Polycarbonate composition

Abstract

To provide polycarbonate resin compositions comprising stabilizers that more thoroughly protect polycarbonates from the deleterious effects of heat, light and oxygen.SOLUTION: The present invention provides polycarbonate compositions that comprise one or more additives selected from the group consisting of benzofuranone stabilizers of formula I, but are free of hindered phenolic antioxidants, where R1, R2, R3, R4, and R5 independently represent a hydrocarbon group with hydrogen, halogen, a hydroxy group or any substituent.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure is directed to polycarbonate compositions containing certain benzofuranone stabilizers. [Background technology]

[0002] Polycarbonate is a desirable thermoplastic polymer due to its strong mechanical properties and excellent optical properties, including high light transmittance, high gloss, and clarity. However, polycarbonate yellows and loses its optical and mechanical properties when exposed to periodic or constant high temperatures.

[0003] Polycarbonate is used in applications such as solar energy control window films for construction, automotive and commercial lamp covers, reflective housings for LED lighting, and light diffusing films for LED and LCD electronic display monitors. These applications are subject to high temperatures.

[0004] There is a need for more complete protection of polycarbonates from the deleterious effects of heat, light, and oxygen, which can result in yellowing, loss of transparency, and loss of gloss. Conventional hindered phenolic antioxidants and / or organic phosphite or phosphine stabilizers are generally used for polycarbonates.

[0005] Summary of the Invention A composition is disclosed comprising a polycarbonate and one or more additives selected from the group consisting of benzofuranone stabilizers of formula I: [ka] wherein R1, R2, R3, R4, and R5 are each independently hydrogen, halogen, hydroxy, C1-C 25 Alkyl, C2-C 25 Alkenyl, C2-C 25 Alkynyl, C7-C9 phenylalkyl, phenyl, C5-C8 cycloalkyl, C1-C 18Alkoxy, C1-C8 alkylamine, di(C1-C8 alkyl)amino, C1-C 25 Alkanoyloxy, C1-C 25 Alkanoylamino, C3-C 25 Alkenoyloxy or C3-C interrupted by 1 to 3 -O-, -S-, -NH-, or -N(C1-C8 alkyl)- 25 alkanoyloxy, wherein C1-C 25 Alkyl, C2-C 25 Alkenyl, C2-C 25 Alkynyl, C7-C9 phenylalkyl, phenyl, C5-C8 cycloalkyl, C1-C 18 Alkoxy, C1-C8 alkylamine, di(C1-C8 alkyl)amino, C1-C 25 Alkanoyloxy, C1-C 25 Alkanoylamino, C3-C 25 Alkenoyloxy, and interrupted C3-C 25 The alkenoyloxy is unsubstituted or substituted with 1 to 3 groups selected from halogen, hydroxy, thiol, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, and C1-C4 alkyl.

[0006] Also disclosed is a method for stabilizing polycarbonate against the deleterious effects of heat, light, and oxygen, the method comprising incorporating into the polycarbonate one or more additives selected from the group consisting of benzofuranone stabilizers of formula I:

[0007] Also disclosed are additive compositions comprising one or more benzofuranone stabilizers of Formula I and one or more organophosphorus stabilizers.

[0008] Detailed Disclosure Polycarbonates can be obtained by condensation from bisphenol A and phosgene or phosgene analogues, such as trichloromethyl chloroformate, triphosgene, or diphenyl carbonate, usually with the addition of a suitable transesterification catalyst, such as boron hydride, an amine such as 2-methylimidazole, or a quaternary ammonium salt. In addition to bisphenol A, other bisphenol components can also be used, and it is also possible to use monomers that are halogenated at the benzene nucleus. Suitable bisphenol components include, for example, 2,2-bis(4'-hydroxyphenyl)propane (bisphenol A), 2,4'-dihydroxydiphenylmethane, bis(2-hydroxyphenyl)methane, bis(4-hydroxyphenyl)methane, bis-(4-hydroxy-5-propylphenyl)methane, 1,1-bis(4'-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)cyclohexylmethane, 2,2-bis(4'-hydroxyphenyl)-1-phenylpropane, 2,2-bis(3',5'-dimethyl-4'-hydroxyphenyl)propane, 2,2-bis( Examples of suitable diols include 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, and 1,1-bis(4'-hydroxyphenyl)-3,3,5-trimethylcyclopentane. In addition to bisphenols, polycarbonates can be obtained from other diols, such as dianhydrohexitols, including isosorbide, isoidide, and isomannide. Polycarbonates can be made using one or more of the aforementioned diols, as well as additional diols. The polycarbonate may be branched with a suitable amount of difunctional or higher functional monomers.

[0009] In some embodiments, the polycarbonate may be present in the composition of the present disclosure in a majority amount, for example, from any one of about 55%, about 60%, about 65%, about 70%, about 75%, or about 80% by weight to any one of about 85%, about 90%, about 95%, about 96%, about 97%, about 98%, or about 99% by weight.

[0010] The polycarbonate may be in the form of a sheet, film, or molded part. The polycarbonate composition can be used, for example, as exterior materials for electrical and electronic products, automotive parts, building materials, optical components, etc.

[0011] In some embodiments, the polycarbonate compositions can be used in automotive headlamps, streetlights, solar energy control window films for construction (buildings), reflective housings for LED lighting, light diffusing films for LED and LCD electronic display monitors, backlight films for computer and large console display screens, and containers such as bottles. Automotive vehicles include cars, trucks, vans, construction vehicles, sport utility vehicles, motorcycles, and the like.

[0012] Polycarbonate products also include window glass, greenhouse glazing, roofing products, mirrors, goggles, sound-absorbing barriers, windshields (e.g., motorcycle windshields), solar cell covers or substrates, display covers, touch panels or screens, and parts for amusement machines (e.g., pinball machines).

[0013] The polycarbonate (PC) film may have a thickness of, for example, less than about 0.05 mm to about 0.50 mm, for example, from about 0.05 mm, 0.07 mm, 0.09 mm, 0.10 mm, 0.15 mm, about 0.20 mm, or about 0.25 mm to about 0.30 mm, about 0.35 mm, about 0.40 mm, about 0.45 mm, or about 0.50 mm.

[0014] Polycarbonate sheets may have thicknesses of, for example, about 0.5 mm to more than about 3.1 mm. PC sheets can be thicker, for example, in the case of bulletproof window sheets. PC sheets may be about 0.5 mm, about 0.7 mm, about 1.0 mm, about 1.5 mm, or about 2.0 mm to about 2.5 mm, about 2.7 mm, or about 3.1 mm or more.

[0015] Both films and sheets may be monolayer or multilayer and may include layers containing other polymers or plastics. Films and sheets may be prepared by extrusion or coextrusion processes.

[0016] In certain embodiments, the polycarbonate composition may be transparent to light having a wavelength of about 350 nm, about 360 nm, about 370 nm, about 380 nm, about 390 nm, about 400 nm, about 410 nm, about 420 nm, about 430 nm, about 440 nm, or any wavelength between about 450 nm and about 700 nm. In some embodiments, the polycarbonate composition is transparent to visible light (about 390 nm to about 700 nm). In some embodiments, transparent means that 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, or 99% of the light can pass through the composition.

[0017] Benzofuranones of the present invention include compounds of formula I: [ka] wherein R1, R2, R3, R4, and R5 are each independently hydrogen, halogen, hydroxy, C1-C 25 Alkyl, C2-C 25 Alkenyl, C2-C 25 Alkynyl, C7-C9 phenylalkyl, phenyl, C5-C8 cycloalkyl, C1-C 18 Alkoxy, C1-C8 alkylamine, di(C1-C8 alkyl)amino, C1-C 25 Alkanoyloxy, C1-C 25 Alkanoylamino, C3-C25 Alkenoyloxy or C3-C interrupted by 1 to 3 -O-, -S-, -NH-, or -N(C1-C8 alkyl)- 25 alkanoyloxy, wherein C1-C 25 Alkyl, C2-C 25 Alkenyl, C2-C 25 Alkynyl, C7-C9 phenylalkyl, phenyl, C5-C8 cycloalkyl, C1-C 18 Alkoxy, C1-C8 alkylamine, di(C1-C8 alkyl)amino, C1-C 25 Alkanoyloxy, C1-C 25 Alkanoylamino, C3-C 25 Alkenoyloxy, and interrupted C3-C 25 The alkenoyloxy is unsubstituted or substituted with 1 to 3 groups selected from halogen, hydroxy, thiol, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, and C1-C4 alkyl.

[0018] In certain embodiments, R1 and R2 are independently hydrogen or C1-C8 alkyl, and R3 and R4 are independently C1-C 12 alkyl, and R5 is C1-C7 alkyl, phenyl, C1-C8 alkylphenyl, 3,5-di(C1-C8 alkyl)-4-hydroxyphenyl, or C1-C8 alkyl(3,5-di(C1-C8 alkyl)-4-hydroxyphenyl).

[0019] In certain embodiments, R1 and R2 are hydrogen and R3 and R4 are C1-C8 alkyl. In some embodiments, R5 is C1-C4 alkyl, phenyl, C1-C4 alkylphenyl, 3,5-di(C1-C4 alkyl)-4-hydroxyphenyl, or C1-C4 alkyl(3,5-di(C1-C4 alkyl)-4-hydroxyphenyl).

[0020] Alkyl groups may be straight-chained or branched and include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-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, tert-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, and dodecyl.

[0021] Cycloalkyl includes cyclohexyl, cyclopentyl, and cycloheptyl. Halogen is fluoro, chloro, bromo, or iodo. Phenylalkyl includes benzyl and cumyl. Alkenyl and alkynyl are unsaturated versions of alkyl. For example, the alkyl portion of alkoxy can be defined the same way as for alkyl.

[0022] In certain embodiments, benzofuranones of the present disclosure include compounds of the following formula: [ka]

[0023] Benzofuranones of formula I can be prepared as described in US Pat. Nos. 6,881,774 and 8,840,810.

[0024] The polycarbonate composition may include one or more ultraviolet light absorbers (UVA). In some embodiments, the UV light absorber may be selected from the group consisting of hydroxyphenylbenzotriazoles, tris-aryl-s-triazines, hydroxybenzoates, 2-hydroxybenzophenones, and cyanoacrylate ultraviolet light absorbers.

[0025] Hydroxyphenylbenzotriazole UVAs are described, for example, in U.S. Pat. Nos. 3,004,896, 3,055,896, 3,072,585, 3,074,910, 3,189,615, 3,218,332, 3,230,194, 4,127,586, 4,226,763, 4,275,004, 4,278,589, 4,315,848, and 4,34 No. 7,180, No. 4,383,863, No. 4,675,352, No. 4,681,905, No. 4,853,471, No. 5,268,450, No. 5,278,314, No. 5,280,124 No. 5,319,091, No. 5,410,071, No. 5,436,349, No. 5,516,914, No. 5,554,760, No. 5,563,242, No. 5,574,166, No. 5 Nos. 6,607,987, 5,977,219, and 6,166,218, and include, for example, 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(3,5-di-t-butyl-2-hydroxyphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-t-butylphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-t-octylphenyl)-2H-benzotriazole, triazole, 5-chloro-2-(3,5-di-t-butyl-2-hydroxyphenyl)-2H-benzotriazole, 5-chloro-2-(3-t-butyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(3-sec-butyl-5-t-butyl-2-hydroxyphenyl)-2H-benzotriazole, 2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazole, 2-(3,5-di-t-amyl-2-hydroxyphenyl)-2H-benzotriazole, 2-(3,5-bis-α-cumyl-2-hydroxyphenyl)-2H-benzotriazole, 2-(3-t-butyl-2-hydroxy-5-(2-(ω-hydroxy-octa-(ethyleneoxy)carbonyl-ethyl)-,phenyl)-2H-benzotriazole, 2-(3-dodecyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(3-t-butyl-2-hydroxy-5-(2-octa-(ethyleneoxy)carbonyl-ethyl)-,phenyl)-2H-benzotriazole 2-(3-tert-butyl-5-(2-(2-ethylhexyloxy)carbonylethyl)-2-hydroxyphenyl)-5-chloro-2H-benzotriazole, 2-(3-tert-butyl-5-(2-(2-ethylhexyloxy)carbonylethyl)-2-hydroxyphenyl)-5-chloro-2H-benzotriazole, 2-(3-tert-butyl-5-(2-(2-ethylhexyloxy)carbonylethyl)-2-hydroxyphenyl)-5-chloro-2H-benzotriazole, 2-(3-tert-butyl-5-(2-(2-ethylhexyloxy)carbonylethyl)-2-hydroxyphenyl)-5-chloro-2H-benzotriazole, 2-(3-t-butyl-2-hydroxy-5-(2-methoxycarbonylethyl)phenyl)-5-chloro-2H-benzotriazole, 2-(3-t-butyl-2-hydroxy-5-(2-methoxycarbonylethyl)phenyl)-2H-benzotriazole, 2-(3-t-butyl-5-(2-(2-ethylhexyloxy)carbonylethyl)-2-hydroxyphenyl)-2H-benzotriazole, 2-(3-t-butyl-2-hydroxy-5-(2-isooctyloxycarbonylethyl)phenyl) -2H-benzotriazole, 2,2'-methylene-bis(4-t-octyl-(6-2H-benzotriazol-2-yl)phenol), 2-(2-hydroxy-3-α-cumyl-5-t-octylphenyl)-2H-benzotriazole, 2-(2-hydroxy-3-t-octyl-5-α-cumylphenyl)-2H-benzotriazole, 5-fluoro-2-(2-hydroxy-3,5-di-α-cumylphenyl)-2H-benzotriazole, 5-chloro-2-(2-hydroxy-3,5-Di-α-cumylphenyl)-2H-benzotriazole, 5-chloro-2-(2-hydroxy-3-α-cumyl-5-t-octylphenyl)-2H-benzotriazole, 2-(3-t-butyl-2-hydroxy-5-(2-isooctyloxycarbonylethyl)phenyl)-5-chloro-2H-benzotriazole, 5-trifluoromethyl-2-(2-hydroxy-3-α-cumyl-5-t-octylphenyl)-2H-benzotriazole, 5-trifluoromethyl-2-(2-hydroxy-5-t-octylphenyl)-2H-benzotriazole, 5-trifluoromethyl-2-(2-hydroxy-3,5-di-t-octylphenyl)-2H-benzotriazole, methyl 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-t-butyl These are methyl-4-hydroxyhydrocinnamate, 5-butylsulfonyl-2-(2-hydroxy-3-α-cumyl-5-t-octylphenyl)-2H-benzotriazole, 5-trifluoromethyl-2-(2-hydroxy-3-α-cumyl-5-t-butylphenyl)-2H-benzotriazole, 5-trifluoromethyl-2-(2-hydroxy-3,5-di-t-butylphenyl)-2H-benzotriazole, 5-trifluoromethyl-2-(2-hydroxy-3,5-di-α-cumylphenyl)-2H-benzotriazole, 5-butylsulfonyl-2-(2-hydroxy-3,5-di-t-butylphenyl)-2H-benzotriazole, and 5-phenylsulfonyl-2-(2-hydroxy-3,5-di-t-butylphenyl)-2H-benzotriazole.

[0026] Tris-aryl-s-triazine UVAs are described, for example, in U.S. Pat. Nos. 3,843,371, 4,619,956, 4,740,542, 5,096,489, 5,106,891, 5,298,067, 5,300,414, 5,354,794, 5,461,151, 5,476,937, 5,489,503, 5,543,518, 5,556,973, 5,597,854, and 5,681,9 55, 5,726,309, 5,736,597, 5,942,626, 5,959,008, 5,998,116, 6,013,704, 6,060,543, 6,242,598, and 6,255,483, such as 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-octyloxyphenyl)-s-triazine, CYASORB 1164, 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-octyloxyphenyl)-s-triazine, 2,4-bis[2-hydroxy-4-(2-hydroxyethoxy)phenyl]-6-(4-chlorophenyl)-s-triazine, 2,4-bis[2-hydroxy-4-(2-hydroxy-4-(2-hydroxyethoxy)phenyl]-6-(2,4-dimethylphenyl)-s-triazine, 2,4-bis[2-hydroxy-4-(2-hydroxy-4-(2-hydroxyethoxy)phenyl]-6-(2,4-dimethylphenyl)-s-triazine, 2,4-bis[2-hydroxy-4-(2-hydroxy-4-(2-hydroxyethoxy)phenyl]-6-(2,4-dimethylphenyl)-s-triazine, 2,4-bis[2-hydroxy-4-(2-acetoxyethoxy)phenyl]-6-(4-chlorophenyl)-s-triazine, 2,4-bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-s-triazine, 2,4-bis(4-biphenylyl)-6-(2-hydroxy-4-octyloxycarbonylethylideneoxyphenyl)-s-triazine, 2,4-Bis(4-biphenylyl)-6-(2-hydroxy-4-(2-ethylhexyl)oxyphenyl)-s-triazine, 2-phenyl-4-[2-hydroxy-4-(3-sec-butyloxy-2-hydroxypropyloxy)phenyl]-6-[2-hydroxy-4-(3-sec-amyloxy-2-hydroxypropyloxy)phenyl]-s-triazine, 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-benzyloxy-2-hydroxypropyloxy)phenyl]-s-triazine, 2,4-bis (2-hydroxy-4-n-butyloxyphenyl)-6-(2,4-di-n-butyloxyphenyl)-s-triazine, 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-nonyloxy*-2-hydroxypropyloxy)-5-α-cumylphenyl]-s-triazine (* indicates a mixture of octyloxy, nonyloxy, and decyloxy groups), methylenebis-{2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-butyloxy-2-hydroxypropoxy)phenyl]- s-triazine}, a mixture of methylene-bridged dimers bridged at the 3:5', 5:5', and 3:3' positions, in a ratio of 5:4:1, 2,4,6-tris(2-hydroxy-4-isooctyloxycarbonylisopropylideneoxyphenyl)-s-triazine, 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-hexyloxy-5-α-cumylphenyl)-s-triazine, 2-(2,4,6-trimethylphenyl)-4,6-bis[2-hydroxy-4-(3-butyloxy-2-hydroxypropyloxy)phenyl] -s-triazine, 2,4,6-tris[2-hydroxy-4-(3-sec-butyloxy-2-hydroxypropyloxy)phenyl]-s-triazine, a mixture of 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-(3-dodecyloxy-2-hydroxypropoxy)-phenyl)-s-triazine and 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-(3-tridecyloxy-2-hydroxypropoxy)-phenyl)-s-triazine, TINUVIN 400, 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-(3-(2-ethylhexyloxy)-2-hydroxypropoxy)-phenyl)-s-triazine, and 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine.

[0027] Hydroxybenzoate UV absorbers are, for example, esters of substituted and unsubstituted benzoic acid, such as 4-tert-butylphenyl salicylic acid, phenyl salicylic acid, octylphenyl salicylic acid, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.

[0028] 2-Hydroxybenzophenone UV absorbers are, for example, the 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy, and 2'-hydroxy-4,4'-dimethoxy derivatives.

[0029] Cyanoacrylate UV absorbers are, for example, pentaerythritol tetrakis(2-cyano-3,3-diphenylacrylate), α-cyano-β,β-diphenylacrylic acid ethyl ester or isooctyl ester, and α-cyano-β-methyl-p-methoxy-cinnamic acid methyl ester or butyl ester.

[0030] Many UVAs are commercially available, such as TINUVIN326, TINUVIN360, TINUVIN234, TINUVIN1577, TINUVIN1600, CYASORB UV1164, CYASORB THT, CYASORB UV2908, CHIMASSORB81, and UVINUL3030.

[0031] In some embodiments, the UV absorbers may be present in a total of about 0.01 weight percent (wt%), about 0.05 wt%, about 0.1 wt%, about 0.2 wt%, about 0.5 wt%, about 0.7 wt%, about 1.0 wt%, or about 1.2 wt%, to about 1.4 wt%, about 1.6 wt%, about 1.8 wt%, about 2.0 wt%, about 2.3 wt%, about 2.5 wt%, about 2.7 wt%, or about 3.0 wt%, based on the weight of the polycarbonate.

[0032] In certain embodiments, in a multilayer film or sheet, the inner bulk layer and the top or cap layer may comprise different UVAs.

[0033] The polycarbonate composition may optionally contain one or more organic phosphorus stabilizers, including organic phosphite and organic phosphonite stabilizers, such as triphenyl phosphite, diphenyl alkyl phosphite, phenyl dialkyl phosphite, tris(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite (F), tris(2,4-di-tert-butylphenyl) phosphite, bis(2,4-di-α-cumylphenyl)pentaerythritol diphosphite (K), diisodecyl pentaerythritol diphosphite (H), and bis(2,4-di-α-cumylphenyl)pentaerythritol diphosphite (K). Erythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite (D), bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite (E), bisisodecyloxy-pentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, tristearyl sorbitol triphosphate Phosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylene-diphosphonite (H), 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-dibenzo[d,f][1,3,2]dioxaphosphepine (C), 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g][1,3,2]dioxaphosphocin (A), bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl- 6-methylphenyl)ethyl phosphite (G), 2,2',2"-nitrilo[triethyltris(3,3'5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite] (B), bis(2,4-di-t-butylphenyl)octyl phosphite, poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenylsulfide-}octyl phosphite), poly(4,4'{-isopropylidenediphenol}-octyl phosphite), poly(4,4'-{isopropylidenediphenol}-octyl phosphite), poly(4,4'-{isopropylidenediphenol}-octyl phosphite),6-dibromophenol]}-octyl phosphite), poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenyl sulfide}-pentaerythrityl diphosphite), [ka] [ka] [ka] Includes:

[0034] In some embodiments, the organophosphorus stabilizer also includes an organophosphine stabilizer. The organophosphine stabilizer may be of the formula P(R1)(R2)(R3), where R1, R2, and R3 are each independently H, C1-C 20 alkyl, C3-C7 cycloalkyl, C2-C6 alkenyl, phenyl, or naphthyl, each of which is unsubstituted or has 1 to 3 of hydroxy, amino, acetoxy, C1-C4 alkoxy, C1-C 10 Alkyl, C1-C4 alkylcarbonyl, phenyl, or C 1- Substituted with C4 alkoxyphenyl.

[0035] In some embodiments, the organic phosphine stabilizer can be selected from triethylphosphine, triisopropylphosphine, tri-n-butylphosphine, tricyclohexylphosphine, allyldiphenylphosphine, triphenylphosphine, diphenylphosphine, tri-2,4-dimethylphenylphosphine, tri-2,4,6-trimethylphenylphosphine, tri-o-tolylphosphine, tri-o-anisylphosphine, diphenylbutylphosphine, diphenyl-octadecylphosphine, tris-(p-nonylphenyl)-phosphine, tris-naphthylphosphine, diphenyl-(hydroxymethyl)-phosphine, diphenyl-acetoxymethylphosphine, diphenyl-(beta-ethylcarboxyethyl)phosphine, diphenyl-benzylphosphine, diphenyl-(p-hydroxyphenyl)-phosphine, diphenyl-1,4-dihydroxyphenyl-2-phosphine, and phenyl-naphthyl-benzylphosphine.

[0036] The polycarbonate composition may optionally contain one or more hindered phenolic antioxidants, such as tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], and octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate.

[0037] In some embodiments, both an organophosphorus stabilizer and a hindered phenolic antioxidant may be present, such as tris(2,4-di-tert-butylphenyl)phosphite and pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], and / or octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate.

[0038] In some embodiments, the benzofuranones of the present disclosure are present in an amount of about 10 ppm by weight, about 25 ppm by weight, about 50 ppm by weight, about 100 ppm by weight, about 150 ppm by weight, about 175 ppm by weight, about 200 ppm by weight, about 225 ppm by weight, about 250 ppm by weight, about 275 ppm by weight, about 300 ppm by weight, about 325 ppm by weight, about 350 ppm by weight, about 400 ppm by weight, about 45 ppm by weight, about 50 ppm by weight, about 55 ppm by weight, about 60 ppm by weight, about 65 ppm by weight, about 66 ppm by weight, about 67 ppm by weight, about 68 ppm by weight, about 69 ppm by weight, about 70 ppm by weight, about 71 ppm by weight, about 72 ppm by weight, about 75 ppm by weight, about 76 ppm by weight, about 77 ppm by weight, about 78 ppm by weight, about 79 ppm by weight, about 80 ppm by weight, about 81 ppm by weight, about 82 ppm by weight, about 83 ppm by weight, about 84 ppm by weight, about 85 ppm by weight, about 86 ppm by weight, about 87 ppm by weight, about 88 ppm by weight, about 89 ppm by weight, about 90 ppm by weight, about 91 ppm by weight, about 92 ppm by weight, about 93 ppm by weight, about 94 ppm by weight, about 95 ppm by weight, about 96 ppm by weight, about 97 ppm by weight, about 98 ppm by weight, about 99 ppm by weight, about 99 ppm by weight, about 99 ppm by weight, about 99 ppm by weight, about 100 ppm by weight, about 100 ppm by weight, about 100 ppm by weight, about 100 ppm by weight, about 100 ppm by weight, about The polycarbonate is incorporated at a level of 0 ppm by weight, or any one of about 500 ppm by weight, to any one of about 550 ppm by weight, about 600 ppm by weight, about 650 ppm by weight, about 700 ppm by weight, about 750 ppm by weight, about 800 ppm by weight, about 850 ppm by weight, about 900 ppm by weight, about 950 ppm by weight, or about 1000 ppm by weight (0.1 weight percent (wt %)).

[0039] In other embodiments, the benzofuranones of the present disclosure are incorporated into the polycarbonate at a level of any one of about 0.1 wt%, about 0.5 wt%, about 0.75 wt%, about 1.0 wt%, about 1.5 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, about 3.5 wt%, or about 4.0 wt%, to any one of about 4.5 wt%, about 5.0 wt%, about 5.5 wt%, about 6.0 wt%, about 6.5 wt%, or about 7.0 wt% (weight percent), based on the weight of the polycarbonate.

[0040] Organophosphorus stabilizers, when present, are used at the weight levels outlined for the benzofuranones. In some embodiments, the one or more benzofuranones and the one or more organophosphorus compounds may be used in a weight / weight ratio of about 1 / 99, about 1 / 90, about 1 / 80, about 1 / 70, about 1 / 60, about 1 / 50, about 1 / 40, about 1 / 30, about 1 / 20, about 1 / 10, about 1 / 9, about 1 / 8, about 1 / 7, about 1 / 6, about 1 / 5, about 1 / 4, about 1 / 3, about 1 / 2, or about 1 / 1 to about 2 / 1, about 3 / 1, about 4 / 1, about 5 / 1, about 6 / 1, about 7 / 1, about 8 / 1, about 9 / 1, about 10 / 1, about 20 / 1, about 30 / 1, about 40 / 1, about 50 / 1, about 60 / 1, about 70 / 1, about 80 / 1, about 90 / 1, or about 99 / 1.

[0041] In some embodiments, the organophosphorus stabilizer, when present, is used at a weight level equal to or greater than that of the one or more benzofuranones. For example, in some embodiments, the weight / weight ratio of the one or more benzofuranones to the one or more organophosphorus stabilizers may be about 0.05, about 0.10, about 0.11, about 0.12, about 0.13, about 0.14, about 0.15, about 0.16, about 0.20, about 0.25, about 0.30, about 0.35, about 0.40, about 0.45, or about 0.50, to about 0.55, about 0.60, about 0.65, about 0.70, about 0.75, about 0.80, about 0.85, about 0.90, about 0.95, or about 1.0.

[0042] The weight / weight ratio of organophosphorus stabilizer to hindered phenolic antioxidant may be any one of about 9 / 1, about 8 / 1, about 7 / 1, about 6 / 1, about 5 / 1, about 4 / 1, 3 / 1, about 2 / 1, or about 1 / 1 to any one of about 1 / 2, about 1 / 3, about 1 / 4, about 1 / 5, about 1 / 6, about 1 / 7, about 1 / 8, or about 1 / 9.

[0043] In certain embodiments, the compositions of the present invention may be essentially free of organophosphorus stabilizers and / or phenolic antioxidants. The term "essentially free" means "not intentionally added," and may be present only in small amounts, for example, at levels of 100 ppm, 75 ppm, 50 ppm, 25 ppm, 15 ppm, 10 ppm, 5 ppm, or 2 ppm by weight based on the weight of the total composition.

[0044] The inventive benzofuranone and any additional additives can be incorporated into polycarbonate by known methods, for example, before or after molding, with or without subsequent evaporation of the solvent, or by applying a dissolved or dispersed additive mixture to the polycarbonate. The inventive benzofuranone and any additional additives can also be added to the polycarbonate in the form of a masterbatch, which contains, for example, about 2% to about 40% by weight of the additives, based on the total weight of the masterbatch. In the masterbatch form, the polymer of the masterbatch does not need to be the same as the polycarbonate. Molding can be carried out using known mixing equipment, such as a mixer, kneader, or extruder.

[0045] The benzofuranone of the present invention and any additional additives can be premixed or added separately. The benzofuranone of the present invention and any additional additives can also be added before or during polymerization or before crosslinking. The benzofuranone of the present invention and any additional additives can be incorporated into the polycarbonate in pure form or encapsulated in wax, oil, or polymer.

[0046] The benzofuranones of the present invention and any additional additives may also be sprayed onto polycarbonate. They may be diluted with other additives or their melts so that they may be sprayed onto polycarbonate along with these additives.

[0047] In certain embodiments, the benzofuranone additive of the present invention is incorporated into the polycarbonate by melt mixing in an extruder. The benzofuranone of the present invention and any additional additives may be added together or separately.

[0048] In some embodiments, additives may be incorporated into a polycarbonate film or sheet (substrate) via a coating process on the film / sheet. "Dip coating" involves continuously drawing the substrate through a liquid medium in which the additive(s) are adsorbed onto the surface or partially impregnated into the substrate. Such a coating process allows for higher concentrations of additives to be deposited on the substrate.

[0049] In some embodiments, the process for preparing polycarbonate compositions involves weighing raw materials, followed by dry blending of the raw materials. The blend may be fed into a screw extruder at a constant feed rate to extrude the material into the desired form, followed by water quenching and drying. The raw materials are mixed and introduced through a single feeder at the throat or feed zone of the extruder. Alternatively, some components may be introduced partway up the extruder barrel in the melting or mixing zone. For example, liquid raw materials may be introduced into later zones via liquid injection under pressure.

[0050] A typical flat film or cast extrusion line for film or sheet generally includes an extruder, a film or sheet die, a take-up and / or sheet cooling system, and a take-up or spooling system. For multilayer sheet or film structures, either a single die with multiple exits or multiple extruders can feed the molten polymer into a die appropriately designed for the multilayer construction. Optional post-processing of the extruded film before take-up can include stretch-draw devices to provide film orientation in the machine, transverse, or both directions to enhance certain mechanical film properties.

[0051] Below are some embodiments of the present disclosure. In a first embodiment, a composition is disclosed comprising a polycarbonate and one or more additives selected from the group consisting of benzofuranone stabilizers of formula I: [ka] wherein R1, R2, R3, R4, and R5 are each independently hydrogen, halogen, hydroxy, C1-C 25 Alkyl, C2-C 25 Alkenyl, C2-C 25 Alkynyl, C7-C9 phenylalkyl, phenyl, C5-C8 cycloalkyl, C1-C 18 Alkoxy, C1-C8 alkylamine, di(C1-C8 alkyl)amino, C1-C 25 Alkanoyloxy, C1-C 25 Alkanoylamino, C3-C 25 Alkenoyloxy or C3-C interrupted by 1 to 3 -O-, -S-, -NH-, or -N(C1-C8 alkyl)- 25 alkanoyloxy, wherein C1-C 25 Alkyl, C2-C 25 Alkenyl, C2-C 25 Alkynyl, C7-C9 phenylalkyl, phenyl, C5-C8 cycloalkyl, C1-C 18 Alkoxy, C1-C8 alkylamine, di(C1-C8 alkyl)amino, C1-C 25 Alkanoyloxy, C1-C 25 Alkanoylamino, C3-C 25 Alkenoyloxy, and interrupted C3-C 25 The alkenoyloxy is unsubstituted or substituted with 1 to 3 groups selected from halogen, hydroxy, thiol, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, and C1-C4 alkyl.

[0052] In a second embodiment, in the compound of formula I, R1 and R2 are independently hydrogen or C1-C8 alkyl, and R3 and R4 are independently C1-C 12and R5 is C1-C7 alkyl, phenyl, C1-C8 alkylphenyl, 3,5-di(C1-C8 alkyl)-4-hydroxyphenyl, or C1-C8 alkyl(3,5-di(C1-C8 alkyl)-4-hydroxyphenyl); or R1 and R2 are hydrogen and R3 and R4 are C1-C8 alkyl. In a third embodiment, a composition according to the first or second embodiment is disclosed, wherein R5 is C1-C4 alkyl, phenyl, C1-C4 alkylphenyl, 3,5-di(C1-C4 alkyl)-4-hydroxyphenyl, or C1-C4 alkyl(3,5-di(C1-C4 alkyl)-4-hydroxyphenyl). In a fourth embodiment, a composition according to any of the first to third embodiments is disclosed, wherein the benzofuranone stabilizer is selected from the group consisting of: [ka]

[0053] In a fifth embodiment, a composition according to any of the first to fourth embodiments is disclosed, which comprises, based on the weight of the polycarbonate, about 10 ppm by weight, about 25 ppm by weight, about 50 ppm by weight, about 100 ppm by weight, about 150 ppm by weight, about 175 ppm by weight, about 200 ppm by weight, about 225 ppm by weight, about 250 ppm by weight, about 275 ppm by weight, about 300 ppm by weight, about 325 ppm by weight, about 350 ppm by weight, about 400 ppm by weight, about 450 ppm by weight, about 500 ppm by weight, about 550 ppm by weight, about 560 ppm by weight, about 570 ppm by weight, about 580 ppm by weight, about 590 ppm by weight, about 600 ppm by weight, about 610 ppm by weight, about 620 ppm by weight, about 630 ppm by weight, about 640 ppm by weight, about 650 ppm by weight, about 660 ppm by weight, about 670 ppm by weight, about 680 ppm by weight, about 690 ppm by weight, about 700 ppm by weight, about 710 ppm by weight, about 720 ppm by weight, about 730 ppm by weight, about 740 ppm by weight, about 750 ppm by weight, about 760 ppm by weight, about 770 ppm by weight, about 780 ppm by weight, about 790 ppm by weight, about 800 ppm by weight, about 810 ppm by weight, about 820 ppm by weight, about 830 ppm by weight, about 840 ppm by weight, about 850 ppm by weight, about 860 ppm by weight, about 870 ppm by weight, about 880 ppm by weight, about 890 ppm by weight, about 900 ppm by weight, about 910 ppm by weight, about 920 The composition may comprise one or more benzofuranone stabilizers in an amount of from about 0.1 weight percent (wt %) to about 550 ppm, about 600 ppm, about 650 ppm, 700 ppm, about 750 ppm, about 800 ppm, about 850 ppm, about 900 ppm, about 950 ppm, or about 1000 ppm by weight.

[0054] In a sixth embodiment, a composition according to any of the first to fourth embodiments is disclosed, comprising any one of about 0.1 wt%, about 0.5 wt%, about 0.75 wt%, about 1.0 wt%, about 1.5 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, about 3.5 wt%, or about 4.0 wt%, to any one of about 4.5 wt%, about 5.0 wt%, about 5.5 wt%, about 6.0 wt%, about 6.5 wt%, or about 7.0 wt% (weight percent) of one or more benzofuranone stabilizers, based on the weight of the polycarbonate.

[0055] In a seventh embodiment, a composition according to any of the first to sixth embodiments is disclosed, which includes one or more organophosphorus stabilizers. In an eighth embodiment, a composition according to any of the first to seventh embodiments is disclosed, which includes one or more organophosphorus stabilizers selected from the group consisting of 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, bis(2,4-di-α-cumyl ... Diisodecylpentaerythritol diphosphite, diisodecylpentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, bisisodecyloxy-pentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol Diphosphite, tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)4,4'-biphenylene-diphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-dibenzo[d,f][1,3,2]dioxaphosphepine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g][1,3,2]dioxaphosphocin, bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, Bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 2,2',2"-nitrilo[triethyltris(3,3'5,5'-tetra-tert-butyl-1,1')-biphenyl-2,2'-diyl)phosphite], bis(2,4-di-t-butylphenyl)octyl phosphite, poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenylsulfide-}octyl phosphite), poly(4,4'{-isopropylidenediphenol}-octyl phosphite), poly(4,4'-{isopropylidenebis[2,6-dibromophenol]}-octyl phosphite), poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenyl sulfide}-pentaerythrityl diphosphite), [ka]

[0056] In a ninth embodiment, a composition according to any of the first to eighth embodiments is disclosed, which comprises about 10 ppm by weight, about 25 ppm by weight, about 50 ppm by weight, about 100 ppm by weight, about 150 ppm by weight, about 175 ppm by weight, about 200 ppm by weight, about 225 ppm by weight, about 250 ppm by weight, about 275 ppm by weight, about 300 ppm by weight, about 325 ppm by weight, about 350 ppm by weight, about 400 ppm by weight, based on the weight of the polycarbonate. about 450 ppm by weight, or about 500 ppm by weight to about 550 ppm by weight, about 600 ppm by weight, about 650 ppm by weight, about 700 ppm by weight, about 750 ppm by weight, about 800 ppm by weight, about 850 ppm by weight, about 900 ppm by weight, about 950 ppm by weight, or about 1000 ppm by weight (0.1 weight percent (wt %)) of one or more organophosphorus stabilizers.

