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
- 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 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 239000007788 liquid Substances 0.000 title claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 230000006378 damage Effects 0.000 claims abstract description 6
- 239000006185 dispersion Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000853 adhesive Substances 0.000 claims abstract description 3
- 230000001070 adhesive effect Effects 0.000 claims abstract description 3
- 239000010426 asphalt Substances 0.000 claims abstract description 3
- 238000004140 cleaning Methods 0.000 claims abstract description 3
- 239000011248 coating agent Substances 0.000 claims abstract description 3
- 238000000576 coating method Methods 0.000 claims abstract description 3
- 239000003599 detergent Substances 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims abstract description 3
- 239000000839 emulsion Substances 0.000 claims abstract description 3
- 239000000314 lubricant Substances 0.000 claims abstract description 3
- 238000005498 polishing Methods 0.000 claims abstract description 3
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 3
- 238000004513 sizing Methods 0.000 claims abstract description 3
- 238000009987 spinning Methods 0.000 claims abstract description 3
- 229920002994 synthetic fiber Polymers 0.000 claims abstract description 3
- 239000010985 leather Substances 0.000 claims abstract 2
- 239000004014 plasticizer Substances 0.000 claims abstract 2
- 239000002994 raw material Substances 0.000 claims abstract 2
- 239000004753 textile Substances 0.000 claims abstract 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002334 glycols Chemical class 0.000 claims description 3
- 239000008139 complexing agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 13
- 239000000654 additive Substances 0.000 abstract description 10
- -1 amine compounds Chemical class 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- 241000222122 Candida albicans Species 0.000 description 3
- 241001136494 Talaromyces funiculosus Species 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 241000228245 Aspergillus niger Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- RVYQXTPUVCOSPF-UHFFFAOYSA-M sodium;2-(2,2-dihydroxyethylamino)acetate Chemical compound [Na+].OC(O)CNCC([O-])=O RVYQXTPUVCOSPF-UHFFFAOYSA-M 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 101001003194 Eleusine coracana Alpha-amylase/trypsin inhibitor Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 241000191967 Staphylococcus aureus 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
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-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
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4033272.1 | 1990-10-19 | ||
| DE19904033272 DE4033272C1 (enrdf_load_stackoverflow) | 1990-10-19 | 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 (enrdf_load_stackoverflow) |
| CA (1) | CA2053678A1 (enrdf_load_stackoverflow) |
| DE (1) | DE4033272C1 (enrdf_load_stackoverflow) |
| MX (1) | MX174315B (enrdf_load_stackoverflow) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4201038C2 (de) * | 1992-01-17 | 1996-03-28 | Schuelke & Mayr Gmbh | Desinfektionsmittelkonzentrat und Desinfektionsmittel auf Amin- und Alkoholbasis und deren Verwendung |
| GB9300936D0 (en) * | 1993-01-19 | 1993-03-10 | Zeneca Ltd | Stable liquid compositions and their use |
| DE4306344C1 (de) * | 1993-02-25 | 1994-08-04 | Schuelke & Mayr Gmbh | Desinfektionsmittelkonzentrat und Desinfektionsmittel auf Amin- und Alkoholbasis |
| DE19722757C5 (de) * | 1997-05-31 | 2010-01-21 | Bode Chemie Gmbh | Aldehydfreie Desinfektionsmittel für Flächen und Instrumente |
| EP1184507A1 (de) * | 2000-09-04 | 2002-03-06 | Sanitized Ag | Antimikrobielle Zusammensetzung enthaltend 1,2-Benzisothiazolin-3-on und ihre Verwendung für die Ausrüstung von Textilien |
| DE102005044855A1 (de) * | 2005-09-21 | 2007-03-29 | Clariant Produkte (Deutschland) Gmbh | Biozide Zusammensetzungen |
| DE102009048189A1 (de) | 2009-10-02 | 2011-04-07 | Schülke & Mayr GmbH | Lagerstabile mikrobizide Konzentrate und deren Verwendung als Konservierungsmittel |
| DE102009048188A1 (de) | 2009-10-02 | 2011-04-07 | Schülke & Mayr GmbH | Antimikrobiell wirksame Gebrauchslösungen enthaltend Kombinationen von Isothiazolonen und Aminen |
| PL2596702T3 (pl) * | 2011-11-25 | 2015-10-30 | Omya Int Ag | Sposób stabilizowania zawartości bakterii w wodnych preparatach mineralnych zawierających mielony, naturalny węglan wapnia i/lub strącony węglan wapnia, i/lub dolomit, i/lub poddany powierzchniowej reakcji węglan wapnia |
| US20160106099A1 (en) | 2013-05-28 | 2016-04-21 | Thor Gmbh | Microbicidal composition comprising isothiazolone and an amine oxide |
| WO2014191097A2 (en) | 2013-05-28 | 2014-12-04 | Thor Specialities (Uk) Limited | Microbicidal composition comprising an isothiazolone and an amineoxide |
| CN105792653A (zh) | 2013-11-19 | 2016-07-20 | 奥麒化工股份有限公司 | 增强了的防腐剂 |
| US10709129B2 (en) | 2016-12-22 | 2020-07-14 | Dupont Specialty Products Usa, Llc | Synergistic combination of bis-(3-aminopropyl)dodecylamine and sorbic acid |
| ES2991270T3 (es) | 2017-02-08 | 2024-12-03 | Vink Chemicals Gmbh & Co Kg | Composiciones microbicidas a base de derivados de 1,2-benzisotiazolin-3-ona |
| HUE053827T2 (hu) | 2017-05-03 | 2021-07-28 | Vink Chemicals Gmbh & Co Kg | Tárolás során stabil mikrobicid koncentrátumok és alkalmazásuk tartósítószerként |
| DE102019128548B3 (de) | 2019-10-22 | 2021-02-25 | Vink Chemicals Gmbh & Co. Kg | Verfahren zum ablösen von biofilmen |
| WO2022103729A1 (en) | 2020-11-10 | 2022-05-19 | Troy Technology Ii, Inc. | Bit compositions with significantly improved activity |
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 (de) * | 1980-03-11 | 1982-06-15 | Ci Co Me | Verfahren zur herstellung von desinfektionsformulierungen mit spezifischem wirkungsmechanismus. |
| DE3609939A1 (de) * | 1986-03-24 | 1987-10-01 | Cassella Ag | Fluessige zubereitung von 1,2-benzisothiazolin-3-on, ihre herstellung und verwendung |
| EP0385369B1 (de) * | 1989-02-27 | 1995-09-20 | Lonza Ag | Verfahren zur antimikrobiellen Konservierung von Tensiden |
| DE3911808A1 (de) * | 1989-04-11 | 1990-10-18 | Riedel De Haen Ag | Fluessiges konservierungsmittel |
-
1990
- 1990-10-19 DE DE19904033272 patent/DE4033272C1/de not_active Expired - Lifetime
-
1991
- 1991-09-06 EP EP19910115050 patent/EP0482328B1/de not_active Expired - Lifetime
- 1991-10-18 CA CA 2053678 patent/CA2053678A1/en not_active Abandoned
- 1991-10-18 MX MX9101671A patent/MX174315B/es not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MX174315B (es) | 1994-05-04 |
| DE4033272C1 (enrdf_load_stackoverflow) | 1991-10-10 |
| EP0482328A1 (de) | 1992-04-29 |
| EP0482328B1 (de) | 1995-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |