Surfactants for inks, paints, and adhesives

Abstract

Inks, paints, adhesives, and paint strippers may be formulated to contain one or more surfactants from one or more classes of surfactants, such as siloxane derivatives of amino acids having surface-active properties.

Description

[Technical Field]

[0001] Cross-reference of related applications This application claims priority to U.S. Patent Application No. 18 / 795,167, filed on August 5, 2024, which in turn claims priority to U.S. Provisional Patent Application No. 63 / 531,200, filed on August 7, 2023, the disclosures of which are incorporated by reference in their entirety.

[0002] field This disclosure relates to surfactants for use in inks, paints, and adhesives. Such surfactants may include siloxane derivatives of amino acids having surface-active properties. [Background technology]

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

[0004] Surfactants can be nonionic, zwitterionic, cationic, or anionic. In principle, any class of surfactant (e.g., cationic, anionic, nonionic, amphoteric) is suitable, but formulations may contain a combination of two or more surfactants from two or more surfactant classes.

[0005] In most cases, surfactants are amphiphilic molecules that have a relatively water-insoluble hydrophobic "tail" group and a relatively water-soluble hydrophilic "head" group. These compounds can be adsorbed at interfaces such as between two liquids, between gas and liquid, or between solid and liquid. In systems containing relatively polar and relatively nonpolar components, the hydrophobic tail selectively interacts with the relatively nonpolar component, while the hydrophilic head selectively interacts with the relatively polar component. At the interface between water and oil, the hydrophilic head selectively extends into the water, while the hydrophobic tail selectively extends into the oil. When added to a gas-water interface, the hydrophilic head selectively extends into the water, while the hydrophobic tail selectively extends into the gas. In the presence of a surfactant, at least some of the intermolecular interactions between water molecules are disrupted, and at least some of the interactions between water molecules are replaced by generally weaker interactions between at least some of the water molecules and the surfactant. This can result in a decrease in surface tension, which can also help stabilize the interface.

[0006] At sufficiently high concentrations, surfactants may form aggregates that act to limit the exposure of their hydrophobic tails to polar solvents. One such aggregate is a micelle. In a typical micelle, molecules are arranged spherically, with the hydrophobic tail of the surfactant selectively located inside the sphere and the hydrophilic head of the surfactant selectively located outside the micelle, allowing the head to selectively interact with the more polar solvent. The effect of any compound on surface tension and the concentration at which it forms micelles can be useful as defining characteristics of a surfactant. [Overview of the project]

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

[0008] This disclosure provides surfactants for paints, inks, adhesives, and paint strippers, in the form of siloxane derivatives of amino acids having surface-active properties. The amino acids may be natural or synthetic amino acids, or may be obtained through ring-opening reactions of molecules such as lactams, exemplified by caprolactam. The amino acids may be functionalized with different types of siloxane groups to form compounds having surface-active properties. Characteristically, these compounds may have the ability to reduce the critical micelle concentration (CMC) and / or the surface tension of a liquid.

[0009] This disclosure provides a formulation for an ink fixing solution, comprising one or more surfactant molecules having the structure of formula I or II,

[0010] [ka]

[0011] In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, and optionally the C1-C6 alkyl group may comprise one or more atoms from oxygen, nitrogen, or sulfur, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid and C1-C bonded to further surfactant molecules having the structure represented by formula I 12 Further surfactant molecules of formula I may be selected from the group consisting of linkers, and these may be identical or different from the surfactant molecules 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 a surfactant molecule selected from the group consisting of chloride, bromide, and iodide, Optionally, one or more moisture absorbents, a metal carboxylate as a fixing agent, and an acid, are included.

[0012] The formulation may also include one or more colorants dispersed in an aqueous vehicle and an ink vehicle. For the sake of clarity, as disclosed herein and for any formulation provided herein, the molecule of formula II may represent a structure of the following configuration: Formula I - Linker - Formula I In the structure, the molecule of one formula I may be the same as or different from the molecule of the other formula I. In this exemplary configuration, the linker is R in formula I 3 , C1 - C 12 linker.

[0013] The additional surfactant molecule provided by the present disclosure is a compound of formula I or II in which R 1 and R 2 are methyl. Another surfactant molecule provided by the present disclosure is a compound of formula I or II in which n and / or z is 5.

[0014] Specifically, R 3 may be selected from the group consisting of C2 - C 10 alkenyl, C2 - C​​​​​​​​​​ More specifically, R 3 The following set of formulas may be selected.

[0016] [ka]

[0017] Furthermore, the use of compounds of formula I or II described herein as surfactants in ink fixing agent formulations described herein is disclosed. This disclosure further provides a formulation for paints, which comprises one or more surfactant molecules having the structure of formula I or II,

[0018] [ka]

[0019] In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, and optionally the C1-C6 alkyl group may comprise one or more atoms from oxygen, nitrogen, or sulfur, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid and C1-C bonded to further surfactant molecules having the structure represented by formula I 12 Further surfactant molecules of formula I may be selected from the group consisting of linkers, and these may be identical or different from the surfactant molecules of formula I; n and z may be independently selected from any integer between 1 and 12; m may be any integer from 1 to 12; and X may be a surfactant molecule selected from the group consisting of chlorides, bromides, and iodides. As desired, latex, binder, one or more dryers, one or more pigments, one or more solvents, and water. Includes.

[0020] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, where the second molecule of formula I is the same as the first molecule of formula I.

[0021] More specifically, R 3 The following set of formulas may be selected.

[0022] [ka]

[0023] Furthermore, the use of compounds of formula I or II described herein as surfactants in paint formulations described herein is disclosed. This disclosure also provides a formulation for adhesives, which comprises one or more surfactant molecules having the structure of formula I or II,

[0024] [ka]

[0025] In the formula, R 1 and R 2The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, and optionally the C1-C6 alkyl group may comprise one or more atoms from oxygen, nitrogen, or sulfur, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid and C1-C bonded to further surfactant molecules having the structure represented by formula I 12 Further surfactant molecules of formula I may be selected from the group consisting of linkers, and these may be identical or different from the surfactant molecules of formula I; n and z may be independently selected from any integer between 1 and 12; m may be any integer from 1 to 12; and X may be a surfactant molecule selected from the group consisting of chlorides, bromides, and iodides. If desired, a resin, one or more fillers, and a solvent. Includes.

[0026] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, where the second molecule of formula I is the same as the first molecule of formula I.

[0027] More specifically, R3 The following set of formulas may be selected.

[0028] [ka]

[0029] Furthermore, the use of compounds of formula I or II described herein as surfactants in adhesive formulations described herein is disclosed. This disclosure further provides a formulation for paint strippers, which comprises one or more surfactant molecules having the structure of formula I or II,

[0030] [ka]

[0031] In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, and optionally the C1-C6 alkyl group may comprise one or more atoms from oxygen, nitrogen, or sulfur, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid and C1-C bonded to further surfactant molecules having the structure represented by formula I 12 Further surfactant molecules of formula I may be selected from the group consisting of linkers, and these may be identical or different from the surfactant molecules of formula I; n and z may be independently selected from any integer between 1 and 12; m may be any integer from 1 to 12; and X may be a surfactant molecule selected from the group consisting of chlorides, bromides, and iodides. Optionally, dichloroethylene; one or more cosolvents; corrosion inhibitors; waxes; thickeners, and water. Includes.

[0032] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, where the second molecule of formula I is the same as the first molecule of formula I.

[0033] More specifically, R 3 The following set of formulas may be selected.

[0034] [ka]

[0035] Furthermore, the use of compounds of formula I or II described herein as surfactants in paint stripper formulations described herein is disclosed. The above-mentioned and other features of this disclosure, as well as the methods for achieving them, will become more apparent and better understood by referring to the following description of embodiments in conjunction with the accompanying drawings. [Brief explanation of the drawing]

[0036] [Figure 1] Figure 1 shows a plot of surface tension versus concentration of surfactant 1 described in Example 2b. [Figure 2]Figure 2 shows a plot of surface tension versus concentration of surfactant 2 described in Example 3b. [Figure 3] Figure 3 shows a plot of surface tension versus concentration of surfactant 3 described in Example 4b. [Figure 4] Figure 4 shows a plot of surface tension versus concentration of surfactant 4 described in Example 5b. [Figure 5] Figure 5 shows a plot of surface tension versus concentration of surfactant 5 described in Example 6b. [Figure 6] Figure 6 shows a plot of surface tension versus concentration of surfactant 6 described in Example 7b. [Figure 7] Figure 7 shows a plot of surface tension versus concentration of surfactant 7 described in Example 8b. [Figure 8] Figure 8 shows a plot of surface tension versus concentration of surfactant 8 described in Example 9b. [Figure 9] Figure 9 shows a plot of surface tension versus concentration of surfactant 9 described in Example 11b. [Figure 10] Figure 10 shows a plot of surface tension versus concentration of the surfactant 10 described in Example 10b. [Figure 11] Figure 11 shows a plot of surface tension versus concentration of the surfactant described in Comparative Example A2. [Modes for carrying out the invention]

[0037] As used herein, the phrase “within any range using these endpoints” means literally that any range may be selected from any two of the values ​​listed before the phrase, regardless of whether the value is at the lower end of the enumeration or at the higher end of the enumeration. For example, a pair of values ​​may be selected from the two lower values, the two higher values, or the lower value and the higher value.

[0038] As used herein, the term "alkyl" means any saturated carbon chain, whether linear or branched, which may be substituted at any point on the carbon chain. The carbon chain may have 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbons.

[0039] As used herein, the phrase “surface-active” means that the compound in question can reduce the surface tension and / or interfacial tension with other phases of a medium in which it is at least partially dissolved, and therefore can be at least partially adsorbed to a gas-liquid interface and / or other interfaces. The term “surfactant” may be applied to such compounds.

[0040] With regard to the terminology of inaccuracy, the terms “about” and “approximately” may be used interchangeably and mean any measurement that includes the stated measurement and any measurement that is reasonably close to the stated measurement. A measurement that is reasonably close to the stated measurement deviates from the stated measurement by a reasonably small amount that is understood and readily verifiable by a person skilled in the art in the relevant field. Such deviations may be attributed, for example, to measurement errors or small adjustments made to optimize performance. If a person skilled in the art in the relevant field determines that the value relating to such a reasonably small difference is not readily verifiable, the terms “about” and “approximately” may be understood to mean plus or minus 15% of the stated value, for example, plus or minus 15%, plus or minus 12%, plus or minus 10%, plus or minus 9%, plus or minus 8%, plus or minus 8%, plus or minus 7%, plus or minus 6%, plus or minus 5%, plus or minus 4%, plus or minus 3%, plus or minus 2%, or even plus or minus 1%.

[0041] This disclosure provides formulations of inks, paints, adhesives, and paint removers. I. Ink There are several reasons why inkjet printing has become a popular method for recording images on various media surfaces, especially paper. Some of these reasons include the quiet operation of the printers, the ability to record at high speeds, and the ability to record high-quality color images. In addition, these advantages are available to consumers at a relatively low cost. However, while inkjet printing has improved significantly, this improvement has accompanied increased consumer demand for features such as higher speed, higher resolution, full-color image formation, improved stability, and more permanent images.

[0042] Color inkjet printing systems use sets of inkjet inks. These ink sets often contain a group of inks of several different colors, typically four, six, or eight colors (e.g., one or more shades of cyan, magenta, yellow, and / or black), and may also include an image fixer / fixing solution. The fixer is often applied before or after the ink is established on the surface of the printing medium. The fixer is a substantially colorless liquid that interacts with the colorants and / or polymer components of the ink, causing the ink to settle or otherwise fix on the surface of the printing medium.

[0043] The settled colorants deposit on the surface of the medium, resulting in improved image quality attributes such as optical density and saturation. Durability attributes such as water resistance and highlighter smear also benefit from such reactive ink chemistry. Although several suitable ink sets containing fixers are currently available, improvements to existing ink sets are desirable to formulate more durable and reliable inks that produce higher quality printed images on the surface of the printing medium without damaging the ink-containing printer head. While not bound by any theory, it is thought that when the fixer composition is overprinted with the inkjet ink composition on the substrate, in other words, when the ink and fixer come into contact on the surface of the medium, a very effective crashing of the ink colorants occurs, and almost all of the colorants are deposited on the surface of the medium rather than penetrating into the medium and depositing below the surface. At the same time, when the fixer vehicle is mixed with the ink vehicle, it becomes highly wet, and the mixed vehicle quickly penetrates the medium, leaving the colorants behind.

