US3308067A - Polyelectrolyte builders and detergent compositions - Google Patents

Polyelectrolyte builders and detergent compositions Download PDF

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US3308067A
US3308067A US269359A US26935963A US3308067A US 3308067 A US3308067 A US 3308067A US 269359 A US269359 A US 269359A US 26935963 A US26935963 A US 26935963A US 3308067 A US3308067 A US 3308067A
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builder
acid
sodium
compounds
detergent
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Francis Louvaine Diehl
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Procter and Gamble Co
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Procter and Gamble Co
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Priority to AU41946/64A priority patent/AU293474B2/en
Priority to FI0537/64A priority patent/FI42739B/fi
Priority to GB1285864A priority patent/GB1054755A/en
Priority to DE19641467656 priority patent/DE1467656B2/de
Priority to AT277164A priority patent/AT278215B/de
Priority to FR969267A priority patent/FR1476512A/fr
Priority to CH410964A priority patent/CH490491A/de
Priority to DK161064AA priority patent/DK119268B/da
Priority to SE04013/64A priority patent/SE328362B/xx
Priority to NL6501871A priority patent/NL132878C/nl
Priority to BE685413D priority patent/BE685413A/xx
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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/24—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms containing more than three carboxyl groups
    • 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
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof

Definitions

  • This invention relates to cleansing and laundering compositions, and more particularly, cleansing and laundering compositions containing polyelectrolyte builder mate rials that serve to enhance the cleaning capacity of detergent compounds.
  • builder materials are water-soluble inorganic alkaline builder salts which can be used alone or in combination, including alkali metal carbonates, borates, phosphates, polyphosphates, bicarbonates and silicates.
  • organic builder materials are alkali metal, ammonium or substituted ammonium aminopolycarboxylates, e.g., sodium and potassium ethylenediaminetetraacetate, sodium and potassium N(2-hydroxyethyl)- ethylenediaminetriacetate, sodium and potassium and triethanolammonium N (Z-hydroxyethyl)-nitrilodiacetate.
  • Alkali metal salts of phytic acid e.g., sodium phytate, are also suitable as organic builders.
  • a further object is to provide a new class of highly effective polyelectrolyte'builder compounds comprising Watersoluble salts of polymeric aliphatic polycarboxylic acids, as described hereinafter.
  • Another object is to provide built detergent compositions containing members of the newly discovered class of polyelectrolyte builder materials.
  • FIGURE'I is a graph showing cleaning grades obtained as a function of builder con centration of several representative polyelectrolyte builder compounds, as hereinafter more fully described.
  • the water-soluble salt can be alkali metal or ammonium or substituted ammonium salt.
  • the alkali metal can be sodium or potassium.
  • the salt can be used in a partially or fully neutralized form.
  • the essential structural features which are necessary in order for the water-soluble salts of polymeric aliphatic polycarboxylic acids to have builder properties are the following:
  • X, Y, and Z are each selected from the group consisting of hydrogen, methyl, carboxyl and canboxymethyl; at least one of X, Y, and Z being selected from the group consisting of carboxyl and carboxymethyl, provided that X and Y can be carboxymethyl only when Z is selected from carboxyl and carboxymethyl; wherein only one of X, Y and Z can he methyl, and wherein n is a whole integer having a value within a range, the lower limit of which is three and the upper limit of which is determined primarily by the solubility characteristics of the salts in an aqueous system.
  • Examples of these compounds are water-soluble salts of the following aliphatic polycarboxylic acids: Poly (maleic acid), poly (itaconic acid), poly(m-esaconic acid), poly(fumaric acid), poly(aconitic acid), poly(methylenemalonic acid), poly(citraconic acid), etc.
  • each R is selected from the group consisting of hydrogen, methyl, carboxyl, carboxymethyl and carboxyethyl; wherein only one R can be methyl; where m is at least 45 mole percent of the copolymer, wherein X, Y, Z are each selected from the group consisting of hydrogen, methyl, carboxyl and carboxymethyl, at least one of X, Y, and Z being selected from the group consisting of carboxyl and carboxymethyl, provided that X and Y can be carboxymethyl only when Z is selected from carboxyl and carboxymethyl; wherein only one of X, Y, and Z can be methyl; and wherein n is a whole integer within a range, the lower limit of Which is three and the upper limit of which is determined primarily by the solubility characteristics of the salts in an aqueous system.
  • the polymers described herein can be linear polymers or they may even be of a branched or cross-linked variety, provided that they are soluble to the extent described hereinafter as being necessary.
  • Examples of compounds which suitably can be copolymerized with the polycarboxylic acids mentioned in subparagraph (a) and which do not interfere with desirable solubility characteristics in aqueous systems are ethylene, propylene, acrylic acid, methacrylic acid, crotonic acid, 3-butenoic acid, 3-methyl-3-buytenoic acid.
  • copolymeric compounds wherein the ratios are mole ratios, are 1:1 copolymer of ethylene and itaconic acid with an equivalent weight of 79; a 1:1 copolymer of propylene and maleic acid with an equivalent weight of 79; a 1:3 copolymer of acrylic acid and itaconic acid with an equivalent Weight of 66; a 1:4 copolymer of 3-buten0ic acid and maleicacid with an equivalent weight of 61.1; a 1:9 copolymer of isocrotonic acid and citraconic acid with an equivalent weight of 66.2; a 1:1.9 copolymer of methacrylic acid and aconitic acid with an equivalent weight of 62.2; a 1.211 copolymer of a 4- pentenoic acid and itaconic acid, with an equivalent weight of 78.3.
  • equivalent weights are calculated as the acid form.
  • equivalent weight as used herein has the usual meaning ascribed to that term. It implies the equivalent of a substance in grams, which is calculated by dividing its formula weight by its valency. In the present case of the acids, the valency is the number of replaceable hydrogen atoms.
  • interfering radical substituents include methoxy, acetoxy, dimethyl, and phenyl as illustrated by the following monomers; vinyl methyl ether, vinyl acetate, isobutylene, acrylamide and styrene.
  • copolymers are outside the limits of suitable compositions according to this invention: 1:1 copolymer of vinyl methyl ether and maleic acid, 1:1 copolymer of vinyl acetate and itaconic acid, 1:1 copolymer of isobutylenc and maleic acid, 1:1 copolymer of acrylamide and aconitic acid, and 1:1 copolymer of styrene and maleic acid.
  • the monomeric species employed can in many cases, be such derivatives or precursors of the designated acids as the anhydrides, the full or partial esters of such acids, amides, nitriles, etc., or mixtures of same, which after polymerization can be converted to the carboxylate salts by appropriate chemical reactions.
  • maleic anhydride was polymerized using 5% benzoyl peroxide as initiator following the procedure described by Lang, Paveli-ch and Clarey in I. Polymer Sci., issue 162, p. S32 (1961) and subsequently converted to sodium polymaleate by treatment with aqueous sodium hydroxide, a highly preferred builder polymer was obtained.
  • Use of potassium hydroxide in place of sodium hydroxide also yields a highly preferred builder which is particularly desirable for use in liquid formulations because of its excellent solubility.
  • copolymers of ethylene and maleic anhydride, methyl acrylate and ethyl fumarate, ethyl aconitate and ethyl itaconate, acrylonitrile and butyl maleate, etc., and homopolymers of ethyl fumarate, itaconic anhydride, etc. will upon conversion to the carboxylate salts yield suitable builder materials provided that such materials are also within the limits defined hereinbefore and hereinafter.
  • the preferred builder compounds of this invention either have carboxyl groups attached to vicinal carbon atoms along the polymer chain such as in fumaric and maleic acids, or they have a carboxyl group and a carboxyl containing group attached geminally to a carbon atom of the polymer chain.
  • An example of this latter configuration is itaconic acid.
  • Aconitic acid as illustrated hereinafter, has a carboxymethyl radical and a carboxyl radical attached to the same carbon atom as well as vicinally located carboxyl groups.
  • two carboxyl groups can be geminally attached to a carbon along the polymer chain, for example, polytmethylenemalonic) acid.
  • Such polymeric compounds may tend to decarboxylate under certain conditions of use. For this reason, the fact that such compounds may, on occasion, involve special processing and formulating considerations, this type of geminally carboxylated builder is less preferred.
