CA2053678A1 - Liquid 1,2-benzoisothiazoline-3-one preparation - Google Patents
Liquid 1,2-benzoisothiazoline-3-one preparationInfo
- Publication number
- CA2053678A1 CA2053678A1 CA 2053678 CA2053678A CA2053678A1 CA 2053678 A1 CA2053678 A1 CA 2053678A1 CA 2053678 CA2053678 CA 2053678 CA 2053678 A CA2053678 A CA 2053678A CA 2053678 A1 CA2053678 A1 CA 2053678A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- bit
- amines
- liquid composition
- accordance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
Abstract
Abstract The invention relates to a liquid preparation containing 1,2-benzoisothiazoline-3-one (BIT) and amines and optionally containing additional solvents and common additives, and containing as amine one or more amines having the general formula
Description
C~ ,c~
~6~ ?~
LI~ID 1.2-~NZOISOT~IAZO~I~E-~-ONE P~EP~RATI~
Field of the Invention The invention relates to a liquid preparation of 1,2-benzoisothiazoline-3-one (BIT) with an amine.
Back~round of the InY~n~lQ~
The 1,2-benzoisothiazoline-3-one (BIT) has been known as anti-microbially active substance and is used as preservative in technical applications or, in general, as an additive which is suitable to counteract material destruction ("Mikromatz", in german) caused by microbes.
To make this compound available in a convenient preparation that can be metered easily, an aqueous dispersion may be prepared with the crude BIT obtained during synthesis. Such dispersions, however, are not stable when stored and will settle in the course of time.
GB Patent 11 91 253 has disclosed aqueous solutions of crude BIT with two or more amine compounds of the series comprising the diethanol amine, triethanol amine, diisopropanol amine, triisopropanol amine or morpholine these aqueous solutions contain BIT in the form of a mixture of the amine salts. Furthermore, GB Patent 13 30 531 has disclosed that BIT amine salts can be imparted with better stability in a cold environment when they are ' present in the form of solutions in aliphatic, cycloaliphatic or heterocyclic amines having 2 to 60 C
atoms and do not have hydroxyl and ether groups. The effectiveness of these preparations against material destruction, however,frequently is not adequate.
Summ~y of the Invent;,o~
The present invention provides a liquid preparation of ~,2-benzoisothiazoline-3-one (BIT) and amines, and optionally with a content of additional solvents and common additives, characterized in that it contains, as an amine, one or more amines haviny the ~eneral formula . ~ , . . . - . :
.: . . ; : ~ .
, .. .
~' ~
~6~ ?~
LI~ID 1.2-~NZOISOT~IAZO~I~E-~-ONE P~EP~RATI~
Field of the Invention The invention relates to a liquid preparation of 1,2-benzoisothiazoline-3-one (BIT) with an amine.
Back~round of the InY~n~lQ~
The 1,2-benzoisothiazoline-3-one (BIT) has been known as anti-microbially active substance and is used as preservative in technical applications or, in general, as an additive which is suitable to counteract material destruction ("Mikromatz", in german) caused by microbes.
To make this compound available in a convenient preparation that can be metered easily, an aqueous dispersion may be prepared with the crude BIT obtained during synthesis. Such dispersions, however, are not stable when stored and will settle in the course of time.
GB Patent 11 91 253 has disclosed aqueous solutions of crude BIT with two or more amine compounds of the series comprising the diethanol amine, triethanol amine, diisopropanol amine, triisopropanol amine or morpholine these aqueous solutions contain BIT in the form of a mixture of the amine salts. Furthermore, GB Patent 13 30 531 has disclosed that BIT amine salts can be imparted with better stability in a cold environment when they are ' present in the form of solutions in aliphatic, cycloaliphatic or heterocyclic amines having 2 to 60 C
atoms and do not have hydroxyl and ether groups. The effectiveness of these preparations against material destruction, however,frequently is not adequate.
Summ~y of the Invent;,o~
The present invention provides a liquid preparation of ~,2-benzoisothiazoline-3-one (BIT) and amines, and optionally with a content of additional solvents and common additives, characterized in that it contains, as an amine, one or more amines haviny the ~eneral formula . ~ , . . . - . :
.: . . ; : ~ .
, .. .
~' ~
-2- ~ ~ , 3 ~ ? f.
(CH2 ) n ~ NH2 R-N <
(CH2)m-NH2 wherein R represents a straight-chained or branched alkyl or alkylene radical having 6 to 22 C atoms and n + m has a value of 4 to 12.
The invention provides new l:iquid preparations of BIT and amines which are stable on storage and exhibit a surprising synergistic effect against microbial destruction in technical applications in technical applications is suggested, in particular in technical products which contain water or can be diluted with water. The~ can be made into stable products with only water as solvent, and therefore are more suitable from the viewpoints of ecology, as well as human toxicology.
Detailed Description of the Invention The preparations of the invention herein may consist on one hand only of BIT and one or more amines having Formula I and not contain additional solvents. In ~; this case, the BIT content is restricted to a maximum of ;~ 10~ by weight to improve keeping and handling properties.
On the other hand, preparations with a higher BIT concentration and amines in accordance with Formula I
may be provided with one or more additional solvents.
~; Solvents which can be used, other than water are solvents which can be mixed with water such as low-molecular univalent, divalent and trivalent alcohols, glycols, di- and polyglycols, ether or glycols, di- and polyglycols such as ethanol, isopropanol, propanediol-l,3,glycerin, butanetriol-1,2,3,butanetriol-1,2,4,ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, dipropylene glycol, ethylene glyco]. monomethylether, ethylene glycol monoethylether, ethylene glycol monopropylether, ethylene glycol monobutylether, diethylene glycol monomethylether, , "~ : ~
diethyl glycol momoethylether, diethylene ~lycol monopropylether, diethylene glycol monobutylether, diethylene glycol dimethylether and diethylene glycol diethylether, whereby the use of dipropylene glycol and butyl digycol are preferred. Dihydroxyethylglycin sodium salt is also useful.
Li~uid preparations containing BIT and organic amines in accordance with Formula I and optionally other solvents should have a molecular ratio of BIT relative to the amines of at the most 3:1. With this concentration ratio, the entire BIT is converted into its amine salt.
In the case o-f an amine having Formula I, where R =
lauryl and m + n = 3, this means a ratio of 10 parts by weight of BIT to 6.6 parts by weight of amine. This weight ratio is attained in accordance with representative preparations 1 through 5 and 9 of following Table 1.
Useful organic amines having Formula I include those wherein R is C6- through C22- and, preferably C1o-through C1~-, straight-chained or branched alkyl or alkenyl amines such as, for example, derivatives of fatty amines R-NH2, where R represents a coconut fat alkyl-(Cg to C1g), (predominantly C12- to C1~- alkyl-), an oleyl (predominantly Clg-alkeny~ a stearyl-(C16- to C1g-alkyl-) or a tallow fatty alkyl radical (C16- to C1g-alkyl- or akenyl-). These products are commercially available and, as far as the length of the chain is concerned, can be used either having a broad or narrow C
atom distribution.
Particularly preferred are preparations where the amine compounds having Formula I have as substituent R a lauryl radial and n + m have a value of 3. Such amines are used preferably in an amount of 3 to 60%, together with approximately 5 to 35% by weight of BIT, in addition to the solvent, wherein the solvent consists essentially of ylycols and advantageously even of water, , . .
(CH2 ) n ~ NH2 R-N <
(CH2)m-NH2 wherein R represents a straight-chained or branched alkyl or alkylene radical having 6 to 22 C atoms and n + m has a value of 4 to 12.
The invention provides new l:iquid preparations of BIT and amines which are stable on storage and exhibit a surprising synergistic effect against microbial destruction in technical applications in technical applications is suggested, in particular in technical products which contain water or can be diluted with water. The~ can be made into stable products with only water as solvent, and therefore are more suitable from the viewpoints of ecology, as well as human toxicology.
Detailed Description of the Invention The preparations of the invention herein may consist on one hand only of BIT and one or more amines having Formula I and not contain additional solvents. In ~; this case, the BIT content is restricted to a maximum of ;~ 10~ by weight to improve keeping and handling properties.
On the other hand, preparations with a higher BIT concentration and amines in accordance with Formula I
may be provided with one or more additional solvents.
~; Solvents which can be used, other than water are solvents which can be mixed with water such as low-molecular univalent, divalent and trivalent alcohols, glycols, di- and polyglycols, ether or glycols, di- and polyglycols such as ethanol, isopropanol, propanediol-l,3,glycerin, butanetriol-1,2,3,butanetriol-1,2,4,ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, dipropylene glycol, ethylene glyco]. monomethylether, ethylene glycol monoethylether, ethylene glycol monopropylether, ethylene glycol monobutylether, diethylene glycol monomethylether, , "~ : ~
diethyl glycol momoethylether, diethylene ~lycol monopropylether, diethylene glycol monobutylether, diethylene glycol dimethylether and diethylene glycol diethylether, whereby the use of dipropylene glycol and butyl digycol are preferred. Dihydroxyethylglycin sodium salt is also useful.
Li~uid preparations containing BIT and organic amines in accordance with Formula I and optionally other solvents should have a molecular ratio of BIT relative to the amines of at the most 3:1. With this concentration ratio, the entire BIT is converted into its amine salt.
In the case o-f an amine having Formula I, where R =
lauryl and m + n = 3, this means a ratio of 10 parts by weight of BIT to 6.6 parts by weight of amine. This weight ratio is attained in accordance with representative preparations 1 through 5 and 9 of following Table 1.
Useful organic amines having Formula I include those wherein R is C6- through C22- and, preferably C1o-through C1~-, straight-chained or branched alkyl or alkenyl amines such as, for example, derivatives of fatty amines R-NH2, where R represents a coconut fat alkyl-(Cg to C1g), (predominantly C12- to C1~- alkyl-), an oleyl (predominantly Clg-alkeny~ a stearyl-(C16- to C1g-alkyl-) or a tallow fatty alkyl radical (C16- to C1g-alkyl- or akenyl-). These products are commercially available and, as far as the length of the chain is concerned, can be used either having a broad or narrow C
atom distribution.
Particularly preferred are preparations where the amine compounds having Formula I have as substituent R a lauryl radial and n + m have a value of 3. Such amines are used preferably in an amount of 3 to 60%, together with approximately 5 to 35% by weight of BIT, in addition to the solvent, wherein the solvent consists essentially of ylycols and advantageously even of water, , . .
3 e~ ~t`
including dilute (0.5% by weight) sodium hydroxide solutions. For example, such a composition may consist of 5 to 30% by weight of BIT, 3 to 20% by weight of an amine having Formula I, 25 to 4~% by weight of a glycol-containing solvent and 67 to 10% by weight of water.
In another embodiment, a preparation of the invention, in particular when producing low-emission preparations, may contain more or less organic solvents, whereby, in order to obtain preparations which are stable in a cold enviror~ent and when stored, the amine compound should be used in at least twice the amount necessary for BIT salt formation. For example, such a composition would then contain 5 to 20~ by weight of BIT and 6.5 to 26% by weight of the organic amine compound having Formula I and 88.5 to 54% by weight of water.
Other conventional additives may be nonionic, cationic and/or anionic surfactants used as emulsifying or dispersing agents or as solubilizers, whereby the amount of said additives is up to 25%, and preferably, 5 to 25% and, in particular 10 to 20%.
Additional additives may be known complexing agents and/or water-softening agents which are suitable for complexing calcium, magnesium or iron ions. The contents of these additives usually is below approximately 15% by weight and, preferably, not above 10% by weight, with respect to the preparation.
Furthermore, conventional additives may be color-imparting additives, aromatic substances, turbi~ity-providing substances and, of course, other disinfecting components.
The liquid preparation of the invention herein is suitable for use in industrial products which contain water or can be mixed with water and are used against destruction by microbes, in particular in liquid systems such as, for example, in the case of dispersions of synthetic materials using polystyrene, polyacrylate or , `' ~, '. ' ~'' polyvinyl acetate and further in dyes, adhesives, paper-coating materials, textile-plasticizing and sizing agents, in crucle detergents, cleaning and polishing agents, spinning baths, cold lubricants, leather-processing agents and in silicone and bitumen emulsions.
The inventive preparation is preferably used ina concentration of 0.05 to 0.3% by weight, with respect to the substrate to be preserved.
Apart from the principal inventive liquid : 10 preparation which, in the simplest case, consists of 10%
by weight of BIT and 90% by weight of the amine compound and represents a highly viscous clear solution which may be combined with additional additives, the ~ollowing Preparations of Table 1 provide more detailed information, whereby the concentration data relate to the :~ content of active ingredients. In order to prepare the liquid preparations of the invention, it is useful if the amine compound is first mixed with the solvents and any . optionally required auxiliary substances, followed by the addition of BIT and stirring at temperatures of 40 to 50 C until a clear solution is attained.
~.~
Pre~aration 1 Weiah~_%
1,2 benzoisothiazoline-3-one 35 ; lauryldiproplylenetriamine 23 dipropylene alycol 22 butyl digycol 20 Pre~ara~ion 2 1,2 benzoisothiazoline-3-one 10 lauryldiproplylenetriamine 6.6 dipropylene glycol 83.4 1,2 benzoisothiazoline-3-one 30 lauryldiproplylenetriamine 20 dipropylene glycol 38 water 12 , ~
Pre~axation 4 1,2 benzoisothiazoline-3-one 5 lauryldiproplylenetriamine 3.3 butyl digycol 50 1,2-propylene glycol 25 water 16.7 Pre~a~ation 5 1,2 benzoisothiazoline-3-one 10 lauryldiproplylenetriamine 6.6 dipropylene glycol 50 water 33.4 Pre~aration 6 1,2 benzoisothiazoline-3-one 10 lauryldiproplylenetriamine 13.2 water 76.8 Pre~ara~ion 7 1,2 benzoisothiazoline-3-one 18 lauryldiproplylenetriamine 35 water 47 Pre~aration 8 1,2 benzoisothiazoline-3-one 20 lauryldiproplylenetriamine 26 water 54 Pre~aratign 9 1,2 benzoisothiazoline-3-one 10 lauryldiproplylenetriamine 6.6 water 63.4 ethoxylated fatty alcohol with 11 EO 20 PreDaration 10 Benzisothiazolone 10 Laurylpropylidentriamine 18 Dihydroxyethylglycin sodium salt 20 5 Sodium hydroxide 0.5 Water to 100 The synergistic effectiveness increase achieved with the inventive preparations is obvious from the results of a dilution test series which was performed with a preparation of the invention and compared with the efEectiveness individual substances of that same preparation.
The test was carried out in accordance with the guidelines of the Deutsche Gesellschaft fur Hygiene und .
V'~' ',?j Mikrobiologie (German Association for Hygiene and Microbiology). The steps of dilution ranged from 5000, 2500, 1250 to 9.8 ~g/mL. The tested germs were:
Staphylococcus aureus ~Staph. aureus~
Pseu~omonas aeruginosa ~Ps. aeruginosa) Candida albicans (C. albicans) Penicillium funiculosum (P. funiculosum) Aspegillus niger (A. Niger) The minimum inhibiting concentrations (MIC
values) of Example A representing an inventive preparation, Examples B and C containing only the component benzoisothiazoline-3-one, and Example D
containing only the component lauryldipropylenetriamine were determined.
Inventive ~xample A was contained 10% of benzoisothiazoline-3-one, 10% of lauryldipropylenetriamine, 30% of dipropylene glycol and 50% of water.
Reference Example B in accordance with DE
Patent 2~ 40 273 contained 10% of benzoisothiazoline-3-one, 5.9% of sodium hydroxide solution (45%), 30% of dipropylene glycol and 54.1% of water.
Reference Example C in accordance with GB
Patent 11 92 253 contained 10% of benzoisothiazoline-3-one, 6.7% o~ ethylene diamine, 30% of dipropylene glycol and 53.3% of water.
Reference Example D contained 10% of lauryldipropylenetriamine, 30% of dipropylene glycol and 60% of water.
In order to demonstrate the synergism, the synergism index, (SI) was calculated in accordance with F. C. Kull, P. C. Eisman, H. D. Slverstrowicz and R. L.
Mayer, ~pplied Microbiology 9 (1961)538, according to the following formula:
' ' . ' . ~: . ; . ~
' - ---8 ~ " ;~
QA QB
~ _ = S :~
Qa Qb wherein Qa and Qb~ xespectively, represent the amount of components A and B alone, respectively; and QA and QB~
respectively, represent the amount of the respective component in a mixture of A and B which is required to arrive at a defined end point.
If SI < 1, a synergism exists: in the case of a SI = 1 a strictly additive effect is achieved; and a SI >
1 represents an antagonism.
At the end point of this dilution test series that concentration must be set which just barely still inhibits the growth of the micro-organisms, i.e., minimum inhibiting concentration (MIC).
Therefore, in order to calculate the SI values, the MIC values of the tested exarnples can be related to each other.
MIC Example ~ MIC Example SI
MIC Examples B or C MIC Example D
The SI values listed in the table below illustrate the presence of a synergism. It is particularly distinct in the case of the germs Ps.
aeruginosa and A. niger which are particularly relevant in practical applications. The result compared with known BIT formulations oEfers a more balanced spectrum of efficacy with lower concentrations of active components.
30 Germ ~X~ MIC Values ~g/ml]
A B C D SI
Staph. aureus 78 312 312 625 0.38 ; Ps. aeruginosa 312 2500 2500 2500 0.25 C. albicans 156 312 312 5000 0.53 P. funiculosum 78 156 156 5000 0.52 A. niger 312 1250 1250 5000 0.31 : . . : .
, . ' . .
- . : . . . .
_ 9 _ ~J ~
The invention has been described in detail with particular reference to certain preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.
~ .
including dilute (0.5% by weight) sodium hydroxide solutions. For example, such a composition may consist of 5 to 30% by weight of BIT, 3 to 20% by weight of an amine having Formula I, 25 to 4~% by weight of a glycol-containing solvent and 67 to 10% by weight of water.
In another embodiment, a preparation of the invention, in particular when producing low-emission preparations, may contain more or less organic solvents, whereby, in order to obtain preparations which are stable in a cold enviror~ent and when stored, the amine compound should be used in at least twice the amount necessary for BIT salt formation. For example, such a composition would then contain 5 to 20~ by weight of BIT and 6.5 to 26% by weight of the organic amine compound having Formula I and 88.5 to 54% by weight of water.
Other conventional additives may be nonionic, cationic and/or anionic surfactants used as emulsifying or dispersing agents or as solubilizers, whereby the amount of said additives is up to 25%, and preferably, 5 to 25% and, in particular 10 to 20%.
Additional additives may be known complexing agents and/or water-softening agents which are suitable for complexing calcium, magnesium or iron ions. The contents of these additives usually is below approximately 15% by weight and, preferably, not above 10% by weight, with respect to the preparation.
Furthermore, conventional additives may be color-imparting additives, aromatic substances, turbi~ity-providing substances and, of course, other disinfecting components.
The liquid preparation of the invention herein is suitable for use in industrial products which contain water or can be mixed with water and are used against destruction by microbes, in particular in liquid systems such as, for example, in the case of dispersions of synthetic materials using polystyrene, polyacrylate or , `' ~, '. ' ~'' polyvinyl acetate and further in dyes, adhesives, paper-coating materials, textile-plasticizing and sizing agents, in crucle detergents, cleaning and polishing agents, spinning baths, cold lubricants, leather-processing agents and in silicone and bitumen emulsions.
The inventive preparation is preferably used ina concentration of 0.05 to 0.3% by weight, with respect to the substrate to be preserved.
Apart from the principal inventive liquid : 10 preparation which, in the simplest case, consists of 10%
by weight of BIT and 90% by weight of the amine compound and represents a highly viscous clear solution which may be combined with additional additives, the ~ollowing Preparations of Table 1 provide more detailed information, whereby the concentration data relate to the :~ content of active ingredients. In order to prepare the liquid preparations of the invention, it is useful if the amine compound is first mixed with the solvents and any . optionally required auxiliary substances, followed by the addition of BIT and stirring at temperatures of 40 to 50 C until a clear solution is attained.
~.~
Pre~aration 1 Weiah~_%
1,2 benzoisothiazoline-3-one 35 ; lauryldiproplylenetriamine 23 dipropylene alycol 22 butyl digycol 20 Pre~ara~ion 2 1,2 benzoisothiazoline-3-one 10 lauryldiproplylenetriamine 6.6 dipropylene glycol 83.4 1,2 benzoisothiazoline-3-one 30 lauryldiproplylenetriamine 20 dipropylene glycol 38 water 12 , ~
Pre~axation 4 1,2 benzoisothiazoline-3-one 5 lauryldiproplylenetriamine 3.3 butyl digycol 50 1,2-propylene glycol 25 water 16.7 Pre~a~ation 5 1,2 benzoisothiazoline-3-one 10 lauryldiproplylenetriamine 6.6 dipropylene glycol 50 water 33.4 Pre~aration 6 1,2 benzoisothiazoline-3-one 10 lauryldiproplylenetriamine 13.2 water 76.8 Pre~ara~ion 7 1,2 benzoisothiazoline-3-one 18 lauryldiproplylenetriamine 35 water 47 Pre~aration 8 1,2 benzoisothiazoline-3-one 20 lauryldiproplylenetriamine 26 water 54 Pre~aratign 9 1,2 benzoisothiazoline-3-one 10 lauryldiproplylenetriamine 6.6 water 63.4 ethoxylated fatty alcohol with 11 EO 20 PreDaration 10 Benzisothiazolone 10 Laurylpropylidentriamine 18 Dihydroxyethylglycin sodium salt 20 5 Sodium hydroxide 0.5 Water to 100 The synergistic effectiveness increase achieved with the inventive preparations is obvious from the results of a dilution test series which was performed with a preparation of the invention and compared with the efEectiveness individual substances of that same preparation.
The test was carried out in accordance with the guidelines of the Deutsche Gesellschaft fur Hygiene und .
V'~' ',?j Mikrobiologie (German Association for Hygiene and Microbiology). The steps of dilution ranged from 5000, 2500, 1250 to 9.8 ~g/mL. The tested germs were:
Staphylococcus aureus ~Staph. aureus~
Pseu~omonas aeruginosa ~Ps. aeruginosa) Candida albicans (C. albicans) Penicillium funiculosum (P. funiculosum) Aspegillus niger (A. Niger) The minimum inhibiting concentrations (MIC
values) of Example A representing an inventive preparation, Examples B and C containing only the component benzoisothiazoline-3-one, and Example D
containing only the component lauryldipropylenetriamine were determined.
Inventive ~xample A was contained 10% of benzoisothiazoline-3-one, 10% of lauryldipropylenetriamine, 30% of dipropylene glycol and 50% of water.
Reference Example B in accordance with DE
Patent 2~ 40 273 contained 10% of benzoisothiazoline-3-one, 5.9% of sodium hydroxide solution (45%), 30% of dipropylene glycol and 54.1% of water.
Reference Example C in accordance with GB
Patent 11 92 253 contained 10% of benzoisothiazoline-3-one, 6.7% o~ ethylene diamine, 30% of dipropylene glycol and 53.3% of water.
Reference Example D contained 10% of lauryldipropylenetriamine, 30% of dipropylene glycol and 60% of water.
In order to demonstrate the synergism, the synergism index, (SI) was calculated in accordance with F. C. Kull, P. C. Eisman, H. D. Slverstrowicz and R. L.
Mayer, ~pplied Microbiology 9 (1961)538, according to the following formula:
' ' . ' . ~: . ; . ~
' - ---8 ~ " ;~
QA QB
~ _ = S :~
Qa Qb wherein Qa and Qb~ xespectively, represent the amount of components A and B alone, respectively; and QA and QB~
respectively, represent the amount of the respective component in a mixture of A and B which is required to arrive at a defined end point.
If SI < 1, a synergism exists: in the case of a SI = 1 a strictly additive effect is achieved; and a SI >
1 represents an antagonism.
At the end point of this dilution test series that concentration must be set which just barely still inhibits the growth of the micro-organisms, i.e., minimum inhibiting concentration (MIC).
Therefore, in order to calculate the SI values, the MIC values of the tested exarnples can be related to each other.
MIC Example ~ MIC Example SI
MIC Examples B or C MIC Example D
The SI values listed in the table below illustrate the presence of a synergism. It is particularly distinct in the case of the germs Ps.
aeruginosa and A. niger which are particularly relevant in practical applications. The result compared with known BIT formulations oEfers a more balanced spectrum of efficacy with lower concentrations of active components.
30 Germ ~X~ MIC Values ~g/ml]
A B C D SI
Staph. aureus 78 312 312 625 0.38 ; Ps. aeruginosa 312 2500 2500 2500 0.25 C. albicans 156 312 312 5000 0.53 P. funiculosum 78 156 156 5000 0.52 A. niger 312 1250 1250 5000 0.31 : . . : .
, . ' . .
- . : . . . .
_ 9 _ ~J ~
The invention has been described in detail with particular reference to certain preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.
~ .
Claims (9)
1. Liquid preparation of 1,2-benzoisothiazoline-3-one (BIT) and amines characterized in that it contains one or more amines having the general formula wherein R represents a straight-chained or branched alkyl or alkylene radical having 6 to 22 C atoms and n + m has a value of 4 to 12.
2. Liquid composition in accordance with Claim 1, characterized in that it contains an amine having the general Formula I, wherein the radical R has 10 to 14 C atoms.
3. Liquid composition in accordance with Claims 1 or 2, characterized in that it contains an amine having the general Formula I, wherein n + m has a value of 6.
4. Liquid composition in accordance with Claim 1 or 2, characterized in that it consists of 10% by weight of BIT and at least 90% by weight of amines having Formula I.
5. Liquid composition in accordance with Claims 1 or 2, characterized in that it contains BIT and amines having Formula I in a molecular ration of at the most 3:1.
6. Liquid composition in accordance with Claim 1 characterized in that it contains 10% by weight of BIT and18% by weight of laurylpropylidentriamine.
7. Liquid composition in accordance with Claim 1 or 2, characterized in that it contains 5 to 35%
by weight of BIT, up to 95% by weight of amines having Formula I, and a diluent of the group comprising glycol ether, glycols and water.
by weight of BIT, up to 95% by weight of amines having Formula I, and a diluent of the group comprising glycol ether, glycols and water.
8. Liquid composition in accordance with Claim 1 or 2, characterized in that it contains 20% by weight of a complexing agent.
9. Use of a liquid composition in an amount of at least 0.05 to 0.3% (by weight) in products, which contain water or are diluted with water such as dispersions of synthetic materials, dyes, adhesives, paper-coating materials, textile plasticizers, sizing agents, raw materials for detergents, cleaning and polishing agents, spinning baths, cold lubricants, leather treatment agents, and silicone and bitumen emulsions, as agent against material destruction caused by microbes.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904033272 DE4033272C1 (en) | 1990-10-19 | 1990-10-19 | |
| DEP4033272.1 | 1990-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2053678A1 true CA2053678A1 (en) | 1992-04-20 |
Family
ID=6416655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2053678 Abandoned CA2053678A1 (en) | 1990-10-19 | 1991-10-18 | Liquid 1,2-benzoisothiazoline-3-one preparation |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0482328B1 (en) |
| CA (1) | CA2053678A1 (en) |
| DE (1) | DE4033272C1 (en) |
| MX (1) | MX174315B (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4201038C2 (en) * | 1992-01-17 | 1996-03-28 | Schuelke & Mayr Gmbh | Disinfectant concentrate and amine and alcohol based disinfectants and their use |
| GB9300936D0 (en) * | 1993-01-19 | 1993-03-10 | Zeneca Ltd | Stable liquid compositions and their use |
| DE4306344C1 (en) * | 1993-02-25 | 1994-08-04 | Schuelke & Mayr Gmbh | Disinfectant concentrate and amine and alcohol based disinfectants |
| DE19722757C5 (en) * | 1997-05-31 | 2010-01-21 | Bode Chemie Gmbh | Aldehyde-free disinfectant for surfaces and instruments |
| EP1184507A1 (en) * | 2000-09-04 | 2002-03-06 | Sanitized Ag | Antimicrobial composition comprising 1,2-Benzisothiazolin-3-one and use thereof in textile finishing |
| DE102005044855A1 (en) * | 2005-09-21 | 2007-03-29 | Clariant Produkte (Deutschland) Gmbh | Biocidal compositions |
| DE102009048188A1 (en) | 2009-10-02 | 2011-04-07 | Schülke & Mayr GmbH | Antimicrobially effective use solutions containing combinations of isothiazolones and amines |
| DE102009048189A1 (en) | 2009-10-02 | 2011-04-07 | Schülke & Mayr GmbH | Storage-stable microbicidal concentrates and their use as preservatives |
| PT2596702E (en) * | 2011-11-25 | 2015-09-21 | Omya Int Ag | Process for stabilizing bacterial content of aqueous ground natural calcium carbonate and/or precipitated calcium carbonate and/or dolomite and/or surface-reacted calcium carbonate-comprising mineral preparations |
| EP3003035A2 (en) | 2013-05-28 | 2016-04-13 | Thor Specialities (UK) Limited | Microbicidal composition comprising an isothiazolone and an amineoxide |
| EP3003040A1 (en) | 2013-05-28 | 2016-04-13 | THOR GmbH | Microbicidal composition comprising 2-methyl-4-isothiazolin-3-one and an amineoxide |
| WO2015077209A1 (en) * | 2013-11-19 | 2015-05-28 | Arch Chemicals, Inc. | Enhanced preservative |
| EP3557994B1 (en) * | 2016-12-22 | 2020-12-23 | Dow Global Technologies LLC | Synergistic combination of bis-(3-aminopropyl)dodecylamine and sorbic acid |
| EP3360413A1 (en) | 2017-02-08 | 2018-08-15 | Schülke & Mayr GmbH | New preservative composition based on 1,2-benzisothiazolin-3-one |
| PL3398436T3 (en) | 2017-05-03 | 2021-08-30 | Vink Chemicals Gmbh & Co. Kg | Storage-stable microbicidal concentrates and use thereof as preservatives |
| DE102019128548B3 (en) | 2019-10-22 | 2021-02-25 | Vink Chemicals Gmbh & Co. Kg | PROCESS FOR RELEASING BIOFILMENTS |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1330531A (en) * | 1970-03-31 | 1973-09-19 | Ici Ltd | 1,2-benzisothiazolone solutions |
| CH630227A5 (en) * | 1980-03-11 | 1982-06-15 | Ci Co Me | METHOD FOR PRODUCING DISINFECTIVE FORMULATIONS WITH SPECIFIC EFFECTIVE MECHANISM. |
| DE3609939A1 (en) * | 1986-03-24 | 1987-10-01 | Cassella Ag | LIQUID PREPARATION OF 1,2-BENZISOTHIAZOLIN-3-ON, ITS PRODUCTION AND USE |
| ES2076980T3 (en) * | 1989-02-27 | 1995-11-16 | Lonza Ag | PROCEDURE FOR THE ANTIMICROBIAL CONSERVATION OF SURFACE AGENTS. |
| DE3911808A1 (en) * | 1989-04-11 | 1990-10-18 | Riedel De Haen Ag | LIQUID PRESERVATIVE |
-
1990
- 1990-10-19 DE DE19904033272 patent/DE4033272C1/de not_active Expired - Lifetime
-
1991
- 1991-09-06 EP EP19910115050 patent/EP0482328B1/en not_active Expired - Lifetime
- 1991-10-18 CA CA 2053678 patent/CA2053678A1/en not_active Abandoned
- 1991-10-18 MX MX9101671A patent/MX174315B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0482328A1 (en) | 1992-04-29 |
| DE4033272C1 (en) | 1991-10-10 |
| EP0482328B1 (en) | 1995-12-20 |
| MX174315B (en) | 1994-05-04 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Dead |