US4018611A
Expired / Lapsed
US
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Non-yellowing antimicrobial compositions comprising diiodomethyl sulfones
Assignee: Metalorgana Ets
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Filing: 1975-09-15
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Granted: 1977-04-19
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Expires: 1995-09-15
Abstract
Abstract There is provided an antimicrobial composition comprising a diiodomethyl sulfone of the formula R(CH 2 ) n SO 2 CHI 2 , wherein n is an integer from 0 to 4 and R is selected from the group alkyl, cycloalkyl, phenyl, naphthyl, loweralkylphenyl, polyloweralkylphenyl, lower-alkoxyphenyl, monohalophenyl, polyhalophenyl, haloloweralkylphenyl halonitrophenyl, nitrophenyl, nitroloweralkylphenyl, anilino, anilinophenyl, and anilamidophenyl and in order to prevent the yellowing and/or the discoloring of the diiodomethyl sulfone a compound containing a reactive sulfide or sulfhydryl group. If the compound containing a reactive sulfide or sulhydryl group is a dithiocarbamate the composition shows an increased antimicrobial activity. The method of protecting potential natural or industrial host materials against attack by micro-organisms, in particular bacteria, algae and fungi, comprising treating said host material with said diiodomethyl sulfone and with said compound containing a reactive sulfide or sulfhydryl group or incorporating said compounds therein is also disclosed.
Inventors
- 👤 Charles Robert Cramer
- 👤 Gerrit Dirk VANLenthe
- 👤 Dietmar Maier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 06:53
CPC Classifications
D; D06; D06M; D06M16/00; C; C09; C09D; C09D5/00; C09D5/14
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
96 words
In a method for protecting a host material against attack by micro-organisms comprising coating said host material with a diiodomethyl sulfone of the formula R(CH 2 ) n SO 2 CHI 2 , wherein n is an integer from 0 to 4 and R is selected from the group alkyl, cycloalkyl, phenyl, naphthyl, monoloweralkylphenyl, polyloweralkylphenyl, loweralkoxyphenyl, monohalophenyl, polyhalophenyl, haloloweralkylphenyl, halonitrophenyl, nitrophenyl, nitroloweralkylphenyl, anilino, anilinophenyl and anilamidophenyl, the improvement comprising admixing with said sulfone a sufficient amount of a compound containing a reactive sulfide or sulfhydryl group to prevent the changing in color of the diiodomethyl sulfone.
Claim 2
Dependent Claim
96 words
In a method for protecting a host material against attack by micro-organisms comprising coating said host material with a diiodomethyl sulfone of the formula R(CH 2 ) n SO 2 CHI 2 , wherein n is an integer from 0 to 4 and R is selected from the group alkyl, cycloalkyl, phenyl, naphthyl, monoloweralkylphenyl, polyloweralkylphenyl, loweralkoxyphenyl, monohalophenyl, polyhalophenyl, haloloweralkylphenyl, halonitrophenyl, nitrophenyl, nitroloweralkylphenyl, anilino, anilinophenyl and anilamidophenyl, the improvement comprising admixing with said sulfone a sufficient amount of a compound containing a reactive sulfide or sulfhydryl group to prevent the changing in color of the diiodomethyl sulfone.
Claim 3
Dependent Claim
62 words
The method of claim 1 wherein the compound containing a reactive sulfide or sulfhydryl group is represented by the general formula R 9 --S--X, wherein X is selected from the group consisting of hydrogen, R 9 --S-- and R 9 --, and R 9 is selected from the group consisting of hydrogen, an equivalent of a metal and an organic radical. pg,35
Claim 4
Dependent Claim
178 words
The method of claim 1 wherein the compound containing a reactive sulfide or sulfhydryl group is represented by the formula: ##STR6## wherein R 1 is selected from the group consisting of hydrogen and lower alkyl, R 2 is selected from the group consisting of hydrogen, lower alkyl, a residue of the general formula: ##STR7## wherein Alk represents an alkylene group having 1 to 6 carbon atoms and a residue of the formula: ##STR8## wherein R 6 is selected from the group consisting of hydrogen, loweralkyl and hydroxyloweralkyl and R 7 is selected from the group consisting of hydrogen, loweralkyl and hydroxyloweralkyl or wherein R 1 and R 2 together with the nitrogen atom to which they are attached form a heterocyclic ring having 4 to 6 carbon atoms, and R 3 is selected from the group consisting of hydrogen, an equivalent of a metal atom, a group R 8 --, R 8 CH 2 -- or R 8 --S--, wherein R 8 is an organic radical or wherein R 3 and R 7 together represent a methylene bridge.
