KURTH TODD L (US)
TABATABAEE HASSAN ALI (US)
US4073759A | 1978-02-14 | |||
US5045576A | 1991-09-03 | |||
US20150361323A1 | 2015-12-17 | |||
US20110190530A1 | 2011-08-04 |
CLAIMS What is claimed is: 1. A cationic latex emulsion comprising: latex particles; an aqueous liquid emulsified with the latex particles; and a cationic surfactant having the structure: , wherein at each occurrence R2 is independently chosen from substituted or unsubstituted linear or branched (C1-C6)alkyl, substituted or unsubstituted linear or branched (C1-C6)alkenyl, substituted or unsubstituted (C4-C10)cycloalkyl or (C4-C10)cycloalkenyl, substituted or substituted or unsubstituted (C1-C10)alkoxy (for example (C1-C10)alkyl alcohol, (C1-C10)alkyl ether or (C1-C10)alkoxyalcohol), and substituted or unsubstituted (C4-C10)aryl, or wherein R2 together with another R2 forms a substituted or unsubstituted aliphatic or aromatic (C4- C12)heterocycle together with the nitrogen to which they are attached; at each occurrence R3 is independently chosen from substituted or unsubstituted linear or branched (C1-C6)alkyl, substituted or unsubstituted linear or branched (C1-C6)alkenyl, substituted or unsubstituted (C4-C10)cycloalkyl or (C4-C10)cycloalkenyl, substituted or unsubstituted (C1-C10)alkoxy (for example, (C1-C10)alkyl alcohol, (C1-C10)alkyl ether or (C1- C10)alkoxyalcohol), and substituted or unsubstituted (C4-C10)aryl, or wherein R3 together with another R3 forms a substituted or unsubstituted aliphatic or aromatic (C4-C12)heterocycle together with the nitrogen to which they are attached; at each occurrence X- is independently chosen from an anion; RA is chosen from a substituted or unsubstituted (C4-C22)alkyl, a substituted or unsubstituted (C4-C22)alkenyl, and R1 is chosen from a substituted or unsubstituted (C4-C22)alkyl and a substituted or unsubstituted (C4-C22)alkenyl, wherein R1 is optionally modified, the modification comprising maleic anhydride modification, polymerization, ene-reaction modified, hydrogenation, isomerization, branching, or a combination thereof; A is -NH- or -O-; E is -CH2-, -((C2-C4)alkoxy)n3-, or -O-; n1 is an integer that is 0 to 9, for example 1; n2 is an integer that is 0 to 9, for example 1; n1 + n2 is 1 to 10; and n3 is an integer that is 1 to 40. 2. The cationic latex emulsion of claim 1, wherein: at each occurrence R2 is independently chosen from substituted or unsubstituted (C1- C6)alkyl; at each occurrence R3 is independently chosen from substituted or unsubstituted (C1- C6)alkyl; at each occurrence X- is independently chosen from an anion; RA is chosen from a substituted or unsubstituted (C4-C22)alkyl, a substituted or unsubstituted (C4-C22)alkenyl, and ; R1 is chosen from a substituted or unsubstituted (C4-C22)alkyl and a substituted or unsubstituted (C4-C22)alkenyl, wherein R1 is optionally modified, the modification comprising maleic anhydride modification, polymerization, ene-reaction modified, hydrogenation, isomerization, branching, or a combination thereof; A is -NH- or -O-; and n is 1 to 10, for example 1. 3. The cationic latex emulsion of claim 1, wherein R1 is derived from a bio-based fatty acid source. 4. The cationic latex emulsion of claim 1, wherein R1 is unmodified. 5. The cationic latex emulsion of claim 1, wherein R1 is modified, the modification comprising maleic anhydride modification, ene-reaction modified, hydrogenation, isomerization, polymerization, branching, or a combination thereof. 6. The cationic latex emulsion of claim 1, wherein the cationic surfactant has the structure: . 7. The cationic latex emulsion of claim 1, wherein the cationic surfactant has the structure: , wherein R4 is chosen from a substituted or unsubstituted (C4-C22)alkyl and a substituted or unsubstituted (C4-C22)alkenyl, wherein R4 is optionally modified, the modification comprising maleic anhydride modification, polymerization, ene-reaction modified, hydrogenation, isomerization, branching, or a combination thereof. 8. The cationic latex emulsion of claim 1, wherein the cationic latex emulsion comprises 0.1% to 20% of the cationic surfactant by weight of the latex particles. 9. A method of forming the cationic latex emulsion of claim 1, the method comprising: combining an anionic latex emulsion with the cationic surfactant, the anionic latex emulsion comprising the latex particles, and the aqueous liquid emulsified with the latex particles; and agitating the combination of the anionic latex emulsion and the cationic surfactant to form the cationic latex emulsion of claim 1. 10. The method of claim 9, wherein agitating comprises agitating the combination of the anionic latex emulsion and the cationic surfactant to increase the viscosity thereof until said viscosity becomes stable. 11. The method of claim 9, wherein the cationic surfactant is combined with the anionic latex emulsion as a solution of the cationic surfactant in a solvent. 12. The method of claim 11, further comprising: reacting HOC(O)-R1 with a compound having the structure to provide a terminal amine having the structure acidifying the terminal amine to provide an ammonium salt; treating the ammonium salt with an epihalohydrin to provide a gamma hydroxy haloammonium salt; and treating the gamma hydroxy haloammonium salt with (R3)3N, to provide the cationic surfactant. 13. The method of claim 11, further comprising: reacting HOC(O)-R1 with a compound having the structure to provide a terminal amine having the structure acidifying the terminal amine to provide an ammonium salt; treating the ammonium salt with an epihalohydrin to provide a gamma hydroxy haloammonium salt; and treating the gamma hydroxy haloammonium salt with (R3)3N having the structure , to provide the cationic surfactant. 14. The method of claim 11, further comprising: acidifying an amine having the structure wherein R4 is chosen from a substituted or unsubstituted (C4-C22)alkyl and a substituted or unsubstituted (C4-C22)alkenyl, wherein R4 is optionally modified, the modification comprising maleic anhydride modification, polymerization, ene-reaction modified, hydrogenation, isomerization, branching, or a combination thereof. to provide an ammonium salt; treating the ammonium salt with an epihalohydrin to provide a gamma hydroxy haloammonium salt; and treating the gamma hydroxy haloammonium salt with (R3)3N, to provide the cationic surfactant. 15. The method of any of Claims 9-14, wherein the method further includes treating the cationic latex emulsion with an acid to reduce the viscosity of the cationic latex emulsion. 16. The method of Claim 13 wherein R3 is chosen from substituted or unsubstituted linear or branched (C1-C6)alkyl, substituted or unsubstituted linear or branched (C1-C6)alkenyl, and substituted or unsubstituted (C1-C6)alkyl alcohol. 17. An asphalt emulsion comprising the cationic latex emulsion of claim 1. 18. The asphalt emulsion of claim 17, wherein the asphalt emulsion comprises bitumen, an aqueous liquid, and the cationic latex emulsion of claim 1. 19. An asphalt emulsion comprising: the cationic latex emulsion of claim 1; and cationic bitumen particles. 20. A method of forming the asphalt emulsion of claim 17, the method comprising: combining a cationic asphalt emulsion with the cationic latex emulsion, to form the asphalt emulsion of claim 17. 21. A method of coating a carpet to form a carpet back coating, the method comprising: coating the carpet with the cationic latex emulsion of claim 1 to form the carpet back coating thereon. 22. A paper coating, tires, asphalt concrete, carpet back coating, latex paint, foam, or ink comprising: the cationic latex emulsion of claim 1. |
Scheme 2. Example 5. Hydroxy propyl di-quaternary ammonium compound of coconut fatty acid and DMAPA amidoamine made with Methyldiethanolamine (MDEA) in ethanol. [000102] Coconut Fatty acids can be used as a desirable and unique source of fatty acids. 343.66 g (1 mol) of Coconut Fatty acids and 185.88 g of dimethylaminopropylamine (DMAPA) (1.10 mol) were added to a 1000 mL round bottom flask under distillation system. The mixture was heated to 120 °C for 30 minutes to allow the salt intermediates to melt. Reaction was then continued at 160-170 ºC to undergo amidation under a nitrogen gas sparge (150-300 L/hr). Both the TAV and AV were closely monitored throughout the reaction. The reaction was deemed complete once the AV levels were within 0-10 mg KOH/g, indicating a desired level of fatty acid containing material consumption. The amidoamine adduct had a TAV of 190.13 mg KOH/g and an AV of 7.11 mg KOH/g. Upon completion of amidoamine adduct (1.00 mol), 158.73 g of ethanol and 43.18 g of deionized water were charged in a 1000 mL round bottom flask, mixed, and refluxed for 10 minutes under nitrogen blanket followed by dropwise addition of 66.18g of 31-37% hydrochloric acid solution (0.98 mol) in the reaction with an addition funnel. The mixture was heated to 60 ºC under reflux for 3-5 hours to form an amine hydrochloride salt. The reaction was monitored by AHV and TAV until the TAV was within 0- 5 mg KOH/g. Amine hydrochloride salts had an AHV of 80.59 mg KOH/g and a TAV of 3.79 mg KOH/g. After 3-5 hours of reaction, 61.37g of epichlorohydrin (0.97 mol) was added drop- wise to the reaction and was continued at 80 ºC for 5-7 hours to form the alkyl chloride intermediate, wherein the R-amido group corresponds to the fatty acid converted to an amide. Reaction was monitored by AHV and chloride titration. The intermediate had an AHV of 3.81 mg KOH/g and a chloride concentration of 3.33%. Reaction temperature was cooled down to 50-60 ºC prior to Trimethylamine addition. 76.90 g of Methyldiethanolamine (0.95 mol) was added dropwise into the reaction and was continued stirring for 3-5 hours at 70-80 ºC. Reaction was monitored by chloride titration and TAV. The final diquat product had a chloride concentration of 6.82%. [000103] Scheme 3 illustrates the reactions performed in Examples 6, 7, and 8, forming the tertiary amine-based surfactant or surfactant composition with varying degrees of fatty tail length pertaining the dodecyl-, hexadecyl-, and octadecyl- fatty tail of the surfactant. Scheme 3. Example 6. N 1 -dodecyl-2-hydroxy-N 1 ,N 1 ,N 3 ,N 3 ,N 3 -pentamethylpropane-1,3-diaminium chloride (1:2) in diethylene glycol [000104] 43.10 g of dimethylaurylamine (N,N-dimethyldodecylamine, 1.00 mol) was charged in a 500 mL flask. 40.00 g of diethylene glycol and 10.00 g of deionized water were charged in a 500 mL round bottom flask, mixed, and refluxed for 10 minutes under nitrogen blanket followed by dropwise addition of 19.46 g of 31-37% hydrochloric acid solution (0.98 mol) in the reaction with an addition funnel. Diethylene glycol was selected to keep the liquidity of the salts adduct. The mixture was heated to 60 ºC under reflux for 3-5 hours to form an amine hydrochloride salts. The reaction was monitored by AHV and TAV until the TAV was within 0-5 mg KOH/g. Amine hydrochloride salts had an AHV of 101.02 mg KOH/g and a TAV of 1.35 mg KOH/g. After 3-5 hours of reaction, 17.55 g of epichlorohydrin (0.97 mol) was added drop-wise to the reaction and was continued at 80 ºC for 5-7 hours to form N-(3- chloro-2-hydroxypropyl)-N,N-dimethyldodecan-1-aminium chloride (1:1) intermediate. Reaction was monitored by AHV and chloride titration. The intermediate had an AHV of 4.26 mg KOH/g and a chloride concentration of 5.17%. Reaction temperature was cooled down to 50-60 ºC prior to trimethylamine addition.21.25 g of trimethylamine, 50% solution in water (0.90 mol) was added dropwise into the reaction and was continued stirring for 3-5 hours at 70- 80 ºC. Reaction was monitored by chloride titration and TAV. The final product, N 1 -dodecyl-2- hydroxy-N 1 ,N 1 ,N 3 ,N 3 ,N 3 -pentamethylpropane-1,3-diaminium chloride (1:2), had an TAV of 3.22 mg KOH/g and a chloride concentration of 7.65%. Example 7. N 1 -hexadecyl-2-hydroxy-N 1 ,N 1 ,N 3 ,N 3 ,N 3 -pentamethylpropane-1,3-diaminium chloride (1:2) in diethylene glycol. [000105] 43.10 g of N,N-dimethylhexadecylamine (1.00 mol) was charged in a 500 mL flask.55.08 g of diethylene glycol and 25.00 g of deionized water were charged in a 500 mL round bottom flask, mixed, and refluxed for 10 minutes under nitrogen blanket followed by dropwise addition of 15.44 g of 31-37% hydrochloric acid solution (0.98 mol) in the reaction with an addition funnel. Diethylene glycol was selected to keep the liquidity of the salts adduct. The mixture was heated to 60 ºC under reflux for 3-5 hours to form an amine hydrochloride salts. The reaction was monitored by AHV and TAV until the TAV was within 0-5 mg KOH/g. Amine hydrochloride salts had an AHV of 68.27 mg KOH/g and a TAV of 2.79 mg KOH/g. After 3-5 hours of reaction, 14.06 g of epichlorohydrin (0.97 mol) was added drop-wise to the reaction and was continued at 80 ºC for 5-7 hours to form N-(3-chloro-2-hydroxypropyl)-N,N- dimethylhexadecan-1-aminium chloride (1:1) intermediate. Reaction was monitored by AHV and chloride titration. The intermediate had an AHV of 3.68 mg KOH/g and a chloride concentration of 3.60%. Reaction temperature was cooled down to 50-60 ºC prior to trimethylamine addition. 16.88 g of trimethylamine, 50% solution in water (0.95 mol) was added dropwise into the reaction and was continued stirring for 3-5 hours at 70-80 ºC. Reaction was monitored by chloride titration and TAV. The final product, N 1 -hexadecyl-2-hydroxy- N 1 ,N 1 ,N 3 ,N 3 ,N 3 -pentamethylpropane-1,3-diaminium chloride (1:2), had a TAV of 0.95 mg KOH/g and a chloride concentration of 6.40%. Example 8. 1,3-Propanediaminium, 2-hydroxy-N 1 ,N 1 ,N 1 ,N 3 ,N 3 -pentamethyl-N 3 -octadecyl-, chloride (1:2) in diethylene glycol [000106] 65.00 g of N,N-octadecyldimethylamine (1.00 mol) was charged in a 500 mL flask.79.21 g of diethylene glycol and 20.00 g of deionized water were charged in a 500 mL round bottom flask, mixed, and refluxed for 10 minutes under nitrogen blanket followed by dropwise addition of 21.09 g of 31-37% hydrochloric acid solution (0.98 mol) in the reaction with an addition funnel. Diethylene glycol was selected to keep the liquidity of the salts adduct. The mixture was heated to 60 ºC under reflux for 3-5 hours to form an amine hydrochloride salts. The reaction was monitored by AHV and TAV until the TAV was within 0-5 mg KOH/g. Amine hydrochloride salts had an AHV of 65.81 mg KOH/g and a TAV of 2.11 mg KOH/g. After 3-5 hours of reaction, 16.33 g of epichlorohydrin (0.96 mol) was added drop-wise to the reaction and was continued at 80 ºC for 5-7 hours to form N-(3-chloro-2-hydroxypropyl)-N,N- dimethylhexadecan-1-aminium chloride (1:1) intermediate. Reaction was monitored by AHV and chloride titration. The intermediate had an AHV of 1.82 mg KOH/g and a chloride concentration of 3.21%. Reaction temperature was cooled down to 50-60 ºC prior to trimethylamine addition.23.49 g of trimethylamine, 50% solution in water (0.95 mol) was added dropwise into the reaction and was continued stirring for 3-5 hours at 70-80 ºC. Reaction was monitored by chloride titration and TAV. The final product, N 1 -octadecyl-2-hydroxy- N 1 ,N 1 ,N 3 ,N 3 ,N 3 -pentamethylpropane-1,3-diaminium chloride (1:2), had a TAV of 1.12 mg KOH/g and a chloride concentration of 6.95%. Example 9. N 1 -dodecyl-2-hydroxy-N 1 ,N 1 ,N 3 ,N 3 ,N 3 -pentamethylpropane-1,3-diaminium chloride (1:2) in ethanol [000107] 80.00 g of dimethylaurylamine (N,N-dimethyldodecylamine, 1.00 mol) was charged in a 500 mL flask. 70.00 g of ethanol and 15.00 g of deionized water were charged in a 500 mL round bottom flask, mixed, and refluxed for 10 minutes under nitrogen blanket followed by dropwise addition of 36.12 g of 31-37% hydrochloric acid solution (0.98 mol) in the reaction with an addition funnel. The mixture was heated to 60 ºC under reflux for 3-5 hours to form an amine hydrochloride salts. The reaction was monitored by AHV and TAV until the TAV was within 0-5 mg KOH/g. Amine hydrochloride salts had an AHV of 117.10 mg KOH/g and a TAV of 1.57 mg KOH/g. After 3-5 hours of reaction, 32.63 g of epichlorohydrin (0.97 mol) was added drop-wise to the reaction and was continued at 80 ºC for 5-7 hours to form N-(3- chloro-2-hydroxypropyl)-N,N-dimethyldodecan-1-aminium chloride (1:1) intermediate. Reaction was monitored by AHV and chloride titration. The intermediate had an AHV of 3.53mg KOH/g and a chloride concentration of 5.02%. Reaction temperature was cooled down to 50-60 ºC prior to trimethylamine addition.36.21g of trimethylamine, 50% solution in water (0.90 mol) was added dropwise into the reaction and was continued stirring for 3-5 hours at 70- 80 ºC. Reaction was monitored by chloride titration and TAV. The final product, N 1 -dodecyl-2- hydroxy-N 1 ,N 1 ,N 3 ,N 3 ,N 3 -pentamethylpropane-1,3-diaminium chloride (1:2), had an TAV of 3.51 mg KOH/g and a chloride concentration of 7.85%. [000108] Scheme 4 illustrates the reactions performed in Example 10, forming the tertiary amine-based surfactant or surfactant composition with a quaternary ammonium cation consisting of two alkyl ethanol polar functionality groups and one methyl group.
Scheme 4. Example 10. 1,3-Propanediaminium, 2-hydroxy-N 1 ,N 1 -bis(2-hydroxyethyl)-N 1 ,N 3 ,N 3 -trimethyl- N 3 -dodecyl-, chloride in ethanol. [000109] 48.07 g of dimethylaurylamine (N,N-dimethyldodecylamine, 1.00 mol) was charged in a 500 mL flask.40.10 g of ethanol and 10.48 g of deionized water were charged in a 500 mL round bottom flask, mixed, and refluxed for 10 minutes under nitrogen blanket followed by dropwise addition of 21.70 g of 31-37% hydrochloric acid solution (0.98 mol) in the reaction with an addition funnel. The mixture was heated to 60 ºC under reflux for 3-5 hours to form an amine hydrochloride salts. The reaction was monitored by AHV and TAV until the TAV was within 0-5 mg KOH/g. Amine hydrochloride salts had an AHV of 113.10 mg KOH/g and a TAV of 1.72 mg KOH/g. After 3-5 hours of reaction, 20.05g of epichlorohydrin (0.97 mol) was added drop-wise to the reaction and was continued at 80 ºC for 5-7 hours to form N-(3-chloro-2- hydroxypropyl)-N,N-dimethyldodecan-1-aminium chloride (1:1) intermediate. Reaction was monitored by AHV and chloride titration. The intermediate had an AHV of 4.26 mg KOH/g and a chloride concentration of 5.09%.22.39 g of methyldiethanolamine (MDEA) was added dropwise into the reaction and was continued stirring for 3-5 hours at 70-80 ºC. Reaction was monitored by chloride titration and TAV. The final product, 1,3-Propanediaminium, 2-hydroxy- N 1 ,N 1 -bis(2-hydroxyethyl)-N 1 ,N 3 ,N 3 -trimethyl-N 3 -dodecyl-, chloride (1:2) had an TAV of 5.29 mg KOH/g and a chloride concentration of 6.21%. Example 11. 1,3-Propanediaminium, N 1 -dodecyl-2-hydroxy-N 3 -(2-hydroxyethyl)-N 1 ,N 1 ,N 3 ,N 3 - tetramethyl-, chloride (1:2) [000110] 48.07 g of dimethylaurylamine (N,N-dimethyldodecylamine, 1.00 mol) was charged in a 500 mL flask.30.10 g of ethanol and 10.48 g of deionized water were charged in a 500 mL round bottom flask, mixed, and refluxed for 10 minutes under nitrogen blanket followed by dropwise addition of 21.70 g of 31-37% hydrochloric acid solution (0.98 mol) in the reaction with an addition funnel. The mixture was heated to 60 ºC under reflux for 3-5 hours to form an amine hydrochloride salts. The reaction was monitored by AHV and TAV until the TAV was within 0-5 mg KOH/g. Amine hydrochloride salts had an AHV of 113.10 mg KOH/g and a TAV of 1.72 mg KOH/g. After 3-5 hours of reaction, 20.05g of epichlorohydrin (0.97 mol) was added drop-wise to the reaction and was continued at 80 ºC for 5-7 hours to form N-(3-chloro-2- hydroxypropyl)-N,N-dimethyldodecan-1-aminium chloride (1:1) intermediate. Reaction was monitored by AHV and chloride titration. The intermediate had an AHV of 4.26 mg KOH/g and a chloride concentration of 5.09%.18.21 g of dimethylethanolamine (DMEA) was added dropwise into the reaction and was continued stirring for 3-5 hours at 70-80 ºC. Reaction was monitored by chloride titration and TAV. The final product, 1,3-Propanediaminium, N 1 - dodecyl-2-hydroxy-N 3 -(2-hydroxyethyl)-N 1 ,N 1 ,N 3 ,N 3 -tetramethyl-, chloride (1:2) had an TAV of 3.22 mg KOH/g and a chloride concentration of 6.21%. [000111] Following the below procedures, a cationic latex emulsions (e.g. Examples 12- 29) were prepared by incorporating different iterations of cationic surfactant (Examples 1-11) into an anionic latex at different levels of surfactant dosage (BWS = by weight of surfactant; BWALS = by weight of anionic latex solids; BWE = by weight of total emulsion). Table 4 illustrates the composition of cationic latex. Some of the described examples 12, 13, 14, 15, and 29 of the cationic latex was further treated with 37% hydrochloric acid solution (37% HCl aq.) down to a pH of 5.30 or in some cases 3.00 (e.g. cationic latex example 29) to further decrease the viscosity of the final cationic latex. It is understood that other organic acids can be used to further lower the pH of the cationic latex emulsions. Table 4. Generic formula of Cationic latex. Example 12. Preparation of Cationic latex with hydroxy propyl di-quaternary ammonium compound of coconut fatty acid and DMAPA amidoamine made with Trimethylamine in ethanol [000112] 150.0 g of the high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% was prepared and agitated at 100-500 rpm with a low shear overhead mixer to achieve a homogenous solution at 25 º C. A blend of cationic surfactant solution of Example 1 at 4.50% BWALS and DI water were added to the anionic latex slowly with continued agitation for 1 minute. Final cationic latex had a viscosity of 261.00 cP at 25 º C after the solution was sufficiently agitated at 500-1000 rpm for 1 minute. The addition of the 37% HCl solution to a pH of 5.30 did not have any impact on the viscosity of the final mix. Example 13. Preparation of Cationic latex with a blend of 80% hydroxy propyl di-quaternary ammonium compound of coconut fatty acid and DMAPA amidoamine made with Trimethylamine (TMA) in ethanol and 20% hydroxy propyl di-quaternary ammonium compound of distillate fatty acids and DMAPA amidoamine in ethanol. [000113] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above in Example 12 with the exception that a blend of cationic surfactant solution of Example 1, Example 2, and water were added to the anionic latex slowly with continued agitation for 1 minute. Significant viscosity build-up was seen in relation to the cationic surfactant blend charge. The solution was sufficiently agitated at 500-1000 rpm until the viscosity reached 690.00 cP at 25 º C. pH of the cationic latex was adjusted down to 5.30 by adding 37% hydrochloric acid solution bringing down the pH to 5.30 and viscosity of 285.83 cP. Example 14. Preparation of Cationic latex with a blend of 50% hydroxy propyl di-quaternary ammonium compound of coconut fatty acid and DMAPA amidoamine made with Trimethylamine (TMA) in ethanol and 50% hydroxy propyl di-quaternary ammonium compound of distillate fatty acids and DMAPA amidoamine in ethanol. [000114] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above in Example 13. Final cationic latex had a viscosity of 22,830.00 cP at 25 º C. pH of the cationic latex was adjusted down to 5.30 by adding 37% hydrochloric acid solution bringing down the pH to 5.30 and viscosity of 679.76 cP. Example 15. Preparation of Cationic latex with hydroxy propyl di-quaternary ammonium compound of distillate fatty acids and DMAPA amidoamine in ethanol. [000115] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above with the exception that a blend of cationic surfactant solution of Example 2 at 5.20% BWALS and water was used in the formulation. Final cationic latex had a viscosity of 274,600 cP at 25 º C. pH of the cationic latex was adjusted down to 5.30 by adding 37% hydrochloric acid solution bringing down the pH to 5.30 and viscosity of 1,092 cP. Example 16. Preparation of Cationic latex with a blend of 70% hydroxy propyl di-quaternary ammonium compound of coconut fatty acid and DMAPA amidoamine made with Trimethylamine (TMA) and 30% hydroxy propyl di-quaternary ammonium compound of coconut [000116] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above with the exception that a blend of cationic surfactant solution of Example 1, Example 5, and water were added to the anionic latex slowly with continued agitation for 1 minute. Small degree of viscosity build-up was seen in relation to the cationic surfactant blend charge. The solution was sufficiently agitated at 500-1000 rpm until the viscosity reached 352.00 cP at 25 º C. Example 17. Preparation of Cationic latex with a blend of 30% hydroxy propyl di-quaternary ammonium compound of coconut fatty acid and DMAPA amidoamine made with Trimethylamine (TMA) and 70% hydroxy propyl di-quaternary ammonium compound of coconut. [000117] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above. Final cationic latex had a viscosity of 1,429.00 cP at 25 º C. Example 18. Preparation of Cationic latex with hydroxy propyl di-quaternary ammonium compound of coconut fatty acid and DMAPA amidoamine made with Methyldiethanolamine (MDEA). [000118] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above in Example 12 with the exception that a blend of cationic surfactant solution of Example 5 at 4.50% BWALS and water was used. Final cationic latex had a viscosity of 24,080 cP at 25 º C. Example 19. Preparation of Cationic latex with N 1 -dodecyl-2-hydroxy- N 1 ,N 1 ,N 3 ,N 3 ,N 3 - pentamethylpropane-1,3-diaminium chloride (1:2) [000119] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above with the exception that Example 6 was added to the anionic latex. Final cationic latex had a viscosity of 4,340.00 cP at 25 º C. Example 20. Preparation of Cationic latex with N 1 -hexadecyl-2-hydroxy-N 1 ,N 1 ,N 3 ,N 3 ,N 3 - pentamethylpropane-1,3-diaminium chloride (1:2). [000120] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above with the exception that Example 7 was added to the anionic latex. Final cationic latex had a viscosity of 6,123.00 cP at 25 º C. Example 21. Preparation of Cationic latex with 1,3-Propanediaminium, 2-hydroxy-N 1 ,N 1 ,N 1 ,N 3 , N 3 -pentamethyl-N 3 -octadecyl-, chloride (1:2). [000121] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above in Example 12 with the exception that Example 8 was added to the anionic latex. Significant viscosity build-up was seen in relation to the cationic surfactant blend charge. Final cationic latex had a viscosity of 94,240 cP at 25 º C. Example 22. Preparation of Cationic latex with N 1 -dodecyl-2-hydroxy-N 1 ,N 1 ,N 3 ,N 3 ,N 3 - pentamethylpropane-1,3-diaminium chloride (1:2). [000122] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above with the exception that Example 9 was added to the anionic latex. Final cationic latex had a viscosity of 454.00 cP at 25 º C. Example 23. Preparation of Cationic latex with 1,3-Propanediaminium, 2-hydroxy-N 1 ,N 1 -bis(2- hydroxyethyl)-N 1 ,N 3 ,N 3 -trimethyl-N 3 -dodecyl-, chloride (1:2). [000123] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above with the exception that Example 10 was added to the anionic latex. Final cationic latex had a viscosity of 13,520.00 cP at 25 º C. Example 24. Preparation of Cationic latex with Hydroxy propyl di-quaternary ammonium compound of hydrogenated distillate stearic fatty acids and DMAPA amidoamine made with Trimethylamine (TMA). [000124] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above with the exception that Example 3 was added to the anionic latex. Significant viscosity build-up was seen in relation to the cationic surfactant blend charge. Final cationic latex had a viscosity of >500,000 cP at 25 º C. Example 25. Preparation of Cationic latex with 1,3-Propanediaminium, N 1 -dodecyl-2-hydroxy- N 3 -(2-hydroxyethyl)-N 1 ,N 1 ,N 3 ,N 3 -tetramethyl-, chloride (1:2) [000125] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above in Example 12 with the exception that Example 11 was added to the anionic latex. Example 26. Preparation of Cationic latex with a blend of 60% N 1 -dodecyl-2-hydroxy- N 1 ,N 1 ,N 3 ,N 3 ,N 3 -pentamethylpropane-1,3-diaminium chloride (1:2) and 40% 1,3- Propanediaminium, 2-hydroxy-N 1 ,N 1 -bis(2-hydroxyethyl)-N 1 ,N 3 ,N 3 -trimethyl-N 3 -dodecyl-, chloride (1:2). [000126] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above. with the exception that a blend of Example 9 and Example 10 was added to the anionic latex. Final cationic latex had a viscosity of 926.00 cP at 25 º C. Example 27. Preparation of Cationic latex with a blend of 40% N 1 -dodecyl-2-hydroxy- N 1 ,N 1 ,N 3 ,N 3 ,N 3 -pentamethylpropane-1,3-diaminium chloride (1:2) and 60% 1,3- Propanediaminium, 2-hydroxy-N 1 ,N 1 -bis(2-hydroxyethyl)-N 1 ,N 3 ,N 3 -trimethyl-N 3 -dodecyl-, chloride (1:2). [000127] Cationic latex was prepared with a high molecular weight styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described above. Final cationic latex had a viscosity of 1222.00 cP at 25 º C. Example 28. Preparation of Cationic latex with a retail store available liquid rubber product: Ames’ Liquid Rubber Waterproof Sealer. [000128] 115g of carboxylated styrene-butadiene rubber with a residue content of 55-70% was prepared and agitated at 100-500 rpm with a low shear overhead mixer to achieve a homogenous solution at 25 º C. A blend of 5.5g cationic surfactant solution of Example 1 and 4.75 g of water were added to the anionic latex slowly with continued agitation for 1 minute. Example 29. Preparation of Cationic latex with Hydroxy propyl di-quaternary ammonium compound of coconut fatty acid and DMAPA amidoamine made with Methyldiethanolamine (MDEA). [000129] Cationic latex was prepared from a crosslinked styrene-butadiene copolymer anionic latex with a residue content of 70% following the same procedure as described in 12 with the exception that Example 5 at 4.25% BWALS was added to the anionic latex.37% HCl solution was added to the latex subsequently to the latex mix. Viscosity was monitored throughout the addition of the HCl soln. at different pH levels from 9.00 to 3.00. Final cationic latex had a viscosity of 455.00 cP at 25 º C and a pH of 3.00. [000130] Different variations of amidoamine and/or tertiary amine-based cationic surfactant using various starting materials can be synthesized, co-blended, and formulated to achieve a desired range of viscosity of the cationic latex by tuning the hydrophilic and hydrophobic profile of the surfactant. [000131] Viscosity of the cationic latex can be adjusted by modification of average fatty chain length per molecule of the both amidoamine and tertiary amine-based cationic latices. [000132] Increase in viscosity of the cationic latex examples 12-15 containing different levels of surfactant example 1 and example 2 by weight ratio, % BWS is seen depending on the type of fatty acid used for preparation of the amidoamine-based cationic surfactant. Table 5 and Graph 1 illustrate the impact of the average fatty chain length of the surfactant on the viscosity of the cationic latex potentially changing the distribution of the cationic latex. It can be noted that the viscosity of the cationic latex is observed with the increase in the ratio of surfactant Example 2 in the cationic latex mix, coupled with the increase in average molecular weight of the surfactant compound. (e.g. Example 12 which is a cationic styrene butadiene latex composed of surfactant example 1 or amidoamine-based cationic surfactant with coconut fatty acid chain had the least viscosity reading compared to the Example 15 latex which is composed of example 2 or cationic surfactant with soy fatty acid chain.)
Table 5. Cationic latex emulsion examples 12-15 prepared using amidoamine-based cationic surfactants with varying average fatty chain length at minimum surfactant dosage required to convert from anionic latex to cationic latex emulsion. It is understood that the synthesis of the different types of cationic surfactants made with various starting materials and the blending of the final product of different types of cationic surfactants are being used interchangeably in the Examples. [000133] Notable viscosity change in cationic latex was also observed with varying length of fatty chain of the tertiary amine based cationic surfactant. (e.g. Examples 19-21, viscosity of the cationic latex is increased from 4,340 cP to 94,240 cP choosing from dodecyl or C 12 H 25 - to octadecyl or C18H37- fatty tail of the tertiary amine-based surfactant.) Table 6. Cationic latex emulsions prepared using tertiary amine based cationic surfactants.
[000134] Viscosity of the cationic latex can be further adjusted down by adding 31-37% of HCl acid solution to the surfactant incorporated cationic latex. Significant drop in viscosity of the cationic latex emulsion can be seen by further adding 37% HCl acid soln. into the surfactant treated-cationic latices going from pH of 9.00 to 3.00. [000135] Relationship between the type of fatty acids used for the preparation of amidoamine-based cationic surfactant and the viscosity of the pH-adjusted styrene-butadiene copolymer cationic latex examples 12-15 containing different levels of cationic surfactant of example 1 and 2 is observed in Graph 2 and Table 5. [000136] Viscosity of the latex emulsion can be further adjusted by adding 37% HCl acid soln. into the surfactant treated cationic latex to a pH of 3.00. Table 7 and Graph 3 illustrate the relationship between the pH and the viscosity of the cross-linked cationic latex example 29. Table 7. Decrease in viscosity of cationic latex example 29 in relation to the pH drop of latex
[000137] Increase in viscosity of the cationic latices was also seen depending on the inclusion of polar functionalities of the amine material used for synthesis of the amidoamine- based cationic surfactant. Viscosity of the cationic latex can be adjusted by modification of polar functionalities per molecule of the cationic surfactant as shown in cationic latex examples 12, 16, 17, and 18 containing different levels of surfactant example 1 and example 5. Table 8 and Graph 4 illustrate the impact of varying polar functionalities per molecule of the cationic surfactant on the viscosity of the cationic latex. Table 8. Cationic latex emulsions prepared using amidoamine-based cationic surfactants with varying hydroxyl functional groups on the terminal quat at a fixed pH of 9.00-10.00. [000138] The terms and expressions that have been employed are used as terms of description and not of limitation, and there is no intention in the use of such terms and expressions of excluding any equivalents of the features shown and described or portions thereof, but it is recognized that various modifications are possible within the scope of the embodiments of the present invention. Thus, it should be understood that although the present invention has been specifically disclosed by specific embodiments and optional features, modification and variation of the concepts herein disclosed may be resorted to by those of ordinary skill in the art, and that such modifications and variations are considered to be within the scope of embodiments of the present invention. Exemplary Embodiments. [000139] The following exemplary embodiments are provided, the numbering of which is not to be construed as designating levels of importance: [000140] Embodiment 1 provides a cationic latex emulsion comprising: latex particles; an aqueous liquid emulsified with the latex particles; and a cationic surfactant having the structure: , wherein at each occurrence R 2 is independently chosen from substituted or unsubstituted linear or branched (C 1 -C 6 )alkyl, substituted or unsubstituted linear or branched (C 1 -C 6 )alkenyl, substituted or unsubstituted (C 4 -C 10 )cycloalkyl or (C 4 -C 10 )cycloalkenyl, substituted or unsubstituted (C 1 -C 10 )alkoxy (for example, substituted or unsubstituted (C 1 -C 6 ) alkoxy), including but not limited to (C 1 -C 10 )alkyl alcohol, (C 1 -C 10 )alkyl ether or (C 1 -C 10 )alkoxyalcohol, and substituted or unsubstituted (C 4 -C 10 )aryl, or wherein R 2 together with another R 2 forms a substituted or unsubstituted aliphatic or aromatic (C 4 -C 12 )heterocycle together with the nitrogen to which they are attached; at each occurrence R 3 is independently chosen from substituted or unsubstituted linear or branched (C 1 -C 6 )alkyl, substituted or unsubstituted linear or branched (C 1 -C 6 )alkenyl, substituted or unsubstituted (C 4 -C 10 )cycloalkyl or (C 4 -C 10 )cycloalkenyl, substituted or unsubstituted (C 1 -C 10 )alkoxy (for example, substituted or unsubstituted (C 1 -C 6 ) alkoxy),including but not limited to (C 1 -C 10 )alkyl alcohol, (C 1 -C 10 )alkyl ether or (C 1 - C 10 )alkoxyalcohol and substituted or unsubstituted (C 4 -C 10 )aryl, or wherein R 3 together with another R 3 forms a substituted or unsubstituted aliphatic or aromatic (C 4 -C 12 )heterocycle together with the nitrogen to which they are attached; at each occurrence X- is independently chosen from an anion; R A is chosen from a substituted or unsubstituted (C 4 -C 22 )alkyl, a substituted or unsubstituted (C 4 -C 22 )alkenyl, and R 1 is chosen from a substituted or unsubstituted (C 4 -C 22 )alkyl and a substituted or unsubstituted (C 4 -C 22 )alkenyl, wherein R 1 is optionally modified, the modification comprising maleic anhydride modification, polymerization, ene-reaction modified, hydrogenation, isomerization, branching, or a combination thereof; A is -NH- or -O-; E is -CH 2 -, -((C 2 -C 4 )alkoxy) n3 -, or -O-; n1 is an integer that is 0 to 9; n2 is an integer that is 0 to 9; n1 + n2 is 1 to 10; and n3 is an integer that is 1 to 40. [000141] Embodiment 2 provides the cationic latex emulsion of Embodiment 1, wherein E is -CH 2 -. [000142] Embodiment 3 provides the cationic latex emulsion of any one of Embodiments 1-2, wherein at each occurrence R 2 is independently chosen from substituted or unsubstituted (C 1 -C 6 )alkyl and substituted or unsubstituted (C 1 -C 6 )alkyl alcohol. [000143] Embodiment 4 provides the cationic latex emulsion of any one of Embodiments 1-3, wherein at each occurrence R 3 is independently chosen from substituted or unsubstituted (C 1 -C 6 )alkyl and substituted or unsubstituted (C 1 -C 6 )alkyl alcohol. [000144] Embodiment 5 provides the cationic latex emulsion of any one of Embodiments 1-4, wherein R A is chosen from a substituted or unsubstituted (C 4 -C 22 )alkyl, a substituted or unsubstituted (C 4 -C 22 )alkenyl, and . [000145] Embodiment 6 provides the cationic latex emulsion of any one of Embodiments 1-5, wherein: at each occurrence R 2 is independently chosen from substituted or unsubstituted (C 1 - C6)alkyl; at each occurrence R 3 is independently chosen from substituted or unsubstituted (C 1 - C6)alkyl; at each occurrence X- is independently chosen from an anion; R A is chosen from a substituted or unsubstituted (C 4 -C 22 )alkyl, a substituted or unsubstituted (C 4 -C 22 )alkenyl, and ; R 1 is chosen from a substituted or unsubstituted (C 4 -C 22 )alkyl and a substituted or unsubstituted (C 4 -C 22 )alkenyl, wherein R 1 is optionally modified, the modification comprising maleic anhydride modification, polymerization, ene-reaction modified, hydrogenation, isomerization, branching, or a combination thereof; A is -NH- or -O-; and n is 1 to 10. [000146] Embodiment 7 provides the cationic latex emulsion of any one of Embodiments 1-6, wherein at each occurrence R 2 is independently chosen from methyl and ethyl. [000147] Embodiment 8 provides the cationic latex emulsion of any one of Embodiments 1-7, wherein at each occurrence R 2 is methyl. [000148] Embodiment 9 provides the cationic latex emulsion of any one of Embodiments 1-8, wherein at each occurrence R 3 is independently chosen from methyl and ethyl. [000149] Embodiment 10 provides the cationic latex emulsion of any one of Embodiments 1-9, wherein R 3 is methyl. [000150] Embodiment 11 provides the cationic latex emulsion of any one of Embodiments 1-10, wherein X- is an organic anion. [000151] Embodiment 12 provides the cationic latex emulsion of any one of Embodiments 1-11, wherein X- is an inorganic anion. [000152] Embodiment 13 provides the cationic latex emulsion of any one of Embodiments 1-12, wherein at each occurrence X- is independently chosen from a (C 1 -C 10 )carboxylic acid conjugate base, sulfate, Cl-, Br-, I-, and NO3-. [000153] Embodiment 14 provides the cationic latex emulsion of any one of Embodiments 1-13, wherein R A is independently chosen from a substituted or unsubstituted (C 4 -C 22 )alkyl and a substituted or unsubstituted (C 4 -C 22 )alkenyl. [000154] Embodiment 15 provides the cationic latex emulsion of Embodiment 14, wherein R A is (C 10 -C 20 )alkyl. [000155] Embodiment 16 provides the cationic latex emulsion of any one of Embodiments 1-15, wherein R A is . [000156] Embodiment 17 provides the cationic latex emulsion of Embodiment 16, wherein R A is . [000157] Embodiment 18 provides the cationic latex emulsion of any one of Embodiments 1-17, wherein R 1 is (C 10 -C 20 )alkyl. [000158] Embodiment 19 provides the cationic latex emulsion of any one of Embodiments 1-18, wherein R 1 is (C 10 -C 14 )alkyl. [000159] Embodiment 20 provides the cationic latex emulsion of any one of Embodiments 1-19, wherein R 1 is C 12 alkyl. [000160] Embodiment 21 provides the cationic latex emulsion of any one of Embodiments 1-20, wherein R 1 is derived from a bio-based fatty acid source. [000161] Embodiment 22 provides the cationic latex emulsion of any one of Embodiments 1-21, wherein R 1 is derived from a petrochemical fatty acid source. [000162] Embodiment 23 provides the cationic latex emulsion of any one of Embodiments 1-22, wherein R 1 is unmodified. [000163] Embodiment 24 provides the cationic latex emulsion of any one of Embodiments 1-23, wherein R 1 is modified, the modification comprising maleic anhydride modification, ene- reaction modified, hydrogenation, isomerization, polymerization, branching, or a combination thereof. [000164] Embodiment 25 provides the cationic latex emulsion of any one of Embodiments 1-24, wherein A is -NH-. [000165] Embodiment 26 provides the cationic latex emulsion of any one of Embodiments 1-25, wherein A is -O-. [000166] Embodiment 27 provides the cationic latex emulsion of any one of Embodiments 1-26, wherein n1 + n2 is 1 to 6. [000167] Embodiment 28 provides the cationic latex emulsion of any one of Embodiments 1-27, wherein n1 + n2 is 1 to 3. [000168] Embodiment 29 provides the cationic latex emulsion of any one of Embodiments 1-28, wherein n1 + n2 is 1. [000169] Embodiment 30 provides the cationic latex emulsion of any one of Embodiments 1-29, wherein n is 1 to 6. [000170] Embodiment 31 provides the cationic latex emulsion of any one of Embodiments 1-30, wherein n is 1 to 3. [000171] Embodiment 32 provides the cationic latex emulsion of any one of Embodiments 1-31, wherein n is 1. [000172] Embodiment 33 provides the cationic latex emulsion of any one of Embodiments 1-32, wherein the cationic surfactant has the structure: . [000173] Embodiment 34 provides the cationic latex emulsion of any one of Embodiments 1-33, wherein the cationic surfactant has the structure: wherein R 4 is chosen from a substituted or unsubstituted (C 4 -C 22 )alkyl and a substituted or unsubstituted (C 4 -C 22 )alkenyl, wherein R 4 is optionally modified, the modification comprising maleic anhydride modification, polymerization, ene-reaction modified, hydrogenation, isomerization, branching, or a combination thereof. [000174] Embodiment 35 provides the cationic latex emulsion of any one of Embodiments 1-34, wherein the cationic latex emulsion comprises 0.1% to 20% of the cationic surfactant by weight of the latex particles. [000175] Embodiment 36 provides the cationic latex emulsion of any one of Embodiments 1-35, wherein the cationic latex emulsion comprises 0.5% to 10% of the cationic surfactant by weight of the latex particles. [000176] Embodiment 37 provides the cationic latex emulsion of any one of Embodiments 1-36, wherein the cationic latex emulsion comprises 1% to 5% of the cationic surfactant by weight of the latex particles. [000177] Embodiment 38 provides the cationic latex emulsion of any one of Embodiments 1-37, wherein the cationic latex emulsion comprises 1.5% to 4% of the cationic surfactant by weight of the latex particles. [000178] Embodiment 39 provides the cationic latex emulsion of any one of Embodiments 1-38, wherein the latex particles are 40 wt% to 80 wt% of the cationic latex emulsion. [000179] Embodiment 40 provides the cationic latex emulsion of any one of Embodiments 1-39, wherein the latex particles are 60 wt% to 70 wt% of the cationic latex emulsion. [000180] Embodiment 41 provides the cationic latex emulsion of any one of Embodiments 1-40, wherein the aqueous liquid is 20 wt% to 60 wt% of the cationic latex emulsion. [000181] Embodiment 42 provides the cationic latex emulsion of any one of Embodiments 1-41, wherein the aqueous liquid is 30 wt% to 40 wt% of the cationic latex emulsion. [000182] Embodiment 43 provides the cationic latex emulsion of any one of Embodiments 1-42, wherein the cationic latex emulsion has a viscosity at 25 º C of 1,000 cP to 500,000 cP. [000183] Embodiment 44 provides the cationic latex emulsion of any one of Embodiments 1-43, wherein the cationic latex emulsion has a viscosity at 25 º C of 1,000 cP to 100,000 cP. [000184] Embodiment 45 provides the cationic latex emulsion of any one of Embodiments 1-44, wherein passing the cationic latex emulsion through a 300 micron diameter screen results in less than 0.1 wt% of the cationic latex emulsion remaining on the screen. [000185] Embodiment 46 provides the cationic latex emulsion of any one of Embodiments 1-45, further comprising an acid. [000186] Embodiment 47 provides the cationic latex emulsion of any one of Embodiments 1-46, wherein the acid comprises sulfuric acid, acetic acid, hydrochloric acid, boric acid, phosphoric acid, or a combination thereof. [000187] Embodiment 48 provides a method of forming the cationic latex emulsion of any one of Embodiments 1-47, the method comprising: combining an anionic latex emulsion with the cationic surfactant, the anionic latex emulsion comprising the latex particles, and the aqueous liquid emulsified with the latex particles; and agitating the combination of the anionic latex emulsion and the cationic surfactant to form the cationic latex emulsion of any one of Embodiments 1-47. [000188] Embodiment 49 provides the method of Embodiment 48, wherein agitating comprises agitating the combination of the anionic latex emulsion and the cationic surfactant to increase the viscosity thereof. [000189] Embodiment 50 provides the method of any one of Embodiments 48-49, wherein agitating comprises agitating the combination of the anionic latex emulsion and the cationic surfactant to increase the viscosity thereof until said viscosity becomes stable. [000190] Embodiment 51 provides the method of any one of Embodiments 48-50, wherein the cationic surfactant is combined with the anionic latex emulsion as a solution of the cationic surfactant in a solvent. [000191] Embodiment 52 provides the method of Embodiment 51, wherein the solvent is an alcohol, a diol, water, or a combination thereof. [000192] Embodiment 53 provides the method of any one of Embodiments 51-52, wherein the solvent comprises a (C 1 -C 5 )alkyl alcohol, a di(C 1 -C 5 )alkylene glycol, or a combination thereof. [000193] Embodiment 54 provides the method of any one of Embodiments 51-53, wherein the solvent comprises ethanol, methanol, diethylene glycol, dipropylene glycol, isopropyl alcohol, water, or a combination thereof. [000194] Embodiment 55 provides the method of any one of Embodiments 51-54, wherein the solvent comprises water. [000195] Embodiment 56 provides the method of any one of Embodiments 51-55, wherein the solvent comprises a mixture of water with ethanol, diethylene glycol, or a combination there. [000196] Embodiment 57 provides the method of any one of Embodiments 51-56, wherein the cationic surfactant is about 20 wt% to 80 wt% of the solution of the cationic surfactant in the solvent. [000197] Embodiment 58 provides the method of any one of Embodiments 51-57, wherein the cationic surfactant is about 45 wt% to 60 wt% of the solution of the cationic surfactant in the solvent. [000198] Embodiment 59 provides the method of any one of Embodiments 51-58, further comprising: reacting HOC(O)-R 1 with a compound having the structure to provide a terminal amine having the structure acidifying the terminal amine to provide an ammonium salt; treating the ammonium salt with an epihalohydrin to provide a gamma hydroxy haloammonium salt; and treating the gamma hydroxy haloammonium salt with (R 3 ) 3 N, to provide the cationic surfactant. [000199] Embodiment 60 provides the method of any one of Embodiments 51-59, further comprising: reacting HOC(O)-R 1 with a compound having the structure to provide a terminal amine having the structure acidifying the terminal amine to provide an ammonium salt; treating the ammonium salt with an epihalohydrin to provide a gamma hydroxy haloammonium salt; and treating the gamma hydroxy haloammonium salt with (R 3 ) 3 N, to provide the cationic surfactant. [000200] Embodiment 61 provides the method of any one of Embodiments 51-60, further comprising: acidifying an amine having the structure wherein R 4 is chosen from a substituted or unsubstituted (C 4 -C 22 )alkyl and a substituted or unsubstituted (C 4 -C 22 )alkenyl, wherein R 4 is optionally modified, the modification comprising maleic anhydride modification, polymerization, ene-reaction modified, hydrogenation, isomerization, branching, or a combination thereof. to provide an ammonium salt; treating the ammonium salt with an epihalohydrin to provide a gamma hydroxy haloammonium salt; and treating the gamma hydroxy haloammonium salt with (R 3 ) 3 N, to provide the cationic surfactant. [000201] Embodiment 62 provides an asphalt emulsion comprising the cationic latex emulsion of any one of Embodiments 1-47. [000202] Embodiment 63 provides the asphalt emulsion of Embodiment 62, wherein the asphalt emulsion comprises bitumen, an aqueous liquid, and the cationic latex emulsion of any one of Embodiments 1-47. [000203] Embodiment 64 provides the asphalt emulsion of any one of Embodiments 62-63, wherein bitumen is 1 wt% to 99 wt% of the asphalt emulsion. [000204] Embodiment 65 provides the asphalt emulsion of any one of Embodiments 62-64, wherein bitumen is 50 wt% to 75 wt% of the asphalt emulsion. [000205] Embodiment 66 provides the asphalt emulsion of any one of Embodiments 62-65, wherein aqueous liquid is 0.1 wt% to 50 wt% of the asphalt emulsion. [000206] Embodiment 67 provides the asphalt emulsion of any one of Embodiments 62-66, wherein aqueous liquid is 1 wt% to 40 wt% of the asphalt emulsion. [000207] Embodiment 68 provides the asphalt emulsion of any one of Embodiments 62-67, wherein the cationic surfactant is 0.001 wt% to 50 wt% of the asphalt emulsion. [000208] Embodiment 69 provides the asphalt emulsion of any one of Embodiments 62-68, wherein the cationic surfactant is 0.01 wt% to 20 wt% of the asphalt emulsion. [000209] Embodiment 70 provides the asphalt emulsion of any one of Embodiments 62-69, wherein the cationic latex emulsion is 0.01 wt% to 90 wt% of the asphalt emulsion. [000210] Embodiment 71 provides the asphalt emulsion of any one of Embodiments 62-70, wherein the cationic latex emulsion is 0.1 wt% to 50 wt% of the asphalt emulsion. [000211] Embodiment 72 provides the asphalt emulsion of any one of Embodiments 62-71, wherein the asphalt emulsion is a cationic asphalt emulsion comprising cationic bitumen particles. [000212] Embodiment 73 provides an asphalt emulsion comprising: the cationic latex emulsion of any one of Embodiments 1-47; and cationic bitumen particles. [000213] Embodiment 74 provides a method of forming the asphalt emulsion of any one of Embodiments 62-72, the method comprising: combining a cationic asphalt emulsion with the cationic latex emulsion of any one of Embodiments 1-47, to form the asphalt emulsion of any one of Embodiments 62-72. [000214] Embodiment 75 provides a method of coating a carpet to form a carpet back coating, the method comprising: coating the carpet with the cationic latex emulsion of any one of Embodiments 1-47 to form the carpet back coating thereon. [000215] Embodiment 76 provides a paper coating, tires, asphalt concrete, carpet back coating, latex paint, foam, or ink comprising: the cationic latex emulsion of any one of Embodiments 1-47. [000216] Embodiment 77 provides the cationic latex emulsion, method of forming the cationic latex emulsion, asphalt emulsion, method of forming the asphalt emulsion, method of coating a carpet, or paper coating, tires, asphalt concrete, carpet back coating, latex paint, foam, or ink of any one or any combination of Embodiments 1-76 optionally configured such that all elements or options recited are available to use or select from.