US3493660A - Bactericidal quaternary ammonium compositions - Google Patents
Bactericidal quaternary ammonium compositions Download PDFInfo
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- US3493660A US3493660A US638575A US3493660DA US3493660A US 3493660 A US3493660 A US 3493660A US 638575 A US638575 A US 638575A US 3493660D A US3493660D A US 3493660DA US 3493660 A US3493660 A US 3493660A
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- United States
- Prior art keywords
- quaternary ammonium
- alkoxypropyl
- alkyl
- hard water
- bactericide
- 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.)
- Expired - Lifetime
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- 230000000844 anti-bacterial effect Effects 0.000 title description 71
- 239000000203 mixture Substances 0.000 title description 36
- 125000001453 quaternary ammonium group Chemical group 0.000 title description 20
- 239000003899 bactericide agent Substances 0.000 description 43
- -1 alkyl quaternary ammonium compounds Chemical class 0.000 description 37
- 239000008233 hard water Substances 0.000 description 35
- 125000000217 alkyl group Chemical group 0.000 description 23
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000002994 raw material Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000005233 alkylalcohol group Chemical group 0.000 description 7
- 239000012085 test solution Substances 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical class Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003619 algicide Substances 0.000 description 2
- 125000006231 alkoxy propyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PYLFNXWQOKPJMS-UHFFFAOYSA-M [Cl-].C(CCCCCCC)OCCC[N+](C)(C)CCCOCCCCCCCC Chemical compound [Cl-].C(CCCCCCC)OCCC[N+](C)(C)CCCOCCCCCCCC PYLFNXWQOKPJMS-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- JQRYDCPSJSWQGZ-UHFFFAOYSA-N didecylazanium;chloride Chemical compound Cl.CCCCCCCCCCNCCCCCCCCCC JQRYDCPSJSWQGZ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- 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 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 125000001421 myristyl 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])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000913 palmityl 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])([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
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000004079 stearyl 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])([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])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
Definitions
- the efficacy of a bactericide may be measured against two types of bacteria, those referred to as gram positive organisms, e.g., S, aureaus, and those generally referred to as gram negative organisms, e.g., E. coli and S. typhosa.
- gram positive organisms e.g., S, aureaus
- gram negative organisms e.g., E. coli and S. typhosa.
- the bactericidal activity of quaternary ammonium compounds against both gram positive and gram negative organisms is generally known. Substantially all long chain alkyl quaternary ammonium compounds exhibit some bactericidal activity. Those quaternary ammonium bactericides conventionally employed as bactericides have good bactericidal properties when tested against gram positive bacteria by the standard phenol or AOAC use dilution tests. However, the effectiveness of quaternary ammonium bactericides against gram negative organisms, for example, E. coli and S. typhosa has not been as good as might be desired, particularly in the presence of hard water.
- Quaternary ammonium compounds containing a single long chain alkyl radical having from 8 to 18 carbon atoms and a benzyl radical have generally been considered to have the best bactericidal effectiveness against gram negative organisms.
- Maximum bactericidal effectiveness of known quaternary ammonium bactericides is achieved when the monoalkyl radical is a mixture of dodecyl (C tetradecyl (C hexadecyl (C and octadecyl (C radicals.
- Alkyl radicals of lesser chain length have been found to have lower bactericidal effectiveness.
- the bactericidal effectiveness of dialkyl benzyl quaternary ammonium compounds is likewise substantially less than monoalkyl benzyl quaternary ammonium compounds.
- Quaternary ammonium bactericides find many uses as 3,493,660 Patented Feb. 3, 1970 sanitizers, algicides, etc., where they are employed in aqueous systems at relatively low concentrations, e.g., to 1000 ppm. Accordingly, a bactericide should have good bactericidal effectiveness in the presence of hard water.
- the hard water tolerance of a bactericide may be measured by a standard hard water tolerance test, known as the Chambers test.
- the Chambers test is a modification of the Weber-Black test (Journal of the American l-ublic Health Association, 38, 1405 [1948]).
- test solution consisting of one milliliter of a bacterial inoculum, one milliliter of an aqueous solution of the bactericide to be tested, with the remainder being synthetic hard water.
- the concerntration of bacteria in the inoculum is controlled so that the test solution contains between about 75 million and million bacteria per milliliter.
- the percentage of bacteria killed after certain specified intervals of time is measured to determine the tolerance of the bactericide to hard water.
- Known long chain monoalkyl diamethyl benzyl quaternary ammonium bactericides generally have Chambers hard water tolerances between about 200 and about 750. Some specific types of quaternary compounds have higher Chambers values, but these compounds are generally more complex and are more difficult to manufacture. Known quaternary ammonium compounds which do not contain benzyl radicals generally have lesser Chambers hard water tolerances and are not generally considered to be effective bactericides.
- the present invention is directed to a quaternary ammonium composition which exhibits improved bactericidal effectiveness, particularly against gram negative organisms in the presence of hard water, and which had good solubility in Water. More particularly, the invention is directed to a quaternary ammonium bactericide which includes as its principal bactericidal agent a di-(alkoxypropyl)-quaternary ammonium compound or a mixture of di-(alkoxypropyl)-guaternary ammonium compounds having alkoxypropyl radicals which contain alkyl groups having different chain lengths. The alkoxypropyl radicals containing alkyl groups of different chain length may be in the same molecule or in different molecules.
- the bactericide of the invention may contain only di-(alkoxypropyl)-quaternary compounds which have alkoxypropyl radicals containing alkyl groups of the same chain length.
- the Chambers hard water tolerance is less than that obtained when the quaternary ammonium compounds contain alkoxypropyl radicals having alkyl groups of different chain length.
- the hard water tolerance of the bactericide is comparable to that obtained with known monolkyl dimethyl benzyl quaternary ammonium compounds.
- the quaternary ammonium compounds of the present invention have the formula:
- R is a straight or branched chain, saturated or unsaturated alkyl radical of from 8 to carbon atoms
- R is a saturated alkyl of 1 to 3 carbon atoms
- R is a saturated alkyl radical of l to 3 carbon atoms or a benzyl radical
- X is a salt forming anion.
- R and R are preferably methyl radicals.
- the salt forming anion may be a halogen, alkyl sulfate of from 1 to 4 carbon atoms, citrate, tartrate, sulfamate, nitrate, hydroxide, or any other anionic compound which is soluble in water at intended use levels and does not deleteriously affect the bactericide. In most instances a chloride or methyl sulfate anion is employed.
- the quaternary ammonium compounds which form the bactericide of the invention should contain two alkoxypropyl radicals in order to provide the desired bactericidal effectiveness against gram negative organisms in hard water systems.
- Monoalkoxypropyl quaternary ammonium compounds and mixtures of these compounds do not achieve the high bactericidal effectiveness of di-(alkoxypropyl)-quaternary ammonium compounds.
- the bactericidal effectiveness and solubility of the quaternary ammonium compounds is enhanced by the presence of an ether linkage in the alkyl containing radicals. Similar compounds containing dialkyl radicals, but without an ether linkage, have substantially reduced bactericidal effectiveness against gram negative organisms in the presence of hard water.
- Alkyl groups of different chain lengths are obtained in the same molecule when the quaternary ammonium compound is prepared from alkyl alcohol raw materials which are a mixture of different chain length alcohols.
- the alcohol raw material is a 60 percent-40 percent mixture of n-octyl (C and n-decyl (C alcohols)
- the quaternary ammonium compound formed from the mixed alcohol raw materials will contain some molecules having two octyloxypropyl radicals, some molecules having two decyloxypropyl radicals, and some molecules having one octyloxypropyl radical and one decyloxypropyl radical.
- the di-(alkoxypropyl)-quaternary ammonium compounds which form the bactericide may be prepared in accordance with standard techniques.
- One example of such a process includes reacting an alkyl alcohol which may contain mixed alkyl chains with acrylonitrile followed by subsequent hydrogenation of the resulting ether nitrile and finally quaternizing with an alkyl halide or dialkyl sulfate.
- a preferred preparation consists of charging to a reaction vessel an amount of an alkyl alcohol or mixed alkyl alcohols equivalent to about nine moles of the alcohol and about 0.1 percent potassium hydroxide based on the weight of the alcohol.
- An amount of the alkoxypropyl nitrile product equivalent to between 3.5 and 4.0 moles is then charged to a reaction vessel, equipped to withstand pressures of 1000 p.s.i.g., along with about 10 g. of Raney nickel.
- the reactor is then pressurized to about 25 p.s.i.g. with hydrogen and heated to between 300 F and 350 F.
- the hydrogenation reaction is initiated the temperature is held at about 400 F. and the hydrogen pressure increased to 150 p.s.i.g.
- the hydrogen is continually circulated and washed to remove any undesirable gases, such as ammonia, during the course of the reaction.
- the duration of the hydrogenation reaction is between 1 and 3 hours after which the catalyst is removed leaving a di-(alkoxypropyl)-amine product.
- An amount of di-(alkoxypropyl) amine equivalent to about 0.5 mole is then charged to a reaction vessel equipped to withstand pressure up to 500 p.s.i.g. along with 190 grams of isopropanol, 10 grams of water and about 1.25 moles of sodium bicarbonate.
- the reaction vessel is sparged with nitrogen to remove air, and methyl chloride is added until the pressure inside the vessel reaches 50-70 p.s.i.g.
- the vessel is then heated to a temperature between 70 C. and C.
- the reaction mixture is agitated slightly and the reaction is completed in 3 to 5 hours. Periodic venting of the reaction mixture to remove carbon dioxide is advantageous, followed by addition of methyl chloride until a pressure of between 50 to 70 p.s.i.g. is obtained.
- the reaction is considered complete when the free amine value is between 1.50.5. Solid residue is removed by filtering.
- the soluble reaction mixture remaining consists essentially of di-(alkoxypropyl) dimethyl ammonium
- the surprisingly good bactericidal effectiveness of a bactericide of the invention can be demonstrated by the Chambers hard water tolerance test.
- the test solution consisted of 1 milliliter of an inoculum containing E. Coli USPHS No. 198, Strain ATCC No. 11229, containing sulficient bacteria to provide between about 75 million and million bacteria per milliliter of test solution at the start of the test, one milliliter of the bactericide to be tested in an amount to give 200 parts per million of bactericide in the test solution.
- the remainder of the test solution was a synthetic hard water having a controlled hardness equivalent to a stated number of parts per million, calculated as calcium carbonate.
- the kill of E. coli is at least 99.999 percent within 30 seconds, based upon a concentration of bactericide of 200 parts per million of active ingredients.
- the di-(alkoxypropyl)-quaternary ammonium compounds are prepared from a mixture of alkyl alcohols of different chain lengths in order that the quaternary ammonium product will comprise a mixture of different compounds containing, for example, molecules having two C alkyl groups, molecules having two C alkyl groups, and molecules having one C alkyl group, and one C alkyl group.
- mixed alkyl alcohol raw materials it has been determined that at least about 30 percent, and usually about 45 percent, of the di- (alkoxypropyl)-quaternary ammonium product will be of the type which has alkoxypropyl radicals having alkyl groups of different chain lengths on the same molecule.
- Table III illustrates results obtained when mixtures of n-alkyl alcohols were employed as raw materials to prepare mixtures of di-(alkoxypropyl)-dimethyl ammonium chlorides. In each example a 60/40 weight percent mixture of alcohol was used:
- Example Table IV clearly illustrates that an alcohol raw material mixture of between about 20 percent and about percent by weight n-octyl alcohol, and between about 80 percent and about 20 percent n-decyl alcohol results in a di-(alkoxypropyl)-quaternary ammonium product of improved bactericidal etfectiveness. Best results are obtained when the alcohol raw material is a mixture of about 60 percent n-octyl alcohol and about 40 percent n-decyl.
- Di-(alkoxypropyl)-quaternary ammonium compounds in which one methyl radical is replaced by a benzyl radical also exhibit bactericidal effectiveness, although somewhat lesser than similar compounds which do not contain a benzyl radical.
- a C C di-(alkoxypropyD- methyl benzyl quaternary ammonium compound, prepared from a 60/40 mixture of n-octyl and n-decyl alcohol raw materials has a Chambers hard Water tolerance of about 500.
- Bactericides containing the described quaternary ammonium compounds as their principal active agent are useful as sanitizers, algicides and as additives to feed water for poultry.
- the bactericides may be used by themselves or in admixture with various nonionic detergents and builders.
- a bactericide incorporating the compositions of the invention may be prepared by preparing a mixture of 50 percent by weight of the di-(a1koxypropyl)- quaternary ammonium compound, percent by weight isopropanol, or other lower alkyl alcohol, and 35 percent by weight of water. Of course other formulations are also contemplated.
- the quaternary ammonium composition has unusually high bactericidal effectiveness in the presence of hard Water.
- a quaternary ammonium bactericide of high bactericide of high bactericidal effectiveness which includes as its principal bactericidal agent a mixture comprising a compound of the formula R1OCH2CH2CH2 Rs R1OCHZCH2CH2 R4 and a compound of the' formula R30 CHZCH2OHZ R3+ V R20 CHZOIIZCHQ R4
- R and R are straight or branched chain, saturated or unsaturated alkyl of from 8 to 15 carbon atoms
- R is saturated alkyl of 1 to 3 carbon atoms
- R is saturated alkyl of 1 to 3 carbon atoms or benzyl
- X is a water soluble salt forming anion
- R and R are different, and whereby the bactericidal effectiveness of the mixture as tested in hard water is greater than the effectivenessof either component of the mixture alone.
