US3281365A - Antiseptic detergent compositions - Google Patents
Antiseptic detergent compositions Download PDFInfo
- Publication number
- US3281365A US3281365A US332945A US33294563A US3281365A US 3281365 A US3281365 A US 3281365A US 332945 A US332945 A US 332945A US 33294563 A US33294563 A US 33294563A US 3281365 A US3281365 A US 3281365A
- Authority
- US
- United States
- Prior art keywords
- detergent
- groups
- phosphonium
- bromide
- soap
- 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
- 239000003599 detergent Substances 0.000 title claims description 58
- 239000000203 mixture Substances 0.000 title claims description 51
- 230000002421 anti-septic effect Effects 0.000 title claims description 18
- -1 PHOSPHONIUM HALIDE Chemical class 0.000 claims description 47
- 239000000344 soap Substances 0.000 claims description 19
- 239000000271 synthetic detergent Substances 0.000 claims description 7
- 239000000022 bacteriostatic agent Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 125000000129 anionic group Chemical group 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 239000002280 amphoteric surfactant Substances 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- WHUHHXPFENAYSA-UHFFFAOYSA-M dodecyl(trimethyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[P+](C)(C)C WHUHHXPFENAYSA-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HVCNMFURAJFOGO-UHFFFAOYSA-N tetradecylphosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC[PH3+] HVCNMFURAJFOGO-UHFFFAOYSA-N 0.000 description 3
- UJHVZVXYELCZLX-UHFFFAOYSA-M tributyl(dodecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC UJHVZVXYELCZLX-UHFFFAOYSA-M 0.000 description 3
- XUNCOSCFGRBTRX-UHFFFAOYSA-M triethyl(octyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CC)(CC)CC XUNCOSCFGRBTRX-UHFFFAOYSA-M 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- UALWTQLGTZXDPC-UHFFFAOYSA-M decyl(triethyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCC[P+](CC)(CC)CC UALWTQLGTZXDPC-UHFFFAOYSA-M 0.000 description 2
- DGNHDBUVMYPHPP-UHFFFAOYSA-M decyl(trimethyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCC[P+](C)(C)C DGNHDBUVMYPHPP-UHFFFAOYSA-M 0.000 description 2
- PQWQRGJUBQOJNL-UHFFFAOYSA-M dodecyl(triethyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[P+](CC)(CC)CC PQWQRGJUBQOJNL-UHFFFAOYSA-M 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- KZTNLWZVGCAPGX-UHFFFAOYSA-N octylphosphanium;chloride Chemical compound [Cl-].CCCCCCCC[PH3+] KZTNLWZVGCAPGX-UHFFFAOYSA-N 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- VCHHWYLEBMBFRZ-UHFFFAOYSA-N tetradecylphosphanium;iodide Chemical compound [I-].CCCCCCCCCCCCCC[PH3+] VCHHWYLEBMBFRZ-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- FUMBGFNGBMYHGH-UHFFFAOYSA-M triphenyl(tetradecyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCCCCCC)C1=CC=CC=C1 FUMBGFNGBMYHGH-UHFFFAOYSA-M 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- DYBIGIADVHIODH-UHFFFAOYSA-N 2-nonylphenol;oxirane Chemical compound C1CO1.CCCCCCCCCC1=CC=CC=C1O DYBIGIADVHIODH-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- GYQBBRRVRKFJRG-UHFFFAOYSA-L disodium pyrophosphate Chemical compound [Na+].[Na+].OP([O-])(=O)OP(O)([O-])=O GYQBBRRVRKFJRG-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- ONQAPBOHQCUFGD-UHFFFAOYSA-N dodecyl ethyl sulfate ethanol Chemical compound S(=O)(=O)(OCCCCCCCCCCCC)OCC.C(C)O.C(C)O ONQAPBOHQCUFGD-UHFFFAOYSA-N 0.000 description 1
- QNALZNMQKPAXNA-UHFFFAOYSA-M dodecyl(trimethyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[P+](C)(C)C QNALZNMQKPAXNA-UHFFFAOYSA-M 0.000 description 1
- YZFCCYBCFQLTKO-UHFFFAOYSA-N dodecylphosphane hydrochloride Chemical compound [Cl-].C(CCCCCCCCCCC)[PH3+] YZFCCYBCFQLTKO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- YYXLGGIKSIZHSF-UHFFFAOYSA-N ethene;furan-2,5-dione Chemical group C=C.O=C1OC(=O)C=C1 YYXLGGIKSIZHSF-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- CSQMFIUTKKRJOX-UHFFFAOYSA-M octadecyl(tripropyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[P+](CCC)(CCC)CCC CSQMFIUTKKRJOX-UHFFFAOYSA-M 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical group P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- FUTRAFMCQUHVQM-UHFFFAOYSA-M tributyl(decyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCC[P+](CCCC)(CCCC)CCCC FUTRAFMCQUHVQM-UHFFFAOYSA-M 0.000 description 1
- ABJGUZZWSKMTEI-UHFFFAOYSA-M tributyl(dodecyl)phosphanium;bromide Chemical group [Br-].CCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC ABJGUZZWSKMTEI-UHFFFAOYSA-M 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- SQJHGFAFGULDEC-UHFFFAOYSA-M tributyl(octadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC SQJHGFAFGULDEC-UHFFFAOYSA-M 0.000 description 1
- YCBRTSYWJMECAH-UHFFFAOYSA-N tributyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC YCBRTSYWJMECAH-UHFFFAOYSA-N 0.000 description 1
- KDNBFSGJXLQPKZ-UHFFFAOYSA-M trimethyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](C)(C)C KDNBFSGJXLQPKZ-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- 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
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/60—Sulfonium or phosphonium compounds
Definitions
- bacteriostatic agents are not effective in preventing or arresting the growth or action of microorganisms such as the Staphylococci, i.e., Staphylococcus aureous, either by inhibiting their activity or by destroying them.
