AND METHODS FOR MAKING AND USING SAME

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to U.S. Provisional Patent Application No. 62/140,519, filed on March 31, 2015, U.S. Provisional Patent Application No. 62/140,523, filed on March 31, 2015, and U.S. Provisional Patent Application No. 62/140,518, filed on March 31, 2015, all of which are incorporated by reference herein.

BACKGROUND

Field

[0002] Embodiments described generally relate to wax compositions and methods for making and using same. More particularly, such embodiments relate to wax compositions that include a base wax and a rosin oil and methods for making and using same.

Description of the Related Art

[0003] Wax and gel compositions of a transparent or translucent nature are used in a variety of commercial applications. Many wax and gel compositions also include the addition of a solvent to provide the overall composition with specified and desired properties. For example, the addition of a solvent can impart various textures on the surface of the wax or gel composition, provide a desired viscosity, and/or provide a desired melting point for the composition.

[0004] Typical solvents added to wax and gel compositions include mineral oils, silicone oils, vegetable oils, e.g., castor oil, long-chain alkyl esters, e.g., iso-propyl isostearate, and terpenes, e.g., limonene. Depending on the particular commercial application for a given wax composition, however, many of these solvent may not be desirable or compatible.

[0005] There is a need, therefore, for improved wax compositions and methods for making and using same.

SUMMARY

[0006] Wax compositions that include a base wax and a rosin oil and methods for making and using same are provided. In some examples, the wax composition can include a base wax and a rosin oil. The rosin oil can include a decarboxylated rosin acid and less than 25 wt% of rosin acids. The wax composition can include about 5 wt% to about 80 wt% of the rosin oil, based on a combined weight of the base wax and the rosin oil.

[0007] In some examples, the wax composition can include a base wax and a rosin oil. The base wax can be or include a reaction product of dimerized tall oil fatty acids and an amine. The amine can be or include ethylamine, ethylenediamine, propylamine, propylenediamine, laurylamine, octadecylamine, or any mixture thereof. The rosin oil can include decarboxylated tall oil rosin acids and less than 25 wt% of rosin acids. The wax composition can include about 5 wt% to about 80 wt% of the rosin oil, based on a combined weight of the base wax and the rosin oil.

[0008] In some examples, a method for making a wax composition can include combining a first catalyst and a mixture that can include fatty acids and rosin acids to produce a first mixture. The mixture includes fatty acids and rosin acids can have a first dehydroabietic acid concentration. The first mixture can be heated to a first temperature that is less than 250°C to produce a first reaction mixture that can have a second dehydroabietic acid concentration greater than the first dehydroabietic acid concentration. The first reaction mixture can be heated to a second temperature that is at 250°C or more to produce a second reaction mixture. The second reaction mixture can include rosin oil, dimer acids, and monomer acids, and can have a rosin oil yield of greater than 25%. A reagent can be combined with the second reaction mixture to produce a third mixture. The reagent can be or include an amine, an alcohol, or a mixture thereof. The third mixture can be heated to a temperature of about 80°C to about 300°C to produce a base wax. The third mixture that includes the base wax and the rosin oil can be cooled to a temperature of about 20°C to about 30°C to produce a wax composition. The wax composition can include about 5 wt% to about 80 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil.

DETAILED DESCRIPTION

[0009] The wax composition can include one or more base waxes and one or more rosin oils. Ion one example, the base wax can be or include one or more reaction products derived or made from reacting together one or more dimer fatty acids and one or more reagents. The reagent can be or include one or more amines, one or more alcohols, or any mixture thereof. In another example, the base wax can be or include one or more amides or polyamides, e.g., diamides and/or triamides. The rosin oil can be made from tall oil rosin acids and/or other rosin acids sources. For example, at least a portion of the rosin acids in the tall oil rosin acids and/or other rosin acids sources can be decarboxylated with heat and/or contact with one or more catalysts to produce or otherwise form the rosin oil. The rosin oil can include less than 25 wt% of rosin acids. The rosin oil can also have an acid value of less than 150 mg KOH/g of the rosin oil, as measured according to ASTM D465-15. The base wax and the rosin oil can provide a wax composition having one or more desired properties.

[0010] The wax composition can include about 5 wt% to about 95 wt% of the base wax, based on the total or combined weight of the base wax and the rosin oil. For example, the wax composition can include about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 30 wt%, or about 40 wt% to about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt% of the base wax, based on the combined weight of the base wax and the rosin oil.

[0011] The wax composition can include about 5 wt% to about 95 wt% of the rosin oil, based on the total or combined weight of the base wax and the rosin oil. For example, the wax composition can include about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 30 wt%, or about 40 wt% to about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil.

[0012] In one example, the wax composition can include about 80 wt% to about 95 wt% or about 80 wt% to about 90 wt% of the base wax and about 5 wt% to about 20 wt% or about 10 wt% to about 20 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil. In another example, the wax composition can include about 50 wt% to about 80 wt% of the base wax and about 20 wt% to about 50 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil. In another example, the wax composition can include about 30 wt% to about 50 wt% of the base wax and about 50 wt% to about 70 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil. In another example, the wax composition can include about 10 wt% to about 30 wt% of the base wax and about 70 wt% to about 90 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil. In another example, the wax composition can include greater than 25 wt% to about 95 wt% of the base wax and less than 75 wt% to about 5 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil.

[0013] The wax composition and can have a viscosity of about 1,000 pascal-second (Pa-s) to about 28,000 Pa-s at a temperature of about 25°C. For example, the wax composition can have a viscosity of about 1,000 Pa-s, about 2,000 Pa-s, about 3,000 Pa-s, about 4,000 Pa-s, about 5,000 Pa-s, about 6,000 Pa-s, about 7,000 Pa-s, about 8,000 Pa-s, about 9,000 Pa-s, about 10,000 Pa-s, about 12,000 Pa-s, or about 13,000 Pa-s to about 18,000 Pa-s, about 20,000 Pa-s, about 22,000 Pa-s, about 24, 000 Pa-s, about 26,000 Pa-s, or about 28,000 Pa-s at a temperature of about 25°C. The viscosity of the wax composition can be measured by a cone and plate rheometer as a function of temperature or at a desired temperature at a shear rate of about 1 Hz. The viscosity of the wax composition can generally be less than the viscosity of the base wax. For example, the wax composition can have a viscosity of about 10% to about 90% of a viscosity of the base wax at a temperature of about 25°C.

[0014] The wax composition can have a weight ratio of the base wax to the rosin oil of about 1 :9 to about 9: 1. For example, the wax composition can have a weight ration of the base wax to the rosin oil of about 1 :9, about 1 :8, about 1 :7, about 1 :6, about 1 :5, about 1 :4, about 1 :3, about 1 :2, or about 1 : 1 to about 2: 1, about 3 : 1, about 4: 1, about 5: 1, about 6: 1, about 7: 1, about 8: 1, or about 9: 1.

[0015] The rosin oil can be or include one or more decarboxylated rosin acids. The rosin acid that can be decarboxylated to produce the rosin oil can be derived, formed, or otherwise produced, at least in part, from one or more rosin acids or rosin acid sources. The one or more rosin acids or rosin acid sources can be decarboxylated with heat and/or contacted with one or more catalysts to produce or otherwise form the rosin oil. The catalyst can be used to improve the rate of decarboxylation of the rosin acids, such as to accelerate the loss of rosin carboxylic acid groups, and/or to decrease reaction temperatures. Illustrative decarboxylation catalysts can be or include, but are not limited to, sulfuric acid, phosphoric acid, diphenyl sulfide, benzyl phenyl sulfide, ditolyl sulfide, dinaphthyl sulfide, diheptyl sulfide, sodium sulfide, potassium sulfide, lithium sulfide, magnesium sulfide, calcium sulfide, iron sulfide, or any mixture thereof. Processes that can be used to produce the rosin oils from rosin acids can include those discussed and described in U.S. Patent No. 4,515,713. [0016] The rosin acids can be heated to form, make, or otherwise produce the rosin oils at a temperature of about 50°C, about 60°C, about 70°C, about 80°C, about 90°C, about 100°C, about 110°C, about 120°C, about 130°C, about 140°C, about 150°C, about 160°C, about 170°C, about 180°C, about 190°C, about 200°C, or about 250°C to about 300°C, about 310°C, about 320°C, about 330°C, about 340°C, about 350°C, about 360°C, about 370°C, about 380°C, about 390°C, about 400°C, about 410°C, about 420°C, about 430°C, about 440°C, about 450°C, about 460°C, about 470°C, about 480°C, about 490°C, or about 500°C. The rosin acids can be heated for about 0.5 hr to about 24 hr, about 1 hr to about 24 hr, about 1 hr to about 12 hr, about 2 hr to about 12 hr, about 2 hr to about 6 hr, about 2 hr to about 5 hr, or about 2 hr to about 4 hr to form the rosin oils.

[0017] The rosin oil can include rosin acids in an amount of less than 60 wt%, less than 50 wt%, less than 40 wt%, less than 30 wt%, less than 25 wt%, less than 23 wt%, less than 20 wt%, less than 17 wt%, less than 15 wt%, less than 10 wt%, less than 7 wt%, less than 5 wt%, less than 3 wt%, or less than 1 wt%. For example, the rosin oil can include rosin acids in an amount of about 0.01 wt% to less than 15 wt%, about 0.01 wt% to less than 10 wt%, about 0.01 wt% to less than 5 wt%, about 1 wt% to less than 15 wt%, or about 0.01 wt% to less than 25 wt%. In at least one example, the wax composition can include less than less than 25 wt%, less than 23 wt%, less than 20 wt%, less than 17 wt%, less than 15 wt%, less than 10 wt%, less than 7 wt%, less than 5 wt%, less than 3 wt%, or less than 1 wt% or rosin acids, based on the combined weight of the base wax and the rosin oil. For example, the wax composition can include rosin acids in an amount of about 0.01 wt%, about 0.1 wt%, about 0.5 wt%, about 1 wt%, or about 3 wt% to less than 10 wt%, less than 15 wt%, less than 20 wt%, or less than 25 wt%, based on the combined weight of the base wax and the rosin oil.

