US3753990A - Phenylbismuth bis(2-pyridinethiol 1-oxide) - Google Patents
Phenylbismuth bis(2-pyridinethiol 1-oxide) Download PDFInfo
- Publication number
- US3753990A US3753990A US00218584A US3753990DA US3753990A US 3753990 A US3753990 A US 3753990A US 00218584 A US00218584 A US 00218584A US 3753990D A US3753990D A US 3753990DA US 3753990 A US3753990 A US 3753990A
- Authority
- US
- United States
- Prior art keywords
- oxide
- pyridinethiol
- sodium
- alkyl
- phenylbismuth
- 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
- ARWJSDBKJGYWET-UHFFFAOYSA-N phenylbismuth Chemical compound [Bi]C1=CC=CC=C1 ARWJSDBKJGYWET-UHFFFAOYSA-N 0.000 title abstract description 44
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 39
- 150000001875 compounds Chemical class 0.000 abstract description 22
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 18
- 230000000843 anti-fungal effect Effects 0.000 abstract description 9
- 229940121375 antifungal agent Drugs 0.000 abstract description 8
- -1 ice amide Chemical class 0.000 description 43
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 239000011734 sodium Substances 0.000 description 20
- 229910052708 sodium Inorganic materials 0.000 description 20
- 244000060011 Cocos nucifera Species 0.000 description 19
- 235000013162 Cocos nucifera Nutrition 0.000 description 19
- 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 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 description 14
- 235000002639 sodium chloride Nutrition 0.000 description 14
- 239000003760 tallow Substances 0.000 description 14
- 239000000344 soap Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 239000003599 detergent Substances 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000271 synthetic detergent Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 8
- 210000003491 skin Anatomy 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000008272 agar Substances 0.000 description 7
- 239000003240 coconut oil Substances 0.000 description 7
- 235000019864 coconut oil Nutrition 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- 239000002453 shampoo Substances 0.000 description 6
- 239000006150 trypticase soy agar Substances 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229940096386 coconut alcohol Drugs 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 5
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical class [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- HJNAJKBRYDFICV-UHFFFAOYSA-M 1-tetradecylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC[N+]1=CC=CC=C1 HJNAJKBRYDFICV-UHFFFAOYSA-M 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 241000222122 Candida albicans Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 238000002768 Kirby-Bauer method Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 241000588770 Proteus mirabilis Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- GQDHGSXQYMVUJR-UHFFFAOYSA-M diphenylbismuthanylium;acetate Chemical compound C=1C=CC=CC=1[Bi](OC(=O)C)C1=CC=CC=C1 GQDHGSXQYMVUJR-UHFFFAOYSA-M 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000001603 reducing effect Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- SIDULKZCBGMXJL-UHFFFAOYSA-N 1-dimethylphosphoryldodecane Chemical compound CCCCCCCCCCCCP(C)(C)=O SIDULKZCBGMXJL-UHFFFAOYSA-N 0.000 description 2
- KRUABTDBQQLWLS-UHFFFAOYSA-N 1-methylsulfinyltetradecane Chemical compound CCCCCCCCCCCCCCS(C)=O KRUABTDBQQLWLS-UHFFFAOYSA-N 0.000 description 2
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 241000193468 Clostridium perfringens Species 0.000 description 2
- 241000186145 Corynebacterium ammoniagenes Species 0.000 description 2
- 241000186427 Cutibacterium acnes Species 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 2
- 241000186810 Erysipelothrix rhusiopathiae Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- 206010024229 Leprosy Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000191938 Micrococcus luteus Species 0.000 description 2
- 241000187492 Mycobacterium marinum Species 0.000 description 2
- 241000187481 Mycobacterium phlei Species 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 241000607715 Serratia marcescens Species 0.000 description 2
- 241000607762 Shigella flexneri Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 241001221452 Staphylococcus faecalis Species 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 241000415797 Vaginicola Species 0.000 description 2
- 241001135144 Vibrio metschnikovii Species 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 210000001099 axilla Anatomy 0.000 description 2
- WEMUIHHUSRGLKW-UHFFFAOYSA-M butyl-methyl-octadecyl-propylphosphanium;nitrite Chemical compound [O-]N=O.CCCCCCCCCCCCCCCCCC[P+](C)(CCC)CCCC WEMUIHHUSRGLKW-UHFFFAOYSA-M 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- UFTJSHRFRZWCOI-UHFFFAOYSA-N dimethyl-nonyl-(3-phenylpropyl)azanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCCCCC[N+](C)(C)CCCC1=CC=CC=C1 UFTJSHRFRZWCOI-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229940055036 mycobacterium phlei Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- DTBGAKBXTDOKLN-UHFFFAOYSA-N oxo(pyridin-2-yl)sulfanium Chemical compound O=[S+]c1ccccn1 DTBGAKBXTDOKLN-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- AVZICXRYXLCFCK-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate;2-dodecylisoquinolin-2-ium Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1.C1=CC=CC2=C[N+](CCCCCCCCCCCC)=CC=C21 AVZICXRYXLCFCK-UHFFFAOYSA-M 0.000 description 1
- NYEOFIBTYDEESJ-UHFFFAOYSA-N 1-[2-[2-(2-dimethylphosphorylethoxy)ethoxy]ethoxy]nonane Chemical compound CCCCCCCCCOCCOCCOCCP(C)(C)=O NYEOFIBTYDEESJ-UHFFFAOYSA-N 0.000 description 1
- MNLXVEGUYZHTJQ-UHFFFAOYSA-N 1-[ethyl(methyl)phosphoryl]tetradecane Chemical compound CCCCCCCCCCCCCCP(C)(=O)CC MNLXVEGUYZHTJQ-UHFFFAOYSA-N 0.000 description 1
- CXRUQTPIHDKFTG-UHFFFAOYSA-N 1-diethylphosphoryldodecane Chemical compound CCCCCCCCCCCCP(=O)(CC)CC CXRUQTPIHDKFTG-UHFFFAOYSA-N 0.000 description 1
- BQLLFEURQGITEW-UHFFFAOYSA-N 1-diethylphosphoryltetradecane Chemical compound CCCCCCCCCCCCCCP(=O)(CC)CC BQLLFEURQGITEW-UHFFFAOYSA-N 0.000 description 1
- JAXNXAGNWJBENQ-UHFFFAOYSA-N 1-dimethylphosphoryldodecan-2-ol Chemical compound CCCCCCCCCCC(O)CP(C)(C)=O JAXNXAGNWJBENQ-UHFFFAOYSA-N 0.000 description 1
- ZFZIAYPKDVEXDG-UHFFFAOYSA-N 1-dimethylphosphoryloctadecane Chemical compound CCCCCCCCCCCCCCCCCCP(C)(C)=O ZFZIAYPKDVEXDG-UHFFFAOYSA-N 0.000 description 1
- ZSGCBBCGHYYEGU-UHFFFAOYSA-N 1-dimethylphosphoryltetradecane Chemical compound CCCCCCCCCCCCCCP(C)(C)=O ZSGCBBCGHYYEGU-UHFFFAOYSA-N 0.000 description 1
- MRXVVGMYMYOILB-UHFFFAOYSA-N 1-dipropylphosphoryldodecane Chemical compound CCCCCCCCCCCCP(=O)(CCC)CCC MRXVVGMYMYOILB-UHFFFAOYSA-N 0.000 description 1
- VMWIXXSXYKVMKL-UHFFFAOYSA-N 1-dodecoxy-4-methylsulfinylbutan-2-ol Chemical compound CCCCCCCCCCCCOCC(O)CCS(C)=O VMWIXXSXYKVMKL-UHFFFAOYSA-N 0.000 description 1
- NIOSLKHEYQEXQA-UHFFFAOYSA-M 1-dodecyl-2-methylpyridin-1-ium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCC[N+]1=CC=CC=C1C NIOSLKHEYQEXQA-UHFFFAOYSA-M 0.000 description 1
- GKQHIYSTBXDYNQ-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+]1=CC=CC=C1 GKQHIYSTBXDYNQ-UHFFFAOYSA-M 0.000 description 1
- IQDVXXOBJULTFE-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;hydron;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCCCCCC[N+]1=CC=CC=C1 IQDVXXOBJULTFE-UHFFFAOYSA-M 0.000 description 1
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
- CJPDBKNETSCHCH-UHFFFAOYSA-N 1-methylsulfinyldodecane Chemical compound CCCCCCCCCCCCS(C)=O CJPDBKNETSCHCH-UHFFFAOYSA-N 0.000 description 1
- QYRXERZWYVOCEQ-UHFFFAOYSA-N 1-methylsulfinyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCS(C)=O QYRXERZWYVOCEQ-UHFFFAOYSA-N 0.000 description 1
- QFEFGCRDGSKDEI-UHFFFAOYSA-N 1-methylsulfinyltridecan-2-one Chemical compound CCCCCCCCCCCC(=O)CS(C)=O QFEFGCRDGSKDEI-UHFFFAOYSA-N 0.000 description 1
- YVLLFYIFMKAGCT-KHPPLWFESA-N 1-n-[(z)-octadec-9-enyl]propane-1,2-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCC(C)N YVLLFYIFMKAGCT-KHPPLWFESA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ZTWMPLJZGFKRNI-UHFFFAOYSA-N 2-[2-[2-(2-nonoxyethoxy)ethoxy]ethylsulfinyl]ethanol Chemical compound CCCCCCCCCOCCOCCOCCS(=O)CCO ZTWMPLJZGFKRNI-UHFFFAOYSA-N 0.000 description 1
- CGEGSCDKJJXMSB-UHFFFAOYSA-N 2-[dodecyl(2-hydroxyethyl)phosphoryl]ethanol Chemical compound CCCCCCCCCCCCP(=O)(CCO)CCO CGEGSCDKJJXMSB-UHFFFAOYSA-N 0.000 description 1
- MSJLMQTXVKCUCD-UHFFFAOYSA-M 2-dodecylisoquinolin-2-ium;bromide Chemical compound [Br-].C1=CC=CC2=C[N+](CCCCCCCCCCCC)=CC=C21 MSJLMQTXVKCUCD-UHFFFAOYSA-M 0.000 description 1
- AEDQNOLIADXSBB-UHFFFAOYSA-N 3-(dodecylazaniumyl)propanoate Chemical compound CCCCCCCCCCCCNCCC(O)=O AEDQNOLIADXSBB-UHFFFAOYSA-N 0.000 description 1
- TUBRCQBRKJXJEA-UHFFFAOYSA-N 3-[hexadecyl(dimethyl)azaniumyl]propane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CCCS([O-])(=O)=O TUBRCQBRKJXJEA-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- MADJEWLMWMDFAG-UHFFFAOYSA-N 4-ethyl-4-hexadecylmorpholin-4-ium Chemical compound CCCCCCCCCCCCCCCC[N+]1(CC)CCOCC1 MADJEWLMWMDFAG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
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- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
- IWMMSZLFZZPTJY-UHFFFAOYSA-M sodium;3-(dodecylamino)propane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCNCCCS([O-])(=O)=O IWMMSZLFZZPTJY-UHFFFAOYSA-M 0.000 description 1
- HWCHICTXVOMIIF-UHFFFAOYSA-M sodium;3-(dodecylamino)propanoate Chemical compound [Na+].CCCCCCCCCCCCNCCC([O-])=O HWCHICTXVOMIIF-UHFFFAOYSA-M 0.000 description 1
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- 235000019698 starch Nutrition 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
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000005494 tarnishing Methods 0.000 description 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
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- 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
- C11D3/001—Softening compositions
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- 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
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- 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
Definitions
- the present invention relates to a new compound, phenylbismuth bis(2-pyridinethiol l-oxide), which can be formed by the reaction between sodium 2-pyridinethiol 1- oxide and diphenylbismuth acetate.
