US3223704A - Quaternary ammonium sulfamates - Google Patents
Quaternary ammonium sulfamates Download PDFInfo
- Publication number
- US3223704A US3223704A US148029A US14802961A US3223704A US 3223704 A US3223704 A US 3223704A US 148029 A US148029 A US 148029A US 14802961 A US14802961 A US 14802961A US 3223704 A US3223704 A US 3223704A
- Authority
- US
- United States
- Prior art keywords
- ammonium
- sulfamate
- quaternary ammonium
- alkyl
- dimethyl
- 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
Links
- 125000001453 quaternary ammonium group Chemical group 0.000 title description 10
- 150000003863 ammonium salts Chemical group 0.000 claims description 2
- -1 quaternary ammonium radical Chemical class 0.000 description 28
- 239000000243 solution Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 239000003760 tallow Substances 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 4
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004166 Lanolin Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 235000019388 lanolin Nutrition 0.000 description 3
- 229940039717 lanolin Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WHQXERVHVDYJLV-UHFFFAOYSA-N aniline;sulfamic acid Chemical group NS(O)(=O)=O.NC1=CC=CC=C1 WHQXERVHVDYJLV-UHFFFAOYSA-N 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 229940092738 beeswax Drugs 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical class NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical group OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- BJLJBRCPDABXCA-UHFFFAOYSA-N hexyl sulfamate Chemical group CCCCCCOS(N)(=O)=O BJLJBRCPDABXCA-UHFFFAOYSA-N 0.000 description 2
- 230000000622 irritating effect Effects 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- VRGGGAIRTCANAR-UHFFFAOYSA-N piperidine sulfamic acid Chemical group S(N)(O)(=O)=O.N1CCCCC1 VRGGGAIRTCANAR-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- 239000012177 spermaceti Substances 0.000 description 2
- 229940084106 spermaceti Drugs 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 235000019605 sweet taste sensations Nutrition 0.000 description 2
- YGKOYVNJPRSSRX-UHFFFAOYSA-M (4-dodecylphenyl)methyl-trimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC1=CC=C(C[N+](C)(C)C)C=C1 YGKOYVNJPRSSRX-UHFFFAOYSA-M 0.000 description 1
- AMVZBIPRTJSECL-UHFFFAOYSA-N 2-(1-benzyl-2-ethyl-4-octadecyl-4,5-dihydroimidazol-1-ium-1-yl)ethanol Chemical compound C(CCCCCCCCCCCCCCCCC)C1N=C([N+](C1)(CCO)CC1=CC=CC=C1)CC AMVZBIPRTJSECL-UHFFFAOYSA-N 0.000 description 1
- STBQLGGAMIVYMB-UHFFFAOYSA-N 2-(1-benzyl-4,5-dihydroimidazol-1-ium-1-yl)ethanol Chemical compound C=1C=CC=CC=1C[N+]1(CCO)CCN=C1 STBQLGGAMIVYMB-UHFFFAOYSA-N 0.000 description 1
- YGIDVFGMDKEQLG-UHFFFAOYSA-N 2-(1-ethyl-4,5-dihydroimidazol-1-ium-1-yl)ethanol Chemical compound C(C)[N+]1(C=NCC1)CCO YGIDVFGMDKEQLG-UHFFFAOYSA-N 0.000 description 1
- HBCWKICUQHVCFB-UHFFFAOYSA-N 4-methyl-4-tetradecylmorpholin-4-ium Chemical compound CCCCCCCCCCCCCC[N+]1(C)CCOCC1 HBCWKICUQHVCFB-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- VVZBFOKBSDGVGZ-UHFFFAOYSA-N BENZALKONIUM Chemical compound CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 VVZBFOKBSDGVGZ-UHFFFAOYSA-N 0.000 description 1
- UQSXTOAJBPYAPC-UHFFFAOYSA-N CCCCCCCCCCCCC1=NC=CC2=CC=CC=C12.CCCCCCOS(N)(=O)=O Chemical compound CCCCCCCCCCCCC1=NC=CC2=CC=CC=C12.CCCCCCOS(N)(=O)=O UQSXTOAJBPYAPC-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- DMGADLOFNZPLGB-UHFFFAOYSA-N [ethoxy-(2-octylphenyl)-phenoxymethyl]-ethyl-dimethylazanium Chemical compound CCCCCCCCC1=CC=CC=C1C(OCC)([N+](C)(C)CC)OC1=CC=CC=C1 DMGADLOFNZPLGB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- FWLORMQUOWCQPO-UHFFFAOYSA-N benzyl-dimethyl-octadecylazanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 FWLORMQUOWCQPO-UHFFFAOYSA-N 0.000 description 1
- BZLRKHIFCAUPPQ-UHFFFAOYSA-N benzyl-dimethyl-tetradecan-2-ylazanium Chemical compound CCCCCCCCCCCCC(C)[N+](C)(C)CC1=CC=CC=C1 BZLRKHIFCAUPPQ-UHFFFAOYSA-N 0.000 description 1