[0018] The rosin oil can have an acid value of about 1, about 20, about 30, or about 50 to about 60, about 80, about 100, about 120, about 140, or about 150 mg KOH/g of rosin oil, as measured according to ASTM D465-15. The rosin oil can have an acid value of less than 150, less than 130, less than 110, less than 100, less than 80, less than 60, less than 50, less than 40, less than 20, less than 10, less than 5, or less than about 1 mg KOH/g of rosin oil, as measured according to ASTM D465-15. The rosin oil can have an acid value of about 1 to about 150, about 1 to less than 150, about 1 to about 130, or about 50 to about 130 mg KOH/g of rosin oil, as measured according to ASTM D465-15. [0019] In at least one example, the wax composition can be made by mixing, blending, or otherwise combining the base wax and the rosin oil with one another. For example, a mixture that includes the base wax and the rosin oil can be heated to a temperature of about 80°C to about 200°C for at least 1 min, and then cooled to ambient temperature (e.g., less than 30°C, such as about 22°C to about 27°C) to produce the wax composition. The mixture can be agitated when heated. For example, the mixture that includes the base wax and the rosin oil can be agitated and heated to a temperature of about 90°C to about 150°C for about 2 min to about 120 min to produce the wax composition.

[0020] In at least one example, the base wax can be made by reacting together a dimer fatty acid a reagent. The reagent can be or include one or more amines, one or more alcohols, or any mixture thereof. The dimer acid can be mixed, blended, or otherwise combined with the reagent to produce a mixture that includes the dimer acid and the reagent. The mixture of the dimer acid and the reagent can be heated to a temperature of about 80°C, about 90°C, about 100°C, about 120°C, or about 150°C to about 175°C, about 200°C, about 225°C, about 250°C, about 275°C, or about 300°C to produce the base wax. The mixture of the dimer acid and reagent can be heated for about 0.5 hr, about 0.75 hr, about 1 hr, or about 1.25 hr to about 1.5 hr, about 2 hr, about 3 hr, about 4 hr, about 5 hr, about 6 hr, about 7 hr, about 8 hr, about 10 hr, about 12 hr, about 15 hr, about 18 hr, about 20 hr, about 24 hr, about 30 hr, about 40 hr, about 48 hr, or longer. For example, the third mixture can be heated for about 0.5 hr to about 48 hr, about 1 hr to about 24 hr, about 2 hr to about 12 hr, about 2 hr to about 10 hr, about 2 hr to about 8 hr, about 2 hr to about 6 hr, about 2 hr to about 4 hr, about 3 hr to about 12 hr, about 3 hr to about 10 hr, about 3 hr to about 8 hr, about 3 hr to about 6 hr, about 3 hr to about 4 hr, about 4 hr to about 12 hr, about 4 hr to about 10 hr, about 4 hr to about 8 hr, or about 4 hr to about 6 hr. In one specific example, the third mixture can be heated to greater than 80°C to about 300°C or about 1 10°C to about 280°C for about 1 hr to about 24 hr or about 2 hr to about 12 hr. The base wax can be mixed, blended, or otherwise combined with the rosin oil to produce the wax composition.

[0021] In at least one example, the dimer acid, the rosin oil, and the reagent (e.g., amines and/or alcohols) can be combined to produce a mixture. The mixture that includes the dimer acid, the rosin oil, and the reagent can be heated to a temperature of 80°C to about 300°C, and can be cooled, e.g., to ambient temperature, to produce the wax composition. In some examples, the mixture containing the dimer acid, the rosin oil, and the reagent can be heated to a temperature of about 100°C to about 250°C for at least 30 min to produce the wax composition. In another example, the mixture containing the dimer acid, the rosin oil, and the reagent can be heated to a temperature of about 140°C to about 200°C for about 45 min to about 180 min to produce the wax composition. After heating the mixture of the dimer acid and the reagent, the mixture can be cooled to a temperature of less than 40°C, less than 35°C, less than 30°C, or less than 25°C to provide the base wax. In another example, after heating the mixture of the dimer acid and the reagent, the mixture can be cooled to a temperature of about 10°C, about 15°C, or about 20°C to about 25°C, about 30°C, or about 35°C to provide the base wax.

[0022] The weight ratio of the dimer acid to the reagent, i.e., the amine and/or the alcohol, can be from about 0.5: 1, about 1 : 1, about 1.5: 1, about 2: 1, or about 3 : 1 to about 5: 1, about 7: 1, about 10: 1, about 15: 1, about 20: 1, about 25: 1, or about 30: 1. For example, the weight ratio of the dimer acid to the reagent can be about 1 : 1 to about 20: 1, about 1.5: 1 to about 10: 1, about 1 : 1 to about 7: 1, or about 1 : 1 to about 12: 1.

[0023] The dimer acids that can be used to make the base wax can be produced, derived, or otherwise made from one or more monomer acids, one or more dimer acids, one or more trimer acids, other oligomeric acids, or any mixture thereof. In at least one example, the dimer acids can be produced from one or more monomer fatty acids, one or more monomer rosin acids, or a mixture of one or more monomer fatty acids and one or more monomer rosin acids. Fatty acids can also derive from a fatty acid ester, a mixture of fatty acid esters, a fatty acid amide, a mixture of fatty acid amides, a mixture of one or more fatty acids and one or more fatty acid esters, a mixture of one or more fatty acids and one or more fatty acid amides, or a mixture of one or more fatty acids, one or more fatty acid esters, and one or more fatty acid amides. The monomer fatty acid and the monomer rosin acid can independently include one or more Ci ₆ -monomer acids, Cn-monomer acids, Ci ₈ -monomer acids, Ci ₉ -monomer acids, or C ₂ o-monomer acids. In some examples, the monomer fatty acid and the monomer rosin acid can independently include one or more compounds having the molecular formula of Ci6H ₂ 60 ₂ , Ci6H ₂₈ 0 ₂ , Ci6H ₃ o0 ₂ , Ci6H ₃₂ 0 ₂ , Ci ₈ H ₃ o0 ₂ , Ci ₈ H ₃₂ 0 ₂ , Ci ₈ H ₃ 40 ₂ , Ci ₈ H ₃₆ 0 ₂ , C ₂ oH ₃ 40 ₂ , C ₂ oH ₃₂ 0 ₂ , C ₂ oH ₃ o0 ₂ , or C ₂ oH ₂₈ 0 ₂ .

[0024] In other example, the dimer acid can include one or more C ₃ o-dimer acids, one or more C ₃₂ -dimer acids, one or more C ₃ 4-dimer acids, one or more C ₃₆ -dimer acids, one or more C ₃₈ - dimer acids, one or more C4o-dimer acids, one or more C42-dimer acids, or one or more C44- dimer acids. In some examples, the dimer acid can include one or more compounds having the molecular formula of C ₃ 6H ₆₂ 0 ₄ , C ₃₆ H ₆₄ 0 ₄ , C ₃₆ H ₆₆ 0 ₄ , C ₃₆ H ₆₈ 0 ₄ , C ₃₆ H ₇ o0 ₄ , C ₃₈ H ₆₂ 0 ₄ , C ₃₈ H ₆₄ 0 ₄ , C ₃₈ H ₆₆ 0 ₄ , C ₃₈ H ₆₈ 0 ₄ , or C ₄ oH ₆ o0 ₄ . In some examples, the dimer acid can be or include one or more homomeric acids that are dimer acids, where the monomer acid units in the dimer acid are the same. In some examples, the dimer acid can be or include one or more heteromeric acids that are dimer acids, where the monomer acid units in the dimer acid are different. In other examples, the dimer acid can be or include one or more heteromeric acids that are dimer acids formed from two different monomer rosin acids. In other examples, the dimer acid can be or include one or more heteromeric acids that are dimer acids formed from a monomer fatty acid and a monomer rosin acid. For example, the heteromeric dimer having the molecular formula of C ₃₈ H ₆₄ 0 ₄ , can be formed from a monomer fatty acid having the molecular formula of Ci ₈ H ₃₄ 0 ₂ and a monomer rosin acid having the molecular formula of C ₂ oH ₃ o0 ₂ . In other examples, the dimer acid can include one or more heteromeric compounds that can be formed from a monomer acids and a monomer rosin oil. For example, the heteromeric compound having the molecular formula of C^H _M C^, can be formed from a monomer fatty acid having the molecular formula of Ci ₈ H ₃₄ 0 ₂ and a monomer rosin oil having the molecular formula of C ₁₉ H ₀ .

[0025] Illustrative monomer fatty acids can include, but are not limited to, oleic acid, palmitic acid, linoleic acid, linolenic acid, eicosatrienoic acid, stearic acid, arachidic acid, behenic acid, isomers thereof, or any mixture thereof. Illustrative monomer rosin acids can be or include, but are not limited to, abietic acid, pimaric acid, dehydroabietic acid, palustric acid, isopimaric acid, neoabietic acid, sandaroco-pimaric acid, levopimaric acid, isomers thereof, or any mixture thereof.

[0026] In some examples, the dimer acids can be derived or otherwise produced from one or more fatty acid sources. Fatty acid sources from which the fatty acids can be derived can include, but are not limited to, tall oil fatty acids ("TOFA"), crude tall oils ("CTO"), distilled tall oils ("DTO"), depitched tall oil, tall oil pitches, plant and/or vegetable oils, animal fats or oils, portions thereof, fractions thereof, or any mixture thereof. As used herein, the term crude tall oil ("CTO") refers to the crude by-product, and only the crude by-product, recovered as soap skimmings from the black liquor of a Kraft pulping process. The term crude tall oil ("CTO"), as used herein, purposefully excludes any derivatives and intermediates produced from extraction or distillation.

[0027] In some examples, the fatty acid source can be heated to a temperature of about 200°C to about 400°C for at least 30 min to produce the dimer acid. In other examples, the fatty acid source can be heated to a temperature of about 200°C to about 400°C, about 250°C to about 350°C, about 275°C to about 325°C, or about 290°C to about 310°C for about 40 minutes, about 1 hr, about 1.5 hr, or about 2 hr to about 3 hr, about 3.5 hr, about 4 hr, or about 6 hr to produce the dimer acid. The fatty acid source can be heated in air and/or under an oxygen lean atmosphere such as nitrogen or argon atmosphere.

[0028] The components of the CTO can depend on a variety of factors, such as the particular species of the wood being processed (wood type), the geographical location of the wood source, the age of the wood, the particular season that the wood is harvested, and other factors. Thus, depending on the particular source, the CTO can contain about 20 wt% to about 75 wt% of fatty acids (e.g., about 30 wt% to about 60 wt% of fatty acids), about 20 wt% to about 65 wt% of rosin acids (e.g., about 30 wt% to about 60 wt% of rosin acids), and the balance being neutral and non- saponifiable components. In some examples, the CTO can include at least 3 wt%, at least 5 wt%, at least 8 wt%, or at least 10 wt% of neutral materials or non-saponifiable components.

