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A Stabilizer Mixture

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A Stabilizer Mixture (19) TZZ _ _T (11) EP 2 876 126 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 27.05.2015 Bulletin 2015/22 C08G 64/02 (2006.01) C08K 5/3475 (2006.01) C08L 69/00 (2006.01) (21) Application number: 13194284.9 (22) Date of filing: 25.11.2013 (84) Designated Contracting States: (72) Inventors: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB • Bruchmann, Bernd GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO 67251 Freinsheim (DE) PL PT RO RS SE SI SK SM TR • Tartarini, Cinzia Designated Extension States: 4051 Basel (CH) BA ME • Schrinner, Kerstin 4056 Basel (CH) (71) Applicant: BASF SE 67056 Ludwigshafen (DE) (54) A stabilizer mixture (57) A stabilizer mixture, which is liquid at a temperature of 10 to 40°C and a pressure of 500 to 1500 mbar, containing components (I) and (II), wherein component (I) is for example 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methylphenol, or 3-[3-(2H-benzotriazo-2-yl)-5-t-butyl-4-hydroxybenzyl]propanoic acid C7-C9alkyl ester and component (II) is a hyperbranched polycarbonate obtainable by the reaction of (a) a compound of the formula (IIa) R0(-O-A0-OH)3 (IIa) wherein Ro is a C3-C20alkanetriyl and Ao is C1-C10alkylene; (b) a compound of the formula (IIb) wherein X1 and X2 independently of one another are an electron withdrawing functional group; and (c) a compound of the formula (IIc) wherein R1 is hydrogen, oxygen, C1-C20alkyl, C1-C20alkyloxy, C3-C12cycloalkyl, C3-C12cycloalkyloxy, C2-C20acyl or C7-C12aryloxycarbonyl; A1 is a direct bond or C 1-C10alkylene; X3 is -OH, -SH, -NH 2, -NH(C1-C4alkyl), isocyanate, epoxy, -COOH, -COOR2, or -C(O)Cl; and R2 is C1-C4alkyl or C6-C10aryl. EP 2 876 126 A1 Printed by Jouve, 75001 PARIS (FR) EP 2 876 126 A1 Description [0001] The present invention relates to a stabilizer mixture, an organic material, preferably a thermoplastic poly- urethane, stabilized with said stabilizer mixture against degradation induced by light, heat or oxidation and the corre- 5 sponding use of said stabilizer mixture. [0002] The present invention relates in particular to a stabilizer mixture, which is liquid at a temperature of 10° to 40°C and a pressure of 500 to 1500 mbar, preferably 15° to 30°C and 800-1200 mbar, in particular 25°C and 1000 mbar, containing components (I) and (II), wherein component (I) is 10 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methylphenol, 3-[3-(2H-benzotriazo-2-yl)-5-t-butyl-4-hydroxybenzyl]propanoic acid C7-C9alkyl ester, or a mixture comprising the compounds of the formulae (Ia), (Ib) and (Ic), preferably 40 to 60 %, in particular 52%, by weight of the compound of the formula (Ia), 30 to 40 %, in particular 35%, by weight of the compound of the formula (Ib) 15 and 10 to 15 %, in particular 13%, by weight of the compound of the formula (Ic); the sum of the compounds being present in said mixture of component (I) being 100% by weight, 20 25 30 35 wherein n is a number from 1 to 10, and component (II) is a hyperbranched polycarbonate obtainable by the reaction of (a) a compound of the formula (IIa), for example in a concentration of 10-59 mol-%, preferably 10-55 mol-% and in 40 particular 10-49 mol-%, R0(-O-A0-OH)3 (IIa) wherein Ro is a C3-C20alkanetriyl and Ao is C1-C10alkylene; 45 (b) a compound of the formula (IIb), for example in a concentration of 40-60 mol-%, preferably 45-55 mol-% and in particular 50 mol-%, 50 wherein X1 and X2 independently of one another are an electron withdrawing functional group; 55 and (c) a compound of the formula (IIc), for example in a concentration of 1-50 mol-%, preferably 1-45 mol-% and in particular 1-40 mol-%, 2 EP 2 876 126 A1 5 wherein R1 is hydrogen, oxygen, C1-C20alkyl, C1-C20alkyloxy, C3-C12cycloalkyl, C3-C12cycloalkyloxy, C2-C20acyl 10 or C7-C12aryloxycarbonyl; A1 is a direct bond or C 1-C10alkylene; X3 is -OH, -SH, -NH2, -NH(C1-C4alkyl), isocyanate, epoxy, -COOH, -COOR2, or -C(O)Cl; and R2 is C1-C4alkyl or C6-C10aryl. 15 [0003] The weight ratio of components (I) to (II) is for example 1:20 to 20:1, preferably 1:10 to 10:1, in particular 1:5 to 5:1. [0004] An example of C5-C20alkanetriyl is the group (H5C2)C(CH2-)3. [0005] Preferred examples of C1-C10alkylene are methylene, ethylene, propylene and butylene. [0006] Examples of an electron withdrawing functional group are halogen, C 1-C10alkoxy,C 6-C10aryloxy or -O-C(O)-hal- ogen, in particular chlorine, methoxy, ethoxy, propoxy, butoxy, phenyloxy and -OC(O)-Cl. 20 [0007] Examples of alkyl having up to 20 carbon atoms are 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, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetra-meth- ylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl and eicosyl. 25 [0008] Examples of alkoxy having up to 20 carbon atoms are methoxy, ethoxy, propoxy, iso-propoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, dodecyloxy, tetradecyloxy, hexadecyloxy and octadecyloxy. [0009] Examples of C 3-C12cycloalkyl are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl and cyclododecyl. C5-C8Cycloalkyl, in particular cyclopentyl and cyclohexyl, is preferred. [0010] Examples of C 3-C12cycloalkyloxy are cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, cyclodecy- 30 loxy and cyclododecyloxy. C5-C8Cycloalkyloxy, in particular cyclohexyloxy, is preferred. [0011] Examples of C 2-C20acyl are formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl, acryloyl, methacryloyl and benzoyl. C1-C8Alkanoyl, C3-C8alkenyl and benzoyl are preferred. [0012] An example of C7-C12aryloxycarbonyl is phenyloxycarbonyl. [0013] A preferred example of C6-C10aryl is phenyl. 35 [0014] According to a preferred embodiment X 1 and X2 independently of one another are C 1-C4alkoxy and X3 is -OH. [0015] According to a particular preferred embodiment component (II) is a hyperbranched polycarbonate obtainable by the reaction of (a) a compound of the formula 40 H5C2-C-[CH2-O-CH2CH2-OH]3 (b) a compound of the formula 45 50 and (c) a compound of the formula 55 3 EP 2 876 126 A1 5 [0016] The compounds of components (I) and (II) are known, to a great extend commercially available and can be 10 prepared according to known methods. [0017] The compound 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methylphenol corresponds to the following structure: 15 20 [0018] The compound 3-[3-(2H-benzotriazo-2-yl)-5-t-butyl-4-hydroxybenzyl]propanoic acid C7-C9alkyl ester corre- sponds to the structure shown below. 25 30 [0019] A further embodiment of the present invention is a composition containing (A) an organic material susceptible to degradation induced by light, heat or oxidation and (B) the stabilizer mixture as defined above. [0020] Examples of organic materials which can be stabilized are: 35 1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-meth- ylpent-1-ene, polyvinylcyclohexane, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for instance of cyclopentene or norbornene, polyethylene (which optionally can be crosslinked), for example high density poly- ethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high density and ultrahigh 40 molecular weight polyethylene (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE). Polyolefins, i.e. the polymers of monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different, and especially by the following, methods: 45 a) radical polymerisation (normally under high pressure and at elevated temperature). b) catalytic polymerisation using a catalyst that normally contains one or more than one metal of groups IVb, Vb, Vlb or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either π- or σ-coordinated. 50 These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(III) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium. The catalysts can be used by themselves in the polymerisation or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups la, IIa and/or IIIa of the Periodic Table. The activators may be modified conveniently 55 with further ester, ether, amine or silyl ether groups. These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC). 2. Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyisobutylene, poly- 4 EP 2 876 126 A1 propylene with polyethylene (for example PP/HDPE, PP/LDPE) and mixtures of different types of polyethylene (for example LDPE/HDPE). 3. Copolymers of monoolefins and diolefins with each other or with other vinyl monomers, for example ethylene/pro- 5 pylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene/but-1-ene copolymers, propylene/isobutylene copolymers, ethylene/but-1-ene copolymers, eth- ylene/hexene copolymers, ethylene/methylpentene copolymers, ethylene/heptene copolymers, ethylene/octene co- polymers, ethylene/vinylcyclohexane copolymers, ethylene/cycloolefin copolymers (e.g.
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