US3536628A - Soap compositions - Google Patents

Soap compositions Download PDF

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Publication number
US3536628A
US3536628A US515738A US3536628DA US3536628A US 3536628 A US3536628 A US 3536628A US 515738 A US515738 A US 515738A US 3536628D A US3536628D A US 3536628DA US 3536628 A US3536628 A US 3536628A
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United States
Prior art keywords
soap
acid
composition
sodium
ethylene oxide
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Expired - Lifetime
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US515738A
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English (en)
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Frank Lancashire
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Procter and Gamble Co
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Individual
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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/365—Organic compounds containing phosphorus containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3839—Polyphosphonic 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
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • 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
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/361—Phosphonates, phosphinates or phosphonites
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/34—Organic compounds, e.g. vitamins containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • This invention relates to soap compositions particularly suitable for use in hard Water.
  • Soap is an excellent detergent, but it has a serious disadvantage.
  • This disadvantage is its tendency to react with the metallic ions which are responsible for the hardness of water, notably calcium and magnesium ions.
  • This reaction forms an insoluble curd, also known as lime soap.
  • This insoluble lime soap forms undesirable deposits on the inside surfaces of washing machines. It is also deposited on fabrics which are washed in hard water with soap as the detergent. These deposits give rise to a poor hand, disagreeable odor and poor color of the washed fabrics. It also reduces the water-absorbency of fabrics, e.g., towels, which have been washed with soap in hard water.
  • a soap composition having improved curd-dispersing properties consists es sentially of from about 40% to about 95% of a higher fatty acid soap; from about 5% to about 60% of a mixture of at least one synthetic detergent selected from the group consisting of (1) a detergent which contains in its molecular structure a zwitterion or a semi-polar bond and (2) an amphoteric synthetic detergent; and at least one watersoluble salt of a phosphonic acid of the general formula:
  • X can be H, OH or carbonyl oxygen
  • Y can be H, OH, CH3, CH2PO3H2
  • the weight ratio of the synthetic detergent to phosphonic acid salt should be from about 1:4 to about 4:1, and preferably from about 1:2 to about 2: 1.
  • the fatty acid soap should comprise from about to about 90% by weight of the detergent composition
  • the synergistic curd dispersing mixture of the synthetic detergent and the phosphonic acid salt should comprise from about 10% to about by weight of the composition.
  • the higher fatty acid soaps suitable for use as the present invention are the sodium, potassium, and the alkylolammonium salts of higher fatty acid (C -C 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, Similarly, palm and palm kernel oil are useful starting materials, as are synthetic fats simulating, for instance, tallow.
  • the synthetic detergents useful in the present invention can be of three types, those which contain in their molecular structure a zwitterion or a serni-polar bond or an amphoteric synthetic detergent.
  • the zwitterionic detergents are aliphatic quarternary ammonium compounds in which one aliphatic substituent contains from about 10 to about 18 carbon atoms and another aliphatic substituent contains a water solubilizing anionic group.
  • examples of such compounds are water salts of alkylated betaines and sultaines of the general formula:
  • R is an alkyl group of from about 10 to about 18 carbon atoms
  • R and R are alkyl groups of from 1 to about 3 carbon atoms
  • R is an alkylene or hydroxy alkylene group of from 1.to about 4 carbon atoms
  • X is a carboxylic acid or sulphonic acid anion.
  • Especially preferred compounds are 3-(N,N-dimethyl-N-alkyl)ammonio 2 hydroxy propane l sulphonates and 3- (N,N-dimethyl N alkyl)ammonio-propane-l-sulfonates in which the alkyl group contains from about 10 to about 18 carbon atoms and preferably 12 to 16.
  • Useful synthetic detergents which contain semi-polar bonds are tertiary amine oxides of the general formula R R R N O and tertiary phosphine oxides of the general formula R R R P- O where R is an alkyl, alkenyl, or hydroxy alkyl radical of from about 10 to about 18 carbon atoms and R and R are each alkyl or monohydroxy alkyl radicals of from 1 to about 3 carbon atoms; for example, dimethyl dodecyl amine oxide, diethanol dodecyl amine oxide, dimethyl decyl amine oxide, dimethyl tetradecyl amine oxide, or dodecyl bis (hydroxymethyl)phosphine oxide, tetradecyl dimethyl phosphine oxide, dimethyl dodecyl phosphine oxide; and sulfoxides of the general formula R R S O in which R; is an alkyl, alkenyl, hydroxy alkyl or alkoxy alkyl radical of from about to about
  • amphoteric synthetic detergents which are suitable for use in the compositions of the invention are synthetic detergents which contain both an acidic and a basic function in their structure.
  • the acidic group can be a carboxylic, sulfuric, sulfonic or phosphoric acid group and the basic group contains a non-quaternary nitrogen atom.
  • suitable amphoteric synthetic detergents are synthetic detergents which contain both an acidic and a basic function in their structure.
  • the acidic group can be a carboxylic, sulfuric, sulfonic or phosphoric acid group and the basic group contains a non-quaternary nitrogen atom.
  • R represents an alkyl radical of from about 10 to about 18 carbon atoms.
  • the preferred amphoteric synthetic detergent is the sodium salt of N-la'uryl-beta-alanine.
  • the phosphonic acid salts which are suitable for use in the compositions of the invention are the alkali metal salts of ethane-l-hydroxy-1,1-diphosphonic acid; ethane-Z-carboxy-1,1-diphosphonic acid; hydroxymethanediphosphonic acid; ethane-2,1,1-triphosphonic acid; carbonyldiphosphonic acid; and propane-1,1,3,3-tetraphosphonic acid; propane-1,1,2,3-tetraphosphonic acid; and propane-1,2,2-3-tetraphosphonic acid.
  • the preferred phosphonic acid salt is the trisodium salt of ethane-l-hydroxy-l,l-diphosponic acid.
  • Some of the aforementioned zwitterionic, semi-polar, or amphoteric surface active agents have some limited lime soap dispersing power. According to this discovery, this power is synergistically increased to a surprising degree by the admixture in certain amounts of the specified phosphonate salts, which themselves have limited lime soap dispersing power. This synergistic increase in the lime soap dispersing power is illustrated by the following tests:
  • the 3-hydroxy-4-decoxybutylmethyl sulfoxide compound can be replaced by dodecydimethyl amine oxide or dodecyldimethyl phosphine oxide, and equally excellent curd disperising properties are obtained.
  • the EHDP can be replaced in whole or in part by the sodium or potassium salts of ethane-2- carboxy-1,1-diphosphonic acid, hydroxymethanediphosphonic acid, ethane-2,1,l-triphosphonic acid, carbonyldiphosphonic acid or propane-1,1,3,3-tetraphosphonic acid.
  • compositions of the invention may be produced in any conventional form such as bars, tablets, powders, liquids or pastes, the invention is particularly suitable for granular washing compositions such as are used for domestic laundering.
  • Such compositions preferably contain at least 40% by weight of soap, and may additionally contain other usual ingredients of household washing compositions.
  • alkaline builder salts e.g., sodium carbonate and sodium silicate
  • peroxy bleaching agents e.g., sodium perborate
  • optical whitening agents e.g., sodium perborate
  • compositions of the invention are that solutions of the compositions do not suds appreciably until all the hardness of the water has been destroyed and the solution contains sufficient free soap to have effective washing power. This delayed sudsing avoids under-usage of the composition.
  • sudsing of the solution is often produced before the concentration of free soap in the solution has become high enough to give effective detergency. This premature sudsing may cause the user of the composition to add insufficient amounts of composition to the washing solution. Poor cleaning will be the result of this insufficient addition.
  • This problem can be avoided by means of the use of the compositions of the invention, since they do not suds significantly until sufficient soap for effective washing is present.
  • compositions of the invention give effective lime soap dispersion during the washing stage. If the Washed goods are rinsed in hard water, the washing solution remaining in the fabric is diluted by a large proportion of the added hard water. Under these conditions, some lime soap in undispersed form may be formed. According to a further feature of the invention, the tendency for this to happen can be reduced or entirely eliminated by including in the soap composition a low-sudsing nonionic detergent. Moreover, low-sudsing nonionic detergent. Moreover, low-sudsing nonionic detergents are used to avoid the appearance of suds in the rinse water.
  • the polyethylene oxide condensates of alkyl phenols and dialkyl 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 about to 30 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.
  • Alkylene oxide-containing nonionic detergents derived from the condensation of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine.
  • a series of compounds are contemplated whose characteristics can be controlled by achieving a desired balance between the hydrophobic and hydrophilic elements.
  • the coconut alcohol fraction which is preferred is a distilled coconut alcohol having from 10 to 1-6 carbon atoms, with the approximate chain length distribution being from 2% C 66% C12, 23% C and 9% C
  • Another preferred compound is the condensation product of tallow derived alcohol and from about 3 to about 15 moles of ethylene oxide per mole of tallow alcohol; a specific illustration being the condensation reaction product of one mole of tallow alcohol and 4 moles of ethylene oxide (TE (4)
  • TE (4) A well known class of alkylene oxide-containing nonionic synthetic detergents of this type 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.
  • the preferred nonionic detergent is the condensation product of one mole of hydrogenated tallow fatty alcohol with 4 moles of ethylene oxide.
  • the proportion of low sudsing nonionic detergent in the composition may be up to about 20% by weight of the soap content, and preferably from at least about 2% to about 15%, by weight of the soap content of the composition.
  • the product of each example gives no suds below the concentration at which all the hardness has been removed and the soap concentration is etfective for washing.
  • the washing solution is free from lime soap scum and no deposit of lime soap is left in the washing machine.
  • the rinse water is free from lime soap scum and also free from suds.
  • N-lauryl-beta-al-anine salt is replaced by the sodium salt of N-alkyl glycine in which the alkyl radical is derived from coconut oil and if the ethane-l-hydroxy-l,l-diphosphonic acid trisodium salt is replaced by sodium salts of the other phosphonic acids named above.
  • a soap composition is prepared to give the following product composition:
  • a soap composition is prepared to give the following production composition:
  • a soap composition is prepared to give the following product composition:
  • a spray-dried granular composition is prepared to give the following finished product composition:
  • Germicidal agents can be added to the soap compositions of the present invention to render the products antiseptic in quality.
  • the invention described hereinabove represents a substantial improvement over prior art practices according to which attempts were made to solve the problem of curd dispersion by the adidtion of sequestering agents to soap.
  • One especially troublesome problem was that which arose from the use of soap detergent compositions in washing machines and boilers which contained internal heating coils to warm the water. The lime soap and curd tends to form deposits on these heating elements and eventually seal them 01f.
  • One prior art solution to this problem called for admixing soap with about 5% by weight of the soap of an alkali metal salt of certain diphosphonic acids such as ethane-1-hydroxy-1,1-diphosphonic acid and ethane- 1,1,2-triphosphonic acid.
  • sodium nitrilotriacetate was suggested for the same purpose as the just mentioned polyphosphonic acids.
  • a soap composition having improved curd-dispersing properties consisting essentially of (I) from about 40% to about 95% of a higher fatty acid soap;
  • a soap composition according to claim 1 containing from about 45% to about 90% by weight of said higher fatty acid soap; from about to about 55% by weight of said synergistic mixture of synthetic detergent and phosphonic acid salt, and in which the ratio, by weight, of said synthetic detergent to said phosphonic acid salt is from about 1:2 to about 2: l.
  • composition of claim 1 which also contains up to about 20% by weight of the soap content of an alkylene oxide containing nonionic synthetic detergent.
  • composition of claim 4 which contains from about 2% to about 15% of said nonionic synthetic detergent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
US515738A 1965-12-22 1965-12-22 Soap compositions Expired - Lifetime US3536628A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US51573865A 1965-12-22 1965-12-22

