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EP0389429A2
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EP
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Azo compounds containing hindered amine moieties with low basicity
Assignee: BASF Schweiz AG
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Filing: 1990-03-13
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Granted: —
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Expires: 2010-03-13
Abstract
Abstract Compounds which contain an azo group as well as a hindered amine light stabilizer moiety of low basicity function as free radical polymerization initiators and provide a polymer containing a hindered amine stabilizer chemically bonded to said polymer. The low basicity of the instant compounds prevents interaction with acid catalysts used in some polymerization systems.
Inventors
- 👤 Ramanathan Ravichandran
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-08 23:07
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/92; C07D211/94; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/56; C07D211/58; C07D211/60; C07D211/62; C07D211/66; C08; C08F; C08F4/00; C08F4/04; C08F8/00; C08F8/30; C08F8/32; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C08F2800/00; C08F2800/20
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
284 words
A compound having in the same molecule a hindered amine moiety of low basicity and an azo group, said compound having the formula I E₁-N=N-E₂ (I) where E₁ is a radical of the formula where R₁ and R₂ are independently alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 20 carbon atoms, or R₁ and R₂ together are alkylene of 2 to 10 carbon atoms, or one of R₁ and R₂ is a group of formula II Y is -CN, -N₃, -COOT₁, -CONH₂, -OT₁, -ST₁, -OOH or -OH, G₁ and G₂ are independently alkyl of 1 to 4 carbon atoms, or G₁ and G₂ together are pentamethylene, X is -O-, -NH-, -NT₁- or T is formyl, -OT₁ or -OCOT₂, where T₁ is alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkenyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, a radical of a saturated or unsaturated bicyclic or tricyclic hydrocarbon of 7 to 12 carbon atoms or aryl of 6 to 10 carbon atoms or said aryl substituted by alkyl, T₂ is alkyl of 1 to 18 carbon atoms, alkoxy of 1 to 18 carbon atoms, phenyl or said phenyl substituted by hydroxy, alkyl or alkoxy; or amino or said amino mono- or disubstituted by alkyl or phenyl, and E₂ has the same meaning as E₁ or E₂ is alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms or aralkyl of 7 to 20 carbon atoms, with the proviso that one of E₁ or E₂ must contain a group having a present.
Claim 2
Dependent Claim
284 words
A compound having in the same molecule a hindered amine moiety of low basicity and an azo group, said compound having the formula I E₁-N=N-E₂ (I) where E₁ is a radical of the formula where R₁ and R₂ are independently alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 20 carbon atoms, or R₁ and R₂ together are alkylene of 2 to 10 carbon atoms, or one of R₁ and R₂ is a group of formula II Y is -CN, -N₃, -COOT₁, -CONH₂, -OT₁, -ST₁, -OOH or -OH, G₁ and G₂ are independently alkyl of 1 to 4 carbon atoms, or G₁ and G₂ together are pentamethylene, X is -O-, -NH-, -NT₁- or T is formyl, -OT₁ or -OCOT₂, where T₁ is alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkenyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, a radical of a saturated or unsaturated bicyclic or tricyclic hydrocarbon of 7 to 12 carbon atoms or aryl of 6 to 10 carbon atoms or said aryl substituted by alkyl, T₂ is alkyl of 1 to 18 carbon atoms, alkoxy of 1 to 18 carbon atoms, phenyl or said phenyl substituted by hydroxy, alkyl or alkoxy; or amino or said amino mono- or disubstituted by alkyl or phenyl, and E₂ has the same meaning as E₁ or E₂ is alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms or aralkyl of 7 to 20 carbon atoms, with the proviso that one of E₁ or E₂ must contain a group having a present.
Claim 3
Dependent Claim
13 words
A compound according to claim 1 wherein E₁ and E₂ are the same.
Claim 4
Dependent Claim
13 words
A compound according to claim 1 wherein G₁ and G₂ are each methyl.
Claim 5
Dependent Claim
19 words
A compound according to claim 1 wherein R₁ and R₂ are each alkyl of 1 to 4 carbon atoms.
Claim 6
Dependent Claim
13 words
A compound according to claim 4 wherein R₁ and R₂ are each methyl.
Claim 7
Dependent Claim
10 words
A compound according to claim 1 wherein Y is -CN.
Claim 8
Dependent Claim
12 words
A compound according to claim 1 wherein X is -O-, -NH- or
Claim 9
Dependent Claim
12 words
A compound according to claim 7 wherein X is -O- or -NH-.
Claim 10
Dependent Claim
33 words
A compound according to claim 1 wherein T is formyl or -OT₁, where T₁ is alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 3 carbon atoms, propargyl, alpha-methylbenzyl or cyclohexyl.
Claim 11
Dependent Claim
44 words
A compound of formula I according to claim 1 wherein E₁ is a group wherein X is -O- or -NH- and T₁ is alkyl of 1 to 12 carbon atoms or is cyclohexyl and E₂ is the same as E₁ or is tertiary butyl.
Claim 12
Dependent Claim
10 words
The compound according to claim 1 which is di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) 4,4′-azobis(4-cyanovalerate).
Claim 13
Dependent Claim
10 words
The compound according to claim 1 which is di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) 4,4′-azobis(4-cyanovalerate).
Claim 14
Dependent Claim
9 words
The compound according to claim 1 which is N,N′-di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-4,4′-azobis(4-cyanovaleramide).
Claim 15
Dependent Claim
59 words
A process of preparing a light-stable homo- or copolymer containing a hindered amine light stabilizer moiety chemically bonded to the backbone of said polymer which process comprises polymerizing one or more ethylenically unsaturated monomers capable of being polymerized by free radicals in the presence of an effective initiating amount of a compound of formula I according to claim 1.
Claim 16
Dependent Claim
20 words
A polymer stabilized against the deleterious effects of actinic light which is produced by the process according to claim 14.
Claim 17
Dependent Claim
24 words
A composition stabilized against the deleterious effects of actinic light which composition contains a stabilized polymer made by the process according to claim 14.
Claim 18
Dependent Claim
28 words
A composition stabilized against the deleterious effects of actinic light which comprises (a) a polymer, and (b) an effective stabilizing amount of a compound according to claim 1.
Claim 19
Dependent Claim
12 words
A composition according to claim 17 wherein the polymer is a polyolefin.
Claim 20
Dependent Claim
11 words
A composition according to claim 18 wherein the polyolefin is polypropylene.
Claim 21
Dependent Claim
26 words
A composition according to claim 17 wherein the polymer is a coating system based on alkyd, acrylic, acrylic-alkyd, polyester, epoxide, urethane, polyamide, vinyl or epoxy-polyester resins.
Claim 22
Dependent Claim
12 words
A composition according to claim 17 wherein component (b) is di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) 4,4′-azobis(4-cyanovalerate).
Claim 23
Dependent Claim
12 words
A composition according to claim 17 wherein component (b) is di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) 4,4′-azobis(4-cyanovalerate).
Claim 24
Dependent Claim
15 words
A composition according to claim 20 which contains a UV absorber or additional light stabilizer.
Claim 25
Dependent Claim
34 words
A composition according to claim 17 wherein the polymer is an unsaturated elastomer which is polybutadiene, polyisoprene, styrene-butadiene copolymer or block copolymer, ethylene-propylene terpolymer, isoprene-isobutylene copolymer, acrylonitrile-butadiene copolymer, or styrene-isoprene copolymer or block copolymer.
Claim 26
Dependent Claim
22 words
A composition according to claim 24 wherein the elastomer is styrene-butadiene copolymer or block copolymer, styrene-isoprene copolymer or block copolymer or polybutadiene.
Claim 27
Dependent Claim
15 words
A composition according to claim 17 wherein the component (b) is grafted to component (a).
Claim 28
Dependent Claim
34 words
A method for stabilizing an organic material against oxidative, thermal or actinic degradation which comprises incorporating into said organic material an effective stabilizing amount of a compound of formula I according to claim 1.
References Cited (Backward Citations)
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