EP1853684A2 - Verfahren zur erhöhung der oxidationsstabilität industrieller flüssigkeiten - Google Patents
Verfahren zur erhöhung der oxidationsstabilität industrieller flüssigkeitenInfo
- Publication number
- EP1853684A2 EP1853684A2 EP06736719A EP06736719A EP1853684A2 EP 1853684 A2 EP1853684 A2 EP 1853684A2 EP 06736719 A EP06736719 A EP 06736719A EP 06736719 A EP06736719 A EP 06736719A EP 1853684 A2 EP1853684 A2 EP 1853684A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- fluid
- industrial fluid
- antioxidant
- oil
- additives
- 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.)
- Granted
Links
- 239000012530 fluid Substances 0.000 title claims abstract description 81
- 238000000034 method Methods 0.000 title claims abstract description 12
- 230000001590 oxidative effect Effects 0.000 title description 20
- 150000002148 esters Chemical class 0.000 claims abstract description 51
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 41
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 31
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 22
- 239000008158 vegetable oil Substances 0.000 claims abstract description 22
- 239000002199 base oil Substances 0.000 claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims abstract description 8
- 239000003921 oil Substances 0.000 claims description 35
- 235000019198 oils Nutrition 0.000 claims description 34
- 239000000654 additive Substances 0.000 claims description 30
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000003599 detergent Substances 0.000 claims description 8
- 239000002270 dispersing agent Substances 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 125000005266 diarylamine group Chemical group 0.000 claims description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003607 modifier Substances 0.000 claims description 6
- 239000003784 tall oil Substances 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 5
- 239000005749 Copper compound Substances 0.000 claims description 4
- 150000001880 copper compounds Chemical class 0.000 claims description 4
- 150000004986 phenylenediamines Chemical class 0.000 claims description 4
- 238000012360 testing method Methods 0.000 description 34
- 125000002347 octyl 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])[H] 0.000 description 25
- -1 e.g. Chemical group 0.000 description 18
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- 235000012424 soybean oil Nutrition 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 8
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- 244000188595 Brassica sinapistrum Species 0.000 description 5
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- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 4
- 235000006008 Brassica napus var napus Nutrition 0.000 description 4
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 4
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 4
- TUSUWHFYKZZRIG-JQWMYKLHSA-N C([C@@H](NC(=O)[C@@H](C(C)C)NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@H](CC(C)C)C(N)=O)C1=CC=CC=C1 Chemical compound C([C@@H](NC(=O)[C@@H](C(C)C)NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@H](CC(C)C)C(N)=O)C1=CC=CC=C1 TUSUWHFYKZZRIG-JQWMYKLHSA-N 0.000 description 4
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
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- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 238000005555 metalworking Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 3
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 3
- 240000002791 Brassica napus Species 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- QQGBDFMKLXCNHD-UHFFFAOYSA-N 2,2-bis(decanoyloxymethyl)butyl decanoate Chemical compound CCCCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC QQGBDFMKLXCNHD-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 2
- 125000002704 decyl 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])* 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl 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 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000011630 iodine Substances 0.000 description 2
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- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 125000002960 margaryl 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])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000001421 myristyl 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])[H] 0.000 description 2
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- 125000000913 palmityl 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])[H] 0.000 description 2
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- 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 2
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- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000004177 carbon cycle Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
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- 125000004185 ester group Chemical group 0.000 description 1
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- 239000013020 final formulation Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
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- 239000012208 gear oil Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000000755 henicosyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000010722 industrial gear oil Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000002463 lignoceryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 description 1
- KEZPMZSDLBJCHH-UHFFFAOYSA-N n-(4-anilinophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 KEZPMZSDLBJCHH-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- CVVFFUKULYKOJR-UHFFFAOYSA-N n-phenyl-4-propan-2-yloxyaniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1 CVVFFUKULYKOJR-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 125000002460 pentacosyl 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])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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 238000003976 plant breeding Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000002469 tricosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 125000005314 unsaturated fatty acid group Chemical group 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Definitions
- the present invention relates to industrial fluids. More particularly, the present invention relates to improved hydraulic fluids that exhibit oxidative stability, ready biodegradability, low volatility, and a high viscosity index.
- 6,531 ,429 discloses compositions comprising thiophosphoric acid esters and dithio phosphoric acid esters or phosphoric acid lhioesters and oil additives from the group of the polyol partial esters, amines and epoxides, and also to the use of those lubricant compositions in improving the performance properties of lubricants, such as greases, metal-working fluids, gear fluids or hydraulic fluids.
- dithiophosphoric acid esters or phosphoric acid thioesters are present in the compositions preferably in a concentration of less than 400 ppm.
- U. S. Patent No. 6,583,302 discloses the modification of triglyceride oils having unsaturated fatty acid substituents to convert sites of unsaturation to C 2 to C 10 diesters.
- the resulting derivatives are said to be characterized by thermal and oxidative stability, have low temperature performance properties, are environmentally-friendly, and have utility as hydraulic fluids, lubricants, metal working fluids and other industrial fluids.
- the triglyceride oils are most easily prepared via epoxidized vegetable oils which are converted to the diesters in either a one- or two-step reaction. Flider, F.
- Adhvaryu, A. et at, Industrial Crops and Products ⁇ :247-254 (2002) demonstrated the improved performance of epoxidized soybean oil (ESBO) over soybean oil (SBO) and genetically modified high oleic soybean oil (HOSBO) in certain high temperature lubricant applications. They validated the thermal and deposit forming tendencies of these oils using micro-oxidation and differential scanning calorimetry in conjunction with identification of oxidized products by infrared spectroscopy and also discussed the function of phenolic antioxidants in these oils. Boundary lubrication properties under high load and low speed were determined and the variations explained based on the structural differences of these vegetable oils.
- ECO epoxidized canola oil
- ECO polyunsaturated oil
- a large amount of antioxidant is required to protect vegetable oil.
- a smaller amount of antioxidant is required to stabilize ECO as compared to conventional vegetable oils.
- the price of ECO is higher than conventional canola oil, it is far less than HEAR.
- the present invention is directed to using an epoxidized vegetable oil or synthetic ester to make an oxidatively stable biodegradable industrial fluid wherein said fluid is used in combination with at least one antioxidant.
- an industrial fluid is defined as any of a class of biodegradable oils used for automotive engine oils, two-stroke engine oils, aviation turbine oils, automotive gear oils, industrial gear oils, hydraulic fluids, compressor oils, metalworking fluid, textile oils, chain saw oils, and greases.
- the present invention is directed to a biodegradable industrial fluid comprising an epoxidized vegetable oil and at least one antioxidant.
- the present invention is directed to a hydraulic fluid comprising an epoxidized tall oil ester and at least one antioxidant.
- the present invention is directed to a method for improving the oxidation stability of industrial fluids comprising employing as the base oil of said industrial fluid an epoxidized synthetic ester, wherein said ester is used in combination with at least one antioxidant.
- the industrial fluid is a hydraulic fluid.
- the tall oil employed in the practice of the present invention can be esterified either before or after it is epoxidized.
- the alkyl moiety of the ester portion preferably comprises from one to about eighteen carbon atoms, e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, isomers of the foregoing, and the like.
- the alkyl moiety of the ester group comprises from four to eight carbon atoms. More preferably, the alkyl moiety is 2-ethylhexyl, i.e., an isomer of octyl.
- Esterification and epoxidation of the tall oil can be carried out by methods well- known to those skilled in the art.
- antioxidants examples include alkylated diphenylamines and N-alkylated phenylenediamines.
- Secondary diarylamines are well known antioxidants and there is no particular restriction on the type of secondary diarylamine that can be used in the practice of the present invention.
- the secondary diarylamine antioxidant is of the general formula R 1 ! -NH-R j2 , where R 1 , and
- R 12 each independently represent a substituted or unsubstituted aryl group having 6 to 46 carbon atoms.
- substituents for the aryl group are aliphatic hydrocarbon groups such as alkyl having 1 to 40 carbon atoms, hydroxyl, carboxyl, amino, N-alkylated amino, N',N-dialkylated amino, nitro, or cyano.
- the aryl is preferably substituted or unsubstituted phenyl or naphthyl, particularly where one or both of the aryl groups are substituted with alkyl, such as one having 4 to 24 carbon atoms.
- Preferred alkylated diphenylamines that can be employed in the practice of the present invention include nonylated diphenylamine, octylated diphenylamine (e.g., di(octylphenyl)amine), styrenated diphenylamine, octylated styrenated diphenylamine, and butylated octylated diphenylamine.
- the alkyl moiety of 1 to 40 carbon atoms can have either a straight or a branched chain, which can be either a fully saturated or a partially unsaturated hydrocarbon chain, e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, 2-ethyl hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, oleyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, tricontyl, pentatriacontyl, tetracontyl, and the like, and isomers and
- Examples of some secondary diarylamines that can be employed in the practice of the present invention include: diphenylamine, dialkylated diphenylamine, trialkylated diphenylamine, or mixtures thereof, 3-hydroxydiphenylaniine, 4-hydroxydiphenylamine, N- phenyl- 1 ,2- ⁇ henylenediamine, N-phenyl- 1 ,4-phenylenediamine, mono- and/or di- butyldiphenylamine, mono- and/or di-octyldiphenylamine, mono- and/or di- nonyldiphenylamine, phenyl- ⁇ -naphthylamine, phenyl- ⁇ -naphthylainine, di- heptyldiphenylamine, mono- and/or di-( ⁇ -methylstyryl)diphenylamine, mono- and/or di- styryldiphenylamine, N,N'-diisopiOp
- antioxidant types that can be used in the practice of the present invention is the hindered phenolic type.
- oil soluble phenolic compounds may be listed alkylated monophenols, alkylated hydroquinones, hydroxylated thiodiphenyl ethers, alkylidenebis phenols, benzyl compounds, acylaminophenols, and esters and amides of hindered phenol-substituted alkanoic acids.
- 3,5-di- ⁇ butyl-4-hydroxy-hydrocinnamic acid, a C 7 -C 9 branched alkylester of 2,6-di- ⁇ -butyl-p-cresol, and mixtures thereof are included in the hydraulic fluid compositions.
- antioxidant type that can be used in combination with the additives of the present invention are oil soluble copper compounds, and the like.
- the base oil and antioxidants of the hydraulic fluids of this invention can be used in combination with other additives typically found in hydraulic and other industrial fluids, and such combinations may, in fact, provide synergistic effects toward improving the desired properties, such as improved deposit control, anti-wear, f ⁇ ctional, antioxidant, low temperature, and like properties, of the fluid.
- Typical additives found in hydraulic fluids include dispersants, detergents, rust inhibitors, antiwear agents, antifoamants, friction modifiers, seal swell agents, demulsifiers, VI improvers, and pour point depressants.
- dispersants examples include polyisobutylene succinimides, polyisobutylene succinate esters, Mannich Base ashless dispersants, and the like.
- detergents include metallic alkyl phenates, sulfurized metallic alkyl phenates, metallic alkyl sulfonates, metallic alkyl salicylates, and the like.
- anti-wear additives include organo borates, organo phosphites, organic sulfur-containing compounds, zinc dialkyl dithiophosphates, zinc diaryl dithiophosphates, phosphosulfurized hydrocarbons, and the like.
- friction modifiers include fatty acid esters and amides, organo molybdenum compounds, molybdenum dialkylthiocarbamates, molybdenum dialkyl ditbiophosphates, and the like.
- An example of an antifoamant is polysiloxane, and the like.
- An example of a rust inhibitor is polyoxyalkylene polyols, and the like.
- Examples of VI improvers include olefin copolymers and dispersant olefin copolymers, and the like.
- An example of a pour point depressant is polymethacrylate, and the like.
- compositions when containing these additives, typically are blended into the base oil in amounts that are effective to provide their normal attendant function.
- Effective amounts of such additives are illustrated as follows:
- Anti-Foaming Agents 0.001-0.1 0.001-0.01
- Antiwear Agents 0.001-5 0.001-1.5
- additive concentrates comprising concentrated solutions or dispersions of the subject additives whereby several additives can be added simultaneoiisly to the base oil to form the hydraulic fluid composition. Dissolution of the additive concentrate into the tall oil may be facilitated by solvents and by mixing accompanied with mild heating, but this is not essential.
- the concentrate or additive-package will typically be formulated to contain the additives in proper amounts to provide the desired concentration in the final formulation when the additive-package is combined with a predetermined amount of base lubricant.
- the additives can be added to small amounts of base oil or other compatible solvents to form additive-packages containing active ingredients in collective amounts of typically from about 2.5 to about 90%, and preferably from about 15 to about 75%, and most preferably from about 25 to about 60% by weight additives in the appropriate proportions with the remainder being base oil.
- the final formulations may employ typically about 1-20 wt. % of the additive-package with the remainder being base oil.
- weight percents expressed herein are based on active ingredient (AI) content of the additive, and/or upon the total weight of any additive- package or formulation, which will be the sum of the (AI) weight of each additive plus the weight of total oil or diluent.
- the preferred hydraulic fluid compositions of the invention contain the additives in a concentration ranging from about 0.01 to about 30 weight percent.
- a concentration range for the additives ranging from about 0.01 to about 10 weight percent based on the total weight of the composition is preferred.
- a more preferred concentration range is from about 0.2 to about 5 weight percent.
- fatty acid distributions of the vegetable oils employed herein are given in Table 1.
- Descriptions of the epoxidized vegetables and their iodine values (degree of unsaturation) are listed in Table 2.
- the detergents used were 400 TBN amorphous overbased calcium sulfonate (Calcinate C400CLR), 300 TBN amorphous overbased calcium sulfonate (Calcinate C300R), 400 TBN crystalline overbased calcium sulfonate (Calcinate C400W), and overbased calcium carboxylate (OBC)
- the antioxidants used were nonylated diphenyl amine (Naugalube 438L), 3,5-di-t-butyl-4-hydroxy- hydrocinnamic acid C 7 -C 9 branched alkyl ester (Naugalube 531), alkylated phenyl-alpha- naphthylamine (Naugalube APAN) and a tolutriazole derivative (Metal Passivator
- C16-0 is palmitic acid.
- Cl 8-0 is stearic acid.
- C 18-1 is oleic acid.
- C 18-2 is linoleic acid.
- Cl 8-3 is linolenic acid.
- C22-1 is erucic acid.
- Examples 1-3 demonstrate the poor oxidative stability of the typical vegetable oils (high erucic acid rapeseed oil, canola oil, and high oleic acid canola oil) in PDSC 5 RPVOT, and TOST testing Examples 4-6
- Examples 4-6 demonstrate the excellent oxidative stability of the typical epoxidized vegetable oils (canola oil, soybean oil, and linseed oil) in PDSC, RPVOT, and TOST testing.
- Example 7 demonstrates the synthetic ester OTE, based on octyl tallate, is significantly less oxidatively stable in PDSC, RPVOT, and TOST testing than its epoxidized octyl tallate ester analog in Example 9.
- Example 8 demonstrates another synthetic ester, based on trimethylol propane caprate, is significantly less oxidatively stable in PDSC, RPVOT, and TOST testing than the epoxidized octyl tallate ester in Example 9.
- Example 9 demonstrates the octyl tallate ester is stable in typical industrial lubricant testing (emulsion characteristics, four-bail wear, foaming tendency, PDSC 3 RPVOT, and " TOST).
- a comparative table of the stability of various baseline vegetable oil, epoxidized vegetable oils, esters and epoxidized esters was made in the presence of antioxidant in Table 4 (Examples 10- 19) 0230-PA
- Strip 1b 1b 1a 1b 1b 1b 2a 1b 2c lnsolubles % 0 0 0...000666 0 0 0 0 0 0...000555 0 0 0...000111 0 0 0...000777 0 0...000666 0 0 0...000777 0 0...000111 0 0 0...111444 - - -
- Examples 10-11 demonstrate the baseline oxidative stability of canola oil (COl) using aniinic antioxidant.
- Examples 12-13 demonstrate the baseline oxidative stability of high oleic acid canola oil (CO2) using aminic antioxidant.
- Examples 14-15 demonstrate the improved oxidative stability and demulsibility of epoxidized soybean oil (ESO) using aminic antioxidant. Examples 16-17
- Examples 16-17 demonstrate the improved oxidative stability of epoxidized octyl tallate ester (EOTE) using aminic antioxidant.
