EP2850163A1 - Novel low viscosity functional fluid composition - Google Patents
Novel low viscosity functional fluid compositionInfo
- Publication number
- EP2850163A1 EP2850163A1 EP13719518.6A EP13719518A EP2850163A1 EP 2850163 A1 EP2850163 A1 EP 2850163A1 EP 13719518 A EP13719518 A EP 13719518A EP 2850163 A1 EP2850163 A1 EP 2850163A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- functional fluid
- fluid composition
- weight
- component
- composition according
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 239000012530 fluid Substances 0.000 title claims abstract description 51
- -1 alkoxy glycol borate esters Chemical class 0.000 claims abstract description 44
- 239000000654 additive Substances 0.000 claims abstract description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 23
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000005260 corrosion Methods 0.000 claims abstract description 16
- 230000007797 corrosion Effects 0.000 claims abstract description 16
- 230000000996 additive effect Effects 0.000 claims abstract description 12
- 230000005764 inhibitory process Effects 0.000 claims abstract description 11
- 238000009835 boiling Methods 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 230000001747 exhibiting effect Effects 0.000 claims abstract 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 9
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 238000007046 ethoxylation reaction Methods 0.000 description 11
- 102100024737 Deoxynucleotidyltransferase terminal-interacting protein 2 Human genes 0.000 description 10
- 101000626071 Homo sapiens Deoxynucleotidyltransferase terminal-interacting protein 2 Proteins 0.000 description 10
- 150000001642 boronic acid derivatives Chemical class 0.000 description 5
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000006353 oxyethylene group Chemical group 0.000 description 4
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 4
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 2
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003136 n-heptyl 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])* 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- JINYDRJPPUUUIJ-UHFFFAOYSA-N 1-(2-hydroxyethoxy)octan-2-ol Chemical compound CCCCCCC(O)COCCO JINYDRJPPUUUIJ-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- SBGFNHWKIOFPRM-UHFFFAOYSA-N 1-[2-(2-hydroxyethoxy)ethoxy]hexan-2-ol Chemical compound CCCCC(O)COCCOCCO SBGFNHWKIOFPRM-UHFFFAOYSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- YOFPVMWVLDSWKR-UHFFFAOYSA-N 11-methyl-n-(11-methyldodecyl)dodecan-1-amine Chemical compound CC(C)CCCCCCCCCCNCCCCCCCCCCC(C)C YOFPVMWVLDSWKR-UHFFFAOYSA-N 0.000 description 1
- NGKIIKNJVVBNNE-UHFFFAOYSA-N 11-methyldodecan-1-amine Chemical compound CC(C)CCCCCCCCCCN NGKIIKNJVVBNNE-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- OADIZUFHUPTFAG-UHFFFAOYSA-N 2-[2-(2-ethylhexoxy)ethoxy]ethanol Chemical compound CCCCC(CC)COCCOCCO OADIZUFHUPTFAG-UHFFFAOYSA-N 0.000 description 1
- GTAKOUPXIUWZIA-UHFFFAOYSA-N 2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethanol Chemical compound CCOCCOCCOCCOCCO GTAKOUPXIUWZIA-UHFFFAOYSA-N 0.000 description 1
- AVJRDBHYLUZPBA-UHFFFAOYSA-N 2-ethyl-n-methylhexan-1-amine Chemical compound CCCCC(CC)CNC AVJRDBHYLUZPBA-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- HGMSOUSXJSGJKB-UHFFFAOYSA-N 2-propyl-n-(2-propylheptyl)heptan-1-amine Chemical compound CCCCCC(CCC)CNCC(CCC)CCCCC HGMSOUSXJSGJKB-UHFFFAOYSA-N 0.000 description 1
- SSOBBNSVCWLYPH-UHFFFAOYSA-N 2-propylheptan-1-amine Chemical compound CCCCCC(CN)CCC SSOBBNSVCWLYPH-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 1
- ZNYRFEPBTVGZDN-UHFFFAOYSA-N 5S,6S-epoxy-15R-hydroxy-ETE Chemical compound COCCOCCOCCOCCO ZNYRFEPBTVGZDN-UHFFFAOYSA-N 0.000 description 1
