Medical Research Institute

Microbiology department
Biosafety unit

DETERGENTS &
QUATERNARY
AMMONIUM
COMPOUNDS
By Rasha Emad

General terms

Detergent: Product that after formulation is devised

to promote the development of detergency.

Surface Active Agent: Chemical compound which,

when dissolved or dispersed in a liquid is absorbed at
an interface, giving rise to a number of important
chemical properties.

Amphiphilic Product: Product which contains in its

structure one or more hydrophilic groups and one or
more hydrophobic groups.

Detergents

Detergents are organic compounds

comprised of a hydrophobic hydrocarbon
moiety and a hydrophilic charged
headgroup.

When dissolved in water at a given

concentration and temperature, detergent
molecules will form micelles, with the
hydrophobic part in the interior of the
micelle and the headgroup at the exterior.

Mode of action of
detergents

Detergents used in biomedical laboratories

are mild surfactants (=surface acting
agents), used for the disruption of cell
membranes (cell lysis) and the release of
intracellular materials in a soluble form.

Detergents break the protein-protein,

protein-lipid and lipid-lipid associations,
denature proteins and other
macromolecules, prevent unspecific binding
in immunochemical assays and protein
crystallization.

Detergents

A detergent is a surfactant or a mixture of

surfactants with "cleaning properties in dilute
solutions.

Detergents are commonly available as powders or

concentrated solutions. Detergents, like soaps, work
because they are amphiphilic: partly hydrophilic
(polar) and partly hydrophobic (non-polar).

Their dual nature facilitates the mixture

of hydrophobic cpds (oil and grease)
with water. Detergents are also
foaming agents to varying degrees.

Classification of
detergents

Detergents are classified into three broad

groupings, depending on the electrical
charge of the surfactants.
Anionic detergents
Cationic detergents
Nonionic detergents

General structure of detergents

Anionic detergents

Typical anionic detergents are

alkylbenzenesulfonates.

The alkylbenzene portion of theseanionsis

lipophilic
and the sulfonate is hydrophilic.
Two different varieties have been popularized, those
with branched alkyl groups and those with linear
alkyl groups.

Main example is soap

Cationic detergents

Cationic detergents are similar to the

anionic ones, with a hydrophobic
component, but, instead of the anionic
sulfonate group, the cationic surfactants
havequaternary ammoniumas the polar
end.

The ammonium center is positively charged.

Main example is quaternary ammonium

compounds or QACs or Quats

Nonionic detergents

Non-ionic detergents are characterized by

their uncharged, hydrophilic headgroups.

Typical non-ionic detergents are based on

polyoxyethyleneor aglycoside.

Common examples Tween.

Difference between tween 20 &

80

Quaternary ammonium
compounds

Typically known as Quats

Many individual chemicals

Present in thousands of end-use

formulations, many of which are blends
of various Quats

Common uses include disinfectants,

surfactants, fabric softeners, antistatic
agents, and wood preservation

Quaternary ammonium
compounds

They are positively charged

polyatomic ions of the structure NR4+
with R being alkyl or aryl groups.

They are permanently charged,

independent of the pH of their
solution.

Quaternary ammonium
compounds

1.
2.

3.

Each Quat has its own chemical and antimicrobiological characteristics. USEPA has
clustered Quats into four categories:
Group I: The alkyl or hydroxyl (straight chain)
substituted Quats
Group II: The non-halogenated benzyl
substituted
Quats (including hydroxybenzyl,
hydroxyethylbenzyl,
naphylmethyl, dodecyhlbenzhyl, and alkyl
benzyl)
Group III: The di- and tri-chlorobenzyl
substituted

Uses of QUATS

The unique physical/chemical properties of QACs

have resulted in a variety of uses and a high
level of popularity in domestic, agricultural,
health care, and industrial applications such as
surfactants,
emulsifiers,
fabric softeners,
disinfectants,
pesticides,
corrosion inhibitors,
and personal care products.

QUATS as antimicrobials

QACs possess surface-active properties, selfassembly characteristics, detergency, and

antimicrobial properties.
Certain QACs, especially those containing long
alkyl chains, are used as antimicrobials and
disinfectants.
Examples are benzalkonium chloride,
benzethonium chloride, methylbenzethonium
chloride, cetalkonium chloride, cetylpyridinium
chloride, cetrimonium, cetrimide, dofanium
chloride, tetraethylammonium bromide,
didecyldimethylammonium chloride and domiphen
bromide.

QUATS as antimicrobials

Also good against fungi, amoeba, and

enveloped viruses, quats are believed to act
by disrupting the cell membrane.
Quaternary ammonium compounds are
lethal to a wide variety of organisms except
endospores, Mycobacterium tuberculosis
and non-enveloped viruses.

QUATS as antimicrobials

Quats are effective in destroying a broad spectrum of

harmful microorganisms.
They are effective in killing many pathogenic
microorganisms while cleaning the surfaces upon
which they reside all in one simple step.
A few of the microorganisms killed by quat
disinfectants and sanitizers include:
Gram negative and gram positive bacteria like salmonella

typhi, staphylococcus aureus, streptococcus epidermidis,

pseudomonas aeruginosa, and E-coli.
Viruses like HIV-1, Hepatitis B and C, Herpes simplex 1 and 2,
Influenza and Parvovirus Antibiotic resistant strains of
bacteria including methicillin resistant staphylococcus aureus
(MRSA), VRE and many other antibiotic resistant strains.
Fungi like trichophyton interdigitale (athletes foot) and the
fungus that causes ringworm.

Classification of QUATS

QACs can be classified in five major groups

depending on the type of functional groups:
monoalkonium, dialkonium, benzalkonium,
diesteralkonium, and pyridalkonium
halides

QUATS as antimicrobial

They are effective against a variety of

bacteria, fungi, and viruses at very low
concentrations. When QACs are used as
disinfectants, the applied concentration is
typically between 400 and 500 ppm and
almost always below 1000 ppm (e.g., 0.1%
w/v in Lysol).

The most commonly used QACs as bioactive

agents are monoalkonium (C16), dialkonium
(C810), and benzalkonium (C1216)
chlorides

Mode of action of Quats

QACs are lytic bioactive agents.

The main mode of action of QACs against

bacterial cells involves perturbation of the
lipid bilayer of the bacterial cytoplasmic
membrane and the outer membrane of
Gram-negative bacteria.

Such action leads to a progressive leakage

of cytoplasmic components out of the cell
and finally cell lysis.

Health effects of Quats

Quaternary ammonium compounds can display a

range of health effects, amongst which are mild
skin and respiratory irritation up to severe
caustic burns on skin and gastro-intestinal lining
(depending on concentration), gastro-intestinal
symptoms (e.g., nausea and vomiting), coma,
convulsions, hypotension and death.

They are thought to be the chemical group

responsible for anaphylactic reactions that occur
with use of neuromuscular blocking drugs during
general anaesthesia in surgery. Quaternium-15 is
the single most often found cause of allergic
contact dermatitis of the hands

Thank you