US4100163A
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Substituted 8-sulfonamidoquinolines
Assignee: General Mills Chemicals Inc
•
Filing: 1976-01-26
•
Granted: 1978-07-11
•
Expires: 1996-01-26
Abstract
Abstract Certain sulfonamidoquinolines and metal complexes thereof both of which are soluble in essentially water-immiscible organic solvents. The sulfonamidoquinolines have the structural formula <IMAGE> where the R, R1 and R2 groups and m and n are as defined in the specification and claims hereof. Solutions of the sulfonamidoquinolines and the metal complexes thereof in essentially water-immiscible organic solvents.
Inventors
- 👤 Michael J. Virnig
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 12:56
CPC Classifications
C; C01; C01G; C01G3/00; C01G3/003; C22; C22B; C22B3/00; C22B3/20; C22B3/26; C22B3/36; C22B3/362; C22B3/364; C01G11/00; C01G11/003; C01G13/00; C01G13/003; C01G21/00; C01G21/003; C01G5/00; C01G5/003; C01G51/00; C01G51/01; C01G53/00; C01G53/01; C01G9/00; C01G9/003; C07; C07C; C07C309/00; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/38; C07D215/40; C22B3/34; Y; Y02; Y02P; Y02P10/00; Y02P10/20
Claims Analysis
Total Claims: 119
Claim 1
Independent Claim
304 words
Compounds of the structure: ##STR41## where R is selected from the group consisting of alkyl and alkenyl of 8 to 20 carbon atoms and ##STR42## where R 3 is an alkylene of 1 to about 20 carbon atoms, p is 0 or 1, A is a monocyclic hydrocarbon ring or a bicyclic hydrocarbon ring wherein the ring or rings are 5 or 6 membered, q is a whole integer selected from 1, 2 and 3, r is 0 or 1, and q + r = 1 to 3, R 4 is an alkyl or alkenyl of up to about 20 carbon atoms such that the total number of carbon atoms in (R 4 ) q is at least 8 with the proviso that when q is 2 at least one R 4 contains 5 or more carbon atoms and when q is 2 or 3 and more than one of the R 4 groups are branched chain the branched chain groups are not on adjacent carbon atoms, R 5 is --Cl, --Br, --NO 2 or --O--R 6 wherein R 6 is a hydrocarbon group radical of from 1 to about 20 carbon atoms, n is 0, 1 or 2 with the proviso that when n is 2 the R 1 substituents are not on adjacent carbon atoms, m is 0 or 1 and R 1 and R 2 are selected from the group consisting of hydrocarbon groups of from 1 to 5 carbon atoms, --Cl, --Br, NO 2 and --O--R 6 , said compounds being further characterized as having solubilities of at least 2% by weight in an essentially water-immiscible, liquid hydrocarbon solvent having a flash point of at least 150° F and also further characterized in that the Cu++ complexes thereof have solubilities of at least 2% by weight in the said solvent.
Claim 2
Dependent Claim
304 words
Compounds of the structure: ##STR41## where R is selected from the group consisting of alkyl and alkenyl of 8 to 20 carbon atoms and ##STR42## where R 3 is an alkylene of 1 to about 20 carbon atoms, p is 0 or 1, A is a monocyclic hydrocarbon ring or a bicyclic hydrocarbon ring wherein the ring or rings are 5 or 6 membered, q is a whole integer selected from 1, 2 and 3, r is 0 or 1, and q + r = 1 to 3, R 4 is an alkyl or alkenyl of up to about 20 carbon atoms such that the total number of carbon atoms in (R 4 ) q is at least 8 with the proviso that when q is 2 at least one R 4 contains 5 or more carbon atoms and when q is 2 or 3 and more than one of the R 4 groups are branched chain the branched chain groups are not on adjacent carbon atoms, R 5 is --Cl, --Br, --NO 2 or --O--R 6 wherein R 6 is a hydrocarbon group radical of from 1 to about 20 carbon atoms, n is 0, 1 or 2 with the proviso that when n is 2 the R 1 substituents are not on adjacent carbon atoms, m is 0 or 1 and R 1 and R 2 are selected from the group consisting of hydrocarbon groups of from 1 to 5 carbon atoms, --Cl, --Br, NO 2 and --O--R 6 , said compounds being further characterized as having solubilities of at least 2% by weight in an essentially water-immiscible, liquid hydrocarbon solvent having a flash point of at least 150° F and also further characterized in that the Cu++ complexes thereof have solubilities of at least 2% by weight in the said solvent.
Claim 3
Dependent Claim
18 words
The compounds of claim 1 wherein R is an alkyl radical of 8 to about 20 carbon atoms.
Claim 4
Dependent Claim
10 words
The compounds of claim 2 wherein R is straight chained.
Claim 5
Dependent Claim
9 words
The compounds of claim 3 wherein R is n-octyl.
Claim 6
Dependent Claim
9 words
The compounds of claim 3 wherein R is n-hexadecyl.
Claim 7
Dependent Claim
10 words
The compounds of claim 2 wherein R is branched chain.
Claim 8
Dependent Claim
9 words
The compounds of claim 6 wherein R is 2-ethylhexyl.
Claim 9
Dependent Claim
9 words
The compounds of claim 6 wherein R is isodecyl.
Claim 10
Dependent Claim
11 words
The compounds of claim 2 wherein m and n are 0.
Claim 11
Dependent Claim
18 words
The compounds of claim 1 wherein R is an alkenyl radical of 8 to about 20 carbon atoms.
Claim 12
Dependent Claim
11 words
The compounds of claim 10 wherein m and n are 0.
Claim 13
Dependent Claim
9 words
The compounds of claim 1 wherein R is ##STR43##
Claim 14
Dependent Claim
9 words
The compounds of claim 12 wherein p is 1.
Claim 15
Dependent Claim
18 words
The compounds of claim 13 wherein R 3 is an alkylene radical of 1 or 2 carbon atoms.
Claim 16
Dependent Claim
14 words
The compounds of claim 14 wherein the ring or rings in A are 6-membered.
Claim 17
Dependent Claim
9 words
The compounds of claim 15 wherein A is phenyl.
Claim 18
Dependent Claim
12 words
The compounds of claim 16 wherein R 4 is an alkyl radical.
Claim 19
Dependent Claim
16 words
The compounds of claim 17 wherein one R 4 radical contains at least 8 carbon atoms.
Claim 20
Dependent Claim
19 words
The compounds of claim 18 wherein the R 4 radical containing at least 8 carbon atoms is branched chain.
Claim 21
Dependent Claim
16 words
The compounds of claim 19 wherein the branched chain alkyl radical is a linear alkylate group.
Claim 22
Dependent Claim
21 words
The compounds of claim 20 wherein R 3 is methylene, q is 1, r is 0 and R 4 is dodecyl.
Claim 23
Dependent Claim
11 words
The compounds of claim 13 wherein m and n are 0.
Claim 24
Dependent Claim
9 words
The compounds of claim 12 wherein p is 0.
Claim 25
Dependent Claim
9 words
The compounds of claim 23 wherein r is 0.
Claim 26
Dependent Claim
14 words
The compounds of claim 23 wherein the ring or rings in A are 6-membered.
Claim 27
Dependent Claim
9 words
The compounds of claim 25 wherein A is naphthyl.
Claim 28
Dependent Claim
9 words
The compounds of claim 25 wherein A is phenyl.
Claim 29
Dependent Claim
13 words
The compounds of claim 23 wherein q is 1 and A is phenyl.
Claim 30
Dependent Claim
11 words
The compounds of claim 28 wherein R 4 is straight chained.
Claim 31
Dependent Claim
10 words
The compounds of claim 29 wherein R 4 is n-hexadecyl.
Claim 32
Dependent Claim
9 words
The compounds of claim 29 wherein r is 0.
Claim 33
Dependent Claim
11 words
The compounds of claim 29 wherein m and n are 0.
Claim 34
Dependent Claim
11 words
The compounds of claim 28 wherein R 4 is branched chain.
Claim 35
Dependent Claim
10 words
The compounds of claim 33 wherein R 4 is dodecyl.
Claim 36
Dependent Claim
10 words
The compounds of claim 33 wherein R 4 is pentadecyl.
Claim 37
Dependent Claim
17 words
The compounds of claim 33 wherein the branched chain R 4 group is a linear alkyl group.
Claim 38
Dependent Claim
10 words
The compounds of claim 36 wherein R 4 is heptyl.
Claim 39
Dependent Claim
10 words
The compounds of claim 36 wherein R 4 is dodecyl.
Claim 40
Dependent Claim
10 words
The compounds of claim 36 wherein R 4 is hexadecyl.
Claim 41
Dependent Claim
12 words
The compounds of claim 33 wherein m, n and r are 0.
