US4007157A
Expired / Lapsed
US
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Substituted piperazines and polymeric compositions stabilized thereby
Assignee: Novartis Corp
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Filing: 1975-06-27
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Granted: 1977-02-08
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Expires: 1995-06-27
Abstract
Abstract Substituted piperazines are stabilizers for synthetic polymeric materials normally subject to deterioration caused by ultraviolet light. The compounds are prepared by the alkylation reaction between a substituted piperazine dione and an organic halide followed by reduction with lithium aluminum hydride. Polymeric compsitions containing these stabilizers may also contain a hindered phenolic compound. A typical embodiment is 15,15'-dodecamethylene-bis(7,15-diazadispiro[5,1,5,3]hexadecane).
Inventors
- 👤 Chester E. Ramey
- 👤 John J. Luzzi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 08:34
CPC Classifications
C; C07; C07D; C07D241/00; C07D241/36; C07D241/38; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3462; C08K5/3465
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
78 words
A compound of the formula ##STR16## wherein R 1 and R 2 together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; n is an integer of from 1 to 2; when n is 1, R 3 is hydrogen, alkyl of from 1 to 20 carbon atoms or benzyl; when n is 2, R 3 is alkylene of from 1 to 20 carbon atoms.
Claim 2
Dependent Claim
78 words
A compound of the formula ##STR16## wherein R 1 and R 2 together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; n is an integer of from 1 to 2; when n is 1, R 3 is hydrogen, alkyl of from 1 to 20 carbon atoms or benzyl; when n is 2, R 3 is alkylene of from 1 to 20 carbon atoms.
Claim 3
Dependent Claim
77 words
A compound of the formula ##STR17## wherein R 1 and R 2 together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; n is an integer of from 1 to 2; when n is 1, R 3 is hydrogen or alkyl of from 1 to 20 carbon atoms; when n is 2, R 3 is alkylene of from 1 to 20 carbon atoms.
Claim 4
Dependent Claim
77 words
A compound of the formula ##STR17## wherein R 1 and R 2 together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; n is an integer of from 1 to 2; when n is 1, R 3 is hydrogen or alkyl of from 1 to 20 carbon atoms; when n is 2, R 3 is alkylene of from 1 to 20 carbon atoms.
Claim 5
Dependent Claim
51 words
A compound according to claim 2 having the formula ##STR18## wherein n is an integer of from 1 to 2; when n is 1, R 3 is hydrogen, alkyl of from 1 to 20 carbon atoms; when n is 2, R 3 is alkylene of from 1 to 20 carbon atoms.
Claim 6
Dependent Claim
23 words
A compound according to claim 3 wherein n is 1; R 3 is hydrogen or alkyl having from 6 to 18 carbon atoms.
Claim 7
Dependent Claim
21 words
A compound according to claim 3 wherein n is 2; R 3 is alkylene having from 2 to 12 carbon atoms.
Claim 8
Dependent Claim
9 words
A compound according to claim 2 which is 7,15-diazadispirol[5,1,5,3]hexadecane.
Claim 9
Dependent Claim
9 words
A compound according to claim 2 which is 15-n-octadecyl-7,15-diazadispiro[5,1,5,3]hexadecane.
Claim 10
Dependent Claim
10 words
A compound according to claim 2 which is 15-n-octadecyl-1,9-dimethyll-7,15-diazadispiro[5,1,5,3] hexadecane.
Claim 11
Dependent Claim
9 words
A compound according to claim 1 which is 15-benzyl-7,15-diazadispiro[5,1,5,3]hexadecane.
Claim 12
Dependent Claim
11 words
A compound according to claim 2 which is 15,15'-dodecamethylene bis(7,15-diazadispiro[5,1,5,3] hexadecane).
Claim 13
Dependent Claim
11 words
A compound according to claim 2 which is 15,15'-octamethylene bis(7,15-diazadispiro[5,1,5,3] hexadecane).
Claim 14
Dependent Claim
11 words
A compound according to claim 2 which is 15,15':tetramethylene bis(7,15-diazadispiro[5,1,5,3] hexadecane).
Claim 15
Dependent Claim
9 words
A compound according to claim 2 which is 15-methyl-7,15-diazadispiro[5,1,5,3]hexadecane.
Claim 16
Dependent Claim
9 words
A compound according to claim 2 which is 15-n-octyl-7,15-diazadispiro[5,1,5,3]hexadecane.
Claim 17
Dependent Claim
38 words
A composition of matter stabilized against ultraviolet deterioration consisting essentially of a synthetic organic polymer normally subject to ultraviolet deterioration containing from 0.0l to 2% by weight of the polymer of a stabilizing compound according to claim 1.
Claim 18
Dependent Claim
47 words
A composition of matter stabilized against ultraviolet deterioration consisting essentially of a synthetic organic polymer normally subject to ultraviolet deterioration containing a stabilizing amount of a hindered phenolic compound and from about 0.0l to 2% by weight of the polymer of a compound according to claim 1.
Claim 19
Dependent Claim
11 words
A composition of claim 16 wherein the polymer is a polyolefin.
Claim 20
Dependent Claim
10 words
A composition of claim 17 wherein the polyolefin is polypropylene.
Claim 21
Dependent Claim
19 words
A composition of claim 17 wherein the hindered phenolic compound is selected from n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, di-n-octadecyl(3,5-di-t-butyl-4-hydroxybenzyl)phosphonate, pentaerythritol-tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], and tris-(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate.
Claim 22
Dependent Claim
10 words
A composition of claim 17 wherein the antixodiant is di-n-octadecyl(3,5-di-t-butyl-4-hydroxybenzyl)phosphonate.
Claim 23
Dependent Claim
14 words
A composition of claim 17 wherein the substituted piperazine stabilizing compound is 15,15'-dodecamethylene bis(7,15-diazadispiro[5.1.5.3]hexadecane).
Claim 24
Dependent Claim
14 words
A composition of claim 17 wherein the substituted piperazine stabilizing compound is 15,15'-octamethylene bis(7,15-diazadispiro[5.1.5.3]hexadecane).
Claim 25
Dependent Claim
14 words
A composition of claim 17 wherein the substituted piperazine stabilizing compound is 15,15'-tetramethylene bis(7,15-diazadispiro[5.1.5.3]hexadecane).
References Cited (Backward Citations)
US3318876A
Cited
US3920659A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-08 | 1980-08-09 | 1981-02-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-08 | 1984-08-09 | 1985-02-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-08 | 1988-08-09 | 1989-02-08 | $7700.00 | Window Closed / Lapsed |