EP0586194A1 - Antioxidanten für hoch einfach-ungesättigte pflanzliche Öle - Google Patents

Antioxidanten für hoch einfach-ungesättigte pflanzliche Öle Download PDF

Info

Publication number: EP0586194A1
Authority: EP; European Patent Office
Prior art keywords: carbon atoms; hydrocarbyl; alkyl; formula; composition
Prior art date: 1992-09-02
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

Application number

EP93306775A

Other languages

English (en)

French (fr)

Other versions

EP0586194B1 (de

Inventor

Virginia Anne Carrick

Cerita Temel

Paul Carl Naegely

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

Lubrizol Corp

Original Assignee

Lubrizol Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-09-02

Filing date

1993-08-26

Publication date

1994-03-09

1993-08-26 Application filed by Lubrizol Corp filed Critical Lubrizol Corp

1994-03-09 Publication of EP0586194A1 publication Critical patent/EP0586194A1/de

1999-05-06 Application granted granted Critical

1999-05-06 Publication of EP0586194B1 publication Critical patent/EP0586194B1/de

2013-08-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003963 antioxidant agent Substances 0.000 title claims abstract description 13
235000015112 vegetable and seed oil Nutrition 0.000 title claims description 6
239000008158 vegetable oil Substances 0.000 title claims description 6
239000000203 mixture Substances 0.000 claims abstract description 59
-1 alkyl phenol Chemical compound 0.000 claims abstract description 27
239000003921 oil Substances 0.000 claims abstract description 26
239000006078 metal deactivator Substances 0.000 claims abstract description 14
230000003078 antioxidant effect Effects 0.000 claims abstract description 12
150000004982 aromatic amines Chemical class 0.000 claims abstract description 5
235000013311 vegetables Nutrition 0.000 claims abstract description 4
241001465754 Metazoa Species 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 91
125000001183 hydrocarbyl group Chemical group 0.000 claims description 65
125000000217 alkyl group Chemical group 0.000 claims description 54
229910052739 hydrogen Inorganic materials 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 34
229910052698 phosphorus Inorganic materials 0.000 claims description 31
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 24
235000019198 oils Nutrition 0.000 claims description 24
239000011574 phosphorus Substances 0.000 claims description 24
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 21
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 20
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 20
125000001931 aliphatic group Chemical group 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
239000011593 sulfur Substances 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
150000001408 amides Chemical class 0.000 claims description 11
235000006708 antioxidants Nutrition 0.000 claims description 11
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 9
125000001118 alkylidene group Chemical group 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
239000012964 benzotriazole Substances 0.000 claims description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 5
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 5
229930195733 hydrocarbon Natural products 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
239000005642 Oleic acid Substances 0.000 claims description 4
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
125000001400 nonyl 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])[H] 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
235000014113 dietary fatty acids Nutrition 0.000 claims description 3
239000000194 fatty acid Substances 0.000 claims description 3
229930195729 fatty acid Natural products 0.000 claims description 3
150000004665 fatty acids Chemical class 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims 1
235000021281 monounsaturated fatty acids Nutrition 0.000 claims 1
125000005480 straight-chain fatty acid group Chemical group 0.000 claims 1
239000012530 fluid Substances 0.000 abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
239000000047 product Substances 0.000 description 19
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 10
239000000314 lubricant Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
235000019486 Sunflower oil Nutrition 0.000 description 6
238000001816 cooling Methods 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
239000002600 sunflower oil Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 5
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 5
239000000787 lecithin Substances 0.000 description 5
229940067606 lecithin Drugs 0.000 description 5
235000010445 lecithin Nutrition 0.000 description 5
239000010687 lubricating oil Substances 0.000 description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
150000003626 triacylglycerols Chemical class 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
235000013305 food Nutrition 0.000 description 4
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 4
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
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 4
238000010992 reflux Methods 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
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 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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 3
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
125000003944 tolyl group Chemical group 0.000 description 3
CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
235000021314 Palmitic acid Nutrition 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
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 2
230000015572 biosynthetic process Effects 0.000 description 2
238000002485 combustion reaction Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 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
239000012208 gear oil Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
229940035429 isobutyl alcohol Drugs 0.000 description 2
239000010705 motor oil Substances 0.000 description 2
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
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
125000001399 1,2,3-triazolyl group Chemical class N1N=NC(=C1)* 0.000 description 1
JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
HXQHRUJXQJEGER-UHFFFAOYSA-N 1-methylbenzotriazole Chemical compound C1=CC=C2N(C)N=NC2=C1 HXQHRUJXQJEGER-UHFFFAOYSA-N 0.000 description 1
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
235000017060 Arachis glabrata Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000018262 Arachis monticola Nutrition 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
241000282461 Canis lupus Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
244000020518 Carthamus tinctorius Species 0.000 description 1
235000003255 Carthamus tinctorius Nutrition 0.000 description 1
241000208818 Helianthus Species 0.000 description 1
235000019484 Rapeseed oil Nutrition 0.000 description 1
235000019485 Safflower oil Nutrition 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005097 cold rolling Methods 0.000 description 1
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239000002285 corn oil Substances 0.000 description 1
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230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
239000000539 dimer Substances 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
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125000005313 fatty acid group Chemical group 0.000 description 1
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125000000524 functional group Chemical group 0.000 description 1
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239000011521 glass Substances 0.000 description 1
239000004519 grease Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
230000001050 lubricating effect Effects 0.000 description 1
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 1
239000000463 material Substances 0.000 description 1
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239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
238000000034 method Methods 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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150000002989 phenols Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
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238000006116 polymerization reaction Methods 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
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239000011347 resin Substances 0.000 description 1
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239000003813 safflower oil Substances 0.000 description 1
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238000012031 short term test Methods 0.000 description 1
239000010802 sludge Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229940083466 soybean lecithin Drugs 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000008117 stearic acid 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
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940005741 sunflower lecithin Drugs 0.000 description 1
125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 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
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
125000002948 undecyl 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])[H] 0.000 description 1

