US3450637A - Detergent containing hydroxy alkyl amine oxide - Google Patents
Detergent containing hydroxy alkyl amine oxide Download PDFInfo
- Publication number
- US3450637A US3450637A US726609A US3450637DA US3450637A US 3450637 A US3450637 A US 3450637A US 726609 A US726609 A US 726609A US 3450637D A US3450637D A US 3450637DA US 3450637 A US3450637 A US 3450637A
- Authority
- US
- United States
- Prior art keywords
- oxide
- dimethyl
- amine
- sodium
- detergent
- 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 description 46
- 125000002768 hydroxyalkyl group Chemical group 0.000 title 1
- -1 Hydroxy alkylamine Chemical class 0.000 description 37
- 239000000203 mixture Substances 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 23
- 150000001412 amines Chemical class 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 18
- 150000003512 tertiary amines Chemical class 0.000 description 16
- 239000000344 soap Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 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 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 5
- 238000007654 immersion Methods 0.000 description 5
- 239000003352 sequestering agent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 4
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 235000019832 sodium triphosphate Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 4
- 241000700198 Cavia Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 125000005270 trialkylamine group Chemical group 0.000 description 3
- REICWNSBQADONN-UHFFFAOYSA-N 2-hydroxy-n,n-dimethyldodecan-1-amine oxide Chemical group CCCCCCCCCCC(O)C[N+](C)(C)[O-] REICWNSBQADONN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric 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
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920005646 polycarboxylate Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000004094 surface-active agent 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
- 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
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- LUDUPOQAFMTXBV-UHFFFAOYSA-N 1-(dimethylamino)-3-dodecoxypropan-2-ol Chemical compound CCCCCCCCCCCCOCC(O)CN(C)C LUDUPOQAFMTXBV-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- MEAWOXZXHLIEFZ-UHFFFAOYSA-N 2-hydroxy-N,N-dimethyltetradecan-1-amine oxide Chemical compound C[N+](CC(CCCCCCCCCCCC)O)(C)[O-] MEAWOXZXHLIEFZ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WQBLUYWIHIJQKQ-UHFFFAOYSA-N 3-dodecoxy-2-hydroxy-n,n-dimethylpropan-1-amine oxide Chemical compound CCCCCCCCCCCCOCC(O)C[N+](C)(C)[O-] WQBLUYWIHIJQKQ-UHFFFAOYSA-N 0.000 description 1
- VVEUGRHVQGHLNT-UHFFFAOYSA-N 3-hydroxy-N,N-dimethyldodecan-1-amine oxide Chemical compound C[N+](CCC(CCCCCCCCC)O)(C)[O-] VVEUGRHVQGHLNT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-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
- JYXGIOKAKDAARW-UHFFFAOYSA-N N-(2-hydroxyethyl)iminodiacetic acid Chemical class OCCN(CC(O)=O)CC(O)=O JYXGIOKAKDAARW-UHFFFAOYSA-N 0.000 description 1
- IJHVZBOIETWUPQ-UHFFFAOYSA-N N-ethyl-3-hydroxy-N-methyldodecan-1-amine oxide Chemical compound C[N+](CCC(CCCCCCCCC)O)(CC)[O-] IJHVZBOIETWUPQ-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 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
- 239000004115 Sodium Silicate Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 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
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000704 physical effect Effects 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
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- 229940083982 sodium phytate Drugs 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 238000005494 tarnishing Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 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
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
- C11D1/66—Non-ionic compounds
- C11D1/75—Amino oxides
-
- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0047—Detergents in the form of bars or tablets
- C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
-
- 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 novel tertiary amine oxide detergents and detergent compositions containing them.
- Thermal stability is a highly desirable property which is lacking in many detergents. Such stability is particularly desirable when detergents are subjected to heat during use or processing, as for example, in spray drying granular detergent compositions.
- Another advantageous property for an organic detergent is a low degree of hygroscopicity which results in improved crystallinity.
- detergent surfactants which are hygroscopic are used in bar or granular forms, desirable physical properties are impaired. Bars become soft and slimy and granules tend to cake and lose their free flowing and quick dissolving characteristics.
- trialkylamine oxides have been found to be excellent detergent compounds but are so hygroscopic that they can be effectively used only in liquid detergent compositions.
- the amine oxides of this invention are:
- R is a 2-hydroxyalkyl, S-hydroxyalkyl or 3-alkoxy-2-hydroxypropyl radical in which the alkyl and alkoxy, respectively, range from to 18 carbon atoms in chain length, R and R are each methyl, ethyl, propyl or isopropyl.
- R R R N-90 The class of compounds described above lwill hereinafter be referred to more simply as R R R N-90.
- Examples of the compounds of this invention are dimethyl-Z-hydroxydodecylamine oxide, diethyl-3-hydroxydodecylamine oxide, dimethyl 2-hydroxytetradecylamine oxide, dipropyl-3-hydroxyhexadecylamine oxide, propylmethyl 2 hydroxyoctadecylamine oxide, diethyl-Z-hydroxyhexadecylamine oxide, diethyl-2-hydroxytetradecylamine oxide, diisopropyl-Z-hydroxydodecylamine oxide, N,N-dimethyl-3-dodecoxy-Z-hydroxypropylamine oxide, N,N-diethyl 3-tetradecoxy-2-hydroxypropylamine oxide and methylethyl-3-hydroxydodecylamine oxide.