Claim 5
Dependent Claim
22 words
The method of claim 3 where Alk represents an alkylene group having 2 to 3 carbon atoms and R 8 is: ##STR9##
Claim 6
Dependent Claim
18 words
The method of claim 1 wherein the compound containing a reactive sulfide or sulfhydryl group is a dithiocarbamate.
Claim 7
Dependent Claim
42 words
The method of claim 5 wherein the dithiocarbamate is an alkali metal, zinc or manganese salt of an N,N-diloweralkyldithiocarbamate or an alkali metal, zinc or manganese salt of an alkylene bis (dithiocarbamate) having 2 to 6 carbon atoms in the alkylene group.
Claim 8
Dependent Claim
50 words
The method of claim 5 wherein the dithiocarbamate is a compound of the formula: ##STR10## where R 1 is hydrogen or alkyl of 1 to 4 carbon atoms, R 2 is alkyl of 1 to 4 carbon atoms and R 3 is hydrogen, an alkali metal, zinc, manganese or hydrocarbyl.
Claim 9
Dependent Claim
17 words
The method of claim 1, wherein the compound containing a reactive sulfide or sulfhydryl group is zinc-N,N'-ethylenebis-(dithiocarbamate).
Claim 10
Dependent Claim
17 words
The method of claim 1, wherein the compound containing a reactive sulfide or sulfhydryl group is tetramethylthiuramdisulfide.
Claim 11
Dependent Claim
17 words
The method of claim 1, wherein the compound containing a reactive sulfide or sulfhydryl group is zinc-N,N'-propylene-1,2-bis-dithiocarbamate).
Claim 12
Dependent Claim
17 words
The method of claim 1, wherein the compound containing a reactive sulfide or sulfhydryl group is 3,5-dimethyl-1,3,5-2H-tetrahydrothiadiazine-2-thione.
Claim 13
Dependent Claim
17 words
The method of claim 1, wherein the compound containing a reactive sulfide or sulfhydryl group is zinc-N,N-dimethyldithiocarbamate.
Claim 14
Dependent Claim
91 words
In an antimicrobial composition adapted to protect a host material against attack by micro-organisms, said composition comprising a diiodomethyl sulfone of the formula R(CH 2 ) n SO 2 CHI 2 , wherein n is an integer from 0 to 4 and R is selected from the group alkyl, cycloalkyl, phenyl, naphthyl, monoloweralkylphenyl, polyloweralkylphenyl, loweralkoxyphenyl, monohalophenyl, polyhalophenyl, haloloweralkylphenyl, halonitrophenyl, nitrophenyl, nitroloweralkylphenyl, anilino, anilinophenyl and anilamidophenyl, the improvement comprising a sufficient amount of a compound containing a reactive sulfide or sulfhydryl group to prevent the changing in color of the diiodomethyl sulfone.
Claim 15
Dependent Claim
91 words
In an antimicrobial composition adapted to protect a host material against attack by micro-organisms, said composition comprising a diiodomethyl sulfone of the formula R(CH 2 ) n SO 2 CHI 2 , wherein n is an integer from 0 to 4 and R is selected from the group alkyl, cycloalkyl, phenyl, naphthyl, monoloweralkylphenyl, polyloweralkylphenyl, loweralkoxyphenyl, monohalophenyl, polyhalophenyl, haloloweralkylphenyl, halonitrophenyl, nitrophenyl, nitroloweralkylphenyl, anilino, anilinophenyl and anilamidophenyl, the improvement comprising a sufficient amount of a compound containing a reactive sulfide or sulfhydryl group to prevent the changing in color of the diiodomethyl sulfone.
Claim 16
Dependent Claim
60 words
The composition of claim 13 wherein the compound containing a reactive sulfide or sulfhydryl group is represented by the formula R 9 --S--X wherein X is selected from the group consisting of hydrogen, R 9 --S-- and R 9 --, and R 9 is selected from the group consisting of hydrogen, an equivalent of a metal and an organic radical.
Claim 17
Dependent Claim
181 words
The composition of claim 13 wherein the compound containing a reactive sulfide or sulfhydryl group is represented by the formula: ##STR11## wherein R 1 is selected from the group consisting of hydrogen and lower alkyl, R 2 is selected from the group consisting of hydrogen, lower alkyl, a residue of the general formula: ##STR12## where alk represents an alkylene group having 1 to 6 carbon atoms and a residue of the formula: ##STR13## wherein R 6 is selected from the group consisting of hydrogen lower alkyl and hydroxy lower alkyl and R 7 is selected from the group consisting of hydrogen, lower alkyl and hydroxy lower alkyl wherein R 1 and R 2 together with the nitrogen atom to which they are attached form a heterocyclic ring having 4 to 6 carbon atoms and R 3 is selected from the group consisting of hydrogen, an equivalent of a metal, a group R 8 --, R 8 CH 2 --or R 8 --S--, wherein R 8 is an organic radical, or wherein R 3 and R 7 together represent a methylene bridge.
