US3915881A - Detergent compositions - Google Patents

Detergent compositions Download PDF

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Publication number
US3915881A
US3915881A US428990A US42899073A US3915881A US 3915881 A US3915881 A US 3915881A US 428990 A US428990 A US 428990A US 42899073 A US42899073 A US 42899073A US 3915881 A US3915881 A US 3915881A
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US
United States
Prior art keywords
fatty acid
acid salt
sulphonated
sulphonated fatty
detergent formulation
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
US428990A
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English (en)
Inventor
James Francis Davies
Charles Rowland Gauterin
David Wynn Lewis Griffiths
Christopher Charles Storer
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.)
Lever Brothers Co
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Lever Brothers Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to GB5974470A priority Critical patent/GB1380390A/en
Priority to CH1809271A priority patent/CH576518A5/xx
Priority to DE2161726A priority patent/DE2161726B2/de
Priority to AU36832/71A priority patent/AU464680B2/en
Priority to NL7117087A priority patent/NL7117087A/xx
Priority to FR7145147A priority patent/FR2118670A5/fr
Priority to AT1075771A priority patent/AT340553B/de
Priority to CA130,258A priority patent/CA941261A/en
Application filed by Lever Brothers Co filed Critical Lever Brothers Co
Priority to US428990A priority patent/US3915881A/en
Application granted granted Critical
Publication of US3915881A publication Critical patent/US3915881A/en
Anticipated expiration legal-status Critical
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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
    • 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
    • C11D10/042—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on anionic surface-active 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • 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
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • ABSTRACT The invention describes the use of salts of sulphonated fatty acids as detergency builders.
  • the use of C to C acids is required and a formulation containing 10 to 75% of a builder component including at least one sulphonated fatty acid salt and 5 to 50% of a detergent active is proposed.
  • Preferred actives which demonstrate increased detergency at specific ratios, are alkylaryl sulphonates, nonionic materials and alkane sulphonates.
  • This invention relates to detergent solid and liquid formulations. (The formulations of the invention are particularly intended for the purpose of fabric washing.)
  • Detergent formulations contain an active ingredient and a builder material together with other organic and inorganic substances having specific functions in the wash liquor.
  • the builder material allows the detergent active to perform its cleaning function efficiently.
  • Phosphate materials for example sodium tripolyphosphate, have been used for many years as builder materials; however, recently concern has been expressed regarding the contribution of phosphate to the eutrophi cation of inland waters.
  • the present invention describes formulations containing a reduced or nil level of phosphate which have good detergent properties and can demonstrate softening of fabric during washing.
  • the invention provides a detergent formulation comprising from to 75% by weight of a builder component consisting of water-soluble salt or salts of an alpha-sulphonated saturated fatty acid or mixture thereof containing from 14 to 20 carbon atoms alone or in admixture with other detergency building materials, from 5 to 50% by weight of a detergent active material, from 0.2 to 20% (preferably 0.2% to 15%) by weight of alkali-metal salts of long-chain fatty acids, optionally 5 to 12% by weight of sodium silicate; the remainder being other known components of detergent formulations.
  • a builder component consisting of water-soluble salt or salts of an alpha-sulphonated saturated fatty acid or mixture thereof containing from 14 to 20 carbon atoms alone or in admixture with other detergency building materials, from 5 to 50% by weight of a detergent active material, from 0.2 to 20% (preferably 0.2% to 15%) by weight of alkali-metal salts of long-chain fatty acids, optionally 5 to 12% by weight of sodium
  • the preferred ranges within the broad definition of the invention are from to 50% by weight of the sulphonated fatty acid salts, from 15 to 35% by weight of the detergent active material and from 5 to 15% of alkali-metal salts of long-chain fatty acids.
  • the invention proposes the use of the monoor disalts (either single or mixed, for example sodium/potassium). At the pH value of the wash liquors formed by the compositions of the invention the hydrogen ion of a monosalt would also be ionised to form the doubly charged anion.
