Method for reducing malodour using cucurbituril

Abstract

To provide a method for reducing malodour and a solid composition.SOLUTION: Provided is a method comprising the step of preparing a solid composition comprising one or more cucurbiturils and derivatives and / or analogues thereof suspended in and / or bound by a thermoplastic and / or a thermosetting polymer medium, wherein the source of the malodour is external.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a method for reducing malodors, in particular a method for reducing malodors, comprising the step of providing a solid composition comprising one or more cucurbiturils and derivatives and / or analogues thereof suspended in and / or bound by a thermoplastic and / or thermosetting polymer medium, wherein the source of the malodors is external. [Background technology]

[0002] WO 2017 / 141029 (Aqdot Limited) discloses the use of a composition containing a mixture of two or more cucurbiturils selected from cucurbit[5]uril, cucurbit[6]uril, cucurbit[7]uril, and cucurbit[8]uril to counteract malodors in humid environments. The terms cucurbit[5]uril, cucurbit[6]uril, cucurbit[7]uril, and cucurbit[8]uril refer to cucurbituril molecules formed from five, six, seven, and eight glycoluril molecules, respectively. The composition may contain additives selected from preservatives, dyes, pigments, sequestering agents, and antioxidants, and may be provided in various forms, including adsorbed onto a substrate such as a fabric. Cucurbiturils may also be added to products such as consumer products for laundry, home, or personal care, where the product is in the form of a powder or granule, tablet or unit dose, dispersion, emulsion, microemulsion, solution, hydroalcoholic product, wipe, sponge, aerosol or liquid dispenser, cream, balsam, polish, wax, etc. The consumer product may be, among other things, an air freshener or air filtration device.

[0003] WO 2018 / 037209 (Aqdot Limited) discloses a stable suspension composition comprising cucurbituril particles suspended in a medium. The medium can be a wax. The composition can further comprise a suspending agent selected from a number of polymers, such as polyvinyl alcohol. The composition can further comprise additives selected from the group consisting of surfactants, biocides, thickeners, antioxidants, chelating agents, humectants, deposition agents, foam suppressants, fragrances, solvents, dyes, pigments, antiperspirants, and conditioning agents. The composition can form part of the consumer products described above, including candles, in the form of powders or granules, tablets or single-dose units, wipes, sponges, compressed gas, aerosol, or liquid dispensers, creams, balsams, polishes, waxes, and the like. The compositions of WO 2018 / 037209 can also be applied to inanimate surfaces, such as kitchen or bathroom surfaces, or to the surface of granules or beads.

[0004] WO 2016 / 185209 (Aqdot Limited) discloses an epoxy composition containing a cucurbituril complexed to a curing agent. Thus, in one example, a composition containing the curing agent 1,4-diaminobutane, at least partially complexed with cucurbit[8]uril, and bisphenol A diglycidyl ether exhibited a slower cure rate upon storage than a comparable composition without cucurbit[8]uril, i.e., was more stable.

[0005] US Patent Application No. 2018 / 0247632 (Henkel AG & Co., KGAA) discloses a hot melt composition suitable for damping applications, preferably sound deadening applications, that has low volatile organic compound emissions at application temperatures, the hot melt composition comprising a poly-α-olefin, an elastomeric styrene-based copolymer, a tackifier, and a macrocycle. The macrocycle may be selected from cyclodextrins, calixarenes, and cucurbiturils. In one example, a C3 / C2 poly-α-olefin, a styrene-isopropyl copolymer, and a tackifier are used. A composition containing ethylene-styrene copolymer, alkylphenol resin (a tackifier), graphite filler, and β-cyclodextrin was demonstrated to emit fewer volatile organic compounds from the product at 100°C in a "fogging test" than a comparative composition without β-cyclodextrin. Summary of the Invention [Problem to be solved by the invention]

[0006] Therefore, there remains a need to provide a method for reducing malodors, comprising the step of preparing a solid composition, wherein the malodor source is external, particularly wherein the solid composition comprises cucurbituril and / or its derivatives and / or analogs, and wherein the solid composition is in the form of an isolated film or a coating attached to an inanimate surface. Surprisingly, it has been observed that cucurbituril retains its ability to reduce malodors from external sources, even when suspended in a thermoplastic and / or thermosetting polymer medium. Furthermore, the presence of a thermoplastic and / or thermosetting polymer medium reduces or eliminates the technical problem of dusting cucurbituril particulate powder. [Means for solving the problem]

[0007] In a first aspect of the present invention, there is provided a method for reducing malodour, comprising the step of providing a solid composition comprising one or more cucurbiturils and derivatives and / or analogues thereof suspended in and / or bound by a thermoplastic and / or thermosetting polymer medium, wherein the source of the malodour is external.

[0008] As used herein, the term "malodor" refers to unpleasant or unwanted odors frequently encountered in daily life and have a variety of origins. Typical malodors include odors emanating from uncontrolled industrial activities, cleaning agents, including disinfectants, human and pet body odors such as sweat and excretions, kitchen odors (including, but not limited to, food and beverages) and food processing, cigarette smoke, and mold. Some of the most bothersome malodors for humans are sweat, feces, urine, wet pets, cooking odors, especially garlic, cabbage, fish, and onions. Malodors can also emanate from fatty acids and fatty acid derivatives present in consumer products, such as soaps, detergents, shampoos, and conditioners. Another example of a particularly undesirable malodor is the malodor caused by hair removal creams (sulfur compounds). All of these malodors are particularly irritating.

[0009] The malodor to be reduced may be caused by a mixture of malodor-causing molecules. The malodor is reduced by a solid composition comprising one or more cucurbiturils and derivatives and / or analogs thereof.

[0010] Malodor reduction is achieved by complexing the malodor-causing molecule with one or more cucurbiturils and their derivatives and / or analogues. As used herein, the term "solid" means a solid at a temperature up to at least 80°C, preferably at least 100°C, more preferably at least 120°C, and for thermoplastic polymers, a solid having a glass transition temperature of at least 80°C, preferably at least 100°C, more preferably at least 120°C.

[0011] In the context of this specification, the term "bound by" means that, in the context of the present invention, one or more cucurbiturils and derivatives and / or analogs thereof are bound together by a thermoplastic and / or thermosetting polymer medium, but are not necessarily suspended therein. Thus, in one embodiment, one or more cucurbiturils and derivatives and / or analogs thereof may protrude from the thermoplastic and / or thermosetting polymer medium. In another embodiment, one or more cucurbiturils, typically in the form of particles, may protrude from the thermoplastic and / or thermosetting polymer medium. The uril and its derivatives and / or analogues are in the form of particles agglomerated together.

[0012] As used herein, the term "external" means outside the solid composition. Thus, the solid composition itself is not the source of the malodor. In a second aspect of the present invention, there is provided a solid composition comprising one or more cucurbiturils and derivatives and / or analogues thereof suspended in and / or attached by a thermoplastic and / or thermosetting polymer medium, and further comprising one or more fragrance molecules.

[0013] In a third aspect of the present invention, there is provided a solid composition comprising one or more cucurbiturils and derivatives and / or analogues thereof bound by a thermoplastic and / or thermosetting polymeric medium, wherein when the solid composition is in the form of a coating or aggregate attached to an inanimate surface, the composition comprises more than 10% w / w, preferably more than 25% w / w, more preferably at least 50% w / w, more preferably at least 75% w / w of the one or more cucurbiturils and derivatives and / or analogues thereof and optionally one or more carbon black and / or inorganic pigments and / or extenders, and preferably no more than 95% w / w, more preferably no more than 98% w / w, most preferably no more than 99% w / w of the one or more cucurbiturils and derivatives and / or analogues thereof and optionally one or more carbon black and / or inorganic pigments and / or extenders, wherein the solid composition comprises at least an effective amount of one or more cucurbiturils and derivatives and / or analogues thereof.

[0014] The invention will now be described with reference to the drawings identified below. [Brief explanation of the drawings]

[0015] [Figure 1] Figure 1 shows the reduction in n-butyric acid concentration (R) (%) compared to the control (cardboard or sponge substrate, or n-butyric acid) versus the mass (g) of mixed (unsubstituted) cucurbituril (PVOH = polyvinyl alcohol, LMW = low molecular weight, HMW = high molecular weight, CB = cucurbituril, paper = cardboard). [Figure 2] Figure 1 shows the reduction in n-butyric acid concentration (R) (% / g) compared to the control (cardboard or sponge substrate, or n-butyric acid) versus the mass (g) of the mixed (unsubstituted) cucurbituril, divided by the mass of the mixed (unsubstituted) cucurbituril (PVOH = polyvinyl alcohol, LMW = low molecular weight, HMW = high molecular weight, CB = cucurbituril, paper = cardboard). DETAILED DESCRIPTION OF THE INVENTION

[0016] In one aspect of the present invention, there is provided a method for reducing malodor, comprising the step of providing a solid composition comprising one or more cucurbiturils and derivatives and / or analogues thereof suspended in and / or bound by a thermoplastic and / or thermosetting polymer medium, wherein the source of the malodor is external.

[0017] To prepare the solid compositions of the first, second, and third aspects of the present invention, typically pellets or particulate powders of thermoplastic and / or one or more thermosetting polymer precursors are mixed with one or more cucurbiturils and / or derivatives and / or analogs thereof in the form of particulate powders or agglomerated particles at room temperature (typically 20-25°C) and atmospheric pressure. In one embodiment, a liquid solvent or carrier such as cyclohexane or water can be added along with optional excipients such as pigments, fillers such as talc or diatomaceous earth, dispersants, adhesion promoters, and biocides to form a liquid coating or paint, which can then be applied to an inanimate surface. The thermosetting precursors include a crosslinker added to crosslink other thermosetting polymer precursors, thereby forming a network. Alternatively, the thermoplastic and / or one or more cucurbiturils can be mixed with one or more cucurbiturils .... The thermosetting polymer precursor and one or more cucurbiturils and their derivatives and / or analogs are prepared separately in a liquid solvent or carrier and then combined to form a liquid coating or paint. In one embodiment, one or more crosslinkers and other thermosetting polymer precursors are prepared separately and then combined to form a liquid coating or paint. The coating or paint must be liquid at the application temperature and can be applied to an inanimate surface by any suitable method, including, but not limited to, spraying, brushing, rolling, dipping, or roll-to-roll coating. The liquid solvent or carrier is then evaporated at atmospheric pressure, either at room temperature or at an elevated temperature (above room temperature), thereby producing a solid composition of the present invention. Typically, elevated temperature or irradiation, such as ultraviolet light or an electron beam, is required to cure one or more thermosetting polymer precursors.

[0018] As used herein, the term "liquid" means liquid at temperatures above 5°C and below 400°C, 300°C, 250°C, 200°C, 150°C, more preferably below 100°C. In another embodiment, the preparation of the solid compositions of the first, second, and third aspects of the present invention does not involve a liquid solvent or carrier. In this embodiment, a mixture of thermoplastic and / or one or more thermosetting polymer precursors mixed with one or more cucurbiturils and their derivatives and / or analogs may be coated onto an inanimate surface by electrostatic forces, for example, using powder coating or fluidized bed techniques, or may be passed through a die to provide the desired final shape, for example, to form an isolated film. Elevated temperatures (above room temperature) are required to cure the one or more thermosetting polymer precursors and condense any surface coating, whether based on a thermoplastic or thermosetting polymer medium, or to process the mixture through a die. For thermoplastic polymers, the elevated temperature must be at least above the glass transition temperature, preferably above the melting temperature of the polymer. If the solid composition is in the form of an isolated film, the film may then be laminated onto an inanimate surface.

[0019] It has been observed that mixtures of thermoplastic polymers mixed with one or more cucurbiturils and their derivatives and / or analogs to form isolated films preferably contain less than 10% w / w, 7% w / w, 5% w / w, 2% w / w, 1% w / w of water to reduce the number of holes that appear in the resulting isolated film due to evaporation of water.

[0020] The preparation of solid compositions of the first, second and third aspects of the invention in the form of aggregates is described in Example 3. Preferably, the cucurbituril is selected from the group consisting of cucurbit[5]uril, cucurbit[6]uril, cucurbit[7]uril, cucurbit[8]uril, and mixtures thereof. Derivatives of cucurbituril are structures having one, two, three, four, or more substituted glycoluril units. Substituted cucurbituril compounds have the following structure:

[0021] [ka]

[0022] wherein n is an integer from 4 to 20, and in each glycoluril unit, each X is O, S, or NR 3 and -R 1 and -R 2 is -H and the following optionally substituted groups: -R 3 , -OH, -OR 3 , -COOH, -COOR 3 , -NH2, -NHR 3 and -N(R 3 )2, each independently selected from -R 3 is C 1~20 Alkyl, C 6~20 Carboaryl and C 5~20 heteroaryl, or -R 1 and / or -R 2 is -N(R 3 )2 and both -R 3 Let's get together and C 5~7 forming a heterocyclic ring, or -R 1 and -R 2 together with the uracil skeleton to form C 6~8 Forms a carbocyclic ring, C 4~6 alkylene] It can be represented by:

[0023] In one embodiment, one of the glycoluril units is a substituted glycoluril unit. 1 and -R 2 are each independently -H in n-1 of the glycoluril units. In one embodiment, n is 5, 6, 7, 8, 9, 10, 11, or 12. In one embodiment, n is 5, 6, 7, or 8. In one embodiment, each X is O. In one embodiment, each X is S. In one embodiment, R 1 and R 2 are each independently H.

[0024] In one embodiment, in each unit, R1 and R 2 is H, and the other is -H and the following optionally substituted group -R 3 , -OH, -OR 3 , -COOH, -COOR 3 , -NH2, -NHR 3 and -N(R 3 )2. In one embodiment, in one unit, R 1 and R 2 is H, and the other is -H and the following optionally substituted group -R 3 , -OH, -OR 3 , -COOH, -COOR 3 , -NH2, -NHR 3 and -N(R 3 )2. In this embodiment, the remaining glycoluril units are independently selected from R 1 and R 2 are each independently H.

[0025] Preferably, -R 3 is C 1~20 Alkyl, most preferably C 1~6 It is an alkyl. C 1~20 The alkyl group can be linear and / or saturated. Each group -R 3 may be independently unsubstituted or substituted. Preferred substituents are -R 4 , -OH, -OR 4 , -SH, -SR 4 , -COOH, -COOR 4 , -NH2, -NHR 4 and -N(R 4 )2, where -R 4 is C 1~20 Alkyl, C 6~20 Carboaryl and C 5~20 The substituents are selected from -COOH and -COOR. 4 can be independently selected from

[0026] In some embodiments, -R 4 Ha-R 3In some embodiments, -R 4 is preferably unsubstituted. -R 1 and / or -R 2 -OR 3 , -NHR 3 or -N(R 3 )2, then -R 3 is preferably C 1~6 In some embodiments, -R 3 is the substituent -OR 4 , -NHR 4 or -N(R 4 )2. Each -R 4 is C 1~6 It is alkyl, preferably itself substituted.

[0027] A cucurbituril variant may include a structure having one or more repeating units structurally similar to glycoluril. The repeating units may include ethylurea units. When all units are ethylurea units, the variant is a hemicucurbituril, for example, hemicucurbit

[12] uril:

[0028] [ka]

[0029] is. Preferably, the concentration of cucurbit[5]uril is from about 0 to about 99% by weight, more preferably from about 0.1 to about 75% by weight, more preferably from about 0.5 to about 50% by weight, more preferably from about 1 to about 30% by weight, more preferably from about 1 to about 25% by weight, and more preferably from about 1 to about 20% by weight, based on the total weight of cucurbituril in the composition.

[0030] Preferably, the concentration of cucurbit[6]uril is from about 0.1 to about 99% by weight, more preferably from about 1 to about 75% by weight, more preferably from about 5 to about 60% by weight, more preferably from about 20 to about 55% by weight, and more preferably from about 35 to about 55% by weight, based on the total weight of cucurbituril in the composition.

[0031] Preferably, the concentration of cucurbit[7]uril is from about 0.1 to about 99% by weight, more preferably from about 5 to about 75% by weight, more preferably from about 10 to about 60% by weight, and more preferably from about 20 to about 45% by weight, based on the total weight of cucurbituril in the composition.

[0032] Preferably, the concentration of cucurbit[7]uril is less than 45% by weight, based on the total weight of cucurbituril in the composition. Preferably, the concentration of cucurbit[8]uril is from about 0.1 to 99% by weight, more preferably from about 0.5 to about 75% by weight, more preferably from about 1 to about 30% by weight, more preferably from about 5 to about 25% by weight, and more preferably from about 10 to about 20% by weight, based on the total weight of cucurbituril in the composition.

[0033] Preferably, the total concentration of cucurbit[5]uril, cucurbit[6]uril, cucurbit[7]uril and cucurbit[8]uril in the composition is greater than 75% by weight, more particularly greater than about 90% by weight, more particularly greater than about 99% by weight, based on the total weight of cucurbiturils in the composition.

[0034] Preferably, the composition contains 1-17 wt.% cucurbit[5]uril, 30-50 wt.% cucurbit[6]uril, 20-37 wt.% cucurbit[7]uril, 10-27 wt.% cucurbit[8]uril, and less than 1 wt.% cucurbit[4]uril, cucurbit[9]uril, and / or higher molecular weight cucurbiturils, based on the total weight of cucurbiturils in the composition.

[0035] Typical malodor-causing molecules are preferably allylamine; methylamine; ethylamine; cyclobutylamine (cyclobutanamine, urinary); cyclopentylamine (cyclopentanamine); cyclohexylamine (cyclohexanamine); cycloheptylamine (cyclobutanamine); isopropylamine; butylamine; dibutylamine (N-butyl-1-butanamine); dimethylethanolamine (2-(dimethylamino)ethanol); methylethanolamine (2-(methylamino)ethanol); diethylethanolamine (2-(diethylamino)ethanol); diethylamine (N-methylethanamine, fishy); dipropylamine (N-propyl-1-propanamine); diisopropylamine (N-isopropyl-2-propanamine), dimethylacetamide (N,N-dimethylacetamide); ethylmethylamine (N-methylethanamine); ethylpropylamine (N-ethylpropanamide); trimethylamine (fishy); triethylamine amine (fishy); ethylenediamine (1,2-ethanediamine, musty, ammonia); propylenediamine (1,3-propanediamine); tetramethylenediamine (1,4-butanediamine, putrescine, nasty); ethyleneimine (aziridine, ammonia); morpholine (fishy); ethylmorpholine (4-ethylmorpholine, sour); pyrrolidine (semen); methylethylpyridine (2-ethyl-3-methylpyridine); pyridine (burnt, nauseating); vinylpyridine (4-vinylpyridine, nauseating); skatole (3-methylindole, feces); indole (feces); cadaverine (pentane-1,5-diamine, putrefaction); hydrogen sulfide (rotten eggs); allyl disulfide (3-(allyldisulfanyl)-1-propene, garlic); ethyl isothiocyanate (isothiocyanatoethane, pungent, mustard, nicotine) Garlic; allyl isothiocyanate (3-isothiocyanatoprop-1-ene, sulfur); allyl mercaptan (2-propene-1-thiol, garlic, sulfur); allyl sulfide (3-(allylsulfanyl)-1-propene; sulfur); diallyl sulfide (3-(allylsulfanyl)-1-propene; sulfur); dimethyl disulfide ((methylsulfanyl)ethane, unpleasant, garlic); dimethyl trisulfide (dimethyl trisulfane, unpleasant); diethyl sulfide ((ethylsulfanyl)ethane, sulfur); butyl sulfide (1-(butylsulfanyl)butane, garlic, violet); diethyl trisulfide (diethyl trisulfane, unpleasant, garlic); ethyl methyl disulfide ((methylsulfanyl)ethane, sulfur); phenyl sulfide (1,1'-sulfanediyldibenzene, sulfur); ethyl mercaptan ( Nitrogen- and sulfur-containing molecules selected from the group consisting of 1-ethanethiol, sulfur; amyl mercaptan (1-pentanethiol); isoamyl mercaptan (3-methylbutane-1-thiol, sulfur, onion); butyl mercaptan (1-butanethiol, skunk-like); isobutyl mercaptan (2-methylpropane-1-thiol, sulfur, mustard); dodecyl mercaptan (1-dodecanethiol); carbon disulfide (methanedithione, unpleasant, sweet); dimethyl trithiocarbonate (dimethyl carbonotrithioate); and thiophenol mercaptan; Oxygen-containing five-membered ring molecules, preferably selected from the group consisting of sotolone and norsotolone; saturated and unsaturated alkyl and hydroxyalkyl carboxylic acids, preferably selected from the group consisting of acetic acid, propionic acid, butyric acid, isovaleric acid, n-valeric acid, 2-methyl-butyric acid, 3-methyl-2-hexanoic acid, and 3-methyl-3-hydroxyhexanoic acid; and Cedryl acetate and naphthalene may be selected from:

[0036] Preferably, the thermoplastic medium is selected from the group consisting of linear low density polyethylene, low density polyethylene, medium density polyethylene, high density polyethylene, polyethylene, polypropylene, polyester, polyethylene terephthalate, polyacrylate homo- and copolymers, polymethacrylate homo- and copolymers, poly(methyl methacrylate), poly(acrylonitrile butadiene styrene), polyamide, poly(lactic acid), poly(benzimidazole), polycarbonate, poly(ether sulfone), poly(oxymethylene), poly(ether ether ketone), poly(ether imide), polystyrene, polyvinyl chloride, polyvinylidene fluoride, polytetrafluoroethylene, cellulose, polysaccharides, polyvinyl alcohol, polyvinyl acetate, partially hydrolyzed polyvinyl acetate, polyvinylpyrrolidone, and mixtures thereof.

[0037] Preferably, the thermosetting medium is selected from the group consisting of polyurethanes, polyurea-polyurethane hybrids, vulcanized rubbers, polyacrylates, polymethacrylates, phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins, epoxy resins, benzoxazines and hybrids of epoxy and phenolic resins with benzoxazines, polyimides, polybismaleimides, cyanate ester resins, furan resins, silicone resins, vinyl ester resins, alkyd resins, and mixtures thereof.

[0038] Advantageously, the composition further comprises one or more fragrance molecules. In particular and in a second aspect of the present invention, there is provided a solid composition comprising one or more cucurbiturils and derivatives and / or analogues thereof suspended in a thermoplastic and / or thermosetting polymer medium, and further comprising one or more fragrance molecules.

[0039] Common fragrance molecules include alcohols, aldehydes, ketones, lactones and O-heterocycles, ethers, acetals, ketals, N- and S-compounds, hydrocarbons and terpenes, and essential oils. Typical fragrance molecules include (Z)-4-dodecenal (21944-98-9); 1-octen-3-ol (3391-86-4); 2,6-nonadienol (28069-72-9); 2-isobutyl-3-methoxypyrazine (24683-00-9); 2-nonenal (2463-53-8); 2-undecenal (2463-77-6); trans-4-decenal (65405-70-1); 8-decen-5-olide (32764-98-0); 9-decenol (13 019-22-2); acetaldehyde, phenethyl propyl acetal (7493-57-4); 2,6,10-trimethylundec-9-enal (141-13-9); 10-undecenal (112-45-8); 2-methylundecanal (110-41-8); allyl amyl glycolate (67634-00-8); allyl hexanoate (123-68-2); allyl phenoxyacetate (7493-74-5); α-amyl cinnamaldehyde (122-40-7); α-Damascone (43052-87-5); 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1h-benzo[e][1]benzofuran (6790-58-5); 2-benzylideneheptanal (122-40-7); 1-(2-tert-butylcyclohexyl)oxybutan-2-ol (139504-68-0); amyl salicylate (2050-08-0); anisaldehyde diethyl acetal (2403-58-9); anisaldehyde Dehyde (123-11-5); benzaldehyde (100-52-5); benzyl acetate (140-11-4); β-naphthyl methyl ether (93-04-9); ethyl 6-(acetyloxy)hexanoate (104986-28-9); β-damascone (23726-92-3); β-ionone (14901-07-6); 4-t-butylbenzenepropionaldehyde (18127-01-0); 8-methyl-1,5-benzodioxepin-3-one (28940-11-6 35783-05-2);3-Methyl-5-propylcyclohex-2-en-1-one (3720-16-9); cis-3-hexen-1-ol (928-96-1); cis-6-nonenal (2277-19-2); citral (5392-40-5); citronellal (106-23-0); citronellol (106-22-9); citronellyloxyacetaldehyde (7492-67-3); dodecanenitrile (2437-25-4); coumadin Phosphorus (91-64-5); 2,6-Nonadien-1-ol (7786-44-9); Damascenone (23726-93-4); 2-Pentylcyclopentanone (4819-67-4); δ-Damascone (57378-68-4); Dihydromyrcenol (18479-58-8); Dimethylbenzylcarbinyl acetate (151-05-3); Diphenyl ether (101-84-8); 4-(octahydro-4,7-methano-5 h-Inden-5-ylidene)butanal (30168-23-1); 1-(5,5-dimethyl-1-cyclohexenyl)pent-4-en-1-one (56973-85-4); (z)-3-methyl-5-(2,2,3-trimethyl-1-cyclopent-3-enyl)pent-4-en-2-ol (67801-20-1); Ethyl 2-methylbutyrate (7452-79-1); Ethyl 2-methylpentanoate (39255 -32-8; ethyl butyrate (105-54-4); ethyl n-ethylanthranilate (38446-21-8); ethyl trans-2,cis-4-decadienoate (3025-30-7); ethyl vanillin (121-32-4); ethyl vinyl ketone (1629-58-9); eucalyptol (470-82-6); eugenol (97-53-0); methyl 2,4-dihydroxy-3,6-dimethylbenzoate; Farnesene (alpha and beta) (502-61-4); Fixolide (1506-02-1); Tricyclodecenylpropionate (68912-13-0); 3-(3-propan-2-ylphenyl)butanal (125109-85-5); 2-butan-2-ylcyclohexan-1-one (14765-30-1); Ethyl 2-(2-methyl-1,3- Dioxolan-2-yl) acetate (6413-10-1); gamma-decalactone (706-14-9); gamma-undecalactone (104-67-6); geranyl acetate (105-87-3); 3,7-dimethyloct-6-enenitrile (5146-66-7); hexyl salicylate (6259-76-3); isoamyl acetate (123-92-2); isobutyl angelate Isobutylquinoline (93-19-6); Isoeugenol (97-54-1); Isomethyl-α-ionone (127-51-5); Isopropylquinoline (137-79-5); Tricyclodecenyl acetate (5413-60-5); 1-methyl-2-(1,2,2-trimethyl-3-bicyclo[3.1.0]hexanyl)methyl]cyclopropyl] Methanol (198404-98-7); l-Carvone (6485-40-1); (z)-3-Hexen-1-yl methyl carbonate (67633-96-9); 3-(4-tert-butylphenyl)butanal (80-54-6); Limonene (138-86-3, 7705-14-8); Linalool (78-70-6); 3-Methyl-7-propan-2-ylbicyclo[2.2.2] Oct-2-ene-5-carbaldehyde (67845-30-1); 2,6-dimethylhept-5-enal (106-72-9); trans-2-dodecenal (20407-84-5); methyl cinnamate (103-26-4); (4-propan-2-ylcyclohexyl)methanol (5502-75-0); methyl 2-heptyne carbonate (111-12-6); methyl hexyl ketone (111-13-7); methyl octyne carbonate (111-80-8); 6,6-dimethoxy-2,5,5-trimethylhex-2-ene (67674-46-8); methyl salicylate (119-36-8); nerol oxide ( 1786-08-9; octanal (124-13-0); 1-naphthalen-1-ylethanone (941-98-0, 93-08-3); (2r,4s)-2-methyl-4-propyl-1,3-oxathiane (59323-76-1); 2-cyclohexylidene-2-phenylacetonitrile (10461-98-0); 2-methyl-4-methylidene-6-phenyloxane (30310-41-9); 2-cyclohexyl-1,6-heptadiene-3-one (313973-37-4); phenylethyl alcohol (60-12-8); 2-phenoxyethanol (122-99-6); 3-(7,7-dimethyl-4-bicyclo[3.1.1]Hept-3-enyl)propanal (33885-51-7);(e)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (107898-54-4);γ-nonalactone (104-61-0);p-tolylphenyl acetate (101-94-0);(e)-2-ethyl-4-(2,2,3-trimethyl-1-cyclopent-3-enyl)but-2-en-1-ol (28219-61-6);4-(p-hydroxyphenyl)-2-butanone (5471-51-2);4-methyl -2-(2-Methylprop-1-enyl)oxane (16409-43-1); m-(Isocamphyl-5)cyclohexanol (66068-84-6); trans-2,cis-6-nonadienal (557-48-2); trans-2-hexenal (6728-26-3); trans-2-hexenyl 2-methylbutyrate (94089-01-7); trans-anethole (4180-23-8); 2,4-dimethylcyclohex-3-ene-1-carbaldehyde (68039-49-6); Trimofix O (144020-22-4 68610-78-6); undeca-1,3,5-triene (16356-11-9); 4-methyldec-3-en-5-ol (81782-77-6); vanillin (121-33-5); decahydrospiro(furan-2(3h),5'-(4,7)methano(5h)indene) (68480-11-5); and nona-2,6-dienenitrile (67019-89-0).

[0040] Typically, a solid composition may contain from 0.01 to 15% w / w, preferably from 0.01 to 10% w / w, most preferably from 0.01 to 5% w / w of one or more fragrance molecules. The solid composition of the first aspect of the present invention and the solid composition of the second aspect of the present invention, which contain fragrance molecules, remain substantially odorless because the fragrance molecules are complexed with cucurbituril. However, decomplexation of the fragrance molecules, and therefore their release, can be achieved by the action of malodor-causing molecules that complex with cucurbituril and thus replace the fragrance molecules. Thus, the solid composition not only reduces malodor, but also releases fragrance. One advantage of the solid composition is that the molecular exchange between fragrance molecules and malodor molecules can occur even under humid conditions (at least 40% relative humidity at room temperature).

[0041] Decomplexation and release of fragrance molecules can also be achieved by exposure to moisture or liquid water, evaporation, heat and molecular exchange. In one embodiment, the trigger for decomplexation and release of fragrance molecules is increased water activity due to an increase in ambient relative humidity. Water activity can increase to the extent that water molecules bind to the cucurbituril, displacing some of the fragrance molecules and facilitating their release into the air. Contacting the solid composition with water is another way to increase water activity.

[0042] In another embodiment, the trigger for decomplexation and release of fragrance molecules is evaporation or heat. Evaporation and heat are related to each other due to the well-known temperature dependence of vapor pressure. When the interaction between evaporation and heat is considered to be the driving force for fragrance molecule release, the selection of fragrance molecules can be achieved by considering the vapor pressure of each fragrance molecule. For example, for sustained release at room temperature, fragrance molecules with a vapor pressure higher than 0.1 mm Hg at 20°C can be selected, while under heat-induced release conditions, for example, at 100°C or higher, fragrance molecules with a low vapor pressure can provide good results. When considering evaporation and heat as triggers, those skilled in the art will understand the diversity of fragrance molecules in terms of vapor pressure and odor characteristics, which leaves room for creativity.

[0043] In another embodiment, the trigger for decomplexation and release of fragrance molecules is release mediated by molecular exchange of fragrance molecules. Complexes of fragrance molecules with cucurbituril, particularly complexes in which the fragrance molecule contains an oxygen heteroatom, have generally been observed to be weaker than complexes of cucurbituril with nitrogen- or sulfur-containing molecules, or especially complexes of cucurbituril with cationic molecules. Therefore, the compound that triggers decomplexation and release of fragrance molecules can be selected from metal ions and neutral, cationic, zwitterionic, amphoteric, and / or cationic nitrogen-, sulfur-, and / or oxygen-containing substances. Contact between the solid composition and the trigger compound can be achieved by various means. For example, the solid composition and trigger compound of the present invention can be provided as a water-dispersible solid form, such as a powder or granules, which, when dispersed in water, release the trigger, thereby decomplexing and releasing the fragrance molecules. Alternatively, in situ formation of the trigger compound can occur after a pH change.

[0044] Typical trigger compounds include sulfonium derivatives and S-heterocyclic materials, amines and polyamines, and the quaternized forms thereof; imines and polyimines, such as polyethyleneimine and other polyalkyleneimines, and the quaternized forms thereof; aminosilicones, such as aminoalkyl dimethicones; hydroxyamines; cationic surfactants, such as alkylammonium surfactants having one or two alkyl chains with a chain length of from about 16 to about 22 carbon atoms, and from 1 to about 4 carbon atoms, and containing two to three alkyl moieties, optionally containing one or more hydroxyl groups, or a hydroxyalkyl moiety having from about 1 to about 10 ethylene oxide moieties; N-heterocyclic materials, such as oxazoline derivatives, piperazine derivatives, pyridine, bipyridine and polypyridine derivatives, aminopyridinium derivatives, cyclam derivatives, pyrrole derivatives, imidazole derivatives, and the like, and mixtures thereof; fused polycyclic containing materials; and mixtures thereof.

[0045] The solid compositions of the first and second aspects of the present invention can be in the form of an isolation film, a coating attached to an inanimate surface, a porous substrate, or an aggregate. The inanimate surface can be in the form of a porous substrate. Alternatively, the porous substrate itself can be produced by aerating a mixture of thermoplastic and / or one or more thermosetting polymer precursors mixed with one or more cucurbiturils and their derivatives and / or analogs, while in a liquid state, with a suitable gas, such as air, nitrogen, or carbon dioxide, generated either in situ or ex situ, and allowing the mixture to cool while aerated. The isolation film can then be laminated to the inanimate surface. The isolation film can be in the form of, or form part of, a trash can liner. The inanimate surface can be formed of any material suitable for supporting the solid composition, for example, but not limited to, paper, wood, plastic materials, stone, ceramic, metal, textiles, and plaster. More specifically, the inanimate surface or porous substrate can form part of a home or personal care product, such as a feminine hygiene product, a diaper, an incontinence pad, a sanitary napkin, a shoe sole, or an air filter. As used herein, the term "porous" means that a liquid or gas can penetrate, for example, a substrate through pores within the substrate.

[0046] Preferably, when the solid compositions of the first and second aspects of the present invention are in the form of an isolated film, the composition comprises 0.01 to 10% w / w, preferably 0.1 to 7.5% w / w, more preferably 0.5 to 5% w / w, more preferably 0.7 to 3% w / w of one or more cucurbiturils and derivatives and / or analogues thereof.

[0047] Preferably, when the solid composition of the first aspect of the present invention is in the form of a coating, the composition comprises more than 10% w / w, preferably more than 25% w / w, more preferably at least 50% w / w, more preferably at least 75% w / w of one or more cucurbiturils and derivatives and / or analogues thereof, and optionally one or more carbon black and / or inorganic pigments and / or extenders, and preferably no more than 95% w / w, more preferably no more than 98% w / w, and most preferably no more than 99% w / w of one or more cucurbiturils and derivatives and / or analogues thereof, and optionally one or more carbon black and / or inorganic pigments and / or extenders, wherein the solid composition comprises at least an effective amount of cucurbiturils and derivatives and / or analogues thereof. As used herein, the term "effective," in the context of the amount of cucurbituril, means an amount effective to reduce malodour.

[0048] Inorganic pigments and extenders are in particulate form and are well known to those skilled in the art. Examples of inorganic pigments are iron oxide and titanium dioxide, and examples of extenders are talc, diatomaceous earth, calcium carbonate and calcium sulfate.

[0049] When the solid compositions of the first and second aspects of the present invention are in the form of an isolated film, the one or more cucurbiturils and / or derivatives and / or analogues thereof are preferably in the form of particles or particle aggregates with a D90 (using a microscope) equal to or less than the film thickness. Such particles or particle aggregates with a D90 greater than the film thickness have been observed to bridge the two opposing surfaces of the film, thereby structurally weakening the film.

[0050] In a third aspect of the present invention, there is provided a solid composition comprising one or more cucurbiturils and derivatives and / or analogues thereof bound by a thermoplastic and / or thermosetting polymeric medium, wherein when the solid composition is in the form of a coating or aggregate attached to an inanimate surface, the composition comprises more than 10% w / w, preferably more than 25% w / w, more preferably at least 50% w / w, more preferably at least 75% w / w of one or more cucurbiturils and derivatives and / or analogues thereof and optionally one or more of carbon black and / or inorganic pigments and / or extender pigments, and preferably up to 95% w / w, more preferably Solid compositions are provided comprising up to 98% w / w, most preferably up to 99% w / w, of one or more cucurbiturils and derivatives and / or analogues thereof and optionally one or more of carbon black and / or inorganic pigments and / or extender pigments, wherein the solid composition comprises at least an effective amount of one or more cucurbiturils and derivatives and / or analogues thereof.

[0051] In the examples described below, references to mixed (unsubstituted) cucurbiturils refer to any one of Examples 5 to 7 of WO2018 / 115822 (Aqdot Limited). This refers to mixtures containing 1-17 wt. % cucurbit[5]uril, 30-50 wt. % cucurbit[6]uril, 20-37 wt. % cucurbit[7]uril, 10-27 wt. % cucurbit[8]uril, and less than 1 wt. % cucurbit[4]uril, cucurbit[9]uril, and / or higher molecular weight cucurbiturils, based on the total weight of cucurbiturils, prepared according to the methods described in one of the preceding paragraphs. [Example]

[0052] Example 1: Film containing cucurbituril (a) Sample preparation Pellets of ground linear low-density polyethylene (LLDPE) obtained from SABIC (Grade 318B) containing 20% w / w mixed (unsubstituted) cucurbituril ("cucurbituril masterbatch") were prepared by high-speed blending of the cucurbituril and LLDPE powders, followed by passage through a twin-screw extruder at 150°C. The resulting strands were passed through a die and then through rollers, air-cooled, and then chopped into pellets. The pellets were placed in a convection oven at 100°C to minimize moisture absorption.

[0053] An LLDPE film was produced on a 3 m vertical film tower by filling the hopper with an appropriate ratio of "cucurbituril masterbatch" pellets and LLDPE pellets, extruding the mixture at 170°C, forcing the mixture through a circular die, and then blowing the film by introducing air into the mixture. Films containing up to 10% w / w of mixed (unsubstituted) cucurbituril (50% w / w "cucurbituril masterbatch" and 50% w / w LLDPE) were produced with a film thickness of approximately 35 microns.

[0054] (b) (Un)odor Reduction: Headspace Gas Chromatography (GC-HS) A 200 mg film sample was placed inside a 20 mL headspace vial along with odor compounds contained in another 1.5 mL vial, which were provided in the form of either 15 μL (microliters) of a 1.5% w / v aqueous trimethylamine solution or 20 μL (microliters) of a 1% w / v aqueous butyric acid solution.

[0055] Malodor concentrations in the headspace of the headspace vials were determined using headspace gas chromatography (GC-HS). Trimethylamine concentrations were determined using a 60 m CP-Volamine column (Agilent Technologies) with samples equilibrated for 30 minutes in a headspace oven at 50°C. Butyric acid concentrations were determined using a 60 m DB-Wax column (Agilent Technologies) with samples equilibrated for 30 minutes in a headspace oven at 90°C. All measurements were performed in triplicate.

[0056] Concentrations were determined by integrating the chromatographic peak areas detected at the characteristic retention time of each odorous compound. Odor reduction was calculated as a measure of the effectiveness of the film in reducing the odor of each odorous compound, and was calculated as the ratio of the peak area of each odorous compound in the presence of the film containing mixed (unsubstituted) cucurbiturils to the control LLD without mixed (unsubstituted) cucurbiturils. It was defined as the ratio of the peak area of each odor compound recorded in the presence of PE film to that recorded in the presence of PE film.

[0057] The results are summarized in Table 1, which shows that as the concentration of mixed (unsubstituted) cucurbituril increases from 0 to 10% w / w, films containing mixed (unsubstituted) cucurbituril effectively reduce the odors of both trimethylamine and butyric acid.

[0058] [Table 1]

[0059] (c) (bad) odor reduction: sensory performance Two 5 x 5 cm trimethylamine-impregnated polycotton (cotton and polyester laminate) swatches were prepared by adding 22.2 μL (microliters) of 45% w / v trimethylamine in water to each swatch. One swatch was placed in a 20 cm long LLDPE (control) film tube, and the other was placed in a 20 cm long LLDPE film tube containing either 2% w / w or 10% w / w mixed (unsubstituted) cucurbiturils.

[0060] The ends of all film tubes were sealed with cable ties, and each sealed tube was placed into an individual 10 L Nalophan sample bag, which was then sealed, inflated with compressed air, and equilibrated for 1 hour at 20°C and 40-60% relative humidity. The headspace of the Nalophan bag was then smelled for (mal)odor intensity and hedonic tone by a six-person trained panel in a blinded paired comparison study.

[0061] Odor intensity, measured together with odor concentration, is the perceived strength of an odor above its detection threshold. Odors are described on a seven-point scale ranging from imperceptible to very strong (6 very strong; 5 very strong; 4 strong; 3 distinct; 2 weak; 1 very weak; 0 undetectable). Odors may have different perceived intensities at the same concentration.

[0062] Hedonic tone measures the pleasantness of an odor, which can vary from pleasant to unpleasant with increasing concentration, intensity, and frequency. The analysis determined the concentration at which an odor becomes unpleasant and rated the odor on a 9-point pleasant / unpleasant scale (+4 extremely pleasant; +3 very pleasant; +2 pleasant; +1 slightly pleasant; 0 neutral; -1 slightly unpleasant; -2 unpleasant; -3 very unpleasant; -4 extremely unpleasant).

[0063] A trained panel of six people was trained monthly to use a set of sniff sticks containing various levels of butanol and to assess odor intensity broadly according to European standard EN 13725: Air quality - Determination of odor concentration by dynamic olfactometry. Each comparison experiment was performed in triplicate.

[0064] The results are summarized in Tables 2 and 3, which show that in the LLDPE film containing 2% w / w of the mixed (unsubstituted) cucurbituril, the difference between the two films was marginally significant in replication 1 (0.01 < P < 0.05), highly significant in replication 2 (P < 0.005), and significant in replication 3 (0.005 < P < 0.01). P is the probability that the results occur randomly, as calculated by a two-sided t-test. In the LLDPE film containing 10% w / w of the mixed (unsubstituted) cucurbituril, the difference between the two films was highly significant in all three replications (P < 0.005).

[0065] [Table 2]

[0066] [Table 3]

[0067] Example 2: Coating of mixed (unsubstituted) cucurbituril and polyvinyl alcohol on a planar or porous support Cucurbituril has been shown to be an effective substance for eliminating malodors and can be used in a liquid form (suspension) that allows for delivery as an aerosol. Cucurbituril can be effective in solid form, but as a simple powder, it can have drawbacks associated with dusting, inhalation, or unwanted deposition. The aforementioned drawbacks are solved by immobilizing cucurbituril on a substrate. Immobilization can be achieved by combining cucurbituril with a binder and applying the resulting mixture as a coating to the substrate. Other substances can be included in the coating to provide reinforcement of the coating layer or to assist in the application of the coating.

[0068] (a) Sample preparation An aqueous suspension containing mixed (unsubstituted) cucurbituril and polyvinyl alcohol was prepared by combining equal masses of a 50% w / w aqueous slurry of mixed (unsubstituted) cucurbituril and a 2.5% w / w aqueous solution of polyvinyl alcohol. The resulting composition contained 1.25% w / w polyvinyl alcohol and 25% w / w mixed (unsubstituted) cucurbituril in water.

[0069] A 50% w / w aqueous slurry of mixed (unsubstituted) cucurbituril was prepared by adding water to powdered mixed (unsubstituted) cucurbituril and stirring the resulting mixture with a glass rod. A polyvinyl alcohol solution in water was prepared by adding polyvinyl alcohol granules to water with stirring, then heating the mixture to 90°C until dissolution was complete. Two polyvinyl alcohol samples were used, both supplied by Sigma-Aldrich, with a degree of hydrolysis of 88% and nominal molecular weights of 67 kDa (Mowiol 8-88) and 205 kDa (Mowiol 40-88), correspondingly designated low MW and high MW, respectively. The 1s of a 2.5% w / w polyvinyl alcohol solution were analyzed. -1 and viscosities at 20°C were 3.2 and 9.8 mPa.s for the low MW and high MW samples, respectively. It was.

[0070] A 1 cm x 5 cm cardboard swatch was manually coated by dipping with an aqueous suspension of mixed (unsubstituted) cucurbituril and polyvinyl alcohol, then dried overnight in an oven at 45° C. A 1 cm x 1 cm x 2 cm piece of artificial sponge was filled by immersion in the aqueous suspension of mixed (unsubstituted) cucurbituril and polyvinyl alcohol, the excess was squeezed out, and then dried overnight in an oven at 45° C. The amount of the aqueous suspension of mixed (unsubstituted) cucurbituril and polyvinyl alcohol, and therefore the amount of mixed (unsubstituted) cucurbituril on each substrate sample, was determined by mass.

[0071] (b) (bad) odor reduction: gas chromatography headspace analysis 4 μL (microliter) of n-butyric acid (a model malodor compound) was added to a 20 mL headspace vial with each support. Malodor concentrations were measured by gas chromatography headspace analysis (GC-HS). Analysis used a 60 m DB-wax column (Agilent Technologies) with the sample equilibrated in a headspace oven at 90 °C for 30 minutes. 10 mL of headspace was extracted for analysis. All measurements were performed in triplicate.

[0072] Malodor concentrations were determined by integrating the peak areas detected at the characteristic retention time of n-butyric acid. Malodor reduction was calculated as the ratio of the malodor peak in the presence of the mixed (unsubstituted) cucurbituril-containing substrate to the malodor peak recorded in the presence of the control sample (substrate without mixed (unsubstituted) cucurbituril).

[0073] i) Cardboard substrate The results are presented in Table 4, expressed in terms of the percent reduction (R) in n-butyric acid concentration compared to a paper substrate in the absence of a coating of mixed (unsubstituted) cucurbituril and polyvinyl alcohol. The effect of mixed (unsubstituted) cucurbituril on malodor reduction was determined both with and without polyvinyl alcohol. To compare the various coatings, the malodor reduction R was divided by the amount of mixed (unsubstituted) cucurbituril on each substrate sample.

[0074] [Table 4]

[0075] The presence of mixed (unsubstituted) cucurbituril, either in coated form with polyvinyl alcohol or as a powder, significantly reduces the headspace malodor concentration. The reduction efficiency of is obtained to provide further comparison.

[0076] ii) Sponge substrate The results are presented in Table 5, expressed in terms of the percent reduction (R) in n-butyric acid concentration compared to the sponge substrate in the absence of the mixed (unsubstituted) cucurbituril and polyvinyl alcohol coating. The effect of the mixed (unsubstituted) cucurbituril on malodor reduction was determined both with and without polyvinyl alcohol. To compare the various samples, the malodor reduction R was divided by the amount of mixed (unsubstituted) cucurbituril on each sample.

[0077] [Table 5]

[0078] The presence of mixed (unsubstituted) cucurbituril either in coated form (with polyvinyl alcohol) or as a suspension in water (without polyvinyl alcohol) reduces headspace malodor concentrations by approximately 86%. The malodor reduction efficiency per gram of mixed (unsubstituted) cucurbituril is similar in the presence and absence of polyvinyl alcohol.

[0079] iii) No substrate Malodor reduction experiments were conducted in the absence of substrate, using levels of mixed (unsubstituted) cucurbituril up to 1 g, and the malodor reduction results are summarized in Table 6. The data in Table 6 are compared graphically with the data in Tables 4 and 5 in Figure 1, which shows R (%) versus mass of mixed (unsubstituted) cucurbituril (g), and in Figure 2, which shows R / mass of mixed (unsubstituted) cucurbituril (% / g) versus mixed (unsubstituted) cucurbituril (g).

[0080] Referring to Figure 1, mixed (unsubstituted) cucurbituril and polyvinyl alcohol without a substrate (filled symbols) are significantly less efficient at reducing malodors than free mixed (unsubstituted) cucurbituril or mixed (unsubstituted) cucurbituril and polyvinyl alcohol coated onto a cardboard or sponge substrate. When mixed (unsubstituted) cucurbituril and polyvinyl alcohol are coated onto a substrate, the polyvinyl alcohol appears to be ineffective at reducing malodors.

[0081] Referring to Figure 2, the malodor reduction of mixed (unsubstituted) cucurbituril immobilized on cardboard or sponge substrates is indistinguishable from that of free mixed (unsubstituted) cucurbituril (no substrate).

[0082] [Table 6]

[0083] Example 2 demonstrates that mixed (unsubstituted) cucurbiturils can be restrained to cardboard or sponge substrates without compromising malodor performance efficiency. Example 3: Cucurbituril Aggregates (a) Sample preparation Mixed (unsubstituted) cucurbituril aggregates were subjected to a 200-well flow rate (200-250 s) of 100-130°C inlet air at an inlet temperature of 100-130°C and an inlet air flow of 60-130 m / s. 3 The powders were produced in a Glatt-type fluidized bed spray granulator experimental unit with a 1000-µL / h capacity. Polyvinylpyrrolidone (PVP Luvitex K30) and polyvinyl alcohol (PVOH Poval 4-88) were used as binders. Mixed (unsubstituted) cucurbituril powder was introduced into a preheated chamber, and water or an aqueous binder solution was sprayed onto the powder to form mixed (unsubstituted) cucurbituril aggregates with diameters ranging from 1.0 to 3.15 mm. Details of the cucurbituril aggregates are summarized in Table 7.

[0084] [Table 7]

[0085] Glass beads coated with mixed (unsubstituted) cucurbiturils were placed in a 100-130°C inlet airflow chamber at an inlet temperature of 100-130°C and an inlet airflow of 80-120 m / s. 3 The coating was produced in a Glatt-type fluidized bed spray granulator laboratory unit with a flow rate of 1 / h. Glass beads (Poraver, diameter 0.5-1 mm or 1.0-2.0 mm) were introduced into a preheated chamber in a 1:1 mass ratio with the mixed (unsubstituted) cucurbituril, and an aqueous suspension of the mixed (unsubstituted) cucurbituril and binder (45% w / w solids) was sprayed onto the beads. Details of the cucurbituril-coated glass beads are summarized in Table 8.

[0086] [Table 8]

[0087] (b) (Un)odor Reduction: Gas Chromatography Headspace Analysis (GC-HS) The ability of mixed (unsubstituted) cucurbituril aggregates and mixed (unsubstituted) cucurbituril-coated beads to absorb undesirable target compounds was assessed by GC-HS. It has been decided.

[0088] The model malodor compounds were n-butyric acid, benzene, or ethylbenzene. 4 μL (microliters) of each malodor compound was placed in a 1.5 mL vial inside a 20 mL headspace vial containing mixed (unsubstituted) cucurbituril aggregates or beads coated with mixed (unsubstituted) cucurbituril. Malodor compound concentrations were measured by gas chromatography-headspace analysis (GC-HS). Analysis was performed using a 60 m DB-wax column (Agilent Technologies) with the sample equilibrated for 30 min in a headspace oven at 90 °C (n-butyric acid only) or 32 °C (n-butyric acid, benzene, and ethylbenzene). 10 mL of headspace gas was extracted for analysis. All measurements were performed in triplicate. The results are summarized in Tables 9–11.

[0089] The malodorous compound concentrations were determined by integrating the peak areas detected at the characteristic retention times of the malodorous compounds. Reduction was calculated as the ratio of the malodorous compound peak in the presence of mixed (unsubstituted) cucurbituril aggregates or beads coated with mixed (unsubstituted) cucurbituril to the control peak (no cucurbituril). Samples were compared using a constant amount of mixed (unsubstituted) cucurbituril at a 1:10 mass ratio of (malodorous) compounds to mixed (unsubstituted) cucurbituril.

[0090] [Table 9]

[0091] [Table 10]

[0092] [Table 11]

[0093] Mixed (unsubstituted) cucurbituril aggregates and glass beads coated with mixed (unsubstituted) cucurbituril absorb malodorous compounds. Absorption occurs over a range of temperatures.

Claims

1. A method for reducing malodor, comprising the step of providing a solid composition comprising one or more cucurbiturils and derivatives and / or analogs thereof suspended in and / or bound by a thermoplastic and / or thermosetting polymer medium, wherein the source of the malodor is external.

2. 2. The method of claim 1, wherein the cucurbituril is selected from the group consisting of cucurbit[5]uril, cucurbit[6]uril, cucurbit[7]uril, cucurbit[8]uril, and mixtures thereof.

3. 3. The method of claim 2, wherein the concentration of cucurbit[5]uril is from about 0 to about 99 wt. %, more particularly from about 0.1 to about 75 wt. %, more particularly from about 0.5 to about 50 wt. %, more particularly from about 1 to about 30 wt. %, more particularly from about 1 to about 25 wt. %, more particularly from about 1 to about 20 wt. %, based on the total weight of cucurbituril in the composition.

4. 4. The method of claim 2 or 3, wherein the concentration of cucurbit[6]uril is from about 0.1 to about 99 wt.%, more particularly from about 1 to about 75 wt.%, more particularly from about 5 to about 60 wt.%, more particularly from about 20 to about 55 wt.%, more particularly from about 35 to about 55 wt.%, based on the total weight of cucurbituril in the composition.

5. 5. The method of claim 2, wherein the concentration of cucurbit[7]uril is from about 0.1 to about 99% by weight, more particularly from about 5 to about 75% by weight, more particularly from about 10 to about 60% by weight, more particularly from about 20 to about 45% by weight, based on the total weight of cucurbituril in the composition.

6. 6. The method of claim 2, wherein the concentration of cucurbit[7]uril is less than 45% by weight, based on the total weight of cucurbituril in the composition.

7. 7. The method of any one of claims 2 to 6, wherein the concentration of cucurbit[8]uril is from about 0.1 to 99 wt.%, more particularly from about 0.5 to about 75 wt.%, more particularly from about 1 to about 30 wt.%, more particularly from about 5 to about 25 wt.%, more particularly from about 10 to about 20 wt.%, based on the total weight of cucurbituril in the composition.

8. 8. The method of any one of claims 2 to 7, wherein the total concentration of cucurbit[5]uril, cucurbit[6]uril, cucurbit[7]uril and cucurbit[8]uril in the composition is greater than 75% by weight, in particular greater than about 90% by weight, in particular greater than about 99% by weight, based on the total weight of cucurbiturils in the composition.

9. 9. The method of any one of claims 2 to 8, wherein the composition comprises 1 to 17 wt% cucurbit[5]uril, 30 to 50 wt% cucurbit[6]uril, 20 to 37 wt% cucurbit[7]uril, 10 to 27 wt% cucurbit[8]uril, and less than 1 wt% cucurbit[4]uril, cucurbit[9]uril, and / or higher molecular weight cucurbiturils, based on the total weight of cucurbiturils in the composition.

10. The thermoplastic medium may be selected from linear low density polyethylene, low density polyethylene, medium density polyethylene, high density polyethylene, polyethylene, polypropylene, polyester, polyethylene terephthalate, polyacrylate homo- and copolymers, polymethacrylate homo- and copolymers, poly(methyl methacrylate), poly(acrylonitrile butadiene styrene), polyamide, poly(lactic acid), poly(benzimidazole), polycarbonate, poly(ether sulfone), poly(oxymethylene), poly(ether ether ketone), poly 10. The method of any one of the preceding claims, wherein the polymer is selected from the group consisting of (etherimide), polystyrene, polyvinyl chloride, polyvinylidene fluoride, polytetrafluoroethylene, cellulose, polysaccharides, polyvinyl alcohol, polyvinyl acetate, partially hydrolyzed polyvinyl acetate, polyvinylpyrrolidone, and mixtures thereof.

11. 10. The method of any one of the preceding claims, wherein the thermosetting medium is selected from the group consisting of polyurethanes, polyurea-polyurethane hybrids, vulcanized rubbers, polyacrylates, polymethacrylates, phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins, epoxy resins, benzoxazines and hybrids of epoxy and phenolic resins with benzoxazines, polyimides, polybismaleimides, cyanate ester resins, furan resins, silicone resins, vinyl ester resins, alkyd resins, and mixtures thereof.

12. 10. The method of any one of the preceding claims, wherein the composition further comprises one or more fragrance molecules.

13. 10. The method of any one of the preceding claims, wherein the solid composition is in the form of an isolated film, a coating attached to an inanimate surface, a porous substrate, or an aggregate.

14. 14. The method of claim 13, wherein when the solid composition is in the form of an isolated film, the composition comprises 0.01 to 10% w / w, preferably 0.1 to 7.5% w / w, more preferably 0.5 to 5% w / w, more preferably 0.7 to 3% w / w of one or more cucurbiturils and derivatives and / or analogues thereof.

15. 15. The method of claim 13 or 14, wherein when the solid composition is in the form of an isolated film, the one or more cucurbiturils and derivatives and / or analogs thereof are in the form of particles or aggregates of particles with a D90 of less than or equal to the thickness of the film.

16. 14. The method of claim 13, wherein when the solid composition is in the form of a coating, the composition comprises more than 10% w / w, preferably more than 25% w / w, more preferably at least 50% w / w, more preferably at least 75% w / w of one or more cucurbiturils and derivatives and / or analogues thereof and optionally one or more carbon black and / or pigments and / or extenders, and preferably no more than 95% w / w, more preferably no more than 98% w / w, most preferably no more than 99% w / w of one or more cucurbiturils and derivatives and / or analogues thereof and optionally one or more carbon black and / or pigments and / or extenders, and the solid composition comprises at least an effective amount of cucurbiturils and derivatives and / or analogues thereof.

17. A solid composition comprising one or more cucurbiturils and derivatives and / or analogues thereof suspended in a thermoplastic and / or thermosetting polymer medium, and further comprising one or more fragrance molecules.

18. 18. The solid composition of claim 17, in the form of an isolated film, a coating attached to an inanimate surface, or a porous substrate.

19. 19. A solid composition according to claim 17 or 18, wherein when the solid composition is in the form of an isolated film, the one or more cucurbiturils and derivatives and / or analogues thereof are in the form of particles with a D90 of less than or equal to the thickness of the film.

20. One or more cucurbits bound by a thermoplastic and / or thermosetting polymer medium A solid composition comprising cucurbituril and derivatives and / or analogues thereof, wherein when the solid composition is in the form of a coating or aggregate attached to an inanimate surface, the composition comprises more than 10% w / w, preferably more than 25% w / w, more preferably at least 50% w / w, more preferably at least 75% w / w of one or more cucurbiturils and derivatives and / or analogues thereof and optionally one or more carbon black and / or inorganic pigments and / or extender pigments, and preferably no more than 95% w / w, more preferably no more than 98% w / w, most preferably no more than 99% w / w of one or more cucurbiturils and derivatives and / or analogues thereof and optionally one or more carbon black and / or inorganic pigments and / or extender pigments, wherein the solid composition comprises at least an effective amount of one or more cucurbiturils and derivatives and / or analogues thereof.

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