Fluorinated quaternary ammonium compounds, processes for their preparation and their use as drag reducing agents

Abstract

Abstract 1. A quaternary ammonium compound of the formula R-K**+ A**- in which R denotes n-fluoroalkyl, n-fluoroalkenyl, n-alkyl, n-alkenyl or a group of the formula see diagramm : EP0149172,P20,F6 or Rf -(CH2 )y B(CH2 )x - Rf denotes n-fluoroalkyl or n-fluoroalkenyl, R1 denotes hydrogen, methyl or ethyl, x denotes an integer from 2 to 6, y denotes 0, 1 or 2, B denotes an oxygen or sulfur atom, K**+ denotes a cation of the formula see diagramm : EP0149172,P20,F7 or see diagramm : EP0149172,P20,F8 R2 denotes hydrogen, C1 -C4 -hydroxyalkyl, C1 -C5 -alkyl, benzyl or phenyl, R3 denotes hydrogen, methyl or ethyl, the radicals R4 , which can be identical or different, in each case denote hydrogen or C1 -C3 -alkyl and, in the case of the fluorinated groups R, A**- denotes an n-alkyl-, n-alkenyl- or n-fluoroalkyl-sulfonate anion, an n-alkyl-, n-alkenyl- or n-fluoroalkenyl-carboxylate anion, a benzoate, phenylsulfonate, naphthoate or thiocyanate anion or an anion of the formula Cn Cl2n+1 COO**- , where n = 1, 2 or 3, or, in the case of the non-fluorinated groups R, A**- denotes an n-fluoroalkyl- or n-fluoroalkenyl-carboxylate anion or an n-fluoroalkylsulfonate or n-fluoroalkenylsulfonate anion, the compounds being excluded in the cases where R = fluoroalkyl, fluoroalkenyl and K**+ = trialkylammonium and A**- = alkylsulfonate, alkenylsulfonate, phenylsulfonate, acetate ; R = alkyl, K**+ = N**+ H3 and A**- = fluoroalkylcarboxylate ; and R-K**+ = (C1 -C2 )-trialkylammonium and A**- = fluoroalkylsulfonate or fluoroalkylcarboxylate ; and also the salts of the formula see diagramm : EP0149172,P20,F1 where n = 12-14 and x = 1-3.

Inventors

• 👤 Dieter Dr. Ohlendorf
• 👤 Werner Dr. Interthal
• 👤 Heinrich Dr. Bathelt
• 👤 Heinz Prof. Dr. Hoffmann

Bibliographic Details