- This invention also relates to the use of this compound, which is highly efiective against a broad spectrum of bacteria as well as yeast and fungal species, especially when used on the skin, where the compound is fairly substantive, and to compositions, including detergent compositions, containing said compound.
- Phenylbismuth bis(2pyridinethiol l-oxide) has the formula:
- N l o Compositions containing phenylbismuth bis(2-pyridinethiol l-oxide) have excellent broad-spectrum antibacterial and antifungal action.
- Phenylbismuth bis(2-pyridinethiol l-oxide), hereinafter referred to as PBDP, is a yellow powder having a melting point at about 215-218". It is generally insoluble in most common solvents, but is soluble to the extent of about 1% in dimethylsulfoxide, dimethylformamide or dimethylacet- 3,753,990 Patented Aug. 21, 1973 ice amide. The dry solid PBDP is stable and the PBDP appears stable in the presence of soap solutions (pH 9-10) and hydrochloric acid (pH 1).
- Phenylbismuth bis(2-pyridinethiol l-oxide) has been shown to exhibit antibacterial and antifungal effectiveness against, e.g., Gram-positive organisms such as: Brevibacterium ammoniagenes, Erysipelothrix insidiosa, Lact0- bacillus leichmanni, Bacillus subtilus,, Clostridium perfringens, Staphylococcus aureus, Staphylococcus epidermiais, Sarcina lutea, Streptococcus faecalis, Cor ynebacterium acnes, Axilla diphtheriod #16, Oral Streptococcus #126, Mycobacterium phlei, Mycobactei'ium smegmatis, and Mycobacterium balnei; Gram-negative organisms such as: Alkaligenes faecalis, Salmonella typhosa, Shigella flexneri, Mima polymvr
- PBDP Because of the extremely broad antibacterial and antifungal eifectiveness of PBDP it is desirably used as a component of surgical scrub products, bar soaps, shampoos, oral products (e.g., toothpastes, mouthwashes, etc.), first aid sprays, foot powder, deodorants (especially underarm deodorants), first aid creams, toilet bowl cleaners, hard surface cleaners, detergents, paints, cosmetics, spermicides, burn dressings, animal feeds, wood preservatives, mildewcides, germicides, algacides, fungicides, medicines, packing preservatives, etc. In extremely small amounts, e.g., 10 ppm, the 'PBD'P will inhibit the growth of a broad variety of organisms.
- oral products e.g., toothpastes, mouthwashes, etc.
- first aid sprays foot powder, deodorants (especially underarm deodorants)
- first aid creams toilet bowl cleaners, hard surface cleaners, detergents,
- the compositions can be used to destroy organisms, as required.
- the PBDP can be used to treat a variety of diseases and/or organisms including acne, leprosy psoriasis, warts, intestinal parasites, dandruif, pseudomonas or coli bacteria, fungus (e.g., athletes foot), vaginal infections, etc.
- Compositions containing PBDP can be used to treat tissue either to prevent infections or to cure infections.
- PBDP is not inactivated by urine or hair oil, but its activity is somewhat diminished by human serum or human red blood cell lysate. Its activity is somewhat greater in acid to neutral media against S. aureus and E. coli.
- PBDP is substantive to tooth enamel and cellulose.
- PBDP can be used to prevent the growth of plaque in the mouth and can be used against gingivitis. Also, it can be used on bandages, diapers, and sanitary napkins to prevent infections, diaper rash, odor, etc.
- PBDP can also be used as a slimicide and preservative for paper and wood.
- Phenylbismuth bis(2-pyridinethiol l-oxide) can be prepared by reacting diphenylbismuth acetate with sodium Z-pyridinethiol l-oxide in a 1:1 molar ratio in a solvent such as dimethyl formamide. The compound, a yellow precipitate, can then be filtered and purified as exemplified hereinafter in Example I.
- phenylbismuth bis(2-pyridinethiol l-oxide) include the reaction of sodium, potassium, ammonium, or lithium 2- pyridinethiol 1 oxide or any other salt containing a loosely held cation with a phenylbismuth dihalide (e.g., a chloride, bromide, or iodide).
- a phenylbismuth dihalide e.g., a chloride, bromide, or iodide
- compositions containing phenylbismuth bis(2-pyridinethiol l-oxide) can be used in aqueous and/ or non-aqueous solvents to provide antibacterial action.
- the compositions will contain from about 0.2% to about 3% phenylbismuth bis(2- pyridinethiol l-oxide), most preferably from about 1% to about 2%.
- Desirable compositions are those containing soap and non-soap synthetic detergent compounds.
- the synthetic detergent compounds are cationic, amphoteric, including zwitterionic or nonionic.
- soap as used herein is meant to designate alkali metal soaps such as the sodium and potassium salts of the higher fatty acids of naturally occurring plant or animal esters, e.g., palm oil, coconut oil, babassu oil, soybean oil, castor oil, tallow, whale and fish oils, grease and lard and mixtures thereof.
- Sodium and potassium soaps can be made by direct saponification of the fats and oils or by the neutralization of the fatty acids which are prepared in a separate manufacturing process.
- Suitable soaps are the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids (C -C Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.
- Anionic synthetic detergents which can be used with the antibacterial, antifungal, and antiyeast compound of the present invention can be broadly defined as the watersoluble salts, including the alkali metal, ammonium and substituted ammonium salts, of organic sulfuric reaction products having in their molecular structure an alkyl radical containing from about 8 to about 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals.
- alkali metal e.g., sodium and potassium
- ammonium and substituted ammonium e.g., lower alkyl ammonium
- alkyl sulfates especially those obtained by sulfating the higher alcohols produced by reducing the glycerides of tallow or coconut oil
- random paraflin sulfonates in which the alkyl group contains from about 8 to about 22 carbon atoms, prepared by treating random paraffin hydrocarbons in sulfur dioxide and chlorine in the presence of light followed by treating with a base
- branched or linear alkyl benzene sulfonates in which the alkyl group contains from about 8 to about 18 carbon atoms, preferably from about to about 14 carbon atoms, especially those of the types described in US.
- the length of the hydrophilic or polyoxyalkylene radical which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
- nonionic synthetic detergents are made available on the market under the trade name of Pluronic. These compounds are formed by condensing ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol.
- the hydrophobic portion of the molecule which, of course, exhibits water insolubility has a molecular weight of from about 1,500 to about 1,800.
- the addition of polyoxyethylene radicals to this hydrophobic portion tends to increase the water solubility of the molecule as a whole and the liquid character of the products is retained up to the point where polyoxyethylene content is about 50% of the total weight of the condensation product.
- nonionic synthetic detergents include:
- the polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration, with ethylene oxide, the said ethylene oxide being present in amounts equal to 10 to 60 moles of ethylene oxide per mole of alkyl phenol.
- the alkyl substituent in such compounds may be derived from polymerized propylene, diisobutylene, octane, or nonane, for example.
- R R R N Long chain tertiary amine oxides corresponding to the following general formula, R R R N 0, wherein R contains an alkyl, alkenyl or monohydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties, and from 0 to 1 glyceryl moiety, and R and R contain from 1 to about 3 carbon atoms and from 0 to about 1 hydroxy group, e.g., methyl, ethyl, propyl, hydroxy ethyl, or hydroxy propyl radicals.
- the arrow in the formula is a conven tional representation of a semi-polar bond.
- amine oxides suitable for use in this invention include dimethyldodecylamine oxide, oleyldi(2 hydroxyethyl)- amine oxide, dimethyloctylamine oxide, dimethyldecylamine, oxide, dimethyltetradecylamine oxide, 3,6,9-trioxaheptadecyldiethylamine oxide, di(2 hydroxyethyl)tetradecylamine oxide, Z-dodecoxyethyldimethylamine oxide, 3 dodecoxy-Z-hydroxypropyldi(3-hydroxypropyl)amine oxide, dimethylhexadecylamine oxide.
- RRR"P- O Long chain tertiary phosphine oxides corresponding to the following general formula RRR"P- O, wherein R contains an alkyl, alkenyl or monohydroxyalkyl radical ranging from 8 to 18 carbon atoms in chain length, from 0 to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety and R and R" are each alkyl or monohydroxyalkyl groups containing from 1 to 3 carbon atoms.
