Neutralized multi-amine dispersant compositions

Abstract

The described composition comprises: (a) a polymeric dispersant comprising: (i) at least two polyether side groups per molecule on average; and (ii) at least two amino groups per molecule on average; and (b) a functionalized acid component comprising a sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; and wherein at least about 60% of the amino groups present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component. Pigment dispersions and / or ink formulations comprising these compositions are also described, as well as various methods for preparing and / or using these compositions, pigment dispersions and / or ink formulations.

Description

Technical Field

[0001] The disclosed technology relates to compositions comprising polymeric dispersants having an average of at least two amine groups per molecule, which are at least partially neutralized by a functionalized acid component (e.g., salt formation). Pigment dispersions and ink formulations comprising such compositions are also described, as well as methods for manufacturing and / or using such materials. Prior Technology

[0002] Many conventional packaging inks are manufactured around a common formulation of pigments, binders, tackifiers, and solvents. Illustrative ink formulations are described, for example, in JP 2017-39896A. In many cases, the binder acts as a dispersing agent and prevents pigment particles from re-aggregating after grinding. However, in other cases, the use of a custom dispersant can significantly improve ink properties such as stability, pigment content, and color development. Typically, polymeric dispersants can be acid-functional, amine-functional, or nonionic. However, due to compatibility issues that may arise when using amine-functional dispersants with other components in the formulation, nonionic or acidic dispersants are used in this application.

[0003] Pigment Yellow 13 is an important pigment used in packaging inks. It has been observed that Dispersed Yellow 13 uses polymeric dispersants, preferably with strongly amine functional groups, to ensure adequate anchoring of the dispersant to the pigment surface. One type of binder used in packaging inks is nitrocellulose, as seen in, for example, JP 2018-199802A; it has been found that amine-functionalized dispersants interact adversely with such binders, leading to gel formation over time, which would be disastrous for a fully formulated ink composition. Similarly, organometallic complexes (such as titanates) have a long history in packaging ink formulations, as seen in, for example, WO 2012 / 028882 A1, to provide adhesion to low surface energy substrates (such as polyethylene or oriented polypropylene) when used in conjunction with binders. However, organometallic complexes readily react undesirably with amine-functionalized dispersants, re-gelling and / or increasing viscosity.

[0004] Polymer dispersants having a plurality of amine groups are described in, for example, the following documents: US 7,767,750 B2, US 8,859,675 B2, US 8,987,374 B2, and US 9,416,280 B2. These documents do not disclose polymer dispersants having an average of at least two amine groups per molecule, wherein at least about 60% of the amine groups present in the polymer dispersant are individually neutralized (e.g., salted) by a molecule of a functionalized acid component. Summary of the Invention

[0005] Therefore, the disclosed techniques provide compositions comprising polymeric dispersants having an average of at least two amine groups per molecule, wherein at least about 60% of the amine groups present in the polymeric dispersant are individually neutralized by molecules of a functionalized acid component, as described herein. It has been found that such compositions can at least partially mitigate problematic interactions that amine-functionalized dispersants may have with other components by using sulfonic acid or phosphoric acid relative ions to form amine salts, thereby producing suitable efficacy with certain components, such as additives (e.g., organometallic complexes) and / or binders (e.g., nitrocellulose).

[0006] The subject matter disclosed herein provides a composition comprising: (a) a polymeric dispersant comprising: (i) at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; and (ii) at least two amino groups per molecule, wherein the at least two amino groups are not present in the at least two polyether side groups; and (b) a functionalized acid component comprising sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; and wherein at least about 60% of the amino groups present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component.

[0007] Also provided is a pigment dispersion comprising: (a) a pigment; and (b) a polymeric dispersant for the pigment, the polymeric dispersant comprising: (i) at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; and (ii) at least two amine groups per molecule, wherein the at least two amine groups are not present in the at least two polyether side groups; and (c) a functionalized acid component comprising sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; and wherein at least about 60% of the amine groups present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component.

[0008] Ink formulations are also provided, comprising: (a) one or more pigment dispersions described herein; (b) solvents; (c) binders; and (d) at least one additional additive.

[0009] A method for producing a pigment dispersion is also provided, comprising the steps of combining a pigment, a polymeric dispersant for the pigment, and a functionalized acid component in any order, and the step of grinding the pigment as appropriate, wherein: (a) the polymeric dispersant comprises: (i) at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; (ii) at least (a) two amine groups, wherein the at least two amine groups are not present in the at least two polyether side groups; (b) the functionalized acid component includes sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; (c) at least about 60% of the amine groups present in the polymer dispersant are individually neutralized by the molecules of the functionalized acid component; and (d) the step of grinding the pigment as appropriate: (i) not performed; (ii) performed on the pigment alone before adding the polymer dispersant and / or the functionalized acid component; or (iii) performed on a combination of the pigment and the polymer dispersant and / or the functionalized acid component.

[0010] A method for manufacturing an ink formulation is also provided, comprising: (a) performing one or more methods described herein for forming one or more pigment dispersions; and (b) adding to the pigment dispersion the following components: (i) a solvent; (ii) a binder; and (iii) at least one additional additive.

[0011] The following embodiments cover the subject matter of this invention:

[0012] 1. A composition comprising: (a) a polymeric dispersant comprising: (i) at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; and (ii) at least two amino groups per molecule, wherein the at least two amino groups are not present in the at least two polyether side groups; (b) a functionalized acid component comprising sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; and wherein at least 60% of the amino groups present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component.

[0013] 2. The composition as in Example 1, wherein the polymer dispersant comprises an average of 2 to 200 polyether side groups per molecule.

[0014] 3. The composition as in Example 1 or Example 2, wherein 50% to substantially all of the monomer units of the polyether side groups are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units.

[0015] 4. The composition of any one of Examples 1 to 3, wherein the ratio of the number of poly(ethylene oxide) monomer units to the number of poly(propylene oxide) monomer units is from 0:100 to 90:10.

[0016] 5. The composition of any one of Examples 1 to 4, wherein the polyether side groups account for at least 65% by weight of the polymer dispersant based on the total weight of the polymer dispersant.