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US3536628A true US3536628A (en) 1970-10-27

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US (1) US3536628A (forum.php)
BE (1) BE703312A (forum.php)
DE (1) DE1617180B2 (forum.php)
GB (2) GB1103590A (forum.php)
NL (1) NL6712340A (forum.php)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3956158A (en) * 1974-01-07 1976-05-11 Lever Brothers Company Pourable liquid compositions
US4083972A (en) * 1973-06-19 1978-04-11 The Procter & Gamble Company Compositions for inhibiting anomalous deposition and mobilization of calcium phosphate in animal tissue
US4154694A (en) * 1973-01-19 1979-05-15 Lever Brothers Company Detergent compositions
US4155871A (en) * 1973-01-19 1979-05-22 Lever Brothers Company Detergent compositions
EP0025242A1 (en) * 1979-09-07 1981-03-18 Procter & Gamble European Technical Center Soap bars
US4288225A (en) * 1979-08-18 1981-09-08 Henkel Kommanditgesellschaft Auf Aktien Fluid, cold-stable, two-component washing compositions and method of washing textiles
US5002686A (en) * 1988-09-01 1991-03-26 Ciba-Geigy Corporation Aqueous, hard water-resistant wetting agent and detergent composition, and the preparation and use thereof in textile pretreatment
US5391315A (en) * 1991-09-27 1995-02-21 Ashkin; Abraham Solid cake detergent carrier composition
US5891834A (en) * 1995-09-19 1999-04-06 Colgate Palmolive Company Composition
US5957819A (en) * 1997-11-17 1999-09-28 Cortesi; Gary A. Golf exercise device

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3635661B2 (ja) * 1993-03-30 2005-04-06 味の素株式会社 洗浄剤組成物

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB775364A (en) * 1954-05-05 1957-05-22 Unilever Ltd Improvements in soap compositions
GB943628A (en) * 1960-05-24 1963-12-04 Unilever Ltd Soap compositions
US3159581A (en) * 1962-04-13 1964-12-01 Procter & Gamble Detergency composition
US3214454A (en) * 1958-09-06 1965-10-26 Henkel & Compagnie G M B H Process of forming metal ion complexes
US3290254A (en) * 1961-10-25 1966-12-06 Chevron Res Methyl-beta-hydroxydodecyl sulfoxide containing detergent compositions
US3297578A (en) * 1963-07-26 1967-01-10 Monsanto Co Bleaching, sterilizing, disinfecting, and deterging compositions
US3318817A (en) * 1965-07-16 1967-05-09 Procter & Gamble Process for preparing detergent tablets
US3368978A (en) * 1964-12-28 1968-02-13 Monsanto Co Builder compositions and detergent compositions using same
US3382180A (en) * 1958-04-01 1968-05-07 Lever Brothers Ltd Detergent compositions containing sulfoxide as a suds-stabilizing agent
US3392121A (en) * 1962-11-05 1968-07-09 Procter & Gamble Built detergent compositions
US3400148A (en) * 1965-09-23 1968-09-03 Procter & Gamble Phosphonate compounds
US3422021A (en) * 1963-03-18 1969-01-14 Procter & Gamble Detergent composition

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB775364A (en) * 1954-05-05 1957-05-22 Unilever Ltd Improvements in soap compositions
US3382180A (en) * 1958-04-01 1968-05-07 Lever Brothers Ltd Detergent compositions containing sulfoxide as a suds-stabilizing agent
US3214454A (en) * 1958-09-06 1965-10-26 Henkel & Compagnie G M B H Process of forming metal ion complexes
GB943628A (en) * 1960-05-24 1963-12-04 Unilever Ltd Soap compositions
US3290254A (en) * 1961-10-25 1966-12-06 Chevron Res Methyl-beta-hydroxydodecyl sulfoxide containing detergent compositions
US3159581A (en) * 1962-04-13 1964-12-01 Procter & Gamble Detergency composition
US3392121A (en) * 1962-11-05 1968-07-09 Procter & Gamble Built detergent compositions
US3422021A (en) * 1963-03-18 1969-01-14 Procter & Gamble Detergent composition
US3297578A (en) * 1963-07-26 1967-01-10 Monsanto Co Bleaching, sterilizing, disinfecting, and deterging compositions
US3368978A (en) * 1964-12-28 1968-02-13 Monsanto Co Builder compositions and detergent compositions using same
US3318817A (en) * 1965-07-16 1967-05-09 Procter & Gamble Process for preparing detergent tablets
US3400148A (en) * 1965-09-23 1968-09-03 Procter & Gamble Phosphonate compounds

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4154694A (en) * 1973-01-19 1979-05-15 Lever Brothers Company Detergent compositions
US4155871A (en) * 1973-01-19 1979-05-22 Lever Brothers Company Detergent compositions
US4083972A (en) * 1973-06-19 1978-04-11 The Procter & Gamble Company Compositions for inhibiting anomalous deposition and mobilization of calcium phosphate in animal tissue
US3956158A (en) * 1974-01-07 1976-05-11 Lever Brothers Company Pourable liquid compositions
US4288225A (en) * 1979-08-18 1981-09-08 Henkel Kommanditgesellschaft Auf Aktien Fluid, cold-stable, two-component washing compositions and method of washing textiles
EP0025242A1 (en) * 1979-09-07 1981-03-18 Procter & Gamble European Technical Center Soap bars
US5002686A (en) * 1988-09-01 1991-03-26 Ciba-Geigy Corporation Aqueous, hard water-resistant wetting agent and detergent composition, and the preparation and use thereof in textile pretreatment
US5391315A (en) * 1991-09-27 1995-02-21 Ashkin; Abraham Solid cake detergent carrier composition
US5891834A (en) * 1995-09-19 1999-04-06 Colgate Palmolive Company Composition
US5957819A (en) * 1997-11-17 1999-09-28 Cortesi; Gary A. Golf exercise device

Also Published As

Publication number Publication date
DE1617180B2 (de) 1974-10-31
DE1617180A1 (de) 1971-02-18
NL6712340A (forum.php) 1969-03-11
GB1103590A (en) 1968-02-14
GB1103578A (en) 1968-02-14
BE703312A (forum.php) 1968-02-29

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