- QDYLMAYUEZBUFO-UHFFFAOYSA-N cetalkonium chloride Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 QDYLMAYUEZBUFO-UHFFFAOYSA-N 0.000 description 1
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical compound CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 description 1
- 229960004830 cetylpyridinium Drugs 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000008294 cold cream Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- BPSQMWSZGQGXHF-UHFFFAOYSA-N dodecyl-ethyl-dimethylazanium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC BPSQMWSZGQGXHF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WUUOYCPDGWDPRO-UHFFFAOYSA-N ethyl-dimethyl-octadecylazanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CC WUUOYCPDGWDPRO-UHFFFAOYSA-N 0.000 description 1
- DELLBLKQOILBPT-UHFFFAOYSA-N ethyl-dimethyl-tetradecylazanium Chemical compound CCCCCCCCCCCCCC[N+](C)(C)CC DELLBLKQOILBPT-UHFFFAOYSA-N 0.000 description 1
- VCAVAURZPNANDQ-UHFFFAOYSA-N ethyl-hexadecyl-dimethylazanium Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC VCAVAURZPNANDQ-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940042472 mineral oil Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 150000002943 palmitic acids Chemical class 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
- 239000006072 paste Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Definitions
- Quaternary ammonium compounds have heretofore been known to possess germicidal and fungicidal properties; however, these desirable properties were at least partly offset by their irritating effect on the skin and other bodily surfaces when such surfaces are exposed thereto. They were, furthermore, generally unpleasant to the taste so that they could not readily be used for oral hygiene purposes and the like.
- the quaternary ammonium radical of compounds embodying the present invention may be selected from any of the well-known class of quaternary ammonium compounds; for example, the alkyl quaternaries such as lauryl trimethyl ammonium, stearyl trimethyl ammonium, stearyl dimethyl ethyl ammonium, cetyl dimethyl ethyl ammonium, myristyl dimethyl ethyl ammonium, lauryl dimethyl ethyl ammonium, tallow trimethyl ammonium, hydrogenated tallow trimethyl ammonium, coco trimethyl ammonium, di-hydrogenated tallow dimethyl ammonium, di-coco dimethyl ammonium, di-soya dimethyl ammonium, hydrogenated tallow dimethyl ethyl ammonium, coco dimethyl ethyl ammonium, tallow dimethyl ethyl ammonium and soya dimethyl ethyl ammonium; the alkylaryl qua
- the sulfamate radical may be selected from any organic sulfamate and more specifically, may be either an aliphatic, an aromatic, a cyclic or a heterocyclic derivative of sulfamic acid.
- An example of an aliphatic derivative is n-hexyl sulfamate, of a cyclic derivative is cyclo hexyl sulfamate, of a heterocyclic derivative is piperidine sulfamate and of an aromatic derivative is aniline sulfamate.
- the method of preparation comprises mixing stoichiometric amounts of the selected sulfamate and the selected quaternary ammonium salt in an aqueous solution, at ambient temperatures and pressures, whereby both reactants are dissolved in the water at approximately 25% strength and react with each other under vigorous agitation.
- the reaction product separates as a liquid; therefore, to facilitate separation, an excessive amount of the reactants is used, the aqueous layer is separated and the non-aqueous layer is Washed and dried under reduced pressure or in a forced draft oven.
- Example 1 380 grams (0.5 mol) of alkyl dimethyl benzyl ammonium chloride, at 50% strength, is diluted to 25% strength with deionized Water. grams (0.5 mol) of sodium cyclo hexyl sulfamate is dissolved in 300 grams of deionized water. The quaternary solution is then intermixed with the sulfamate solution accompanied by rapid and vigorous agitation. The resulting oil layer is then separated, washed and dried under reduced pressure. The end product, when dried, is a waxy, light yellow product and has a sweet taste.
