WO2024102302A1 - Multifunctional boosters for antimicrobial preservatives and applications thereof - Google Patents

Multifunctional boosters for antimicrobial preservatives and applications thereof Download PDF

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Publication number
WO2024102302A1
WO2024102302A1 PCT/US2023/036733 US2023036733W WO2024102302A1 WO 2024102302 A1 WO2024102302 A1 WO 2024102302A1 US 2023036733 W US2023036733 W US 2023036733W WO 2024102302 A1 WO2024102302 A1 WO 2024102302A1
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alkenyl
composition
alkyl
acid
antimicrobial
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PCT/US2023/036733
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French (fr)
Inventor
Selvanathan Arumugam
Ziang LI
Randall Wayne STEPHENS
Weiyu YIN
Soonjoo Son
Anna BREZDEN
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Lanxess Corporation
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Publication of WO2024102302A1 publication Critical patent/WO2024102302A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Definitions

  • the present invention relates generally to multifunctional boosters to enhance the antimicrobial activity of antimicrobial preservatives and applications thereof in personal care products, cosmetic products and home care products, and, more particularly, to certain ether compounds as such multifunctional boosters.
  • BACKGROUND OF THE INVENTION Protection against microbial contamination of personal care products, cosmetic products, and home care products is of high importance to these product industries.
  • Traditional preservatives, such as isothiazolinones, formaldehyde releasers, parabens, and IPBC, are under increased scrutiny from regulatory agencies and environmental working groups.
  • product formulators are seeking solutions to reduce the dosing levels of traditional preservatives without compromising the level of preservation.
  • Many product formulators are also turning to “soft” preservatives, such as phenoxyethanol, alcohols and/or organic acids. Because soft preservatives alone often do not provide robust full-spectrum antimicrobial efficacy, particularly at desired dosing levels, formulators may use them in combination with booster compounds to provide more robust protection to product compositions.
  • product compositions include ingredients which do not directly benefit the target substrate but are necessary to provide rheological or other chemical and/or mechanical properties to the applied product.
  • WO 2014/191258 A2 is directed to antimicrobial compositions comprising certain glyceryl ethers
  • WO 2022/128882 A1 is directed to a combination of n-heptyl-glyceryl ether and certain preservative compounds.
  • the present disclosure is further based on the discovered multifunctional nature of the presently disclosed ether compounds, as it was surprisingly found that such compounds exhibit one or more further properties, such as one or more of antioxidant, surfactant, humectant and/or chelating properties, which can be provided to product formulations.
  • a personal care, cosmetic or home care product composition comprising an antimicrobial preservative and an ether compound of formula (I) (I), C 6 alkenyl, –R 6 –OH, or –R 8 –O–R 9 ;
  • R 2 is –C 1 -C 6 alkyl, –C 2 -C 6 alkenyl, –R 6 –OH, –O–R 7 , or –R 8 –O–R 9 ;
  • R 3 is –OH, –R 6 –OH, –O–R 7 or –R 8 –O–R 9 ;
  • R 4 is –C 2 -C 5 alkenyl; and
  • R 5 is H, –C 1 -C 5 alkyl, or –C 2 -C 5 alkenyl; and, with respect to R 1 , R 2 and R 3 independently of one another, R 6 is –C 1 -C 6 alkylene or –C 3 -C 6 alkenyl
  • a method of providing antimicrobial activity to a personal care, cosmetic or home care product composition comprises adding to the composition an antimicrobial preservative and an ether compound of formula (I) as described herein.
  • the present disclosure provides for the use of an ether compound of formula (I) as described herein for enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition.
  • a method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) as described herein.
  • the antimicrobial efficacy is enhanced as compared to an equal amount of the antimicrobial preservative without the ether compound.
  • an antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) as described herein.
  • the ether compounds of the present disclosure are of the formula (I): , alkenyl, –R 6 –OH, or –R 8 –O–R 9 ;
  • R 2 is –C 1 -C 6 alkyl, –C 2 -C 6 alkenyl, –R 6 –OH, –O–R 7 , or –R 8 –O–R 9 ;
  • R3 is –OH, –R6–OH, –O–R7 or –R8–O–R9;
  • R 4 is –C 2 -C 5 alkenyl (e.g., C 2 -C 3 alkenyl); and
  • R 5 is H, –C 1 -C 5 alkyl (e.g., C 1 -C 3 alkyl), or –C 2 -C 5 alkenyl (e.g., C 2 -C 3 alkenyl).
  • R 6 is – C 1 -C 6 alkylene (e.g., –C 1 -C 4 alkylene or –C 1 -C 2 alkylene) or –C 3 -C 6 alkenylene (e.g., –C 3 -C 4 alkenylene)
  • R 7 is –C 1 -C 6 alkyl (e.g., –C 1 -C 4 alkyl or –C 1 -C 2 alkyl) or –C 3 -C 6 alkenyl (e.g., –C 3 -C 4 alkenyl)
  • R 8 is –C 1 -C 5 alkylene (e.g., –C 1 -C 3 alkylene) or –C 3 -C 5 alkenylene (e.g., –C 3 alkenylene)
  • R 9 is –C 1 -C 5 alkyl (e.g.
  • At least one of R 1 , R 2 , or R 3 contains a –OH group.
  • at least one of R 1 , R 2 , or R 3 may contain a –OH group, and at least one other of R 1 , R 2 , or R 3 may contain an ether group.
  • at least two of R 1 , R 2 , or R 3 contain a –OH group.
  • the other of R 1 , R 2 , or R 3 may, but need not, contain a –OH group or an ether group.
  • R 1 , R 2 , and R 3 each contains a –OH group.
  • R 1 , R 2 , or R 3 contains a –OH group, and the remaining two each contains an ether group.
  • references to R 1 , R 2 , and/or R 3 containing “a –OH group” or “an ether group,” as applicable, refer to the respective groups described herein from which R 1 , R 2 , and R 3 are selected that contain the specified functional group (i.e., that contain hydroxyl or ether). For example, where R 3 is said to contain a –OH group, this indicates R 3 is –OH or –R 6 –OH.
  • R 3 is said to contain an ether group
  • R 3 is –O–R 7 or –R 8 –O–R 9 .
  • R 1 , R 2 , and/or R 3 are said to have an oxygen-containing group or functionality.
  • the total number of carbons in R 1 , R 2 , and R 3 combined is typically no more than 12, such as no more than 8 or no more than 6.
  • the total number of carbons in R 1 , R 2 , and R 3 combined ranges from 1 to 12, such as from 2 to 12, from 3 to 12 or from 4 to 12, often from 1 to 8, from 2 to 8, from 3 to 8, from 4 to 8, from 1 to 6, from 2 to 6, or from 3 to 6.
  • the total number of carbons in R 8 and R 9 combined is typically no more than 6, or, in many embodiments, no more than 4. More than one ether compound of formula (I) may be present or used in the compositions and methods of the present disclosure.
  • R 1 in formula (I) is H, –C 1 -C 4 alkyl, –C 2 -C 4 alkenyl, –R 6 –OH, or –R 8 –O–R 9 , where R 6 , R 8 , and R 9 are as described herein.
  • R 1 is H, –C 1 -C 4 alkyl, –C 2 -C 4 alkenyl or –R 6 –OH, often H, –R 6 –OH or –C 1 -C 4 alkyl (e.g., methyl or ethyl).
  • R 1 is –R 6 –OH or –R 8 –O–R 9 , preferably –R 6 –OH, where R 6 , R 8 , and R 9 are as described herein.
  • R 2 in formula (I) is –C 1 -C 4 alkyl, –C 2 -C 4 alkenyl, –R 6 –OH, –O–R 7 , or –R 8 –O–R 9 , where R 6 -R 9 are as described herein.
  • R 2 is –C 1 -C 4 alkyl (e.g., –C 1 -C 2 alkyl) or –C 2 -C 4 alkenyl.
  • R 2 is R 6 –OH, –O–R 7 , or –R 8 –O–R 9 , preferably R 6 –OH, where R 6 -R 9 are as described herein.
  • R 3 in formula (I) is –OH, –R 6 –OH, –O–R 7 or –R 8 –O–R 9 , where R 6 -R 9 are as described herein.
  • R 2 and R 3 are each independently selected to have an oxygen-containing functionality as described herein.
  • R 2 is –R 6 –OH, –O–R 7 , or –R 8 –O–R 9
  • R 3 is —OH, –R 6 –OH, –O–R 7 or – R 8 –O–R 9 , where R 6 -R 9 are as described herein.
  • R 2 and R 3 may, but need not, be the same.
  • R 2 is –R 6 –OH and R 3 is –OH or –R 6 –OH.
  • at least one of R 2 or R 3 contains a –OH group and the other contains an ether group.
  • R 2 may be –R 6 –OH and R 3 may be –O–R 7 or –R 8 –O–R 9 .
  • R 2 and R 3 are each independently –O–R 7 or –R 8 –O–R 9 , preferably where R 1 is –R 6 –OH.
  • R 2 and R 3 are each –R 6 –OH, are each –O–R 7 , or are each–R 8 –O–R 9 , the R 6 -R 9 groups as applicable may, but need not, be the same in each of R 2 and R 3 (the same applies with respect to the R 6 , R 8 and R 9 groups of R 1 in relation to R 2 and R 3 ).
  • R 2 and R 3 are each independently –R 6 –OH, where R 6 for R 2 may be different or the same as R 6 for R 3 , such as where R 6 in each is the same or different –C 1 -C 6 alkylene or –C 1 -C 4 alkylene (e.g., chosen from methylene and ethylene).
  • R 2 and R 3 are each independently –R 8 –O–R 9 , where R 8 and R 9 for R 2 may be different or the same as for R 3 (e.g., where R 8 in each is the same or different –C 1 -C 5 alkylene or –C 1 -C 3 alkylene (e.g., chosen from methylene and ethylene) and R 9 in each is the same or different –C 3 -C 5 alkenyl (e.g., –C 3 alkenyl).
  • R 2 is –O–R 7 or –R 8 –O–R 9 , preferably –R 8 –O–R 9
  • R3 is —OH or –R6–OH, such as where R2 is –R8–O–R9, and R3 is –R6–OH (and, for example, where R 6 and R 8 are each independently alkylene as described herein, and R 9 is alkenyl as described herein).
  • R 2 is alkyl or alkenyl as described herein
  • R 3 is– OH, –R 6 –OH, –O–R 7 , or –R 8 –O–R 9 .
  • R 1 is preferably –R 6 –OH in embodiments where neither R 2 nor R 3 contains a –OH group.
  • R 1 is preferably –R 6 –OH in embodiments where neither R 2 nor R 3 contains a –OH group.
  • the selections for R 1 as described herein may be chosen with any combination of R 2 and R 3 as described herein, preferably wherein at least one of R 1 , R 2 , or R 3 contains a –OH group.
  • the same applies to the selections for R 2 relative to R 1 and R 3 and to the selections for R 3 relative to R 1 and R 2 preferably, in each case, wherein at least one of R 1 , R 2 , or R 3 contains a –OH group.
  • any combination of R 2 and R 3 is selected, preferably wherein at least one of R 2 or R 3 contains a —OH group (e.g., R 2 is alkyl, alkenyl or –R 6 –OH as described herein and R 3 is —OH or –R 6 –OH), and R 1 is H, –R 6 –OH, alkyl or alkenyl as described herein, often H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl).
  • R 2 is alkyl, alkenyl or –R 6 –OH as described herein and R 3 is –OH or –R 6 –OH
  • R 1 is H, –R 6 –OH, alkyl or alkenyl as described herein, often H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl
  • any combination of R 2 and R 3 is selected where R 2 and R 3 each independently has an oxygen-containing functionality, preferably wherein at least one (or both) of R 2 or R 3 contains a –OH group, and R 1 is H, –R 6 –OH, alkyl or alkenyl as described herein, often H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl).
  • R 1 , R 2 and R 3 in formula (I) each may be independently selected to have an oxygen-containing functionality as described herein, preferably wherein at least one of R 1 , R 2 , or R 3 contains a –OH group.
  • R 1 is –R 6 –OH or –R 8 –O–R 9
  • R 2 is –R 6 –OH, –O–R 7 , or –R 8 –O–R 9
  • R 3 is —OH, – R 6 –OH, –O–R 7 or –R 8 –O–R 9
  • R 6 -R 9 are as described herein, preferably wherein at least one of R1, R2, or R3 contains a –OH group.
  • R1 and R2 may each independently be –R6–OH
  • R 3 may be –OH or –R 6 –OH.
  • R 6 in R 1 , R 2 and R 3 may be the same or different, such as where R 6 is the same or different –C 1 -C 6 alkylene or –C 1 -C 4 alkylene (e.g., chosen from methylene and ethylene).
  • R 4 in formula (I) contains a non-aromatic carbon–carbon double bond. More specifically, R 4 is –C 2 - C 5 alkenyl.
  • R 4 is C 2 -C 3 alkenyl, preferably C 2 alkenyl.
  • R 5 in formula (I) is H, –C 1 -C 5 alkyl (e.g., C 1 -C 3 alkyl), or –C 2 -C 5 alkenyl (e.g., C 2 -C 3 alkenyl).
  • R 1 to R 4 as described herein is selected, and R 5 is H, particularly, for example, where R 4 is C 2 alkenyl, meaning R 4 , R 5 and the carbon atom to which they are each attached collectively form an allyl group.
  • the ether compounds of formula (I) are said to be allyl ether compounds.
  • R 5 is a short chain alkyl or alkenyl as described herein.
  • Alkyl, alkylene, alkenyl, and “alkenylene” groups as used herein may be unbranched or branched depending upon the selected chain length.
  • ether compounds of the formula (I) include, without limitation, 2-(allyloxymethyl)-2- ethyl-1,3-propanediol (i.e., trimethylolpropane allyl ether), 2,2-bis(allyloxymethyl)-2- ethylpropanediol (i.e., trimethylolpropane diallyl ether), 3-allyloxy-1,2-propanediol and 2,2- bis(hydroxymethyl)-1,3-propanediol allyl ether (i.e., pentaerythritol allyl ether).
  • the ether compound of formula (I) may be synthesized according to known methods or may be obtained as a commercially available compound.
  • the ether compounds as described herein have one or more properties chosen from antioxidant, surfactant, humectant and chelating properties, such as described or demonstrated herein.
  • at least two of R 1 , R 2 , or R 3 contain a –OH group, and the ether compound has at least a chelating property.
  • at least two of R 1 , R 2 , or R 3 contain a –OH group, and the ether compound has at least an antioxidant property.
  • At least two of R 1 , R 2 , or R 3 contain a –OH group, and the ether compound has at least an antioxidant property and a chelating property, or at least an antioxidant property, a chelating property and a surfactant property, or at least an antioxidant property, a chelating property, a surfactant property and a humectant property.
  • R 2 may be –R 6 –OH
  • R 3 may be –OH or – R 6 –OH
  • R 1 may be as described herein, preferably where R 1 is H, –R 6 –OH, alkyl or alkenyl as described herein, often H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl).
  • the ether compound of formula (I) shows a ⁇ M Trolox equivalents (TE) value (i.e., ⁇ mol Trolox/L sample) of at least 25 ⁇ M TE, more preferably at least 50 ⁇ M TE or at least 75 ⁇ M TE, in particular at least 100 ⁇ M TE, at least 125 ⁇ M TE or at least 150 ⁇ M TE, where the TE value is determined according to the assay procedure of the Activated ABTS Antioxidant Assay Kit (Cat# AOX-14) (instruction manual ZBM0123.00, April 2021).
  • TE Trolox equivalents
  • the ether compound of formula (I) shows a ⁇ M EDTA equivalents value (i.e., ⁇ mol EDTA/L sample) of at least 50 ⁇ M EDTA equivalents, more preferably 6 Docket No.: P243 00001 ⁇ WO ⁇ PCT at least 75 ⁇ M EDTA equivalents or at least 100 ⁇ M EDTA equivalents, in particular at least 150 ⁇ M EDTA equivalents, at least 175 ⁇ M EDTA equivalents or at least 200 ⁇ M EDTA equivalents, where the EDTA equivalents value is determined according to the assay procedure of the Cupric Ion Chelating Assay Kit (Cat# AOX-16) (instruction manual ZBM0125.00, July 2021).
  • a ⁇ M EDTA equivalents value i.e., ⁇ mol EDTA/L sample
  • antimicrobial preservative traditional and/or soft preservatives may be used.
  • the ether compounds of formula (I) can be used to decrease the number and/or amount of such antimicrobial preservatives otherwise required to achieve desired preservation activity in personal care products, cosmetics products and home care products. Suitable antimicrobial preservatives for personal care products, cosmetic products, and home care products are known in the art.
  • Examples of such traditional preservatives include isothiazolinones (e.g., 5-chloro-2-methyl-4-isothiazolin-3-one (CMIT), 2-methyl-4-isothiazolin-3-one (MIT), and 1,2-benzisothiazolin-3-one (BIT)), formaldehyde releasers (e.g., bronopol and 1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione), and parabens (e.g., methylparaben, ethylparaben, propylparaben, and butylparaben).
  • the antimicrobial preservative may be a soft preservative.
  • the antimicrobial preservative comprises an isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), an alkylhydroxamic acid and/or salt thereof (e.g., hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid, salts thereof, combinations thereof, preferably caprylhydroxamic acid and/or a salt thereof), an aromatic aldehyde (e.g., cinnamic aldehyde), an alcohol (e.g., an aromatic alcohol, such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic alcohol, a phenolic compound, such as hydroxyacetophenone, combinations thereof), a diol (e.g., bronopol, glycols, such as 1,2-propanediol, 1,3-butanediol
  • the antimicrobial preservative may comprise an alkylhydroxamic acid and/or salt thereof (preferably, hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid and/or salt thereof or combination thereof, particularly caprylhydroxamic acid and/or salt thereof), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, 1,2- pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., caprylyl glycol), bronopol, 7 Docket No.: P243 00001 ⁇ WO ⁇ PCT ethylhexy
  • the antimicrobial preservative comprises an isothiazolinone, an aromatic aldehyde, an aromatic alcohol, an aromatic ether, an organic acid, a salt or ester of an organic acid, a pyrithione, ethyl lauroyl arginate (LAE) or a combination thereof.
  • the antimicrobial preservative may comprise caprylhydroxamic acid, phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenethyl alcohol, ethyl lauroyl arginate (LAE), CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4- dienoic acid, 4-hydroxybenzoic acid, an ester or salt of said organic acids (e.g., sodium benzoate, potassium sorbate and the like), or a combination thereof.
  • caprylhydroxamic acid e.g., phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenethyl alcohol, ethyl lauroyl arginate (LAE), CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric
  • the antimicrobial preservative may comprise phenoxyethanol, benzyl alcohol, benzoic acid, a salt of benzoic acid (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT or a combination thereof. More than one antimicrobial preservative may be present or used in the compositions and methods of the present disclosure. Optimized amounts of the ether compound of the present application and the antimicrobial preservative may vary depending, for example, on the particular compound and preservative selected, the end use application, the desired level of preservation, the final properties of the product, and the like.
  • the ether compound is present in an amount effective to enhance the antimicrobial efficacy (e.g., enhance a desired preservative, antibacterial and/or antifungal effect) of the antimicrobial preservative in a product composition, such as a personal care, cosmetic or home care composition, (e.g., to meet or even exceed industry standards for antimicrobial efficacy) as compared to an equal amount of the antimicrobial preservative without the ether compound.
  • the amount of the ether compound may also be influenced by the desired multifunctional benefits, such as one or more of antioxidant, surfactant, humectant and/or chelating properties, as described herein.
  • R 1 , R 2 , or R 3 contain a —OH group (e.g., R 2 is –R 6 –OH, R 3 is —OH or –R 6 –OH, and R 1 is as described herein, preferably where R 1 is H, –R 6 –OH, alkyl or alkenyl as described herein, often H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl)), and the amount of the ether compound in the product composition provides at least a chelating property to the product composition.
  • R 1 is H, –R 6 –OH, alkyl or alkenyl as described herein, often H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl)
  • the amount of the ether compound in the product composition
  • R 1 , R 2 , or R 3 contain a —OH group (e.g., R 2 is –R 6 –OH, R 3 is —OH or –R 6 –OH, and R 1 is as described herein, preferably where R 1 is H, – R 6 –OH, alkyl or alkenyl as described herein, often H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl)), and the amount of the ether compound provides at least an antioxidant property to the product composition.
  • R 1 is H, – R 6 –OH, alkyl or alkenyl as described herein, often H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl)
  • the amount of the ether compound provides at least an antioxidant property to the product composition.
  • R 1 , R 2 , or R 3 contain a —OH group (e.g., R 2 is –R 6 –OH, R 3 is —OH or –R 6 –OH, and R 1 is as described herein, preferably where R 1 is H, –R 6 –OH, 8 Docket No.: P243 00001 ⁇ WO ⁇ PCT alkyl or alkenyl as described herein, often H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl)), and the amount of the ether compound provides at least an antioxidant property and a chelating property to the product composition, or at least an antioxidant property, a chelating property and a surfactant property to the production composition, or at least an antioxidant property, a chelating property, a surfactant property and a humectant property to the product composition.
  • R 1 is H, –R 6 –OH,
  • an amount of the ether compound of formula (I), such as an exemplary amount disclosed herein may be used in the product composition to increase the ⁇ M Trolox equivalents value of the composition (i.e., ⁇ mol Trolox/L sample) by at least 10%, more preferably by at least 15%, by at least 20% or by at least 25%, in particular by at least 30%, by at least 40% or by at least 50%, compared to the ⁇ M Trolox equivalents value of the composition in the absence of the ether compound of formula (I), where the
  • an amount of the ether compound of formula (I), such as an exemplary amount disclosed herein may be used in the product composition to increase the ⁇ M EDTA equivalents value of the composition (i.e., ⁇ mol EDTA/L sample) by at least 10%, more preferably by at least 15%, by at least 20% or by at least 25%, in particular by at least 30%, by at least 40% or by at least 50%, compared to the ⁇ M EDTA equivalents value of the composition in the absence of the ether compound of formula
  • the weight ratio of the ether compound to the antimicrobial preservative may range from about 1:50 to about 50:1, such as from about 1:20 to about 20:1, from about 1:15 to about 15:1, from about 1:10 to about 10:1, or from about 1:5 to about 5:1, although other ratios may be used.
  • the present application provides for the use of the presently disclosed ether compounds and antimicrobial preservatives in product compositions, such as personal care products, cosmetic products and home care products.
  • the ether compound and the antimicrobial preservative each may be present in the product composition in an amount ranging from about 0.001 wt%, from about 0.005 wt%, preferably from about 0.01 wt%, from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 5 wt%, preferably to about 3 wt%, to about 2 wt%, 9 Docket No.: P243 00001 ⁇ WO ⁇ PCT more preferably to about 1.5 wt%, or to about 1 wt%, based on the weight of the product composition, according to any combination of the foregoing lower and upper boundaries and any range therebetween.
  • the antimicrobial preservative is an isothiazolinone, preferably CMIT, MIT, BIT or a combination thereof.
  • the amount by weight of the ether compound may be substantially proportionally higher than the amount by weight of the antimicrobial preservative, such as a ratio of the ether compound to the antimicrobial preservative as high as 100:1, as high as 500:1, as high as 1000:1, as high as 5000:1, or higher.
  • the antimicrobial preservative is an isothiazolinone, preferably CMIT, MIT, BIT or a combination thereof.
  • the combined amount of the ether compound and antimicrobial preservative ranges from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 10 wt%, preferably to about 5 wt%, more preferably to about 3 wt%, to about 2 wt%, to about 1.5 wt% or to about 1 wt%, based on the weight of the product composition, according to any combination of the foregoing lower and upper boundaries and any range therebetween.
  • the combined amount may be from about 0.05 to about 7 wt%, such as from about 0.1 to about 5 wt%, from about 0.1 to about 4 wt%, from about 0.1 to about 3 wt%, or from about 0.1, from about 0.3 or from about 0.5 to about 3, to about 2 or to about 1 wt%, based on the weight of the product composition.
  • the ether compound and the antimicrobial preservative each is present in the product composition in an amount not exceeding about 2 wt%, preferably not exceeding about 1.5 wt% or not exceeding about 1 wt%, based on the weight of the product composition. Often each is present below 1 wt%.
  • the combined amount of the ether compound and antimicrobial preservative does not exceed about 3 wt% or does not exceed about 2 wt%, such as ranging from about 1.5 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.5 wt%), from about 1.2 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.2 wt%) or from about 1 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1 wt%), based on the weight of the product composition.
  • the ether compound may be combined with the antimicrobial preservative or added to a product composition in any suitable manner.
  • the ether compound may be added to a product composition prior to the addition of the antimicrobial preservative, concurrently with the addition of the antimicrobial preservative or after the addition of the antimicrobial preservative.
  • 10 Docket No.: P243 00001 ⁇ WO ⁇ PCT The ether compounds of the present disclosure can be incorporated into any number and variety of different personal care, cosmetic and home care products, particularly aqueous-based formulations, both water soluble or using water as a carrier, including emulsions (whether oil-in-water or water-in- oil).
  • Examples include, without limitation, household products and cleaners, fabric detergents, dish detergents, cleansers, soaps, bubble baths, disinfectants, deodorizers, hygiene compositions, infant care products, antimicrobial soaps, hand sanitizers, deodorants, antiperspirants, dermatological compositions, skin conditioners, skin moisturizers, anti-wrinkle formulations, sunscreens, tanning lotions, hair products, shampoos, shower gels, conditioners, shaving creams, etc.
  • Personal care products include, for example, products used in skincare, hair care, oral care, personal cleaning or hygiene, sun protection and other applications. Examples of personal care products include shampoos, conditioners, shower gels, liquid soaps, skin lotions, and liquids for any personal care wet wipe application.
  • ком ⁇ онентs may contain numerous and different ingredients depending on the end use application, that is, one or more additional ingredients suitable for use in a personal care, cosmetic or home care product composition.
  • a personal care composition comprises an antimicrobial preservative and an ether compound of formula (I), as described herein, and one or more additional ingredients suitable for use in a personal care composition.
  • a cosmetic composition comprises an antimicrobial preservative and an ether compound of formula (I), as described herein, and one or more additional ingredients suitable for use in a cosmetic composition.
  • the personal care or cosmetic composition may be, for example, any formulation for skin care, hair care, cosmetics, personal cleaning, hygiene, sun protection and other similar applications.
  • examples of such products include, without limitation, skin toners, skin cleansers, night creams, skin creams, shaving creams, skin lotions, makeup, mascara, lipstick, blush, gloss, eye-liner, makeup removers, sunscreens, lip balms, fragrances, massage oils, shampoos, conditioners, hair styling gels, hair reparatives, hair tonics, hair fixatives, hair mousses, bath and shower gels, liquid soaps, moisturizing sprays, bath additives, ophthalmic preparations, foaming soaps and body washes, liquids for any personal care wet wipe application, etc.
  • the personal care or cosmetic composition may contain numerous and different compatible ingredients, such as any of solvents, surfactants, emulsifiers, rheology modifiers, conditioners, emollients, skin care ingredients, moisturizers, thickeners, humectants, fillers, antioxidants, active ingredients, such as dermatologically active ingredients typically suited for topical application, fragrances and the like, and various mixtures thereof.
  • a home care composition comprises an antimicrobial preservative and an ether compound of formula (I), as described herein, and one or more additional ingredients suitable for use 11 Docket No.: P243 00001 ⁇ WO ⁇ PCT in a home care composition.
  • the home care composition may contain, for example, detergents, emulsifiers, surfactants, thickeners, gelling agents, bleaches, whiteners, deodorizers, enzymes, stabilizers, fragrances and the like, and various mixtures thereof.
  • detergents for example, detergents, emulsifiers, surfactants, thickeners, gelling agents, bleaches, whiteners, deodorizers, enzymes, stabilizers, fragrances and the like, and various mixtures thereof.
  • emulsifiers for example, surfactants, thickeners, gelling agents, bleaches, whiteners, deodorizers, enzymes, stabilizers, fragrances and the like, and various mixtures thereof.
  • the ether compounds of the present disclosure may be included in product compositions of a variety of different forms, for example, liquids, pastes, serums, hydrogels, creams, emulsions, lotions, gels, oils, wipes, ointments, semi-solid compositions, and aerosol sprays.
  • hair care products such as shampoos, hair conditioners, hair dyes, hair tonic, hair gel, hair dressings, hair grooming aids and other hair care preparations
  • shaving applications such as shaving cream, aftershave lotions, and other shaving applications
  • personal cleaners for the body and hands such as liquid bath soaps and detergents
  • fragrance preparations such as perfumes, after bath splashes, and other similar fragrant preparations
  • skin care products such as moisturizers, creams, and lotions and other similar skin care products, make-up products, such as mascara, base foundations and the like
  • formulations used to saturate wipes used for personal cleaning and hygiene for example, baby wipes, wet toilet wipes, make-up removal wipes and exfoliating wipes the like, or wet wipe formulations for home care.
  • the product composition has a pH ranging from about 3.0, from about 4.0, from about 5.0, from about 5.5, or from about 6.0 to about 11, such as from about 3.0 to about 10, from about 4.0 to about 8.5, or from about 5.0 to about 7.5.
  • pH values or ranges refer to pH at room temperature (20-25 °C).
  • the selected pH will vary depending, for example, on the particular end use application.
  • the personal care or cosmetic composition preferably has a pH ranging from about 3.0 or from about 4.0 to about 8.0, such as from about 4.0 or from about 5.0 to about 7.5 or to about 7.0.
  • the home care composition preferably has a pH ranging from about 3.0 to about 11, such as from about 4.0 or from about 5.0 to about 10, or from about 5.0 or from about 6.0 to about 9.0, to about 8.0, to about 7.5 or to about 7.0.
  • a method of providing antimicrobial activity to a personal care, cosmetic or home care product composition comprises adding to the composition an antimicrobial preservative and an ether compound of formula (I).
  • the present disclosure is not limited to any particular technique for preparing a product composition, and the antimicrobial preservative and the ether compound of formula (I) may be added to a product composition in any suitable manner.
  • the antimicrobial preservative and the ether 12 Docket No.: P243 00001 ⁇ WO ⁇ PCT compound of formula (I) can be applied to a product formulation as a mixture or applied individually to the formulation at the same time or in any order.
  • the present disclosure provides for the use of an ether compound of formula (I) as described herein for enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition.
  • a method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) as described herein.
  • the antimicrobial efficacy is enhanced as compared to an equal amount of the antimicrobial preservative without the ether compound.
  • a method of reducing the minimum amount of an antimicrobial preservative needed for preservation activity in a personal care, cosmetic or home care product composition comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) as described herein, wherein after said combining or mixing with the ether compound, the minimum amount of the antimicrobial preservative needed for preservation activity in the product composition is less than if the antimicrobial preservative was used alone.
  • ether compound of formula (I) the antimicrobial preservative, exemplary ratios and amounts, product compositions and ingredients, etc. also apply to the methods of the present disclosure.
  • Various different microorganisms may be controlled in accordance with the present disclosure.
  • a combination of an antimicrobial preservative and the ether compound of the present disclosure preferably controls gram positive bacteria, gram negative bacteria, and fungi, among other microorganisms.
  • Non-limiting examples include Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa, Escherichia coli, Enterobacter gergoviae, Klebsiella pneumoniae, Burholderia cepacia, Pseudomonas putida, Candida albicans, Aspergillus brasiliensis, and mixtures thereof.
  • an antimicrobial effect may be demonstrated by various suitable antimicrobial effectiveness tests.
  • the antimicrobial preservative and the ether compound of formula (I) when added to a product composition, provide an antimicrobial effect according to the challenge test procedures in the below Examples achieving a passing growth rating according to the criteria associated with Table 7 and the associated description herein.
  • an antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) as described herein, preferably wherein the antimicrobial preservative and the ether compound of formula (I) collectively constitute from 50 to 100 wt% of the active ingredients in the antimicrobial composition, further preferably wherein the antimicrobial preservative comprises an isothiazolinone (e.g., CMIT, MIT, BIT, combinations 13 Docket No.: P243 00001 ⁇ WO ⁇ PCT thereof), an alkylhydroxamic acid and/or salt thereof (e.g., hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid, salts thereof, combinations thereof, preferably caprylhydroxamic acid and/or a salt thereof), an aromatic aldehyde (e.g., cinnamic aldehyde), an alcohol (e.g.
  • the antimicrobial preservative may comprise an alkylhydroxamic acid and/or salt thereof (preferably, hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid and/or salt thereof or combination thereof, particularly caprylhydroxamic acid and/or salt thereof), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, 1,2- pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., caprylyl glycol), bronopol, ethylhexylglycerin, chlorphenesin, CMIT,
  • the antimicrobial preservative comprises an isothiazolinone, an aromatic aldehyde, an aromatic alcohol, an aromatic ether, an organic acid, a salt or ester of an organic acid, a pyrithione, ethyl lauroyl arginate (LAE) or a combination thereof.
  • the antimicrobial preservative may comprise caprylhydroxamic acid, phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenethyl alcohol, ethyl lauroyl arginate (LAE), CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4- dienoic acid, 4-hydroxybenzoic acid, an ester or salt of said organic acids (e.g., sodium benzoate, potassium sorbate and the like), or a combination thereof.
  • caprylhydroxamic acid e.g., phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenethyl alcohol, ethyl lauroyl arginate (LAE), CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric
  • the antimicrobial preservative may comprise phenoxyethanol, benzyl alcohol, benzoic acid, a salt of benzoic acid (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT or a combination thereof.
  • benzoic acid e.g., sodium benzoate
  • ethyl lauroyl arginate CMIT, MIT, BIT or a combination thereof.
  • the antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) in a combined amount that is a majority (>50 wt%) of the active ingredients 14 Docket No.: P243 00001 ⁇ WO ⁇ PCT in the antimicrobial composition, such as at least 60 wt% or at least 70 wt%, preferably at least 80 wt%, more preferably at least 85 wt%, at least 90 wt%, at least 95 wt%, at least 96 wt%, at least 97 wt%, at least 98 wt% or at least 99 wt%, based on the total weight of active ingredients in the antimicrobial composition.
  • the antimicrobial composition often contains from about 60 to 100 wt%, preferably from about 65 to 100 wt%, from about 70 to 100 wt%, from about 75 to 100 wt%, from about 80 to 100 wt%, from about 85 to 100 wt%, from about 90 to 100 wt%, or from about 95 or from about 97 to 100 wt%, of an antimicrobial preservative and an ether compound of formula (I) combined, based on the total weight of active ingredients in the antimicrobial composition.
  • the antimicrobial composition comprises active ingredients consisting essentially of, or in further embodiments consists of, an antimicrobial preservative and an ether compound of formula (I).
  • the antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) in a combined amount of 50 to 100 wt% of the total weight of the antimicrobial composition, typically a majority (>50 wt%) of the antimicrobial composition, such as at least 60 wt% or at least 70 wt%, preferably at least 80 wt%, more preferably at least 85 wt%, at least 90 wt%, at least 95 wt%, at least 96 wt%, at least 97 wt%, at least 98 wt% or at least 99 wt%, based on the total weight of the antimicrobial composition.
  • a majority (>50 wt%) of the antimicrobial composition such as at least 60 wt% or at least 70 wt%, preferably at least 80 wt%, more preferably at least 85 wt%, at least 90 wt%, at least 95 wt%, at least 96 wt%, at least 97
  • the antimicrobial composition often contains from about 60 to 100 wt%, preferably from about 70 to 100 wt%, from about 75 to 100 wt%, from about 80 to 100 wt%, from about 85 to 100 wt%, from about 90 to 100 wt%, or from about 95 or about 97 to 100 wt%, of an antimicrobial preservative and an ether compound of formula (I) combined, based on the total weight of the antimicrobial composition.
  • the antimicrobial composition consists essentially of, or in further embodiments consists of, an antimicrobial preservative and an ether compound of formula (I).
  • the antimicrobial composition may, but need not, comprise one or more added solvents or carriers.
  • the solvent or carrier typically constitutes from about 10 wt%, from about 20 wt% or from about 30 wt% to about 90 wt%, to about 85 wt%, to about 80 wt%, to about 70 wt%, to about 60 wt% or to about 50 wt%, based on the total weight of the antimicrobial composition.
  • Solvents or carriers may be chosen according to their compatibility or suitability for a desired end application or end product formulation, such as in a personal care, cosmetic or home care composition, (e.g., a cosmetically acceptable solvent or carrier).
  • Suitable solvents and carriers include, but are not limited to, water, water-miscible solvents, C 1 -C 4 alcohols, C 1 -C 4 diols (e.g., glycols), glycerin and the like.
  • the antimicrobial composition may, but need not, contain one or more excipients, typically in minor quantities. Excipients may similarly be chosen according to their compatibility or suitability for a desired end application or end product formulation, such as in a personal care, cosmetic or home care composition, (e.g., a cosmetically acceptable excipient).
  • excipients include, but are not 15 Docket No.: P243 00001 ⁇ WO ⁇ PCT limited to, a dispersant, solubilizer, buffer, and/or stabilizer.
  • the antimicrobial composition may comprise, for example, from 0 to about 10 wt% of one or more excipients, such as from about 0.001 wt%, from about 0.01 wt%, from about 0.05 wt% or from about 0.1 wt% to about 5 wt%, to about 3 wt%, or to about 1 wt%, based on the total weight of the antimicrobial composition.
  • the amount of excipients may range from 0 to about 5 wt%, from 0 to about 3 wt% from about 0.01 to about 5 wt%, from about 0.1 to about 5 wt%, from about 0.01 to about 3 wt%, from about 0.1 to about 3 wt%, from about 0.01 to about 1 wt%, or from about 0.1 to about 1 wt%.
  • the antimicrobial composition may comprise a combined amount of an antimicrobial preservative and an ether compound of formula (I) of from about 10 to 100 wt%, such as from about 15 wt% or from about 20 wt%, from about 30 wt%, from about 40 wt%, from about 50 wt% or from about 60 wt% to 100 wt%, to about 99 wt%, to about 97 wt%, to about 95 wt%, to about 90 wt%, to about 80 wt%, or to about 70 wt%, based on the total weight of the antimicrobial composition; optionally one or more solvents or carriers in an amount from 0 to about 90 wt%, such as from about 10 wt%, from about 20 wt% or from about 30 wt% to about 90 wt%, to about 85 wt%, to about 80 wt%, to about 70 wt%, to about 60 wt%, to about 50 w
  • the combined amount of an antimicrobial preservative and an ether compound of formula (I) may be from about 10 wt% to about 90 wt%, from about 20 wt% to about 80 wt%, or from about 30 wt% to about 70 wt%, and the amount of solvent or carrier may be from about 10 wt% to about 90 wt%, from about 20 wt% to about 80 wt%, or from about 30 wt% to about 70 wt%, optionally further comprising one or more excipients.
  • the antimicrobial composition consists essentially of, or in further embodiments consists of, an antimicrobial preservative, an ether compound of formula (I), optionally one or more solvents or carriers and optionally one or more excipients.
  • the antimicrobial composition can be added to a product composition in an amount effective to achieve a desired level of antimicrobial efficacy in or preservation of the product composition. It shall be understood that the descriptions herein with respect to the ether compound of formula (I), the antimicrobial preservative, exemplary ratios and amounts, product compositions and ingredients, etc. also apply to the antimicrobial composition of the present disclosure and/or its addition to product compositions, particularly personal care, cosmetic or home care product compositions.
  • Embodiment 1 An antimicrobial composition comprising an antimicrobial preservative and an ether compound of formula (I) , alkenyl, –R 6 –OH, or –R 8 –O–R 9 ;
  • R 2 is –C 1 -C 6 alkyl, –C 2 -C 6 alkenyl, –R 6 –OH, –O–R 7 , or –R 8 –O–R 9 ;
  • R 3 is –OH, –R 6 –OH, –O–R 7 or –R 8 –O–R 9 ;
  • R 4 is –C 2 -C 5 alkenyl; and
  • R 5 is H, –C 1 -C 5 alkyl, or –C 2 -C 5 alkenyl; and, with respect to R 1 , R 2 and R 3 independently of one another, R 6 is –C 1
  • Embodiment 2 A product composition comprising the ether compound of formula (I) as described in Embodiment 1 and an antimicrobial preservative, wherein the product composition is chosen from personal care products, cosmetic products, and home care products.
  • Embodiment 3 A method of providing antimicrobial activity to a product composition, comprising adding to the product composition an antimicrobial preservative and the ether compound of formula (I) as described in Embodiment 1, and the product composition is chosen from personal care products, cosmetic products, and home care products.
  • Embodiment 4 A method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, comprising adding to the product composition the ether compound of formula (I) as described in Embodiment 1, wherein the product composition is chosen from personal care products, cosmetic products, and home care products.
  • Embodiment 5 A method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, comprising combining or mixing the antimicrobial preservative with an ether compound as described in Embodiment 1, wherein the product composition is chosen from personal care products, cosmetic products, and home care products.
  • Embodiment 6 Use of the ether compound of formula (I) as described in Embodiment 1 for enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, wherein the product composition is chosen from personal care products, cosmetic products, and home care products. 17 Docket No.: P243 00001 ⁇ WO ⁇ PCT Embodiment 7: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-6, wherein at least one of R 1 , R 2 or R 3 contains a –OH group.
  • Embodiment 8 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-7, wherein at least one of R 1 , R 2 or R 3 contains a –OH group, and at least one other of R 1 , R 2 or R 3 contains an ether group.
  • Embodiment 9 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-8, wherein at least two of R 1 , R 2 , or R 3 contain a –OH group.
  • Embodiment 10 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-7, wherein R 1 , R 2 , and R 3 each contains a –OH group.
  • Embodiment 11 The antimicrobial composition, product composition, method or use according to one of Embodiments 1-10, wherein the total number of carbons in R 1 , R 2 , and R 3 combined is no more than 12, preferably no more than 8 or no more than 6.
  • Embodiment 12 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-11, wherein R 1 in formula (I) is H, –R 6 –OH, –R 8 –O–R 9 , –C 1 -C 4 alkyl or – C 2 -C 4 alkenyl; or R 1 is H, –R 6 –OH, –C 1 -C 4 alkyl or –C 2 -C 4 alkenyl; or R 1 is H, –R 6 –OH or –C 1 -C 4 alkyl; or R 1 is H, –C 1 -C 4 alkyl or –C 2 -C 4 alkenyl.
  • Embodiment 13 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-9, 11 and 12, wherein R 2 in formula (I) is –C 1 -C 4 alkyl or –C 2 -C 4 alkenyl.
  • Embodiment 14 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-12, wherein R 2 in formula (I) is R 6 –OH, –O–R 7 , or –R 8 –O–R 9 .
  • Embodiment 15 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-12 and 14, wherein R 2 is R 6 –OH, and R 3 is —OH or –R 6 –OH.
  • Embodiment 16 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-9, 11, 12, and 14, wherein R 2 is O–R 7 or –R 8 –O–R 9 , and R 3 is –OH or – R 6 –OH, preferably wherein R 2 is –R 8 –O–R 9 , and further preferably wherein R 1 is H, –R 6 –OH, –C 1 -C 4 alkyl or –C 2 -C 4 alkenyl or R 1 is H, –R 6 –OH or –C 1 -C 4 alkyl.
  • Embodiment 17 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-16, wherein R 4 in formula (I) is C 2 -C 3 alkenyl, preferably C 2 alkenyl.
  • Embodiment 18 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-17, wherein R 5 in formula (I) is H.
  • Embodiment 19 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-18, wherein R 6 is –C 1 -C 4 alkylene or –C 3 -C 4 alkenylene, R 7 is –C 1 -C 4 alkyl or –C 3 -C 4 alkenyl, R 8 is –C 1 -C 3 alkylene or –C 3 alkenylene, and R 9 is –C 1 -C 3 alkyl or –C 3 alkenyl; or 18 Docket No.: P243 00001 ⁇ WO ⁇ PCT R 6 is –C 1 -C 6 (preferably –C 1 -C 4 ) alkylene, R 7 is –C 1 -C 6 (preferably –C 1 -C 4 ) alkyl, R 8 is –C 1 -C 5 (preferably –C 1 -C 3 ) alkylene, and R 9 is –C 1 -C 5 (preferably –C 1 -
  • Embodiment 20 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-6, wherein the ether compound of formula (I) is chosen from 2-(Allyloxymethyl)-2-ethyl-1,3-propanediol, 2,2-bis(allyloxymethyl)-2-ethylpropanediol, 3-allyloxy-1,2-propanediol, 2,2-bis(hydroxymethyl)-1,3-propanediol allyl ether, and a combination thereof.
  • the ether compound of formula (I) is chosen from 2-(Allyloxymethyl)-2-ethyl-1,3-propanediol, 2,2-bis(allyloxymethyl)-2-ethylpropanediol, 3-allyloxy-1,2-propanediol, 2,2-bis(hydroxymethyl)-1,3-propanediol allyl ether, and a combination thereof.
  • Embodiment 21 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-20, wherein the ratio of the antimicrobial preservative to the ether compound of formula (I) ranges from about 1:50 to about 50:1, preferably from about 1:20 to about 20:1, from about 1:15 to about 15:1, from about 1:10 to about 10:1, or from about 1:5 to about 5:1.
  • Embodiment 22 The antimicrobial composition of any one of Embodiments 1-21, wherein the antimicrobial composition contains greater than or equal to about 50 wt% of the antimicrobial preservative and the ether compound of formula (I) combined, based on the total weight of active ingredients in the antimicrobial composition, preferably from about 60 to 100 wt%, from about 70 to 100 wt%, from about 75 to 100 wt%, from about 80 to 100 wt%, from about 85 to 100 wt%, from about 90 to 100 wt%, or from about 95 or from about 97 to 100 wt%, based on the total weight of active ingredients in the antimicrobial composition.
  • Embodiment 23 The antimicrobial composition of any one of Embodiments 1-22, wherein the antimicrobial composition comprises active ingredients consisting essentially of, or in further embodiments consisting of, the antimicrobial preservative and the ether compound of formula (I).
  • Embodiment 24 The antimicrobial composition of any one of Embodiments 1-23, wherein the antimicrobial composition contains greater than or equal to about 50 wt% of the antimicrobial preservative and the ether compound of formula (I) combined, based on the total weight of the antimicrobial composition, preferably from about 60 to 100 wt%, from about 70 to 100 wt%, from about 75 to 100 wt%, from about 80 to 100 wt%, from about 85 to 100 wt%, from about 90 to 100 wt%, or from about 95 or from about 97 to 100 wt%, based on the total weight of the composition.
  • Embodiment 25 The antimicrobial composition of any one of Embodiments 1-24, wherein the antimicrobial composition consists essentially of, or in further embodiments consists of, the antimicrobial preservative and the ether compound of formula (I).
  • Embodiment 26 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises an isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), an alkylhydroxamic acid and/or salt thereof (e.g., 19 Docket No.: P243 00001 ⁇ WO ⁇ PCT hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid, salts thereof, combinations thereof, preferably caprylhydroxamic acid and/or a salt thereof), an aromatic aldehyde (e.g., cinnamic aldehyde
  • Embodiment 27 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises an isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), an aromatic aldehyde (e.g., cinnamic aldehyde), an aromatic alcohol (e.g., benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic alcohol, a phenolic compound, such as hydroxyacetophenone, combinations thereof), an aromatic ether (e.g., phenoxyethanol), an organic acid (e.g., benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, combinations thereof), a salt or ester of an organic acid (e.g., esters and/or salts of the above organic acids, such as
  • Embodiment 28 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises an alkylhydroxamic acid and/or salt thereof (preferably, hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid and/or salt thereof or combination thereof, particularly caprylhydroxamic acid and/or salt thereof), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., caprylyl glycol),
  • Embodiment 29 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises caprylhydroxamic acid, phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenethyl alcohol, ethyl lauroyl arginate (LAE), CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, an ester or salt of said organic acids (e.g., sodium benzoate, potassium sorbate and the like), or a combination thereof; or the antimicrobial preservative comprises phenoxyethanol, benzyl alcohol, benzoic acid, a salt of benzoic acid (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT or a
  • Embodiment 30 The product composition, method or use according to any one of Embodiments 2-21 and 26-29, wherein the ether compound of formula (I) is present in the product composition in an amount ranging from about 0.05 wt%, preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 10 wt%, preferably to about 5 wt%, more preferably to about 3 wt%, to about 2 wt%, in particular to about 1.5 wt%, or to about 1 wt%, based on the total weight of the product composition.
  • Embodiment 31 The product composition, method or use according to any one of Embodiments 2-21 and 26-30, wherein the ether compound of formula (I) and the antimicrobial preservative are each present in the product composition in an amount ranging from about 0.05 wt%, preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 5 wt%, preferably to about 3 wt%, to about 2 wt%, more preferably to about 1.5 wt%, or to about 1 wt%, based on the total weight of the product composition.
  • Embodiment 32 The product composition, method or use according to any one of Embodiments 2-21 and 26-31, wherein the ether compound of formula (I) and the antimicrobial preservative are present in the product composition in a combined amount of from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 10 wt%, preferably to about 5 wt%, more preferably to about 3 wt%, to about 2 wt%, to about 1.5 wt% or to about 1 wt%, based on the weight of the product composition.
  • Embodiment 33 The product composition, method or use according to any one of Embodiments 2-21 and 26-32, wherein the ether compound of formula (I) and the antimicrobial preservative each is present in the product composition in an amount not exceeding 2 wt%, preferably not exceeding 1.5 wt% or not exceeding 1 wt%, based on the weight of the product composition.
  • Embodiment 34 The product composition, method or use according to any one of Embodiments 2-21 and 26-33, wherein the combined amount of the ether compound of formula (I) and the antimicrobial preservative does not exceed 3 wt%, preferably does not exceed 2 wt%, such as from about 1.5 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.5 wt%), from about 1.2 wt% or 21 Docket No.: P243 00001 ⁇ WO ⁇ PCT less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.2 wt%) or from about 1 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1 wt%), based on the weight of the product composition.
  • P243 00001 ⁇ WO ⁇ PCT less e.g., from about 0.1 wt% or from about 0.3 w
  • Embodiment 35 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-34, wherein the ether compound of formula (I) has one or more properties chosen from antioxidant, surfactant, humectant and chelating properties.
  • Embodiment 36 The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-12, wherein at least two of R 1 , R 2 , or R 3 in formula (I) contain a —OH group (e.g., where R 2 is –R 6 –OH and R 3 is —OH or –R 6 –OH, preferably wherein R 1 is H, –R 6 –OH, alkyl or alkenyl or is H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl)), and the ether compound of formula (I) has at least an antioxidant property, at least a chelating property, or at least an antioxidant property and a chelating property, wherein the antioxidant property is a ⁇ M Trolox equivalents (TE) value (i.e., ⁇ mol Trolox/L sample) of at least 25 ⁇ M TE, more preferably
  • Embodiment 37 The product composition, method or use according to any one of Embodiments 2-12, wherein at least two of R 1 , R 2 , or R 3 in formula (I) contain a –OH group (e.g., where R 2 is –R 6 –OH and R 3 is —OH or –R 6 –OH, preferably wherein R 1 is H, –R 6 –OH, alkyl or alkenyl or is H, –R 6 –OH or –C 1 -C 6 alkyl or –C 1 -C 4 alkyl (e.g., methyl or ethyl)) and the amount of the ether compound of formula (I) (e.g., an amount according to any one or combination of Embodiments 30-34) provides at least an antioxidant property, at least a chelating property, or at least an antioxidant property and a chelating property to the product composition, wherein the antioxidant property provided to the product composition is an increase in the ⁇ M Trolox equivalents value
  • Embodiment 38 The product composition, method or use according to any one of Embodiments 2-21 and 26-37, wherein the product composition is formulated as a liquid, paste, serum, hydrogel, cream, emulsion, lotion, gel, oil, wipe, ointment, semi-solid composition, or aerosol spray.
  • Embodiment 39 The product composition, method or use according to any one of Embodiments 2-21 and 26-38, wherein the product composition is a personal care or cosmetic product chosen from shampoos, conditioners, shower gels, liquid soaps, skin lotions, liquids for a wet wipe, face creams, hair treatments, makeup, and makeup removers.
  • alkyl means a monovalent linear or branched saturated hydrocarbon having the specified number of carbons.
  • alkylene means a divalent linear or branched saturated hydrocarbon having the specified number of carbons.
  • alkenyl means a monovalent linear or branched hydrocarbon having at least one carbon-carbon double bond.
  • alkenylene means a divalent linear or branched hydrocarbon having at least one carbon-carbon double bond.
  • comprising means the presence of the stated features, integers, steps, or components as referred to in the claims, but does not preclude the presence or addition of one or more other features, integers, steps, components or groups thereof.
  • the term “comprising” is intended to include embodiments encompassed by the terms “consisting essentially of” and “consisting of,” unless the context dictates otherwise.
  • the term “about” modifying the quantity of an ingredient or reactant employed refers to variation in the numerical quantity that can occur, for example, through typical measuring and liquid handling procedures used for making concentrates or use solutions in the real world; through inadvertent error in these procedures; through differences in the manufacture, source, or purity of the ingredients employed to make the compositions or carry out the methods; and the like. Where present, all ranges are inclusive and combinable. For example, when a range of “1 to 5” is recited, the recited range should be construed as including ranges “1 to 4”, “1 to 3”, “1-2”, “1-2 & 4- 5”, “1-3 & 5”, and the like.
  • EXAMPLES demonstrate that the ether compounds of the present disclosure, when incorporated into various product formulations, surprisingly improved the preservation efficacy of traditional and soft antimicrobial preservatives, including, but not limited to, phenoxyethanol, sodium benzoate, benzyl alcohol, Ethyl lauroyl arginate (LAE), and 2-methyl-4-isothiazolin-3-one (MIT), against a full spectrum of different bacteria and fungi, thereby enabling reduction in required traditional or soft preservative levels for protecting such products against microbial growth.
  • traditional and soft antimicrobial preservatives including, but not limited to, phenoxyethanol, sodium benzoate, benzyl alcohol, Ethyl lauroyl arginate (LAE), and 2-methyl-4-isothiazolin-3-one (MIT)
  • Ether compounds of the present disclosure further surprisingly (i) showed significant antioxidant properties based on determined Trolox equivalent values and provided antioxidant properties to product compositions; (ii) showed humectant properties as demonstrated by reduced water activity (measured by Rotronic Water Activity Meter) comparable to known moisturizing ingredients such as ethyl hexyl glycerin; (iii) reduced the surface tension after dosing into water, demonstrating surfactant properties; and (iv) showed significant chelating properties based on determined EDTA equivalent values.
  • Compounds representative of the presently disclosed ether compounds and used in the following experimental examples are shown in Table 1. 24 Docket No.: P243 00001 ⁇ WO ⁇ PCT Table 1.
  • the presently disclosed ether compounds were tested alone and in combination with certain antimicrobial preservatives in various product formulations.
  • the compounds were dosed and mixed thoroughly at room temperature into the different compositions, including a lotion with carbomer (leave-on, Table 2), and a serum composition with xanthan gum (leave-on , Table 3), a body wash formulation (rinse- off , Table 4), and a cream formulation (leave-on, Table 5).
  • Table 2 shows an exemplary composition for carbomer-based anionic lotion compositions.
  • Carbomers are commonly used as a synthetic rheological modifier in personal care products.
  • the composition below was made by heating the aqueous (A) and oil (B) phases separately to 75-80 °C.
  • Representative Serum Composition with Xanthan Gum Ingredients INCI Name WT 0 Docket No.: P243 00001 ⁇ WO ⁇ PCT XIAMETER PMX-200 Dimethicone 2.00 Silicone Fluid 100 cSt ACULYN 88 and water in a beaker and then adding STEOL 230 and AMPHOSOL CA. The solution was mixed with an overhead mixer. Triethanolamine was used to adjust the final pH to 6.8. Table 4.
  • Representative Body Wash Formulation Ingredients INCI Name WT % Deionized water Deionized water 70.5 Ta by heating the aqueous (A) and oil (B) phases separately to 75-80 °C.
  • a mixed bacterial inoculum was prepared using 24-hour cultures of the test bacteria (Table 6) grown in trypticase soy broth (TSB). Equal volumes of the bacterial test strains were combined and diluted one to ten in phosphate buffer to obtain an inoculum of approximately 5 x 10 7 to 5 x 10 8 colony forming units per mL (cfu/mL). The test samples were inoculated with 1% of the mixed bacterial inoculum.
  • a mixed fungal inoculum was prepared using cell suspensions of the yeast Candida albicans ATCC # 10231 and the mold Aspergillus brasiliensis ATCC #16404 in phosphate buffer.
  • the number of microorganisms added to each sample was determined by a standard Most Probable Number (MPN) determination in Trypticase Soy Broth (TSB) for bacteria and Potato Dextrose Broth (PDB) for fungi. Samples were incubated at 25 °C for the test duration of four weeks. Samples were monitored for bacterial and fungal contamination after 2, 7, 14, 21, and 28 days. Samples challenged with bacteria were streak-plated onto Trypticase Soy Agar (TSA) and incubated at 30 °C for 24 hours. Samples challenged with fungi were streak-plated onto Potato Dextrose Agar (PDA) and incubated at 25 °C for 7 days.
  • MPN Most Probable Number
  • CFU/g colony forming units per gram
  • Table 7 represents the growth score. A rating of excellent, good, and adequate were all considered to be a pass for the challenge test. As is used by various challenge test methods, the passing criteria was more stringent for bacteria than for fungi. A rating of 2, 3, or 4 at 21 and/or 28 28 Docket No.: P243 00001 ⁇ WO ⁇ PCT days was considered a failure for bacteria. For fungi, a rating of 2 at 21 and/or 28 days was considered a pass. Table 7. Growth Score Used to Determine CFU/mL in Test Samples.
  • Example 1A A representative leave-on lotion formulation was made according to Table 2. As shown in Table 8, none of the lotion formulations passed the challenge test when dosed with either phenoxyethanol (POE), benzyl alcohol (BA) or the compounds in Table 1 alone. However, when dosed with a combination of phenoxyethanol or benzyl alcohol and the respective Compounds 1 to 4, the lotion formulations showed significantly enhanced antimicrobial properties against both bacteria and fungi, each achieving a passing rating in the challenge testing.
  • phenoxyethanol POE
  • BA benzyl alcohol
  • Table 1 the lotion formulations showed significantly enhanced antimicrobial properties against both bacteria and fungi, each achieving a passing rating in the challenge testing.
  • This example demonstrates the enhanced efficacy of soft preservatives, such as phenoxyethanol and benzyl alcohol, when combined with the ether compounds of the present disclosure, and advantageously so such that efficacious antimicrobial activity can be achieved at reduced dosing levels of soft preservatives (e.g., 0.3 to 0.5% or to 0.4%).
  • soft preservatives such as phenoxyethanol and benzyl alcohol
  • Table 10 Challenge test data – body wash formulation Bacteria growth Fungi growth rating rating rating
  • Traditional isothiazolinone preservatives such as 2-methyl-4-isothiazolin-3-one (i.e., methylisothiazolinone, MIT), are commonly used to protect personal and home care products from bacteria.
  • Table 11 shows an example of using Compound 1 in Table 1 to enhance the antimicrobial performance of MIT in a representative lotion formulation (Table 2).
  • Table 2 When used alone at either 5 or 10 ppm, MIT failed to preserve the lotion formulation against bacteria.
  • Table 11 When MIT was combined with Compound 1 dosed at a level of 0.5%, the preservation performance of MIT was significantly enhanced, and the lotion formulation was successfully preserved against bacteria.
  • Table 11 Challenge test data – lotion formulation comprising carbomer 32 Docket No.: P243 00001 ⁇ WO ⁇ PCT Bacteria growth rating Sample and Dosing (wt%) D7 D14 D21 D28 Result Ethyl lauroyl arginate (LAE) is a cationic preservative commonly used in food, home and personal care applications.
  • LAE Ethyl lauroyl arginate
  • Table 12 shows an example of using Compound 1 in Table 1 to enhance the antimicrobial performance of LAE in a nonionic cream formulation (Table 5).
  • Table 5 When used alone from 1000 to 4000 ppm, LAE failed to preserve the lotion formulation against bacteria.
  • Table 12 Challenge test data – nonionic cream formulation Bacteria growth rating Example 1F Ethylhexylglycerin (EHG) and pentylene glycol (1,2-pentanediol) are commercially available multifunctional ingredients often used to enhance the antimicrobial performance of soft preservatives, such as phenoxyethanol.
  • Table 13 shows an example of using Compound 1 in Table 1 to enhance the antimicrobial performance of phenoxyethanol, as compared against EHG and pentylene glycol as commercial benchmarks, in a representative lotion formulation (Table 2).
  • Compound 1 exhibited 33 Docket No.: P243 00001 ⁇ WO ⁇ PCT superior antimicrobial enhancement of POE as compared to either of ethylhexylglycerin or pentylene glycol (Table 13).
  • Table 13 shows an example of using Compound 1 in Table 1 to enhance the antimicrobial performance of phenoxyethanol, as compared against EHG and pentylene glycol as commercial benchmarks, in a representative lotion formulation (Table 2).
  • Compound 1 exhibited 33 Docket No.: P243 00001 ⁇ WO ⁇ PCT superior antimicrobial enhancement of POE as compared to either of ethylhexylglycerin or pentylene glycol (Table 13).
  • Table 13 shows an example of using Compound 1 in Table 1 to enhance the antimicrobial performance
  • micellar water composition was made by adding all the ingredients into a beaker and heating the ingredient mixture to 75 ⁇ 80 °C. The final product was cooled to room temperature and pH was adjusted to 5-5.5 with citric acid solution. Sample compounds were dosed into the compositions at the desired weight percent by using a speed mixer. Table 14.
  • Hydrogel Composition with Xanthan Gum Ingredients INCI Name WT % 34 Docket No.: P243 00001 ⁇ WO ⁇ PCT Xanthan gum Xanthan gum 0.50 Ingredients INCI Name WT % Water Aqua 92.95 0 ⁇ M) were used as the calibration curve for quantifying the antioxidant properties.
  • the absorbance of the Trolox and the multifunctional additives were measured in triplicates using the Multimode Microplate Reader, BioTek Synergy H1, at a wavelength of 405 nm.
  • Table 16 summarizes the intrinsic antioxidant property of each of Compounds 1-4 based on the Trolox equivalents values determined using the Activated ABTS test.
  • the alkenyl (e.g., allyl) ether compounds of the present disclosure exhibit significant antioxidant properties (i.e., in this Example, Compounds 1, 3 and 4).
  • pentylene glycol a preservative or preservative enhancer commonly used in personal care and cosmetic products
  • benzyl alcohol a soft preservative commonly used in personal care and cosmetic products
  • Trolox equivalents (calculated from a Trolox calibration curve) Sample Ingredient and weight precent ⁇ M Trolox equivalents ) 35 Docket No.: P243 00001 ⁇ WO ⁇ PCT Compound 2 2,2-Bis(allyoxymethyl)-2-ethylpropanediol 0 ⁇ 6 Compound 3 Pentaerythritol allyl ether 150 ⁇ 2 Compou speed mixer.
  • the hydrogel compositions were all diluted by the assay buffer at 5-fold dilution to make the final solution fully transparent, while running the Activated ABTS Assay (i.e., Cat# AOX- 14, instruction manual ZBM0123.00, April 2021) to ensure the composition (e.g., translucency) did not contribute to the antioxidant properties.
  • micellar water showed antioxidant property with a Trolox equivalents value of 72 ⁇ 1 ⁇ M because of the antioxidant property of the ingredients (such as propylene glycol, disodium EDTA, and panthenol) used in the composition (Table 15).
  • the micellar water After being dosed with Compound 1, the micellar water showed an increase of Trolox equivalents values as the dosing level increased. This further demonstrates the antioxidant benefits associated with the presently disclosed ether compounds.
  • Table 18 Trolox equivalents (calculated from a Trolox calibration curve) of the micellar water sample.
  • the parameter was the measure of unbound water molecule in a system and provided a measure of the ability of the system to adsorb water and act as humectant.
  • Compounds 1 to 4 in Table 1 showed comparable water activity reduction at 10 wt% as compared against the two benchmarks glycerin and 2-ethylhexylglycerin.
  • glycerin showed the largest reduction of the water activity as a result of solubility limitations of the 38 Docket No.: P243 00001 ⁇ WO ⁇ PCT other samples.
  • This example demonstrates that the ether compounds of the present disclosure can be used as a humectant, particularly at dosing levels at or less than 10%. Table 21.
  • the Cupric Ion Chelating activity was determined as the percent of total PV over the Cu(II) binding.
  • Ethylenediaminetetraacetic acid (EDTA) a well-known chelating agent, was used as a positive control.
  • a series of EDTA with 7 different concentrations from 0 to 1000 ⁇ M were prepared and their corresponding absorbance measured and used as the calibration curve (Cupric ion chelating (%) vs. EDTA concentration).
  • Percent Cupric ion chelating was determined applying the following calculations and equation 1.
  • the background absorbance value was determined by averaging the absorbance values of the three background wells (no CuSO 4 or sample). The average background absorbance was then subtracted from all of the sample absorbance values.

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Abstract

The present disclosure relates to certain ether compounds as described herein as new multifunctional boosters for enhancing the activity of antimicrobial preservatives and applications thereof in personal care products, cosmetic products and home care products.

Description

Docket No.: P243 00001‐WO‐PCT  TITLE Multifunctional Boosters for Antimicrobial Preservatives and Applications Thereof FIELD OF INVENTION The present invention relates generally to multifunctional boosters to enhance the antimicrobial activity of antimicrobial preservatives and applications thereof in personal care products, cosmetic products and home care products, and, more particularly, to certain ether compounds as such multifunctional boosters. BACKGROUND OF THE INVENTION Protection against microbial contamination of personal care products, cosmetic products, and home care products is of high importance to these product industries. Traditional preservatives, such as isothiazolinones, formaldehyde releasers, parabens, and IPBC, are under increased scrutiny from regulatory agencies and environmental working groups. In many cases, product formulators are seeking solutions to reduce the dosing levels of traditional preservatives without compromising the level of preservation. Many product formulators are also turning to “soft” preservatives, such as phenoxyethanol, alcohols and/or organic acids. Because soft preservatives alone often do not provide robust full-spectrum antimicrobial efficacy, particularly at desired dosing levels, formulators may use them in combination with booster compounds to provide more robust protection to product compositions. Additionally, many product compositions include ingredients which do not directly benefit the target substrate but are necessary to provide rheological or other chemical and/or mechanical properties to the applied product. Many of these ingredients may result in incidental and undesirable effects, including, for example, increases in tackiness or propensity for residue formation and decreases in consumer perception of desirable sensory or manageability attributes. Furthermore, there is an increased demand for product formulations that provide multiple benefits in one product or product application. WO 2014/191258 A2 is directed to antimicrobial compositions comprising certain glyceryl ethers, and WO 2022/128882 A1 is directed to a combination of n-heptyl-glyceryl ether and certain preservative compounds. These references do not disclose the alkenyl ether compounds (e.g., allyl ether compounds) of formula (I) of the present disclosure, the present compounds’ enhancement of the activity of antimicrobial preservatives or their multifunctional properties, as described herein. There is a need to provide booster compounds that enhance the antimicrobial efficacy of antimicrobial preservatives in personal care, cosmetic and home care product compositions, thereby decreasing the number and/or concentration of antimicrobial preservatives otherwise required to achieve sufficient protection. Further, there is a need to provide compounds with multifunctional benefits, such as 1    Docket No.: P243 00001‐WO‐PCT  antioxidant, surfactant, humectant and/or chelating properties, allowing formulators to prepare products with reduced numbers and/or amounts of ingredients without compromising (and potentially even enhancing) the benefit of the end product. These needs are addressed by the present application, which is based on the surprising discovery that the ether compounds of formula (I) disclosed herein act as boosters to enhance the antimicrobial activity of antimicrobial preservatives, thereby allowing for the achievement of broad spectrum antimicrobial efficacy, while reducing the number and/or concentration of antimicrobial preservatives otherwise required to achieve sufficient broad spectrum protection. The present disclosure is further based on the discovered multifunctional nature of the presently disclosed ether compounds, as it was surprisingly found that such compounds exhibit one or more further properties, such as one or more of antioxidant, surfactant, humectant and/or chelating properties, which can be provided to product formulations. SUMMARY OF INVENTION Provided is a personal care, cosmetic or home care product composition comprising an antimicrobial preservative and an ether compound of formula (I) (I),
Figure imgf000003_0001
C6 alkenyl, –R6–OH, or –R8–O–R9; R2 is –C1-C6 alkyl, –C2-C6 alkenyl, –R6–OH, –O–R7, or –R8–O–R9; R3 is –OH, –R6–OH, –O–R7 or –R8–O–R9; R4 is –C2-C5 alkenyl; and R5 is H, –C1-C5 alkyl, or –C2-C5 alkenyl; and, with respect to R1, R2 and R3 independently of one another, R6 is –C1-C6 alkylene or –C3-C6 alkenylene, R7 is –C1-C6 alkyl or –C3-C6 alkenyl, R8 is –C1- C5 alkylene or –C3-C5 alkenylene, and R9 is –C1-C5 alkyl or –C3-C5 alkenyl. Preferably, at least one of R1, R2 or R3 contains a –OH group. In another aspect, a method of providing antimicrobial activity to a personal care, cosmetic or home care product composition (e.g., controlling or inhibiting the growth of microorganisms in a product composition) comprises adding to the composition an antimicrobial preservative and an ether compound of formula (I) as described herein. In a further aspect, the present disclosure provides for the use of an ether compound of formula (I) as described herein for enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition. 2    Docket No.: P243 00001‐WO‐PCT  In another aspect, provided is a method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) as described herein. The antimicrobial efficacy is enhanced as compared to an equal amount of the antimicrobial preservative without the ether compound. In a further aspect, provided is a method of reducing the minimum amount of an antimicrobial preservative needed for preservation activity in a personal care, cosmetic or home care product composition, the method comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) as described herein, wherein after said combination or mixing with the ether compound, the minimum amount of the antimicrobial preservative needed for preservation activity in the product composition is less than if the antimicrobial preservative was used alone. In another aspect, an antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) as described herein. DETAILED DESCRIPTION The ether compounds of the present disclosure are of the formula (I): , alkenyl, –R6–OH, or –R8–O–R9;
Figure imgf000004_0001
R2 is –C1-C6 alkyl, –C2-C6 alkenyl, –R6–OH, –O–R7, or –R8–O–R9; R3 is –OH, –R6–OH, –O–R7 or –R8–O–R9; R4 is –C2-C5 alkenyl (e.g., C2-C3 alkenyl); and R5 is H, –C1-C5 alkyl (e.g., C1-C3 alkyl), or –C2-C5 alkenyl (e.g., C2-C3 alkenyl). With respect to the oxygen-containing groups of R1, R2 and R3 independently of one another, R6 is – C1-C6 alkylene (e.g., –C1-C4 alkylene or –C1-C2 alkylene) or –C3-C6 alkenylene (e.g., –C3-C4 alkenylene), R7 is –C1-C6 alkyl (e.g., –C1-C4 alkyl or –C1-C2 alkyl) or –C3-C6 alkenyl (e.g., –C3-C4 alkenyl), R8 is –C1-C5 alkylene (e.g., –C1-C3 alkylene) or –C3-C5 alkenylene (e.g., –C3 alkenylene), and R9 is –C1-C5 alkyl (e.g., –C1-C3 alkyl) or –C3-C5 alkenyl (e.g., –C3 alkenyl). Preferably, at least one of R1, R2, or R3 contains a –OH group. For example, at least one of R1, R2, or R3 may contain a –OH group, and at least one other of R1, R2, or R3 may contain an ether group. In many preferred embodiments, at least two of R1, R2, or R3 contain a –OH group. In such embodiments, the other of R1, R2, or R3 may, but need not, contain a –OH group or an ether group. In further embodiments, R1, R2, and R3 each contains a –OH group. 3    Docket No.: P243 00001‐WO‐PCT  In other embodiments, at least one of R1, R2, or R3 contains a –OH group, and the remaining two each contains an ether group. It shall be understood that references to R1, R2, and/or R3 containing “a –OH group” or “an ether group,” as applicable, refer to the respective groups described herein from which R1, R2, and R3 are selected that contain the specified functional group (i.e., that contain hydroxyl or ether). For example, where R3 is said to contain a –OH group, this indicates R3 is –OH or –R6–OH. As a further example, where R3 is said to contain an ether group, this indicates R3 is –O–R7 or –R8–O–R9. The same principle applies herein to the extent R1, R2, and/or R3 are said to have an oxygen-containing group or functionality. In general, the total number of carbons in R1, R2, and R3 combined is typically no more than 12, such as no more than 8 or no more than 6. For example, in many embodiments, the total number of carbons in R1, R2, and R3 combined ranges from 1 to 12, such as from 2 to 12, from 3 to 12 or from 4 to 12, often from 1 to 8, from 2 to 8, from 3 to 8, from 4 to 8, from 1 to 6, from 2 to 6, or from 3 to 6. In general, the total number of carbons in R8 and R9 combined is typically no more than 6, or, in many embodiments, no more than 4. More than one ether compound of formula (I) may be present or used in the compositions and methods of the present disclosure. Preferably, R1 in formula (I) is H, –C1-C4 alkyl, –C2-C4 alkenyl, –R6–OH, or –R8–O–R9, where R6, R8, and R9 are as described herein. For example, in many embodiments, R1 is H, –C1-C4 alkyl, –C2-C4 alkenyl or –R6–OH, often H, –R6–OH or –C1-C4 alkyl (e.g., methyl or ethyl). In many further embodiments, R1 is –R6–OH or –R8–O–R9, preferably –R6–OH, where R6, R8, and R9 are as described herein. Preferably, R2 in formula (I) is –C1-C4 alkyl, –C2-C4 alkenyl, –R6–OH, –O–R7, or –R8–O–R9, where R6-R9 are as described herein. For example, in many embodiments, R2 is –C1-C4 alkyl (e.g., –C1-C2 alkyl) or –C2-C4 alkenyl. In many other embodiments, R2 is R6–OH, –O–R7, or –R8–O–R9, preferably R6–OH, where R6-R9 are as described herein. R3 in formula (I) is –OH, –R6–OH, –O–R7 or –R8–O–R9, where R6-R9 are as described herein. Preferably, R2 and R3 are each independently selected to have an oxygen-containing functionality as described herein. That is, R2 is –R6–OH, –O–R7, or –R8–O–R9, and R3 is –OH, –R6–OH, –O–R7 or – R8–O–R9, where R6-R9 are as described herein. R2 and R3 may, but need not, be the same. Preferably, R2 is –R6–OH and R3 is –OH or –R6–OH. In other embodiments, at least one of R2 or R3 contains a –OH group and the other contains an ether group. For example, R2 may be –R6–OH and R3 may be –O–R7 or –R8–O–R9. In other embodiments, R2 and R3 are each independently –O–R7 or –R8–O–R9, preferably where R1 is –R6–OH. 4    Docket No.: P243 00001‐WO‐PCT  It should be understood that in embodiments where R2 and R3 are each –R6–OH, are each –O–R7, or are each–R8–O–R9, the R6-R9 groups as applicable may, but need not, be the same in each of R2 and R3 (the same applies with respect to the R6, R8 and R9 groups of R1 in relation to R2 and R3). For example, in many preferred embodiments, R2 and R3 are each independently –R6–OH, where R6 for R2 may be different or the same as R6 for R3, such as where R6 in each is the same or different –C1-C6 alkylene or –C1-C4 alkylene (e.g., chosen from methylene and ethylene). In another example, in many embodiments, R2 and R3 are each independently –R8–O–R9, where R8 and R9 for R2 may be different or the same as for R3 (e.g., where R8 in each is the same or different –C1-C5 alkylene or –C1-C3 alkylene (e.g., chosen from methylene and ethylene) and R9 in each is the same or different –C3-C5 alkenyl (e.g., –C3 alkenyl). In further embodiments, R2 is –O–R7 or –R8–O–R9, preferably –R8–O–R9, and R3 is –OH or –R6–OH, such as where R2 is –R8–O–R9, and R3 is –R6–OH (and, for example, where R6 and R8 are each independently alkylene as described herein, and R9 is alkenyl as described herein). In further embodiments, for example, R2 is alkyl or alkenyl as described herein, and R3 is– OH, –R6–OH, –O–R7, or –R8–O–R9. As mentioned above, preferably at least one of R1, R2, or R3 contains a –OH group, and thus R1 is preferably –R6–OH in embodiments where neither R2 nor R3 contains a –OH group. It should be understood that the selections for R1 as described herein may be chosen with any combination of R2 and R3 as described herein, preferably wherein at least one of R1, R2, or R3 contains a –OH group. The same applies to the selections for R2 relative to R1 and R3 and to the selections for R3 relative to R1 and R2, preferably, in each case, wherein at least one of R1, R2, or R3 contains a –OH group. For example, in many embodiments, any combination of R2 and R3 is selected, preferably wherein at least one of R2 or R3 contains a –OH group (e.g., R2 is alkyl, alkenyl or –R6–OH as described herein and R3 is –OH or –R6–OH), and R1 is H, –R6–OH, alkyl or alkenyl as described herein, often H, –R6–OH or –C1-C6 alkyl or –C1-C4 alkyl (e.g., methyl or ethyl). In further embodiments, any combination of R2 and R3 is selected where R2 and R3 each independently has an oxygen-containing functionality, preferably wherein at least one (or both) of R2 or R3 contains a –OH group, and R1 is H, –R6–OH, alkyl or alkenyl as described herein, often H, –R6–OH or –C1-C6 alkyl or –C1-C4 alkyl (e.g., methyl or ethyl). R1, R2 and R3 in formula (I) each may be independently selected to have an oxygen-containing functionality as described herein, preferably wherein at least one of R1, R2, or R3 contains a –OH group. That is, R1 is –R6–OH or –R8–O–R9, R2 is –R6–OH, –O–R7, or –R8–O–R9, and R3 is –OH, – R6–OH, –O–R7 or –R8–O–R9, where R6-R9 are as described herein, preferably wherein at least one of R1, R2, or R3 contains a –OH group. For example, R1 and R2 may each independently be –R6–OH, and R3 may be –OH or –R6–OH. As described above, R6 in R1, R2 and R3 may be the same or different, such as where R6 is the same or different –C1-C6 alkylene or –C1-C4 alkylene (e.g., chosen from methylene and ethylene). 5    Docket No.: P243 00001‐WO‐PCT  R4 in formula (I) contains a non-aromatic carbon–carbon double bond. More specifically, R4 is –C2- C5 alkenyl. Preferably, any combination of R1, R2, and R3 as described herein is selected, and R4 is C2-C3 alkenyl, preferably C2 alkenyl. R5 in formula (I) is H, –C1-C5 alkyl (e.g., C1-C3 alkyl), or –C2-C5 alkenyl (e.g., C2-C3 alkenyl). Preferably, any combination of R1 to R4 as described herein is selected, and R5 is H, particularly, for example, where R4 is C2 alkenyl, meaning R4, R5 and the carbon atom to which they are each attached collectively form an allyl group. In these preferred embodiments, the ether compounds of formula (I) are said to be allyl ether compounds. In other embodiments, R5 is a short chain alkyl or alkenyl as described herein. “Alkyl,” “alkylene,” “alkenyl,” and “alkenylene” groups as used herein may be unbranched or branched depending upon the selected chain length. Examples of ether compounds of the formula (I) include, without limitation, 2-(allyloxymethyl)-2- ethyl-1,3-propanediol (i.e., trimethylolpropane allyl ether), 2,2-bis(allyloxymethyl)-2- ethylpropanediol (i.e., trimethylolpropane diallyl ether), 3-allyloxy-1,2-propanediol and 2,2- bis(hydroxymethyl)-1,3-propanediol allyl ether (i.e., pentaerythritol allyl ether). The ether compound of formula (I) may be synthesized according to known methods or may be obtained as a commercially available compound. In a further aspect of the present disclosure, the ether compounds as described herein have one or more properties chosen from antioxidant, surfactant, humectant and chelating properties, such as described or demonstrated herein. Preferably, at least two of R1, R2, or R3 contain a –OH group, and the ether compound has at least a chelating property. Preferably, at least two of R1, R2, or R3 contain a –OH group, and the ether compound has at least an antioxidant property. More preferably, at least two of R1, R2, or R3 contain a –OH group, and the ether compound has at least an antioxidant property and a chelating property, or at least an antioxidant property, a chelating property and a surfactant property, or at least an antioxidant property, a chelating property, a surfactant property and a humectant property. For example, in such embodiments, R2 may be –R6–OH, R3 may be –OH or – R6–OH, and R1 may be as described herein, preferably where R1 is H, –R6–OH, alkyl or alkenyl as described herein, often H, –R6–OH or –C1-C6 alkyl or –C1-C4 alkyl (e.g., methyl or ethyl). Preferably, as the above-referenced antioxidant property, the ether compound of formula (I) shows a μM Trolox equivalents (TE) value (i.e., μmol Trolox/L sample) of at least 25 μM TE, more preferably at least 50 μM TE or at least 75 μM TE, in particular at least 100 μM TE, at least 125 μM TE or at least 150 μM TE, where the TE value is determined according to the assay procedure of the Activated ABTS Antioxidant Assay Kit (Cat# AOX-14) (instruction manual ZBM0123.00, April 2021). Preferably, as the above-referenced chelating property, the ether compound of formula (I) shows a μM EDTA equivalents value (i.e., µmol EDTA/L sample) of at least 50 μM EDTA equivalents, more preferably 6    Docket No.: P243 00001‐WO‐PCT  at least 75 μM EDTA equivalents or at least 100 μM EDTA equivalents, in particular at least 150 μM EDTA equivalents, at least 175 μM EDTA equivalents or at least 200 μM EDTA equivalents, where the EDTA equivalents value is determined according to the assay procedure of the Cupric Ion Chelating Assay Kit (Cat# AOX-16) (instruction manual ZBM0125.00, July 2021). As the antimicrobial preservative, traditional and/or soft preservatives may be used. The ether compounds of formula (I) can be used to decrease the number and/or amount of such antimicrobial preservatives otherwise required to achieve desired preservation activity in personal care products, cosmetics products and home care products. Suitable antimicrobial preservatives for personal care products, cosmetic products, and home care products are known in the art. Examples of such traditional preservatives include isothiazolinones (e.g., 5-chloro-2-methyl-4-isothiazolin-3-one (CMIT), 2-methyl-4-isothiazolin-3-one (MIT), and 1,2-benzisothiazolin-3-one (BIT)), formaldehyde releasers (e.g., bronopol and 1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione), and parabens (e.g., methylparaben, ethylparaben, propylparaben, and butylparaben). The antimicrobial preservative may be a soft preservative. Preferably, the antimicrobial preservative comprises an isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), an alkylhydroxamic acid and/or salt thereof (e.g., hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid, salts thereof, combinations thereof, preferably caprylhydroxamic acid and/or a salt thereof), an aromatic aldehyde (e.g., cinnamic aldehyde), an alcohol (e.g., an aromatic alcohol, such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic alcohol, a phenolic compound, such as hydroxyacetophenone, combinations thereof), a diol (e.g., bronopol, glycols, such as 1,2-propanediol, 1,3-butanediol, 1,2- pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., caprylyl glycol), combinations thereof), a glyceryl ether (e.g., ethylhexylglycerin, chlorphenesin), an aromatic ether (e.g., phenoxyethanol), a pyrithione (e.g., zinc pyrithione, sodium pyrithione), an organic acid (e.g., benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4- hydroxybenzoic acid, combinations thereof), a salt and/or ester of an organic acid (e.g., esters and/or salts of the above organic acids, such as salts of sodium, potassium, calcium, magnesium or ammonium, including, e.g., sodium benzoate, potassium sorbate and the like, and esters of methyl, ethyl, propyl, isopropyl, butyl, isobutyl or phenyl, including butyl benzoate and the like), ethyl lauroyl arginate (LAE), or any combination of the foregoing. For example, the antimicrobial preservative may comprise an alkylhydroxamic acid and/or salt thereof (preferably, hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid and/or salt thereof or combination thereof, particularly caprylhydroxamic acid and/or salt thereof), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, 1,2- pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., caprylyl glycol), bronopol, 7    Docket No.: P243 00001‐WO‐PCT  ethylhexylglycerin, chlorphenesin, CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, a salt and/or ester of the foregoing acids, zinc pyrithione, sodium pyrithione or a combination thereof. Preferably, the antimicrobial preservative comprises an isothiazolinone, an aromatic aldehyde, an aromatic alcohol, an aromatic ether, an organic acid, a salt or ester of an organic acid, a pyrithione, ethyl lauroyl arginate (LAE) or a combination thereof. In particular, the antimicrobial preservative may comprise caprylhydroxamic acid, phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenethyl alcohol, ethyl lauroyl arginate (LAE), CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4- dienoic acid, 4-hydroxybenzoic acid, an ester or salt of said organic acids (e.g., sodium benzoate, potassium sorbate and the like), or a combination thereof. For example, the antimicrobial preservative may comprise phenoxyethanol, benzyl alcohol, benzoic acid, a salt of benzoic acid (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT or a combination thereof. More than one antimicrobial preservative may be present or used in the compositions and methods of the present disclosure. Optimized amounts of the ether compound of the present application and the antimicrobial preservative may vary depending, for example, on the particular compound and preservative selected, the end use application, the desired level of preservation, the final properties of the product, and the like. In general, the ether compound is present in an amount effective to enhance the antimicrobial efficacy (e.g., enhance a desired preservative, antibacterial and/or antifungal effect) of the antimicrobial preservative in a product composition, such as a personal care, cosmetic or home care composition, (e.g., to meet or even exceed industry standards for antimicrobial efficacy) as compared to an equal amount of the antimicrobial preservative without the ether compound. In addition, the amount of the ether compound may also be influenced by the desired multifunctional benefits, such as one or more of antioxidant, surfactant, humectant and/or chelating properties, as described herein. For example, preferably, in the formula (I), at least two of R1, R2, or R3 contain a –OH group (e.g., R2 is –R6–OH, R3 is –OH or –R6–OH, and R1 is as described herein, preferably where R1 is H, –R6–OH, alkyl or alkenyl as described herein, often H, –R6–OH or –C1-C6 alkyl or –C1-C4 alkyl (e.g., methyl or ethyl)), and the amount of the ether compound in the product composition provides at least a chelating property to the product composition. Preferably, at least two of R1, R2, or R3 contain a –OH group (e.g., R2 is –R6–OH, R3 is –OH or –R6–OH, and R1 is as described herein, preferably where R1 is H, – R6–OH, alkyl or alkenyl as described herein, often H, –R6–OH or –C1-C6 alkyl or –C1-C4 alkyl (e.g., methyl or ethyl)), and the amount of the ether compound provides at least an antioxidant property to the product composition. More preferably, at least two of R1, R2, or R3 contain a –OH group (e.g., R2 is –R6–OH, R3 is –OH or –R6–OH, and R1 is as described herein, preferably where R1 is H, –R6–OH, 8    Docket No.: P243 00001‐WO‐PCT  alkyl or alkenyl as described herein, often H, –R6–OH or –C1-C6 alkyl or –C1-C4 alkyl (e.g., methyl or ethyl)), and the amount of the ether compound provides at least an antioxidant property and a chelating property to the product composition, or at least an antioxidant property, a chelating property and a surfactant property to the production composition, or at least an antioxidant property, a chelating property, a surfactant property and a humectant property to the product composition. Preferably, as the above-referenced antioxidant property provided to the product composition, an amount of the ether compound of formula (I), such as an exemplary amount disclosed herein (e.g., from about 0.01 wt%, from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 5 wt%, preferably to about 3 wt%, to about 2 wt%, more preferably to about 1.5 wt%, or to about 1 wt%, based on the weight of the composition) may be used in the product composition to increase the μM Trolox equivalents value of the composition (i.e., μmol Trolox/L sample) by at least 10%, more preferably by at least 15%, by at least 20% or by at least 25%, in particular by at least 30%, by at least 40% or by at least 50%, compared to the μM Trolox equivalents value of the composition in the absence of the ether compound of formula (I), where the μM Trolox equivalents value is determined according to the assay procedure of the Activated ABTS Antioxidant Assay Kit (Cat# AOX-14) (instruction manual ZBM0123.00, April 2021). Preferably, as the above-referenced chelating property provided to the product composition, an amount of the ether compound of formula (I), such as an exemplary amount disclosed herein (e.g., from about 0.01 wt%, from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 5 wt%, preferably to about 3 wt%, to about 2 wt%, more preferably to about 1.5 wt%, or to about 1 wt%, based on the weight of the composition) may be used in the product composition to increase the μM EDTA equivalents value of the composition (i.e., µmol EDTA/L sample) by at least 10%, more preferably by at least 15%, by at least 20% or by at least 25%, in particular by at least 30%, by at least 40% or by at least 50%, compared to the μM EDTA equivalents value of the composition in the absence of the ether compound of formula (I), where the μM EDTA equivalents value is determined according to the assay procedure of the Cupric Ion Chelating Assay Kit (Cat# AOX-16) (instruction manual ZBM0125.00, July 2021). In general, the weight ratio of the ether compound to the antimicrobial preservative may range from about 1:50 to about 50:1, such as from about 1:20 to about 20:1, from about 1:15 to about 15:1, from about 1:10 to about 10:1, or from about 1:5 to about 5:1, although other ratios may be used. The present application provides for the use of the presently disclosed ether compounds and antimicrobial preservatives in product compositions, such as personal care products, cosmetic products and home care products. In general, the ether compound and the antimicrobial preservative each may be present in the product composition in an amount ranging from about 0.001 wt%, from about 0.005 wt%, preferably from about 0.01 wt%, from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 5 wt%, preferably to about 3 wt%, to about 2 wt%, 9    Docket No.: P243 00001‐WO‐PCT  more preferably to about 1.5 wt%, or to about 1 wt%, based on the weight of the product composition, according to any combination of the foregoing lower and upper boundaries and any range therebetween. Depending upon the antimicrobial preservative, even lower amounts of the antimicrobial preservative may be used, such as from about 0.0001 wt% or higher or from about 0.0005 wt% or higher. In certain of such embodiments, the antimicrobial preservative is an isothiazolinone, preferably CMIT, MIT, BIT or a combination thereof. In embodiments where such small amounts of the antimicrobial preservative is used, the amount by weight of the ether compound may be substantially proportionally higher than the amount by weight of the antimicrobial preservative, such as a ratio of the ether compound to the antimicrobial preservative as high as 100:1, as high as 500:1, as high as 1000:1, as high as 5000:1, or higher. In certain of such embodiments, the antimicrobial preservative is an isothiazolinone, preferably CMIT, MIT, BIT or a combination thereof. Typically, the combined amount of the ether compound and antimicrobial preservative ranges from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 10 wt%, preferably to about 5 wt%, more preferably to about 3 wt%, to about 2 wt%, to about 1.5 wt% or to about 1 wt%, based on the weight of the product composition, according to any combination of the foregoing lower and upper boundaries and any range therebetween. For example, the combined amount may be from about 0.05 to about 7 wt%, such as from about 0.1 to about 5 wt%, from about 0.1 to about 4 wt%, from about 0.1 to about 3 wt%, or from about 0.1, from about 0.3 or from about 0.5 to about 3, to about 2 or to about 1 wt%, based on the weight of the product composition. Typically, the ether compound and the antimicrobial preservative each is present in the product composition in an amount not exceeding about 2 wt%, preferably not exceeding about 1.5 wt% or not exceeding about 1 wt%, based on the weight of the product composition. Often each is present below 1 wt%. Preferably, the combined amount of the ether compound and antimicrobial preservative does not exceed about 3 wt% or does not exceed about 2 wt%, such as ranging from about 1.5 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.5 wt%), from about 1.2 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.2 wt%) or from about 1 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1 wt%), based on the weight of the product composition. The ether compound may be combined with the antimicrobial preservative or added to a product composition in any suitable manner. The ether compound may be added to a product composition prior to the addition of the antimicrobial preservative, concurrently with the addition of the antimicrobial preservative or after the addition of the antimicrobial preservative. 10    Docket No.: P243 00001‐WO‐PCT  The ether compounds of the present disclosure can be incorporated into any number and variety of different personal care, cosmetic and home care products, particularly aqueous-based formulations, both water soluble or using water as a carrier, including emulsions (whether oil-in-water or water-in- oil). Examples include, without limitation, household products and cleaners, fabric detergents, dish detergents, cleansers, soaps, bubble baths, disinfectants, deodorizers, hygiene compositions, infant care products, antimicrobial soaps, hand sanitizers, deodorants, antiperspirants, dermatological compositions, skin conditioners, skin moisturizers, anti-wrinkle formulations, sunscreens, tanning lotions, hair products, shampoos, shower gels, conditioners, shaving creams, etc. Personal care products include, for example, products used in skincare, hair care, oral care, personal cleaning or hygiene, sun protection and other applications. Examples of personal care products include shampoos, conditioners, shower gels, liquid soaps, skin lotions, and liquids for any personal care wet wipe application. Examples of cosmetic products include face creams, makeup, makeup removers, mascaras and wet wipes. Examples of home care products include dish soaps, laundry detergents, cleaning wipes and cleaning formulations. The product compositions may contain numerous and different ingredients depending on the end use application, that is, one or more additional ingredients suitable for use in a personal care, cosmetic or home care product composition. In one example, a personal care composition comprises an antimicrobial preservative and an ether compound of formula (I), as described herein, and one or more additional ingredients suitable for use in a personal care composition. In another example, a cosmetic composition comprises an antimicrobial preservative and an ether compound of formula (I), as described herein, and one or more additional ingredients suitable for use in a cosmetic composition. The personal care or cosmetic composition may be, for example, any formulation for skin care, hair care, cosmetics, personal cleaning, hygiene, sun protection and other similar applications. Examples of such products include, without limitation, skin toners, skin cleansers, night creams, skin creams, shaving creams, skin lotions, makeup, mascara, lipstick, blush, gloss, eye-liner, makeup removers, sunscreens, lip balms, fragrances, massage oils, shampoos, conditioners, hair styling gels, hair reparatives, hair tonics, hair fixatives, hair mousses, bath and shower gels, liquid soaps, moisturizing sprays, bath additives, ophthalmic preparations, foaming soaps and body washes, liquids for any personal care wet wipe application, etc. Depending on the application, the personal care or cosmetic composition may contain numerous and different compatible ingredients, such as any of solvents, surfactants, emulsifiers, rheology modifiers, conditioners, emollients, skin care ingredients, moisturizers, thickeners, humectants, fillers, antioxidants, active ingredients, such as dermatologically active ingredients typically suited for topical application, fragrances and the like, and various mixtures thereof. As another example, a home care composition comprises an antimicrobial preservative and an ether compound of formula (I), as described herein, and one or more additional ingredients suitable for use 11    Docket No.: P243 00001‐WO‐PCT  in a home care composition. Examples include dish soaps, laundry detergents, cleaning wipes, cleaning formulations and other home care applications. Depending on the application, the home care composition may contain, for example, detergents, emulsifiers, surfactants, thickeners, gelling agents, bleaches, whiteners, deodorizers, enzymes, stabilizers, fragrances and the like, and various mixtures thereof. Examples of the foregoing ingredients and other agents used in personal care, cosmetic and home care product compositions are known in the art. The ether compounds of the present disclosure may be included in product compositions of a variety of different forms, for example, liquids, pastes, serums, hydrogels, creams, emulsions, lotions, gels, oils, wipes, ointments, semi-solid compositions, and aerosol sprays. For example, they can be used in hair care products, such as shampoos, hair conditioners, hair dyes, hair tonic, hair gel, hair dressings, hair grooming aids and other hair care preparations; shaving applications such as shaving cream, aftershave lotions, and other shaving applications; personal cleaners for the body and hands, such as liquid bath soaps and detergents; fragrance preparations, such as perfumes, after bath splashes, and other similar fragrant preparations, skin care products, such as moisturizers, creams, and lotions and other similar skin care products, make-up products, such as mascara, base foundations and the like; make-up removal products, sun care products, indoor tanning products and other similar personal care products; in formulations used to saturate wipes used for personal cleaning and hygiene, for example, baby wipes, wet toilet wipes, make-up removal wipes and exfoliating wipes the like, or wet wipe formulations for home care. Typically, the product composition has a pH ranging from about 3.0, from about 4.0, from about 5.0, from about 5.5, or from about 6.0 to about 11, such as from about 3.0 to about 10, from about 4.0 to about 8.5, or from about 5.0 to about 7.5. Unless otherwise specified, pH values or ranges refer to pH at room temperature (20-25 °C). The selected pH will vary depending, for example, on the particular end use application. For example, the personal care or cosmetic composition preferably has a pH ranging from about 3.0 or from about 4.0 to about 8.0, such as from about 4.0 or from about 5.0 to about 7.5 or to about 7.0. The home care composition preferably has a pH ranging from about 3.0 to about 11, such as from about 4.0 or from about 5.0 to about 10, or from about 5.0 or from about 6.0 to about 9.0, to about 8.0, to about 7.5 or to about 7.0. In another aspect of the present disclosure, a method of providing antimicrobial activity to a personal care, cosmetic or home care product composition comprises adding to the composition an antimicrobial preservative and an ether compound of formula (I). The present disclosure is not limited to any particular technique for preparing a product composition, and the antimicrobial preservative and the ether compound of formula (I) may be added to a product composition in any suitable manner. For example, the antimicrobial preservative and the ether 12    Docket No.: P243 00001‐WO‐PCT  compound of formula (I) can be applied to a product formulation as a mixture or applied individually to the formulation at the same time or in any order. In a further aspect, the present disclosure provides for the use of an ether compound of formula (I) as described herein for enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition. In another aspect, provided is a method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) as described herein. The antimicrobial efficacy is enhanced as compared to an equal amount of the antimicrobial preservative without the ether compound. In a further aspect, provided is a method of reducing the minimum amount of an antimicrobial preservative needed for preservation activity in a personal care, cosmetic or home care product composition, the method comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) as described herein, wherein after said combining or mixing with the ether compound, the minimum amount of the antimicrobial preservative needed for preservation activity in the product composition is less than if the antimicrobial preservative was used alone. It shall be understood that the descriptions herein with respect to the ether compound of formula (I), the antimicrobial preservative, exemplary ratios and amounts, product compositions and ingredients, etc. also apply to the methods of the present disclosure. Various different microorganisms may be controlled in accordance with the present disclosure. For example, a combination of an antimicrobial preservative and the ether compound of the present disclosure preferably controls gram positive bacteria, gram negative bacteria, and fungi, among other microorganisms. Non-limiting examples include Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa, Escherichia coli, Enterobacter gergoviae, Klebsiella pneumoniae, Burholderia cepacia, Pseudomonas putida, Candida albicans, Aspergillus brasiliensis, and mixtures thereof. As known in the art, an antimicrobial effect may be demonstrated by various suitable antimicrobial effectiveness tests. Preferably, when added to a product composition, the antimicrobial preservative and the ether compound of formula (I) provide an antimicrobial effect according to the challenge test procedures in the below Examples achieving a passing growth rating according to the criteria associated with Table 7 and the associated description herein. In a further aspect of the present disclosure, an antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) as described herein, preferably wherein the antimicrobial preservative and the ether compound of formula (I) collectively constitute from 50 to 100 wt% of the active ingredients in the antimicrobial composition, further preferably wherein the antimicrobial preservative comprises an isothiazolinone (e.g., CMIT, MIT, BIT, combinations 13    Docket No.: P243 00001‐WO‐PCT  thereof), an alkylhydroxamic acid and/or salt thereof (e.g., hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid, salts thereof, combinations thereof, preferably caprylhydroxamic acid and/or a salt thereof), an aromatic aldehyde (e.g., cinnamic aldehyde), an alcohol (e.g., an aromatic alcohol, such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic alcohol, a phenolic compound, such as hydroxyacetophenone, combinations thereof), a diol (e.g., bronopol, glycols, such as 1,2-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2- heptanediol, 1,2-octanediol (i.e., caprylyl glycol), combinations thereof), a glyceryl ether (e.g., ethylhexylglycerin, chlorphenesin), an aromatic ether (e.g., phenoxyethanol), a pyrithione (e.g., zinc pyrithione, sodium pyrithione), an organic acid (e.g., benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, combinations thereof), a salt and/or ester of an organic acid (e.g., esters and/or salts of the above organic acids, such as salts of sodium, potassium, calcium, magnesium or ammonium, including, e.g., sodium benzoate, potassium sorbate and the like, and esters of methyl, ethyl, propyl, isopropyl, butyl, isobutyl or phenyl, including butyl benzoate and the like), ethyl lauroyl arginate (LAE), or a combination thereof. For example, the antimicrobial preservative may comprise an alkylhydroxamic acid and/or salt thereof (preferably, hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid and/or salt thereof or combination thereof, particularly caprylhydroxamic acid and/or salt thereof), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, 1,2- pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., caprylyl glycol), bronopol, ethylhexylglycerin, chlorphenesin, CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, a salt and/or ester of the foregoing acids, zinc pyrithione, sodium pyrithione or a combination thereof. Preferably, the antimicrobial preservative comprises an isothiazolinone, an aromatic aldehyde, an aromatic alcohol, an aromatic ether, an organic acid, a salt or ester of an organic acid, a pyrithione, ethyl lauroyl arginate (LAE) or a combination thereof. In particular, the antimicrobial preservative may comprise caprylhydroxamic acid, phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenethyl alcohol, ethyl lauroyl arginate (LAE), CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4- dienoic acid, 4-hydroxybenzoic acid, an ester or salt of said organic acids (e.g., sodium benzoate, potassium sorbate and the like), or a combination thereof. For example, the antimicrobial preservative may comprise phenoxyethanol, benzyl alcohol, benzoic acid, a salt of benzoic acid (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT or a combination thereof. Typically, the antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) in a combined amount that is a majority (>50 wt%) of the active ingredients 14    Docket No.: P243 00001‐WO‐PCT  in the antimicrobial composition, such as at least 60 wt% or at least 70 wt%, preferably at least 80 wt%, more preferably at least 85 wt%, at least 90 wt%, at least 95 wt%, at least 96 wt%, at least 97 wt%, at least 98 wt% or at least 99 wt%, based on the total weight of active ingredients in the antimicrobial composition. The antimicrobial composition often contains from about 60 to 100 wt%, preferably from about 65 to 100 wt%, from about 70 to 100 wt%, from about 75 to 100 wt%, from about 80 to 100 wt%, from about 85 to 100 wt%, from about 90 to 100 wt%, or from about 95 or from about 97 to 100 wt%, of an antimicrobial preservative and an ether compound of formula (I) combined, based on the total weight of active ingredients in the antimicrobial composition. In many embodiments, the antimicrobial composition comprises active ingredients consisting essentially of, or in further embodiments consists of, an antimicrobial preservative and an ether compound of formula (I). Preferably, the antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) in a combined amount of 50 to 100 wt% of the total weight of the antimicrobial composition, typically a majority (>50 wt%) of the antimicrobial composition, such as at least 60 wt% or at least 70 wt%, preferably at least 80 wt%, more preferably at least 85 wt%, at least 90 wt%, at least 95 wt%, at least 96 wt%, at least 97 wt%, at least 98 wt% or at least 99 wt%, based on the total weight of the antimicrobial composition. The antimicrobial composition often contains from about 60 to 100 wt%, preferably from about 70 to 100 wt%, from about 75 to 100 wt%, from about 80 to 100 wt%, from about 85 to 100 wt%, from about 90 to 100 wt%, or from about 95 or about 97 to 100 wt%, of an antimicrobial preservative and an ether compound of formula (I) combined, based on the total weight of the antimicrobial composition. In many embodiments, the antimicrobial composition consists essentially of, or in further embodiments consists of, an antimicrobial preservative and an ether compound of formula (I). The antimicrobial composition may, but need not, comprise one or more added solvents or carriers. If present, the solvent or carrier typically constitutes from about 10 wt%, from about 20 wt% or from about 30 wt% to about 90 wt%, to about 85 wt%, to about 80 wt%, to about 70 wt%, to about 60 wt% or to about 50 wt%, based on the total weight of the antimicrobial composition. Solvents or carriers may be chosen according to their compatibility or suitability for a desired end application or end product formulation, such as in a personal care, cosmetic or home care composition, (e.g., a cosmetically acceptable solvent or carrier). Suitable solvents and carriers include, but are not limited to, water, water-miscible solvents, C1-C4 alcohols, C1-C4 diols (e.g., glycols), glycerin and the like. The antimicrobial composition may, but need not, contain one or more excipients, typically in minor quantities. Excipients may similarly be chosen according to their compatibility or suitability for a desired end application or end product formulation, such as in a personal care, cosmetic or home care composition, (e.g., a cosmetically acceptable excipient). Examples of excipients include, but are not 15    Docket No.: P243 00001‐WO‐PCT  limited to, a dispersant, solubilizer, buffer, and/or stabilizer. The antimicrobial composition may comprise, for example, from 0 to about 10 wt% of one or more excipients, such as from about 0.001 wt%, from about 0.01 wt%, from about 0.05 wt% or from about 0.1 wt% to about 5 wt%, to about 3 wt%, or to about 1 wt%, based on the total weight of the antimicrobial composition. For example, the amount of excipients may range from 0 to about 5 wt%, from 0 to about 3 wt% from about 0.01 to about 5 wt%, from about 0.1 to about 5 wt%, from about 0.01 to about 3 wt%, from about 0.1 to about 3 wt%, from about 0.01 to about 1 wt%, or from about 0.1 to about 1 wt%. In general, the antimicrobial composition may comprise a combined amount of an antimicrobial preservative and an ether compound of formula (I) of from about 10 to 100 wt%, such as from about 15 wt% or from about 20 wt%, from about 30 wt%, from about 40 wt%, from about 50 wt% or from about 60 wt% to 100 wt%, to about 99 wt%, to about 97 wt%, to about 95 wt%, to about 90 wt%, to about 80 wt%, or to about 70 wt%, based on the total weight of the antimicrobial composition; optionally one or more solvents or carriers in an amount from 0 to about 90 wt%, such as from about 10 wt%, from about 20 wt% or from about 30 wt% to about 90 wt%, to about 85 wt%, to about 80 wt%, to about 70 wt%, to about 60 wt%, to about 50 wt%, or to about 40 wt%, based on the total weight of the antimicrobial composition; and optionally one or more excipients in an amount from about 0 to about 10 wt%, such as from about 0.001 wt%, from about 0.01 wt%, from about 0.05 wt% or from about 0.1 wt% to about 5 wt%, to about 3 wt%, or to about 1 wt%, based on the total weight of the antimicrobial composition. For example, the combined amount of an antimicrobial preservative and an ether compound of formula (I) may be from about 10 wt% to about 90 wt%, from about 20 wt% to about 80 wt%, or from about 30 wt% to about 70 wt%, and the amount of solvent or carrier may be from about 10 wt% to about 90 wt%, from about 20 wt% to about 80 wt%, or from about 30 wt% to about 70 wt%, optionally further comprising one or more excipients. In many embodiments, the antimicrobial composition consists essentially of, or in further embodiments consists of, an antimicrobial preservative, an ether compound of formula (I), optionally one or more solvents or carriers and optionally one or more excipients. The antimicrobial composition can be added to a product composition in an amount effective to achieve a desired level of antimicrobial efficacy in or preservation of the product composition. It shall be understood that the descriptions herein with respect to the ether compound of formula (I), the antimicrobial preservative, exemplary ratios and amounts, product compositions and ingredients, etc. also apply to the antimicrobial composition of the present disclosure and/or its addition to product compositions, particularly personal care, cosmetic or home care product compositions. The present disclosure further includes, without limitation, the following exemplary embodiments. 16    Docket No.: P243 00001‐WO‐PCT  Embodiment 1: An antimicrobial composition comprising an antimicrobial preservative and an ether compound of formula (I) ,
Figure imgf000018_0001
alkenyl, –R6–OH, or –R8–O–R9; R2 is –C1-C6 alkyl, –C2-C6 alkenyl, –R6–OH, –O–R7, or –R8–O–R9; R3 is –OH, –R6–OH, –O–R7 or –R8–O–R9; R4 is –C2-C5 alkenyl; and R5 is H, –C1-C5 alkyl, or –C2-C5 alkenyl; and, with respect to R1, R2 and R3 independently of one another, R6 is –C1-C6 alkylene or –C3-C6 alkenylene, R7 is –C1-C6 alkyl or –C3-C6 alkenyl, R8 is –C1-C5 alkylene or –C3-C5 alkenylene, and R9 is –C1-C5 alkyl or –C3-C5 alkenyl. Embodiment 2: A product composition comprising the ether compound of formula (I) as described in Embodiment 1 and an antimicrobial preservative, wherein the product composition is chosen from personal care products, cosmetic products, and home care products. Embodiment 3: A method of providing antimicrobial activity to a product composition, comprising adding to the product composition an antimicrobial preservative and the ether compound of formula (I) as described in Embodiment 1, and the product composition is chosen from personal care products, cosmetic products, and home care products. Embodiment 4: A method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, comprising adding to the product composition the ether compound of formula (I) as described in Embodiment 1, wherein the product composition is chosen from personal care products, cosmetic products, and home care products. Embodiment 5: A method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, comprising combining or mixing the antimicrobial preservative with an ether compound as described in Embodiment 1, wherein the product composition is chosen from personal care products, cosmetic products, and home care products. Embodiment 6: Use of the ether compound of formula (I) as described in Embodiment 1 for enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, wherein the product composition is chosen from personal care products, cosmetic products, and home care products. 17    Docket No.: P243 00001‐WO‐PCT  Embodiment 7: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-6, wherein at least one of R1, R2 or R3 contains a –OH group. Embodiment 8: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-7, wherein at least one of R1, R2 or R3 contains a –OH group, and at least one other of R1, R2 or R3 contains an ether group. Embodiment 9: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-8, wherein at least two of R1, R2, or R3 contain a –OH group. Embodiment 10: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-7, wherein R1, R2, and R3 each contains a –OH group. Embodiment 11: The antimicrobial composition, product composition, method or use according to one of Embodiments 1-10, wherein the total number of carbons in R1, R2, and R3 combined is no more than 12, preferably no more than 8 or no more than 6. Embodiment 12: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-11, wherein R1 in formula (I) is H, –R6–OH, –R8–O–R9, –C1-C4 alkyl or – C2-C4 alkenyl; or R1 is H, –R6–OH, –C1-C4 alkyl or –C2-C4 alkenyl; or R1 is H, –R6–OH or –C1-C4 alkyl; or R1 is H, –C1-C4 alkyl or –C2-C4 alkenyl. Embodiment 13: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-9, 11 and 12, wherein R2 in formula (I) is –C1-C4 alkyl or –C2-C4 alkenyl. Embodiment 14: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-12, wherein R2 in formula (I) is R6–OH, –O–R7, or –R8–O–R9. Embodiment 15: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-12 and 14, wherein R2 is R6–OH, and R3 is –OH or –R6–OH. Embodiment 16: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-9, 11, 12, and 14, wherein R2 is O–R7 or –R8–O–R9, and R3 is –OH or – R6–OH, preferably wherein R2 is –R8–O–R9, and further preferably wherein R1 is H, –R6–OH, –C1-C4 alkyl or –C2-C4 alkenyl or R1 is H, –R6–OH or –C1-C4 alkyl. Embodiment 17: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-16, wherein R4 in formula (I) is C2-C3 alkenyl, preferably C2 alkenyl. Embodiment 18: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-17, wherein R5 in formula (I) is H. Embodiment 19: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-18, wherein R6 is –C1-C4 alkylene or –C3-C4 alkenylene, R7 is –C1-C4 alkyl or –C3-C4 alkenyl, R8 is –C1-C3 alkylene or –C3 alkenylene, and R9 is –C1-C3 alkyl or –C3 alkenyl; or 18    Docket No.: P243 00001‐WO‐PCT  R6 is –C1-C6 (preferably –C1-C4) alkylene, R7 is –C1-C6 (preferably –C1-C4) alkyl, R8 is –C1-C5 (preferably –C1-C3) alkylene, and R9 is –C1-C5 (preferably –C1-C3) alkyl. Embodiment 20: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-6, wherein the ether compound of formula (I) is chosen from 2-(Allyloxymethyl)-2-ethyl-1,3-propanediol, 2,2-bis(allyloxymethyl)-2-ethylpropanediol, 3-allyloxy-1,2-propanediol, 2,2-bis(hydroxymethyl)-1,3-propanediol allyl ether, and a combination thereof. Embodiment 21: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-20, wherein the ratio of the antimicrobial preservative to the ether compound of formula (I) ranges from about 1:50 to about 50:1, preferably from about 1:20 to about 20:1, from about 1:15 to about 15:1, from about 1:10 to about 10:1, or from about 1:5 to about 5:1. Embodiment 22: The antimicrobial composition of any one of Embodiments 1-21, wherein the antimicrobial composition contains greater than or equal to about 50 wt% of the antimicrobial preservative and the ether compound of formula (I) combined, based on the total weight of active ingredients in the antimicrobial composition, preferably from about 60 to 100 wt%, from about 70 to 100 wt%, from about 75 to 100 wt%, from about 80 to 100 wt%, from about 85 to 100 wt%, from about 90 to 100 wt%, or from about 95 or from about 97 to 100 wt%, based on the total weight of active ingredients in the antimicrobial composition. Embodiment 23: The antimicrobial composition of any one of Embodiments 1-22, wherein the antimicrobial composition comprises active ingredients consisting essentially of, or in further embodiments consisting of, the antimicrobial preservative and the ether compound of formula (I). Embodiment 24: The antimicrobial composition of any one of Embodiments 1-23, wherein the antimicrobial composition contains greater than or equal to about 50 wt% of the antimicrobial preservative and the ether compound of formula (I) combined, based on the total weight of the antimicrobial composition, preferably from about 60 to 100 wt%, from about 70 to 100 wt%, from about 75 to 100 wt%, from about 80 to 100 wt%, from about 85 to 100 wt%, from about 90 to 100 wt%, or from about 95 or from about 97 to 100 wt%, based on the total weight of the composition. Embodiment 25: The antimicrobial composition of any one of Embodiments 1-24, wherein the antimicrobial composition consists essentially of, or in further embodiments consists of, the antimicrobial preservative and the ether compound of formula (I). Embodiment 26: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises an isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), an alkylhydroxamic acid and/or salt thereof (e.g., 19    Docket No.: P243 00001‐WO‐PCT  hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid, salts thereof, combinations thereof, preferably caprylhydroxamic acid and/or a salt thereof), an aromatic aldehyde (e.g., cinnamic aldehyde), an alcohol (e.g., an aromatic alcohol, such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic alcohol, a phenolic compound, such as hydroxyacetophenone, combinations thereof), a diol (e.g., bronopol, glycols, such as 1,2-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., caprylyl glycol), combinations thereof), a glyceryl ether (e.g., ethylhexylglycerin, chlorphenesin), an aromatic ether (e.g., phenoxyethanol), a pyrithione (e.g., zinc pyrithione, sodium pyrithione), an organic acid (e.g., benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, combinations thereof), a salt and/or ester of an organic acid (e.g., esters and/or salts of the above organic acids, such as salts of sodium, potassium, calcium, magnesium or ammonium, including, e.g., sodium benzoate, potassium sorbate and the like, and esters of methyl, ethyl, propyl, isopropyl, butyl, isobutyl or phenyl, including butyl benzoate and the like), ethyl lauroyl arginate (LAE), or a combination thereof. Embodiment 27: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises an isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), an aromatic aldehyde (e.g., cinnamic aldehyde), an aromatic alcohol (e.g., benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic alcohol, a phenolic compound, such as hydroxyacetophenone, combinations thereof), an aromatic ether (e.g., phenoxyethanol), an organic acid (e.g., benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, combinations thereof), a salt or ester of an organic acid (e.g., esters and/or salts of the above organic acids, such as salts of sodium, potassium, calcium, magnesium or ammonium, including, e.g., sodium benzoate, potassium sorbate and the like, and esters of methyl, ethyl, propyl, isopropyl, butyl, isobutyl or phenyl, including butyl benzoate and the like), a pyrithione (e.g., zinc pyrithione, sodium pyrithione), ethyl lauroyl arginate (LAE) or a combination thereof. Embodiment 28: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises an alkylhydroxamic acid and/or salt thereof (preferably, hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid and/or salt thereof or combination thereof, particularly caprylhydroxamic acid and/or salt thereof), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., caprylyl glycol), bronopol, ethylhexylglycerin, chlorphenesin, CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic 20    Docket No.: P243 00001‐WO‐PCT  acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, a salt and/or ester of the foregoing acids, zinc pyrithione, sodium pyrithione or a combination thereof. Embodiment 29: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises caprylhydroxamic acid, phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenethyl alcohol, ethyl lauroyl arginate (LAE), CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, an ester or salt of said organic acids (e.g., sodium benzoate, potassium sorbate and the like), or a combination thereof; or the antimicrobial preservative comprises phenoxyethanol, benzyl alcohol, benzoic acid, a salt of benzoic acid (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT or a combination thereof. Embodiment 30: The product composition, method or use according to any one of Embodiments 2-21 and 26-29, wherein the ether compound of formula (I) is present in the product composition in an amount ranging from about 0.05 wt%, preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 10 wt%, preferably to about 5 wt%, more preferably to about 3 wt%, to about 2 wt%, in particular to about 1.5 wt%, or to about 1 wt%, based on the total weight of the product composition. Embodiment 31: The product composition, method or use according to any one of Embodiments 2-21 and 26-30, wherein the ether compound of formula (I) and the antimicrobial preservative are each present in the product composition in an amount ranging from about 0.05 wt%, preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 5 wt%, preferably to about 3 wt%, to about 2 wt%, more preferably to about 1.5 wt%, or to about 1 wt%, based on the total weight of the product composition. Embodiment 32: The product composition, method or use according to any one of Embodiments 2-21 and 26-31, wherein the ether compound of formula (I) and the antimicrobial preservative are present in the product composition in a combined amount of from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 10 wt%, preferably to about 5 wt%, more preferably to about 3 wt%, to about 2 wt%, to about 1.5 wt% or to about 1 wt%, based on the weight of the product composition. Embodiment 33: The product composition, method or use according to any one of Embodiments 2-21 and 26-32, wherein the ether compound of formula (I) and the antimicrobial preservative each is present in the product composition in an amount not exceeding 2 wt%, preferably not exceeding 1.5 wt% or not exceeding 1 wt%, based on the weight of the product composition. Embodiment 34: The product composition, method or use according to any one of Embodiments 2-21 and 26-33, wherein the combined amount of the ether compound of formula (I) and the antimicrobial preservative does not exceed 3 wt%, preferably does not exceed 2 wt%, such as from about 1.5 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.5 wt%), from about 1.2 wt% or 21    Docket No.: P243 00001‐WO‐PCT  less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.2 wt%) or from about 1 wt% or less (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1 wt%), based on the weight of the product composition. Embodiment 35: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-34, wherein the ether compound of formula (I) has one or more properties chosen from antioxidant, surfactant, humectant and chelating properties. Embodiment 36: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-12, wherein at least two of R1, R2, or R3 in formula (I) contain a –OH group (e.g., where R2 is –R6–OH and R3 is –OH or –R6–OH, preferably wherein R1 is H, –R6–OH, alkyl or alkenyl or is H, –R6–OH or –C1-C6 alkyl or –C1-C4 alkyl (e.g., methyl or ethyl)), and the ether compound of formula (I) has at least an antioxidant property, at least a chelating property, or at least an antioxidant property and a chelating property, wherein the antioxidant property is a μM Trolox equivalents (TE) value (i.e., μmol Trolox/L sample) of at least 25 μM TE, more preferably at least 50 μM TE or at least 75 μM TE, in particular at least 100 μM TE, at least 125 μM TE or at least 150 μM TE, and the chelating property is a μM EDTA equivalents value (i.e., µmol EDTA/L sample) of at least 50 μM EDTA equivalents, more preferably at least 75 μM EDTA equivalents or at least 100 μM EDTA equivalents, in particular at least 150 μM EDTA equivalents, at least 175 μM EDTA equivalents or at least 200 μM EDTA equivalents, where the Trolox equivalents value is determined according to the assay procedure of the Activated ABTS Antioxidant Assay Kit (Cat# AOX-14) (instruction manual ZBM0123.00, April 2021), and the EDTA equivalents value is determined according to the assay procedure of the Cupric Ion Chelating Assay Kit (Cat# AOX-16) (instruction manual ZBM0125.00, July 2021), preferably wherein R4 in formula (I) is C2-C3 alkenyl (in particular, C2 alkenyl), and further preferably wherein R5 in formula (I) is H. Embodiment 37: The product composition, method or use according to any one of Embodiments 2-12, wherein at least two of R1, R2, or R3 in formula (I) contain a –OH group (e.g., where R2 is –R6–OH and R3 is –OH or –R6–OH, preferably wherein R1 is H, –R6–OH, alkyl or alkenyl or is H, –R6–OH or –C1-C6 alkyl or –C1-C4 alkyl (e.g., methyl or ethyl)) and the amount of the ether compound of formula (I) (e.g., an amount according to any one or combination of Embodiments 30-34) provides at least an antioxidant property, at least a chelating property, or at least an antioxidant property and a chelating property to the product composition, wherein the antioxidant property provided to the product composition is an increase in the μM Trolox equivalents value of the composition (i.e., μmol Trolox/L sample) by at least 10%, more preferably by at least 15%, by at least 20% or by at least 25%, in particular by at least 30%, by at least 40% or by at least 50%, compared to the μM Trolox equivalents value of the composition in the absence of the ether compound of formula (I), and the chelating property provided to the product composition is an increase in the μM EDTA equivalents value of the composition (i.e., µmol EDTA/L sample) by at least 10%, more preferably by at least 15%, by at least 22    Docket No.: P243 00001‐WO‐PCT  20% or by at least 25%, in particular by at least 30%, by at least 40% or by at least 50%, compared to the μM EDTA equivalents value of the composition in the absence of the ether compound of formula (I), where the μM Trolox equivalents value of the product composition is determined according to the assay procedure of the Activated ABTS Antioxidant Assay Kit (Cat# AOX-14) (instruction manual ZBM0123.00, April 2021), and the μM EDTA equivalents value of the product composition is determined according to the assay procedure of the Cupric Ion Chelating Assay Kit (Cat# AOX-16) (instruction manual ZBM0125.00, July 2021), preferably wherein R4 in formula (I) is C2-C3 alkenyl (in particular, C2 alkenyl), and further preferably wherein R5 in formula (I) is H. Embodiment 38: The product composition, method or use according to any one of Embodiments 2-21 and 26-37, wherein the product composition is formulated as a liquid, paste, serum, hydrogel, cream, emulsion, lotion, gel, oil, wipe, ointment, semi-solid composition, or aerosol spray. Embodiment 39: The product composition, method or use according to any one of Embodiments 2-21 and 26-38, wherein the product composition is a personal care or cosmetic product chosen from shampoos, conditioners, shower gels, liquid soaps, skin lotions, liquids for a wet wipe, face creams, hair treatments, makeup, and makeup removers. Unless otherwise specified, the following terms are defined as follows: As used herein, the articles “a”, “an”, and “the” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e., occurrences) of the element or component. Therefore “a”, “an”, and “the” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. As used herein, the term “alkyl” means a monovalent linear or branched saturated hydrocarbon having the specified number of carbons. As used herein, the term “alkylene” means a divalent linear or branched saturated hydrocarbon having the specified number of carbons. As used herein, the term “alkenyl” means a monovalent linear or branched hydrocarbon having at least one carbon-carbon double bond. As used herein, the term “alkenylene” means a divalent linear or branched hydrocarbon having at least one carbon-carbon double bond. As used herein, the term “comprising” means the presence of the stated features, integers, steps, or components as referred to in the claims, but does not preclude the presence or addition of one or more other features, integers, steps, components or groups thereof. The term “comprising” is intended to include embodiments encompassed by the terms “consisting essentially of” and “consisting of,” unless the context dictates otherwise. 23    Docket No.: P243 00001‐WO‐PCT  As used herein, the term “about” modifying the quantity of an ingredient or reactant employed refers to variation in the numerical quantity that can occur, for example, through typical measuring and liquid handling procedures used for making concentrates or use solutions in the real world; through inadvertent error in these procedures; through differences in the manufacture, source, or purity of the ingredients employed to make the compositions or carry out the methods; and the like. Where present, all ranges are inclusive and combinable. For example, when a range of “1 to 5” is recited, the recited range should be construed as including ranges “1 to 4”, “1 to 3”, “1-2”, “1-2 & 4- 5”, “1-3 & 5”, and the like. When a parameter is given either as a range, preferred range, or a list of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. Where a range of numerical values is recited herein, unless otherwise stated, the range is intended to include the endpoints thereof, and all integers and fractions within the range. The scope of the invention is not intended to be limited to the specific values and examples as recited in the specification. EXAMPLES The following examples demonstrate that the ether compounds of the present disclosure, when incorporated into various product formulations, surprisingly improved the preservation efficacy of traditional and soft antimicrobial preservatives, including, but not limited to, phenoxyethanol, sodium benzoate, benzyl alcohol, Ethyl lauroyl arginate (LAE), and 2-methyl-4-isothiazolin-3-one (MIT), against a full spectrum of different bacteria and fungi, thereby enabling reduction in required traditional or soft preservative levels for protecting such products against microbial growth. Ether compounds of the present disclosure further surprisingly (i) showed significant antioxidant properties based on determined Trolox equivalent values and provided antioxidant properties to product compositions; (ii) showed humectant properties as demonstrated by reduced water activity (measured by Rotronic Water Activity Meter) comparable to known moisturizing ingredients such as ethyl hexyl glycerin; (iii) reduced the surface tension after dosing into water, demonstrating surfactant properties; and (iv) showed significant chelating properties based on determined EDTA equivalent values. Compounds representative of the presently disclosed ether compounds and used in the following experimental examples are shown in Table 1. 24    Docket No.: P243 00001‐WO‐PCT  Table 1. Compound Name Structure Compound 1 2-(Allyloxymethyl)-2-ethyl-1,3-
Figure imgf000026_0001
Example 1. Challenge testing to demonstrate preservation enhancement of traditional and soft preservatives. The preservative activity in representative rinse-off and leave-on product compositions was evaluated using a modification of the Personal Care Products Council (PCPC) protocol (Machtiger, et al. 2001. Determination of the Efficacy of Preservation of Non-Eye Area Water Miscible Cosmetic and Toiletry Compositions: Collaborative Study. J of AOAC International. 84:1, 101-109). This evaluation was conducted using a four week, two-cycle microbial preservative efficacy test (challenge test) at 25 ^C to determine the preservative efficacy of each treatment. The presently disclosed ether compounds were tested alone and in combination with certain antimicrobial preservatives in various product formulations. The compounds were dosed and mixed thoroughly at room temperature into the different compositions, including a lotion with carbomer (leave-on, Table 2), and a serum composition with xanthan gum (leave-on , Table 3), a body wash formulation (rinse- off , Table 4), and a cream formulation (leave-on, Table 5). Table 2 shows an exemplary composition for carbomer-based anionic lotion compositions. Carbomers are commonly used as a synthetic rheological modifier in personal care products. The composition below was made by heating the aqueous (A) and oil (B) phases separately to 75-80 °C. The oil phase was then poured into the aqueous phase and mixed by an overhead mixer and a homogenizer. The oil- in-water emulsion was cooled to room temperature. Triethanolamine was used to adjust the pH to 6.0- 6.5. 25    Docket No.: P243 00001‐WO‐PCT  Table 2. Representative Lotion Composition with Carbomer Phase Ingredients INCI Name WT % A Water Water 88.6
Figure imgf000027_0001
by adding all the ingredients into a beaker and mixing with an overhead mixer and heating to 75-80 °C. The mixture was homogenized and cooled to room temperature. The pH was adjusted with a sodium hydroxide solution to pH 5.0~5.5. Table 3. Representative Serum Composition with Xanthan Gum Ingredients INCI Name WT 0
Figure imgf000027_0002
    Docket No.: P243 00001‐WO‐PCT  XIAMETER PMX-200 Dimethicone 2.00 Silicone Fluid 100 cSt
Figure imgf000028_0001
ACULYN 88 and water in a beaker and then adding STEOL 230 and AMPHOSOL CA. The solution was mixed with an overhead mixer. Triethanolamine was used to adjust the final pH to 6.8. Table 4. Representative Body Wash Formulation Ingredients INCI Name WT % Deionized water Deionized water 70.5 Ta
Figure imgf000028_0002
by heating the aqueous (A) and oil (B) phases separately to 75-80 °C. The oil phase was then poured into the aqueous phase and mixed by an overhead mixer and a homogenizer. The oil-in-water emulsion was cooled to room temperature. SEPIGEL 305 was then added into the emulsion. Sodium hydroxide solution was used to adjust the final pH to 5.0. Table 5. Representative Nonionic Cream Formulation Phase Ingredients INCI Name WT % A 1
Figure imgf000028_0003
After dosing, the samples were divided into two separate aliquots of 5 gram each. One aliquot was inoculated with 50 µl of a diluted bacterial pool, and the second aliquot was inoculated with 50 µL of 27    Docket No.: P243 00001‐WO‐PCT  a diluted fungal pool as described below. Unpreserved product samples were included in the test as a growth control. A mixed bacterial inoculum was prepared using 24-hour cultures of the test bacteria (Table 6) grown in trypticase soy broth (TSB). Equal volumes of the bacterial test strains were combined and diluted one to ten in phosphate buffer to obtain an inoculum of approximately 5 x 107 to 5 x 108 colony forming units per mL (cfu/mL). The test samples were inoculated with 1% of the mixed bacterial inoculum. A mixed fungal inoculum was prepared using cell suspensions of the yeast Candida albicans ATCC # 10231 and the mold Aspergillus brasiliensis ATCC #16404 in phosphate buffer. Equal volumes of the fungal test strains were combined and diluted one to ten with phosphate buffer to obtain an inoculum of approximately 5 x 106 to 5 x 107 cfu/mL. The test samples were inoculated with 1% of the mixed fungal inoculum. Table 6. Mixed Bacterial Inoculum Microorganism ATCC Number Type Burkholderia cepacian 25416 Gram-Negative Non-fermenter
Figure imgf000029_0001
e sampes were su jecte to m cro a c a enge at t me zero an nocuate a secon t me a ter seven days. The number of microorganisms added to each sample was determined by a standard Most Probable Number (MPN) determination in Trypticase Soy Broth (TSB) for bacteria and Potato Dextrose Broth (PDB) for fungi. Samples were incubated at 25 °C for the test duration of four weeks. Samples were monitored for bacterial and fungal contamination after 2, 7, 14, 21, and 28 days. Samples challenged with bacteria were streak-plated onto Trypticase Soy Agar (TSA) and incubated at 30 °C for 24 hours. Samples challenged with fungi were streak-plated onto Potato Dextrose Agar (PDA) and incubated at 25 °C for 7 days. After incubation, plates were given a Growth Rating to determine the colony forming units per gram (CFU/g) present in each test sample at the testing time point. Table 7 represents the growth score. A rating of excellent, good, and adequate were all considered to be a pass for the challenge test. As is used by various challenge test methods, the passing criteria was more stringent for bacteria than for fungi. A rating of 2, 3, or 4 at 21 and/or 28 28    Docket No.: P243 00001‐WO‐PCT  days was considered a failure for bacteria. For fungi, a rating of 2 at 21 and/or 28 days was considered a pass. Table 7. Growth Score Used to Determine CFU/mL in Test Samples. Growth Description of Microbial Growth Plating Results Approximate cfu/g Rating
Figure imgf000030_0001
growth rating score caused by bacteria of 1 or less at days 21-28 of the testing period and was scored as “Fail” if the composition obtained a growth rating score caused by bacteria of 2 or more at days 21- 28 of the testing period. For fungi challenge testing, a composition was scored as “Pass” if the composition obtained a growth rating score caused by fungi of 2 or less at days 21-28 of the testing period and was scored as “Fail” if the composition obtained a growth rating score caused by fungi of more than 2 at days 21-28 of the testing period. The “Pass” rating of a dosed composition was also contingent upon the unpreserved sample having a rating of “Fail”. Example 1A A representative leave-on lotion formulation was made according to Table 2. As shown in Table 8, none of the lotion formulations passed the challenge test when dosed with either phenoxyethanol (POE), benzyl alcohol (BA) or the compounds in Table 1 alone. However, when dosed with a combination of phenoxyethanol or benzyl alcohol and the respective Compounds 1 to 4, the lotion formulations showed significantly enhanced antimicrobial properties against both bacteria and fungi, each achieving a passing rating in the challenge testing. This example demonstrates that the ether compounds of the present disclosure enhance the efficacy of soft preservatives, such as phenoxyethanol and benzyl alcohol, and advantageously so such that efficacious antimicrobial activity can be achieved at reduced dosing levels of soft preservatives (e.g., 0.3% to 0.5% or to 0.4%). Table 8. Challenge test data – lotion formulation comprising carbomer Bacteria growth Fungi growth rating
Figure imgf000030_0002
29    Docket No.: P243 00001‐WO‐PCT  Sample and Dosing (wt%) D21 D28 Result D21 D28 Result Overall Result
Figure imgf000031_0001
Docket No.: P243 00001‐WO‐PCT  Example 1B A representative serum formulation comprising xanthan-gum was made according to Table 3. As shown in Table 9, none of the serum formulations passed the challenge test when dosed with either phenoxyethanol (POE), benzyl alcohol, sodium benzoate, or Compound 1 in Table 1 alone. However, when dosed with a combination of phenoxyethanol and Compound 1, with a combination of benzyl alcohol and Compound 1, and with a combination of sodium benzoate and Compound 1, the respective formulations showed significantly enhanced antimicrobial properties against both bacteria and fungi. This example demonstrates the enhanced efficacy of soft preservatives, such as phenoxyethanol, benzyl alcohol, and sodium benzoate, when combined with the ether compounds of the present disclosure, and advantageously so such that efficacious antimicrobial activity can be achieved at reduced dosing levels of soft preservatives (e.g., 0.2-0.5%). Table 9. Challenge test data – serum composition comprising xanthan gum Bacteria growth Fungi growth rating rating ll t
Figure imgf000032_0001
Example 1C A representative rinse-off body wash formulation was made according to Table 4. As shown in Table 10, none of the body wash formulations passed the challenge test when dosed with either 31    Docket No.: P243 00001‐WO‐PCT  phenoxyethanol (POE), benzyl alcohol, or Compound 1 in Table 1 alone. However, when dosed with a combination of phenoxyethanol and Compound 1 or with a combination of benzyl alcohol and Compound 1, the respective body wash formulations showed significantly enhanced antimicrobial properties against both bacteria and fungi. This example demonstrates the enhanced efficacy of soft preservatives, such as phenoxyethanol and benzyl alcohol, when combined with the ether compounds of the present disclosure, and advantageously so such that efficacious antimicrobial activity can be achieved at reduced dosing levels of soft preservatives (e.g., 0.3 to 0.5% or to 0.4%). Table 10. Challenge test data – body wash formulation Bacteria growth Fungi growth rating rating
Figure imgf000033_0001
Example 1D Traditional isothiazolinone preservatives, such as 2-methyl-4-isothiazolin-3-one (i.e., methylisothiazolinone, MIT), are commonly used to protect personal and home care products from bacteria. Table 11 shows an example of using Compound 1 in Table 1 to enhance the antimicrobial performance of MIT in a representative lotion formulation (Table 2). When used alone at either 5 or 10 ppm, MIT failed to preserve the lotion formulation against bacteria. When MIT was combined with Compound 1 dosed at a level of 0.5%, the preservation performance of MIT was significantly enhanced, and the lotion formulation was successfully preserved against bacteria. Table 11. Challenge test data – lotion formulation comprising carbomer 32    Docket No.: P243 00001‐WO‐PCT  Bacteria growth rating Sample and Dosing (wt%) D7 D14 D21 D28 Result
Figure imgf000034_0001
Ethyl lauroyl arginate (LAE) is a cationic preservative commonly used in food, home and personal care applications. Table 12 shows an example of using Compound 1 in Table 1 to enhance the antimicrobial performance of LAE in a nonionic cream formulation (Table 5). When used alone from 1000 to 4000 ppm, LAE failed to preserve the lotion formulation against bacteria. When LAE at 4000 ppm was combined with Compound 1 dosed at a level of 0.5%, the preservation performance of LAE was significantly enhanced, and the cream formulation was successfully preserved against bacteria. Table 12. Challenge test data – nonionic cream formulation Bacteria growth rating
Figure imgf000034_0002
Example 1F Ethylhexylglycerin (EHG) and pentylene glycol (1,2-pentanediol) are commercially available multifunctional ingredients often used to enhance the antimicrobial performance of soft preservatives, such as phenoxyethanol. Table 13 shows an example of using Compound 1 in Table 1 to enhance the antimicrobial performance of phenoxyethanol, as compared against EHG and pentylene glycol as commercial benchmarks, in a representative lotion formulation (Table 2). Compound 1 exhibited 33    Docket No.: P243 00001‐WO‐PCT  superior antimicrobial enhancement of POE as compared to either of ethylhexylglycerin or pentylene glycol (Table 13). Table 13. Challenge test data – lotion formulation Bacteria growth rating Sample and Dosing (wt%) D7 D14 D21 D28 Result
Figure imgf000035_0001
Antioxidant properties were studied using the Activated ABTS Antioxidant Assay Kit (Cat# AOX-14, instruction manual ZBM0123.00, April 2021) from Zen-Bio for the following experiments. The water-soluble analogue of α-tocopherol (a commonly known vitamin E antioxidant), Trolox, was used as a reference. Antioxidant properties were studied both intrinsically and in hydrogel and micellar water personal care compositions. The hydrogel and micellar water compositions are shown in Table 14 and Table 15, respectively. The hydrogel composition was made by sprinkling the xanthan gum powder slowly into a beaker with constant mixing. The mixture was then heated to 75~80 °C and mixed until no evidence of phase separation. The hydrogel was then cooled to room temperature and speed-mixed to remove bubbles. The micellar water composition was made by adding all the ingredients into a beaker and heating the ingredient mixture to 75~80 °C. The final product was cooled to room temperature and pH was adjusted to 5-5.5 with citric acid solution. Sample compounds were dosed into the compositions at the desired weight percent by using a speed mixer. Table 14. Hydrogel Composition with Xanthan Gum Ingredients INCI Name WT %
Figure imgf000035_0002
34    Docket No.: P243 00001‐WO‐PCT  Xanthan gum Xanthan gum 0.50
Figure imgf000036_0001
Ingredients INCI Name WT % Water Aqua 92.95
Figure imgf000036_0002
0 μM) were used as the calibration curve for quantifying the antioxidant properties. The absorbance of the Trolox and the multifunctional additives were measured in triplicates using the Multimode Microplate Reader, BioTek Synergy H1, at a wavelength of 405 nm. Table 16 summarizes the intrinsic antioxidant property of each of Compounds 1-4 based on the Trolox equivalents values determined using the Activated ABTS test. As shown in Table 16, based on the determined Trolox equivalents values, the alkenyl (e.g., allyl) ether compounds of the present disclosure, in particular where at least two of R1, R2 or R3 contain an OH group, exhibit significant antioxidant properties (i.e., in this Example, Compounds 1, 3 and 4). As a comparison, pentylene glycol (a preservative or preservative enhancer commonly used in personal care and cosmetic products) and benzyl alcohol (a soft preservative commonly used in personal care and cosmetic products) showed minimal antioxidant property as indicated by the low Trolox equivalents values. In addition, blends of Compound 1 /pentylene glycol (50% w/w, “Combo 1” in Table 16) and Compound 1/benzyl alcohol (50% w/w, “Combo 2” in Table 16) both showed higher Trolox equivalents values than the individual ingredients. This example demonstrates the antioxidant properties of the presently disclosed ether compounds and the further antioxidant performance benefit of blending such compounds with representative preservatives. Table 16. Trolox equivalents (calculated from a Trolox calibration curve) Sample Ingredient and weight precent μM Trolox equivalents )
Figure imgf000036_0003
35    Docket No.: P243 00001‐WO‐PCT  Compound 2 2,2-Bis(allyoxymethyl)-2-ethylpropanediol 0 ± 6 Compound 3 Pentaerythritol allyl ether 150 ± 2 Compou
Figure imgf000037_0001
speed mixer. The hydrogel compositions were all diluted by the assay buffer at 5-fold dilution to make the final solution fully transparent, while running the Activated ABTS Assay (i.e., Cat# AOX- 14, instruction manual ZBM0123.00, April 2021) to ensure the composition (e.g., translucency) did not contribute to the antioxidant properties. As shown in Table 17, blank hydrogel composition after 5-fold dilution showed no antioxidant property. In contrast, hydrogel composition dosed with Compound 1 after 5-fold dilution showed increasing values of the Trolox equivalent. This further demonstrates the antioxidant benefits associated with the presently disclosed ether compounds. Table 17. Trolox equivalents (calculated from a Trolox calibration curve) of the hydrogel Sample and dosing level in wt% μM Trolox equivalents (μmol Trolox/L sample) Compou
Figure imgf000037_0002
nd 1 was dosed at different concentrations into the micellar water composition above by using a speed mixer. The micellar water compositions were all transparent. As shown in Table 18, the blank micellar water showed antioxidant property with a Trolox equivalents value of 72 ± 1 μM because of the antioxidant property of the ingredients (such as propylene glycol, disodium EDTA, and panthenol) used in the composition (Table 15). After being dosed with Compound 1, the micellar water showed an increase of Trolox equivalents values as the dosing level increased. This further demonstrates the antioxidant benefits associated with the presently disclosed ether compounds. Table 18. Trolox equivalents (calculated from a Trolox calibration curve) of the micellar water sample. 36    Docket No.: P243 00001‐WO‐PCT  Sample and dosing level in wt% μM Trolox equivalents (μmol Trolox/L sample) Exampl
Figure imgf000038_0001
Surface tension of an aqueous solution was measured by using the Wilhelmy plate method on a Krüss K100 Force Tensiometer, equipped with a platinum plate. As shown in Table 19, addition of Compound 1 in Table 1 reduced the surface tension of the aqueous solution. This demonstrates the surfactant properties associated with the presently disclosed ether compounds. Surfactants are commonly used in personal care products to, for example, stabilize leave-on compositions and create cleansing foams in rinse-off compositions. Table 19. Surface tensions of water Concentration [mg/L] of Compound 1 Surface tension [mN/m] 0 726
Figure imgf000038_0002
Oil-water interfacial tension of test and control samples was measured by a Krüss K100 Force Tensiometer equipped with Du Noüy ring (platinum-iridium ring) using ring tear off method by the inbuild software. The force maximum was determined with a modern tensiometer with an electronic force sensor, and the ring was cleaned and dried before each measurement. All measurements were 37    Docket No.: P243 00001‐WO‐PCT  made at room temperature. As shown in Table 20, the addition of Compound 1 in Table 1 significantly reduced the interfacial tension between the oil and water interface. When Compound 1 (0.5 wt%) was dosed together with a representative soft preservative, phenoxyethanol (0.5 wt%, for a combined total of 1 wt%), the interfacial tension was lower than the samples dosed with either of 1 wt% of phenoxyethanol or 1 wt% of Compound 1, which demonstrates a synergistic emulsifying property of the presently disclosed ether compound when combined with soft preservatives, such as phenoxyethanol. Table 20. interfacial tensions between mineral oil and water Phases Dosed additives and percent level Interfacial Tension (mN/m)
Figure imgf000039_0001
xamp e : umectant propert es Glycerin and 2-ethylhexylglycerin are humectants commonly used in personal care compositions. Water activity of 10 and 20 wt% aqueous multifunctional dispersion was measured using AwTherm, ROTRONIC water activity at the equilibrium setting. The water activity meter was pre-calibrated with humidity standards and all measurements were performed at 25 °C. Water activity parameter was the equilibrated relative humidity of a given sample divided by 100 and the value ranged from 0 to 1. The parameter was the measure of unbound water molecule in a system and provided a measure of the ability of the system to adsorb water and act as humectant. As shown in Table 21, Compounds 1 to 4 in Table 1 showed comparable water activity reduction at 10 wt% as compared against the two benchmarks glycerin and 2-ethylhexylglycerin. At 20 wt%, glycerin showed the largest reduction of the water activity as a result of solubility limitations of the 38    Docket No.: P243 00001‐WO‐PCT  other samples. This example demonstrates that the ether compounds of the present disclosure can be used as a humectant, particularly at dosing levels at or less than 10%. Table 21. water activity measurement Sample % Reduction of the Water % Reduction of the Water activity (aw), 10 wt% in activity (aw), 20 wt% in water water
Figure imgf000040_0001
Example 5: Chelation properties Chelation properties were measured using the ZenBio Cupric Ion Chelating (CIC) Assay (Cat# AOX- 16, instruction manual ZBM0125.00, July 2021). The assay measured the capacity of the samples to chelate free cupric ions in solution, thereby inhibiting Cu(II) binding to pyrocatechol violet (PV) for generating a highly colored complex. The absorbance of the Cupric-PV complex was measured at a wavelength of 632 nm. The Cupric Ion Chelating activity was determined as the percent of total PV over the Cu(II) binding. Ethylenediaminetetraacetic acid (EDTA), a well-known chelating agent, was used as a positive control. A series of EDTA with 7 different concentrations from 0 to 1000 µM were prepared and their corresponding absorbance measured and used as the calibration curve (Cupric ion chelating (%) vs. EDTA concentration). Percent Cupric ion chelating was determined applying the following calculations and equation 1. The background absorbance value was determined by averaging the absorbance values of the three background wells (no CuSO4 or sample). The average background absorbance was then subtracted from all of the sample absorbance values. The maximal absorbance value (Absmax) was determined by averaging the absorbance values of the three wells containing CuSO4, PV and assay buffer. Abstest in equation 1 was the absorbance of the test sample. Cupric ion chelating (%) = 100 × (Absmax – Abstest)/Absmax (Equation 1) The calibration curve (Cupric ion chelating (%) vs. EDTA concentration) was fit using a polynomial curve after log10 transforming the concentrations (R2>0.98). The chelating activity of each of Compounds 1-4 from Table 1 is shown in Table 22. Based on the determined EDTA equivalents values, the alkenyl (e.g., allyl) ether compounds of the present 39    Docket No.: P243 00001‐WO‐PCT  disclosure, in particular where at least two of R1, R2 or R3 contain an OH group, exhibit significant chelating properties (i.e., in this Example, Compounds 1, 3 and 4). For comparison, both ethylhexylglycerin (commonly used as part of a preservative system in personal care and cosmetic formulations) and phenoxyethanol (a representative soft preservative commonly used in personal care and cosmetic formulations) did not show a chelating property, with a negligible Cupric ion chelating (%) value (slightly negative) after subtracting the background absorbance (i.e., approximately 0 μM of the EDTA equivalents). Table 22. EDTA equivalents (calculated from a EDTA calibration curve) Sample Cupric ion chelating (%) μM EDTA equivalents (µmol EDTA/L sample)
Figure imgf000041_0001
40   

Claims

Docket No.: P243 00001‐WO‐PCT  What is claimed is: 1. A personal care, cosmetic or home care product composition comprising an antimicrobial preservative and an ether compound of formula (I) ,
Figure imgf000042_0001
alkenyl, –R6–OH, or –R8–O–R9; R2 is –C1-C6 alkyl, –C2-C6 alkenyl, –R6–OH, –O–R7, or –R8–O–R9; R3 is –OH, –R6–OH, –O–R7 or –R8–O–R9; R4 is –C2-C5 alkenyl; and R5 is H, –C1-C5 alkyl, or –C2-C5 alkenyl; and, with respect to R1, R2 and R3 independently of one another, R6 is –C1-C6 alkylene or –C3-C6 alkenylene, R7 is –C1-C6 alkyl or –C3-C6 alkenyl, R8 is –C1-C5 alkylene or –C3-C5 alkenylene, and R9 is –C1-C5 alkyl or –C3-C5 alkenyl; and at least one of R1, R2 or R3 contains a –OH group. 2. The composition of claim 1, wherein at least one of R1, R2 or R3 contains an ether group. 3. The composition of claim 1 or 2, wherein at least two of R1, R2, or R3 contain a –OH group. 4. The composition of claim 1, wherein R1, R2, and R3 each contains a –OH group. 5. The composition of claim 1, wherein R2 is R6–OH, and R3 is –OH or –R6–OH. 6. The composition of claim 1, wherein R2 is O–R7 or –R8–O–R9, and R3 is –OH or –R6–OH. 7. The composition of any preceding claim, wherein R1 is H, –C1-C6 alkyl or –R6–OH. 8. The composition of any preceding claim, wherein R4 is C2-C3 alkenyl, preferably C2 alkenyl. 9. The composition of any preceding claim, wherein R5 is H. 10. The composition of any preceding claim, wherein R6 is –C1-C4 alkylene or –C3-C4 alkenylene; R7 is –C1-C4 alkyl or –C3-C4 alkenyl; R8 is –C1-C3 alkylene or –C3 alkenylene; and R9 is –C1-C3 alkyl or –C3 alkenyl. 11. The composition of claim 1, wherein the ether compound of formula (I) is chosen from 2-(Allyloxymethyl)-2-ethyl-1,3-propanediol, 2,2-bis(allyloxymethyl)-2-ethylpropanediol, 3-allyloxy-1,2-propanediol, 2,2-bis(hydroxymethyl)-1,3-propanediol allyl ether, and a combination thereof. 41    Docket No.: P243 00001‐WO‐PCT  12. The composition of any preceding claim, wherein the antimicrobial preservative comprises an isothiazolinone, an alkylhydroxamic acid and/or salt thereof, an aromatic aldehyde, an alcohol, a diol, a glyceryl ether, an aromatic ether, a pyrithione, an organic acid, a salt and/or ester of an organic acid, ethyl lauroyl arginate (LAE), or a combination thereof, preferably wherein the antimicrobial preservative comprises an isothiazolinone, an aromatic aldehyde, an aromatic alcohol, an aromatic ether, an organic acid, a salt or ester of an organic acid, a pyrithione, ethyl lauroyl arginate (LAE) or a combination thereof. 13. The composition of any preceding claim, wherein the antimicrobial preservative comprises an alkylhydroxamic acid and/or salt thereof, phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, bronopol, ethylhexylglycerin, chlorphenesin, CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, a salt and/or ester of the foregoing acids, zinc pyrithione, sodium pyrithione, or a combination thereof. 14. The composition according to any preceding claim, wherein the antimicrobial preservative comprises caprylhydroxamic acid, phenoxyethanol, benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenethyl alcohol, ethyl lauroyl arginate (LAE), CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, an ester or salt of said organic acids, or a combination thereof, preferably wherein the antimicrobial preservative comprises phenoxyethanol, benzyl alcohol, benzoic acid, a salt of benzoic acid, ethyl lauroyl arginate, CMIT, MIT, BIT or a combination thereof. 15. The composition of any preceding claim, wherein the composition comprises the ether compound of formula (I) in an amount of from about 0.01 wt% to about 5 wt%, based on the total weight of the composition. 16. The composition of any preceding claim, wherein the ether compound of formula (I) has one or more properties chosen from antioxidant, surfactant, humectant and chelating properties. 17. A method of providing antimicrobial activity to a personal care, cosmetic or home care product composition, comprising adding to the composition an antimicrobial preservative and an ether compound of formula (I) (I),
Figure imgf000043_0001
wherein R1 is H, –C1-C6 alkyl, –C2-C6 alkenyl, –R6–OH, or –R8–O–R9; R2 is –C1-C6 alkyl, –C2-C6 alkenyl, –R6–OH, –O–R7, or –R8–O–R9; 42    Docket No.: P243 00001‐WO‐PCT  R3 is –OH, –R6–OH, –O–R7 or –R8–O–R9; R4 is –C2-C5 alkenyl; and R5 is H, –C1-C5 alkyl, or –C2-C5 alkenyl; and, with respect to R1, R2 and R3 independently of one another, R6 is –C1-C6 alkylene or –C3-C6 alkenylene; R7 is –C1-C6 alkyl or –C3-C6 alkenyl; R8 is –C1-C5 alkylene or –C3-C5 alkenylene; and R9 is –C1-C5 alkyl or –C3-C5 alkenyl; and at least one of R1, R2 or R3 contains a –OH group. 18. A method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition, comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) (I),
Figure imgf000044_0001
R1 H, C6 alkenyl, –R6–OH, or –R8–O–R9; R2 is –C1-C6 alkyl, –C2-C6 alkenyl, –R6–OH, –O–R7, or –R8–O–R9; R3 is –OH, –R6–OH, –O–R7 or –R8–O–R9; R4 is –C2-C5 alkenyl; and R5 is H, –C1-C5 alkyl, or –C2-C5 alkenyl; and, with respect to R1, R2 and R3 independently of one another, R6 is –C1-C6 alkylene or –C3-C6 alkenylene, R7 is –C1-C6 alkyl or –C3-C6 alkenyl, R8 is –C1-C5 alkylene or –C3-C5 alkenylene, and R9 is –C1-C5 alkyl or –C3-C5 alkenyl; and at least one of R1, R2 or R3 contains a –OH group. 19. Use of an ether compound of formula (I) for enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or home care product composition: ,
Figure imgf000044_0002
alkenyl, –R6–OH, or –R8–O–R9; 43    Docket No.: P243 00001‐WO‐PCT  R2 is –C1-C6 alkyl, –C2-C6 alkenyl, –R6–OH, –O–R7, or –R8–O–R9; R3 is –OH, –R6–OH, –O–R7 or –R8–O–R9; R4 is –C2-C5 alkenyl; and R5 is H, –C1-C5 alkyl, or –C2-C5 alkenyl; and, with respect to R1, R2 and R3 independently of one another, R6 is –C1-C6 alkylene or –C3-C6 alkenylene, R7 is –C1-C6 alkyl or –C3-C6 alkenyl, R8 is –C1-C5 alkylene or –C3-C5 alkenylene, and R9 is –C1-C5 alkyl or –C3-C5 alkenyl; and at least one of R1, R2 or R3 contains a –OH group. 20. An antimicrobial composition comprising an antimicrobial preservative and an ether compound of formula (I) (I),
Figure imgf000045_0001
R1 H, C6 alkenyl, –R6–OH, or –R8–O–R9; R2 is –C1-C6 alkyl, –C2-C6 alkenyl, –R6–OH, –O–R7, or –R8–O–R9; R3 is –OH, –R6–OH, –O–R7 or –R8–O–R9; R4 is –C2-C5 alkenyl; and R5 is H, –C1-C5 alkyl, or –C2-C5 alkenyl; and, with respect to R1, R2 and R3 independently of one another, R6 is –C1-C6 alkylene or –C3-C6 alkenylene, R7 is –C1-C6 alkyl or –C3-C6 alkenyl, R8 is –C1-C5 alkylene or –C3-C5 alkenylene, and R9 is –C1-C5 alkyl or –C3-C5 alkenyl; and at least one of R1, R2 or R3 contains a –OH group, wherein at least 75 wt%, preferably at least 90 wt%, based on the total weight of active ingredients in the antimicrobial composition, constitutes the combined amount of the antimicrobial preservative and the ether compound of formula (I). 44   
PCT/US2023/036733 2022-11-10 2023-11-03 Multifunctional boosters for antimicrobial preservatives and applications thereof WO2024102302A1 (en)

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