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EC number: 629-732-4
CAS number: 1224966-13-5
are made from fatty acid and polyethyleneamines.
manufacturing process is a one-step process with formation of amide
and imidazoline structures. To promote imidazoline formation from the
amide, the reaction mixture is heated to temperatures above 180ºC. The
resulting product therefore is a mixture of the amide structure of the
fatty acid and the polyethyleneamine and its imidazoline. Also is
possible that two fatty acid molecules bind at each end of the
polyethyleneamine resulting todi-substituted amine or imidazoline.
This can be influenced by the ratio of fatty acids (FA) and
ethyleneamines (EA) in the reaction.
final product is a mixture of these substances, containing amine-,
amide-, and imidazoline functional groups.
members of this category can be characterised by their starting
materials: the hydrophobic part from fatty acids and the hydrophilic
part from the polyethyleneamines:
Fatty acids (FA):
difference in alkyl chain length distribution is limited among the
members of this category. The sources are indicated as tall oil,
vegetable oil, rape oil, C12-18 and C18-unsaturated fatty acids and
tallow. All of these consist of predominantly C16 and C18 alkyl chain
majority is derived from tall oil, basically consisting of C18 and
some C16. Some of the substances refer to another source in their name
as vegetable oil or tallow, but even then the actual composition could
show the same chain length distribution as tall oil.
harmonization of the use of names and CAS numbers within this category
this has lead to some renaming and use of different CAS numbers
compared to what was reported in earlier study reports for those
a specific structure, the variability of the alkyl chain length is
considered to have a possible modifying activity, which is related to
modification of the physiological properties of the molecule with
increase or shortening of the apolar alkyl chain part. This is
suspected to influence aspects related to bioavailability, but not
aspects of chemical reactivity and route of metabolisation, aspects
that influence specific mechanisms of toxicity such as sensitisation
and genotoxicity and are more related to the hydrophilic part. As the
differences in chain lengths are only very minimal as all substances
basically contain C16 and C18 alkyl chains, it seems justified from a
toxicological point of view to consider the fatty acid part as similar
for all AAI substances.
chain length of the polyethyleneamines used for the production of the
various Amidoamines/imidazolines in this category can vary. In order
of increasing EA length, ranging from DETA (diethylenetriamine), TETA
(triethylenetetramine), TEPA (tetraethylenepentamine), PEHA
(pentaethylenehexamine) and higher, generally denoted as
polyethyleneamines (PolyEA). Although some products are derived from
the use of basically one specific ethyleneamine, often a mixture of
ethyleneamines of different lengths are used.
the binding of the fatty acids with the amines of the EA, this results
to a mixture of these substances, containing amine-, amide-, and
imidazoline functional groups. These groups determine chemical
reactivity and route of metabolisation, and relate to toxicity.
substances within the AAI group show the same reactive groups, show
similar composition of amide, imidazoline, and some dimer structures
of both, with the length of original EA amines used for production as
biggest difference. The range of molecular weights among the AAI
substance are very similar, with a range from about 100 to 600 (for
Tall oil + DETA) up to 100 to 900 (for Tall oil + polyamines) in case
of use of larger ethyleneamines. Other physico-chemical properties
also show very little variation: They are all (somewhat viscous)
liquids, with a melting point below -15 ºC or lower (generally < -30
ºC), a boiling point above 300 ºC, and a very low vapour pressure
(0.00017 mPa at 25°C for Tall oil + DETA).
are surface active with surface tension about 30-35 mN/m for aqueous
concentrations above CMC. For DETA, TETA and HEPA based AAI, are the
CMC resp. 99, 19 and 15 mg/L.
Pow for Tall oil + DETA is 2.2, which representing the substance with
relatively the smallest hydrophilic part and thus highest Pow value
within the group of AAI substance.
indicated above, the substances within the group of AAI are all very
much alike, and show the same reactive groups. The major difference is
related to the length of the ethyleneamines used for the production.
Available data from repeated dose studies performed on various
representative substances over the group of AAI indicates that
toxicity decreases with increasing length of EA groups. The level of
formed imidazoline compared to imidazoline seems to be of no
consequence for the toxicity. Data from study on a substance
consisting of only Amidoamine and no imidazoline resulted to the same
level of free EA can be of impact, but as EA are not much more toxic
compared to the NOAELs obtained for these AAI products, it cannot have
a large impact.
substances show similar acute oral toxicity, all with a LD50 > 2000
mg/kg bw. There is possibly a small tendency of decreased toxicity
with increasing size of the EA. All AAI are corrosive to skin Cat. 1C,
and sensitizing to skin. (The presence of some free EA in teh products
could also have some influence here)
AAI substances were tested for genotoxicity, and all that were tested
were not mutagenic in bacterial mutagenicity study (Ames test),
induced no chromosomal aberrations in human lymphocytes, and were not
mutagenic in mouse lymphoma cells. AAI substances in general therefore
need not be classified for genotoxicity
dose studies (combined repeated dose/reproduction toxicity screening
studies or standard 28-day studies) show the lowest NOAEL of 30 mg/kg
bw/day for TO+DETA, based on an increased incidence/severity of
macrophage foci in the mesenteric lymph node. This could be related to
the route of application and to the irritant effect of the test item
Tall oil + TEPA and Tall oil + PolyEA (containing higher EA) show a
NOAEL of 300 mg/kg bw/day (showing some small effects, not considered
reproductive or developmental toxicity was observed in an OECD 422
screening study with Tall oil diethylenetriamine imidazoline. Similar
OECD 422 studies have been performed on AAI based on TEPA and PolyEA,
and have also shown no indication of concern for reproductive or
developmental toxicity up to the highest dose tested.
conclusion: It seems that lower EA results to higher toxicity, and
that the forming of imidazoline itself does not play a significant
role. For cross-reading in general use is made with data of same or
lower EA-length where available, and that of Tall oil + DETA
representing the worst case.
next phase testing, results from studies with TO + DETA can be
regarded as the worst case assumption for all others substances in the
AAI category. Consequently, only studies on Tall oil + DETA are
proposed for the next phase, and include a 90-day study, and a
developmental toxicity study. In view of the total lack of effects on
reproduction in all three of the performed reproduction toxicity
screening studies, a 2-generation study is not considered to provide
useful additional information. In addition the low likelihood of
exposure can be considered as these substances are only applied in
professional or industrial setting applying adequate PPE, due to
corrosive properties, and with low potential of exposure via
inhalation due to very low vapour pressure.
metabolism and distribution
amidoamine/imidazolines are mainly protonated under environmental
conditions. The protonated fraction will behave as salt in water. AAI
are surface active and have a low solubility in the form of CMC. For
DETA, TETA and HEPA based AAI, the observed CMC were resp. 99, 19 and
15 mg/L. The actual dissolved concentration in water will be extremely
low as alkyl amidoamines/imidazolines will sorb strongly to sorbents.
As a consequence, absorption from gastro-intestinal system is likely
to be slow.
mode of action of for AAI follows from its structure, consisting of an
apolar fatty acid chain and a polar end of a primary amine from the
polyethyleneamine. The structure can disrupt the cytoplasmatic
membrane, leading to lyses of the cell content and consequently the
death of the cell.
AAI all corrosive to skin, and toxicity following dermal exposure is
characterised by local tissue damage, rather than the result of
percutaneously absorbed material.
properties of AAI indicate a low likelihood for exposure via
inhalation, with a boiling point > 300 °C and very low vapour pressure
(0.00017 mPa at 25°C for DETA based AAI).
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.Reproduction or further distribution of this information may be subject to copyright protection. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner.
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