- Example 2 265 grams (0.5 mol) of a 50% aqueous solution of dodecyl trimethyl ammonium chloride is diluted to 25% strength with deionized water. 100 grams of sodium cyclo hexyl sulfamate is dissolved in 300 grams of water. The two solutions are intermixed and blended. There is no separation since the dodecyl trimethyl ammonium cyclo hexyl sulfamate is completely Water-soluble. The reaction product is isolated by removing the water by evaporation under reduced pressure or in a forced draft oven at F. The residue is then dissolved in 99% isopropanol and filtered to remove any salts. The alcoholic filtrate is then evaporated to remove the alcohol. The end product is a yellow waxy material completely soluble in water and having a sweet taste.
- Example 3 350 grams (1 mol) of anhydrous dodecyl benzyl trimethyl ammonium chloride is dissolved in isopropyl alcohol to make a 25% solution. grams (1 mol) of cyclo hexyl sulfamic acid is dissolved in isopropyl alcohol to make a 25% solution. The two alcoholic solutions are then blended together: 56 grams of KOH pellets are then added and the mixture is thoroughly agitated. The resultant salt is removed by filtration to provide a filtrate comprising an alcoholic solution of dodecyl benzyl trimethyl ammonium cyclo hexyl sulfamate. Upon evaporation of the alcohol, there is provided an end product which is low melting and has a waxy appearance. If desired NaOI-I may be substituted for the KOH.
- Example 4 The same procedure is carried out as in Example 3 except that the KOI-I or NaOH is first dissolved in iso- 3 propyl alcohol and then a stoichiometric amount of this latter solution is used in place of the pellets.
- Illustrative of the biocidal properties of the compounds of the present invention are b acteri ostatic tests whereby each of cyclo hexyl, n-hexyl, aniline and piperidine sulfamiates were used against E. typhosi, E. coli and Staphylococcus aureus. All of these compounds exhibited effective inhibition against Staphylococcus aureus in concentrations as low as 1 part in 10,000 in aqueous solution. They also exhibited effective inhibition against E. coli in concentrations of 1 part in 1,000. A ainst E. typhosi, all we hibited effective inhibition at a concentration of 1 part in 1,000 and the aniline sulfam-ate proved effective in concentrations even as low as 1 part in 10,000.
- the compounds of the present invention may also be complexed with halogens, such as bromine and iodine, to form addition products having enhanced germicidal properties, these products being free from the toxic, irritating and di-scoloring effects of free halogens.
- halogen complexes are easily prepared by dilulting the selected quaternary ammonium halide salt to 10% and the-n heating to about 160 F., after which the selected halogen or halogen complex or halogen solution is added slowly with rapid agitation. The mixture is then cooled to about 75 F. and a stoiehiometric amount of the sodium salt of the sulfamate in 10% aqueous solution is added. Purification then follows the normal procedure as in the examples above.
- the quaternary ammonium sulfamates of the present invention are substantive to both skin and fabrics and are generally water-soluble. They may be used in a variety of liquid and solid compositions where an effective nontoxic, non-irritating, substantive biocidal ingredient is desirable. Furthermore, certain of these compounds, such as the cyclo hexyl sulfamates, are highly desirable because of their sweet, pleasant taste when the composition is utilized for oral hygiene purposes.
- the following examples are illustrative of such compositions:
- Example 5 A biocidally active, sweet-tasting tooth paste is prepared as follows:
- Example 6 A biocid-ally active cold cream is prepared as follows: Component: Parts by wt. Mineral oil 47.9 Beeswax 6.0spermaceti 6.0 Cetyl alcohol 1.0 Lanolin 1.0 Water 38.0 Perfume 0.1
- the mineral oil, beeswax, spermaceti, cetyl alcohol and lanolin are mixed with the 'alkyl dimethyl benzyl ammonium aniline :sulfamate and the mixture is heated to form a melt. It is then cooled to 50 C. and water is added with continuous stirring. It is then cooled, with continuous stirring, to 40 C. At this point, the perfume is added and the mixture is then cooled, with continuous stirring to 25 30 C. to give the final product.
- Example 7 A biocidally active tooth powder is prepared in the following manner:
- the above components are admixed at ambient temperatures to form a granular composition.
