WO1998055580A1 - Process for making solid amine oxide surfactant composition - Google Patents
Process for making solid amine oxide surfactant composition Download PDFInfo
- Publication number
- WO1998055580A1 WO1998055580A1 PCT/US1997/009510 US9709510W WO9855580A1 WO 1998055580 A1 WO1998055580 A1 WO 1998055580A1 US 9709510 W US9709510 W US 9709510W WO 9855580 A1 WO9855580 A1 WO 9855580A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- amine oxide
- complexing
- carbon atoms
- groups
- Prior art date
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- 150000001412 amines Chemical class 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 239000007787 solid Substances 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims description 45
- 239000004094 surface-active agent Substances 0.000 title claims description 34
- 239000002253 acid Substances 0.000 claims abstract description 53
- 230000000536 complexating effect Effects 0.000 claims abstract description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 33
- 239000002244 precipitate Substances 0.000 claims description 21
- 235000019832 sodium triphosphate Nutrition 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 229920002125 Sokalan® Polymers 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004584 polyacrylic acid Substances 0.000 claims description 5
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 claims description 5
- 235000019818 tetrasodium diphosphate Nutrition 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 229940120146 EDTMP Drugs 0.000 claims description 2
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 claims description 2
- 239000005639 Lauric acid Substances 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960004585 etidronic acid Drugs 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 abstract description 6
- 239000003599 detergent Substances 0.000 abstract description 6
- 239000008247 solid mixture Substances 0.000 abstract description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 3
- 239000002453 shampoo Substances 0.000 abstract description 3
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 8
- 150000003512 tertiary amines Chemical class 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- -1 dodecylmethylethyl amine Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ONHFWHCMZAJCFB-UHFFFAOYSA-N myristamine oxide Chemical compound CCCCCCCCCCCCCC[N+](C)(C)[O-] ONHFWHCMZAJCFB-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000007605 air drying Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IBOBFGGLRNWLIL-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine oxide Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)[O-] IBOBFGGLRNWLIL-UHFFFAOYSA-N 0.000 description 2
- UTTVXKGNTWZECK-UHFFFAOYSA-N n,n-dimethyloctadecan-1-amine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)[O-] UTTVXKGNTWZECK-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000949473 Correa Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- YXVFQADLFFNVDS-UHFFFAOYSA-N diammonium citrate Chemical compound [NH4+].[NH4+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O YXVFQADLFFNVDS-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000007602 hot air drying Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IOKYPACLTOWHCM-UHFFFAOYSA-N n,n-diethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(CC)CC IOKYPACLTOWHCM-UHFFFAOYSA-N 0.000 description 1
- ADXNPXDFKKWVGE-UHFFFAOYSA-N n,n-dimethyltridecan-1-amine Chemical compound CCCCCCCCCCCCCN(C)C ADXNPXDFKKWVGE-UHFFFAOYSA-N 0.000 description 1
- SKRQXOLEJYUCIG-UHFFFAOYSA-N n,n-dipropylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(CCC)CCC SKRQXOLEJYUCIG-UHFFFAOYSA-N 0.000 description 1
- FLZHCODKZSZHHW-UHFFFAOYSA-N n,n-dipropyltetradecan-1-amine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])(CCC)CCC FLZHCODKZSZHHW-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
- 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0082—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads
-
- 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
-
- 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2079—Monocarboxylic acids-salts thereof
-
- 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2082—Polycarboxylic acids-salts thereof
-
- 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2086—Hydroxy carboxylic acids-salts thereof
-
- 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
- C11D3/36—Organic compounds containing phosphorus
- C11D3/361—Phosphonates, phosphinates or phosphonites
-
- 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
- C11D3/36—Organic compounds containing phosphorus
- C11D3/364—Organic compounds containing phosphorus containing nitrogen
-
- 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
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
- C11D3/3761—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions in solid compositions
Definitions
- the present invention relates to a process for preparing solid compositions containing amine oxide-acid salts.
- Such compositions are a source of solid, concentrated amine oxide surfactants for incorporation into cleaning products, especially solid or granular cleaning products.
- Amine oxides are commonly used in cleaning compositions to boost and maintain suds formation.
- Such compositions include, for example, laundry, shampoo and dish washing detergent compositions.
- amine oxide surfactants from the corresponding tertiary amine are known. Such methods involve the conversion of a tertiary amine in the presence of a strong oxidizing agent to the corresponding amine oxide. For example, tertiary amines can be reacted with hydrogen peroxide to yield a 30-40% aqueous solution of the corresponding amine oxide. Catalysts are commonly used to facilitate the reaction. Most of these methods, however, result in liquid formulations containing the amine oxide.
- solid amine oxide surfactant formulations are desirable than typical amine oxide surfactant formulations that are commercially available, such as in liquid, gel, or paste form.
- amine oxide surfactants have been many attempts at preparing amine oxide surfactants in solid or granular formulations.
- U.S. 5,399,296, granted on March 21, 1995 to Wierenga et al. and U.S. 5,389,306 granted on February 14, 1995 to Wierenga et al. disclose solid amine oxide compositions containing amine oxide-maleic acid salts and the process for making such compositions.
- the foregoing considerations involving amine oxide surfactant formulations and the processes for preparing them indicate that there is a continuing need to provide solid formulations containing amine oxide surfactants. None of the existing art provides all of the advantages and benefits of the present invention.
- solid amine oxide compositions containing amine oxide-maleic acid salts can be formed.
- Such other solid amine oxide surfactant compositions can be used as a source of amine oxide surfactants in cleaning compositions.
- the present invention is directed to a process for preparing solid amine oxide surfactant compositions which are useful in formulating detergent products, such as laundry detergents, shampoos, personal cleansing compositions, and cosmetic compositions, especially solid or granular cleaning products.
- the process comprises admixing the complexing acid with an amine oxide surfactant formulation by admixing 1 mole of complexing acid with X mole(s) of amine oxide, where X is from about 1 to about equal to the number of acid groups of the complexing acid.
- the pH of the admixture is from about 1 to about 3, whereby a visible precipitate in the admixture is formed.
- the formed precipitate is separated from the admixture, preferably by mechanical means, and allowed to dry.
- the separated precipitate forms the solid compositions of the present invention, which solid compositions consist of the amine oxide and complexing acid described above.
- solid compositions mean particulate (e.g. powders, granules, agglomerates) and non-particulate solids. As used herein, all pKa and pH values are measured in water at 25°C.
- Amine oxide formulations for use in the process herein comprise varying amounts of amine oxide surfactant therein.
- Such amine oxide formulations, and the processes for preparing them, are well known in the surfactant art.
- the amine oxide formulations for use in the instant process comprise varying percentages of amine oxide surfactant.
- Amine oxide surfactants are commercially available in many physical forms, including liquid, paste, gel and solid.
- the percentage of amine oxide surfactant in the formulation, as well as the type of such amine oxide surfactant, are not critical to the successful operation of the instant process. Accordingly, any known or conventional amine oxide formulation can be used.
- Such known or conventional formulations typically contain from about 3% to about 80%, more typically from about 5% to about 20%, most preferably from about 5% to about 10% by weight of amine oxide surfactant in a dilute water solution. It is understood, however, that formulations containing higher and lower concentrations of amine oxide surfactant can also be used in the instant process.
- Amine oxide surfactants for use in the instant process preferably have the formula RR'R"NO, where R is a substituted or unsubstituted alkyl or alkenyl group containing from about 6 to about 30, preferably about 8 to 18 carbon atoms.
- Groups R' and R" are each substituted or unsubstituted alkyl or alkenyl groups containing from about 1 to about 18, preferably from about 1 to about 4, carbon atoms.
- R' and R" are each methyl groups, examples of which include dodecyldimethyl amine oxide, tetradecyldimethyl amine oxide, hexadecyldimethyl amine oxide, octadecyldimethyl amine oxide, and coconutalkyldimethylamine oxides.
- Suitable amine oxide surfactants for use in the instant process include, but are not limited to, dodecyldimethyl amine oxide, tridecyldimethyl amine oxide, tetradecyldi-methyl amine oxide, pentadecyldimethyl amine oxide, hexadecyldimethyl amine oxide, heptadecyldimethyl amine oxide, octadecyldimethyl amine oxide, dodecyldiethyl amine oxide, tetradecyldimethyl amine oxide, hexadecyldiethyl amine oxide, octadecyldiethyl amine oxide, dodecyldipropyl amine oxide, tetradecyldipropyl amine oxide, hexadecyldipropyl amine oxide, octadecyldipropyl amine oxide, dodecyldibut
- ADMOXTM is a C14 amine oxide dihydrate.
- ADMOXTM and other amine oxides useful in the present process are set forth in U.S. Patent No. 5,292,955 (Smith and Sauer, issued March 8, 1994).
- amine oxide surfactants made by the oxidation of tertiary amines prepared from mixed alcohols obtainable from coconut oil. Such coconutalkyl amine oxides are preferred from an economic standpoint inasmuch as it is not necessary for the present purposes, to separate the mixed alcohol fractions into their pure components to secure the pure chain length fractions of the amine oxides.
- Amine oxide formulations for use in the present process can be prepared by known and conventional methods. Such methods normally involve the controlled oxidation of tertiary amines to the corresponding amine oxide using a strong oxidizing agent.
- a preferred oxidizing agent is hydrogen peroxide.
- a dilute, or preferably concentrated (30% by weight of more), hydrogen peroxide solution is added in a stoichiometric or greater amount to a liquid solution containing the tertiary amine for conversion thereof to the amine oxide.
- Reaction rates and amine oxide yields can be improved by incorporation of catalysts and or chelating agents well known in the surfactant art for this particular application. Methods for making amine oxide surfactants are described, for example, in U.S.
- Patent 3,215,741 Chadwick, issued November 2, 1965
- U.S. Patent 3,223,647 Drew and Voss, issued December 14, 1965
- British Patent 437,566 issued October 31, 1935
- U.S. Patent 4,565,891 Correa and Riley, issued July 19, 1984.
- the process for preparing the solid compositions of the present invention involved admixing a complexing acid with the amine oxide formulation described herein before.
- Complexing acid is defined as a saturated carboxylic acid with at least 5 carbon atoms, unsaturated carboxylic acid with at least 5 carbon atoms, phosphonic acid, and mixtures thereof.
- Such complexing acids will effectively precipitate amine oxide surfactants from the amine oxide formulations.
- carboxylates means carboxyl-containing compounds generally.
- the complexing acids of the present invention can be in a powdery form, or in an aqueous solution, although the physical form of the complexing acid is not critical to the invention.
- the complexing acid is soluble in water at less than about 35°C.
- E ⁇ xamples of saturated and unsaturated carboxylic acids with at least 5 carbon atoms includes citric acid, polyacrylic acid, malonic acid, adipic acid, oxalic acid, glutaric acid, pthalic acid, lauric acid, oleic acid, benzoic acid, and butyric acid.
- phosphonic acids examples include tetra sodium pyrophosphate (TSPP), sodium tripolyphosphate (STPP), diethylene triamine penta methyl phosphonic acid, hydroxyethane diphosphonic acid, and ethylenediamine tetra methylene phosphonic acid.
- TSPP tetra sodium pyrophosphate
- STPP sodium tripolyphosphate
- diethylene triamine penta methyl phosphonic acid hydroxyethane diphosphonic acid
- hydroxyethane diphosphonic acid hydroxyethane diphosphonic acid
- ethylenediamine tetra methylene phosphonic acid examples include ethylenediamine tetra methylene phosphonic acid.
- Preferred polyacrylic acids have a molecular weight range of from about 2,500 to 70,000, preferably a molecular weight range of from about 10,000 to about 50,000.
- Water soluble salts of the complexing acid can also be used in the instant process.
- Such salts can comprise alkali metals (e.g., sodium, potassium), alkali earth metals, ammonium, substituted ammonium, and so forth.
- alkali metals e.g., sodium, potassium
- alkali earth metals e.g., sodium, potassium
- ammonium substituted ammonium
- Preferred among such salts are sodium citrate, diammonium citrate, sodium tripolyphosphate and sodium pyrophosphate.
- Other water soluble salts can be used in the instant process provided that such salts are compatible with the amine oxide surfactant selected for use herein.
- An essential step in the instant process is adding the complexing acid in the requisite amounts to the amine oxide formulation to form a solid amine oxide surfactant composition. It is preferred that the amine oxide be diluted in a water solution, having an active level of from about 3% to about 80%, preferably from about 5% to about 20%, most preferably from about 5% to about 10%. pH adjustment of the amine oxide formulation to the requisite level to about 1 to about 3 is normally needed when the complexing acid is used in the instant process. Precipitation of the desired amine oxide salt will not occur to any large extent until such admixture pH values are realized.
- the complex is formed by admixing 1 mole of complexing acid with X mole(s) of amine oxide, where X is from about 1 to about equal to the number of acid groups of the complexing acid. X should be within about plus or minus 25%, preferably about plus or minus 10%, of the number of acid groups in the complexing acid.
- the pH of the admixture is from about 1 to about 3, whereby a visible precipitate in the admixture is formed. The formed precipitate is separated from the admixture, preferably by mechanical means, and allowed to dry.
- the process of the present invention is described herein in terms of the addition of the complexing acid to an amine oxide formulation. It is understood, however, that any reference herein to complexing acid implicitly includes salts of complexing acids (described herein before), complexing acids which are acids, and mixtures thereof. Process
- the process of the present invention comprises admixing the complexing acid and an amine oxide formulation to form a visible precipitate therein, and then separating the formed precipitate from the admixture.
- the process is described in detail as follows.
- one mole of a complexing acid and X moles of an amine oxide formulation described herein (10% active in a dilute solution of water) are admixed, wherein X is from about 1 to about equal to the number of acid groups of the complexing acid.
- the pH of the admixture is from about 1 to about 3, whereby a visible precipitate in the admixture is formed.
- the formed precipitate made in accordance with the instant process is a salt of the amine oxide surfactant and complexing acid.
- an excess of complexing acid is used to accelerate the formation of the precipitate.
- An excess of about 30% complexing acid above the molar amount described above is preferred.
- the formed precipitate is separated from the admixture.
- separation is accomplished by mechanical means such as screening, filtering, centrifuging and the like.
- the separated precipitate can then be washed with cold water (pH adjusted to about the pKa of the amine oxide) to remove unprecipitated reactants, and then dried to form a solid formulation.
- the solid formulation can be reduced to fine particles, agglomerated, and so forth. Since the precipitate can be separated by mechanical means, there is no need to use organic extraction solvents to perform such separations.
- citric acid complexing acid is admixed with about 30 grams of amine oxide solution (C14 alkyldimethyl amine oxide, 10% active in a solution of water).
- the molar ratio of complexing acid to active amine oxide is about 1 :2.
- the pH of the admixture of amine oxide solution and citric acid is from about 1 to about 3. pH is adjusted with the addition of excess citric acid. A visible precipitate forms almost immediately.
- the admixture is allowed to set for about 5 minutes.
- the precipitate is then filtered from the admixture, washed with water (pH of 7), in which the water has substantially all the impurities removed, and air dried before it is reduced to a fine powder.
- the citric acid is preferably in a powder form.
- Example 2 The process described in Example 1 is repeated, except that 30 grams of C16 alkyldimethyl amine oxide (7.85% solution) is admixed with a solution of 0.76 grams of citric acid, thereby forming a precipitate. After adding the initial citric acid and after the precipitate is formed, an additional 0.40 grams of citric acid is added to adjust the viscosity. The molar ratio of complexing acid to active amine oxide is 1:1.5.
- Example 2 The process described in Example 1 is repeated, except that 5.27 grams of C16 alkyldimethyl amine oxide (6.4% solution) is admixed with a solution of
- citric acid 0.09 grams of citric acid.
- the molar ratio of complexing acid to active amine oxide is 1:3, and the pH of C16 alkyldimethyl amine oxide solution is adjusted using 1 N HCI to a pH of 0.97, before the addition of the citric acid.
- Example 4 The process described in Example 1 is repeated except that 365 grams of
- C14 alkyldimethyl amine oxide (10% solution) is admixed with 4.31 grams of diethylene triamine penta methyl phosphonic acid (25% active).
- the molar ratio of complexing acid to active amine oxide is 1:5, and the pH is adjusted using 1N HCI to a pH of 1.0 before the addition of the complexing acid.
- Example 6 The process described in E ⁇ xample 1 is repeated except that 47 grams of C14 alkyldimethyl amine oxide (9.8% solution) is admixed with 9.35 grams of polyacrylic acid (molecular weight 4,500) complexing acid (48% active). The molar ratio of complexing acid to active amine oxide is 1 :24. No pH adjustment is necessary before the addition of the polyacrylic acid.
