Oxyalkylated quaternary ammonium compounds and their use as drag reducing agents
AssigneeHoechst Aktiengesellschaft
InventorsDieter Ohlendorf, Manfred Hofinger
Life of this patent
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Abstract
Quaternary ammonium compounds of the formula ##STR1## in which R.sub.1 denotes an alkyl or alkenyl radical with 12 to 22 carbon atoms; R.sub.2 and R.sub.3 are identical or different and denote an alkyl radical with 1 to 4 carbon atoms; x denotes an integral or non-integral number from 1 to 3; and A.sup..crclbar. denotes an alkyl- or alkenyl-sulfonate anion, an alkyl or alkenyl-carbonate anion or a benzoate, naphthoate or phenylsulfonate anion, the tosylate ion being excluded, a process for their preparation and their use as drag reducing agents in liquids with turbulent flow.
Claims7
A quaternary ammonium compound of the formula ##STR9## in which R.sub.1 denotes an alkyl or alkenyl radical with 12 to 22 C atoms;
- R.sub.2 and R.sub.3 are identical or different and denote an alkyl radical with 1 to 4 C atoms;
- x denotes an integral or non-integral number from 1 to 3;
- and
- A.sup..crclbar. denotes a straight-chain C.sub.6 -C.sub.9 -alkyl-sulfonate or C.sub.6 -C.sub.9 -alkenylsulfonate anion, wherein the sum of the carbon atoms in R.sub.1 and in the sulfonate anion should be at least 21, a straight-chain C.sub.6 -C.sub.9 -alkylcarboxylate or C.sub.6 -C.sub.9 -alkenylcarboxylate anion, wherein the sum of the carbon atoms in R.sub.1 and in the carboxylate anion should be at least 23, the salicylate anion or an anion of the formulae ##STR10## in which R.sub.6 denotes --COO.sup.- or --SO.sub.3.sup.-, R.sub.7 denotes hydrogen, hydroxyl in position 2 or 3 relative to R.sub.6, or NO.sub.2, fluorine, chlorine, bromine or iodine in position 3 relative to R.sub.6, R.sub.8 denotes C.sub.1 -C.sub.5 -alkeyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.1 -C.sub.5 -alkoxy in position 3, 4 or 5 relative to R.sub.6, and R.sub.9 denotes hydrogen or methyl, except that, in formula (I), R.sup.7 is not hydrogen if R.sub.8 is methyl and R.sub.6 is --SO.sup.-.sub.3.
A compound of the formula ##STR13## in which x denotes an integral or non-integral number from 1 to 1.5, n denotes a number from 12 to 24 and A.sup..crclbar. denotes an anion from the group
- (a) C.sub.6 H.sub.13 SO.sub.3.sup.- for the case where n=20-24,
- (b) C.sub.7 H.sub.15 SO.sub.3.sup.- for the case where n=14-22,
- (c) C.sub.8 H.sub.17 SO.sub.3.sup.- for the case where n=14-20,
- (d) 2-phenylsulfonate, m-halogenobenzoate or salicylate,
- (e) an anion of the formula ##STR14## where R.sub.6 =SO.sub.3.sup.- or COO.sup.- and R.sub.10 =C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
- (f) 2-hydroxy-1-naphthoate, 3-(or 4) -hydroxy-2-naphthoate and the corresponding naphtholsulfonic acid anions, the tosylate ion being excluded.
A quarternary ammonium compound of the formula ##STR15## in which R.sub.1 denotes an alkyl or alkenyl radical with 12 to 22 C atoms;
- R.sub.2 and R.sub.3 are identical or different and denote an alkyl radical with 1 to 4 C atoms;
- x denotes an integral or non-integral number from 1 to 3;
- and A.sup.- denotes an anion of the formulae ##STR16## wherein R.sup.* is hydrogen, C.sub.1 -C.sub.5 -alkoxy.
Dependencies are inferred from the claim text.