AU2012261221A1

AU2012261221A1 - High temperature oil

Info

Publication number: AU2012261221A1
Application number: AU2012261221A
Authority: AU
Inventors: Karl Egersdorfer; Thomas Kilthau; Martin Schmidt-Amelunxen
Original assignee: Klueber Lubrication Muenchen SE and Co KG
Current assignee: Klueber Lubrication Muenchen GmbH and Co KG
Priority date: 2011-05-26
Filing date: 2012-05-22
Publication date: 2013-12-12
Anticipated expiration: 2032-05-22
Also published as: DE102011102540B4; MY164068A; US20140200169A1; AU2012261221B2; ES2601401T3; CN103764808A; BR112013030286B1; LT2714872T; PL2714872T3; KR20140009499A; JP2014515412A; HUE029149T2; EP2714872A1; EA026445B1; BR112013030286A2; EA201301331A1; JP5752321B2; WO2012159738A1; CL2013003397A1; SI2714872T1

Abstract

The invention relates to novel high temperature oils based on aromatic esters, such as trimellitic acid esters, pryomellitic acid esters, trimesic acid esters or a mixture thereof or derivatives of phloroglucinol and a fully hydrated or a hydrated polyisobutylene or a mixture thereof.

Description

WO 2012/159738 PCT/EP2012/002172 High temperature oil Description 5 The invention relates to novel high-temperature oils based on aromatic esters such as trimellitic esters, pyromellitic esters, trimesic esters or a mixture, or derivatives of phloroglucinol such as phloroglucinol trioctanoate, phloroglucinol tridecanoate and 10 phloroglucinol tridodecanoate thereof, and a fully hydrogenated or a hydrogenated polyisobutylene or a mixture thereof. High-temperature oils which are used in the field of 15 industrial chain lubrication, for example in conveying systems, painting lines, the textile industry, the insulating materials industry, the glass industry, etc., and belt lubrication in continuous wood pressing plants, typically consist of a three-component system. 20 This three-component system generally consists of an aromatic ester, a synthetic hydrocarbon and a polymer based on polyisobutylene. The synthetic hydrocarbon is used as a solubilizer. Also added to this lubricant 25 system are commercial additives. However, a disadvantage of these systems is that the use of the synthetic hydrocarbon limits the working temperature of the oil, since it vaporizes very rapidly at temperatures > 200 0 C. 30 A three-component system is described, for example, in EP 1 154 011 Bl. Here, a lubricant oil composition comprising an aromatic ester compound and, as a further base oil, an a-olefin oligomer, and also a 35 polyisobutene, is provided. As already stated above, the loss of performance for a WO 2012/159738 PCT/EP2012/002172 -2 three-component lubricant composition is high as a result of the vaporization of the solubilizer. The vaporization results in formation of a deposit or a residue formed from the remaining constituents of the 5 lubricant on the application surface or the application area, as a result of which full lubrication can no longer be ensured. This deposit then has to be dissolved again. In general, operation has to be stopped and the residue has to be removed. There is 10 thus a need for a high-temperature oil in which the vaporization of individual constituents of the oil is greatly reduced and hence the lubricity is not lost at constantly high temperature over a long period. 15 Such a high-temperature oil is especially required for chain and belt lubrication of wood presses, as present, for example, in Contipressen TM continuous presses for the production of laminate floors. 20 It was an object of the present invention to provide a high-temperature oil with which good lubricity is achieved at constantly high temperature over a long period and which can be provided in different viscosities according to the application. 25 This object is surprisingly achieved by the provision of a high-temperature oil which consists, as a two component system 30 an aromatic ester of the general formula (I) ~ ( COQRI)n where R1 is a linear or branched alkyl group having 6 35 to 16 carbon atoms and n is 3 or 4, WO 2012/159738 PCT/EP2012/002172 -3 or a compound of the general formula (II) 0 R 5 where R is a linear or branched alkyl group having a chain length of 8 to 16 carbon atoms and n is equal to 3, and a hydrogenated polyisobutylene, a fully hydrogenated 10 polyisobutylene or a mixture of a fully hydrogenated and a hydrogenated polyisobutylene. Preferably, a fully hydrogenated polyisobutylene is included. In general, the high-temperature oil comprises 40 to 15 91.9% by weight of the aromatic ester of the general formula (I) or of the compound of the general formula (II) and 50 to 5% by weight of the hydrogenated, fully hydrogenated polyisobutylene or of a mixture of hydrogenated and fully hydrogenated polyisobutylene. 20 In addition, the high-temperature oil may comprise 0.1 to 6% by weight, especially 2 to 5% by weight, of an antioxidant. 25 The high-temperature oil may also comprise 0 to 4% by weight, especially 0.3 to 3.5% by weight, of an antiwar agent, 0.1 to 1.0% by weight of an anticorrosive, and 0 to 2% by weight, especially 0.1 to 1.5% by weight, of an ionic liquid. 30 The ester compound of formula (I) present in the high temperature oil is preferably selected from the group consisting of esters of trimellitic acid, pyromellitic WO 2012/159738 PCT/EP2012/002172 -4 acid, trimesic acid or mixtures thereof. The compound of the general formula (II) is a derivative of phloroglucinol (benzene-1,3,5-triol), preferably phloroglucinol trioctanoate, phloroglucinol 5 tridecanoate and phloroglucinol tridodecanoate. The antioxidant present in the high-temperature oil, which may contain sulfur and/or nitrogen and/or phosphorus in the molecule, is selected from the group 10 consisting of aromatic aminic antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldi phenylamine, sterically hindered phenols such as butylhydroxytoluene (BHT), phenolic antioxidants having thioether groups, zinc dialkyldithiophosphates or 15 molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, and phosphites. The antiwear agent present in the high-temperature oil is selected from the group consisting of antiwear 20 additives based on diphenyl cresyl phosphate, amine neutralized phosphates, alkylated and nonalkylated triaryl phosphates, alkylated and nonalkylated triaryl thiophosphates, zinc dialkyldithiophosphates or molybdenum dialkyldithiophosphates or tungsten 25 dialkyldithiophosphates, carbamates, thiocarbamates, zinc dithiocarbamates or molybdenum dithiocarbamates or tungsten dithiocarbamates, dimercaptothiadiazole, calcium sulfonates and benzotriazole derivatives. 30 The anticorrosive present in the high-temperature oil is selected from the group consisting of additives based on "overbased" calcium sulfonates having a TBN of 100 to 300 mg KOH/g, amine-neutralized phosphates, alkylated calcium naphthalenesulfonates, oxazoline 35 derivatives, imidazole derivatives, succinic monoesters, N-alkylated benzotriazoles.

WO 2012/159738 PCT/EP2012/002172 -5 The ionic liquid (IL) used in the high-temperature oil comprises what are called salt melts which, by definition, are liquid at temperatures below 100 0 C. Many ionic liquids are also liquid at room temperature 5 or at lower temperatures. Suitable cations for ionic liquids have been found to be a quaternary ammonium cation, a phosphonium cation, an imidazolium cation, a pyridinium cation, a pyrazolium cation, an oxazolium cation, a pyrrolidinium cation, a guanidinium cation, a 10 morpholinium cation or a triazolium cation, which may be combined with an anion selected from the group consisting of [PF 6 ], [BF 4 ] , [CF3CO 2 ] , [CF3SO3], [ (CF3SO 2 ) 2N] , [ (R 4 S0 2 ) (R 5 S0 2 )N]-, [ (CF 3

SO

2 ) (CF3COO) N],

[R

4 -SO3], [R 4 -0-SO3] , [R 4 -COO] , ClE, Br, [NO 3 ], 15 [N(CN) 2 ] , [HSO 4 ] , or [R 4

R

5 P0 4 , and the R 4 and R 5 radicals are each independently selected from hydrogen; linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups having 1 to 20 carbon atoms; heteroaryl groups, heteroaryl-Ci-C 6 -alkyl groups having 20 3 to 8 carbon atoms in the heteroaryl radical and at least one heteroatom from N, 0 and S which may be substituted by at least one group selected from Ci-C 6 alkyl groups and/or halogen atoms; aryl groups, aryl Ci-C 6 -alkyl groups having 5 to 12 carbon atoms in the 25 aryl radical, which may be substituted by at least one Ci-C 6 -alkyl group, partly and fully fluorinated alkyl radicals. However, further combinations are also possible. Anions of [PF( 6 -x)R 7 x], [R 7 -SO3 type are also known. R 7 here represents partly or fully fluorinated 30 radicals such as pentafluoroethyl or perfluorobutyl. The following anion type is likewise quite thermally stable: (FSO 2

)

2 N-. In order to display positive action in oils, the ionic 35 liquids should firstly show solubility in the oils, although complete miscibility is not absolutely necessary. The ionic liquids should be thermally stable WO 2012/159738 PCT/EP2012/002172 -6 and not promote corrosion, for example by forming reaction products which are noncorrosive or corrosive only in a very delayed manner in the presence of water. 5 Particularly advantageous ionic liquids have been found to be those such as tetraalkylammonium bis(trifluoromethylsulfonyl)imides and tetraalkyl phosphonium bis(trifluoromethylsulfonyl)imides, for example trihexyl(tetradecyl)phosphonium bis(trifluoro 10 methylsulfonyl)imide (HPDimide) and methyltri octylammonium bis (trifluoromethylsulfonyl) imide (Moimide). Ionic liquids which have likewise been found to be particularly advantageous are those such as tetraalkylammonium tris (perfluoroethyl) trifluoro 15 phosphate and tetraalkylphosphonium tris(perfluoro ethyl)trifluorophosphate, for example tetrabutyl phosphonium tris(perfluoroethyl)trifluorophosphate (BuPPFET), trihexyl(tetradecyl) tris(perfluoroethyl) trifluorophosphate (HDPPFET). It has likewise been 20 found that pyrrolidinium tris(perfluoroethyl)trifluoro phosphates are particularly advantageous. Also particularly advantageous are tetraalkylammonium perfluorobutanesulfonates and tetraalkylphosphonium perfluorobutanesulfonates such as trihexyl(tetradecyl) 25 phosphonium perfluorobutanesulfonate (HDPnonaflate). It is also possible to use any desired mixtures of the ionic liquids. 30 The inventive two-component system has a much higher performance in terms of thermal stability and residue formation or residue characteristics. The enormous rise in thermal stability is manifested particularly in a distinct increase in lubrication characteristics. The 35 relubrication intervals were extended and an energy saving of up to a 30% power saving was achieved.

WO 2012/159738 PCT/EP2012/002172 -7 As already mentioned, the formation of residues is distinctly reduced. As a result, the formation of cracking residues is also reduced and the residues formed can be very easily dissolved with fresh oil. 5 The appended figures show the advantages of the inventive high-temperature oil based on two components. Figure 1 shows the friction values as a function of 10 temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic 15 viscosity at 40 0 C of about 260 mm 2 /sec; figure 2 shows the vaporization losses for an inventive high-temperature oil based on two components from example 1 compared with a 20 known oil based on three components from comparative example 1 at a kinematic base oil viscosity at 40 0 C of about 260 mm 2 /sec; figure 3 shows the increase in the apparent dynamic 25 viscosity of an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic base oil viscosity at 40 0 C of 30 about 260 mm 2 /sec; figure 4 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two 35 components from example 2 compared with a known oil based on three components from comparative example 2; WO 2012/159738 PCT/EP2012/002172 -8 figure 5 shows the vaporization losses for an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from 5 comparative example 2 at a kinematic base oil viscosity at 40 0 C of about 100 mm 2 /sec; figure 6 shows the increase in the apparent viscosity of an inventive high-temperature oil based 10 on two components from example 2 compared with a known oil based on three components from comparative example 2 at a kinematic base oil viscosity at 40 0 C of about 100 mm 2 /sec; 15 figure 7 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 3 compared with a 20 known oil based on three components from comparative example 3; figure 8 shows the vaporization losses for an inventive high-temperature oil based on two 25 components from example 3 compared with a known oil based on three components from comparative example 3 at a kinematic base oil viscosity at 40 0 C of about 680 mm 2 /sec; 30 figure 9 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3 at a 35 kinematic base oil viscosity at 40 0 C of about 680 mm 2 /sec; figure 10 shows the vaporization losses for an WO 2012/159738 PCT/EP2012/002172 -9 inventive high-temperature oil based on two components with an ionic liquid from example 4 compared with comparative example 4, which corresponds to example 1 at a kinematic base 5 oil viscosity of about 260 mm 2 /sec; figure 11 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components with an ionic 10 liquid from example 4 compared with comparative example 4, which corresponds to example 1 at a kinematic base oil viscosity of about 260 mm 2 /sec; 15 figure 12 shows the experimental setup for the high performance chain test bed. The invention is now illustrated in detail by the examples which follow. 20 Example 1 Production of an inventive two-component high temperature oil 25 Composition of the high-temperature oil: 63.4% by weight of aromatic trimellitic ester 30.0% by weight of fully hydrogenated polyisobutylene 3.5% by weight of antiwear agent 3.0% by weight of antioxidant 30 0.1% by weight of anticorrosive As the aromatic ester, trimellitic ester is initially charged in a stirred tank. At 100 0 C, the polyisobutylene is added while stirring. Subsequently, 35 the mixture is stirred for one 1 hour in order to obtain a homogeneous mixture. The antiwear agent and the antioxidant are added to the tank at 60 0 C while WO 2012/159738 PCT/EP2012/002172 - 10 stirring. After about 1 hour, the finished oil can be dispensed into the containers provided. Comparative example 1 5 Production of a known three-component high-temperature oil Composition of the high-temperature oil: 47.4% by weight of aromatic trimellitic ester 10 16.0% by weight of polyisobutylene 30.0% by weight of synthetic hydrocarbon 3.5% by weight of antiwear agent 3.0% by weight of antioxidant 0.1% by weight of anticorrosive 15 As the aromatic ester, trimellitic ester is initially charged in a stirred tank together with the poly-a olefin as the synthetic hydrocarbon. At 100 0 C, the polyisobutylene is added while stirring. Subsequently, 20 the mixture is stirred for 1 hour in order to obtain a homogeneous mixture. The antiwear agent and the antioxidant are added to the tank at 60 0 C while stirring. After about 1 hour, the finished oil can be dispensed into the containers provided. 25 The advantages of the inventive high-temperature oil are shown hereinafter. The base data for the oil according to example 1 and 30 comparative example 1 are shown in table 1.

WO 2012/159738 PCT/EP2012/002172 - 11 Table 1 Example 1 Comparative example 1 Appearance clear clear Kinematic viscosity 271 mm 2 /sec 275 mm 2 /sec 40 0 C Kinematic viscosity 24 mm 2 /sec 25 mm 2 /sec 1000C Flashpoint > 250 0 C > 250 0 C Pour point -30 0 C -30 0 C 1.1. Thermal stability studies 5 Studies were conducted with regard to vaporization and viscosity under thermal stress on a starting weight of 5 g in an aluminum pan at 230 0 C. For this purpose, the oils according to example 1 and comparative example 1 10 were compared with one another.

WO 2012/159738 PCT/EP2012/002172 - 12 Table 2 Example 1 Comparative example 1 Vaporization loss 16% 30% after 24 h/230 0 C Vaporization loss 25% 49% after 48 h/230 0 C Vaporization loss 35% 62% after 72 h/230 0 C Increase in 970 mPas 1300 mPas apparent dynamic viscosity after 24 h/230 0 C Increase in 1400 mPas 4400 mPas apparent dynamic viscosity after 48 h/230 0 C Increase in 3200 mPas 41 000 mPas apparent dynamic viscosity after 72 h/230 0 C The above results show that the use of fully 5 hydrogenated polyisobutylene in a two-component high temperature oil can distinctly reduce the rise in viscosity and in the vaporization loss compared to the known three-component oil. These results are also shown in the form of graphs in figures 2 and 3. 10 1.2. Comparison of the friction values The oils produced in example 1 and comparative example 1 were used for determination of the friction values. 15 For this purpose, an oscillating frictional wear test (SRV) was conducted based on DIN 51834, ball/disk test condition, load 250 N, 50 0 C to 250 0 C, stroke 1 mm, WO 2012/159738 PCT/EP2012/002172 - 13 50 Hz, 165 min. The results are shown in table 3. Table 3 SRV TST 250 N point Example 1 Comparative Friction number example 1 Friction number 50 to 120 0 C 0.104 0.109 to 140 0 C 0.105 0.109 to 160 0 C 0.102 0.118 to 180 0 C 0.096 0.128 to 200 0 C 0.090 0.138 to 210 0 C 0.087 0.145 to 220 0 C 0.087 0.151 to 230 0 C 0.091 0.159 to 240 0 C 0.102 0.166 to 250 0 C 0.110 0.169 5 These results, which are also shown in figure 1, show the positive effect of the high-temperature oil based on two components on the friction number compared to the three-component system. 10 1.3. Residue characteristics after complete vaporization of the oil at 250 0 C The formation of residues and the behavior of the 15 residues with regard to solubility were studied. The oil to be tested is weighed to 5 g onto a steel sheet which has been bent to size and cleaned with solvent beforehand, and then vaporized off at 250 0 C in 20 an air circulation drying cabinet for min. 72 h. The square sheet is bent manually on all four sides, so as to give a dish shape. After cooling, the results of the re-weighing are documented.

WO 2012/159738 PCT/EP2012/002172 - 14 Important features for this test are the determination of the dissolvability of the residue surface with fresh oil and the amount of residue formed. For this purpose, a drop of the fresh oil is applied to 5 the residue and rubbed in gently by means of a rounded glass rod with circular movements. The results show that the inventive high-temperature oil forms a lower level of residue at 4.8% than the 10 known oil, which has a residue of 6.0%. The residue formed from the inventive high-temperature oil has very good surface dissolvability, which means that these residues are easy to dissolve with fresh oil. In contrast, the residue of the known oil has much poorer 15 surface redissolvability with fresh oil. 1.4. High-performance chain test bed Figure 12 shows the high-performance chain test bed, 20 which works under the following test conditions: Temperature: 220 0 C Speed: 2 m/sec Load: 2600 N 25 Run time after 0.1% chain lengthening 22 hours for example 1, and 17 hours for comparative example 1. Before the test, the chain is immersed into the lubricant oil to be tested. After the immersion, the 30 chain is suspended, such that the excess lubricant can drip off. Subsequently, the chain is installed into the chain test bed (see figure 10) and the test is started under the conditions defined. It is possible to vary the temperature, the speed and the load. 35 The run time is fixed at a chain lengthening of 0.1%. The lengthening of the chain arises through wear at the chain members during the test run.

WO 2012/159738 PCT/EP2012/002172 - 15 Example 2 Composition of the inventive high-temperature oil: 82% by weight of aromatic trimellitic ester 5 12.7% by weight of fully hydrogenated polyisobutylene 0.3% by weight of antiwear agent 4.5% by weight of antioxidant 0.5% by weight of anticorrosive 10 The production is effected as described in example 1. Comparative example 2 Composition of the three-component high-temperature oil: 15 55.7% by weight of aromatic trimellitic ester 7% by weight of polyisobutylene 33.20% by weight of synthetic hydrocarbon 0.30% by weight of antiwear agent 20 3.7% by weight of antioxidant 0.10% by weight of anticorrosive The production is effected as described in comparative example 1. 25 The advantages of the inventive high-temperature oil are shown hereinafter. The base data for the oil according to example 2 and 30 comparative example 2 are shown in table 4.

WO 2012/159738 PCT/EP2012/002172 - 16 Table 4 Viscosity at 40 0 C, Example 2 Comparative 100 mm 2 /sec example 2 Appearance clear clear Kinematic viscosity 120.0 mm 2 /sec 107.0 mm 2 /sec 40 0 C Kinematic viscosity 14 mm 2 /sec 13.5 mm 2 /sec 1000C Flashpoint > 250 0 C > 250 0 C Pour point -20 0 C -30 0 C 2.1. Thermal stability studies 5 Studies were conducted with regard to the vaporization and viscosity under thermal stress on a starting weight of 5 g in an aluminum pan at 230 0 C. For this purpose, the oils according to example 2 and comparative example 10 2 were compared with one another.

WO 2012/159738 PCT/EP2012/002172 - 17 Table 5 Example 2 Comparative example 2 Vaporization loss 18% 36% after 24 h/230 0 C Vaporization loss 37% 57% after 48 h/230 0 C Vaporization loss 52% 71% after 72 h/230 0 C Increase in 340 mPas 430 mPas apparent dynamic viscosity after 24 h/230 0 C Increase in 1250 mPas 200 mPas apparent dynamic viscosity after 48 h/230 0 C Increase in 4700 mPas 23 000 mPas apparent dynamic viscosity after 72 h/230 0 C The above results show that the use of fully 5 hydrogenated polyisobutylene in a two-component high temperature oil can distinctly reduce the rise in viscosity and in the vaporization loss compared to the known three-component oil. These results are also shown as graphs in figures 5 and 6. 10 2.2. Comparison of the friction values The oils produced in example 2 and comparative example 2 were used to determine the friction values. For this 15 purpose, an oscillating frictional wear test (SRV) was conducted based on DIN 51834, ball/disk test condition, load 250 N, 50 0 C to 250 0 C, stroke 1 mm, 50 Hz, 165 min.

WO 2012/159738 PCT/EP2012/002172 - 18 The results are shown in table 6. Table 6 SRV TST 250 N point Example 2 Comparative Friction number example 2 Friction number 50 to 120 0 C 0.097 0.105 to 140 0 C 0.093 0.112 to 160 0 C 0.122 0.129 to 180 0 C 0.133 0.136 to 200 0 C 0.138 0.143 to 210 0 C 0.139 0.157 to 220 0 C 0.136 0.175 to 230 0 C 0.138 0.186 to 240 0 C 0.136 0.196 to 250 0 C 0.136 0.205 5 These results, which are also shown in figure 4, show the positive effect of the high-temperature oil based on two components on the friction number compared to the three-component system. 10 2.3. Residue characteristics after complete vaporization of the oil at 250 0 C The formation of residues and the behavior of the 15 residues in terms of solubility were studied. The method is described in example 1. Both the inventive high-temperature oil and the known oil had a residue of 3.0%; the residue formed from the 20 inventive high-temperature oil had very good surface dissolvability, which means that these residues can be dissolved easily with fresh oil. In contrast, the residue of the known oil has much poorer surface redissolvability with fresh oil.

WO 2012/159738 PCT/EP2012/002172 - 19 2.4. High-performance chain test bed The test on the high-performance chain test bed was conducted at 220 0 C, a speed of 2.0 m/sec and a load of 5 2600 N. The run time after chain lengthening 0.1% is 19 h for example 2, and that for comparative example 2 is 17 h. The test was conducted as described in example 1. 10 Example 3 Composition of the inventive high-temperature oil: 45.4% by weight of aromatic trimellitic ester 48.00% by weight of fully hydrogenated polyisobutylene 15 2.5% by weight of antiwear agent 3.0% by weight of antioxidant 0.1% by weight of anticorrosive The production was effected as described in example 1. 20 Comparative example 3 Composition of the three-component high-temperature oil: 25 47.0% by weight of aromatic trimellitic ester 17.4% by weight of polyisobutylene 29.0% by weight of synthetic hydrocarbon 3.5% by weight of antiwear agent 3.0% by weight of antioxidant 30 0.10% by weight of anticorrosive The production was effected as described in comparative example 1. 35 The advantages of the inventive high-temperature oil are shown hereinafter.

WO 2012/159738 PCT/EP2012/002172 - 20 The base data for the oil according to example 3 and comparative example 3 are shown in table 7. Table 7 5 Viscosity at 40 0 C, Example 3 Comparative 680 mm 2 /sec example 3 Appearance clear clear Kinematic viscosity 690 mm 2 /sec 690 mm 2 /sec 40 0 C Kinematic viscosity 24 mm 2 /sec 47 mm 2 /sec 1000C Flashpoint > 250 0 C > 250 0 C Pour point -30 0 C -30 0 C 3.1. Thermal stability studies Studies were conducted with regard to vaporization and 10 viscosity under thermal stress on a starting weight of 5 g in an aluminum pan at 230 0 C. For this purpose, the oils according to example 3 and comparative example 3 were compared with one another. 15 WO 2012/159738 PCT/EP2012/002172 - 21 Table 8 Example 3 Comparative example 3 Vaporization loss 18% 20% after 24 h/230 0 C Vaporization loss 28% 38% after 48 h/230 0 C Vaporization loss 37% 53% after 72 h/230 0 C Increase in 3400 mPas 2800 mPas apparent dynamic viscosity after 24 h/230 0 C Increase in 6000 mPas 13 250 mPas apparent dynamic viscosity after 48 h/230 0 C Increase in 12 700 mPas 47 000 mPas apparent dynamic viscosity after 72 h/230 0 C The above results show that the use of fully 5 hydrogenated polyisobutylene in a two-component high temperature oil can reduce the rise in viscosity and in the vaporization loss compared to the known three component oil. These results are also shown as graphs in figures 8 and 9. 10 3.2. Comparison of the friction values The oils produced in example 3 and comparative example 3 were used to determine the friction values. For this 15 purpose, an oscillating frictional wear test (SRV) was conducted based on DIN 51834, ball/disk test condition, load 250 N, 50 0 C to 250 0 C, stroke 1 mm, 50 Hz, 165 min.

WO 2012/159738 PCT/EP2012/002172 - 22 The results are shown in table 9. Table 9 SRV TST 250 N point Example 3 Comparative Friction number example 3 Friction number 50 to 120 0 C 0.119 0.118 to 140 0 C 0.116 0.115 to 160 0 C 0.119 0.114 to 180 0 C 0.115 0.110 to 200 0 C 0.105 0.108 to 210 0 C 0.098 0.105 to 220 0 C 0.096 0.102 to 230 0 C 0.099 0.102 to 240 0 C 0.112 0.089 to 250 0 C 0.126 0.086 5 These results, which are also shown in figure 7, show the positive effect of the high-temperature oil based on two components on the friction number compared to the three-component system. 10 3.3. Residue characteristics after complete vaporization of the oil at 250 0 C The formation of residues and the behavior of the 15 residues in terms of solubility were studied. The test was conducted as described in example 1. The results show that the inventive high-temperature oil forms a lower level of residues at 4.8% than the 20 known oil, which has a residue of 11.8%. The residue formed from the inventive high-temperature oil has very good surface dissolvability, which means that these residues can be dissolved easily with fresh oil. In contrast, the residue of the known oil has much poorer WO 2012/159738 PCT/EP2012/002172 - 23 surface redissolvability with fresh oil. 3.4. High-performance chain test bed 5 The test on the high-performance chain test bed was conducted at 220 0 C, a speed of 2.0 m/sec and a load of 2600 N. The run time after chain lengthening 0.1% was 17 h for example 3 and 15 h for comparative example 3. The test was conducted as described in example 1. 10 Example 4 Composition of the inventive high-temperature oil: 62.90% by weight of aromatic trimellitic ester 15 30.00% by weight of fully hydrogenated polyisobutylene 3.5% by weight of antiwear agent 3.0% by weight of antioxidant 0.1% by weight of anticorrosive 0.50% by weight of ionic liquid 20 The production was effected as described in example 1. The ionic liquid used was HDP imide trihexyl(tetradey-phosphonium bis(trifluoromethyl sulfonyl)imide). 25 Comparative example 4 (corresponds to example 1) Composition of the inventive high-temperature oil: 30 63.40% by weight of aromatic trimellitic ester 30.00% by weight of fully hydrogenated polyisobutylene 3.5% by weight of antiwear agent 3.0% by weight of antioxidant 0.1% by weight of anticorrosive 35 The production was effected as described in example 1.

WO 2012/159738 PCT/EP2012/002172 - 24 The base data for the oil according to example 4 and comparative example 4 are shown in table 10. Table 10 5 Viscosity at 40 0 C, Example 4 Comparative 200 mm 2 /sec example 4 (corresponds to ex. 1) Appearance clear clear Kinematic viscosity 270.0 mm 2 /sec 271.0 mm 2 /sec 40 0 C Kinematic viscosity 24 mm 2 /sec 25 mm 2 /sec 1000C Flashpoint > 250 0 C > 250 0 C Pour point -30 0 C -30 0 C 4.1. Thermal stability studies Studies were conducted with regard to the vaporization 10 and viscosity under thermal stress on a starting weight of 5 g in a closed aluminum pan at 250 0 C. The vaporization loss after 72 h/250 0 C was 19%. The increase in apparent dynamic viscosity in mPas after 72 h/250 0 C was 2300 mPas. 15 WO 2012/159738 PCT/EP2012/002172 - 25 Table 11 Example 4 Comparative example 4 Corresponds to example 1 Vaporization loss 19% 46% after 72 h/250 0 C Increase in 2300 mPas 27 000 mPas apparent dynamic viscosity after 72 h/250 0 C The above results show that the use of HDP imide can 5 once again significantly improve the thermal stability of a two-component system. These results are also shown as graphs in figures 10 and 11. Example 5 10 Composition of the inventive high-temperature oil: 63.5% phloroglucinol tridecanoate 30.0% fully hydrogenated polyisobutylene 3.5% antiwear agent 15 3.0% antioxidant 0.1% by weight of anticorrosive The production was effected as described in example 1. 20 It was also possible to obtain the results described in detail above with the high-temperature oil based on a derivative of phloroglucinol. The above experimental results show that the inventive 25 high-temperature oil in all studies conducted gave much better values than in the case of the known high temperature oils.

WO 2012/159738 PCT/EP2012/002172 - 26 In summary, it can be stated that the inventive two component system has much higher performance with regard to thermal stability and residue formation or residue characteristics. The enormous rise in thermal 5 stability is manifested particularly in a distinct rise in lubrication characteristics. The relubrication intervals were extended and an energy saving of up to a 30% power saving was achieved.

Claims

1. A high-temperature oil for lubrication of chains, chain rollers and belts of continuous presses, 5 comprising 40 to 91.9% by weight of an aromatic ester of the general formula (I) CQQRI)n where R1 is a linear or branched alkyl group 10 having 6 to 16 carbon atoms and n is an integer of 3 to 4, or 40 to 91.9% by weight of a compound of the general formula (II) 15 where R is a linear or branched alkyl group having a chain length of 8 to 16 carbon atoms and n is equal to 3, and 5 to 50% by weight of a hydrogenated 20 polyisobutylene, of a fully hydrogenated polyisobutylene or of a mixture of a fully hydrogenated and a hydrogenated polyisobutylene.

2. The high-temperature oil as claimed in claim 1, 25 further comprising 0.1 to 6% by weight of an antioxidant.

3. The high-temperature oil as claimed in claim 1 or 2, further comprising 1 to 4% by weight of an 30 antiwear agent. WO 2012/159738 PCT/EP2012/002172 - 28

4. The high-temperature oil as claimed in claims 1 to 3, further comprising 0.1 to 0.5% by weight of an anticorrosive. 5

5. The high-temperature oil as claimed in any of claims 1 to 4, further comprising 0 to 2% by weight of an ionic liquid. 10

6. The high-temperature oil as claimed in any of the preceding claims 1 to 5, wherein the ester compound of the general formula (I) is selected from the group consisting of esters of trimellitic acid, pyromellitic acid, trimesic acid or of a 15 mixture thereof.

7. The high-temperature oil as claimed in any of claims 1 to 5, wherein the compound of the general formula (II) is a derivative of phloroglucinol 20 (benzene-1,3,5-triol).

8. The high-temperature oil as claimed in claim 7, in which the derivative of phloroglucinol is phloroglucinol trioctanoate, phloroglucinol 25 tridecanoate or phloroglucinol tridodecanoate.

9. The high-temperature oil as claimed in any of the preceding claims 1 to 8, wherein the antioxidant bears sulfur and/or nitrogen and/or phosphorus in 30 the molecule, and is selected from the group consisting of aromatic aminic antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldi phenylamine, sterically hindered phenols such as butylhydroxytoluene (BHT), phenolic antioxidants 35 having thioether groups, zinc dialkyldithio phosphates or molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, and WO 2012/159738 PCT/EP2012/002172 - 29 phosphites.

10. The high-temperature oil as claimed in any of the preceding claims 1 to 9, wherein the antiwear 5 agent is selected from the group consisting of antiwear additives based on diphenyl cresyl phosphate, amine-neutralized phosphates, alkylated and nonalkylated triaryl phosphates, alkylated and nonalkylated triaryl thiophosphates, zinc 10 dialkyldithiophosphates or molybdenum dialkyldi thiophosphates or tungsten dialkyldithio phosphates, carbamates, thiocarbamates, zinc dithiocarbamates or molybdenum dithiocarbamates or tungsten dithiocarbamates, dimercaptothiadiazole, 15 calcium sulfonates and benzotriazole derivatives.

11. The high-temperature oil as claimed in any of the preceding claims 1 to 10, wherein the anticorrosive is selected from the group 20 consisting of additives based on overbased calcium sulfonates, amine-neutralized phosphates, alkylated calcium naphthalenesulfonates, oxazoline derivatives, imidazole derivatives, succinic monoesters, N-alkylated benzotriazoles. 25

12. The high-temperature oil as claimed in any of the preceding claims 1 to 11, wherein the ionic liquid is selected from the group consisting of tetraalkylammonium bis(trifluoromethylsulfonyl) 30 imides and tetraalkylphosphonium bis(trifluoro methylsulfonyl)imides, for example trihexyl (tetradecyl)phosphonium bis(trifluoromethyl sulfonyl)imide (HPDimide) and methyltri octylammonium bis(trifluoromethylsulfonyl)imide 35 (Moimide), and tetraalkylammonium tris(perfluoro ethyl) trifluorophosphate and tetraalkylphosphonium tris(perfluoroethyl)trifluorophosphate, especially WO 2012/159738 PCT/EP2012/002172 - 30 tetrabutylphosphonium tris(perfluoroethyl)tri fluorophosphate (BuPPFET), trihexyl(tetradecyl) tris(perfluoroethyl)trifluorophosphate (HDPPFET), pyrrolidinium tris(perfluoroethyl)trifluoro 5 phosphates, tetraalkylammonium, tetraalkyl phosphonium perfluorobutanesulfonates, trihexyl (tetradecyl)phosphonium perfluorobutanesulfonate (HDPnonaflate). 10

13. The use of the high-temperature oil as claimed in any of claims 1 to 12 in the field of industrial chain lubrication in conveying systems, painting lines, the textile industry, the insulating materials industry, the glass industry, and belt 15 lubrication in continuous wood pressing plants used are.