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WO2025172319A1 - Améliorations apportées ou se rapportant à des composés organiques - Google Patents

Améliorations apportées ou se rapportant à des composés organiques

Info

Publication number
WO2025172319A1
WO2025172319A1 PCT/EP2025/053638 EP2025053638W WO2025172319A1 WO 2025172319 A1 WO2025172319 A1 WO 2025172319A1 EP 2025053638 W EP2025053638 W EP 2025053638W WO 2025172319 A1 WO2025172319 A1 WO 2025172319A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
aldehyde
dimethyl
malodour
alpha
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
Application number
PCT/EP2025/053638
Other languages
English (en)
Inventor
Elisabeth Rinaudo
Liliana DEUSAN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan SA
Original Assignee
Givaudan SA
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 Givaudan SA filed Critical Givaudan SA
Publication of WO2025172319A1 publication Critical patent/WO2025172319A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0068—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
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2079—Monocarboxylic acids-salts thereof
    • 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
    • C11D3/33—Amino carboxylic acids

Definitions

  • This disclosure is concerned with household cleaning compositions comprising a malodour- controlling component, as well as methods of deodorizing a site, or a location proximate to a site, treated with said compositions.
  • Household cleaning compositions are known in the art. They are useful to clean soils and residues, for example mineral and fatty soils or residues, from all manner of household surfaces including floors, bathroom and kitchen surfaces, as well as surfaces of household appliances, such as laundry washers or dryers, and automatic dish washing machines.
  • Household cleaning compositions can contain many functional ingredients known in the art. Many of these compositions contain ingredients known as "builders". Builders are used to prevent the build-up of sediments (such as lime scale) on surfaces as well as to enhance a composition's cleaning performance. Until relatively the builders of choice were based on phosphate chemistry. Phosphate builders possess the advantages of being inexpensive, being widely compatible with many other common components employed in household cleaning compositions, as well as being both cheap to source and widely available. In more recent times, however, their use has been legislated against in certain jurisdictions owing to perceived negative effects related to environmental pollution.
  • amino carboxylates are useful builders and can be used as a replacement for phosphates, and indeed, household cleaning compositions containing amino carboxylates are known in the art.
  • the malodour was found to be particularly noticeable when a cleaning compositions was removed from its packaging or when the compositions were used in cleaning operations carried out in enclosed spaces, such as household appliances, and more particularly automatic dishwasher machines. In such enclosed spaces an appreciable headspace concentration of the malodour can buildup to levels, which become noticeable to consumers in use.
  • the malodour was observed to be particularly noticeable when the door of a household appliance, such as a dishwasher machine, is opened at the end of a cleaning cycle.
  • the present invention is directed in a first aspect to a household cleaning composition
  • a household cleaning composition comprising one or more ingredients susceptible of causing the generation of an undesirable malodour, and a malodour-controlling component comprising zinc neodecanoate.
  • the present invention was based on the surprising discoveries that household cleaning compositions can contain ingredients that can be the source of undesirable malodours, which are particularly noticeable and particularly disturbing to consumers when the compositions are stored in enclosed spaces, such as packaging, or are used in cleaning operations carried out in enclosed spaces, such as dishwashing operations in automatic dishwashing machines, or indeed laundry operations carried out in washing machines.
  • Amino carboxylate builders such as MGDA, were discovered to be particularly susceptible of causing malodour.
  • MGDA MGDA
  • a clearly perceptible malodour was observed when opening and removing the dishwasher composition from packaging, and when a dish washer machine containing the composition was opened after a wash cycle.
  • the emanation of malodour at these moments in time corresponds with important touch-points for consumers, who according to consumer research are particularly sensitive to scent signals at precisely these time points.
  • the malodour controlling component of the household cleaning composition contains zinc neodecanoate.
  • Zinc neodecanoate is a zinc carboxylate, but unlike the water-soluble zinc carboxylates zinc acetate and zinc sulphate that have been employed in dish washing compositions, zinc neodecanoate is unusual in that it alone is capable of delivering malodour control.
  • the applicant believes that owing to zinc neodecanoate being a water-insoluble, viscous liquid, unlike the water-soluble carboxylates referred to above, in use it is able to form a film on surfaces that resists removal at least as long if not longer than the other water-soluble or water-dispersible components of the cleaning compositions according to the invention. As such, it is able to more effectively counteract any malodour generated.
  • the zinc neodecanoate may be used in admixture with a suitable diluent in which the zinc neodecanoate is soluble or miscible.
  • suitable diluents for this purpose should have a high clogP, for example a clogP of 1.5 or greater, and can include perfume ingredients, solvents used in perfumery, or mixtures thereof.
  • perfumery ingredients and solvents include those referred to in standard perfumery reference works of the perfume industry, for example in Arctander, Perfume and Flavour Chemicals (Aroma Chemicals), vol. I and II (1969), and any later volumes and editions of that work, which are hereby incorporated by reference.
  • particularly preferred solvents include isopropyl myristate or any other oily liquids that may be compatible with the household cleaning composition, such as silicones or the like.
  • the malodour-controlling component may further comprise one or more fragrance ingredients. Any fragrance ingredients may be employed in the malodour-controlling component, and including those ingredients described in the Arctander reference works referred to above.
  • fragrance ingredients employed can exert a malodour- counteracting effect.
  • perfumes include, but are not limited to aldehydes that are capable of exerting a malodour-reducing effect in either the liquid or gaseous phase by chemical reaction with malodorous ingredients.
  • aldehyde perfume ingredients include but are not limited to Adoxal (2,6,10-Trimethyl-9-undecenal), Bourgeonal (4-t- butylbenzenepropionaldehyde), Lilestralis 33 (2-methyl-4-t-butylphenyl)propanal), Cinnamic aldehyde, cinnamaldehyde (phenyl propenal, 3-phenyl-2-propenal), Citral, Geranial, Neral (dimethyloctadienal, 3,7-dimethyl-2,6-octadien-l-al), Cyclal C (2,4-dimethyl- 3-cyclohexen-l-carbaldehyde), Florhydral (3-(3-lsopropyl-phenyl)-butyraldehyde), Citronellal (3,7-dimethyl 6-octenal), Cymal, cyclamen aldehyde, Cyclosal, Lime aldehyde (Alp
  • Starches suitable for encapsulating fragrances are modified starches, which can be made from, raw starch, pre-gelatinized starch, modified starch derived from tubers, legumes, cereal and grains, for example corn starch, wheat starch, rice starch, waxy corn starch, oat starch, cassava starch, waxy barley, waxy rice starch, sweet rice starch, amioca, potato starch, tapioca starch and mixtures thereof.
  • Modified starches suitable for use as the encapsulating matrix include starches that are modified chemically, physically, e.g. through heat or pressure, or enzymatically. They include hydrolyzed starch, acid thinned starch, starch esters of long chain hydrocarbons, starch acetates, starch octenyl succinate, and mixtures thereof. Starch esters having a degree of substitution in the range of from about 0.01% to about 10.0% may be used to encapsulate the fragrance ingredients.
  • the hydrocarbon part of the modifying ester should be from a C5 to C16 carbon chain.
  • Suitable amino carboxylates for use in the household cleaning compositions according to the first aspect of the invention include but are not limited to ethylene diamine tetra acetates, diethylene triamine pentaacetates, diethylene triamine pentaacetate (DTPA), N- hydroxyethylethylenediamine triacetates, nitrilotriacetates, ethylenediamine tetrapropionates, triethylenetetraaminehexa-acetates, ethanol-diglycines, propylene diamine tetracetic acid (PDTA) and methyl glycine di-acetic acid (MGDA), both in their acid form, or in their alkali metal, ammonium, and substituted ammonium salt forms.
  • a particularly suitable amino carboxylate to be used herein is MGDA.
  • the amino carboxylate can be employed in amounts ranging from about 5 to about 95 wt % based on the total weight of the cleaning composition.
  • the household cleaning composition is a hard surface cleaning composition.
  • Hard-surface cleaning compositions are generally known in the art. They contain a number of conventional ingredients that can vary depending upon their particular format, and their intended purpose. Conventional ingredient include, but are not limited to acidic components useful for lime scale removal; alkaline components, useful to adjust the pH of the composition; surfactants; surface-modifying polymers; radical scavengers; solvents, and the like.
  • acidic components include but are not limited to formic acid, citric acid, acetic acid or oxalic acid.
  • the amounts of acidic components employed are from 0.1 to 5 wt % based on the total weight of the composition.
  • alkaline components include but are not limited to sodium hydroxide, potassium hydroxide, lithium hydroxide, the alkali metal oxides such, as sodium or potassium oxide, monoethanolamine, triethanolamine, ammonia, ammonium carbonate, choline base, and the like.
  • surfactants include but are not limited to anionic and non-ionic surfactants.
  • Anionic surfactants include but are not limited to alkyl sulphonates, alkyl aryl sulphonates, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts of soap, alkyl sulphates, alkyl aryl sulphates alkyl alkoxylated sulphates, C8-C24 olefinsulfonates, sulphonated polycarboxylic acids, alkyl ester sulphonates, acyl glycerol sulphonates, alkyl phosphates, isethionates, N-acyl taurates, alkyl succinamates, acyl sarcosinates, sulphates of alkyl polysaccharides, alkyl polyethoxy carboxylates, or mixtures thereof.
  • Non-ionic surfactants include but are not limited to alkoxylated alcohols, especially ethoxylated and/or propoxylated alcohols, the condensation products of ethylene oxide and/or propylene oxide with alcohols having a straight or branched alkyl chain, having from 6 to 22 carbon atoms, or mixtures thereof.
  • the amounts of surfactants employed are from 0.1 to 15 wt % based on the total weight of the cleaning composition.
  • surface-modifying polymers include but are not limited to vinylpyrrolidone homopolymers or copolymers, zwitterionic copolymers consisting of carboxylate and permanent cationic-moieties; zwitterionic polysulphobetaine copolymers; zwitterionic polybetaine copolymers; silicone glycol polymers, or mixtures thereof.
  • the amounts of surface-modifying polymers employed are from 0.01 to 5 wt% based on the total weight of the cleaning composition.
  • the amounts of radical scavengers employed are from 0.001 to 10.0 wt% based on the total weight of the cleaning composition.
  • solvents include but are not limited to all those known to those skilled in the art of hard-surfaces cleaner compositions.
  • Particular solvents include alkoxylated glycol ethers, such as n-Butoxy Propoxy Propanol (n-BPP)) or mixtures thereof.
  • the amounts of solvents employed are from 0.1 to 5 wt% based on the total weight of the cleaning composition.
  • Hard-surface cleaning compositions according to the invention may be presented in various formats, including powder, tablet or liquid formats.
  • the second aspect of the invention relates to a method of delivering a malodour reduction benefit to a site, or to a location proximate to a site, containing a source of malodour, said method comprising the step of applying to the site, a composition according to the first aspect of the invention.
  • amino carboxylates such as MGDA
  • MGDA amino carboxylates
  • the mechanism of pyrazine formation from compositions according to the invention is not known as it will depend upon the nature of the household cleaning composition and its constituent ingredients, as well as its conditions of use.
  • MGDA amino carboxylates and MGDA in particular, and without wishing to be bound by theory it is possible to form pyrazines by a sequence of cyclocondensation/reduction/decarboxylation or dealkylation of MGDA in the presence of reducing agents.
  • MGDA can also play the role of a catalytic agent in the presence of alphadiketones and diamines or alpha-amino ketones which condense to form pyrazines.
  • non-ionic surfactants or other ingredients derived from sugars, amino acids or their derivatives, (poly-)ethylene diamines or ethanol- or propanolamines can oxidize and lead to the formation of pyrazines.
  • the malodour comprises one or more of the pyrazine compounds 2,5-dimethyl pyrazine, 2-ethyl-6-methyl pyrazine, 2,3,5-trimethyl pyrazine and 2-ethyl-3,5-dimethyl pyrazine.
  • the use of zinc neodecanoate to reduce or eliminate a malodour caused by the emanation of a pyrazine compound, in particular when the source of that malodour is a household care product, more particularly a hard-surface cleaning composition, and more particularly still an automatic dishwashing composition, is not known in the art, and thus forms an additional aspect of the invention.
  • the invention also provides in yet another of its aspects a method of reducing or eliminating a malodour caused by the emanation of a pyrazine compound, the method comprising the step of applying to the source of the malodour zinc neodecanoate.
  • the source of the malodour can be a household cleaning composition as herein above described and so, accordingly, the invention provides in still another of its aspects a method of reducing or eliminating a malodour caused by the emanation of a pyrazine from a household cleaning composition, or from a site treated with said composition, the method comprising the step of incorporating a malodour-controlling component comprising zinc neodecanoate as herein above describe into said household cleaning composition.
  • the pyrazine is selected from the group consisting of 2,5-dimethyl pyrazine, 2-ethyl-6-methyl pyrazine, 2,3,5-trimethyl pyrazine and 2-ethyl-3,5-dimethyl pyrazine, or a mixture thereof.
  • the source of the malodour is an amino carboxylate, and more particularly MGDA.
  • the source of the malodour is a household cleaning composition, more particularly a hard-surface cleaning composition, and more particularly still an automatic dishwashing detergent composition, comprising at least one ingredient susceptible of generating a malodour, such as an amino carboxylate, and more particularly MGDA.
  • Zinc neodecanoate is a viscous ingredient and for a better handling, a solution at 81% in isopropyl myristate is employed in the following preparation.
  • a 100g sample of automatic dishwashing powder containing MGDA is poured into a glass container.
  • the solution of zinc neodecanoate in isopropyl myristate is added on top of the powder and the mixture stirred with a glass rod for at least 2 minutes.
  • the container is covered and the mix is left for overnight to macerate in the container. After 24h the powder is stirred again to produce a homogeneous, dry powder.
  • the amount of zinc neodecanoate solution added to the dishwashing powder can be varied to provide several test samples in order to study the effect of zinc neodecanoate concentration on the suppression of malodour.
  • the dishwashing powder base used in the present Example and described in the preparation of Example 1 contains MGDA.
  • the base has a strong malodour that can be described as earthy, roasted nuts, cocoa, coffee, caramel and baked potato-like.
  • MGDA-containing dishwashing powder samples were dosed with zinc neodecanoate, zinc ricinoleate and zinc acetate dehydrate in accordance with the method of Example 1.
  • a first sample contained 0.4 wt % zinc neodecanoate; a second sample contained 0.66 wt % zinc ricinoleate; and a third sample contained 0.22 wt % zinc acetate dehydrate. All three samples contained substantially the same amount of zinc ions.
  • each sample is placed in a Petri dish and each dish is placed inside a plastic bag in fluid communication with a Tenax tube.
  • a pump (low flow Gillian pump) draws the headspace constituents in the bag through the Tenax tube at a rate of 50 ml/min, whereupon the constituents are trapped on an absorbent material in the tube (2,6 diphenylene oxide sorbent material). Headspace sampling lasts 60 min with 60 min of saturation.
  • the Tenax tubes are afterwards desorbed in a TDS/GC/MS.
  • the GC analysis confirms that the peak areas of the identified pyrazines are not reduced in presence of zinc acetate nor with zinc ricinoleate whereas the areas of the peaks in the headspace decrease by half when zinc neodecanoate is used (Table 1).

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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)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne une composition de nettoyage domestique comprenant au moins un ingrédient susceptible de générer une mauvaise odeur, et un composant de lutte contre les mauvaises odeurs comprenant du néodécanoate de zinc, ainsi que des procédés de fourniture d'un bénéfice de réduction des mauvaises odeurs à un site d'une source de mauvaises odeurs ou à un espace à proximité de celui-ci.
PCT/EP2025/053638 2024-02-15 2025-02-12 Améliorations apportées ou se rapportant à des composés organiques Pending WO2025172319A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP24157829 2024-02-15
EP24157829.3 2024-02-15

Publications (1)

Publication Number Publication Date
WO2025172319A1 true WO2025172319A1 (fr) 2025-08-21

Family

ID=89977292

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2025/053638 Pending WO2025172319A1 (fr) 2024-02-15 2025-02-12 Améliorations apportées ou se rapportant à des composés organiques

Country Status (1)

Country Link
WO (1) WO2025172319A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018087147A1 (fr) 2016-11-10 2018-05-17 Givaudan Sa Agent désodorisant comprenant du néodécanoate de zinc
US20220387275A1 (en) * 2019-11-15 2022-12-08 Conopco, Inc., D/B/A Unilever Deodorant compositions
WO2023111164A9 (fr) * 2021-12-15 2023-07-20 Givaudan Sa Améliorations apportées à ou se rapportant à des composés organiques
WO2023237747A1 (fr) * 2022-06-10 2023-12-14 Unilever Ip Holdings B.V. Utilisations de compositions déodorantes pour réduire les mauvaises odeurs sur les vêtements

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018087147A1 (fr) 2016-11-10 2018-05-17 Givaudan Sa Agent désodorisant comprenant du néodécanoate de zinc
US20220387275A1 (en) * 2019-11-15 2022-12-08 Conopco, Inc., D/B/A Unilever Deodorant compositions
WO2023111164A9 (fr) * 2021-12-15 2023-07-20 Givaudan Sa Améliorations apportées à ou se rapportant à des composés organiques
WO2023237747A1 (fr) * 2022-06-10 2023-12-14 Unilever Ip Holdings B.V. Utilisations de compositions déodorantes pour réduire les mauvaises odeurs sur les vêtements

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