  • Aconitic acid, C H O also called 1,2,3-propenetricarboxylic acid is a tribasic acid obtained from Aconitum equisetum, Adones and Achellea species, or can be made from citric acid. It also occurs in beets and sugar cane and has the following structural formula:
  • the higher builder concentrations on the order of 50% by weight may be found necessary under certain washing conditions such as a water hardness of 21 grains equivalent CaCO per gallon or higher.
  • any of the polyelectrolyte builder compounds of this invention could be selected whose solubility characteristics would allow a builder concentration in an aqueous solution to the necessary amount.
  • builder concentrations of 03% to about .06% are found to be adequate.
  • the degree of polymerization of these compounds can vary within a very wide range.
  • the degree of polymerization, n can be within the range of 3 to about 5,000. This corresponds to a molecular weight range for the compounds of this invention from 350 to about 1,500,000.
  • a preferred range for the degree of polymerization, n is from about 4 to about 500. This represents a preferred molecular weight range for the polyelectrolyte builder compounds of this invention of about 500 to about 175,000.
  • the minimum molecular weight of 350 mentioned above was arrived at empirically and, to a great extent, is based on the knowledge and experience acquired from working with these polyelectrolytic polycarboxylic polymers.
  • Viscosity is a property more frequently used by polymer chemists as characterizing polymeric compounds than are molecular weights. This is no doubt due to the comparatively easier and less complicated methods for obtaining viscosity data. To make such data meaningful, it is necessary to also give the test conditions under which the measurements were run. Since there is a recognized correlation between the viscosity of polymeric compounds and their relative molecular weights and since such figures can be more meaningful and can frequently be more available than molecular weights, the polymeric builder compounds used in the examples of this invention are characterized in terms of specific viscosity. In all cases the viscosity characterization corresponds to a molecular weight substantially above 350.
  • the essential ingredients are (a) an organic water soluble detergent surface active material as defined and illustrated below and (b) a novel polyelectrolyte builder compound meeting the structural requirements specified and exemplified above.
  • the detergent'compositions of this invention therefore, contain the essential ingredients in a ratio of polyelectrolyte builder to detergent surfactant in the range of about 1:3 to about 10:1 by weight, with such compositions providing in aqueous solution a pH of about 9 to about 12.
  • the preferred ratio of polyelectrolyte builder to detergent surfactant is about 1:2 to about 5:1 and the optimum pH range is 9.5 to about 11.5.
  • the detergent surface active compounds which can be used within the compositions of this invention include anionic, nonionic, zwitterionic, ampholytic detergent compounds and mixtures thereof. These suitable substances are outlined at length below.
  • Anionic detergent compositions which can be used in the compositions of this invention include both soap and non-soap detergent compounds.
  • suitable soaps are the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids (C -C
  • Particularly useful are the sodium or potassium salts of the mixtures of fatty acids derived from coconut oil and tal low, i.e., sodium or potassium tallow and coconut soap.
  • anionic organic non-soap detergent compounds are the water soluble salts, 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 radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals.
  • alkyl is the alkyl portion of higher acyl radicals.
  • the synthetic detergents which form a part of the 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 coco-nut oil; sodium or potassium alkyl benzenesulfonates, such as are described in United States Letters Patents No. 2,220,009 and No.
  • alkyl group contains from about 9 to about carbon atoms
  • alkali metal alkylbenzene sulfonates are those in which the alkyl radical is a straight chain aliphatic radical containing from about 10 to about carbon atoms for instance, Z-phenyl-dodecanesulfcnate and 3-phenyl-dodcanesulfonate
  • sodium alkyl glyceryl ether sulfonates especially those ethers of the higher alcohols derived from tallo-w and coconut oil
  • Nonionic synthetic detergents may be broadly defined as compounds alphatic or aikylaromatic in nature which do not ionize in water solution.
  • 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 an 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 1,500 to 1,800.
  • 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 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 10 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.
  • R R R N+O Long chain tertiary amine oxides corresponding to the following general formula, R R R N+O, wherein R is an alkyl radical of from about 8 to 18 carbon atoms, and R and R are each methyl or ethyl radicals.
  • the arrow in the formula is a conventional representation of a semipolar bond.
