Patent US4042773A successfully refreshed from Google Patents.
US4042773A
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Peroxide free radical initiators containing ultraviolet light stabilizing groups
Assignee: Arkema Inc
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Filing: 1976-04-27
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Granted: 1977-08-16
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Expires: 1996-04-27
Abstract
Abstract Compounds which contain azo or peroxide linkages as well as the radical of an ultraviolet light stabilizing group are described. These compounds function as polymerization initiators which cause an ultraviolet light stabilization group to be chemically bound to the polymer.
Inventors
- 👤 Chester S. Sheppard
- 👤 Ronald E. MacLeay
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 09:06
CPC Classifications
C; C07; C07F; C07F5/00; C07F5/02; C07F5/04; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/095; C08; C08F; C08F4/00; C08F4/28; C08F4/32; C08F4/34
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
428 words
In the process of preparing a polymer containing an ultraviolet light stabilizer chemically bound to said polymer comprising polymerizing an ethylenically unsaturated monomer capable of being polymerized by free radicals in the presence of a free radical initiator the improvement comprising polymerizing said monomer in the presence of a free radical initiator containing ultraviolet light stabilizing groups and having the formula: (R-O-O).sub.n R' wherein n is 1 to 4 with provisos (a) through (f) recited below, a. when n is 1, R and R' are the same or different and are selected from the group consisting of hydrogen, acyl of 2-20 carbons, aroyl of 7-20 carbons, tert-alkyl of 4-12 carbons, tert-cycloalkyl of 4-12 carbons, tertaralkyl of 9-15 carbons, alkoxycarbonyl of 2-20 carbons, cycloalkoxylcarbonyl of 4-20 carbons, carbamoyl, phenylcarbamoyl, alkylcarbamoyl of 2-13 carbons, cycloalkylcarbamoyl of 4-13 carbons, α-hydroxyalkyl of 2-10 carbons, α-hydroxycycloalkyl of 3-10 carbons, α-hydroperoxyalkyl of 2-10 carbons, α-hydroperoxycycloalkyl of 3-10 carbons, alkylsulfonyl of 4-10 carbons, cycloalkylsulfonyl of 3-12 carbons, tert-(alkyloxyalkyl) of 4-20 carbons, tert-(alkoxycycloalkyl) of 4-20 carbons, Q 3 M, Q 2 M', diethylphosphate, dimethylphosphate, diphenylphosphinic, di-n-octylphosphate, and dibutyl phosphinic; wherein M is selected from silicon, germanium, or tin; M' is boron; and Q is alkyl of 1-11 carbons, phenyl, benzyl, or cyclohexyl; b. when n is 2, R is selected from any of the radicals listed under (a) and R' is selected from the group consisting of carbonyl, alkylidene, of 2-20 carbons, cycloalkylidene of 3-2 carbons, di-tert-alkylene of 6-20 carbons, di-tert-cycloalkylene of 6-20 carbons, di-tert-aralkylene of 12-20 carbons, Q 2 M<, QM'< wherein M is selected from silicon, germanium or tin; M' is boron; and Q is alkyl of 1-11 carbons, phenyl, benzyl, or cyclohexyl; c. when n is 3, R is selected from any of the radicals listed under (a) and R' is selected from the group consisting of tert-aralkyl-di-tert-aralkylene of 15-20 carbons, tert-alkylalkylidene of 4-20 carbons, tert-cycloalkylalkylidene of 4-20 carbons, tert-alkylcycloalkylidene of 4-20 carbons, tert-cycloalkylcycloalkylidene of 6-20 carbons, tert-alkyl-di-tert-alkylene of 10-19 carbons, tert-alkyl-di-tert-cycloalkylene of 10-19 carbons, tert-cycloalkyl-di-tert-alkylene of 10-19 carbons, tert-cycloalkyl-di-tert-cycloalkylene of 10-19 carbons, and QM.tbd.wherein M is selected from silicon, germanium or tin; and Q is selected from alkyl of 1-11 carbons, phenyl, benzyl or cyclohexyl; d. when n is 4, R is selected from any of the radicals listed under (a) and R' is dialkylidene of 5-16 carbons; e. only one of R and R' can be hydrogen; and f. at least one of R and R' contains an ultraviolet light stabilizing radical of a compound selected from the group consisting of ##STR39## wherein R 6 is alkyl of 1-6 carbon atoms.
Claim 2
Dependent Claim
428 words
In the process of preparing a polymer containing an ultraviolet light stabilizer chemically bound to said polymer comprising polymerizing an ethylenically unsaturated monomer capable of being polymerized by free radicals in the presence of a free radical initiator the improvement comprising polymerizing said monomer in the presence of a free radical initiator containing ultraviolet light stabilizing groups and having the formula: (R-O-O).sub.n R' wherein n is 1 to 4 with provisos (a) through (f) recited below, a. when n is 1, R and R' are the same or different and are selected from the group consisting of hydrogen, acyl of 2-20 carbons, aroyl of 7-20 carbons, tert-alkyl of 4-12 carbons, tert-cycloalkyl of 4-12 carbons, tertaralkyl of 9-15 carbons, alkoxycarbonyl of 2-20 carbons, cycloalkoxylcarbonyl of 4-20 carbons, carbamoyl, phenylcarbamoyl, alkylcarbamoyl of 2-13 carbons, cycloalkylcarbamoyl of 4-13 carbons, α-hydroxyalkyl of 2-10 carbons, α-hydroxycycloalkyl of 3-10 carbons, α-hydroperoxyalkyl of 2-10 carbons, α-hydroperoxycycloalkyl of 3-10 carbons, alkylsulfonyl of 4-10 carbons, cycloalkylsulfonyl of 3-12 carbons, tert-(alkyloxyalkyl) of 4-20 carbons, tert-(alkoxycycloalkyl) of 4-20 carbons, Q 3 M, Q 2 M', diethylphosphate, dimethylphosphate, diphenylphosphinic, di-n-octylphosphate, and dibutyl phosphinic; wherein M is selected from silicon, germanium, or tin; M' is boron; and Q is alkyl of 1-11 carbons, phenyl, benzyl, or cyclohexyl; b. when n is 2, R is selected from any of the radicals listed under (a) and R' is selected from the group consisting of carbonyl, alkylidene, of 2-20 carbons, cycloalkylidene of 3-2 carbons, di-tert-alkylene of 6-20 carbons, di-tert-cycloalkylene of 6-20 carbons, di-tert-aralkylene of 12-20 carbons, Q 2 M<, QM'< wherein M is selected from silicon, germanium or tin; M' is boron; and Q is alkyl of 1-11 carbons, phenyl, benzyl, or cyclohexyl; c. when n is 3, R is selected from any of the radicals listed under (a) and R' is selected from the group consisting of tert-aralkyl-di-tert-aralkylene of 15-20 carbons, tert-alkylalkylidene of 4-20 carbons, tert-cycloalkylalkylidene of 4-20 carbons, tert-alkylcycloalkylidene of 4-20 carbons, tert-cycloalkylcycloalkylidene of 6-20 carbons, tert-alkyl-di-tert-alkylene of 10-19 carbons, tert-alkyl-di-tert-cycloalkylene of 10-19 carbons, tert-cycloalkyl-di-tert-alkylene of 10-19 carbons, tert-cycloalkyl-di-tert-cycloalkylene of 10-19 carbons, and QM.tbd.wherein M is selected from silicon, germanium or tin; and Q is selected from alkyl of 1-11 carbons, phenyl, benzyl or cyclohexyl; d. when n is 4, R is selected from any of the radicals listed under (a) and R' is dialkylidene of 5-16 carbons; e. only one of R and R' can be hydrogen; and f. at least one of R and R' contains an ultraviolet light stabilizing radical of a compound selected from the group consisting of ##STR39## wherein R 6 is alkyl of 1-6 carbon atoms.
Claim 3
Dependent Claim
15 words
The process of claim 1 wherein the free radical initiator is OO-t-butyl O-2-(2-hydroxybenzoyl) phenyl monoperoxyphthalate.
Claim 4
Dependent Claim
14 words
The process of claim 1 wherein the free radical initiator is OO-t-butyl O-p-tolyl monoperoxysuccinate.
Claim 5
Dependent Claim
13 words
The process of claim 1 wherein the free radical initiator is di[4-(p-tolyloxycarbonyl)butyryl] peroxide.
Claim 6
Dependent Claim
13 words
The process of claim 1 wherein the free radical initiator is 1,3-dimethyl-3-hydroperoxybutyl 2-cyano-3,3-diphenylacrylate.
Claim 7
Dependent Claim
13 words
The process of claim 1 wherein the free radical initiator is 1,4-di-[1-(3-(4-benzoyl-3-hydroxyphenoxycarbonyl) propionylperox)-1-methylethyl]benzene.
Claim 8
Dependent Claim
13 words
The process of claim 1 wherein the free radical initiator is 1,3,5-tri-[1-(4-(4-benzoyloxyphenoxycarbonyl) butyrylperoxy)-1-methylethyl]benzene.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-08-15 | 1981-02-14 | 1981-08-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-15 | 1985-02-14 | 1985-08-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-15 | 1989-02-14 | 1989-08-16 | $7700.00 | Window Closed / Lapsed |