US4031127A
Expired / Lapsed
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Acyl hydrazino thiourea derivatives as photographic nucleating agents
Assignee: Eastman Kodak Co
•
Filing: 1976-06-29
•
Granted: 1977-06-21
•
Expires: 1996-06-29
Abstract
Abstract Photographic nucleating agents are disclosed of the formula ##STR1## wherein R is a hydrogen, phenyl, alkylphenyl, cyanophenyl, halophenyl, alkoxyphenyl, alkyl, cycloalkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent; R 1 is a phenylene or alkyl, halo- or alkoxy substituted phenylene group; R 2 is an alkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent having up to 18 carbon atoms; a cycloalkyl substituent; phenyl or naphthyl; an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent or ##STR2## R 3 is hydrogen, benzyl, alkoxybenzyl, halobenzyl or alkylbenzyl; THE ALKYL MOIETIES, EXCEPT AS OTHERWISE NOTED, IN EACH INSTANCE INCLUDE FROM 1 TO 6 CARBON ATOMS; AND The cycloalkyl moieties have from 3 to 10 carbon atoms.
Inventors
- 👤 Ronald E. Leone
- 👤 II Wayne W. Weber
- 👤 Donald P. Wrathall
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 18:39
CPC Classifications
C; C07; C07C; C07C335/00; C07C335/04; C07C335/16; C07C335/20; G; G03; G03C; G03C1/00; G03C1/005; G03C1/485; G03C1/48538; G03C1/48546; G03C1/48561
Claims Analysis
Total Claims: 82
Claim 1
Independent Claim
103 words
A compound having the formula ##STR45## wherein R is a hydrogen, phenyl, alkylphenyl, cyanophenyl, halophenyl, alkoxyphenyl, alkyl, cycloalkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent; R 1 is a phenylene or alkyl, halo- or alkoxy substituted phenylene; R 2 is an alkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent having up to 18 carbon atoms; a cycloalkyl substituent; phenyl or naphthyl; an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent or ##STR46## R 3 is hydrogen, benzyl, alkoxybenzyl, halobenzyl or alkylbenzyl; said alkyl moieties, except as otherwise noted, in each instance include from 1 to 6 carbon atoms; and said cycloalkyl moieties have from 3 to 10 carbon atoms.
Claim 2
Dependent Claim
103 words
A compound having the formula ##STR45## wherein R is a hydrogen, phenyl, alkylphenyl, cyanophenyl, halophenyl, alkoxyphenyl, alkyl, cycloalkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent; R 1 is a phenylene or alkyl, halo- or alkoxy substituted phenylene; R 2 is an alkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent having up to 18 carbon atoms; a cycloalkyl substituent; phenyl or naphthyl; an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent or ##STR46## R 3 is hydrogen, benzyl, alkoxybenzyl, halobenzyl or alkylbenzyl; said alkyl moieties, except as otherwise noted, in each instance include from 1 to 6 carbon atoms; and said cycloalkyl moieties have from 3 to 10 carbon atoms.
Claim 3
Dependent Claim
20 words
A compound according to claim 1 wherein said alkyl moieties of R consist of from 1 to 4 carbon atoms.
Claim 4
Dependent Claim
13 words
A compound according to claim 1 wherein R 1 is a para-phenylene group.
Claim 5
Dependent Claim
101 words
A compound of the formula: ##STR47## wherein R is a hydrogen, phenyl, alkylphenyl, cyanophenyl, halophenyl, alkoxyphenyl, alkyl, cycloalkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent; R 1 is a phenylene or alkyl, halo- or alkoxy substituted phenylene; R 2 is an alkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent having up to 18 carbon atoms; a cycloalkyl substituent; phenyl or naphthyl; or an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent; R 3 is benzyl, alkoxybenzyl, halobenzyl or alkylbenzyl; said alkyl moieties, except as otherwise noted, in each instance include from 1 to 6 carbon atoms; and said cycloalkyl moieties have from 3 to 10 carbon atoms.
