Siloxane derivatives of amino acids having surface-active properties

Abstract

The present disclosure provides siloxane derivatives of amino acids that have surface-active properties. The amino acid can be naturally occurring or synthetic, or they may be obtained via a ring-opening reaction of a lactam, such as caprolactam. The amino acid may be functionalized with a siloxane group to form a compound that is surface-active and has surfactant characteristics. The compounds have low critical micelle concentrations (CMC) as well as the ability to lower the surface tension of a liquid.

Description

PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOSILOXANE DERIVATIVES OF AMINO ACIDS HAVING SURFACE-ACTIVE PROPERTIESCROSS REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit under 35 U.S.C. §119(e) of U.S. Provisional Application Serial No. 63 / 680,060, filed on August 6, 2024, the entire disclosure of which is incorporated by reference herein.FIELD

[0002] The present disclosure pertains to siloxane derivatives of amino acids and methods for their synthesis, wherein the siloxane derivatives have surface-active properties. The present disclosure therefore provides the siloxane derivates of amino acids as surfactants.BACKGROUND

[0003] Surfactants (molecules with surface-active properties) are an important class of molecules with highly sought-after characteristics. Surfactants may be uncharged, zwitterionic, cationic, or anionic. Often, these compounds are amphiphilic molecules with a water-insoluble hydrophobic “tail” group and a water- soluble hydrophilic “head” group. These compounds may adsorb at an interface, such as an interface between two liquids, a liquid and a gas, or a liquid and a solid. In the case of an interface between water and oil, the hydrophilic head group extends into the water, while the hydrophobic tail extends into the oil. When added to water, the hydrophilic head group extends into the water, while the hydrophobic tail extends into the air. The presence of the surfactant disrupts the intermolecular interaction between water molecules, replacing it with weaker interactions between water molecules and the surfactant. This results in lowered surface tension and can also serve to stabilize the interface.

[0004] At sufficiently high concentrations, surfactants may form aggregates to limit the exposure of the hydrophobic tail to the polar solvent. One such aggregate is a micelle, in which the molecules are arranged in a sphere with the hydrophobic tails inside the sphere and the hydrophilic heads on the outside to interact with a polar1DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO solvent. The effect that a given compound has on surface tension and the concentration at which it forms micelles may serve as defining characteristics for a surfactant.

[0005] Surfactants are used in a wide range of commercial applications in formulations ranging from detergents, agricultural products such as herbicidal and other biocidal formulations, surface cleaning agents used in households and industrial and healthcare settings, paints and coating formulations, personal care products ranging from personal hygiene products, to hair care products to cosmetics and the like. In personal care space alone, compounds with surface-active properties are used as soaps, detergents, lubricants, wetting agents, foaming agents, and spreading agents, among others. Surfactants are used in many industrial applications, such as in the micro-electronics / semiconductor chips manufacturing processes, in oil and gas extraction, and in the manufacturing of pharmaceuticals and medicaments, drug delivery vehicles as well as in healthcare facilities such as clinics, physician’s office, and hospitals. Thus, there is an ongoing need to identify new surface-active compounds, synthesize, evaluate and optimize them to make compositions that confer superior surface actions and functionalities in end uses.

[0006] However, solely from its structure, it can be difficult to predict whether a given compound would have surface-active properties or the requisite surface-active properties demanded by the end-use, let alone other important characteristics such as interfacial adsorption dynamics, minimum surface tension achievable, and / or ability to wet hydrophobic and / or oleophobic surfaces, which are also integral to whether the compound would become a useful surfactant. Certain amino acids and their derivatives, for example, are desirable as building blocks for surfactants, but the selection of which amino acids to use is far from intuitive. Likewise, some siloxanes are known to possess surface-active properties, yet predicting, a priori, which siloxane will be effective, in particular end-use applications and conditions and formulations containing other components, is highly challenging if not impossible. Synthesis of such compounds adds another layer of difficulty due to the differences of solubilities attributable to different elements and moieties present in the same2DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WC molecules. There remains a need for high-efficacy surfactants that can be readily synthesized at commercial scale via straightforward routes.SUMMARY

[0007] The present disclosure provides siloxane derivatives of amino acids that can be used as surfactants, as they have surface-active properties. The amino acids may be naturally occurring or synthetic amino acids, or they may be obtained via ring-opening reactions of molecules such as lactams, for example caprolactam. The amino acids may be functionalized with different types of siloxane groups to form compounds with surface-active properties. Characteristically, these compounds may have low critical micelle concentrations (CMC) and / or the ability to reduce the surface tension of a liquid.

[0008] The present disclosure provides a compound of Formula I or a salt thereof, below:Formula I wherein Y is selected from formula (A), (B) or (C)the wave-line denoting the connection to Formula I, whereinR1and R2are linked or otherwise connected together to form a ring that may be substituted or unsubstituted, saturated or unsaturated; optionally the ring may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include3DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO at least one of these atoms at any suitable position on the ring, and the ring may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; wherein the ring formed from R1and R2is optionally linked and / or fused to a further ring;R4and R5may be the same or different from one another, and comprise at least one group selected from the group consisting of Ci-Ce alkyl, optionally the Ci-Ce alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and wherein at least one alkyl chain is substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R3is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, Cs-Cs carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur;R6is optionally present and, if present, is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur; and an optional counterion may be associated with (C) and, if present, the counterion may be selected from the group consisting of chloride, bromide, and iodide; n is an integer from 1 to 12; andX is selected from the group consisting of chloride, bromide, and iodide.

[0009] The compound provided by the present disclosure is a compound of Formula I, wherein in R1and R2form a ring with 4 to 20, for example, with 4 to 15, or with 4 to 10, or with 4 to 8, or with 4 to 6 atoms.

[0010] Y may be selected from piperidine, pyridine, pyrimidine, pyrrole, imidazole, pyrazole, piperazine, or morpholine.

[0011] For example, Y may be selected from4DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0012] Compounds provided by the present disclosure are compounds of Formula I, wherein n is 5. Suitable compounds may be the ones where n is other than 5, however, including those that have n equal to 3, 4, 6, 7, 8, 9, 10, 11 or even 12.

[0013] Compounds provided by the present disclosure include compounds of Formula I, wherein R1and R2form a morpholine structure.

[0014] Compounds provided by the present disclosure include compounds of Formula I, wherein R1and R2form a piperidine structure.

[0015] Compounds provided by the present disclosure include compounds of Formula I, wherein R3is methyl.

[0016] Compounds provided by the present disclosure include compounds of Formula I, wherein Y is (C) and wherein the counterion is present and is selected from the group consisting of chloride, bromide, and iodide.

[0017] Compounds provided by the present disclosure include compounds of Formula I wherein the counterion is chloride.

[0018] Compounds provided by the present disclosure include compounds of Formula I wherein the counterion is iodide.

[0019] Compounds provided by the present disclosure include compounds of Formula I, wherein R3is oxygen.

[0020] Compounds provided by the present disclosure include compounds of Formula I, wherein R3is Ci-Ce alkyl, optionally substituted with hydroxyl.

[0021] One specific compound provided by the present disclosure and referred to herein as Surfactant 1 is5DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO4-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6- oxohexyl)morpholine 4-oxide; having the following formula:Surfactant 1

[0022] A further specific compound provided by the present disclosure and referred to herein as Surfactant 2 is 4-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-4-(3- hydroxypropyl)morpholin-4-ium iodide; having the following formula:Surfactant 2

[0023] A further specific compound provided by the present disclosure and referred to herein as Surfactant 3 is 4-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-4-methylmorpholin-4-ium iodide; having the following formula:Surfactant 3

[0024] A further specific compound provided by the present disclosure and referred to herein as Surfactant 4 is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-6DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO((trimethy Isi ly l)oxy)trisi loxan-3-y l)propy l)am ino)-6-oxohexy l)piperidine 1 -oxide; having the following formula:Surfactant 4

[0025] A further specific compound provided by the present disclosure and referred to herein as Surfactant 5 is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-1-(3- hydroxypropyl)piperidin-1 -ium iodide; having the following formula:Surfactant 5

[0026] A further specific compound provided by the present disclosure and referred to herein as Surfactant 6 is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-1-methylpiperidin-1 -ium iodide; having the following formula:Surfactant 6

[0027] A further specific compound provided by the present disclosure and referred to herein as Surfactant 7 is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy) trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-1 ,4,4- trimethylpiperazine-1 ,4-diium iodide; having the following formula:7DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOSurfactant 7

[0028] A further specific compound provided by the present disclosure and referred to herein as Surfactant 8 is 6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-bis(2-hydroxyethyl)-N-methyl-6- oxohexan-1-aminium iodide; having the following formula:Surfactant 8

[0029] A further specific compound provided by the present disclosure and referred to herein as Surfactant 9 is (2R,3S,4S,5S)-N-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-2,3,4,5,6- pentahydroxy-N-propylhexanamide.Surfactant 9

[0030] The above mentioned and other features of the disclosure, and the manner of attaining them, will become more apparent and will be better understood8DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO by reference to the following description of embodiments taken in conjunction with the accompanying drawings.BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Fig. 1 shows a plot of surface tension versus concentration for Surfactant 1 as described in Example 1 .

[0032] Fig. 2 shows a plot of surface tension versus concentration for Surfactant 2 as described in Example 2.

[0033] Fig. 3 shows a plot of surface tension versus concentration for Surfactant 3 as described in Example 3.

[0034] Fig. 4 shows a plot of surface tension versus concentration for Surfactant 4 as described in Example 4.

[0035] Fig. 5 shows a plot of surface tension versus concentration for Surfactant 5 as described in Example 5.

[0036] Fig. 6 shows a plot of surface tension versus concentration for Surfactant 6 as described in Example 6.

[0037] Fig. 7 shows a plot of surface tension versus concentration for Surfactant 7 as described in Example 7.

[0038] Fig. 8 shows a plot of surface tension versus concentration for Surfactant 8 as described in Example 8.

[0039] Fig. 9 shows a plot of surface tension versus concentration for Surfactant 9 as described in Example 9.

[0040] Fig. 10 shows a plot of surface tension versus concentration for Comparison Surfactant C1 as described in Comparison Example C1.

[0041] Fig. 11 shows a plot of surface tension versus concentration for Comparison Surfactant C2 as described in Comparison Example C2.

[0042] Fig. 12A shows a 3D molecular modeling of a comparison surfactant of Surfactant 6.

[0043] Fig. 12B shows an energy minimized structure of Surfactant 6.

[0044] Fig. 13 is a depiction / cartoon representation of wetting ability and contact angles of several liquid droplets and how the presence or absence of surfactants may affect the shape of the droplets on a hydrophobic surface.9DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WODETAILED DESCRIPTION

[0045] As used herein, the phrase “within any range defined between any two of the foregoing values” means that any range may be selected from any two of the values listed prior to such phrase regardless of whether the values are in the lower part of the listing or in the higher part of the listing. For example, a pair of values may be selected from two lower values, two higher values, or a lower value and a higher value.

[0046] As used herein, the phrase “surface-active” means that the associated compound is able to lower the surface tension of the medium in which it is dissolved, and / or the interfacial tension with other phases, and, accordingly, may be adsorbed at the liquid / vapor and / or other interfaces. For the purposes of this disclosure, the surfactants of the invention are “surface active” compounds.

[0047] With respect terminology of inexactitude, the terms “about” and “approximately” may be used, interchangeably, to refer to a measurement that includes the stated measurement and that also includes any measurements that are reasonably close to the stated measurement. Measurements that are reasonably close to the stated measurement deviate from the stated measurement by a reasonably small amount as understood and readily ascertained by individuals having ordinary skill in the relevant arts. Such deviations may be attributable to measurement error or minor adjustments made to optimize performance, for example. As an illustrative example, for scientific measures involving extensive manual preparations of reagents, when the amounts of such reagents used are small or even minute, and results are sensitive to small changes in terms of the amounts of reagents used, there would likely be a high potential for human errors, or when the instrumentations used are such that small changes in experimental procedures and reagent handling can cause changes in results, especially when the deviations can vary widely and not always reproducible, the term “about” used when reporting such results can be as high as plus or minus 15% of the stated value, for example, plus or minus 15% of the stated value, plus or minus 12% of the stated value, or plus or minus 10% of the stated value, or plus or minus 8% of the stated value, or plus or10DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO minus 6% of the stated value, or plus or minus 4% of the stated value, or even plus or minus 2% of the stated value and the like.

[0048] The present disclosure provides siloxane derivatives of amino acids. The amino acids may be naturally occurring or synthetic, or they may be obtained from ring-opening reactions of lactams, such as caprolactam. The compounds of the present disclosure have been shown to have surface-active properties, and can be used as surfactants including wetting agents, for example.

[0049] The present disclosure provides a compound of Formula I or a salt thereof, below:Formula I wherein Y is selected from formula (A), (B) or (C)the wave-line denoting the connection to Formula I, whereinR1and R2are linked or otherwise connected together to form a ring that may be substituted or unsubstituted, saturated or unsaturated ; optionally the ring may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms at any suitable position on the ring, and the ring may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;11DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO wherein the ring formed from R1and R2is optionally linked and / or fused to a further ring;R4and R5may be the same or different from one another, and comprise at least one group selected from the group consisting of Ci-Ce alkyl, optionally the Ci-Ce alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and wherein at least one alkyl chain is substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R3is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur;R6is optionally present and, if present, is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur; and an optional counterion may be associated with (C) and, if present, the counterion may be selected from the group consisting of chloride, bromide, and iodide; n is an integer from 1 to 12; andX is selected from the group consisting of chloride, bromide, and iodide.

[0050] The compound provided by the present disclosure is a compound of Formula I, wherein in R1and R2form a ring with 4 to 20 atoms, for example, with 4 to 15, or with4 to 10, or with 4 to 8, with 4 to 6 atoms or with 4, 5 or 6 atoms, particularly with 6 atoms.

[0051] For example, Y may be selected from piperidine, pyridine, pyrimidine, pyrrole, imidazole, pyrazole, piperazine, or morpholine.

[0052] Y may be selected from12DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0053] The compound of the present disclosure may be that where n is 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12. In particular, the compound of the present disclosure may be that where n is 5.

[0054] The compound of the present disclosure is a compound of Formula I, wherein R1and R2form a morpholine structure.

[0055] The compound of the present disclosure is a compound of Formula I, wherein R1and R2form a piperidine structure.

[0056] The compound of the present disclosure is a compound of Formula I, wherein R3is methyl.

[0057] The compound of the present disclosure is a compound of Formula I wherein the counterion is chloride.

[0058] The compound of the present disclosure is a compound of Formula I wherein the counterion is iodide.

[0059] The compound of the present disclosure is a compound of Formula I, wherein R3is oxygen.

[0060] The compound of the present disclosure is a compound of Formula I, wherein R3is R1and R2alkyl, optionally substituted with hydroxyl.

[0061] As used herein, the phrase “n may be an integer from 1 to 12” means that n may be equal to 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 , or 12, or within any range including any two of the foregoing as endpoints. In particular, n is from 1 to 8, preferably from 2 to 6, preferably from 3 to 6, more preferably 4 to 6, most preferably 5.

[0062] As used herein, the phrase “Ci-Ce alkyl” means a straight chain or branched alkyl group containing 1 , 2, 3, 4, 5, or 6 carbons or within any range including any two of the foregoing as endpoints.

[0063] As used herein, the phrase “C2-C10 alkenyl” means a straight chain or branched alkenyl group containing 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbons or within any range including any two of the foregoing as endpoints.13DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0064] As used herein, the phrase “C2-C10 alkynyl” means a straight chain or branched alkynyl group containing 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbons or within any range including any two of the foregoing as endpoints.

[0065] As used herein, the phrase “C2-C12 ester” means a straight chain or branched ester group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbons or within any range including any two of the foregoing as endpoints.

[0066] As used herein, the phrase “C2-C12 alkoxy alkyl ether” means a straight chain or branched alkoxy alkyl ether group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbons or within any range including any two of the foregoing as endpoints.

[0067] As used herein, the phrase “C1-C10 hydroxyl” means a hydroxyl attached to a straight chain or branched alkyl group containing 1 , 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbons or within any range including any two of the foregoing as endpoints.

[0068] As used herein, the phrase “C3-C8 carboxylic acid” means a carboxylic acid group attached to a straight chain or branched alkyl group with a containing 3, 4, 5, 6, 7, or 8, carbons or within any range including any two of the foregoing as endpoints.

[0069] As used herein, the phrase “C1-C10 alkyl benzoic acid” means a benzoic acid group attached to a straight chain or branched alkyl group containing 1 , 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbons or within any range including any two of the foregoing as endpoints.

[0070] For the purposes of this disclosure, the compound of Formula (I) or a salt thereof can be:Formula I where Y is14DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOand Z is 0, NR7or CR8and n and R3are defined above; where R7is hydrogen or Ci-Ce alkyl; and R8is hydrogen or Ci-Ce alkyl; preferably, n is 4 to 6, more preferably 5; and / orR3is preferably oxygen, Ci-Ce alkyl or Ci-Ce alkyl substituted with hydroxy; and / or R7is preferably Ci-Ce alkyl, more preferably methyl; and / or R8is preferably hydrogen.

[0071] For the purposes of this disclosure, the compound of Formula (I) or a salt thereof can bethe wave-line denoting the connection to Formula I,R4and R5may be the same or different from one another, and comprise at least one group selected from the group consisting of Ci-Ce alkyl substituted with one or more substituents selected from the group consisting of hydroxyl and carbonyl,R6is selected from the group consisting of Ci-Ce alkyl, preferably methyl, and the counterion is iodide.

[0072] For the purposes of this disclosure, the compound of Formula (I) or a salt thereof can be:15DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOFormula I where n is as defined above, and Y is selected from:preferably where n is from 4 to 6, more preferably 5.

[0073] For the purposes of this disclosure, the compound of Formula (I) or a salt thereof can be:Formula I wherein Y is selected from formula (A), (B) or (C)16DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO the wave-line denoting the connection to Formula I, whereinR1through R6are as defined above, n is 5; andX is selected from the group consisting of chloride, bromide, and iodide.

[0074] One specific compound provided by the present disclosure and referred to herein as Surfactant 1 is4-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6- oxohexyl)morpholine 4-oxide; having the following formula:Surfactant 1

[0075] A further specific compound provided by the present disclosure and referred to herein as Surfactant 2 is 4-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-4-(3- hydroxypropyl)morpholin-4-ium iodide; having the following formula:Surfactant 2

[0076] A further specific compound provided by the present disclosure and referred to herein as Surfactant 3 is 4-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-4-methylmorpholin-4-ium iodide; having the following formula:17DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOSurfactant 3

[0077] A further specific compound provided by the present disclosure and referred to herein as Surfactant 4 is 1 -(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)piperidine 1 -oxide; having the following formula:Surfactant 4

[0078] A further specific compound provided by the present disclosure and referred to herein as Surfactant 5 is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-1-(3- hydroxypropyl)piperidin-1 -ium iodide; having the following formula:Surfactant 5

[0079] A further specific compound provided by the present disclosure and referred to herein as Surfactant 6 is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-1-methylpiperidin-1 -ium iodide; having the following formula:18DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOSurfactant 6

[0080] A further specific compound provided by the present disclosure and referred to herein as Surfactant 7 is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy) trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-1 ,4,4- trimethylpiperazine-1 ,4-diium iodide; having the following formula:Surfactant 7

[0081] A further specific compound provided by the present disclosure and referred to herein as Surfactant 8 is 6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-bis(2-hydroxyethyl)-N-methyl-6- oxohexan-1-aminium iodide; having the following formula:Surfactant 8

[0082] A further specific compound provided by the present disclosure and referred to herein as Surfactant 9 is (2R,3S,4S,5S)-N-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-2,3,4,5,6- pentahydroxy-N-propylhexanamide.19DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOSurfactant 9

[0083] The compounds disclosed herein may be synthesized by various methods. One such method includes reacting an amino siloxane with a ketone to produce a brominated hexanamide intermediate. This intermediate can then undergo nucleophilic substitution to provide the several substituted hexanamides. These substituted hexanamides may then be reacted in a final methylation and epoxidation to yield the quaternary iodide salts, for example.

[0084] Another method to synthesize compounds of the present disclosure may be as follows. This method includes an acylation reaction between an amine and a hexanoyl group, resulting in the formation of a hexanamide. This is followed by a nucleophilic substitution of the bromine using prop-NH2. Lastly, the propylamino hexanamide undergoes nucleophilic followed by ring opening and subsequent attachment of the pyrano-2-one to give the final product.20DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO1.8 g, 93%

[0085] The compounds of the present disclosure are provided for use a surfactants. The present disclosure therefore provides a surfactant of Formula (I) as disclosed above.

[0086] The present disclosure further provides the use of a compound of Formula (I) as disclosed above as a surfactant.

[0087] The compounds of the present disclosure are surfactants and demonstrate surface-active properties. These properties may be measured and described by various methods. One method by which surfactants may be described is by the molecule’s critical micelle concentration (CMC). CMC may be defined as the concentration of a surfactant at which micelles form, and above which all additional surfactant is incorporated into micelles.

[0088] For example, the compounds of formula (I) may have a critical micelle concentration (CMC) from about 0.0010 mmol to about 10.0000 mmol, or from about 0.0500 mmol to about 5.0000 mmol, or from about 0.0500 mmol to about 2.0000 mmol or from about 0.0600 mmol or about 1.3600 mmol, or within any range defined between any two of the foregoing values as endpoints. Critical micelle concentration (CMC) is defined as the surfactant concentration at which micelle formation is first seen in the solution. The surface tension of the solutions at critical micelle concentration (CMC) is defined as yCMC.

[0089] As surfactant concentration increases, surface tension decreases. Once the surface is completely overlaid with surfactant molecules, micelles begin to form. This point represents the CMC, as well as the minimum surface tension.Further addition of surfactant will not further affect the surface tension. CMC may therefore be measured by observing the change in surface tension as a function of21DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO surfactant concentration. One such method for measuring this value is the Wilhemy plate method. A Wilhelmy plate is usually a thin iridium-platinum plate attached to a balance by a wire and placed perpendicularly to the air-liquid interface. The balance is used to measure the force exerted on the plate by wetting. This value is then used to calculate the surface tension (y) according to Equation 1 :Equation 1 : y = F / l cos 0 wherein I is equal to the wetted perimeter (2w + 2d, in which w and d are the plate thickness and width, respectively) and cos 0, the contact angle between the liquid and the plate, is assumed to be 0 in the absence of an extant literature value.

[0090] Another parameter used to assess the performance of surfactants is dynamic surface tension. The dynamic surface tension is the value of the surface tension for a particular surface or interface age. In the case of liquids with added surfactants, this can differ from the equilibrium value. Immediately after a surface is produced, the surface tension is equal to that of the pure liquid. As described above, surfactants reduce surface tension; therefore, the surface tension drops until an equilibrium value is reached. The time required for equilibrium to be reached depends on the diffusion rate and the adsorption rate of the surfactant.

[0091] A plateau value of minimum surface tension that can be reached the compounds of formula (I) may be from about 10.00 mN / m to about 28.00 mN / m, or about 20.00 mN / m to about 25 mN / m, or from about 20.00 mN / m to about 23,00 mN / mm or within any range defined between any two of the foregoing values as endpoints.

[0092] One method by which dynamic surface tension is measured relies upon a bubble pressure tensiometer. This device measures the maximum internal pressure of a gas bubble that is formed in a liquid by means of a capillary. The measured value corresponds to the surface tension at a certain surface age, the time from the start of the bubble formation to the occurrence of the pressure maximum. The dependence of surface tension on surface age can be measured by varying the speed at which bubbles are produced.

[0093] Surface-active compounds may also be assessed by their wetting ability on solid substrates as measured by the contact angle. When a liquid droplet22DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO comes in contact with a solid surface in a third medium, such as air, a three-phase line forms among the liquid, the gas and the solid. The angle between the surface tension unit vector, acting at the three-phase line and tangent at the liquid droplet, and the surface is described as the contact angle. The contact angle (also known as wetting angle) is a measure of the wettability of a solid by a liquid. In the case of complete wetting, the liquid is completely spread over the solid and the contact angle is 0°. Wetting properties are typically measured for a given compound at the concentration of 1-1 Ox CMC; however, it is not a property that is concentrationdependent. Therefore, measurements of wetting properties can be measured at concentrations that are higher or lower.

[0094] In one method, an optical contact angle goniometer may be used to measure the contact angle. This device uses a digital camera and software to extract the contact angle by analyzing the contour shape of a sessile droplet of liquid on a surface.

[0095] The identity surface-active compounds of the instant disclosure may be analyzed and confirmed using nuclear magnetic resonance (NMR) spectroscopy, performed on a Broker 500 MHz spectrometer. The critical micelle concentration (CMC) may be determined by the Wilhelmy plate method at 23° C with a tensiometer (DCAT 11 , DataPhysics Instruments GmbH) equipped with a Pt-lr plate. Dynamic surface tension may be determined with a bubble pressure tensiometer (Kruss BP100, Kruss GmbH), at 23° C. Contact angle may be determined with the optical contact angle goniometer (OCA 15 Pro, DataPhysics GmbH) equipped with a digital camera. The pH was determined using a standard laboratory pH meter.

[0096] The synthesized molecules may further characterized for their thermodynamic behavior at the phase interface, for example using pre-factors determined from Gibbs Thermodynamics equations (shown here) measuring the thermodynamics of the adsorption of a surfactant molecule at a 2-phase interface, typically an air and liquid interface.where R is the gas constant, T is the temperature, C the concentration in the bulk phase.23DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0097] As a general matter, ionic surfactants would necessarily incur the presence of a cation and an ion as they disassociate at the interface, whereas a nonionic surfactant would have just the molecule itself as it dissociates. Pre-factors are used to refer to the surface excess concentration of a substance as it thermodynamically disassociates at a 2-phase interface. Accordingly, an ionic surfactant has a pre-factor (or prefactor) of two (2), which accounts for the two species being cation and the anion as the ionic solution disassociates in water, whereas a nonionic surfactant has a prefactor of one (1).

[0098] Potential applications for the surface-active compounds of the present disclosure include formulations for use as shampoos, hair conditioners, detergents, spot-free rinsing solutions, floor and carpet cleaners, cleaning agents for graffiti removal, wetting agents for crop protection, adjuvants for crop protection, and wetting agents for aerosol spray coatings.

[0099] It will be understood by one skilled in the art that small differences between compounds may lead to substantially different surfactant properties, such that different compounds may be used with different substrates, in different applications. It will be further understood by one skilled in the art that surfactant properties may not be predictable on the basis of chemical structure, as further demonstrated below. For example,

[0100] The following non-limiting embodiments are provided to demonstrate the different properties of the different surfactants. In Table 1 below, short names for the surfactants are correlated with their corresponding chemical structures.TABLE 124DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO25DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0101] These compounds may be effective as surfactants, useful for wetting or foaming agents, dispersants, emulsifiers, and detergents, among other applications.

[0102] The amount of the compounds disclosed herein used in a formulation may be as low as about 0.001 wt.%, about 0.05 wt.%, about 0.1 wt.%, about 0.5 wt.%, about 1 wt.%, about 2 wt.%, or about 5 wt.%, or as high as about 8 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, or about 25 wt.%, or within any range defined between any two of the foregoing values.EXAMPLES

[0103] The identity of each synthesized compound was analyzed and confirmed using nuclear magnetic resonance (NMR) spectroscopy, performed on a26DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOBruker 500 MHz spectrometer. The critical micelle concentration (CMC) was determined by the Wilhelmy plate method at 23° C with a tensiometer (DCAT 11 , DataPhysics Instruments GmbH) equipped with a Pt-lr plate. Dynamic surface tension was determined with a bubble pressure tensiometer (Kruss BP100, Kruss GmbH), at 23° C. Contact angle was determined with the optical contact angle goniometer (OCA 15 Pro, DataPhysics GmbH) equipped with a digital camera. The pH was determined using a standard laboratory pH meter.

[0104] The synthesized molecules were further characterized for their thermodynamic behavior at the phase interface, for example using pre-factors determined from Gibbs Thermodynamics equations (shown here) measuring the thermodynamics of the adsorption of a surfactant molecule at a 2-phase interface, typically an air and liquid interface.where R is the gas constant, T is the temperature, C the concentration in the bulk phase.

[0105] As a general matter, ionic surfactants would necessarily incur the presence of a cation and an ion as they disassociate at the interface, whereas a nonionic surfactant would have just the molecule itself as it dissociates. Pre-factors are used to refer to the surface excess concentration of a substance as it thermodynamically disassociates at a 2-phase interface. Accordingly, an ionic surfactant has a pre-factor (or prefactor) of two (2), which accounts for the two species being cation and the anion as the ionic solution disassociates in water, whereas a nonionic surfactant has a prefactor of one (1).Example 1a: Synthesis of Surfactant 127DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WC

[0106] Synthesis procedure: K2CO3 (2 equiv.,) followed by morpholine (1 equiv) were added to 1 ,5g of starting material of bromo compound (1 equiv.,) in 50 mL of ACN at room temperature and then heated at 70°C for 14h. The reaction mixture was then filtered, the filtrate was diluted with DCM and washed with water. The organic layer concentrated, and crude compound used for next step without any further purification. 1 ,1g of colorless liquid obtained (giving a yield of about 72%).

[0107] NaH2CO3 (2 equiv.,) and mCPBA (1 .2 equiv) was added to 1 g of starting material of morpholine TSS substrate (1 equiv.,) in 30 mL of DCM at 0°C and then left at room temperature for 3h. After completion, the reaction mixture was filtered, and the filtrate was concentrated. The crude compound was then washed with hexanes, then the resulting compound was left to dry under for high vacuum. Eight hundred and fifty (850) mg of yellow sticky liquid was obtained (giving a yield of about 85%).Example 1 b: Determination of physical properties of Surfactant 1

[0108] The critical micelle concentration (CMC) for Surfactant 1 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 0.0107 mM (0.0056 mg / mL) at pH 4. The plateau value of minimum surface tension that can be reached by this surfactant was about 21.28 mN / m, indicating that the surfactant has outstanding interfacial activity. These results were plotted as surface tension versus concentration in Fig. 1 . The molecular parameters of surfactant 1 are summarized below:28DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOExample 2: Synthesis of Surfactant 2

[0109] Iodo propanol (1 .2 equiv) was added to the morpholine TSS substrate described in Example 1 , 1 g of starting material of morpholine TSS substrate (1 equiv.,) in 30 mL of DMF at room temperature and then heated at about 70°C for 14h. The reaction mixture was concentrated, and crude compound was washed with hexanes, and then the resulting compound was dried under high vacuum. Six hundred and fifty (650) mg of white solid was obtained (giving a yield of about 48.5 %).Example 2a: Determination of physical properties of Surfactant 2

[0110] The critical micelle concentration (CMC) for Surfactant 2 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 1.2197 mM (0.8818 mg / mL) at pH 4. The plateau value of the minimum surface tension that can be reached by this surfactant was about 21.12 mN / m, indicating that the surfactant has outstanding interfacial activity. These29DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO results are plotted as surface tension versus concentration in Fig. 2. The molecular parameters of surfactant 2 are summarized below:Example 3: Synthesis of Surfactant 3

[0111] Na2COs (1 equiv.,) followed by lodomethane (1.2 equiv) were added to the morpholine TSS substrate described in Example 1 , (1 equiv.,) in 30 mL of ACN at room temperature and then heated at 40°C for 14h. The reaction mixture was then filtered, the filtrate was concentrated, and the crude compound was washed with hexanes, then the resulting compound dried under high vacuum. Four Hundred (400) mg of white solid was obtained (giving a yield of about 64%).Example 3a: Determination of physical properties of Surfactant 3

[0112] The critical micelle concentration (CMC) for Surfactant 3 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 0.5774 mM (0.3827 mg / mL) at pH 8. The plateau value of minimum surface tension that can be reached by this surfactant was about 20.47 mN / m, indicating that the surfactant has outstanding interfacial activity. These results30DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO are plotted as surface tension versus concentration in Fig. 3. The molecular parameters of surfactant 3 are summarized below:Example 4: Synthesis of Surfactant 4

[0113] Synthesis procedure: K2CO3 (2 equiv.,) followed by N-Methyl piperazine (1 equiv) were added to 1 g of starting material of bromo compound (1 equiv.,) in 50 mL of ACN at room temperature and then heated to 70°C for 14h. The reaction mixture was the filtered, and the filtrate was diluted with DCM and washed with water. The organic layer concentrated, and crude compound used for next step without any further purification. Nine hundred and eighty (980) mg of colorless liquid was obtained (giving a yield of about 98%)31DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WC

[0114] NaH2CO3 (2 equiv.,) followed by mCPBA (1.2 equiv) were added to 1 g of starting material of piperidine TSS substrate (1 equiv.,) in 30 mL of DCM at 0°C and then the mixture was left at room temperature for 3h. Thereafter, the reaction mixture was filtered, the filtrate was concentrated, and the crude compound was washed with hexanes. The resulting compound was left to dry under high vacuum dry. Six hundred (600) mg of yellow liquid was obtained (giving a yield of about 60%).Example 4a: Determination of physical properties of Surfactant 4

[0115] The critical micelle concentration (CMC) for Surfactant 4 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 0.1022 mM (0.0563 mg / mL) at about pH 4. The plateau value of minimum surface tension that can be reached by this surfactant was about 22.23 mN / m, indicating that the surfactant has outstanding interfacial activity. These results are plotted as surface tension versus concentration in Fig. 4. The molecular parameters of surfactant 4 are summarized below:Example 5: Synthesis of Surfactant 532DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WC

[0116] Starting with the piperidine TSS substrate described in Example 4, (1 equiv.,) in 30 mL of DMF Iodo propanol (1.2 equiv) was added, initially at room temperature and then heated at 70°C for 14h. After completion, the reaction mixture was concentrated, and crude compound was washed with hexanes. The compound was then left to dry under high vacuum. Six hundred and twenty (620) mg of white solid was obtained (giving a yield of about 51 %).Example 5a: Determination of physical properties of Surfactant 5

[0117] The critical micelle concentration (CMC) for Surfactant 5 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 0.0677 mM (0.0488 mg / mL) at about pH 5. The plateau value of minimum surface tension that can be reached by this surfactant was about 20.96 mN / m, indicating that the surfactant has outstanding interfacial activity. These results are plotted as surface tension versus concentration in Fig. 5. The molecular parameters of surfactant 5 are summarized below:Example 6: Synthesis of Surfactant 633DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WC

[0118] Na2COs (1 equiv.,) and lodomethane (1.2 equiv) were added to the piperidine TSS substrate described in Example 4, (1 equiv.,) in 30 mL of ACN at room temperature, which mixture was then subject to heating at 40°C for 14h. The reaction mixture was then filtered, the filtrate was concentrated, and the crude compound was then washed with hexanes, and then the compound was left to dry under high vacuum. Four hundred twenty (420) mg of yellow solid was obtained (giving a yield of about 84%).Example 6a: Determination of physical properties of Surfactant 6

[0119] The critical micelle concentration (CMC) for Surfactant 6 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 0.7382 mM (0.4998 mg / mL) at about pH 7. The plateau value of minimum surface tension that can be reached by this surfactant was about 20.37 mN / m, indicating that the surfactant has outstanding interfacial activity. These results are plotted as surface tension versus concentration in Fig. 6. The molecular parameters of surfactant 6 are summarized below:Example 7: Synthesis of Surfactant 734DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0120] Synthesis procedure: K2CO3 (2 equiv.,) followed by N-Methyl piperazine (1 equiv) was added to 1 g of starting material of bromo compound (1 equiv.,) in 50 mL of ACN room temperature. Then the reaction mixture was heated at 70°C for 14h. Thereafter, the reaction mixture was filtered, the filtrate was diluted with DCM, and the filtrate was then washed with water. The organic layer concentrated, and crude compound was used for next step without any further purification. Nine hundred fifty (950) mg of colorless liquid was obtained (giving a yield of about 95%).

[0121] Next, Na2COs (1 equiv.,) followed by lodomethane (2.2 equiv) was added to 500 mg of starting material of piperizine TSS substrate (1 equiv.,) in 30 mL of ACN, at room temperature and then heated at 40°C for 14h. The reaction mixture was then filtered, the filtrate was concentrated, and the crude compound was washed with hexanes. The compound was left to dry under high vacuum. Four hundred and fifty (450) mg of white solid was obtained (giving a yield of about 60%).Example 7a: Determination of physical properties of Surfactant 7

[0122] The critical micelle concentration (CMC) for Surfactant 7 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 0.0571 mM (0.0467 mg / mL) at about pH 6. The plateau value of minimum surface tension that can be reached by this surfactant was about 20.48 mN / m, indicating that the surfactant has outstanding interfacial activity. These results are plotted as surface tension versus concentration in Fig. 7. The molecular parameters of surfactant 7 are summarized below:35DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOExample 8: Synthesis of Surfactant 8

[0123] Synthesis procedure: K2CO3 (2 equiv.,) followed by Diethanolamine (1 equiv) were added to 1 g of starting material of bromo compound (1 equiv.,) in 50 mL of can at room temperature but then heated at 70°C for 14h. The reaction mixture was the filtered, the filtrate was diluted with DCM and washed with water. The organic layer was concentrated, and the crude compound used for next step without further purification. Nine hundred (900) mg of colorless liquid was obtained (giving a yield of about 89%).

[0124] Next, Na2COs (0.343g, 3.3 mmol) followed by Iodo propanol (1.15g) were added to the TSS precursor (1.5g, 2.7mm) in ACN (10 mL). The reaction mixture was stirred for 24h at 40°C. then filtration and filtrate were concentrated. The crude compound was washed with hexane two times to remove excess of iodo propanol to give about 1.1 g of pure surfactant in the form of a yellow liquid (giving a yield of about 52%).36DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOExample 8a: Determination of physical properties of Surfactant 8

[0125] The critical micelle concentration (CMC) for Surfactant 8 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 0.0773 mM (0.0526 mg / mL) at about pH 6. The plateau value of minimum surface tension that can be reached by this surfactant was about 21 .27 mN / m, indicating that the surfactant has outstanding interfacial activity. These results are plotted as surface tension versus concentration in Fig. 8. The molecular parameters of surfactant 8 are summarized below:Example 9: Synthesis of Surfactant 9Na2CO3, ACN1 .8 g, 93%

[0126] Synthesis procedure: Propyl amine (1.1 equiv.,) followed by Na2CO3 (1.5 equiv.,) were added to 1 g of starting material of bromo compound (2g, 1 equiv.,) in acetonitrile (25 mL) and the reaction mixture was stirred for 14h at 70°C temperature. After cooling the reaction mixture, it was filtered. The filtrate was then concentrated to be the crude compound that used for the next step. At this stage the crude compound was a 1 .8 g brown liquid (giving a yield of about 93% yield).DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WC

[0127] Next, D-Gluconic acid lactone (350 mg, 1 .96 mm) was added to the TSS precursor / crude compound (1g, 1.96 mm) in the MeOH (25mL), and the mixture was left for stirring at 70°C for 14h. After solvent was removed and the resulting substance washed with Diethyl ether, a crude compound of about 700 mg in the form of a sticky brown liquid was collected.Example 9a: Determination of physical properties of Surfactant 9

[0128] The critical micelle concentration (CMC) for Surfactant 9 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 0.0418 mM (0.0608 mg / mL) at about pH 6. The plateau value of minimum surface tension that can be reached by this surfactant was about 25.21 mN / m, indicating that the surfactant has outstanding interfacial activity. These results are plotted as surface tension versus concentration in Fig. 9. The molecular parameters of surfactant 9 are summarized below:Comparative Examples C1 - C338DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WC

[0129] Following the reaction scheme below, comparative examples were prepared, in essence, the two siloxane groups or “bis-version” of Surfactants 3 and 6 (Examples 3 and 6, above).Comparative Example C1 : Synthesis of Surfactant C1

[0130] Synthesis procedure: K2CO3 (2 equiv.,) followed by morpholine (1 equiv) were added to 1 g of starting material of bromo compound (1 equiv.,) in 50 mL of ACN at room temperature. The reaction mixture was then heated at 70°C for 14h. The reaction mixture was then filtered, the filtrate was then diluted with DCM and washed with water. The organic layer was then concentrated, and the crude compound used for next step without any further purification. At this point, the crude compound weighed about 0.95 g, and was in the form of a colorless liquid (giving a yield of about 94%)39DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WC

[0131] Synthesis procedure: Na2COs (1 equiv.,) followed by lodomethane (1.2 equiv) were added to 1 g of starting material of morpholine TSS substrate (1 equiv.,) in 30 mL of ACN at room temperature. The reaction mixture was then heated at 40°C for 14h. The reaction mixture was then filtered, the filtrate was concentrated, and the crude compound was washed with hexane. The compound was left to dry under high vacuum. About 0.8 g of brown semi solid was obtained (giving a yield of about 61 %).Comparative Example C1 : Determination of physical properties of Surfactant C1

[0132] The critical micelle concentration (CMC) for Surfactant C1 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 4.4611 mM (2.9680 mg / mL) at about pH 7. The plateau value of minimum surface tension that can be reached by this surfactant was about 20.83 mN / m. These results are plotted as surface tension versus concentration in Fig. 9. The results show the difficulty in predicting surfactant activity on the basis of chemical structure; Surfactant C1 , which differs only in the number of siloxane groups, displays moderate activity.Comparative Example C2: Synthesis of Surfactant C2

[0133] Synthesis procedure: K2CO3 (2 equiv.,) followed by piperidine (1 equiv) were added to 1 g of starting material of bromo compound (1 equiv.,) in 50 mL of ACN at room temperature, and the mixture was then heated at 70°C for 14h. The reaction mixture was then filtered, the filtrate was diluted with DCM and washed with water. The organic layer was thereafter concentrated, and the crude compound used for next step without any further purification. At this point, the crude compound was in the form of a colorless liquid, in the amount of about 0.93 g (giving a yield of about 92%).40DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0134] Na2COs (1 equiv.,) followed by lodomethane (1.2 equiv) were added to 1 g of starting material of piperidine TSS substrate (1 equiv.,) in 30 mL of ACN at room temperature, and the mixture was then heated at 40°C for 14h. The reaction mixture was then filtered, the filtrate was concentrated, and the crude compound was washed with hexane. The compound was then left to dry under high vacuum. The product was a brown sticky solid, in an amount of about 0.7 g (giving a yield of about 65%).Comparative Example C2: Determination of physical properties of Surfactant C2

[0135] The critical micelle concentration (CMC) for Surfactant C2 was measured. From the surface tension change with concentration in water, the CMC was determined to be about 4.2 mmol. The plateau value of minimum surface tension that can be reached by this surfactant was about 20.41 mN / m. These results are plotted as surface tension versus concentration in Fig. 10. The results show the difficulty in predicting surfactant activity on the basis of chemical structure; Surfactant C2, which differs only in the number of siloaxane groups, while displaying a low CMC and other surface activities, has rather poor wetting capability and lack-luster spreadabilty.Comparative Example C3:

[0136] Spreadability and wettability was further evaluated in comparison to 2,2,4-trimethyl-4-[(trimethylsilyl)oxy]-3,8, 11 -trioxa-2,4-disiladodecane having the molecular Formula ■ Ci3H34O4Si3; CAS Number ■ 27306-78-1 and molecular weight 338.666 g / mol, commercially available under the tradename Silwet-77®, which was obtained from Fisher Scientific. Silwet-77®, having the chemical structure shown below, is known of its excellent spreading and wetting properties.41DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOWetting and Spreading Comparison

[0137] The surfactants disclosed herein were compared to C3 with respect to spreading and wetting properties as follows. To evaluate the spreading and wetting behavior, a droplet of each was placed on a glass slide, representing a hydrophilic surface, and on a parafilm, representing a hydrophobic surface. The spreading behavior was observed visually, i.e., did the liguid tend to spread out, forming a flatter droplet, or did the liguid tend to “ball up.” Based on that, the surfactants were rated as “good wetting” (droplet completely flattened) “moderate wetting” (a flatter droplet) and “poor wetting” (droplet remains in a ball I as placed on surface). C1 shows super spreadability and wettability. The term “super wetting” is known in the art and refers to a liguid’s ability to spread rapidly and extensively over a surface, resulting in a low contact angle. As used herein, the term “super wetting” may be used herein interchangeably with “good wetting”.

[0138] Once each droplet is placed on a glass slide, there may be a spreading time during which the droplet is allowed to spread over the surface. The typical duration of this spreading time can range from a few seconds to several minutes. For good wetting” surfactants and compatible surfaces, spreading may occur within seconds. For “moderately wetting” surfactants, it may take from 30 seconds to 2 minutes. For “poor wetting”, it may take 2 minutes or more.

[0139] A schematic of spreading behavior is illustrated in Fig. 13. As shown therein, three separate liguid droplets, 12, 14, and 16 are contact with solid surface 10. The contact angle, represented by the symbol 9, is the angle formed between the tangent to the liguid droplet at the contact point and the solid surface 10. A contact angle of greater than 90°, shown by droplet 12, indicates poor wetting. A contact angle of approximately 90°, shown by droplet 14, indicates moderate wetting. A42DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO contact angle of less than 90°, shown by droplet 16, indicates super wetting. As noted above, the shape of the droplet flattens as its wetting ability improves.

[0140] Powder wetting properties were measured using a methodology as published in the literature, for example, in Colloids and Surfaces, 44(1990) 281-297, which involves a rough, qualitative measure to determine the effects of the synthesized surfactants on improving wetting of a polyethylene powder (PP) that would not, under typical circumstances, wet readily when placed atop a surface of distilled water. A small spatula-full of polyethylene powder (approximately 0.5 gram) was added to a water solution of a given surfactant at a concentration of 0.1 % wt / v. The speed at which the edge of the small pile of polyethylene initially atop the solution was noted, as well as the approximate length of time it takes to wet the powder completely. The same concentration, i.e., about 0.1 % wt.% of a surfactant solution was used to perform a qualitative determination of spreadabiity of surfactants atop of a paraffin film. The roundness (and also flatness) of the droplets containing surfactants atop the film is used as a measure to determine the spreadability, as depicted in Fig. 13.

[0141] TABLE 2 - Spreadability I Wetting Comparison of Surfactants 1 - 9 to C1 (exhibiting super wetting and spreading).

[0142] Table 3 shows a comparison of spreading and wetting properties of surfactants 3 and 6 versus surfactants from comparison examples C1 and C2, the 2- siloxane group containing version of surfactants 3 and 6.43DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WC

[0143] TABLE 3 - Spreadability / Wetting Comparison.

[0144] It was surprisingly found that cationic surfactants 3 and 6 show both, super wettability and super spreadability, whereas their counterpart bis-version of the compounds while indicating similar CMC levels do not demonstrate such superior, useful properties.

[0145] TABLE 4 Spreadability / Wetting Comparison to C3.

[0146] From the results above, it can be seen that small structural and molecular differences between compounds may lead to vastly and substantively different surfactant properties, such that that the wetting and spreading properties are not predictable simply from the presence of TSS groups. Though in some surfactants the presence of TSS groups at the end of the molecules confer great surfactant properties, that is not always the case. Indeed, surfactant properties are not predictable from the presence or the number of TSS groups present. Also, the44DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO presence of two as opposed to three TSS groups at one end of a surfactant molecule, such as in the case of Silwet-77®, may well render the surfactant molecule more structurally stable, because of the lower level of special obstruction in the case of two TSS groups. This higher structural stability is often thought to make the surfactant a better and more effective one in use. However, each of the surfactants of the present disclosure with three TSS groups at one end of the molecules has shown markedly improved surfactant functionality than its two-TSS counterpart, especially when it comes to wetting and spreading performances, which are key performance features of surfactants. Without wishing to be bound to any particular theory, Applicants suggest that the TSS end must be structurally “balanced” with the rest of the molecule to allow the molecule to have the right dynamic at a surface to move and spread and wet it. As such, a three-TSS group molecule, even one with not as low surface tension and CMC measures, may nevertheless have superior wetting and spreading properties, when compared to an otherwise similar molecule having two, one or no TSS groups.Antimicrobial Properties

[0147] The antimicrobial properties of surfactants can be examined using known methods and standard protocols, and various types of microorganisms as treatment targets. As a general matter, standard protocols can be developed to assess antimicrobial minimum inhibitory concentration (MIC) using serial dilution method, giving concentration-dependent microorganism growth inhibition measurements against gram positive (e.g., Streptococcus mutans, which is anaerobic, and Staphylococcus aureus, which is usually aerobic but can grow also anaerobically), gram negative (e.g., Escncnoc / a co / . which is anaerobic, or Psudomonas aeruginosa, which is aerobic).

[0148] Bacteria are propagated overnight in a suitable growth medium, e.g., a Tryptic Soy Broth. Prior to testing, the concentrations of the test organisms are established by measuring optical density using a spectrophotometer. Those bacterial samples are then diluted to about 1 E3 to 1 E4 CFU / mL. Thereafter, 10 pL of the bacterial cultures thus prepared are inoculated into test wells of a 96-well plate, each containing suitable growth media, for example, a Tryptic Soy Agar, and45DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO once the bacterial cultures are inoculated, these wells are then treated with the test specimen, serially diluted and are incubated at a temperature of 37 + / - 1°C and relative humidity of not less than 90% for about 24 + / - 1 hour.

[0149] Test surfactants are prepared into dilution series. All dilutions are conducted serially using a multichannel pipetter into 96-well microtiter plates. The dilution series are typically established by range-finding exercises so as to determine a high concentration ceiling and a series of diluted, lower concentrations so as to ensure that the test substance would at no time completely inhibit bacterial growth but still show effects.

[0150] The MIC is used to determine the approximate concentration of the test surfactant at which there is inhibition of bacterial growth.

[0151] A reference substance is typically used as a positive control in this antimicrobial testing protocol. For example, ADBAC Quarternary Amine having a CAS number of 139-08-2 would be a suitable test reference.

[0152] Test measurements are conducted on replicate 96-well plates, and reported as the rounded whole number average of the determined MIC. Replicate data are averaged by determination of the mean value (arithmetic average) for a selected measure using the equation: Arithmetic mean = the sum of the numbers in the set of interest / the number of terms. Measurement variability is then reported based on the determined average in the form of MIC + / -.ASPECTS

[0153] The subject matter encompassed by the following numbered aspects also forms part of the present disclosure, optionally in combination with the subject matter described above and / or defined in the claims that follow.

[0154] Aspect 1 A compound of Formula I or a salt thereof, below:Formula I46DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO wherein Y is selected from formula (A), (B) or (C)©Rthe wave-line denoting the connection to Formula I, whereinR1and R2are linked or otherwise connected together to form a ring that may be substituted or unsubstituted, saturated or unsaturated; optionally the ring may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms at any suitable position on the ring, and the ring may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; wherein the ring formed from R1and R2is optionally linked and / or fused to a further ring;R4and R5may be the same or different from one another, and comprise at least one group selected from the group consisting of Ci-Ce alkyl, optionally the Ci-Ce alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and wherein at least one alkyl chain is substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R3is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur;R6is optionally present and, if present, is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur; and an optional counterion may be associated with (C) and, if present, the47DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO counterion may be selected from the group consisting of chloride, bromide, and iodide; n is an integer from 1 to 12; andX is selected from the group consisting of chloride, bromide, and iodide.

[0155] Aspect 2 is the compound of Aspect 1 where Y is selected from piperidine, pyridine, pyrimidine, pyrrole, imidazole, pyrazole, piperazine, or morpholine.

[0156] Aspect 3 is the compound of Aspect 1 where Y is where Y isZ is O, NR7or CR8n and R3is as defined for Aspect 1 ;R7is hydrogen or Ci-Ce alkyl; andR8is hydrogen or Ci-Ce alkyl.

[0157] Aspect 4 is the compound of any one of Aspects 1 to 3 where R3is oxygen.

[0158] Aspect 5 is the compound of any one of Aspects 1 to 3 where R3is Ci-Ce alkyl.

[0159] Aspect 6 is the compound of any one of Aspects 1 to 3 where R3is Ci-Ce alkyl substituted with hydroxy.

[0160] Aspect 7 is the compound of any one of Aspects 3 to 6 where R7is methyl.

[0161] Aspect 8 is the compound of any of Aspects 3 to 7 where R8is hydrogen.

[0162] Aspect 9 is the compound of Aspect 1 , wherein Y is 4— N:R5R(C) the wave-line denoting the connection to Formula I,48DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WCR4and R5may be the same or different from one another, and comprise at least one group selected from the group consisting of Ci-Ce alkyl substituted with one or more substituents selected from the group consisting of hydroxyl and carbonyl,R6is selected from the group consisting of Ci-Ce alkyl, and the counterion is present and is iodide.

[0163] Aspect 10 is the compound of any one of Aspects 1 to 9 where Y is selected from

[0164] Aspect 11 is the compound of any one of Aspects 1 to 10 where n is 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0165] Aspect 12 is the compound of Aspect 11 where n is 5.

[0166] Aspect 13 is the compound of any of Aspects 1 to 12, where R3is methyl.

[0167] Aspect 14 is the compound of any of Aspects 1 to 12 wherein R3is oxygen.

[0168] Aspect 15 is the compound of any of Aspects 1 to 12 wherein R3is Ci- Ce alkyl, optionally substituted with hydroxyl.

[0169] Aspect 16 is the compound of any of Aspects 1 , 9 and 11 to 12, where R6is methyl.

[0170] Aspect 17 is the compound of any of Aspects 1 to 16, where the counterion is present and is selected from the group consisting of chloride, bromide, and iodide.49DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0171] Aspect 18 is the compound of any of Aspects 1 to 17, wherein the counterion is chloride.

[0172] Aspect 19 is the compound of any of Aspects 1 to 17, wherein the counterion is iodide.

[0173] Aspect 20 is the compound of any one of Aspects 1-19, wherein the compound is 4-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3- yl)propyl)amino)-6-oxohexyl)morpholine 4-oxide; having the following formula:

[0174] Aspect 21 is the compound of any one of Aspects 1-19, wherein the compound is 4-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3- yl)propyl)amino)-6-oxohexyl)-4-(3-hydroxypropyl)morpholin-4-ium iodide; having the following formula:

[0175] Aspect 22 is the compound of any one of Aspects 1-19, wherein the compound is 4-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3- yl)propyl)amino)-6-oxohexyl)-4-methylmorpholin-4-ium iodide; having the following formula:50DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0176] Aspect 23 is the compound of any one of Aspects 1-19, wherein the compound is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3- yl)propyl)amino)-6-oxohexyl)piperidine 1 -oxide; having the following formula:

[0177] Aspect 24 is the compound of any one of Aspects 1-19, wherein the compound is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy) trisiloxan-3- yl)propyl)amino)-6-oxohexyl)-1-(3-hydroxypropyl)piperidin-1-ium iodide; having the following formula:

[0178] Aspect 25 is the compound of any one of Aspects 1-19, wherein the compound is 1 -(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3- yl)propyl)amino)-6-oxohexyl)-1-methylpiperidin-1-ium iodide; having the following formula:

[0179] Aspect 26 is the compound of any one of Aspects 1-19, wherein the compound is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy) trisiloxan-3- yl)propyl)amino)-6-oxohexyl)-1 ,4,4-trimethylpiperazine-1 ,4-diium iodide; having the following formula:51DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO

[0180] Aspect 27 is the compound of any one of Aspects 1-19, wherein the compound is 6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3- yl)propyl)amino)-N,N-bis(2-hydroxyethyl)-N-methyl-6-oxohexan-1-aminium iodide; having the following formula:

[0181] Aspect 28 is the compound of any one of Aspects 1-19, wherein the compound is (2R,3S,4S,5S)-N-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-2, 3,4,5, 6-pentahydroxy- N-propylhexanamide; having the following formula:

[0182] Aspect 29 is a method of synthesizing a compound of Formula I or a salt thereof:Formula I wherein Y is selected from formula (A), (B) or (C)52DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOthe wave-line denoting the connection to Formula I, whereinR1and R2are linked or otherwise connected together to form a ring that may be substituted or unsubstituted, saturated or unsaturated ; optionally the ring may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms at any suitable position on the ring, and the ring may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; wherein the ring formed from R1and R2is optionally linked and / or fused to a further ring;R4and R5may be the same or different from one another, and comprise at least one group selected from the group consisting of Ci-Ce alkyl, optionally the Ci-Ce alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and wherein at least one alkyl chain is substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R3is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur;R6is optionally present and, if present, is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur; and an optional counterion may be associated with (C) and, if present, the counterion may be selected from the group consisting of chloride, bromide, and iodide;53DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO n is an integer from 1 to 12; andX is selected from the group consisting of chloride, bromide, and iodide, the method comprising: opening a lactam ring to provide an amino acid having an N-terminus and a C-terminus; alkylating the N-terminus to provide a tertiary amine; reacting the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative; and a reacting the siloxane derivative.

[0183] Aspect 30 is the method of Aspect 29, wherein the lactam is caprolactam.

[0184] Aspect 31 is the method of Aspect 29 or 30, wherein in the first alkylation step, the tertiary amine is 6-(dimethylamino)hexanoic acid.

[0185] Aspect 32 is the method of any one of Aspects 29-31 , wherein in the second alkylation step, the N-terminus is alkylated with an alkylating agent selected from the group consisting of benzyl bromide, ethyl bromoacetate, allyl iodide, propargyl bromide, 1-bromo-2-(2-methoxyethoxy)ethane, bromo phosphonate, 3- iodopropanol, 3-bromopropanol, 2-iodoethanol, 2-bromoethanol, 6-bromohexanoic acid, and 1 ,3-dibromopropane.

[0186] Aspect 33 is a surfactant of Formula (I) as defined in any one of Aspects 1 to 28.

[0187] Aspect 34 is the use of a compound of Formula (I) as defined in any one of Aspects 1 to 28 as a surfactant.54DMS_US.372434284.1

Claims

PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOCLAIMS1 . A compound of Formula I or a salt thereof, below:Formula I wherein Y is selected from formula (A), (B) or (C)the wave-line denoting the connection to Formula I, whereinR1and R2are linked or otherwise connected together to form a ring that may be substituted or unsubstituted, saturated or unsaturated; optionally the ring may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms at any suitable position on the ring, and the ring may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; wherein the ring formed from R1and R2is optionally linked and / or fused to a further ring;R4and R5is the same or different from one another, and comprise at least one group selected from the group consisting of Ci-Ce alkyl, optionally the Ci- Ce alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and wherein at least one alkyl chain is55DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R3is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, Cs-Cs carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur;R6is optionally present and, if present, is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur; and an optional counterion may be associated with (C) and, if present, the counterion may be selected from the group consisting of chloride, bromide, and iodide; n is an integer from 1 to 12; andX is selected from the group consisting of chloride, bromide, and iodide.

2. The compound of claim 1 where Y is selected from piperidine, pyridine, pyrimidine, pyrrole, imidazole, pyrazole, piperazine, or morpholine.

3. The compound of claim 1 where Y is where Y isZ is O, NR7or CR8n and R3is as defined for Aspect 1 ;R7is hydrogen or Ci-Ce alkyl; andR8is hydrogen or Ci-Ce alkyl.

4. The compound of any one of claims 1 to 3 where R3is oxygen.

5. The compound of any one of claims 1 to 3 where R3is Ci-Ce alkyl or Ci-Ce alkyl.56DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO6. The compound of any one of claims 1 to 3 where R3is Ci-Ce alkyl substituted with hydroxy.

7. The compound of any one of claims 3 to 6 where R7is methyl.

8. The compound of any of claims 3 to 7 where R8is hydrogen.

9. The compound of claim 1 , wherein Y isthe wave-line denoting the connection to Formula I,R4and R5may be the same or different from one another, and comprise at least one group selected from the group consisting of Ci-Ce alkyl substituted with one or more substituents selected from the group consisting of hydroxyl and carbonyl; andR6is selected from the group consisting of Ci-Ce alkyl.

10. The compound of any one of claims 1 to 9 where Y is selected from11 . The compound of any one of claims 1 to 10 where n is 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

12. The compound of claim 11 where n is 5.57DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO13. The compound of any of claims 1 to 12, where R3is methyl.

14. The compound of any of claims 1 to 12 wherein R3is oxygen.

15. The compound of any of claims 1 to 12 wherein R3is Ci -Ce alkyl, optionally substituted with hydroxyl.

16. The compound of any of claims 1 , 9 and 11 to 12, where R6is methyl.

17. The compound of any of claims 1 to 16, where the counterion is present and is selected from the group consisting of chloride, bromide, and iodide.

18. The compound of any of claims 1 to 17, wherein the counterion is chloride.

19. The compound of any of claims 1 to 17, wherein the counterion is iodide.

20. The compound of any one of claims 1 -19, wherein the compound is 4-(6-((3- (1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6- oxohexyl)morpholine 4-oxide; having the following formula:21 . The compound of any one of claims 1 -19, wherein the compound is 4-(6-((3- (1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6- oxohexyl)-4-(3-hydroxypropyl)morpholin-4-ium iodide; having the following formula:58DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO22. The compound of any one of claims 1-19, wherein the compound is 4-(6-((3- (1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6- oxohexyl)-4-methylmorpholin-4-ium iodide; having the following formula:

23. The compound of any one of claims 1-19, wherein the compound is 1-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6- oxohexyl)piperidine 1 -oxide; having the following formula:

24. The compound of any one of claims 1-19, wherein the compound is 1-(6-((3- (1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy) trisiloxan-3-yl)propyl)amino)-6- oxohexyl)-1-(3-hydroxypropyl)piperidin-1-ium iodide; having the following formula:

25. The compound of any one of claims 1-19, wherein the compound is 1-(6-((3- (1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6- oxohexyl)-1-methylpiperidin-1-ium iodide; having the following formula:59DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO26. The compound of any one of claims 1 -19, wherein the compound is 1-(6-((3- (1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy) trisiloxan-3-yl)propyl)amino)-6- oxohexyl)-1 ,4,4-trimethylpiperazine-1 ,4-diium iodide; having the following formula:

27. The compound of any one of claims 1 -19, wherein the compound is 6-((3- (1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)- N,N-bis(2-hydroxyethyl)-N-methyl-6-oxohexan-1 -aminium iodide; having the following formula:

28. The compound of any one of claims 1 -19, wherein the compound is (2R,3S,4S,5S)-N-(6-((3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)-2,3,4,5,6- pentahydroxy-N-propylhexanamide; having the following formula:

29. A method of synthesizing a compound of Formula I or a salt thereof:60DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WOFormula I wherein Y is selected from formula (A), (B) or (C)the wave-line denoting the connection to Formula I, whereinR1and R2are linked or otherwise connected together to form a ring that may be substituted or unsubstituted, saturated or unsaturated ; optionally the ring may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms at any suitable position on the ring, and the ring may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; wherein the ring formed from R1and R2is optionally linked and / or fused to a further ring;R4and R5are the same or different from one another, and comprise at least one group selected from the group consisting of Ci-Ce alkyl, optionally the Ci- Ce alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and wherein at least one alkyl chain is substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R3is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur;R6is optionally present and, if present, is selected from the group consisting of alkyl, alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxy alkyl ether, alkyl61DMS_US.372434284.1PCT / US25 / 40309 01 August 2025 (01.08.2025)A600098-WO phosphate, Cs-Cs carboxylic acid, C1-C10 alkyl benzoic acid, oxygen, and sulfur; and an optional counterion may be associated with (C) and, if present, the counterion may be selected from the group consisting of chloride, bromide, and iodide; n is an integer from 1 to 12; andX is selected from the group consisting of chloride, bromide, and iodide, the method comprising: opening a lactam ring to provide an amino acid having an N-terminus and a C-terminus; alkylating the N-terminus to provide a tertiary amine; reacting the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative; and a reacting the siloxane derivative.

30. The method of claim 29, wherein the lactam is caprolactam.31 . The method of claim 29 or 30, wherein in the first alkylation step, the tertiary amine is 6-(dimethylamino)hexanoic acid.

32. The method of any one of claims 29-31 , wherein in the second alkylation step, the N-terminus is alkylated with an alkylating agent selected from the group consisting of benzyl bromide, ethyl bromoacetate, allyl iodide, propargyl bromide, 1 -bromo-2-(2-methoxyethoxy)ethane, bromo phosphonate, 3- iodopropanol, 3-bromopropanol, 2-iodoethanol, 2-bromoethanol, 6- bromohexanoic acid, and 1 ,3-dibromopropane.

33. A surfactant of Formula (I) as defined in any one of claims 1 to 28.

34. The use of a compound of Formula (I) as defined in any one of claims 1 to 28 as a surfactant.62DMS_US.372434284.1

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