- Tertiary amine oxides as a broad class of compounds are known. It was surprising to find, however, that the particular trialkylamine oxides containing particularlyplaced hydroxy groups as described above (i.e., a hydroxy group in the 2 or 3 position in R have such highly desirable properties for use as organic detergents, i.e., improved mildness, hygroscopicity and thermal stability characteristics.
- R R and R must be as described above. If the alkyl or alkoxy in R is longer in chain length than 18 carbon atoms or shorter in chain length than 10 carbon atoms, desired detergency is not obtained. Like,- wise, if R and R contain more than 3 carbon atoms, desired detergency characteristics are not obtained.
- the long chain R radical must contain a hydroxy group in the 2 or 3 position (i.e., the second or third carbon atom from the nitrogen) in order to achieve improved mildness, hygroscopicity and thermostability characteristics in accordance with this invention. When the hydroxy group in the R radical is in the 1 or alpha position, the resultant amine oxide compound has undesirable instability.
- the 3-alkoxy- Z-hydroxypropyl R radical has the following general formula:
- ROOHzCHCHz wherein R ranges from 10 to 18 carbon atoms in chain length.
- the Z-hydroxyalkyl, 3-hydroxyalkyl and the 3-alkoxy-2- hydroxypropyl compounds have about the same reduced hygroscopicity characteristics as compared to the corresponding compound containing unsubstituted R alkyl group.
- the 3-hydroxyalkyl compound has about the same water solubility as the corresponding compound containing an unsubstituted R alkyl group whereas the water solubility of the 2-hydroxyalkyl compound is somewhat less than the solubility of the corresponding compound containing an unsubstituted R group.
- R can be derived from naturally occurring fats and oils or [from synthetic sources such as olefins. Mixtures of amine oxides are very suitable wherein the alkyl or alkoxy in R varies in chain length in the C to C range, as for example, the alkyl or alkoxy groups derived from coconut fatty alcohol (or distilled coconut tfatty alcohol). Those amine oxides in which the alkyl or alkoxy in R ranges from 12 to 14 carbon atoms are preferred.
- the tertiary amine oxides of this invention can be prepared, in general, by oxidizing the corres onding tertiary amine. See, for example, British Patent 437,566.
- the corresponding tertiary amine in general, can be prepared by alkylating, with an appropriate long chain alkyl compound, the appropriate secondary amine. If necessary, the long chain alkyl compound can be such -(e.g., ketoalkane) that treatment (eg, reduction) of the tertiary amine, prior to oxidation, will result in hydroxy substitution at the desired location in the R group.
- treatment eg, reduction
- alkyl glycidyl ethers a source of the 3-alkoxy-2-hydroxypro- 3 pyl R is described in Canadian Patent 582,404, issued Sept. 1, 1959 and US. Patent 2,989,547, issued June 20, 1961.
- Compounds of this invention are useful per se as detergents and surface active agents. Desirably they are used with other materials to form detergent compositions, particularly solid form compositions as for example, bar, flake, granular or tableted granular compositions.
- the tertiary amine oxides of this invention can also be used to make liquid detergent compositions.
- Such detergent compositions can contain from about 5% to about 80% of the tertiary amine oxides of this invention and from about 95% to about 20% of anionic organic detergents, nonionic organic detergents, water-soluble inorganic alkaline builder salts, water-soluble organic alkaline sequestrant builder salts or mixtures thereof.
- Granular or flake detergents preferably contain about 5% to about 50% of the amine oxides of this invention and from about 95% to about 50% normally solid, watersoluble inorganic alkaline builder salts, or water-soluble organic alkaline sequestrant builder salts.
- Bar formulations contain about 5% to about 50% of the amine oxides of this invention when uhed with anionic detergents, such as a soap base, and, if desired, alkaline inorganic or organic builders or inert fillers.
- Bar formulations can contain about 40% to about 80% of the amine oxides of this invention as the only detergent component, if desired, and the balance inert fillers or builders.
- Anionic organic detergenets used alone or in admixture include both the soap and non-soap detergents.
- suitable soaps are the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids (C C Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.
- anionic organic non-soap detergents are: alkyl glyceryl ether sulfonates; alkyl sulfates; alkyl monoglyceride sulfates or sulfonates; alkyl polyethyenoxy ether sulfates; acyl sarcosinates; acyl esters of isethionates; acyl N-methyl taurides; alkylbenzenesulfonates; alkyl phenol polyethenoxy sulfonates.
- the alkyl and the acyl groups respectively, contain 10 to 20 carbon atoms.
- water-soluble salts the sodium, potassium, ammonium and alkylolammonium salts, for example.
- Specific examples are: sodium lauryl sulfate; potassium N-methyl lauroyl tauride; triethanolarnmonium dodecylbenzenesulammonium or substituted ammonium amino polycarboxylates, e.g., sodium and potassium ethylenediaminetetraacetate, sodium and potassium N-(2-hydroxyethyl)-ethylenediaminetriacetates, sodium and potassium nitrilotriacetates and sodium, potassium, and triethanolammonium N (2-hydroxyethyl)nitrilodiacetates.
- organic alkaline sequestrant builder salts which can be used are: Hydroxyethylethylenediaminetriacetates; 2 hydroxyethyliminodiacetates; diethylenetriaminepentaacetates; 1,2-diaminocyclohexanetetraacetates.
- the alkali metal salts of phytic acid, e.g., sodium phytate are also suitable as alkaline organic sequestrant builder salts (see US. Patent 2,739,942).
- Preferred detergent compositions contain about 10% to about 30% of the tertiary amine oxides of the invention and at least an equal amount of sodium tripolyphosphate.
- the amine oxides wherein the alkyl or alkoxy in R contains 12 to 14 carbon atoms are used in such preferred compositions.
- Particularly desirable is dimethyl- 2-hydroxydodecylamine oxide which has good sudsing characteristics, being superior in this respect to dimethyldodecylamine oxide. It also is an effective suds enhancing (building) agent for anionic non-soap detergent compounds.
- the detergent compositions of this invention can contain any of the usual adjuvants, diluents or additives, for example, ampholytic or zwitterionic detergents, cationic detergents, perfumes, anti-tarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fluorescers, oxygen or chlorine bleaches, suds builders, suds depressors and the like.
- adjuvants for example, ampholytic or zwitterionic detergents, cationic detergents, perfumes, anti-tarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fluorescers, oxygen or chlorine bleaches, suds builders, suds depressors and the like.
- EXAMPLE I 5 moles of dimethyl amine were liquified under anhydrous conditions using a Dry Ice-acetone condenser. 0.05 mole of anhydrous aluminum chloride was added to the dimethyl amine and a mixture was placed in a cold, glass autoclave liner (3 liter). One mole of C olefin oxide CmHmCH-CHg was added to the dimethylamine with mixing and cooling. The liner was placed in a cooled autoclave. After EXAMPLE II 170 grams of 2-undecanone, 22.5 grams of paraformaldehyde, 40.8 grams of dimethyl amine hydrochloride were mixed with 500 ml. of ethanol and stirred for 24 hours at 78 C.
- reaction mixture was acidified and extracted with ethyl ether to remove the unreacted 2-undecanone.
- the mixture was then made alkaline and extracted again with ethyl ether to obtain 81 grams of 3-ketododecyl dimethyl amine.
- the reaction is represented by the following equation:
- the resulting dimethyl-3-hydroxydodecyl amine oxide was tested for hygroscopicity, being compared with the 2-hydroxydodecyldimethyl amine oxide of Example I and with an unsubstituted dimethyldodecyl amine oxide.
- the hygroscopicity was determined by exposing dry recrystallized material in a constant 50% relative humidity chamber at 70 F.
- the dimethyl-3-hydroxydodecyl amine oxide and the dimethyl-Z-hydroxydodecyl amine oxide were tested for detergency properties. These amine oxides were substantially equivalent in detergency to sodium dodecylbenzenesulfonate.
- the determination was made by washing naturally soiled cloth (desized print cloth) swatches in an 0.1% aqueous solution of a mixture of 20% of an organic detergent compound (amine oxide being tested or alkylbenzenesulfonate standard) 50% sodium tripolyphosphate and 30% sodium sulfate.
- the composition had a pH of 10 and the washing was done at F. for 10 minutes using wash water of 7 grains per gallon hardness.
- the detergency effectiveness was determined by measuring the percentage of lipid soil remaining on a standard size swatch (on a dry basis) after the washing operation. The percentage of lipid soil remaining after washing with the amine oxide test composition was compared with the percentage after washing with the alkylbenzenesulfonate standard composition. On the basis of the percent residual lipid soil, the lower the percent, the better the detergency performance. A Tergotometer was used for the washing operation. (Tergotometer testing is described in Detergency Evaluation and Testing by J. C. Harris, Interscience Publishers, Inc.
- N,N-dimethyl-3-dodecoxy-2-hydroxypropylamine oxide absorbed only 0.3% water after one week of storage in an open vessel at room temperature and conditions. Only 22% water was absorbed upon extreme storage conditions of 90 F. and 80% relative humidity for 7 days. This amine oxide exhibited excellent detergency and sudsing characteristics and has excellent thermal stability.
- N,N-diethyl-3-tetradecoxy-2-hydroxypropylamine oxide and N,N dimethyl-3-hexadecoxy-2-hydroxypropylamine oxide can be prepared by processes similar to that described in Example II. These compounds have improved characteristics similar to those of the dodecyl compound.
- tertiary amine oxides of this invention can be used in effective detergent compositions having improved hygroscopicity and thermal stability characteristics. They have the following formulas:
- Granular detergent Sodium dodecylbenzenesulfonate (the dodecyl group being derived from tetrapropylene) 10 Sodium nitrilotriacetate 35 Sodium sulfate 40 Water Granular detergent Dipropyl-3-hydroxy tetradecyl amine oxide Condensation product of one mole of nonyl phenol and nine moles of ethylene oxide 10 Sodium pyrophosphate 50 Sodium carbonate 3 Trisodium phosphate 3 Sodium sulfate 24 Granular detergent Parts Dimethyl-Z-hydroxydodecylamine oxide 1 Potassium ethylenediaminetetraacetate 2 Granular detergent Parts Dimethyl-3-hydroxydodecylamine oxide 1 Potassium pyrophosphate 5 Spray-dried granular detergent Percent N,N-dimethyl-3-dodecoxy 2 hydroxypropylamine oxide Sodium dodecylbenzenesulfonate Sodium tripolyphosphate 50 Sodium s
- This test consists of immersing guinea pigs having shaved undersides up to their thorax in a 0.2% solution of the material being tested at 37 C., for a 4 /2 hour period per day for three consecutive days.