[0057] In a tenth embodiment, a composition according to any of the first to ninth embodiments is disclosed, wherein the composition comprises one or more benzofuranone stabilizers and one or more organophosphorus stabilizers, wherein the weight / weight ratio of the benzofuranone stabilizer to the organophosphorus stabilizer is about 1 / 99, about 1 / 90, about 1 / 80, about 1 / 70, about 1 / 60, about 1 / 50, about 1 / 40, about 1 / 30, about 1 / 20, about 1 / 10, about 1 / 9, about 1 / 20, about 1 / 30, about 1 / 40, about 1 / 50, about 1 / 60, about 1 / 70, about 1 / 80, about 1 / 90, about 1 / 10 ... 1 / 8, about 1 / 7, about 1 / 6, about 1 / 5, about 1 / 4, about 1 / 3, about 1 / 2, or about 1 / 1 to about 2 / 1, about 3 / 1, about 4 / 1, about 5 / 1, about 6 / 1, about 7 / 1, about 8 / 1, about 9 / 1, about 10 / 1, about 20 / 1, about 30 / 1, about 40 / 1, about 50 / 1, about 60 / 1, about 70 / 1, about 80 / 1, about 90 / 1, or about 99 / 1.

[0058] In an eleventh embodiment, a composition according to any of the first to tenth embodiments is disclosed, wherein the composition comprises one or more benzofuranone stabilizers and one or more organophosphorus stabilizers, wherein the weight / weight ratio of the one or more benzofuranone stabilizers to the one or more organophosphorus stabilizers can be from any one of about 0.05, about 0.10, about 0.15, about 0.20, about 0.25, about 0.30, about 0.35, about 0.40, about 0.45, or about 0.50, to any one of about 0.55, about 0.60, about 0.65, about 0.70, about 0.75, about 0.80, about 0.85, about 0.90, about 0.95, or about 1.0.

[0059] In a twelfth embodiment, a composition according to any of embodiments 1-6 is disclosed, wherein the composition is essentially free of organophosphorus stabilizers. In a thirteenth embodiment, a composition according to any of embodiments 1-12 is disclosed, wherein the composition is essentially free of hindered phenolic antioxidants.

[0060] In a fourteenth embodiment, a composition according to any of the first to thirteenth embodiments is disclosed, wherein the composition is transparent to light having a wavelength from any of about 350 nm, about 360 nm, about 370 nm, about 380 nm, about 390 nm, about 400 nm, about 410 nm, about 420 nm, about 430 nm, about 440 nm, or about 450 nm to 700 nm.

[0061] In a fifteenth embodiment, a film, sheet, or molded article is disclosed that includes a composition according to any of embodiments 1 to 14. In a sixteenth embodiment, a film, sheet, or molded article according to the fifteenth embodiment is disclosed that is transparent to light having a wavelength of about 350 nm to about 700 nm.

[0062] In a seventeenth embodiment, a film, sheet, or molded article according to embodiment fifteen or sixteen is disclosed, wherein the film, sheet, or molded article is selected from the group consisting of an automobile headlamp cover, a street light cover, a solar energy control film, a reflective housing for a lighting fixture, and a light diffusing film.

[0063] In an eighteenth embodiment, a method of preparing a film, sheet, or molded article according to any of embodiments 15-17 is disclosed, the method comprising melt-mixing a composition.

[0064] In a nineteenth embodiment, a method for stabilizing polycarbonate against the deleterious effects of heat, light, and oxygen is disclosed, the method comprising incorporating into the polycarbonate one or more additives selected from the group consisting of benzofuranone stabilizers of formula I: [ka] wherein R1 and R2 are independently hydrogen or C1-C8 alkyl; R3 and R4 are independently C1-C 12 alkyl, and R5 is C1-C7 alkyl, phenyl, C1-C8 alkylphenyl, 3,5-di(C1-C8 alkyl)-4-hydroxyphenyl, or C1-C8 alkyl(3,5-di(C1-C8 alkyl)-4-hydroxyphenyl. In a twentieth embodiment, a method according to embodiment 19 is disclosed, wherein R1 and R2 are hydrogen, and R3 and R4 are C1-C8 alkyl. In a twenty-first embodiment, a method according to embodiment 19 or 20 is disclosed, wherein R5 is C1-C4 alkyl, phenyl, C1-C4 alkylphenyl, 3,5-di(C1-C4 alkyl)-4-hydroxyphenyl, or C1-C4 alkyl(3,5-di(C1-C4 alkyl)-4-hydroxyphenyl.

[0065] In a 22nd embodiment, a method according to any of embodiments 19-21 is disclosed, wherein the benzofuranone stabilizer is selected from the group consisting of: [ka]

[0066] In a 23rd embodiment, the method according to any of the 19-22 embodiments is disclosed, which comprises adding about 10 ppm by weight, about 25 ppm by weight, about 50 ppm by weight, about 100 ppm by weight, about 150 ppm by weight, about 175 ppm by weight, about 200 ppm by weight, about 225 ppm by weight, about 250 ppm by weight, about 275 ppm by weight, about 300 ppm by weight, about 325 ppm by weight, about 350 ppm by weight, about 400 ppm by weight, based on the weight of the polycarbonate. , about 450 ppm, or about 500 ppm by weight to about 550 ppm, about 600 ppm, about 650 ppm, about 700 ppm, about 750 ppm, about 800 ppm, about 850 ppm, about 900 ppm, about 950 ppm, or about 1000 ppm (0.1 weight percent (wt %)) of one or more benzofuranone stabilizers.

[0067] In a 24th embodiment, a method according to any of the 19-23 embodiments is disclosed, comprising incorporating any one of about 0.1 wt%, about 0.5 wt%, about 0.75 wt%, about 1.0 wt%, about 1.5 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, about 3.5 wt%, or about 4.0 wt%, to any one of about 4.5 wt%, about 5.0 wt%, about 5.5 wt%, about 6.0 wt%, about 6.5 wt%, or about 7.0 wt% (weight percent) of one or more benzofuranone stabilizers, based on the weight of the polycarbonate.

[0068] In a twenty-fifth embodiment, a method according to any of embodiments 19-24 is disclosed, comprising incorporating one or more organophosphorus stabilizers. In a twenty-sixth embodiment, a method according to any of embodiments 19-25 is disclosed, comprising incorporating one or more organophosphorus stabilizers selected from the group consisting of 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, bis(2,4 -di-α-cumylphenyl)pentaerythritol diphosphite, diisodecylpentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, bisisodecyloxy-pentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri- tert-butylphenyl)pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)4,4'-biphenylene-diphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-dibenzo[d,f][1,3,2]dioxaphosphepine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g][1,3,2]dioxaphosphocin, bis(2,4-di -tert-butyl-6-methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 2,2',2"-nitrilo[triethyltris(3,3'5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite], bis(2,4-di-t-butylphenyl)octyl phosphite, poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenylsulfide-}octyl phosphite), poly(4,4'{-isopropylidenediphenol}-octyl phosphite), poly(4,4'-{isopropylidenebis[2,6-dibromophenol]}-octyl phosphite), poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenyl sulfide}-pentaerythrityl diphosphite), [ka]

[0069] In a 27th embodiment, the method according to any of the 19-26 embodiments is disclosed, wherein the polycarbonate is a polycarbonate having a polyisoprene content of about 10 ppm by weight, about 25 ppm by weight, about 50 ppm by weight, about 100 ppm by weight, about 150 ppm by weight, about 175 ppm by weight, about 200 ppm by weight, about 225 ppm by weight, about 250 ppm by weight, about 275 ppm by weight, about 300 ppm by weight, about 325 ppm by weight, about 350 ppm by weight, about 400 ppm by weight, based on the weight of the polycarbonate. pm, about 450 ppm, or about 500 ppm by weight to about 550 ppm, about 600 ppm, about 650 ppm, about 700 ppm, about 750 ppm, about 800 ppm, about 850 ppm, about 900 ppm, about 950 ppm, or about 1000 ppm by weight (0.1 weight percent (wt %)) of one or more organophosphorus stabilizers.

