EP3074489A1 - Verwendung von polyalkylenglykolestern in schmierölzusammensetzungen - Google Patents
Verwendung von polyalkylenglykolestern in schmierölzusammensetzungenInfo
- Publication number
- EP3074489A1 EP3074489A1 EP14798865.3A EP14798865A EP3074489A1 EP 3074489 A1 EP3074489 A1 EP 3074489A1 EP 14798865 A EP14798865 A EP 14798865A EP 3074489 A1 EP3074489 A1 EP 3074489A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- range
- acid
- polyalkylene glycol
- general formula
- integer
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 89
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 47
- 229920001515 polyalkylene glycol Polymers 0.000 title claims abstract description 46
- 150000002334 glycols Chemical class 0.000 title description 27
- 239000002253 acid Substances 0.000 claims abstract description 37
- 150000002148 esters Chemical class 0.000 claims abstract description 35
- 239000000314 lubricant Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 15
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 238000005461 lubrication Methods 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 4
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 229920000909 polytetrahydrofuran Polymers 0.000 abstract description 3
- -1 defoamers Substances 0.000 description 64
- 239000002270 dispersing agent Substances 0.000 description 56
- 239000003921 oil Substances 0.000 description 44
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 21
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 229940067631 phospholipid Drugs 0.000 description 16
- 150000003904 phospholipids Chemical class 0.000 description 16
- 229920013639 polyalphaolefin Polymers 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 229960002317 succinimide Drugs 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- 239000012530 fluid Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 230000001050 lubricating effect Effects 0.000 description 8
- 239000004034 viscosity adjusting agent Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 7
- 150000001733 carboxylic acid esters Chemical class 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 239000005864 Sulphur Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 235000010338 boric acid Nutrition 0.000 description 6
- 229960002645 boric acid Drugs 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 230000007306 turnover Effects 0.000 description 6
- 239000004711 α-olefin Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229920002367 Polyisobutene Polymers 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 150000001639 boron compounds Chemical class 0.000 description 5
- 239000010725 compressor oil Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000005555 metalworking Methods 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 239000010705 motor oil Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 239000006078 metal deactivator Substances 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Chemical class 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920001748 polybutylene Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- QJRRBVNPIKYRQJ-UHFFFAOYSA-N 10-methylundecanoic acid Chemical compound CC(C)CCCCCCCCC(O)=O QJRRBVNPIKYRQJ-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 description 2
- 229910011255 B2O3 Inorganic materials 0.000 description 2
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- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
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- 150000002989 phenols Chemical class 0.000 description 1
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- 150000008301 phosphite esters Chemical class 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 238000012345 traction test Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- IRKHIJIMXUBALO-UHFFFAOYSA-N triheptyl borate Chemical compound CCCCCCCOB(OCCCCCCC)OCCCCCCC IRKHIJIMXUBALO-UHFFFAOYSA-N 0.000 description 1
- KDQYHGMMZKMQAA-UHFFFAOYSA-N trihexyl borate Chemical compound CCCCCCOB(OCCCCCC)OCCCCCC KDQYHGMMZKMQAA-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AZLXEMARTGQBEN-UHFFFAOYSA-N trinonyl borate Chemical compound CCCCCCCCCOB(OCCCCCCCCC)OCCCCCCCCC AZLXEMARTGQBEN-UHFFFAOYSA-N 0.000 description 1
- DTBRTYHFHGNZFX-UHFFFAOYSA-N trioctyl borate Chemical compound CCCCCCCCOB(OCCCCCCCC)OCCCCCCCC DTBRTYHFHGNZFX-UHFFFAOYSA-N 0.000 description 1
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- ZAGXLQIHXTXRFW-UHFFFAOYSA-N tris(2-ethyl-4-methylhexyl)-tris(2-ethyl-4-methylhexyl)silyloxysilane Chemical compound CCC(C)CC(CC)C[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)O[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)CC(CC)CC(C)CC ZAGXLQIHXTXRFW-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 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
- 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
- C10M145/38—Polyoxyalkylenes esterified
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/20—Tetrahydrofuran
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
-
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- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
- C10M107/34—Polyoxyalkylenes
-
- 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
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
-
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- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- 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
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- 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
-
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- 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
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- 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
- C10M2209/1065—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only 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
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- C10M2209/10—Macromolecular compoundss 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
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- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
- C10M2209/1095—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/011—Cloud point
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- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
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- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/071—Branched chain compounds
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- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/62—Food grade properties
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- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/70—Soluble oils
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- 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
- C10N2040/02—Bearings
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- 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
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- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
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- 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
- C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
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- 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
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- 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
- C10N2040/12—Gas-turbines
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- 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
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
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- 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
- C10N2040/20—Metal working
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- 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
- C10N2040/20—Metal working
- C10N2040/242—Hot working
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- 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
- C10N2040/20—Metal working
- C10N2040/243—Cold working
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- 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
- C10N2040/25—Internal-combustion engines
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- 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
- C10N2040/30—Refrigerators lubricants or compressors lubricants
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- 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
- C10N2040/32—Wires, ropes or cables lubricants
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- 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
- C10N2040/36—Release agents or mold release agents
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- 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
- C10N2040/46—Textile oils
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- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- the presently claimed invention is directed to the use of polyalkylene glycol ester that are prepared by reacting polytetrahydrofurane with at least one C9-C27 acid in lubricating oil composi- tions.
- Lubricating oil compositions are used in a variety of applications, such as industrial applications, transportation and engines.
- Industrial applications comprise of applications such as hydraulic oil, air compressor oil, gas compressor oil, gear oil, bearing and circulating system oil, refrigera- tor compressor oil and steam and gas turbine oils.
- Conventional lubricating oil compositions comprise base stocks, co-solvents and additives.
- the base stock is in each case selected according to the viscosity that is desired in the envisioned application. Combinations of base stocks of different viscosities, i.e. low and high viscos- ity respectively, are often used to adjust the needed final viscosity.
- the co-solvents are used to dissolve polar additives in usually less polar or unpolar base stocks.
- antioxidants are antioxidants, detergents, anti-wear additives, metal deactivator, corrosion inhibitors, friction modifiers, extreme-pressure additives, defoamers, anti-foaming agents, viscosity index improvers and demulsifying agents. These additives are used to impart further advantageous properties to the lubricating oil composition including longer stability and additional protection.
- lubricating oil compositions have to be replaced for var- ious reasons such as lubricity loss and/or product degradation.
- a certain residue of the lubricating oil composition (hold-up) remains in the machine, engine, gear etc. it is used in.
- the used and new lubricants are mixed with each other.
- compatibility between the old and new lubricant is very important.
- the efficiency can be increased if losses are minimized.
- the losses can be categorized in losses without and with load, their sum being the total losses.
- lubricant viscosity has a major effect on losses without load, i.e. spilling: Losses with load can be influenced by a low friction coefficient.
- energy efficiency strongly depends on the friction coefficient measured for a lubricant.
- the friction coefficient can be measured with several methods like Mini-Traction-Machine
- MTM cold rolling mill lubricants for steel sheets containing polyalkylene glycol esters that are prepared from polyethylene glycol and linear fatty acids.
- compositions comprising at least one base oil which is a polyether and a thickener.
- JP Patent Appl. Publ. No. 2005-232434 and JP Patent Appl. Publ. No. 2008-7741 describe a bearing lubricant comprising polyalkylene glycol ester derived from linear or branched saturated aliphatic monocarboxylic acid and polyalkylene glycol.
- US 5,744,432 discloses polyester which are the reaction product of one or more carboxylic acids and a polyalkylene glycol. These polyester are used in aqueous-based stamping lubricants.
- polyalkylene glycol ester that are prepared by reacting poly- tetrahydrofurane with at least one C9-C27 acid show a low friction coefficient and are compatible with base stocks that are conventionally used in lubricating oil compositions such as mineral oils and polyalphaolefins, preferably low viscosity polyalphaolefins, and consequently can be used for the formulation of lubricating oil compositions.
- the presently claimed invention is directed to the use of poly- alkylene glycol ester of general formula (I)
- k is an integer in the range of ⁇ 2 to ⁇ 30, and
- R 1 and R 2 identical or different, each denote an unsubstituted, branched alkyl
- lubricant in the sense of the presently claimed invention, is meant a substance capable of reducing friction between surfaces.
- branched denotes a chain of atoms with one or more side chains attached to it. Branching occurs by the replacement of a substituent, e.g., a hydrogen atom, with a covalent- ly bonded alkyl radical.
- Alkyl radical denotes a moiety constituted solely of atoms of carbon and of hydrogen without any kind of unsaturation, e.g. double bonds and/or triple bonds.
- a branched alkyl radical contains at least one branched carbon atom, more preferably 1 or 2 or 3 branched carbon atoms, even more preferably 1 or 2 branched carbon atoms, most preferably 1 branched carbon atom.
- branched carbon atom means a carbon atom in an alkyl radical (3° carbon atoms) which is bonded to three additional carbon atoms, and a carbon atom in an alkyl radical (4° carbon atoms) which is bonded to four additional carbon atoms.
- inventively claimed polyalkylene glycol esters of general formula (I) are oil soluble, which means that, when mixed with mineral oils and/or polyalphaolefins, preferably low viscosity poly- alphaolefins, in a weight ratio of 10:90, 50:50 and 90:10, the inventively claimed polyalkylene glycol esters of general formula (I) do not show phase separation after standing for 24 hours at room temperature for at least two weight rations out of the three weight ratios 10:90, 50:50 and 90:10.
- the polyalkylene glycol esters of general formula (I) have a kinematic viscosity in the range of ⁇ 30 mm 2 /s to ⁇ 300 mm 2 /s, more preferably in the range of ⁇ 30 mm 2 /s to ⁇ 280 mm 2 /s, at 40 °C, determined according to ASTM D 445.
- the polyalkylene glycol esters of general formula (I) have a kinematic viscosity in the range of ⁇ 5 mm 2 /s to ⁇ 60 mm 2 /s, more preferably in the range of ⁇ 7 mm 2 /s to ⁇ 55 mm 2 /s, at 100 °C, determined according to ASTM D 445.
- the polyalkylene glycol esters of general formula (I) have a pour point in the range of > - 40 °C to ⁇ 0 °C, more preferably in the range of > - 30 °C to ⁇ 0 °C, determined according to DIN ISO 3016.
- the polyalkylene glycol esters of general formula (I) have a weight average molecular weight Mw in the range of 500 to 4500 g/mol, more preferably in the range of 500 to 4000 g/mol, most preferably in the range of 600 to 3500 g/mol, even more preferably in the range of 700 to 3500 g/mol determined, determined according to DIN 55672-1 .
- the polyalkylene glycol esters of general formula (I) have a number average molecular weight Mn in the range of 400 to 4000 g/mol, more preferably in the range of 500 to 3500 g/mol, most preferably in the range of 500 to 3000 g/mol, even more preferably in the range of 500 to 2500 g/mol determined, determined according to DIN 55672-1.
- the polyalkylene glycol esters of general formula (I) have a polydispersity in the range of 1 .1 to 2.0, more preferably in the range of 1.1 to 1 .9, most preferably in the range of 1 .1 to 1.8, determined according to DIN 55672-1.
- the polyalkylene glycol esters of general formula (I) have a total acid number in the range of ⁇ 0.01 to ⁇ 2.5 mg KOH/g, more preferably in the range of ⁇ 0.01 to ⁇ 2.4 mg KOH/g, most preferably in the range of ⁇ 0.05 to ⁇ 2.2 mg KOH/g determined according to ASTM D664.
- the polyalkylene glycol esters of general formula (I) have a hydroxyl number in the range of ⁇ 0.1 to ⁇ 20 mg KOH/g, determined according to DIN 53240.
- k is an integer in the range of ⁇ 3 to ⁇ 25, more preferably k is an integer in the range of ⁇ 3 to ⁇ 20, most preferably in the range of ⁇ 5 to ⁇ 20, even more preferably in the range of > 6 to ⁇ 16.
