US3255116A - Sulfoximine-containing detergent compositions - Google Patents
Sulfoximine-containing detergent compositions Download PDFInfo
- Publication number
- US3255116A US3255116A US404501A US40450164A US3255116A US 3255116 A US3255116 A US 3255116A US 404501 A US404501 A US 404501A US 40450164 A US40450164 A US 40450164A US 3255116 A US3255116 A US 3255116A
- Authority
- US
- United States
- Prior art keywords
- sulfoximine
- sodium
- detergent
- methyl
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003599 detergent Substances 0.000 title claims description 68
- 239000000203 mixture Substances 0.000 title claims description 48
- 125000005555 sulfoximide group Chemical group 0.000 title description 26
- 150000001875 compounds Chemical class 0.000 claims description 32
- 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 claims description 19
- 229910052708 sodium Inorganic materials 0.000 claims description 19
- 239000011734 sodium Substances 0.000 claims description 19
- 239000007844 bleaching agent Substances 0.000 claims description 8
- 229960001922 sodium perborate Drugs 0.000 claims description 5
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims description 5
- MMCOUVMKNAHQOY-UHFFFAOYSA-L oxido carbonate Chemical compound [O-]OC([O-])=O MMCOUVMKNAHQOY-UHFFFAOYSA-L 0.000 claims description 3
- MPNNOLHYOHFJKL-UHFFFAOYSA-K peroxyphosphate Chemical compound [O-]OP([O-])([O-])=O MPNNOLHYOHFJKL-UHFFFAOYSA-K 0.000 claims description 3
- HDMGAZBPFLDBCX-UHFFFAOYSA-M potassium;sulfooxy sulfate Chemical compound [K+].OS(=O)(=O)OOS([O-])(=O)=O HDMGAZBPFLDBCX-UHFFFAOYSA-M 0.000 claims description 3
- FOTNEEVHXTXVFX-UHFFFAOYSA-M sodium;benzenecarboperoxoate Chemical compound [Na+].[O-]OC(=O)C1=CC=CC=C1 FOTNEEVHXTXVFX-UHFFFAOYSA-M 0.000 claims description 3
- -1 aliphatic radical Chemical group 0.000 description 54
- 150000003839 salts Chemical class 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000007788 liquid Substances 0.000 description 10
- GMGBMACZCKHHJK-UHFFFAOYSA-N dodecyl-imino-methyl-oxo-$l^{6}-sulfane Chemical compound CCCCCCCCCCCCS(C)(=N)=O GMGBMACZCKHHJK-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 238000004900 laundering Methods 0.000 description 6
- 239000003352 sequestering agent Substances 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 235000019832 sodium triphosphate Nutrition 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 125000002252 acyl group Chemical group 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000004115 Sodium Silicate Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- 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 3
- CJPDBKNETSCHCH-UHFFFAOYSA-N 1-methylsulfinyldodecane Chemical compound CCCCCCCCCCCCS(C)=O CJPDBKNETSCHCH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 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 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
- 239000012065 filter cake Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 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 2
- 229940048086 sodium pyrophosphate Drugs 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 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 2
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- NZJXADCEESMBPW-UHFFFAOYSA-N 1-methylsulfinyldecane Chemical compound CCCCCCCCCCS(C)=O NZJXADCEESMBPW-UHFFFAOYSA-N 0.000 description 1
- KRUABTDBQQLWLS-UHFFFAOYSA-N 1-methylsulfinyltetradecane Chemical compound CCCCCCCCCCCCCCS(C)=O KRUABTDBQQLWLS-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
- JHWLWOYSFJIYQV-UHFFFAOYSA-N 4-dodecylbenzenesulfonate;tris(2-hydroxyethyl)azanium Chemical compound OCC[NH+](CCO)CCO.CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 JHWLWOYSFJIYQV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- FUHHUWFEESOUPY-UHFFFAOYSA-N CCS(=N)=O Chemical compound CCS(=N)=O FUHHUWFEESOUPY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound 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
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 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
- 229920000388 Polyphosphate Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 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 compound [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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004851 dishwashing Methods 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
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-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
- 239000000975 dye Substances 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 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
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 235000007686 potassium Nutrition 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
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229940083982 sodium phytate Drugs 0.000 description 1
- 229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
- 235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005494 tarnishing Methods 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 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
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 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
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000003981 vehicle 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
- C11D1/002—Surface-active compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/06—Phosphates, including polyphosphates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
Definitions
- This invention relates to a novel class of organic sulfur containing detergent compounds. More especially this invention relates to unsymmetrical sulfoximine compounds which are valuable detergent surfactants and to detergency compositions containing such compounds.
- an active detergent material is compatable with the many adjuvants and additives that are frequently incorporated into detergent formulations, including bleaches and other oxidizing media.
- novel sulfoximine compounds of this invention have been discovered to be thermally stable and resistant to hydrolysis in basic solutions. Furthermore, sulfoximine compounds of this invention are resistant to further oxidation, unlike the somewhat related sulfoxide detergents which show a propensity to undergo further oxi- Thus unlike the sulfoxides, the novel sulfoximine compounds of this invention can be used advantageously in detergent formulations containing peroxygen bleaches, or in other oxidizing media.
- Bleaching agents for example those of the peroxygen type, are often used in connection with detergents in the Occasionally in household situations a consumer will add a bleaching agent to a washing solution to aid in the cleaning process. This can easily result in the unintentional inactivation of the detergent compound unless the detergent compound is resistant to such bleaching agents. It is clearly an advantage therefore to have a detergent active that can be used along with such bleaching agents without themselves being transformed into an inactive form.
- novel sulfoximine compounds of this invention have the following formula:
- R is an aliphatic radical selected from the group consisting of straight chain, branched chain, saturated and unsaturated alkyl and alkenyl radicals having from 10 to about 18 carbon atoms, and wherein R is an alkyl radical selected from the group consisting of methyl and ethyl radicals.
- the long chain aliphatic substituent as defined above can be a straight chain, branched chain, saturated or unsaturated aliphatic radical having from 10 to about 18 carbon atoms. Examples are given hereinafter.
- the long chain aliphatic substituent can suitably be obtained from synthetic or natural sources such as coconut oil fatty alcohol which contains a mixture of alkyl and alkenyl radicals having predominantly a carbon chain length within the prescribed range.
- Examples of sulfoximine detergent compounds provided -by this invention include the following: decyl methyl sulfoximine, dodecyl methyl sulfoximine, tetradecyl methyl sulfoximine, octadecyl methyl sulfoximine, decyl ethyl sulfoximine, dodecyl ethyl sulfoximine, tetradecyl ethyl sulfoximine, hexadeeyl ethyl sulfoximine, octadecyl ethyl sulfoximine, 2-methyl undecyl methyl sulfoximine, tetrapropylene methyl sulfoximine, dodecenyl methyl sulfoximine and tetradecenyl ethyl sulfoximine.
- Short chain sulfoximine compounds are known in the prior art. It has never been recognized heretofore, however, that the particular unsymmetrical sulfoximine compounds of this invention have the highly desirable properties for use as detergents in the manner previously set forth.
- the sulfoximine compounds which have the necessary properties to be good detergent compounds are those which can be termed unsymmetrical sulfoximines.
- unsymmetrical is meant those sulfoximines in which one aliphatic group is quite long with respect to the other.
- the short alkyl group should contain no more than two carbon atoms, while the long alkyl chain should contain ten or more carbon atoms. If less than ten carbons are present in the long chain aliphatic hydrocarbon radical, cleaning effectiveness of the compound is seriously impaired.
- the higher aliphatic radical must contain more than ten carbon atoms, e.g. to 10 to 18 or 20 carbon atoms.
- the most preferred unsymmetrical sulfoximine compounds are the C -C alkyl methyl sulfoximines. Particularly desirable are the C -C alkyl methyl sulfoximine compounds.
- the filter cake methyldodecylsulfoximinium sulfate, weighed about 21 g. (71% yield). It was purified by recrystallization from acetone-ethanol or chloroformhexane, to M.P. 128-30.
- homologous members of the novel class of compounds can be prepared.
- decyl methyl sulfoxide was used, and essentially the same procedure followed, decyl methyl sulfoximine was recovered in a yield of 25.5%.
- the compound had a melting point of 51 C.
- Tetradecyl methyl sulfoximine was prepared according to the previous example by using tetradecyl methyl sulfoxide as a starting material. The compound yield was 61% and the compound had a melting point of 60 C.
- the dodecyl, decyl and tetradecyl methyl sulfoximines prepared in the manner described above can be used in detergent compositions as hereinafter described.
- Granular detergent compositions preferably contain about 5% to about 50% of the sulfoximine compounds of this invention and liquid formulations preferably contain about 2% to about of such sulfoximines.
- Granular detergent compositions preferably contain at least an equal amount of an alkaline builder salt.
- Liquid formulations preferably contain from about 5% to about of a water soluble alkaline builder salt, the balance of the composition being a solvent such as water, and/ or other liquid vehicles.
- Water-soluble inorganic alkaline builder salts which can be used alone with the detergent compound or in admixture with other builders are alkali metal carbonates, borates, phosphates, polyphosphates, bicarbonates and silicates. (Ammonium or substituted ammonium salts can also be used.) Specific examples of such salts are sodium tripolyphosphate, sodium carbonate, sodium tetraborate, sodium pyrophosphate, potassium pyrophosphate, sodium bicarbonate, potassium tripolyphosphate, sodium hexametahosphate, sodium sesquicarbonate, sodium monoand di-ortho phosphate and potassium bicarbonate. Potassium pyrophosphate finds wide application especially in built liquid detergent compositions.
- organic alkaline sequestrant builder salts which can be used alone with the detergent or in admixture with other organic and inorganic builders are alkali metal, ammonium or substituted ammonium, aminopolycarboxylates, e.g. sodium and potassium ethylenediaminetetraacetate, sodium and potassium N-(2-hydroxyethyl)- ethylenediaminetriacetates, sodium and potassium nitrilotriacetates and sodium, potassium and triethanolammonium N-(Z-hydroxyethyl)-nitrilo diacetates. 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 US. Patent 2,739,942).
- the unsymmetrical sulfoximine detergent compounds may be used as the sole detergent agent or they may be mixed with other well known detergent compounds such as anionic and nonionic detergent compounds.
- water-soluble salts the sodium, potassium, ammonium, and alkylolammonium salts, for example.
- Specific examples are: sodium lauryl sulfate; potassium N-methyl lauroyl tauride; triethanolammonium dodecylbenzene sulfonate.
- nonionic organic detergents which can be used in the compositions of this invention if desired are: polyethylene oxide condensates of alkyl phenols wherein the alkyl group contains from 6 to 12 carbon atoms (e.g. t-octylphenol and the ethylene oxide is present in a molar ratio of ethylene oxide to alkyl phenol in the range of 10:1 to 25:1; condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine wherein the molecular weight of the condensation products ranges from 5,000 to 11,000; the condensation products of from 5 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. lauryl alcohol); C -C alkyl di-(C C alkyl) amine oxides (e.g. dodecyl dimethyl amine oxide).
- Preferred liquid detergent compositions contain about 2 to about 30% of the sulfoximine compounds of the invention and about 5% to about 40% potassium pyrophosphate.
- the G -C alkyl methyl sulfoximines are used in such preferred compositions.
- Particularly desirable in built liquid compositions is dodecyl methyl sulfoximine.
- the detergent compositions of this invention can contain any of the usual adjuvants, diluents and additives, for example, ampholytic, cationic or zwitterionic detergents, perfumes, anti-tarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fiuorescers, suds builders, suds depressors and the like, without detracting from the advantageous properties of the composition.
- adjuvants for example, ampholytic, cationic or zwitterionic detergents, perfumes, anti-tarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fiuorescers, suds builders, suds depressors and the like, without detracting from the advantageous properties of the composition.
- the above-described sulfoximine compounds are efficient solubilizers and dispersers of calcium soap as well as being hydrolytically stable in base solution and resistant to oxidation from peroxygen type bleaches.
- peroxygen type bleaches which can be employed with the novel sulfoximine detergent compounds of this invention are sodium perborate, sodium perbenzoate, sodium perlaurate, sodium perazelate, sodium persebacate, peroxyphosphate, peroxycarbonate and Oxone," which is a potassium hydrogen persulfate bleach.
- bleaching agents can be incorporated into a detergent composition or be added during the washing cycle. Hydrogen peroxide can also be used during the washing cycle.
- the peroxygen bleaches may comprise from about 3% to about 15% by weight of the composition and preferably from 5% to about Cleansing and laundering compositions prepared according to this invention which can be used in the usual household laundering situations can contain from about 2% to 50% by weight of the unsymmetrical sulfoximine detergent compounds, 25% to 80% by weight of sodium tripolyphosphate or other previously mentioned builder, 12% to 45% by weight of sodium sulfate, 0% to 15% by weight of sodium silicate and 0% to about 40% by weight of water.
- An aqueous solution containing from about .15% to An aqueous solution containing from about 0.15% to 0.45% concentration of the above formula provides effective cleaning results in both laundering and dishwashing situations.
- a detergent composition consisting essentially of an unsymmetrical sulfoximine detergent compound having the following general formula:
- R-s-R' I l-H wherein R is an aliphatic radical selected from the group consisting of straight or branched chain saturated alkyl radicals having from 10 to about 18 carbon atoms, and wherein R is an alkyl radical selected from the group consisting of methyl and ethyl radicals, and a builder material selected from the group consisting of water-soluble inorganic alkaline builder salts, organic alkaline sequestrant builder salts and mixtures thereof, wherein the ratio of said detergent to said builder is in the range of 3:1 to about 1:10 by weight.
- the detergent composition of claim 1 including from about 3% -to about 15% by weight of a peroxygen type bleach selected from the group consisting of sodium per borate, sodium perbenzoate, sodium perlaurate, sodium perazelate, sodium persebacate, peroxyphosphate, peroxycarbonate, and potassium hydrogen persulfate.
- a peroxygen type bleach selected from the group consisting of sodium per borate, sodium perbenzoate, sodium perlaurate, sodium perazelate, sodium persebacate, peroxyphosphate, peroxycarbonate, and potassium hydrogen persulfate.
- a laundering and detergent composition consisting essentially of an active detergent compound an unsymmetrical alkyl methyl sulfoximine compound, wherein the alkyl radical contains from 10 to about 18 carbon atoms, and a builder salt selected from the group consisting of water-soluble inorganic alkaline builder salts, organic alkaline sequestrant builder salts and mixtures thereof, the ratio of said detergent compound to said builder salt being in the range of about 3:1 to about 1:10 by weight.
- a built liquid detergent composition consisting essentially of from about 2% to about 30% of the unsymmetrical sulfoximine detergent compound having the following general formula:
- R is an aliphatic radical selected from the group consisting of straight or branched chain saturated alkyl radicals having from 10 to about 18 carbon atoms
- R' is an alkyl radical selected from the group consisting of methyl and ethyl radicals, from about 5% to about 40% of a builder salt selected from the group consisting of water-soluble inorganic alkaline builder salts, water-soluble organic alkaline sequestrant builder salts, and mixtures thereof, the balance of the composition being water.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Detergent Compositions (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL302101D NL302101A (enrdf_load_stackoverflow) | 1962-12-26 | ||
| FR957507A FR1377794A (fr) | 1962-12-26 | 1963-12-17 | Composés détergents sulfoximines et compositions renfermant ceux-ci |
| BE641766A BE641766A (enrdf_load_stackoverflow) | 1962-12-26 | 1963-12-24 | |
| DEP33275A DE1225330B (de) | 1962-12-26 | 1963-12-24 | Reinigungsmittel |
| US404501A US3255116A (en) | 1962-12-26 | 1964-10-16 | Sulfoximine-containing detergent compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24731462A | 1962-12-26 | 1962-12-26 | |
| US404501A US3255116A (en) | 1962-12-26 | 1964-10-16 | Sulfoximine-containing detergent compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3255116A true US3255116A (en) | 1966-06-07 |
Family
ID=26938592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US404501A Expired - Lifetime US3255116A (en) | 1962-12-26 | 1964-10-16 | Sulfoximine-containing detergent compositions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3255116A (enrdf_load_stackoverflow) |
| BE (1) | BE641766A (enrdf_load_stackoverflow) |
| DE (1) | DE1225330B (enrdf_load_stackoverflow) |
| NL (1) | NL302101A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3376338A (en) * | 1965-09-01 | 1968-04-02 | Chevron Res | Sulfoximines |
| US3535240A (en) * | 1967-08-24 | 1970-10-20 | Procter & Gamble | Sulfoximine corrosion inhibitor for acid solutions |
| US4113738A (en) * | 1977-02-02 | 1978-09-12 | Polaroid Corporation | Conversion of N-tosylsulfoximides to sulfoximines |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2787595A (en) * | 1955-07-11 | 1957-04-02 | Union Oil Co | Sulfoxide containing detergent compositions |
| US2925442A (en) * | 1958-07-16 | 1960-02-16 | Crown Zellerbach Corp | Process for the oxidation of organic sulfides |
| DE1086165B (de) * | 1955-01-28 | 1960-07-28 | Wistra Ofenbau | Verfahren zum Betrieb eines gas- oder oelbeheizten Schachtofens |
| US3058916A (en) * | 1956-06-28 | 1962-10-16 | Henkel & Cie Gmbh | Colored cleaning agents |
| US3130165A (en) * | 1961-08-31 | 1964-04-21 | Procter & Gamble | Inorganic peroxy-compounds containing organic activators |
-
0
- NL NL302101D patent/NL302101A/xx unknown
-
1963
- 1963-12-24 BE BE641766A patent/BE641766A/xx unknown
- 1963-12-24 DE DEP33275A patent/DE1225330B/de active Pending
-
1964
- 1964-10-16 US US404501A patent/US3255116A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1086165B (de) * | 1955-01-28 | 1960-07-28 | Wistra Ofenbau | Verfahren zum Betrieb eines gas- oder oelbeheizten Schachtofens |
| US2787595A (en) * | 1955-07-11 | 1957-04-02 | Union Oil Co | Sulfoxide containing detergent compositions |
| US3058916A (en) * | 1956-06-28 | 1962-10-16 | Henkel & Cie Gmbh | Colored cleaning agents |
| US2925442A (en) * | 1958-07-16 | 1960-02-16 | Crown Zellerbach Corp | Process for the oxidation of organic sulfides |
| US3130165A (en) * | 1961-08-31 | 1964-04-21 | Procter & Gamble | Inorganic peroxy-compounds containing organic activators |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3376338A (en) * | 1965-09-01 | 1968-04-02 | Chevron Res | Sulfoximines |
| US3535240A (en) * | 1967-08-24 | 1970-10-20 | Procter & Gamble | Sulfoximine corrosion inhibitor for acid solutions |
| US4113738A (en) * | 1977-02-02 | 1978-09-12 | Polaroid Corporation | Conversion of N-tosylsulfoximides to sulfoximines |
Also Published As
| Publication number | Publication date |
|---|---|
| NL302101A (enrdf_load_stackoverflow) | |
| DE1225330B (de) | 1966-09-22 |
| BE641766A (enrdf_load_stackoverflow) | 1964-04-16 |
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