- bacteriostatic agents must be incorporated into the detergent composition to fulfill this function.
- none of the known bacteriostatic agents which are efiective in the presence of detergent compositions aid in the cleansing action and, in fact, some are deleterious to such action.
- a bacteriostatic agent which also exhibits surface active properties and thereby aids the detergent in the cleansing action would represent an advancement in this art.
- R is an aliphatic group containing 6 or more carbon atoms
- R R and R are members selected from the group consisting of aliphatic groups, aryl groups, alkaryl groups, aralkyl groups and alicyclic groups of from 1 to 12 carbon atoms
- X is a member selected from the group consisting of chlorine, bromine and iodine ions
- R represents an aliphatic group containing 6 or more carbon,- atoms
- the group may be a straight chain structure or branched chain structure and may be a saturated group as well as an unsaturated group containing both double and triple bonds, although it is preferred that the group be either an alkyl group or an ethylenically unsaturated group with the group containing from about 8 to 18 carbon atoms.
- R R and R represent groups containing carbon chains, such as aliphatic groups, or groups containing alkyl moieties, i.e., alkaryl groups, such carbon chains may be a straight or branched chain structure.
- R R and R represent groups containing unsaturated carbon chains
- these chains may contain both double bonds and triple bonds as well as contain more than one of such bonds although it is preferred that when such symbols repreent unsaturated carbon chains they are mono-ethylenically unsaturated.
- R R and R represent groups containing aromaticcarbon rings such as aryl groups or groups containing aryl moieties, i.e., alkaryl groups
- such carbon rings are preferably monoor di-ring 3,281,365 Patented Oct. 25, 1966 groups with the mono-ring group being especially preferred.
- the groups represented by R R and R may be like or unlike, it is preferred that each of the groups contain not over about 8 carbon atoms.
- all of the groups represented by R R R and R may contain one or more of the following substituents: hydroxy groups, amino groups, amide groups, ester groups, sulfonyl groups, sulfo groups and nitro groups.
- R is an alkyl group containing from about 8 to 18 carbon atoms; R R and R are lower alkyl groups (l-S carbon atoms) and X is a member selected from the group consisting of bromine and chlorine ions, are particularly effective and especially preferred bacteriostatic agents as well as surface active agents.
- Such compounds include:
- triphenyl oleylphosphonium chloride (2) triethyl heptene-l phosphonium chloride (3) tricyclopentyl dodecylphosphonium chloride (4) tricyclohexyl tetradecylphosphonium bromide (5) tricyclohexyl decylphosphonium bromide (6) triphenyl hexadiene-l,5-phosphonium iodide (7) tribenzyl tetradecylphosphonium bromide 8) tribenzyl dodecylphosphonium chloride 9) tri-isoarnyl oleylphosphonium iodide (10) tri-isopropenyl decylphosphonium bromide (11) tri-p-tolyl heptene-l-phosphonium iodide (12) tri-p-tolyl decylphosphonium chloride (13) trixylyl tetradecylphosphonium bromid
- Example 1 Example 2 In the same manner as indicated in Example 1, about 202 parts of tributyl phosphine and about 205 parts of dodccylchloride were reacted to yield tributyldodecyl phosphonium chloride, a viscous liquid.
- Example 3 In the same manner as indicated in Example 1, about 202 parts of tributyl phosphine and about 273 parts of tetradecyl bromide were reacted to yield tributyl tetradecyl phophonium bromide, a waxy solid (M.P. 37 C.).
- Example 4 In the same manneras indicated in Example 1, about 202 parts of tributyl phosphine and about 297 parts of hexadecyl bromide were reacted to yield tributyl hexadecyl phosphonium bromide, a waxy sOlid (M.P. 55 C.).
- Example 5 In the same manner as indicated in Example 1, about 202 parts of tributyl phosphine and about 321 parts of octadecyl bromide were reacted to yield tributyl octadecyl phosphonium bromide, a waxy solid (M.P. 65 C.).
- Example 6 In the same manner as indicated in Example 1, about 7.6 parts of trimethyl phosphine and about 25 parts of dodecyl bromide were reacted to yield trimethyl dodecyl phosphonium bromide, a white solid (M.P. 193 C.).
- detergent includes soap, i.e., an alkali metal or amine salt of a fatty acid and/or fatty acid mixture, and synthetic detergents, particularly of the anionic, nonionic and amphoteric classes, including mixtures of these.
- antiseptic detergent composition refers to those detergent compositions which are satisfactory detergents and which are effective against Staphylococci.
- the quaternary phosphonium halides of the present invention have been found to not only exhibit surfacetension-reducing properties in aqueous systems but also to exhibit effective bacteriostatic properties in such systems in the presence of detergent compositions.
- the quaternary phosphonium halides of the present invention have been found to not only exhibit surfacetension-reducing properties in aqueous systems but also to exhibit effective bacteriostatic properties in such systems in the presence of detergent compositions.