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002293527A CA2293527A1 (en) | 1997-06-03 | 1997-06-03 | Process for making solid amine oxide surfactant composition |
BR9714728-1A BR9714728A (en) | 1997-06-03 | 1997-06-03 | Process for producing solid amine oxide surfactant composition |
PCT/US1997/009510 WO1998055580A1 (en) | 1997-06-03 | 1997-06-03 | Process for making solid amine oxide surfactant composition |
EP97926875A EP0988368A1 (en) | 1997-06-03 | 1997-06-03 | Process for making solid amine oxide surfactant composition |
AU31534/97A AU3153497A (en) | 1997-06-03 | 1997-06-03 | Process for making solid amine oxide surfactant composition |
ARP980102577A AR015846A1 (en) | 1997-06-03 | 1998-06-02 | PROCESS FOR PREPARING SOLID COMPOUNDS OF AMINA OXIDE TENSOACTIVE. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1997/009510 WO1998055580A1 (en) | 1997-06-03 | 1997-06-03 | Process for making solid amine oxide surfactant composition |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998055580A1 true WO1998055580A1 (en) | 1998-12-10 |
Family
ID=22261008
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US1997/009510 WO1998055580A1 (en) | 1997-06-03 | 1997-06-03 | Process for making solid amine oxide surfactant composition |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0988368A1 (en) |
AR (1) | AR015846A1 (en) |
AU (1) | AU3153497A (en) |
CA (1) | CA2293527A1 (en) |
WO (1) | WO1998055580A1 (en) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3341459A (en) * | 1964-05-25 | 1967-09-12 | Procter & Gamble | Detergent compositions |
EP0060711A1 (en) * | 1981-03-17 | 1982-09-22 | THE PROCTER & GAMBLE COMPANY | Solid detergent compositions containing alpha-amine oxide surfactants |
EP0421327A1 (en) * | 1989-10-02 | 1991-04-10 | Albemarle Corporation | Heavy duty laundry detergent |
US5292955A (en) * | 1991-07-26 | 1994-03-08 | Ethyl Corporation | Amine oxide complexes |
US5389306A (en) * | 1994-04-22 | 1995-02-14 | The Procter & Gamble Company | Process for making solid formulations containing amine oxide surfactants |
US5399296A (en) * | 1994-04-22 | 1995-03-21 | The Procter & Gamble Company | Solid compositions containing amine oxide-maleic acid salts |
-
1997
- 1997-06-03 AU AU31534/97A patent/AU3153497A/en not_active Abandoned
- 1997-06-03 EP EP97926875A patent/EP0988368A1/en not_active Withdrawn
- 1997-06-03 CA CA002293527A patent/CA2293527A1/en not_active Abandoned
- 1997-06-03 WO PCT/US1997/009510 patent/WO1998055580A1/en not_active Application Discontinuation
-
1998
- 1998-06-02 AR ARP980102577A patent/AR015846A1/en unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3341459A (en) * | 1964-05-25 | 1967-09-12 | Procter & Gamble | Detergent compositions |
EP0060711A1 (en) * | 1981-03-17 | 1982-09-22 | THE PROCTER & GAMBLE COMPANY | Solid detergent compositions containing alpha-amine oxide surfactants |
EP0421327A1 (en) * | 1989-10-02 | 1991-04-10 | Albemarle Corporation | Heavy duty laundry detergent |
US5292955A (en) * | 1991-07-26 | 1994-03-08 | Ethyl Corporation | Amine oxide complexes |
US5389306A (en) * | 1994-04-22 | 1995-02-14 | The Procter & Gamble Company | Process for making solid formulations containing amine oxide surfactants |
US5399296A (en) * | 1994-04-22 | 1995-03-21 | The Procter & Gamble Company | Solid compositions containing amine oxide-maleic acid salts |
Also Published As
Publication number | Publication date |
---|---|
AR015846A1 (en) | 2001-05-30 |
EP0988368A1 (en) | 2000-03-29 |
AU3153497A (en) | 1998-12-21 |
CA2293527A1 (en) | 1998-12-10 |
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