US3936456A
Expired / Lapsed
US
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Substituted piperazine dione oxyls and hydroxides and polymer compositions stabilized thereby
Assignee: Novartis Corp
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Filing: 1973-07-16
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Granted: 1976-02-03
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Expires: 1993-07-16
Abstract
Abstract Substituted piperazine dione oxyls and hydroxides are stabilizers for synthetic polymeric materials normally subject to deterioration caused by ultraviolet light. The compounds may be prepared by first preparing a substituted piperazine dione with subsequent oxidation of the piperazine dione to yield the oxyl and reduction of the oxyl to yield the hydroxide derivative. Polymeric compositions containing these stabilizers may also contain a hindered phenolic compound. A typical embodiment is 15-n-octadecyl-7-oxyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione.
Inventors
- 👤 Chester E. Ramey
- 👤 John J. Luzzi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:25
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3462
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
145 words
A compound of the formula ##EQU8## wherein X is O or OH; R 1 and R 2 are independently of each other methyl or ethyl or together with the carbon to which they are bound are cyclopentyl or cyclohexyl, which is unsubstituted or substituted with methyl; n is an integer of from 1 to 3; when n is 1, R 3 is hydrogen, alkyl of from 1 to 19 carbon atoms, ##SPC8## or ##EQU9## wherein R 1 , R 2 and X are as defined above; when n is 2, R 3 is the direct bond, alkylene of from 1 to 18 carbon atoms, or ##SPC9## wherein R 4 , r 5 , r 6 , and R 7 are hydrogen or methyl; when n is 3, R 3 is ##SPC10## wherein R 8 , r 9 , and R 10 are hydrogen or methyl.
Claim 2
Dependent Claim
145 words
A compound of the formula ##EQU8## wherein X is O or OH; R 1 and R 2 are independently of each other methyl or ethyl or together with the carbon to which they are bound are cyclopentyl or cyclohexyl, which is unsubstituted or substituted with methyl; n is an integer of from 1 to 3; when n is 1, R 3 is hydrogen, alkyl of from 1 to 19 carbon atoms, ##SPC8## or ##EQU9## wherein R 1 , R 2 and X are as defined above; when n is 2, R 3 is the direct bond, alkylene of from 1 to 18 carbon atoms, or ##SPC9## wherein R 4 , r 5 , r 6 , and R 7 are hydrogen or methyl; when n is 3, R 3 is ##SPC10## wherein R 8 , r 9 , and R 10 are hydrogen or methyl.
Claim 3
Dependent Claim
109 words
A compound according to claim 1 having the formula ##EQU10## wherein X is O or OH; n is an integer of from 1 to 3; when n is 1, R 3 is hydrogen, alkyl of from 1 to 19 carbon atoms, ##SPC11## or ##EQU11## wherein X is as defined above; when n is 2, R 3 is the direct bond, alkylene of from 1 to 18 carbon atoms, or ##SPC12## wherein R 4 , r 5 , r 6 , and R 7 are hydrogen or methyl; when n is 3, R 3 is ##SPC13## wherein R 8 , r 9 , and R 10 are hydrogen or methyl.
Claim 4
Dependent Claim
51 words
A compound according to claim 2 wherein n is 1 or 2; when n is 1, R 3 is hydrogen, alkyl of from 5 to 17 carbon atoms, ##SPC14## or ##EQU12## when n is 2, R 3 is the direct bond, alkylene having from 1 to 10 carbon atoms or ##SPC15##
Claim 5
Dependent Claim
20 words
A compound according to claim 1 wherein R 1 and R 2 are independently of each other methyl or ethyl.
Claim 6
Dependent Claim
58 words
A compound according to claim 1 wherein R 1 and R 2 are methyl; n is 1 or 2; when n is 1, R 3 is hydrogen, alkyl having from 5 to 17 carbon atoms, ##SPC16## or ##EQU13## when n is 2, R 3 is the direct bond, alkylene having from 1 to 10 carbon atoms or ##SPC17##
Claim 7
Dependent Claim
9 words
A compound according to claim 1 which is 15-n-octadecyl-7-oxyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione.
Claim 8
Dependent Claim
9 words
A compound according to claim 1 which is 15-n-octadecyl-7-oxyl-1,9-dimethyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione.
Claim 9
Dependent Claim
9 words
A compound according to claim 1 which is 15-n-octadecyl-7-hydroxy-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione.
Claim 10
Dependent Claim
9 words
A compound according to claim 1 which is 15-n-octadecyl-7-hydroxy-1,9-dimethyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione.
Claim 11
Dependent Claim
9 words
A compound according to claim 1 which is 15-benzyl-7-oxyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione.
Claim 12
Dependent Claim
9 words
A compound according to claim 1 which is 15-benzyl-7-hydroxy-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione.
Claim 13
Dependent Claim
10 words
A compound according to claim 1 which is 15,15'-(2",3",5",6"-tetramethyl p-xylilidenyl)bis(7-oxyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione).
Claim 14
Dependent Claim
10 words
A compound according to claim 1 which is 15,15'-n-dodecamethylene bis(7-oxyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione).
Claim 15
Dependent Claim
10 words
A compound according to claim 1 which is 15,15'-n-dodecamethylene bis(7-hydroxy-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione).
Claim 16
Dependent Claim
10 words
A compound according to claim 1 which is 15,15'-tetramethylene bis(7-oxyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione).
Claim 17
Dependent Claim
9 words
A compound according to claim 1 which is 4-n-octadecyl-1-oxyl-2,2,6,6-tetramethyl-3,5-diketopiperazine.
Claim 18
Dependent Claim
9 words
A compound according to claim 1 which is 15-methyl-7-oxyl-7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione.
Claim 19
Dependent Claim
9 words
A compound according to claim 1 which is 4-benzyl-1-oxyl-2,2,6,6-tetramethyl-3,5-diketopiperazine.
Claim 20
Dependent Claim
9 words
A compound according to claim 1 which is 4,4'(n-dodecamethylene)bis(1-oxyl-2,2,6,6-tetramethyl-3,5-diketopiperazine).
Claim 21
Dependent Claim
9 words
A compound according to claim 1 which is 4,4'(n-dodecamethylene)bis(7-hydroxy12,2,6,6-tetramethyl-3,5-diketopiperazine).
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) | 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 |