US5057612A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N,n'-dihaloimidazolidin-4-ones
Assignee: Auburn University
•
Filing: 1990-01-22
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Granted: 1991-10-15
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Expires: 2010-01-22
Abstract
Abstract Substituted N-halo derivatives of imidazolidin-4-ones having substituents at the 2 and 5 positions of the imidazolidin-4-one ring are described. More particularly, there are described N-chloro, N-bromo, N,N'-dichloro, N,N'-dibromo, and N,N'-bromochloro derivatives of imidazolidin-4-ones having substituents selected from hydrogen, alkyl, alkoxy, hydroxy, phenyl, substituted phenyl, or spiro-substitution at the 2 and 5 positions on the ring. These N-halo compounds are stable, noncorrosive biocides which are resistant to direct sunlight, and are useful as disinfectants, sanitizers, and algae inhibitors.
Inventors
- 👤 Shelby D. Worley
- 👤 Techen Tsao
- 👤 Delbert E. Williams
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 17:51
CPC Classifications
C; C07; C07D; C07D235/00; C07D235/02; C02; C02F; C02F1/00; C02F1/50; C02F1/72; C02F1/76; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D233/32; Y; Y02; Y02W; Y02W10/00; Y02W10/30; Y02W10/37
Claims Analysis
Total Claims: 52
Claim 1
Independent Claim
145 words
N,N'-dihaloimidazolidin-4-one and N-haloimidazolidin-4-one represented by the graphic formula: ##STR4## wherein X and X' are each halogen selected from the group consisting of chlorine and bromine, or one may be hydrogen while the other is halogen selected from the group chlorine and bromine; R 1 , R 2 , R 3 , and R 4 are each selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, phenyl, and substituted phenyl, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substitution selected from the group consisting of pentamethylene and tetramethylene, and mixtures thereof; provided that not more than one of the substituents R 1 -R 4 is hydrogen and provided that when X is chlorine and X' is hydrogen, that not more than three of the groups R 1 -R 4 are methyl.
Claim 2
Dependent Claim
145 words
N,N'-dihaloimidazolidin-4-one and N-haloimidazolidin-4-one represented by the graphic formula: ##STR4## wherein X and X' are each halogen selected from the group consisting of chlorine and bromine, or one may be hydrogen while the other is halogen selected from the group chlorine and bromine; R 1 , R 2 , R 3 , and R 4 are each selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, phenyl, and substituted phenyl, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substitution selected from the group consisting of pentamethylene and tetramethylene, and mixtures thereof; provided that not more than one of the substituents R 1 -R 4 is hydrogen and provided that when X is chlorine and X' is hydrogen, that not more than three of the groups R 1 -R 4 are methyl.
Claim 3
Dependent Claim
62 words
N,N'-dihaloimidazolidin-4-one according to claim 1 wherein X and X' are chlorine, and the substituents R 1 -R 4 are each selected from a group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy, hydroxy, phenyl, para-substituted phenyl, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substitution selected from the group pentamethylene and tetramethylene.
Claim 4
Dependent Claim
43 words
N,N'-dichloroimidazolidin-4-ones according to claim 2 wherein R 1 , R 2 , R 3 , and R 4 are each selected from the group methyl and ethyl, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substituted pentamethylene.
Claim 5
Dependent Claim
1 words
1,3-dichloro-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 6
Dependent Claim
1 words
1,3-dichloro-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 7
Dependent Claim
4 words
1,3-dichloro-2,5 bis (pentamethylene) imidazolidin-4-one.
Claim 8
Dependent Claim
4 words
1,3-dichloro-2,5 bis (pentamethylene) imidazolidin-4-one.
Claim 9
Dependent Claim
1 words
1,3-dichloro-2-pentamethylene-5,5-dimethylimidazolidin-4-one.
Claim 10
Dependent Claim
1 words
1,3-dichloro-2-pentamethylene-5,5-dimethylimidazolidin-4-one.
Claim 11
Dependent Claim
1 words
1,3-dichloro-2,2-dimethyl-5-pentamethyleneimidazolidin-4-one.
Claim 12
Dependent Claim
1 words
1,3-dichloro-2,2-dimethyl-5-pentamethyleneimidazolidin-4-one.
Claim 13
Dependent Claim
1 words
1,3-dichloro-2,2-dimethyl-5,5-diethylimidazolidin-4-one.
Claim 14
Dependent Claim
1 words
1,3-dichloro-2,2-dimethyl-5,5-diethylimidazolidin-4-one.
Claim 15
Dependent Claim
1 words
1,3-dichloro-2-pentamethylene-5,5-diethylimidazolidin-4-one.
Claim 16
Dependent Claim
1 words
1,3-dichloro-2-pentamethylene-5,5-diethylimidazolidin-4-one.
Claim 17
Dependent Claim
1 words
1,3-dichloro-2-pentamethylene-5-ethyl-5-methylimidazolidin-4-one.
Claim 18
Dependent Claim
1 words
1,3-dichloro-2-pentamethylene-5-ethyl-5-methylimidazolidin-4-one.