  • amine oxides suitable for use in this invention include dimethyldo-decylamine oxide, dimethyloctylamine oxide, dimethyldecylamine oxide, dimethyltetradecylamine oxide, dimethylhexadecylamine oxide.
  • RRR"P O Long chain tertiary phosphine oxides corresponding to the following formula RRR"P O, wherein R is an alkyl, alkenyl or monohydroxyalkyl radical ranging from 10 to 18 carbon atoms in chain length and R and R" are each alkyl or monohydroxyalkyl groups containing from 1 to 3 carbon atoms.
  • R and R" are each alkyl or monohydroxyalkyl groups containing from 1 to 3 carbon atoms.
  • the arrow in the formula is a conventional representation of a semi-polar bond.
  • suitable phosphine oxides are:
  • dimethyldodecylphosphine oxide dimethyltetradecylphosphine oxide, ethylmethyltetradecylphosphine oxide, cetyldimethylphosphine oxide, dimethylstearylphosphine oxide, cetylethylpropylphosphine oxide, diethyldodecylphosphine oxide, diethyltetradecylphosphine oxide,
  • RRS O Dialkyl sulfoxides corresponding to the following formula, RRS O, wherein R is an alkyl, alkenyl, betaor gamma-monohydroxyalkyl radical or an alkyl or betaor gamma-monohydroxyalkyl radical containing one or two other oxygen atoms in the chain, the R groups ranging from 10 to 18 carbon atoms in chain length, and wherein R is methyl or ethyl.
  • suitable sulfoxide compounds are:
  • Ampholytic synthetic detergents can be broadly described as derivatives of aliphatic 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 one contains an anionic water solubilizing group. Examples of compounds falling within this definition are sodium-3-dodecylaminopropionate and sodium-3dodecylaminopropanesulfonate.
  • Zwitterionic synthetic detergents can be broadly described as derivatives of aliphatic quarternary ammonium compounds 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 one contains an anionic water solubilizing group.
  • Examples of compounds falling Within this definition are 3-(N,N-dimethyl-Nhexadecylammonio)propane-l-sulfonate and 3-(N,N-dimethyl-N-hexadecylammouio)-2-hydroxypropane-l-sulfonate which are especially preferred for their excellent cool water detergency characteristics.
  • anionic, nonionic, ampholytic and zwitterionic detergent surfactants mentioned above can be used singly or in combination in the practice of the present invention.
  • the above examples are merely specific illustrations of the numerous detergents which can find application within the scope of this invention.
  • organic detergent surfactant compounds can be formulated into any of the several commercially desirable composition forms for example, granular, flake, liquid and tablet forms.
  • a granular detergent composition can contain a polyelectrolyte builder of this invention and a detergent surfactant in the weight ratio of about 1:3 to about 10:1.
  • the preferred ratio of builder to surfactant is about 1:2 to about :1.
  • Another embodiment of this invention is a built liquid detergent composition containing a polyelectrolyte builder described above and a detergent surfactant in a weight ratio of builder to detergent of about 1:3 to about :1.
  • the prefer-red ratio for built liquid compositions of polyelectrolyte builder to detergent is about 1:2 to about 3: 1.
  • the detergent compositions described by this invention employing a polyelectrolyte builder compound as defined above can have special applicability in the area of built liquid detergents.
  • This area presents special problems to the formulator in view of the peculiarities inherent in aqueous systems and the special requirements of solubility of the ingredients and, more especially their stability in such mediums.
  • sodium tripolyphosphate while outstanding in its behavior in granular compositions, is generally regarded as being unsuited for built liquid detergents. It has a strong propensity to hydrolyze into lower forms of phosphates.
  • alkali metal pyrophosphates such as K P O in order to prepare a built liquid detergent. This has been true notwithstanding the known inferiority of pyrophosphates to sodium tripolyphosphate in some compositions, for example, as a builder for heavy duty detergency.
  • a sample built detergent composition of this invention can consist essentially of a polyelectrolyte builder as defined herein and an organic detergent surfactant in the ratios described above and the balance being a vehicle medium, for example, water, a water-alcohol mixture, liquid nonionic surfactant compounds, etc.
  • a finished detergent formulation of this invention there will often be added in minor amounts materials which make the product more effective or more attractive.
