Methods of making an antistatic agent

A method for making the phosphonium sulfonate salt of generic formula (1):

• wherein each X is independently a halogen or hydrogen, provided that the molar ratio of halogen to hydrogen is greater than about 0.90;
• p is 0 or 1 and q and r are integers of 0 to about 7 provided that q+r is less than 8 and that if p is not zero then r is greater than zero;
• and each R is the same or different hydrocarbon radical containing 1 to about 18 carbon atoms, the method comprising
• combining, in an aqueous medium, a compound of the generic formula (4)
• wherein X, p, q, and r have the same meanings as in formula (1), with a compound of the generic formula (5):
• (R)4P—OH (5)
• wherein R has the same meaning as in formula (1);
• and,
• separating the phosphonium sulfonate product of formula (1).

A method for making the phosphonium sulfonate salt of generic formula (1):

• wherein each X is independently a halogen or hydrogen, provided that the molar ratio of halogen to hydrogen is greater than about 0.90;
• p is 0 or 1 and q and r are integers of 0 to about 7 provided that q+r is less than 8 and that if p is not zero then r is greater than zero;
• and each R is the same or different hydrocarbon radical containing 1 to about 18 carbon atoms, the method comprising
• combining in an aqueous medium
• sodium hydroxide and/or lithium hydroxide;
• a compound of the generic formula (4):
• wherein X, q, p, and r are as defined above;
• and
• a compound of the generic formula (3):
• (R)4P-Z (3)
• wherein Z is a halogen and R is as defined above;
• and
• separating the phosphonium sulfonate of formula (1).