[0044] Such inkjet printing methods, when combined with a fixer and an inkjet ink composition, result in a system and method that provides high-quality, durable inkjet image prints. Using the fixer of this disclosure results in improved image quality attributes, such as optical density, saturation, 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 configuration. In fact, the fixer has been found not to damage the printer head containing it and to exhibit low corrosiveness to the inkjet system and inkjet pen.

[0045] The ink formulations of this disclosure include an inkjet fixer composition comprising one or more surfactants selected from one or more surfactant classes, one or more hygroscopic agents, a metal carboxylate salt as a fixer, and an acid considering adjusting the pH of the composition to about 5.0 to about 7.0. The formulation may also be an aqueous vehicle and one or more colorants dispersed in the ink vehicle.

[0046] 1. Surfactants The ink formulations of this disclosure include one or more surfactants, also referred to as surfactant systems. Surfactants have excellent ability to maintain surface tension and interfacial tension at appropriate levels. Surfactants can also be used as wetting agents and dispersants. Surfactants suitable for use in the ink formulations of this disclosure include one or more surfactants of formula I or II and / or co-surfactants.

[0047] [ka]

[0048] In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, and optionally the C1-C6 alkyl group may comprise one or more atoms from oxygen, nitrogen, or sulfur, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid and C1-C bonded to further surfactant molecules having the structure represented by formula I 12Further surfactant molecules of formula I may be selected from the group consisting of linkers, and these may be identical or different from the surfactant molecules of formula I; n and z may be independently selected from any integer between 1 and 12; m may be any integer from 1 to 12; and X may be selected from the group consisting of chlorides, bromides, and iodides.

[0049] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, where the second molecule of formula I is the same as the first molecule of formula I.

[0050] More specifically, R 3 The following set of formulas may be selected.

[0051] [ka]

[0052] In particular, a suitable surfactant or co-surfactant may include one or more of the surfactants 1 to 12 described herein. The amount of surfactant in the ink formulation may be within the range of approximately 0% by weight or more, approximately 0.1% by weight or more, approximately 0.2% by weight or more, approximately 0.4% by weight or more, approximately 0.6% by weight or more, approximately 0.8% by weight or more, or approximately 1.0% by weight or less, approximately 1.2% by weight or less, approximately 1.4% by weight or less, approximately 1.6% by weight or less, approximately 1.8% by weight or less, or approximately 2.0% by weight or less, or within the range of 0% to 2% by weight, or 0.1% to 1.8% by weight, or 0.2% to 1.6% by weight, or 0.4% to 1.4% by weight, or 1.0% to 1.2% by weight, or within any range using any two of the above values.

[0053] 2. Desiccant The ink formulations of this disclosure include a desiccant. In this specification, "desiccant" refers to any substance used as a wetting agent or humidifying agent. While not bound by any theory, desiccants are often added to maintain the moisture content of the fixer within a narrow range regardless of humidity fluctuations, and thus prevent clogging of narrow inkjet pen nozzles.

[0054] The desiccants are high-boiling point, water-miscible organic compounds, such as polyols, amides, or polyethers. The desiccants may be water-soluble. Suitable water-soluble desiccants for this purpose include, but are not limited to, heterocyclic ketones (e.g., 2-pyrrolidone, N-methylpyrrolid-2-one, 1,3-dimethylimidazolide-2-one, octylpyrrolidone); glycols (e.g., ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol); glycerol; and diols (e.g., butanediol, pentanediol, hexanediol).

[0055] The desiccant may be present in the ink formulation in an amount of approximately 1% or more by weight, 2% or more by weight, 5% or more by weight, 8% or more by weight, or 10% or less by weight, 12% or less by weight, 15% or less by weight, 18% or less by weight, 20% or less by weight, or any of the endpoints within these ranges.

[0056] 3. Fixative A "fixing solution" or "fixing solution" contains an aqueous vehicle and an effective amount of one or more fixing agents. The fixing agent is a raw material component that initiates a change in the solubility or stability of the colorant, thereby fixing the colorant to the correct position in the printed image. The "effective amount" of fixing agent is the amount effective in achieving improvements in print quality, such as reduced show-through and bleed, increased optical density (OD), saturation, edge clarity, and improved smudge and bleed fastness, compared to an unfixed print. The fixing solution may be formulated to spread well, penetrate quickly, and dry rapidly. The surface tension may be less than about 45 mN / m.

[0057] The fixing agent may be a metal carboxylate salt, such as a metal salt composed of a polyvalent metal ion and a carboxylate ion. Suitable metal carboxylate salts include Ca 2+ Mg 2+ Cu 2+ Divalent metal ions such as Al 3+ , La 3+ , or Fe 3+ Examples include polyvalent metal carboxylic acid salts containing trivalent metal ions.

[0058] Carboxylate ions can be aliphatic monocarboxylic acids having 1 to 6 carbon atoms. Suitable carboxylate ions include acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, pivalic acid, and hexanoic acid.

[0059] The fixing agent is present in the fixing solution composition in an amount within the range of approximately 3% by weight or more, approximately 4% by weight or more, approximately 5% by weight or more, approximately 6% by weight or more, approximately 7% by weight or more, approximately 8% by weight or more, approximately 9% by weight or more, or approximately 10% by weight or less, approximately 11% by weight or less, approximately 12% by weight or less, approximately 13% by weight or less, approximately 14% by weight or less, approximately 15% by weight or less, approximately 16% by weight or less, or any of these endpoints.

[0060] 4. Acid The fixing solution may contain 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 fixing solution composition. Not limited 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.

[0061] The acid helps to adjust the pH of the fixer composition. The pH of the fixer composition may be within the range of approximately 5.0 or higher, approximately 5.5 or higher, approximately 6.0 or higher, or approximately 6.5 or lower, approximately 7.0 or lower, or any of these endpoints.

[0062] In some embodiments, the fixative formulation does not form acid vapor (volatile organic acid) when combined, or forms less than 0.5%. In some other embodiments, the pH of the fixative solution is adjusted to a range suitable for avoiding the fixative solution composition containing more than 0.5% by weight of volatile organic acid.

[0063] 5. Water-based agent The fixer solutions of this disclosure may contain an aqueous vehicle. Where defined herein, the term "aqueous vehicle" means an aqueous mixture to which a fixer is added to form the fixer solution. Suitable aqueous vehicle components may include, but are not limited to, water, cosolvents, surfactants, additives (such as corrosion inhibitors and salts), and / or combinations thereof.

[0064] The aqueous vehicle may comprise a water-soluble organic cosolvent, an additional surfactant, and water. Examples of water-soluble organic cosolvents, though not limited to these, include 2-ethyl-2-hydroxymethyl-1,3-propanediol, glycerol propoxylate, tripropylene glycol, 1-(2-hydroxyethyl)-2-pyrrolidinone, 1-(2-hydroxyethyl)-2-imidazolidinone, and / or combinations thereof.

[0065] 6. Coloring agents The inkjet ink sets of this disclosure may include several embodiments of ink having a fixer composition and a colorant dispersed or dissolved in an ink vehicle, as described above. The inkjet ink set may include at least an inkjet ink composition comprising a colorant dispersed in an ink vehicle, and a fixer comprising one or more surfactants selected from one or more surfactant classes, one or more hygroscopic agents, a metal carboxylate salt as a fixer, and an acid.

[0066] It should be understood that any number of colored ink compositions may be included in the ink set together with a fixer. Furthermore, any desirable combination of colored inks may be used. For example, each of the colored ink compositions may be a different color, or two or more of the inks may be different shades of the same color (i.e., light magenta ink and dark magenta ink). In some embodiments, the inkjet ink set includes four different inks: black ink, yellow ink, cyan ink, and magenta ink. In other embodiments, the inkjet ink set includes 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 embodiments, the inkjet ink set includes a fixer such as those described herein, and inkjet ink compositions selected from black ink, yellow ink, cyan ink, magenta ink, orange ink, red ink, and green ink.

[0067] The colorant for each ink is selected from pigments, dyes, or combinations thereof. In some embodiments, the ink contains a pigment as a colorant. As used herein, “pigment” means colorant particles that are substantially insoluble in the liquid vehicle in which it is used. The pigment may be dispersed using a separate dispersant, or it may be self-dispersible by bonding the dispersant to the surface of the pigment. As used herein, “self-dispersible” generally means a pigment functionalized with a dispersant, such as by chemically bonding the dispersant to the surface of the pigment. The dispersant may be a small molecule, polymer, or oligomer. The pigment includes both self-dispersing pigments and dispersed pigments, such as pigments dispersed by a separate dispersant that is not covalently bonded to the surface. In one example, the pigment is not self-dispersible, and a dispersing aid may be added to the vehicle. In another example, the pigment is self-dispersible and modified to include at least one polymer chemically bonded to the pigment.

[0068] In the example colorants, the chemical composition is classified by number; therefore, "Pigment Blue 29" indicates that it is sodium-aluminum-sulfo-silicate. The numbers do not directly relate to any part of the actual chemical structure; rather, they are assigned chronologically as the pigments were added to the color index code (not when the pigments were discovered).

[0069] Colorants for cyan and / or magenta inks may be a combination of pigments and dyes. Pigments and / or dyes for cyan and magenta colorants may be selected from several commercially available pigments and / or dyes. Not limited examples of pigments suitable for cyan colorants include Pigment Blue 1, Pigment Blue 2, Pigment Blue 3, Pigment Blue 15:3, Pigment Blue 15:4, Pigment Blue 16, Pigment Blue 22, Pigment Blue 29, Bat Blue 4, Bat Blue 6, and / or combinations thereof. Not limited examples of dyes suitable for cyan colorants include triphenylmethane dyes such as Acid Blue 9 and Acid Blue 7, and phthalocyanine dyes such as Direct Blue 199. Examples of pigments suitable for magenta colorants include, but are not limited to, Pigment Red 5, Pigment Red 7, Pigment Red 12, Pigment Red 48, Pigment Red 48, Pigment Red 57, Pigment Red 112, Pigment Red 122, and / or combinations thereof. Examples of dyes suitable for magenta colorants include, but are not limited to, xanthene dyes such as Acid Red 52 and Acid Red 289, γ-acid dyes, H-acid dyes, and / or combinations thereof.

[0070] Colorants for black and / or yellow inks may be dyes or pigments. Examples of dyes suitable 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 derivatives of carbon black are examples of pigments suitable for black inks, but are not limited to these.

[0071] Examples of dyes suitable for yellow colorants include, but are not limited to, AY-17, AY-23, DY-132, Y-104, and / or combinations thereof. PY-74 is an example of a pigment suitable for yellow ink.

[0072] It should be understood that one or more of the inks in an ink set may contain substantially the same colorant and / or substantially the same ink vehicle formulation. For example, an ink set may include yellow ink, cyan ink, and magenta ink, each of which has substantially the same ink vehicle formulation.

[0073] The amount of colorant present in each ink composition is within the range of approximately 2.7% by weight or more, approximately 2.9% by weight or more, approximately 3.0% by weight or more, approximately 3.2% by weight or more, approximately 3.4% by weight or more, or approximately 3.6% by weight or less, approximately 3.8% by weight or less, approximately 4.0% by weight or less, approximately 4.2% by weight or less, approximately 4.4% by weight or less, approximately 4.5% by weight or less, or any of the endpoints of these ranges. However, it should be understood that the amount of colorant filled may be greater or less than the above ranges if desired depending on the application.

[0074] 7. Other additives One or more additives may be incorporated into the fixing agent composition. As used herein, the term “additive” means a component of a liquid that acts to enhance the performance, environmental effect, aesthetic effect, or other similar properties of the liquid. Suitable additives include biocides, scavengers, chelating agents, corrosion inhibitors, marker dyes (e.g., visible, ultraviolet, infrared, fluorescent, etc.), and / or combinations thereof. The fixing agent may include a corrosion inhibitor such as Cobratec® CBT, a carboxybenzotriazole commercially available from PMC Specialties Group, Inc.

[0075] Additives are present in the fixing agent composition in amounts ranging from approximately 0% by weight or more, approximately 0.01% by weight or more, approximately 0.1% by weight or more, approximately 0.2% by weight or more, approximately 0.3% by weight or more, approximately 0.4% by weight or more, or approximately 0.5% by weight or less, approximately 0.6% by weight or less, approximately 0.7% by weight or less, approximately 0.8% by weight or less, approximately 0.9% by weight or less, approximately 1% by weight or less, or any of 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 the pen function, and / or a combination thereof.

[0076] 8. Ink Vehicle Each colorant or combination of colorants is combined with each individual ink vehicle to form one or more inks of an ink set. As defined herein, “ink vehicle” means a vehicle into which a colorant is added to form an ink. A wide variety of ink vehicles may be used with the inks, ink sets, and methods according to the embodiments disclosed herein. Examples of components suitable for an ink vehicle, not limited to these, include water-soluble polymers, anionic polymers, surfactants, solvents, cosolvents, buffers, biocides, scavengers, viscosity modifiers, surfactants, chelating agents, resins, and / or water, and / or combinations thereof.

[0077] Suitable solvents for the ink vehicle include, but are not limited to, glycerol polyoxyethyl ether, tripropylene glycol, tetraethylene glycol, 1-(2-hydroxyethyl)-2-imidazolidinone, 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 fixatives may contain one or more of the following solvents: ethylene glycol, diethylene glycol, triethylene glycol, or 1-propoxy-2-propanol.

[0078] The solvent may be present in the ink vehicle in an amount 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 any of these endpoints.

[0079] The amount and type of solvent used depend, at least in part, on the desired properties of the ink. Therefore, the amount may vary as desired. In some embodiments, a single solvent is used in one or more ink vehicles of the colored inks. Suitable solvents, but are not limited to, include tripropylene glycol, tetraethylene glycol, or 1-(2-hydroxyethyl)-2-pyrrolidone. In other embodiments, the ink contains a mixture of two or more of the solvents listed above.

[0080] Examples, though not limited to them, include cyan ink, magenta ink, yellow ink, and black ink, which contain mixtures 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 any of these endpoints.

[0081] Suitable surfactants include the surfactants of this disclosure, and / or ethoxylated alcohols, fluorinated surfactants, 2-diglycol surfactants, phosphate ester surfactants, diphosphate ester surfactants, alkyl sulfates, alkyl ether sulfates, and / or combinations thereof.

[0082] One or more surfactants may be present in the ink vehicle in amounts of 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.

[0083] The ink vehicle may contain at least one polymer. The polymer for the ink vehicle is generally water-soluble and may be selected from styrene-(meth)acrylic acid copolymer salts, polystyrene-acrylic polymers, polyurethanes, and / or other water-soluble polymer binders, and / or combinations thereof. A suitable polyurethane, though not limited to this example, is a polyurethane commercially available from Dainippon Ink and Chemicals (DIC) in Osaka, Japan.

[0084] The polymer may be present in the ink vehicle in amounts of approximately 0.01% by weight or more, approximately 0.1% by weight or more, approximately 0.5% by weight or more, approximately 1% by weight or more, or approximately 2% by weight or less, approximately 3% by weight or less, approximately 4% by weight or less, or any of these endpoints.

[0085] Additives may also be incorporated into embodiments of the ink vehicle for the ink. Examples, though not limited to them, include fungicides such as Proxel® GXL, which may be added to the ink to protect it from bacterial growth. Other suitable additives, though not limited to them, include buffers, biocides, scavengers, chelating agents, or combinations thereof.

[0086] The ink vehicle contains one or more additives present in amounts within the range of approximately 0% by weight or more, approximately 0.1% by weight or more, approximately 0.2% by weight or more, or approximately 0.3% by weight or less, approximately 0.4% by weight or less, approximately 0.5% by weight or less, or any of these endpoints.

[0087] 9. Manufacturing method Ink formulations can be manufactured by combining a solvent, a surfactant, some additives, and water, and by adjusting the pH to a basic pH. In some embodiments, the pH of the colored ink is in the range of about 8 to about 11. In other embodiments, the pH of the colored ink is in the range of about 8.5 to about 9.5. Next, a colorant and a polymer are added to form the ink composition.

[0088] II.Paint This disclosure provides paint formulations, specifically latex compositions or paint vehicles for semi-gloss and flat interior paint compositions. Latex paint compositions have come to occupy a large portion of the indoor and outdoor paint market due to several advantages compared to organic solvent-based types.

[0089] The coating formulations of this disclosure may comprise a film-forming agent, a binder, one or more surfactants selected from one or more surfactant classes, one or more dryers, one or more pigments, one or more solvents, and water.

[0090] 1. Film-forming agent Film-forming agents are a group of chemical substances that leave a flexible, adhering, and continuous coating on a surface. This film is highly hydrophilic. Film-forming agents encompass a broad group of chemical substances that can be broadly divided into two categories: natural and synthetic.

[0091] Natural film-forming agents include oils, rosin, carbohydrates, and egg whites. Examples of such natural film-forming agents include cyclic oligoterpenes, polyterpenes, and shellac (such as starch and cellulose).

[0092] Synthetic film-forming agents include condensation polymer materials, addition polymer materials, and polymer resins. Examples of synthetic film-forming agents include crosslinking materials such as alkyd resins, polyesters, polyamides / imides, silicone resins, and phenolic resins, as well as melamine resins, urea resins, polyurethanes, epoxy resins, polyolefins, polyvinyl resins, and polyacrylic resins.

[0093] Latex coatings often contain synthetic film-forming agents such as polyacrylate resins and alkyd resins, as will be discussed further below. a. Latex emulsion Two types of emulsions commonly used to formulate latex paints are all-acrylic systems, such as those using copolymers of methyl methacrylate, butyl acrylate, or 2-ethylhexyl acrylate with a small amount of acrylic acid as desired, and vinyl acetate formulations, usually combined with a small amount of lower alkyl acrylate, such as 2-ethylhexyl acrylate, methyl methacrylate, or butyl acrylate. Until now, all-acrylic systems have been used for high-quality paints because this emulsion has provided good water resistance, desired leveling properties, film hardness, durability, and scrubability. Vinyl acetate-acrylic copolymer systems are used to formulate interior flat and semi-gloss paints and exterior house paints. Vinyl acetate-butyl acrylate latex provides a coating with excellent toughness, scrubability, and durability, while vinyl acetate-dibutyl maleate emulsion has good abrasion resistance and flexibility in addition to durability.

[0094] Wet adhesion, i.e., the property of adhering to an already painted and aged surface under wet or humid conditions, has been imparted to both acrylic and vinyl acetate copolymers by polymerizing wet-adhesion monomers into the copolymer. Typically, these monomers have a terminal olefinic unsaturated group at one end and a terminal ureid or urea functional group at the other end. While these monomers increase the emulsion's ability to adhere to an already painted film under humid conditions, they can sometimes be difficult to polymerize into systems, particularly acrylic systems, and to achieve other desired properties of the paint. Therefore, wet adhesion of a paint vehicle is imparted by blending different types of acrylic polymer emulsions to obtain the desired overall properties of the paint vehicle, namely durability, wet adhesion, washability, flexibility, good leveling, abrasion resistance, toughness, etc.

[0095] Suitable emulsions include vinyl acetate latex. For interior and exterior applications, vinyl acetate can be copolymerized with monomers copolymerizable thereto, namely C1-C6 esters of acrylic and methacrylic acids, including lower alkyl acrylates such as methyl methacrylate, ethyl acrylate, butyl acrylate, and 2-ethylhexyl acrylate; olefins such as ethylene; alkyl esters of alpha-beta unsaturated dicarboxylic acids such as dibutyl maleate, dibutyl fumarate, dioctyl maleate, and dibutyl itaconate; vinyl chloride, vinyl esters such as vinyl butyrate and vinyl propionate; vinyl ethers such as methyl vinyl ether and n-butyl vinyl ether; and unsaturated carboxylic acids and amides such as acrylic and methacrylic acid, acrylamide, and methacrylamide.

[0096] To achieve the wet-adhesion properties required for most coating applications, wet-adhesion monomers may be copolymerized with vinyl acetate to form vinyl acetate terpolymers. These may also be copolymerized with other monomers and blended with vinyl acetate copolymers to impart wet-adhesion properties. As used herein, "wet-adhesion monomer" is understood to mean a monomer having an allyl or acrylic unsaturated group at one end of the molecule and a pendant urea or acyl and cyclic ureide functional group at the other end.

[0097] Latex may be present in the formulation in amounts of approximately 40% or more by weight, approximately 45% or more by weight, approximately 50% or more by weight, approximately 55% or more by weight, or approximately 60% or less by weight, approximately 65% ​​or less by weight, approximately 70% or less by weight, or any of these endpoints, as a percentage of the total formulation.

[0098] 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 any of these endpoints.

[0099] Lower alkyl acrylates or olefins may be present in the copolymer. The comonomers may be present in amounts of 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 17% or less by weight, about 20% or less by weight, or any of these endpoints as a percentage of the polymer weight.

[0100] Wet-adhesion monomers, such as monomers having an allyl or acrylic unsaturated group at one end of the molecule and a pendant urea or acyl and cyclic ureid functional group at the other end, may be included in the coating formulation. Wet-adhesion monomers may be present in the coating formulation in amounts of about 0.2% or more by weight of the polymer, about 0.4% or more by weight, about 0.8% or more by weight, about 1.0% or more by weight, about 1.2% or more by weight, or about 1.4% or less by weight, about 1.6% or less by weight, about 1.8% or less by weight, about 2.0% or less by weight, about 2.2% or less by weight, about 2.4% or less by weight, about 2.6% or less by weight, or any of the ranges using these endpoints, as a percentage of the polymer weight.

[0101] With respect to tetrapolymers, suitable compositions may include vinyl chloride, vinyl acetate, ethylene, and wet-adhesion monomers. Vinyl chloride may be present in amounts of approximately 25% or more by weight of the total polymer, approximately 30% or more by weight, approximately 35% or more by weight, approximately 40% or more by weight, approximately 45% or more by weight, or approximately 50% or less by weight, approximately 55% or less by weight, approximately 60% or less by weight, approximately 65% ​​or less by weight, or within any of the ranges using these endpoints.

[0102] Vinyl acetate may be present in amounts of approximately 30% or more by weight of the total polymer, approximately 35% or more by weight, approximately 40% or more by weight, approximately 45% or more by weight, or approximately 50% or less by weight, approximately 55% or less by weight, approximately 60% or less by weight, approximately 65% ​​or less by weight, or within any of the ranges using these endpoints.

[0103] Ethylene may be present in amounts of about 10% or more by weight of the total polymer, about 11% or more by weight, about 12% or more by weight, or about 13% or less by weight, about 14% or less by weight, about 15% or less by weight, or any of these endpoints.

[0104] The wet-adhesion monomer may be present in amounts of about 0.2% or more by weight of the polymer, about 0.4% or more by weight, about 0.8% or more by weight, about 1.0% or more by weight, about 1.2% or more by weight, or about 1.4% or less by weight, about 1.6% or less by weight, about 1.8% or less by weight, about 2.0% or less by weight, about 2.2% or less by weight, about 2.4% or less by weight, about 2.6% or less by weight, or within any range using these endpoints.

[0105] b. Alkyd resin The coating formulation may contain one or more binders. Suitable binders include various types of alkyd resins. Exemplary alkyd resins include those having short, medium, long, and very long oil chains. The term “alkyd resin” also includes alkyds modified with other resins such as acrylic, epoxy, phenolic, urethane, polystyrene, silicone, rosin, and rosin ester alkyds, as well as bioalkyds such as Setal 900 SM-90, in which the polyester segment is derived from renewable acids and esters.

[0106] The paint 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 any of these endpoints, based on the total weight of the composition.

[0107] 2. Surfactants The paint formulation of the present invention comprises one or more surfactants, also referred to as a surfactant system. The surfactant system comprises at least one surfactant, which may be an amphoteric surfactant, a zwitterionic surfactant, a cationic surfactant, or a nonionic surfactant, and optionally at least one other surfactant, which may be an amphoteric surfactant, a zwitterionic surfactant, a cationic surfactant, a nonionic surfactant, or a combination thereof. The surfactant system is present in the paint formulation to assist in the stabilization of the emulsion.

[0108] The surfactants suitable for use in the paint formulations of this disclosure include one or more surfactants of formula I or II and / or cosurfactants.

[0109] [ka]

[0110] In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, and optionally the C1-C6 alkyl group may comprise one or more atoms from oxygen, nitrogen, or sulfur, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid and C1-C bonded to further surfactant molecules having the structure represented by formula I 12 Further surfactant molecules of formula I may be selected from the group consisting of linkers, and these may be identical or different from the surfactant molecules of formula I; n and z may be independently selected from any integer between 1 and 12; m may be any integer from 1 to 12; and X may be selected from the group consisting of chlorides, bromides, and iodides.

[0111] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, where the second molecule of formula I is the same as the first molecule of formula I.

[0112] More specifically, R 3 The following set of formulas may be selected.

