EP0096281B1 - Verfahren zur Herstellung von schwerentflammbaren Flüssigkeiten mit hohem Viskositätsindex und deren Verwendung - Google Patents
Verfahren zur Herstellung von schwerentflammbaren Flüssigkeiten mit hohem Viskositätsindex und deren Verwendung Download PDFInfo
- Publication number
- EP0096281B1 EP0096281B1 EP83105092A EP83105092A EP0096281B1 EP 0096281 B1 EP0096281 B1 EP 0096281B1 EP 83105092 A EP83105092 A EP 83105092A EP 83105092 A EP83105092 A EP 83105092A EP 0096281 B1 EP0096281 B1 EP 0096281B1
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- EP
- European Patent Office
- Prior art keywords
- molecular weight
- phenylene
- weight
- viscosity index
- liquids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000007788 liquid Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 1,2-phenylene, 1,3-phenylene Chemical group 0.000 claims description 18
- 229920000728 polyester Polymers 0.000 claims description 12
- 239000002199 base oil Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000000314 lubricant Substances 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KTFJPMPXSYUEIP-UHFFFAOYSA-N 3-benzoylphthalic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C(O)=O KTFJPMPXSYUEIP-UHFFFAOYSA-N 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 3
- 238000000149 argon plasma sintering Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- OJUZRFGUKHQNJX-UHFFFAOYSA-N (4-methylphenyl) diphenyl phosphate Chemical compound C1=CC(C)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 OJUZRFGUKHQNJX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-N 0.000 description 1
- RSBUDFTVQYJNHK-UHFFFAOYSA-N 1,2,3-trichloro-4-(2,4-dichlorophenoxy)benzene Chemical compound ClC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C(Cl)=C1Cl RSBUDFTVQYJNHK-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- 108010064754 1-ene-dehydrogenase Proteins 0.000 description 1
- GGMPTLAAIUQMIE-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=CC=CC=C1 GGMPTLAAIUQMIE-UHFFFAOYSA-N 0.000 description 1
- HLQDGCWIOSOMDP-UHFFFAOYSA-N 2,3,4,5-tetrachlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=CC(C=2C=CC=CC=2)=C1Cl HLQDGCWIOSOMDP-UHFFFAOYSA-N 0.000 description 1
- IUYHQGMDSZOPDZ-UHFFFAOYSA-N 2,3,4-trichlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=CC=C1C1=CC=CC=C1 IUYHQGMDSZOPDZ-UHFFFAOYSA-N 0.000 description 1
- ZRWRPGGXCSSBAO-UHFFFAOYSA-N 2,4-dichloro-1-(2,4-dichlorophenoxy)benzene Chemical compound ClC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl ZRWRPGGXCSSBAO-UHFFFAOYSA-N 0.000 description 1
- PIORTDHJOLELKR-UHFFFAOYSA-N 2,4-dichloro-1-(4-chlorophenoxy)benzene Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl PIORTDHJOLELKR-UHFFFAOYSA-N 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001374 small-angle light scattering Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
- C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
- C10M105/54—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen, halogen and oxygen
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
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- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/22—Polyesters
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- C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
- C10M151/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/102—Polyesters
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/003—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions used as base material
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/0206—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only used as base material
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
- C10M2211/0225—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic used as base material
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
- C10M2211/0245—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic used as base material
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/0406—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen used as base material
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
- C10M2211/0425—Alcohols; Ethers; Aldehydes; Ketones used as base material
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/044—Acids; Salts or esters thereof
- C10M2211/0445—Acids; Salts or esters thereof used as base material
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- C10M2211/06—Perfluorinated compounds
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- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/043—Polyoxyalkylene ethers with a thioether group
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/003—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/023—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/0405—Phosphate esters used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/049—Phosphite
- C10M2223/0495—Phosphite used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/0603—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/08—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-nitrogen bonds
- C10M2223/083—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-nitrogen bonds used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/10—Phosphatides, e.g. lecithin, cephalin
- C10M2223/103—Phosphatides, e.g. lecithin, cephalin used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- the invention relates to a method for producing flame-retardant liquids with a high viscosity index and their use as hydraulic fluids and / or as heat transfer fluids.
- Phosphate esters or polychlorinated aromatics which can be used for HSD hydraulic oils, do not pose any corrosion problems because they are water-free and do not cause high wear at highly stressed friction points.
- the widespread use of these two product classes is mainly hampered by their extraordinarily poor viscosity-temperature behavior.
- the viscosities of the triaryl phosphates and low chlorinated aromatics which are not particularly thermally stable, are too low for the above-mentioned uses.
- Known viscosity index improvers such as e.g. B. Polymethacrylates and polyolefin copolymers are known as thickening substances that also raise the viscosity index of this liquid sufficiently, but they lose considerable effectiveness at high shear rates at lubrication points.
- the object of the invention is therefore that special polymers are added to the synthetic base oil, which have a favorable influence on their viscosity properties, without appreciably affecting the flame resistance and shear stability and are well compatible with the base oil.
- the weight-average molecular weight, M W is determined here using the laser small-angle light scattering method.
- the synthetic base oil is mixed with the higher molecular weight polyester.
- This can be prepared by a polycondensation reaction from an aromatic or (cyclo) aliphatic dicarboxylic acid or a suitable aromatic or (cyclo) aliphatic dicarboxylic acid derivative and a polytetramethylene glycol according to known processes (WK Witsiepe, Advan. Chem. Ser; 1973, 129, 39-60).
- High molecular weight polyesters are used to produce the liquids according to the invention. These are derivatives based on aromatic dicarboxylic acids, e.g. B. phthalic acid, isophthalic acid, terephthalic acid, naphthalic acid, naphthalenedicarboxylic acid 1,4, naphthalenedicarboxylic acid 1,5, diphenyl dicarboxylic acid 3,4, diphenyl dicarboxylic acid 2,2 ', diphenyl dicarboxylic acid 4,4, benzophenone dicarboxylic acid -3,4, benzophenone dicarboxylic acid 2,2 ', benzophenone dicarboxylic acid 2,2', benzophenone dicarboxylic acid 4,4 ', diphenyl ether dicarboxylic acid 3,4, diphenyl ether dicarboxylic acid 2,2', diphenyl ether -dicarboxylic acid-4,4 ', diphenyl sulfide-dicarboxylic
- Phthalic acid, isophthalic acid and terephthalic acid are preferred. Terephthalic acid is particularly preferred.
- the liquids according to the invention can furthermore contain customary further additives, for example antioxidants (for example 2,6 di-tert-butyl-p-cresol, 2,2 'methylene-bis- (4-methyl) -6-tert.- butylphenol etc.), stabilizers (e.g. carbodiimides), antiwear additives (e.g. zinc alkyldithiophosphates), foam-suppressing additives, corrosion inhibitors.
- antioxidants for example 2,6 di-tert-butyl-p-cresol, 2,2 'methylene-bis- (4-methyl) -6-tert.- butylphenol etc.
- stabilizers e.g. carbodiimides
- antiwear additives e.g. zinc alkyldithiophosphates
- foam-suppressing additives e.g. zinc alkyldithiophosphates
- corrosion inhibitors for example 2,6 di-tert-butyl-p-cresol, 2,2 'm
- Diols for example commercially available polytetramethylene glycols such as “Polymeg®” (Quaker Oats) or Teracol ”(Du Pont), are used as alcohol components to produce the polyester products according to the invention.
- Polymeg® Quaker Oats
- Teracol Teracol
- polytetramethylene glycols with an average molecular weight of 360-10,000 (calculated from the hydroxyl number), preferably from 650-5,000 and particularly preferably from 860-3,600, are chosen.
- the choice of catalyst depends on the dicarboxylic acid derivative used.
- the molar ratio of dicarboxylic acid derivatives to alcohol component is generally 1: 1.
- Suitable synthetic base oils are: aromatic phosphates such as tricresyl phosphate, dicresyl monophenyl phosphate. Monocresyl diphenyl phosphate and other phosphate esters of monophenols. Chlorinated aromatic compounds such as trichlorobiphenyl, tetrachlorobiphenyl, pentachlorobiphenyl, trichlorodiphenyl ether and tetrachlorodiphenyl ether can also be used. Pentachlorodiphenyl ether etc. can be used as base oils.
- the flame-retardant liquids according to the invention consisting of a base oil and A higher molecular weight polyester can be used as a lubricant, lubricant additives in general. They can also be used as hydraulic fluids.
- Table 1 clearly shows the superior thickening effect and the viscosity index-increasing effect.
- Table 2 shows the results of shear tests based on DIN 51 382. The good shear strength of the liquids according to the invention can be seen from this. (See table 2 page 6 f.)
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
Description
- Die Erfindung betrifft ein Verfahren zur Herstellung von schwerentflammbaren Flüssigkeiten mit hohem Viskositätsindex und deren Verwendung als Hydraulikflüssigkeiten und/oder als Wärmeträgerflüssigkeiten.
- Folgende Arten von schwerentflammbaren Hydraulikflüssigkeiten sind bekannt und werden in dem 5. Luxemburger Bericht über die Anforderungen und Prüfung schwerentflammbarer Flüssigkeiten zur hydraulischen Kraftübertragung und Steuerung (1974) definiert :
- HSA : ÖI-in-Wasser-Emulsionen mit einem brennbaren Anteil von höchstens 20 %. Betriebstemp. von + 5 bis + 55 °C.
- HSB : Wasser-in-ÖI-Emulsionen mit einem brennbaren Anteil von höchstens 60 %. Betriebstemp. von + 5 bis + 60 °C.
- HSC : Wäßrige Polymerlösungen mit mindestens 35 % Wasser. Betriebstemp. von - 20 bis + 60 °C.
- HSD : Wasserfreie Flüssigkeiten. Betriebstemp. von - 20 bis + 150 °C.
- Die Typen HSA, HSB und HSC enthalten unterschiedliche Mengen Wasser. Dies kann Probleme in Bezug auf ausreichenden Korrosionsschutz ergeben. Weiterhin können mit diesen Hydraulikflüssigkeiten betriebene Systeme an hochbelasteten Reibstellen einem erhöhten Verschleiß ausgesetzt sein. Daneben besteht die Gefahr einer Kontamination mit Mikroorganismen, wodurch die Produkteigenschaften schlechter werden können (Ullmanns Encyklopädie der technischen Chemie, Band 13, S. 92-94, Verlag Chemie, Weinheim, New York, 4. Auflage, 1977).
- Phosphatester oder polychlorierte Aromaten, die für HSD-Hydrauliköle eingesetzt werden können, stellen keine Korrosionsprobleme, da sie wasserfrei sind, und bewirken keinen hohen Verschleiß an hochbelasteten Reibstellen. Einer breiten Anwendung dieser beiden Produktklassen steht jedoch hauptsächlich deren außerordentlich schlechtes Viskositäts-Temperatur-Verhalten entgegen.
- Weiterhin sind die Viskositäten der thermisch wenig belastbaren Triarylphosphate und niedrig chlorierten Aromaten für die oben genannten Verwendungszwecke zu niedrig. Bekannte Viskositätsindexverbesserer wie z. B. Polymethacrylate und Polyolefincopolymere sind zwar als verdickend wirkende Substanzen bekannt, die auch den Viskositätsindex dieser Flüssigkeit ausreichend anheben, sie verlieren aber bei hohen Schergefällen an Schmierstellen beträchtlich an Wirksamkeit.
- Die Aufgabe der Erfindung besteht daher darin, daß spezielle Polymere dem synthetischen Basisöl zugesetzt werden, die deren Viskositätseigenschaften günstig beeinflussen, ohne die Flammfestigkeit und Scherstabilität nennenswert zu beeinträchtigen und mit dem Basisöl gut verträglich sind.
- Von den marktgängigen Verbindungen, die die Viskosität von Schmierölen günstig beeinflussen, kommen nur polare Verbindungen, beispielsweise polymethacrylate in Frage. Um die gewünschten Verbesserungen der Viskositätseigenschaften zu erzielen, müßten höher molekulare Polymethacrylate verwendet werden. Dies kann die Scherstabilität ungünstig beeinflussen. Niedermolekulare Polymethacrylate beeinflussen zwar die Scherstabilität weniger, eignen sich dafür aber bei niedriger Dosierung weniger gut zur Verbesserung der Viskositätseigenschaften.
- Es wurde nun gefunden, daß Mischungen aus einem hochflammfesten Basisöl und einem höhermolekularen Polyester Viskositäts- und Schereigenschaften aufweisen, die den oben genannten Erfordernissen genügen.
- Gegenstand der Erfindung ist daher ein Verfahren zur Herstellung von schwerentflammbaren Flüssigkeiten mit hohem Viskositätsindex, das dadurch gekennzeichnet ist, daß 96-99.9 Gew.-% eines hochflammfesten Basisöls, das aromatische Strukturen enthält und 0.1-4 Gew.-% eines höher molekularen Polyesters der Formel I
in welcher - Y einen 1,2-Phenylen-, 1,3-Phenylen-, 1,4-Phenylenrest oder einen Rest der Formel
bedeutet, - n eine ganze Zahl von 5 bis 140 bedeutet und
- x für eine solche Zahl steht, daß das gewichtsgemittelte Molekulargewicht einen Wert von 20 000 bis 300 000 ergibt,
- Bevorzugt sind höhermolekulare Polyester, in denen Y für Phenylenreste oder Cycloalkylengruppen und n für eine Zahl von 9-70 steht und mit einer solchen Zahl x, daß das gewichtsgemittelte Molekulargewicht des Polymeren einen Wert zwischen 30 000 und 200 000 annimmt.
- Besonders bevorzugt sind höhermolekulare Polyester mit Y = 1,4-Phenylen, mit n = 12-50 und mit einer solchen Zahl x, daß das gewichtsgemittelte Molekulargewicht des Polymeren einen Wert von 40 000 bis 150 000 annimmt.
- Das gewichtsgemittelte Molekulargewicht, MW, wird hierbei mit dem Laserkleinwinkellichtstreuungs-Verfahren bestimmt.
- Diese neuen Polyester wirken ausreichend verdickend, sind bei hohen Schergefällen stabil und erhöhen die Schmierfilmtragfähigkeiten.
- Zur Herstellung der erfindungsgemäßen schwerentflammbaren Flüssigkeiten vermischt man das synthetische Basisöl mit dem höhermolekularen Polyester. Dieser kann durch eine Polykondensationsreaktion aus einer aromatischen bzw. (cyclo)aliphatischen Dicarbonsäure bzw. einem geeigneten aromatischen bzw. (cyclo)aliphatischen Dicarbonsäurederivat und einem Polytetramethylenglykol nach bekannten Verfahren, hergestellt werden (W. K. Witsiepe, Advan. Chem. Ser; 1973, 129, 39-60).
- Zur Herstellung der erfindungsgemäßen Flüssigkeiten werden höhermolekulare Polyester verwendet. Diese sind Derivate auf der Basis von aromatischen Dicarbonsäuren, z. B. Phthalsäure, Isophthalsäure, Terephthalsäure, Naphthalsäure, Naphthalindicarbonsäure-1,4, Naphthalindicarbonsäure-1,5, Diphenyl-dicarbonsäure-3,4, Diphenyl-dicarbonsäure-2,2', Diphenyl-dicarbonsäure-4,4, Benzophenon-dicarbonsäure-3,4, Benzophenon-dicarbonsäure-2,2', Benzophenon-dicarbonsäure-2,2', Benzophenon-dicarbonsäure-4,4', Diphenylether-dicarbonsäure-3,4, Diphenylether-dicarbonsäure-2,2', Diphenylether-dicarbonsäure-4,4', Diphenylsulfid-dicarbonsäure-3,4, Diphenylsulfid-dicarbonsäure-2,2', Diphenylsulfid-dicarbonsäure-4,4', Diphenylsulfon-dicarbonsäure-3,4, Diphenylsulfon-dicarbonsäure-2,2', Diphenylsulfon-dicarbonsäure-4,4' usw. Weiterhin werden reaktionsfähige Derivate dieser Säuren, z. B. Carbonsäureanhydride, Carbonsäurehalogenide, Ester niedermolekularer Monoalkohole oder Monophenole, Acylimidazole verwendet.
- Bevorzugt sind Phthalsäure, Isophthalsäure und Terephthalsäure. Besonders bevorzugt ist Terephthalsäure.
