US3507937A - Reversed zwitterionic phosphorus compounds - Google Patents
Reversed zwitterionic phosphorus compounds Download PDFInfo
- Publication number
- US3507937A US3507937A US584099A US3507937DA US3507937A US 3507937 A US3507937 A US 3507937A US 584099 A US584099 A US 584099A US 3507937D A US3507937D A US 3507937DA US 3507937 A US3507937 A US 3507937A
- Authority
- US
- United States
- Prior art keywords
- methyl
- sodium
- ethyl
- compounds
- reversed
- 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
- 150000003018 phosphorus compounds Chemical class 0.000 title 1
- -1 alkyl or alkenyl Chemical class 0.000 description 65
- 239000000203 mixture Substances 0.000 description 63
- 150000001875 compounds Chemical class 0.000 description 60
- 229910052739 hydrogen Inorganic materials 0.000 description 37
- 239000001257 hydrogen Substances 0.000 description 37
- 239000003599 detergent Substances 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 35
- 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 28
- 239000011734 sodium Substances 0.000 description 27
- 235000015424 sodium Nutrition 0.000 description 27
- 229910052708 sodium Inorganic materials 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 229910019142 PO4 Inorganic materials 0.000 description 13
- 150000002431 hydrogen Chemical class 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- 235000021317 phosphate Nutrition 0.000 description 13
- 239000010452 phosphate Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 125000000129 anionic group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 9
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 235000007686 potassium Nutrition 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 235000019832 sodium triphosphate Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000004115 Sodium Silicate Substances 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 159000000001 potassium salts Chemical class 0.000 description 5
- 239000003352 sequestering agent Substances 0.000 description 5
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 5
- 229910052911 sodium silicate Inorganic materials 0.000 description 5
- 239000003760 tallow Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- PKYJSCBBIZGCSJ-UHFFFAOYSA-N CCCCCCCCCCCCP(O)=O Chemical compound CCCCCCCCCCCCP(O)=O PKYJSCBBIZGCSJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000012669 liquid formulation Substances 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- IGLCXPLHWRWSMO-UHFFFAOYSA-N 1-dichlorophosphoryldodecane Chemical compound CCCCCCCCCCCCP(Cl)(Cl)=O IGLCXPLHWRWSMO-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- RFFZIJDMUINRBG-UHFFFAOYSA-N P([O-])([O-])=O.[NH4+].C=C.[NH4+] Chemical compound P([O-])([O-])=O.[NH4+].C=C.[NH4+] RFFZIJDMUINRBG-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 2
- UTAKXKIFBMWPQS-UHFFFAOYSA-N dodecyl-[2-(trimethylazaniumyl)ethoxy]phosphinate Chemical compound CCCCCCCCCCCCP([O-])(=O)OCC[N+](C)(C)C UTAKXKIFBMWPQS-UHFFFAOYSA-N 0.000 description 2
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229920005646 polycarboxylate Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 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
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
- 239000000271 synthetic detergent Substances 0.000 description 2
- 239000007916 tablet composition Substances 0.000 description 2
- 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 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OGTPNDHOHCFDTK-UHFFFAOYSA-N 1,2,3-triphosphonopropan-2-ylphosphonic acid Chemical compound OP(O)(=O)CC(P(O)(O)=O)(P(O)(O)=O)CP(O)(O)=O OGTPNDHOHCFDTK-UHFFFAOYSA-N 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical class CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- OJLFRYBHGVWGJN-UHFFFAOYSA-N 1-[hexadecyl(dimethyl)azaniumyl]-2-hydroxypropane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C(C(C)O)S([O-])(=O)=O OJLFRYBHGVWGJN-UHFFFAOYSA-N 0.000 description 1
- NVIKEGBHOVMMDC-UHFFFAOYSA-N 1-dichlorophosphoryloxydodecane Chemical compound CCCCCCCCCCCCOP(Cl)(Cl)=O NVIKEGBHOVMMDC-UHFFFAOYSA-N 0.000 description 1
- CJPDBKNETSCHCH-UHFFFAOYSA-N 1-methylsulfinyldodecane Chemical compound CCCCCCCCCCCCS(C)=O CJPDBKNETSCHCH-UHFFFAOYSA-N 0.000 description 1
- MZQKADNPDLDGJD-UHFFFAOYSA-N 2,3,4,5-tetrapropylbenzenesulfonic acid Chemical compound CCCC1=CC(S(O)(=O)=O)=C(CCC)C(CCC)=C1CCC MZQKADNPDLDGJD-UHFFFAOYSA-N 0.000 description 1
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 1
- XYJLPCAKKYOLGU-UHFFFAOYSA-N 2-phosphonoethylphosphonic acid Chemical class OP(O)(=O)CCP(O)(O)=O XYJLPCAKKYOLGU-UHFFFAOYSA-N 0.000 description 1
- MZPBGKHCHOCSOL-UHFFFAOYSA-N 3-(dodecylamino)propanoic acid;sodium Chemical compound [Na].CCCCCCCCCCCCNCCC(O)=O MZPBGKHCHOCSOL-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- AWCRUZMIVIVPCB-UHFFFAOYSA-N CC.[Na].[Na].[Na] Chemical compound CC.[Na].[Na].[Na] AWCRUZMIVIVPCB-UHFFFAOYSA-N 0.000 description 1
- MGJJRXIEFROZLZ-UHFFFAOYSA-N CCCCCCCCCCCCOP(O)=O Chemical compound CCCCCCCCCCCCOP(O)=O MGJJRXIEFROZLZ-UHFFFAOYSA-N 0.000 description 1
- KVKBIUIRUWAULK-UHFFFAOYSA-N CCCCCCCCCCCCP(=O)(O)OCCC Chemical compound CCCCCCCCCCCCP(=O)(O)OCCC KVKBIUIRUWAULK-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical class OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 1
- ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- FENRSEGZMITUEF-ATTCVCFYSA-E [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].OP(=O)([O-])O[C@@H]1[C@@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H]1OP(=O)([O-])[O-] Chemical class [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].OP(=O)([O-])O[C@@H]1[C@@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H]1OP(=O)([O-])[O-] FENRSEGZMITUEF-ATTCVCFYSA-E 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GMSWRMUHJLKEIL-UHFFFAOYSA-N azane;ethene Chemical compound N.C=C GMSWRMUHJLKEIL-UHFFFAOYSA-N 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- TVMVXMQYKSXBJC-UHFFFAOYSA-M dodecyl(ethoxy)phosphinate Chemical compound CCCCCCCCCCCCP([O-])(=O)OCC TVMVXMQYKSXBJC-UHFFFAOYSA-M 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- QBHFVMDLPTZDOI-UHFFFAOYSA-N dodecylphosphocholine Chemical compound CCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C QBHFVMDLPTZDOI-UHFFFAOYSA-N 0.000 description 1
- SVMUEEINWGBIPD-UHFFFAOYSA-N dodecylphosphonic acid Chemical compound CCCCCCCCCCCCP(O)(O)=O SVMUEEINWGBIPD-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- IZWSFJTYBVKZNK-UHFFFAOYSA-N lauryl sulfobetaine Chemical compound CCCCCCCCCCCC[N+](C)(C)CCCS([O-])(=O)=O IZWSFJTYBVKZNK-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical class OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- HXZSFRJGDPGVNY-UHFFFAOYSA-N methyl(oxido)phosphanium Chemical compound C[PH2]=O HXZSFRJGDPGVNY-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- LTUGGBOPBQPPGK-UHFFFAOYSA-A octadecasodium;hexaphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LTUGGBOPBQPPGK-UHFFFAOYSA-A 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- HJZKOAYDRQLPME-UHFFFAOYSA-N oxidronic acid Chemical compound OP(=O)(O)C(O)P(O)(O)=O HJZKOAYDRQLPME-UHFFFAOYSA-N 0.000 description 1
- 229960004230 oxidronic acid Drugs 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- XYORSKKUGAGNPC-UHFFFAOYSA-N phosphonocarbonylphosphonic acid Chemical compound OP(O)(=O)C(=O)P(O)(O)=O XYORSKKUGAGNPC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940045998 sodium isethionate Drugs 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- KOUDKOMXLMXFKX-UHFFFAOYSA-N sodium oxido(oxo)phosphanium hydrate Chemical compound O.[Na+].[O-][PH+]=O KOUDKOMXLMXFKX-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229940083982 sodium phytate Drugs 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
- 235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 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
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000005494 tarnishing Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- JZBRFIUYUGTUGG-UHFFFAOYSA-J tetrapotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [K+].[K+].[K+].[K+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O JZBRFIUYUGTUGG-UHFFFAOYSA-J 0.000 description 1
- FODHIQQNHOPUKH-UHFFFAOYSA-N tetrapropylene-benzenesulfonic acid Chemical compound CC1CC11C2=C3S(=O)(=O)OC(C)CC3=C3C(C)CC3=C2C1C FODHIQQNHOPUKH-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- KRTNITDCKAVIFI-UHFFFAOYSA-N tridecyl benzenesulfonate Chemical compound CCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 KRTNITDCKAVIFI-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- JEVFKQIDHQGBFB-UHFFFAOYSA-K tripotassium;2-[bis(carboxylatomethyl)amino]acetate Chemical class [K+].[K+].[K+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O JEVFKQIDHQGBFB-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000004711 α-olefin Substances 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/886—Ampholytes containing P
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
Definitions
- anionic pany Cincinnati, Ohio, a corporation of Ohio nonionic, cationic, a mpholytlc, and zwitterronic deter- N Drawing Filed 4, 19 534,099 gents. Moreover, anionic brighteners remain in active Int. Cl; C07f 9/02, 9/28; C11d 1/34 form when mixed with the present reversed zwitterionic U.S. Cl. 260-924 7 Claims detergent compounds.
- the reversed zwitterionic compounds of this invention have the formula R-ZR X wherein R is an aliphatic ABSTRACT OF THE DISC RE radical, e.g., alkyl or alkenyl, containing from about 10 Reversed zwitterionic compounds having a fi fi l to about 20 carbon atoms; Z is a negatively charged radicharged center adjacent a hydrophobic chain and a posical selected from the group consisting of phosphate, phostively charged center removed by a 2 to about 4 carbon 15 Phohate, p p inate radicals; R is an alkylene radiatoms from the negatively charged center are disclosed.
- R is an aliphatic ABSTRACT OF THE DISC RE radical, e.g., alkyl or alkenyl, containing from about 10 Reversed zwitterionic compounds having a fi fi l to about 20 carbon atoms
- Z is a negatively charged radicharged center adjacent a hydrophobic chain and a
- R is an aliphatic radical, alkyl or alkenyl, Col-aim sisting of ammonium and tertiary sulfonium radicals; said ing from about 10 to about carbon atoms;
- Z is a negaammomum radical having the formula tively charged radical selected from the group consisting 20 9 of phosphate, phosphonate, and phosphinate radicals;
- NRaRaW R is an alkylene radical containing from 2 to about 4 wherein and R4 are Selected from th gr up concarbon atoms; and
- X is a positively charged radical sesisting of hydrogen, methyl, and ethyl; said tertiary sullected from the group consisting of ammonium and terfOnium radical having the formula tiary sulfonium radicals;
- the phosphate radical herein has wherein R R and R are selected from the group conthe formula sisting of hydrogen, methyl, and ethyl; said tertiary 5111- 0 fonium radical having the formula ⁇ l %Rs o wherein R and R are selected from the group consisting of methyl and ethyl.
- the reversed zwitterionic compounds The Phosphohate ladlcal herelh has the formula are useful as detergent compounds per se or can be used 0 as zwitterionic detergent components in detergent com- ⁇ l O positions.
- This invention relates to novel zwitterionic detergent compounds and to detergent compositions containing
- the Phosphmate Yadlcal herelh has the formula these compounds. These compounds have a negatively 0 charged center adjacent a hydrophobic chain, and a posill tively charged center removed by 2 to about 4 carbon (iatoms from this negatively charged center. These corn- 9 pounds are characterized herein as being reversed zwitterionic compounds to distinguish them from more conven- R R and R can be the same or different within the tional zwitterionic compounds in which a positively same molecule.
- R and R can be the same or different charged center is adjacent the hydrophobic chain, and a within the same molecule, negatively charged center is removed by two or more For purposes of organization and convenience the carbon atoms from this positively charged center.
- R R or R are hydrogen are There are several properties that are regarded as being termed zwitterionics herein. These compounds might essential for a compound to be suitable for use as a determore appropriately be classified as ampholytics since they gent. Foremost, is the cleaning ability of the comopund, deprotonate to the extent of one hydrogen over a wide i.e., its ability to remove soil, e.g., from soiled clothes.
- the detergent In pH range, including the alkaline pH range, forming the addition, the detergent should remain in active form uncorresponding compounds containing an amino moeity. der conditions of usage, e.g., at high temperatures such as Thus, in detergent compositions containing water or moisl40 F. and in aqueous solutions. Although there are a ture or under conditions of usage, these compounds are number of organic detergents which have these properties, detergent compounds such as those of the present invention which have additional desirable properties find wider scope of application.
- ampholytic form present in ampholytic form. They, however, may be isolated in zwitterionic form and are ordinarily in this form at the instant of preparation of the detergent composition containing them.
- the most preferred compounds are compounds (7) and (9) in Table I above, i.e., 2-(trimethylammonio)ethyl dodecylphosphonate and 2-(dimethylammonio)ethyl dodecylphosphonate, respectively.
- the compounds of the present invention can be prepared according to the following reaction equations wherein R, Z, R X, R R R R and R are defined as hereinbefore except as specified otherwise hereinafter.
- alkyl dichlorophosphate in Reaction V can be made by the process of Reaction I hereinbefore.
- Reactions V and VI can be carried out under the following conditions:
- R R and R are each methyl or ethyl, and none of them is hydrogen.
- the dialkylammonioalkyl alkylphosphate reactant in this equation can be made by the process of Reaction VI.
- Reaction VII can be carried out under the following conditions:
- R R and R are each methyl or ethyl, and none of them is hydrogen.
- the dialkylsirrimonioalkyl alkylphosphonate reactant in this equation can be made by the process of Reaction XVI.
- Reaction XVII can be carried out under the following conditions:
- Reaction XVIII H g 63 RIF-ON-Cl msm n on -snuz HCI
- the phosphonate reactant in the equation of Reaction XVIII can be made by the process of Reaction XIII hereinbefore.
- Reaction XVIII can be carried out under the following conditions:
- R and R are each methyl or ethyl, and neither of them is hydrogen.
- the phosphonic dihalide reactant in Reaction XV can be made by the process of Radiation XI. Reactions XV and XVI can be carried out under the following conditions:
- Tempera- Reaction Solvent ture C. Time XV Ethylene dichloride... 20-60 15 minutes, 2 hours. XVI Acetone 30-50 30 minutes, 1 hour.
- Reaction XVIII Solventethylene dichloride Temperature-50-100 C. Time-15 rnins.-2 hours Compounds wherein Z is phosphinate and X is ammonium wherein R and R are hydrogen and R is hydrogen, methyl, or ethyl:
- the reactant can be made by the process 40 of Reaction XXIV and R2 R3, and R are each methyl the 2 dimethylammoethanol addition period, the reaction or ethyl, and none of them is hydrogen.
- This reaction can mixture m the flask was malmamed at 40 50 by he carried outunder the same conditions as reaction was completed the reaction mixture in the flask was XXV.
- the phosphinic acid reactant can be made 30 by the process of Reaction XXIV; R is hydrogen and R and R are each methyl or ethyl. This reaction can be carried out under the same conditions as Reaction XXV.
- the chloroform was then evap-
- the following examples illustrate the preparation of the mated on a sfeam bath under a currept of mtrogen'
- the compounds of this invention 160-gram residue was an extremely viscous, amber paste that was hygroscopic. Thls material was equtlibrated with EXAMPLEI the atmosphere over a saturated solution of KSCN at Diisopropyl dodecylphosphonate was prepared b room temperature yielding 172 grams of clear amber gel.
- lysis of the gel showed it to be a mixture containing actlng dodecyl bromlde and trnsopropyl phosphtte ac Ana cording to the technique described in Ford-Moore and by we'ght 2(d'methy]ammm)ethy] dodecyl Phos'
- the phosphinic reactant in Reaction XXVII can be Reaction. Solvent Temperature, C. Time Williams, Journal of the Chemical Society 1947, p. 1465. Phonaie, 9- compound in Ta I hereinbefore and This reaction was carried out at a temperature of 145 10% y welght Water- C. and for a time period of 5 hours.
- EXAMPLE II Into a 2-liter, stainless-steel autoclave were added 84 grams (0.5 mole) l-dodecene, 106 grams (1.0 mole) sodium hypophosphite monohydrate, 1 ml. di-tert.-butyl peroxide, and 350 ml. methanol. The autoclave was sealed, maintained at 120 C., and rocked for 17 hours. During this 17-hour period the pressure in the autoclave was 2 atmospheres. After this 17-hour period, the contents of the autoclave were allowed to cool to room temperature, after which the autoclave was opened and the contents removed. The contents were then diluted with 3 liters of distilled water, and then extracted three times, each time with 500 ml. of petroleum ether, and the extracts discarded.
- the resulting mixture is brought to reflux, i.e., to about 101 C.
- To this refluxing mixture is added over a threehour period, grams (0.32 mole) of Z-bromoethanol. After this three-hour period, the reaction mixture is allowed to cool to room temperature, after which the precipitated sodium bromide is removed by filtration, and the toluene solvent is removed by vacuum evaporation to yield 82 grams of crude methyl-2-hydroxyethyldodecylphosphinate.
- This methyl-Z-hydroxyethyldodecylphosphinate is dissolved in 200 ml. of dry petroleum ether contained in a 500 ml. 3-necked flask, equipped with a gas dispersion tube, a drying tube, and a magnetic stirrer. Anhydrous HBr is then passed into the solution for five hours at the rate of 200 cc./min. During the HBr addition the temperature of the mixture rises and levels out at -60 C. After HBr addition, the system is swept with nitrogen for one hour to remove methyl bromide and dissolved HBr. The solvent (petroleum ether and formed water) is evaporated under nitrogen on a steam bath to yield 93 grams of crude 2-bromoethyldodecylphosphinic acid.
- Z-(dimethylethylammonio)ethyl dodecylphosphate can be prepared in the same manner as'the 2-(trimethylammonio)ethyl dodecyl hosphate above except that an equivalent amount of ethyl iodide is substituted for the methyl iodide above.
- Compounds of this invention are useful per se as detergent and surface active agents. Desirably they are used with other materials to form detergent compositions, as for example, liquid, bar, tablet, granular or other compositions.
- Such detergent compositions can contain the reversed zwitterionics of this invention, and water-soluble inorganic alkaline builder salts, water-soluble organic alkaline sequestrant builder salts or mixtures thereof in a ratio of reversed zwitterionic to builder salt of about 4:1 to about 1:20.
- Such detergent compositions ordinarily contain from 5% to of detergent active and from 5% to of builder salt.
- Granular detergent compositions preferably contain about 5% to about 50% of the reversed zwitterionics of this invention and liquid formulations preferably contain from about 2% to about 30% of such reversed zwitterionics.
- Granular detergents preferably contain at least an equal amount of an alkaline builder salt.
- Liquid formulations preferably contain from about 5% to about 40% of a water-soluble alkaline builder salt, the balance of the composition being a solvent such as water, and/or other liquid vehicles.
- Liquid formulations can also con tain a hydrotroping electrolyte, e.g., sodium toluene sulfonate. All percentages and parts herein are by weight unless specified otherwise.
- Water-soluble inorganic alkaline builder salts which can be used in this invention alone or in admixture are alkali metal carbonates, borates, phosphates, polyphos' phates, bicarbonates and silicates. Ammonium or substituted ammonium, e.g., triethanol ammonium, salts of these materials can also be used. Specific examples of suitable salts are sodium tripolyphosphate, sodium carbonate, sodium tetraborate, sodium and potassium pyrophosphate, sodium and ammonium bicarbonate, potassium tripolyphosphate, sodium hexaphosphate, sodium sesquicarbonate, sodium orthophosphate, and potassium bicarbonate.
- the preferred inorganic alkaline builders according to this invention are alkali metal tripolyphosphates for built granular and tablet compositions and alkali metal pyrophosphates for built liquid compositions.
- Potassium is the preferred alkali metal used in liquid compositions and sodium finds best application for granular or tablet compositions.
- the alkali metal salts of phytic acid, e.g., sodium phytate are also suitable as organic alkaline sequestrant builder salts (see U.S. Patent 2,739,942).
- organic alkaline sequestrant builder salts are also suitable as organic alkaline sequestrant builder salts as described in the copending application of Francis L. Diehl Ser. No. 269,359, filed Apr. 1, 1963 and now U.S. Patent 3,308,067 (e.g., polymers of itaconic acid, aconitic acid, maleic acid, mesaconic acid, fumaric acid, methylene malonic acid, and citraconic acid and copolymers with themselves and other compatible monomers such as ethylene).
- polycarboxylate polymers and copolymers as described in the copending application of Francis L. Diehl Ser. No. 269,359, filed Apr. 1, 1963 and now U.S. Patent 3,308,067 (e.g., polymers of itaconic acid, aconitic acid, maleic acid, mesaconic acid, fumaric acid, methylene malonic acid, and citraconic acid and copolymers with themselves and other compatible monomers such as
- Polyphosphonates are also valuable builders in terms of the present invention, includingspecifically sodium and potassium salts of ethane-l-hydroxy-l,l-diphosphonic acid, sodium and potassium salts of methylene diphosphonic acid, sodium and potassium salts of ethylene diphosphonic acid, and sodium and potassium salts of ethane-1,1,Z-triphosphonic acid.
- reversed zwitterionic compounds of this invention are also possible according to the present invention to use the reversed zwitterionic compounds of this invention in combination with other cleaning agents such as anionic, nonionic, and other ampholytic and zwitterionic organic detergent compounds.
- other cleaning agents such as anionic, nonionic, and other ampholytic and zwitterionic organic detergent compounds.
- anionic detergents because of the sudsing characteristics of the latter.
- the ratio of the reversed zwitterionic to such other detergent compound is from about 10:1 to 1:5.
- the ratio of such a mixture to the builder salt should be within the previously prescribed range of 4:1 to 1:20.
- a composition prepared along these lines can contain from 5% to 50% of such a mixture and 5% to 85% of a builder salt selected from water-soluble inorganic alkaline builder salts, water-soluble organic sequestrant builder salts, and mixtures thereof, within the prescribed ratio range.
- anionic soap detergents which can be used in admixture with the reversed zwitterionic detergent, if desired, are the sodium, potassium, ammonium and alkylolammonium salts of higher detergent range 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 organic nonsoap detergents in the form of their water-soluble salts are: alkylglycerylethersulfonates; alkyl sulfates; alkyl monoglyceride sulfates or sulfonates; alkylpolyethenoxy ether sulfates; acylsarcosinates; acyl esters of isethionates;
- N-acyl-N-methyl taurides N-acyl-N-methyl taurides; alkylbenzenesulfonates wherein the alkyl substituent is straight chain or branched chain; sulfonated alpha-olefins, e.g., such as described in the copending application of Kessler et al., Ser. No. 561,397, filed June 29, 1966 and now US. Patent 3,332,880; alkylphenol polyethenoxy sulfonates.
- the alkyl and acyl groups respectively, contain 10 to 24 carbon atoms. They are used in the form of water-soluble salts, the sodium, potassium, ammonium, and alkylolammonium salts, for example.
- sodium la-uryl sult'ate sodium tallow alkyl sulfate
- sodium salt of sulfonated alpha-tridecene potassium N-methyl-N- lauroyl tauride
- triethanolammonium tetrapropylbenzene sulfonate sodium (linear) dodecyl benzene sulfonate.
- nonionic organic detergents which can be used in the compositions of this invention, if desired, are: polyethylene oxide condensates of alkylphenols wherein the alkyl group contains from 8 to 15 carbon atoms (e.g., t-octylphenol) and the ethylene oxide is present in a molar ratio of ethylene oxide to alkylphenol in the range of 8:1 to 20:1; condensation products of ethylene oxide with the product resulting from the reacti n of propylene oxide and ethylene diamine wherein the molecular weight of the condensation products ranges from 5000 to 11,000; the condensation products of from about to 30 moles of ethylene oxide with one mole of a straight or branched chain aliphatic alcohol containing from 8 to 18 carbon atoms, e.g., condensation product of 6 moles of ethylene oxide with one mole of lauryl alcohol; higher alkyl di-lower alkyl amine or phosphi1e oxides, e.g., dodecyl
- Ampholytic synthetic detergents 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 substituents contains from about to about 20 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, phosphinate, or phosphonate, Examples of compounds falling within this definition are sodium 3-dodecylaminopropiqnate, sodium 3-(N-methyl-N-hexadecylamino)-2-hydroxypropane-l-sulfonate and its dodecyl homolog, sodium 3-dodecylaminopropane-l-sulfonate, sodium dodecyl-beta-alanine, sodium N-alkyltaurines such as the one prepared by reacting dodecylamine with sodium isethionate
- N-higher alkyl aspartic acids such as those produced according to the teaching of United States Letters Patent No. 2,438,091, and the products sold under the trade name Miranol and described in United States Letters Patent No. 2,528,378.
- Zwitterionic synthetic detergents can be broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radical may be straight chain or branched, and wherein one of the aliphatic substituents contains from about 10 to about 20 carbon atoms and one contains an anionic water solubilization group, e.g., carboxy, sulfonate, sulfate, phosphate, phosphinate, or phosphonate.
- an anionic water solubilization group e.g., carboxy, sulfonate, sulfate, phosphate, phosphinate, or phosphonate.
- Examples of compounds falling within this definition are: 3 (N,N-dimethyl-N-hexadecylammonio)-2-hydroxypropane-l-sulfonate and the corresponding dodecyl and tetradecyl homologs and 3 (N,N-dimethyl-N-dodecylammonio)-propane-1-sulfonate and the corresponding hexadecyl and tetradecyl homologs.
- a detergent composition employing the combination of ingredients ordinarily can contain from about 0.01% by weight to about 2% by weight optical brightener.
- anionic optical brighteners which can be used herein are sodium 2-sulfo- 4-(2-naptho-1,2-triazolyl)stilbene and sodium 4,4-bis(4- anilino-6-morpholino s triazo-Z-ylamino)-2,2'-stilbene disulfonate.
- the detergent compositions of this invention can also contain any of the usual adjuvants, diluents, and additives, for example, perfumes, anti-tarnishing agents, bacteriostatic agents, dyes, suds builders, suds depressors, and the like, without detracting from the advantageous properties of the composition.
- EXAMPLE IX Liquid Percent 2-(dimethylsulfonio)ethyl decylphosphonate 5.0 Sodium salt of S0 sulfonated 1:1 weight mixture of alpha-dodecene and alpha-tetradecene 10.0 Tetrapotassium pyrophosphate 19.0 Sodium silicate (NflzOZSiOg 1I1-6) 3.8 Potassium toluene sulfonate 8.5 Carboxymethyl hydroxyethyl cellulose .3 Water Balance 15 EXAMPLE X Liquid Percent 2-(dicthylsulfonio)ethyl decylphosphate 6.0 Sodium (linear) dodecyl benzene sulfonate 6.0
- reversed zwitterionic compounds used in the present invention can be incorporated into many other liquid or granular detergent compositions with suitable adjustments being made in the other components.
- tarnish inhibitor such as benzotriazole or ethylene thiourea may be added in amounts up to about 1%.
- opacifiers and blending or viscosity control agen'sywhi le not essential in the compositions of this invention, mi ⁇ ! also be added.
- compositions of the present invention can be used in conjunction with cool water washing situations as well as with warm and hot water.
- a reversed zwitterionic detergent compound havin the formula R--Z-R --X wherein R is seected from alkyl and alkenyl of from about 10 to about 20 carbon atoms; Z is a negatively charged radical selected from the group consisting of phosphate, phosphonate, and phosphinate radicals; R is an alkylene radical containing from 2 to about 4 carbon atoms; and X is a positively charged radical selected from the group consisting of ammoniuin and tertiary sulfonium radicals; said ammonium radical having the formula wherein R R and R are each selected from the group consisting of hydrogen, methyl, and ethyl; said tertiary sulfonium radical having the formula as s RSRO wherein R and R are each selected from the group consisting of methyl and ethyl.
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Description
25 2 9 5 caoss REFERENCE 5 mruggg United States Patent 3,507,937 Patented Apr. 21, 1970 "ice 3 507 937 The novel reversed zwitterionic compounds f hi i vention clean as well as tetrapropylenebenzene sulfonate. REVERSED PHOSPHORUS They remain in active form during conditions ordinarily Roger E. Zimmerer, Springfield Township, Hamilton encountered during washing. In addition, they remain in County, Ohio, assignor to The Procter & Gamble Com- 5 actiYe l mixed with. builders i i anionic pany, Cincinnati, Ohio, a corporation of Ohio nonionic, cationic, a mpholytlc, and zwitterronic deter- N Drawing Filed 4, 19 534,099 gents. Moreover, anionic brighteners remain in active Int. Cl; C07f 9/02, 9/28; C11d 1/34 form when mixed with the present reversed zwitterionic U.S. Cl. 260-924 7 Claims detergent compounds.
The reversed zwitterionic compounds of this invention have the formula R-ZR X wherein R is an aliphatic ABSTRACT OF THE DISC RE radical, e.g., alkyl or alkenyl, containing from about 10 Reversed zwitterionic compounds having a fi fi l to about 20 carbon atoms; Z is a negatively charged radicharged center adjacent a hydrophobic chain and a posical selected from the group consisting of phosphate, phostively charged center removed by a 2 to about 4 carbon 15 Phohate, p p inate radicals; R is an alkylene radiatoms from the negatively charged center are disclosed. cal cohtammg from 2 tQabOl-It 4 carbon atoms; and X is These compounds have the formula 1 wherea positively charged radical selected from the group conin R is an aliphatic radical, alkyl or alkenyl, Col-aim sisting of ammonium and tertiary sulfonium radicals; said ing from about 10 to about carbon atoms; Z is a negaammomum radical having the formula tively charged radical selected from the group consisting 20 9 of phosphate, phosphonate, and phosphinate radicals; NRaRaW R is an alkylene radical containing from 2 to about 4 wherein and R4 are Selected from th gr up concarbon atoms; and X is a positively charged radical sesisting of hydrogen, methyl, and ethyl; said tertiary sullected from the group consisting of ammonium and terfOnium radical having the formula tiary sulfonium radicals; said ammonium radical having e the formula wherein R and R are selected from the group consisting NR R R of methyl and ethyl. The phosphate radical herein has wherein R R and R are selected from the group conthe formula sisting of hydrogen, methyl, and ethyl; said tertiary 5111- 0 fonium radical having the formula {l %Rs o wherein R and R are selected from the group consisting of methyl and ethyl. The reversed zwitterionic compounds The Phosphohate ladlcal herelh has the formula are useful as detergent compounds per se or can be used 0 as zwitterionic detergent components in detergent com- {l O positions.
This invention relates to novel zwitterionic detergent compounds and to detergent compositions containing The Phosphmate Yadlcal herelh has the formula these compounds. These compounds have a negatively 0 charged center adjacent a hydrophobic chain, and a posill tively charged center removed by 2 to about 4 carbon (iatoms from this negatively charged center. These corn- 9 pounds are characterized herein as being reversed zwitterionic compounds to distinguish them from more conven- R R and R can be the same or different within the tional zwitterionic compounds in which a positively same molecule. R and R can be the same or different charged center is adjacent the hydrophobic chain, and a within the same molecule, negatively charged center is removed by two or more For purposes of organization and convenience the carbon atoms from this positively charged center. above compounds wherein R R or R are hydrogen are There are several properties that are regarded as being termed zwitterionics herein. These compounds might essential for a compound to be suitable for use as a determore appropriately be classified as ampholytics since they gent. Foremost, is the cleaning ability of the comopund, deprotonate to the extent of one hydrogen over a wide i.e., its ability to remove soil, e.g., from soiled clothes. In pH range, including the alkaline pH range, forming the addition, the detergent should remain in active form uncorresponding compounds containing an amino moeity. der conditions of usage, e.g., at high temperatures such as Thus, in detergent compositions containing water or moisl40 F. and in aqueous solutions. Although there are a ture or under conditions of usage, these compounds are number of organic detergents which have these properties, detergent compounds such as those of the present invention which have additional desirable properties find wider scope of application.
present in ampholytic form. They, however, may be isolated in zwitterionic form and are ordinarily in this form at the instant of preparation of the detergent composition containing them.
3 Reversed zwitterionic detergent compounds, none of which are known to be described in the prior art, and exemplary of those within the scope of the present invention are set forth in Table I below wherein R, Z, R Z, R R R R and R are applied in the formulas set forth above.
ROl -OR NR R NaOH noi ow innmi NaCl In these equations R and R are each methyl or ethyl,
TABLE I R Z R X B R R R R (l) deeyl phosphate ethylene ammonium methyl methyl methyl dodecyl phosphate ethylene ammonium methyl methyl methyl tetradecyl phosphate trimethylene ammonium methyl methyl methyl octadecyl phosphate tetramethylene ammonium hydrogen methyl methyl octadecyl phosphate ethylene tertiary sulonium ethyl ethyl deeyl phosphonate tetramethylene tertiary sultonium methyl ethyl dodecyl phosphonate ethylene ammonium methyl methyl methyl (8 dodecyl phosphonate trimethylene ammonium ethyl ethyl ethyl (9) dodecyl phosphonate thylene ammonium hydrogen methyl methyl idecyl phosphonate ethylene ammonium hydrogen methyl ethyl hexadecyl phosphonate tetramethylene tertiary sull'onium methyl methyl oleyl phosphonate ethylene ammonium methyl ethyl ethyl eicosyl phosphonate ethylene ammonium hydrogen hydrogen hydrogen deeyl phosphinate tetramethylene ammonium hydrogen hydrogen methyl dodecyl phosphinate ethylene ammonium methyl methyl methyl dodecyl phosphinate ethylene tertiary sullonium methyl methyl hexadecyl phosphinate trimethylene ammonium methyl methyl methyl octadeeyl phosphinate ethylene ammonium hydrogen ethyl ethyl octadecyl phosphinate ethylene ammonium hydrogen methyl ethyl eicosyl phosphinate ethylene ammonium hydrogen hydrogen ethyl (2l) dodecyl phosphate ethylene ammonium hydrogen methyl methyl Preferred reversed zwitterionics of this invention are those compounds wherein R defined generally above contains from 12 to 16 carbon atoms, and X defined generally above is a quaternary ammonium radical or an ammonium radical containing only one hydrogen. The most preferred compounds are compounds (7) and (9) in Table I above, i.e., 2-(trimethylammonio)ethyl dodecylphosphonate and 2-(dimethylammonio)ethyl dodecylphosphonate, respectively.
The compounds of the present invention can be prepared according to the following reaction equations wherein R, Z, R X, R R R R and R are defined as hereinbefore except as specified otherwise hereinafter.
Compounds wherein Z is phosphate and X is ammonium wherein R and R are hydrogen and R is hydrogen, methyl, or ethyl:
hydrogen, methyl, or ethyl. These reactions can be carried out under the following conditions:
Temperature, C.
Reaction Solvent Time 2 hours, 4 hours.
Compounds wherein Z is phosphate and X is ammonium, wherein R is hydrogen and R and R are methyl or ethyl:
and neither of them is hydrogen. The alkyl dichlorophosphate in Reaction V can be made by the process of Reaction I hereinbefore. Reactions V and VI can be carried out under the following conditions:
Tempera- Reaetion Solvent ature, C. Time V Ethylene diehloride VI Methanol 25-40 2 hours, 4 hours. 25-30 15 minutes, 45 minutes.
Compounds wherein Z is phosphate and X is quaternary ammonium:
ll 69 ROZ-OR NRHUR NaI H20 In this equation R R and R are each methyl or ethyl, and none of them is hydrogen. The dialkylammonioalkyl alkylphosphate reactant in this equation can be made by the process of Reaction VI. Reaction VII can be carried out under the following conditions:
I Reaction VII Solvent-dioxane Temperature--refiux (about C. for dioxane) Time-15 mins.45 mins.
Compounds wherein Z is phosphate and X is tertiary sulfonium:
So1ventethylene dichloride Temperature-5O C.--l 00 C. Time-15 mins.-2 hours Compounds wherein Z is phosphonate and X is ammonium wherein R and R are hyd;ogen and R is hydrogen, methyl, or ethyl:
OH XIV.
i u RPOR CI NR2R3R4 RIIJORINRZRKRI IICl ea H 0 These reactions can be carried out under the following conditions:
Compounds wherein Z is phosphonate and X is quaternary ammonium:
XVII.
In this equation R R and R are each methyl or ethyl, and none of them is hydrogen. The dialkylsirrimonioalkyl alkylphosphonate reactant in this equation can be made by the process of Reaction XVI. Reaction XVII can be carried out under the following conditions:
Reaction-XVII Solventethyl alcohol Temperature- C.-80 C. Tirrie-3-6 hours Compounds wherein Z is phosphonate and X is tertiary sulfonium:
x VIII.
H g 63 RIF-ON-Cl msm n on -snuz HCI The phosphonate reactant in the equation of Reaction XVIII can be made by the process of Reaction XIII hereinbefore. Reaction XVIII can be carried out under the following conditions:
Tempera- Solvent ture, C.
Time
Reaction:
IX Excess trialkylphosphrte. 140-150 4 hours, 8 hours. 15 minutes, 1 hour. 1 hour, 2 hours.
2 hours, 4 hours.
30 minutes, 1 hour. 1 hour, 3 hours.
Compounds wherein Z is phosphonate and X is ammonium wherein R is hydrogen and R and R are methyl or ethyl:
l 63 RiOR NHR R NaCl HzCO;
In these equations R and R are each methyl or ethyl, and neither of them is hydrogen. The phosphonic dihalide reactant in Reaction XV can be made by the process of Radiation XI. Reactions XV and XVI can be carried out under the following conditions:
Tempera- Reaction Solvent ture, C. Time XV Ethylene dichloride... 20-60 15 minutes, 2 hours. XVI Acetone 30-50 30 minutes, 1 hour.
Reaction XVIII Solventethylene dichloride Temperature-50-100 C. Time-15 rnins.-2 hours Compounds wherein Z is phosphinate and X is ammonium wherein R and R are hydrogen and R is hydrogen, methyl, or ethyl:
XIX. 0
ll di-terL-butyl perotide R CH=CHz HP-OHs RP-ONa 2atmospheres RIlONa HCl RIF-0H NaCl H H XXI.
XXV. copending application of Roy, Ser. No. 218,863 filed Aug.
23, 1962 and now abandoned.
196 grams (0.78 mole) dodecylphosphonic acid was e placed in a 1-liter flask. This flask was then placed on a steam bath. To this flask on the steam bath was added In equation XIX, R is an aliphatic radical containing two over a 15-minute period 360 grams (1.7 moles) PCl less carbon atoms than the desired R. In equation XXV, This addition was carried out under dry nitrogen. The R and R are each hydrogen, and R is hydrogen, methyl formed mixture was maintained on the steam bath for or ethyl. Reactions XIX-XXV can be carried out under one hour after the PCl addition was completed. During the following conditions: the PCl addition and thereafter the temperature of the Reaction Solvent Temperatures, C. Time XIX Methanol ncmao -20 hours. XX Water/diethy1ether -35..." 5 minutes.
Diethyl ether- 0-10 10-30 minutes.
Toluene 3-5 hours XXV Acetone Reflux (about 56 C. for acetone). 5-10 hours.
Compounds whereZis phosphinate andXis ammonium mixture was maintained at 90-100 C. by the steam wherein R is hydrogen and R and R are methyl Or bath. The flask was then removed from the steam ethyl: bath. The excess PCl in the reaction mixture was then XXVL converted to POCl by rapidly passing S0 into the re- 0 O action mixture for 90 minutes. The POCl and SoCl in g q; the mixture were then removed from the mixture under 3 R I vacuum, and the residue was distilled to yield 210 grams R Br 0 (0.73 mole) of substantially pure dodecylphosphonic dichloride, having a boiling point ranging from 117 C. to 119 C. at 0.1 mm. Hg. 1
400 ml. of triethylamine having been dried over CaSO was then introduced into a 1-liter, 3-necked, roundbottom flask, equipped with a thermometer, a condenser protected with a drying tube, an addition funnel, and a mechanical stirrer. Then, 143.5 grams (0.5 mole) of f Y dodecylphosphonic dichloride was added to the flask with RP-OH 2NR R R RP-IUNRIUR HBr-NWRR stirring over a 45-minute period. Next, 44.5 grams (0.5
mm 6 mole) of Z-dimethylaminoethanol was added to the flask dropwise with stirring over a -minute period. During In this equation, the reactant can be made by the process 40 of Reaction XXIV and R2 R3, and R are each methyl the 2 dimethylammoethanol addition period, the reaction or ethyl, and none of them is hydrogen. This reaction can mixture m the flask was malmamed at 40 50 by he carried outunder the same conditions as reaction was completed the reaction mixture in the flask was XXV.
stirred for one additional hour at C. The reaction Compounds wherem Z 15 phosphmate and x temary mixture was then allowed to cool to room temperature.
In this equation, the phosphinic acid reactant can be made 30 by the process of Reaction XXIV; R is hydrogen and R and R are each methyl or ethyl. This reaction can be carried out under the same conditions as Reaction XXV.
Compounds ,wherein Z is phosphinate and X is quaternary ammonium: 35
sulfomum: 40 To this reaction mixture at room temperature was XXVIII- added dropwise, with stirring, over a 30-minute period, 20
ml. (1.1 mole) of water. During the water addition, the
Q mask temperature of the reaction mixture rose rapidly, and
- 1 b was maintained at about 60 C. by means of a cold water R SR bath. After the 30-minute water addition period, 180 ml.
XXIX- 3 i of water was poured into the reaction mixture to eflect Ri'oNa R 1 RP-R SIUR NaI complete solution of the reaction mixture.
318R 9 To this solution was added 1 liter of water containing grams (1.5 moles) of sodium hydroxide. This addition was carried out by pouring the sodium hydroxide solution mafje by the pr cess of Reaction XXV heiehnbefore fi into the reaction solution. The temperature of the formed muons XV i X can be came out er solution was about 35 C. during and after sodium hythe following commons droxide addition. The formed solution was evaporated 60 on a steam bath under a current of nitrogen. The residue resulting from this evaporation was digested in 1 liter of 583313--. D m u 3 ifig fi g boiling chloroform, and the insoluble materials were then removed by filtration. The chloroform was then evap- The following examples illustrate the preparation of the mated on a sfeam bath under a currept of mtrogen' The compounds of this invention: 160-gram residue was an extremely viscous, amber paste that was hygroscopic. Thls material was equtlibrated with EXAMPLEI the atmosphere over a saturated solution of KSCN at Diisopropyl dodecylphosphonate was prepared b room temperature yielding 172 grams of clear amber gel.
lysis of the gel showed it to be a mixture containing actlng dodecyl bromlde and trnsopropyl phosphtte ac Ana cording to the technique described in Ford-Moore and by we'ght 2(d'methy]ammm)ethy] dodecyl Phos' The phosphinic reactant in Reaction XXVII can be Reaction. Solvent Temperature, C. Time Williams, Journal of the Chemical Society 1947, p. 1465. Phonaie, 9- compound in Ta I hereinbefore and This reaction was carried out at a temperature of 145 10% y welght Water- C. and for a time period of 5 hours. The formed diiso- Into a 3- d, r nd-bottom flask, equipped propyl dodecylphosphonate is converted to dodecylphoswith a heating mantle, a reflux condenser, and a mechanphonic acid using the pyrolytic method described in the 75 ical stirrer, was charged grams of the above gel [0.34
'cooling. After addition of the 2-dimethylaminoethanolmole 2- (dimethylammonio)ethyl dodecylphosphonate] dissolved in 500 ml. of denatured ethyl alcohol. To this solution was added 52.5 grams (0.37 mole) of methyl iodide. This addition was carried out over a 10-minute period. During this addition, the formed mixture was maintained at a temperature of 60-70 C. After this addition, the mixture was borught to reflux temperature, i.e., about 78 C., and was stirred at reflux temperature for four hours. At this point, the reflux condenser was replaced with a distillation head and condenser, and 350 ml. of alcohol was removed by distillation. To the resulting mixture was added with stirring 340 ml. of l N NaOH (0.34 mole NaOI-I). This addition was carried out all at once. During this addition the temperature of the mixture was maintained at 70-80 C. The solvent in the mixture was then evaporated on a steam bath. To the residue was added 1000 ml. water to form a reaction solution. This solution was mixed with about 0.5 equivalent of cation exchange resin in the hydrogen form and with about 0.5 equivalent of anion exchange resin in the hydroxide form. After about 30 minutes during which the mixture was periodically shaken, the resin was removed by filtration. The water in the filtrate was evaporated on a steam bath to provide an amber solid which was equilibrated over saturated KSCN solution at room temperature to yield 101 grams of clear, amber gel. Analysis of this gel showed it to be a mixture of 84% by weight Z-(trimethylammonio)-ethyl dodecylphosphonate, i.e., compound (7) in Table I hereinbefore, 1l% by weight Water, and by weight sodium iodide.
2 (dimethylethylammonio)ethyl dodecylphosphonate can be prepared as above except that an equivalent amount of ethyl iodide is substituted for the methyl iodide above.
EXAMPLE II Into a 2-liter, stainless-steel autoclave were added 84 grams (0.5 mole) l-dodecene, 106 grams (1.0 mole) sodium hypophosphite monohydrate, 1 ml. di-tert.-butyl peroxide, and 350 ml. methanol. The autoclave was sealed, maintained at 120 C., and rocked for 17 hours. During this 17-hour period the pressure in the autoclave was 2 atmospheres. After this 17-hour period, the contents of the autoclave were allowed to cool to room temperature, after which the autoclave was opened and the contents removed. The contents were then diluted with 3 liters of distilled water, and then extracted three times, each time with 500 ml. of petroleum ether, and the extracts discarded.
Into the aqueous solution remaining was poured 100 ml. of concentrated hydrochloric acid. During this addition the temperature of the resulting mixture was approximately 35 C. The resulting mixture was extracted three times, each time with 500 ml. of petroleum ether, and the remaining aqueous phase was discarded. These ether extracts were dried over sodium sulfate, and the dried extracts were evaporated on a steam bath under nitrogen to yield 98 grams of crude dodecylphosphinic acid. Recrystallization from 300 ml. of petroleum ether gave 79 grams (0.34 mole) of substantially pure dodecylphosphinic acid.
70 grams (0.3 mole) of this substantially pure dodecylphosphinic acid is then dissolved in 200 ml. diethyl ether at 0 C. To this solution is added a diethyl ether solution of diazomethane prepared by adding 30 grams of N-nitrosomethylurea to a mixture of 75 ml. of 30% aqueous KOH and 250 ml. diethyl ether at 010 C., and decanting the ether layer from the aqueous layer prior to use. The diazomethane and dodecylphosphinic acid are reacted for 30 minutes at 0-10 C. The produced methyl dodecylphosphinate, 74 grams, is isolated by evaporating the diethyl ether and excess diazomethane on a steam bath under nitrogen.
72 grams (0.28 mole) of this methyl dodecylphosphinate is then dissolved in 250 ml. of toluenewhich has been dried over sodium ribbon. This solution is mixed with 6.5 grams (0.28 mole) sodium dispersed in 250 ml. toluene in a 1-liter, 3-necked, round-bottom flask, equipped with addition funnel, thermometer, reflux condenser protected by a drying tube, and mechanical stirrer. The sodio derivative of the phosphinate is formed by stirring the mixture at 25 C.- C. for four hours.
The resulting mixture is brought to reflux, i.e., to about 101 C. To this refluxing mixture is added over a threehour period, grams (0.32 mole) of Z-bromoethanol. After this three-hour period, the reaction mixture is allowed to cool to room temperature, after which the precipitated sodium bromide is removed by filtration, and the toluene solvent is removed by vacuum evaporation to yield 82 grams of crude methyl-2-hydroxyethyldodecylphosphinate.
This methyl-Z-hydroxyethyldodecylphosphinate is dissolved in 200 ml. of dry petroleum ether contained in a 500 ml. 3-necked flask, equipped with a gas dispersion tube, a drying tube, and a magnetic stirrer. Anhydrous HBr is then passed into the solution for five hours at the rate of 200 cc./min. During the HBr addition the temperature of the mixture rises and levels out at -60 C. After HBr addition, the system is swept with nitrogen for one hour to remove methyl bromide and dissolved HBr. The solvent (petroleum ether and formed water) is evaporated under nitrogen on a steam bath to yield 93 grams of crude 2-bromoethyldodecylphosphinic acid.
This crude 2-bromoethyldodecylphosphinic acid is dis solved in 200 ml. acetone. Into this solution is poured grams (1 mole) of trimethylamine. This mixture contained in a 500 ml. boiling flask surmounted with a reflux condenser is refluxed at about 56 C. for 8 hours. The resulting mixture is evaporated on a steam bath. The residue is dissolved in 200 ml. of methanol. This solution is shaken for 30 minutes with a mixture of 0.5 equivalent of cation exchange resin in the hydrogen form and 0.5 equivalent of anion exchange resin in the hydrox ide form. The resins are then removed by filtration. The filtrate is evaporated to yield grams of 2-(trimethylammonio)ethyl dodecylphosphinate, i.e., compound (15) in Table I hereinbefore.
2 (dimethylethylammonio)ethyl dodecylphosphinate and 2-(triethylammonio)ethyl dodecylphosphinate can be prepared as above except that dimethylethylamine and triethylamine, respectively, are substituted for the trimethylamine above.
In another case, grams (0.3 mole) of 2-bromoethyldodecylphosphinic acid prepared as above is dissolved in 500 ml. of dioxane. To this solution is added 45 grams (0.64 mole) sodium methyl mercaptide. This mixture is maintained at 30 C. for 18 hours. A fast stream of nitrogen is passed through the mixture to remove methyl mercaptan. To the resulting mixture is added 50 grams (0.45 mole) methyl iodide. This reaction mixture is re fluxed at about 101 C. for 4 hours. Purification of the refluxed mixture yields 88 grams of 2- (dimethylsulfonio) ethyl dodecylphosphinate, i.e., compound (16) in Table I hereinbefore.
- EXAMPLE III Into a l-liter, 3-necked flask, equipped with a thermometer, gas inlet tube, dropping funnel, and mechanical stirring assembly is placed 106 grams (0.69 mole) of POCl and 500 ml. of dry ethylenedichloride. To this formed solution, with stirring, is added dropwise over a 30-minute period 93 grams (0.5 mole) of l-dodecanol. During this addition, dry nitrogen is passed slowly through the stirred solution. The temperature of the solution starts out at room temperature, i.e., 25 C., and rises about 5 C. during the dodecanol addition. Stirring is continued for 3 hours after addition is completed, during which the temperature of the reaction solution ranges from 25 C. to 30 C. The excess POCl and the ethylenedichloride are then removed by evaporation under 11 water pump vacuum using a 70 C. water bath to speed the evaporation.
The residue from the evaporation, consisting of crude dodecyl dichlorophosphate, is dissolved in 500 ml. of dry ethylenedichloride in apparatus identical with that described in the above paragraph. To this solution is added with stirring over a 45-minute period, 44 grams (0.5 mole) 2-(dimethylamino)ethanol. Stirring is continued for 2 hours after this addition. During the Z-(dimethylamino)ethanol addition period and during the stirring thereafter the temperature of the reaction solution ranges from C. to C. The solvent is then removed by vacuum evaporation.
The residue from this evaporation is dissolved in 500 ml. of methanol containing grams of NaOH and 50 ml. water. This solution is shaken from time to time during a thirty-minute period 'with a mixture of 1.5 equivalents of cation exchange resin in the hydrogen form and 1.5 equivalents of anion exchange resin in the hydroxide form. The resin is then removed by filtration. The solvent is then evaporated to yield 147 grams of 2-(dimethylammonio)ethyl dodecylphosphate, i.e., compound (21) in Table I above.
In another case, 100 grams (0.3 mole) of 2-dimethy1- ammonio)ethyl dodecylphosphate prepared as above is dissolved in 500 ml. dioxane. To this solution is added over a 10-minute period, grams (0.32 mole) of methyl iodide. The mixture is then brought to reflux temperature, i.e., to about 105 C., and is stirred at this temperature for 30 minutes. To the resulting mixture is added with stirring over a 5-minute period 300 ml. of l N NaOH (0.3 mole NaOH). The temperature of the mixture during this addition ranges from 100 C. to 72 C. The resulting mixture is purified by ion exchange to yield 94 grams of Z-(trimethylammonio)-ethyl dodecylphosphate, i.e., compound (2) in Table I hereinbefore.
Z-(dimethylethylammonio)ethyl dodecylphosphate can be prepared in the same manner as'the 2-(trimethylammonio)ethyl dodecyl hosphate above except that an equivalent amount of ethyl iodide is substituted for the methyl iodide above.
Compounds of this invention are useful per se as detergent and surface active agents. Desirably they are used with other materials to form detergent compositions, as for example, liquid, bar, tablet, granular or other compositions. Such detergent compositions can contain the reversed zwitterionics of this invention, and water-soluble inorganic alkaline builder salts, water-soluble organic alkaline sequestrant builder salts or mixtures thereof in a ratio of reversed zwitterionic to builder salt of about 4:1 to about 1:20. Such detergent compositions ordinarily contain from 5% to of detergent active and from 5% to of builder salt.
Granular detergent compositions preferably contain about 5% to about 50% of the reversed zwitterionics of this invention and liquid formulations preferably contain from about 2% to about 30% of such reversed zwitterionics. Granular detergents preferably contain at least an equal amount of an alkaline builder salt. Liquid formulations preferably contain from about 5% to about 40% of a water-soluble alkaline builder salt, the balance of the composition being a solvent such as water, and/or other liquid vehicles. Liquid formulations can also con tain a hydrotroping electrolyte, e.g., sodium toluene sulfonate. All percentages and parts herein are by weight unless specified otherwise.
Water-soluble inorganic alkaline builder salts which can be used in this invention alone or in admixture are alkali metal carbonates, borates, phosphates, polyphos' phates, bicarbonates and silicates. Ammonium or substituted ammonium, e.g., triethanol ammonium, salts of these materials can also be used. Specific examples of suitable salts are sodium tripolyphosphate, sodium carbonate, sodium tetraborate, sodium and potassium pyrophosphate, sodium and ammonium bicarbonate, potassium tripolyphosphate, sodium hexaphosphate, sodium sesquicarbonate, sodium orthophosphate, and potassium bicarbonate. The preferred inorganic alkaline builders according to this invention are alkali metal tripolyphosphates for built granular and tablet compositions and alkali metal pyrophosphates for built liquid compositions. Potassium is the preferred alkali metal used in liquid compositions and sodium finds best application for granular or tablet compositions.
Examples of suitable organic alkaline sequestrant builder salts used in this invention alone or in admixture are alkali metal, ammonium or substituted ammonium, aminocarboxylates, e.g., sodium and potassium ethylenediaminetetraacetate, sodium and potassium N-(Z-hydroxyethyl)-nitrilodiacetates, sodium and potassium nitrilotriacetates. Mixed salts of these polycarboxylates are also suitable. The alkali metal salts of phytic acid, e.g., sodium phytate are also suitable as organic alkaline sequestrant builder salts (see U.S. Patent 2,739,942). Also suitable as organic alkaline sequestrant builder salts are the watersoluble salts of polycarboxylate polymers and copolymers as described in the copending application of Francis L. Diehl Ser. No. 269,359, filed Apr. 1, 1963 and now U.S. Patent 3,308,067 (e.g., polymers of itaconic acid, aconitic acid, maleic acid, mesaconic acid, fumaric acid, methylene malonic acid, and citraconic acid and copolymers with themselves and other compatible monomers such as ethylene).
Polyphosphonates are also valuable builders in terms of the present invention, includingspecifically sodium and potassium salts of ethane-l-hydroxy-l,l-diphosphonic acid, sodium and potassium salts of methylene diphosphonic acid, sodium and potassium salts of ethylene diphosphonic acid, and sodium and potassium salts of ethane-1,1,Z-triphosphonic acid. Other examples include the alkali metal salts of ethane-Z-carboxy-l,l-diphosphonic acid, hydroxymethanediphosphonic acid, carbonyldiphosphonic acid, ethane-l-hydroxy-1,1,2-triphosphonic acid, ethane-2-hydroxy-1,1,Z-triphosphonic acid, propanel,1,3,3-tetraphosphonic acid, propanel 1 ,2,3-tetraphosphonic acid, and propane-1,2,2,3-tetraphosphonic acid.
Besides the builders being used together with the present reversed zwitterionics, it is also possible according to the present invention to use the reversed zwitterionic compounds of this invention in combination with other cleaning agents such as anionic, nonionic, and other ampholytic and zwitterionic organic detergent compounds. When it is desired to use such reversed zwitterionic compounds in combination with other detergent compounds, they are preferably utilized with anionic detergents because of the sudsing characteristics of the latter. The ratio of the reversed zwitterionic to such other detergent compound is from about 10:1 to 1:5. If it is desired to use such a reversed zwitterionic in admixture with another detergent compound as the active portion of a cleaning composition, the ratio of such a mixture to the builder salt should be within the previously prescribed range of 4:1 to 1:20. A composition prepared along these lines can contain from 5% to 50% of such a mixture and 5% to 85% of a builder salt selected from water-soluble inorganic alkaline builder salts, water-soluble organic sequestrant builder salts, and mixtures thereof, within the prescribed ratio range.
Examples of anionic soap detergents which can be used in admixture with the reversed zwitterionic detergent, if desired, are the sodium, potassium, ammonium and alkylolammonium salts of higher detergent range 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. Examples of suitable anionic organic nonsoap detergents in the form of their water-soluble salts are: alkylglycerylethersulfonates; alkyl sulfates; alkyl monoglyceride sulfates or sulfonates; alkylpolyethenoxy ether sulfates; acylsarcosinates; acyl esters of isethionates;
N-acyl-N-methyl taurides; alkylbenzenesulfonates wherein the alkyl substituent is straight chain or branched chain; sulfonated alpha-olefins, e.g., such as described in the copending application of Kessler et al., Ser. No. 561,397, filed June 29, 1966 and now US. Patent 3,332,880; alkylphenol polyethenoxy sulfonates. In these compounds the alkyl and acyl groups, respectively, contain 10 to 24 carbon atoms. They are used in the form of water-soluble salts, the sodium, potassium, ammonium, and alkylolammonium salts, for example. Specific examples are: sodium la-uryl sult'ate, sodium tallow alkyl sulfate; sodium salt of sulfonated alpha-tridecene; potassium N-methyl-N- lauroyl tauride; triethanolammonium tetrapropylbenzene sulfonate; sodium (linear) dodecyl benzene sulfonate.
Examples of nonionic organic detergents which can be used in the compositions of this invention, if desired, are: polyethylene oxide condensates of alkylphenols wherein the alkyl group contains from 8 to 15 carbon atoms (e.g., t-octylphenol) and the ethylene oxide is present in a molar ratio of ethylene oxide to alkylphenol in the range of 8:1 to 20:1; condensation products of ethylene oxide with the product resulting from the reacti n of propylene oxide and ethylene diamine wherein the molecular weight of the condensation products ranges from 5000 to 11,000; the condensation products of from about to 30 moles of ethylene oxide with one mole of a straight or branched chain aliphatic alcohol containing from 8 to 18 carbon atoms, e.g., condensation product of 6 moles of ethylene oxide with one mole of lauryl alcohol; higher alkyl di-lower alkyl amine or phosphi1e oxides, e.g., dodecyldimethylamine oxide or dodeclyd methyl phosphine oxide; alkyl methyl sulfoxides such as dodecyl methyl sulfoxide.
Ampholytic synthetic detergents 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 substituents contains from about to about 20 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, phosphinate, or phosphonate, Examples of compounds falling within this definition are sodium 3-dodecylaminopropiqnate, sodium 3-(N-methyl-N-hexadecylamino)-2-hydroxypropane-l-sulfonate and its dodecyl homolog, sodium 3-dodecylaminopropane-l-sulfonate, sodium dodecyl-beta-alanine, sodium N-alkyltaurines such as the one prepared by reacting dodecylamine with sodium isethionate according to the teaching of United States Letters Patent No. 2,658,072, N-higher alkyl aspartic acids such as those produced according to the teaching of United States Letters Patent No. 2,438,091, and the products sold under the trade name Miranol and described in United States Letters Patent No. 2,528,378.
Zwitterionic synthetic detergents can be broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radical may be straight chain or branched, and wherein one of the aliphatic substituents contains from about 10 to about 20 carbon atoms and one contains an anionic water solubilization group, e.g., carboxy, sulfonate, sulfate, phosphate, phosphinate, or phosphonate. Examples of compounds falling within this definition are: 3 (N,N-dimethyl-N-hexadecylammonio)-2-hydroxypropane-l-sulfonate and the corresponding dodecyl and tetradecyl homologs and 3 (N,N-dimethyl-N-dodecylammonio)-propane-1-sulfonate and the corresponding hexadecyl and tetradecyl homologs.
It is also possible according to the present invention to use the present reversed zwitterionic detergents in combination with anionic brighteners. A detergent composition employing the combination of ingredients ordinarily can contain from about 0.01% by weight to about 2% by weight optical brightener. Examples of anionic optical brighteners which can be used herein are sodium 2-sulfo- 4-(2-naptho-1,2-triazolyl)stilbene and sodium 4,4-bis(4- anilino-6-morpholino s triazo-Z-ylamino)-2,2'-stilbene disulfonate.
The detergent compositions of this invention can also contain any of the usual adjuvants, diluents, and additives, for example, perfumes, anti-tarnishing agents, bacteriostatic agents, dyes, suds builders, suds depressors, and the like, without detracting from the advantageous properties of the composition.
The following examples illustrate detergent compositions containing the reversed zwitterionic compounds of this invention which can be used under .conditions of ordinary usage to clean, for example, soiled clothing or dishes. All percentages herein are by weight unless otherwise specified.
EXAMPLE IV Solidgranules Percent 2-(trimethylammonio)ethyl dodecylphosphonate 17.5 Sodium tripolyphosphate 50.0 Sodium silicate (Na O:SiO =1:2.5) 10.0 Sodium sulfate 17.5
Moisture 5.0
EXAMPLE v Compressed granulestablet Percent 2-(trimethylammonio)ethyl dodecylphosphate 31.0 Tetrasodium pyrophosphate 52.0 Trisodium phosphate 10.0 Moisture 7.0
EXAMPLE VI Solid-granules Percent 2-(trimethylammonio)ethyl dodecylphosphinate 32.0 Pentasodium ethane-l-hydroxy-l,1,2-triphosphonate 64.0
Moisture 4.0
EXAMPLE VII Solid-granules Percent 3 (N,N-dimethyl-N-hexadecylammonio 2 hydroxypropane 1 sulfonate 20.0 2-dimethylsulfonio)ethyl dodecylphosphinate 25.0 Sodium tripolyphosphate 35.0 Sodium carbonate 10.0 Sodium silicate (Na O:SiO =1:2.5) 5.0 Moisture 5.0
EXAMPLE VIII Solidgranules Percent 3-(trimethylammonio)propyl octadecylphosphonate 20.0 Sodium tallow alcohol sulfate 10.0 Trisodium ethane 1 hydroxy-l,l-diphosphonate 20.0 Sodium tripolyphosphate 10.0 Sodium nitrolotriacetate 10.0 Sodium sulfate 8.0 Sodium silicate (Na O:SiO =1:2.5) 11.0 Moisture 11.0
EXAMPLE IX Liquid Percent 2-(dimethylsulfonio)ethyl decylphosphonate 5.0 Sodium salt of S0 sulfonated 1:1 weight mixture of alpha-dodecene and alpha-tetradecene 10.0 Tetrapotassium pyrophosphate 19.0 Sodium silicate (NflzOZSiOg=1I1-6) 3.8 Potassium toluene sulfonate 8.5 Carboxymethyl hydroxyethyl cellulose .3 Water Balance 15 EXAMPLE X Liquid Percent 2-(dicthylsulfonio)ethyl decylphosphate 6.0 Sodium (linear) dodecyl benzene sulfonate 6.0
Tetrapotassium propane-1,l,3,3-tetraphosphonate 20.0
Sodium silicate (Na O:SiO =1:1.6) 3.8 Potassium toluene sulfonate 8.5 Carboxymethyl hydroxymethyl cellulose .3 Water Balance EXAMPLE XI Solidgranules Percent 2-(dimethylammonio)ethyl dodecylphosphonate 5.0 Condensation product of moles of ethylene oxide and one mole of tallow fatty alcohol 5.0
Sodium (linear) tridecyl benzene sulfonate 10.0
It will be appreciated that the reversed zwitterionic compounds used in the present invention can be incorporated into many other liquid or granular detergent compositions with suitable adjustments being made in the other components.
Materials which are considered normal and desirable additives in liquid or granule detergent compositions can be added to the compositions of this invention without adversely afiecting or modifying basic cleaning characteristics. For example, a tarnish inhibitor such as benzotriazole or ethylene thiourea may be added in amounts up to about 1%. Fluorescers, perfume, gleachingageu color, antiredeposition agents, antibacterial agents, thic ening agents,
opacifiers, and blending or viscosity control agen'sywhi le not essential in the compositions of this invention, mi}! also be added.
The compositions of the present invention can be used in conjunction with cool water washing situations as well as with warm and hot water.
What is claimed herein is:
1. A reversed zwitterionic detergent compound havin the formula R--Z-R --X wherein R is seected from alkyl and alkenyl of from about 10 to about 20 carbon atoms; Z is a negatively charged radical selected from the group consisting of phosphate, phosphonate, and phosphinate radicals; R is an alkylene radical containing from 2 to about 4 carbon atoms; and X is a positively charged radical selected from the group consisting of ammoniuin and tertiary sulfonium radicals; said ammonium radical having the formula wherein R R and R are each selected from the group consisting of hydrogen, methyl, and ethyl; said tertiary sulfonium radical having the formula as s RSRO wherein R and R are each selected from the group consisting of methyl and ethyl.
2. A reversed zwitterionic compound of claim 1 Wherein R has from about 12 to about 16 carbon atoms.
3. A reversed zwitterionic compound of claim 2 wherein R is an ethylene radical.
4. A reversed zwitterionic compound of claim 3 wherein Z is a phosphonate radical.
5. A reversed zwitterionic compound of claim 4 wherein X is a quaternary ammonium radical.
6. A reversed zwitterionic compound of claim 5 wherein R R and R are each methyl and R is dodecyl.
7. A reversed zwitterionic compound of claim 4 wherein R is dodecyl and X is ammonium wherein R is hydrogen and R and R are each methyl.
CHARLES B. PARKER, Primary Examiner A. H. SUTTO, Assistant Examiner U.S. Cl. X.R.
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US58409966A | 1966-10-04 | 1966-10-04 | |
US1030270A | 1970-02-10 | 1970-02-10 |
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US10302A Expired - Lifetime US3560393A (en) | 1966-10-04 | 1970-02-10 | Detergent compositions containing reversed zwitterionicc phosphorus compounds |
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Cited By (14)
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US3711493A (en) * | 1970-02-10 | 1973-01-16 | Ici Ltd | Plant growth regulating composition |
US3867482A (en) * | 1971-08-14 | 1975-02-18 | Basf Ag | 2-Chloroethanephosphonic acid derivatives |
US3870619A (en) * | 1973-01-29 | 1975-03-11 | Technic | Process for producing bright electrodeposits of gold and its alloys |
US3925453A (en) * | 1974-01-25 | 1975-12-09 | Monsanto Co | Quaternary aminoalkylene phosphonic acids and method of preparation |
US3928509A (en) * | 1973-04-14 | 1975-12-23 | Hoechst Ag | Hybrid ionic phosphorus compounds |
US4181634A (en) * | 1977-06-17 | 1980-01-01 | Johnson & Johnson | Mild cleansing compositions comprising an alkyleneoxylated bisquaternary ammonium compound and an anionic or amphoteric detergent such as a phosphobetaine |
US4263431A (en) * | 1978-05-29 | 1981-04-21 | Ciba-Geigy Corporation | Cationic fluorescent whitening agents |
US4384121A (en) * | 1979-11-01 | 1983-05-17 | Ciba-Geigy Corporation | Cationic fluorescent whitening agents |
EP0108565A2 (en) * | 1982-11-08 | 1984-05-16 | Takeda Chemical Industries, Ltd. | Phospholipids, their production and use thereof |
DE3506973A1 (en) * | 1984-03-01 | 1985-09-05 | Kao Corp., Tokio/Tokyo | PHOSPHORIC ACID ESTERS AND METHOD FOR THE PRODUCTION THEREOF |
US4542023A (en) * | 1983-02-01 | 1985-09-17 | Rhone-Poulenc Agrochimie | Fungicidal salts of organophosphorus derivatives |
FR2572078A1 (en) * | 1984-10-24 | 1986-04-25 | Inst Francais Du Petrole | Neutral phosphobetaines, their preparation and their application to the assisted recovery of oil |
WO2015120531A1 (en) * | 2013-02-19 | 2015-08-20 | Nano Safe Coatings Incorporated | Phosphonate functional antimicrobial coatings for metal surfaces |
US10961401B2 (en) | 2012-12-11 | 2021-03-30 | Nano Safe Coatings Incorporated | UV cured benzophenone terminated quaternary ammonium antimicrobials for surfaces |
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AU1092276A (en) * | 1975-02-14 | 1977-08-18 | Procter & Gamble | Detergent compositions |
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US3400148A (en) * | 1965-09-23 | 1968-09-03 | Procter & Gamble | Phosphonate compounds |
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- 1966-10-04 US US584099A patent/US3507937A/en not_active Expired - Lifetime
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- 1970-02-10 US US10302A patent/US3560393A/en not_active Expired - Lifetime
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US3400148A (en) * | 1965-09-23 | 1968-09-03 | Procter & Gamble | Phosphonate compounds |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
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US3711493A (en) * | 1970-02-10 | 1973-01-16 | Ici Ltd | Plant growth regulating composition |
US3867482A (en) * | 1971-08-14 | 1975-02-18 | Basf Ag | 2-Chloroethanephosphonic acid derivatives |
US3870619A (en) * | 1973-01-29 | 1975-03-11 | Technic | Process for producing bright electrodeposits of gold and its alloys |
US3928509A (en) * | 1973-04-14 | 1975-12-23 | Hoechst Ag | Hybrid ionic phosphorus compounds |
US3925453A (en) * | 1974-01-25 | 1975-12-09 | Monsanto Co | Quaternary aminoalkylene phosphonic acids and method of preparation |
US4181634A (en) * | 1977-06-17 | 1980-01-01 | Johnson & Johnson | Mild cleansing compositions comprising an alkyleneoxylated bisquaternary ammonium compound and an anionic or amphoteric detergent such as a phosphobetaine |
US4263431A (en) * | 1978-05-29 | 1981-04-21 | Ciba-Geigy Corporation | Cationic fluorescent whitening agents |
US4384121A (en) * | 1979-11-01 | 1983-05-17 | Ciba-Geigy Corporation | Cationic fluorescent whitening agents |
US4432886A (en) * | 1979-11-01 | 1984-02-21 | Ciba-Geigy Corporation | Cationic fluorescent whitening agents |
US4433975A (en) | 1979-11-01 | 1984-02-28 | Ciba-Geigy Corporation | Cationic fluorescent whitening agents |
EP0108565A2 (en) * | 1982-11-08 | 1984-05-16 | Takeda Chemical Industries, Ltd. | Phospholipids, their production and use thereof |
EP0108565A3 (en) * | 1982-11-08 | 1984-11-28 | Takeda Chemical Industries, Ltd. | Phospholipids, their production and use thereof |
US4542023A (en) * | 1983-02-01 | 1985-09-17 | Rhone-Poulenc Agrochimie | Fungicidal salts of organophosphorus derivatives |
US4623743A (en) | 1984-01-03 | 1986-11-18 | Kao Corporation | Phosphoric esters and method for preparing the same |
DE3506973A1 (en) * | 1984-03-01 | 1985-09-05 | Kao Corp., Tokio/Tokyo | PHOSPHORIC ACID ESTERS AND METHOD FOR THE PRODUCTION THEREOF |
FR2560599A1 (en) * | 1984-03-01 | 1985-09-06 | Kao Corp | PHOSPHORIC ESTERS AND PROCESS FOR THEIR PREPARATION |
FR2572078A1 (en) * | 1984-10-24 | 1986-04-25 | Inst Francais Du Petrole | Neutral phosphobetaines, their preparation and their application to the assisted recovery of oil |
US10961401B2 (en) | 2012-12-11 | 2021-03-30 | Nano Safe Coatings Incorporated | UV cured benzophenone terminated quaternary ammonium antimicrobials for surfaces |
WO2015120531A1 (en) * | 2013-02-19 | 2015-08-20 | Nano Safe Coatings Incorporated | Phosphonate functional antimicrobial coatings for metal surfaces |
US10154668B2 (en) | 2013-02-19 | 2018-12-18 | Nano Safe Coatings Incorporated | Phosphonate functional antimicrobial coatings for metal surfaces |
US10327447B2 (en) | 2013-02-19 | 2019-06-25 | Nano Safe Coatings Incorporated | Phosphonate functional antimicrobial coatings for metal surfaces |
USRE48510E1 (en) | 2013-02-19 | 2021-04-13 | Nano Safe Coatings Incorporated | Phosphorus functional antimicrobial coatings for metal surfaces |
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US3560393A (en) | 1971-02-02 |
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