WO2002077063A1 - Polyesters nettoyants - Google Patents

Polyesters nettoyants Download PDF

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Publication number
WO2002077063A1
WO2002077063A1 PCT/EP2002/003467 EP0203467W WO02077063A1 WO 2002077063 A1 WO2002077063 A1 WO 2002077063A1 EP 0203467 W EP0203467 W EP 0203467W WO 02077063 A1 WO02077063 A1 WO 02077063A1
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WO
WIPO (PCT)
Prior art keywords
mol
polyester according
less
component
acid
Prior art date
Application number
PCT/EP2002/003467
Other languages
German (de)
English (en)
Inventor
Sebastian Koltzenburg
Frank Klippel
Christine MÜLLER
Bernhard Mohr
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2002077063A1 publication Critical patent/WO2002077063A1/fr

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/507—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3715—Polyesters or polycarbonates
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • the present invention relates to dirt-removing polyesters, a process for their preparation, detergents and cleaning agents containing them and their use for impregnating textiles.
  • Dirt-releasing polymers are widely used in detergents and cleaning agents for textiles. They are intended to give the textiles treated with it, in particular those made from polyester fibers, dirt-repellent properties. Polyesters which contain not only hydrophobic but also hydrophilic structural units are frequently used as dirt-removing polymers. Due to their structural relationship to polyester fibers or polyester blended fabrics, they are adsorbed onto the fabric from an aqueous solution or a washing liquor and form a hydrophilic film there. This has the effect that the affinity of the tissue for hydrophobic oil and grease dirt is reduced. At the same time, the wettability of the fabric with the aqueous washing liquor is improved. Both lead to an easier removal of oily or greasy soiling. In addition, the dirt-removing polymers also improve the antistatic and sliding properties, which makes it easier to handle the fabrics during textile processing.
  • DE 40 01 415 discloses polyesters from carboxylic acids with at least two carboxyl groups, polyhydric alcohols and water-soluble alkylene oxide adducts with long-chain alcohols, alkylphenols or alkylamines and optionally alkoxylated polyhydric alcohols.
  • the polyesters serve as graying-inhibiting and dirt-removing additives in detergents.
  • EP 964 015 describes oligoesters which by polycondensation of 40 to 52 mol% of a dicarboxylic acid, 10 to 40 mol% of ethylene glycol and / or propylene glycol, 3 to 20 mol% of polyethylene glycol, 0.5 to 10 mol% of a water-soluble Alkylene oxide adduct of an alcohol, long-chain alkylphenol or alkylamine and 0.4 to 10 mol% of a polyol with 3 to 6 hydroxyl groups can be obtained.
  • the oligoesters serve as dirt-releasing polymers in detergents.
  • the dirt-removing effect of the known polyester is not fully satisfactory.
  • the present invention is therefore based on the object of providing new dirt-removing polyesters with favorable dirt-removing properties.
  • polyester which by polycondensation of
  • the present invention also relates to detergents or cleaning agents for textiles or smooth surfaces which contain a polyester according to the invention, and the use of the polyesters according to the invention for impregnating textiles to improve the antistatic and sliding properties.
  • “Hydroxyl equivalents” is understood to mean the amount of substance in moles of a species containing hydroxyl groups, multiplied by the number of its hydroxyl groups. So corresponds to B. 1 mol of glycerol 3 mol of hydroxyl equivalents. A corresponding definition applies to "carboxyl equivalents".
  • the polyesters according to the invention preferably have an acid number of less than 5, in particular less than 3, particularly preferably less than 1.5.
  • the hydroxyl number indicates how many mg of potassium hydroxide are equivalent to the amount of acetic acid that is bound by 1 g of polyester during acety- lization. The determination is carried out in accordance with DIN 53240.
  • the acid number indicates the number of mg KOH that is used to neutralize 1 g polyester. The determination is made according to DIN 53402.
  • the hydroxyl and acid numbers reflect the proportion of the free carboxyl or hydroxy1 end groups of the polyesters. Low hydroxyl and acid numbers correspond to a high degree of condensation and thus a high molecular weight. It has been found that the dirt-removing effect of the polyesters increases sharply with increasing molecular weight, expressed by low hydroxyl or acid numbers.
  • Aliphatic or aromatic di-, tri-, tetra- or higher carboxylic acids are suitable as dibasic or higher carboxylic acid, but preferably aromatic dicarboxylic acids.
  • Suitable aliphatic dicarboxylic acids are oxalic acid, succinic acid, glutaric acid, adipic acid, fumaric acid, maleic acid and itaconic acid. They can be used as such or in the form of their C 1 -C 4 -alkyl esters, such as diethyl oxalate, diethyl succinate, ethyl glutarate, dimethyl adipate, diethyl adipate, di-n-butyl adipate, ethyl fumarate and maleic acid.
  • Suitable aromatic dicarboxylic acids are terephthalic acid, phthalic acid or isophthalic acid.
  • Suitable esters include dimethyl, diethyl, di-n-propyl, diisopropyl terephthalate, phthalate and isophthalate. Terephthalic acid and its esters are particularly preferred.
  • Butane tetracarboxylic acid, benzene tetracarboxylic acid and cyclohexane tricarboxylic acid can be cited as examples of higher quality carboxylic acids.
