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EC number: 629-765-4
CAS number: 1226892-44-9
Due to lack of
quantitative data, absorption rates
recommanded by ECHA guidance are applied.
Available studies do not indicate a
concern for bioaccumulation.
Amidoamine/imidazolines are made from
fatty acid and polyethyleneamines.
The 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 if fatty acids (FA) and ethyleneamines (EA) in the reaction.
The final product is a mixture of
these substances, containing amine-, amide-, and Imidazoline functional
The 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):
The 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 lengths.
The majority is derived from taloil,
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.
Upon 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 substances.
Within 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 by the 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 difference in chain length 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 for all
substances in the AAI group the fatty acid part as similar.
- Polyethyleneamines (EA):
The 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.
Upon 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 determinechemical reactivity and route of
metabolisation, and relate to toxicity.
All 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).
They 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.
The Pow for Tall oil + DETA is 2.2,
which represents the substance with relatively the smallest hydrophilic
part and thus highest Pow value within the group of AAI substance.
As 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 toxicity.
The level of free EA can be of impact,
but as EA are not much more toxic compared to these NOAELs, they are not
likely to be of great importance..
All substances show similar acute oral
toxicity, all with a LD50 > 2000 mg/kg bw. There is a small tendency of
decreased toxicity with increasing size of the EA. All AAI are corrosive
to skin Cat. 1C, and sensitizing to skin. (Possibly the availability of
some free EA could also have some influence here)
Several AAI substances were tested for
genotoxicity, and all 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
Repeated dose studies (combined
repeated dose/reproduction toxicity screening studies or standard 28-day
studies) show the lowest NOAEL of 30 mg/kg bw/day forTO+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 after uptake.
Both Tall oil + TEPA and Tall oil +
PolyEA (containing higher EA) both show a NOAEL of 300 mg/kg bw/day
(showing some small effects, not considered toxicologically relevant).
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.
In 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.
For next phase testing, results from
studies with TO + DETA can be taken as 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 90-day, 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, with low potential of exposure via inhalation due
to very low vapour pressure.
Toxicokinetics, metabolism and
Alkyl 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
this stage no data are available on
dermal absorption. Itis
not expected to easily pass the skin
in view of its ionised form at
on the corrosive properties, dermal
absorption as a consequence of
facilitated penetration through
damaged skin can be anticipated.
Dependent on the solvent and
concentration, up to 60% dermal
absorption might be suggested as a
worst case for assessment purposes
(value taken from the existing EU risk
assessment on primary alkylamines).
Due to the lack of quantitative
absorption data, 50% absorption is
taken as a conservative approach.
for inhalation no data are available
on absorption, and100% is proposed as
worst case. With a vapour pressure
of1.7 x 10-7Pa at 25°C for
DETA based AAI and a boiling
potential for inhalation is limited.
Relevant (in view of possible systemic
absorption) exposures are therefore
only possible as aerosol. If any
inhalation does occur, this can only
be in the form of larger droplets, as
the use does not include fine
spraying. Droplets will deposit mainly
on upper airways, and will be
subsequently swallowed following
mucociliary transportation to pharynx.
This results to no principal
difference in absorption compared oral
via respiratory route is therefore
also set at 100%.
The 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.
The AAI all corrosive to skin, and
toxicity following dermal exposure is characterised by local tissue
damage, rather than the result of percutaneously absorbed material.
Conclusions for read-across:
As explained in this category
justification, for cross-reading in general use can be made of data of
same or lower EA-length where available. Data from Tall oil + DETA
would represent the worst case. This dossier is for the substance
"Fatty acids C18 unsat, reaction products with triethylenetetramine"
(or Tall oil + TETA). As for the substance itself no toxicological
information is available, general cross-reading has been applied to
Tall oil + DETA.
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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