← Back to Patent Explorer
US4247692A Expired / Lapsed US ⏱️ 0.0 years remaining

Triazine derivatives

Assignee: Akzona Inc
•
Filing: 1978-06-19
•
Granted: 1981-01-27
•
Expires: 1998-06-19
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Novel triazine derivatives which are with cyanoacetic acid, derivatives of cyanoacetic acid or malodinitrile substituted s-triazines and which provide stabilizers against ultraviolet radiation for organic polymers such as polyvinyl chloride or copolymers of polyvinyl chloride or polypropylene are obtained by reacting the corresponding chloro-s-triazinyl derivatives with sodium hydride or a metal lower alcoholate in an organic solvent, and isolating the resulting product by acidification.

Inventors

  • 👤 Hermannus J. M. Sinnige
  • 👤 Hendrik J. Hageman
  • 👤 Willem J. Mijs
  • 👤 Stephanus A. G. de Graaf
  • 👤 Vincent Oakes

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 03:03
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477; C08K5/3492; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/14; C07D251/16; C07D251/18; C07D251/20; C07D251/22; C07D251/24; C07D251/26; C07D251/38

Claims Analysis

Total Claims: 56
Claim 1
Independent Claim 519 words
A compound of the formula: ##STR10## wherein m, n, p, and q are independently 0 or 1, provided that n=0 if m=0 and q=0 if p=0; when m=0, X is selected from the group consisting of chlorine, ZH, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when m=1 and n=0, X is selected from the group consisting of alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when m=1 and n=1, X is selected from the group consisting of hydrogen, alkanoyl having 2 to 20 carbon atoms, benzoyl, benzene sulphonyl, amino, monoalkylamine having 2 to 8 carbon atoms, dialkylamino having 2 to 8 carbon atoms, phenylamino, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when p=0, Y is selected from the group consisting of ZH, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when p=1 and q=0, Y is selected from the group consisting of alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when p=1 and q=1, Y is selected from the group consisting of hydrogen, alkanoyl having 2 to 20 carbon atoms, benzoyl, benzene sulphonyl, amino, monoalkylamino having 2 to 8 carbon atoms, dialkylamino having 2 to 8 carbon atoms, phenylamino, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when m=1 and n=1, A is nitrogen; when p=1 and q=1, B is nitrogen; when m=1 and n=0, A is oxygen or sulfur; when p=1 and q=0, B is oxygen or sulfur; when p=1 and q=1, C is selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when n=1 and m=1, D is selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; the groups Y, B, and C being capable of forming a heterocyclic ring having 2 to 5 carbon atoms in which B represents the hetero nitrogen atom; the groups X, A, and D being capable of forming a heterocyclic ring having 2 to 5 carbon atoms in which A represents the hetero nitrogen atom; in all instances ZH represents a group which may lose a hydrogen atom in favor of an adjacent nitrogen atom of the triazine ring to form a desmotropic structure of the formula: ##STR11## Z is in all instances a group of the formula ##STR12## in which R 1 is selected from the group consisting of CN, ##STR13## wherein R 2 is selected from the group consisting of hydrogen, alkyl, aralkyl, and cycloalkyl.
Claim 2
Dependent Claim 519 words