- quaternary phosphonium chlorides are normally liquids while the bromides are normally solids which permit versatile yet selective methods for formulating with detergent compositions.
- these bacteriostatic agents neither discolor the finished detergent composition nor are irritating to the skin. It is, of course, a distinct advantage of the bacteriostatic agents of the present invention that they additionally aid the detergent composition in its cleansing action by exhibiting surface active properties in aqueous systems.
- the amounts of the quaternary phosphonium halides which are suitable for use in detergent compositions can vary depending upon the end use applications of the detergent composition, such as bar soap, hair shampoo and the like, and, in general, any amount which is antiseptically effective, i.e., effective against Staphylococcus, can be used with amounts below about 50% by weight of the detergent composition being usually acceptable and amounts from about .05% to 10% being preferred. Under some circumstances, some bacteriostatic activity can be found as low as .001% by weight of the detergent.
- the invention is not to be limited to any particular method of preparing the detergent composition containing the bacteriostatic agent.
- the bacteriostatic agent can be mechanically mixed in, crutched in the detergent in the form of a slurry, or dissolved in a solution of the detergent.
- the bacteriostatic agent can be admixed with the detergent in any of the forms in which the detergent is manufactured in, as well as being added simultaneously or separately to an aqueous solution.
- the bacteriostatic agent is intended to be used with the detergent at the time of application as a cleansing agent.
- the resulting antiseptic detergent composition that is, the detergent and the bacteriostatic agent, of the present invention is generally effective when used in aqueous systems in conventional amounts such as is normally used with detergent compositions and which is generally about .2% concentraton or below.
- the following table presents the surface tensions in dynes per centimeter of solutions at the indicated concentrations of these agents and distilled water at 25 C. as determined by the DuNuoy principle using the Fisher tensiomat.
- the surface tension of water is about 72.8 degrees/ cm. at this temperature.
- a reduction of the surface tension of water to about 30 dynes in .25% solution is considered excellent and if this reduction is maintained practically unchanged to a dilution as low as .05%, the material is considered an extremely active surface-tension-reducing agent.
- the bacteriostatic agents of the present invention are effective in controlling bacterial growth in the presence of detergents such as an Ivory brand neutral high grade toilet soap which is a mixture of alkali metal salts of fatty acids analyzing about 46 weight percent oleic and linoleic acid, about 14 weight percent stearic acid, about 30 weight percent palmitic acid and about 10 weight percent of lower fatty acids (myristic, lauric, etc.), and when incorporated in such a soap ina weight ratio of one part to 50 parts soap are effective in low concentrations (from about 1 to p.p.m.) against an inoculum of a standard culture of Micrococcus pyogenes var. aureus (Staphylococcus aureus) of standard resistance in a Sabourards dextrose agar medium.
- detergents such as an Ivory brand neutral high grade toilet soap which is a mixture of alkali metal salts of fatty acids analyzing about 46 weight percent oleic and lin
- Comparable effectiveness can also be obtained when using other soaps such as a Lux brand solid neutral white toilet soap (a mixture of alkali metal salts of fatty acids whose fatty acid content analyzes about 45% oleic and linoleic, about 30% palmitic acid, about 10% stearic acid and about 15% lower fatty acids) as well as anionic, nonionic and amphoteric synthetic detergents.
- Anionic surface active compounds can be broadly described as compounds which contain hydrophilic and lyophilic groups in their molecular structure and which ionize in an aqueous medium to give anions containing the lyophilic group.
- These compounds are usually the alkali metal salts of organic sulfonates or sulfates, particularly the sodium salts, such as alkyl aryl sulfonates (e.g. sodium dodecyl benzene sulfonate), sulfate of straight chain primary alcohols (e.g., sodium lauryl sulfate) and the like.
- alkyl aryl sulfonates e.g. sodium dodecyl benzene sulfonate
- sulfate of straight chain primary alcohols e.g., sodium lauryl sulfate
- Nonionic surface active compounds can be broadly described as compounds which do not ionize but acquire hydrophilic characteristics from an oxygenated side chain, usually polyoxyethylene, while the lyophilic part of the molecule may come from fatty acids, phenols, alcohols, amides or amines.
- the polyethylene oxide condensates of alkyl phenols e.g., condensation product formed from 1 mole nonyl phenol and moles ethylene oxide
- the condensation products of aliphatic alcohols and ethylene oxide e.g. condensation product formed from 1 mole tridecanol and 12 moles ethylene oxide
- Amphoteric surface active compounds can be broadly described as compounds which have both anionic and cationic groups in the same molecule. Examples of such compounds include sodium N-methyl taurate and sodium N-coco beta amino propionate.
- a detergent composition of the present invention need contain only a detergent and the quaternary phosphonium halide, it will be appreciated that the incorporation in the mixture of additional ingredients commonly used with cleansing agents, such as perfume, builders (e.g., sodium tripolyphosphate) anti-redeposition agents (e.g., carboxymethylcellulose), brightening agents (e.g., fluorescent dyes) and the like, is contemplated as being within the invention.
- cleansing agents such as perfume, builders (e.g., sodium tripolyphosphate) anti-redeposition agents (e.g., carboxymethylcellulose), brightening agents (e.g., fluorescent dyes) and the like, is contemplated as being within the invention.
- Example 7 A detergent composition is prepared formulated as follows:
- the above composition is prepared by melting the soap in a suitable vessel at about 60 to 70 C. and adding the phosphonium bromide to the soap with agitation. The admixture is then poured into a suitable mold and allowed to solidify by cooling to room temperature (about 25 C).