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Definitions

the present invention relates to an anti-oxidant composition for triglyceride oils that contain at least a 60 percent monounsaturated content.
Triglyceride oils containing this anti-oxidant composition have utility in hydraulic fluids, two-cycle (two-stroke) internal combustion engines, gear oils, passenger car motor oils and as a food machinery lubricant.
Oxidative stability is an important requirement for all lubricants regardless of their use. Auto-oxidative breakdown is strongly catalyzed by traces of metal ions (especially copper and iron) which become solubilized when the lubricant contacts a metal surface. Organic compounds, particularly those comprising relatively long hydrocarbon segments, and particularly those containing unsaturation, are subject to auto-oxidation when they are contacted with oxygen. This, in turn, results in the deterioration of the base material, often leading to increases in the total acidity, formation of gums, discoloration, loss of physical properties such as tensile strength for resins, or elasticity for elastomers, loss of potency, polymerization rancidity and/or odor.
US Patent 5,102,567 (Wolf, April 7, 1992) relates to a lubricating oil provided to lubricate parts such as bearings, gears and slide mechanism particularly in food processing equipment.
the food grade lubricating oil provides oxidation, thermal and hydrolytic stability; protects against rusting and corrosion; provides wear protection, prevents foaming; and resists the formation of sludge.
US Patent 4,115,288 (Schmitt, September 19, 1978) is directed to a lubricant composition that is comprised of a major amount of a lubricating oil or grease and as an antiwear agent, a minor amount of a substituted 1,2,3-triazole characterized by the formula: wherein R1 and R2 are individually selected from the group consisting of an alkyl group containing from 1 to 18 carbon atoms; an aryl group, such as phenyl; hydrogen; and and where at least one of R1 and R2 is other than hydrogen and where n is an integer from 5 to 15.
US Patent 4,746,448 (Kenmochi et al, May 24, 1988) provides a cold rolling oil for steels which comprises (A) 40 to 90 wt % of a monoester of an aliphatic carboxylic acid having 12 to 22 carbon atoms and an aliphatic alcohol having 1 to 12 carbon atoms, (B) 0.5 to 10 wt % of at least one of a dimer acid and a polymerized acid of a higher aliphatic unsaturated acid having 16 to 20 carbon atoms, (C) 2 to 40 wt % of a polyester having a molecular weight of 750 to 7500 and (D) 0.1 to 10 wt % of a polymer compound having nitrogen atoms in a molecule having a molecular weight of 1000 to 100,000.
This invention comprises an anti-oxidant composition comprising a major amount of
the invention comprises an anti-oxidant composition comprising a major amount of:
a triglyceride oil which is a natural or synthetic oil of the formula
aliphatic hydrocarbyl groups having at least 60 percent monounsaturated character and containing from about 8 to about 24 carbon atoms.
hydrocarbyl group denotes a radical having a carbon atom directly attached to the remainder of the molecule.
the aliphatic hydrocarbyl groups include the following:
Naturally occurring triglycerides are either vegetable oil triglycerides or animal oil triglycerides.
the synthetic triglycerides are those formed by the reaction of one mole of glycerol with three moles of a fatty acid or mixture of fatty acids.
Preferred are vegetable oil triglycerides.
the fatty acid moieties are such that the triglyceride has a monounsaturated character of at least 60 percent, preferably at least 70 percent and most preferably at least 80 percent.
a triglyceride comprised exclusively of an oleic acid moiety has an oleic acid content of 100% and consequently a monounsaturated content of 100%.
the triglyceride is made up of acid moieties that are 70% oleic acid, 10% stearic acid, 5% palmitic acid, 7% linoleic and 8% hexadecanoic acid, the monounsaturated content is 78%.
the monounsaturated character be derived from an oleyl radical, i.e., is the residue of oleic acid.
the preferred triglyceride oils are high oleic (at least 60 percent) acid triglyceride oils.
Typical high oleic vegetable oils employed within the instant invention are high oleic safflower oil, high oleic corn oil, high oleic rapeseed oil, high oleic sunflower oil, high oleic soybean oil, high oleic cottonseed oil and high oleic palm olein.
a preferred high oleic vegetable oil is high oleic sunflower oil obtained from Helianthus SP available from SVO Enterprises Eastlake, Ohio as Sunyl R high oleic sunflower oil.
Component (B) is at least one alkyl phenol of the formula wherein R4 is an alkyl group containing from 1 up to about 24 carbon atoms and a is an integer of from 1 up to 5.
R4 contains from 4 to 18 carbon atoms and most preferably from 4 to 12 carbon atoms.
R4 may be either straight chained or branched chained and branched chained is preferred.
the preferred value for a is an integer of from 1 to 4 and most preferred is from 1 to 3.
An especially preferred value for a is 2. When a is not 5, it is preferred that the position para to the OH group be open.
the (B) component is an alkyl phenol, however, mixtures of alkyl phenols may be employed.
the phenol is a butyl substituted phenol containing 2 or 3 t-butyl groups.
a 2 or 3 t-butyl groups.
the t-butyl groups occupy the 2,6-position, that is, the phenol is sterically hindered:
the t-butyl groups occupy the 2,4,6-position.
Component (C) is at least one aromatic amine of the formula wherein R5 is and R6 and R7 are independently a hydrogen or an alkyl group containing from 1 up to 24 carbon atoms. Preferably R5 is and R6 and R7 are alkyl groups containing from 4 up to about 20 carbon atoms. In a particularly advantageous embodiment, component (C) comprises an alkylated diphenylamine such as nonylateddiphenylamine of the formula
metal deactivator may be employed wherein the metal deactivator is selected from the group consisting of:
a useful metal deactivator is benzotriazole compound of the formula wherein R8 is hydrogen a straight or branched-chain alkyl group containing from 1 up to about 24 carbon atoms, preferably 1 to 12 carbon atoms and most preferably 1 carbon atom.
R8 is hydrogen a straight or branched-chain alkyl group containing from 1 up to about 24 carbon atoms, preferably 1 to 12 carbon atoms and most preferably 1 carbon atom.
R8 is hydrogen a straight or branched-chain alkyl group containing from 1 up to about 24 carbon atoms, preferably 1 to 12 carbon atoms and most preferably 1 carbon atom.
R is 1 carbon atom
the benzotriazole compound is tolyltriazole of the formula Tolyltriazole is available under the trade name Cobratec TT-100 from Sherwin-Williams Chemical.
Another metal deactivator are the phosphatides of the formula wherein R9 and R10 are aliphatic hydrocarbyl groups containing from 8 to about 24 carbon atoms and G is selected from the group consisting of hydrogen, Preferably G is such that the phosphatide is lecithin.
Particularly effective phosphatides are soybean lecithin, corn lecithin, peanut lecithin, sunflower lecithin, safflower lecithin and rapeseed lecithin.
a third useful metal deactivator are the carbamates of the formula wherein R11 is an alkyl group containing from 1 to about 24 carbon atoms, phenyl or alkyl phenyl wherein the alkyl group contains from 1 to about 18 carbon atoms.
R11 is an alkyl group containing from 1 to 6 carbon atoms.
the groups R12 and R13 are hydrogen or an alkyl group containing from 1 to about 6 carbon atoms, with the proviso that R12 and R13 are not both hydrogen.
a fourth useful metal deactivator is citric acid or derivatives of citric acid of the formula wherein R14, R15 and R16 are independently hydrogen or aliphatic hydrocarbyl groups containing from 1 to about 12 carbon atoms, with the proviso that at least one of R14, R15 and R16 is an aliphatic hydrocarbyl group and preferably contains from 1 to about 6 carbon atoms.
the fifth useful metal deactivator is a coupled phosphorus-containing amide that is a statisticalmixture of compounds having the following formula
R17 and R18 each independently is a hydrocarbyl, a hydrocarbyl-based thio or preferably a hydrocarbyl-based oxy group wherein the hydrocarbyl portion contains 6 to 22 carbon atoms.
the hydrocarbyl portion of R17 and R18 generally contains from 1 to about 34 carbon atoms.
R17 and R18 will contain 6 to 12 carbon atoms in order to provide for sufficient oil solubility.
the hydrocarbyl portion of R17 and R18 independently can be alkyl or aromatic.
both R17 and R18 can be the same type of hydrocarbyl group, that is both alkyl or both aromatic, often one such group can be alkyl and the remaining group can be aromatic.
Different coupled phosphorus-containing amide compounds which are made by reacting a mixture of two or more different reactants each containing an alkyl hydrocarbyl group as well as an aromatic hydrocarbyl (R17 and R18) group therein. The same or different compounds are coupled via different coupling groups R24 to form a statistical mixture of coupled compounds or are reacted with different compounds to provide different functional groups R24 thereon.
the hydrocarbyl group of R17 and R18 is preferably an alkyl containing from 6 to 22 (more preferably 8-12) carbon atoms.
examples of such groups include hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, octadecyl, behenyl, and the like, including all isomers thereof.
R17 or R18 hydrocarbyl be an aromatic, it can be phenyl or naphthyl. Often times it will have an alkyl substituent thereon.
the alkyl-substituted aromatic can have an alkyl substituent containing from zero, that is phenyl, to about 28 carbon atoms, and preferably from about 7 to about 12 carbon atoms.
the aromatic substituent can contain preferably from about 6 to about 12 carbon atoms in the alkyl group thereof, that is, the alkyl-substituted aromatic.
the aromatic preferably is phenyl while the alkyl can be the same as set forth hereinabove.
alkyl groups on the aromatic nucleus include methyl, ethyl, propyl, butyl, pentyl, heptyl, octyl, decyl, behenyl, and the like including isomers thereof.
mixed hydrocarbyl (R17 and R18) portions of substituents include tolyl and octyl, tolyl and hexyl, isobutylphenyl and amyl, phenyl and isooctyl, and the like.
Mixed hydrocarbyl (R17 and R18) substituents are also assured when cresylic acids are utilized to form the phosphorus portion of the coupled phosphorus-containing amide compound.
the sources, type and variety of cresylic acids are known to those skilled in the art.
the number of different molecular entities in the mixture is further increased by the different coupling groups, R24 as defined above for coupled phosphorus-containing amide when n' is 2 or 3.
the alkyl hydrocarbyl substituent (R17 or R18) contains 6 or more carbon atoms. However, when X1 or X2 is oxygen and especially when X2 is oxygen, the alkyl hydrocarbyl substituent (R17 or R18) is 6 to 12 carbon atoms.
R19, R20, R21 and R22 each independently can be hydrogen or a saturated hydrocarbyl having up to 22 carbon atoms.
the saturated hydrocarbyl group can be an alkyl having from 1 to 22 carbon atoms, a cycloalkyl having from 4 to 22 carbon atoms, or an aromatic, an aromatic-substituted alkyl or an alkyl-substituted aromatic having from 6 to about 34 carbon atoms.
R19, R20, R21 and R22 is hydrogen or methyl with hydrogen being highly preferred.
R19, R20, R21 and R22 alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, etc., as well as isomers thereof whereas examples of specific aromatic groups include phenyl, tolyl, naphthyl, heptylphenyl, nonylphenyl, dodecylphenyl, wax-substituted phenyl, and the like.
n can be zero or 1.
n is 1.
R23 is hydrogen or an alkyl having from 1 to 22 carbon atoms with hydrogen being highly preferred.
Examples os specific alkyl groups include methyl, ethyl, propyl, butyl, and so forth including the various isomers thereof.
a particularly preferred embodiment of (D) (5) includes a statistical mixture (i.e., coupled and uncoupled compounds each with different substituent groups providing a variety of different compounds) of different phosphorus containing amide compounds bonded to or couple by different R24 groups with the proviso that in general coupled phosphorus-containing amide the mixture includes some compounds wherein n' is 1 and R24 is -CH2OH and also where n' is 2, R24 is Any such statistical mixture is likely to include some coupled amide compounds of coupled phosphorus-containing amide wherein R24 is methylene. When R24 is methylene, R17 and R18 generally must contain more than 6 carbon atoms in order to maintain good oil solubility.
R24 is selected from the group consisting of H, -ROH, - ROR, -RSR and RN(R)2 and when n' is 2 or 3, R24 is selected from the group consisting of and when n' is 3, R24 is wherein R is independently hydrogen or an alkyl moiety, alkylene or alkylidene of 1 to 12 carbon atoms and R' is hydrogen or an alkyl or carboxy alkyl moiety, alkylene or alkylidene of containing 1 to 60 carbon atoms, R is preferably methylene and R' is preferably an alkyl moiety of 1 to 28 carbons.
R and R' are linking groups, they may be alkylene and/or alkylidene, i.e., the linkage may be vicinal and/or geminal.
Cooling is continued to about 30°C and a vacuum is applied (15 mm. Hg). Toluene solvent is removed while raising the temperature to 110°C. The residue is filtered through a filter aid and the filtrate is the desired product.
the product contains 6.90% P (6.75% theory) and 2.92% N (2.97% theory).
a reaction vessel is charged with 820 parts of toluene and 930 parts (2.32 equivalents) of a O,O-dialkyl phosphorodithioic acid prepared from a mixture of 20 mole percent isobutyl alcohol and 80 mole percent 2-ethylhexyl alcohol.
a nitrogen atmosphere are added 178.6 parts (1.16 equivalents) of methylenebisacrylamide.
the mixture exotherms to about 65°C and is heated at about 80-85° for 2 hours.
a vacuum (30 mm. Hg) is applied.
Toluene solvent is removed while raising the temperature to 115°C.
the residue is filtered through a filter aid and the filtrate is the desired product.
the product contains 7.30% P (7.28% theory).
the mixture is heated at reflux (91-127°C) for 2 hours while removing 131 parts of water.
the mixture is cooled to 80°C and 3.1 parts (0.038 equivalent) of 50% aqueous sodium hydroxide solution is added. Cooling is continued to 50°C and a vacuum (30 mm. Hg) is applied. Toluene solvent is removed while raising the temperature to 110°C. The residue is filtered through a filter aid and the filtrate is the desired product.
the product contains 7.09% P (7.42% theory).
Example (D) (5)-8 water is removed using a Dean Stark trap at reflux for 6 hours. After 234 parts of water is collected (temperature is 120°C), the mixture is cooled to 30°C. A vacuum is applied (30 mm. Hg) while raising temperature to 115°C. The mixture is filtered through a filter aid and the filtrate is the desired product. The product contains 6.71% phosphorus.
the last remaining metal deactivator is a methylacrylate derivative formed by the reaction of equal molar amounts of a phosphorus acid of the formula with methylacrylate wherein X1 and X2 are as defined above in (D) (5) and R25 and R26 are each independently a hydrocarbyl, a hydrocarbyl-based thio or preferably a hydrocarbyl-based oxy group wherein the hydrocarbyl portion contains from 1 to about 30 carbon atoms.
R25 and R26 are hydrocarbyl-based oxy groups wherein the hydrocarbyl group contains from 1 to 12 carbon atoms and X1 and X2 are sulfur. Since the reaction does not go to completion, the remaining acidity is neutralized with propylene oxide.
RBOT rotary bomb oxidation test
the RBOT test is a rapid means of estimating the oxidation stability of lubricating oils.
the oil sample, water and a copper catalyst coil are placed in a covered glass container, and placed in a bomb equipped with a pressure gauge.
the bomb is charged with oxygen to a pressure of 90 psi (620 Kpa) and placed in a constant temperature oil bath maintained at 150°C and rotated at 100 rpm.
the pressure in the bomb is monitored continuously. At first the pressure increases sharply, typically to about 190-200 psi, because of the increase in temperature.
the pressure remains relatively stable, until the oil breaks down.
the bomb "life" of the sample is the time in minutes from the start of the test to a 25 psi drop from the established plateau pressure.
the test uses a 3m length of 14 Awg of copper wire which has been cleaned. The longer the "life", the more stable the oil formulation (i.e., the more effective the anti-oxidant).
composition of the present invention comprising components (A) and (B) and optionally (D) or (A), (B) and (C) and optionally (D) have utility in hydraulic fluids, two-cycle (two-stroke) internal combustion engines, gear oils, passenger car motor oils and as a food machinery lubricant.
the composition of this invention comprises a major amount of (A) and a minor amount (B) and optionally (D) or a major amount of (A) and a minor amount of (B) and (C) and optionally (D).
a major amount is meant more than 50%.
a minor amount is less than 50%. Examples of minor amounts are 1%, 25% and 49%.
Component Generally Preferred Most Preferred (A) 75 - 99 85 - 99 95 - 99 (B) 0.1 - 10 0.3 - 8 0.5 - 5 (C) 0.1 - 10 0.3 - 8 0.5 - 5 (D) 0 - 2 0 - 0.5 0 - 0.25 It is understood that other components besides (A), (B), (C) and (D) may be present within this composition.
triglyceride oil, component (A) is identified with a number such as Sunyl R 80 High Oleic Sunflower oil, it means that the oleic acid residue of the triglyceride is 80 percent. In some instances, more than one triglyceride oil is utilized. For example, 80 parts of Sunyl R 90 is blended with normal sunflower oil that contains 20% oleic acid residue to give a sunflower oil blend containing 76% oleic acid residue.

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Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Emergency Medicine (AREA)
Lubricants (AREA)
Fats And Perfumes (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)

EP93306775A 1992-09-02 1993-08-26 Antioxidanten für hoch einfach-ungesättigte pflanzliche Öle Expired - Lifetime EP0586194B1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US93924992A	1992-09-02	1992-09-02
US939249		1997-09-29

Publications (2)

Publication Number	Publication Date
EP0586194A1 true EP0586194A1 (de)	1994-03-09
EP0586194B1 EP0586194B1 (de)	1999-05-06

Family

ID=25472820

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP93306775A Expired - Lifetime EP0586194B1 (de)	1992-09-02	1993-08-26	Antioxidanten für hoch einfach-ungesättigte pflanzliche Öle

Country Status (6)

Country	Link
EP (1)	EP0586194B1 (de)
JP (1)	JP3548591B2 (de)
AT (1)	ATE179747T1 (de)
AU (1)	AU662650B2 (de)
DE (1)	DE69324746T2 (de)
ES (1)	ES2133363T3 (de)

Cited By (6)

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EP0714974A1 (de) *	1994-12-02	1996-06-05	The Lubrizol Corporation	Umweltfreundliche Schmiermittel mit Nahrungsmittelqualität aus essbaren Triglyceriden, die zugelassene Additive enthalten
US5580482A (en) *	1995-01-13	1996-12-03	Ciba-Geigy Corporation	Stabilized lubricant compositions
EP0806470A2 (de) *	1996-05-08	1997-11-12	The Lubrizol Corporation	Auf biologisch abbaubarem pflanzlichem Öl basierendes Schmierfett
EP1122298A3 (de) *	2000-02-04	2002-05-02	Nippon Mitsubishi Oil Corporation	Hydraulische Ölzusammensetzung mit verbesserten biolologisch abbaubaren Eigenschaften
WO2007135358A1 (en) *	2006-05-22	2007-11-29	Niche Products Limited	Improvements in and relating to hydraulic fluids
WO2009013275A1 (en) *	2007-07-23	2009-01-29	Shell Internationale Research Maatschappij B.V.	Lubricating composition for use in diesel engines compatible with biofuel

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Publication number	Priority date	Publication date	Assignee	Title
JP4562844B2 (ja) *	2000-02-23	2010-10-13	浜松ホトニクス株式会社	光電陰極及び電子管
JP2006274058A (ja) *	2005-03-29	2006-10-12	Nippon Oil Corp	農業又は林業機械用潤滑油
US8071515B2 (en)	2006-10-17	2011-12-06	Idemitsu Kosan Co., Ltd.	Lubricating oil composition
JP4689583B2 (ja) *	2006-11-24	2011-05-25	出光興産株式会社	油圧作動油組成物

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- 1993-08-26 EP EP93306775A patent/EP0586194B1/de not_active Expired - Lifetime
- 1993-08-26 ES ES93306775T patent/ES2133363T3/es not_active Expired - Lifetime
- 1993-08-26 AT AT93306775T patent/ATE179747T1/de not_active IP Right Cessation
- 1993-08-26 DE DE69324746T patent/DE69324746T2/de not_active Expired - Lifetime
- 1993-08-30 AU AU44992/93A patent/AU662650B2/en not_active Ceased
- 1993-09-02 JP JP21891593A patent/JP3548591B2/ja not_active Expired - Fee Related

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EP0714974A1 (de) *	1994-12-02	1996-06-05	The Lubrizol Corporation	Umweltfreundliche Schmiermittel mit Nahrungsmittelqualität aus essbaren Triglyceriden, die zugelassene Additive enthalten
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EP0721979A3 (de) *	1995-01-13	1997-04-16	Ciba Geigy Ag	Stabilisierte Schmiermittelzusammensetzungen
EP0806470A2 (de) *	1996-05-08	1997-11-12	The Lubrizol Corporation	Auf biologisch abbaubarem pflanzlichem Öl basierendes Schmierfett
EP1122298A3 (de) *	2000-02-04	2002-05-02	Nippon Mitsubishi Oil Corporation	Hydraulische Ölzusammensetzung mit verbesserten biolologisch abbaubaren Eigenschaften
WO2007135358A1 (en) *	2006-05-22	2007-11-29	Niche Products Limited	Improvements in and relating to hydraulic fluids
GB2438402B (en) *	2006-05-22	2011-06-01	Niche Products Ltd	Improvements in and relating to hydraulic fluids
WO2009013275A1 (en) *	2007-07-23	2009-01-29	Shell Internationale Research Maatschappij B.V.	Lubricating composition for use in diesel engines compatible with biofuel
CN101796171B (zh) *	2007-07-23	2014-12-17	国际壳牌研究有限公司	与生物燃料相容的用于柴油发动机中的润滑组合物

Also Published As

Publication number	Publication date
DE69324746D1 (de)	1999-06-10
AU4499293A (en)	1994-03-10
ATE179747T1 (de)	1999-05-15
EP0586194B1 (de)	1999-05-06
AU662650B2 (en)	1995-09-07
JP3548591B2 (ja)	2004-07-28
DE69324746T2 (de)	1999-10-21
JPH06172780A (ja)	1994-06-21
ES2133363T3 (es)	1999-09-16

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DE69709683T2 (de)	2002-09-12	Öllösliches kupfer enthaltende biodegradable abbaubare schmiermittelzusammensetzung von triglyzeriden
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