A compound of the formula: ##STR10## wherein m, n, p, and q are independently 0 or 1, provided that n=0 if m=0 and q=0 if p=0; when m=0, X is selected from the group consisting of chlorine, ZH, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when m=1 and n=0, X is selected from the group consisting of alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when m=1 and n=1, X is selected from the group consisting of hydrogen, alkanoyl having 2 to 20 carbon atoms, benzoyl, benzene sulphonyl, amino, monoalkylamine having 2 to 8 carbon atoms, dialkylamino having 2 to 8 carbon atoms, phenylamino, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when p=0, Y is selected from the group consisting of ZH, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when p=1 and q=0, Y is selected from the group consisting of alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when p=1 and q=1, Y is selected from the group consisting of hydrogen, alkanoyl having 2 to 20 carbon atoms, benzoyl, benzene sulphonyl, amino, monoalkylamino having 2 to 8 carbon atoms, dialkylamino having 2 to 8 carbon atoms, phenylamino, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when m=1 and n=1, A is nitrogen; when p=1 and q=1, B is nitrogen; when m=1 and n=0, A is oxygen or sulfur; when p=1 and q=0, B is oxygen or sulfur; when p=1 and q=1, C is selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; when n=1 and m=1, D is selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, and phenyl; the groups Y, B, and C being capable of forming a heterocyclic ring having 2 to 5 carbon atoms in which B represents the hetero nitrogen atom; the groups X, A, and D being capable of forming a heterocyclic ring having 2 to 5 carbon atoms in which A represents the hetero nitrogen atom; in all instances ZH represents a group which may lose a hydrogen atom in favor of an adjacent nitrogen atom of the triazine ring to form a desmotropic structure of the formula: ##STR11## Z is in all instances a group of the formula ##STR12## in which R 1 is selected from the group consisting of CN, ##STR13## wherein R 2 is selected from the group consisting of hydrogen, alkyl, aralkyl, and cycloalkyl.
Claim 3
Dependent Claim 2 words
(2,4-diallyl-s-triazinyl-6-)methyl cyanoacetate.
Claim 4
Dependent Claim 2 words
(2,4-diallyl-s-triazinyl-6-)methyl cyanoacetate.
Claim 5
Dependent Claim 2 words
(2,4-dimethoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 6
Dependent Claim 2 words
(2,4-dimethoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 7
Dependent Claim 2 words
(2,4-dioctoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 8
Dependent Claim 2 words
(2,4-dioctoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 9
Dependent Claim 2 words
(2,4-dilauroxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 10
Dependent Claim 2 words
(2,4-dilauroxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 11
Dependent Claim 2 words
(2,4-distearoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 12
Dependent Claim 2 words
(2,4-distearoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 13
Dependent Claim 2 words
(2,4-dimethoxy-s-triazinyl-6-)lauryl cyanoacetate.
Claim 14
Dependent Claim 2 words
(2,4-dimethoxy-s-triazinyl-6-)lauryl cyanoacetate.
Claim 15
Dependent Claim 2 words
(2,4-dimethoxy-s-triazinyl-6-)benzyl cyanoacetate.
Claim 16
Dependent Claim 2 words
(2,4-dimethoxy-s-triazinyl-6-)benzyl cyanoacetate.
Claim 17
Dependent Claim 2 words
(2,4-dioctoxy-s-triazinyl-6-)benzyl cyanoacetate.
Claim 18
Dependent Claim 2 words
(2,4-dioctoxy-s-triazinyl-6-)benzyl cyanoacetate.
Claim 19
Dependent Claim 2 words
(2,4-dimethylthio-s-triazinyl-6-)methyl cyanoacetate.
Claim 20
Dependent Claim 2 words
(2,4-dimethylthio-s-triazinyl-6-)methyl cyanoacetate.
