WO2001007095A1 - Compositions de traitement contre les mauvaises odeurs - Google Patents

Compositions de traitement contre les mauvaises odeurs Download PDF

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Publication number
WO2001007095A1
WO2001007095A1 PCT/EP2000/006550 EP0006550W WO0107095A1 WO 2001007095 A1 WO2001007095 A1 WO 2001007095A1 EP 0006550 W EP0006550 W EP 0006550W WO 0107095 A1 WO0107095 A1 WO 0107095A1
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WO
WIPO (PCT)
Prior art keywords
composition
perfume
aldehyde
compositions
compound
Prior art date
Application number
PCT/EP2000/006550
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English (en)
Inventor
Richard M. Boden
Alan John Fry
Barbara Ann Jones
Henricus Gerardus Maria Reijmer
William L. Schreiber
Adi Shefer
Stephen David Sims
Freddy Tabak
Original Assignee
Unilever Plc
Unilever Nv
Hindustan Lever Limited
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
Priority claimed from GBGB9917133.2A external-priority patent/GB9917133D0/en
Priority claimed from GBGB9917160.5A external-priority patent/GB9917160D0/en
Priority claimed from GBGB9922080.8A external-priority patent/GB9922080D0/en
Priority claimed from GB0000556A external-priority patent/GB2359750A/en
Application filed by Unilever Plc, Unilever Nv, Hindustan Lever Limited filed Critical Unilever Plc
Priority to AU61577/00A priority Critical patent/AU6157700A/en
Publication of WO2001007095A1 publication Critical patent/WO2001007095A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/04—Detergent materials or soaps characterised by their shape or physical properties combined with or containing other objects
    • C11D17/041—Compositions releasably affixed on a substrate or incorporated into a dispensing means
    • C11D17/046—Insoluble free body dispenser
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant 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
    • C11D3/2072—Aldehydes-ketones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/005—Compositions containing perfumes; Compositions containing deodorants
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/137—Acetals, e.g. formals, or ketals
    • 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
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/06—Processes in which the treating agent is dispersed in a gas, e.g. aerosols

Definitions

  • the present invention relates to liquid malodour treatment compositions comprising a deodorising perfume.
  • the invention also relates to a method of reducing or masking a malodour on a substrate by applying thereto a composition of the invention.
  • Household and personal items that are susceptible to taking up surrounding odours such as clothing and other fabric-containing articles, often come into contact with undesirable odours (e.g. tobacco, pet, body and cooking odours) . These odours are thus taken up by the item to create an undesirable odour on it .
  • undesirable odours e.g. tobacco, pet, body and cooking odours
  • perfumes to mask or cover malodours. These perfumes are formulated within a composition and are released therefrom to provide the perfuming effect. The perfumes may be controllably released e.g. to provide longer- lasting perfuming. Perfumes that are effective against malodours may be referred to as deodorising perfumes .
  • the perfume may be entrapped within a matrix to provide controlled perfume release properties .
  • WO 94/28107 discloses a perfume delivery system for covering the malodour of a composition, for example a granular detergent composition, and for providing a new aroma therefor.
  • the compositions comprise a solid, water- soluble porous carrier which comprises a natural or synthetic zeolite, a perfume releasably incorporated in the pores of the zeolite carrier, and, a matrix which comprises a water-soluble composition (in which the perfume is substantially insoluble) coated onto the perfumed zeolite.
  • compositions including colognes, aftershave lotions, after bath preparations and splash lotions which yield a continuously high fragrance intensity release .
  • the compositions can be adapted to qualitatively and quantitatively release differing aromas in a controlled manner.
  • the compositions are a mixture of a non- confined fragrance composition with one or more fragrance oils physically entrapped in one or more types of solid particles and a suspending agent e.g. hydroxypropyl cellulose.
  • malodour treatment perfumes include Neutriff and Galaxolide (both trademarks of International Flavours and Fragrances Inc.) .
  • Other materials which have been known to cover malodours include corn mint oil and citral .
  • acetals in perfumery are well known.
  • Japanese patent application number 110/29517 discloses that certain acetals produced by the reaction of an aldehyde or ketone with an alcohol (including a diol) in the presence of a given complex Nickel catalyst are suitable as synthetic starting materials for perfumes.
  • Korean patent application number 98/009214 Korean Ginseng and Tobacco Research Institute discloses pyruvaldehyde dimenthyl acetal and the preparation thereof.
  • EP 905 115 discloses a method for making an acetal compound comprising the step of adding a carbonyl compound (selected from an aldehyde, a ketone and mixtures thereof) , an alcohol and a dehydrating agent to an environment, and pressurising the mixture to cause the carbonyl compound and the alcohol to form the acetal .
  • a carbonyl compound selected from an aldehyde, a ketone and mixtures thereof
  • WO 97/34578 discloses a pro-fragrance compound selected from the group consisting of an acetal, a ketal, and mixtures thereof, wherein at least one of a parent aldehyde, ketone or alcohol of the pro-fragrance acetal or ketal is a fragrance compound having a Clog P of less than about 4.
  • WO 98/06803 discloses rinse added fabric softening compositions containing pro-fragrant acetals or ketals which hydrolyse upon exposure of surfaces rinsed in solution of said compositions to a reduction in pH. A fragrance which is characteristic of one or more of the hydrolysis products is thereby released.
  • liquid malodour treatment composition comprising;
  • aldehyde is: hexylcinnamic aldehyde; heliotropine; undecylenic aldehyde; dodecanal; compound (I) ; compound (II) , or compound (III) ; (I)
  • carbinol is: citronellol; nerol; geraniol; dihydromyrcenol; ⁇ -phenyl ethyl alcohol; tetrahydrolinalool; undecavertol; or compound (IV); (IV) CH 2 CH (CH 2 ), OH
  • ketone is: hedione; methyl ionone; or compound (V) ;
  • a cyclic triacetal or, a mixed cyclic triacetal of at least two aldehydes which are: heliotropine; undecylenic aldehyde; dodecanal; and/or compound (I), (II) or (III) as defined in (a) above.
  • solubilising aid (B) is present in the composition in an amount by weight sufficient to solubilise, disperse or emulsify the deodorising perfume (A) in the water.
  • the invention further provides a method of reducing or masking a malodour on a substrate, comprising the step of applying to the substrate a malodour-reducing amount of the above-defined composition.
  • Personal care deodorant, or anti-perspirant , malodour treatment compositions that are applied directly to the skin do not form part of the present invention.
  • the malodour treatment compositions of the invention comprise a deodorising perfume comprising at least one substance which is the reaction product of (i) an aldehyde with an alcohol, or (ii) a ketone with an alcohol or (iii) an aldehyde with the same or different aldehyde (s).
  • the perfume comprises:
  • a ketal or hemiketal produced by means of reacting a ketone with a carbinol, or a mixture of the ketal and hemiketal, or (c) a cyclic triacetal, or, a mixed cyclic triacetal of at least two aldehydes,
  • acetals, ketals, hemiacetals and hemiketals have the generic structures :
  • the terms Ki, K , K 3 , and K 4 are reaction rate constants and further wherein the terms Ri, i , R and R 2 define moieties resulting from the reactions of the following aldehydes and ketones with the following carbinols :
  • Aldehydes hexylcinnamic aldehyde, heliotropine, undecylenic aldehyde; dodecanal and aldehyde compounds (I) , (II) and (III) as defined herein.
  • Ketones hedione; methyl ionone and ketone compound (V) as defined herein.
  • Carbinols citronellol; nerol; geraniol; dihydromyrcenol; ⁇ - phenyl ethyl alcohol; tetrahydrolinalool; undecavertol and carbinol compound (IV) as defined herein.
  • the deodorising perfume comprises at least one substance which is an acetal or a hemiacetal as defined above, or mixtures thereof. Particularly preferred are the acetal and/or hemiacetal of hexylcinnamic aldehyde and dihydromyrcenol .
  • Compound (I) is available as LILIAL® from Givaudan Roure AG (Basel, Switzerland) .
  • Compounds (II) to (V) are commercially available from International Flavours and Fragrances Inc. as
  • cyclic triacetals produced by means of trimerization of a single aldehyde, or by reaction of different aldehydes with one another, may be used in the compositions of the invention.
  • Such cyclic triacetals have the structure:
  • R 7 , R 7 and R 7 are moieties created as a result of the reaction of the following aldehydes with one another or with themselves: heliotropine; undecylenic aldehyde, compound (I), and compound (III) .
  • hexylcinnamic aldehyde as used herein is meant the compound having the structure :
  • nerol as used herein is meant the compound having the structure:
  • acetals, hemiacetals, ketals, hemiacetals and triacetals decompose with time to form their constitute aldehydes, ketones, and alcohols, which are in and of themselves, taken alone, or in admixture, fragrance components or fragrance compositions.
  • the reactions to form the acetals, hemiacetals etc. may be shown as:
  • the concentration of the acetals, hemiacetals, ketals and hemiketals changes with time as they decompose on the substrate having the malodour to form their original aldehyde or ketone or the hemiacetals or hemiketals constituents which are also fragrance components or compositions.
  • the decomposition may occur by oxidation/reductive reactions when the products are placed in a basic, or even neutral, medium and exposed to air.
  • the reaction to form the acetals, ketals, and triacetals preferably takes place in the presence of an acid catalyst, especially citric acid.
  • the present invention concerns the use of specific ingredients for effecting controlled release of the perfume rather than the use of entrapped fragrances e.g. within a matrix, which has been used according to the prior art . It is thus preferred that the deodorising perfume is not present in the composition as an entrapped perfume .
  • the perfume may be present in the composition in an amount of 0.001 to 5% by weight, preferably 0.01 to 3% by weight, more preferably 0.01 to 2% by weight, most preferably 0.05 to 1% by weight, e.g. 0.1 to 0.75% by weight, based on the total weight of the composition.
  • compositions of the invention comprises a solubilising aid for the deodorising perfume .
  • solubilising aid is used herein for component (B) the term is to be construed as meaning that the solubilising aid either fully solubilises the perfume in the composition s aqueous phase, or, produces a dispersion or emulsion of the perfume therein.
  • solubilising aid is used herein, the term deodorising perfume solubiliser, dispersant or emulsifier could equally be used. The term is not intended to define only the full solubilisation of the perfume in the composition.
  • the solubilising aid is present in the composition in an amount by weight sufficient to solubilise, disperse or emulsify the perfume in the water which is present in the composition.
  • the solubilising aid comprises one or more surfactant (s) and/or one or more water-miscible solvent (s) .
  • the solubilising aid consists of one or more surfactants or a mixture of surfactant (s) and water-miscible solvent (s) .
  • the surfactant may be chosen from soap and non-soap anionic, cationic, nonionic, amphoteric and zwitterionic detergent-active compounds, and mixtures thereof.
  • suitable detergent-active compounds are available and are fully described in the literature, for example, in "Surface-Active Agents and Detergents", Volumes I and II, by Schwartz, Perry and Berch.
  • Suitable nonionic surfactants are also described in McCutcheon's "Detergents and Emulsifiers" North American Edition, 1994 Annual, incorporated herein by reference.
  • the surfactants are preferably water soluble, that is, they dissolve in water at 20 C at the concentration at which they are included in the compositions of the invention.
  • the preferred surfactants are anionic and/or nonionic surfactants .
  • nonionic surfactants are defined as substances with molecular structures consisting of a hydrophilic and hydrophobic part.
  • the hydrophobic part consists of a hydrocarbon and the hydrophilic part of polar groups.
  • Nonionic synthetic detergents may be broadly defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature.
  • the length of the hydrophilic or polyoxyalkylene radical which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
  • Suitable nonionic detergent surfactants are generally disclosed in U.S. Pat. No. 3,939,678, Laughlin et al . , issued Dec. 30, 1975, at column 13, line 14, through column 16, line 6, incorporated herein by reference.
  • Suitable nonionic surfactants include the primary and secondary alcohol alkoxylates, especially the Cs-C 2 aliphatic alcohols alkoxylated with an average of from 3 to 30 moles, especially 4 to 15 moles, of alkylene oxide per mole of alcohol, e.g. the C 9 -
  • Ci 8 primary and secondary aliphatic alcohols alkoxylated with an average of from 3 to 20, especially 4 to 15 moles of alkylene oxide per mole of alcohol.
  • the alcohols may be saturated or unsaturated, linear or branched.
  • Ethylene oxide is the preferred alkylene oxide.
  • Examples of such ethoxylated alcohols include the condensation product of C ⁇ -Ci 5 alcohol (predominantly) with about 9 moles of ethylene oxide per mole of alcohol ; and the condensation product of lauryl alcohol with about 20 moles of ethylene oxide.
  • nonionic surfactants of this type include NEODOL® 25-9 (the condensation product of C ⁇ 2 -Ci 5 alcohol with an average of 9 moles of ethylene oxide per mole of alcohol) , supplied by Shell Chemical Company, and GENAPOL® C200
  • PPG-1-PEG-9 lauryl glycol ether with an average of 9 moles of ethylene oxide per mole of alcohol (EUMULGIN® L, ex. Cognis Deutschland GmbH) .
  • nonionic surfactants are the polyethylene oxide condensates of oil and fats, e.g. lanolin, castor oil and hydrogenated castor oil . These compounds include ethoxylated hardened castor oils with greater than 60 wt% of the compound comprising the ethoxylate.
  • An example of a commercially available nonionic surfactant of this type is Cremophor C040, ex BASF (hardened castor oil with about 40 moles of ethylene oxide per mole of hardened castor oil) .
  • the polyethylene oxide condensates of alkyl phenols may also be used. These compounds include the condensation products of alkyl phenols having an alkyl group containing from about 6 to about 12 carbon atoms m either a straight chain or branched chain configuration with ethylene oxide, the ethylene oxide being present m an amount equal to from about 5 to about 25 moles of ethylene oxide per mole of alkyl phenol .
  • the condensation products of ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol may also be used. Also suitable are the condensation products of ethylene oxide with the products resulting from the reaction of propylene oxide and ethylenediamine, and ethoxylated fatty amides and ethoxylated fatty esters.
  • Preferred nonionic ethoxylated surfactants have an HLB of from about 7 to about 20, preferably from about 10 to about 15.
  • the nonionic ethoxylated surfactant solubilising aid preferably has 4-15 moles of ethylene oxide per molecule of alcohol.
  • Higher levels of ethoxylation e.g. 20 may suitably be used where a higher level of the given solubilising aid is used, and/or, where an additional solubilising aid is used.
  • nonionic surfactants examples include carbohydrate surfactants or other polyhydroxy surfactants e.g. alkyl polyglycosides as disclosed in EP 199 765 (Henkel) and EP 238
  • a polysaccharide e.g., a polyglycoside, hydrophilic group containing from about 1.3 to about 2.7 saccharide units are also useful.
  • Such polysaccharides are disclosed in U.S. Patent No. 4,565,647, Llenado, issued January 21, 1986.
  • Fatty acid amide surfactants having the formula:
  • R is an alkyl group containing from about 7 to about 21 (preferably from about 9 to about 17) carbon atoms and each R 1 is selected from the group consisting of hydrogen, Ci - C 4 hydroxyalkyl, and (C 2 H 4 ⁇ ) x H where x is from about 1 to about 3 may also be used.
  • Anionic surfactants that may be used include alkylbenzene sulphonate, particularly linear alkylbenzene sulphonate, and especially those having an alkyl chain length of Ce-Cis.
  • any conventional anionic surfactant may be used.
  • Examples include primary and secondary alkyl sulphates, particularly C 8 -C1 5 primary alkyl sulphates; alkyl ether sulphates and sulphonates; alkane sulphonates, olefin sulphonates; alkyl xylene sulphonates; dialkyl sulphosuccinates; alkyl acyl-N- (hydroxy) alkyl glucamine sulphates, alkyl ester sulphonates and fatty acid ester sulphonates .
  • Sodium, potassium and ammonium salts are generally preferred.
  • Soaps such as tallow, coconut, oleic and lauric fatty acid derived soaps and mixtures thereof are also suitable for use.
  • a mixture of anionic surfactant and nonionic surfactant may be used.
  • foaming products e.g. mousses
  • anionic surfactants either alone or in combination with nonionic surfactants.
  • Amphoteric and zwitterionic surfactants may also be used in the compositions of the invention.
  • Preferred types include amine oxides, betaines including sulphobetaines and tegobetaines, phosphine oxides and sulphoxides e.g. coco amido propyl betaine.
  • Amine oxides may also be used, for example, containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms e.g alkyl dimethyl amine oxide; water-soluble phosphine oxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the groups consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and a moiety selected from the groups consisting of alkyl and hydroxyalkyl moieties of from about 1 to about 3 carbon atoms.
  • the cationic surfactant may be a quaternary ammonium compound of formulae (A) below:
  • R and R are independently Ci-C ⁇ alkyl, alkenyl, substituted alkyl or alkenyl groups or hydroxyalkyl groups and
  • R and R are independently Cs-C 28 alkylalkenyl substituted alkyl
  • R and R 1 2 or alkenyl groups or hydroxalkyl groups.
  • R and R 1 2 or alkenyl groups or hydroxalkyl groups.
  • X is a compatible anion e.g. Cl , MeS0 4 , Br , I
  • Suitable, and more preferred, cationic surfactants are mono long chain alkyl cationic surfactants, preferably, quaternary ammonium salts of the general formula:
  • each R is a C1-C 4 alkyl or substituted (e.g. hydroxy)
  • the R group is C ⁇ o-C 22 hydrocarbon group, preferably C ⁇ 2 -C ⁇ s alkyl group or the corresponding ester linkage interrupted group with a short alkylene (C 1 -C 4 ) group between the ester linkage and the N, and having a similar hydrocarbon group, e.g., a fatty acid ester of choline, preferably C 12 -C 14 (coco) choline ester and/or C 16 -C1 8
  • ⁇ tallow choline ester and the counterion X is a compatible anion, e.g. halides such as chloride, methosulphate etc.
  • halides such as chloride, methosulphate etc.
  • An example is coconut alkyl (bishydroxyethyl) methyl ethoxylated methosulphate .
  • the surfactant may be present in an amount of from 0.01 to 15% by weight, based upon the total weight of the composition, preferably 0.05 to 10%, more preferably 0.1 to 5%, most preferably 0.15 to 3.5% by weight, for example 0.2 to 2%.
  • surfactant especially non-ionic surfactant, is used as the solubilising aid either alone or in conjunction with the water-miscible solvent solubilising aid below.
  • the solubilising agent preferably comprises a substantially water-miscible solvent .
  • substantially water-miscible solvent is meant that the solvent forms a single phase (homogenous) liquid when mixed with water at a 1:1 weight ratio at 20 C.
  • Mixtures of solvents may be used, as may, a mixture of a solvent with any of the above-identified surfactants.
  • the solvent is preferably a low molecular weight water-miscible solvent (preferably with a molecular weight of 200 or less) and preferably having a C ⁇ -C 6 alkyl chain.
  • the solvent may be an alcohol including monohydric alcohols and polyols (including diols) .
  • Suitable examples include ethanol (including refined de-natured ethanol; industrial methylated spirits) , isopropanol, n- propanol, and alkylene glycols including glycerol, dipropylene glycol, hexylene glycol, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, butyl digol, 2-methyl pentane 2,4-diol, and their derivatives and homologues .
  • the solvent when used, may be present in the same amounts by weight (based upon the total weight of the composition) as the surfactant solubilising aid defined above. Alternatively, the solvent may be present in an amount of up to 80% by weight, preferably 0.1 to 60%, more preferably 1 to 50%, most preferably 2 to 30%, e.g. 5 to 20% based on the total weight of the composition.
  • the weight ratio of total solubilising aid (B) to deodorising perfume (A) is usually 1:1 or greater, preferably 3:1 or greater. If the solubilising aid consists essentially of a surfactant the ratio is preferably in the range 30:1 to 3:1, more preferably 25:1 to 2:1, most preferably 10:1 to 3.5:1, e.g. 10:1 to 5:1. However if the solubilising aid consists essentially of a water-miscible solvent then the ratio is preferably in the range 5000:1 to 3:1, more preferably 500:1 to 40:1, most preferably 300:1 to 90:1, e.g. 250:1 to 150:1. However the exact ratios may depend to some extent on the nature of the solubilising aid. If a mixture of the surfactant and the ratio typically lies within that given for the solvent only systems .
  • compositions of the invention further comprise water.
  • the water is present in an amount of from 20% to 99.9% by weight, more preferably 30% to 99.8%, most preferably 40% to 99.5%, based on the total weight of the composition.
  • solubilising aid consists essentially of surfactants
  • water is preferably present in an amount of 80% by weight or more, more preferably 90% or more, e.g. 95% or more in the composition.
  • compositions are stable on storage at 0 C and 37 C for at least 24 hours, preferably at least 14 days.
  • stable is meant that do not become cloudy or separate into two or more phases visible to the naked eye.
  • the compositions exhibit this stability as is shown in the examples.
  • the perfume in the compositions does not gel or form a solid phase. If upon preparation of the compositions a cloudy, or two phase, product is formed the skilled person would know to increase the amount of solubility aid so that a clear, stable composition is formed.
  • these can be shaken and then used to treat malodours .
  • the composition can also contain one or more optional ingredients selected from: viscosity modifers, pH buffering agents, fluorescers, non-staining colorants or dyes or pigments, hydrotropes, anti-redeposition agents, enzymes, freeze-thaw stabilisers, optical brightening agents, opacifiers, anti- shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, drape imparting agents, antistatic agents, ironing aids, sequestrants, chlorine scavangers, dye fixing agents, anti- redeposition agents, sunscreens, insect repellents, anti-dye transfer agents, and stain repellent agents.
  • compositions of the invention include a film-forming polymer.
  • a film-forming polymer has been found to provide controlled release malodour treatment properties and/or controlled release perfume intensity properties for the compositions of the invention.
  • a polyvinyl acetate (PVA) especially, a partially hydrolysed PVA is a particularly preferred film-forming polymer.
  • a partially hydrolysed PVA exists as a mixture of PVA and PVOH with the proportions thereof being dependent upon the amount of hydrolysis.
  • the partially hydrolysed/substantially hydrolysed polyvinyl acetates preferably have a level of hydrolysis of between 70% and 99.9%, more preferably 73-99%, most preferably 75-98%, e.g. 80-98%. However, levels of hydrolysis down to 60% may be suitable in some cases .
  • the molecular weight of the partially hydrolysed/substantially hydrolysed polyvinyl acetate is preferably in the range 5,000 - 100,000, more preferably 10,000 - 80,000, most preferably 13,000
  • the film-forming polymer is preferably present in the compositions in an amount of 0.1 - 3% by weight based on the total weight of the composition, more preferably 0.15% - 2.5%, e.g. 0.2-2%.
  • the viscosity of the film-forming polymer at 20 C as a 4% solution is preferably in the range (in mPas measured by the Hoppler method), of 3-100, more preferably 5-70, most preferably 10-60.
  • a polymer group useful and particularly preferred is partially hydrolysed polyvinyl acetates, also termed polyvinyl alcohol , with polyvinyl acetate typically hydrolysed to an extent of from about 73% up to about 99%.
  • Such material is prepared by means of any of Examples I-XIV of U.S. Letters Patent No. 5,051,222 issued on September 24, 1999, the specification for which is incorporated by reference herein.
  • the partially hydrolysed polyvinyl acetate may be further hydrolysed to form polyvinyl alcohol with very few acetyl groups present (thereby forming, for example, 99% hydrolysed polyvinyl acetate) .
  • Preferred commercially available (hydrolysed) polyvinyl acetates include, the PVA polymers available under the following trade names (which are all believed to be trademarks) .
  • MOWIOLS ® (ex. Hoechst A.G., Germany); ARVOL 205 ® and VINEXS ® (both ex. Air products and Chemicals, USA) ;
  • GOHSEFIMERS ® (ex. Nippon Gohsei KK, Japan) ; ELVANOLS ® (ex. Du Pont Company, US) ; ALCOTEXS ® (ex. Harlow Chemical Company, UK) ; GOHSENOLS ® (ex.
  • compositions of our invention provides the additional advantage of an enhanced sensory impression of the perfume because of the increased duration of its release from the treated surface. It is also believed that an enhanced sensory impression of malodour treatment and/or freshness is obtained because of the increased duration of the perfume ingredients that make up the top notes of the perfume. Furthermore, it is also believed that triggered release of the fragrance from the treated surface can be possible upon the addition of moisture.
  • compositions of the invention comprise a film-forming polymer
  • compositions are beneficially made by adding a perfume/solubilising aid (e.g. nonionic surfactant) mixture to a mixture of the film-forming polymer in water.
  • a perfume/solubilising aid e.g. nonionic surfactant
  • a particularly preferred optional ingredient is a preservative.
  • Suitable preservatives include antimicrobial preservatives e.g. biocidal compounds, (substances that kill microorganisms) , and biostatic compounds (substances that inhibit and/or regulate the growth of microorganisms) .
  • the preservative may be any water-soluble organic or inorganic preservative which will not cause damage to fabric appearance, e.g. discolouration, colouration or bleaching.
  • Preferred water soluble preservatives include organic sulphur compounds, halogenated compounds, cyclic organic nitrogen compounds, low molecular weight aldehydes, quaternary compounds, dehydroacetic acid, phenyl and phenoxy compounds, and mixtures thereof.
  • Non-limiting examples of the preferred water soluble preservatives include 1, 2-benzisothiazolin-3-one, a broad spectrum preservative (PROXEL®, ex-Zeneca or Nipacide ® , ex. Nipa) ; a mixture of about 77% 5-chloro-2-methyl-4-isothiazolin- 3-one and about 23% 2-methyl-4-isothiazolin-3-one, (KATHON® CG, ex-Rohm and Haas Co); 2-bromo-2-nitropropane-l, 3-diol, (BRONOPOL®, ex-Inolex) ; a 95:5 mixture of 1,3- bis (hydroxymethyl) -5, 5-dimethy-2, 4-imidazolidinedione and 3- butyl-2-iodopropynyl carbamate (GLYDANT PLUS®, ex-Lonza) . It is especially preferred that the preservative used does not produce a darkening of the colour of the composition
  • a broad spectrum preservative e.g. one that is effective on both bacteria (gram positive and gram negative) and fungi.
  • a limited spectrum preservative i.e. one that is only effective on a single group of microorganisms e.g. fungi, can be used in combination with a broad spectrum preservative or another limited spectrum preservative with complementary and/or supplementary activity. Mixtures of any types of preservatives can also be used.
  • the preservative is included at an amount sufficient to prevent spoilage, or, prevent growth of microorganisms in the composition.
  • Preferred active levels of preservative are from about 0.0001% to about 0.75% by weight, more preferably from about 0.0002% to about 0.6%, most preferably from about 0.0003 to about 0.5%, by weight of the composition.
  • Another optional ingredient is an antifoam to reduce foam levels during manufacture and handling and/or use.
  • Inclusion levels are typically from about 0.0001% to about 0.5%, e.g. from about 0.001% to about 0.2% by weight of the composition.
  • the malodour treatment compositions of the invention are preferably substantially free of zeolite.
  • substantially free is meant that the composition comprises less than 0.5%, e.g. less than 0.1% of zeolite.
  • compositions are also preferably substantially free (as defined above) of fabric softening compounds conventionally used in fabric softening/rinse compositions.
  • the compositions may however contain the cationic surfactants defined above as solubilising agents. If the cationic surfactants defined as solubilising agents are present, it is preferred that they are present in amounts of 2% or less by weight, preferably 1% or less.
  • compositions are preferably free of dyes or colourants that undesirably discolour or stain the substrate to be which the composition is applied.
  • compositions comprise less than a total of 2% by weight of free acids (e.g. Boric acid) and free alkalis (e.g. sodium hydroxide) .
  • free acids e.g. Boric acid
  • free alkalis e.g. sodium hydroxide
  • compositions of the invention are in a liquid form, preferably in a form suitable for spraying onto the substrate to be treated.
  • the substrate is not living human or animal skin, fur, hair etc. It is also possible to formulate the compositions as foams or mousses, although a liquid-spray form is preferred.
  • compositions are preferably used on a substrate (e.g. fabrics etc.) that is not being concurrently subjected to a laundering operation such as washing or rinsing.
  • a substrate e.g. fabrics etc.
  • the substrate may be wetted slightly before the composition of the invention is applied.
  • compositions of the invention may be made by any suitable method.
  • the solubilising aid and perfume may be pre-mixed and then added to the water.
  • the optional ingredients may be added at any suitable time in the process.
  • the present invention also relates to a method of reducing or masking a malodour on a substrate.
  • the compositions of the invention are applied to the substrate in an amount sufficient to give a malodour reducing or masking effect .
  • compositions may be applied to the chosen substrate by any suitable method, e.g. by spraying directly onto the substrate, by applying a foam or mousse by dabbing/padding etc onto the substrate. Spraying onto the substrate is the preferred method.
  • the substrate may be any substrate as above which has a malodour which it is desired to remove.
  • Preferred substrates are fabric- containing substrates or items . Examples of such substrates include clothing items, upholstered items and soft furnishings (e.g. curtains), tableware, animal bedding and soft toys. Clothing includes shoes, coats, jackets etc.
  • the compositions of the invention are not intended to be applied directly to the human body or to an animal body.
  • the types of malodours that may be treated with the compositions of the invention include any undesirable odour e.g. tobacco odours, smoke, cooking odours, animal originating odours, body odours and musty smells.
  • the compositions of the invention may be packaged in any suitable dispenser, e.g. a pump or spray dispenser. Especially preferred are hand-operated spray units which can be used to spray the composition directly on to the substrate.
  • each mixture is stirred for a period of 72 hours .
  • each mixture is sprayed onto cloth odorised with stale tobacco aroma .
  • composition (ii) had the stale tobacco aroma completely removed and/or covered and the cloth had a pleasant, floral aroma.
  • Formulation A and formulation B were then stirred for a period of 72 hours. At the end of the 72 hours, each of formulations A and B were placed into 100ml pump dispensers.
  • the tea towels sprayed with formulation A had an aroma intensity scaled at 10 on a scale of 1-10 as assessed by a 30-member panel .
  • the tea towels sprayed with formulation B had a value of 5 for intensity as assessed by the 30-member panel.
  • the tea towels sprayed with formulation A had a pleasant aroma which lasted for a period of 144 hours at the same level as assessed by the 30-member panel.
  • the tea towels sprayed with formulation B, after 144 hours had an aroma scaled at 1 by the 30-member panel.
  • the acetal-containing formulation A is far superior for both substantivity and strength to the non-reacted component in formulation B.
  • Example 3 solvent and surfactant containing examples
  • compositions containing partially hydrolysed PVA were prepared by pre-mixing the perfume and Eumulgin L and then adding the preservative and water.
  • Example 4A is a comparative composition (which is still according to the invention) but which does not contain PVA. All percentages are by weight .
  • compositions were sprayed onto cotton fabric pieces (30cm x 20cm) at a dosage of between 0.9-1.0 gram per square.
  • the fragrance intensity was measured by assessors who smelt the treated cotton pieces after 5 and 7 days.
  • Each assessor smelt the treated cotton pieces and made a comparison of example 4A with 4.1, and separately, 4A with 4.2. After 5 and 7 days the fabrics were sprayed with water at a dosage of between 0.9-1.0 grams on each piece to determine if there was any change in fragrance intensity.
  • composition (5.1) comprising 0.20%wt of a perfume mixture comprising perfume of Example l.ii, water, preservative and a nonionic surfactant was prepared.
  • composition (5.2) comprising 0.20wt% of the same perfume but where the pre-reaction of the aldehyde/ketone with the Carbinol had not occurred was also prepared.
  • the two samples were placed into separate 100ml dispensers and lOg of one of the samples was sprayed evenly onto a cotton tea- towel which had previously been washed in an unfragranced detergent powder.
  • the other sample was similarly sprayed onto such a tea-towel.
  • the sprayed tea-towels were left for 72 hours in identical storage conditions and then assessed for perfume intensity by 10 panellists who assessed which was the most intensely perfumed tea towel .
  • the table below shows the % of panellists assessing each tea towel as the most intensely perfumed.
  • compositions in the table below having a single surfactant as the solubilising aid (B) , were prepared by mixing the perfume with the surfactant, followed by addition of the preservative and then the demineralised water. The compositions were then stored at 0 C and 37 C for two weeks to assess the physical stability of the products. All % are in % by weight based on the total amount of the composition.
  • the perfume used comprised the perfume mixture of Example l.ii above.
  • EMPIGEN® EMPIGEN® OC/E, Alkyl dimethylamine oxide (ex Albright
  • EMAL® EMAL® 270D/EG, Sodium Alkyl Ether Sulphate 2 EO (ex
  • REWOQUAT® REWOQUAT® CPEM, Coconut alkyl (bis hydroxyethyl) methyl ethoxylated methosulphate (ex Goldsmith) .
  • Examples 6.1 to 6.9 were physically stable at the end of the two week storage tests.
  • Examples 6.10 to 6.14 became cloudy and showed physical separation within a day of preparation, or did not produce a homogenous composition initially. However, after shaking, the compositions could still be used to provide the desired treatment of malodours .
  • compositions in the table below, having a mixture of surfactants as the solubilising aid (B) were prepared following the method of example 6 but using said mixture.
  • the storage of the compositions, the percentages and the perfume used are all as for Example 6.
  • Examples 7.1 to 7.3 were physically stable at the end of the two week storage tests.
  • Examples 7.4 and 7.5 became cloudy and showed physical separation within a day of preparation, or did not produce a homogenous composition initially. However, after shaking, the compositions could still be used to provide the desired treatment of malodours.
  • compositions in the table below having a mixture of surfactant and a water miscible solvent as the solubilising aid (B) , were prepared following the method of example 6 but with the solvent and surfactant added before the perfume was added.
  • the storage of the compositions, the percentages and the perfume used are all as for Example 6.
  • Examples 8.1 and 8.2 were physically stable at the end of the two week storage tests.
  • Examples 8.3 and 8.4 became cloudy and showed physical separation within a day of preparation, or did not produce a homogenous composition initially. However, after shaking, the compositions could still be used to provide the desired treatment of malodours,
  • compositions in the table below, having a water miscible solvent as the solubilising aid (B) were prepared following the method of example 6 but with the solvent used instead of the surfactant.
  • the storage of the compositions, the percentages and the perfume used are all as for Example 6.
  • Examples 9.1 to 9.4 were physically stable at the end of the two week storage tests.
  • Examples 9.5 to 9.8 became cloudy and showed physical separation within a day of preparation, or did not produce a homogenous composition initially. However, after shaking, the compositions could still be used to provide the desired treatment of malodours.

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

Abstract

La présente invention concerne des compositions de traitement contre les odeurs désagréables qui contiennent un parfum désodorisant, un adjuvant de solubilisation associé et de l'eau. Ces compositions sont utilisées pour traiter les odeurs indésirables sur un article sans qu'il soit nécessaire de le laver. Le parfum comprend: (a) un acétal ou un hémi-acétal produit par la réaction d'un aldéhyde avec un carbinol, ou (b) un cétal ou un hémi-cétal produit par la réaction d'une cétone avec un carbinol, ou (c) un triacétal cyclique d'un aldéhyde. L'aldéhyde peut être l'aldéhyde hexylcinnamique; l'héliotropine; l'aldéhyde undécylénique; le dodécanal ou un composé de formule (I) (II) ou (III). La cétone est l'hédione; l'ionone méthyle ou un composé tel que (V). Le carbinol est le citronellol; le nérol; le géraniol; le dihydromyrcénol; l'alcool β-phényle éthyle; le tétrahydrolinalool; l'undécavertol ou (IV). Il est véritablement préférable que les compositions contiennent un polymère filmogène, par exemple de l'acétate de polyvinyle et/ou au moins de l'acétate de polyvinyle partiellement hydrolysé. On décrit un procédé qui permet de traiter des articles dégageant une odeur désagréable au moyen de l'application de ces mêmes compositions.
PCT/EP2000/006550 1999-07-21 2000-07-11 Compositions de traitement contre les mauvaises odeurs WO2001007095A1 (fr)

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AU61577/00A AU6157700A (en) 1999-07-21 2000-07-11 Malodour treatment compositions

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
GB9917133.2 1999-07-21
GBGB9917133.2A GB9917133D0 (en) 1999-07-21 1999-07-21 Malodour treatment compositions
GB9917160.5 1999-07-22
GBGB9917160.5A GB9917160D0 (en) 1999-07-22 1999-07-22 Maldour treatment compositions
GBGB9922080.8A GB9922080D0 (en) 1999-09-17 1999-09-17 Malodour treatment compositions
GB9922080.8 1999-09-17
GB0000556A GB2359750A (en) 2000-01-11 2000-01-11 Malodour treatment composition comprising (hemi)acetal, (hemi)ketal or (mixed) cyclic triacetal obtained by reacting certain aldehydes/ketones with carbinols
GB0000556.1 2000-01-11

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WO2010020954A1 (fr) * 2008-08-22 2010-02-25 Firmenich Sa Mélanges dynamiques équilibrés contenant des hémiacétals stabilisés pour la libération contrôlée d'alcools actifs
EP2248881A1 (fr) 2002-05-23 2010-11-10 The Procter and Gamble Company Méthodes et articles pour reduire les particules aériennes
WO2018024511A1 (fr) 2016-08-05 2018-02-08 Unilever Plc Améliorations apportées et se rapportant au rafraîchissement de vêtements
WO2018094314A1 (fr) 2016-11-21 2018-05-24 Bell Flavors & Fragrances, Inc. Composition de neutralisation des mauvaises odeurs et méthodes
WO2019063402A1 (fr) 2017-09-29 2019-04-04 Unilever Plc Produits de lessive
WO2019068472A1 (fr) 2017-10-05 2019-04-11 Unilever Plc Procédés et dispositifs pour la lessive individualisée
WO2019072647A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Composition de pulvérisation aqueuse
WO2019073089A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Améliorations apportées et relatives au ravivage de vêtements
WO2019072643A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Composition aqueuse de pulvérisation
WO2019072648A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Compositions à vaporiser sur tissus
WO2019072644A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Composition aqueuse de pulvérisation
WO2019072645A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Composition aqueuse en aérosol
WO2021018805A1 (fr) 2019-07-30 2021-02-04 Unilever Global Ip Limited Compositions de pulvérisation pour tissu
WO2021110345A1 (fr) 2019-12-02 2021-06-10 Unilever Ip Holdings B.V. Sprays pour tissu
WO2021110346A1 (fr) 2019-12-02 2021-06-10 Unilever Ip Holdings B.V. Vaporisateurs de tissu
EP2539505B2 (fr) † 2010-02-23 2021-09-01 Ahlstrom-Munksjö Oyj Support a base de fibres cellulosiques contenant une couche de pva modifie, ainsi que son procede d'elaboration et son utilisation.
US11131055B2 (en) 2018-02-26 2021-09-28 Conopco, Inc. Methods and system for monitoring and replenishing one or more laundry components
WO2022043454A1 (fr) 2020-08-27 2022-03-03 Unilever Ip Holdings B.V. Conditionneur de tissu pour vêtement de sport
WO2022053251A1 (fr) 2020-09-09 2022-03-17 Unilever Ip Holdings B.V. Composition en aérosol pour linge
WO2022152476A1 (fr) 2021-01-13 2022-07-21 Unilever Ip Holdings B.V. Composition de lessive à pulvériser
WO2022219111A1 (fr) 2021-04-15 2022-10-20 Unilever Ip Holdings B.V. Composition à pulvériser pour tissu
US11910982B2 (en) 2019-11-01 2024-02-27 Conopco Inc. Recyclable auto-dosing container

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US6956013B2 (en) 2001-04-10 2005-10-18 The Procter & Gamble Company Photo-activated pro-fragrances

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Publication number Priority date Publication date Assignee Title
EP2248881A1 (fr) 2002-05-23 2010-11-10 The Procter and Gamble Company Méthodes et articles pour reduire les particules aériennes
WO2010020954A1 (fr) * 2008-08-22 2010-02-25 Firmenich Sa Mélanges dynamiques équilibrés contenant des hémiacétals stabilisés pour la libération contrôlée d'alcools actifs
CN102089037A (zh) * 2008-08-22 2011-06-08 弗门尼舍有限公司 用于活性醇受控释放的含稳定化的半缩醛的平衡动态混合物
EP2539505B2 (fr) † 2010-02-23 2021-09-01 Ahlstrom-Munksjö Oyj Support a base de fibres cellulosiques contenant une couche de pva modifie, ainsi que son procede d'elaboration et son utilisation.
WO2018024511A1 (fr) 2016-08-05 2018-02-08 Unilever Plc Améliorations apportées et se rapportant au rafraîchissement de vêtements
WO2018094314A1 (fr) 2016-11-21 2018-05-24 Bell Flavors & Fragrances, Inc. Composition de neutralisation des mauvaises odeurs et méthodes
WO2019063402A1 (fr) 2017-09-29 2019-04-04 Unilever Plc Produits de lessive
WO2019068472A1 (fr) 2017-10-05 2019-04-11 Unilever Plc Procédés et dispositifs pour la lessive individualisée
US11807974B2 (en) 2017-10-05 2023-11-07 Conopco, Inc. Methods and devices for individualized laundry
DE112018004426T5 (de) 2017-10-05 2020-05-20 Unilever N.V. Verfahren und Vorrichtungen für individualisierte Wäsche
WO2019073090A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Améliorations apportées et relatives au ravivage de vêtements
WO2019073089A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Améliorations apportées et relatives au ravivage de vêtements
WO2019072648A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Compositions à vaporiser sur tissus
WO2019072646A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Améliorations apportées et se rapportant au rafraîchissement de vêtements
WO2019072645A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Composition aqueuse en aérosol
WO2019072643A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Composition aqueuse de pulvérisation
WO2019072647A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Composition de pulvérisation aqueuse
WO2019072644A1 (fr) 2017-10-13 2019-04-18 Unilever Plc Composition aqueuse de pulvérisation
US11131055B2 (en) 2018-02-26 2021-09-28 Conopco, Inc. Methods and system for monitoring and replenishing one or more laundry components
WO2021018805A1 (fr) 2019-07-30 2021-02-04 Unilever Global Ip Limited Compositions de pulvérisation pour tissu
US11910982B2 (en) 2019-11-01 2024-02-27 Conopco Inc. Recyclable auto-dosing container
WO2021110346A1 (fr) 2019-12-02 2021-06-10 Unilever Ip Holdings B.V. Vaporisateurs de tissu
WO2021110345A1 (fr) 2019-12-02 2021-06-10 Unilever Ip Holdings B.V. Sprays pour tissu
WO2022043454A1 (fr) 2020-08-27 2022-03-03 Unilever Ip Holdings B.V. Conditionneur de tissu pour vêtement de sport
WO2022053251A1 (fr) 2020-09-09 2022-03-17 Unilever Ip Holdings B.V. Composition en aérosol pour linge
WO2022152476A1 (fr) 2021-01-13 2022-07-21 Unilever Ip Holdings B.V. Composition de lessive à pulvériser
WO2022219111A1 (fr) 2021-04-15 2022-10-20 Unilever Ip Holdings B.V. Composition à pulvériser pour tissu

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