  • Polyalkylene oxides are the adducts of alkylene oxides with water. If mixtures of different alkylene oxides are used for their preparation, they can be contained in blocks or in a statistical distribution.
  • Particularly suitable polyalkylene glycols are polyethylene glycols and polypropylene glycols or copolymers thereof. Polyethylene glycols are preferred.
  • the polyalkylene glycols used preferably have a weight-average molecular weight of 150 to 12000, in particular 1500 to 8000.
  • polyesters of the invention contain an alkoxy l michseck a C 8 -C 2 4 alcohol, C ß -Ci ⁇ alkylphenol and / or a Cs-C 24 alkylamine having 5 to 80, 10 to 50 alkylene oxide units, preferably.
  • the alkylene oxides used are preferably ethylene oxide, propylene oxide or mixtures thereof. Mixtures of ethylene oxide with propylene oxide and / or are also suitable
  • butylene oxide mixtures of ethylene oxide, propylene oxide and / or isobutylene oxide. If mixtures of different alkylene oxides are used for their preparation, the alkylene oxides can be contained in blocks or in a statistical distribution.
  • Suitable alcohols which are alkoxylated are preferably aliphatic linear saturated alcohols having 8 to 24, in particular 12 to 18, carbon atoms, such as, for example, octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol or stearyl alcohol. Also suitable are oxo alcohols which can be obtained by hydroformylation and subsequent hydrogenation of olefins, in particular octenes or dodecenes. Of the alkylphenols, octylphenol, nonylphenol and dodecylphenol are particularly important. C 2 -C 8 monoalkylamines are particularly suitable as alkylamines.
  • polystyrene resin examples include pentaerythritol, trimethylolethane, trimethylolpropane, 1,2,3-hexanetriol, sorbitol, mannitol and glycerol. Glycerin is particularly preferred.
  • the dirt-removing polyesters according to the invention are prepared by processes known per se, by adding components a), b), c), d) and e), preferably with the addition of an esterification catalyst, by distilling off water and / or volatile alcohols to a temperature of at least 120 ° C, usually 150 to 300 ° C, especially 150 to 250 ° C, heated.
  • Components a) to e) are usually first heated at atmospheric pressure, preferably under inert gases such as nitrogen, and the majority of the water and / or C 1 -C 4 -alkanol is distilled off. Then the reaction is carried out under reduced pressure, e.g. B. at less than 400 mbar, in particular less than 200 mbar, particularly preferably less than 100 mbar, while distilling off the remaining water and / or volatile alcohols.
  • the volatile alcohols are excess dihydric alcohol and / or excess
  • the heating and distillation is continued until the polyester obtained as the reaction product has a hydroxyl number of less than 65, preferably less than 55, in particular less than 50 and particularly preferably less than 45.
  • the progress of the reaction can be monitored by periodic sampling and determination of the hydroxyl number of the sample.
  • the melt viscosity increases with increasing reaction time or increasing degree of condensation.
  • esterification catalysts include zinc acetate, mixtures of calcium acetate and antimony oxide, tetraalkoxy titanates such as titanium tetraisobutanolate or titanium tetraisopropanolate, alkyltin compounds, especially alkyltin oxides such as dibutyltin oxide or monobutyltin oxide hydroxide hydrate (Fascat types) from 5 Elf-Atochem.
  • the catalysts are generally used in an amount of 20 to 5000, preferably 50 to 2000 ppm, based on the components a) to e) used.
  • the condensation can be carried out in the presence of antioxidants, e.g. B. of substituted phenols, such as 2, 5-di-tert-butylphenol, 2-methylcyclohexyl-4, 6-dimethylphenol, 2,6-di-tert-butyl-4-methylphenol, pyrogallol, phosphorous acid or others commonly used antioxidants.
  • antioxidants e.g. B. of substituted phenols, such as 2, 5-di-tert-butylphenol, 2-methylcyclohexyl-4, 6-dimethylphenol, 2,6-di-tert-butyl-4-methylphenol, pyrogallol, phosphorous acid or others commonly used antioxidants.
  • Another object of the invention are washing and cleaning agents for textiles or smooth surfaces which contain a polyester according to the invention.
  • the detergent and cleaning agent formulations can be powder, granule, paste, gel or liquid, or they can be in the form of solid washing pieces. They generally contain at least 0.1% by weight, preferably between 0.1 and 10% by weight and in particular 0.2 to 3% by weight of the polyesters according to the invention.
  • cleaning agents contain conventional ingredients, such as, in particular, surfactants, builders, bleaching agents, enzymes, and the like.
  • the washing or cleaning agents usually contain 1 to 45% by weight, preferably 5 to 80% by weight, of surfactants.
  • the surfactants used can be anionic, nonionic, amphoteric or cationic.
  • Alkyl ester sulfonates include linear esters of C 8 -C 2 o-carboxylic acids, ie fatty acids which have been sulfonated with gaseous sulfur trioxide, as described in "The Journal of the American Oil Chemists Society” 52 (1975), pp. 323-329 is.
  • Suitable starting materials are natural fats, such as tallow, coconut oil and palm oil.
  • Alkyl sulfates are the salts of C 1 -C 24 -monoalkyl esters of sulfuric acid. They are usually in the form of alkali metal, ammonium, alkylammonium or alkanolammonium salts.
  • Alkyl ether sulfates are the salts of sulfuric acid half-esters of alkoxylated C 1 -C 24 -alcohols, which usually contain 0.5 to 6, particularly preferably 0.5 to 3, alkylene oxide, preferably ethylene oxide or propylene oxide units.
  • the nonionic surfactants are polyethylene, polypropylene and polybutylene oxide condensates of alkylphenol or aliphatic alcohols; Condensation products of ethylene oxide with a reaction product of propylene oxide and ethylenediamine, as well as ethylene oxide, propylene oxide block copolymers.
  • amphoteric surfactants are alkyl betaines, alkylamide betaines, aminopropionates, aminoglycinates or amphoteric imidazolium compounds.
  • Preferred examples are cocoamphocarboxypropionate, cocoamidocarboxypropionic acid, cocoamphocarboxyglycinate and cocoamphoacetate.
  • Suitable cationic surfactants are substituted or unsubstituted, straight-chain or branched quaternary ammonium salts.
  • Inorganic builders include, for example, alkali, ammonium and alkanolammonium salts of polyphosphates such as tripolyphosphate, pyrophosphate and glassy polymeric metaphosphates, phosphonates, silicates, carbonates, including bicarbonates and sesquicarbonates, and aluminosilicates.
  • Aluminum silicate builders are particularly preferred. They can be crystalline or amorphous in structure. Preferred synthetic crystalline aluminosilicates are available under the names Zeolite A, Zeolite P (B) and Zeolite X.
  • Suitable organic builders are polycarboxyl compounds, such as ether polycarboxylates and oxydisuccinates.
  • Other suitable scaffolds are ether hydroxypolycarboxylates, copolymers of maleic anhydride with ethylene or inyl methyl ether, 1,3,5-trihydroxybenzene-2,4,6-trisulfonic acid and carboxymethyloxysuccinic acid, salts of polyacetic acids, such as, for. B. ethylenediaminetetraacetic acid and nitrilotriacetic acid, and polycarboxylic acids such as mellitic acid, succinic acid, polymaleic acid, benzene-1, 3,5-tricarboxylic acid and the like.
  • the detergents or cleaning agents can contain other customary ingredients, such as enzymes, in particular proteases, lipases and cellulases, foam boosters, foam brakes, tarnishing and / or corrosion inhibitors, suspending agents, dyes, fillers, optical brighteners, disinfectants, alkalis, hydro trope Compounds, antioxidants, enzyme stabilizers, perfumes, solvents, solubilizers, dispersants, color transfer inhibitors, eg. B.
  • enzymes in particular proteases, lipases and cellulases
  • foam boosters foam boosters
  • foam brakes foam brakes
  • tarnishing and / or corrosion inhibitors suspending agents
  • dyes fillers, optical brighteners, disinfectants, alkalis, hydro trope Compounds, antioxidants, enzyme stabilizers, perfumes, solvents, solubilizers, dispersants, color transfer inhibitors, eg. B.
  • polyamine-N-oxides such as poly- (4-vinyl-pyridine-N-oxide), polyvinylpyrrolidone, poly-N-vinyl-N-methylacetamide and copolymers of N-vinylimidazole and N-vinylpyrrolidone, processing aids, Plasticizers and antistatic agents.
  • Oxide units 43.42 kg (30.6 mol) of ethoxylated Ci ß -is fatty alcohol with 25 ethylene and 80 g Fascat 4100 (Monobutylzinnoxidhydroxid- hydrate) were placed in a 300 1 drum reactor. The reactor was flushed with nitrogen and warmed to 230 ° C. The water of reaction formed was distilled off. After 4 hours the pressure was reduced to 30 mbar. The remaining water of reaction and excess ethylene glycol were distilled off.
  • the dirt-removing effect of the samples was tested in a liquid detergent as follows: Polyester test fabric PES 854 (standard test fabric from the Krefeld laundry research institute) was washed three times with the test detergent, to which 0.75% by weight of the soil release polyester to be tested was added. The fabrics pretreated in this way were dried and soiled with used motor oil. After a contact time of 24 hours, the test cloths were washed again with the test detergent. The reflectance of the test tissue was then determined. The values were secured by repeated repetition and averaging. The photometric measurement of the reflectance in percent was measured on the Elrepho 2000 (Datacolor) at the wavelength of 460 Nm (barium primary white standard according to DIN 5033).
  • the test detergent (liquid) had the following composition: Ci 2 / Ci 4 alkylbenzenesulfonate 10.0%; C ⁇ 3 / Ci 5 tallow fatty alcohol with 7 mol of ethylene oxide
  • the control (K) contained no soil release polymer.
  • Samples 7 to 12 are characterized by a particularly good washing effect. This observation proves the critical importance of the hydroxyl number of less than 65, a further improvement is observed at a hydroxyl number of less than 50.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des polyesters nettoyants, obtenus par polyconsensation de certaines quantités d'au moins un acide carboxylique bivalent ou à valence plus élevée ou son alkylester en C1-C4, d'au moins un alcool bivalent, tel que de l'éthylèneglycol et/ou du propylèneglycol, d'un polyalkylèneglycol, d'un produit d'alcoxylation entre un alcool à chaîne longue et au moins un polyol, telle que de la glycérine, avec élimination de l'eau et des alcools volatiles par distillation jusqu'à l'obtention d'un indice d'hydroxyle inférieur à 65. Ces polyesters sont particulièrement utiles en tant qu'agents auxiliaires pour détergents et peuvent servir à améliorer les propriétés antistatiques et le glissement de textiles.
PCT/EP2002/003467 2001-03-28 2002-03-27 Polyesters nettoyants WO2002077063A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10115250.7 2001-03-28
DE2001115250 DE10115250A1 (de) 2001-03-28 2001-03-28 Schmutzablösende Polyester

Publications (1)

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WO2002077063A1 true WO2002077063A1 (fr) 2002-10-03

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011120799A1 (fr) 2010-04-01 2011-10-06 Unilever Plc Procédé de structuration de liquides détergents à l'aide d'huile de ricin hydrogénée
EP2476743A1 (fr) 2011-04-04 2012-07-18 Unilever Plc, A Company Registered In England And Wales under company no. 41424 of Unilever House Procédé de lavage du linge
EP2495300A1 (fr) 2011-03-04 2012-09-05 Unilever Plc, A Company Registered In England And Wales under company no. 41424 of Unilever House Structuration de liquides détergents avec de l'huile de ricin hydrogénée
WO2013139702A1 (fr) 2012-03-21 2013-09-26 Unilever Plc Particules de détergent à lessive
WO2014130257A1 (fr) * 2013-02-22 2014-08-28 Croda, Inc. Traitement de surfaces dures
WO2016155993A1 (fr) 2015-04-02 2016-10-06 Unilever Plc Composition
WO2017133879A1 (fr) 2016-02-04 2017-08-10 Unilever Plc Liquide détergent
WO2017211700A1 (fr) 2016-06-09 2017-12-14 Unilever Plc Produits de blanchisserie
WO2017211697A1 (fr) 2016-06-09 2017-12-14 Unilever Plc Produits de lessive
WO2018127390A1 (fr) 2017-01-06 2018-07-12 Unilever N.V. Composition d'élimination de taches
WO2018224379A1 (fr) 2017-06-09 2018-12-13 Unilever Plc Système de distribution de lessive liquide
WO2019038187A1 (fr) 2017-08-24 2019-02-28 Unilever Plc Perfectionnements se rapportant au nettoyage de tissus
WO2019038186A1 (fr) 2017-08-24 2019-02-28 Unilever Plc Perfectionnements se rapportant au nettoyage de tissus
WO2019063402A1 (fr) 2017-09-29 2019-04-04 Unilever Plc Produits de lessive
WO2019068473A1 (fr) 2017-10-05 2019-04-11 Unilever Plc Produits de lessive

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4001415A1 (de) * 1990-01-19 1991-07-25 Basf Ag Polyester, die nichtionische tenside einkondensiert enthalten, ihre herstellung und ihre verwendung in waschmitteln
DE19522431A1 (de) * 1994-08-11 1996-02-15 Huels Chemische Werke Ag Schmutzlösepolymere auf Basis von Oligoestern als Bestandteil von Formulierungen zur Ablösung von Öl- und Fettschmutz
EP0964015A1 (fr) * 1998-06-12 1999-12-15 Clariant GmbH Oligoester detachant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4001415A1 (de) * 1990-01-19 1991-07-25 Basf Ag Polyester, die nichtionische tenside einkondensiert enthalten, ihre herstellung und ihre verwendung in waschmitteln
DE19522431A1 (de) * 1994-08-11 1996-02-15 Huels Chemische Werke Ag Schmutzlösepolymere auf Basis von Oligoestern als Bestandteil von Formulierungen zur Ablösung von Öl- und Fettschmutz
EP0964015A1 (fr) * 1998-06-12 1999-12-15 Clariant GmbH Oligoester detachant

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011120799A1 (fr) 2010-04-01 2011-10-06 Unilever Plc Procédé de structuration de liquides détergents à l'aide d'huile de ricin hydrogénée
EP2495300A1 (fr) 2011-03-04 2012-09-05 Unilever Plc, A Company Registered In England And Wales under company no. 41424 of Unilever House Structuration de liquides détergents avec de l'huile de ricin hydrogénée
EP2476743A1 (fr) 2011-04-04 2012-07-18 Unilever Plc, A Company Registered In England And Wales under company no. 41424 of Unilever House Procédé de lavage du linge
WO2012136427A1 (fr) 2011-04-04 2012-10-11 Unilever Plc Procédé de lavage d'un tissu
WO2013139702A1 (fr) 2012-03-21 2013-09-26 Unilever Plc Particules de détergent à lessive
GB2525530B (en) * 2013-02-22 2018-11-14 Croda Inc Treatment of hard surfaces
WO2014130257A1 (fr) * 2013-02-22 2014-08-28 Croda, Inc. Traitement de surfaces dures
GB2525530A (en) * 2013-02-22 2015-10-28 Croda Inc Treatment of hard surfaces
CN105283533A (zh) * 2013-02-22 2016-01-27 禾大公司 硬表面的处理
WO2016155993A1 (fr) 2015-04-02 2016-10-06 Unilever Plc Composition
WO2017133879A1 (fr) 2016-02-04 2017-08-10 Unilever Plc Liquide détergent
WO2017211700A1 (fr) 2016-06-09 2017-12-14 Unilever Plc Produits de blanchisserie
WO2017211697A1 (fr) 2016-06-09 2017-12-14 Unilever Plc Produits de lessive
WO2018127390A1 (fr) 2017-01-06 2018-07-12 Unilever N.V. Composition d'élimination de taches
WO2018224379A1 (fr) 2017-06-09 2018-12-13 Unilever Plc Système de distribution de lessive liquide
WO2019038187A1 (fr) 2017-08-24 2019-02-28 Unilever Plc Perfectionnements se rapportant au nettoyage de tissus
WO2019038186A1 (fr) 2017-08-24 2019-02-28 Unilever Plc Perfectionnements se rapportant au nettoyage de tissus
WO2019063402A1 (fr) 2017-09-29 2019-04-04 Unilever Plc Produits de lessive
WO2019068473A1 (fr) 2017-10-05 2019-04-11 Unilever Plc Produits de lessive
DE212018000292U1 (de) 2017-10-05 2020-04-15 Unilever N.V. Waschmittelprodukte

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