US2009105379A1PendingUtilityA1
Stabilizer mixtures
Est. expiryMay 31, 2020(expired)· nominal 20-yr term from priority
Inventors:Francois Gugumus
C08K 5/34C08K 5/5419C08K 5/005C08K 5/34926C08K 5/34922C09K 15/26C08K 5/3435C08K 5/353C08K 5/3477C08K 5/3462
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Claims
Abstract
A stabilizer mixture containing the components (A) and (B) 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; and component (B) is formed by two different low molecular weight sterically hindered amine compounds containing a group of the formula (I) or (II); with the proviso that components (A) and (B) are different.
Claims
exact text as granted — not AI-modified1 . A stabilizer mixture containing the components (A) and (B) 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); and component (B) is formed by two different low molecular weight sterically hindered amine compounds containing a group of the formula (I) or (II);
with the proviso that components (A) and (B) are different.
2 . A stabilizer mixture according to claim 1 wherein the two different compounds of component (B) are selected from the group consisting of the classes
β-1) 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;
β-2) 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 ;
β-3) 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 ;
β- 4 ) 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;
β-5) a compound of the formula (B-5)
wherein
the radicals E 16 independently of one another have one of the meanings of E 1 ;
β-6) 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 ;
β-7) 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 ;
β-8) 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;
β-9) 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;
β-10) 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); or
β-11) a compound of the formula (B-11)
in which
E 31 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,
E 32 is C 3 -C 10 alkylene,
E 33 has one of the meanings of E 1 , and
m 3 is a number from 2 to 6.
3 . 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 A 4 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).
4 . 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;
E 30 is C 2 -C 8 alkylene; and
E 31 is C 1 -C 4 alkyl,
E 32 is C 3 -C 6 alkylene, and
m 3 is a number from 2 to 6.
5 . 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; and
component (B) is formed by two different compounds selected from the group consisting of compounds of the formulae (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), (B-10-a) and (B-11-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 ;
wherein m 3 is a number from 2 to 6 and E 33 has one of the meanings of E 1 .
6 . 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.
7 . 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 , E 29 and E 33 are hydrogen, C 1 -C 4 alkyl, C 1 -C 10 alkoxy, cyclohexyloxy, allyl, benzyl or acetyl.
8 . A stabilizer mixture according to claim 5 wherein A 8 , E 1 , E 8 , E 12 , E 13 , E 16 , E 18 , E 22 , E 23 , E 25 , E 29 and E 33 are hydrogen or methyl and E 1 additionally is C 1 -C 8 alkoxy.
9 . A stabilizer mixture according to claim 5 wherein one of the two different compounds forming component (B) is a compound of the formula (B-1-b) with E 1 being hydrogen.
10 . A stabilizer mixture according to claim 5 wherein
component (A) is a compound of the formula (A-1-a) with n 1 being 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; and one of the two different compounds forming component (B) is a compound of the formula (B-1-b) with E 1 being hydrogen.
11 . A stabilizer mixture according to claim 5 wherein component (A) is a compound of the formula (A-1-a) with n 1 being 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;
one of the two different compounds forming component (B) is a compound of the formula (B-1-b) with E 1 being hydrogen; and the other of the two different compounds forming component (B) is a compound of the formula (B-1-a) with E 1 being hydrogen, (B-1-b) with E 1 being methyl, (B-1-d) with E 1 being hydrogen or methyl, (B-3-a) with E 12 being hydrogen, (B-3-b) with E 12 being hydrogen, (B-4-b) with E 13 being hydrogen, (B-5) with E 16 being hydrogen, (B-6-a) with E 18 being hydrogen or methyl, (B-8-a) with E 23 being methyl, (B-9-c) with E 25 being hydrogen or methyl, (B-10-a) with E 29 being hydrogen, or (B-11-a) with E 33 being hydrogen.
12 . A stabilizer mixture according to claim 5 wherein
component (A) is a compound of the formula (A-1-a) with n 1 being 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 (B-1-b) wherein E 1 is octyloxy; or component (A) is a compound of the formula (A-1-a) with n 1 being 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 (B-3-a) wherein E 12 is hydrogen; or component (A) is a compound of the formula (A-1-a) with n 1 being 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 (B-1-d) wherein E 1 is hydrogen; or component (A) is a compound of the formula (A-1-a) with n 1 being 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 (B-1-a) wherein E 1 is hydrogen; or component (A) is a compound of the formula (A-1-a) with n 1 being a number from 2 to 20, component (B) is a compound of the formula (B-1-b) wherein E 1 is methyl, and component (C) is a compound of the formula (B-1-d) wherein E 1 is methyl.
13 . A composition comprising an organic material subject to degradation induced by light, heat or oxidation and a stabilizer mixture according to claim 1 .
14 . A composition according to claim 13 wherein the organic material is a synthetic polymer.
15 . A composition according to claim 13 wherein the organic material is a polyolefin.
16 . A composition according to claim 13 wherein the organic material is polyethylene, polypropylene, a polyethylene copolymer or a polypropylene copolymer.
17 . 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 .Join the waitlist — get patent alerts
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