Linear compounds containing phenol and salicylic acid units

Details Linear compounds containing phenol and salicylic acid units Linear compounds containing phenol and salicylic acid units

2001-03-09

2003-07-22

Medley, Margaret (Department: 1714)

Fuel and related compositions

Liquid fuels

Containing organic -c

C044S403000, C044S386000, C508S331000, C508S479000, C508S510000, C560S057000, C560S070000, C560S071000, C562S468000, C562S476000, C562S477000

Reexamination Certificate

active

06596038

ABSTRACT:

TECHNICAL FIELD
This invention relates to linear compounds in the form of oligomers or polymers containing unsubstituted or substituted phenol units and unsubstituted or substituted salicylic acid units. These compounds are useful as additives for lubricants and fuels. Metal salts of these compounds are useful as lubricant additives.
BACKGROUND OF THE INVENTION
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 from other fluids such as lubricating oils used in the aircraft. The fuel is thus maintained for long periods at high temperatures. This results in discoloration and decomposition which produce soluble colored products and insoluble products such as gums, sediments and granular material. The insoluble products can form deposits that reduce the heat exchange capacity and can block filters potentially causing loss of power. Soluble colored by-products are unsightly and an indication of decomposition.
In some oil fired devices, such as boilers and slow heating cookers, e.g. the Aga type, kerosene 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 manufactures of such devices have for many years recommended to their users that at least once each six months such pipe parts are cleaned of solid deposits of coke or other materials.
The problem therefore is to provide enhanced thermal stability to these fuels. The present invention provides a solution to this problem. The addition of the inventive compounds to these fuels enhances the thermal stability of such fuels.
International publications WO 99/25677 and WO 99/25793 disclose calixarenes containing within the calixarene ring at least one salicylic acid. The use of these compounds as fuel additives and lubricant additives is disclosed. Metal salts of these compounds as well as the use of such metal salts as lubricant additives are disclosed. These references indicate that in order to provide the calixarene ring structure it is necessary to use a reaction mixture containing at least 50% by weight solvent, preferably at least 80% by weight solvent, more preferably at least 90% by weight solvent. The references indicate that at solvent concentrations well below 50% by weight linear molecules are formed.
SUMMARY OF THE INVENTION
This invention relates to a linear compound comprising m units of formula (I)
and n units of the formula (II)
joined together, each end of the compound having a terminal group which is independently one of the following
wherein in formulae (I)-(IV), Y is a divalent bridging group which may be the same or different in each unit; R
0
is hydrogen or a hydrocarbyl group, R
5
is hydrogen or a hydrocarbyl, j is 1 or 2; R
3
is hydrogen, a hydrocarbyl or a hetero-substituted hydrocarbyl group; 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; m is at least 1; n is at least 2; the ratio of m to n ranges from about 0.1:1 to about 2:1, the total of m+n is at least 3; the linear compound containing at least one block unit containing at least two units corresponding to formula (II) attached to each other, the linear compound being formed in a reaction mixture optionally containing an organic solvent, the concentration of the organic solvent in the reaction mixture being up to about 48% by weight of the reaction mixture. The invention further provides for metal salts of the foregoing compounds. The linear compounds are useful as fuel and lubricant additives. The salts are useful as lubricant additives.
The inventive linear compounds, at least in one embodiment, are useful in the inventive lubricating oil compositions as surfactants and/or antioxidants. They are useful in the inventive fuel compositions, at least in one embodiment, as thermal stabilizers.
The metal salts of the inventive linear compounds are useful in the inventive lubricating oil compositions, at least in one embodiment, as detergents. The metal salts are also useful, at least in one embodiment, in reducing black paint in low- or medium-speed diesel engines.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The term “hydrocarbyl” denotes a group having a carbon atom directly attached to the remainder of the molecule and having a hydrocarbon or predominantly hydrocarbon character within the context of this invention. Such groups include the following:
(1) Purely hydrocarbon groups; that is, aliphatic, (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl or cycloalkenyl), aromatic, aliphatic- and alicyclic-substituted aromatic, aromatic-substituted aliphatic and alicyclic groups, and the like, as well as cyclic groups wherein the ring is completed through another portion of the molecule (that is, any two indicated substituents may together form an alicyclic group). Such groups are known to those skilled in the art. Examples include methyl, ethyl, octyl, decyl, octadecyl, cyclohexyl, phenyl, etc.
(2) Substituted hydrocarbon groups; that is, groups containing non-hydrocarbon substituents which do not alter the predominantly hydrocarbon character of the group. Those skilled in the art will be aware of suitable substituents. Examples include hydroxy, nitro, cyano, alkoxy, acyl, etc.
(3) Hetero groups; that is, groups which, while predominantly hydrocarbon in character, contain atoms other than carbon in a chain or ring otherwise composed of carbon atoms. Suitable hetero atoms will be apparent to those skilled in the art and include, for example, nitrogen, oxygen and sulfur.
In general, no more than about three substituents or hetero atoms, and preferably no more than one, will be present for each 10 carbon atoms in the hydrocarbyl group.
The terms “hydrocarbon” and “hydrocarbon-based” have the same meaning and can be used interchangeably with the term hydrocarbyl when referring to molecular groups having a carbon atom attached directly to the remainder of a molecule.
The term “lower” as used herein in conjunction with terms such as hydrocarbyl, alkyl, alkenyl, alkoxy, and the like, is intended to describe such groups which contain a total of up to 7 carbon atoms.
The term “oil-soluble” refers to a material that is soluble in mineral oil to the extent of at least about one gram per liter at 25° C.
The term “TBN” refers to total base number. This is the amount of acid (perchloric or hydrochloric) needed to neutralize all or part of a material's basicity, expressed as milligrams of KOH per gram of sample.
The Linear Compounds
The inventive linear compounds are in the form of linear oligomers or polymers. These compounds are comprised of units represented by formulae (I) and (II) connected to each other. At each end of the compound is a terminal group which is independently represented by the formulae (III) or (IV). The units represented by formulae (I) and (II) may be distributed in random or block patterns, with the proviso that at least one block of units consisting of two or more units represented by formula (II) must be present. For example, the linear compounds must include one or more block of units corresponding to -(II)(II)-, -(II)(II)(II)-, -(II)(II)(II)(II)-, etc. Examples of the inventive compounds include the following
(III)-(II)-(II)-(II)-(I)-(II)-(III)
(III)-(II)-(I)-(I)-(II)-(II)-(II)-(IV)
(IV)-(I)-(I)-(II)-(II)-(II)-(I)-(III)
(III)-(II)-(II)-(I)-(II)-(II)-(III)
(IV)-(I)-(II)-(II)-(II)-(II)-(II)-(IV)
(III)(II)(II)(II)(II)(II)(II)(I)(II)(II)(II)(IV)
(IV)((II))
10
(I)((II))
5
(I)(I)((II))

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