US3812044A - Detergent composition containing a polyfunctionally-substituted aromatic acid sequestering agent - Google Patents

Detergent composition containing a polyfunctionally-substituted aromatic acid sequestering agent Download PDF

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US3812044A
US3812044A US00102159A US10215970A US3812044A US 3812044 A US3812044 A US 3812044A US 00102159 A US00102159 A US 00102159A US 10215970 A US10215970 A US 10215970A US 3812044 A US3812044 A US 3812044A
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sodium
carbon atoms
acid
alkyl
water
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D Connor
H Krummel
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Procter and Gamble Co
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Procter and Gamble Co
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Priority to CA130,827A priority patent/CA947611A/en
Priority to BE777333A priority patent/BE777333A/xx
Priority to FR7146787A priority patent/FR2120915A5/fr
Priority to IT32984/71A priority patent/IT944403B/it
Priority to DE19712164872 priority patent/DE2164872A1/de
Priority to NL7117993A priority patent/NL7117993A/xx
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C07C309/58—Carboxylic acid groups or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/41—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
    • C07C309/42—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
    • C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof

Definitions

  • a detergent composition comprising a water-soluble organic synthetic detergent, and as a detergency aid, a sequestering agent which is a water-soluble salt of a polyfunctionally-substituted aromatic acid compound having the formula wherein at least two Rs are different functional groups of the type described.
  • Metal sequestering agents are frequently used as additives in detergent compositions of all types including household detergent compositions, e.g., laundry detergents and industrial compositions, e.g., hard-surface cleaning products. It is known, for instance, that when soaps are used in hard water, insoluble calcium and magnesium soaps are formed which detract considerably from the detergency objectives.
  • non-soap synthetic detergents are also adversely effected by the presence of hardness minerals, such as alkaline earth metals.
  • Condensed polyphosphates such as sodium tripolyphosphate and sodium pyrophosphate and nitrogen-containing compounds'such as sodium nitrilotriacetate are common examples of known sequestering agents useful as ingredients in detergent compositions.
  • sequestering agents such as sodium tripolyphosphate and sodium pyrophosphate and nitrogen-containing compounds'such as sodium nitrilotriacetate are common examples of known sequestering agents useful as ingredients in detergent compositions.
  • such additives are referred to as builders.
  • the enhanced cleaning is due to decreased adsorption of detergents and allied materials on the fabrics being washed or treated.
  • the phosphorus-content and nitrogen-content of such compositions may have adverse environmental effects, such as accelerated eutrophication of lakes and streams.
  • Eutrophication is a natural process which is vital to sustaining the life of any body of water by enabling plant organisms to grow in the water and thus provide food for fish.
  • a primary object of the present invention is to pro vide phosphateand nitrate-free detergent compositions which are effective in water solutions over a wide range of concentrations and pHs inasmuch as the conditions under which laundry is done vary widely with the individual and the locality. Another object is to provide improved heavy-duty laundry detergent compositions containing, as builders, sequestering agents selected from the novel classes of compounds described herein.
  • An improved detergent composition comprises a water-soluble organic synthetic detergent and, as a detergency aid, a sequestering agent which is a water-soluble salt of a polyfunctionally-substituted aromatic acid compound having the formula wherein each R represents --CH CH wherein X represents halogen;
  • R represents SO H
  • hydrogen, the lower alkyl groups such as methyl, ethyl, propyl, butyl, isobutyl, and the halogens and halogenated-alkyl groups are non-functional substituents.
  • the amount of sequestering agent required to aid in the detergency varies widely depending on many circum stances including the specific sequesterants properties, the detergent employed, the hardness content of the Water, the oil load and the nature of the substrate being washed or treated, and the like.
  • an effective or sufiicient amount is used, and this implies that a sulficient amount of sequesterant is used to render the water suitable for its intended purpose. This may be judged by various means, such as soap titration, observation of the clarity of the solution, or by a practical trial of the softened water for its intended purpose. A complete softening, although sometimes desirable, is in many cases not necessary.
  • the proportion by weight of the detergent to the sequestering agent is in the range of 20:1 to 1:20 and preferably :1 to 1:10. Within these ranges, compositions are represented which are lightly built or heavily built depending on the amount of sequestrant builder used.
  • compositions of this invention are effective over the broad pH range of about 6 to 12, but optimum cleaning results are achieved with ordinary alkaline detergents in the range of 8 to 12 and preferably 9 to 11.
  • the compositions can be formulated to provide a desired pH in the ranges by proper selection of appropriates salts.
  • preferred water-soluble salts for both the detergent and sequestering agent are alkali metal salts such as sodium, potassium, lithium and ammonium or alkylsubstituted ammonium, e.g. triethanol ammonium.
  • Sodium and potassium are preferred water-soluble cations.
  • the salts are partially or fully neutralized.
  • the detergent compositions can be prepared as solid (granular, tablet, powder) or liquid (aqueous or nonaqueous-based) physical forms.
  • Any water-soluble organic synthetic detergent can be used in conjunction with the novel class of sequestering builder agents of this invention and have its detergency properties improved.
  • the detergents include anionic, nonionic, ampholytic, and zwitterionic surface-active agents, or mixtures of such materials. Each of these classes of detergents is illustrated by the following listed compounds:
  • Anionic soap and non-soap synthetic detergents includes ordinary alkali metal soaps such as the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids containing from about 8 to about 24 carbon atoms and preferably from about 10 to about 20 carbon atoms.
  • Suitable fatty acids can be obtained from natural sources such as, for instance, from plant or animal esters (e.g., palm oil, coconut oil, babassu oil, soybean oil, castor oil, tallow, whale and fish oils, grease, lard, and mixtures thereof).
  • the fatty acids also can be synthetically prepared (e.g., by the oxidation of petroleum, or by hydrogenation of carbon monoxide by the Fischer-Tropsch process).
  • Resin acids are suitable such as resin and those resin acids in tall oil. Naphthenic acids are also suitable.
  • Sodium and potassium soaps can be made by direct saponification of the fats and oils or by the neutralization of the free fatty acids which are prepared in a separate manufacturing process. Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.
  • This class of detergents also includes water-soluble salts, particularly the alkali metal salts of organic sulfuric reaction products having in their molecular structure an alkyl radical containing from about 8 to about 22 carbon atoms and a sulfonic acid or sulfuric acid ester radical.
  • alkyl is the alkyl portion of higher acyl radicals.
  • this group of synthetic detergents which form a part of the preferred built detergent compositions of the present invention are the sodium or potassium alkyl sulfates, especially those obtained by sulfating the higher alcohols (C -C carbon atoms) produced by reducing the glycerides of tallow or coconut oil; sodium or potassium alkyl benzene sulfonates, in which the alkyl group contains from about 9 to about 15 carbon atoms, in straight chain or branched chain configuration, e.g., those of the type described in United States Letters Patents Numbers 2,220,099 and 2,477,383
  • C LAS linear straight chain alkyl benzene sulfonates in which the average of the alkyl groups is about 13 carbon atoms abbreviated hereinafter as C LAS
  • sodium alkyl glyceryl ether sulfonates especially those ethers of higher alcohols derived from tallow and coconut oil
  • anionic non-soap synthetic detergents which come within the terms of the present invention are the reaction product of fatty acids esterified with isethionic acid and neutralized with sodium hydroxide where, for example, the fatty acids are derived from coconut oil; sodium or potassium salts of fatty acid amide of methyl tauride in which the fatty acids, for example, are derived from coconut oil.
  • Other anionic synthetic detergents of this variety are set forth in United States Letters Patents 2,486,921; 2,486,922; and 2,396,278.
  • succinamates include the class designated as succinamates.
  • This class includes such surface active agents as disodium N-octadecylsulfo succinamate; tetrasodium N-(1,2-dicarboxyethyl)-N-octadecylsulfo-succinamate; diamyl ester of sodium sulfosuccinic acid; dihexyl ester of sodium sulfosuccinic acid; dioctyl ester of sodium sulfosuccinic acid.
  • Anionic phosphate surfactants are also useful in the present invention. These are surface active materials having substantial detergent capability in which the anionic solubilizing group connecting hydrophobic moieties is an oxy acid of phosphorus.
  • the more common solubilizing groups are --SO H, SO H, and CO H.
  • Alkyl phosphate esters such as (R-O) PO H and ROPO H in which R represents an alkyl chain containing from about 8 to about 20 carbon atoms are useful.
  • esters can be modified by including in the molecule from one to about 40 alkylene oxide units, e.g., ethylene oxide units.
  • Formulae for these modified phosphate anionic detergents are o ta-oonzornomi -o-u in which R represents an alkyl group containing from about 8 to 20 carbon atoms, or an alkylphenyl group in which the alkyl group contains from about 8 to 20 carbon atoms, and M represents a soluble cation such as hydrogen, sodium, potassium, ammonium or substituted ammonium; and in which n is an integer from 1 to about 40.
  • Said Component A is a mixture of double-bond positional isomers of water soluble salts of alkene-l sulfonic acids containing from about 10 to about 24 carbon atoms, said mixture of positional isomers including about 10% to about 25% of an alpha-beta unsaturated isomer, about 30% to about 70% of a beta-gamma unsaturated isomer, about 5% to about 25% of a gamma-delta unsaturated isomer, and about 5% to about 10% of a deltaepsilon unsaturated isomer;
  • Said Component B is a mixture of water soluble salts of bifunctionally-substituted sulfur-containing saturated aliphatic compounds containing from about 10 to about 24 carbon atoms, the functional units being hydroxy and sulfonate radicals with the sulfonate radical always being on the terminal carbon and the hydroxyl radical being attached to a carbon atom at least two carbon atoms removed from the terminal carbon atom, at least 90% of the hydroxy radical substitutions being in the 3, 4, and positions; and
  • Said Component C is a mixture comprising from about 30-95% water soluble salts of alkene disulfonates containing from about to about 24 carbon atoms, and from about 5% to about 70% water soluble salts of hydroxy disulfonates containing from about 10 to about 24 carbon atoms, said alkene disulfonates containing a sulfonate group attached to a terminal carbon atom and a second sulfonate group attached to an internal carbon atom not more than about six carbon atoms removed from said terminal carbon atom, the alkene double bond being distributed between the terminal carbon atom and about the seventh carbon atom, said hydroxy disulfonates being saturated aliphatic compounds having a sulfonate radical attached to a terminal carbon, a second sulfonate group attached to an internal carbon atom not more than about six carbon atoms removed from said terminal carbon atom, and a hydroxy group attached to a carbon atom which is not more than about four carbon atoms removed
  • Nonionic synthetic detergents may be broadly defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature.
  • the length of the hydrophilic or polyoxyalkylene radical which is condensed with any partic'ular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
  • Pluronic a well known class of nonionic synthetic detergents is made available on the market under the trade name of Pluronic. These compounds are formed by condensing ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol.
  • the hydrophobic portion of the molecule which, of course, exhibits water insolubility, has a molecular weight of from about 1500 to 1800'.
  • the addition of polyoxyethylene radicals to this hydrophobic portion tends to increase the water solubility of the molecule as a whole and the liquid character of the product is retained up to the point where polyoxyethylene content is about 50% of the total weight of the condensation product.
  • nonionic synthetic detergents include:
  • the polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration, with ethylene oxide, the said ethylene oxide being present in amounts equal to S to 25 moles of ethylene oxide per mole of alkyl phenol.
  • the alkyl substituent in such compounds may be derived from polymerized propylene, diisobutylene, octene, or nonene, for example.
  • Nonionic detergents include nonyl phenol condensed with either about 10 or about 30 moles of ethylene oxide per mole of phenol and the condensation products of coconut alcohol with an average of either about 5.5 or about 15 moles of ethylene oxide per mole of alcohol and the condensation product of about 15 moles of ethylene oxide with one mole of tridecanol.
  • a detergent having the formula -R R R N 0 (amine oxide detergent) wherein R is an alkyl group containing from about 10 to about 28 carbon atoms, from 0 to about 2 hydroxy groups and from 0 to about 5 other linkages, there being at least one moiety of R which is an alkyl group containing from about 10 to about 18 carbon atoms and '0 ether linkages, and each R and R are selected from the group consisting of alkyl radicals and hydroxalkyl radicals containing from 1 to about 3 carbon atoms;
  • amine oxide detergents include:
  • dimethyltetradecylamine oxide dimethyltetradecylamine oxide, ethylmethyltetradecylamine oxide, cetyldimethylamine oxide, dimethylstearylamine oxide, cetylethylpropylamine oxide, diethyldodecylamine oxide, diethyltetradecylamine oxide, dipropyldodecylamine oxide, bis-(Z-hydroxyethyl)dodecylamine oxide, bis-(2-hydroxyethyl)-3-dodecoxyl-hydroxypropylamine oxide, (2-hydroxypropyl) methyltetradecylamine oxide, dimethyloleylamine oxide, dimethyl- (2-hydroxydodecyl)amine oxide,
  • a detergent having the formula R R R P O phosphine oxide detergent
  • R is an alkyl group containing from about 10 to about 28 carbon atoms, from 0 to about 2 hydroxy groups and from 0 to about 5 ether linkages, there being at least one moiety of R' which is an alkyl group containing from about 10 to about 18 carbon atoms and 0 ether linkages, and each of R and R are selected from the group consisting of alkyl radicals and hydroxyalkyl radicals containing from 1 to about 3 carbon atoms.
  • phosphine oxide detergents include:
  • dimethyldodecylphosphine oxide dimethyltetradecylphosphine oxide, ethylmethyltetradecylphosphine oxide, cetyldimethylphosphine oxide, dimethylstearylphosphine oxide, cetylethylpropylphosphine oxide,
  • diethyldodecylphosphine oxide diethyltetradecylphosphine oxide, dipropyldodecylphosphine oxide,
  • Ampholytic synthetic detergents can be broadly described as derivatives of aliphatic or aliphatic derivatives of heterocyclic secondary and tertiary amines, in which the aliphatic radical may be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and at least one contains an anionic water-solubilizing group, e.g., carboxyl, sulfo, sulfato, phosphate, or phosphono. Examples of compounds falling within this definition are sodium 3-(dodecylamino)-propionate,
  • Zwitterionic synthetic detergents can be broadly described as derivatives of aliphatic quaternary ammonium and phosphonium or tertiary sulfonium compounds, in which the cationic atom may be part of a heterocyclic ring, and in which the aliphatic radical may be straight chain or branched, and wherein one of the aliphatic substituents contains from about 3 to 18 carbon atoms, and at least one aliphatic substituent contains an anionic watersolubilizing group, e.g., carboxy, sulfo, sulfato, phosphato, or phosphono. Examples of compounds falling within this definition are 3 (N,N-dimethyl-N-hexadecyl-ammonio) -2-hydroxypropane-l-sulfonate,
  • calcium insensitive detergents which represent a preferred embodiment of the present invention when and in conjunction with the sequestering agents described above are those identified herein as calcium insensitive detergents.
  • the term calcium insensitive is a functional descriptive term used to designate a class of detergents whose detergency performance properties are not as adversely effected by water hardness minerals as, for instance, soap.
  • these detergents are efiicient in soil-removal and soil-dispersal in concentration of about 0.05% in water and, in addition, are soluble in water to at least a concentration of 0.05% at a temperature of about F. to about F.
  • Such materials include water-soluble (sodium or potassium) salts of sulfonated fatty acid esters of fl-acyloxyalkane-l-sulfonic acids; p-alkyloxyalkane sulfonates; alkyl polyethylene sulfates or olefin sulfonates.
  • Anionic organic detergents which are calcium insensitive in the terms described above include alkali metal, ammonium and substituted-ammonium salts of esters of an a-sulfonated fatty acid in which the esters contain about 15 to about 25 carbon atoms. These detergent compounds have the following structure:
  • R is alkyl or alkenyl of about 10 to about 20 carbon atoms (forming with the two carbon atoms a fatty acid group); R is alkyl of 1 to about 10 carbon atoms; and M is a salt-forming radical.
  • the salt-forming radical M in the hereinbefore described structural formula is a water-solubilizing cation and can be, for example, an alkali metal cation (e.g., sodium, potassium, lithium), ammonium or substitutedammonium cation.
  • alkali metal cation e.g., sodium, potassium, lithium
  • substituted ammonium cations include methyl-, dimethyl-, and trimethyl-ammonium cations and quaternary ammonium cations such as tetramethyl-ammonium and dimethyl piperidinium cations and those derived from alkylamines such as ethylamine, diethylamine, triethylamine, mixtures thereof, and the like.
  • this class of compounds include the sodium and potassium salts of esters where R; is selected from methyl, ethyl, propyl, butyl, hexyl and octyl groups and the fatty acid group (R plus the two carbon atoms in the structure above) is selected from lauric, myristic, palmitic, stearic, palmitoleic, oleic, linoleic acids and mixtures thereof.
  • a preferred ester material herein is the sodium salt of the methyl ester of u-sulfonated tallow fatty acid, the term tallow indicating a carbon chain distribution approximately as follows: C -2.5%, C 28%, O -23%, palmitoleic-2%, oleic41.5%,
  • Suitable salts of a-sulfonated fatty esters include the ammonium and tetramethylammonium salts of the hexyl, octyl, ethyl, and butyl esters of u-sulfonated tridecanoic acid; the potassium and sodium salts of the ethyl, butyl, hexyl, octyl, and decyl esters of a-sulfonated pentadecanoic acid; and the sodium and potassium salts of butyl, hexyl, octyl, and decyl esters of a-sulfonated heptadecanoic acid; and the lithium and ammonium salts of butyl, hexyl, octyl, and decyl esters of u-sulfonated nonadecanoic acid.
  • Suitable calcium insensitive anionic organic detergents includes salts of 2-acyloxy-alkane-l-sulfonic acids. These salts have the formula where R is alkyl of about 9 to about 23 carbon atoms (forming with the two carbon atoms an alkaline group); R is alkyl of 1 to about 8 carbon atoms; and M is a saltforming radical hereinbefore described.
  • Preferred fl-acyloxy-alkane-l-sulfonate salts herein are the alkali metal salts of B-acetoxy-alkane-l-sulfonic acids corresponding to the above formula wherein R is an alkyl of about 14 to about 18 carbon atoms, these salts being preferred from the standpoints of the excellent cleaning properties and ready availability.
  • alkyl ether sulfates are alkyl ether sulfates. These materials have the formula RO(C H O),,SO M wherein R is alkyl or alkenyl of about 10 to about 20 carbon atoms, x is 1 to 30, and M is a salt-forming cation defined hereinbefore.
  • the alkyl ether sulfates calcium insensitive detergents of the present invention are condensation products of ethylene oxide and monohydride alcohols having about 10 to about 20 carbon atoms.
  • R has 14 to 18 carbon atoms.
  • the alcohols can be derived from fats, e.g., coconut oil or tallow, or can be synthetic. Lauryl alcohol and straight chain alcohols derived from tallow are preferred herein. Such alcohols are reacted with 1 to 30, and especially 3 to 6, molar proportions of ethylene oxide and the resulting mixture of molecular species, having, for example,.an average of 3 to 6 moles of ethylene oxide per mole of alcohol, is sulfated and neutralized.
  • alkyl ether sulfates of the present invention are sodium coconut alkyl ethylene glycol ether sulfate; lithium tallow alkyl triethylene glycol ether sulfate; sodium tallow alkyl hexaoxyethylene sulfate; and ammonium tetradecyl octaoxyethylene sulfate.
  • alkali metal coconutand tallow-alkyl oxyethylene ether sulfates having an average of about 1 to about 10 oxyethylene moieties.
  • the alkyl ether sulfates of the present invention are known compounds and are described in U.S. Pat. 3,332,876 to Walker (July 25, 1967) incorporated herein by reference.
  • a preferred class of calcium insensitive anionic organic detergents are the fl-alkyloxy alkane sulfonates. These compounds have the following formula:
  • R is a straight chain alkyl group having from 10 to 20 carbon atoms
  • R is a lower alkyl group having from 1 to 3 carbon atoms
  • M is a salt-forming radical hereinbefore described.
  • ,EZ-alkoxy alkane sulfonates or alternatively 2 alkoxy-alkane 1 sulfones utilizable herein to provide superior cleaning and whitening levels under household washing conditions
  • olefin sulfonates having about 12 to about 24 carbon atoms.
  • olefin sulfonates is used herein to mean compounds which are produced by the sulfonation of u-olefin by means of uncomplexed sulfur trioxide, followed by neutralization of the acid reaction mixture in conditions such that any sultones which have been formed in the reaction are hydrolyzed to give the corresponding hydroxy-alkanesulfonates.
  • the sulfur trioxide may be liquid or gaseous, and is usually, but not necessarily, diluted by inert diluents, for example by liquid S0 chlorinated hydrocarbon, etc., when used in the liquid form, or by air, nitrogen, gaseous 50;, etc., when used in the gaseous form.
  • inert diluents for example by liquid S0 chlorinated hydrocarbon, etc., when used in the liquid form, or by air, nitrogen, gaseous 50;, etc., when used in the gaseous form.
  • the m-olefins from which the olefin sulfonates are derived are mono-olefins having 12 to 24 carbon atoms, preferably 14 to 16 carbon atoms. Preferably, they are straight chain olefins.
  • suitable l-olefins include l-dodecene; l-tetradecene; l-hexadecene; l-octadecene; l-eicosene and l-tetracosene.
  • the olefin sulfonates can contain minor amounts of other materials, such as alkene disulfonates depending upon the reaction conditions, proportions of reactants, the nature of the starting olefins and impurities in the olefin stock and side reactions during the sulfonation.
  • Calcium insensitive ampholytic synthetic detergents utilizable herein have the formula wherein R is alkyl of about 8 to about 18 carbon atoms, R is alkyl of 1 to about 3 carbon atoms or is hydrogen, R is alkylene of 1 to about 4 carbon atoms, Z is carboxy,
  • M is a salt-forming cation.
  • compounds falling within this'definition are sodium 3-dodecylaminopropionate; sodium 3-dodecylaminopropane sulfonate; N-alkyltaurines such as the ones prepared by reacting dodecylamine with sodium isethionate according to the teaching of U.S. Pat. 3,658,072; sodium salts of N-higher alkyl aspartic acids such as those produced according to the teaching of U.S. Pat. 2,438,- 091; and the products sold under the trade name Miranol and described in U.S. Pat. 2,528,378.
  • Calcium insensitive zwitterionic synthetic detergents in which the aliphatic radicals can be straight chain or branched, and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate or sulfate.
  • a general formula for these compounds is:
  • R contains an alkyl, alkenyl, or hydroxyalkyl radical of from about 8 to about 18 carbon atoms having from to about 10 ethylene oxide moieties and from 0 to 1 glyceryl moiety;
  • Y is selected from the group consisting of nitrogen and sulfur atoms;
  • R is an alkyl or monohydroxy alkyl group containing 1 to about 3 carbon atoms;
  • x is 1 when Y is a sulfur atom and 2 when Y is a nitrogen atom, R is an alkylene or hydroxy alkylene of from 1 to about 4 carbon atoms and
  • Z is a radical selected from the group consisting of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.
  • Examples include:
  • Examples of compounds falling within this definition are 3 (-N,N-dimethyl-N-hexadecylammonio)propane-1- sulfonate and 3 (N,N-dirnethyl-N-tridecylammonio)-2- hydroxypropane-l-sulfonate which are especially preferred for their excellent cool water detergency characteristics.
  • the alkyl groups contained in said detergent surfactants can be straight or branched, preferably straight, and saturated or unsaturated as desired.
  • a water-soluble sodium carboxymethyl cellulose can be added in minor amounts to inhibit soil redeposition or for other reasons.
  • Tarnish inhibitors such as benzotriazole or ethylenethiourea can also be added in amounts up to about 3%.
  • Fluorescers, enzymes, and brighteners, perfumes, coloring agents, while not per se essential in the compositions of this invention, can be added in minor amounts.
  • an alkaline material or alkali such as sodium or potassium hydroxide can be added as supplementary pH adjusters.
  • Other usual additives include sodium sulfate, sodium carbonate, water and the like.
  • Corrosion inhibitors are also frequently used.
  • Water-soluble silicates are highly effective corrosion inhibitors and can be added if desired'at levels of from about 3% to about 8% by weight of the total composition.
  • Alkali metal, preferably potassium and sodium silicates are preferred having a weight ratio of SiO :M O of from about 1.0:1 to 2.8:1 (M refers to sodium or potassium.)
  • Sodium silicate having a ratio of SiO :Na O of from about 1.621 to 2.45:1 is especially preferred.
  • a hydrotropic agent may be found desirable.
  • Suitable hydrotropes are water-soluble alkali metal salts of toluenesulfonate, benzenesulfonate, and xylene sulfonate.
  • Preferred hydrotropes are potassium or sodium toluenesulfonates.
  • the hydrotrope may be added, if desired, at levels of from 0% up to about 12%. While a hydrotrope will not ordinarily be found necessary, it can be added, if so desired, for any reason such as to function as a solubilizing agent and to produce a product which retains its homogeneity at a low temperature.
  • An effective granular laundry detergent composition according to this invention has the following formulation.
  • the sequestering agent in the preceding example can be replaced with an equal weight proportion of sodium- 1,3,5-trihydroxy-2,4,6-benzene tricarboxylate, or sodium- 1,3,5-trihydroxy-2,4,6-benzene triacetate and an effective composition is obtained.
