US3140261A - Detergent composition - Google Patents

Detergent composition Download PDF

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Publication number
US3140261A
US3140261A US152015A US15201561A US3140261A US 3140261 A US3140261 A US 3140261A US 152015 A US152015 A US 152015A US 15201561 A US15201561 A US 15201561A US 3140261 A US3140261 A US 3140261A
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United States
Prior art keywords
alkyl
weight
carbon atoms
phenol
alkylene oxide
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Expired - Lifetime
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US152015A
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English (en)
Inventor
Reginald W Noad
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Shell USA Inc
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Shell Oil Co
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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
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • C11D1/8305—Mixtures of non-ionic with anionic compounds containing a combination of non-ionic compounds differently alcoxylised or with different alkylated chains

Definitions

  • the detergent composition comprises a major proportion by weight of a mono alkyl aryl sulphonate in which the alkyl group containsat least 8 carbon atoms or a di-alkyl aryl sulphonate in which one of the alkyl groups is methyl and the other alkyl group contains at least 8 carbon atoms, and a minor proportion by weight of (i) an alkyl aryl sulphonate in which the or each alkyl group contains less than 8 carbon atoms (and preferably in which the sum of carbon atoms in the alkyl groups is less than 8) or an aryl sulphonate, (ii) a phenol-alkylene oxide condensate, an alcohol-alkylene oxide condensate or a mercaptan-alkylene oxide condensate having an average of not more than 11 alkylene oxide units per molecule, and (iii) a phenolalkylene oxide condensate, an alcohol-alkylene oxide condensate, an
  • the monoor di-alkyl aryl sulphonate which constitues the major proportion by weight of the detergent composition is preferably a sulphonic acid or a salt thereof, of an alkylated benzene or toluene, although those of naphthalene may equally well be used.
  • the salts may for example be alkali metal such as sodium or potassium salts, orbe ammonium or alkanolamine salts.
  • sulphonates of this type are the alkali metal salts of sulphonic acids such as are obtained by alkylating benzene or toluene, with an alkylating agent having preferably between eight and sixteen carbon atoms inclusive per molecule, for an example an olefin, an olefin polymer or alkyl halide, and converting the alkyl aromatic hydrocarbon thus formed into the corresponding mono-sulphonic acid.
  • the sulphonic acids may then be readily neutralised by. adding for example alkali metal hydroxide or alkali metal carbonate to form the corresponding salts.
  • Suitable sulphonates include monoand poly-propyl, butyl, amyl or heptyl benzene sulphonates, propylated naphthalene sulphonates or butylated diphenyl sulphonates.
  • the alkyl aryl sulphonic acid salts, particularly 3,146,261 Patented July 7, 1964 alkali metal or ammonium salts are preferred e.g. the
  • V potassium xylene sulphonates or sodium toluene sulphonates V potassium xylene sulphonates or sodium toluene sulphonates.
  • the aryl sulphonates may be obtained by sulphonation of the aryl hydrocarbon e.g. by sulphonation of benzene or naphthalene to form a benzene or naphthalene sulphonate.
  • the sulphonic acids thereby formed may be neutralised to form the corresponding salts, e.g. alkali metal, ammonium or alkanol-amine salts. Examples of such salts are sodium or potassium benzene sulphonates.
  • the desired blend of sulphonates may be prepared by sulphonating directly a mixture of short chain alkylated aryl hydrocarbon or aryl hydrocarbon with the longer chain monoor di-alkyl aryl hydrocarbon.
  • a mixture of straight chain (C to C mono alkyl hydrocarbon and xylene or toluene may be sulphonated using for example S0 in a SO /a1kylate mole ratio about 3:1.
  • alkylene oxide/phenol, alkylene oxide/ alcohol or alkylene oxide/mercaptan condensates used in compositions of the present invention may be derived from any alkylene oxide, but preferably from alkylene oxides containing between two and four carbon atoms in the molecule inclusive.
  • the preferred alkylene oxides are ethylene oxide or 1,2-propylene oxide.
  • Other suitable alkylene oxides are 1,2- and 2,3-butylene oxides, and isobutylene oxide. Any method suitable for the preparation of these condensates can be used, and one such method is deand subsequently treating with a lower aliphatic alcohol or glycol and removing the suspended solid material and the alcohol or glycol from the polyoxyalkylene compound.
  • Alkylene oxide/ phenol and alkylene oxide/ alcohol condensates may also be prepared using mixtures of alkylene oxides.
  • a mixture of ethylene oxide and 1,2-propylene oxide is employed, a polyoxyalkylene compound is formed in which the ethylene oxide and propylene oxide units are distributed randomly throughout the polyoxyalkylene compound in substantially the same proportions as the alkylene oxides are present in the mixture used.
  • One method of making these block copolymers is by condensing an organic compound containing at least one hydroxyl group e.g. a phenol or an alcohol, at an elevated temperature and in the presence of a condensation catalyst, with one or more equivalents of an alkylene oxide.
  • an organic compound containing at least one hydroxyl group e.g. a phenol or an alcohol
  • Suitable condensation catalyst are strong bases, e.g. a quaternary ammomum base or sodium hydroxide, orcompounds such as boron taining an average'of not more than 11 alkylene oxide" units per molecule, and condensates containing an aver-:
  • alkylene oxide units per molecule may be readily prepared.
  • Particularly preferred condensates are respectively, those containing an average of between 7 and 10 moles of alkylene oxide per mole of phenol, alcohol, or mercaptan e.g. an average of 8.5 moles of alkylene oxide per mole of phenol, alcohol or mercaptan, and those containing an average of between 11 and 18 moles of alkylene oxide per mole of phenol, alcohol or mercaptan e.g. an average of 15 moles of alkylene oxide per mole of phenol, alcohol, or mercaptan.
  • the phenols from which the alkylene oxide/phenol condensates are derived include phenol itself, the cresols, resorcinol and the alkyl and dialkyl phenols.
  • Preferred phenols are the alkyl phenols, and these are generally prepared by alkylating phenol with an olefin containing the desired number of carbon atoms.
  • Preferred alkyl phenols are those in which the alkyl group contins between 4 and 10 carbon atoms inclusive, and a particularly preferred alkyl phenol is octyl phenol.
  • Another suitable phenol is dodecyl phenol.
  • the alcohols from which the alkylene oxide/alcohol condensates are derived include monohydric primary, secondary or tertiary alcohols, preferably those having between 6 and 20 carbon atoms inclusive in the molecule and more preferably between 12 and 18 carbon atoms inclusive in the molecule.
  • monohydric primary, secondary or tertiary alcohols preferably those having between 6 and 20 carbon atoms inclusive in the molecule and more preferably between 12 and 18 carbon atoms inclusive in the molecule.
  • aliphatic alcohols for example, lauryl alcohol, cetyl alcohol, oleyl alcohol and 2-ethyl hexanol are used but arylalkyl alcohols, for example benzyl alcohol or the alkyl benzyl alcohols can be used.
  • the mercaptan/alkylene oxide condensates may be derived from primary, secondary, or especially tertiary mercaptans.
  • the mercaptan has between 6 and 20 carbon atoms inclusive per molecule, especially between 12 and 18 carbon atoms inclusive per molecule.
  • the mercaptan may be an aralkyl mercaptan, but aliphatic mercaptans are preferred. Examples of suitable mercaptans are the primary, secondary or tertiary dodecyl or octadecyl mercaptans.
  • Phenol condensates particularly alkyl phenol condensates are preferred to alcohol or mercaptan condensates and the particularly preferred condensates are respectively a condensate of octyl phenol and ethylene oxide containing an average of 8.5 ethylene oxide units per molecule and a condensate of octyl phenol and ethylene oxide containing an average of 15 ethylene oxide units per molecule.
  • the proportion by weight of monoor di-alkylaryl sulphonate may vary provided of course it is a major proportion by weight. However, the preferred proportion by weight is between 55% and 80%, especially between 60% and 70% e.g. about 65%.
  • the proportions of the other components may vary provided they together constitute a minor proportion of the composition of the invention.
  • the proportion by weight of each of the two other components i.e.
  • the alkyl aryl sulphonate in which the or each alkyl group has less than 8 carbon atoms or the aryl sulphonate and the phenol-, alcoholor mercaptan-alkylene oxide condensate having an average of more than 11 alkylene oxide units per molecule is preferably between 1% and 17.5%, particularly between and 12.5% e.g. about 8.5%.
  • additives well-known for this purpose e.g. urea
  • urea may be added to the blend.
  • no more than by weight e.g. about 5% by weight of the detergent active matter, need be added.
  • aqueous solution preferably contains between 20% and 60% by Weight of the detergent composition, for example about 40% by weight.
  • Detergent compositions of the present invention may include the usual builders provided the use of such materials does not adversely affect the desired properties.
  • These builders include for example the water soluble alkali metal phosphates, the polyphosphate salts, sodium silicate, and sodium carboxymethyl cellulose.
  • the builders may be added either before or after dilution of the detergent composition, but preferably after dilution.
  • a detergent composition was prepared by mixing 23.8% by weight of sodium (C to C monoalkyl benzene sulphonates, 3.4% by weight of potassium xylene sulphonate, 7.1% by weight of octyl phenol-ethylene oxide condensate containing an average of 8.5 ethylene oxide units per molecule, and 3.1% by weight of octyl phenol-ethylene oxide condensate containing an average of 15 ethylene oxide units per molecule, the remainder comprising water.
  • This composition was found to have good foam stability as determined in a Dish-Washing Test. It also showed good viscosity/dilution characteristics, and good stability when stored at low temperatures.
  • Na/T sodium toluene sulphonate
  • Na/X sodium xylene sulphonate
  • K/T potassium toluene sulphonate
  • K/X potassium xylene sulphonate.
  • detergent active matter does not include the short chain alkyl aryl sulphonate.
  • Detergent Blend con- Blend conactive taining taining Analysis matter sodium sodium percent toluene xylene wt. sulphonate sulphonate Viscosity, cs. at C 34 291 258 30 229 241 227 224 20 232 184 15 117 68 Clear point, C 34 17.0 2.0 9. 5 -l. 0 25 4.0
  • compositions of the invention especially those containing potassium toluene sulphonate, usually have higher viscosities than those of blends A, B or C above.
  • the compositions of the invention at higher concentrations are not as high as those of blends A, B and C.
  • EXAMPLE V To blends of parts by weight of sodium (C to C monoalkyl benzene sulphonates with 9 parts by weight of octyl phenol-ethylene oxide condensate having an average of 15 ethylene oxide units per molecule, and 21 parts by weight of octyl phenol-ethylene oxide condensate having an average of 8.5 ethylene oxide units per molecule were added 8, 10 or 12 parts by weight of sodium toluene sulphonate.
  • the viscosities and clear points of the resultant blends diluted to different aqueous concentrations were as fol- A blend of 70 parts by Weight of sodium (C to C monoalkyl benzene sulphonates, 27 parts by weight of octyl phenol-ethylene oxide condensate having an average of 8.5 ethylene oxide units per molecule, 3 parts by weight of octyl phenol-ethylene oxide condensate having an average of 15 ethylene oxide units per molecule, and 10 parts by weight of potassium Xylene sulphonate was prepared.
  • This blend was diluted with water to various concentrations and the viscosities determined. 5% and 10% by weight based on the active matter of urea was also added, the corresponding viscosities at different dilutions determined. The clear points at 35% detergent active matter dilutions were also determined.
  • Detergent compositions which have good detergent properties combined with good foaming characteristics and a low critical solution temperature are made by mixing the following components in aqueous solution in the proportions indicated in the following table where the percentages are by weight of the aqueous detergent solution.
  • a detergent composition having good detersive and viscosity dilution properties consisting essentially of water and from to 60% of solute, said solute consisting essentially of (a) 60 to 70% by Weight of alkali metal alkyl aryl sulfonates selected from the group consisting of alkyl benzene sulfonate and alkyl toluene sulfonate having 8 to 13 alkyl carbon atoms,
  • alkali metal alkyl aryl sulfonates selected from the group consisting of toluene sulfonate and xylene sulfonate,
  • a detergent composition having good detersive and viscosity dilution properties consisting essentially of water and from 20 to of solute, said solute consisting essentially of (a) 60 to by Weight of sodium alkyl aryl sulfonates selected from the group consisting of alkyl benzene sulfonate and alkyl toluene sulfonate having 8 to 13 alkyl carbon atoms,

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
US152015A 1960-11-15 1961-11-13 Detergent composition Expired - Lifetime US3140261A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB39185/60A GB949059A (en) 1960-11-15 1960-11-15 Detergent compositions

Publications (1)

Publication Number Publication Date
US3140261A true US3140261A (en) 1964-07-07

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US (1) US3140261A (en(2012))
BE (1) BE610211A (en(2012))
CH (1) CH417829A (en(2012))
ES (1) ES271949A1 (en(2012))
FR (1) FR1310101A (en(2012))
GB (1) GB949059A (en(2012))
NL (1) NL271294A (en(2012))

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3501409A (en) * 1964-07-22 1970-03-17 Continental Oil Co Detergent-hydrotrope composition
US4487710A (en) * 1982-03-01 1984-12-11 The Procter & Gamble Company Granular detergents containing anionic surfactant and ethoxylated surfactant solubility aid

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5110860B2 (en(2012)) * 1972-08-29 1976-04-07
GB1562801A (en) * 1976-01-02 1980-03-19 Procter & Gamble Liquid detergent composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2855367A (en) * 1954-09-07 1958-10-07 Colgate Palmolive Co Detergent composition
US2932617A (en) * 1956-02-29 1960-04-12 Lever Brothers Ltd Detergent composition containing 2-alkyl-4, 4-bis (hydroxymethyl) oxazolines
US2954348A (en) * 1956-05-28 1960-09-27 Procter & Gamble Detergent compositions
US2978416A (en) * 1955-07-14 1961-04-04 Allied Chem Concentrated aqueous detergent composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2855367A (en) * 1954-09-07 1958-10-07 Colgate Palmolive Co Detergent composition
US2978416A (en) * 1955-07-14 1961-04-04 Allied Chem Concentrated aqueous detergent composition
US2932617A (en) * 1956-02-29 1960-04-12 Lever Brothers Ltd Detergent composition containing 2-alkyl-4, 4-bis (hydroxymethyl) oxazolines
US2954348A (en) * 1956-05-28 1960-09-27 Procter & Gamble Detergent compositions

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3501409A (en) * 1964-07-22 1970-03-17 Continental Oil Co Detergent-hydrotrope composition
US4487710A (en) * 1982-03-01 1984-12-11 The Procter & Gamble Company Granular detergents containing anionic surfactant and ethoxylated surfactant solubility aid

Also Published As

Publication number Publication date
FR1310101A (en(2012)) 1963-03-06
NL271294A (en(2012))
GB949059A (en) 1964-02-12
ES271949A1 (es) 1962-06-01
BE610211A (en(2012))
CH417829A (fr) 1966-07-31

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