- the animals are graded three days after the last immersion.
- the grades are the average of the results on not less than three animals.
- a '1 to 10 scale is used to rate the efiects of the prolonged exposure of the test solution on the animals skin.
- Grade 10 represents ideal or perfect skin (soft, smooth and flexible) and the effect of a theoretically perfectly mild detergent compound; grade 1 represents severely irritated skin. Other values represent graduations of severity between these extremes.
- Grade 1 in the guinea pig immersion test indicates severely thickened, dry, cracked and bleeding skin, i.e., extreme irritation.
- Grade 1 in exaggerated tests on human subjects would indicate severe redness and dryness of the skin. Exaggerated exposure tests on guinea pigs are much more extreme than those conducted on human subjects.
- the guinea pig immersion test can be relied on to grade the relative mildness of detergent compounds toward the human skin.
- dimethyldodecylamine oxide had a grade of 2
- dimethyl-Z-hydroxydodecylamine oxide has a grade of 5.
- a detergent composition consisting essentially of from about 5% to about 80% of a tertiary amine oxide compound having the formula R R R N 0, wherein R is 2-hydroxyalkyl or 3-hydroxyalkyl in which the alkyl ranges in chain length from 10 to 18 carbon atoms and R and R are each methyl, ethyl, propyl or isopropyl and from about to about 20% of a material selected from the group consisting of water-soluble inorganic alkaline builder salts, water-soluble organic alkaline sequestrant builder salts, water-soluble soap, water-soluble synthetic organic non-soap anionic detergents and mixtures thereof.
- composition of claim 1 wherein the amine oxide is dimethyl-2-hydroxydodecylamine oxide.
- composition of claim 2 wherein the material is sodium tripolyphosphate.
- composition of claim 2 wherein the material is sodium dodecyl benzene sulfonate.
- composition of claim 1 wherein the amine oxide is dimet-hyl-3-hydroxydodecylamine oxide.
Description
United States Patent Int. Cl. C11d 7/24 US. Cl. 252--137 Claims ABSTRACT OF THE DISCLOSURE Hydroxy alkylamine oxide having improved hygroscopicity and thermal stability properties are employed in detergent composition containing alkaline builders or other synthetic detergents.
This is a division of Ser. No. 156,993 filed Dec. 4, 1961. This is a continuation of Ser. No. 324,181 filed Nov. 18, 1963, now abandoned.
This invention relates to novel tertiary amine oxide detergents and detergent compositions containing them.
In the constant improvement of organic detergent compounds, certain features have been found to be highly desirable. These features include resistance toward the ingredients imparting hardness to water, a high degree of detergency, and capacity for solubilization of hard water soaps, such as calcium soap. Although there are a number of organic detergents which have these characteristics, detergent compounds having additional desirable characteristics, find a wider scope of application.
Thermal stability is a highly desirable property which is lacking in many detergents. Such stability is particularly desirable when detergents are subjected to heat during use or processing, as for example, in spray drying granular detergent compositions.
Another advantageous property for an organic detergent is a low degree of hygroscopicity which results in improved crystallinity. When detergent surfactants which are hygroscopic are used in bar or granular forms, desirable physical properties are impaired. Bars become soft and slimy and granules tend to cake and lose their free flowing and quick dissolving characteristics. For example, trialkylamine oxides have been found to be excellent detergent compounds but are so hygroscopic that they can be effectively used only in liquid detergent compositions.
It is the object of this invention to provide organic detergents and detergent. compositions which have excellent detergency characteristics as well as improved mildness to the skin, improved thermal stability and a low degree of hygroscopicity.
It was found that these and other objects are achieved in a novel class of tertiary amine oxides having the structure set forth below and detergent compositions containing such compounds, preferably in solid form, as hereinafter more fully described. I
The amine oxides of this invention are:
In the above formulas R is a 2-hydroxyalkyl, S-hydroxyalkyl or 3-alkoxy-2-hydroxypropyl radical in which the alkyl and alkoxy, respectively, range from to 18 carbon atoms in chain length, R and R are each methyl, ethyl, propyl or isopropyl. The class of compounds described above lwill hereinafter be referred to more simply as R R R N-90.
Examples of the compounds of this invention are dimethyl-Z-hydroxydodecylamine oxide, diethyl-3-hydroxydodecylamine oxide, dimethyl 2-hydroxytetradecylamine oxide, dipropyl-3-hydroxyhexadecylamine oxide, propylmethyl 2 hydroxyoctadecylamine oxide, diethyl-Z-hydroxyhexadecylamine oxide, diethyl-2-hydroxytetradecylamine oxide, diisopropyl-Z-hydroxydodecylamine oxide, N,N-dimethyl-3-dodecoxy-Z-hydroxypropylamine oxide, N,N-diethyl 3-tetradecoxy-2-hydroxypropylamine oxide and methylethyl-3-hydroxydodecylamine oxide.
Tertiary amine oxides as a broad class of compounds are known. It was surprising to find, however, that the particular trialkylamine oxides containing particularlyplaced hydroxy groups as described above (i.e., a hydroxy group in the 2 or 3 position in R have such highly desirable properties for use as organic detergents, i.e., improved mildness, hygroscopicity and thermal stability characteristics.
It appears that only certain tertiary amine oxides have the aforementioned desirable characteristics; in these certain amine oxides, R R and R must be as described above. If the alkyl or alkoxy in R is longer in chain length than 18 carbon atoms or shorter in chain length than 10 carbon atoms, desired detergency is not obtained. Like,- wise, if R and R contain more than 3 carbon atoms, desired detergency characteristics are not obtained. The long chain R radical must contain a hydroxy group in the 2 or 3 position (i.e., the second or third carbon atom from the nitrogen) in order to achieve improved mildness, hygroscopicity and thermostability characteristics in accordance with this invention. When the hydroxy group in the R radical is in the 1 or alpha position, the resultant amine oxide compound has undesirable instability. The 3-alkoxy- Z-hydroxypropyl R radical has the following general formula:
ROOHzCHCHzwherein R ranges from 10 to 18 carbon atoms in chain length.
The Z-hydroxyalkyl, 3-hydroxyalkyl and the 3-alkoxy-2- hydroxypropyl compounds have about the same reduced hygroscopicity characteristics as compared to the corresponding compound containing unsubstituted R alkyl group. The 3-hydroxyalkyl compound has about the same water solubility as the corresponding compound containing an unsubstituted R alkyl group whereas the water solubility of the 2-hydroxyalkyl compound is somewhat less than the solubility of the corresponding compound containing an unsubstituted R group.
In tertiary amine oxides of this invention, R can be derived from naturally occurring fats and oils or [from synthetic sources such as olefins. Mixtures of amine oxides are very suitable wherein the alkyl or alkoxy in R varies in chain length in the C to C range, as for example, the alkyl or alkoxy groups derived from coconut fatty alcohol (or distilled coconut tfatty alcohol). Those amine oxides in which the alkyl or alkoxy in R ranges from 12 to 14 carbon atoms are preferred.
The tertiary amine oxides of this invention can be prepared, in general, by oxidizing the corres onding tertiary amine. See, for example, British Patent 437,566. The corresponding tertiary amine, in general, can be prepared by alkylating, with an appropriate long chain alkyl compound, the appropriate secondary amine. If necessary, the long chain alkyl compound can be such -(e.g., ketoalkane) that treatment (eg, reduction) of the tertiary amine, prior to oxidation, will result in hydroxy substitution at the desired location in the R group. The examples explain in detail such reactions. The preparation of alkyl glycidyl ethers (a source of the 3-alkoxy-2-hydroxypro- 3 pyl R is described in Canadian Patent 582,404, issued Sept. 1, 1959 and US. Patent 2,989,547, issued June 20, 1961.
Compounds of this invention are useful per se as detergents and surface active agents. Desirably they are used with other materials to form detergent compositions, particularly solid form compositions as for example, bar, flake, granular or tableted granular compositions. (The tertiary amine oxides of this invention can also be used to make liquid detergent compositions.) Such detergent compositions can contain from about 5% to about 80% of the tertiary amine oxides of this invention and from about 95% to about 20% of anionic organic detergents, nonionic organic detergents, water-soluble inorganic alkaline builder salts, water-soluble organic alkaline sequestrant builder salts or mixtures thereof.
Granular or flake detergents preferably contain about 5% to about 50% of the amine oxides of this invention and from about 95% to about 50% normally solid, watersoluble inorganic alkaline builder salts, or water-soluble organic alkaline sequestrant builder salts. Bar formulations contain about 5% to about 50% of the amine oxides of this invention when uhed with anionic detergents, such as a soap base, and, if desired, alkaline inorganic or organic builders or inert fillers. Bar formulations can contain about 40% to about 80% of the amine oxides of this invention as the only detergent component, if desired, and the balance inert fillers or builders.
Anionic organic detergenets used alone or in admixture include both the soap and non-soap detergents. Examples of suitable soaps are the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids (C C Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap. Examples of anionic organic non-soap detergents are: alkyl glyceryl ether sulfonates; alkyl sulfates; alkyl monoglyceride sulfates or sulfonates; alkyl polyethyenoxy ether sulfates; acyl sarcosinates; acyl esters of isethionates; acyl N-methyl taurides; alkylbenzenesulfonates; alkyl phenol polyethenoxy sulfonates. In these compounds the alkyl and the acyl groups, respectively, contain 10 to 20 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 lauryl sulfate; potassium N-methyl lauroyl tauride; triethanolarnmonium dodecylbenzenesulammonium or substituted ammonium amino polycarboxylates, e.g., sodium and potassium ethylenediaminetetraacetate, sodium and potassium N-(2-hydroxyethyl)-ethylenediaminetriacetates, sodium and potassium nitrilotriacetates and sodium, potassium, and triethanolammonium N (2-hydroxyethyl)nitrilodiacetates. Mixed salts of those polycarboxylates are also suitable. Other organic alkaline sequestrant builder salts which can be used are: Hydroxyethylethylenediaminetriacetates; 2 hydroxyethyliminodiacetates; diethylenetriaminepentaacetates; 1,2-diaminocyclohexanetetraacetates. The alkali metal salts of phytic acid, e.g., sodium phytate are also suitable as alkaline organic sequestrant builder salts (see US. Patent 2,739,942).
Preferred detergent compositions contain about 10% to about 30% of the tertiary amine oxides of the invention and at least an equal amount of sodium tripolyphosphate. Desirably the amine oxides wherein the alkyl or alkoxy in R contains 12 to 14 carbon atoms are used in such preferred compositions. Particularly desirable is dimethyl- 2-hydroxydodecylamine oxide which has good sudsing characteristics, being superior in this respect to dimethyldodecylamine oxide. It also is an effective suds enhancing (building) agent for anionic non-soap detergent compounds.
The detergent compositions of this invention can contain any of the usual adjuvants, diluents or additives, for example, ampholytic or zwitterionic detergents, cationic detergents, perfumes, anti-tarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fluorescers, oxygen or chlorine bleaches, suds builders, suds depressors and the like.
The following are examples which illustrate the tertiary amine oxide compounds and compositions of this invention.
EXAMPLE I 5 moles of dimethyl amine were liquified under anhydrous conditions using a Dry Ice-acetone condenser. 0.05 mole of anhydrous aluminum chloride was added to the dimethyl amine and a mixture was placed in a cold, glass autoclave liner (3 liter). One mole of C olefin oxide CmHmCH-CHg was added to the dimethylamine with mixing and cooling. The liner was placed in a cooled autoclave. After EXAMPLE II 170 grams of 2-undecanone, 22.5 grams of paraformaldehyde, 40.8 grams of dimethyl amine hydrochloride were mixed with 500 ml. of ethanol and stirred for 24 hours at 78 C. The reaction mixture was acidified and extracted with ethyl ether to remove the unreacted 2-undecanone. The mixture was then made alkaline and extracted again with ethyl ether to obtain 81 grams of 3-ketododecyl dimethyl amine. The reaction is represented by the following equation:
38 grams of LiAlH was dissolved in 600 ml. of anhydrous diethylether. 57 grams of the 3-keto dodecyl dimethyl amine obtained above was dissolved in 400 ml. of diethylether and added drop-wise to the LiAlH solution. This mixture was then stirred for an additional 1 /2 hours. The unreacted LiAlH was decomposed by the addition of ethyl acetate followed by water. The solution was filtered to remove solids. The filtrate split into aqueous and ether layers. The ether layer was evaporated on a steam bath to yield the hydroxy amine. This reaction is represented by the following equation:
Found Calculated 45 grams of the dimethyl-3-hydroxydodecyl amine obtained above, was mixed with 8.5 grams of hydrogen peroxide (28.5 grams of a 30% aqueous solution) and 250 ml. of ethanol and 125 ml. of water. This mixture was stirred for 6 hours at 50 C. After cooling to room temperature the solution was diluted with 400 ml. of water and the remaining peroxide decomposed catalytically. The unreacted amine was removed with a triple ether extraction. The ethanol was largely removed from solution on a steam bath and the product was isolated by freeze drying. The amine oxide was recrystallized from acetone and had the following element analysis.
Calculated (percent): C, 68.50; H, 12.73; N, 5.71. Found (percent): C, 67.89; H, 12.40; N, 5.67.
The resulting dimethyl-3-hydroxydodecyl amine oxide was tested for hygroscopicity, being compared with the 2-hydroxydodecyldimethyl amine oxide of Example I and with an unsubstituted dimethyldodecyl amine oxide. The hygroscopicity was determined by exposing dry recrystallized material in a constant 50% relative humidity chamber at 70 F.
-C 12H251IT( C He) 2 It is apparent that the 3-hydroxydodecyl and the 2-hydroxydodecyl compounds are markedly less hygroscopic than the unsubstituted dodecyl compound. The thermal stability of the compounds of this invention are indicated by decomposition temperatures of the 3-hydroxydodecyl and the 2-hydroxydodecyl compounds of 145 C. and 130 C. respectively as compared to C. decomposition temperature of unsubstituted dimethyldodecyl amine oxide.
The dimethyl-3-hydroxydodecyl amine oxide and the dimethyl-Z-hydroxydodecyl amine oxide were tested for detergency properties. These amine oxides were substantially equivalent in detergency to sodium dodecylbenzenesulfonate. The determination was made by washing naturally soiled cloth (desized print cloth) swatches in an 0.1% aqueous solution of a mixture of 20% of an organic detergent compound (amine oxide being tested or alkylbenzenesulfonate standard) 50% sodium tripolyphosphate and 30% sodium sulfate. The composition had a pH of 10 and the washing was done at F. for 10 minutes using wash water of 7 grains per gallon hardness. The detergency effectiveness was determined by measuring the percentage of lipid soil remaining on a standard size swatch (on a dry basis) after the washing operation. The percentage of lipid soil remaining after washing with the amine oxide test composition was compared with the percentage after washing with the alkylbenzenesulfonate standard composition. On the basis of the percent residual lipid soil, the lower the percent, the better the detergency performance. A Tergotometer was used for the washing operation. (Tergotometer testing is described in Detergency Evaluation and Testing by J. C. Harris, Interscience Publishers, Inc. (1954) page 60 Diethyl-2-hydroxytetradecylamine oxide, diisopropyl-3- hydroxyhexadecylamine oxide and dimethyl-Z-hydroxyalkylamino oxide wherein the alkyl is derived from coconut fatty alcohol can be made by processes similar to those described in Examples I and II. These compounds will have substantially equivalent thermal stability and hygroscopicity characteristics and the detergency efficacy will be slightly less than that of the hydroxydodecyl compounds.
