Stabilizer mixtures

Abstract

A stabilizer mixture containing the components (I), (II) and (Ill) wherein component (I) is for example a compound of the formula (B-1-b) wherein E 1 is hydrogen; component (II) is for example a compound of the formula (B-0-a) wherein E 1 * is hydrogen; and component (III) is for example a compound of the formula (C-1-a) wherein bi is a number from 2 to 20 and R 6 is hydrogen; is useful for stabilizing an organic material against degradation induced by light, heat or oxidation.

1 . A stabilizer mixture containing the components (I), (II) and (III) wherein 
 component (1) is a compound of the formula (B-1), (B-2), (B-4), (B-5), (B-7), (B-8), (B-9) or (B-10),    component (II) is a compound of the formula (B-0), (B-3) or (B-6), and    component (III) is a compound of the formula (C-1), (C-2), (C-3), (C-4) or (C-5) or a product (C-6);                          in which    E 1 * has one of the meanings of E 1 , and    E 2 * is C 1 -C 25 alkyl;                          in which    E 1  is hydrogen, C 1 -C 8 alkyl, O., —OH, —CH 2 CN, C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, C 3 -C 6 alkenyl,    C 7 -C 9 phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; or C 1 -C 8 acyl,    m 1  is 2 or 4,    if m 1  is 2, E 2  is C 1 -C 14 alkylene or a group of the formula (b-I)                          wherein E 3  is C 1 -C 10 alkyl or C 2 -C 10 alkenyl, E 4  is C 1 -C 10 alkylene, and    E 5  and E 6  independently of one another are C 1 -C 4 alkyl, cyclohexyl or methylcyclohexyl, and    if m 1  is 4, E 2  is C 4 -C 10 alkanetetrayl;                          in which    two of the radicals E 7  are —COO-(C 1 -C 20 alkyl), and    two of the radicals E 7  are a group of the formula (b-II)                          with E 8  having one of the meanings of E 1 ;                          in which    E 9  and E 10  together form C 2 -C 14 alkylene,    E 11  is hydrogen or a group —Z 1 —COO—Z 2 ,    Z 1  is C 2 -C 14 alkylene, and    Z 2  is C 1 -C 24 alkyl, and    E 12  has one of the meanings of E 1 ;                          wherein    the radicals E 13  independently of one another have one of the meanings of E 1 ,    the radicals E 14  independently of one another are hydrogen or C 1 -C 12 alkyl, and E 15  is C 1 -C 10 alkylene or C 3 -C 10 alkylidene;                          wherein    the radicals E 16  independently of one another have one of the meanings of E 1 ;                          in which    E 17  is C 1 -C 24 alkyl, and    E 18  has one of the meanings of E 1 ;                          in which    E 19 , E 20  and E 21  independently of one another are a group of the formula (b-III)                          wherein E 22  has one of the meanings of E 1 ;                          wherein    the radicals E 23  independently of one another have one of the meanings of E 1 , and E 24  is hydrogen, C 1 -C 12 alkyl or C 1 -C 12 alkoxy;                          wherein    m 2  is 1, 2 or 3,    E 25  has one of the meanings of E 1 , and    when m 2  is 1, E 26  is a group                          when m 2  is 2, E 26  is C 2 -C 22 alkylene, and    when m 2  is 3, E 26  is a group of the formula (b-IV)                          wherein the radicals E 27  independently of one another are C 2 -C 12 alkylene, and the radicals E 28  independently of one another are C 1 -C 12 alkyl or C 5 -C 12 cycloalkyl;                          wherein    the radicals E 29  independently of one another have one of the meanings of E 1 , and    E 30  is C 2 -C 22 alkylene, C 5 -C 7 cycloalkylene, C 1 -C 4 alkylenedi(C 5 -C 7 cycloalkylene), phenylene or