EP3866600A1 - Stabile 1,2-benzisothiazolin-3-on enthaltende flüssige biozidzusammensetzungen - Google Patents
Stabile 1,2-benzisothiazolin-3-on enthaltende flüssige biozidzusammensetzungenInfo
- Publication number
- EP3866600A1 EP3866600A1 EP19789590.7A EP19789590A EP3866600A1 EP 3866600 A1 EP3866600 A1 EP 3866600A1 EP 19789590 A EP19789590 A EP 19789590A EP 3866600 A1 EP3866600 A1 EP 3866600A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- benzisothiazolin
- water
- biocide composition
- biocide
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 60
- 239000003139 biocide Substances 0.000 title claims abstract description 55
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000007788 liquid Substances 0.000 title claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- 235000013772 propylene glycol Nutrition 0.000 claims abstract description 16
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 13
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract description 13
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 13
- 239000011734 sodium Substances 0.000 claims abstract description 13
- -1 plasters Substances 0.000 claims abstract description 11
- 238000004140 cleaning Methods 0.000 claims abstract description 9
- 239000005068 cooling lubricant Substances 0.000 claims abstract description 8
- 239000006185 dispersion Substances 0.000 claims abstract description 8
- 239000000853 adhesive Substances 0.000 claims abstract description 6
- 230000001070 adhesive effect Effects 0.000 claims abstract description 6
- 239000010426 asphalt Substances 0.000 claims abstract description 6
- 239000000839 emulsion Substances 0.000 claims abstract description 6
- 239000010985 leather Substances 0.000 claims abstract description 6
- 239000003973 paint Substances 0.000 claims abstract description 6
- 239000000123 paper Substances 0.000 claims abstract description 6
- 239000004033 plastic Substances 0.000 claims abstract description 6
- 238000005498 polishing Methods 0.000 claims abstract description 6
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 238000004513 sizing Methods 0.000 claims abstract description 6
- 239000004094 surface-active agent Substances 0.000 claims abstract description 6
- 239000004753 textile Substances 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 4
- 238000000576 coating method Methods 0.000 claims abstract description 3
- 244000005700 microbiome Species 0.000 claims description 7
- 239000000565 sealant Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 239000008199 coating composition Substances 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 3
- 238000009987 spinning Methods 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007789 sealing Methods 0.000 abstract 1
- 229960004063 propylene glycol Drugs 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000003860 storage Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910003002 lithium salt Inorganic materials 0.000 description 5
- 159000000002 lithium salts Chemical class 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 230000003641 microbiacidal effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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
Definitions
- the invention relates to biocide compositions containing the components: (a) 15% by weight to 25% by weight of l, 2-benzisothiazolin-3-one in the form of its sodium and / or potassium salt, (b) 55 to 68% by weight. -% 1, 2-propanediol and (c) ad. 100% by weight water.
- the invention further relates to the use of these biocide compositions for the preservation of water-based products of all kinds, such as cleaning and household products, plastic dispersions, paints, plasters, adhesives, sealants, paper coating compositions, textile softeners and
- Sizing agents washing raw materials, surfactants, polishing agents, spinning baths, cooling lubricants, leather treatment agents and silicone and bitumen emulsions.
- the 1,2-benzisothiazolin-3-one (BIT) and its sodium, potassium and lithium salts have long been used in practice for the preparation of microbicidally active formulations.
- the active ingredient is characterized by good chemical and thermal stability and basically has a broad antimicrobial effect against bacteria, fungi and yeast.
- aqueous dispersions or solutions are produced from the raw BIT obtained in the synthesis.
- Such dispersions or solutions are not sufficiently stable in storage and settle over time.
- BIT in the form of its alkali salt dissolved in water contains certain hydroxyl-containing organic solvents, such as propylene glycol.
- US Pat. No. 4,871,754 discloses aqueous formulations of the lithium salt of 1,2-benzisothiazolin-3-one.
- these preparations are not sufficiently stable to cold at higher BIT concentrations and require the addition of a water-miscible organic solvent, such as 1,2 propylene glycol.
- the object of the invention was to provide alternative stable aqueous biocide compositions with a high content of 1,2-benzisothiazolin-3-one. It is also desirable that the compositions according to the invention should have a long shelf life even at low temperatures. This task is solved by a biocide composition containing the components:
- Benzisothiazolin-3-one in the form of its sodium and / or potassium salt (b) 55 to 68% by weight, preferably 58 to 66% by weight, particularly preferably 59 to
- the percentages by weight are based on the 1,2-benzisothiazolin-3-one, based on the 1,2-benzisothiazolin-3-one, that is to say on the active ingredient and not on the salts, and in relation to components (a), (b) and (c), each based on the total weight of the biocidal composition.
