WO2014095793A1 - Utilisation d'un alcool éthoxylé en tant qu'hydrotrope pour un adduit d'oxyde d'alkylène d'un alcool - Google Patents

Utilisation d'un alcool éthoxylé en tant qu'hydrotrope pour un adduit d'oxyde d'alkylène d'un alcool Download PDF

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Publication number
WO2014095793A1
WO2014095793A1 PCT/EP2013/076812 EP2013076812W WO2014095793A1 WO 2014095793 A1 WO2014095793 A1 WO 2014095793A1 EP 2013076812 W EP2013076812 W EP 2013076812W WO 2014095793 A1 WO2014095793 A1 WO 2014095793A1
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Prior art keywords
alcohol
alkylene oxide
oxide adduct
weight ratio
composition
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PCT/EP2013/076812
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English (en)
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Camilla NYSTRÖM
Anette Thyberg
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Akzo Nobel Chemicals International B.V.
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Publication of WO2014095793A1 publication Critical patent/WO2014095793A1/fr

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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • C11D1/8255—Mixtures of compounds all of which are non-ionic containing a combination of compounds differently alcoxylised or with differently alkylated chains
    • 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
    • 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
    • C11D1/721—End blocked ethers
    • 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
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups

Definitions

  • the present invention relates to the use of an ethoxylated alcohol as a hydrotrope for an alkylene oxide adduct of an alcohol in aqueous solutions. It also relates to a composition comprising said ethoxylated alcohol and said alkylene oxide adduct, and the use of this composition for the cleaning of hard surfaces.
  • aqueous solution to spread evenly over a surface, the so-called wetting ability, is important for many applications.
  • a composition for the cleaning of hard surfaces benefits from a good wetting of the surface.
  • Nonionic surfactants that are alkylene oxide adducts of alcohols, also referred to as alcohol alkoxylates, are known to be good wetting agents, and are often present in compositions for the cleaning of hard surfaces.
  • the compositions may further contain alkaline or acidic components, such as alkaline or acidic chelating agents, or neutral salts.
  • alkaline or acidic components such as alkaline or acidic chelating agents, or neutral salts.
  • many alcohol alkoxylates with good wetting properties are not soluble enough in aqueous solutions, and therefore need the presence of a hydrotrope to improve their solubility.
  • a hydrotrope is defined as a compound that solubilizes hydrophobic compounds in aqueous solutions, in particular a compound that improves the solubility of surfactants in water. Hydrotropes are sometimes also called e.g. solubilizers, couplers, compatibility agents or co-surfactants. A good hydrotrope is not necessarily a good wetting agent. Its main task is to enhance the solubility of the surfactant, and thereby increase the wetting ability of the composition. For alcohol alkoxylates this will be manifested in an increased cloud point of the composition as compared to a composition without the hydrotrope. A number of hydrotropes for alcohol alkoxylates have been described in various publications.
  • hydrotropes examples include ethanol, sodium xylene sulphonate, sodium cumene sulphonate, alkyl glycosides, alkoxylated quaternary ammonium compounds, and phosphated alkoxylated alcohols.
  • US 2012/0102668 A1 relates to a thickened liquid hard surface cleaning composition
  • a thickened liquid hard surface cleaning composition comprising an alkoxylated non-ionic surfactant, a sulphated or sulphonated anionic surfactant and a neutralizing co-surfactant, such as an amine oxide surfactant and a betaine surfactant.
  • EP 0 616 027 relates to concentrated cleaning compositions, primarily for hard surfaces, comprising from 10 to 80% by weight of the total composition of water and at least one short chain surfactant comprising a C 6 - C 0 alkyl chain as its hydrophobic portion, such as a non-ionic surfactant and/or an alkyl sulphonate.
  • GB 2 204 321 A relates to a biodegradable liquid detergent composition containing a fatty alcohol polyethylene glycol ether, an alkanolamine, a sequestering agent and a fatty alcohol polyethylene/polypropylene glycol ether.
  • JP 2010-143971 relates to a detergent composition and method for cleaning a liquid crystal panel, which composition includes organic alkali, e.g. an alkanolamine; a hydrocarbon, and a surfactant selected from a group consisting of a polyoxyalkylene alkyl ether and a sulfosuccinic acid-type anionic surfactant.
  • organic alkali e.g. an alkanolamine
  • hydrocarbon e.g. an alkanolamine
  • a surfactant selected from a group consisting of a polyoxyalkylene alkyl ether and a sulfosuccinic acid-type anionic surfactant.
  • JP 2009-084621 relates to metal detergent composition comprising two specific types of non-ionic surfactants
  • WO 2007/064673 and US 8, 1 19,585 B2 relate to a high actives liquid non-ionic surfactant concentrate that includes a fatty alcohol alkoxylate having an alkylene oxide content of about 10-100 moles and at least one other non-ionic surfactant alkoxylate having an alkylene oxide content of about 4-12 moles.
  • the liquid surfactant concentrate may be utilized in e.g. emulsion polymerization or in the formulation of agrochemical compositions, and also as emulsifier for solvents in cleaning compositions.
  • US 6,342,474 B1 relates to an aqueous hard surface cleaning composition
  • a water soluble organic solvent comprising a non-ionic surfactant selected from the group consisting of an alcohol alkoxylate, an alcohol block alkoxylate, a polyoxyethylene polyoxypropylene block surfactant, and mixtures thereof, a cleaning auxiliary and optionally a thickening agent.
  • EP 0 681 865 A2 relates to a low-foaming wetting agent useful for e.g. textile processes and plant protection formulations, which comprises a combination of several types of alkyl ethoxylates, alkyl ethoxylates/propoxylates and alkyl propoxylates.
  • WO 2007/096292 relates to a surfactant mixture containing an alkoxylation product of alkanols having 8 to 12 carbon atoms and 3 to 30 alkoxy groups per alkanol group, where the alkanols have a mean degree of branching of at least 1 , and an alkoxylation product of alkanols having 13 to 20 carbon atoms and 3 to 30 alkoxy groups per alkanol group, where the alkanols have a mean degree of branching of 0.0 to 0.3.
  • These surfactant mixtures may be used in formulations for e.g. hard surface cleaning.
  • WO 03/091 190 relates to an alkoxylate mixture of at least one alkoxylate having a hydrocarbyl group with 8 to 1 1 carbon atoms, alkoxylated with 1 to 20 ethyleneoxy groups and 0 to 10 C 3 -C 10 alkyleneoxy groups, and at least one alkoxylate having a hydrocarbyl group with 12 to 24 carbon atoms, alkoxylated with 1 to 50 ethyleneoxy groups and 0 to 10 C 3 -C 0 alkyleneoxy groups.
  • the alkoxylate mixture is claimed to be useful for detergents for the cleaning of textiles.
  • the invention relates to the use of an ethoxylated alcohol as a hydrotrope for an alkylene oxide adduct of an alcohol in aqueous solutions.
  • the invention relates to an aqueous composition comprising the ethoxylated alcohol and an alkylene oxide adduct of an alcohol.
  • the invention relates to the use of the composition in a method for the cleaning of hard surfaces.
  • hydrotrope will be referred to as the "ethoxylated alcohol” and the non-ionic compound that is solubilised by the hydrotrope will be referred to as the "alkylene oxide adduct of an alcohol”.
  • the ethoxylated alcohol i.e. the hydrotrope, has the formula RO(EO) b Y (I), wherein R is a hydrocarbyl group having 8-12, preferably 8-1 1 , and most preferably 8-10, carbon atoms, EO is an ethyleneoxy unit, b is at least 10, preferably at least 11 , more preferably at least 12, even more preferably at least 13, still more preferably at least 14, still more preferably at least 15, and most preferably at least 16, and at most 35, preferably at most 34, more preferably at most 33, even more preferably at most 32, still more preferably at most 31 , still more preferably at most 30, and most preferably at most 25; and Y is H, -R 1 or -C(0)R 1 where R 1 is a C1 -C4 alkyl group.
  • Y is H.
  • the hydrocarbyl group of the ethoxylated alcohols may be linear or branched, saturated or unsaturated.
  • Suitable examples of the ethoxylated alcohols are n- octanol ethoxylated with from 10 to 35 moles of EO (ethylene oxide) per mole of n- octanol, 2-ethylhexanol ethoxylated with from 10 to 35 moles of EO per mole of 2- ethylhexanol, n-decanol ethoxylated with from 10 to 35 moles of EO per mole of n- decanol, 2-propylheptanol ethoxylated with from 10 to 35 moles of EO per mole 2- propylheptanol, and n-dodecanol ethoxylated with from 10 to 35 moles of EO per mole of n-dodecanol.
  • EO ethylene oxide
  • the products based on the ethoxylated alcohols are in general easy to work with when making solutions in water.
  • the ethoxylated dodecanol products there is a problem with gelation when concentrated solutions are made.
  • the products (I) having a C 8 to Cn hydrocarbyl group are more preferred than the compounds having a C 2 hydrocarbyl group.
  • the alkylene oxide adduct of an alcohol preferably has an HLB value according to Davies (Tenside Surfactants Detergents 29 (1992) p. 2) of at most 8.0, preferably at most 7.5.
  • the formula for the alkylene oxide adduct of an alcohol is
  • R 2 is a C 8 to C 12, preferably C 8 to Cn, hydrocarbyl group
  • AO is a C3-C10 alkyleneoxy unit, preferably a propyleneoxy unit
  • EO is an ethyleneoxy unit
  • x 0-4, preferably 0-2, and most preferably 0
  • y is at least 1 , preferably at least 2, more preferably at least 3, and most preferably at least 4, and is at most 9, preferably at most 8, more preferably at most 7, and most preferably at most 6
  • z 0—4, preferably 0-2, and most preferably 0
  • Y is H, -R 1 or -C(0)R 1 , where R 1 is a C1 -C4 alkyl group.
  • Y is preferably H.
  • the C 8 -C 12 -alcohol alkoxylates may also contain e.g. up to 4 propyleneoxy (PO) units.
  • the number of propyleneoxy units, when present, may be as small as 0.1 mole PO per mole alcohol.
  • the ethyleneoxy units and the alkyleneoxy units may be added randomly or in blocks. The blocks may be added to the alcohol in any order.
  • the alcohol ethoxylates may be end-capped with the group Y (when Y is not H), but products that are not end-capped (Y is H) are preferred.
  • the hydrocarbyl group of the alcohol alkoxylates may be linear or branched, saturated or unsaturated.
  • the ethoxylated alcohol (I) and the alkylene oxide adducts of an alcohol (II) may be produced by procedures well-known in the art using e.g. a conventional basic catalyst, such as KOH, or a so-called narrow range catalyst (see e.g. Nonionic Surfactants: Organic Chemistry in Surfactant Science Series volume 72, 1998, pp 1 - 37 and 87-107, edited by Nico M. van Os; Marcel Dekker, Inc).
  • a conventional basic catalyst such as KOH
  • narrow range catalyst see e.g. Nonionic Surfactants: Organic Chemistry in Surfactant Science Series volume 72, 1998, pp 1 - 37 and 87-107, edited by Nico M. van Os; Marcel Dekker, Inc.
  • Suitable alkylene oxide adducts of an alcohol having a linear hydrocarbyl group include C 9 -Cn alcohol + 4, 5, 6, 7 or 8 EO, and Cn alcohol + 3, 4, 5, 6, 7 or 8 EO.
  • Suitable alkylene oxide adducts of an alcohol having a branched hydrocarbyl group include 2-ethylhexanol + 3, 4 or 5 EO, 2-ethylhexanol + 2 PO + 4, 5 or 6 EO, 2- propylheptanol + 3, 4, 5 or 6 EO and 2-propylheptanol + 1 PO + 4 EO.
  • Another example is 2-butyloctanol + 5, 6 or 7 EO. Wherever the degree of alkoxylation is discussed, the numbers referred to are molar average numbers, essentially corresponding to the reaction of the indicated number of moles of alkylene oxide with one (1 ) mole of alcohol.
  • the composition normally will contain a salt of some kind, such as alkaline or acidic chelating agents, also called complexing agents or sequestering agents, or neutral salts.
  • the amounts of the components in the aqueous composition are suitably:
  • At least 0.05 preferably at least 0.5, and most preferably at least 1 % by weight, and at most 60, preferably at most 50, more preferably at most 40, even more preferably at most 30, still more preferably at most 20, still more preferably at most 15, and most preferably at most 10% by weight, of the alkylene oxide adduct of an alcohol (II); and Hi) 0, preferably at least 0.05, most preferably at least 0.1 % by weight, and at most 20 preferably at most 15, and most preferably at most 10% by weight, of a chelating agent or other salt.
  • aqueous compositions may either be concentrates that could be used as such, or that should be diluted before use.
  • the ethoxylated alcohol (I) and the alkylene oxide adduct of an alcohol (II) could be premixed in a highly concentrated composition comprising water as a solvent.
  • a premix concentrate suitably contains 30-60% by weight of ethoxylated alcohol (I), 30- 60% by weight of alkylene oxide adduct of an alcohol (II), and normally at least 10% water. This composition is suitable for bulk transportation, since the amount of water is rather low.
  • a chelating agent or any other salt should be present in the composition, it may suitably be added to the water before the premix and water are mixed, but it could equally well be added afterwards.
  • the less concentrated aqueous composition could also be produced by adding the desired amounts of the components separately, in any order.
  • iii) 0%, preferably at least 0.1 , more preferably at least 0.5, even more preferably at least 1 , still more preferably at least 2, still more preferably at least 3, still more preferably at least 4, and most preferably at least 5% by weight, and at most 10% by weight of a chelating agent Concentrates having higher amounts of the components are also possible to produce if needed.
  • a typical dilution would be from 1 :5 to 1 :30 with water, but depending on the initial concentration of the composition, dilutions of up to 1 :50 or even up to 1 :200 with water may also be made.
  • a typical diluted composition comprising a chelating agent
  • the amounts of the components are suitably 0.1 -1 % by weight of i), 0.1 -1 % by weight of ii) and 0.05-1 % by weight of iii).
  • compositions of the present invention are suitably clear and homogeneous, preferably up to a temperature of at least 40°C, i.e. the cloud point of compositions comprising the alkylene oxide adduct of an alcohol should suitably be at least 40°C.
  • the cloud point may be adapted by changing the weight ratio of ethoxylated alcohol (I) to alkylene oxide adduct of an alcohol (II). This ratio is within the range 1 :20 to 2:1 , typically 1 :5 to 1.5:1.
  • the weight ratio between the ethoxylated alcohol (I) and the chelating agent/other salt suitably is within the range 1 :50 to 20: 1 , typically 1 :10 to 10:1 .
  • the weight ratio between alkylene oxide adduct of an alcohol (II) and the chelating agent is normally within the range 1 : 10 to 10:1 , typically 1 :5 to 5: 1 .
  • the consumer concentrates normally contains at least 50% by weight of water, suitably at least 70% by weight, and normally at most 95% by weight of water, suitably at most 90% by weight.
  • Aqueous cleaning compositions in accordance with the invention may further contain other hydrotropes and other surfactants, such as anionic surfactants, cationic surfactants, amphoteric surfactants and/or amine oxides: and conventional additives, such as (but not limited to) alkali, such as sodium hydroxide or potassium hydroxide, silicates, acids, solvents, other salts, perfumes, pH buffers, abrasives, soil antiredeposition agents, preservatives, opacifiers, disinfectants, deodorants, colorants, corrosion inhibitors, foam regulators and rheology modifiers, such as polymers; in the usual amounts.
  • alkali such as sodium hydroxide or potassium hydroxide
  • silicates such as sodium hydroxide or potassium hydroxide
  • acids such as sodium hydroxide or potassium hydroxide
  • acids such as sodium hydroxide or potassium hydroxide
  • perfumes such as sodium hydroxide or potassium hydroxide
  • silicates such as sodium hydroxide or potassium hydrox
  • the weight ratio between the solvent and the sum of (I) and (II) is lower than 1 : 10, preferably lower than 1 :20. Most preferably the compositions are substantially or totally free from hydrocarbon solvents. If anionic surfactants are present, the weight ratio between the anionic surfactant and the alkylene oxide adduct of an alcohol (II) is less than 1 :4, more preferably less than 1 : 10, and even more preferably less than 1 :20. Most preferably the compositions are substantially or totally free from anionic surfactants.
  • the weight ratio between the amine oxide and the alkylene oxide adduct of an alcohol (II) is less than 1 :4, preferably less than 1 : 10, and more preferably less than 1 :20. Most preferably the compositions are substantially or totally free from amine oxides.
  • the term "substantially free from”, e.g. as in substantially free from a compound, e.g hydrocarbon solvents, anionic surfactants and/or amine oxides, shall be interpreted as that no such compound has been added purposively to the composition. However, trace amounts of such compound, such as coming from impurities etc, may be present in the compostion.
  • compositions may be acidic, neutral or alkaline.
  • Alkaline compositions typically comprise alkaline chelating agents.
  • Alkanolamines such as monoethanolamine MELA, diethanolamine (DEA) and triethanolamine (TEA), which are sometimes used as a source of alkalinity, are however not contemplated for use as components in the present compositions, and the compositions are thus substantially free from alkanolamines.
  • chelating agents may also be added, such as citric acid.
  • the cleaning compositions of the invention are suitably alkaline.
  • the compositions of the present invention were found to be at least as efficient as comparative compositions containing sodium xylene sulfonate as hydrotrope instead of the ethoxylated alcohol.
  • the cleaning efficiency of the compositions is very good even at high dilutions of the compositions. Further, their biodegradability is good and the toxicity low.
  • compositions are excellent for use in cleaning hard surfaces, such as for vehicle cleaning and household cleaning.
  • another aspect of the invention is a method for the cleaning of hard surfaces, which comprises the steps of adding to said surfaces a cleaning effective amount of a composition as described above, and thereafter rinsing and/or wiping the said surfaces.
  • One further aspect of the invention is a general method for raising the cloud point of a composition comprising an alkylene oxide adduct of an alcohol, by adding an effective amount of an ethoxylated alcohol as defined above.
  • the cloud point of a fluid is the temperature at which dissolved solids are no longer completely soluble, precipitating as a second phase giving the fluid a cloudy appearance.
  • NR synthetic primary alcohol with >80 % linearity, narrow range (NR) ethoxylated with 5.5 moles of ethyleneoxide (EO) per mole alcohol.
  • NR synthetic primary alcohol with >80 % linearity, narrow range (NR) ethoxylated with 4 moles of ethyleneoxide (EO) per mole alcohol. All narrow range ethoxylated alcohols are abbreviated in the same manner.
  • Aqueous formulations with the ethoxylated alcohol hydrotropes specified in Table 1 were made. All compositions contain 5% of a 1 : 1 mixture of a C 9 -C 1 alcohol + 5.5EO (NR) and a C 9 -C 1 alcohol + 4EO (NR); and 10% (4.7% a.s.) of Dissolvine GL-47S (Active ingredient is L-glutamic acid-N,N-diacetic acid tetrasodium salt; GLDA) (ex AkzoNobel).
  • the amount of hydrotrope in Table 1 was the amount needed to obtain a solution having the cloud point indicated in the Table.
  • the cloud points in the Table are given as °C.
  • compositions only differing in the amount of hydrotrope needed for achieving the desired cloud point, the following method was used.
  • the final solutions should all weigh 100g. In this solution there should be included X g of alcohol alkoxylate and Y gram of chelating agent.
  • Step 1 Y gram of chelating agent is dissolved in 75 g of water.
  • Step 2 X gram of alcohol alkoxylate is added to this solution.
  • Step 3 The mixture obtained in step 2 is heated to the desired cloud point.
  • Step 4 Hydrotrope is added dropwise at this temperature until a clear solution is obtained.
  • Step 5 Water is added in such an amount that the whole mixture weighs 99 g. Step 6. The cloud point is measured.
  • step 3 If the cloud point has not changed from the desired value in step 3, 1 g water is added, and the composition is ready.
  • the soiled tiles may be kept up to 5 days at room temperature before use.
  • Active ingredient is L-glutamic acid-N,N-diacetic acid tetrasodium salt
  • Formulation 6 containing an ethoxylated alcohol hydrotrope (I) according to the invention, an alkylene oxide adduct of an alcohol (II), and a chelating agent, was much more effective in cleaning the plates at the dilution 1 :20 than the diluted comparison formulation 4, which contained only the hydrotrope, and the diluted formulation 5, which contained the hydrotrope and the chelating agent.

Abstract

La présente invention concerne l'utilisation d'un alcool éthoxylé ayant la formule RO(EO)bY (I) dans laquelle R est un groupe hydrocarbyle ayant 8 à 11 atomes de carbone, EO est un motif éthylénoxy, b = 11 à 35, et Y est H, -R1 ou -C(O)R1, où R1 est un groupe alkyle en C1-C4 ; en tant qu'hydrotrope pour un adduit d'oxyde d'alkylène d'un alcool dans des solutions aqueuses. La présente invention concerne en outre une composition comprenant ledit alcool éthoxylé (I) et ledit adduit d'oxyde d'alkylène d'un alcool, et l'utilisation de cette composition pour le nettoyage de surfaces dures.
PCT/EP2013/076812 2012-12-19 2013-12-17 Utilisation d'un alcool éthoxylé en tant qu'hydrotrope pour un adduit d'oxyde d'alkylène d'un alcool WO2014095793A1 (fr)

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US201261739131P 2012-12-19 2012-12-19
US61/739,131 2012-12-19
EP12198174 2012-12-19
EP12198174.0 2012-12-19

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EP2963101A1 (fr) * 2014-07-04 2016-01-06 Kolb Distribution Ltd. Agents de nettoyage pour surfaces dures
WO2018078601A1 (fr) * 2016-10-31 2018-05-03 SABIC Global Technologies B.V Éthoxylate du 2-éthylhexanol utilisé comme hydrotrope dans des détergents liquides
US10022691B2 (en) 2015-10-07 2018-07-17 Elementis Specialties, Inc. Wetting and anti-foaming agent
US10947480B2 (en) 2016-05-17 2021-03-16 Conopeo, Inc. Liquid laundry detergent compositions

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EP2963100A1 (fr) * 2014-07-04 2016-01-06 Kolb Distribution Ltd. Compositions aqueuses de rinçage
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US11052361B2 (en) 2015-10-07 2021-07-06 Elementis Specialties, Inc. Wetting and anti-foaming agent
US11634643B2 (en) 2015-10-07 2023-04-25 Elementis Specialties, Inc. Wetting and anti-foaming agent
US10947480B2 (en) 2016-05-17 2021-03-16 Conopeo, Inc. Liquid laundry detergent compositions
US11572529B2 (en) 2016-05-17 2023-02-07 Conopeo, Inc. Liquid laundry detergent compositions
WO2018078601A1 (fr) * 2016-10-31 2018-05-03 SABIC Global Technologies B.V Éthoxylate du 2-éthylhexanol utilisé comme hydrotrope dans des détergents liquides
CN109906266A (zh) * 2016-10-31 2019-06-18 沙特基础工业全球技术有限公司 作为液体洗涤剂中的助水溶物的2-乙基己醇乙氧基化物
US11332696B2 (en) 2016-10-31 2022-05-17 Sabic Global Technologies B.V. 2-ethylhexanol ethoxylate as a hydrotrope in liquid detergents
CN109906266B (zh) * 2016-10-31 2023-09-01 沙特基础工业全球技术有限公司 作为液体洗涤剂中的助水溶物的2-乙基己醇乙氧基化物

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