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US3936418A Expired / Lapsed US ⏱️ 0.0 years remaining

Benzotriazole ortho-ester ultraviolet stabilizers and their use in organic compositions

Assignee: Eastman Kodak Co
•
Filing: 1974-10-02
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Granted: 1976-02-03
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Expires: 1994-10-02
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Abstract

Abstract The invention relates to benzotriazole ortho-ester 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 benzotriazole ortho-ester 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, coated on the exterior of the molded article, film or extruded fiber.

Inventors

  • 👤 David Martin Pond
  • 👤 Richard Hsu-Shien Wang

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 11:46
CPC Classifications
C; C07; C07D; C07D249/00; C07D249/16; C07D249/18; C07D249/20; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6515; C07F9/6518; C07F9/65188; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3472; C08K5/3475

Claims Analysis

Total Claims: 42
Claim 1
Independent Claim 337 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of a composition of matter comprising polychromophoric compounds having the formula: (A).sub.x -C wherein A is a group having the structure ##SPC16## wherein 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, carboxy 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 ring and the carbon atom attached to the carbonyl group connecting the heterocyclic aromatic A group with the aromatic C group, a is an integer of 2 to 6 x is an integer of 1 to 6; and C is one of the following: 1. An aromatic group having the formula: ##SPC17## wherein I is the same substituent as listed above and is present in all positions of the benzenoid ring except the carbon atom attached to the carbonyl group connecting the A and C moieties, and said I substituents can all be one of the substituents listed above or different listed substituents; or 2. An aliphatic group having the formula ##EQU3## wherein Q is substituted or unsubstituted acyclic, cyclic or polycyclic aliphatic moiety containing 1 to 18 carbons. I may be a hydrogen, hydroxy, halogen, cyano, C 1 -C 12 substituted or unsubstituted alkyl, amino, alkylamino, dialkylamino, arylamino, diarylamino, alkoxy, aryl or aryloxy group; y is an integer between 2 and 6.
Claim 2
Dependent Claim 337 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of a composition of matter comprising polychromophoric compounds having the formula: (A).sub.x -C wherein A is a group having the structure ##SPC16## wherein 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, carboxy 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 ring and the carbon atom attached to the carbonyl group connecting the heterocyclic aromatic A group with the aromatic C group, a is an integer of 2 to 6 x is an integer of 1 to 6; and C is one of the following: 1. An aromatic group having the formula: ##SPC17## wherein I is the same substituent as listed above and is present in all positions of the benzenoid ring except the carbon atom attached to the carbonyl group connecting the A and C moieties, and said I substituents can all be one of the substituents listed above or different listed substituents; or 2. An aliphatic group having the formula ##EQU3## wherein Q is substituted or unsubstituted acyclic, cyclic or polycyclic aliphatic moiety containing 1 to 18 carbons. I may be a hydrogen, hydroxy, halogen, cyano, C 1 -C 12 substituted or unsubstituted alkyl, amino, alkylamino, dialkylamino, arylamino, diarylamino, alkoxy, aryl or aryloxy group; y is an integer between 2 and 6.
Claim 3
Dependent Claim 12 words
A composition of matter according to claim 1 having the formula: ##SPC18##
Claim 4
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC19##
Claim 5
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC20##
Claim 6
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC21##
Claim 7
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC22##
Claim 8
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC23##
Claim 9
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC24##
Claim 10
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC25##
Claim 11
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC26##
Claim 12
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC27##
Claim 13
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC28##
Claim 14
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC29##
Claim 15
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC30##
Claim 16
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC31##
Claim 17
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC32##
Claim 18
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC33##
Claim 19
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC34##
Claim 20
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC35##
Claim 21
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC36##
Claim 22
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC37##
Claim 23
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC38##
Claim 24
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC39##
Claim 25
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC40##
Claim 26
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC41##
Claim 27
Dependent Claim 20 words
An organic composition according to claim 1 containing a stabilizing amount of a composition of matter having the formula: ##SPC42##
Claim 28
Dependent Claim 206 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of a composition of matter according to claim 1 having the formula: ##SPC43## wherein Q is substituted or unsubstituted acyclic, cyclic or polycyclic aliphatic moiety containing 1 to 18 carbons. y is an integer between 2 and 6. 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, alkoxy, amino, substituted amino, cyano, carboxy and the substituents R 1 and R 2 , R 2 and R 3 , 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 carbonyl linking substituent, said I substituents can all be one of the substituents listed above or different listed substituents.
Claim 29
Dependent Claim 20 words
An organic composition according to claim 27 containing a stabilizing amount of a composition of matter having the formula: ##SPC44##
Claim 30
Dependent Claim 20 words
An organic composition according to claim 27 containing a stabilizing amount of a composition of matter having the formula: ##SPC45##
Claim 31
Dependent Claim 20 words
An organic composition according to claim 27 containing a stabilizing amount of a composition of matter having the formula: ##SPC46##
Claim 32
Dependent Claim 20 words
An organic composition according to claim 27 containing a stabilizing amount of a composition of matter having the formula: ##SPC47##
Claim 33
Dependent Claim 20 words
An organic composition according to claim 27 containing a stabilizing amount of a composition of matter having the formula: ##SPC48##
Claim 34
Dependent Claim 20 words
An organic composition according to claim 27 containing a stabilizing amount of a composition of matter having the formula: ##SPC49##
Claim 35
Dependent Claim 20 words
An organic composition according to claim 27 containing a stabilizing amount of a composition of matter having the formula: ##SPC50##
Claim 36
Dependent Claim 20 words
An organic composition according to claim 27 containing a stabilizing amount of a composition of matter having the formula: ##SPC51##
Claim 37
Dependent Claim 193 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of a composition of matter according to claim 1 having the following formula: ##SPC52## wherein V and W are an integer of 1 to 4; 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, alkoxy, amino, substituted amino, cyano, carboxy and the substituents R 1 and R 2 , R 2 and R 3 , 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 carbonyl linking substituent, said I substituents can all be one of the substituents listed above or different listed substituents.
Claim 38
Dependent Claim 21 words
An organic composition according to claim 36 containing a stabilizing amount of a composition of matter having the following formula: ##SPC53##
Claim 39
Dependent Claim 20 words
An organic composition according to claim 36 containing a stabilizing amount of a composition of matter having the formula: ##SPC54##
Claim 40
Dependent Claim 20 words
An organic composition according to claim 36 containing a stabilizing amount of a composition of matter having the formula: ##SPC55##
Claim 41
Dependent Claim 24 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of a composition of matter having the formula: ##SPC56##
Claim 42
Dependent Claim 24 words
An organic composition susceptible to ultraviolet degradation stabilized against such degradation with a stabilizing amount of a composition of matter having the formula: ##SPC56##

References Cited (Backward Citations)

US3004896A Cited
US3366668A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-02-02 1979-08-04 1980-02-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-02-02 1983-08-04 1984-02-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-02-02 1987-08-04 1988-02-03 $7700.00 Window Closed / Lapsed

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