- R 1 and R 2 each denote an unsubstituted, branched alkyl radical having 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22 carbon atoms. More preferably R 1 and R 2 , identical or different, each denote an unsubstituted, branched alkyl radical having 15, 16, 17, 18, 19 or 20 carbon atoms. Preferably R 1 and R 2 are identical and each denote an unsubstituted, branched alkyl radical having 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22 carbon atoms. More preferably R 1 and R 2 are identical and each denote an unsubstituted, branched alkyl radical having 15, 16, 17, 18, 19 or 20 carbon atoms.
- R 1 and R 2 identical or different, more preferably identical, each denote a moiety selected from the group consisting of
- n is an integer in the range of ⁇ 8 to ⁇ 23,
- m is an integer in the range of ⁇ 7 to ⁇ 22,
- o is an integer in the range of ⁇ 1 to ⁇ 6
- p is an integer in the range of ⁇ 2 to ⁇ 19
- (o+p) is an integer in the range of ⁇ 8 to ⁇ 21
- Q is an integer in the range of ⁇ 1 to ⁇ 6
- R is an integer in the range of ⁇ 2 to ⁇ 19
- (Q+R) is an integer in the range of ⁇ 8 to ⁇ 20.
- k is an integer in the range of ⁇ 3 to ⁇ 25,
- R 1 and R 2 identical, each denote a moiety selected from the group consisting of
- n is an integer in the range of ⁇ 10 to ⁇ 18,
- the presently claimed invention is directed to the use of an polyalkylene glycol esters of general formula (I)
- k is an integer in the range of ⁇ 3 to ⁇ 20,
- R 1 and R 2 identical, each denote a moiety selected from the group consisting of
- n is an integer in the range of ⁇ 1 1 to ⁇ 16,
- the polyalkylene glycol ester of general formula (I) are obtained by reacting at least one polytet- rahydrofurane block polymer with at least one C9-C27 acid, optionally in the presence of at least one catalyst.
- the polyalkylene glycol ester of general formula (I) are obtained by reacting at least one polytetrahydrofurane block polymer with at least one C9-C27 acid in the presence of at least one catalyst.
- the at least one C9-C27 acid is selected from the group consisting of 4,7-dimethyl- nonanoic acid, 4,8-dimethyl-decanoic acid, 8-methyl-undecanoic acid, iso-dodecanoic acid, 4,8-dimethyl-undecanoic acid, 4,9-dimethyl-undecanoic acid, iso-tridecanoic acid, 4,10- dimethyl-dodecanoic acid, iso-tetradecanoic acid, 4,1 1 -dimethyl-tridecanoic acid, iso- pentadecanoic acid, 8,10-dimethyl-tetradecanoic acid, 4,12-dimethyl-tetradecanoic acid, iso-hexadecanoic acid, 4,1 1 -dimethyl-pentadecanoic acid, 4,13-dimethyl-pentadecanoic acid, iso-heptadecanoic acid, anteiso heptade
- the at least one catalyst is a catalyst selected from the group consisting of magnesium carbonate, zinc carbonate, zinc borate, tin(ll) acetate , tin(ll) octanoate , tin(ll) lactate , zinc acetate, aluminum acetate, tin(li) trifluoromethane sulfonate, zinc trif!uoromethane sulfonate, magnesium trifluoromethane sulfonate, tin(ll) methane sulfonate, tin(ll) p-toluene sulfonate, dibutyltin dilaurate (DBTL), antimony oxide (Sb203), butyl titanate, isopropyl titanate, acetic acid, methane sulfonic acid, ethane sulfonic acid, 1 -propane sulfonic acid, 1 -butane sulfonic acid, trifluoride
- the presently claimed invention is directed to the use of at least one polyalkylene glycol esters of general formula (I) as defined above or a mixture of polyalkylene glycol esters of general formula (I) as defined above for the preparation of a lubricating oil composition.
- the presently claimed invention is directed to a lubricating oil composition
- a lubricating oil composition comprising at least one polyalkylene glycol esters of general formula (I) as defined above or a mixture of polyalkylene glycol esters of general formula (I) as defined above.
- the lubricating oil composition comprises ⁇ 1 % to ⁇ 10 % by weight or > 1 % to ⁇ 40 % by weight or > 20 % to ⁇ 100 % by weight,
- the lubricating oil composition according to the presently claimed invention has a friction coefficient in the range of 0.003 to 0.030, more preferably in the range of 0.003 to 0.020, at 25% slide roll ratio (SRR) determined using mini-traction machine (MTM) measurements at 70 °C and 1 GPa.
- SRR slide roll ratio
- MTM mini-traction machine
- the presently claimed invention relates to an industrial oil comprising at least one polyalkylene glycol esters of general formula (I) as defined above.
- Lubricating oil compositions comprising at least one polyalkylene glycol esters of general formula (I) as defined above or a mixture of polyalkylene glycol esters of general formula (I) as defined above can be used for various applications such as light, medium and heavy duty engine oils, industrial engine oils, marine engine oils, automotive engine oils, crankshaft oils, compres- sor oils, refrigerator oils, hydrocarbon compressor oils, very low-temperature lubricating oils and fats, high temperature lubricating oils and fats, wire rope lubricants, textile machine oils, refrigerator oils, aviation and aerospace lubricants, aviation turbine oils, transmission oils, gas turbine oils, spindle oils, spin oils, traction fluids, transmission oils, plastic transmission oils, passenger car transmission oils, truck transmission oils, industrial transmission oils, industrial gear oils, insulating oils, instrument oils, brake fluids, transmission liquids, shock absorber oils, heat distribution medium oils, transformer oils, fats, chain oils, minimum quantity lubricants for metal- working operations, oil to the warm and cold working, oil for water-
- a lubricating oil composition can comprise base stocks, co-solvents and a variety of different additives in varying ratios.
- the lubricating oil composition further comprises base stocks selected from the group consisting of mineral oils (Group I, II or III oils), polyalphaolefins (Group IV oils), polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters (Group V oils).
