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
  • C11D1/38—Cationic compounds
  • C11D1/65—Mixtures of anionic with cationic compounds
  • C11D1/655—Mixtures of sulfonated products with alkylolamides of carboxylic acids
• • 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
  • C11D1/38—Cationic compounds
  • C11D1/65—Mixtures of anionic with cationic compounds
  • C11D1/652—Mixtures of anionic compounds with carboxylic amides or alkylol amides
• • 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
  • C11D3/43—Solvents
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
  • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
  • Y10S516/07—Organic amine, amide, or n-base containing

Definitions

• the a'nionic sulfate and sulfonate detergents herein referred may be even solids at normal temperatures; 'In the. molten state, they are usually highly viscous 2.
• Selective soZvnt.'-The l iquid media which maybe employed must ne'cessarilybe selectivein action. It should be somewhatimiscible or soluble with Water; render'ahigh degree 'of fluidity to the composition; havesolubili'zing eflfeots on'thedetergents, permit adequate concentration-"of solids,
• Foaming The compositionishould yield a good volume of foam with a high-degree of'ifoam stability i during washing operations.
• The' foam should be ofgo'od creaminess Of'COIlSi'SlJEllCYfllOll large measure due to the amount of soil removed.
• Grease emulsificati-on.-It shouldpossess the ability'to' 'emulsify readily' fats, oils, greases-land the like in order. to facilitate removal of the same washing operations, particularly dishWa-sh-ing.
• Soil 'removalr-The detersive eificiency islin "Thecomposition-should exhibit a high level; of soil removal'power, particularlyin Washing o'tfine fabrics, dishwashing,v andthe like.
• composition should preferablypossess such solubility characteristics that a-concentratedsolution may ordinarilygbe 1 preparedwfornuse whereby v a relatively small .-amount may lac-conveniently utilized. by the con- .su'mer and yet beadequate .for many uses.
• the incorpoif a" suitable synthetic deteranionic sulfated 'and sulfon'ated detergentsare efiective" to achieve a significant and'synergistic present invention comprises a liquid detergent composition consistingi'essentiallyr of" the-water soluble anionic fs'ulfated' or sulfonate'd detersive alkylolamide eifective'to enhance the action of the detergent composition in aqueous solution, and a solubilizing diluent.
• the enhancing additives of the'.present invention are characterized by their weakly polar 112w.
• the hydroxyalkyl groups may be monoor polyhydroxy alkyl.
• suitable additives are N,N'bis (2 hydroxyethyl) laur- 'amide, N,N bis (2 hydroxyethyl) myristamide,
• dialkylolamides may be prepared in any "suitable manner and numerous processes for their production are well known in the art.
• a convenient and economical mode of synthesis involves the condensation of the higher fatty acylating compounds (e. g. lauric acid, lauric acid halide, etc.) with a suitable amino compound to produce a reaction product having the desired amide structure.
• the higher fatty acylating substances may be derived from pure, impure or commercial grades ofcapric, lauric or myristic acids and the like. More particularly, these acids may be produced from fatty oils, fats, greases, and other natural sources or be of synthetic origin as derived from the oxidation of hydrocarbons. According to its origin and the degree and manner of purification, capric, lauric and myristic acids may be commonly admixed or associated with other fatty acids of higher and lower molecular weight. It is within the scope of the invention that the capryl,
• lauroyl and myristoyl compounds may be associated with other fatty substances and the like provided the character and amount of such'other materials are not sufllcient to substantially neutralize or materially affect the enhancing power of the additives in the relationship set forth.
• the commercially pure capric, lauric and myristic acids having a concentration of such acids of about 90% and above.
• a typical composition of commercially pure lauric acid may be 90% lauric acid, 9% myristic acid, 1% unsaturated acids,
• Another suitable fatty acid mixture is topped coconut oil fatty acids produced by the removal of a low-boiling fraction
• dialkylolamines may be utilized in pure, impure, or commercial form.
• dialkylolamide According to the circumstances of manufacture of the dialkylolamide, it may be chemically and/or physically associated with other materials .such .as soap, free alkylolamine, piperazine type derivatives, etc. The presence of varying amountsof such materials and the like in admix- .ture with dialkylolamide is contemplated within r the scope of the present invention, provided the same are not significant enough to materially neutralize or substantially adversely affect the desired improvements to be accomplished with the combination of the anionic detergent and the dialkylolamide additive.
• reaction product of the higher fatty acylating substance and the dialkylolamine comprising the desired dialkylolamid-e-and other derivatives as produced under certain conditions may be utilized with marked success as additives in'the novel compositions of the present invention.
• the product is to be produced by the condensation of the suitable'higher fatty acids or their equivalent with an "equivalent or an excess of dialkylolamine, the molar ratio being from about 1 :1 to about lzl-O but preferably up to about 1:5 and usually from about 1': 2 ⁇ to about 1:3, at from about 100 C. to about 200' C., and
• a typical suitable reaction mixture cited for illustrative purposes and resulting from the condensation of commercially distilled lauric acid in purity and commercial diethanolamine contains the following components on a solids basis: diethanolamide about (35 diethanolamine soap about 10%, free amine, diethanolpiperazine and minor amounts of possibly other substances
• diethanolamide about (35 diethanolamine soap about 10%, free amine, diethanolpiperazine and minor amounts of possibly other substances
• aliphatiq agentsh such -asthe l aliphatic, acyl containing compounds wherein the acyl radical has about 8 to about 22 carbon atoms, and more particularly, the, aliphatic carboxylic ester type, containing. at least about 10 and preferably about 12;;to; about 26 carbon atoms. to the molecule.
• the aliphatic detersive compounds it is particularly preferred that the aliphatic detersive compounds, it
• propylene may be polymerized to the tetrarnen and Icondensed with :henzene in the.
• Eriedelecraitsszi catalyst-to- I yield essentially the dode'cy-l benzene derivatiyawhich is is'uitable .fonlisulionaticziv torthegtidesired sulfat. a typarticularly, it. is, preferred to, use the. mono,-
• suitable .solvent may be employed as the liquidrmedium Itshould possess several. essential characteristics:sincelit functions necessarily. as,ian .,integral part, of the composition. Beside its..chemical.inertness, itniust have .a. solubiliz; ing. aetionflon the solids. It should'possess a.
• a liquid. solvent medium may.
• The. alcohols shouldpreferably bethe saturated aliphatic type ⁇ they. may. be, monoor polyhydric. in character, and.may. contain inert .solubilizing. groups, suchlasetherlinkages. suitable. exampl e ethyl alc h -s' nrl alcohol, isopropylalcohol, nebutylfalcoholl. In. comparison. tovv ethyl alcohol and. the I like,.'..the. higher alcohols such, as butanol andthellike-arenot prei'erred since. the latter Qhafye in general. a comparatiyelyfundesirable. odor. andlessv semi; bility inwater.
• Additional suitable solventsgqf. the polyhydric alcohol type arev ethylene. glycol, propyl e l c l. lycero e a Alcoho po s sse ing,ether linka es are monomethyl ether. ofethylene glycol,v monoethyl ether vof. ethylene glycol, diethylene glycol, diethyleneglyeol mono ⁇ . ethyl ether. monobutyl ether of diethyleneelycol, monomethyli ether of,.die thylene-, glycol, dioxan. etc. It is preferred to, uselwater,thealiphatic. monohydric alcoholsand the dih'ydric alcohols. bfll t 3w.
• Thegdialkylolamide maybe incorporatedw the anionic detergent atahlt. point, during. the. manufacturing process, atmv'vhi ch subsequent. op.-.- er ations will not. adversely modify the properties; of the detergent compositions.
• cedures are the, meltil of. the, dialkylolaojn an rinait into 'a;',, r. W r. t r ne. alcohol, or alcQholsolut-ion of thedetergen -orlf the dissolvingoithe additive. in alcohol or water and: stirring themixturelinto. the. anionic .de-
• the anionic detergent should be from about 30% to about 90% depending upon the solvent power, and preferably. at least about 40%. More particularly, it is preferred that the anionic detergent be at least about 30 and generally from about 40-60%, with the concentration of dialkylolamide usually at least about 10% and preferably from about 10 to about 20%. Where these solids are not sufficiently soluble in water alone for example, their solubility may be appropriately improved by the use of a mixed solvent medium, e. g. water and ethyl alcohol. While'it is preferred to prepare these compositions in the form of a concentrated solution as indicated above whereby the consumer may utilize the same conveniently and economically, it is within the scope of the invention that these compositions may be further diluted and be useful for many purposes, e. g. window, walls, woodwork, car washing, etc.
• the novel compositions of the present invention are characterized by increased stability of the foam produced in washing operations in comparison to the foaming effects produced by the compositions without the dialkylolamide.
• the foam of the compositions containing an 'anionic-dialkylolamide combination have good creaminess and consistency, do not readily break down by evaporation, have in general a long drainage time and contain an increased amount of liquid.
• the rate of foam decrease is consideraby slower ethanolamine salto'f dodecyl benzene sulfonate' with a minor amountof triethanolamine sulfate,
• composition II consists of,
• Composition III cnotains the desired combination of I and II, namely', 52 parts anionic active ingredient, 13 parts 'l'a'uroyl diethanolamide, and the remainder being the water-ethyl alcohol solvent. The tests are conducted in soft water at'11'5 F.
• compositionI Composition Per Cent I Triethanolamine salt of dodecyl benzene sulionate (52 parts) Lauroyl diethanolamide (13 parts) III Triethanolamine salt of dodecyl benzene sulfonate (52 parts) +lauroy1 diethanolamide (13 parts)
• compositions of the present invention '(e. g. composition III) is evident fromthe data. It is clear that the combinationachieves a sy ergistic enhancement in foam duration and resistance to greasy soil in comparison to the effects obtained by the individualuse of identical amounts of the components. f
• Table IIH indicates the results obtained in similar dishwashing operations in hard water (300 p. p. m.) at 115 F. of Composition III above containing the anionic detergent-qdialkylolamide.
• exhib t cloud point erosionas appmximate y yields ahighl level of 'creaminessiandlioam st 6036) I n-"proionged-chiiiirig and a; clear point ii bility infcorriparison to the relativelyrfiimsy sud of afb'out 35 -Cori slow warming; The stability mg power exhibitedi .by; the.
• compositions by means of a foam conof a 60% solution of thesame anionic detergent sistency test
• this test consists of the I withontiadded dialkylolamidat various indicated fdfmvaiiiofl'ofia f am' y'f fi aidi f t j' totai condentrationsof the detergent.compositions of 500 cc'fof adetergent'at 110F.'ina twoquart in distil'ldiwaterf v unsihfered' Dewar flaskg The' foani formed after TabZelV..-
• the deh Synergistic QR PVQIWWPSZP detergency grees through which the spring may be twisted ilgeg ip the 9 the mixed anionic-dibefore the paddle startsto move in the foam may a aide qqme ea en 1 g a hica ly rev siee v; be readily determined.
• An indicator needle is r em hemdata attachedito .the top of" the paddle-shaitand 1a .cir-j 1 Example. :7
• Example IV An impr v di u d j n h t deter eh so positionisjprenared by, ,r' iiiingtkie ingredient o g
• Example "I" Withth' modificationthata r I P61 g; q fli' 'sj acid diethanolaminereactionniixture gprepa ed
• Toppedffcooonut oil fatty. acids are e ir'i t- 7?5'.
• n i Composition anionic dialkylolamide detergent composition '75 aslow cooling process which involves cooling tfi 11 mixture with water at 120 F. circulating in a jacket, the mixture being agitated during this time, When the mixture reaches about 120 F.
• Example V The process of Example III is repeated with the modification that the dialkylolamide reaction mixture is made in accordance with the following procedure.
• Commercial lauric acid is melted and commercial diethanolamine is added with agitation till a 1 :2 molar ratio is reached.
• the reaction mixture is heated at 140-160 C. under vacuum. At this temperature, distillation of water occurs until the acid or soap content has been reduced to a value equivalent to 4.35%, calculated as diethanolamine laurate.
• the reaction product is rapidly run out of the reactorwith cooling and permitted to cool gradually.
• Example VI Per cent Triethanolamine salt of lauryl sulfate 25 Triethanolamine salt of dodecyl benzene sulfonate 25 N,N bis (2,3 dihydroxypropyl) myristamide 15 Water 15 Ethyl alcohol 20
• Example VII I Per cent Ammonium salt of higher fatty acid monoglyceride sulfates derived from coconut oil 50 Myristoyl and lauroyl diethanolamide -(1:1)
• a concentrated liquid detergent composition consisting essentially of water-soluble detergent selected from the class consisting of water-soluble salts of anionic sulfated and sulfonated de tergents having a long aliphatic chain of 8 to 22 carbon atoms, and adialkylolamide compound represented by the formula:
• R-CO is a fatty acyl radical of 10 I to 14 carbon'atoms, and R and R.” are hydroxyalkyl groups of up to about 5 carbon atoms each, the ratio of said dialkylolamide compound to anionic detergent being from about 1:10 to about 2:1 by weight, and said dialkylolamide and anionic detergent together being at least about 30% by weight in .a selective liquid solvent therefor.
• a concentrated liquid detergent composition consisting essentially of water-soluble salt of higher alkyl mononuclear aryl sulfonate detergent, said higher alkyl group having 8 to 22 carbon atoms, and a dialkylolamide compound represented by the formula:
• R-CO- is a fatty acyl radical of 10 to 14 carbon atoms
• R and R are hydroxyalkyl groups of up to about 5 carbon atoms each, the ratio .of said dialkylolamide compound to anionic detergent being from about 1:10 to about 2:1 by weight, and said dialkylolamide and anionic detergent together being at least about 30% by Weight in a selective liquid solvent therefor.
• a concentrated liquid detergent composition consisting essentially of water-soluble salt of higher alkyl, benzene sulfonate detergent, said higher alkyl group having 8 to 22 carbon atoms. and a diethanolamide compound represented by the formula:
• R,CO is a saturated fatty acyl radical of 10 to 14 carbon atoms, the ratio of said diethanolamide compound to anionic detergent being from about 1:10 to about 2:1 by weight, and said diethanolamide and anionic detergent together being at least about 40% by 'weight'in a selective liquid solvent therefor.
• a concentrated liquid detergent composition consisting essentially of anionic detergent selected from the class consisting of water-soluble salts .of anionic sulfated and sulfonated detergents having a; long aliphatic chain of 8 to 22 carbon atoms, and a dialkylolamide compound represented by the formula:
• RCO is a fatty acyl radical of 10 to 14 carbon atoms, and R and R, are hydroxyalkyl groups of up to about carbon atoms each,
• fatty acyl radical is myristoyl and the hydroxalkyl groups have 2 to 3 carbon atoms each.
• a concentrated liquid detergent composition consisting essentially of anionic detergent selected from the class consisting of water-soluble salt of anionic sulfated and sulfonated detergents having a long aliphatic chain of 8 to 22 carbon atoms, and a diethanolamide compound represented by the formula:
• Rr-CO is a saturated fatty acyl radical of to 14 carbon atoms, the ratio of said diethanolamide compound to anionic detergent being from about 1:10 to about 2:1 by weight, and said diethanolamide and anionic'detergent together being at least about 40% by weight in a selective liquid solvent therefor comprising a low molecular weight aliphatic alcohol.
• a concentrated liquid detergent composition consisting essentially of water-soluble salt of higher alkyl benzene sulfonate detergent, said higher alkyl group having 8 to 22 carbon atoms,
• Rr-CO-' is a saturated fatty acyl radical of 10 to 14 carbon atoms, the ratio of said diethanolamide compound to anionic detergent being from about 1:10 to about 2:1 by weight, and said diethanolamide and anionic detergent together being at least about 40% by weight in a selective liquid solvent therefor comprising a low molecular weight aliphatic alcohol.
• a concentrated liquid detergent composition consisting essentially of a solution of a mixture of anionic detergent selected from the class consistin of water-soluble salts of anionic sulfated and sulfonated detergents having a long aliphatic chain of 8 to 22 carbon atoms, and a dialkylolamide compound represented by the formula:
• RCO is a saturated fatty acyl radical of 10 to 14 carbon atoms
• R and R" are hydroxyalkyl groups of up to about 5 carbon atoms each, the ratio of said dialkylolaminde compound to anionic detergent being from about 1:7 to about 1:1 by weight, and said dialkylolamide and anionic detergent together being at least about 30% by weight in a selective liquid solvent phase therefor comprising water and an aliphatic saturated lower monohydric alcohol.
• a concentrated liquid detergent composition consisting essentially of a solution of a mixture of anionic detergent selected from the class consisting of Water-soluble salts of anionic sulfated and sulfon-ated detergents having a long aliphatic chain of 8 to 22 carbon atoms, and a diethanolamide compound represented by the formula:
• RCO is a saturated fatty acyl radical of 10 to 14 carbon atoms, the ratio of said diethanolamide compound to anionic detergent being from about 1:10 to about 2:1 :by weight, and said diethanolamide and anionic detergent together being at least about 40% by weight in a selective liquid solvent phase therefor comprising water and an aliphatic saturated lower monohydric alcohol mixture.
• a concentrated liquid detergent solution in accordance with claim 11 which contains sodium salt of said water-soluble anionic detergent.
• a concentrated liquid detergent solution in accordance with claim 11 which contains an ethanolamine salt of said water-soluble anionic detergent.
• a concentrated liquid detergent solution in accordance with claim 11 which contains ammoizium salt of said water-soluble anionic deteren PETER T. VITALE. RALPH SPENCER LEONARD.

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Detergent Compositions (AREA)
• Cosmetics (AREA)

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Citations (2)

• 0
  • US US23840D patent/USRE23840E/en not_active Expired
  • BE BE502985D patent/BE502985A/xx unknown
• 1950
  • 1950-05-03 US US159854A patent/US2607740A/en not_active Expired - Lifetime
• 1951
  • 1951-03-03 FR FR1035745D patent/FR1035745A/fr not_active Expired
  • 1951-04-18 GB GB9063/51A patent/GB708000A/en not_active Expired
  • 1951-05-02 CH CH300865D patent/CH300865A/de unknown

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