Buddy and Home Care Products
A novel surfactant of formula I, with specific aryl and aliphatic groups, addresses the need for diverse surfactants in fabric care by providing improved biodegradability and toxicity profiles, enhancing product performance and sustainability.
Patent Information
- Application Number
- JP2024575767
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2022-07-01
- Filing Date
- 2023-04-21
- Publication Date
- 2025-07-03
- Estimated Expiration
- 2043-04-21
AI Technical Summary
Existing fabric care products require different surfactants for varying benefits on different surfaces, necessitating the development of new surfactants with desired properties.
The use of a novel surfactant of formula I, characterized by specific aryl and aliphatic groups, which provides good toxicity and environmental profiles, including improved biodegradability compared to arylalkyl ketone sulfonates.
The surfactant of formula I offers enhanced biodegradability and toxicity profiles, effectively addressing the need for versatile surfactants in fabric and home care products, improving their performance and environmental sustainability.
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Figure 2025520755000001_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to fabrics and home care products containing a surfactant of formula I.
Background Art
[0002] Fabric care products often utilize surfactants. Different surfactants may be required to obtain different benefits or even the same benefits on different surfaces. This is suitable for the development of new surfactants that can have the desired properties. Therefore, new surfactants are needed.
Summary of the Invention
Means for Solving the Problems
[0003] This specification includes fabrics and home care products containing a surfactant of formula I.
[0004]
Chemical Formula
[0005] This iteration and other iterations will be more fully described in the remainder of the following description.
Mode for Carrying Out the Invention
[0006] This application relates to a fabric care product containing a novel surfactant of formula I. Formula I is
[0007]
Chemical Formula
[0008] The compounds of formula I have been found to provide good toxicity and environmental profiles. Furthermore, the compounds of the invention exhibit a good biodegradability profile, which has been found to be improved compared to the corresponding arylalkyl ketone sulfonates of general formula VI, Ar-C(=O)-CH(SO3X)-R3. Arylalkyl ketone sulfonates are known, for example, from International Publication No. WO 2018 / 229285 (A1).
[0009] In the context of the present invention, the "aryl group" (Ar) means an aromatic group, i.e., a cyclic conjugated unsaturated hydrocarbon ring having a number of delocalized π electrons in accordance with Hückel's rule. Polycyclic aromatic groups are also included, and the cyclic aromatic rings can be fused or linked by C-C bonds. Heteroaromatic groups, i.e., cyclic or polycyclic conjugated unsaturated rings containing one or more heteroatoms having a number of delocalized π electrons in accordance with Hückel's rule (e.g., furan, pyridine, pyrrole as described in more detail below) are also included. The aryl group can be optionally further substituted by one or more functional groups.
[0010] An example of an aromatic ring as the aryl group Ar is phenyl, which can be optionally further substituted by one or more functional groups. Ar may represent a substituted phenyl group of the following formula.
[0011]
Chemical formula
[0012] Examples of heteroaromatic rings as the aryl group Ar include pyridyl, furanyl, pyrrolyl, thiophenyl, pyrazolyl, imidazolyl, benzimidazolyl, indolyl, quinolinyl, isoquinolinyl, purinyl, pyrimidinyl, thiazolyl, pyrazinyl, pyridazinyl, oxazolyl, and triazolyl, which may be further substituted by one or more functional groups.
[0013] For example, Ar may represent an optionally substituted 2-pyridyl, 3-pyridyl or 4-pyridyl group of the formula.
[0014] [Chemistry] In the formula, X1, X2, X3, and X4 may be the same or different and have the same meaning as described above.
[0015] Ar may also represent an optionally substituted furan-2-yl group or furan-3-yl group of the formula.
[0016] [Chemistry] In the formula, X1, X2, and X3 may be the same or different and have the same meaning as described above.
[0017] Ar may also represent an optionally substituted 1H-pyrrol-2-yl or 1H-pyrrol-3-yl group.
[0018] [Chemistry] In the formula, X1, X2, X3, and X4 may be the same or different and have the same meaning as described above.
[0019] Ar may also represent an optionally substituted thiophen-2-yl group or thiophen-3-yl group.
[0020] [Chemistry]
[0021] In some embodiments, the substituents X i and X i+1 together form an optionally substituted cyclic moiety, which is an aromatic group, a heteroaromatic group, or a non-aromatic group.
[0022] In a preferred embodiment of the present invention, the aryl group Ar is a phenyl group.
[0023] "R3" in the context of the present invention generally represents a C6-C 16 aliphatic group, preferably a C 10 -C 16 aliphatic group.
[0024] The aliphatic group R3 may not contain double bonds and triple bonds. Alternatively, the aliphatic group R3 may also contain at least one C-C double bond and / or at least one C-C triple bond.
[0025] The aliphatic group R3 may be linear or branched, and is preferably a linear alkyl group.
[0026] The aliphatic group R3 is preferably selected from an alkyl group, an alkenyl group, an alkadienyl group, and an alkatrienyl group. More preferably, it is selected from an alkyl group, an alkenyl group, and an alkatrienyl group.
[0027] Even more preferably, the aliphatic group R3 is selected from alkyl and alkenyl groups, generally C6-C 16 alkyl and C6-C 16 alkenyl groups, preferably C 10 -C 16 alkyl and C 10 -C 16 alkenyl groups.
[0028] Even still more preferably, R3 represents a C6-C 16 alkyl group, which can be a branched or linear alkyl group, preferably a linear alkyl group.
[0029] The cation X in the SO3X group of the compound of the present invention is selected from an alkali metal, an alkaline earth metal, and ammonium.
[0030] Suitable alkali metals as group X for use in the present invention include lithium (Li), sodium (Na), potassium (K), rubidium (Rb), and cesium (Cs), with lithium, sodium, and potassium being preferred alkali metals and sodium being a particularly preferred alkali metal.
[0031] Suitable alkaline earth metals as group X for use in the present invention include beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), and barium (Ba), with magnesium and calcium being preferred alkaline earth metals.
[0032] Ammonium suitable as group X for use in the present invention has the general formula R’R’’R’’’R’’’’N, where R’, R’’, R’’’, and R’’’’ are independently selected from hydrocarbyl groups that may be optionally substituted and / or interrupted by one or more heteroatom-containing groups. The term “hydrocarbyl” as used herein includes aryl groups and aliphatic groups, which may be optionally substituted and / or interrupted by one or more heteroatom-containing groups. Such heteroatom-containing groups include nitrogen-containing groups such as primary, secondary, and tertiary amines, as well as oxygen-containing groups such as hydroxyl groups and ether groups. Preferred ammonium suitable as group X for use in the present invention includes, for example, NH4, N(CH3)4, triethanolammonium.
[0033] Preferred compounds of formula I are defined as follows.
[0034] R1 is OSO3X, where X is defined as above and in the claims, R2 is H, and R3 is a linear alkyl group C6~C 16 and R1 is OH, R2 is SO3X, where X is as defined above and in the claims, and R3 is a linear alkyl group C6~C 16 and R1 is H, R2 is SO3X, where X is as defined above and in the claims, and R3 is a linear alkyl group C6 - C 16 is.
[0035] More preferred compounds of formula I are defined as follows.
[0036] Ar is phenyl, R1 is OSO3X, where X is sodium, R2 is H, and R3 is a linear alkyl group C6 - C 16 is, Ar is phenyl, R1 is OH, R2 is SO3X, where X is sodium, and R3 is a linear alkyl group C6 - C 16 is, Ar is phenyl, R1 is H, R2 is SO3X, where X is sodium, and R3 is a linear alkyl group C6 - C 16 is.
[0037] The biodegradability of the compounds of the present invention can be determined according to well-known standard protocols that follow OECD guidelines such as the OECD 301F protocol. An alternative protocol developed by the inventors for the determination of the biodegradability of the compounds of the present invention disclosed herein is described in the Examples section.
[0038] Fabrics and home care products Fabric and home care products may contain a surfactant of Formula I. The fabric and home care products may contain from about 0.1 wt% to about 99 wt% of the surfactant of Formula I based on the weight of the product. Further, the fabric and home care products may contain from about 1 wt% to about 99 wt%, from about 2 wt% to about 95 wt%, from about 3 wt% to about 92 wt%, from about 4 wt% to about 90 wt%, from about 5 wt% to about 85 wt%, from about 5 wt% to about 80 wt%, from about 5 wt% to about 75 wt%, from about 5 wt% to about 70 wt%, from about 5 wt% to about 70 wt%, from about 5 wt% to about 65 wt%, from about 5 wt% to about 60 wt%, from about 5 wt% to about 55 wt%, from about 5 wt% to about 50 wt%, from about 5 wt% to about 45 wt%, from about 5 wt% to about 15 wt%, from about 5 wt% to about 25 wt%, from about 15 wt% to about 45 wt%, or from about 25 wt% to about 60 wt% of the surfactant of Formula I based on the weight of the fabric and home care products.
[0039] Fabric and home care products may include, for example, hard surface cleaners, hard surface treatment agents, laundry detergents, fabric softeners, dishwashing detergents, fabric conditioners, laundry additives, rinse additives, or combinations thereof. Fabric care products may include compositions and formulations designed to treat fabrics. Such compositions include laundry washing compositions and detergents, fabric softening compositions, fabric strengthening compositions, fabric deodorizing compositions, pre-wash detergents, pre-wash treatment agents, laundry additives, spray products, dry cleaning agents or compositions, laundry rinse additives, cleaning additives, post-rinse fabric treatment agents, ironing aids, unit dose formulations, delayed delivery formulations, detergents contained on or in porous substrates or nonwoven sheets, and other suitable forms that may be apparent to those skilled in the art in view of the teachings herein, but are not limited thereto. Such compositions can be used as pre-wash treatment agents, post-wash treatment agents, or added during the rinse or wash cycle of a laundry operation.
[0040] Fabric and home care product compositions may be in the form of liquid compositions, granular compositions, hydrocolloids, single-compartment pouches, multi-compartment pouches, soluble sheets, troches or beads, fibrous articles, tablets, sticks, bars, flakes, foams / mousses, nonwoven sheets, or mixtures thereof.
[0041] The fabric and home care products may be in liquid form. The liquid composition may contain from about 1, 5, 10, 20, 30 weight % of the composition, or from about 40 weight %, or from about 50 weight % to about 99 weight %, or to about 95 weight %, or to about 90 weight %, or to about 75 weight %, or to about 70 weight %, or to about 60 weight %, or to about 50 weight %, or to about 40 weight %, or to about 30 weight %, or to about 20 weight % of water.
[0042] The composition may be in solid form. The solid composition may be a powder composition or a granular composition. Such a composition may be agglomerated or spray dried. Such a composition may contain a plurality of granules or particles, and at least a part of those containing such granules or particles contains a different composition. The composition may be a powder cleaning composition or a granular cleaning composition, and these may contain a bleaching agent. The composition may be in the form of beads or lozenges, and these may be made from a liquid melt. The composition may be an extruded product.
[0043] The fabric and home care products may be in the form of unit dose articles such as tablets, pouches, sheets, or fibrous articles. Such pouches typically contain a water-soluble film that at least partially encloses the composition, for example, a polyvinyl alcohol water-soluble film. Suitable films are available from MonoSol, LLC (Indiana, USA). The composition can be enclosed in a single-compartment pouch or a multi-compartment pouch. The multi-compartment pouch may have at least 2, at least 3, or at least 4 compartments. The multi-compartment pouch may contain compartments arranged side by side and / or stacked. The composition contained in the pouch or its compartments may be liquid, solid (such as powder), or a combination thereof. The pouch composition may have a relatively low amount of water, for example, less than about 20 weight %, or less than about 15 weight %, or less than about 12 weight %, or less than about 10 weight %, or less than about 8 weight % of the composition.
[0044] The unit dosage article may be a flexible and soluble sheet. The flexible and soluble solid sheet may be porous and can be characterized by one or more of the following parameters. · A continuous bubble content of about 80% to 100%, preferably about 85% to 100%, more preferably about 90% to 100%, and / or · An overall average pore diameter of about 100 μm to about 2000 μm, about 150 μm to about 1000 μm, preferably about 200 μm to about 600 μm, and / or · An average bubble wall thickness of about 5 μm to about 200 μm, preferably about 10 μm to about 100 μm, more preferably about 10 μm to about 80 μm, and / or · A final moisture content of about 0.5 wt% to about 25 wt%, preferably about 1 wt% to about 20 wt%, more preferably about 3 wt% to about 10 wt% of the solid sheet article, and / or · A thickness of about 0.5 mm to about 4 mm, preferably about 0.6 mm to about 3.5 mm, more preferably about 0.7 mm to about 3 mm, even more preferably about 0.8 mm to about 2 mm, most preferably about 1 mm to about 1.5 mm, and / or · About 50 g / m 2 ~about 250 g / m 2 , preferably about 80 g / mm 2 ~about 220 g / m 2 , more preferably about 100 g / m 2 ~about 200 g / m 2 of the basis weight, and / or · About 0.05 g / cm 3 ~about 0.5 g / cm 3 , preferably about 0.06 g / cm 3 ~about 0.4 g / cm 3 , more preferably about 0.07 g / cm 3 ~about 0.2 g / cm 3 , most preferably about 0.08 g / cm 3 ~about 0.15 g / cm 3 of the density, and / or About 0.03 m 2 / g~about 0.25 m 2 / g, preferably about 0.04 m2 / g ~ about 0.22 m 2 / g, more preferably about 0.05 m 2 / g ~ about 0.2 m 2 / g, most preferably about 0.1 m 2 / g ~ about 0.18 m 2 characterized by a specific surface area of / g~
[0045] The flexible and soluble solid sheet may include, in addition to a polyvinyl alcohol (PVA) polymer or copolymer thereof as a film-forming agent, a structuring agent, a carrier for a surfactant, and optionally other active ingredients (e.g., emulsifiers, builders, chelating agents, fragrances, colorants, etc.). The PVA polymer or copolymer is preferably present in the flexible and soluble solid sheet in an amount in the range of about 5% to about 50%, preferably about 10% to about 40%, preferably about 15% to about 30%, more preferably about 20% to about 25% based on the total weight of the solid sheet. In a particularly preferred embodiment of the present invention, the total amount of PVA present in the flexible and soluble solid sheet article of the present invention is 25% or less based on the total weight of such a sheet article.
[0046] The PVA polymer or copolymer suitable for the practice of the present invention is selected to have a weight average molecular weight in the range of about 50,000 to about 400,000 daltons, preferably about 60,000 to about 300,000 daltons, more preferably about 70,000 to about 200,000 daltons, and most preferably about 80,000 to about 150,000 daltons. The weight average molecular weight is calculated by adding the average molecular weights of each polymer raw material and multiplying by the respective relative weight percentages by weight of the total weight of the polymer present in the porous solid.
[0047] A flexible and soluble solid sheet is preferably produced by first forming a wet premix containing PVA, a surfactant, and optionally other active ingredients, then shaping the wet premix into a sheet, and then drying the sheet of such wet premix to form a solid sheet article. Correspondingly, the weight average molecular weight of the PVA polymer or copolymer can affect the overall film-forming properties of the wet premix and the compatibility / incompatibility with the desired surfactant. Further, the weight average molecular weight of the PVA polymer or copolymer used herein may affect the viscosity of the wet premix, which in turn can affect various physical properties of the resulting solid sheet article thus formed.
[0048] The water-soluble unit dose article can include a multi-ply water-soluble fibrous structure. The fibrous structure can include one or more plies associated with each other to form a water-soluble fibrous structure. The water-soluble fibrous structure can include a plurality of fiber elements that are intertwined with each other or otherwise associated with each other so as to form the fibrous structure as such. Each ply within the fibrous structure can include one or more layers, and the layers together form the ply. The layer can include a plurality of fiber elements.
[0049] The fibrous structure can include at least one fabric colorant between a first ply and a second ply. The unit dose article can include a surfactant. In a non-limiting example, the fibrous structure can include a surfactant between a first ply and a second ply. In a non-limiting example, the first ply and / or the second ply and / or any other ply can include a surfactant.
[0050] The unit dose article 1 can dissolve under various washing conditions, for example, at low temperature, with low water volume and / or short washing cycles, and / or in cycles where the consumer over-loads the machine. The unit dose article 1 of the present invention may contain one or more active agents. As used herein, "active agent" refers to any component that can, either directly or indirectly, have an effect on one or more fabrics. The water-soluble unit dose article 1 may contain an insoluble substance that can be dispersed at a suspended average particle size of less than about 20 micrometers or less than about 50 micrometers under aqueous washing conditions. The particles can be active-containing particles. An advantage of such a unit dose article 1 of the present invention is that the unit dose article 1 dissolves sufficiently in the aqueous solution, and as a result, any active agent contained within the unit dose article 1 is released into the washing liquid without remaining in the substrate of the unit dose article 1. Another advantage of the unit dose article 1 of the present invention is the direct input of the unit dose article 1 such that the consumer can place one or more unit dose articles 1 into the washing machine drum without having to measure the product.
[0051] The water-soluble unit dose article, when measured by the thickness test method described herein, can exhibit a thickness of more than 0.01 mm, and / or more than 0.05 mm, and / or more than 0.1 mm, and / or about 100 mm or less, and / or about 50 mm or less, and / or about 20 mm or less, and / or about 10 mm or less, and / or about 5 mm or less, and / or about 2 mm or less, and / or about 0.5 mm or less, and / or about 0.3 mm or less. In a preferred but non-essential embodiment of the present invention, the unit dose article 1 of the present invention has a rectangular shape or a kite shape. Such a rectangular shape or kite shape is visually pleasing and comfortable for the consumer, and a plurality of articles of such a shape can be stacked and packaged together in a container for sale, which also features a similar rectangular shape or kite shape.
[0052] The water-soluble unit dose article, when measured according to the basis weight test method described herein, is about 500 grams / m 2 ~ about 5,000 grams / m 2 , preferably about 1,000 grams / m 2 ~ about 4,000 grams / m2 , more preferably about 1,500 grams / m 2 ~ about 3,500 grams / m 2 , most preferably about 2,000 grams / m 2 ~ about 3,000 grams / m 2 and may have a basis weight.
[0053] The composition may be in the form of a spray, for example, dispensed from a bottle via a trigger sprayer and / or an aerosol container having a valve.
[0054] In addition to the surfactant of formula I, the fabric and home care products may contain auxiliary materials depending on the intended form and / or end use. These auxiliaries may include, for example, additional surfactants, conditioning active substances, adhesion aids, rheology modifiers, structuring agents, bleaching systems, stabilizers, builders, chelating agents, migration inhibitors, dispersants, enzymes and enzyme stabilizers, catalytic metal complexes, polymer-based dispersants, clays and soil release / redeposition inhibitors, optical brighteners, foam suppressants, silicones, hue agents, aesthetic dyes, additional fragrances and fragrance delivery systems, structure elasticizers, carriers, hydrotropes, processing aids, structuring agents, antiagglomerants, coating agents, formaldehyde scavengers, organic solvents, washing polymers, and / or pigments.
[0055] The exact nature of these additional components and the concentration at which they are incorporated depend on the physical form of the composition and the nature of the operation being performed. However, when one or more auxiliaries are present, such one or more auxiliaries can be present as detailed below. The following is a non-limiting list of suitable additional auxiliaries.
[0056] The organic solvent may include alcohol and / or polyol. For example, the organic solvent may include ethanol, propanol, isopropanol, sugar alcohol, glycol, glycol ether, glycerin, or a combination thereof. The organic solvent may include polyethylene glycol, particularly low molecular weight polyethylene glycols such as PEG 200 and PEG 400; diethylene glycol; glycerol; 1,2-propanediol; polypropylene glycol including dipropylene glycol and tripropylene glycol, and low molecular weight polypropylene glycols such as PPG400; or a mixture thereof.
[0057] The chelating agent may include, for example, EDDS, HEDP, GLDA, DTPA, DTPMP, DETA, EDTA, MGDA, disodium 4,5-dihydroxybenzene-1,3-disulfonate [Tiron], or a mixture thereof. The chelating agent may be biodegradable. Examples of biodegradable chelating agents include, for example, GLDA, NTA, IDS, EDDG, EDDM, HIDS, HEIDA, HEDTA, DETA, or a combination thereof.
[0058] The enzyme may include, for example, protease, amylase, cellulase, mannanase, lipase, xyloglucanase, pectate lyase, nuclease enzyme, phosphodiesterase, or a mixture thereof.
[0059] Examples of the cleaning polymer may include those that can help clean stains or dirt on clothes and / or help prevent these stains from redepositing on clothes during washing. Examples are optionally modified polysaccharide, poly(vinyl-pyrrolidone), poly(ethylene glycol), poly(vinyl alcohol), poly(vinyl pyridine-N-oxide), poly(vinyl imidazole), or a combination thereof.
[0060] The composition may include one or more amphiphilic cleaning polymers. Such polymers have balanced hydrophilic and hydrophobic properties to remove grease particles from fabrics and surfaces. Suitable amphiphilic alkoxylated grease cleaning polymers include a core structure and a plurality of alkoxylate groups attached to the core structure. These may include alkoxylated polyalkyleneimines, particularly ethoxylated polyethyleneimines, or polyethyleneimines having an inner polyethylene oxide block and an outer polypropylene oxide block. Typically, these may be incorporated into the composition of the present invention in an amount of 0.005 wt% to 10 wt%, generally 0.5 wt% to 8 wt%.
[0061] The fabric and home care products of the present disclosure may include additional surfactants. Surfactants may be useful, for example, to provide cleaning benefits. The fabric and home care products may include a surfactant system that may contain one or more surfactants.
[0062] The fabric and home care products of the present disclosure may include a surfactant system in an amount of about 0.1 wt% to about 99 wt% of the composition, or about 2 wt% to about 80 wt%, or about 5 wt% to about 75 wt%. Liquid compositions may include a surfactant system in an amount of about 5 wt% to about 40 wt% of the composition. Compositions suitable for dense formulations, such as dense, liquid, gel, and / or unit dose forms, may include a surfactant system in an amount of about 25 wt% to about 70 wt%, or about 30 wt% to about 50 wt% of the composition.
[0063] The surfactant system may include anionic surfactants, nonionic surfactants, zwitterionic surfactants, cationic surfactants, amphoteric surfactants, or combinations thereof. The surfactant system may include linear alkylbenzene sulfonates, alkyl ethoxylated sulfates, alkyl sulfates, nonionic surfactants such as ethoxylated alcohols, amine oxides, or mixtures thereof. The surfactants may be at least partially derived from natural resources such as natural feedstock alcohols.
[0064] Suitable anionic surfactants may include any conventional anionic surfactant. This may include, for example, sulfate detergency surfactants for alkoxylated and / or non-alkoxylated alkyl sulfate materials, and / or sulfonic acid-based detergency surfactants, such as alkylbenzene sulfonate. The anionic surfactant may be linear, branched, or a combination thereof. Preferred surfactants include linear alkylbenzene sulfonate (LAS), alkyl ethoxylated sulfate (AES), alkyl sulfate (AS), or mixtures thereof. Other suitable anionic surfactants include branched modified alkylbenzene sulfonate (MLAS), methyl ester sulfonate (MES), sodium lauryl sulfate (SLS), sodium lauryl ether sulfate (SLES), alkyl ethoxylated carboxylate (AEC), and / or glycolipids such as rhamnolipids and / or sophorolipids. The anionic surfactant may be present in acid form, salt form, or mixtures thereof. The anionic surfactant may be partially or wholly neutralized, for example, by an alkali metal (e.g., sodium) or an amine (e.g., monoethanolamine).
[0065] The fabric and home care products may also contain a branched alkyl sulfate surfactant. The branched alkyl sulfate may include a 2-alkyl branched alkyl alcohol. The 2-alkyl branched alcohol is a positional isomer in which the position of the hydroxymethyl group (consisting of a methylene bridge (-CH2- unit) bonded to a hydroxy (-OH) group) on the carbon chain varies. Thus, the 2-alkyl branched alkyl alcohol generally consists of a mixture of positional isomers. Further, it is well known that aliphatic alcohols and surfactants such as 2-alkyl branched alcohols are characterized by a chain length distribution. In other words, aliphatic alcohols and surfactants generally consist of a blend of molecules having different alkyl chain lengths (although it is possible to obtain a single chain length fraction). In particular, the 2-alkyl primary alcohols described herein, which may have a specific alkyl chain length distribution and / or a specific proportion of certain positional isomers, cannot be obtained by simply blending commercially available materials. Specifically, a distribution of surfactants of about 50 wt% to about 100 wt% having m + n = 11 cannot be achieved by blending commercially available materials.
[0066] The branched alkyl sulfate may essentially consist of a mixture of a surfactant isomer of Formula 3 and a surfactant of Formula 4.
[0067]
Chemical formula
[0068] The surfactant system may contain a nonionic surfactant. Suitable nonionic surfactants include alkoxylated aliphatic alcohols such as ethoxylated aliphatic alcohols. Other suitable nonionic surfactants include alkoxylated alkylphenols, alkylphenol condensates, medium-chain branched-chain alcohols, medium-chain branched-chain alkyl alkoxylates, alkyl polysaccharides (e.g., alkyl polyglycosides), polyhydroxy fatty acid amides, poly(oxyalkylated) alcohol surfactants protected at the ends with ethers, and mixtures thereof. The alkoxylate units may be ethyleneoxy units, propyleneoxy units, or mixtures thereof. The nonionic surfactant may be linear, branched-chain (e.g., medium-chain branched), or a combination thereof. Certain nonionic surfactants may include alcohols having an average of about 12 to about 16 carbons and an average of about 3 to about 9 ethoxy groups, such as a C12-C14 EO7 nonionic surfactant.
[0069] The nonionic surfactant may have the formula R(OC2H4) n OH, wherein R is selected from the group consisting of aliphatic hydrocarbon radicals containing from about 8 to about 16 carbon atoms, and the average value of n is from about 5 to about 15. For example, the nonionic surfactant may be selected from ethoxylated alcohols having an average of about 12 to 14 carbon atoms in the alcohol (alkyl portion) and an average degree of ethoxylation of about 7 to 9 moles of ethylene oxide per mole of alcohol.
[0070] Additional non-limiting examples include the formula R(OC2H4) n OH (wherein R contains an alkylphenyl radical having an alkyl group of about 8 to about 12 carbon atoms and the average value of n is from about 5 to about 15), ethoxylated alkylphenols, C such as the NEODOL® nonionic surfactant manufactured by Shell 12 ~C 18 alkyl ethoxylates; C 14 ~C 22 medium-chain branched alcohols; C 14 ~C 22Examples of medium-branched alkyl ethoxylates include BAEx (where x ranges from 1 to 30). The nonionic ethoxylated alcohol surfactants herein may further contain residual alkoxylation catalysts, which can be regarded as residues or impurities from the reaction. It may further contain various impurities or by-products of the alkoxylation reaction. The impurities can vary depending on the catalyst used and the reaction conditions. Examples of impurities include alkyl ethers such as dialkyl ethers like didodecyl ether, glycols such as diethylene glycol, triethylene glycol, pentaethylene glycol, and other polyethylene glycols.
[0071] Nonionic ethoxylated alcohols can be a narrow range of ethoxylated alcohols. The narrow range of ethoxylated alcohols can have the following general formula (5):
[0072] [Chemical formula] (wherein R is selected from saturated or unsaturated, straight-chain or branched C8 - C 20 alkyl groups, and more than 90% of n is 0 ≦ n ≦ 15). Additionally, the average value of n can be from about 4 to about 14, preferably from about 6 to about 10, less than about 10% by weight of the alcohol ethoxylate is an ethoxylate with n < 7, and 10% to about 20% by weight of the alcohol ethoxylate is an ethoxylate with n = 8.
[0073] The composition may contain an average value of n of about 10. The composition can have the following ranges for each of the following values of n: n = 0 is at most 5%, n = 1, 2, 3, 4, 5 are each at most 2%, n = 6 is at most 4%, n = 7 is at most 10%, n = 8 is 12% - 20%, n = 9 is 15% - 25%, n = 10 is 15% - 30%, n = 11 is 10% - 20%, n = 12 is at most 10%, n > 12 is at most 10%. The composition may have n from 9 to 10 at 30% - 70%. The composition may have n from 8 to 11 for more than 50% of its composition.
[0074] R can be selected from saturated or unsaturated, straight-chain or branched C12-C16 alkyl groups, and the average value of n is from about 6 to about 10. R can also be a saturated or unsaturated, straight-chain or branched C8-C 20 alkyl group, more than 90% of n is 0 ≦ n ≦ 15, the average value of n is from about 5 to about 10, and less than about 20% by weight of the alcohol ethoxylate is an ethoxylate having n < 8. R can also be a saturated or unsaturated, straight-chain or branched C8-C 20 alkyl group, more than 90% of n is 0 ≦ n ≦ 15, the average value of n is from about 6 to about 10, less than about 10% by weight of the alcohol ethoxylate is an ethoxylate having n < 7, and 10% to about 20% by weight of the alcohol ethoxylate is an ethoxylate having n = 8.
[0075] The alcohol ethoxylates described herein are typically not a single compound as suggested by their general formula (5), rather, the alcohol ethoxylates comprise a mixture of several homologues having various polyalkylene oxide chain lengths and molecular weights. Among the homologues, those close to the alkylene oxide adduct with the most predominant number of total alkylene oxide units per mole of alcohol are desirable, and homologues with a much smaller or much larger number of total alkylene oxide units than the alkylene oxide adduct with the most predominant number are less desirable. In other words, a "narrow range" or "peaked" alkoxylated alcohol composition is desirable. A "narrow range" or "peaked" alkoxylated alcohol composition refers to an alkoxylated alcohol composition with a narrow distribution of the number of moles of alkylene oxide added.
[0076] "Narrow range" or "peaked" alkoxylated alcohol compositions may be desirable for selected applications. Homologues within the distribution range for the selected purpose may have an appropriate lipophilic-hydrophilic balance for the selected application. For example, in the case of an ethoxylated alcohol product containing an average ratio of 5 ethylene oxide (EO) units per molecule, the homologues having the desired lipophilic-hydrophilic balance may be in the range of 2 EO to 9 EO. Homologues having shorter EO chain lengths (<2 EO) or longer EO chain lengths (>9 EO) may not be desirable for applications where such longer and shorter homologues are too lipophilic or too hydrophilic for the applications utilizing this product, and thus may not be desirable for applications where a surfactant with an α = 5 EO / alcohol ratio is typically selected. Therefore, it is advantageous to develop alkoxylated alcohols having a peaked distribution.
[0077] The narrow range of the alkoxylated alcohol compositions of the present disclosure may have an average degree of ethoxylation in the range of about 0 to about 15, such as in the ranges of about 4 to about 14, about 5 to 10, about 8 to 11, and about 6 to 9. The narrow range alkoxylated alcohol compositions of the present disclosure may have an average degree of ethoxylation of 10. The narrow range alkoxylated alcohol compositions of the present disclosure may have an average degree of ethoxylation of 9. The narrow range alkoxylated alcohol compositions of the present disclosure may have an average degree of ethoxylation of 5.
[0078] The above ranges are exemplified in the column of Novel 1214-9 in Table A. As shown in Table A below, samples were derivatized with a DMF-SO3 complex and then analyzed by LCMS ESI(-) and LCMS ESI(+). The relative abundances % are listed in the following table. The relative abundance ratio is the weighted average of each ethoximer with respect to the total abundance of all ethoximers in the sample.
[0079]
Table 1
[0080] Note that LCMS-ESI(+) is not sensitive to less than 3 moles of ethoxymers or free alcohols. Additionally, ethoxymers of 3 to 5 moles are underestimated. Typically, when the average distribution of EO is greater than 7 moles of EO, the distribution is not much affected by this sensitivity limit. Additionally, LCMS-ESI(-) may underestimate heavier ethoxymers when the distribution is very broad, such as in the case of ALFONIC samples. Therefore, ALFONIC samples were analyzed in both + / - modes and averaged.
[0081] Suitable zwitterionic surfactants include betaines such as alkyldimethylbetaine and coco dimethylamidopropyl betaine, C8-C 18 (e.g., C 12 -C 18 ) amine oxides (e.g., C 12 - 14 dimethylamine oxide), and / or N-alkyl-N,N-dimethylamino-1-propanesulfonates (where the alkyl group may be C8-C 18 or C 10 -C 14 ) and any conventional zwitterionic surfactants such as sulfo and hydroxybetaines. The zwitterionic surfactant may contain amine oxide.
[0082] The fabric and home care products further comprise from 0.5 wt% to 20 wt%, more preferably from 0.75 wt% to 15 wt%, more preferably from 1 wt% to 10 wt%, and most preferably from 1 wt% to 5 wt% of an alkyl polyglycoside ("APG") surfactant of the surfactant system. Preferably, the alkyl polyglycoside surfactant is a C8-C16 alkyl polyglycoside surfactant, preferably a C8-C14 alkyl polyglycoside surfactant, and preferably has an average degree of polymerization of 0.1-3, more preferably 0.5-2.5, even more preferably 1-2. Most preferably, the alkyl polyglycoside surfactant has an average degree of polymerization of 0.5-2.5, preferably 1-2, and most preferably 1.2-1.6, and an average alkyl carbon chain length of 10-16, preferably 10-14, and most preferably 12-14. C8-C16 alkyl polyglucosides are commercially available from several suppliers (e.g., Simusol® surfactant from Seppic Corporation, and Glucopon® 600 CSUP, Glucopon® 650 EC, Glucopon® 600 CSUP / MB, and Glucopon® 650 EC / MB from BASF Corporation).
[0083] Depending on the formulation and / or the intended end use, the composition may substantially not contain a particular surfactant. For example, a liquid fabric enhancing composition such as a fabric softener may substantially not contain an anionic surfactant because such a surfactant can have a negative interaction with the cationic component.
[0084] The compositions of the present disclosure may contain a conditioning active. Compositions containing a conditioning active may provide benefits regarding softness, wrinkle prevention, antistatic, conditioning, anti-elongation, color, and / or appearance.
[0085] The conditioning active substance may be present at a level of about 1% to about 99% by weight of the composition. The composition may contain from about 1% by weight, or from about 2% by weight, or from about 3% by weight of the composition up to about 99% by weight, or up to about 75% by weight, or up to about 50% by weight, or up to about 40% by weight, or up to about 35% by weight, or up to about 30% by weight, or up to about 25% by weight, or up to about 20% by weight, or up to about 15% by weight, or up to about 10% by weight of the conditioning active substance. The composition may contain from about 5% to about 30% by weight of the conditioning active substance of the composition.
[0086] Suitable conditioning active substances for the compositions of the present disclosure include quaternary ammonium ester compounds, silicones, non-ester quaternary ammonium compounds, amines, fatty acid esters, sucrose esters, silicones, dispersible polyolefins, polysaccharides, fatty acids, softening or conditioning oils, polymer latexes, or combinations thereof.
[0087] This composition may contain a quaternary ammonium ester compound, a silicone or a combination of a plurality of these, preferably a combination of one set. The total amount of the quaternary ammonium ester compound and the silicone may be from about 5% to about 70% by weight, or from about 6% to about 50% by weight, or from about 7% to about 40% by weight, or from about 10% to about 30% by weight, or from about 15% to about 25% by weight of the composition. The composition may contain the quaternary ammonium ester compound and the silicone in a weight ratio of about 1:10 to about 10:1, or about 1:5 to about 5:1, or about 1:3 to about 1:3, or about 1:2 to about 2:1, or about 1:1.5 to about 1.5:1, or about 1:1.
[0088] The composition may contain a mixture of different types of conditioning actives. The compositions of the present disclosure may contain specific conditioning actives, but may be substantially free of other conditioning actives. For example, the composition may be free of quaternary ammonium ester compounds, silicones, or both. The composition may contain a quaternary ammonium ester compound, but may be substantially free of silicones. The composition may contain silicones, but may be substantially free of quaternary ammonium ester compounds.
[0089] The compositions of the present disclosure may contain an adhesion aid. The adhesion aid may promote the adhesion of delivery particles, conditioning actives, fragrances, or combinations thereof, improve the performance effects of the composition, and / or enable more efficient incorporation of such beneficial agents. The composition may contain from 0.0001 wt% to 3 wt%, preferably from 0.0005 wt% to 2 wt%, more preferably from 0.001 wt% to 1 wt%, or from about 0.01 wt% to about 0.5 wt%, or from about 0.05 wt% to about 0.3 wt% of the adhesion aid based on the composition. The adhesion aid may be a cationic or amphoteric polymer, preferably a cationic polymer.
[0090] General cationic polymers and methods for their manufacture are well known in the literature. Suitable cationic polymers include quaternary ammonium polymers known as "polyquaternium" polymers named according to the International Nomenclature of Cosmetic Ingredients, such as polyquaternium-6 (poly(diallyldimethylammonium chloride)), polyquaternium-7 (copolymer of acrylamide and diallyldimethylammonium chloride), polyquaternium-10 (quaternized hydroxyethyl cellulose), polyquaternium-22 (copolymer of acrylic acid and diallyldimethylammonium chloride), and the like.
[0091] The adhesion aid may be selected from the group consisting of polyvinylformamide, partially hydroxylated polyvinylformamide, polyvinylamine, polyethyleneimine, ethoxylated polyethyleneimine, polyvinyl alcohol, polyacrylate, and combinations thereof. The cationic polymer may include a cationic acrylate.
[0092] The adhesion aid can be added to the fabric treatment composition simultaneously with the delivery particles (e.g., simultaneously with the encapsulated beneficial agent) or directly / independently. The weight average molecular weight of the polymer, when measured by size exclusion chromatography relative to a polyethylene oxide standard using refractive index (RI) detection, may be from 500 Daltons to 5,000,000 Daltons, or from 1000 Daltons to 2,000,000 Daltons, or from 2500 Daltons to 1,500,000 Daltons. The weight average molecular weight of the cationic polymer may be from 5000 Daltons to 37,500 Daltons.
[0093] The compositions of the present disclosure may include a rheology modifier and / or a structuring agent. The rheology modifier may be used to "thicken" or "thin" the liquid composition to a desired viscosity. The structuring agent may be used to promote phase stability and / or to suspend particles in the liquid composition such as the delivery particles described herein or to inhibit their aggregation.
[0094] Suitable rheology modifiers and / or structuring agents include non-polymeric crystalline hydroxyl-functional structuring agents (including those based on hydrogenated castor oil), polymeric structuring agents, cellulose fibers (e.g., microfibrillated cellulose derivable from bacterial, fungal, or plant origin including wood), diamide gelling agents, or combinations thereof.
[0095] The polymer structuring agent may be of natural or synthetic origin. The polymer structuring agent of natural origin may include hydroxyethyl cellulose, hydrophobically modified hydroxyethyl cellulose, carboxymethyl cellulose, polysaccharide derivatives, and mixtures thereof. The polysaccharide derivatives may include pectin, alginate, arabinogalactan (gum arabic), carrageenan, gellan gum, xanthan gum, guar gum, and mixtures thereof. The synthetic polymer structuring agent may include polycarboxylate, polyacrylate, hydrophobically modified ethoxylated urethane, hydrophobically modified nonionic polyol, and mixtures thereof. The polycarboxylate polymer may include polyacrylate, polymethacrylate, or mixtures thereof. The polyacrylate may include a copolymer of an unsaturated monocarboxylic acid or dicarboxylic acid and a C1-C 30 alkyl ester of (meth)acrylic acid. Such a copolymer is available from Noveon inc under the trade name Carbopol Aqua 30. Another suitable structuring agent is sold under the trade name Rheovis CDE available from BASF.
[0096] The composition of the present invention may further comprise an amphiphilic alkoxylated polyalkyleneimine, and mixtures thereof, preferably an amphiphilic polymer selected from the group consisting of amphiphilic alkoxylated polyalkyleneimines, in an amount of about 0.01 wt% to about 5 wt%, preferably about 0.05 wt% to about 2 wt%, more preferably about 0.07 wt% to about 1 wt% of the total composition.
[0097] Preferably, the amphiphilic alkoxylated polyalkyleneimine is an alkoxylated polyethyleneimine polymer comprising a polyethyleneimine main chain having an average molecular weight range of 100 to 5,000, preferably 400 to 2,000, more preferably 400 to 1,000 daltons, and the alkoxylated polyethyleneimine polymer is (i) One or two alkoxylation modifications per nitrogen atom by a polyalkoxylene chain having an average of about 1 to about 50 alkoxy moieties per modification, wherein the terminal alkoxy moiety of the alkoxylation modification is capped with hydrogen, C1-C4 alkyl, or a mixture thereof, the alkoxylation modification, (ii) The addition of one C1-C4 alkyl moiety and one or two alkoxylation modifications per nitrogen atom by a polyalkoxylene chain having an average of about 1 to about 50 alkoxy moieties per modification, wherein the terminal alkoxy moiety is capped with hydrogen, C1-C4 alkyl, or a mixture thereof, the alkoxylation modification, or (iii) Further comprising combinations thereof, The alkoxy moiety includes ethoxy (EO) and / or propoxy (PO) and / or butoxy (BO). When the alkoxylation modification includes EO, it also includes PO or BO.
[0098] Preferred amphiphilic alkoxylated polyethyleneimine polymers contain EO groups and PO groups in the alkoxylated chain. The PO groups are preferably present at the terminal positions of the alkoxy chain, and the alkoxylated chain is preferably protected at the terminal with hydrogen. Optionally, within the scope of the present invention, hydrophilic alkoxylated polyethyleneimine polymers containing only ethoxy (EO) units in the alkoxylated chain may also be incorporated.
[0099] Preferred polyethyleneimine has a general structure of formula (II),
[0100]
Chemical formula
[0101] Another polyethyleneimine has the general structure of formula (II), but the weight-average molecular weight of the polyethyleneimine main chain is about 600, the average of n in formula (II) is about 24, the average of m in formula (II) is about 16, R in formula (II) is selected from hydrogen, C1-C4 alkyl, and mixtures thereof, preferably hydrogen. The degree of permanent quaternization of formula (II) can be from 0% to about 22% of the nitrogen atoms of the polyethyleneimine main chain. The molecular weight of this polyethyleneimine is preferably 25,000-30,000.
[0102] The most preferred polyethyleneimine has the general structure of formula (II), the weight-average molecular weight of the polyethyleneimine main chain is about 600, the average of n in formula (II) is about 24, the average of m in formula (II) is about 16, and R in formula (II) is hydrogen. The degree of permanent quaternization of formula (II) is 0% of the nitrogen atoms of the polyethyleneimine main chain. The molecular weight of this polyethyleneimine is preferably about 25,000-30,000, most preferably about 28,000.
[0103] The composition of the present invention may contain about 0.05 wt% to about 2 wt%, preferably about 0.1 wt% to about 1.5 wt%, or more preferably about 0.5 wt% to about 1 wt% of salt, preferably monovalent, divalent inorganic salts or mixtures thereof, more preferably sodium chloride, sodium sulfate or mixtures thereof, most preferably sodium chloride, based on the total composition.
[0104] The composition of the present invention may contain, based on the weight of the whole composition, about 0.1% to about 10% by weight, or preferably about 0.5% to about 10% by weight, or more preferably about 1% to about 10% by weight of a hydrotrope or a mixture thereof, preferably sodium cumenesulfonate.
[0105] The composition of the present invention may contain an organic solvent. Suitable organic solvents include C4 - 14 ethers and diethers, polyols, glycols, alkoxylated glycols, C6 - C16 glycol ethers, alkoxylated aromatic alcohols, aromatic alcohols, aliphatic straight-chain or branched alcohols, alkoxylated aliphatic straight-chain or branched alcohols, alkoxylated C1 - C5 alcohols, C8 - C14 alkyl and cycloalkyl hydrocarbons and halohydrocarbons, and mixtures thereof. Preferably, the organic solvent includes alcohols, glycols, and glycol ethers, or alcohols and glycols. The present composition contains 0% to less than about 50% by weight, preferably about 0.01% to about 25% by weight, more preferably about 0.1% to about 10% by weight, or most preferably about 0.5% to about 5% by weight of an organic solvent, preferably an alcohol, more preferably ethanol, a polyalkylene glycol, more preferably polypropylene glycol, and mixtures thereof.
[0106] Data Compositions containing the surfactant of formula I as described above are tested to determine whether there are advantages in stain removal by their use. To observe stain removal, a technical stain removal washing procedure is used. This method is described below.
[0107] As shown in Table 1 below, several different stain types are outlined. The results show better or equivalent stain removal by the use of the surfactant of formula I (Compositions B - D of the present invention, Example section) compared to the sodium lauryl sulfate surfactant in a conventional liquid detergent composition such as Comparative Composition A (Example section).
[0108]
Table 2
[0109] Follow the technical stain removal washing procedure described below. 0.66 grams of soluble unit dose detergent E-H was added at 15 °C to a Tergotometer pot containing 1 L of test wash liquor + test fabric, soiled SBL fabric, and clean fabric ballast, stirred at 208 rpm for 17 minutes at 7 US grains per gallon, and centrifuged. The fabric was then rinsed at 15 °C with water at 7 US grains / gallon at 200 rpm for 5 minutes and centrifuged. After rinsing, the fabric was placed in a high position for 40 minutes to dry and then analyzed.
[0110] The stain removal index score for each stain is calculated as described below and listed in Table 2 below. These results show better or equivalent stain removal by use of the surfactant of formula I (Compositions F - G of the present invention, Examples section) compared to the branched C15 alkyl sulfate surfactant in a soluble unit dose detergent such as Comparative Composition E (Examples section).
[0111] [Table 3]
[0112] Method Technical stain removal washing procedure The method involves using a Tergotometer to simulate the washing of fabric in a washing machine. Using the test formulations, a technical stain specimen (9 grams) was washed together with soiled SBL fabric (4 grams) and clean knitted cotton ballast (47 grams). Technical stain specimens of CW120 cotton with stains were purchased from Advanced Product Design Co., Inc (Cincinnati, OH). The washing tests consisted of two internal replicates and four external replicates for each of the stain types and treatments described above.
[0113] 2.37 grams of liquid detergents A - D (the following comparative composition A and the compositions B - D of the present invention) were added to a tergotometer pot at 15 °C with 1 L of test wash solution + test fabric, soiled fabric, and clean fabric ballast, stirred at 208 rpm for 17 minutes at 7 US grains per gallon, and centrifuged. The fabric was then rinsed at 15 °C with water at 7 US grains / gallon at 200 rpm for 5 minutes and centrifuged. After rinsing, the fabric was dried in a high position for 40 minutes and then analyzed.
[0114] Using image analysis, each stain was compared to a control sample of non - stained fabric. The software converted the resulting images to standard color values, compared them to reference values based on the commonly used Macbeth color retention chart, and assigned color values (stain levels) to each stain. Two internal replicates and four external replicates were prepared for each.
[0115] Stain removal from the samples was measured as follows.
[0116]
Number
[0117]
Table 4
[0118]
Table 5
[0119] Liquid compositions such as the above liquid detergent compositions can be prepared by combining the components in any conventional order, mixing the resulting combination of components, for example by stirring, to form a phase-stable liquid detergent composition. In a process for preparing such a composition, for example, a liquid matrix can be formed that contains at least a majority, or even substantially all, of the liquid components such as surfactants, non-surfactant liquid carriers, and other optional liquid components, and the liquid components are sufficiently mixed by applying shear stirring to this combination of liquids. For example, high-speed stirring by a mechanical stirrer can be usefully employed.
[0120] While maintaining shear stirring, substantially all of any anionic surfactant and solid form components can be added. Stirring of the mixture is continued and, if necessary, enhanced at that point to form a solution or homogeneous dispersion of insoluble solid phase particles in the liquid phase. After adding some or all of the solid form material, particles of any enzyme material to be included, for example, enzyme prills, can be incorporated. As a variation of the above-described composition preparation procedure, one or more of the solid components may be added to the stirred mixture as a solution or slurry of particles pre-mixed with a minor portion of one or more of the liquid components. After all of the composition components have been added, stirring of the mixture is continued for a time sufficient to form a composition having the required viscosity and phase stability characteristics. Often, this involves stirring for a period of about 30 to 60 minutes.
[0121] Examples of water-soluble unit doses The following are exemplary water-soluble unit dose formulations. The composition may be part of a single-chamber water-soluble unit dose article or may be divided over multiple compartments to result in the following "averaged over the compartments" total article composition. The following compositions are encapsulated in a water-soluble film comprising a polyvinyl alcohol-based water-soluble film, more specifically, a blend of a polyvinyl alcohol homopolymer and a carboxylated anionic polyvinyl alcohol copolymer, or a water-soluble film comprising a carboxylated anionic polyvinyl alcohol copolymer such as M8630 or M8310 manufactured by MonoSol.
[0122]
Table 6
[0123]
Table 7
[0124]
Chemical formula
[0125] The following is a multi - compartment water - soluble single - dose laundry article having a larger lower compartment with two smaller compartments in a side - by - side configuration stacked on top of the bottom compartment, according to the design of the Ariel 3 - in - 1 pod as sold annually in the UK in January 2020. The following composition is enclosed in a water - soluble outer film based on polyvinyl alcohol, more specifically, a water - soluble film containing a blend of a polyvinyl alcohol homopolymer and a carboxylated anionic polyvinyl alcohol copolymer, and a blend of polyvinyl alcohol homopolymers, or a water - soluble intermediate film containing a blend of a polyvinyl alcohol homopolymer and a carboxylated anionic polyvinyl alcohol copolymer.
[0126]
Table 8
[0127]
Chemical formula
[0128] Examples of fiber - based water - soluble unit dosages The fiber - water - soluble unit dosage containing the first layer of fiber elements can be spun using the first spinning beam and recovered on a forming belt. Then, the forming belt having the first layer of fibers is passed under a second spinning beam modified with a particle addition system. The particle addition system can substantially inject particles towards a landing zone on the forming belt directly below the fiber elements from the second spinning beam. Suitable particle addition systems can be assembled from particle feeders such as vibratory, belt or screw feeders, and injection systems such as air knives or other fluidized conveying systems. To assist in the consistent distribution of particles in the transverse direction, preferably, the particles are supplied over a width approximately the same as the spinning die to ensure that the particles are delivered across the entire width of the composite structure. Preferably, the particle feeder is completely enclosed except for the outlet to minimize the breakage of the particle feed material. By the co - collision of the particles and the fiber elements on the forming belt under the second spinning beam, particle packing is expanded and a composite structure is created in which the fibers substantially penetrate the inter - particle pores.
[0129] The following table describes non-limiting examples of the dried fiber compositions of the present invention that can be used to produce fiber elements. To produce the fiber elements, an aqueous solution, preferably an aqueous solution having a solids content of about 45% to 60%, is processed by one or more spinning beams. Suitable spinning beams include a capillary die having an elongating air stream and a drying air stream suitable for substantially drying the elongated fibers before they impinge on a forming belt.
[0130] [Table 9]
[0131] The following table shows non-limiting examples of particulate compositions. The particles can be produced by various suitable processes including grinding, spray drying, agglomeration, extrusion, granulation, encapsulation, tableting, and any combination thereof. One or more particles may be mixed with each other prior to addition.
[0132] [Table 10]
[0133] The resulting products are illustrated in the table below, and using the undiluted chassis composition for the products, details of the structure of the product chassis by the fiber and particle components are provided. Note that other product auxiliary materials such as fragrances, enzymes, foam suppressants, bleaching agents, etc. may be added to the chassis.
[0134] [Table 11]
[0135] LAS is a linear alkylbenzene sulfonate with an average aliphatic carbon chain length of C 11 ~C 12 supplied by Stepan, Northfield, Illinois, USA or Huntsman Corp. HLAS is in the acid form.
[0136] AS is C supplied by Stepan (Northfield, Illinois, USA). 12~14 sulfate, and / or mid-chain branched alkyl sulfate.
[0137] The dispersant polymer (Disp. polymer) has a molecular weight of 70,000 and an acrylate:maleate ratio of 70:30 and is supplied by BASF, Ludwigshafen, Germany.
[0138] The PEG-PVAc polymer is a polyvinyl acetate-grafted polyethylene oxide copolymer having a polyethylene oxide main chain and a plurality of polyvinyl acetate side chains. The molecular weight of the polyethylene oxide backbone chain is about 6,000, the weight ratio of polyethylene oxide to polyvinyl acetate is about 40 - 60, and there is 1 or less graft point per 50 ethylene oxide units. It is sold by BASF (Ludwigshafen, Germany).
[0139] Ethoxylated polyethyleneimine (PE20) is a polyethyleneimine core with a molecular weight of 600 g / mol having 20 ethoxylate groups per -NH. It is sold by BASF (Ludwigshafen, Germany).
[0140] Liquid dishwashing detergent formulation The following is an exemplary liquid dishwashing detergent formulation. The formulation can be made by standard mixing of the individual components.
[0141]
Table 12
[0142] Exemplary method for making the surfactant of formula I The process for preparing the surfactant of formula I starts from a mixture of Ar-COOH (II) and R3-CH2-COOH (III) to produce an arylaliphatic ketone of formula IV: Ar-C(=O)-CH2-R3 (IV), where Ar and R3 are as defined above and in the claims. This process further includes derivatizing the arylaliphatic ketone of formula IV: Ar-C(=O)-CH2-R3 (IV) by a hydrogenation-sulfation sequence (option a) or a sulfonation-hydrogenation sequence (option b) to produce a compound of formula I.
[0143] R1 is OSO3X, where X is as defined above and in the claims, R2 is H, and R3 is C6-C 16 For the compound of formula I where R3 is an aliphatic group, this process is carried out according to option a, which includes the following steps. a. Obtaining an arylaliphatic ketone of formula IV: Ar-C(=O)-CH2-R3 (IV) [where Ar and R3 are as defined above] by decarboxylative cross-ketonization between Ar-COOH (II) and R3-CH2-COOH (III) [where Ar and R3 are as defined above]. b. Hydrogenating the arylaliphatic ketone of formula IV obtained in step a in the presence of H2 and a catalyst to obtain a secondary alcohol of formula V: Ar-CH(OH)-CH2-R3 (V) [where Ar and R3 are as defined above]. c. Sulfating the secondary alcohol of formula V obtained in step b with a sulfating agent and subsequently neutralizing with XOH or X(OH).
[0144] R1 is OH, R2 is SO3X, X is as defined above and in the claims, and R3 is C6-C 16 The first compound of formula I; Or R1 is H, R2 is SO3X, X is as defined above and in the claims, and R3 is an aliphatic C6-C 16 The second compound of formula I; For the preparation of a mixture of the first and second compounds of formula I, the process is carried out according to alternative b, which comprises the following steps. a. Obtaining an aryl aliphatic ketone of formula IV: Ar-C(=O)-CH2-R3 (IV), where Ar and R3 are as defined above, by decarboxylative cross-ketonization between Ar-COOH (II) and R3-CH2-COOH (III) [where Ar and R3 are as defined previously]. b. Sulfonating the aryl aliphatic ketone of formula IV obtained in step a with a sulfonating agent and subsequently neutralizing with XOH or X(OH) to obtain an aryl aliphatic ketone sulfonate of formula VI: Ar-C(=O)-CH(SO3X)-R3 (VI), where Ar, X, and R3 are as defined above. c. Hydrogenating the aryl aliphatic ketone sulfonate in the presence of H2 and a catalyst.
[0145] Step a - Decarboxylative cross-ketonization The decarboxylative cross-ketonization reaction according to step a of the process between the aryl carboxylic acid Ar-COOH (II) and the aliphatic carboxylic acid R3-CH2-COOH (III) provides an aryl aliphatic ketone of formula IV: Ar-C(=O)-CH2-R3 (IV), where Ar and R3 are as defined above and as defined in the foregoing and in the claims, and forms part of both alternatives a and b of the process.
[0146] The starting materials Ar-COOH (II) and R3-CH2-COOH (III) used in the process of the invention are commercially available or can be synthesized by a person skilled in the art taking into account their common general knowledge.
[0147] Decarboxylative cross-ketonization is preferably carried out as catalytic decarboxylative cross-ketonization. Such a procedure is known from WO 2018 / 229285 (A1) (see, for example, pages 4, lines 9 - 34 of WO 2018 / 229285 (A1)). The catalytic decarboxylative cross-ketonization of aryl and aliphatic carboxylic acids described in detail in WO 2018 / 229285 (A1) can be applied equally in the context of this specification to provide aryl aliphatic ketones of formula IV: Ar-C(=O)-CH2-R3 (IV).
[0148] A person skilled in the art can, taking into account their common general knowledge, modify the decarboxylative cross-ketonization procedure applied in the art for the purposes of this process, if necessary.
[0149] Option a: Steps b and c - Hydrogenation - Sulfation - Neutralization The order of hydrogenation - sulfation by steps b and c of option a of this process is further described below.
[0150] Step b of option a: In the process according to option a, the aryl aliphatic ketone of formula IV: Ar-C(=O)-CH2-R3 (IV) is hydrogenated in the presence of H2 and a catalyst, whereby a secondary alcohol of formula V: Ar-CH(OH)-CH2-R3 (V) is obtained, wherein Ar and R3 are as defined above and in the claims.
[0151] The catalytic hydrogenation of aryl aliphatic ketones to obtain the corresponding aryl aliphatic alcohols is a standard reaction generally known to those skilled in the art.
[0152] In this process, the hydrogenation step is carried out in the presence of a metal-based catalyst, preferably a transition metal-based catalyst, typically palladium on charcoal (Pd / C).
[0153] In this process, the hydrogenation step can be carried out in a reactor / autoclave at a hydrogen gas (H2) pressure of up to 100 bar (such as 80 bar, 60 bar, 40 bar or 20 bar etc.), at a temperature of up to 150 °C, preferably up to 100 °C, such as 90 °C etc.
[0154] Catalytic hydrogenation can be carried out in solution using an additional solvent. In that case, a person skilled in the art can select a suitable solvent from the range of standard solvents widely used in organic synthesis taking into account their common general knowledge. Examples of typical solvents used in the catalytic hydrogenation reaction include, for example, methanol, ethanol, isopropanol, tert-butanol, THF, Me-THF, saturated hydrocarbons, or mixtures thereof.
[0155] The reaction can also be carried out without a solvent. In that case, catalytic hydrogenation is typically carried out at a temperature at which the substrate is in a molten form.
[0156] A person skilled in the art can control the progress of the reaction using standard techniques such as NMR taking into account their general knowledge.
[0157] A person skilled in the art can use general purification and separation techniques such as distillation, precipitation / crystallization methods (where applicable), and chromatography methods (including, for example, flash chromatography and HPLC) taking into account their common general knowledge to purify the product mixture obtained from the hydrogenation step.
[0158] Procedures for the catalytic hydrogenation of aryl aliphatic ketones are described, for example, in US Patent Application Publication No. 2020 / 0339748 (A1) (see paragraphs
[0265] -
[0270] of US Patent Application Publication No. 2020 / 0339748 (A1)), which can be similarly applied in the processes of this specification. In this preferred protocol, the reaction is carried out without a solvent, and less than stoichiometric amounts of an alkali (e.g., NaOH) are used as an additive to enhance the hydrogenation selectivity for the desired benzyl alcohol derivative.
[0159] Those skilled in the art can, taking into account their common general knowledge, modify the aryl aliphatic ketone hydrogenation procedures applied in the art for the purposes of the present invention, if necessary.
[0160] Step c of Option a: Then, the secondary alcohol of formula V: Ar-CH(OH)-CH2-R3, wherein Ar and R3 are as defined above and in the claims, obtained from step b, is subjected to a sulfation step with a sulfating agent, followed by neutralization with a base XOH or X(OH2), whereby R1 is OSO3X, X is as defined above and in the claims, R2 is H, and R3 is C2-C 26 To obtain a compound of formula I which is an aliphatic group.
[0161] The sulfation of secondary alcohols is a standard reaction that forms part of the common general knowledge of those skilled in the art.
[0162] In connection with this process, the sulfation of the secondary alcohol of formula V: Ar-CH(OH)-CH2-R3 (V) can be carried out using known sulfating agents. Sulfating agents useful in the present invention are selected, for example, from the group consisting of SO3, chlorosulfonic acid (ClSO3H), fuming sulfuric acid, and sulfamic acid (H3NSO3). Preferably, SO3 or chlorosulfonic acid (ClSO3H) is used as the sulfating agent in the process of the present invention.
[0163] Sulfation can be carried out in solution. Those skilled in the art can select a suitable solvent from the range of standard solvents widely used in organic synthesis, including but not limited to, for example, CH2Cl2, CHCl3, CCl4, pyridine, ethyl acetate, dioxane, diglyme, THF, 2-methyl-THF, hydrocarbons, or mixtures thereof, taking into account their common general knowledge.
[0164] Alternatively, sulfation can be carried out without a solvent when the alcohol is in a molten state.
[0165] The sulfation step can be carried out at a temperature in the range of -20 °C to 120 °C, preferably 0 °C to 80 °C. Due to the exothermic nature of the reaction, the sulfating agent is typically added to the substrate at a lower temperature (e.g., within the range of -20 °C to 10 °C). Subsequently, the temperature is typically increased to accelerate the reaction and increase the conversion rate. When SO3 is used as the sulfating agent, sulfation can be carried out using, for example, a so-called falling film reactor, with gaseous SO3 diluted in dry air or dry nitrogen (e.g., 1 - 5% v / v).
[0166] Those skilled in the art can control the progress of the sulfation reaction using standard techniques such as NMR, taking into account their common general knowledge.
[0167] The aging step may optionally be included after the sulfation step to achieve complete conversion to the sulfonic acid. Such an aging step can be carried out, for example, at a temperature of 15 °C to 200 °C.
[0168] After the sulfation step, a neutralization step follows to complete the salt formation of the desired product, i.e., the compound of formula (I).
[0169] Neutralization can be carried out using a base compound of the general formula XOH or X(OH)2, where X is an alkali metal, alkaline earth metal, or ammonium group as defined above. X can be, for example, Li, Na, K, Cs, NH4, triethanolammonium, Mg, or Ca.
[0170] Neutralization using a basic compound of the general formula XOH or X(OH)2 is typically carried out in an aqueous solution (or in a solvent mixture to which an aqueous solution of the basic compound of the general formula XOH or X(OH)2 is added). The neutralization is typically carried out at a temperature in the range of 0 °C to 100 °C, preferably at a temperature in the range of 0 °C to room temperature. "Room temperature" for the purposes of this process is defined herein as in the range of 20 °C to 30 °C.
[0171] Those skilled in the art can, taking into account their common general knowledge, use common purification and separation techniques such as distillation methods, precipitation / crystallization methods (where applicable), and chromatography methods (including, for example, flash chromatography and HPLC) to purify the product mixture obtained from the sulfation and subsequent neutralization steps.
[0172] Those skilled in the art can, taking into account their common general knowledge, modify the sulfation procedure applied in the art for the purposes of the process if necessary.
[0173] Option b: Steps b and c - Sulfonation - Hydrogenation - Neutralization The sulfonation - hydrogenation sequence according to steps b and c of option b of this process is further described below.
[0174] Step b of option b: In the process according to option b, the aryl - aliphatic ketone of formula IV: Ar - C(=O) - CH2 - R3 (IV) obtained from the decarboxylation cross - ketonization step is sulfonated with a sulfonating agent and subsequently neutralized with a base XOH or X(OH)2, thereby obtaining an aryl - aliphatic ketone sulfonate of formula VI: Ar - C(=O) - CH(SO3X) - R3 (VI), wherein Ar, X, and R3 are as defined above and in the claims.
[0175] The sulfonation of aryl aliphatic ketones using a sulfonating agent is known to those skilled in the art and is described, for example, in WO 2018 / 229285 (A1) (see page 43, lines 5 to 22). Step b of option b in this process can be carried out according to the above-known procedure described in WO 2018 / 229285 (A1).
[0176] According to the known procedure from WO 2018 / 229285 (A1), the sulfonation step in this process can be carried out, for example, preferably using gaseous SO3 diluted (e.g., 1 to 5% v / v) in dry air or dry nitrogen as the sulfonating agent. In this case, the sulfonation using diluted SO3 can be carried out using a so-called falling film reactor. Other sulfonating agents useful herein include chlorosulfonic acid (ClSO3H), fuming sulfuric acid, and sulfamic acid (H3NSO3). Preferably, SO3 or chlorosulfonic acid (ClSO3H) is used as the sulfonating agent.
[0177] The reaction is typically carried out at a temperature in the range of -20 °C to 200 °C, preferably in the range of 0 °C to 120 °C. Due to the exothermic nature of the reaction, the sulfonating agent is typically added to the substrate at a lower temperature (e.g., within the range of -20 °C to 10 °C). After the addition is complete, the temperature is typically raised to accelerate the reaction and increase the conversion rate.
[0178] The sulfonation can be carried out in solution or neat. Those skilled in the art can select a suitable solvent from the range of standard solvents widely used in organic synthesis, including but not limited to CH2Cl2, CHCl3, CCl4, pyridine, ethyl acetate, dioxane, diglyme, THF, 2-methyl-THF, hydrocarbons, or mixtures thereof, taking into account their common general knowledge.
[0179] Those skilled in the art can control the progress of the sulfonation reaction using standard techniques such as NMR, taking into account their common general knowledge.
[0180] The aging step may optionally be included after the sulfonation step in order to achieve complete conversion to the sulfonic acid. Such an aging step can be carried out, for example, at a temperature of 15°C to 200°C.
[0181] Following the sulfonation step, a neutralization step is carried out to complete the salt formation of the desired product, namely the arylaliphatic ketone sulfonate of formula VI: Ar-C(=O)-CH(SO3X)-R3 (VI).
[0182] Neutralization can be carried out as already described in connection with step c of alternative a of the process according to the invention.
[0183] Those skilled in the art can use common purification and separation techniques such as distillation methods, precipitation / crystallization methods (where applicable), and chromatography methods (including, for example, flash chromatography and HPLC) to purify the product mixture obtained from the sulfonation and subsequent neutralization steps, taking into account their common general knowledge.
[0184] Those skilled in the art can also modify the sulfonation procedures applied in the art for the purposes of the present invention, taking into account their common general knowledge, if necessary.
[0185] Step c of alternative b: The arylaliphatic ketone sulfonate of formula VI: Ar-C(=O)-CH(SO3X)-R3 (VI) [wherein Ar, X and R3 are as defined above and in the claims] is then subjected to a hydrogenation step in the presence of H2 and a catalyst, whereby a first compound of formula I [wherein R1 is OH, R2 is SO3X, X is as defined above, and R3 is a C6-C 16 aliphatic group]; or a second compound of formula I wherein R1 is H, R2 is SO3X, X is as defined above and in the claims, and R3 is a C6-C16 aliphatic group; or a mixture of the first compound and the second compound of formula I can be obtained.
[0186] The catalytic hydrogenation of arylaliphatic ketones to obtain the corresponding arylaliphatic alcohols is a standard reaction generally known to those skilled in the art.
[0187] In the context of step c of option b, the catalytic hydrogenation can be carried out in the same manner as described above in relation to step b of option a of the present process.
[0188] Those skilled in the art can also adjust the hydrogenation conditions, taking into account their common general knowledge, to obtain the first compound of formula I and reduce the amount of the second compound of formula I formed, or to obtain the second compound of formula I and reduce the amount of the first compound of formula I. Those skilled in the art can control the progress of the reaction using standard techniques such as NMR, taking into account their common general knowledge.
[0189] Furthermore, those skilled in the art can purify the product mixture obtained from the hydrogenation step using common purification and separation techniques such as distillation, precipitation / crystallization methods (where applicable), and chromatography methods (including, for example, flash chromatography and HPLC), taking into account their common general knowledge.
[0190] Combination 1. A fabric and home care product comprising a surfactant of formula I,
[0191]
Chemical formula
[0192] The dimensions and values disclosed herein are not to be understood as being strictly limited to the exact numerical values recited. Instead, unless otherwise indicated, each such dimension is intended to mean both the recited value and the functionally equivalent range surrounding that value. For example, a dimension disclosed as "40 mm" is intended to mean "about 40 mm".
[0193] All documents cited herein, including any patents or patent applications that are cross - referenced or related, and any patent application or patent for which this application claims priority or the benefit thereof, are incorporated herein by reference in their entirety, unless expressly excluded or limited. The citation of any document is not to be construed as an admission that it is prior art to any invention disclosed or claimed herein, nor that it alone, or in any combination with any other one or more references, teaches, suggests, or discloses any such invention. Further, any meaning or definition of a term in this document that conflicts with any meaning or definition of the same term in a document incorporated by reference shall be determined by the meaning or definition given to the term in this document.
[0194] Although specific embodiments of the invention have been illustrated and described, it will be apparent to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. Accordingly, it is intended that all such changes and modifications within the scope of the invention be covered by the appended claims.
Claims
1. A fabric and a home care product containing a surfactant of formula I, 【Chemical 1】 wherein Ar represents an aryl group, R 1 is a group of H or OR, wherein R is H or SO 3 X, wherein X is an alkali metal, an alkaline earth metal or an ammonium of the general formula R'R''R'''R'''', wherein R', R'', R''' and R'''' are independently selected from hydrocarbyl groups which may be optionally substituted and / or interrupted by one or more heteroatom-containing groups, R 2 is H or SO 3 X, where X is an alkali metal, an alkaline earth metal or an ammonium of the general formula R'R''R'''R'''', where R', R'', R''' and R'''' are independently selected from hydrocarbyl groups which may be optionally substituted and / or interrupted by one or more heteroatom-containing groups, and provided that, wherein, R 1 and R 2 are different groups, R 2 is SO 3 X, when R 1 is H or OR, and R is H R 2 When R is H, 1 R is OR and R is SO 3 X, R 3 is a C 6 -C 16 aliphatic group, fabric and home care products.
2. The fabric and home care product according to claim 1, wherein Ar is a phenyl group.
3. The fabric and home care product according to claim 1 or 2, wherein X is sodium.
4. R 1 is OSO 3 with X, R 2 The fabric and home care product according to any one of claims 1 to 3, wherein R is H.
5. R 1 is OH, and R 2 is SO 3 X, the fabric and home care product according to any one of claims 1 to 3.
6. R 1 is H, R 2 is SO 3 X, the fabric and home care product according to any one of claims 1 to 3.
7. R 3 is an aliphatic group from C 10 to C 16 The fabric and home care product according to any one of claims 1 to 6, wherein
8. R 3 is a C 14 -C 16 aliphatic group, the fabric and home care product according to any one of claims 1 to 6.
9. The fabric and home care product according to any one of claims 1 to 8, wherein the product is a hard surface cleaner, a laundry detergent, a fragrance, a dishwashing detergent, a fabric conditioner, a hard surface cleaner, a laundry additive, a rinse additive, or a combination thereof.
10. The fabric and home care product according to any one of claims 1 to 9, wherein the product contains 5% to 65% by weight of the surfactant.
Citation Information
Patent Citations
No title available
GB1239720A
Aromatic compound and method for preparing the same
JP2001097943A
Composition containing a mixture of C10-C13 alkylphenyl sulfonates
JP2014511407A