[0029] The CTO and the DTO can contain saturated and unsaturated fatty acids in the C^-C^ range. The DTO can have a fatty acids and/or esters of fatty acids concentration of about 55 wt%, about 60 wt%, or about 65 wt% to about 85 wt%, about 90 wt%, or about 95 wt%. The DTO can have a rosin acids or rosins concentration of about 5 wt%, about 10 wt%, or about 15 wt% to about 30 wt%, about 35 wt%, or about 40 wt%. The DTO can have a neutrals concentration of about 0.1 wt%, about 1 wt%, or about 1.5 wt% to about 2 wt%, about 3.5 wt%, or about 5 wt%. The DTO can have an acid value of about 20, about 25, or about 30 to about 40, about 45, or about 50, as measured according to ASTM D465-15. The DTO can have a viscosity (centipoise at 85°C) of about 10 cP, about 20 cP, about 30 cP, or about 40 cP to about 100 cP, about 120 cP, about 135 cP, or about 150 cP. The DTO can have a density of about 840 g/L, about 860 g/L, or about 880 g/L to about 900 g/L, about 920 g/L, or about 935 g/L. The DTO can have a saponification number of about 180, about 185, or about 190 to about 200, about 205, or about 210. The DTO can have an iodine value of about 115, about 117, or about 120 to about 130, about 135, or about 140.

[0030] Commercially available tall oil products can include XTOL ^® 100, XTOL ^® 300, XTOL ^® 304, XTOL ^® 520, and XTOL ^® 3030, which are available from Georgia-Pacific Chemicals LLC, Atlanta, GA. XTOL ^® 100 can include about 1.6 wt% of palmitic acid, about 2.5 wt% of stearic acid, about 37.9 wt% of oleic acid, about 26.3 wt% of linoleic acid, about 0.3 wt% of linolenic acid, about 2.9 wt% of linoleic isomers, about 0.2 wt% of arachidic acid, about 3.6 wt% eicosatrienoic acid, about 1.4 wt% of pimaric acid, less than 0.16 wt% of sandarocopimaric, less than 0.16 wt% of isopimaric acid, less than 0.16 wt% of dehydroabietic acid, about 0.2 wt% of abietic acid, with the balance being neutrals and high molecular weight species. XTOL ^® 520 DTO includes about 0.2 wt% of palmitic acid, about 3.3 wt% of stearic acid, about 37.9 wt% of oleic acid, about 26.3 wt% of linoleic acid, about 0.3 wt% of linolenic acid, about 2.9 wt% of linoleic isomers, about 0.2 wt% of arachidic acid, about 3.6 wt% eicosatrienoic acid, about 1.4 wt% of pimaric acid, less than 0.16 wt% wt% of sandarocopimaric, less than 0.16 wt% of isopimaric acid, less than 0.16 wt% of dehydroabietic acid, about 0.2 wt% of abietic acid, with the balance being neutrals and high molecular weight species. Commercially available tall oil products include LYTOR ^® 100, LYTOR ^® 105, LYTOR ^® 105K, LYTOR ^® 110, and LYTOR ^® 307, which are commercially available from Georgia-Pacific Chemicals LLC, Atlanta, GA. LYTOR ^® 100 includes less than 0.16 wt% of palmitic acid, less than 0.16 wt% of stearic acid, about 0.2 wt% of oleic acid, about 0.2 wt% of arachidic acid, about 0.2 wt% eicosatrienoic acid, about 2.2 wt% of pimaric acid, about 0.6 wt% of sandarocopimaric, about 8.5 wt% of palustric acid, about 1.6 wt% of levopimaric acid, about 2.8 wt% of isopimaric acid, about 15.3 wt% of dehydroabietic acid, about 51.4 wt% of abietic acid, about 2.4 wt% of neoabietic acid, with the balance being neutrals and high molecular weight species.

[0031] Illustrative plant and/or vegetable oils can include, but are not limited to, safflower oil, grapeseed oil, sunflower oil, walnut oil, soybean oil, cottonseed oil, coconut oil, corn oil, olive oil, palm oil, palm olein, peanut oil, rapeseed oil, canola oil, sesame oil, hazelnut oil, almond oil, beech nut oil, cashew oil, macadamia oil, mongongo nut oil, pecan oil, pine nut oil, pistachio oil, grapefruit seed oil, lemon oil, orange oil, watermelon seed oil, bitter gourd oil, buffalo gourd oil, butternut squash seed oil, egusi seed oil, pumpkin seed oil, borage seed oil, blackcurrant seed oil, evening primrose oil, acai oil, black seed oil, flaxseed oil, carob pod oil, amaranth oil, apricot oil, apple seed oil, argan oil, avocado oil, babassu oil, ben oil, borneo tallow nut oil, cape chestnut, algaroba oil, cocoa butter, cocklebur oil, poppyseed oil, cohune oil, coriander seed oil, date seed oil, dika oil, false flax oil, hemp oil, kapok seed oil, kenaf seed oil, lallemantia oil, mafura oil, marula oil, meadowfoam seed oil, mustard oil, okra seed oil, papaya seed oil, perilla seed oil, persimmon seed oil, pequi oil, pili nut oil, pomegranate seed oil, prune kernel oil, quinoa oil, ramtil oil, rice bran oil, royle oil, shea nut oil, sacha inchi oil, sapote oil, seje oil, taramira oil, tea seed oil, thistle oil, tigernut oil, tobacco seed oil, tomato seed oil, wheat germ oil, castor oil, colza oil, flax oil, radish oil, salicornia oil, lung oil, honge oil, jatropha oil, jojoba oil, nahor oil, paradise oil, petroleum nut oil, dammar oil, linseed oil, stillingia oil, vernonia oil, amur cork tree fruit oil, artichoke oil, balanos oil, bladderpod oil, brucea javanica oil, burdock oil, candlenut oil, carrot seed oil, chaulmoogra oil, crambe oil, croton oil, cuphea oil, mango oil, neem oil, rose hip seed oil, rubber seed oil, sea buckthorn oil, sea rocket seed oil, snowball seed oil, tall oil, tamanu oil, tonka bean oil, ucuhuba seed oil, or any mixture thereof. Illustrative animal fats or oils that can be used as the fatty acids can include, but are not limited to, fatty acids from animal sources, such as cows, pigs, lambs, chickens, turkeys, ducks, geese, and other animals, as well as dairy products such as milk, butter, or cheese. Illustrative fatty acids from animal sources can include palmitic acid, stearic acid, myristic acid, oleic acid, palmitoleic acid, linoleic acid, or any mixture thereof.

[0032] It has been surprisingly and unexpectedly discovered that the rosin oil and dimer acid used to produce the base wax can be made or produced in situ from a single, cost effective feedstock. For example, a mixture of monomer fatty acids and monomer rosin acids can be converted to a mixture that includes the dimer acid and the rosin oil. The mixture that includes fatty acids and rosin acids can derive from a single feedstock or source that contains a mixture of rosin acids, fatty acids, sterols, high-molecular weight alcohols, and other alkyl chain materials. Such single feedstock or source can derive from tall oil, crude tall oil (CTO), distilled tall oil (DTO), or any mixture thereof including a mixture thereof with any one or more, two or more, or three or more intermediates of the DTO. In at least one example, the dimer fatty acid and the rosin oil can be produced in situ from a mixture of tall oil fatty acids, tall oil rosin acids. It was also surprising an unexpected that transparent to translucent wax compositions could be produced directly from crude tall oil. [0033] In one example, the dimer acid and the rosin oil can be made in situ can include mixing, blending, or otherwise combing a first catalyst with a mixture that includes a mixture of fatty acids and rosin acids, e.g., CTO, DTO, TOFA, tall oil rosin acids, or any mixture thereof to produce a first mixture. The first mixture can be heated to a first temperature to produce a first reaction mixture. In some examples, a second catalyst and the first reaction mixture can be mixed or otherwise combined and heated to a second temperature to produce a second reaction mixture. In other examples, the second catalyst can be omitted and the first reaction mixture, without the second catalyst, can be heated to the second temperature to produce the second reaction mixture.

[0034] In some examples, when the first catalyst and the mixture of fatty acids and rosin acids are mixed, an iron source, a nitrogen source, and an iodine source can be added in succession to the mixture of fatty acids and rosin acids. The first catalyst can be or can include nickel, palladium, platinum, iron, copper, cobalt, manganese, tin, sulfur, iodine, selenium source or a combination thereof. The first catalyst also can be or can include one or more iron sources, one or more nitrogen sources, one or more iodine sources, one or more sulfur sources or any mixture thereof. The iron source can be or can include metallic iron, ferric compounds, and ferrous compounds, including, but not limited to iron halides, iron oxides, iron hydroxides, iron sulfides, organic-iron compounds, or any mixture thereof. Illustrative iron sources can include one or more of metallic iron, ferrous chloride, ferric chloride, ferrous iodide, ferric iodide, ferrous bromide, ferric bromide, ferrous oxide, ferric oxide, ferrous hydroxide, ferric hydroxide, ferrous sulfide, ferric sulfide, ferrous selenide, ferric selenide, hydrates thereof, or any mixture thereof. Nitrogen sources can include one or more ammonium compounds, one or more amine compounds, one or more urea compounds, or any mixture thereof. Illustrative nitrogen sources can include ammonium carbonate, a mixture of carbonate and carbamate, urea carbonate, urea, dimethylurea, tetramethylurea, ammonium chloride, ammonium bromide, ammonium iodide, ammonium hydroxide, alkanolamines, ethylenediamine, diethylenetriamine, or any mixture thereof. Illustrative iodine sources can include elemental iodine (I ₂ ), iodide salts of alkaline metals {e.g., lithium iodide, sodium iodide, potassium iodide, cesium iodide), iodide salts of rare earth metals {e.g., magnesium iodide or calcium iodide), transition metal iodides {e.g., ferrous or ferric iodide), or any mixture thereof. In some examples, the iron source can be or can include one or more iron halides, the nitrogen source can be or can include ammonium carbonate or ethylenediamine, and the iodine source can be or can include elemental iodine. If the iron source is an iron chloride, then the iron source can be or can include ferric chloride, ferrous chloride, hydrates thereof, or any mixture thereof. In some examples, the iron source and the iodine source can both be or include ferrous iodide or ferric iodide. Illustrative sulfur sources can include an alkylphenol sulfide, a phenol sulfide, 2-2'-thiobis(4-methyl-6-t-butylphenol), l-thio-2- naphthol, l,l '-di-(2-naphthol)-disulfide, l, l '-di(2-naphthol)-sulfide, 2,5-diphenyl dithiin, 1,3,4- thiadiazole polysulfides, 4,4'-thiobis(resorcinol), 2,2'-thiobis(4,6-dimethylphenol), or any combination thereof.

[0035] The first mixture can include the first catalyst in an amount of about 0.01 wt%, about 0.02 wt%, about 0.03 wt%, about 0.05 wt%, about 0.07 wt%, about 0.1 wt%, about 0.15 wt%, or about 0.2 wt% to about 0.25 wt%, about 0.3 wt%, about 0.35 wt%, about 0.4 wt%, about 0.45 wt%, about 0.5 wt%, about 0.55 wt%, about 0.6 wt%, about 0.65 wt%, about 0.7 wt%, about 0.75 wt%, about 0.8 wt%, about 0.85 wt%, about 0.9 wt%, about 1 wt%, about 1.2 wt%, about 1.4 wt%, about 1.6 wt%, about 1.8 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, about 4.5 wt%, or about 5 wt%, based on the total or combined weight of the fatty acids and the rosin acids. For example, the first mixture can include the first catalyst in an amount of about 0.01 wt% to about 2 wt%, about 0.03 wt% to about 2 wt%, about 0.05 wt% to about 2 wt%, about 0.1 wt% to about 1.5 wt%, about 0.1 wt% to about 1 wt%, about 0.1 wt% to about 0.8 wt%, about 0.1 wt% to about 0.6 wt%, about 0.1 wt% to about 0.5 wt%, about 0.2 wt% to about 1.5 wt%, about 0.2 wt% to about 1 wt%, about 0.2 wt% to about 0.6 wt%, about 0.2 wt% to about 0.5 wt%, about 0.4 wt% to about 1.5 wt%, about 0.4 wt% to about 1 wt%, about 0.4 wt% to about 0.8 wt%, about 0.4 wt% to about 0.6 wt%, about 0.5 wt% to about 1.5 wt%, about 0.5 wt% to about 1 wt%, or about 0.5 wt% to about 0.8 wt%, about 0.01 wt% to about 1 wt%, about 0.03 wt% to about 1 wt%, about 0.05 wt% to about 1 wt%, about 0.01 wt% to about 0.5 wt%, about 0.03 wt% to about 0.5 wt%, about 0.05 wt% to about 0.5 wt%, about 0.01 wt% to about 0.1 wt%, about 0.03 wt% to about 0.1 wt%, about 0.05 wt% to about 0.1 wt%, based on the combined weight of the fatty acids and the rosin acids.

[0036] The first temperature can be about 50°C, about 80°C, about 100°C, about 120°C, about 150°C, or about 180°C to about 190°C, about 200°C, about 210°C, about 220°C, about 225°C, about 230°C, about 235°C, about 240°C, about 245°C, about 250°C, about 255°C, about 260°C, about 265°C, or about 270°C, to produce the first reaction mixture. For example, the first mixture can be heated to about 50°C to about 270°C, about 50°C to about 260°C, about 50°C to about 250°C, about 100°C to about 250°C, about 150°C to about 250°C, about 180°C to about 250°C, about 200°C to about 250°C, about 220°C to about 250°C, about 230°C to about 250°C, about 100°C to about 230°C, about 150°C to about 230°C, about 180°C to about 230°C, about 200°C to about 230°C, or about 220°C to about 230°C. In other examples, the first mixture that includes the first catalyst, the fatty acids, and the rosin acids can be heated to about 50°C to less than 270°C, about 50°C to less than 260°C, about 100°C to less than 260°C, about 150°C to less than 260°C, about 180°C to less than 260°C, about 200°C to less than 260°C, about 220°C to less than 260°C, about 50°C to less than 250°C, about 100°C to less than 250°C, about 150°C to less than 250°C, about 180°C to less than 250°C, about 200°C to less than 250°C, or about 220°C to less than 250°C. The first mixture can be heated to the first temperature for about 1 min, about 5 min, about 10 min, or about 15 min to about 20 min, about 30 min, about 1 hr, about 2 hr, about 3 hr, about 4 hr, about 6 hr, or longer to produce the first reaction mixture. For example, the first mixture can be heated for about 1 min to about 6 hr, about 1 min to about 4 hr, about 1 min to about 2 hr, about 1 min to about 1 hr, about 1 min to about 30 min, about 1 min to about 20 min, about 1 min to about 8 min, about 10 min to about 4 hr, about 10 min to about 5 hr, or about 10 min to about 1 hr. The first mixture can be heated to about 150°C or about 180°C to 250°C or less than 250°C for about 1 min to about 30 min or about 5 min to about 20 min to produce the first reaction mixture. In some examples, one or more acids, such as oxalic acid, can be added to the first reaction mixture to quench the first catalyst, ceasing the disproportionation reaction, and bleaching the first reaction mixture.

[0037] In some examples, the first mixture that includes fatty acids and rosin acids can have a first dehydroabietic acid concentration. The first reaction mixture can have a second dehydroabietic acid concentration. The second dehydroabietic acid concentration can be greater than the first dehydroabietic acid concentration. The first reaction mixture, therefore, can have an enriched dehydroabietic acid concentration relative to the first mixture that includes fatty acids and rosin acids. The first reaction mixture has an enriched dehydroabietic acid concentration, in part, due to the disproportionation reaction that produces the first reaction mixture. The first dehydroabietic acid concentration can be about 0.5 wt%, about 1 wt%, about 2 wt%, or about 3 wt% to about 4 wt% about 5 wt%, about 7 wt%, about 9 wt%, about 10 wt%, or about 12 wt%, based on the combined weight of the fatty acids and the rosin acids. For example, the first dehydroabietic acid concentration can be about 1 wt% to about 10 wt%, about 2 wt% to about 8 wt%, about 2 wt% to about 5 wt%, about 3 wt% to about 5 wt%, about 3 wt% to about 10 wt%, about 3 wt% to about 8 wt%, or about 5 wt% to about 8 wt%, based on the combined weight of the fatty acids and the rosin acids.

[0038] The first reaction mixture can have a second dehydroabietic acid concentration of about 1 wt%, about 2 wt%, about 3 wt%, or about 5 wt% to about 7 wt%, about 9 wt%, about 10 wt%, about 12 wt%, about 10 wt%, about 12 wt%, about 15 wt%, about 18 wt%, about 20 wt%, about 22 wt%, about 25 wt%, or about 30 wt%, based on the combined weight of the fatty acids and the rosin acids. For example, the second dehydroabietic acid concentration can be about 1 wt% to about 30 wt%, about 2 wt% to about 25 wt%, about 2 wt% to about 20 wt%, about 5 wt% to about 25 wt%, about 5 wt% to about 20 wt%, about 5 wt% to about 15 wt%, or about 5 wt% to about 12 wt%, based on the combined weight of the fatty acids and the rosin acids. The enriched dehydroabietic acid ratio, such as the second dehydroabietic acid concentration to the first dehydroabietic acid concentration, of the first reaction mixture can be greater than 1, about 1.5, about 2, about 2.5, about 3, about 3.5, about 4, about 4.5, about 5, about 6, about 7, about 8, about 9, about 10, about 12, about 15, or about 20.

[0039] In some examples, the second catalyst and the first reaction mixture can be mixed, blended, or otherwise combined to produce the second mixture. In other examples, the second catalyst can be omitted and the first reaction mixture can be further heated to produce the second reaction mixture. The second catalyst can be or can include one or more acids, such as, for example, one or more Bransted acids and/or one or more Lewis acids. Illustrative Bransted acids can be or can include methanesulfonic acid, p-toluenesulfonic acid (4- methylbenzenesulfonic acid), phosphoric acids, orthophosphoric acid, metaphosphoric acid, pyrophosphoric acid, sulfuric acid, isomers thereof, salts thereof, esters thereof, or any mixture thereof. Illustrative Lewis acids can be or can include one or more clays, such as, for example, montmorillonite. The second catalyst can also be or include one or more metal-containing compounds, such as zinc compounds, aluminum compounds, iron compounds, tin compounds, or any mixture thereof. In some examples, metal-containing compounds can be or can include one or more metal halides, such as, but not limited to, zinc chloride, aluminum chloride, iron chlorides, tin chlorides, or any mixture thereof. The second catalyst can also be or include a clay, such as for example, hectorite, montmorillonite, attapulgite, halloysite, kaolinite, sepiolite, bentonite, calcium bentonite, Fuller's Earth, acid-treated clay, acid-treated bentonite, acid-treated montmorillonite, alkaline clay, alkaline earth metal halide, lithium hydroxide, lithium carbonate, or acidic ion exchange resins such as Amberlyst 15, zinc halides, zinc chloride, zinc, bromide, zinc halides in presence of hydrogen halides, magnesium silicates, magnesium silicates in presence of nitrogenous compounds, stannic halides, stannic chloride, and/or stannic bromide.

[0040] The second mixture can include the second catalyst in an amount of about 0.05 wt%, about 0.07 wt%, about 0.1 wt%, about 0.15 wt%, or about 0.2 wt% to about 0.25 wt%, about 0.3 wt%, about 0.35 wt%, about 0.4 wt%, about 0.45 wt%, about 0.5 wt%, about 0.55 wt%, about 0.6 wt%, about 0.65 wt%, about 0.7 wt%, about 0.75 wt%, about 0.8 wt%, about 0.9 wt%, about 1 wt%, about 1.2 wt%, about 1.4 wt%, about 1.6 wt%, about 1.8 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, about 4.5 wt%, or about 5 wt%, based on the combined weight of the fatty acids and the rosin acids in the first mixture. For example, the second mixture can include the second catalyst in an amount of about 0.05 wt% to about 3 wt%, about 0.05 wt% to about 2.5 wt%, about 0.05 wt% to about 2 wt%, about 0.1 wt% to about 1.5 wt%, about 0.1 wt% to about 1 wt%, about 0.1 wt% to about 0.8 wt%, about 0.1 wt% to about 0.6 wt%, about 0.1 wt% to about 0.5 wt%, about 0.2 wt% to about 1.5 wt%, about 0.2 wt% to about 1 wt%, about 0.2 wt% to about 0.8 wt%, about 0.2 wt% to about 0.6 wt%, about 0.2 wt% to about 0.5 wt%, about 0.4 wt% to about 1.5 wt%, about 0.4 wt% to about 1 wt%, about 0.4 wt% to about 0.8 wt%, about 0.4 wt% to about 0.6 wt%, about 0.5 wt% to about 1.5 wt%, about 0.5 wt% to about 1 wt%, about 0.5 wt% to about 0.8 wt%, or about 0.5 wt% to about 0.7 wt%, based on the combined weight of the fatty acids and the rosin acids in the first mixture.

[0041] In at least one example, the second temperature can be greater than the first temperature. The second temperature can be about 250°C, about 252°C, about 255°C, or about 260°C to about 265°C, about 270°C, about 275°C, about 280°C, about 285°C, about 290°C, about 295°C, about 300°C, about 310°C, about 320°C, about 330°C, about 340°C, about 350°C, about 400°C, about 450°C, or about 500°C to produce the second reaction mixture. For example, the second mixture can be heated to a temperature greater than 250°C to about 500°C, greater than 250°C to about 400°C, greater than 250°C to about 350°C, greater than 250°C to about 330°C, greater than 250°C to about 320°C, greater than 250°C to about 310°C, greater than 250°C to about 300°C, or greater than 250°C to about 280°C. In other examples, the second mixture can be heated to about 280°C to about 350°C, about 280°C to about 330°C, about 280°C to about 320°C, or about 280°C to about 300°C to produce the second reaction mixture.

[0042] The second mixture can be heated for about 0.5 hr, about 0.75 hr, about 1 hr, or about 1.25 hr to about 1.5 hr, about 2 hr, about 3 hr, about 4 hr, about 5 hr, about 6 hr, about 7 hr, about 8 hr, about 10 hr, about 12 hr, about 15 hr, about 18 hr, about 20 hr, about 24 hr, about 30 hr, about 40 hr, about 48 hr, or longer to produce the second reaction mixture. For example, the second mixture can be heated for about 0.5 hr to about 48 hr, about 1 hr to about 24 hr, about 2 hr to about 12 hr, about 2 hr to about 10 hr, about 2 hr to about 8 hr, about 2 hr to about 6 hr, about 2 hr to about 4 hr, about 3 hr to about 12 hr, about 3 hr to about 10 hr, about 3 hr to about 8 hr, about 3 hr to about 6 hr, about 3 hr to about 4 hr, about 4 hr to about 12 hr, about 4 hr to about 10 hr, about 4 hr to about 8 hr, or about 4 hr to about 6 hr to produce the second reaction mixture. In one specific example, the second mixture can be heated to greater than 250°C to about 350°C or about 280°C to about 320°C for about 1 hr to about 24 hr or about 2 hr to about 12 hr to produce the second reaction mixture.

[0043] The second reaction mixture can include oligomeric acids produced from the fatty acids and/or rosin acids. The second reaction mixture also can include rosin oils produced from the rosin acids. The second reaction mixture can have a rosin oil yield of greater than 25%, greater than 30%), greater than 32%, greater than 35%, greater than 37%, greater than 40%, or greater than 42%. For example, the second reaction mixture can have a rosin oil yield of about 25% to about 95%; about 25% to about 85%; about 27% to about 77%; or about 32% to about 67%.

[0044] The rosin oil in the second reaction mixture can include rosin acids in an amount of less than 60 wt%, less than 50 wt%, less than 40 wt%, less than 30 wt%, less than 25 wt%, less than 23 wt%, less than 20 wt%, less than 17 wt%, less than 15 wt%, less than 10 wt%, less than 7 wt%, less than 5 wt%, less than 3 wt%, or less than 1 wt%. For example, the rosin oil can include rosin acids in an amount of about 0.01 wt% to less than 15 wt%, about 0.01 wt% to less than 10 wt%, about 0.01 wt% to less than 5 wt%, about 1 wt% to less than 15 wt%, or about 0.01 wt% to less than 25 wt%.

[0045] The rosin oil in the second reaction mixture can have an acid value of about 1, about 20, about 30, or about 50 to about 60, about 80, about 100, about 120, about 140, or about 150 mg KOH/g of rosin oil, as measured according to ASTM D465-15. The rosin oil can have an acid value of less than 150, less than 130, less than 1 10, less than 100, less than 80, less than 60, less than 50, less than 40, less than 20, less than 10, less than 5, or less than about 1 mg KOH/g of rosin oil, as measured according to ASTM D465-15. The rosin oil can have an acid value of about 1 to about 150, about 1 to less than 150, about 1 to about 130, or about 50 to about 130 mg KOH/g of rosin oil, as measured according to ASTM D465-15.

[0046] One or more chelating agents can be combined with the second reaction mixture and can be used to chelate and deactivate iron in the second reaction mixture. The chelating agent can be or can include one or more amines. Illustrative amines can include one or more monoamines, one or more polyamines (e.g., diamine or triamine), one or more alkanolamines, or any mixture thereof. The amine can be or can include one or more C2-C2o-monoamines, one or more C2-C20- diamines, one or more C ₃ -C ₂ o-triamines, salts thereof, or any mixture thereof. In some examples, the amine can be or can include one or more polyamines, such as one or more C ₂ -C ₅ -diamines. Illustrative amines or other basic or alkaline compounds useful as the second catalyst can include ethylamine, ethylenediamine, diethylenetriamine, propylamine, propylenediamine, laurylamine, octadecylamine, isomers thereof, salts thereof, or any mixture thereof. In some examples, the second catalyst and the chelator can be included into the mixture separately or together and can be or can include methanesulfonic acid, ethylenediamine, or a mixture thereof.

[0047] The second reaction mixture can include the chelating agent in an amount of about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, or about 0.5 wt% to about 0.6 wt%, about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1 wt%, about 1.2 wt%, about 1.4 wt%, about 1.6 wt%, about 1.8 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, about 4.5 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, or about 10 wt%, based on the combined weight of the fatty acids and the rosin acids in the first reaction mixture. For example, the second reaction mixture can include the chelating agent in an amount of about 0.1 wt% to about 10 wt%, about 0.1 wt% to about 8 wt%, about 0.1 wt% to about 5 wt%, about 0.1 wt% to about 3 wt%, about 0.1 wt% to about 1 wt%, about 1 wt% to about 10 wt%, about 1 wt% to about 5 wt%, or about 1 wt% to about 3 wt%, based on the combined weight of the fatty acids and the rosin acids in the first reaction mixture.

[0048] The rosin oil yield can be calculated by taking the weight percent of rosin oil produced in the second reaction mixture over the weight percent of rosin acid in the starting mixture that includes fatty acids and rosin acids (e.g., CTO or DTO). The second reaction mixture can have a rosin oil yield of greater than 25%, about 26%>, about 28%, about 30%>, or about 35% to about 36%, about 38%, about 40%, about 42%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, about 97%, about 98%), or about 99%. The second reaction mixture can have a rosin oil yield of greater than 25% to about 95%, about 30% to about 95%, about 30% to about 85%, about 35% to about 80%, about 40%) to about 95%, or about 40% to about 85%. In some examples, the second reaction mixture can have a rosin oil yield of about 30% to about 95% or about 35% to about 80%.

[0049] The second reaction mixture can be cooled to ambient temperature (about 23°C). The second reaction mixture can include oligomeric acids, e.g., a mixture of dimer acids and trimer acids, and rosin oil. The oligomeric acids can include one or more dimer acids, one or more trimer acids, one or more higher acids (e.g., acids containing 4, 5, or more monomer acid units), or any mixture thereof. The oligomeric acid can be or can include one or more homomeric acids and/or one or more heteromeric acids. The oligomeric acid can be produced from one or more monomer fatty acids that can include oleic acid, palmitic acid, linoleic acid, stearic acid, arachidic acid, behenic acid, isomers thereof, or any mixture thereof. The oligomeric acid can include one or more dimer acids and/or trimer acids. The oligomeric acid can have an acid value of about 100, about 150, or about 160 to about 170, about 200, about 250, or about 300 mg KOH/g of oligomeric acid. The oligomeric acid can have an acid value of about 150 to about 400, about 150 to about 300, about 160 to about 250, or about 170 to about 200 mg KOH/g of oligomeric acid.

[0050] The one or more reagents, i.e., one or more amines and/or one or more alcohols, can be mixed, blended, or otherwise combined with the second reaction mixture to produce a third mixture. The third mixture can be heated to a temperature of about 80°C, about 90°C, about 100°C, about 120°C, or about 150°C to about 175°C, about 200°C, about 225°C, about 250°C, about 275°C, or about 300°C to produce a third reaction mixture. The third mixture can be heated for about 0.5 hr, about 0.75 hr, about 1 hr, or about 1.25 hr to about 1.5 hr, about 2 hr, about 3 hr, about 4 hr, about 5 hr, about 6 hr, about 7 hr, about 8 hr, about 10 hr, about 12 hr, about 15 hr, about 18 hr, about 20 hr, about 24 hr, about 30 hr, about 40 hr, about 48 hr, or longer to produce the third reaction mixture. For example, the third mixture can be heated for about 0.5 hr to about 48 hr, about 1 hr to about 24 hr, about 2 hr to about 12 hr, about 2 hr to about 10 hr, about 2 hr to about 8 hr, about 2 hr to about 6 hr, about 2 hr to about 4 hr, about 3 hr to about 12 hr, about 3 hr to about 10 hr, about 3 hr to about 8 hr, about 3 hr to about 6 hr, about 3 hr to about 4 hr, about 4 hr to about 12 hr, about 4 hr to about 10 hr, about 4 hr to about 8 hr, or about 4 hr to about 6 hr. In one specific example, the third mixture can be heated to greater than 80°C to about 300°C or about 110°C to about 280°C for about 1 hr to about 24 hr or about 2 hr to about 12 hr to produce the third reaction mixture.

[0051] The third reaction mixture can be cooled to provide the base wax composition. For example, the third reaction mixture can be cooled to a temperature of less than 40°C, less than 35°C, less than 30°C, or less than 25°C to provide the wax composition. In another example, the third reaction mixture can be cooled to a temperature of about 10°C, about 15°C, or about 20°C to about 25°C, about 30°C, or about 35°C to provide the wax composition.

[0052] In another embodiment, the one or more reagents, i.e., one or more amines and/or one or more alcohols, can be mixed, blended, or otherwise combined with the second reaction mixture to produce a third mixture prior to cooling the second reaction mixture. Said another way, the second reaction mixture does not need to be cooled to a temperature below, e.g., 250°C or 100°C, or lower, before the reagent can be added thereto.

[0053] The amount of the reagent, i.e., the amine and/or the alcohol, combined with the second reaction mixture can be the same or similar to the amount of the reagent added to the dimer acid discussed and described above. For example, the weight ratio of the dimer acid to the reagent in the second mixture can be from about 0.5: 1, about 1 : 1, about 1.5: 1, about 2: 1, or about 3 : 1 to about 5: 1, about 7: 1, about 10: 1, about 15: 1, about 20: 1, about 25 : 1 , or about 30: 1. For example, the weight ratio of the dimer acid to the reagent can be about 1 : 1 to about 20: 1, about 1.5: 1 to about 10: 1, about 1 : 1 to about 7: 1, or about 1 : 1 to about 12: 1.

[0054] The amine that can be used as the reagent can be or include one or more C ₂ -C ₂₀ - monoamines, one or more C ₂ -C ₂ o-diamines, one or more C3-C ₂ o-triamines, salts thereof, or any mixture thereof. In some specific examples, the amine can include a C ₈ -C ₂ o-monoamine. Illustrative amines can include, but are not limited to, ethylamine, ethylenediamine, propylamine, propylenediamine, laurylamine, octadecylamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyethylenepolyamine, ethanolamine, diethanolamine, triethanolamine, piperazine, aminoethylpiperazine, aniline, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, o-xylenediamine, m-xylenediamine, p- xylenediamine, isomers thereof, salts thereof, or any mixture thereof. In one example, the amine can be or include laurylamine. In another example, the amine can be or include ethylenediamine. In one example, the amine can be or include octadecylamine, and the wax composition can have a melting point of about 48°C to about 60°C or about 50°C to about 54°C.

[0055] The alcohol that can be used as the reagent can be or include one or more C2-C24 or C ₈ - C ₂ o alcohols (e.g., mono-alcohols), one or more C ₂ -C ₂ o-polyols including diols, triols, or higher polyols (e.g., alcohols containing 4, 5, or more hydroxyl groups), salts thereof, esters thereof, or any mixture thereof. Illustrative alcohols can be or include, but are not limited to, stearyl alcohol (also known as 1-octadecanol); palmityl alcohol (also known as cetyl alcohol or 1-hexadecanol); myristyl alcohol (also known as 1 -tetradecanol); ethylene glycol, glycerine (also known as glycerol); 1,2-propylene glycol; 1,3-propylene glycol; 1,4-butene diol; phenol; catechol; resorcinol; hydroquinone; pentaerythritol; trimethylol ethane; trimethylolpropane; sugars, e.g., pentoses, hexoses, glucose, fructose, sorbitol, sucrose, and raffinose; isomers thereof; salts thereof; esters thereof; hydrates thereof; or any mixture thereof. Esters of polyols can be or include monoesters, diesters, or triesters.

[0056] The base wax can be or include one or more amides or polyamides (e.g., diamides, triamides, or amides containing 4, 5, or more amide groups) and/or one or more reaction products made, derived, or otherwise produced from one or more monomeric or oligomeric acids and one or more monomeric or oligomeric amines. In other examples, the base wax can be or include one or more alcohols or polyols (e.g., diols, triols, or alcohols containing 4, 5, or more hydroxyl groups) and/or one or more reaction products made, derived, or otherwise produced from one or more monomeric or oligomeric acids and one or more monomeric or oligomeric alcohols. In some specific examples, the base wax can include dilauryl diethylenetriamine and the wax composition can have a melting point of about 85°C to about 100°C or about 89°C to about 98°C.

[0057] The wax compositions discussed and described herein can be used in numerous applications. For example, the wax compositions can be used to make candles or fuels in the candle-making industry, can be used as a cosmetic or personal care material in the cosmetics and personal care industries, can be used as corrosion inhibitors in oilfield and metal-working applications, can be used in ink compositions for the printing ink applications, can be used as plasticizers and/or emulsifiers (e.g., tire manufacturing industry), can be used as a lubricant for hydraulic fluids, and/or can be used to provide desired viscosities and/or melting points for such materials.

Examples

[0058] In order to provide a better understanding of the foregoing discussion, the following non- limiting examples are offered. Although the examples can be directed to specific embodiments, they are not to be viewed as limiting the invention in any specific respect.

[0059] Examples 1-6: Wax compositions of dilauryl diethylenetriamine and rosin oil - About 500 g of rosin acid (LYTOR®100 tall oil rosin acid, available from Georgia-Pacific Chemicals LLC) was stirred in a flask and heated to a temperature of about 320°C for about 24 hr under a nitrogen atmosphere to produce a rosin oil. Rosin oil was mixed with dilauryl diethylenetriamine at different weight percent (wt%) values - as listed in Table 1 - to produce wax compositions. Rosin oil was varied from 0 wt% to about 90 wt%. The viscosities of the wax compositions were measured by a cone and plate rheometer as a function of temperature at a shear rate of about 1 Hz. The temperature was increased from about 25°C to about 125°C and held at 125°C for about 2 minutes and then decreased to 25°C.

[0060] The mixtures of dilauryl diethylenetriamine and rosin oil and were independently heated to a temperature of about 120°C, stirred, and allowed to cool to a temperature of about 22°C to about 27°C. Objectives included understanding what quantities of rosin oil could be incorporated into the base wax, such as dilauryl diethylenetriamine, while maintaining a wax -like property and understanding the effects of varying the concentration of rosin oil. The texture of the resulting compositions ranged from hard, tough materials to soft, greasy, silk like waxes dependent on the amount of rosin oil contained in the mixture. The viscosity at room temperature also varied greatly and appeared to depend on the amount of rosin oil present. Without rosin oil, the viscosity at about 33°C was about 29,500 Pa s. At about 10 wt% rosin oil, the viscosity of the composition decreased to about 26,500 Pa-s. At about 50 wt% rosin oil, the viscosity further decreased to about 13,500 Pa-s, and about 1,900 Pa-s at about 70 wt% rosin oil. [0061] While the texture and viscosity changed based upon the quantity of rosin oil, the melting point of the waxes remained fairly constant though a slight decrease in melting point was observed as the quantity of rosin oil increased. For example, the melting point of dilauryl diethylenetriamine was about 103°C, whereas the melting point of the mixture containing about 90 wt% rosin oil was about 89°C.

[0062] Example 7: Dimer fatty acid - About 500 g of TOFA (XTOL ^® 100 tall oil fatty acids, available from Georgia-Pacific Chemicals LLC) was first heated to about 300°C for about 2.5 hr under nitrogen atmosphere to produce a fatty acid dimer mixture with an acid value of 174 mg KOH per g of the fatty acid dimer mixture that also contained fatty acid monomers and fatty acid trimers.

[0063] Examples 8-10: Wax compositions - About 500 g of TOFA (commercially available as XTOL ^® 100 tall oil fatty acids, from Georgia-Pacific Chemicals LLC) was first heated to about 300°C for about 2.5 hr under a nitrogen atmosphere to produce a fatty acid dimer mixture with an acid value of 174 mg KOH per g of the fatty acid dimer mixture that also contained fatty acid monomers and fatty acid trimers. About 500 g of rosin acid (commercially available as LYTOR ^® 100 tall oil rosin acid, from Georgia-Pacific Chemicals LLC) was stirred in a flask and heated to a temperature of about 320°C for about 24 hr under a nitrogen atmosphere to produce a rosin oil. In Example 8, about 5 g of the dimer fatty acid mixture, about 5 g of rosin oil, and about 2.84 g of laurylamine were combined and stirred in a flask. The mixture was heated to a temperature of about 165°C and stirred for about 2 hr to make a wax composition that included the laurylamine and the rosin oil. In Example 9, about 5 g of the dimer fatty acid composition, about 5 g of rosin oil, and about 4.18 g of octadecylamine were combined and stirred in a flask. The mixture was heated to a temperature of about 165°C and stirred for about 2 hr to make a wax composition that included the octadecylamine and the rosin oil. In Example 10, about 5 g of the dimer fatty acid composition, about 5 g of rosin oil, and about 0.466 g of ethylenediamine were combined and stirred in a flask. The mixture was heated to a temperature of about 165°C and stirred for about 2 hr to make a wax composition that included the ethylenediamine and the rosin oil. In Examples 8-10, wax compositions were produced from a polyamide of a monomer/dimer fatty acid formed in the presence of rosin oil. In Example 8, the wax composition was a gel -like paste nearly in a liquid state. In Example 9, the wax composition was opaque and exhibited internal cracking and a rough surface. In Example 10, the wax composition was translucent to nearly transparent and had no internal cracking and a nearly defect free surface.

[0064] Example 11 : Wax compositions of polyamides from heat-treated CTO and acid catalyst - About 100 g of CTO (Crude Tall Oil, available from Georgia-Pacific Chemicals LLC) and about 0.714 g of an acid catalyst (about 0.5 wt% of 70% methanesulfonic acid) were combined and stirred in a flask to produce a mixture. The mixture of components was heated to a temperature of about 300°C for about 5 hr under a nitrogen atmosphere to produce a mixture of dimer fatty acid, oleic acid, dimerized TOFA and rosin acids, and rosin oils. Thereafter, about 7 g of the reaction mixture was combined with about 0.270 g of ethylenediamine under an air atmosphere and heated to a temperature of about 165°C for about 3 hr. The mixture was cooled to a temperature of about 22°C to about 27°C to produce a wax composition that was solid and wax -like.

[0065] Example 12: Wax compositions of polyamides from heat-treated CTO and acid catalyst - About 100 g of CTO (Crude Tall Oil, available from Georgia-Pacific Chemicals LLC) and about 0.588 g of an acid catalyst (about 0.5 wt% of 85% phosphoric acid) were combined and stirred in a flask to produce a mixture. The mixture of components was heated to a temperature of about 300°C for about 7 hr under a nitrogen atmosphere to produce a mixture of dimer fatty acid, oleic acid, dimerized TOFA and rosin acids, and rosin oils. Thereafter, about 7 g of the reaction mixture was combined with about 0.42 g of ethylenediamine under an air atmosphere and heated to a temperature of about 165°C for about 3 hr. The mixture was cooled to a temperature of about 22°C to about 27°C to produce a wax composition that was solid and waxlike.

[0066] Table 4 lists some of the physical properties of the produced wax compositions in Examples 11 and 12. The wax composition of Ex. 11 was harder than the wax composition of Ex. 12.

Table 5: Disproportionation of CTO

Fatty Acids: (wt%)

Palmitic Stearic Oleic Linoleics* Linolenic Arachidic Eicosatrienoic Total

CTO 3.2 1.1 15.7 15.9 0.2 0.2 1.6 37.9

230°C,

15 min 2.9 1.0 19.7 11.2 <0.2 0.2 0.9 35.9

230°C,

30 min 3.0 1.0 21.2 8.0 0.2 0.5 33.9

260°C,

60 min 3.2 1.1 27.0 2.5 0.2 <0.2 34.0

Rosin Acids: (wt%)

Sando- Levo- Dehydro-

Pimaric pimaric Palustric pimaric Isopimaric abietic Abietic Total

CTO 3.2 0.5 6.5 1.6 1.4 3.8 12.0 28.2

230°C,

15 min 0.3 0.5 0.2 <0.2 23.0 1.8 25.6

230°C,

30 min 0.2 0.4 <0.2 24.2 0.2 25.0

260°C,

60 min 0.2 0.4 <0.2 <0.2 24.4 25.0

* includes linoleic acid and isomers thereof.

[0067] Example 13 : Wax of polyamides from disproportionated and heat-treated CTO - To make the dimer acid and rosin oil composition, about 7.2 mg of FeCl ₃ , about 90 mg of I ₂ , about 36 mg of (NH ₄ ) ₂ C0 ₃ , and about 30 g of CTO (Crude Tall Oil, available from Georgia-Pacific Chemicals LLC) were combined and stirred in a flask and heated to a temperature of about 230°C for about 15 min to disproportionate the rosin components. This led to a mixture in which the rosin acids were converted almost exclusively to dehydroabietic acid. Hydrogen was transferred to linoleic acids in the dehydrogenation reaction, and the percentage of oleic acid increased as a result (Table 5). About 16 mg of ethylenediamine, about 214 mg of MeS0 ₃ H solution (about 70 wt% of MeS0 ₃ H and about 30 wt% of water), and the mixture were combined and heated to a temperature of about 300°C for about 4 hr to produce the mixture of dimer fatty acid, oleic acid, dimerized TOFA and rosin acids, and rosin oils. The acid value decreased from about 165 mg KOH/g of the mixture of dimer fatty acid, oleic acid, dimerized TOFA and rosin acids, and rosin oils to about 96.6 mg KOH/g of the mixture of dimer fatty acid, oleic acid, dimerized TOFA and rosin acids, and rosin oils (Table 6). Ethylenediamine (about 0.258 g) was added to about 5 g of the treated CTO and heated to a temperature of about 165°C for about 3 hr. Physical properties of the produced wax composition are listed in Table 6. In Example 13, the wax composition derived from CTO was made by first disproportionating the rosin components followed by a heated acid-treatment to dimerize the remaining fatty acids. By first obtaining dehydroabietic acid, the tendency to produce dimers of fatty acid with rosin acid was markedly reduced, as the reactivity of the olefinic bonds of rosin was reduced by aromatization.

[0068] Example 14: Wax of polyamides from monomer/dimer FA's and mineral oil - About 500 g of TOFA (XTOL ^® 100 tall oil fatty acids, available from Georgia-Pacific Chemicals LLC) was first heated to about 300°C for about 2.5 hr under a nitrogen atmosphere to produce fatty acid dimer mixture that contained fatty acid monomers and trimers. About 5 g of mineral oil, about 5 g of the fatty acid dimer mixture, and about 0.47 g of ethylenediamine were combined and stirred in a flask and heated to a temperature of about 165°C for about 2 hr to make the polyamide in mineral oil. Physical properties of the produced wax composition are listed in Table 7.

[0069] Embodiments of the present disclosure further relate to any one or more of the following paragraphs:

[0070] 1. A wax composition, comprising: a base wax; and a rosin oil having an acid value of less than 150 mg KOH/g of the rosin oil, wherein the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil, and has a viscosity of about 1,000 Pa-s to about 28,000 Pa-s at a temperature of about 25°C.

[0071] 2. A method for making a wax composition, comprising: heating and agitating a mixture comprising a base wax and a rosin oil to a temperature of about 80°C to about 200°C for at least 1 min; and cooling the mixture to a temperature of less than 30°C to produce a wax composition, wherein the rosin oil has an acid value of less than 150 mg KOH/g of the rosin oil, and wherein the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil, and has a viscosity of about 1,000 Pa s to about 28,000 Pa-s at about 25°C.

[0072] 3. A method for making a wax composition, comprising: combining a dimer acid, a rosin oil, and a reagent to produce a mixture, wherein the reagent comprises an amine, an alcohol, or a mixture thereof; heating the mixture comprising the dimer acid, the rosin oil, and the reagent to a temperature of about 80°C to about 300°C; and cooling the mixture to a temperature of less than 30°C to produce a wax composition, wherein the rosin oil has an acid value of less than 150 mg KOH/g of the rosin oil, and wherein the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil, and has a viscosity of about 1,000 Pa-s to about 28,000 Pa-s at about 25°C.

[0073] 4. The method according to paragraph 3, wherein a fatty acid source is heated to a temperature of about 200°C to about 400°C to produce the dimer acid.

[0074] 5. The method according to paragraph 3 or 4, further comprising: combining a catalyst and the fatty acid source to produce a mixture; and heating the mixture comprising the catalyst and the fatty acid source to produce the dimer acid.

[0075] 6. A method for making a wax composition, comprising: heating a mixture comprising a fatty acid source and a rosin acid source to a temperature of about 200°C to about 400°C to produce a product mixture comprising a dimer acid and a rosin oil; combining the product mixture and a reagent to produce a mixture comprising the dimer acid, the rosin oil, and the reagent, wherein the reagent comprises an amine, an alcohol, or a mixture thereof; heating the mixture comprising the dimer acid, the rosin oil, and the reagent to a temperature of about 80°C to about 300°C; and cooling the mixture to an ambient temperature of less than 30°C to produce a wax composition, wherein the rosin oil has an acid value of less than 150 mg KOH/g of the rosin oil, and wherein the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil, and has a viscosity of about 1,000 Pa-s to about 28,000 Pa-s at about 25°C. [0076] 7. The method according to paragraph 6, further comprising combining a catalyst, the fatty acid source, the rosin acid source to produce a mixture comprising the catalyst, the fatty acid source, and the rosin acid source; and heating the mixture comprising the catalyst, the fatty acid source, and the rosin acid source to produce the product mixture comprising the dimer acid and the rosin oil.

[0077] 8. A method for making a wax composition, comprising: heating a mixture comprising a fatty acid source and a rosin acid source to a temperature of about 200°C to about 400°C to produce a mixture comprising the fatty acid source and a rosin oil; combining a catalyst and the mixture comprising the fatty acid source and the rosin oil; heating the mixture comprising the catalyst, the fatty acid source, and the rosin oil to produce a product mixture comprising a dimer acid and a rosin oil; combining the product mixture and a reagent to produce a mixture comprising the dimer acid, the rosin oil, and the reagent, wherein the reagent comprises an amine, an alcohol, or a mixture thereof; heating the mixture comprising the dimer acid, the rosin oil, and the reagent to a temperature of about 80°C to about 300°C; and cooling the mixture to an ambient temperature of about 22°C to about 27°C to produce a wax composition, wherein the rosin oil has an acid value of less than 150 mg KOH/g, and wherein the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil, and has a viscosity of about 1,000 Pa-s to about 28,000 Pa-s at about 25°C.

[0078] 9. A method for making a wax composition, comprising: combining a first catalyst and a mixture comprising fatty acids and rosin acids to produce a first mixture, wherein the mixture comprising fatty acids and rosin acids has a first dehydroabietic acid concentration; heating the first mixture to a first temperature to produce a first reaction mixture, wherein the first reaction mixture has a second dehydroabietic acid concentration greater than the first dehydroabietic acid concentration; heating the first reaction mixture to a second temperature to produce a second reaction mixture; and cooling the second reaction mixture to a third temperature of about 20°C to about 50°C to produce a wax composition, wherein: the second temperature is greater than the first temperature, the second temperature is greater than 250°C, the second reaction mixture comprises oligomeric acids and rosin oils, the rosin oils are produced from the rosin acids, the rosin oil has an acid value of less than 150 mg KOH/g of the rosin oil, the second reaction mixture has a rosin oil yield of greater than 25%, and the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil, and has a viscosity of about 1,000 Pa-s to about 28,000 Pa-s at about 25°C.

[0079] 10. A method for making a wax composition, comprising: combining a first catalyst and a mixture comprising fatty acids and rosin acids to produce a first mixture; heating the first mixture at a first temperature to produce a first reaction mixture; combining a second catalyst and the first reaction mixture to produce a second mixture; heating the second mixture at a second temperature to produce a second reaction mixture; and cooling the second reaction mixture to a third temperature of about 20°C to about 50°C to produce a wax composition, wherein: the second temperature is greater than the first temperature, the second temperature is greater than 250°C, the second reaction mixture comprises oligomeric acids and rosin oils, the rosin oils are produced from the rosin acids, the rosin oil has an acid value of less than 150 mg KOH/g, the second reaction mixture has a rosin oil yield of greater than 25%, and the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil, and has a viscosity of about 1,000 Pa-s to about 28,000 Pa-s at about 25°C.

[0080] 11. The method according to paragraph 9 or 10, wherein the second reaction mixture has a rosin oil yield of about 30% to about 95%.

[0081] 12. The method according to paragraph 9 or 10, wherein the first catalyst comprises an iron source and an iodine source, or a mixture thereof.

[0082] 13. The method according to paragraph 9 or 10, wherein the fatty acids and the rosin acids are mixed with one another prior to mixing the first catalyst therewith, wherein an iron source and an iodine source are added in succession to the mixture comprising fatty acids and rosin acids.

[0083] 14. The method according to paragraph 13, wherein the iron source comprises an iron halide and the iodine source comprises elemental iodine (I ₂ ).

[0084] 15. The method according to paragraph 9, wherein the first catalyst comprises an iron source, a nitrogen source, an iodine source, or any mixture thereof. [0085] 16. The method according to paragraph 9 or 10, wherein the fatty acids and the rosin acids are mixed with one another prior to mixing the first catalyst therewith, wherein an iron source, a nitrogen source, and an iodine source are added in succession to the mixture comprising fatty acids and rosin acids.

[0086] 17. The method according to paragraph 16, wherein the iron source comprises an iron halide, the nitrogen source comprises an ammonium compound, an amine compound, an urea compound, or any mixture thereof, and the iodine source comprises elemental iodine (I ₂ ).

[0087] 18. The method according to paragraph 9 or 10, wherein the first catalyst is combined with the mixture comprising fatty acids and rosin acids in an amount of about 0.01 wt% to about 2 wt%, based on the combined weight of the fatty acids and the rosin acids.

[0088] 19. The method according to paragraph 9 or 10, wherein the mixture comprising the first catalyst, the fatty acids, and the rosin acids is heated to about 180°C to 250°C for about 1 min to about 30 min to produce the first reaction mixture.

[0089] 20. The method according to paragraph 9, wherein a second catalyst is combined with the first reaction mixture, and wherein the first reaction mixture comprising the second catalyst is heated to the second temperature to produce the second reaction mixture.

[0090] 21. The method according to paragraph 10 or 20, wherein the second catalyst comprises a Bransted acid or a Lewis acid, and wherein the second catalyst is added to the first reaction mixture.

[0091] 22. The method according to paragraph 10 or 20, wherein the second catalyst comprises methanesulfonic acid, p-toluenesulfonic acid, phosphoric acids, orthophosphoric acid, metaphosphoric acid, pyrophosphoric acid, sulfuric acid, isomers thereof, salts thereof, esters thereof, or any mixture thereof.

[0092] 23. The method according to paragraph 10 or 20, wherein the second catalyst is combined with the first reaction mixture in an amount of about 0.05 wt% to about 3 wt%, based on the combined weight of the fatty acids and the rosin acids.

[0093] 24. The method according to paragraph 10 or 20, wherein the mixture comprising the second catalyst and the first reaction mixture is heated to about 280°C to about 320°C for about 2 hr to about 12 hr to produce the second reaction mixture. [0094] 25. The method according to paragraph 10, wherein the mixture comprising fatty acids and rosin acids has a first dehydroabietic acid concentration, wherein the first reaction mixture has a second dehydroabietic acid concentration, and wherein the second dehydroabietic acid concentration is greater than the first dehydroabietic acid concentration.

[0095] 26. A wax composition, comprising: a base wax; and a rosin oil comprising a decarboxylated rosin acid and less than 25 wt% of rosin acids, wherein the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on a combined weight of the base wax and the rosin oil, and wherein the wax composition has a viscosity of about 1,000 Pa-s to about 28,000 Pa-s at a temperature of about 25°C.

[0096] 27. The wax composition according to paragraph 26, wherein the base wax comprises a reaction product made from reacting together dimer fatty acids and a reagent, wherein the reagent comprises an amine, an alcohol, or any mixture thereof.

[0097] 28. The wax composition according to paragraph 27, wherein the dimer fatty acids are derived from monomer fatty acids in crude tall oil, wherein the amine comprises ethylamine, ethylenediamine, propylamine, propylenediamine, laurylamine, octadecylamine, isomers thereof, salts thereof, or any mixture thereof, and wherein the alcohol comprises stearyl alcohol, palmityl alcohol, myristyl alcohol, ethylene glycol, glycerine, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butene diol, isomers thereof, salts thereof, esters thereof, hydrates thereof, or any mixture thereof.

[0098] 29. The wax composition according to any one of paragraphs 26 to 28, wherein the wax composition has a weight ratio of the base wax to the rosin oil of about 1 :9 to about 9: 1.

[0099] 30. A wax composition, comprising: a base wax; and a rosin oil comprising a decarboxylated rosin acid and less than 25 wt% of rosin acids, wherein the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on a combined weight of the base wax and the rosin oil.

[00100] 31. The wax composition according to paragraph 30, wherein the base wax comprises one or more polyamides. [00101] 32. The wax composition according to paragraph 30 or 31, wherein the base wax comprises dilauryl diethylenetriamine, and wherein the wax composition has a melting point of about 85°C to about 100°C.

[00102] 33. The wax composition according to any one of paragraphs 30 to 32, wherein: the base wax comprises a reaction product of a dimer fatty acid and an amine, the amine comprises the amine comprises ethylamine, ethylenediamine, propylamine, propylenediamine, laurylamine, octadecylamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyethylenepolyamine, ethanolamine, diethanolamine, triethanolamine, piperazine, aminoethylpiperazine, aniline, o-phenylenediamine, m-phenylenediamine, p- phenylenediamine, o-xylenediamine, m-xylenediamine, p-xylenediamine, or any mixture thereof, and the rosin oil comprises decarboxylated tall oil rosin acids.

[00103] 34. The wax composition according to paragraph 33, wherein a reaction mixture comprising the dimer fatty acid and the amine is reacted to produce the reaction product, and wherein a weight ratio of the dimer fatty acid to the amine is about 1 : 1 to about 20: 1.

[00104] 35. The wax composition according to any one of paragraphs 30 to 34, wherein: the base wax comprises a reaction product of a dimer fatty acid and an alcohol, the alcohol comprises stearyl alcohol, palmityl alcohol, myristyl alcohol, ethylene glycol, glycerine, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butene diol, phenol, catechol, resorcinol, hydroquinone, pentaerythritol, trimethylolethane, trimethylolpropane, a pentose, a hexose, glucose, fructose, sorbitol, sucrose, raffinose, isomers thereof, salts thereof, esters thereof, hydrates thereof, or any mixture thereof, and the rosin oil comprises decarboxylated tall oil rosin acids.

[00105] 36. The wax composition according to any one of paragraphs 30 to 35, wherein: the base wax comprises a reaction product of a dimer fatty acid and an amine or an alcohol, the dimer fatty acid comprises dimerized tall oil fatty acids, the amine comprises the amine comprises ethylamine, ethylenediamine, propylamine, propylenediamine, laurylamine, octadecylamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyethylenepolyamine, ethanolamine, diethanolamine, triethanolamine, piperazine, aminoethylpiperazine, aniline, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, o-xylenediamine, m-xylenediamine, p-xylenediamine, or any mixture thereof, the alcohol comprises stearyl alcohol, palmityl alcohol, myristyl alcohol, ethylene glycol, glycerine, 1,2- propylene glycol, 1,3-propylene glycol, 1,4-butene diol, isomers thereof, salts thereof, esters thereof, hydrates thereof, or any mixture thereof, and the rosin oil comprises decarboxylated tall oil rosin acids.

[00106] 37. The wax composition according to any one of paragraphs 30 to 36, wherein: the base wax comprises a reaction product of an oligomeric acid and an amine or an alcohol, the oligomeric acid comprises monomer tall oil fatty acids and dimerized tall oil fatty acids, the amine comprises the amine comprises ethylamine, ethylenediamine, propylamine, propylenediamine, laurylamine, octadecylamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyethylenepolyamine, ethanolamine, diethanolamine, triethanolamine, piperazine, aminoethylpiperazine, aniline, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, o-xylenediamine, m-xylenediamine, p- xylenediamine, or any mixture thereof, the alcohol comprises stearyl alcohol, palmityl alcohol, myristyl alcohol, ethylene glycol, glycerine, 1,2-propylene glycol, 1,3-propylene glycol, 1,4- butene diol, isomers thereof, salts thereof, esters thereof, hydrates thereof, or any mixture thereof, and the rosin oil comprises decarboxylated tall oil rosin acids.

[00107] 38. The wax composition according to any one of paragraphs 30 to 37, wherein the rosin oil has an acid value of less than 150 mg KOH/g of the rosin oil, as measured according to ASTM D465-15.

[00108] 39. The wax composition according to any one of paragraphs 30 to 38, wherein: the base wax comprises a reaction product of a dimer fatty acid and an amine, and the dimer fatty acid and the rosin oil are produced in situ from a mixture comprising tall oil fatty acids and tall oil rosin acids.

[00109] 40. A wax composition, comprising: a base wax comprising a reaction product of dimerized tall oil fatty acids and an amine comprising the amine comprises ethylamine, ethylenediamine, propylamine, propylenediamine, laurylamine, octadecylamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyethylenepolyamine, ethanolamine, diethanolamine, triethanolamine, piperazine, aminoethylpiperazine, aniline, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, o-xylenediamine, m-xylenediamine, p-xylenediamine, or any mixture thereof, or any mixture thereof; and a rosin oil comprising decarboxylated tall oil rosin acids and less than 25 wt% of rosin acids, wherein the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on a combined weight of the base wax and the rosin oil.

[00110] 41. The wax composition according to paragraph 40, wherein the dimerized tall oil fatty acids and the rosin oil are produced in situ from a mixture comprising tall oil fatty acids and tall oil rosin acids.

[00111] 42. The wax composition according to paragraph 40 or 41, wherein a reaction mixture comprising the dimerized tall oil and the amine is reacted to product the reaction product, and wherein the reaction mixture has a weight ratio of the dimerized tall oil to amine of about 1 : 1 to about 20: 1.

[00112] 43. A method for making a wax composition, comprising: combining a first catalyst and a mixture comprising fatty acids and rosin acids to produce a first mixture, wherein the mixture comprising fatty acids and rosin acids has a first dehydroabietic acid concentration; heating the first mixture to a first temperature that is less than 250°C to produce a first reaction mixture having a second dehydroabietic acid concentration greater than the first dehydroabietic acid concentration; heating the first reaction mixture to a second temperature that is at 250°C or more to produce a second reaction mixture, wherein the second reaction mixture comprises rosin oil, dimer acids, and monomer acids, and has a rosin oil yield of greater than 25%; combining a reagent with the second reaction mixture to produce a third mixture, wherein the reagent comprises an amine, an alcohol, or a mixture thereof; heating the third mixture to a temperature of about 80°C to about 300°C to produce a base wax; and cooling the third mixture comprising the base wax and the rosin oil to a temperature of about 20°C to about 30°C to produce a wax composition, and wherein the wax composition comprises about 5 wt% to about 80 wt% of the rosin oil, based on the combined weight of the base wax and the rosin oil.

[00113] 44. The method according to paragraph 43, further comprising cooling the second reaction mixture to a temperature of about 20°C to about 80°C to provide a cooled second reaction mixture prior to heating combing the reagent with the second reaction mixture to produce the third mixture, and wherein the first catalyst comprises nickel, palladium, platinum, iron, copper, cobalt, manganese, tin, sulfur, iodine, selenium or any combination thereof.

[00114] 45. The method according to paragraph 43 or 44, further comprising combining a second catalyst with the first reaction mixture to produce a second mixture, wherein the second mixture is heated to produce the second reaction mixture, and wherein the second catalyst comprises methanesulfonic acid, p-toluenesulfonic acid, phosphoric acids, orthophosphoric acid, metaphosphoric acid, pyrophosphoric acid, sulfuric acid, isomers thereof, salts thereof, esters thereof, or any mixture thereof.

[00115] 46. The method according to any one of paragraphs 43 to 45, wherein the mixture comprising fatty acids and rosin acids is derived from crude tall oil or distilled tall oil, or a blend thereof.

[00116] 47. The method according to any one of paragraphs 43 to 46, wherein the mixture comprising fatty acids and rosin acids comprises crude tall oil.

[00117] 48. The method according to any one of paragraphs 43 to 47, wherein rosin oil comprises less than 25 wt% of rosin acids.

[00118] 49. The wax composition or the method according to any one of paragraphs 30 to 48, wherein the wax composition has a viscosity of about 1,000 Pa-s to about 28,000 Pa-s at a temperature of about 25°C.

[00119] 50. The wax composition according to any one of paragraphs 33 to 36, 39, or 49, wherein the dimer fatty acids are derived from crude tall oil.

[00120] 51. The wax composition according to any one of paragraphs 33 to 36, 39, or 49, wherein the dimer fatty acids are derived entirely from crude tall oil.

[00121] Certain embodiments and features have been described using a set of numerical upper limits and a set of numerical lower limits. It should be appreciated that ranges including the combination of any two values, e.g., the combination of any lower value with any upper value, the combination of any two lower values, and/or the combination of any two upper values are contemplated unless otherwise indicated. Certain lower limits, upper limits and ranges appear in one or more claims below. All numerical values are "about" or "approximately" the indicated value, and take into account experimental error and variations that would be expected by a person having ordinary skill in the art.

[00122] Various terms have been defined above. To the extent a term used in a claim is not defined above, it should be given the broadest definition persons in the pertinent art have given that term as reflected in at least one printed publication or issued patent. Furthermore, all patents, test procedures, and other documents cited in this application are fully incorporated by reference to the extent such disclosure is not inconsistent with this application and for all jurisdictions in which such incorporation is permitted.

[00123] While the foregoing is directed to embodiments, other and further embodiments of the invention can be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow.