US2003199618A1PendingUtilityA1
Stabilizer mixtures
Priority: May 31, 2000Filed: May 22, 2001Published: Oct 23, 2003
Est. expiryMay 31, 2020(expired)· nominal 20-yr term from priority
Inventors:Francois Gugumus
C08K 5/3462C08K 5/3477C08K 5/3435C09K 15/30C08K 5/34922C08K 5/353C08K 5/5419C08K 5/00
48
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Claims
Abstract
A stabilizer mixture containing the components (A), (B) and (C) wherein component (A) is for example a compound of the formula (A-1) wherein A 1 is hydrogen or C 1 -C 4 alkyl, A 2 is a direct bond or C 1 -C 10 alkylene, and n 1 is a number from 2 to 50; component (B) is a low molecular weight sterically hindered amine compound containing a group of the formula (I) or (II); and component (C) is a high molecular weight sterically hindered amine compound containing a group of the formula (I); with the proviso that components (A), (B) and (C) are different.
Claims
exact text as granted — not AI-modified1 . A stabilizer mixture containing the components (A), (B) and (C) wherein component (A) is
a compound of the formula (A-1) wherein
A 1 is hydrogen or C 1 -C 4 alkyl,
A 2 is a direct bond or C 1 -C 10 alkylene, and
n 1 is a number from 2 to 50;
at least one compound of the formulae (A-2-a) and (A-2-b) wherein
n 2 and n 2 * are a number from 2 to 50;
a compound of the formula (A-3) wherein
A 3 and A 4 independently of one another are hydrogen or C 1 -C 8 alkyl, or A 3 and A 4 together form a C 2 -C 14 alkylene group, and the variables n 3 independently of one another are a number from 1 to 50; or
a compound of the formula (A-4) wherein
n 4 is a number from 2 to 50,
A 5 is hydrogen or C 1 -C 4 alkyl,
the radicals A 6 and A 7 independently of one another are C 1 -C 4 alkyl or a group of the formula (a-I)
wherein A 8 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,
with the proviso that at least 50% of the radicals A 7 are a group of the formula (a-I); component (B) is a low molecular weight sterically hindered amine compound containing a group of the formula (I) or (II); and
component (C) is a high molecular weight sterically hindered amine compound containing a group of the formula (I); with the proviso that components (A), (B) and (C) are different.
2 . A stabilizer mixture according to claim 1 wherein component (B) is
a compound of the formula (B-1)
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 1, 2 or 4,
if m 1 is 1, E 2 is C 1 -C 25 alkyl,
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;
a compound of the formula (B-2)
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 ;
a compound of the formula (B-3)
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 ;
a compound of the formula (B-4)
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;
a compound of the formula (B-5)
wherein
the radicals E 16 independently of one another have one of the meanings of E 1 ;
a compound of the formula (B-6)
in which
E 17 is C 1 -C 24 alkyl, and
E 18 has one of the meanings of E 1 ;
a compound of the formula (B-7)
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 ;
a compound of the formula (B-8)
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;
a compound of the formula (B-9)
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; or
a compound of the formula (B-10)
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).
3 . A stabilizer mixture according to claim 1 wherein component (C) is
a compound of the formula (C-1)
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);
a compound of the formula (C-2)
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 ;
a compound of the formula (C-3)
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;
a compound of the formula (C-4)
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;
a compound of the formula (C-5)
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; or
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 .
4 . A stabilizer mixture according to claim 1 wherein
A 1 is hydrogen or methyl,
A 2 is a direct bond or C 2 -C 6 alkylene, and
n 1 is a number from 2 to 25;
n 2 and n 2 * are a number from 2 to 25;
A 3 and A 4 independently of one another are hydrogen or C 1 -C 4 alkyl, or A 3 and A4 together form a C 9 -C 13 alkylene group, and
the variables n 3 independently of one another are a number from 1 to 25; n 4 is a number from 2 to 25,
A 5 and A 6 independently of one another are C 1 -C 4 alkyl, and
A 7 is C 1 -C 4 alkyl or a group of the formula (a-I)
with the proviso that at least 50% of the radicals A 7 are a group of the formula (a-I).
5 . A stabilizer mixture according to claim 2 wherein
m 1 is 1, 2 or 4,
if m 1 is 1, 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.
6 . A stabilizer mixture according to claim 3 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.
