Multifunctional boosters for antimicrobial preservatives and their applications

Abstract

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

Description

[Technical Field]

[0001] The present invention relates generally to multifunctional boosters for enhancing the antimicrobial activity of antimicrobial preservatives and their applications in personal care, cosmetic and home care products, and more particularly to certain ether compounds as such multifunctional boosters. [Background technology]

[0002] Protection of personal care products, cosmetics, and home care products from microbial contamination is of high importance in these product industries. Traditional preservatives, such as isothiazolinones, formaldehyde-releasing agents, parabens, and IPBC, are under increasing scrutiny from regulatory agencies and environmental working groups. Product formulators are often seeking solutions to reduce the dosage levels of traditional preservatives without compromising preservative levels. Many product formulators are also beginning to turn to "soft" preservatives, such as phenoxyethanol, alcohols, and / or organic acids. Because soft preservatives alone often do not provide strong, broad-spectrum antimicrobial efficacy, especially at desirable dosage levels, formulators may use them in combination with booster compounds to provide stronger protection to product compositions.

[0003] Furthermore, many product compositions contain ingredients that 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 can also have unintended, undesirable effects, including, for example, increased stickiness or a tendency to form residue, and reduced desirable sensory or handling properties as perceived by consumers. Furthermore, there is a growing demand for product formulations that provide multiple benefits within a single product or product application.

[0004] WO2014 / 191258 A2 is directed to antimicrobial compositions containing certain glyceryl ethers, and WO2022 / 128882 A1 is directed to combinations of n-heptyl-glyceryl ethers with 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 enhancement of the activity of antimicrobial preservatives by the compounds of the present invention, or their multifunctional properties, as described herein. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] WO2014 / 191258 A2 [Patent Document 2] WO2022 / 128882 A1 [Non-patent literature]

[0006] [Non-Patent Document 1] 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, pp. 101-109. Summary of the Invention [Problem to be solved by the invention]

[0007] There is a need to provide booster compounds that enhance the antimicrobial effectiveness of antimicrobial preservatives in personal care, cosmetic, and home care product compositions, thereby reducing the number and / or concentration of antimicrobial preservatives normally required to achieve adequate protection. Additionally, there is a need to provide compounds that have multifunctional benefits, such as antioxidant, surfactant, moisturizing, and / or chelating properties, thereby allowing formulators to formulate products with a reduced number and / or amount of ingredients without compromising (and potentially even enhancing) the benefits of the final product. [Means for solving the problem]

[0008] 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 enabling a broad spectrum of antimicrobial efficacy to be achieved while reducing the number and / or concentration of antimicrobial preservatives normally required to achieve sufficient broad spectrum protection. The present disclosure is further based on the discovery of the multifunctional nature of the inventively disclosed ether compounds, as it has surprisingly been found that such compounds can exhibit and provide one or more additional properties to product formulations, such as one or more of antioxidant properties, surfactant properties, moisturizing properties, and / or chelating properties.

[0009] Antimicrobial preservatives and a composition of formula (I)

[0010] [ka]

[0011] [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; R3 is -OH, -R6-OH, -O-R7 or -R8-O-R9; R4 is -C2-C5 alkenyl; 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 an —OH group.

[0012] In another aspect, a method of providing antimicrobial activity to a personal care, cosmetic, or home care product composition (e.g., to control or inhibit the growth of microorganisms in the product composition) comprises adding to the composition an antimicrobial preservative and an ether compound of Formula (I) described herein.

[0013] In a further aspect, the present disclosure provides the use of an ether compound of formula (I) as described herein to enhance the antimicrobial efficacy of an antimicrobial preservative in a personal care product, cosmetic or home care product composition.

[0014] In another aspect, there is provided a method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care product, cosmetic, or home care product composition, comprising combining or mixing the antimicrobial preservative with an ether compound of Formula (I) described herein, wherein the antimicrobial efficacy is enhanced compared to an equal amount of the antimicrobial preservative without the ether compound.

[0015] In a further aspect, there is provided a method of reducing the minimum amount of antimicrobial preservative required for preservative activity in a personal care product, cosmetic or home care product composition, comprising the step of combining or mixing an antimicrobial preservative with an ether compound of Formula (I) described herein, wherein after said step of combining or mixing with the ether compound, the minimum amount of antimicrobial preservative required for preservative activity in the product composition is less than if the antimicrobial preservative were used alone.

[0016] In another embodiment, the antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) described herein. DETAILED DESCRIPTION OF THE INVENTION

[0017] The ether compounds of the present disclosure have the formula (I):

[0018] [ka]

[0019] [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; R3 is -OH, -R6-OH, -O-R7 or -R8-O-R9; R4 is -C2-C5 alkenyl (e.g., C2-C3 alkenyl), R5 is H, -C1-C5 alkyl (e.g., C1-C3 alkyl), or -C2-C5 alkenyl (e.g., C2-C3 alkenyl). is a compound of

[0020] With respect to the oxygen-containing groups 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).

[0021] Preferably, at least one of R1, R2, or R3 contains an -OH group. For example, at least one of R1, R2, or R3 may contain an -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 -OH groups. In such embodiments, the other R1, R2, or R3 may, but need not, contain an -OH group or an ether group. In further embodiments, R1, R2, and R3 each contain an -OH group.

[0022] In other embodiments, at least one of R1, R2, or R3 contains an -OH group, and the remaining two each contain an ether group.

[0023] References to R1, R2, and / or R3 containing an "-OH group" or an "ether group" should be understood to refer to the respective groups described herein from which R1, R2, and R3 are selected, where applicable, that contain the specified functional group (i.e., hydroxyl- or ether-containing). For example, when R3 is referred to as containing an -OH group, this indicates that R3 is -OH or -R6-OH. As a further example, when R3 is referred to as containing an ether group, this indicates that R3 is -O-R7 or -R8-O-R9. The same principles apply herein to the extent that R1, R2, and / or R3 are referred to as having an oxygen-containing group or functional group.

[0024] In general, the total number of carbons in R1, R2, and R3 combined is typically 12 or less, e.g., 8 or less or 6 or less. For example, in many embodiments, the total number of carbons in R1, R2, and R3 combined is in the range of 1 to 12, e.g., 2 to 12, 3 to 12, or 4 to 12, often 1 to 8, 2 to 8, 3 to 8, 4 to 8, 1 to 6, 2 to 6, or 3 to 6.

[0025] In general, the total number of carbons in R8 and R9 combined is typically 6 or less, or in many embodiments 4 or less.

[0026] More than one ether compound of formula (I) may be present or used in the compositions and methods of the present disclosure.

[0027] Preferably, in formula (I), R1 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, and 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, and R6, R8, and R9 are as described herein.

[0028] Preferably, in formula (I), R2 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.

[0029] In formula (I), R3 is -OH, -R6-OH, -O-R7, or -R8-O-R9, where R6 through R9 are as described herein. Preferably, R2 and R3 are each independently selected to have an oxygen-containing functional group 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 through R9 are as described herein. R2 and R3 may, but are not necessarily, the same.

[0030] Preferably, R2 is -R6-OH and R3 is -OH or -R6-OH.

[0031] In other embodiments, at least one of R2 or R3 contains an -OH group, and the other contains an ether group. For example, R2 can be -R6-OH, and R3 can be -O-R7 or -R8-O-R9. In other embodiments, R2 and R3 are each independently -O-R7 or -R8-O-R9, and preferably, R1 is -R6-OH.

[0032] In embodiments where R2 and R3 are each -R6-OH, each -O-R7, or each -R8-O-R9, it should be understood that the R6-R9 groups may, but need not necessarily, be the same in each of R2 and R3, where applicable (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, and R6 for R2 may be different or the same as R6 for R3, e.g., R6 in each is the same or different -C1-C6 alkylene or -C1-C4 alkylene (e.g., selected from methylene and ethylene). In another example, in many embodiments, R2 and R3 are each independently -R8-O-R9, and R8 and R9 for R2 can be different or the same as for R3, e.g., R8 in each is the same or different -C1-C5 alkylene or -C1-C3 alkylene (e.g., selected 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, e.g., R2 is -R8-O-R9 and R3 is -R6-OH (further, e.g., 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 noted above, preferably at least one of R1, R2, or R3 contains an -OH group; thus, in embodiments where neither R2 nor R3 contain an -OH group, R1 is preferably -R6-OH.

[0033] It should be understood that the selections for R1 described herein may be selected with any combination of R2 and R3 described herein, preferably with at least one of R1, R2, or R3 containing an -OH group. The same applies to the selections for R2 in relation to R1 and R3 and the selections for R3 in relation to R1 and R2, preferably with at least one of R1, R2, or R3 containing an -OH group in each case. For example, in many embodiments, any combination of R2 and R3 is selected, preferably with at least one of R2 or R3 containing an -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 have an oxygen-containing functional group, preferably at least one (or both) of R2 or R3 contains an —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).

[0034] In formula (I), R1, R2, and R3 may each independently be selected to have an oxygen-containing functional group as described herein, and preferably, at least one of R1, R2, or R3 contains an —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 through R9 are as described herein, and preferably, at least one of R1, R2, or R3 contains an —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 can be the same or different, for example, R6 is the same or different -C1-C6 alkylene or -C1-C4 alkylene (e.g., selected from methylene and ethylene).

[0035] In formula (I), R4 contains a non-aromatic carbon-carbon double bond. More specifically, R4 is -C2-C5 alkenyl. Preferably, any combination of R1, R2, and R3 described herein is selected, and R4 is C2-C3 alkenyl, preferably C2 alkenyl.

[0036] In formula (I), R5 is H, -C1-C5 alkyl (e.g., C1-C3 alkyl), or -C2-C5 alkenyl (e.g., C2-C3 alkenyl). Preferably, any combination of R1-R4 described herein is selected, and R5 is H, particularly, for example, R4 is C2 alkenyl, meaning that R4, R5, and the carbon atoms to which they are each attached together form an allyl group. In these preferred embodiments, the ether compounds of formula (I) are considered to be allyl ether compounds. In other embodiments, R5 is a short-chain alkyl or alkenyl as described herein.

[0037] "Alkyl," "alkylene," "alkenyl," and "alkenylene" groups as used herein can be unbranched or branched, depending on the chain length selected.

[0038] Examples of ether compounds of 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).

[0039] The ether compounds of formula (I) may be synthesized according to known methods or may be obtained as commercially available compounds.

[0040] In a further aspect of the present disclosure, the ether compounds described herein have one or more properties selected from antioxidant properties, surfactant properties, moisturizing properties, and chelating properties, such as those properties described or demonstrated herein. Preferably, at least two of R1, R2, or R3 contain an -OH group, and the ether compound has at least chelating properties. Preferably, at least two of R1, R2, or R3 contain an -OH group, and the ether compound has at least antioxidant properties. More preferably, at least two of R1, R2, or R3 contain an -OH group, and the ether compound has at least antioxidant properties and chelating properties, or at least antioxidant properties, chelating properties, surfactant properties, or at least antioxidant properties, chelating properties, surfactant properties, and moisturizing properties. For example, in such embodiments, R2 can be -R6-OH, R3 can be -OH or -R6-OH, and R1 can be as described herein, preferably 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, for the antioxidant properties referred to above, the ether compounds of formula (I) exhibit a Trolox equivalent (μM) (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, wherein 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, for the chelating properties referred to above, the ether compounds of formula (I) exhibit an EDTA equivalent value (μM) (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, wherein the EDTA equivalent value is determined according to the assay procedure of the Cupric Ion Chelating Assay Kit (Cat# AOX-16) (Instruction Manual ZBM0125.00, July 2021).

[0041] Conventional and / or soft preservatives can be used as the antimicrobial preservative. The ether compounds of formula (I) can be used to reduce the number and / or amount of such antimicrobial preservatives normally required to achieve the desired preservative activity in personal care products, cosmetics, and home care products. Antimicrobial preservatives suitable for personal care products, cosmetics, and home care products are known in the art. Examples of such conventional 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-releasing agents (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.

[0042] Preferably, the antimicrobial preservative is an isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), alkylhydroxamic acid and / or a salt thereof (e.g., hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid, a salt thereof, a combination thereof, preferably caprylhydroxamic acid and / or a salt thereof), aromatic aldehyde (e.g., cinnamic aldehyde), alcohol (e.g., aromatic alcohols such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic alcohol, phenolic compounds such as hydroxyacetophenone, combinations thereof), 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), glyceryl ethers (e.g., ethylhexylglycerin, chlorphenesin), aromatic ethers (e.g., phenoxyethanol), pyrithiones (e.g., zinc pyrithione, sodium pyrithione), organic acids (e.g., benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid, 4-hydroxybenzoic acid, combinations thereof), salts and / or esters of organic acids (e.g., esters and / or salts of the above organic acids, including, for example, sodium, potassium, calcium, magnesium, or ammonium salts, such as sodium benzoate, potassium sorbate, and esters including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or phenyl esters, such as butyl benzoate), ethyl lauroyl arginate (LAE), or any combination of the foregoing.

[0043] For example, the antimicrobial preservative may be alkylhydroxamic acid and / or a salt thereof (preferably hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid and / or a salt thereof or a combination thereof, in particular caprylhydroxamic acid and / or a salt thereof), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, methylpropan ... diol, 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, salts and / or esters of the foregoing acids, zinc pyrithione, sodium pyrithione, or combinations thereof.

[0044] 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, pyrithione, ethyl lauroyl arginate (LAE), or a combination thereof.

[0045] In particular, the antimicrobial preservative may include 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, esters or salts of the foregoing organic acids (e.g., sodium benzoate, potassium sorbate, etc.), or combinations thereof. For example, the antimicrobial preservative may include phenoxyethanol, benzyl alcohol, benzoic acid, a salt of benzoic acid (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT, or combinations thereof.

[0046] More than one antimicrobial preservative may be present or used in the compositions and methods of the present disclosure.

[0047] The optimal amount of the ether compound and antimicrobial preservative of the present application can vary depending, for example, on the particular compound and preservative selected, the end use application, the desired level of preservation, the final product properties, etc. Generally, the ether compound is present in an amount effective to enhance (e.g., meet or even exceed industry standards for antimicrobial efficacy) the antimicrobial efficacy (e.g., enhance the desired preservative, antibacterial, and / or antifungal efficacy) of the antimicrobial preservative in a product composition, such as a personal care product, cosmetic, or home care composition, compared to an equivalent amount of an antimicrobial preservative without the ether compound. In addition, the amount of the ether compound can also be influenced by the desired multifunctional benefit, such as one or more of antioxidant properties, surfactant properties, moisturizing properties, and / or chelating properties, as described herein.

[0048] For example, preferably, in formula (I), at least two of R1, R2, or R3 contain an -OH group (e.g., R2 is -R6-OH, R3 is -OH or -R6-OH, and R1 is as described herein, preferably 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 ether compound in the product composition provides at least chelating properties to the product composition. Preferably, at least two of R1, R2, or R3 contain an -OH group (e.g., R2 is -R6-OH and R3 is -OH or -R6-OH, and R1 is as described herein, preferably 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 ether compound provides at least antioxidant properties to the product composition. More preferably, at least two of R1, R2, or R3 contain an -OH group (e.g., R2 is -R6-OH and R3 is -OH or -R6-OH, where R1 is as described herein, preferably 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 ether compound provides at least antioxidant and chelating properties to the product composition, or provides at least antioxidant, chelating, and surfactant properties to the production composition, or provides at least antioxidant, chelating, surfactant, and moisturizing properties to the product composition.Preferably, for the above-referenced antioxidant properties imparted to a product composition, the amount of the ether compound of formula (I), e.g., the exemplary amounts disclosed herein (e.g., from about 0.01% by weight, from about 0.05% by weight, more preferably from about 0.1% by weight, from about 0.3% by weight, or from about 0.5% by weight to about 5% by weight, preferably up to about 3% by weight, up to about 2% by weight, more preferably up to about 1.5% by weight, or up to about 1% by weight, based on the weight of the composition) can be used in the product composition to increase the Trolox equivalent value (μM) of the composition (i.e., μmol Trolox / L sample) by at least 10%, more preferably at least 15%, at least 20% or at least 25%, particularly at least 30%, at least 40% or at least 50% compared to the Trolox equivalent value (μM) of the composition in the absence of the ether compound of formula (I), and the Trolox equivalent value (μM) can be increased by at least 10%, more preferably at least 15%, at least 20% or at least 25%, particularly at least 30%, at least 40% or at least 50%. Determined according to the assay procedure of the Kit (Cat# AOX-14) (Instruction Manual ZBM0123.00, April 2021). Preferably, for the above-mentioned chelating properties to be imparted to the product composition, the amount of the ether compound of formula (I), for example, the exemplary amounts disclosed herein (e.g., from about 0.01% by weight, from about 0.05% by weight, more preferably from about 0.1% by weight, from about 0.3% by weight, or from about 0.5% by weight to about 5% by weight, preferably up to about 3% by weight, up to about 2% by weight, more preferably up to about 1.5% by weight, or up to about 1% by weight, based on the weight of the composition) can be used in the product composition to increase the EDTA equivalent value (μM) of the composition (i.e., μmol EDTA / L sample) by at least 10%, more preferably at least 15%, at least 20% or at least 25%, particularly at least 30%, at least 40% or at least 50% compared to the EDTA equivalent value (μM) of the composition in the absence of the ether compound of formula (I), and the μM EDTA equivalent value can be increased by at least 10%, more preferably at least 15%, at least 20% or at least 25%, particularly at least 30%, at least 40% or at least 50%. Determined according to the assay procedure of the Kit (Cat# AOX-16) (Instruction Manual ZBM0125.00, July 2021).

[0049] Generally, the weight ratio of the ether compound to the antimicrobial preservative can range from about 1:50 to about 50:1, for example, 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 can be used. The present application provides for the use of the ether compound and antimicrobial preservative disclosed by the present invention in product compositions, such as personal care products, cosmetics, and home care products. Generally, the ether compound and antimicrobial preservative can each be present in the product composition in an amount ranging from about 0.001% by weight, about 0.005% by weight, preferably from about 0.01% by weight, about 0.05% by weight, more preferably from about 0.1% by weight, about 0.3% by weight, or about 0.5% by weight to about 5% by weight, preferably about 3% by weight, about 2% by weight, more preferably about 1.5% by weight, or about 1% by weight, based on the weight of the product composition, subject to any combination of the aforementioned lower and upper limits and any range therebetween. Depending on the antimicrobial preservative, even lower amounts of the antimicrobial preservative can be used, for example, from about 0.0001% by weight or more, or from about 0.0005% by weight or more. In certain such embodiments, the antimicrobial preservative is an isothiazolinone, preferably CMIT, MIT, BIT, or a combination thereof. In embodiments in which such small amounts of antimicrobial preservative are used, the amount by weight of ether compound may be proportionally substantially higher relative to the amount by weight of antimicrobial preservative, e.g., the ratio of ether compound to antimicrobial preservative may be as high as 100:1, as high as 500:1, as high as 1000:1, as high as 5000:1, or even higher. In certain such embodiments, the antimicrobial preservative is an isothiazolinone, preferably CMIT, MIT, BIT, or a combination thereof.

[0050] Typically, the total amount of the ether compound and antimicrobial preservative ranges from about 0.05% by weight, more preferably from about 0.1% by weight, from about 0.3% by weight, or from about 0.5% to about 10% by weight, preferably from about 5% by weight, more preferably from about 3% by weight, to about 2% by weight, to about 1.5% by weight, or to about 1% by weight, based on the weight of the product composition, subject to any combination of the aforementioned lower and upper limits and any range therebetween. For example, the total amount may be from about 0.05 to about 7% by weight, e.g., from about 0.1 to about 5% by weight, from about 0.1 to about 4% by weight, from about 0.1% to about 3% by weight, or from about 0.1% to about 0.3% by weight, or from about 0.5% to about 3% by weight, to about 2% by weight, or to about 1% by weight, based on the weight of the product composition.

[0051] Typically, the ether compound and antimicrobial preservative are each present in the product composition in an amount not exceeding about 2% by weight, preferably not exceeding about 1.5% by weight or not exceeding about 1% by weight, based on the weight of the product composition. Often, each is present in an amount less than 1% by weight. Preferably, the combined amount of the ether compound and antimicrobial preservative is not more than about 3% by weight or not more than about 2% by weight, for example, in a range of about 1.5% by weight or less (e.g., about 0.1% by weight or about 0.3% to about 1.5% by weight), about 1.2% by weight or less (e.g., about 0.1% by weight or about 0.3% to about 1.2% by weight), or about 1% by weight or less (e.g., about 0.1% by weight or about 0.3% to about 1% by weight) based on the weight of the product composition.

[0052] The ether compound can be combined with or added to the product composition in any suitable manner: before, concurrently with, or after the addition of the antimicrobial preservative.

[0053] The ether compounds of the present disclosure can be incorporated into any number and variety of personal care products, cosmetics, and home care products, particularly aqueous-based formulations, both water-soluble and those using water as a carrier, such as emulsions (whether oil-in-water or water-in-oil). Examples include, without limitation, household products and detergents, fabric detergents, dishwashing detergents, cleansers, soaps, bubble baths, disinfectants, deodorants, hygiene compositions, baby care products, antibacterial soaps, hand sanitizers, deodorants, antiperspirants, dermatological compositions, skin conditioners, skin moisturizers, wrinkle treatments, sunscreens, tanning lotions, hair products, shampoos, shower gels, conditioners, shaving creams, and the like. Personal care products include, for example, products used for skin care, hair care, oral care, personal cleaning or hygiene, sunscreens, and other applications. Examples of personal care products include shampoos, conditioners, shower gels, liquid soaps, skin lotions, and liquids for all personal care wet wipe applications. Examples of cosmetics include face creams, make-up, make-up removers, mascara and wet wipes. Examples of home care products include dish washing detergents, laundry detergents, cleaning wipes and cleaning formulations.

[0054] The product composition may contain many different ingredients depending on the end use, i.e., one or more additional ingredients suitable for use in personal care, cosmetic, or home care product compositions. In one example, a personal care composition includes an antimicrobial preservative and an ether compound of Formula (I) described herein, and one or more additional ingredients suitable for use in personal care compositions. In another example, a cosmetic composition includes an antimicrobial preservative and an ether compound of Formula (I) described herein, and one or more additional ingredients suitable for use in cosmetic compositions. 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 uses. Examples of such products include, without limitation, skin toners, skin cleansers, night creams, skin creams, shaving creams, skin lotions, makeup products, mascara, lipstick, blush, gloss, eyeliner, makeup remover, sunscreen, lip balm, fragrance, massage oils, shampoos, conditioners, hair styling gels, hair repair products, hair tonics, hair fixatives, hair mousses, bath gels and shower gels, liquid soaps, moisturizing sprays, bath additives, eye preparations, foam type soaps and body washes, liquids for any personal care wet wipe application, and the like.

[0055] Depending on the application, personal care or cosmetic compositions can contain any of many different compatible ingredients, such as solvents, surfactants, emulsifiers, rheology modifiers, conditioning agents, emollients, skin care ingredients, moisturizers, thickeners, humectants, fillers, antioxidants, active ingredients, such as dermatological active ingredients, active ingredients typically adapted for topical application, fragrances, and the like, as well as various mixtures thereof.

[0056] In another example, a home care composition includes an antimicrobial preservative and an ether compound of Formula (I) described herein, as well as one or more additional ingredients suitable for use in a home care composition. Examples include dishwashing detergents, laundry detergents, cleaning wipes, cleaning formulations, and other home care applications. Depending on the application, the home care composition can contain, for example, detergents, emulsifiers, surfactants, thickeners, gelling agents, bleaches, whitening agents, deodorizers, enzymes, stabilizers, fragrances, and the like, as well as various mixtures thereof. Examples of the aforementioned ingredients and other agents used in personal care, cosmetic, and home care product compositions are known in the art.

[0057] The ether compounds of the present disclosure can be included in a variety of different product compositions, such as, 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 colors, hair tonics, hair gels, hair dressings, styling aids and other hair care preparations; shaving applications such as shaving creams, aftershave lotions and other shaving applications; personal cleaners for body and hands such as liquid bath soaps and detergents; fragrance preparations such as perfumes, after-bath splash products and other similar fragranced preparations; skin care products such as moisturizers, creams and lotions and other similar skin care products; makeup products such as mascara, base foundations and the like; makeup remover products, sunscreen products, indoor tanning products and other similar personal care products; wipes used in personal cleaning and hygiene applications such as newborn wipes, wet toilet wipes, makeup remover wipes and exfoliating wipes or formulations used for soaking home care wet wipe formulations and the like.

[0058] Typically, product compositions have a pH in the range of about 3.0, about 4.0, about 5.0, about 5.5, or about 6.0 to about 11, e.g., about 3.0 to about 10, about 4.0 to about 8.5, or about 5.0 to about 7.5. Unless otherwise specified, pH values ​​or ranges refer to the pH at room temperature (20-25°C). The selected pH will vary depending, for example, on the particular end use application. For example, personal care or cosmetic compositions preferably have a pH in the range of about 3.0, or about 4.0 to about 8.0, e.g., about 4.0, or about 5.0 to about 7.5, or about 7.0. The home care composition preferably has a pH ranging from about 3.0 to about 11, e.g., 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.

[0059] 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).

[0060] The present disclosure is not limited to any particular technique for preparing the product composition, and the antimicrobial preservative and the ether compound of Formula (I) can be added to the product composition in any suitable manner. For example, the antimicrobial preservative and the ether compound of Formula (I) can be applied to the product formulation as a mixture, or can be applied to the formulation individually, simultaneously, or in any order.

[0061] In a further aspect, the present disclosure provides the use of an ether compound of formula (I) as described herein to enhance the antimicrobial efficacy of an antimicrobial preservative in a personal care product, cosmetic or home care product composition.

[0062] In another aspect, there is provided a method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care product, cosmetic, or home care product composition, comprising combining or mixing the antimicrobial preservative with an ether compound of Formula (I) described herein, wherein the enhanced antimicrobial efficacy is compared to an equivalent amount of the antimicrobial preservative without the ether compound.

[0063] In a further aspect, there is provided a method of reducing the minimum amount of antimicrobial preservative required for preservative activity in a personal care product, cosmetic or home care product composition, comprising the step of combining or mixing an antimicrobial preservative with an ether compound of Formula (I) described herein, wherein after said step of combining or mixing with the ether compound, the minimum amount of antimicrobial preservative required for preservative activity in the product composition is less than if the antimicrobial preservative were used alone.

[0064] It is understood that the descriptions herein regarding the ether compounds of formula (I), antimicrobial preservatives, exemplary ratios and amounts, product compositions and ingredients, etc. also apply to the methods of the present disclosure.

[0065] A variety of different microorganisms can be controlled in accordance with the present disclosure. For example, the combination of an antimicrobial preservative and an 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, Burkholderia cepacia, Pseudomonas putida, Candida albicans, Aspergillus brasiliensis, and mixtures thereof. As known in the art, antimicrobial activity can be demonstrated in a variety of suitable antimicrobial efficacy tests. Preferably, when added to a product composition, the antimicrobial preservative and the ether compound of formula (I) provide antimicrobial activity according to the challenge test procedure in the Examples below, and achieve a passing growth rating according to the criteria associated with Table 7 and its accompanying description herein.

[0066] In a further aspect of the present disclosure, the antimicrobial composition comprises an antimicrobial preservative and an ether compound of Formula (I) described herein, preferably the antimicrobial preservative and the ether compound of Formula (I) collectively constitute 50 to 100% by weight of the active ingredients in the antimicrobial composition, more preferably the antimicrobial preservative is an isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), alkylhydroxamic acid and / or a salt thereof (e.g., hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid, a salt thereof, combinations thereof, preferably caprylhydroxamic acid and / or a salt thereof), aromatic aldehyde (e.g., cinnamic aldehyde), alcohol (e.g., aromatic alcohols such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic alcohol, phenolic compounds such as hydroxyacetophenone, combinations thereof), diol (e.g., bronopol, glycols such as 1,2-propanediol, 1,3-butanediol, ethanol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., caprylyl glycol), and combinations thereof), glyceryl ethers (e.g., ethylhexylglycerin, chlorphenesin), aromatic ethers (e.g., phenoxyethanol), pyrithiones (e.g., zinc pyrithione, sodium pyrithione), organic acids (e.g., benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hexa-2,4-dienoic acid , 4-hydroxybenzoic acid, combinations thereof), salts and / or esters of organic acids (e.g., esters and / or salts of the above organic acids, such as sodium, potassium, calcium, magnesium, or ammonium salts, including, for example, sodium benzoate, potassium sorbate, etc., and esters including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or phenyl esters, including, for example, butyl benzoate, etc.), ethyl lauroyl arginate (LAE), or combinations thereof.

[0067] For example, the antimicrobial preservative may be alkylhydroxamic acid and / or a salt thereof (preferably hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid and / or a salt thereof or a combination thereof, in particular caprylhydroxamic acid and / or a salt thereof), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, methyl ... The composition may include ethanol, 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, salts and / or esters of the foregoing acids, zinc pyrithione, sodium pyrithione, or combinations thereof.

[0068] 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, pyrithione, ethyl lauroyl arginate (LAE), or a combination thereof.

[0069] In particular, the antimicrobial preservative can include 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, esters or salts of the foregoing organic acids (e.g., sodium benzoate, potassium sorbate, etc.), or combinations thereof. For example, the antimicrobial preservative can include phenoxyethanol, benzyl alcohol, benzoic acid, salts of benzoic acid (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT, or combinations thereof.

[0070] Typically, the antimicrobial composition comprises the antimicrobial preservative and the ether compound of Formula (I) in a combined amount that represents a majority (>50% by weight) of the active ingredients in the antimicrobial composition, e.g., at least 60% or at least 70% by weight, preferably at least 80% by weight, more preferably at least 85% by weight, at least 90% by weight, at least 95% by weight, at least 96% by weight, at least 97% by weight, at least 98% by weight, or at least 99% by weight, based on the total weight of the active ingredients in the antimicrobial composition. The antimicrobial composition often contains from about 60-100% by weight, preferably from about 65-100% by weight, from about 70-100% by weight, from about 75-100% by weight, from about 80-100% by weight, from about 85-100% by weight, from about 90-100% by weight, or from about 95% by weight to about 100% by weight of the combination of the antimicrobial preservative and the ether compound of Formula (I), based on the total weight of the active ingredients in the antimicrobial composition. In many embodiments, the antimicrobial composition comprises active ingredients consisting essentially of, or in further embodiments consisting of, an antimicrobial preservative and an ether compound of formula (I).

[0071] Preferably, the antimicrobial composition comprises the antimicrobial preservative and the ether compound of Formula (I) in a combined amount of 50-100% by weight of the total weight of the antimicrobial composition, and typically comprises a majority (>50% by weight) of the antimicrobial composition, e.g., at least 60% or at least 70% by weight, preferably at least 80% by weight, more preferably at least 85% by weight, at least 90% by weight, at least 95% by weight, at least 96% by weight, at least 97% by weight, at least 98% by weight, or at least 99% by weight. The antimicrobial composition often contains about 60-100% by weight, preferably about 70-100% by weight, about 75-100% by weight, about 80-100% by weight, about 85-100% by weight, about 90-100% by weight, or about 95 to about 97 to about 100% by weight of the combination of the antimicrobial preservative and the ether compound of Formula (I), 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).

[0072] The antimicrobial composition may, but need not, include one or more added solvents or carriers. When present, the solvent or carrier typically comprises from about 10%, about 20%, or about 30% to about 90%, about 85%, about 80%, about 70%, about 60%, or about 50% by weight, based on the total weight of the antimicrobial composition. Solvents or carriers can be selected according to their compatibility or applicability with the desired end use or final product formulation, such as personal care products, cosmetics, or home care compositions (e.g., cosmetically acceptable solvents or carriers). 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.

[0073] The antimicrobial composition may, but need not, contain one or more excipients, typically in trace amounts. Excipients can likewise be selected according to their compatibility or applicability to the desired end use or final product formulation, such as a personal care product, cosmetic, or home care composition (e.g., cosmetically acceptable excipients). Examples of excipients include, but are not limited to, dispersants, solubilizers, buffers, and / or stabilizers. The antimicrobial composition can, for example, contain 0 to about 10% by weight of one or more excipients, e.g., from about 0.001% by weight, from about 0.01% by weight, from about 0.05% by weight, or from about 0.1% by weight to about 5% by weight, to about 3% by weight, or to about 1% by weight, based on the total weight of the antimicrobial composition. For example, the amount of excipient can be in the range of 0 to about 5% by mass, 0 to about 3% by mass, about 0.01 to about 5% by mass, about 0.1 to about 5% by mass, about 0.01 to about 3% by mass, about 0.1 to about 3% by mass, about 0.01 to about 1% by mass, or about 0.1 to about 1% by mass.

[0074] Typically, the antimicrobial composition comprises a total amount of about 10 to 100% by weight of the antimicrobial preservative and the ether compound of Formula (I), e.g., from about 15% by weight, or from about 20% by weight, from about 30% by weight, from about 40% by weight, from about 50% by weight, or from about 60% by weight to 100% by weight, to about 99% by weight, to about 97% by weight, to about 95% by weight, to about 90% by weight, to about 80% by weight, or to about 70% by weight, based on the total weight of the antimicrobial composition, optionally with one or more solvents or carriers in an amount of from 0 to about 9% by weight, based on the total weight of the antimicrobial composition. 0% by weight, e.g., from about 10% by weight, from about 20% by weight, or from about 30% by weight to about 90% by weight, to about 85% by weight, to about 80% by weight, to about 70% by weight, to about 60% by weight, to about 50% by weight, or to about 40% by weight, and optionally one or more excipients in an amount of about 0 to about 10% by weight, e.g., from about 0.001% by weight, from about 0.01% by weight, from about 0.05% by weight, or from about 0.1% by weight to about 5% by weight, to about 3% by weight, or to about 1% by weight, based on the total weight of the antimicrobial composition. For example, the total amount of the antimicrobial preservative and the ether compound of Formula (I) may be about 10% to about 90% by weight, about 20% to about 80% by weight, or about 30% to about 70% by weight, and the amount of the solvent or carrier may be about 10% to about 90% by weight, about 20% to about 80% by weight, or about 30% to about 70% by weight, optionally further including one or more excipients.

[0075] In many embodiments, the antimicrobial composition consists essentially of an antimicrobial preservative, an ether compound of Formula (I), optionally one or more solvents or carriers, and optionally one or more excipients, 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.

[0076] The antimicrobial composition can be added to the product composition in an amount effective to achieve a desired level of antimicrobial effectiveness in the product composition or preservation of the product composition. It should be understood that the descriptions herein regarding the ether compounds of formula (I), antimicrobial preservatives, exemplary ratios and amounts, product compositions and ingredients, etc. also apply to the antimicrobial compositions of the present disclosure and / or their addition to product compositions, particularly personal care, cosmetic, or home care product compositions.

[0077] The present disclosure further includes, without limitation, the following exemplary embodiments.

[0078] Embodiment 1: Antimicrobial preservative and a composition of formula (I)

[0079] [ka]

[0080] [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; R3 is -OH, -R6-OH, -O-R7 or -R8-O-R9; R4 is -C2-C5 alkenyl; 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 to C5 alkylene or -C3 to C5 alkenylene; R9 is -C1-C5 alkyl or -C3-C5 alkenyl. An antibacterial composition comprising an ether compound of the formula:

[0081] Embodiment 2: A product composition comprising an ether compound of formula (I) as described in embodiment 1 and an antimicrobial preservative, wherein the product composition is selected from personal care products, cosmetics, and home care products.

[0082] Embodiment 3: A method of providing antimicrobial activity to a product composition, comprising adding to the product composition an antimicrobial preservative and an ether compound of Formula (I) as described in embodiment 1, wherein the product composition is selected from personal care products, cosmetics, and home care products.

[0083] Embodiment 4: A method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, comprising adding to the product composition an ether compound of formula (I) as described in embodiment 1, wherein the product composition is selected from personal care products, cosmetics, and home care products.

[0084] 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 of embodiment 1, wherein the product composition is selected from personal care products, cosmetics, and home care products.

[0085] Embodiment 6: Use of an ether compound of formula (I) as described in embodiment 1 to enhance the antimicrobial effect of an antimicrobial preservative in a product composition, wherein the product composition is selected from personal care products, cosmetics, and home care products.

[0086] Embodiment 7: The antimicrobial composition, product composition, method or use of any one of embodiments 1 to 6, wherein at least one of R1, R2 or R3 contains an —OH group.

[0087] Embodiment 8: The antibacterial composition, product composition, method or use of any one of embodiments 1 to 7, wherein at least one of R1, R2 or R3 contains an —OH group and at least one other of R1, R2 or R3 contains an ether group.

[0088] Embodiment 9: The antimicrobial composition, product composition, method or use of any one of embodiments 1 to 8, wherein at least two of R1, R2, or R3 contain an —OH group.

[0089] Embodiment 10: The antimicrobial composition, product composition, method or use of any one of embodiments 1 to 7, wherein R1, R2, and R3 each contain an —OH group.

[0090] Embodiment 11: The antibacterial composition, product composition, method or use of any one of embodiments 1 to 10, wherein the total number of carbons in R1, R2, and R3 combined is 12 or less, preferably 8 or less or 6 or less.

[0091] Embodiment 12: An antibacterial composition, product composition, method or use according to any one of embodiments 1 to 11, wherein in formula (I), R1 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.

[0092] Embodiment 13: The antibacterial composition, product composition, method or use of any one of embodiments 1 to 9, 11 and 12, wherein in formula (I), R2 is -C1-C4 alkyl or -C2-C4 alkenyl.

[0093] Embodiment 14: An antibacterial composition, product composition, method or use according to any one of embodiments 1 to 12, wherein in formula (I), R2 is R6-OH, -O-R7, or -R8-O-R9.

[0094] Embodiment 15: An antibacterial composition, product composition, method or use according to any one of embodiments 1 to 12 and 14, wherein R2 is R6-OH and R3 is -OH or -R6-OH.

[0095] Embodiment 16: The antibacterial composition, product composition, method or use of any one of embodiments 1 to 9, 11, 12 and 14, wherein R2 is -O-R7 or -R8-O-R9, and R3 is -OH or -R6-OH, preferably R2 is -R8-O-R9, and more preferably R1 is H, -R6-OH, -C1-C4 alkyl or -C2-C4 alkenyl, or R1 is H, -R6-OH or -C1-C4 alkyl.

[0096] Embodiment 17: The antibacterial composition, product composition, method or use according to any one of embodiments 1 to 16, wherein in formula (I), R4 is C2-C3 alkenyl, preferably C2 alkenyl.

[0097] Embodiment 18: The antibacterial composition, product composition, method or use of any one of embodiments 1 to 17, wherein in formula (I) R5 is H.

[0098] Embodiment 19: The antibacterial composition, product composition, method or use according to any one of embodiments 1 to 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 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.

[0099] Embodiment 20: The ether compound of formula (I) is 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 combinations thereof 7. The antimicrobial composition, product composition, method or use according to any one of embodiments 1 to 6, selected from:

[0100] Embodiment 21: The antimicrobial composition, product composition, method or use of any one of embodiments 1 to 20, wherein the ratio of antimicrobial preservative to 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.

[0101] Embodiment 22: The antimicrobial composition of any one of embodiments 1 to 21, comprising at least about 50% by weight of a combination of an antimicrobial preservative and an ether compound of Formula (I), based on the total weight of the active ingredients in the antimicrobial composition, preferably about 60-100%, about 70-100%, about 75-100%, about 80-100%, about 85-100%, about 90-100%, or about 95 to about 97-100% by weight, based on the total weight of the active ingredients in the antimicrobial composition.

[0102] Embodiment 23: An antimicrobial composition according to any one of embodiments 1 to 22, comprising active ingredients consisting essentially of, or in a further embodiment, of, an antimicrobial preservative and an ether compound of Formula (I).

[0103] Embodiment 24: An antimicrobial composition according to any one of embodiments 1 to 23, comprising at least about 50% by weight of a combination of an antimicrobial preservative and an ether compound of formula (I), based on the total weight of the antimicrobial composition, preferably about 60-100%, about 70-100%, about 75-100%, about 80-100%, about 85-100%, about 90-100%, or from about 95% by weight, or from about 97% to 100% by weight, based on the total weight of the composition.

[0104] Embodiment 25: The antimicrobial composition of any one of embodiments 1 to 24, consisting essentially of, or in a further embodiment, consisting of, an antimicrobial preservative and an ether compound of Formula (I).

[0105] Embodiment 26: The antimicrobial preservative is selected from the group consisting of isothiazolinones (e.g., CMIT, MIT, BIT, combinations thereof), alkylhydroxamic acids and / or salts thereof (e.g., hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid, salts thereof, combinations thereof, preferably caprylhydroxamic acid and / or salts thereof), aromatic aldehydes (e.g., cinnamic aldehyde), alcohols (e.g., aromatic alcohols such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic alcohol, phenolic compounds such as hydroxyacetophenone, combinations thereof), diols (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), 26. The antimicrobial composition, product composition, method, or use of any one of embodiments 1-25, comprising an organic acid (e.g., a combination 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, or a combination thereof), a salt and / or ester of an organic acid (e.g., an ester and / or salt of the above organic acids, such as sodium, potassium, calcium, magnesium, or ammonium salts, including, for example, sodium benzoate, potassium sorbate, and the like, and esters including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or phenyl esters, butyl benzoate, and the like), ethyl lauroyl arginate (LAE), or a combination thereof.

[0106] Embodiment 27: The antimicrobial preservative is selected from the group consisting of 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), an organic 26. The antimicrobial composition, product composition, method or use of any one of embodiments 1 to 25, comprising an acid salt or ester (e.g., an ester and / or salt of the organic acids described above, e.g., sodium, potassium, calcium, magnesium or ammonium salts, e.g., including sodium benzoate, potassium sorbate, etc., and esters including methyl, ethyl, propyl, isopropyl, butyl, isobutyl or phenyl esters, e.g., butyl benzoate, etc.), pyrithione (e.g., zinc pyrithione, sodium pyrithione), ethyl lauroyl arginate (LAE), or a combination thereof.

[0107] Embodiment 28: The antimicrobial preservative is selected from the group consisting of alkylhydroxamic acid and / or salts thereof (preferably hexanohydroxamic acid, caprylhydroxamic acid, decanohydroxamic acid, laurohydroxamic acid and / or salts thereof or combinations thereof, in particular caprylhydroxamic acid and / or salts thereof), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamic aldehyde, cinnamic alcohol, 1,2-propanediol, 1,3-butanediol, 1,2-pentanediol, 26. The antimicrobial composition, product composition, method or use of any one of embodiments 1 to 25, comprising: 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, salts and / or esters of the foregoing acids, zinc pyrithione, sodium pyrithione, or combinations thereof.

[0108] Embodiment 29: The antimicrobial composition, product composition, method, or use of 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, esters or salts of said organic acids (e.g., sodium benzoate, potassium sorbate, etc.), or combinations thereof; or wherein 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 combinations thereof.

[0109] Embodiment 30: The product composition, method, or use of any one of embodiments 2 to 21 and 26 to 29, wherein the ether compound of formula (I) is present in the product composition in an amount ranging from about 0.05% by weight, preferably from about 0.1% by weight, from about 0.3% by weight, or from about 0.5% to about 10% by weight, preferably up to about 5% by weight, more preferably up to about 3% by weight, up to about 2% by weight, particularly up to about 1.5% by weight, or up to about 1% by weight, based on the total weight of the product composition.

[0110] Embodiment 31: The product composition, method, or use of any one of embodiments 2 to 21 and 26 to 30, wherein the ether compound of formula (I) and the antimicrobial preservative are present in the product composition in an amount ranging from about 0.05% by weight, preferably from about 0.1% by weight, from about 0.3% by weight, or from about 0.5% by weight to about 5% by weight, preferably up to about 3% by weight, up to about 2% by weight, more preferably up to about 1.5% by weight, or up to about 1% by weight, based on the total weight of the product composition.

[0111] Embodiment 32: The product composition, method, or use of any one of embodiments 2 to 21 and 26 to 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% by weight, from about 0.3% by weight, or from about 0.5% by weight to about 10% by weight, preferably up to about 5% by weight, more preferably up to about 3% by weight, up to about 2% by weight, up to about 1.5% by weight, or up to about 1% by weight, based on the weight of the product composition.

[0112] Embodiment 33: The product composition, method, or use of any one of embodiments 2 to 21 and 26 to 32, wherein the ether compound of formula (I) and the antimicrobial preservative are each present in the product composition in an amount not exceeding 2% by weight, preferably not exceeding 1.5% by weight, or not exceeding 1% by weight, based on the weight of the product composition.

[0113] Embodiment 34: The product composition, method or use of any one of embodiments 2 to 21 and 26 to 33, wherein the combined amount of the ether compound of formula (I) and the antimicrobial preservative does not exceed 3% by weight, preferably does not exceed 2% by weight, based on the weight of the product composition, for example, from about 1.5% by weight or less (e.g., from about 0.1% by weight, or from about 0.3% to about 1.5% by weight), from about 1.2% by weight or less (e.g., from about 0.1% by weight, or from about 0.3% to about 1.2% by weight), or from about 1% by weight or less (e.g., from about 0.1% by weight, or from about 0.3% to about 1% by weight).

[0114] Embodiment 35: The antimicrobial composition, product composition, method, or use of any one of embodiments 1 to 34, wherein the ether compound of formula (I) has one or more properties selected from antioxidant properties, surfactant properties, moisturizing properties, and chelating properties.

[0115] Embodiment 36: In the formula (I), at least two of R1, R2 or R3 contain an -OH group (e.g., R2 is -R6-OH and R3 is -OH or -R6-OH, preferably R1 is H, -R6-OH, alkyl or alkenyl, or H, -R6-OH or -C1-C6 alkyl or -C1-C4 alkyl (e.g., methyl or ethyl)), the ether compound of formula (I) has at least antioxidant properties, at least chelating properties, or at least antioxidant and chelating properties, the antioxidant properties being in a Trolox equivalent (TE) value (μM) (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 properties being in a EDTA equivalent value (μM) (i.e., μmol Trolox / L sample), EDTA / L sample), at least 50 μM EDTA equivalent, more preferably at least 75 μM EDTA equivalent or at least 100 μM EDTA equivalent, in particular at least 150 μM EDTA equivalent, at least 175 μM EDTA equivalent or at least 200 μM EDTA equivalent, the Trolox equivalent value being 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 equivalent value being determined according to the assay procedure of the Cupric Ion Chelating Assay Kit (Cat# AOX-16) (Instruction Manual ZBM0125.00, July 2021), preferably wherein in formula (I), R4 is C2-C3 alkenyl (particularly C2 alkenyl), and more preferably wherein in formula (I), R5 is H.

[0116] Embodiment 37: In formula (I), at least two of R1, R2, or R3 contain an -OH group (e.g., R2 is -R6-OH and R3 is -OH or -R6-OH, preferably R1 is H, -R6-OH, alkyl, or alkenyl, or H, -R6-OH, or -C1-C6 alkyl, or -C1-C4 alkyl (e.g., methyl or ethyl)), and the amount of ether compound of formula (I) (e.g., the amount according to any one or combination of embodiments 30 to 34) is at least antioxidant properties, at least chelating properties, or at least The ether compound of formula (I) also provides antioxidant and chelating properties to the product composition, the antioxidant properties provided to the product composition increasing the Trolox equivalent value (μM) of the composition (i.e., μmol Trolox / L sample) by at least 10%, more preferably at least 15%, at least 20% or at least 25%, particularly at least 30%, at least 40% or at least 50% compared to the Trolox equivalent value (μM) of the composition in the absence of the ether compound of formula (I), and the chelating properties provided to the product composition increasing the EDTA equivalent value (μM) of the composition (i.e., μmol Trolox / L sample) by at least 10%, more preferably at least 15%, at least 20% or at least 25%, particularly at least 30%, at least 40% or at least 50% compared to the Trolox equivalent value (μM) of the composition in the absence of the ether compound of formula (I). The Trolox equivalent value (μM) 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 EDTA equivalent value (μM) of the product composition is increased by at least 10%, more preferably at least 15%, at least 20%, or at least 25%, particularly at least 30%, at least 40%, or at least 50%, compared to the EDTA equivalent value (μM) of the composition in the absence of the ether compound of formula (I). The Trolox equivalent value (μM) 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 EDTA equivalent value (μM) 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 in formula (I), R4 is C2-C3 alkenyl (particularly C2 alkenyl), and more preferably wherein in formula (I), R5 is H.

[0117] Embodiment 38: The product composition, method, or use of any one of embodiments 2 to 21 and 26 to 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.

[0118] Embodiment 39: The product composition, method, or use of any one of embodiments 2 to 21 and 26 to 38, wherein the product composition is a personal care product or cosmetic selected from a shampoo, a conditioner, a shower gel, a liquid soap, a skin lotion, a liquid wet wipe, a face cream, a hair treatment, a makeup product, and a makeup remover.

[0119] Unless otherwise specified, the following terms are defined as follows:

[0120] As used herein, the articles "a," "an," and "the" preceding an element or component of the invention are intended to be open-ended regarding the number of instances (i.e., occurrences) of the element or component. Thus, "a," "an," and "the" should be read to include one or at least one, and singular word forms of elements or components also include plurals unless the number is clearly intended to be singular.

[0121] As used herein, the term "alkyl" means a monovalent straight or branched saturated hydrocarbon having the specified number of carbons.

[0122] As used herein, the term "alkylene" means a divalent straight or branched chain saturated hydrocarbon having the specified number of carbons.

[0123] As used herein, the term "alkenyl" means a monovalent straight or branched chain hydrocarbon having at least one carbon-carbon double bond.

[0124] As used herein, the term "alkenylene" means a divalent straight or branched chain hydrocarbon having at least one carbon-carbon double bond.

[0125] As used herein, the term "comprising" means the presence of stated features, integers, steps, or components as recited in a claim, but does not exclude 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.

[0126] As used herein, the term "about" modifying the amount of a component or reactant utilized refers to variations in the numerical amount that may occur, for example, through typical measuring and liquid handling procedures used to make concentrates or use solutions in practical environments, through inadvertent errors in these procedures, through differences in the manufacture, source, or purity of the components utilized to produce the composition or carry out the method.

[0127] Where present, all ranges are inclusive and combinable. For example, if a range of "1 to 5" is listed, the listed range should be interpreted as including ranges such as "1 to 4," "1 to 3," "1 to 2," "1 to 2 & 4 to 5," "1 to 3 & 5," etc.

[0128] When a parameter is given as a range, as a preferred range, or as a list of upper and lower preferred values, it is understood that all ranges formed from any pairing of any upper range value or preferred value with any range lower limit or preferred value are specifically disclosed, regardless of whether the ranges are separately disclosed. When a range of numerical values ​​is recited herein, unless otherwise stated, the range is intended to include both endpoints, 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 recited in the specification. [Example]

[0129] The following examples demonstrate that the ether compounds of the present disclosure, when incorporated into various product formulations, surprisingly improved the preservative effectiveness of conventional 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 wide range of different bacteria and fungi, thereby enabling a reduction in the level of conventional or soft preservative needed to protect such products from microbial growth. The ether compounds of the present disclosure further surprisingly (i) exhibited significant antioxidant properties based on determined Trolox equivalent values, imparting antioxidant properties to the product compositions, (ii) exhibited moisturizing properties comparable to known moisturizing ingredients such as ethylhexylglycerin, as demonstrated by a reduction in water activity (measured with a Rotronic water activity meter), (iii) exhibited a reduction in surface tension after metering into water, demonstrating surfactant properties, and (iv) exhibited significant chelating properties based on determined EDTA equivalent values. Representative ether compounds disclosed by the present invention and compounds used in the following experimental examples are shown in Table 1.

[0130] [Table 1]

[0131] Example 1 Challenge studies demonstrating enhanced preservative properties of traditional soft preservatives A modification of the Personal Care Products Council (PCPC) protocol was used to evaluate the preservative activity of representative rinse-off and leave-on product compositions (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, pp. 101-109).

[0132] The evaluation was conducted at 25°C using a 4-week, two-cycle microbial preservative effectiveness test (challenge test) to determine the preservative effectiveness of each treatment. The ether compounds disclosed in this invention were tested alone and in combination with certain antimicrobial preservatives in various product formulations. The compounds were metered into different compositions, including a lotion containing carbomer (leave-on, Table 2), a serum composition containing xanthan gum (leave-on, Table 3), a body wash formulation (rinse-off, Table 4), and a cream formulation (leave-on, Table 5), and mixed thoroughly at room temperature.

[0133] Table 2 shows an exemplary composition for a carbomer-based anionic lotion composition. Carbomer is commonly used as a synthetic rheology modifier in personal care products. The following compositions were made by separately heating the aqueous phase (A) and the oil phase (B) to 75-80°C. The oil phase was then poured into the aqueous phase and mixed with an overhead mixer and homogenizer. The oil-in-water emulsion was cooled to room temperature. The pH was adjusted to 6.0-6.5 using triethanolamine.

[0134] [Table 2]

[0135] Table 3 shows an exemplary xanthan gum-based serum. The serum composition was made by adding all ingredients to a beaker, mixing with an overhead mixer, and heating to 75-80°C. The mixture was homogenized and cooled to room temperature. The pH was adjusted to pH 5.0-5.5 with sodium hydroxide solution.

[0136] [Table 3]

[0137] Table 4 shows a typical body wash formulation. The composition was made by mixing ACULYN 88 and water in a beaker, then adding STEOL 230 and AMPHOSOL CA. The solution was mixed in an overhead mixer. The final pH was adjusted to 6.8 using triethanolamine.

[0138] [Table 4]

[0139] Table 5 shows a representative nonionic cream formulation. The following composition was made by separately heating the water phase (A) and oil phase (B) to 75-80°C. The oil phase was then poured into the water phase and mixed with an overhead mixer and homogenizer. The oil-in-water emulsion was cooled to room temperature. SEPIGEL 305 was then added to the emulsion. The final pH was adjusted to 5.0 using sodium hydroxide solution.

[0140] [Table 5]

[0141] After dispensing, the sample was divided into two separate aliquots of 5 grams each. One aliquot was inoculated with 50 μl of the diluted bacterial pool and the second aliquot was inoculated with 50 μL of the diluted fungal pool described below. A product sample without preservative was included in the test as a growth control.

[0142] A mixed bacterial inoculum was prepared using 24-hour cultures of test bacteria (Table 6) grown in trypticase soy broth (TSB). Equal volumes of the bacterial test strains were combined and diluted 1:10 in phosphate buffer to give approximately 5 x 10 per mL. 7 ~5×10 8 An inoculum of 100 colony-forming units (cfu / mL) was obtained. Test samples were inoculated with 1% of the mixed bacterial inoculum. A mixed fungal inoculum was prepared using a cell suspension of the yeast Candida albicans ATCC#10231 and the mold Spergillus brasiliensis ATCC#16404 in phosphate buffer. Equal amounts of the fungal test strains were combined and diluted 1:10 with phosphate buffer to obtain approximately 5 x 10 6 ~5×10 7 cfu / mL inoculum was obtained. Test samples were inoculated with 1% of the mixed fungal inoculum.

[0143] [Table 6]

[0144] Samples were challenged with a microorganism at time zero and a second inoculation 7 days later. The number of microorganisms spiked into each sample was determined by 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 4-week test period. Samples were monitored for bacterial and fungal contamination after 2, 7, 14, 21, and 28 days. Bacterial-challenged samples were streak-plated onto trypticase soy agar (TSA) and incubated at 30°C for 24 hours. Fungal-challenged samples were streak-plated onto potato dextrose agar (PDA) and incubated at 25°C for 7 days. After incubation, plates were evaluated for growth to determine the colony-forming units per gram (CFU / g) present in each test sample at each test time point. Table 7 presents the growth scores. All ratings of excellent, good, and fair were considered to have passed the challenge test. As used in various challenge test methods, the pass criteria were more stringent for bacteria than for fungi. A rating of 2, 3, or 4 at 21 and / or 28 days was considered a fail for bacteria. For fungi, a rating of 2 at 21 and / or 28 days was considered a pass.

[0145] [Table 7]

[0146] For the bacterial challenge test, if the composition had a bacterial growth rating score of 1 or less on days 21-28 of the test period, the composition was scored as "pass," and if the composition had a bacterial growth rating score of 2 or greater on days 21-28 of the test period, the composition was scored as "fail."

[0147] For the fungal challenge test, if the composition had a fungal growth assessment score of 2 or less on days 21-28 of the test period, the composition was scored as "pass," and if the composition had a fungal growth assessment score of greater than 2 on days 21-28 of the test period, the composition was scored as "fail."

[0148] A "pass" rating for the dispensed composition was contingent on the sample containing no preservative having a "fail" rating.

[0149] Example 1A Representative leave-on lotion formulations were prepared according to Table 2. As shown in Table 8, when phenoxyethanol (POE), benzyl alcohol (BA), or a compound from Table 1 was dispensed alone, none of the lotion formulations passed the challenge test. However, when phenoxyethanol or benzyl alcohol was dispensed with a combination of each of Compounds 1-4, the lotion formulations exhibited significantly enhanced antibacterial properties against both bacteria and fungi, achieving a pass rating in the challenge test. This example demonstrates that the ether compounds of the present disclosure enhance the effectiveness of soft preservatives, such as phenoxyethanol and benzyl alcohol, advantageously allowing for effective antibacterial activity to be achieved at lower dosage levels of the soft preservatives (e.g., from 0.3% to 0.5% or even 0.4%).

[0150] [Table 8]

[0151] Example 1B Representative serum formulations containing xanthan gum were prepared according to Table 3. As shown in Table 9, when phenoxyethanol (POE), benzyl alcohol, sodium benzoate, or Compound 1 from Table 1 were dispensed alone, none of the serum formulations passed the challenge test. However, when dispensed in combination with phenoxyethanol and Compound 1, benzyl alcohol and Compound 1, and sodium benzoate and Compound 1, each formulation exhibited significantly enhanced antimicrobial properties against both bacteria and fungi. This example demonstrates that the effectiveness of soft preservatives, such as phenoxyethanol, benzyl alcohol, and sodium benzoate, is enhanced when combined with the ether compounds of the present disclosure, advantageously allowing for effective antimicrobial activity to be achieved at lower dosage levels of the soft preservative (e.g., 0.2-0.5%).

[0152] [Table 9]

[0153] Example 1C Representative rinse-off body wash formulations were made according to Table 4. As shown in Table 10, when either phenoxyethanol (POE), benzyl alcohol, or Compound 1 from Table 1 were dispensed alone, none of the body wash formulations passed the challenge test. However, when dispensed in combination with phenoxyethanol and Compound 1 or benzyl alcohol and Compound 1, each body wash formulation exhibited significantly enhanced antimicrobial properties against both bacteria and fungi. This example demonstrates that the effectiveness of soft preservatives, such as phenoxyethanol and benzyl alcohol, is enhanced when combined with the ether compounds of the present disclosure, advantageously allowing for effective antimicrobial activity to be achieved at lower dosage levels of the soft preservative (e.g., 0.3-0.5% or even down to 0.4%).

[0154] [Table 10]

[0155] Example 1D Conventional 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 from Table 1 to enhance the antimicrobial performance of MIT in a typical lotion formulation (Table 2). When used alone at either 5 or 10 ppm, MIT failed to preserve the lotion formulation from bacteria. When MIT was combined with Compound 1, dispensed at a 0.5% level, the preservative performance of MIT was significantly enhanced, and the lotion formulation was successfully preserved from bacteria.

[0156] [Table 11]

[0157] Example 1E Ethyl lauroyl arginate (LAE) is a cationic preservative commonly used in food, home care, and personal care applications. Table 12 shows an example of using compound 1 from Table 1 to enhance the antimicrobial performance of LAE in a nonionic cream formulation (Table 5). When used alone at 1000-4000 ppm, LAE failed to preserve the lotion formulation against bacteria. When LAE at 4000 ppm was combined with compound 1 metered at a 0.5% level, the preservative performance of LAE was significantly enhanced, and the cream formulation was successfully preserved against bacteria.

[0158] [Table 12]

[0159] 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 the use of Compound 1 from Table 1 in a representative lotion formulation (Table 2) to enhance the antimicrobial performance of phenoxyethanol compared to the commercial benchmarks EHG and pentylene glycol. Compound 1 demonstrated superior antimicrobial enhancement of POE compared to either ethylhexylglycerin or pentylene glycol (Table 13).

[0160] [Table 13]

[0161] Example 2 Antioxidant properties For the following experiments, the antioxidant properties were studied using the Activated ABTS Antioxidant Assay Kit (Cat# AOX-14, Instruction Manual ZBM0123.00, April 2021) obtained from Zen-Bio. Trolox, a water-soluble analog of α-tocopherol (a commonly known vitamin E antioxidant), was used as a control. The antioxidant properties were studied both intrinsically and in the hydrogel and micellar water personal care compositions.

[0162] The compositions of the hydrogel and micellar water are shown in Table 14 and Table 15, respectively. The hydrogel compositions were prepared by slowly sprinkling xanthan gum powder into a beaker and mixing constantly. The mixture was then heated to 75-80°C and mixed until no signs of phase separation were observed. The hydrogel was then cooled to room temperature and mixed at high speed to remove air bubbles. The micellar water compositions were prepared by adding all ingredients to a beaker and heating the component mixture to 75-80°C. The final product was cooled to room temperature, and the pH was adjusted to 5-5.5 with citric acid solution. The sample compounds were metered into the compositions at the desired weight percentages using a high-speed mixer.

[0163] [Table 14]

[0164] [Table 15]

[0165] To quantify the antioxidant properties, a series of Trolox concentrations (0, 4.7, 9.4, 18.75, 37.5, 75, 150, and 300 μM) was used as a standard curve. The absorbance of Trolox and the multifunctional additive was measured in triplicate using a BioTek Synergy H1 multimode microplate reader at a wavelength of 405 nm. Table 16 summarizes the intrinsic antioxidant properties of each of Compounds 1–4 based on the Trolox equivalent value determined using the activated ABTS test. As shown in Table 16, based on the determined Trolox equivalent values, the alkenyl (e.g., allyl) ether compounds of the present disclosure exhibit significant antioxidant properties, particularly when at least two of R1, R2, or R3 contain an OH group (i.e., Compounds 1, 3, and 4 in this example). In comparison, pentylene glycol (a preservative or preservative-enhancing agent commonly used in personal care products and cosmetics) and benzyl alcohol (a soft preservative commonly used in personal care products and cosmetics) exhibited minimal antioxidant properties, as indicated by low Trolox equivalent values. Additionally, both the Compound 1 / pentylene glycol blend (50% w / w, "Combo 1" in Table 16) and the Compound 1 / benzyl alcohol blend (50% w / w, "Combo 2" in Table 16) exhibited higher Trolox equivalent values ​​than the individual components. This example demonstrates the antioxidant properties of the ether compounds disclosed by this invention and the additional antioxidant performance benefits of blending such compounds with representative preservatives.

[0166] [Table 16]

[0167] Using a high-speed mixer, Compound 1 was dosed into the hydrogel compositions at different concentrations. All hydrogel compositions were diluted 5-fold with assay buffer to ensure the final solution was completely transparent, and an Activated ABTS Assay (i.e., Cat# AOX-14, Instruction Manual ZBM0123.00, April 2021) was performed to ensure that the composition (e.g., translucency) did not contribute to antioxidant properties. As shown in Table 17, the blank hydrogel composition did not exhibit antioxidant properties after 5-fold dilution. In contrast, the hydrogel composition dosed with Compound 1 exhibited increased Trolox equivalent values ​​after 5-fold dilution. This further demonstrates the antioxidant benefits associated with the ether compounds disclosed herein.

[0168] [Table 17]

[0169] Compound 1 was dosed into the micellar water compositions at different concentrations using a high-speed mixer. All micellar water compositions were clear. As shown in Table 18, blank micellar water exhibited antioxidant properties with a Trolox equivalent value of 72 ± 1 μM (Table 15), due to the antioxidant properties of the ingredients used in the composition (e.g., propylene glycol, disodium EDTA, and panthenol). After Compound 1 was dosed, the micellar water exhibited an increase in Trolox equivalent value as the dose level increased. This further demonstrates the antioxidant benefits associated with the ether compounds disclosed by this invention.

[0170] [Table 18]

[0171] Example 3 Surfactant Properties Using a Wilhelmy plate, the surface tension of the aqueous solution was measured with a Kruss K100 Force Tensiometer equipped with a platinum plate. As shown in Table 19, the addition of Compound 1 in Table 1 reduced the surface tension of the aqueous solution. This demonstrates the surfactant properties associated with the ether compounds disclosed by the present invention. Surfactants are commonly used in personal care products, for example, to stabilize leave-on compositions and create cleansing foams in rinse-off compositions.

[0172] [Table 19]

[0173] The oil-water interfacial tension of the test and control samples was measured using the ring pull-off method with a Kruss K100 Force Tensiometer equipped with a Du Nouy ring (platinum-iridium ring) and built-in software. Maximum force was determined using a modern tensiometer equipped with an electronic force sensor, and the rings were washed and dried before each measurement. All measurements were performed at room temperature. As shown in Table 20, the addition of Compound 1 from Table 1 significantly reduced the interfacial tension at the oil-water interface. When Compound 1 (0.5% by weight) was dispensed together with a representative soft preservative, phenoxyethanol (0.5% by weight, totaling 1% by weight), the interfacial tension was lower than samples dispensed with either 1% by weight of phenoxyethanol or 1% by weight of Compound 1. This demonstrates the synergistic emulsifying properties of the ether compounds disclosed by the present invention when combined with soft preservatives, such as phenoxyethanol.

[0174] [Table 20]

[0175] Example 4 Moisturizing properties Glycerin and 2-ethylhexylglycerin are commonly used moisturizing ingredients in personal care compositions. The water activity of 10% and 20% by weight aqueous multifunctional dispersions was measured in an equilibrium setting using an AwTherm (ROTRONIC). The water activity meter was pre-calibrated with humidity standards, and all measurements were performed at 25°C. The water activity parameter is the equilibrated relative humidity of a given sample divided by 100, resulting in a value ranging from 0 to 1. The parameter is a measure of the unbound water molecules in the system and provides a measure of the system's ability to adsorb water and act as a humectant.

[0176] As shown in Table 21, compounds 1-4 in Table 1 showed comparable reductions in water activity at 10% by weight when compared to the two indices glycerin and 2-ethylhexylglycerin. At 20% by weight, glycerin showed the greatest reduction in water activity as a result of the solubility limits of the other samples. This example demonstrates that the ether compounds of the present disclosure can be used as humectants, especially at dosage levels of 10% or less.

[0177] [Table 21]

[0178] Example 5 Chelating properties Chelating properties were measured using the ZenBio Cupric Ion Chelating (CIC) Assay (Cat# AOX-16, Instruction Manual ZBM0125.00, July 2021). The assay measured the sample's ability to chelate free cupric ions in solution, thereby inhibiting the binding of Cu(II) to pyrocatechol violet (PV) to produce 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 percentage of total PV relative to Cu(II) binding. Ethylenediaminetetraacetic acid (EDTA), a well-known chelating agent, was used as a positive control.

[0179] A series of EDTA with seven different concentrations ranging from 0 to 1000 μM was prepared, and their corresponding absorbances were measured and used as a standard curve (% cupric ion chelation vs. EDTA concentration). The following calculation and Equation 1 were applied to determine the percent cupric ion chelation. The background absorbance value was determined by averaging the absorbance values ​​of three background wells (no CuSO4 or sample). This average background absorbance was then subtracted from all sample absorbance values. The maximum absorbance value (Abs max ) was determined by averaging the absorbance values ​​of triplicate wells containing CuSO4, PV, and assay buffer. Abs in Equation 1 試験 was the absorbance of the test sample. Chelation of cupric ions (%) = 100 × (Abs max -Abs 試験 ) / Abs max (Equation 1)

[0180] After log10 transformation of the concentrations, a polynomial curve was used to fit the standard curve (cupric ion chelation (%) vs. EDTA concentration) (R 2 >0.98).

[0181] The chelating activity of each of Compounds 1-4 in Table 1 is shown in Table 22. Based on the determined EDTA equivalent values, the alkenyl (e.g., allyl) ether compounds of the present disclosure, particularly those in which 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 exhibit chelating properties, resulting in negligible (slightly negative) values ​​for % cupric ion chelation after subtraction of background absorbance (i.e., approximately 0 μM EDTA equivalent).

[0182] [Table 22]

Claims

1. Antimicrobial preservatives and a composition of formula (I) 【Chemistry 1】 [In the formula, R 1 -H, -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH or -R 8 -OR 9 and R 2 -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH, -OR 7 , or -R 8 -OR 9 and R 3 -OH, -R 6 -OH, -OR 7 or -R 8 -OR 9 and R 4 -C 2 ~C 5 is alkenyl, R 5 -H, -C 1 ~C 5 Alkyl or -C 2 ~C 5 alkenyl, and R 1 , R 2 and R 3 Regarding R, independently of each other, 6 Ha-C 1 ~C 6 Alkylene or -C 3 ~C 6 is alkenylene, R 7 Ha-C 1 ~C 6 Alkyl or -C 3 ~C 6 is alkenyl, R 8 Ha-C 1 ~C 5 Alkylene or -C 3 ~C 5 is alkenylene, R 9 Ha-C 1 ~C 5 Alkyl or -C 3 ~C 5 is alkenyl, R 1 , R 2 or R 3 at least one of which contains an -OH group] A personal care, cosmetic or home care product composition comprising an ether compound of formula (I).

2. R 1 , R 2 or R 3 The composition of claim 1, wherein at least one of the groups contains an ether group.

3. R 1 , R 2 , or R 3 3. The composition of claim 1, wherein at least two of the groups contain an -OH group.

4. R 1 , R 2 , and R 3 10. The composition of claim 1, wherein each contains an —OH group.

5. R 2 R 6 -OH and R 3 is -OH or -R 6 2. The composition of claim 1, wherein:

6. R 2 OR 7 or -R 8 -OR 9 and R 3 is -OH or -R 6 2. The composition of claim 1, wherein:

7. R 1 H, -C 1 ~C 6 Alkyl or -R 6 7. The composition of claim 1, wherein the hydroxyl group is —OH.

8. R 4 C 2 ~C 3 alkenyl, preferably C 2 8. The composition of claim 1, wherein the alkyl group is alkenyl.

9. R 5 9. The composition of claim 1, wherein

10. R 6 Ga-C 1 ~C 4 Alkylene or -C 3 ~C 4 is alkenylene, R 7 Ga-C 1 ~C 4 Alkyl or -C 3 ~C 4 is alkenyl, R 8 Ga-C 1 ~C 3 Alkylene or -C 3 is alkenylene, R 9 Ga-C 1 ~C 3 Alkyl or -C 3 is alkenyl, 10. The composition of any one of claims 1 to 9.

11. The ether compound of formula (I) 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 combinations thereof.

12. 12. The composition of any one of claims 1 to 11, wherein the antimicrobial preservative comprises an isothiazolinone, 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, pyrithione, ethyl lauroyl arginate (LAE), or a combination thereof.

13. 13. The composition of any one of claims 1 to 12, wherein the antimicrobial preservative comprises an alkylhydroxamic acid and / or a 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, salts and / or esters of the foregoing acids, zinc pyrithione, sodium pyrithione, or combinations thereof.

14. 14. The composition of any one of claims 1 to 13, 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, esters or salts of said organic acids, or combinations thereof, preferably wherein the antimicrobial preservative comprises phenoxyethanol, benzyl alcohol, benzoic acid, salts of benzoic acid, ethyl lauroyl arginate, CMIT, MIT, BIT, or combinations thereof.

15. 15. The composition according to any one of claims 1 to 14, comprising the ether compound of formula (I) in an amount of from about 0.01% to about 5% by weight, based on the total weight of the composition.

16. 16. The composition according to any one of claims 1 to 15, wherein the ether compound of formula (I) has one or more properties selected from antioxidant properties, surfactant properties, moisturizing properties and chelating properties.

17. 1. 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 antimicrobial agent of formula (I) 【Chemistry 2】 [In the formula, R 1 -H, -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH or -R 8 -OR 9 and R 2 -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH, -OR 7 , or -R 8 -OR 9 and R 3 -OH, -R 6 -OH, -OR 7 or -R 8 -OR 9 and R 4 Ha-C 2 ~C 5 is alkenyl, R 5 -H, -C 1 ~C 5 Alkyl or -C 2 ~C 5 alkenyl, and R 1 , R 2 and R 3 Regarding, independently of each other, R 6 Ha-C 1 ~C 6 Alkylene or -C 3 ~C 6 is alkenylene, R 7 Ha-C 1 ~C 6 Alkyl or -C 3 ~C 6 is alkenyl, R 8 Ha-C 1 ~C 5 Alkylene or -C 3 ~C 5 is alkenylene, R 9 Ha-C 1 ~C 5 Alkyl or -C 3 ~C 5 is alkenyl, R 1 , R 2 or R 3 at least one of which contains an -OH group] adding an ether compound of formula (I) to the reaction mixture;

18. 1. A method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care product, cosmetic or home care product composition, comprising: 【Transformation 3】 [In the formula, R 1 -H, -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH or -R 8 -OR 9 and R 2 -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH, -OR 7 , or -R 8 -OR 9 and R 3 -OH, -R 6 -OH, -OR 7 or -R 8 -OR 9 and R 4 Ha-C 2 ~C 5 is alkenyl, R 5 -H, -C 1 ~C 5 Alkyl or -C 2 ~C 5 alkenyl, and R 1 , R 2 and R 3 Regarding, independently of each other, R 6 Ha-C 1 ~C 6 Alkylene or -C 3 ~C 6 is alkenylene, R 7 Ha-C 1 ~C 6 Alkyl or -C 3 ~C 6 is alkenyl, R 8 Ha-C 1 ~C 5 Alkylene or -C 3 ~C 5 is alkenylene, R 9 Ha-C 1 ~C 5 Alkyl or -C 3 ~C 5 is alkenyl, R 1 , R 2 or R 3 at least one of which contains an -OH group] The method of claim 1, further comprising the step of combining or mixing the compound with an ether compound of formula (I).

19. For enhancing the antimicrobial efficacy of antimicrobial preservatives in personal care, cosmetic or home care product compositions, a compound of formula (I): 【Chemistry 4】 [In the formula, R 1 -H, -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH or -R 8 -OR 9 and R 2 -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH, -OR 7 , or -R 8 -OR 9 and R 3 -OH, -R 6 -OH, -OR 7 or -R 8 -OR 9 and R 4 Ha-C 2 ~C 5 is alkenyl, R 5 -H, -C 1 ~C 5 Alkyl or -C 2 ~C 5 alkenyl, and R 1 , R 2 and R 3 Regarding R, independently of each other, 6 Ha-C 1 ~C 6 Alkylene or -C 3 ~C 6 is alkenylene, R 7 Ha-C 1 ~C 6 Alkyl or -C 3 ~C 6 is alkenyl, R 8 Ha-C 1 ~C 5 Alkylene or -C 3 ~C 5 is alkenylene, R 9 Ha-C 1 ~C 5 Alkyl or -C 3 ~C 5 is alkenyl, R 1 , R 2 or R 3 at least one of which contains an -OH group] Use of ether compounds.

20. Antimicrobial preservatives and a composition of formula (I) 【Transformation 5】 [In the formula, R 1 -H, -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH or -R 8 -OR 9 and R 2 -C 1 ~C 6 Alkyl, -C 2 ~C 6 Alkenyl, -R 6 -OH, -OR 7 , or -R 8 -OR 9 and R 3 -OH, -R 6 -OH, -OR 7 or -R 8 -OR 9 and R 4 Ha-C 2 ~C 5 is alkenyl, R 5 -H, -C 1 ~C 5 Alkyl or -C 2 ~C 5 alkenyl, and R 1 , R 2 and R 3 Regarding R, independently of each other, 6 Ha-C 1 ~C 6 Alkylene or -C 3 ~C 6 is alkenylene, R 7 Ha-C 1 ~C 6 Alkyl or -C 3 ~C 6 is alkenyl, R 8 Ha-C 1 ~C 5 Alkylene or -C 3 ~C 5 is alkenylene, R 9 Ha-C 1 ~C 5 Alkyl or -C 3 ~C 5 is alkenyl, R 1 , R 2 or R 3 at least one of which contains an -OH group] wherein the combined weight of the antimicrobial preservative and the ether compound of formula (I) constitutes at least 75% by weight, preferably at least 90% by weight, based on the total weight of the active ingredients in the antimicrobial composition.

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