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EP4630524A1 - Compositions de nettoyage hydrotropiques - Google Patents

Compositions de nettoyage hydrotropiques

Info

Publication number
EP4630524A1
EP4630524A1 EP22839999.4A EP22839999A EP4630524A1 EP 4630524 A1 EP4630524 A1 EP 4630524A1 EP 22839999 A EP22839999 A EP 22839999A EP 4630524 A1 EP4630524 A1 EP 4630524A1
Authority
EP
European Patent Office
Prior art keywords
less
cleaning composition
hydrotrope
surfactant
foam
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.)
Pending
Application number
EP22839999.4A
Other languages
German (de)
English (en)
Inventor
Cheng Shen
Tao Wang
Chen Zheng
Xiaolin Ma
Dan Jiang
Jieying Chen
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.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
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 Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Publication of EP4630524A1 publication Critical patent/EP4630524A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof

Definitions

  • the present disclosure is related to cleaning compositions and more specifically to cleaning compositions that comprise a hydrotrope.
  • hydrotropes are compounds which enable the solubilization of surfactants into a formulation at a higher concentration than the formulation would typically support. Hydrotropes are useful materials because under certain circumstances, such as high alkalinity (i.e., 10 weight percent ( “wt%” ) of NaOH in the cleaning formulation or even higher) the solubility of a surfactant in a cleaning composition is low.
  • the low solubility of the surfactant in the cleaning composition means that not only may the cleaning composition not have sufficient detergency due to low surfactant loading, but also may exhibit a hazy appearance (due to insolubility of the surfactant in the formulation) , phase separation and instability.
  • hydrotropes can be thought of as a coupling or solubilization agent between the surfactant and cleaning composition.
  • a measurement for how well a hydrotrope couples a non-ionic surfactant (the type of surfactant most common in industrial cleaning formulations) to an alkaline composition is the amount of hydrotrope required to impart a cloud point increase to the cleaning composition.
  • a hydrotrope would be considered successful in coupling if a 1 wt%nonionic surfactant solution having an initial cloud point at 35°C in a 5 wt%NaOH water solution at 23°Cis transformed from hazy (i.e., not soluble) to clear with just the addition of 2.5 wt%the hydrotrope.
  • Hydrotropes may also affect other properties of the cleaning composition.
  • some hydrotropes are known to produce stable foams which are typically not advantageous in industrial cleaning settings.
  • some alkyl polyglucosides can be used for hydrotropes, but as United States Patent No 3,219,656 explains that alkyl polyglucosides “show high stable foams and which act as foam stabilizers for other surfactants. ”
  • Stable foams in industrial cleaning applications present problems due to additional rinsing time and water consumption as well as the foam interfering with the machinery of the cleaning system.
  • the Ross-Miles Foam Height test is a standard foam test method for amphiphilic materials where a water solution of surfactant or hydrotrope sample is poured into the test tube and its initial height of any foam is compared against the height of the foam after 5 minutes of allowing the foam to dissipate.
  • a surfactant or hydrotrope exhibiting an initial foam height (at 0.1 wt%aqueous solution) less than 50 mm and a foam height less than 20 mm after 5 minutes are considered to be low foam surfactant or hydrotrope.
  • hydrotropes An additional, and increasingly important trend is the switch to environment-friendly hydrotropes. It is an increasing consideration of cleaning solution manufacturers is that components utilized in the cleaning solution be eco-friendly and biodegradable.
  • Traditional hydrotropes include phosphate type and (di) sulfonate type, both of which are coming under increasing scrutiny. For example, phosphorus containing hydrotropes are alleged to result in increased eutrophication of water ways while some of sulfonate type hydrotropes are not readily biodegradable, or strong eye/skin irritation.
  • the inventors of the present application have discovered a cleaning composition utilizing an alkyl polyglucoside hydrotrope that not only is successful under the guidelines laid out above, but also exhibits less than 50 mm of initial foam and less than 20 mm of foam after 5 minutes when tested at 0.1 wt%according to the Ross-Miles Foam Height Test and is readily biodegradable.
  • m is from 1.0 to 1.2.
  • alkyl glucosides are typically used in applications where high and stable foam is desired.
  • the branched alkyl 2-octanol in Structure (I) with an m from 1.0-1.2 exhibits 10 mm of initial foam and 0 mm of foam after 5 minutes when tested at 0.1 wt%according to the Ross-Miles Foam Height Test.
  • the lightly branched nature of Structure (I) renders the hydrotrope unable to stabilize foams generated by agitation of cleaning compositions including the hydrotrope.
  • the low m value in combination with the 2-octyl of Structure (I) is also believed to place the hydrophilic-lipophilic balance of the hydrotrope at a value which provides superior cloud point increase rending the hydrotrope a successful in solubilizing and coupling the surfactant to the cleaning composition.
  • the use of the alkyl glucoside hydrotrope does not negatively impact the biodegradability and eco-friendly nature of cleaning compositions it is added to as compared to phosphate or sulfonate hydrotropes.
  • a cleaning composition comprises water, a surfactant and a hydrotrope having Structure (I) wherein m of Structure (I) is from 1.0 to 1.2 as measured according to 13 C Nuclear Magnetic Resonance.
  • the surfactant is a non-ionic surfactant.
  • the cleaning composition comprises from 0.01 wt%to 10.0 wt%of the surfactant based on a total weight of the cleaning composition.
  • the cleaning composition comprises an alkali salt.
  • the cleaning composition comprises 0.1 wt%of NaOH or greater based on a total weight of the cleaning composition.
  • the cleaning composition comprises from 0.01 wt%to 20.0 wt%of the hydrotrope.
  • the cleaning composition comprises from 0.5 wt%to 10.0 wt%of the hydrotrope based on a total weight of the cleaning composition.
  • the term “and/or, ” when used in a list of two or more items, means that any one of the listed items can be employed by itself, or any combination of two or more of the listed items can be employed.
  • the composition can contain A alone; B alone; C alone; A and B in combination; A and C in combination; B and C in combination; or A, B, and C in combination.
  • weight percent designates the percentage by weight a component is of a total weight of the glycol composition unless otherwise specified.
  • Chemical Abstract Services registration numbers refer to the unique numeric identifier as most recently assigned as of the priority date of this document to a chemical compound by the Chemical Abstracts Service.
  • the cleaning composition of the present disclosure comprises water, a surfactant, and a hydrotrope having Structure (I) :
  • the cleaning composition comprises from 70 wt%to 90 wt%water based on the total weight of the cleaning composition.
  • the cleaning composition may comprise 70 wt%or greater, or 72 wt%or greater, or 74 wt%or greater, or 76 wt%or greater, or 78 wt%or greater, or 80 wt%or greater, or 82 wt%or greater, or 84 wt%or greater, or 86 wt%or greater, or 88 wt%or greater, or 90 wt%or greater, or 92 wt%or greater, or 94 wt%or greater, or 96 wt%or greater, or 98 wt%or greater, while at the same time, 99 wt%or less, or 98 wt%or less, or 96 wt%or less, or 94 wt%or less, or
  • the cleaning composition comprises a surfactant.
  • surfactant means a material that is capable of lowering the interfacial energy between two dissimilar substances.
  • the surfactant may be an anionic surfactant, a non-ionic surfactant, a cationic surfactant, an amphoteric surfactant and/or combinations thereof.
  • the hydrophobic portion of the surfactant may be branched or linear, primary alkyl or secondary alkyl, saturated or unsaturated, or (multi) -aryl-containing alkyl.
  • the surfactant may be a branched alcohol ethoxylate.
  • a commercially available example of the surfactant may include ECOSURF TM LFE-635 from The Dow Chemical Company, Midland, MI; or a broadly commercially available example of primary C12-14 alcohol ethoxylate, such as TERGITOL TM 26-L-9.
  • the cleaning composition may comprise from 0.01 wt%to 10.0 wt%of the surfactant based on a total weight of the cleaning composition.
  • the cleaning composition may comprise 0.01 wt%or greater, or 0.1 wt%or greater, or 0.5 wt%or greater, or 1.0 wt%or greater, or 1.5 wt%or greater, or 2.0 wt%or greater, or 2.5 wt%or greater, or 3.0 wt%or greater, or 3.5 wt%or greater, or 4.0 wt%or greater, or 4.5 wt%or greater, or 5.0 wt%or greater, or 5.5 wt%or greater, or 6.0 wt%or greater, or 6.5 wt%or greater, or 7.0 wt%or greater, or 7.5 wt%or greater, or 8.0 wt%or greater, or 8.5 wt%or greater, or 9.0 wt%or greater, or 9.5 wt%or greater, while at the same time
  • the cleaning composition comprises the hydrotrope having Structure (I) :
  • m of Structure (I) is from 1.0 to 1.2 as measured according to 13 C Nuclear Magnetic Resonance.
  • m of Structure (I) may have an average value of 1.0 or greater, or 1.05 or greater, or 1.10 or greater, or 1.15 or greater, while at the same time, 1.20 or less, or 1.15 or less, or 1.10 or less, or 1.05 or less as measured according to 13 C Nuclear Magnetic Resonance.
  • the m moiety of Structure (I) may also be referred to as glucose repeating unit.
  • the cleaning composition may comprise from 0.01 wt%to 20.0 wt%of the hydrotrope based on a total weight of the cleaning composition.
  • the cleaning composition may comprise 0.01 wt%or greater, or 0.1 wt%or greater, or 0.5 wt%or greater, or 1.0 wt%or greater, or 1.5 wt%or greater, or 2.0 wt%or greater, or 2.5 wt%or greater, or 3.0 wt%or greater, or 3.5 wt%or greater, or 4.0 wt%or greater, or 4.5 wt%or greater, or 5.0 wt%or greater, or 5.5 wt%or greater, or 6.0 wt%or greater, or 6.5 wt%or greater, or 7.0 wt%or greater, or 7.5 wt%or greater, or 8.0 wt%or greater, or 8.5 wt%or greater, or 9.0 wt%or greater, or 9.5 wt%or greater, 10.0 wt
  • the cleaning composition may comprise an alkali salt.
  • the alkali salt may be an alkaline or alkaline earth hydroxide.
  • the alkali salt may be selected from the group consisting of sodium hydroxide (i.e., NaOH) , potassium hydroxide, and/or combinations thereof or with certain amine, such as monoethaonlamine.
  • the cleaning composition may comprise from 0.01 wt. %to 40.00 wt. %of the alkali salt based on a total weight of the cleaning mixture.
  • the cleaning mixture may comprise 0.01 wt. %or greater, or 0.1 wt. %or greater, or 0.50 wt. %or greater, or 1.00 wt. %or greater, or 1.50 wt. %or greater, or 2.00 wt. %or greater, or 2.50 wt. %or greater, or 5.00 wt. %or greater, or 7.50 wt. %or greater, or 10.00 wt. %or greater, or 12.50 wt. %or greater, or 15.00 wt.
  • %or greater or 17.50 wt. %or greater, or 20.00 wt. %or greater, or 22.50 wt. %or greater, or 25.00 wt.%or greater, or 27.50 wt. %or greater, or 30.00 wt. %or greater, or 32.50 wt. %or greater, or 35.00 wt. %or greater, or 37.50 wt. %or greater, while at the same time, 40.00 wt. %or less, or 37.50 wt. %or less, or 35.00 wt. %or less, or 32.50 wt. %or less, or 30.00 wt.
  • %or less or 27.50 wt.%or less, or 25.00 wt. %or less, or 22.50 wt. %or less, or 20.00 wt. %or less, or 17.50 wt. %or less, or 15.00 wt. %or less, or 12.50 wt. %or less, or 10.00 wt. %or less, or 7.50 wt. %or less, or 5.00 wt. %or less, or 2.50 wt. %or less, or 2.00 wt. %or less, or 1.50 wt. %or less, or 1.00 wt. %or less, or 0.50 wt. %or less of the alkali salt based on the total weight of the cleaning composition.
  • the cleaning composition may comprise one or more additives.
  • the cleaning composition may comprise from 0 wt%to 20 wt%of each additive based on the total weight of the cleaning composition.
  • the cleaning composition may comprise 0 wt%or greater, or 1 wt%or greater, or 2 wt%or greater, or 3 wt%or greater, or 4 wt%or greater, or 5 wt%or greater, or 6 wt%or greater, or 7 wt%or greater, or 8 wt%or greater, or 9 wt%or greater, or 10 wt%or greater, or 11 wt%or greater, or 12 wt%or greater, or 13 wt%or greater, or 14 wt%or greater, or 15 wt%or greater, or 16 wt%or greater, or 17 wt%or greater, or 18 wt%or greater, or 19 wt%or greater, while at the same time, 20 wt%or less, or 19 wt%or less
  • the additives may include one or more diluents such as propylene glycol and/or other diluents.
  • the additives may include one or more defoaming agents and/or high molecular weight polyglycols.
  • the additives may include one or more water soluble acrylic copolymers.
  • the additives may include one or more chelating agents such as ethylenediaminetetraacetic ( “EDTA” ) acid, citric acid, potassium citrate, sodium citrate, tetrasodium ethylene-diaminetetraacetate, tetrasodium ethylene-diaminetetraacetate, tetrasodium ethylene-diaminetetraacetate, diammonium ethylene-diaminetetraacetate, tetrasodium ethylene-diaminetetraacetate, tetrasodium ethylene-diaminetetraacetate tetrahydrate, disodium ethylene-diaminetetraacetate tetrahydrate, ethylenediaminetetraacetic acid, disodium ethylene-diaminetetraacetate dihydrate, calcium disodium ethylene-diaminetetraacetate dihydrate, pentasodium diethylenetriaminepentaacetate, pentasodium diethylene-tri
  • 2OG is 2-octyl glucoside having Structure (I) with an m value of 1.0.
  • the 2OG was formed by performing the following steps. First, 2-octanol (36.7 g, 0.282 mol, 1.1 eq. ) and D-glucose penta-acetate (100 g, 0.256 mol, 1 eq. ) were dissolved in 300 mL of dichloromethane (DCM) at 23°C to form a solution. Next, boron trifluoride etherate (40 g, 0.282 mol, 1.1 eq. ) was then added in a dropwise manner over the course of 3 minutes to the solution. The solution was magnetically stirred for 48 hours at 23°C.
  • the crude product was dissolved in mixture solvent (petroleum ether /ethyl acetate 10: 1) and purified by silica gel column (petroleum ether /ethyl acetate 10: 1 by vol. ) to remove the impurity. And then the mixed solvent was distillated out by rotary evaporator under 20 KPa at 30°C to give a yellow solid product (18 g) . The yellow solid product then underwent a de-acetylation process. 10 grams of the yellow solid product was dissolved in 100 mL of methanol. Next, 30 g of anion-exchange resin Amberlite 400 (OH) was added at 23°C in one portion to form a slurry. The slurry was kept magnetic stirring at 23°C overnight.
  • mixture solvent petroleum ether /ethyl acetate 10: 1
  • silica gel column petroleum ether /ethyl acetate 10: 1 by vol.
  • APG is isooctyl Glucoside having a CAS#of 125590-73-0 and a has Structure (II)
  • n 1.4 (i.e., the repeating glucose unit) .
  • APG is commercially available as GREENAPG TM IC-08 from Shanghai Fine Chemical Co., Ltd., Shanghai, CHINA.
  • SURF is a non-ionic branched alcohol alkoxylate surfactant having a cloud point of 35°Cand is commercially available as ECOSURF TM LFE-635 from The Dow Chemical Company, Midland, MI.
  • PG is a 2-octyl polyglucoside having Structure (I) with an m value from greater than 1.5.
  • the PG was formed by performing the following steps. First, 2-octanol (65.1 g, 0.5 mol, 5 eq. ) and D-glucose (18.0 g, 0.1 mol, 1 eq. ) were added to a 100 mL flask. Para-toluene sulfonic acid (0.344 g, 0.002 mol, 0.02 eq. ) was then added in the flask, and the mixture was heated to 110°C in an oil bath with magnetic stirring.
  • NaOH is an aqueous solution of 80 g of sodium hydroxide per liter of water.
  • Hydrotrope Performance Test A water solution of hydrotrope was prepared first at 50 wt.%active concentration. Based on the total amount of each ingredient in the final testing solution (10 mL) : 0.5 g NaOH solid was added into 8.9 g water or 8.4 g water; after its full dissolution, then 0.5 g or 1.0 g hydrotrope water solution (50 wt. %) was added into the 5 wt. %NaOH aq. soln., which targeted to a 2.5 wt. %active or 5 wt. %active concentration of hydrotrope in the final testing solution. Once it was well mixed, 0.1 g SURF was added into the mixture at an active concentration at 1 wt. %.
  • test tube was put into a hot water bath. When the appearance of the testing solution turned hazy, the tube was taken out, then we recorded the temperature where the solution turned from hazy to clear as its cloud point. And, such an operation was repeated three times to get an average cloud point.
  • the test was conducted in accordance with China national standard GB/T 13173-2008 foaming test.
  • a 0.1 wt. %active aqueous solution of hydrotrope was prepared with deionized water.
  • the Ross-Miles test tube was rinsed with deionized water, and previously prepared sample solution (0.1 wt%active aqueous solution) .
  • 50 mL of the sample solution was poured into the test tube. Once no foaming was observed for this first 50 mL of sample solution, 200 mL of sample solution was added via a dropping pipette. The tap of dropping pipette was then opened for the solution to flow down into the test tube. Once the flow of the solution was over, the initial foam height was recorded as the initial height. At the end of 5 min, the foam height was recorded as the final one.
  • Circulating Bubble Foam test A special circulating foaming machine was used. The whole test was carried out at 23°C. About 250 mL of surfactant (0.1%by weight active SURF) aqueous solution was prepared in a beaker. The solution was kept stirring until the SURF was completely dissolved in water, and then it was poured into the glass test bottle. This pouring operation might cause some foam, and the machine was started after the bubbles disappeared. The initial volume reading was 5 mL, representing the volume of the original liquid (the total volume of the foam and liquid was recorded in the test; due to the liquid remaining on the wall in the end of the test, the final volume reading was likely less than 5 mL) . The total test lasted 5 minutes: the machine was on in the first minute and the total volume readings at 15, 30 and 60 seconds were recorded. After turning off the machine for 60 seconds, the total volumes at 75, 90 seconds, 2, 3, 4 and 5 minutes were recorded, respectively.
  • surfactant (0.1%by weight active SURF
  • Table 3 provides the results of the hydrotrope performance test in the 5 wt%NaOH alkaline environment
  • Table 4 provides the results of the Ross-Miles foam test
  • Table 5 provides the results of the circulating foam test at 0.5 wt. %active content.
  • the blank example demonstrates that the SURF (at 1 wt. %) is insoluble in the 5%wt. NaOH water solution without the hydrotrope present.
  • IE1 demonstrates that use of the hydrotrope having Structure (I) (having a glucose repeat unit value of 1.0) provides the greatest increase in cloud point per unit addition of hydrotrope relative to CE1 and CE2.
  • the hydrotrope having Structure (I) is successful in transforming a 1 wt. %nonionic surfactant solution having an initial cloud point at 35°C in a water solution at 23°C is from hazy (i.e., not soluble) to clear with the cloud point of the formulation increasing to 54-57°C with just the addition of 2.5 wt.
  • IE1 is able to achieve the desired target of having an initial foam height of 10 mm or less and 0 mm of foam after 5 minutes.
  • CE1 and CE2 exhibit an initial foam height of 25 mm and 18 mm, respectively.
  • Residual foam for CE1 and CE2 also exist.
  • the hydrotrope of Structure (I) is able to effectively couple the SURF to the alkaline cleaning compositions, produce an initial foam height of 10 mm or less and a foam height less than 0 mm after 5 minutes according to Ross-Miles Foam Testing.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne une composition de nettoyage contenant de l'eau, un tensioactif et un hydrotrope de structure (I), m de structure (I) étant compris entre 1,0 et 1,2 tel que mesuré selon une résonance magnétique nucléaire 13C.
EP22839999.4A 2022-12-05 2022-12-05 Compositions de nettoyage hydrotropiques Pending EP4630524A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2022/136471 WO2024119291A1 (fr) 2022-12-05 2022-12-05 Compositions de nettoyage hydrotropiques

Publications (1)

Publication Number Publication Date
EP4630524A1 true EP4630524A1 (fr) 2025-10-15

Family

ID=84901203

Family Applications (1)

Application Number Title Priority Date Filing Date
EP22839999.4A Pending EP4630524A1 (fr) 2022-12-05 2022-12-05 Compositions de nettoyage hydrotropiques

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Country Link
EP (1) EP4630524A1 (fr)
CN (1) CN120153053A (fr)
WO (1) WO2024119291A1 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3219656A (en) 1963-08-12 1965-11-23 Rohm & Haas Alkylpolyalkoxyalkyl glucosides and process of preparation therefor

Also Published As

Publication number Publication date
CN120153053A (zh) 2025-06-13
WO2024119291A1 (fr) 2024-06-13

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