- new aqueous biocide compositions based on 1,2-benzisothiazolin-3-one, also referred to below as BIT have now been found within the scope of the present invention, which advantageously overcome the disadvantages of the prior art.
- the biocide compositions are characterized in particular by an advantageous viscosity and high storage and color stability. There is no significant degradation of the active ingredient during storage, nor are there any signs of clouding or filling during storage.
- the stable biocide compositions according to the invention preferably have a viscosity, measured according to Brookfield at 20 ° C. with spindle 1 at 30 rpm, of less than 120 mPas.
- stable or “storage-stable” mean that the biocide compositions deposit almost no solids on prolonged storage and preferably do not crystallize or solidify even at persistent temperatures of 0 ° C.
- the biocidal compositions according to the invention are characterized in that their pH is greater than or equal to pH 9, preferably in the range from pH 9 to pH 12, and particularly preferably in the range from pH 9.5 to pH 11.5.
- the biocide composition according to the invention contains 15% by weight to 25% by weight, preferably 18 to 22% by weight, of 1,2-benzisothiazolin-3-one in the form of its sodium and / or potassium salt, in each case based on the total weight of the biocide composition.
- the sodium and / or potassium salt of 1,2-benzisothiazolin-3-one can be prepared or formed, for example, by reacting 1,2-benzisothiazolin-3-one with sodium hydroxide and / or potassium hydroxide.
- the biocide composition according to the invention is characterized in that the molar proportion of the sodium salt of 1,2-benzisothiazolin-3-one, based on the total 1,2-benzisothiazolin-3-one salts, is at least 70 mol%. %, preferably at least 80 mol%, particularly preferably at least 90 mol%.
- the biocide composition according to the invention is characterized in that it contains the 1,2-benzisothiazolin-3-one in the form of its sodium salt.
- the biocide composition according to the invention contains 55 to 68% by weight, preferably 58 to 63% by weight, particularly preferably 59 to 61% by weight of 1,2-propanediol, in each case based on the total weight of the biocide composition.
- the 1,2-propanediol content based on the total weight of the biocide composition, should be at least 55% by weight, preferably at least 58% by weight, particularly preferably at least 59% by weight , so that the biocide compositions have the required properties.
- the biocide compositions according to the invention contain ad as component (c). 100% water. This means that in addition to components (a) and (b) and optionally other components such as thickeners, defoamers and dispersants, water is also present. Generally contain the biocide compositions according to the invention about 5 to 30 wt .-%, preferably about 8 to 27 wt .-% water, each based on the total weight of the biocide composition.
- a composition comprising exclusively components (a), (b) and (c) in the stated weight ratios, without the presence of another microbicidal active component, is referred to in the context of the present invention as "biocide composition according to the invention".
- the “biocide composition according to the invention” can have one or more further constituents in the stated weight ratios.
- the further constituent (s) can have a microbicidal action or they can have no microbicidal action , be about a solvent, dispersant or suspending agent.
- the "biocide composition according to the invention” consists of components (a), (b) and (c) in the mixing ratios indicated above (ie the biocide composition according to the invention). This means that the composition according to the invention contains only components (a), (b) and (c).
- the biocide composition according to the invention "essentially” consists of the components (a), (b) and (c) according to the invention, ie that one or more other biocides may also be present in addition to these, but these are contained in such an amount is present in which there is no contribution of the respective biocide other than the components of the microbicidal active components according to the invention to the overall effect of the resulting mixture.
- the invention further comprises a process for the preparation of the biocide compositions according to the invention, in which the individual components are mixed with one another with stirring at a temperature of 20 to 60 ° C.
- the stable biocide composition can be prepared in particular by the 1,2-benzisothiazolin-3-one, preferably in the form of a moist filter cake in the 1,2-propanediol, which may contain a small amount of water, with stirring at a temperature of about 20 to 60 ° C suspended. After that the potassium hydroxide and / or sodium hydroxide is added in the form of an aqueous solution. The mixture is then stirred at a temperature of about 20 to 60 ° C until the solid has dissolved. The biocide composition obtained can then optionally be filtered either warm, or after cooling to ambient conditions.