  • the sulphonated fatty acid salt will be used alone or as a mixture with one or more of the known detergency builders, for example so-called precipitant builders which form insoluble calcium salts, for example sodium orthophosphate, and sodium alkyl and alkenyl succinates and malonates, and also sequestrant builders which can be either organic or inorganic, for example sodium hydrofuran tetracarboxylate, sodium pyrophosphate, sodium nitrilotriacetate, sodium ethylene diamine tetraacetate, sodium citrate, sodium tartrate, sodium malate, trisodium carboxymethyloxysuccinate, sodium oxydiacetate, sodium oxydisuccinate, and also polyelectrolyte builders such as sodium polyacrylate and copolyethylene maleate.
  • precipitant builders which form insoluble calcium salts
  • sodium orthophosphate sodium orthophosphate
  • sequestrant builders which can be either organic or inorganic, for
  • Both the sodium and potassium salts of the sulphonated fatty acid can be utilized although as will be appreciated from the further description, the sodium salt is preferred.
  • the ammonium, alkyl substituted ammonium and amine salts for example triethanolamine (of use in liquid formulations) can be used.
  • the formulations will contain other known detergent formulation ingredients selected from alkaline materials, e.g., silicate, sulphates, germicides, active oxygen carriers, e.g., perborates, persulphates,
  • the ingredient ranges quoted are broad because the invention contemplates that a formulation of this general formula can be used at certain product concentrations depending on the country of use.
  • detergent powders will usually be used at an in-use product concentration of 0.075 to 0.20% weight to volume
  • European type markets a product in-use concentration of 0.3% to 1% weight to volume is more usual.
  • concentration of sulphonated fatty acid salt will preferably be chosen in the higher part of the quoted range, i.e., 3575%, and for the European type markets preferably in the lower range, i.e., l050%.
  • the surfactant concentration in the powder will preferably be l050% and in the European type powders the surfactant concentration will preferably be 525%.
  • the use of a lower product concentration in the USA requires that the formulation itself has a higher concentration of active and builder material. It is advisable to use the products of the invention at a pH in the wash liquor of above 9.5.
  • anionic active used examples include alcohol sul phates (C and sulphonates, ether sulphates, olefin sulphonates, alkyl aryl sulphates, alkane sulphonates and cationic materials, for example quaternary nitrogen actives.
  • Other anionic actives known for use in detergent formulations can be used.
  • An example of the nonionic active used is the ethoxylated alcohol class; the alcohol preferably having a chain length of C and an average ethoxylation of from 5 to 30, preferably 15 to 25.
  • Other nonionics which will be usable are alkyl-phenols.
  • actives are alkylbenzene sulphonates, nonionic materials, in particular ethoxylated alcohols, and alkane sulphonates.
  • the preferred ratios of these actives to the sulphonated fatty acid salt builder are:
  • Alkylbenzene sulphonate 2 more preferably to 5 Z more preferably 0 1:1
  • Nonionic active 5 l l Alkane sulphonate l l The actives olefin sulphonate, Dobanol 45 5 EO sulphonate and Tergitol l5-S-7 were shown to be comparable with an alkylbenzene sulphonate/sodium tripolyphosphate formulation.
  • the physical form of the solid formulations of this invention may be, for example, flakes, tablets, powders (e.g., blown or spray dried), granules and extruded forms.
  • the preferred range of sulphonated fully hardened fatty acid salt is from 10% to 40%.
  • the alkyl radical must be at least C and preferably C to give good building properties. This is not to say that some amount of C or lower cannot be tolerated, but such materials add little or nothing to the building efficiency.
  • natural fatty acids are mixtures of chain lengths it may be necessary to include some of these non-efficient materials in a formulation or undertake separation of the desired chain lengths.
  • the chain length of the sulphonated fatty acid salt will be kept as low as possible because increase in chain length increases the molecular weight and hence reduces the proportion of the molecule available for building properties. Further, the solubility of the salts falls with increase in molecular weight and it is believed the sodium salt would be of little value above a chain length of C
  • the potassium salt is more soluble. To use the potassium salt may require the other alkali-metal salts in the formulation to be substantially in the potassium form.
  • the ammonium salt may also be used and the triethanolamine salt is of particular applicability to liquid formulations.
  • Alpha-sulphonated fatty acid salt 15 to 65% Alkyl benzene sulphonate 18% Alkaline silicate 10% Sodium sulphate approximately 12% Results of specific formulations (Examples 1 to 6) are given in Table l.
  • alpha-sulphonated fatty acid salts have detergent active properties but appreciation of their properties as builder materials has provided the basis for the present invention.
  • Formulations were prepared using the proportions given in the following Table (by weight). It was found that the amount of lather obtained generally increased with the amount of sulphonated fatty acid salt present.
  • the soap (Pristerine 63 sold by Price Brothers of Bromborough, England) had a chain length distribution of C ,-2%; C -3 1%; C (saturated)-65% and C ,,(unsaturated)-2%. Soaps are alkali-metal salts of long-chain (C -C fatty acids.
  • the sulphonated acids were prepared by reacting the acid with sulphur trioxide.
  • the detergencies were measured using dacron/cotton test cloth soiled with artificial sebum and vacuum cleaner dust in 18H water (Ca:Mg being 2:1) with the aid of a Terg-O-Tometer (1H is 0.0001 M calcium).
  • the wash temperature was 50 or 60C for 10 minutes followed by 1 minute rinse at 25C.
  • the accompanying FIGURE has a graph which plots detergency (Y) against several mixtures of actives (A) and sodium alpha-sulphonated fully hardened tallow fatty acid (B).
  • Rc reflectance of clean material
  • Rs reflectance of soiled material
  • Blown powders were also tested, both with and with out enzymes, and containing an alkyl benzene sulphonate (Oronite 1060) as the surfactant, these blown powders were found to be satisfactory.
  • Redeposition was also studied using various fabrics with Standards B and C quoted previously. The redeposition was measured as the loss of reflectance after 25 wash cycles (see Table III) using an in-wash product 6
  • the preferred ranges for the ratios of active to builder are from 1:6 to 6:1 and most preferred from 2:5 to 5:2.
  • Curve I in the FIGURE demonstrates the increase in concentration of 0.15%.
  • the product according to the 5 detergency achieved by the addition of the sulphonated invention (D) contained 50% sodium fatty acid sulphofatty acid salt to the linear alkyl benzene sulphonate. nate and 20% alkylbenzene sulphonate as active.
  • Nonionic active 5 to 30% sulphonated fatty acid salt 40 to 65%
  • Example VII A S ofd ter em wd
  • the most preferred ranges are nonionic active 10 to Linz r ilkyl iof betlzeneiiiigiigna'tl (H07, 20% together with 50 to 60% of the sulphonated fatty Sodium alpha-sulphonated saturated fatty acid salt. It w1ll be apprec1ated that 1n a commercial ii g f gg z g 35%) 45 formulation the total of active and builder will probably Sodium sulphate, water 20% not equal 70% of the total composmon.
  • the preferred ranges for the ratios of active to builder are from 1:13 to 3:4, the most preferred being from 1:6 to 2:5. Curve were prepared, the total of active sulphonated fatty I1 demonstrates the increase in detergency obtained by acid salt being always 70%.
  • adding a salt of an a-sulphonated fatty acid to a non- Detergencies were determined using a Terg-O-Tomeionic active. ter at 90 rpm.
  • the wash liquor was made up at 0.15% product concentration in 18 hard water (CazMg EXAMPLE IX 2:1
  • the wash was at 50C for 10 minutes followed by Example VII was repeated using a secondary alkane 1 minute rinse at 35C.
  • test cloth was dacron/cotsulphonate (C to C chain length) as the active.
  • the ton with vacuum cleaner dust as soil. product concentration was 0.1%.
  • Dot/dash curve 111 in The detergencies, measured as percentages are the FIGURE shows the detergencies achieved. Expressshown in continuous curve I in FIG. I.
  • preferred ranges as percentages of the total we that preferred ranges are: have Detergent active 10 to 60% Alkane sulphonate active 5 to 50% sulphonated fatty acid salt 60 to 10% sulphonated fatty acid salt 20 to The most preferred ranges are from 20 to 50% for the The most preferred ranges are alkane sulphonate ac- 65 tive 10 to 35% together with sulphonated fatty acid salt active together with 50 to 20% of the sulphonated fatty acid salt. It will be appreciated that in commercial formulations the total sum of active builder will normally not equal of the total.
  • ratios of active to builder the preferred ranges are from 1:13 to 5:2, the most preferred ratios being from 1:6 to 1:1. It will be noted that 7 addition of a salt of an alpha-sulphonated fatty acid increases the detergency of the active.
  • a detergent formulation comprising i. from 10 to by weight of a builder component consisting of water soluble salt or salts of an alphasulphonated saturated fatty acid or mixture thereof containing from 14 to 20 carbon atoms alone or in a mixture with other detergency building materials, from 5 to 50% by weight of a detergent active material selected from the group consisting of an alkyl benzene sulphonate having from 8 to 20 carbon atoms and present in a ratio of from 1:6 to 6:1 relative to the sulphonated fatty acid salt; an ethoxylated alcohol wherein the alcohol has a chain length of C C and an average ethoxylation of from 5 to 30 present in a ratio of from 1:13 to 3:4 relative to the sulphonated fatty acid salt; and an alkane sulphonate which is present in a ratio of from 1:13 to 5:2 relative to the sulphonated fatty acid salt,
  • a detergent formulation according to claim 1 wherein the alkyl benzene sulphonate to sulphonated fatty acid salt ratio is from 2:5 to 5:2.
  • a detergent formulation according to claim 1 including 5 to 12% of a sodium silicate.

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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)
US428990A 1970-12-16 1973-12-27 Detergent compositions Expired - Lifetime US3915881A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB5974470A GB1380390A (en) 1970-12-16 1970-12-16 Detergent compositions
CH1809271A CH576518A5 (enrdf_load_stackoverflow) 1970-12-16 1971-12-10
DE2161726A DE2161726B2 (de) 1970-12-16 1971-12-13 Waschmittel mit verringertem oder ohne Gehalt an Phosphaten
NL7117087A NL7117087A (enrdf_load_stackoverflow) 1970-12-16 1971-12-14
AU36832/71A AU464680B2 (en) 1970-12-16 1971-12-14 Detergent compositions
FR7145147A FR2118670A5 (enrdf_load_stackoverflow) 1970-12-16 1971-12-15
AT1075771A AT340553B (de) 1970-12-16 1971-12-15 Textilwaschmittel
CA130,258A CA941261A (en) 1970-12-16 1971-12-16 Detergent compositions
US428990A US3915881A (en) 1970-12-16 1973-12-27 Detergent compositions

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB5974470A GB1380390A (en) 1970-12-16 1970-12-16 Detergent compositions
US20785671A 1971-12-14 1971-12-14
US428990A US3915881A (en) 1970-12-16 1973-12-27 Detergent compositions

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US3915881A true US3915881A (en) 1975-10-28

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US428990A Expired - Lifetime US3915881A (en) 1970-12-16 1973-12-27 Detergent compositions

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US (1) US3915881A (enrdf_load_stackoverflow)
AT (1) AT340553B (enrdf_load_stackoverflow)
AU (1) AU464680B2 (enrdf_load_stackoverflow)
CA (1) CA941261A (enrdf_load_stackoverflow)
CH (1) CH576518A5 (enrdf_load_stackoverflow)
DE (1) DE2161726B2 (enrdf_load_stackoverflow)
FR (1) FR2118670A5 (enrdf_load_stackoverflow)
GB (1) GB1380390A (enrdf_load_stackoverflow)
NL (1) NL7117087A (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025147A1 (de) * 1979-08-25 1981-03-18 Van Baerle & Co. KG Flüssiges, phosphatarmes und umweltfreundliches Waschmittel
US4438025A (en) 1981-12-30 1984-03-20 Lion Corporation Detergent compositions
US4549984A (en) * 1983-06-30 1985-10-29 Lion Corporation Liquid detergent composition
US20060019859A1 (en) * 2004-07-23 2006-01-26 Melani Duran Powder dilutable multi-surface cleaner
WO2025045870A1 (en) * 2023-08-30 2025-03-06 Unilever Ip Holdings B.V. Solid laundry composition

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EP0008141A1 (en) * 1978-08-07 1980-02-20 THE PROCTER & GAMBLE COMPANY Detergent composition containing mixture of anionic sulfate and sulfonate surfactants
EP0241073B2 (en) * 1986-03-31 1995-03-08 The Procter & Gamble Company Liquid detergents containing anionic surfactant, succinate builder and fatty acid
DE3827778A1 (de) 1988-08-16 1990-02-22 Henkel Kgaa Pastenfoermiges wasch- und reinigungsmittel und verfahren zur herstellung
DE4107731A1 (de) * 1991-03-11 1992-09-17 Henkel Kgaa Organische builder mit tensideigenschaften
US7666828B2 (en) 2008-01-22 2010-02-23 Stepan Company Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them
US7879790B2 (en) 2008-01-22 2011-02-01 Stepan Company Mixed salts of sulfonated estolides and other derivatives of fatty acids, and methods of making them
US7998920B2 (en) 2008-01-22 2011-08-16 Stepan Company Sulfonated estolide compositions containing magnesium sulfate and processes employing them
US8119588B2 (en) 2009-01-21 2012-02-21 Stepan Company Hard surface cleaner compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
US7884064B2 (en) 2009-01-21 2011-02-08 Stepan Company Light duty liquid detergent compositions of sulfonated estolides and other derivatives of fatty acids
US8058223B2 (en) 2009-01-21 2011-11-15 Stepan Company Automatic or machine dishwashing compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
BRPI0924129B1 (pt) * 2009-01-21 2019-09-17 Stepan Company Composição agrícola de estolides sulfonados e outros derivados de ácidos graxos
US8124577B2 (en) 2009-01-21 2012-02-28 Stepan Company Personal care compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
EP2456755B1 (en) * 2009-07-21 2015-12-16 Stepan Company Mixed salts of sulfonated estolides and other derivatives of fatty acids, and methods of making them
EP2277860B1 (en) * 2009-07-22 2015-08-19 Stepan Company Compositions comprising sulfonated estolides and alkyl ester sulfonates, methods of making them, and compositions and processes employing them
BR112012008306A2 (pt) 2009-09-11 2020-08-25 Stepan Company composições líquidas de limpeza que contenham estolides sulfonados e sulfonatos éster-alquílicos.

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US2954347A (en) * 1955-10-27 1960-09-27 Procter & Gamble Detergent composition
US3274117A (en) * 1962-05-17 1966-09-20 Henkel & Cie Gmbh Pourable and free-flowing detergent, wetting, and emulsifying compositions
US3345301A (en) * 1963-10-23 1967-10-03 Henkel & Cie Gmbh Pourable and free-flowing detergent, wetting, and emulsifying compositions
US3351559A (en) * 1963-11-13 1967-11-07 Henkel & Cie Gmbh Pourable and free-flowing detergent, wetting, and emulsifying compositions
US3377289A (en) * 1964-01-10 1968-04-09 Henkel & Compagnie G M B H Liquid or paste soap preparations having sulfo fatty acid salts as viscosity reducing agents
US3390096A (en) * 1964-06-27 1968-06-25 Henkel & Cie Gmbh Combinations of wash-active substances in liquid or paste form
US3585144A (en) * 1967-01-19 1971-06-15 Swift & Co Scouring pad
US3632517A (en) * 1970-08-21 1972-01-04 Us Agriculture Synergistic tallow-based detergent compositions

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FR1439826A (fr) * 1962-04-30 1966-05-27 Procter & Gamble Pain de toilette
DE1225798B (de) * 1963-09-02 1966-09-29 Henkel & Cie Gmbh Schuett- und rieselfaehige, insbesondere pulverfoermige Wasch-, Netz- und Emulgiermittel

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2954347A (en) * 1955-10-27 1960-09-27 Procter & Gamble Detergent composition
US3274117A (en) * 1962-05-17 1966-09-20 Henkel & Cie Gmbh Pourable and free-flowing detergent, wetting, and emulsifying compositions
US3345301A (en) * 1963-10-23 1967-10-03 Henkel & Cie Gmbh Pourable and free-flowing detergent, wetting, and emulsifying compositions
US3351559A (en) * 1963-11-13 1967-11-07 Henkel & Cie Gmbh Pourable and free-flowing detergent, wetting, and emulsifying compositions
US3377289A (en) * 1964-01-10 1968-04-09 Henkel & Compagnie G M B H Liquid or paste soap preparations having sulfo fatty acid salts as viscosity reducing agents
US3390096A (en) * 1964-06-27 1968-06-25 Henkel & Cie Gmbh Combinations of wash-active substances in liquid or paste form
US3585144A (en) * 1967-01-19 1971-06-15 Swift & Co Scouring pad
US3632517A (en) * 1970-08-21 1972-01-04 Us Agriculture Synergistic tallow-based detergent compositions

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025147A1 (de) * 1979-08-25 1981-03-18 Van Baerle & Co. KG Flüssiges, phosphatarmes und umweltfreundliches Waschmittel
US4438025A (en) 1981-12-30 1984-03-20 Lion Corporation Detergent compositions
US4549984A (en) * 1983-06-30 1985-10-29 Lion Corporation Liquid detergent composition
US20060019859A1 (en) * 2004-07-23 2006-01-26 Melani Duran Powder dilutable multi-surface cleaner
WO2025045870A1 (en) * 2023-08-30 2025-03-06 Unilever Ip Holdings B.V. Solid laundry composition

Also Published As

Publication number Publication date
DE2161726A1 (de) 1972-07-06
GB1380390A (en) 1975-01-15
CA941261A (en) 1974-02-05
AU3683271A (en) 1973-06-21
NL7117087A (enrdf_load_stackoverflow) 1972-06-20
AT340553B (de) 1977-12-27
CH576518A5 (enrdf_load_stackoverflow) 1976-06-15
DE2161726B2 (de) 1981-02-05
AU464680B2 (en) 1975-09-04
ATA1075771A (de) 1977-04-15
FR2118670A5 (enrdf_load_stackoverflow) 1972-07-28

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