EP2554646B1 - Biodegradable lubricating oil composition having flame retardancy - Google Patents
Biodegradable lubricating oil composition having flame retardancy Download PDFInfo
- Publication number
- EP2554646B1 EP2554646B1 EP11765579.5A EP11765579A EP2554646B1 EP 2554646 B1 EP2554646 B1 EP 2554646B1 EP 11765579 A EP11765579 A EP 11765579A EP 2554646 B1 EP2554646 B1 EP 2554646B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- lubricating oil
- polyol
- oil composition
- biodegradable lubricating
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 74
- 239000010687 lubricating oil Substances 0.000 title claims description 68
- 229920005862 polyol Polymers 0.000 claims description 62
- -1 polyol ester Chemical class 0.000 claims description 53
- 239000003921 oil Substances 0.000 claims description 41
- 235000019198 oils Nutrition 0.000 claims description 41
- 150000003077 polyols Chemical class 0.000 claims description 26
- 239000002199 base oil Substances 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 241000196324 Embryophyta Species 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- 239000010720 hydraulic oil Substances 0.000 claims description 16
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 16
- 229920000193 polymethacrylate Polymers 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 14
- 238000005886 esterification reaction Methods 0.000 claims description 13
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 10
- 230000032050 esterification Effects 0.000 claims description 10
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 9
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000005642 Oleic acid Substances 0.000 claims description 9
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 9
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 8
- KSTVMGTVOPUBDE-UHFFFAOYSA-N acetyl chloride;pyridine Chemical compound CC(Cl)=O.C1=CC=NC=C1 KSTVMGTVOPUBDE-UHFFFAOYSA-N 0.000 claims description 6
- 235000019486 Sunflower oil Nutrition 0.000 claims description 5
- 230000001747 exhibiting effect Effects 0.000 claims description 5
- 239000002600 sunflower oil Substances 0.000 claims description 5
- 238000010998 test method Methods 0.000 claims description 5
- 239000000828 canola oil Substances 0.000 claims description 4
- 235000019519 canola oil Nutrition 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003549 soybean oil Substances 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 4
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 3
- 235000005687 corn oil Nutrition 0.000 claims description 3
- 239000002285 corn oil Substances 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 12
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 12
- 239000000654 additive Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 231100000209 biodegradability test Toxicity 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 241000894007 species Species 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920006243 acrylic copolymer Polymers 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 238000006065 biodegradation reaction Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- SXJBHJCKWQIWHA-UHFFFAOYSA-N 2-ethyl-2,3,3-trimethylbutanoic acid Chemical compound CCC(C)(C(O)=O)C(C)(C)C SXJBHJCKWQIWHA-UHFFFAOYSA-N 0.000 description 2
- YVKVCTLHBOMQDA-GNOQXXQHSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;(z)-octadec-9-enoic acid Chemical compound CCC(CO)(CO)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O YVKVCTLHBOMQDA-GNOQXXQHSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- NVWRNKASWSJTQR-SVMKZPJVSA-N CCCCCCCC\C=C/CCCCCCCC(O)=O.CC(C)CCCCCCCCCCCCCCC(O)=O Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O.CC(C)CCCCCCCCCCCCCCC(O)=O NVWRNKASWSJTQR-SVMKZPJVSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 241000276569 Oryzias latipes Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 150000003939 benzylamines Chemical class 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000000415 inactivating effect Effects 0.000 description 2
- YYVJAABUJYRQJO-UHFFFAOYSA-N isomyristic acid Chemical compound CC(C)CCCCCCCCCCC(O)=O YYVJAABUJYRQJO-UHFFFAOYSA-N 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 231100000820 toxicity test Toxicity 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 description 1
- NPMHELYJLOUPIZ-UHFFFAOYSA-N 2,2,3,4-tetramethylpentanoic acid Chemical compound CC(C)C(C)C(C)(C)C(O)=O NPMHELYJLOUPIZ-UHFFFAOYSA-N 0.000 description 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
- IKNDGHRNXGEHTO-UHFFFAOYSA-N 2,2-dimethyloctanoic acid Chemical compound CCCCCCC(C)(C)C(O)=O IKNDGHRNXGEHTO-UHFFFAOYSA-N 0.000 description 1
