US2568876A - Reaction products of n-acylated polyalkylene-polyamines with alkenyl succinic acid anhydrides - Google Patents

Reaction products of n-acylated polyalkylene-polyamines with alkenyl succinic acid anhydrides Download PDF

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US2568876A
US2568876A US12727849A US2568876A US 2568876 A US2568876 A US 2568876A US 12727849 A US12727849 A US 12727849A US 2568876 A US2568876 A US 2568876A
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succinic acid
acid
acid anhydride
reaction
product
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Ralph V White
Henry D Norris
Phillip S Landis
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ExxonMobil Oil Corp
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ExxonMobil Oil Corp
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Description

Patented Sept. 25, 1951 NHTED STATES 2,568,876 GFFICE REACTION PRODUCTS F N-ACYLATED POLYALKYLENE-POLYAMINES WITH ALKENYL SUCCINIC ACID ANHY- DRIDES No Drawing. Application November 14, 1949, Serial No. 127,278

23 Claims. i

This invention relates, broadly, to organic nitrogen compounds and to corrosion-inhibiting compositions containing the same. It is more specifically concerned with the reaction products obtained by reacting monocarboxylic acids, polyalkylenepolyamines having one more nitrogen atom per molecule than there are alkylene groups in the molecule, and alkenyl succinic acid anhydrides; and with corrosion-inhibiting compositions comprising suitable vehicles containing these reaction products.

As is well known to those familiar with the art, whenever machines and devices have been constructed in whole or in part of metals, particularly ferrous metals, the occurrence of surface corrosion has presented serious problems. For example, farming implements are frequently stored under conditions where they are subject to rusting. Rusting also presents problems in the storage of infrequently used machinery, in the shipment of machined metal parts, such as sewing machine parts and gun barrels, and in the use of structural steel members, such as bridge trusses. These difi'iculties have been overcome in part by coating the exposed surfaces with paints, greases, oils and the like. In many cases, however, it has been disadvantageous to use these expedients since it is often necessary to remove such coatings completely before the object is used. Accordingly, recourse has been had to corrosion-inhibiting compositions which can be applied to metal surfaces and which can be removed easily and cheaply.

In the field of lubrication, the rusting of ferrous metal surfaces has been a common occurrence. This has been a serious problem in steam turbines, particularly during the initial operation of new installations. The rusting is most pronounced at points where the clearance between bearing surfaces is very small, such as in the governor mechanism. This is usually caused by water entering the oil supply, as by condensation, and becoming entrained in the oil throughout the circulating system, thereby coming into contact with the ferrous metal surfaces. Manifestly, this constitutes a menace to the operational life of the turbine.

Many materials have been proposed as coating compositions or as addition agents for lubricating oils to inhibit rusting. In United States Letters Patents Nos. 2,124,628, 2,133,734 and 2,279,688, there were disclosed alkenyl succinic acids, and halogenated and/or sulfurized derivatives thereof, as compounds useful in the prevention of corrosion. In these patents, the patentees stipulate that the acids must have at least 16 carbon atoms, and preferably, 20 carbon atoms per molecule.

It has now been found that a. new type of corrosion inhibitor can be produced from alkenyl succinic acid anhydrides having any number of carbon atoms in the alkenyl radical thereof. It has now been discovered that useful corrosion inhibitors can be produced by first reacting a monocarboxylic acid with a polyalkylenepolyamine to produce an intermediate product, and then reacting this intermediate product with an alkenyl succinic acid anhydride.

Accordingly, it is a broad object of this invention to provide novel corrosion inhibitors. Another object is to provide corrosion inhibitors produced from alkenyl succinic acids having any number of carbon atoms in the alkenyl radical. A specific object is to provide corrosion inhibitors by reacting a monocarboxylic acid with a polyalkylenepolyamine to produce an intermediate product, and then reacting this intermediate product with an alkenyl succinic acid anhydride. A more specific object is to provide substantially neutral vehicles containing such corrosion inhibitors. An important object is to provide mineral lubricating oils containingminor amounts of corrosion inhibitors of the type described hereinbefore. Other objects and advantages of the present invention will become apparent to those skilled in the art from the following detailed description.

Broadly stated, the present invention provides new compositions of matter obtained by reacting a monocarboxylic acid with a polyalkylenepolyamine having one more nitrogen atom per molecule than there are alkylene groups in the molecule, in a molar proportion varying between about one and about (ac-1) to one, respectively, wherein :2 represents the number of nitrogen atoms in the polyalkylenepolyamine molecule, to produce an intermediate product, and reacting an alkenyl succinic acid anhydride with the intermediate product, in a molar proportion varying between about (a:l) to one, respectively; the sum of the number of moles of the monocarboxylic acid and of the alkenyl succinic acid anhydride reacted with each mole of said polyalkylenepolyamine being no greater than 11:. The present invention provides also a substantially neutral vehicle containing between about 0.003 per cent and about 50 per cent by weight of these compositions of matter.

In general, the polyalkylenepolyamine reactants utilizable herein are those compounds having the structural formula, H2N(RNH) =H, wherein R is an alkylene radical, or a hydrocarbon radical-substituted alkylene radical, and z is an integer greater than one, there being no upper limit to the number of alkylene groups in the molecule. It is preferred, however, to use the polyethylenepolyamines. because of their greater commercial availability. These compounds have the formula:

wherein z is an integer varying between about two and about six. In naming the polyalkylenepolyamine reactants, the nitrogen atoms are considered to be attached to the terminal carbon atoms of the main carbon atom chain indicated in each compound name. For example, di-(lmethylamylene) triamine has the structural formula:

acrylic acid; nitrosobutyric acid; aminovaleric acid; aminohexanoic acid; heptanoic acid; heptanoic acid anhydride; 2-ethylhexanoic acid; a.- bromooctanoic acid; decanoic acid; dodecanoic In numbering the main carbon atom chain, the carbon atom attached to the terminal --NH2 radical is designated as the carbon atom in the 1-position. Similar alkylene groups recur throughout the molecule. Non-limiting examples of the polyalkylenepolyamine reactants are diethylenetriamine; triethylenetetramine; tetraethylenepentamine; di (methylethylene)triamine; hexapropyleneheptamine; tri-(ethylethylene) tetramine; penta-(l-methylpropylene) -hexamine; tetrabutylenepentamine; hexa-(l,1-dimethylethylene) -heptamine; di- (l-methylbutylene) triamine; pentaamylenehexamine; tri-(1,2,2- trimethylethylene) tetramine; dil -methylamylene) triamine; tetra (1,3 dimethylpropylene) pentamine; penta-(1,5-dimethylamylene) hexamine; di-(1-methyl-4-ethylbutylene) -triamine; penta (1,2 dimethyl-l-isopropylethylene) hexamine; tetraoctylenepentamine; tri-(1,4-diethylbutylene) tetramine; tridecylenetetramine; tetra- (1,4-dipropylbutylene)pentamine; didodecylenetriamine; tetratetradecylenepentamine; penta- (1-methyl-4-nonylbutylene) hexamine tril ,15- dimethylpentadecylene) -tetramine; trioctadecylenetetraamine; dieiccsylenetriamine; di- (1,2-dimethyl l4 nonyltetradecylene) triamine; di- (1,18 dioctyleetedecylenel triamine; penta (1- methyl benzylethylene) hexamine; tetra-(1- methyl 3 benzylpropylene) pentamine; tri-(lmethyl-l h:.ny1-3 propylpropylene) tetramine; and tetra- (l-ethyl-Z-benzylethylene) pentamine.

The poiyalkyieizepalyamines can be prepared by sever-7:1 methods well known to the art. One well accepted method comprises reacting ammonia with an alkyl, or substituted alkyl, dihalide. For example, tetraethylenepentamine has been prepared by reacting ammonia with ethylene bromide.

Any monocarboxylic acid, or its acid anhydride or acid halide, can be reacted with the polyalkylenepolyamine reactant to produce the intermediate products used in preparing the reaction products of the present invention. The aromatic and the heterocyclic monocarboxylic acids, as well as the aliphatic monocarboxylic acids, are utilizable. Monocarboxylic acids containing substituent groups, such as halogen atoms, are also applicable herein. However, the preferred monocarboxylic acid reactants are the aliphatic monocarboxylic acids, i. e., the saturated or unsaturated, branched-chain or straight-chain, monocarboxylic acids, and the acid halides and acid anhydrides thereof. Particularly preferred are the aliphatic monocarboxylic acid reactants having a relatively long carbon chain length, such as a carbon chain length of between about 10 carbon atoms and about 30 carbon atoms. Nonlimiting examples of the monocarboxylic acid reactant are formic acid; acetic acid; fiuoroacetic acid; acetic anhydride; acetyl fluoride; acetyl chloride; propionic acid; propiolic acid; propionic acid; undecylenic acid; tetradecanoic acid; myristoyl bromide; hexadecanoic acid; palmitic acid; oleic acid; heptadecanoic acid; stearic acid; linoleic acid; linolenic acid; phenylstearic acid; xylylstearic acid; .a-dodecyltetradecanoic acid; arachidic acid; behenic acid; behenolic acid; erucic acid; erucic acid anhydride; cerotic acid; selacholic acid; heptacosanoic acid anhydride; montanic acid; melissic acid; ketotriacontanoic acid; hexahydrobenzoic acid; hexahydrobenzoyl bromide; furoic acid; chlorofuroic acid; thiophene carboxylic acid; picolinic acid; nicotinic acid; benzoic acid; benzoic acid anhydride; benzoyl iodide; benzoyl chloride; toluic acid; xylic acid; chloroanthranilic acid; toluic acid anhydride; chlorodinitrobenzoic acid; cinnamic acid; cinnamic acid anhydride; aminocinnamic acid; salicylic acid; hydroxytoluic acid; iodosalicylic acid; naphthoyl chloride; and naphthoic acid.

Test data tend to establish that the first molecule of the monocarboxylic acid reactant which reacts with the polyethylenepolyamine reactant condenses with both a terminal nitrogen atom and the nitrogen atom adjacent thereto, with the formation of two molecules of water, to form an imidazoline ring. The other molecules of the monocarboxylic acid reactant probably react with the remaining nitrogen atoms to form acylated derivatives. No evidence has been found for the presence of more than one imidazoline ring per molecule of intermediate. The following example furnishes evidence of the imidazoline structure:

EXAMPLE I the following analysis corresponding to the empirical formula of the imidazoline compound:

Calculama Found Per cent C 68. 24 68. 08 11.85 12. 03 19. 91 19.78 Molecular Weight 211 202 A sample of Z-methylimidazoline (M. P. 104.5- C.) was prepared in accordance with the method of Ladenberg, Ber., 27, 2952 (1894). This was used as a reference compound.

An infrared spectrum was obtained on a highlyreflned white oil dispersion of the reference compound. Another infrared spectrum was obtained for liquid fraction 3. The similarity of the two spectra indicated the presence of the imldazoline ring in fraction 3. On the basis of the results of chemical analyses and of infrared absorption spectra, it is postulated that fraction 3 has the following structure:

CH2CHa In a similar manner, it can be postulated that a polypropylenepolyamine reactant will react to form a. A -tetrahydropyrimidine ring. [For example, the reaction between equimolar quantities of dipropylenetriamine and caprylic acid can produce the product:

On the other hand, polyalkylenepolyamine reactants having longer alkylene chain lengths probably will not form ring compounds. The reaction products will be acylated, however.

Accordingly, in order to produce an intermediate product which has at least one nitrogen atom free to react chemically with the alkenyl succinic acid anhydride reactant to produce mixtures of reaction products representing the complete chemical interaction of the reactants, rather than physical mixtures of alkenyl succinic acid anhydride with intermediate products and/or the reaction product representing the complete chemical interaction of the reactants, it is essential that no more than (:c2) moles of monocarboxylic acid reactant be reacted with each mole of polyalkylenepolyamine reactant, a: representing the number of nitrogen atoms in the polyalkylenepolyamine molecule. Thus, the proportion of monocarboxylic acid reactant to polyalkylenepolyamine reactant will vary between about 1:1,

respectively, and about (a:2) :1, respectively, when the reaction products, representing the complete chemical interaction of the reactants, of this invention are desired. It is especially preferred to produce intermediate products having two unreacted nitrogen atoms. To produce such intermediate products, the maximum proportion of monocarboxylic acid reactant to polyalkylenepolyamine will be (:v3) :1, respectively.

When the number of moles of monocarboxylic acid reactant is only one less than the number of nitrogen atoms in the polyalkylenepolyamine reactant, i. e., (z1) moles, the intermediate product apparently will not have any nitrogen atoms free for further reaction with the alkenyl succinic acid anhydride reactant. It has been discovered, however, that such intermediate products can be combined with the alkenyl succinic acid anhydride reactant to produce products, probably physical mixtures, which ar nevertheless utilizable in accordance with the present invention. Therefore, the proportion of monocarboxylic acid reactant to polyalkylenepolyamine reactant varies, broadly, between about 1:1, respectively, and about (:r1) :1, respectively.

For example, when tetraethylenepentamine is utilized as the polyalkylenepolyamine reactant, one, two, three, or even four moles of a monocarboxylic acid reactant can be reacted with each mole thereof, to produce intermediat products suitable for the purposes contemplated herein. If five moles of monocarboxylic acid reactant are used, there may be an unreacted mole of monocarboxylic acid reactant, and such an intermediate product is not contemplated to be within the scope of th present invention. It must be strictly understood therefore, that the intermediat products of this invention are not pure, definite chemical compounds. The available facts indicate that the reaction involved is much more complex. Evidence. has been found for the formation of the imidazoline ring or the A -tetrahydropyrimidine ring is formed. However, the precise manner of reaction of the other moles of the monocarboxylic acid reactant is purely conjectural. This is substantiated by the fact that some residual acidityis always present in the intermediate product. In view of the foregoing, it will be understood that any designation assigned to these products, other than a definition comprising a recitation of the process of producing them, is not accurately descriptive of them.

The temperature at which the reaction between the monocarboxylic acid reactant and the polyalkylenepolyamine reactant is effected is not too critical a factor. Since the reactions involved appear to be an amide-formation reaction and a condensation reaction, the general temperature conditions for such reactions, which are well known to those skilled in the art, are applicable. Nevertheless, it is usually preferred to operate at temperatures varying between about C. and about C. It must be strictly understood, however, that the reaction between the monocarboxylic acid reactant and the polyalkylenepolyamine reactant can be effected at temperatures substantially lower than 130 C. and substantially higher than 160 C., and that this invention is not to be limited to the preferred temperature range.

Water is formed as a by-product of the reaction between the monocarboxylic acid reactant and the polyalkylenepolyamine reactant. In order to facilitate the removal of this water, to effect a more complete reaction in accordance with the principle of Le Chatelier, a hydrocarbon solvent which forms an azeotropic mixture with water can be added to the reaction mixture. Heating 15 continued with the liquid reaction mixture at the preferred reaction temperature, until the removal or water by azeotropic distillation has substantially ceased. In general, any hydrocarbon solvent which forms an azeotropic mixture with water can be used. It is preferred, however, to use an aromatic hydrocarbon solvent of the benzene series. Non-limiting examples of the preferred solvent are benzene, toluene, and xylene. The amount of solvent used is a variable and noncritical factor. It is dependent on the size of the reaction vessel and the reaction temperature selected. Accordingly, a suificir-nt amount of solvent must be used to support the azeotropic distillation, but a large excess must be avoided since the reaction temperature will be lowered thereby. Water produced by the reaction can also be removed by operating under reduced pressure. When operating with a reaction vessel equipped with a reflux condenser provided with a water takeoff trap, suflicient reduced pressure can be achieved by applying a slight vacuum to the upper end of the condenser. The pressure inside the system is usually reduced to between about 50 and about 300 millimeters. If desired, the water can be removed also by distillation, while operating under relatively high temperature conditions.

The time of reaction between the -monocarboxylic acid reactant and the polyalkylenepolyamine reactant is dependent on the weight of the charge, the reaction temperature selected, and the means employed-for rmoving the water from the reaction mixture. Inpractice, the reaction is continued until the formation of water has substantially ceased. In general, the time of reaction will vary between about six hours and about ten hours.

Any alkenyl succinic acid anhydride or the corresponding acid is utilizable for the production of the reaction products of the present invention. The general structural formulae of these compounds are:

Anhydride Acid wherein R is an alkenyl radical. The alkenyl radical can be straight-chain or branched-chain; and it can be saturated at the point of unsaturation by the addition of a substance which adds to olefinic double bonds, such as hydrogen, suifur, bromine, chlorine, or iodine. It is obvious, of course, that there must be at least two carbon atoms in the alkenyl radical, but there is no real upper limit to the number of carbon atoms therein. However, it is preferred to use'an alkenyl succinic acid anhydride reactant having between about 8 and about 18 carbon atoms per alkenyl radical. In order to produce the reaction products of this invention, however, an alkenyl succinic acid anhydride or the corresponding acid must be used. Succinic acid anhydride and succinic acid are not ample, the reaction product produced by reacting an intermediate product with succinic acid anhydride is an amorphous, dark, insoluble mass. Although their use is less desirable, the alkenyl succinic acids also react, in accordance with this invention, to produce satisfactory reaction products. It has been found, however, that their use necessitates the removal of water formed during the reaction and also often causes undesirable side reactions to occur to some extent. Nevertheless, the alkenyl succinic acid anhydrides and the alkenyl succinic acids are interchangeable for the purposes of the present invention. Accordingly,-when the term alkenyl succinic acid anhydride," is used herein, it must be clearly understood that it embraces the alkenyl succinic acids as well as their anhydrides, and the derivatives thereof in which the olefinic double bond has been saturated as set forth hereinbefore. Non-limiting examples of the alkenyl succinic acid anhydride reactant are ethenyl succinic acid anhydrides; ethenyl succinic acid; ethyl succinic acid anhydride; propenyl succinic acid anhydride; sulfurized propenyl succinic acid anhydride; butenyl succinic acid; Z-methylbutenyl succinic acid anhyutilizable herein. For exdride; 1,2-dichloropentyl succinic acid anhydride; hexenyl succinic acid anhydride; hexyl succinic acid; sulfurized 3-methylpentenyl succinic acid anhydride; 2,3-dimethylbutenyl succinic acid anhydride; 3,3-dimethylbutenyl succinic acid; 1,2-dibromo-2-ethylbutyl succinic acid; heptenyl succinic acid anhydride; 1,2-diiodooctyl succinic acid; octenyl succinic acid anhydride; 2-methylheptenyl succinic acid anhydride; 4-ethylhexenyl succinic acid; 2-isopropylpentenyl succinic acid anhydride; noneyl succinic acid anhydride; 2- propylhexenyl succinic acid anhydride; decenyl succinic acid; decenyl succinic acid anhydride; 5- methyl-2-isopropylhexenyl succinic acid anhydride; 1,2-dibromo-2-ethy1octenyl succinic acid anhydride; decyl succinic acid anhydride; undecenyl succinic acid anhydride; 1,2-dichloroundecyl succinic acid; 3-ethyl-2-t-butylpentenyl succinic acid anhydride; dodecenyl succinic acid anhydride; dodecenyl succinic acid; 2-propylnonenyl succinic acid anhydride; 3-butyloctenyl succinic acid anhydride; tridecenyl succinic acid anhydride; tetradecenyl succinic acid anhydride; hexadecenyl succinic acid anhydride; sulfurized octadecenyl succinic acid; octadecyl succinic acid anhydride; 1,2-dibromo 2 methylpentadecenyl succinic acid anhydride; 8-propylpentadecyl succinic acid anhydride; eicosenyl succinic acid anhydride; 1,2 dichloro 2 methylnonadecenyl succinic acid anhydride; 2-octyldodecenyl succinic acid; 1,2-diiodotetracosenyl succinic acid anhydride; hexacosenyl succinic acid; hexacosenyl succinic acid anhydride; and hentriacontenyl succinic acid anhydride.

The methods of preparing the alkenyl succinic acid anhydrides are well known to those familiar with the art. The most feasible method is by the reaction of an olefin with maleic acid anhydride. Since relatively pure olefins are difficult to obtain, and when thus obtainable, are often too expensive for commercial use, alkenyl succinic acid anhydrides are usually prepared as mixtures by reacting mixtures of olefins with maleic acid anhydride. Such mixtures, as well as relatively pure anhydrides, are utilizable herein.

In general, the alkenyl succinic acid anhydride reactant is reacted with the intermediate prodduct in a proportion of between about (.'r.1) and about one mole of alkenyl succinic acid anhydride reactant for each mole of polyalkylenepolyamine reactant used in the preparation of the intermediate product, :1: representing the number of nitrogen atoms in the polyalkylenepolyamine reactant molecule. The sum of the number of moles of monocarboxylic acid reactant and of alkenyl succinic acid anhydride reactant reacted with each mole of polyalkylenepolyamine reactant, in accordance with this invention, must not exceed the number of nitrogen atoms in the polyalkylenepolyamine reactant molecule. Accordingly, the maximum number of moles of alkenyl succinic acid anhydride reactant used is the difference between the number of nitrogen atoms in the polyalkylenepolyamine reactant molecule and the number of moles of monocarboxylic acid reactant used per mole of polyalkylenepolyamine reactant. As mentioned hereinbefore, however, the first molecule of the monocarboxylic acid reactant appears to react with two nitrogen atoms. Accordingly, in order to achieve a reaction product which does notinvolve a physical mixture of the intermediate product and/or the reaction product, representing the complete chemical interaction of the reactants, with the alkenyl succinic acid anhydride reactant, the sum of the number of moles of the monocarboxylic acid reactant and of the alkenyl succinic acid anhydride reactant reacted with each mole of polyalkylenepolyamine reactant must not exceed one less than the number of nitrogen atoms in the polyalkylenepolyamine molecule. In order words, the proportion of alkenyl succinic acid anhydride reactant to polyalkylenepolyamine reactant will vary between (x-2) :1, respectively and 1:1, respectively. For example, when two moles of decanoic acid are reacted with one mole of tetraethylenepentamine to produce an intermediate product, one or two moles, but not more than two moles, of an alkenyl succinic acid anhydride is reacted with this intermediate product to produce a reaction product representing the complete chemical interaction of the reactants. However, three moles of an alkenyl succinic acid anhydride reactant can be reacted with this intermediate product to produce a product which comprises a physical mixture. Such a product is contemplated herein.

The reaction between the alkenyl succinic acid anhydride reactant and the intermediate product takes place at any temperature ranging from ambient temperatures and upwards. This reaction is apparently an amide formation reaction efiected by the well known addition of the anhydride group to an amino or imino group. This addition proceeds at any temperature, but temperatures of about 100 C. or lower are preferred. When an alkenyl succinic acid is used, water is formed. Therefore, in this case, the reaction temperature preferably should be higher than about 100 C.

The reaction between the alkenyl succinic acid anhydride reactant and the intermediate roduct proceeds smoothly in the absence of solvents, at atmospheric pressure. However, the occurrence of undesirable side reactions is minimized when a solvent is employed. Use of a solvent is preferable when the reaction product is to be used in a steam turbine lubricating oil. .Since a small amount of water is usually formed also when an alkenyl succinic acid anhydride is used in the reaction, the solvent employed is preferably one which will form an azeotropic mixture with water. These solvents have been discussed fully, hereinbefore, in conjunction with the reaction between the monocarboxylic acid reactant and the polyalkylenepolyamine reactant. The same solvents and the same methods of using them ar applicable to the reaction between the interperatures below 100 C. for a reaction time of less than one hour. In order to ensure complete reaction, however, it is preferred to continue heating for several hours. For example, when benzene is used as the solvent at a temperature of 100-110" C., heating is continued for about flve hours. When water is formed during the reaction, as when an alkenyl succinic acid is used, the completion of the reaction is indicated by a substantial decrease in the formation of water. In general, the reaction time will vary between several minutes and about ten hours.

Certain reaction products of this invention will be very viscous, or even solid, rendering handling very difficult from a commercial standpoint. Likewise, otherwise satisfactory antirust agents of this invention may be undesirably emulsive. These difficulties can often be alleviated by producing the reaction products in a mineral oil solution or dispersion. The mineral oil can be added to the reaction mixture of the intermediate product and alkenyl succinic acid anhydride reactant, before they are reacted with each other. In an alternate procedure, the reaction product can be produced by the methods mentioned hereinbefore, and then the mineral oil can be added to the reaction product while it is still hot. If a solvent is used, it is immaterial whether the solvent is removed before or after the addition of the mineral oil. Dependent on the type of reaction product involved and of final product desired, the mineral oil can be used in any amount, thereby producing reaction products containing from about one per cent by weight of oil up to as much as 99 per cent by weight of oil.

Without any intent of limiting the scope of the present invention, it is postulated that the reaction products, representing the complete chemical interaction of the reactants, contemplated herein, are condensation products of the polyalkylenepolyamine reactant having at least one free carboxylic acid group. For example, when one mole of acetic acid is reacted with one mole of triethylenetetramine to produce an intermediate product which is reacted with two moles of hexenyl succinic acid anhydride, it is postulated that at least the following three reaction products and isomers thereof are possible. Theoretically all three could be present in varying amounts.

mediate product and the alkenyl succinic acid anhydride reactant. For example, satisfactory CH; (I311, products of this invention have been prepared at C H C H H H temperatures varying between about 100 C. and about 110 C., using an aromatic hydrocarbon COOH 00H solvent of the benzene series. 0

The time of reaction is dependent on the size Nix-43H, tt-CH, of the charge, the reaction temperature selected, N and the means employed for removing any water C CAB from the reaction mixture. Ordinarily, the addi- (H) tion of the anhydride reactant is substantially 0 complete within a few minutes. The more emul- (H) 00H sive reaction products can be produced at tem- OOH CH2CH2 (l H CH2CH2 N N-CH2CHzN-CH2 CHzNH-CCH1 CHC-NHC Hr-CHzNCHz-CH,N I l I C =0 05H" =0 C JJH; ?Hz 5H) $11:

C(H)CQH|I 06H]! OOH OOH aceasve The reaction products probably contain other substances. Accordingly, and in the interest of brevity, the reaction products are best defined by reciting the reactants and the number of moles of each which are used in the reaction. For example, the reaction product produced by reacting one mole of oleic acid with one mole of triethylene tetramine to produce an intermediate product which is then reacted with two moles of decenyl succinic acid anhydride may be defined as the reaction product of oleic acid (I) +triethylenetetramine (I) +decenyl succinic acid anhydride (II).

In addition to the products described in the illustrative examples, set forth hereinafter, nonlimiting examples of the reaction products contemplated herein are those produced by reacting the following combinations of reactants: formic acid (IV) +tetra-(1-ethy1-2-benzylethylene) pentamine (I)+ethenyl succinic acid anhydride (1); acetic acid anhydride (I) +tri-(1-methyl- 1-phenyl-3-propylpropylene)tetramine (I) +ethenyl succinic acid (II); acetyl fluoride (I) +triethylenetetramine (I) +hexeny1 succinic acid anhydride (II); fluoroacetic acid (II) +tetra- (1-methy1-3-benzylpropylene) pentamine (I)+ ethyl succinic acid anhydride (III); propionic acid (I) +penta (1 methyl-2-benzylethylene)- hexamine (I) +propenyl succinic acid anhydride (V); propiolic acid (I) +di-(1,18-dioctyloctadecylene) triamine (I) +sulfurized propenyl succinic acid anhydride (1); fi-chloropropionic acid (II) +di (1,2-dimethyl-14-nonyltetradecylene) triamine (I) +butenyl succinic acid (I); bromoacetic acid (I) +dieicosylenetriamine (I) +2- methylbutenyl succinic acid anhydride (H); isobutyric acid (III) +trioctadecylenetetramine (I)+1,2-dich1oropentyl succinic acid anhydride (I); a-bromobutyric acid (I) +tri-(1,15-dimethylpentadecy1ene)tetramine (I) +hexeny1 cinic acid (I) isocrotonic acid chloride (I) +penta (1 methyli-nonylbutylene)hexamine (I) hexylsuccinic acid anhydride (IV); fi-ethylacrylic acid (II) +tetradecylenepentamine (I)+ sulfurized 3-methylpentenyl succinic acid anhydride (II); valeric acid (I) +didodecylenetriamine (I) +2,3-dimethylbutenyl succinic acid anhydride (I); a-bromoisovaleric acid (III)+ tetra-(lA-dipropylbutylene) pentamine (I) 3,3- dimethylbutenyl succinic acid (I); allylacetic acid (II) +tridecylene-triamine (I)+1,2-dibromo-2-ethy1butyl succinic acid (I); hexanoyl bromide (I) +tri-(1,4-diethylbutylene) tetramine (I) +heptenyl succinic acid anhydride (I); sorbic acid (IV) +tetraoctylenepentamine (I)+ 1,2-diiodoactyl succinic acid (I); fi-chloroacryli: acid (I) +penta- (1,2-dimethy1-l-isopropylethylene)hexamine (I) +octenyl succinic acid anhydride (V); nitrosobutyric acid (I) +di-(1- methyl 4-ethylbutylene) triamine (I) +2-methylheptenyl succinic acid anhydride (II); aminovaleric acid (V) +penta-(1,5-dimethylamylene)- hexamine (I) +4-ethylhexenyl succinic acid (I); aminohexanoic acid (II) +tetra-(1,3-dimethylpropylene) pentamine (I) +2 isopropylpentenyl succinic acid anhydride (III); heptanoic acid anhydride (I) +di (1 methy1amylene)triamine (I) +noneyl succinic acid anhydride (II); 2- ethylhexanoic acid (III) +tri-(1,2,2-trimethylethylene) tetramine (I)+2-propyl-hexenyl succinic acid anhydride (I); a-bromooctanoic acid (I) +pentaamylene-hexamine (I) +decenyl .succinic acid anhydride (IV); decanoic acid (I)+ d1 (1 methylbutylene)triamine (I) +deceny1 succinic acid (I); dodecanoic acid (V) +hexa- SUC- 12 (1,1 dimethylethylene) heptamine (I) +5-methy1-2-isopropylhexenyl succinic acid anhydride (II); undecylenic acid (II) +tetrabutylenepentamine (I)+1,2-dibromo-2-ethylocteny1 succinic acid anhydride (II); tetradecanoic acid (111)4- penta (l-methyl-propylene) hexamine (I) +00- tenly succinic acid anhydride (II); hexadecanoic acid (I)+tri(ethylethylene)tetramine (I)+ decyl succinic acid anhydride (III); palmitic acid (VI) +hexapropyleneheptamine (I) +undecenyl succinic acid anhydride (I); oleic acid (I) +di (methylethylene)triamine (I)+1,2 -dichloroundecyl succinic acid (I); heptadecanoic acid (IV) +tetraethylenepentamine (I) +3-ethyl-2-t-butylpentenyl succinic acid anhydride (1); stearic acid (I)+hexapropyleneheptamine (I)+ dodecenyl succinic acid anhydride (VI); linoleic acid (IV) +hexa (1,1 dimethylethylene) heptamine (I) +dodecenyl succinic acid (I); linoleic acid (I) +triethylene-tetramine (I) +2-propylnoneyl succinic acid anhydride (I11); phenylstearic acid (I) +diethylenetriamine (I) +3- butyloctenyl succinic acid anhydride (I); xylylstearic acid (II) +di-(methylethylene) triamine (I) +tridecenyl succinic acid anhydride (I); a-dodocyltetradecanoic acid (I) +diethylenetriamine (I) +tetradecenyl succinic acid anhydride (I); arachidic acid (II)+tetra-(1,3-dimethylpropylene) pentamine (I) +hexadeceny1 succinic acid anhydride (III); behenic acid (I) +tetrabutylenepentamine (I) +su1furized octadenecyl succinic acid anhydride (II); behinolic acid (III) +tetraethylene pentamine (I) +octadecy1 succinic acid anhydride (II); erucic acid anhydride (I) +hexaethyleneheptamine (I)+1,2- dibromo-2-methylpentadecenyl succinic acid anhydride (V); melissic acid (I) +diethylenetri amine (I) +8-propylpentadecyl succinic acid anhydride (I); hexahydrobenzoic acid (II)+triethylenetetramine (I) +eicosenyl succinic acid anhydride (II); hexahydrobenzoyl chloride (I) dipropylenetriamine (I) +decenyl succinic acid anhydride (1); furoic acid (I) +di-(1-methylbutylene) triamine (I) +1,2 dichloro 2-methylnonadecyl succinic acid anhydride (II); chlorofuroic acid (V) +penta-(l-methylpropylene) hexamine (I) +2-octyldodecenyl succinic acid (I); thiophenecarboxylic acid (I) +diethylenetriamine (I)+1,2-diiodotetracosenyl succinic acid anhydride (I); picolinic acid (III) +pentaamylenehexamine (I) +hexacoseny1 succinic acid (II); nicotinic acid (I) +tetraethylenepentamine (I) +hexacoseny1 succinic acid anhydride (IV); benzoic acid (HI) +tetraoctylenepentamine (I) +hentriacontenyl succinic acid anhydride (II); benzoyl iodide (I) +triethylenetetra- .nine (I) +octenyl succinic acid anhydride (H); toluic acid anhydride (I) +diethylene-triamine (I) +hentriacontenyl succinic acid (I); xylic acid (II) +penta-(1,2-dimethyl-1-isopropylethylene) hexamine (I) +hexadecenyl succinic acid anhydride (IV); chloroanthranilic acid (I) +tetraethylenepentamine (I) +8 propylpentadecenyl succinic acid anhydride (III); chloronitrobenzoic acid (I) +diethylenetriamine (I)+decenyl succinic acid anhydride (II); cinnamic acid (IV) +hexapropy1eneheptamine (I) hentriacontenyl succinic acid anhydride (II); aminocinnamic acid (II) +triethylenetetramine (I) +hexenyl succinic acid anhydride (II); salicylic acid (II) +triethylenetetramine (I) +tetradecenyl succinic acid anhydride (II); hydroxytoluic acid (I) +tri-(1,2,2,-trimethylethylene)- tetramine (I) +heptenyl succinic acid anhydride (HI); iodosalicylic acid (II)+hexapropyiene- 13 heptamine (I) +octenyl succinic acid anhydride (V); and naphthoic acid (I) +tetraethylenepentamine (I)+hexacosenyl succinic acid anhydride (IV).

The following specific examples are for the purpose of illustrating the present invention, and of demonstrating the advantages thereof. It must be strictly understood that this invention is not to be limited to the particular reactants and molar proportions employed, or to the operations and manipulations described therein. A wide variety of other reactants and molar proportions, as set forth hereinbefore, can be used. as those skilled in the art will readily understand.

The alkenyl succinic acid anhydrides used in the following specific examples, except in Example 75, are commercial mixtures of alkenyl succinic acid anhydrides in which the number of carbon atoms in the al 'enyl radical varies between specified limits. The Cs-sASAA is a mixture of hexenyl, heptenyl, and octenyl succinic acid anhydrides; Ca 1oA.SAA is a mixture of octenyl nonenyl, and decenyl succinic acid anhydrides; and C1o-12ASAA is a mixture of decenyl, undecenyl, and dodecenyl succinic acid anhydrides. These products are predominantly mixtures of relative pure anhydrides. Sometimes, however, they contain minor amounts of the corresponding alkenyl succinic acids, but these are utilizable as set forth hereinbefore.

EXAMPLE 2 Oleic acid (I) +trz'ethylenetetramine (I) C1o-12ASAA (II) One mole (282 grams) of oleic acid and one mole 146 grams) of triethylenetetramine were placed in a reaction vessel provided with a mechanical stirrer, a thermometer, and a reflux takeoff, i. e., a condenser device adapted to remove water from an azeotropic mixture thereof, as it is evolved from the reaction mixture. The reflux takeoff was filled with benzene, and the stirred reactants were heated to about 100 C. Benzene was added to the reaction mixture until refluxing occurred with the reactants at about 145 C. The reaction was continued at this temperature for about 8 hours, during which period of time 33 milliliters of an aqueous layer (primarily water) were collected. The solvent (benzene) was removed from the reaction mixture at a pot temperature of 145 C. under reduced pressure. This intermediate product had an N. N. (neutralization number=number of mg. KOH equivalent to one gram of product) of 4.0.

Forty-one grams of this intermediate product and 0.2 moles (58.8 grams) of C1o-I2ASAA were placed in a reaction vessel provided with a mechanical stirrer, thermometer, and reflux takeoff. Upon stirring, the reaction mixture became viscous, and some heat was evolved. Benzene was added to the reaction mixture, and heat was applied so that refluxing occurred with the reactants at about 105 C. After five hours, the benzene was removed by distillation at a pot temperature of 105 C. under reduced pressure Th resultant reaction product had an N. N. of 55.2. Pertinent data for the product are set forth in Table I.

EXAMPLE 3 grams) were placed in a reaction vessel provided with a mechanical stirrer, a thermometer. and a reflux takeoff in which a drying tube filled with anhydrous calcium chloride was-fitted to the top of the condenser. The reactants were heated to C., and benzene was added to the system until refluxing occurred at a pot temperature of 140-145 C. After 10 hours of reaction, 33 milliliters of water had been collected. Benzene was removed under reduced pressure at a pot temperature of C. The resultant intermediate product had an N. N. of 12.9.

Thirty-six grams of this intermediate product and 29.4 grams (0.1 mole) of C1o-12ASAA were heated to 140 C. in a reaction vessel equipped with a mechanical stirrer, a thermometer, and a reflux takeoff. Benzene was added and the rate of heating was adjusted to permit refluxing at a pot temperature of 140-145" C. for 8 /2 hours. Then the benzene was removed at a pot temperature of 140-145 C. under reduced pressure, leaving a reaction product having an N. N. of 61.3. Pertinent data for this product are set forth in Table V.

EXAMPLE4 Oleic acid (II)+tetraeth1/lenepentamine (I)+ C8-10ASAA (II) Thirty-six grams of the intermediate product of Example 3 and 25.8 grams (0.1 mole) of CZ'l0ASAA were heated in a reaction vessel equipped as described hereinbefore under a benzene reflux at a pot temperature of 140-150" C. for 8 hours. Some water (0.3 milliliter) was collected. Benzene was removed under reduced pressure at a pot temperature of 140-150 C. The resultant product had an N. N. of 48.7. Pertinent data for this product are set forth in Table V.

EXAMPLE 5 Oleic acid (II)+tetraethylenepentamine (I)+ C6BASAA (II) Thirty-six grams of the intermediate product of Example 3 and 22.3 grams (0.1 mole) of Cs-aASAA were heated to 144 C. in a reaction vessel provided with a mechanical stirrer, a thermometer, and a reflux takeoff. Benzene was added, and refluxing was maintained for 8 hours with the reactants at 140-150 C. Water (0.3 milliliter was collected. Benzene was removed under reduced pressure at a pot temperature of 140-150 C. The resultant product had an N. N. of 58.4. Pertinent data for this product'areset forth in Table V.

EXAMPLE 6 Oleic acid (l-i-diethylenetriamine (1+ CID-12ASAA (I) Oleic acid (0.1 mole) (28.2 grams) and diethylenetriamine (0.1 mole) (10.3 grams) were heated to 140 C. in a reaction vessel provided with a mechanical stirrer, a thermometer, and a reflux takeoff. Benzene was added to the system so that refluxing took place at 140-145 C. After nine hours of reaction, nine milliliters of an aqueous liquid were collected and the reaction was considered complete. The benzene was removed by distillation under reduced pressure. The intermediate product thus produced had an N. N. of 5.4.

About 18.3 grams of this intermediate product and 0.05 mole (14.7 grams) of C1o-12ASAA were heated to 105 C. in a reaction vessel provided as describedhereinbefore. Benzene was added so that refluxing was maintained for five hours 15 at a pot temperature of 1051l0 C. Water (0.5 milliliter) was collected. The benzene was removed by vacuum distillation at a pot temperature of l110 C. The resultant reaction produce had an N. N. of 46.8. Pertinent data for this product are set forth in Table VIII.

EXAMPLE 7 Oleic acid (I) +triethylenetetramine (I) C1o-12ASAA (II) in a 50-per cent oil solution A reaction product was produced in the same manner as the product described in Example 2, with the exception that 99.8 grams of mineral lubricating oil A (defined hereinafter) was added to the intermediate product and the C1o-1zASAA prior to reacting them. The resultant homogeneous mineral oil solution contained about 50 per cent by weight of the reaction product and it had an N. N. of 26.5. Pertinent data for this product are set forth in Table I.

EXAMPLES 8 THROUGH 19 Oleic acid (I) +triethyleuetetramiue (I) various ASAAS I-III) Oleic acid was reacted with triethylenetetramine, in a molar proportion of 1:1, as described in Example 2, to produce an intermediate product. Portions of this product were reacted with Cc-BASAA, Ca1oASAA, or C1o-12ASAA in various molar proportions of ASAA to triethylenetetramine and under varied reaction conditions. Pertinent data for these products are set forth in Table I.

EXAMPLES 20 THROUGH 27 Various acids (I) +triethyleuetetramiue (I) C1o-12ASAA (II) Each of a variety of monocarboxylic acids was reacted with triethylenetetramine in a molar proportion of 1:1, as described in Examples 2 through 7. The resultant intermediate products were each reacted with C1c-12ASAA, in a molar proportion of triethylenetetramine to ASAA of 1:2, respectively, as set forth in the data given in Table II.

EXAIMPLES 28 THROUGH 32 Various acids (II-III) +triethyleuetetramine (I) +C1o-12ASAA (I-II) Each of a variety of monocarboxylic acids was reacted with triethylenetetramine, as described in Examples 2 through 7, in various molar proportions. Portions of the resultant intermediate products were reacted with C1o-12ASAA in various molar proportions of ASAA to triethylenetetramine and under varied conditions, as defined in Table III.

EXAMPLES 33 THROUGH 42 Various acids (1) +tetraethyleuepentamine (I) C1o-12ASAA (I-IV) Each of a variety of acids was reacted with tetraethylenepentamine, as described in Examples 2 through 7, in a molar proportion of 1:1. The resultant intermediate products were reacted with C1o-12ASAA within a wide range of molar proportions of ASAA to tetraethylenepentamine, in accordance with the data set forth in Table IV. EXAMPLES 43 THROUGH 57 Oleic acid (II) +tetraethylenepentamine (I) various ASAAS (I-III) An intermediate product was produced in accordance with the procedure set forth in Ex- 16 ample 2, by reacting oleic acid with tetraethylenepentamine, in a molar proportion of 2:1, respectively. Portions of this product were reacted with C6-sASAA, Ca-mASAA, 01 C1o-12ASAA in various molar proportions of ASAA to tetraethylenepentamine, as set forth in Table V.

EXAMPLES 58 THROUGH 63 Various acids (II) +tetraethylenepentamine (I) Cio-12ASAA (II-III) Each of a variety of monocarboxylic acids, and a mixture of two of these acids, were reacted with tetraethylenepentamine in a molar proportion of 2:1, respectively in accordance with the procedures described in Examples 2 through 7. Portions of the resultant intermediate products were reacted with C1o-12ASAA in molar proportions of tetraethylenepentamine to ASAA varying between 1:2, respectively, and 1:3, in accordance with the data set forthin Table VI.

EXAMPLES 64 THROUGH 68 Various acids (III-IV) +tetraethylenepeutamine (I) +C1c-12ASSA (I-II) Each of a variety of monocarboxylic acids. and a mixture of two of these acids, were reacted with tetraethylenepentamine, in molar proportions varying between 3:1, respectively, and 4:1, by the procedures described in Examples 2 through 7. The resultant intermediate products were reacted with 010-12ASAA in molar proportions of tetraethylenepentamine to ASSA varying between-about 1:1, respectively, and 1:2, as defined by the data given in Table VII.

EXAIVIPLES 69 THROUGH 74 Various acids (I-II) +diethylenetriamine (I) C1o-12ASSA (I-II) Each of a variety of monocarboxylic acids was reacted with diethylenetriamine, by the procedures described in Examples 2 through 7, in molar proportions of 1:1, respectively, to 2:1, respectively. Portions of the resultant intermediate products were reacted with C1'o-12ASAA. in molar proportions of diethylenetriamine to ASAA varying between 1:1, respectively, and 1:2, respectively. Pertinent data for these products are set forth in Table VIII.

EXAIVIPLE75 Oleic acid (I) +triethylenetetramine (I) +iriisobutenyl succinic acid anhydride (II) in a 50- per cent oil solution Single-distilled oleic acid (red oil) (2 moles) (564 grams) and triethylenetetramine (1.5 moles) (219 grams) were placed in a reaction vessel which was provided with a stirrer, a thermometer, and a reflux takeofi trap. The refiux takeofi was filled with benzene and the stirred reactants were heated to C. Then, 30 milliliters of benzene were added to the reaction mixture such that refluxing occurred with a pot temperature of 140-142 C. The reaction was continued for ten hours, during which time 57 milliliters of an aqueous layer (primarily water) was collected. The solvent was removed from the reaction mixture by distillation at a pot temperature of C., and under about 20 millimeters pressure. This intermediate product had an N. N. of 5.5 and an average molecular weight of about 484.

About 0.466 moles (225.7 grams) of'this ir -rcatalyticallyed rusting of bout 50 per cent, rust agent.

18 This product contained a per cent and 0.008 per cent of product in a leaded, gasoline completely inhibit n the ASTM rust test, using F. This is a. modification valuate antirust agents in Blends of 0.002 per cent in the eel: permitted about 5 per cent face to rust. Pertinent test data in lubricating oils are set forth by weight, of the active anti Blends of 0.004

this reaction the metal specimens i distilled water at 80 of this test used to e light products.

of the metal sur for this product in Table IX.

m same gasoline st TABLE I hydride (produced in ac- U. 3. Patent No. 2,380,699), and

ral oil B (defined hereinafter) action vessel. The reaction 5 cracked meter, a stirin turn, was cona trap, and a vacuum e reaction ves- The reaction for three Pertinent data for the products: Olelc acid (I) +lriethulenetetrami1w (I)+uuriu8 ASAAS (I-III) intermediate product.

The reaction product had an N. N. of

1 condliltitlms for reaciigon of ASAA with 1 'Iriet y enetetram e. I Tested without oxidation inhibitors.:

00 grams of mine 24 l 2 .24 n m u m m B Cwmfi mll n w w 67 M77 U l l a m m I m M C N m m B B. m m mt id .x m mmmm ram 3%.... m xm m am umna mm mm m n "mm m .3 C E .1 c m pm 0 m M m T Dw T Dw I y d .r 00 an 0 m W m m m m m m m mm. mm m u u m m m Dw m Tun w u R t l r WWW wm WNOOOOOOOOOMMOOOMUOOIE MMM M 0000 m MW Mm mm OWOOW R m m M W 0 u M M w A H AAAAA w AAAAAAABBBAAAAAAAAAAA m w AAAAAAAA 0 s 1 m 0 %m%%%%mwm%% MMMMMJMM u W mm wmmmm m aodddcaddodddaaddd ao w m n 00000000 P00 00 0 0 0 cm .2. .32... m c e I 61060 .0 6336 53 4532 5 .1 n .m y 3 2 7 1410 m d 1N ma an aw. name a mm M w mama mm m mm mac PUN m P N W r w a m rw aim: e III a 1 r e 1 v I: 1 v e Z S to Q0 mm \/e d S o U. n a M0000 m 3 an mm mama n m .M mm m Wm afi m R Bx IIIH N M m R .r m 0 i n i 8 535 m m". 53 88 1355 5 .5 H H W m m m "W 3 O .i W 1H I TH T 1 E D n T E m i t a Wm %%M% B m MMWM 6 A m c n A s m n. mmmm m p 11 1111 11 11-V1 1 1 T M Mm m T d m W. w R m 8 m a R e a m R e.. m M d M T u G T 11 1 m M W 0 C t H 0 11111111 11111 11 1111 H1 nd 18 3 C G 8 221223.... I m f I 1. m 17 $222 22 2222 2M2 W M V mW m 22222222 m M mmmMm 2m111 o 2 2 m o m nm a w Mn m M w a w P A w a A t H d m 6 junta". o ruin: u m m ammo mama w m m m. M unwnuwww m m M mm 000%. HH 0mm 0 m. m mm m S wmiwwiii m n. M CC CCCC CC CCCC C C W W A CCCCCCCC m M m I] 1 11 I. 0 11111 11 1111 11 1111 1 1 O 1 E 03 111 1.41 r If 1 e I. flw mm 11 R111 LP. lhhl 1 1 o e M 11111111 M m. 22232 1 .i 0.... i mm mm w m mfl S m Mh m P AA A imq m P A A a n M m m m m m e i e m A m m m m m m m mma P .m m m m n .m m T0 00 00 0 0 ndu TTTT TT tmr m d dd dd d d mn m m EEEEEEEE m m m A T n h n n M u m om A TTTTTTTT m P n U h h u 0 0 mm a m T I u amm m u G nni" m w w I I n 0 m m a 6 mam ma m H u a n m mm a m mmmmmmma a a a a t a a ama a area m m u h 5 0 n cflc ro 0 m m m m n wmfi DDOPOHPF hm m m 89 an 1 m m maaaaaam m mediate, 1.074 moles (285.7 grams) of triisobutenyl succinic acid an cordance with were placed in a-re' vessel was equipped with a thermo rer, and an outlet tube which nected to a manometer,

pump. The reactants were heated, with stirring, to C. and the pressure in th sel was reduced to 50 millimeters.

was continued under these conditions hours.

TABLE VII Pertinent data for the produds: various acids (fll-m-Hetradhulenepentamim (I) +01o- ASAA (I-II) Rust Test Emulsion I Molar PMolar Reaction Conditions P d P MPei' gent'd Test, Break,

roporroporro er eta uste Min. Ex. fig Amine tion, ASAA tion, uct, Cent on Acid to ASAA to N. N. Concn Amine Amine Temp., Time, Water ea ist. ist. 1%

C. Hrs. Remover Water Water Water NsCl Cc. Cc. 64 Olelc TEPA 3:1 010-12- 1:1 145-150 6 Benzene- 35.8 0.05 A 36 40 65 do -do 3:1 Clll--- 2:1 145-150 6 o 61.1 0.05 A 0 77 55 66 Dodecanoicu 0..... 3:1 010-12". 2:1 140 8 0 55.8 i 20 0 27 5 67 l-Olelc-l-2- do"-.. 3:1 10l!--- 2:1 140 10 do. 68.2 0.05 A 0 0 17 43 Dodecanc. as Oleic .--do----. 4:1 l0-lI--- 2:1 105 5 do- 77.0 0.05 A 0 0 77 76 1 Conditions for reactions 0! ASAA with intermediate product. I Tetraethylenepentemine.

TABLE VIII Pertinent data for the products: various acids (II1')+diethulendriamim (I)+C1o-1:ASAA (I-II) Rust Test Emulsion Iltioinr PMolar Reaction Conditiona P d P MPe;I(2ent d Testfimlxilreak,

roporroporro er eta uste Ex. fi a Amine tion, ASAA tion, uct, Cent Oil Acid to ASAA to N. N Conan Amine Amine Temp., Time, Water Sea Dist. Dist. 1%

0. Hrs Remover Water Water Water NaOl Cc. Cc. 69 0le1c DETAZ 2:1 C o-u. 1:1 105-110 5 Benzene. 80.5 0.05 A 72 75 70 0....... .do 1:1 Clo-1e.-. 2:1 105 5 do 132.0 0.05 A 54 71 do 0..... 1:1 Clo-1a.-. Ltd 140 2-3 Vacuum. 20.0 i 36 72 Oetadecanoic. .do.... 1:1 Clo-1s... 1.6:1 140 5 Xylene. 30.1 8103 i 2 2 .1 73 .do do. 1:1 010-12- 2:1 140 6 do 56.8 0.05 A 10 18 6 Oleic do. 1:1 Cit-1s... 1:1 105 5 Benzene. 46.8 0.05 A 70 66 74 Dodecanoic o. 1:1 Clo-n..- 2:1 105 5 0..... 141.1 0.05 A 5 3 1 Conditions for reaction 01 ASAA with intermediate product. 5 Diethylenetrlamine.

8 Tested without oxidation inhibitors.

4 Dispersion in mineral oil.

TABLE IX Test data for product of Example 76 in oil In order to demonstrate the outstanding properties of the reaction products of this invention, typical rust test data and emulsion test data were obtained for mineral lubricating oil blends containing the reaction products described in the examples. Pertinent data are set forth in Tables I through IX.

Mineral oil A used in these tests was a blend of solvent-refined, Mid-Continent residual stock with a. solvent-refined Mid-Continent (Rodessa) distillate stock. It had a specific gravity of 0.872, a flash point of 445 F., and a Saybolt Universal viscosity of 407.! seconds at 100 F. Mineral oil B was a furfural-refined, Mid-Continent (Rodessa) distillate stock. It had a specific gravity of 0.860, a flash point of 405 F., and a Saybolt Universal viscosity of 155 seconds at 100 F. Both of these mineral lubricating oils are suitable for use in steam turbines. Unless otherwise indicated in the tables, the test oil contained 0.2

per cent by weight of 2,6-di-t-butyl-4-methyl Rust Test Emulsiml phenol and 0.1 per cent by weight of phenyl- Per 5322. i fi' a-naphthylamine, both well-known antioxidants.

g Cent on The test method used to distinguish the rustsea Dist Dist 1PM mg charactenstws of lubricating 011 blends was Water Water Water the ASTM test D665-44T for determining Rust Preventing Characteristics of Steam Turbine 0 10 A 15 Oils in Presence of Water, in which synthetic 01075 A 14 sea water was used as well as distilled water.

3-82 The synthetic sea water contained 25 grams of 0101 B .1 sodium chloride, 11 grams of magnesium chlogfig i; ride hexahydrate, 4 grams of sodium sulfate, and

0.003 B 1.2 grams of calcium chloride per liter. Ir. this 8:33? I g test a cylindrical polished steel specimen is suspended and soaked in 300 cubic centimeters of the oil under test at 140 F. for thirty minutes. Thirty cubic centimeters of synthetic sea Water (or distilled water) are added and the mixture is stirred at 1000 R. P. M. After 48 hours, the steel specimen is removed and examined for evidence of rust on the portion of the specimen which hangs in the oil. In the tables, rust test results are given in terms of per cent of exposed metal surface which has rusted. The complete rusting which is evident when uninhibited base oils are tested is taken as per cent.

The emulsion test used is the emulsion test for lubricating oils, Federal Stock Catalog, section IV, part 5. Federal Specifications VV-L-791b, February 19, 1942. In test method 320.13, 40 cubic centimeters of oil and 40 cubic centimeters of emulsant in a 100-cubic centimeter cylinder are stirred with a paddle at 1500 R. P. M., for 5 minutes, at 130 F. Separation of the emulsion is observed while the cylinder is kept at 130 F. The figures in the tables show the number of minutes at which there is no continuous layer of emulsion between the oil and the emulsant, or the number of cubic .centimeters of emulsion persisting at the end of thirty minutes.

From the data set forth in the tables, it will be apparent that goodv antirust characteristics are imparted to lubricating oils which contain the reaction products of the present invention. To be completely acceptable for use in a turbine oil, an additive, preferably, should not impart undesirable emulsion characteristics thereto. It will be apparent from the emulsion test data given in the tables that, as a class, the reaction products of this invention do not impart undesirable emulsion characteristics to the oil. Some products, however, do produce emulsive oils. Several demulsifying agents are known, however, and incorporation of such agents in these emulsive oils improves the emulsion char-' acteristics thereof.

EXAIVIPLE '16 The rusting characteristics of a mineral lubricating oil containing the product of Example 11 (Table I) were further tested, along with the oxidation characteristics thereof, by means of the ASTM test method D943-4'7T. In accordance with this test, the oil and distilled water are placed in a large test tube, which is maintained at 203 F. A polished copper-iron catalyst coil is inserted into the oil, but it does not extend into the water layer. Oxygen gas is passed through the water and oil at the rate of three liters per hour throughout the 1000-hour test period. Test oil B contained by weight 0.05 per cent of the product g Example 11, 0.2 per cent 2,6-di-tbutyl-4-methyl-pheno1, and 0.1 per cent phenyle-naphthylamine was not oxidized in this test as evidenced by an N. N. of 0.02. The catalyst coil showed no trace of rust. When the oil is tested without the antirust additive the catalyst coil rusts within as short a period of time as twentyfour hours.

EXAMPLE 77 Prevention of atmospheric corrosion In order to evaluate the new reaction products as coating compounds for the prevention of atmospheric corrosion, a test was run as follows: Two polished steel specimens were coated with the product of Example 13 (Table I) by dipping them in a two per cent by weight solution of the product in benzene. Likewise, two additional specimens were coated with the product of Example 3 (Table V). A fifth specimen was left uncoated, as the control. These specimens were suspended in the chemical laboratory, exposed to the various vapors and fumes ordinarily found therein. After 15 days of such exposure, none of the specimens showed visible signs of corrosion. Then each specimen was immersed in distilled water for about 30 seconds, by raising a separate beaker of distilled water under each one. The control specimen showed a light surface rusting about five minutes after this treatment. The coated specimens remained free of corrosion. After one hour, the immersion process was repeated. Seven days thereafter, the coated specimens were still free of any trace of corrosion. The control specimen, on the other hand, was severely corroded.

In the foregoing specific illustrative examples,

the effectiveness of the reaction products for the prevention of rust in lubricated systems and for the prevention of atmospheric corrosion has been demonstrated. In addition to the use in turbine oils or as coating agents, these reaction products are utilizable for numerous purposes. They can be added to a wide variety of vehicles to produce improved compositions. They can be dissolved in the vehicle, or they can be dispersed therein, in the form of suspensions or emulsions.

The vehicles can be liquids or plastics, the basic requirement being that they must be spreadable over metal surfaces. Spreading may be accomplished by immersion, flooding, spraying, brushing, trowelling, etc. Additionally, the vehicle should be substantially neutral. It can be oleaginous, i. e., substantially insoluble in water, or it can be aqueous. Aqueous vehicles include aqueous solutions of liquid, such as alcohol-water mixtures and the like. Oleaginous vehicles can be hydrocarbon materials, such as mineral oils and hydrocarbon solvents, or non-hydrocarbon materials, such as fatty oils and fats.

Non-limiting examples of suitable vehicles for the additives of this invention are mineral lubricating oils of all grades; gasolines and other li ht petroleum products, such as fuel oil; water; alcohols, such as ethanol, isopropanol, butanol, cyclohexanol, methylcyclohexanol, octanol, decanol, dodecanol, hexadecanol, octadecanol, oleyl alcohol, benzyl alcohol, etc.; phenols; glycols, such as ethylene glycol, propylene glycol, butylene glycol, glycerol, etc.; ketones, such as acetone, methyl ethyl ketone, dipropyl ketone, cyclohexanone, etc.; keto alcohols, such as acetol; ethers, such as d'ethyl ether, dipropyl ether, diethylene dioxide, dichloro diethyl ether, diphenyl oxide, diethylene glycol, triethylene glycol, ethylene glycol monobutyl ether, etc.; natural esters, such as ethyl acetate, butyl propionate, cresyl acetate, dodecyl acetate, ethyl maleate, butyl stearate, tridecyl phosphate, tributyl trithiophosphate, triamyl phosphite, etc.; petroleum waxes, such as slack wax and parafiin wax; natural waxes, such as carnauba wax, japan wax, beeswax, etc.; natural fats and oils, such as sperm oil, tallow, cottonseed oil, castor oil, linseed oil, tung oil, soy bean oil, oiticica oil, tar oil, oleo oil, etc.; hydrocarbons and halogenated hydrocarbons, such as butanes, chlorinated hexanes, octanes, brominated decanes, dodecanes, Freon, eicosane, benzene, toluene, xylene, cumene, indene, alkyl naphthalenes, etc; greases; asphalts; chlorinated petroleum fractions, such as chlorowax; and paints, varnishes and the like.

As those skilled in the art will readily appreciate, the applications of the compositions of the present invention are many. Lubricating oils of all types usually permit corrosion of metal surfaces. This poses a problem in the lubrication of all types of engines, particularly steam turbines. Lubricating oils containing the reaction products of this invention are effectively inhibited against such corrosion. Diesel fuels containing these additives will have less tendency to corrode injection nozzles. Steam cylinder oils and cutting oils can be inhibited against corrosive tendencies by the addition thereto of these new additives, particularly the more emulsive types. Greases can be inhibited likewise. Additionally, the more emulsive products of this invention can be substituted in whole or in part for the emulsifying agents commonly used in compounding greases, cutting oils, steam cylinder oils, etc. Hydraulic systems can be protected against corrosion by using hydraulic fluids containing the additives of the present invention.

The storage of infrequently used machinery, and the shipment and storage of metal shapes and metal parts, such as machined sewing machine parts or gun parts, present corrosion problems. Such corrosion can be prevented by treating them with slushing oils containing the additives of this invention, by coating them with organic solvent solutions or dispersions of these additives, such as the benzene solutions described hereinbefore, or by treating the surfaces thereof with dispersions of these additives in water. Corrosive tendencies of coolants and antifreeze solutions or mixtures, such as those used as coolants in internal combustion engines, can be reduced by addition thereto of the reaction products of this invention. Such antifreezes include water, alcohol-water, glycols, glycol-water, etc. When gasoline and other fuels are stored in drums or tanks, water often enters the storage space, as by breathing, and corrodes the inner surfaces thereof. This can be prevented through the use of the additives contemplated herein.

Relatively more permanent corrosion-preventive coatings can be produced by the application to metal surfaces of paints, and the like, containing the additives of this invention. Vehicles utilizable for this purpose are paints, varnishes, lacquers, drying oils, asphalt roofing compositions, and the like.

The amount of the reaction products which are added to a vehicle to produce a composition in accordance with this invention varies between about 0.001 per cent and about 50 per cent by weight, depending on the specific use contemplated and on the specific reaction products selected. Generally, it is sufficient to use an amount varying between 0.01 per cent and about per cent. However, smaller amounts, as low as about 0.001 per cent, will be effective in some cases. Likewise, amounts up to as much as about 50 per cent are required when the vehicle contains resinous bodies, or when the reaction product is also used as an emulsifier, such as in a steam cylinder oil.

Other substances in addition to the reaction products of this invention can be added to the compositions contemplated herein to impart other desirable properties thereto. For example, there may be added antioxidants, pour point depressants, V. I. improvers, antidetonants, cetane number improvers, emulsifiers, thinners, driers, etc.

Further examples of the preparation of the intermediate products of this invention and of their utility other than as intermediates for producing the antirust agents of this invention are set forth in two copending applications of the present inventors. One application, Serial Number 115,948, filed September 15, 1949, relates to an emulsifiable oil comprising an oil and a small amount of the reaction product of a polyalkylenepolyamine with a monocarboxylic acid containing between about fourteen carbon atoms and about thirty carbon atoms per molecule. The application, Serial Number 122,353, filed October 19, 1949, is concerned with gasolines containing the reaction product of a polyalkylenepolyamine with an aliphatic monocarboxylic acid having between about eight and about thirty carbon atoms per molecule. The reaction produce, per se, is claimed in the latter application.

Although the present invention has been described with preferred embodiments, it is to be understood that-modifications may be resorted to without departing from the spirit and scope thereof, as those skilled in the art will readily understand. Such variations and modifications are considered to be within the purview and scope of the appended claims.

We claim:

1. A corrosion-inhibiting composition which comprises -a substantially neutral vehicle containing between about 0.001 per cent and about 50 per cent by weight of the reaction product obtained by reacting a monocarboxylic acid with a polyalkylenepolyamine having one more nitrogen atom per molecule than there are alkylene groups in the molecule, in a molar proportion varying between about one and about (::-I) to one, respectively, wherein :1: represents the number of nitrogen atoms in the polyalkylenepolyamine molecule, to produce an intermediate product, and reacting an alkenyl succinic acid anhydride with said intermediate product, in a molar proportion varying between about 2-1) and about one to one, respectively; the sum of the number of moles of said monocarboxylic acid and of said alkenyl succinic acid anhydride reacted with each mole of said polyalkylenepolyamine being no greater than 2..

2. The composition of claim 1, wherein said monocarboxylic acid is an aliphatic monocarboxylic acid.

3. The composition of claim 2, wherein said polyalkylenepolyamine is a polyethylenepolyamine having between two and six ethylene groups per molecule.

4. The composition ofv claim 1, wherein said vehicle is an oleaginous vehicle.

5. The composition of claim 1, wherein said vehicle is an aqueous vehicle.

6. The composition of claim 1, wherein said vehicle is a hydrocarbon vehicle.

'7. The composition of claim 1, wherein said vehicle is a mineral lubricating oil.

8. The composition of claim 1, wherein said vehicle is a non-hydrocarbon vehicle.

9. The composition of claim 1, wherein said vehicle is a fatty oil.

10. The reaction product obtained by reacting a monocarboxylic acid with a polyalkylenepolyamine having one more nitrogen atom per molecule than there are alkylene groups in the molecule, in a molar proportion varying between about one and about (ac-1) to one, respectively, wherein :1: represents the number of nitrogen atoms in the polyalkylenepolyamine molecule, to

molecule, in a molar proportion varying betweenabout one and about (:c-2) to one, respectively, wherein :1: represents the number of nitrogen atoms in the polyalkylenepolyamine molecule, to produce an intermediate product, and reacting an alkenyl succinic acid anhydride with said intermediate product, in a molar proportion varying between about (3-2) and about one to one,

. 27 respectively; the sum of the number of moles of said monocarboxylic acid and of said alkenyl succinic acid anhydride reacted with each mole of said polyalkylenepolyamine being no greater than (:c-l).

12. The reaction product obtained by reacting an aliphatic monocarboxylic acid with a polyethylenepolyamine having one more nitrogen atom per molecule than there are ethylene groups in the molecule and having between about two and about six ethylene groups per molecule, in a molar proportion varying between about one and about (ac-1) to one, respectively, wherein :n represents the number of nitrogen atoms in the polyethylenepolyamine molecule, to produce an intermediate'product, and reacting an alkenyl succinic acid anhydride, having between about 8 and about 18 carbon atoms per alkenyl radical,

with said intermediate product, in a molar proportion varying between about (:1:1) and about one to one, respectively; the sum of the number of moles of said aliphatic monocarboxylic acid and of said alkenyl succinic acid anhydride reand about six ethylene groups per molecule, in

a molar proportion varying between about one and about (18-2) to one, respectively, wherein :1: represents the number of nitrogen atoms in the polyethylenepolyamine molecule, to produce an intermediate product, and reacting an alkenyl succinic acid anhydride, having between about 8 and about 18 carbon atoms per alkenyl radical, with said intermediate product, in a molar proportion varying between about (cc-2) and about one to one, respectively; the sum of the number of moles of said aliphatic monocarboxylic acid and of said alkenyl succinic acid anhydride reacted with each mole of said polyethylenepolyamine being no greater than (11-1).

14. The reaction product obtained by reacting an aliphatic monocarboxylic acid with a polyethylenepolyamine having one more nitrogen atom per molecule than there are ethylene groups in the molecule and having between about two and about six ethylene groups per molecule, in a molar proportion varying between about one and about (x1) to one, respectively, wherein a: represents the number of nitrogen atoms in the polyethylenepolyamine molecule, to produce an intermediate product, and reacting an alkenyl succinic acid anhydride having between about ten carbon atoms and about twelve'carbon atoms per alkenyl radical with said intermediate product, in a molar proportion varying between about (x-l) and about one to one, respectively; the sum of the number of moles of said aliphatic monocarboxylic acid and of said alkenyl succinic acid anhydride reacted with each mole of said polyethylenepolyamine being no greater than :11.

15. The reaction product obtained by reacting oleic acid with triethylenetetraminain a molar 28 acted with each mole of said triethylenetetramine being no greater than four. '16. The reaction product obtained by reacting oleic acid with triethylenetetramine, in a molar proportion of aboutone to one, respectively, to produce an intermediate product, and reacting triisobutenyl succinic acid anhydride with said intermediate product, in a molar proportion of about two to one, respectively.

1'7. The reaction product obtained by reacting dodecanoic acid with tetraethylenepentamine, in

per alkenyl radical with said'intermediate prod-' uct, in a molar proportion varying between about four and about one to one respectively; the sum of the number of moles of said dodecanoic acid and of said alkenyl succinic acid anhydride reacted with each mole of said tetraethylenepentamine being no greater than five.

18. The reaction product obtained by reacting dodecanoic acid with tetraethylenepentamine, in a molar proportion of about two to one, respectivel y, to produce an intermediate product, and reacting an alkenyl succinic acid anhydride having between about ten carbon atoms and about twelve carbon atoms per alkenyl radical with said intermediate product, in a molar proportion of about three to one, respectively.

19. The reaction product obtained by reacting oleic acid with triethylenetetramine, in a molar proportion varying between about one and about three to one; respectively, to produce an interproportion varying between about one and about three to one, respectively, to produce an intermediate product, and reacting triisobutenyl succinic acid anhydride with said intermediate product, in a molar proportion varying between about three and about one to one, respectively; the sum in a molar proportion varying between about three and about one to one, respectively; the sum of the number of moles of said oleic acid and of said alkenyl succinic acid anhydride reacted with each mole of said triethylenetetramine being no greater than four.

20. The reaction productobtained by reacting oleic acid with triethylenetetramine, in a molar proportion of about three to one, respectively, to produce an intermediate product, and reacting an alkenyl succinic acid anhydride having between about ten carbon atoms and about twelve carbon atoms per alkenyl radical with said intermediate product, in a molar proportion of about one to one, respectively.

21. A mineral oil'containing between about 0.01 per cent and about 10 per cent by weight of the reaction product obtained by reacting oleic acid with triethylenetetramine, in a molar proportion of about one to one, respectively, to produce an intermediate product, and reacting triisobutenyl succinic acid anhydride with said intermediate product, in a molar proportion of about two to one, respectively.

22. A mineral oil containing between about 0.01, per cent and about 10 per cent by weight of the reaction product obtained by reacting dodecanoic acid with tetraethylenepentamine, in a molar proportion of about two to one, respectively, to produce an intermediate product, and reacting an alkenyl succinic acid anhydride having between about 10 carbon atoms and about 12 carbon atoms per alkenyl radical with said intermediate product, in a molar proportion of about three to one, respectively.

reaction product obtained by reacting oleic acid with triethylenetetramine, in a. molar proportion of about three to one, respectively, to produce 5 in a molar proportion of about one to one, re- 10 spectively.

RALPH V. WHITE. HENRY D. NORRIS. PHIILIP S. LANDIS.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 2,194,419 Chwala. Mar. 19, 1940 2,355,837 Wilson Aug. 15, 1944 2,374,354 Kaplan Apr. 24, 1945 2,473,577 De Groote et a1. June 21, 1949 2,475,409 Smith et a1. July 5, 1949 2,490,744 Trigg et a1 Dec. 6, 1949 2,540,800 Trigg Feb. 6, 1951

Claims (1)

1. A CORROSION-INHIBITING COMPOSITION WHICH COMPRISES A SUBSTANTIALLY NEUTRAL VEHICLE CONTAINING BETWEEN ABOUT 0.001 PER CENT AND ABOUT 50 PER CENT BY WEIGHT OF THE REACTION PRODUCT OBTAINED BY REACTING MONOCARBOXYLIC ACID WITH A POLYALKYLENEPOLYAMINE HAVING ONE MORE NITROGEN ATOM PER MOLECULE THAN THERE ARE ALKYLENE GROUPS IN THE MOLECULE, IN A MOLAR PROPORTION VARYING BETWEEN ABOUT ONE AND ABOUT (X-1) TO ONE, RESPECTIVELY, WHEREIN X REPRESENTS THE NUMBER OF NITROGEN ATOMS IN THE POLYALKYLENEPOLYAMINE MOLECULE, TO PRODUCE AN INTERMEDIATE HYDRIDE WITH SAID INTERMEDIATE SUCCINIC ACID ANHYDRIDE WITH SAID INTERMEDIATE PRODUCT, IN A MOLAR PROPORTION VARYING BETWEEN ABOUT (X-1) AND ABOUT ONE TO ONE, RESPECTIVELY; THE SUM OF THE NUMBER OF MOLES OF SAID MONOCARBOXYLIC ACID AND OF SAID ALKENYL SUCCINIC ACID ANHYDRIDE REACTED WITH EACH MOLE OF SAID POLYALKYLENEPOLYAMINE BEING NO GREATER THAN X.
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