|Publication number||US3034907 A|
|Publication date||May 15, 1962|
|Filing date||Jul 7, 1958|
|Priority date||Jul 11, 1957|
|Also published as||DE1271287B|
|Publication number||US 3034907 A, US 3034907A, US-A-3034907, US3034907 A, US3034907A|
|Inventors||Kleemann Alois, Roggero Rinaldo|
|Original Assignee||Geigy Ag J R|
|Export Citation||BiBTeX, EndNote, RefMan|
|Patent Citations (8), Referenced by (23), Classifications (79)|
|External Links: USPTO, USPTO Assignment, Espacenet|
ilnited States Patent Qfihce 3,634,907 Patented May 15, 1962 3,034,907 ANTI-CORRGSIVE COMPOSITIONS Alois Kleemann, Basel, and Rinaldo Roggero, Riehen, near Basel, Switzerland, assignors to J. R. Geigy A.-G., Basel, Switzerland, a Swiss firm No Drawing. Filed July 7, 1958, Ser. No. 746,599 Claims priority, application Switzerland July 11, 1957 6 laims. (Cl. 106-14) The present invention concerns compositions of matter which are effective agents for hindering or retarding rust formation on iron surfaces and ice formation in the exhaust system of internal combustion engines. It also concerns processes for the production of these agents as well as processes for the prevention or retardation of rust formation on iron surfaces and ice formation in the exhaust systems of internal combustion engines, and also the materials protected by the new compositions of matter.
It is already known that amides of higher alkyl carboxylic acids or alkyl sulphonic acids can be used as anticorrosive agents. It is also known that certain N-polyhydroxyalkylated aliphatic amino compounds have a rustpreventing action. The use of such acid amides or such amines in 'fats and oils, for example as additives to lubricating grease or oil has now also been suggested for the prevention of rust formation on iron surfaces. Many of such compositions of matter however, do not meet practical requirements; either the active ingredients have a detrimental effect on the properties of the carriers or the effect is too slight in economically practical concentrations in these carriers.
It has now been found that compositions of matter made up from N-carboxyalkylamides of higher molecular carboxylic acids and certain hydroxyalkylated amines or nitrogen bases in oily carriers have a strong water-removing action on metal surfaces treated therewith and in particular, have a rust preventing or retarding action on iron surfaces which exceeds the sum of the actions to be expected from the individual components. Because of their strong water-displacing properties on metal surfaces, the compositions of matter are also effective agents against stalling due to carburettor icing in internal combustion engines under extreme climatic conditions.
The present invention concerns compositions of matter which are characterized by a content of (a) a hydro phobic organic carrier, (b) a carboxylic acid amide monocarboxylic acid of the general Formula I Rr-C OIYT-R3C O OH R2 7 V (I) and (c) an at least equivalent amount of a hydroxyalkylated nitrogen base which contains at least one lipophilic radical.
In the general Formula I R represents a lipophilic group or an organic radical containing at least one lipophilic group,
R represents hydrogen or a lower alkyl group, and
R represents a lower alkylene group, in particular a methylene group.
The compounds of the general Formula I are functional derivatives of natural or synthetic amino acids and higher molecular carboxylic acids having lipophilic groups. By lipophilic groups are meant chiefly saturated and unsaturated, aliphatic or also alicyclic hydrocarbon radicals having straight or branched chains and 4 to 40 carbon atoms. Also halogenated aliphatic radicals, in particular alkyl radicals perfluorated in the end position can be used. If only one lipophilic hydrocarbon radical is present, then it has at least 8 and advantageously 12 to 18 carbon atoms. If more aliphatic and/ or alicyclic radicals are present, then together they have at least carbon atoms. In
this case, a single lipophilic radical should have at least 4 carbon atoms. When alkyl radicals perfluorated in the end position have a low number of carbon atoms, for example if they contain only 5 carbon atoms, they are already lipophilic. Derivatives of aliphatic monocarboxylic acidshaving at least 10 carbon atoms are used advantageously according to the present invention as amide derivatives of the general Formula I. Examples are the derivatives of lauric, myristic, palmitic, stearic or higher fatty acids, then those of unsaturated higher carboxylic acids such as undecylenic acid, oleic acid and elaidic acid, ricinoleic acid, erucic and linoleic acid. Naturally also the acid amide derivatives from mixtures of carboxylic acids such as are found in nature as esters of monovalent alcohols in waxes or as glycerides in fats and oils or which are contained in the so-called Fischer-Tropsch tail fraction acids can be used. In addition, amide derivatives of those carboxylic acids can be used in which aliphatic hydrocarbon chains are interrupted by bridge-forming groups such as, for example, oxygen or sulphur ether groups or by aromatic radicals. Examples are the derivatives of decyl-, dodecyl-, hexadecyl-, octadecyloxy acetic acids and thioacetic acids, also derivatives of a-heptyland )3- octyloxy propionic acids, of u-butoxylauric acid, of octyl and nonyl phenoxy acetic acids and phenyl stearic acid.
The amide derivatives of compounds of the general Formula I used according to the present invention are derived from aliphatic aminocarboxylic acids. Advantageously the compounds contain the radicals of low molecular amino acids such as, for example, those of glycin, alanine, valine and leucin and, in particular, those of the N-alkyl derivatives of these amino acids. Compounds containing the radical of sarcosine such as, for example, oleyl sarcoside, are particularly effective in the compositions of matter according to the present invention'and are, therefore, preferred. The acylamino fatty acids of the general Formula I are obtained from the low molecular amino fatty acids by reacting with fatty acid chlorides containing lipophilic radicals and, possibly, also aromatic radicals.
Hydroxyalkylated nitrogen bases which contain at least one lipophilic radical and at least one hydroxyalkyl group are used in the compositions of matter according to the present invention as amine component. The lipophilic radical can be aliphatic, normal or branch chained, saturated or partly unsaturated or it can be alicyclic, sat urated or partly unsaturated. Advantageously a single lipophilic radical contains at least 10 carbon atoms and several lipophilic radicals together also contain at least 10 carbon atoms, an individual radical containing at least 4 carbon atoms. The lipophilic radicals can be bound to the basic nitrogen atom either direct or by way of bridging members. Divalent hydroxyalkyl, thioalkyl, aminoalkyl and, in particular, also carbonyl hydroxyalkyl groups are used as bridging members. The cyclohexyl radical and homologues thereof, petroleum hydrocarbon radicals containing cyclopentyl radicals, the abietyl and dihydroabietyl radical are examples of alicyclic lipophilic radicals. Advantageously however, straight chained alkyl groups with more than 10 carbon atoms form the lipophilic radical of the nitrogen bases used according to the present invention, for example the lauryl, cetyl, oleyl or stearyl radical. The hydroxyalkyl group of the nitrogen base is advantageously low molecular and contains 2 to 6 carbon atoms and 1-3 hydroxyl groups. 7 Examples are the Z-hydroxyethyl, Z-hydroxypropy-l, 2,3-dihydroxypropyl and the trihydroxy-tert. butyl groups. A great num: ber of hydrophilic groups should not be present however. lntrihydroxy-tert. butylamine bases, therefore, advantageously at least one hydroxy group is esterified with a higher fatty acid or an alkoxy fatty acid. Because of their easier technical accessibility and their good action, reaction products from primary and secondary aliphatic monoand poly-amines containing lipophilic radicals and aliphatic or araliphatic epoxides such as propylene oxide, styrene oxide and, in particular, ethylene oxide, are preferred. Examples are stearyl-diethanolamine, oleyl diethanolamine, N hydroxyethyl N stearyl-ethylene diamine, N'-hydroxyethyl-N-oleyl-ethylene diamine, N"- hydroxyethyl-N-stearyl-diethylene triamine, N"-hydroxyethyl N oleyl-diethylene triamine, N.N.N-trihydroxyethyl-N-stearyl-ethylene diamine. Apart from these preferred amine components however, also other amines as defined such as, for example, triethanolamine dilauric acid ester, dimethyl-trihydroxy-tert. butylamine monoor dioleic acid ester, oleyl diethanolamine-mono-decyl thioacetic acid ester, oleyl diethanolamine-mono-decyloxy acetic acid ester, stearyl diethanolamine-lauroyl sarcosine monoester, oleyl diethanolamine-oleyl sarcosine monoester and other similar compounds produce compositions of matter according to the present invention which are very effective.
Carboxylic acid amide-monocarboxylic acids of the general Formula I and hydroxyalkylated amines having a lipophilic radical can be used in various proportions in the compositions of matter according to the present invention. In general, almost equimolecular or stoichiometric amounts are used. Sometimes so much hydroxyalkylated amines are used that complete salt formation with the carboxylic acid amide monocarboxylic acid occurs and an excess serves as solvent. Advantageously the carboxylic acids are used as such, but they can also be used in the form of their metal salts or salts of organic bases, both of which are soluble in oil.
Compositions of matter according to the present invention contain hydrophobic organic compounds as carriers for the water displacing and rust preventing active substances, ie those substances which are insoluble in Water. Such hydrophobic carriers are the natural and synthetic, solid and liquid and, of these, chiefly the saturated hydrocarbons, and also waxes, fats and oils as well as resins, lacquers, varnishes. The choice of carrier as well as the content of active ingredient is determined by the intended use. The content of active substances depends also possibly on their solubilities in the carriers chosen. The content of active substances in the compositions of matter can vary within wide margins. Generally slight amounts are sufiicient; as anti-corrosive agent for example as low as 0.001, but generally 0.1 to 5% calculated on the weight of the hydrophobic carrier and, to prevent icing in the exhaust system of internal combustion engines for example to 200 parts per million parts of power fuel.
F or the protection of iron surfaces against rust, for example mineral or synthetic lubricating oils, lubricating greases, hydraulic oils, compressor oils, turbine oils, soluble oils, grinding oils and cutting oils can be used as hydrophobic carriers in the compositions of matter according to the present invention. In order to obtain anti-corrosive agents which can easily be smeared, sprayed or dusted, the oily carriers mentioned above can be combined with more easily volatile diluents and with propellants. The anti-corrosive agents according to the present invention can be used for the protection of clean iron parts of storage vessels, pipes, turbines, motors, firearms and other machines or parts thereof. The anti-corrosive agents according to the present invention are also very well suited for the temporary protection of iron stored in a half finished state.
Another possible use is in the wide field of paints for the temporary and permanent protection of metal surfaces. For this purpose, the new anti-corrosive agents can be mixed, for example with linseed oil colours, synthetic resin emulsions, lacquers, silicone oils and under coatings. For the temporary protection of the surfaces of iron materials they are used for example in petroleum or fats and, in particular, in mineral oils.
The active substances used in the compositions of matter according to the present invention generally have no injurious eifect on the hydrophobic carriers. In the same way, when used in lubricating oils, paints, combustion oils etc., they have practically no injurious eifect on the properties of these agents. They are also compatible with the usual oil additives such as antioxidants, metal deactivators, anti-frothing agents, surface active agents, dispersion promoters, viscosity improvers or dyestufis and can be used therefore with such additives. Some of the new compositions of matter according to the present invention are valuable anti-corrosive agents on metals other than lI'OIl.
Because of their strong Water displacing action, the compositions of matter according to the present invention are suitable for the rust protective treatment of the under side of motor vehicles or for the drying and temporary storage of iron tools which, when being worked upon, have been cooled with water. To this same property is due their activity against icing of carburettors in internal combustion engines which often occurs under damp or cold atmospheric conditions when using volatile fuel following a period of light load operation. The icing causes blocking of the throttle valve and the engine stalls. Very slight additions of for example 20 to 200 parts per million of the components (b) and (c) to volatile fuels (50% ASTM [American Society for Testing Materials] distillation point for example less than C.) hinders the icing. In this connection it is of particular importance that the other usual fuel additives are neither unfavorably influenced nor is the cylinder or the exhaust system partially blocked by undesired deposits.
Anti-corrosive agents according to the present invention therefore consist of an oily carrier, for example a synthetic and, advantageously, a mineral lubricating oil or a lubricating grease, and 0.1 to 5% calculated on the weight of the oily carrier of a composition of matter consisting of an acylamino fatty acid of the general Formula I werein R is a lipophilic radical from the classes of aliphatic hydrocarbon radicals with 12 to 30 carbon atoms, of alkoxy methylene radicals and alkyl thiomethylene radicals with 12 to 30 carbon atoms, and of alkyl phenoxy methylene radicals with alkyl substituents totalling at least 8 carbon atoms, the first class being preferred because of easier technical accessibility and good influence on the activity of the composition of matter; wherein R is hydrogen, or a low molecular alkyl group and R is a lower alkylene group, preferably the methylene group; and of at least the equivalent amount of a hydroxyalkylated nitrogen base which contains one or more lipophilic radicals from the class of aliphatic, araliphatic and alicyclic hydrocarbon radicals each having at least '5 and in all at most 10 saturated carbon atoms and the hydroxyalkyl groups of which consist of 2 to 4 carbon atoms and contain in all 1 to 3 free hydroxyl groups. This hydroxyalkylated nitrogen base corresponds to the general Formula II B2 (II) wherein L represents a lipophilic radical defined above,
X represents a bridging member which is bound to the nitrogen atom by means of an aliphatic carbon atom and which is selected from the group of lower-0- alkylene, -S-alkylene-, -O-hydroxyalkylene, -S-hydroxyalkylene,
alkylene (R'=H, low molecular alkyl or low molecular hydroxyalkyl), -CO-O-alkylene and -CO-O-hydroxyalkylene radicals,
n. represents the integer or 1,
R represents hydrogen, a lower alkyl or lower hydroxyalkyl or lower aminoalkyl radical, and
R is the same as (LX and R the condition being that of the radicals X, R and R at least one is a low molecular, hydroxyalkylated aliphatic radical. In a preferred form, L represents an aliphatic hydrocarbon radical with 12 to 18 carbon atoms, n is 0 and at least one of R and R is a low molecular hydroxyalkyl or hydroxyalkylarninoethyl radical.
The fuel mixtures according to the present invention contain as predoninant part a hydrocarbon mixture of benzene of 50% ASTM distillation point under 115 and 10 to 200 parts per million, advantageously 20 to 100 parts per million of an antistalling adjuvant consisting of an acylamino fatty acid of the general Formula I with the same definition of the substituents as is given in the preceding paragraph for the anti-corrosive agent and of at least an equivalent amount of a hydroxyalkylated nitrogen base with a lipohilic radical as defined in the preceding paragraph. In this case too, the lipophilic radical is an alkyl or alkenyl radical containing 12 to 18 carbon atoms, the hydroxyalkyl group is advantageously a 2-hydroxyethyl group and the nitrogen base is advantageously an aliphatic monoor poly-amine, in the latter case, advantageously an ethylene -arnine where n is l to 3 and advantageously 1. Naturally the fuel mixtures according to the present invention can contain other usual additives.
Further details can be seen regarding the new anticorrosive and anti-stalling agents from the following examples. In particular methods are also described in the examples by which the activity of the agents has been tested and the results are given. The examples do not limit the invention in any way. The temperatures are in degrees centigrade and, where not otherwise stated, parts are given as parts by weight. The relationship of parts by weight to parts by volume is as that of grammes to cubic centimetres.
Example 1 20 parts of oleoyl sarcoside and of N-(hydroxyethylamiuoethyl)-stearylamine of the formula are dissolved in 750 parts of spindle oil of 1-2 Engler degrees (50 measured). parts of fenchyl alcohol, to improve the smell, 20 parts of micro'ceresin, to modify the oil film, as well as 20 parts of morpholine and 165 parts of distilled petroleum, as solvent, are added to the mixture. A thinly liquid anti-corrosive oil which can be painted well is obtained.
If plain sheet iron is painted with this anti-corrosive agent and exposed to a damp atmosphere, no rust formation can be seen after 4. weeks whilst rust is clearly visible on sheet iron treated with oil alone even after 3-4 days.
If in the above composition of matter, 17 parts of an addition product of 1 mol of ethylene oxide and 1 mol of a fatty amine mixture derived from coconut fatty acid, or 21 parts of the compound of the formula are used instead of the N-(hydroxyethyl-aminoethyl)- stearylamine, then oils having similar properties are obtained.
Example 2 25 parts of stearoyl sarcoside and 25 parts of N-bis- (hydroxyethyl)-stearylamine are rubbed with 5 parts of terpin into a homogeneous mass. The thickly. liquid mixture is then dissolved at room temperature in 945 parts of mineral oil SAE 40 (-12 Engler degrees at 50).
This composition of matter is suitable for example for the treatment of weapons, tools, machines or power-propelled vehicles to prevent the iron parts thereof from the formation of rust or at least to strongly hinder such formation.
If 20 parts of the compound of the formula:
COOH CB5 or 18 parts of lauroyl sarcoside are used instead of the stearoyl sarcoside, then anti-corrosive oils having similar properties are obtained.
If in the above composition of matter a transmission lubricant SAE of 25-30 Engler degrees at 50 is used instead of the mineral oil, then a rust-preventing lubricant oil for gears and bearings which has a remarkable hydrophobic action is obtained.
Example 3 A mixture of 25 parts of oleoyl sarcoside and 25 parts of N-bis-(hydroxyethyl)-stearylamine is dissolved at room temperature in 760 parts of spindle oil of a viscosity of 1-2' Engler degrees (measured at 50"). 5. partsof fenchyl alcohol, 20 parts of ceresin, (20 parts of dioxan and '145 parts ofdistilled petroleum are added to the solution. An excellent anti-corrosive oil is obtained which can be sprayed Well both from an ordinary spray and from an atomiser. When used as a grease, the film adheres well to the metal surface. Lacquers, synthetic materials and rubber are not noticeably; affectedby the oil.
To test the rust-preventing properties of this oil, both sides of plain iron sheets are coated with this oil (D) and sprayed at room temperature alternately with distilled and withordinary tap water in a so-called fog spray chamber. As a comparison, three other series of iron sheets are tested. One series (C) consists of iron sheets which are coated with a mixture of spindle oil, fenchyl alcohol, ceresin, dioxan and petroleum (of the same qualities and amounts as in the above composition of matter) and 5% by weight of oleoyl sarcoside. Series B are coated with a mixture which contains 5% by weight of N-(dihydroxyethyl)-stearylamine instead of oleoyl .sarcoside, and series A is coated with'an oil mixture not containing an anti-corrosive agent. The results are as follows: 1
Series A shows clear rust formation after 10 hours exposure to fog spray, Series B shows clear rust posure to fog spray, Series C shows clear rust formation after 11-0 hours exposure to fog spray, Series D showed no rust formation after more than 500 hours exposure.
formation after 40 hoursex- 7 Example 4 20 parts of decyloxyacetyl sarcoside of the formula owmro-om-oo-N ortkooon i on, V
and 30 parts of N.N.N'-tris-( hydroxyethyl)-aminoethyl- 'stearylamine of the formula:
stirring in order to attain aclear solution. After cooling, an excellent, vsoft anti-corrosive grease is obtained which can be used for example for instruments and tools.
No rust formation can be determined on plain iron partsor the same number of parts of the decyloxyacetyl glycide of the formula C H OCH CONHCH COOH are used, then a grease having similar properties is obtained.
Example 4.5 parts of oleoyl sarcoside and of N-(p-hydroxy-aphenylethyl)-stearylamine of the formula:
and 1.0 part of fenchyl alcohol are thoroughly mixed together. 500 parts of ozocerite (white), 300 parts of montan wax, 100 parts of carnauba wax and 90 parts of lanolin are added to this mixture. The whole is heated for a short time at 80-90 and, after cooling, a homogeneous mixture is obtained. The fusion point of this wax is 60-70. On applying to plain and chromed iron parts of vehicles and then polishing for example, an excellent anti-corrosive coating is obtained. On dipping cold objects for a short time into the wax which has been made liquid by warming to about 90", a protective film having a very good anti-corrosive action is obtained on the objects.
It in the above composition of matter, instead of the N-(fl-hydroXy-a-phenylethyl)-stearylamine, 4 parts of N- (hydroxyethylaminoethyl)-stearylamine of the formula C H -;NH-CH CH NHCH -CH OH or 4 parts of the compound of the formula are used, then waxes having similar properties are obtained.
Example 6 2 parts of oleyl sarcoside, 2.4 parts of dimethylarninotrimethylolmethane oleic acid monoester and 3 parts of microcrystalline wax are dissolved while warming in a mixture of 4 parts of dioxane and 90 parts of diesel fuel oil. A relatively thinly liquid anti-corrosive oil which can be sprayed and painted is obtained.
To test the protective action of this oil, iron plates which have been brushed completely clean (steel with 0.08% C) are dipped in this oil and are hung up for one day to allow excess oil to run off.
The whole plates are then dipped in distilled water and stored for a week. After this time, the plates are completely clean and have no sign of crust formation whilst plates treated as a comparison with diesel fuel oil and wax were covered to an extent of 90% with rust.
Example 7 2 parts of dimethylaminotrimethylolmethane oleic acid diester, 1 part of stearoyl sarcoside, 2 parts of microceresin, 2 parts of dioxan and 0.5 part of fenchyl alcohol are dissolved while warming to about 50 in 92 parts of mineral oil of 10-12 Engler degrees (measured at 50). An opalescent anti-corrosive oil is obtained.
Iron sheets brushed clean are painted with this anticorrosive oil and their stability to corrosion is tested by storing them in a corrosion chamber. The mist in the Example 8 3 parts of triethanolamine dilauric acid ester, 2 parts of oleyl sarcoside, 5 parts of fenchyl alcohol, 20 parts of ceresin, 50 parts of palm nut oil and 20 parts of mineral oil are melted into a homogenous mass while stirring at about After cooling, a soft anti-corrosive grease which can be smeared on is obtained. It can be used, for example for instruments or firearms.
If this anti-corrosive grease is rubbed with a cloth onto exposed steel fittings and the fittings are kept in an atmosphere saturated with steam, no rust formation can be seen for more than 1 month.
Example 9 2 parts of dihydroxyethyl oleylamine decylthioacetic acid monoester, 1 part of oleyl sarcoside and 2 parts of dioxan are dissolved in parts of a mineral oil of a viscosity of Saybolt Universal seconds (38) refined by extraction. An anti-corrosive oil which can easily be sprayed or smeared is obtained. If steel sheets (0.08% C) are brushed clean and sprayed with this anti-corrosive oil and then kept in an atmosphere saturated with steam, after 30 days they are completely shining and free from all traces of rust whilst control sheets which have only been sprayed with the mineral oil mentioned without additives, are covered with a layer of rust after this time under the same conditions.
If in the above composition of matter, instead of the dihydroxyethyl oleylamine decylthioacetic acid monoester the same amount of dihydroxyethyl oleylamine decylhydroxyacetic acid monoester is used, then a thinly liquid anti-corrosive oil having similar properties is obtained.
Example 10 2 parts of dihydroxyethylstearylamine lauroyl sarcosine monoester, 1 part of oleyl sarcoside, 2 parts of dioxan and 0.5 part of fenchyl alcohol and 2 parts of microceresin are dissolved in 92.5 parts of a petroleum distillate (boiling range 150-210, flash point over 35). If pieces of iron which, while being worked upon are cooled by spraying with water, are dipped into the composition of matter described above immediately afterwards then the water is removed from the surface of the metal within a few seconds. On being stored in a damp, corrosive atmosphere, pieces of iron dried in the manner described are remarkably stable to rust.
If in the composition of matter named the dihydroxyethylstearylamine lauroyl sarcosine monoester is replaced by the same amount of dihydroxyethyl oleylamine oleyl sarcosine monoester then a water removing anti-corrosive preparation having similar activity is obtained.
Example 11 Six fuel mixtures are prepared as follows: equal parts of first oleoyl sarcoside and then octadecyl diethanolamine are dissolved in a fuel for internal combustion engines containing petroleum distillates and reformed hydrocarbons, the 50% ASTM distillation point of which fuel is 90. The six fuels are made up in the ratio of 0, 10, 20, 30, 40 and 50 parts of additives to one million parts of fuel. The anti-icing action was tested as follows:
A 1 cylinder motor with a Solex carburettor was run with the fuels prepared in laboratory tests under the following test conditions and the time was measured in minutes until the motor stalled due to blocking of the carburettor.
The air supply was passed through a humidifier (Standard Model CFR, described in ASTM Manual for Rating Fuel by Motor and Research Methods 1956) and onJa ass st;
- e v s r the fuel was cooled to by surrounding the feed pipe with ice. The carburettor was also built into a cooling chamber which was kept at 0 by intensive ice cooling. The engine was run at a fixed throttle opening for all tests and the reduction of speed and eventual stalling of the engine due to ice formation in the carburettor was observed. v
The tests were run under the following conditions:
B.P. at end of distillation 195 A fuel was regarded as meeting all practical requirements when the engine did not stall within 60 minutes.
The results of the fuel tests can be seen from the following table:
Running Percent im- Parts of additive per million minutes provement until stalling of running time n 15% 10 22 42 an 283 84 30 35% 129 0 43 177 50 60 287 The fuel thus meets all practical requirements when it contains 50 parts of additives per million.
In the same manner the combinations from acylamino fatty acids and hydroxyalkylated amines described in Examples 1 to 10 can be used as additives to motor fuels.
In addition to the compounds listed in the examples, also the following amine components for example can be used in the compositions of matter according to the present invention:
(1) 3 nonylphenoxy 2 hydroxypropyl-dimethyl and -diethyl amine,
(2) 3 nonylphenoxy 2 hydroxypropyl-monoethanolamine,
(3) 3 nonylphenoxy 2 hydroxy propyl-2-hydroxypropylamine,
(5) 3-(2.4'-di-tert. amylphenoxy)-2 hydroxypropylmonoethanolamine,
(6) 3-(2.4'-di-tert. amylphenoxy) 2 hydroxypropyl- 2-hydroxypropylamine,
(7) 3-(2'.4-di-tert. amylphenoxy) 2 hydroxypropyldiethanolamine,
(8) 3-hexadecylmercapto 2 hydroxypropyl-dimethylamine,
(9) 3 hexadecylmercapto 2 hydroxypropyl monoethanolamine,
(10) 3-hexadecylmercapt0 2-hydroxypropyl-2'-hydroxypropylamine.
(11) 3-octadecylmercapto-2-hydroxypropyl dimethylamine,
(12) 3 octadecylmercapto 2 hydroxypropyl monoethanolamine,
(13) 3 octadecylmercapto 2' hydroxypropylamine (produced from the corresponding alkali metal phenolates or mercaptides in inert organic solvents such as hydrocarbons or chlorinated hydrocarbons with epichlorohydrin and reacting the 2.3-epoxypropyl-(1)-ethers or thioethers obtained with the corresponding amines or with NH and reacting the primary amines obtained with l or 2 mols of ethylene oxide or propylene oxide),
I (14) N dodecylbenzyl N dihydroxyethyl ethylene diamine,
p (15) N-dodecylbenzyl N hydroxyethyl-ethylene, diamine (produced. by reacting the corresponding amines with dodecylbenzylamine) I (16) dodecylbenzyl-diethanolamine,
( 17) dodecylbenzyl-di- (2-hydroxypropyl) -amine (produced from i i NHB dodecylbenzyl chloride dodecylbenzylamlne plus 2 mols of ethylene oxide or propylene oxide),
( l8) N-dicyclohexyl-ethanolamine,
' (19) N-dicyelohexyl-2-hydroxyproy1amine (produced from dicyclohexylamine+ethylene oxide or 1.2-propylene oxide),
(20) Dehydroabietylmonoand -diethanolamine,
(21) Dehydroabietyl-monoand di-2-hydroxY-propylamine (produced from dehydroabietylamine by reacting with ethylene oxide or propylene oxide),
' (23) Octadecylhydroxyethyl-monoethanolamine,
(25) Dodecylmercaptoethyl monopropanolamine,
(28) 1 dodecylphenoxypropyl (2) monopropanolamine (produced from the corresponding higher molecular alcohols, mercaptans or phenols by reacting with 1 mol of ethylene oxide or propylene oxide to form the corresponding hydroxyalkyl ethers, sulphating these, for example with chlorosulphonic acid in the cold and reacting the acid sulphuric acid esters with excess ammonia or direct with primary or secondary alkanolamines, the primary amine produced with ammonia being then reacted with 1 to 2 equivalents of ethylene oxide or propylene oxide).
All these compounds are oily to wax-like masses.
What we claim is:
1. An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties, said composition consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of an acylamino fatty acid selected from the group consisting of oleoyl sarcoside and stearoyl sarcoside, and of a hydroxy alkylated nitrogen base selected from the group consisting of stearyl diethanolamine, dihydroxyethyl oleylamine decylthioacetic acid monoester, dihydroxyethyl stearylamine lauroyl sarcosine monoester, dimethylaminotrihydroxy methyl methane oleic acid monoester, N.N'.N-trihydroxyethyl-N-stearyl-ethylene diamine and dihydroxyethyl oleylamine oleyl sat-cosine monester, the ratio of parts by weight of said 'acylamino fatty acid in said mixture to said hydroxyalkylated nitrogen base being substantially between 0.5 :1 to 1.5 1.
2. An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties, said composition consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of oleoyl sarcoside and of stearyl diethanolamine, the ratio of parts by weight of said oleoyl sarcosi-de to stearyl diethanolamine in said mixture being substantially between 0.5:1 to 15:1.
3. An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties, said composition consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of stearoyl sarcoside and of stearyl diethanolamine, the ratio of parts by weight of said stearoyl sarcoside to stearyl diethanolamine in said mixture being substantially between 0.5:1 to 1.5 :1.
4. An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties, ,said composition consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of oleoyl sarcoside and o f dihydroxyethyl oleylamine decylthioacetic acid monoester, the rationof parts by weight of said oleoyl sarcoside to dihydroxyethyl oleylamine decylthioacetic acid monoester in said mixture being substantially between 0.5 :1 to 1.5 :1.
5. An anti-corrosive composition of matter which on ferrous surfaces contacted therewith exhibits water displacing and rust preventing properties, said composition consisting essentially of (a) mineral oil and (b) from 0.001 to 5% relative to the weight of said oil of a mixture consisting of oleoyl sarcoside and of dihydroxyethyl stearylamine lauroyl sarcosine monoester, the ratio of parts by weight of said oleoyl sarcoside to dihydroxyethyl stearylamine lauroyl sarcosine monoester in said mixture being substantially between 0.5:1 to 1.5 :1.
6. An anti-corrosive composition of matter which on References Cited inthe file of this patent UNITED STATES PATENTS 2,403,067 Fischer et a1. July 2, 1946 2,706,677 Duncan et al. Apr. 19, 1955 2,790,779 Spivack et a1. Apr. 30, 1957 2,843,464 Gaston et a1. July 15, 1958 2,856,363 Brennan Oct. 14, 1958 2,872,303 Donlan Feb. 3, 1959 2,902,354 Gi-ammaria. Sept. 1, 1959 2,919,979 Martin et a]. Jan. 5, 1960
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|U.S. Classification||106/14.31, 252/392, 44/406, 508/500, 44/433, 252/391, 422/7, 106/14.29|
|International Classification||C23F11/14, C10L1/24, C10L1/14, C10L1/22, C10M141/08, C23F11/10, C10M133/02, C23F11/16|
|Cooperative Classification||C10M2215/225, C10M2207/40, C10M2215/22, C10M2203/108, C10L1/14, C10M2215/082, C10M2215/30, C10M2203/04, C10N2240/042, C10M2215/04, C10N2230/12, C23F11/145, C10M2215/221, C10M2215/00, C10M141/08, C10M2215/28, C10M2207/404, C10M2215/122, C10M2203/02, C10M2215/086, C10M2205/14, C10N2250/10, C10M2215/08, C10N2240/108, C10M2215/042, C10M2205/16, C10M2203/024, C10M2203/10, C10M2217/06, C10M2219/082, C10M2203/022, C10N2240/046, C10N2240/04, C10M2219/084, C10M2219/06, C10L1/2418, C23F11/16, C10M2203/102, C10M2217/046, C10M2203/106, C10M2207/021, C10N2240/14, C10M2215/12, C10N2240/401, C10M2219/085, C10L1/2225, C10M2203/104, C10M2205/17, C10N2240/08, C23F11/10, C10M2215/226, C10N2240/044, C10M2207/044, C10L1/224, C10M2207/02, C10M2215/26, C10M133/02|
|European Classification||C10L1/14, C23F11/10, C10M133/02, C10M141/08, C23F11/16, C23F11/14C|