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Harmful influence of cyclic
compound ingredients in
detergents
Semira Hajrlahović Mehić, M. Sc.
Inspector counselor
Ministry of Health of Republic of Slovenia
Chemicals Office of the Republic of Slovenia
1
Synthetic detergent : Compositions
Constituent
Composition (%)
Sodium tripolyphosphate (water softener, loosens dirt) a
38.0
Sodium alkane sulphonate (surfactant)
25.0
Sodium perborate tetrahydrate (oxidising agent)
25.0
Soap (sodium alkane carboxylates)
3.0
Sodium sulphate (filler, water softener)
2.5
Sodium carboxymethyl cellulose (dirt-suspending agent)
1.6
Sodium metasilicate (binder, loosens dirt)
1.0
Bacillus protease
0.8
Fluorescent brighteners
0.3
Foam-controlling agents
Trace
Perfume
Trace
Water
to 100%
2
Surfactant
• The term comes from the words surface active
agent
• One of many compounds in detergent
• In detergents are added to remove dirt
• Also used extensively in industry
3
Surfactant function
• To breaking down the interface between water and
oils and/or dirt
• To hold oils/dirt in suspension, and allow their
removal
• Contain both:
– a hydrophilic („water loving“) group, such as an acid
anion, (-CO2- or SO3-) and
– a hydrophobic („water hating“) group, such as an alkyl
chain
4
Action of a surfactant
5
Soaps
• The earliest surfactants
• Process known as saponification
– The glycerides are hydrolyzed by heating with sodium
hydroxide solution to form soaps, the sodium salts of the
acids, and propane-1,2,3-triol
6
Soaps in water
• Soaps form insoluble calcium and magnesium
salts with the Ca and Mg ions in hard water
→ much of the soap is wasted forming an
insoluble scum
7
Syntethic surfactants
• Synthetic surfactants have one very important
advantage over soaps: solubility
• This is avoid by using a synthetic surfactant
– where e.g. the carboxylate group in soap is
replaced by a sulfonate/sulfate group as the
hydrophilic part
→ Ca and Mg salts are more soluble in
water
8
Syntethic surfactants
• The glycerides used to make surfactants contain
saturated and unsaturated carboxylic acids
• No. of carbon atoms within the range 12-20
• Octadecanoic acid (Stearic acid; C18)
(saturated)
• Dodecanoic acid (Lauric acid; C12)CH3
(saturated)
• Tetradecenoic acid (Miristoleic acid;
C14:1) (unsaturated)
9
Syntethic surfactants;
classification
• Based upon the nature of the hydrophilic
"head-groups" as:
• Anionics
• Nonionics
• Cationics
• Amphoterics
10
Anionics
• The hydrophilic group is negatively charged
• The most widely used type of surfactants for
laundering, dishwashing liquids and shampoos
• They are particularly good at keeping the dirt,
once dislodged, away from fabrics.
11
Anionics types
•
•
•
•
4 anionic groups are used:
Alkylbenzene sulfonates
Alkyl sulfates
Alkyl ether sulfates
Soaps
12
Anionics: Alkylbenzene sulfonates
• The most common synthetic anionic
surfactants are based on the straight chain
alkylbenzene sulfonates (LAS; LABSA, ABS)
• Benzene is mixed with an alkene or
chloroalkane in the presence of an acid
catalyst
13
Anionics: Alkylbenzene sulfonates
• Most sodium dodecylbenzenesulfonates are a
member of the linear alkylbenzenesulfonates
– the dodecyl group (C12H25) is unbranched
– 4-(5-Dodecyl) benzenesulfonate
(4 indicating the position of the benzene ring, 5 indicating the position on the
dodecane chain)
14
Anionics: Alkylbenzene sulfonates
• Branched isomers (derived from tetramerized
propylene) are also known but are not as
widely used because they biodegrade too
slowly
– And lead to foaming in rivers
and sewage plants
• In EU the surfactant must have unbranched
side chains which degrade more rapidly
15
Harmful hazards of Alkylbenzene sulfonates
16
Anionics types
•
•
•
•
Alkylbenzene sulfonates
Alkyl sulfates
Alkyl ether sulfates
Soaps
17
Anionics: Alkyl sulfates
• Are in many detergents, particularly liquids
• Alkyl sulfates = esters of linear alcohols (C10C18) and sulfuric acid
– manufactured by treating the alcohol with SO3
• Also used in personal care products
(toothpaste)
18
19
Alkyl sulfates v.s. Alkylbenzene sulfonates
• Sodium dodecyl sulfate (Sodium lauryl sulfate)
• Sodium dodecylbenzenesulfonate
20
Anionics types
•
•
•
•
Alkylbenzene sulfonates
Alkyl sulfates
Alkyl ether sulfates
Soaps
21
Anionics: Alkyl ether sulfates
• More widely used than alkyl sulfates are
sodium alkyl ether sulfates (e.g.SLES)
22
Anionics: Alkyl ether sulfates
• Preferred by product formulators for many
applications (dishwashing liquids, shower gels,
shampoo, etc)
• Are milder to the skin than alkyl sulfates
• Also generate less foam
– an advantage in the formulation of laundry
machine products
23
24
Anionics types
•
•
•
•
Alkylbenzene sulfonates
Alkyl sulfates
Alkyl ether sulfates
Soaps
25
Syntethic surfactants;
classification
• Based upon the nature of the hydrophilic
"head-groups" as:
• Anionics
• Cationics
• Nonionics
• Amphoterics
26
Cationic
• Hydrophilic head is positively charged
• Produced in much smaller quantities than the
anionics,
• Several types, each used for a specific purpose
– Mono alkyl quaternary systems
– Esterquats
27
Cationic
Mono alkyl quaternary systems
• Alkyl quaternary nitrogen system has alkyl groups
attached to the nitrogen atom
• Used as fabric softeners with anionic
surfactants, helping them to break down the
interface between the dirt/stain and the water
28
Cationic: Esterquats
• Give detergents their fabric softening qualities
• Are ester linkage between the alkyl chains and
the quaternary head-group as these are more
biodegradable and less toxic
29
Syntethic surfactants;
classification
• Based upon the nature of the hydrophilic
"head-groups" as:
• Anionics
• Cationics
• Nonionics
• Amphoterics
30
Nonionics
• Do not bear an electrical charge and are often used
together with anionics
• An advantage: do not interact with Ca and Mg ions in
hard water
• Nearly 50% of surfactant production (excluding soap)
• The major group: ethoxylates made by
condensing long chain alcohols with ethylene
oxide to form ethers
31
Nonionics
• More surface active and better emulsifiers than
anionics at similar concentrations
• Less soluble than anionics in hot water and produce
less foam
• They are also more efficient in removing oily and
organic dirt than anionics.
• Used in fabric washing detergents (both powders and
liquids)
• Active in cold solution and useful:
– where is a lack of hot water supplies
– where a desire to lower the wash temperatures
32
Nonionic
Nonylphenol ethoxylates (NPE)
• The restrictions on the marketing and use of
NP and NPE are described in Annex XVII, no.
46 to the REACH ( Reg. (EC) No 1907/2006):
• NP and NPE shall not be placed on the market,
or used, as substances or in mixtures in
concentrations equal to or greater than 0,1%
by weight for the certain purposes:
– also industrial and institutional
– domestic cleaning
33
Nonionic
Nonylphenol ethoxylates (NPE)
• The restrictions of NP and NPE are based on a
need to limit the use of these substances as:
– NPE are degraded to nonylphenols, which
are considered to be endocrine disrupters
– NPE are not degradable rapidly in the
environment
34
35
Syntethic surfactants;
classification
• Based upon the nature of the hydrophilic
"head-groups" as:
• Anionics
• Cationics
• Nonionics
• Amphoterics
36
Amphoterics
• Amphoteric (or zwitterionic) „head-group“
carries both a negative and positive charge
• A range of methods to produce amfotercs ,
almost all contain a quaternary ammonium
ion (a cation)
• The negatively charged group can be:
– carboxylate ( -CO2-)
– sulfate ( -OSO3-) or
– sulfonate (-SO3)
37
Amphoterics: Betaines
• A well-used class is the alkyl betaines with carboxyl group
• Betaines are neutral compounds with a cationic and an
anionic group which are not adjacent to one another
• Betaines are neutral compounds with a cationic and an
anionic group which are not adjacent to one another
• Very mild and used in shampoos and other cosmetics
• pH balanced
38
39
Synthetic detergent : Compositions
Constituent
Composition (%)
Sodium tripolyphosphate (water softener, loosens dirt) a
38.0
Sodium alkane sulphonate (surfactant)
25.0
Sodium perborate tetrahydrate (oxidising agent)
25.0
Soap (sodium alkane carboxylates)
3.0
Sodium sulphate (filler, water softener)
2.5
Sodium carboxymethyl cellulose (dirt-suspending agent)
1.6
Sodium metasilicate (binder, loosens dirt)
1.0
Bacillus protease
0.8
Fluorescent brighteners
0.3
Foam-controlling agents
Trace
Perfume
Trace
Water
to 100%
40
Sodium perborate tetrahydrate
• Oxidising agent
– It serves as a source of active oxygen in many
laundary detergents,cleaning agents….
41
Classification according to part 3 of Annex VI, Table 3.1 of Regulation (EC)
No 1272/2008
42
43
Conclusions
• Not many cyclic compound are ingredients in
detergents/ cleaning agent
• Concentrations: low
• However substances as such have hazardous
properties
– human health
– environment
• Restrictions in force for some surfactants in EU
44
Thank you for your attention
[email protected]
45