Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2002-07-23
2004-02-10
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S133000, C516S131000, C510S264000, C508S194000, C252S392000
Reexamination Certificate
active
06689908
ABSTRACT:
This application is a G 371 of PCT/FR00/02502, field Sep. 11, 2000.
The present invention relates to polyalkoxylated superamides, which may be functionalised. More particularly, it relates to superamides comprising a block derived from propylene oxide then a block derived from ethylene oxide.
The present invention also relates to their use as an emulsifying agent, preferably for oils.
It also relates to the use of such compounds as a lubricating agent or as an anti-corrosion agent.
The term “superamides” means the family of alkanolamides obtained by transamidification of a fatty acid ester.
Alkanolarnides exist that are obtained by amidification of a fatty acid. However, they are obtained in the form of a mixture comprising the amide, amine, fatty acid and water. Typically, the amide concentration is 60-65%.
In contrast, in the case of superamides, the final mixture contains more than 90% of superamides, constituting a clear advantage. During synthesis of the superamide, the alcohol from the fatty acid used is distilled off during the reaction, taking that reaction to completion.
The superamides of the invention correspond to the following formulae (I) and/or (II):
[R
1
—CONR
2
—CH
2
CHR
3
—O—(CHR
4
—CHR
5
O)
m
—(CH
2
CH
2
O)
n
]
p
—X (I)
R
1
—CON—[CH
2
CHR
3
—O—(CHR
4
—CHR
5
O)
m
—(CH
2
CH
2
O)
n
—X]
2
(II)
in which formulae:
R
1
represents a linear or branched, saturated or unsaturated C
7
-C
22
hydrocarbon radical, which optionally carries at least one hydroxyl group;
R
2
represents a hydrogen atom or a C
1
-C
4
hydrocarbon radical;
R
3
represents a hydrogen atom or a C
1
-C
4
hydrocarbon radical;
R
4
and R
5
, which may or may not be identical, represent a hydrogen atom or an alkyl radical containing 1 or 2 carbon atoms, provided that at most one of these two radicals is a hydrogen atom;
X represents a hydrogen atom, a C
1
-C
6
hydrocarbon radical, or a phosphate, carboxylate, sulphate or sulphonate group;
m is an average number in the range 0 (excluded) to 20;
n is an average number in the range 0 (excluded) to 50;
p is 1 or 2, depending on the nature of X.
More particularly, radical R
1
is a linear or branched, saturated or unsaturated C
10
-C
22
hydrocarbon radical, optionally carrying at least one hydroxyl group. Preferably, said radical comprises at least one ethylenically unsaturated bond.
More precisely, radical R
1
derives from fatty acids or oils of animal or plant origin.
Examples of C
10
-C
22
saturated fatty acids that can be cited include lauric acid, capric acid, decanoic acid, stearic acid, isostearic acid, gadoleic acid, myristic acid and mixtures thereof
Non limiting examples of C
10
-C
22
fatty acids carrying at least one ethylenically unsaturated bond that can be cited are linderic acid, myristoleic acid, palmitoleic acid, oleic acid, petroselenic acid, doeglic acid, erucic acid, linoleic acid, linolenic acid, isanic acid, stearodonic acid, arachidonic acid, chypanodonic acid, ricinoleic acid and mixtures thereof.
Of the above acids, radical R
1
more particularly derives from fatty acids selected from palmitoleic acid, oleic acid, petroselenic acid, erucic acid, linoleic acid, linolenic acid, ricinoleic acid and mixtures thereof.
Oils from which radical R
1
derives that can be cited include oils of animal or plant origin.
Suitable animal oils that can be cited include sperm whale oil, dolphin oil, whale oil, seal oil, sardine oil, herring oil, dogfish oil, cod liver oil; calves' foot oil and beef, pork, horse or sheep fat (tallow).
Examples of oils of plant origin that can be mentioned include rapeseed oil, sunflower seed oil, peanut oil, olive oil, walnut oil, corn oil, soya oil, linseed oil, hemp oil, grapeseed oil, coprah oil, palm oil, cottonseed oil, babassu oil, jojoba oil, sesame seed oil, castor oil and coriander oil. Preferably, rapeseed oil is used.
Finally, R
1
can derive from products resulting from alcoholysis reactions, more precisely methanolysis of the above oils.
Radicals R
2
and R
3
, which may or may not be identical, represent a hydrogen atom or a C
l
-C
4
hydrocarbon radical, which is more particularly saturated. Preferably, radicals R
2
and R
3
represent a hydrogen atom, or a methyl radical, an ethyl radical, a propyl radical or its isomers, or a butyl radical or its isomers.
More preferably, radicals R
4
and R
5
are selected from hydrogen or the methyl radical, provided that at least one of the two radicals but not both at the same time represents a hydrogen atom. In this preferred embodiment, this motif derives from propylene oxide.
The coefficient m, representing an average number, is in the range 0 (excluded) to 20. Preferably, this coefficient is in the range 0 (excluded) to 10.
The coefficient n, representing an average number, is in the range 1 to 50, more particularly in the range 1 to 20.
The compounds of the present invention can be in the non ionic or ionic form.
In the first possibility, radical X represents a hydrogen atom or a C
1
-C
6
hydrocarbon radical. In such a case, the value of coefficient p is 1.
In the second possibility, the superamides are in an ionic form.
A first variation of this possibility corresponds to compounds in which X represents a phosphate function. In this first variation, we can envisage superamides in which the coefficient p is 1 (phosphate monoester) or p is 2 (phosphate diester). More precisely, in the case of formula (I), the phosphated superamide corresponds to the following formula:
[A]
p
—P(═O)(OM)
p
In this formula:
A represents R
1
—CONR
2
—CH
2
CHR
3
O—(CHR
4
—CHR
5
O)
m
—(CH
2
CH
2
O)
n
—
R
1
, R
2
, R
3
, R
4
, R
5
, m and n being as defined above;
M represents a hydrogen atom, an alkali or alkaline-earth metal, an ammonium residue with formula N(R)
4
+
where R, which may or may not be identical, corresponds to a hydrogen atom, a saturated or unsaturated, linear, branched or cyclic C
1
-C
22
hydrocarbon radical, preferably C
1
-C
6
, optionally carrying at least one hydroxyl group;
p corresponds to 1 or 2, p′ to 2 or 1, and p+p′=3.
A second variation of this possibility corresponds to compounds for which X represents a carboxylate function with formula —(CH
2
)
r
—COOM, in which:
M has the definition given above;
r equals 1 or 2.
In a third variation, the compound of the invention comprises a radical X defined by the following formula: —SO
3
M, in which M is as defined above.
In a fourth variation, the compounds of the invention comprise a radical X defined by the following formula: —(CH
2
)
s
—SO
3
M, in which formula M has the meanings given above, and s is equal to 2 or 3.
It should be noted that the superamides of the invention could be present alone or as a mixture.
The process for preparing the superamides described above consists of carrying out the following steps:
a) firstly, reacting a fatty acid ester the acid-derived portion of which is a linear or branched, saturated or unsaturated C
7
-C
22
hydrocarbon radical that may carry at least one hydroxyl group; and in which the alcohol-derived portion is a C
1
-C
4
hydrocarbon radical, with an alkanolamine with formula NH
1
R
2
—CH
2
—CHR
3
—OH or NH—(CH
2
—CHR
3
—OH)
2
, optionally in the presence of a basic compound;
b) reacting the product obtained at the end of step a) with a compound with formula:
where R
4
and R
5
are as defined above
c) reacting the product obtained at the end of step b) with ethylene oxide;
d) optionally, carrying out a step for functionalising the product obtained during step
c) with the aim of replacing the terminal hydrogen atom with a hydrocarbon radical, a phosphate function, a carboxylate function, a sulphate function or a sulphonate function;
the proportions of the various reactants employed being such that formulae (I) or (II) are satisfied
Step a) is carried out in the presence of a fatty acid ester or a mixture of such esters. The fatty acids described in the definition of radical R
1
can be carried out and the list will not be repeated here. Regarding the alcohol porti
Joye Jean-Lue
Le Helloco Jean-Guy
Taverna Cristiano Carlo
Kumar Shailendra
Rhodia Chimie
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