EP0184713A2 - Lubrifiants stabilisés à base de polyéther - Google Patents

Lubrifiants stabilisés à base de polyéther Download PDF

Info

Publication number: EP0184713A2
Authority: EP; European Patent Office
Prior art keywords: alkyl; bis; cycloalkyl; group; oder
Prior art date: 1984-12-08
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP85114960A

Other languages

German (de)

English (en)

Other versions

EP0184713A3 (fr

Inventor

Hans-Josef Dr. Buysch

Siegfried Dipl.-Ing. Kussi

Günther Dr. Boehmke

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1984-12-08

Filing date

1985-11-26

Publication date

1986-06-18

1985-11-26 Application filed by Bayer AG filed Critical Bayer AG

1986-06-18 Publication of EP0184713A2 publication Critical patent/EP0184713A2/fr

1987-02-04 Publication of EP0184713A3 publication Critical patent/EP0184713A3/fr

Status Withdrawn legal-status Critical Current

Links

239000000314 lubricant Substances 0.000 title claims abstract description 36
229920000570 polyether Polymers 0.000 title claims abstract description 36
239000004721 Polyphenylene oxide Substances 0.000 title description 23
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 15
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
150000002431 hydrogen Chemical class 0.000 claims abstract description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
235000007586 terpenes Nutrition 0.000 claims abstract description 12
230000001588 bifunctional effect Effects 0.000 claims abstract description 9
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
150000003505 terpenes Chemical class 0.000 claims abstract description 8
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 24
239000003381 stabilizer Substances 0.000 claims description 23
-1 α-methylstyryl Chemical group 0.000 claims description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
229920000642 polymer Polymers 0.000 claims description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
239000006078 metal deactivator Substances 0.000 claims description 5
239000003921 oil Substances 0.000 claims description 5
125000005504 styryl group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
150000004982 aromatic amines Chemical class 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
238000005260 corrosion Methods 0.000 claims description 2
230000007797 corrosion Effects 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
239000002530 phenolic antioxidant Substances 0.000 claims description 2
239000011814 protection agent Substances 0.000 claims description 2
BPELEZSCHIEMAE-UHFFFAOYSA-N salicylaldehyde imine Chemical compound OC1=CC=CC=C1C=N BPELEZSCHIEMAE-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
150000002118 epoxides Chemical class 0.000 claims 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
239000000654 additive Substances 0.000 abstract description 9
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 8
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 10
238000009472 formulation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000010687 lubricating oil Substances 0.000 description 4
230000006641 stabilisation Effects 0.000 description 4
238000011105 stabilization Methods 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
XQVWYOYUZDUNRW-UHFFFAOYSA-N N-phenyl-alpha-naphthylamine Natural products C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012530 fluid Substances 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
AIMXDOGPMWDCDF-UHFFFAOYSA-N 1-n,4-n-dicyclohexylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1CCCCC1 AIMXDOGPMWDCDF-UHFFFAOYSA-N 0.000 description 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
AKNMPWVTPUHKCG-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(C2CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1CCCCC1 AKNMPWVTPUHKCG-UHFFFAOYSA-N 0.000 description 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000007857 degradation product Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000003014 phosphoric acid esters Chemical class 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
230000002195 synergetic effect Effects 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
SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 description 1
MQWCQFCZUNBTCM-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenyl)sulfanyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(SC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O MQWCQFCZUNBTCM-UHFFFAOYSA-N 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
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012208 gear oil Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000001976 improved effect Effects 0.000 description 1
UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000005555 metalworking Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
GLZWNFNQMJAZGY-UHFFFAOYSA-N octaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCO GLZWNFNQMJAZGY-UHFFFAOYSA-N 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
239000000123 paper Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
239000003566 sealing material Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
239000004753 textile Substances 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- 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
- C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
- 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
- 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
- C10M145/24—Polyethers
- C10M145/26—Polyoxyalkylenes
- C10M145/36—Polyoxyalkylenes etherified
- 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
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
- 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
- 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
- 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
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
- 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
- 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
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
- 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
- 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
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
- 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
- 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
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
- 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
- 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
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
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- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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- C10M2215/30—Heterocyclic compounds
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- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/041—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving a condensation reaction
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- C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C—CHEMISTRY; METALLURGY
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- C10M2219/089—Overbased salts
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- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
- C—CHEMISTRY; METALLURGY
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- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
- C—CHEMISTRY; METALLURGY
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- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- 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
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- 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
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties

Definitions

the present invention relates to polyether-based lubricants stabilized with special diphenylamine derivatives.
Polyether-based lubricants are known. They are characterized by excellent lubricity, good viscosity behavior, high flash point, low volatility, low pour point and low impact on metals and sealing materials. They can be used over a wide temperature range, for example from -20 to + 220 ° C. Because of these properties, lubricants based on polyether are used in particular as hydraulic fluids, brake fluids, metalworking fluids, lubricants for compressors and refrigeration machines and as bearing and gear oils for thermally and mechanically highly stressed units in the paper, textile and plastics industries.
polyether-based lubricants often have insufficient thermal and oxidation stability and therefore do not always meet all the requirements placed on high-quality lubricants.
additives In order to improve the properties of lubricants based on polyethers, additives have already been proposed, such as aromatic amines, e.g. Phenyl-ctnaphthylamine, phenothiazine derivatives and certain diphenylamine derivatives (see Ullmann's Encyclopedia of Industrial Chemistry, 4th edition, volume 20, page 510, DE-OS 22 11 805 and DE-OS 28 06 133).
aromatic amines e.g. Phenyl-ctnaphthylamine, phenothiazine derivatives and certain diphenylamine derivatives
Such polyethers are generally oils which have molecular weights of, for example, 500 to 20,000. They preferably have molar masses of 1000 to 7000. They can be prepared by methods known per se, for example by an alkali-catalyzed or acid-catalyzed polymerization of the cyclic ethers, it being possible to use monoalcohols, polyalcohols or amines as starter molecules.
the OH end groups of the polyethers thus produced can be closed by a conventional alkylation or acylation, i.e. be converted into ether or ester end groups.
Polyethers which are particularly suitable for the stabilization according to the invention are oils with molecular weights of 500 to 20,000, preferably with molecular weights of 1,500 to 7,000, which are obtained by alkali-catalyzed addition of propylene oxide and optionally ethylene oxide to alcohols, for example ethanol, butanol, propanediol, glycerol, trimethylolpropane or Pentaerythritol.
the diphenylamine derivatives of the formula (VII) can be present, for example, in amounts of 0 to 10% by weight, based on the mixture. This amount is preferably 0.1 to 5% by weight.
the metal deactivators of the formula (VIII) can be present, for example, in an amount of 0 to 4% by weight, based on the mixture. This amount is preferably 0.5 to 2% by weight.
the other additives can, for example, each be present in amounts of 0 to 10% by weight, based on the mixture. This amount is preferably 0 to 5% by weight.
the lubricants according to the invention can be produced in various ways.
diphenylamine derivatives of the formula (I) and, if appropriate, further additives can be added to polyethers in the desired proportions and, if appropriate with heating, for example at 80 to 100 ° C., dissolved therein.
Another possibility is to first produce concentrates from the stabilizers using a suitable medium and to add these to the polyether lubricant to be stabilized in accordance with the desired proportions.
suitable concentrations for Such concentrates are, for example, those from 20 to 90% by weight, suitable media for their production are, for example, higher alcohols, such as 2-ethylhexanol and octaethylene glycol, but especially polyether lubricants. You can also mix the stabilizers or their concentrates first in the desired proportions and add this mixture to the lubricant to be stabilized.
a commercial polypropylene ether with a molecular weight of 5500 and started on trimethylolpropane was mixed with 2% by weight, based on the mixture, of the specified stabilizers and the mixture was tested for oxidation stability in accordance with DIN 51 352 Part 2.
the oil to be tested was aged in a glass vessel with 0.1% by weight of ferric oxide as a catalyst while introducing 15 l / h of air at 200 ° C. for 24 hours.
the viscosity of the aged samples was determined at 40 ° C. and compared with the viscosity of the non-aged sample.
Table 1 shows the stabilizers tested, and Table 2 the results obtained.
the (kinetic) viscosity measurements were carried out in accordance with DIN 51562, Part 1 (Ubbelohde method).
Table 4 shows good resistance to degradation for all products at the lower temperatures and short exposure times. At higher temperatures and especially with long exposure times, the formulations according to the invention prove to be significantly more stable. Also noteworthy is the low or even constant loss of evaporation of samples A and B over a period of 3 hours with increasing temperatures.
the amount of stabilizer applied is significantly less than in comparative experiment C.

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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)
Lubricants (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

EP85114960A 1984-12-08 1985-11-26 Lubrifiants stabilisés à base de polyéther Withdrawn EP0184713A3 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3444884		1984-12-08
DE3444884A DE3444884A1 (de)	1984-12-08	1984-12-08	Stabilisierte schmierstoffe auf der basis von polyethern

Publications (2)

Publication Number	Publication Date
EP0184713A2 true EP0184713A2 (fr)	1986-06-18
EP0184713A3 EP0184713A3 (fr)	1987-02-04

Family

ID=6252293

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP85114960A Withdrawn EP0184713A3 (fr)	1984-12-08	1985-11-26	Lubrifiants stabilisés à base de polyéther

Country Status (6)

Country	Link
US (1)	US4627929A (fr)
EP (1)	EP0184713A3 (fr)
JP (1)	JPS61138696A (fr)
BR (1)	BR8506132A (fr)
DE (1)	DE3444884A1 (fr)
ES (1)	ES8705510A1 (fr)

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US6797677B2 (en)	2002-05-30	2004-09-28	Afton Chemical Corporation	Antioxidant combination for oxidation and deposit control in lubricants containing molybdenum and alkylated phenothiazine
US8202829B2 (en) *	2004-11-04	2012-06-19	Afton Chemical Corporation	Lubricating composition
CN103842488A (zh) *	2011-03-29	2014-06-04	陶氏环球技术有限责任公司	包含低Noack挥发度的聚烷撑二醇二醚的润滑剂组合物
US10260017B2 (en)	2015-12-22	2019-04-16	Eastman Chemical Company	Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including said compounds
US10287418B2 (en) *	2015-12-22	2019-05-14	Eastman Chemical Company	Compounds with antidegradant and antifatigue efficacy and compositions including said compounds
US10167252B2 (en) *	2015-12-22	2019-01-01	Eastman Chemical Company	Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including such compounds
US10160718B2 (en) *	2015-12-22	2018-12-25	Eastman Chemical Company	Methods of making compounds having antidegradant and antifatigue efficacy
US10428009B2 (en)	2015-12-22	2019-10-01	Eastman Chemical Company	Methods of making compounds and mixtures having antidegradant and antifatigue efficacy
EP3634939B1 (fr) *	2017-06-09	2021-03-24	Eastman Chemical Company	Procédés de fabrication de composés ayant un effet protecteur et une efficacité anti-fatigue
MX2021003642A (es) *	2018-11-14	2021-05-27	Sika Tech Ag	Composicion curable para sustratos alcalinos.

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CA560340A (fr) *		1958-07-15	H. Matuszak Alfred	Melanges de lubrifiant d'ester synthetique inhibe
US2848444A (en) *	1955-05-25	1958-08-19	Exxon Research Engineering Co	Diphenylamine-metal polysulfide reaction products and method of preparing same
US2930758A (en) *	1956-09-28	1960-03-29	Texaco Inc	Ester-base lubricant containing anti-oxidant mixtures
US3282840A (en) *	1962-11-29	1966-11-01	Eastman Kodak Co	Stable lubricating composition and inhibitor mixture therefor
GB1053062A (fr) *	1963-04-30
US3696851A (en) *	1964-02-11	1972-10-10	Geigy Chem Corp	Chemical compounds and compositions
US4110234A (en) *	1975-11-05	1978-08-29	Uniroyal, Inc.	Antioxidant stabilized lubricating oils
US4119551A (en) *	1977-06-28	1978-10-10	Texaco Inc.	Synthetic aircraft turbine lubricating oil compositions
DE2806133C2 (de) *	1978-02-14	1987-03-26	Hoechst Ag, 6230 Frankfurt	Verwendung von Polyoxyalkylenglykoldiethern für die Bereitung von Getriebeölen
DE3127750A1 (de) *	1981-07-14	1983-02-03	Bayer Ag, 5090 Leverkusen	Stabilisatorhaltige reaktivkomponenten fuer pu-schaumstoffe, neue stabilisatoren und ein verfahren zur herstellung der stabilisatoren

1984
- 1984-12-08 DE DE3444884A patent/DE3444884A1/de not_active Withdrawn
1985
- 1985-11-26 EP EP85114960A patent/EP0184713A3/fr not_active Withdrawn
- 1985-12-02 US US06/803,458 patent/US4627929A/en not_active Expired - Fee Related
- 1985-12-03 JP JP60270846A patent/JPS61138696A/ja active Pending
- 1985-12-06 ES ES549665A patent/ES8705510A1/es not_active Expired
- 1985-12-06 BR BR8506132A patent/BR8506132A/pt unknown

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Publication number	Publication date
ES549665A0 (es)	1987-05-01
JPS61138696A (ja)	1986-06-26
US4627929A (en)	1986-12-09
ES8705510A1 (es)	1987-05-01
DE3444884A1 (de)	1986-06-12
EP0184713A3 (fr)	1987-02-04
BR8506132A (pt)	1986-08-26

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