CA2243836A1 - Composition comprising a complex of cyclodextrin with isothiazolinone in a water-soluble casing, and its use - Google Patents
Composition comprising a complex of cyclodextrin with isothiazolinone in a water-soluble casing, and its use Download PDFInfo
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- CA2243836A1 CA2243836A1 CA002243836A CA2243836A CA2243836A1 CA 2243836 A1 CA2243836 A1 CA 2243836A1 CA 002243836 A CA002243836 A CA 002243836A CA 2243836 A CA2243836 A CA 2243836A CA 2243836 A1 CA2243836 A1 CA 2243836A1
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- Prior art keywords
- complex
- water
- cyclodextrin
- composition
- isothiazolinone
- 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.)
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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
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
Abstract
A composition includes a complex of cyclodextrin with isothiazolinone in a water-soluble dust-proof casing. This composition is useful as a preservative in aqueous systems.
Description
BACKGROUND OF THE INVENTION
1. Field of the Invention The invention relates to a composition comprising a complex of cyclodextrin (CD) with isothiazolinone in a water-soluble casing, and its use as a preservative.
1. Field of the Invention The invention relates to a composition comprising a complex of cyclodextrin (CD) with isothiazolinone in a water-soluble casing, and its use as a preservative.
2. The Prior Art Due to microbes, products having an aqueous phase may have a tendency to produce odors, to discolorl to form gases or to change their consistency. By using preservatives, these undesirable influences can be prevented, slowed down or reduced.
Isothiazolinones are known effective preservatives.
They are commercially available as aqueous solutions and formulations in various concentrations, for example under the brand name Kathon~ of Rohm and Haas. A mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one in the ratio of 3:1 is commercially available, for examplel as Kathon~ CG as a 1.5% strength solution or as a 14% strength solution (Kathon~ LX).
-~ Isothiazolinones have many uses. For example, they are useful for the preservation of water-containing products and for the treatment of water in recirculating systems, such as cooling towers.
Cyclodextrins are cyclic oligosaccharides constructed from 6, 7 or 8 ~ 4)-linked anhydroglucose units. The ~
or y-cyclodextrins, which are prepared by enzymatic conversion of starch, differ in the diameter of their hydrophobic cavity and are generally suitable for the inclusion of a large number of lipophilic substances.
Complexes of cyclodextrins with isothiazolinones are known from the literature. Thus, CA: lO0: 156595 describes a ~-cyclodextrin complex of the sparingly soluble biocide 2-N-octyl-4-isothiazolin-3-one.
DE 43 13 408 describes an improved water solubility for biocides having a maximum solubility of 0.15 g/l in water by inclusion into cyclodextrins. The use of these biocides for the preservation of aqueous systems is also demonstrated.
However, the actual biocide concentrations obtained are not disclosed.
The complexation of isothiazolinones with ~-CD is known from CA:120:71552p. A reduced irritation of the skin was found for the complex of 4,5-dichloro-2-N-octyl-4-isothiazolin-3-one with ~-CD. The preparation of a solid complex of ~-cyclodextrin with 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one and its use as a bactericide, fungicide and agent for controlling slime is described.
Disadvantages of the disclosed solid complex are the possible formation of dust and the resulting exposure of skin and lungs to the toxic and caustic active compound.
US Patent No. 5,559,083 discloses a mixture of isothiazolinones and branched cyclodextrins ("branched CDs") for stabilizing the active compound in aqueous solution. A
disadvantage of the disclosed liquid formulation is the risk of spilling or spattering of the active compound concentrate.
Furthermore, a certain volume has to be measured for each application.
However, there is a serious risk of contaminating people due to improper use of these prior art formulations.
SUMMARY OF THE INVENTION
It is an object of the invention to provide a solid, dust-free formulation of isothiazolinones which can be easily measured and simply applied and which, therefore, does not create any risk to people.
The above object is achieved by a composition comprising a complex of cyclodextrin with isothiazolinone in a water-soluble dust-proof casing.
The isothiazoli.none is preferably selected from the group consisting of 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one and the mixtures thereof.
In the isothiazolinone/cyclodextrin complex, the composition according to the invention preferably contains 5-chloro-2-methyl-4-isothiazolin-3-one in an amount from 2% to 10%, by weight, and particularly preferably from 6% to 10%, by weight, based on the total weight of the complex.