- the arrow in the formula is a conventional representation of a semi-polar bond. Examples of suitable phosphine oxides are:
- dodecyldimethylphosphine oxide dodecyldimethylphosphine oxide, tetradecyldimethylphosphine oxide, tetradecylmethylethylphosphine oxide, 3,6,9-trioxaoctadecyldimethylphosphine oxide, cetyldimethylphosphine Oxide, 3-dodecoxy-2-hydroxypropyldi (Z-hydroxyethyl phosphine oxide, stearyldimethylphosphine oxide, cetylethylpropylphosphine oxide, oleyldiethylphosphine oxide, dodecyldiethylphosphine oxide, tetradecyldiethylphosphine oxide, dodecyldipropylphosphine oxide, dodecyldi(hydroxymethyl)phosphine oxide, dodecyldi(2-hydroxyethyl)phosphine
- Examples include:
- the zwitterionic synthetic detergents useful with the antibacterial agent of the present invention can be broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals can be straight chain or branched, and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
- a general formula for these compounds is:
- R contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety;
- Y is selected from the group consisting of nitrogen, phosphorus, and sulfur atoms;
- R is an alkyl or monohydroxyalkyl group containing 1 to about 3 carbon atoms;
- x is 1 when Y is a sulfur atom and 2 when Y is a nitrogen or phosphorus atom,
- R is an alkylene or hydroxyalkylene of from 1 to about 4 carbon atoms and Z is a radical selected from the group consisting of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.
- Examples include:
- amphoteric synthetic detergents useful in the present invention can be broadly described as derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical can be straight chain or branched and wherein one of the aliphatic substitutents contains from about 8 to about 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
- an anionic water solubilizing group e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
- Examples of compounds falling within this definition are sodium 3-dodecylaminopropionate, sodium 3-dodecylaminopropane sulfonate, dodecyl-fi-alanine, N-alkyl-taurines such as the one prepared by reacting dodecylamine with sodium isethionate according to the teaching of US. Pat. No. 2,658,072, N-higher alkyl aspartic acids such as those produced according to the teaching of US. Pat. No. 2,438,091, and the products sold under the trade name Miranol and described in U.S. Pat. No. 2,528,378.
- Cationic synthetic detergents include those quaternary ammonium, quaternary phosphonium, and ternary sulfonium compounds containing a single straight chain or branched aliphatic radical containing from about six to about 20 carbon atoms such as dodecyltrimethylammonium chloride; nonylbenzylethyldimethylammonium nitrate; tetradecylpyridinium bromide; octadecylbutylpropylmethylphosphonium nitrite; decyldimethylsulfonium chloride; etc.
- Detergent formulations containing the antibacterial compositions of the present invention can also contain from about 0% to about 90%, preferably from about 10% to about 90% of water-soluble alkaline detergency builder salts, either of the organic or inorganic types. Examples of such builder salts can be found in US. Pat. No. 3,336,233, issued Aug. 15, 1967, column 9, lines 2966, which is incorporated herein by reference. However, at a very high pH, the compound may undergo alkaline hydrolysis and accordingly, for long-term stability, the detergent formulations should have a pH of less than about 10 and preferably the pH should be approximately neutral.
- the detergent formulations can also contain any of the usual adjuvants, diluents, and additives, for example, perfumes, anti-tarnishing agents, anti-redeposition agents, dyes, fluorescers, suds builders, suds depressors and the like without detracting from the advantageous properties of the antibacterial compositions of the present invention.
- diluents which may be incorporated into a synthetic detergent bar in amounts of up to about of the bar include soaps, especially alkaline earth metal insoluble soaps (alkaline earth salts of higher fatty acids); starches such as cornstarch; and clays such as china clay or fullers earth.
- Other diluents include inorganic salts such as sodium and potassium chlorides and sulfates. Such diluents add bulk to the bar and improve its cosmetic properties without impairing its detergent or cohesive properties.
- this phenylbisrnuth bis(2- pyridinethiol I-oxide) was purified as follows: 30 g. of the crude material was dissolved in 2,000 ml. dimethylacetamide at about 60 C. The solution was stirred for approximately 5 minutes, during which time the phenylbismuth bis(2-pyridinethiol l-oxide) was dissolved, leaving the impurities which were separated by filtering. The filtrate was then diluted with an equal volume of water to precipitate out the phenylbismuth bis(2-pyridinethiol l-oxide). The mixture was cooled in an ice bath to precipitate as much material as possible, and this. material was then separated by filtering.
- MIC Minimal inhibitory concentration in agar 10,000 ppm. stock solutions of phenylbismuth bis(2- pyridinethiol l-oxide) were prepared in dirnethylformamide (DMF). The active was diluted to the desired test concentration and added to 19-20 ml. of molten trypticase soy agar (TSA) to give a series of graded concentrations (p.p.m.). Thorough rotation of plates assured adequate mixing of the sanitizer before agar solidification. Appropriate control plates containing plain TSA were ineluded. All plates remained at room temperature overnight.
- Staphylococcus aureus (S. a.) Staphylococcus epidermidis (S. ep.) Streptococcus faecalis (St. 1'.) Streptococcus sp. (St. 126) Sarcina lutea (Sar. l.) Diphtheroid sp. (Dip.
- Pseudomonas aerugz'nosa Ps. a.) Escherichia coil (E. c.) Serratia marcescens (S. m.) Klebsiella pneumoniae (K. p.) Enterobacter aerogenes (E.
- Fungistatic tests were performed using a modified gradient plate technique reported by Hunt and Sandham (Applied Microbiology 17 #2:329-30, 1969). Results were as follows: Aspergillus niger5.8 p.p.m.; Microsporum gypseum-1 p.p.m.
- the product was then distributed over the hands and the lather was worked for 90 seconds.
- the hands were then rinsed under running tap water for 30 seconds.
- the four exposures were spread over two days, and on the afternoon of the second day, the subjects washed their hands four times using a blank bar soap containing no antibacterial agents.
- a fifth standardized washing was then done in a basin containing one liter of sterile distilled water with careful rinsing in this basin. Aliquots were taken from the thoroughly mixed basin contents, added to 30 ml. of sterile distilled water in a membrane funnel, and passed through sterile membrane filters with vacuum suction.
- the filters were then incubated on pads saturated with 2x concentrated trypticase soy broth plus horse serum and 1% Tween 80 in plastic dishes for 48 hours at 37 C. Colonies appearing on the filters were counted and these numbers multiplied by the appropriate dilution factor to determine the number of bacteria/ liter in the fifth basin contents. The numbers per basin for each panelist were converted to logarithms to minimize unusually high or low counts. These values were averaged to determine the mean log of the fifth basin bacterial count. Calculation of the log percent reduction for each subject was made using the log of 1.3 10 or 6.1184, an average fifth basin bacterial count obtained from more than 500 handwashings by non-antibacterial soap users. These values were averaged to obtain the mean log percent reduction. The results were as follows:
- Composition #4 Percent Dimethyl coconut 1 amine oxide 8.0 Disodium lauryl beta-iminodipropionate 5.0 Sodium coconut 1 sulfate 4.0 Coconut 2 diethanolamide 1.0 Phenylbismuth bis(2-pyridinethiol l-oxide) 1.0 Perfume 0.5 Color 0.01
- Citric acid to adjust pH to 7.5 Water, balance.
- the alkyl radical is derived from middle cut coconut alcohol and has approximately the following chain length compo sivtplllg C10, 66% C12, 23% C14, and 9% Cm.
- Composition #5 A shampoo composition is obtained by uniformly mixing together the following ingredients:
- Shampoo formulations containing phenylbismuth bis(2- pyridinethiol l-oxide) are desirable since they will control dandruff.
- Acrylamide polymer (contains 5-10 mole percent acrylic acid radicals; monomer is less than 0.05%; viscosity of a 0.5% soln. is about -15 centipoises at 25 C.)
- Salts sodium and potassium chloride and sulfate from detergents
- 1-2 Water Balance Coconut indicates alkyl radicals corresponding to those of middle cut coconut fatty alcohol containing approximately 2% C10, 66% C12, 23% C11, and 9% C15.
- Cream shampoo Composition Percent Sodium coconut glyccryl ether sulfonate (about 29% diglyceryl and the balance substantially monoglyceryl) 14.8 Sodium tallow glyceryl ether sulfonate (about 28% diglyceryl and the balance substantially monoglyceryl) 2.0 Sodium chloride 6.7 Sodium sulfate 3.5 Sodium N-lauroyl sarcosinate 3.0 Phenylbismuth bis(2-pyridinethiol l-oxide) 2.0 Middle-cut coconut 1 diethanolamine 0.5 Acetylated lanolin 1.0 Perfume 0.4 Water Balance 1 2% C10, 66% C12, 23% C14, and 9% C10.
- This bar cleans well and exhibits good odor reducing properties evidencing antibacterial eifectiveness. It reduces the number of bacteria on the skin significantly.
- EXAMPLE VII A granular built synthetic detergent composition having the following formulation can be prepared and the antibacterial compositions of the present invention can be incorporated therein.
- This composition in addition to performing well in its cleaning capacity, imparts considerable antibatcerial activity to fabrics cleansed in its solution.
- dodecyltrimethylammonium chloride nonylbenzylethyldimethylammonium nitrate; tetradecylpyridinium bromide; octadecylbutylpropylmethylphosphonium nitrite; decyldimethylsulfom'um chloride; (hexylphenyl)dimethylbenzylammonium fluoride; eicosyldimethylbenzylphosphonium chloride; coconutalkylmethylmorpholininm nitrate; octadecylmethylbenzylsulfonium sulfate; laurylpyridinium chloride;
- laurylpyridinium bisulfate laurylpyridinium-S-chloro-2-mercaptobenzothiazole; laurylpicolinium-p-toluenesulfonate; tetradecylpyridinium bromide;
- laurylisoquinolinium bromide laurylisoquinolinium saccharinate; alkylisoquinolinium bromide;
- N-cetyl- -ethyl-morpholinium ethosulfate benzalkonium chloride
- R N+X* one R group is fatty
- R.,N+X three R groups are fatty
- tri(hydrogenated tallow) methylammoniurn chloride distilled tallow amine acetate; diamine acetates; N-oleyl propylene diamine monoacetate; sodium tallow alkyl sulfate; potassium coconut alkyl glyceryl ether sulfonate; sodium salt of randomly sulfonated paraffin containing an average of 15.2 carbon atoms; ammonium tridecyl sulfate; condensation product of octyl phenol with 15 moles of ethylene oxide per mole of octyl phenol;
- a fabric softening composition having the following formulation can be prepared.
