Patent EP0389427A2 successfully refreshed from Google Patents.
← Back to Patent Explorer
EP0389427A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Compounds containing both uv-absorber and 1-hydrocarbyloxy hindered amine moieties and stabilized compositions

Assignee: Novartis AG
•
Filing: 1990-03-13
•
Granted: —
•
Expires: 2010-03-13
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Compounds containing both a UV-absorbing moiety and a 1-hydrocarbyloxy hindered amine moiety are effective stabilizers for protecting polymer compositons against the deleterious effects of actinic light. The UV-absorbing moieties include the substituted 2H-benzotriazoles, s-triazines, acrylates, benzophenones, oxanilides and oxamides.

Inventors

  • 👤 Ramanathan Ravichandran
  • 👤 James P. Galbo

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-09 01:34
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/12; C07D211/00; C07D211/92; C07D211/94; C07D401/14; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C08K5/3467; C08K5/3477; C08K5/3492

Claims Analysis

Total Claims: 36
Claim 1
Independent Claim 501 words
A compound having one of the formulas I to VI wherein R₁ is hydrogen, halogen, alkyl of 1 to 12 carbon atoms or aralkyl of 7 to 15 carbon atoms, R and R₂ are independently hydrogen, alkyl of 1 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms or the group of formula VII with the proviso that one of R₂ and R is a group of formula VII R₃ and R₄ are independently alkyl of 1 to 4 carbon atoms or together R₃ and R₄ are pentamethylene, M is a direct bond, -NG₉-, -O-, -S-, -SO₂NG₉, -SO₂-, -SO₂O-, -CONG₉-, -COO- or -OCO-, L is a direct bond, alkylene of 1 to 12 carbon atoms, alkenylene of 3 to 18 carbon atoms, alkynylene of 3 to 18 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, said alkylene interrupted by one or more -O- atoms, X is -COO-, -CONG₉-, -O-, -NG₉- or -NY- where G₉ is hydrogen or alkyl of 1 to 8 carbon atoms, R₅ is hydrogen or hydroxyl, R₆ is -CO-, -CHOHCH₂- or -CH(CH₂OH)-, G₁, G₂, G₃, and G₄ are independently hydrogen, halogen, alkyl of 1 to 12 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 15 carbon atoms, phenoxy, alkoxy of 1 to 12 carbon atoms, -OCH₂COO-L₁ or the group T where L₁ is alkyl of 1 to 8 carbon atoms, and T is with the proviso that at least one of G₁ to G₄ must be T, G₅ and G₆ have independently the same definitions as G₁ to G₄, with the proviso that at least one of G₅ and G₆ do not need to be T, G₇ is hydrogen, phenyl or phenyl substituted by G₅, G₈ is cyano, -COO-L or -CO-X-Y, where E is hydrogen, 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, T₁, T₂ and T₃ are independently alkyl of 1 to 12 carbon atoms, aryl of 6 to 10 carbon atoms, said aryl substituted by one or two alkyl of 1 to 4 carbon atoms, aralkyl of 7 to 15 carbon atoms, -OR₇, -SR₇, -NR₇R₈, -SO₃H, or o-hydroxyphenyl substituted by the group T, with the proviso that at least one of T₁, T₂ and T₃ must be o-hydroxyphenyl substituted by the group T, and R₇ and R₈ are independently hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, alkoxyalkyl of 2 to 12 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 10 carbon atoms, said aryl substituted by one or two alkyl of 1 to 4 carbon atoms, aralkyl of 7 to 15 carbon atoms, or the group Y.
Claim 2
Dependent Claim 501 words
A compound having one of the formulas I to VI wherein R₁ is hydrogen, halogen, alkyl of 1 to 12 carbon atoms or aralkyl of 7 to 15 carbon atoms, R and R₂ are independently hydrogen, alkyl of 1 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms or the group of formula VII with the proviso that one of R₂ and R is a group of formula VII R₃ and R₄ are independently alkyl of 1 to 4 carbon atoms or together R₃ and R₄ are pentamethylene, M is a direct bond, -NG₉-, -O-, -S-, -SO₂NG₉, -SO₂-, -SO₂O-, -CONG₉-, -COO- or -OCO-, L is a direct bond, alkylene of 1 to 12 carbon atoms, alkenylene of 3 to 18 carbon