  • Soluble sodium carboxymethylcellulose can be added in minor amounts to inhibit soil redeposition.
  • a tarnish inhibitor such as benzotriazole or ethylenethiourea can also be added in amounts up to about 2%.
  • Fluorescers, perfume and color, while not essential in the compositions of the invention, can be added in amounts up to about 1%.
  • An alkaline material or alkali such as sodium hydroxide or potassium hydroxide can be added in minor amounts as supplementary pH adjusters.
  • suitable additives water, brightening agents, bleaching agents, sodium sulfate, and sodium carbonate.
  • Corrosion inhibitors generally are also added.
  • Soluble silicates are highly effective inhibitors and can be added to certain formulas of this invention at levels of from about 3% to about 8%.
  • Alkali metal, preferably potassium or sodium, silicates having a weight ratio of SiO :M O of from 1:1 to 28:1 can be used. M in this ratio refers to sodium or potassium.
  • a sodium silicate having a ratio of SiO :Na O of about 1.6:1 to 2.45:1 is especially preferred for economy and effectiveness.
  • a hydrotropic agent may at times be found desirable.
  • Suitable hydrotropes are water soluble alkali metal salts of toluenesulfonate, benzenesulfonate, and xylenesulfonate.
  • the preferred hydrotropes are the potassium or sodium toluenesulfonates.
  • the hydrotrope salt may be added if so desired, at levels of 0% to about 12%. While a hydrotrope will not ordinarily be found necessary, it can be added if so desired.
  • the specific action of the builders of this invention will vary to some extent, of course, depending upon the ratio of active detergent to builder mixture in any given detergent composition. There will be considerable variation in the strengths of the washing solutions employed by different users, i.e., some users may tend to use less or more of the detergent compositions than will others. Moreover, there will be variations in temperature and in soil loads as between different washing operations. Further the degree of hardness of the water used to make up the washing solutions will also bring about apparent differences in the cleaning power and whiteness maintenance results. Finally, different fabrics will respond in somewhat dilferen-t ways to different detergent compositions. The best type of detergent composition is one which accomplishes an excellent cleaning and whiteness maintenance effect under the most diverse cleaning conditions. The built detergent compositions of this invention are valuable in this respect.
  • the sodium poly(i-taconate-acrylate) builder in Example I can be replaced at an equal percentage basis by sodium salts of: a 1:1 copolymer of ethylene and itaiconic acid with an equivalent weight of 79; a 1:1 copolymer of propylene and maleic acid with an equivalent weight of 79; a 1:4 copolymer of 3-butenoic acid and maleic acid with an equivalent weight of 61.1; a 1:9 copolymer of isocrotonic acid and citraconic acid with an equivalent weight of 66.2; a 121.9 copolymer of methacrylic acid and aconitic acid with an equivalent weight of 62.2; a 1.211 copolymer of 4-pentenoio acid and itaconic acid, with an equivalent weight of 78.3, said equivalent weights calculated as
  • EXAMPLE II Another excellent granular detergent composition has the following ingredients.
  • Trichlorocarbanilide .7 Sodium poly(itaconate-aconitate) (1:1 on molar basis) (specific viscosity of 1% by weight in dimethylformamide at room temperature .12;
  • Sodium poly(it-aconate-rn'aleate), sodium poly(mesaconate-fumerate) and sodium poly(methylenemalonatecitraconate) copolymers can each be used as a builder in the above formula in place of the sodium poly(itaconateaconitate) copolymer of Example 111. These sodium salts have equivalent weights and viscosities comparable to the copolymer of Example 111.
  • EXAMPLE IV An especially effective and eificient granular detergent composition according to this invention has the following composition.
  • EXAMPLE V An excellent built liquid detergent composition according to this invention has the following composition.
  • Percent Sodium dodecylbenzenesulfonate (the dodecyl radical being a polypropylene, predominantly tetrapropylene averaging 12 carbon atoms) 6.0 Dimethyldodecylamine oxide 6.0 Monoethanolammonium polymaleate (specific viscosity of 1% by weight in dimethylformamide at room temperature .21; equivalent weight 58) 20.0 Potassium toluenesulfonate 8.0 Sodium silicate (SiO :Na O of 2.45: 1) 3.8 Carboxymethyl hydroxyethyl cellulose 0.3 Water Balance This composition performs equally well in laundry usage as well as dishwashing usage. The 'builders resistance to hydrolysis allows longer shelf life, a feature not found with sodium tripolyphosphate built liquid compositions.
