Alkyldimethylbenzylammonium chloride

Dextran [9004-54-0] Mf 6,000-220,000. Solutions keeps indefinitely at room temperature if 0.2mL of Roccal (10% alkyldimethylbenzylammonium chloride) or 2mg phenyl mercuric acetate are added per lOOmL solution. [Scott and Melvin Anal Biochem 25 1656 7955.]... 

Other groups, such as quaternary ammonium compounds [quats or alkyldimethylbenzylammonium chloride (ADBAC)] may have hundreds of variants, produced by many manufacturers located around the globe. 

The compounds based on alkyldimethylbenzylammonium chloride type have been used as laundry disinfecting agents. They show hmited fabric softening character [4]. 

Benzalkonium chloride is composed of a mixture of alkyldimethylbenzylammonium chlorides. The hydro-phobic alkyl residues are paraffinic chains with 8-18 carbon atoms. Benzalkonium chloride is used as a preservative in suspensions and solutions for nasal sprays and in eye-drops. Depending on the concentration of the solution, local irritant effects can occur. In nasal sprays it can exacerbate rhinitis (1) and in eye-drops it can cause irritation or keratitis (2). 

FIGURE 6.14 Organic formulas of the following cationic hpids (1) benzaUconium chloride (alkyldimethylbenzylammonium chloride, BA) (2) cetrimide (tetradecyltrimethylammonium bromide, CTAB) (3) cetylpyridinium chloride (hexadecylpyridinium chloride, CPC) (4) dimethyldioctadecylammonium bromide (DDAB) (5) N,N-di-( 3-stearoylethyl)-N,N-dim-ethyl-ammonium chloride (Esterquat lEQ) (6) N-[l-(2,3-dioleoyloxy)propyl]-N,N,N-trime-thylammonium chloride (DOTAP). 

In 1935, almost 20 years after the introduction of these relatively simple aliphatic QACs, Dormagk reported that the substitution of a benzyl group on the quaternary nitrogen increased antibacterial activity [3]. This second type of QAC, namely alkyldimethylbenzylammonium chlorides (ADBACs), were the first class of QAC to find acceptance and utilization as disinfectants in medical applications. 

Further experiments with bacteria reveal the dependence of activity on chain length of alkyldimethylbenzylammonium chlorides [25]. Table 1 summarizes these results, (Fig. 2) showing that as chain length increases from Cs to Cm, activity increases. However, as chain length increases beyond this point, activity decreases. 

Table 1 Effect of Chain Length of Alkyldimethylbenzylammonium Chlorides on Minimal Inhibitory Concentration... 

FIGURE 1. Structure of a typical cationic detergent antibacterial agent. A mixture of alkyldimethylbenzylammonium chlorides of the general formula in which R represents a mixture of the alkyls from CgHav to C18H37. 

Cutler, R. A., Cimijotti, E. B., Okolowich, T. J. Wetterau, W. F. (1966). Alkyldimethylbenzylammonium chlorides — a comparative study of the odd and even chain homologues. CSMA Proceedings of the 53rd Annual Meeting, pp. 102-13. 

Quats are included in the list of surfactants for EOR, but technically they are used in other oil field operations, particularly in drilling muds. Their cationic nature, ability to emulsify oils plus potent germicidal activity make quats uniquely useful in mineral processing and oil applications. There is an abundance of environmental data on quats, not because of oil field operations, but rather because of their use as fabric softeners in detergents. The best known fabric softener and antistatic agent is ditaUow dimethyl ammonium chloride (DTDMAC). Emulsifiers commonly have a N-alkyltrimethylammonium chloride or N-alkylimidazoline chloride configuration, and germicides, such as benzalkonium chloride, typically have a N-alkyldimethylbenzylammonium chloride structure. The fate and effects of these multifunctional surfactants are detailed in several reviews [9, 55, 60, 61]. 

Enhancement in percutaneous penetration is overall modest MW molecular weight, ADBAC alkyldimethylbenzylammonium chloride... 

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