US3415753A - Liquid and paste detergent concentrates - Google Patents

Liquid and paste detergent concentrates Download PDF

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Publication number
US3415753A
US3415753A US465164A US46516465A US3415753A US 3415753 A US3415753 A US 3415753A US 465164 A US465164 A US 465164A US 46516465 A US46516465 A US 46516465A US 3415753 A US3415753 A US 3415753A
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United States
Prior art keywords
olefin
viscosity
paste
liquid
percent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US465164A
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English (en)
Inventor
Stein Werner
Umbach Wilfried
Baumann Horst
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Filing date
Publication date
Priority to DEH53097A priority Critical patent/DE1254798B/de
Priority to NL6506793A priority patent/NL6506793A/xx
Priority to FR21060A priority patent/FR1451320A/fr
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to US465164A priority patent/US3415753A/en
Priority to GB26941/65A priority patent/GB1055709A/en
Application granted granted Critical
Publication of US3415753A publication Critical patent/US3415753A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143Sulfonic acid esters
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/37Mixtures of compounds all of which are anionic

Definitions

  • the process lies in the finding that by incorporating into the paste and/or liquid detergent concentrate a surface active olefin disulfonate the viscosity of the concentrate is significantly reduced and in addition the wetting and cleansing activity of the wash active materials present in the detergent are enhanced.
  • the invention also includes the resultant concentrates characterized by reduced viscosity.
  • This invention relates to a method and composition for the reduction of the viscosity of liquid or paste detergent concentrates by means of an olefin disulfonate.
  • Liquid or paste detergent concentrates are not only used in compounded form as liquid washing, cleaning or rinsing agent, but also are regularly used as intermediates in the industrial production of corresponding washing powders. Such concentrates frequently have a high viscosity which makes their industrial utilization difficult, especially their conveyance or admixing with other components, as well as handling them in daily use upon dosaging or diluting with water. These difliculties encountered with high viscosity are particularly noticeable in detergent concentrates containing surface-active monoolefin sulfonates.
  • Surface-active monoolefin sulfonates include sulfonation products obtained from the reaction of aliphatic monoolefins of a chain length of C to C with strong sulfonating agents such as oleum, chlorosulfonic acid or sulfur trioxide followed by hydrolysis, the manufacture of which is described, for instance, in US. Patents 2,061,617 to 2,061,620 and 2,094,- 451.
  • anionic hydrotropic substances such as the sulfonates of benzene, toluene or xylene.
  • anionic hydrotropic substances such as the sulfonates of benzene, toluene or xylene.
  • composition of the present invention comprises liquid or paste detergent concentrates containing monoolefin a-sulfonates of a chain length of C to C and preferably of C to C and at least one other anionic or non-ionic wash-active material characterized by a total content of surface-active, wash-active material of 10 to 60 percent by weight and an amount of 0.5 to 25 percent by weight, preferably 1 to 15 percent by weight of olefin disulfonate referred, in each case, to the Weight of solution or paste.
  • the monoolefin disulfonates which serve to reduce the viscosity of the aqueous detergent concentrate are characterized by a chain length of C to C and preferably C to C and by two sulfonate groups in the molecule, and are obtained by reacting monosulfonates of monoolefins with sulf-ur trioxide.
  • the preparation of the monoolefin sulfonates of this invention is effected through sulfonation of monoolefins with S0 or chlorosulfonic acid and subsequent saponification, which is generally described in US. Patents 2,061,617 to 2,061,620 and 2,094,451.
  • S0 sulfonation of monoolefins with S0 or chlorosulfonic acid and subsequent saponification
  • the total concentration of organic wash-active material in the liquid detergent concentrates and pastes of the invention can lie within the range of 10 to 60, and preferably 10 to 50 percent by weight, referred to the weight of the entire solution or paste.
  • the quantitative ratio by weight of olefin sulfonate to olefin disulfonate is advisedly between 20:1 and 1:4, and preferably between 10:1 and 1:2. In the preferred range, the viscosity-reducing action of the olefin disulfonates is particularly effective.
  • the total content of sulfonated and disulfonated olefins in the concentrates should be 5 to 40 percent by weight.
  • the concentrates also contain at least one other anionic or non-ionic surface-active wash-active material such as alkali soaps of fatty acids as well as wash-active materials of the sulfate or sulfonate type, such as primary or secondary alkyl sulfonates, sulfated alkyl polyglycolethers, sulfate alkyl phenol polyglycol ethers, alkyl benzene sulfonate, oz sulfo fatty acid esters, and the like.
  • wash-active material such as alkali soaps of fatty acids
  • wash-active materials of the sulfate or sulfonate type such as primary or secondary alkyl sulfonates, sulfated alkyl polyglycolethers, sulfate alkyl phenol polyglycol ethers, alkyl benzene sulfonate, oz sulfo fatty acid esters, and the like
  • Suitable non-ionic wash-active materials are alkyl polyglycol ethers, alkyl phenol polyglycol ethers and fatty acid condensation products comprising esters and amides.
  • the amount of such wash-active materials in the concentrates is at least 5 percent by weight and preferably 10 to 45 percent by weight, referred to the weight of the solution or paste.
  • the olefin monosulfonates, olefin disulfonates and the other anionic wash-active raw materials contained in the concentrates can be used as sodium, potassium or ammonium salts or else as salts of organic bases, such as mono-, dior triethanolamine.
  • the said salts or cations can also be present in mixture, which is frequently ad vantageous for the preparation of highly concentrated clear solutions.
  • the detergent concentrates in accordance with the invention are particularly suitable for the incorporation of components and addition substances customarily used in washing and cleaning agents.
  • these include the wash-alkalis such as carbonates and pyro-, polyand metaphosphates, as well as the silicates of alkalis.
  • the known organic chelate formers e.g., ethylenediamine-tetracetic acid and its equivalents, can also be incorporated in the concentrates of the invention.
  • organic high-molecular colloid substances particularly water-soluble derivatives of cellulose or of starch as well as water-soluble salts of polyacrylic acid or polymethacrylic acid can be added to them.
  • concentrates are to be used directly as detergent or cleaning agents, they can also contain known solvents, such as monohydric or polyhydric alcohols, polyglycols or polyglycerins.
  • solvents such as monohydric or polyhydric alcohols, polyglycols or polyglycerins.
  • coloring substances and perfumes there enter into consideration coloring substances and perfumes, optical brighteners, skin-protecting substances and stabilizers.
  • the viscosity of the 40-percent alkyl benzene sulfonate solution is 4650 centipoises and that of a 40-percent olefin sulfonate solution is 1100 centipoises.
  • a solution containing percent alkyl benzene sulfonate and 10 percent olefin sulfonate would theoretically have to have, by application of the mixture rule, a viscosity of about 3700 centipoises, as compared to an actually found value of 9000 centipoises.
  • the monoolefin sulfonates and monoolefin disulfonates qggs percent percent used in the following Examples I to IX contain 14 to p 18 carbon atoms in the molecule (average chain length I C and are in the form of sodium Salts.
  • Th lky II 30 ""16""131:112133113: 9:000 sulfate of Example VI comprises the sodium salt of a 3g 2 g kggg sulfated fatty alcohol of a chain length of C to C1 15 15 670 (average chain length C
  • the Texapon N (regism Z 23 tered trademark) of Examples IV and V is the sodium salt of a coconut fatty alcohol of an average chain length of 12 to m, which is reacted with 2 mols of ethylene Ex. No. ii r t suiiii ri aiie, disgaffiriiirte, Viscosity cp. oxide and thereupon sulfated.
  • the alkyl polyglycol ether percent percent of Examples VII and IX is obtained by addition 0f 3O 2300 10 mols of ethylene oxide to a fatty alcohol of a chain IV 20 10 '260 length of C to C and an iodine number of 50.
  • the 28 2 2 2g sulfo-ester of Example VIII is the sodium salt of an V 10 20 5s a-sulfo-fatty acid methyl ester from hydrogenated palm 2 125 $12 nut fatty acid.
  • the soap of Example IX is a sodium soap of saturated fatty aclds of a cham length of C Olefin olefin to C22 (average chain length C18). Ex. No. sulfate, sulfonate, disulfonate, Viscosity, op.
  • the viscosity of the aqueous solutions is measured in Percent Parcelt 119mm each case at a temperature of 20 C. after standing for 30 three weeks, by means of a Hoppler drop-ball viscosim- VI gg eter (DIN 53,015) in Examples I, III to V and VII t0 15 5.5 9.5 6.7 XI, and with an Epprecht rotary viscosimeter [I. R. van ,solid Wazer et al., Viscosity and Flow Measurement, Inter- Mk 1 science Publishers, (New York 1963) pp. 129-135] in o1 Olefin Olefind- Examples II and VI. The percentages set forth 1n the Ex. N0 l slflogatg, sulfonatc Viscosity, cp.
  • 1 6D GICGH tables are percentages by weight. percent P P
  • the alkyl benzene sulfonate/olefin sulfonate/olefin d1- sulfonate system is examined in different mixture ratios, VII 32 228 the concentration of the total solution being maintained 3 4 106 constant in Example I, the concentration of the alkyl 5 31 Sulfo- Olefin Olefin di- Ex. No. ester, NazS04, sulionate, sulfonate, Viscosity, cp.
  • a paste or liquid detergent concentrate consisting essentially of an wmonoolefin monosulfonate containing 8 to 24 carbon atoms and an a-olefin disulfonate containing 8 to 24 carbon atoms as viscosity reducing agent, said a-olefin disulfonate being present in an amount of from 0.5 to 25% by weight of said detergent concentrate.
  • a paste or liquid detergent concentrate according to claim 1 additionally containing at least one other wash active material selected from the group consist-ing of organic anionic and nonionic detergents, the total amount of monosulfonate and disulfonate and wash active trnaterials present in said concentrate amounting to 10 to 60% by Weight of said concentrate.
  • a paste or liquid detergent concentrate according to claim 4 wherein said additional wash active material is at least one member selected from the group consisting of alkali soaps of fatty acids, alkyl sulfates, alkyl polyglycol ether sulfates, alkyl benzene sulfonates, asulfo fatty acid esters, alkyl polyglycol ethers and alkyl phenol polyglycol ethers.
  • a paste or liquid detergent concentrate according to claim 4 additionally including at least one further member selected from the group consisting of alkali metal carbonate, organic chelating agent, a water-soluble derivative of cellulose or starch, water-soluble salts of polyacrylic acid or polymethacrylic acid, a solvent, a perfume, and an optical brightener.

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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)
  • Dispersion Chemistry (AREA)
  • Detergent Compositions (AREA)
US465164A 1964-06-26 1965-06-18 Liquid and paste detergent concentrates Expired - Lifetime US3415753A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DEH53097A DE1254798B (de) 1964-06-26 1964-06-26 Fluessige oder pastenfoermige Waschmittelkonzentrate
NL6506793A NL6506793A (xx) 1964-06-26 1965-05-28
FR21060A FR1451320A (fr) 1964-06-26 1965-06-16 Mélange détergent, notamment sous forme de liquides ou de pâtes
US465164A US3415753A (en) 1964-06-26 1965-06-18 Liquid and paste detergent concentrates
GB26941/65A GB1055709A (en) 1964-06-26 1965-06-25 Washing agents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEH53097A DE1254798B (de) 1964-06-26 1964-06-26 Fluessige oder pastenfoermige Waschmittelkonzentrate
US465164A US3415753A (en) 1964-06-26 1965-06-18 Liquid and paste detergent concentrates

Publications (1)

Publication Number Publication Date
US3415753A true US3415753A (en) 1968-12-10

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US465164A Expired - Lifetime US3415753A (en) 1964-06-26 1965-06-18 Liquid and paste detergent concentrates

Country Status (4)

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US (1) US3415753A (xx)
DE (1) DE1254798B (xx)
GB (1) GB1055709A (xx)
NL (1) NL6506793A (xx)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3755203A (en) * 1970-12-17 1973-08-28 Jefferson Chem Co Inc Detergent slurry compositions
US3852221A (en) * 1971-08-19 1974-12-03 Jefferson Chem Co Inc Liquid olefin sulfonate detergent
US4003857A (en) * 1973-12-17 1977-01-18 Ethyl Corporation Concentrated aqueous olefins sulfonates containing carboxylic acid salt anti-gelling agents
US4006111A (en) * 1972-07-12 1977-02-01 Lever Brothers Company Production of alkane: olefin sulfonate mixtures by sequential sulfonation and sulfitation
US4139498A (en) * 1975-12-26 1979-02-13 The Lion Fat & Oil Co., Ltd. Process of manufacturing high-concentration olefin sulfonate solution
US4239641A (en) * 1978-08-03 1980-12-16 Basf Aktiengesellschaft Use of polyhydric alcohols, carboxylic acids, hydroxy-carboxylic acids and/or their esters with polyhydric alcohols as viscosity regulators
US4279786A (en) * 1978-12-26 1981-07-21 The Lion Fat & Oil Co., Ltd. Homogeneous aqueous alpha-olefin sulfonate composition
US4532076A (en) * 1982-02-11 1985-07-30 Henkel Kommanditgesellschaft Auf Aktien Aqueous anionic surfactant concentrates containing viscosity reducing agents
US4537253A (en) * 1981-10-09 1985-08-27 Lion Corporation Micellar slug for oil recovery
US4555351A (en) * 1982-01-28 1985-11-26 Lion Corporation Micellar slug for oil recovery
US4556108A (en) * 1982-01-28 1985-12-03 Lion Corporation Micellar slug for oil recovery
US4597879A (en) * 1982-01-28 1986-07-01 Lion Corporation Micellar slug for oil recovery
EP0243927A2 (en) * 1986-05-01 1987-11-04 Kao Corporation Liquid detergent composition
US4804491A (en) * 1986-11-03 1989-02-14 The Clorox Company Aqueous based acidic hard surface cleaner
US4820448A (en) * 1986-09-08 1989-04-11 Henkel Kommanditgesellschaft Auf Aktien Surfactant mixtures and their use
US4895669A (en) * 1986-11-03 1990-01-23 The Clorox Company Aqueous based acidic hard surface cleaner
US4911238A (en) * 1988-12-19 1990-03-27 Shell Oil Company Gas flooding with surfactants enriched in olefin disulfonate
US4957646A (en) * 1987-08-26 1990-09-18 Shell Oil Company Steam foam surfactants enriched in alpha olefin disulfonates for enhanced oil recovery
US5069802A (en) * 1988-12-19 1991-12-03 Shell Oil Company Gas flood surfactants enriched in olefin disulfonate
US5110487A (en) * 1989-04-03 1992-05-05 Chevron Corporation Enhanced oil recovery method using surfactant compositions for improved oil mobility
WO1992016606A1 (de) * 1991-03-21 1992-10-01 Henkel Kommanditgesellschaft Auf Aktien Verfahren zur herstellung von hochkonzentrierten fettalkoholsulfat-pasten
US5538669A (en) * 1990-11-09 1996-07-23 Henkel Kommanditgesellschaft Auf Aktien Stabilized surfactant paste

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1546127A (en) * 1976-11-18 1979-05-16 Shell Int Research Detergent compositions
JPS6011595A (ja) * 1983-06-30 1985-01-21 ライオン株式会社 液体洗浄剤組成物
DE4035722A1 (de) * 1990-11-09 1992-05-14 Henkel Kgaa Stabilisierte tensidpaste
FR2714674B1 (fr) * 1994-01-06 1996-03-15 Stepan Europe Agents hydrotropes et compositions les contenant.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3755203A (en) * 1970-12-17 1973-08-28 Jefferson Chem Co Inc Detergent slurry compositions
US3852221A (en) * 1971-08-19 1974-12-03 Jefferson Chem Co Inc Liquid olefin sulfonate detergent
US4006111A (en) * 1972-07-12 1977-02-01 Lever Brothers Company Production of alkane: olefin sulfonate mixtures by sequential sulfonation and sulfitation
US4003857A (en) * 1973-12-17 1977-01-18 Ethyl Corporation Concentrated aqueous olefins sulfonates containing carboxylic acid salt anti-gelling agents
US4139498A (en) * 1975-12-26 1979-02-13 The Lion Fat & Oil Co., Ltd. Process of manufacturing high-concentration olefin sulfonate solution
US4239641A (en) * 1978-08-03 1980-12-16 Basf Aktiengesellschaft Use of polyhydric alcohols, carboxylic acids, hydroxy-carboxylic acids and/or their esters with polyhydric alcohols as viscosity regulators
US4279786A (en) * 1978-12-26 1981-07-21 The Lion Fat & Oil Co., Ltd. Homogeneous aqueous alpha-olefin sulfonate composition
US4537253A (en) * 1981-10-09 1985-08-27 Lion Corporation Micellar slug for oil recovery
US4555351A (en) * 1982-01-28 1985-11-26 Lion Corporation Micellar slug for oil recovery
US4556108A (en) * 1982-01-28 1985-12-03 Lion Corporation Micellar slug for oil recovery
US4597879A (en) * 1982-01-28 1986-07-01 Lion Corporation Micellar slug for oil recovery
US4532076A (en) * 1982-02-11 1985-07-30 Henkel Kommanditgesellschaft Auf Aktien Aqueous anionic surfactant concentrates containing viscosity reducing agents
EP0243927A2 (en) * 1986-05-01 1987-11-04 Kao Corporation Liquid detergent composition
EP0243927A3 (en) * 1986-05-01 1988-08-17 Kao Corporation Liquid detergent composition
US4820448A (en) * 1986-09-08 1989-04-11 Henkel Kommanditgesellschaft Auf Aktien Surfactant mixtures and their use
US4804491A (en) * 1986-11-03 1989-02-14 The Clorox Company Aqueous based acidic hard surface cleaner
US4895669A (en) * 1986-11-03 1990-01-23 The Clorox Company Aqueous based acidic hard surface cleaner
US4957646A (en) * 1987-08-26 1990-09-18 Shell Oil Company Steam foam surfactants enriched in alpha olefin disulfonates for enhanced oil recovery
US4911238A (en) * 1988-12-19 1990-03-27 Shell Oil Company Gas flooding with surfactants enriched in olefin disulfonate
US5069802A (en) * 1988-12-19 1991-12-03 Shell Oil Company Gas flood surfactants enriched in olefin disulfonate
US5110487A (en) * 1989-04-03 1992-05-05 Chevron Corporation Enhanced oil recovery method using surfactant compositions for improved oil mobility
US5538669A (en) * 1990-11-09 1996-07-23 Henkel Kommanditgesellschaft Auf Aktien Stabilized surfactant paste
WO1992016606A1 (de) * 1991-03-21 1992-10-01 Henkel Kommanditgesellschaft Auf Aktien Verfahren zur herstellung von hochkonzentrierten fettalkoholsulfat-pasten
US5446188A (en) * 1991-03-21 1995-08-29 Henkel Kommanditgesellschaft Auf Aktien Process for the production of highly concentrated fatty alcohol sulfate pastes

Also Published As

Publication number Publication date
NL6506793A (xx) 1965-12-27
GB1055709A (en) 1967-01-18
DE1254798B (de) 1967-11-23

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