- Von den Derivaten auf Basis von Dicarbonsäuren werden vorzugsweise die Dimethylester verwendet. Weiterhin können die erfindungsgemäßen Flüssigkeiten übliche weitere Zusätze enthalten, beispielsweise Antioxidantien (z. B. 2,6 Di-tert.-butyl-p-kresol, 2,2' Methylen-bis-(4-methyl)-6-tert.-butylphenol usw.), Stabilisatoren (z. B. Carbodiimide), Antiwearadditive (z. B. Zink-Alkyldithiophosphate), schaumdämpfende Additive, Korrosionsinhibitoren.
- Zur Herstellung der erfindungsgemäßen Polyesterprodukte werden als Alkoholkomponente Diole verwendet, beispielsweise handelsübliche Polytetramethylenglykole wie « Polymeg® » (Quaker Oats) oder Teracol" (Du Pont).
- Zur Herstellung der erfindungsgemäßen höhermolekularen Polyester wählt man Polytetramethylenglykole mit einem mittleren Molekulargewicht von 360-10 000 (berechnet aus der Hydroxylzahl), bevorzugt von 650-5 000 und besonders bevorzugt von 860-3 600.
- Die Katalysatorwahl hängt vom eingesetzten Dicarbonsäurederivat ab. Vorzugsweise werden Niedrigalkyltitansäureester, Bis(niedrigalkyl)zinnoxide oder Zinn(II)-salze von aliphatischen C2-C2O-Monocarbonsäuren als Katalysator verwendet.
- Das Molverhältnis Dicarbonsäurederivate zu Alkoholkomponente beträgt im allgemeinen 1 : 1.
- Als synthetische Basisöle kommen beispielsweise in Frage : aromatische Phosphate wie Trikresylphosphat, Dikresylmonophenylphosphat. Monokresyldiphenyl-phosphat und andere Phosphatester von Monophenolen. Weiterhin können chlorierte aromatische Verbindungen wie Trichlor-biphenyl, Tetrachlor-biphenyl, Pentachlor-biphenyl, Trichlor-diphenylether, Tetrachlordiphenylether. Pentachlor-diphenylether usw. als Basisöle verwendet werden.
- Die erfindungsgemäßen schwerentflammbaren Flüssigkeiten, bestehend aus einem Basisöl und einem höhermolekularen Polyester können als Schmiermittel, Schmiermittelzusätze allgemein verwendet werden. Weiterhin können sie als Hydraulikflüssigkeiten eingesetzt werden.
- In einem ölbeheizten gerührten 20-I-Autoklaven werden 7 710 g eines Polytetramethylenglykols mit einem mittleren Molekulargewicht von 1000 (Polymeg® 1000), 1 500 g Dimethylterephthalat und 2,6 g Tetra-n-butyl-titanat unter Stickstoff bei 190°C 2 Stunden (150 U/min. Rührerumdrehungsgeschwindigkeit) gerührt. Danach wird die Temperatur für 1 Stunde auf 200 °C erhöht. Im Verlauf von 90 Min. wird anschließend der Druck (Normaldruck) bis auf etwa 1 mbar langsam gesenkt und gleichzeitig die Rührerdrehzahl auf 50 U/min. erniedrigt. Nach weiteren 30 Min. Laufzeit bei 1 mbar wird die Umsetzung beendet, und nach dem Belüften wird das Umsetzungsprodukt abgelassen. Farblose, sehr hochviskose, transparente Masse.
M w (Lichtstreuung) : 79 000. - Analog dem Beispiel 1 werden 9115 g eines Polytetramethylenglykols mit einem mittleren Molekulargewicht von 2000 (Polymeg" 2000), 885 g Dimethylterephthalat und 2,8 g Tetra-n-butyl-titanat polykondensiert. Farblose, sehr hochviskose, transparente Masse, die bei längerem Stehen bei Raumtemperatur farblos erstarrt.
- Mw (Lichtstreuung) : 78 000
-
M n (ber. aus der Ausbeute des Destillats) : 50 000. - 329 g einer handelsüblichen hydrierten Dimerfettsäure (Empol® 1010 ; Unilever Emery), 1 171 g eines Polytetramethylenglykols mit einem mittleren Molekulargewicht von 2000 (Polymeg® 2000), 3,3 g Tetra-n-butyl-titanat und 600 g Toluol werden vermischt und unter Stickstoff bei Normaldruck 36 Stunden am Wasserabscheider unter Rückfluß gekocht (Säurezahl vor Umsetzung 37,4, nach Umsetzung 3,0 mg KOH/g). Das farblose, sehr hochviskose, transparente Produkt wird im Vakuum von Toluol befreit.
-
M w (Lichtstreuung) : 34 700. -
- Aus der Tabelle 1 geht klardie überlegene Aufdickwirkung und der Viskositätsindex-erhöhende Effekt hervor.
-
miteinander gemischt werden.
Claims (3)
miteinander gemischt werden.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3221137 | 1982-06-04 | ||
| DE19823221137 DE3221137A1 (de) | 1982-06-04 | 1982-06-04 | Verfahren zur herstellung von schwerentflammbaren fluessigkeiten mit hohem viskositaetsindex und deren verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0096281A2 EP0096281A2 (de) | 1983-12-21 |
| EP0096281A3 EP0096281A3 (en) | 1985-05-15 |
| EP0096281B1 true EP0096281B1 (de) | 1987-07-29 |
Family
ID=6165348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP83105092A Expired EP0096281B1 (de) | 1982-06-04 | 1983-05-24 | Verfahren zur Herstellung von schwerentflammbaren Flüssigkeiten mit hohem Viskositätsindex und deren Verwendung |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4490266A (de) |
| EP (1) | EP0096281B1 (de) |
| DE (2) | DE3221137A1 (de) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2020299B3 (es) * | 1986-12-19 | 1991-08-01 | Ciba-Geigy Ag | Resinas epoxidicas con contenido de poliester sobre base de polialquilenglicol. |
| US5066409A (en) * | 1990-09-12 | 1991-11-19 | The Dow Chemical Company | Novel aryl ether sulfones |
| US5128067A (en) * | 1991-12-19 | 1992-07-07 | Fmc Corporation | Fire resistant low temperature grease |
| CA2136427C (en) * | 1993-03-25 | 2003-07-15 | Asahi Denka Kogyo K. K. | A lubricant for use in refrigerators and a refrigerant composition using same |
| DE4435548A1 (de) * | 1994-10-05 | 1996-04-11 | Rhein Chemie Rheinau Gmbh | Stabilisierte Schmierstoff-Grundsubstanz |
| US5494595A (en) | 1994-12-30 | 1996-02-27 | Huntsman Corporation | Oil soluble polyethers |
| US5783528A (en) * | 1997-01-07 | 1998-07-21 | Diversey Lever, Inc. | Synthetic lubricant based on enhanced performance of synthetic ester fluids |
| CN110088256B (zh) * | 2016-12-14 | 2022-04-29 | 赢创运营有限公司 | 聚酯作为飞机液压流体的粘度指数改进剂的用途 |
| JP7471022B1 (ja) * | 2023-04-28 | 2024-04-19 | 築野グループ株式会社 | 二塩基酸とポリオキシアルキレングリコールとのエステル |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE567232A (de) * | 1957-04-30 | |||
| US3867298A (en) * | 1971-02-19 | 1975-02-18 | Ethyl Corp | Lubricant |
| US3935116A (en) * | 1972-02-28 | 1976-01-27 | Mcdonnell Douglas Corporation | Functional fluid compositions |
| US3951837A (en) * | 1973-09-24 | 1976-04-20 | Mcdonnell Douglas Corporation | Functional fluid compositions |
| US3956154A (en) * | 1974-02-11 | 1976-05-11 | Stauffer Chemical Company | Hydraulic fluid system |
| JPS53105677A (en) * | 1977-02-25 | 1978-09-13 | Kao Corp | Flame retardant working oil composite and manufacturing method thereof |
-
1982
- 1982-06-04 DE DE19823221137 patent/DE3221137A1/de not_active Withdrawn
-
1983
- 1983-05-24 US US06/497,529 patent/US4490266A/en not_active Expired - Fee Related
- 1983-05-24 DE DE8383105092T patent/DE3372782D1/de not_active Expired
- 1983-05-24 EP EP83105092A patent/EP0096281B1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3221137A1 (de) | 1983-12-08 |
| EP0096281A2 (de) | 1983-12-21 |
| US4490266A (en) | 1984-12-25 |
| EP0096281A3 (en) | 1985-05-15 |
| DE3372782D1 (en) | 1987-09-03 |
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