Claim 19
Dependent Claim
61 words
N,N'-dihaloimidazolidin-4-one according to claim 1 wherein X and X' are bromine, and the substituents R 1 -R 4 are each selected from a group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy, hydroxy, phenyl, para-substituted phenyl, or R 1 ,R 2 and/or R 3 , R 4 may represent spiro-substitution selected from the group pentamethylene and tetramethylene.
Claim 20
Dependent Claim
43 words
N,N'-dibromoimidazolidin-4-ones according to claim 11 wherein R 1 , R 2 , R 3 , and R 4 are each selected from the group methyl and ethyl, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substituted pentamethylene.
Claim 21
Dependent Claim
1 words
1,3-dibromo-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 22
Dependent Claim
1 words
1,3-dibromo-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 23
Dependent Claim
3 words
1,3-dibromo-2,5-bis (pentamethylene) imidazolidin-4-one.
Claim 24
Dependent Claim
3 words
1,3-dibromo-2,5-bis (pentamethylene) imidazolidin-4-one.
Claim 25
Dependent Claim
72 words
N,N'-dihaloimidazolidin-4-one according to claim 1 wherein X is bromine and X' is chlorine or X is chlorine and X' is bromine, and the substituents R 1 -R 4 are each selected from a group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy, hydroxy, phenyl, para-substituted phenyl, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substitution selected from the group pentamethylene and tetramethylene.
Claim 26
Dependent Claim
43 words
N-bromo-N'-chloroimidazolidin-4-ones according to claim 15 wherein R 1 , R 2 , R 3 , and R 4 are each selected from the group methyl and ethyl, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substituted pentamethylene.
Claim 27
Dependent Claim
1 words
1-bromo-3-chloro-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 28
Dependent Claim
1 words
1-bromo-3-chloro-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 29
Dependent Claim
2 words
1-bromo-3-chloro-2,5-bis(pentamethylene) imidazolidin-4-one.
Claim 30
Dependent Claim
2 words
1-bromo-3-chloro-2,5-bis(pentamethylene) imidazolidin-4-one.
Claim 31
Dependent Claim
43 words
N-chloro-N'-bromoimidazolidin-4-ones according to claim 15 wherein R 1 , R 2 , R 3 , and R 4 are each selected from the group methyl and ethyl, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substituted pentamethylene.
Claim 32
Dependent Claim
1 words
1-chloro-3-bromo-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 33
Dependent Claim
1 words
1-chloro-3-bromo-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 34
Dependent Claim
3 words
1-chloro-3-bromo-2,5-bis (pentamethylene) imidazolidin-4-one.
Claim 35
Dependent Claim
3 words
1-chloro-3-bromo-2,5-bis (pentamethylene) imidazolidin-4-one.
Claim 36
Dependent Claim
92 words
N-haloimidazolidin-4-one according to claim 1 wherein either X or X' is halogen selected from the group chlorine and bromine and the other group is hydrogen, the substituents R 1 -R 4 are each selected from a group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy, hydroxy, phenyl, para-substituted phenyl, but provided that not more than three are methyl when X is chlorine and X' is hydrogen, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substitution selected from the group pentamethylene and tetramethylene.
Claim 37
Dependent Claim
60 words
N-chloroimidazolidin-4-one according to claim 22 wherein R 1 , R 2 , R 3 , and R 4 are each selected from the group methyl and ethyl, but provided that not more than three are methyl when X is chlorine and X' is hydrogen, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substituted pentamethylene.
Claim 38
Dependent Claim
3 words
1-chloro-2,5-bis (pentamethylene) imidazolidin-4-one.
Claim 39
Dependent Claim
3 words
1-chloro-2,5-bis (pentamethylene) imidazolidin-4-one.
Claim 40
Dependent Claim
1 words
3-chloro-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 41
Dependent Claim
1 words
3-chloro-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 42
Dependent Claim
3 words
3-chloro-2,5-bis (pentamethylene) imidazolidin-4-one.
Claim 43
Dependent Claim
3 words
3-chloro-2,5-bis (pentamethylene) imidazolidin-4-one.
Claim 44
Dependent Claim
43 words
N-bromoimidazolidin-4-one according to claim 22 wherein R 1 , R 2 , R 3 , and R 4 are each selected from the group methyl and ethyl, or R 1 , R 2 and/or R 3 , R 4 may represent spiro-substituted pentamethylene.
Claim 45
Dependent Claim
1 words
1-bromo-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 46
Dependent Claim
1 words
1-bromo-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 47
Dependent Claim
2 words
1-bromo-2,5-bis (pentamethylene)imidazolidin-4-one.
Claim 48
Dependent Claim
2 words
1-bromo-2,5-bis (pentamethylene)imidazolidin-4-one.
Claim 49
Dependent Claim
1 words
3-bromo-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 50
Dependent Claim
1 words
3-bromo-2,2,5,5-tetramethylimidazolidin-4-one.
Claim 51
Dependent Claim
3 words
3-bromo-2,5-bis (pentamethylene) imidazolidin-4-one.
Claim 52
Dependent Claim
3 words
3-bromo-2,5-bis (pentamethylene) imidazolidin-4-one.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-10-14 | 1995-04-15 | 1995-10-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-10-14 | 1999-04-15 | 1999-10-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-10-14 | 2003-04-15 | 2003-10-15 | $7700.00 | Window Closed / Lapsed |