- a quaternary ammonium bactericide in accordance with claim 1 which in addition includes a compound of the formula RzOCIhCHzCfiz ⁇ R4 where R and R are straight or branched chain, saturated or unsaturated alkyl of from 8 to 15 carbon atoms, R is saturated alkyl of 1 to 3 carbon atoms, R; is saturated alkyl of 1 to 3 carbon atoms or benzyl, X is a water soluble salt forming anion, and R and R are different.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63857567A | 1967-05-15 | 1967-05-15 | |
| US63856867A | 1967-05-15 | 1967-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3493660A true US3493660A (en) | 1970-02-03 |
Family
ID=27093121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US638575A Expired - Lifetime US3493660A (en) | 1967-05-15 | 1967-05-15 | Bactericidal quaternary ammonium compositions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3493660A (enrdf_load_stackoverflow) |
| JP (1) | JPS504728B1 (enrdf_load_stackoverflow) |
| DE (1) | DE1768456A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1213361A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050271781A1 (en) * | 2003-03-05 | 2005-12-08 | Burwell Steve R | Antimicrobial solutions and process related thereto |
| US20070082820A1 (en) * | 2002-12-02 | 2007-04-12 | Fred Busch | Composition and Method for Treating Plant Fungal Disease |
| US20100298386A1 (en) * | 2007-10-03 | 2010-11-25 | Burwell Steven R | Compositions and methods for treating mastitis |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2503026A1 (de) * | 1975-01-25 | 1976-07-29 | Hoechst Ag | Waescheweichspuelmittel mit desinfizierenden eigenschaften |
| DE2628157C2 (de) * | 1976-06-23 | 1986-10-30 | Hoechst Ag, 6230 Frankfurt | Quartäre Ammoniumverbindungen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Haarpflegemittel |
| NL7706714A (nl) * | 1976-06-23 | 1977-12-28 | Hoechst Ag | Quaternaire ammoniumverbindingen, werkwijzen voor haar bereiding en haar toepassing in zachtmakende spoelmiddelen voor de was. |
| GB2116966B (en) * | 1982-02-26 | 1986-01-15 | British Petroleum Co Plc | N-oxyalkylated aqueous compositions of quaternary ammenium salt surfactants |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2692286A (en) * | 1953-06-29 | 1954-10-19 | California Research Corp | Preparation of quaternary ammonium halides |
| US2746928A (en) * | 1952-06-26 | 1956-05-22 | California Research Corp | Germicidal detergent compositions |
-
1967
- 1967-05-15 US US638575A patent/US3493660A/en not_active Expired - Lifetime
-
1968
- 1968-05-14 GB GB22743/68A patent/GB1213361A/en not_active Expired
- 1968-05-15 DE DE19681768456 patent/DE1768456A1/de active Pending
- 1968-05-15 JP JP43032490A patent/JPS504728B1/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746928A (en) * | 1952-06-26 | 1956-05-22 | California Research Corp | Germicidal detergent compositions |
| US2692286A (en) * | 1953-06-29 | 1954-10-19 | California Research Corp | Preparation of quaternary ammonium halides |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070082820A1 (en) * | 2002-12-02 | 2007-04-12 | Fred Busch | Composition and Method for Treating Plant Fungal Disease |
| US20050271781A1 (en) * | 2003-03-05 | 2005-12-08 | Burwell Steve R | Antimicrobial solutions and process related thereto |
| US20060110506A1 (en) * | 2003-03-05 | 2006-05-25 | Burwell Steve R | Antimicrobial solutions and process related thereto |
| US20090192165A1 (en) * | 2003-03-05 | 2009-07-30 | Burwell Steve R | Antimicrobial solutions and process related thereto |
| US8075936B2 (en) | 2003-03-05 | 2011-12-13 | Byocoat Enterprises, Inc. | Antimicrobial solutions and process related thereto |
| US8080269B2 (en) | 2003-03-05 | 2011-12-20 | Byocoat Enterprises, Inc. | Antimicrobial solutions and process related thereto |
| US8586115B2 (en) | 2003-03-05 | 2013-11-19 | Byocoat Enterprises, Inc. | Antimicrobial solutions and process related thereto |
| US20100298386A1 (en) * | 2007-10-03 | 2010-11-25 | Burwell Steven R | Compositions and methods for treating mastitis |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS504728B1 (enrdf_load_stackoverflow) | 1975-02-24 |
| GB1213361A (en) | 1970-11-25 |
| DE1768456A1 (de) | 1971-09-16 |
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