- Example 8 A liquid detergent composition is prepared formuulated as follows:
- Nonionic organic active nonyl phenol-ethylene oxide condensate
- Maleic anhydride-ethylene copolymer 1.0
- Tetrapotassium pyrophosphate 20.0
- Potassium hydroxide 45% by Weight
- Sodium silicate Na O:SiO of 1:2
- the above composition is prepared by heating the water to about 60 C. and thereafter adding the above additives to the water in a mixer in their above listed order, each additive being added and mixed under high shear agitation over a period of about 1 to about 7 minutes while ensuring that the temperature of the mix does not exceed about 80 C.
- Example 9 An antiseptic shampoo composition is prepared formulated sa follows:
- the above composition is prepared by melting the potassium stearate at about 60 to 70 C. and adding thereto the triethanol lauryl sulfate, methyl cellulose, propylene glycol and tributyl tetradecyl phosphonium cholride until the mixture is well mixed and blended and thereafter adding the water in such a manner as to prevent aeration.
- An antiseptic detergent composition consisting essentially of a detergent selected from the class consisting of soap and organic synthetic detergents selected from the class consisting of non-soap anionic, nonionic and amphoteric surfactants and at least an antiseptically eitective amount of a quaternary phosphonium halide of the following formula wherein R is an aliphtic group containing from 6 to 24 carbon atoms; R R and R are members selected from the group consisting of aliphatic groups, aryl groups, alkaryl groups, aralkyl groups, and alicyclic groups of from 1 to 12 carbon atoms; and X is a member selected from the group consisting of chlormine, bromine, and iodine ions.
- An antiseptic detergent composition consisting essentially of a detergent selected from the class consisting of soap and organic synthetic detergents selected from the class consisting of non-soap anionic, nonionic and amphoteric surfactants and at least an antiseptically effective amount of an unsymmetrical tetra alkyl phosphonium halide of the following formula wherein R is an alkyl group containing from about 8 to 18 carbon atoms; R R and R are lower alkyl groups containing from 1 to 5 carbon atoms and X is a member selected from the group consisting of bromine and chlorine ions.
- an antiseptic detergent composition according to claim 6, wherein said detergent is an organic synthetic detergent selected from the class consisting of non-soap anionic, nonionic and amphoteric surfactants.
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Description
United States Patent 3,281,365 ANTISEPTIC DETERGENT COMPOSITIONS Kurt Moedritzer, Webster Groves, Mo., assignor to Monsanto Company, a corporation of Delaware No Drawing. Filed Dec. 23, 1963, Ser. No. 332,945 11 Claims. (Cl. 252-107) This invention relates to new and novel detergent compositions and more particularly to detergent compositions containing a bacteriostatic agent.
Detergents of themselves are not effective in preventing or arresting the growth or action of microorganisms such as the Staphylococci, i.e., Staphylococcus aureous, either by inhibiting their activity or by destroying them. Thus, when such action is desired bacteriostatic agents must be incorporated into the detergent composition to fulfill this function. However, none of the known bacteriostatic agents which are efiective in the presence of detergent compositions aid in the cleansing action and, in fact, some are deleterious to such action. As can be appreciated, therefore, a bacteriostatic agent which also exhibits surface active properties and thereby aids the detergent in the cleansing action would represent an advancement in this art.
It is, therefore, an object of this invention to provide improved antiseptic detergent compositions.
It is a further object of this invention to provide detergent compositions having incorporated therein a bacteriostatic agent which exhibits surface active properties.
Other objects will become apparent from a reading of the following detailed description and the claims appended hereto.
It has been found that quaternary phosphonium halides of the following formula wherein R is an aliphatic group containing 6 or more carbon atoms; R R and R are members selected from the group consisting of aliphatic groups, aryl groups, alkaryl groups, aralkyl groups and alicyclic groups of from 1 to 12 carbon atoms; and X is a member selected from the group consisting of chlorine, bromine and iodine ions, unexpectedly exhibit bacteriostatic properties as well as surface active properties as will be more fully discussed hereinafter.
In the foregoing general Formula 1 wherein R represents an aliphatic group containing 6 or more carbon,- atoms, it is preferred that the group contain not over about 24 carbon atoms and the group may be a straight chain structure or branched chain structure and may be a saturated group as well as an unsaturated group containing both double and triple bonds, although it is preferred that the group be either an alkyl group or an ethylenically unsaturated group with the group containing from about 8 to 18 carbon atoms. When the symbols R R and R represent groups containing carbon chains, such as aliphatic groups, or groups containing alkyl moieties, i.e., alkaryl groups, such carbon chains may be a straight or branched chain structure. When the symbols R R and R represent groups containing unsaturated carbon chains, these chains may contain both double bonds and triple bonds as well as contain more than one of such bonds although it is preferred that when such symbols repreent unsaturated carbon chains they are mono-ethylenically unsaturated. When the symbols R R and R represent groups containing aromaticcarbon rings such as aryl groups or groups containing aryl moieties, i.e., alkaryl groups, such carbon rings are preferably monoor di-ring 3,281,365 Patented Oct. 25, 1966 groups with the mono-ring group being especially preferred. Although the groups represented by R R and R may be like or unlike, it is preferred that each of the groups contain not over about 8 carbon atoms. In addition, all of the groups represented by R R R and R may contain one or more of the following substituents: hydroxy groups, amino groups, amide groups, ester groups, sulfonyl groups, sulfo groups and nitro groups.
It has been found that the unsymmetrical tetraalkyl phosphonium halides of the following formula:
wherein R is an alkyl group containing from about 8 to 18 carbon atoms; R R and R are lower alkyl groups (l-S carbon atoms) and X is a member selected from the group consisting of bromine and chlorine ions, are particularly effective and especially preferred bacteriostatic agents as well as surface active agents.
Such compounds include:
( 1) trimethyl dodecyl phosphonium chloride (2) triethyl octylphosphonium bromide (3) trimethyl tetradecyl phosphonium chloride (4) tri-n-propyl octadecyl phosphonium bromide (5) tri-n-amyl decyl phosphonium chloride (6) triethyl decyl phosphonium chloride (7) trimethyl decyl phosphonium bromide (8) triethyl dodecyl phosphonium chloride (9) tri-isopropyl tetradecyl phosphonium bromide (10) tri-n-butyl decyl phosphonium chloride Examples of compounds other than of the preferred class described above which can be employed in :accordance with this invention include:
(1) triphenyl oleylphosphonium chloride (2) triethyl heptene-l phosphonium chloride (3) tricyclopentyl dodecylphosphonium chloride (4) tricyclohexyl tetradecylphosphonium bromide (5) tricyclohexyl decylphosphonium bromide (6) triphenyl hexadiene-l,5-phosphonium iodide (7) tribenzyl tetradecylphosphonium bromide 8) tribenzyl dodecylphosphonium chloride 9) tri-isoarnyl oleylphosphonium iodide (10) tri-isopropenyl decylphosphonium bromide (11) tri-p-tolyl heptene-l-phosphonium iodide (12) tri-p-tolyl decylphosphonium chloride (13) trixylyl tetradecylphosphonium bromide (14) tri-isobutenyl tetradecylphosphoniorn chloride (15) tripropenyl tetradecylphosphonium iodide (16) tri-n-butenyl decylphosphonium iodide (17) tri-isopropenyl hexadecylphosphonium iodide (18) triphenyl tetradecylphosphonium bromide (19) tribenzyl octylphosphonium chloride (20) tricyclohexyl octadecylphosphonium bromide The quaternary phosphonium halides of the present inventiou can be prepared by many various methods which include reacting in an inert atmosphere a triorgano phosphine with an aliphatic halide at temperatures of from about C. to about C. for a period of a few hours. The following is the reaction in equation form:
wherein the groups R R R R and X are the same as represented in the foregoing general Formula 1.
3 The following examples are presented to illustrate the invention, with parts by weight being used in the examples unles otherwie indicated.
Example 1 Example 2 In the same manner as indicated in Example 1, about 202 parts of tributyl phosphine and about 205 parts of dodccylchloride were reacted to yield tributyldodecyl phosphonium chloride, a viscous liquid.
Example 3 In the same manner as indicated in Example 1, about 202 parts of tributyl phosphine and about 273 parts of tetradecyl bromide were reacted to yield tributyl tetradecyl phophonium bromide, a waxy solid (M.P. 37 C.).
Example 4 In the same manneras indicated in Example 1, about 202 parts of tributyl phosphine and about 297 parts of hexadecyl bromide were reacted to yield tributyl hexadecyl phosphonium bromide, a waxy sOlid (M.P. 55 C.).
Example 5 In the same manner as indicated in Example 1, about 202 parts of tributyl phosphine and about 321 parts of octadecyl bromide were reacted to yield tributyl octadecyl phosphonium bromide, a waxy solid (M.P. 65 C.).
Example 6 In the same manner as indicated in Example 1, about 7.6 parts of trimethyl phosphine and about 25 parts of dodecyl bromide were reacted to yield trimethyl dodecyl phosphonium bromide, a white solid (M.P. 193 C.).
The term detergent includes soap, i.e., an alkali metal or amine salt of a fatty acid and/or fatty acid mixture, and synthetic detergents, particularly of the anionic, nonionic and amphoteric classes, including mixtures of these. The term antiseptic detergent composition refers to those detergent compositions which are satisfactory detergents and which are effective against Staphylococci.
The quaternary phosphonium halides of the present invention have been found to not only exhibit surfacetension-reducing properties in aqueous systems but also to exhibit effective bacteriostatic properties in such systems in the presence of detergent compositions. In general,
. quaternary phosphonium chlorides are normally liquids while the bromides are normally solids which permit versatile yet selective methods for formulating with detergent compositions. In addition, these bacteriostatic agents neither discolor the finished detergent composition nor are irritating to the skin. It is, of course, a distinct advantage of the bacteriostatic agents of the present invention that they additionally aid the detergent composition in its cleansing action by exhibiting surface active properties in aqueous systems.
The amounts of the quaternary phosphonium halides which are suitable for use in detergent compositions can vary depending upon the end use applications of the detergent composition, such as bar soap, hair shampoo and the like, and, in general, any amount which is antiseptically effective, i.e., effective against Staphylococcus, can be used with amounts below about 50% by weight of the detergent composition being usually acceptable and amounts from about .05% to 10% being preferred. Under some circumstances, some bacteriostatic activity can be found as low as .001% by weight of the detergent.
The invention is not to be limited to any particular method of preparing the detergent composition containing the bacteriostatic agent. The bacteriostatic agent can be mechanically mixed in, crutched in the detergent in the form of a slurry, or dissolved in a solution of the detergent. In addition, the bacteriostatic agent can be admixed with the detergent in any of the forms in which the detergent is manufactured in, as well as being added simultaneously or separately to an aqueous solution. In any event, the bacteriostatic agent is intended to be used with the detergent at the time of application as a cleansing agent.
The resulting antiseptic detergent composition, that is, the detergent and the bacteriostatic agent, of the present invention is generally effective when used in aqueous systems in conventional amounts such as is normally used with detergent compositions and which is generally about .2% concentraton or below.
In order to illustrate the surface active properties of the bacteriotsatic agents of the instant invention, the following table presents the surface tensions in dynes per centimeter of solutions at the indicated concentrations of these agents and distilled water at 25 C. as determined by the DuNuoy principle using the Fisher tensiomat. The surface tension of water is about 72.8 degrees/ cm. at this temperature. A reduction of the surface tension of water to about 30 dynes in .25% solution is considered excellent and if this reduction is maintained practically unchanged to a dilution as low as .05%, the material is considered an extremely active surface-tension-reducing agent.
As previously mentioned, the bacteriostatic agents of the present invention are effective in controlling bacterial growth in the presence of detergents such as an Ivory brand neutral high grade toilet soap which is a mixture of alkali metal salts of fatty acids analyzing about 46 weight percent oleic and linoleic acid, about 14 weight percent stearic acid, about 30 weight percent palmitic acid and about 10 weight percent of lower fatty acids (myristic, lauric, etc.), and when incorporated in such a soap ina weight ratio of one part to 50 parts soap are effective in low concentrations (from about 1 to p.p.m.) against an inoculum of a standard culture of Micrococcus pyogenes var. aureus (Staphylococcus aureus) of standard resistance in a Sabourards dextrose agar medium.
Comparable effectiveness can also be obtained when using other soaps such as a Lux brand solid neutral white toilet soap (a mixture of alkali metal salts of fatty acids whose fatty acid content analyzes about 45% oleic and linoleic, about 30% palmitic acid, about 10% stearic acid and about 15% lower fatty acids) as well as anionic, nonionic and amphoteric synthetic detergents. Anionic surface active compounds can be broadly described as compounds which contain hydrophilic and lyophilic groups in their molecular structure and which ionize in an aqueous medium to give anions containing the lyophilic group. These compounds are usually the alkali metal salts of organic sulfonates or sulfates, particularly the sodium salts, such as alkyl aryl sulfonates (e.g. sodium dodecyl benzene sulfonate), sulfate of straight chain primary alcohols (e.g., sodium lauryl sulfate) and the like. Nonionic surface active compounds can be broadly described as compounds which do not ionize but acquire hydrophilic characteristics from an oxygenated side chain, usually polyoxyethylene, while the lyophilic part of the molecule may come from fatty acids, phenols, alcohols, amides or amines. For example purposes only, the polyethylene oxide condensates of alkyl phenols (e.g., condensation product formed from 1 mole nonyl phenol and moles ethylene oxide), the condensation products of aliphatic alcohols and ethylene oxide (e.g. condensation product formed from 1 mole tridecanol and 12 moles ethylene oxide) are suitable nonionic surface active compounds in practicing the invention. Amphoteric surface active compounds can be broadly described as compounds which have both anionic and cationic groups in the same molecule. Examples of such compounds include sodium N-methyl taurate and sodium N-coco beta amino propionate.
While a detergent composition of the present invention need contain only a detergent and the quaternary phosphonium halide, it will be appreciated that the incorporation in the mixture of additional ingredients commonly used with cleansing agents, such as perfume, builders (e.g., sodium tripolyphosphate) anti-redeposition agents (e.g., carboxymethylcellulose), brightening agents (e.g., fluorescent dyes) and the like, is contemplated as being within the invention.
A further understanding of the detergent compositions described herein and processes for preparing the compositions will be obtained from the following specific examples which are intended to illustrate this invention, but not to limit the scope thereof, parts and percentages being by weight unless otherwise indicated.
Example 7 A detergent composition is prepared formulated as follows:
Parts The above composition is prepared by melting the soap in a suitable vessel at about 60 to 70 C. and adding the phosphonium bromide to the soap with agitation. The admixture is then poured into a suitable mold and allowed to solidify by cooling to room temperature (about 25 C).
Example 8 A liquid detergent composition is prepared formuulated as follows:
Additive: Parts Water 46.1 Sodium carboxymethyl cellulose (95% by weight) .5 Fluorescent dye .025 Disodium acid pyrophosphate 5.0
Nonionic organic active (nonyl phenol-ethylene oxide condensate) 10.0 Maleic anhydride-ethylene copolymer 1.0 Tetrapotassium pyrophosphate 20.0 Potassium hydroxide (45% by Weight) 6.7 Sodium silicate (Na O:SiO of 1:2) (44.1%
by weight) 10.0
Tributyl dodecyl phosphonium chloride 1.0
The above composition is prepared by heating the water to about 60 C. and thereafter adding the above additives to the water in a mixer in their above listed order, each additive being added and mixed under high shear agitation over a period of about 1 to about 7 minutes while ensuring that the temperature of the mix does not exceed about 80 C.
6 Example 9 An antiseptic shampoo composition is prepared formulated sa follows:
The above composition is prepared by melting the potassium stearate at about 60 to 70 C. and adding thereto the triethanol lauryl sulfate, methyl cellulose, propylene glycol and tributyl tetradecyl phosphonium cholride until the mixture is well mixed and blended and thereafter adding the water in such a manner as to prevent aeration.
What is claimed is:
1. An antiseptic detergent composition consisting essentially of a detergent selected from the class consisting of soap and organic synthetic detergents selected from the class consisting of non-soap anionic, nonionic and amphoteric surfactants and at least an antiseptically eitective amount of a quaternary phosphonium halide of the following formula wherein R is an aliphtic group containing from 6 to 24 carbon atoms; R R and R are members selected from the group consisting of aliphatic groups, aryl groups, alkaryl groups, aralkyl groups, and alicyclic groups of from 1 to 12 carbon atoms; and X is a member selected from the group consisting of chlormine, bromine, and iodine ions.
2. An antiseptic detergent composition according to claim 1, wherein said quaternary phosphonium halide is present in amounts below about 50% by weight of said compositions.
3. An antiseptic detergent composition according to claim 2, wherein said detergent is soap.
4. An antiseptic detergent composition according to claim 2, wherein said detergent is an organic synthetic detergent selected from the class consisting of non-soap anionic, nonionic and amphoteric surfactants.
5. An antiseptic detergent composition consisting essentially of a detergent selected from the class consisting of soap and organic synthetic detergents selected from the class consisting of non-soap anionic, nonionic and amphoteric surfactants and at least an antiseptically effective amount of an unsymmetrical tetra alkyl phosphonium halide of the following formula wherein R is an alkyl group containing from about 8 to 18 carbon atoms; R R and R are lower alkyl groups containing from 1 to 5 carbon atoms and X is a member selected from the group consisting of bromine and chlorine ions.
6. An antiseptic detergent composition according to claim 5, wherein said unsymmetrical quaternary alkyl phosphonium halide is present in amounts below about 50% by weight of said composition.
7. An antiseptic detergent composition according to claim 6, wherein said detergent is soap.
8. An antiseptic detergent composition according to claim 6, wherein said detergent is an organic synthetic detergent selected from the class consisting of non-soap anionic, nonionic and amphoteric surfactants.
9. An antiseptic detergent composition according to claim 5, wherein said unsymmetrical tetra alkyl phosphonium halide is present in amounts from about .05% to about 10% by weight of said composition.
10. An antiseptic detergent composition according to claim 9, wherein said unsymmetrical tetra alkyl phosphonium halide is tributyl dodecyl phosphonium chloride.
11. An antiseptic detergent composition according to claim 9, wherein said unsymmetrical tetra alkyl phosphonium halide is tributyl dodecyl phosphonium bromide.
References Cited by the Examiner UNITED STATES PATENTS 1,921,364 8/1933 Lommel et a1. 2,265,759 12/ 1941 Lawton et a1. 2,577,773 12/1951 Lambert 252107 XR 2,950,255 8/1960 Golf 252106 XR 3,141,821 7/1964 Compeau 252-106 XR LEON D. ROSDOL, Primary Examiner.
JULIUS GREENWALD, W. E. SCHULZ,
Assistant Examiners.
Claims (1)
1. AN ANTISEPTIC DETERGENT COMPOSITION CONSISTING ESSENTIALLY OF A DETERGENT SELECTED FROM THE CLASS CONSISTING OF SOAP AND ORGANIC SYNTHETIC DETERGENTS SELECTED FROM THE CLASS CONSISTING OF NON-SOAP ANIONIC, NONIONIC AND AMPHOTERIC SULFACTANTS AND AT LEAST AN ANTISEPTICALLY EFFECTIVE AMOUNT OF A QUATERNARY PHOSPHONIUM HALIDE OF THE FOLLOWING FORMULA
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US4188380A (en) * | 1974-07-31 | 1980-02-12 | Exxon Research & Engineering Co. | Surface active quaternary higher dialkyl phosphonium salt biocides and intermediates |
EP0066544A1 (en) * | 1981-05-30 | 1982-12-08 | Ciba-Geigy Ag | Water treatment |
US4673509A (en) * | 1983-08-26 | 1987-06-16 | Albright & Wilson Limited | Biocidal water treatment |
BE1003510A5 (en) * | 1989-10-09 | 1992-04-07 | Fabricom Air Conditioning Sa | DISINFECTANT COMPOSITION AND DISINFECTION METHOD. |
EP0544619A1 (en) * | 1991-11-27 | 1993-06-02 | Ciba-Geigy Ag | Protection of non-aqueous systems with biocides |
EP0549006A2 (en) * | 1991-11-27 | 1993-06-30 | Fmc Corporation (Uk) Limited | Ammonium and phosphonium salts and their use as biocides |
EP0959122A1 (en) * | 1998-05-18 | 1999-11-24 | Bayer Corporation | Cleaning solution for optical surfaces of urine analyzers |
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JP2007238537A (en) * | 2006-03-10 | 2007-09-20 | K I Chemical Industry Co Ltd | Additive for circulating water in coating booth, method for treating water and circulating water for coating booth |
US20100226874A1 (en) * | 2009-03-06 | 2010-09-09 | Jeffrey Kramer | Biocidal compositions |