[0070] In a twenty-eighth embodiment, a method according to any of embodiments 19-27 is disclosed, comprising incorporating one or more benzofuranone stabilizers and one or more organophosphorus stabilizers, wherein the weight / weight ratio of benzofuranone stabilizers to organophosphorus stabilizers is about 1 / 99, about 1 / 90, about 1 / 80, about 1 / 70, about 1 / 60, about 1 / 50, about 1 / 40, about 1 / 30, about 1 / 20, about 1 / 10, about 1 / 9 , about 1 / 8, about 1 / 7, about 1 / 6, about 1 / 5, about 1 / 4, about 1 / 3, about 1 / 2, or about 1 / 1, to about 2 / 1, about 3 / 1, about 4 / 1, about 5 / 1, about 6 / 1, about 7 / 1, about 8 / 1, about 9 / 1, about 10 / 1, about 20 / 1, about 30 / 1, about 40 / 1, about 50 / 1, about 60 / 1, about 70 / 1, about 80 / 1, about 90 / 1, or about 99 / 1.

[0071] In a twenty-ninth embodiment, a method according to any of the nineteenth to twenty-eighth embodiments is disclosed, comprising incorporating one or more benzofuranone stabilizers and one or more organophosphorus stabilizers, wherein the weight / weight ratio of the one or more benzofuranone stabilizers to the one or more organophosphorus stabilizers can be from any one of about 0.05, about 0.10, about 0.15, about 0.20, about 0.25, about 0.30, about 0.35, about 0.40, about 0.45, or about 0.50, to any one of about 0.55, about 0.60, about 0.65, about 0.70, about 0.75, about 0.80, about 0.85, about 0.90, about 0.95, or about 1.0.

[0072] In a 30th embodiment, a method according to any of embodiments 19-24 is disclosed, wherein the method does not include incorporating an organophosphorus stabilizer. In a 31st embodiment, a method according to any of embodiments 19-30 is disclosed, wherein the method does not include incorporating a hindered phenolic antioxidant.

[0073] In a thirty-second embodiment, an additive composition is disclosed comprising one or more benzofuranone stabilizers of formula I: [ka] wherein R1 and R2 are independently hydrogen or C1-C8 alkyl; R3 and R4 are independently C1-C 12 alkyl, and R5 is C1-C7 alkyl, phenyl, C1-C8 alkylphenyl, 3,5-di(C1-C8 alkyl)-4-hydroxyphenyl, or C1-C8 alkyl(3,5-di(C1-C8 alkyl)-4-hydroxyphenyl), and one or more organophosphorus stabilizers.

[0074] In a thirty-third embodiment, a composition according to the thirty-second embodiment is disclosed, wherein R1 and R2 are hydrogen, and R3 and R4 are C1-C8 alkyl. In a thirty-fourth embodiment, a composition according to embodiment 32 or 33 is disclosed, wherein R5 is C1-C4 alkyl, phenyl, C1-C4 alkylphenyl, 3,5-di(C1-C4 alkyl)-4-hydroxyphenyl, or C1-C4 alkyl(3,5-di(C1-C4 alkyl)-4-hydroxyphenyl.

[0075] In a thirty-fifth embodiment, a composition according to any of embodiments 33-34 is disclosed, wherein the benzofuranone stabilizer is selected from the group consisting of: [ka]

[0076] In a thirty-sixth embodiment, a composition according to any of the thirty-second to thirty-five embodiments is disclosed, comprising one or more organophosphorus stabilizers selected from the group consisting of 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, bis(2,4-di-α-cumylphenyl)pentaerythritol diphosphite, Sulfite, diisodecylpentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, bisisodecyloxy-pentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, tristearyl sorbitol triphosphate Phosphite, tetrakis(2,4-di-tert-butylphenyl)4,4'-biphenylene-diphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-dibenzo[d,f][1,3,2]dioxaphosphepine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g][1,3,2]dioxaphosphocin, bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite , 2,2',2"-nitrilo[triethyltris(3,3'5,5'-tetra-tert-butyl-1,1')-biphenyl-2,2'-diyl)phosphite], bis(2,4-di-t-butylphenyl)octyl phosphite, poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenyl sulfide-}octyl phosphite), poly(4,4'{-isopropylidenediphenol}-octyl phosphite), poly(4,4'-{isopropylidenebis[2,6-dibromophenol]}-octyl phosphite), poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenyl sulfide}-pentaerythrityl diphosphite), [ka]

[0077] In a thirty-seventh embodiment, a composition according to any of embodiments 32-36 is disclosed, wherein the weight / weight ratio of benzofuranone stabilizer to organophosphorus stabilizer is about 1 / 99, about 1 / 90, about 1 / 80, about 1 / 70, about 1 / 60, about 1 / 50, about 1 / 40, about 1 / 30, about 1 / 20, about 1 / 10, about 1 / 9, about 1 / 8, about 1 / 7, about 1 / 6, about 1 / 5, about The ratio is from any one of 1 / 4, about 1 / 3, about 1 / 2, or about 1 / 1 to any one of about 2 / 1, about 3 / 1, about 4 / 1, about 5 / 1, about 6 / 1, about 7 / 1, about 8 / 1, about 9 / 1, about 10 / 1, about 20 / 1, about 30 / 1, about 40 / 1, about 50 / 1, about 60 / 1, about 70 / 1, about 80 / 1, about 90 / 1, or about 99 / 1.

[0078] In a thirty-eighth embodiment, a composition according to any of the thirty-second to thirty-sixth embodiments is disclosed, wherein the weight / weight ratio of the one or more benzofuranone stabilizers to the one or more organophosphorus stabilizers can be from any one of about 0.05, about 0.10, about 0.15, about 0.20, about 0.25, about 0.30, about 0.35, about 0.40, about 0.45, or about 0.50, to any one of about 0.55, about 0.60, about 0.65, about 0.70, about 0.75, about 0.80, about 0.85, about 0.90, about 0.95, or about 1.0.

[0079] In a thirty-ninth embodiment, a composition according to any of embodiments 32-38 is disclosed, wherein the composition is essentially free of hindered phenolic antioxidants.

[0080] The articles "a" and "an" herein refer to one or to more than one (e.g., at least one) of the grammatical object. All ranges cited herein are inclusive. The term "about" is used throughout to express and account for small variations. For example, "about" means that a numerical value may vary by ±5%, ±4%, ±3%, ±2%, ±1%, ±0.5%, ±0.4%, ±0.3%, ±0.2%, ±0.1%, or ±0.05%. All numerical values, whether explicitly stated or not, are modified by the term "about." Numerical values ​​modified by the term "about" include the specific identified value. For example, "about 5.0" includes 5.0.

[0081] All U.S. patents, U.S. patent applications, and published U.S. patent applications discussed herein are hereby incorporated by reference.

[0082] Unless otherwise specified, all parts and percentages are by weight. Weight percent (wt %) is based on the total composition, excluding any volatile materials, unless otherwise specified. [Example]

[0083] The polycarbonate used in the examples was LEXAN 141, which is determined to contain from about 600 ppm to about 650 ppm tris(2,4-di-t-butylphenyl) phosphite and from about 250 ppm to about 300 ppm tris(2,4-di-t-butylphenyl) phosphate. The additives used in the following examples were: Phosphite: tris(2,4-di-t-butylphenyl)phosphite; Hindered phenol: octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate; Triazine A: 2,4-bis(4-biphenylyl)-6-(2-hydroxy-4-(2-ethylhexyl)oxyphenyl)-s-triazine; Triazine B: 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine; Benzotriazole A: 2-(2-hydroxy-5-t-octylphenyl)-2H-benzotriazole; Benzotriazole B: 2,2'-methylene-bis(4-t-octyl-(6-2H-benzotriazol-2-yl)phenol); TPP: triphenylphosphine; [ka]

[0084] Compound C is disclosed, for example, in US Pat. No. 7,390,912, where n=4.

