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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