phenylenedi(C 1 -C 4 alkylene);                          in which    R 1 , R 3 , R 4  and R 5  independently of one another are hydrogen, C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl, C 1 -C 4 -alkyl-substituted C 5 -C 12 cycloalkyl, phenyl, phenyl which is substituted by —OH and/or C 1 -C 10 alkyl; C 7 -C 9 phenylalkyl, C 7 -C 9 phenylalkyl which is substituted on the phenyl radical by —OH and/or C 1 -C 10 alkyl; or a group of the formula (c-I)                          R 2  is C 2 -C 18 alkylene, C 5 -C 7 cycloalkylene or C 1 -C 4 alkylenedi(C 5 -C 7 cycloalkylene), or    the radicals R 1 , R 2  and R 3 , together with the nitrogen atoms to which they are bonded, perform a 5- to 10-membered heterocyclic ring, or    R 4  and R 5 , together with the nitrogen atom to which they are bonded, form a 5- to 10-membered heterocyclic ring,    R 6  is hydrogen, C 1 -C 8 alkyl, O., —OH, —CH 2 CN, C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, C 3 -C 6 alkenyl, C 7 -C 9 phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; or C 1 -C 8 acyl, and    b 1  is a number from 2 to 50,    with the proviso that at least one of the radicals R 1 , R 3 , R 4  and R 5  is a group of the formula (c-I);                          wherein    R 7  and R 11 , independently of one another are hydrogen or C 1 -C 12 alkyl,    R 8 , R 9  and R 10  independently of one another are C 2 -C 10 alkylene, and    X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7  and X 8  independently of one another are a group of the formula (c-II),                          in which R 12  is hydrogen, C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl, C 1 -C 4 alkyl-substituted C 5 -C 12 cycloalkyl, phenyl, —OH— and/or C 1 -C 10 alkyl-substituted phenyl, C 7 -C 9 phenylalkyl, C 7 -C 9 phenylalkyl which is substituted on the phenyl radical by —OH and/or C 1 -C 10 alkyl; or a group of the formula (c-I) as defined above, and    R 13  has one of the meanings of R 6 ;                          in which    R 14  is C 1 -C 10 alkyl, C 5 -C 12 cycloalkyl, C 1 -C 4 alkyl-substituted C 5 -C 12 cycloalkyl, phenyl or C 1 -C 10 alkyl-substituted phenyl,    R 15  is C 3 -C 10 alkylene,    R 16  has one of the meanings of R 6 , and    b 2  is a number from 2 to 50;                          in which    R 17  and R 21  independently of one another are a direct bond or a —N(X 9 )—CO—X 10 —CO—N(X 11 )— group, where X 9  and X 11  independently of one another are hydrogen, C 1 -C 8 alkyl, C 5 -C 12 cycloalkyl, phenyl, C 7 -C 9 phenylalkyl or a group of the formula (c-I),    X 10  is a direct bond or C 1 -C 4 alkylene,    R 18  has one of the meanings of R 6 ,    R 19 , R 20 , R 23  and R 24  independently of one another are hydrogen, C 1 -C 30 alkyl,    C 5 -C 12 cycloalkyl or phenyl,    R 22  is hydrogen, C 1 -C 30 alkyl, C 5 -C 12 cycloalkyl, phenyl, C 7 -C 9 phenylalkyl or a group of the formula (c-I), and    b 3  is a number from 1 to 50;                          in which    R 25 , R 26 , R 27 , R 28  and R 29  independently of one another are a direct bond or C 1 -C 10 alkylene,    R 30  has one of the meanings of R 6 , and    b 4  is a number from 1 to 50;    a product (C-6) obtainable by reacting a product, obtained by reaction of a polyamine of the formula (C-6-1) with cyanuric chloride, with a compound of the formula (C-6-2)                          in which    b′ 5 , b″ 5  and b′″ 5  independently of one another are a number from 2 to 12,    R 31  is hydrogen, C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl, phenyl or C 7 -C 9 phenylalkyl, and    R 32  has one of the meanings of R 6 .    
     
