US3317427A - Cyclohexane-dicarboxylic imide type functional fluids - Google Patents

Cyclohexane-dicarboxylic imide type functional fluids Download PDF

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US3317427A
US3317427A US454678A US45467865A US3317427A US 3317427 A US3317427 A US 3317427A US 454678 A US454678 A US 454678A US 45467865 A US45467865 A US 45467865A US 3317427 A US3317427 A US 3317427A
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Prior art keywords
imide
imides
cyclohexane
alkyl
cis
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US454678A
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Dazzi Joachim
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Novartis Corp
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Geigy Chemical Corp
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Definitions

  • the present invention concerns the use of imides which are liquid under the conditions for use as functional fluids, as well as compositions of matter which contain the imides usable according to the invention and other usual functional fluids and, optionally, additives which improve or modify their properties.
  • lubricant fluid for machines a fluid without the presence of which a machine cannot perform its function.
  • Lubricants, hydraulic fluids, damping and brake fluids, dielectric fluids, heat-transferring agents, for example, are included in this term (cf. Roger E. Hatton, Introduction to Hydraulic Fluids, Reinhold Publishing Corporation, New York, 1962, -p. 5
  • High boiling organic esters such as diesters of dicarboxylic acids, e.g. adipic or sebacic acid, with alcohols having medium to long carbon chains, also triesters of trimethylol propane and higher fatty acids or esters of wherein each of R and R" represents hydrogen or, together they represent a lower alkylene group having 1 or 2 carbon atoms, a preferred subclass of compounds being that in which R and R" together represent the methylene group, and R represents an alkyl group having 6 to 18, and still more preferably 8 to 12 carbon atoms in a straight chain, have particularly advantageous properties as functional fluids, i.e. their properties represent a highly suitable compromise of the required properties mentioned hereinbefore.
  • N-alkyl imides as lubricants
  • cyclic N-alkyl imides as lubricants
  • N-alkyl succinimides having long chained substituents
  • such N-alkyl succinimides the alkyl radical of which has 8 to 12 carbon atoms
  • N-alkyl imides used according to the invention particularly those the alkyl radical R of which has 8 to 12 carbon atoms, are fluids which, in the pure state, melt by at least 40 C. lower than the N-alkyl succinimides having identical nitrogen substituents.
  • N-alkyl imides usable according to the invention such as are formed when produced from technically obtainable primary amines, often solidify only at 60 C.
  • N-alkyl imides according to the invention can also be used under arctic or stratospheric conditions.
  • the N-alkyl imides according to the invention have considerably better stability to oxidation than the previously known N-alkyl succinimides. Thanks to this property, they can also be used at higher temperatures as lubricants, at which temperatures the previously known succinimides are insuflicient.
  • Another advantage of the N-alkyl imides used according to the invention over the previously known N-alkyl succinimides is that, with identical N-substitution, they are considerably less volatile.
  • the imides used according to the invention are colorless to pale yellowish fluid oils of decreasing consistency at room temperature.
  • the N-alkyl imides used according to the invention are distinguished by particularly good stability to heat with, at the same time, good lower temperature properties. For instance, they decompose only at over 3 C. whilst the organic esters which up to now have been the most stable to heat, e.g. the triesters of fatty acids with trimethylol propane, are unusable even above 360 C.
  • Another advantage of the N-alkyl imides over lubricants based on organic and also inorganic esters is that, in contrast to the esters, they form almost no acid decomposition products on thermal decomposition.
  • Another advantage of the imides according to the invention compared with lubricants based on alkyl esters of organic acids, on phosphoric acid esters, alkyl silicons and silicates, consists in that they are more stable to the influence of 'y-rays.
  • the alkyl imides of Formula I used according to the invention surpass the lubricants based on organic esters in that they do not swell certain plastics used for the production of gasket materials unduly.
  • the imides according to the invention are distinguished by a better lubricating effect and also, moreover, compared with the polyphenyl ethers, also by a lower solidifying point, a viscosity which is less dependent on temperature and a lower density.
  • the imides of Formula I used according to the invention are suitable for the lubrication of the most various surfaces; for instance, they considerably reduce the friction of metal on metal and also, that of metal on silicates such as glass.
  • An advantage of the imides used according to the invention is their surprisingly good miscibility with other usual functional fluids, for example with those based on organic esters, polyaryl ethers, polyalkyl melamines, high boiling phosphoric acid esters, high boiling mineral oils, certain silicone oils or orthosilicates.
  • This favorable miscibility makes the production of special lubricants possible in that the properties required for a certain use but which cannot be attained by the individual components, can be obtained by the production of suitable mixtures.
  • a further advantage of the imides usable according to the invention consists in their relatively high dielectric constant so that they can be used as dielectrics. In addition, they are non-toxic under practical conditions (oral DL in the mouse: 5000' mg./kg.).
  • Mixtures as defined of imides of Formula I are particularly suitable as functional fluids, preferably those mixtures in which the number of compounds in which R is a hexyl group is less than the sum of the number of compounds in which R is an octyl, decyl or dodecyl radical, is at least 95% and the number of compounds in which R is an alkyl radical higher than the dodecyl radical, is less than 5%; these proportions are percentages by weight calculated on the total weight of the mixture. Such mixtures are the most advantageous compromise between low solidification point and slight volatility. Also, imides of Formula I wherein R and R" are hydrogen are preferred for reasons of economy.
  • antioxidants in order to hinder the auto-oxidation which sets in above this temperature.
  • the amount of antioxidant is about 0.01 to 5% by weight of the total weight of the lubricant or functional fluid.
  • antioxidants there are usable secondary monoamines, particularly diarylamines having carbocyclic or heterocyclic radicals as well as aromatic diamines the amine substituents, preferably secondary, of which are in the ortho or, advantageously, the para-positions.
  • carbocyclic and heterocyclic aromatic diaryl amines which can be used as antioxidants are diphenylamines, phenylnaphthylamines, phenylacenaphthenylamines; .4,4-dinaphthylaminodiphenyl; thiazolyl- (2)-naphthylamines; examples of aromatic diamines are N,N-diphenyl-p-phenylenediamine, N,N-dioctyl-p-phenylenediamine, N,N-dicyclohexyl-p-phenylenediamine, N- sec. butyl-N'-phenyl-p-phenylenediamine, N,N'-bis-('yaminopropyl -p-phenylenediamine.
  • Hydroxyl-substituted aromates can be employed as antioxidants particularly at not too high temperatures (i.e under ZOO-300 C. depending on type of the lubricant and substratum), are especially phenols or naphthols having a sterically hindered hydroxyl group as well as the derivatives of dihydroxyaryl compound the hydroxyl groups of which are in 0- or p-position to each other.
  • Examples of particularly valuable compounds which can be used are the monophenol derivatives such as 2,4-dirnethyl-6-tert.butylphenol, 2,6-di-tert.butyl-4-ethylphenol, 2,6-bis-(1-methylcyclohexyl)-4methylphenol, 2,6-di-tert.butyl-4-dimethyl-aminomethyl phenol, 2,2-methylene-bis-(4-methyl-6-tert.butyl phenol), 2,2'-thi0-bis- (4-methyl-6-tert.butylphenol) 4,4'-dihydroxy-2,2-dimethyl-5,5-di-tert.butyldiphenyl sulphide and diphenyl disulphide, 2,6-bis- 2'-hydroxy-3 -tert.butyl-5 -methylbenzyl 4-methylphenol,
  • polynuclear phenols such as 2-tert.butyl-lhydroxynaphthalene, 4,6-di-tert.butyl-5-hydroxyindane, 5- hydroxyacenaphthene, polyvalent phenols and derivatives thereof: butyl pyrocatechin, octyl gallate, hydroquinone, butylhydroxy anisole, hydroquinone monobenzyl ether.
  • aminohydroxyaryl compounds useful as antioxidant functional fluids according to the invention, those derivatives in which the amino and hydroxyl groups are in pposition to each other are particularly suitable. Examples are: p-hydroxy-diphenylamine, p-hydroxyoctyl aniline, phydroxy-N-y-aminopropyl aniline.
  • Heterocyclic compounds which can be used as antioxidants are exemplified by the following: phenothiazines or iminodibenzyls, e.g. those substituted by higher alkyl; phenosilazines, e.g. 5-ethyll0*,lO-diphenyl-phenosilazine; dihydroquinolines, e.g. 6-methoxyor 6-ethoxyor 6-ethylamino-2,2,4-trimethyl-1,Z-dihydroquinoline, or telomers thereof; or tetrahydroquinolines, e.g. 3-hydroxy-7,8-benzo- 1,2,3,4-tetrahydroquinoline.
  • phenothiazines or iminodibenzyls e.g. those substituted by higher alkyl
  • phenosilazines e.g. 5-ethyll0*,lO-diphenyl-phenosilazine
  • Didodecyl selenide or Topanol CA sold by Imperial Chemical Company a compound of the sterically hindered phenol type, may also be used as antioxidant.
  • additives which improve or modify the properties of lubricant and other functional fluids containing as the essential functional component imides according to the invention can be mixed with the latter.
  • additives are, for instance, antioxidants, high pressure additives, anticorrosives, agents to lower the solidification point and viscosity index improvers and/or thickeners.
  • Suitable high pressure additives in the functional fluids according to the invention are barium or calcium mahogany sulfonates, lower alkyl phosphites, phosphates, sulfurized sperm oil or the like; suitable viscosity index improvers are the polymethacrylate alkyl esters; suitable defoaming agents are, e.g. those based on silicone oil, and suitable anti-corrosives are, e.g. sarcosines and benzotriazoles.
  • compositions of matter which are fluid at room temperature which can be used as functional fluids according to the invention having a thermal stability of at least 360 C. contain at least 25% by weight (calculated on the total weight of the composition) of imides of Formula I and up to 75% by weight of at least one functional fluid based on esters, aromatic ether, silicium compounds, melamines and high boiling mineral oil fractions. The proportions of the mixture in each case depend on the intended purpose.
  • the invention also includes greases consisting of imides as defined and thickeners. Examples of suitable thickeners are metal soaps, montmorillonites, e.g. bentonite, phthalocyanines, violanthrones or graphite.
  • N-ndodecyl-cis-cyclohexane-1,2-dicarboxylic acid imide By distillation under vacuum 699 g. of a product consisting mainly of N-ndodecyl-cis-cyclohexane-1,2-dicarboxylic acid imide are obtained.
  • the technical dodecylamine used contains 99.0% by weight of dodecylamine, 0.3% by weight of decylamine and 0.7% by weight of tetradecylamine. Pure N-n-dodecyl-cis-cyclohexane-1,2-dicarboxylic acid imide boils at 241-242.5/12 torr and the 11 20 is 1.4812.
  • N-n-dodecyl succinimide produced from succinic acid anhydride and technical dodecylamine melts at 54-55 N0.
  • 2.N-n-decyl-cis-cyclohexane 1,2 dicarboxylic acid imide 1290 g. (8.4 mol) of cis-cyclohexane-1,2- dicarboxylic acid anhydride are heated at 120 in a 4.5 litre four-necked flask fitted with two inlet funnels, a
  • thermometer and a combined water separator and reflux condenser 1383 g. (8.8 mol) of technical decylamine (Fettamin 10 D of Farbwerke Hoechst A.G., Frankfurt am Main, Germany) are added dropwise to this mixture within 90 minutes, the temperature of the reaction mixture being kept between 120 and 150. Toluene is added dropwise simultaneously in order to remove the reaction water formed as toluene/water azeotrope from the reaction mixture. The imide formation is complete after 5 hours and the theoretical amount of 151 g. of water is removed. The reaction mixture isdistilled in vacuo. The first fractions, 66 parts, consists mainly of Fettamin D. The main fraction weighs 2460 g.
  • the Fettamin 10 D consists of 1.0% by weight of dodecylamine, 76.4% by weight of n-decylamine, 21.8% by weight of n-octylamine, 0.3% by weight of n-hexylamine and 0.5% by Weight of low boiling impurities.
  • the technical octylamine used for this synthesis boils between 159-179 and consists of 4.5% by weight of n-hexylamine, traces of n-heptylamine, 95.5% by weight of n-octylamine and traces of decylamine.
  • N-n-octyl-ciscyclohexane-1,2-dicarboxylic acid imide boils at 206207/ 11.5 torr; it solidifies below 55 and its refractive index n 20: is 1.4843. In contrast, pure N-n-octyl succinimide melts at 26.527.
  • N0. 4.N-n-hexadecyl-cis-I,2-cycl0hexane-1,2 dicarboxylic acid imide A mixture consisting of g. (0.65 mol) of cis-cyclohexane-1,2-dicarboxylic acid anhydride and 168.5 g. (0.7 mol) of technical n-hexadecylamine, is heated for 3 hours at 165 while removing the reaction water and is then distilled. 238 parts of N-n-hexadexyl-cis-1,Z-cyclohexane-1,2-dicarboxylic acid imide are obtained.
  • the technical hexadecylamine used consists of 84.1% by weight of n-hexadecylamine, traces of n-decylamine, 1.8% by weight of n-dodecylamine, 7.0% by weight of tetradecylamine, 1.1% by weight of pentadecylamine and 6.0% by weight of octadecylamine.
  • N0. 5.N-n--decyl-cis-3,6-end0methylene-cyclohexane- 1,2-dicarb0xylic acid imide A mixture consisting of 328 g. (2 mol) of anhydride of cis-bicyclo[2,2,1]heptene- (2)-5,6-dicarboxylic acid and 333 g. (2.1 mol) of Fettamin 10 D (cf. No. 2) is heated to 150 and the reaction water is continuously removed as azeotrope. Distillation yields 571 g.
  • N-n-dodecyl-cis-3,6-endomethylene-1,2,3,6-tetrahydrophthalic acid imide are obtained, corresponding to 93.0% by weight calculated on the above anhydride.
  • This imide is catalyticaliy hydrogenated with hydrogen in the presence of palladium like No. 5 and then fractionated whereupon a mixture consisting mainly of N-n-dodecylcis-3,6-endomethylene cyclohexane-1,2-dicarboxylic acid imide is obtained.
  • Example 1 Imide No. l is suitable for lubricating metal surfaces. To attain a quantitative comparison of its lubricant action with five usual commercial lubricants, the scar diameter was measured in a 4-ball wear machine. These measurements were obtained according to US. Federal Specifications Lubricants and related Products VV-L 791e. Method 6503: Load Carrying Capacity (means Hertz Load). This apparatus ran for 30 minutes at a speed of 1480 revs. per minute with a load of 40 kg.
  • cinimide can only be heated to at most 380.
  • the useful liquid range of imide No. 1 is also extended by at least 60 compared with the corresponding succinimide.
  • Example 3 S diameter m To test the stability necessary for the lubricant powers substanfie used: (average of 3 measumments) of the imides according to the invention under oxidative n 1 0545 conditions, 25 ml. of the substance were exposed at a f' Sebacate 0-817 constant temperature to a stream of air of 2 litres per Dl'z'ethylhexyl SePacate 0-850 hour for 6 hours and the aldehydes formed by reaction Y Y adlpate 0-915 with hydroxylamine hydrochloride were acidimetrically Mineral oil (viscosity at 100 F.: 65.7 cst.) 0.898 Pentaphenyl ether (voscosity at 100 F.: 369
  • Example 2 The imides Nos. 1-6 are also suitable at very high temperatures as lubricants and heat-transferring agents.
  • the imides were tested as follows as to the thermal stability necessary for such uses:
  • This table also shows other physical data of the compounds from which the suitablility of these stable, difficultly volatile imides as functional fluids and/or lubricants can be seen.
  • Column II shows the viscosity measured at 100 F. (37.8 C.) and at 210 F. (98.8 C.) in centistokes
  • column III gives the so-called A.S.T.M. slope determined with the aid of the A.S.T.M. Standard Viscosity-Temperature Chart for Liquid Petroleum Products (Method D 341) at 100 F. and 210 F.
  • a value of over 1.0 means that the fluid is only very slightly suitable.
  • A.S.T.M. is an abbreviation for American Society for Testing Materials, 1961 Race St., Philadelphia, Pa., U.S.A.
  • imide No. 1 can stand heating up to 400 whereas the analogous dodecyl sucdetermined. This showed that imide No. 3 at a test temperature of 260 was more slowly oxidised than the corresponding succinimide at a test temperature of 226. This means that imides according to the invention can be used under oxidative conditions at at least 34 higher temperatures than the corresponding succinimide.
  • Example 4 A decisive property of a lubricant is that the system operated therewith can be advantageously sealed.
  • a strip of Viton A rubber which is suitable as gasket material (Viton A is a synthetic special rubber consisting of vinylidene fluoride-hexafiuoropropene mixed polymer made by Du Pont Co., Wilmington, Del, U.S.A.), the dimensions of which strip were 25.4 x 25.4 x 1.6 mm., was heated for 150 hours at 110 in imide No. 1. The increase in volume of the strip was +10.83%. The hardness was changed by 7.6 degrees.
  • a similar Viton A rubber strip was tested analogously in imide No. 2. In this case the increase in volume was +285 6% and hardness was altered by 13.8 degrees.
  • the imides Nos. 3-6 had a similar effect on Viton A rubber.
  • the imides Nos. 1-6 produced swell values with commercial silicon rubber similar to those produced with Viton A rubber. This also shows that the above imides do not unduly alter the nature of the tested sealing materials.
  • Example 5 In order to adapt the properties of lubricants and heat-transferring fluids to the desired use, it is important that they can be mixed with other base stocks. To test the behaviour of the imides according to the invention in this respect, tests were made as to their miscibility at 25 With various usual commercial lubricants and heattransferring agents. The mixtures produced were observed for 20 consecutive days at 0 and their viscosity was measured at the beginning and the end of this observation time. The viscosity in centistokes of the pure lubricant-s as well as of mixtures thereof was determined at F. (37.8 C.) and 210 F. (98.8 C.) and is given in column V of Table 3. Column VI shows the A.S.T.M. slope.
  • Both at 0 and at 25 imide No. 2 can also be mixed Example 7 in any proportion with a bis-(phenoxyphenyl)-ether, (e.g. 99 of imide Na 2 and 1 of iminodibenzyl are DOW ET'378 3 Dow chemllgal 11, g g stirred together until the latter has completely dissolved.
  • i i exyl S1 mate me y Compared with the pure imide, the mixture obtained has phenyl s1l1con 011 (cg. s1l1con DC 550 Fluid of Dow S O f Mu improved stability to oxidatlon. Corn1ng Co., Midland, Mich. U.S.A.
  • the mass obtained is heated for 2 hours at 150 99 8 f N 2 d 0 2 f b I and after cooling is again Worked with a spatula.
  • the 2 1 9 g fi are product so formed is a soft grease which can be Well i h ollnpar 2 pure P e mlxmre Worked up. It was found to have the following greasing i as 658 corroslve ac Damon M y on Copper properties and its alloys.
  • adel-phia, Pa., U.S.A. as visocsity improver, are homo- 1 l geneously mixed by stirring. This mixture has :a lower solidification point than the pure imide No. 1.
  • a method of lubricating hydraulically operating parts of a mechanical system in frictional engagement with each other comprising inserting between said parts so engaged a film of an imide of the formula CH CO Carma I N-R OH wherein R and R" each represent hydrogen and taken together, they represent a lower alkylene group of from 1 to 2 carbon atoms, and
  • R represents an alkyl group of from 6 to 18 carbon atoms in a straight chain
  • a functional fluid consisting essentially of a major amount of an imide of the formula CH C O wherein R' and R" each represent hydrogen and taken together, they represent a lower alkylene group of from 1 to 2 carbon atoms, and
  • R represents an alkyl group of from 6 to 18 carbon atoms in a straight chain
  • the balance consisting of a minor amount of at least one adjuvant selected from the group consisting of an antioxidant compatible with and stabilizing said imide, an anticorrosive agent capable of protecting metal surface in contact with said imide against corrosion by the latter, an anti-foaming agent compatible with said imide, and a polymethacrylate viscosity index improver.
  • an adjuvant selected from the group consisting of an antioxidant compatible with and stabilizing said imide, an anticorrosive agent capable of protecting metal surface in contact with said imide against corrosion by the latter, an anti-foaming agent compatible with said imide, and a polymethacrylate viscosity index improver.
  • a grease consisting essentially of a major amount of an imide of the formula wherein R and R" each represent hydrogen and taken together, they represent a lower alkylene group of from 1 to 2 carbon atoms, and
  • R represents an alkyl group of from 6 to 18 carbon atoms in a straight chain
  • the balance consisting of a minor amount of at least one adjuvant selected from the group consisting of an antioxidant compatible with and stabilizing said imide, an anticorrosive agent capable of protecting metal surface in contrast with said imide against corrosion by the latter, an anti-foaming agent compatible with said imide,
  • a composition consisting of at least 25% and up to by weight of a lubricant imide of the formula orn R o I om n" wherein R and R" each represent hydrogen and taken together, they represent a lower alkylene group of from 1 to 2 carbon atoms, and
  • R represents an alkyl group of from 6 to 18 carbon atoms in a straight chain
  • a functional fluid as defined in claim 2 wherein the imide in N-n-decyl-cyclohexane 1,2 dicarboxylic acid imide is N-n-decyl-cyclohexane 1,2 dicarboxylic acid imide.
  • a functional fluid as defined in claim 2 wherein the imide is N-n-dodecyl-cyclohexane-1,2-dicarboxylic acid imide.
  • a functional fluid as defined in claim 2 wherein the imide is N-n-octyl cyclohexane 1,2 dicarboxylic acid imide.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
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US454678A 1964-05-12 1965-05-10 Cyclohexane-dicarboxylic imide type functional fluids Expired - Lifetime US3317427A (en)

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CH614364A CH445698A (de) 1964-05-12 1964-05-12 Verwendung von flüssigen Imiden als technisches Öl

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3078228A (en) * 1959-11-06 1963-02-19 Houghton & Co E F Imide compounds and lubricants containing the same
US3151079A (en) * 1961-09-05 1964-09-29 Dow Chemical Co Polyphenyl ether stabilizers
US3208939A (en) * 1963-12-12 1965-09-28 Universal Oil Prod Co Stabilization of organic substances

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3078228A (en) * 1959-11-06 1963-02-19 Houghton & Co E F Imide compounds and lubricants containing the same
US3151079A (en) * 1961-09-05 1964-09-29 Dow Chemical Co Polyphenyl ether stabilizers
US3208939A (en) * 1963-12-12 1965-09-28 Universal Oil Prod Co Stabilization of organic substances

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DE1276853B (de) 1968-09-05

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