US3626034A - Dialkyl phosphoryl n-alkyltaurinates - Google Patents
Dialkyl phosphoryl n-alkyltaurinates Download PDFInfo
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- US3626034A US3626034A US686747A US3626034DA US3626034A US 3626034 A US3626034 A US 3626034A US 686747 A US686747 A US 686747A US 3626034D A US3626034D A US 3626034DA US 3626034 A US3626034 A US 3626034A
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- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 16
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 11
- 238000005108 dry cleaning Methods 0.000 abstract description 7
- 239000011591 potassium Substances 0.000 abstract description 6
- 229910052700 potassium Inorganic materials 0.000 abstract description 6
- 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 abstract description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 5
- 239000011734 sodium Substances 0.000 abstract description 5
- 229910052708 sodium Inorganic materials 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 19
- 239000003599 detergent Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000002689 soil Substances 0.000 description 13
- -1 amine alkyl aryl sulfonate Chemical class 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- IEGMHVAFJPVOFY-UHFFFAOYSA-N 1-[chloro(octoxy)phosphoryl]oxyoctane Chemical compound CCCCCCCCOP(Cl)(=O)OCCCCCCCC IEGMHVAFJPVOFY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 241000272534 Struthio camelus Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 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
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- GWLWWNLFFNJPDP-UHFFFAOYSA-M sodium;2-aminoethanesulfonate Chemical compound [Na+].NCCS([O-])(=O)=O GWLWWNLFFNJPDP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
- D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- 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
- C11D1/02—Anionic compounds
- C11D1/34—Derivatives of acids of phosphorus
- C11D1/347—Other P-containing anionic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/886—Ampholytes containing P
Definitions
- R is an alkyl group containing from six to 16 carbon atoms
- R is an alkyl group containing from six to 16 carbon atoms
- R can be hydrogen, an alkyl group containing from one to eight carbon atoms or an aryl group containing from one to eight carbon atoms
- Y is selected from the group consisting of sodium, potassium, ammonium and mixtures thereof, and n is an integer from one to four.
- R can be an alkyl group containing from six to 16 carbon atoms; R can be an alkyl group containing from six to 16 carbon atoms; R can be hydrogen, an alkyl group containing from one to eight carbon atoms or an aryl group containing from one to eight carbon atoms and Y can be sodium, potassi um or ammonium and n can be an integer from one to four. It has been found that the above compound is provided with all the properties that are required of detergents employed in the common solvent systems as above noted.
- the amount of materials of the present invention that can be employed with the solvent system may range between 0. l0 to 10.0 percent by weight.
- the dialkyl phosphoryl N-alkyl taurinates are formulated by first reacting phosphorus trichloride with an alkyl alcohol to form a dialkyl phosphite.
- the alcohols that may be used may be methanol, ethanol, propanol, isopropanol, butanol, and isobutanol.
- the dialkyl phosphite may be reacted with another alcohol containingfrom six to 16 carbon atoms to produce transesteritication to the higher molecular weight phosphite. ester.
- the reaction product is then chlorinated to produce the corresponding dialkyl phosphorochloridate.
- Thelatter intermediate is then reacted with sodium or potassium N-alkyl taurinate or a homolo gthereof, in a manner well known in the art, producing the final product in high yield.
- EXAMPLE 1 A 500 g. solution of 65 percent N-me'thyl sodium taurinate (46 percent excess over 2 mole proportions) was treated at 20 C., with octyl decylphosphorochloridate and toluene by adding the same over a period of L5 hours and then stirring the same at 25 C., for 2 additional hours. The solids and aqueous byproducts were separated by centrifuging. Thereafter, the solution phase was subjected to evaporation which yielded approximately 100 percent of pure product. The product was determined to be octyl-decyl phosphoryl N-methyl sodium taurinate.
- EXAMPLE 2 A solution of 60 g. of taurine (0.48 moles) in 75 milliliters of water with 22.5 g. of potassium hydroxide, was treated with 68 g. of dioctyl phosphorochloridate (0.2 moles) with cooling and strong agitation. This mixture was allowed to react over night and was then diluted with xylene. Then the mixture was azeotropically distilled to remove water. The precipitated byproduct salt wasfiltered and washed with benzene. Since thetaurine' was used in excess, this precipitate consisted of a mixture of 47.4 g. of potassium chloride and taurine. The product, potassium-bis-(Z-ethyl hexyl) phosphoryl taurinate, as isolated from the hydrocarbon, was 89.5 g. The yield of the product was determined to be 95 percent.
- EXAMPLE 3 The potassium chloride-taurine mixture of example 2 was mixed with additional potassium hydroxide and potassium taurinate in water and was treated with dihexyl phosphoryl chloridate with bigh-speed stirring, similarly as in example 2. The product was determined to be potassium dihexyl phosphoryl taurinate.
- the solvent relative humidity control of the detergent of example 1 was tested and compared to a commercial detergent. It is reported that the best solvent relative humidity control is between 70 and percent for best soluble, and'insoluble soil removal. The best detergent holds more water while maintaining the solvent relative humidity at these optimum values.
- the detergent of example l was added to a perchloroethylene solvent system and also to a naphtha solvent system and tested in a three neck round bottom flask equipped with a suitable stirrer, a thermometer and an Aminco hydrometer sensing element. The temperature of the entire assemblies was controlled by a water bath. The tests were conducted at 75 F. Then, incremental amounts of distilled water were added to each system and after the vapor phase stabilized above the solvent system, the amount of water added was recorded when the relative humidity was between 70 percent and 80 percent. The results of these tests are tabulated below:
- the amount of water that may be added to the solvent system, using the detergent of this invention to achieve the optimum relative humidity is higher than the commercial detergents.
- the detergents of the present invention have superior solvent relative humidity control properties.
- EXAMPLE 1 The detergent of example 1 was tested for insoluble soil removal and redeposition properties. This test measures the ability of the dry cleaning detergent test solutions to remove insoluble soils which are bound to cotton fibers by grease and oil. The test also measures the ability of these test solutions to keep the soil suspended, i.e., prevent its being redeposited upon the clean cloth during the washing cycle.
- standard test swatches from F. D. Snell both soiled and unsoiled, were conditioned in a desiccator at 75 percent relative humidity for several days. The relative humidity of the test fabric was 75 percent when the clothes were placed into the washer. The test solution had a solvent relative humidity of 75 percent at the start of the washing cycle. The ratio of fabric to solvent used was 1 g.
- test swatches were obtained for this test.
- the test technique used is substantially the same as that outlined in example 5 The differences were that the test swatches contain a standard amount of sugar.
- the dry cleaning cycle was for 15 minutes rather than 45 minutes. After the swatches were air dried for 12 hours, the remaining sugar in the swatches was dissolved in water and titrated directly. The results are reported as percent sugar removed.
- R is an alkyl group containing from six to 16 carbon atoms
- R is an alkyl group containing from six to 16 carbon atoms
- R is hydrogen or methyl an alkyl group containing from one to eight carbon atoms
- Y is selected from the group consisting of sodium and potassium and mixtures thereof
- n is an integer from one to four.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Detergent Compositions (AREA)
Abstract
WHEREIN R is an alkyl group containing from six to 16 carbon atoms; R1 is an alkyl group containing from six to 16 carbon atoms; R2 can be hydrogen, an alkyl group containing from one to eight carbon atoms or an aryl group containing from one to eight carbon atoms; Y is selected from the group consisting of sodium, potassium, ammonium and mixtures thereof, and n is an integer from one to four.
A composition of matter useful in the process of dry cleaning clothing consisting essentially of the formula:
A composition of matter useful in the process of dry cleaning clothing consisting essentially of the formula:
Description
United States Patent [72] inventor Ralph B. Fearing Bardonia, N.Y. [2]] Appl. No. 686,747 [22] Filed Nov. 29, 1967 {45] Patented Dec. 7, 1971 [73] Assignee Stauifer Chemical Company New York, N.Y.
[54] DIALKYL PHOSPl-IORYL N-ALKYLTAURINATES 1 Claim, No Drawings [52] U.S. Cl 260/947, 8/142, 260/984 [51] Int. Cl C07f 9/24, D061 H04 [50] Field of Search 260/947, 920
[56] References Cited UNITED STATES PATENTS 3,298,937 ll/l967 Strauss et a] 260/947 X Primary ExaminerCharles B. Parker Assistant E.raminerAnton H. Sutto Attorneys-Daniel C. Block, Robert C. Sullivan, Donald M.
MacKay and Paul J. Juettner ABSTRACT: A composition of matter useful in the process of dry cleaning clothing consisting essentially of the formula:
ROORz wherein R is an alkyl group containing from six to 16 carbon atoms; R is an alkyl group containing from six to 16 carbon atoms; R can be hydrogen, an alkyl group containing from one to eight carbon atoms or an aryl group containing from one to eight carbon atoms; Y is selected from the group consisting of sodium, potassium, ammonium and mixtures thereof, and n is an integer from one to four.
1 DIALKYL PHOSPIIORYL N-ALKYLTAURINATES BACKGROUND OF THE INVENTION In the art of dry cleaning clothing, it is the practice to place the clothing in a solvent system and saturate or otherwise agitate the clothing therein. The solvents commonly used are 70-80 percent can be maintained at a maximum water content without fabric shrinkage or wrinkling;
e. remove insoluble soils and minimize their redeposition on clothes,
remove water soluble soils such as sodium chloride and sugars, thereby preventing visual or cumulative redeposition on the clothes;
g. allow dissipation of static charge, particularly in tumbler dryers; to avoid shock to personnel; to avoid lint problems; and allow easy garment handling and pressing;
h. be nontoxic in formulation and in use;
i. be harmless to textile dyes.
It is common practice to add up to about percent by weight of detergents such as amine alkyl aryl sulfonate, an anionic phosphate ester such as the well known alkyl aryl polyoxyethylene phosphates, or sodium dioctyl sulfosuccinate to the solvent system. However, these detergentshave failed to fill all the above noted requirements of a detergent in sol- BRIEF DESCRIPTION OF THE INVENTION It has been discovered that dialkyl phosphoryl N-alkyl taurinates provide superior cleaning properties when employed as a detergent within the commonly employed solvent systems. Compounds of the present invention are represented by the following formula:
P-N-(GHzh-SOgY wherein R can be an alkyl group containing from six to 16 carbon atoms; R can be an alkyl group containing from six to 16 carbon atoms; R can be hydrogen, an alkyl group containing from one to eight carbon atoms or an aryl group containing from one to eight carbon atoms and Y can be sodium, potassi um or ammonium and n can be an integer from one to four. It has been found that the above compound is provided with all the properties that are required of detergents employed in the common solvent systems as above noted. The amount of materials of the present invention that can be employed with the solvent system may range between 0. l0 to 10.0 percent by weight.
DETAILED DESCRIPTION OF THE INVENTION In the practice of the present invention, the dialkyl phosphoryl N-alkyl taurinates are formulated by first reacting phosphorus trichloride with an alkyl alcohol to form a dialkyl phosphite. The alcohols that may be used may be methanol, ethanol, propanol, isopropanol, butanol, and isobutanol. Thereafter, the dialkyl phosphite may be reacted with another alcohol containingfrom six to 16 carbon atoms to produce transesteritication to the higher molecular weight phosphite. ester. The reaction product is then chlorinated to produce the corresponding dialkyl phosphorochloridate. Thelatter intermediate is then reacted with sodium or potassium N-alkyl taurinate or a homolo gthereof, in a manner well known in the art, producing the final product in high yield.
It has been found in practice that from 0.10 to 10.0 percent by weight can be added to the commonly used perc hloroethylene, naphtha, carbon tetrachloride, trichloroethylene or trichloroethane systems to provide superior cleaning properties to the solvent systems.
In order to illustrate the merits of the present invention, the following examples are provided:
EXAMPLE 1 A 500 g. solution of 65 percent N-me'thyl sodium taurinate (46 percent excess over 2 mole proportions) was treated at 20 C., with octyl decylphosphorochloridate and toluene by adding the same over a period of L5 hours and then stirring the same at 25 C., for 2 additional hours. The solids and aqueous byproducts were separated by centrifuging. Thereafter, the solution phase was subjected to evaporation which yielded approximately 100 percent of pure product. The product was determined to be octyl-decyl phosphoryl N-methyl sodium taurinate.
EXAMPLE 2 A solution of 60 g. of taurine (0.48 moles) in 75 milliliters of water with 22.5 g. of potassium hydroxide, was treated with 68 g. of dioctyl phosphorochloridate (0.2 moles) with cooling and strong agitation. This mixture was allowed to react over night and was then diluted with xylene. Then the mixture was azeotropically distilled to remove water. The precipitated byproduct salt wasfiltered and washed with benzene. Since thetaurine' was used in excess, this precipitate consisted of a mixture of 47.4 g. of potassium chloride and taurine. The product, potassium-bis-(Z-ethyl hexyl) phosphoryl taurinate, as isolated from the hydrocarbon, was 89.5 g. The yield of the product was determined to be 95 percent.
EXAMPLE 3 The potassium chloride-taurine mixture of example 2 was mixed with additional potassium hydroxide and potassium taurinate in water and was treated with dihexyl phosphoryl chloridate with bigh-speed stirring, similarly as in example 2. The product was determined to be potassium dihexyl phosphoryl taurinate.
Since a certain amount of water is desirable in dry cleaning systems for optimum cleaning, the solvent relative humidity control of the detergent of example 1 was tested and compared to a commercial detergent. It is reported that the best solvent relative humidity control is between 70 and percent for best soluble, and'insoluble soil removal. The best detergent holds more water while maintaining the solvent relative humidity at these optimum values. Thus, the detergent of example l was added to a perchloroethylene solvent system and also to a naphtha solvent system and tested in a three neck round bottom flask equipped with a suitable stirrer, a thermometer and an Aminco hydrometer sensing element. The temperature of the entire assemblies was controlled by a water bath. The tests were conducted at 75 F. Then, incremental amounts of distilled water were added to each system and after the vapor phase stabilized above the solvent system, the amount of water added was recorded when the relative humidity was between 70 percent and 80 percent. The results of these tests are tabulated below:
alkyl aryl lull'onate 'An isopropyl amine salt of dodccylbenzenesulfonic acid sold under the Trade mark ATLAS G-7ll.
By comparing the results of the above tests with commercial detergents, the amount of water that may be added to the solvent system, using the detergent of this invention to achieve the optimum relative humidity, is higher than the commercial detergents. Thus, the detergents of the present invention have superior solvent relative humidity control properties.
EXAMPLE The detergent of example 1 was tested for insoluble soil removal and redeposition properties. This test measures the ability of the dry cleaning detergent test solutions to remove insoluble soils which are bound to cotton fibers by grease and oil. The test also measures the ability of these test solutions to keep the soil suspended, i.e., prevent its being redeposited upon the clean cloth during the washing cycle. Thus, standard test swatches from F. D. Snell, both soiled and unsoiled, were conditioned in a desiccator at 75 percent relative humidity for several days. The relative humidity of the test fabric was 75 percent when the clothes were placed into the washer. The test solution had a solvent relative humidity of 75 percent at the start of the washing cycle. The ratio of fabric to solvent used was 1 g. of fabric to 25 milliliters of solvent. The swatches were cleaned for 45 minutes in a closed glass container, equipped with a stirrer. After washing, the swatches were rinsed in solvents which contained no detergent, then they were air dried for 12 hours. The reflectances of the swatches were then measured. A drop in reflectance of unsoiled test swatches is a measure of soil redeposition and a gain in reflectance of the soiled swatches is a measure of soil removal. A plus change in reflectance indicates soil removal, a minus change indicates redeposition. High plus values and low minus values are the most desirable. The results of this test are tabulated below:
+33 -l5 A commercial amine l.0 Naphtha +25 -25 alkylaryl sulfonate None Naphtha 'An isopropyl amine salt of dodecylbenzenelulfonic acid sold under Trademark ATLAS G-7l lv EXAMPLE 6 The detergents of example I were tested for water soluble soil removal properties. This test measures the ability of dry cleaning detergent solvent systems to remove water soluble soil from clothing. The National Institute of Dry Cleaning, and most commercial dry cleaners have indicated that sugar removal is the most important of the water soluble soil removal properties. Good soluble soil removal is important to the cleaner because it reduces the need to spot clean certain soiled areas on garments with soap and water sprays. Thus, standard sugar impregnated rayon test swatches were obtained for this test. The test technique used is substantially the same as that outlined in example 5 The differences were that the test swatches contain a standard amount of sugar. The dry cleaning cycle was for 15 minutes rather than 45 minutes. After the swatches were air dried for 12 hours, the remaining sugar in the swatches was dissolved in water and titrated directly. The results are reported as percent sugar removed.
'An isopropyl amine salt of dodecyl enzenesulfonic acid sold under trademark ATLAS 0-7] I EXAMPLE 7 The detergents as set forth in examples 2 and 3 were tested similarly as in examples 4, 5 and 6, with the results being substantially the same.
What is claimed is:
1. (Amended Twice) A composition of the formula:
wherein R is an alkyl group containing from six to 16 carbon atoms; R is an alkyl group containing from six to 16 carbon atoms; R, is hydrogen or methyl an alkyl group containing from one to eight carbon atoms; Y is selected from the group consisting of sodium and potassium and mixtures thereof; and n is an integer from one to four.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US68674767A | 1967-11-29 | 1967-11-29 |
Publications (1)
Publication Number | Publication Date |
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US3626034A true US3626034A (en) | 1971-12-07 |
Family
ID=24757578
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US686747A Expired - Lifetime US3626034A (en) | 1967-11-29 | 1967-11-29 | Dialkyl phosphoryl n-alkyltaurinates |
Country Status (1)
Country | Link |
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US (1) | US3626034A (en) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3298937A (en) * | 1963-01-12 | 1967-01-17 | Dehydag Gmbh | Electroplating baths and processes |
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1967
- 1967-11-29 US US686747A patent/US3626034A/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3298937A (en) * | 1963-01-12 | 1967-01-17 | Dehydag Gmbh | Electroplating baths and processes |
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