[0017] 6. The composition of any one of Examples 1 to 5, wherein the polymeric dispersant comprises an average of 2 to 500 amine groups per molecule.

[0018] 7. The composition of any one of Examples 1 to 6, wherein the functionalized acid component comprises a sulfonic acid functionalized with at least one of aromatic or aliphatic functional groups.

[0019] 8. The composition of any one of Examples 1 to 7, wherein the functionalized acid component comprises dodecylbenzenesulfonic acid.

[0020] 9. A composition as described in any of Examples 1 to 8, wherein the aromatic functional group is a C6-C10 aromatic group that has been substituted, as appropriate.

[0021] 10. A composition as described in any one of Examples 1 to 9, wherein the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C8-C22 hydrocarbon group.

[0022] 11. The composition of any one of Examples 1 to 6, wherein the functionalized acid component comprises at least one compound according to the following general formula: Wherein: R1 is a straight-chain or branched-chain, saturated or unsaturated C8-C22 hydrocarbon group; R2 is an aromatic functional group, which may be a substituted C6-C10 aromatic group; W is phosphorus or sulfur; m is 1 or 2, where m is 1 or 2 when W is sulfur, and m is 1 when W is phosphorus; n is 1 or 2, where n is 1 when W is sulfur, and n is 2 when W is phosphorus; s is 0 or 1; t is 0 or 1; conditional s and t cannot both be 0.

[0023] 12. The composition as in Example 11, wherein W is sulfur.

[0024] 13. The composition as in Example 11 or Example 12, wherein s is 1 and t is 1.

[0025] 14. A composition as described in any of Examples 1 to 13, wherein at least about 75% of the amine groups present in the polymeric dispersant are individually neutralized by the molecules of the functionalized acid component.

[0026] 15. A composition as described in any of Examples 1 to 14, wherein at least about 95% of the amine groups present in the polymeric dispersant are individually neutralized by the molecules of the functionalized acid component.

[0027] 16. A pigment dispersion comprising: (a) a pigment; and (b) a polymeric dispersant for the pigment, the polymeric dispersant comprising: (i) at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; and (ii) at least two amino groups per molecule, wherein the at least two amino groups are not present in the at least two polyether side groups; and (b) a functionalized acid component comprising sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; and wherein at least 60% of the amino groups present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component.

[0028] 17. The pigment dispersion of Example 16, wherein the polymer dispersant comprises an average of 2 to 200 polyether side groups per molecule.

[0029] 18. The pigment dispersion of Example 16 or Example 17, wherein 50% to substantially all of the monomer units of the polyether side groups are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units.

[0030] 19. The pigment dispersion of any one of Examples 16 to 18, wherein the ratio of the number of poly(ethylene oxide) monomer units to the number of poly(propylene oxide) monomer units is from 0:100 to 90:10.

[0031] 20. A pigment dispersion as described in any one of Examples 16 to 19, wherein the polyether side groups account for at least 65% by weight of the polymer dispersion based on the total weight of the polymer dispersion.

[0032] 21. A pigment dispersion as described in any of Examples 16 to 20, wherein the polymeric dispersant comprises an average of 2 to 500 amine groups per molecule.

[0033] 22. The pigment dispersion of any one of Examples 16 to 21, wherein the functionalized acid component comprises a sulfonic acid functionalized with at least one of aromatic or aliphatic functional groups.

[0034] 23. The pigment dispersion of any one of Examples 16 to 22, wherein the functionalized acid component comprises dodecylbenzenesulfonic acid.

[0035] 24. A pigment dispersion of any one of Examples 16 to 23, wherein the aromatic functional group is, where appropriate, a substituted C6-C10 aromatic group.

[0036] 25. The pigment dispersion of any one of Examples 16 to 24, wherein the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C8-C22 hydrocarbon group.

[0037] 26. The pigment dispersion of any one of Examples 16 to 25, wherein the functionalized acid component comprises at least one compound according to the following general formula: Wherein: R1 is a straight-chain or branched-chain, saturated or unsaturated C8-C22 hydrocarbon group; R2 is an aromatic functional group, which may be a substituted C6-C10 aromatic group; W is phosphorus or sulfur; m is 1 or 2, where m is 1 or 2 when W is sulfur, and m is 1 when W is phosphorus; n is 1 or 2, where n is 1 when W is sulfur, and n is 2 when W is phosphorus; s is 0 or 1; t is 0 or 1; conditional s and t cannot both be 0.

[0038] 27. The pigment dispersion of Example 26, wherein W is sulfur.

[0039] 28. The pigment dispersion of Example 26 or Example 27, wherein s is 1 and t is 1.

[0040] 29. A pigment dispersion as described in any of Examples 16 to 28, wherein at least about 75% of the amine groups present in the polymeric dispersant are individually neutralized by the molecules of the functionalized acid component.

[0041] 30. A pigment dispersion as described in any of Examples 16 to 29, wherein at least about 95% of the amine groups present in the polymeric dispersant are individually neutralized by the molecules of the functionalized acid component.

[0042] 31. An ink formulation comprising: (a) a pigment dispersion as described in any one of Examples 16 to 30; (b) a solvent; (c) a binder; and (d) at least one additional additive.

[0043] 32. The ink formulation of Example 31, wherein the solvent is a polar solvent.

[0044] 33. The ink formulation of Example 31 or Example 32, wherein the adhesive is a polymer adhesive.

[0045] 34. An ink formulation as described in any of Examples 31 to 33, wherein the at least one additional additive comprises 1 to 5 additional additives.

[0046] 35. An ink formulation as described in any of Examples 31 to 34, wherein the at least one additional additive comprises at least one of a wetting agent, a stabilizer, a tackifier, a wax, or a defoamer.

[0047] 36. A method for producing a pigment dispersion, comprising the steps of combining a pigment, a polymeric dispersant for the pigment, and a functionalized acid component in any order, and the step of grinding the pigment as appropriate, wherein: (a) the polymeric dispersant comprises: (i) at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; (ii) and at least two polyether side groups per molecule. (a) at least two amine groups, wherein the at least two amine groups are not present in the at least two polyether side groups; (b) the functionalized acid component includes sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; (c) at least 60% of the amine groups present in the polymer dispersant are individually neutralized by the molecules of the functionalized acid component; and (d) the step of grinding the pigment as appropriate: (i) not performed; (ii) performed on the pigment alone before adding the polymer dispersant and / or the functionalized acid component; or (iii) performed on a combination of the pigment and the polymer dispersant and / or the functionalized acid component.

[0048] 37. The method of Example 36, wherein the polymer dispersant and the functionalized acid component are combined before the pigment is added, wherein the step of grinding the pigment is performed, as appropriate, before or after the pigment is added to the combination of the polymer dispersant and the functionalized acid component.

[0049] 38. The method of Example 36, wherein the polymer dispersant and the pigment combination are subjected to the step of grinding the pigment as appropriate, and then the functionalized acid component is added to the pigment composition.

[0050] 39. The method of any one of Examples 36 to 38, wherein the polymeric dispersant comprises an average of 2 to 200 polyether side groups per molecule.

[0051] 40. The method of any one of Examples 36 to 39, wherein 50% to substantially all of the monomer units of the polyether side groups are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units.

[0052] 41. The method of any one of Examples 36 to 40, wherein the ratio of the number of poly(ethylene oxide) monomer units to the number of poly(propylene oxide) monomer units is from 0:100 to 90:10.

[0053] 42. The method of any one of Examples 36 to 41, wherein the polyether side groups account for at least 65% by weight of the polymer dispersant based on the total weight of the polymer dispersant.

[0054] 43. The method of any one of Examples 36 to 42, wherein the polymeric dispersant comprises an average of 2 to 500 amine groups per molecule.

[0055] 44. The method of any one of Examples 36 to 43, wherein the functionalized acid component comprises a sulfonic acid functionalized with at least one of aromatic or aliphatic functional groups.

[0056] 45. The method of any one of Examples 36 to 44, wherein the functionalized acid component comprises dodecylbenzenesulfonic acid.

[0057] 46. ​​The method of any one of Examples 36 to 45, wherein the aromatic functional group is, where appropriate, a substituted C6-C10 aromatic group.

[0058] 47. The method of any one of Examples 36 to 46, wherein the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C8-C22 hydrocarbon group.

[0059] 48. The method of any one of Examples 36 to 47, wherein the functionalized acid component comprises at least one compound according to the following general formula: Wherein: R1 is a straight-chain or branched-chain, saturated or unsaturated C8-C22 hydrocarbon group; R2 is an aromatic functional group, which may be a substituted C6-C10 aromatic group; W is phosphorus or sulfur; m is 1 or 2, where m is 1 or 2 when W is sulfur, and m is 1 when W is phosphorus; n is 1 or 2, where n is 1 when W is sulfur, and n is 2 when W is phosphorus; s is 0 or 1; t is 0 or 1; conditional s and t cannot both be 0.

[0060] 49. The method of Example 48, wherein W is sulfur.

[0061] 50. The method as in Example 48 or Example 49, wherein s is 1 and t is 1.

[0062] 51. The method of any one of Examples 36 to 50, wherein at least about 75% of the amine groups present in the polymeric dispersant are individually neutralized by the molecules of the functionalized acid component.

[0063] 52. The method of any one of Examples 36 to 59, wherein at least about 95% of the amine groups present in the polymeric dispersant are individually neutralized by the molecules of the functionalized acid component.

[0064] 53. A method for manufacturing an ink formulation, comprising: (a) performing the method of any one of Examples 36 to 52 to form a pigment dispersion; and (b) adding to the pigment dispersion the following components: (i) a solvent; (ii) a binder; and (iii) at least one additional additive.

[0065] 54. The method of Example 53, wherein the solvent is a polar solvent.

[0066] 55. The method of Example 53 or Example 54, wherein the adhesive is a polymer adhesive.

[0067] 56. The method of any one of Examples 53 to 55, wherein at least one additional additive comprises 1 to 5 additional additives.

[0068] 57. The method of any one of Examples 53 to 56, wherein the at least one additional additive comprises at least one of a wetting agent, a stabilizer, a tackifier, a wax, or a defoamer. Simple Explanation of the Diagram

[0069] none. Implementation

[0070] The various features and embodiments of the subject matter of this invention will be described below with the aid of a non-limiting description.

[0071] As used herein, the indefinite article "a / an" is intended to mean one or more. As used herein, the phrase "at least one" means one or more of the following terms. Therefore, "a / an" and "at least one" are used interchangeably. For example, in an alternative embodiment, "at least one of A, B, or C" means that it may include only one of A, B, or C, and may include any mixture of two or more of A, B, and C.

[0072] As used herein, the term "substantially" means that the value of a given quantity is within ±10% of a specified value. In other embodiments, the value is within ±5% of the specified value. In other embodiments, the value is within ±2.5% of the specified value. In other embodiments, the value is within ±1% of the specified value.

[0073] As used herein, the term "substantially free of" means that a component does not contain any material that is intentionally added to the component and is "substantially free of". For example, a component may contain material that is "substantially free of" in amounts not exceeding the impurity content of the material, which may be the result of incomplete chemical reactions and / or unintended / undesired (but possibly unavoidable) reaction products.

[0074] As used herein, the transitional term "comprising," "containing," or "characterized in" is inclusive or open-ended and does not exclude additional unlisted elements or method steps. However, in each enumeration of "comprising" herein, the term is also intended to cover the phrases "consistent with" and "composed of" as alternative embodiments, wherein "composed of" excludes any unspecified elements or steps, and "consistent with" permits the inclusion of additional unlisted elements or steps that do not materially affect the principal or essential and novel features of the composition or method under consideration.

[0075] A composition is provided comprising: (a) a polymeric dispersant comprising: (i) at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; and (ii) at least two amino groups per molecule, wherein the at least two amino groups are not present in the at least two polyether side groups; and (b) a functionalized acid component comprising sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; and wherein at least 60% of the amino groups present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component. When describing an acid component functionalized with at least one of aromatic or aliphatic functional groups herein, it means that the acid component is functionalized with an aromatic or aliphatic functional group, and, where applicable, any of these functional groups is further functionalized with another type of functional group. For example, an acid component may be functionalized with an aromatic functional group, and, where applicable, the aromatic functional group may be further functionalized with an aliphatic functional group, or vice versa.

[0076] As used herein, the term "one or more polyether side groups" refers to a polyether group attached to the main chain of a polymer dispersant. In some embodiments, one or more polyether side groups may be formed by joining multiple alkyl oxide monomer units (such as ethylene oxide and / or propylene oxide monomer units), possibly in combination with other monomer units, together by known methods to form a polyether group, and then attaching the polyether group to the main chain by known methods. This method of forming a polymer dispersant provides the simplest conceptual understanding of the meaning of the terms "one or more polyether side groups" and "main chain".

[0077] In some embodiments, one or more polyether side groups can be "grown" from the main chain of the polymer dispersant by adding alkyl oxide monomer units (such as ethylene oxide and / or propylene oxide monomer units) to the main chain, and then adding additional alkyl oxide monomer units (such as ethylene oxide and / or propylene oxide monomer units) sequentially to the first to form one or more side groups. (This method may produce polymer dispersants that are the same as or very similar to those formed in the methods described in the preceding paragraph.) In this case, the term "one or more polyether side groups" will be understood to mean a portion of the polymer dispersant that begins with the first alkyl oxide monomer unit attached to the main chain and continues via additional alkyl oxide monomer units attached to the first alkyl oxide monomer unit. The "main chain" will then be considered as the portion of the polymer dispersant that is not one or more polyether side groups.

[0078] In any of the methods described in the preceding two paragraphs, one or more polyether side groups will be capped with monomer units that remain relatively unreactive compared to the monomer units constituting the majority of the one or more polyether side groups, as is well known in the art. In some embodiments, substantially all monomer units of one or more polyether side groups may be alkylene oxide monomer units (such as ethylene oxide and / or propylene oxide monomer units). “Substantially all” means that: (i) all monomer units of one or more polyether side groups, except for the capping monomer units, are alkylene oxide monomer units; and / or (ii) a small number of monomer units may not be alkylene oxide monomer units because of unintentional impurities in the monomer units used to form one or more polyether side groups.

[0079] As used herein, the terms "poly(epoxide) monomer unit" and "epoxide monomer unit" are used interchangeably. Similarly, the terms "poly(ethylene oxide) monomer unit" and "ethylene oxide monomer unit" are used interchangeably, and the terms "poly(propylene oxide) monomer unit" and "propylene oxide monomer unit" are used interchangeably. All such terms refer to individual monomer units joined together (directly or indirectly) to form one or more polyether side groups as described herein.

[0080] In some embodiments, the polymeric dispersant comprises an average of 2 (such as 3, 4, 5, 6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 25, 30, 35, 40, 45, 50 or 55) to 200 (e.g. 190, 180, 170, 160, 150, 140, 130, 120, 110, 100, 95, 90, 85, 80, 75, 70, 65 or 60) polyether side groups per molecule. In some embodiments, the polymeric dispersant comprises an average of 2 (such as 3, 4, 5, 6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95 or 100) to 200 (such as 190, 180, 170, 160, 150, 140, 130, 120 or 110) polyether side groups per molecule.

[0081] In some embodiments, 50% to substantially all of the monomer units in the polyether side group are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, substantially all of the monomer units in the polyether side group are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, 50% (such as 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or 95%) to 99% of the monomer units in the polyether side group are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, 50% (such as 55%, 60%, 65%, 70%, 75%, 80%, 85%, or 90%) to 95% of the monomer units in the polyether side group are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, 50% (such as 55%, 60%, 65%, 70%, 75%, 80%, or 85%) to 90% of the monomer units in the polyether side groups are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, 50% (such as 55%, 60%, 65%, 70%, 75%, or 80%) to 85% of the monomer units in the polyether side groups are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, 50% (such as 55%, 60%, 65%, 70%, or 75%) to 80% of the monomer units in the polyether side groups are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, 50% (such as 55%, 60%, 65%, or 70%) to 75% of the monomer units in the polyether side groups are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, 50% (e.g., 55%, 60%, or 65%) to 70% of the monomer units in the polyether side group are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, 50% (e.g., 55% or 60%) to 65% of the monomer units in the polyether side group are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units. In some embodiments, 50% to 55% of the monomer units in the polyether side group are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units.

[0082] In some embodiments, the ratio of the number of poly(ethylene oxide) monomer units to the number of poly(propylene oxide) monomer units is from 0:100 (such as 10:90 or 20:80) to 100:0 (such as 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, or 30:70). In some embodiments, the ratio of the number of poly(ethylene oxide) monomer units to the number of poly(propylene oxide) monomer units is 0:100, 10:90, 17:83, 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10, or 100:0.

[0083] In some embodiments, the polyether side groups account for at least 65% (such as 70, 75, 80, 85, 90, or 95) by weight of the polymer dispersant, based on the total weight of the polymer dispersant. In some embodiments, the polyether side groups account for 65% to 95% (such as 70, 75, 80, 85, or 90) by weight of the polymer dispersant, based on the total weight of the polymer dispersant. In some embodiments, the polyether side groups account for 65% to 85% (such as 70, 75, 80, or 85) by weight of the polymer dispersant, based on the total weight of the polymer dispersant. In some embodiments, the polyether side groups account for 65% to 80% (such as 70 or 75) by weight of the polymer dispersant, based on the total weight of the polymer dispersant. In some embodiments, the polyether side groups account for 65 (such as 70) to 75% by weight of the polymer dispersant based on the total weight of the polymer dispersant. In some embodiments, the polyether side groups account for 65 to 70% by weight of the polymer dispersant based on the total weight of the polymer dispersant. In some embodiments, the polyether side groups account for 65 (such as 70, 75, 80, 85, 90, or 95)% by weight of the polymer dispersant based on the total weight of the polymer dispersant.

[0084] In some embodiments, the polymeric dispersant comprises an average of 2 per molecule (such as 3, 4, 5, 6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 110, 120, 130, 140, 150, 160, 170, 18). 0, 190, 200, 210, 220, 230 or 240) to 500 (such as 490, 480, 470, 460, 450, 440, 430, 420, 410, 400, 390, 380, 370, 360, 350, 340, 330, 320, 310, 300, 290, 280, 270, 260 or 250) amino groups. In some embodiments, the polymeric dispersant comprises an average of 2 per molecule (such as 3, 4, 5, 6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 110, 120, 130, 140, 150, 160, 170, 18). 0 or 190) to 500 (such as 490, 480, 470, 460, 450, 440, 430, 420, 410, 400, 390, 380, 370, 360, 350, 340, 330, 320, 310, 300, 290, 280, 270, 260, 250, 240, 230, 220, 210 or 200) amino groups. In some embodiments, the polymeric dispersant comprises an average of 2 per molecule (such as 3, 4, 5, 6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 110, 120, 130, 140, 150, 160, 170, 18). 0, 190, 200, 210, 220, 230, 240, 250, 260, 270, 280 or 290) to 500 (such as 490, 480, 470, 460, 450, 440, 430, 420, 410, 400, 390, 380, 370, 360, 350, 340, 330, 320, 310 or 300) amino groups.

[0085] In some embodiments, the functionalized acid component includes a sulfonic acid functionalized with at least one of aromatic or aliphatic functional groups.

[0086] In some embodiments, the functionalized acid component includes dodecylbenzenesulfonic acid. An exemplary commercially available dodecylbenzenesulfonic acid system is Maranil® DBS / LC, which is available from BASF.

[0087] In some embodiments, the aromatic functional group is a substituted C6-C10 aromatic group, as appropriate. In some embodiments, the aromatic functional group is a C6-C10 aromatic group. In some embodiments, the aromatic functional group is a substituted C6-C10 aromatic group. In some embodiments, the aromatic functional group is a substituted C8-C10 aromatic group, as appropriate. In some embodiments, the aromatic functional group is a C8-C10 aromatic group. In some embodiments, the aromatic functional group is a substituted C8-C10 aromatic group. In some embodiments, the aromatic functional group is a substituted C6-C8 aromatic group, as appropriate. In some embodiments, the aromatic functional group is a C6-C8 aromatic group. In some embodiments, the aromatic functional group is a substituted C6-C8 aromatic group, as appropriate. In some embodiments, the aromatic functional group is a C6 aromatic group. In some embodiments, the aromatic functional group is a substituted C6 aromatic group. In some embodiments, the aromatic functional group is, as appropriate, a substituted C8 aromatic group. In some embodiments, the aromatic functional group is a C8 aromatic group. In some embodiments, the aromatic functional group is a substituted C8 aromatic group. In some embodiments, the aromatic functional group is, as appropriate, a substituted C10 aromatic group. In some embodiments, the aromatic functional group is a C10 aromatic group. In some embodiments, the aromatic functional group is a substituted C10 aromatic group.

[0088] In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C8-C22 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C8-C20 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C8-C18 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C8-C16 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C8-C14 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C8-C12 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C8-C10 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C8 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C10-C22 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C10-C20 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C10-C18 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C10-C16 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C10-C14 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C10-C12 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C10 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C12-C22 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C12-C20 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C12-C18 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C12-C16 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C12 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C14-C22 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C14-C20 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C14-C18 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C14-C16 hydrocarbon group.In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C14 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C16-C22 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C16-C20 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C16 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C18-C22 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C18-C20 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched, saturated or unsaturated C18 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C20-C22 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C20 hydrocarbon group. In some embodiments, the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C22 hydrocarbon group.

[0089] In some embodiments, the functionalized acid component comprises at least one compound according to the following general formula: in: R1 is a straight-chain or branched-chain, saturated or unsaturated C8-C22 hydrocarbon group (in alternative embodiments, R1 may be a hydrocarbon group of one of the various embodiments described above); R2 is an aromatic functional group, which may be a substituted C6-C10 aromatic group (in alternative embodiments, R2 may be an aromatic group of one of the above-described embodiments); W-series phosphorus or sulfur; m series 1 or 2, where m series 1 or 2 is sulfur and m series 1 is phosphorus; n-series 1 or 2, where n-series 1 is sulfur and n-series 2 is phosphorus; s is either 0 or 1; t is either 0 or 1; The conditional coefficients s and t cannot both be 0.

[0090] In some embodiments, W-based sulfur. In some embodiments, W-based phosphorus. In some embodiments, W-based sulfur, m-based 1, and n-based 1. In some embodiments, W-based sulfur, m-based 2, and n-based 1. In some embodiments, W-based phosphorus, m-based 1, and n-based 2.

[0091] In some embodiments, s is 1 and t is 1. In some embodiments, s is 0 and t is 1. In some embodiments, s is 1 and t is 0.

[0092] In some embodiments, at least 60% (e.g., 65, 70, 75, 80, 85, 90, or 95)% of the amines present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component. In some embodiments, substantially all the amines present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component. In this context, "substantially all" means that the number of amines neutralized by a molecule of the functionalized acid component in this case is as physically / chemically high as possible.

[0093] As is present in polymeric dispersants, each amine group can be independently a primary, secondary, or tertiary amine group. In some embodiments, the amine groups present in the polyether side groups may not be desirable, as they may cause the polyether side groups to associate more readily with the pigment surface rather than to solvate in the liquid medium, or otherwise make the polyether side groups unsuitable for their purpose of dispersing pigments (linked to one or more amine groups of the main chain) into the liquid medium.

[0094] Suitable polymeric dispersants according to this subject matter are disclosed, for example, in US 7,767,750 B2, US 8,859,675 B2, US 8,987,374 B2, and US 9,416,280 B2. Note that these documents may disclose polymeric dispersants beyond the most extensive scope of this subject matter; it is cautioned that these documents disclose examples of many suitable polymeric dispersants that fall within the scope of this subject matter and are therefore illustrative of the polymeric dispersants described herein.

[0095] In some embodiments, the above-described one or more components do not contain materials that could interfere with the neutralization of amine groups by the functionalized acid component. In some embodiments, materials that might interfere with the neutralization of amine groups by the functionalized acid component are added to the one or more components described herein only after the desired amount of neutralization has occurred.

[0096] Also provided is a pigment dispersion comprising: (a) a pigment; and (b) a polymeric dispersant for the pigment, the polymeric dispersant comprising: (i) at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; and (ii) at least two amine groups per molecule, wherein the at least two amine groups are not present in the at least two polyether side groups; and (c) a functionalized acid component comprising sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; and wherein at least 60% of the amine groups present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component. In some embodiments, one or more pigment dispersions include: (a) a pigment; and (b) any of the above-described components.

[0097] Further provided are ink formulations comprising: (a) one or more pigment dispersions described above; (b) a solvent; (c) a binder; and (d) at least one additional additive.

[0098] In some embodiments, the solvent is a polar solvent.

[0099] In some embodiments, the adhesive is a polymer adhesive.

[0100] In some embodiments, the at least one additional additive includes 1 to 5 additional additives.

[0101] In some embodiments, the at least one additional additive includes at least one of a wetting agent, a stabilizer, a tackifier, a wax, or a defoamer.

[0102] In some embodiments, materials that may interfere with the neutralization of amine groups by functionalized acid components may not be added to one or more ink formulations described herein until the desired amount of neutralization has occurred.

[0103] A method for producing a pigment dispersion is also provided, comprising the steps of combining a pigment, a polymeric dispersant for the pigment, and a functionalized acid component in any order, and the step of grinding the pigment as appropriate, wherein: (a) the polymeric dispersant comprises: (i) at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; (ii) at least (a) two amine groups, wherein the at least two amine groups are not present in the at least two polyether side groups; (b) the functionalized acid component comprises sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; (c) at least 60% of the amine groups present in the polymer dispersant are individually neutralized by the molecules of the functionalized acid component; and (d) the step of grinding the pigment as appropriate: (i) not performed; (ii) performed on the pigment alone before the addition of the polymer dispersant and / or the functionalized acid component; or (iii) performed on a combination of the pigment and the polymer dispersant and / or the functionalized acid component.

[0104] In some embodiments, the polymeric dispersant and the functionalized acid component are combined before the pigment is added, wherein the step of grinding the pigment, as appropriate, is performed before or after the pigment is added to the combination of the polymeric dispersant and the functionalized acid component. In some embodiments, the polymeric dispersant and the functionalized acid component are combined before the pigment is added, wherein the step of grinding the pigment is performed before or after the pigment is added to the combination of the polymeric dispersant and the functionalized acid component. In some embodiments, the polymeric dispersant and the functionalized acid component are combined before the pigment is added, wherein the step of grinding the pigment is performed after the pigment is added to the combination of the polymeric dispersant and the functionalized acid component.

[0105] In some embodiments, the polymer dispersant and the pigment are combined, the combination of the polymer dispersant and the pigment is subjected to a grinding step of the pigment as appropriate, and then the functionalized acid component is added to the pigment composition. In some embodiments, the polymer dispersant and the pigment are combined, the combination of the polymer dispersant and the pigment is subjected to a grinding step of the pigment, and then the functionalized acid component is added to the pigment composition.

[0106] In some embodiments, the polymeric dispersant for the pigment and the functionalized acid component may together be composed of any of the components described above.

[0107] A method for manufacturing an ink formulation is further provided, comprising: (a) performing one or more methods described above to manufacture a pigment dispersion to form a pigment dispersion; and (b) adding the following components to the pigment dispersion: (i) a solvent; (ii) a binder; and (iii) at least one additional additive.

[0108] In some embodiments, the solvent is a polar solvent.

[0109] In some embodiments, the adhesive is a polymer adhesive.

[0110] In some embodiments, the at least one additional additive includes 1 to 5 additional additives.

[0111] In some embodiments, the at least one additional additive includes at least one of a wetting agent, a stabilizer, a tackifier, a wax, or a defoamer.

[0112] In some embodiments of the methods described above, materials that may interfere with the neutralization of amine groups by functionalized acid components may not be added to one or more ink formulations described herein until the desired amount of neutralization has occurred. These materials may comprise resins, binders, and / or additional additives, as will be apparent to those skilled in the art.

[0113] The topics revealed in this article can be better understood by referring to the following examples, which are merely illustrative and further illustrate the topics revealed herein. These illustrative examples should not be construed as limiting the topics in any way.

[0114] Comparative Example 1: Example 1 from column 11, lines 35-57 of US 7,767,750 B2, granted to inventor Dean Thetford and assignee The Lubrizol Corporation on August 3, 2010.

[0115] Comparative Example 2: Intermediate A was prepared as follows: 200 parts of SURFONAMINE® B-200 polyetheramine (from Huntsman International LLC), 11.6 parts of 2-hydroxyethyl acrylate, and 0.03 parts of 2,6-di-tert-butyl-4-methylphenol were loaded into a reaction vessel and stirred at 70°C for 48 hours. Under nitrogen atmosphere, 250 parts of ethyl acetate and 67.6 parts of toluene-2,4-diisocyanate were loaded into another reaction vessel, followed by stirring and, after 10 minutes, 289.7 parts of intermediate A and 125 parts of ethyl acetate were loaded. Then, after 10 minutes, 15.78 parts of 1,1'-((3-(dimethylamino)propyl)imino)bis(2-propanol) and 32.55 parts of ethyl acetate were loaded into the vessel. The mixture was then heated to 65°C and held for one hour. Next, 95.13 parts of SURFONAMINE® B-200 polyetheramine and 94.7 parts of ethyl acetate were added, and the mixture was stirred at 65°C for another two hours to obtain the dispersant of Comparative Example 2.

[0116] Comparative Example 3: A dispersant was prepared using 24 parts EF60, 50 parts Jeffamine M2005, and 0.93 parts ethyl acetate containing DMAPA, according to the method described in Example 7, column 11, lines 45-53, of US 9,416,280 B2, granted to inventors Stuart N. Richards and assignee Lubrizol Limited on August 16, 2016 (see Comparative Example C, column 10, lines 25-48). The resulting mixture was adjusted to 40.0% by weight of solids by adding additional ethyl acetate.

[0117] Comparative Example 4: The dispersant was prepared by adding 0.25 parts of acetic acid to 1.75 parts of Comparative Example 1, followed by mechanical stirring for about 1 minute until the material appeared uniform, and then placing the container on a set of rollers for gentle mixing for about 30 minutes.

[0118] Comparative Example 5: The dispersant was made by adding 0.13 parts of benzoic acid to 1.87 parts of Comparative Example 1, followed by mechanical stirring for about 1 minute until the material appeared uniform, and then placing the container on a set of rollers for gentle mixing for about 30 minutes.

[0119] Example 1: A mixture of 225 parts of Comparative Example 1 and 309.38 parts of ethanol was stirred at 50°C for 1 hour, followed by the addition of 84.38 parts of dodecylbenzenesulfonic acid and stirring at 50°C for another hour to form a dispersant.

[0120] Example 2: A mixture of 6.15 parts of Comparative Example 2 and 22.48 parts of ethanol was mechanically stirred for about 1 minute until the material appeared homogeneous. The container was then placed on a set of rollers and gently mixed for about 30 minutes. Then, 0.47 parts of dodecylbenzenesulfonic acid was added to the mixture, followed by mechanical stirring for about 1 minute until the material appeared homogeneous. The container was then placed on a set of rollers and gently mixed for about 30 minutes to form a dispersant.

[0121] Example 3: A mixture of 7.14 parts of Comparative Example 3, 19.52 parts of ethanol, and 2.17 parts of ethyl acetate was mechanically stirred for about 1 minute until the material appeared homogeneous. The container was then placed on a set of rollers and gently mixed for about 30 minutes. Next, 0.47 parts of dodecylbenzenesulfonic acid were added to the mixture, followed by mechanical stirring for about 1 minute until the material appeared homogeneous. The container was then placed on a set of rollers and gently mixed for about 30 minutes to form a dispersant.

[0122] Example 4: 35 parts of Comparative Example 3 were loaded into a reaction flask and stirred under nitrogen. 0.21 parts of benzenesulfonic acid and 0.21 parts of ethyl acetate were added to the reaction vessel. The reaction mixture was then heated to 50°C and maintained for 1 hour. A condenser was installed on the flask to form a dispersant.

[0123] Example 5: 35 parts of Comparative Example 3 were loaded into a reaction flask and stirred under nitrogen. 0.21 parts of phenylphosphonic acid and 0.21 parts of ethyl acetate were loaded into the reaction vessel. The reaction mixture was then heated to 50°C and maintained for 1 hour. A condenser was installed on the flask to form a dispersant.

[0124] To determine whether a particular dispersant is suitable for inks (such as those used in printed packaging materials), two types of tests can be performed: compatibility tests and one or both of dispersion tests A and B, as described below. If a particular dispersant passes at least one of the compatibility tests and dispersion test A or dispersion test B, it can be considered suitable for (packaging) inks.

[0125] Each dispersant described in the above examples and comparative examples was tested according to one of the compatibility test and dispersion test A or dispersion test B, and the results are reported in Table 1 below. The compatibility test is a measure of whether a dispersant is compatible with the ink medium. Dispersion tests A and B are methods for determining whether a dispersant can disperse a particular pigment, and each test represents whether other similar pigments can pass the same test, thus indicating that the dispersant is suitable for use with other similar pigments. Therefore, passing at least one of the compatibility test and dispersion test A or dispersion test B indicates that the particular dispersant is suitable for use with at least one type of pigment.

[0126] Compatibility Test (“CT”): Four parts of nitrocellulose varnish (DLX3-5 from Nobel NC Co., Ltd.) were dissolved in five parts of ethanol and one part of ethyl acetate to prepare a varnish solution. Separately, two parts of dispersant were dissolved in three parts of ethanol. Five parts of the varnish solution were added to the mixture and stirred, followed by the addition of two parts of an organotitanate (IAM from Dorf Ketal Chemicals India Pvt Ltd) and stirring until homogeneous. After storage at room temperature for two weeks, the mixture was observed, and any gel formation and / or turbidity was recorded as failing the compatibility test, while a flowable, clear fluid was recorded as passing the compatibility test.

[0127] Dispersion Test B (“DTB”): Dissolve 3.39 parts of dispersant in 22.48 parts of ethanol and 3.39 parts of ethyl acetate. Add 15.75 parts of pigment blue 15:4 and stir to wet the pigment. Add 125 parts of 3 mm glass beads and disperse the resulting mixture for one hour using a DAS 200 disperser (available from LAU GmbH) to produce a grinding matrix. Measure the viscosity of the grinding matrix using a TA rheometer at 25°C and a 250 µm gap using a parallel plate setup. Viscosities equal to or greater than 2 Pa·s at a shear rate of 38 s⁻¹ are considered unacceptable in Dispersion Test B, while values ​​below 2 Pa·s at a shear rate of 38 s⁻¹ are considered acceptable in Dispersion Test B. Table 1 CT DTA DTB overall Comparison Example 1 Gelation - Unqualified 0.26 Pa·s - Qualified Unqualified Example 1 Fluid - Qualified 0.99 Pa·s - Qualified qualified Comparison Example 2 Gelation - Unqualified 0.08 Pa·s - Qualified Unqualified Example 2 Fluid - Qualified 0.39 Pa·s - Qualified qualified Comparison Example 3 Gelation - Unqualified 0.07 Pa·s - Qualified Unqualified Example 3 Fluid - Qualified 1.06 Pa·s - Qualified qualified Comparison Example 4 Gelation - Unqualified 2.09 Pa·s - Unacceptable Unqualified Comparison Example 5 Gelation - Unqualified 2.77 Pa·s - Unacceptable Unqualified Example 4 Fluid - Qualified 0.65 Pa·s - Qualified qualified Example 5 Fluid - Qualified 0.22 Pa·s - Qualified qualified

[0128] Unless explicitly indicated or required in the examples or context, all quantities of materials, reaction conditions, molecular weights, number of carbon atoms, and similar quantities specified in this specification shall be understood to be modified by the word “about.” As used herein, the term “about” means that the value of a given quantity is within ±20% of a specified value. In other embodiments, the value is within ±15% of a specified value. In other embodiments, the value is within ±10% of a specified value. In other embodiments, the value is within ±5% of a specified value. In other embodiments, the value is within ±2.5% of a specified value. In other embodiments, the value is within ±1% of a specified value. In other embodiments, based on the disclosure provided herein, the value is within the range of explicitly described values ​​as understood by those skilled in the art, performing in a manner substantially similar to a composition including the literal quantities described herein.

[0129] It should be understood that the higher and lower quantities, ranges, and ratio limits described herein can be combined independently and cover any quantity within the disclosed range to provide a minimum or maximum value within a narrower range in alternative embodiments (the limitation of which is, of course, that the minimum quantity within the range must be lower than the maximum quantity within the same range). Similarly, the range and quantity of each element of the subject matter disclosed herein can be used in conjunction with the range or quantity of any of the other elements.

[0130] Although certain representative embodiments and details have been shown for the purpose of illustrating the subject matter disclosed herein, it will be apparent to those skilled in the art that various changes and modifications can be made therein without departing from the scope of the subject matter. In this regard, the scope of the invention is limited only by the following claims.

[0131] none

Claims

1. A composition comprising: a. A polymeric dispersant comprising: i. at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymeric dispersant based on the total weight of the polymeric dispersant; and ii. at least two amine groups per molecule, wherein the at least two amine groups are not present in the at least two polyether side groups; and b. a functionalized acid component comprising sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; and wherein at least 60% of the amine groups present in the polymeric dispersant are individually neutralized by a molecule of the functionalized acid component.

2. The composition of claim 1, wherein the polymeric dispersant comprises an average of 2 to 200 polyether side groups per molecule.

3. A composition as claimed in claim 1 or 2, wherein 50% to substantially all of the monomer units of the polyether side groups are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units.

4. The composition of claim 1 or 2, wherein the ratio of the number of poly(ethylene oxide) monomer units to the number of poly(propylene oxide) monomer units is from 0:100 to 90:

10.

5. A composition as claimed in claim 1 or 2, wherein the polyether side groups comprise at least 65% by weight of the polymer dispersant based on the total weight of the polymer dispersant.

6. A composition as claimed in claim 1 or 2, wherein the polymeric dispersant comprises an average of 2 to 500 amine groups per molecule.

7. The composition of claim 1 or 2, wherein the functionalized acid component comprises a sulfonic acid functionalized with at least one of an aromatic functional group or an aliphatic functional group.

8. A composition as claimed in claim 1 or 2, wherein the functionalized acid component comprises dodecylbenzenesulfonic acid.

9. A composition as claimed in claim 1 or 2, wherein the aromatic functional group is, where appropriate, a substituted C6-C10 aromatic group.

10. A composition of claim 1 or 2, wherein the aliphatic functional group is a straight-chain or branched-chain, saturated or unsaturated C8-C22 hydrocarbon group.

11. A composition as claimed in claim 1 or 2, wherein the functionalized acid component comprises at least one compound according to the following general formula: Wherein: R1 is a straight-chain or branched-chain, saturated or unsaturated C8-C22 hydrocarbon group; R2 is an aromatic functional group, which may be a substituted C6-C10 aromatic group; W is phosphorus or sulfur; m is 1 or 2, where m is 1 or 2 when W is sulfur and 1 when W is phosphorus; n is 1 or 2, where n is 1 when W is sulfur and 2 when W is phosphorus; s is 0 or 1; t is 0 or 1; conditional s and t cannot both be 0.

12. The composition of claim 11, wherein W is sulfur.

13. As in claim 11, wherein s is 1 and t is 1.

14. A composition as claimed in claim 1 or 2, wherein at least about 75% of the amine groups present in the polymeric dispersant are individually neutralized by the molecules of the functionalized acid component.

15. A composition of claim 1 or 2, wherein at least about 95% of the amine groups present in the polymeric dispersant are individually neutralized by the molecules of the functionalized acid component.

16. A pigment dispersion comprising: a. Pigment; and b. A polymeric dispersant for the pigment, the polymeric dispersant comprising any one of claims 1 to 15.

17. An ink formulation comprising: a. a pigment dispersion as claimed in claim 16; b. a solvent; c. a binder; and d. at least one additional additive.

18. A method for producing a pigment dispersion, comprising the steps of combining a pigment, a polymeric dispersant for the pigment, and a functionalized acid component in any order, and, as appropriate, the step of grinding the pigment, wherein: a. The polymer dispersant comprises: i. at least two polyether side groups per molecule, wherein the at least two polyether side groups are composed of monomer units, wherein at least half of the monomer units are poly(ethylene oxide) monomer units and / or poly(propylene oxide) monomer units, and wherein the at least two polyether side groups account for at least 50% by weight of the polymer dispersant based on the total weight of the polymer dispersant; ii. at least two amine groups per molecule, wherein the at least two amine groups are not present in the at least two polyether side groups; b. The functionalized acid component comprises sulfonic acid and / or phosphoric acid functionalized with at least one of aromatic or aliphatic functional groups; c. at least 60% of the amine groups present in the polymer dispersant are individually neutralized by a molecule of the functionalized acid component; and d. a step of grinding the pigment, as appropriate: i. not performed; ii. the pigment is ground separately before the addition of the polymer dispersant and / or the functionalized acid component; or iii. The combination of the pigment, the polymer dispersant, and / or the functionalized acid component is carried out.

19. The method of claim 18, wherein the polymeric dispersant and the functionalized acid component are combined before the pigment is added, wherein the step of grinding the pigment, as appropriate, is performed before or after the pigment is added to the combination of the polymeric dispersant and the functionalized acid component.

20. The method of claim 18, wherein the polymer dispersant and the pigment combination are subjected to the step of grinding the polymer dispersant and the pigment combination as appropriate, and then the functionalized acid component is added to the pigment composition.