US4162254A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Benzoxazole ultraviolet stabilizers
Assignee: Eastman Chemical Co
•
Filing: 1977-10-12
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Granted: 1979-07-24
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Expires: 1997-10-12
Abstract
Abstract The invention relates to aryl ester-based compounds which have been found to be extremely effective ultraviolet stabilizers. The invention also relates to ultraviolet degradable organic compositions containing an amount of an aryl ester-based 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 in the polymer melt or dissolved in the polymer dope, or 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
2026-11-08 05:16
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/35; C08K5/36; C08K5/45; C08K5/46
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
318 words
A composition of matter having the formula ##STR33## wherein A is a member having the formula: ##STR34## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, cyclohexyl, phenyl, lower alkylphenyl, phenyl-substituted-phenyl, alkoxy, 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 atoms attached to the heterocyclic substituent and the carbon atom attached to the E group, said E group is attached to the benzenoid ring in either the meta or para position from the carbon atom connected to the heterocyclic substituent; and E is a member selected from the group consisting of, lower alkyloxy, oxy-lower alkyl and oxy; B is a group having the formula ##STR35## 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, cyclohexyl, phenyl, lower alkylphenyl, phenyl-substituted-phenyl, alkoxy, hydroxy, carboalkoxy, nitrile, chloro, bromo and the substituents R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , and 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
318 words
A composition of matter having the formula ##STR33## wherein A is a member having the formula: ##STR34## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, cyclohexyl, phenyl, lower alkylphenyl, phenyl-substituted-phenyl, alkoxy, 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 atoms attached to the heterocyclic substituent and the carbon atom attached to the E group, said E group is attached to the benzenoid ring in either the meta or para position from the carbon atom connected to the heterocyclic substituent; and E is a member selected from the group consisting of, lower alkyloxy, oxy-lower alkyl and oxy; B is a group having the formula ##STR35## 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, cyclohexyl, phenyl, lower alkylphenyl, phenyl-substituted-phenyl, alkoxy, hydroxy, carboalkoxy, nitrile, chloro, bromo and the substituents R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , and 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
176 words
A composition of matter according to claim 1 wherein A has the structure ##STR36## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, cyclohexyl, phenyl, lower alkylphenyl, phenyl-substituted-phenyl, alkoxy, 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 ; and 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 heterocyclic substituent and the carbon atom attached to the oxymethylene group, said oxymethylene group is attached to the benzenoid ring in either the meta or para position from the carbon atom connected to the heterocyclic substituent.
Claim 4
Dependent Claim
274 words
A composition of matter according to claim 2 having the structure ##STR37## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, cyclohexyl, phenyl, lower alkylphenyl, phenyl-substituted-phenyl, alkoxy, 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 ; and 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 heterocyclic substituent and the carbon atom attached to the oxymethylene group and the carbon atom attached to the carbonyl connecting group; and 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, cyclohexyl, phenyl, lower alkylphenyl, phenyl-substitued-phenyl, alkoxy, hydroxy, carboalkoxy, nitrile, chloro, bromo and the substituents R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , and 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 5
Dependent Claim
12 words
A composition of matter according to claim 2 having the structure ##STR38##
Claim 6
Dependent Claim
12 words
A composition of matter according to claim 3 having the structure ##STR39##
Claim 7
Dependent Claim
12 words
A composition of matter according to claim 3 having the structure ##STR40##
Claim 8
Dependent Claim
12 words
A composition of matter according to claim 3 having the structure ##STR41##
Claim 9
Dependent Claim
12 words
A composition of matter according to claim 3 having the structure ##STR42##
Claim 10
Dependent Claim
12 words
A composition of matter according to claim 3 having the structure ##STR43##
Claim 11
Dependent Claim
12 words
A composition of matter according to claim 3 having the structure ##STR44##
Claim 12
Dependent Claim
177 words
A composition of matter according to claim 1 wherein A has the structure ##STR45## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, alkoxy, 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 ; and 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 heterocyclic substituent and the carbon atom attached to the methyleneoxy group, said methyleneoxy group is attached to the benzenoid ring in either the meta or para position from the carbon atom connected to the heterocyclic substituent.
Claim 13
Dependent Claim
270 words
A composition of matter according to claim 11 having the structure ##STR46## wherein R 1 , r 2 , r 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, alkoxy, 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 heterocyclic substituent and the carbon atom attached to the methyleneoxy group and the carbonyl connecting group; and 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, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, alkoxy, hydroxy, carboalkoxy, nitrile, chloro, bromo and the substituents R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , and 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 14
Dependent Claim
12 words
A composition of matter according to claim 12 having the structure ##STR47##
Claim 15
Dependent Claim
12 words
A composition of matter according to claim 12 having the structure ##STR48##
Claim 16
Dependent Claim
12 words
A composition of matter according to claim 12 having the structure ##STR49##
Claim 17
Dependent Claim
12 words
A composition of matter according to claim 12 having the structure ##STR50##
Claim 18
Dependent Claim
12 words
A composition of matter according to claim 12 having the structure ##STR51##
Claim 19
Dependent Claim
12 words
A composition of matter according to claim 12 having the structure ##STR52##
Claim 20
Dependent Claim
12 words
A composition of matter according to claim 12 having the structure ##STR53##
Claim 21
Dependent Claim
295 words
A composition of matter according to claim 1 having the structure ##STR54## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, alkoxy, 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 heterocyclic substituent and the carbon atom attached to the oxy group and the carbonyl connecting group, said oxy connecting group is attached to the benzenoid ring in either the meta or para position from the carbon atom connected to the heterocyclic substituent; and 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, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, alkoxy, hydroxy, carboalkoxy, nitrile, chloro, bromo and the substituents R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , and 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 for R 5 , R 6 , R 7 , R 8 and R 9 .
Claim 22
Dependent Claim
269 words
A composition of matter according to claim 20 having the structure ##STR55## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, chloro, bromo, lower alkyl, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, alkoxy, 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 heterocyclic substituent and the carbon atom attached to the oxy group and the carbonyl connecting group; 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, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, alkoxy, hydroxy, carboalkoxy, nitrile, chloro, bromo and the substituents R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , and 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 23
Dependent Claim
12 words
A composition of matter according to claim 21 having the structure ##STR56##
Claim 24
Dependent Claim
12 words
A composition of matter according to claim 21 having the structure ##STR57##
Claim 25
Dependent Claim
12 words
A composition of matter according to claim 21 having the structure ##STR58##
Claim 26
Dependent Claim
12 words
A composition of matter according to claim 21 having the structure ##STR59##
Claim 27
Dependent Claim
12 words
A composition of matter according to claim 21 having the structure ##STR60##
Claim 28
Dependent Claim
12 words
A composition of matter according to claim 21 having the structure ##STR61##
Claim 29
Dependent Claim
12 words
A composition of matter according to claim 21 having the structure ##STR62##
References Cited (Backward Citations)
US3864354A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-07-23 | 1983-01-22 | 1983-07-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-07-23 | 1987-01-22 | 1987-07-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-07-23 | 1991-01-22 | 1991-07-24 | $7700.00 | Window Closed / Lapsed |