Claim 6
Dependent Claim
101 words
A compound of the formula: ##STR47## wherein R is a hydrogen, phenyl, alkylphenyl, cyanophenyl, halophenyl, alkoxyphenyl, alkyl, cycloalkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent; R 1 is a phenylene or alkyl, halo- or alkoxy substituted phenylene; R 2 is an alkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent having up to 18 carbon atoms; a cycloalkyl substituent; phenyl or naphthyl; or an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent; R 3 is benzyl, alkoxybenzyl, halobenzyl or alkylbenzyl; said alkyl moieties, except as otherwise noted, in each instance include from 1 to 6 carbon atoms; and said cycloalkyl moieties have from 3 to 10 carbon atoms.
Claim 7
Dependent Claim
20 words
A compound according to claim 4 wherein said alkyl moieties of R consist of from 1 to 4 carbon atoms.
Claim 8
Dependent Claim
30 words
A compound according to claim 4 wherein R 2 is an alkyl substituent having from 1 to 12 carbon atoms; a cyclohexyl substituent; phenyl; or 4-alkylphenyl, 4-halophenyl or 4-alkoxyphenyl substituent.
Claim 9
Dependent Claim
12 words
A compound according to claim 4 wherein R 1 is a para-phenylene.
Claim 10
Dependent Claim
1 words
1-[4-(2-Acetylhydrazino)phenyl]-1-benzyl-3-phenylthiourea.
Claim 11
Dependent Claim
1 words
1-[4-(2-Acetylhydrazino)phenyl]-1-benzyl-3-phenylthiourea.
Claim 12
Dependent Claim
1 words
1-[4-(2-Acetylhydrazino)phenyl]-1-(4-methoxybenzyl)-3-phenylthiourea.
Claim 13
Dependent Claim
1 words
1-[4-(2-Acetylhydrazino)phenyl]-1-(4-methoxybenzyl)-3-phenylthiourea.
Claim 14
Dependent Claim
95 words
A compound having the formula ##STR48## wherein R is a hydrogen, phenyl, alkylphenyl, cyanophenyl, halophenyl, alkoxyphenyl, alkyl, cycloalkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent; R 1 is a phenylene or alkyl, halo- or alkoxy substituted phenylene group; R 2 is an alkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent having up to 18 carbon atoms; a cycloalkyl substituent; phenyl or naphthyl; an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent or ##STR49## said alkyl moieties, except as otherwise noted, in each instance include from 1 to 6 carbon atoms; and said cycloalkyl moieties have from 3 to 10 carbon atoms.
Claim 15
Dependent Claim
95 words
A compound having the formula ##STR48## wherein R is a hydrogen, phenyl, alkylphenyl, cyanophenyl, halophenyl, alkoxyphenyl, alkyl, cycloalkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent; R 1 is a phenylene or alkyl, halo- or alkoxy substituted phenylene group; R 2 is an alkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent having up to 18 carbon atoms; a cycloalkyl substituent; phenyl or naphthyl; an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent or ##STR49## said alkyl moieties, except as otherwise noted, in each instance include from 1 to 6 carbon atoms; and said cycloalkyl moieties have from 3 to 10 carbon atoms.
Claim 16
Dependent Claim
20 words
A compound according to claim 10 wherein said alkyl moieties of R consist of from 1 to 4 carbon atoms.
Claim 17
Dependent Claim
31 words
A compound according to claim 10 wherein R 2 is an alkyl substituent having from 1 to 12 carbon atoms; a cyclohexyl substituent; phenyl; or a 4-alkylphenyl, 4-halophenyl or 4-alkoxyphenyl substituent.
Claim 18
Dependent Claim
26 words
A compound according to claim 10 wherein R 1 is a para-phenylene or para-phenylene substituted in the 3 position with an alkyl, halo- or alkoxy substituent.
Claim 19
Dependent Claim
93 words
A compound having the formula ##STR50## wherein R is a hydrogen, phenyl, 4-alkylphenyl, 4-halophenyl, 4-alkoxyphenyl, alkyl, cyclohexyl or phenylalkyl substituent; wherein said alkyl moieties have from 1 to 4 carbon atoms; R 1 is a para-phenylene or a 3 position alkyl, halo- or alkoxy substituted para-phenyene group; and R 2 is an alkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent having up to 2 carbon atoms; a cyclohexyl substituent; phenyl; or a 4-alkylphenyl, 4-halophenyl or 4-alkoxyphenyl substituent; wherein said alkyl moieties, except as otherwise noted, in each instance include from 1 to 6 carbon atoms.