     
         2 . A stabilizer mixture according to  claim 1  wherein 
 m 1  is 2 or 4,  
 E 2 * is C 12 -C 20 alkyl,  
 if m 1  is 2, E 2  is C 2 -C 10 alkylene or a group of the formula (b-I)  
 E 3  is C 1 -C 4 alkyl,  
 E 4  is C 1 -C 6 alkylene, and  
 E 5  and E 6  independently of one another are C 1 -C 4 alkyl, and  
 if m 1  is 4, E 2  is C 4 -C 8 alkanetetrayl;  
 two of the radicals E 7  are —COO—(C 10 -C 15 alkyl), and  
 two of the radicals E 7  are a group of the formula (b-II);  
 E 9  and E 10  together form C 9 -C 13 alkylene,  
 E 11 , is hydrogen or a group —Z 1 —COO—Z 2 ,  
 Z 1  is C 2 -C 6 alkylene, and  
 Z 2  is C 10 -C 16 alkyl;  
 E 14  is hydrogen, and  
 E 15  is C 2 -C 6 alkylene or C 3 -C 5 alkylidene;  
 E 17  is C 10 -C 14 alkyl;  
 E 24  is C 1 -C 4 alkoxy;  
 m 2  is 1, 2 or 3,  
 when m 2  is 1, E 26  is a group  
                     
 when m 2  is 2, E 26  is C 2 -C 6 alkylene, and  
 when m 2  is 3, E 26  is a group of the formula (b-IV)  
 the radicals E 27  independently of one another are C 2 -C 6 alkylene, and  
 the radicals E 28  independently of one another are C 1 -C 4 alkyl or C 5 -C 8 cycloalkyl; and  
 E 30  is C 2 -C 8 alkylene.  
 
     
     
         3 . A stabilizer mixture according to  claim 1  wherein 
 R 1  and R 3  independently of one another are a group of the formula (c-I),  
 R 2  is C 2 -C 8 alkylene,  
 R 4  and R 5  independently of one another are hydrogen, C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl or a group of the formula (c-I), or the radicals R 4  and R 5 , together with the nitrogen atom to which they are bonded, form a 5- to 10-membered heterocyclic ring, and  
 b 1  is a number from 2 to 25;  
 R 7  and R 11  independently of one another are hydrogen or C 1 -C 4 alkyl,  
 R 8 , R 9  and R 10  independently of one another are C 2 -C 4 alkylene, and  
 X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7  and X 8  independently of one another are a group of the formula (c-II),  
 R 12  is hydrogen, C 1 -C 4 alkyl, C 5 -C 8 cycloalkyl or a group of the formula (c-I);  
 R 14  is C 1 -C 4 alkyl,  
 R 15  is C 3 -C 6 alkylene, and  
 b 2  is a number from 2 to 25;  
 R 17  and R 21  independently of one another are a direct bond or a group —N(X 9 )—CO—X 10 —CO—N(X 11 )—,  
 X 9  and X 11  independently of one another are hydrogen or C 1 -C 4 alkyl,  
 X 10  is a direct bond,  
 R 19  and R 23  are C 1 -C 25 alkyl or phenyl,  
 R 20  and R 24  are hydrogen or C 1 -C 4 alkyl,  
 R 22  is C 1 -C 25 alkyl or a group of the formula (c-I), and  
 b 3  is a number from 1 to 25;  
 R 25 , R 26 , R 27 , R 28  and R 29  independently of one another are a direct bond or C 1 -C 4 alkylene, and  
 b 4  is a number from 1 to 25;  
 b′ 5 , b″ 5  and b′″ 5  independently of one another are a number from 2 to 4, and  
 R 31  is hydrogen, C 1 -C 4 alkyl, C 5 -C 8 cycloalkyl, phenyl or benzyl.  
 
     
     
         4 . A Stabilizer mixture according to  claim 1  wherein 
 component (I) is a compound of the formula (B-1-b), (B-1-c), (B-1-d), (B-2-a), (B-4-a), (B-4-b), (B-5), (B-7), (B-8-a), (B-9-a), (B-9-b), (B-9-c) or (B-10-a);  
 component (II) is a compound of the formula (B-0-a), (B-3-a), (B-3-b) or (B-6-a); and  
 component (III) is a compound of the formula (C-1-a), (C-1-b), (C-1-c), (C-1-d), (C-2-a), (C-3-a), (C-4-a), (C-4-b), (C-4-c) or (C-5-a) or a product (C-6-a);  
                                                                           
 in which R 32  has one of the meanings of R 6 .  
 
     
     
         5 . A Stabilizer mixture according to  claim 1  wherein component (II) is a compound of the formula (B-0).  
     
