Surfactants for inks, coatings and adhesives

Abstract

Inks, coatings, adhesives, and paint removers may be formulated to include one or more surfactants from one or more surfactant classes, such as siloxane derivatives of amino acids having surface active properties.

Description

Surfactants used in inks, coatings, and adhesives

[0001] Cross-reference to related applications This application claims priority to U.S. Patent Application No. 18 / 795,167, filed August 5, 2024, which claims priority to U.S. Provisional Patent Application No. 63 / 531,200, filed August 7, 2023, the entire disclosure of which is incorporated herein by reference. Technical Field

[0002] This disclosure relates to surfactants for use in inks, coatings, and adhesives. Such surfactants may comprise siloxane derivatives of amino acids, wherein the siloxane derivatives have surface-active properties. Background Technology

[0003] Surfactants (molecules with surface-active properties) are widely used in commercial formulations of inks, coatings, adhesives, and paint removers. Surfactants can be included as emulsifiers, wetting agents, foaming agents, dispersants, and / or agents that improve spreadability.

[0004] Surfactants can be uncharged, amphoteric, cationic, or anionic. Although in principle any class of surfactant (e.g., cationic, anionic, nonionic, amphoteric) is applicable, formulations may contain combinations of two or more surfactants from two or more surfactant classes.

[0005] Typically, surfactants are amphiphilic molecules with a relatively water-insoluble hydrophobic "tail" group and a relatively water-soluble hydrophilic "head" group. These compounds can adsorb at interfaces, such as between two liquids, a liquid and a gas, or a liquid and a solid. In systems containing relatively polar and relatively nonpolar components, the hydrophobic tail preferentially interacts with one or more of the relatively nonpolar components, while the hydrophilic head preferentially interacts with one or more of the relatively polar components. In the case of a water-oil interface, the hydrophilic head group preferentially extends into the water, while the hydrophobic tail preferentially extends into the oil. When added to a water-gas interface, the hydrophilic head group preferentially extends into the water, while the hydrophobic tail preferentially extends into the gas. The presence of surfactants disrupts at least some of the intermolecular interactions between water molecules, replacing at least some of the normally weaker interactions between water molecules and the surfactant. This results in a reduction in surface tension and can also be used to stabilize interfaces.

[0006] At sufficiently high concentrations, surfactants can form aggregates that confine the hydrophobic tails to the polar solvent. One such aggregate is a micelle. In a typical micelle, molecules are arranged in a sphere, with the hydrophobic tails of one or more surfactants preferably located within the sphere, and the hydrophilic heads of one or more surfactants preferably located on the outside of the micelle, where the heads preferably interact with the more polar solvent. The effect of the given compound on surface tension and its concentration at which micelles form can serve as a defining characteristic of the surfactant. Summary of the Invention

[0007] This disclosure provides formulations of inks, coatings, adhesives, and paint removers. These products can be formulated to contain one or more surfactants from one or more surfactant classes disclosed herein. Surfactants can be used as emulsifiers, wetting agents, dispersants, and / or agents that improve spreadability.

[0008] This disclosure provides surfactants for coatings, inks, adhesives, and paint removers in the form of amino acid siloxane derivatives with surface-active properties. The amino acids can be naturally occurring or synthetic, or they can be obtained via ring-opening reactions of molecules such as lactams (e.g., caprolactam). The amino acids can be functionalized with different types of siloxane groups to form compounds with surface-active properties. Characteristically, these compounds may have a low critical micelle concentration (CMC) and / or the ability to reduce the surface tension of liquids.

[0009] This disclosure provides formulations for use in ink fixing solutions, comprising one or more surfactant molecules having a structure of formula I or II. Formula I Equation II, where R 1 and R 2 They may be the same or different, and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylic acid esters; R 3 Selectable from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12The linker is connected to another surfactant molecule having the structure shown in Formula I, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chloride ions, bromide ions, and iodide ions; optionally, one or more wetting agents, metal carboxylates as fixing agents, and acids.

[0010] The formulation may also include an aqueous carrier and one or more colorants dispersed in the ink carrier.

[0011] For clarity, as disclosed herein, and for any formulation provided herein, a molecule of Formula II may represent a construct with the following structure: Formula I - Linker - Formula I, wherein a molecule of Formula I may be the same as or different from another molecule of Formula I. In this exemplary construct, the linker is R in Formula I. 3 That is, C1-C 12 Connecting base.

[0012] Other surfactant molecules provided in this disclosure are those compounds of formula I or II, wherein R 1 and R 2 It is a methyl group.

[0013] Other surfactant molecules provided in this disclosure are compounds of formula I or II, wherein n and / or z is 5.

[0014] Specifically, R 3 Optional from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkages attached to the second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0015] More specifically, R 3 The following formula can be selected: .

[0016] The use of compounds of formula I or II described herein as surfactants in ink fixer formulations described herein is also disclosed.

[0017] This disclosure further provides formulations for coatings comprising one or more surfactant molecules having a structure of formula I or II. Formula I Equation II, where R1 and R 2 They may be the same or different, and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylic acid esters; R 3 Selectable from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to another surfactant molecule having the structure shown in Formula I, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chloride ions, bromide ions, and iodide ions; optionally, latex, adhesive, one or more desiccants, one or more pigments, one or more solvents, and water.

[0018] Specifically, R 3 Optional from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkages attached to the second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0019] More specifically, R 3 The following formula can be selected: .

[0020] The use of compounds of formula I or II described herein as surfactants in the coating formulations described herein is also disclosed.

[0021] This disclosure also provides formulations for adhesives comprising one or more surfactant molecules having a structure of formula I or II. Formula I Equation II, where R 1 and R 2They may be the same or different, and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylic acid esters; R 3 Selectable from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to another surfactant molecule having the structure shown in Formula I, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chloride ions, bromide ions, and iodide ions; optionally, a resin, one or more fillers, and a solvent.

[0022] Specifically, R 3 Optional from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkages attached to the second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0023] More specifically, R 3 The following formula can be selected: .

[0024] The use of compounds of formula I or II described herein as surfactants in adhesive formulations described herein is also disclosed.

[0025] This disclosure also provides formulations for paint removers comprising one or more surfactant molecules having a structure of formula I or II. Formula I Equation II, where R 1 and R 2They may be the same or different, and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylic acid esters; R 3 Selectable from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to another surfactant molecule having the structure shown in Formula I, wherein the other surfactant molecule of Formula I may be the same as or different from the surfactant molecule of Formula I; n and z may be independently selected from any integer from 1 to 12; m may be any integer from 1 to 12; and X may be selected from chloride ions, bromide ions, and iodide ions; optionally, dichloroethylene; one or more cosolvents; corrosion inhibitors; waxes; thickeners; and water.

[0026] Specifically, R 3 Optional from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkages attached to the second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0027] More specifically, R 3 The following formula can be selected: .

[0028] The use of compounds of formula I or II described herein as surfactants in paint remover formulations described herein is also disclosed.

[0029] The above and other features of this disclosure, and the ways in which they are implemented, will become more apparent and will be better understood by referring to the following description of the embodiments in conjunction with the accompanying drawings. Attached Figure Description

[0030] Figure 1 shows a graph of the surface tension of surfactant 1 as described in Example 2b, relative to its concentration.

[0031] Figure 2 shows a graph of the surface tension of surfactant 2 as described in Example 3b, relative to its concentration.

[0032] Figure 3 shows a graph of the surface tension of surfactant 3 as described in Example 4b, relative to its concentration.

[0033] Figure 4 shows a graph of the surface tension of surfactant 4 as described in Example 5b, relative to its concentration.

[0034] Figure 5 shows a graph of the surface tension of surfactant 5 as described in Example 6b, relative to its concentration.

[0035] Figure 6 shows a graph of the surface tension of surfactant 6 as described in Example 7b, relative to its concentration.

[0036] Figure 7 shows a graph of the surface tension of surfactant 7 as described in Example 8b, relative to its concentration.

[0037] Figure 8 shows a graph of the surface tension of surfactant 8 as described in Example 9b, relative to its concentration.

[0038] Figure 9 shows a graph of the surface tension of surfactant 9 as described in Example 11b, relative to its concentration.

[0039] Figure 10 shows a graph of the surface tension of surfactant 10 as described in Example 10b, relative to its concentration.

[0040] Figure 11 shows a graph of the surface tension of the surfactant as described in Comparative Example A2 relative to its concentration. Detailed Implementation

[0041] The phrase “within any range using these endpoints” as used in this article literally means any range of values ​​that can be selected from any two values ​​listed before this phrase, whether those values ​​are in the lower or higher part of the list. For example, a pair of values ​​can be selected from two lower values, two higher values, or a lower value and a higher value.

[0042] As used in this article, the term "alkyl" refers to any saturated carbon chain, which can be straight or branched, and can be substituted at any position along the carbon chain. The carbon chain can have 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbons.

[0043] As used herein, the phrase "surfactant" refers to the ability of a compound to reduce the surface tension of the medium in which it is at least partially dissolved and / or the interfacial tension with other phases, and thus to be at least partially adsorbed at liquid / vapor and / or other interfaces. The term "surfactant" can be applied to such compounds.

[0044] Regarding the terminology of imprecision, the terms "approximately" and "roughly" are used interchangeably to refer to a measurement that includes the measured value and any measurement that is substantially close to the measured value. As understood and readily determined by one of ordinary skill in the art, a measurement that is substantially close to the measured value differs from the measured value by a considerably small amount. Such deviations may be attributed to measurement errors or minor adjustments made to optimize performance. In cases where the value of such a considerably small difference would not be readily discernible to one of ordinary skill in the art, the terms "approximately" and "roughly" can be understood to mean ±15% of the value, such as ±15%, ±12%, ±10%, ±9%, ±8%, ±8%, ±7%, ±6%, ±5%, ±4%, ±3%, ±2%, or even ±1%, etc.

[0045] This disclosure provides formulations of inks, coatings, adhesives, and paint removers.

[0046] I. Several reasons have made inkjet printing a popular method for recording images on various media surfaces, especially paper. Some of these reasons include low printer noise, high-speed recording capabilities, high quality, and multi-color recording. Additionally, these advantages are available to consumers at a relatively low price. However, despite significant improvements in inkjet printing, consumer demands in this field are increasing, such as higher speeds, higher resolution, full-color image formation, increased stability, and more durable images.

[0047] Inkjet ink kits are used in color inkjet printing systems. An ink kit typically includes multiple inks of different colors, usually in sets of four, six, or eight colors (e.g., one or more shades of cyan, magenta, yellow, and / or black), and may also include image fixing / fixer fluid. Fixer fluid is typically applied before or after the inks are applied to the surface of the printing media. Fixer fluid is a substantially colorless liquid that interacts with the colorant and / or polymer components of one or more inks, thereby depositing or otherwise fixing one or more inks onto the surface of the printing media.

[0048] The precipitated colorant deposits on the surface of the medium, resulting in enhanced image quality properties such as optical density and chromaticity. Durability properties such as water resistance and highlighter stain resistance also benefit from this active ink chemistry. Although several suitable ink kits including fixer are currently available, improvements are expected to formulate more durable and reliable inks that will produce higher quality printed images on the surface of the printing medium without damaging the printhead containing it. Unbound by any theory, it is believed that after the fixer composition is overprinted with the inkjet ink composition onto the substrate, or in other words, when the ink and fixer meet on the medium surface, a very efficient collision of ink colorants is achieved, and almost all the colorant is deposited on the surface of the medium, rather than penetrating the medium and depositing below the surface. Simultaneously, the fixer carrier becomes highly wetted after mixing with the ink carrier, and the mixed carrier rapidly penetrates the medium, leaving the colorant behind.

[0049] In this inkjet printing method, the combination of fixer and inkjet ink composition produces a system and method that provides high-quality and durable inkjet image printing. The use of the fixer disclosed herein results in enhanced image quality properties such as optical density, chromaticity, and durability. Furthermore, when used in an inkjet printing system, the fixer composition provides good image quality without adversely affecting the reliability of the inkjet structure. In fact, it has been found that the fixer does not damage the printhead containing it and exhibits low corrosivity to the inkjet system and inkjet pen.

[0050] The ink formulation disclosed herein comprises an inkjet fixing composition comprising one or more surfactants selected from one or more surfactant classes, one or more wetting agents, a metal carboxylate as a fixing agent, and an acid, based on adjusting the pH of the composition to about 5.0 to about 7.0. The formulation may also be an aqueous carrier and one or more colorants dispersed in the ink carrier.

[0051] 1. Surfactants The ink formulations of this disclosure comprise one or more surfactants, also referred to as surfactant systems. Surfactants have an excellent ability to maintain surface tension and interfacial tension at appropriate levels. Surfactants can also be used as wetting agents and dispersants. Suitable surfactants for use in the ink formulations of this disclosure comprise one or more surfactants of formula I or II and / or co-surfactants. Formula I Equation II, where R 1 and R 2They may be the same or different, and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylic acid esters; R 3 Selectable from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to another surfactant molecule having the structure shown in Formula I, wherein the other surfactant molecule of Formula I may be the same as or different from the surfactant molecule of Formula I; n and z may be independently selected from any integer from 1 to 12; m may be any integer from 1 to 12; and X may be selected from chloride ions, bromide ions, and iodide ions.

[0052] Specifically, R 3 Optional from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkages attached to the second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0053] More specifically, R 3 The following formula can be selected: .

[0054] In particular, suitable surfactants or co-surfactants may include any one of the surfactants 1-12 described herein.

[0055] The amount of surfactant system in the ink formulation, based on the weight of the composition, may be in the range of about 0% by weight or more, about 0.1% by weight or more, about 0.2% by weight or more, about 0.4% by weight or more, about 0.6% by weight or more, about 0.8% by weight or more, or about 1.0% by weight or less, about 1.2% by weight or less, about 1.4% by weight or less, about 1.6% by weight or less, about 1.8% by weight or less, or about 2.0% by weight or less, or in any range from 0% by weight to 2% by weight, or from 0.1% by weight to 1.8% by weight, or from 0.2% by weight to 1.6% by weight, or from 0.4% by weight to 1.4% by weight, or from 1.0% by weight to 1.2% by weight, or in any range using any two of the foregoing values.

[0056] 2. Wetting Agent The ink formulations disclosed herein contain a wetting agent. "Wetting agent" herein refers to any substance used as a wetting agent or humectant. Without any theoretical connection, the wetting agent maintains the water content of the fixer within a narrow range, independent of humidity fluctuations, and is therefore typically added to prevent clogging of narrow inkjet pen nozzles.

[0057] Wetting agents are high-boiling-point water-miscible organic compounds, such as polyols, amides, or polyethers. Wetting agents can be water-soluble. Suitable water-soluble wetting agents for this purpose include, but are not limited to, heterocyclic ketones (e.g., 2-pyrrolidone, N-methylpyrrolidone-2-one, 1,3-dimethylimidazolidine-2-one, octylpyrrolidone, etc.); diols (e.g., ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, etc.); glycerol; and diols (e.g., butanediol, pentanediol, hexanediol, etc.).

[0058] The wetting agent may be present in the ink formulation in an amount of about 1% or more, 2% or more, 5% or more, 8% or more, or 10% or less, 12% or less, 15% or less, 18% or less, 20% or less, or in any range using these endpoints.

[0059] 3. Fixing fluid, also known as fixing agent, contains an aqueous carrier and an effective amount of one or more fixing agents. A fixing agent is a component that induces a change in the solubility or stability of the colorant and fixes the colorant to the appropriate location in the printed image. The "effective amount" of fixing agent is the amount that effectively improves print quality compared to an unfixed print, such as reduced bleed and show-through, increased optical density (OD), chromaticity, edge sharpness, and improved drip and smear fastness. Fixing fluids can be formulated for high spreadability and rapid penetration and drying. Surface tension can be less than about 45 mN / m.

[0060] Fixing agents can be metal carboxylates, such as metal salts composed of polyvalent metal ions and carboxylate ions.

[0061] Suitable metal carboxylates may include polyvalent metal carboxylates, which contain divalent metal ions such as Ca. 2+ Mg 2 + Cu 2+ and trivalent metal ions such as Al 3+ La 3+ or Fe 3+ .

[0062] Carboxylate ions can be aliphatic monocarboxylic acids with 1-6 carbon atoms. Suitable carboxylate ions include acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, neovaleric acid, and hexanoic acid.

[0063] The fixer is present in the fixer composition in amounts of about 3% or more by weight, about 4% or more by weight, about 5% or more by weight, about 6% or more by weight, about 7% or more by weight, about 8% or more by weight, about 9% or more by weight, or about 10% or less by weight, about 11% or less by weight, about 12% or less by weight, about 13% or less by weight, about 14% or less by weight, about 15% or less by weight, about 16% or less by weight, or in any range using these endpoints.

[0064] 4. The acid fixer may include an acid. Any suitable acid may be selected. For example, a strong acid (i.e., an acid that is completely ionized in water) may be added to the fixer composition. Non-limiting examples of such acids include methanesulfonic acid, hydrochloric acid, nitric acid, hydrobromic acid, sulfuric acid, perchloric acid, hydroiodic acid, trifluoroacetic acid, and / or combinations thereof.

[0065] Acids help to adjust the pH of the fixer composition. The pH of the fixer composition can be about 5.0 or greater, about 5.5 or greater, about 6.0 or greater, about 6.5 or less, about 7.0 or less, or in any range using these endpoints.

[0066] In some respects, the fixer formulation will not form or will form less than 0.5% acid vapor (volatile organic acids) after assembly. In other respects, the pH of the fixer solution will be adjusted to a suitable range to avoid the fixer composition containing more than 0.5% by weight of volatile organic acids.

[0067] 5. Aqueous Formulations The fixing solutions disclosed herein may contain an aqueous carrier. As defined herein, the term "aqueous carrier" refers to an aqueous mixture in which the fixing agent is placed to form the fixing solution. Suitable aqueous carrier components may include, but are not limited to, water, cosolvents, surfactants, additives (corrosion inhibitors, salts, etc.), and / or combinations thereof.

[0068] The aqueous carrier may contain a water-soluble organic cosolvent, an additional surfactant, and water. Non-limiting examples of water-soluble organic cosolvents include 2-ethyl-2-hydroxymethyl-1,3-propanediol, glycerol propoxylate, tripropylene glycol, 1-(2-hydroxyethyl)-2-pyrrolidone, 1-(2-hydroxyethyl)-2-imidazolinone, and / or combinations thereof.

[0069] 6. Colorant The inkjet ink kit of this disclosure may include aspects of the fixer composition and an ink having a colorant dispersed or dissolved in an ink carrier. The inkjet ink kit may at least include an inkjet ink composition containing a colorant dispersed in an ink carrier, and a fixer containing one or more surfactants selected from one or more surfactant classes, one or more wetting agents, a metal carboxylate as a fixer, and an acid.

[0070] It should be understood that any number of colored ink compositions may be contained in an ink kit containing a fixer. Furthermore, any desired combination of colored inks may be used. For example, each colored ink composition may be a different color, or two or more inks may be different shades of the same color (i.e., light magenta and dark magenta inks). In some aspects, inkjet ink kits contain four different colors of ink: black ink, yellow ink, cyan ink, and magenta ink. In other aspects, inkjet ink kits contain any desired number of inks selected from black ink, yellow ink, cyan ink, magenta ink, orange ink, red ink, green ink, and / or combinations thereof. In some aspects, inkjet ink kits contain a fixer as described herein and contain inkjet ink compositions selected from black ink, yellow ink, cyan ink, magenta ink, orange ink, red ink, and green ink.

[0071] Each ink contains a colorant selected from pigments, dyes, or combinations thereof. In some embodiments, the ink contains a pigment as a colorant. As used herein, "pigment" refers to colorant particles that are substantially insoluble in the liquid carrier to which they are used. Pigments may be dispersed using a single dispersant or may be self-dispersible, having a dispersant attached to the pigment surface. As used herein, "self-dispersible" generally refers to a pigment that has been functionalized with a dispersant, for example, by chemically attaching the dispersant to the pigment surface. The dispersant may be a small molecule or a polymer or oligomer. Pigments comprise both self-dispersible pigments and dispersed pigments, such as pigments dispersed by a single dispersant non-covalently attached to the surface. In one instance, the pigment is not self-dispersible, and a dispersing aid may be incorporated into the carrier. In another instance, the pigment is self-dispersible and modified to contain at least one polymer chemically attached thereto.

[0072] In the example colorants, the numbers categorize the chemical composition, so "Pigment Blue 29" indicates that it is sodium aluminum sulfosilicate. These numbers are not directly related to any part of the actual chemical structure; rather, they are assigned according to the order in which the pigments were added to the general code of the color index (not according to when the pigments were discovered).

[0073] Colorants for cyan and / or magenta inks can be combinations of pigments and dyes. Pigments and / or dyes for cyan and magenta colorants can be selected from several commercially available pigments and / or dyes. Non-limiting examples of suitable pigments for cyan colorants include Pigment Blue 1, Pigment Blue 2, Pigment Blue 3, Pigment Blue 15:4, Pigment Blue 16, Pigment Blue 22, Pigment Blue 29, Vat Blue 4, Vat Blue 6 and / or similars, and / or combinations thereof. Examples of suitable dyes for cyan colorants include, but are not limited to, triphenylmethane dyes, such as, for example, Acid Blue 9 and Acid Blue 7, and phthalocyanine dyes, such as, for example, Direct Blue 199. Non-limiting examples of suitable pigments for magenta colorants include Pigment Red 5, Pigment Red 7, Pigment Red 12, Pigment Red 48, Pigment Red 57, Pigment Red 112, Pigment Red 122 and / or similars, and / or combinations thereof. Examples of dyes suitable for magenta colorants include, but are not limited to, xanthan dyes such as, for example, Acid Red 52, Acid Red 289, γ-acid dyes, H-acid dyes and / or combinations thereof.

[0074] Colorants used for black and / or yellow inks can be dyes or pigments. Examples of suitable dyes for black colorants include, but are not limited to, water-soluble metal complex azo dyes such as Reactive Black 31 and Reactive Black 8, water-soluble polyazo dyes such as Direct Black 19, Direct Black 195 and Direct Black 168, and water-soluble sulfur dyes such as Solubilized Sulfur Black 1. Materials such as carbon black or carbon black derivatives are non-limiting examples of suitable pigments for black inks.

[0075] Examples of suitable dyes for yellow colorants include, but are not limited to, AY-17, AY-23, DY-132, Y-104 and / or combinations thereof. PY-74 is a non-limiting example of a pigment suitable for yellow inks.

[0076] It should be understood that one or more inks in an ink kit may contain substantially the same colorant and / or substantially the same ink carrier formulation. In one example, the ink kit contains yellow ink, cyan ink, and magenta ink, each having substantially the same ink carrier formulation.

[0077] The amount of colorant present in each ink composition is about 2.7% by weight or more, about 2.9% by weight or more, about 3.0% by weight or more, about 3.2% by weight or more, about 3.4% by weight or more, or about 3.6% by weight or less, about 3.8% by weight or less, about 4.0% by weight or less, about 4.2% by weight or less, about 4.4% by weight or less, about 4.5% by weight or less, or within any range using these endpoints. However, it should be understood that the amount of colorant may be more or less than the above ranges depending on the application requirements.

[0078] 7. Other Additives One or more additives may also be incorporated into the fixer composition. As used herein, the term “additive” refers to a component of a fluid that operates to enhance the fluid’s performance, environmental effects, aesthetic effects, or other similar properties. Suitable additives include biocides, masking agents, chelating agents, corrosion inhibitors, marking dyes (e.g., visible light, ultraviolet light, infrared light, fluorescence, etc.) and / or combinations thereof. Fixers may contain corrosion inhibitors, such as Cobratec. ® CBT, carboxybenzotriazole, is available from PMC Specialties Group, Inc.

[0079] The additive is present in the fixing composition in an amount of about 0% by weight or more, about 0.01% by weight or more, about 0.1% by weight or more, about 0.2% by weight or more, about 0.3% by weight or more, about 0.4% by weight or more, or about 0.5% by weight or less, about 0.6% by weight or less, about 0.7% by weight or less, about 0.8% by weight or less, about 0.9% by weight or less, about 1% by weight or less, or any range using these endpoints. It should be understood that the upper limit of the amount of additive present depends at least in part on the additive used, its effect on the image, its solubility, its effect on pen function, and / or a combination thereof.

[0080] 8. Ink Carrier Each colorant or combination of colorants is combined with its respective individual ink carrier to form one or more inks in an ink kit. As defined herein, an "ink carrier" is a carrier in which colorants are placed to form ink. A wide variety of ink carriers can be used with inks, ink kits, and methods according to the embodiments disclosed herein. Non-limiting examples of suitable components for ink carriers include water-soluble polymers, anionic polymers, surfactants, solvents, cosolvents, buffers, biocides, masking agents, viscosity modifiers, chelating agents, resins, and / or water, and / or combinations thereof.

[0081] Suitable solvents for ink carriers include, but are not limited to, glycerol polyoxyethylene ether, tripropylene glycol, tetraethylene glycol, 1-(2-hydroxyethyl)-2-imidazolinone, 1-(2-hydroxyethyl)-2-pyrrolidone, 1,6-hexanediol, 1,2,6-hexanetriol, trimethylolpropane, dipropylene glycol, Dantocol® DHE (Lonza Inc., Fairlawn NJ), and / or combinations thereof. Inks used in combination with fixers may include one or more of the following solvents: ethylene glycol, diethylene glycol, triethylene glycol, or 1-propoxy-2-propanol.

[0082] The solvent may be present in the ink carrier in amounts of about 1% by weight or more, about 5% by weight or more, about 10% by weight or more, or about 15% by weight or less, about 20% by weight or less, about 25% by weight or less, or in any range using these endpoints.

[0083] The amount and type of solvent used depend, at least in part, on the desired properties of the ink. Therefore, the amount can vary as needed. In some respects, a single solvent is used in the ink carrier of one or more colored inks. Suitable solvents include, but are not limited to, tripropylene glycol, tetraethylene glycol, or 1-(2-hydroxyethyl)-2-pyrrolidone. In other respects, the ink comprises a mixture of two or more of the aforementioned solvents.

[0084] As a non-limiting example, cyan, magenta, yellow, and black inks contain a mixture of Dantocol® DHE and 1-(2-hydroxyethyl)-2-pyrrolidone. The total weight percentage of the solvent mixture may range from about 7% by weight or more, about 9% by weight or more, about 11% by weight or more, about 13% by weight or more, about 15% by weight or more, or about 17% by weight or less, about 19% by weight or less, about 21% by weight or less, about 22% by weight or less, or within any range using these endpoints.

[0085] Suitable surfactants include the surfactants disclosed herein and / or ethoxylated alcohols, fluorinated surfactants, 2-diethylene glycol surfactants, phosphate surfactants, diphosphate surfactants, alkyl sulfates, alkyl ether sulfates and / or combinations thereof.

[0086] The amount of one or more surfactants present in the ink carrier may be about 8% by weight or less, about 6% by weight or less, about 4% by weight or less, about 2% by weight or less, about 1% by weight or less, or about 0.1% by weight or less.

[0087] The ink carrier may contain at least one polymer. The polymer used for the ink carrier is typically water-soluble and may be selected from salts of styrene-(meth)acrylic acid copolymers, salts of polystyrene-acrylic acid polymers, salts of polyurethanes, and / or salts of other water-soluble polymeric binders and / or combinations thereof. Non-limiting examples of suitable polyurethanes include those commercially available from Dainippon Ink & Chem., Inc. (DIC), Osaka, Japan.

[0088] The polymer may be present in the ink carrier in amounts of about 0.01% by weight or more, about 0.1% by weight or more, about 0.5% by weight or more, about 1% by weight or more, or about 2% by weight or less, about 3% by weight or less, about 4% by weight or less, or in any range using these endpoints.

[0089] Additives may also be incorporated into the ink carrier of the ink in the embodiment. As a non-limiting example, a bactericide such as Proxel® GXL may be added to the ink to protect it from bacterial growth. Other suitable additives include, but are not limited to, buffers, biocides, masking agents, chelating agents, or combinations thereof.

[0090] The ink carrier contains one or more additives present in amounts of about 0% by weight or more, about 0.1% by weight or more, about 0.2% by weight or more, or about 0.3% by weight or less, about 0.4% by weight or less, about 0.5% by weight or less, or in any range using these endpoints.

[0091] 9. Preparation Method The ink formulation can be prepared by combining a solvent, a surfactant, one or more of any additives, and water, and adjusting the pH to an alkaline pH. In some embodiments, the pH range of the colored ink is from about 8 to about 11. In other embodiments, the pH range of the colored ink is from about 8.5 to about 9.5. A colorant and a polymer are then added to form the ink composition.

[0092] II. Coatings This disclosure provides coating formulations, particularly latex compositions or coating carriers for semi-gloss and matte interior coating compositions. Latex coating compositions have captured a significant portion of the interior and exterior coatings market due to several advantages compared to organic solvent-based types.

[0093] The coating formulations disclosed herein may comprise a film-forming agent, a binder, one or more surfactants selected from one or more surfactant classes, one or more desiccants, one or more pigments, one or more solvents, and water.

[0094] 1. Film-forming agents: Film-forming agents are a group of chemicals that leave a soft, cohesive, and continuous coating on a surface. This film is highly hydrophilic. Film-forming agents comprise a large class of chemicals, which can be broadly classified into two categories: natural and synthetic.

[0095] Natural film-forming agents include oils, rosin, carbohydrates, and egg whites. These natural film-forming agents may include cyclic low-terpenes, polyterpenes, and shellac (such as starch, cellulose, etc.).

[0096] Synthetic film-forming agents include condensation polymers, addition polymers, and polymer resins. These agents may include alkyd resins, polyesters, polyamide / imide resins, silicone resins, crosslinking materials such as phenolic resins, melamine resins, urea resins, polyurethanes, epoxy resins, polyolefins, polyethylene resins, and polyacrylic acid resins.

[0097] Latex coatings typically contain synthetic film-forming agents, such as polyacrylate resins and alkyd resins, as discussed further below.

[0098] a. Latex emulsions are commonly used in the formulation of two types of latex coatings: all-acrylic systems, such as those using copolymers of methyl methacrylate, butyl acrylate, 2-ethylhexyl acrylate, and small proportions of acrylic acid (if desired), and vinyl acetate formulations, which are typically combined with small proportions of lower alkyl acrylates such as 2-ethylhexyl acrylate, methyl methacrylate, or butyl acrylate. To date, all-acrylic systems have been used in high-quality coatings due to their good water resistance, desired leveling properties, film hardness, durability, and scrub resistance. Vinyl acetate-acrylic copolymer systems have been used to formulate interior matte and semi-gloss coatings and exterior wall coatings, and vinyl acetate-butyl acrylate latex results in coating films with excellent toughness, scrub resistance, and durability, while vinyl acetate-dibutyl maleate emulsions offer good abrasion resistance, flexibility, and durability.

[0099] By polymerizing wet-adhesion monomers into copolymers, both acrylic and vinyl acetate systems have been endowed with wet adhesion properties—that is, the quality of adhesion to previously coated, aged surfaces under wet or damp conditions. Typically, these monomers have terminal olefinic unsaturation at one end and terminal urea groups or urea functionality at the other. While these monomers improve the ability of emulsions to adhere to previously coated films under wet conditions, they are sometimes difficult to polymerize into systems, especially acrylic systems, and it is difficult to obtain other desired properties in coatings. Therefore, wet adhesion properties are imparted to coating carriers by blending different types of acrylic polymer emulsions to obtain the overall properties required in the coating carrier, such as durability, wet adhesion, scrub resistance, flexibility, good leveling properties, abrasion resistance, and toughness.

[0100] Suitable emulsions include vinyl acetate latex. For indoor and outdoor applications, vinyl acetate can be copolymerized with monomers to which it can be copolymerized, namely, lower alkyl acrylates, such as C1-C6 esters of acrylic acid and methacrylic acid, including methyl methacrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate; olefins, such as ethylene; alkyl esters of α-β-unsaturated dicarboxylic acids, such as dibutyl maleate, dibutyl fumarate, dioctyl maleate, dibutyl itaconic acid; vinyl chloride, vinyl esters, such as vinyl butyrate, vinyl propionate; vinyl ethers, such as methyl vinyl ether, n-butyl vinyl ether; and unsaturated carboxylic acids and amides, such as acrylic acid and methacrylic acid, acrylamide and methacrylamide.

[0101] For wet adhesion to be achieved in emulsions, which is necessary in most coating applications, wet adhesion monomers can be copolymerized with vinyl acetate to form vinyl acetate terpolymers. They can also be copolymerized with other monomers and blended with vinyl acetate copolymers to obtain wet adhesion. As used herein, “wet adhesion monomer” should be understood to refer to monomers that have allyl or acrylic unsaturation in one part of the molecule and a side-chain urea or acyclic and cyclic urea functional group at the other end.

[0102] Latex may be present in the formulation in an amount of about 40% by weight or more, about 45% by weight or more, about 50% by weight or more, about 55% by weight or more, or about 60% by weight or less, about 65% by weight or less, about 70% by weight or less, or in any range using these endpoints as a percentage of the total formulation.

[0103] Vinyl acetate may be present in the copolymer in amounts of about 25% by weight or more, about 35% by weight or more, about 45% by weight or more, about 55% by weight or more, about 65% by weight or more, about 75% by weight or more, or about 80% by weight or less, about 85% by weight or less, about 90% by weight or less, about 95% by weight or less, about 98% by weight or less, or in any range using these endpoints.

[0104] Comonomers, such as lower alkyl acrylates or olefins, may be present in the copolymer. The comonomers may be present in about 5% by weight or more, about 8% by weight or more, about 10% by weight or more, or about 12% by weight or less, about 15% by weight or less, about 17% by weight or less, about 20% by weight or less, or in any range using these endpoints, as a percentage of the polymer weight.

[0105] Wet adhesion monomers, such as monomers having an allyl or acrylic unsaturation in one part of the molecule and a side-chain urea or acyclic and cyclic urea functional group at the other end, may be included in coating formulations. The wet adhesion monomer may be present in the coating formulation in amounts ranging from about 0.2% by weight or more, about 0.4% by weight or more, about 0.8% by weight or more, about 1.0% by weight or more, about 1.2% by weight or more, or about 1.4% by weight or less, about 1.6% by weight or less, about 1.8% by weight or less, about 2.0% by weight or less, about 2.2% by weight or less, about 2.4% by weight or less, about 2.6% by weight or less, or in any range using these endpoints, as a percentage of the polymer weight.

[0106] Regarding quaternary copolymers, suitable compositions may include vinyl chloride, vinyl acetate, ethylene, and wet-adhesion monomers.

[0107] Vinyl chloride may be present in amounts of about 25% by weight or more, about 30% by weight or more, about 35% by weight or more, about 40% by weight or more, about 45% by weight or more, or about 50% by weight or less, about 55% by weight or less, about 60% by weight or less, about 65% by weight or less, or in any range using these endpoints, as a percentage of the total polymer weight.

[0108] Vinyl acetate may be present in amounts of about 30% by weight or more, about 35% by weight or more, about 40% by weight or more, about 45% by weight or more, or about 50% by weight or less, about 55% by weight or less, about 60% by weight or less, about 65% by weight or less, or in any range using these endpoints, as a percentage of the total polymer weight.

[0109] Ethylene may be present in amounts of about 10% by weight or more, about 11% by weight or more, about 12% by weight or more, or about 13% by weight or less, about 14% by weight or less, about 15% by weight or less, or in any range using these endpoints as a percentage of the total polymer weight.

[0110] The wet-adhesion monomer may be present in amounts of about 0.2% by weight or more, about 0.4% by weight or more, about 0.8% by weight or more, about 1.0% by weight or more, about 1.2% by weight or more, or about 1.4% by weight or less, about 1.6% by weight or less, about 1.8% by weight or less, about 2.0% by weight or less, about 2.2% by weight or less, about 2.4% by weight or less, about 2.6% by weight or less, or in any range using these endpoints.

[0111] b. Alkyd resin coating formulations may contain one or more binders. Suitable binders include various types of alkyd resins. Exemplary alkyd resins include alkyd resins having short, medium, long, and very long oil lengths. The term "alkyd resin" also includes alkyd resins modified with other resins, such as acrylic resins, epoxy resins, phenolic resins, polyurethanes, polystyrene, silicone, rosin and rosin ester alkyd resins, and bio-alkyd resins, such as Setal 900 SM-90, wherein the polyester segments are derived from renewable acids and esters.

[0112] The coating formulation may contain a binder in an amount of about 1% by weight or more, about 5% by weight or more, about 10% by weight or more, about 15% by weight or more, about 25% by weight or more, about 30% by weight or more, or about 35% by weight or less, about 40% by weight or less, about 50% by weight or less, about 60% by weight or less, or in any range using these endpoints, based on the total weight of the composition.

[0113] 2. Surfactants The coating formulations of the present invention comprise one or more surfactants, also referred to as surfactant systems. The surfactant system comprises at least one surfactant, which may be an amphoteric surfactant, an amphoteric surfactant, a cationic surfactant, a nonionic surfactant, and optionally at least one other surfactant, which may be an amphoteric surfactant, an amphoteric surfactant, a cationic surfactant, a nonionic surfactant, or a combination thereof. The surfactant system is present in the coating formulation to help stabilize the emulsion.

[0114] Suitable surfactants for use in coating formulations disclosed herein include one or more surfactants of formula I or II and / or co-surfactants. Formula I Equation II, where R 1 and R 2 They may be the same or different, and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylic acid esters; R 3 Selectable from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to another surfactant molecule having the structure shown in Formula I, wherein the other surfactant molecule of Formula I may be the same as or different from the surfactant molecule of Formula I; n and z may be independently selected from any integer from 1 to 12; m may be any integer from 1 to 12; and X may be selected from chloride ions, bromide ions, and iodide ions.

[0115] Specifically, R 3 Optional from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkages attached to the second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0116] More specifically, R 3 The following formula can be selected: .

[0117] In particular, suitable surfactants or co-surfactants may include any one of the surfactants 1-12 described herein.

[0118] The total amount of one or more surfactants in a coating formulation may be about 0.5% by weight or more, about 1% by weight or more, about 2% by weight or more, or about 3% by weight or less, about 4% by weight or less, about 5% by weight or less, or in any range using these endpoints.

[0119] 3. Desiccant Coating Formulations may contain one or more desiccants. A desiccant is a catalyst used to accelerate the drying process. Suitable desiccants may include oxidation catalysts such as cobalt or manganese salts, polymerization catalysts such as zirconium salts, and / or auxiliary catalysts controlling film formation such as calcium salts. The desiccant enables the coating to dry completely within a few hours, such as three hours, two hours, or less, after application to the surface. Cobalt or manganese esters are oxidation catalysts that play a role in initiating the oxidation process and include C6-C... 19 Esters of branched-chain fatty acids. Examples are cobalt 2-ethylhexanoate, cobalt propionate, cobalt neodecanoate, cobalt naphthenate, a cobalt-intercalated polymer product known as ECOS ND15 available from Umicore, manganese octoate, and a manganese-amine complex known as Nuodex Drycoat available from Huntsman.

[0120] The desiccant composition may be included in the coating formulation in an amount of about 0.1% by weight or more, about 0.3% by weight or more, about 0.6% by weight or more, or about 1.0% by weight or less, about 1.2% by weight or less, about 1.5% by weight or less, about 3.5% by weight or less, about 6.0% by weight or less, or in any range using these endpoints.

[0121] 4. Pigments used in water-based coating compositions typically contain opaque pigments that impart opacity or opacity to the coating film. The coating formulations disclosed herein may contain one or more pigments to color the composition and / or provide opacity. As used herein, pigments include inorganic metal oxides and organic colored pigments. Suitable pigments include metal oxides such as titanium oxide and iron oxide, zinc chromate, chromium oxide, cadmium sulfide, azurite (made from kaolin, sodium carbonate, sulfur, and carbon), and Lithopone (a blend of zinc sulfide and barium sulfate). Examples of organic colored pigments are phthalocyanine blue (α and β), dinitroaniline orange (PO-5), perylene red, toluidine red (PR-3), diarylide yellow (PY-12, 13), and quinacridone red (PV-19).

[0122] Pigments may be included in the coating composition in amounts of about 0% or more, about 1% or more, about 5% or more, about 10% or more, or about 15% or less, about 20% or less, about 25% or less, about 30% or less, or in any range using these endpoints.

[0123] 5. Solvent-based coating formulations may contain one or more aqueous or organic solvents, such as mineral oil and alcohols. Suitable solvents include hydrocarbon solvents or blends thereof. Hydrocarbon solvents may be aliphatic or aromatic solvents. Examples of organic solvents are petroleum distillates such as pentane, hexane, petroleum naphtha, heptane, and 90 solvent (aliphatic solvents with a flash point of 140℉). Aromatic solvents include xylene, toluene, Aromatic 100, and other suitable aromatic solvents. The term "mineral oil," also known as "white oil," includes solvents containing C7-C... 12 A composition of a mixture of aliphatic and alicyclic hydrocarbons, and in a more particular embodiment containing 15%-20% by weight or less of C7-C4 hydrocarbons. 12 Aromatic hydrocarbons, based on the total weight of the composition. Mineral oils include mixtures or blends of alkanes, cycloalkanes, and aromatics. Typical mineral oils have a boiling range of about 150°C to 220°C, are generally clear water-white liquids, are chemically stable and non-corrosive, and have a mild odor. Exemplary mineral oils include low-aromatic white oils (LAWS), such as Shell Sol 15 (CAS 64742-88-7) and Shell Sol H (CAS 64742-82-1). The term "alcohol" is intended to include C1-C... 12 Alcohols, including C1-C 12 Straight-chain and branched-chain alcohols. Exemplary alcohols include triethylene glycol (CAS 112-27-6) and diethylene glycol ethyl ether (CAS 111-90-0). In a more specific embodiment, the coating composition comprises a solvent selected from xylene, mineral oil, alcohols, water, and combinations thereof.

[0124] The amount of solvent in the coating formulation may be about 5% by weight or more, about 10% by weight or more, about 15% by weight or more, about 17% by weight or more, about 20% by weight or more, about 25% by weight or more, or about 30% by weight or less, about 40% by weight or less, about 60% by weight or less, or in any range using these endpoints.

[0125] 6. Other additives: Coating formulations may further include one or more additives, such as fillers, pigments, surfactants, stabilizers, thickeners, emulsifiers, texture additives, adhesion promoters, biocides, flow promoters, dispersants, and additives for changing viscosity or finishing appearance.

[0126] The additive may be included in the coating formulation in amounts of about 0.1% by weight or more, about 0.5% by weight or more, about 1.0% by weight or more, about 1.5% by weight or more, or about 2.0% by weight or less, about 5.0% by weight or less, about 10.0% by weight or less, about 20% by weight or less, about 25% by weight or less, about 30% by weight or less, or in any range using these endpoints.

[0127] Coating formulations may contain one or more fillers to thicken and increase the volume of the composition. Suitable fillers include titanium dioxide, calcium carbonate, clay, and talc.

[0128] Coating formulations may contain one or more additives selected from surfactants, stabilizers, thickeners, emulsifiers, texture additives, adhesion promoters, biocides, and additives used to change viscosity or finish appearance.

[0129] 7. Preparation Method: Coating formulations can be synthesized starting from a standard premix of protective colloids, surfactants, and oxidants. Monomers may be added subsequently, followed by additional surfactants and reducing agents.

[0130] Protective colloids may contain hydroxyethyl cellulose, polyvinyl alcohol, casein, hydroxyethyl starch, and carboxymethyl cellulose.

[0131] The amount of protective colloid added may be about 0.05% or more, about 0.1% or more, about 0.5% or more, about 1.0% or more, about 1.5% or more, about 2% or more, or about 2.5% or less, about 3.0% or less, about 3.5% or less, about 4.0% or less, about 4.5% or less, or within any range using these endpoints.

[0132] The free radical initiating catalyst used to achieve polymerization is generally called a redox catalyst. As is known, redox catalysts include an oxidizing agent and a reducing agent. The oxidizing and reducing components can be any of those commonly used in vinyl acetate emulsion polymerization, such as hydrogen peroxide, potassium persulfate, tert-butyl peroxypentanoate, etc., and preferred reducing agents are ferrous ammonium sulfate and sodium formaldehyde sulfoxylate or zinc formaldehyde sulfoxylate.

[0133] The premix can be formed by adding a standard amount of water, a protective colloid such as hydroxyethyl cellulose, and a free radical initiating oxidant to a first container. Then, approximately 0-70% of the total surfactant used can be added to the first container and mixed therein. The remaining surfactant is mixed with the monomers in a second container or added separately. In either case, they can be added after a delay. To initiate polymerization, the monomers and reducing agent can be added to the first container over a period of time and at a certain rate, such that the unreacted vinyl acetate in the first container remains at approximately 3-5% by weight of the emulsion or latex. After all the monomers have been added to the first container, the residual vinyl acetate is then reduced to less than 0.5% by adding additional oxidant and reducing agent. At the end of polymerization, the pH can be adjusted to approximately 5.5 by adding a base such as ammonium hydroxide.

[0134] Regarding the polymerization process, protective colloids, particularly cellulose ethers, are used to maintain emulsion stability. Higher levels of colloids tend to improve stability and also increase particle size. Surfactants also provide emulsion stability. However, unlike colloids, surfactants tend to reduce particle size when present in the initial polymerization and show better particle size reduction effects when added later. Particle size optimization can be achieved by working protective colloids and surfactants together.

[0135] Stirring is another variable that can affect the particle size in polymer emulsions. Stirring should be gentle to ensure proper heat transfer and maintain product stability. Vigorous stirring should be avoided. Regarding particle size control, if larger particles are desired, the stirring rate can be reduced; and if smaller particles are desired, the intensity of stirring can be increased. If stirring cannot be changed, adjustments can be made to the surfactant or protective colloid.

[0136] III. Adhesive Formulations This disclosure also provides adhesive formulations. The adhesive formulations of this disclosure can be used in the manufacture of wood-based panels, such as plywood, scaleboard, blackboard, fiberboard, OBS board, or equivalents.

[0137] The adhesive formulations disclosed herein may comprise a resin, a filler, a solvent, and one or more surfactants selected from one or more surfactant classes.

[0138] 1. Resin. The resin is present in the adhesive formulation to serve as the adhesive itself. Suitable resins may include phenolic resins, urea-formaldehyde resins, amino resins, or other corresponding resins. In one embodiment, the resin used is UF (urea-formaldehyde resin), MUF (melamine-urea-formaldehyde resin), MUFP (modified urea-formaldehyde polymer), PF (phenolic resin), or derivatives or mixtures of these or equivalents.

[0139] The resin may be present in the adhesive formulation in amounts of about 40% by weight or more, about 45% by weight or more, about 50% by weight or more, about 55% by weight or more, or about 60% by weight or less, about 65% by weight or less, about 70% by weight or less, about 75% by weight or less, about 80% by weight or less, or in any range using these endpoints.

[0140] 2. Filler As used herein, "filler" refers to a filler or hardener known in its own right, or a mixture thereof. Hardeners, in application, i.e., during the manufacture of wood-based panels, are generally preferred to affect the curing of the adhesive in conjunction with heat of compression. Suitable fillers may include starch, wheat flour, chalk, sodium carbonate, potassium carbonate, calcium carbonate, ammonium sulfate, wood flour, kaempferia galanga, or derivatives thereof, or mixtures thereof, or equivalents. Kaempferia galanga refers to the hardwood of certain South American broadleaf trees. As used herein, "chalk" refers to loosely structured, lightweight, and broken limestone.

[0141] The filler may be present in the adhesive composition in amounts of about 5% by weight or more, about 10% by weight or more, about 15% by weight or more, or about 20% by weight or less, about 25% by weight or less, about 30% by weight or less, or in any range using these endpoints.

[0142] 3. Solvent-based adhesive formulations may contain solvents, such as water. The water may be obtained from outside the process, or it may be water recycled from within the process, i.e., process wash water. Alternatively, the solvent may be an organic solvent.

[0143] The solvent may be present in the adhesive composition in amounts of about 0% or more, about 5% or more, about 10% or more, about 15% or more, about 20% or more, or about 25% or less, about 30% or less, about 35% or less, about 40% or less, or in any range using these endpoints.

[0144] 4. Surfactant: One or more surfactants may be included in the adhesive formulation as foaming agents, with the explicit purpose of promoting foaming. Suitable surfactants for use in the adhesive formulations of this disclosure include one or more surfactants of formula I or II and / or co-surfactants. Formula I Equation II, where R 1 and R 2They may be the same or different, and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylic acid esters; R 3 Selectable from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to another surfactant molecule having the structure shown in Formula I, wherein the other surfactant molecule of Formula I may be the same as or different from the surfactant molecule of Formula I; n and z may be independently selected from any integer from 1 to 12; m may be any integer from 1 to 12; and X may be selected from chloride ions, bromide ions, and iodide ions.

[0145] Specifically, R 3 Optional from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkages attached to the second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0146] More specifically, R 3 The following formula can be selected: .

[0147] In particular, suitable surfactants or co-surfactants may include any one of the surfactants 1-12 described herein.

[0148] The adhesive formulation may contain one or more surfactants in amounts of about 0.1% by weight or more, about 0.5% by weight or more, about 1% by weight or more, about 2% by weight or more, about 3% by weight or more, about 4% by weight or more, or about 5% by weight or less, about 6% by weight or less, about 7% by weight or less, about 8% by weight or less, about 9% by weight or less, about 10% by weight or less, or in any range using these endpoints.

[0149] 5. Other additive adhesive formulations may contain one or more additional compatible ingredients. These additional ingredients may include, for example, one or more additional surfactants that are not solely intended for foaming purposes, such as the surfactants disclosed herein. These additional surfactants may be present in the adhesive formulation in amounts of about 0.1% by weight or more, about 0.5% by weight or more, or about 1.0% by weight or less, about 1.5% by weight or less, about 2.0% by weight or less, or in any range using these endpoints.

[0150] The adhesive composition may also contain a catalyst.

[0151] 6. Preparation Method Adhesive formulations can be prepared as emulsions. To prepare an emulsion, the liquid components can be mixed together, and the mixture can be cooked at a relatively high temperature (above 40°C).

[0152] IV. Paint Remover This disclosure also provides formulations of paint removers. These compositions can be used to remove adhesives, sealants, and other organic coatings such as enamel, varnish, or lacquer, or other organic coatings, from various substrates, including metallic substrates such as aluminum and aluminum alloys. Typically, the composition is in contact with the surface for a sufficient time to allow the polymer coating to bubble, after which the bubbled coating can be removed with an abrasive material. Alternatively, the coating can be removed by spraying water onto the bubbled coating to lift it from the surface.

[0153] The paint stripping formulation disclosed herein may comprise dichloroethylene, one or more surfactants selected from one or more surfactant classes, one or more cosolvents, corrosion inhibitors, waxes, thickeners, organic solvents, and water.

[0154] 1. The dichloroethylene stripping agent may contain dichloroethylene (1,1-dichloroethylene, cis-1,2-dichloroethylene, trans-1,2-dichloroethylene or mixtures thereof).

[0155] Dichloroethylene may be present in the stripping formulation in amounts of about 55% by weight or more, about 57% by weight or more, about 59% by weight or more, or about 61% by weight or less, about 63% by weight or less, about 65% by weight or less, or in any range using these endpoints.

[0156] 2. Surfactants. Surfactants may be included in the stripping formulation to increase the solubility of certain components. Suitable surfactants used in the stripping formulations of this disclosure protect one or more surfactants of formula I or II and / or co-surfactants. Formula I Equation II, where R1 and R 2 They may be the same or different, and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylic acid esters; R 3 Selectable from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to another surfactant molecule having the structure shown in Formula I, wherein the other surfactant molecule of Formula I may be the same as or different from the surfactant molecule of Formula I; n and z may be independently selected from any integer from 1 to 12; m may be any integer from 1 to 12; and X may be selected from chloride ions, bromide ions, and iodide ions.

[0157] Specifically, R 3 Optional from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkages attached to the second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0158] More specifically, R 3 The following formula can be selected: .

[0159] In particular, suitable surfactants or co-surfactants may include any one of the surfactants 1-12 described herein.

[0160] The surfactant may be present in the peeling formulation in amounts of about 1% or more, about 2% or more, about 3% or more, about 4% or more, about 5% or more, or about 6% or less, about 7% or less, about 8% or less, about 9% or less, about 10% or less, or in any range using these endpoints.

[0161] 3. Cosolvents Cosolvents can be used to increase the swelling of the target coating. The stripping formulations of this disclosure may contain such cosolvents. Suitable solvents may include aromatic alcohols and aromatic ethers, such as diphenoxybenzene, propoxybenzene, methoxybenzene, ethoxybenzene, benzyl ether, diphenyl ether, cyclopentanol, naphthol, benzyl alcohol, toluene, pentamethylbenzyl alcohol, and other aromatic alcohols containing a hydroxyl group in the aromatic ring side chain. Other suitable solvents may include aliphatic alcohols, ethanol, propionaldehyde, butanol, pentanol, hexanol, and alcohols having up to 12 carbons. Such cosolvents are generally considered environmentally friendly and non-toxic, and can be effective cosolvents without requiring additional activators for stripping formulations containing 1,2-dichloroethylene.

[0162] Aromatic alcohols and aromatic ethers may be present in the peeling formulation in amounts of about 10% by weight or more, about 11% by weight or more, about 12% by weight or more, about 13% by weight or more, about 14% by weight or more, about 15% by weight or more, or about 16% by weight or less, about 17% by weight or less, about 18% by weight or less, about 19% by weight or less, about 20% by weight or less, or in any range of these endpoints.

[0163] Aliphatic alcohols may be present in the peeling formulation in amounts of about 1% or more, about 2% or more, about 3% or more, about 4% or more, about 5% or more, or about 6% or less, about 7% or less, about 8% or less, about 9% or less, about 10% or less, or in any range using these endpoints.

[0164] 4. Corrosion Inhibitor The stripping formulations disclosed herein may contain a corrosion inhibitor. Suitable corrosion inhibitors may include benzimidazole, indole, benzoxazole, and mixtures of these corrosion inhibitors, as well as triazoles such as benzotriazole and methylbenzotriazole.

[0165] Corrosion inhibitors may be included in the peeling formulation in an effective amount of about 0% or more, about 1% or more, about 2% or more, about 3% or more, about 4% or more, about 5% or more, or about 6% or less, about 7% or less, about 8% or less, about 9% or less, about 10% or less, or in any range using these endpoints.

[0166] 5. The exfoliating formulation disclosed herein may contain wax. Suitable waxes include paraffin. To facilitate mixing with other components of the exfoliating formulation, the wax may be dissolved in a solvent prior to mixing with the other components. Solvents that are substantially nonpolar or lipophilic may be used for this purpose. Suitable solvents include aromatic and aliphatic hydrocarbons, such as benzene, toluene, xylene, hexane, cyclohexane, heptane, octane, and similar straight-chain and branched hydrocarbons and mixtures thereof. This includes fractions from petroleum mineral distillations and various mixtures of these solvents.

[0167] Wax may be present in the peeling formulation in amounts of about 1.0% or more, 1.5% or more, 2.0% or more, 2.5% or more, or 3.0% or less, 3.5% or less, 4.0% or less, 4.5% or less, or 5.0% or less, or in any range using these endpoints.

[0168] 6. Thickening Agent The peeling formulations disclosed herein may contain a thickening agent. In applications where a vertical surface will be treated with the formulation, the thickening agent may be used to maintain the formulation on the coating surface for an extended period sufficient to loosen the coating. Suitable thickening agents may contain cellulose, such as ethyl cellulose, ethyl hydroxyethyl cellulose, methyl cellulose, colloidal silica, clays such as bentonite, starch colloidal alumina, or gum arabic.

[0169] Thickeners may be present in the peeling formulation in amounts of 0% or more, 1.0% or more, 1.5% or more, 2.0% or more, 2.5% or more, or 3.0% or less, 3.5% or less, 4.0% or less, 4.5% or less, or 5.0% or less, or in any range using these endpoints.

[0170] 7. Solvents The peeling formulations disclosed herein may contain additional solvents, such as organic solvents and water.

[0171] Organic solvents may be present in the peeling formulation in amounts of about 1.0% by weight or more, 1.5% by weight or more, 2.0% by weight or more, 2.5% by weight or more, or 3.0% by weight or less, 3.5% by weight or less, 4.0% by weight or less, 4.5% by weight or less, or 5.0% by weight or less, or in any range using these endpoints.

[0172] Water may be present in the peeling formulation in amounts of about 1% or more by weight, about 5% or more by weight, about 8% or more by weight, about 10% or more by weight, or about 12% or less by weight, about 15% or less by weight, about 18% or less by weight, about 20% or less by weight, or in any range using these endpoints.

[0173] 8. Method of Use The peeling formulations disclosed herein are generally applied to the surface to be peeled in a conventional manner, i.e., by applying the composition by brush or other applicator and then applying it to the surface to be peeled. Alternatively, the formulation can be sprayed onto the surface using a spray system that utilizes the thixotropic properties of the formulation on a vertical panel.

[0174] VI. Surfactants This disclosure provides surfactants in the form of amino acid siloxane derivatives for use in inks, coatings, adhesives, and paint removers. The amino acids may be naturally occurring or synthetic, or they may be obtained from the ring-opening reaction of lactams such as caprolactam. The compounds of this disclosure have shown surface-active properties and can be used, for example, as surfactants and wetting agents. In particular, surfactants in the form of surfactant molecules of formula I or II for use in ink, coating, or adhesive products are provided. Formula I Equation II, where R 1 and R 2 They may be the same or different, and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylic acid esters; R 3 Selectable from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to another surfactant molecule having the structure shown in Formula I, wherein the other surfactant molecule of Formula I may be the same as or different from the surfactant molecule of Formula I; n and z may be independently selected from any integer from 1 to 12; m may be any integer from 1 to 12; and X may be selected from chloride ions, bromide ions, and iodide ions.

[0175] Specifically, R 3 Optional from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkages attached to the second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0176] More specifically, R3 The following formula can be selected: .

[0177] The above discloses formulations comprising at least one surfactant of formula I or II for use in various inks, coatings, or adhesives. The following disclosures of compounds of formula I and II apply to any disclosed use and to compounds of formula I and II in the formulations described herein.

[0178] Other compounds provided in this disclosure are those of formula I, wherein R 1 and R 2 It is a methyl group.

[0179] Other compounds provided in this disclosure are compounds of formula I, wherein n and / or z is 5.

[0180] The phrase “n can be an integer from 1 to 12” as used in this article means that n can be equal to 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12.

[0181] The phrase “C1-C6 alkyl” as used in this article refers to a straight-chain or branched alkyl group containing 1, 2, 3, 4, 5 and / or 6 carbons.

[0182] The phrase “C1-C6 linker” as used in this article refers to a straight-chain or branched alkyl chain containing 1, 2, 3, 4, 5 and / or 6 carbons.

[0183] The phrase “C2-C” used in this article 10 "Alkenyl" refers to a straight-chain or branched alkenyl group containing 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbons.

[0184] The phrase “C2-C” used in this article 10 "Alkyne" refers to a straight-chain or branched alkynyl group containing 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbons.

[0185] The phrase “C2-C” used in this article 12 "Ester" refers to a straight-chain or branched ester group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12 carbons.

[0186] The phrase “C2-C” used in this article 12 "Alkoxyalkyl ether" refers to a straight-chain or branched alkoxyalkyl ether group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12 carbons.

[0187] The phrase “C1-C” used in this article 10 "Hydroxy" refers to a hydroxyl group attached to a straight-chain or branched alkyl group containing 1, 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbons.

[0188] The phrase “C3-C8 carboxylic acid” as used in this article refers to a carboxylic acid group attached to a straight-chain or branched alkyl group containing 3, 4, 5, 6, 7 and / or 8 carbons.

[0189] The phrase “C1-C” used in this article 10 "Alkylbenzoic acid" refers to a benzoic acid group attached to a straight-chain or branched alkyl group containing 1, 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbons.

[0190] The phrase “n and z can be independently selected from any integer from 1 to 12” as used in this article means that n and z can be independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12.

[0191] The phrase “m can be any integer from 1 to 12” as used in this article means that m can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12.

[0192] The phrase “q can be any integer from 1 to 10” as used in this article means that q can be 1, 2, 3, 4, 5, 6, 7, 8, 9 and / or 10.

[0193] A specific compound disclosed herein, referred to herein as surfactant 1, is N-benzyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0194] The second specific compound disclosed herein, referred to herein as surfactant 2, is N-(2-ethoxy-2-oxoethyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0195] The third specific compound disclosed herein, referred to herein as surfactant 3, is N-allyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium iodide, having the following formula: .

[0196] The fourth specific compound disclosed herein, referred to herein as surfactant 4, is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxo-N-(prop-2-yn-1-yl)hex-1-ammonium bromide, having the following formula: .

[0197] The fifth specific compound disclosed herein, referred to herein as surfactant 5, is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(2-(2-methoxyethoxy)ethyl)-N,N-dimethyl-6-oxohexyl-1-ammonium bromide, having the following formula: .

[0198] The sixth specific compound disclosed herein, referred to herein as surfactant 6, is N-(3-(diethoxyphosphoryl)propyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0199] The seventh specific compound disclosed herein, referred to herein as surfactant 7, is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(3-hydroxypropyl)-N,N-dimethyl-6-oxohex-1-ammonium iodide, having the following formula: .

[0200] The eighth specific compound disclosed herein, referred to herein as surfactant 8, is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(2-hydroxyethyl)-N,N-dimethyl-6-oxohex-1-ammonium iodide, having the following formula: .

[0201] The ninth specific compound disclosed herein, referred to herein as surfactant 9, is N-(5-carboxypentyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0202] The tenth specific compound disclosed herein, referred to herein as surfactant 10, is N 1 N 3 -bis(6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-6-oxohexyl)-N 1 N 1 N 3 N 3 -Tetramethylpropane-1,3-diammonium dibromide, having the following formula: .

[0203] Another specific group of compounds provided in this disclosure, referred herein to as surfactants 11-12, has the general formula: , where q can be an integer from 1 to 10.

[0204] The eleventh specific compound disclosed herein, referred to herein as surfactant 11, is N-(4-(4-carboxyphenyl)butyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0205] The twelfth specific compound disclosed herein, referred to herein as surfactant 12, is N-(4-carboxybenzyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0206] These compounds can be synthesized using a variety of methods. One such method involves reacting an amino acid (e.g., an N-alkylated or N-acylated amino acid) with a siloxane to convert the C-terminus of the amino acid into the desired siloxane derivative. For example, the N-terminus of the amino acid can be further alkylated to generate a quaternary ammonium.

[0207] Amino acids can be naturally occurring or synthetic, or derived from ring-opening reactions of lactams (such as caprolactam). Ring-opening reactions can be acid- or base-catalyzed, and examples of acid-catalyzed reactions are shown in Scheme 1 below.

[0208] Option 1 Amino acids may have as few as one or as many as 12 carbons between the N-terminus and C-terminus, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbons. The alkyl chain may be branched or straight. The alkyl chain may be inserted with nitrogen, oxygen, or sulfur. The alkyl chain may be further substituted with one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carboxyl, and carboxylic acid esters. The N-terminal nitrogen may be acylated or alkylated with one or more alkyl groups. For example, an amino acid may be 6-(dimethylamino)hexanoic acid.

[0209] Siloxanes can be substituted with one or more alkoxy groups, such as methoxy, ethoxy, isopropoxy, tert-butoxy, etc. Siloxanes can be further substituted with one or more alkyl groups (e.g., propyl), wherein the alkyl groups can be further substituted with suitable functional groups to allow the siloxane to couple with amino acids, such as nitrogen. For example, a siloxane can be 3-aminopropyltris(trimethylsiloxy)silane.

[0210] The siloxane derivatives of amino acids can be synthesized according to Scheme 2 below. As shown, 6-aminohexanoic acid can be alkylated at the N-terminus by reflux in formic acid with formaldehyde to obtain 6-(dimethylamino)hexanoic acid. Then, the free carboxylic acid is coupled with 3-aminopropyl(trimethylsiloxy)silane in refluxed toluene to obtain the desired siloxane derivative.

[0211] Option 2 The N-terminal nitrogen can be further derivatized to alter or improve water solubility and surface activity. Scheme 3 below shows the sample synthesis scheme in which the N-terminal nitrogen is alkylated to provide quaternary ammonium.

[0212] Option 3 Suitable alkylating agents may include, for example, benzyl bromide, ethyl bromoacetate, allyl iodide, propargyl bromide, 1-bromo-2-(2-methoxyethoxy)ethane, bromophosphonates, 3-iodopropanol, 3-bromopropanol, 2-iodoethanol, 2-bromoethanol, 6-bromohexanoic acid, 4-(4-bromobutyl)benzoic acid, and 4-(bromomethyl)benzoic acid. The two molecules of Formula I can be linked by treating the N-terminal nitrogen with a bifunctional alkylating agent (e.g., 1,3-dibromopropane).

[0213] The compounds disclosed herein exhibit surface-active properties. These properties can be measured and described by various methods. One way to describe surfactants is through the critical micelle concentration (CMC) of the molecule. The CMC can be defined as the concentration of surfactant at which micelles form, and above this concentration, all additional surfactants are incorporated into the micelles.

[0214] As the surfactant concentration increases, the surface tension decreases. Once the surface is completely covered by surfactant molecules, micelles begin to form. This point represents the CMC (Content Mold Value) and the minimum surface tension. Further addition of surfactant will not further affect the surface tension. Therefore, the CMC can be determined by observing the change in surface tension with surfactant concentration. One such method for measuring this value is the Wilhelmy plate method. The Wilhelmy plate is typically a thin iridium-platinum plate, which is attached to a balance by a wire and placed perpendicular to the air-liquid interface. The balance is used to measure the force applied to the plate by wetting. The surface tension (γ) is then calculated using this value according to Equation 1: Equation 1: γ = F / l cos θ where l is equal to the perimeter of wetting (2w + 2d, where w and d are the thickness and width of the plate, respectively), and cosθ, the contact angle between the liquid and the plate, is assumed to be 0 in the absence of existing literature values.

[0215] Another parameter used to evaluate surfactant performance is dynamic surface tension. Dynamic surface tension is the surface tension value over the lifetime (age) of a specific surface or interface. In the case of liquids with added surfactants, this can differ from the equilibrium value. Immediately after surface formation, the surface tension is equal to that of the pure liquid. As mentioned above, surfactants reduce surface tension; therefore, the surface tension decreases until an equilibrium value is reached. The time required to reach equilibrium depends on the diffusion and adsorption rates of the surfactant.

[0216] One method for measuring dynamic surface tension relies on a bubble pressure tensiometer. This device measures the maximum internal pressure of a bubble forming in a liquid via a capillary. The measured value corresponds to the surface tension at a specific surface lifetime (i.e., the time from the start of bubble formation to the occurrence of the maximum pressure). The dependence of surface tension on surface lifetime can be measured by varying the rate at which bubbles are formed.

[0217] Surfactant compounds can also be evaluated by their wetting ability on a solid matrix, which is measured by the contact angle. When a droplet comes into contact with a solid surface in a third medium such as air, a triple line is formed between the liquid, gas, and solid. The angle between the unit vector of surface tension acting on the triple line and tangent to the droplet and the surface is described as the contact angle. The contact angle (also called the wetting angle) is a measure of how well a solid is wetted by a liquid. In the case of complete wetting, the liquid spreads completely over the solid, and the contact angle is 0°. The wetting properties of a given compound are typically measured at concentrations of 1–10 × CMC; however, this is not a concentration-dependent property. Therefore, wetting properties can be measured at higher or lower concentrations.

[0218] In one method, an optical contact angle goniometer can be used to measure the contact angle. This device uses a digital camera and software to extract the contact angle by analyzing the profile shape of a droplet attached to a surface.

[0219] Potential applications of the surfactant compounds disclosed herein include formulations for use in shampoos, conditioners, detergents, spot-free rinsing solutions, floor and carpet cleaners, graffiti removers, wetting agents for crop protection, adjuvants for crop protection, and wetting agents for aerosol spraying.

[0220] Those skilled in the art will understand that small differences between compounds can lead to significantly different surfactant properties, allowing different compounds to be used with different substrates in different applications. They will also understand that the properties of surfactants may not be predictable from their chemical structure, as further demonstrated below. For example, surfactant 9 and the comparative surfactant differ only in the number of methylene groups in R3, yet they exhibit different surfactant properties. Surprisingly, surfactant 9 exhibits superior activity, as further described below, while the comparative surfactant exhibits inferior surfactant properties.

[0221] The following non-limiting embodiments are provided to demonstrate the different properties of various surfactants. In Table 1 below, the abbreviations of surfactants are related to their corresponding chemical structures.

[0222] Table 1 .

[0223] These compounds are effective as surfactants in any formulation contemplated in this disclosure and can be used as wetting or foaming agents, dispersants, emulsifiers, and detergents.

[0224] The compounds disclosed herein may be used in formulations in amounts 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%, about 30 wt%, about 40 wt%, about 50 wt%, about 80 wt%, or in any range from 0.001 wt% to 80 wt%, or 0.05 wt% to 50 wt%, or 0.1 wt% to 20 wt%, or 0.5 wt% to 10 wt%, or 1 wt% to 8 wt%, or 2 wt% to 8 wt%, or 5 wt% to 8 wt%, or in any range using any two of the above values.

[0225] Table 2 contains comparative surfactants, including their names and structures.

[0226] The critical micelle concentration (CMC) of the surfactants that can be used in the formulations disclosed herein may be less than about 15 mmol, less than about 10 mmol, less than about 5 mmol, less than about 1 mmol, less than about 0.8 mmol, less than about 0.7 mmol, less than about 0.6 mmol, less than about 0.5 mmol, less than about 0.4 mmol, less than about 0.3 mmol, less than about 0.2 mmol, less than about 0.1 mmol, less than about 0.05 mmol, or less than about 0.01 mmol, or may have any CMC falling within the range included in the above endpoints. For example, the CMC of the surfactant may be from about 0.01 to about 15 mmol, from about 0.05 to about 10 mmol, or from about 0.1 to about 5 mmol.

[0227] The minimum surface tension plateau value of the surfactants that can be used in the formulations disclosed herein may be less than about 25 mN / m, less than about 24 mN / m, less than about 23 mN / m, less than about 22 mN / m, less than about 21 mN / m, less than about 20 mN / m, less than about 19 mN / m, less than about 18 mN / m, less than about 17 mN / m, less than about 16 mN / m, or less than about 15 mN / m, or may have any minimum surface tension plateau value falling within the range encompassed by the above endpoints. For example, the minimum surface tension plateau value of the surfactant may be about 15 to about 25 mN / m, about 18 to about 22 mN / m, or about 20 to about 21 mN / m.

[0228] Surfactants with antimicrobial activity: Cells are the basic unit of all living organisms, each with its own set of organelles responsible for performing various cellular functions and storing genetic information for the organism's development and function. The cell's outer boundary, called the cell membrane, acts as a barrier and regulates the transport of substances between the inside and outside of the cell. The cell membrane can be disrupted through a process called lysis, leading to cell death, which is the fundamental basis of all antimicrobial processes. The use of surfactants with inherent bactericidal activity can be very important in coatings, adhesives, inks, and various other applications, especially when this function cannot be introduced in other ways, and for economic reasons.

[0229] Traditionally, cationic surfactants have been used as antimicrobial agents in industries such as the food industry and hospitals. Unlike traditional antimicrobial chemicals that rely on a "lock-and-key" mechanism, cationic surfactants are known to exert their antimicrobial activity by disrupting bacterial membranes through electrostatic and hydrophobic interactions. (Zhou & Wang, Structure-activity relationship of cationic surfactants as antimicrobial agents, Current Opinion in Colloids & Interface Science, 45:28-43 (2020)). As good antimicrobial agents, surfactants need to be able to kill bacteria or other unwanted pathogenic microorganisms effectively without interfering with mammalian cells. Currently, with increasing awareness of the potential cytotoxicity and environmental hazards of certain chemicals, collaborative efforts are underway to develop surfactants that reduce cytotoxicity issues, which may arise from the lack of selectivity of conventional quaternary ammonium surfactants, which are known to indiscriminately disrupt biofilms regardless of cell type.

[0230] The surfactants of this disclosure have been evaluated for antimicrobial activity using a standard protocol known as the minimum inhibitory concentration (MIC) test. The table below shows the MIC results for examples of surfactants in this disclosure.

[0231] Surfactant 6 Interval Results Inoculum: Pseudomonas aeruginosa (9027), sequentially diluted 1:10; 2000 ppm maximum value 24 hours not detected Inoculum: Staphylococcus aureus (6538), sequentially diluted 1.7-fold; 400 ppm maximum value 24 hours 138 + / - 57 ppm Inoculum: Escherichia coli (8739), sequentially diluted 1:10; 2000 ppm maximum value 24 hours not detected Inoculum: Streptococcus mutans (25715), sequentially diluted 1.7-fold; 400 ppm maximum value 24 hours 81 + / - 34 ppm Surfactant 7 Inoculum: Pseudomonas aeruginosa (9027), sequentially diluted 1.7-fold; 400 ppm maximum value 24 hours 81 + / - 34 ppm inoculum: Staphylococcus aureus (6538), sequentially diluted 1:10; 2000 ppm maximum value not detected after 24 hours. Inoculum: Escherichia coli (8739), sequentially diluted 1.7-fold; 400 ppm maximum value not detected after 24 hours. 81 + / - 34 ppm inoculum: Streptococcus mutans (25715), sequentially diluted 1:10; 2000 ppm maximum value not detected after 24 hours. Surfactant 9 inoculum: Pseudomonas aeruginosa (9027), sequentially diluted 1:10; 2000 ppm maximum value not detected after 24 hours. Inoculum: Staphylococcus aureus (6538), sequentially diluted 1.7-fold; 400 ppm maximum value not detected after 24 hours. 138 + / - 57 ppm inoculum: *Escherichia coli* (8739), sequentially diluted 1:10; 2000 ppm maximum value 24 hours not measured. Inoculum: *Streptococcus mutans* (25715), sequentially diluted 1.7-fold; 400 ppm maximum value 24 hours 81 + / - 34 ppm. ADBAC control inoculum: *Pseudomonas aeruginosa* (9027), sequentially diluted 1.7-fold; 400 ppm maximum value 24 hours 48 + / - 20 ppm. Inoculum: *Staphylococcus aureus* (6538), sequentially diluted 1.7-fold; 20 ppm maximum value 24 hours 7 + / - 3 ppm. Inoculum: *Escherichia coli* (8739), sequentially diluted 1.7-fold; 20 ppm maximum value 24 hours 16 + / - 7 ppm. Inoculum: *Streptococcus mutans* (25715), sequentially diluted 1.7-fold; 20 ppm maximum value 24 hours 7 + / - 3 ppm. Table of Examples

[0232] Nuclear magnetic resonance (NMR) spectroscopy was performed using a Bruker 500 MHz spectrometer. Critical micelle concentration (CMC) was determined at 23°C using a Wilhelmy plate method with a tensiometer equipped with Pt-Ir plates (DCAT 11, DataPhysics Instruments GmbH). Dynamic surface tension was measured at 23°C using a bubble pressure tensiometer (Krüss BP100, Krüss GmbH). Contact angle was measured using an optical contact angle goniometer equipped with a digital camera (OCA 15 Pro, DataPhysics GmbH).

[0233] Example 1: Synthesis of 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)hexanoamide. 6-(dimethylamino)hexanoic acid (2.00 g, 12.56 mmol, 1 equivalent) was dissolved in toluene (50 mL) in a 100 mL round-bottom flask equipped with a Dean Stark separator. Then, 3-aminopropyltris(trimethylsiloxy)silane (5.48 mL, 13.81 mmol, 1.1 equivalent) was added. The reaction vessel was heated and the reaction was refluxed for 24 hours until no more water separated in the Dean Stark tube. The solvent was removed under vacuum to give the desired siloxane derivative as a yellow oil in 94% yield. 1 H NMR (500 MHz, DMSO)δ: 0.09 (s, 27H), 0.28-0.31 (m, 2H), 1.12-1.26 (m,2H), 1.27-1.30 (m, 4H), 1.38-1.41 (m, 2H), 1.94 (t,J= 7.3 Hz, 2H), 2.00 (s,6H), 2.06 – 2.03 (m, 2H), 2.89 (dd,J= 12.9, 6.8 Hz, 2H).

[0234] Example 2a: Synthesis of N-benzyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant 1) The siloxane derivative described in Example 1 (1 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL). Benzyl bromide (518 mg, 3.03 mmol) was added, and the mixture was heated to 70°C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with acetone to remove excess benzyl bromide, yielding surfactant 1 as a yellow solid (1.1 g).

[0235] Example 2b: Determination of the physical properties of surfactant 1. The critical micelle concentration (CMC) of surfactant 1 was determined. Based on the change in surface tension with concentration in water, the CMC at pH 8 was determined to be approximately 9.883 mmol. The minimum achievable surface tension plateau value of this surfactant is approximately 20.67 mN / m, indicating that this surfactant possesses excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 1.

[0236] Example 3a: Synthesis of N-(2-ethoxy-2-oxoethyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant 2) The siloxane derivative described in Example 1 (1 g, 2.02 mmol) was dissolved in DMF (15 mL), and ethyl bromoacetate (0.25 mL, 2.4 mmol) was added. The mixture was stirred at 70°C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with hexane to give surfactant 2, a brown liquid (900 mg).

[0237] Example 3b: Determination of the physical properties of surfactant 2. The critical micelle concentration (CMC) of surfactant 2 was determined. The CMC was determined to be approximately 0.2171 mmol based on the change in surface tension with concentration in water. The minimum achievable surface tension plateau value of this surfactant is approximately 20.36 mN / m, indicating that this surfactant possesses excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 2.

[0238] Example 4a: Synthesis of N-allyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium iodide (surfactant 3) The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was added to acetonitrile (10 mL), followed by sodium carbonate (0.26 g) and then allyl iodine (674 mg). The mixture was refluxed at 40°C for 14 hours. Residual sodium carbonate was removed by filtration, and the filtrate was concentrated. The crude product was washed twice with hexane to remove excess allyl iodine, yielding surfactant 3, a brown liquid (850 mg).

[0239] Example 4b: Determination of the physical properties of surfactant 3. The critical micelle concentration (CMC) of surfactant 3 was determined. The CMC was determined to be approximately 1.3599 mmol based on the change in surface tension with concentration in water. The minimum achievable surface tension plateau value of this surfactant is approximately 20.67 mN / m, indicating that this surfactant possesses excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 3.

[0240] Example 5a: Synthesis of 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxo-N-(prop-2-yn-1-yl)hex-1-ammonium bromide (surfactant 4) The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL). Propylbromine (674 mg, 2.4 mmol) was added, and the mixture was stirred at 70°C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with hexane to give surfactant 4, a brown liquid (850 mg).

[0241] Example 5b: Determination of the physical properties of surfactant 4. The critical micelle concentration (CMC) of surfactant 4 was determined. The CMC was determined to be approximately 0.2419 mmol based on the change in surface tension with concentration in water. The minimum achievable surface tension plateau value of this surfactant is approximately 20.54 mN / m, indicating that this surfactant possesses excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 4.

[0242] Example 6a: Synthesis of 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(2-(2-methoxyethoxy)ethyl)-N,N-dimethyl-6-oxohexyl-1-ammonium bromide (surfactant 5) The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL). 1-Bromo-2-(2-methoxyethoxy)ethane (2.4 mmol) was added, and the mixture was stirred at 70°C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with hexane to give surfactant 5, a brown liquid (800 mg).

[0243] Example 6b: Determination of the physical properties of surfactant 5. The critical micelle concentration (CMC) of surfactant 5 was determined. The CMC was determined to be approximately 0.4622 mmol based on the change in surface tension with concentration in water. The minimum achievable surface tension plateau value of this surfactant is approximately 20.40 mN / m, indicating that this surfactant possesses excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 5.

[0244] Example 7a: Synthesis of N-(3-(diethoxyphosphoryl)propyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant 6) The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (20 mL). Bromophosphonate (4.04 mmol) was added, and the mixture was stirred at 70°C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with hexane to give surfactant 6, a brown liquid (900 mg).

[0245] Example 7b: Determination of the physical properties of surfactant 6. The critical micelle concentration (CMC) of surfactant 6 was determined. The CMC was determined to be approximately 0.3989 mmol based on the change in surface tension with concentration in water. The minimum surface tension plateau achievable by this surfactant is approximately 20.48 mN / m, indicating that this surfactant has excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 6.

[0246] Example 8a: Synthesis of 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(3-hydroxypropyl)-N,N-dimethyl-6-oxohex-1-ammonium iodide (surfactant 7) The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in acetonitrile (10 mL). Sodium carbonate (0.26 g) was added, followed by 3-iodopropanol (674 mg). The mixture was stirred at 40°C for 24 hours. Residual alkali was removed by filtration, and the filtrate was concentrated. The crude product was washed twice with hexane to remove excess iodopropanol, yielding surfactant 7 as a brown liquid (780 mg).

[0247] Example 8b: Determination of the physical properties of surfactant 7. The critical micelle concentration (CMC) of surfactant 7 was determined. The CMC was determined to be approximately 0.4568 mmol based on the change in surface tension with concentration in water. The minimum achievable surface tension plateau value of this surfactant is approximately 20.61 mN / m, indicating that this surfactant possesses excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 7.

[0248] Example 9a: Synthesis of 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(2-hydroxyethyl)-N,N-dimethyl-6-oxohex-1-ammonium iodide (surfactant 8) The siloxane derivative (1.00 g, 2.02 mmol) described in Example 1 was dissolved in acetonitrile (10 mL). 2-Iodoethanol (4.04 mmol) was added, and the mixture was stirred at 40°C for 14 hours. The solvent was removed, and the crude product was washed twice with hexane to give surfactant 8 (910 mg).

[0249] Example 9b: Determination of the physical properties of surfactant 8. The critical micelle concentration (CMC) of surfactant 8 was determined. The CMC was determined to be approximately 0.9986 mmol based on the change in surface tension with concentration in water. The minimum achievable surface tension plateau value of this surfactant is approximately 20.41 mN / m, indicating that this surfactant possesses excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 8.

[0250] Example 10a: N 1 N 3 -bis(6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-6-oxohexyl)-N 1 N 1 N 3 N 3 Synthesis of tetramethylpropane-1,3-diammonium dibromide (surfactant 10) The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (20 mL). 1,2-Dibromopropane (1 mmol) was added, and the mixture was stirred at 70°C for 12 hours. The solvent was removed, and the crude product was washed twice with hexane to obtain surfactant 10, a brown liquid (900 mg).

[0251] Example 10b: Determination of the physical properties of surfactant 10. The critical micelle concentration (CMC) of surfactant 10 was determined. The CMC was determined to be approximately 0.0631 mmol based on the change in surface tension with concentration in water. The minimum achievable surface tension plateau value of this surfactant is approximately 22.12 mN / m, indicating that this surfactant possesses excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 10.

[0252] Example 11a: Synthesis of N-(5-carboxypentyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant 9) The siloxane derivative described in Example 1 (1 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL), and 6-bromohexanoic acid (2.02 mmol) was added. The mixture was stirred at 70°C for 12 hours, and then the solvent was removed under vacuum. The crude product was washed twice with hexane to give N-(5-carboxypentyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, a viscous brown liquid (650 mg).

[0253] Example 11b: Determination of the physical properties of surfactant 9. The critical micelle concentration (CMC) of surfactant 9a was determined. The CMC was determined to be approximately 0.2237 mmol based on the change in surface tension with concentration in water. The minimum surface tension plateau achievable by this surfactant is approximately 20.52 mN / m, indicating that this surfactant has excellent interfacial activity. These results are plotted as surface tension versus concentration in Figure 9.

[0254] Comparative Example A1: Synthesis of N-(carboxymethyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (comparative surfactant).

[0255] The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL). Bromoacetic acid (2.02 mmol) was added, and the mixture was stirred at 70°C for 12 hours. The solvent was removed, and the crude product was washed twice with hexane to give surfactant 9b, a brown liquid (700 mg).

[0256] Comparative Example A2: Determination of the physical properties of the comparative surfactant. The critical micelle concentration (CMC) of surfactant 9b was determined. The CMC was determined to be approximately 17.28 mmol based on the change in surface tension with concentration in water. The minimum achievable surface tension plateau value for this surfactant is approximately 29.16 mN / m. These results are plotted as surface tension versus concentration in Figure 11. The results demonstrate the difficulty of predicting surfactant activity based on chemical structure; surfactant 9b, differing only in the number of methylene groups in its carboxylic acid, exhibits excellent activity.

[0257] Example 12: Synthesis of N-(4-(4-carboxyphenyl)butyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant 11) Adding 4-(4-bromobutyl)benzoic acid to the siloxane derivative described in Example 1 yields N-(4-(4-carboxyphenyl)butyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide.

[0258] Example 13: Synthesis of N-(4-carboxybenzyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant 12) Adding 4-(bromomethyl)benzoic acid to the siloxane derivative described in Example 1 yields N-(4-carboxybenzyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide.

[0259] Example 14: Formulation of Ink Fixer In this example, a formulation of an ink fixer is provided. The formulation components are shown in Table 3 below.

[0260] Table 3 Component Function (Weight %) Surfactants 1-12 Any of them Reduce surface tension 0-1.5 Wetting agents 1-20 Metal carboxylates Fixing agents 3-16 Acids pH adjusters As needed Water 36-96 Table Example 15: Formulation of the Coating In this example, a formulation for use as a coating is provided. The formulation is shown in Table 4 below.

[0261] Table 4. Component Functions (Weight %): Polymer Latex 40-70; Surfactant 1-12 (any one); Emulsifier 0.5-5; Pigment (as needed); Water Solvent 25-59.5 Table Example 16: Adhesive Formulation In this example, a formulation for use as an adhesive is provided. The formulation is shown in Table 5 below.

[0262] Table 5 Components, Functional Weight % Phenolic Resin Binder 40-80 Calcium Carbonate, Starch, Wheat Flour Filler 5-30 Surfactant 1-12 of Any Foaming Agent 0.1-10 Water 0-40 Table Example 17: Formulation of Paint Remover In this example, a formulation for use as an insecticide is provided. The formulation is shown in Table 6 below.

[0263] Table 6 Component Functions (Weight %) 1,2-Dichloroethylene Paint Remover 55-65 Benzyl Alcohol Aromatic Co-solvent 10-20 Ethanol Aliphatic Co-solvent 1-10 Naphtha Organic Solvent 1-10 Paraffin Wax 1-5 Thickener Viscosity Regulator 0-5 Surfactant 1-12 Any of the following Solubility Regulators 1-10 Corrosion Inhibitor 0-10 Water 1-20 Table 18. Antimicrobial MIC Studies: Known methods and standard protocols were used, along with various types of microorganisms as treatment targets, to test the antimicrobial properties of surfactants. More specifically, a serial dilution method was employed, using a minimum inhibitory concentration (MIC) test protocol, to measure concentration-dependent microbial growth inhibition against Gram-positive bacteria (e.g., anaerobic Streptococcus mutans and Staphylococcus aureus, which is typically aerobic but can also grow under anaerobic conditions) and Gram-negative bacteria (e.g., anaerobic Escherichia coli or aerobic Pseudomonas aeruginosa).

[0264] The bacteria were multiplied overnight in a suitable culture medium (tryptone soy broth). Prior to testing, the concentration of the test organisms was determined using a spectrophotometer capable of measuring optical density. The bacterial samples were then diluted to approximately 1E3 to 1E4 CFU / mL. Subsequently, 10 mL of the prepared bacterial culture was inoculated into the wells of a 96-well plate, each well containing a suitable culture medium, namely tryptone soy agar. Once inoculated, these wells were treated with serially diluted test samples and incubated at 37±1°C and a relative humidity of at least 90% for approximately 24±1 hours.

[0265] The test surfactant was prepared into a series of dilutions. All dilutions were sequentially applied to 96-well microplates using a multichannel pipette. The dilution series was established previously through a range-finding exercise to determine the upper limit of the high concentration and the lower concentrations of the series of dilutions to ensure that the test substance did not completely inhibit bacterial growth but still showed an effect.

[0266] Then, the MIC is used to determine the approximate concentration of the test surfactant that inhibits bacterial growth.

[0267] In this antimicrobial test protocol, a reference substance is usually used as a positive control. In this example, quaternary ammonium ADBAC with CAS number 139-08-2 is used as a suitable test reference.

[0268] Test measurements were performed on repeated 96-well plates, and the rounded integer mean of the determined MIC was reported. The repeated data were averaged using the formula: Arithmetic Mean = Sum of numbers in the set of interest / Number of items, to determine the mean (arithmetic mean) for the selected measurements. Measurement variability was then reported in the form of MIC + / - based on the determined mean.

[0269] Aspect 1 is a formulation for use in ink fixing solutions, comprising: at least one surfactant of formula I: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; the fixing agent and water.

[0270] Aspect 2 is a formulation of aspect 1, wherein the fixing agent is a metal carboxylate.

[0271] Aspect 3 is a formulation of aspect 1 or aspect 2, and also contains a wetting agent.

[0272] Aspect 4 is a formulation of any one of aspects 1-3, and also contains an acid.

[0273] Aspect 5 is a formulation of any one of aspects 1-4, and also includes an aqueous carrier.

[0274] Aspect 6 is a formulation of any one of aspects 1-5, and further comprises a colorant dispersed in an aqueous carrier.

[0275] Aspect 7 is a formulation for use in coatings, comprising: at least one surfactant of formula I: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; latex; and water.

[0276] Aspect 8 is a formulation of aspect 7, and also contains one or more desiccants.

[0277] Aspect 9 is a formulation of aspect 7 or aspect 8, and also contains one or more solvents.

[0278] Aspect 10 is a formulation of any one of aspects 7-9, and also contains one or more pigments.

[0279] Aspect 11 is a formulation for use in coatings, comprising: at least one surfactant of formula I: Equation I, where R1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; binder; and water.

[0280] Aspect 12 is a formulation of aspect 11, and also contains one or more desiccants.

[0281] Aspect 13 is a formulation of aspect 11 or aspect 12, and also contains one or more solvents.

[0282] Aspect 14 is an formulation of any one of aspects 11-13, and also contains one or more pigments.

[0283] Aspect 15 is a formulation for use in adhesives, comprising: at least one surfactant of formula I: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; adhesive; and water.

[0284] Aspect 16 is a formulation of aspect 15, and also contains fillers.

[0285] Aspect 17 is a formulation for use as a paint remover, comprising: at least one surfactant of formula I: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; 1,2-dichloroethylene; and water.

[0286] Aspect 18 is a formulation of aspect 17, and also contains wax.

[0287] Aspect 19 is a formulation of aspect 17 or aspect 18, and also contains corrosion inhibitors.

[0288] Aspect 20 is a formulation of any one of aspects 17-19, and also contains an organic solvent.

[0289] Aspect 21 is a formulation of any one of aspects 17-20, and also contains a thickener.

[0290] Aspect 22 is a formulation for use as a paint remover, comprising: at least one surfactant of formula I: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12The linker is attached to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; 1,2-dichloroethylene; one or more cosolvents; and water.

[0291] Aspect 23 is a formulation of aspect 22, wherein the one or more cosolvents are selected from aromatic alcohols, aromatic ethers and aliphatic alcohols.

[0292] Aspect 24 is a formulation of aspect 22 or aspect 23, and also contains wax.

[0293] Aspect 25 is a formulation of any one of aspects 22-24, and also contains a corrosion inhibitor.

[0294] Aspect 26 is a formulation of any one of aspects 22-25, and also contains an organic solvent.

[0295] Aspect 27 is a formulation of any one of aspects 22-26, and also contains a thickener.

[0296] Aspect 28 describes the use of compounds of formula I as surfactants in ink fixing formulations: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; wherein the formulation comprises at least one surfactant, fixer, and water of Formula I.

[0297] Aspect 29 is the application of aspect 1, wherein the fixing agent is a metal carboxylate.

[0298] Section 30 is the same as Section 28 or Section 29, and also contains a wetting agent.

[0299] Section 31 is the use of any of sections 28-30, and also contains acids.

[0300] Aspect 32 is the use of any of aspects 28-31, and also includes an aqueous carrier.

[0301] Aspect 33 is the use of any of aspects 28-32, and also includes a colorant dispersed in an aqueous carrier.

[0302] Aspect 34 describes the use of compounds of formula I as surfactants in coating formulations: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; wherein the formulation comprises at least one surfactant of Formula I, latex, and water.

[0303] Aspect 35 is the application of aspect 34 and also contains one or more desiccants.

[0304] Aspect 36 is the use of aspect 34 or aspect 35, and also contains one or more solvents.

[0305] Aspect 37 is the use of any of aspects 34-36, and also includes one or more pigments.

[0306] Aspect 38 describes the use of compounds of formula I as surfactants in coating formulations: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; wherein the formulation comprises at least one surfactant, binder, and water of Formula I.

[0307] Aspect 39 is a formulation of aspect 38 and also contains one or more desiccants.

[0308] Aspect 40 is a formulation of aspect 38 or aspect 39, and also contains one or more solvents.

[0309] Aspect 41 is an formulation of any one of aspects 38-40, and also contains one or more pigments.

[0310] Aspect 42 describes the use of compounds of formula I as surfactants in adhesive formulations: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to a second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; wherein the formulation comprises at least one surfactant, binder, and water of Formula I.

[0311] Aspect 43 is the application of aspect 42, and also includes fillers.

[0312] Aspect 44 describes the use of compounds of formula I as surfactants in paint remover formulations: Equation I, where R 1 and R 2The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; wherein the formulation comprises at least one surfactant of Formula I, 1,2-dichloroethylene, and water.

[0313] Aspect 45 is the application of aspect 44, and also includes wax.

[0314] Section 46 is the same as Section 44 or Section 45, and also includes corrosion inhibitors.

[0315] Aspect 47 is the use of any of aspects 44-46, and also includes organic solvents.

[0316] Aspect 48 is the use of any of aspects 44-47, and also includes a thickener.

[0317] Aspect 49 describes the use of compounds of formula I as surfactants in paint remover formulations: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is attached to a second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; wherein the formulation further comprises 1,2-dichloroethylene; one or more cosolvents; and water.

[0318] Aspect 50 is the use of aspect 49, wherein the one or more co-solvents are selected from aromatic alcohols, aromatic ethers and aliphatic alcohols.

[0319] Aspect 51 is the same as aspect 49 or aspect 50, and also contains wax.

[0320] Aspect 52 is the use of any of aspects 49-51, and also includes corrosion inhibitors.

[0321] Section 53 is the use of any of sections 49-52, and also includes organic solvents.

[0322] Aspect 54 is the use of any of aspects 48-53, and also includes a thickener.

[0323] Aspect 55 is an ink, coating, adhesive or paint remover formulation disclosed in any of aspects 1-27.

[0324] Aspect 56 is the use of the compound of formula (I) as an ink, coating, adhesive or paint remover formulation containing at least one surfactant. Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C 12 Connecting base, the C1-C 12 The linker is connected to the second molecule of Formula I, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions and iodide ions.

[0325] Aspect 57 is a method for preparing an formulation of any one of Aspects 1-6, comprising: synthesizing a compound of formula I. Equation I, where R 1 and R 2The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and a C1-C6 linker connected to a second molecule of Formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; the method comprises: a ring-opening step to open a lactam ring to provide an amino acid having an N-terminus and a C-terminus; a first alkylation step to alkylate the N-terminus to obtain a tertiary amine; a coupling step to react the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to obtain a siloxane derivative; a second alkylation step to alkylate the N-terminus to obtain a quaternary ammonium of Formula I, with the addition of a fixing agent; and water.

[0326] Section 58 is a method for preparing an formulation of any one of Sections 7-14, comprising: synthesizing a compound of formula I. Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 The method comprises: an alkylbenzoic acid and a C1-C6 linker connected to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; the method comprising: a ring-opening step to open a lactam ring to provide an amino acid having an N-terminus and a C-terminus; a first alkylation step to alkylate the N-terminus to obtain a tertiary amine; a coupling step to react the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to obtain a siloxane derivative; a second alkylation step to alkylate the N-terminus to obtain a quaternary ammonium of formula I, and the addition of a latex or binder; and water.

[0327] Section 59 is a method for preparing an formulation of any one of Sections 15-16, comprising: synthesizing a compound of formula I. Equation I, where R1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 The method comprises: an alkylbenzoic acid and a C1-C6 linker connected to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; the method comprising: a ring-opening step to open a lactam ring to provide an amino acid having an N-terminus and a C-terminus; a first alkylation step to alkylate the N-terminus to obtain a tertiary amine; a coupling step to react the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to obtain a siloxane derivative; a second alkylation step to alkylate the N-terminus to obtain a quaternary ammonium of formula I, the addition of a binder; and water.

[0328] Aspect 60 is a method for preparing an formulation of any one of Aspects 17-27, comprising: synthesizing a compound of formula I. Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 An alkylbenzoic acid and a C1-C6 linker connected to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; the method comprises: a ring-opening step to open a lactam ring to provide an amino acid having an N-terminus and a C-terminus; a first alkylation step to alkylate the N-terminus to obtain a tertiary amine; a coupling step to react the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to obtain a siloxane derivative; a second alkylation step to alkylate the N-terminus to obtain a quaternary ammonium of formula I, with the addition of 1,2-dichloroethylene; optionally, the addition of one or more cosolvents; and water.

[0329] Aspect 61 is a method of any one of aspects 57-60, wherein the lactam is caprolactam.

[0330] Aspect 62 is a method of any one of aspects 57-61, wherein in the first alkylation step, the tertiary amine is 6-(dimethylamino)hexanoic acid.

[0331] Aspect 63 is a method of any one of aspects 57-62, wherein in the second alkylation step, the N-terminus is alkylated with an alkylating agent selected from: benzyl bromide, ethyl bromoacetate, allyl iodide, propargyl bromide, 1-bromo-2-(2-methoxyethoxy)ethane, bromophosphonate, 3-iodopropanol, 3-bromopropanol, 2-iodoethanol, 2-bromoethanol, 6-bromohexanoic acid, and 1,3-dibromopropane.

Claims

1. A formulation for use in ink fixing solutions, comprising: at least one surfactant of formula I: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C6 linking groups, said C1-C6 linking groups being linked to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; a fixing agent; and water.

2. The formulation of claim 1, wherein the fixing agent comprises a metal carboxylate.

3. The formulation of claim 1 or claim 2 further comprises a wetting agent, an acid, an aqueous carrier, or a colorant dispersed in an aqueous carrier.

4. A formulation for use in coatings, comprising: at least one surfactant of formula I: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C6 linkers connected to a second molecule of formula I, wherein the second molecule may be the same or different; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; latex or adhesive; and water.

5. The formulation of claim 4 further comprises one or more desiccants, one or more solvents, or one or more pigments.

6. A formulation for use in adhesives, comprising: at least one surfactant of formula I: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C6 linking groups, said C1-C6 linking groups being connected to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; adhesive; and water.

7. The formulation of claim 6 further comprises a filler.

8. A formulation for use as a paint remover, comprising: at least one surfactant of formula I: Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and a C1-C6 linker connected to a second molecule of Formula I, wherein the second molecule may be the same or different; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; 1,2-dichloroethylene; optionally one or more co-solvents selected from aromatic alcohols, aromatic ethers, and aliphatic alcohols; and water.

9. The formulation of claim 8 further comprises a wax, a corrosion inhibitor, an organic solvent, or a thickener.

10. A method for preparing the formulation of any one of claims 1-9, comprising: Synthetic compound I Equation I, where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally, the C1-C6 alkyl group may include one or more oxygen, nitrogen or sulfur atoms or groups containing at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylic acid esters; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 The method comprises: an alkylbenzoic acid and a C1-C6 linker connected to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from chloride ions, bromide ions, and iodide ions; the method comprising: a ring-opening step to open a lactam ring to provide an amino acid having an N-terminus and a C-terminus; a first alkylation step to alkylate the N-terminus to obtain a tertiary amine; a coupling step to react the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to obtain a siloxane derivative; and a second alkylation step to alkylate the N-terminus to obtain a quaternary ammonium of formula I, and the addition of at least one of a fixer, latex, adhesive, binder, 1,2-dichloroethylene or one or more cosolvents, and water.

11. The method of claim 10, wherein the lactam is caprolactam.

12. Use of the formulation of any one of claims 1 to 3 as an ink fixer.

13. Use of the formulation of any one of claims 4 to 5 as a coating.

14. Use of the formulation of any one of claims 6 to 7 as an adhesive.

15. Use of the formulation of any one of claims 8 to 9 as a paint remover.

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