FR2955488A1 (en) * | 2010-01-28 | 2011-07-29 | Oreal | Composition, useful for dyeing human keratin fibers, preferably hair, comprises one or more hair dye, and at least one quaternary phosphonium hydroxide in a medium |
US20120048809A1 (en) * | 2010-08-31 | 2012-03-01 | Riggs Jr Olen L | Chemicals for Oil Spill Cleanup |
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US9694021B2 (en) | 2010-04-28 | 2017-07-04 | Alcon Research, Ltd | Pharmaceutical compositions with phosphonium antimicrobial agents |
US9957173B2 (en) | 2015-10-08 | 2018-05-01 | Bwa Water Additives Uk Limited | Treatment of water |
US10004233B2 (en) | 2015-10-01 | 2018-06-26 | Bwa Water Additives Uk Limited | Relating to treatment of water |
US10214684B2 (en) | 2015-09-30 | 2019-02-26 | Bwa Water Additives Uk Limited | Friction reducers and well treatment fluids |
US10538442B2 (en) | 2015-08-31 | 2020-01-21 | Bwa Water Additives Uk Limited | Water treatment |
US10570033B2 (en) | 2016-05-12 | 2020-02-25 | Italmatch Chemicals Gb Limited | Water treatment |
US10827758B2 (en) | 2014-10-14 | 2020-11-10 | Italmatch Chemicals Gb Limited | Relating to water treatment |
US10905125B2 (en) | 2014-10-14 | 2021-02-02 | Italmatch Chemicals Gb Ltd. | Biocidal compositions and method of treating water using thereof |
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Cited By (27)
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US4188380A (en) * | 1974-07-31 | 1980-02-12 | Exxon Research & Engineering Co. | Surface active quaternary higher dialkyl phosphonium salt biocides and intermediates |
EP0066544A1 (en) * | 1981-05-30 | 1982-12-08 | Ciba-Geigy Ag | Water treatment |
US4874526A (en) * | 1981-05-30 | 1989-10-17 | Ciba-Geigy Corporation | Treatment of water |
US4673509A (en) * | 1983-08-26 | 1987-06-16 | Albright & Wilson Limited | Biocidal water treatment |
BE1003510A5 (en) * | 1989-10-09 | 1992-04-07 | Fabricom Air Conditioning Sa | DISINFECTANT COMPOSITION AND DISINFECTION METHOD. |
EP0549006A2 (en) * | 1991-11-27 | 1993-06-30 | Fmc Corporation (Uk) Limited | Ammonium and phosphonium salts and their use as biocides |
EP0549006A3 (en) * | 1991-11-27 | 1994-07-13 | Fmc Corp Uk Ltd | Ammonium and phosphonium salts and their use as biocides |
EP0544619A1 (en) * | 1991-11-27 | 1993-06-02 | Ciba-Geigy Ag | Protection of non-aqueous systems with biocides |
EP0959122A1 (en) * | 1998-05-18 | 1999-11-24 | Bayer Corporation | Cleaning solution for optical surfaces of urine analyzers |
CN1111165C (en) * | 2000-05-15 | 2003-06-11 | 南京化工大学 | Aldehyde acetal modified quaternary phosphate and its preparing method and use |
JP2007238537A (en) * | 2006-03-10 | 2007-09-20 | K I Chemical Industry Co Ltd | Additive for circulating water in coating booth, method for treating water and circulating water for coating booth |
US10480125B2 (en) * | 2009-03-06 | 2019-11-19 | Bwa Water Additives Uk Limited | Biocidal compositions |
US20100226874A1 (en) * | 2009-03-06 | 2010-09-09 | Jeffrey Kramer | Biocidal compositions |
FR2955488A1 (en) * | 2010-01-28 | 2011-07-29 | Oreal | Composition, useful for dyeing human keratin fibers, preferably hair, comprises one or more hair dye, and at least one quaternary phosphonium hydroxide in a medium |
EP2359804A3 (en) * | 2010-01-28 | 2015-08-05 | L'Oréal | Composition including an oxidation dye and a derivative of phosphonium or ammonium hydroxide, dyeing of keratin fibres and device |
US9694021B2 (en) | 2010-04-28 | 2017-07-04 | Alcon Research, Ltd | Pharmaceutical compositions with phosphonium antimicrobial agents |
US20120048809A1 (en) * | 2010-08-31 | 2012-03-01 | Riggs Jr Olen L | Chemicals for Oil Spill Cleanup |
US8936728B2 (en) * | 2010-08-31 | 2015-01-20 | Debra A. Riggs | Chemicals for oil spill cleanup |
US10827758B2 (en) | 2014-10-14 | 2020-11-10 | Italmatch Chemicals Gb Limited | Relating to water treatment |
US10905125B2 (en) | 2014-10-14 | 2021-02-02 | Italmatch Chemicals Gb Ltd. | Biocidal compositions and method of treating water using thereof |
US10538442B2 (en) | 2015-08-31 | 2020-01-21 | Bwa Water Additives Uk Limited | Water treatment |
US10214684B2 (en) | 2015-09-30 | 2019-02-26 | Bwa Water Additives Uk Limited | Friction reducers and well treatment fluids |
US11814582B2 (en) | 2015-09-30 | 2023-11-14 | Italmatch Chemicals Gb Limited | Friction reducers and well treatment fluids |
US10004233B2 (en) | 2015-10-01 | 2018-06-26 | Bwa Water Additives Uk Limited | Relating to treatment of water |
US9957173B2 (en) | 2015-10-08 | 2018-05-01 | Bwa Water Additives Uk Limited | Treatment of water |
US10570033B2 (en) | 2016-05-12 | 2020-02-25 | Italmatch Chemicals Gb Limited | Water treatment |
US11691898B2 (en) | 2016-05-12 | 2023-07-04 | Italmatch Chemicals Gb Limited | Water treatment |
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