EP4634358A1 - Solid laundry composition - Google Patents
Solid laundry compositionInfo
- Publication number
- EP4634358A1 EP4634358A1 EP23821290.6A EP23821290A EP4634358A1 EP 4634358 A1 EP4634358 A1 EP 4634358A1 EP 23821290 A EP23821290 A EP 23821290A EP 4634358 A1 EP4634358 A1 EP 4634358A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- water
- fatty acid
- composition according
- fabric conditioning
- conditioning composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0047—Detergents in the form of bars or tablets
- C11D17/0052—Cast detergent compositions
-
- 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
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
-
- 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
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
-
- 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
Definitions
- Solid fabric conditioners provide consumers with an easy-to-use concentrated fabric conditioner 10 composition. These compositions have various benefits including that they can contain high levels of active ingredient and have very low water content, leading to easier storage and transportation.
- Solid fabric conditioners come in different shapes and sizes, for example tablets, sheets, 15 shaped articles, etc. the ‘stickiness’ or lack of ‘stickiness’ is an important physical characteristic of a solid fabric conditioner. A sticky product may stick to other articles, is not easy for a consumer handle and could potentially leave residues on the consumers hands.
- a solid fabric conditioning 25 composition comprising: a Ester linked quaternary ammonium compound fabric softening active; b 0.1 to 3 wt.% fatty acid amide having a fatty acid chain length of 12 or more carbons; and 30 c 5 to 70 wt.% Water soluble carrier selected form polysaccharides.
- the invention further relates to a method of preparing a solid fabric conditioning composition
- a method of preparing a solid fabric conditioning composition comprising the steps of; 35 a Preparing a premix of the water-soluble carrier and water; P0000150 CPL 2 b Adding the fabric softening active, 0.1 to 3 wt.% fatty acid amide having a fatty acid chain length of 12 or more carbons and any remaining ingredients to the premix; c Casting the mixture on a surface or in a mold; and d Removing the water, preferably by evaporation.
- any feature of one aspect of the present invention may be utilised in any other aspect of the invention.
- the word “comprising” is intended to mean “including” but not necessarily “consisting of” or “composed of.” In other words, the listed steps or options need not be exhaustive. It is noted that the examples given in the description below are intended to clarify the invention and are not intended to limit the invention to those examples per se. 15 Similarly, all percentages are weight/weight percentages unless otherwise indicated. Except in the operating and comparative examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material or conditions of reaction, physical properties of materials and/or use are to be understood as modified by the word “about”.
- compositions described herein comprise ester-linked quaternary ammonium fabric softening active.
- the quaternary ammonium compound (QAC) preferably comprises at least one chain derived 30 from fatty acids, more preferably at least two chains derived from a fatty acid. Generally fatty acids are defined as aliphatic monocarboxylic acids having a chain of 4 to 28 carbons.
- Fatty acids may be derived from various sources such as tallow or plant sources.
- the fatty acid chains are derived from plants.
- the fatty acid chains of the QAC comprise from 10 to 50 wt. % of saturated C18 chains and from 5 to 40 wt. % of monounsaturated C18 chains 35 by weight of total fatty acid chains.
- the fatty acid chains of P0000150 CPL 3 the QAC comprise from 20 to 40 wt. %, preferably from 25 to 35 wt. % of saturated C18 chains and from 10 to 35 wt. %, preferably from 15 to 30 wt. % of monounsaturated C18 chains, by weight of total fatty acid chains.
- the quaternary ammonium fabric softening actives for use in compositions described herein are so called "ester quats" or ester-linked quaternary ammonium compounds.
- Particularly preferred materials are the ester-linked triethanolamine (TEA) quaternary ammonium compounds comprising a mixture of mono-, di- and tri-ester linked components.
- TAA triethanolamine
- TEA-based fabric softening compounds comprise a mixture of mono, di- and tri ester forms of the compound where the di-ester linked component comprises no more than 70 wt.% of the fabric softening compound, preferably no more than 60 wt.% e.g., no more than 55%, or even no more that 45% of the fabric softening compound and at least 10 wt.% of the monoester linked component.
- a first group of quaternary ammonium compounds (QACs) suitable for use in the compositions are represented by formula (I): wherein each R is independently selected from a C5 to C35 alkyl or alkenyl group; R 1 20 represents a C1 to C4 alkyl, C2 to C4 alkenyl or a C1 to C4 hydroxyalkyl group; T may be either O-CO. (i.e. an ester group bound to R via its carbon atom), or may alternatively be CO-O (i.e.
- a second group of QACs suitable for use in the compositions described herein is represented by formula (II): P0000150 CPL 4 wherein each R 1 group is independently selected from C1 to C4 alkyl, hydroxyalkyl or C2 to C4 alkenyl groups; and wherein each R 2 group is independently selected from C8 to C28 alkyl or alkenyl groups; and wherein n, T, and X- are as defined above.
- Preferred materials of this second group include 1,2 bis[tallowoyloxy]-3- trimethylammonium propane chloride, 1,2 bis[hardened tallowoyloxy]-3- trimethylammonium propane chloride, 1,2- bis[oleoyloxy]-3-trimethylammonium propane chloride, and 1,2 bis[stearoyloxy]-3- trimethylammonium propane chloride.
- Such materials are described in US 4, 137,180 (Lever10 Brothers).
- these materials also comprise an amount of the corresponding mono- ester.
- a third group of QACs suitable for use in the composition are represented by formula (III): 15 wherein each R 1 group is independently selected from C1 to C4 alkyl, or C2 to C4 alkenyl groups; and wherein each R 2 group is independently selected from C8 to C28 alkyl or alkenyl groups; and n, T, and X- are as defined above.
- Preferred materials of this third group include 20 bis(2-tallowoyloxyethyl)dimethyl ammonium chloride, partially hardened and hardened versions thereof.
- a particular example of the fourth group of QACs is represented the by the formula (IV): 5
- a fifth group of QACs suitable for use in the composition are represented by formula (V)
- R 1 and R 2 are independently selected from C10 to C22 alkyl or alkenyl groups, preferably C14 to C20 alkyl or alkenyl groups.
- X- is as defined above.
- the iodine value of the quaternary ammonium fabric conditioning material is preferably from 0 to 80, more preferably from 0 to 60, and most preferably from 0 to 45. The iodine value may be chosen as appropriate.
- Essentially saturated material having an iodine value of from 0 to 5, preferably from 0 to 1 may be used in the compositions described herein. Such materials are 15 known as “hardened” quaternary ammonium compounds. A further preferred range of iodine values is from 20 to 60, preferably 25 to 50, more preferably from 30 to 45. A material of this type is a "soft" triethanolamine quaternary ammonium compound, preferably triethanolamine di-alkylester methylsulfate. Such ester-linked 20 triethanolamine quaternary ammonium compounds comprise unsaturated fatty chains.
- the iodine value represents the mean iodine value of the parent fatty acyl compounds or fatty acids of all the quaternary ammonium materials present.
- the iodine value 25 represents the mean iodine value of the parent acyl compounds of fatty acids of all of the quaternary ammonium materials present.
- the fabric softening active comprises a mixture of cationic quaternary ammonium compound having more than one long carbon chain in combination with a secondary surfactant selected from a single chain cationic surfactant and/or a non-ionic surfactant.
- the cationic quaternary ammonium compound having more than one long 10 carbon chain and secondary surfactant are present in a ratio of 1:10 to 10:1, more preferably 1:5 to 5:1.
- the combination of the cationic quaternary ammonium compound having more than one long carbon chain in combination with a secondary surfactant selected from a single chain cationic surfactant and/or a non-ionic surfactant provide a solid composition which can be diluted with water to form a stable liquid fabric softener and provides superior softening.
- 15 Cationic quaternary ammonium compound having more than one long carbon chain are as described above.
- Suitable single chain cationic surfactant preferably have the general formula: 20 (R 1 ) 3 – N + - R 2 X- Wherein each R 1 independently comprises 1 to 6 carbon atoms, selected from alky, alkenyl, aryl or combinations thereof. Each R 1 may independently comprise hydroxy groups. Preferably at least two of the R 1 groups correspond to a methyl group. 25 Wherein R 2 comprises at least 10 carbon atoms. The carbon atoms may be in the form of an alky, alkenyl, aryl or combinations thereof.
- the single chain cationic surfactant comprises at least 12 carbon atoms, preferably at least 14 and most preferably at least 16. R 2 may further comprise additional functional groups such as ester groups or hydroxy groups.
- compositions described herein comprise more than 5 wt. % fabric softening active, more preferably more than 10 wt. % fabric softening active, most preferably more than 20 wt.
- the fabric conditioners of the described herein comprise less than 80 wt. % fabric softening active, more preferably 5 less than 70 wt. % fabric softening active, most preferably less than 65 wt. % fabric softening active by weight of the composition.
- the fabric conditioners comprise 5 to 80 wt. % fabric softening active, preferably 10 to 70 wt.% fabric softening active and more preferably 20 to 65 wt. % fabric softening active by weight of the composition.
- the solid fabric conditioning composition comprises fatty acid amide having a fatty acid chain length of 12 or more carbons.
- the fatty acid amide has a fatty acid carbon chain of less than 40. More preferably the fatty acid chain is 14 to 30 carbons long, even more preferably 16 to 26. 15
- the fatty acid chain may be fully saturated, mono or poly unsaturated.
- the fatty acid chain may be substituted and/or may be branched.
- the fatty acid chain is unsubstituted,
- the fatty acid chain is a straight chain (unbranched).
- the compositions comprise 0.1 to 3 wt.% fatty acid amide having a fatty acid chain length of 12 or more carbons by weight of the composition. Preferably 0.5 to 2.8 wt.
- Water soluble carrier examples include: starch, xanthan gum, carboxymethyl cellulose.
- the water-soluble carrier is selected from polysaccharides, more preferably cellulose derivatives. Most preferably cellulose ether derivatives. Typically, cellulose ether derivatives are30 obtained by substituting one or more hydrogen atoms of hydroxyl groups in the anhydro- glucose units of cellulose with alkyl or substituted alkyl groups. Degree of substitution (DS) is one of the factors, that define the properties of cellulose ether derivatives, particularly, solubility in water.
- cellulose ether derivatives with degree of 35 substitution values between 1.2 to 2.4 are soluble in cold water.
- examples of cellulose ether P0000150 CPL 8 derivatives suitable for the compositions described herein includes methyl cellulose (MC), hydroxyethyl cellulose (HEC), hydroxypropyl cellulose (HPC), hydroxypropyl methyl cellulose (HPMC), carboxymethyl cellulose (CMC) and sodium carboxymethyl cellulose (SCMC).
- MC methyl cellulose
- HEC hydroxyethyl cellulose
- HPC hydroxypropyl cellulose
- HPMC hydroxypropyl methyl cellulose
- SCMC sodium carboxymethyl cellulose
- the cellulose ether derivative is selected form hydroxypropyl methyl cellulose, methyl 5 cellulose, hydroxypropyl cellulose, and combinations thereof.
- Most preferred cellulose ether derivative is hydroxypropyl methyl cellulose.
- the compositions described herein 5 to 70 wt.%, more preferably 7.5 to 50 wt.% and most preferably 10 to 40 wt.% water-soluble carrier materials, by weight of the composition.
- the water-soluble carrier preferably has a solubility at least 0.5% by weight in distilled water at 25 °C.
- a solubility at least 1.0 % by weight, more preferably at least 2 % by weight, and most preferably at least 3% by weight in distilled water at 25 °C.
- a solubility of at least 5 mg/ml of distilled water at 25°C preferably at least 10 mg/ml of distilled water at 25°C, more preferably at least 20 mg/ml of distilled water at 25°C, most preferably 30 mg/ml of 15 distilled water at 25°C.
- Swellable disintegrant The compositions described herein preferably comprise a swellable disintegrant. Swellable disintegrant herein refers to the components which swell in contact with water. The swellable 20 disintegrant acts synergistically with the fatty acid amide to improve dissolution time and stickiness.
- the swellable disintegrant has a Water Absorption Ratio (WAR) of greater than 1, more preferably greater than 1.5.
- WAR Water Absorption Ratio
- WAR Water Absorption Ratio
- the process described in ASTM D570 is suitable for measuring water absorption ratios.
- the water absorption may be measured by: - Procuring a dry sample of the material to be tested P0000150 CPL 9 - Weighing the sample to be tested then, placing in a container of boiling distilled water for 120 minutes, ensuing it is entirely immersed - Removing the specimen and removing excess water with filter paper.
- the swellable disintegrant is preferably selected from sodium croscarmellose, sodium starch glycollate, crospovidone, C-TAG (co grinded treated agar) and C-TGG (co grinded treated guar gum), mucilage (for example from Isapgula or Fenugreek seed), Chitin, cross-linked cellulose 10 (for example microcrystalline cellulose), sodium starch glycolate and mixtures thereof. More preferably the swellable disintegrant is selected from crosslinked cellulose (preferably microcrystalline cellulose), sodium starch glycolate and mixtures thereof.
- the water swellable disintegrant is selected from crosslinked cellulose, and most preferably the water swellable disintegrant is selected from microcrystalline cellulose. 15
- the composition may comprise from 1 to 30% by weight swellable disintegrant, more preferably from 2 to 20% by weight and most preferably from 3 to 15% by weight swellable disintegrant.
- the composition described herein may further comprise a non-swellable disintegrant.
- Non- swellable disintegrant herein refer to those which have water absorption ratio (WAR) less than 1.
- WAR water absorption ratio
- the non-swellable disintegrate is selected from polyvinyl pyrrolidone, calcium 20 silicate, starch, magnesium stearate and mixtures thereof.
- Carbonaceous material The compositions described herein preferably comprise carbonaceous materials.
- the carbonaceous material leads to improved strength of the solid composition.
- Carbonaceous 25 materials refer to materials having a 2D carbon lattice nanostructure.
- the 2D lattice may be flat for example graphene or may be shaped into a 3D shape such as carbon nanotubes.
- the carbonaceous material may be part of a larger structure, such as a composite material e.g. clay-carbonaceous material composite.
- the carbonaceous materials comprise a material selected from carbon nanotubes, graphene, activated carbon and combinations 30 thereof. More preferably the carbonaceous materials comprise preferably graphene and/or derivatives thereof and most preferably graphene oxide.
- Graphene is an allotrope, formed by a single layer carbon atoms arranged in hexagonal lattice structure. Graphene can be obtained in two manners. The first is by peeling layers from graphite until you achieve a graphene monolayer. The second is known as Chemical Vapor Deposition (CVD) and where large-scale uniformity can be obtained and controlled. 5
- the graphene derivative suitable for the compositions described herein is graphene oxide.
- Graphene oxide can be manufactured through Hummer’s method. Graphene oxide is also commercially available and may be procured from suppliers such as Platonic Nanotech.
- compositions described herein preferably comprise 0.001 to 2 wt.% carbonaceous materials, more preferably 0.0025 to 1 wt.% carbonaceous materials, even more preferably 0.005 to 0.5 wt.% carbonaceous materials and most preferably 0.01 to 0.25 wt.% carbonaceous materials. 15 Other ingredients
- the compositions described herein may comprise additional ingredients common in the field of solid fabric conditioners, for example perfumes, perfume microcapsules, dyes, antifoams, insect repellents, shading or hueing dyes, preservatives (e.g.
- compositions described herein may contain pearlisers and/or opacifiers.
- the compositions comprise perfume, more preferably comprises 0.1 to 25 wt.% 25 perfume, even more preferably 1 to 20 wt. % perfume and most preferably 2 to 15 wt.% perfume.
- Water The solid fabric conditioner described herein are preferably ‘free from water’ when 30 manufactured, however they may absorb moisture on storage.
- the composition comprises 0 to 20 wt.% weight, more preferably 0 to 15 wt.% water, most preferably 0 to 12 wt.% water.
- Water content may be measured by thermogravimetry, like moisture balance. 35 P0000150 CPL 11 Process of making and use of the compositions
- the solid fabric conditioner composition described herein may be in any suitable form.
- a single dose of the composition may be a single article (e.g. a tablet or sheet), a part of a single article (i.e. a part of a sheet separated by tearing a section off a larger sheet), or may consist of 5 multiple articles, (e.g. multiple particles of the composition).
- the solid composition is in the form of articles having a minimum linear dimension in any direction of more than 1 mm.
- the solid fabric conditioner composition does not include powders.
- the solid composition is in a form suitable for use as a single article for example a tablet or sheet. These may be referred to as a ‘unit dose’. 10
- the solid fabric conditioner may be made by any suitable process.
- a preferred method comprises the steps of; a) Preparing a premix of a water-soluble carrier and water; 15 b) Adding fabric softening active, 0.1 to 3 wt.% fatty acid amide having a fatty acid chain length of 12 or more carbons and any remaining ingredients to the premix; c) Casting the mixture on a surface or in a mold; and d) Removing the water, preferably by evaporation.
- Step a) preferably comprises mixing and/or heating.
- Step b) preferably comprises mixing fabric softening active, 0.1 to 3 wt.% fatty acid amide having a fatty acid chain length of 12 or more carbons and any remaining ingredients with water prior to addition to the pre-mix.
- step c) if casting is used, preferably the thickness is controlled using an applicator.
- the mixture is preferably cast onto a Polytetrafluoroethylene (PTFE) surface, for example PTFE sheets, PTFE coated foils or PTFE coated fabrics.
- Step d) preferably takes place at a temperature above room temperature (above 25°C), preferably at less than 100 °C, and more preferably less than 95 °C. Most preferably water is removed at a temperature of 70 to 90 °C.
- Preferably water is removed to reach a composition water content of 0 to 20 wt.%, more preferably a water content of 0 to 15 wt.%, more preferably 0 to 10 wt.%, even more preferably 0 to 5 wt. % and most preferably 0 to 2 wt.%.
- P0000150 CPL 12 More specifically a homogenized premix of water and water-soluble carrier is prepared with mixing. Subsequently, fabric softening active, 0.1 to 3 wt.% fatty acid amide having a fatty acid chain length of 12 or more carbons and any remaining ingredients are mixed with water under high shear before being added to the premix.
- Keval Exports The formulations where prepared by dispersing the hydroxypropyl methyl cellulose in hot water 15 to make a 10% polymer solution. Separately the quaternary ammonium compound and perfume were mixed in the remaining water under high shear to make an emulsion. The remaining ingredients were added to the emulsion and mixed. The final mix was added to the polymer solution at room temperature and mixed well at high shear until a stable foam was formed. The foam was cast on a smooth, hard surface and dried at 80-90 o C for 2 hours. The dried sheet was 20 detached from the substrate on cooling. P0000150 CPL 13 Dissolution time was measured the following method.300 ml of water was placed in a 500ml beaker at room temperature.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Emergency Medicine (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP22213631 | 2022-12-14 | ||
| PCT/EP2023/084985 WO2024126308A1 (en) | 2022-12-14 | 2023-12-08 | Solid laundry composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP4634358A1 true EP4634358A1 (en) | 2025-10-22 |
Family
ID=84535866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP23821290.6A Pending EP4634358A1 (en) | 2022-12-14 | 2023-12-08 | Solid laundry composition |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP4634358A1 (en) |
| CN (1) | CN120303386A (en) |
| WO (1) | WO2024126308A1 (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1567947A (en) | 1976-07-02 | 1980-05-21 | Unilever Ltd | Esters of quaternised amino-alcohols for treating fabrics |
| GB8609884D0 (en) * | 1986-04-23 | 1986-05-29 | Procter & Gamble | Softening detergent compositions |
| US4938879A (en) * | 1989-04-04 | 1990-07-03 | Creative Products Resource Associates, Ltd. | Stearate-based dryer-added fabric softener sheet |
| WO2008040151A1 (en) * | 2006-09-01 | 2008-04-10 | Tao Wang | Synthetic detergent and its preparation method |
| CN110184806A (en) * | 2019-06-23 | 2019-08-30 | 无锡华鑫检测技术有限公司 | A kind of graphene-based wool softening agent and preparation method thereof |
| AU2021263558B2 (en) * | 2020-04-29 | 2026-02-26 | Stepan Company | Solid compositions containing amine, protonated amine or quaternary ammonium compounds |
-
2023
- 2023-12-08 WO PCT/EP2023/084985 patent/WO2024126308A1/en not_active Ceased
- 2023-12-08 EP EP23821290.6A patent/EP4634358A1/en active Pending
- 2023-12-08 CN CN202380083734.8A patent/CN120303386A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN120303386A (en) | 2025-07-11 |
| WO2024126308A1 (en) | 2024-06-20 |
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