WO2022023547A1 - Eutectiques profonds hydrophobes non ioniques en tant qu'agent désodorisant - Google Patents

Eutectiques profonds hydrophobes non ioniques en tant qu'agent désodorisant Download PDF

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WO2022023547A1
WO2022023547A1 PCT/EP2021/071440 EP2021071440W WO2022023547A1 WO 2022023547 A1 WO2022023547 A1 WO 2022023547A1 EP 2021071440 W EP2021071440 W EP 2021071440W WO 2022023547 A1 WO2022023547 A1 WO 2022023547A1
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acid
noni
alkyl
alkenyl
hba
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PCT/EP2021/071440
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English (en)
Inventor
Xavier Fernandez
Nicolas PAPAICONOMOU
Camille SCOTTO
Alix BERGER
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Centre National De La Recherche Scientifique
Université Cote D'azur
Universite Savoie Mont Blanc
Universite Grenoble Alpes
Grenoble Inp
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Publication of WO2022023547A1 publication Critical patent/WO2022023547A1/fr

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • A61L2209/00—Aspects relating to disinfection, sterilisation or deodorisation of air
    • A61L2209/10—Apparatus features
    • A61L2209/13—Dispensing or storing means for active compounds
    • A61L2209/133—Replaceable cartridges, refills
    • 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
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/02—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air by heating or combustion
    • A61L9/03—Apparatus therefor
    • 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
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
    • A61L9/12—Apparatus, e.g. holders, therefor
    • A61L9/127—Apparatus, e.g. holders, therefor comprising a wick
    • 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
    • A61L9/14—Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes

Definitions

  • the present invention relates to a process for deodorizing air by spraying a eutectic composition comprising a non-ionic hydrogen bond acceptor and a non-ionic hydrogen bond donor, within said air. It also relates to a deodorizing product comprising such eutectic composition.
  • TECHNICAL BACKGROUND Unpleasant odors originating from industries, cities or homes are a true problem in our society. Such odors are perceived as an aggression by the population, and they have become, like noise, one of the most frequent causes of complaints.
  • Odor masking by means of a spray comprising synthetic or natural chemicals, such as aldehydes or esters, is advantageously cheap and convenient. However, such strategy usually only hides the odor without eliminating the latter. Eliminating the malodorous volatile molecules can be achieved by using specific chemicals which are able to interact therewith.
  • silica particles are used in many commercial sprays and have an ability to attract the volatile molecules on their surface.
  • Zinc ricinolate is also able to create strong interactions with carboxyl-based, sulfur-based, or nitro-based volatile molecules.
  • Deep eutectic solvents are a new class of green solvents which combine a hydrogen bond acceptor (HBA) and a hydrogen bond donor (HBD), and have a very low melting point compared with HBA and HBD taken individually.
  • HBA hydrogen bond acceptor
  • HBD hydrogen bond donor
  • WO 2018/091379 describes a process for purifying a gaseous effluent containing volatile organic compounds (VOC), using a deep eutectic solvent comprising an ammonium or phosphonium halide as a HBA, and a HBD which is able to form a complex with the halide anion of the HBA.
  • VOC volatile organic compounds
  • these ionic DES’s allow to obtain high purification yields for a poor diversity of volatile compounds, and may have a relatively high viscosity (several hundreds of mPa.s at room temperature) which can limit the applications, in particular their use in sprays.
  • NonI-HBD specific non-ionic hydrogen bond acceptors
  • NonI- HBA specific non-ionic hydrogen bond donors
  • High performances have been demonstrated for a wide diversity of malodors, including hydrocarbons, carboxylic acids, thiols, disulfides, sulphur, esters, alcohols, isocyanates, ketones, or even heterocycles.
  • the hydrophobic DES used in the present invention have a viscosity lower than 100 mPa.s or even, lower than 20 mPa.s at 25°C (or at 20 °C), which makes them well-suited for applications in sprays.
  • DES’s used in the present invention can be produced by combining cheap and bio-sourced NonI-HBD’s and NonI-HBA’s, and thus appear as a cost-efficient and eco-friendly alternative deodorizing agent.
  • the present invention relates to a process for deodorizing air comprising at least one malodor, said process comprising: (a) contacting a eutectic composition with said air, said eutectic composition comprising a non- ionic hydrogen bond acceptor (NonI-HBA) and a non-ionic hydrogen bond donor (NonI-HBD), wherein: said NonI-HBA is selected from the group consisting of a monoterpenoid, a phenyl propanoid, POR3 with each R being independently a C 1 -C 16 hydrocarbon group, 1-naphthol, phenethyl alcohol, C 1 -C 12 alkyl anthranilate, C 2 -C 12 alkenyl anthranilate, maltol and lidocaine, and said NonI-HBD is selected from the group consisting of C 6 -C 22 phenols, C 3 -C 22 carboxylic acids, monoterpenoids and phenylpropanoids;
  • FIGURES Figure 1 is a schematic HS-SPME experiment in vial (left) performed on a mixture of malodors, with their corresponding signals after GC detection (right).
  • Figure 2 is a schematic view of the device used to perform an HS-SPME experiment in a chamber on a mixture of malodors, followed by the introduction of a eutectic composition of this invention into the chamber.
  • Figure 3 is a chromatogram showing the signals of the malodors introduced into the chamber illustrated on Figure 2.
  • C 1 -C 3 C 1 -C 6 or C 2 -C 6 can also be used with lower numbers of carbon atoms such as C 1 -C 2 , C 1 -C 5 , or C 2 -C 5 . If, for example, the term C 1 -C 3 is used, it means that the corresponding hydrocarbon chain may comprise from 1 to 3 carbon atoms, especially 1, 2 or 3 carbon atoms.
  • C 1 -C 6 it means that the corresponding hydrocarbon chain may comprise from 1 to 6 carbon atoms, especially 1, 2, 3, 4, 5 or 6 carbon atoms. If, for example, the term C 2 -C 6 is used, it means that the corresponding hydrocarbon chain may comprise from 2 to 6 carbon atoms, especially 2, 3, 4, 5 or 6 carbon atoms.
  • C 1 -C 16 hydrocarbon group refers to an acyclic or cyclic, saturated or unsaturated, aliphatic or aromatic hydrocarbon group having 1 to 16 carbon atoms.
  • C 1 -C 16 hydrocarbon group examples include, but are not limited to, C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 3 -C 16 cycloalkyl, and aryl.
  • alkyl refers to a saturated, linear or branched aliphatic group.
  • C 1 -C 16 alkyl examples are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, or hexadecyl.
  • alkenyl refers to an unsaturated, linear or branched aliphatic group comprising at least one carbon-carbon double bound.
  • C 2 -C 16 alkenyl examples include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, prenyl, hexenyl, decenyl, dodecenyl, tetradecenyl, or hexadecenyl.
  • cycloalkyl corresponds to a saturated or unsaturated mono-, bi- or tri-cyclic alkyl group having between 3 and 16 atoms of carbons (also named (C 3 -C 16 )cycloalkyl). It also includes fused, bridged, or spiro-connected cycloalkyl groups.
  • cycloalkyl includes for instance cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • cycloalkyl may also refer to a 5-10 membered bridged carbocyclyl such as bicyclo[2,2,1]heptanyl, bicyclo[2,2,2]octanyl, or adamantyl.
  • the “cycloalkyl” is a cyclopentyl or a cyclohexyl.
  • aryl corresponds to a mono- or bi-cyclic aromatic hydrocarbons having from 6 to 14 carbon atoms (also named (C 6 -C 1 4)aryl).
  • aryl includes phenyl, or naphthyl.
  • the aryl is a phenyl.
  • a eutectic composition used in the present invention comprises a non-ionic hydrogen bond acceptor (NonI-HBA) and a non-ionic hydrogen bond donor (NonI-HBD), wherein: said NonI-HBA is selected from the group consisting of a monoterpenoid, a phenyl propanoid, POR 3 with each R being independently a C 1 -C 16 hydrocarbon group, 1-naphthol, phenethyl alcohol, C 1 -C 1 2 alkyl anthranilate, C 2 -C 1 2 alkenyl anthranilate, maltol and lidocaine, and said NonI-HBD is selected from the group consisting of C 6 -C 2 2 phenols; C 3 -C 2 2 carboxylic acids, monoterpenoids and phenylpropanoids.
  • the term “eutectic composition” refers to a composition comprising a non-ionic hydrogen bond acceptor (NonI-HBA) and a non-ionic hydrogen bond donor (NonI-HBD), wherein the melting point of the mixture ⁇ NonI-HBA + NonI-HBD ⁇ is lower than the melting points of said NonI-HBD and NonI-HBA, considered separately.
  • the melting point of the mixture ⁇ NonI-HBA + NonI-HBD ⁇ or that of the eutectic composition is preferably below 50 °C, 40 °C, 30 °C, 20 °C, 10 °C or 0 °C.
  • the mixture ⁇ NonI-HBA + NonI-HBD ⁇ or the eutectic composition is preferably liquid at a temperature comprised between 0 °C and 50 °C, more preferably between 10 °C and 40 °C.
  • the mixture ⁇ NonI-HBA + NonI-HBD ⁇ represents more than 70 %, 80 %, 90 %, 95 %, 98 % or 99 % of the weight of the eutectic composition.
  • the molar ratio of the NonI-HBA to the NonI-HBD is comprised between 1/10 and 10/1, preferably between 1/3 and 2/1, more preferably between 4/10 and 6/10.
