Multifunctional enhancer for antimicrobial preservative and application thereof

Abstract

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

Description

Technical Field

[0001] The present invention generally relates to multifunctional enhancers for enhancing the antimicrobial activity of antimicrobial preservatives and their use in personal care products, cosmetics, and household care products, and more particularly, to certain ether compounds as such multifunctional enhancers. Background Art

[0002] Protection against microbial contamination of personal care products, cosmetics, and household care products is very important for these product industries. Traditional preservatives such as isothiazolinones, formaldehyde releasers, parabens (nipagin) and IPBC are under strict scrutiny by regulatory agencies and the Environmental Working Group. In many cases, product formulators are seeking solutions to reduce the dose levels of traditional preservatives without compromising the level of preservation. Many product formulators are also turning to "soft" preservatives such as phenoxyethanol, alcohols, and / or organic acids. Since soft preservatives alone, especially at the required dose levels, generally do not provide a strong broad-spectrum antimicrobial efficacy, formulators may use them in combination with enhancer compounds to provide more effective protection for the product composition.

[0003] In addition, many product compositions include ingredients that are not directly beneficial to the target substrate but are necessary to provide rheological or other chemical and / or mechanical properties to the applied product. Many of these ingredients may cause incidental and undesirable effects, including, for example, an increased tendency to form stickiness or residues and a reduced consumer perception of desirable sensory or manageability attributes. In addition, there is also an increasing demand for product formulations that provide multiple benefits in one product or product application.

[0004] WO 2014 / 191258 A2 relates to antimicrobial compositions containing certain glycerol ethers, and WO 2022 / 128882 A1 relates to the combination of n-heptyl glycerol ether and certain preservative compounds. These references do not disclose the enhancement of antimicrobial preservative activity or the multifunctional properties of the alkenyl ether compounds of formula (I) of the present disclosure (e.g., allyl ether compounds), the compounds of the present invention as described herein.

[0005] There is a need to provide enhancer compounds that increase the antimicrobial efficacy of antimicrobial preservatives in personal care, cosmetic, and household care product compositions, thereby reducing the amount and / or concentration of antimicrobial preservatives required to achieve adequate protection. In addition, there is a need to provide compounds with multifunctional benefits such as antioxidant, surfactant, humectant, and / or chelating properties, enabling formulators to prepare products with reduced numbers and / or amounts of ingredients without compromising (and even potentially enhancing) the benefits of the final product.

[0006] The present application addresses these needs and is based on the unexpected discovery that the ether compounds of formula (I) disclosed herein act as potentiators to enhance the antimicrobial activity of antimicrobial preservatives, thereby allowing for broad-spectrum antimicrobial efficacy to be achieved while reducing the amount and / or concentration of antimicrobial preservatives required to achieve adequate broad-spectrum protection. The present disclosure is also based on the discovered multifunctional nature of the ether compounds of the present disclosure, as it has unexpectedly been found that these compounds exhibit one or more further properties that can be provided in a product formulation, such as one or more of antioxidant, surfactant, humectant, and / or chelating properties. Summary of the Invention

[0007] The present invention provides a personal care, cosmetic, or household care product composition comprising an antimicrobial preservative and an ether compound of formula (I)

[0008]

[0009] wherein R1 is H, -C1-C6 alkyl, -C2-C6 alkenyl, -R6-OH or -R8-O-R9;

[0010] R2 is -C1-C6 alkyl, -C2-C6 alkenyl, -R6-OH, -O-R7 or -R8-O-R9;

[0011] R3 is -OH, -R6-OH, -O-R7 or -R8-O-R9;

[0012] R4 is -C2-C5 alkenyl; and

[0013] R5 is H, -C1-C5 alkyl or -C2-C5 alkenyl; and, relative to R1, R2, and R3 independent of each other, 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.

[0014] In another aspect, a method of providing antimicrobial activity (e.g., controlling or inhibiting the growth of microorganisms in a product composition) to a personal care, cosmetic, or household care product composition is provided, comprising adding an antimicrobial preservative and an ether compound of formula (I) as described herein to the composition.

[0015] In a further aspect, the present disclosure provides the use of an ether compound of formula (I) as described herein for enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic, or household care product composition.

[0016] In another aspect, there is provided a method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or household care product composition, which comprises combining or mixing the antimicrobial preservative with an ether compound of formula (I) as described herein. The antimicrobial effect is enhanced as compared to an equal amount of the antimicrobial preservative without the ether compound.

[0017] In a further aspect, there is provided a method of reducing the minimum amount of an antimicrobial preservative required for preservative activity in a personal care, cosmetic or household care product composition, the method comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) as described herein, wherein after said combining or mixing with the ether compound, the minimum amount of the antimicrobial preservative required for preservative activity in the product composition is less than the minimum amount when the antimicrobial preservative is used alone.

[0018] In another aspect, an antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I) as described herein. Detailed Description

[0019] The ether compounds of the present disclosure are ether compounds of formula (I):

[0020]

[0021] wherein R1 is H, -C1-C6 alkyl, -C2-C6 alkenyl, -R6-OH or -R8-O-R9;

[0022] R2 is -C1-C6 alkyl, -C2-C6 alkenyl, -R6-OH, -O-R7 or -R8-O-R9;

[0023] R3 is -OH, -R6-OH, -O-R7 or -R8-O-R9;

[0024] R4 is -C2-C5 alkenyl (e.g., C2-C3 alkenyl); and

[0025] R5 is H, -C1-C5 alkyl (e.g., C1-C3 alkyl) or -C2-C5 alkenyl (e.g., C2-C3 alkenyl).

[0026] With respect to the oxygen-containing groups of R1, R2, and R3 that are independent of each other, 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).

[0027] 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 of the other of R1, R2, and R3 may contain an ether group. In many preferred embodiments, at least two of R1, R2, or R3 contain an -OH group. In these embodiments, the other of R1, R2, or R3 may or may not contain an -OH group or an ether group. In a further embodiment, each of R1, R2, and R3 contains an -OH group.

[0028] In other embodiments, at least one of R1, R2, or R3 contains an -OH group, and the remaining two each contain an ether group.

[0029] It should be understood that the reference to R1, R2, and / or R3 (where applicable) containing an "-OH group" or an "ether group" refers to the corresponding groups described herein from which R1, R2, and / or R3 are selected and that contain the specified functional group (i.e., containing a hydroxyl or an ether). For example, when R3 is considered to contain an -OH group, this means that R3 is -OH or -R6-OH. As a further example, when R3 is considered to contain an ether group, this means that R3 is -O-R7 or -R8-O-R9. The same principle applies herein to the scope in which R1, R2, and / or R3 are considered to have an oxygen-containing group or a functional group.

[0030] Generally, the total carbon number in R1, R2, and R3 together is usually not more than 12, such as not more than 8 or not more than 6. For example, in many embodiments, the total carbon number in R1, R2, and R3 together is in the range of 1-12, such as 2-12, 3-12, or 4-12, usually 1-8, 2-8, 3-8, 4-8, 1-6, 2-6, or 3-6.

[0031] Generally, the total carbon number in R8 and R9 together is usually not more than 6, or in many embodiments, not more than 4.

[0032] More than one ether compound of formula (I) may be present or used in the compositions and methods of the present disclosure.

[0033] Preferably, R1 in formula (I) is H, -C1-C4 alkyl, -C2-C4 alkenyl, -R6-OH or -R8-O-R9, where R6, R8 and R9 are as described herein. For example, in many embodiments, R1 is H, -C1-C4 alkyl, -C2-C4 alkenyl or -R6-OH, typically H, -R6-OH or -C1-C4 alkyl (e.g., methyl or ethyl). In many further embodiments, R1 is -R6-OH or -R8-O-R9, preferably -R6-OH, where R6, R8 and R9 are as described herein.

[0034] Preferably, R2 in formula (I) is -C1-C4 alkyl, -C2-C4 alkenyl, -R6-OH, -O-R7 or -R8-O-R9, where R6-R9 are as described herein. For example, in many embodiments, R2 is -C1-C4 alkyl (e.g., -C1-C2 alkyl) or C2-C4 alkenyl. In many other embodiments, R2 is R6-OH, -O-R7 or -R8-O-R9, preferably R6-OH, where R6-R9 are as described herein.

[0035] R3 in formula (I) is -OH, -R6-OH, -O-R7 or -R8-O-R9, where R6-R9 are as described herein. Preferably, R2 and R3 are each independently selected to have an oxygen-containing 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-R9 are as described herein. R2 and R3 may but need not be the same.

[0036] Preferably, R2 is -R6-OH and R3 is -OH or -R6-OH.

[0037] In other embodiments, at least one of R2 or R3 contains an -OH group and the other contains an ether group. For example, R2 may be -R6-OH and R3 may be -O-R7 or -R8-O-R9. In other embodiments, R2 and R3 are each independently -O-R7 or -R8-O-R9, preferably where R1 is -R6-OH.

[0038] It should be understood that in embodiments where each of R2 and R3 is -R6-OH, each is -O-R7, or each is -R8-O-R9, the R6-R9 groups may, but need not, be the same in each of R2 and R3 (where appropriate) (and this also applies to the R6, R8, and R9 groups of R1 relative to R2 and R3). For example, in many preferred embodiments, each of R2 and R3 is independently -R6-OH, where the R6 of R2 may be different from or the same as the R6 of R3, such as where the R6 of each is the same or different -C1-C6 alkylene or -C1-C4 alkylene (e.g., selected from methylene and ethylene). In another embodiment, in many embodiments, each of R2 and R3 is independently -R8-O-R9, where the R8 and R9 of R2 may be different from or the same as the R8 and R9 of R3 (e.g., where the R8 of each is the same or different -C1-C5 alkylene or -C1-C3 alkylene (e.g., selected from methylene and ethylene), and the R9 of each is the same or different C3-C5 alkenyl (e.g., -C3 alkenyl)). In a further embodiment, R2 is -O-R7 or -R8-O-R9, preferably -R8-O-R9, and R3 is -OH or -R6-OH, such as where R2 is -R8-O-R9 and R3 is -R6-OH (and, for example, where R6 and R8 are each independently an alkylene as described herein, and R9 is an alkenyl as described herein). In a further embodiment, for example, R2 is an alkyl or alkenyl as described herein, and R3 is -OH, -R6-OH, -O-R7, or -R8-O-R9. As described above, it is preferred that at least one of R1, R2, or R3 contains an -OH group, and thus in embodiments where neither R2 nor R3 contains an -OH group, R1 is preferably -R6-OH.

[0039] It should be understood that the selection of R1 as described herein can be made in combination with any combination of R2 and R3 as described herein, preferably where at least one of R1, R2 or R3 contains an -OH group. This also applies to the selection of R2 relative to R1 and R3 and the selection of R3 relative to R1 and R2, preferably in each case where at least one of R1, R2 or R3 contains an -OH group. For example, in many embodiments, any combination of R2 and R3 is selected, preferably where at least one of R2 or R3 contains an -OH group (e.g., R2 is an alkyl, alkenyl or -R6-OH as described herein, and R3 is -OH or -R6-OH), and R1 is H, -R6-OH, an alkyl or alkenyl as described herein, typically H, R6-OH or a C1-C6 alkyl or a C1-C4 alkyl (e.g., methyl or ethyl). In a further embodiment, any combination of R2 and R3 is selected where R2 and R3 each independently have an oxygen-containing functional group, preferably where at least one (or both) of R2 or R3 contains an -OH group, and R1 is H, -R6-OH, an alkyl or alkenyl as described herein, typically H, -R6-OH or a C1-C6 alkyl or a C1-C4 alkyl (e.g., methyl or ethyl).

[0040] R1, R2 and R3 in formula (I) can each independently be selected to have an oxygen-containing functional group as described herein, preferably where 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-R9 are as described herein, preferably where at least one of R1, R2 or R3 contains an -OH group. For example, R1 and R2 can each independently be -R6-OH, and R3 can be -OH or -R6-OH. As described above, R6 in R1, R2 and R3 can be the same or different, e.g., where R6 is the same or different C1-C6 alkylene or C1-C4 alkylene (e.g., selected from methylene and ethylene).

[0041] R4 in formula (I) contains a non-aromatic carbon-carbon double bond. More specifically, R4 is a C2-C5 alkenyl. Preferably, any combination of R1, R2 and R3 as described herein is selected, and R4 is a C2-C3 alkenyl, preferably a C2 alkenyl.

[0042] R5 in formula (I) is H, -C1-C5 alkyl (e.g., C1-C3 alkyl) or C2-C5 alkenyl (e.g., C2-C3 alkenyl). Preferably, any combination of R1-R4 as described herein is selected, and R5 is H. Specifically, for example, where R4 is C2 alkenyl, this means that R4, R5, and the carbon atoms to which they are respectively attached together form an allyl group. In these preferred embodiments, the ether compound of formula (I) is referred to as an allyl ether compound. In other embodiments, R5 is a short-chain alkyl or alkenyl as described herein.

[0043] Depending on the selected chain length, the "alkyl", "alkylene", "alkenyl", and "alkenylene" used herein can be straight-chain or branched-chain.

[0044] Examples of the ether compound of formula (I) include, but are not limited to, 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).

[0045] The ether compound of formula (I) can be synthesized according to known methods or can be obtained as a commercially available compound.

[0046] In a further aspect of the present disclosure, the ether compounds described herein have one or more properties selected from antioxidants, surfactants, humectants, and chelating as described or verified 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 and chelating properties, or at least antioxidant, chelating, and surfactant properties, or at least antioxidant, chelating, surfactant, and humectant properties. For example, in such an embodiment, R2 can be -R6-OH, R3 can be -OH or -R6-OH, and R1 can be as described herein, preferably where R1 is H, -R6-OH, an alkyl or alkenyl as described herein, typically H, R6-OH, or a C1-C6 alkyl or a C1-C4 alkyl (e.g., methyl or ethyl). Preferably, as the above antioxidant property, the ether compound of formula (I) shows a μM Trolox equivalent (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, specifically at least 100 μM TE, at least 125 μM TE, or at least 150 μM TE, where the TE value is determined according to the analysis test protocol of the Activated ABTS Antioxidant Assay Kit (Cat#AOX-14) (Instruction Manual ZBM0123.00, April 2021). Preferably, as the above chelating property, the ether compound of formula (I) shows a μM EDTA equivalent value (i.e., μmol EDTA / L sample) of at least 50 μM EDTA equivalent, more preferably at least 75 μM EDTA equivalent or at least 100 μM EDTA equivalent, specifically at least 150 μM EDTA equivalent, at least 175 μM EDTA equivalent, or at least 200 μM EDTA equivalent, where the EDTA equivalent value is determined according to the analysis test protocol of the Cupric Ion Chelating Assay Kit (Cat#AOX-16) (Instruction Manual ZBM0125.00, July 2021).

[0047] As antimicrobial preservatives, traditional and / or mild preservatives can be used. The ether compounds of formula (I) can be used to reduce the amount and / or dosage required for such antimicrobial preservatives to achieve the desired preservative activity in personal care products, cosmetics and household care products. Suitable antimicrobial preservatives for personal care products, cosmetics and household care products are known in the art. Examples of such traditional preservatives include isothiazolinones (e.g., 5-chloro-2-methyl-4-isothiazolin-3-one (CMIT), 2-methyl-4-isothiazolin-3-one (MIT) and 1,2-benzisothiazolin-3-one (BIT)), formaldehyde releasers (e.g., bronopol and 1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione) and parabens (e.g., methyl paraben, ethyl paraben, propyl paraben and butyl paraben). The antimicrobial preservative can be a mild preservative.

[0048] Preferably, the antimicrobial preservative comprises isothiazolinones (e.g., CMIT, MIT, BIT, combinations thereof), alkylhydroxamic acids and / or their salts (e.g., hexylhydroxamic acid, octylhydroxamic acid, decylhydroxamic acid, lauroyl hydroxamic acid, salts thereof, combinations thereof, preferably octylhydroxamic acid and / or its salts), aromatic aldehydes (e.g., cinnamaldehyde), alcohols (e.g., aromatic alcohols such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamyl alcohol, phenolic compounds such as hydroxyacetophenone, combinations thereof), diols (e.g., bronopol, diols such as 1,2-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., octylene glycol), combinations thereof), glycerol 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, hex-2,4-dienoic acid, 4-hydroxybenzoic acid, combinations thereof), organic acid salts and / or esters (e.g., esters and / or salts of the above organic acids, such as salts of sodium, potassium, calcium, magnesium or ammonium, including, for example, sodium benzoate, potassium sorbate, etc., and esters of methyl, ethyl, propyl, isopropyl, butyl, isobutyl or phenyl, including butyl benzoate, etc.), ethyl lauroyl arginate (LAE) or any combination of the above.

[0049] For example, the antimicrobial preservative may include alkylhydroxamic acids and / or their salts (preferably, caprohydroxamic acid, caprylohydroxamic acid, capric hydroxamic acid, laurohydroxamic acid and / or their salts or combinations thereof, especially caprylohydroxamic acid and / or its salts), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamaldehyde, cinnamyl alcohol, 1,2 - propanediol, 1,3 - butanediol, 1,2 - pentanediol, 1,2 - hexanediol, 1,2 - heptanediol, 1,2 - octanediol (i.e., octyldiol), bronopol, ethylhexylglycerin, chlorphenesin, CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hex - 2,4 - dienoic acid, 4 - hydroxybenzoic acid, salts and / or esters of the above acids, zinc pyrithione, sodium pyrithione or combinations thereof.

[0050] Preferably, the antimicrobial preservative includes isothiazolinones, aromatic aldehydes, aromatic alcohols, aromatic ethers, organic acids, organic acid salts or esters, pyrithione, ethyl lauroyl arginate (LAE) or combinations thereof.

[0051] Specifically, the antimicrobial preservative may include caprylohydroxamic 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, hex - 2,4 - dienoic acid, 4 - hydroxybenzoic acid, esters or salts of the organic acids (e.g., sodium benzoate, potassium sorbate, etc.) or combinations thereof. For example, the antimicrobial preservative may include phenoxyethanol, benzyl alcohol, benzoic acid, benzoates (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT or combinations thereof.

[0052] More than one antimicrobial preservative may be present or used in the compositions and methods of the present disclosure.

[0053] The optimized amounts of the ether compounds and antimicrobial preservatives of the present application may vary depending on, for example, the specific compounds and preservatives selected, the end - use application, the desired level of preservation, the final properties of the product, etc. Generally, compared to an equal amount of antimicrobial preservative without the ether compound, the ether compound is present in an amount effective to enhance the antimicrobial efficacy of the antimicrobial preservative in the product composition (such as a personal care, cosmetic or household care composition) (e.g., to enhance the desired preservation, antibacterial and / or antifungal effects), for example, to meet or even exceed industry standards for antimicrobial efficacy. In addition, the amount of the ether compound may also be affected by the desired multifunctional benefits such as one or more of the antioxidant, surfactant, humectant and / or chelating properties described herein.

[0054] For example, preferably, in formula (I), at least two of R1, R2 or R3 contain an -OH group (for example, R2 is -R6-OH, R3 is -OH or -R6-OH, and R1 is as described herein, preferably where R1 is H, -R6-OH, an alkyl or alkenyl group as described herein, typically H, R6-OH or a C1-C6 alkyl or C1-C4 alkyl group (for example, methyl or ethyl)), and the amount of the ether compound in the product composition provides at least one chelating property for the product composition. Preferably, at least two of R1, R2 or R3 contain an -OH group (for example, R2 is -R6-OH, R3 is -OH or -R6-OH, and R1 is as described herein, preferably where R1 is H, -R6-OH, an alkyl or alkenyl group as described herein, typically H, R6-OH or a C1-C6 alkyl or C1-C4 alkyl group (for example, methyl or ethyl)), and the amount of the ether compound provides at least antioxidant properties for the product composition. More preferably, at least two of R1, R2 or R3 contain an -OH group (for example, R2 is -R6-OH, R3 is -OH or -R6-OH, and R1 is as described herein, preferably where R1 is H, -R6-OH, an alkyl or alkenyl group as described herein, typically H, R6-OH or a -C1-C6 alkyl or -C1-C4 alkyl group (for example, methyl or ethyl)), and the amount of the ether compound provides at least antioxidant and chelating properties for the product composition, or at least antioxidant, chelating and surfactant properties for the product composition, or at least antioxidant, chelating, surfactant and humectant properties for the product composition. Preferably, when providing the above antioxidant properties to the product composition, an amount of the ether compound of formula (I) as disclosed herein, such as the exemplary amounts disclosed herein (for example, based on the weight of the composition, from about 0.01 wt%, from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 5 wt%, preferably to about 3 wt%, to about 2 wt%, more preferably to about 1.5 wt% or to about 1 wt%), can be used in the product composition, so that the μM Trolox equivalent value of the composition (i.e., μmol Trolox / L sample) is increased by at least 10%, more preferably at least 15%, at least 20% or at least 25%, especially at least 30%, at least 40% or at least 50% compared to the μM Trolox equivalent value of the composition without the ether compound of formula (I), where the μM Trolox equivalent value is determined according to the test protocol of the Activated ABTS Antioxidant Assay Kit (Cat#AOX-14) (Instruction Manual ZBM0123.00, April 2021).Preferably, when providing the above chelating properties to the product composition, a certain amount of the ether compound of formula (I) can be used in the product composition, such as the exemplary amounts disclosed herein (e.g., from about 0.01 wt%, from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt%, or from about 0.5 wt% to about 5 wt%, preferably up to about 3 wt%, up to about 2 wt%, more preferably up to about 1.5 wt% or up to about 1 wt% based on the weight of the composition), so that the μM EDTA equivalent value of the composition (i.e., μmol EDTA / L sample) is increased by at least 10%, more preferably at least 15%, at least 20% or at least 25%, especially at least 30%, at least 40% or at least 50% compared to the μM EDTA equivalent value of the composition without the ether compound of formula (I), wherein the μM EDTA equivalent value is determined according to the analysis test protocol of the copper ion chelation analysis test kit (Cat# AOX-16) (Instruction Manual ZBM0125.00 July 2021).

[0055] Generally, the weight ratio of the ether compound to the antimicrobial preservative can be in the range of about 1:50 - about 50:1, such as about 1:20 - about 20:1, about 1:15 - about 15:1, about 1:10 - about 10:1 or about 1:5 - about 5:1, but other ratios can also be used. This application provides the use of the ether compound and antimicrobial preservative of the present disclosure in product compositions such as personal care products, cosmetics and household care products. Generally, based on the weight of the product composition, the ether compound and the antimicrobial preservative can each be present in an amount ranging from about 0.001 wt%, from about 0.005 wt%, preferably from about 0.01 wt%, from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 5 wt%, preferably up to about 3 wt%, up to about 2 wt%, more preferably up to about 1.5 wt% or up to about 1 wt% according to any combination of the above lower and upper limits and any range therebetween. Depending on the antimicrobial preservative, even lower amounts of the antimicrobial preservative can be used, such as from about 0.0001 wt% or higher, or from about 0.0005 wt% or higher. In some such embodiments, the antimicrobial preservative is isothiazolinone, preferably CMIT, MIT, BIT or a combination thereof. In embodiments where such a small amount of the antimicrobial preservative is used, the weight amount of the ether compound can be substantially proportionally higher than the weight amount of the antimicrobial preservative, such as the ratio of the ether compound to the antimicrobial preservative being as high as 100:1, 500:1, 1000:1, 5000:1 or higher. In some such embodiments, the antimicrobial preservative is isothiazolinone, preferably CMIT, MIT, BIT or a combination thereof.

[0056] Generally, based on the weight of the product composition, for any combination of the above lower and upper limits and any range therebetween, the total amount of the ether compound and the antimicrobial preservative is in the range from about 0.05 wt%, more preferably from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 10 wt%, preferably to about 5 wt%, more preferably to about 3 wt%, to about 2 wt% or to about 1.5 wt% or to about 1 wt%. For example, based on the weight of the product composition, the total amount can be about 0.05 wt% - about 7 wt%, such as about 0.1 wt% - about 5 wt%, about 0.1 wt% - about 4 wt%, about 0.1 wt% - about 3 wt%, or from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 3 wt%, to about 2 wt% or to about 1 wt%.

[0057] Generally, based on the weight of the product composition, the ether compound and the antimicrobial preservative are each present in the product composition in an amount not exceeding about 2 wt%, preferably not exceeding about 1.5 wt% or not exceeding about 1 wt%. Generally, they are each present in an amount less than 1 wt%. Preferably, based on the weight of the product composition, the total amount of the ether compound and the antimicrobial preservative does not exceed about 3 wt% or does not exceed about 2 wt%, such as being in the range from about 1.5 wt% or lower (e.g., from about 0.1 wt% or from about 0.3 wt% - about 1.5 wt%), from about 1.2 wt% or lower (e.g., from about 0.1 wt% or from about 0.3 wt% - about 1.2 wt%) or from about 1 wt% or lower (e.g., from about 0.1 wt% or from about 0.3 wt% - about 1 wt%).

[0058] The ether compound can be combined with the antimicrobial preservative or added to the product composition in any suitable manner. The ether compound can be added to the product composition before, simultaneously with, or after adding the antimicrobial preservative.

[0059] The ether compounds of the present disclosure can be incorporated into any number and variety of different personal care, cosmetic, and household care products, particularly aqueous-based formulations, whether water-soluble or using water as a carrier, including emulsions (whether oil-in-water or water-in-oil). Examples include, but are not limited to, household products and cleaners, fabric detergents, dish detergents, cleaners, soaps, bubble baths, disinfectants, deodorants, hygiene compositions, baby care products, antimicrobial soaps, hand sanitizers, odor removers, antiperspirants, dermatological compositions, skin conditioners, skin moisturizers, anti-wrinkle formulations, sunscreens, tanning lotions, hair care products, shampoos, body washes, conditioners, shaving creams, etc. Personal care products include, for example, products for skin care, hair care, oral care, personal cleansing or hygiene, sun protection, and other applications. Examples of personal care products include shampoos, conditioners, body washes, liquid soaps, skin lotions, and liquids for any personal care wipe applications. Examples of cosmetics include face creams, beauty products, makeup removers, mascaras, and wipes. Examples of household care products include dish soaps, laundry detergents, cleaning wipes, and cleaning formulations.

[0060] Depending on the end-use application, the product composition can contain a variety of different ingredients, i.e., one or more other ingredients suitable for personal care, cosmetic, or household care product compositions. In one embodiment, a personal care composition contains an antimicrobial preservative and an ether compound of formula (I) as described herein, as well as one or more other ingredients suitable for personal care compositions. In another embodiment, a cosmetic composition contains an antimicrobial preservative and an ether compound of formula (I) as described herein, as well as one or more other ingredients suitable for cosmetic compositions. Personal care or cosmetic compositions can be, for example, any formulation for skin care, hair care, makeup, personal cleansing, hygiene, sun protection, and other similar applications. Examples of such products include, but are not limited to, skin darkeners, skin cleansers, night creams, skin creams, shaving creams, skin lotions, beauty products, mascaras, lipsticks, blushes, glosses, eye-liners, makeup removers, sunscreens, lip balms, perfumes, massage oils, shampoos, conditioners, hair styling gels, hair restorers, hair tonics, hair fixatives, hair mousses, bath and shower gels, liquid soaps, moisturizing sprays, bath additives, ophthalmic formulations, foam soaps, and bath liquids, liquids for any personal care wipe applications, etc.

[0061] Depending on the application, the personal care or cosmetic composition can contain a variety of different compatible components, such as any of the following: solvents, surfactants, emulsifiers, rheology modifiers, conditioners, emollients, skin care ingredients, humectants, thickeners, moisturizers, fillers, antioxidants, active ingredients (such as dermatologically active ingredients commonly suitable for topical application), fragrances, etc., and various mixtures thereof.

[0062] As another example, the household care composition contains an antimicrobial preservative and an ether compound of formula (I) as described herein, as well as one or more other ingredients suitable for household care compositions. Examples include dishwashing soaps, laundry detergents, cleaning wipes, cleaning preparations, and other household care applications. Depending on the application, the household care composition can contain, for example, detergents, emulsifiers, surfactants, thickeners, gelling agents, bleaches, optical brighteners, deodorants, enzymes, stabilizers, fragrances, etc., and various mixtures thereof. Examples of the above ingredients and other reagents for personal care, cosmetic, and household care product compositions are known in the art.

[0063] The ether compounds of the present disclosure can be incorporated into various different forms of product compositions, such as, for example, liquids, pastes, serums, hydrogels, creams, lotions, washes, gels, oils, wipes, ointments, semi-solid compositions, and aerosol sprays. For example, they can be used in hair care products, such as shampoos, conditioners, hair dyes, hair tonics, hairgels, hair dressings, hair grooming aids, and other hair care preparations; shaving applications, such as shaving creams, aftershave lotions, and other shaving applications; personal cleansers for the body and hands, such as liquid bath soaps and detergents; perfume preparations, such as perfumes, post-bath sprays, and other similar perfume preparations, skin care products, such as moisturizers, lotions, and creams, and other similar skin care products, beauty products, such as mascaras, base foundations, etc.; makeup remover products, sunscreen products, indoor tanning products, and other similar personal care products; preparations for impregnating wipes for personal cleaning and hygiene, such as, for example, baby wipes, toilet wipes, makeup remover wipes, and exfoliating wipes, etc., or wipe preparations for household care.

[0064] Generally, the product composition has a pH range from about 3.0, from about 4.0, from about 5.0, from about 5.5 or from about 6.0 to about 11, such as about 3.0 - about 10, about 4.0 - about 8.5 or about 5.0 - about 7.5. Unless otherwise indicated, the pH value or range refers to the pH value at room temperature (20 - 25 °C). For example, the selected pH value will vary depending on the specific end - use application. For example, personal care or cosmetic compositions preferably have a pH range from about 3.0 or from about 4.0 to about 8.0, such as from about 4.0 or from about 5.0 to about 7.5 or to about 7.0. Household care compositions preferably have a pH range of about 3.0 to about 11, such as from about 4.0 or from about 5.0 to about 10, or from about 5.0 or from about 6.0 to about 9.0, to about 8.0, to about 7.5 or to about 7.0.

[0065] In another aspect of the present disclosure, a method for providing antimicrobial activity to a personal care, cosmetic or household care product composition is provided, comprising adding an antimicrobial preservative and an ether compound of formula (I) to the composition.

[0066] The present disclosure is not limited to any specific 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 separately to the formulation either simultaneously or in any order.

[0067] In a further aspect, the present disclosure provides the use of the ether compound of formula (I) as described herein for enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or household care product composition.

[0068] In another aspect, a method for enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or household care product composition is provided, comprising combining or mixing the antimicrobial preservative with the ether compound of formula (I) as described herein. The antimicrobial effect is enhanced compared to an equal amount of the antimicrobial preservative without the ether compound.

[0069] In a further aspect, a method for reducing the minimum amount of an antimicrobial preservative required for preservative activity in a personal care, cosmetic or household care product composition is provided, the method comprising combining or mixing the antimicrobial preservative with the ether compound of formula (I) as described herein, wherein after combination or mixing with the ether compound, the minimum amount of the antimicrobial preservative required for preservative activity in the product composition is less than the minimum amount when the antimicrobial preservative is used alone.

[0070] It should be understood that the descriptions herein regarding the ether compounds of formula (I), antimicrobial preservatives, exemplary ratios and dosages, product compositions and ingredients, etc. are also applicable to the methods of the present disclosure.

[0071] According to the present invention, various different microorganisms can be controlled. For example, the combination of an antimicrobial preservative and the ether compound of the present disclosure preferably controls microorganisms such as Gram-positive bacteria, Gram-negative bacteria, and fungi. Non-limiting examples include Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa, Escherichia coli, Enterobacter gergoviae, Klebsiella pneumoniae, Burholderia cepacia, Pseudomonas putida, Candida albicans, Aspergillus brasiliensis, and mixtures thereof. As is known in the art, the antimicrobial effect can be verified by various suitable antimicrobial effect tests. Preferably, when added to a product composition, the antimicrobial preservative and the ether compound of formula (I) provide an antimicrobial effect according to the challenge test protocol in the following examples, achieving a passing growth rating according to the criteria related to Table 7 and the relevant descriptions herein.

[0072] In a further aspect of the present disclosure, the antimicrobial composition comprises an antimicrobial preservative as described herein and an ether compound of formula (I), preferably wherein the antimicrobial preservative and the ether compound of formula (I) together account for 50 wt% - 100 wt% of the active ingredients in the antimicrobial composition, and more preferably wherein the antimicrobial preservative comprises isothiazolinones (e.g., CMIT, MIT, BIT, combinations thereof), alkylhydroxamic acids and / or their salts (e.g., hexahydroxamic acid, octahydroxamic acid, decahydroxamic acid, laurohydroxamic acid, their salts, combinations thereof, preferably octahydroxamic acid and / or its salt), aromatic aldehydes (e.g., cinnamaldehyde), alcohols (e.g., aromatic alcohols such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamyl alcohol, phenolic compounds such as hydroxyacetophenone, and combinations thereof), diols (e.g., bronopol, diols such as 1,2 - propanediol, 1,3 - butanediol, 1,2 - pentanediol, 1,2 - hexanediol, 1,2 - heptanediol, 1,2 - octanediol (i.e., octyl diol), combinations thereof), glycerol ethers (e.g., ethylhexylglycerol, 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, hex - 2,4 - dienoic acid, 4 - hydroxybenzoic acid, combinations thereof), organic acid salts and / or esters (e.g., esters and / or salts of the above - mentioned organic acids, such as sodium, potassium, calcium, magnesium or ammonium salts, including, for example, sodium benzoate, potassium sorbate, etc., and esters of methyl, ethyl, propyl, isopropyl, butyl, isobutyl or phenyl, including butyl benzoate, etc.), ethyl lauroyl arginate (LAE) or combinations thereof.

[0073] For example, the antimicrobial preservative may comprise alkylhydroxamic acids and / or their salts (preferably, hexahydroxamic acid, octahydroxamic acid, decahydroxamic acid, laurohydroxamic acid and / or their salts or combinations thereof, especially octahydroxamic acid and / or its salt), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamaldehyde, cinnamyl alcohol, 1,2 - propanediol, 1,3 - butanediol, 1,2 - pentanediol, 1,2 - hexanediol, 1,2 - heptanediol, 1,2 - octanediol (i.e., octyl diol), bronopol, ethylhexylglycerol, chlorphenesin, CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hex - 2,4 - dienoic acid, 4 - hydroxybenzoic acid, salts and / or esters of the above acids, zinc pyrithione, sodium pyrithione or combinations thereof.

[0074] Preferably, the antimicrobial preservative comprises isothiazolinones, aromatic aldehydes, aromatic alcohols, aromatic ethers, organic acids, organic acid salts or esters, pyrithiones, ethyl lauroyl arginate (LAE) or combinations thereof.

[0075] Specifically, the antimicrobial preservative may include octinoxate, 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, hex-2,4-dienoic acid, 4-hydroxybenzoic acid, esters or salts of the organic acids (e.g., sodium benzoate, potassium sorbate, etc.) or combinations thereof. For example, the antimicrobial preservative may include phenoxyethanol, benzyl alcohol, benzoic acid, benzoates (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT or combinations thereof.

[0076] Generally, the antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I), and based on the total weight of the active ingredients of the antimicrobial composition, their total amount accounts for the majority (>50 wt%) of the active ingredients in the antimicrobial composition, such as at least 60 wt% or at least 70 wt%, preferably at least 80 wt%, more preferably at least 85 wt%, at least 90 wt%, at least 95 wt%, at least 96 wt%, at least 97 wt%, at least 98 wt% or at least 99 wt%. Based on the total weight of the active ingredients in the antimicrobial composition, the antimicrobial composition generally comprises a total amount of about 60 wt% - 100 wt%, preferably about 65 wt% - 100 wt%, about 70 wt% - 100 wt%, about 75 wt% - 100 wt%, about 80 wt% - 100 wt%, about 85 wt% - 100 wt%, about 90 wt% - 100 wt%, or about 95 wt% - 100 wt% or about 97 wt% - 100 wt% of the antimicrobial preservative and the ether compound of formula (I). In many embodiments, the antimicrobial composition comprises active ingredients consisting essentially of an antimicrobial preservative and an ether compound of formula (I), or in further embodiments, comprises active ingredients consisting of an antimicrobial preservative and an ether compound of formula (I).

[0077] Preferably, the antimicrobial composition comprises an antimicrobial preservative and an ether compound of formula (I), the total amount thereof being 50 wt% - 100 wt% of the total weight of the antimicrobial composition, usually accounting for the majority (>50 wt%) of the antimicrobial composition, such as, based on the total weight of the antimicrobial composition, at least 60 wt% or at least 70 wt%, preferably at least 80 wt%, more preferably at least 85 wt%, at least 90 wt%, at least 95 wt%, at least 96 wt%, at least 97 wt%, at least 98 wt% or at least 99 wt%. Based on the total weight of the antimicrobial composition, the antimicrobial composition usually comprises in total about 60 wt% - 100 wt%, preferably about 70 wt% - 100 wt%, about 75 wt% - 100 wt%, about 80 wt% - 100 wt%, about 85 wt% - 100 wt%, about 90 wt% - 100 wt% or about 95 wt% - 100 wt% or about 97 wt% - 100 wt% of the antimicrobial preservative and the ether compound of formula (I). In many embodiments, the antimicrobial composition consists essentially of an antimicrobial preservative and an ether compound of formula (I), or in a further embodiment consists of an antimicrobial preservative and an ether compound of formula (I).

[0078] The antimicrobial composition may, but need not, comprise one or more added solvents or carriers. If present, based on the total weight of the antimicrobial composition, the solvent or carrier usually accounts for from about 10 wt%, from about 20 wt% or from about 30 wt% to about 90 wt%, to about 85 wt%, to about 80 wt%, to about 70 wt%, to about 60 wt% or to about 50 wt%. The solvent or carrier can be selected according to its compatibility or suitability for the desired final application or final product formulation, such as in personal care, cosmetic or household care compositions (e.g., a cosmetically acceptable solvent or carrier). Suitable solvents and carriers include, but are not limited to, water, water-miscible solvents, C1-C4 alcohols, C1-C4 diols (e.g., glycols), glycerol, etc.

[0079] The antimicrobial composition may, but need not, contain one or more excipients in generally small amounts. Similarly, the excipients can be selected based on their compatibility or suitability for the desired end application or final product formulation, such as in personal care, cosmetic or household care compositions (e.g., cosmetically acceptable excipients). Examples of excipients include, but are not limited to, dispersants, solubilizers, buffers and / or stabilizers. Based on the total weight of the antimicrobial composition, the antimicrobial composition can contain, for example, 0 - about 10 wt%, such as from about 0.001 wt%, from about 0.01 wt%, from about 0.05 wt% or from about 0.1 wt% to about 5 wt%, to about 3 wt% or to about 1 wt% of one or more excipients. For example, the amount of the excipient can be in the range of 0 - about 5 wt%, 0 - about 3 wt%, about 0.01 wt% - about 5 wt%, about 0.1 wt% - about 5 wt%, about 0.01 wt% - about 3 wt%, about 0.1 wt% - about 3 wt%, about 0.01 wt% - about 1 wt% or about 0.1 wt% - 1 wt%.

[0080] Generally, the antimicrobial composition can contain in total an amount of about 10 wt% - 100 wt%, such as from about 15 wt% or from about 20 wt%, from about 30 wt%, from about 40 wt%, from about 50 wt% or from about 60 wt% to 100 wt%, to about 99 wt%, to about 97 wt%, to about 95 wt%, to about 90 wt%, to about 80 wt% or to about 70 wt% of an antimicrobial preservative and an ether compound of formula (I) based on the total weight of the antimicrobial composition; optionally, in an amount of 0 - about 90 wt%, such as from about 10 wt%, from about 20 wt% or from about 30 wt% to about 90 wt%, to about 85 wt%, to about 80 wt%, to about 70 wt%, to about 60 wt%, to about 50 wt% or to about 40 wt% of one or more solvents or carriers based on the total weight of the antimicrobial composition; and optionally in an amount of about 0 - about 10 wt%, such as from about 0.001 wt%, from about 0.01 wt%, from about 0.05 wt% or from about 0.1 wt% to about 5 wt%, to about 3 wt% or to about 1 wt% of one or more excipients 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) can be about 10 wt% - about 90 wt%, about 20 wt% - about 80 wt% or about 30 wt% - about 70 wt%, and the amount of the solvent or carrier can be about 10 wt% - about 90 wt%, about 20 wt% - about 80 wt% or about 30 wt% - about 70 wt%, optionally further containing one or more excipients.

[0081] In many embodiments, the antimicrobial composition consists essentially of, or consists of in further embodiments, an antimicrobial preservative, an ether compound of formula (I), optionally one or more solvents or carriers, and optionally one or more excipients.

[0082] The antimicrobial composition can be added to the product composition in an amount effective to achieve the desired level of antimicrobial efficacy or preservation in the product composition. It should be understood that the descriptions herein regarding the ether compound 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 household care product compositions.

[0083] The present disclosure also includes, but is not limited to, the following exemplary embodiments.

[0084] Embodiment 1: An antimicrobial composition comprising an antimicrobial preservative and an ether compound of formula (I)

[0085]

[0086] wherein R1 is H, -C1-C6 alkyl, C2-C6 alkenyl, -R6-OH or -R8-O-R9;

[0087] R2 is -C1-C6 alkyl, -C2-C6 alkenyl, -R6-OH, -O-R7 or -R8-O-R9;

[0088] R3 is -OH, -R6-OH, -O-R7 or -R8-O-R9;

[0089] R4 is -C2-C5 alkenyl; and

[0090] R5 is H, -C1-C5 alkyl or -C2-C5 alkenyl; and, relative to R1, R2 and R3 which are independent of each other, R6 is C1-C6 alkylene or C3-C6 alkenylene,

[0091] R7 is -C1-C6 alkyl or -C3-C6 alkenyl,

[0092] R8 is -C1-C5 alkylene or -C3-C5 alkenylene, and

[0093] R9 is -C1-C5 alkyl or -C3-C5 alkenyl.

[0094] Embodiment 2: A product composition comprising an ether compound of formula (I) and an antimicrobial preservative as described in Embodiment 1, wherein the product composition is selected from personal care products, cosmetics, and household care products.

[0095] Embodiment 3: A method for providing anti-biological activity to a product composition, comprising adding an antimicrobial preservative and an ether compound of formula (I) as described in Embodiment 1 to the product composition, and the product composition is selected from personal care products, cosmetics and household care products.

[0096] Embodiment 4: A method for enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, comprising adding an ether compound of formula (I) as described in Embodiment 1 to the product composition, wherein the product composition is selected from personal care products, cosmetics and household care products.

[0097] Example 5: A method for enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, comprising combining or mixing the antimicrobial preservative with the ether compound described in Embodiment 1, wherein the product composition is selected from personal care products, cosmetics and household care products.

[0098] Example 6: Use of an ether compound of formula (I) as described in Embodiment 1 for enhancing the antimicrobial efficacy of an antimicrobial preservative in a product composition, wherein the product composition is selected from personal care products, cosmetics and household care products.

[0099] Embodiment 7: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-6, wherein at least one of R1, R2 or R3 contains an -OH group.

[0100] Embodiment 8: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-7, wherein at least one of R1, R2 or R3 contains an -OH group, and at least another one of R1, R2 or R3 contains an ether group.

[0101] Embodiment 9: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-8, wherein at least two of R1, R2 or R3 contain an -OH group.

[0102] Embodiment 10: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-7, wherein R1, R2 and R3 each contain an -OH group.

[0103] Embodiment 11: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-10, wherein the total number of carbons in R1, R2 and R3 does not exceed 12, preferably does not exceed 8 or does not exceed 6.

[0104] Embodiment 12: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-11, wherein R1 in formula (I) is H, -R6-OH, -R8-O-R9, -C1-C4 alkyl or -C2-C4 alkenyl; or R1 is H, -R6-OH, -C1-C4 alkyl or -C2-C4 alkenyl; or R1 is H, -R6-OH or -C1-C4 alkyl; or R1 is H, -C1-C4 alkyl or -C2-C4 alkenyl.

[0105] Embodiment 13: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-9, 11 and 12, wherein R2 in formula (I) is -C1-C4 alkyl or -C2-C4 alkenyl.

[0106] Embodiment 14: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-12, wherein R2 in formula (I) is R6-OH, -O-R7 or -R8-O-R9.

[0107] Embodiment 15: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-12 and 14, wherein R2 is R6-OH, and R3 is -OH or -R6-OH.

[0108] Embodiment 16: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-9, 11, 12 and 14, wherein R2 is O-R7 or -R8-O-R9, R3 is -OH or -R6-OH, preferably wherein R2 is -R8-O-R9, and further preferably wherein R1 is H, -R6-OH, -C1-C4 alkyl or -C2-C4 alkenyl, or R1 is H, -R6-OH or -C1-C4 alkyl.

[0109] Embodiment 17: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-16, wherein R4 in formula (I) is C2-C3 alkenyl, preferably C2 alkenyl.

[0110] Embodiment 18: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-17, wherein R5 in formula (I) is H.

[0111] Embodiment 19: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-18, wherein R6 is -C1-C4 alkylene or -C3-C4 alkenylene, R7 is -C1-C4 alkyl or -C3-C3 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.

[0112] Embodiment 20: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-6, wherein the ether compound of formula (I) is selected from

[0113] 2-(allyloxymethyl)-2-ethyl-1,3-propanediol,

[0114] 2,2-bis(allyloxymethyl)-2-ethylpropanediol,

[0115] 3-allyloxy-1,2-propanediol,

[0116] 2,2-bis(hydroxymethyl)-1,3-propanediol allyl ether, and combinations thereof.

[0117] Embodiment 21: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-20, wherein the ratio of the antimicrobial preservative to the ether compound of formula (I) is in the range of about 1:50 - about 50:1, preferably about 1:20 - about 20:1, about 1:15 - about 15:1, about 1:10 - about 10:1, or about 1:5 - about 5:1.

[0118] Embodiment 22: The antimicrobial composition according to any one of Embodiments 1-21, wherein based on the total weight of the active ingredients in the antimicrobial composition, the antimicrobial composition comprises a total of greater than or equal to about 50 wt% of the antimicrobial preservative and the ether compound of formula (I), preferably based on the total weight of the active ingredients in the antimicrobial composition, comprises a total of about 60 wt% - 100 wt%, about 70 wt% - 100 wt%, about 75 wt% - 100 wt%, about 80 wt% - 100 wt%, about 85 wt% - 100 wt%, about 90 wt% - 100 wt%, about 95 wt% - 100 wt%, or about 97 wt% - 100 wt% of the antimicrobial preservative and the ether compound of formula (I).

[0119] Embodiment 23: The antimicrobial composition according to any one of Embodiments 1-22, wherein the antimicrobial composition comprises active ingredients consisting essentially of an antimicrobial preservative and an ether compound of formula (I), or in another embodiment, the antimicrobial composition comprises active ingredients consisting of an antimicrobial preservative and an ether compound of formula (I).

[0120] Embodiment 24: The antimicrobial composition according to any one of Embodiments 1-23, wherein, based on the total weight of the antimicrobial composition, the antimicrobial composition comprises in total greater than or equal to about 50 wt% of an antimicrobial preservative and an ether compound of formula (I), preferably, based on the total weight of the composition, in total about 60 wt%-100 wt%, about 70 wt%-100 wt%, about 75 wt%-100 wt%, about 80 wt%-100 wt%, about 85 wt%-100 wt%, about 90 wt%-100 wt% or about 95 wt%-100 wt% or about 97 wt%-100 wt% of an antimicrobial preservative and an ether compound of formula (I).

[0121] Embodiment 25: The antimicrobial composition according to any one of Embodiments 1-24, wherein the antimicrobial composition consists essentially of an antimicrobial preservative and an ether compound of formula (I), or in a further embodiment, consists of an antimicrobial preservative and an ether compound of formula (I).

[0122] Embodiment 26: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), alkylhydroxamic acid and / or its salts (e.g., hexylhydroxamic acid, octylhydroxamic acid, decylhydroxamic acid, laurohydroxamic acid, salts thereof, combinations thereof, preferably octylhydroxamic acid and / or its salts), aromatic aldehyde (e.g., cinnamaldehyde), alcohol (e.g., aromatic alcohol such as benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamyl alcohol, phenolic compounds such as hydroxyacetophenone, combinations thereof), diol (e.g., bronopol, diols such as 1,2-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., octyldiol), combinations thereof), glycerol ether (e.g., ethylhexylglycerol, chlorphenesin), aromatic ether (e.g., phenoxyethanol), pyrithione (e.g., zinc pyrithione, sodium pyrithione), organic acid (e.g., benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hex-2,4-dienoic acid, 4-hydroxybenzoic acid, combinations thereof), organic acid salts and / or esters (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 of methyl, ethyl, propyl, isopropyl, butyl, isobutyl or phenyl, including butyl benzoate, etc.), ethyl lauroyl arginate (LAE), or combinations thereof.

[0123] Embodiment 27: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises isothiazolinone (e.g., CMIT, MIT, BIT, combinations thereof), aromatic aldehyde (e.g., cinnamaldehyde), aromatic alcohol (e.g., benzyl alcohol, dichlorobenzyl alcohol, phenethyl alcohol, cinnamyl alcohol, phenolic compounds such as hydroxyacetophenone, combinations thereof), aromatic ether (e.g., phenoxyethanol), organic acid (e.g., benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hex-2,4-dienoic acid, 4-hydroxybenzoic acid, combinations thereof), organic acid salts or esters (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 methyl, ethyl, propyl, isopropyl, butyl, isobutyl or phenyl esters, including butyl benzoate, etc.), pyrithione (e.g., zinc pyrithione, sodium pyrithione), ethyl lauroyl arginate (LAE) or combinations thereof.

[0124] Embodiment 28: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises an alkylhydroxamic acid and / or its salt (preferably, caprohydroxamic acid, caprylohydroxamic acid, capric hydroxamic acid, laurohydroxamic acid and / or its salt or a combination thereof, especially caprylohydroxamic acid and / or its salt), phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamaldehyde, cinnamyl alcohol, 1,2-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol (i.e., octyldiol), bronopol, ethylhexylglycerin, chlorphenesin, CMIT, MIT, BIT, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, citric acid, hex-2,4-dienoic acid, 4-hydroxybenzoic acid, salts and / or esters of the above acids, zinc pyrithione, sodium pyrithione or a combination thereof.

[0125] Embodiment 29: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-25, wherein the antimicrobial preservative comprises caprylohydroxamic 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, hex-2,4-dienoic acid, 4-hydroxybenzoic acid, esters or salts of the organic acids (e.g., sodium benzoate, potassium sorbate, etc.) or a combination thereof; or the antimicrobial preservative comprises phenoxyethanol, benzyl alcohol, benzoic acid, benzoates (e.g., sodium benzoate), ethyl lauroyl arginate, CMIT, MIT, BIT or a combination thereof.

[0126] Embodiment 30: The product composition, method or use according to any one of Embodiments 2-21 and 26-29, wherein based on the total weight of the product composition, the ether compound of formula (I) is present in the product composition in a content range from about 0.05 wt%, preferably from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 10 wt%, preferably to about 5 wt%, more preferably to about 3 wt%, to about 2 wt%, especially to about 1.5 wt% or to about 1 wt%.

[0127] Embodiment 31: The product composition, method or use according to any one of Embodiments 2-21 and 26-30, wherein based on the total weight of the product composition, the ether compound of formula (I) and the antimicrobial preservative are each present in the product composition in a content range from about 0.05 wt%, preferably from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 5 wt%, preferably to about 3 wt%, to about 2 wt%, more preferably to about 1.5 wt% or to about 1 wt%.

[0128] Embodiment 32: The product composition, method or use according to any one of Embodiments 2-21 and 26-31, wherein based on the weight of the product composition, the ether compound of formula (I) and the antimicrobial preservative are present in a total amount of from about 0.1 wt%, from about 0.3 wt% or from about 0.5 wt% to about 10 wt%, preferably up to about 5 wt%, more preferably up to about 3 wt%, up to about 2 wt%, up to about 1.5 wt% or up to about 1 wt% in the product composition.

[0129] Embodiment 33: The product composition, method or use according to any one of Embodiments 2-21 and 26-32, wherein based on the weight of the product composition, the ether compound of formula (I) and the antimicrobial preservative are each present in an amount not exceeding 2 wt%, preferably not exceeding 1.5 wt% or not exceeding 1 wt% in the product composition.

[0130] Embodiment 34: The product composition, method or use according to any one of Embodiments 2-21 and 26-33, wherein based on the weight of the product composition, the total amount of the ether compound of formula (I) and the antimicrobial preservative does not exceed 3 wt%, preferably does not exceed 2 wt%, such as from about 1.5 wt% or lower (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.5 wt%), from about 1.2 wt% or lower (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1.2 wt%) or from about 1 wt% or lower (e.g., from about 0.1 wt% or from about 0.3 wt% to about 1 wt%).

[0131] Embodiment 35: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-34, wherein the ether compound of formula (I) has one or more properties selected from the following: antioxidant property, surfactant property, humectant property and chelating property.

[0132] Embodiment 36: The antimicrobial composition, product composition, method or use according to any one of Embodiments 1-12, wherein at least two of R1, R2 or R3 in formula (I) contain an -OH group (for example, wherein R2 is -R6-OH, and R3 is -OH or -R6-OH; preferably wherein R1 is H, -R6-OH, an alkyl or alkenyl group, or is H, -R6-OH or a C1-C6 alkyl group or a C1-C4 alkyl group (such as methyl or ethyl)), and the ether compound of formula (I) has at least antioxidant properties, at least chelating properties, or at least antioxidant and chelating properties, wherein the antioxidant properties have a μM Trolox equivalent (TE) value of at least 25 μM TE, more preferably at least 50 μM TE or at least 75 μM TE, especially at least 100 μM TE, at least 125 μM TE or at least 150 μM TE (i.e., μmol Trolox / L sample), and the chelating properties are a μM EDTA equivalent value of at least 50 μM EDTA equivalent, more preferably at least 75 μM EDTA equivalent or at least 100 μM EDTA equivalent, especially at least 150 μM EDTA equivalent, at least 175 μM EDTA equivalent or at least 200 μM EDTA equivalent (i.e., μmol EDTA / L sample), wherein the Trolox equivalent value is determined according to the analysis test protocol of the activated ABTS antioxidant analysis test kit (Cat#AOX-14) (specification ZBM0123.00, April 2021), and the EDTA equivalent value is determined according to the analysis test protocol of the copper ion chelating analysis test kit (Cat#AOX-16) (specification ZBM0125.00, July 2021), preferably wherein R4 in formula (I) is a C2-C3 alkenyl group (specifically, a C2 alkenyl group), and further preferably wherein R5 in formula (I) is H.

[0133] Embodiment 37: The product composition, method or use according to any one of Embodiments 2-12, wherein at least two of R1, R2 or R3 in formula (I) contain an -OH group (for example, wherein R2 is -R6-OH, and R3 is -OH or -R6-OH, preferably wherein R1 is H, -R6-OH, alkyl or alkenyl, or is H, -R6-OH or -C1-C6 alkyl or -C1-C4 alkyl (for example, methyl or ethyl)), and the amount of the ether compound of formula (I) (for example, according to the amount of any one or combination of Embodiments 30-34) provides at least antioxidant performance, at least chelating performance, or at least antioxidant performance and chelating performance to the product composition, wherein the antioxidant performance provided to the product composition increases by at least 10%, more preferably at least 15%, at least 20% or at least 25%, especially at least 30%, at least 40% or at least 50% in terms of the μM Trolox equivalent value of the composition compared to the μM Trolox equivalent value of the composition in the absence of the ether compound of formula (I), and the chelating performance provided to the product composition increases by at least 10%, more preferably at least 15%, at least 20% or at least 25%, especially at least 30%, at least 40% or at least 50% in terms of the μM EDTA equivalent value of the composition compared to the μM EDTA equivalent value of the composition in the absence of the ether compound of formula (I), wherein the μM Trolox equivalent value of the product composition is determined according to the analysis test protocol of the Activated ABTS Antioxidant Assay Kit (Cat#AOX-14) (Specification ZBM0123.00, April 2021), and the μM EDTA equivalent value of the product composition is determined according to the analysis test protocol of the Copper Ion Chelation Assay Kit (Cat#AOX-16) (Specification ZBM0125.00, July 2021), preferably wherein R4 in formula (I) is C2-C3 alkenyl (specifically, C2 alkenyl), and further preferably wherein R5 in formula (I) is H.

[0134] Embodiment 38: The product composition, method or use according to any one of Embodiments 2-21 and 26-37, wherein the product composition is formulated as a liquid, paste, serum, hydrogel, cream, lotion, emulsion, gel, oil, tissue, ointment, semi-solid composition or aerosol spray.

[0135] Example 39: The product composition, method or use according to any one of Embodiments 2-21 and 26-38, wherein the product composition is a personal care or cosmetic product selected from the following: shampoo, conditioner, shower gel, liquid soap, skin care emulsion, liquid for wet wipes, face cream, hair treatment, beauty makeup and makeup remover.

[0136] Unless otherwise specified, the following terms are defined as follows:

[0137] As used herein, the articles "a", "an" and "the" preceding an element or component of the present invention are intended to be non-limiting with respect to the number of instances (i.e., occurrences) of the element or component. Thus, "a", "an" and "the" should be understood to include one or at least one, and the singular forms of the element or component also include the plural unless the number is clearly singular.

[0138] As used herein, the term "alkyl" refers to a monovalent straight-chain or branched-chain saturated hydrocarbon having a specified number of carbon atoms.

[0139] As used herein, the term "alkylene" refers to a divalent straight-chain or branched-chain saturated hydrocarbon having a specified number of carbon atoms.

[0140] As used herein, the term "alkenyl" refers to a monovalent straight-chain or branched-chain hydrocarbon having at least one carbon-carbon double bond.

[0141] As used herein, the term "alkenylene" refers to a divalent straight-chain or branched-chain hydrocarbon having at least one carbon-carbon double bond.

[0142] As used herein, the term "comprising" means the presence of the recited features, integers, steps or components as in the claims, but does not preclude the presence or addition of one or more other features, integers, steps, components or groups thereof. Unless the context otherwise indicates, the term "comprising" is intended to include the embodiments covered by the terms "consisting essentially of" and "consisting of".

[0143] As used herein, the term "about" modifying the amount of an ingredient or reactant used means, for example, the variation in the numerical amount that may occur by typical measuring and liquid handling procedures used in making concentrates or using solutions in the real world; by inadvertent error in these procedures; by differences in the manufacture, source, or purity of the ingredients used to prepare the composition or carry out the method; and the like.

[0144] If present, all ranges are inclusive and combinable. For example, when referring to a range of "1-5", the recited range should be interpreted to include ranges "1-4", "1-3", "1-2", "1-2 & 4-5", "1-3 & 5", etc.

[0145] When parameters are given as a range, preferred range, or a list of preferred upper and lower values, this should be understood as specifically disclosing all ranges formed by any pair of any upper range or preferred value and any lower range or preferred value, regardless of whether the ranges are disclosed individually. When a numerical range is recited herein, unless otherwise stated, the range is intended to include its endpoints and all integers and fractions within the range. The scope of the present invention is not intended to be limited to the specific values and embodiments recited in the specification.

[0146] Examples

[0147] The following examples demonstrate that when the ether compounds of the present disclosure are incorporated into various product formulations, the preservative effects against a full spectrum of different bacteria and fungi of conventional and mild antimicrobial preservatives (including, but not limited to, phenoxyethanol, sodium benzoate, benzyl alcohol, ethyl lauroyl arginate (LAE), and 2-methyl-4-isothiazolin-3-one (MIT)) are surprisingly improved, thereby enabling a reduction in the levels of conventional or mild preservatives required to protect such products from microbial growth. The ether compounds of the present disclosure also surprisingly (i) exhibit significant antioxidant properties based on the measured Trolox equivalent values and provide antioxidant properties to the product composition; (ii) exhibit humectant properties as evidenced by a reduction in water activity (measured by a Rotronic water activity meter) comparable to known humectant ingredients such as ethylhexylglycerin; (iii) reduce the surface tension after addition to water, confirming surfactant properties; and (iv) exhibit significant chelating properties based on the measured EDTA equivalent values. Table 1 shows the compounds representative of the ether compounds of the present disclosure and used in the following experimental examples.

[0148] Table 1

[0149]

[0150] Example 1. Challenge Test to Verify Enhanced Preservative Action of Conventional and Mild Preservatives

[0151] The preservative activity in representative rinse-off and leave-on product compositions was evaluated using a modified version of the Personal Care Products Council (PCPC) protocol (Machtiger, et al. 2001. Determination of the Efficacy of Preservation of Non-Eye Area Water Miscible Cosmetic and Toiletry Compositions: Collaborative Study. J of AOAC International. 84:1, 101-109).

[0152] This evaluation was conducted using a four-week, two-cycle microbial anti-corrosion efficacy test (challenge test) at 25 °C to determine the anti-corrosion efficacy of each treatment. The ether compounds of the present disclosure were tested alone and in combination with certain antimicrobial preservatives in various product formulations. The compounds were metered in at room temperature and thoroughly mixed into different compositions, including carbomer-containing emulsions (leave-on, Table 2), xanthan gum-containing essence compositions (leave-on, Table 3), body wash formulations (rinse-off, Table 4), and cream formulations (leave-on, Table 5).

[0153] Table 2 shows exemplary compositions of carbomer-based anionic emulsion compositions. Carbomers are commonly used as synthetic rheology modifiers in personal care products. The following compositions were prepared by heating the aqueous phase (A) and the oil phase (B) to 75 - 80 °C separately. Then the oil phase was poured into the aqueous phase and mixed using an overhead mixer and a homogenizer. The oil-in-water emulsion was cooled to room temperature. The pH value was adjusted to 6.0 - 6.5 using triethanolamine.

[0154] Table 2. Representative Emulsion Compositions Containing Carbomer

[0155]

[0156] Table 3 shows an exemplary xanthan gum-based essence. The essence composition was made by adding all the ingredients into a beaker, mixing with an overhead mixer, and heating to 75 - 80 °C. The mixture was homogenized and cooled to room temperature. The pH value was adjusted to pH 5.0 - 5.5 using sodium hydroxide solution.

[0157] Table 3. Representative Essence Compositions Containing Xanthan Gum

[0158]

[0159] Table 4 shows a representative body wash formulation. The composition was made by mixing ACULYN 88 and water in a beaker, and then adding STEOL 230 and AMPHOSOL CA. The solution was mixed using an overhead mixer. The final pH value was adjusted to 6.8 using triethanolamine.

[0160] Table 4. Representative Body Wash Formulations

[0161]

[0162]

[0163] Table 5 shows a representative non-ionic cream formulation. The following composition was prepared by heating the aqueous phase (A) and the oil phase (B) separately to 75 - 80 °C. Then the oil phase was poured into the aqueous phase and mixed by an overhead mixer and a homogenizer. The oil-in-water emulsion was cooled to room temperature. Then SEPIGEL 305 was added to the emulsion. The final pH was adjusted to 5.0 using sodium hydroxide solution.

[0164] Table 5. Representative Non-Ionic Cream Formulations

[0165]

[0166] After metered addition, the sample was divided into two separate aliquots of 5 g each. As described below, one aliquot was inoculated with 50 μL of a dilute bacterial population, and the second aliquot was inoculated with 50 μL of a dilute fungal population. Unpreserved product samples were included in the test as growth controls.

[0167] A mixed bacterial inoculum was prepared using a 24-hour culture of the test bacteria (Table 6) grown in tryptic soy broth (TSB). Equal volumes of the bacterial test strains were combined and diluted 1:10 in phosphate buffer to obtain an inoculum of approximately 5×10 7 -5×10 8 colony-forming units / mL (cfu / mL). The test sample was inoculated with 1% of the mixed bacterial inoculum. A mixed fungal inoculum was prepared using cell suspensions of Candida albicans ATCC#10231 and Aspergillus brasiliensis ATCC#16404 in phosphate buffer. Equal volumes of the fungal test strains were combined and diluted 1:10 in phosphate buffer to obtain an inoculum of approximately 5×10 6 -5×10 7 cfu / mL. The test sample was inoculated with 1% of the mixed fungal inoculum.

[0168] Table 6. Mixed Bacterial Inoculum

[0169] Microorganism ATCC Number Type Burkholderia cepacian 25416 Gram-Negative Non-Fermenter Enterobacter gergoviae 33028 Gram-Negative Fermenter Escherichia coli 8739 Gram-Negative Fermenter Klebsiella pneumoniae 13883 Gram-Negative Fermenter Pseudomonas aeruginosa 9027 Gram-Negative Non-Fermenter Pseudomonas aeruginosa 15442 Gram-Negative Non-Fermenter Pseudomonas putida 49128 Gram-Negative Non-Fermenter Staphylococcus aureus 6538 Gram-Positive Staphylococcus epidermidis 12228 Gram-Positive

[0170] The sample is subjected to a microbial challenge at the zero time point and a second inoculation is carried out after seven days. The number of microorganisms added to each sample is determined by the standard most probable number (MPN) assay in tryptic soy broth (TSB) for bacteria and in potato dextrose broth (PDB) for fungi. The samples are incubated at 25 °C for a four-week test period. The bacterial and fungal contamination of the samples is monitored at 2, 7, 14, 21, and 28 days. The samples challenged with bacteria are streak-plated on tryptic soy agar (TSA) and incubated at 30 °C for 24 hours. The samples challenged with fungi are streak-plated on potato dextrose agar (PDA) and incubated at 25 °C for 7 days. After incubation, the plates are growth-rated to determine the colony-forming units / gram (CFU / g) present in each test sample at the said test time points. Table 7 shows the growth scores. Excellent, good, and passing ratings are all considered to pass the challenge test. As used in various challenge test methods, the passing criteria for bacteria are more stringent than for fungi. For bacteria, a rating of 2, 3, or 4 at 21 days and / or 28 days is considered a failure. For fungi, a rating of 2 at 21 days or 28 days is considered a pass.

[0171] Table 7. Growth Scores for Determining CFU / mL in Test Samples

[0172]

[0173] For the bacterial challenge test, if the composition obtains a growth rating caused by bacteria of 1 or lower at days 21 - 28 of the test period, the composition is rated "pass", and if the composition obtains a growth rating caused by bacteria of 2 or higher at days 21 - 28 of the test period, the composition is rated "fail".

[0174] For the fungal challenge test, if the composition obtains a growth rating caused by fungi of 2 or lower at days 21 - 28 of the test period, the composition is rated "pass", and if the composition obtains a growth rating caused by fungi greater than 2 at days 21 - 28 of the test period, the composition is rated "fail".

[0175] The "pass" rating of the metered-in composition also depends on the unpreserved sample having a "fail" rating.

[0176] Example 1A

[0177] Representative resident emulsion formulations were prepared according to Table 2. As shown in Table 8, when phenoxyethanol (POE), benzyl alcohol (BA), or the compounds in Table 1 were added metered individually, all emulsion formulations failed the challenge test. However, when phenoxyethanol or benzyl alcohol was added metered in combination with the corresponding Compounds 1-4, the emulsion formulations showed significantly enhanced antimicrobial properties against bacteria and fungi, and each formulation received a passing rating in the challenge test. This example shows that the ether compounds of the present disclosure enhance the efficacy of soft preservatives such as phenoxyethanol and benzyl alcohol, and advantageously enable the soft preservatives to obtain effective antimicrobial activity at reduced metered levels (e.g., 0.3%-0.5% or 0.3%-0.4%).

[0178] Table 8. Challenge Test Data - Emulsion Formulations Containing Carbomer

[0179]

[0180]

[0181] Example 1B

[0182] Representative essence 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 in Table 1 were added metered individually, all essence formulations failed the challenge test. However, when the combinations of phenoxyethanol and Compound 1, benzyl alcohol and Compound 1, and sodium benzoate and Compound 1 were added metered respectively, the corresponding formulations showed significantly enhanced antimicrobial properties against bacteria and fungi. This example shows that when combined with the ether compounds of the present disclosure, the efficacy of soft preservatives such as phenoxyethanol, benzyl alcohol, and sodium benzoate is enhanced, and advantageously enables the soft preservatives to obtain effective antimicrobial activity at reduced metered levels (e.g., 0.2%-0.5%).

[0183] Table 9. Challenge Test Data - Essence Compositions Containing Xanthan Gum

[0184]

[0185]

[0186] Example 1C

[0187] Prepare a representative rinse-off body wash formulation according to Table 4. As shown in Table 10, when phenoxyethanol (POE), benzyl alcohol, or Compound 1 in Table 1 was added alone in a measured amount, all body wash formulations failed the challenge test. However, when a combination of phenoxyethanol and Compound 1 or a combination of benzyl alcohol and Compound 1 was added in a measured amount, the corresponding body wash formulations showed significantly enhanced antimicrobial properties against both bacteria and fungi. This example shows that when combined with the ether compounds of the present disclosure, the efficacy of soft preservatives such as phenoxyethanol and benzyl alcohol is enhanced, and advantageously enables the soft preservatives to obtain effective antimicrobial activity at reduced measured levels (e.g., 0.3% - 0.5% or 0.3% - 0.4%).

[0188] Table 10. Challenge test data - Body wash formulations

[0189]

[0190]

[0191] Example 1D

[0192] Traditional isothiazolone preservatives, such as 2-methyl-4-isothiazolin-3-one (i.e., methylisothiazolinone, MIT), are commonly used to protect personal and household care products against bacteria. Table 11 shows an example of enhancing the antimicrobial properties of MIT in a representative emulsion formulation using Compound 1 in Table 1 (Table 2). When used alone at 5 or 10 ppm, MIT failed to protect the emulsion formulation against bacteria. When MIT was combined with Compound 1 added in a measured amount at a level of 0.5%, the preservative properties of MIT were significantly enhanced, and the emulsion formulation successfully resisted bacteria.

[0193] Table 11. Challenge Test Data - Emulsion Formulations Containing Carbomer

[0194]

[0195]

[0196] Example 1E

[0197] Ethyl lauroyl arginate (LAE) is a cationic preservative commonly used in food, household, and personal care applications. Table 12 shows an example of enhancing the antimicrobial properties of LAE in a nonionic cream formulation using Compound 1 in Table 1 (Table 5). When used alone at 1000 - 4000 ppm, LAE did not protect the emulsion formulation against bacteria. When 4000 ppm of LAE was combined with Compound 1 added in a measured amount at a level of 0.5%, the preservative properties of LAE were significantly enhanced, and the cream formulation successfully resisted bacteria.

[0198] Table 12. Challenge Test Data - Non-Ionic Cream Formulations

[0199]

[0200] Example 1F

[0201] Ethylhexylglycerin (EHG) and pentylene glycol (1,2-pentanediol) are commercially available multifunctional ingredients commonly used to enhance the antimicrobial properties of mild preservatives such as phenoxyethanol. Table 13 shows examples of enhancing the antimicrobial properties of phenoxyethanol in a representative emulsion formulation (Table 2) using Compound 1 in Table 1 compared to EHG and pentylene glycol as commercial benchmarks. Compound 1 exhibited excellent antimicrobial enhancement of POE compared to ethylhexylglycerin or pentylene glycol (Table 13).

[0202] Table 13. Challenge Test Data - Emulsion Formulations

[0203]

[0204] Example 2: Antioxidant Performance

[0205] In the following experiment, antioxidant performance was studied using an Activated ABTS Antioxidant Assay Test Kit from Zen-Bio (Cat# AOX-14, Instruction Manual ZBM0123.00, April 2021). Trolox, a water-soluble analog of α-tocopherol (a common vitamin E antioxidant), was used as a reference. Antioxidant performance in hydrogel and micellar water personal care compositions and intrinsically was studied.

[0206] The hydrogel and micellar water compositions are shown in Tables 14 and 15, respectively. The hydrogel composition was prepared by slowly dispersing xanthan gum powder in a beaker with continuous mixing. The mixture was then heated to 75 - 80 °C and mixed until there was no sign of phase separation. The hydrogel was then cooled to room temperature and quickly mixed to remove air bubbles. The micellar water composition was prepared by adding all the ingredients to a beaker and heating the ingredient mixture to 75 - 80 °C. The final product was cooled to room temperature and the pH was adjusted to 5 - 5.5 with a citric acid solution. The sample compound was metered into the composition at the desired wt% using a rapid mixer.

[0207] Table 14. Hydrogel Compositions Containing Xanthan Gum

[0208] Ingredient INCI Name WT% Water Water 99.5 Xanthan Gum Xanthan Gum 0.50

[0209] Table 15. Micellar Water Composition

[0210] Ingredient INCI Name WT% Water Water 92.95 Glycerin Glycerin 1.00 Propylene Glycol Propylene Glycol 0.50 Disodium EDTA Disodium EDTA 0.05 Panthenol Panthenol 1.00 Polyoxyethylene Castor Oil RH PEG-40 Hydrogenated Castor Oil 2.00 EcoSense 3000 Surfactant Decyl Glucoside 1.50 AMISOFT LS-11 Sodium Lauroyl Glutamate 0.50 Pluronic L64 Poloxamer 184 0.50

[0211] A series of Trolox at different concentrations (0, 4.7, 9.4, 18.75, 37.5, 75, 150, and 300 μM) was used as a calibration curve for quantifying antioxidant performance. The absorbance of Trolox and the multifunctional additive was measured in triplicate at a wavelength of 405 nm using a BioTek Synergy H1 multimode microplate reader. Table 16 summarizes the intrinsic antioxidant performance of each of Compounds 1 - 4 based on the Trolox equivalent values determined using the activated ABTS assay. As shown in Table 16, based on the determined Trolox equivalent values, the alkenyl (e.g., allyl) ether compounds of the present disclosure (specifically, where at least two of R1, R2, or R3 contain OH groups) exhibited significant antioxidant performance (i.e., in this example, Compounds 1, 3, and 4). In comparison, pentylene glycol (a preservative or preservative enhancer commonly used in personal care and cosmetics) and benzyl alcohol (a mild preservative commonly used in personal care and cosmetics) showed the lowest antioxidant performance, as indicated by low Trolox equivalent values. Additionally, blends of Compound 1 / pentylene glycol (50% w / w, "Combination 1" in Table 16) and Compound 1 / benzyl alcohol (50% w / w, "Combination 2" in Table 16) both showed higher Trolox equivalent values than the single components. This example verifies the antioxidant performance of the ether compounds of the present disclosure and the further antioxidant performance benefits of blending these compounds with representative preservatives.

[0212] Table 16. Trolox Equivalents (Calculated from Trolox Calibration Curve)

[0213]

[0214] Compound 1 was metered into the above hydrogel compositions at different concentrations using a rapid mixer. The hydrogel compositions were all diluted 5 - fold with analytical test buffer to make the final solution completely transparent, while performing the activated ABTS analytical test (i.e., Cat#AOX - 14, instruction manual ZBM0123.00, April 2021) to ensure that the composition (e.g., translucent) did not contribute to antioxidant performance. As shown in Table 17, the blank hydrogel compositions after 5 - fold dilution did not show antioxidant performance. In contrast, the hydrogel compositions with metered addition of Compound 1 after 5 - fold dilution showed an increase in Trolox equivalent values. This further confirms the antioxidant benefits associated with the ether compounds of the present disclosure.

[0215] Table 17. Trolox Equivalents of Hydrogel (Calculated from Trolox Calibration Curve)

[0216]

[0217] Compound 1 was metered into the above micellar aqueous composition at different concentrations using a rapid mixer. The micellar aqueous compositions were all transparent. As shown in Table 18, due to the antioxidant properties of the ingredients used in the composition such as propylene glycol, disodium EDTA, and panthenol, the blank micellar water showed antioxidant properties with a Trolox equivalent value of 72 ± 1 μM (Table 15). After metering in Compound 1, the Trolox equivalent value of the micellar water increased with the increase in the metering level. This further confirmed the antioxidant benefits associated with the ether compounds of the present disclosure.

[0218] Table 18. Trolox Equivalents of Micellar Water Samples (Calculated from Trolox Calibration Curve)

[0219]

[0220] Example 3: Surfactant Properties

[0221] The surface tension of the aqueous solution was measured using the Wilhelmy plate method on a Krüss K100 force tensiometer equipped with a platinum plate. As shown in Table 19, adding Compound 1 in Table 1 decreased the surface tension of the aqueous solution. This demonstrated the surfactant properties associated with the ether compounds of the present disclosure. Surfactants are commonly used in personal care products, for example, to stabilize leave-on compositions and to generate cleansing foams in rinse-off compositions.

[0222] Table 19. Surface Tension of Water

[0223] Concentration of Compound 1 [mg / L] Surface Tension [mN / m] 0 72.6 20 64.1 200 47.1 500 43.7 800 39.7 1000 37.6 2000 37.3 5000 36.3 7000 35.9 10000 35.6 13000 35.1 15000 35.7 18000 34.9 20000 34.8

[0224] Using the built-in software, the oil-water interfacial tension of the test and control samples was measured by the ring tear method using a Krüss K100 force tensiometer equipped with a Du Noüy ring (platinum-iridium ring). The maximum force was determined using a modern tensiometer with an electronic force sensor, and the ring was cleaned and dried before each measurement. All measurements were carried out at room temperature. As shown in Table 20, adding Compound 1 in Table 1 significantly decreased the interfacial tension between the oil and water. When Compound 1 (0.5 wt%) was metered in together with the representative soft preservative phenoxyethanol (0.5 wt%, a total of 1 wt% in total), the interfacial tension was lower than that of the sample metered with 1 wt% phenoxyethanol or 1 wt% Compound 1, indicating the synergistic emulsifying properties of the ether compounds of the present disclosure when combined with soft preservatives such as phenoxyethanol.

[0225] Table 20. Interfacial Tension between Mineral Oil and Water

[0226] Phase Metered Added Additives and Percentage Levels Interfacial Tension (mN / m) Water (20mL) + Oil (44mL) None 43.6 Water (20mL) + Oil (44mL) 0.5 wt% Phenoxyethanol 25.5 Water (20mL) + Oil (44mL) 1.0 wt% Phenoxyethanol 11.9 Water (20mL) + Oil (44mL) 0.5 wt% Compound 1 19.3 Water (20mL) + Oil (44mL) 1.0 wt% Compound 1 12.8 Water (20mL) + Oil (44mL) 0.5 wt% Phenoxyethanol and 0.5 wt% Compound 1 5.9

[0227] Example 4: Humectant Properties

[0228] Glycerin and 2-ethylhexyl glycerin are commonly used humectants in personal care compositions. The water activity of 10 wt% and 20 wt% aqueous multi-functional dispersions was measured using AwTherm and ROTRONIC water activity in the balance setting. The water activity meter has been pre-calibrated with humidity standards, and all measurements were carried out at 25 °C. The water activity parameter is the equilibrium relative humidity of a given sample divided by 100, and the value ranges from 0 - 1. This parameter is a measure of the amount of unbound water molecules in the system and provides a measure of the ability of the system to adsorb water and act as a humectant.

[0229] As shown in Table 21, compared with the two reference substances glycerin and 2-ethylhexyl glycerin, Compounds 1 - 4 in Table 1 showed a comparable decrease in water activity at 10 wt%. At 20 wt%, due to solubility limitations of other samples, glycerin showed the greatest decrease in water activity. This example shows that the ether compounds of the present disclosure can be used as humectants especially at a dosage addition level of 10% or below 10%.

[0230] Table 21. Water activity measurement

[0231]

[0232] Example 5: Chelating Performance

[0233] The chelating performance was measured using the ZenBio Copper Ion Chelation (CIC) assay method (Cat#AOX - 16, Instruction Manual ZBM0125.00, July 2021). This assay method measures the ability of a sample to chelate free copper ions in solution, thereby inhibiting the binding of Cu(II) to pyrocatecholviolet (PV) to form a highly chromogenic complex. The absorbance of the copper - PV complex was measured at a wavelength of 632 nm. The copper ion chelating activity was determined as the total percentage of PV bound to Cu(II). Ethylenediaminetetraacetic acid (EDTA), a well - known chelating agent, was used as a positive control.

[0234] A series of EDTA with 7 different concentrations (0 - 1000 μM) was prepared, and their corresponding absorbances were measured and used as a calibration curve (copper ion chelation degree (%) vs. EDTA concentration). The following calculations and Equation 1 were applied to determine the percentage of copper ion chelation. The background absorbance value was determined by averaging the absorbance values of the three background wells (without CuSO4 or sample). Then the average background absorbance was subtracted from all sample absorbance values. The maximum absorbance value (Abs 最大 ) was determined by averaging the absorbance values of the three wells containing CuSO4, PV, and assay buffer. Abs 测试 in Equation 1 is the absorbance of the test sample.

[0235] Degree of copper ion chelation (%) = 100 × (Abs 最大 - Abs 测试 ) / Abs 最大 (Equation 1)

[0236] After log10-transforming the concentration (R 2 > 0.98), a calibration curve (degree of copper ion chelation (%) vs. EDTA concentration) is fitted using a polynomial curve.

[0237] The chelating activity of each of Compounds 1 - 4 in Table 1 is shown in Table 22. Based on the measured EDTA equivalent values, the alkenyl (e.g., allyl) ether compounds of the present disclosure, particularly ether compounds in which at least two of R1, R2, or R3 contain OH groups, exhibit significant chelating properties (i.e., in this example, Compounds 1, 3, and 4). In contrast, ethylhexylglycerin (commonly used as part of the preservative system in personal care and cosmetic formulations) and phenoxyethanol (a representative soft preservative commonly used in personal care and cosmetic formulations) do not show chelating properties, and after subtracting the background absorbance (i.e., an EDTA equivalent of approximately 0 μM), the degree of copper ion chelation (%) values are negligible (slightly negative).

[0238] Table 22. EDTA Equivalent (Calculated from the EDTA Calibration Curve)

[0239] Sample Copper ion chelating degree (%) μM EDTA equivalent (μmol EDTA / L sample) Compound 1 in Table 1 53±1 245±4 Compound 2 in Table 1 -7±2 ～0 Compound 3 in Table 1 20±1 170±4 Compound 4 in Table 1 81±2 788±10 Ethylhexylglycerin -1±1 ～0 Phenoxyethanol -6±2 ～0 .

Claims

1. A personal care, cosmetic or household care product composition comprising an antimicrobial preservative and an ether compound of formula (I) 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; and R5 is H, -C1-C5 alkyl or -C2-C5 alkenyl; and, relative to each other independently R1, R2 and R3, R6 is -C1-C6 alkylene or -C3-C6 alkenylene, R7 is -C1-C6 alkyl or -C3-C6 alkenyl, R8 is -C1-C5 alkylene or -C3-C5 alkenylene, and R9 is -C1-C5 alkyl or -C3-C5 alkenyl; and At least one of R1, R2 or R3 contains an -OH group.

2. The composition according to claim 1, wherein at least one of R1, R2 or R3 contains an ether group.

3. The composition according to claim 1 or 2, wherein at least two of R1, R2 or R3 contain an -OH group.

4. The composition according to claim 1, wherein R1, R2 and R3 each contain an -OH group.

5. The composition according to claim 1, wherein R2 is R6-OH, and R3 is -OH or -R6-OH.

6. The composition according to claim 1, wherein R2 is O-R7 or -R8-O-R9, and R3 is -OH or -R6-OH.

7. The composition according to any one of the preceding claims, wherein R1 is H, -C1-C6 alkyl or -R6-OH.

8. The composition according to any one of the preceding claims, wherein R4 is C2-C3 alkenyl, preferably C2 alkenyl.

9. The composition according to any one of the preceding claims, wherein R5 is H.

10. The composition according to any one of the preceding claims, wherein R6 is -C1-C4 alkylene or -C3-C4 alkenylene; R7 is -C1-C4 alkyl or -C3-C4 alkenyl; R8 is -C1-C3 alkylene or -C3 alkenylene; and R9 is -C1-C3 alkyl or -C3 alkenyl.

11. The composition according to claim 1, wherein the ether compound of formula (I) is selected from 2-(allyloxymethyl)-2-ethyl-1,3-propanediol, 2,2-bis(allyloxymethyl)-2-ethylpropanediol, 3-allyloxy-1,2-propanediol, 2,2-bis(hydroxymethyl)-1,3-propanediol allyl ether and combinations thereof.

12. The composition according to any one of the preceding claims, wherein the antimicrobial preservative comprises isothiazolinone, alkylhydroxamic acid and / or its salts, aromatic aldehydes, alcohols, diols, glycerol ethers, aromatic ethers, pyrithione, organic acids, salts and / or esters of organic acids, ethyl lauroyl arginate (LAE) or combinations thereof, preferably wherein the antimicrobial preservative comprises isothiazolinone, aromatic aldehydes, aromatic alcohols, aromatic ethers, organic acids, salts or esters of organic acids, pyrithione, ethyl lauroyl arginate (LAE) or combinations thereof.

13. The composition according to any one of the preceding claims, wherein the antimicrobial preservative comprises alkylhydroxamic acid and / or its salts, phenoxyethanol, benzyl alcohol, hydroxyacetophenone, dichlorobenzyl alcohol, phenethyl alcohol, cinnamaldehyde, cinnamyl 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, hex-2,4-dienoic acid, 4-hydroxybenzoic acid, salts and / or esters of the foregoing acids, zinc pyrithione, sodium pyrithione or combinations thereof.

14. The composition according to any one of the preceding claims, wherein the antimicrobial preservative comprises octylhydroxamic 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, hex-2,4-dienoic acid, 4-hydroxybenzoic acid, esters or salts of these 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. The composition according to any one of the preceding claims, wherein the composition comprises the ether compound of formula (I) in an amount of about 0.01 wt% to about 5 wt% based on the total weight of the composition.

16. The composition according to any one of the preceding claims, wherein the ether compound of formula (I) has one or more properties selected from the group consisting of antioxidant property, surfactant property, humectant property, and chelating property.

17. A method of providing antimicrobial activity to a personal care, cosmetic, or household care product composition, comprising adding an antimicrobial preservative and an ether compound of formula (I) to the composition 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; and R5 is H, -C1-C5 alkyl, or -C2-C5 alkenyl; and, relative to each other independently R1, R2, and R3, R6 is -C1-C6 alkylene or C3-C6 alkenylene; R7 is -C1-C6 alkyl or -C3-C6 alkenyl; R8 is -C1-C5 alkylene or -C3-C5 alkenylene; and R9 is -C1-C5 alkyl or -C3-C5 alkenyl; and at least one of R1, R2, or R3 contains an -OH group.

18. A method of enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic, or household care product composition, comprising combining or mixing the antimicrobial preservative with an ether compound of formula (I) 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; and R5 is H, -C1-C5 alkyl or -C2-C5 alkenyl; and, independently of each other R1, R2 and R3, R6 is -C1-C6 alkylene or -C3-C6 alkenylene, R7 is -C1-C6 alkyl or -C3-C6 alkenyl, R8 is -C1-C5 alkylene or -C3-C5 alkenylene, and R9 is -C1-C5 alkyl or -C3-C5 alkenyl; and at least one of R1, R2 or R3 contains an -OH group.

19. Use of the ether compound of formula (I) for enhancing the antimicrobial efficacy of an antimicrobial preservative in a personal care, cosmetic or household care product composition: 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; and R5 is H, -C1-C5 alkyl or -C2-C5 alkenyl; and, independently of each other R1, R2 and R3, R6 is -C1-C6 alkylene or -C3-C6 alkenylene, R7 is -C1-C6 alkyl or -C3-C6 alkenyl, R8 is -C1-C5 alkylene or -C3-C5 alkenylene, and R9 is -C1-C5 alkyl or -C3-C5 alkenyl; and at least one of R1, R2 or R3 contains an -OH group.

20. An antimicrobial composition comprising an antimicrobial preservative and an ether compound of formula (I): 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; and R5 is H, -C1-C5 alkyl or -C2-C5 alkenyl; and, independently of each other for R1, R2 and R3, R6 is -C1-C6 alkylene or -C3-C6 alkenylene, R7 is -C1-C6 alkyl or -C3-C6 alkenyl, R8 is -C1-C5 alkylene or -C3-C5 alkenylene, and R9 is -C1-C5 alkyl or -C3-C5 alkenyl; and at least one of R1, R2 or R3 contains an -OH group, wherein the total amount of the antimicrobial preservative and the ether compound of formula (I) accounts for at least 75 wt%, preferably at least 90 wt%, based on the total weight of the active ingredients in the antimicrobial composition.

Images