- base stocks selected from the group consisting of mineral oils (Group I, II or III oils), polyalphaolefins (Group IV oils), polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters (Group V oils).
- the lubricating oil comprises ⁇ 50 % to ⁇ 99 % by weight or > 80 % to ⁇ 99 % by weight or > 90 % to ⁇ 99 % by weight base stocks, related to the total amount of the lubricating oil composition.
- Group I base stocks contain less than 90 percent saturates and/or greater than 0.03 percent sulphur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in the following table
- Group II base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulphur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in the following table
- Group III base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulphur and have a viscosity index greater than or equal to 120 using the test methods specified in the following table
- Group IV base stocks contain polyalphaolefins.
- Synthetic lower viscosity fluids suitable for the present invention include the polyalphaolefins (PAOs) and the synthetic oils from the hy- drocracking or hydroisomerization of Fischer Tropsch high boiling fractions including waxes. These are both stocks comprised of saturates with low impurity levels consistent with their synthetic origin.
- the hydroisomerized Fischer Tropsch waxes are highly suitable base stocks, comprising saturated components of iso-paraffinic character (resulting from the isomerization of the predominantly n-paraffins of the Fischer Tropsch waxes) which give a good blend of high viscosity index and low pour point.
- Polyalphaolefins suitable for the present invention include known PAO materials which typically comprise relatively low molecular weight hydrogenated polymers or oligomers of alphaole- fins which include but are not limited to C2 to about C32 alphaolefins with the Cs to about C 16 alphaolefins, such as 1 -octene, 1 -decene, 1 -dodecene and the like being preferred.
- the preferred polyalphaolefins are poly-1 -octene, poly-1 -decene, and poly-1 -dodecene, although the dimers of higher olefins in the range of C14 to C18 provide low viscosity base stocks.
- Low viscosity PAO fluids suitable for the present invention may be conveniently made by the polymerization of an alphaolefin in the presence of a polymerization catalyst such as the Friedel-
- Crafts catalysts including, for example, aluminum trichloride, boron trifluoride or complexes of boron trifluoride with water, alcohols such as ethanol, propanol or butanol, carboxylic acids or esters such as ethyl acetate or ethyl propionate.
- alcohols such as ethanol, propanol or butanol
- carboxylic acids or esters such as ethyl acetate or ethyl propionate.
- Patents 4,149,178 or 3,382,291 may be conveniently used herein. Other descriptions of PAO synthesis are found in the following U.S. Patents: 3,742,082 (Brennan); 3,769,363 (Brennan);
- Group V base stocks contain any base stocks not described by Groups I to IV.
- Examples of Group V base stocks include alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters.
- Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(l -hexenes), poly(1 - octenes), poly(l -decenes)); alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenols); and alkylated diphenyl ethers and alkylated diphenyl sulphides and derivative, analogs and homologs thereof.
- carboxylic acid esters suitable for the present invention include the esters of mono and polybasic acids with monoalkanols (simple esters) or with mixtures of mono and polyalkanols (complex esters), and the polyol esters of monocarboxylic acids (simple esters), or mixtures of mono and polycarboxylic acids (complex esters).
- Esters of the mono/polybasic type include, for example, the esters of monocarboxylic acids such as heptanoic acid, and dicarboxylic acids such as phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malo- nic acid, alkenyl malonic acid, etc., with a variety of alcohols such as butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, or mixtures thereof with polyalkanols, etc.
- monocarboxylic acids such as heptanoic acid
- dicarboxylic acids such as phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azela
- esters include nonyl heptanoate, dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, dibutyl -TMP- adipate, etc.
- esters such as those obtained by reacting one or more polyhydric alcohols, preferably the hindered polyols such as the neopentyl polyols, e.g. neopentyl glycol, trimethylol ethane, 2-methyl-2-propyl-1 ,3-propanediol, trimethylol propane, trimethylol butane, pentaerythritol and dipentaerythritol with monocarboxylic acids containing at least 4 carbons, normally the Cs to C30 acids such as saturated straight chain fatty acids including caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, and behenic acid, or the corresponding branched chain fatty acids or unsaturated fatty acids such as oleic acid, or mixtures thereof, with polycarboxylic acids.
- the hindered polyols such as the neopentyl poly
- Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of known synthetic lubricating oils. These are exemplified by polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide, and the alkyl and aryl ethers of polyoxyalkylene polymers (e.g., methyl-polyiso-propylene glycol ether having a molecular weight of 1000 or diphenyl ether of poly-ethylene glycol having a molecular weight of 1000 to 1500); and mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C3-C8 fatty acid esters and C13 Oxo acid diester of tetraethylene glycol.
- polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide
- alkyl and aryl ethers of polyoxyalkylene polymers e.g.,
- Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy- or polyaryloxysilicone oils and silicate oils comprise another useful class of synthetic lubricants; such oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2- ethylhexyl)silicate, tetra-(4-methyl-2-ethylhexyl)silicate, tetra-(p-tert-butyl-phenyl) silicate, hexa-(4-methyl-2-ethylhexyl)disiloxane, oly(methyl)siloxanes and poly(methylphenyl)siloxanes.
- oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2- ethylhexyl)silicate, tetra-(4-methyl-2-ethy
- Other synthetic lubricating oils include liquid esters of phosphorous-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid) and polymeric tetrahydrofurans.
- the lubricating oil composition of the invention optionally further includes at least one other performance additive.
- the other performance additives include dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulphur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, demulsi- fiers, pour point depressants, seal swelling agents, friction modifiers and mixtures thereof.
- the total combined amount of the other performance additives (excluding the viscosity modifiers) present on an oil free basis may include ranges of 0 % by weight to 25 % by weight, or 0.01 % by weight to 20 % by weight, or 0.1 % by weight to 15 % by weight or 0.5 % by weight to 10 % by weight, or 1 to 5 % by weight of the composition.
- the other performance additives may be present, it is common for the other performance additives to be present in different amounts relative to each other.
- the lubricating composition further includes one or more viscosity modifiers.
- the viscosity modifier may be present in an amount of 0.5 % by weight to 70 % by weight, 1 % by weight to 60 % by weight, or 5 % by weight to 50 % by weight, or 10 % by weight to 50 % by weight of the lubricating composition.
- Viscosity modifiers include (a) polymethacrylates, (b) esterified copolymers of (II) a vinyl aromatic monomer and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) esterified interpolymers of (II) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) hydrogenated copolymers of styrene-butadiene, (e) ethylene- propylene copolymers, (f) polyisobutenes, (g) hydrogenated styrene-isoprene polymers, (h) hydrogenated isoprene polymers, or (II) mixtures thereof.
- the viscosity modifier includes (a) a polymethacrylate, (b) an esterified copolymer of (II) a vinyl aromatic monomer; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) an esterified interpolymer of (II) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) mixtures thereof.
- Extreme pressure agents include compounds containing boron and/or sulphur and/or phosphorus.
- the extreme pressure agent may be present in the lubricating composition at 0 % by weight to 20 % by weight, or 0.05 % by weight to 10 % by weight, or 0.1 % by weight to 8 % by weight of the lubricating composition.
- the extreme pressure agent is a sulphur- containing compound.
- the sulphur-containing compound may be a sulphurised olefin, a polysulphide, or mixtures thereof.
- the sulphurised olefin include a sulphurised olefin derived from propylene, isobutylene, pentene; an organic sulphide and/or polysulphide including benzyldi- sulphide; bis-(chlorobenzyl) disulphide; dibutyl tetrasulphide; di-tertiary butyl polysulphide; and sulphurised methyl ester of oleic acid, a sulphurised alkylphenol, a sulphurised dipentene, a sulphurised terpene, a sulphurised Diels-Alder adduct, an alkyl sulphenyl N'N- dialkyl
- the extreme pressure agent sulphur-containing compound includes a di- mercaptothiadiazole or derivative, or mixtures thereof.
- the dimercaptothiadiazole include compounds such as 2, 5-dimercapto-1 ,3,4-thiadiazole or a hydrocarbyl-substituted 2, 5-dimercapto-1 ,3,4-thiadiazole, or oligomers thereof.
- the oligomers of hydrocarbyl- substituted 2, 5-dimercapto-1 ,3,4-thiadiazole typically form by forming a sulphur-sulphur bond between 2, 5-dimercapto-1 ,3,4-thiadiazole units to form derivatives or oligomers of two or more of said thiadiazole units.
- Suitable 2, 5-dimercapto-1 ,3,4-thiadiazole derived compounds include for example 2, 5-bis(tert-nonyldithio)-1 ,3,4-thiadiazole or 2-tert-nonyldithio-5-mercapto-1 ,3,4- thiadiazole.
- the number of carbon atoms on the hydrocarbyl substituents of the hydrocarbyl- substituted 2,5-dimercapto-1 ,3,4-thiadiazole typically include 1 to 30, or 2 to 20, or 3 to 16.
- the dimercaptothiadiazole may be a thiadiazole-functionalised dispersant.
- a detailed description of the thiadiazole- functionalised dispersant is described is paragraphs [0028] to [0052] of International Publication WO 2008/014315.
- the thiadiazole-functionalised dispersant may be prepared by a method including heating, reacting or complexing a thiadiazole compound with a dispersant substrate.
- the thiadiazole com- pound may be covalently bonded, salted, complexed or otherwise solubilised with a dispersant, or mixtures thereof.
- the relative amounts of the dispersant substrate and the thiadiazole used to prepare the thiadiazole-functionalised dispersant may vary. In one embodiment the thiadiazole compound is present at 0.1 to 10 parts by weight relative to 100 parts by weight of the dispersant substrate. In different embodiments the thiadiazole compound is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or 0.2 to less than 5: to 100 parts by weight of the dispersant substrate.
- the relative amounts of the thiadiazole compound to the dispersant substrate may also be expressed as (0.1 -10):100, or (>0.1 -9):100, (such as (>0.5-9):100), or (0.1 to less than 5): 100, or (0.2 to less than 5): 100.
- the dispersant substrate is present at 0.1 to 10 parts by weight relative to 1 part by weight of the thiadiazole compound. In different embodiments the dispersant substrate is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or about 0.2 to less than 5: to 1 part by weight of the thiadiazole compound.
- the relative amounts of the dispersant substrate to the thiadiazole compound may also be expressed as (0.1 -10): 1 , or (>0.1 -9):1 , (such as (>0.5-9):1 ), or (0.1 to less than 5): 1 , or (0.2 to less than 5): 1.
- the thiadiazole-functionalised dispersant may be derived from a substrate that includes a suc- cinimide dispersant (for example, N-substituted long chain alkenyl succinimides, typically a pol- yisobutylene succinimide), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant, a polyetheramine dispersant, a viscosity modifier containing dispersant functionality (for example polymeric viscosity index modifiers (VMs) containing dispersant functionality), or mixtures thereof.
- the dispersant substrate includes a succinimide dispersant, an ester-containing dispersant or a Mannich dispersant.
- the extreme pressure agent includes a boron- containing compound.
- the boron-containing compound includes a borate ester (which in some embodiments may also be referred to as a borated epoxide), a borated alcohol, a borated dispersant, a borated phospholipid or mixtures thereof.
- the boron-containing compound may be a borate ester or a borated alcohol.
- the borate ester may be prepared by the reaction of a boron compound and at least one compound selected from epoxy compounds, halohydrin compounds, epihalohydrin compounds, alcohols and mixtures thereof.
- the alcohols include dihydric alcohols, trihydric alcohols or higher alcohols, with the proviso for one embodiment that hydroxyl groups are on adjacent carbon atoms, i.e., vicinal.
- Boron compounds suitable for preparing the borate ester include the various forms selected from the group consisting of boric acid (including metaboric acid, orthoboric acid and tetraboric acid), boric oxide, boron trioxide and alkyl borates.
- the borate ester may also be prepared from boron halides.
- suitable borate ester compounds include tripropyl borate, tributyl borate, tripentyl borate, trihexyl borate, triheptyl borate, trioctyl borate, trinonyl borate and tridecyl bo- rate.
