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
  • C11D1/66—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
  • C11D1/37—Mixtures of compounds all of which are anionic
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/34—Organic compounds containing sulfur
  • C11D3/3409—Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates

Definitions

• Typical systems may include in addition to the olefin sulfonate and the hydroxyalkane sulfonic acid salt, other detergent actives such as alkyl ether sulfates, tertiary amine oxides, amides, ethanol amides and other conventional detergent actives and adjuvants.
• other detergent actives such as alkyl ether sulfates, tertiary amine oxides, amides, ethanol amides and other conventional detergent actives and adjuvants.
• This invention relates to liquid detergent compositions containing olefin sulfonates in aqueous systems and is directed to the avoidance of the gel formation problem characteristic of aqueous systems containing ole-fin sulfonates.
• the gel formation problem is avoided or materially reduced by using in such aqueous olefin sulfonate systems a soluble salt of a hydroxy-alkane sulfonic acid and in particular one wherein the hydroxy group is an omega hydroxy group and wherein the alkane structure contains form 2 to about 6 carbon atoms.
• olefin sulfonates have been characterized by unlikely acceptance because of difficulty of use in the conventional manner familiar to the housewife.
• an olefin sulfonate based detergent from biodegradability and cost-effectiveness viewpoints, such cannot be used if it cannot be removed from the container in an easy and conventional manner.
• the bottle-cap dispenser is an example of a widelyused type of dispenser that is prone to pluggage due to the formation of gels with olefin sulfonates.
• this dispenser usually contains a simple arrangement of a flow passage having a diameter of from several millimeters up to about 10 or 20 millimeters, typically millimeters. The small diameter and exposed position relative to air provides a particularly adverse combination of conditions prone to gellation.
• Olefin sulfonate detergents are generally used as formulations containing other detergent materials.
• the olefin sulfonates may be used in formulations containing only one of the aforementioned AES, amine oxide or amide materials, a particularly preferred formulation is a formulation which contains both ABS and amides or both ABS and amine oxide together with the olefin sulfonates.
• n is 1 to 6, preferably 1 or 2 particularly 1; and M is an alkali metal, ammonium or ethanol ammonium cation.
• the amount of anti-gelling compound useful for the anti-gelling capability ranges from about 1 to about 15 percent by weight of the liquid detergent formulation.
• a preferred range is from about 3 to about 10 percent by weight, about 5 percent by weight being particularly preferred.
• the ratio of detergent actives relative to the HOCH (CH ),,SO M is from about 2:1 to about 30:1.
• a particularly preferred anti-gelling additive is sodium isethionate or beta hydroxyethane sulfonic acid sodium salt and which has the formula HOCH CH SO Na.
• Other typical additives include omega hydroxypropane sulfonic acid potassium salt, omega hydroxyisopropane sulfonic acid sodium salt, omega hydroxybutane sulfonic acid sodium salt, omega hydroxypentane sulfonic acid potassium salt, omega hydroxyhexane sulfonic acid monoethanol ammonium salt, omega hydroxybutane sulfonic acid ammonium salt, beta hydroxyethane sulfonic acid triethanol ammonium salt, omega hydroxypropane sulfonic acid diethanol ammonium salt.
• the hydroxyalkane can be produced by any suitable pror art process.
• beta hydroxyethane sulfonic acid sodium salt is described by Lauer and Hill in Journal of the American Chemical Society, vol. 58, p. 1873 (1936). This compound is produced by reacting NaHSO with ethylene oxide.
• the olefin sulfonate used is typically an alkali metal, ammonium or ethanol ammonium salt of a mixture of alkene and hydroxyalkane sulfonates having from about 12 to about 16 carbon atoms per molecule. It is obtained by reacting olefin with gaseous uncomplexed S in a ratio of about 1 mol of S0 per mol of olefin followed by a saponification with an appropriate base such as NaOH, preferably at temperatures of from about 100 to about 150 C. As disclosed in U.S. Pat.
• olefin sulfonates are produced typically by a reaction of the olefin in a liquid S0 diluent system or in a gaseous diluent system.
• An example of the former is U.S. Pat. 2,061,617 while examples of the latter are U.S. Pats. 2,697,031 and 3,169,- 142.
• Preferred sulfonates are those which are predominantly of a structure with a sulfonate group attached to a terminal C atom.
• Sulfonates whose sulfonate group are attached to non-terminal carbon atoms such as those produced by the sulfonation of internal olefins are also desirable, particularly when such are components of mixed systems containing derivatives of vinyl, vinylidene and internal types of olefins.
• Such sulfonates are characterized as being of substantially open chain carbon skeleton structures.
• the derivatives of pure olefins may be used or may be produced separately and blended into mixtures as herein described, the sulfonation of mixtures of olefins is preferred, typically mixtures having up to about 20 percent C 2, up to about 100 percent C and up to about 80 percent C and which contain predominantly straight chain terminal olefins plus from about 3 to about 30 mol percent of beta branched terminal olefins and from about 3 to about 12 mol percent of internal olefins, the latter preferably being predominantly straight chain.
• Such preferred olefins are typically obtained by the so-called Ziegler process of chain-growth with ethylene on a lower trialkyl aluminum compound to produce a higher alkyl trialkyl aluminum as described in U.S.
• the sulfonates thus produced are essentially acyclic and contain a wide spectrum of open chain compounds in two general classes of unsaturated and hydroxyalkane compounds some of which have two or more sulfonic acid groups and which frequently are called disulfonates.
• the compounds are predominantly alkene sulfonates and hydroxyalkane sulfonates many of which are described individually or in groups in U.S. Pats.
• the alcohol ether sulfate component optionally used in compositions in accordance with the present invention is typically obtained as an aqueous system of the product of sulfntion of ethoxylated alcohols with chlorosulfonic acid.
• the alcohols ethoxylated are pure alkanols or mixtures of As mentioned also in U.S. Pat. 3,332,876, the alkyl ether prior literature, such are less preferred in connection with U.S. Pats. 3,384,651 and 3,415,861.
• the ethoxylated derivatives preferably average from about 1 to about 5 ethylene oxide units per molecule.
• the alkl ether sulfates can be made by the condensation by known methods of ethylene oxides on to monohydric alcohols from various natural or synthetic sources and having 10 to 18 carbon atoms per molecule. Molar proportions of ethylene oxide to alcohol are generally 1 to 5. The resulting ethoxylated alcohol is then sulfated and neutralized with an appropriate base such as alkali metal hydroxide, ammonium hydroxide of ethanol ammonium base.
• an appropriate base such as alkali metal hydroxide, ammonium hydroxide of ethanol ammonium base.
• the amide component used in formulation in accordance with the present invention are fatty acid amides and fatty acid monoand di-lower alkanol amides having from about 10 to about 14 carbon atoms in the fatty acid alkyl groups, particularly those having also lower alkanol groups of from 2 to 6 carbon atoms such as lauryl monoethanol amide, myristyl diethanol amide, myristyl mono isopropanol amide and lauryl diisopropanol amide.
• the alkyl groups present are preferably pure individual or mixed coconut range alkyls, typically a mixed alkyl distribution of a whole cut coconut oil or of a center cut coconut oil.
• Amine oxides suitable for use in the compositions of the present invention are conventional detergent components Whose structures and methods of preparation are well known to those skilled in the art as disclosed for example by US. Pats. 2,169,976; 3,001,945; 3,234,282; 3,317,430; 3,397,239 and by Canadian Pat. 847,303.
• Typical and preferred amine oxides are long chain dimethyl amine oxides such as lauryl dimethyl amine oxide and myristyl dimethyl amine oxide.
• R and R are lower alkyl radicals or hydroxy alkyl radicals having from 1 to about 4 carbon atoms and R is a saturated aliphatic radical having from about to about 20 carbon atoms, (3) an alkyl ether sulfate having the formula RO(C H O),,SO M, wherein R is an alkyl chain of from about 10 to about 18 carbon atoms; x is a value from 1 to about 5, the cation of said sulfonate and the cation of M of such sulfate being independently selected from the group consisting of alkali metal, ammonium and ethanol ammonium; plus (C) a hydroxyalkane sulfonate of the formula HOCH (CI-I ),,SO M', wherein n is from
• the hydroxyalkane sulfonate is beta hydroxyethane sulfonic acid, sodium salt.
• a coupling agent which preferably is a lower alkanol having up to about 6 carbon atoms per molecule.
• a preferred alkanol is ethyl alcohol.
• Other suitable alkanols include normal propyl alcohol, isopropyl alcohol, butyl alcohols, amyl alcohols, and hexyl alcohols.
• the coupling agent is used in proportions of up to about 15 percent by weight based on the composition, more preferably from about 2 to about 10 percent by weight, on the same basis.
• the mono olefin sulfonate is the product of the saponification with NaOH of the product of sulfonation of predominantly straight chain terminal olefins with uncomplexed S0,; in proportions of from about 0.9 to about 1.1 mols of S0 per mol of olefin.
• the predominantly straight chain terminal olefins used in the sulfonation contain from about 3 to about 30 percent on a mol basis of beta-branched terminal olefins and from about 3 to about 12 percent on a mol basis of internal olefins.
• the internal olefins are substantially all straight chain.
• the proportionsof Components A, B and C on a weight basis are from about 15 to about 30 percent, from about 10 to about percent, and from about 1 percent to about 10 percent, respectively.
• the proportions of Components A, B and C on a weight basis are from about 15 to about 30 percent, from about 10 to about 20 percent, and from about 1 percent to about 15 percent, respectively, and the Component B is a mixture of alkyl ether sulfate as defined in the foregoing and fatty acid monoor di-lower alkanol amide as described in the foregoing in a weight ratio of from about 4:1 to about 2:1 of alkyl ether sulfate relative to amide.
• the proportions of A, B and C on a weight basis are from about 15 to about 30 percent, from about 10 to about 20 percent, and from about 1 percent to about 10 percent, respectively, and the Component B is a mixture of alkyl ether sulfate and tertiary amine oxide in weight ratio of from about 4: l to about 2:1 of alkyl ether sulfate relative to tertiary amine oxide.
• Component A is the product of saponification with NaOH of the product of sulfonation with uncomplexed S0,, of a mixture of predominantly straight chain terminal olefins having from about 12 to about 16 carbon atoms per molecule.
• Component B is a mixture of alkyl ether sulfate and lauryl dimethylamine oxide or, alternately,
• compositions in accordance with this embodiment contain the usual proportions of other conventional detergent adjuvants and actives including perfume, dye, water softeners, etc. as described in the patents cited herein.
• Formulations of olefin sulfonates in accordance with the present invention preferably are made into aqueous systems ranging from about 50 to about 75 percent water on a weight percent basis providing a more or less thick liquid system.
• the detergent active ingredients mentioned as well as the hydroxyalkane sulfonic acid Component (C) are for the most part used in the form of solids added to water to ultimately result in a system of the desired water content.
• An exception to this is the alcohol ether sulfate which is usually obtained in an aqueous solution of about 60 wt. percent AES concentration.
• preferred compositions of the present invention are expressed broadly as 40-70' percent olefin sulfonate, 5-40 percent alcohol ether sulfate and 1-20 percent amide.
• the lower alkanol described as useful as a coupling agent typically ethanol, may be replaced wholly or partially by humectants such as propylene glycol, glycerine and sorbitol.
• the AES was Alfonic l4-12A ether sulfate manufactured by Continental Oil Company. It is based on 3 mols ethoxylate of a mixture of mainly dodecanol and tetradecanol in a 40/60 ratio by weight, as the ammonium salt.
• the lauryl dimethyl amine oxide was Aromox (Armour Industrial Chemical Co.) DMMCDW containing 1.0 percent C 70.0 percent C 24 percent C 5 percent C by weight distribution of the long chain alkyl groups.
• the monoethanol amide was Stepan Ninol AA-62 Extra.
• the beta hydroxyethane sulfonic acid, sodium salt was GAF Sodium Isethionate manufactured by General Aniline and Film Company.
• the A08 was a C /C olefin derivative.
• the A08 used was the product of saponification at C. with NaOH of the product of sulfonation with gaseous S0 in a falling-film reactor at 30 C. of olefins (Wt. percent C 0.4; C -66.2; C 33.4; average C No. 14.6, average MW 205) (mol percent by NMR vinyl79.2; vinylidene12.5; internal-8.2) produced by displacement of the product of chain growth of ethylene or triethyl aluminum.
• EXAMPLE II (C) a hydroxyalkane sulfonate of the formula:
• a quick screening test was provided for determining 2 z)n s the gelling characteristics of detergent formulations. The wherein n is from 1 to about 6, and the cation M components of the formulations were as described in Example I.
• a glass plate approximately 70 cm. in length was placed with one end thereof 17.5 centimeters higher than the other forming an inclined plane surface.
• a portion of the detergent formulation to be tested was placed upon the glass plate near the upper end and the flow characteristics that resulted were evaluated. In those instances where a smooth substantially straight downward flow along the plate was obtained, the material under test was rated as having a satisfactory performance with regard to anti-gelling, the results correlating closely with the bottle cap test.
• compositions using beta hydroxyethane sulfonic acid, sodium salt were found to produce test results indicative of suitable non-gelling properties for the sodium isethionate-containing compositions in contrast to unsatisfactory gelling properties for the similar compositions that did not contain beta hydroxyethane sulfonic acid, sodium salt.
• (D) water said composition containing from about 15 to about 60 percent by weight of A+B+C, the proportions of A to B being from about 15:1 to about 1:1 on a wt. basis and the weight ratio of A plus B to C being from about 2:1 to about 30:1.
• composition of claim 1 wherein the hydroxy alkyl sulfonate is beta hydroxyethane sulfonic acid, sodium salt.
• composition in accordance with claim 1 containing a coupling agent in proportions of up to about 15 percent by weight of the composition.
• composition of claim 3 wherein the coupling agent is ethyl alcohol.
• composition of claim 1 wherein the monoolefin sulfonate is the product of the saponification with NaOH of the product of sulfonation of predominantly straight chain terminal olefins with uncomplexed 80;, in proportions of from about 0.9 to about 1.1 mols of S0 per mol of olefin.
• a gel resistant liquid detergent composition consisting essentially of:
• A a monoolefin sulfonate having from about 12 to about 16 carbon atoms in the molecule;
• B at least one of:
• composition in accordance with claim 1 wherein the proportions of Components A, B and C on a weight basis are from about 15 to about 30 percent, from about 10 to about 20 percent, and from about 1 percent to about 15 percent, respectively and wherein the Component B is a mixture of 3 and 1 in weight ratio of from about 4:1 to about 2:1.
• composition in accordance with claim 1 wherein the proportions of Components A, B and C on a weight basis are from about 15 to about 30 percent, from about 10 to about 20 percent, and from about 1 percent to about 10 percent, respectively and wherein the Component B is a mixture of 3 and 2 in weight ratio of from about 4: 1 to about 2:1.
• Component A is the product of saponification with NaOH of the product of sulfonation with uncomp exed of a mixture of predominantly straight chain terminal olefins having from about 12 to about 16 carbon atoms per molecule
• Component B is a mixture of alkyl ether sulfate and lauryldimethyl amine oxide in a wt. ratio of about 3:1
• Component C is beta hydroxyethane sulfonic acid, sodium salt
• the proportions of Components A, B and C on a weight basis are about 21 percent, about 16 percent, and about 5 percent, respectively and wherein the system contains about 5 percent ethyl alcohol as coupling agent.
• composition in accordance with claim 1 containing a lower alaknol having up to about 6 carbon atoms per molecule in proportions of up to about 15 percent by weight of the composition.
• composition of claim 11 wherein the lower alkanol is ethyl alcohol.
• the ethoxylated derivatives preferably average from about 1 to about 5 ethylene oxide units per molecule -5 line 7, reads "alkl”, should read alkyl Column 9, line 12, reads "alaknol”, should read alkanol Signed and sealed this 12th day of November 1974.

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Cited By (18)

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• 1971
  • 1971-11-22 US US00201197A patent/US3808156A/en not_active Expired - Lifetime
• 1972
  • 1972-11-20 FR FR7241172A patent/FR2160886B1/fr not_active Expired
  • 1972-11-22 JP JP47117611A patent/JPS5023841B2/ja not_active Expired

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