US4164480A
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US
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Polychromophoric ultraviolet stabilizers and their use in organic compositions
Assignee: Eastman Chemical Co
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Filing: 1978-01-09
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Granted: 1979-08-14
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Expires: 1998-01-09
Abstract
Abstract The invention relates to polychromophoric compounds which have been found to be effective ultraviolet stabilizers. The invention also relates to ultraviolet degradable organic compositions containing a stabilizing amount of the polychromophoric 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 also be incorporated into the organic compositions in the polymer melt or dissolved in the polymer dope, or coated on the exterior of the molded article, film or extruded fiber.
Inventors
- 👤 Gether Irick, Jr.
- 👤 James C. Ownby
- 👤 Richard H. S. Wang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 01:01
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/0008; C08K5/005; Y; Y10; Y10S; Y10S524/00; Y10S524/925; Y10S524/929
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
263 words
A polychromophoric compound having the formula: ##STR13## wherein A is a group having the structure: ##STR14## wherein R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; B is a heterocyclic group having the structures ##STR15## wherein X and Y are a carbon atom or a nitrogen atom or a carbon atom containing an alkyl group containing 1 to 12 carbon atoms or a carbon atom containing an aryl group containing 6 to 10 carbon atoms; Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, lower alkylaryl, aryl-substituted-aryl, alkoxy, aryloxy, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group, E is a substituted or unsubstituted branched or unbranched alkylene group containing 1 to 12 carbon atoms or arylene group containing 6 to 18 carbon atoms and n is 1 or 2.
Claim 2
Dependent Claim
263 words
A polychromophoric compound having the formula: ##STR13## wherein A is a group having the structure: ##STR14## wherein R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; B is a heterocyclic group having the structures ##STR15## wherein X and Y are a carbon atom or a nitrogen atom or a carbon atom containing an alkyl group containing 1 to 12 carbon atoms or a carbon atom containing an aryl group containing 6 to 10 carbon atoms; Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, lower alkylaryl, aryl-substituted-aryl, alkoxy, aryloxy, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group, E is a substituted or unsubstituted branched or unbranched alkylene group containing 1 to 12 carbon atoms or arylene group containing 6 to 18 carbon atoms and n is 1 or 2.
Claim 3
Dependent Claim
181 words
Polychromophoric compounds according to claim 1 having the formula ##STR16## R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group, E is a substituted or unsubstituted alkylene or arylene and n is 2.
Claim 4
Dependent Claim
205 words
Polychromophoric compounds according to claim 1 having the formula ##STR17## R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 to 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; J is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group; E is a substituted or unsubstituted alkylene or arylene and n is 2.
Claim 5
Dependent Claim
114 words
Polychromophoric compounds according to claim 1 having the formula ##STR18## R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; J is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms;
Claim 6
Dependent Claim
78 words
Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group.
Claim 7
Dependent Claim
78 words
Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group.
Claim 8
Dependent Claim
11 words
A polychromophoric compound according to claim 1 having the formula ##STR19##
Claim 9
Dependent Claim
11 words
A polychromophoric compound according to claim 2 having the formula ##STR20##
Claim 10
Dependent Claim
11 words
A polychromophoric compound according to claim 2 having the formula ##STR21##
Claim 11
Dependent Claim
11 words
A polychromophoric compound according to claim 1 having the formula ##STR22##
Claim 12
Dependent Claim
11 words
A polychromophoric compound according to claim 1 having the formula ##STR23##
Claim 13
Dependent Claim
11 words
A polychromophoric compound according to claim 4 having the formula ##STR24##
Claim 14
Dependent Claim
11 words
A polychromophoric compound according to claim 4 having the formula ##STR25##
Claim 15
Dependent Claim
11 words
A polychromophoric compound according to claim 4 having the formula ##STR26##
Claim 16
Dependent Claim
275 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of compounds having the formula: ##STR27## wherein A is a group having the structure ##STR28## wherein R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; B is a heterocyclic group having the structures ##STR29## wherein X and Y are a carbon atom, a carbon atom containing an alkyl group having 1 to 12 carbon atoms, a carbon atom containing an aryl group having 6 to 10 carbon atoms or a nitrogen atom; Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, lower alkylaryl, aryl-substituted-aryl, alkoxy, aryloxy, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group, E is a substituted or unsubstituted branched or unbranched alkylene group containing 1 to 12 carbon atoms or arylene group containing 6 to 18 carbon atoms and n is 1 or 2.
Claim 17
Dependent Claim
275 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of compounds having the formula: ##STR27## wherein A is a group having the structure ##STR28## wherein R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; B is a heterocyclic group having the structures ##STR29## wherein X and Y are a carbon atom, a carbon atom containing an alkyl group having 1 to 12 carbon atoms, a carbon atom containing an aryl group having 6 to 10 carbon atoms or a nitrogen atom; Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, lower alkylaryl, aryl-substituted-aryl, alkoxy, aryloxy, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group, E is a substituted or unsubstituted branched or unbranched alkylene group containing 1 to 12 carbon atoms or arylene group containing 6 to 18 carbon atoms and n is 1 or 2.
Claim 18
Dependent Claim
196 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of compounds according to claim 13 having the formula ##STR30## R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group; E is a substituted or unsubstituted alkylene or arylene and n is 2.
Claim 19
Dependent Claim
220 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of compounds according to claim 13 having the formula ##STR31## R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms. β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; J is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group; E is a substituted or unsubstituted alkylene or arylene and n is 2.
Claim 20
Dependent Claim
207 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of compounds according to claim 13 having the formula ##STR32## R 1 and R 2 and R 3 and R 4 are each alkyl having 1-6 carbons; R 1 and R 2 and R 3 and R 4 , together with the carbon to which they are bound, form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 5 is hydrogen, oxyl, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or alkyl substituted benzyl; J is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; Z is an oxygen atom, a sulfur atom, or a nitrogen atom containing a hydrogen atom or a substituted or unsubstituted lower alkyl group having 1 to 12 carbon atoms; I is hydrogen, chloro, bromo, fluoro, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted amino or cyano, said I being present on all positions of the benzenoid rings, except the carbon atom attached to the heterocyclic ring and the carbon atom attached to the carbonyloxy group.
Claim 21
Dependent Claim
18 words
An organic composition according to claim 14 containing a stabilizing amount of a compound having the formula ##STR33##
Claim 22
Dependent Claim
18 words
An organic composition according to claim 14 containing a stabilizing amount of a compound having the formula ##STR34##
Claim 23
Dependent Claim
18 words
An organic composition according to claim 14 containing a stabilizing amount of a compound having the formula ##STR35##
Claim 24
Dependent Claim
18 words
An organic composition according to claim 13 containing a stabilizing amount of a compound having the formula ##STR36##
Claim 25
Dependent Claim
18 words
An organic composition according to claim 13 containing a stabilizing amount of a compound having the formula ##STR37##
Claim 26
Dependent Claim
18 words
An organic composition according to claim 16 containing a stabilizing amount of a compound having the formula ##STR38##
Claim 27
Dependent Claim
18 words
An organic composition according to claim 16 containing a stabilizing amount of a compound having the formula ##STR39##
Claim 28
Dependent Claim
18 words
An organic composition according to claim 16 containing a stabilizing amount of a compound having the formula ##STR40##
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-08-13 | 1983-02-12 | 1983-08-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-08-13 | 1987-02-12 | 1987-08-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-08-13 | 1991-02-12 | 1991-08-14 | $7700.00 | Window Closed / Lapsed |