 alkenyl, C 3 -C 25 -alkenyloxy, C 3 -C 25 alkynyl, C 3 -C 25 alkynyloxy, C 7 -C 9 phenylalkyl , C 7 -C 9 phenylalkoxy, unsubstituted or C 1 -C 4 alkyl-substituted phenyl; Unsubstituted or C 1 -C 4 alkyl-substituted phenoxy; Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkyl; Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkoxy; C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl) amino, C 1 -C 25 alkanoyl; Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkanoyl comprising; C 1 -C 25 alkanoyloxy; Oxygen, sulfur or in the middle of the chain C 3 -C 25 -alkanoyloxy comprising; C 1 -C 25 alkanoylamino, C 3 -C 25 alkenoyl; Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkenoyl comprising; C 3 -C 25 alkenoyloxy; Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkenoyloxy comprising; C 6 -C 9 cycloalkylcarbonyl, C 6 -C 9 cycloalkylcarbonyloxy, benzoyl or C 1 -C 12 alkyl-substituted benzoyl; Benzoyloxy or C 1 -C 12 -alkyl-substituted benzoyloxy; or Or in formula (2) R 7 and R 8 , or R 8 and R 11 , combine with the linking carbon atom to form a benzene ring,
    R 12 and R 13 are independently of each other unsubstituted or C 1 -C 4 alkyl-substituted phenylene or naphthylene,
    R 14 is hydrogen or C 1 -C 8 alkyl,
    R 15 is hydroxy, , C 1 -C 18 alkoxy or ,
    R 16 and R 17 are independently of each other hydrogen, CF 3 , C 1 -C 12 alkyl or phenyl, or R 16 and R 17 are unsubstituted in combination with a linking carbon atom or 1 to 3 C 1 -C 4 alkyl A C 5 -C 8 cycloalkylidene ring substituted by;
    R 18 and R 19 are independently of each other hydrogen, C 1 -C 4 alkyl or phenyl,
    R 20 is hydrogen or C 1 -C 4 alkyl,
    R 21 is hydrogen, unsubstituted or C 1 -C 4 alkyl-substituted phenyl; C 1 -C 25 alkyl; Oxygen, sulfur or in the middle of the chain C 2 -C 25 alkyl comprising; C 7 -C 9 phenylalkyl unsubstituted on phenyl or substituted by 1 to 3 C 1 -C 4 alkyl; Oxygen, sulfur or in the middle of the chain Or C 7 -C 25 phenylalkyl which is unsubstituted on the phenyl or substituted by 1 to 3 C 1 -C 4 alkyl, or R 20 and R 21 are unsubstituted in combination with a linking carbon atom or To form a C 5 -C 12 cycloalkylene ring substituted by 1 to 3 C 1 -C 4 alkyl;
    R 22 is hydrogen or C 1 -C 4 alkyl,
    R 23 is hydrogen, C 1 -C 25 alkanoyl, C 3 -C 25 alkenoyl; Oxygen, sulfur or in the middle of the chain C 3 -C 25 alkanoyl comprising; C 2 -C 25 alkanoyl substituted by di (C 1 -C 6 alkyl) phosphonate groups; C 6 -C 9 cycloalkylcarbonyl, tenoyl, furoyl, benzoyl or C 1 -C 12 alkyl-substituted benzoyl;

    or ,
    R 24 and R 25 are independently of each other hydrogen or C 1 -C 18 alkyl,
    R 26 is hydrogen or C 1 -C 8 alkyl,
    R 27 is a direct bond, C 1 -C 18 alkylene; Oxygen, sulfur or in the middle of the chain C 2 -C 18 alkylene comprising; C 2 -C 18 alkenylene, C 2 -C 20 alkylidene, C 7 -C 20 phenylalkylidene, C 5 -C 8 cycloalkylene, C 7 -C 8 bicycloalkylene, unsubstituted or C 1 -C 4 alkyl-substituted phenylene, or ego,
    R 28 is hydroxy, , C 1 -C 18 alkoxy or ,
    R 29 is oxygen, -NH- or ego,
    R 30 is C 1 -C 18 alkyl or phenyl,
    R 31 is hydrogen or C 1 -C 18 alkyl,
    M is a r-valent metal cation,
    X is a direct bond, oxygen, sulfur or -NR 31- ,
    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.
