CA2670201C - Controlled foam aqueous quaternary ammonium and phosphonium compositions - Google Patents
Controlled foam aqueous quaternary ammonium and phosphonium compositions Download PDFInfo
- Publication number
- CA2670201C CA2670201C CA2670201A CA2670201A CA2670201C CA 2670201 C CA2670201 C CA 2670201C CA 2670201 A CA2670201 A CA 2670201A CA 2670201 A CA2670201 A CA 2670201A CA 2670201 C CA2670201 C CA 2670201C
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- Prior art keywords
- quaternary ammonium
- compound
- branched
- linear
- alkyl
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- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 title claims description 35
- 239000006260 foam Substances 0.000 title claims description 32
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 title claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 26
- 230000003115 biocidal effect Effects 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000003643 water by type Substances 0.000 claims abstract description 8
- -1 phosphonium compound Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 27
- 238000009472 formulation Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 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 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 159000000007 calcium salts Chemical class 0.000 claims description 7
- 239000011591 potassium Substances 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- SOSQXPIKTBUEKF-UHFFFAOYSA-N 1,4-dihexoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound CCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCC SOSQXPIKTBUEKF-UHFFFAOYSA-N 0.000 claims description 4
- 241000195493 Cryptophyta Species 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 4
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000498 cooling water Substances 0.000 claims description 4
- 229960000878 docusate sodium Drugs 0.000 claims description 4
- 230000002147 killing effect Effects 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 4
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- CBCQTCPKFYFJEU-UHFFFAOYSA-N 1,4-dioxo-1,4-dipentoxybutane-2-sulfonic acid Chemical compound CCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCC CBCQTCPKFYFJEU-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003139 biocide Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 3
- 229910052698 phosphorus Chemical group 0.000 claims description 3
- 239000011574 phosphorus Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- ICAXUQIEOXHXKK-UHFFFAOYSA-N 1,4-dioxo-1,4-di(tridecoxy)butane-2-sulfonic acid Chemical compound CCCCCCCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCCCCCCC ICAXUQIEOXHXKK-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000005690 diesters Chemical group 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 239000002351 wastewater Substances 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 239000003171 wood protecting agent Substances 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
- 229940125797 compound 12 Drugs 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000005187 foaming Methods 0.000 abstract description 9
- 150000004714 phosphonium salts Chemical class 0.000 abstract description 5
- 239000003619 algicide Substances 0.000 abstract description 3
- 230000002829 reductive effect Effects 0.000 abstract description 3
- 230000009182 swimming Effects 0.000 abstract description 3
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 20
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 235000010216 calcium carbonate Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 101100288310 Arabidopsis thaliana KTI2 gene Proteins 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- RZMWTGFSAMRLQH-UHFFFAOYSA-L disodium;2,2-dihexyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCC RZMWTGFSAMRLQH-UHFFFAOYSA-L 0.000 description 2
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- JMHWNJGXUIJPKG-UHFFFAOYSA-N CC(=O)O[SiH](CC=C)OC(C)=O Chemical compound CC(=O)O[SiH](CC=C)OC(C)=O JMHWNJGXUIJPKG-UHFFFAOYSA-N 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
- 241000700605 Viruses Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YWQIGRBJQMNGSN-UHFFFAOYSA-M sodium;1,4-dioxo-1,4-di(tridecoxy)butane-2-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCOC(=O)CC(S([O-])(=O)=O)C(=O)OCCCCCCCCCCCCC YWQIGRBJQMNGSN-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- AKUNSPZHHSNFFX-UHFFFAOYSA-M tributyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC AKUNSPZHHSNFFX-UHFFFAOYSA-M 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
- B01D19/0422—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing S-atoms
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
- A61L2/08—Radiation
- A61L2/10—Ultraviolet radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/18—Liquid substances or solutions comprising solids or dissolved gases
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
- B01D19/0413—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing N-atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/65—Mixtures of anionic with cationic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0026—Low foaming or foam regulating compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/02—Non-contaminated water, e.g. for industrial water supply
- C02F2103/023—Water in cooling circuits
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/26—Nature of the water, waste water, sewage or sludge to be treated from the processing of plants or parts thereof
- C02F2103/28—Nature of the water, waste water, sewage or sludge to be treated from the processing of plants or parts thereof from the paper or cellulose industry
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/42—Nature of the water, waste water, sewage or sludge to be treated from bathing facilities, e.g. swimming pools
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2303/00—Specific treatment goals
- C02F2303/04—Disinfection
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2303/00—Specific treatment goals
- C02F2303/12—Prevention of foaming
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2305/00—Use of specific compounds during water treatment
- C02F2305/04—Surfactants, used as part of a formulation or alone
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/60—Sulfonium or phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dispersion Chemistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The foaming tendency of aqueous systems containing biocidal quaternary ammonium and/or phosphonium compounds is reduced by addition of anionic surfactants in a molar ratio of anionic surfactant(s) to quaternary compound(s) of from 0.001 to 0.2. A preferred application of the aqueous systems according to the invention is in swimming pool or spa waters as algaecides.
Description
Controlled Foam Aqueous Quaternary Ammonium and Phosphonium Compositions FIELD OF THE INVENTION
This invention relates to a method for controlling foam formation in aqueous systems containing biocidal quaternary ammonium and/or phosphonium compounds ("quats").
This invention also relates to low foam aqueous formulations comprising quaternary ammonium and/or phosphonium compounds and the use of said formulations compounds in a method for killing or inhibiting the growth of microorganisms, algae and fungi.
BACKGROUND OF THE INVENTION
Several quaternary ammonium and phosphonium compounds ("quats") exhibit marked biocidal activity and, consequently, have been used as active ingredients in disinfectants, preservatives, or other compositions for killing or controlling the growth of microorganisms, such as bacteria or viruses, as well as algae and fungi for many years.
However, since many of those quats have also surfactant properties, their use in aqueous systems is often impaired by intensive foaming even at low quat concentrations in the ppm range, which is particularly detrimental in applications where aqueous systems are agitated while being exposed to the atmosphere, such as swimming pool or spa waters or waters in cooling towers.
SUMMARY OF THE INVENTION
Applicants have found that the addition of at least one anionic surfactant to an aqueous system containing at least one biocidal quaternary ammonium and/or phosphonium compound in an amount corresponding to a molar ratio of anionic surfactant to quaternary ammonium and/or phosphonium compound of from 0.001 to 0.2 (i.e., 0.001:1 to 0.2:1), preferably from 0.001 to 0.09, substantially reduces the volume and lifetime of foam formed during the use of the aqueous system.
As anionic surfactants are known to decrease the biocidal efficacy of quaternary ammonium compounds, the observed foam reduction achieved by addition of anionic surfactants at much less than a molar equivalency is important from the quat performance perspective. Since only small amounts of e.g. 0.1 or 0.02 molar equivalents of anionic surfactant are required, the compositions retain about 90 or 98 percent, respectively, of their active quat concentrations.
In a more preferred embodiment, the molar ratio of anionic surfactant to quaternary ammonium and/or phosphonium compound is from 0.001 to 0.05.
This invention relates to a method for controlling foam formation in aqueous systems containing biocidal quaternary ammonium and/or phosphonium compounds ("quats").
This invention also relates to low foam aqueous formulations comprising quaternary ammonium and/or phosphonium compounds and the use of said formulations compounds in a method for killing or inhibiting the growth of microorganisms, algae and fungi.
BACKGROUND OF THE INVENTION
Several quaternary ammonium and phosphonium compounds ("quats") exhibit marked biocidal activity and, consequently, have been used as active ingredients in disinfectants, preservatives, or other compositions for killing or controlling the growth of microorganisms, such as bacteria or viruses, as well as algae and fungi for many years.
However, since many of those quats have also surfactant properties, their use in aqueous systems is often impaired by intensive foaming even at low quat concentrations in the ppm range, which is particularly detrimental in applications where aqueous systems are agitated while being exposed to the atmosphere, such as swimming pool or spa waters or waters in cooling towers.
SUMMARY OF THE INVENTION
Applicants have found that the addition of at least one anionic surfactant to an aqueous system containing at least one biocidal quaternary ammonium and/or phosphonium compound in an amount corresponding to a molar ratio of anionic surfactant to quaternary ammonium and/or phosphonium compound of from 0.001 to 0.2 (i.e., 0.001:1 to 0.2:1), preferably from 0.001 to 0.09, substantially reduces the volume and lifetime of foam formed during the use of the aqueous system.
As anionic surfactants are known to decrease the biocidal efficacy of quaternary ammonium compounds, the observed foam reduction achieved by addition of anionic surfactants at much less than a molar equivalency is important from the quat performance perspective. Since only small amounts of e.g. 0.1 or 0.02 molar equivalents of anionic surfactant are required, the compositions retain about 90 or 98 percent, respectively, of their active quat concentrations.
In a more preferred embodiment, the molar ratio of anionic surfactant to quaternary ammonium and/or phosphonium compound is from 0.001 to 0.05.
2 Preferably, the at least one quaternary ammonium and/or phosphonium compound is selected from (1) a compound having the formula [QR1R2R3R4] X- (I), wherein Q is nitrogen or phosphorus, R1 and R2 are independently unsubstituted or hydroxy-substituted linear or branched C1-4 alkyl; -(CH2CH20)mCH2CH2OH, or -(CH2CH(CH3)0)111CH2CH(CH3)0H, where m in each molecule independently is an integer from 1 to 10;
R3 is an optionally substituted benzyl, ethylbenzyl, naphthylmethyl, or linear or branched C6-22 alkyl group;
R4 is an optionally substituted benzyl, ethylbenzyl, methylnaphthyl, or linear or branched C1-22 alkyl group or -R5(0)1,(C6H4)R6, wherein n is 0 or 1;
R5 is substituted or unsubstituted C1-8 alkanediyl or -(CH2)p-0-(CH2)q-wherein p and q independently are integers from 1 to 8;
R6 is hydrogen or a substituted or unsubstituted, linear or branched C1-12 alkyl group; and X- is a monovalent or one equivalent of a polyvalent anion;
(ii) a compound having the formula Ri9R20R21R22Q+ --A (II), wherein Q is nitrogen or 20, -=-.21, phosphorus, R19, R and R22 are independently linear, branched, cyclic or any combination thereof saturated or unsaturated hydrocarbyl groups, X- is a monovalent or one equivalent of a polyvalent anion, and the sum of the carbon atoms numbers of R19, R20, -21 K and R22 ranges from 10 to 50;
(iii) a polymeric quaternary ammonium or phosphonium biocide; and (iv) a mixture of two or more quaternary compounds of any of (i) to (iii).
More preferably, the quaternary ammonium and/or phosphonium compound has the formula [QR1R2R3R4J4 X- (I), wherein Q is as defined above, both R1 and R2 are alkyl, R3 is a linear or branched C6-22 alkyl, R4 is benzyl or a linear or branched C1-22 alkyl and X- is chloride.
=
R3 is an optionally substituted benzyl, ethylbenzyl, naphthylmethyl, or linear or branched C6-22 alkyl group;
R4 is an optionally substituted benzyl, ethylbenzyl, methylnaphthyl, or linear or branched C1-22 alkyl group or -R5(0)1,(C6H4)R6, wherein n is 0 or 1;
R5 is substituted or unsubstituted C1-8 alkanediyl or -(CH2)p-0-(CH2)q-wherein p and q independently are integers from 1 to 8;
R6 is hydrogen or a substituted or unsubstituted, linear or branched C1-12 alkyl group; and X- is a monovalent or one equivalent of a polyvalent anion;
(ii) a compound having the formula Ri9R20R21R22Q+ --A (II), wherein Q is nitrogen or 20, -=-.21, phosphorus, R19, R and R22 are independently linear, branched, cyclic or any combination thereof saturated or unsaturated hydrocarbyl groups, X- is a monovalent or one equivalent of a polyvalent anion, and the sum of the carbon atoms numbers of R19, R20, -21 K and R22 ranges from 10 to 50;
(iii) a polymeric quaternary ammonium or phosphonium biocide; and (iv) a mixture of two or more quaternary compounds of any of (i) to (iii).
More preferably, the quaternary ammonium and/or phosphonium compound has the formula [QR1R2R3R4J4 X- (I), wherein Q is as defined above, both R1 and R2 are alkyl, R3 is a linear or branched C6-22 alkyl, R4 is benzyl or a linear or branched C1-22 alkyl and X- is chloride.
=
3 Still more preferably, the quaternary ammonium and/or phosphonium compound has the formula [QRIR2R3R4]+ X- (I), wherein Q is as defined above, both RI and R2 are methyl, R3 is a linear or branched C6-22 alkyl, R4 is benzyl or a linear or branched C6-22 alkyl and X- is chloride.
Most preferably, Q is nitrogen.
Particularly preferred are ammonium and phosphonium compounds such as alkyldimethyl-benzylammonium chloride or tributyl-tetradecylphosphonium chloride.
In another preferred embodiment, X- in formula (I) and/or (II) is selected from the group consisting of Y2CO3-, HCO3and OH-.
In still another preferred embodiment the at least one anionic surfactant is a sulfonate.
In another preferred embodiment the at least one anionic surfactant is a diester.
In a particularly preferred embodiment, the at least one anionic surfactant is selected from the group consisting of diamyl sulfosuccinate, dihexyl sulfosuccinate, dioctyl sulfosuccinate, ditridecyl sulfosuccinate, the potassium, sodium and calcium salts of any of the foregoing and any mixture of any of the foregoing sulfosuccinates and salts.
In one most preferred embodiment, the at least one anionic surfactant is selected from the group consisting of dihexyl sulfosuccinate and the potassium, sodium and calcium salts thereof sulfonate.
In another most preferred embodiment, the at least one anionic surfactant is selected from the group consisting of dioctyl sulfosuccinate and the potassium, sodium and calcium salts thereof In still another most preferred embodiment, the at least one anionic surfactant is selected from the group consisting of diamyl sulfosuccinate and the potassium, sodium and calcium salts thereof.
Of the above sulfosuccinate salts, the sodium salts are particularly preferred.
The above sulfonates have been observed to substantially reduce foaming while maintaining a high level of quat activity.
Preferably, the aqueous system contains from 0.1 to 100 ppm, more preferably from 0.5 to 50 ppm, of the biocidal quaternary ammonium and/or phosphonium compound.
Most preferably, Q is nitrogen.
Particularly preferred are ammonium and phosphonium compounds such as alkyldimethyl-benzylammonium chloride or tributyl-tetradecylphosphonium chloride.
In another preferred embodiment, X- in formula (I) and/or (II) is selected from the group consisting of Y2CO3-, HCO3and OH-.
In still another preferred embodiment the at least one anionic surfactant is a sulfonate.
In another preferred embodiment the at least one anionic surfactant is a diester.
In a particularly preferred embodiment, the at least one anionic surfactant is selected from the group consisting of diamyl sulfosuccinate, dihexyl sulfosuccinate, dioctyl sulfosuccinate, ditridecyl sulfosuccinate, the potassium, sodium and calcium salts of any of the foregoing and any mixture of any of the foregoing sulfosuccinates and salts.
In one most preferred embodiment, the at least one anionic surfactant is selected from the group consisting of dihexyl sulfosuccinate and the potassium, sodium and calcium salts thereof sulfonate.
In another most preferred embodiment, the at least one anionic surfactant is selected from the group consisting of dioctyl sulfosuccinate and the potassium, sodium and calcium salts thereof In still another most preferred embodiment, the at least one anionic surfactant is selected from the group consisting of diamyl sulfosuccinate and the potassium, sodium and calcium salts thereof.
Of the above sulfosuccinate salts, the sodium salts are particularly preferred.
The above sulfonates have been observed to substantially reduce foaming while maintaining a high level of quat activity.
Preferably, the aqueous system contains from 0.1 to 100 ppm, more preferably from 0.5 to 50 ppm, of the biocidal quaternary ammonium and/or phosphonium compound.
4 Another object of the invention is a low foam formulation comprising at least one biocidal quaternary ammonium and/or phosphonium compound and at least one anionic surfactant, wherein the molar ratio of anionic surfactant(s) to quaternary ammonium and/or phosphonium compound(s) is from 0.001 to 0.2, preferably from 0.001 to 0.09 and more preferably from 0.001 to 0.05.
Preferably, the low foam formulation comprises 5 to 80 wt.%, more preferably 10 to 50 wt.%, based on 100 wt.% total formulation, of the at least one biocidal quaternary ammonium and/or phosphonium compound.
The low foam formulations of the present invention are stable single phase clear solutions.
Preferably the low foam formulation contains at least one performance additive such as a dye or perfume.