atoms, alkynylene of 3 to 18 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, said alkylene interrupted by one or more -O- atoms, X is -COO-, -CONG₉-, -O-, -NG₉- or -NY- where G₉ is hydrogen or alkyl of 1 to 8 carbon atoms, R₅ is hydrogen or hydroxyl, R₆ is -CO-, -CHOHCH₂- or -CH(CH₂OH)-, G₁, G₂, G₃, and G₄ are independently hydrogen, halogen, alkyl of 1 to 12 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 15 carbon atoms, phenoxy, alkoxy of 1 to 12 carbon atoms, -OCH₂COO-L₁ or the group T where L₁ is alkyl of 1 to 8 carbon atoms, and T is with the proviso that at least one of G₁ to G₄ must be T, G₅ and G₆ have independently the same definitions as G₁ to G₄, with the proviso that at least one of G₅ and G₆ do not need to be T, G₇ is hydrogen, phenyl or phenyl substituted by G₅, G₈ is cyano, -COO-L or -CO-X-Y, where E is hydrogen, 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, T₁, T₂ and T₃ are independently alkyl of 1 to 12 carbon atoms, aryl of 6 to 10 carbon atoms, said aryl substituted by one or two alkyl of 1 to 4 carbon atoms, aralkyl of 7 to 15 carbon atoms, -OR₇, -SR₇, -NR₇R₈, -SO₃H, or o-hydroxyphenyl substituted by the group T, with the proviso that at least one of T₁, T₂ and T₃ must be o-hydroxyphenyl substituted by the group T, and R₇ and R₈ are independently hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, alkoxyalkyl of 2 to 12 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 10 carbon atoms, said aryl substituted by one or two alkyl of 1 to 4 carbon atoms, aralkyl of 7 to 15 carbon atoms, or the group Y.
Claim 3
Dependent Claim 23 words
A compound of formula I according to claim 1 wherein R₁ is hydrogen, chloro, alkyl of 1 to 4 carbon atoms or alpha,alpha-dimethylbenzyl.
Claim 4
Dependent Claim 12 words
A compound according to claim 2 wherein R₁ is hydrogen or chloro.
Claim 5
Dependent Claim 21 words
A compound of formula I according to claim 1 weherin R₂ is alkyl of 1 to 8 carbon atoms or alpha,alpha-­dimethylbenzyl.
Claim 6
Dependent Claim 14 words
A compound according to claim 4 wherein R₂ is methyl, tert-butyl, tert-amyl or tert-octyl.
Claim 7
Dependent Claim 13 words
A compound according to claim 1 wherein R₃ and R₄ are each methyl.
Claim 8
Dependent Claim 13 words
A compound of formula III according to claim 1 where R₅ is hydrogen.
Claim 9
Dependent Claim 13 words
A compound of formula III according to claim 1 where R₆ is -CO-.
Claim 10
Dependent Claim 16 words
A compound of formula IV according to claim 1 where G₁ and G₄ are each hydrogen.
Claim 11
Dependent Claim 13 words
A compound of formula V according to claim 1 where G₅ is hydrogen.
Claim 12
Dependent Claim 30 words
A compound of formula IV or V according to claim 1 where G₃ or G₆ is T, ethoxy or -OCH₂COO-L₁ where L₁ is alkyl of 2 to 8 carbon atoms.
Claim 13
Dependent Claim 14 words
A compound according to claim 11 wherein L₁ is ethyl, n-butyl, n-octyl or isooctyl.
Claim 14
Dependent Claim 13 words
A compound of formula VI according to claim 1 wherein G₇ is hydrogen.
Claim 15
Dependent Claim 13 words
A compound of formula VI according to claim 1 wherein G₈ is cyano.
Claim 16
Dependent Claim 12 words
A compound according to claim 1 wherein X is -O- or -NH-.
Claim 17
Dependent Claim 19 words
A compound according to claim 1 wherein E is alkyl of 1 to 12 carbon atoms, cyclohexyl or alpha-methyl­benzyl.
Claim 18
Dependent Claim 16 words
A compound according to claim 16 wherein E is methyl, heptyl, octyl, nonyl, cyclohexyl or alpha-methyl­benzyl.
Claim 19
Dependent Claim 30 words
A compound of formula I according to claim 1 wherein R is a group of formula VII where M is a direct bond, L is ethylene and X is -COO-.
Claim 20
Dependent Claim 10 words
The compound according to claim 1 which is 1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl 3-(2H-benzo­triazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate.
Claim 21
Dependent Claim 10 words
The compound according to claim 1 which is 1-­cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl 3(2H-benzo­triazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate.
Claim 22
Dependent Claim 10 words
The compound according to claim 1 which is 1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl 3-(2H-benzo­triazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate.
Claim 23
Dependent Claim 9 words
The compound according to claim 1 which is N-(1-­octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-3-(2H-benzo­triazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamamide.
Claim 24
Dependent Claim 14 words
The compound according to claim 1 which is 2-hydroxy-4-[(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-­yloxy)-carbonylmethoxy]benzophenone; 2-hydroxy-4-[N-(1-­methoxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-butylamino­carbonylmethoxy]benzophenone; 2-hydroxy-4-[3-(N-(1-cyclo­hexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)amino)-2-­hydroxypropoxy]benzophenone; 2-hydroxy-4-[3-(N-butyl-N-(1-­cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)amino)-2-­hydroxypropoxy]benzophenone; or 2-hydroxy-4-[3-(1-cyclo­hexyloxy-2,2,6,6-tetramethylpiperidin-4-yloxy)-2-hydroxy­propoxy]benzophenone.
Claim 25
Dependent Claim 11 words
The compound according to claim 1 which is 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-((1-octyloxy-­2,2,6,6-tetramethylpiperidin-4-yloxy)carbonylmethoxy)­phenyl]-s-triazine; or 2,4-bis(2,4-dimethylphenyl)-6-[2-­hydroxy-4-((1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-­yloxy)carbonylmethoxy)-phenyl]-s-triazine.
Claim 26
Dependent Claim 14 words
The compound according to claim 1 which is 2-ethoxy-2′-[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperi­ din-4-yl)aminocarbonylmethoxy]oxanilide; 2′-ethoxy-2-[(1-­cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yloxy)carbon­ylmethoxy]oxanilide; 2,2′-bis[(1-cyclohexyloxy-2,2,6,6-­tetramethylpiperidin-4-yloxy)carbonylmethoxy]oxanilide; or 2,2′-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-­yl)aminocarbonylmethoxy]oxanilide.
Claim 27
Dependent Claim 9 words
The compound according to claim 1 which is N-(2-octyloxycarbonylmethoxyphenyl)-N′-(1-octyloxy-2,2,6,6-­tetramethylpiperidin-4-yl)oxamide.
Claim 28
Dependent Claim 10 words
The compound according to claim 1 which is trans-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) alpha-cyanocinnamate.
Claim 29
Dependent Claim 14 words
The compound according to claim 1 which is ethyl 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl benzalmalonate; or bis(1-cyclohexyloxy-2,2,6,6-tetra­methylpiperidin-4-yl) benzalmalonate.
Claim 30
Dependent Claim 31 words
A stabilized composition which comprises (a) a polymer subject to degradation by the deleterious effects of actinic light, and (b) an effective stabilizing amount of a compound according to claim 1.
Claim 31
Dependent Claim 12 words
A composition according to claim 29 wherein the polymer is a polyolefin.
Claim 32
Dependent Claim 11 words
A composition according to claim 30 wherein the polyolefin is polypropylene.
Claim 33
Dependent Claim 12 words
A composition according to claim 29 wherein component (b) is 1-cyclohexyloxy-2,2,6,6-tetramethyl­piperdin-4-yl 3-(2H-benzotriazol-2-yl)-5-tert-butyl-­4-hydroxyhydrocinnamate.
Claim 34
Dependent Claim 27 words
A composition according to claim 29 wherein the polymer is a coating system based on alkyd, acrylic, acrylic alkyd, polyester, epoxide, urethane, polyamide vinyl or epoxy-polyester resins.
Claim 35
Dependent Claim 15 words
A composition according to claim 33 which contains a UV absorber or additional light stabilizer.
Claim 36
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.

References Cited (Backward Citations)

No citation records indexed.

USPTO Annuity & Maintenance Windows

Maintenance schedule is calculated for granted US utility patents.

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag