US3775349A - Detergent formulations containing alkyl polyethoxy sulfate mixtures - Google Patents

Detergent formulations containing alkyl polyethoxy sulfate mixtures Download PDF

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US3775349A
US3775349A US00050796A US3775349DA US3775349A US 3775349 A US3775349 A US 3775349A US 00050796 A US00050796 A US 00050796A US 3775349D A US3775349D A US 3775349DA US 3775349 A US3775349 A US 3775349A
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sulfate
alkyl
percent
sulfates
ammonium
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M Tuvell
C Yancey
R Gorsich
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Ethyl Corp
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    • 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
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • 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
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
    • 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

Definitions

  • FIG. 2 ALKYL GROUPS 0 (AS SULFATES) LC /Q 23/32 v c ALKYL V c ALKYL GROUPS GROUPS AS SULFATES) (AS SULFATES)
  • FIG. 2 ALKYL GROUPS 0 (AS SULFATES) LC /Q 23/32 v c ALKYL V c ALKYL GROUPS GROUPS AS SULFATES) (AS SULFATES)
  • FIG. 2 ALKYL GROUPS 0 (AS SULFATES) LC /Q 23/32 v c ALKYL V c ALKYL GROUPS GROUPS AS SULFATES) (AS SULFATES)
  • FIG. 2 ALKYL GROUPS 0 (AS SULFATES) LC /Q 23/32 v c ALKYL V c ALKYL GROUPS GROUPS AS SULFATES
  • sulfates are useful per se and in formulations with other adjuvants with or without other detergent active materials such as tertiary amine oxides, alkyl benzene sulfonates, linear alkyl benzene sulfonates, fatty acid ethanol amides, and fatty acid diethanol amides.
  • the invention relates to compositions of alkyl sulfate and alkyl alkoxy sulfate detergents of the formula where R is an alkyl group having from about 10 to about 20 carbon atoms; R is or mixtures; x is a number from 0 to about 6, averaging about 2-4; Me is selected from the group consisting of water soluble salt cations such as ammonium, lower alkanol ammonium and alkali metal cations.
  • alkyl sulfates and alkyl alkoxy sulfates are well known as having useful detergent properties.
  • the alkoxy groups are ethoxy
  • the detergents are abbreviated AES (alcohol ethoxy sulfates).
  • R is dodecyl
  • OR is and Me is ammonium
  • the compound is Z-dodecyloxydiethoxyethyl ammonium sulfate.
  • the typical prior art indicates a prefence for alkyl ethoxy sulfate detergents whose alkyl groups are based on mid-cut coconut alcohols which typically contain 2 percent decyl, 66 percent dodecyl, 23 percent tetradecyl, and 9 percent hexadecyl alkyl groups.
  • the emphasis upon the dodecyl preference in the prior art is stated specifically andis also indicated by the general composition requirement that at least 50 percent of the alkyl groups of the alkyl ethoxy sulfate detergents be dodecyl groups.
  • compositions which are mixtures of alkyl sulfates and alkyl alkoxy sulfates of the formula:
  • R is an alkyl group having from about 10 to about 20 carbon atoms
  • R is x is a number from O to about 6, averaging about 2-4
  • Me is lower alkanol ammonium and alkali metal.
  • Typical lower alkanol amonium cations are ethanol ammonium, diethanol ammonium and triethanol ammonium cations.
  • Typical alkali metal cations are sodium and potassium. Said mixtures are characterized in that from about 10 to about 50 percent of the R alkyl groups are decyl.
  • Preferred sulfate compositions in accordance with the foregoing are those wherein the R alkyl groups are predominantly straight chain alkyl groups; that is, where molecules with branched chain R alkyl groups constitute no more than about 20 to 25 percent of the R alkyl groups present.
  • compositions are those wherein the branched alkyl groups constitute no more than about 5 percent of the R alkyl groups present.
  • a source of such is alcohols produced by the hydrolysis of aluminum alkoxides derived from the chain growth of ethylene on a lower alkyl aluminum compound as described in US. Pat. 3,415,861.
  • compositions are those wherein the alkoxy radicals are ethoxy because of the ready avaliability and low cost of ethylene oxide and the reactivity thereof with alcohols obtained as discused in the preceding paragraph to produce ethoxylated alcohols.
  • preferred mixtures of alkyl alkoxy sulfates contain the preceding highly preferred straight chain R alkyl groups of 10-16 carbon atoms per group wherein the branched chain R alkyl groups are in tow categories, a first category being those having more than 12 carbon atoms per group and which are limited to a maximum of about 4 percent and a second category wherein the compositions contain from about 2 to about 25 percent of branched primary R alkyl groups having 12 carbon atoms per group.
  • Typical branched primary R alkyl groups are 2-ethyl decyl-, 2-butyl octyl-, 2-methyl undecyland 2-methyl dodecyl-.
  • the first is preferred for ease of production and low cost.
  • mixtures are those which contain about percent or more of sulfate molecules of straight chain carbon-oxygen skeletal configuration; that is molecules whose alkyl alkoxy radicals R(OR) are 2-decyloxyethyl, Z-undecyloxyethyl, Z-dodecyloxyethyl, Z-tridecyloxyethyl, Z-tetradecyloxyethyl,
  • mixtures which contain about 95 percent or more of straight chain R alkyl radicals having only even numbers of carbon atoms.
  • a preferred range for the percentage of decyl R alkyl groups in mixtures according to the present invention is from about 15 to about 40 percent. Such mixtures have the superior hard water performance discussed in the foregoing and additionally provide excellent performance over a wide range of hardnes of water, including soft water. Furthermore, mixtures containing tetradecyl R alkyl groups and hexadecyl R alkyl groups as essentially the only R alkyl groups in addition to decyl and dodecyl in ratios from about 1:1 to about 5:1 of tetradecyl to hexadecyl exhibit nearly uniform excellent washing effectiveness down to zero content of dodecyl R groups in the mixtures.
  • the total of decyl and dodecyl R alkyl groups is from about to about 65 percent, with the minimum percentage of decyl being about 10 percent and the minimum percentage for dodecyl R alkyl groups being about zero.
  • Typical preferred percentages of decyl R alkyl groups are 10 percent, 25 percent and 33% percent.
  • the number of alkylene oxide units in the preferred alkyl sulfates and alkyl ethoxy sulfates generally ranges from 0 for the alkyl sulfates up to about 6 ethylene oxide groups per molecule, with an average in given mixtures of about 2-4, preferably 3.
  • An average of about 3 imparts a desired emulsification capability and a characteristic of mildness to the skin; however, molecules having more than about 3 ethylene oxide units are generally inferior in sudsing ability and may detract from the performance of mixtures, hence are less desired than those of about 2-4 ethylene oxide units per molecule.
  • the cations of the alkyl sulfates and alkyl alkoxy sulfates of the present invention are selected from a group which has the property of imparting a desired degree of water solubility to the resulting salts.
  • Excellent cations for most instances are ammonium and alkanol ammonium radicals, and alkali metals, particularly sodium and potassium.
  • the ammonium radical is most preferred because of solubility of the active in liquid dishwashing formulations.
  • sodium is usually preferred because 9f the 9 efiectivefless and of the ease of reaction of low cost NaOH with sulfuric acids produced from ethoxylated alcohols by reaction with chlorosulfonic acid. Potassium is similar to sodium.
  • Typical organic base cations are alkanol ammonium cations such as ethanol ammonium, diethanol ammonium and triethanol ammonium. All of these are useful, some being preferred in various circumstances.
  • compositions are prepared in numerous ways individually and in various mixtures.
  • the components may be prepared as individual compounds or mixtures of some or all of the compounds that go to make up a final composition and blended as necessary to form the compositions claimed.
  • a particularly preferred process for producing the compositions employs as a starting feed retctant a mixture of synthetic or natural source primary alkanols ROH whose alkyl radicals R have a desired structural configuration and percentage distribution as set forth in the foregoing.
  • synthetic aluminum chemistry derived alcohols that have been treated to remove contaminants in accordance with processes of U.S. Pat. 3,468,965.
  • This selected mixture of alcohols is then reacted with a lower alkylene oxide having from 2 to about 6 carbon atoms per molecule such as ethylene oxide or propylene oxide, pure or in mixtures in the desired molar proportions, generally typically about 3 molecules of alkylene oxide such as ethylene oxide per R alkyl radical in the starting alcohols to provide a desired average of 3 ethylene oxide units per molecule of ethoxylated alcohol intermediate product.
  • a lower alkylene oxide having from 2 to about 6 carbon atoms per molecule
  • ethylene oxide or propylene oxide pure or in mixtures in the desired molar proportions
  • a greater or lesser ratio of molecules of alkylene oxide is reacted per molecule of starting alcohol; for example, a lower average of 2.5 molecules of ethylene oxide per R alkyl group or a higher average of 3.5 mols of ethylene oxide per R alkyl group of the alcohol.
  • the step of reaction of alcohols with the alkylene oxide is omitted.
  • the alcohols or alkoxylated alcohols are converted to the acid sulfate typically by reaction with chlorosulfonic acid or sulfur trioxide in accordance with well known processes such as U.S. Pat. 2,187,244.
  • acid sulfate from the preceding paragraph is reacted with an appropriate compound containing the desired cations or their precursors.
  • the acid sulfates are reacted with ammonium hydroxide in approximately 1:1 molar proportions using an aqueous solution of about 1020 percent by weight ammonium hydroxide. This produces the water soluble salts with ammonium cations.
  • the acid sulfates are reacted with sodium hydroxide in approximately 1:1 molar proportions using an aqueous solution of about 5-10 percent by weight sodium hydroxide.
  • Similar salts with potassium cations are produced by reaction with potassium hydroxide.
  • Other alkali metal salts may be produced by similar procedures.
  • Typical alkyl sulfates and alkyl alkoxy sulfates decyl ammonium sulfate dodecyl ammonium sulfate tetradecyl ammonium sulfate hexadecyl ammonium sulfate 2-decyloxyethyl ammonium sulfate 2-dodecyloxyethyl ammonium sulfate Z-tetradecyloxyethyl ammonium sulfate 2-hexadecyloxyethyl ammonium sulfate Z-decyloxyethoxyethyl ammonium sulfate 2-dodecyloxyethoxyethyl ammonium sulfate 2-tetradecyloxyethoxyethyl ammonium sulfate Z-hexadecyloxyethyl ammonium sulfate 2-decyloxy
  • a particularly effective combination of active detergent compounds includes the ammonium salt form of the present alkyl sulfates and alkyl alkoxy sulfates plus amine oxide detergents.
  • Such combinations of detergent actives are employed in conjunction with various adjuvant materials such as those set forth in the foregoing or with various adjuvants specific to desired applications such as carboxymethyl cellulose, optical brighteners, corrosion inhibitors, alkaline builders, and the like.
  • the amine oxide detergents preferred include tertiary amine oxide detergents, particularly those with two short and one long chain alkyl R, oxy alkyl R(OR') or hydroxy alkyl groups R"(CH(OH) (CH bonded to the nitrogen atom.
  • R, R and x are as heretofore defined and R" plus x plus it is equal to the number of carbon atoms in R.
  • Amine oxides having one long chain alkyl group containing for each nitrogen atom from about 10 to about 20 carbon atoms and two short chain alkyl groups containing from about 1 to about 4 carbon atoms per group are particularly preferred because of good effectiveness and low cost.
  • amine oxide detergents are dimethyl dodecyl amine oxide, dimethyl tetradecyl amine oxide and dimethyl hexadecyl amine oxide, pure and in various mixtures.
  • Such compounds are described in US. Pat. 3,001,945.
  • a mixture based on center cut coconut oil derived natural source long chain alcohols is coconut dimethyl amine oxide.
  • Such mixtures of dimethyl tertiary mono amine oxides are molecules with various long alkyl chains with a usual distribution of about 2 percent C 66 percent C 23 percent C and 9 percent C
  • Such amine oxides are described in US. Pat. 3,086,943 as are compositions based on whole coconut fatty acids.
  • Typical hydroxy amine oxides are described in US. Pat. 3,202,714 as including bis(2-hydroxy ethyl) dodecyl amine oxide, bis(2-hydroxyethyl)-2-hydroxy tetradecyl amine oxide, and the like.
  • typical tertiary amine oxides include those wherein the long radical contains ether linkages and hydroxy groups such as 1-stearoxy-2-hydroxy-3-dimethyl amino propane-N-oxide according to US. Pat. 3,499,930.
  • Other typical tertiary amine oxides include compounds containing ether linkages (oxy alkyl) in either or both short radicals with or without the ramification of ether linkages or hydroxyl groups in the long chain radical. Such are shown in British Pat. 1,053,278.
  • amine oxides are the poly amine oxides such as N,N-dimethyl-1,1-dihydrogen perfluoro octyl amine oxides and related compounds described in US. Pat. 3,194,- 767.
  • amine oxide compounds include amine oxides wherein the short chain aliphatic groups are ethyl, propyl or butyl or are mono nuclear aromatic groups or which together form heterocyclic structures as described in US. Pats. 3,317,430 and 3,324,183. Such materials are exemplified by N-benzyl-N'-methyl dodecyl amine oxide, by the mono dodecyl ether of diethanol amine oxide,
  • diamine dioxide compounds such as described in US. Pat. 3,234,139. Such compounds are exemplified as N,N-trimethyl-n-decyl trimethylene diamine-N,N'-dioxide and N,N',N-triethyl-n-dodecyl ethylene diamine-N,N'-dioxide.
  • useful light duty liquid dishwashing concentrates are produced.
  • Such concentrates contain generally from about 3 to about 10 parts by weight of the alkyl sulfate or alkyl alkoxy sulfate detergents per part of amine oxide.
  • a preferred narrower range is from about 7 to about 3 parts of said sulfates per part of amine oxide with a ratio of about :1 being most highly preferred.
  • the weight of amine oxide used is generally inversely proportional to the number of nitrogen atoms in the molecule.
  • the foregoing ratios may be advantageously doubled.
  • alkyl sulfate and alkyl alkoxy sulfate detergents of the present invention are of value is in admixture with alkyl benzene sulfonate detergents (ABS or LAS) and fatty acid mono or diethanol amides.
  • alkyl benzene sulfonate detergents ABS or LAS
  • LAS linear alkyl benzene sulfonates
  • Such LAS detergents are generally preferred types of ABS detergents because of biodegradability properties.
  • Typical LAS compounds useful in the present formulations include dodecyl benzene sodium sulfonate, undecyl benzene ammonium sulfonate, and tridecyl benzene potassium sulfonate. Included as typical are both the low and the high Z-phenyl isomers.
  • a typical ABS detergent is tetrapropylenebenzene sodium sulfonate.
  • Typical fatty acid ethanol amides are center cut coconut acid monoethanol amide, whole cut coconut acid 'diethanol amide, lauric acid diethanol amide, myristic acid monoethanol amide, palmitic acid diethanol amide, capric acid monoethanol amide.
  • ternary detergent active mixtures of: (1) alkyl benzene sulfonate detergents, (2) fatty acid mono or diethanol amide detergents and (3) the present alkyl sulfates or alkyl ethoxy sulfates, the weight proportions used range from about 3 to about 10 parts of ABS per part of aimde, and from about 2 to about 10 parts of the present sulfates per part of amide. This is expressed as: 10- 3:1:10-2. Typical proportions are 10:1:2, 10:1:3, 3:1:2, 321:3, 5:1:3, and 6:1:3, said proportions so expressed being of the components 1, 2 and 3, respectively.
  • the preferred weight ratio of ABS relative to the present sulfates in such mixtures is from about 1:1 to about 3:1 while the preferred weight ratio of the sum of the ABS and the present sulfates relative to the amide is from about 5:1 to about 10:1.
  • FIG. 1 is a plot of dishwashing performance as a function of the amount of decyl sulfates (including decylalkoxy sulfates) in typical sulfate mixtures, the balance of which typically consist essentially of dodecyl, tetradecyl and hexadecyl sulfates wherein the ratio of ethoxy units to alkyl units is an average of about 3:1 as obtained from ethoxylating alcohols with about 3 mols of ethylene oxide per mol of alcohol.
  • the data are based on experimentation wherein the proportions of the components were based on wt.
  • the information presented by FIG. 1 was derived in accordance with the Miniplate dishwashing tests described in detail hereinafter in the examples. Active matter concentration was 0.45 gram per liter at a temperature of about F.
  • Comparative dishwashing performance is shown ranging from about 40 to about 90 percent against a standard commercial dishwashing detergent to facilitate reproducibility of results over a prolonged period of testing.
  • the two curves of FIG. 1 show the performance in soft water of 0 part per million hardness, Curve A, and the performance in water of p.p.m. hardness, Curve B. Data for other hardness amounts are not plotted in FIG. 1; however, in general, the curves for hardness down to as low as 50 p.p.m. lie intermediate Curves A and B, close to and approximating the general shape of Curve B.
  • Curve B shows the superiority of present sulfate compositions containing from about 10 percent to about 50 percent decyl alkyl groups (about 8 percent to about 42 percent on the basis of the curves). It is noteworthy that a significant drop in performance is shown where the percentage of decyl alkyl groups is below about 10 percent (about 8 percent on the Curve B).
  • Curve A shows that the high percentages of decyl are less effective with soft water than with hard water providing a basis for the preferred upper limit of about 40 percent for the amount of decyl alkyl groups present in the mixtures (about 32 on the basis of the curves). It is believed evident from the Curves A and B that within the region of from about 15 to about 35 percent decyl akyl groups, (about 12.5 to 29 on the curves) high performance is obtained with soft water as well as with hard water.
  • dishwashing performance data shown in FIG. 1 are on a comparative basis and do not necessarily represent an optimum with respect to composition formulations. Nevertheless, the performance, particularly that in hard water, is extremely good representing excellent preferred formulations.
  • FIG. 2 is a ternary diagram showing 70, 80, and 90 percent comparative performance lines for various proportions of dodecyl, tetradecyl, and hexadecyl alkyl groups in mixtures containing about 12 percent decyl groups.
  • the upward curvature of the performance curve in approaching the C and C base line from the pure C apex at the lower left is highly desired.
  • the straight line between the C apex and the C -C base indicates performances where the C -C ammonium sulfate ratio is 23/32 which approximates the typical center cut coconut alkyl distribution.
  • FIG. 3 is similar to FIG. 2 showing the comparative performance of detergents evaluated as discussed in connection with FIGS. 1 and 2; however, in this instance, the performance lines shown for 60, 70, 75, 80 and 85 percent are derived when using ammonium sulfates containing substantially no decyl alkyl groups.
  • the data of FIG. 3 represent the performance of ternary mixtures of dodecyl, tetradecyl and hexadecyl sulfates (3 :1 ethoxy unit average) wherein the only additional active material present is lauryl dimethylene oxide in an amount of about 1 part of a total of 6 by weight.
  • Comparative performance on the typical 23/32 ratio of C /C drops from about 84 percent for the 65 percent dodecyl ammonium sulfate composition to about 80 percent for 42 percent dodecyl ammonium sulfate composition, to about 75 percent for a dodecyl ammonium sulfate content of about 21 percent, to about 70 percent for a dodecyl ammonium sulfate content of about 19 percent and reaches an estimated 66 percent for 0 dodecyl ammonium sulfate content.
  • FIGS. 2 and 3 show that in general the effect of increased amounts of decyl alkyl groups beyond the 12 percent level of FIG. 1 will result in at least equivalent performance to that at the 12 percent C alkyl level.
  • FIG. 4 shows a plot of dishwashing performance using the compositions and procedure of Example III.
  • the dotted line shows the performance of the C1244 AES as inferior to the mixtures containing C1042 AES. Superior performance is shown by the dash and dot-dash lines with the solid line showing a limitation on the amount of C1042 present.
  • Example I A group of standard alkoxy alkyl ammonium sulfate samples were prepared from alkanols as hereinafter described and blended in various proportions to provide compositions which were tested to derive the data for FIGS. 1, 2 and 3 of the drawing and to define the limits for the compositions claimed herein.
  • Normal indicates alcohol with unbranched carbon skeleton structure having only a single hydroxyl group attached to only one terminal carbon atom.
  • Branched alcohols are similar to the normal alcohols with the exception of having one hydrogen atom on the second carbon atom of the carbon skeleton substituted by a short chain alkyl group such as methyl, ethyl, propyl or butyl. In the particular alcohols chosen the substitution consists essentially of ethyl and butyl groups, with ethyl predominating at least about 3: 1.
  • Fatty alcohols used had the following compositions:
  • the four alcohol mixtures were individually reacted with ethylene oxide using sodium hydroxide as a catalyst to give an alcohol polyoxyethylene containing an average of 3 moles of ethylene oxide.
  • the ethylene oxide adducts were analyzed according to a procedure described in J. Am. Oil Chem. Soc., 46, 289 (1969).
  • the alcohol ethoxylates were sulfated with sulfamic acid in trichlorofiuoromethane using a urea catalyst.
  • molar ratio of alcohol ethoxylate to sulfamic acid was 1:1.05. About 0.13 g. of urea per one gram of sulfamic acid was used as a catalyst.
  • the reactants Were heated in an autoclave to 120 C. and this temperature was maintained for 30 minutes before cooling the reactor with an ice-water mixture.
  • the pH of the mixture was adjusted to 9.5 with ammonia and then the mixture was filtered with the aid of Filter Aid.
  • the filtrate was evaporated to leave a solid ammonium alcohol ethoxy sulfate which was dissolved in a mixture of percent ethanol and water. This solution was deoiled with petroleum ether (B.P. 36-57 C.).
  • the oil content of the final product was about 0.2-0.5 percent (58 percent active basis) (Analytical Method described in ASTM Standards, Part 22, D1570-63, 1968). The concentration of alcohol ethoxy sulfates was determined by cationic titration procedure (ASTM Standards, Part 22, D1681-62, 1968).
  • the alcohol ethoxy sulfates were also prepared from the alcohol ethoxylate and chlorosulfonic acid.
  • the alcohol ethoxylate and chlorosulfonic acid (1:1.03 ratio) were reacted in trichlorofluoro methane in a glass reaction vessel fitted with a stirrer, Dry Ice condenser and addition funnels blanketed with nitrogen.
  • the chlorosulfonic was added at such a rate as to maintain a moderate reflux. When the addition was complete, the mixture was refluxed for about one hour. Solvent and dissolved HCl were then evaporated.
  • the resulting acid sulfate was neutralized with about 20 percent ammonium hydroxide solution. Ethanol was added to increase solubility.
  • the neutralized product was deoiled and analyzed as described above.
  • Lauryl dimethylamine oxide 17 Performance of various combinations of Claims with 10 percent C AES (12 percent C alkyl group content) at 150 p.p.m. water hardness as a percent of the commercial standard are shown in FIG. 1. Synergism of C AES is seen when comparing similar performance without C10 i.e., percent 3 4 AES B, C, D and percent lauryl dimethylamine oxide (see FIG. 2). A similar synergistic effect was observed with C ABS at 50 and 300 p.p.m. water hardness.
  • Example II The following alkanol mixture was ethoxylated, sulfated and neutralized with ammonium hydroxide according to procedures outlined in Example I.
  • the branched alcohols consisted essentially of 2-ethyl and 2-butyl branched alcohols.
  • the Dynamic Foam Dishwashing Test was used (J. Am. Oil Chem. Soc. 31 (1954)). Active concentration was 0.2 wt. percent. Added increments of soil of 0.125 gram were used in place of 0.1 gram as described in the reference. The C1244 ethoxy sulfate was replaced with up to 40 percent of the C1042 ethoxy sulfate.
  • the dishwashing results at 150 p.p.m. water hardness are shown in FIG. 4. The beneficial effect of C alcohol ethoxy sulfate on dishwashing performance is shown by this data. Improved performance due to C AES was also observed at 25, 50 and 300 p.p.m. water hardness.
  • Weight percent ethoxy sulfates Composition Example IV Preceding examples are repeated with other compositions of sulfates and ethoxy sulfates described in the foregoing. Similar desirable results are obtained. Those materials under test include alkanol ammonium and alkali metal sulfates such as the ethanol ammonium, diethanol ammonium, triethanol ammonium, sodium and potassium sulfates described. Other tests employ various numbers of alkoxy units of the identity and ratio per molecule herein defined. Proportions covered include the ranges set forth in the appended claims for compositions and formulations of those compositions with other detergent actives and adjuvants discussed herein.
  • composition of claim 1 wherein from about 15 to about 40 percent of the alkyl groups are decyl.
  • composition of claim 1 wherein the average number of ethoxy groups present is about three per molecule.
  • composition of claim 1 wherein from about 15 to about 40 percent of the alkyl groups are decyl, wherein the average number of ethoxy groups present is about tlgfee per molecule, and Where the sulfates are ammonium s ts.
  • composition of claim 1 wherein about 25 percent of the alkyl groups are decyl.
  • composition of claim 1 wherein about one-third of the alkyl groups are decyl.
  • composition of claim 1 wherein the sulfates are ammonium salts.
  • composition of claim 1 wherein the sulfates are ethanolammonium, diethanolammonium, or triethanolammonium salts.
  • composition of claim 1 wherein the sulfates are alkali metal salts.
  • composition of claim 1 wherein the sulfates are sodium salts.
  • composition of claim 1 wherein the total of decyl and dodecyl alkyl groups is from about 10 to about 65 percent and wherein the minimum percentage of decyl alkyl groups is about 10 percent, the balance up to percent consisting essentially of tetradecyl and hexadecyl alkyl groups in ratios of tetradecyl to hexadecyl from about 1:1 to about 5:1.
  • a light-duty detergent composition consisting essentially of alkyl benzene sulfonate detergent, fatty acid mono or diethanol amide and alkyl ethoxy sulfates as defined in claim 1, the proportions ranging from about 3 to about 10 parts by weight of alkyl benzene sulfonate detergent per part of fatty acid mono or diethanol amide, and from about 2 to about 10 parts by weight of said sulfates per part of fatty acid mono or diethanol amide.
  • a composition in accordance with claim 12 wherein the weight ratio of the alkyl benzene sulfonate detergent relative to said sulfates is from about 1:1 to about 3:1 and wherein the weight ratio of the sum of the alkyl benzene sulfonate detergent and the said sulfates relative to the amide is from about 5:l to about 10:1.
  • a light duty detergent composition consisting essentially of: (a) alkoxy ethoxy sulfates as defined in claim 1, and (b) tertiary amine oxide detergent having two short and one long chain alkyl R, oxy alkyl R('OR),, or hydroxy alkyl groups R"(CI-I(OH) ),,(C3H bonded to the nitrogen atom wherein R is an alkyl group having from about 10 to about 20 carbon atoms; R is -cH,cH,) or (-H-CH: or mixtures; x is a number from to about 6, averaging about 2-4, R"+x+n is equal to the number of carbon atoms in R, the proportions on a weight basis ranging from about parts of said sulfates per part of amine oxide to about 3 parts of said sulfates per part of amine oxide.
  • composition of claim wherein the weight ratio of said sulfates per part of amine oxide detergent is from about 7 to 1 to about 3 to l.
  • composition of claim 15 wherein the tertiary amine oxide detergent contains one long chain and two short chain alkyl, oxy alkyl or hydroxy alkyl groups, the long chain group having from about 10 to about carbon atoms, the short chain groups having from 1 to about 4 carbon atoms.
  • composition of claim 15 wherein the amine oxide detergent has one long chain alkyl group containing from about 10 to about 20 carbon atoms and two short chain alkyl groups containing from about 1 to about 4 carbon atoms.
  • composition of claim 15 wherein the tertiary amine oxide detergent contains one long chain alkyl group having from about 10 to about 20 carbon atoms and two methyl groups.
  • composition of claim 15 wherein the tertiary amine oxide detergent contains one long chain alkyl group having from about 10 to about 16 carbon atoms and two methyl groups.
  • composition of claim 15 wherein the tertiary amine oxide detergent is dimethyl decyl amine oxide, dimethyl undecyl amine oxide, dimethyl dodecyl amine oxide, dimethyl tridecyl amine oxide, dimethyl tetradecyl amine oxide, dimethyl pentadecyl amine oxide or dimethyl hexadecyl amine oxide, and mixtures thereof.
  • FIG. '3 5 line 5 reads "FIG. 5"
  • FIG. 2 The le end "0 /0l 25/52" at the right hand side of the Figure should read O /C 25/9 FIG. 5.

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Cited By (30)

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US3898186A (en) * 1973-04-09 1975-08-05 Procter & Gamble Dishwashing compositions containing gel forming gelatin
US3979340A (en) * 1973-04-09 1976-09-07 Colgate-Palmolive Company Olefin sulfonate detergent compositions
US4024078A (en) * 1975-03-31 1977-05-17 The Procter & Gamble Company Liquid detergent composition
US4028280A (en) * 1975-09-04 1977-06-07 Kao Soap Co., Ltd. Non-phosphate or reduced phosphate detergent compositions containing mixtures of alkyl ether sulfates
US4132678A (en) * 1975-09-16 1979-01-02 Kao Soap Co., Ltd. Transparent liquid shampoo
US4144201A (en) * 1976-11-05 1979-03-13 Lever Brothers Company Liquid detergent compositions having improved drain-dry and mildness properties
US4188311A (en) * 1975-07-24 1980-02-12 Chem-Y, Fabriek Van Chemische Produkten B.V. Detergent compositions containing ether sulfates
US4285356A (en) * 1979-10-12 1981-08-25 Conoco, Inc. Method of transporting viscous hydrocarbons
US4316824A (en) * 1980-06-26 1982-02-23 The Procter & Gamble Company Liquid detergent composition containing alkyl sulfate and alkyl ethoxylated sulfate
US4395364A (en) * 1979-11-16 1983-07-26 Kao Soap Co., Ltd. Detergent composition containing sulfonate surfactant and polyoxyalkylene alkyl or alkenyl sulfuric acid ester salt
US4592875A (en) * 1984-06-25 1986-06-03 Atlantic Richfield Company Alkoxylated ether sulfate anionic surfactants from plasticizer alcohol mixtures
US4594185A (en) * 1984-06-25 1986-06-10 Atlantic Richfield Company Alkoxylated plasticizer alcohol ether sulfate surfactants
US4608197A (en) * 1984-06-25 1986-08-26 Atlantic Richfield Company Alkoxylated ether sulfate anionic surfactants from branched chain plasticizer alcohols
US4731201A (en) * 1986-08-12 1988-03-15 Colgate-Palmolive Company Shampoo method and composition
US4997641A (en) * 1990-04-09 1991-03-05 Colgate-Palmolive Company Hair conditioning shampoo containing C6 -C10 alkyl sulfate or alkyl alkoxy sulfate
WO1996006149A1 (en) * 1994-08-23 1996-02-29 The Procter & Gamble Company Detergent compositions
US5854196A (en) * 1994-08-23 1998-12-29 The Procter & Gamble Company Detergent compositions
US6008181A (en) * 1996-04-16 1999-12-28 The Procter & Gamble Company Mid-Chain branched Alkoxylated Sulfate Surfactants
US6015781A (en) * 1996-04-16 2000-01-18 The Procter & Gamble Company Detergent compositions containing selected mid-chain branched surfactants
US6020303A (en) * 1996-04-16 2000-02-01 The Procter & Gamble Company Mid-chain branched surfactants
US6046152A (en) * 1996-04-16 2000-04-04 The Procter & Gamble Company Liquid cleaning compositions containing selected mid-chain branched surfactants
US6060443A (en) * 1996-04-16 2000-05-09 The Procter & Gamble Company Mid-chain branched alkyl sulfate surfactants
US6099589A (en) * 1997-12-30 2000-08-08 Kay Chemical Company Presoak detergent with optical brightener
US6228829B1 (en) 1997-10-14 2001-05-08 The Procter & Gamble Company Granular detergent compositions comprising mid-chain branched surfactants
US6281181B1 (en) 1997-10-14 2001-08-28 The Procter & Gamble Company Light-duty liquid or gel dishwashing detergent compositions comprising mid-chain branched surfactants
US6335312B1 (en) 1997-10-14 2002-01-01 The Procter & Gamble Company Personal cleansing compositions comprising mid-chain branched surfactants
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NZ206213A (en) * 1982-11-16 1985-12-13 Unilever Plc Foaming liquid detergent compositions containing alkylbenzenesulphonates and alkyl ether sulphates
DE3839016A1 (de) * 1988-11-18 1990-05-23 Henkel Kgaa Wasch- und reinigungsmittel mit einem gehalt an sek. dialkylethersulfaten
JPH03129348U (nl) * 1990-04-10 1991-12-26
GB2290301B (en) * 1994-05-31 1998-09-02 Mcbride Robert Ltd Detergent formulation

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Publication number Priority date Publication date Assignee Title
US3979340A (en) * 1973-04-09 1976-09-07 Colgate-Palmolive Company Olefin sulfonate detergent compositions
US3898186A (en) * 1973-04-09 1975-08-05 Procter & Gamble Dishwashing compositions containing gel forming gelatin
US4024078A (en) * 1975-03-31 1977-05-17 The Procter & Gamble Company Liquid detergent composition
US4188311A (en) * 1975-07-24 1980-02-12 Chem-Y, Fabriek Van Chemische Produkten B.V. Detergent compositions containing ether sulfates
US4028280A (en) * 1975-09-04 1977-06-07 Kao Soap Co., Ltd. Non-phosphate or reduced phosphate detergent compositions containing mixtures of alkyl ether sulfates
US4132678A (en) * 1975-09-16 1979-01-02 Kao Soap Co., Ltd. Transparent liquid shampoo
US4144201A (en) * 1976-11-05 1979-03-13 Lever Brothers Company Liquid detergent compositions having improved drain-dry and mildness properties
US4285356A (en) * 1979-10-12 1981-08-25 Conoco, Inc. Method of transporting viscous hydrocarbons
US4395364A (en) * 1979-11-16 1983-07-26 Kao Soap Co., Ltd. Detergent composition containing sulfonate surfactant and polyoxyalkylene alkyl or alkenyl sulfuric acid ester salt
US4316824A (en) * 1980-06-26 1982-02-23 The Procter & Gamble Company Liquid detergent composition containing alkyl sulfate and alkyl ethoxylated sulfate
US4592875A (en) * 1984-06-25 1986-06-03 Atlantic Richfield Company Alkoxylated ether sulfate anionic surfactants from plasticizer alcohol mixtures
US4594185A (en) * 1984-06-25 1986-06-10 Atlantic Richfield Company Alkoxylated plasticizer alcohol ether sulfate surfactants
US4608197A (en) * 1984-06-25 1986-08-26 Atlantic Richfield Company Alkoxylated ether sulfate anionic surfactants from branched chain plasticizer alcohols
US4731201A (en) * 1986-08-12 1988-03-15 Colgate-Palmolive Company Shampoo method and composition
AU601996B2 (en) * 1986-08-12 1990-09-27 Colgate-Palmolive Company, The Shampoo method and composition
US4997641A (en) * 1990-04-09 1991-03-05 Colgate-Palmolive Company Hair conditioning shampoo containing C6 -C10 alkyl sulfate or alkyl alkoxy sulfate
WO1996006149A1 (en) * 1994-08-23 1996-02-29 The Procter & Gamble Company Detergent compositions
US5854196A (en) * 1994-08-23 1998-12-29 The Procter & Gamble Company Detergent compositions
US6020303A (en) * 1996-04-16 2000-02-01 The Procter & Gamble Company Mid-chain branched surfactants
US6008181A (en) * 1996-04-16 1999-12-28 The Procter & Gamble Company Mid-Chain branched Alkoxylated Sulfate Surfactants
US6046152A (en) * 1996-04-16 2000-04-04 The Procter & Gamble Company Liquid cleaning compositions containing selected mid-chain branched surfactants
US6060443A (en) * 1996-04-16 2000-05-09 The Procter & Gamble Company Mid-chain branched alkyl sulfate surfactants
US6087309A (en) * 1996-04-16 2000-07-11 The Procter & Gamble Company Liquid cleaning compositions containing selected mid-chain branched surfactants
US6015781A (en) * 1996-04-16 2000-01-18 The Procter & Gamble Company Detergent compositions containing selected mid-chain branched surfactants
US6133222A (en) * 1996-04-16 2000-10-17 The Procter & Gamble Company Detergent compositions containing selected mid-chain branched surfactants
US6326348B1 (en) 1996-04-16 2001-12-04 The Procter & Gamble Co. Detergent compositions containing selected mid-chain branched surfactants
US6335312B1 (en) 1997-10-14 2002-01-01 The Procter & Gamble Company Personal cleansing compositions comprising mid-chain branched surfactants
US6228829B1 (en) 1997-10-14 2001-05-08 The Procter & Gamble Company Granular detergent compositions comprising mid-chain branched surfactants
US6281181B1 (en) 1997-10-14 2001-08-28 The Procter & Gamble Company Light-duty liquid or gel dishwashing detergent compositions comprising mid-chain branched surfactants
US6099589A (en) * 1997-12-30 2000-08-08 Kay Chemical Company Presoak detergent with optical brightener
WO2014135606A1 (de) * 2013-03-05 2014-09-12 Attratec Gmbh Neue formulierungshilfstoffe, deren herstellung und verwendung
CN105188368A (zh) * 2013-03-05 2015-12-23 拜耳知识产权有限责任公司 新型制剂助剂及其制备和用途
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US10091994B2 (en) 2013-03-05 2018-10-09 Bayer Intellectual Property Gmbh Formulation additives, production and use thereof
CN107207951A (zh) * 2014-12-26 2017-09-26 丰田自动车株式会社 冷却剂组合物、使用其操作内燃机的方法及其用途
US10160895B2 (en) * 2014-12-26 2018-12-25 Toyota Jidosha Kabushiki Kaisha Coolant composition, method of operating internal combustion engine using the same, and use of the same
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US10087403B2 (en) 2017-01-11 2018-10-02 The Procter & Gamble Company Detergent compositions having surfactant systems
US10696931B2 (en) 2017-01-11 2020-06-30 The Procter & Gamble Company Detergent compositions having surfactant systems
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US10731107B2 (en) 2017-06-30 2020-08-04 The Procter & Gamble Company Detergent compositions comprising AES surfactant having alkyl chain lengths of fourteen total carbons

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GB1349554A (en) 1974-04-03
DE2132300A1 (de) 1972-01-05
DE2132300B2 (de) 1979-06-07
DE2132300C3 (nl) 1980-01-31
JPS5017204B1 (nl) 1975-06-19
FR2100009A5 (nl) 1972-03-17
NL7108926A (nl) 1971-12-31

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