Still another object of the invention is a method for killing or inhibiting the growth of microorganisms, zooplankton, algae and/or fungi comprising applying the above formulations to an aqueous system or to a porous or hard surface.
In a preferred embodiment the porous or hard surface is wood, metal or plastic.
In another preferred embodiment the formulation is used as a wood preservative.
In still another preferred embodiment the formulation is used as a disinfectant or sanitizer for hard surfaces.
In yet another preferred embodiment the aqueous system is selected from the group consisting of cooling waters, waste waters, waters used on oil fields for injection, test or recovery purposes, recreational pool or spa waters, ballast water, and pulp or papermaking slurries.
Most preferably, the aqueous system is cooling water, ballast water or recreational pool or spa water.
Particularly preferred is the application as algaecides in pool or spa waters.
Preferably, the aqueous system contains from 0.1 to 100 ppm, preferably from 0.5 to 50 ppm, of the biocidal quaternary ammonium and/or phosphonium compound.
Exemplary Embodiments of the Invention The invention is further illustrated by the following non-limiting examples.
Examples Method:
Test solutions were prepared from the selected quaternary ammonium compounds and the selected anionic surfactants in 20 C tap water (pH = 7-8, Total Hardness =
160-300 ppm
Preferably, the low foam formulation comprises 5 to 80 wt.%, more preferably 10 to 50 wt.%, based on 100 wt.% total formulation, of the at least one biocidal quaternary ammonium and/or phosphonium compound.
The low foam formulations of the present invention are stable single phase clear solutions.
Preferably the low foam formulation contains at least one performance additive such as a dye or perfume.
Still another object of the invention is a method for killing or inhibiting the growth of microorganisms, zooplankton, algae and/or fungi comprising applying the above formulations to an aqueous system or to a porous or hard surface.
In a preferred embodiment the porous or hard surface is wood, metal or plastic.
In another preferred embodiment the formulation is used as a wood preservative.
In still another preferred embodiment the formulation is used as a disinfectant or sanitizer for hard surfaces.
In yet another preferred embodiment the aqueous system is selected from the group consisting of cooling waters, waste waters, waters used on oil fields for injection, test or recovery purposes, recreational pool or spa waters, ballast water, and pulp or papermaking slurries.
Most preferably, the aqueous system is cooling water, ballast water or recreational pool or spa water.
Particularly preferred is the application as algaecides in pool or spa waters.
Preferably, the aqueous system contains from 0.1 to 100 ppm, preferably from 0.5 to 50 ppm, of the biocidal quaternary ammonium and/or phosphonium compound.
Exemplary Embodiments of the Invention The invention is further illustrated by the following non-limiting examples.
Examples Method:
Test solutions were prepared from the selected quaternary ammonium compounds and the selected anionic surfactants in 20 C tap water (pH = 7-8, Total Hardness =
160-300 ppm
5 as CaCO3 and Total Alkalinity = 150-250 ppm as CaCO3). 150 mL of each test solution was added to a 250 mL stoppered graduated mixing cylinder, the solution was agitated by inverting the cylinder ten times and the foam volume measured immediately after agitation and again after 30 seconds settling time. Also measured was the time for total collapse of the foam ("time to no foam"). All quat concentrations in ppm or percent are on a weight basis and refer to the actual content of active ingredient, unless otherwise indicated.
Example 1 (Reference Example) An alkyl (67% C12, 25% C14, 7% C16, 1% C8,10318) dimethylbenzylammonium chloride (ADBAC; Barquat 50-65B, Lonza Inc., Allendale, NJ) was selected as a representative quaternary ammonium compound for foam evaluation. As shown in Table 1 below, ADBAC produced a substantial amount of foam, generating an initial foam volume of 25 mL and maintaining 10 mL of foam after 30 seconds. As a comparison, the foaming behavior of the polymeric quat poly[oxyethylene(dimethyliminio)ethylene(dimethyliminio)ethylene dichloride]
(WSCP;
Buckman Laboratories International, Inc., Memphis, TN) was also tested.
Example 2 The effect of the anionic surfactant sodium dioctyl sulfosuccinate (NaDOSS) on ADBAC
foaming was determined as described above. The results are shown in Table 1 below. The addition of only a 0.1 molar equivalent of NaDOSS relative to the active quat reduced the initial foam volumes by 85 percent from 25 mL to 4 mL. Even the application of only a 0.02 molar equivalent of NaDOSS resulted in merely 6 mL initial foam volume and complete foam loss within 10 seconds.
Example 3 The ability of NaDOSS to control foam at low concentrations of quaternary ammonium compounds, as they are frequently utilized in water treatment applications such as swimming pool algaecides, was tested at quat concentrations of 2 ppm using the methodology of Example 2. For comparison purposes one test was performed without addition of NaDOSS. The results are shown in Table 1 below. It has been found that NaDOSS concentrations as low as 0.05 ppm can control foaming at 2 ppm quat concentration.
'
Example 1 (Reference Example) An alkyl (67% C12, 25% C14, 7% C16, 1% C8,10318) dimethylbenzylammonium chloride (ADBAC; Barquat 50-65B, Lonza Inc., Allendale, NJ) was selected as a representative quaternary ammonium compound for foam evaluation. As shown in Table 1 below, ADBAC produced a substantial amount of foam, generating an initial foam volume of 25 mL and maintaining 10 mL of foam after 30 seconds. As a comparison, the foaming behavior of the polymeric quat poly[oxyethylene(dimethyliminio)ethylene(dimethyliminio)ethylene dichloride]
(WSCP;
Buckman Laboratories International, Inc., Memphis, TN) was also tested.