- OWEMTCOXFULTNW-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanoic acid Chemical compound CC(C)C(C)(C(C)C)C(O)=O OWEMTCOXFULTNW-UHFFFAOYSA-N 0.000 description 1
- RCOUDAFEYSTMPB-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(3,5-ditert-butyl-4-hydroxy-1-methylcyclohexa-2,4-dien-1-yl)methyl]-4-methylcyclohexa-1,5-dien-1-ol Chemical compound C1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC1(C)CC1(C)C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C1 RCOUDAFEYSTMPB-UHFFFAOYSA-N 0.000 description 1
- YURQLUXJGMVKDT-UHFFFAOYSA-N 2-(hydroxymethyl)-2-octylpropane-1,3-diol Chemical compound CCCCCCCCC(CO)(CO)CO YURQLUXJGMVKDT-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- QFWGJUQOWNHFKT-UHFFFAOYSA-N 2-tert-butyl-2,5,5-trimethylhexanoic acid Chemical compound CC(C)(C)CCC(C)(C(O)=O)C(C)(C)C QFWGJUQOWNHFKT-UHFFFAOYSA-N 0.000 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000721047 Danaus plexippus Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QQVGEJLUEOSDBB-KTKRTIGZSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CO)(CO)CO QQVGEJLUEOSDBB-KTKRTIGZSA-N 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- ALKZAGKDWUSJED-UHFFFAOYSA-N dinuclear copper ion Chemical compound [Cu].[Cu] ALKZAGKDWUSJED-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
- C10M2207/2895—Partial esters containing free hydroxy groups 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/401—Fatty vegetable or animal oils 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- 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
-
- 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
- C10N2030/02—Pour-point; Viscosity index
-
- 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
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- 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
- C10N2030/64—Environmental friendly compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- Patent Documents 1 to 4 propose the following hydraulic oils: a self-extinguishing hydraulic oil containing a compound produced through condensation reaction between hexachlorophosphazene, and a perfluoroalkyl alcohol or the like (Patent Document 1); a flame-retardant hydraulic oil containing a polymer compound, the compound containing, as main components, a polyol and a polyol partial ester (Patent Document 2); a flame-retardant hydraulic oil produced by incorporating a high-molecular-weight polymer and a low-molecular-weight polymer into a base oil containing a fatty acid ester or a phosphoric acid ester (Patent Document 3); and a hydraulic fluid composition containing a polyalkylene glycol base fluid, and an alkylene-vinyl ester copolymer which serves as an anti-mist additive and can be dissolved in the base fluid
- antioxidants such as 2,6-di-t-butyl-4-methylphenol and 4,4'-methylenebis(2,6-di-t-butyl-4-methylphenol); amine antioxidants such as N-phenyl- ⁇ -naphthylamine, N-phenyl- ⁇ -naphthylamine, phenothiazine, and monooctyldiphenylamine; sulfur-containing antioxidants such as alkyl disulfide and benzothiazole; and zinc dialkyldithiophosphate.
- phenolic antioxidants such as 2,6-di-t-butyl-4-methylphenol and 4,4'-methylenebis(2,6-di-t-butyl-4-methylphenol)
- amine antioxidants such as N-phenyl- ⁇ -naphthylamine, N-phenyl- ⁇ -naphthylamine, phenothiazine, and monooctyldiphenylamine
- the dispersant employed may be an ashless dispersant and/or a metal-containing detergent.
- the ashless dispersant include succinimides, boron-containing succinimides, benzylamines, and boron-containing benzylamines.
- the metal-containing detergents include neutral, basic, and perbasic metal sulfonates, metal phenates, metal salicylates, and metal phosphonates.
- the metal forming such a metal sulfonate, metal phenate, metal salicylate, or metal phosphonate is preferably, for example, an alkaline earth metal such as Ca or Mg.
- oily agent examples include alcohols, fatty acids, and fatty acid esters.
- fatty acid esters include esters formed of a C6 to C22 aliphatic carboxylic acid and a C1 to C18 aliphatic alcohol.
- preferred alcohols include C8 to C18 monovalent aliphatic saturated and unsaturated alcohols.
- Flash point was determined by means of a Cleveland open cup (COC) tester according to JIS K 2274.
- the corrosiveness of a sample was evaluated through the test tube method according to JIS K 2513 "Petroleum Products - Corrosiveness to Copper - Copper Strip Test.” The test was carried out at 100°C for three hours. The sample copper strip was observed for tarnish with reference to "Copper Strip Corrosion Standards," and a classification number from 1a to 4c was assigned to indicate the degree of corrosiveness. A smaller number represents lower corrosiveness, and corrosiveness increases in alphabetical order.
