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EP0389428A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

N,N-Bis(l-hydroxycarbyloxy-2,2,6,6-tetramethyl-piperidin-4-yl) amino triazines and stabilized compositions

Assignee: Novartis AG
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Filing: 1990-03-13
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Granted: —
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Expires: 2010-03-13
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Abstract

Abstract Triazines substituted with an N,N-bis(1-hydrocarby­loxy-2,2,6,6-tetramethylpiperidin-4-yl)amino moiety are effective stabilizers for polymer compositions against the deleterious effects of actinic light.

Inventors

  • 👤 Ramanathan Ravichandran
  • 👤 James P. Galbo

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-08 22:35
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/14; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477; C08K5/3492; C08K5/34926

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 444 words
A compound having formula I, II or III wherein G₁ and G₂ are independently alkyl of 1 to 4 carbon atoms, or G₁ and G₂ together are pentamethylene, R₁ is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, alkenyl of 2 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. R₂ and R₃ are independently -SR₅, -NR₆R₇, -NR₈-R₉-NR₁₀R₁₁, -OR₄, -O(R₁₂0) n R₁₃, R₄ has the same meaning as R₁, R₅ has the same definitions as R₁ and additionally R₅ is alkyl of 2 to 4 carbon atoms substituted by hydroxy, by alkoxy of 1 to 12 carbon atoms or by di(C₁-C₄-alkyl)amino, R₆ and R₈ are independently hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms or alkyl of 2 to 4 carbon atoms substituted by hydroxy, by alkoxy of 1 to 12 carbon atoms or by R₇ has the same meaning as R₆ or R₆ and R₇ together with N-atom to which they are linked for a 5-7 membered heterocyclic ring containing one or two nitrogen atoms or oxygen, R₉ is alkylene of 2 to 12 carbon atoms, R₁₀ and R₁₁ have independently of the same definition as R₆ or R₁₀ and R₁₁ together have the same definition as R₆ and R₇ together. R₁₂ is alkylene of 2 to 4 carbon atoms, R₁₃ is hydrogen, alkyl of 1 to 18 carbon atoms, phenyl or said phenyl substituted by alkyl of 1 to 12 carbon atoms or by n is an integer of 2 to 20, m is an integer of 2 to 4, X has the same meanings as R₂, T₁ is piperazinyl, -NR₁₄-(CH₂) a O(CH₂) b O(CH₂) a NR₁₄-, -NR₁₄-(CH₂) d -NR₁₄- or -NH-(CH₂) a -N-(CH₂) b -N[(CH₂) c -N] f H- wherein R₁₄ is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, alkanoyl of 2 to 18 carbon atoms, alkenoyl of 3 to 5 carbon atoms or benzoyl, a, b, c, d are independently 2 or 3, f is 0 or 1, T₂ and T₃ are independently hydrogen or alkyl of 1 to 6 carbon atoms, T₄ is a direct bond or a hydrocarbyl group of valence p, and p is' 2 or 3, with the proviso that when the compound is of formula III, R₁ is not alkyl.
Claim 2
Dependent Claim 444 words
A compound having formula I, II or III wherein G₁ and G₂ are independently alkyl of 1 to 4 carbon atoms, or G₁ and G₂ together are pentamethylene, R₁ is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, alkenyl of 2 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. R₂ and R₃ are independently -SR₅, -NR₆R₇, -NR₈-R₉-NR₁₀R₁₁, -OR₄, -O(R₁₂0) n R₁₃, R₄ has the same meaning as R₁, R₅ has the same definitions as R₁ and additionally R₅ is alkyl of 2 to 4 carbon atoms substituted by hydroxy, by alkoxy of 1 to 12 carbon atoms or by di(C₁-C₄-alkyl)amino, R₆ and R₈ are independently hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms or alkyl of 2 to 4 carbon atoms substituted by hydroxy, by alkoxy of 1 to 12 carbon atoms or by R₇ has the same meaning as R₆ or R₆ and R₇ together with N-atom to which they are linked for a 5-7 membered heterocyclic ring containing one or two nitrogen atoms or oxygen, R₉ is alkylene of 2 to 12 carbon atoms, R₁₀ and R₁₁ have independently of the same definition as R₆ or R₁₀ and R₁₁ together have the same definition as R₆ and R₇ together. R₁₂ is alkylene of 2 to 4 carbon atoms, R₁₃ is hydrogen, alkyl of 1 to 18 carbon atoms, phenyl or said phenyl substituted by alkyl of 1 to 12 carbon atoms or by n is an integer of 2 to 20, m is an integer of 2 to 4, X has the same meanings as R₂, T₁ is piperazinyl, -NR₁₄-(CH₂) a O(CH₂) b O(CH₂) a NR₁₄-, -NR₁₄-(CH₂) d -NR₁₄- or -NH-(CH₂) a -N-(CH₂) b -N[(CH₂) c -N] f H- wherein R₁₄ is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, alkanoyl of 2 to 18 carbon atoms, alkenoyl of 3 to 5 carbon atoms or benzoyl, a, b, c, d are independently 2 or 3, f is 0 or 1, T₂ and T₃ are independently hydrogen or alkyl of 1 to 6 carbon atoms, T₄ is a direct bond or a hydrocarbyl group of valence p, and p is' 2 or 3, with the proviso that when the compound is of formula III, R₁ is not alkyl.
Claim 3
Dependent Claim 13 words
A compound according to claim 1 wherein G₁ and G₂ are each methyl.
Claim 4
Dependent Claim 19 words
A compound according to claim 1 wherein R₁ is alkyl of 1 to 12 carbon atoms, cyclohexyl or alpha-methylbenzyl.
Claim 5
Dependent Claim 16 words
A compound according to claim 3 wherein R₁ is methyl, heptyl, octyl, nonyl, cyclohexyl or alpha-methylbenzyl.
Claim 6
Dependent Claim 18 words
A compound according to claim 1 wherein R₂ and R₃ are the same and are -SR₅, -NR₆R₇ or
Claim 7
Dependent Claim 17 words
6 A compound according to claim 1 wherein R₅ is alkyl of 1 to 18 carbon atoms,
Claim 8
Dependent Claim 36 words
A compound according to claim 1 wherein R₆ is hydrogen, alkyl of 1 to 18 carbon atoms, or a group or R₆ and R₇ together with the nitrogen atom to which they are attached are morpholino.
Claim 9
Dependent Claim 18 words
A compound according to claim 1 wherein T₁ is -NH(CH₂) a -N-(CH₂) b -N-[(CH₂) c -N] f H-.
Claim 10
Dependent Claim 20 words
A compound according to claim 1 wherein T₄ is a direct bond or alkylidene of 2 to 4 carbon atoms.
Claim 11
Dependent Claim 11 words
The compound according to claim 1 which is 2,4-bis [N,N-bis (1-cyclohexyloxy-2,2,6,6-tetramethylpiperi­din-4-yl)amino]-6-(N,N-dioctadecylamino)-s-triazine.
Claim 12
Dependent Claim 10 words
The compound according to claim 1 which is N,N′-­bis[2,4-bis[N,N-bis(1-cyclohexyloxy-2,2,6,6-tetramethyl­piperidin-4-yl)amino]-s-triazin-6-yl]-N,N′-dimethylhexa methylenediamine.
Claim 13
Dependent Claim 9 words
The compound according to claim 1 which is N,N′-Bis[2,4-bis[N,N-bis(1-octyloxy-2,2,6,6-tetramethyl­piperidin-4-yl)amino]-s-triazin-6-yl]-N,N′-dimethyl­hexamethylenediamine
Claim 14
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 15
Dependent Claim 12 words
A composition according to claim 13 wherein the polymer is a polyolefin.
Claim 16
Dependent Claim 11 words
A composition according to claim 14 wherein the polyolefin is polypropylene.
Claim 17
Dependent Claim 11 words
A composition according to claim 13 wherein component (b) is 2,4-bis[N,N-bis(1-cyclohexyloxy-2,2,6,6-­tetramethylpiperidin-4-yl)amino]-6-(N,N-dioctadecylamino)-­s-triazine.
Claim 18
Dependent Claim 27 words
A composition according to claim 13 wherein the polymer is a coating system based on alkyd, acrylic, acrylic alkyd, polyester, epoxide, urethane, polyamide, vinyl or epoxy-polyester resins.
Claim 19
Dependent Claim 15 words
A composition according to claim 17 which contains a UV absorber or additional light stabilizer.
Claim 20
Dependent Claim 31 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 according to claim 1.
Claim 21
Dependent Claim 1 words
2,4-Bis[N,N-bis(1-octyloxy-2,2,6,6-tetramethyl­piperidin-4-yl)amino]-6-chloro-s-triazine.
Claim 22
Dependent Claim 1 words
2,4-Bis[N,N-bis(1-octyloxy-2,2,6,6-tetramethyl­piperidin-4-yl)amino]-6-chloro-s-triazine.
Claim 23
Dependent Claim 1 words
2,4,-Bis[N,N-bis(1-cyclohexyloxy-2,2,6,6-tetra­methylpiperidin-4-yl)amino]-6-chloro-s-triazine.
Claim 24
Dependent Claim 1 words
2,4,-Bis[N,N-bis(1-cyclohexyloxy-2,2,6,6-tetra­methylpiperidin-4-yl)amino]-6-chloro-s-triazine.

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