- the borate ester compounds include tributyl borate, tri-2-ethylhexyl borate or mixtures thereof.
- the boron-containing compound is a borated dispersant, typically derived from an N-substituted long chain alkenyl succinimide.
- the borated dispersant includes a polyisobutylene succinimide. Borated dispersants are described in more detail in US Patents 3,087,936; and Patent 3,254,025.
- the borated dispersant may be used in combination with a sulphur- containing compound or a borate ester.
- the extreme pressure agent is other than a borated dispersant.
- the number average molecular weight of the hydrocarbon from which the long chain alkenyl group was derived includes ranges of 350 to 5000, or 500 to 3000, or 550 to 1500.
- the long chain alkenyl group may have a number average molecular weight of 550, or 750, or 950 to 1000.
- the N-substituted long chain alkenyl succinimides are borated using a variety of agents including boric acid (for example, metaboric acid, orthoboric acid and tetraboric acid), boric oxide, boron trioxide, and alkyl borates.
- boric acid for example, metaboric acid, orthoboric acid and tetraboric acid
- boric oxide for example, boron trioxide
- alkyl borates alkyl borates.
- the borating agent is boric acid which may be used alone or in combination with other borating agents.
- the borated dispersant may be prepared by blending the boron compound and the N- substituted long chain alkenyl succinimides and heating them at a suitable temperature, such as, 80 °C to 250 °C, or 90 °C to 230 °C, or 100 °C to 210 °C, until the desired reaction has occurred.
- the molar ratio of the boron compounds to the N-substituted long chain alkenyl succin- imides may have ranges including 10:1 to 1 :4, or 4:1 to 1 :3; or the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may be 1 :2.
- the ratio of moles B : moles N (that is, atoms of B : atoms of N) in the borated dispersant may be 0.25:1 to 10:1 or 0.33:1 to 4:1 or 0.2:1 to 1 .5:1 , or 0.25:1 to 1 .3:1 or 0.8:1 to 1 .2:1 or about 0.5:1
- An inert liquid may be used in performing the reaction.
- the liquid may include toluene, xylene, chlorobenzene, dimethylformamide or mixtures thereof.
- the lubricating composition further includes a borated phospholipid.
- the borated phospholipid may be derived from boronation of a phospholipid (for example borona- tion may be carried out with boric acid).
- Phospholipids and lecithins are described in detail in Encyclopedia of Chemical Technology, Kirk and Othmer, 3rd Edition, in “Fats and Fatty Oils", Volume 9, pages 795-831 and in "Lecithins", Volume 14, pages 250-269.
- the phospholipid may be any lipid containing a phosphoric acid, such as lecithin or cephalin, or derivatives thereof.
- phospholipids include phosphatidylcholine, phosphatidylser- ine, phosphatidylinositol, phosphatidylethanolamine, phosphotidic acid and mixtures thereof.
- the phospholipids may be glycerophospholipids, glycerol derivatives of the above list of phospholipids. Typically, the glycerophospholipids have one or two acyl, alkyl or alkenyl groups on a glycerol residue.
- the alkyl or alkenyl groups may contain 8 to 30, or 8 to 25, or 12 to 24 carbon atoms.
- suitable alkyl or alkenyl groups include octyl, dodecyl, hexadecyl, octade- cyl, docosanyl, octenyl, dodecenyl, hexadecenyl and octadecenyl.
- Phospholipids may be prepared synthetically or derived from natural sources. Synthetic phos- pholipids may be prepared by methods known to those in the art. Naturally derived phospholipids are often extracted by procedures known to those in the art. Phospholipids may be derived from animal or vegetable sources. A useful phospholipid is derived from sunflower seeds. The phospholipid typically contains 35 % to 60 % phosphatidylcholine, 20 % to 35 % phosphatidyl- inositol, 1 % to 25 % phosphatidic acid, and 10 % to 25 % phosphatidylethanolamine, wherein the percentages are by weight based on the total phospholipids.
- the fatty acid content may be 20 % by weight to 30 % by weight palmitic acid, 2 % by weight to 10 % by weight stearic acid, 15 % by weight to 25 % by weight oleic acid, and 40 % by weight to 55 % by weight linoleic acid.
- Friction modifiers may include fatty amines, esters such as borated glycerol esters, fatty phosphites, fatty acid amides, fatty epoxides, borated fatty epoxides, alkoxylated fatty amines, borated alkoxylated fatty amines, metal salts of fatty acids, or fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines.
- the lubricating composition may contain phosphorus- or sulphur- containing antiwear agents other than compounds described as an extreme pressure agent of the amine salt of a phosphoric acid ester described above.
- the antiwear agent may include a non-ionic phosphorus compound (typically compounds having phosphorus atoms with an oxidation state of +3 or +5), a metal dialkyldithiophosphate (typically zinc dialkyldithiophosphat.es), a metal mono- or di- alkylphosphate (typically zinc phosphates), or mixtures thereof.
- a non-ionic phosphorus compound typically compounds having phosphorus atoms with an oxidation state of +3 or +5
- a metal dialkyldithiophosphate typically zinc dialkyldithiophosphat.es
- a metal mono- or di- alkylphosphate typically zinc phosphates
- the non-ionic phosphorus compound includes a phosphite ester, a phosphate ester, or mixtures thereof.
- the lubricating composition of the invention further includes a dispersant.
- the dispersant may be a succinimide dispersant (for example N-substituted long chain alkenyl succinimides), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant or a polyetheramine dispersant.
- succinimide dispersant for example N-substituted long chain alkenyl succinimides
- a Mannich dispersant for example N-substituted long chain alkenyl succinimides
- an ester-containing dispersant for example N-substitute
- the succinimide dispersant includes a polyisobutylene-substituted succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000, or 950 to 1600.
- the dispersant includes a borated dispersant.
- the borated dispersant includes a succinimide dispersant including a polyisobutylene succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000. Borated dispersants are described in more detail above within the extreme pressure agent description.
