Title of Invention

A FUEL COMPOSITION

Abstract A fuel composition with a sulphur content of less than or equal to 500 ppm, and comprising at least one additive, characterized in that the additive is composed of: from 5 to 25% by weight of at least one glycerol monoester of formulae (IA) and/or (IB) below: with R1 chosen from saturated or unsaturated, linear or slightly branched, alkyl chains comprising from 8 to 24 carbon atoms and cyclic and polycyclic groups comprising from 8 to 60 carbon atoms, • from 35 to 75% by weight of at least one compound of formula (II) below: in which R2 is a saturated or unsaturated, linear or slightly branched, alkyl chain comprising from 8 to 24 carbon atoms, and X is chosen from (i) the groups ORo, Ro being a hydrocarbon residue comprising from 1 to 8 carbon atoms, optionally substituted by one or more ester groups, and (ii) the groups deriving from primary and/or secondary amines or from alkanolamines with a linear or branched aliphatic hydrocarbon chain comprising from 1 to 18 carbon atoms, • from 0.1 to 20% by weight of at least one glycerol diester of formula (IIIA) and/or (IIIB): in which R3 and R4 are identical or different and are chosen from saturated or unsaturated, linear or slightly branched, alkyl chains comprising from 8 to 24 carbon atoms and cyclic and polycyclic groups comprising from 8 to 60 carbon atoms.
Full Text FUEL LUBRICITY ADDITIVE
The present invention relates to a fuel contain-
ing a lubricity additive for improving the lubrication
properties of fuels, whether ground vehicle engine fuel
(diesel) or jet fuel, and more particularly of diesel
fuels with a low sulphur content.
It is well known that diesel fuels and jet fuels
must have lubricating capabilities, for the protection of
pumps, injection systems and any moving part with which
these products come into contact in an internal
combustion engine. With the intention of employing
products which are increasingly pure and non-polluting,
in particular devoid of sulphur, the refining industry
has been led increasingly to improve its treatment
processes for the removal of sulphur compounds. However,
it has been observed that on losing sulphur compounds,
the aromatic and polar compounds often associated were
also lost, which caused a loss in the lubricating power
of these fuels. Thus, beyond certain contents, the
elimination of sulphur compounds from the composition of
these products very substantially promotes the phenomena
of wear and of failure of moving components in pumps and
in injection systems. As regulations in many countries
have imposed a limitation on the acceptable upper content
of sulphur compounds in fuels of 0.05% by weight, in
order to lower the emissions of polluting combustion
gases from cars, lorries or buses, especially in urban
built-up areas, these lubricating compounds must be
replaced by other compounds which are non-polluting with
regard to the environment but exhibit a sufficient
lubricating power to avoid the risks of wear.
The literature also mentions that petrol fuels
with a low sulphur content have a lubricating power which
can prove to be insufficient to ensure good lubrication
of the injection systems in new vehicles and can bring
about a premature risk of wear.
Several types of additives have already been
provided in order to solve this problem. Thus, antiwear
additives have been added to diesel fuels, some of these
additives being known in the field of lubricants, of the
type of unsaturated fatty acid dimers and fatty acid
esters, aliphatic amines, esters of fatty acids and of
diethanolamine, and long-chain aliphatic monocarboxylic
acids, such as described in Patents US 2,527,889, US
4,185,594, US 4,204,481 and US 4,208,190. The majority of
these additives exhibit a sufficient lubricating power
but at concentrations which are much too high, which is
very unfavourable economically for purchasing. In addi-
tion, additives containing dimeric acids, like those
containing trimeric acids, cannot be employed in fuels
feeding vehicles in which the fuel can be in contact with
the lubricating oil, because these acids form, by chemi-
cal reaction with the detergents usually employed in
lubricants, deposits which can accelerate the wear
processes.
Patent US 4,609,376 recommends the use of
antiwear additives obtained from esters of mono- and
polycarboxylic acids and of polyhydroxylated alcohols in
fuels containing alcohols in their composition.
In Patent GB 2,307,246, the product resulting
from the reaction of carboxylic acid containing 10 to 60
carbon atoms, chosen from fatty acids or fatty acid
dimers, with an alkanolamine, obtained by condensation of
an amine or of a polyamine with an alkylene oxide, is
preferred as lubricity additive.
It is preferable, in Patent GB 2,307,247, to
employ an acid derivative, substituted by a least one
hydroxyl group or one ester of polyols, or alternatively
an amide of this acid.
Another route chosen is to introduce vegetable
oils or their esters into the fuels, in order to improve
their lubricating power or their lubricity. These include
rapeseed, linseed, soybean and sunflower oils or their
esters (see Patents EP 635,558 and EP 605,857). However,
one of the major disadvantages of these esters is their
low lubricating power at a concentration of less than
0.5% by weight in the fuels.
The present invention aims to solve the problems
encountered with the additives provided by the prior art,
that is to say to improve the lubricating power of the
desulphurized and partially dearomatized fuels, while
remaining compatible with the other additives, in par-
ticular detergents, and the lubricating oils, in par-
ticular in not forming deposits, and while reducing the
cost price, in particular by a lower additive content of
markedly less than 0.5%.
The subject of the present invention is the use
as lubricity additive for improving the lubricating power
of diesel and aviation fuels with a low sulphur content,
that is to say with a sulphur content of less than or
equal to 500 ppm, characterized in that the additive is
composed of:
1) from 5 to 25% by weight of at least one
glycerol monoester of following formula (IA) or (IB):