7 . A stabilizer mixture according to claim 1 wherein
component (A) is a compound of the formula (A-1-a), (A-2-a), (A-2-b), (A-3-a) or (A-4-a);
wherein n 1 is a number from 2 to 20; wherein n 2 and n 2 * are a number from 2 to 20; wherein the variables n 3 independently of one another are a number from 1 to 20; wherein n 4 is a number from 2 to 20, and at least 50% of the radicals A 7 are a group of the formula (a-I) wherein A 8 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 the remaining radicals A 7 are ethyl;
component (B) is a compound of the formula (B-1-a), (B-1-b), (B-1-c), (B-1-d), (B-2-a), (B-3-a), (B-3-b), (B-4-a), (B-4-b), (B-5), (B-6-a), (B-7), (B-8-a), (B-9-a), (B-9-b), (B-9-c) or (B-10-a);
wherein 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; in which two of the radicals E 7 are —COO—C 13 H 27 and two of the radicals E 7 are and E 8 has one of the meanings of E 1 ; wherein E 12 has one of the meanings of E 1 ; wherein E 13 has one of the meanings of E 1 ; wherein E 16 has one of the meanings of E 1 ; wherein 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 E 23 has one of the meanings of E 1 ; wherein E 25 has one of the meanings of E 1 ; wherein E 29 has one of the meanings of E 1 ;
component (C) 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);
wherein b 1 is a number from 2 to 20 and 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; wherein R 13 has one of the meanings of R 6 , wherein b 2 is a number from 2 to 20 and R 16 has one of the meanings of R 6 ; wherein b 3 is a number from 1 to 20 and R 18 has one of the meanings of R 6 ; wherein b 4 is a number from 1 to 20 and R 30 has one of the meanings of R 6 ;
a product (C-6-a) obtainable by reacting a product, obtained by reaction of a polyamine of the formula (C-6-1-a) with cyanuric chloride, with a compound of the formula (C-6-2-a)
in which R 32 has one of the meanings of R 6 .
8 . A stabilizer mixture according to claim 1 wherein A 8 is hydrogen, C 1 -C 4 alkyl, C 1 -C 10 alkoxy, cyclohexyloxy, allyl, benzyl or acetyl.
9 . A stabilizer mixture according to claim 2 wherein 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.
10 . A stabilizer mixture according to claim 3 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.
11 . A stabilizer mixture according to claim 7 wherein A 8 , 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.
12 . A stabilizer mixture according to claim 7 wherein component (A) is a compound of the formula (A-1-a) wherein n 1 is a number from 2 to 20, or a compound of the formula (A-2-a) or (A-2-b) wherein n 2 and n 2 * are a number from 2 to 20, component (B) is a compound of the formula (B-1-b) wherein E 1 is hydrogen and component (C) is a compound of the formula (C-1-a) wherein b 1 is a number from 2 to 20 and R 6 is hydrogen, or a compound of the formula (C-1-b) wherein R 6 is hydrogen or propoxy and b 1 is a number from 2 to 20, or a compound of the formula (C-1-d) wherein R 6 is hydrogen or methyl and b 1 is a number from 2 to 20, or a compound of the formula (C-2-a) wherein R 13 is methyl, or a compound of the formula (C-3-a) wherein R 16 is hydrogen and b 2 is a number from 2 to 20, or a compound of the formula (C-4-a) wherein R 18 is hydrogen and b 3 is a number from 1 to 20, or a product (C-6-a).
13 . A stabilizer mixture according to claim 7 wherein component (A) is a compound of the formula (A-1-a) wherein n 1 is a number from 2 to 20, or a compound of the formula (A-2-a) or (A-2-b) wherein n 2 and n 2 * are a number from 2 to 20, component (B) is a compound of the formula (B-1-b) wherein E 1 is hydrogen and component (C) is a compound of the formula (C-1-a) wherein b 1 is a number from 2 to 20 and R 6 is hydrogen.
14 . A stabilizer mixture according to claim 7 wherein
component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-1-b) with E 1 being hydrogen and component (C) is a compound of the formula (C-1-a) with R 6 being hydrogen; or
component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-1-b) with E 1 being octyloxy and component (C) is a compound of the formula (C-1-a) with R 6 being hydrogen; or
component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-3-a) with E 12 being hydrogen and component (C) is a compound of the formula (C-1-a) with R 6 being hydrogen; or
component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-10-a) with E 29 being hydrogen and component (C) is a compound of the formula (C-1-a) with R 6 being hydrogen; or
component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-1-b) with E 1 being methyl and component (C) is a compound of the formula (C-2-a) with R 13 being 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 .
20 . A stabilizer mixture containing
(1) a component (AA-1) or (AA-2), and (2) a component (B) or (C);
component (AA-1) is a compound of the formula (AA-1-I) or (AA-1-II)
wherein n 100 is a number from 1 to 3; the radicals R 101 independently of one another are C 2 -C 18 alkylene, C 4 -C 8 alkenylene, C 4 -C 20 monooxaalkylene, C 4 -C 20 polyoxaalkylene, C 5 -C 8 cycloalkylene, C 7 -C 10 cycloalkylene-dialkylene, C 8 -C 20 phenylene-dialkylene or a group of the formula m 100 is an integer from 2 to 10; X 100 is a group —O— or —NR 105 —; Y 100 is C 2 -C 12 alkylene, C 4 -C 12 alkylene interrupted by one or two —O— or —NH— groups; cyclohexylene, cyclohexylene-dimethylene, phenylene or phenylene-Z 100 -phenylene with Z 100 being —O—, —CH 2 — or —SO 2 —; the radicals R 102 independently of one another are a direct bond, C 1 -C 18 alkylene, C 2 -C 6 alkenylene, C 5 -C 8 cycloalkylene, C 5 -C 8 cycloalkenylene, phenylene, C 7 -C 12 phenylenealkylene or a group of the formula p 100 is 1 or 2; E 100 is hydrogen, C 1 -C 8 alkyl, cyclohexyl, benzyl or an acyl group of the formula R 107 —CO—, R 108 —O—CO— or (R 109 )(R 110 )N—CO—; E′ 100 is a group R 111 O— or (R 112 )(R 113 )N—; R 103 is hydrogen, C 1 -C 6 alkyl, C 2 -C 7 alkoxymethyl, phenoxymethyl or tolyloxymethyl, R 104 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; R 105 is hydrogen, C 1 -C 12 alkyl, cyclohexyl, phenyl, benzyl, phenylethyl or C 1 -C 8 acyl; R 106 is C 2 -C 12 alkylene, C 4 -C 8 alkenylene or xylylene; R 107 is C 1 -C 12 alkyl, C 2 -C 5 alkenyl, C 5 -C 8 cycloalkyl, phenyl, C 7 -C 12 phenylalkyl or a group of the formula (AA-1-III) R 108 is C 1 -C 12 alkyl, allyl, cyclohexyl or phenyl; R 109 is hydrogen, C 1 -C 8 alkyl, allyl, cyclohexyl, phenyl or C 7 -C 10 alkylphenyl, R 110 is C 1 -C 8 alkyl, allyl, cyclohexyl, phenyl or C 7 -C 10 alkylphenyl; or R 109 and R 110 together with the N atom to which they are attached form a 5-membered to 7-membered heterocyclic ring; R 111 is C 1 -C 12 alkyl, C 3 -C 5 alkenylmethyl, C 5 -C 8 cyloalkyl, phenyl, C 7 -C 10 alkylphenyl, C 7 -C 12 phenylalkyl, C 3 -C 12 alkoxyalkyl, a group —(CH 2 CH 2 O) m100 —CH 3 , a group of the formula (AA-1-III) or a group of the formula (AA-1-IV); R 112 is C 1 -C 12 alkyl, allyl, cyclohexyl, phenyl, benzyl, C 3 -C 12 alkoxyalkyl, C 4 -C 12 dialkylaminoalkyl, a group of the formula (AA-1-III) or a group of the formula (AA-1-V); R 113 is hydrogen, C 1 -C 12 alkyl, allyl, cyclohexyl or a group of the formula (III); with the proviso that at least one of the radicals R 101 , R 102 , E 100 and E′ 100 contains a group of the formula with the proviso that the repeating units in each of the formulae (AA-1-I) and (AA-1-II) can be identical or different;
component (AA-2) is a compound of the formula (AA-2-I)
in which n 200 and are independently of one another a number from 1 to 50;
R 201 is hydrogen or C 1 -C 4 alkyl;
X 201 is —O— or >N—R 202 ;
R 202 is hydrogen, C 1 -C 12 alkyl, cyclohexyl, phenyl, benzyl, phenylethyl or C 1 -C 8 acyl;
Y 201 is C 1 -C 4 alkyl or a group of the formula (AA-2-II);
R 203 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;
Z 200 is ethylene or a group of the formula (AA-2-III)
R 204 is hydrogen or C 1 -C 4 alkyl;
X 202 has one of the meanings of X 201 ;
Y 202 is C 1 -C 18 alkyl or a group of the formula (AA-2-II);
with the provisos that the repeating units in the formula (AA-2-I) have a block or random distribution and that each of the repeating units
and —Z 200 —
in the formula (AA-2-I) can be identical or different, and
with the proviso that at least 2% of the repeating units in the formula (AA-2-I) contain a group of the formula (AA-2-II);
component (B) is a compound of the formula (B-1)
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 is1, 2 or 4,
if m 1 is 1, E 2 is C 1 -C 25 alkyl,
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;
a compound of the formula (B-2)
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 ;
a compound of the formula (B-3)
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 ;
a compound of the formula (B-4)
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;
a compound of the formula (B-5)
wherein
the radicals E 16 independently of one another have one of the meanings of E 1 ;
a compound, of the formula (B-6)
in which
E 17 is C 1 -C 24 alkyl, and
E 18 has one of the meanings of E 1 ;
a compound of the formula (B-7)
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 ;
a compound of the formula (B-8)
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;
a compound of the formula (B-9)
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; or
a compound of the formula (B-10)
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);
component (C) is a compound of the formula (C-1)
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);
a compound of the formula (C-2)
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 ;
a compound of the formula (C-3)
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;
a compound of the formula (C-4)
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;
a compound of the formula (C-5)
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; or
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 .
21 . A stabilizer mixture according to claim 20 wherein
n 100 is a number from 1 to 3;
R 101 is C 2 -C 12 alkylene, C 4 -C 20 monooxaalkylene, C 4 -C 20 polyoxaalkylene or a group of the formula
R 102 is a direct bond, C 1 -C 12 alkylene, C 2 -C 12 alkenylene or phenylene;
E 100 is hydrogen or a group R 107 —CO—;
E′ 100 is a group R 111 O—;
R 103 is hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkoxymethyl, phenoxymethyl or tolyloxymethyl;
R 104 is hydrogen, C 1 -C 4 alkyl, acetyl, allyl or benzyl;
R 107 is C 1 -C 6 alkyl or phenyl;
R 111 is C 1 -C 12 alkyl or a group of the formula (AA-1-III) or (AA-1-IV); and
n 200 and n 201 are independently of one another a number from 1 to 20;
R 201 and R 204 are independently of one another hydrogen or C 1 -C 4 alkyl;
X 201 and X 202 are —O—; and
Z 200 is ethylene or a group of the formula (AA-2-III) and
Y 201 and Y 202 are independently of one another C 1 -C 4 alkyl or a group of the formula (AA-2-II).
22 . A stabilizer mixture according to claim 20 wherein component (AA-1) is a compound of the formula (AA-1-II) in which
n 100 is a number from 1 to 3;
R 101 is a group of the formula
R 102 is C 1 -C 4 alkylene, C 2 -C 4 alkenylene or phenylene;
E′ 100 is a group R 111 O—; and
R 111 is a group of the formula (AA-1-III).
23 . A stabilizer mixture according to claim 20 wherein component (AA-1) is a compound of the formula (AA-1-II-1), (AA-1-II-2), (AA-1-II-3), (AA-1-II-4) or (AA-1-II-5).
wherein R 104 is hydrogen, methyl, C 1 -C 8 alkoxy or cyclohexyloxy.
24 . A stabilizer mixture according to claim 20 wherein component (AA-2) is a compound of the formula (AA-2-I-1), (AA-2-I-2) or (AA-2-I-3).
in which n 200 and n 201 are independently of one another a number from 1 to 20, and at least 50% of the radicals Y 202 are a group of the formula
with R 203 being hydrogen, methyl, C 1 -C 8 alkoxy or cyclohexyloxy,
and the remaining radicals Y 202 are ethyl;
wherein n 200 and n 201 are independently of one another a number from 1 to 20, R 201 is hydrogen or methyl, and R 203 is hydrogen, methyl, C 1 -C 8 alkoxy or cyclohexyloxy;
wherein the sum of n 200 and n 201 is a number from 2 to 20, and R 203 is hydrogen, methyl, C 1 -C 8 alkoxy or cyclohexyloxy.
25 . A stabilizer mixture according to claim 20 containing
(1) a compound of the formula
with the sum of n 200 and n 201 being a number from 2 to 20, and
(2) a compound of the formula
26 . A composition comprising an organic material subject to degradation induced by light, heat or oxidation and a stabilizer mixture according to claim 20 .
27 . 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 20.Join the waitlist — get patent alerts
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