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Publication numberUS2965576 A
Publication typeGrant
Publication dateDec 20, 1960
Filing dateMay 14, 1956
Priority dateMay 14, 1956
Publication numberUS 2965576 A, US 2965576A, US-A-2965576, US2965576 A, US2965576A
InventorsWilson Eugene R
Original AssigneeProcter & Gamble
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Detergent compositions
US 2965576 A
Abstract  available in
Images(5)
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Claims  available in
Description  (OCR text may contain errors)

- .chain fatty acid having -14 carbon atoms.

compounds are N-[3-bis (2-hydroxyethvl) aminonropvl] United States Patent O DETERGENT COMPOSITIONS v:l lugene R. Wilson, Whitley Bay, England, assignor to .The Procter & Gamble Company, Cincinnati, Ohio, a corporation of Ohio No Drawing. Filed May 14, 1 956,Ser. No. 584,469

11 Claims. (Cl. 252-137) The present invention relates to detergent composi- -tionscontaining additives which impart tothese detergent compositions improved sudsing characteristics at lower than usual washing temperatures and, moreparticularly,

to improvements in the sudsing characteristics of deter- ;gent compositions containing sulfated and sulfonated tures below 100 F. At these low temperatures, anionic synthetic detergents have only moderate sudsing power. "In addition, there is a tendency on the part of many persons when using a high-sudsing'type of detergent to estimate the amount of detergent to be added to a washing solution, and pariicularly a dishwashing solution, on

the basis of the amount ofsuds being formed. As a consequence, particularly when washing temperatures are below 100 R, an amount of detergent in excess of that necessary to achieve adequate detergency quite commonly will be used.

It is an object of the present invention to provide addi- -tives for anionic synthetic detergent compositions which will facilitate sudsing at temperatures below 100 F.

It is a further object to provide synthetic anionic sulfate and sulfo-nate detergent compositions which will suds at least as profusely at 60 F. as at 115 F., a conventional dishwashing temperature.

Other objects and advantageous features will appear fromthe followingdetailed dcscription.

The present invention is based on the discovery that a limited group of amides, when present in minor amounts as components of detergent compositions, ex- "hibit a remarkable abilityto increase thesudsing capacity of the synthetic anionic-sulfate and sulfonate detergents at thelower temperatures at which the more commonly employed suds-building additives aregreatly reduced in eificiency.

The low temperature suds enhancing agents which are employed alone or in combination with each other in the practice of the present invention may be represented by the following structural formulae and specific compounds:

CHzCHzOH .R-o O-NH-CHZCHZCHg-N CH CHzOH wherein R-CO is an acyl radical of a higher straight- Specific lauramide, N-[3-bis (Z-hydroxyethyl) aminopropyl] decanamide, and N-[3-bis (Z-hydroxyethyl) aminopropyflmyristamide.

These compounds can be prepared as follows: N,N-bis- (hydroxyethy1)-trimethylenediamine (1.1 moles) is added slowly, with stirring, below the surface of the fatty acid (1,0 mole) which is maintained at .165-170 F..under a 2,965,576 Patented Dec. 20, 1960 .wherein "R-CO isanacyl radical of :a higher-straight chain fatty acid having IO-l4 carbon .atoms. :Snecific compounds are N-lauroyl-N-methylglucamine, .N-decanoyl=N-methylglucamine, and Nemyristoyl-N-metbyl- @glucamine.

These compounds can be prepared as follows: yEquimolar amounts of N-methylglucamine, which;is;readily available commercially, .and a fatty acid are heated together at -170" F., with constant removal .of.-the water formed.

wherein R-NH is an amino radical and R is an alkyl radical having about 10 to about 14 carbon atoms. Specific compounds are N-keryl-D-gluconamide (the keryl group being derived from akerosense fraction containing predominantly 12 carbon atoms per molecule), N- decyl-D-gluconamide, N-dodecyl-D- gluconamide, .and N- .tetradecyl-D-gluconamide.

These compounds can be prepared as follows: Thedeltalactone of gluconic acid, which is commercially available on large scale, is prepared by crystallization from a concentrated aqueous solution of gluconic ,acid. .Alkyl amines having 10-14 carbon atoms are manufactured commercially. The alkyl amines are condensedrapidly and completely with 'glucono-delta-lactone in refluxing methanol. On cooling the solutions, ,high yields .o f the N-alkyl-D-gluconamides are obtained in the form ofpure white glistening platelets which may be recrystallized from boiling ethanol or methanol.

The individual C -C fatty acids can vbe employed in the preparation of low temperature suds-building amides of this invention as indicated above,.but mixtures of fatty acids consisting of more than 50%.ofsuch acids, such as mixed fatty acids derived from oils of thecoconut group (coconut oil, palm kernel oil, etc.) can alsobe used. Similarly, in those instances .where higher alkyl amines are employed in the preparation of the amide,

individual amines or mixtures consisting of .more..than

50% of a Clo-C14 amine can be used.

An important feature of my invention is the fact that not all amides exhibit the quality of improving the sudsing characteristics of detergents at low temperatures.

For example, the alkylolamide of monoethanolamine-a nd the fatty acids of coconut oil, hereinafter referred to;as coconut ethanolamide, is quite commonly used as .an organic suds-builder; however, its maximum efficiency as a suds-builder is observed at temperatures well .above 100 F. Because of the widespread use of coconut ethanolarnide as a suds-builder, it has been selectedas a standard for comparison with the amide .suds-buildersof nated amide. A standardized dishwashingdestprocedure was used to measure the sudsingproficiencyof the,detergent compositions after repeated exposure .to .soil ed 3v plates, and the results are expressed as percent relative to the coconut ethanolamide composition at 115 F.

It is clearly evident from the data in Table I that N- lauroyl-N-methylglucamine, N-[3-bis (2-hydroxyethyl) amino propyl] lauramide, and N-dodecyl-D-gluconamide are outstandingly superior as suds-builders to coconut ethanolamide at a dishwashing temperature of 60 F. Furthermore, it should be noted that these three sudsbuilding amides are at least equally as effective as coconut ethanolamide at the normal dishwashing temperature of 115 F. An interesting observation, however, that distinguishes the amides herein claimed is that they are more effective as suds-builders at 60 F. than at 115 F. On the basis of the performance of known amide builders, this is a new and unexpected property. The extraordinary efiicacy of these suds-builders over a wide temperature range is without question of considerable commercial importance.

TABLE I sudsing at; S lllill it; Product; ll5 F., 60 F.,

Percent Percent Coconut ethanolamide 100 80 N-La royl-N-methylglucamine.. 104 111 N-[3-Bis (2-hydroxyethyl) amin propyl] llura r idc 103 112 N-Dodecyl-D-gluconamide 100 102 The organic synthetic detergents which find use in the practice of this invention either singly or in admixture, can be generically defined as those possessing pronounced sudsing and detergent characteristics and having in the molecule an alkyl group of from about 8 to about 18 carbon atoms and a sulfate or sulfonate radical.

Water-soluble salts of sulfonic acids which exhibit detergent effect, such as the higher alkylated benzene sulfonic acids (e.g. potassium salt of the sulfonic acid derived from the condensation product of benzene and a chlorinated kerosene fraction containing predominantly l2 car- .bon atoms per molecule, or the sodium salt of the sulfonic acid derived from the condensation product of benzene and polypropylenes having from 9-15 carbon atoms and averaging about 12 carbon atoms), are greatly improved in their low temperature sudsing properties by addition thereto of a smaller amount of the amides mentioned above. Also, water-soluble salts of higher monofatty acid esters of 1,2-dihydroxy propane-3-sulfonic acid (sodium salt of the coconut oil fatty acid monoester of the sulfonic acid is a specific example) will find use in the practice of this invention. In addition, water-soluble salts of higher fatty acid monoesters of lower molecular weight hydroxyl alykyl sulfonic acids (e.g. oleic acid ester of the sodium salt of isethionic acid) and of the higher fatty acid amides of lower molecular amino alkyl sulfonic acids (e.g. ammonium salt of oleic acid amide of N-methyl taurine) may be employed. Likewise, detergent compositions which suds well at low temperatures may be prepared from synthetic detergents such as the water-soluble v salts of the higher alcohol esters of sulfocarboxylic acids {c.g. sodium salt of the lauryl alcohol ester of sulfoacetic acid) and ethers of high molecular alcohols and lower hydroxy and polyhydroxy sulfonic acids (e.g. monolauryl ether of 1,2-dihydroxy propane-3-sodium sulfonate).

Other synthetic detergents which are useful in the practice of my invention include the water-soluble salts of high molecular aliphatic sulfuric acid esters such as the alkali metal salts of sulfuric acid esters of normal primary aliphatic alcohols having twelve to eighteen carbon atoms, particularly those whose principal active ingredient is a water-soluble salt of lauryl sulfuric acid or oleyl sulfuric acid. Specific examples are the sodium alkyl sulfate obtained from the mixed higher alcohols produced by the reduction of coconut oil, palm kernel oil, or other oils of the coconut oil group (a group of tropical nut oils characterized by their high content of combined fatty acids having ten to fourteen carbon atoms) or the sodium alkyl sulfate derived from the higher alcohols of sperm oil. Also, water-soluble salts of sulfuric acid esters of higher fatty acid monoglycerides (e.g. sodium salt of the coconut oil fatty acid monoester of 1,2-dihydroxy propane-B-sulfuric acid ester) and of the sulfated higher fatty acid alkylolamides (e.g. sodium salt of sulfated coconut fatty acid ethanolamide) may be employed. Included among these synthetic detergents, also, are the water-soluble salts of higher alkyl polyethylene oxide sulfuric acid esters (e.g. the sulfated and neutralized reaction product of about three moles of ethylene oxide with one mole of a mixture of higher alcohols derived from coconut oil and having predominantly 10-14 carbon atoms).

The above examples are merely specific illustrations of the numerous detergents which can be improved in their low temperature sudsing performance when used in conjunction with the amides heretofore designated in accordance with my invention, and is not intended that the present invention be limited thereto. These detergents may be used singly or in combination, with or without the presence of auxiliary materials which may include any of the substances employed by the art in admixture with sulfated and/or sulfonated organic synthetic detergents. The various alkali metal phosphates (e.g. tripolyphosphate and higher polyphosphates, hexametaphosphate, tetrapyrophosphate, and orthophosphate), the alkali metal silicates, sulfates,v carbonates, etc. are intended to be illustrative but not preclusive examples of these auxiliary materials.

When it is desirable to incorporate an alkali metal tripolyphosphate, for example, in the detergent compositions of the present invention, any amount may be used, but if heavy-duty cleansing performance is the object, then the amount of tripolyphosphate is desirably from about 1 to 5 times the amount by weight of organic synthetic detergent salt, and preferably from 2 to 3 times.

In all such detergent compositions, the amount of amide employed to enhance the sudsing characteristics at temperatures below P. will be from about 5% to about 60% by weight of the organic synthetic detergent, and preferably from about 5% to about 35%.

Thus, in the preferred compositions of the present invention having both heavy-duty cleansing performance and superior low temperature sudsing characteristics, the amount by weight of organic synthetic detergent salt will constitute from about 10% to about 40% and preferably from about 15% to about 30% of the total composition. The amide, on the same basis, will constitute from about 0.5% to about 25% and preferably from about 0.5% to about 15%, but not more than about 60% and not less than about 5% by weight of the organic synthetic detergent salt. The amount of tripolyphosphate will vary from about 1 to about 5 times the amount by weight of the organic synthetic detergent salt. It is to be understood, of course, that the respective percentages of the above three essential constituents can be adjusted to provide for the presence of sodium sulfate, which usually accompanies unpurified sulfuric reaction products, and for the inclusion of additional constituents, such as fluorescent dyes, bleaching agents, perfumes, and other constituents adapted to impart desirable properties to the composition.

The invention will be more clearly understood from the following examples, but these examples are merely illustrative of the manner in which my invention may be practiced and are not to be construed as limitations. All parts are by weight.

Example I To 50 parts of commercial sodium alkyl benzene sulfo nate containing as active ingredient about 35% of the sodium salt of the sulfonic acid derived from the condensation product of benzene and polypropylenes having aaaaawrta 9-15 *carbon atoms .and averaging (12 carbon atoms are raadded47 parts of sodium tripolyphosphate-andl '3 parts of N-lauroyl-N-methylglucamine thus giving amixture J containing 17.5% active detergent, 32.5%:sodium sulfate,

-'47% sodium tripolyphosphate land 3% ':NlauroylN- 3. .tmethylglucamine withsodium tripolyphosphate :to active .detergent in a ratio of 2.7: 1. This mixture is. superior in *sudsing in the.dishpan at "temperatures of: 60 :F. .tothe detergent and tripolyphosphate alone and --to :a :similar i-suds-builder.

Example II To partsof commercial sodium alkyl sulfate (37.5%

active ingredient and 62.5% sodium sulfate) prepared 1 from higher alcohols obtained by the reduction of coconut oil and containing predominantly 10-14 carbon atoms are added 62 parts of sodium tripolyphosphate and 3 parts of N-lauroyl-N-methylglucamine. This mixture contains the sodium tripolyphosphate and active alkyl sulfate in the ratio of about 4.7 to 1 andN-lauroyl-N-rnethylglucamine in an amount equivalent to 3% of the total product. This mixture of sodium alkyl sulfate, rsodium tripolyphosphate, sodium sulfate, ,and N-lauroyl-N-methylglucamine exhibits highly desirable sudsingcharacteristics at :7 -.temperatures of .60 F., superior to those characteristics ,possesed .by a comparable mixture containing coconut .oil .ethanolamide as the suds-builder.

Example III phate and3'parts of N-lauroyl-N-methylglucamine thus giving a mixture containingl part of activesynthetic detergent to about 2.7 parts of sodium tripolyphosphate andN-lauroyl N-methylglucamine in an amount "equivalent to 3% of the composition. This mixture isgreatly .superior in sudsingproficiency at F. to a comparable preparation containing 3% coconut ethanolamide instead .of N-lauroyl-N-methylglucamine.

The following compositions are also productive of the desired results.

Example IV Percent Sodium alkyl benzene sulfonate (the sodium salt of the sulfonic acid derived from the condensation product of benzene and polypropylenes having 9-15 carbon atoms and averaging 12 carbon atoms) 18 N-lauroyl-N-methylglucamine ,L 1 Sodium sulfate 34 Sodium tripolyphosphate 47 vExample V Percent Sodium kerylbenzene sulfonate (the sodium'salt of thesulfonic acid derived from the condensation product of benzene and a chlorinated kerosene "fraction containing predominantly 12 carbon atoms per molecule) a '10 Sodium lauryl sulfate 7.5 N-[3-bis(2-hydroxyethyl) aminopropyl] lauramide 3 Sodium sulfate 32.5

, .Sodium .tripolyphosphate 47 Example VI Percent :Sodium coconut alcohol sulfates (from a fractionated mixture of coconut oil alcohols consisting predominantly of C to C fatty alcohols) 17.5 N-dodecyl-D-gluconamide 6 Sodium sulfate 32.5 Sodium tripolyphosphate 44 preparation containing 33% coconut ethanol aamideasithe T detergent composition. .tures may be manufactured and maybe preferablefor ,many purposes, it is likewise withinthe scope of my inventionto. add the low temperature suds-building amides to water prior tothe adding of the detergent alone or film :the abovewcxamples,amides; having tenor fourteen .carbonpa'toms in the acyl or alkyl radicals .HlfiYrbEgSllb' xstituted 'with substantially equal results.

tMy invention is not limited to any particulanmethod .of mixing the low "temperature suds-building amideswith the sulfate and sulfonate detergents withor without alkali .:metal tripolyphosphate. They may be incorporated in' the detergent compositions in any .of the forms in which these compositions are manufactured. The low temperature suds-building amides may be mechanically mixed in; may be crutched into the detergentcomposition in the form of a slurry;.,andmay be= dissolved in a solution of the While. such ready-for-use mixdetergent and alkali metal tripolyphosphate or vice versa,

.or toadd detergent and amide or detergent, amide and .alkali metal tripolyphosphate simultaneously but msepa rately.,to the water.

What is claimed is:

1. A cleansing .anddetergent composition consisting essentially of a mixture of at least one water-soluble salt of an organic sulfuric reaction product having in its .molecular structure an alkyl group of from about 8 to .about 18 carbon atoms and aradical selected from the .group consisting of sulfonic acid and sulfuric acid, the, said .salt having pronounced detergent power, and at least one amide. selected frornthe group consisting of:

R-NHC,O-(CHOH) CH OH wherein RCO is an acyl radical of a fatty acid having about 10 to about 14 carbon atoms and R-NH is an amino radical and R is an alkyl radical having from about 10 to about 14 carbon atoms, the amount by weight of the-amidebeing fromabout 5% to about 60% of the amount by weight of said water-soluble salt and sufficient to-enhance, at temperatures below F., the sudsing properties of said water-soluble salt.

*2. *The cleansing and detergent composition'of claim 1 containingan amount by weight of said amide of from about 5% to about 35% of the amountbyweight of said water-soluble salt.

3. A cleansing and detergent composition consisting -essentially of a mixture of at least one water-soluble salt of an organic sulfuric reaction producthaving in its molecular structure an alkyl group of from about 8 to about 18 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid, the said salt having pronounced detergent power, and an amide having the following structural formula:

omomorr R-o earn-emerncmn omcmou 5. A cleansing and detergent composition consisting essentially of a mixture of at least one water-soluble salt of an organic sulfuric reaction product having in its molecular structure an alkyl group of from about 8 to about 18 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid, the said salt having pronounced detergent power, and an amide having the following molecular structure:

wherein R-CO is an acyl radical of a fatty acid having from about 10 to about 14 carbon atoms, the amount by weight of the amide being from about to about 35% of the amount by weight of said water-soluble salt,

and sufficient to enhance, at temperatures below 100 F., the sudsing properties of said water-soluble salt.

6. The cleansing and detergent composition of claim 5 in which said water-soluble salt having pronounced detergent power is a mixture of water-soluble salts of alkylated benzene sulfonic acids having predominantly 9 to 15 carbon atoms in the alkyl group.

7. A cleansing and detergent composition consisting essentially of a mixture of at least one water-soluble salt of an organic sulfuric reaction product having in its molecular structure an alkyl group of from about 8 to about 18 carbon atoms and a radical selected fro-m the group consisting of sulfonic acid and sulfuric acid, the said salt having pronounced detergent power, and an amide having the following molecular structure:

wherein R-NH is an amino radical and R is an alkyl radical having from about to about 14 carbon atoms, the amount by weight of the amide being from about 5% to about 35% of the amount by weight of said watersoluble salt and sufiicient to enhance, at temperatures below 100 F., the. sudsing properties of said water-soluble salts.

8. The cleansing and detergent composition of claim 7 in which said water-soluble salt having pronounced detergent power is a mixture of water-soluble salts of sulfated benzene sulfonic acids having from 9 to carbon atoms in the alkyl group.

9. A cleansing and detergent composition consisting essentially of from about 10% to about 40% by weight, based on total product, of a mixture of water-soluble alkyl benzene sulfonate detergents, having from 9 to 15 carbon atoms in the alkyl group, an alkali metal tripolyphosphate in an amount by weight of from about 1 to about 5 times the amount by weight of said alkyl benzene sulfonate, and at least one amide selected from the group consisting of:

" wherein R- -CO is an acyl radical of a fatty acid having from about 10 to about 14 carbon atoms, R-NH is an amino radical and R is an alkyl radicalhaving from detergent, and sutficient to enhance, at temperatures below F., the sudsing properties of said alkyl benzene sulfonate detergent.

10. A cleansing and detergent composition consisting essentially of from about 15% to about 30% by weight, based on total product, of a mixture of water-soluble alkyl benzene sulfonate detergents, having from 9 to 1-5 carbon atoms in the alkyl group, and alkali metal tripolyphosphate in an amount by weight of from about 2 to 3 times the amount by weight of said alkyl benzene sulfonate, and at least one amide selected from the group consisting of:

CHzCHzOH R-C ONHCH2CHCH,N

CHzCHgOH CH: R-C O-N CHACHOHMCHIOH and wherein R-CO is an acyl radical of a fatty acid having from about 10 to 14 carbon atoms, R-NH is an amino radical and R is an alkyl radical having from about 1 0 to about 14 carbon atoms, the amount by weight of the amide being from about 5% to about 35% of the amount by weight of said alkyl benzene sulfonate detergent, and sufficient to enhance, at temperatures below 100 F., the sudsing properties of said alkyl benzene sulfonate detergent. j

11. A laundering composition having improved sudsing performance in aqueous solution at temperatures below 100 F., consisting essentially of (a) about 10% to about 40% by weight, based on total product, ofla water-soluble salt of an organic sulfuric reaction product having in its molecular structure a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals, the said salt having pronounced detergent power; (b) from about 0.5% to about 25%, based on the total product, but not more than 60% and not less than 5% by weight of the organic synthetic detergent salt, of at least one amide selected from the group consisting of:

CHQCHQOH R-C O-NH-CHzCHzC'HzN cmCmoH R-C ON CHflCHOHhCHgOH and to about 14 carbon atoms; and (c) the balance of the composition comprising alkali metal tripolyphosphate in amount from about 1 to about 5 times the amount b weight of the alkyl benzene sulfonate. I

References Cited in the file of this patent UNITED STATES PATENTS 1,952,008 Bruson Mar. 20, 1934.- 1,985,424 Piggott Dec. 25, 1934 2,486,921 Byerly Nov. 1, 19 49 2,662,073 Mehltretter Dec. 8, 1953 2,703,798 Schwartz Mar. 8, 1955 UNITED STATES PATENT OFFICE CERTIFICATION OF CORRECTION Patent No. 2,965.5 6 December 20, 1960 Eugene R. Wilson It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.

Column 7, lines 60 to 63, and column 8, lines 17 to 20 the formula should appear as shown below instead of as 1n the patent:

/CH I W R-CO-N' CH (CHOH;) CH OH column 8, line 25, after "to" insert about -c Signed and sealed this 24th day of October 1961,

(SEAL) Attest:

ERNEST W. SWIDER DAVID o LADD Attesting Officer Commissioner of Patents

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Classifications
U.S. Classification510/357, 510/502, 510/496, 510/359, 510/350
International ClassificationC11D3/066, C11D1/38, C11D1/52, C11D3/06
Cooperative ClassificationC11D3/0094, C11D3/066, C11D1/525
European ClassificationC11D3/066, C11D1/52H, C11D3/00B19