Treated article, method for producing the treated article, and dispersant for use in producing the treated article

Abstract

The treated articles include fibers, sizing agents, and retention aids. The sizing agents include waxes or components thereof having an acid number of 10 mg to 220 mg KOH / g as measured in accordance with USP 401. The retention aids include nitrogen-containing polymers independently selected from the group consisting of (i) a nitrogen-containing polymer of Formula I, (ii) polyethyleneimine, (iii) a polyaminoamide, (iv) a copolymer formed from the reaction product of epichlorohydrin and dimethylamine, and (v) combinations thereof.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to and all benefits of U.S. Provisional Patent Application No. 63 / 212,776, filed June 21, 2020, and U.S. Provisional Patent Application No. 63 / 121,500, filed December 4, 2021, the disclosures of which are incorporated herein by reference in their entireties.

[0002] Technical Field FIELD OF THE DISCLOSURE

[0002] The following disclosure relates to treated articles, methods of making the treated articles, and dispersants for use in making the treated articles. [Background technology]

[0003]

[0003] High-performance treatment articles (e.g., paper products) typically derive their performance from the inclusion of fluoropolymers. The recent global trend toward reducing the fluorine content in treated articles, particularly those used in the food industry, has resulted in articles that are considered more environmentally friendly. However, these environmentally friendly articles typically lack certain performance characteristics compared to their fluorine-containing counterparts. Therefore, there remains a need for the development of high-performance, improved treatment articles, or dispersants for making improved treatment articles. Summary of the Invention

[0004] The present disclosure provides treated articles. The treated articles include fibers, sizing agents, and retention aids. The sizing agents include waxes or components thereof having an acid number of 10 mg to 220 mg KOH / g as measured in accordance with USP 401. The retention aids include nitrogen-containing polymers independently selected from the group consisting of (i) a nitrogen-containing polymer of Formula I, (ii) polyethyleneimine, (iii) a polyaminoamide, (iv) a copolymer formed from the reaction product of epichlorohydrin and dimethylamine, and (v) combinations thereof.

[0005] The present disclosure also provides dispersants, including solvents, sizing agents, and retention aids, for use in manufacturing treated articles.

[0006] The treated articles are typically fluorine-free and have an excellent balance of performance properties, specifically, the synergistic combination of sizing and retention aids results in treated articles with excellent corn oil bleed-through prevention / resistance and hot water repellency. DETAILED DESCRIPTION OF THE INVENTION

[0005]

[0007] The present disclosure provides a dispersant for use in making treated articles. The dispersant includes three main components: a solvent, a sizing agent, and a retention aid.

[0008] First, referring to the solvent, the solvent may include various solvating liquids or may include a single liquid. The solvent generally includes at least water. Optionally, the solvent may include other liquids, which are liquids miscible with water. Specific examples of water-miscible solvents include at least one solvent selected from the group consisting of propylene glycol, dipropylene glycol, tripropylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoether ether, tripropylene glycol monomethyl ether, diacetone alcohol, and combinations thereof. Most typically, the solvent includes water or a combination of water and at least one water-miscible solvent selected from the group consisting of propylene glycol, dipropylene glycol, and tripropylene glycol.

[0006]

[0009] The dispersant generally contains the solvent in an amount of at least 40 parts by weight per 100 parts by weight of the dispersant. Alternatively, the dispersant may contain the solvent in an amount of 40 to 90, 50 to 90, 60 to 90, 70 to 90, 80 to 90, 50 to 80, 60 to 80, or about 70 parts by weight per 100 parts by weight of the dispersant. For example, the solvent can contain water (e.g., tap water) and dipropylene glycol, with the water being present in an amount of 50 to 75 parts by weight and the dipropylene glycol being present in an amount of 15 to 40 parts by weight per 100 parts by weight of the dispersant.

[0007]

[0010] When referring to a sizing agent herein, the sizing agent includes a wax or a component thereof. Those skilled in the art will understand that many waxes, particularly natural waxes, include a combination of individual components. For example, naturally occurring beeswax includes palmitate, palmitoleate, and oleate esters of long-chain (e.g., 30-32 carbon) fatty alcohols, each individual component being a "component thereof" with respect to beeswax. For ease of reference, the terms "wax or a component thereof" will be collectively referred to as "wax" throughout the following description.

[0008]

[0011] The wax of the sizing agent has an acid number of 10 mg to 220 mg (KOH / g) as measured in accordance with USP 401. Alternatively, the acid number of the wax may be 10 to 200, 10 to 180, 10 to 160, 10 to 140, 10 to 120, 10 to 100, 10 to 80, 10 to 60, or 10 to 50 mg KOH / g. Alternatively, the acid number of the wax may be 20 to 100, 20 to 80, 20 to 60, 25 to 45, or 150 to 220 KOH / g. For purposes of this disclosure, any reference to the acid number of the wax refers to the acid number as measured in accordance with USP 401.

[0012] The wax is not limited to any particular wax, but when the wax has an acid value of 10 mg to 220 mg (KOH / g), the wax is typically selected from the group consisting of stearates, beeswax (both synthetic and natural), candelilla wax, palmitates, behenates, and combinations thereof. For example, the wax of the sizing agent may be beeswax or stearate, or both. Alternatively, the wax may be behenate or palmitate, or both.

[0013] The wax is generally present in the dispersant in an amount of 10 to 50 parts by weight per 100 parts by weight of dispersant. Alternatively, the wax may be present in an amount of 10 to 45, 10 to 40, 10 to 35, 15 to 50, 20 to 50, or 25 to 50 parts by weight per 100 parts by weight of dispersant.

[0014] Those skilled in the art will appreciate that sizing agents comprising waxes are useful in the process of making treated articles because, as described in more detail below, the sizing agent can be fixed, held, anchored, incorporated, and oriented in or by the fibers within the treated article. As described in more detail below, the sizing agent can be referred to as an internal sizing agent, an external sizing agent, or both, depending on the particular method of incorporating the dispersion into the process of making the treated article.

[0009]

[0015] Referring now to retention aids, the retention aid comprises a nitrogen-containing polymer selected from the group consisting of (i) a nitrogen-containing polymer of Formula I, (ii) polyethyleneimine, (iii) a polyaminoamide, (iv) a copolymer formed from the reaction product of epichlorohydrin and dimethylamine, and (v) combinations thereof.

[0010]

[0016] Formula I below:

[0011] [ka] Formula I The nitrogen-containing polymer is represented by the formula: In Formula I, (a), (b), (c), (d), and (e) each represent the molar ratio of each repeating unit contained in the nitrogen-containing polymer of Formula I. R0 is independently one of the following: hydrogen,

[0012] [ka] and combinations thereof. Rz is independently selected from H, -CH3, and combinations thereof. Rx is independently selected from H, -OH, -COOH, -COOR1, -OCOR1, -R1, -R3OH, -OR1, -NR1R1, -R3NH2, -NH2, -COO(CH2)2N(R1)2, -COO(CH2)2N + (R1)3X - , -COO(CH2)3N + (R1)3X - and combinations thereof, with the proviso that when Rx is -NH2, Rz is -CH3. Y is independently selected from H, -OH, -R1, -OR1, -NR1R1, -NH2, and combinations thereof. Z is independently selected from H, -OH, -C=O, -R1, -OR1, -NR1R1, -NH2, and combinations thereof. R1 is independently selected from H, linear or branched alkyl or alkenyl containing up to 22 carbons, and combinations thereof. R2 is independently selected from H, monosaccharide, oligosaccharide, polysaccharide moieties, optionally linear or branched alkyl or alkenyl groups of up to 22 carbons containing hydroxyl or aldehyde groups, and combinations thereof. R3 is independently selected from linear or branched alkyl or alkenyl containing up to 22 carbons, or combinations thereof. R4 is independently selected from linear or branched alkyl groups containing up to 18 carbon atoms, optionally substituted with a hydroxyl group, and combinations thereof. R5 is independently selected from H, -OH, -COOH, -COOR1, -OCOR1, -R1, -R1OH, -OR1, -CONH2, - CONHCHOHCHO, —NR1, —NR1R1, —R1NH2, —NH2, and combinations thereof. A is independently selected from C═O, —CH2, and combinations thereof. Finally, X ― are independently anions.

[0013]

[0017] As noted above, in Formula I, (a), (b), (c), (d), and (e) each represent the molar ratio of each repeat unit contained in the nitrogen-containing polymer of Formula I. For ease of reference, a repeat unit having molar ratio (a) will be referred to as repeat unit (a), a repeat unit having molar ratio (b) will be referred to as repeat unit (b), a repeat unit having molar ratio (c) will be referred to as repeat unit (c), a repeat unit having molar ratio (d) will be referred to as repeat unit (d), and a repeat unit having molar ratio (e) will be referred to as repeat unit (e). It should be understood that the structural formulas representing each individual repeat unit also represent multiple separate repeat units. The molar ratio of each repeat unit is the total molar ratio of each separate unit represented by the repeat unit. For example, the nitrogen-containing polymer of formula I may be in an amount of 50 mole % of:

[0014] [ka] The following repeating unit (b) with R0 represented by:

[0015] [ka] and the following in an amount of 50 mol %:

[0016] [ka] The following repeating unit (b) with R0:

[0017] [ka] When the nitrogen-containing polymer comprises repeat units (b) in an amount totaling 100 mole %. It should also be understood that the individual repeat units within the nitrogen-containing polymer of Formula I are randomly distributed.

[0018] The value of each individual molar ratio represented by (a), (b), (c), (d), and (e) can range from 0 to 100 mol%, with the sum of (a), (b), (c), (d), and (e) being 100 mol%. This means that the nitrogen-containing polymer of Formula I does not contain any additional repeating units within its structure. When the molar ratio of (a) is 0, the nitrogen-containing polymer does not contain the repeating unit (a). Conversely, when the molar ratio of (a) is 100, the nitrogen-containing polymer does not contain the repeating units (b), (c), (d), and (e).

[0018]

[0019] wherein the repeating unit (a) is:

[0019] [ka] Referring to the formula (I), the molar ratio of (a) in the repeat unit (a) is typically less than 100 mol %. In other words, typically, when the repeat unit (a) is included in the nitrogen-containing polymer of formula I, the nitrogen-containing polymer includes at least one additional repeat unit. Typically, when the repeat unit (a) is combined with an additional repeat unit, the molar ratio (a) of the repeat unit (a) is less than 30 mol %. However, when the molar ratio (a) of the repeat unit (a) is 100 mol %, Rx can independently be -NR1R1, -R3NH2, -NH2, -COO(CH2)2N(R1)2, -COO(CH2)3N(R1)2, -COO(CH2)2N + (R1)3X - , -COO(CH2)3N + (R1)3X - and combinations thereof. In other words, when the molar ratio of the repeating unit (a) is 100 mol %, Rx is selected so that the repeating unit (a) contains nitrogen.

[0020] wherein the repeating unit (b) is:

[0021] [ka] Referring to the formula (I), the repeat unit (b) may be present in the nitrogen-containing polymer of formula I in a molar ratio of 0 to 100. When the nitrogen-containing polymer contains the repeat unit (b), the repeat unit (b) is typically present in an amount of at least 15 mol %. Alternatively, the repeat unit (b) may be present in an amount of at least 30, 40, 50, 60, 70, 80, or 90 mol %.

[0022] In certain embodiments, R is independently H,

[0023] [ka] and combinations thereof. In other words, in these embodiments, R0 is

[0024] [ka] In other embodiments, R is independently H,

[0025] [ka] and combinations thereof. In still further embodiments, R is independently selected from the group consisting of H,

[0026] [ka] and combinations thereof. Although not required, in each of the embodiments within this paragraph, the combined molar proportion of repeat units (c) and (d) is typically less than 5 mole %. In other words, in these embodiments, the combined molar proportion of repeat units (a), (b), and (e) is at least 95 mole %, typically 100 mole %.

[0027] In certain embodiments, the retention aid is a nitrogen-containing polymer of Formula I, wherein the combined molar proportion of repeat units (c) and (d) is less than 5 mole percent. In other words, in these embodiments, the retention aid is a nitrogen-containing polymer of Formula I, wherein repeat units (a), (b), and (e) collectively represent at least 95 mole percent of the nitrogen-containing polymer. Alternatively, the retention aid is a nitrogen-containing polymer of Formula I, wherein repeat units (a), (b), and (e) collectively represent at least 96, 97, 98, 99, or 100 mole percent. When the retention aid is a nitrogen-containing polymer of Formula I, and repeat units (a), (b), and (e) are present in a total of 100 mole percent, the nitrogen-containing polymer has the following formula II:

[0028] [ka] Formula II It is expressed as:

[0029] In certain embodiments where the retention aid is a nitrogen-containing polymer of Formula II, R is independently H,

[0030] [ka] and combinations thereof. In other embodiments of Formula II, R is independently selected from the group consisting of H,

[0031] [ka] and combinations thereof. In still further embodiments of Formula II, R is independently H,

[0032] [ka] and combinations thereof.

[0033] In certain embodiments where the retention aid is a nitrogen-containing polymer of Formula II, the retention aid is (i) a nitrogen-containing polymer of Formula II, wherein the combined molar proportion of (b) and (e) is 100 mole %, and R is independently H,

[0034] [ka] and combinations thereof; (ii) a nitrogen-containing polymer represented by Formula II, wherein Rx is represented by -RNH, and the molar proportion of (a) is 100 mol %; and (iii) a nitrogen-containing polymer represented by Formula II, wherein the molar proportion of (b) is 100 mol %, and R is independently selected from the group consisting of H,

[0035] [ka] and combinations thereof. In some embodiments, the retention aid comprises (i) a nitrogen-containing polymer of Formula II, wherein the combined molar proportion of (b) and (e) is 100 mole %, and R is independently selected from the group consisting of H,

[0036] [ka] and combinations thereof, wherein the retention aid is selected from the group consisting of Formula IIa:

[0037] [ka] Formula IIa. It may be more narrowly defined as Similarly, in this embodiment, the retention aid comprises (ii) a nitrogen-containing polymer of formula II, where the molar proportion of (a) is 100 mole % and Rx is represented by —R3NH2, the retention aid has the following formula IIb:

[0038] [ka] Formula IIb It may be more narrowly defined as Similarly, in this embodiment, the retention aid comprises (iii) a nitrogen-containing polymer of Formula II, wherein the molar proportion of (b) is 100 mole %, and R is independently H,

[0039] [ka] and combinations thereof, wherein the retention aid is selected from the group consisting of the following formula IIc:

[0040] [ka] Formula IIc It may be more narrowly defined as

[0041]

[0026] When the retention aid is represented by or includes Formula IIa, (b1) and (b2) represent the molar proportions of the related repeat units, and the combined molar proportion of (b1) and (b2) is equal to the total molar proportion of (b) in Formula II. In other words, repeat unit (b1) is the first repeat unit derived from repeat unit (b) in Formula II, and repeat unit (b2) is the second repeat unit derived from repeat unit (b). Similarly, when the retention aid is represented by or includes Formula IIc, (b1), (b2), and (b3) represent the molar proportions of the related repeat units, and the combined molar proportion of (b1), (b2), and (b3) is equal to the total molar proportion of (b) in Formula II.

[0042] When the retention aid is or includes a nitrogen-containing polymer of Formula IIa, the nitrogen-containing polymer can be partially hydrolyzed poly(n-vinylformamide). The degree of hydrolysis determines the molar amount of each repeating unit. Typically, the partially hydrolyzed poly(n-vinylformamide) is 30 to 70% hydrolyzed, based on the total amount of hydrolyzable functional groups. Alternatively, the partially hydrolyzed poly(n-vinylformamide) can be 30 to 60, 40 to 70, 40 to 60, or about 50% hydrolyzed, based on the total amount of hydrolyzable functional groups. When the retention aid is or includes a nitrogen-containing polymer of Formula IIb, the nitrogen-containing polymer may be referred to as a polyallylamine. Although not required, the weight average molecular weight of the polyallylamine is typically 30,000 to 100,000 daltons. Alternatively, the weight average molecular weight of the polyallylamine may be 30,000 to 90,000, 30,000 to 80,000, 30,000 to 70,000, 40,000 to 90,000, 50,000 to 80,000, 60,000 to 70,000, or about 65,000 daltons. When the retention aid is or includes a nitrogen-containing polymer of Formula IIc, the nitrogen-containing polymer may be referred to as formamide, N-ethenyl-, homopolymer, hydrolyzed N-(3-carboxy-1-oxopropyl)N-[2-hydroxy-3-(trimethylammonio)propyl] derivative, chloride (CAS Registry Number 945630-11-5). Those skilled in the art will readily recognize that multiple reaction routes can be used to synthesize the nitrogen-containing polymer of Formula IIc, but Example 5 of U.S. Pat. No. 8,604,134 discloses a suitable process. The disclosure of U.S. Pat. No. 8,604,134, regarding the nitrogen-containing polymer of Formula IIc, is incorporated herein by reference.

[0043] In certain embodiments, the retention aid is a nitrogen-containing polymer of Formula II, the retention aid comprises: (i) a partially hydrolyzed poly(n-vinylformamide) having a degree of hydrolysis of 30 to 70%, (ii) a nitrogen-containing polymer of Formula II in which the molar proportion of (a) is 100 mol % and Rx is represented by —R3NH2, and (iii) a molar proportion of (b) is 100 mol % and R0 is H,

[0044] [ka] and combinations thereof. In certain embodiments where the retention aid is a nitrogen-containing polymer of Formula II, the retention aid is independently selected from the group consisting of nitrogen-containing polymers of Formula II, wherein the combined molar proportion of (i) (b) and (e) is 100 mole %, and R is independently selected from the group consisting of H,

[0045] [ka] and combinations thereof, (ii) a polyallylamine having a weight average molecular weight of 30,000 to 100,000 Daltons; (iii) a nitrogen-containing polymer of Formula II, in which the molar ratio of (b) is 100 mole %, and R0 is independently selected from the group consisting of H,

[0046] [ka] and combinations thereof, is selected from the group consisting of: In certain embodiments where the retention aid is a nitrogen-containing polymer of Formula II, the retention aid is independently selected from the group consisting of nitrogen-containing polymers of Formula II, wherein the combined molar proportion of (i), (b), and (e) is 100 mole %, and R is independently selected from the group consisting of H,

[0047] [ka] and combinations thereof. (ii) a nitrogen-containing polymer of Formula II, wherein the molar proportion of (a) is 100 mole % and Rx is represented by —R3NH2, and (iii) a polymer selected from the group consisting of formamide, N-ethenyl-, homopolymer, hydrolyzed N-(3-carboxy-1-oxopropyl)N-[2-hydroxy-3-(trimethylammonio)propyl] derivative, chloride (CAS Registry Number 945630-11-5), and combinations thereof.

[0048] In certain embodiments, the retention aid is represented by a nitrogen-containing polymer of Formula I, wherein the combined molar proportion of (b), (c), (d), and (e) is greater than 95 mole %. Alternatively, or in addition, in certain embodiments, where the retention aid is a nitrogen-containing polymer of Formula II, the molar concentration of repeating unit (a) is 0, and thus Formula II is represented by the following Formula III:

[0049] [ka] Formula III When the retention aid is a nitrogen-containing polymer of formula III, the retention aid may be further defined by the following formula IIIa:

[0050] [ka] Formula IIIa It may be further defined as:

[0051] The nitrogen-containing polymer of Formula IIIa may generally be a fully hydrolyzed poly(n-vinylformamide). In other words, unlike the nitrogen-containing polymer of Formula IIa, essentially all of the nitrogen-containing polymer of Formula IIIa is actually hydrolyzed in the nitrogen-containing polymer of Formula IIIa.

[0052] In certain embodiments where the retention aid is a nitrogen-containing polymer of Formula I, the nitrogen-containing polymer has the following Formula IV:

[0053] [ka] Formula IV. When the retention aid is polyacrylamide, the molar ratio of (c) corresponding to the repeating unit (c) is 100 mol %. When the retention aid is polyacrylamide, the weight average molecular weight of the polyacrylamide is usually 5,000,000 to 6,000,000 daltons.

[0054]

[0036] In a different embodiment, the retention aid is a nitrogen-containing polymer selected from the group consisting of (i) polyethyleneimine, (ii) polyaminoamide, (iii) poly(diallyldimethylammonium chloride), and (iv) combinations thereof.

[0037] When the retention aid is polyethyleneimine, the weight average molecular weight of the polyethyleneimine is typically 40,000 to 100,000 daltons. Furthermore, typically, 15 to 35% of the amine groups in the polyethyleneimine are primary amines, and 35 to 65% of the amine groups in the polyethyleneimine are secondary amines, relative to the total number of amine groups in the polyethyleneimine. Alternatively, 20 to 30% or about 25% of the amine groups in the polyethyleneimine are primary amines, and 45 to 55% or about 50% of the amine groups in the polyethyleneimine are secondary amines, relative to the total number of amine groups in the polyethyleneimine.

[0055] The poly(diallyldimethylammonium chloride) may be a low molecular weight poly(diallyldimethylammonium chloride), a high molecular weight poly(diallyldimethylammonium chloride), or a combination thereof. In particular, the low molecular weight poly(diallyldimethylammonium chloride) has a weight average molecular weight of less than 200,000 daltons. In contrast, the high molecular weight poly(diallyldimethylammonium chloride) has a weight average molecular weight of 300,000 to 400,000 daltons.

[0056] In each of the above retention aid embodiments, the nitrogen-containing polymer may have a charge density of >+0.1 meq / g when the pH of the dispersant is 7. Typically, but not necessarily, the charge density of the nitrogen-containing polymer is +5 to +13 meq / g. Furthermore, in each of the above retention aid embodiments, when the nitrogen-containing polymer contains two or more repeat units, the repeat units are typically randomly distributed within the nitrogen-containing polymer. Finally, in each of the embodiments of the present disclosure, the dispersant is typically free of (i.e., does not contain) a fluorine-containing polymer and a fluorine-containing performance additive. The dispersant typically includes a retention aid in an amount of 0.1 to 12 parts by weight per 100 parts by weight of dispersant. Alternatively, the retention aid may be present in the dispersant in an amount of 0.1 to 12, 0.3 to 12, 0.5 to 12, 0.7 to 12, 0.9 to 12, 2.0 to 12, 3.0 to 12, 4.0 to 12, 5.0 to 12, 0.1 to 10, 0.1 to 8, 0.1 to 6, or 0.1 to 4 parts by weight per 100 parts by weight of dispersant. In certain embodiments, the dispersing agent comprises a sizing agent selected from the group consisting of stearates, beeswax, candelilla wax, palmitates, behenates, and combinations thereof. The dispersing agent may also be represented by the following formula II:

[0057] [ka] Formula II In these embodiments, the nitrogen-containing polymer has a charge density >+0.1 meq / g when the pH of the dispersant is 7. In another embodiment, the dispersing agent comprises a sizing agent selected from the group consisting of stearates, beeswax, candelilla wax, palmitates, behenates, and combinations thereof. The dispersing agent may also be represented by the following formula IIa, IIb, and IIc:

[0058] [ka] and combinations thereof. In these embodiments, the nitrogen-containing polymer has a charge density >+0.1 meq / g when the pH of the dispersant is 7.

[0059] In certain embodiments, the dispersant comprises a sizing agent selected from the group consisting of stearates, beeswax, candelilla wax, palmitates, behenates, and combinations thereof. In different embodiments, the retention aid is a nitrogen-containing polymer selected from the group consisting of (i) polyethyleneimine, (ii) polyaminoamide, (iii) poly(diallyldimethylammonium chloride), and (iv) combinations thereof. In one embodiment, the sizing agent is behenate and the retention aid is a nitrogen-containing polymer selected from the group consisting of (i) polyethyleneimine, (ii) polyaminoamide, (iii) poly(diallyldimethylammonium chloride), and (iv) combinations thereof. Furthermore, the nitrogen-containing polymer has a charge density >+0.1 meq / g when the pH of the dispersant is 7.

[0060]

[0044] When the nitrogen-containing polymer is or comprises polyethyleneimine, the polyethyleneimine typically has a weight-average molecular weight of 40,000 to 100,000 daltons, and 20 to 30% of the amine groups in the polyethyleneimine are primary amines and 45 to 55% of the amine groups in the polyethyleneimine are secondary amines, relative to the total number of amine groups in the polyethyleneimine. When the nitrogen-containing polymer is or comprises poly(diallyldimethylammonium chloride), the weight-average molecular weight of the poly(diallyldimethylammonium chloride) is either less than 200,000 daltons or 300,000 to 400,000 daltons.

[0061] In certain embodiments, the dispersing agent comprises a sizing agent selected from the group consisting of stearates, beeswax, candelilla wax, palmitates, behenates, and combinations thereof. In such embodiments, the retention aid may also comprise or be a polyacrylamide having a weight average molecular weight of 5,000,000 to 6,000,000 Daltons.

[0062]

[0046] Although not required, the dispersant may also contain a surfactant to enhance the stability of the dispersant. The surfactant may be an anionic surfactant, a nonionic surfactant, a cationic surfactant, an amphoteric surfactant, or a polymer surfactant. Among these, anionic surfactants, nonionic surfactants, and cationic surfactants are typically used. When a surfactant is included, it is typically present in an amount of 0.1 to 5 parts by mass per 100 parts by mass of the dispersant. Suitable examples of anionic surfactants include alkyl carbonate compounds, alkyl sulfate compounds, and alkyl phosphates. Specific examples of anionic surfactants include dioctyl sulfosuccinate sodium salt, sodium dodecyl sulfate, and sodium lauryl sulfate. Suitable examples of nonionic surfactants include ethylene oxide and / or propylene oxide adducts of alcohols having 1 to 18 carbon atoms, ethylene oxide and / or propylene oxide adducts of alkylphenols, and ethylene oxide and / or propylene oxide adducts of alkylene glycols and / or alkylenediamines. Suitable examples of cationic surfactants include primary to tertiary amines, pyridinium salts, alkylpyridinium salts, and quaternary ammonium salts such as quaternary alkyl halide ammonium salts.

[0063] Without being bound by any particular theory, it is believed that a first portion of the amine groups of the retention aid bond with oxygen atoms present in the ester and / or acid of the sizing agent via hydrogen or electrostatic bonding. Furthermore, it is believed that the remaining portion of the amine groups bond or associate with hydroxyl groups present on fibers, such as cellulosic pulp fibers, that are also included in the treated article. In other words, the retention aid bonds or associates with both the sizing agent and the fibers. As described further below, during the process of making the treated article, the binding of the retention aid to both the sizing agent and the fibers fixes, holds, tethers, incorporates, orients, etc., the retention aid between and on the surface of adjacent fibers, forming a dense network / matrix. Furthermore, it is believed that certain sizing agents and retention aids of the present disclosure have strong interactions that result in effective dispersion of the retention aid and sizing agent throughout the treated article. Treated articles prepared using the dispersants of the present disclosure have relatively fewer air pockets and channels within the treated article compared to conventionally treated articles prepared without the dispersants of the present disclosure. This result is believed to be achieved because the sizing agents and retention aids effectively fill or seal these air pockets and / or channels. This reduction in the relative amount of air pockets and channels is significant, providing treated articles with enhanced barrier properties. Specifically, treated articles prepared using the dispersants of the present disclosure are relatively more resistant to both water and oil penetration compared to conventionally treated articles.

[0064] The present disclosure also provides a treated article formed from the dispersant. The treated article includes a retention aid, a sizing agent, and a fiber. The type of fiber is not limited to a particular type, but in certain embodiments, it may be advantageous to select a fiber that has the ability to bond with the amine groups of the retention aid.

[0065]

[0049] The article to be treated may be a paper product, food packaging, non-food contact packaging, wood or building materials, nonwoven fabrics, molded fibers, such as paper plates, take-out containers, bowls, etc., or any paper-like substrate, particularly one where water and / or oil resistance is advantageous.

[0066] The fibers may be natural, synthetic, semi-synthetic, inorganic, or combinations thereof. Specific examples of natural fibers include those derived from plants or wood, which may be referred to as cellulosic fibers, such as bamboo, bentgrass, sawgrass, bagasse, straw, hay, spruce, pine, fir, larch, eucalyptus, aspen, and birch. Specific examples of synthetic fibers include polyamide, polyester, polyvinyl alcohol, polyacrylonitrile, polyvinyl chloride, and polypropylene. In certain embodiments, the fibers are pulp fibers from bleached and unbleached sulfate (kraft) hardwood or softwood pulp, groundwood pulp, regenerated cellulose fibers, and bleached chemithermomechanical pulp (BCTMP), as well as combinations thereof.

[0067] In one embodiment, the treated article (i.e., the dried, final treated article immediately prior to consumer use) may comprise, by weight, 16 to 99.8 parts of fiber, 0.1 to 80 parts of sizing agent, and 0.1 to 4 parts of retention aid, each based on 100 parts of treated article. Alternatively, the treated article may comprise, by weight, 47 to 99.8 parts of fiber, 1 to 50 parts of sizing agent, and 0.2 to 3 parts of retention aid, each based on 100 parts of treated article. Alternatively, the treated article may comprise, by weight, 78 to 97.2 parts of fiber, 2.5 to 20 parts of sizing agent, and 0.3 to 2 parts of retention aid, each based on 100 parts of treated article.

[0068] The treated article may also include ingredients in addition to retention aids, sizing agents, and fibers. For example, the treated article may further include starch, resins, crosslinkers, catalysts, inorganic or organic fillers, coagulants, support agents (e.g., dextrin), retention agents, flocculating agents, buffers, bactericides, biocides, sequestering agents, hydrophobizing agents (e.g., alkenyl succinic anhydrides and / or alkyl ketene dimers), and the like, as well as various combinations of such ingredients.

[0053] Specific examples of starches suitable for the treated article include, but are not limited to, hydroxyethyl starch, cationic starch, amphoteric starch, oxidized starch, phosphorylated starch, enzymatically degraded starch, and combinations thereof. Specific examples of resins suitable for the treated article include, but are not limited to, polyvinyl alcohol, polyvinyl chloride latex, polyvinyl alcohol, and the like.

[0055] Specific examples of crosslinking agents suitable for the treated article include, but are not limited to, urea or melamine-formaldehyde condensates or precondensates, methylol-dihydroxyethylene-urea or its derivatives, uron, methylol-ethylene-urea, methylol-propylene-urea, methylol-triazone, dicyandiamide-formaldehyde condensates, methylol carbamate, methylol (meth)acrylamide, polymers thereof, divinyl sulfone, polyamides or cationic derivatives thereof, pyridinium salts of ethylene glycol chloromethyl ether, glyoxal, and combinations thereof. Specific examples of catalysts suitable for the purpose of the article being treated include, but are not limited to, ammonium chloride, alkanolamine salts, zirconium acetate salts, and combinations thereof.

[0057] Specific examples of inorganic fillers include silica, alumina, sericin, resin powder, talc, kaolin, precipitated calcium carbonate, ground calcium carbonate, bentonite, clay, titanium dioxide, etc., but are not limited to these. The particular components present in the treated article, as well as the amounts of each of them, will depend on the particular fibers used in the slurry, as well as the desired end use of the treated article.

[0069]

[0059] The present disclosure also provides a method for producing a treated article. The method includes providing a slurry containing fibers. The slurry may be provided by any suitable method. When the step of providing a slurry includes preparing a slurry, the slurry can be prepared according to methods generally known in the art. For example, in embodiments where the fibers are cellulosic fibers, the slurry can be prepared by a mechanical pulping process; a thermomechanical pulping process; a chemi-thermomechanical pulping process; a chemical pulping process, e.g., a recycled pulping process such as the kraft process, sulfite process, and soda process; an organic solvent pulping process, or the like. Alternatively, the slurry can be prepared by purchasing or otherwise obtaining dry cellulosic fibers. This fiber is commonly referred to in the art as "market pulp." The fibers may be bleached depending on the desired appearance of the treated article. If bleached, the fibers may be bleached with, for example, chlorine, chlorine dioxide, oxygen, ozone, hydrogen peroxide, or the like. Typically, the fibers are present in the slurry in an amount of from greater than 0 to 5 parts by weight, alternatively from 0.2 to 3.75 parts by weight, alternatively from 0.3 to 3 parts by weight, per 100 parts by weight of the slurry. Of course, it should be understood that the fibers may be present in the slurry in amounts other than those indicated above, depending on the presence or absence of various optional ingredients, as described in more detail below. The remainder of the slurry typically comprises water or a combination of water and a water-miscible solvent. In certain embodiments where the fibers are cellulose fibers, the fibers of the slurry are typically refined. Typically, the fibers of the slurry are refined by subjecting the slurry to shear forces that separate cellulose clumps or fiber clusters into individual fibers. Generally, the fibers of the slurry are not refined until the slurry is prepared or provided; i.e., "market pulp" is typically not refined until it is reconstituted in water to form a slurry. The method further includes combining a dispersant with the slurry. In this embodiment of the method, those skilled in the art will recognize that the sizing agent may more generally be referred to as an internal sizing agent. Once combined, the slurry and dispersant are mixed, typically to distribute the dispersant throughout the slurry.

[0070] The method further includes forming a treated article from the slurry containing the dispersant. Typically, the slurry is formed into at least one sheet. For clarity, at least one sheet will be referred to herein simply as a "sheet," which should be understood to encompass even a plurality of sheets. Methods for forming treated articles in sheet form are well known in the art. For example, sheets are typically formed on a metal substrate, such as stainless steel, or what is known in the art as monofilament wire. The relative dimensions (e.g., thickness, length, width) of the sheet will vary depending on various factors, such as the desired end use of the treated article formed by the method. Once formed, the sheet is typically dried to remove excess solvent (e.g., water and / or water-miscible solvent). The sheet may be dried by vacuum and / or foil dewatering. Alternatively, the sheet may be dried by press dewatering, in which pressure is applied to the sheet. The pressure utilized when the sheet is dried by press dewatering is typically 0.5 to 200 psig. Additionally, the sheet may be dried via contact dewatering, in which the sheet is dried via exposure to a papermaker's fabric, which absorbs excess water and / or water-miscible solvent from the sheet. Contact drying may also be performed by contacting the sheet with a metal roller having a smooth surface. The metal roller utilized in contact drying is typically heated, for example, to 150 to 280°F. Any combination of these methods, or additional methods known in the art for drying a sheet to remove excess water and / or water-miscible solvent, may be used. In certain embodiments, all of the above sheet drying methods are utilized, typically in the order in which they are presented above.

[0071]

[0065] The present disclosure also provides a method of providing a surface-treated article. The method includes forming a sheet from a fiber slurry (e.g., a pulp slurry) as described above, except that a dispersant is not mixed with the fiber slurry before forming the sheet. Instead, a dispersant is applied to at least one surface of the sheet after it is formed. In this embodiment of the method, those skilled in the art will recognize that a sizing agent may more generally be referred to as an external sizing agent. The dispersant may be applied to the sheet before excess water is removed from the sheet or when the sheet is considered dry.

[0072]

[0066] The process of applying the dispersant to at least one surface of the sheet is not particularly limited, as long as it can create intimate contact between the dispersant and the sheet. For example, the dispersant can be applied to at least one surface of the sheet by spraying, brushing, padding, size press coating, metering size press coating, film press coating, gravure coating, flexo coating, roller coating, rotor dampening, foaming, gate roll coating, bill blade coating, bar coating, intaglio coating, reverse roll coating, skid roll coating, transfer (offset) roll coating, knife coating, knife over roll coating, J-coating, air knife coating, curtain coating, and combinations thereof. In certain embodiments, the method of forming the treated article combines both of the above methods. Specifically, in this embodiment, the dispersant is added to the slurry before forming the sheet, and then applied to at least one surface of the sheet after it is formed. Those skilled in the art will recognize that this method includes both internal and external sizing steps.

[0073]

[0068] The present disclosure also provides a further method for producing a treated article. Unlike previous methods, this method does not form a dispersion and then add the dispersion to the slurry. Instead, the retention aid and sizing agent are not first combined into a single composition, but are added separately to the slurry. In other words, instead of adding a dispersion containing the retention aid and sizing agent to the slurry, the retention aid is added to the slurry without pre-combining it with the sizing agent. Similarly, the sizing agent is added to the slurry without pre-combining it with the retention aid. In this embodiment, the order of addition of the sizing agent and retention aid is not limited. For example, the sizing agent may be added to the slurry, followed by the retention aid, or vice versa. Of course, the sizing agent and retention aid can also be added simultaneously without pre-mixing.

[0074]

[0069] The present disclosure also provides another embodiment of a dispersant that differs from the previous embodiment. In this embodiment, the dispersant comprises a reaction product of a sizing agent and a retention aid. Although not required, the reaction product can be formed when an amine group present on the retention aid reacts with an alkyl acid of the sizing agent. In certain embodiments, the dispersant may comprise a reaction product rather than separately comprising a sizing agent and a retention aid. Alternatively, the dispersant may comprise a solvent, a retention aid, a sizing agent, and further comprise a reaction product between the retention aid and the sizing agent. For example, the reaction product may be an amidation reaction between an amine group, usually a primary amine group, of the retention aid and an alkyl acid of the sizing agent.

[0075] In one embodiment, the reaction product is formed when the retention aid is polyethyleneimine and a sizing agent, for example, when the sizing agent comprises an alkyl acid (e.g., stearic acid). In this embodiment, the retention aid is typically selected from the group consisting of:

[0076] [ka] (wherein n represents the number of repeating units) It is represented by the chemical structure shown below.

[0077] In another embodiment, the reaction product comprises a sizing agent and a compound represented by the following formula IIa:

[0078] [ka] Formula IIa wherein: The reaction product has the following formula IIa':

[0079] [ka] Formula IIa' (wherein in Formula IIa', R6 represents C(=O)R1) Although not required, R1 is typically a straight or branched alkyl or alkenyl having from 17 to 21 carbon atoms.

[0080] In another embodiment, the reaction product is a compound of a sizing agent and a compound of the following formula IIb:

[0081] [ka] Formula IIb wherein: The reaction product has the following formula IIb'

[0082] [ka] Formula IIb' (wherein R6 represents C(=O)R1) Although not required, R1 is typically a straight or branched alkyl or alkenyl having from 17 to 21 carbon atoms.

[0083] In another embodiment, the reaction product comprises a sizing agent and a compound of the following formula IIc:

[0084] [ka] Formula IIc wherein the reaction product has the following formula IIc':

[0085] [ka] Formula IIc' (wherein R6 represents C(=O)R1) Although not required, R1 is typically a straight or branched alkyl or alkenyl having from 17 to 21 carbon atoms. In another embodiment, the reaction product can be more generally described as Formula I, a reaction product of a primary amine and at least one of (a), (b), or (c) comprising an alkyl acid of the sizing agent. Typically, the alkyl acid has 17 to 21 carbon atoms. In each case, the primary amine reacts with the alkyl acid such that the primary amine (NH) group is replaced with NC(=O)R. Typically, R is an alkyl chain having 17 to 21 carbon atoms. [Example]

[0086] Dispersants were first prepared and then used in conjunction with pulp slurries to prepare and evaluate treated articles. The composition of each dispersant is shown below. To prepare the pulp slurries, wood pulp was mixed in water to dilute the wood pulp to approximately 0.3% pulp solids by weight, based on the total weight of the pulp slurry. The dispersant was then combined with the pulp slurry and further mixed. Sheets were then formed in a Noram TAPPI handsheet former and dried at 260°F in an Adirondack drum dryer. The resulting dried sheets were conditioned for at least 4 hours in a humidity-controlled chamber at 23°C and 50% relative humidity. The dried sheets were then evaluated for water repellency at room temperature and at 85°C. The dried sheets were also evaluated for corn oil repellency at room temperature. The dried sheets were also evaluated in the Cobb Water Absorbency and Breakthrough Cobb Oil Tests. The results are shown in Table I below.

[0087] To evaluate water repellency, a drop of water or corn oil at a specified temperature was placed on the sheet. After 15 seconds, the sheet was evaluated to determine whether the specified liquid bled through the sheet. The results were recorded qualitatively as pass (P) or fail (F).

[0088] To evaluate Cobb water absorbency, a sheet was first weighed and clamped in a Cobb ring apparatus. Exactly 100 grams of room temperature tap water was weighed and placed on the sheet in the Cobb ring apparatus and allowed to sit for 1 minute 45 seconds. The water was then poured out and the sheet was unclamped. The sheet was then sandwiched between two sheets of sheet-forming blotter paper, and a 10 kg Cobb roller was rolled once forward and once reverse across the sheet (two passes total, each pass in the opposite direction). The sheet was then immediately weighed, and the initial mass and exposed mass were used to calculate absorbency.

[0089] To evaluate the breakthrough Cobb oil test, the sheet was first weighed. A clean circle of a Whatman #4 qualitative circle was placed under the sheet as an absorbent blotter for breakthrough. Next, a 20 mm diameter template was placed on the sheet to define the initial exposure area. A 0.5 gram oil sample was then collected using a pipette, and corn oil was then added to the sheet within the 20 mm diameter template. The oil was spread across the sheet until it was evenly distributed across the template. After the oil was delivered to the sheet, the pipette was weighed to determine the exact mass of oil added to the sheet. Once the oil was evenly distributed, the template was removed, and a 300 gram weight was placed centered on top of the oil and allowed to sit for 120 seconds. Next, a sheet-forming blotter was placed on top of the sheet, and a 10 kg Cobb roller was rotated across the sheet once forward and once backward (a total of two passes, each pass in the opposite direction) to absorb excess oil on the surface of the sheet. The exposed sheet and Whatman #4 qualitative circle were then weighed and the % absorbance calculated.

[0090] Additional treated articles were prepared and evaluated using the following methods. A pulp slurry was made from wood pulp by mixing the wood pulp in water to dilute the wood pulp to about 0.3% by weight of solid pulp, based on the total weight of the pulp slurry. A diluted solution of retention aid was then combined with the slurry and stirred for 60 seconds. A wax dispersant was then added to the slurry and mixed for an additional minute. Sheets were then formed in a Noram TAPPI handsheet former and dried in an Adirondack drum dryer at 260°F. The resulting dried sheets were conditioned for at least four hours in a humidity-controlled chamber at 23°C and 50% relative humidity. The compositions of the wax dispersant and retention aid are described below. Tests performed on the resulting sheets are reported in Table I below.

[0091] [Table 1]

[0092] [Table 2]

[0093] [Table 3]

[0094] [Table 4]

[0095] [Table 5]

[0096] [Table 6]

[0097] [Table 7]

[0098] [Table 8] The results shown in Table I above demonstrate that the dispersants of the present disclosure, which include a retention aid and a sizing agent containing a wax or component thereof having an acid number between 10 mg and 220 mg KOH / g, produce superior articles when the articles are treated with the dispersant.

[0099]

[0082] All combinations of the foregoing embodiments throughout this disclosure are expressly contemplated by this specification in one or more non-limiting embodiments, even if such disclosure is not set forth verbatim in a single paragraph or section above. In other words, an expressly contemplated embodiment may include any one or more elements described above selected and combined from any portion of this disclosure.

[0083] One or more of the above values ​​may be ±5%, ±10%, ±15%, ±20%, ±25%, etc., as long as the variation remains within the scope of the present disclosure. Unexpected results may be obtained from each member of the Markush group, independent of all other members. Each element may be relied upon individually and / or in combination, providing adequate support for particular embodiments within the scope of the appended claims. The subject matter of all combinations of independent and dependent claims (both singly and multiple dependent) is expressly contemplated herein. The present disclosure is illustrative, containing in descriptive terms rather than limiting. Many modifications and variations of the present disclosure are possible in light of the above teachings, and the present disclosure may be practiced otherwise than as specifically described herein.

[0084] Any ranges and subranges relied upon in describing various embodiments of the present disclosure should also be understood to fall within the scope of the appended claims, both individually and collectively, and to describe and contemplate all ranges, including integer and / or fractional values ​​therein, even if such values ​​are not expressly set forth herein. Those skilled in the art will readily recognize that the recited ranges and subranges fully describe and enable various embodiments of the present disclosure, and that such ranges and subranges may be further delineated into related halves, thirds, quarters, fifths, etc. As merely an example, the range "0.1 to 0.9" may be further delineated into a lower third, i.e., 0.1 to 0.3, a middle third, i.e., 0.4 to 0.6, and an upper third, i.e., 0.7 to 0.9, which are individually and collectively within the scope of the appended claims and may be relied upon individually and / or collectively to provide adequate support for particular embodiments within the scope of the appended claims. Additionally, with respect to language defining or modifying ranges, such as "at least," "greater than," "less than," "less than or equal to," etc., it should be understood that such language includes subranges and / or upper or lower limits. As another example, the range "at least 10" inherently includes subranges of at least 10 to 35, at least 10 to 25, 25 to 35, etc., each of which may be relied upon individually and / or collectively to provide appropriate support for particular embodiments within the appended claims. Finally, individual numbers within a disclosed range may be relied upon to provide appropriate support for particular embodiments within the appended claims. For example, the range "1 to 9" includes various individual integers (e.g., 3) as well as individual numbers containing decimal points (or fractions) (e.g., 4.1), which may depend on and provide appropriate support for particular embodiments within the appended claims. The present application includes the following aspects. [Section 1] 1. A dispersant for use in a process for making a treated article, comprising: solvent, A sizing agent containing a natural wax or a component thereof, having an acid value of 10 mg to 220 mg (KOH / g) as measured in accordance with USP 401; 1. A retention aid comprising a nitrogen-containing polymer, the nitrogen-containing polymer independently comprising: (i) Formula I:

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Claims

1. 1. A dispersant for use in a process for making a treated article, said dispersant comprising: Contains no fluoride solvent, a sizing agent comprising a wax or component thereof having an acid value of 10 mg to 220 mg KOH / g as measured in accordance with USP 401, said sizing agent being selected from the group consisting of stearates, beeswax, candelilla wax, palmitates, behenates, and combinations thereof; and a retention aid comprising a nitrogen-containing polymer represented by Formula III: 【Chemistry 1】 In the formula, (b) and (e) individually represent the molar ratio (mol %) of each repeat unit contained in the nitrogen-containing polymer of Formula III, and the sum of (b) and (e) is 100 mol %; R ０ are independently H, 【Chemistry 2】 and combinations thereof; Y is independently H, —OH, —R １ , -OR １ , -NR １ R １ , -NH ２ and combinations thereof; R １ is independently selected from H, straight or branched alkyl or alkenyl containing up to 22 carbons, and combinations thereof; R ２ are independently selected from H, monosaccharide, oligosaccharide, polysaccharide moieties, straight or branched chain alkyl or alkenyl groups of up to 22 carbons optionally containing hydroxyl or aldehyde groups, and combinations thereof; R ３ are independently selected from linear or branched alkyl or alkenyl containing up to 22 carbons or combinations thereof; R ４ are independently selected from linear or branched alkyl groups containing up to 18 carbons, optionally substituted with hydroxyl groups, and combinations thereof; R ５ are independently H, —OH, —COOH, —COOR １ , -OCOR １ , -R １ , -R １ OH, -OR １ , -CONH ２ , -CONHCHOHCHO, -NR １ , -NR １ R １ , -R １ NH ２ , -NH ２ and combinations thereof; A is independently C═O, —CH ２ and combinations thereof; X ― are independently anions, Dispersant.

2. R ０ is H, and the nitrogen-containing polymer of Formula III further comprises a nitrogen-containing polymer of Formula IIIa: 【Transformation 3】 The dispersant according to claim 1, wherein

3. 10. The dispersant of claim 1, wherein the nitrogen-containing polymer has a charge density at pH 7 of >+0.1 meq / g.

4. The sizing agents are independently selected from the group consisting of stearates, beeswax, candelilla wax, palmitates, behenates, and combinations thereof; 4. The dispersant of any one of claims 1 to 3, wherein the sizing agent is present in an amount of 10 to 50 parts by weight per 100 parts by weight of the dispersant, and the retention aid is present in an amount of 0.1 to 12 parts by weight per 100 parts by weight of the dispersant.

5. A dispersant described in any one of claims 1 to 3, wherein the sizing agent is stearic acid.

6. The dispersant according to any one of claims 1 to 3, Fiber, and a second solvent that is the same as or different from the solvent of the dispersant.

7. A method for preparing a dispersant according to any one of claims 1 to 3, comprising mixing the solvent, the sizing agent, and the retention aid.

8. 1. A dispersant for use in a process for making a treated article, said dispersant comprising: Contains no fluoride a solvent, and the reaction product of I and II, I is a sizing agent containing a wax or a component thereof having an acid value of 10 mg to 220 mg (KOH / g) as measured in accordance with USP 401, and the sizing agent is selected from the group consisting of stearates, beeswax, candelilla wax, palmitates, behenates, and combinations thereof; The II is a retention aid comprising a nitrogen-containing polymer represented by Formula III: 【Chemistry 4】 In the formula, (b) and (e) individually represent the molar ratio (mol %) of each repeat unit contained in the nitrogen-containing polymer of Formula III, and the sum of (b) and (e) is 100 mol %; R ０ are independently H, 【Transformation 5】 and combinations thereof; Y is independently H, —OH, —R １ , -OR １ , -NR １ R １ , -NH ２ and combinations thereof; R １ is independently selected from H, straight or branched alkyl or alkenyl containing up to 22 carbons, and combinations thereof; R ２ are independently selected from H, monosaccharide, oligosaccharide, polysaccharide moieties, straight or branched chain alkyl or alkenyl groups of up to 22 carbons optionally containing hydroxyl or aldehyde groups, and combinations thereof; R ３ are independently selected from linear or branched alkyl or alkenyl containing up to 22 carbons or combinations thereof; R ４ are independently selected from linear or branched alkyl groups containing up to 18 carbons, optionally substituted with hydroxyl groups, and combinations thereof; R ５ are independently H, —OH, —COOH, —COOR １ , -OCOR １ , -R １ , -R １ OH, -OR １ , -CONH ２ , -CONHCHOHCHO, -NR １ , -NR １ R １ , -R １ NH ２ , -NH ２ and combinations thereof; A is independently C═O, —CH ２ and combinations thereof; X ― are independently anions, Dispersant.

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