Claim 20
Dependent Claim
93 words
A compound having the formula ##STR50## wherein R is a hydrogen, phenyl, 4-alkylphenyl, 4-halophenyl, 4-alkoxyphenyl, alkyl, cyclohexyl or phenylalkyl substituent; wherein said alkyl moieties have from 1 to 4 carbon atoms; R 1 is a para-phenylene or a 3 position alkyl, halo- or alkoxy substituted para-phenyene group; and R 2 is an alkyl, haloalkyl, alkoxyalkyl or phenylalkyl substituent having up to 2 carbon atoms; a cyclohexyl substituent; phenyl; or a 4-alkylphenyl, 4-halophenyl or 4-alkoxyphenyl substituent; wherein said alkyl moieties, except as otherwise noted, in each instance include from 1 to 6 carbon atoms.
Claim 21
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-phenylthiourea.
Claim 22
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-phenylthiourea.
Claim 23
Dependent Claim
1 words
1-[4-(2-Acetylhydrazino)phenyl]-3-phenylthiourea.
Claim 24
Dependent Claim
1 words
1-[4-(2-Acetylhydrazino)phenyl]-3-phenylthiourea.
Claim 25
Dependent Claim
1 words
1-[4-(2-Benzoylhydrazino)phenyl]-3-phenylthiourea.
Claim 26
Dependent Claim
1 words
1-[4-(2-Benzoylhydrazino)phenyl]-3-phenylthiourea.
Claim 27
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-methylthiourea.
Claim 28
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-methylthiourea.
Claim 29
Dependent Claim
1 words
1-[4-(2-Acetylhydrazino)phenyl]-3-ethylthiourea.
Claim 30
Dependent Claim
1 words
1-[4-(2-Acetylhydrazino)phenyl]-3-ethylthiourea.
Claim 31
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-butylthiourea.
Claim 32
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-butylthiourea.
Claim 33
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-cyclohexylthiourea.
Claim 34
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-cyclohexylthiourea.
Claim 35
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-benzylthiourea.
Claim 36
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-benzylthiourea.
Claim 37
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-heptylthiourea.
Claim 38
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-heptylthiourea.
Claim 39
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-decylthiourea.
Claim 40
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-decylthiourea.
Claim 41
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-(4-cyanophenyl)thiourea.
Claim 42
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-(4-cyanophenyl)thiourea.
Claim 43
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-(4-methoxyphenyl)thiourea.
Claim 44
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)phenyl]-3-(4-methoxyphenyl)thiourea.
Claim 45
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)-3-methoxyphenyl]-3-phenylthiourea.
Claim 46
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)-3-methoxyphenyl]-3-phenylthiourea.
Claim 47
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)-3-methoxyphenyl]-3-butylthiourea.
Claim 48
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)-3-methoxyphenyl]-3-butylthiourea.
Claim 49
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)-3-methoxyphenyl]-3-cyclohexylthiourea.
Claim 50
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)-3-methoxyphenyl]-3-cyclohexylthiourea.
Claim 51
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)-3-methoxyphenyl]-3-(4-methoxyphenyl)thiourea.
Claim 52
Dependent Claim
1 words
1-[4-(2-Formylhydrazino)-3-methoxyphenyl]-3-(4-methoxyphenyl)thiourea.
Claim 53
Dependent Claim
1 words
1-[4-(2-Trifluoroacetylhydrazino)phenyl]-3-phenylthiourea.
Claim 54
Dependent Claim
1 words
1-[4-(2-Trifluoroacetylhydrazino)phenyl]-3-phenylthiourea.
Claim 55
Dependent Claim
1 words
1-{4-[2-(4-Cyanobenzoyl)hydrazino]phenyl}-3-phenylthiourea.
Claim 56
Dependent Claim
1 words
1-{4-[2-(4-Cyanobenzoyl)hydrazino]phenyl}-3-phenylthiourea.
Claim 57
Dependent Claim
1 words
1-{-4-[2-(4-Chlorobenzoyl)hydrazino]phenyl}-3-phenylthiourea.
Claim 58
Dependent Claim
1 words
1-{-4-[2-(4-Chlorobenzoyl)hydrazino]phenyl}-3-phenylthiourea.