Example 2 The effect of the anionic surfactant sodium dioctyl sulfosuccinate (NaDOSS) on ADBAC
foaming was determined as described above. The results are shown in Table 1 below. The addition of only a 0.1 molar equivalent of NaDOSS relative to the active quat reduced the initial foam volumes by 85 percent from 25 mL to 4 mL. Even the application of only a 0.02 molar equivalent of NaDOSS resulted in merely 6 mL initial foam volume and complete foam loss within 10 seconds.
Example 3 The ability of NaDOSS to control foam at low concentrations of quaternary ammonium compounds, as they are frequently utilized in water treatment applications such as swimming pool algaecides, was tested at quat concentrations of 2 ppm using the methodology of Example 2. For comparison purposes one test was performed without addition of NaDOSS. The results are shown in Table 1 below. It has been found that NaDOSS concentrations as low as 0.05 ppm can control foaming at 2 ppm quat concentration.
'
6 Example 4 The alternative anionic surfactants sodium dihexyl sulfosuccinate (NaDHSS) and sodium ditridecyl sulfosuccinate (NaDTSS) were also tested as foam reducing agents using the methodology of Example 2. The results are shown in Table 1 below. It has been found that NaDHSS concentrations as low as 1.1 ppm controlled foaming of 10 ppm quat (corresponding to a molar ratio of anionic surfactant to quat of 0.10) while concentrations as low as 0.2 ppm still showed a small effect. Similar results have been obtained with NaDTSS at concentrations of 1.7 ppm (corresponding to a molar ratio of anionic surfactant to quat of 0.10) and 0.4 ppm, respectively. NaDHSS was preferred as it produced clear solutions at all tested concentrations.
Table 1 Foam Volume Quat Sulfonate Sulfonate/Quat [mLl .Time to No Example No. -Amount Amount Molar Ratio.Foam Is]
Type Type Intial 30 s IPP1111 lIVIIII , 1 50-65B 10 ¨ ¨ 0 25 10 _ >30 -1 WSCP 10 ¨ ¨ 0 0 0 <1 2 50-65B 10 NaDOSS 1.3 0.1 4 0 5 _ 2 50-65B 10 NaDOSS 0.26 0.02 6 0 10 3 50-65B 2 ¨ ¨ 0 20 0 20 3 50-65B 2 ,NaDOSS 0.05 0.02 10 , 0 , 5 4 50-65B 10 NaDHSS 1.1 0.1 10 0 8 4 50-65B 10 NaDHSS 0.2 , 0.02 20 4 >30 _ 4 50-65B 10 NaDTSS 1.7 0.1 10 0 , 4 _ _ 4 50-65B 10 NaDTSS 0.4 0.02 20 2 >30 Example 5 As shown in the preceding examples, NaDOSS can be applied separately to quat-containing solutions to achieve the desired foam reduction. However, for practical reasons, in particular ease of application, it is desirable to provide single formulations (concentrates) containing the quats and the anionic surfactants in an optimized molar ratio.
Therefore the phase stability of two formulations containing Barquat 50-65B
and NaDOSS was tested. The results are shown in Table 2 below.
Table 1 Foam Volume Quat Sulfonate Sulfonate/Quat [mLl .Time to No Example No. -Amount Amount Molar Ratio.Foam Is]
Type Type Intial 30 s IPP1111 lIVIIII , 1 50-65B 10 ¨ ¨ 0 25 10 _ >30 -1 WSCP 10 ¨ ¨ 0 0 0 <1 2 50-65B 10 NaDOSS 1.3 0.1 4 0 5 _ 2 50-65B 10 NaDOSS 0.26 0.02 6 0 10 3 50-65B 2 ¨ ¨ 0 20 0 20 3 50-65B 2 ,NaDOSS 0.05 0.02 10 , 0 , 5 4 50-65B 10 NaDHSS 1.1 0.1 10 0 8 4 50-65B 10 NaDHSS 0.2 , 0.02 20 4 >30 _ 4 50-65B 10 NaDTSS 1.7 0.1 10 0 , 4 _ _ 4 50-65B 10 NaDTSS 0.4 0.02 20 2 >30 Example 5 As shown in the preceding examples, NaDOSS can be applied separately to quat-containing solutions to achieve the desired foam reduction. However, for practical reasons, in particular ease of application, it is desirable to provide single formulations (concentrates) containing the quats and the anionic surfactants in an optimized molar ratio.
Therefore the phase stability of two formulations containing Barquat 50-65B
and NaDOSS was tested. The results are shown in Table 2 below.
7 Table 2 NaDOSS/Quat Molar Quat Content NaDOSS Content Appearance Ratio 110,61 PA]
0.02 49.2 1.2 Single phase, clear 0.10 46.1 50.8 Single phase, clear It has been found that clear phase-stable formulations containing NaDOSS and ADBAC in molar ratios of 0.02 and 0.10 can be prepared. Test solutions with 10 ppm quat were prepared from these formulations and showed essentially the same foaming behavior as those of Example 2.
Example 6 Sodium dioctyl sulfosuccinate (NaDOSS) and sodium dihexyl sulfosuccinate (NaDHSS) were tested in a dynamic recirculation foam test designed to simulate cooling applications.
The dynamic foam test consisted of recirculating a 1.5 liter water sample through a large graduated cylinder at a flow rate of 5.7 liter/min (1.5 GPM). The water conditions were:
total hardness (as CaCO3) 280 ppm, total alkalinity (as CaCO3) 164 ppm, temperature 22 C, and pH = 7.3. Master solutions of the test formulations were added as necessary to achieve the reported concentrations. The results are compiled in Table 3 below.
Table 3 Sample Stabilized Foam Height After 5 Minutes (cm) LF 7.25-8.0 LF + 0.02 mol NaDOSS 4.0 LF + 0.02 mol NaDHSS 6.0 Both tested compounds significantly reduced the foaming properties of 90 ppm active dioctyldimethylammonium chloride (Bardac LF 18, Lonza Inc.). As shown in Table 3, the addition of NaDOSS at a molar ratio (sulfosuccinate/Bardac LF 18) of 0.02 provided a 50% foam reduction, from 8 cm to 4 cm, while addition of NaDHSS at the same molar ratio provided a 25% foam reduction.
=
0.02 49.2 1.2 Single phase, clear 0.10 46.1 50.8 Single phase, clear It has been found that clear phase-stable formulations containing NaDOSS and ADBAC in molar ratios of 0.02 and 0.10 can be prepared. Test solutions with 10 ppm quat were prepared from these formulations and showed essentially the same foaming behavior as those of Example 2.
Example 6 Sodium dioctyl sulfosuccinate (NaDOSS) and sodium dihexyl sulfosuccinate (NaDHSS) were tested in a dynamic recirculation foam test designed to simulate cooling applications.
The dynamic foam test consisted of recirculating a 1.5 liter water sample through a large graduated cylinder at a flow rate of 5.7 liter/min (1.5 GPM). The water conditions were:
total hardness (as CaCO3) 280 ppm, total alkalinity (as CaCO3) 164 ppm, temperature 22 C, and pH = 7.3. Master solutions of the test formulations were added as necessary to achieve the reported concentrations. The results are compiled in Table 3 below.
Table 3 Sample Stabilized Foam Height After 5 Minutes (cm) LF 7.25-8.0 LF + 0.02 mol NaDOSS 4.0 LF + 0.02 mol NaDHSS 6.0 Both tested compounds significantly reduced the foaming properties of 90 ppm active dioctyldimethylammonium chloride (Bardac LF 18, Lonza Inc.). As shown in Table 3, the addition of NaDOSS at a molar ratio (sulfosuccinate/Bardac LF 18) of 0.02 provided a 50% foam reduction, from 8 cm to 4 cm, while addition of NaDHSS at the same molar ratio provided a 25% foam reduction.
=
8 Example 7 The phase stability of two formulations containing Bardac LF 18 and NaDOSS
were tested. As shown in Table 4 below, formulations containing NaDOSS at molar ratios of 0.02 and 0.05 are compatible, providing clear, single phase solutions.
Table 4 NaDOSS/Quat Molar Quat Content NaDOSS Content Appearance Ratio f%1 [0,4,1 0.02 51.0 1.5 Single phase, clear 0.05 50.0 3.6 Single phase, clear
were tested. As shown in Table 4 below, formulations containing NaDOSS at molar ratios of 0.02 and 0.05 are compatible, providing clear, single phase solutions.
Table 4 NaDOSS/Quat Molar Quat Content NaDOSS Content Appearance Ratio f%1 [0,4,1 0.02 51.0 1.5 Single phase, clear 0.05 50.0 3.6 Single phase, clear
Claims (24)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS
1. A method for controlling foam formation in an aqueous system containing at least one biocidal quaternary ammonium and/or phosphonium compound, wherein the at least one quaternary ammonium and/or phosphonium compound is selected from (i) a compound having the formula [QR1R2R3R4]+ X- (I), wherein Q is nitrogen or phosphorus;
R1 and R2 are independently unsubstituted or hydroxy-substituted linear or branched C1-4 alkyl; ¨(CH2CH2O)m CH2CH2OH, or ¨(CH2CH(CH3)O)m CH2CH(CH3)OH, where m in each molecule independently is an integer from 1 to 10;
R3 is an optionally substituted benzyl, ethylbenzyl, naphthylmethyl, or linear or branched C6-22 alkyl;
R4 is an optionally substituted benzyl, ethylbenzyl, methylnaphthyl, or linear or branched C1-22 alkyl or ¨R5(O)n(C6H4)R6, wherein n is 0 or 1;
R5 is C1-8 alkanediyl or ¨(CH2)p-O¨(CH2)q¨ wherein p and q independently are integers from 1 to 8;
R6 is hydrogen or linear or branched C1-12 alkyl;
and X- is a monovalent or one equivalent of a polyvalent anion;
(ii) a compound having the formula R19R20R21R22 Q+X- (II), wherein Q is as defined above, R19, R20, R21, and R22 are independently linear, branched, cyclic or any combination thereof saturated or unsaturated hydrocarbyl groups, X- is a monovalent or one equivalent of a polyvalent anion, and the sum of the carbon atoms numbers of R19, R20, R21 and R22 ranges from to 50;
(iii) a polymeric quaternary ammonium or phosphonium biocide; and (iv) a mixture of two or more quaternary compounds of any of (i) to (iii), said method comprising the addition of at least one anionic diester surfactant in a molar ratio of anionic surfactant to the at least one quaternary ammonium and/or phosphonium compound of from 0.001 to 0.09, to said aqueous system.