- EOTE epoxidized octyl tallate ester
- Examples 18-19 demonstrate the improved oxidative stability of epoxidized canola oil (ECO) using aminic antioxidant.
- ECO epoxidized canola oil
- Naugalube 438L 1.0 0.50 0.50 0.50 0.50 0.50 0.50 1.00
- Example 20 demonstrates the baseline performance of ethoxylated octyl tallate ester (EOTE) in industrial fluid testing.
- EOTE ethoxylated octyl tallate ester
- Examples 21-24 demonstrate the performance of ethoxylated octyl tallate ester
- Examples 25-26 demonstrate the poor oxidation performance of octyl tallate ester (OTE) compared to the epoxidized analogs (Example 20), but improved PDSC, hydrolytic stability, and RPVOT with the addition of antioxidant.
- OTE octyl tallate ester
- Examples 27-28 demonstrate the performance of ethoxylated octyl tallate ester (EOTE) with metal passivator in typical industrial fluid tests.
- EOTE ethoxylated octyl tallate ester
- the PDSC and RPVOT are all synergistically improved with the addition of the metal passivator.
- Examples 29-30 demonstrate the performance of ethoxylated octyl tallate ester (EOTE) with overbased sulfonate and ZDDP for EP/AW in typical industrial fluid tests.
- EOTE ethoxylated octyl tallate ester
- ZDDP ZDDP
- PDSC and RPVOT oxidative stability tests
- Examples 31-32 demonstrate the performance of octyl tallate ester (OTE) and ethoxylated octyl tallate ester (EOTE) with ZDDP for EP/AW in typical industrial fluid tests.
- OFTE octyl tallate ester
- EOTE ethoxylated octyl tallate ester
- the four-ball wear, PDSC, and RPVOT are all synergistically improved with the addition of the ZDDP.
- Naugalube 438L 0.50 0.50 0.25 0.25 0.25 0.50 0.25 0.25
- Examples 33-36 demonstrate the performance of ethoxylated octyl tallate ester (EOTE) with various overbased detergents and ZDDP for EP/AW in typical hydraulic fluid tests.
- EOTE ethoxylated octyl tallate ester
- Examples 37-38 demonstrate the performance of ethoxylated octyl tallate ester (EOTE) with overbased sulfonate and ZDDP for EP/AW in typical hydraulic fluid tests in optimized concentrations.
- EOTE ethoxylated octyl tallate ester
- ZDDP ZDDP
- Example 39 demonstrates the performance of ethoxylated octyl tallate ester (EOTE) with overbased sulfonate and ZDDP for EP/AW and GMO for lubricity in typical hydraulic fluid tests in optimized concentrations.
- EOTE ethoxylated octyl tallate ester
- ZDDP ethoxylated octyl tallate ester
- the emulsion, four-ball wear, hydrolytic stability, PDSC, and RPVOT performance was acceptable for a hydraulic fluid.
- Example 40 demonstrates the performance of ethoxylated octyl tallate ester (EOTE) with overbased sulfonate and sulfurized olefin for EP/AW in typical hydraulic fluid tests in optimized concentrations.
- EOTE ethoxylated octyl tallate ester
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- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65739505P | 2005-03-02 | 2005-03-02 | |
| PCT/US2006/007447 WO2006094138A2 (en) | 2005-03-02 | 2006-03-01 | Method for improving the oxidative stability of industrial fluids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1853684A2 true EP1853684A2 (de) | 2007-11-14 |
| EP1853684B1 EP1853684B1 (de) | 2012-11-14 |
Family
ID=38573225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP06736719A Expired - Lifetime EP1853684B1 (de) | 2005-03-02 | 2006-03-01 | Zusammensetzung und verfahren zur erhöhung der oxidationsstabilität industrieller flüssigkeiten |
Country Status (1)
| Country | Link |
|---|---|
| EP (1) | EP1853684B1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12168726B2 (en) | 2018-11-30 | 2024-12-17 | Si Group, Inc. | Antioxidant compositions |
-
2006
- 2006-03-01 EP EP06736719A patent/EP1853684B1/de not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2006094138A2 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12168726B2 (en) | 2018-11-30 | 2024-12-17 | Si Group, Inc. | Antioxidant compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1853684B1 (de) | 2012-11-14 |
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