Emulsifier particles and methods for making and using same

1. A method for making emulsifier particles, the method comprising

distilling a liquid composition to produce a molten emulsifier, wherein the liquid composition comprises (1) an alkali metal salt or an alkaline earth metal salt of a carboxylic acid terminated fatty amine condensate, (2) an alkali metal salt or an alkaline earth metal salt of a modified tall oil, or (3) a blend of an alkali metal salt or an alkaline earth metal salt of a carboxylic acid terminated fatty amine condensate and an alkali metal salt or an alkaline earth metal salt of a modified tall oil;

cooling the molten emulsifier to produce an emulsifier solid; and

reducing a size of an emulsifier solid via a mechanical attrition process to produce emulsifier particles having:

a Brunauer/Emmett/Teller (BET) specific surface area of about 0.3 m 2 /g to about 1 m 2 /g,

a BET pore volume of at least 0.001 cm 3 /g to about 0.005 cm 3 /g,

a BET average pore width of about 50 angstroms to about 200 angstroms,

a bulk density of about 0.3 g/cm 3 to about 0.6 g/cm 3 , and

a weight average particle size of about 5 μm to less than 80 μm.

2. The method of claim 1 , wherein the mechanical attrition process includes at least one of: grinding, milling, or a combination of grinding and milling.

3. The method of claim 1 , wherein the liquid includes water.

4. The method of claim 1 , wherein cooling the molten emulsifier to produce the emulsifier solid comprises contacting the molten emulsifier with a substrate having a temperature less than the melting point of the molten emulsifier.

5. The method of claim 1 , wherein the emulsifier particles comprise an alkali metal salt or an alkaline earth metal salt of a modified tall oil and the method further comprises at least one of:

adding an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal oxide, an alkaline earth metal oxide, or any mixture thereof to a modified tall oil, to produce the alkali metal salt or the alkaline earth metal salt of the modified tall oil;

reacting a tall oil distillate component and an unsaturated polycarboxylic acid, a carboxylic anhydride, or a mixture of an unsaturated polycarboxylic acid and a carboxylic anhydride, to produce the modified tall oil; or

a combination thereof.

6. The method of claim 5 , wherein at least one of:

the tall oil distillate component comprises tall oil fatty acids, tall oil rosin acids, or a mixture thereof;

the unsaturated polycarboxylic acid comprises maleic acid, fumaric acid, phthalic acid, trans-2-hexenedioic acid, trans-3-hexenedioic acid, cis-3-octenedioic acid, cis-4-octenedioic acid, trans-3-octenedioic acid, succinic acid, or any mixture thereof;

the carboxylic anhydride comprises maleic anhydride, succinic anhydride, or a mixture thereof; or

a combination thereof.

7. The method of claim 1 , further comprising reacting a tall oil distillate component with maleic anhydride to produce the modified tall oil, wherein the tall oil distillate component comprises tall oil fatty acids, tall oil rosin acids, or a mixture thereof.

8. The method of claim 1 , wherein the emulsifier particles comprise an alkali metal salt or an alkaline earth metal salt of a carboxylic acid terminated fatty amine condensate, and wherein the method further comprises at least one of:

adding an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal oxide, an alkaline earth metal oxide, or any mixture thereof to a carboxylic acid terminated fatty amine condensate, to produce the alkali metal salt or the alkaline earth metal salt of the carboxylic acid terminated fatty amine condensate;

reacting a fatty acid amine condensate and a polycarboxylic acid, a carboxylic anhydride, or a mixture of a polycarboxylic acid and a carboxylic anhydride, to produce the carboxylic acid terminated fatty amine condensate; or

a combination thereof.

9. The method of claim 1 , wherein the emulsifier particles have a BET specific surface area of about 0.5 m 2 /g to about 1 m 2 /g.

10. The method of claim 1 , wherein the emulsifier particles have:

a bulk density of about 0.4 g/cm 3 to about 0.6 g/cm 3 ; and

a BET average pore width of about 50 angstroms to about 150 angstroms.

11. The method of claim 1 , wherein the emulsifier particles have:

a Krumbein roundness of 0.1 to less than 0.8, and

a Krumbein sphericity of 0.1 to less than 0.8.

12. The method of claim 1 , wherein the emulsifier particles have a BET pore volume of at least 0.0012 cm 3 /g to about 0.002 cm 3 /g.

13. The method of claim 1 , wherein the emulsifier particles have an average particle size of less than 54 μm.

14. The method of claim 1 , wherein the emulsifier particles have:

a BET specific surface area of about 0.5 m 2 /g to about 1 m 2 /g;

a BET pore volume of at least 0.0012 cm 3 /g to about 0.003 cm 3 /g; and

a BET average pore width of about 50 angstroms to about 150 angstroms.

15. The method of claim 1 , wherein the emulsifier particles have:

a BET pore volume of at least 0.0012 cm 3 /g to about 0.002 cm 3 /g; and

a BET average pore width of about 50 angstroms to less than 100 angstroms.

16. The emulsifier particles of claim 1 , wherein the emulsifier particles have:

a BET specific surface area of at least 0.5 m 2 /g to about 1 m 2 /g;

a BET pore volume of at least 0.0012 cm 3 /g to about 0.002 cm 3 /g;

a BET average pore width of about 50 angstroms to less than 100 angstroms;

a weight average particle size of about 5 μm to less than 27 μm; and

an average Krumbein roundness of 0 . 1 to 0 . 7 .