- Dispersant viscosity modifiers include functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or es- terified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
- functionalised polyolefins for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or es- terified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
- Corrosion inhibitors include 1 -amino-2-propanol, octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and/or a fatty acid such as oleic acid with a polyamine.
- Metal deactivators include derivatives of benzotriazoles (typically tolyltriazole), 1 ,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles or 2-alkyldithiobenzothiazoles. The metal deactivators may also be described as corrosion inhibitors.
- Foam inhibitors include copolymers of ethyl acrylate and 2-ethylhexyl acrylate and optionally vinyl acetate.
- Demulsifiers include trialkyl phosphates, and various polymers and copolymers of ethylene glycol, ethylene oxide, propylene oxide, or mixtures thereof.
- Pour point depressants including esters of maleic anhydride-styrene, polymethacrylates, poly- acrylates or polyacrylamides.
- Seal swell agents including Exxon Necton-37TM (FN 1380) and Exxon Mineral Seal OilTM (FN 3200).
- the lubricating oil composition contains co-solvents selected from the group consisting of di-isodecyl adipate, di-propyladipate, di-isotridecyl adipate, trimethylpropyl tricaprylate, di- isooctyl adipate, di-ethylhexyl adipate and d-inonyl adipate.
- the lubricating oil composition contains co-solvents in an amount of ⁇ 0.5 % to ⁇ 35 % by weight, more preferably ⁇ 1 % to ⁇ 30 % by weight, related to the overall weight of the lubricating oil composition.
- the presently claimed invention is directed to a method for reducing the friction coefficient of a lubricating oil composition in the lubrication of a mechanical device com- prising formulating said lubricating oil composition with at least one polyalkylene glycol esters of general formula (I) as defined above or a mixture of polyalkylene glycol esters of general formula (I) as defined above.
- the friction-modification properties are determined by measuring the friction coefficient at 0 - 25% slide roll ratio (SRR), mean speed of 4m/s, using mini-traction machine (MTM) measurements at 70 °C and 1 GPa loading.
- Reducing the friction coefficient means in the sense of the presently claimed invention that the friction coefficient of a lubricating oil composition comprising a carboxylic acid ester as defined above is lower than the friction coefficient of a lubricating oil composition that does not contain said carboxylic acid ester.
- the presently claimed invention is directed to a method of enhancing the friction modification properties of a lubricating oil composition in the lubrication of a mechanical device comprising formulating said lubricating oil composition with at least one polyalkylene glycol esters of general formula (I) as defined above.
- Enhancing the friction-modification properties means in the sense of the present invention that the friction coefficient of a lubricating oil composition comprising a carboxylic acid ester as defined above is lower that the friction coefficient of a lubricating oil composition that does not con- tain said carboxylic acid ester.
- the friction-modification properties are determined by measuring the friction coefficient at 25% slide roll ratio (SRR) using mini-traction machine (MTM) measurements at 70 °C and 1 GPa.
- a mechanical device in the sense of the presently claimed invention is a mechanism consisting of a device that works on mechanical principles.
- the mechanical device is preferably selected from the group consisting of bearings, gears, joints and guidances.
- the mechanical device is operated at temperatures in the range of > - 80 °C to ⁇ 500 °C, most preferably in the range of > - 80 °C to ⁇ 250 °C .
- Mn number average molecular weight, determined according to DIN 55672-1 and referred to Polystyrene calibration standard.
- Mw weight average molecular weight, determined according to DIN 55672-1 and referred to Polystyrene calibration standard.
- SZ acid number, determined according to ASTM D664.
- kinematic viscosity was measured according to the standard international method ASTM D 445.
- the viscosity index was measured according to the ASTM D 2270.
- the pour point according was measured to DIN ISO 3016.
- Friction coefficient evaluation The fluids were tested in the MTM (Mini-Traction Machine) instrument using the so-called traction test mode. In this mode, the friction coefficient is measured at a constant mean speed over a range of slide roll ratios (SRR) to give the traction curve.
- the disc and ball used for the experiments were made of steel (AISI 52100), with a hardness of 750 HV and Ra ⁇ 0,02 ⁇ .
- the diameter was 45,0 mm and 19,0 mm for the disc and the ball respectively.
- the tractions curves were run with 1 ,00 GPa contact pressure, 4 m/s mean speed and 70°C temperature.
- the slide-roll ratio (SRR) was varied from 0 to 25% and the friction coefficient measured. Oil compatibility evaluation
- Polytetrahydrofurane (pTHF 250; MW 250.0 g/mol, 187 g, 0.75 mol) was mixed with isostearic acid (302.7 g/mol; 454.1 g, 1 .5 mol) and heated to 180 °C under nitrogen flow for 15 h until an acid number of 5,1 mg KOH/g is reached. Thereby 25 ml condensate water is obtained. Then tin (1 18 g/mol; 3.13 g, granules) is added. The reaction mixture is heated again to 180 °C and held at this temperature for 48 h. The acid number of the crude product had an acid number of 0.7 mg KOH/g.
- the reaction mixture was allowed to cool to 25 °C and 2,0 ml water and powdered sodium hydrogen carbonate (50 g) was added. The mixture was stirred for 12 h and press filtered (Filter Type Seitz K900). The final product was characterized:
- GPC Mn: 1 121 ; Mw: 1 168; D: 1 .04
- Polytetrahydrofurane (pTHF 650; MW 650.0 g/mol, 905 g, 1 .39 mol) was mixed with isostearic acid (302.7 g/mol; 843.2 g, 2.78 mol) and heated to 220 °C under nitrogen flow for 15 h until an acid number of 8,9 mg KOH/g. Thereby 50 ml condensate is obtained. Then tin octanoate (405 g/mol; 4.03 g, 10 mmol) is added. The reaction mixture is heated again to 220 °C and held at this temperature for 48 h. The acid number of the crude product had an acid number of 3.9 mg KOH/g.
- the reaction mixture was allowed to cool to 25 °C and 2.5 ml water and powdered sodium hydrogen carbonate (260 g) was added. The mixture was stirred for 12 h and press filtered (Filter Type Seitz K150). The final product was characterized:
- Polytetrahydrofurane (pTHF 1000; MW 1000 g/mol, 500 g, 1 .00 mol) was mixed with isostearic acid (302 g/mol; 302.7 g, 2.00 mol) and heated to 180 °C under nitrogen flow for 8 h until an acid number of 10.6 mg KOH/g. Thereby 14 ml condensate obtained. Then 0,5 g para-toluene sulfonic acid and tin powder (405 g/mol; 4.03 g, 5 mmol) is added. The reaction mixture is heat- ed to 180 °C and held at this temperature for 21 h. The acid number of the crude product had an acid number of 0.1 mg KOH/g. The reaction mixture was allowed to cool to 25 °C and powdered sodium hydrogen carbonate (50 g) was added. The mixture was stirred for 12 h and press filtered (Filter Type Seitz 900). The final product was characterized:
- Acid number SZ 0.1 mg KOH/ g, 99.9% turnover
- Polytetrahydrofurane (pTHF 650; MW 650.0 g/mol, 650 g, 1.00 mol) was mixed with 2- ethylhexanoic acid (144.2 g/mol; 288.4 g, 2.00 mol) and heated to 200 °C under nitrogen flow for 18 h until an acid number of 18.7 mg KOH/g. Thereby 17 ml condensate obtained. Then tin octanoate (405 g/mol; 4.03 g, 5 mmol) is added. The reaction mixture is heated to 240 °C and held at this temperature for 6 h. The acid number of the crude product had an acid number of 1 .1 mg KOH/g. The reaction mixture was allowed to cool to 25 °C and powdered sodium hydrogen carbonate (150 g) was added. The mixture was stirred for 12 h and press filtered (Filter Type Seitz K150). The final product was characterized:
- Polytetrahydrofurane (pTHF 650; MW 650.0 g/mol, 650 g, 0.50 mol) was mixed with stearic acid (284,5 g/mol; 284.5 g, 1 .0 mol) and heated to 220 °C under nitrogen flow for 92 h until an acid number of 4.08 mg KOH/g. Thereby 17 ml condensate obtained. Then tin octanoate (405 g/mol; 1 .82 g, 5 mmol) is added. The reaction mixture is heated to 220 °C and held at this temperature for 48 h. The acid number of the crude product had an acid number of 0.97 mg KOH/g.
- the reaction mixture was allowed to cool to 90 °C and 200 ml toluene was added to dissolve the product. Powdered sodium hydrogen carbonate (230 g) was added. The mixture was stirred for 12 h at 25 °C and press filtered (Filter Type Seitz K900). Toluene was removed from the filtrate at 60°C/10 mbar. The final product was characterized:
- Polybutylene oxide (MW 1242.0 g/mol, 621 g, 0.50 mol) was mixed with isostearic acid (284.4 g/mol; 285.7 g, 1 .0 mol) and heated to 220 °C under nitrogen flow for 20 h until an acid number of 7.2 mg KOH/g was reached. Thereby 30.2 ml condensate is obtained. Then tin octanoate (405 g/mol; 1 .2 g, 3 mmol) is added. The reaction mixture is heated again to 220 °C and held at this temperature for 8 h. The acid number of the crude product had a value of 0.1 mg KOH/g. The final product was characterized:
- the oil compatibility and friction data are summarized in Table 1 .
- the data demonstrate that the molecules derived from the present invention (Example 1 , 2 and 3), namely polyalkylene glycol esters produced by reacting polytetrahydrofuran (p-THF) with isostearic acid (ds) show compatibility with mineral oils and low viscosity polyalphaolefins whilst providing low friction coefficients ( ⁇ 0,015 at 25% SRR in MTM experiments).
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AU2016316437B2 (en) * | 2015-08-13 | 2018-10-04 | Fuchs Petrolub Se | Composition for minimum quantity lubrication, and use of same |
US9879198B2 (en) * | 2015-11-25 | 2018-01-30 | Santolubes Llc | Low shear strength lubricating fluids |
WO2019126924A1 (en) | 2017-12-25 | 2019-07-04 | Dow Global Technologies Llc | Modified oil soluble polyalkylene glycols |
JP7317188B2 (ja) | 2017-12-25 | 2023-07-28 | ダウ グローバル テクノロジーズ エルエルシー | 変性油溶性ポリアルキレングリコール |
CA3121705A1 (en) * | 2018-12-18 | 2020-06-25 | Basf Se | Gear oil composition |
CN113454192B (zh) * | 2019-03-05 | 2023-05-12 | 陶氏环球技术有限责任公司 | 聚亚烷基二醇润滑剂组合物 |
EP3935143B1 (de) * | 2019-03-05 | 2023-11-29 | Dow Global Technologies Llc | Verbesserte kohlenwasserstoffschmiermittelzusammensetzungen und verfahren zu ihrer herstellung |
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2014
- 2014-11-14 AU AU2014356756A patent/AU2014356756A1/en not_active Abandoned
- 2014-11-14 EP EP14798865.3A patent/EP3074489A1/de not_active Withdrawn
- 2014-11-14 JP JP2016534627A patent/JP2017501252A/ja not_active Withdrawn
- 2014-11-14 US US15/035,539 patent/US20160272916A1/en not_active Abandoned
- 2014-11-14 CN CN201480064285.3A patent/CN105765042A/zh active Pending
- 2014-11-14 CA CA2929468A patent/CA2929468A1/en not_active Abandoned
- 2014-11-14 KR KR1020167017011A patent/KR20160090872A/ko not_active Application Discontinuation
- 2014-11-14 WO PCT/EP2014/074595 patent/WO2015078707A1/en active Application Filing
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JP2002155171A (ja) * | 2000-09-07 | 2002-05-28 | Kao Corp | ゴム組成物 |
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JP2017501252A (ja) | 2017-01-12 |
AU2014356756A1 (en) | 2016-05-26 |
CN105765042A (zh) | 2016-07-13 |
WO2015078707A1 (en) | 2015-06-04 |
US20160272916A1 (en) | 2016-09-22 |
CA2929468A1 (en) | 2015-06-04 |
KR20160090872A (ko) | 2016-08-01 |
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