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Branched chain nonyl and dodecyl isomeric mixtures of 2-(5'-nonyl, or dodecyl-2'-hydroxyphenyl)benzotriazole as UV stabilizers
Assignee: GAF Corp
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Filing: 1976-09-28
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Granted: 1978-12-12
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Expires: 1996-09-28
Abstract
Abstract This invention relates to a stabilization composition, particularly adapted to prevent deterioration resulting from exposure to heat and light in polymeric materials, paints and dyes consisting essentially of a normally liquid, branched chain nonyl, or dodecyl isomeric mixture of 2-(5'-nonyl, or -dodecyl-2'-hydroxy-phenyl) benzotriazole; to the method of preparing said stabilization composition and to the stabilized products having between about 0.05 and about 15 weight percent of said stabilization composition incorporated therein.
Inventors
- 👤 Albert F. Strobel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 18:47
CPC Classifications
A; A61; A61Q; A61Q17/00; A61Q17/04; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/494; A61K8/496; C; C07; C07D; C07D249/00; C07D249/16; C07D249/18; C07D249/20; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3472; C08K5/3475; C09; C09K; C09K15/00; C09K15/04; C09K15/30; Y; Y10; Y10S; Y10S8/00; Y10S8/92; Y10S8/928
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
44 words
A normally liquid composition for stabilizing heat and light sensitive materials consisting essentially of branched-chain isomers of hydroxyphenyl benzotriazoles selected from the group consisting of a branched chain dodecyl isomeric mixture of 2-(5'-dodecyl-2'-hydroxyphenyl) benzotriazoles and a branched chain nonyl isomeric mixture of 2-(5'-nonyl-2'-hyroxyphenyl) benzotriazoles.
Claim 2
Dependent Claim
44 words
A normally liquid composition for stabilizing heat and light sensitive materials consisting essentially of branched-chain isomers of hydroxyphenyl benzotriazoles selected from the group consisting of a branched chain dodecyl isomeric mixture of 2-(5'-dodecyl-2'-hydroxyphenyl) benzotriazoles and a branched chain nonyl isomeric mixture of 2-(5'-nonyl-2'-hyroxyphenyl) benzotriazoles.
Claim 3
Dependent Claim
20 words
The composition of claim 1 wherein the branched chain isomeric mixtures are substantially free of their respective straight chain isomers.
Claim 4
Dependent Claim
116 words
A process for the preparation of the composition of claim 2 which comprises: (a) Coupling a 2-nitrophenyl diazonium salt with a normally liquid mixture of branched chain isomers of phenol selected from the group consisting of the branched chain nonyl isomers of 4-nonyl phenol and the branched chain dodecyl isomers of 4-dodecyl phenol in the presence of glacial acetic acid at a pH from about 3 to about 5.5 to form an oily liquid; and (b) Cyclizing the 2-(2' nitrophenylazo)-4-nonyl phenols and 2-(2' nitrophenylazo)-4-dodecyl phenols respectively formed to the corresponding triazoles in a solution with a zinc catalyst in the presence of an aqueous inorganic hydroxide which forms the corresponding normally liquid mixture of claim 2.
Claim 5
Dependent Claim
95 words
The process of claim 3 wherein the product of step b) is further contacted with from about 5 to about 30 mole percent of an organic anhydride selected from the group of alkyl anhydride having from 4 to 8 carbon atoms, phthalic anhydride and succinic anhydride and distilling the resulting liquid under vacuum, 0.01 to 0.15 mm Hg pressure, to separate a distillate fraction boiling between about 180° C. and about 250° C. and recovering the corresponding normally liquid mixture of branched chain isomers selected from the group consisting of 2-(5'-nonyl-2'-hydroxyphenyl) benzotraizole and 2-(5'-dodecyl-2'-hydroxyphenyl) benzotriazole.
Claim 6
Dependent Claim
12 words
The process of claim 4 wherein the organic anhydride is acetic anhydride.
Claim 7
Dependent Claim
61 words
The process of claim 4 wherein the normally liquid distilled mixture is contacted with oxygen and redistilled under 0.02 mm to 0.06 mm Hg pressure to separate a distillate fraction boiling between about 180° C. and about 230° C. and recovering the correspondingly normally liquid mixture of branched chain isomers selected from the group consisting of 2-(5'-nonyl-2'-hydroxyphenyl) benzotriazole and 2-(5'-dodecyl-2'-hydroxyphenyl) benzotriazole.
Claim 8
Dependent Claim
26 words
The process of claim 6 wherein the normally liquid distilled mixture is contacted with air at a temperature between about 50° C. and about 150° C.
Claim 9
Dependent Claim
20 words
The composition of claim 1 wherein the branched chain isomeric mixture is a branched chain nonyl isomeric mixture of 2-(5'-nonyl-2'-hydroxyphenyl)benzotriazoles.
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) | 1981-12-11 | 1982-06-12 | 1982-12-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-11 | 1986-06-12 | 1986-12-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-11 | 1990-06-12 | 1990-12-12 | $7700.00 | Window Closed / Lapsed |