Alicyclic amido-quaternary ammonium anti-bacterial agents

#The present invention relates to novel quaternary ammonium compounds represented by the general formula: ##STR1## wherein R is an aliphatic or alicyclic group containing 7-13 carbon atoms, R.sup.2 and R.sup.3 are each methyl or ethyl, R.sup.4 is an aliphatic chain containing 10-18 carbon atoms, n is the integer 2 or 3 and X is a compatible anion such as the halides (Cl.sup.-,Br.sup.-,I.sup.-), sulfates (i.e., methyl sulfate), nitrates, aryl sulfonates, etc. These quaternary compounds possess superior antimicrobial, anticaries, and anticalculus activity.

#The alicyclic group may be any ring system such as the adamantyl radical which is derived from tricyclo-[3.3.1.1.sup.3,7 ]decane showing four fused chair cyclohexane rings as follows: ##STR2## a bicyclo [3.3.0] octane showing two joined pentane rings as follows: the norbornane radical which is represented by the following ring structure: ##STR3## or any other aliphatic ring system containing 7 to 13 carbon atoms.

#Typical examples of the quaternary ammonium compounds which may be used in this invention are:

#______________________________________ % ______________________________________ 3-Decaneamidopropyldimethyltetradecyl ammonium chloride 0.50 Nonionic detergent* 1.00 Glycerine 22.00 Sodium pyrophosphate 0.25 Carboxymethyl cellulose 0.85 Sodium saccharin 0.20 Sodium benzoate 0.50 Calcium carbonate (precipitated) 5.00 Dicalcium phosphate dihydrate 46.75 Flavor 0.80 Water 22.15 ______________________________________ *Tween 80-Polyoxyethylene (20 moles ethylene oxide) sorbitan monooleate.

#______________________________________ % ______________________________________ Quaternary ammonium amide of adamantane carboxylic acid 0.025 Nonionic detergent (Pluronic F-68)* 1.00 Ethyl alcohol (containing flavor) 15.00 Glycerine 10.00 Saccharin 0.02 Water 73.73 ______________________________________ *Block polymer of 80% polyoxyethylene and 20% polyoxypropylene.

#The quaternary ammonium amides of instant invention can be prepared by a two-step method of reacting a carboxylic acid, ester or acid chloride with N,N-dialkylethylene diamine or N,N-dialkylpropylene diamine to form a tertiary amino amide and subsequently quaternizing with an alkyl halide or ester of sulfuric or of arenesulfonic acid (i.e., methyl p-toluenesulfonate) as illustrated by the following equations wherein R, R.sup.2, R.sup.3, R.sup.4 have the aforedefined meanings. ##STR5##