R1 and R2 are independently unsubstituted or hydroxy-substituted linear or branched C1-4 alkyl; ¨(CH2CH2O)m CH2CH2OH, or ¨(CH2CH(CH3)O)m CH2CH(CH3)OH, where m in each molecule independently is an integer from 1 to 10;
R3 is an optionally substituted benzyl, ethylbenzyl, naphthylmethyl, or linear or branched C6-22 alkyl;
R4 is an optionally substituted benzyl, ethylbenzyl, methylnaphthyl, or linear or branched C1-22 alkyl or ¨R5(O)n(C6H4)R6, wherein n is 0 or 1;
R5 is C1-8 alkanediyl or ¨(CH2)p-O¨(CH2)q¨ wherein p and q independently are integers from 1 to 8;
R6 is hydrogen or linear or branched C1-12 alkyl;
and X- is a monovalent or one equivalent of a polyvalent anion;
(ii) a compound having the formula R19R20R21R22 Q+X- (II), wherein Q is as defined above, R19, R20, R21, and R22 are independently linear, branched, cyclic or any combination thereof saturated or unsaturated hydrocarbyl groups, X- is a monovalent or one equivalent of a polyvalent anion, and the sum of the carbon atoms numbers of R19, R20, R21 and R22 ranges from to 50;
(iii) a polymeric quaternary ammonium or phosphonium biocide; and (iv) a mixture of two or more quaternary compounds of any of (i) to (iii), said method comprising the addition of at least one anionic diester surfactant in a molar ratio of anionic surfactant to the at least one quaternary ammonium and/or phosphonium compound of from 0.001 to 0.09, to said aqueous system.
2. The method of Claim 1, wherein the molar ratio of the anionic diester surfactant to the at least one quaternary ammonium and/or phosphonium compound is from 0.001 to 0.05.
3. The method of Claim 1 or 2, wherein Q is nitrogen.
4. The method of Claim 1 or 2, wherein the quaternary compound has the formula [QR1R2R3R4]+X-, Q is as defined in Claim 1 or 3, both R1 and R2 are C1-4 alkyl, R3 is a linear or branched C6-22 alkyl, R4 is benzyl or a linear or branched C1-22 alkyl and X- is chloride.
5. The method of any one of Claims 1 to 4, wherein X- is selected from the group consisting of 1/2CO~-, HCO3- and OH-.
6. The method of any one of Claims 1 to 5, wherein the at least one anionic diester surfactant is a sulfonate.
7. The method of Claim 6, wherein the at least one anionic diester surfactant is selected from the group consisting of diamyl sulfosuccinate, dihexyl sulfosuccinate, dioctyl sulfosuccinate, ditridecyl sulfosuccinate, the potassium, sodium and calcium salts of any of the foregoing, and any mixture of any of the foregoing sulfosuccinates and salts.
8. The method of Claim 7, wherein the at least one anionic diester surfactant is selected from the group consisting of dihexyl sulfosuccinate and the potassium, sodium and calcium salts thereof.
9. The method of Claim 7, wherein the at least one anionic diester surfactant is selected from the group consisting of dioctyl sulfosuccinate and the potassium, sodium and calcium salts thereof.
10. The method of any one of Claims 1 to 9, wherein the aqueous system contains from 0.1 to 100 ppm of the biocidal quaternary ammonium and/or phosphonium compound.
11. The method of Claim 10, wherein the aqueous system contains from 0.5 to 50 ppm of the biocidal quaternary ammonium and/or phosphonium compound
12. A single-phase liquid low foam formulation comprising at least one biocidal quaternary ammonium compound and at least one anionic surfactant, wherein the at least one quaternary ammonium compound is selected from (i) a compound having the formula [QR1R2R3R4]+X- (I), wherein Q is nitrogen;
R1and R2 are independently unsubstituted or hydroxy-substituted linear or branched C1-4 alkyl; ¨(CH2CH2O)m CH2CH2OH, or ¨(CH2CH(CH3)O)m CH2CH(CH3)OH, where m in each molecule independently is an integer from 1 to 10;
R3 is benzyl, substituted benzyl, ethylbenzyl, naphthylmethyl, or linear or branched C6-22 alkyl;
R4 is benzyl, substituted benzyl, ethylbenzyl, methylnaphthyl, or linear or branched C1-22 alkyl or ¨R5(O)n(C6H4)R6, wherein n is 0 or 1;
R5 is C1-8 alkanediyl or ¨(CH2)p-O¨(CH2)q¨ wherein p and q independently are integers from 1 to 8;
R6 is hydrogen or linear or branched C1-12 alkyl;
and X- is a monovalent or one equivalent of a polyvalent anion;
(ii) a compound having the formula R19R20R21R22Q+X- (II), wherein Q is as defined above, R19, R20, R21, and R22 are independently linear, branched, cyclic or any combination thereof saturated or unsaturated hydrocarbyl groups, X- is a monovalent or one equivalent of a polyvalent anion, and the sum of the carbon atoms numbers of R19, R20, R21 and R22 ranges from to 50;
(iii) a polymeric quaternary ammonium biocide; and (iv) a mixture of two or more quaternary compounds of any of (i) to (iii);
wherein the at least one anionic surfactant is a diester;
and wherein the molar ratio of the anionic surfactant(s) to the quaternary ammonium compound(s) is from 0.001 to 0.09.
R1and R2 are independently unsubstituted or hydroxy-substituted linear or branched C1-4 alkyl; ¨(CH2CH2O)m CH2CH2OH, or ¨(CH2CH(CH3)O)m CH2CH(CH3)OH, where m in each molecule independently is an integer from 1 to 10;
R3 is benzyl, substituted benzyl, ethylbenzyl, naphthylmethyl, or linear or branched C6-22 alkyl;
R4 is benzyl, substituted benzyl, ethylbenzyl, methylnaphthyl, or linear or branched C1-22 alkyl or ¨R5(O)n(C6H4)R6, wherein n is 0 or 1;
R5 is C1-8 alkanediyl or ¨(CH2)p-O¨(CH2)q¨ wherein p and q independently are integers from 1 to 8;
R6 is hydrogen or linear or branched C1-12 alkyl;
and X- is a monovalent or one equivalent of a polyvalent anion;
(ii) a compound having the formula R19R20R21R22Q+X- (II), wherein Q is as defined above, R19, R20, R21, and R22 are independently linear, branched, cyclic or any combination thereof saturated or unsaturated hydrocarbyl groups, X- is a monovalent or one equivalent of a polyvalent anion, and the sum of the carbon atoms numbers of R19, R20, R21 and R22 ranges from to 50;
(iii) a polymeric quaternary ammonium biocide; and (iv) a mixture of two or more quaternary compounds of any of (i) to (iii);
wherein the at least one anionic surfactant is a diester;
and wherein the molar ratio of the anionic surfactant(s) to the quaternary ammonium compound(s) is from 0.001 to 0.09.