EXAMPLE III 1,818 grams of dodecyl glycidyl ether was charged into a two liter autoclave. Air was purged from the head space with dimethyl amine. The autoclave Was then heated to 390 A pressure of 450 p.s.i. was obtained in the autoclave by charging dimethyl amine into the autoclave using nitrogen pressure. A dimethylamine bleed valve was adjusted during the reaction of the ether with the dimethyl amine to keep a constant pressure and temperature. After one hour, the autoclave was cooled. The resultant N,N-dimethyl 3 dodecoxy 2 hydroxypropylamine contained about 25% dissolved dimethylamine which was stripped off at F. at 5 mm. Hg pressure. The amination reaction is represented by the following equation:
1000 grams of this tertiary amine was mixed with 2789.3 grams of water, heated to 180 F. and mixed with 462 grams of 25% aqueous solution of hydrogen peroxide. The mixture was vigorously agitated. The resultant mixture was aged overnight at about 170 F. to decompose excess peroxide.
The resultant N,N-dimethyl-3-dodecoxy-2-hydroxypropylamine oxide absorbed only 0.3% water after one week of storage in an open vessel at room temperature and conditions. Only 22% water was absorbed upon extreme storage conditions of 90 F. and 80% relative humidity for 7 days. This amine oxide exhibited excellent detergency and sudsing characteristics and has excellent thermal stability.
N,N-diethyl-3-tetradecoxy-2-hydroxypropylamine oxide and N,N dimethyl-3-hexadecoxy-2-hydroxypropylamine oxide can be prepared by processes similar to that described in Example II. These compounds have improved characteristics similar to those of the dodecyl compound.
The tertiary amine oxides of this invention can be used in effective detergent compositions having improved hygroscopicity and thermal stability characteristics. They have the following formulas:
Granular detergent Sodium dodecylbenzenesulfonate (the dodecyl group being derived from tetrapropylene) 10 Sodium nitrilotriacetate 35 Sodium sulfate 40 Water Granular detergent Dipropyl-3-hydroxy tetradecyl amine oxide Condensation product of one mole of nonyl phenol and nine moles of ethylene oxide 10 Sodium pyrophosphate 50 Sodium carbonate 3 Trisodium phosphate 3 Sodium sulfate 24 Granular detergent Parts Dimethyl-Z-hydroxydodecylamine oxide 1 Potassium ethylenediaminetetraacetate 2 Granular detergent Parts Dimethyl-3-hydroxydodecylamine oxide 1 Potassium pyrophosphate 5 Spray-dried granular detergent Percent N,N-dimethyl-3-dodecoxy 2 hydroxypropylamine oxide Sodium dodecylbenzenesulfonate Sodium tripolyphosphate 50 Sodium sulfate 15 Sodium silicate 5 Moisture 10 Milled toilet bar Diethyl-3-hydroxytetradecylamine oxide 10 Sodium coconut oil soap 15 Sodium tallow soap 60 Triethanolammonium ethylenediaminetetraacetate 5 Moisture 10 Framed toilet bar Percent Dimethyl-2-hydroxydodecy1amine oxide 5 Sodium dodecylbenzenesulfonate 57 Glyceryl tristearate 38 Scouring cleanser Silica flour Detergent consisting of 85% trisodium phosphate and 15% dimethyl-3-hydroxyhexadecylamine oxide 15 To show the improvement in mildness of the compounds of this invention over trialkylamine oxides without a hydroxy group in the long chain R radical, dimethyldodecylamine oxide and dimethyl-Z-hydroxydodecylamine oxide were tested in accordance with the guinea pig immersion test. This test consists of immersing guinea pigs having shaved undersides up to their thorax in a 0.2% solution of the material being tested at 37 C., for a 4 /2 hour period per day for three consecutive days. The animals are graded three days after the last immersion. The grades are the average of the results on not less than three animals. A '1 to 10 scale is used to rate the efiects of the prolonged exposure of the test solution on the animals skin. Grade 10 represents ideal or perfect skin (soft, smooth and flexible) and the effect of a theoretically perfectly mild detergent compound; grade 1 represents severely irritated skin. Other values represent graduations of severity between these extremes. Grade 1 in the guinea pig immersion test indicates severely thickened, dry, cracked and bleeding skin, i.e., extreme irritation. (Grade 1 in exaggerated tests on human subjects would indicate severe redness and dryness of the skin. Exaggerated exposure tests on guinea pigs are much more extreme than those conducted on human subjects.) There is a good correlation between the results of the tests on guinea pigs and the results of normal use tests on humans; the guinea pig immersion test can be relied on to grade the relative mildness of detergent compounds toward the human skin. In guinea pig immersion tests dimethyldodecylamine oxide had a grade of 2, while dimethyl-Z-hydroxydodecylamine oxide has a grade of 5.
What is claimed is:
1. A detergent composition consisting essentially of from about 5% to about 80% of a tertiary amine oxide compound having the formula R R R N 0, wherein R is 2-hydroxyalkyl or 3-hydroxyalkyl in which the alkyl ranges in chain length from 10 to 18 carbon atoms and R and R are each methyl, ethyl, propyl or isopropyl and from about to about 20% of a material selected from the group consisting of water-soluble inorganic alkaline builder salts, water-soluble organic alkaline sequestrant builder salts, water-soluble soap, water-soluble synthetic organic non-soap anionic detergents and mixtures thereof.