In the isothiazolinone/cyclodextrin complex, the composition according to the invention preferably contains 2-methyl-4-isothiazolin-3-one in an amount from 0.1% to 3%, by weight, and particularly preferably from 0.5% to 1.5%, by weight, based on the total weight of the complex.
In the isothiazolinone/cyclodextrin complex, the composition according to the invention preferably contains a cyclodextrin selected from the group consisting of ~-CD, ~-CD
and the mixtures thereof. ~-CD is particularly preferred.
The isothiazolinone/cyclodextrin complexes which are present in the composition according to the invention are, if ~-cyclodextrin is used, prepared by a known process, for example in CA:120:71552p. However, the preparation can also be carried out as described, for example, in Example 1 of the present application. Corresponding complexes of isothiazolinone with y-CD can be prepared as described, for example, in Example 3 of the present application.
The isothiazolinone in the composition according to the invention is preferably a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one.
~ -CD, ~-CD or the mixtures thereof are particularly suitable for preparing the isothiazolinone/cyclodextrin complexes which are present in the composition according to the invention. ~-CD is especially preferred.
The water-soluble dust-proof casing comprises any dust-proof water-soluble materials. Preferred are casings or bags made of a film of water-soluble material or gelatin capsules. Particularly preferred are casings or bags made of a film of water-soluble polyvinyl alcohol.
The complex of isothiazolinones and cyclodextrins is preferably packaged in a water-soluble dust-proof casing in an effective amount required for the particular application.
Also, the complex may be packaged in an amount which simplifies the measurement of the composition of the invention. Packaging is carried out so that the isothiazolinone/cyclodextrin complex cannot escape from the sealed undamaged package.
Thus, the invention also relates to a process for preparing the composition of the invention, which comprises packaging an isothiazolinone/cyclodextrin complex prepared in a manner known per se in a defined amount in a water-soluble dust-proof casing.
Prior to packaging in a water-soluble dust-proof casing, the cyclodextrin complexes can, if required, be sieved, classified pneumatically, ground, tabletted, granulated or compacted in a known manner.
The composition of the invention is preferably used as a preservative. The invention, therefore, also relates to the use of the composition of the invention as a preservative and to preservatives containing the composition of the invention.
The composition of the invention can be used, for example, for the preservation of paints, coatings, adhesives, aqueous emulsions or dispersions, cooling lubricants, aqueous wash and cleaning baths, coagulation baths for coatings, cooling water, cosmetic products, water in air conditioning systems or for controlling slime in water recirculation systems in the paper and pulp industry. Hence, the composition of the invention is added to the material to be preserved. The invention, therefore, also relates to a method for preserving products having an aqueous phase, which comprises adding an effective preservative amount of a composition of the invention to the particular product having the aqueous phase.
An effective preservative amount of the complex or of the composition will produce an amount of the active ingredient isothiazolinone dissolved in the aqueous phase ranging from 15 to 30 ppm, and preferably from 18 to 29 ppm.
Other objects and features of the present invention will become apparent from the following detailed description considered in connection with the Examples which discloses several embodiments of the present invention. It should be understood, however, that the Examples are designed for the purpose of illustration only and not as a definition of the limits of the invention.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
Examples 1 to 3: Preparation of the cyclodextrin complexes:
Example 1:
500 g of ~-cyclodextrin (commercially available from Wacker-Chemie GmbH, Munich, under the name BETA W 7), 400 g of Kathon~ LX (10.3% of 5-chloro-2-methyl-4-isothiazolin-3-one, 3.7% of 2-methyl-4-isothiazolin-3-one, Rohm and Haas) and 1000 ml of water were heated to 90~C with stirring. After 60 minutes, the solution was cooled to room temperature with stirring and the resulting precipitate is filtered off, washed with 80 ml of water and dried in a drying chamber at 40~C. The active compound content was determined using HPLC.
Yield: 275 g of a slightly yellow solid having a content of 8.5% of 5-chloro-2-methyl-4-isothiazolin-3-one and 0.86% of 2-methyl-4-isothiazolin-3-one.
Example 2:
25 g of ~-cyclodextrin (Wacker-Chemie GmbH) and 20 g of Kathon~ LX were dissolved in 1000 ml of water. The solution was lyophilized. The active compound content was determined using HPLC.
Yield: 29 g of a loose-packed powder having a content of 6.3%
of 5-chloro-2-methyl-4-isothiazolin-3-one and 0.92~ of 2-methyl-4-isothiazolin-3-one.
Example 3:
287 g of ~-cyclodextrin (10% moisture, Wacker-Chemie GmbH "GAMMA W8") together with 500 ml of water and 200 g of Kathon~ LX were heated to 80~C. After 45 minutes, the mixture was cooled to 10~C with stirring and the precipitate was filtered off. The isolated cyclodextrin complex is dried in a desiccator over phosphorus pentoxide. The active compound content was determined using HPLC.
Yield: 311 g of a slightly yellow powder having a content of 7.2~ of 5-chloro-2-methyl-4-isothiazolin-3-one and 2.7% of 2-methyl-4-isothiazolin-3-one.
Examples 4 to 6: Packaging in a water-soluble casing:
g Example 4:
Two sheets of the dimensions 30 cm x 20 cm were cut from a water-soluble polyvinyl alcohol film and congruently placed on top of each other. The films were welded together on the two long sides and on one short side using a bag sealer.
100 g of the complex compound from Example 1 were filled into this open casing or bag, and the remaining side was then sealed.
Example 5:
A gelatin capsule having a volume capacity of 100 ml was filled with 25 g of the complex from Example 3. With gentle stirring, the gelatin capsule completely dissolves in 10 1 of water over a period of 45 minutes.
Example 6:
In a stirred tank, a cooling lubricant emulsion was prepared by mixing 3000 g of a fully synthetic cooling lubricant concentrate (EMOL-O-Grind 1195/1, May Lubrication) with 100 1 of deionized water. With gentle stirring, a flat polyvinyl alcohol bag of the dimensions 15 cm x 10 cm, which was filled with 35 g of the complex from Example 1, was added - to the cooling lubricant emulsion. After approximately 5 minutes, the bag had dissolved completely.
The 5-chloro-2-methyl-4-isothiazolin-3-one content was measured in time intervals using HPLC. The results are summarized in the table below.
Time 5-Chloro-2-methyl-4-isothiazolin-3-one content 15 minutes 18 ppm 30 minutes 26 ppm 60 minutes 29 ppm The resulting cooling lubricant emulsion exhibited excellent resistance against microbial attack.
While a few embodiments of the present invention have been described, it is to be understood that many changes and modifications may be made thereunto without departing from the spirit and scope of the invention as defined in the appended claims.
Isothiazolinones are known effective preservatives.
They are commercially available as aqueous solutions and formulations in various concentrations, for example under the brand name Kathon~ of Rohm and Haas. A mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one in the ratio of 3:1 is commercially available, for examplel as Kathon~ CG as a 1.5% strength solution or as a 14% strength solution (Kathon~ LX).
-~ Isothiazolinones have many uses. For example, they are useful for the preservation of water-containing products and for the treatment of water in recirculating systems, such as cooling towers.
Cyclodextrins are cyclic oligosaccharides constructed from 6, 7 or 8 ~ 4)-linked anhydroglucose units. The ~
or y-cyclodextrins, which are prepared by enzymatic conversion of starch, differ in the diameter of their hydrophobic cavity and are generally suitable for the inclusion of a large number of lipophilic substances.
Complexes of cyclodextrins with isothiazolinones are known from the literature. Thus, CA: lO0: 156595 describes a ~-cyclodextrin complex of the sparingly soluble biocide 2-N-octyl-4-isothiazolin-3-one.
DE 43 13 408 describes an improved water solubility for biocides having a maximum solubility of 0.15 g/l in water by inclusion into cyclodextrins. The use of these biocides for the preservation of aqueous systems is also demonstrated.
However, the actual biocide concentrations obtained are not disclosed.
The complexation of isothiazolinones with ~-CD is known from CA:120:71552p. A reduced irritation of the skin was found for the complex of 4,5-dichloro-2-N-octyl-4-isothiazolin-3-one with ~-CD. The preparation of a solid complex of ~-cyclodextrin with 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one and its use as a bactericide, fungicide and agent for controlling slime is described.
Disadvantages of the disclosed solid complex are the possible formation of dust and the resulting exposure of skin and lungs to the toxic and caustic active compound.
US Patent No. 5,559,083 discloses a mixture of isothiazolinones and branched cyclodextrins ("branched CDs") for stabilizing the active compound in aqueous solution. A
disadvantage of the disclosed liquid formulation is the risk of spilling or spattering of the active compound concentrate.
Furthermore, a certain volume has to be measured for each application.