13. The formulation of Claim 12, wherein the molar ratio of the anionic diester surfactant(s) to the quaternary ammonium compound(s) is from 0.001 to 0.05.
14. The formulation of Claims 12 or 13, comprising 5 to 80 wt.%, based on 100 wt.%
total formulation, of the at least one biocidal quaternary ammonium compound.
total formulation, of the at least one biocidal quaternary ammonium compound.
15. The formulation of Claims 14, comprising 10 to 50 wt.%, based on 100 wt.% total formulation, of the at least one biocidal quaternary ammonium compound.
16. The formulation of any one of Claims 12 to 15, containing a dye or perfume.
17. A method for killing or inhibiting the growth of microorganisms, algae and/or fungi, said method comprising applying the formulation of any one of Claims 12 to 16 to an aqueous system or to a porous or hard surface.
18. The method of Claim 17, wherein the porous or hard surface is wood, metal or plastic.
19. The method of Claim 18, wherein the formulation is used as a wood preservative.
20. The method of Claim 17, wherein the formulation is used as a disinfectant or sanitizer for hard surfaces.
21. The method of Claim 17, wherein the aqueous system is selected from the group consisting of cooling waters, waste waters, waters used on oil fields for injection, test or recovery purposes, recreational pool or spa waters, ballast water, and pulp or paper-making slurries.
22. The method of Claim 21, wherein the aqueous system is cooling water, ballast water or recreational pool or spa water.
23. The method of Claim 21 or 22, wherein the aqueous system contains from 0.1 to 100 ppm of the biocidal quaternary ammonium compound.
24. The method of Claim 23, wherein the aqueous system contains from 0.5 to 50 ppm of the biocidal quaternary ammonium compound.
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US60/854,109 | 2006-10-25 | ||
PCT/EP2007/009271 WO2008049616A1 (en) | 2006-10-25 | 2007-10-25 | Controlled foam aqueous quaternary ammonium and phosphonium compositions |
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CA2670201A1 CA2670201A1 (en) | 2008-05-02 |
CA2670201C true CA2670201C (en) | 2016-01-05 |
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AU2009327415A1 (en) * | 2008-12-18 | 2011-07-07 | Keith Branly | Formulations of broad spectrum biocides and their use in improved methods for the treatment of ballast water |
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CA2909198C (en) * | 2012-04-20 | 2020-06-30 | 9163-0384 Quebec Inc. | Anodized metal product with antimicrobial properties and method for producing the same |
WO2014114851A1 (en) * | 2013-01-25 | 2014-07-31 | Kemira Oyj | Biocide composition and method for treating water |
US9506015B2 (en) | 2014-11-21 | 2016-11-29 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
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CN108697082A (en) * | 2015-11-23 | 2018-10-23 | 美可帮产品公司 | Surface disinfection agent with remaining biocidal properties |
CA3005597A1 (en) * | 2015-11-23 | 2017-06-01 | Microban Products Company | Surface disinfectant with residual biocidal property |
US9670433B1 (en) | 2015-12-28 | 2017-06-06 | Ecolab Usa Inc. | Hard surface cleaning compositions |
JP6904979B2 (en) | 2016-03-01 | 2021-07-21 | エコラボ ユーエスエー インコーポレイティド | Sterilized rinse based on the synergistic effect of quaternary anionic surfactant |
US11503824B2 (en) | 2016-05-23 | 2022-11-22 | Microban Products Company | Touch screen cleaning and protectant composition |
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US20190364895A1 (en) * | 2016-09-13 | 2019-12-05 | Exigence Technologies Inc. | Antimicrobial compounds or precursors thereof comrpising one or more cationic centers and a coating-incorporation group |
WO2019046409A1 (en) | 2017-08-30 | 2019-03-07 | Ecolab Usa Inc. | Molecules having one hydrophobic group and two identical hydrophilic ionic groups and compositions thereof |
BR112020005885A2 (en) | 2017-09-26 | 2020-09-29 | Ecolab Usa Inc. | antimicrobial, virucide, solid antimicrobial and solid virucide compositions, and methods for using an antimicrobial composition and inactivating a virus. |
WO2019126703A1 (en) | 2017-12-22 | 2019-06-27 | Ecolab Usa Inc. | Antimicrobial compositions with enhanced efficacy |
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- 2007-10-25 AR ARP070104746A patent/AR063405A1/en active IP Right Grant
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CA2670201A1 (en) | 2008-05-02 |
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NZ598418A (en) | 2013-03-28 |
TWI445499B (en) | 2014-07-21 |
CN101563140B (en) | 2013-06-19 |
MY151415A (en) | 2014-05-30 |
AU2007308351A1 (en) | 2008-05-02 |
AR063405A1 (en) | 2009-01-28 |
CN101563140A (en) | 2009-10-21 |
AU2007308351B2 (en) | 2013-05-16 |
KR101461690B1 (en) | 2014-11-17 |
SG176422A1 (en) | 2011-12-29 |
TW200824564A (en) | 2008-06-16 |
HK1137686A1 (en) | 2010-08-06 |
WO2008049616A1 (en) | 2008-05-02 |
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