- the biodegradable lubricating oil composition of the present invention exhibits excellent flame retardancy and biodegradability. Therefore, the lubricating oil composition is suitable for use as, for example, a hydraulic oil employed as a power transmission fluid in a hydraulic system of, for example, a hydraulic machine or apparatus for power transmission, power control, power buffering, etc.; or a door closer oil employed for a door closer.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010084472A JP5764298B2 (ja) | 2010-03-31 | 2010-03-31 | 難燃性能を有する生分解性潤滑油組成物 |
| PCT/JP2011/057904 WO2011125679A1 (ja) | 2010-03-31 | 2011-03-29 | 難燃性能を有する生分解性潤滑油組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP2554646A1 EP2554646A1 (en) | 2013-02-06 |
| EP2554646A4 EP2554646A4 (en) | 2013-11-06 |
| EP2554646B1 true EP2554646B1 (en) | 2019-06-12 |
Family
ID=44762625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP11765579.5A Active EP2554646B1 (en) | 2010-03-31 | 2011-03-29 | Biodegradable lubricating oil composition having flame retardancy |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20130017984A1 (zh) |
| EP (1) | EP2554646B1 (zh) |
| JP (1) | JP5764298B2 (zh) |
| CN (1) | CN102812114A (zh) |
| TW (1) | TWI510611B (zh) |
| WO (1) | WO2011125679A1 (zh) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5925003B2 (ja) * | 2012-03-23 | 2016-05-25 | 出光興産株式会社 | 潤滑油組成物およびこれを用いた機器 |
| CN105176640A (zh) * | 2015-08-28 | 2015-12-23 | 黄进堂 | 一种抗氧化环保液压油 |
| US20170152458A1 (en) * | 2015-11-30 | 2017-06-01 | Nch Corporation | Hydraulic Fluid and Lubricant Compositions Using Biodiesel |
| CN105567378B (zh) * | 2015-12-28 | 2018-05-18 | 大庆市加通石油化工有限公司 | 一种生物降解润滑油 |
| CN106635247A (zh) * | 2016-12-08 | 2017-05-10 | 青岛中科润美润滑材料技术有限公司 | 一种环境友好型液压油组合物 |
| CN106867631A (zh) * | 2016-12-21 | 2017-06-20 | 苏州安美润滑科技有限公司 | 闭门器专用的润滑油及其制备方法 |
| CN112430493B (zh) * | 2019-08-26 | 2022-10-28 | 中国石油化工股份有限公司 | 一种具备难燃性能的闭门器油组合物 |
| CN112159703A (zh) * | 2020-08-28 | 2021-01-01 | 希玛石油制品（镇江）有限公司 | 一种环保水溶性闭门器润滑剂及其制备方法 |
| CN112920873A (zh) * | 2021-01-26 | 2021-06-08 | 宝鸡文理学院 | 一种基于天然产物的合成酯类润滑油基础油 |
| JP2024005098A (ja) * | 2022-06-29 | 2024-01-17 | 出光興産株式会社 | 潤滑油組成物並びにその使用方法及び製造方法 |
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| FI66899C (fi) * | 1983-02-11 | 1984-12-10 | Kasvisoeljy Vaextolje Ab Oy | Smoerjmedel med triglycerider som huvudkomponent |
| JP2558496B2 (ja) | 1988-04-19 | 1996-11-27 | トヨタ自動車株式会社 | 自己消火性を有する作動油 |
| US5250750A (en) * | 1990-07-19 | 1993-10-05 | Ethyl Corporation | Apparatus and oil compositions containing olefin dimer products |
| ES2106085T3 (es) | 1990-08-31 | 1997-11-01 | Olin Corp | Procedimiento para mejorar la resistencia al fuego de un sistema hidraulico. |
| JP2888742B2 (ja) * | 1992-12-07 | 1999-05-10 | 出光興産株式会社 | 難燃性油圧作動油 |
| DE69319884T2 (de) * | 1992-12-07 | 1998-12-10 | Idemitsu Kosan Co | Flammfestes Hydrauliköl |
| US5413725A (en) * | 1992-12-18 | 1995-05-09 | The Lubrizol Corporation | Pour point depressants for high monounsaturated vegetable oils and for high monounsaturated vegetable oils/biodegradable base and fluid mixtures |
| DE69524038T2 (de) * | 1994-10-12 | 2003-04-24 | Rohmax Additives Gmbh | Zusatz für Schmieröl |
| BR9504838A (pt) * | 1994-11-15 | 1997-10-07 | Lubrizol Corp | Ester de poliol composição de óleo lubrificante |
| US5538654A (en) * | 1994-12-02 | 1996-07-23 | The Lubrizol Corporation | Environmental friendly food grade lubricants from edible triglycerides containing FDA approved additives |
| US5658864A (en) * | 1995-03-24 | 1997-08-19 | Ethyl Corporation | Biodegradable pour point depressants for industrial fluids derived from biodegradable base oils |
| US5949017A (en) * | 1996-06-18 | 1999-09-07 | Abb Power T&D Company Inc. | Electrical transformers containing electrical insulation fluids comprising high oleic acid oil compositions |
| JP4730982B2 (ja) * | 1998-03-25 | 2011-07-20 | 出光興産株式会社 | 難燃性油圧作動油 |
| US6383992B1 (en) * | 2000-06-28 | 2002-05-07 | Renewable Lubricants, Inc. | Biodegradable vegetable oil compositions |
| TWI228540B (en) * | 2001-04-06 | 2005-03-01 | Nippon Mitsubishi Oil Corp | Oil composition for very small amount oil supply type cutting and grinding operation |
| MY128504A (en) * | 2001-09-25 | 2007-02-28 | Pennzoil Quaker State Co | Environmentally friendly lubricants |
| KR100855112B1 (ko) * | 2003-09-12 | 2008-08-28 | 리뉴어블 루브리컨츠 인코포레이션 | 전-수소처리된 합성유를 포함하는 식물유계 윤활유 |
| JP4792216B2 (ja) * | 2004-11-01 | 2011-10-12 | Ｊｘ日鉱日石エネルギー株式会社 | 極微量油剤供給式切削・研削加工用油剤組成物 |
| US20070293408A1 (en) * | 2005-03-11 | 2007-12-20 | Chevron Corporation | Hydraulic Fluid Compositions and Preparation Thereof |
| AU2006260922A1 (en) * | 2005-06-23 | 2006-12-28 | Shell Internationale Research Maatschappij B.V. | Electrical oil formulation |
| EP1741770A1 (en) * | 2005-07-04 | 2007-01-10 | Monsanto S.A.S. | Use of rapeseed oil in biolubricants |
| US8168572B2 (en) * | 2007-04-25 | 2012-05-01 | Dow Global Technologies Llc | Lubricant blend composition |
| CA2786816C (en) * | 2007-05-17 | 2014-12-23 | Cooper Industries, Inc. | Vegetable oil dielectric fluid composition |
| US8801975B2 (en) * | 2007-05-17 | 2014-08-12 | Cooper Industries, Llc | Vegetable oil dielectric fluid composition |
| JP5301226B2 (ja) * | 2007-09-26 | 2013-09-25 | 昭和シェル石油株式会社 | 建設機械用作動油 |
| JP5715321B2 (ja) * | 2008-06-09 | 2015-05-07 | 出光興産株式会社 | 潤滑油組成物 |
| DE102009022593A1 (de) * | 2008-06-13 | 2009-12-17 | KLüBER LUBRICATION MüNCHEN KG | Schmierstoffzusammensetzung auf der Basis natürlicher und nachwachsender Rohstoffe |
| CH699659B1 (de) * | 2008-10-14 | 2012-10-15 | Natoil Ag | Hydraulikflüssigkeit und Getriebeöl auf Pflanzenölbasis. |
| FR2939443B1 (fr) * | 2008-12-05 | 2013-01-18 | Total Raffinage Marketing | Huile lubrifiante a base d'esters de polyols |
| EP2616508B1 (en) * | 2010-09-17 | 2014-12-17 | Dow Global Technologies LLC | A thermally-stable dielectric fluid |
-
2010
- 2010-03-31 JP JP2010084472A patent/JP5764298B2/ja active Active
-
2011
- 2011-03-29 CN CN2011800145217A patent/CN102812114A/zh active Pending
- 2011-03-29 EP EP11765579.5A patent/EP2554646B1/en active Active
- 2011-03-29 US US13/637,659 patent/US20130017984A1/en not_active Abandoned
- 2011-03-29 WO PCT/JP2011/057904 patent/WO2011125679A1/ja active Application Filing
- 2011-03-30 TW TW100111031A patent/TWI510611B/zh active
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2554646A1 (en) | 2013-02-06 |
| JP2011213920A (ja) | 2011-10-27 |
| JP5764298B2 (ja) | 2015-08-19 |
| EP2554646A4 (en) | 2013-11-06 |
| TWI510611B (zh) | 2015-12-01 |
| TW201142011A (en) | 2011-12-01 |
| US20130017984A1 (en) | 2013-01-17 |
| CN102812114A (zh) | 2012-12-05 |
| WO2011125679A1 (ja) | 2011-10-13 |
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