[0085] Example 1 Oven Aging The additives are dry mixed with the polycarbonate to provide the following formulation: Additive levels are reported in ppm (parts per million) by weight, based on the weight of the polycarbonate. [Table 1]

[0086] The mixed polycarbonate formulations are injection molded into 2 x 2 x 0.125 inch plaques. The plaques are subjected to oven aging at 125°C and monitored for up to 12,000 hours. Haze is determined as an average of three plaques. The Yellowness Index (YI), Delta E (ΔE), Transmittance (T), and Haze determined after 12,000 hours of oven aging at 125°C for plaques containing Samples 1-9 are reported below. [Table 2]

[0087] Example 2 Oven Aging The additives are dry mixed with the polycarbonate to provide the following formulation: Additive levels are reported in ppm by weight, based on the weight of the polycarbonate. [Table 3]

[0088] The mixed polycarbonate formulations are injection molded into 2 x 2 x 0.125 inch plaques. The plaques are oven aged at 125°C. The Yellowness Index (YI) is determined at zero and 5055 hours. [Table 4]

[0089] Example 3 Accelerated Photoaging The additives are dry mixed with the polycarbonate to provide the following formulation: Additive levels are in ppm by weight based on the weight of the polycarbonate. [Table 5]

[0090] The mixed polycarbonate formulations are injection molded into 2 x 2 x 0.125 inch plaques. The plaques are subjected to accelerated weathering in a xenon-arc Weather-O-Meter. The yellowness index (YI) is determined at time zero and 3022 hours. Delta YI (ΔYI) is the YI at 3022 hours minus the YI at time zero. The results are as follows: [Table 6]

Claims

1. 1. A composition comprising a polycarbonate and a benzofuranone stabilizer of the formula: wherein the composition comprises 10 ppm to 1000 ppm by weight of the benzofuranone stabilizer based on the weight of the polycarbonate. 【Chemistry 1】

2. The composition of claim 1 further comprising one or more organophosphorus stabilizers.

3. 3. The composition of claim 2, wherein the one or more organophosphorus stabilizers are selected from the group consisting of organophosphite stabilizers, organophosphonite stabilizers, and organophosphine stabilizers.

4. The one or more organophosphorus stabilizers may be selected from the group consisting of 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, bis(2,4-di-α-cumylphenyl)pentaerythritol diphosphite, diisodecyl pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, Erythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, bisisodecyloxy-pentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)4,4'-biphenylene-diphosphonite, 6-isodecyloxy-pentaerythritol diphosphite, Sooctyloxy-2,4,8,10-tetra-tert-butyl-dibenzo[d,f][1,3,2]dioxaphosphepine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g][1,3,2]dioxaphosphocin, bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 2,2',2"-nitrilo[triethyltris(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl] bis(2,4-di-t-butylphenyl)octyl phosphite, poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenyl sulfide}octyl phosphite), poly(4,4'{-isopropylidenediphenol}-octyl phosphite), poly(4,4'-{isopropylidenebis[2,6-dibromophenol]}-octyl phosphite), poly(4,4'-{2,2'-dimethyl-5,5'-di-t-butylphenyl sulfide}-pentaerythrityl diphosphite), 【Chemistry 2】 3. The composition of claim 2, wherein the aryl phenyl phosphine is selected from the group consisting of triethylphosphine, triisopropylphosphine, tri-n-butylphosphine, tricyclohexylphosphine, allyldiphenylphosphine, triphenylphosphine, diphenylphosphine, tri-2,4-dimethylphenylphosphine, tri-2,4,6-trimethylphenylphosphine, tri-o-tolylphosphine, tri-o-anisylphosphine, diphenylbutylphosphine, diphenyl-octadecylphosphine, tris-(p-nonylphenyl)-phosphine, tris-naphthylphosphine, diphenyl-(hydroxymethyl)-phosphine, diphenyl-acetoxymethylphosphine, diphenyl-(beta-ethylcarboxyethyl)phosphine, diphenyl-benzylphosphine, diphenyl-(p-hydroxyphenyl)-phosphine, diphenyl-1,4-dihydroxyphenyl-2-phosphine, and phenyl-naphthyl-benzylphosphine.

5. 10. The composition of claim 1, further comprising 10 ppm to 1000 ppm by weight, based on the weight of the polycarbonate, of one or more organophosphorus stabilizers.

6. 10. The composition of claim 1, further comprising 200 ppm to 800 ppm by weight, based on the weight of the polycarbonate, of one or more organic phosphite stabilizers.

7. 10. The composition of claim 1 further comprising 200 ppm to 800 ppm by weight, based on the weight of the polycarbonate, of one or more organophosphine stabilizers.

8. 10. The composition of claim 1, wherein the composition comprises one or more organophosphorus stabilizers, and wherein the weight / weight ratio of the benzofuranone stabilizer to the one or more organophosphorus stabilizers is from 0.05 to 1.

0.

9. The composition of claim 1 , wherein the composition comprises one or more ultraviolet absorbers.

10. 10. The composition of claim 1 further comprising 0.2 to 1.6 weight percent of a tris-aryl-s-triazine UV absorber, based on the weight of the polycarbonate.

11. 10. The composition of claim 1 further comprising 0.2% to 1.6% by weight, based on the weight of the polycarbonate, of a hydroxyphenylbenzotriazole UV absorber.

12. 10. The composition of claim 1, wherein the composition is essentially free of hindered phenolic antioxidants.

13. 10. The composition of claim 1, wherein when injection molded at 125°C to form a plaque, the plaque has a yellowness index of 15.9 to 21.

2.

14. The composition of claim 2, wherein the one or more organophosphorus stabilizers comprise tris(2,4-di-tert-butylphenyl) phosphite.

15. 10. The composition of claim 1, wherein when injection molded at 125°C to form a plaque, the plaque has a transmittance (T) of 81.9 to 83.

4.

16. 10. The composition of claim 1, wherein when injection molded at 125°C to form a plaque, the plaque has a haze of 8.7 to 11.

3.

17. 10. An article selected from a film, sheet, or molded article comprising the composition of claim 1.

18. 18. The article of claim 17, which is transparent to light having a wavelength of 400 nm to 700 nm.

19. 18. The article of claim 17, selected from the group consisting of an automobile headlamp cover, a street light cover, a solar energy control film, a reflective housing for a lighting fixture, and a light diffusing film.

20. 20. A method of preparing the article of claim 17, comprising melt-mixing the composition.

21. 10. A method for stabilizing polycarbonate against the deleterious effects of heat, light, and oxygen, comprising incorporating the benzofuranone stabilizer of claim 1 into polycarbonate.

22. The benzofuranone stabilizer of claim 1; and one or more organophosphorus stabilizers.

23. 23. The composition of claim 22, wherein the weight / weight ratio of the benzofuranone stabilizer to the one or more organophosphorus stabilizers is from 0.05 to 1.

0.

24. 23. The composition of claim 22, wherein the composition is essentially free of hindered phenolic antioxidants.

25. 23. The composition of claim 22, wherein the composition further comprises one or more ultraviolet absorbers.

26. 23. The composition of claim 22, further comprising 2,4-bis(4-biphenylyl)-6-(2-hydroxy-4-(2-ethylhexyl)oxyphenyl)-s-triazine, 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine, 2-(2-hydroxy-5-t-octylphenyl)-2H-benzotriazole, 2,2'-methylene-bis(4-t-octyl-(6-2H-benzotriazol-2-yl)phenol), triphenylphosphine, or a combination thereof.

Images