  • the evaluations are run in 200 ml. beakers at 23 i3 C. with a magnetic stirrer. 50 ml. 14 gram/ gal. (calculated as Caflo CaCl solution is poured into the breaker. The requisite amount of sequestering agent (builder) sample to give a final solution concentration of 0.06%, 0.03%, or 0.02%, is weighed or pipetted into the beaker. The sample is brought to pH 7 with KOH or HCl as needed. Distilled water is added to give a total volume of :3 ml. Fine adjustment is made to pH 7.00:0.05 with a Corning Model 12 meter and Corning Model 476022 glass electrode.
  • the synthesis methods for preparing the sequestering agents represent no part of this invention. While any known reactions can be used, the following examples are given to illustrate successful preparative methods. The sequestration values are given with several of the following examples.
  • another embodiment of the present invention is to provide a process for treating aqueous solutions containing polyvalent metal ions by adding to the solution an efiective amount of at least one of the novel class of sequestering agents described and illustrated above. Ordinarily, this amount ranges from .25 p.-p.m. to 10,000 p.p.m of the aqueous solution.
  • This embodiment of the present invention is based on the discovery of the sequestering properties of the sequestering agents described herein.
  • the manner of synthesizing the sequestering agents of this invention form no part of this invention.
  • Any suitable reaction can be used.
  • sulfonations are effected by reaction of the arcmatic-based material with in such solvents as HCl, H 80 $0 or H O.
  • Carboxy groups are formed by adding previously carboxylated materials to aromatics by oxidation of methyls or chloromethyls with H 0 potassium dichromate, potassium permanganate, or nitric acid.
  • Phenolic OH groups are added by means of alkali fusion of aromatics or by means of acidification of hydroperoxides of isopropyl aromatics
  • Alcoholic OH groups are added by reacting chloromethyl aromatics with aqueous NaOH or KOH. These procedures and the others used are adapted as needed so as to obtain the desired end product. The aforementioned processes are more fully described in Organic Chemistry by R. T. Morrison and R. N. Boyd, published by Allyn and Bacon, Inc. in 1962.
  • 3,6-dihydroxybenzene-l,2,4,5-tetracarboxylic acid and related compounds can be prepared by the procedure described in detail in J. U. Nef Annalen der Chemie 237, l-35 (1887).
  • sequestering agents which come within the novel class of the sequestering agents of this invention such as phenol-2,4,6-trisulfonic acid can be prepared according to the procedure described in Senhofer, Ann 170, 110.
  • a detergent composition consisting essentially of a water-soluble organic synthetic detergent selected from the group consisting of anionic, nonionic, ampholytic and zwitterionic surface active agents and mixtures thereof, and as a detergency aid a sequestering agent which is a water-soluble salt selected from the group consisting 22 of alkali metal salts and ammonium salts of a polyfunctionally-substituted aromatic compound having the formula HO OH OOH and wherein the proportion by weight of the organic synthetic detergent to the sequestering agent is in the range of 20:1 to 1:20.
  • a detergent composition of claim 1 wherein the sequestering agent is the trisodium salt of 1,3,5-trihydroxy-2,4,6-benzene tricarboxylic acid.

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US00102159A 1970-12-28 1970-12-28 Detergent composition containing a polyfunctionally-substituted aromatic acid sequestering agent Expired - Lifetime US3812044A (en)

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US00102159A US3812044A (en) 1970-12-28 1970-12-28 Detergent composition containing a polyfunctionally-substituted aromatic acid sequestering agent
CA130,827A CA947611A (en) 1970-12-28 1971-12-22 Detergent composition containing a polyfunctionally-substituted aromatic acid sequestering agent
BE777333A BE777333A (fr) 1970-12-28 1971-12-27 Composition detergente contenant un agent
FR7146787A FR2120915A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1970-12-28 1971-12-27
IT32984/71A IT944403B (it) 1970-12-28 1971-12-27 Composizione detergente che contie ne un agente sequestrante a base di un acido aromatico polifunzio nalmente sostituito
DE19712164872 DE2164872A1 (de) 1970-12-28 1971-12-27 Wasch- und Reinigungsmittelmischung
NL7117993A NL7117993A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1970-12-28 1971-12-28

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