    [3" claim-type="Currently amended] The composition of claim 1 wherein component (b) is a compound of formula (5):
    (5)
    Where
    R 2 is hydrogen or C 1 -C 6 alkyl,
    R 3 is hydrogen,
    R 4 is hydrogen or C 1 -C 6 alkyl,
    R 5 is hydrogen,
    R 7 , R 8 , R 9 , R 10 and R 11 independently of one another are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or Provided that at least two R 7 , R 8 , R 9 , R 10 or R 11 are hydrogen;
    R 20 , R 21 and R 22 are hydrogen, and
    R 23 is C 2 -C 4 alkanoyl.
    [4" claim-type="Currently amended] The composition of claim 1 wherein component (b) is the following formula (5a) or (5b) or a mixture or combination of two compounds of formula (5a) and (5b):

    (5a) (5b)
    [5" claim-type="Currently amended] The composition of claim 1 wherein component (a) is a clear solid and a glassy molded article.
    [6" claim-type="Currently amended] 6. The composition of claim 5, wherein the molded article is transparent at wavelengths 350 to 700 nm.
    [7" claim-type="Currently amended] The composition of claim 1, wherein the polycarbonate component (a) is derived from bisphenol A.
    [8" claim-type="Currently amended] The composition of claim 1 wherein the polyester in component (a) is PEN, PTT, PET, PETG or PBT or copolymers or combinations thereof.
    [9" claim-type="Currently amended] The composition of claim 1 wherein component (b) is present in an amount of 0.0005 to 5% by weight, based on component (a).
    [10" claim-type="Currently amended] The composition of claim 1 comprising additionally other additives in addition to components (a) and (b).
    [11" claim-type="Currently amended] The composition of claim 10 comprising as another additive a phenolic antioxidant, a UV absorber, a light stabilizer or a process stabilizer.
    [12" claim-type="Currently amended] The composition of claim 10 comprising as an additional additive at least one organic phosphite or phosphonite type of compound.
    [13" claim-type="Currently amended] Polycarbonate, polyester or polyketone or mixtures or combinations thereof from decomposition by oxidation, heat and / or photoinduction, comprising incorporating or applying one or more benzofuran-2-one type compounds How to stabilize.
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    同族专利:
    公开号 | 公开日
    GB9804057D0|1998-04-22|
    JPH10306209A|1998-11-17|
    FR2760460A1|1998-09-11|
    GB2322861B|2001-04-18|
    NL1008496A1|1998-09-08|
    KR100530094B1|2006-03-09|
    BE1012881A5|2001-05-08|
    US6310220B1|2001-10-30|
    IT1298340B1|1999-12-20|
    GB2322861A|1998-09-09|
    DE19808938A1|1998-10-08|
    JP4217926B2|2009-02-04|
    ITMI980445A1|1998-09-07|
    ES2149678B1|2001-05-16|
    NL1008496C2|1998-11-13|
    FR2760460B1|2003-09-12|
    ES2149678A1|2000-11-01|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    1997-03-06|Priority to CH526/97
    1997-03-06|Priority to CH52697
    1998-03-06|Application filed by 피로스카 랍 보프, 시바 스페셜티 케미칼스 홀딩 인코포레이티드
    1998-11-25|Publication of KR19980079962A
    2006-03-09|Application granted
    2006-03-09|Publication of KR100530094B1
    优先权:
    申请号 | 申请日 | 专利标题
    CH526/97|1997-03-06|
    CH52697|1997-03-06|
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