  • EXAMPLE VII Another effective cool water heavy duty built granular composition consists of the following ingredients.
  • the sodium polyitaconate builder of Example VII can be replaced by water-soluble salts of: poly(maleic acid), poly(mesaconic acid), poly(furnaric acid), poly(methylenemalonic acid) or poly(citraconic acid) with equally good results, said salts having equivalent weights and viscosities comparable to the builder of Example VII.
  • An excellent built liquid composition of this invention has the following ingredients.
  • EXAMPLE IX tive the dodecyl group being derived from tetrapropylene. This active will be referred to as ABS which is widely used in commercially available detergent compositions.
  • ABS which is widely used in commercially available detergent compositions.
  • the wash-wear tests involved washing naturally soiled Shirts carryjects under ordinary conditions for two normal working days. Following wearing, the collars and cuffs were washed for minutes in a small agitator-type machine using solutions of the detergent compositions to be evaluated. The washing conditions were as hereinafter specified. After a washing and drying cycle the collars and cuffs washed by a composition being evaluated were visu- 14 terminations and this type of grading scheme was to establish the relative builder performance of several compounds of this invention as compared to a known accepted standard in the detergent industry, i.e., sodium tripolyphosphate.
  • the washing solutions used in these white shirt detergency tests contained .03% by weight active detergent compound, in each instance ABS, and a representative polyelectrolyte builder at concentration levels ranging fro-m .03% to .06% by weight. No fluorescers, bleaches or anti-redeposition agents were used so as not to mask the builder properties.
  • the washing solution was standardized to a pH of 10 and the water used contained 7 grams per gallon hardness. Temperature of washing solution was 140 F.
  • the cleaning grades obtained with such polyelectrolyte builder compounds as sodium polymaleate, sodium polyitaconate, sodium (itaconate-acrylate) copolymer, and sodium (itaconate-aconitate) copolymer were substantially better relatively, than the cleaning grades of sodium tripolyphosphate.
  • polyelectrolyte polymeric builder compounds of this invention which were tested in the manner described above and for which performance data is presented in FIGURE 1 had the following properties and characteristics.
  • the specific viscosity figures given below were obtained by using a conventional Cannon-Fenske flow-type viscometer under the specific conditions mentioned in the footnotes of Table I.
  • the two graph lines at the lower right hand quadrant of the figure are samples of polyelectrolyte aliphatic polycarboxyli-c compounds which do not meet the specific essential structural requirements set forth previously for desirable builder characteristics. From the formulas below, it will be seen that they contain interfering branch groups which boost their equivalent weights outside of the required range.
  • Sodium poly(vinylmethylether/maleate) has the following structure:
  • FIGURE 1 clearly shows their inferior performance as detergency builders and such compounds are clearly excluded from this invention.
  • Points identified as A, B, C, and D represent cleaning grades scored by additional built compositions using different samples of builder compounds at builder concentrations of .O3% and .06%.
  • Points A, B and D represent cleaning levels accomplished by sodium polyitaconate-built ABS detergent compositions wherein the sodium polyitaconate builder compounds had specific viscosities different from the previous sample as seen from Table 1.
  • Point C represents a cleaning grade achieved by an additional evaluation of a different sample of sodium (ethylene-maleate) linear copolymer, also at a .03% builder concentration with ABS.
  • polyelectrolyte builder compounds of this invention Another of the many advantages offered by the polyelectrolyte builder compounds of this invention is the surprising discovery that they are less corrosive to aluminum and other metals than known builder compounds.
  • a cleansing and laundering composition comprising (1) an organic water-soluble detergent surfactant selected from the group consisting of anionic, nonionic, zwitterionic, and ampholytic deterent surfactants, and mixtures thereof, and (2) a polyelectrolyte builder material consisting of water-soluble salts of a polymeric aliphatic polycarboxylic acid selected from the group consisting of (a) water-soluble salt of the homopolymer of an aliphatic polycarboxylic acid having thefollowing empirical formula:
  • X, Y, and Z are each selected from the group consisting of hydrogen, methyl, carboxyl, and car'boxymethyl, at least one of X, Y, and Z being selected from the group consisting of carboXyl and carboxymethyl, provided that X and Y can 'be carboxy methyl only when Z is selected from carboxyl and carboxymethyl, wherein only one of X, Y, and Z can be methyl, and wherein n is a whole integer having a value within a range, the lower limit of which is three and the upper limit of which is determined by the solubility characteristics in an aqueous system;
  • R is selected from the group consisting of hydrogen, methyl, carboxyl, carboxy- 'rneth'yl, and carboxyethyl; wherein only one R can be methyl; wherein m is at least 45 mole percent of the copolymer; wherein X, Y, and Z are each selected from the group consisting of hydrogen, methyl, carboxyl, and carboxymethyl, at least one of X, Y, and Z being selected from the group of carboxyl and carboxy-methyl provided that X and Y can be carboxymethyl only when Z is selected from carboxyl and carboxymethyl, wherein only one of X, Y and Z can be methyl; and wherein n is a whole integer within a range, the lower limit of which is three and the upper limit of which is determined primarily by the solubility characteristics in an aqueous system; said polyelectrolyte builder material having a minimum molecular weight of 350 calculated as the acid form and an equivalent weight of about 50 to about 80, calculated as
  • X, Y and Z are each selected from the group consisting of hydrogen, methyl, carboxyl and carboxymethyl, at least one of X, Y and Z being selected from the group consisting of carboxyl and carboxymethyl, provided that X and Y can be carboxymethyl only when Z is selected from carboxyl and carboxymet-hyl, wherein only one of X, Y and Z can be methyl, and wherein n is a whole integer having a value within the range the lower limit of which is three and the upper limit of which is determined primarily by the solubility characteristics in an aqueous system, said polyelectrolyte builder material having a minimum molecular weight of 350 calculated as the acid form and an equivalent weight of about 50 to about 80 calculated as the acid form, the ratio of said polyelectrolyte builder to said detergent surfactant being in the range of from about 1:3 to about :1, by weight.
  • a cleansing and laundering composition comprising (1) an organic water soluble detergent surfactant selected from the group consisting of anionic, nonionic, zwitterionic, and ampholytic detergent surfactants, and mixtures thereof, and (2) as a polyelectrolyte builder material, a water-soluble salt of a coplymer of at least two of the monomeric species having the empirical formula described in claim 2, said polyelectrolyte builder material having a minimum molecular weight of 350, calculated as the acid form, and an equivalent weight of about 50 to about 80, calculated as the acid form, the ratio of said polyelectrolyte builder to said detergent surfactant being in the range of from about 1:3 to about 10 :1, by weight. 4.
  • an organic water soluble detergent surfactant selected from the group consisting of anionic, nonionic, zwitterionic, and ampholytic detergent surfactants, and mixtures thereof
  • a polyelectrolyte builder material a water-soluble salt of a coplymer of at least two
  • a cleansing and laundering composition comprising (1) an organic water soluble detergent surfactant selected from the group consisting of anionic, nonionic, zwitterionic, and ampholytic detergent surfactants and mixtures thereof, and (2) as a polyelectrolyte builder material, a water-soluble salt of a copolymer of a member selected from the group of alkylenes and monocarboxylic acids with the aliphatic polycarboxylic compounds described in claim 2, said copolymers having the general formula:
  • R is selected from the group consisting of hydrogen, methyl, carboxyl, carboxyrnethyl, and carboxyethyl, wherein only one R can be methyl;
  • m is at least 45 mole percent of the copolymer, wherein X, Y and Z are each selected from the group consisting of hydrogen, methyl, carboxyl and carboxymethyl, at least one of X, Y and Z being selected from the group consisting of carboxyl and carboxymethyl provided that X and Y can be carboxymethyl only when Z is selected from carboxyl and carboxymethyl, wherein only one of X, Y and Z can be methyl; wherein n is a whole integer Within a range, the lower limit of which is three and the upper limit of which is determined primarily by the solubility characteristics in an aqueous system, said polyelectrolyte builder material having a minimum molecular weight of 350, calculated as the acid form, and an equivalent weight of about 50 to about 80, calculated as the acid form, the ratio of said polyelectrolyte builder to said detergent surfactant being in the range of from about 1:3 to about 10:1, by weight.
