US4292240A
Expired / Lapsed
US
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2-Keto-1,4-diazacycloalkanes
Assignee: Goodrich Corp
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Filing: 1979-10-26
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Granted: 1981-09-29
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Expires: 1999-10-26
Abstract
Abstract Novel polysubstituted 2-keto-1,4-diazacycloalkanes are powerful stabilizers for materials subject to ultraviolet (UV) light degradation, particularly for polyolefins. The cyclic 2-keto compounds of this invention have (a) a fixed two-carbon bridge between the N 1 and N 4 atoms of the diaza ring, the remaining portion of the ring having a variable length bridge of two or more carbon atoms, (b) an N-adjacent carbonyl in the fixed two-carbon bridge, and (c) at least one N 4 -adjacent carbon atom of the diaza ring is polysubstituted, that is, has two substituents which may be cyclizable. Compositions containing (a) the polysubstituted 2-keto-1,4-diazacycloalkanes of this invention, and (b) prior art polysubstituted 2-keto-1,4-diazacycloalkanes, exhibit excellent stability to UV light.
Inventors
- 👤 John T. Lai
- 👤 Pyong N. Son
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 16:16
CPC Classifications
C; C07; C07D; C07D243/00; C07D243/06; C07D243/08; C07D241/00; C07D241/02; C07D241/36; C07D241/38; C07D241/40; C07D241/44; C07D243/10; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442
Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
303 words
A compound having one of the formulae ##STR27## wherein, R 1 and R 4 independently represent hydrogen, alkyl having from 1 to 24 carbon atoms, hydroxyalkyl having from 1 to 12 carbon atoms, haloalkyl having from 1 to 12 carbon atoms, cyanoalkyl having from 2 to 12 carbon atoms, aminoalkyl having from 1 to 12 carbon atoms, alkenyl having from 2 to 14 carbon atoms, and unsubstituted hydrocarbon aralkyl having from 7 to 14 carbon atoms; R 4 optionally also represents oxygen, hydroxy or alkoxy; R 2 and R 3 independently represent alkyl having from 1 to 12 carbon atoms, haloalkyl having from 1 to 12 carbon atoms, cyanoalkyl having from 2 to 12 carbon atoms, aminoalkyl having from 1 to 12 carbon atoms, cycloalkyl having from 5 to 14 carbon atoms, hydroxy-cycloalkyl having from 5 to 14 carbon atoms, alkenyl having from 2 to 14 carbon atoms, and unsubstituted hydrocarbon aralkyl having from 7 to 14 carbon atoms; R 5 , R 6 , R 7 , R 8 independently represent alkyl having from 1 to 12 carbon atoms, haloalkyl having from 1 to 12 carbon atoms, cyanoalkyl having from 2 to 12 carbon atoms, aminoalkyl having from 1 to 12 carbon atoms, alkenyl having from 2 to 14 carbon atoms, and unsubstituted hydrocarbon aralkyl having from 7 to 14 carbon atoms; so that when R 2 , R 3 is cyclized having from 4 to 6 unsubstituted methylene groups, and R 5 , R 6 is also cyclized having from 4 to 6 unsubstituted methylene groups, each cyclized substituent is different; R 7 , R 8 additionally also represent hydrogen; and, R 7 , R 8 , may when taken together with the carbon atom to which they are attached, form a polymethylene ring having from 5 to 6 carbon atoms.
Claim 2
Dependent Claim
303 words
A compound having one of the formulae ##STR27## wherein, R 1 and R 4 independently represent hydrogen, alkyl having from 1 to 24 carbon atoms, hydroxyalkyl having from 1 to 12 carbon atoms, haloalkyl having from 1 to 12 carbon atoms, cyanoalkyl having from 2 to 12 carbon atoms, aminoalkyl having from 1 to 12 carbon atoms, alkenyl having from 2 to 14 carbon atoms, and unsubstituted hydrocarbon aralkyl having from 7 to 14 carbon atoms; R 4 optionally also represents oxygen, hydroxy or alkoxy; R 2 and R 3 independently represent alkyl having from 1 to 12 carbon atoms, haloalkyl having from 1 to 12 carbon atoms, cyanoalkyl having from 2 to 12 carbon atoms, aminoalkyl having from 1 to 12 carbon atoms, cycloalkyl having from 5 to 14 carbon atoms, hydroxy-cycloalkyl having from 5 to 14 carbon atoms, alkenyl having from 2 to 14 carbon atoms, and unsubstituted hydrocarbon aralkyl having from 7 to 14 carbon atoms; R 5 , R 6 , R 7 , R 8 independently represent alkyl having from 1 to 12 carbon atoms, haloalkyl having from 1 to 12 carbon atoms, cyanoalkyl having from 2 to 12 carbon atoms, aminoalkyl having from 1 to 12 carbon atoms, alkenyl having from 2 to 14 carbon atoms, and unsubstituted hydrocarbon aralkyl having from 7 to 14 carbon atoms; so that when R 2 , R 3 is cyclized having from 4 to 6 unsubstituted methylene groups, and R 5 , R 6 is also cyclized having from 4 to 6 unsubstituted methylene groups, each cyclized substituent is different; R 7 , R 8 additionally also represent hydrogen; and, R 7 , R 8 , may when taken together with the carbon atom to which they are attached, form a polymethylene ring having from 5 to 6 carbon atoms.
Claim 3
Dependent Claim
57 words
A compound of claim 1 selected from the group consisting of 1,2-ethane-bis-(N 1 -3,3,5,5-tetramethyl-2-piperazinone); N 1 -dodecyl-3,3,5,5tetramethyl-2-piperazinone; N 1 -t-octyl-3,3,5,5tetramethyl-2-piperazinone; N 4 -t-octyl-3,3,6,6-tetramethyl-2-piperazinone; N 1 -phenyl-3,3,5,5-tetramethyl-2-piperazinone; N 1 -t-butyl-3,3-dimethyl-5,5-pentamethylene-2-piperazinone; N 1 -t-butyl-3,3-dimethyl-5,5-pentamethyl-2-piperazinone; N 1 -butyl-3,3,5,5,7-pentamethyl-1,4-diazepine-2-one; N 1 -t-octyl-3,3-pentamethylene-5,5-dimethyl-2-piperazinone-N 4 -oxyl; N 1 -isopropyl-3,3,5-trimethyl-4-isobutyl-2-piperazinone; N 1 -isopropyl-3,5,5-trimethyl-4-phenyl-2-piperazinone; 3-isobutyl-N 4 -hydroxy-N 1 -isopropyl-3,5,5-trimethyl-2-piperazinone; and, 3-ethyl-N 4 -hydroxy-N 1 -isopropyl-3,5,5-trimethyl-2-piperazinone.
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) | 1984-09-28 | 1985-03-30 | 1985-09-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-28 | 1989-03-30 | 1989-09-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-28 | 1993-03-30 | 1993-09-29 | $7700.00 | Window Closed / Lapsed |