Claim 42
Dependent Claim
12 words
The compounds of claim 36 wherein m, n and r are 0.
Claim 43
Dependent Claim
15 words
The compounds of claim 36 wherein m is 1 and n and r are 0.
Claim 44
Dependent Claim
12 words
The compounds of claim 42 wherein R 2 is an alkyl group.
Claim 45
Dependent Claim
13 words
The compounds of claim 23 wherein q is 2 and A is phenyl.
Claim 46
Dependent Claim
28 words
The compounds of claim 44 wherein one of the R 4 groups contains 5 carbon atoms and the second R 4 group contains at least 5 carbon atoms.
Claim 47
Dependent Claim
18 words
The compounds of claim 44 wherein one of the R 4 groups contains at least 8 carbon atoms.
Claim 48
Dependent Claim
19 words
The compounds of claim 46 wherein the R 4 group containing at least 8 carbon atoms is branched chain.
Claim 49
Dependent Claim
13 words
The compounds of claim 47 wherein the second R 4 group is methyl.
Claim 50
Dependent Claim
13 words
The compounds of claim 47 wherein the second R 4 group is ethyl.
Claim 51
Dependent Claim
12 words
The compounds of claim 47 wherein the second alkyl group is isopropyl.
Claim 52
Dependent Claim
14 words
The compounds of claim 48 wherein the branched chain R 4 group is nonyl.
Claim 53
Dependent Claim
17 words
The compounds of claim 47 wherein the branched chain R 4 group is a linear alkylate group.
Claim 54
Dependent Claim
22 words
The compounds of claim 52 wherein the branched chain R 4 group is octyl and the second R 4 radical is methyl.
Claim 55
Dependent Claim
22 words
The compounds of claim 52 wherein the branched chain R 4 group is decyl and the second R 4 radical is methyl.
Claim 56
Dependent Claim
22 words
The compounds of claim 52 wherein the branched chain R 4 group is decyl and the second R 4 group is ethyl.
Claim 57
Dependent Claim
22 words
The compounds of claim 52 wherein the banched chain R 4 group is decyl and the second R 4 group is isopropyl.
Claim 58
Dependent Claim
22 words
The compounds of claim 52 wherein the branched chain R 4 group is dodecyl and the second R 4 group is methyl.
Claim 59
Dependent Claim
12 words
The compounds of claim 52 wherein m, n and r are 0.
Claim 60
Dependent Claim
15 words
The compounds of claim 52 wherein m is 1 and n and r are 0.
Claim 61
Dependent Claim
12 words
The compounds of claim 59 wherein R 2 is an alkyl group.
Claim 62
Dependent Claim
26 words
The compounds of claim 60 wherein R 2 is methyl, the branched chain R 4 group is decyl and the second R 4 group is methyl.
Claim 63
Dependent Claim
15 words
The compounds of claim 52 wherein n is 1 and m and r are 0.
Claim 64
Dependent Claim
22 words
The compounds of claim 62 wherein the branched chain R 4 group is decyl and the second R 4 group is methyl.
Claim 65
Dependent Claim
10 words
The compounds of claim 63 wherein R 1 is nitro.
Claim 66
Dependent Claim
10 words
The compounds of claim 63 wherein R 1 is methyl.
Claim 67
Dependent Claim
12 words
The compounds of claim 63 wherein R 1 is --O--R 6 .
Claim 68
Dependent Claim
10 words
The compounds of claim 66 wherein R 6 is methyl.
Claim 69
Dependent Claim
15 words
The compounds of claim 52 wherein n is 2 and m and r are 0.
Claim 70
Dependent Claim
26 words
The compounds of claim 68 wherein R 1 is Cl, the branched chain R 4 group is decyl and the second R 4 group is methyl.
Claim 71
Dependent Claim
13 words
The compounds of claim 23 wherein q is 2 and A is naphthyl.
Claim 72
Dependent Claim
20 words
The compounds of claim 70 wherein m, n and r are 0 and the R 4 groups are branched chain.
Claim 73
Dependent Claim
12 words
The compounds of claim 71 wherein the R 4 groups are nonyl.
Claim 74
Dependent Claim
13 words
The compounds of claim 23 wherein q is 3 and A is phenyl.
Claim 75
Dependent Claim
1 words
8-(2-Ethylhexanesulfonamido)quinoline.
Claim 76
Dependent Claim
1 words
8-(2-Ethylhexanesulfonamido)quinoline.
