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US4466916A
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Substituted 2-keto-1,4-diazacycloalkanes
Assignee: Goodrich Corp
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Filing: 1982-06-17
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Granted: 1984-08-21
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Expires: 2002-06-17
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 N1 and N4 atoms of the diaza ring, the remaining portion of the ring having a variable length bridge of two or more carbon atoms, (b) and N-adjacent carbonyl in the fixed two-carbon bridge, and (c) at least one N4-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
2026-11-08 23:43
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C07; C07D; C07D241/00; C07D241/02; C07D241/36; C07D241/38; C07D241/40; C07D241/44; C07D243/00; C07D243/06; C07D243/08; C07D243/10
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
319 words
A bis compound represented by the formula M'--X--M" wherein M' and M" represents two 2-keto-1,4-diazacycloalkane moieties connected through each 1-position of each moiety, or each 4-position of each moiety via a bivalent radical X selected from the group consisting of bivalent alkyl having from 1 to 24 carbon atoms, and the structure ##STR27## and y and z are individually an integer from 1 to about 6; and, wherein M' and M" represent polysubstituted 2-keto-1,4-diazacycloalkanes having a fixed two-carbon bridge between the N 1 and N 4 atoms of the diaza ring having a structural formula selected from ##STR28## 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 having from 1 to 8 carbon atoms; 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; and, R 5 represents alkyl having from 1 to 12 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.
Claim 2
Dependent Claim
319 words
A bis compound represented by the formula M'--X--M" wherein M' and M" represents two 2-keto-1,4-diazacycloalkane moieties connected through each 1-position of each moiety, or each 4-position of each moiety via a bivalent radical X selected from the group consisting of bivalent alkyl having from 1 to 24 carbon atoms, and the structure ##STR27## and y and z are individually an integer from 1 to about 6; and, wherein M' and M" represent polysubstituted 2-keto-1,4-diazacycloalkanes having a fixed two-carbon bridge between the N 1 and N 4 atoms of the diaza ring having a structural formula selected from ##STR28## 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 having from 1 to 8 carbon atoms; 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; and, R 5 represents alkyl having from 1 to 12 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.
Claim 3
Dependent Claim
364 words
A bis compound represented by the formula M'"--X--M"" wherein M'" and M"" represent two 2-keto-1,4-diazacycloalkane moieties connected through each 1-position of each moiety, or each 4-position of each moiety via a bivalent radical X selected from the group consisting of bivalent alkyl having from 1 to 24 carbon atoms, and the structure ##STR29## and y and z are individually an integer from 1 to about 6; and, wherein M'" and M"" represent polysubstituted 2-keto-1,4-diazacycloalkanes having a fixed two-carbon bridge between the N 1 and N 4 atoms of the diaza ring having a structural formula selected from ##STR30## 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 having from 1 to 8 carbon atoms; 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, 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 7 , R 8 additionally also represent hydrogen; and, R 5 , R 6 may when taken together with the carbon atom to which they are attached, form an alkylene ring or a pyridine ring.
Claim 4
Dependent Claim
364 words
A bis compound represented by the formula M'"--X--M"" wherein M'" and M"" represent two 2-keto-1,4-diazacycloalkane moieties connected through each 1-position of each moiety, or each 4-position of each moiety via a bivalent radical X selected from the group consisting of bivalent alkyl having from 1 to 24 carbon atoms, and the structure ##STR29## and y and z are individually an integer from 1 to about 6; and, wherein M'" and M"" represent polysubstituted 2-keto-1,4-diazacycloalkanes having a fixed two-carbon bridge between the N 1 and N 4 atoms of the diaza ring having a structural formula selected from ##STR30## 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 having from 1 to 8 carbon atoms; 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, 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 7 , R 8 additionally also represent hydrogen; and, R 5 , R 6 may when taken together with the carbon atom to which they are attached, form an alkylene ring or a pyridine ring.
Claim 5
Dependent Claim
20 words
The polysubstituted 2-keto-1,4-diazacycloalkanes of claim 1 wherein hydrogen atoms common to fused rings of said bicyclic mono-keto compound are transpositioned.
Claim 6
Dependent Claim
30 words
A polysubstituted compound of claim 1 selected from the group consisting of trans-3,3-pentamethylene-decahydroquinoxalin-2-one; trans-3,3-dimethyl-decahydroquinoxalin-2-one; trans-3,3-dimethyl-N 4 -β-hydroxyethyl-decahydroquinoxalin-2-one; trans-N 1 -dodecyl-3,3-dimethyl-decahydroquinoxalin-2-one; trans-N 1 -benzyl-3,3-dimethyl-decahydroquinoxalin-2-one; trans-N 1 -3,3-pentamethylene-decahydroquinoxalin-2-one; and, trans-3,3-dimethyl-N 4 -β-hydroxyethyl-decahydroquinoxalin-2-one.
Claim 7
Dependent Claim
25 words
A polysubstituted compound of claim 2 selected from the group consisting of 1,2-ethane-bis-(N 1 -3,3,5,5-tetramethyl-2-piperazinone; o-phenylene-bis-N 1 -(3,3,5,5-tetramethyl-2-piperazinone); trans-1,2-cyclohexane-bis-N 1 -(3,3,5,5-tetramethyl-2-piperazinone); and, trans-1,2-cyclohexane-bis-N 1 -(3,5,5-trimethyl-3-isoamyl-2-piperazinone).
References Cited (Backward Citations)
US4292240A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-08-21 | 1988-02-20 | 1988-08-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-08-21 | 1992-02-20 | 1992-08-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-08-21 | 1996-02-20 | 1996-08-21 | $7700.00 | Window Closed / Lapsed |