  • said molar ratio is 1/1 or 1/2, for instance 1/1.
  • the eutectic composition used in this invention may comprise several NonI- HBA / NonI-HBD pairs. In that situation, the molar ratio of the NonI-HBA to the NonI-HBD of each pair would be comprised within the aforesaid ranges.
  • the viscosity of the eutectic composition is such that it can be easily sprayed. In a particular embodiment, the viscosity of the eutectic composition is of at most 100 mPa.s at 25 (or at most 100 mPa.s at 20 °C).
  • the viscosity of the eutectic composition is comprised between 0.1 and 100 mPa.s at 25 °C (or between 0.1 and 100 mPa.s at 20 °C), more preferably between 0.1 and 20 mPa.s at 25°C (or between 0.1 and 20 mPa.s at 20°C).
  • the viscosity can be measured by using a rotary and oscillating rheometer, such as the MCR 51 rotary and oscillating rheometer from Anton Paar. In such a set-up, typically 1 to 2 mL of a liquid mixture is put on a surface and then put in contact with a cone coming down on the top of the surface, hence squeezing the liquid.
  • the NonI-HBA of the eutectic composition used in the present invention is a neutral (or “non- ionic”) compound that is able to form a hydrogen bond with a hydrogen atom of a non-ionic hydrogen bond donor, typically through its (or one of its) heteroatom(s), such as O or P.
  • the NonI-HBA of the eutectic composition used in the present invention is selected from the group consisting of a monoterpenoid, a phenyl propanoid, POR3 with each R being independently a C 1 -C 16 hydrocarbon group, 1-naphthol, phenethyl alcohol, C 1 -C 12 alkyl anthranilate, C 2 -C 12 alkenyl anthranilate, maltol and lidocaine.
  • the NonI-HBA is selected from a monoterpenoid, a phenyl propanoid, POR 3 with each R being independently a C 1 -C 16 hydrocarbon group, 1-naphthol, and lidocaine.
  • the NonI-HBA is a monoterpenoid.
  • the term “monoterpenoid” refers to a saturated or unsaturated, acyclic, monocyclic, or bicyclic compound which consists of a 10 carbon backbone (equivalent to 2 isoprene units) structure and advantageously has functional groups such as alcohols, aldehydes, and ketones.
  • monoterpenoids include, but are not limited to, citral, geraniol, lavandulol, linalool, terpineol, thymol, menthol, isomenthol, camphor, borneol, carvone, eucalyptol, and perillaldehyde.
  • menthol is DL-menthol.
  • carvone is L-carvone.
  • the NonI-HBA is a monoterpenoid selected from the group consisting of menthol, isomenthol, camphor, thymol, linalool, borneol, terpineol, geraniol, and carvone.
  • the NonI-HBA is a monoterpenoid chosen from menthol, isomenthol, thymol, terpineol, and carvone. Even more preferably, the NonI-HBA is menthol or isomenthol. In another particular embodiment, the NonI-HBA is a phenyl propanoid.
  • phenyl propanoid refers to an organic compound synthesized by plants from phenylalanine and tyrosine, having at least one phenyl moiety (typically one or two, preferably one) and functional groups such as alcohols, aldehydes, ketones, esters or ethers.
  • the phenyl propanoid has 6 to 16 carbon atoms.
  • phenyl propanoids include, but are not limited to, coniferyl alcohol, coumaryl alcohol, sinapyl alcohol, anethol, eugenol, chavicol, safrole, estragole, ethyl cinnamate, hydrocinnamic acid, coumarin, ombelliferone, or resveratrol.
  • the NonI-HBA is a phenyl propanoid selected from the group consisting of anethol and coumarin.
  • the NonI-HBA is POR 3 with each R being independently a C 1 -C 1 6 hydrocarbon group.
  • Said C 1 -C 1 6 hydrocarbon group may in particular be a C 1 -C 1 6 alkyl, preferably a C 4 -C 12 alkyl, more preferably a C 6 -C 10 alkyl.
  • a preferred POR 3 as defined herein is trioctylphosphine oxide.
  • the NonI-HBA is phenethyl alcohol.
  • the NonI-HBA is a C 1 -C 12 alkyl anthranilate or a C 2 -C 12 alkenyl anthranilate, preferably a C 1 -C 6 alkyl anthranilate or a C 2 -C 6 alkenyl anthranilate, more preferably methyl anthranilate.
  • the NonI-HBA is maltol.
  • the NonI-HBA is: - a monoterpenoid selected from the group consisting of menthol, isomenthol, camphor, thymol, linalool, borneol, terpineol, geraniol, and carvone, - a phenyl propanoid selected from the group consisting of anethol and coumarin, - trioctylphosphine oxide, - phenethyl alcohol, - methyl anthranilate, or - maltol More preferably, the NonI-HBA is: - a monoterpenoid selected from the group consisting of menthol, isomenthol, camphor, thymol, linalool, borneol, terpineol, and geraniol, - a phenyl propanoid selected from the group consisting of anethol and coumarin, - trioctylphosphine oxide.
  • the NonI-HBD of the eutectic composition used in the present invention is a neutral (or “non- ionic”) compound that is able to form a hydrogen bond with a heteroatom (such as O or P) of a non-ionic hydrogen bond acceptor, typically through its (or one of its) hydrogen atom.
  • the NonI-HBD of the eutectic composition used in the present invention is selected from the group consisting of C 6 -C 2 2 phenols, C 3 -C 2 2 carboxylic acids, monoterpenoids and phenylpropanoids.
  • the NonI-HBD of the eutectic composition used in the present invention is a C 6 -C 2 2 phenol.
  • a “C 6 -C 22 phenol” refers to a compound comprising a phenol scaffold (as shown below), and having 6 to 22 carbon atoms.
  • the phenol scaffold may be unsubstituted, or substituted by at least one substituent preferably selected from a C 1 -C 16 hydrocarbon group (such as C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 3 -C 16 cycloalkyl, or aryl), a halogen atom (e.g.
  • C 6 -C 22 phenols include, but are not limited to, phenol, salicylic acid, methyl salicylate, thymol, guaiacol, carvacrol, eugenol, chavicol, coniferyl alcohol, coumaryl alcohol, sinapyl alcohol, cresol, sesamol, gallic acid, or resveratrol.
  • Preferred C 6 -C 2 2 phenols are thymol and eugenol, more preferably thymol.
  • the NonI-HBD of the eutectic composition used in the present invention is a C 3 -C 2 2 carboxylic acid.
  • a “C 3 -C 22 carboxylic acid” refers to a compound comprising at least one (preferably one) -CO 2 H group and having 3 to 22 carbon atoms.
  • the C 3 -C 22 carboxylic acid may be aliphatic or aromatic, cyclic or acyclic, saturated or unsaturated.
  • the C 3 -C 2 2 carboxylic acid may be unsubstituted, or substituted by at least one substituent preferably selected from C 1 -C 16 hydrocarbon group (such as C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 3 -C 16 cycloalkyl, or aryl), a halogen atom (e.g. -I, -Br, -F, or -Cl), a hydroxyl group, -CN, -OR”, -SR”, -N(R”)2, -COR", - CO2R” with each R” being a hydrogen atom or C 1 -C 1 6 hydrocarbon group.
  • C 1 -C 16 hydrocarbon group such as C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 3 -C 16 cycloalkyl, or aryl
  • a halogen atom e.g. -I, -Br, -F, or
  • the C 3 -C 22 carboxylic acid may be levulinic acid, hydrocinnamic acid, acetylsalicylic acid, or a compound of formula R’-CO2H with R’ being C 3 -C 2 1 alkyl or C 3 -C 2 1 alkenyl.
  • the C 3 -C 2 2 carboxylic acid is a compound of formula R’-CO2H, with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkenyl.
  • R’ is a C 5 -C 17 alkyl or C 5 -C 17 alkenyl.
  • R’ is a C 9 -C 15 alkyl or C 9 -C 15 alkenyl.
  • R’-CO2H may be selected from naturally-occurring fatty acids, such as caprylic acid, capric acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, myristoleic acid, oleic acid, linoleic acid or arachidonic acid.
  • a preferred R’-CO2H is decanoic acid (i.e. R’ being C 1 0 alkyl), undecanoic acid (i.e. R’ being C 1 1 alkyl), or undecylenic acid (i.e.
  • R’ being C 11 alkenyl), more preferably undecanoic acid.
  • substituted carboxylic acids are levulinic acid, lactic acid and glycolic acid.
  • the NonI-HBD is selected from monoterpenoids and phenyl propanoids, such as those described above with respect to the NonI-HBA.
  • Preferred examples of monoterpenoids useful as NonI-HBD are camphor, borneol, sobrerol and menthol.
  • An example of phenyl propanoid useful as a NonI-HBD is coumarin or hydrocinnamic acid.
  • the NonI-HBD is selected from the group consisting of levulinic acid, hydrocinnamic acid, eugenol, coumarin, thymol, acetylsalicylic acid, and R’-CO2H with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkenyl (preferably: thymol, acetylsalicylic acid, and R’-CO 2 H with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkenyl).
  • the NonI-HBD may be a compound which is both a C 6 -C 2 2 phenol and a C 3 -C 2 2 carboxylic acid, or both a phenylpropanoid and a C 3 -C 22 carboxylic acid (such as hydrocinnamic acid).
  • a given compound may intrinsically be both a NonI-HBA and a NonI-HBD as defined herein, it is understood that the NonI-HBD and the NonI-HBA in the eutectic composition used in the present invention are different.
  • the NonI-HBA / NonI-HBD pair is selected from: menthol / R’-CO 2 H with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkenyl, isomenthol / R’-CO 2 H with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkenyl, trioctylphosphine oxide / acetylsalicylic acid, anethol / R’-CO 2 H with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkenyl, camphor / thymol, thymol / R’-CO2H with R’ being C 3 -C 2 1 alkyl or C 3 -C 2 1 alkenyl, anethol/hydrocinnamic acid, terpineol/ R’-CO 2 H with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkeny
  • the NonI-HBA / NonI-HBD pair is selected from: - menthol / R’-CO2H with R’ being C 3 -C 2 1 alkyl or C 3 -C 2 1 alkenyl, - isomenthol / R’-CO 2 H with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkenyl, - trioctylphosphine oxide / acetylsalicylic acid, - anethol / R’-CO2H with R’ being C 3 -C 2 1 alkyl or C 3 -C 2 1 alkenyl, - camphor / thymol, and - thymol / R’-CO 2 H with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkenyl.
  • a NonI-HBA / NonI-HBD pair is selected from: - menthol / R’-CO 2 H with R’ being C 3 -C 21 alkyl or C 3 -C 21 alkenyl, - isomenthol / R’-CO2H with R’ being C 3 -C 2 1 alkyl or C 3 -C 2 1 alkenyl.
  • the molar ratio of menthol or isomenthol to R’-CO2H is preferably comprised between 4:6 and 6:4.
  • the molar ratio of menthol or isomenthol to R’- CO2H may be 1:2.
  • Step (a) of the process of the present invention comprises contacting a eutectic composition as defined herein, with air, wherein said contacting is carried out by spraying said eutectic composition within said air.
  • spraying the eutectic composition refers to the nebulization of said composition, i.e. the dispersion of said composition, which is in a liquid state, so as to obtain a set of fine droplets (typically called a mist).
  • nebulization of the composition can be carried out by any techniques known to the skilled artisan, for instance by means of a mechanic or manual spray, a jet nebulizer, an aerosol containing a propellant, a piezoelectric or ultrasonic nebulizer.
  • “recovering a deodorized air” in step (b) means obtaining a deodorized air, after contacting said eutectic composition within said air according to the process of the invention.
  • the deodorized air obtained in step (b) refers to an air wherein the olfactive intensity of malodors is reduced with respect to the initial air of step (a).
  • the process of the invention is typically a process for reducing malodors within air.
  • the eutectic composition may intrinsically have its own odor, such that the deodorized air may have the odor of the eutectic composition.
  • the at least one malodor is chosen from hydrocarbon, alcohol, aldehyde, ester, ketone, ethers, amine, sulphur or acid odors.
  • the malodor is chosen from amine or ether odors.
  • hydrocarbon odors include, but are not limited to, benzene, toluene, xylene, ethylbenzene, hexane, cyclohexane, heptane, or dicyclopentadiene.
  • Examples of alcohol odors include, but are not limited to, isopropanol, isopentanol, butanol, or phenol.
  • Examples of aldehyde odors include, but are not limited to, nonanal, (E,E)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-decenal, butyraldehyde, or valeraldehyde.
  • Examples of ester odors include, but are not limited to, ethyl caproate.
  • ketone odors include, but are not limited to, diacetyl, heptan-2-one, 1-octen-3-one, 1-penten-3-one, or 2,3-butadione.
  • ether odors include, but are not limited to, furan derivatives such as 2-pentylfuran or furfuryl alcohol.
  • acid odors include, but are not limited to, isovaleric acid, butyric acid, acetic acid, propionic acid, or 2-methylbutanoic acid.
  • amine odors include, but are not limited to, pyridine, skatole, 2-acetylpyrazine, ammoniac, putrescine, diethylamine, trimethylamine, or cadaverine.
  • sulphur odors include, but are not limited to, dimethylsulfone, allyl isothiocyanate, hydrogen sulfide, dimethyldisulfide, benzyl mercaptan, dimethyl trisulfide, allyl disulfide, ethanethiol, propanethiol, butanethiol, or thiophenol.
  • the malodor is chosen from benzene, toluene, xylene, ethylbenzene, hexane, cyclohexane, heptane, dicyclopentadiene, isopropanol, isopentanol, butanol, phenol, nonanal, (E,E)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-decenal, butyraldehyde, valeraldehyde, ethyl caproate, diacetyl, heptan-2-one, 1-octen-3-one, 1-penten-3-one, 2,3- butadione, furan derivatives such as 2-pentylfuran or furfuryl alcohol, isovaleric acid, butyric acid, acetic acid, propionic acid, 2-methylbutanoic acid, pyridine, skatole, 2-ace
  • the malodor is chosen from dicyclopentadiene, isopropanol, isopentanol, butanol, nonanal, (E,E)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-decenal, butyraldehyde, valeraldehyde, ethyl caproate, diacetyl, heptan-2-one, 1-octen-3-one, 1-penten- 3-one, 2,3-butadione, furan derivatives such as 2-pentylfuran or furfuryl alcohol, isovaleric acid, acetic acid, 2-methylbutanoic acid, pyridine, skatole, 2-acetylpyrazine, ammoniac, putrescine, diethylamine, trimethylamine, cadaverine, dimethylsulfone, allyl isothiocyanate, hydrogen sulfide,
  • the malodor is chosen from, 2-pentylfuran, furfuryl alcohol, isovaleric acid, acetic acid, 2-methylbutanoic acid, pyridine, skatole, 2-acetylpyrazine, ammoniac, putrescine, diethylamine, trimethylamine, or cadaverine.
  • the malodor is chosen from cadaverine, diethylamine, 2- acetylpyrazine, allyl isothiocyanate, benzyl mercaptan, dimethyldisulfide, dimethylsulfone, nonanal, heptan-2-one, butyric acid, butanol, furfuryl alcohol, ethyl caproate, toluene, and heptane, preferably from cadaverine, diethylamine, 2-acetylpyrazine, allyl isothiocyanate, benzyl mercaptan, dimethylsulfone, nonanal, heptan-2-one, butanol, furfuryl alcohol, and ethyl caproate, more preferably from cadaverine, diethylamine, 2-acetylpyrazine, allyl isothiocyanate, and furfuryl alcohol.
  • the malodor is chosen from butanol, dimethyldisulfide, butyric acid, furfuryl alcohol, allyl isothiocyanate, heptan-2-one, 2-acetylpyrazine, ethyl caproate, benzyl mercaptan, and nonanal.
  • the eutectic composition may be used for deodorizing air from any source, such as air from a domestic (such as toilet, kitchen, or pet litter), commercial (such as a restaurant), or industrial environment.
  • the eutectic composition may be combined with a product which generates malodors.
  • the present invention also relates to a deodorizing product comprising a eutectic composition as defined herein, wherein said deodorizing product is a spray.
  • a “spray” denotes any device suitable to spray said eutectic composition, i.e. to nebulize the liquid eutectic composition into a mist.
  • the spray may be a mechanic or manual spray, a jet nebulizer, an aerosol containing a propellant, a piezoelectric or ultrasonic nebulizer.
  • the eutectic composition may be used in a diluted form.
  • Suitable solvents for diluting the eutectic composition include, but are not limited to ethanol or any organic solvent suitable with the application thereof.
  • the present disclosure also describes a use of a eutectic composition as defined herein as a deodorizing agent, typically for deodorizing air or a surface.
  • the eutectic composition may be used for removing any odors (or malodors) present within air or on a surface.
  • NonI-HBA non-ionic hydrogen bond acceptor
  • NonI-HBD non-ionic hydrogen bond donor
  • said NonI-HBA is selected from the group consisting of a monoterpenoid, a phenyl propanoid, POR3 with each R being independently a C 1 -C 1 6 hydrocarbon group, 1-naphthol and lidocaine
  • said NonI-HBD is selected from the group consisting of C 6 -C 22 phenols, C 3 -C 22 carboxylic acids, monoterpenoids and phenylpropanoids.
  • the eutectic composition is particularly advantageous in that it can provide both a deodorizing effect and a fragrancing effect, thus eliminating the need for additional perfumes in cosmetic products, for instance.
  • the present disclosure also describes a process for deodorizing air or a surface, comprising at least one malodor, said process comprising: (a) contacting a eutectic composition as defined herein with said air or surface comprising at least one malodor; and (b) recovering a deodorized air or surface.
  • the present disclosure also describes a process for deodorizing a surface comprising at least one malodor, said process comprising: (a) contacting a eutectic composition as defined herein with said surface comprising at least one malodor; and (b) recovering a deodorized surface.
  • Contacting in step (a) may in particular be carried out by applying (preferably spraying) a eutectic composition as defined herein on the surface.
  • the eutectic composition may be applied (for instance, sprayed) onto a surface.
  • the surface may be any material and may be a surface of any article.
  • the eutectic composition may for instance be applied or sprayed onto a textile, a non-woven material such as a baby diaper, tiles or an animal's hair or fur.
  • the surface is not a part of the human body or of an animal.
  • the deodorizing product comprising a eutectic composition as defined herein may be a spray, and could also be a candle, a fragrance diffuser, a cartridge or an impregnated material.
  • the eutectic composition may be used in a cartridge of an extractor hood.
  • the impregnated material may for instance be paper, cardboard, a tissue or a wipe.
  • the eutectic composition may be used as a deodorizing agent in a cosmetic product.
  • the cosmetic product may be, for instance, a deodorant, an anti-perspirant, a soap or a shampoo or other topic and hair formulations, comprising a eutectic composition as defined herein in a physiologically acceptable medium.
  • the deodorizing or cosmetic product can further comprise one or more components chosen according to the intended use.
  • Such components include the above solvents; surfactants; aqueous phase gelling agents; oily phase thickeners; preservatives; antioxidants; chelating agents; polyols; odor absorbers such as zeolites, cyclodextrins, silica, aluminosilicates or activated carbon; UV absorbers; antimicrobial agents; perfumes such as essential oils; pigments; and dyes, this list being not limitative, provided that these constituents do not harm the deodorizing properties of the eutectic composition.
  • the eutectic composition can moreover be conveyed in microspheres, nanocapsules, microcapsules, liposomes or any other vector allowing its incorporation into the deodorizing or cosmetic product.
  • the incorporation of the eutectic composition into the deodorizing or cosmetic product can in particular be made by mixing the eutectic composition and said further components.
  • the present disclosure also describes a process for deodorizing air comprising at least one malodor, said process comprising: (a) contacting a eutectic composition as defined herein with said air; and (b) recovering a deodorized air, wherein contacting in step (a) is carried out by passing the air through a eutectic composition as defined herein.
  • air may have a flow rate comprised between 100 m 3 /h and 10000 m 3 /h.
  • Example 1 Use of a eutectic composition for purifying a gaseous phase – Experiment in a vial 20 ⁇ L of a smelly solution having the following composition: 50 ⁇ L butanol + 50 ⁇ L butyric acid + 50 ⁇ L dimethyldisulfide + 50 ⁇ L allyl isothiocyanate + 50 ⁇ L furfuryl alcohol + 50 ⁇ L 2-acetypyrazine + 50 ⁇ L ethyl caproate + 25 ⁇ L heptan-2-one + 50 ⁇ L benzylmercaptan + 50 ⁇ L nonanal, were injected into a 40 mL headspace vial.
  • Table 1 Water, used as a control, does not neutralize the malodorous compounds besides butanol, butyric acid, furfuryl alcohol and ethyl caproate, which are water-soluble compounds. Febreze ® eliminates the same compounds as water, with slightly higher yields. Compositions A and B are more than 90% effective against the majority of malodorous compounds. Compositions of the invention can therefore be used for a variety of malodorous molecules and eliminate those in high yields. Example 2.
  • a eutectic composition for purifying a gaseous phase – Experiment in a vial 2 ⁇ L of a smelly solution having the following composition: 50 ⁇ L butanol + 50 ⁇ L butyric acid + 50 ⁇ L dimethyldisulfide + 50 ⁇ L allyl isothiocyanate + 50 mg 2-acetypyrazine + 50 ⁇ L ethyl caproate + 25 ⁇ L heptan-2-one + 50 ⁇ L benzylmercaptan + 50 ⁇ L nonanal, were injected into a 40 mL headspace vial. The solution was stirred at 300 rpm and heated to 70 °C for one hour, and then cooled to room temperature without stirring for 30 minutes.
  • HS-SPME fiber 50/30 ⁇ m DVB / CAR / PDMS
  • the SPME fiber was exposed for 2 minutes in the atmosphere of the vial and then desorbed and analyzed by GC - MS / FID. This exposure time was previously validated by varying the exposure time of the SPME fiber in the gas phase, and checking that 2 minutes allowed good reproducibility of the analyzes.
  • 2 mL of a eutectic composition of the invention were injected using a syringe into the vial.
  • N.T. means « Not tested Colour Example 3.
  • a filter paper was impregnated with 20 ⁇ L of the smelly solution described in Example 1 and then placed under a 17 L airtight chamber, in which was present a fan (imitating an air flow as in the atmosphere). After 1 hour, time necessary to charge the gas phase with odors and ensure a constant concentration of gas-phase odors, a first SPME extraction (same fiber as in Example 1). The fiber was exposed via a septum to the gas phase of the chamber for 4 minutes, then analyzed by GC / FID.
  • the chromatogram obtained shows the quantity of odors initially present in the gas phase, and represents the control before neutralization (Figure 3). It was established beforehand that between 1 and 4 hours after the introduction of the impregnated filter paper into the chamber, the chromatogram is substantially constant, demonstrating that the concentration of the odors in the gas phase does not vary.
  • 2 g of a eutectic composition of the invention was sprayed using a manual sprayer into the chamber ( Figure 2). 15 seconds later, a second 4-minute SPME extraction was performed.
  • the analysis of the SPME fiber by GC / FID provided another chromatogram, allowing to determine an odor elimination yield according to equation 1. Each analysis was carried out in triplicate.
  • Composition A extracted up to 71% of butyric acid, followed by 68 and 63% nonanal and ethyl caproate respectively.
  • Composition B is even more effective, since it neutralizes 95% of butyric acid, followed by 84 and 71% of ethyl caproate and nonanal respectively.
  • Example 4 Use of a eutectic composition for purifying a gaseous phase – Experiment in chamber A filter paper was impregnated with 20 ⁇ L of the smelly solution described in Example 1 and then placed under a 17 L airtight chamber.
  • the impregnated filter paper is removed from the chamber and a first SPME extraction (same fiber as in Example 1). The fiber was exposed via a septum to the gas phase of the chamber for 4 minutes, then analyzed by GC / MS / FID. The chromatogram obtained shows the quantity of odors initially present in the gas phase, and represents the control before neutralization. It was established beforehand that between 1 and 4 hours after the introduction of the impregnated filter paper into the chamber, the chromatogram is substantially constant, demonstrating that the concentration of the odors in the gas phase does not vary.
  • the goal of this experiment was to evaluate the viscosity of the eutectic compositions. Measurements were performed with Physica MCR 51 (Anton Paar) rotary and oscillating viscometer. Plate/Plate PP-50 (Anton Paar) measuring system was used with a rotor-stator gap of 0.048mm. RheoPlus software was used to record and evaluate the measurement results. The measurement profile was recorded by the software to increase the shear rate from 475 s -1 to 8000 s -1 during the 185 second measurement time, while taking the measurement points every 5 seconds. Samples were tested at 20°C. The temperature was maintained with a P-PTD200 Peltier Temperature Device. These results show that the eutectic compositions according to the invention have a low dynamic viscosity which make them suitable for vaporization/nebulization in the air/atmosphere.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)

Abstract

La présente invention concerne un procédé de désodorisation d'air par pulvérisation d'une composition eutectique comprenant un accepteur de liaison hydrogène non ionique et un donneur de liaison hydrogène non ionique, à l'intérieur dudit air. L'invention concerne également un produit désodorisant comprenant ladite composition eutectique.
PCT/EP2021/071440 2020-07-31 2021-07-30 Eutectiques profonds hydrophobes non ioniques en tant qu'agent désodorisant WO2022023547A1 (fr)

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Cited By (1)

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CN114314726A (zh) * 2020-09-27 2022-04-12 广州中国科学院沈阳自动化研究所分所 一种疏水性低共熔溶剂及其在萃取工业含酚废水中的应用

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US5891427A (en) * 1996-04-08 1999-04-06 Mettler; Leo Vitaminized air freshner and room deodorizer
US6090774A (en) * 1998-10-13 2000-07-18 International Flavors & Fragrances Inc. Single phase liquid mixture of benzophenone and mixture of at least two other normally solid perfumery substances and perfumery uses thereof
JP2007014749A (ja) * 2005-06-07 2007-01-25 Kao Corp 消臭剤組成物
US8298553B2 (en) * 2007-12-06 2012-10-30 Conopco, Inc. Personal care composition
US20150297484A1 (en) * 2012-12-20 2015-10-22 Conopco, Inc., D/B/A Unilever Eutectic mixtures in personal care compositions
US9351944B1 (en) * 2008-11-07 2016-05-31 Takasago International Corporation Malodor eliminating compositions
WO2018091379A1 (fr) 2016-11-18 2018-05-24 Universite Du Littoral Cote D'opale Procédé d'épuration d'un effluent gazeux
US20200163334A1 (en) * 2016-02-29 2020-05-28 Fmc Corporation Insect repellent

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5891427A (en) * 1996-04-08 1999-04-06 Mettler; Leo Vitaminized air freshner and room deodorizer
US6090774A (en) * 1998-10-13 2000-07-18 International Flavors & Fragrances Inc. Single phase liquid mixture of benzophenone and mixture of at least two other normally solid perfumery substances and perfumery uses thereof
JP2007014749A (ja) * 2005-06-07 2007-01-25 Kao Corp 消臭剤組成物
US8298553B2 (en) * 2007-12-06 2012-10-30 Conopco, Inc. Personal care composition
US9351944B1 (en) * 2008-11-07 2016-05-31 Takasago International Corporation Malodor eliminating compositions
US20150297484A1 (en) * 2012-12-20 2015-10-22 Conopco, Inc., D/B/A Unilever Eutectic mixtures in personal care compositions
US20200163334A1 (en) * 2016-02-29 2020-05-28 Fmc Corporation Insect repellent
WO2018091379A1 (fr) 2016-11-18 2018-05-24 Universite Du Littoral Cote D'opale Procédé d'épuration d'un effluent gazeux

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114314726A (zh) * 2020-09-27 2022-04-12 广州中国科学院沈阳自动化研究所分所 一种疏水性低共熔溶剂及其在萃取工业含酚废水中的应用

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