Claim 18
Dependent Claim
22 words
The composition of claim 15 wherein Alk represents an alkylene group having 2 to 3 carbon atoms and R 8 is ##STR14##
Claim 19
Dependent Claim
11 words
The composition of claim 13 where n is 0 or 1.
Claim 20
Dependent Claim
18 words
The composition of claim 13 wherein the compound containing a reactive sulfide or sulfhydryl group is a dithiocarbamate.
Claim 21
Dependent Claim
45 words
The composition of claim 18 wherein the dithiocarbamate is an alkali metal, zinc or manganese salt of an N,N-di lower alkyl dithiocarbamate or an alkali metal, zinc or manganese salt of an alkylene bis (dithiocarbamate) having 2 to 6 carbon atoms in the alkylene group.
Claim 22
Dependent Claim
50 words
The composition of claim 18 wherein the dithiocarbamate is a compound of the formula: ##STR15## wherein R 1 is hydrogen or alkyl of 1 to 4 carbon atoms, R 2 is alkyl of 1 to 4 carbon atoms and R 3 is hydrogen, an alkali metal, zinc, manganese or hydrocarbyl.
Claim 23
Dependent Claim
10 words
The composition of claim 18 wherein the dithiocarbamate is tetramethylthiuramdisulfide.
Claim 24
Dependent Claim
10 words
The composition of claim 18 wherein the dithiocarbamate is zinc-N,N'-ethylene-bis-(dithiocarbamate).
Claim 25
Dependent Claim
10 words
The composition of claim 18 wherein the dithiocarbamate is zinc-N,N-propylene-1,2-bis-(dithiocarbamate).
Claim 26
Dependent Claim
10 words
The composition of claim 18 wherein the dithiocarbamate is 3,5-dimethyl-1,3,5-2H-tetrahydrothiadiazine-2-thione.
Claim 27
Dependent Claim
10 words
The composition of claim 18 wherein the dithiocarbamate is zinc-N,N-dimethyldithiocarbamate.
Claim 28
Dependent Claim
19 words
The composition of claim 13 wherein the compound containing a reactive sulfide or sulfhydryl group is an inorganic sulfide.
Claim 29
Dependent Claim
42 words
The composition of claim 13 wherein the compound containing a reactive sulfide or sulfhydryl group is present in a molar equivalent ratio of 1 mole diiodomethyl sulfone to 0.5 to 4 moles of the compound containing a reactive sulfide or sulfhydryl group.
Claim 30
Dependent Claim
31 words
The composition of claim 27 wherein the molar equivalent ratio is 1 mole of diiodomethyl sulfone to 1.8 to 2.4 moles of the compound containing a reactive sulfide or sulfhydryl group.
Claim 31
Dependent Claim
29 words
The composition of claim 28 wherein the molar equivalent ratio is 1 mole diiodomethyl sulfone to approximately 2 moles of the compound containing a reactive sulfide or sulfhydryl group.
Claim 32
Dependent Claim
37 words
The composition of claim 13 comprising from about 0.05 to 2% by weight of the total of the diiodomethyl sulfone and the compound containing a reactive sulfide or sulfhydryl group, the balance being a microbiocidally inert carrier.
Claim 33
Dependent Claim
22 words
The antimicrobial composition according to claim 30 suitable to protect a textile host from micri-organisms wherein the carrier is a volatile solvent.
Claim 34
Dependent Claim
13 words
The composition according to claim 30, wherein the carrier is a latex paint.
Claim 35
Dependent Claim
12 words
A composition according to claim 30 wherein the carrier is a plaster.
Claim 36
Dependent Claim
40 words
An industrial material comprising a potential host for attack by micro-organisms having at least a portion of its surface in contact with the antimicrobial composition according to claim 13 whereby said host is rendered resistant to attack by a micro-organism.
Claim 37
Dependent Claim
14 words
An industrial material according to claim 34, wherein the potential host is cotton fabric.
Claim 38
Dependent Claim
19 words
An industrial material according to claim 34 wherein the potential host is a paint film and its supporting substrate.
Claim 39
Dependent Claim
18 words
An industrial material according to claim 34, wherein the potential host is a plaster and its supporting substrate.
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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) | 1980-04-18 | 1980-10-18 | 1981-04-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-18 | 1984-10-18 | 1985-04-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-18 | 1988-10-18 | 1989-04-19 | $7700.00 | Window Closed / Lapsed |