- Example 8 An antiseptic lozenge is prepared as follows:
- the above ingredients are intermixed and the mixture 18 brought to a boil with constant stirring. It is then poured into molds and allowed to harden.
- Example 9 A sun-tan cream with biocidal properties is prepared as follows:
- the above components are intermixed at ambient temperature to form a homogenized cream.
- Example 10 A biocidally active hair rinse is prepared in the follow mg manner:
- Example 11 An antiseptic lozenge is prepared as follows:
- Component Parts by weight Sucrose 73.0 Glucose solution in H 0 (50% conc.) 24.0 Glycerin 1.0. Alkyl dimethyl ammonium cyclo hexyl sulfamate The above ingredients are mixed and the mixtureis brought to a boil while constantly being stirred. The mixture is then poured into molds and allowed to harden.
- Example 12 A liquid shampoo with biocidal activity is prepared as follows:
- the fatty acids are intermixed after which first the amine and then the propylene glycol is added. The mixture is then stirred until a clear solution is obtained, after which the alkenyl dirnethy ethyl ammonium n-hexyl sulfamate is added. All the mixing takes place at ambient temperature.
- the above mixture is then diluted with Water to any desired consistency. During this addition of water, the mixture assumes a petrolatum-like consistency but gradually changes to a clear very slightly viscous solution. If the solution becomes cloudy, more of the amine is stirred in, a little at a time, until the solution again becomes clear.
- the final product preferably contains about 3 parts by weight of Water to 1 part by Weight of the above mixture.
- Example 13 A biocidally active industrial cleaning composition is prepared as follows:
- Component Parts by Weight Newtral toilet soap, preferably Na or K soaps of stearic, palmitic or oleic acids (neutraP meaning no excess alkali) 30.0 Bentonite 30.0 Sodium lauryl sulfate 10.0 Lanolin 5.0 Perfume 1.0 Lauryl isoquinolinium n-hexyl sulfamate 1.5
- a biocidally active wash solution is prepared as follows:
- Onyxol 336 lauric acid alkanolamine condensate; a liquid detergent produced by Onyx Oil & Chem. 00., Jersey City, N. J.
- Canboxyl methyl cellulose 0.5 Alkyl dimethyl benzyl ammonium piperidine sulfam-ate-bromine complex containing 10% by Weight bromine 1.0
- a chemical complex consisting of a halogen and a quaternary ammonium organic sulfamate.
- NICHOLAS S. RIZZO Primary Examiner.
Description
United States Patent Ofiiice 3,223,794 Patented Dec. 14*, 1%65 3,223,704 QUATERNARY AMMONIUM SULFAMATES Wiiiiam J. Shihe, in, Riverton, N.J., and Marcus Sitter:- iield, Phiiadelphia, Pa., assiguors to Hollichem Corporation, Camden, N.J., a corporation of New Jersey No Drawing. Filed Oct. 27, 1961, Ser. No. 148,029 7 Claims. (Cl. 260-2471) This invention relates to quaternary ammonium compounds, and it specifically relates to the products resulting from the reaction of quaternary ammonium and certain organic sulfamates.
Quaternary ammonium compounds have heretofore been known to possess germicidal and fungicidal properties; however, these desirable properties were at least partly offset by their irritating effect on the skin and other bodily surfaces when such surfaces are exposed thereto. They were, furthermore, generally unpleasant to the taste so that they could not readily be used for oral hygiene purposes and the like.
It has now been discovered that certain organic sulfamates, when reacted with quaternary ammonium compounds, form products which are at least as biocidally active as the ordinary quaternaries and which are, additionally, devoid of undesirable side reactions on the skin and other bodily surfaces as well as on fabrics and the like. Furthermore, certain of such products are sweettasting and, therefore, particularly suitable for oral hygiene purposes.
