Condensates

Details Condensates Condensates

2000-12-11

2002-06-04

McAvoy, Ellen M. (Department: 1764)

Solid anti-friction devices, materials therefor, lubricant or se

Lubricants or separants for moving solid surfaces and...

Organic -co- compound

C508S502000, C508S510000, C562S468000, C562S476000, C562S477000, C562S044000, C562S830000, C562S403000

Reexamination Certificate

active

06399549

ABSTRACT:

The present invention relates to condensates in particular cyclic calixarene compounds which are cyclic phenolic compounds. The compounds of the invention are particularly suitable as thermal stabilising additives in fuel and for use in lubricating oil compositions for medium or low speed diesel engines, especially four stroke engines. The invention also relates to fuel compositions and to lubricating oil compositions comprising said compounds, e.g. aviation fuel compositions.
In high speed aircraft, both civilian and military, the liquid fuel is combusted to produce power, but also is circulated in the aircraft as a heat exchange fluid to remove the excess heat generated at such speeds e.g. in lubricating oils. The fuel is thus maintained for long periods at high temperatures, which results in discoloration and decomposition to produce soluble coloured products and insoluble products such as gums, sediments and granular material; insoluble products can form deposits that reduce the heat exchange capacity and can block filters potentially causing loss of power. Soluble coloured by-products are unsightly and an indication of some decomposition. The cause of discoloration etc. may be from phenols, naphthenates and sulphur compounds and/or metals which are often present in the fuels.
In some oil fired devices, such as boilers and slow heating cookers, e.g. of the Aga type, kerosine oil fuel is passed down a narrow metal feed pipe to the combustion chamber where it is burnt. Parts of the pipe are sufficiently near the hot chamber for them to be heated to significant temperatures, resulting in the risk of thermal degradation of the fuel in the pipe, especially with slow feed rates and high residence times in the pipe. This degradation can form solid deposits which reduce the flow and ultimately stop it, causing the combustion to stop. To overcome this manufacturers of such devices have for many years recommended to their users that at least once each 6 months such pipe parts are cleaned of solid deposits of coke or other materials.
U.S. Pat. No. 5,478,367 describes the addition to diesel or jet fuel of a substituted unsaturated polyamine derivative dispersant to reduce particulate emissions on combustion and to reduce fouling i.e. deposition of insoluble deposits. The macrocyclic compounds preferably contain an N═C—N—C═O group and especially have fused rings, such as are made by reaction of a hydrocarbyl (e.g. fatty alkyl) succinic anhydride and a polyalkylene amine.
Canadian Patent Publ. 2067907 describes the addition to distillate jet fuels of hydroxylamines to stabilise them against degradation at elevated temperatures.
U.S. Pat. No. 5,468,262 describes addition to jet fuels of thermal stability additives which are prepared by reacting a polyamine, aldehyde and phenol to form a condensate which is then reacted with a succinic anhydride containing a polyolefin derived unsaturated group.
The additives are effective at 0.2% by weight.
EP-A-678568 describes addition to jet engine fuels of anti deposition agents which are derivatives of (thio)phosphonic acids.
Accordingly the present invention provides a cyclic compound comprising m units of the formula Ia.
and n units of the formula (Ib)
joined together to form a ring, wherein Y and Y
2
are divalent bridging groups which may be the same or different in each unit; R
o
is H or (C
1
-C
6
) alkyl or is a metal or ammonium cation, (so the group CO
2
R
0
is a carboxylic salt); R
5
is H or (C
1
-C
60
) alkyl or OH group; and j is 1 or 2; R
3
is hydrogen, a hydrocarbyl or a hetero-substituted hydrocarbyl group; each of R
1
, R
2
and R
4
, which may be the same or different, is hydroxyl, hydrogen, hydrocarbyl or hetero-substituted hydrocarbyl, with the proviso that at least one of R
1
, R
2
, R
4
is hydroxyl, and m+n is 4 to 20, m is 1-8 and n is at least 3 and preferably either R
1
is hydroxyl and R
2
and R
4
are independently either hydrogen, hydrocarbyl or hetero-substituted hydrocarbyl, or R
2
and R
4
are hydroxyl and R
1
is either hydrogen, hydrocarbyl or hetero-substituted hydrocarbyl; and m+n is from 4 to 20, m is from 1 to 8 and n is at least 3, with the proviso that in formula Ia at least one OH group is in the meta or para position to the COOR
o
group and/or at least one R
5
group is OH. Preferably in a second proviso, at least one of the following features (a) to (e) is met, namely the cyclic compound comprises at least one of (a) at least one formula (Ia) unit in the form of a carboxylate anion especially at least 2 carboxylate anions (b) at least one formula (Ia) unit in the form of an alkaline earth metal or alkali metal carboxylate salt, preferably a potassium or sodium salt, especially a potassium salt (c) at least 2 e.g. 3 or 4 units of formula (Ia) (d) an m+n value of 5-11, preferably 7-9 and especially 8 and (e) the cyclic compound is in the substantial absence of linear species comprising formula (Ia) and (Ib) units and/or or the substantial absence of unreacted formula (Ia) and (Ib) units, (e.g. of formula IIa and IIb hereafter).
Preferably the cyclic compound has at least 2 of (a) (b) (c) (d) and (e) preferably 3, most preferably 4 and especially all 5 in particular (a) and (c), or (b) and (c), and especially (d). In a preferred embodiment the invention provides a cyclic compound wherein m is 2, n is 6, and both the units of formula (Ia) are in the form of a potassium carboxylate salt, and the cyclic compound is in the substantial absence of linear species comprising formula (Ia) and (Ib) units and the substantial absence of unreacted formula (Ia) and (Ib) units.
When more than one —CO
2
R
0
containing aromatic group unit is present in the ring (i.e. m>1), the phenol units and the —CO
2
R
o
containing aromatic groups may be distributed randomly, although this does not exclude the possibility that in some rings there may be several —CO
2
R
o
containing aromatic groups joined together in a row. Thus the m and n units may be joined in block and/or randomly.
If desired, in addition to containing at least one unit of formula Ia, the cyclic compound may also contain at least one unit of formula
where R
15
is H or C
1-60
alkyl, and R
16
and Y
3
are as described above for R
0
and Y
2
respectively. Preferred groups for R
15
, R
16
and Y
3
are as described below for R
5
, R
0
and Y/Y
2
(apart from OH for R
5
). The preferred unit is derived from salicylic acid. The cyclic compound may contain 1-4 units of formula Ia and 1-4 units of formula Id, especially 1 or 2 of formula Ia and 1 or 2 of formula Id, in particular with a total of both of 2 or 3, preferably the cyclic compound consists essentially of units of formula 1a and 1b.
In the formulae Ia/Ib Y, and Y
2
may each independently be a hydrocarbyl bridging group or be a hetero-substituted hydrocarbyl group or up to 50% mole of the totality of Y, and Y
2
group may be a hetero atom. The hydrocarbyl bridging group is preferably aliphatic and has a chain of 1-4 carbon atoms; preferably the group is of formula (CR
7
R
8
)
d
e.g. (CHR
8
)
d
where each of R
7
and R
8
, which may be the same or different, represents hydrogen or hydrocarbyl e.g. of 1-20 carbons such as 1-6 carbons or 6-20 carbons, such as methyl or ethyl and d is an integer of 1-4 preferably 2 or especially 1; advantageously the group is of formula (CHR
8
)
d
where R
8
is as defined above preferably methyl or especially hydrogen. Y, and/or Y
2
may also represent a hetero-substituted hydrocarbyl group with a hetero atom, e.g. O, S or NH interrupting a chain of carbon atoms e,g. 2-4 carbon atoms, such as in CH
2
OCH
2
, CH
2
SCH
2
or CH
2
NHCH
2
. Up to 50 mole % of the totality of Y and Y
2
groups may be a hetero atom e.g. O or NH or especially 5, e.g. 1-50 mole % especially 8-20 mole % of said groups. Preferably Y and Y
2
are hydrocarbyl groups, and the compound of formula I is sulphur free.
In the group of formula Ia, the group Y is usually ortho or para to an OH group and/or is usually meta to the CO
2
R
o
, but can be ortho to said CO
2
R
o
group

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