Claim 21
Dependent Claim 2 words
(2,4-diphenoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 22
Dependent Claim 2 words
(2,4-diphenoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 23
Dependent Claim 2 words
(2,4-bis[4-methoxyphenoxy-]-s-triazinyl-6-)methyl cyanoacetate.
Claim 24
Dependent Claim 2 words
(2,4-bis[4-methoxyphenoxy-]-s-triazinyl-6-)methyl cyanoacetate.
Claim 25
Dependent Claim 2 words
(2,4-diphenyl-s-triazinyl-6-)methyl cyanoacetate.
Claim 26
Dependent Claim 2 words
(2,4-diphenyl-s-triazinyl-6-)methyl cyanoacetate.
Claim 27
Dependent Claim 1 words
(2,4-dimethoxy-s-triazinyl-6-)malodinitrile.
Claim 28
Dependent Claim 1 words
(2,4-dimethoxy-s-triazinyl-6-)malodinitrile.
Claim 29
Dependent Claim 1 words
(2,4-dioctoxy-s-triazinyl-6-)malodinitrile.
Claim 30
Dependent Claim 1 words
(2,4-dioctoxy-s-triazinyl-6-)malodinitrile.
Claim 31
Dependent Claim 1 words
(2,4-dilauroxy-s-triazinyl-6-)malodinitrile.
Claim 32
Dependent Claim 1 words
(2,4-dilauroxy-s-triazinyl-6-)malodinitrile.
Claim 33
Dependent Claim 1 words
(2,4-distearoxy-s-triazinyl-6-)malodinitrile.
Claim 34
Dependent Claim 1 words
(2,4-distearoxy-s-triazinyl-6-)malodinitrile.
Claim 35
Dependent Claim 1 words
(2,4-dimethylthio-s-triazinyl-6-)malodinitrile.
Claim 36
Dependent Claim 1 words
(2,4-dimethylthio-s-triazinyl-6-)malodinitrile.
Claim 37
Dependent Claim 1 words
(2,4-diphenoxy-s-triazinyl-6-)malodinitrile.
Claim 38
Dependent Claim 1 words
(2,4-diphenoxy-s-triazinyl-6-)malodinitrile.
Claim 39
Dependent Claim 1 words
(2,4-di-(carbomethoxycyanomethyl)-6-methoxy-s-triazine.
Claim 40
Dependent Claim 1 words
(2,4-di-(carbomethoxycyanomethyl)-6-methoxy-s-triazine.
Claim 41
Dependent Claim 2 words
(2,4-dimethoxy-s-triazinyl-6-)phenyl cyanoacetate.
Claim 42
Dependent Claim 2 words
(2,4-dimethoxy-s-triazinyl-6-)phenyl cyanoacetate.
Claim 43
Dependent Claim 2 words
(2-diethylamino-4-phenoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 44
Dependent Claim 2 words
(2-diethylamino-4-phenoxy-s-triazinyl-6-)methyl cyanoacetate.
Claim 45
Dependent Claim 2 words
(2,4-dipiperidino-s-triazinyl-6-)methyl cyanoacetate.
Claim 46
Dependent Claim 2 words
(2,4-dipiperidino-s-triazinyl-6-)methyl cyanoacetate.
Claim 47
Dependent Claim 2 words
(2,4-dihydrazino-s-triazinyl-6-)methyl cyanoacetate.
Claim 48
Dependent Claim 2 words
(2,4-dihydrazino-s-triazinyl-6-)methyl cyanoacetate.
Claim 49
Dependent Claim 2 words
(2,4-bis[2-carbomethoxyethylmercapto]-s-triazinyl-6-)methyl cyanoacetate.
Claim 50
Dependent Claim 2 words
(2,4-bis[2-carbomethoxyethylmercapto]-s-triazinyl-6-)methyl cyanoacetate.
Claim 51
Dependent Claim 3 words
(2,4-bis[2 carbolauroxyethylmercapto]-s-triazinyl-6-)methyl cyanoacetate.
Claim 52
Dependent Claim 3 words
(2,4-bis[2 carbolauroxyethylmercapto]-s-triazinyl-6-)methyl cyanoacetate.
Claim 53
Dependent Claim 1 words
(2,4-dimethoxy-s-triazinyl-6-)cyanoacetamide.
Claim 54
Dependent Claim 1 words
(2,4-dimethoxy-s-triazinyl-6-)cyanoacetamide.
Claim 55
Dependent Claim 2 words
(2,4-bis(2-hydroxyethylamino)-s-triazinyl-6-)methyl cyanoacetate.
Claim 56
Dependent Claim 2 words
(2,4-bis(2-hydroxyethylamino)-s-triazinyl-6-)methyl cyanoacetate.

References Cited (Backward Citations)

US2394526A Cited
GB954992A Cited
US3700671A Cited
US4124763A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-01-27 1984-07-28 1985-01-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-01-27 1988-07-28 1989-01-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-01-27 1992-07-28 1993-01-27 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag