WO2024115420A1 - Compositions détergentes - Google Patents

Compositions détergentes Download PDF

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Publication number
WO2024115420A1
WO2024115420A1 PCT/EP2023/083236 EP2023083236W WO2024115420A1 WO 2024115420 A1 WO2024115420 A1 WO 2024115420A1 EP 2023083236 W EP2023083236 W EP 2023083236W WO 2024115420 A1 WO2024115420 A1 WO 2024115420A1
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WO
WIPO (PCT)
Prior art keywords
detergent composition
home
composition according
furan
personal care
Prior art date
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PCT/EP2023/083236
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English (en)
Inventor
James Hanley Clark
Craig Jonathon FAIRGRIEVE
Thomas James FARMER
David Stephen Grainger
Kirsten HAWKINS
Sean Philip Nigel Rouse
Original Assignee
Unilever Ip Holdings B.V.
Unilever Global Ip Limited
Conopco, Inc., D/B/A Unilever
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Application filed by Unilever Ip Holdings B.V., Unilever Global Ip Limited, Conopco, Inc., D/B/A Unilever filed Critical Unilever Ip Holdings B.V.
Publication of WO2024115420A1 publication Critical patent/WO2024115420A1/fr

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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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/26—Sulfonic acids or sulfuric acid esters; Salts thereof derived from heterocyclic 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
    • C11D1/83—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
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/12—Soft surfaces, e.g. textile
    • 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
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • 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
    • C11D3/50—Perfumes

Definitions

  • the invention relates to the field of detergent compositions.
  • the compositions are particularly useful for the washing of the items in the home, including dishes, cutlery and other cooking and eating utensils, for in particularly for the laundering of clothes.
  • the compositions of the invention are particularly useful in the field of home care, for example in laundry compositions and hand dish wash compositions.
  • Consumer detergent products particularly those relating to home care purposes, such as laundry and hand dish wash compositions need to address a range of cleaning challenges. There are usually a number of different soil/stain types that need to be addressed by any home care detergent product. Furthermore, these products also need to be able to work under a broad range of conditions (e.g. temperature, water hardness etc..).
  • Typical stains can include fatty and oily stains amongst others.
  • Standard workhorse surfactants typically anionic and nonionics which form the basis of most home care detergent products
  • hydrophobic stains such as fats and oils because they are designed to go to hydrophobic/hydrophilic interfaces.
  • Linear Alkylbenzene Sulphonate (or LAS) is the best current high volume commercial material available.
  • WO2020/229158 discloses furan-based surfactants comprising a beta sulphonate head group, a furan and a C10-20 hydrophobic group which is either attached directly to the furan or by way of a linker.
  • WO2020/229158 discloses multiple linker groups (including ester and amide groups), solely in combination with a furan head group and a beta sulphonate.
  • the invention relates in a first aspect to a detergent composition
  • a detergent composition comprising: from 0.5 to 50 wt.%, preferably from 0.75 to 40 wt.%, more preferably from 1 to 30 wt.% of a furan-based surfactant having the following structure: wherein X is COO or CONH; wherein M is a monovalent cation; preferably Na + , K + , NH 4 + wherein R is a Cs to C carbon chain which is linear or branched, and saturated or unsaturated.
  • the R group is a C12 to C carbon chain.
  • the R group is a saturated alkyl chain.
  • the furan-based surfactant is selected from:
  • the composition additionally comprises a fragrance, preferably from 0.0001 to 5 wt.% of a fragrance.
  • the detergent composition comprises one or more additional surfactants selected from anionic and nonionic surfactants, wherein if present, then the anionic surfactant is present at a level of from 1 to 80 wt.%, preferably from 2 to 50 wt.%, more preferably from 3 to 30 wt.% and is preferably selected from linear alkyl benzenesulphonate, secondary alkane sulphonate, laureth ether sulphate, lauryl sulphate, anionic alkyl polyglycosides, isethionates, alpha olefin sulphonate, internal olefin sulphonate, methyl ester sulphonate, oleyl sulphate, oleyl ether sulphate and rhamnolipids, most preferably selected from linear alkyl benzenesulphonate
  • the composition is a home care detergent composition, more preferably a hand dish wash detergent composition or a laundry detergent composition, most preferably a laundry detergent composition.
  • the home care detergent composition more preferably the laundry detergent composition is in the form of a liquid, solid, powder, pastille, bead or paste, preferably a liquid, solid or powder, more preferably a liquid.
  • the composition is a home care composition
  • the composition additionally comprises from 0.5 to 15 wt.%, more preferably from 0.75 to 15 wt.%, even more preferably from 1 to 12 wt.%, most preferably from 1.5 to 10 wt.% of cleaning boosters selected from antiredeposition polymers, soil release polymers, alkoxylated polycarboxylic acid esters and mixtures thereof, more preferably selected from antiredeposition polymers, and soil release polymers.
  • the antiredeposition polymers are alkoxylated polyamines; and/or wherein the soil release polymer is a polyester soil release polymer.
  • the composition is a home care composition, preferably a laundry composition
  • the composition additionally comprises from 0.05 to 8 wt.%, preferably from 0.1 to 5 wt.%, more preferably from 0.5 to 2 wt.% of a sequestrant, preferably the sequestrant is preferably selected from HEDP, DTPMP, EDTA, MGDA, GLDA or citric acid.
  • the invention relates to the use of a furan-based surfactant as defined in the first aspect in a laundry process to improve soil removal from fabrics.
  • the detergent composition comprises from 0.5 to 50 wt.%, preferably from 0.75 to 40 wt.%, more preferably from 1 to 30 wt.%of a furan-based surfactant having the following structure: wherein X is COO or CONH; wherein M is a monovalent cation; preferably Na + , K + , NH 4 + wherein R is a Cs to C carbon chain which is linear or branched, and saturated or unsaturated.
  • the furan-based surfactant has the following structure: wherein X is COO or CONH; wherein M is a monovalent cation; preferably Na + , K + , NH 4 + wherein R is a Cs to C carbon chain which is linear or branched, and saturated or unsaturated.
  • R group is a C12 to C carbon chain.
  • the R group is a saturated alkyl chain.
  • Preferred furan-based surfactants are selected from:
  • the R group can be linear or branched, preferably it is linear.
  • While the carbon chain, R, of the furan-based surfactant may be linear or branched, preferably the carbon chain of the furan-based surfactant is linear.
  • the linker group ‘X’ is COO or CONH giving an ester or an amide linkage between the furan group and the carbon chain R. Most preferably X is COO to give an ester linkage.
  • M is a monovalent cation; preferably Na + , K + , NF , more preferably Na + .
  • the furan ring creates a naturally occurring aromatic structure in the surfactant headgroup.
  • the furan ring group can be achieved through dehydration of sugars from biomass.
  • the furan-based surfactants can be made by any suitable process, particularly suitable processes are exemplified in the examples.
  • the home or personal care detergent composition is suitable for uses in home care or in personal care, for example hand dish wash or laundry for home care, or washing the hands, body, face or hair for personal care.
  • the composition is a home care detergent composition, preferably a hand dish wash detergent composition or a laundry detergent composition, more preferably a laundry detergent composition.
  • the home care detergent composition preferably a laundry detergent composition
  • the home care detergent composition is in the form of a liquid, solid, powder, pastille, bead or paste, more preferably a liquid, solid or powder, more preferably a liquid. It may be preferred that the composition is a liquid detergent composition, preferably a nonaqueous liquid detergent composition.
  • the home or personal care detergent composition as herein described additionally comprises a fragrance, preferably from 0.0001 to 5 wt.% of a fragrance.
  • a fragrance preferably from 0.0001 to 5 wt.% of a fragrance.
  • fragrance and perfume are used interchangeably.
  • the composition preferably comprises a perfume.
  • perfumes are provided in the CTFA (Cosmetic, Toiletry and Fragrance Association) 1992 International Buyers Guide, published by CFTA Publications and OPD 1993 Chemicals Buyers Directory 80th Annual Edition, published by Schnell Publishing Co.
  • the perfume comprises at least one note (compound) from: alpha-isomethyl ionone, benzyl salicylate; citronellol; coumarin; hexyl cinnamal; linalool; pentanoic acid, 2-methyl-, ethyl ester; octanal; benzyl acetate; 1 ,6-octadien-3-ol, 3,7-dimethyl-, 3-acetate; cyclohexanol, 2-(1 , 1- dimethylethyl)-, 1 -acetate; delta-damascone; beta-ionone; verdyl acetate; dodecanal; hexyl cinnamic aldehyde; cyclopentadecanolide; benzeneacetic acid, 2-phenylethyl ester; amyl salicylate; beta-caryophyllene; ethyl undecylenate;
  • Useful components of the perfume include materials of both natural and synthetic origin. They include single compounds and mixtures. Specific examples of such components may be found in the current literature, e.g., in Fenaroli's Handbook of Flavour Ingredients, 1975, CRC Press; Synthetic Food Adjuncts, 1947 by M. B. Jacobs, edited by Van Nostrand; or Perfume and Flavour Chemicals by S. Arctander 1969, Montclair, N.J. (USA).
  • the home or personal care detergent composition may additionally comprise one or more additional surfactants selected from anionic and nonionic surfactants. If present, then the anionic surfactant is present at a level of from 1 to 80 wt.%, preferably from 2 to 50 wt.%, more preferably from 3 to 30 wt.% and is preferably selected from linear alkyl benzenesulphonate, secondary alkane sulphonate, laureth ether sulphate, lauryl sulphate, anionic alkyl polyglycosides, isethionates, alpha olefin sulphonate, internal olefin sulphonate, methyl ester sulphonate, oleyl sulphate, oleyl ether sulphate and rhamnolipids, most preferably selected from linear alkyl benzenesulphonate, secondary alkane sulphonate, laureth ether sulphate, lauryl sulphate
  • the nonionic surfactant is present at a level of from 1 to 80 wt.%, preferably from 2 to 50 wt.%, more preferably from 3 to 30 wt.% and is preferably selected from an alcohol ethoxylate, an alcohol propoxylate, a methyl ester ethoxylate, and an alkyl poly glycoside.
  • Most preferred nonionic surfactants are preferably selected from alcohol ethoxylates having from C12-C15 with a mole average of from 5 to 9 ethoxylates and/or alcohol ethoxylates having from C16-C18 with a mole average of from 5 to 14 ethoxylates.
  • the composition additionally comprises an enzyme, preferably comprising from 0.05 to 5 wt.%, more preferably from 0.1 to 4 wt.%, more preferably from 0.5 to 3 wt.% of an enzyme, wherein the enzyme is preferably selected from one or more of a protease, amylase, mannanase, cellulase, lipase, pectate lyase, laccase, phosphodiesterase and mixtures thereof.
  • an enzyme preferably comprising from 0.05 to 5 wt.%, more preferably from 0.1 to 4 wt.%, more preferably from 0.5 to 3 wt.% of an enzyme, wherein the enzyme is preferably selected from one or more of a protease, amylase, mannanase, cellulase, lipase, pectate lyase, laccase, phosphodiesterase and mixtures thereof.
  • the composition additionally comprises from 0.5 to 15 wt.%, more preferably from 0.75 to 15 wt.%, even more preferably from 1 to 12 wt.%, most preferably from 1.5 to 10 wt.% of cleaning boosters selected from antiredeposition polymers; soil release polymers; alkoxylated polycarboxylic acid esters, and mixtures thereof. More preferably selected from antiredeposition polymers, and/or soil release polymers.
  • Preferred antiredeposition polymers include alkoxylated polyamines.
  • a preferred alkoxylated polyamine comprises an alkoxylated polyethylenimine, and/or alkoxylated polypropylenimine.
  • the polyamine may be linear or branched. It may be branched to the extent that it is a dendrimer.
  • the alkoxylation may typically be ethoxylation or propoxylation, or a mixture of both. Where a nitrogen atom is alkoxylated, a preferred average degree of alkoxylation is from 10 to 30, preferably from 15 to 25.
  • a preferred material is ethoxylated polyethyleneimine, with an average degree of ethoxylation being from 10 to 30 preferably from 15 to 25, where a nitrogen atom is ethoxylated.
  • the soil release polymer is a polyester soil release polymer.
  • Preferred soil release polymers include those described in WO 2014/029479 and WO 2016/005338.
  • polyester based soil release polymer is a polyester according to the following formula (I) wherein
  • R 1 and R 2 independently of one another are X-(OC2H4)n-(OC3H6)m wherein X is C1.4 alkyl and preferably methyl, the -(OC2H4) groups and the -(OCsHe) groups are arranged blockwise and the block consisting of the -(OCsHe) groups is bound to a COO group or are HO-(C 3 H6), and preferably are independently of one another X-(OC2H4)n- (OC 3 H 6 )m, n is based on a molar average number of from 12 to 120 and preferably of from 40 to 50, m is based on a molar average number of from 1 to 10 and preferably of from 1 to 7, and a is based on a molar average number of from 4 to 9.
  • the polyester provided as an active blend comprising:
  • R 1 and R 2 independently of one another are X-(OC2H4)n-(OC3H6)m wherein X is C1.4 alkyl and preferably methyl, the -(OC2H4) groups and the -(OCsHe) groups are arranged blockwise and the block consisting of the -(OCsHe) groups is bound to a COO group or are HO ⁇ CsHe), and preferably are independently of one another X-(OC2H4)n- (OC 3 H 6 )m, n is based on a molar average number of from 12 to 120 and preferably of from 40 to 50, m is based on a molar average number of from 1 to 10 and preferably of from 1 to 7, and a is based on a molar average number of from 4 to 9 and
  • Alkoxylated polycarboxylic acid esters are obtainable by first reacting an aromatic polycarboxylic acid containing at least three carboxylic acid units or anhydrides derived therefrom, preferably an aromatic polycarboxylic acid containing three or four carboxylic acid units or anhydrides derived therefrom, more preferably an aromatic polycarboxylic acid containing three carboxylic acid units or anhydrides derived therefrom, even more preferably trimellitic acid or trimellitic acid anhydride, most preferably trimellitic acid anhydride, with an alcohol alkoxylate and in a second step reacting the resulting product with an alcohol or a mixture of alcohols, preferably with C16/C18 alcohol.
  • the composition additionally comprises from 0.05 to 8 wt.%, preferably from 0.1 to 5 wt.%, more preferably from 0.5 to 2 wt.% of a sequestrant, preferably the sequestrant is preferably selected from HEDP, DTPMP, EDTA, MGDA, GLDA or citric acid.
  • the formulation may contain further ingredients.
  • the detergent formulation in the form of a non-liquid, preferably powder preferably comprises a builder or a complexing agent. This may be present at levels of from 5 to 75 wt.%, preferably from 8 to 65 wt.%, more preferably from 10 to 60 wt.% of the detergent composition.
  • Such materials may include: calcium sequestrant materials; precipitating materials; calcium ionexchange materials; and mixtures thereof.
  • Preferred examples of such materials include carbonates, layered silicates, polycarboxylates (e.g. EDTA, NTA), citrates (e.g. trisodium citrate), silicates (e.g. sodium silicate) and zeolites.
  • polycarboxylates e.g. EDTA, NTA
  • citrates e.g. trisodium citrate
  • silicates e.g. sodium silicate
  • zeolites zeolites.
  • Preferred builders or complexing agents are carbonates, for example sodium carbonate.
  • the detergent formulation in the form of a non-liquid, preferably powder preferably comprises less than 20 wt.%, more preferably less than 15 wt.%, most preferably less than 10 wt.% of zeolite (an aluminosilicate material).
  • the detergent formulation comprises less than 1 wt.% of phosphate.
  • the detergent formulation in the form of a non-liquid, preferably powder can preferably be not built i.e., contain less than 1 wt.% of builder.
  • the detergent composition is an aqueous liquid laundry detergent it is preferred that mono propylene glycol or glycerol is present at a level from 1 to 30 wt.%, most preferably 2 to 18 wt.%.
  • the composition preferably comprises a fluorescent agent (optical brightener).
  • Fluorescent agents are well known and many such fluorescent agents are available commercially. Usually, these fluorescent agents are supplied and used in the form of their alkali metal salts, for example, the sodium salts.
  • the total amount of the fluorescent agent or agents used in the composition is generally from 0.0001 to 0.5 wt.%, preferably 0.005 to 2 wt.%, more preferably 0.01 to 0.1 wt.%.
  • Preferred classes of fluorescer are: Di-styryl biphenyl compounds, e.g. Tinopal (Trade Mark) CBS-X, Di-amine stilbene di-sulphonic acid compounds, e.g. Tinopal DMS pure Xtra and Blankophor (Trade Mark) HRH, and Pyrazoline compounds, e.g. Blankophor SN.
  • Di-styryl biphenyl compounds e.g. Tinopal (Trade Mark) CBS-X
  • Di-amine stilbene di-sulphonic acid compounds e.g. Tinopal DMS pure Xtra and Blankophor (Trade Mark) HRH
  • Pyrazoline compounds e.g. Blankophor SN.
  • Preferred fluorescers are fluorescers with CAS-No 3426-43-5; CAS-No 35632-99-6; CAS-No 24565-13-7; CAS-No 12224-16-7; CAS-No 13863-31-5; CAS-No 4193-55-9; CAS-No 16090- 02-1; CAS-No 133-66-4; CAS-No 68444-86-0; CAS-No 27344-41-8.
  • fluorescers are: sodium 2 (4-styryl-3-sulfophenyl)-2H-napthol[1 ,2-d]triazole, disodium 4,4'-bis ⁇ [(4-anilino-6-(N methyl-N-2 hydroxyethyl) amino 1 ,3,5-triazin-2- yl)]amino ⁇ stilbene-2-2' disulphonate, disodium 4,4'-bis ⁇ [(4-anilino-6-morpholino-1 , 3, 5-triazi n-2- yl)]amino ⁇ stilbene-2-2' disulphonate, and disodium 4,4'-bis(2-sulphostyryl)biphenyl.
  • shading dye present in the formulation, especially if the composition is a laundry composition.
  • Dyes are described in Color Chemistry Synthesis, Properties and Applications of Organic Dyes and Pigments, (H Zollinger, Wiley VCH, Zurich, 2003) and, Industrial Dyes Chemistry, Properties Applications. (K Hunger (ed), Wiley-VCH Weinheim 2003).
  • Dyes for use in laundry detergents preferably have an extinction coefficient at the maximum absorption in the visible range (400 to 700nm) of greater than 5000 L mol -1 cm -1 , preferably greater than 10000 L mol -1 cm -1 .
  • Preferred dye chromophores are azo, azine, anthraquinone, phthalocyanine and triphenylmethane.
  • Azo, anthraquinone, phthalocyanine and triphenylmethane dyes preferably carry a net anionic charged or are uncharged.
  • Azine dyes preferably carry a net anionic or cationic charge.
  • Shading dyes deposit to fabric during the wash or rinse step of the washing process providing a visible hue to the fabric.
  • the dye gives a blue or violet colour to a white cloth with a hue angle of 240 to 345, more preferably 260 to 320, most preferably 270 to 300.
  • the white cloth used in this test is bleached nonmercerised woven cotton sheeting.
  • a mixture of shading dyes may be used.
  • the shading dye is preferably present in the composition in range from 0.0001 to 0.1 wt %. Depending upon the nature of the shading dye there are preferred ranges depending upon the efficacy of the shading dye which is dependent on class and particular efficacy within any particular class. As stated above the shading dye is preferably a blue or violet shading dye.
  • the composition may comprise one or more further polymers.
  • suitable polymers are carboxymethylcellulose, poly (ethylene glycol), poly(vinyl alcohol), polycarboxylates such as polyacrylates, maleic/acrylic acid copolymers and lauryl methacrylate/acrylic acid copolymers.
  • alkyl groups are sufficiently long to form branched or cyclic chains, the alkyl groups encompass branched, cyclic and linear alkyl chains.
  • the alkyl groups are preferably linear or branched, most preferably linear.
  • the detergent compositions optionally include one or more laundry adjunct ingredients.
  • an anti-oxidant may be present in the formulation.
  • amalgamate ingredient includes: perfumes, dispersing agents, stabilizers, pH control agents, metal ion control agents, colorants, brighteners, dyes, odour control agent, properfumes, cyclodextrin, solvents, soil release polymers, preservatives, antimicrobial agents, chlorine scavengers, anti-shrinkage agents, fabric crisping agents, spotting agents, antioxidants, anti-corrosion agents, bodying agents, drape and form control agents, smoothness agents, static control agents, wrinkle control agents, sanitization agents, disinfecting agents, germ control agents, mould control agents, mildew control agents, antiviral agents, antimicrobials, drying agents, stain resistance agents, soil release agents, malodour control agents, fabric refreshing agents, chlorine bleach odour control agents, dye fixatives, dye transfer inhibitors, shading dyes, colour maintenance agents, colour restoration, rejuvenation agents, anti-fading agents, whiteness enhancers, anti-abrasion agents, wear resistance agents
  • N-(2-hexyldecyl)-5-methylfuran-2-carboxamide 5-methyl-2-furoic acid (1 g, 7.93 mmol) was dissolved in dichloromethane (30mL) and stirred at 0 °C for 5 minutes. Then EDC «HCI (2.63 g, 13.80 mmol) and DMAP (0.96 g, 7.93 mmol) were added the solution was stirred for ca. 30 minutes before addition of 2-hexadecan-1 -amine (2.33 mL, 7.93 mmol). The mixture was stirred for 2 hours at 0 °C followed by a 12 hour stir at room temperature.
  • Tetradecylamine (4.82 g, 0.0226 mol) and methyl 5-methylfuran-2-furoate (2.80 g, 0.02 mol) were heated for 30 minutes at 75°C with stirring under a nitrogen headspace purge exhausting via a condenser configured for distillation.
  • Sodium methoxide (0.05 g, 5 mol %) was added and heating was continued at 75°C for 6 h before cooling to ambient.
  • the crude product was dissolved in a mixture of ethyl acetate and washed with 2.5 M HCI (3 x 100 ml) and brine (4 x 100 ml).
  • the organic layer was separated, and the solvent evaporated to yield the crude product (6.50 g), which tic indicated to contain tetradecylamine hydrochloride by-product.
  • the crude product was purified by dry flash chromatography (eluent ethyl acetate:methanol, 10:1) to yield N-tetradecyl- 5-methyl-2-furamide as a pale cream wax (4.43 g, 69%).
  • Tetradecanol (4.29 g, 0.02 mol) and methyl 5-methylfuran-2-furoate (2.80 g, 0.02 mol) were heated for 30 minutes at 105°C with stirring under a nitrogen headspace purge exhausting via a condenser configured for distillation.
  • the mixture was then cooled to 90°C and stirred for 1 h before cooling to 60°C and adding sodium methoxide (0.05 g, 5 mol %).
  • the reaction was then heated at 80°C for 4 h before cooling to ambient. Further methyl 5-methylfuran-2-carboxylate (0.16 g, 0.0011 mol) was charged, and reaction was continued at 80°C under nitrogen for 3 h.
  • Hexadecanol (4.85 g, 0.02 mol) was heated for 30 minutes at 100°C with stirring under a nitrogen headspace purge exhausting via a condenser configured for distillation. After cooling to 70°C, methyl 5-methylfuran-2-furoate (2.80 g, 0.02 mol) was added, and the mixture stirred for 30 minutes. Sodium methoxide (0.05 g, 5 mol %) was charged and the temperature increased to 80°C for 4.5 h. The reaction was cooled to 70°C and lactic acid (0.09 g) added. The crude product was dissolved in ethyl acetate and the precipitated catalyst residue was filtered off. The solvent was evaporated to yield hexadecyl-5-methyl-2-furoate as a pale brown wax (6.69 g, 95%).
  • N-dodecyl-4-methylsulfonate-5-methyl-2-furamide N-dodecyl-5-methyl-2-furamide (1.47 g, 0.005 mol), DMF-SO3 (0.77 g, 0.005 mol) and anhydrous acetonitrile (15 ml) were heated under reflux at 85°C for 26 h. The reaction was cooled to room temperature and neutralised to pH 7 by addition of Na 2 CO3 (0.32 g, 0.003 mol) in water (10 ml). After filtration (to remove humins) the clear filtrate was carefully evaporated to dryness by azeotroping with fresh acetonitrile to prevent excessive foaming.
  • the resultant amber foam was further dried in vacuo over P2O5.
  • the dried foam (2.12 g) was triturated with hot heptane; the resulting powdery solid filtered off and the heptane evaporated to yield unreacted starting material (0.10 g).
  • the powdery solid (1.93 g) was triturated with hot acetonitrile; the residual powdery solid filtered off and the acetonitrile evaporated to yield further starting material (0.03 g).
  • the powdery solid (1.86 g) was triturated with hot methanol and the resulting insoluble inorganic solids filtered off (0.04 g). The methanol solution was evaporated to dryness yielding the desired product as a cream powder (1.49 g, 75%).
  • the resultant amber gum (14.87 g) was triturated with heptane but the resulting semi-solid could not be filtered.
  • the contaminated filter papers and filter funnel were washed through with methanol and the solvent evaporated to yield an amber gum (2.63 g, 85:15 mixture of product: starting material).
  • the semi-solid that had been collected and the heptane were recombined and water (100 ml) and NaCI (5 g) added, forming a clear heptane layer (A), an emulsified interfacial layer (B), and a hazy aqueous layer (C).
  • the clear heptane layer (A) was evaporated to dryness yielding an oil (0.59 g, starting material) and the interfacial layer (B) was separated by addition of further NaCI, with evaporation of the heptane yielding an amber gum (1.81 g, 60:40 mixture of product: starting material).
  • the hazy aqueous layer (C) was separated off and extracted with ethyl acetate (150 ml); evaporation of the solvent gave an amber gum (5.65 g).
  • the gum was washed with hot heptane, with successive solvent additions decanted off and combined. Removal of the heptane gave 0.13 g of starting material.
  • the residue was dried to remove traces of heptane, yielding the target sulfonated product as a brittle, slightly sticky pale orange foam (4.52 g, 38%).
  • the resultant amber solid (1.80 g) was triturated with hot heptane; the resulting powdery solid filtered off and the heptane evaporated to yield unreacted starting material (0.14 g).
  • the powdery solid (1.51 g) was triturated with hot methanol and the insoluble inorganic solids filtered off (0.05 g, sodium sulfate and sodium carbonate). The clear filtrate was evaporated to dryness yielding the desired product as a cream powder (1.28 g, 60%).
  • Tetradecyl 5-methylfuran-2-carboxylate (1.61 g, 0.005 mol), DMF-SO3 (0.77 g, 0.005 mol) and anhydrous acetonitrile (15 ml) were heated under reflux at 85°C for 26 h.
  • the reaction was cooled to room temperature and neutralised to pH 7 by addition of Na 2 CO3 (0.37 g, 0.0035 mol) in water (20 ml). After stirring for 1 h the reaction was filtered to separate off a precipitate (0.35 g, unreacted starting material). The clear filtrate was carefully evaporated to dryness by azeotroping with fresh acetonitrile to prevent excessive foaming.
  • the resultant amber foam (1.73 g) was triturated with hot heptane, the resulting powdery solid filtered off and the heptane evaporated to yield further unreacted starting material (0.26 g).
  • the powdery solid (1.40 g) was triturated with methanol and the insoluble inorganic solids filtered off (0.23 g, sodium sulfate). The clear filtrate was evaporated to dryness yielding the desired product as a pale orange powder (1.07 g, 50%).
  • furan-based surfactants such as: can be made in a similar fashion to the materials described above.
  • 5-methyl-2- furoic acid is dissolved in dichloromethane (30mL) and stirred at 0 °C for 5 minutes.
  • EDC «HCI and DMAP are added and the solution was stirred for ca. 30 minutes before addition of the required amount of 2-octyldecanol, hexadecyl amine or dodecanol.
  • the mixture then stirred for 2 hours at 0 °C followed by a 12 hour stir at room temperature.
  • the reaction mixture is then washed with 2 M hydrochloric acid solution (20 mL), water, 1 M NaOH (20 mL) and brine (20 mL).
  • the organic solvent is dried over magnesium sulfate.
  • the organic solvent is removed in vacuo to yield the product.
  • the product(s) are then sulfated as described above to yield the furan-based surfactants.
  • the comparative control will be a commercial grade of LAS.
  • Neodol 25-7 Ex Shell: a C12-15 alcohol ethoxylate nonionic surfactant with an average 7EO groups
  • water 24FH water hardness
  • furan-based surfactants of the invention perform extremely well and compare well to the high performing benchmark anionic surfactant LAS.
  • Knitted cotton fabric that had been stained with Yellow Curry, Tomato & Sunflower Oil, Economy Chocolate Ice Cream and Chilli Con Carne
  • Knitted polyester fabric that had been stained with Lard & Violet Dye, Red Pepper Oil and Cooking Oil & Violet Dye
  • the fabrics were washed for 30 min @ 100 rpm at 30°C (i.e. at a temperature just above ambient so it could be controlled). 50 stainless steel balls were added for agitation.
  • Furans 1 and 5 (as according to example 2) were synthesized and compared with surfactants made according to WO2020/229158.
  • Furans 2 and 5 and comparative samples B, C and D were gently stirred for 1 hour into demineralised water at room temperature at a concentration of 50g/l. The samples were then left to stand and assessed visually after 5 mins. For some of the samples a non-ionic surfactant with a C12-15 alkyl chain and an average of 7EO groups (Neodol 25-7, ex: Shell) was also added (at a 3:1 weight ratio of test surfactants to non-ionic surfactant). This was done with the aim of further improving surfactant solubility.
  • the furan surfactants are easily incorporated in the following exemplar detergent compositions.

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Abstract

L'invention concerne une composition détergente d'entretien de la maison ou de soins personnels, comprenant : de 0,5 à 50 % en poids d'un tensioactif à base de furane ayant la structure suivante : (I) dans laquelle X représente une fraction de liaison ; M représente un cation monovalent ; R représente une chaîne carbonée en C8 à C18 qui est linéaire ou ramifiée et saturée ou insaturée ; et R1 représente une chaîne alkyle en C 1 à C12 ; l'invention concerne en outre l'utilisation dudit tensioactif à base de furane dans un procédé de blanchissage pour améliorer l'élimination de salissures de tissus.
PCT/EP2023/083236 2022-11-28 2023-11-27 Compositions détergentes WO2024115420A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014029479A1 (fr) 2012-08-18 2014-02-27 Clariant International Ltd Utilisation de polyesters dans des produits de lavage et de nettoyage
WO2016005338A1 (fr) 2014-07-09 2016-01-14 Clariant International Ltd Compositions stables au stockage contenant des polymères détachants
WO2020229158A1 (fr) 2019-05-10 2020-11-19 Unilever Plc Composé et composition détergente
US20220204467A1 (en) * 2020-05-04 2022-06-30 Sironix Renewables, Inc. Furan surfactant compositions and methods

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014029479A1 (fr) 2012-08-18 2014-02-27 Clariant International Ltd Utilisation de polyesters dans des produits de lavage et de nettoyage
WO2016005338A1 (fr) 2014-07-09 2016-01-14 Clariant International Ltd Compositions stables au stockage contenant des polymères détachants
WO2020229158A1 (fr) 2019-05-10 2020-11-19 Unilever Plc Composé et composition détergente
US20220204467A1 (en) * 2020-05-04 2022-06-30 Sironix Renewables, Inc. Furan surfactant compositions and methods

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"Chemicals Buyers Directory", 1993, SCHNELL PUBLISHING CO
"International Buyers Guide", 1992, CFTA PUBLICATIONS, article "Cosmetic, Toiletry and Fragrance Association"
DAE SUNG PARK ET AL: "Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans", ACS CENTRAL SCIENCE, vol. 2, no. 11, 19 October 2016 (2016-10-19), pages 820 - 824, XP055634356, ISSN: 2374-7943, DOI: 10.1021/acscentsci.6b00208 *
H ZOLLINGER: "Color Chemistry Synthesis, Properties and Applications of Organic Dyes and Pigments", 2003, WILEY-VCH

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