The quaternary ammonium radical of compounds embodying the present invention may be selected from any of the well-known class of quaternary ammonium compounds; for example, the alkyl quaternaries such as lauryl trimethyl ammonium, stearyl trimethyl ammonium, stearyl dimethyl ethyl ammonium, cetyl dimethyl ethyl ammonium, myristyl dimethyl ethyl ammonium, lauryl dimethyl ethyl ammonium, tallow trimethyl ammonium, hydrogenated tallow trimethyl ammonium, coco trimethyl ammonium, di-hydrogenated tallow dimethyl ammonium, di-coco dimethyl ammonium, di-soya dimethyl ammonium, hydrogenated tallow dimethyl ethyl ammonium, coco dimethyl ethyl ammonium, tallow dimethyl ethyl ammonium and soya dimethyl ethyl ammonium; the alkylaryl quaternaries such as lauryl dimethyl benzyl ammonium, alkyl dimethyl benzyl ammonium, cetyl dimethyl benzyl ammonium, stearyl dimethyl benzyl ammonium, alkyl dimethyl dichlorobenzyl ammonium, alkyl dimethyl ethyl benzyl ammonium, alkyl dimethyl dimethyl benzyl ammonium, dodecyl benzyl trimethyl ammonium, dodecyl methyl benzyl trimethyl ammonium, octyl phenoxy ethoxy ethyl dimethyl benzyl ammonium, soya dimethyl benzyl ammonium, hydrogenated tallow dimethyl benzyl ammonium, tallow dimethyl benzyl ammonium and coco dimethyl benzyl ammonium; the alkyl and alkylaryl pyridiniums such as coco pyridinium, cetyl pyridinium and dodecyl benzyl pyridinium; the alkyl and alkylaryl isoquinoliniums such as alkyl isoquinolinium, cetyl isoquinoliniurn and dodecyl benzyl isoquinolinium; the alkyl and alkylaryl picoliniums such as alkyl alpha picolinium, alkyl beta picolinium and alkyl gamma picolinum; the imidazoliniums such as alkenyl benzyl hydroxyethyl imidazolinium, alkenyl dichlorobenzyl hydroxyethyl imidazolinium, alkenyl ethyl benzyl hydroxyethyl imidazolinium, alkenyl dichlorobenzyl hydroxyethyl irnidazolinium, coco benzyl hydroxyethyl imidazolinium, coco ethyl hydroxyethyl imidazolinium, stearyl ethyl hydroxyethyl imidazolinium, stearyl benzyl hydroxyethyl imidazolinium, stearyl dichlorobenzyl hydroxyethyl imidazolinium and stearyl ethyl benzyl hydroxyethyl imidazolinium; the morpholiniums such as coco methyl morpholinium and myristyl methyl morpholinium; and the N-pyridiniums such as N-(stearoyl colamino formyl methyl)-pyridinium and N-(lauroyl colamino formyl methyl) -pyridinium.
The sulfamate radical may be selected from any organic sulfamate and more specifically, may be either an aliphatic, an aromatic, a cyclic or a heterocyclic derivative of sulfamic acid. An example of an aliphatic derivative is n-hexyl sulfamate, of a cyclic derivative is cyclo hexyl sulfamate, of a heterocyclic derivative is piperidine sulfamate and of an aromatic derivative is aniline sulfamate.
Each of the above-mentioned types of compound can be prepared in a similar manner with variations depending primarily on differing molecular Weights of the components. In general, the method of preparation comprises mixing stoichiometric amounts of the selected sulfamate and the selected quaternary ammonium salt in an aqueous solution, at ambient temperatures and pressures, whereby both reactants are dissolved in the water at approximately 25% strength and react with each other under vigorous agitation. In most instances, the reaction product separates as a liquid; therefore, to facilitate separation, an excessive amount of the reactants is used, the aqueous layer is separated and the non-aqueous layer is Washed and dried under reduced pressure or in a forced draft oven.
The following examples are illustrative of the preparation of compounds embodying the present invention:
Example 1 380 grams (0.5 mol) of alkyl dimethyl benzyl ammonium chloride, at 50% strength, is diluted to 25% strength with deionized Water. grams (0.5 mol) of sodium cyclo hexyl sulfamate is dissolved in 300 grams of deionized water. The quaternary solution is then intermixed with the sulfamate solution accompanied by rapid and vigorous agitation. The resulting oil layer is then separated, washed and dried under reduced pressure. The end product, when dried, is a waxy, light yellow product and has a sweet taste.
Example 2 265 grams (0.5 mol) of a 50% aqueous solution of dodecyl trimethyl ammonium chloride is diluted to 25% strength with deionized water. 100 grams of sodium cyclo hexyl sulfamate is dissolved in 300 grams of water. The two solutions are intermixed and blended. There is no separation since the dodecyl trimethyl ammonium cyclo hexyl sulfamate is completely Water-soluble. The reaction product is isolated by removing the water by evaporation under reduced pressure or in a forced draft oven at F. The residue is then dissolved in 99% isopropanol and filtered to remove any salts. The alcoholic filtrate is then evaporated to remove the alcohol. The end product is a yellow waxy material completely soluble in water and having a sweet taste.
Example 3 350 grams (1 mol) of anhydrous dodecyl benzyl trimethyl ammonium chloride is dissolved in isopropyl alcohol to make a 25% solution. grams (1 mol) of cyclo hexyl sulfamic acid is dissolved in isopropyl alcohol to make a 25% solution. The two alcoholic solutions are then blended together: 56 grams of KOH pellets are then added and the mixture is thoroughly agitated. The resultant salt is removed by filtration to provide a filtrate comprising an alcoholic solution of dodecyl benzyl trimethyl ammonium cyclo hexyl sulfamate. Upon evaporation of the alcohol, there is provided an end product which is low melting and has a waxy appearance. If desired NaOI-I may be substituted for the KOH.
Example 4 The same procedure is carried out as in Example 3 except that the KOI-I or NaOH is first dissolved in iso- 3 propyl alcohol and then a stoichiometric amount of this latter solution is used in place of the pellets.
The above examples are specific to the preparation of cyclo hexyl sulfamates: however, the previously mentioned aniline, n-hexyl and piperidine sulfam-ates, as well as all other equivalent sulfamates, are prepared in the same manner and in the same proportions, mol for mol, whereby only the particular weights differ depending on the molecular weights of the specific compounds involved.
Illustrative of the biocidal properties of the compounds of the present invention are b acteri ostatic tests whereby each of cyclo hexyl, n-hexyl, aniline and piperidine sulfamiates were used against E. typhosi, E. coli and Staphylococcus aureus. All of these compounds exhibited effective inhibition against Staphylococcus aureus in concentrations as low as 1 part in 10,000 in aqueous solution. They also exhibited effective inhibition against E. coli in concentrations of 1 part in 1,000. A ainst E. typhosi, all we hibited effective inhibition at a concentration of 1 part in 1,000 and the aniline sulfam-ate proved effective in concentrations even as low as 1 part in 10,000.
The compounds of the present invention may also be complexed with halogens, such as bromine and iodine, to form addition products having enhanced germicidal properties, these products being free from the toxic, irritating and di-scoloring effects of free halogens. Such halogen complexes are easily prepared by dilulting the selected quaternary ammonium halide salt to 10% and the-n heating to about 160 F., after which the selected halogen or halogen complex or halogen solution is added slowly with rapid agitation. The mixture is then cooled to about 75 F. and a stoiehiometric amount of the sodium salt of the sulfamate in 10% aqueous solution is added. Purification then follows the normal procedure as in the examples above.
The quaternary ammonium sulfamates of the present invention are substantive to both skin and fabrics and are generally water-soluble. They may be used in a variety of liquid and solid compositions where an effective nontoxic, non-irritating, substantive biocidal ingredient is desirable. Furthermore, certain of these compounds, such as the cyclo hexyl sulfamates, are highly desirable because of their sweet, pleasant taste when the composition is utilized for oral hygiene purposes. The following examples are illustrative of such compositions:
Example 5 A biocidally active, sweet-tasting tooth paste is prepared as follows:
Component: Parts by wt. Glycerin 23.0 Gum tragacanth mucilage (5% in H O) 14.0 Precipitated chalk 49.9 Bentonite 3.0 Sodium lauryl sulfate 3.0 Water 7.0 Dodecyl trimethyl ammonium cyclo hexy sulfamate 1.0
All the above ingredients are thoroughly intermixed at ambient temperatures to form a homogeneous paste.
Example 6 A biocid-ally active cold cream is prepared as follows: Component: Parts by wt. Mineral oil 47.9 Beeswax 6.0 Spermaceti 6.0 Cetyl alcohol 1.0 Lanolin 1.0 Water 38.0 Perfume 0.1
Alkyl dimethyl benzyl ammonium aniline sulfamate 0.1
The mineral oil, beeswax, spermaceti, cetyl alcohol and lanolin are mixed with the 'alkyl dimethyl benzyl ammonium aniline :sulfamate and the mixture is heated to form a melt. It is then cooled to 50 C. and water is added with continuous stirring. It is then cooled, with continuous stirring, to 40 C. At this point, the perfume is added and the mixture is then cooled, with continuous stirring to 25 30 C. to give the final product.
Example 7 A biocidally active tooth powder is prepared in the following manner:
Component: Parts by wt. Precipitated calcium carbonate 94.9 Powdered soap 5.0
Cetyl trimethyl ammonium cyclo hexy sulfamate 0.1
The above components are admixed at ambient temperatures to form a granular composition.
Example 8 An antiseptic lozenge is prepared as follows:
Component: Parts by wt.
Sucrose 73.0 Glucose solution in H 0 (50% conc.) 24.0 Glycerin 1.0
Alkyl dimethyl benzyl ammonium cycle hexyl sulfamate 2.0
The above ingredients are intermixed and the mixture 18 brought to a boil with constant stirring. It is then poured into molds and allowed to harden.
Example 9 A sun-tan cream with biocidal properties is prepared as follows:
The above components are intermixed at ambient temperature to form a homogenized cream.
Example 10 A biocidally active hair rinse is prepared in the follow mg manner:
Component: Parts by weight Glyceryl monostearate 3.0 Water 95.0 Cetyl trimethyl ammonium n-hexyl sulfamate 2.0
These ingredients are thoroughly intermixed at ambient temperature to form the final product.
Example 11 An antiseptic lozenge is prepared as follows:
Component: Parts by weight Sucrose 73.0 Glucose solution in H 0 (50% conc.) 24.0 Glycerin 1.0. Alkyl dimethyl ammonium cyclo hexyl sulfamate The above ingredients are mixed and the mixtureis brought to a boil while constantly being stirred. The mixture is then poured into molds and allowed to harden.
Example 12 A liquid shampoo with biocidal activity is prepared as follows:
The fatty acids are intermixed after which first the amine and then the propylene glycol is added. The mixture is then stirred until a clear solution is obtained, after which the alkenyl dirnethy ethyl ammonium n-hexyl sulfamate is added. All the mixing takes place at ambient temperature.
The above mixture is then diluted with Water to any desired consistency. During this addition of water, the mixture assumes a petrolatum-like consistency but gradually changes to a clear very slightly viscous solution. If the solution becomes cloudy, more of the amine is stirred in, a little at a time, until the solution again becomes clear. The final product preferably contains about 3 parts by weight of Water to 1 part by Weight of the above mixture.
Example 13 A biocidally active industrial cleaning composition is prepared as follows:
Component: Parts by Weight Newtral toilet soap, preferably Na or K soaps of stearic, palmitic or oleic acids (neutraP meaning no excess alkali) 30.0 Bentonite 30.0 Sodium lauryl sulfate 10.0 Lanolin 5.0 Perfume 1.0 Lauryl isoquinolinium n-hexyl sulfamate 1.5
A biocidally active wash solution is prepared as follows:
Component: Parts by weight Potassium tripolyphosphate 19.5 Sodium tripolyphosphate 5.0
Ultrawet L (alkyl aryl sulfonate anionic detergent produced by Atlantic Ref. Co.,
Phila., Pa). 33.0 Onyxol 336 (lauric acid alkanolamine condensate; a liquid detergent produced by Onyx Oil & Chem. 00., Jersey City, N. J.) 5.0 Canboxyl methyl cellulose 0.5 Alkyl dimethyl benzyl ammonium piperidine sulfam-ate-bromine complex containing 10% by Weight bromine 1.0
The above components were mixed together at ambient temperature to form the final product.
Unless otherwise specified, all parts and percentages described herein are by weight.
Obviously many modifications and variations of the present invention are possible in the light of the above teachings. It is, therefore, to be understood that within the scope of the appended claims, the invention may be practiced otherwise than as specifically described.
The invention claimed is:
I. Quaternary ammonium organic mono-sulfamate.
2. Quaternary ammonium n-hexyl sulfamate.
3. Quaternary ammonium aniline sulfamate.
4. Quaternary ammonium cyclo hexyl sulfamate.
5. Quaternary ammonium piperidine sulfamate.
6. A chemical complex consisting of a halogen and a quaternary ammonium organic sulfamate.
7. A bacteriocidal quaternary ammonium cyclohexylsulfam-ate.
References Cited by the Examiner UNITED STATES PATENTS 2,212,171 8/1940 Salzberg 260-567.6 2,383,617 8/1945 Robinson 260-501 2,732,393 1/1956 Hardy 260-501 2,746,986 5/1956 Sahyun et a1. 260501 2,809,146 10/1957 Osborn et al 16733 2,891,065 6/1959 Gundel 260293.4 2,926,119 2/1960 Niederhauser 16730 3,109,857 11/1963 Nomine et al. 260501 OTHER REFERENCES Butler et al.: Journal of the American Chemical Society, volume 61, pages 914915 (1939).
Hardy et al.: Journal of the American Chemical Society, volume 74, page 5214 (1952).
Suter et al.: Journal of the American Chemical Society, volume 65, page 5 12 (1943).
NICHOLAS S. RIZZO, Primary Examiner.
IRVING MARCUS, WALTER A. MODANCE, HENRY R. JILES, Examiners.
Claims (1)
1. QUATERNARY AMMONIUM ORGANIC MONO-SULFAMATE.
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US148029A US3223704A (en) | 1961-10-27 | 1961-10-27 | Quaternary ammonium sulfamates |
US480784A US3344018A (en) | 1961-10-27 | 1965-08-18 | Biocidal quaternary ammonium sulfamates |
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US148029A US3223704A (en) | 1961-10-27 | 1961-10-27 | Quaternary ammonium sulfamates |
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US3341414A (en) * | 1964-08-27 | 1967-09-12 | Merck & Co Inc | N-cyclohexylsulfamate solubilized medication |
US3419562A (en) * | 1964-03-17 | 1968-12-31 | Millmaster Onyx Corp | Quaternary ammonium acinitro compounds |
US3427316A (en) * | 1966-05-02 | 1969-02-11 | Millmaster Onyx Corp | Quaternary ammonium hydroxamates |
US3471423A (en) * | 1966-11-07 | 1969-10-07 | Gen Tire & Rubber Co | Polyurethane materials having biocidal properties and their production |
US3484348A (en) * | 1964-04-27 | 1969-12-16 | Monsanto Co | Quaternary ammonium salt recovery |
US3503890A (en) * | 1966-07-29 | 1970-03-31 | Staley Mfg Co A E | Drain cleaner |
US3622672A (en) * | 1969-01-30 | 1971-11-23 | Soc D Etudes Prod Chimique | Synergistic mixture of 5-methyl 7-bromo 8-hydroxy quinoline and n-dodecyl sulphate of 5-methyl 8-hydroxy quinoline |
US3928618A (en) * | 1972-04-10 | 1975-12-23 | Colgate Palmolive Co | Oral compositions |
US4148884A (en) * | 1974-08-30 | 1979-04-10 | Thorogood Douglas E | Certain lodophor disinfectant compositions |
EP0144960A2 (en) * | 1983-12-09 | 1985-06-19 | Sterling Drug Inc. | Dentrifice compositions |
US4614649A (en) * | 1983-12-09 | 1986-09-30 | Sterling Drug Inc. | Antiplaque saccharin salt dentrifices and method of use thereof |
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US3419562A (en) * | 1964-03-17 | 1968-12-31 | Millmaster Onyx Corp | Quaternary ammonium acinitro compounds |
US3484348A (en) * | 1964-04-27 | 1969-12-16 | Monsanto Co | Quaternary ammonium salt recovery |
US3341414A (en) * | 1964-08-27 | 1967-09-12 | Merck & Co Inc | N-cyclohexylsulfamate solubilized medication |
US3427316A (en) * | 1966-05-02 | 1969-02-11 | Millmaster Onyx Corp | Quaternary ammonium hydroxamates |
US3503890A (en) * | 1966-07-29 | 1970-03-31 | Staley Mfg Co A E | Drain cleaner |
US3471423A (en) * | 1966-11-07 | 1969-10-07 | Gen Tire & Rubber Co | Polyurethane materials having biocidal properties and their production |
US3622672A (en) * | 1969-01-30 | 1971-11-23 | Soc D Etudes Prod Chimique | Synergistic mixture of 5-methyl 7-bromo 8-hydroxy quinoline and n-dodecyl sulphate of 5-methyl 8-hydroxy quinoline |
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US8802596B2 (en) | 2005-10-07 | 2014-08-12 | Board Of Trustees Of The University Of Alabama | Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients |
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