- DZDVMKLYUKZMKK-UHFFFAOYSA-N 7-methyloctan-1-amine Chemical compound CC(C)CCCCCCN DZDVMKLYUKZMKK-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- 125000006538 C11 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- 101710171920 Fumarate reductase flavoprotein subunit Proteins 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- NKGSHSILLGXYDW-UHFFFAOYSA-N N-undecylundecan-1-amine Chemical compound CCCCCCCCCCCNCCCCCCCCCCC NKGSHSILLGXYDW-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- ITBPIKUGMIZTJR-UHFFFAOYSA-N [bis(hydroxymethyl)amino]methanol Chemical compound OCN(CO)CO ITBPIKUGMIZTJR-UHFFFAOYSA-N 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
- BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- KXEKJGFTZBVMJZ-UHFFFAOYSA-N n,11-dimethyldodecan-1-amine Chemical compound CNCCCCCCCCCCC(C)C KXEKJGFTZBVMJZ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- RLARTHIKSMHWBL-UHFFFAOYSA-N n-heptadecylheptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCC RLARTHIKSMHWBL-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- NQYKSVOHDVVDOR-UHFFFAOYSA-N n-hexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCC NQYKSVOHDVVDOR-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- CPTXPDMOZQHSFO-UHFFFAOYSA-N n-icosylicosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCCCC CPTXPDMOZQHSFO-UHFFFAOYSA-N 0.000 description 1
- SSQPNZNPMOFMAR-UHFFFAOYSA-N n-methyl-2-propylheptan-1-amine Chemical compound CCCCCC(CCC)CNC SSQPNZNPMOFMAR-UHFFFAOYSA-N 0.000 description 1
- IKVDMBQGHZVMRN-UHFFFAOYSA-N n-methyldecan-1-amine Chemical compound CCCCCCCCCCNC IKVDMBQGHZVMRN-UHFFFAOYSA-N 0.000 description 1
- OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 1
- OHZXFIXUSZRHAB-UHFFFAOYSA-N n-methylheptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCNC OHZXFIXUSZRHAB-UHFFFAOYSA-N 0.000 description 1
- LTGYRKOQQQWWAF-UHFFFAOYSA-N n-methylheptan-1-amine Chemical compound CCCCCCCNC LTGYRKOQQQWWAF-UHFFFAOYSA-N 0.000 description 1
- IHFXMTOFDQKABX-UHFFFAOYSA-N n-methylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNC IHFXMTOFDQKABX-UHFFFAOYSA-N 0.000 description 1
- XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
- LYFMJSSIPHXUEN-UHFFFAOYSA-N n-methylicosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCNC LYFMJSSIPHXUEN-UHFFFAOYSA-N 0.000 description 1
- FHIVPSFDDZPTIS-UHFFFAOYSA-N n-methylnonadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCNC FHIVPSFDDZPTIS-UHFFFAOYSA-N 0.000 description 1
- OZIXTIPURXIEMB-UHFFFAOYSA-N n-methylnonan-1-amine Chemical compound CCCCCCCCCNC OZIXTIPURXIEMB-UHFFFAOYSA-N 0.000 description 1
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
- SEGJNMCIMOLEDM-UHFFFAOYSA-N n-methyloctan-1-amine Chemical compound CCCCCCCCNC SEGJNMCIMOLEDM-UHFFFAOYSA-N 0.000 description 1
- CNCBAEHAEKNSPZ-UHFFFAOYSA-N n-methylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNC CNCBAEHAEKNSPZ-UHFFFAOYSA-N 0.000 description 1
- QWERMLCFPMTLTG-UHFFFAOYSA-N n-methyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCNC QWERMLCFPMTLTG-UHFFFAOYSA-N 0.000 description 1
- XMRPIOZXPHTSCE-UHFFFAOYSA-N n-methyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNC XMRPIOZXPHTSCE-UHFFFAOYSA-N 0.000 description 1
- JCJFBKCQLFMABE-UHFFFAOYSA-N n-methylundecan-1-amine Chemical compound CCCCCCCCCCCNC JCJFBKCQLFMABE-UHFFFAOYSA-N 0.000 description 1
- UQLQVWLBTRWAIP-UHFFFAOYSA-N n-nonadecylnonadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCCC UQLQVWLBTRWAIP-UHFFFAOYSA-N 0.000 description 1
- MFHKEJIIHDNPQE-UHFFFAOYSA-N n-nonylnonan-1-amine Chemical compound CCCCCCCCCNCCCCCCCCC MFHKEJIIHDNPQE-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- YDFFPEXFCAUTSL-UHFFFAOYSA-N n-pentadecylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNCCCCCCCCCCCCCCC YDFFPEXFCAUTSL-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- HSUGDXPUFCVGES-UHFFFAOYSA-N n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCNCCCCCCCCCCCCCC HSUGDXPUFCVGES-UHFFFAOYSA-N 0.000 description 1
- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- INAMEDPXUAWNKL-UHFFFAOYSA-N nonadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCN INAMEDPXUAWNKL-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- BYRJZJXBVKUYFH-UHFFFAOYSA-N tris[2-[2-(2-methoxyethoxy)ethoxy]ethyl] borate Chemical compound COCCOCCOCCOB(OCCOCCOCCOC)OCCOCCOCCOC BYRJZJXBVKUYFH-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
- C10M2209/1085—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
-
- 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
- C10M2227/0615—Esters derived from boron used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- the present invention relates to a low viscosity functional fluid composition
- a low viscosity functional fluid composition comprising (A) from 15 to 90% by weight, based on the weight of the total composition, of one or more alkoxy glycol borate esters having the general formula (I)
- R 1 is a Ci- to C 4 -alkyl radical or a mixture of such radicals and value of from 2 to 6, from 5 to 80% by weight, based on the weight of the total composition, of or more alkoxy glycol components having the general formula (II)
- R 2 -0-(CH 2 CH 2 -0) m -H (II) wherein R 2 is a Ci- to Cs-alkyl radical or a mixture of such radicals and m has a value of from 2 to 6, R 2 and/or m being different or identical to R 1 and/or n, respectively, from 0.1 to 10% by weight, based on the total weight of the composition, of an additive package comprising one or more additives with corrosion inhibition action, wherein at least one of the additives contained in the additive package of component (C) is selected from alkylamine ethoxylates.
- the said low viscosity functional fluid composition is useful in a variety of applications and in particular as a brake fluid, especially for new electronic or automated anti-lock brake systems which require lower viscosity fluids for satisfactory operation at low temperatures.
- borate esters are well known in the art.
- these borate ester based compositions must meet stringent physical properties and performance requirements particularly with respect to minimum dry equilibrium reflux boiling point (“ERBP”), minimum wet equilibrium reflux boiling point (“WERBP”) and maximum low temperature kinematic viscosity (e.g. determined at -40°C) while maintaining adequate resistance to corrosion, stability and meeting other physical property requirements such as pH, reserve alkalinity and rubber swell.
- ERBP dry equilibrium reflux boiling point
- WERBP minimum wet equilibrium reflux boiling point
- maximum low temperature kinematic viscosity e.g. determined at -40°C
- WO 00/65001 describes hydraulic fluids comprising alkoxy glycol borate esters, alkoxy glycols and corrosions inhibitors, further containing cyclic carboxylic acid derivatives.
- WO 02/3871 1 describes low viscosity functional fluid compositions comprising alkoxy glycol borate esters, alkoxy glycol components and additives such as corrosion inhibitors, wherein the alkoxylation degrees of the alkoxy glycol borate esters and the alkoxy glycols are restricted to a certain narrow pattern.
- the above-defined functional fluid composition has been found which exhibits superior values of ERBP and of WERBP and for low temperature kinematic viscosity while maintaining excellent resistance to corrosion, high stability and meeting other physical property requirements such as pH, reserve alkalinity and rubber swell. Especially very high WERBP values are achieved. Moreover, kinematic viscosity value at very low temperatures below -40°C, e.g. at -50°C, are superior compared to functional fluid compositions of the art.
- the alkylamine ethoxylates as part of component (C) and their interaction with the other components and additives of the present functional fluid composition are deemed to be responsible for the superior performance and especially for the very high WERBP values.
- the alkylamine residue in the said alkylamine ethoxylates may be a secondary or preferably a primary aliphatic monoamine which is capable of being ethoxylated.
- alkyl residues to the nitrogen atom normally comprise saturated linear or branched alkyl groups, however, unsaturated linear or branched alkyl residues or saturated or unsaturated cycloalkyl residues may also be comprised by the term "alkyl”.