[0113] [ka]

[0114] In particular, a suitable surfactant or co-surfactant may include one or more of the surfactants 1 to 12 described herein. The total amount of one or more surfactants in the paint formulation may be within the range of approximately 0.5% by weight or more, approximately 1% by weight or more, approximately 2% by weight or more, or approximately 3% by weight or less, approximately 4% by weight or less, approximately 5% by weight or less, or any of these endpoints.

[0115] 3. Hair dryer The paint formulation may contain one or more dryers. A dryer is a catalyst used to accelerate the drying process. A suitable dryer may contain an oxidation catalyst such as a cobalt or manganese salt, a polymerization catalyst such as a zirconium salt, and / or an auxiliary catalyst such as a calcium salt that controls film formation. The dryer can completely dry the paint within a few hours, such as within 3 hours, within 2 hours, or less, after application to the surface. The cobalt or manganese ester is an oxidation catalyst that plays a role in initiating the oxidation process, C6-C 19 This includes esters of branched-chain fatty acids. Examples include cobalt 2-ethylhexanoate, cobalt propionate, cobalt neodecanoate, cobalt naphthenate, a cobalt-embedded polymer product called ECOS ND15 available from Umicore, manganese octanoate, and a manganese-amine complex called Nuodex Drycoat available from Huntsman.

[0116] The dryer composition may be included in the paint 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 any of the endpoints within this range.

[0117] 4. Pigments Pigments used in aqueous paint compositions typically include opaque pigments that impart opacity or concealment to the paint film. The paint formulations of this disclosure may include one or more pigments for coloring the composition and / or for imparting opacity to the composition. As used herein, pigments include both inorganic metal oxides and organic coloring pigments. Suitable pigments include metal oxides such as titanium dioxide 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 coloring pigments include phthalocyanine blue (alpha and beta), dinitroaniline orange (PO-5), perylene red, toluidine red (PR-3), diallylide yellow (PY-12, 13), and quinacridone red (PV-19).

[0118] Pigments may be included in the paint composition in amounts ranging from about 0% by weight or more, 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, about 30% by weight or less, or any of these endpoints.

[0119] 5. Solvent Paint formulations may contain mineral spirits and one or more aqueous or organic solvents such as 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 (an aliphatic solvent with a flash point of 140°F). Aromatic solvents include xylene, toluene, Aromatic 100, and other suitable aromatic solvents. The term "mineral spirits," also known as "white spirits," refers to C7-C 12 The composition includes a mixture of aliphatic and alicyclic hydrocarbons, and in more detailed embodiments, 15% to 20% by weight or less of C7 to C7 based on the total weight of the composition. 12Contains aromatic hydrocarbons. Mineral spirits include paraffins, cycloparaffins, and mixtures or blends of aromatic hydrocarbons. Typical mineral spirits have a boiling point range of approximately 150°C to 220°C, are generally colorless and transparent liquids, are chemically stable and non-corrosive, and have a light odor. Exemplary mineral spirits include Low Aromatic White Spirits (LAWS) such as Shell Sol 15 (CAS 64742-88-7) and Shell Sol H (CAS 64742-82-1). The term "alcohol" refers to C1-C 12 C1-C alcohols including linear and branched alcohols 12 Alcohols are included and intended to be included. Exemplary alcohols include triethylene glycol (CAS 112-27-6) and diethylene glycol ethyl ether (CAS 111-90-0). In more detailed embodiments, the coating composition comprises a solvent selected from the group consisting of xylene, mineral spirits, alcohols, water, and combinations thereof.

[0120] The amount of solvent in the paint formulation may be approximately 5% by weight or more, approximately 10% by weight or more, approximately 15% by weight or more, approximately 17% by weight or more, approximately 20% by weight or more, approximately 25% by weight or more, or approximately 30% by weight or less, approximately 40% by weight or less, approximately 60% by weight or less, or within any of these endpoints.

[0121] 6. Other additives The paint formulation may further include one or more additives, such as fillers, pigments, surfactants, stabilizers, thickeners, emulsifiers, texturers, adhesion promoters, biocides, flow promoters, dispersants, and additives for modifying viscosity or finish appearance.

[0122] The additive may be included in the paint formulation in amounts of approximately 0.1% by weight or more, approximately 0.5% by weight or more, approximately 1.0% by weight or more, approximately 1.5% by weight or more, or approximately 2.0% by weight or less, approximately 5.0% by weight or less, approximately 10.0% by weight or less, approximately 20% by weight or less, approximately 25% by weight or less, approximately 30% by weight or less, or any of the following endpoints.

[0123] The paint formulation 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.

[0124] The paint formulation may contain one or more additives selected from the group consisting of surfactants, stabilizers, thickeners, emulsifiers, texturers, adhesion promoters, biocides, and additives for modifying viscosity or finish appearance.

[0125] 7. Manufacturing method Paint formulations can be synthesized by starting with a standard premix of protective colloids, surfactants, and oxidizing agents. Monomers, followed by additional surfactants and reducing agents, may then be added.

[0126] Examples of protective colloids include hydroxyethylcellulose, polyvinyl alcohol, casein, hydroxyethyl starch, and carboxymethylcellulose. The protective colloid may be added in amounts of approximately 0.05% by weight or more, approximately 0.1% by weight or more, approximately 0.5% by weight or more, approximately 1.0% by weight or more, approximately 1.5% by weight or more, approximately 2% by weight or more, or approximately 2.5% by weight or less, approximately 3.0% by weight or less, approximately 3.5% by weight or less, approximately 4.0% by weight or less, approximately 4.5% by weight or less, or any of the following endpoints, relative to the weight of the monomer used in the synthesis.

[0127] Free radical initiation catalysts used to induce polymerization are generally called redox catalysts. Redox catalysts, as is well known, contain an oxidizing agent and a reducing agent. The oxidizing and reducing components may be any of the components conventionally used in vinyl acetate emulsion polymerization, such as hydrogen peroxide, potassium persulfate, and t-butyl peroxypivalate. Preferred reducing agents are ammonium iron(II) sulfate and sodium or zinc formaldehyde sulfoxylate.

[0128] A premix can be formed by adding water, a protective colloid such as hydroxyethylcellulose, and a free radical initiating oxidizing agent in conventional amounts to a primary vessel. Next, about 0-70% of the total surfactant to be used can be added to the primary vessel and mixed therein. The remaining surfactant can be mixed with the monomer in a secondary vessel or added separately. In either case, it can be added after a certain delay time. To induce polymerization, monomers and reducing agents can be added to the primary vessel over a certain period of time and at a certain rate so that the unreacted vinyl acetate in the primary vessel is maintained at about 3-5% by weight of the emulsion or latex. After all monomers have been added to the primary vessel, the residual vinyl acetate is subsequently reduced to less than 0.5% by adding additional oxidizing and reducing agents. At the end of polymerization, the pH can be adjusted to about 5.5 by adding a base such as ammonium hydroxide.

[0129] Regarding the polymerization procedure, protective colloids, particularly cellulose ethers, are used to maintain the stability of the emulsion. Higher levels of colloid tend to improve stability and further increase particle size. Surfactants also contribute stability to the emulsion. However, in contrast to colloids, surfactants tend to decrease particle size when present during initial polymerization, and tend to exhibit a better particle size effect when added with a delay. By combining protective colloids and surfactants, particle size optimization can be achieved.

[0130] Stirring is another variable that can affect particle size in a polymer emulsion. Stirring should be gentle so that proper heat transfer can be achieved and the stability of the product can be maintained. Vigorous stirring should be avoided. With regard to particle size control, if larger particles are desired, the stirring speed may be reduced, and if smaller particles are required, the degree of stirring may be increased. If stirring cannot be modified, adjustments may be made with surfactants or protective colloids.

[0131] III. Adhesive Formulations The disclosure further provides adhesive formulations. The adhesive formulations of the disclosure may be used in the manufacture of wood-based boards such as plywood, backing boards, blackboards, fiberboards, OBS boards, or homogeneous materials.

[0132] The adhesive formulations of this disclosure may comprise a resin, a filler, a solvent, and one or more surfactants selected from one or more classes of surfactants. 1. Resin The resin is present in the adhesive formulation to function as the adhesive itself. Suitable resins may include phenol-formaldehyde 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), MUFP (modified urea-formaldehyde polymer), PF (phenol-formaldehyde), or derivatives or mixtures thereof, or equivalents.

[0133] The resin may be present in the adhesive formulation in amounts of approximately 40% by weight or more, approximately 45% by weight or more, approximately 50% by weight or more, approximately 55% by weight or more, or approximately 60% by weight or less, approximately 65% ​​by weight or less, approximately 70% by weight or less, approximately 75% by weight or less, approximately 80% by weight or less, or any of these endpoints.

[0134] 2. Filler As used herein, “filler” means a known filler or hardener alone, or a mixture thereof. The hardener causes the adhesive to harden at the time of application, i.e., in the process of manufacturing wood-based boards, often preferably with compression heat. Suitable fillers may include starch, wheat flour, chalk, sodium carbonate, potassium carbonate, calcium carbonate, ammonium sulfate, wood flour, quebracho, or derivatives thereof, or mixtures thereof, or equivalents. Quebracho refers to a hardwood from a certain South American hardwood. As used herein, “chalk” refers to loosely structured, lightweight, and brittle limestone.

[0135] The filler may be present in the adhesive composition in an amount of about 5 wt% or more, about 10 wt% or more, about 15 wt% or more, or about 20 wt% or less, about 25 wt% or less, about 30 wt% or less, or within any range using these endpoints.

[0136] 3. Solvent The adhesive formulation may include a solvent such as water. The water may be obtained from outside the process or it may be recycled water within the process, i.e., process wash water. As another option, the solvent may be an organic solvent.

[0137] The solvent may be present in the adhesive composition in an amount of about 0 wt% or more, about 5 wt% or more, about 10 wt% or more, about 15 wt% or more, about 20 wt% or more, or about 25 wt% or less, about 30 wt% or less, about 35 wt% or less, about 40 wt% or less, or within any range using these endpoints.

[0138] 4. Surfactant One or more surfactants may be included in the adhesive formulation as a foaming agent for the explicit purpose of promoting foaming. Surfactants suitable for use in the adhesive formulations of the present disclosure include one or more surfactants of Formula I or II and / or co-surfactants,

[0139] [Chemical formula]

[0140] Wherein, R 1 and R 2 may be the same or different and each contains at least one group selected from the group consisting of C1-C6 alkyl, and optionally, the C1-C6 alkyl may contain one or more of oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3is selected from the group consisting of alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 alkyl benzoic acid, and a C1-C linker bonded to a further surfactant molecule having the structure represented by formula I 12 and may be selected from the group consisting of a linker, and the further surfactant molecule of formula I is the same as or different from the surfactant molecule of formula I; n and z may independently be selected from any integer from 1 to 12; m may be any integer from 1 to 12; and<000,0807>X may be selected from the group consisting of chloride, bromide, and iodide.

[0141] Specifically, R 3 is C2-C 10 alkenyl, C2-C 10 alkynyl, C2-C 12 ester, C1-C<"0000097">hydroxyl, benzyl, C2-C 12 alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C5 alkyl benzoic acid, and a 3-carbon linker bonded to a second molecule of formula I, and the second molecule of formula I is the same as the first molecule of formula I.

[0142] More specifically, R 3 may be selected from the group consisting of the following formulas.<"0000814">

[0143]

Chemical formula

[0144] In particular, suitable surfactants or co-surfactants may include any one or more of surfactants 1-12 described herein.<"0000824">The adhesive formulation may contain one or more surfactants in amounts of approximately 0.1% by weight or more, approximately 0.5% by weight or more, approximately 1% by weight or more, approximately 2% by weight or more, approximately 3% by weight or more, approximately 4% by weight or more, or approximately 5% by weight or less, approximately 6% by weight or less, approximately 7% by weight or less, approximately 8% by weight or less, approximately 9% by weight or less, approximately 10% by weight or less, or any of the following endpoints.

[0145] 5. Other additives The adhesive formulation may contain one or more additional compatible raw material components. These additional raw material components may include one or more additional surfactants, not intended solely for foaming purposes, such as the surfactants of this disclosure. 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 any of these endpoints.

[0146] The adhesive composition may also include a catalyst. 6. Manufacturing method Adhesive formulations can be manufactured as emulsions. To produce an emulsion, liquid components may be mixed together, and this mixture may be heat-treated at a relatively high temperature (above 40°C).