Claim 77
Dependent Claim
1 words
8-(n-Octanesulfonamido)quinoline.
Claim 78
Dependent Claim
1 words
8-(n-Octanesulfonamido)quinoline.
Claim 79
Dependent Claim
1 words
8-(n-Hexadecanesulfonamido)quinoline.
Claim 80
Dependent Claim
1 words
8-(n-Hexadecanesulfonamido)quinoline.
Claim 81
Dependent Claim
1 words
8-(Isodecanesulfonamido)quinoline.
Claim 82
Dependent Claim
1 words
8-(Isodecanesulfonamido)quinoline.
Claim 83
Dependent Claim
1 words
8-(Dodecylbenzenesulfonamido)quinoline.
Claim 84
Dependent Claim
1 words
8-(Dodecylbenzenesulfonamido)quinoline.
Claim 85
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)quinoline.
Claim 86
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)quinoline.
Claim 87
Dependent Claim
1 words
8-(Decylethylbenzenesulfonamido)quinoline.
Claim 88
Dependent Claim
1 words
8-(Decylethylbenzenesulfonamido)quinoline.
Claim 89
Dependent Claim
1 words
8-(Octylmethylbenzenesulfonamido)quinoline.
Claim 90
Dependent Claim
1 words
8-(Octylmethylbenzenesulfonamido)quinoline.
Claim 91
Dependent Claim
1 words
8-(Nonylmethylbenzenesulfonamido)quinoline.
Claim 92
Dependent Claim
1 words
8-(Nonylmethylbenzenesulfonamido)quinoline.
Claim 93
Dependent Claim
1 words
8-(Decylisopropylbenzenesulfonamido)quinoline.
Claim 94
Dependent Claim
1 words
8-(Decylisopropylbenzenesulfonamido)quinoline.
Claim 95
Dependent Claim
1 words
8-(Diamylbenzenesulfonamido)quinoline.
Claim 96
Dependent Claim
1 words
8-(Diamylbenzenesulfonamido)quinoline.
Claim 97
Dependent Claim
1 words
8-(Dinonylnaphthalenesulfonamido)quinoline.
Claim 98
Dependent Claim
1 words
8-(Dinonylnaphthalenesulfonamido)quinoline.
Claim 99
Dependent Claim
1 words
8-(Heptylbenzenesulfonamido)quinoline.
Claim 100
Dependent Claim
1 words
8-(Heptylbenzenesulfonamido)quinoline.
Claim 101
Dependent Claim
1 words
8-(Hexadecylbenzenesulfonamdio)quinoline.
Claim 102
Dependent Claim
1 words
8-(Hexadecylbenzenesulfonamdio)quinoline.
Claim 103
Dependent Claim
1 words
8-(2,4,6-Triisopropylbenzenesulfonamido)quinoline.
Claim 104
Dependent Claim
1 words
8-(2,4,6-Triisopropylbenzenesulfonamido)quinoline.
Claim 105
Dependent Claim
1 words
8-(Dodecylbenzenesulfonamido)-2-methylquinoline.
Claim 106
Dependent Claim
1 words
8-(Dodecylbenzenesulfonamido)-2-methylquinoline.
Claim 107
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-2-methylquinoline.
Claim 108
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-2-methylquinoline.
Claim 109
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-6-methylquinoline.
Claim 110
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-6-methylquinoline.
Claim 111
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-6-methoxyquinoline.
Claim 112
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-6-methoxyquinoline.
Claim 113
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-5-nitroquinoline.
Claim 114
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-5-nitroquinoline.
Claim 115
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-5,7-dichloroquinoline.
Claim 116
Dependent Claim
1 words
8-(Decylmethylbenzenesulfonamido)-5,7-dichloroquinoline.
Claim 117
Dependent Claim
1 words
8-(Dodecylphenylmethanesulfonamido)quinoline.
Claim 118
Dependent Claim
1 words
8-(Dodecylphenylmethanesulfonamido)quinoline.
Claim 119
Dependent Claim
55 words
The compounds of claim 1 which are further characterized as having solubilities of at least 2% by weight in a kerosene having a flash point of at least 150° F. and which are still further characterized in that the Cu++ complexes thereof also have solubilities of at least 2% by weight in the said kerosene.
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) | 1981-07-10 | 1982-01-09 | 1982-07-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-10 | 1986-01-09 | 1986-07-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-10 | 1990-01-09 | 1990-07-11 | $7700.00 | Window Closed / Lapsed |