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US4308194A Expired / Lapsed US ⏱️ 0.0 years remaining

Heterocyclic benzoate ultraviolet stabilizers and their use in organic compositions

Assignee: Eastman Chemical Co
•
Filing: 1978-02-17
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Granted: 1981-12-29
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Expires: 1998-02-17
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Abstract

Abstract The invention relates to heterocyclic benzoate compounds which have been found to be effective ultraviolet stabilizers. The invention also relates to ultraviolet degradable organic compositions containing an amount of a heterocyclic benzoate composition to prevent such degradation. These stabilizers are effective in the presence of other additives commonly employed in polymeric compositions including, for example, pigments, colorants, fillers, reinforcing agents and the like. These ultraviolet stabilizers may be incorporated into the organic compositions such as polymers by adding to the polymer melt or dissolved in the polymer dope, coated on the exterior of the shaped or molded article, film or extruded fiber.

Inventors

  • 👤 Gether Irick, Jr.
  • 👤 Charles A. Kelly

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 14:46
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/10; C07D209/18; C07D235/00; C07D235/02; C07D235/04; C07D235/18; C07D249/00; C07D249/16; C07D249/18; C07D249/20; C07D277/00; C07D277/60; C07D277/62; C07D277/64; C07D277/66; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/35; C09; C09K; C09K15/00; C09K15/04; C09K15/06

Claims Analysis

Total Claims: 46
Claim 1
Independent Claim 399 words
An organic composition susceptible to ultraviolet light degradation stabilized against such degradation with a stabilizing amount of at least one ester of a heterocyclic aromatic acid compound having the following formula: ##STR15## wherein A is a group having the structure ##STR16## wherein X and Y are a carbon atom or a nitrogen atom; Z is an oxygen atom, a sulfur atom, a nitrogen atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; R 1 , R 2 , R 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, lower alkylaryl, aryl-substituted-aryl, alkoxy, substituted amino, cyano, and the substituents R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 , combined with the carbon atoms to which they are attached are joined alkylene groups completing a carbocyclic ring, which ring can also be substituted with one or more of the substituents listed above for R 1 , R 2 , R 3 and R 4 ; I is the same as R 1 , R 2 , R 3 and R 4 and is present on all positions of the benzenoid ring, except the carbon atom attached to the Y substituent and the carbon atom attached to the carboxyl group connecting the heterocyclic aromatic A group with the aromatic B group, said carbonyl connecting group is attached to the benzenoid ring in either the meta or para position from the carbon atom connected to the Y substituent; and B is a group having the formula: ##STR17## wherein: at least one R 5 or R 9 is hydrogen and the other R 5 , R 6 , R 7 , R 8 and R 9 are hydrogen, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, lower alkylaryl, aryl-substituted-aryl, alkoxy, substituted amino, carboalkoxy, nitrile, chloro, bromo and the substituents R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 combined with the carbon atoms to which they are attached are joined alkylene groups completing a carbocyclic ring which can be substituted with any of the substituents listed above for R 5 , R 6 , R 7 , R 8 and R 9 .
Claim 2
Dependent Claim 399 words
An organic composition susceptible to ultraviolet light degradation stabilized against such degradation with a stabilizing amount of at least one ester of a heterocyclic aromatic acid compound having the following formula: ##STR15## wherein A is a group having the structure ##STR16## wherein X and Y are a carbon atom or a nitrogen atom; Z is an oxygen atom, a sulfur atom, a nitrogen atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; R 1 , R 2 , R 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, lower alkylaryl, aryl-substituted-aryl, alkoxy, substituted amino, cyano, and the substituents R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 , combined with the carbon atoms to which they are attached are joined alkylene groups completing a carbocyclic ring, which ring can also be substituted with one or more of the substituents listed above for R 1 , R 2 , R 3 and R 4 ; I is the same as R 1 , R 2 , R 3 and R 4 and is present on all positions of the benzenoid ring, except the carbon atom attached to the Y substituent and the carbon atom attached to the carboxyl group connecting the heterocyclic aromatic A group with the aromatic B group, said carbonyl connecting group is attached to the benzenoid ring in either the meta or para position from the carbon atom connected to the Y substituent; and B is a group having the formula: ##STR17## wherein: at least one R 5 or R 9 is hydrogen and the other R 5 , R 6 , R 7 , R 8 and R 9 are hydrogen, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, lower alkylaryl, aryl-substituted-aryl, alkoxy, substituted amino, carboalkoxy, nitrile, chloro, bromo and the substituents R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 combined with the carbon atoms to which they are attached are joined alkylene groups completing a carbocyclic ring which can be substituted with any of the substituents listed above for R 5 , R 6 , R 7 , R 8 and R 9 .
Claim 3
Dependent Claim 13 words
An organic composition according to claim 1 wherein X is a carbon atom.
Claim 4
Dependent Claim 13 words
An organic composition according to claim 1 wherein X is a nitrogen atom.
Claim 5
Dependent Claim 13 words
An organic composition according to claim 2 wherein Y is a carbon atom.
Claim 6
Dependent Claim 13 words
An organic composition according to claim 2 wherein Y is a nitrogen atom.
Claim 7
Dependent Claim 13 words
An organic composition according to claim 3 wherein Y is a carbon atom.
Claim 8
Dependent Claim 13 words
An organic composition according to claim 6 wherein Z is a sulfur atom.
Claim 9
Dependent Claim 13 words
An organic composition according to claim 6 wherein Z is a nitrogen atom.
Claim 10
Dependent Claim 25 words
An organic composition according to claim 6 wherein Z is a nitrogen atom containing hydrogen or an alkyl group having 1 to 12 carbon atoms.
Claim 11
Dependent Claim 13 words
An organic composition according to claim 6 wherein Z is an oxygen atom.
Claim 12
Dependent Claim 70 words
An organic composition according to claim 10 susceptible to ultraviolet light degradation stabilized against such degradation with a stabilizing amount of at least one compound having the formula: ##STR18## wherein R 2 is hydrogen, alkyl, alkylaryl or nitrile; R 3 is hydrogen or alkyl, and R 5 , R 6 , R 7 , R 8 , and R 9 are hydrogen, alkyl, alkoxy, halogen, cycloalkyl, nitrile, aryl, or alkyl-substituted-cycloalkyl.
Claim 13
Dependent Claim 55 words
An organic composition according to claim 11 wherein said stabilizing compound has the formula: ##STR19## wherein R 2 is hydrogen, alkyl, alkylaryl or nitrile; R 3 is hydrogen or alkyl; and R 5 , R 6 , R 7 , R 8 and R 9 are hydrogen, alkyl, alkoxy, halogen, cycloalkyl, nitrile, aryl, or alkyl-substituted-cycloalkyl.
Claim 14
Dependent Claim 56 words
An organic composition according to claim 11 wherein said stabilizing compound has the formula: ##STR20## wherein R 2 is hydrogen, alkyl, alkylaryl or nitrile; R 3 is hydrogen or alkyl; and R 5 , R 6 , R 7 , R 8 , and R 9 are hydrogen, alkyl, alkoxy, halogen, cycloalkyl, nitrile, aryl or alkyl-substituted-cycloalkyl.
Claim 15
Dependent Claim 31 words
An organic composition according to claim 12 wherein said stabilizing compound has the formula: ##STR21## wherein R 2 is hydrogen, alkyl, alkylaryl or nitrile; and R 3 is hydrogen or alkyl.
Claim 16
Dependent Claim 39 words
An organic composition according to claim 12 wherein said stabilizing compound has the formula: ##STR22## where R 2 is hydrogen, alkyl, alkylaryl or nitrile; R 3 is hydrogen or alkyl; and R 6 is lower alkyl or lower alkoxy.
Claim 17
Dependent Claim 35 words
An organic composition according to claim 15 wherein said stabilizing compound has the formula: ##STR23## wherein R 2 and R 3 are hydrogen or lower alkyl and R 6 is lower alkyl or lower alkoxy.
Claim 18
Dependent Claim 38 words
An organic composition according to claim 16 wherein said stabilizing compound has the formula: ##STR24## wherein R 2 and R 3 are hydrogen or lower alkyl and R 6 is lower alkyl containing 1 to 18 carbon atoms.
Claim 19
Dependent Claim 11 words
An organic composition according to claim 17 having the formula: ##STR25##
Claim 20
Dependent Claim 15 words
An organic composition according to claim 16 wherein said stabilizing compound has the formula: ##STR26##
Claim 21
Dependent Claim 15 words
An organic composition according to claim 12 wherein said stabilizing compound has the formula: ##STR27##
Claim 22
Dependent Claim 15 words
An organic composition according to claim 12 wherein said stabilizing compound has the formula: ##STR28##
Claim 23
Dependent Claim 15 words
An organic composition according to claim 12 wherein said stabilizing compound has the formula: ##STR29##
Claim 24
Dependent Claim 15 words
An organic composition according to claim 13 wherein said stabilizing compound has the formula: ##STR30##
Claim 25
Dependent Claim 15 words
An organic composition according to claim 13 wherein said stabilizing compound has the formula: ##STR31##
Claim 26
Dependent Claim 15 words
An organic composition according to claim 13 wherein said stabilizing compound has the formula: ##STR32##
Claim 27
Dependent Claim 15 words
An organic composition according to claim 13 wherein said stabilizing compound has the formula: ##STR33##
Claim 28
Dependent Claim 13 words
An organic composition according to claim 5 wherein Z is a sulfur atom.
Claim 29
Dependent Claim 13 words
An organic composition according to claim 5 wherein Z is an oxygen atom.
Claim 30
Dependent Claim 29 words
An organic composition according to claim 5 wherein Z is a nitrogen atom containing hydrogen or a substituted or unsubstituted lower alkyl group containing 1 to 12 carbon atoms.
Claim 31
Dependent Claim 13 words
An organic composition according to claim 5 wherein Z is a nitrogen atom.
Claim 32
Dependent Claim 52 words
An organic composition according to claim 30 comprising compounds having the formula: ##STR34## wherein R 2 is hydrogen, alkyl, alkylaryl, or nitrile; R 3 is hydrogen or alkyl; and R 5 , R 6 , R 7 , R 8 and R 9 are hydrogen, alkyl, alkoxy, halogen, cycloalkyl, nitrile, aryl, di-alkyl-substituted-cycloalkyl.
Claim 33
Dependent Claim 51 words
An organic composition according to claim 31 having the formula: ##STR35## wherein R 2 is hydrogen, alkyl, alkylaryl or nitrile; R 3 is hydrogen or alkyl; and R 5 , R 6 , R 7 , R 8 and R 9 are hydrogen, alkyl, alkoxy, halogen, cycloalkyl, nitrile, aryl, or alkyl-substituted-cycloalkyl.
Claim 34
Dependent Claim 51 words
An organic composition according to claim 31 having the formula: ##STR36## wherein R 2 is hydrogen, alkyl, alkylaryl or nitrile; R 3 is hydrogen or alkyl; and R 5 , R 6 , R 7 , R 8 and R 9 are hydrogen, alkyl, alkoxy, halogen, cycloalkyl, nitirle, aryl, or alkyl-substituted-cycloalkyl.
Claim 35
Dependent Claim 39 words
An organic composition according to claim 32 wherein said stabilizing compound has the formula: ##STR37## wherein R 2 is hydrogen, alkyl, alkylaryl or nitrile; R 3 is hydrogen or alkyl; and R 6 is lower alkyl or lower alkoxy.
Claim 36
Dependent Claim 35 words
An organic composition according to claim 34 wherein said stabilizing compound has the formula: ##STR38## wherein R 2 and R 3 are hydrogen or lower alkyl and R 6 is lower alkyl or lower alkoxy.
Claim 37
Dependent Claim 38 words
An organic composition according to claim 35 wherein said stabilizing compound has the formula: ##STR39## wherein R 2 and R 3 are hydrogen or lower alkyl and R 6 is lower alkyl containing 1 to 18 carbon atoms.
Claim 38
Dependent Claim 11 words
An organic composition according to claim 36 having the formula: ##STR40##
Claim 39
Dependent Claim 11 words
An organic composition according to claim 35 having the formula: ##STR41##
Claim 40
Dependent Claim 11 words
An organic composition according to claim 32 having the formula: ##STR42##
Claim 41
Dependent Claim 11 words
An organic composition according to claim 32 having the formula: ##STR43##
Claim 42
Dependent Claim 11 words
An organic composition according to claim 32 having the formula: ##STR44##
Claim 43
Dependent Claim 11 words
An organic composition according to claim 33 having the formula: ##STR45##
Claim 44
Dependent Claim 11 words
An organic composition according to claim 33 having the formula: ##STR46##
Claim 45
Dependent Claim 11 words
An organic composition according to claim 33 having the formula: ##STR47##
Claim 46
Dependent Claim 11 words
An organic composition according to claim 33 having the formula: ##STR48##

References Cited (Backward Citations)

US2737516A Cited
US2995540A Cited
US3112338A Cited
US3519599A Cited
US3551443A Cited
US3886117A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-12-28 1985-06-29 1985-12-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-12-28 1989-06-29 1989-12-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-12-28 1993-06-29 1993-12-29 $7700.00 Window Closed / Lapsed

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