- the antibacterial and antifungal effectiveness of the phenylbismuth bis(2-pyridinethiol l-oxide) is especially desirable since the antibacterial and antifungal compound is extremely substantive to cloth.
- Phenylbismuth bis(2-pyridinethiol l-oxide) 1.0 Water Balance Twenty p.p.m. of PBDP were added to a 0.1% aqueous concentration of Downy, a commercial cationic softener containing a ditallowalkyl dimethylammonium chloride active. This composition, when used at 27 C.
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Abstract
PHENYLBISMUTH BIS(2-PYRIDINETHIOL 1-OXIDE), A NEW ANTIBACTERIAL AND ANTIFUNGAL COMPOUND, AND COMPOSITIONS CONTAINING SAME.
Description
United States Patent 3,753,990 PHENYLBISMUTH BIS(2-PYRIDINETHIOL 'l-OXIDE) John Downing Curry, Oxford, Ohio, assignor to The Procter & Gamble Company, Cincinnati, Ohio No Drawing. Continuation-impart of abandoned application Ser. No. 98,086, Dec. 14, 1970. This application Jan. 17, 1972, Ser. No. 218,584
Int. Cl. (307d 31/50 U.S. Cl. 260270 R 1 Claim ABSTRACT OF THE DISCLOSURE Phenylbismuth bis(2-pyridinethiol l-oxide), a new antibacterial and antifungal compound, and compositions containing same.
CROSS-REFERENCE TO RELATED APPLICATION This a continuation-in-part of my copending U.S. patent application, S.N. 98,086 filed Dec. 14, 1970 for Phenylbismuth Di(Pyridinethione-N-Oxide) and Compositions Containing Same now abandoned.
BACKGROUND OF THE INVENTION Field of the invention The present invention relates to a new compound, phenylbismuth bis(2-pyridinethiol l-oxide), which can be formed by the reaction between sodium 2-pyridinethiol 1- oxide and diphenylbismuth acetate. This invention also relates to the use of this compound, which is highly efiective against a broad spectrum of bacteria as well as yeast and fungal species, especially when used on the skin, where the compound is fairly substantive, and to compositions, including detergent compositions, containing said compound.
Prior art SUMMARY OF THE INVENTION Phenylbismuth bis(2pyridinethiol l-oxide) has the formula:
N l o Compositions containing phenylbismuth bis(2-pyridinethiol l-oxide) have excellent broad-spectrum antibacterial and antifungal action.
Phenylbismuth bis(2-pyridinethiol l-oxide), hereinafter referred to as PBDP, is a yellow powder having a melting point at about 215-218". It is generally insoluble in most common solvents, but is soluble to the extent of about 1% in dimethylsulfoxide, dimethylformamide or dimethylacet- 3,753,990 Patented Aug. 21, 1973 ice amide. The dry solid PBDP is stable and the PBDP appears stable in the presence of soap solutions (pH 9-10) and hydrochloric acid (pH 1).
Phenylbismuth bis(2-pyridinethiol l-oxide) has been shown to exhibit antibacterial and antifungal effectiveness against, e.g., Gram-positive organisms such as: Brevibacterium ammoniagenes, Erysipelothrix insidiosa, Lact0- bacillus leichmanni, Bacillus subtilus,, Clostridium perfringens, Staphylococcus aureus, Staphylococcus epidermiais, Sarcina lutea, Streptococcus faecalis, Cor ynebacterium acnes, Axilla diphtheriod #16, Oral Streptococcus #126, Mycobacterium phlei, Mycobactei'ium smegmatis, and Mycobacterium balnei; Gram-negative organisms such as: Alkaligenes faecalis, Salmonella typhosa, Shigella flexneri, Mima polymvrpha, Herellea vaginicola, Hemophilus gallinarum, Proteus mirabilis, Vibrio metschnikovii, Neisseria flavescens, Escherichia coli, Pseudomonas aeruginosa, Serratia marcescens, Klebsiella pneumoniae, and Enterobacter acrogenes; and fungi (including yeasts and dematophytes (such as: Aspergillus niger, Mycrosporum gypseum Trichophyton rubrum, T richophyton interdigitale, Saccharomyces cerevisiae, Candida albicans, and Pityrosporum' o vale.
Because of the extremely broad antibacterial and antifungal eifectiveness of PBDP it is desirably used as a component of surgical scrub products, bar soaps, shampoos, oral products (e.g., toothpastes, mouthwashes, etc.), first aid sprays, foot powder, deodorants (especially underarm deodorants), first aid creams, toilet bowl cleaners, hard surface cleaners, detergents, paints, cosmetics, spermicides, burn dressings, animal feeds, wood preservatives, mildewcides, germicides, algacides, fungicides, medicines, packing preservatives, etc. In extremely small amounts, e.g., 10 ppm, the 'PBD'P will inhibit the growth of a broad variety of organisms. When the PBDP is incorporated in larger amounts, the compositions can be used to destroy organisms, as required. For example, in medicine, both for humans and veterinary medicine, the PBDP can be used to treat a variety of diseases and/or organisms including acne, leprosy psoriasis, warts, intestinal parasites, dandruif, pseudomonas or coli bacteria, fungus (e.g., athletes foot), vaginal infections, etc. Compositions containing PBDP can be used to treat tissue either to prevent infections or to cure infections.
PBDP is not inactivated by urine or hair oil, but its activity is somewhat diminished by human serum or human red blood cell lysate. Its activity is somewhat greater in acid to neutral media against S. aureus and E. coli. PBDP is substantive to tooth enamel and cellulose. Thus, PBDP can be used to prevent the growth of plaque in the mouth and can be used against gingivitis. Also, it can be used on bandages, diapers, and sanitary napkins to prevent infections, diaper rash, odor, etc. PBDP can also be used as a slimicide and preservative for paper and wood.
Preparation of phenylbismuth bis(2-pyridinethiol l-oxide) Phenylbismuth bis(2-pyridinethiol l-oxide) can be prepared by reacting diphenylbismuth acetate with sodium Z-pyridinethiol l-oxide in a 1:1 molar ratio in a solvent such as dimethyl formamide. The compound, a yellow precipitate, can then be filtered and purified as exemplified hereinafter in Example I. Other reactions to form phenylbismuth bis(2-pyridinethiol l-oxide) include the reaction of sodium, potassium, ammonium, or lithium 2- pyridinethiol 1 oxide or any other salt containing a loosely held cation with a phenylbismuth dihalide (e.g., a chloride, bromide, or iodide).
Compositions containing phenylbismuth bis(2-pyridinethiol l-oxide) Phenylbismuth bis(2-pyridinethiol l-oxide) can be used in aqueous and/ or non-aqueous solvents to provide antibacterial action. Preferably, the compositions will contain from about 0.2% to about 3% phenylbismuth bis(2- pyridinethiol l-oxide), most preferably from about 1% to about 2%. Desirable compositions are those containing soap and non-soap synthetic detergent compounds. Preferably, the synthetic detergent compounds are cationic, amphoteric, including zwitterionic or nonionic.
The term soap as used herein is meant to designate alkali metal soaps such as the sodium and potassium salts of the higher fatty acids of naturally occurring plant or animal esters, e.g., palm oil, coconut oil, babassu oil, soybean oil, castor oil, tallow, whale and fish oils, grease and lard and mixtures thereof. Sodium and potassium soaps can be made by direct saponification of the fats and oils or by the neutralization of the fatty acids which are prepared in a separate manufacturing process. Examples of suitable soaps are the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids (C -C Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.
Anionic synthetic detergents which can be used with the antibacterial, antifungal, and antiyeast compound of the present invention can be broadly defined as the watersoluble salts, including the alkali metal, ammonium and substituted ammonium salts, of organic sulfuric reaction products having in their molecular structure an alkyl radical containing from about 8 to about 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals.
Important examples of the synthetic detergents which can be used with the compound of the present invention are the following: alkali metal (e.g., sodium and potassium), ammonium and substituted ammonium (e.g., lower alkyl ammonium) salts of the following: alkyl sulfates, especially those obtained by sulfating the higher alcohols produced by reducing the glycerides of tallow or coconut oil; random paraflin sulfonates, in which the alkyl group contains from about 8 to about 22 carbon atoms, prepared by treating random paraffin hydrocarbons in sulfur dioxide and chlorine in the presence of light followed by treating with a base; branched or linear alkyl benzene sulfonates, in which the alkyl group contains from about 8 to about 18 carbon atoms, preferably from about to about 14 carbon atoms, especially those of the types described in US. Pat. Nos. 2,220,099, and 2,477,383; sodium alkyl glyceryl ether sulfonates, especially those ethers of the higher alcohols derived from tallow and coconut oil; coconut oil fatty acid monoglyceride sulfates and sulfonates; sulfuric acid esters of the reaction product of one mole of a higher fatty alcohol (e.g., tallow or coconut alcohols) and from about 1 to about 6, preferably about 3 moles of ethylene oxide; alkyl phenol ethylene oxide ether sulfates with about 4 units of ethylene oxide per molecule and in which the alkyl radicals contain about 9 carbon atoms; the reaction product of fatty acids esterified with isethionic acid and neutralized with sodium hydroxide where, for example, the fatty acids are derived from coconut oil; fatty acid amides of the methyl tauriue in which the fatty acids, for example, are derived from coconut oil; sulfonated olefins of US. Pat. No. 3,332,880; and others known in the art, a number being specifically set forth in US. Pat. Nos. 2,486,921, 2,486,922 and 2,396,278.
The nonionic synthetic detergentswhich can be used with the antibacterial compound of the present invention may be broadly defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound which may be aliphatic or alkyl-aromatic in nature. The length of the hydrophilic or polyoxyalkylene radical which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
For example, a well-known class of nonionic synthetic detergents is made available on the market under the trade name of Pluronic. These compounds are formed by condensing ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol. The hydrophobic portion of the molecule which, of course, exhibits water insolubility has a molecular weight of from about 1,500 to about 1,800. The addition of polyoxyethylene radicals to this hydrophobic portion tends to increase the water solubility of the molecule as a whole and the liquid character of the products is retained up to the point where polyoxyethylene content is about 50% of the total weight of the condensation product.
Other suitable nonionic synthetic detergents include:
(1) The polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration, with ethylene oxide, the said ethylene oxide being present in amounts equal to 10 to 60 moles of ethylene oxide per mole of alkyl phenol. The alkyl substituent in such compounds may be derived from polymerized propylene, diisobutylene, octane, or nonane, for example.
(2) Those derived from the condensation of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine-products which may be varied in composition depending upon the balance between the hydrophobic and hydrophilic elements which is desired. For example, compounds containing from about 40% to about polyoxyethylene by weight and having a molecular weight of from about 5,000 to about 11,000 resulting from the reaction of ethylene oxide groups with a hydrophobic base constituted of the reaction product of ethylene diamine and excess propylene oxide, said base having a molecular weight of the order of 2,500 to 3,000, are satisfactory.
(3) The condensation product of aliphatic alcohols having from 8 to 18 carbon atoms, in either straight chain or branched chain configuration, with ethylene oxide, e.g., a coconut alcohol ethylene oxide condensate having from 10 to 30 moles of ethylene oxide per mole of coconut alcohol, the coconut alcohol fraction having from 10 to 14 carbon atoms.
(4) Long chain tertiary amine oxides corresponding to the following general formula, R R R N 0, wherein R contains an alkyl, alkenyl or monohydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties, and from 0 to 1 glyceryl moiety, and R and R contain from 1 to about 3 carbon atoms and from 0 to about 1 hydroxy group, e.g., methyl, ethyl, propyl, hydroxy ethyl, or hydroxy propyl radicals. The arrow in the formula is a conven tional representation of a semi-polar bond. Examples of amine oxides suitable for use in this invention include dimethyldodecylamine oxide, oleyldi(2 hydroxyethyl)- amine oxide, dimethyloctylamine oxide, dimethyldecylamine, oxide, dimethyltetradecylamine oxide, 3,6,9-trioxaheptadecyldiethylamine oxide, di(2 hydroxyethyl)tetradecylamine oxide, Z-dodecoxyethyldimethylamine oxide, 3 dodecoxy-Z-hydroxypropyldi(3-hydroxypropyl)amine oxide, dimethylhexadecylamine oxide.
(5) Long chain tertiary phosphine oxides corresponding to the following general formula RRR"P- O, wherein R contains an alkyl, alkenyl or monohydroxyalkyl radical ranging from 8 to 18 carbon atoms in chain length, from 0 to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety and R and R" are each alkyl or monohydroxyalkyl groups containing from 1 to 3 carbon atoms. The arrow in the formula is a conventional representation of a semi-polar bond. Examples of suitable phosphine oxides are:
dodecyldimethylphosphine oxide, tetradecyldimethylphosphine oxide, tetradecylmethylethylphosphine oxide, 3,6,9-trioxaoctadecyldimethylphosphine oxide, cetyldimethylphosphine Oxide, 3-dodecoxy-2-hydroxypropyldi (Z-hydroxyethyl phosphine oxide, stearyldimethylphosphine oxide, cetylethylpropylphosphine oxide, oleyldiethylphosphine oxide, dodecyldiethylphosphine oxide, tetradecyldiethylphosphine oxide, dodecyldipropylphosphine oxide, dodecyldi(hydroxymethyl)phosphine oxide, dodecyldi(2-hydroxyethyl)phosphine oxide, tetradecylmethyl-Z-hydroxypropylphosphine oxide, oleyldimethylphosphine oxide, 2-hydroxydodecyldimethylphosphine oxide.
(6) Long chain dialkyl sulfoxides containing one short chain alkyl or hydroxy alkyl radical of 1 to about 3 carbon atoms (usually methyl) and one long hydrophobic chain which contains alkyl, alkenyl, hydroxy alkyl, or keto alkyl radicals containing from about 8 to about 20 carbon atoms, from to about ethylene oxide moieties and from 0 to l glyceryl moiety. Examples include:
octadecyl methyl sulfoxide,
2-ketotridecyl methyl sulfoxide, 3,6,9-trioxaoctadecyl 2-hydroxyethyl sulfoxide, dodecyl methyl sulfoxide,
oleyl 3-hydroxypropyl sulfoxide,
tetradecyl methyl sulfoxide, S-methoxytridecyl methyl sulfoxide 3-hydroxytridecyl methyl sulfoxide, 3-hydroxy-4-dodecoxybutyl methyl sulfoxide.
The zwitterionic synthetic detergents useful with the antibacterial agent of the present invention can be broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals can be straight chain or branched, and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate. A general formula for these compounds is:
wherein R contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety; Y is selected from the group consisting of nitrogen, phosphorus, and sulfur atoms; R is an alkyl or monohydroxyalkyl group containing 1 to about 3 carbon atoms; x is 1 when Y is a sulfur atom and 2 when Y is a nitrogen or phosphorus atom, R is an alkylene or hydroxyalkylene of from 1 to about 4 carbon atoms and Z is a radical selected from the group consisting of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.
Examples include:
4- [N,N-di Z-hydroxyethyl -N-octadecylammonio] butane-l-carboxylate; 5- [S-3-hydroxypropyl-S-hexadecylsulfonio] 3-hydroxypentane-l-sulfate; 3-[P,P-diethyl-P-3,6,9-trioxatetradecoxylphosphonio]- 2-hydroxy-propane-l-phosphate; 3- [N,N-dipropyl-N-3 -dodecoxy-2-hydroxypropylammonio]-propane-l-phosphonate; 3-(N,N-dimethyl-N-hexadecylammonio)propane-1- sulfonate;
3- (N,N-dimethyl-Nhexadecylammonio -2-hydroxypropane-l-sulfonate;
4- [N,N-di (Z-hydroxyethyl) -N- (2-hydroxydodecyl) ammonio -butanel-carboxylate;
3- [S-ethyl-S- 3-dodecoxy-2-hydroxypropyl sulfonio] propanel-phosphate;
3- [P,P-dimethyl-P-dodecylphosphonio]-propane-1- phosphonate and 5- [N,N-di 3-hydroxypropyl -N-hexadecylammonio] -2- hydroxy-pentanel-sulf ate.
The amphoteric synthetic detergents useful in the present invention can be broadly described as derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical can be straight chain or branched and wherein one of the aliphatic substitutents contains from about 8 to about 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate. Examples of compounds falling within this definition are sodium 3-dodecylaminopropionate, sodium 3-dodecylaminopropane sulfonate, dodecyl-fi-alanine, N-alkyl-taurines such as the one prepared by reacting dodecylamine with sodium isethionate according to the teaching of US. Pat. No. 2,658,072, N-higher alkyl aspartic acids such as those produced according to the teaching of US. Pat. No. 2,438,091, and the products sold under the trade name Miranol and described in U.S. Pat. No. 2,528,378.
Cationic synthetic detergents include those quaternary ammonium, quaternary phosphonium, and ternary sulfonium compounds containing a single straight chain or branched aliphatic radical containing from about six to about 20 carbon atoms such as dodecyltrimethylammonium chloride; nonylbenzylethyldimethylammonium nitrate; tetradecylpyridinium bromide; octadecylbutylpropylmethylphosphonium nitrite; decyldimethylsulfonium chloride; etc.
Detergent formulations containing the antibacterial compositions of the present invention can also contain from about 0% to about 90%, preferably from about 10% to about 90% of water-soluble alkaline detergency builder salts, either of the organic or inorganic types. Examples of such builder salts can be found in US. Pat. No. 3,336,233, issued Aug. 15, 1967, column 9, lines 2966, which is incorporated herein by reference. However, at a very high pH, the compound may undergo alkaline hydrolysis and accordingly, for long-term stability, the detergent formulations should have a pH of less than about 10 and preferably the pH should be approximately neutral.
The detergent formulations can also contain any of the usual adjuvants, diluents, and additives, for example, perfumes, anti-tarnishing agents, anti-redeposition agents, dyes, fluorescers, suds builders, suds depressors and the like without detracting from the advantageous properties of the antibacterial compositions of the present invention.
Examples of diluents which may be incorporated into a synthetic detergent bar in amounts of up to about of the bar include soaps, especially alkaline earth metal insoluble soaps (alkaline earth salts of higher fatty acids); starches such as cornstarch; and clays such as china clay or fullers earth. Other diluents include inorganic salts such as sodium and potassium chlorides and sulfates. Such diluents add bulk to the bar and improve its cosmetic properties without impairing its detergent or cohesive properties.
The antibacterial and antifungal eflicacy of the phenylbismuth bis(2-pyridinethiol l-oxide) is disclosed in the following examples.
EXAMPLE 1 Preparation of phenylbismuth bis(2- pyridinethiol l-oxide) 164.7 grams of diphenylbismuth acetate (.39 mole) were slurried in 2,600 ml. of dimethylformamide. 59.7
grams of sodium Z-pyridinethiol l-oxide (.39' mole, 97.3%) were dissolved in 1,300 ml. of dimethylformamide and 18 g. of water were added to this solution. The two solutions were then mixed while stirring at about 32 C. The solution turned yellow. The solution was continuously stirred for 15 minutes, and then put on a steam bath for 15 minutes where a temperature of 52 C. was attained. The solution was then put on a heating mantle for approximately 1 hour at about 52- 58 C. The solution was then filtered, and the filtrate separated with dichloromethane and water (a ratio of approximately 1:1:2). The top layer which contained water and dimethylforrnamide was discarded. The bottom layer was filtered and washed with water and ether. The resulting impure phenylbismuth bis(2-pyridinethiol l-oxide) was dried in vacuo.
Approximately 350 g. of this phenylbisrnuth bis(2- pyridinethiol I-oxide) was purified as follows: 30 g. of the crude material was dissolved in 2,000 ml. dimethylacetamide at about 60 C. The solution was stirred for approximately 5 minutes, during which time the phenylbismuth bis(2-pyridinethiol l-oxide) was dissolved, leaving the impurities which were separated by filtering. The filtrate was then diluted with an equal volume of water to precipitate out the phenylbismuth bis(2-pyridinethiol l-oxide). The mixture was cooled in an ice bath to precipitate as much material as possible, and this. material was then separated by filtering. The residue was washed with water and ether and dried in a Vacuum to produce essentially pure phenylbismuth bis(2-pyridinethiol 1- oxide). This procedure was repeated until all 350 g. had been processed. The final weight of the material was approximately 332 g. of material having a melting point of about 218 C. The percent of carbon, hydrogen, nitrogen, bismuth, and sulfur present in the phenylbismuth bis(2-pyridinethiol l-oxide) as calculated and as found by analysis are given hereafter.
The phenylbismuth bis(2-pyridinethio l-oxide) prepared according to the process of Example I was tested for antibacterial efiicacy in the following tests:
(1) Minimal inhibitory concentration (MIC) in agar 10,000 ppm. stock solutions of phenylbismuth bis(2- pyridinethiol l-oxide) were prepared in dirnethylformamide (DMF). The active was diluted to the desired test concentration and added to 19-20 ml. of molten trypticase soy agar (TSA) to give a series of graded concentrations (p.p.m.). Thorough rotation of plates assured adequate mixing of the sanitizer before agar solidification. Appropriate control plates containing plain TSA were ineluded. All plates remained at room temperature overnight.
Trypicase soy broth cultures for each test organism (24 hour) were diluted in peptone water to give approxi mately 100 cells per 0.01 ml. The agar plates, marked in sectors, were inoculated by dropping one drop of each diluted culture from a Kline antigen microdropper onto the appropriate sector of agar. The drops were allowed to dry. The plates were incubated 48 hours at 37 C. and then examined for growth. The weakest concentration which completely inhibited growth of an organism was the MIC. The results for the tests were as follows:
Gram-positive organisms:
Staphylococcus aureus (S. a.) Staphylococcus epidermidis (S. ep.) Streptococcus faecalis (St. 1'.) Streptococcus sp. (St. 126) Sarcina lutea (Sar. l.) Diphtheroid sp. (Dip. 16) Brevibacterium ammoniagenes Erysipelothrix insidiosa 1 Lactobacillus leichmanni Bacillus subtilus Clostridium perfringens Corynebacterium aches Axilla diphtheroid #16 Oral Streptococcus #126 Mycobacterium phlei Mycobacterium smegmatis Mycobacterium balnei Gram-negative organisms:
Pseudomonas aerugz'nosa (Ps. a.) Escherichia coil (E. c.) Serratia marcescens (S. m.) Klebsiella pneumoniae (K. p.) Enterobacter aerogenes (E. a.) Alkaligenes faecalis Salmonella typhosa Shigella flexneri Mirna polymorpha Herellea vaginicola Hemophilus gallz'narum Proteus mirabilis Vibrio metschnikovii Nez'sserz'a flavescens NNm mmJ -b-h-h-hNNw IUlUtl- Nrml- A 7-day old culture of Corynebacterium acnes grown anaerobically on brain heart infusion agar plus 1% glu cose (BI-IIA+l% G) was washed from the slant with 10 ml. of peptone water and drop inoculated on plates containing varying concentrations of phenylbismuth bis(2- pyridinethiol l-oxide) in BHIA+1% G. The MIC for this organism was 5 ppm. A similar test was run using Pityrosporum ovale with TSA plus 0.1% of a :5 ratio of oleiczpalmitic acid as the culture medium. The MIC was 5 ppm.
Fungistatic tests were performed using a modified gradient plate technique reported by Hunt and Sandham (Applied Microbiology 17 #2:329-30, 1969). Results were as follows: Aspergillus niger5.8 p.p.m.; Microsporum gypseum-1 p.p.m.
(II) Human corneum disc diffusion test Cornified epidermis was obtained from the plantar surfaces of human volunteers by cutting sheets of uniform thickness (0.4 mm.) with a dermatome. Discs, 6 mm. in diameter, were cut from the sheets with a #2 cork borer. A 1% solution of phenylbismuth bis(2-pyridineth-iol 1- oxide) was prepared by dissolving the material in DMF to make a 10,000 p.p.m. stock solution and adding the required amount of this solution to a 2.5% solution of pHisoderm (a commercially available skin cleansing detergent). Twenty ml. of the 1% solution of phenylbismuth bis(2-pyridiuethiol l-oxide) in pHisoderm was added to a small screw-cap vial. A control vial was prepared containing 20 ml. of the pHisoderm solution alone. Six skin discs were added to each of the vials which then were mechanically agitated for 10 minutes in a 50 C. water bath. The vial contents were transferred to a small beaker where the liquid was removed by suction, and the discs were rinsed three times with 30 ml. of distilled water,
each rinse followed by suction removal of the rinse water. The discs were then dried for two hours on a paper towel covered with a plexiglass shield to prevent air contamination. The dry discs were placed on the surface of 15 m1. of solidified TSA in a Petri dish (one test disc and one control/dish). A l:l0,000 dilution of each of the six test organisms in TSA at 50 C. was prepared. Each Petri dish was overlaid with 10 ml. of agar seeded with one of the organisms. After agar solidification, the disheswere refrigerated overnight to allow diffusion of any sanitizer away from the disc into the medium. The next day, the dishes were placed in a 37 C. incubator for 24 hours. The diameter of any zone which was clear of bacterial growth was measured in mm. These measurements included the 6 mm. diameter disc. A clear zone is indicative of sanitizer retention on the skin after the washpHisoderm control solution.
(HI) Filter disc diffusion test A test which was similar to the skin disc diffusion test was run using filter discs and several types of fabric discs to give an indication of how much sanitizer would remain attached to paper and cloth after rinsing. The results were as follows:
Diameter Clear zone of disc,
mm. S. a E. c. Pa. a
Filter paper 12. 7 34 25 19 Diaper (gauze) 7.0 29 15.5 8 Terrycloth 9. 33 23 18 Untreated muslin- 7. 0 23. 15. o 9 Disheloth 8. 0 25. 5 17 12 (IV) Handwashing test 1% phenylbismuth bis(2-pyridinethiol l-oxide) in pHisoderm was used by 12 subjects who washed their hands four times. These subjects were chosen at random from a large group of available subjects who use non-sanitizer products exclusively for personal hygiene. The regimented washings in the laboratory followed this procedure: The hands were moistened under 100 F. running tap water. The product was squeezed from a plastic bottle into the palm; the amount approximated the size of a ZS-cent piece. The product was then distributed over the hands and the lather was worked for 90 seconds. The hands were then rinsed under running tap water for 30 seconds. The four exposures were spread over two days, and on the afternoon of the second day, the subjects washed their hands four times using a blank bar soap containing no antibacterial agents. A fifth standardized washing was then done in a basin containing one liter of sterile distilled water with careful rinsing in this basin. Aliquots were taken from the thoroughly mixed basin contents, added to 30 ml. of sterile distilled water in a membrane funnel, and passed through sterile membrane filters with vacuum suction. The filters were then incubated on pads saturated with 2x concentrated trypticase soy broth plus horse serum and 1% Tween 80 in plastic dishes for 48 hours at 37 C. Colonies appearing on the filters were counted and these numbers multiplied by the appropriate dilution factor to determine the number of bacteria/ liter in the fifth basin contents. The numbers per basin for each panelist were converted to logarithms to minimize unusually high or low counts. These values were averaged to determine the mean log of the fifth basin bacterial count. Calculation of the log percent reduction for each subject was made using the log of 1.3 10 or 6.1184, an average fifth basin bacterial count obtained from more than 500 handwashings by non-antibacterial soap users. These values were averaged to obtain the mean log percent reduction. The results were as follows:
Log percent reduction:
Mean log 4.7818
A second handwashing test in which the subjects used a measured amount of product (5 ml.) showed the following result:
Log percent reduction:
Mean log 97.48
These tests show that phenylbismuth bis(2-pyridinethiol l-oxide) in a detergent vehicle is effective against normal skin bacterial in vivo under conditions of actual use.
(V) Skin disc drop overlay test S. a J 1 E. c. 2 Ps. a 10 As can be seen from the above data, phenylbismuth bis (Z-pyridinethiol l-oxide) is an effective antibacterial agent against a wide variety of microorganisms (bacteria, yeasts, and fungi) and is substantive to skin, paper, and cloth.
EXAMPLE III Shampoo composition Composition sulfated coconut fatty alcohol-sodium Salt 23 23 Sodium stearate 8. 7 8. 7 Sodium alkyl glyceryl ether sulfonate 1 28. 3 Sodium acyl sareosinate 2 5. 0 Sodium sulfate 0.8 0.8 2.6 Sodium chloride 6. 6 Trisodium phosphate 2. 1 2. 1 Diethanolamide of coconut fatty acids 2. 0 Acetylated lanolin 1. 0 1. 0 1. 0 Perfume 1. 0 1. 0 O. 4 Phenylbismuth bis (2-pyridinethiol 1- 0. 5 1. 0 1. 5 Balance Balance Balance 7. 7 7. 7 7. 4
1 Alkyl radicals derived from fatty alcohol, 25.3% from coconut and 3% form tallow 2 Acyl radicals derived from coconut fatty acids.
Composition #4: Percent Dimethyl coconut 1 amine oxide 8.0 Disodium lauryl beta-iminodipropionate 5.0 Sodium coconut 1 sulfate 4.0 Coconut 2 diethanolamide 1.0 Phenylbismuth bis(2-pyridinethiol l-oxide) 1.0 Perfume 0.5 Color 0.01
Citric acid to adjust pH to 7.5 Water, balance.
The alkyl radical is derived from middle cut coconut alcohol and has approximately the following chain length compo sivtplllg C10, 66% C12, 23% C14, and 9% Cm.
Composition #5: A shampoo composition is obtained by uniformly mixing together the following ingredients:
3% monoethanolamide of coconut oil fatty acids having the following chain length distribution: 16% C 48%): C12, 17% C14, 9% C16, and 10% C18 1% Phenylbismuth bis(2-pyridinethiol l-oxide) 3% diethanolamide of coconut oil fatty acids having the following chain length distribution: 16% C 48% C12, 117% C14, C16 and C13 7% ethanol 0.75% methyl cellulose, a 2% solution of which has a viscosity of 4000 cps. at 68 F. and a gel point of 140 F.
0.75% perfume balance, water.
Shampoo formulations containing phenylbismuth bis(2- pyridinethiol l-oxide) are desirable since they will control dandruff.
EXAMPLE IV Personal use detergent lotion Composition #6: Percent Potassium coconut glyceryl ether sulfonate (about 23% diglyceryl and the balance substantially all monoglyceryl) Sodium coconut glyceryl ether sulfonate (diglyceryl and monoglyceryl content as above) Sodium tallow glyceryl ether sulfonate (diglyceryl and monoglyceryl content as above); the tallow alkyl radicals correspond to those of substantially saturated tallow alcohols containing approximately 2% C 32% C16, and C13 Coconut dimethylamine oxide Sodium salt of sulfated condensation product of one mole of nonylphenol with 4 moles ethylene oxide Potassium pyrophosphate Phenylbismuth bis(2-pyridinethiol l-oxide) Sodium chloride (in addition to that from detergents) Sodium toluene sulfonate Sodium carboxymethylcellulose (degree of substitution 0.65-0.95; viscosity of 1% soln., 1000-2800 cps. at 25 C.) Acrylamide polymer (contains 5-10 mole percent acrylic acid radicals; monomer is less than 0.05%; viscosity of a 0.5% soln. is about -15 centipoises at 25 C.) Salts (sodium and potassium chloride and sulfate from detergents) 1-2 Water Balance Coconut: indicates alkyl radicals corresponding to those of middle cut coconut fatty alcohol containing approximately 2% C10, 66% C12, 23% C11, and 9% C15.
EXAMPLE V Cream shampoo Composition: Percent Sodium coconut glyccryl ether sulfonate (about 29% diglyceryl and the balance substantially monoglyceryl) 14.8 Sodium tallow glyceryl ether sulfonate (about 28% diglyceryl and the balance substantially monoglyceryl) 2.0 Sodium chloride 6.7 Sodium sulfate 3.5 Sodium N-lauroyl sarcosinate 3.0 Phenylbismuth bis(2-pyridinethiol l-oxide) 2.0 Middle-cut coconut 1 diethanolamine 0.5 Acetylated lanolin 1.0 Perfume 0.4 Water Balance 1 2% C10, 66% C12, 23% C14, and 9% C10.
12 EXAMPLE VI acids 17.0 Inorganic salts (sodium and potassium chlorides and sulfates) 32.0 Phenylbismuth bis(2-pyridinethiol l-oxide) 1.0 Water and minors Middle-cut coconut alcohols having a chain length dis tribution substantially as follows: 2% C10, 66% C12, 23% C14 and 9% C10.
2 Balance to 100.
This bar cleans well and exhibits good odor reducing properties evidencing antibacterial eifectiveness. It reduces the number of bacteria on the skin significantly.
EXAMPLE VII A granular built synthetic detergent composition having the following formulation can be prepared and the antibacterial compositions of the present invention can be incorporated therein.
Percent Sodium dodecylbenzene sulfonate 17.5 Sodium tripolyphosphate 50.0 Sodium sulphate 14.0 Sodium silicate (SiO :Na O=2:1) 7.0 Phenylbismuth bis(2-pyridinethiol l-oxide) 3.0 Water and minors 1 Balance to 100.
This composition, in addition to performing well in its cleaning capacity, imparts considerable antibatcerial activity to fabrics cleansed in its solution.
Substantially equivalent results are obtained, i.e., good cleaning and good odor reducing properties when the sodium dodecylbenzene sulfonate of Example VII is replaced, on an equal weight basis, by the following:
dodecyltrimethylammonium chloride; nonylbenzylethyldimethylammonium nitrate; tetradecylpyridinium bromide; octadecylbutylpropylmethylphosphonium nitrite; decyldimethylsulfom'um chloride; (hexylphenyl)dimethylbenzylammonium fluoride; eicosyldimethylbenzylphosphonium chloride; coconutalkylmethylmorpholininm nitrate; octadecylmethylbenzylsulfonium sulfate; laurylpyridinium chloride;
lanrylpyridinium bromide;
laurylpyridinium bisulfate; laurylpyridinium-S-chloro-2-mercaptobenzothiazole; laurylpicolinium-p-toluenesulfonate; tetradecylpyridinium bromide;
cetylpyridinium chloride;
cetylpyridinium bromide;
laurylisoquinolinium bromide; laurylisoquinolinium saccharinate; alkylisoquinolinium bromide;
N-cetyl- -ethyl-morpholinium ethosulfate; benzalkonium chloride;
monoquaternaries R N+X* one R group is fatty); octadecyltrimethylammoninm chloride;
coconut alkyl trimethylammonium chloride; dodecylbenzyltn'(octyldecyl) ammonium chloride; monoquaternaries R N+X- (two R groups are fatty); dlhexadecyldimethylammonium chloride; di-coconut alkyl dimethylammonium chloride;
13 monoquaternaries R.,N+X (three R groups are fatty); tri(hydrogenated tallow) methylammoniurn chloride; distilled tallow amine acetate; diamine acetates; N-oleyl propylene diamine monoacetate; sodium tallow alkyl sulfate; potassium coconut alkyl glyceryl ether sulfonate; sodium salt of randomly sulfonated paraffin containing an average of 15.2 carbon atoms; ammonium tridecyl sulfate; condensation product of octyl phenol with 15 moles of ethylene oxide per mole of octyl phenol;
dimethyldodecylarnine oxide;
dodecyldimethylphosphine oxide;
tetradecyl methyl sulfoxide;
3- (N,N-dimethyl-N-hexadecylammonio) prop anel-sulfonate;
3-dodecylaminopropionate; and
dodecyl-fl-alanine.
The invention has been described above in conjunction with toilet and laundry detergents. It will be obvious to those skilled in the art, however, that the antibacterial compositions of the present invention can also be beneficially employed in such products as shampoos, foot powders, antiseptic ointments, cosmetic products and the like.
A fabric softening composition having the following formulation can be prepared. The antibacterial and antifungal effectiveness of the phenylbismuth bis(2-pyridinethiol l-oxide) is especially desirable since the antibacterial and antifungal compound is extremely substantive to cloth.
Percent Dialkyl dimethylammonium chloride 75% active ingredient dispersed in isopropanol and water, the dialkyl groups being approximately 24% hexadecyl, 75% octadecyl and 1% octadecenyl 7 The condensation product of 30 moles of ethylene oxide with one mole of coconut alcohol 3 Color and perfume 0.3 Phenylbismuth bis(2-pyridinethiol l-oxide) 1.0 Water Balance Twenty p.p.m. of PBDP were added to a 0.1% aqueous concentration of Downy, a commercial cationic softener containing a ditallowalkyl dimethylammonium chloride active. This composition, when used at 27 C. for ten minutes to treat Dacron-prebrightened, nylon, muslin, nylon-prebrightened, muslin-prebrightened, and Dacronzcotton (65 :35)-prebrightened cloth which had been washed with Ivory Snow, a commercial soap powder, and machine dried, completely controlled the growth of S. aureus, S. faecalis, E. coli, C. albicans, and P. mirabilz's. With similar compositions containing 5 p.p.m. PBDP, one rinse gave complete protection against S. aureus and S. faecalis, after three rinses E. coli and C. albicans are stopped, and after four rinses, P. mirabilis is inhibited. With similar compositions containing 30-40 p.p.m. PBDP, one rinse gave protection against P. aeruginosa on muslin, nylon, and the Dacronzcotton blend.
What is claimed is:
1. Phenylbismuth bis(2-pyridinethiol l-oxide).
References Cited UNITED STATES PATENTS 3,239,411 3/1966 Leebrick 260-270 R 3,247,050 4/1966 Leebrick 260-270 R 3,321,480 5/1967 Schroder 260-270 R 3,583,999 6/1971 Damico 260-270 R 3,236,733 2/1966 Karsten 424-245 3,705,943 12/1972 Kaufman 260-270 R OTHER REFERENCES Tenenbaum, Am. Perfumer & Cosmetics, vol. 86, 33-7 (1971).
Gosse et al., Jour. Soc. Cosmetic Chemists, vol. 20, 603-13 (1969).
Van der Wyk et al., Jour. Soc. Cosmetic Chemists, vol. 15, pp. 761-8 (1964).
DONALD G. DAUS, Primary Examiner US. Cl. X.R.
. UNETED STATES PATENT OFFICE fiERTiFICATE 6F CORREC'HQN Patent No, 3r753r99O D ti d August 21., 1 973 Inventor) John Downing Curry It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
E2ol. 1, line 20 after "This" should read -is. w
Col. 1, line 23, after "Same" should read Col. 1, line 48, "Known" should read -known--. Col. 2 lines 9 & l0 "spider-miais" should read -epidermidis Col. 2, line 20, "dematophytes" should read -dermatophytes. Col. 2, line 40, after "leprosy" should read Col. 4, line 64, after "amine" the should be deleted. Col. 6, line 15, "substitutents" should read -substituents--.
Col. 'Z, line 50, "phenylbismuth bis(2 pyridinethio l-o xide)"' should read phenylbismuth bis(2pyridinethiol l-oxide)-.
Co-l. l0, line 11, "bacterial" should read bacteria-. Col. 10, line L B, "form should read from. Col. 10, line 62, "25% C should read --2% C Col. 12, line 34, "sulph e" should read --sul%%te--.
Signed and sealed this 19th day of March 197b,.
( SEAL Attest:
' EDWARD M. FLETCHER, JR. C. MARSHALL DANN Attesting Officer Commissioner of Patents
Applications Claiming Priority (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21858472A | 1972-01-17 | 1972-01-17 | |
NL7204437A NL7204437A (en) | 1972-01-17 | 1972-04-04 | |
DE2216725A DE2216725A1 (en) | 1972-01-17 | 1972-04-07 | PHENYLWISMUTH-BIS- (2-PYRIDINTHIOL-1OXYDE) AND ITS USE |
FR7212388A FR2178819B1 (en) | 1972-01-17 | 1972-04-07 | |
SE7204611A SE383154B (en) | 1972-04-10 | 1972-04-10 | PHENYLVISMUT BIS (2-PYRIDINTIOL-1-OXIDE) FOR USE AS A DISINFECTANT |
GB1708872 | 1972-04-13 | ||
BE782105A BE782105A (en) | 1972-01-17 | 1972-04-14 | BIS (2-PYRIDINETHIOL-1-OXIDE) OF PHENYLBISMUTH AND COMPOSITIONS CONTAINING THIS PRODUCT. |
JP47052417A JPS4910908A (en) | 1972-01-17 | 1972-05-26 | |
US346396A US3890242A (en) | 1972-01-17 | 1973-03-30 | Antibacterial detergent compositions containing phenylbismuth bis(2-pyridinethiol 1-oxide) |
US00346395A US3824307A (en) | 1972-01-17 | 1973-03-30 | Method of controlling bacteria,yeast and fungal species with phenylbismuth bis(2-pyridinethiol-1-oxide) |
Publications (1)
Publication Number | Publication Date |
---|---|
US3753990A true US3753990A (en) | 1973-08-21 |
Family
ID=27579007
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00218584A Expired - Lifetime US3753990A (en) | 1972-01-17 | 1972-01-17 | Phenylbismuth bis(2-pyridinethiol 1-oxide) |
US346396A Expired - Lifetime US3890242A (en) | 1972-01-17 | 1973-03-30 | Antibacterial detergent compositions containing phenylbismuth bis(2-pyridinethiol 1-oxide) |
US00346395A Expired - Lifetime US3824307A (en) | 1972-01-17 | 1973-03-30 | Method of controlling bacteria,yeast and fungal species with phenylbismuth bis(2-pyridinethiol-1-oxide) |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US346396A Expired - Lifetime US3890242A (en) | 1972-01-17 | 1973-03-30 | Antibacterial detergent compositions containing phenylbismuth bis(2-pyridinethiol 1-oxide) |
US00346395A Expired - Lifetime US3824307A (en) | 1972-01-17 | 1973-03-30 | Method of controlling bacteria,yeast and fungal species with phenylbismuth bis(2-pyridinethiol-1-oxide) |
Country Status (7)
Country | Link |
---|---|
US (3) | US3753990A (en) |
JP (1) | JPS4910908A (en) |
BE (1) | BE782105A (en) |
DE (1) | DE2216725A1 (en) |
FR (1) | FR2178819B1 (en) |
GB (1) | GB1341331A (en) |
NL (1) | NL7204437A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4399130A (en) * | 1982-02-01 | 1983-08-16 | Olin Corporation | Use of metallic salts of pyridine-2-thione-N-oxide to treat or prevent swine exudative epidermitis |
US4401666A (en) * | 1982-02-01 | 1983-08-30 | Olin Corporation | Use of metallic salts of pyridine-2-thione-N-oxide to treat or prevent bovine mastitis |
US5817289A (en) * | 1995-01-26 | 1998-10-06 | Nycomed Imaging As | Non-cluster type bismuth compounds |
US5928671A (en) * | 1995-04-25 | 1999-07-27 | Winthrop University Hospital | Method and composition for inhibiting bacteria |
US6086921A (en) * | 1995-04-25 | 2000-07-11 | Wintrop-University Hospital | Metal/thiol biocides |
US6117412A (en) * | 1995-01-26 | 2000-09-12 | Nycomed Imaging As | Non-cluster type bismuth compounds |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1547361A (en) * | 1975-03-24 | 1979-06-13 | Unilever Ltd | Hair shampoos |
AU513305B2 (en) * | 1975-04-02 | 1980-11-27 | E.B. Michaels Research Associates, Inc. | Antimicrobial compositions |
US4147782A (en) * | 1976-06-24 | 1979-04-03 | William H. Rorer, Inc. | Pharmaceutical detergent composition |
JPS5592283A (en) * | 1978-12-29 | 1980-07-12 | Dai Ichi High Frequency Co Ltd | Pressure-welding method of thin-walled steel pipe and apparatus thereof |
FR2455457A1 (en) * | 1979-05-03 | 1980-11-28 | Oreal | COMPOSITIONS CONTAINING CERTAIN N-OXYPYRIDYL-2-THIOL DERIVATIVES FOR THE STRENGTHENING AND REVITALIZATION OF FRAGILE OR ALTERED NAILS |
JPS6031360B2 (en) * | 1979-12-18 | 1985-07-22 | ライオン株式会社 | liquid detergent composition |
JPS6072831A (en) * | 1983-09-29 | 1985-04-24 | Kao Corp | Composition for vesicle |
EP0195054A1 (en) * | 1984-09-27 | 1986-09-24 | Chevron Research Company | Pesticidal tricycloalkyl-(2-pyridylthio) tin n-oxides |
JPH0621050B2 (en) * | 1985-07-11 | 1994-03-23 | 尚子 浮田 | Antidandruff shampoo |
DE3641579A1 (en) * | 1986-12-05 | 1988-06-16 | Henkel Kgaa | N-ALKYL- AND N-ALKENYLASPARAGINIC ACIDS AS CO-COLLECTORS FOR THE FLOTATION OF NON-SULFIDIC ORES |
US5256334A (en) * | 1988-09-08 | 1993-10-26 | The Research Foundation Of The State University Of New York | Homogeneous radiopaque polymer-organobismuth composites |
AU2001264725A1 (en) * | 2000-05-22 | 2001-12-03 | The Procter And Gamble Company | A kit for caring for a fabric article |
AU2001292237A1 (en) * | 2000-09-28 | 2002-04-08 | Uni-Charm Corporation | Method of diminishing urine odor and article functioning to diminish urine odor |
CN113604290A (en) | 2015-08-21 | 2021-11-05 | 艺康美国股份有限公司 | Pyrithione preservative system in solid rinse aid products |
WO2023022822A1 (en) * | 2021-08-19 | 2023-02-23 | Arxada Ag | Fabric softening and sanitizing composition and method of use |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3281366A (en) * | 1962-02-09 | 1966-10-25 | Procter & Gamble | Synergistic antibacterial compositions |
US3239411A (en) * | 1962-06-14 | 1966-03-08 | M & T Chemicals Inc | Organo bismuth biocide |
DE1545621A1 (en) * | 1963-02-21 | 1969-10-23 | Boehringer Sohn Ingelheim | Process for the preparation of triphenyltin [pyridyl-N-oxide] sulfide |
US3835057A (en) * | 1968-07-15 | 1974-09-10 | Lever Brothers Ltd | Anti-bacterial detergent bar |
US3583999A (en) * | 1968-11-01 | 1971-06-08 | Procter & Gamble | Process for preparing 2-pyridinethiol n-oxides and derivatives thereof |
-
1972
- 1972-01-17 US US00218584A patent/US3753990A/en not_active Expired - Lifetime
- 1972-04-04 NL NL7204437A patent/NL7204437A/xx not_active Application Discontinuation
- 1972-04-07 FR FR7212388A patent/FR2178819B1/fr not_active Expired
- 1972-04-07 DE DE2216725A patent/DE2216725A1/en active Pending
- 1972-04-13 GB GB1708872A patent/GB1341331A/en not_active Expired
- 1972-04-14 BE BE782105A patent/BE782105A/en unknown
- 1972-05-26 JP JP47052417A patent/JPS4910908A/ja active Pending
-
1973
- 1973-03-30 US US346396A patent/US3890242A/en not_active Expired - Lifetime
- 1973-03-30 US US00346395A patent/US3824307A/en not_active Expired - Lifetime
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4399130A (en) * | 1982-02-01 | 1983-08-16 | Olin Corporation | Use of metallic salts of pyridine-2-thione-N-oxide to treat or prevent swine exudative epidermitis |
US4401666A (en) * | 1982-02-01 | 1983-08-30 | Olin Corporation | Use of metallic salts of pyridine-2-thione-N-oxide to treat or prevent bovine mastitis |
US5817289A (en) * | 1995-01-26 | 1998-10-06 | Nycomed Imaging As | Non-cluster type bismuth compounds |
US6117412A (en) * | 1995-01-26 | 2000-09-12 | Nycomed Imaging As | Non-cluster type bismuth compounds |
US6303101B1 (en) | 1995-01-26 | 2001-10-16 | Nycomed Imaging As | Bismuth compounds |
US5928671A (en) * | 1995-04-25 | 1999-07-27 | Winthrop University Hospital | Method and composition for inhibiting bacteria |
US6086921A (en) * | 1995-04-25 | 2000-07-11 | Wintrop-University Hospital | Metal/thiol biocides |
US6248371B1 (en) | 1995-04-25 | 2001-06-19 | Winthrop University Hospital | Metal/thiol biocides |
USRE37793E1 (en) | 1995-04-25 | 2002-07-16 | Winthrop University Hospital | Method and composition for inhibiting bacteria |
Also Published As
Publication number | Publication date |
---|---|
GB1341331A (en) | 1973-12-19 |
US3890242A (en) | 1975-06-17 |
JPS4910908A (en) | 1974-01-30 |
DE2216725A1 (en) | 1973-10-11 |
FR2178819B1 (en) | 1975-10-10 |
BE782105A (en) | 1972-10-16 |
NL7204437A (en) | 1973-10-08 |
FR2178819A1 (en) | 1973-11-16 |
US3824307A (en) | 1974-07-16 |
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