Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Heterocyclic ring compound; a heterocyclic ring is one...
Reexamination Certificate
1999-11-02
2001-09-04
Johnson, Jerry D. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Heterocyclic ring compound; a heterocyclic ring is one...
C544S196000, C544S198000
Reexamination Certificate
active
06284717
ABSTRACT:
The present invention relates to triazine derivatives, a process for their preparation, lubricating oil compositions, fuel compositions and additive concentrates containing them and their use as dispersant additives.
In accordance with the present invention there is provided the reaction product of:
(i) a polyalkenyl derivative of an ethylenically unsaturated carboxylic reagent and
(ii) a compound of the formula
wherein R is a linear alkylene group having at least 2 carbon atoms, a branched alkylene group having at least 3 carbon atoms, a cycloalkylene group having at least 5 carbon atoms, in which one or more of said carbon atoms may be substituted by one or more hetero atoms, or is an aromatic group or a group of the formula
in which a is 1 to 6 and b is 0 to 6, wherein the groups R may be the same or different, and wherein the values of a and b may be the same or different.
The ethylenically unsaturated carboxylic reagent contains a total of at least 3 carbon atoms, preferably a total of from 3 to 50, more preferably from 3 to 30, still more preferably from 4 to 20, and even more preferably from 4 to 10, carbon atoms.
The ethylenically unsaturated carboxylic reagent may be an alpha-beta olefinic unsaturated carboxylic reagent as described at page 6, lines 15 to 48 of EP-B-0285609 or page 6, lines 11 to 39 of EP-B-0287569, e.g. acrylic acid (C
3
), methacrylic acid (C
4
), cinnamic acid (C
9
), crotonic acid (C
4
), 2-phenylpropenoic acid (C
9
), maleic acid (C
4
), fumaric acid (C
4
), glutaconic acid (C
5
), mesaconic acid (C
5
), itaconic acid (methylene succinic acid) (C
5
), citraconic acid (methyl maleic acid) (C
5
) and functional derivatives thereof such as anhydrides (e.g. maleic anhydride (C
4
), glutaconic anhydride (C
5
), itaconic anhydride (C
5
), citraconic anhydride (C
5
)), esters (e.g. methyl acrylate (C
4
)), amides, imides, salts, acyl halides and nitriles.
Preferably the ethylenically unsaturated carboxylic reagent is selected from monoethylenically unsaturated C
4
-C
10
dicarboxylic acids and anhydrides, of which maleic anhydride is most preferred.
The polyalkenyl derivative of an ethylenically unsaturated carboxylic reagent may be prepared by methods known in the art. For example, if the ethylenically unsaturated carboxylic reagent is maleic anhydride, the polyalkenyl derivative thereof may conveniently be prepared by mixing a polyalkene with a specified amount of maleic anhydride and passing chlorine through the mixture, e.g. as described in GB-A-949981. Alternatively, the derivative may be prepared by reacting thermally, at an appropriate temperature, the polyalkene with a specified amount of maleic anhydride, e.g. as described in GB-A-1483729. In EP-A-0542380 is described a process for preparing such a derivative, which involves reacting the polyalkene with maleic anhydride in a mol ratio of maleic anhydride to polyalkene of greater than 1:1, at a temperature in the range from 150 to 260° C. and in the presence of a polyaddition-inhibiting amount of a sulphonic acid. The molar ratio of ethylenically unsaturated carboxylic moiety to polyalkenyl moiety in the derivative formed is preferably 1:1 to 5:1, more preferably 1:1 to 3.5:1, particularly 1.5:1 to 2:1.
The polyalkene used to prepare the polyalkene derivative may be a homopolymer or copolymer, for example of at least one C
2-10
monoolefin. Preferably the polyalkene is a polymer of at least one C
2-5
monoolefin, e.g. an ethylene-propylene copolymer. The monoolefin is preferably a C
3-4
olefin, in particular propylene or isobutylene, and preferred polyalkenes derived therefrom include polyisobutylenes and atactic or isotactic or syndiotactic propylene oligomers. Polyisobutylenes such as that sold by BASF under the trade mark “GLISSOPAL” and those sold by the British Petroleum Company under the trade marks “ULTRAVIS” (both having high levels (about 80 to 90%) of terminal vinylidene unsaturation), “HYVIS” and “NAPVIS”, e.g. “HYVIS 75”, “HYVIS 120”, “HYVIS 200”, “NAPVIS 10” and “NAPVIS 120” polyisobutylenes, are especially preferred for use in the present invention.
The polyalkene has a number average molecular weight (M
n
) preferably in the range from 300 to 7000, more preferably from 500 to 5000, still more preferably from 700 to 3000.
Compounds of the formula of reactant (ii) and their preparation are described in EP-B-0240867. In said compounds, when R is a linear alkylene group it preferably contains 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly 2 to 12 carbon atoms, especially ethylene, propylene, butylene, pentylene and hexylene groups. When R is a branched alkylene group, it preferably contains 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, particularly where the branches comprise low alkyl groups such as methyl, ethyl and propyl. When R is a cycloalkylene group, it is preferably a 1,2-cyclohexyl, 1,3-cyclohexyl or 1,4-cyclohexyl group. One or more, preferably 2 or 3, of the carbon atoms in said groups R may be substituted by heteroatoms selected from oxygen and sulphur atoms, or nitrogen atoms in the form of the group —NHR′—, wherein R′ can be various moieties, in particular an alkyl group, more preferably containing 1 to 6 carbon atoms, or a hydrogen atom. When R is an aromatic group, it is preferably a phenylene or naphthylene group, particularly an ortho-, meta- on para-phenylene group. Such an aromatic group may be substituted, for example by one or more halogen atoms, alkyl groups, alkoxy groups, hydroxyl groups and equivalent groups. When R is a group of the formula
it is optionally substituted in the core or the side-chains by substituents referred to above in relation to the aromatic groups. Compounds of particular interest include tris-(6-aminohexyl)-melamine (i.e. each group of R is hexylene) (“TAHM”).
The present invention further provides a process for the preparation of a reaction product as defined above which comprises reacting
(i) a polyalkenyl derivative of an ethylenically unsaturated carboxylic reagent and
(ii) a compound of the formula
wherein R is a linear alkylene group having at least 2 carbon atoms, a branched alkylene group having at least 3 carbon atoms, a cycloalkylene group having at least 5 carbon atoms, in which one or more of said carbon atoms may be substituted by one or more hetero atoms, or is an aromatic group or a group of the formula
in which a is 1 to 6 and b is 0 to 6, wherein the groups R may be the same or different, and wherein the values of a and b may be the same or different.
The reaction between (i) and (ii) is conveniently carried out in the presence of a suitable solvent at elevated temperature (i.e. above ambient temperature (20° C.)), e.g. in the temperature range 120 to 240° C., more particularly 140 to 200° C., often under reflux conditions and, where necessary, at elevated pressure, e.g. in the range from 2 to 100×10
5
Pa. Examples of solvents include hydrocarbon solvents such as higher alkanes, toluene, xylene, mesitylene, e.g “SHELLSOL” (trade mark) A solvent available from member companies of the Royal Dutch/Shell Group of Companies; also synthetic and mineral oils such as “HVI-60”; ether solvents such as tetrahydrofuran and 1,4-dioxane; nitriles such as acetonitrile; alcohols such as 1-pentanol (amyl alcohol) and 2-methyl-2-propanol (tert-butyl alcohol); and chlorohydrocarbons such as 1,1,1-trichloroethane. The process may be carried out in the absence of a solvent but, as indicated above, is conveniently carried out in the presence of one. Any water or excess of alcohol may be removed using for example a Dean and Stark trap.
The molar ratio (i):(ii) in the process of the present invention is preferably in the range from 1:1 to 4:1, more preferably from 1:1 to 3:1, most preferably from 1:1 to 2:1.
The reaction product of the present invention may be used as an additive in lubricating oils. Accordingly, the present invention provides a lubricating oil composition comprising a major amount (more than 50% w) of a lubricating base oil and a minor amount (less than 50% w),
Crane Anthony E.
Scott Richard M.
Infineum USA L.P.
Johnson Jerry D.
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