However, there is a serious risk of contaminating people due to improper use of these prior art formulations.
SUMMARY OF THE INVENTION
It is an object of the invention to provide a solid, dust-free formulation of isothiazolinones which can be easily measured and simply applied and which, therefore, does not create any risk to people.
The above object is achieved by a composition comprising a complex of cyclodextrin with isothiazolinone in a water-soluble dust-proof casing.
The isothiazoli.none is preferably selected from the group consisting of 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one and the mixtures thereof.
In the isothiazolinone/cyclodextrin complex, the composition according to the invention preferably contains 5-chloro-2-methyl-4-isothiazolin-3-one in an amount from 2% to 10%, by weight, and particularly preferably from 6% to 10%, by weight, based on the total weight of the complex.
In the isothiazolinone/cyclodextrin complex, the composition according to the invention preferably contains 2-methyl-4-isothiazolin-3-one in an amount from 0.1% to 3%, by weight, and particularly preferably from 0.5% to 1.5%, by weight, based on the total weight of the complex.
In the isothiazolinone/cyclodextrin complex, the composition according to the invention preferably contains a cyclodextrin selected from the group consisting of ~-CD, ~-CD
and the mixtures thereof. ~-CD is particularly preferred.
The isothiazolinone/cyclodextrin complexes which are present in the composition according to the invention are, if ~-cyclodextrin is used, prepared by a known process, for example in CA:120:71552p. However, the preparation can also be carried out as described, for example, in Example 1 of the present application. Corresponding complexes of isothiazolinone with y-CD can be prepared as described, for example, in Example 3 of the present application.
The isothiazolinone in the composition according to the invention is preferably a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one.
~ -CD, ~-CD or the mixtures thereof are particularly suitable for preparing the isothiazolinone/cyclodextrin complexes which are present in the composition according to the invention. ~-CD is especially preferred.
The water-soluble dust-proof casing comprises any dust-proof water-soluble materials. Preferred are casings or bags made of a film of water-soluble material or gelatin capsules. Particularly preferred are casings or bags made of a film of water-soluble polyvinyl alcohol.
The complex of isothiazolinones and cyclodextrins is preferably packaged in a water-soluble dust-proof casing in an effective amount required for the particular application.
Also, the complex may be packaged in an amount which simplifies the measurement of the composition of the invention. Packaging is carried out so that the isothiazolinone/cyclodextrin complex cannot escape from the sealed undamaged package.
Thus, the invention also relates to a process for preparing the composition of the invention, which comprises packaging an isothiazolinone/cyclodextrin complex prepared in a manner known per se in a defined amount in a water-soluble dust-proof casing.
Prior to packaging in a water-soluble dust-proof casing, the cyclodextrin complexes can, if required, be sieved, classified pneumatically, ground, tabletted, granulated or compacted in a known manner.
The composition of the invention is preferably used as a preservative. The invention, therefore, also relates to the use of the composition of the invention as a preservative and to preservatives containing the composition of the invention.
The composition of the invention can be used, for example, for the preservation of paints, coatings, adhesives, aqueous emulsions or dispersions, cooling lubricants, aqueous wash and cleaning baths, coagulation baths for coatings, cooling water, cosmetic products, water in air conditioning systems or for controlling slime in water recirculation systems in the paper and pulp industry. Hence, the composition of the invention is added to the material to be preserved. The invention, therefore, also relates to a method for preserving products having an aqueous phase, which comprises adding an effective preservative amount of a composition of the invention to the particular product having the aqueous phase.
An effective preservative amount of the complex or of the composition will produce an amount of the active ingredient isothiazolinone dissolved in the aqueous phase ranging from 15 to 30 ppm, and preferably from 18 to 29 ppm.
Other objects and features of the present invention will become apparent from the following detailed description considered in connection with the Examples which discloses several embodiments of the present invention. It should be understood, however, that the Examples are designed for the purpose of illustration only and not as a definition of the limits of the invention.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
Examples 1 to 3: Preparation of the cyclodextrin complexes:
Example 1:
500 g of ~-cyclodextrin (commercially available from Wacker-Chemie GmbH, Munich, under the name BETA W 7), 400 g of Kathon~ LX (10.3% of 5-chloro-2-methyl-4-isothiazolin-3-one, 3.7% of 2-methyl-4-isothiazolin-3-one, Rohm and Haas) and 1000 ml of water were heated to 90~C with stirring. After 60 minutes, the solution was cooled to room temperature with stirring and the resulting precipitate is filtered off, washed with 80 ml of water and dried in a drying chamber at 40~C. The active compound content was determined using HPLC.
Yield: 275 g of a slightly yellow solid having a content of 8.5% of 5-chloro-2-methyl-4-isothiazolin-3-one and 0.86% of 2-methyl-4-isothiazolin-3-one.
Example 2:
25 g of ~-cyclodextrin (Wacker-Chemie GmbH) and 20 g of Kathon~ LX were dissolved in 1000 ml of water. The solution was lyophilized. The active compound content was determined using HPLC.
Yield: 29 g of a loose-packed powder having a content of 6.3%
of 5-chloro-2-methyl-4-isothiazolin-3-one and 0.92~ of 2-methyl-4-isothiazolin-3-one.
Example 3:
287 g of ~-cyclodextrin (10% moisture, Wacker-Chemie GmbH "GAMMA W8") together with 500 ml of water and 200 g of Kathon~ LX were heated to 80~C. After 45 minutes, the mixture was cooled to 10~C with stirring and the precipitate was filtered off. The isolated cyclodextrin complex is dried in a desiccator over phosphorus pentoxide. The active compound content was determined using HPLC.
Yield: 311 g of a slightly yellow powder having a content of 7.2~ of 5-chloro-2-methyl-4-isothiazolin-3-one and 2.7% of 2-methyl-4-isothiazolin-3-one.
Examples 4 to 6: Packaging in a water-soluble casing:
g Example 4:
Two sheets of the dimensions 30 cm x 20 cm were cut from a water-soluble polyvinyl alcohol film and congruently placed on top of each other. The films were welded together on the two long sides and on one short side using a bag sealer.
100 g of the complex compound from Example 1 were filled into this open casing or bag, and the remaining side was then sealed.
Example 5:
A gelatin capsule having a volume capacity of 100 ml was filled with 25 g of the complex from Example 3. With gentle stirring, the gelatin capsule completely dissolves in 10 1 of water over a period of 45 minutes.
Example 6:
In a stirred tank, a cooling lubricant emulsion was prepared by mixing 3000 g of a fully synthetic cooling lubricant concentrate (EMOL-O-Grind 1195/1, May Lubrication) with 100 1 of deionized water. With gentle stirring, a flat polyvinyl alcohol bag of the dimensions 15 cm x 10 cm, which was filled with 35 g of the complex from Example 1, was added - to the cooling lubricant emulsion. After approximately 5 minutes, the bag had dissolved completely.
The 5-chloro-2-methyl-4-isothiazolin-3-one content was measured in time intervals using HPLC. The results are summarized in the table below.
Time 5-Chloro-2-methyl-4-isothiazolin-3-one content 15 minutes 18 ppm 30 minutes 26 ppm 60 minutes 29 ppm The resulting cooling lubricant emulsion exhibited excellent resistance against microbial attack.
While a few embodiments of the present invention have been described, it is to be understood that many changes and modifications may be made thereunto without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (14)
1. A composition comprising a complex of cyclodextrin (CD) with isothiazolinone, and a water-soluble dust-proof casing containing said complex.
2. The composition as claimed in claim 1, wherein the isothiazolinone is selected from the group consisting of 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one and mixtures thereof.
3. The composition as claimed in claim 1, wherein the complex of cyclodextrin with isothiazolinone contains from 2%
to 10%, by weight, of 5-chloro-2-methyl-4-isothiazolin-3-one, based upon the total complex weight.
to 10%, by weight, of 5-chloro-2-methyl-4-isothiazolin-3-one, based upon the total complex weight.
4. The composition as claimed in claim 1, wherein the complex of cyclodextrin with isothiazolinone contains from 0.1%
to 3%, by weight, of 2-methyl-4-isothiazolin-3-one, based upon the total complex weight.
to 3%, by weight, of 2-methyl-4-isothiazolin-3-one, based upon the total complex weight.
5. The composition as claimed in claim 1, wherein the cyclodextrin is selected from the group consisting of .beta.-CD, .gamma.-CD and mixtures thereof.
6. The composition as claimed in claim 1, wherein the water-soluble dust-proof casing is selected from the group consisting of a film of water-soluble material and a gelatin capsule.
7. A process for preparing a composition comprising providing a water-soluble dust-proof casing; and packaging an effective amount of an isothiazolinone/cyclodextrin complex in said water-soluble dust-proof casing.
8. A method for preserving products having an aqueous phase, comprising the steps of providing a product having an aqueous phase; and adding an effective preservative amount of a complex of cyclodextrin with isothiazolinone in a water-soluble dust-proof casing to said product.
9. In a method for preserving a product, the improvement which comprises utilizing an effective preservative amount of a complex claimed in claim 1 for said preserving of the product.
10. A preservative comprising an effective preservative amount of a complex as claimed in claim 1.
11. The process as claimed in claim 7, wherein said effective amount of the complex ranges between 15 to 30 ppm.
12. The method as claimed in claim 8, wherein said effective amount of the complex ranges between 15 to 30 ppm.
13. The method as claimed in claim 9, wherein said effective amount of the complex ranges between 15 to 30 ppm.
14. The preservative as claimed in claim 10, wherein said effective amount of the complex ranges between 15 to 30 ppm.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19734244A DE19734244A1 (en) | 1997-08-07 | 1997-08-07 | A composition comprising a complex of cyclodextrin with isothiazolinone in a water-soluble shell and its use |
| DE19734244.2 | 1997-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2243836A1 true CA2243836A1 (en) | 1999-02-07 |
Family
ID=7838293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002243836A Abandoned CA2243836A1 (en) | 1997-08-07 | 1998-07-17 | Composition comprising a complex of cyclodextrin with isothiazolinone in a water-soluble casing, and its use |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0895718A3 (en) |
| JP (1) | JPH11116411A (en) |
| KR (1) | KR19990023419A (en) |
| CN (1) | CN1212836A (en) |
| BR (1) | BR9802858A (en) |
| CA (1) | CA2243836A1 (en) |
| DE (1) | DE19734244A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11180806A (en) * | 1997-12-22 | 1999-07-06 | Kurita Water Ind Ltd | Antimicrobial composition |
| DE19947182A1 (en) * | 1999-09-30 | 2001-05-03 | Wacker Chemie Gmbh | Wood preservatives, processes for their production and their use |
| EP1925201A1 (en) * | 2006-11-09 | 2008-05-28 | Werner Zapletal | Method for antimicrobial treatment of powder |
| JP5367304B2 (en) * | 2007-05-21 | 2013-12-11 | 丸三化学産業株式会社 | Microbicide packaging |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289815A (en) * | 1978-06-26 | 1981-09-15 | Airwick Industries, Inc. | Cold water-insoluble polyvinyl alcohol pouch for the controlled release of active ingredients |
| JPS57130914A (en) * | 1981-02-04 | 1982-08-13 | Agency Of Ind Science & Technol | Prolongation of activity retention |
| US4505889A (en) * | 1982-09-23 | 1985-03-19 | Rohm And Haas Company | Protracted release microbiocidal article for aqueous systems |
| JPH05247011A (en) * | 1992-03-04 | 1993-09-24 | Permachem Asia Ltd | Clathrate compound |
| DE4313408A1 (en) * | 1993-04-23 | 1994-10-27 | Boehringer Mannheim Gmbh | Cyclodextrin-biocid complex |
| US5559083A (en) * | 1994-04-04 | 1996-09-24 | Takeda Chemical Industries, Ltd. | Composition comprising an isothiazolone compound |
-
1997
- 1997-08-07 DE DE19734244A patent/DE19734244A1/en not_active Withdrawn
-
1998
- 1998-07-17 CA CA002243836A patent/CA2243836A1/en not_active Abandoned
- 1998-07-23 EP EP98113776A patent/EP0895718A3/en not_active Withdrawn
- 1998-08-06 KR KR1019980032056A patent/KR19990023419A/en not_active Application Discontinuation
- 1998-08-06 CN CN98117303A patent/CN1212836A/en active Pending
- 1998-08-06 BR BR9802858-8A patent/BR9802858A/en not_active IP Right Cessation
- 1998-08-07 JP JP10224352A patent/JPH11116411A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11116411A (en) | 1999-04-27 |
| CN1212836A (en) | 1999-04-07 |
| KR19990023419A (en) | 1999-03-25 |
| BR9802858A (en) | 2000-01-18 |
| DE19734244A1 (en) | 1999-02-11 |
| EP0895718A3 (en) | 1999-06-16 |
| EP0895718A2 (en) | 1999-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20020717 |