Claim 59
Dependent Claim
1 words
1-{4-[2-(4-Flourobenzoyl)hydrazino]phenyl}-3-phenylthiourea.
Claim 60
Dependent Claim
1 words
1-{4-[2-(4-Flourobenzoyl)hydrazino]phenyl}-3-phenylthiourea.
Claim 61
Dependent Claim
1 words
1-{4-[2-(4-Methylbenzoyl)hydrazino]phenyl}-3-phenylthiourea.
Claim 62
Dependent Claim
1 words
1-{4-[2-(4-Methylbenzoyl)hydrazino]phenyl}-3-phenylthiourea.
Claim 63
Dependent Claim
1 words
1-{4-[2-(4-Methoxybenzoyl)hydrazino]-phenyl}-3-phenylthiourea.
Claim 64
Dependent Claim
1 words
1-{4-[2-(4-Methoxybenzoyl)hydrazino]-phenyl}-3-phenylthiourea.
Claim 65
Dependent Claim
1 words
1-{4-[2-(4-Chlorobenzoyl)hydrazino]phenyl}-3-benzylthiourea.
Claim 66
Dependent Claim
1 words
1-{4-[2-(4-Chlorobenzoyl)hydrazino]phenyl}-3-benzylthiourea.
Claim 67
Dependent Claim
1 words
1-{-4-[2-(4-Fluorobenzoyl)hydrazino]phenyl}-3-benzylthiourea.
Claim 68
Dependent Claim
1 words
1-{-4-[2-(4-Fluorobenzoyl)hydrazino]phenyl}-3-benzylthiourea.
Claim 69
Dependent Claim
1 words
1-[3-(2-Formylhydrazino)phenyl]-3-phenylthiourea.
Claim 70
Dependent Claim
1 words
1-[3-(2-Formylhydrazino)phenyl]-3-phenylthiourea.
Claim 71
Dependent Claim
1 words
1-[3-(2-Formylhydrazino)phenyl]-3-(4-methoxyphenyl)thiourea.
Claim 72
Dependent Claim
1 words
1-[3-(2-Formylhydrazino)phenyl]-3-(4-methoxyphenyl)thiourea.
Claim 73
Dependent Claim
1 words
1-[2-(2-Formylhydrazino)phenyl]-3-phenylthiourea.
Claim 74
Dependent Claim
1 words
1-[2-(2-Formylhydrazino)phenyl]-3-phenylthiourea.
Claim 75
Dependent Claim
49 words
A compound having the formula ##STR51## wherein R is a hydrogen, phenyl, 4-alkylphenyl, 4-halophenyl, 4-alkoxyphenyl, alkyl, cyclohexyl or phenylalkyl substituent; R 1 is para-phenylene or a 3 position alkyl, halo- or alkoxy substituted para-phenylene group; and said alkyl moieties in each instance include from 1 to 4 carbon atoms.
Claim 76
Dependent Claim
49 words
A compound having the formula ##STR51## wherein R is a hydrogen, phenyl, 4-alkylphenyl, 4-halophenyl, 4-alkoxyphenyl, alkyl, cyclohexyl or phenylalkyl substituent; R 1 is para-phenylene or a 3 position alkyl, halo- or alkoxy substituted para-phenylene group; and said alkyl moieties in each instance include from 1 to 4 carbon atoms.
Claim 77
Dependent Claim
1 words
1,3-Bis[4-(2-formylhydrazino)phenyl]thiourea.
Claim 78
Dependent Claim
1 words
1,3-Bis[4-(2-formylhydrazino)phenyl]thiourea.
Claim 79
Dependent Claim
1 words
1,3-Bis[4-(2-acetylhydrazino)phenyl]thiourea.
Claim 80
Dependent Claim
1 words
1,3-Bis[4-(2-acetylhydrazino)phenyl]thiourea.
Claim 81
Dependent Claim
1 words
1,3-Bis[4-(2-benzoylhydrazino)phenyl]thiourea.
Claim 82
Dependent Claim
1 words
1,3-Bis[4-(2-benzoylhydrazino)phenyl]thiourea.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-06-20 | 1980-12-20 | 1981-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-20 | 1984-12-20 | 1985-06-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-20 | 1988-12-20 | 1989-06-21 | $7700.00 | Window Closed / Lapsed |