- the said alkylamine ethoxylates comprise at least one linear or branched C3 to C20 alkyl chain, preferably at least one linear or branched C6 to Ci3 alkyl chain, more preferably at least one linear or branched C7 to C12 alkyl chain, most preferably at least one linear or branched Cs to Cn alkyl chain.
- the term "alkyl chain” here means saturated and non-cyclic hydrocarbon residues.
- the alkylamine ethoxylates may also comprise mixtures of such alkyl chains, for example a mixture of homologue alkyl residues, depending on the specific technical or natural origin of the alkylamines used.
- Suitable examples for single alkylamine molecules being capable for ethoxylation and, therefore, suitable as surfactants for the instant invention are n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, tert-butylamine, n-pentyl- amine, tert-pentylamine, n-hexylamine, n-heptylamine, n-octylamine, 2-ethylhexyl- amine, n-nonylamine, n-decylamine, 2-propylheptylamine, n-undecylamine, n-dodecyl- amine, n-tridecylamine, isotridecylamine, n-tetradecylamine, n-pentadecylamine, n- hexadecylamine, n-heptadec
- alkyl residues may be derived entirely from petrochemical production, for example technical Cs-C-is alkyl mixtures, 2-ethylhexyl or 2-propylheptyl, or may entirely or partially be based on renewable raw materials, for example fatty amines such as stearyl amine, oleyl amine or tallow amine may be used as the basis for the alkylamine ethoxylates.
- the degree of ethoxylation is usually from 1 to 35 EO units per alkylamine molecule, i.e.
- the at least on alkylamine ethoxylate comprises from 1 to 35 EO units, preferably from 1.5 to 15 EO units, more preferable from 1 .8 to 9 EO units, most preferably from 2 to 6 EO units.
- the said ethoxylation degree is a statistical value, i.e the alkylamine ethoxylates have normally to be regardes as mixtures of species (homologues) with different numbers of EO units.
- the at least one alkylamine ethoxylate comprises at least on linear C3 to C20 alkyl chain and from 1 to 35 EO units; more preferably the at least one alkylamine ethoxylate comprises at least on linear Ce to C13 alkyl chain and from 1 .5 to 15 EO units; most preferably the at least one alkylamine ethoxylate comprises at least one linear C7 to C12 alkyl chain and from 1 .8 to 9 EO units, especially the at least one alkylamine ethoxylate comprises at least one linear Cs to Cn alkyl chain and from 2 to 6 EO units.
- Such alkylamine ethoxylates may be primary amines with one oxyethylene chain of general formula Alkyl-NH-(CH2CH20) m -H or primary amines with two oxyethylene chains of general formula Alkyl-N[(CH2CH20) p -H][(CH2CH20) q -H] or secondary amines of general formula (Alkyl)2N-(CH2CH20) m -H or mixtures of such primary amines with one oxyethylene chain and such primary amines with two oxyethylene chains or mixtures of such primary and secondary amines, wherein m and (p+q), respectively, are the total ethoxylation degrees.
- Alkyl in the above formulas normally means C3 to C20 alkyl, preferably C6 to C13 alkyl, more preferably C7 to C12 alkyl, most preferably C& to C11 alkyl, as defined above. Residual alkylamine species may also be present in lower amounts, especially with low total ethoxylation degrees below 2.
- a typical suitable alkylamine ethoxylate is octylamine (caprylamine) with 2 EO units which is commercially available.
- the said alkylamine ethoxylates can be prepared by usual methods such as the reaction of the alkylamine with ethylene oxide under catalysis by alkali metal hydroxides or under catalysis by double metal cyanides, as known to the skilled person in the art.
- the said alkylamine ethoxylates has partly corrosion inhibition properties and partly solvent properties for the functional fluid composition or brake fluid, respectively, according to the present invention.
- Component (A) may be a single species or a mixture of different species with regard to the ethoxylation degree and/or to radical R 1 .
- Radical R 1 is preferably a Ci- to C 4 -alkyl radical and may be methyl, ethyl, n-propyl, isopropyl, n- butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl and 2-ethylhexyl, ethyl and especially methyl being preferred.
- Borate esters especially useful in the functional fluid composition of the present invention may be prepared by reacting boric acid with suitable alkoxy glycol components which are different or identical to those of component (B). Typically, such alkoxy glycol components are mixtures of different species with regard to the ethoxylation degree and/or to radical R 1 .
- borate esters examples include those containing methyl triethylene glycol borate ester which can also be named tris-[2-[2-(2-methoxyethoxy)-ethoxy]-ethyl) orthoborate, ethyl triethylene glycol borate ester, n-butyl triethylene glycol borate ester and mixtures thereof.
- borate esters include those containing methyl tetraethylene glycol borate ester, methyl diethylene glycol borate ester, ethyl tetraethylene glycol borate ester, ethyl diethylene glycol borate ester, n-butyl tetraethylene glycol borate ester, n-butyl diethylene glycol borate ester and mixtures thereof.
- Component (B) may be a single species or a mixture of different species with regard to the ethoxylation degree and/or to radical R 2 .
- Radical R 2 is preferably a Ci- to C 4 -alkyl radical and may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert- butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl and 2-ethylhexyl, ethyl and especially methyl being preferred.
- Examples of useful alkoxy glycols for component (B) of the present invention include methyldiglycol, methyltriglycol, methyltetraglycol, methylpentaglycol, methylhexaglycol, ethyldiglycol, ethyltriglycol, ethyltetraglycol, ethylpentaglycol, ethylhexaglycol, n-propyl- diglycol, n-propyltriglycol, n-propyltetraglycol, n-propylpentaglycol, n-propylhexaglycol, n-butyldiglycol, n-butyltriglycol, n-butyltetraglycol, n-butylpentaglycol, n-butylhexaglycol, n-pentyldiglycol, n-pentyltriglycol, n-pentylt
- the weight ratio of methyltriglycol to n-butyltriglycol in this mixture is from 5 : 1 to 1 : 2, especially from 2 : 1 to 1 : 1.
- Component (C) of the present functional fluid composition may comprise, besides the alkylamine ethoxylates, at least one additive with corrosion inhibition action, although the alkylamine ethoxylates exhibit corrosion inhibition properties themselves.
- Suitable customary additives with corrosion inhibition properties include fatty acids such as lauric, palmitic, stearic or oleic acid; esters of phosphorus or phosphoric acid with aliphatic alcohols; phosphites such as ethyl phosphate, dimethyl phosphate, isopropyl phosphate, n-butyl phosphate, triphenyl phosphite and diisopropyl phosphite; heterocyclic nitrogen containing organic compounds such as benzotriazole, tolutriazole, 1 ,2,4- triazole, benzoimidazole, purine, adenine and derivatives of such heterocyclic organic compounds; alkylamines such as mono- and di-(C 4 - to C2
- n-butyl- amine n-hexylamine, n-octylamine, 2-ethylhexylamine, isononylamine, n-decylamine, n-dodecylamine, oleylamine, d-n-proylamine, di-isopropylamine, di-ni-butylamine, di-n- amylamine, cyclohexylamine and salts of such alkylamines; alkanolamines such as mono-, di- and trimethanolamine, mono-, di- and triethanolamine, mono-, di- and tri-n- propanolamine and mono-, di- and tri-isopropanolamine.
- mixtures of the above additives with corrosion inhibition action can be used.
- alkylamines and/or alkanolamines as compounds with corrosion inhibition action in the additive package of component (C) often results in an additional decrease in viscosity of the present functional fluid composition.
- additives may be present in the additive package of component (C), for example stabilizers such as pH stabilizers, antioxidants such as phenol- thiazine and phenolic compounds, e.g. hydroxyanisol and bisphenol A, defoamers and dyes.
- stabilizers such as pH stabilizers
- antioxidants such as phenol- thiazine and phenolic compounds, e.g. hydroxyanisol and bisphenol A, defoamers and dyes.
- the additive package of component (C) which includes one or more alkylamine ethoxylates consists or consists essentially of a major portion of additives with corrosion inhibition action and a minor portion of additives with antioxidant action and possibly of defoamers and dyes.
- the portion of alkylamine ethoxylate(s) in the additive package of component (C) is typically of from 1 to 100% by weight, preferably of from 10 to 99% by weight, more preferably of from 25 to 98% by weight, most preferably of from 40 to 97% by weight, each based on the weight of the additive package of component (C).