- the invention further relates to the use of the biocide compositions defined above for the preservation of water-containing or water-dilutable technical or products from infestation and / or destruction by microorganisms.
- Functional liquids and water-containing technical products which are susceptible to microbial attack can preferably be preserved with the compositions according to the invention.
- the use of the biocide compositions according to the invention is particularly suitable for the preservation of cleaning and household products, plastic dispersions, paints, plasters, adhesives, sealants, paper coating compositions, textile softeners and sizing agents, detergent raw materials, surfactants, polishing agents, spin baths, cooling lubricants, Leather treatment agents and silicone and bitumen emulsions.
- the biocide compositions according to the invention are particularly preferably suitable for the preservation of cooling lubricants, cleaning products and household products.
- the application concentrations of the composition to be used according to the invention depend on the type and the occurrence of the microorganisms to be controlled, the initial microbial load and the composition of the technical product or material to be protected.
- the optimum amount of use for a specific application can be determined in the laboratory by means of a series of tests.
- the application concentrations are in the range from 0.01 to 5% by weight, preferably from 0.05 to 1.0% by weight, of the biocide composition according to the invention, based on the technical product or material to be protected.
- the invention therefore also relates to a technical product containing water, selected from cleaning and household products, Plastic dispersions, paints, plasters, adhesives, sealants, paper coatings, textiles, plasticizers and sizing agents,
- Detergent raw materials, surfactants, polishing agents, spin baths, cooling lubricants, leather treatment agents and silicone and bitumen emulsions which has the biocidal composition defined above, preferably in an amount in the range from 0.01 to 5% by weight, preferably from 0.05 to 1.0% .-%, based on the technical product to be protected.
- the invention further relates to a method for controlling the growth of at least one microorganism in an aqueous liquid, comprising the step of adding a biocidal composition containing the components:
- the aqueous liquid is a cleaning or household product.
- the biocide composition contains the following components or consists of the following components:
- the biocide composition according to the invention comprises or consists of:
- the biocide composition according to the invention comprises or consists of:
- the biocide composition according to the invention comprises or consists of:
- biocide compositions with a 1,2-benzisothiazolin-3-one content of 20% by weight, the biocide compositions characterized in the table below were prepared and over a period of 14 days at room temperature, 2 ° C. or - 5 ° C, with inoculation twice every 7 days with crystals of the BIT salts contained.
- compositions of 1,2-benzisothiazolin-3-one which are stable in storage in the form of its sodium and / or potassium salt from a content of 1,2-propanediol of 55% by weight can be stored at lower temperatures. receive.
- composition was based on U.S. 4,871,754 using the lithium salt of 1,2-benzisothiazolin-3-one. As can be seen from these comparative examples, no storage-stable compositions can be obtained using the lithium salt.
- BIT 1, 2-benzisothiazolin-3-one
- PE phenoxyethanol
- PG 1, 2-propanediol
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP18000817 | 2018-10-18 | ||
PCT/EP2019/000291 WO2020078576A1 (de) | 2018-10-18 | 2019-10-09 | Stabile 1,2-benzisothiazolin-3-on enthaltende flüssige biozidzusammensetzungen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP3866600A1 true EP3866600A1 (de) | 2021-08-25 |
Family
ID=63965025
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19789590.7A Withdrawn EP3866600A1 (de) | 2018-10-18 | 2019-10-09 | Stabile 1,2-benzisothiazolin-3-on enthaltende flüssige biozidzusammensetzungen |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP3866600A1 (de) |
WO (1) | WO2020078576A1 (de) |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1191253A (en) | 1968-02-21 | 1970-05-13 | Ici Ltd | New Compositions of Matter |
ZA784934B (en) | 1977-09-30 | 1979-10-31 | Ici Ltd | Solutions of benzisothiazolinones |
DE3600271A1 (de) | 1986-01-08 | 1987-07-09 | Cassella Ag | Waessrige zubereitung von 1,2-benzisothiazolin-3-on |
EP2020178A1 (de) * | 2007-08-01 | 2009-02-04 | THOR GmbH | Biozide Zusammensetzung umfassend das Kaliumsalz des 1,2-Benzisothiazolin-3-ons und Ethylenglykol |
-
2019
- 2019-10-09 WO PCT/EP2019/000291 patent/WO2020078576A1/de unknown
- 2019-10-09 EP EP19789590.7A patent/EP3866600A1/de not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
WO2020078576A1 (de) | 2020-04-23 |
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