Fuel and related compositions – Liquid fuels – Containing organic -c
Reexamination Certificate
2000-08-18
2002-10-01
Medley, Margaret (Department: 1714)
Fuel and related compositions
Liquid fuels
Containing organic -c
C044S391000
Reexamination Certificate
active
06458173
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to a fuel additive and fuel composition containing the same. More in particular, the invention relates to a fuel additive acting as a detergent and as a lubricity additive in fuel compositions, in particular in low-sulphur fuel compositions, more in particular in low-sulphur diesel fuel compositions.
BACKGROUND OF THE INVENTION
From EP-A-0,798,364 fuel additives are known, based on either the salt of a carboxylic acid and an aliphatic amine, or an amide obtained by dehydration-condensation between a carboxylic acid and an aliphatic amine. The additive can be incorporated into a fuel, i.e., a diesel fuel, and thus reduce the amount of deposit in the injection nozzle of a compression-ignition diesel engine, improve lubricity of the diesel fuel, and reduce wear of the fuel injection pump of the engine. In short, the additive acts as a detergent and as a lubricity additive. Fuel additives acting both as detergent and as lubricity additive are rare. It would therefore be desirable to extend the range of such additives, or better still, to provide improved additives acting both as detergent and lubricity additive.
SUMMARY OF THE INVENTION
Accordingly, the invention provides the use of a poly(hydroxycarboxylic acid)amide or -ester derivative of general formula I:
wherein R is the residue of an amine, an aminoalcohol or a polyol linked to the or each poly(hydroxycarboxylic acid) via an amide or ester linkage; R
1
is hydrogen or optionally substituted hydrocarbyl group containing up to 50 carbon atoms; A is an optionally substituted hydrocarbyl group; n is from 1-100, preferably 1-10 and p is from 1-5, as a fuel additive acting as a detergent and as a lubricity additive in fuel compositions.
Moreover, the invention provides a fuel oil composition comprising of a major amount of a fuel oil, and a minor amount of an the additive as well as a additive concentration for use in a fuel oil composition.
DETAILED DESCRIPTION OF THE INVENTION
As used herein, the term “hydrocarbyl” represents a radical formed by removal of one or more hydrogen atoms from a carbon atom of a hydrocarbon (not necessarily the same carbon atoms in case more hydrogen atoms are removed). In case of R
1
useful hydrocarbyls are aromatic, aliphatic, acyclic or cyclic. Preferably, the hydrocarbyls are aryl, cycloalkyl, alkyl or alkenyl, in which case they may be straight-chain or branched-chain. Representative hydrocarbyls include phenyl, naphthyl, methyl, ethyl, butyl, pentyl, methylpentyl, hexenyl, dimethylhexyl, octenyl, cyclooctenyl, methylcyclooctenyl, dimethylcyclooctyl, ethylhexyl, octyl, isooctyl, dodecyl, hexadecenyl, eicosyl, hexacosyl, triacontyl and phenylethyl. The optionally substituted R
1
is preferably aryl, alkyl or alkenyl containing up to 50 carbon atoms, especially from 7 to 25 carbon atoms such as heptyl, octyl, undecyl, lauryl, heptadecyl, heptadenyl, heptadecadienyl, stearyl, oleyl, or linoleyl. Other examples of R
1
include C
4-8
cycloalkyl such as cyclohexyl; polycycloalkyls such as polycyclic terpenyl groups which are derived from naturally occurring acids such as abietic acid; aryl such as phenyl; aralkyl such as benzyl; polyaryl such as naphthyl, biphenyl, stibenyl and phenylmethylphenyl.
When the hydrocarbyl is substituted, it may contain a functional group such as carbonyl, carboxyl, nitro, hydroxy, halo, alkoxy, tertiary amino (no N—H linkages), oxy, cyano, sulfonyl and sulfoxyl. The majority of the atoms, other than hydrogen, in substituted hydrocarbyls are carbon, with the heteroatoms (e.g., oxygen, nitrogen and sulphur) representing only a minority, about 33% or less, of the total non-hydrogen atoms present.
Those skilled in the art will appreciate that functional groups such as hydroxy, halo, alkoxy, nitro and cyano in a substituted hydrocarbyl group will displace one of the hydrogen atoms of the hydrocarbyl, whilst functional groups such as carbonyl, carboxyl, tertiary amino (—N—), oxy, sulfonyl and sulfoxyl in a substituted hydrocarbyl group will displace a —CH— or —CH
2
— moiety of the hydrocarbyl.
In “optionally substituted hydrocarbyl of 1 to 50 carbon atoms”, the expression “1 to 50 carbon atoms” represents the total number of carbon atoms in the optionally substituted hydrocarbyl group. The same applies to “optionally substituted hydrocarbyl” of lower numbers of specified carbon atoms.
The or each radical R
1
is preferably unsubstituted or subtituted by a group selected from hydroxy, halo or alkoxy group, especially C
1-4
alkoxy. Preferred R
1
are residues of a stearyl, oleyl, 12-hydroxystearyl, 12-hydroxyoleyl, and that derived from naturally occurring oil such as tall oil fatty acid.
The moiety represented by A may be an aromatic, aliphatic or cycloaliphatic group. It is preferably an arylene, alkylene or alkenylene group, especially one containing from 4 to 25 carbon atoms with at least 4 carbon atoms between the oxygen atom and carbonyl group. More preferably it is a saturated alkylene group or an arylene group. When n is greater than 1, this moiety may be the same or different. This moiety may carry other substituents which do not confer water solubility on the molecule, such as halogen and C
1-4
alkoxy. Preferred examples of O—A—CO— are 12-oxystearyl, 12-oxyoleyl and 6-oxycaproyl. More preferred examples are saturated groups such as 12-oxystearyl, 6-oxycaproyl.
The amines, aminoalcohols or polyols which react with poly(hydroxycarboxylic acid) to form products of formula I are as defined in WO97/41092. For example, various amines and their preparations are described in U.S. Pat. Nos. 3,275,554, 3,438,757, 3,454,555, 3,565,804, 3,755,433 and 3,822,209. Complex amines such as “Starburst” (Trade Mark) dendrimers may be used, e.g. the compound of formula [CH
2
N((CH
2
)
2
CONH (CH
2
)
2
NH
2
)
2
]
2
.
Examples of polyols include ethylene glycol, glycerol, trimethylolethane, trimethylolpropane, 1,2-butanediol, 2,3-hexanediol, 2,4-hexanediol, pinacol, erythritol, arabitol, sorbitol, mannitol, pentaerythritol, dipentaerythritol and tripentaerythritol. Preferred derivatives of formula I are those wherein the compound of R(H)p, of which R represents the residue, has the general formula II:
HX[(CR
2
R
2
)
a
O]
b
[(CR
3
R
3
)
c
NR
4
]
d
[R
9
)
s
(CHR
3
)
e
R
5
]
f
[(CR
3
R
3
)
g
(R
6
)
h
]
i
R
7
(II)
wherein X is O or NR
4
; each R
2
independently represents hydrogen, hydrocarbyl of 1 to 10 carbon atoms or hydrocarbyl of 1 to 10 carbon atoms substituted by at least one hydroxy group; each R
3
independently represents hydrogen or hydrocarbyl of 1 to 10 carbon atoms; each R
4
independently represents hydrogen or hydrocarbyl of 1 to 10 carbon atoms; R
5
represents a C
5-7
cycloalkanediyl —NH— or 1,4-piperazinediyl moiety optionally substituted by one or more hydrocarbyl groups of 1 to 10 carbon atoms; each R
6
independently represents NR
8
or CHR
8
; R
7
represents hydrogen, hydrocarbyl of 1 to 30 carbon atoms or a —CO (CHOH)
t
(CR
3
R
3
)
j
(NR
3
)
k
(CR
3
R
3
)
1
OH group; R
8
represents a —(CR
3
R
3
)
r
NR
4
R
7
group; R
9
represents a C
5-7
cycloalkanediyl moiety optionally substituted by one or more hydrocarbyl groups of 1 to 10 carbon atoms; a is 1 to 10; b is 0 to 10; c is 1 to 10; d is 0 to 10; e is 1 to 10; f is 0 or 1; g is 1 to 10; h is 0 or 1; i is 0 to 10; j is 1 to 10; k is 0 or 1; 1 is 1 to 10; r is 1 to 10; s is 0 or 1, and t is 0 or 1; and integers b, d, f and i indicate numbers of associated moieties present, and the various moieties [(CR
2
R
2
)
a
O], [(CR
3
R
3
)
c
NR
4
], [(CHR
3
)
e
R
5
] and [(CR
3
R
3
)
g
(R
6
)
h
] may be in any linear order.
Preferably in formula II X is O or NR
4
, each R
2
independently represents hydrogen, C
1-4
alkyl or C
1-4
hydroxyalkyl, each R
3
independently represents hydrogen or C
1-4
alkyl, each R
4
represents hydrogen or methyl, R
5
represents a 1,4-piperazinediyl moiety or a cyclohexanediyl —NH— moiety optionally substituted by up to three methyl groups, each R
6
Infineum International Ltd.
Medley Margaret
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