- the present functional fluid composition may include from 0 to 20% by weight, based on the total weight of the composition, of a diluent or a lubricant such as, for example, polyethylene oxides, polypropylene oxides, poly(C 4 - to Cio-alkylene) oxides, dialkoxyglycols or borate co-esters.
- a diluent or a lubricant such as, for example, polyethylene oxides, polypropylene oxides, poly(C 4 - to Cio-alkylene) oxides, dialkoxyglycols or borate co-esters.
- the three components (A), (B) and (C) are present in the functional fluid composition in the following amouts: (A) from 15 to 90% by weight, preferably from 30 to 75% by weight, more preferably from 45 to 65% by weight, most preferably from 56 to 62% by weight; (B) from 5 to 80% by weight, preferably from 20 to 65% by weight, more preferably from 32 to 52% by weight, most preferably from 36 to 42% by weight;
- (C) from 0.1 to 10% by weight, preferably from 0.5 to 7% by weight, more preferably from 1 to 4% by weight, most preferably from 1.5 to 2.5% by weight.
- All % values for (A), (B) and (C) above refer to the total composition of the present functional fluid composition, or - if other materials than components (A), (B) and (C), e.g. the above-mentioned diluents and/or lubricants, are present - to the total weight of (A) plus (B) plus (C).
- the % values for (A), (B) and (C) add up in each case to 100% by weight.
- the functional fluid composition of the present invention exhibits superior behavior in ERBP and WERBP temperature and simultaneously in low temperature viscosity performance.
- it exhibits a ERBP of at least 260°C, more preferably of at least 265°C, most preferably of at least 270°C, and/or a WERBP of at least 180°C, more preferably of at least 182°C, still more preferably of at least 184°C, most preferably of at least 187°C.
- cSt centistokes
- the functional fluid composition of the present invention exhibits a low temperature kinematic viscosity of preferably less than 4000 cSt, more preferably of less than 3000 cSt, most preferably less than 2600 cSt, each determined at a temperature of -50°C, whereas typical functional fluid compositions of the art exhibit low temperature kinematic viscosities in the region from about 4500 cSt to about 6000 cSt at -50°C.
- the low viscosity functional fluid composition of the present invention is especially useful as a brake fluid, for example for vehicles such as passenger cars and trucks, especially for new electronic or automated anti-lock brake systems which require lower viscosity fluids for satisfactory operation at low temperatures.
- the functional fluid composition of the present invention exhibits a good corrosion protection, a good water compatibility, a mild pH value, a good stability with regard to low and high temperatures, a good oxidation stability, a good chemical stability, a good behavior towards rubber and elastomers and a good lubrication performance.
- the following examples are intended to demonstrate the behavior and performance of the low temperature functional fluid composition of the present invention without limiting it.
- FFC1 The ERBP and WERBP temperatures and kinematic viscosity values of the following function fluid compositions according to the present invention
- FFC2 The ERBP and WERBP temperatures and kinematic viscosity values of the following function fluid compositions according to the present invention
- FFC3 the corresponding values of Example 8 of WO 02/3871 1
- WERPB i.e. 186°C
- compositions of FFC1 , FFC2 and FFC3 [% by weight]
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
Description
Claims
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EP13719518.6A EP2850163B1 (en) | 2012-05-15 | 2013-04-25 | Novel low viscosity functional fluid composition |
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EP12167986 | 2012-05-15 | ||
EP13719518.6A EP2850163B1 (en) | 2012-05-15 | 2013-04-25 | Novel low viscosity functional fluid composition |
PCT/EP2013/058664 WO2013171052A1 (en) | 2012-05-15 | 2013-04-25 | Novel low viscosity functional fluid composition |
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EP2850163A1 true EP2850163A1 (en) | 2015-03-25 |
EP2850163B1 EP2850163B1 (en) | 2019-03-06 |
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EP (1) | EP2850163B1 (en) |
JP (1) | JP2015516495A (en) |
KR (1) | KR20150008189A (en) |
CN (1) | CN104302747B (en) |
BR (1) | BR112014028179A2 (en) |
CA (1) | CA2871544A1 (en) |
ES (1) | ES2728662T3 (en) |
WO (1) | WO2013171052A1 (en) |
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US10669503B2 (en) | 2014-02-25 | 2020-06-02 | Jon A. Petty | Corrosion inhibiting hydraulic fluid additive |
CA2939801A1 (en) | 2014-02-25 | 2015-09-03 | Jon A. Petty | Corrosion inhibiting hydraulic fluid additive |
CN106190450B (en) * | 2016-06-27 | 2019-07-16 | 辽宁道博精细化学品生产有限公司 | A kind of alcohol ether borate type braking fluid |
CN106190451A (en) * | 2016-06-27 | 2016-12-07 | 辽宁道博精细化学品生产有限公司 | A kind of preparation method of alcohol ether borate type braking fluid |
CN107573998B (en) * | 2017-09-28 | 2021-02-02 | 张家港迪克汽车化学品有限公司 | DOT6 borate type brake fluid |
KR102618845B1 (en) * | 2020-04-23 | 2023-12-29 | 클라리언트 인터내셔널 리미티드 | Low viscosity functional fluid composition |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL302392A (en) * | 1962-12-28 | |||
US3637794A (en) * | 1967-04-13 | 1972-01-25 | Olin Mathieson | Borate esters prepared by successive reactions of boric acid with glycol monoethers and polyols |
JPS5213596B2 (en) * | 1973-12-03 | 1977-04-15 | ||
JPS5930759B2 (en) * | 1977-05-31 | 1984-07-28 | 三洋化成工業株式会社 | Novel brake fluid composition |
DE2945094A1 (en) * | 1979-11-08 | 1981-05-21 | Hoechst Ag, 6000 Frankfurt | HYDRAULIC LIQUID WITH IMPROVED PROPERTIES |
FR2702772B1 (en) * | 1993-03-17 | 1995-04-28 | Bp Chemicals Snc | Hydraulic fluid composition. |
FR2735784B1 (en) * | 1995-06-23 | 1997-08-22 | Bp Chemicals Snc | HYDRAULIC FLUID COMPOSITION COMPRISING A CORROSION INHIBITOR SYSTEM |
DE19546856C1 (en) * | 1995-12-15 | 1997-06-26 | Hoechst Ag | Test procedure for hydraulic fluids based on glycols and glycol boric acid esters with regard to precipitation tendency |
DE19918199A1 (en) | 1999-04-22 | 2000-10-26 | Basf Ag | Hydraulic fluid, especially motor vehicle brake fluid, contains one or more cyclic esters or amides of carboxylic acids, e.g. N-methyl-pyrrolidone |
US6558569B1 (en) | 2000-11-10 | 2003-05-06 | Union Carbide Chemicals & Plastics Technology Corporation | Low viscosity functional fluids compositions |
US6843916B2 (en) * | 2002-07-16 | 2005-01-18 | The Lubrizol Corporation | Slow release lubricant additives gel |
KR20080025192A (en) * | 2005-07-01 | 2008-03-19 | 다우 글로벌 테크놀로지스 인크. | Low viscosity functional fluid |
US20080015126A1 (en) * | 2006-07-12 | 2008-01-17 | Teresan W. Gilbert | Ashless Controlled Release Gels |
US20090088349A1 (en) * | 2007-09-28 | 2009-04-02 | Dow Global Technologies Inc. | Functional fluid composition |
CN102971404B (en) * | 2010-07-01 | 2014-09-24 | 陶氏环球技术有限责任公司 | Low viscosity functional fluids |
-
2013
- 2013-04-25 EP EP13719518.6A patent/EP2850163B1/en active Active
- 2013-04-25 JP JP2015511978A patent/JP2015516495A/en not_active Withdrawn
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- 2013-04-25 CN CN201380025690.XA patent/CN104302747B/en active Active
- 2013-04-25 ES ES13719518T patent/ES2728662T3/en active Active
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CN104302747B (en) | 2016-12-28 |
JP2015516495A (en) | 2015-06-11 |
ES2728662T3 (en) | 2019-10-28 |
BR112014028179A2 (en) | 2017-06-27 |
EP2850163B1 (en) | 2019-03-06 |
WO2013171052A1 (en) | 2013-11-21 |
CN104302747A (en) | 2015-01-21 |
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