2. The composition of claim 1 wherein the amine oxide is dimethyl-2-hydroxydodecylamine oxide.
3. The composition of claim 2 wherein the material is sodium tripolyphosphate.
4. The composition of claim 2 wherein the material is sodium dodecyl benzene sulfonate.
5. The composition of claim 1 wherein the amine oxide is dimet-hyl-3-hydroxydodecylamine oxide.
References Cited UNITED STATES PATENTS MAYER WEINBLA'IT, Primary Examiner.
U.S. C1. X.R.
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US726560A Expired - Lifetime US3441508A (en) | 1968-05-03 | 1968-05-03 | Detergent containing alkoxy hydroxypropylamine oxide |
US726609A Expired - Lifetime US3450637A (en) | 1968-05-03 | 1968-05-03 | Detergent containing hydroxy alkyl amine oxide |
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US726560A Expired - Lifetime US3441508A (en) | 1968-05-03 | 1968-05-03 | Detergent containing alkoxy hydroxypropylamine oxide |
Country Status (1)
Country | Link |
---|---|
US (2) | US3441508A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3609075A (en) * | 1968-06-25 | 1971-09-28 | Procter & Gamble | Cleaning and softening detergent compositions |
FR2132274A1 (en) * | 1971-04-02 | 1972-11-17 | Unilever Nv | |
US4275236A (en) * | 1979-12-26 | 1981-06-23 | Sherex Chemical Company, Inc. | Tertiary di-(β-hydroxy organo) amine oxides and their preparation |
US4325821A (en) * | 1979-08-15 | 1982-04-20 | Sherex Chemical Company, Inc. | Amine oxide promoters for froth flotation of mineral ores |
US4741863A (en) * | 1984-02-10 | 1988-05-03 | Toyota Jidosha Kabushiki Kaisha | Alkaline degreasing solution comprising amine oxides |
US20080098614A1 (en) * | 2006-10-03 | 2008-05-01 | Wyeth | Lyophilization methods and apparatuses |
JP2009024102A (en) * | 2007-07-20 | 2009-02-05 | Kao Corp | Liquid detergent composition |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4696771A (en) * | 1985-12-03 | 1987-09-29 | Henkel Corporation | Aminopolyols and polyurethanes prepared therefrom |
US5059625A (en) * | 1990-10-01 | 1991-10-22 | Olin Corporation | Polyglycidol amine oxide surfactants having antimicrobial activity |
GB9102311D0 (en) * | 1991-02-02 | 1991-03-20 | Albright & Wilson | Nitrosamine inhibition |
GB9202057D0 (en) * | 1992-01-31 | 1992-03-18 | Albright & Wilson | Synergistic inhibition of nitrosamines and nitrites |
JP4033896B2 (en) * | 1993-11-19 | 2008-01-16 | ザ、プロクター、エンド、ギャンブル、カンパニー | Detergent composition containing amine oxide and sulfate surfactant |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2169976A (en) * | 1934-01-26 | 1939-08-15 | Ig Farbenindustrie Ag | Process of producing assistants in the textile and related industries |
US3047579A (en) * | 1958-07-18 | 1962-07-31 | Shell Oil Co | Process for preparing n-oxides |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2999068A (en) * | 1959-04-27 | 1961-09-05 | Procter & Gamble | Personal use detergent lotion |
US3001945A (en) * | 1959-04-29 | 1961-09-26 | Procter & Gamble | Liquid detergent composition |
-
1968
- 1968-05-03 US US726560A patent/US3441508A/en not_active Expired - Lifetime
- 1968-05-03 US US726609A patent/US3450637A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2169976A (en) * | 1934-01-26 | 1939-08-15 | Ig Farbenindustrie Ag | Process of producing assistants in the textile and related industries |
US3047579A (en) * | 1958-07-18 | 1962-07-31 | Shell Oil Co | Process for preparing n-oxides |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3609075A (en) * | 1968-06-25 | 1971-09-28 | Procter & Gamble | Cleaning and softening detergent compositions |
FR2132274A1 (en) * | 1971-04-02 | 1972-11-17 | Unilever Nv | |
US4325821A (en) * | 1979-08-15 | 1982-04-20 | Sherex Chemical Company, Inc. | Amine oxide promoters for froth flotation of mineral ores |
US4275236A (en) * | 1979-12-26 | 1981-06-23 | Sherex Chemical Company, Inc. | Tertiary di-(β-hydroxy organo) amine oxides and their preparation |
WO1981001847A1 (en) * | 1979-12-26 | 1981-07-09 | Sherex Chem | Tertiary di-(beta-hydroxy organo)amine oxides and their preparation |
US4741863A (en) * | 1984-02-10 | 1988-05-03 | Toyota Jidosha Kabushiki Kaisha | Alkaline degreasing solution comprising amine oxides |
US20080098614A1 (en) * | 2006-10-03 | 2008-05-01 | Wyeth | Lyophilization methods and apparatuses |
JP2009024102A (en) * | 2007-07-20 | 2009-02-05 | Kao Corp | Liquid detergent composition |
Also Published As
Publication number | Publication date |
---|---|
US3441508A (en) | 1969-04-29 |
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