with Rx chosen from saturated or unsaturated,
linear or slightly branched, alkyl chains comprising from
8 to 24 carbon atoms and cyclic and polycyclic groups
comprising from 8 to 60 carbon atoms,
2) from 3 5 to 75% by weight of a compound of
formula (II) below:

in which R2 is a saturated or unsaturated, linear or
slightly branched, alkyl chain comprising from 8 to 24
carbon atoms or a cyclic or polycyclic group comprising
from 8 to 60 carbon atoms and X is chosen from (i) the
groups OR0, R0 being a hydrocarbon residue comprising from
1 to 8 carbon atoms, optionally substituted by one or
more ester groups, and (ii) the groups deriving from
primary and/or secondary amines or from alkanolamines
with a linear or branched aliphatic hydrocarbon chain
comprising from 1 to 18 carbon atoms,
3) and from 5 to 20% by weight of at least one
glycerol diester of formulae (IIIA) and/or (IIIB) :

in which R3 and R4, which are identical or
different, are chosen from saturated or unsaturated,
linear or slightly branched, alkyl chains comprising from
8 to 24 carbon atoms, and cyclic and polycyclic groups
comprising from 8 to 60 carbon atoms.
Preference is given, among the glycerol mono-
esters of formula (I) and the diesters of formula (III)
with, respectively, Rx or R3 and R4 consisting of an alkyl
chain, to the monoesters and diesters obtained from the
oils of the group composed of lauryl oils originating
from copra or palm, which are rich in saturated alkyl
chains containing 12 to 14 carbon atoms, palmitic oils
resulting from palm, lard or tallow, containing a major
amount of saturated alkyl chains containing 16 carbon
atoms, linoleic oils resulting from sunflower, maize or
rape, containing a high content of linoleic acid,
linolenic oils from linseed, comprising significant
contents of triunsaturated alkyl chains containing from
1 to 18 carbon atoms, and ricinoleic oils resulting from
the castor oil plant.
Among the glycerol monoesters and diesters
obtained from polycyclic acids, the preferred monoesters
and diesters comprise an Rx or R3 and/or R4 composed of at
least two rings, each formed of 5 to 6 atoms, at most one
of which is optionally a heteroatom, such as nitrogen or
oxygen, and the others are carbon atoms, these two rings
additionally having two carbon atoms in common,
preferably vicinal, these said rings being saturated or
unsaturated. These are preferably glycerol monoesters of
natural resin acids obtained from the residues from the
distillation of natural oils extracted from resinous
trees, in particular resinous conifers.
Among these esters of resin acids according to
the invention, preference is given to esters of abietic
acid, of dihydroabietic acid, of tetrahydroabietic acid,
of dehydroabietic acid, of neoabietic acid, of pimaric
acid, of laevopimaric acid and of parastrinic acid.
By adjusting the operating conditions for partial
hydrolysis of these oils, it is possible directly to
obtain the mixture of glycerol monoalkyl esters/dialkyl
esters.
According to another form of the invention, it is
possible to prepare glycerol alkyl esters by an
esterification reaction between the carboxylic acids
described above and glycerol.
The esters and the amides of formula (II) can be
easily obtained by reaction of an alcohol, amine and/or
alkanolamine compound with an organic acid, such as oleic
acid, or a simple ester, such as methyl oleate, the
reaction being carried out under the conditions known per
se by a person skilled in the art for esterification and
amidation processes.
In a first embodiment, the alcohols used to
obtain the compound (II) are chosen from the group
composed of methanol, ethanol, propanol, isopropanol,
butanol, isobutanol, pentanol or 2-ethylhexanol, and/or
oxyalkylated alcohols of formula R(0-CH2-CHR')n-0H, in
which R is an alkyl group containing 1 to 6 carbon atoms,
R' is hydrogen or an alkyl group containing 1 to 4 carbon
atoms and n an integer varying from 1 to 5, such as
methyl cellosolve, butyl cellosolve, butyl digol and 1-
butoxypropanol.
In a second embodiment, the primary or secondary
amines used to obtain the compound (II) are chosen from
the group composed of methylamine, ethylamine, propyl-
amine, butylamine, isobutylamine, 2-ethylhexylamine,
decylamine, dodecylamine, stearylamine and oleylamine,
N,N-diethylamine, N,N-dipropylamine, N,N-dibutylamine,
N,N-di(2-ethylhexyl)amine, methyldecylamine, N-methyl-
dodecylamine and N-methyloleylamine.
In a third embodiment, for the compound (II), use
is made of alkanolamines chosen from amines containing 1
to 18 carbon atoms substituted by at least one hydroxy-
lated, hydroxymethylated, hydroxyethylated or hydroxy-
propylated group, such as ethanolamine, diethanolamine,
triethanolamine, isopropanolamine, diisopropanolamine,
triisopropanolamine, N-methylethanolamine, tris(hydroxy-
methyl)aminomethane, (N-hydroxyethyl)methylimidazoline or
(N-hydroxyethyl)heptadecenylimidazoline.
The additives obtained by physical mixing
according to the invention are used to improve the
lubricating power of diesel fuels for ground vehicle
engines, optionally as a mixture with at least one
oxygen-containing compound chosen from the group formed
by alcohols, ethers and esters, as well as with any
additive used to improve the quality of fuel, such as
detergent, dispersing, antioxidizing and antifoaming
additives or -even biofuel.
A second subject of the invention corresponds to
the fuels containing between 25 and 2500 ppm and pre-
ferably from 100 to 1000 ppm by weight of at least one
additive used according to the invention dispersed in a
diesel fuel which are defined by ASTM standard D-975.
The examples below are given by way of
illustration of the invention but do not limit the scope
thereof.
EXAMPLE I:
The object of the present example is to compare
the lubricating power of the lubricity additives
according to the invention with that of the known
lubricity additives with regard to wear under the HFRR
(High Frequency Reciprocating Rig) test conditions, as is
described by the standardized procedure CEC-F06-A96 in
the SAE 932692 article by J. W. Hadley of the University
of Liverpool.
The additives according to the invention will be
referenced Xi, while the comparative additives will be
referenced TA.
A first additive T1 is the product of the
reaction of oleic acid with diethanolamine. This reaction
is carried out in a 500 ml four-necked round-bottomed
flask into which are introduced first 84.6 g of oleic
acid and 105.3 g of xylene and then 31.5 g of diethanol-
amine over a period of 10 minutes. The entire mixture is
subsequently maintained under reflux in xylene for
6 hours in order to remove 6.4 ml of water. The final
product obtained contains 50% of active material with an
orangey-yellow colour. Analysis by infrared spectroscopy
exhibits absorption bands at 3500 cm"1, at 1730 cm"1 and at
1650 cm"1, corresponding respectively to the hydroxyl,
ester and amide functional groups.
The second additive T2 is the product of the
reaction of a tall-oil acid and of diethanolamine. The
tall-oil acid used is a combination of 70% of a mixture
of fatty acids (55% oleic acid, 38% linoleic acid, 5%
palmitic acid and 2% of linolenic acid) and of 30% of
resin acids exhibiting an acid number of 185 mg of KOH
per gram. The reaction is carried out as for T1 by
introducing 80 g of tall-oil acid, 28.2 g of diethanol-
amine and 98.6 g of xylene successively into the round-
bottomed flask and by maintaining reflux in xylene for
6 hours. The final reaction product is a clear, viscous,
orangey-yellow liquid having a residual acid number of
0.21 mg of KOH per gram.
The third additive T3 is a mixture of glycerol
alkyl esters, mono-, di- and trialkyl esters, mainly
comprising glycerol monooleate.
The first additive according to the invention X1
is a physical mixture of 2 g of the additive T2 and 1 g
of the additive T3.
The second additive according to the invention X2
is a physical mixture of 2 g of the additive T1 and 1 g
of the additive T3.
The additive T4 is the glycerol trioleate sold by
the company Fluka.
The third additive according to the invention X3
is the product of the reaction of gylcerol trioleate T4
with diethanolamine. The reaction is carried out in a
four-necked round-bottomed flask, as for Tx, by mixing
80 g of glycerol trioleate and 18.5 g of diethanolamine
and by then heating the entire mixture at 150°C for 4
hours.
The additive T5 is a soybean triglyceride oil
with an average molecular mass of approximately 870,
composed of 28% of oleic acid, 50% of linoleic acid, 8%
of linolenic acid, 3% of stearic acid, 10% of palmitic
acid and 1% of arachidic acid.
The fourth additive according to the invention X4
is the product of the reaction of 87 g of T4 with 21 g of
diethanolamine, the mixture being kept stirred at 150°C
for 6 hours. The additive X4 is a fluid, orangey-yellow
liquid exhibiting, by infrared spectrometry, the
absorption bands characteristic of the alcohol, ester and
amide functional groups.
The fifth additive according to the invention X5
is obtained under the same conditions as the additive X4
but by using 87 g of T4 and 15.75 g of diethanolamine.
The sixth additive according to the invention X6
is obtained under the same conditions as the additive X4
but by using 27 g of the additive Ts and 26 g of
diethanolamine.
The seventh additive according to the invention
X7 is obtained under the same conditions as the additive
X4 but by replacing diethanolamine by 24 g of tris-
(hydroxymethyl)aminomethane.
The eighth additive according to the invention X8
is obtained under the same conditions as the additive X4
but by using, as triglyceride, castor oil with an average
molecular mass of approximately 927 composed of 87% of
ricinoleic acid, 7% of oleic acid and 3% of stearic acid.
Each of the additives described above is
introduced into three different diesel oils A, B and C,
the characteristics of which are given in Table I below,
at a content of 100 ppm of active material.
The diesel oils A, B and C, thus treated with
additives, were subjected to the HFRR test, which
consists in jointly applying, to a steel ball in contact
with a motionless metal plate, a pressure corresponding
to a weight of 2 00 g and an alternating movement of 1 mm
at a frequency of 50 Hz. The moving ball is lubricated by
the test composition. The temperature is maintained at
6 0°C throughout the duration of the test, that is to say
75 min. The lubricating power is expressed by the mean
value of the diameters of the wear imprint of the ball on
the plate. A small wear diameter indicates a good
lubricating power; conversely, a large wear diameter
expresses a power which becomes increasingly insufficient
as the wear diameter increases.
It is found, from this Table II, that the
physical mixtures according to the invention, such as X1
and X2, have wear characteristics which are smaller and
thus clearly better than those of T1, T2 and T3, which
expresses the synergistic effect obtained by combination
of the predominant components of the lubricity additive
according to the invention. X3 corresponds to the
reaction product obtained according to the process of the
invention from diethanolamine with glycerol trioleate. As
above, the advantage of the additive thus obtained with
regard to the wear characteristics obtained with T4 is
perceived.
The performances of the additives X4, X5, X6 and
X7 are to be compared with those of the starting oil T5.
As above, the combination of the reaction products limits
the wear phenomena observed in the case of the oil alone.
CLAIMS
1. Use as lubricity additive for diesel and aviation
engine fuels, with a sulphur content of less than or
equal to 500 ppm, characterized in that the additive is
composed of:
¦ from 5 to 25% by weight of at least one
glycerol monoester of formulae (IA) and/or (IB) below:

with Rx chosen from saturated or unsaturated,
linear or slightly branched, alkyl chains comprising from
8 to 24 carbon atoms and cyclic and polycyclic groups
comprising from 8 to 60 carbon atoms,
¦ from 35 to 75% by weight of at least one
compound of formula (II) below;

in which R2 is a saturated or unsaturated, linear or
slightly branched, alkyl chain comprising from 8 to 24
carbon atoms, and X is chosen from (i) the groups OR0, R0
being a hydrocarbon residue comprising from 1 to 8 carbon
atoms, optionally substituted by one or more ester
groups, and (ii) the groups deriving from primary and/or
secondary amines or from alkanolamines with a linear or
branched aliphatic hydrocarbon chain comprising from 1 to
18 carbon atoms,
¦ from 0.1 to 20% by weight of at least one
glycerol diester of formula (IIIA) and/or (IIIB) :

in which R3 and R4 are identical or different and
are chosen from saturated or unsaturated, linear or
slightly branched, alkyl chains comprising from 8 to 24
carbon atoms and cyclic and polycyclic groups comprising
from 8 to 6 0 carbon atoms.
2. Use according to Claim 1, characterized in that
the glycerol monoesters of formula (I) and the diesters
of formula (III) with, respectively, Rx or R3 and R4
consisting of an alkyl chain are chosen from the
monoesters and diesters obtained from the oils of the
group composed of lauryl oils originating from copra or
palm, which are rich in saturated alkyl chains containing
12 to 14 carbon atoms, palmitic oils resulting from palm,
lard or tallow, containing a major amount of saturated
alkyl chains containing 16 carbon atoms, linoleic oils
resulting from sunflower, maize or rape, containing a
high content of linoleic acid, linolenic oils from
linseed, comprising significant contents of triun-
saturated alkyl chains containing 1 to 18 carbon atoms,
and ricinoleic oils resulting from the castor oil plant.
3. Use according to either of Claims 1 and 2,
characterized in that the gylcerol monoesters of formula
(I) and the glycerol diesters of formula (III) comprise
an Ri or R3 and/or R4 composed of at least two rings, each
formed of 5 to 6 atoms, at most one of which is
optionally a heteroatom, such as nitrogen or oxygen, and
the others are carbon atoms, these two rings additionally
having two carbon atoms in common, preferably vicinal,
these said rings being saturated or unsaturated.
4. Use according to Claim 3, characterized in that
the glycerol monoesters and diesters of formulae (I) and
(III) are obtained from natural resin acids contained in
the residues from the distillation of natural oils
extracted from resinous trees, in particular from
resinous conifers.
WE CLAIM:
1. A fuel composition with a sulphur content of less than or equal to 500
ppm, and comprising at least one additive, characterized in that the
additive is composed of:
from 5 to 25% by weight of at least one glycerol monoester of formulae
(Ia) and/or (Ib) below:

with R1 chosen from saturated or unsaturated, linear or slightly
branched, alkyl chains comprising from 8 to 24 carbon atoms and cyclic and
polycyclic groups comprising from 8 to 60 carbon atoms,
• from 35 to 75% by weight of at least one compound of formula (II)
below:

in which R2 is a saturated or unsaturated, linear or slightly branched,
alkyl chain comprising from 8 to 24 carbon atoms, and X is chosen from (i) the
groups OR0, R0 being a hydrocarbon residue comprising from 1 to 8 carbon
atoms, optionally substituted by one or more ester groups, and (ii) the groups
deriving from primary and/or secondary amines or from alkanolamines with a
linear or branched aliphatic hydrocarbon chain comprising from 1 to 18 carbon
atoms,
• from 0.1 to 20% by weight of at least one glycerol diester of formula
(IIA) and/or (IIIB):

in which R3 and R4 are identical or different and are chosen from
saturated or unsaturated, linear or slightly branched, alkyl chains comprising
from 8 to 24 carbon atoms and cyclic and polycyclic groups comprising from 8
to 60 carbon atoms.
2. Fuel composition as claimed in claim 1, wherein the glycerol monoesters
of formula (I) and the diesters of formula (III) with, respectively, R1 or R3
and R4 consisting of an alkyl chain are chosen from the monoesters and
diesters obtained from the oils of the group composed of lauryl oils
originating from copra or palm, which are rich in saturated alkyl chains
containing 12 to 14 carbon atoms, palmitic oils resulting from palm, lard
or tallow, containing a major amount of saturated alkyl chains
containing 16 carbon atoms, linoleic oils resulting from sunflower, maize
or rape, containing a high content of linoleic acid, linolenic oils from
linseed, comprising significant contents of triunsaturated alkyl chains
containing 1 to 18 carbon atoms, and ricinoleic oils resulting from the
castor oil plant.
3. Fuel composition as claimed in claims 1 and 2, wherein the glycerol
monoesters of formula (I) and the glycerol diesters of formula (III)
comprise an R1 or R3 and/or R4 composed of at least two rings, each
formed of 5 to 6 atoms, at most one of which is optionally a heteroatom,
such as nitrogen or oxygen, and the others are carbon atoms, these two
rings additionally having two carbon atoms in common, preferably vicinal
these said rings being saturated or unsaturated.

4. Fuel composition as claimed in claim 3, wherein the glycerol monoesters
and diesters of formulae (I) and (III) are obtained from natural resin acids
contained in the residues from the distillation of natural oils extracted
from resinous trees, in particular from resinous conifers.
5. Fuel composition as claimed in claim 4, wherein the esters of resin acids
are chosen from the group composed of esters of abietic acid, of
dihydroabietic acid, of tetrahydroabietic acid, of dehydroabietic acid, of
neoabietic acid, of pimaric acid, of laevopimaric acid and of parastrinic
acid.
6. Fuel composition as claimed in one of claims 1 to 5, wherein the esters
and the amides of formula (II) are obtained by reaction of an alcohol,
amine and/or alkanolamine compound with a carboxylic acid, such as
oleic acid, or alternatively methyl oleate.
7. Fuel composition as claimed in claim 6, wherein the alcohols are chosen
from alkanols of the group composed of methanol, ethanol, propanol,
isopropanol, butanol, isobutanol, pentanol or 2-ethylhexanol and/or
oxyalkylated alcohols of formula R(0-CH2-CHR')n-OH, in which R is an
alkyl group containing 1 to 6 carbon atoms, R' is hydrogen or an alkyl
group containing 1 to 4 carbon atoms and n an integer varying from 1 to
5, such as methyl cellosolve, butyl cello solve, butyl digol and I-
butoxypropanol.
8. Fuel composition as claimed in claim 6, wherein the amines are primary
and secondary amines chosen from the group composed of methylamine,
ethylamine, propylamine, butylamine, isobutylamine, 2-ethylhexylamine,
decylamine, dodecylamine, stearylamine and oleylamine, N,N-
diethylamine, N,N-dipropylamine, N,N-dibutylamine, N,N-di(2-
ethylhexyl)amine, N-methyldecylamine, N-methyldodecylamine or N-
methyloleylamine.
9. Fuel composition as claimed in claim 6, wherein the alkanolamines are
chosen from amines comprising from 1 to 18 carbons atoms substituted
by at least one hydroxylated, hydroxymethylated, hydroxyethylated or
hydroxypropylated group, such as ethanolamine, diethanolamine,
triethanolamine, isopropanolamine, diisopropanolamine,
triisopropanolamine, N-methylethanolamine, tris
(hydroxymethyl)aminomethane, (N-hydroxyethyl )methylimidazoline or (N
-hydroxyethyljheptadecenylimidazo line.
10. Fuel composition for ground vehicle engines as claimed in any one of
claims 1 to 9, wherein the fuel composition comprises 25 to 2500 ppm
and preferably from 100 to 1000 ppm by weight of at least one of said
additive, the said additive being introduced into a diesel fuel.

A fuel composition with a sulphur content of less than or equal to 500 ppm, and
comprising at least one additive, characterized in that the additive is composed of:
from 5 to 25% by weight of at least one glycerol monoester of formulae (IA) and/or (IB)
below:
with R1 chosen from saturated or unsaturated, linear or slightly branched, alkyl
chains comprising from 8 to 24 carbon atoms and cyclic and polycyclic groups
comprising from 8 to 60 carbon atoms,
• from 35 to 75% by weight of at least one compound of formula (II) below:
in which R2 is a saturated or unsaturated, linear or slightly branched, alkyl
chain comprising from 8 to 24 carbon atoms, and X is chosen from (i) the groups ORo,
Ro being a hydrocarbon residue comprising from 1 to 8 carbon atoms, optionally
substituted by one or more ester groups, and (ii) the groups deriving from primary
and/or secondary amines or from alkanolamines with a linear or branched aliphatic
hydrocarbon chain comprising from 1 to 18 carbon atoms,
• from 0.1 to 20% by weight of at least one glycerol diester of formula (IIIA)
and/or (IIIB):
in which R3 and R4 are identical or different and are chosen from saturated or
unsaturated, linear or slightly branched, alkyl chains comprising from 8 to 24 carbon
atoms and cyclic and polycyclic groups comprising from 8 to 60 carbon atoms.

Documents:

in-pct-1999-22-kol-abstract.pdf

in-pct-1999-22-kol-claims.pdf

in-pct-1999-22-kol-correspondence 1.1.pdf

in-pct-1999-22-kol-correspondence.pdf

in-pct-1999-22-kol-description (complete).pdf

in-pct-1999-22-kol-examination report 1.1.pdf

in-pct-1999-22-kol-examination report.pdf

in-pct-1999-22-kol-form 1.pdf

in-pct-1999-22-kol-form 13.1.pdf

in-pct-1999-22-kol-form 13.pdf

in-pct-1999-22-kol-form 18.1.pdf

in-pct-1999-22-kol-form 18.pdf

in-pct-1999-22-kol-form 2.1.pdf

in-pct-1999-22-kol-form 2.pdf

in-pct-1999-22-kol-form 3.1.pdf

in-pct-1999-22-kol-form 3.pdf

in-pct-1999-22-kol-form 5.1.pdf

in-pct-1999-22-kol-granted-abstract 1.1.pdf

in-pct-1999-22-kol-granted-claims 1.1.pdf

in-pct-1999-22-kol-granted-description (complete) 1.1.pdf

in-pct-1999-22-kol-granted-form 1.1.pdf

in-pct-1999-22-kol-granted-form 2.1.pdf

in-pct-1999-22-kol-granted-specification 1.1.pdf

in-pct-1999-22-kol-others.pdf

in-pct-1999-22-kol-pa 1.1.pdf

in-pct-1999-22-kol-pa.pdf

in-pct-1999-22-kol-priority document.pdf

in-pct-1999-22-kol-reply to examination report 1.1.pdf

in-pct-1999-22-kol-reply to examination report.pdf

in-pct-1999-22-kol-specification.pdf

in-pct-1999-22-kol-specification1.1.pdf

in-pct-1999-22-kol-translated copy of priority document 1.1.pdf

in-pct-1999-22-kol-translated copy of priority document.pdf


Patent Number 244070
Indian Patent Application Number IN/PCT/1999/22/KOL
PG Journal Number 47/2010
Publication Date 19-Nov-2010
Grant Date 16-Nov-2010
Date of Filing 30-Aug-1999
Name of Patentee ELF ANTAR FRANCE
Applicant Address TOUR ELF-2 PLACE DE KA COUPOLE, LA DEFENSE 6, F-92400 COURBEVOIE
Inventors:
# Inventor's Name Inventor's Address
1 MALDONADO PAUL 23 AVENUE DU 8 MAI 1945, F-69360 SAIN SYMPHORIEN D'OZON
2 EBER DANIELE 15 RUE DES NOYERS, F69005 LYON
3 GERMANAUD LAURENT ROUTE DE LAFAYETTE, VALENCIN LE FAYET, F-38540 HEYRAUX
PCT International Classification Number C10L 1/18
PCT International Application Number PCT/FR1998/02823
PCT International Filing date 1998-12-22
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 97 16538 1997-12-24 France
2 98 03225 1998-03-17 France