[0147] IV. Paint Remover This disclosure also provides formulations for paint removers. These compositions can be used to remove adhesives, sealants, and other organic coatings such as enamels, varnishes, or lacquers, or other organic coatings, from a variety of substrates, including metal substrates such as aluminum and aluminum alloys. Generally, the composition is in contact with the surface for a sufficient amount of time to cause blistering in the polymer coating, after which the blistered coating can be removed with an abrasive. Alternatively, the coating can be removed by spraying water onto the blistered coating to lift the blistered coating from the surface.

[0148] The paint stripping formulations of this disclosure 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.

[0149] 1. Dichloroethylene The peeling agent may contain dichloroethylene (1,1-dichloroethylene, cis-1,2-dichloroethylene, trans-1,2-dichloroethylene, or a mixture thereof).

[0150] Dichloroethylene may be present in the peeling agent in amounts of approximately 55% by weight or more, approximately 57% by weight or more, approximately 59% by weight or more, or approximately 61% by weight or less, approximately 63% by weight or less, approximately 65% ​​by weight or less, or any of the endpoints within these ranges.

[0151] 2. Surfactants Surfactants may be included in stripping formulations for the purpose of increasing the solubility of certain components. Surfactants suitable for use in the stripping formulations of this disclosure include one or more surfactants and / or cosurfactants of formula I or II,

[0152] [ka]

[0153] In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, and optionally the C1-C6 alkyl group may comprise one or more atoms from oxygen, nitrogen, or sulfur, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid and C1-C bonded to further surfactant molecules having the structure represented by formula I 12 Further surfactant molecules of formula I may be selected from the group consisting of linkers, and these may be identical or different from the surfactant molecules of formula I; n and z may be independently selected from any integer between 1 and 12; m may be any integer from 1 to 12; and X may be selected from the group consisting of chlorides, bromides, and iodides.

[0154] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, where the second molecule of formula I is the same as the first molecule of formula I.

[0155] More specifically, R 3 The following set of formulas may be selected.

[0156] [ka]

[0157] In particular, a suitable surfactant or co-surfactant may include one or more of the surfactants 1 to 12 described herein. The surfactant may be present in the stripping formulation in an amount within the range of approximately 1% by weight or more, approximately 2% by weight or more, approximately 3% by weight or more, approximately 4% by weight or more, approximately 5% by weight or more, or approximately 6% by weight or less, approximately 7% by weight or less, approximately 8% by weight or less, approximately 9% by weight or less, approximately 10% by weight or less, or any of these endpoints.

[0158] 3. Cosolvent Cosolvents may be used to enhance the swelling of the paint of interest. The release agents of this disclosure may include such cosolvents. Suitable solvents include aromatic alcohols and aromatic ethers such as diphenoxybenzene, propoxybenzene, methoxybenzene, ethoxybenzene, benzyl ether, diphenyl ether, cyclopentanol, naphthalenol, phenylcarbinal, tolyl alcohol, mellityl alcohol, and other aromatic alcohols containing a hydroxyl group in the side chain of the aromatic ring. Other suitable solvents include aliphatic alcohols, ethanol, propanol, butanol, pentanol, hexanol, and alcohols having up to 12 carbon atoms. Such cosolvents are generally considered environmentally friendly and non-toxic and may be effective cosolvents that do not require additional activators for release agents containing 1,2-dichloroethylene.

[0159] Aromatic alcohols and aromatic ethers may be present in the stripping formulation in amounts of approximately 10% or more by weight, approximately 11% or more by weight, approximately 12% or more by weight, approximately 13% or more by weight, approximately 14% or more by weight, approximately 15% or more by weight, or approximately 16% or less by weight, approximately 17% or less by weight, approximately 18% or less by weight, approximately 19% or less by weight, approximately 20% or less by weight, or any of these endpoints.

[0160] Aliphatic alcohols may be present in the stripping formulation in amounts of approximately 1% by weight or more, approximately 2% by weight or more, approximately 3% by weight or more, approximately 4% by weight or more, approximately 5% by weight or more, or approximately 6% by weight or less, approximately 7% by weight or less, approximately 8% by weight or less, approximately 9% by weight or less, approximately 10% by weight or less, or any of these endpoints.

[0161] 4. Corrosion inhibitor The release formulation of the present disclosure may include a corrosion inhibitor. Suitable corrosion inhibitors may include benzimidazole, benzazole, benzoxazole, and mixtures of these corrosion inhibitors, and further may include triazoles such as benzotriazole and tolyltriazole.

[0162] The corrosion inhibitor may be included in the release formulation in an effective amount of about 0 wt% or more, about 1 wt% or more, about 2 wt% or more, about 3 wt% or more, about 4 wt% or more, about 5 wt% or more, or about 6 wt% or less, about 7 wt% or less, about 8 wt% or less, about 9 wt% or less, about 10 wt% or less, or within any range using these endpoints.

[0163] 5. Wax The release formulation of the present disclosure may include wax. Suitable waxes may include paraffin wax. To facilitate mixing with other components of the release formulation, the wax may be dissolved in a solvent prior to mixing with other components. A solvent that is substantially non-polar or lipophilic may be used for this purpose. Suitable solvents may include aromatic and aliphatic hydrocarbons, such as benzene, toluene, xylene, hexane, cyclohexane, heptane, octane, and similar straight-chain and branched-chain hydrocarbons, and mixtures thereof. Fractions from the distillation of petroleum mineral spirits, and various mixtures of these solvents may also be included.

[0164] The wax may be present in the release formulation in an amount of about 1.0 wt% or more, 1.5 wt% or more, 2.0 wt% or more, 2.5 wt% or more, or 3.0 wt% or less, 3.5 wt% or less, 4.0 wt% or less, 4.5 wt% or less, or 5.0 wt% or less, or within any range using these endpoints.

[0165] 6. Thickener The release formulations of this disclosure may include thickeners. In applications where vertical surfaces are to be treated with the formulation, thickeners may be used to maintain the formulation on the coating surface for a sufficiently long time to loosen the coating. Suitable thickeners may include cellulose such as ethylcellulose, ethylhydroxyethylcellulose, and methylcellulose; clay such as colloidal silica and bentonite; starch colloidal alumina; or gum arabic.

[0166] The thickening agent may be present in the release agent in amounts of 0% or more by weight, 1.0% or more by weight, 1.5% or more by weight, 2.0% or more by weight, 2.5% or more by weight, or 3.0% or less by weight, 3.5% or less by weight, 4.0% or less by weight, 4.5% or less by weight, or 5.0% or less by weight, or any of the endpoints within these ranges.

[0167] 7. Solvent The stripping formulations of this disclosure may include organic solvents and additional solvents such as water. The organic solvent may be present in the stripping agent in an amount of approximately 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 any of the following endpoints.

[0168] Water may be present in the peeling agent in amounts of approximately 1% by weight or more, approximately 5% by weight or more, approximately 8% by weight or more, approximately 10% by weight or more, or approximately 12% by weight or less, approximately 15% by weight or less, approximately 18% by weight or less, approximately 20% by weight or less, or any of the endpoints within these ranges.

[0169] 8.How to use The exfoliating formulations of this disclosure are generally applied to surfaces to be exfoliated by conventional methods, i.e., the composition is applied to a brush or other applicator and then to the surface to be exfoliated. Alternatively, the formulation may be sprayed onto the surface using a spraying system, such as a system that takes advantage of the thixotropic properties of the formulation on a vertical panel.

[0170] VI. Surfactants This disclosure provides surfactants for use in inks, paints, adhesives, and paint removers, in the form of amino acid siloxane derivatives. The amino acids may be natural or synthetic, or obtained from the ring-opening reaction of lactams such as caprolactam. The compounds of this disclosure have been shown to possess surface-active properties and can be used, for example, as surfactants and wetting agents. In particular, surfactants for use in ink, paint, or adhesive products are provided in the form of surfactant molecules of formula I or II.

[0171] [ka]

[0172] In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, and optionally the C1-C6 alkyl group may comprise one or more atoms from oxygen, nitrogen, or sulfur, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid and C1-C bonded to further surfactant molecules having the structure represented by formula I 12 Further surfactant molecules of formula I may be selected from the group consisting of linkers, and these may be identical or different from the surfactant molecules of formula I; n and z may be independently selected from any integer between 1 and 12; m may be any integer from 1 to 12; and X may be selected from the group consisting of chlorides, bromides, and iodides.

[0173] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, where the second molecule of formula I is the same as the first molecule of formula I.

[0174] More specifically, R 3 The following set of formulas may be selected.

[0175] [ka]

[0176] Formulations comprising at least one surfactant of formula I or II for use in various inks, paints, or adhesive products are disclosed above. The following disclosures of compounds of formula I and II apply to compounds of formula I and II in any of the uses and formulations shown and disclosed herein.

[0177] Further compounds provided in this disclosure are R 1 and R 2 It is a compound of formula I in which is methyl. Other compounds provided by this disclosure are compounds of formula I, where n and / or z are 5.

[0178] As used herein, the phrase “n may be an integer between 1 and 12” means that n may be equal to 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and / or 12.

[0179] As used herein, the term "C1-C6 alkyl" means a straight-chain or branched-chain alkyl group containing 1, 2, 3, 4, 5, and / or 6 carbons. As used herein, the term "C1-C6 linker" means a straight-chain or branched-chain alkyl chain containing 1, 2, 3, 4, 5, and / or 6 carbons.

[0180] As used herein, the term "C2-C 10 alkenyl" means a straight-chain or branched-chain alkenyl group containing 2, 3, 4, 5, 6, 7, 8, 9, and / or 10 carbons.

[0181] As used herein, the term "C2-C 10 alkynyl" means a straight-chain or branched-chain alkynyl group containing 2, 3, 4, 5, 6, 7, 8, 9, and / or 10 carbons.

[0182] As used herein, the term "C2-C 12 ester" means a straight-chain or branched-chain ester group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and / or 12 carbons.

[0183] As used herein, the term "C2-C 12 alkoxyalkyl ether" means a straight-chain or branched-chain alkoxyalkyl ether group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and / or 12 carbons.

[0184] As used herein, the term "C1-C 10 hydroxyl" means a hydroxyl attached to a straight-chain or branched-chain alkyl group containing 1, 2, 3, 4, 5, 6, 7, 8, 9, and / or 10 carbons.

[0185] As used herein, the phrase “C3-C8 carboxylic acid” means a carboxylic acid group bonded to a linear or branched alkyl group containing 3, 4, 5, 6, 7, and / or 8 carbon atoms.

[0186] As used herein, "C1~C 10 The phrase "alkylbenzoic acid" means a benzoic acid group bonded to a linear or branched alkyl group containing 1, 2, 3, 4, 5, 6, 7, 8, 9, and / or 10 carbon atoms.

[0187] As used herein, the phrase “n and z may be independently selected from any integers between 1 and 12” means that n and z may independently be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and / or 12.

[0188] As used herein, the phrase “m may be any integer between 1 and 12” means that m may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and / or 12.

[0189] As used herein, the phrase “q may be any integer between 1 and 10” means that q may be 1, 2, 3, 4, 5, 6, 7, 8, 9, and / or 10.

[0190] One specific compound provided by this disclosure and 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-oxohexane-1-aminium bromide, which has the following formula:

[0191] [ka]

[0192] The second specific compound provided by this disclosure and 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-oxohexane-1-aminium bromide, which has the following formula:

[0193] [ka]

[0194] A third specific compound provided by this disclosure and 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-oxohexane-1-aminium iodide, which has the following formula:

[0195] [ka]

[0196] The fourth specific compound provided by this disclosure and 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-(propa-2-in-1-yl)hexane-1-aminium bromide, which has the following formula:

[0197] [ka]

[0198] The fifth specific compound provided by this disclosure and 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-oxohexane-1-aminium bromide, which has the following formula:

[0199] [ka]

[0200] The sixth specific compound provided by this disclosure and 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-oxohexane-1-aminium bromide, which has the following formula:

[0201] [ka]

[0202] The seventh specific compound provided by this disclosure and 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-oxohexane-1-aminium iodide, which has the following formula:

[0203] [ka]

[0204] The eighth specific compound provided by this disclosure and 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-oxohexane-1-aminium iodide, which has the following formula:

[0205] [ka]

[0206] The specific compound 9 provided by this disclosure and 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-oxohexane-1-aminium bromide, which has the following formula:

[0207] [ka]

[0208] A specific compound provided in this disclosure, 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 It is -tetramethylpropane-1,3-diaminium dibromide and has the following formula.

[0209] [ka]

[0210] A further group of specific compounds provided herein and referred to herein as surfactants 11-12 have the following general formulas:

[0211] [ka]

[0212] In the formula, q may be an integer between 1 and 10. The 11th specific compound provided by this disclosure and 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-oxohexane-1-aminium bromide, which has the following formula:

[0213] [ka]

[0214] The twelfth specific compound provided by this disclosure and 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-oxohexane-1-aminium bromide, which has the following formula:

[0215] [ka]

[0216] These compounds can be synthesized by various methods. One such method involves reacting an amino acid, such as an N-alkylated or N-acylated amino acid, with a siloxane to convert the C-terminus of the amino acid into a desired siloxane derivative. For example, the N-terminus of an amino acid can be further alkylated to obtain a quaternary amine.

[0217] The amino acids may be natural or synthetic amino acids, or they may be derived from the ring-opening reaction of lactams such as caprolactam. The ring-opening reaction may be either acid-catalyzed or alkali-catalyzed, and an example of an acid-catalyzed reaction is shown in Scheme 1 below.

[0218] [ka]

[0219] An amino acid may have at least one or as many as twelve carbon atoms between its N-terminus and C-terminus, such as one, two, three, four, five, six, seven, eight, nine, ten, eleven, or twelve carbon atoms. The alkyl chain may be branched or linear. Nitrogen, oxygen, or sulfur may be interposed in the alkyl chain. The alkyl chain may be further substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carboxyl, and carboxylate. The N-terminal nitrogen may be acylated or alkylated with one or more alkyl groups. For example, the amino acid may be 6-(dimethylamino)hexanoic acid.

[0220] The siloxane may be substituted with one or more alkoxy groups, such as methoxy, ethoxy, isopropoxy, or tertiary butoxy. The siloxane may be further substituted with one or more alkyl groups, such as propyl, in which case the alkyl group may be further substituted with a suitable functional group, such as nitrogen, that enables the coupling of the siloxane to an amino acid. For example, the siloxane may be 3-aminopropyltris(trimethylsiloxy)silane.

[0221] Siloxane derivatives of amino acids can be synthesized as shown in Scheme 2 below. As shown, 6-aminohexanoic acid can be alkylated at the N-terminus by treatment with formaldehyde in formic acid under reflux to obtain 6-(dimethylamino)hexanoic acid. This free carboxylic acid is then coupled with 3-aminopropyl(trismethylsiloxy)silane in refluxed toluene to obtain the desired siloxane derivative.

[0222] [ka]

[0223] The N-terminal nitrogen can be further derivatized to modify or improve water solubility and surface activity properties. A sample synthesis scheme is shown in Scheme 3 below, in which case the N-terminal nitrogen is alkylated to obtain a quaternary amine.

[0224] [ka]

[0225] Suitable alkylating agents include, for example, benzyl bromide, ethyl bromo, allyl iodide, propargyl bromide, 1-bromo-2-(2-methoxyethoxy)ethane, bromophosphonate, 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 may be linked by treating the N-terminal nitrogen with a bifunctional alkylating agent such as 1,3-dibromopropane.

[0226] The compounds of this disclosure exhibit surface activity properties. These properties can be measured and expressed by various methods. One way to express a surfactant is by the critical micelle concentration (CMC) of the molecule. CMC can be defined as the concentration of surfactant that forms micelles, at concentrations higher than this, all additional surfactant is incorporated into the micelles.

[0227] As the surfactant concentration increases, the surface tension decreases. When the surface is completely covered with surfactant molecules, micelles begin to form. This point represents the CMC, and thus the minimum surface tension. Adding more surfactant does not further affect the surface tension. The CMC can therefore be measured by observing the change in surface tension as a function of surfactant concentration. One such method for measuring this value is the Wilhelmie plate method. A Wilhelmie plate is typically a thin iridium-platinum plate attached to a balance by wire and positioned perpendicular to the air-liquid interface. Using the balance, the force acting on the plate due to wetting is measured. Then, using this value, the surface tension (γ) is calculated according to Equation 1: Equation 1: γ = F / l cosθ In the formula, l is equal to the wet perimeter (2w + 2d, where w and d are the thickness and width of the plate, respectively), and for cosθ, the contact angle between the liquid and the plate is assumed to be 0 if there are no existing literature values.

[0228] Another parameter used to evaluate the performance of surfactants is dynamic surface tension. Dynamic surface tension is the value of surface tension over time at a particular surface or interface. In the case of a liquid to which a surfactant has been added, this may differ from the equilibrium value. Immediately after the surface is formed, the surface tension is equal to that of the pure liquid. As mentioned above, surfactants decrease surface tension, so the surface tension decreases until it reaches the equilibrium value. The time required to reach equilibrium depends on the diffusion rate and adsorption rate of the surfactant.

[0229] One method for measuring dynamic surface tension is using a maximum bubble pressure tenometer. This device measures the maximum internal pressure of a bubble formed in a liquid using a capillary. The measured value corresponds to the surface tension at a specific surface elapsed time, which is the time from the start of bubble formation until the maximum pressure is reached. The dependence of surface tension on surface elapsed time can be measured by varying the rate at which bubbles are formed.

[0230] Surface-active compounds can also be evaluated by their wetting ability on solid substrates, measured by the contact angle. When a droplet comes into contact with a solid surface in a third medium such as air, a three-phase line is formed between the liquid, gas, and solid. The contact angle is the angle between the surface and the unit vector of surface tension, which is tangent to the droplet and plays a role in the three-phase line. The contact angle (also known as the wetting angle) is a measure of how well a liquid wets a solid. In the case of complete wetting, the liquid is completely spread over the solid, and the contact angle is 0°. Wetting properties are typically measured at concentrations of 1–10 × CMC for any given compound, but they are not concentration-dependent. Therefore, wetting property measurements may be taken at higher or lower concentrations.

[0231] One method involves using an optical contact angle goniometer to measure the contact angle. This device uses a digital camera and software to analyze the contour shape of a stationary liquid droplet on a surface to determine the contact angle.

[0232] Possible applications of the surface-active compounds of this disclosure include formulations for use in shampoos, hair conditioners, detergents, spot-free rinse solutions, floor and carpet cleaners, graffiti removers, crop protection wetting agents, crop protection auxiliaries, and aerosol spray coatings.

[0233] Those skilled in the art will understand that even slight differences between compounds can lead to significantly different surfactant properties, and therefore, different compounds may be used with different substrates in different applications. Those skilled in the art will further understand that surfactant properties are not always predictable based on chemical structure, as will be further demonstrated below. For example, surfactant 9 and the comparative surfactant, differing only in the number of methylene groups in R3, exhibit different surfactant properties. Surprisingly, surfactant 9 exhibits excellent activity, as will be further discussed below, while the comparative surfactant exhibits inferior surfactant properties.

[0234] The following, non-limiting embodiments are provided to illustrate the different properties of different surfactants. Table 1 below shows the abbreviations of surfactants and their corresponding chemical structures.

[0235] [Table 1-1]

[0236] [Table 1-2]

[0237] [Table 1-3]

[0238] These compounds may be effective in any of the formulations intended in this disclosure as wetting or foaming agents, dispersants, emulsifiers, and surfactants useful for detergents. The amount of the compound disclosed herein used in the formulation may be as low as about 0.001% by weight, about 0.05% by weight, about 0.1% by weight, about 0.5% by weight, about 1% by weight, about 2% by weight, or about 5% by weight, or as high as about 8% by weight, about 10% by weight, about 15% by weight, about 20% by weight, or about 25% by weight, about 30% by weight, about 40% by weight, about 50% by weight, or about 80% by weight, or within any range of 0.001% to 80% by weight, or 0.05% to 50% by weight, or 0.1% to 20% by weight, or 0.5% to 10% by weight, or 1% to 8% by weight, or 2% to 8% by weight, or 5% to 8% by weight, or within any range using any two of the above values.

[0239] Table 2 includes comparative surfactants, including their names and structures.

[0240] [Table 2]

[0241] The surfactants useful in the formulations disclosed herein may have a critical micelle concentration (CMC) of 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 any CMC that falls within the range encompassed by the above endpoints. For example, a surfactant may have a CMC of about 0.01 to about 15 mmol, about 0.05 to about 10 mmol, or about 0.1 to about 5 mmol.

[0242] Surfactants useful in the formulations disclosed herein may have minimum surface tension plateau values ​​of 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 any minimum surface tension plateau value that falls within the range encompassed by the above endpoints. For example, a surfactant may have a minimum surface tension plateau value of about 15 to about 25 mN / m, about 18 to about 22 mN / m, or about 20 to about 21 mN / m.

[0243] Surfactants with antibacterial activity Cells are the fundamental units of all living organisms, and every cell possesses a set of individual organelles, each responsible for performing various types of functions and storing genetic information for the development and function of the organism. The outer boundary of the cell is called the cell membrane, which acts as a barrier and controls the transport of substances between the inside and outside of the cell. The cell membrane can be destroyed by a process called lysis, resulting in cell death, which is fundamentally the basis of all antimicrobial processes. In situations where this function cannot be introduced by other means for economic reasons, the use of surfactants with intrinsic biocidal activity in paints, adhesives, and inks, as well as in various other applications, can be extremely important.

[0244] Traditionally, cationic surfactants have been used as antimicrobial agents in industrial sectors such as the food industry and hospitals. Unlike conventional antimicrobial chemicals that rely on a "lock-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)). To function as a good antimicrobial agent, surfactants need to effectively kill bacteria or other unwanted pathogenic microorganisms without disrupting mammalian cells. Today, with increasing awareness of the potential cytotoxicity and environmental hazards caused by certain chemicals, there has also been a collaborative effort to develop surfactants that reduce concerns about cytotoxicity that may arise from the lack of selectivity of conventional quaternary ammonium surfactants, which are known to indiscriminately disrupt biological membranes regardless of cell type.

[0245] The surfactants of this disclosure are shown in a standard protocol for evaluating antimicrobial activity, known as the minimum inhibitory concentration (MIC) test. The following table shows the MIC results for examples of the surfactants of this disclosure.

[0246] [Table 3] [Examples]

[0247] Nuclear magnetic resonance (NMR) spectroscopy was performed using a Bruker 500 MHz spectrometer. The critical micelle concentration (CMC) was determined at 23°C using a Wilhelmie plate method with a tensile strength meter (DCAT 11, DataPhysics Instruments GmbH) equipped with a Pt-Ir plate. Dynamic surface tension was determined at 23°C using a maximum bubble pressure tensile strength meter (Kruss BP100, Kruss GmbH). The contact angle was determined using an optical contact angle goniometer (OCA 15 Pro, DataPhysics GmbH) equipped with a digital camera.

[0248] Example 1: Synthesis of 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)hexanamide 6-(dimethylamino)hexanoic acid (2.00 g, 12.56 mmol, 1 equivalent) was dissolved in toluene (50 mL) in a 100 mL round-bottom boiling flask equipped with a Dean Stark trap, followed by the addition of 3-aminopropyltris(trimethylsiloxy)silane (5.48 mL, 13.81 mmol, 1.1 equivalents). The reaction vessel was heated, and the reaction mixture was refluxed for 24 hours until no more water separated into the Dean Stark tube. The solvent was removed by vacuum to obtain 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).

[0249] 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-oxohexane-1-aminium bromide (surfactant 1)

[0250] [ka]

[0251] 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 at 70°C for 12 hours. The solvent was removed by 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).

[0252] Example 2b: Identification of the physical properties of surfactant 1 The critical micelle concentration (CMC) of surfactant 1 was measured. From the surface tension, which changes with concentration in water, the CMC was identified as approximately 9.883 mmol at pH 8. The minimum surface tension plateau value achievable with this surfactant was approximately 20.67 mN / m, indicating that this surfactant possesses significant surface activity. These results are plotted in Figure 1 as surface tension versus concentration.

[0253] 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-oxohexane-1-aminium bromide (surfactant 2)

[0254] [ka]

[0255] The siloxane derivative described in Example 1 (1 g, 2.02 mmol) was dissolved in DMF (15 mL), and ethyl bromoethyl (0.25 mL, 2.4 mmol) was added. The mixture was stirred at 70°C for 12 hours. The solvent was removed by vacuum, and the crude product was washed twice with hexane to obtain surfactant 2 as a brown liquid (900 mg).

[0256] Example 3b: Identification of the physical properties of surfactant 2 The critical micelle concentration (CMC) of surfactant 2 was measured. From the surface tension, which changes with concentration in water, the CMC was determined to be approximately 0.2171 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.36 mN / m, indicating that this surfactant possesses significant surface activity. These results are plotted as surface tension versus concentration in Figure 2.

[0257] 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-oxohexane-1-aminium iodide (surfactant 3)

[0258] [ka]

[0259] 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 iodide (674 mg). The reaction mixture was refluxed at 40°C for 14 hours. The residual sodium carbonate was removed by filtration, and the filtrate was concentrated. The crude product was washed twice with hexane to remove excess allyl iodide, and surfactant 3 was obtained as a brown liquid (850 mg).

[0260] Example 4b: Identification of the physical properties of surfactant 3 The critical micelle concentration (CMC) of surfactant 3 was measured. From the surface tension, which changes with concentration in water, the CMC was determined to be approximately 1.3599 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.67 mN / m, indicating that this surfactant possesses significant surface activity. These results are plotted as surface tension versus concentration in Figure 3.

[0261] 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-(propa-2-in-1-yl)hexane-1-aminium bromide (surfactant 4)

[0262] [ka]

[0263] The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL). Propargyl bromide (674 mg, 2.4 mmol) was added, and the mixture was stirred at 70°C for 12 hours. The solvent was removed by vacuum, and the crude product was washed twice with hexane to obtain surfactant 4 as a brown liquid (850 mg).

[0264] Example 5b: Identification of the physical properties of surfactant 4 The critical micelle concentration (CMC) of surfactant 4 was measured. From the surface tension, which changes with concentration in water, the CMC was determined to be approximately 0.2419 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.54 mN / m, indicating that this surfactant possesses significant surface activity. These results are plotted as surface tension versus concentration in Figure 4.

[0265] 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-oxohexane-1-aminium bromide (surfactant 5)

[0266] [ka]

[0267] 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 by vacuum, and the crude product was washed twice with hexane to obtain surfactant 5 as a brown liquid (800 mg).

[0268] Example 6b: Identification of the physical properties of surfactant 5 The critical micelle concentration (CMC) of surfactant 5 was measured. From the surface tension, which changes with concentration in water, the CMC was determined to be approximately 0.4622 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.40 mN / m, indicating that this surfactant possesses significant surface activity. These results are plotted as surface tension versus concentration in Figure 5.

[0269] 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-oxohexane-1-aminium bromide (surfactant 6)

[0270] [ka]

[0271] 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 by vacuum, and the crude product was washed twice with hexane to obtain surfactant 6 as a brown liquid (900 mg).

[0272] Example 7b: Identification of the physical properties of surfactant 6 The critical micelle concentration (CMC) of surfactant 6 was measured. From the surface tension, which changes with concentration in water, the CMC was determined to be approximately 0.3989 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.48 mN / m, indicating that this surfactant possesses significant surface activity. These results are plotted as surface tension versus concentration in Figure 6.

[0273] 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-oxohexane-1-aminium iodide (surfactant 7)

[0274] [ka]

[0275] 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. The residual base was removed by filtration, and the filtrate was concentrated. The crude product was washed twice with hexane to remove excess iodopropanol, and surfactant 7 was obtained as a brown liquid (780 mg).

[0276] Example 8b: Identification of the physical properties of surfactant 7 The critical micelle concentration (CMC) of surfactant 7 was measured. From the surface tension, which changes with concentration in water, the CMC was determined to be approximately 0.4568 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.61 mN / m, indicating that this surfactant possesses significant surface activity. These results are plotted as surface tension versus concentration in Figure 7.

[0277] 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-oxohexane-1-aminium iodide (surfactant 8)

[0278] [ka]

[0279] The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) 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 obtain surfactant 8 (910 mg).

[0280] Example 9b: Identification of the physical properties of surfactant 8 The critical micelle concentration (CMC) of surfactant 8 was measured. From the surface tension, which changes with concentration in water, the CMC was determined to be approximately 0.9986 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.41 mN / m, indicating that this surfactant possesses significant surface activity. These results are plotted as surface tension versus concentration in Figure 8.

[0281] 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-diaminium dibromide (surfactant 10)

[0282] [ka]

[0283] 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 as a brown liquid (900 mg).

[0284] Example 10b: Identification of the physical properties of surfactant 10 The critical micelle concentration (CMC) of surfactant 10 was measured. From the surface tension, which changes with concentration in water, the CMC was determined to be approximately 0.0631 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 22.12 mN / m, indicating that this surfactant possesses surface activity. These results are plotted in Figure 10 as surface tension versus concentration.

[0285] 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-oxohexane-1-aminium bromide (surfactant 9)

[0286] [ka]

[0287] 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 by vacuum. The crude product was washed twice with hexane to obtain N-(5-carboxypentyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexane-1-aminium bromide as a viscous brown liquid (650 mg).

[0288] Example 11b: Identification of the physical properties of surfactant 9 The critical micelle concentration (CMC) of surfactant 9a was measured. From the surface tension, which changes with concentration in water, the CMC was determined to be approximately 0.2237 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.52 mN / m, indicating that this surfactant possesses excellent surface activity. These results are plotted as surface tension versus concentration in Figure 9.

[0289] 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-oxohexane-1-aminium bromide (comparative surfactant)

[0290] [ka]

[0291] 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 obtain surfactant 9b as a brown liquid (700 mg).

[0292] Comparative Example A2: Identification of the physical properties of the comparative surfactant. The critical micelle concentration (CMC) of surfactant 9b was measured. From the surface tension, which changed with concentration in water, the CMC was determined to be approximately 17.28 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 29.16 mN / m. These results are plotted as surface tension versus concentration in Figure 11. This result demonstrates the difficulty of predicting surfactant activity based on chemical structure, and shows that surfactant 9, which differs only in the number of methylene groups in the carboxylic acid, exhibits remarkably superior activity.

[0293] 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-oxohexane-1-aminium bromide (surfactant 11)

[0294] [ka]

[0295] 4-(4-bromobutyl)benzoic acid is added to the siloxane derivative described in Example 1 to obtain 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-oxohexane-1-aminium bromide.

[0296] 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-oxohexane-1-aminium bromide (surfactant 12)

[0297] [ka]

[0298] 4-(bromomethyl)benzoic acid is added to the siloxane derivative described in Example 1 to obtain N-(4-carboxybenzyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexane-1-aminium bromide.

[0299] Example 14: Formulations for ink fixing solutions This example provides a formulation of an ink fixing solution. The components of the formulation are shown in Table 3 below.

[0300] [Table 4]

[0301] Example 15: Formulations for paints This embodiment provides a formulation for use as a paint. The formulation is shown in Table 4 below.

[0302] [Table 5]

[0303] Example 16: Formulations for adhesives This embodiment provides a formulation for use as an adhesive. The formulation is shown in Table 5 below.

[0304] [Table 6]

[0305] Example 17: Formulations for paint strippers This embodiment provides a formulation for use as an insecticide. The formulation is shown in Table 6 below.

[0306] [Table 7]

[0307] Example 18: Antimicrobial MIC test The antimicrobial activity of surfactants was investigated using known methods and standard protocols, as well as various types of microorganisms. More specifically, a minimum inhibitory concentration (MIC) test protocol using serial dilution was applied to obtain concentration-dependent microbial growth inhibition measurements for Gram-positive bacteria (e.g., the anaerobic Streptococcus mutans, and Staphylococcus aureus, which is normally aerobic but can also grow anaerobically) and Gram-negative bacteria (e.g., the anaerobic Escherichia coli, or the aerobic Pseudomonas aeruginosa).

[0308] Bacteria were grown overnight in a suitable growth medium, which was tryptic soy broth. Before testing, the concentration of the test organisms was confirmed using a spectrophotometer capable of measuring optical density. Next, these bacterial samples were diluted to approximately 1E3–1E4 CFU / mL. Then, 10 mL of the bacterial culture thus prepared was inoculated into the test wells of a 96-well plate, each containing a suitable growth medium, which was tryptic soy agar. After inoculation of the bacterial culture, these wells were treated with the test sample, serially diluted, and incubated at a temperature of 37±1°C and a relative humidity of 90% or higher for approximately 24±1 hours.

[0309] The test surfactant was prepared into serial dilutions. All dilutions were performed stepwise in 96-well microtiter plates using a multichannel pipette. The serial dilutions were pre-established by range-finding exercises to determine the upper limit of high concentrations and the range of diluted low concentrations, ensuring that the test substance would not completely inhibit bacterial growth but would still be effective.

[0310] Next, the approximate concentration of the test surfactant that inhibited bacterial growth was determined using an MIC (Micro-Insulator). In this antimicrobial testing protocol, a reference substance is typically used as a positive control; in this case, ADBAC, a quaternary amine with CAS number 139-08-2, was used as the appropriate test reference substance.

[0311] Test measurements were performed on repeated samples in 96-well plates, and the identified MICs were reported as the mean of the rounded integers. The mean of the repeated sample data was determined by identifying the mean (arithmetic mean) in the selected measurements using the following formula: Arithmetic mean = Sum of the values ​​in the set / Number of samples. Subsequently, the variability of the measurements was reported in the form of MIC ± based on the identified mean.

[0312] manner Embodiment 1 is a formulation for an ink fixing solution, which is, At least one surfactant of formula I,

[0313] [ka]

[0314] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. It includes a fixative and water.

[0315] Embodiment 2 is the formulation according to Embodiment 1, wherein the fixing agent is a metal carboxylate salt. Embodiment 3 is the formulation according to either Embodiment 1 or Embodiment 2, further comprising a desiccant. Embodiment 4 is a formulation according to any one of Embodiments 1 to 3, further comprising an acid.

[0316] Embodiment 5 is a formulation according to any one of Embodiments 1 to 4, further comprising an aqueous vehicle. Embodiment 6 is a formulation according to any one of Embodiments 1 to 5, further comprising a coloring agent dispersed in an aqueous vehicle.

[0317] Embodiment 7 is a formulation for paint, which comprises at least one surfactant of formula I,

[0318] [ka]

[0319] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. latex, It also includes water.

[0320] Embodiment 8 is the formulation according to Embodiment 7, further comprising one or more dryers. Embodiment 9 is a formulation according to either Embodiment 7 or Embodiment 8, further comprising one or more solvents.

[0321] Embodiment 10 is a formulation according to any one of Embodiments 7 to 9, further comprising one or more pigments. Embodiment 11 is a formulation for paint, which comprises at least one surfactant of formula I,

[0322] [ka]

[0323] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. binder It also includes water.

[0324] Embodiment 12 is the formulation according to Embodiment 11, further comprising one or more dryers. Embodiment 13 is a formulation according to either Embodiment 11 or Embodiment 12, further comprising one or more solvents.

[0325] Embodiment 14 is a formulation according to any one of Embodiments 11 to 13, further comprising one or more pigments. Embodiment 15 is a formulation for paint, which comprises at least one surfactant of formula I,

[0326] [ka]

[0327] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. glue, It also includes water.

[0328] Embodiment 16 is the formulation according to Embodiment 15, further comprising a filler. Embodiment 17 is a formulation for a paint stripper, which comprises at least one surfactant of formula I,

[0329] [ka]

[0330] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. 1,2-Dichloroethylene, It also includes water.

[0331] Embodiment 18 is the formulation according to Embodiment 17, further comprising wax. Embodiment 19 is a formulation according to either Embodiment 17 or Embodiment 18, further comprising a corrosion inhibitor.

[0332] Embodiment 20 is a formulation according to any one of Embodiments 17 to 19, further comprising an organic solvent. Embodiment 21 is a formulation according to any one of Embodiments 17 to 20, further comprising a thickening agent.

[0333] Embodiment 22 is a formulation for a paint stripper, which comprises at least one surfactant of formula I,

[0334] [ka]

[0335] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. 1,2-Dichloroethylene, One or more cosolvents, It also includes water.

[0336] Embodiment 23 is the formulation according to Embodiment 22, wherein one or more cosolvents are selected from aromatic alcohols, aromatic ethers, and aliphatic alcohols. Embodiment 24 is the formulation according to either Embodiment 22 or Embodiment 23, further comprising wax.

[0337] Embodiment 25 is a formulation according to any one of Embodiments 22 to 24, further comprising a corrosion inhibitor. Embodiment 26 is a formulation according to any one of Embodiments 22 to 25, further comprising an organic solvent.

[0338] Embodiment 27 is a formulation according to any one of Embodiments 22 to 26, further comprising a thickening agent. Embodiment 28 is the use of the compound of formula I as a surfactant in an ink fixing agent formulation.

[0339] [ka]

[0340] In the formula, R 1 and R 2It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is selected from the group consisting of chlorides, bromides, and iodides. The formulation comprises at least one surfactant of formula I, a fixative, and water.

[0341] Embodiment 29 is the use described in Embodiment 1, wherein the fixing agent is a metal carboxylate salt. Embodiment 30 is the use according to either Embodiment 28 or Embodiment 29, further comprising a desiccant.

[0342] Embodiment 31 is the use described in any one of Embodiments 28 to 30, further comprising an acid. Embodiment 32 is the use according to any one of Embodiments 28 to 31, further comprising an aqueous vehicle.

[0343] Embodiment 33 is the use according to any one of Embodiments 28 to 32, further comprising a colorant dispersed in an aqueous vehicle. Embodiment 34 is the use of a compound of formula I as a surfactant in a paint formulation,

[0344] [ka]

[0345] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is selected from the group consisting of chlorides, bromides, and iodides. The formulation comprises at least one surfactant of formula I, latex, and water.

[0346] Embodiment 35 is the use described in Embodiment 34, further comprising one or more dryers. Embodiment 36 is the use according to either Embodiment 34 or Embodiment 35, further comprising one or more solvents.

[0347] Embodiment 37 is a use according to any one of Embodiments 34 to 36, further comprising one or more pigments. Embodiment 38 is the use of a compound of formula I as a surfactant in a paint formulation.

[0348] [ka]

[0349] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is selected from the group consisting of chlorides, bromides, and iodides. The formulation comprises at least one surfactant of formula I, a binder, and water.

[0350] Embodiment 39 is the formulation according to Embodiment 38, further comprising one or more dryers. Embodiment 40 is a formulation according to either Embodiment 38 or Embodiment 39, further comprising one or more solvents.

[0351] Embodiment 41 is a formulation according to any one of Embodiments 38 to 40, further comprising one or more pigments. Embodiment 42 is the use of compound I as a surfactant in an adhesive formulation,

[0352] [ka]

[0353] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is selected from the group consisting of chlorides, bromides, and iodides. The formulation comprises at least one surfactant of formula I, an adhesive, and water.

[0354] Embodiment 43 is the use described in Embodiment 42, further comprising a filler. Embodiment 44 is the use of the compound of formula I as a surfactant in a paint stripper formulation.

[0355] [ka]

[0356] In the formula, R 1 and R 2It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is selected from the group consisting of chlorides, bromides, and iodides. The formulation comprises at least one surfactant of formula I, 1,2-dichloroethylene, and water.

[0357] Embodiment 45 is the use described in Embodiment 44, further comprising wax. Embodiment 46 is the use according to either Embodiment 44 or Embodiment 45, further comprising a corrosion inhibitor.

[0358] Embodiment 47 is the use according to any one of Embodiments 44 to 46, further comprising an organic solvent. Embodiment 48 is the use according to any one of Embodiments 44 to 47, further comprising a thickening agent.

[0359] Embodiment 49 is the use of the compound of formula I as a surfactant in a paint stripper formulation.

[0360] [ka]

[0361] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is selected from the group consisting of chlorides, bromides, and iodides. The formulation further comprises 1,2-dichloroethylene, one or more cosolvents, and water.

[0362] Embodiment 50 is the use described in Embodiment 49, wherein one or more cosolvents are selected from aromatic alcohols, aromatic ethers, and aliphatic alcohols. Embodiment 51 is the use according to either Embodiment 49 or Embodiment 50, further comprising wax.

[0363] Embodiment 52 is the use according to any one of Embodiments 49 to 51, further comprising a corrosion inhibitor. Embodiment 53 is the use according to any one of Embodiments 49 to 52, further comprising an organic solvent.

[0364] Embodiment 54 is the use according to any one of Embodiments 48 to 53, further comprising a thickening agent. Embodiment 55 is a formulation of an ink, paint, adhesive, or paint remover disclosed in any one of Embodiments 1 to 27.

[0365] Embodiment 56 is a surfactant of at least one compound of formula (I),

[0366] [ka]

[0367] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, alkylphosphonates, C3-C8 carboxylic acids, and C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is identical or different from the first molecule of formula I; n is an integer from 1 to 12; and X is selected from the group consisting of chlorides, bromides, and iodides. It is used as a formulation of inks, paints, adhesives, or paint removers containing surfactants.

[0368] Embodiment 57 is a method for manufacturing the preparation described in any one of Embodiments 1 to 6, which is: The synthesis of the compound of formula I,

[0369] [ka]

[0370] In the formula, R 1 and R 2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, C3-C8 carboxylic acids, and C1-C2 carboxylic acids. 10 The synthesis comprises a ring-opening step of opening a lactam ring to obtain an amino acid having an N-terminus and a C-terminus, a first alkylation step of alkyl benzoic acid and a C1-C6 linker bonded 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 the group consisting of chlorides, bromides, and iodides, and the method comprises a ring-opening step of opening a lactam ring to obtain an amino acid having an N-terminus and a C-terminus; a first alkylation step of alkylating the N-terminus to obtain a tertiary amine; a coupling step of reacting the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to obtain a siloxane derivative; and a second alkylation step of alkylating the N-terminus to obtain a quaternary amine of formula I. This includes adding a fixative and water.

[0371] Embodiment 58 is a method for manufacturing the preparation described in any one of Embodiments 7 to 14, which is: The synthesis of the compound of formula I,

[0372] [ka]

[0373] In the formula, R 1 and R2 It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, C3-C8 carboxylic acids, and C1-C2 carboxylic acids. 10 The synthesis comprises a ring-opening step of opening a lactam ring to obtain an amino acid having an N-terminus and a C-terminus, a first alkylation step of alkyl benzoic acid and a C1-C6 linker bonded 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 the group consisting of chlorides, bromides, and iodides, and the method comprises a ring-opening step of opening a lactam ring to obtain an amino acid having an N-terminus and a C-terminus; a first alkylation step of alkylating the N-terminus to obtain a tertiary amine; a coupling step of reacting the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to obtain a siloxane derivative; and a second alkylation step of alkylating the N-terminus to obtain a quaternary amine of formula I. This includes adding latex or a binder and water.

[0374] Embodiment 59 is a method for manufacturing the preparation described in any one of Embodiments 15 to 16, which is: The synthesis of the compound of formula I,

[0375] [ka]

[0376] In the formula, R 1 and R 2It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, C3-C8 carboxylic acids, and C1-C2 carboxylic acids. 10 The synthesis comprises a ring-opening step of opening a lactam ring to obtain an amino acid having an N-terminus and a C-terminus, a first alkylation step of alkyl benzoic acid and a C1-C6 linker bonded 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 the group consisting of chlorides, bromides, and iodides, and the method comprises a ring-opening step of opening a lactam ring to obtain an amino acid having an N-terminus and a C-terminus; a first alkylation step of alkylating the N-terminus to obtain a tertiary amine; a coupling step of reacting the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to obtain a siloxane derivative; and a second alkylation step of alkylating the N-terminus to obtain a quaternary amine of formula I. This includes adding adhesive and water.

[0377] Embodiment 60 is a method for manufacturing a pharmaceutical product as described in any one of Embodiments 17 to 27, which is: The synthesis of the compound of formula I,

[0378] [ka]

[0379] In the formula, R 1 and R 2It comprises at least one group selected from the group consisting of C1-C6 alkyls, which may be identical or different, and optionally the C1-C6 alkyl may include one or more oxygen, nitrogen, or sulfur atoms, or at least one of these atoms, and optionally the alkyl chain may be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;R 3 These include alkenyls, alkynyls, esters, alcohols, arylalkyls, alkoxyalkyl ethers, alkyl phosphates, C3-C8 carboxylic acids, and C1-C2 carboxylic acids. 10 The synthesis comprises a ring-opening step of opening a lactam ring to obtain an amino acid having an N-terminus and a C-terminus, a first alkylation step of alkyl benzoic acid and a C1-C6 linker bonded 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 the group consisting of chlorides, bromides, and iodides, and the method comprises a ring-opening step of opening a lactam ring to obtain an amino acid having an N-terminus and a C-terminus; a first alkylation step of alkylating the N-terminus to obtain a tertiary amine; a coupling step of reacting the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to obtain a siloxane derivative; and a second alkylation step of alkylating the N-terminus to obtain a quaternary amine of formula I. This includes adding 1,2-dichloroethylene, optionally one or more cosolvents, and water.

[0380] Embodiment 61 is the method according to any one of Embodiments 57 to 60, wherein the lactam is caprolactam. Embodiment 62 is a method according to any one of Embodiments 57 to 61, wherein in the first alkylation step, the tertiary amine is 6-(dimethylamino)hexanoic acid.

[0381] Embodiment 63 is a method according to any one of Embodiments 57 to 62, wherein in the second alkylation step, the N-terminus is alkylated with an alkylating agent selected from the group consisting of benzyl bromide, ethyl bromo, 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 ink fixing solution: At least one surfactant of formula I, 【Chemistry 1】 In the formula, R １ and R ２ are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally the C １ ~C ６ The alkyl group may contain one or more atoms from among oxygen, nitrogen, or sulfur, or at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ is selected from the group consisting of alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ to C ８ carboxylic acid, C １ to C １０ alkylbenzoic acid, and a C １ to C ６ linker attached to the second molecule of formula I, and the second molecules are the same or different; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. Fixative, and water, A formulation containing the above.

2. The formulation according to claim 1, wherein the fixing agent comprises a metal carboxylate salt.

3. The formulation according to claim 1 or claim 2, further comprising a hygroscopic agent, an acid, an aqueous vehicle, or a coloring agent dispersed in an aqueous vehicle.

4. A formulation for paints: At least one surfactant of formula I, 【Chemistry 2】 In the formula, R １ and R ２ are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally the C １ ~C ６ The alkyl group may contain one or more atoms from among oxygen, nitrogen, or sulfur, or at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ ~C ８ Carboxylic acid, C １ ~C １０ Alkylbenzoic acid, and C bonded to the second molecule of formula I １ ~C ６ Selected from the group consisting of linkers, the second molecule is the same or different; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. Latex or binder, and water, A formulation containing the above.

5. The formulation according to claim 4, further comprising one or more dryers, one or more solvents, or one or more pigments.

6. A formulation for adhesives: At least one surfactant of formula I, 【Transformation 3】 In the formula, R １ and R ２ are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally the C １ ~C ６ The alkyl group may contain one or more atoms from among oxygen, nitrogen, or sulfur, or at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ ~C ８ Carboxylic acid, C １ ~C １０ Alkylbenzoic acid, and C bonded to the second molecule of formula I １ ~C ６ Selected from the group consisting of linkers, the second molecule is the same or different; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. Adhesives, and water, A formulation containing the above.

7. The formulation according to claim 6, further comprising a filler.

8. A formulation for paint strippers: At least one surfactant of formula I, 【Chemistry 4】 In the formula, R １ and R ２ are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally the C １ ~C ６ The alkyl group may contain one or more atoms from among oxygen, nitrogen, or sulfur, or at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ ~C ８ Carboxylic acid, C １ ~C １０ Alkylbenzoic acid, and C bonded to the second molecule of formula I １ ~C ６ Selected from the group consisting of linkers, the second molecule is the same or different; n is an integer from 1 to 12; and X is a surfactant selected from the group consisting of chlorides, bromides, and iodides. 1,2-dichloroethylene, optionally one or more cosolvents selected from aromatic alcohols, aromatic ethers, and aliphatic alcohols, and water, A formulation containing the above.

9. The formulation according to claim 8, further comprising a wax, a corrosion inhibitor, an organic solvent, or a thickener.

10. A method for producing a pharmaceutical product according to any one of claims 1 to 9: The synthesis of the compound of formula I, 【Transformation 5】 In the formula, R １ and R ２ are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally the C １ ~C ６ The alkyl group may contain one or more atoms from among oxygen, nitrogen, or sulfur, or at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ ~C ８ Carboxylic acid, C １ ~C １０ Alkylbenzoic acid, and C bonded to the second molecule of formula I １ ~C ６ Selected from the group consisting of linkers, the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from the group consisting of chlorides, bromides, and iodides, and the method is A ring-opening step to open the lactam ring and obtain an amino acid having an N-terminus and a C-terminus, A first alkylation step is performed to alkylate the N-terminus to obtain a tertiary amine, A coupling step to obtain a siloxane derivative by reacting the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane, The synthesis includes a second alkylation step of alkylating the N-terminus to obtain a quaternary amine of formula I, Adding a fixative, latex, binder, adhesive, 1,2-dichloroethylene, or at least one of one or more cosolvents, and water. Methods that include...

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

12. Use of the formulation according to any one of claims 1 to 3 as an ink fixing solution.

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

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

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

Images