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
  • C11D1/02—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
  • C11D1/38—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
  • C11D1/72—Ethers of polyoxyalkylene glycols
• • 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
  • C11D1/831—Mixtures of non-ionic with anionic compounds of sulfonates with ethers of polyoxyalkylenes without phosphates
• • 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
  • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
  • C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
• • 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
  • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
  • C11D17/0004—Non aqueous liquid compositions comprising insoluble particles

Definitions

• This invention is directed to new and useful anhydrous or essentially anhydrous liquid surfactant compositions, and more particularly to polyfunctional liquid detergent compositions that comprise essentially 100% active organic surfactants and to a method of making them.
• aqueous slurries of the alkyl aryl sulfonates are utilized and, in Example 1 of said patent, which describes a detergent composition produced in the absence of either a liquid medium or water as added diluent, a very considerable amount of water is actually present, namely, about 16% of the total composition.
• the alkyl aryl sulfonates such as dodecylbenzene sulfonate, can be utilized in the form of their alkali metal, ammonium or alkanolamine salts.
• a 100% active, or essentially 100% active, or essentially anhydrous polyfunctional organic detergent composition in the form of a clear, homogeneous, stable liquid can be prepared by a certain balancing of a number of essential ingredients, and advantageously employing a particular mixing or blending procedure.
• the essentially anhydrous liquid polyfunctional organic detergent compositions of the present invention contain as essential ingredients, in the ranges of proportions set forth hereafter, (1) ethanolamine (i.e., monoethanolamine, diethanolamine and triethanolamine or mixtures of two or more thereof) salts of alkyl benzene sulfonic acids or alkyl toluene sulfonic acids, particularly the diethanolamine or triethanolamine salts of said sulfonic acids (2) certain ethanolamides or isopropanolamides, and (3) certain water-soluble nonionic organic detergents which are normally liquid or, in other words, liquid at usual room temperatures.
• ethanolamine i.e., monoethanolamine, diethanolamine and triethanolamine or mixtures of two or more thereof
• alkyl benzene sulfonic acids or alkyl toluene sulfonic acids particularly the diethanolamine or triethanolamine salts of said sulfonic acids
• certain ethanolamides or isopropanolamides
• alkyl benzene sulfonic acids and the alkyl toluene sulfonic acids which are utilized in the form of their ethanolamine salts as stated above, are those in which the alkyl radical, which may be linear or branched chain, contains predominately from 8 to 16 carbon atoms and, better still, from 11 to 15 carbon atoms.
• the alkyl radical which may be linear or branched chain, contains predominately from 8 to 16 carbon atoms and, better still, from 11 to 15 carbon atoms.
• dodecyl benzene sulfonic acid and tridecyl benzene sulfonic acid as well as mixtures thereof or mixtures in which one or the other or both predominate, in which the dodecyl and tridecyl radicals are essentially normal or straight chain.
• alkyl benzene or alkyl toluene sulfonic acids are well known in the art and are conventionally made by alkylating benzene or toluene with normal or straight chain chloroparaffins, polypropylenes, or olefins, although other sources of alkyl radicals can, of course, be utilized.
• the ethanolamine salts of the aforesaid sulfonic acids are formed and incorporated in the manner described below. It may be noted that it is important to the achievement of the results of the present invention, taken in conjunction with the other essential aspects of the invention, not only to utilize ethanolamine salts of the aforesaid sulfonic acids, because the alkali metal salts are not operative,
• the normally liquid water-soluble non-ionic surfactants which are utilized in the liquid detergent compositions of the present invention serve as primary surfactants as well as liquid carriers. They are, per se, well known and are exemplified mainly by ethylene oxide adducts or polyethenoxy ethers of (i) aliphatic monohydric alcohols, comprising straight chain and branched chain saturated and unsaturated alcohols containing at least 8 carbon atoms and generally up to 18 carbon atoms, particularly branched chain and fatty alcohols containing from 10 to 14 carbon atoms or (ii) alkyl phenols, particularly monoor di-alkyl phenols, in which the alkyl radicals contain a total of from 5 to 18 carbon atoms, especially mono-alkyl phenols in which the akyl radical contains from 8 to 12 carbon atoms.
• aliphatic monohydric alcohols comprising straight chain and branched chain saturated and unsaturated alcohols containing at least 8 carbon atoms and generally up
• the mol ratio of the ethylene oxide to the aforesaid alcohols or alkyl phenols in the adducts is variable within quite wide limits, generally being at least 4 to 20 or more mols of ethylene oxide to 1 mol of said alcohols or alkyl phenols, especialy 6 to mols of ethylene oxide to 1 of said alcohols or alkyl phenols.
• the especially desirable normally liquid non-ionic organic surfactants utilized will be the 6 to 10 mol ethylene oxide adducts of (i) straight chain or branched chain aliphatic monohydric alcohols or (ii) mono-alkyl phenols in which the alkyl radical contains from 8 to 12 carbon atoms.
• the ethanolamides and/or isopropanolamides which serve as viscosity builders and foam boosters in the liquid detergent compositions of the present invention, are the fatty acid monoethanolamides, diethanolamides and isopropanolamides in which the fatty acid acyl radical contains from 10 to 16 carbon atoms.
• Said amides should be either normally liquid or have melting points not higher than about 60 degrees C.
• the proportions of the ingredients, in terms of weight percent, comprising the liquid detergent compositions of the present invention are (A) from 30 to 90%, better still 45 to 75%, of the aforementioned ethanolamine salts of the alkyl benzeneor alkyl toluene-sulfonic acids, (B) from 5 to 35%, better still 15 to of the aforementioned non-ionic normally liquid, water-soluble surfacants, and (C) from 5 to better still 12 to 25 %,of the aforementioned fatty acid amides of monoethanolamine, diethanolamine or isopropanolamine.
• liquid detergent compositions made pursuant to the present invention wherein the aforesaid ethanolamine salts of the alkyl benzeneor alkyl toluene-sulfonic acid constitute from 52 to 64%, the aforesaid non-ionic surfactant constitutes from 22 to 30%, and the aforesaid fatty acid monoor diethanolamides or isopropanolamides constitute from 14 to 18% of the compositions.
• the polyfunctional essentially active stable liquid detergent compositions of the present invention it is particularly advantageous first to form a substantially homogeneous solution of the nonionic normally liquid water-soluble surfactant with an ethanolamine and then gradually add thereto, under conditions of agitation, the alkyl benzene sulfonic acid and/ or alkyl toluene sulfonic acid in an amount essentially to be neutralized by said ethanolamine thereby to form the ethanolamine salt of said sulfonic acid, the temperature of the mixture being controlled so as not to exceed about 100 C.
• non-ionic surfactant must comprise the vehicle in which in situ formation of the ethanolamine salt of the sulfonic acid is effected.
• stable compositions cannot be formed if the ethanolamine salt of the sulfonic acid is sought to be formed in situ in the ethanolamide and/or isopropanolamide per se.
• nonionic surfactant must be present during the in situ formation of the ethanolamine salt of the sulfonic acid.
• the polyfunctional essentially 100% active stable liquid detergent compositions of the present invention cannot be made by initially preparing an aqueous solution of the active ingredients and then evaporating off the water because, among other things, at a concentration of about 60% of the active ingredients, breakdown of the composition occurs and instability resu ts.
• Example 1 To 26 parts of the condensation product or adduct of 6 mols of ethylene oxide and 1 mol of a linear fatty alcohol having mainly 10 to 14 carbon atoms there was added 20 parts of diethanolamine. Then 40 parts of dodecyl benzene sulfonic acid (88% minimum activity) was slowly added, under conditions of agitation, the temperature of the reactants and the reaction mixture being maintained below 50 C. and, better still, between about 20 and 30 C. The forementioned amount of diethanolamine is the stoichiometric quantity required to neutralize the dodecyl benzene sulfonic acid. When the neutralization was complete, 14 parts of a superamide (made from 1 mol of coconut oil fatty acids and 1 mol of diethanolamine) was added, under conditions of agitation, until a clear, homogeneous liquid was obtained.
• a superamide made from 1 mol of coconut oil fatty acids and 1 mol of diethanolamine
• liquid detergent compositions The stability of said liquid detergent compositions was excellent, no separation of ingredients occurring after several months of aging at ambient temperatures and also at 0 C.
• the following table illustrates the slight degree of darkening of the final liquid detergent compositions as the temperature is increased. Readings were made on a Klett-Summerson Photoelectric Colorimeter. Readings were made immediately after neutralization and one hour after neutralization at the temperature indicated, to simulate conditions in the processing of large batches which would be difiicult to cool rapidly.
• Example 1(a) In sharp contrast to the results obtained in Example 1, when a detergent composition was sought to be made by simply mixing together 26 parts of the same 6-mo1 ethylene oxide adduct used in Example 1, 14 parts of the same superamide used in Example 1, and 60 parts of the sodium salt of dodecyl benzene sulfonic acid active, or in the form of an aqueous slurry as in the aforesaid Pat. No. 3,239,468), the resulting composition was unclear and unstable and quickly formed separate layers, including undissolved material.
• Example 1 (b) Again, when an essentially anhydrous detergent composition was sought to be made by simply admixing together 26 parts of the same 6-mol ethylene oxide adduct used in Example 1, 14 parts of the same superamide used in Example 1, and 60 parts of a preformed diethanolamine salt of dodecyl benzene sulfonic acid made by admixing 20 parts of diethanolamine with 40 parts of dodecyl benzene sulfonic acid (88% minimum activity), an extremely non-homogeneous, unclear composition resulted in which solids readily separated out.
• Example 1(c) A detergent composition was sought to be made y simply admixing together 30 parts of a IO-mol ethylene oxide adduct of nonylphenol, 50 parts of a coconut fatty acid-diethanolamine condensate (mol ratio of coconut fatty acidszdiethanolamine being 1:1), and 20 parts of the sodium salt of dodecyl benzene sulfonic acid (100% active or in the form of an aqueous slurry as in the aforesaid Pat. No. 3,239,468).
• the resulting composition was unclear and unstable, readily separating out into layers.
• Example 1(d) A detergent composition was sought to be made by simply admixing together 30 parts of a 10-mol ethylene oxide adduct of nonylphenol, 50 parts of a coconut fatty acid-diethanolamine condensate (mol ratio of coconut fatty acids:diethanolamine being 1:1), and 20 parts of a preformed diethanolamine salt of dodecyl benzene sulfonic acid.
• the resulting composition was extremely nonhomogeneous and unclear from which solids readily separated out. (Note the observations made in Example 1(b) regarding the matter of seeking to prepare the preformed diethanolamine salt of dodecyl benzene sulfonic acid.)
• Examples 1(c) and 1(d) are illustrative of compositions falling within the ranges of proportions of the stated ingredients disclosed in the aforesaid Pat. No. 3,239,468 sought to be made simply by mixing together said ingredients. These examples, as well as Examples 1(a) and 1(b), show that our polyfunctional essentially 100% active stable liquid detergent compositions are not obtainable by following the procedures described in said Examples 1(a), 1(b), 1(c) and 1(d).
• Example 2 Parts Diethanolamine 20 Linear dodecyl benzene sulfonic acid (88% active) 40 6-mol ethylene oxide adduct of C C fatty alcohols 18 Coconut oil fatty acid diethanolamide (1:1 mol ratio) 22
• Example 3 Parts Triethanolamine 25 Linear dodecyl benzene sulfonic acid (88% active) 35 9-mol ethylene oxide adduct of octyl phenol 22 Why acid diethanolamide (1:1 mol ratio) 18
• Example 4 Diethanolamine 14 Alkyl benzene sulfonic acid (98% active-branched chain alkyl radical containing predominately 11 carbon atoms) 41 6-mol ethylene oxide adduct of IZ-carbon atom secondary alcohol 30
• liquid detergent compositions of the present invention are 100% active essentially 100% active.
• some water may enter into the final liquid detergent compositions by reason of its presence in small proportions in one or more of the ingredients utilized in the preparation of said compositions.
• the method of preparation and the selection of ingredients should so be controlled that the water content of the final liquid detergent compositions does not exceed 2% of the total weight of said liquid detergent compositions.
• said compositions may contain up to 2% water.
• liquid detergent compositions of the present invention in addition to exhibiting excellent cleaning power for many commercial and consumer requirements including hard surface cleaning, have the important advantages of providing essentially 100% organic surfactant activity with the accompanying economic advantages in shipping and storing, and outstanding stability over prolonged periods of time over a wide temperature range.
• Said liquid detergent compositions are readily pourable or pumpable, and they can be diluted with water to various commercially acceptable concentrations, forming aqueous solutions which are also stable over a wide temperature range and for extended periods of time.
• A An ethanolamine salt of a member selected from the group consisting of alkyl benzeneand alkyl toluene-sulfonic acids in which the alkyl radical contains from 8 to 18 carbon atoms
• B Non-ionic normally liquid, water soluble surfactant in the form of a member selected from the group consisting of (i) ethoxylated aliphatic monohydric alcohols containing from 8 to 18 carbon atoms and (ii) ethoxylated alkyl phenols in which the alkyl radicals are l to 2 in number and contain a total of from 5 to 18 carbon atoms, subject to the proviso that the number of rnols of ethylene oxide in said surfactant is in the range of about 4 to about 20 mols per mol of said alcohols or alkyl phenols, as the case may be
• C Fatty acid amides selected from the group consisting of monoethanolamide, diethanolamide and isopropanolamide in which
• A An ethanolamine salt of a member selected from the group consisting of alkyl benzeneand alkyl toluene-sulfonic acids in which the alkyl radical contains from 8 to 18 carbon atoms
• B Non-ionic normally liquid, water soluble surfactant in the form of a member selected from the group consisting of (i) ethoxylated aliphatic monohydric alcohols containing from '8 to 18 carbon atoms and (ii) ethoxylated alkyl phenols in which the alkyl radicals are 1 to 2 in number and contain a total of from 5 to 18 carbon atoms, subject to the proviso that the number of mols of ethylene oxide in said surfactant is in the range of about 4 to about 20 mols per mol of said alcohols or alkyl phenols, as the case may be
• C Fatty acid amides selected from the group consisting of monoethanolamide, diethanolamide and isopropanolamide in which the
• the (B) ingredient is a 6 to mol ethylene oxide adduct of a member selected from the group consisting of (i) a fatty alcohol containing from 10 to 14 carbon atoms and (ii) an alkyl phenol in which the number of alkyl radicals is from 1 to 2 and the total number of carbon atoms in said alkyl radicals is between 8 and 12, and wherein the alkyl radical of said sulfonic acid contains predominately from I 11 to carbon atoms.
• sulfonic acid is a member selected from the group consisting of dodecyland tridecyl-benzene sulfonic acid
• the (B) ingredient is a 6 to 10 mol ethylene oxide adduct of a member selected from the group consisting of (i) a C -C fatty alcohol and (ii) a C to C alkyl phenol.
• the (B) ingredient is a 6 to 10 mol ethylene oxide adduct of a member selected from the group consisting of (i) a fatty alcohol containing from 10 to 14 carbon atoms and (ii) an alkyl phenol in which the number of alkyl radicals is from 1 to 2 and the total number of carbon atoms in said alkyl radicals is between 8 and 12, and wherein the alkyl radical of said sulfonic acid contains predominately from 11 to 15 carbon atoms.

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

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• 1966
  • 1966-11-28 DE DE1966W0042870 patent/DE1543970B2/de active Granted
  • 1966-11-28 GB GB53071/66A patent/GB1114359A/en not_active Expired
  • 1966-11-28 FR FR85225A patent/FR1501661A/fr not_active Expired
• 1970
  • 1970-11-19 US US00091153A patent/US3709838A/en not_active Expired - Lifetime
• 1972
  • 1972-11-29 US US00310293A patent/US3856711A/en not_active Expired - Lifetime
• 1973
  • 1973-07-31 CA CA177,699A patent/CA983806A/en not_active Expired
  • 1973-09-20 BE BE135837A patent/BE805077Q/xx not_active IP Right Cessation
  • 1973-11-06 DE DE2355402A patent/DE2355402C3/de not_active Expired
  • 1973-11-06 GB GB5150473A patent/GB1455283A/en not_active Expired
  • 1973-11-19 BE BE137925A patent/BE807519A/xx not_active IP Right Cessation
  • 1973-11-22 FR FR7341629A patent/FR2207980B2/fr not_active Expired

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