  • a built liquid composition of claim 1 wherein the ratio of the polyelectrolyte builder to the detergent surfactant is from about 1:2 to about 3:1, by weight.
  • a cleansing and laundering composition comprising as a detergent surfactant an anionic water-soluble alkali metal salt of an organic sulfuric reaction product having in its molecular structure an alkyl radical having from 8 to 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals, and a builder compound as defined in claim 1, the ratio of said builder compound to said detergent surfactant being in the range of from about 1:3 to about 10:1, by weight, and said composition providing in aqueous solution a pH between about 9 and about 12.
  • a copolymer selected from the group consisting of (itaconic acid and aconitic acid) copolymer (itaconic acid and maleic acid) copolymer, (mesaconic acid and fumaric acid) copolymer and (methylenemalonic acid and citronic acid) copolymer.
  • a cleansing and laundering composition comprising 3-hydroxy-4-decoxybutyl methyl sulfoxide as a detergent surfactant and a sodium polymaleate builder compound, said polymaleate builder compound having a minimum molecular weight of 350, calculated as the acid form, and an equivalent Weight of about 50 to about 80, calculated as the acid form, the ratio of said builder to said detergent surfactant being from about 1:3 to about 10:1, by weight.

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US269359A 1963-04-01 1963-04-01 Polyelectrolyte builders and detergent compositions Expired - Lifetime US3308067A (en)

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Application Number Priority Date Filing Date Title
US269359A US3308067A (en) 1963-04-01 1963-04-01 Polyelectrolyte builders and detergent compositions
AU41946/64A AU293474B2 (en) 1963-04-01 1964-03-11 Polyelectrolyte builders and detergent compositions
FI0537/64A FI42739B (de) 1963-04-01 1964-03-13
GB1285864A GB1054755A (en) 1963-04-01 1964-03-26 Polyelectrolyte builders and detergent compositions
DE19641467656 DE1467656B2 (de) 1963-04-01 1964-03-28 Polyelektrolyt-aufbaustoffe fuer wasch- und reinigungsmittel
FR969267A FR1476512A (fr) 1963-04-01 1964-03-31 Adjuvants polyélectrolytes de détergence et compositions détergentes
AT277164A AT278215B (de) 1963-04-01 1964-03-31 Reinigungs- und Waschmittelzusammensetzung
CH410964A CH490491A (de) 1963-04-01 1964-04-01 Reinigungs- und Waschmittel
DK161064AA DK119268B (da) 1963-04-01 1964-04-01 Rense- og vaskemiddelblandinger indeholdende buildere.
SE04013/64A SE328362B (de) 1963-04-01 1964-04-01
NL6501871A NL132878C (nl) 1963-04-01 1965-02-15 Werkwijze voor het bereiden van een was- of reinigingsmiddel
BE685413D BE685413A (de) 1963-04-01 1966-08-11

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US269359A US3308067A (en) 1963-04-01 1963-04-01 Polyelectrolyte builders and detergent compositions
NL6501871A NL132878C (nl) 1963-04-01 1965-02-15 Werkwijze voor het bereiden van een was- of reinigingsmiddel
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CH (1) CH490491A (de)
DE (1) DE1467656B2 (de)
DK (1) DK119268B (de)
FI (1) FI42739B (de)
FR (1) FR1476512A (de)
GB (1) GB1054755A (de)
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SE (1) SE328362B (de)

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DE1467656A1 (de) 1969-10-23
SE328362B (de) 1970-09-14
FI42739B (de) 1970-06-30
DK119268B (da) 1970-12-07
AU293474B2 (en) 1969-08-19
NL6501871A (nl) 1966-08-16
CH490491A (de) 1970-05-15
AT278215B (de) 1970-01-26
AU4194664A (en) 1966-09-08
BE685413A (de) 1967-01-16
NL132878C (nl) 1971-07-15
DE1467656B2 (de) 1973-02-22
GB1054755A (en) 1967-01-11
FR1476512A (fr) 1967-04-14

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