     
         6 . A stabilizer mixture according to  claim 1  wherein 
 component (I) is a compound of the formula (B-1), (B-4), (B-5), (B-8), (B-9) or (B-10),  
 component (II) is a compound of the formula (B-0), (B-3) or (B-6), and  
 component (III) is a compound of the formula (C-1), (C-2), (C-3), (C-4) or (C-5) or a product (C-6).  
 
     
     
         7 . A Stabilizer mixture according to  claim 4  wherein 
 component (I) is a compound of the formula (B-1-b), (B-1-c), (B-4-a), (B-4-b), (B-5), (B-8-a), (B-9-b) or (B-10-a);  
 component (II) is a compound of the formula (B-0-a), (B-3-a), (B-3-b) or (B-6-a); and  
 component (III) is a compound of the formula (C-1-a), (C-1-b), (C-1-c), (C-1-d), (C-2-a), (C-3-a), (C-4-a), (C-4-b), (C-4-c) or (C-5-a) or a product (C-6-a).  
 
     
     
         8 . A stabilizer mixture according to  claim 1  wherein E 1 , E 1 *, E 8 , E 12 , E 13 , E 16 , E 18 , E 22 , E 23 , E 25  and E 29  are hydrogen, C 1 -C 4 alkyl, C 1 -C 10 alkoxy, cyclohexyloxy, allyl, benzyl or acetyl.  
     
     
         9 . A stabilizer mixture according to  claim 1  wherein R 6 , R 13 , R 16 , R 18 , R 30  and R 32  are hydrogen, C 1 -C 4 alkyl, C 1 -C 10 alkoxy, cyclohexyloxy, allyl, benzyl or acetyl.  
     
     
         10 . A stabilizer mixture according to  claim 4  wherein E 1 , E 1 *, E 8 , E 12 , E 13 , E 16 , E 18 , E 22 , E 23 , E 25 , E 29 , R 6 , R 13 , R 16 , R 18 , R 30  and R 32  are hydrogen or methyl and E 1  and R 6  additionally are C 1 -C 8 alkoxy.  
     
     
         11 . A stabilizer mixture according to  claim 4  wherein component (I) is a compound of the formula (B-1-b) wherein E 1  is hydrogen or methyl and component (II) is a compound of the formula (B-0-a) wherein E 1 * is hydrogen.  
     
     
         12 . A stabilizer mixture according to  claim 4  wherein component (I) is a compound of the formula (B-1-b) wherein E 1  is hydrogen or methyl, component (II) is a compound of the formula (B-0-a) wherein E 1 * is hydrogen and component (III) is a compound of the formula (C-1-a), (C-1-b) or (C-1-d) wherein R 6  is hydrogen or methyl.  
     
     
         13 . A stabilizer mixture according to  claim 4  wherein component (I) is a compound of the formula (B-1-b) wherein E 1  is hydrogen, component (II) is a compound of the formula (B-0-a) wherein E 1 * is hydrogen and component (III) is a compound of the formula (C-1-a) wherein R 6  is hydrogen.  
     
     
         14 . A stabilizer mixture according to  claim 4 , wherein component (I) is a compound of the formula (B-1-b) wherein E 1  is methyl, component (II) is a compound of the formula (B-6-a) wherein E 18  is methyl and component (III) is a compound of the formula (C-1-d) wherein R 6  is methyl, or a compound of the formula (C-2-a) wherein R 13  is methyl, or a compound of the formula (C-5-a) wherein R 30  is methyl.  
     
     
         15 . A composition comprising an organic material subject to degradation induced by light, heat or oxidation and a stabilizer mixture according to  claim 1 .  
     
     
         16 . A composition according to  claim 15  wherein the organic material is a synthetic polymer.  
     
     
         17 . A composition according to  claim 15  wherein the organic material is a polyolefin.  
     
     
         18 . A composition according to  claim 15  wherein the organic material is polyethylene, polypropylene, a polyethylene copolymer or a polypropylene copolymer.  
     
     
         19 . A method for stabilizing an organic material against degradation induced by light, heat or oxidation, which comprises incorporating into the organic material a stabilizer mixture according to  claim 1.