US3441508A - Detergent containing alkoxy hydroxypropylamine oxide - Google Patents
Detergent containing alkoxy hydroxypropylamine oxide Download PDFInfo
- Publication number
- US3441508A US3441508A US726560A US3441508DA US3441508A US 3441508 A US3441508 A US 3441508A US 726560 A US726560 A US 726560A US 3441508D A US3441508D A US 3441508DA US 3441508 A US3441508 A US 3441508A
- Authority
- US
- United States
- Prior art keywords
- sodium
- detergents
- amine oxides
- oxide
- alkoxy
- 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
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- 239000003599 detergent Substances 0.000 title description 37
- -1 alkoxy hydroxypropylamine oxide Chemical compound 0.000 title description 15
- 239000000203 mixture Substances 0.000 description 28
- 150000003839 salts Chemical class 0.000 description 16
- 150000003512 tertiary amines Chemical class 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 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 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- 239000000344 soap Substances 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
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000003352 sequestering agent Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 235000019832 sodium triphosphate Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007859 condensation product 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 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
- 239000007788 liquid Substances 0.000 description 2
- 229920005646 polycarboxylate Polymers 0.000 description 2
- 239000001205 polyphosphate Substances 0.000 description 2
- 235000011176 polyphosphates Nutrition 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- QEVPNCHYTKOQMP-UHFFFAOYSA-N 3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1 QEVPNCHYTKOQMP-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
- 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-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
- 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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 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
- 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
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000003085 diluting agent Substances 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
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 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
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 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
- 239000002304 perfume Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 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
- 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
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 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
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940083982 sodium phytate Drugs 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
- 235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
- 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 238000005494 tarnishing Methods 0.000 description 1
- JZBRFIUYUGTUGG-UHFFFAOYSA-J tetrapotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [K+].[K+].[K+].[K+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O JZBRFIUYUGTUGG-UHFFFAOYSA-J 0.000 description 1
- 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
- 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
- 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
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 3-alkoxy-2-hydroxypropyl in which the alkoxy, ranges from to 18 carbon atoms in chain length; R and R are each methyl, ethyl, propyl or isopropyl.
- R R N O The class of compounds described above will hereinafter be referred to more simply as R R R N O.
- Examples of the compounds of this invention are: N, N dimethyl 3 dodecoxy 2 hydroxypropylamine oxide; N,N diethyl 3 tetradecoxy 2 hydroxypropyl amine.
- 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 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 described above. If the 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. Likewise, if R and R contain more than 3 carbon atoms, desired detergency characteristics are not obtained.
- the long chain 3-alkoxy-2-hydroxypropyl R radical must contain a hydroxy group in the 2 position (i.e., the second carbon atom from the nitrogen) in order to achieve improved rnildness, hygroscopicity and thermostability characteristics in accordance with this invention.
- the 3-alkoxy-2-hydroxypropyl R radical has the following general formula wherein R ranges from 10 to 18 carbon atoms in chain length.
- the 3-alkoxy-2-hydroxypropyl compounds have reduced hygroscopicity characteristics as compared to the corresponding compound containing unsubstituted R alkyl 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 alkoxy in R varies in chain length in the C to C range, as for example, the alkoxy groups derived from coconut fatty alcohol (or distilled coconut fatty alcohol). Those amine oxides in which the 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 corresponding tertiary amine. See, for example, British Patent 437,566.
- the corresponding tertiary amine in general, can be prepared, 'by reacting an appropriate long chain alkyl compound with the appropriate secondary amine.
- the examples explain in detail such reactions.
- the preparation of alkyl glycidyl ethers (a source of the 3-alkoxy-2-hydroxypropyl 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, flakes, 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 of the tertiary amine oxides of this invention and from about 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 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 used 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 detergents used alone or in admixture include both the soap and on-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 polyethenoxy 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 alkyolammonium salts, for example.
- Specific examples are: sodium lauryl sulfate; potassium N-methyl lauroyl tauride; triethanolammonium dodecylbenzenesulfonate.
- nonionic organic detergents are: polyethylene oxide condensates of alkyl phenols wherein the alkyl group contains from 6 to 12 carbon atoms (e.g., 5- octylphenol) and the ethylene oxide is present in a molar ratio of ethylene oxide to alkyl phenol in the range of 10:1 to :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 product of from about 5 to 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).
- Water-soluble inorganic alkaline builder salts used alone or in admixture 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, sodium bicarbonate, potassium tripolyphosphate, potassium pyrophosphate, sodium hexametaphosphate, sodium sesquicarbonate, sodium monoand di-ortho phosphate and potassium bicarbonate. Such inorganic builder salts enhance the detergency of the subject amine oxides.
- water-soluble organic alkaline sequestrant builder salts used alone or in admixture are alkali metal, ammonium 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.
- alkali metal, ammonium 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-diaminocycylhexanetetraacetates.
- 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 alkoxy R contains 12 to 14 carbon atoms are used in such preferred compositions.
- 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.
- 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-Z-hydroxy-propyl amine and N,N-dimethyl(-3-hexadecoxy-2-hydroxypr0pylamine oxide can be prepared by processes similar to that described.
- the tertiary amine oxides of this invention can be used in effective detergent compositions having improved hygroscopicity and thermal stability characteristics.
- composition of claim 1 wherein the amine ox- References Clted ide is N,N-dimethyl-3-dodecoxy-Z-hydroxypropylamine UNITED STATES PATENTS 5 2,999,068 9/1961 Pilcher et al. 202-137 3.
- the composition of claim 2 wherein the said ma- 3,001,945 9/1961 Drew et terial is sodium dodecyl-benzene sulfonate.
- composition of claim 2 wherein the said ma- 252-152; 260-584
Description
United States Patent US. Cl. 252137 5 Claims ABSTRACT OF THE DISCLOSURE A-lkoxy hydroxypropyl amine oxides having improved hygoscopicity and thermal stability properties are employed in detergent compositions containing alkaline builders or other synthetic detergents.
CROSS REFERENCE This is a division of copending applications Ser. No. 156,993, filed Dec. 4, 1961 and 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.
The amine oxides of this invention are:
In the above formula R is 3-alkoxy-2-hydroxypropyl in which the alkoxy, ranges from to 18 carbon atoms in chain length; R and R are each methyl, ethyl, propyl or isopropyl. The class of compounds described above will hereinafter be referred to more simply as R R R N O.
Examples of the compounds of this invention are: N, N dimethyl 3 dodecoxy 2 hydroxypropylamine oxide; N,N diethyl 3 tetradecoxy 2 hydroxypropyl amine.
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 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 described above. If the 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. Likewise, if R and R contain more than 3 carbon atoms, desired detergency characteristics are not obtained. The long chain 3-alkoxy-2-hydroxypropyl R radical must contain a hydroxy group in the 2 position (i.e., the second carbon atom from the nitrogen) in order to achieve improved rnildness, 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-2-hydroxypropyl R radical has the following general formula wherein R ranges from 10 to 18 carbon atoms in chain length.
The 3-alkoxy-2-hydroxypropyl compounds have reduced hygroscopicity characteristics as compared to the corresponding compound containing unsubstituted R alkyl 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 alkoxy in R varies in chain length in the C to C range, as for example, the alkoxy groups derived from coconut fatty alcohol (or distilled coconut fatty alcohol). Those amine oxides in which the 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 corresponding tertiary amine. See, for example, British Patent 437,566. The corresponding tertiary amine, in general, can be prepared, 'by reacting an appropriate long chain alkyl compound with the appropriate secondary amine. The examples explain in detail such reactions. The preparation of alkyl glycidyl ethers (a source of the 3-alkoxy-2-hydroxypropyl 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, flakes, 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 of the tertiary amine oxides of this invention and from about 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 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 used 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 detergents used alone or in admixture include both the soap and on-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 polyethenoxy 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 alkyolammonium salts, for example. Specific examples are: sodium lauryl sulfate; potassium N-methyl lauroyl tauride; triethanolammonium dodecylbenzenesulfonate.
The examples of nonionic organic detergents are: polyethylene oxide condensates of alkyl phenols wherein the alkyl group contains from 6 to 12 carbon atoms (e.g., 5- octylphenol) and the ethylene oxide is present in a molar ratio of ethylene oxide to alkyl phenol in the range of 10:1 to :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 product of from about 5 to 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).
Water-soluble inorganic alkaline builder salts used alone or in admixture 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, sodium bicarbonate, potassium tripolyphosphate, potassium pyrophosphate, sodium hexametaphosphate, sodium sesquicarbonate, sodium monoand di-ortho phosphate and potassium bicarbonate. Such inorganic builder salts enhance the detergency of the subject amine oxides.
Examples of water-soluble organic alkaline sequestrant builder salts used alone or in admixture are alkali metal, ammonium 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 these polycarboxylates are also suitable. Other organic alkaline sequestrant builder salts which can be used are: Hydroxyethylethylenediaminetriacetates; 2 hydroxyethyliminodiacetates; diethylenetriaminepentaacetates; 1,2-diaminocycylhexanetetraacetates. 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 alkoxy R contains 12 to 14 carbon atoms are used in such preferred compositions.
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 is an example which illustrates the tertiary amine oxide compositions of this invention.
EXAMPLE 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 F. A pressure of 450 p.s.i. was obtained in the autoclave by charging dimethyl amine into the autoclave using nitrogen pressure. A dimethyl amine blead 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-Z-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:
1,000 grams of this tertiary amine was mixed with 2,789.3 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-Z-hydroxy-propyl amine and N,N-dimethyl(-3-hexadecoxy-2-hydroxypr0pylamine oxide can be prepared by processes similar to that described.
The tertiary amine oxides of this invention can be used in effective detergent compositions having improved hygroscopicity and thermal stability characteristics. One has the following formula:
Spray-dried granular detergent Percent N,N-dimethyl-3-dodecoxy-2-hydroxypropylamine oxide 5 Sodium dodecylbenzenesulfonate 15 Sodium tripolyphosphate 50 Sodium sulfate 15 Sodium silicate 5 Moisture 10 5 6 tergents, inorganic alkaline builder salts, organic alkaterial is a mixture of sodium dodecylbenzene sulfonate line sequestrant builder salts and mixtures thereof. and Sodium tripolyphosphate- 2. The composition of claim 1 wherein the amine ox- References Clted ide is N,N-dimethyl-3-dodecoxy-Z-hydroxypropylamine UNITED STATES PATENTS 5 2,999,068 9/1961 Pilcher et al. 202-137 3. The composition of claim 2 wherein the said ma- 3,001,945 9/1961 Drew et terial is sodium dodecyl-benzene sulfonate.
4. The composition of claim 2 wherein the said ma- MAYER W T, Prima y xa n terial is sodium tn'polyphosphate. 10 U5, C1, X R
5. The composition of claim 2 wherein the said ma- 252-152; 260-584
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US72660968A | 1968-05-03 | 1968-05-03 | |
US72656068A | 1968-05-03 | 1968-05-03 |
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US3441508A true US3441508A (en) | 1969-04-29 |
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ID=27111344
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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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US726609A Expired - Lifetime US3450637A (en) | 1968-05-03 | 1968-05-03 | Detergent containing hydroxy alkyl amine oxide |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2132274A1 (en) * | 1971-04-02 | 1972-11-17 | Unilever Nv | |
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 |
US5223644A (en) * | 1991-02-02 | 1993-06-29 | Albright & Wilson Limited | Nitrosamine inhibition |
US5442113A (en) * | 1992-01-31 | 1995-08-15 | Albright & Wilson Limited | Nitrosamine and nitrite inhibition |
US5478500A (en) * | 1993-11-19 | 1995-12-26 | The Procter & Gamble Company | Detergent composition containing optimum levels of amine oxide and linear alkylbenzene sulfonate surfactants for improved solubility in cold temperature laundering solutions |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3609075A (en) * | 1968-06-25 | 1971-09-28 | Procter & Gamble | Cleaning and softening detergent compositions |
WO1981000527A1 (en) * | 1979-08-15 | 1981-03-05 | Sherex Chem | 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 |
JPS60169583A (en) * | 1984-02-10 | 1985-09-03 | Toyota Motor Corp | Alkali degreasing solution and alkali degreasing agent |
RU2009111140A (en) * | 2006-10-03 | 2010-11-10 | Вайет (Us) | DEVICES AND METHODS OF LYOFILIZATION |
JP5238197B2 (en) * | 2007-07-20 | 2013-07-17 | 花王株式会社 | Liquid detergent composition |
Citations (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 |
Family Cites Families (2)
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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 |
-
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 |
---|---|---|---|---|
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 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2132274A1 (en) * | 1971-04-02 | 1972-11-17 | Unilever Nv | |
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 |
US5223644A (en) * | 1991-02-02 | 1993-06-29 | Albright & Wilson Limited | Nitrosamine inhibition |
US5442113A (en) * | 1992-01-31 | 1995-08-15 | Albright & Wilson Limited | Nitrosamine and nitrite inhibition |
US5478500A (en) * | 1993-11-19 | 1995-12-26 | The Procter & Gamble Company | Detergent composition containing optimum levels of amine oxide and linear alkylbenzene sulfonate surfactants for improved solubility in cold temperature laundering solutions |
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