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US4093809A
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5-Substituted phosphonate hydantoins and derivatives thereof
Assignee: Novartis Corp
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Filing: 1976-06-21
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Granted: 1978-06-06
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Expires: 1996-06-21
Abstract
Abstract Hydantoins of the formula ##STR1## wherein R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, R 2 is ##STR2## R 3 is alkyl of 1 to 8 carbon atoms, and X is a straight or branched chain alkylene of 1 to 4 carbon atoms or a straight or branched chain alkylene of 3 to 6 carbon atoms containing an internal carbamido group; or R 1 and R 2 together are Y where Y is a straight or branched chain alkylene of 4 to 8 carbon atoms having a pendant ##STR3## moiety are prepared by reacting first α,β-unsaturated aldehydes or ketones with alkyl phosphites to form a phosphonate aldehyde or ketone followed by a classical Bucherer hydantoin synthesis. These compounds are intermediates for the preparation of polyglycidyl compounds useful in making flame-retardant epoxy resins. These hydantoins are also intermediates useful in preparing flame-retardant polyesters and polyurethanes.
Inventors
- 👤 Luther A. R. Hall
- 👤 David A. Gordon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 16:26
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/645; C07F9/6503; C07F9/6506
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
95 words
A compound of the formula ##STR24## wherein R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, R 2 is ##STR25## R 3 is alkyl of 1 to 8 carbon atoms, and X is a straight or branched chain alkylene of 1 to 4 carbon atoms or a straight or branched chain alkylene of 3 to 6 carbon atoms containing an internal carbamido group, or R 1 and R 2 together are Y where Y is a straight or branched chain alkylene of 4 to 8 carbon atoms having a pendant ##STR26## moiety.
Claim 2
Dependent Claim
95 words
A compound of the formula ##STR24## wherein R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, R 2 is ##STR25## R 3 is alkyl of 1 to 8 carbon atoms, and X is a straight or branched chain alkylene of 1 to 4 carbon atoms or a straight or branched chain alkylene of 3 to 6 carbon atoms containing an internal carbamido group, or R 1 and R 2 together are Y where Y is a straight or branched chain alkylene of 4 to 8 carbon atoms having a pendant ##STR26## moiety.
Claim 3
Dependent Claim
60 words
A compound according to claim 1 wherein R 1 is hydrogen, methyl or ethyl, R 2 is ##STR27## R 3 is methyl or ethyl, and X is ethylene, --C(CH 3 ) 2 CH 2 -- or --CH 2 CH 2 CONHC(CH 3 ) 2 CH 2 --; or R 1 and R 2 together are Y where Y is ##STR28##
Claim 4
Dependent Claim
13 words
A compound according to claim 1 wherein R 1 is hydrogen or methyl.
Claim 5
Dependent Claim
11 words
A compound according to claim 1 wherein R 3 is ethyl.
Claim 6
Dependent Claim
18 words
A compound according to claim 1 wherein X is ethylene or --C(CH 3 ) 2 CH 2 --.
Claim 7
Dependent Claim
10 words
A compound according to claim 1 wherein Y is ##STR29##
Claim 8
Dependent Claim
46 words
A compound according to claim 1 wherein R 1 is hydrogen or methyl, R 2 is ##STR30## R 3 is ethyl, and X is ethylene or --C(CH 3 ) 2 CH 2 --; or R 1 and R 2 together are Y where Y is ##STR31##
Claim 9
Dependent Claim
9 words
The compound according to claim 1 which is 5-(2-diethylphosphonoethyl)-5-methylhydantoin.
Claim 10
Dependent Claim
9 words
The compound according to claim 1 which is 5-methyl-5-(2-diethylphosphono-2-methylpropyl)hydantoin.
Claim 11
Dependent Claim
9 words
The compound according to claim 1 which is 5-methyl-5-(6-diethylphosphono-2,2-dimethyl-3-aza-4-oxohexyl)hydantoin.
Claim 12
Dependent Claim
10 words
The compound according to claim 1 which is diethyl 7,9,9-trimethyl-1,3-diazaspiro[4.5]decane-2,4-dione-7-ylphosphonate.
Claim 13
Dependent Claim
9 words
The compound according to claim 1 which is 5-(2-diethylphosphonopropyl)hydantoin.
Claim 14
Dependent Claim
102 words
A compound of the formula ##STR32## wherein R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, R 2 is ##STR33## R 3 is alkyl of 1 to 8 carbon atoms, and X is a straight or branched chain alkylene of 1 to 4 carbon atoms or a straight or branched chain alkylene of 3 to 6 carbon atoms containing an internal carbamido group, or R 1 and R 2 together are Y where Y is a straight or branched chain alkylene of 4 to 8 carbon atoms having a pendant ##STR34## and R 4 is hydrogen, methyl or ethyl.
Claim 15
Dependent Claim
102 words
A compound of the formula ##STR32## wherein R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, R 2 is ##STR33## R 3 is alkyl of 1 to 8 carbon atoms, and X is a straight or branched chain alkylene of 1 to 4 carbon atoms or a straight or branched chain alkylene of 3 to 6 carbon atoms containing an internal carbamido group, or R 1 and R 2 together are Y where Y is a straight or branched chain alkylene of 4 to 8 carbon atoms having a pendant ##STR34## and R 4 is hydrogen, methyl or ethyl.
Claim 16
Dependent Claim
64 words
A compound according to claim 13 wherein R 1 is hydrogen, methyl or ethyl, R 2 is ##STR35## R 3 is methyl or ethyl, X is ethylene, --C(CH 3 ) 2 CH 2 -- or --CH 2 CH 2 CONHC(CH 3 ) 2 CH 2 --, or R 1 and R 2 together are Y where Y is ##STR36## and R 4 is hydrogen.
Claim 17
Dependent Claim
13 words
A compound according to claim 13 wherein R 1 is hydrogen or methyl.
Claim 18
Dependent Claim
11 words
A compound according to claim 13 wherein R 3 is ethyl.
Claim 19
Dependent Claim
18 words
A compound according to claim 13 wherein X is ethylene or --C(CH 3 ) 2 CH 2 --.
Claim 20
Dependent Claim
10 words
A compound according to claim 13 wherein Y is ##STR37##
Claim 21
Dependent Claim
11 words
A compound according to claim 13 wherein R 4 is hydrogen.
Claim 22
Dependent Claim
50 words
A compound according to claim 13 wherein R 1 is hydrogen or methyl, R 2 is ##STR38## R 3 is ethyl, X is ethylene or --C(CH 3 ) 2 CH 2 --, or R 1 and R 2 together are Y where Y is ##STR39## and R 4 is hydrogen.
Claim 23
Dependent Claim
9 words
The compound according to claim 13 which is 1,3-di-(β-hydroxyethyl)-5-methyl-5-(2-diethylphosphono-2-methylpropyl)hydantoin.
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) | 1981-06-05 | 1981-12-05 | 1982-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-05 | 1985-12-05 | 1986-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-05 | 1989-12-05 | 1990-06-06 | $7700.00 | Window Closed / Lapsed |