WO2019222009A1

WO2019222009A1 - Processes for making phenolic-aldehyde polymer gels and carbon materials produced therefrom

Info

Publication number: WO2019222009A1
Application number: PCT/US2019/031410
Authority: WO
Inventors: Yi Ren; Shahid P. Qureshi
Original assignee: Georgia-Pacific Chemicals Llc
Priority date: 2018-05-14
Filing date: 2019-05-09
Publication date: 2019-11-21

Abstract

Processes for making polymer gels and carbon materials therefrom. In some examples, the process can include reacting a first mixture that can include a first phenolic monomer, a first aldehyde monomer, and a first catalyst to produce a first prepolymer. The process can also include reacting a second mixture that can include a second phenolic monomer, a second aldehyde monomer, and a second catalyst to produce a second prepolymer. The first phenolic monomer and the second phenolic monomer can have different chemical structures and/or the first aldehyde monomer and the second aldehyde monomer can have different chemical structures. The first prepolymer and the second prepolymer can be combined to produce a third mixture. The first prepolymer and the second prepolymer in the third mixture can be polymerized to produce a polymer gel.

Description

PROCESSES FOR MAKING PHENOLIC-ALDEHYDE POLYMER GELS AND CARBON MATERIALS PRODUCED THEREFROM

BACKGROUND

Field

[0001] Embodiments described herein generally relate to processes for making phenolic- aldehyde polymer gels and carbon materials produced therefrom.

Description of the Related Art

[0002] Carbon materials such as carbon aerogels, xerogels, and cryogels have been used in a variety of products, such as supercapacitors, to improve their properties. Such carbon material can be produced by converting polymer gels into the desired carbon material. For example, resorcinol and formaldehyde can be used to make precursor solutions ( e.g ., a "sol," which is a solution or a colloidal dispersion of particles in a liquid), which can then be processed into large monolithic polymer gels or "sol -gels" or polymer particles in gel form by polymerization.

[0003] For many applications, aerogels, which are dried gels having pores with diameters between about 2 nm and 50 nm (mesoporous) or larger, are the preferred end product. The polymer gels, however, are difficult and/or expensive to convert into an aerogel. For example, supercritical drying and/or freeze drying, the drying processes typically used to produce aerogels, requires specialized equipment and is time consuming and expensive.

[0004] There is a need, therefore, for improved processes for making polymer gels and carbon materials, e.g., aerogels, therefrom.

SUMMARY

[0005] Processes for making polymer gels and carbon materials therefrom are provided. In some examples, the process can include reacting a first mixture that can include a first phenolic monomer, a first aldehyde monomer, and a first catalyst to produce a first prepolymer. The process can also include reacting a second mixture that can include a second phenolic monomer, a second aldehyde monomer, and a second catalyst to produce a second prepolymer. The first phenolic monomer and the second phenolic monomer can have different chemical structures and/or the first aldehyde monomer and the second aldehyde monomer can have different chemical structures. The first prepolymer and the second prepolymer can be combined to produce a third mixture. The first prepolymer and the second prepolymer in the third mixture can be polymerized to produce a polymer gel.

[0006] In some examples, the process for making a polymer gel can include reacting a first mixture that can include phenol, formaldehyde, and a first catalyst to produce a first prepolymer. The first catalyst can be or include N,N-d\ ethyl eth an am i n e, N,N- dimethylmethanamine, A'-rn ethyl methanamine, A'-ethyl eth an amine, ethanamine, or any mixture thereof. The process can also include reacting a second mixture that can include resorcinol, formaldehyde, and a second catalyst to produce a second prepolymer. The second catalyst can be or include formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or any mixture thereof. The first prepolymer and the second prepolymer can be combined to produce a third mixture. The third mixture can include about 5 wt% to about 95 wt% of the first prepolymer, based on a combined weight of the first prepolymer and the second prepolymer. The third mixture can be heated at a temperature of about 65°C to about 99°C for a time period of about 5 hours to about 96 hours to produce a polymer gel.

[0007] In some examples, the process for making a carbon material can include reacting a first mixture that can include a first phenolic monomer, a first aldehyde monomer, and a first catalyst to produce a first prepolymer. The process can also include reacting a second mixture that can include a second phenolic monomer, a second aldehyde monomer, and a second catalyst. The first phenolic monomer and the second phenolic monomer can have different chemical structures and/or the first aldehyde monomer and the second aldehyde monomer can have different chemical structures. The first prepolymer and the second prepolymer can be combined to produce a third mixture. The first prepolymer and the second prepolymer in the third mixture can be polymerized to produce a polymer gel. The polymer gel can be heated to produce the carbon material.

DESCRIPTION

[0008] Polymer gels can be produced by polymerizing a mixture that includes at least a first prepolymer and a second prepolymer in a solution, dispersion, suspension, and/or emulsion polymerization process. The polymer gel can be in the form of polymer gel particles and/or polymer gel monolithic structures. The first prepolymer and the second prepolymer can have at least one property that is different from one another. In one example, the first prepolymer can be prepared by reacting a first phenolic monomer and a first aldehyde monomer and the second prepolymer can be prepared by reacting a second phenolic monomer and a second aldehyde monomer, where the first phenolic monomer and the second phenolic monomer have different chemical structures. In another example, the first prepolymer can be prepared by reacting the first phenolic monomer and the first aldehyde monomer and the second prepolymer can be prepared by reacting the second phenolic monomer and the second aldehyde monomer, where the first aldehyde monomer and the second aldehyde monomer have different chemical structures. In another example, the first prepolymer can be prepared by reacting the first phenolic monomer and the first aldehyde monomer and the second prepolymer can be prepared by reacting the second phenolic monomer and the second aldehyde monomer, where the first phenolic monomer and the second phenolic monomer have different chemical structures and the first aldehyde monomer and the second aldehyde monomer have different chemical structures. In another example, the first prepolymer can be prepared by reacting the first phenolic monomer and the first aldehyde monomer and the second prepolymer can be prepared by reacting the second phenolic monomer and the second aldehyde monomer, where the first phenolic monomer and the second phenolic monomer have different chemical structures and the first aldehyde monomer and the second aldehyde monomer have the same chemical structure.

[0009] It has been surprisingly and unexpectedly discovered that polymer gels produced by polymerizing a mixture that includes at least the first prepolymer and the second prepolymer can be processed to produce a carbon material with a high overall carbon yield and/or a high mesopore volume. Illustrative carbon material can be or include, but is not limited to, a pyrolyzed carbon material and an activated carbon material. In some examples, the polymer gel can be processed to produce a pyrolyzed carbon material or activated carbon material having a mesopore volume of about 0.2 cm³/g to about 3 cm³/g. In some examples, the polymer gel can be processed to produce a pyrolyzed carbon material having an overall carbon yield of about 20% to about 40%. In other examples, the polymer gel can be processed to produce a pyrolyzed carbon material having an overall carbon yield of about 5% to about 25%.

[0010] As used herein, the term "micropore" refers to a pore having an average cross- sectional length, e.g ., a diameter, of less than 2 nanometers. As used herein, the term “mesopore” refers to a pore having an average cross-sectional length, e.g. , a diameter, of 2 nanometers to about 50 nanometers. As used herein, the term "macropore" refers to a pore having an average cross-sectional length, e.g ., a diameter, of greater than 50 nanometers.

[0011] The mesopore volume and the micropore volume can be measured by placing the carbon material into a MICROMERITICS^® VacPrep 061, where the carbon material can be placed under vacuum at a temperature of about 300°C to about 400°C for a time period of about 16 hours to about 24 hours. The carbon material can then be loaded into a MICROMERITICS^® TRISTAR^® II device for BET analysis. BET surface area can be provided in the analysis. Mesoporous data can be taken from the BJH Adsorption calculation and Microporous data can be taken from the T-plot micropore report. The combined micropore volume and mesopore volume can be calculated by adding the mesopore volume and the micropore volume. In some examples, the carbon material can be a pyrolyzed carbon material produced by pyrolyzing a cured polymer gel in a GSL1100X or a GSL1700X tube furnace under a nitrogen atmosphere by heating the cured polymer gel over a time period of about 6 hours up to a temperature of about 900°C for about 1 hour and then cooling the pyrolyzed carbon material to room temperature.

[0012] Scanning Electron Microscopy (SEM) can also be used to support the porous nature of the carbon materials. For example, a pyrolyzed or activated carbon material can be examined by both SEM (Hitachi S3400N) and FE SEM (Hitachi SET 8230) to obtain images of the surface topography showing the relative sizes of the meso and micro porosity of the carbon samples. Images can be obtained at magnifications from 500X to 300000X. For bead samples, both the outside surface of the bead and the inner surface, obtained by fracturing the bead, can be examined. The images can be examined to obtain qualitative data on the porosity differences between different pyrolyzed or activated carbon material samples.

[0013] The carbon yield can be measured by measuring the mass of a liquid resin and the remaining mass after the final step, e.g. , pyrolysis or activation, using an analytical balance. The overall percent yield of carbon can be calculated by dividing the mass of the carbon material, e.g. , pyrolyzed or activated carbon material, by the mass of the liquid resin times 100%. Since the exact amount of phenolic monomers, e.g. , phenol and/or resorcinol, used to synthesize phenolic prepolymers is known, the percent yield of carbon with regard to the phenolic monomers can be calculated by dividing the overall percent yield of carbon by the wt% of phenolic compounds used to produce the first prepolymer and the second prepolymer times 100%. For example, if the starting liquid resin mass is lOg, the amount of phenolic monomers used to produce the liquid resin is 50 wt%, and the final carbon mass is 2 g, then the overall percent yield of carbon is 2/10*100% = 20%, and the percent yield of carbon with respect to the phenolic monomers is 20/50*100% = 40%.

[0014] It has also been surprisingly and unexpectedly discovered that polymer gels produced by polymerizing the mixture that includes the first prepolymer and the second prepolymer can be processed to produce the carbon material having the high carbon yield and/or the high mesopore volume without any intermediate drying step, e.g ., without subjecting the polymer gel to freeze drying, solvent exchange, microwave drying, supercritical drying, vacuum drying, heating in a fluidized bed, calcination, superheated steam drying, adiabatic drying, centrifugation, conveyor belt drying, gas drying, or electric drying. In other words, the polymer gels, which can include water, acid, free monomers, and/or other liquids disposed within the pores thereof, can be directly pyrolyzed, activated, or otherwise heated at a temperature sufficient, e.g. , about 600°C to about l,l00°C, and for a time sufficient, e.g. , about 1 minute to about 12 hours, to produce the carbon material, e.g. , a pyrolyzed carbon material and/or an activated carbon material, having the high carbon yield and/or the high mesopore volume.

[0015] The first phenolic monomer, the first aldehyde monomer, and a first catalyst can be mixed, blended, or otherwise combined with one another to produce a mixture or“first mixture”. In some examples, one or more first diluents can be mixed, blended, or otherwise combined with the first phenolic monomer, the first aldehyde monomer, and the first catalyst to produce the first mixture. The first mixture can be reacted to make, form, or otherwise produce the first prepolymer. In some examples, the first phenolic monomer and the first catalyst can be mixed, blended, or otherwise combined with one another to produce an intermediate mixture or“first intermediate mixture”. The first intermediate mixture can be heated at a temperature of about 45°C, about 50°C, or about 55°C to about 70°C, about 75°C, about 80°C, or about 85°C to produce a heated first intermediate mixture. The first aldehyde monomer can be mixed, blended, or otherwise combined with the heated first intermediate mixture to produce the first mixture. The first mixture can be heated at a temperature of about 50°C, about 55°C, or about 60°C to about 75°C, about 80°C, about 85°C, or about 90°C to produce a precursor to the first prepolymer that can have a viscosity of about 40 cP to about 150 cP at a temperature of about 25°C. The precursor to the first prepolymer can have a solids content of about 5 wt%, about 10 wt%, about 20 wt%, about 30 wt%, or about 40 wt% to about 50 wt%, about 60 wt%, about 70 wt%, or more.

[0016] The solids content of the precursor to the first prepolymer can be increased by removing liquid therefrom to produce the first prepolymer. In some examples, the precursor to the first prepolymer can be distilled under a vacuum to produce the first prepolymer having a solids content of about 50 wt%, about 55 wt%, or about 60 wt% to about 75 wt%, about 80 wt%, about 85 wt%, about 95 wt%, or more. In other examples, the precursor to the first prepolymer can be contacted with one or more drying agents and then filtered to remove liquid and the drying agent therefrom to produce the first prepolymer having a solids content of a50 wt%, about 55 wt%, or about 60 wt% to about 75 wt%, about 80 wt%, about 85 wt%, about 95 wt%, or more. Illustrative drying agents can be or include, but are not limited to, sodium sulfate, magnesium sulfate, or a mixture thereof. In some examples, the first prepolymer can have a solids content of at least 50 wt%, at least 55 wt%, at least 60 wt%, at least 65 wt%, at least 70 wt%, at least 75 wt%, or at least 80 wt% to about 83 wt%, about 85 wt%, or about 87 wt%.

[0017] The first mixture can have a molar ratio of the first phenolic monomer to the first aldehyde monomer of about 0.25: 1, about 0.3: 1, about 0.35:1, about 0.4: 1, about 0.45: 1, or about 0.5: 1 to about 0.55: 1, about 0.6:1, about 0.65: 1, about 0.7: 1, about 0.75: 1, about 0.8: 1, about 0.85: 1, about 0.9: 1, about 0.95: 1, or about 1 : 1. For example, the first mixture can have a molar ratio of the first phenolic monomer to the first aldehyde monomer of about 0.25:1 to about 1 : 1, about 0.4: 1 to about 1 : 1, about 0.5: 1 to about 0.8: 1, or about 0.4: 1 to about 0.6: 1.

[0018] The first mixture can include about 55 wt%, about 57 wt%, about 60 wt%, about 63 wt%, or about 65 wt% to about 67 wt%, about 70 wt%, about 72 wt%, about 74 wt%, or about 76 wt% of the first phenolic monomer, based on a combined solids weight of the first phenolic monomer, the first aldehyde monomer, and the first catalyst. In some examples, the first mixture can include about 35 wt%, about 37 wt%, about 40 wt%, about 43 wt%, or about 45 wt% to about 47 wt%, about 50 wt%, about 53 wt%, about 55 wt%, about 57 wt%, about 60 wt%, or more of the first phenolic monomer, based on a combined weight of the first phenolic monomer, the first aldehyde monomer, the first catalyst, and any first diluent.

[0019] The first mixture can include about 0.1 wt%, about 0.5 wt%, about 1 wt%, about 2 wt%, or about 3 wt% to about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, about 10 wt%, or more of the first catalyst, based on a combined solids weight of the first phenolic monomer, the first aldehyde monomer, and the first catalyst. In some examples, the first mixture can include about 0.1 wt%, about 0.3 wt%, about 0.5 wt%, about 0.7 wt%, or about 1 wt% to 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% of the first catalyst, based on a combined weight of the first phenolic monomer, the first aldehyde monomer, the first catalyst, and any first diluent.

[0020] The first mixture can include about 22 wt%, about 25 wt%, about 27 wt%, about 30 wt%, or about 33 wt% to about 35 wt%, about 37 wt%, about 39 wt%, about 41 wt%, about 43 wt%, or more of the first aldehyde monomer, based on a combined solids weight of the first phenolic monomer, the first aldehyde monomer, and the first catalyst. In some examples, the first mixture can include about 15 wt%, about 17 wt%, about 20 wt%, about 23 wt%, or about 25 wt% to about 27 wt%, about 30 wt%, about 33 wt%, about 35 wt%, or about 37 wt% of the first aldehyde monomer, based on a combined weight of the first phenolic monomer, based on a combined weight of the first phenolic monomer, the first aldehyde monomer, the first catalyst, and any first diluent.

[0021] The first mixture can include about 15 wt%, about 17 wt%, about 20 wt%, about 23 wt%, or about 25 wt% to about 27 wt%, about 30 wt%, about 33 wt%, about 35 wt%, or about 37 wt%, or more of the first diluent, based on a combined weight of the first phenolic monomer, the first aldehyde monomer, the first catalyst, and the first diluent. The amount of the first diluent in the first prepolymer, the second prepolymer, or a mixture thereof can be measured by placing about 0.1 g to about 0.2 g of the sample in ACS grade methanol (available from Sigma Aldrich) on a METROHM^® 703 Ti Stand and titrating with a METROHM^® 701 KF TITRINO^® using HYDRANAL® Composite 5 (available from Honeywell Fluka).

[0022] The first prepolymer can have a pH of about 7, about 7.5, about 8, or about 8.5 to about 9, about 9.5, or about 10 at a temperature of about 25°C and a solids content of about 50 wt% to about 80 wt%. The first prepolymer can have a viscosity of about 300 cP, about 400 cP, about 500 cP, about 600 cP, about 700 cP, about 800 cP, about 900 cP, or about 1,000 cP to about 1,100 cP, about 1,200 cP, about 1,300 cP, about 1,400 cP, about 1,500 cP, about 1,600 cP, about 1,700 cP, about 1,800 cP, about 1,900 cP, or about 2,100 cP at a temperature of about 25°C and a solids content of about 50 wt% to about 85 wt%. In some examples, the first prepolymer can have a viscosity of about 300 cP, about 325 cP, about 350 cP, about 375 cP, about 400 cP, about 425 cP, about 450 cP, or about 475 cP to about 550 cP, about 575 cP, about 600 cP, about 625 cP, about 650 cP, about 675 cP, or about 700 cP at a temperature of about 25°C and a solids content of about 50 wt% to about 85 wt%. In some examples, the first prepolymer can have a viscosity of about 300 cP to less than 750 cP, less than 700 cP, less than 675 cP, less than 650 cP, less than 625 cP, less than 600 cP, less than 575 cP, or less than 550 cP at a temperature of about 25°C and a solids content of about 50 wt% to about 85 wt%. The viscosity of the first prepolymer, the second prepolymer, and/or a mixture thereof can be determined by placing a sample in a Brookfield Model DV-II + Viscometer. The viscometer can be allowed to run until the reading is consistent for 5 minutes and the torque is reading between 40-60 %.

[0023] The first prepolymer can have a refractive index of about 1.5200, about 1.5250, about 1.5300, or about 1.5350 to about 1.5400, about 1.5450, about 1.5500, or about 1.5600. In some examples, the first prepolymer can have a refractive index of about 1.5200 to about 1.5600, about 1.5300 to about 1.5500, or about 1.5350 to about 1.5500. The refractive index of the first prepolymer and the second prepolymer can be measured with an Abbemat 200 Anton Paar refractometer. The refractive index measurement procedure can be as follows. The cleanliness of the prism can be checked. If the refractive index reading of distilled water left from the previous refractive index measurement is not 1.3325+/-0.0001, the prism and presser can be cleaned with distilled water, methanol, isopropyl alcohol, or other suitable solvent, and the prism was be refilled with distilled water. The presser can immediately be closed and the refractive index measurement taken. These steps can be repeated if necessary until the refractive index reading of distilled water is l.3325±0.000l . Once the refractive index reading of the distilled water is l.3325±0.000l, any distilled water on the presser can be wiped off. The presser of the refractometer can be lifted and the about 0.5 mL to about 1.0 ml of the sample to be measured can be transferred to the prism with a plastic pipette. For a refractive index measurement, there must be sufficient sample transferred to the prism such that the entire prism area is covered with the sample. The sample can be gently stirred in the prism with the pipet tip to break the surface tension. The presser can be closed and the refractive index measurement can be taken. The temperature displayed by the refractometer should be at 25°C +/- ±0. l°C. The preceding procedure can be repeated until two successive readings equal to or within 0.0001 refractive index units are acquired and the average of those two successive readings is the RI values reported for a given sample. [0024] The first prepolymer can have a weight average molecular weight of about 200 g/mol, about 300 g/mol, about 350 g/mol, about 400 g/mol, or about 450 g/mol to about 500 g/mol, about 550 g/mol, about 600 g/mol, about 650 g/mol, about 700 g/mol, about 1,000 g/mol, about 1,200 g/mol, about 1,500 g/mol, about 1700 g/mol, or about 2000 g/mol. In some examples, the first prepolymer can have a weight average molecular weight of about 300 g/mol to about 700 g/mol, about 400 g/mol to about 600 g/mol, about 500 g/mol to about 600 g/mol, about 500 g/mol to about 550 g/mol, or about 425 g/mol to about 550 g/mol. In some examples, the second prepolymer can have a weight average molecular weight of less than 800 g/mol, less than 750 g/mol, less than 700 g/mol, less than 650 g/mol, less than 600 g/mol, less than 550 g/mol, or less than 500 g/mol.

[0025] The weight average molecular weight of the first prepolymer, the second prepolymer, or a mixture of the first prepolymer and the second prepolymer can be measured via gel permeation chromatography (GPC). A sample of the first prepolymer, the second prepolymer, or a mixture thereof can be solubilized in tetrahydrofuran with 0.5% acetic acid and separated on a series of AGILENT^® PLgel GPC columns. The separated components can be detected via UV absorption at 254nm. Molecular weight averages can be determined using a retention time calibration based on polystyrene standards of known molecular weights.

[0026] The first prepolymer can contain less than 10 wt%, less than 9 wt%, less than 8 wt%, less than 7 wt%, less than 6 wt%, less than 5 wt%, or less than 4 wt% of any free or unreacted first phenolic monomer. The first prepolymer can contain less than 10 wt%, less than 9 wt%, less than 8 wt%, less than 7 wt%, less than 6 wt%, less than 5 wt%, or less than 4 wt% of any free or unreacted first aldehyde monomer. In some examples, the first prepolymer can contain less than 10 wt%, less than 9 wt%, less than 8 wt%, less than 7 wt%, less than 6 wt%, less than 5 wt%, or less than 4 wt% of a combined amount of any free or unreacted first phenolic monomer and any free or unreacted first aldehyde monomer.

[0027] The amount of any free first phenolic monomer and any free first aldehyde monomer in the first prepolymer, the amount of any free second phenolic monomer and any free second aldehyde monomer in the second prepolymer, or a mixture thereof can be determined via ultra-high pressure liquid chromatography (uPLC) using the ACQUITY^® H-Class uPLC sold by Waters Corporation. A sample of the first prepolymer, the second prepolymer, or a mixture thereof can be solubilized in mixtures of acetonitrile, methanol, and water, depending on the analyte of interest. The resulting solutions can be separated using a Cl 8 column with UV detection. The phenolic monomer concentration, e.g ., phenol and resorcinol, can be determined using three point external calibrations with known standards. The aldehyde monomer concentration can be derivatized with 2,4-dinitrophenylhydrazine prior to quantification.

[0028] The second phenolic monomer, the second aldehyde monomer, and a second catalyst can be mixed, blended, or otherwise combined with one another to produce a mixture or “second mixture”. In some examples, one or more additives can be mixed, blended, or otherwise combined with the second phenolic monomer, the second aldehyde monomer, and the second catalyst to produce the second mixture. In some examples, one or more diluents or“second diluents” can be mixed, blended, or otherwise combined with the second phenolic monomer, the second aldehyde monomer, the second catalyst, and, if present, the additive to produce the second mixture.

[0029] The second mixture can be reacted to make, form, or otherwise produce the second prepolymer. In some examples, the second phenolic monomer and the second catalyst can be mixed, blended, or otherwise combined with one another to produce an intermediate mixture or“second intermediate mixture”. In other examples, the second phenolic monomer, the second catalyst, and one or more additives can be mixed, blended, or otherwise combined with one another to produce the second intermediate mixture. The second intermediate mixture can be heated at a temperature of about 30°C, about 35°C, about 40°C, or about 45°C to about 50°C, about 55°C, about 60°C, or about 65°C to produce a heated second intermediate mixture. The second aldehyde monomer can be added to the heated second intermediate mixture to produce the second mixture. In some examples, the second aldehyde monomer can be added all at once, in multiple additions, or in a relatively slow and continuous or semi continuous manner. The second mixture can be heated at a temperature of about 40°C, about 45°C, or about 50°C to about 55°C, about 60°C, or about 65°C for a time period of about 0.5 hours, about 1 hour, about 2 hours, or about 3 hours to about 4 hours, about 5 hours, about 6 hours, about 7 hours, about 8 hours, or more to produce the second prepolymer. The second prepolymer can be cooled, e.g. , to room temperature.

[0030] The second mixture can have a molar ratio of the second phenolic monomer to the second aldehyde monomer of about 0.25: 1, about 0.3:1, about 0.35: 1, about 0.4:1, about 0.45:1, or about 0.5: 1 to about 0.55:1, about 0.6: 1, about 0.65:1, about 0.7: 1, about 0.75: 1, about 0.8: 1, about 0.85: 1, about 0.9:1, about 0.95: 1, or about 1 :1. For example, the second mixture can have a molar ratio of the second phenolic monomer to the second aldehyde monomer of about 0.25: 1 to about 1 : 1, about 0.4: 1 to about 1 : 1, about 0.5: 1 to about 0.8: 1, or about 0.4: 1 to about 0.6: 1.

[0031] The second mixture can include about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, or about 55 wt% to about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, or more of the second phenolic monomer, based on a combined solids weight of the second phenolic monomer, the second aldehyde monomer, and the second catalyst. The second mixture can include about 25 wt%, about 30 wt%, about 35wt%, about 40 wt%, or about 45 wt% to about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, or more of the second phenolic monomer, based on a combined solids weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, and any additive. In some examples, the second mixture can include about 15 wt%, about 17 wt%, about 20 wt%, about 23 wt%, or about 25 wt% to about 27 wt%, about 30 wt%, about 33 wt%, about 35 wt%, or more of the second phenolic monomer, based on a combined weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, any additive, and any second diluent.

[0032] The second mixture can include about 1 wt%, about 3 wt%, about 5 wt%, about 7 wt%, or about 10 wt% to about 15 wt%, about 17 wt%, about 20 wt%, about 23 wt%, about 25 wt%, or more of the second catalyst, based on a combined solids weight of the second phenolic monomer, the second aldehyde monomer, and the second catalyst. The second mixture can include about 0.7 wt%, about 1 wt%, about 2.5 wt%, about 3.5 wt%, or about 5 wt% to about 7 wt%, about 10 wt%, about 13 wt%, about 15 wt%, about 20 wt%, or more of the second catalyst, based on a combined solids weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, and any additive. In some examples, the second mixture can include about 0.5 wt%, about 1 wt%, about 2 wt%, about 3 wt%, or about 4 wt% to about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, or about 10 wt% of the second catalyst, based on a combined weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, any additive, and any second diluent.

[0033] The second mixture can include about 17 wt%, about 20 wt%, about 23 wt%, about 25 wt%, or about 30 wt% to about 35 wt%, about 37 wt%, about 40 wt%, about 43 wt%, about 45 wt%, about 47 wt%, about 49 wt% or more of the second aldehyde monomer, based on a combined solids weight of the second phenolic monomer, the second aldehyde monomer, and the second catalyst. The second mixture can include about 16 wt%, about 18 wt%, about 20 wt%, about 22 wt%, or about 24 wt% to about 26 wt%, about 28 wt%, about 30 wt%, about 33 wt%, about 36 wt%, about 40 wt%, about 43 wt%, about 45 wt%, or more of the second aldehyde monomer, based on a combined solids weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, and any additive. In some examples, the second mixture can include about 15 wt%, about 17 wt%, about 20 wt%, about 23 wt%, or about 25 wt% to about 27 wt%, about 30 wt%, about 33 wt%, about 35 wt%, or about 37 wt% of the second aldehyde monomer, based on a combined weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, any additive, and any second diluent.

[0034] The second mixture can include about 0.1 wt%, about 0.5 wt%, about 1 wt%, about 1.5 wt%, or about 2 wt% to about 3 wt%, about 4 wt%, about 5 wt%, about 5.5 wt%, about 6 wt%, or more of the additive, based on a combined solids weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, and the additive. In some examples, the second mixture can include about 0.1 wt%, about 0.3 wt%, about 0.5 wt%, about 0.7 wt%, or about 1 wt% to about 1.5 wt%, about 1.7 wt%, about 2 wt%, about 2.5 wt%, or about 3 wt% of the additive, based on a combined weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, the additive, and any second diluent. .

[0035] The second mixture can include about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, or about 60 wt% to about 65 wt%, about 67 wt%, about 70 wt%, about 73 wt%, about 75 wt%, or more of the second diluent, based on a combined weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, and the second diluent. The second mixture can include about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, or about 60 wt% to about 65 wt%, about 67 wt%, about 70 wt%, about 73 wt%, about 75 wt%, or more of the second diluent, based on a combined weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, any additive, and the second diluent.

[0036] The second prepolymer can have a pH of about 2, about 2.5, or about 3 to about 3.5, about 4, about 4.5, or about 5 at a temperature of about 25°C and a solids content of about 27 wt% to about 51 wt%. The second prepolymer can have a viscosity of about 5 cP, about 7 cP, about 10 cP, about 13 cP, about 15 cP, about 17 cP, about 20 cP, or about 23 cP to about 25 cP, about 27 cP, about 30 cP, about 35 cP, about 40 cP, about 45 cP, about 50 cP, about 55 cP, about 60 cP, about 65 cP, about 70 cP, about 75 cP, or about 80 cP at a temperature of about 25°C and a solids content of about 27 wt% to about 51 wt%. In some examples, the first prepolymer can have a viscosity of about 10 cP to less than 80 cP, less than 75 cP, less than 60 cP, less than 55 cP, less than 50 cP, less than 45 cP, less than 40 cP, or less than 35 cP at a temperature of about 25°C and a solids content of about 27 wt% to about 51 wt%.

[0037] The second prepolymer can have a refractive index of about 1.4050, about 1.4150, about 1.4200, or about 1.4250 to about 1.4300, about 1.4350, about 1.4400, about 1.4450, about 1.4500, or about 1.4550. In some examples, the second prepolymer can have a refractive index of about 1.405 to about 1.445, about 1.4150 to about 1.4350, about 1.4200 to about 1.4400, or about 1.4200 to about 1.4300.

[0038] The second prepolymer can have a weight average molecular weight of about 200 g/mol, about 300 g/mol, about 350 g/mol, about 400 g/mol, or about 450 g/mol to about 500 g/mol, about 550 g/mol, about 600 g/mol, about 650 g/mol, about 700 g/mol, about 1,000 g/mol, about 1,200 g/mol, about 1,500 g/mol, about 1,700 g/mol, or about 2,000 g/mol. In some examples, the second prepolymer can have a weight average molecular weight of about 300 g/mol to about 700 g/mol, about 400 g/mol to about 600 g/mol, about 500 g/mol to about 600 g/mol, about 500 g/mol to about 550 g/mol, or about 425 g/mol to about 550 g/mol. In some examples, the second prepolymer can have a weight average molecular weight of less than 800 g/mol, less than 750 g/mol, less than 700 g/mol, less than 650 g/mol, less than 600 g/mol, less than 550 g/mol, or less than 500 g/mol.

[0039] The second prepolymer can contain less than 10 wt%, less than 9 wt%, less than 8 wt%, less than 7 wt%, less than 6 wt%, less than 5 wt%, or less than 4 wt% of any free second phenolic monomer. The second prepolymer can contain less than 10 wt%, less than 9 wt%, less than 8 wt%, less than 7 wt%, less than 6 wt%, less than 5 wt%, or less than 4 wt% of any free second aldehyde monomer. In some examples, the second prepolymer can contain less than 10 wt%, less than 9 wt%, less than 8 wt%, less than 7 wt%, less than 6 wt%, less than 5 wt%, or less than 4 wt% of a combined amount of any free second phenolic monomer and any free second aldehyde monomer.

[0040] In some examples, the second prepolymer can have a lower viscosity than the first prepolymer. For example, the first prepolymer can have a viscosity of about 300 cP to about

2,100 cP at a temperature of about 25°C and a solids content of about 50 wt% to about 85 wt% and the second prepolymer can have a viscosity of less than 300 cP, e.g, 5 cP to about 80 cP, at a temperature of about 25°C and a solids content of about 27 wt% to about 51 wt%.

[0041] The first phenolic monomer and the second phenolic monomer can be or include one or more substituted phenolic monomers, one or more unsubstituted phenolic monomers, or any combination or mixture of substituted and/or unsubstituted phenolic monomers. In some examples, the first phenolic monomer and/or the second phenolic monomer can be represented by Formula I:

Formula I

[0042] where R¹ and are R² are independently selected from hydrogen (H), a hydroxy group, a Ci-₅ alkyl, or OR³, where R³ is a C1-5 alkyl or C1-5 aryl, and where at least one of R¹ and R² is a hydroxy group. In other examples, the first phenolic monomer and/or the second phenolic monomer can be represented by Formula II:

Formula II

[0043] where each of R_a, R_b, R_c, and R_d is independently hydrogen (H); a hydroxy group; a halide, e.g . , fluoride, chloride, bromide or iodide; a nitro group; a benzo group; a carboxy group; an acyl group such as formyl, an alkyl-carbonyl, e.g. , acetyl, and an arylcarbonyl, e.g. , benzoyl; an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; an alkenyl such as an unsubstituted or substituted vinyl and allyl; unsubstituted or substituted methacrylate, unsubstituted or substituted acrylate; silyl ether; siloxanyl; aryl such as phenyl and naphthyl; aralkyl such as benzyl; or alkaryl such as alkylphenyls, and where at least two of R_a, R_c, and R_d is hydrogen. [0044] Other suitable phenolic monomers can be or include phenol itself (i.e., mono-hydroxy benzene). Other suitable examples of substituted phenolic monomers can include, but are not limited to, alkyl-substituted phenols such as the cresols and xylenols; cycloalkyl-substituted phenols such as cyclohexyl phenol; alkenyl-substituted phenols; aryl -substituted phenols such as p-phenyl phenol; alkoxy-substituted phenols such as 3,5-dimethyoxyphenol; aryloxy phenols such as p-phenoxy phenol; and halogen-substituted phenols such as p-chlorophenol. Dihydric phenols or dihydroxybenzenes such as catechol, resorcinol, hydroquinone, bisphenol A, bisphenol F, or any mixture thereof. In another example, the phenolic monomer can be or include phenol, resorcinol, phenol, catechol, hydroquinone, pyrogallol, 5- methylresorcinol, 5-ethylresorcinol, 5-propylresorcinol, 4-methylresorcinol, 4- ethylresorcinol, 4-propylresorcinol, resorcinol monobenzoate, resorcinol monosinate, resorcinol diphenyl ether, resorcinol monomethyl ether, resorcinol monoacetate, resorcinol dimethyl ether, phloroglucinol, benzoylresorcinol, resorcinol rosinate, alkyl substituted resorcinol, aralkyl substituted resorcinol, 2-methylresorcinol, phloroglucinol, 1,2,4- benzenetriol, 3,5-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde, 4-ethylresorcinol,

2.5-dimethylresorcinol, 5-methylbenzene-l,2,3-triol, 3,5-dihydroxybenzyl alcohol, 2,4,6- trihydroxytoluene, 4-chlororesorcinol, 2',6'-dihydroxyacetophenone, 2', 4'- dihydroxyacetophenone, 3',5'-dihydroxyacetophenone, 2,4,5-trihydroxybenzaldehyde, 2,3,4- trihydroxybenzaldehyde, 2,4,6-trihydroxybenzaldehyde, 3,5-dihydroxybenzoic acid, 2,4- dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, l,3-dihydroxynaphthalene, 2', 4'- dihydroxypropiophenone, 2',4'-dihydroxy-6'-methylacetophenone, l-(2,6-dihydroxy-3- methylphenyl)ethanone, 3-methyl 3,5-dihydroxybenzoate, methyl 2,4-dihydroxybenzoate, gallacetophenone, 2,4-dihydroxy-3-methylbenzoic acid, 2,6-dihydroxy-4-methylbenzoic acid, methyl 2,6-dihydroxybenzoate, 2-methyl-4-nitroresorcinol, 2,4,5-trihydroxybenzoic acid,

3.4.5-trihydroxybenzoic acid, 2,3,4-trihydroxybenzoic acid, 2,4,6-trihydroxybenzoic acid, 2- nitrophloroglucinol, phloroglucinol, or any mixture thereof. In some examples, the first phenolic monomer and/or the second phenolic monomer that can be used to produce the first prepolymer can be or include, but is not limited to, phenol, benzene-l,3-diol, 2-methylphenol, 3-methylphenol, 4-methylphenol, benzene- 1 ,2-diol, benzene-l,3,5-triol, or any mixture thereof. In other examples, the first phenolic monomer can be or include phenol and the second phenolic monomer can be or include benzene- 1, 3 -diol.

[0045] The first aldehyde monomer and the second aldehyde monomer can be or include one or more substituted aldehyde monomers, one or more unsubstituted aldehyde monomers, or any mixture thereof. Aldehyde monomers suitable for use as the first aldehyde monomer and/or the second aldehyde monomer can be represented by Formula III: R⁴CHO, where R⁴ is hydrogen or a hydrocarbon radical. Illustrative hydrocarbon radicals can include from 1 to about 8 carbon atoms. In another example, the first aldehyde monomer and/or the second aldehyde monomer can be or include a so-called masked aldehyde or aldehyde equivalent, such as acetals or hemiacetals. In some examples, the first aldehyde monomer and/or the second aldehyde monomer can include, but is not limited to, formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, furfuraldehyde, benzaldehyde, or any mixture thereof. One or more other aldehydes, such as glyoxal can be used in place of or in combination with formaldehyde and/or other aldehydes. In at least one example, the first aldehyde monomer and/or the second aldehyde monomer can include formaldehyde, UFC, or any combination or mixture thereof. In some examples, the first aldehyde monomer that can be used to produce the first prepolymer can be or include, but is not limited to, formaldehyde, acetaldehyde, propanal, butanal, furan-2-carbaldehyde, benzaldehyde, (2//)-3 -phenyl prop-2-enal, or any mixture thereof. In other examples the first aldehyde monomer and the second aldehyde monomer can be or include formaldehyde.

[0046] In some examples, the first aldehyde monomer and/or the second aldehyde monomer can be or include, but is not limited to, one or more multifunctional aldehyde compounds. As used herein, the terms "multifunctional aldehyde compound" and "multifunctional aldehyde" are used interchangeably and refer to compounds having at least two functional groups, with at least one of the functional groups being an aldehyde group. For example, the multifunctional aldehyde can include two or more aldehyde functional groups. In another example, the multifunctional aldehyde can include at least one aldehyde functional group and at least one functional group other than an aldehyde functional group. As used herein, the term "functional group" refers to reactive groups in the multifunctional aldehyde compound and can include, but is not limited to, aldehyde groups, carboxylic acid groups, ester groups, amide groups, imine groups, epoxide groups, aziridine groups, azetidinium groups, and hydroxyl groups.

[0047] The multifunctional aldehyde compound can include two or more carbon atoms and have two or more aldehyde functional groups. For example, the multifunctional aldehyde compound can include two, three, four, five, six, or more carbon atoms and have two or more aldehyde functional groups. The multifunctional aldehyde compound can include two or more carbon atoms and have at least one aldehyde functional group and at least one functional group other than an aldehyde group such as a carboxylic acid group, an ester group, an amide group, an imine groups, an epoxide group, an aziridine group, an azetidinium group, and/or a hydroxyl group. For example, the multifunctional aldehyde compound can include two, three, four, five, six, or more carbon atoms and have at least one aldehyde functional group and at least one functional group other than an aldehyde group such as a carboxylic acid group, an ester group, an amide group, an imine groups, an epoxide group, an aziridine group, an azetidinium group, and/or a hydroxyl group.

[0048] Suitable bifunctional or difunctional aldehyde compounds that include three (3) or more carbon atoms and have two aldehyde functional groups (-CHO) can be represented by Formula IV:

Formula IV,

[0049] where R is a divalent aliphatic, cycloaliphatic, aromatic, or heterocyclic group having from 1 to 12 carbon atoms. Illustrative multi-functional aldehydes can include, but are not limited to, malonaldehyde, succinaldehyde, glutaraldehyde, 2-hydroxyglutaraldehyde, b-methylglutaraldehyde, adipaldehyde, pimelaldehyde, suberaldehyde, malealdehyde, fumaraldehyde, sebacaldehyde, phthalaldehyde, isophthalaldehyde, terephthal aldehyde, ring- substituted aromatic aldehydes, or any mixture thereof. A suitable bifunctional or difunctional aldehyde that includes two carbon atoms and has two aldehyde functional groups is glyoxal.

[0050] Illustrative multifunctional aldehyde compounds that include an aldehyde group and a functional group other than an aldehyde group can include, but are not limited to, glyoxylic acid, glyoxylic acid esters, glyoxylic acid amides, 5-(hydroxymethyl)furfural, or any mixture thereof. The aldehyde group in the multifunctional aldehyde compound can exist in other forms, e.g ., as a hydrate. As such, any form or derivative of a particular multifunctional aldehyde compound can be used to prepare the binder compositions discussed and described herein. For example, in the context of glyoxylic acid, glyoxylic acid, glyoxylic acid monohydrate, and/or glyoxylate can be combined with the tannins and the Lewis acid to produce the binder composition. [0051] Illustrative first catalysts that can be used to produce the first prepolymer can be or include, but are not limited to, N,N-d\ ethyl ethana i ne, N,N-d\ m ethy 1 m eth an am i n e, A- methylmethanamine, A-eth y 1 eth an am i n e, ethanamine, or any mixture thereof. Illustrative second catalysts that can be used to produce the second prepolymer can be or include, but are not limited to, formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or any mixture thereof. Illustrative additives that can be used to produce the second prepolymer can be or include, but are not limited to, ammonium formate, ammonium ethanoate, ammonium propanoate, diammonium malonate, ammonium citrate, or any mixture thereof.

[0052] Illustrative diluents that can be used to produce the first prepolymer (first diluent) and/or the second prepolymer (second diluent) can be or include, but are not limited to, water, one or more alcohols, one or more ketones, one or more glycols, or any mixture thereof. Illustrative alcohols can be or include, but are not limited to, methanol, ethanol, propanol, isopropanol, butanol, or any mixture thereof. Illustrative glycols can be or include, but are not limited to, ethylene glycol, propylene glycol, or a mixture thereof. Illustrative ketones can be or include, but are not limited to, acetone, acetylacetone, cyclohexanone, or any mixture thereof. In some examples, the diluents can also include porogens/surfactants such as P 123 (EO20PO20EO20), Fluronic 127, or a mixture thereof that are commercially available from Sigma Aldrich.

[0053] In some examples, the first phenolic monomer, the first aldehyde monomer, the first catalyst, the second phenolic monomer, the second aldehyde monomer, the second catalyst, and/or the additive can be neat, i.e., undiluted, or can be mixed with the first diluent or the second diluent. For example, the first aldehyde monomer can be in the form of an aqueous solution, suspension, or dispersion. In one example, the first aldehyde monomer can be an aqueous solution of formaldehyde, e.g ., a 37 wt% or 50 wt% aqueous formaldehyde solution. In some examples, aqueous solutions of the different components, e.g. , the first aldehyde, can also include additional diluents, e.g. , methanol.

[0054] The first prepolymer and the second prepolymer can be mixed, blended, or otherwise combined with one another to produce a mixture or“third mixture”. The third mixture can have any desired weight ratio of the first prepolymer to the second prepolymer. For example, the third mixture can include about 1 wt%, about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 40 wt%, or about 45 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%, about 95 wt%, or about 99 wt% of the first prepolymer, based on a combined weight of the first prepolymer and the second prepolymer. In another example, the third mixture can include about lwt%, about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 40 wt%, or about 45 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%, about 95 wt%, or about 99 wt% of the first prepolymer, based on a combined weight of the first prepolymer, any free first phenolic monomer, any free first aldehyde monomer, the first catalyst, any free second phenolic monomer, any free second aldehyde monomer, the second catalyst, any additive, any first diluent, any second diluent, any water produced during the synthesis of the first prepolymer, and any water produced during the synthesis of the second prepolymer. In another example, the third mixture can include about 1 wt%, about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 40 wt%, or about 45 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%, about 95 wt%, or about 99 wt% of the first prepolymer, based on a total weight of the third mixture.

[0055] The first prepolymer and the second prepolymer in the third mixture can be polymerized to produce the polymer gel. Polymerizing the third mixture can produce a cured polymer. As used herein, the terms“cured” and "curing" refer to the toughening or hardening of polymers via an increased degree of crosslinking of polymer chains. Crosslinking refers to the structural and/or morphological change that occurs in the first prepolymer and the second prepolymer, such as by covalent chemical reaction, ionic interaction or clustering, phase transformation or inversion, and/or hydrogen bonding.

[0056] In some examples, the third mixture can be heated at produce the polymer gel. For example, the third mixture can be heated, e.g ., in an oven, at a temperature of about 65°C, about 67°C, about 70°C, about 73°C, about 75°C, about 77°C, or about 80°C to about 83°C, about 85°C, about 87°C, about 90°C, about 93°C, about 95°C, about 97°C, or about 99°C to produce the polymer gel. In some examples, the third mixture can be heated at a temperature of about 65°C to about 99°C for a time period of about 5 hours, about 10 hours, about 15 hours, about 20 hours, or about 24 hours to about 30 hours, about 36 hours, about 42 hours, about 48 hours, about 72 hours, about 96 hours, or longer to produce the polymer gel. In some examples, the third mixture can be heated under any desired atmosphere, e.g, air, nitrogen, oxygen, argon, or any mixture thereof.

[0057] Alternatively or in addition to heating the third mixture, catalytic curing can be used to at least partially cure the third mixture. In one example, the catalytic curing of the third mixture can include the addition of one or more acid catalysts. Illustrative acid catalysts can be or include, but are not limited to, one or more ammonium salts, formic acid, propanic acid, oxalic acid, maleic acid, maleic anhydride, or any mixture thereof. Illustrative ammonium salts can be or include, but are not limited to, ammonium sulfate, ammonium chloride, or a mixture thereof.

[0058] As used herein, the term "polymer gel" refers to a network of polymer chains that have one or more pores or voids therein, and a liquid at least partially occupies or fills the one or more pores or voids. As used herein, the term "dried polymer gel" refers to a network of polymer chains having one or more pores or voids therein, and a gas at least partially occupies or fills the one or more pores or voids. If the liquid that at least partially occupies or fills the voids is water, the polymer gel can be referred to as a "hydrogel polymer." In some examples, the polymer gel can include about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, or about 50 wt% to about 55 wt%, about 60 wt%, about 70 wt%, about 80 wt%, about 90 wt%, or about 100 wt% of a liquid disposed within the pores or voids therein, based on a solids weight of the polymer gel. In other examples, the polymer gel can include at least 40 wt%, at least 45 wt%, at least 50 wt%, or at least 52 wt% to about 55 wt%, about 60 wt%, about 65 wt%, or about 70 wt% of the liquid disposed within the pores or voids therein, based on a solids weight of the polymer gel. The liquid disposed within the pores or voids of the polymer gel can be or include, but is not limited to, the first diluent, the second diluent, water produced during the synthesis of the first prepolymer, water produced during the synthesis of the second prepolymer, water produced during curing of the third mixture to produce the polymer gel, or any mixture thereof.

[0059] In some examples, the third mixture can be in the form of a solution and the polymer gel produced by curing the third mixture can be in the form of a monolithic structure, e.g. , the shape of the reaction vessel the third mixture is cured in. The monolithic polymer gel can be processed to produce a pyrolyzed carbon material and/or an activated carbon material. In some examples, the monolithic polymer gel can be ground, milled, or otherwise mechanically disrupted or converted into a plurality of polymer gel particles and the plurality of polymer gel particles can be processed to produce the pyrolyzed carbon material and/or the activated carbon material. In other examples, the monolithic polymer gel can be processed to produce the pyrolyzed carbon material and/or the activated carbon material and the pyrolyzed carbon material and/or the activated carbon material can be ground, milled, or otherwise mechanically disrupted or converted into a plurality of pyrolyzed carbon particles and/or activated carbon particles.

[0060] In some examples, the third mixture can be in the form of a suspension, dispersion, or emulsion and the polymer gel produced by curing the third mixture can be in the form of particles, i.e., polymer particles in gel form. For example, one or more carrier fluids can be mixed, blended, combined, or otherwise contacted with the first prepolymer and the second prepolymer to produce a third mixture in the form of a dispersion, suspension, and/or emulsion.

[0061] As used herein, the term "carrier fluid" refers to any suitable liquid medium or mixture of liquid mediums capable of suspending, dispersing, or otherwise distributing droplets of the third mixture therein. For example, a suspension, dispersion, emulsion, or other distributed mixture of the carrier fluid and the third liquid can be produced. In some examples, the carrier fluid can be or include one or more hydrocarbons, water, or mixture thereof. Illustrative carrier fluids can be or include, but are not limited to, one or more paraffinic oils, one or more naphthenic oils, one or more aromatic oils, one or more plant based or plant derived oils, one or more chlorinated hydrocarbons, water, or any mixture thereof. Illustrative paraffinic oils can include one or more alkanes having from about 15 to about 40 carbon atoms. Illustrative naphthenic oils can be hydrocarbons based on cycloalkanes. Illustrative cycloalkanes can include, but are not limited to cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, or any combination or mixture thereof. Illustrative plant based or plant derived oils can include, but are not limited to, such as linseed (flaxseed) oil, castor oil, lung oil, soybean oil, cottonseed oil, olive oil, canola oil, corn oil, sunflower seed oil, peanut oil, coconut oil, safflower oil, palm oil, vegetable oil, or any mixture thereof. Suitable commercially available vegetable oils can include, but are not limited to, those sold under the tradename WESSON® and sold by CONAGRA FOODS®, such as the vegetable oil, canola oil, corn oil, blended oils, and the like. Illustrative chlorinated hydrocarbons can include, but are not limited to, carbon tetrachloride, chloroform, methylene chloride, or any mixture thereof. Any type of water can be used as the carrier fluid or to make-up at least a portion of the carrier fluid. For example, the water can be distilled water, deionized water, or a combination or mixture thereof. In another example, the water can be tap water.

[0062] As used herein, the terms "suspension process," "suspension polymerization process," "dispersion process," and "dispersion polymerization process" are used interchangeably and refer to a heterogeneous polymerization process that uses mechanical agitation to mix the reaction mixture in the carrier or "continuous phase" fluid such as a hydrocarbon and/or water, where the reaction mixture phase and the carrier or continuous phase fluid are not miscible. The reaction mixture can be suspended or dispersed in the carrier fluid or continuous phase as droplets, where the first prepolymer and second prepolymer undergo polymerization to form polymer particles in gel form.

[0063] As used herein, the terms "emulsion process" and "emulsion polymerization process" refer to both "normal" emulsions and "inverse" emulsions. Emulsions differ from suspensions in one or more aspects. One difference is that an emulsion will usually include the use of a surfactant that creates or forms the emulsions (small size droplets). When the carrier or continuous phase fluid is a hydrophilic fluid such as water and the reaction mixture phase is a hydrophobic compound(s), normal emulsions ( e.g ., oil -in-water) form, where droplets of the first prepolymer, the second prepolymer, or the first prepolymer and the second prepolymer are emulsified with the aid of a surfactant in the carrier or continuous phase fluid. The monomers and/or prepolymer react in these small size droplets. These droplets are typically small in size as the particles are stopped from coagulating with each other because each particle is surrounded by the surfactant and the charge on the surfactant electrostatically repels other particles. Whereas suspension polymerization usually creates much larger particles than those made with emulsion polymerization. When the carrier or continuous phase fluid is a hydrophobic fluid such as oil and the reaction mixture phase is hydrophilic compounds, inverse-emulsions (e.g., water-in-oil) form.

[0064] If the third mixture is processed to produce polymer particles in gel form, the polymer particles in gel form can have any desired average cross-sectional length. For example, the polymer particles in gel form can have an average cross-sectional length of about 0.001 mm, about 0.01 mm, about 0.1 mm, about 0. 5 mm, or about 1 mm to about 1.5 mm, about 2 mm, about 2.5 mm, about 3 mm, about 3.5 mm, about 4 mm, about 4.5 mm, about 5 mm, about 5.5 mm, about 6 mm, or more. [0065] In some examples, the third mixture and the polymer gel produced therefrom can contain little or no metal ions, e.g ., sodium, iron, lithium, phosphorus, aluminum, arsenic, boron, potassium, or any combination or mixture thereof. The third mixture and the polymer gel form can have a concentration of one or more metal atoms, one or more metal ions, or a combination or mixture of one or more metal atoms and one or more metal ions of less than about 1 wt%, less than about 0.5 wt%, less than about 0.3 wt%, less than about 0.2 wt%, less than about 0.1 wt%, less than about 0.7 wt%, less than about 0.05 wt%, less than about 0.3 wt%, less than about 0.01 wt%, less than about 0.007 wt%, less than about 0.005 wt%, less than about 0.003 wt%, less than about 0.001 wt%, less than about 0.0007 wt%, or less than about 0.0005 wt%, based on a total weight of the third mixture and/or the polymer gel. Similarly, the pyrolyzed and/or activated carbon material produced from the polymer gel can have a concentration of one or more metal atoms, one or more metal ions, or a combination or mixture of one or more metal atoms and one or more metal ions of less than about 1 wt%, less than about 0.5 wt%, less than about 0.3 wt%, less than about 0.2 wt%, less than about 0.1 wt%, less than about 0.7 wt%, less than about 0.05 wt%, less than about 0.3 wt%, less than about 0.01 wt%, less than about 0.007 wt%, less than about 0.005 wt%, less than about 0.003 wt%, less than about 0.001 wt%, less than about 0.0007 wt%, or less than about 0.0005 wt%, based on a total weight of pyrolyzed carbon material or activated carbon material.

[0066] In some examples, metal atoms and/or metal ions can also be intentionally doped or added to the third mixture, the first prepolymer, the second prepolymer, the first mixture, and/or the second mixture to produce a polymer gel that contains or otherwise includes metal atoms and/or metal ions. Nitrogen can also be intentionally doped or added to the third mixture, the first prepolymer, the second prepolymer, the first mixture, and/or the second mixture to produce a polymer gel that contains or otherwise includes nitrogen. Adding or increasing the concentration of nitrogen in the polymer gel can improve the capacitance of one or more end products, e.g. , the pyrolyzed carbon material and/or the activated carbon material. Illustrative nitrogen sources can include, but are not limited to, urea, melamine, nitric acid, or any combination or mixture thereof.

[0067] As noted above, it has surprisingly and unexpectedly discovered that polymer gels produced by polymerizing a mixture that includes the first prepolymer and the second prepolymer can be processed to produce the carbon material, e.g. , a pyrolyzed carbon material and/or an activated carbon material, having the high carbon yield and/or the high mesopore volume without an intermediate drying step. Any pyrolyzation and/or activation process can be used. In one example, the polymer gel can be placed into an oven, a rotary kiln, or other heating apparatus and heated therein. The pyrolysis process can be carried out under an inert atmospheres, e.g ., a nitrogen, argon, or other inert gas or gas mixture. Pyrolysis and activation processes are well known to those skilled in the art.

[0068] The duration of the pyrolysis, i.e., the period of time during which the polymer particles can be maintained at the elevated temperature, can be about 30 seconds, about 1 minute, about 5 minutes, about 10 minutes, about 30 minutes, about 45 minutes, or about 1 hour to about 2 hours, about 3 hours, about 5 hours, about 7 hours, about 10 hours, or longer. The pyrolysis dwell temperature can be about 600°C, about 700°C, about 800°C, or about 850°C to about 950°C, about l,000°C, about l,l00°C, about l,200°C, about l,500°C, or about l,800°C.

[0069] The pyrolyzed carbon material can have a micropore volume of less than 0.3 cm³/g, less than 0.27 cm³/g, less than 0.25 cm³/g, less than 0.23 cm³/g, less than 0.22 cm³/g, less than 0.21 cm³/g, less than 0.2 cm³/g, less than 0.19 cm³/g, or less than 0.18 cm³/g. In some examples, the pyrolyzed carbon material can have a micropore volume of about 0.05 cm³/g, about 0.07 cm³/g, about 0.1 cm³/g, about 0.12 cm³/g, or about 0.14 cm³/g to about 0.16 cm³/g, about 0.18 cm³/g, about 0.2 cm³/g, about 0.22 cm³/g, about 0.24 cm³/g, about 0.26 cm³/g, or about 0.28 cm³/g. It should be understood that the pyrolyzed carbon material that can have a micropore volume of less than 0.3 cm³/g, e.g. , from about 0.05 cm³/g to about 0.28 cm³/g, can be produced directly from the polymer gel and not from a dried polymer gel.

[0070] The pyrolyzed carbon material can have a mesopore volume of about 0.2 cm³/g, about 0.3 cm³/g, about 0.4 cm³/g, or about 0.5 cm³/g to about 0.7 cm³/g, about 1 cm³/g, about 1.3 cm³/g, about 1.5 cm³/g, about 1.8 cm³/g, about 2 cm³/g, about 2.3 cm³/g, about 2.5 cm³/g, about 2.8 cm³/g, or about 3 cm³/g. In some examples, the pyrolyzed carbon material can have a mesopore volume of about 0.2 cm³/g, about 0.25 cm³/g, about 0.3 cm³/g, about 0.35 cm³/g, about 0.4 cm³/g, about 0.45 cm³/g, about 0.5 cm³/g, or about 0.55 cm³/g to about 0.6 cm³/g, about 0.65 cm³/g, about 0.7 cm³/g, about 0.75 cm³/g, about 0.8 cm³/g, about 0.9 cm³/g, about 0.95 cm³/g, about 1 cm³/g, about 1.05 cm³/g, about 1.1 cm³/g, about 1.15 cm³/g, about 1.2 cm³/g, about 1.25 cm³/g, or about 1.3 cm³/g. In some examples, the pyrolyzed carbon material can have a mesopore volume of at least 0.2 cm³/g, at least 0.25 cm³/g, at least 0.3 cm³/g, at least 0.35 cm³/g, at least 0.4 cm³/g, at least 0.45 cm³/g, or at least 0.5 cm³/g to about 0.6 cm³/g, about 0.65 cm³/g, about 0.7 cm³/g, about 0.75 cm³/g, about 0.8 cm³/g, about 0.9 cm³/g, about 0.95 cm³/g, about 1 cm³/g, about 1.05 cm³/g, about 1.1 cm³/g, about 1.15 cm³/g, about 1.2 cm³/g, about 1.25 cm³/g, or about 1.3 cm³/g. It should be understood that the pyrolyzed carbon material that can have a mesopore volume of about 0.2 cm³/g to about 3 cm³/g, can be produced directly from the polymer gel and not from a dried polymer gel.

[0071] The pyrolyzed carbon material can have a combined micropore volume and mesopore volume of about 0.35 cm³/g, about 0.4 cm³/g, about 0.43 cm³/g, about 0.45 cm³/g, about 0.47 cm³/g, about 0.5 cm³/g, about 0.53 cm³/g, or about 0.55 cm³/g to about 0.6 cm³/g, about 0.63 cm³/g, about 0.65 cm³/g, about 0.67 cm³/g, about 0.7 cm³/g, about 0.73 cm³/g, about 0.75 cm³/g, about 0.8 cm³/g, or about 3.3 cm³/g.

[0072] The pyrolyzed carbon material can have surface area of about 600 m²/g, about 625 m²/g, about 650 m²/g, about 675 m²/g, about 700 m²/g, about 725 m²/g, or about 750 m²/g to about 800 m²/g, about 825 m²/g, about 850 m²/g, about 875 m²/g, about 900 m²/g, about 925 m²/g, about 950 m²/g, about 975 m²/g, about 1,000 m²/g, or greater.

[0073] The pyrolyzed carbon material can have an overall carbon yield of about 15%, about 17%, about 20%, about 23%, about 25%, about 27%, or about 30% to about 33%, about 35%, about 37%, or about 40%. In some examples, the pyrolyzed carbon material can have an overall carbon yield of at least 19%, at least 20%, at least 21%, at least 22%, at least 23%, at least 24%, at least 25%, at least 26%, at least 27%, or at least 28%.

[0074] In some examples, the pyrolyzed carbon material can be activated. Activating the pyrolyzed carbon material can include any activation process or combination of activation processes. In some examples, the pyrolyzed carbon product can be activated by contacting the pyrolyzed carbon material with one or more activating agents. Illustrative activating agents can be or include, but are not limited to, gases such as carbon dioxide, steam, oxygen, or any mixture thereof. Other activating agents can include other compounds or chemicals. The activation process can be from about 1 minute to about 2 days, about 5 minutes to about 1 day, about 1 minute to about 18 hours, about 1 minute to about 12 hours, about 5 minutes to about 8 hours, about 1 minute to about 10 minutes, or about 1 hour to about 5 hours. The pyrolyzed carbon can be heated at a temperature of about 800°C to about l,300°C, about 900°C to about l,050°C, or about 900°C to about l,000°C to produce the activated carbon material. [0075] In one example of an activation process, the pyrolyzed carbon material can be weighed and placed in a rotary kiln and an automated gas control manifold and controller can be set to ramp rate of about 20°C per minute. Carbon dioxide can be introduced to the kiln environment for a period of time once the proper activation temperature has been reached. After activation has occurred, the carbon dioxide can be replaced by nitrogen and the kiln can be cooled down. The recovered activated carbon material can be weighed at the end of the process to assess the level of activation. Suitable activation temperatures can be from about 800°C to about l,300°C, about 900°C to about l,050°C, or about 900°C to about l,000°C. It should be understood that other activation temperatures, either lower or higher, can be employed.

[0076] In some examples, the polymer gel can be processed to produce an activated carbon material. For example, the polymer gel can be contacted with one or more activating agents. Illustrative activating agents can be or include, but are not limited to, gases such as carbon dioxide, steam, oxygen, or any mixture thereof. Other activating agents can include other compounds or chemicals. The activation process can be from about 1 minute to about 2 days, about 5 minutes to about 1 day, about 1 minute to about 18 hours, about 1 minute to about 12 hours, about 5 minutes to about 8 hours, about 1 minute to about 10 minutes, or about 1 hour to about 5 hours. The polymer gel can be heated at a temperature of about 800°C to about l,300°C, about 900°C to about l,050°C, or about 900°C to about l,000°C to produce an activated carbon material. In some examples, the polymer gel can be contacted with nitrogen gas initially and then with carbon dioxide or other activating gas while heated to produce the activated carbon material.

[0077] The degree of activation can be measured in terms of the mass percent of the pyrolyzed carbon material that is lost during the activation step. The degree of activation can be from a low of about 1%, about 5%, about 10%, about 20%, about 30%, about 40%, or about 50% to a high of about 60%, about 70%, about 80%, about 90%, about 95%, or about 99%.

[0078] The activated carbon material can have a micropore volume of less than 0.3 cm³/g, less than 0.27 cm³/g, less than 0.25 cm³/g, less than 0.23 cm³/g, less than 0.22 cm³/g, less than 0.21 cm³/g, less than 0.2 cm³/g, less than 0.19 cm³/g, or less than 0.18 cm³/g. In some examples, the activated carbon material can have a micropore volume of about 0.05 cm³/g, about 0.07 cm³/g, about 0.1 cm³/g, about 0.12 cm³/g, or about 0.14 cm³/g to about 0.16 cm³/g, about 0.18 cm³/g, about 0.2 cm³/g, about 0.22 cm³/g, about 0.24 cm³/g, about 0.26 cm³/g, or about 0.28 cm³/g.

[0079] The activated carbon material can have a mesopore volume of about 0.5 cm³/g, about 0.6 cm³/g, about 0.7 cm³/g, about 0.8 cm³/g, about 0.9 cm³/g, or about 1 cm³/g to about 1.2 cm³/g, about 1.4 cm³/g, about 1.6 cm³/g, about 1.8 cm³/g, about 2 cm³/g, about 2.3 cm³/g, about 2.5 cm³/g, about 2.7 cm³/g, about 3 cm³/g, about 3.3 cm³/g, about 3.5 cm³/g, about 3.7 cm³/g, or about 4 cm³/g. The activated carbon material can have a mesopore volume of about 0.5 cm³/g, about 0.6 cm³/g, about 0.65 cm³/g, about 0.7 cm³/g, about 0.75 cm³/g, 0.8 cm³/g, about 0.85 cm³/g, about 0.9 cm³/g, about 0.95 cm³/g, or about 1 cm³/g to about 1.1 cm³/g, about 1.15 cm³/g, about 1.2 cm³/g, about 1.25 cm³/g, about 1.3 cm³/g, about 1.35 cm³/g, about 1.4 cm³/g, about 1.45 cm³/g, about 1.5 cm³/g, about 1.55 cm³/g, about 1.6 cm³/g, about 1.65 cm³/g, or about 1.7 cm³/g.

[0080] The activated carbon material can have a combined micropore volume and mesopore volume of about 0.6 cm³/g, about 0.7 cm³/g, about 0.8 cm³/g, about 0.9 cm³/g, about 1 cm³/g, about 1.2 cm³/g, about 1.4 cm³/g, or about 1.6 cm³/g to about 2 cm³/g, about 2.5 cm³/g, about 3 cm³/g, about 3.3 cm³/g, about 3.5 cm³/g, about 3.7 cm³/g, about 4 cm³/g, about 4.2 cm³/g, or about 4.3 cm³/g.

[0081] The activated carbon material can have surface area of about 600 m²/g, about 650 m²/g, about 700 m²/g, about 750 m²/g, about 800 m²/g, about 850 m²/g, or about 900 m²/g to about 1,000 m²/g, about 1, 100 m²/g, about 1,200 m²/g, about 1,300 m²/g, about 1,400 m²/g, about 1,500 m²/g, about 1,600 m²/g, about 1,700 m²/g, or greater.

[0082] The activated carbon material can have an overall carbon yield of about 5%, about 10%, about 13%, or about 15% to about 17%, about 20%, about 23%, or about 25%. In some examples, the activated carbon material can have an overall carbon yield of at least 5%, at least 7%, at least 9%, at least 11%, at least 13%, at least 15%, at least 17%, at least 19%, at least 21%, or at least 22%.

Examples

[0083] In order to provide a better understanding of the foregoing discussion, the following non-limiting examples are offered. Although the examples may be directed to specific embodiments, they are not to be viewed as limiting the invention in any specific respect. All parts, proportions, and percentages are by weight unless otherwise indicated. Example 1 - First Prepolymer

[0084] A mixture of phenol and formaldehyde was reacted to produce a first prepolymer. The first prepolymer had a viscosity of about 529 cP at a temperature of about 25°C, a weight average molecular weight of about 558 g/mol, a free first formaldehyde content of about 4.4 wt%, and a free phenol content of about 3.97 wt%.

Example 2 - Second Prepolymer

[0085] A mixture of resorcinol and formaldehyde was reacted to produce a second prepolymer. The second prepolymer had a viscosity of about 12 cP at a temperature of about 25°C, a weight average molecular weight of about 510 g/mol, a free formaldehyde content of about 7.7 wt%, and a free resorcinol content of about 600 ppm.

Examples 3-5 - Preparation of Polymer Gels

[0086] Example 3: about 25 g of the first prepolymer made in Example 1 and about 75 g of the second prepolymer made in Example 2 were mixed in a beaker with stirring for about 5 minutes to produce a mixture that included about 25 wt% of the first prepolymer and about 75 wt% of the second prepolymer.

[0087] Example 4: about 50 g of the first prepolymer made in Example 1 and about 50 g of the second prepolymer made in Example 2 were mixed in a beaker with stirring for about 5 minutes to produce a mixture that included about 50 wt% of the first prepolymer and about 50 wt% of the second prepolymer. The mixture of the first prepolymer and the second prepolymer had a weight average molecular weight of about 576 g/mol, a free formaldehyde content of about 0.6 wt%, a free resorcinol content of about 2.7 wt%, and a free phenol content of about 2.6 wt%. The mixture of the first prepolymer and the second prepolymer had a heat of reaction of about 91 J/g and an onset cure temperature of about 92°C.

[0088] Example 5: about 75 g of the first prepolymer made in Example 1 and about 25 g of the second prepolymer made in Example 2 were mixed in a beaker with stirring for about 5 minutes to produce a mixture that included about 75 wt% of the first prepolymer and about 25 wt% of the second prepolymer.

[0089] For each of Examples 3-5, the mixtures of the first prepolymer and the second prepolymer were polymerized at a temperature of about 95°C to produce polymer gels. The polymer gels were then heated under an atmosphere of nitrogen to a temperature of about

900°C over a time period of about 6 hours and held at 900°C for about 1 hour and then cooled to room temperature to produce a pyrolyzed carbon material. Some properties of the pyrolyzed carbon materials are shown in Table 1 below.

** The combined wt% of P (phenol) and R (resorcinol) in the blend was 44.4%

(PF/RF=75/25), 38.2% (PF/RF=50/50), and 32.0% (PF/RF=25/75), respectively.

[0090] Comparing samples 3-5, sample 4, the 50/50 blend, had a high overall percent yield and percent yield of carbon with regard to phenol and resorcinol without any significant compromise to the mesopore volume.

[0091] Example 6: about 5 g of the first prepolymer made in Example 1 and about 5 g of the second prepolymer made in Example 2 were mixed in a beaker and stirred for about 5 minutes to produce a mixture that included about 50 wt% of the first prepolymer and about 50 wt% of the second prepolymer. The mixture was placed into a 20 mL scintillation vial and the vial was placed in an oven heated at a temperature of about 80°C for about 24 hours to produce a polymer gel.

[0092] Examples 7-10: four samples of the polymer gel were processed into pyrolyzed carbon materials. Prior to pyrolyzing the polymer gels, the mixture of the first prepolymer and the second prepolymer were subjected to different process conditions, which are outlined in Table 2 below “r.t” refers to the length of time the mixture of the first prepolymer and the second prepolymer were kept at room temperature, i.e., 0, 2, or 4 days at room temperature,“ld 80°C” refers to 1 day heated at 80°C to produce the polymer gels, and FD refers to freeze drying. The polymer gels were heated under an atmosphere of nitrogen to a temperature of about 900°C over a time period of about 6 hours and held at 900°C for about 1 hour and then cooled to room temperature to produce a pyrolyzed carbon material. Some properties of the pyrolyzed carbon materials are shown in Table 2 below.

[0093] Table 2 illustrates that these blends are stable at room temperature for at least four days prior to thermal curing, as the final properties are comparable with each other after pyrolysis.

[0094] Examples 11-14: two samples of the second prepolymer made in Example 2 (Examples 11 and 12) and two samples that included a mixture of about 50 wt% of the first prepolymer made in Example 1 and about 50 wt% of the second prepolymer made in example 2 were prepared (Examples 13 and 14). Examples 11-14 were each heated at a temperature of about 80°C for about 24 hours to produce polymer gels. Examples 11 and 13 were not subjected to freeze drying, whereas Examples 12 and 14 were subjected to freeze drying. The polymer gel and freeze dried polymer gels were heated under an atmosphere of nitrogen to a temperature of about 900°C over a time period of about 6 hours and held at 900°C for about 1 hour and then cooled to room temperature to produce a pyrolyzed carbon material. Some properties of the pyrolyzed carbon materials are shown in Table 3 below.

[0095] As shown in Table 3, samples prepared using only the second prepolymer had a significant decrease in mesopore volume and surface area if the pyrolyzed carbon material was produced without freeze-drying. In direct contrast, samples prepared with both the first prepolymer and the second prepolymer had comparable mesopore volume and surface area with and without freeze-drying.

[0096] Examples 15 and 16: two samples of the first prepolymer made in Example 1 were prepared by adding more acid catalyst to accelerate thermal curing. Example 15 and 16 were composed of 43.9 wt% of the prepolymer made in Example 1, 2.2 wt% of maleic anhydride, 1.3 wt% of citric acid, and 52.6 wt% of acetic acid. Each sample was heated at a temperature of about 80°C for about 24 hours to produce polymer gels. Example 15 were not subjected to freeze drying, whereas Example 16 was subjected to freeze drying. The polymer gel and freeze dried polymer gels were heated under an atmosphere of nitrogen to a temperature of about 900°C over a time period of about 6 hours and held at 900°C for about 1 hour and then cooled to room temperature to produce a pyrolyzed carbon material. Some properties of the pyrolyzed carbon materials are shown in Table 3 below.

[0097] Similar to the blended samples, carbon generated from the first prepolymer with and without freeze-drying step showed comparable pore properties.

[0098] Embodiments of the present disclosure further relate to any one or more of the following paragraphs:

[0099] 1. A process for making a polymer gel, comprising: reacting a first mixture comprising a first phenolic monomer, a first aldehyde monomer, and a first catalyst to produce a first prepolymer; reacting a second mixture comprising a second phenolic monomer, a second aldehyde monomer, and a second catalyst to produce a second prepolymer, wherein (1) the first phenolic monomer and the second phenolic monomer have different chemical structures, (2) the first aldehyde monomer and the second aldehyde monomer have different chemical structures, or (3) the first phenolic monomer and the second phenolic monomer have different chemical structures and the first aldehyde monomer and the second aldehyde monomer have different chemical structures; combining the first prepolymer and the second prepolymer to produce a third mixture; and polymerizing the first prepolymer and the second prepolymer in the third mixture to produce a polymer gel.

[00100] 2. A process for making a carbon material, comprising: reacting a first mixture comprising a first phenolic monomer, a first aldehyde monomer, and a first catalyst to produce a first prepolymer; reacting a second mixture comprising a second phenolic monomer, a second aldehyde monomer, and a second catalyst, wherein (1) the first phenolic monomer and the second phenolic monomer have different chemical structures, (2) the first aldehyde monomer and the second aldehyde monomer have different chemical structures, or (3) the first phenolic monomer and the second phenolic monomer have different chemical structures and the first aldehyde monomer and the second aldehyde monomer have different chemical structures; combining the first prepolymer and the second prepolymer to produce a third mixture; polymerizing the first prepolymer and the second prepolymer in the third mixture to produce a polymer gel; and heating the polymer gel to produce the carbon material.

[00101] 3. The process according to paragraph 1 or 2, wherein the first phenolic monomer comprises phenol, benzene- 1, 3 -diol, 2-methylphenol, 3-methylphenol, 4-methylphenol, benzene- 1 ,2-diol, benzene-l,3,5-triol, or a mixture thereof.

[00102] 4. The process according to any one of paragraphs 1 to 3, wherein the first aldehyde monomer comprises formaldehyde, acetaldehyde, propanal, butanal, furan-2-carbaldehyde, benzaldehyde, (2£)-3-phenylprop-2-enal, or a mixture thereof.

[00103] 5. The process according to any one of paragraphs 1 to 4, wherein the first catalyst comprises N,N-d\ ethyl ethana i ne, N,N-d\ m eth y 1 m eth an am i n e, A -m eth y 1 m eth an am i n e, N- ethylethanamine, ethanamine, or a mixture thereof.

[00104] 6. The process according to any one of paragraphs 1 to 5, wherein the second phenolic monomer comprises phenol, benzene- 1,3 -diol, 2-methylphenol, 3-methylphenol, 4- methylphenol, benzene- 1 ,2-diol, benzene-l,3,5-triol, or a mixture thereof. [00105] 7. The process according to any one of paragraphs 1 to 6, wherein the second aldehyde monomer comprises formaldehyde, acetaldehyde, propanal, butanal, furan-2- carbaldehyde, benzaldehyde, (2/',^’)-3 -phenyl prop-2-enal, or a mixture thereof.

[00106] 8. The process according to any one of paragraphs 1 to 7, wherein the second catalyst comprises formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or a mixture thereof.

[00107] 9. The process according to paragraph 1 or 2 of claim 1, wherein: the first phenolic monomer comprises phenol, the first aldehyde monomer comprises formaldehyde, the first catalyst comprises A^f, A-di ethy 1 eth an am i n e, N,N-d\ m ethyl m eth an am i n e, N- methylmethanamine, A'-ethyl eth an amine, ethanamine, or a mixture thereof, the second phenolic monomer comprises benzene-l,3-diol, the second aldehyde monomer comprises formaldehyde, and the second catalyst comprises formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or a mixture thereof.

[00108] 10. The process according to paragraph 1 or 2, wherein the second mixture further comprises an additive.

[00109] 11. The process according to paragraph 10, wherein the first phenolic monomer comprises phenol, benzene- 1, 3 -diol, 2-methylphenol, 3-methylphenol, 4-methylphenol, benzene- 1 ,2-diol, benzene-l,3,5-triol, or a mixture thereof.

[00110] 12. The process according to paragraph 10 or 11, wherein the first aldehyde monomer comprises formaldehyde, acetaldehyde, propanal, butanal, furan-2-carbaldehyde, benzaldehyde, (2£)-3-phenylprop-2-enal, or a mixture thereof.

[00111] 13. The process according to any one of paragraphs 10 to 12, wherein the first catalyst comprises A^f, A-di ethy 1 eth an am i n e, N,N-d\ m ethyl m eth an am i n e, N- methylmethanamine, A'-ethyl ethanamine, ethanamine, or a mixture thereof.

[00112] 14. The process according to any one of paragraphs 10 to 13, wherein the second phenolic monomer comprises phenol, benzene- 1,3 -diol, 2-methylphenol, 3-methylphenol, 4- methylphenol, benzene- 1 ,2-diol, benzene-l,3,5-triol, or a mixture thereof,

[00113] 15. The process according to any one of paragraphs 10 to 14, wherein the second aldehyde monomer comprises formaldehyde, acetaldehyde, propanal, butanal, furan-2- carbaldehyde, benzaldehyde, (2//)-3 -phenyl prop-2-enal, or a mixture thereof. [00114] 16. The process according to any one of paragraphs 10 to 15, wherein the second catalyst comprises formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or a mixture thereof.

[00115] 17. The process according to any one of paragraphs 10 to 16, wherein the additive comprises ammonium formate, ammonium ethanoate, ammonium propanoate, diammonium malonate, ammonium citrate, or a mixture thereof.

[00116] 18. The process according to paragraph 1 or 2, wherein the second mixture further comprises an additive, and wherein: the first phenolic monomer comprises phenol, the first aldehyde monomer comprises formaldehyde, the first catalyst comprises NN- diethylethanamine, N,N-d\ m ethy 1 m eth an am i n e, A^f-m ethyl methanamine, A-ethylethanamine, ethanamine, or a mixture thereof, the second phenolic monomer comprises benzene- 1, 3 -diol, the second aldehyde monomer comprises formaldehyde, the second catalyst comprises formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or a mixture thereof, and the additive comprises ammonium formate, ammonium ethanoate, ammonium propanoate, diammonium malonate, ammonium citrate, or a mixture thereof.

[00117] 19. The process according to paragraph 1 or 2, wherein the second mixture further comprises an additive, and wherein: the first phenolic monomer comprises phenol, the first aldehyde monomer comprises formaldehyde, the second phenolic monomer comprises benzene-l,3-diol, the second aldehyde monomer comprises formaldehyde, and the additive comprises ammonium formate, ammonium ethanoate, ammonium propanoate, diammonium malonate, ammonium citrate, or a mixture thereof.

[00118] 20. The process according to any one of paragraphs 1 to 19, wherein the first prepolymer has a molar ratio of the first phenolic monomer to the first aldehyde monomer of about 0.25: 1 to about 1 : 1, and wherein the second prepolymer has a molar ratio of the second phenolic monomer to the second aldehyde monomer of about 0.25 : 1 to about 1 : 1.

[00119] 21. The process according to any one of paragraphs 1 to 19, wherein the first prepolymer has a molar ratio of the first phenolic monomer to the first aldehyde monomer of about 0.4:1 to about 1 :1, and wherein the second prepolymer has a molar ratio of the second phenolic monomer to the second aldehyde monomer of about 0.4: 1 to about 1 : 1. [00120] 22. The process according to any one of paragraphs 1 to 21, wherein the third mixture comprises about 5 wt% to about 95 wt% of the first prepolymer, based on a combined solids weight of the first prepolymer and the second prepolymer.

[00121] 23. The process according to any one of paragraphs 1 to 21, wherein the third mixture comprises about 20 wt% to about 80 wt% of the first prepolymer, based on a combined solids weight of the first prepolymer and the second prepolymer.

[00122] 24. The process according to any one of paragraphs 1 to 23, wherein the first prepolymer has a refractive index of about 1.5200 to about 1.5600.

[00123] 25. The process according to any one of paragraphs 1 to 24, wherein the second prepolymer has a refractive index of about 1.4050 to about 1.4450.

[00124] 26. The process according to any one of paragraphs 1 to 23, wherein the first prepolymer has a refractive index of about 1.5300 to about 1.5500, and wherein the second prepolymer has a refractive index of about 1.4150 to about 1.4350.

[00125] 27. The process according to any one of paragraphs 1 to 25, wherein the first prepolymer has a viscosity of about 300 cP to about 700 cP at a temperature of about 25°C and a solids content of about 50 wt% to about 85 wt%.

[00126] 28. The process according to any one of paragraphs 1 to 27, wherein the second prepolymer has a viscosity of about 10 cP to about 50 cP at a temperature of about 25°C and a solids content of about 20 wt% to about 70 wt%.

[00127] 29. The process according to any one of paragraphs 1 to 28, wherein the first prepolymer has a weight average molecular weight of about 300 g/mol to about 700 g/mol.

[00128] 30. The process according to any one of paragraphs 1 to 29, wherein the second prepolymer has a weight average molecular weight of about 300 g/mol to about 700 g/mol.

[00129] 31. The process according to any one of paragraphs 1 to 30, wherein the first prepolymer has a free phenol monomer content of less than 10 wt% and a free aldehyde monomer content of less than 10 wt%, based on a solids weight of the first phenolic monomer, the first aldehyde monomer, the first catalyst, and the first prepolymer, and wherein the second prepolymer has a free second phenolic monomer content of less than 10 wt% and a free second aldehyde monomer content of less than 10 wt%, based on a solids weight of the second phenolic monomer, the second aldehyde monomer, the second catalyst, and the second prepolymer.

[00130] 32. The process according to any one of paragraphs 1 to 31, further comprising combining a carrier fluid with the first prepolymer and the second prepolymer to produce the third mixture.

[00131] 33. The process according to paragraph 32, wherein the third mixture is an emulsion, and wherein the carrier fluid is the continuous phase of the emulsion.

[00132] 34. The process according to paragraph 32 or 33, wherein the carrier fluid comprises a mineral oil, a vegetable oil, or a mixture thereof.

[00133] 35. The process according to any one of paragraphs 32 to 34, wherein the polymer gel is in a particulate form having an average cross-sectional length of about 100 pm to about 5 mm.

[00134] 36. The process according to any one of paragraphs 1 to 35, wherein polymerizing the first prepolymer and the second prepolymer in the third mixture to produce the polymer gel comprises heating third mixture at a temperature of about 65°C to about 99°C for a time period of about 5 hours to about 96 hours.

[00135] 37. The process according to any one of paragraphs 2 to 36, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a micropore volume of less than 0.3 cm³/g, a mesopore volume of 0.2 to about 3 cm³/g, and a combined micropore volume and mesopore volume of about 0.3 cm³/g to about 3.25 cm³/g.

[00136] 38. The process according to any one of paragraphs 2 to 36, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a micropore volume of less than 0.3 cm³/g, a mesopore volume of 0.2 to about 1.2 cm³/g, and a combined micropore volume and mesopore volume of about 0.3 cm³/g to about 1.45 cm³/g.

[00137] 39. The process according to any one of paragraphs 2 to 38, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a micropore volume of less than 0.25 cm³/g, a mesopore volume of about 0.25 cm³/g to about 1.1 cm³/g, and a combined micropore volume and mesopore volume of about 0.4 cm³/g to about 1.3 cm³/g. [00138] 40. The process according to any one of paragraphs 2 to 38, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a micropore volume of 0.2 cm³/g or less, a mesopore volume of about 0.4 cm³/g to about 1 cm³/g, and a combined micropore volume and mesopore volume of about 0.5 cm³/g to about 1.3 cm³/g.

[00139] 41. The process according to any one of paragraphs 2 to 38, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a micropore volume of about 0.2 cm³/g or less, a mesopore volume of at least 0.45 cm³/g to about 0.8 cm³/g, and a combined micropore volume and mesopore volume of at least 0.6 cm³/g to about 1.3 cm³/g.

[00140] 42. The process according to any one of paragraphs 2 to 41, wherein the carbon material is produced without subjecting the polymer gel to freeze drying, solvent exchange, microwave drying, supercritical drying, vacuum drying, heating in a fluidized bed, calcination, superheated steam drying, adiabatic drying, centrifugation, conveyor belt drying, gas drying, or electric drying.

[00141] 43. The process according to any one of paragraphs 2 to 42, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a surface area of about 600 m²/g to about 900 m²/g.

[00142] 44. The process according to any one of paragraphs 2 to 43, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material is produced at an overall carbon percent yield of about 20% to about 40%.

[00143] 45. The process according to any one of paragraphs 2 to 43, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material is produced at an overall carbon percent yield of about 25% to about 40%.

[00144] 46. The process according to any one of paragraphs 2 to 45, wherein the polymer gel is heated at a temperature of about 850°C to about 950°C for a time period of about 1 hour to about 8 hours in an atmosphere comprising nitrogen to produce the carbon material. [00145] 47. A process for making a polymer gel, comprising: reacting a first mixture comprising phenol, formaldehyde, and, a first catalyst comprising to produce a first prepolymer, wherein the first catalyst comprises first catalyst comprising NN- diethylethanamine, A^f, A'-di m ethy 1 m eth an am i n e, A^f-m ethyl methanamine, A-ethylethanamine, ethanamine, or a mixture thereof; reacting a second mixture comprising a resorcinol, formaldehyde, and a second catalyst to produce a second prepolymer, wherein the second catalyst comprises formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or a mixture thereof; combining the first prepolymer and the second prepolymer to produce a third mixture, wherein the third mixture comprises about 5 wt% to about 95 wt% of the first prepolymer, based on a combined weight of the first prepolymer and the second prepolymer; and heating third mixture at a temperature of about 65°C to about 99°C for a time period of about 5 hours to about 96 hours to produce a polymer gel.

[00146] 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.

[00147] 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.

[00148] While the foregoing is directed to embodiments of the present invention, other and further embodiments of the invention may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow.

Claims

Claims: What is claimed is:

1. A process for making a polymer gel, comprising:

reacting a first mixture comprising a first phenolic monomer, a first aldehyde monomer, and a first catalyst to produce a first prepolymer;

reacting a second mixture comprising a second phenolic monomer, a second aldehyde monomer, and a second catalyst to produce a second prepolymer, wherein (1) the first phenolic monomer and the second phenolic monomer have different chemical structures, (2) the first aldehyde monomer and the second aldehyde monomer have different chemical structures, or (3) the first phenolic monomer and the second phenolic monomer have different chemical structures and the first aldehyde monomer and the second aldehyde monomer have different chemical structures;

combining the first prepolymer and the second prepolymer to produce a third mixture; and

polymerizing the first prepolymer and the second prepolymer in the third mixture to produce a polymer gel.

2. The process of claim 1, wherein:

the first phenolic monomer comprises phenol, benzene-l,3-diol, 2-methylphenol, 3- methylphenol, 4-methylphenol, benzene- 1 ,2-diol, benzene-l,3,5-triol, or a mixture thereof, the first aldehyde monomer comprises formaldehyde, acetaldehyde, propanal, butanal, furan-2-carbaldehyde, benzaldehyde, (2/',^’)-3 -phenyl prop-2-enal, or a mixture thereof,

the first catalyst comprises A, A-di ethyl ethana i ne, A, A-di m ethy 1 m eth an am i n e, N- methylmethanamine, A-ethylethanamine, ethanamine, or a mixture thereof,

the second phenolic monomer comprises phenol, benzene-l,3-diol, 2-methylphenol, 3-methylphenol, 4-methylphenol, benzene- 1 ,2-diol, benzene-l,3,5-triol, or a mixture thereof, the second aldehyde monomer comprises formaldehyde, acetaldehyde, propanal, butanal, furan-2-carbaldehyde, benzaldehyde, (2/',^’)-3 -phenyl prop-2-enal, or a mixture thereof, and

the second catalyst comprises formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or a mixture thereof.

3. The process of claim 1, wherein the second mixture further comprises an additive, and wherein:

the first catalyst comprises N, A-di ethy 1 eth an am i n e, A^f, A-di m ethy 1 m eth an am i n e, N- methylmethanamine, A'-ethylethanamine, ethanamine, or a mixture thereof,

the second phenolic monomer comprises phenol, benzene- 1, 3 -diol, 2-methylphenol, 3-methylphenol, 4-methylphenol, benzene- 1 ,2-diol, benzene-l,3,5-triol, or a mixture thereof, the second aldehyde monomer comprises formaldehyde, acetaldehyde, propanal, butanal, furan-2-carbaldehyde, benzaldehyde, (2£)-3 -phenyl prop-2-enal, or a mixture thereof, the second catalyst comprises formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or a mixture thereof, and

the additive comprises ammonium formate, ammonium ethanoate, ammonium propanoate, diammonium malonate, ammonium citrate, or a mixture thereof.

4. The process of claim 1, wherein the first prepolymer has a molar ratio of the first phenolic monomer to the first aldehyde monomer of about 0.25:1 to about 1 : 1, and wherein the second prepolymer has a molar ratio of the second phenolic monomer to the second aldehyde monomer of about 0.25 : 1 to about 1 : 1.

5. The process of claim 1, wherein the third mixture comprises about 5 wt% to about 95 wt% of the first prepolymer, based on a combined solids weight of the first prepolymer and the second prepolymer.

6. The process of claim 1, wherein the first prepolymer has a refractive index of about 1.5200 to about 1.5600, and wherein the second prepolymer has a refractive index of about 1.4050 to about 1.4450.

7. The process of claim 1, wherein the first prepolymer has a viscosity of about 300 cP to about 700 cP at a temperature of about 25°C and a solids content of about 50 wt% to about 85 wt%, and wherein the second prepolymer has a viscosity of about 10 cP to about 50 cP at a temperature of about 25°C and a solids content of about 20 wt% to about 70 wt%.

8. The process of claim 1, wherein the first prepolymer has a weight average molecular weight of about 300 g/mol to about 700 g/mol, and wherein the second prepolymer has a weight average molecular weight of about 300 g/mol to about 700 g/mol.

9. The process of claim 1, wherein polymerizing the first prepolymer and the second prepolymer in the third mixture to produce the polymer gel comprises heating third mixture at a temperature of about 65°C to about 99°C for a time period of about 5 hours to about 96 hours.

10. The process of claim 1, wherein:

the first prepolymer has a molar ratio of the first phenolic monomer to the first aldehyde monomer of about 0.25: 1 to about 1 : 1,

the second prepolymer has a molar ratio of the second phenolic monomer to the second aldehyde monomer of about 0.25: 1 to about 1 : 1,

the first prepolymer has a refractive index of about 1.5200 to about 1.5600, the second prepolymer has a refractive index of about 1.4050 to about 1.4450, the first prepolymer has a viscosity of about 300 cP to about 700 cP at a temperature of about 25°C and a solids content of about 50 wt% to about 85 wt%,

the second prepolymer has a viscosity of about 10 cP to about 50 cP at a temperature of about 25°C and a solids content of about 20 wt% to about 70 wt%,

the first prepolymer has a weight average molecular weight of about 300 g/mol to about 700 g/mol,

the second prepolymer has a weight average molecular weight of about 300 g/mol to about 700 g/mol, and

the third mixture comprises about 5 wt% to about 95 wt% of the first prepolymer, based on a combined solids weight of the first prepolymer and the second prepolymer.

11. The process according to claim 1, wherein the second mixture further comprises an additive, and wherein: the first phenolic monomer comprises phenol, benzene-l,3-diol, 2- methylphenol, 3-methylphenol, 4-methylphenol, benzene- 1 ,2-diol, benzene-l,3,5- triol, or a mixture thereof,

the first aldehyde monomer comprises formaldehyde, acetaldehyde, propanal, butanal, furan-2-carbaldehyde, benzaldehyde, (2//)-3 -phenyl prop-2-enal, or a mixture thereof,

the first catalyst comprises N,N-d\ ethyl ethana i ne, N,N- dimethylmethanamine, A'-rn ethyl methanamine, A'-ethyleth an amine, ethanamine, or a mixture thereof,

the second phenolic monomer comprises phenol, benzene- 1, 3 -diol, 2- methylphenol, 3-methylphenol, 4-methylphenol, benzene- 1 ,2-diol, benzene-l,3,5- triol, or a mixture thereof,

the second aldehyde monomer comprises formaldehyde, acetaldehyde, propanal, butanal, furan-2-carbaldehyde, benzaldehyde, (2//)-3 -phenyl prop-2-enal, or a mixture thereof,

the second catalyst comprises formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or a mixture thereof,

the additive comprises ammonium formate, ammonium ethanoate, ammonium propanoate, diammonium malonate, ammonium citrate, or a mixture thereof,

the first prepolymer has a refractive index of about 1.5200 to about 1.5600, the second prepolymer has a refractive index of about 1.4050 to about 1.4450, the first prepolymer has a viscosity of about 300 cP to about 700 cP at a temperature of about 25°C and a solids content of about 50 wt% to about 85 wt%, the second prepolymer has a viscosity of about 10 cP to about 50 cP at a temperature of about 25°C and a solids content of about 20 wt% to about 70 wt%, the first prepolymer has a weight average molecular weight of about 300 g/mol to about 700 g/mol,

the second prepolymer has a weight average molecular weight of about 300 g/mol to about 700 g/mol, and the third mixture comprises about 5 wt% to about 95 wt% of the first prepolymer, based on a combined solids weight of the first prepolymer and the second prepolymer.

12. A process for making a polymer gel, comprising:

reacting a first mixture comprising phenol, formaldehyde, and, a first catalyst comprising to produce a first prepolymer, wherein the first catalyst comprises first catalyst comprising N,N-d\ ethyl ethana i ne, A^f, A- di m et h y 1 m et h an am i n e , A-m eth yl m eth an am i n e, N- ethylethanamine, ethanamine, or a mixture thereof;

reacting a second mixture comprising a resorcinol, formaldehyde, and a second catalyst to produce a second prepolymer, wherein the second catalyst comprises formic acid, acetic acid, propanoic acid, oxalic acid, propanedioic acid, citric acid, malonic acid, or a mixture thereof;

combining the first prepolymer and the second prepolymer to produce a third mixture, wherein the third mixture comprises about 5 wt% to about 95 wt% of the first prepolymer, based on a combined weight of the first prepolymer and the second prepolymer; and

heating third mixture at a temperature of about 65°C to about 99°C for a time period of about 5 hours to about 96 hours to produce a polymer gel.

13. A process for making a carbon material, comprising:

reacting a second mixture comprising a second phenolic monomer, a second aldehyde monomer, and a second catalyst, wherein (1) the first phenolic monomer and the second phenolic monomer have different chemical structures, (2) the first aldehyde monomer and the second aldehyde monomer have different chemical structures, or (3) the first phenolic monomer and the second phenolic monomer have different chemical structures and the first aldehyde monomer and the second aldehyde monomer have different chemical structures; combining the first prepolymer and the second prepolymer to produce a third mixture; polymerizing the first prepolymer and the second prepolymer in the third mixture to produce a polymer gel; and

heating the polymer gel to produce the carbon material.

14. The process of claim 13, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a micropore volume of less than 0.3 cm³/g, a mesopore volume of 0.2 to about 3 cm³/g, and a combined micropore volume and mesopore volume of about 0.3 cm³/g to about 3.25 cm³/g.

15. The process of claim 13, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a micropore volume of 0.2 cm³/g or less, a mesopore volume of about 0.4 cm³/g to about 1 cm³/g, and a combined micropore volume and mesopore volume of about 0.5 cm³/g to about 1.3 cm³/g.

16. The process of claim 13, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a surface area of about 600 m²/g to about 900 m²/g.

17. The process of claim 13, wherein the carbon material is produced without subjecting the polymer gel to freeze drying, solvent exchange, microwave drying, supercritical drying, vacuum drying, heating in a fluidized bed, calcination, superheated steam drying, adiabatic drying, centrifugation, conveyor belt drying, gas drying, or electric drying.

18. The process of claim 13, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material has a micropore volume of less than 0.3 cm³/g, a mesopore volume of 0.2 to about 3 cm³/g, and combined micropore volume and mesopore volume of about 0.3 cm³/g to about 3.25 cm³/g.

19. The process of claim 13, wherein the carbon material is a pyrolyzed carbon material produced by heating the polymer gel in an inert gas, and wherein the pyrolyzed carbon material is produced at an overall carbon percent yield of about 20% to about 40%.

20. The process of claim 12, wherein the polymer gel is heated at a temperature of about 850°C to about 950°C for a time period of about 1 hour to about 8 hours in an atmosphere comprising nitrogen.