EP0399581A2 - Compositions tensio-actives - Google Patents

Compositions tensio-actives Download PDF

Info

Publication number
EP0399581A2
EP0399581A2 EP90201047A EP90201047A EP0399581A2 EP 0399581 A2 EP0399581 A2 EP 0399581A2 EP 90201047 A EP90201047 A EP 90201047A EP 90201047 A EP90201047 A EP 90201047A EP 0399581 A2 EP0399581 A2 EP 0399581A2
Authority
EP
European Patent Office
Prior art keywords
weight
per cent
range
alcohol
composition
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.)
Withdrawn
Application number
EP90201047A
Other languages
German (de)
English (en)
Other versions
EP0399581A3 (fr
Inventor
Louis Kravetz
Kirk Herbert Raney
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of EP0399581A2 publication Critical patent/EP0399581A2/fr
Publication of EP0399581A3 publication Critical patent/EP0399581A3/fr
Withdrawn legal-status Critical Current

Links

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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/83Mixtures of non-ionic with anionic compounds
    • 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
    • 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
    • C11D1/29Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols

Definitions

  • This invention relates to liquid and solid surface active compositions of high active matter content comprising a mixture of an alcohol ethoxylate and an alcohol ethoxysulfate.
  • Liquid surfactant compositions are well known in the field of laundry detergents and, whether for domestic or industrial applications, practically all of the available formulations are solutions of one or more surface active materials (surfactants) in water, together with an organic solvent if necessary. Such formulations usually contain only about 10 wt% to 45 wt% active matter.
  • alcohol ethoxy­sulfates are finding increasing use in household laundry powders and liquids as part of mixed active surfactant systems.
  • a drawback to the use of alcohol ethoxysulfates in formulations is their strong gel forming tendencies as they are diluted into formulations having concentrations greater than 30%. Gel formation can be reduced by incorporating approximately 14% ethanol into 60% active matter solutions of alcohol ethoxysulfates. This relatively high active matter solution lowers shipping costs, but the presence of ethanol in alcohol ethoxysulfate solutions prevents their use in spray-dried or dry-blended laundry powders where the flammability and combustibility of ethanol are a significant processing hazard. In addition, excessive water prohibits the formation of a free-­flowing powder when surfactant concentrates are blended with water-soluble detergent powder particles.
  • It is therefore an object of this invention to prepare surface active compositions comprising a blend of alcohol ethoxylates and alcohol ethoxysulfates with less than 15% water and substantially free of any organic solvent.
  • an anionic surfactant, alcohol ethoxysulfate is blended with a nonionic surfactant, alcohol ethoxylate, where each of these surfactant types act as mutual hydrotropes, thereby permitting liquid concentrates containing active matter levels of at least 85%.
  • This invention relates to a surface active composition which is either or liquid or a dry powder, which comprises: a) from 15 per cent by weight to 99 per cent by weight of an alcohol ethoxylate having the formula R-O(CH2CH2O) n -H, wherein R is an alkyl group having from 8 to 18 carbon atoms or an alkylaryl group having an alkyl moiety in the range of from 8 to 12 carbon atoms, and n represents the average number of oxyethylene groups per mole­cule and is a number in the range of from 1 to 12, b) from 1 per cent by weight to 80 per cent by weight of a salt of an alcohol ethoxysulfate having the formula R′ -O-(CH2CH2O) x -SO3M, wherein R′ is an alkyl group having from 8 to 18 carbon atoms or an alkylaryl group having an aikyl moiety in the range of from 8 to 11 carbon atoms, M is a cation selected from an
  • This invention also relates to powder detergent compositions prepared utilizing these surfactant compositions and processes for preparing them.
  • composition is also substantially free of organic solvents, particularly low molecular weight organic solvents and more particularly, lower alcohols having from 1 to 5 carbon atoms, particularly ethanol and methanol.
  • organic solvents particularly low molecular weight organic solvents and more particularly, lower alcohols having from 1 to 5 carbon atoms, particularly ethanol and methanol.
  • liquid shall mean a pourable material which is neither a solid nor a gel.
  • substantially free of an organic solvent shall mean that the amount of organic solvent present, if any, is less than the amount which would substantially alter the properties of the composition.
  • the composition typically contains less than 3 per cent by weight of organic solvent, per total weight of the composition.
  • R-O- (CH2-CH2O) n -H (I) wherein R is a straight-chain or branched-chain alkyl group having in the range of from 8 to 18 carbon atoms, preferably from 12 to 18 carbon atoms, or an alkylaryl group having an alkyl moiety having from 8 to 12 carbon atoms, and n represents the average number of oxyethylene groups per molecule and is in the range of from 1 to 12, preferably from 2 to 9 and more preferably from 2 to 5.
  • the alkyl group can have a carbon chain which is straight or branched, and the ethoxylate component can be a combination of straight-chain and branched molecules.
  • the ethoxylate component can be a combination of straight-chain and branched molecules.
  • about 85 per cent of the R groups in the instant composition are straight-chain.
  • R can be substituted with any substituent which is inert such as, for example, halo groups.
  • Ethoxylates within this class are conventionally prepared by the sequential addition of ethylene oxide to the corresponding alcohol (ROH) in the presence of a catalyst.
  • the alcohol ethoxylate component of this invention is preferably derived by ethoxylation of primary or secondary, straight-chain or branched alcohols.
  • the most common ethoxylates in this class and the ones which are particularly useful in this invention are the primary alcohol ethoxylates, i.e., compounds of formula I in which R is an alkyl group and the -O-(CH2-CH2O) n -H ether substituent is bound to a primary carbon of the alkyl group.
  • Alcohols which are suitable for ethoxylation to form the alcohol ethoxylate component of this invention include coconut fatty alcohols, tallow fatty alcohols, and the commercially available synthetic long-chain fatty alcohol blends, e.g., the C12 to C15 alcohol blends available as NEODOL 25 Alcohol (a registered trademark of product manufactured and sold by Shell Chemical Company), the C12 to C14 alcohol blends available as Tergitol 24L (a registered trademark of product manufactured and sold by Union Carbide Corporation), and the C12 to C13 alcohol blends available, for example, as NEODOL 23 Alcohol (Shell).
  • NEODOL 25 Alcohol a registered trademark of product manufactured and sold by Shell Chemical Company
  • Tergitol 24L a registered trademark of product manufactured and sold by Union Carbide Corporation
  • C12 to C13 alcohol blends available, for example, as NEODOL 23 Alcohol (Shell).
  • Suitable alcohol ethoxylates can be prepared by adding to the alcohol or mixture of alcohols to be ethoxylated a calculated amount, e.g., from 0.1 per cent by weight to 0.6 per cent by weight, preferably from 0.1 per cent by weight to 0.4 per cent by weight, based on total alcohol, of a strong base, typically an alkali metal or alkaline earth metal hydroxide such as sodium hydroxide or potassium hydroxide, which serves as a catalyst for ethoxylation.
  • a strong base typically an alkali metal or alkaline earth metal hydroxide such as sodium hydroxide or potassium hydroxide, which serves as a catalyst for ethoxylation.
  • the resulting mixture is dried, as by vapor phase removal of any water present, and an amount of ethylene oxide calculated to provide from 1 mole to 12 moles of ethylene oxide per mole of alcohol is then introduced and the resulting mixture is allowed to react until the ethylene oxide is consumed, the course of the reaction being followed by the decrease in reaction pressure.
  • the ethoxylation is typically conducted at elevated tempera­tures and pressures. Suitable reaction temperatures range from 120 °C to 220 °C with the range of from 140 °C to 160 °C being pre­ferred.
  • a suitable reaction pressure is achieved by introducing to the reaction vessel the required amount of ethylene oxide which has a high vapor pressure at the desired reaction temperature.
  • the partial pressure of the ethylene oxide reactant is preferably limited, for instance, to less than 4 bar, and/or the reactant is preferably diluted with an inert gas such as nitrogen, for instance, to a vapor phase concentration of 50 per cent or less.
  • the reaction can, however, be safely accomplished at greater ethylene oxide concentration, greater total pressure and greater partial pressure of ethylene oxide if suitable precautions, known to the art, are taken to manage the risks of explosion.
  • the pressure serves as a measure of the degree of the reaction and the reaction is considered to be substantially complete when the pressure no longer decreases with time.
  • the ethoxylation procedure serves to introduce a desired average number of ethylene oxide units per mole of alcohol ethoxylate.
  • treatment of an alcohol mixture with 3 moles of ethylene oxide per mole of alcohol serves to effect the ethoxylation of each alcohol molecule with an average of 3 ethylene oxide moieties per mole alcohol moiety, although a substantial proportion of alcohol moieties will become combined with more than 3 ethylene oxide moieties and an approximately equal proportion will have become combined with less than 3.
  • a typical ethoxylation product mixture there is also a minor proportion of unreacted alcohol.
  • a preferred class of nonionic ethoxylates is represented by the condensation product of a fatty alcohol having from 12 to 15 carbon atoms and from 2 to 9 moles of ethylene oxide per mole of fatty alcohol.
  • Suitable species of this class of ethoxylates include: the condensation product of C12-C15 oxo-alcohols and 7 moles of ethylene oxide; the condensation product of narrow cut C14-C15 oxo-alcohols and 7 or 9 moles of ethylene oxide per mole of fatty (oxo)alcohol; the condensation of a narrow cut C12-C13 fatty (oxo)alcohol and 6.5 moles of ethylene oxide per mole of fatty alcohol.
  • the fatty oxo-alcohols while primarily linear, can have, depending upon the processing conditions and raw material olefins, a certain degree of branching.
  • a degree of branching in the range from 15% to 50% by weight is frequently found in commercially available oxo-alcohols.
  • the amount of alcohol ethoxylate present in the composition of the present invention may range from 15 per cent by weight to 99 per cent by weight, preferably from 25 per cent by weight to 75 per cent by weight, and more preferably from 28 per cent by weight to 66 per cent by weight.
  • the general class of anionic surfactants or alcohol ethoxy­sulfates of relevance to component (b) of the composition is characterized by the chemical formula R′-O- (CH2-CH2O) x -SO3M (II) wherein R′ is a straight-chain or branched-chain alkyl group having in the range of from 8 to 18 carbon atoms, preferably from 2 to 18 carbon atoms, or an alkylaryl group having an alkyl moiety having from 8 to 12 carbon atoms, x represents the average number of oxyethylene groups per molecule and is in the range of from 1 to 12, preferably from 5 to 12 and more preferably from 9 to 12 and M is a cation selected from an alkali metal ion, an ammonium ion, and mixtures thereof.
  • R′ is preferably substantially straight-chain alkyl, that is, at least 50 per cent, preferably about 85 per cent, of the alkyl R′ groups in the instant composition are straight-­ chain. It is understood that R′ can be substituted with any substituent which is inert such as, for example, halo groups.
  • the alcohol ethoxysulfates are derivatives of primary or secondary alcohols of carbon number ranging from 8 to 18.
  • the alcohol precursors of the alcohol ethoxysulfate are straight-chain alcohols or are of a branched-chain structure.
  • Alcohols which are suitable for ethoxylation to form an alcohol ethoxylate which can then be subjected to a sulfation procedure to form the alcohol ethoxysulfate component of the composition include coconut fatty alcohols, tallow fatty alcohols, and the commercially available long-chain synthetic fatty alcohol blends, e.g., the C12 to C15 alcohol blends available as NEODOL 25 Alcohol (Shell Chemical Company), the C12 to C14 alcohol blends available as Tergitol 24L (Union Carbide Corporation), and the C12 to C13 alcohol blends available, for example, as NEODOL 23 Alcohol (Shell).
  • the alcohol ethoxysulfate component is typically prepared by first reacting the alcohol with 1 to 12 moles of ethylene oxide per mole of alcohol to form an alcohol ethoxylate product. Thereafter, these alcohol ethoxylate products are sulfated with a suitable sulfating reagent, and the resulting sulfated product mixture is neutralized with an aqueous alkali metal solution.
  • Suitable sulfation procedures include sulfur trioxide (SO3) sulfation, chlorosulfonic acid (ClSO3H) sulfation and sulfamic acid (NH2SO3H) sulfation, with sulfur trioxide sulfation being preferred.
  • a typical sulfur trioxide sulfation procedure includes contacting liquid alcohol ethoxylate and gaseous sulfur trioxide at about atmospheric pressure in the reaction zone of a falling film sulfator cooled by water at a temperature in the range of from 25 °C to 70 °C to yield the sulfuric acid ester of alcohol ethoxylate. The sulfuric acid ester of the alcohol ethoxylate then exits the falling film column and is neutralized with an alkali metal solution, e.g., sodium or potassium hydroxide, to form the alcohol ethoxysulfate salt.
  • an alkali metal solution e.g., sodium or potassium hydroxide
  • Specific sulfated ethoxylated detergent active compounds which can be used in the composition of the present invention include sulfated ethoxylated fatty alcohols, preferably linear primary or secondary alcohols with C8 to C18, preferably C12 to C15, alkyl groups and an average of 1 to 12, preferably 5 to 12, moles of ethylene oxide per mole of alcohol, and sulfated ethoxylated alkylphenols with C8 to C12 alkyl groups, preferably C8 to C10 alkyl groups and an average of 1 to 12 moles of ethylene oxide per mole of alkylphenol.
  • the preferred class of alcohol ethoxysulfates are the sulfated linear alcohols, such as the C12 to C15 alcohols ethoxylated with an average of from 5 to 12 moles of ethylene oxide.
  • a most preferred alcohol ethoxysulfate is prepared by sulfating a C12-C13 alcohol ethoxylated with 6.5 moles of ethylene oxide.
  • the alcohol ethoxysulfate component has a higher average number of oxyethylene units per molecule than the alcohol ethoxylate component.
  • the average number of oxy­ethylene units per molecule in the alcohol ethoxysulfate component is typically in the range of from 1 to 12, preferably from 5 to 12, and more preferably from 9 to 12, and the average number of oxy­ethylene units per molecule in the alcohol ethoxylate component is typically in the range of from 1 to 12, preferably from 2 to 9, and more preferably from 2 to 5.
  • the amount of alcohol ethoxysulfate present in the composition is in the range of from 1 per cent by weight to 80 per cent by weight, preferably from 25 per cent by weight to 75 per cent by weight, and more preferably from 28 per cent by weight to 66 per cent by weight.
  • the weight ratio of component (a), alcohol ethoxylate, to component (b), alcohol ethoxysulfate can vary widely with weight ratios in the range of from 99:1 to 1:6.
  • the weight ratio of component (a) to component (b) is preferably in the range of from 5:1 to 1:5, more preferably from 3:1 to 1:3, and most preferably from 2:1 to 1:2.
  • Component (c) of the liquid surface active composition is water.
  • the amount of water utilized in the composition is less than 15 per cent by weight of the composition, preferably less than 10 per cent by weight, more preferably less than 7 per cent by weight, and most preferably, less than 5 per cent by weight.
  • the amount of water can be controlled most efficiently when an anhydrous base, such as for example, triethanolamine or mono­ethanolamine, is used as the neutralizing agent.
  • an anhydrous base such as for example, triethanolamine or mono­ethanolamine
  • the amount of water can also be controlled in systems prepared with alkali metal neutralizing agents.
  • the desired amount of water can be readily determined by one of ordinary skill in the art with a minimal amount of routine experimentation.
  • the preparation of the liquid surface active compositions of the invention can be accomplished by mixing the components together in any manner. It is generally preferred, however, that the unneutralized alcohol ethoxysulfate product (i.e., the organic sulfuric acid ester resulting from the sulfation reaction) be added to a well-stirred mixture of alcohol ethoxylate and a concentrated base such as, for example, aqueous 50% sodium hydroxide.
  • a concentrated base such as, for example, aqueous 50% sodium hydroxide.
  • suitable bases include potassium hydroxide, ammonium hydroxide, triethanolamine and monoethanolamine.
  • liquid compositions of the invention have a surface active material content, i.e. the percentage of alcohol ethoxylate plus the percentage of alcohol ethoxysulfate, of at least 85 per cent by weight, preferably at least 90 per cent by weight, and more preferably, at least 95 per cent by weight of said composition.
  • the compositions are also substantially free, typically less than 3 per cent by weight, of organic solvents, preferably alcoholic solvents and more preferably, lower alcoholic solvents having from 1 to 5 carbon atoms.
  • the liquid surfactant compositions of the invention can be utilized in a variety of detergent applications.
  • the liquid surfactant compositions can be adsorbed at relatively low temperatures, about 60 °C or less, onto solid detergent materials such as, for example, sodium carbonate, in order to form dry detergent powders.
  • the liquid surfactant composition can also be added to water to form liquid detergents having lower active matter concentrations.
  • An alcohol ethoxylate with a C12-C13 alkyl group and containing an average of 6.5 moles ethylene oxide/mole alcohol (commercially available as NEODOL 23-6.5 Alcohol) was sulfated by reaction with gaseous SO3 in a lab-scale falling-film reactor to form an alcohol ethoxysulfate.
  • the SO3/ethoxylate molar ratio was 1.05, and the reactor temperature was 65 °C.
  • the acid product was prepared at a rate of 8 g/min and was directly neutralized in a pre-mixed solution containing 16.1 g aqueous 50% sodium hydroxide and 100 g of an alcohol ethoxylate with a C12-C13 alkyl group and containing an average of 5 moles ethylene oxide/mole alcohol (commercially available as NEODOL 23-5 Alcohol).
  • the surfactant mixture was kept well-stirred through the use of a magnetic stirring plate, the temperature of the mixture being maintained at 55 °C with an external water bath. No gel formation was observed throughout the process. Approximately 100 g of acid product from the sulfator were added until pH 8 was obtained as measured by moistened pH paper.
  • the final product was a clear flowable liquid at 20 °C and had the following analyzed composition: - 48% wt Alcohol Ethoxysulfate (Sodium Salt) - 46% wt Alcohol Ethoxylate - 5% wt Water - 1% Sodium Sulfate and trace by-products
  • a viscosity of 0.2 Pa.s was measured for Surfactant Composition A at 50 °C and at a shear rate of 0.42 s ⁇ 1 using a Brookfield Model LVTD viscometer.
  • Table I shows a comparison of the viscosity of Surfactant Composition A with the viscosity of an alcohol ethoxylate/water composition which contains the same amount of alcohol ethoxylate as Surfactant Composition A with the remainder of the composition being water and the viscosity of an alcohol ethoxysulfate/water composition which contains the same amount of alcohol ethoxysulfate as Surfactant Composition A with the remainder of the composition being water.
  • the viscosity of Surfactant Composition A which contains 94 per cent by weight total surfactant, is substantially lower than the viscosity of both the alcohol ethoxylate/water composition and the alcohol ethoxy­sulfate/water composition.
  • Surfactant Composition A Ten g of Surfactant Composition A were mixed with 4.1 g of NEODOL 23-5 Alcohol to produce a liquid which was clear and flowable at 20 °C and which had the following composition: - 34% wt Alcohol Ethoxysulfate (Sodium Salt) - 62% wt Alcohol Ethoxylate - 3% wt Water - ⁇ 1% wt Sodium Sulfate and trace by-products
  • a viscosity of 0.1 Pa.s was measured for the composition at 50 °C and at a shear rate of 0.42 s ⁇ 1.
  • Table II shows a comparison of the viscosity of Surfactant Composition B with the viscosity of an alcohol ethoxylate/water composition which contains the same amount of alcohol ethoxylate as Surfactant Composition B with the remainder of the composition being water and the viscosity of an alcohol ethoxysulfate/water composition which contains the same amount of alcohol ethoxysulfate as Surfactant Composition B with the remainder of the composition being water.
  • the viscosity of Surfactant Composition B which contains 96 per cent by weight total surfactant, is substantially lower than the viscosity of both the alcohol ethoxylate/water composition and the alcohol ethoxy­sulfate/water composition.
  • Surfactant Composition A The procedure described for Surfactant Composition A was used except that 145 g of the acid form of the alcohol ethoxysulfate were neutralized in a pre-mixed solution containing 24 g aqueous 50% sodium hydroxide and 50 g NEODOL 23-5 Alcohol. Twenty g of the product were then blended with 0.7 g of additional NEODOL 23-5 Alcohol to prepare a compositon which was a clear flowable liquid at 35 °C and above and which had the following composition: - 61% wt Alcohol Ethoxysulfate (Sodium Salt) - 32% wt Alcohol Ethoxylate - 6% wt Water - 1% wt Sodium Sulfate and trace by-products
  • a viscosity of 0.7 Pa.s was measured for the composition at 50 °C and at a shear rate of 0.42 s ⁇ 1.
  • Table III shows a comparison of the viscosity of Surfactant Composition C with the viscosity of an alcohol ethoxylate/water composition which contains the same amount of alcohol ethoxylate as Surfactant Composition C with the remainder of the composition being water and the viscosity of an alcohol ethoxysulfate/water composition which contains the same amount of alcohol ethoxysulfate as Surfactant Composition C with the remainder of the composition being water.
  • the viscosity of Surfactant Composition C which contains 93 percent by weight total surfactant, is substantially lower than the viscosity of both the alcohol ethoxylate/water composition and the alcohol ethoxy­sulfate/water composition.
  • Detergent Composition 1 After an aging time of one week, Detergent Composition 1 exhibited an average flow rate of 6.3 g/s thereby falling in the mid-range of the commercial products. By comparison, a powder prepared in the same manner but containing 35 g of NEODOL 23-5 Alcohol as the sole surfactant exhibited a flow rate of 5.4 g/s while a powder prepared with an excessive quantity of NEODOL 23-5 Alcohol (67 g) would not flow through the funnel.
  • Detergent Composition 1 The cleaning properties of Detergent Composition 1 were evaluated using a standard radiolabeled soils' detergency testing procedure which is described in numerous technical articles, e.g. Chemical Times & Trends , Vol. 8, p. 31, and Journal of the American Oil Chemists' Society , Vol. 46, p. 537.
  • Detergent Composition 1 The procedure described for Detergent Composition 1 was used except that 32 g of Surfactant Composition A were added to a powder blend containing 32 g of the sodium bicarbonate/carbonate mixture and 93 g of a light density sodium tripolyphosphate powder. The resulting detergent powder had an average flow rate of 5.0 g/s in the standard funnel flow test after one week aging. Also, the following soil removal levels were found for the detergent composition using the procedure and conditions described above for Detergent Composition 1: Soil % Soil Removal Mineral Oil 28 Synthetic Sebum 60 Clay 34
  • An alcohol ethoxylate with a C12-C13 alkyl group and containing an average of 6.5 moles ethylene oxide/mole alcohol (commercially available as NEODOL 23-6.5 Alcohol) was sulfated by reaction with gaseous SO3 in a lab-scale falling-film reactor to form an alcohol ethoxysulfate.
  • the SO3/ethoxylate molar ratio was 1.05, and the reactor temperature was 65°C.
  • the acid product was prepared at a rate of 8 g/min and was directly neutralized in a pre-mixed solution containing 9.9 g aqueous 50% sodium hydroxide and 150 g of an alcohol ethoxylate with a C12-C13 alkyl group and containing an average of 5 moles ethylene oxide/mole alcohol (commercially available as NEODOL 23-5 Alcohol).
  • the surfactant mixture was kept well-stirred through the use of a magnetic stirring plate, the temperature of the mixture being maintained at 55 °C with an external water bath. No gel formation was observed throughout the process. Approximately 60 g of acid product from the sulfator were added until pH 8 was obtained as measured by moistened pH paper.
  • the final product was a clear flowable liquid at 20°C and had the following analyzed composition: - 28% wt Alcohol Ethoxysulfate (Sodium Salt) - 67% wt Alcohol Ethoxylate - 4% wt Water - 1% Sodium Sulfate and trace by-products
  • Surfactant Composition D The procedure described for Surfactant Composition D was used except that 152 g of the acid form of the alcohol ethoxysulfate were neutralized in a pre-mixed solution containing 27 g aqueous 50% sodium hydroxide and 40g NEODOL 23-5 Alcohol.
  • the final product was a clear flowable liquid at 40 °C and above and had the following analyzed composition: - 69% wt Alcohol Ethoxysulfate (Sodium Salt) - 22% wt Alcohol Ethoxylate - 7% wt Water - 2% wt Sodium Sulfate and trace by-products
  • Detergent Composition 3 exhibited an average flow rate of 6.9 g/s thereby falling in the mid-range of the commercial products.
  • a powder prepared in the same manner but containing 35 g of NEODOL 23-5 Alcohol as the sole surfactant exhibited a flow rate of 5.9 g/s while a powder prepared with an excessive quantity of NEODOL 23-5 Alcohol (67 g) would not flow through the funnel.

Landscapes

  • 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)
EP19900201047 1989-04-26 1990-04-25 Compositions tensio-actives Withdrawn EP0399581A3 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US34323189A 1989-04-26 1989-04-26
US34322789A 1989-04-26 1989-04-26
US343231 1989-04-26
US343227 1989-04-26

Publications (2)

Publication Number Publication Date
EP0399581A2 true EP0399581A2 (fr) 1990-11-28
EP0399581A3 EP0399581A3 (fr) 1990-12-27

Family

ID=26993385

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900201047 Withdrawn EP0399581A3 (fr) 1989-04-26 1990-04-25 Compositions tensio-actives

Country Status (5)

Country Link
EP (1) EP0399581A3 (fr)
JP (1) JPH0362899A (fr)
KR (1) KR900016443A (fr)
PT (1) PT93859A (fr)
TW (1) TW201329B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0431653A2 (fr) * 1989-08-31 1991-06-12 Shell Internationale Researchmaatschappij B.V. Composition liquide tensio-active
WO2006088928A1 (fr) * 2005-02-14 2006-08-24 The Dial Corporation Composition surfactante contenant un sulfate d'alcool-ethoxy destinee a s'utiliser dans des detergents a lessive et processus de fabrication correspondant
WO2009015137A1 (fr) * 2007-07-24 2009-01-29 Shell Oil Company Procédé destiné à fabriquer un produit nettoyant à base d'alcool secondaire

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW391981B (en) * 1996-12-02 2000-06-01 Kao Corp Surfactant formulation
JP4772415B2 (ja) * 2004-08-06 2011-09-14 花王株式会社 単核性洗剤粒子群の製造方法
JP4965821B2 (ja) * 2005-06-08 2012-07-04 花王株式会社 界面活性剤組成物
JP6155133B2 (ja) * 2012-08-29 2017-06-28 ライオン株式会社 液体洗浄剤

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2135214A1 (fr) * 1971-05-04 1972-12-15 Colgate Palmolive Co
FR2189505A1 (fr) * 1972-06-23 1974-01-25 Colgate Palmolive Co
FR2193872A1 (fr) * 1972-07-20 1974-02-22 Colgate Palmolive Co
EP0265203A1 (fr) * 1986-10-20 1988-04-27 Unilever Plc Compositions détergentes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2135214A1 (fr) * 1971-05-04 1972-12-15 Colgate Palmolive Co
FR2189505A1 (fr) * 1972-06-23 1974-01-25 Colgate Palmolive Co
FR2193872A1 (fr) * 1972-07-20 1974-02-22 Colgate Palmolive Co
EP0265203A1 (fr) * 1986-10-20 1988-04-27 Unilever Plc Compositions détergentes

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
(HENKEL) *
PATENT ABSTRACTS OF JAPAN *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0431653A2 (fr) * 1989-08-31 1991-06-12 Shell Internationale Researchmaatschappij B.V. Composition liquide tensio-active
EP0431653A3 (en) * 1989-08-31 1993-03-10 Shell Internationale Research Maatschappij B.V. Liquid surface active compositions
WO2006088928A1 (fr) * 2005-02-14 2006-08-24 The Dial Corporation Composition surfactante contenant un sulfate d'alcool-ethoxy destinee a s'utiliser dans des detergents a lessive et processus de fabrication correspondant
WO2006089013A1 (fr) * 2005-02-14 2006-08-24 The Dial Corporation Composition de detergent amelioree presentant un plus grand pouvoir blanchissant
US7754669B2 (en) 2005-02-14 2010-07-13 The Dial Corporation Detergent composition with enhanced whitening power
WO2009015137A1 (fr) * 2007-07-24 2009-01-29 Shell Oil Company Procédé destiné à fabriquer un produit nettoyant à base d'alcool secondaire
US20110092406A1 (en) * 2007-07-24 2011-04-21 Kirk Herbert Raney Process for making a secondary alcohol cleaning product

Also Published As

Publication number Publication date
JPH0362899A (ja) 1991-03-18
KR900016443A (ko) 1990-11-13
TW201329B (fr) 1993-03-01
EP0399581A3 (fr) 1990-12-27
PT93859A (pt) 1990-11-20

Similar Documents

Publication Publication Date Title
US4464292A (en) Mixed ethoxylated alcohol/ethoxy sulfate surfactants and synthetic detergents incorporating the same
US4240921A (en) Liquid cleaning concentrate
US5922670A (en) Dimeric alcohol-bis and trimeric alcohol-tris-sulphates and ether sulphates thereof
US4207421A (en) Biodegradable, alkali stable, non-ionic surfactants
EP0238638B1 (fr) Procede de preparation d'une composition detergente particulaire
JPH064878B2 (ja) エタノ−ルを含まない液体洗濯洗剤組成物
US4668423A (en) Liquid biodegradable surfactant and use thereof
US4438014A (en) Nonionic surfactants for automatic dishwasher detergents
EP0482687A1 (fr) Composition coulable liquide concentrée
US3168478A (en) Highly alkaline surface active compositions
AU652812B2 (en) Process for preparing a liquid surfactant composition
US3501409A (en) Detergent-hydrotrope composition
US4792419A (en) Ether sulfonates
US5215683A (en) Highly concentrated liquid surface active compositions containing alcohol ethoxylate and alcohol ethoxysulfate
US5209874A (en) Liquid surface active compositions
KR970011314B1 (ko) (a) 술폰화된 불포화 지방산의 알칼리, 암모늄 및/또는 아민염과 (b) 알콕시화 알킬 및/또는 알켄일 알코올 및/또는 술포숙신산 에스테르를 함유하는 혼합물의 습식제로서의 용도
EP0399581A2 (fr) Compositions tensio-actives
US2932616A (en) Detergent compositions
US3959186A (en) Process for manufacturing detergent builders
EP0431653A2 (fr) Composition liquide tensio-active
US4855075A (en) Ethoxylates of alkyl and alkenyl catechols
US4412945A (en) Aqueous high concentration slurry of alcohol ethoxylate
CA1083910A (fr) Production de detergents
US4436642A (en) Nonionic surfactants for automatic dishwasher detergents
US5158692A (en) Wetting agents for use in aqueous alkaline treatment preparation for yarns or sheet-form textiles

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): BE DE ES FR GB IT NL SE

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): BE DE ES FR GB IT NL SE

17P Request for examination filed

Effective date: 19910418

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Withdrawal date: 19930225