234 DISINFECTION
group, and the other a water-attracting (hydrophilic or polar)
group. Depending on the basis of the charge or absence of
ionization of the hydrophilic group, surface-active agents are
classified into (James, 1965):
1) Anionic agents, which usually have strong deter-
gent, but weak antimicrobial properties, e.g.,
sodium lauryl sulphate.
2) Cationic agents, which have strong bactericidal,
but weak detergent, properties. The term “cationic
detergent” usually signifies a quarternary ammo-
nium compound (QAC, onium compound), but
this is not strictly accurate, as the concentration
at which a QAC is germicidal is so low that its
detergent activity is negligible.
3) Non-ionic agents, which consist of a hydrocar-
bon chain attached to a non-polar water-attracting
group, which is usually a chain of ethylene oxide
units, e.g., cetomacrogols. Non-ionic agents have
no antimicrobial properties.
4) Ampholytic (amphoteric) agents, which are com-
pounds of mixed anionic–cationic character, in
which the charge can be similarly positive and
negative. They are effective antimicrobial com-
pounds, which are extensively used in the dairy
industry.
The QACs are organically substituted ammonium com-
pounds, in which the nitrogen atom has a valency of 5,
four of the substituent radicals (R^1 –R^4 ) are alkyl or het-
erocyclic radicals, and the fifth is a small anion. The sum
of the carbon atoms in the 4R groups is more than 10.
For a QAC to have a high activity, at least one of the four
organic radicals must have a chain length in the range C 8
to C 18. The germicidal activities of the QACs were origi-
nally recognized in 1916, but they did not attain promi-
nence until Domagk’s work in 1935. They are primarily
active against Gram-positive bacteria, with concentrations
as low as about 1 in 200,000 being lethal; higher concentra-
tions ( c. 1 in 30,000) are lethal to Gram-negative bacteria,
although Pseudomonas aeruginosa is highly resistant. The
QACs possess antifungal properties, are sporostatic and
not sporicidal (Russell, 1971) and are inactive against the
tubercle bacillus. Their antimicrobial activity is markedly
affected by organic matter, and they are incompatible with
anionic surface-active agents, some of the non-ionic agents
(such as Lubrols and Tweens) and the phospholipids, e.g.,
lecithin and other fat-containing substances (Russell, 1982;
Russell et al. , 1979). The QACs exert their maximal bac-
tericidal activity under alkaline conditions. Although the
QACs are effective bactericidal and fungicidal agents, it
has been found (Grossgebauer, 1970) that viruses are rather
more resistant than bacteria or fungi.
R^1
R^4 R^3
R^2
N
+
X–
Although several hundred QACs have been prepared
and tested for antimicrobial activity, only a few are regularly
used. These are:
1) Cetrimide (cetyltrimethylammonium bromide,
CTAB), a mixture of dodecyl, tetradecyl- and
hexadecyl-trimethylammonium bromide. In addi-
tion to it uses for pre-operative skin disinfec-
tion and treatment of seborrhoea of the scalp,
cetri mide is also employed, in conjunction with
sodium nitrite, which delays or prevents rusting,
for the storage of sterilized surgical instruments,
although this practice should be discontinued
(Rubbo and Gardner, 1965).
2) Benzalkonium chloride (Zephirol, Zephiran) is
the active constituent of a general purpose and
skin sterilizing agent, “Roccal.” It is also used to
alleviate or prevent napkin rash caused by urea-
splitting organisms, as a preservative in eye-drop
preparations (Pharmaceutical Codex, 1979) and
for the disinfection of blankets.
Other important QACs are domiphen bromide and cetyl-
pyridinium chloride.
The value of QACs in the disinfection of woollen blan-
kets has been observed by various authors (Frisby, 1957;
International Wood Secretariat, 1961), although they cannot be
incorporated in the wash with an anionic compound, because
of incompatibility. In addition, it must be emphasized that res-
idues of anionic agents on blankets from previous washings
could interfere with the action of QACs. To overcome this,
blankets may be washed in an appropriate non-ionic deter-
gent, with a final prolonged rinse in a QAC, or they may be
treated with a non-ionic detergent incorporating a QAC.
The QACs are also of considerable value as disinfectants
in food and dairy plant. If an alkali detergent containing
anionic surface-active wetting agents is used prior to sanitiz-
ing, then utensils and equipment must be thoroughly rinsed
(Barrett, 1969). The QACs at their normally used concentra-
tions are odourless and noncorrosive, but many are not free-
rinsing, and undesirable traces may remain on equipment or
even be present in dairy food (Clegg, 1967, 1970). However,
a combination of a free-rinsing type of QAC and a suitable
non-ionic agent may be usefully employed for washing
instruments and cutlery, etc. (Barrett, 1969).
The cytoplasmic membrane of bacteria and fungi is the
site of action of the QACs. The membrane is composed of
lipoprotein, and it is considered (Russell, 1971) that the lipid
moiety is involved in the lethal action of these compounds
(for more recent information, see Hugo, 1976a,b).
There appears to be a clear relationship between the ther-
modynamic and antibacterial activities of QACs, with solu-
tions having equal antimicrobial activity against an organism
having surface concentration values of the same order of
magnitude. Thermodynamic activities of QACs at two bac-
terial survivor levels (1% and 0.01%) have been shown to
be sufficiently constant (Laycock and Mulley, 1970) to sup-
port the Ferguson (1939) principle that compounds with the
C004_002_r03.indd 234C004_002_r03.indd 234 11/18/2005 10:19:29 AM11/18/2005 10:19:29 AM