EP0239536B1 - Schmiermittelzusammensetzungen - Google Patents
Schmiermittelzusammensetzungen Download PDFInfo
- Publication number
- EP0239536B1 EP0239536B1 EP87810152A EP87810152A EP0239536B1 EP 0239536 B1 EP0239536 B1 EP 0239536B1 EP 87810152 A EP87810152 A EP 87810152A EP 87810152 A EP87810152 A EP 87810152A EP 0239536 B1 EP0239536 B1 EP 0239536B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- bis
- component
- tert
- composition according
- hydroxyethyl
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 58
- 239000000314 lubricant Substances 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 1-[N,N-bis(2-hydroxyethyl)amino]-2-hydroxypropyl Chemical group 0.000 claims description 26
- 238000005260 corrosion Methods 0.000 claims description 16
- 230000007797 corrosion Effects 0.000 claims description 16
- 230000003078 antioxidant effect Effects 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 14
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- LUKIFOVSRKGAMG-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]-3-(6-methylheptoxy)propan-2-ol Chemical compound CC(C)CCCCCOCC(O)CN(CCO)CCO LUKIFOVSRKGAMG-UHFFFAOYSA-N 0.000 claims description 4
- AVBBHCMDRGQBNW-UHFFFAOYSA-N 2-ethyl-n-(2-ethylhexyl)-n-(1,2,4-triazol-1-ylmethyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)CN1C=NC=N1 AVBBHCMDRGQBNW-UHFFFAOYSA-N 0.000 claims description 4
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000010688 mineral lubricating oil Substances 0.000 claims description 4
- 239000002530 phenolic antioxidant Substances 0.000 claims description 4
- 230000006641 stabilisation Effects 0.000 claims description 4
- 238000011105 stabilization Methods 0.000 claims description 4
- UVEXVMUTHAZSNB-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]dodecan-2-ol Chemical compound CCCCCCCCCCC(O)CN(CCO)CCO UVEXVMUTHAZSNB-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229940059904 light mineral oil Drugs 0.000 claims description 3
- 239000006078 metal deactivator Substances 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- JFPNAUDFJSIIQV-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]-3-[2,4-di(propan-2-yl)phenoxy]propan-2-ol Chemical compound CC(C)C1=CC=C(OCC(O)CN(CCO)CCO)C(C(C)C)=C1 JFPNAUDFJSIIQV-UHFFFAOYSA-N 0.000 claims description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 239000003350 kerosene Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- OKQVTLCUHATGDD-UHFFFAOYSA-N n-(benzotriazol-1-ylmethyl)-2-ethyl-n-(2-ethylhexyl)hexan-1-amine Chemical compound C1=CC=C2N(CN(CC(CC)CCCC)CC(CC)CCCC)N=NC2=C1 OKQVTLCUHATGDD-UHFFFAOYSA-N 0.000 claims description 2
- IQYDSMJRFWLGKA-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]-3-(4-nonylphenoxy)propan-2-ol Chemical compound CCCCCCCCCC1=CC=C(OCC(O)CN(CCO)CCO)C=C1 IQYDSMJRFWLGKA-UHFFFAOYSA-N 0.000 claims 1
- LUTMOSWXQHQGSH-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]-3-(4-tert-butylphenoxy)propan-2-ol Chemical compound CC(C)(C)C1=CC=C(OCC(O)CN(CCO)CCO)C=C1 LUTMOSWXQHQGSH-UHFFFAOYSA-N 0.000 claims 1
- ZLNOIWOYJIQYTC-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]-3-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]propan-2-ol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCC(O)CN(CCO)CCO)C=C1 ZLNOIWOYJIQYTC-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 9
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002270 dispersing agent Substances 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- IMXRBCGZTVENAC-UHFFFAOYSA-N n-phenyl-n-(2,4,4-trimethylpentan-2-yl)aniline Chemical class C=1C=CC=CC=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 IMXRBCGZTVENAC-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 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 description 2
- 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 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 150000003254 radicals Chemical group 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
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000010723 turbine oil Substances 0.000 description 2
- 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 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- LCWDWRKWLVEBSS-UHFFFAOYSA-N 2-[6-methylheptoxy-[6-methylheptoxy(oxiran-2-yl)methoxy]methyl]oxirane Chemical compound C(CCCCC(C)C)OC(C1CO1)OC(C1CO1)OCCCCCC(C)C LCWDWRKWLVEBSS-UHFFFAOYSA-N 0.000 description 1
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VCOONNWIINSFBA-UHFFFAOYSA-N 4-methoxy-n-(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(OC)C=C1 VCOONNWIINSFBA-UHFFFAOYSA-N 0.000 description 1
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 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 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- CVVFFUKULYKOJR-UHFFFAOYSA-N n-phenyl-4-propan-2-yloxyaniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1 CVVFFUKULYKOJR-UHFFFAOYSA-N 0.000 description 1
- 150000004950 naphthalene Chemical class 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010736 steam turbine oil 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 150000003568 thioethers Chemical class 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
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbased sulfonic acid salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2223/041—Triaryl phosphates
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2223/043—Ammonium or amine salts thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2223/045—Metal containing thio derivatives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- the present invention relates to corrosion inhibiting lubricating oil compositions, particularly corrosion inhibiting compositions, which also prevent oxidation of the lubricants used to lubricate metal parts in steam turbines.
- oils used to lubricate steam turbines are subject to oxidative degradation at elevated temperatures, which leads to the formation of sludge and an increase in the acidity of the oil.
- EP-A-206998 discloses glucamine derivatives which can be used, inter alia, as stabilizers in lubricants and which can optionally also be used in combination with phenolic antioxidants, amine antioxidants and metal passivators.
- compositions of the present invention meet the requirements for turbine oils with regard to both corrosion-inhibiting and antioxidative properties.
- the compounds of the formula I can be prepared, for example, by reacting a compound of the formula R 1 -XH, in which R 1 and X have the above meaning, with epichlorohydrin, optionally in the presence of a catalyst such as, for example, an acid, base or phase transfer catalyst, a compound of formula arises, which is then reacted with an amine of the formula HNR2R3 with R2 and R3 in the above meaning and thus a compound of formula I is obtained.
- a catalyst such as, for example, an acid, base or phase transfer catalyst
- Component (B) is preferably a compound of the general formula II, wherein R4 is hydrogen or straight-chain or branched C1-C12, preferably C1-C4, alkyl, or is a mixture of compounds of formula II.
- Component (C) is preferably a compound of the general formula III wherein R5 and R6 independently of one another are hydrogen, straight-chain or branched C1-C12-alkyl, a styryl, methoxy or isopropoxy group, or is a mixture of compounds of the formula III.
- Antioxidant mixtures of phenolic and amine types or of different phenolic or different amine types can be used, but mixtures of phenolic and amine types are preferred.
- Component (D) is preferably a compound of the general formula IV, wherein E is hydrogen or a radical of the formula -CH2NR7R8 and R7 and R8 independently of one another are C1-C18 alkyl or C2-C18 alkenyl, and which, for example, by reaction of a 1,2,4-triazole with formaldehyde and an amine Formula HNR7R8 can be prepared, or the general formula V, wherein J represents an N atom or a CH2 group, F together with the C atoms to which F is attached forms a six-membered aromatic or reduced tetrahydroring, which rings may optionally be alkyl-substituted, furthermore where G is hydrogen or a radical of the formula -CH2NR9R10 and R9 and R10 independently of one another represent C1-C18 alkyl or C2-C18 alkenyl, and which, for example, by reaction of a corresponding azole compound with formaldehyde and an amine of the formula H
- component (D) can e.g. also be the reaction product of a 1,2,4-triazole with a zinc bis (0,0'-dialkyldithiophosphate).
- R4, R5, R6 or the substituents of the phenyl radical R1 are straight-chain or branched C1-C12 alkyl, it is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert . -Butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl.
- R7, R8, R9 or R1 dar represent straight-chain or branched C1-C18-alkyl, it is e.g. around methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl , Pentadecyl, hexadecyl, heptadecyl or octadecyl.
- R beutton, R8, R9 or R10 are preferably straight-chain or branched C4-C12-alkyl.
- R7, R8, R9 or R10 represent straight-chain or branched C2-C18 alkenyl, for example vinyl, allyl, n-butenyl, isopentenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, Tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl or oleyl.
- alkenyl for example vinyl, allyl, n-butenyl, isopentenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, Tridecenyl, tetradecenyl, pentadecenyl, he
- R beutton, R8, R9 or R10 are preferably C2-C6-alkenyl or oleyl.
- Particularly preferred compounds of the formula I are: N- (2-hydroxydodecyl) diethanolamine 1- [N, N-bis (2-hydroxyethyl) amino] -3-isooctyloxypropan-2-ol 1- [N, N-bis (2-hydroxyethyl) amino] -3- (tert-nonylthio) propan-2-ol 1- [N, N-bis (2-hydroxyethyl) amino] -2-hydroxypropyl-3- (tert-decanoate) 1- [N, N-Bis (2-hydroxyethyl) amino] -3- (4-nonylphenoxy) propan-2-ol 1- [N, N-Bis (2-hydroxyethyl) amino] -3- (4-tert-butylphenoxy) propan-2-ol 1- [N, N-Bis (2-hydroxyethyl) amino] -3- (2,4-diisopropylphenoxy) propan-2-ol 1- [N, N, -
- Particularly preferred compounds of the formula II are: 2,6-di-tert-butylphenol 2,6-di-tert-4-methylphenol or mixtures thereof.
- Particularly preferred compounds of the formula III are: Di- (tert-octylated) diphenylamine or a mixture of mono- and dialkylated tert-butyl / tert-octyldiphenylamines.
- Benzotriazole Tetrahydrobenztriazole Tolutriazole Benzimidazole 1,2,4-triazole 1- [N, N-Bis (2-ethylhexyl) aminomethyl] benzotriazole 1- [N, N-Bis (2-ethylhexyl) aminomethyl] tolutriazole 1- [N, N-Bis (2-ethylhexyl) aminomethyl] benzimidazole 1- [N, N-Bis (2-ethylhexyl) aminomethyl] 1,2,4-triazole Product of the reaction of 1,2,4-triazole with zinc bis [0.0 ⁇ -di- (2-ethylhexyl) dithiophosphate].
- Particularly preferred compounds of the formulas IV and V are: 1- [N, N-Bis (2-ethylhexyl) aminomethyl] benzotriazole 1- [N, N-Bis (2-ethylhexyl) aminomethyl] tolutriazole 1- [N, N-Bis (2-ethylhexyl) aminomethyl] 1,2,4-triazole Product of the reaction of 1,2,4-triazole with zinc bis [0.0 ⁇ -di- (2-ethylhexyl) dithiophosphate].
- the weight ratios of components (A), (B), (C) and (D) in the compositions according to the invention can change depending on the type of application and the degree of corrosion inhibition and antioxidative stabilization required. In general, however, the ratios are preferred as follows.
- Component A 0.02-0.10% by weight, preferably 0.02-0.05% by weight;
- Component B 0.05-0.25% by weight, preferably 0.05-0.15% by weight;
- Component C 0.02-0.10% by weight, preferably 0.03-0.06% by weight;
- Component D 0.02-0.10% by weight, preferably 0.03-0.06% by weight, always based on the total weight of the lubricant composition.
- Components (A) to (D) can be added to the lubricating oil individually. However, they are preferably premixed in the form of a basic mixture, which is then added to the lubricating oil.
- the basic mixture is added to the oil in an amount sufficient to meet the requirements regarding the degree of corrosion inhibition and the antioxidative stabilization.
- the use of the components in the form of a premixed concentrate gives advantages in terms of storage, transportation and addition to the oil.
- the additive concentrate according to the invention can be diluted as desired with a suitable inert solvent, such as, for example, a light mineral oil, a kerosene or an aromatic hydrocarbon.
- a suitable inert solvent such as, for example, a light mineral oil, a kerosene or an aromatic hydrocarbon.
- concentration of the additive concentrate is limited by the solubility of components (A) to (D) in the diluent, but in general a concentration of 60% by weight of active substances is easily achieved in a light mineral oil.
- the invention also relates to the use of an additive concentrate according to the invention composed of (A), (B), (C) and (D) (with the above stipulations) for corrosion inhibition and antioxidative stabilization of mineral lubricating oils.
- the lubricant compositions according to the invention can contain, in addition to components (A), (B), (C) and (D), one or more further additives which are usually used in lubricant compositions in order to further improve their basic properties, e.g. Viscosity index improvers, pour point depressants, dispersants / surfactants or high pressure / wear protection additives.
- one or more further additives which are usually used in lubricant compositions in order to further improve their basic properties, e.g. Viscosity index improvers, pour point depressants, dispersants / surfactants or high pressure / wear protection additives.
- viscosity index improvers examples are e.g.
- Polymethacrylates vinyl pyrrolidone / methacrylate copolymers, polybutenes, olefin copolymers, styrene / acrylate copolymers.
- pour point depressants examples include:
- dispersants / surfactants examples include:
- Polybutenylsuccinic acid imides polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.
- wear protection additives examples include:
- Compounds containing sulfur and / or phosphorus and / or halogen such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl disulfides.
- This compound is prepared by reacting 1,2-epoxydodecane with diethanolamine as described in US Pat. No. 2,856,363.
- a mixture of 69 parts of 1,2,4-triazole and 771 parts of zinc bis- [0.0 ⁇ -di- (2-ethylhexyl) dithiophosphate] is gradually heated to 95 ° C. with stirring. After stirring for 30 minutes at this temperature, the product becomes a clear liquid. Stirring is continued until the product has cooled to room temperature.
- the end product (D2) is a clear, yellow oil.
- the additive compositions are prepared by mixing the specific components in the weight ratios shown in Table 1.
- compositions of Examples 7 to 17 containing components (A) to (D) are used as corrosion inhibitors in a turbine mineral oil with a viscosity of 22 mPa s at 40 ° C and 3.8 mPa s at 100 ° C and a sulfur content of 0 , 6% tested according to the ASTM D-665B test.
- the results are shown in Table 1 and indicate the concentration of the components which prevent any rust from forming on the test spindle.
- the compositions are also tested for their antioxidant activity in a modified ASTM D-943 test. The results reflect the amount of sludge (oxidation products) that formed after 500 hours. In general, an oil composition with good antioxidant properties shows the formation of less than 50 mg of sludge after the test period.
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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)
- Lubricants (AREA)
Description
- Die vorliegende Erfindung betrifft korrosionsinhibierende Schmierölzusammensetzungen, insbesondere korrosionsinhibierende Zusammensetzungen, die ebenfalls die Oxidation der Schmiermittel verhindern, welche zur Schmierung von Metallteilen in Dampfturbinen verwendet werden.
- Die zur Schmierung von Dampfturbinen verwendeten Oele unterliegen dem oxidativen Abbau bei erhöhten Temperaturen, was zur Bildung von Schlamm und zu einem Anstieg des Säuregehalts des Oels führt.
- Versuche zur Lösung dieser Probleme beinhalten die Verwendung einer grossen Anzahl von Korrosionsinhibitoren und Antioxidantien, oder von Mischungen davon, als Schmiermitteladditive.
- So ist aus der US-A 2,856,363 bekannt, dass Zusammensetzungen enthaltend Epoxyalkanamin-Reaktionsprodukte rostinhibierende Eigenschaften besitzen.
- So wurden solche Korrosionsinhibitoren mit gut bekannten phenolischen und/oder aminischen Antioxidantien formuliert. Diese Formulierungen jedoch genügten wohl den korrosionsinhibierenden Anforderungen für Dampfturbinenöle gemäss dem ASTM D-665B-Test, verliehen aber dem Turbinenöl nur ungenügende antioxidative Eigenschaften gemäss dem ASTM D-943-Test.
- Die prioritätsältere, aber nicht vorveröffentlichte EP-A-206998 offenbart Glucamin-Derivate, die u.a. als Stabilisatoren in Schmiermitteln verwendet werden können und die gegenbenenfalls in Kombination mit phenolischen Antioxidantien, aminischen Antioxidantien und Metallpassivatoren eingesetzt werden können.
- Es wurde nun überraschend gefunden, dass die Zusammensetzungen der vorliegenden Erfindung den Anforderungen für Turbinenöle sowohl hinsichtlich korrosionsinhibierender als auch antioxidativer Eigenschaften genügen.
- Demgemäss betrifft die vorliegende Erfindung eine Schmiermittelzusammensetzung mit ausgezeichneten korrosionsinhibierenden und antioxidativen Eigenschaften enthaltend einen überwiegendenden Anteil eines mineralischen Schmieröls und einen geringen Anteil einer Additivzusammensetzung aus
- A) einem Hydroxyalkylalkanolamin-Korrosionsinhibitor,
- B) einem phenolischen Antioxidans,
- C) einem aminischen Antioxidans und
- D) einem Metalldeaktivator vom Azol-Typ,
wobei- (i) eine der Komponenten B) und C) in der Zusammensetzungen fehlen kann und
- ii) die Komponente A) kein Alkanolamin ist, das eine Gruppe
- Eine bevorzugte Gruppe von Hydroxyalkanolamin-Komponenten (A) bilden solche der allgemeinen Formel I,
worin R¹ geradkettiges oder verzweigtes C₈-C₂₀-Alkyl oder einen durch eine bis drei C₁-C₁₂-Alkylgruppen substituierten Phenylrest bedeutet, X = -CH₂-, -O-, -S- oder -C(O)O- ist, R² einen hydroxysubstituierten C₂-C₄-Alkylrest bedeutet, und R³ Wasserstoff ist oder die Bedeutung von R² aufweist, oder Gemische von Verbindungen der Formel I. - Die Verbindungen der Formel I können beispielsweise durch Reaktion einer Verbindung der Formel R¹-XH, worin R¹ und X die vorstehende Bedeutung haben, mit Epichlorhydrin gegebenenfalls in Gegenwart eines Katalysators wie z.B. einer Säure, Base oder Phasentransfer-Katalysators hergestellt werden, wobei eine Verbindung der Formel
entsteht, die anschliessend mit einem Amin der Formel HNR²R³ mit R² und R³ in der vorstehenden Bedeutung umgesetzt wird und so eine Verbindung der Formel I erhalten wird. - Die Komponente (B) ist bevorzugt eine Verbindung der allgemeinen Formel II,
worin R⁴ Wasserstoff oder geradkettiges oder verzweigtes C₁-C₁₂, bevorzugt C₁-C₄, Alkyl bedeutet, oder ist ein Gemisch von Verbindungen der Formel II. - Die Komponente (C) ist bevorzugt eine Verbindung der allgemeinen Formel III
worin R⁵ und R⁶ unabhängig voneinander Wasserstoff, geradkettiges oder verzweigtes C₁-C₁₂-Alkyl, eine Styryl-, Methoxy- oder Isopropoxygruppe bedeuten, oder ist ein Gemisch von Verbindungen der Formel III. - Die Verbindungen der Formeln II und III sind bekannt und nach bekannten Verfahren herstellbar.
- Antioxidans-Gemische von phenolischen und aminischen Typen oder von verschiedenen phenolischen oder verschiedenen aminischen Typen können Verwendung finden, bevorzugt jedoch werden Gemische von phenolischen und aminischen Typen. Besonders bevorzugt werden Gemische von phenolischen und alkylierten Diarylamin-Anitioxidantien, wie z.B. die Produkte, die durch das in der EP-A 149 422 beschriebene Verfahren erhalten werden, insbesondere das Produkt Di-(tert.-octyliertes)-diphenylamin.
- Die Komponente (D) ist bevorzugt eine Verbindung der allgemeinen Formel IV,
worin E Wasserstoff oder einen Rest der Formel -CH₂NR⁷R⁸ bedeutet und R⁷ und R⁸ unabhängig voneinander C₁-C₁₈-Alkyl oder C₂-C₁₈-Alkenyl, darstellen, und welche z.B. durch Reaktion eines 1,2,4-Triazols mit Formaldehyd und einem Amin der Formel HNR⁷R⁸ hergestellt werden können, oder der allgemeinen Formel V,
worin J ein N-Atom oder eine CH₂-Gruppe darstellt, F zusammen mit den C-Atomen, an die F gebunden ist, einen sechsgliedrigen aromatischen oder reduzierten Tetrahydroring bildet, wobei diese Ringe gegebenenfalls alkylsubstituiert sein können, ferner worin G Wasserstoff oder einen Rest der Formel -CH₂NR⁹R¹⁰ bedeutet und R⁹ und R¹⁰ unabhängig voneinander C₁-C₁₈-Alkyl oder C₂-C₁₈-Alkenyl darstellen, und welche z.B. durch Reaktion einer entsprechenden Azolverbindung mit Formaldehyd und einem Amin der Formel HNR⁹R¹⁰ nach der in GB-A 1,061,904, GB-A 1,466,558, GB-A 1,472,527 und GB-A 2,156,813 beschriebenen Weise hergestellt werden können. - Im weiteren kann die Komponente (D) z.B. auch das Reaktionsprodukt eines 1,2,4-Triazols mit einem Zink-bis(0,0'-dialkyldithiophosphat) sein.
- Stellen R⁴ , R⁵, R⁶ oder die Substituenten des Phenylrests R¹ geradkettiges oder verzweigtes C₁-C₁₂-Alkyl dar, so handelt es sich z.B. um Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, sec.-Butyl, Isobutyl, tert.-Butyl, Pentyl, Hexyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl oder Dodecyl.
- Stellen R⁷, R⁸, R⁹ oder R¹⁰ geradkettiges oder verzweiges C₁-C₁₈-Alkyl dar, so handelt es sich z.B. um Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, sec.-Butyl, Isobutyl, tert.-Butyl, Pentyl, Hexyl, Heptyl, Octyl, 2-Ethylhexyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl oder Octadecyl.
- Bevorzugt bedeuten R⁷, R⁸, R⁹ oder R¹⁰ geradkettiges oder verzweigtes C₄-C₁₂-Alkyl.
- Stellen R⁷, R⁸, R⁹ oder R¹⁰ geradkettiges oder verzweigtes C₂-C₁₈-Alkenyl dar, so handelt es sich beispielsweise um Vinyl, Allyl, n-Butenyl, Isopentenyl, Pentenyl, Hexenyl, Heptenyl, Octenyl, Nonenyl, Decenyl, Undecenyl, Dodecenyl, Tridecenyl, Tetradecenyl, Pentadecenyl, Hexadecenyl, Heptadecenyl oder Oleyl.
- Bevorzugt bedeuten R⁷, R⁸, R⁹ oder R¹⁰ C₂-C₆-Alkenyl oder Oleyl.
- Beispiele für spezifische Verbindungen, die als Komponenten für die erfindungsgemässen Schmiermittelzusammensetzungen Verwendung finden, sind:
- N-(2-Hydroxydodecyl)ethanolamin
N-(2-Hydroxydodecyl)diethanolamin
N-(2-Hydroxytetradecyl)ethanolamin
N-(2-Hydroxytetradecyl)diethanolamin
N-(2-Hydroxyhexadecyl)ethanolamin
N-(2-Hydroxyhexadecyl)diethanolamin
N-(2-Hydroxyoctadecyl)ethanolamin
N-(2-Hydroxyoctadecyl)diethanolamin
1-[N,N-Bis(2-hydroxyethyl)amino]-3-octyloxy-propan-2-ol
1-[N,N-Bis(2-hydroxyethyl)amino]-3-isooctyloxy-propan-2-ol
1-[N,N-Bis(2-hydroxyethyl)amino]-3-(tert.-nonylthio)propan-2-ol
1-[N,N-Bis(2-hydroxyethyl)amino]-3-dodecylthio-propan-2-ol
1-[N,N-Bis(2-hydroxyethyl)amino]-3-(tert.-dodecylthio)-propan-2-ol
1-[N,N-Bis(2-hydroxyethyl)amino]-2-hydroxypropyl-3-(tert.-decanoat). - Besonders bevorzugte Verbindungen Der Formel I sind: N-(2-Hydroxydodecyl)diethanolamin
1-[N,N-Bis(2-hydroxyethyl)amino]-3-isooctyloxy-propan-2-ol
1-[N,N-Bis(2-hydroxyethyl)amino]-3-(tert.-nonylthio)propan-2-ol
1-[N,N-Bis(2-hydroxyethyl)amino]-2-hydroxypropyl-3-(tert.-decanoat)
1-[N,N-Bis(2-hydroxyethyl)amino]-3-(4-nonylphenoxy)-propan-2-ol
1-[N,N-Bis(2-hydroxyethyl)amino]-3-(4-tert.-butylphenoxy)-propan-2-ol
1-[N,N-Bis(2-hydroxyethyl)amino]-3-(2,4-diisopropylphenoxy)-propan-2-ol
1-[N,N,-Bis(2-hydroxyethyl)amino]-3-(4-tert.-octylphenoxy)-propan-2-ol oder deren Gemische. - 2,6-Di-tert.-butylphenol
2,6-Di-tert.-butyl-4-methylphenol
2,6-Di-tert.-butyl-4-ethylphenol
2,6-Di-tert.-butyl-4-n-butylphenol
2,6-Di-tert.-butyl-4-isobutylphenol. - Besonders bevorzugte Verbindungen der Formel II sind:
2,6-Di-tert.-butylphenol
2,6-Di-tert.-4-methylphenol oder deren Gemische. - Diphenylamin
Di-(tert.-octyliertes)diphenylamin
Styryl-substituiertes Diphenylamin
4-Isopropoxy-diphenylamin
Di-(4-methoxyphenyl)amin
Gemisch aus mono- und dialkylierten tert.-Butyl-/tert.-Octyldiphenylaminen
oder deren Gemische. - Besonders bevorzugte Verbindungen der Formel III sind:
Di-(tert.-octyliertes)diphenylamin oder ein Gemisch aus mono- und dialkylierten tert.-Butyl-/tert.-Octyldiphenylaminen. - Benztriazol
Tetrahydrobenztriazol
Tolutriazol
Benzimidazol
1,2,4-Triazol
1-[N,N-Bis(2-ethylhexyl)aminomethyl]benztriazol
1-[N,N-Bis(2-ethylhexyl)aminomethyl]tolutriazol
1-[N,N-Bis(2-ethylhexyl)aminomethyl]benzimidazol
1-[N,N-Bis(2-ethylhexyl)aminomethyl]1,2,4-triazol
Produkt der Reaktion von 1,2,4-Triazol mit Zink-bis[0,0ʹ-di-(2-ethylhexyl)dithiophosphat]. - Besonders bevorzugte Verbindungen der Formeln IV und V sind:
1-[N,N-Bis(2-ethylhexyl)aminomethyl]benztriazol
1-[N,N-Bis(2-ethylhexyl)aminomethyl]tolutriazol
1-[N,N-Bis(2-ethylhexyl)aminomethyl]1,2,4-triazol
Produkt der Reaktion von 1,2,4-Triazol mit Zink-bis[0,0ʹ-di-(2-ethylhexyl)dithiophosphat]. - Die Gewichtsverhältnisse der Komponenten (A), (B), (C) und (D) in den erfindungsgemässen Zusammensetzungen können sich je nch Anwendungsart und erforderlichem Grad der Korrosionsinhibierung und antioxidativer Stabilisierung ändern. Im allgemeinen jedoch sind die Verhältnisse bevorzugt wie folgt.
Komponente A: 0.02-0.10 Gew.-%, bevorzugt 0.02-0.05 Gew.-%;
Komponente B: 0.05-0.25 Gew.-%, bevorzugt 0.05-0.15 Gew.-%;
Komponente C: 0.02-0.10 Gew.-%, bevorzugt 0.03-0.06 Gew.-%;
Komponente D: 0.02-0.10 Gew.-%, bevorzugt 0.03-0.06 Gew.-% immer bezogen auf das Gesamtgewicht der Schmiermittelzusammensetzung. - Die Komponenten (A) bis (D) können dem Schmieröl einzeln zugegeben werden. Vorzugsweise werden sie jedoch vorgemischt in Form einer Grundmischung, weiche anschliessend dem Schmieröl zugesetzt wird. Die Grundmischung wird dem Oel in einer genügenden Menge zugesetzt, damit die Anforderungen in Bezug auf den Korrosionsinhibierungsgrad und die antioxidative Stabilisierung erfüllt werden. Die Verwendung der Komponenten in der Form eines vorgemischten Konzentrats ergibt Vorteile bei der Lagerung, dem Transport und der Zugabe zum Oel.
- Demgemäss betrifft die vorliegende Erfindung als weiteren Gegenstand ein korrosionsinhibierendes und antioxidatives Additivkonzentrat enthaltend die Komponenten (A), (B), (C) und (D) mit (A), (B), (C) und (D) in der vorstehenden Bedeutung,
wobei - i) eine der Komponenten B) und C) in der Zusammensetzung fehlen kann und
- ii) die Komponente A) kein Alkanolamin ist, das eine Gruppe
- Das erfindungsgemässe Additivkonzentrat kann nach Belieben mit einem geeigneten inerten Lösungsmittel, wie beispielsweise einem leichten Mineralöl, einem Kerosin oder einem aromatischen Kohlenwasserstoff verdünnt werden. Die Konzentration des Additivkonzentrats wird durch die Löslichkeit der Komponenten (A) bis (D) im Verdünnungsmittel limitiert, jedoch wird im allgemeinen in einem leichten Mineralöl eine Konzentration von 60 Gew.-% an Aktivsubstanzen leicht erreicht.
- Gegenstand der Erfindung ist auch die Verwendung eines erfindungsgemäßen Additivkonzentrats aus (A), (B), (C) und (D) (mit den vorstehenden Maßgaben) zur Korrosionsinhibierung und antioxidativen Stabilisierung von mineralischen Schmierölen.
- Die erfindungsgemässen Schmiermittelzusammensetzungen können zusätzlich zu den Komponenten (A), (B), (C) und (D) noch ein oder mehrere weitere Additive enthalten, die üblicherweise in Schmiermittelzusammensetzungen verwendet werden, um deren Grundeigenschaften weiter zu verbessern, wie z.B. Viskositätsindex-Verbesserer, Stockpunkterniedriger, Dispergiermittel/Tenside oder Hochdruck-/Verschleisschutz-Additive.
- Polymethacrylate, Vinylpyrrolidon/Metacrylat-Copolymere, Polybutene, Olefin-Copolymere, Styrol/Acrylat-Copolymere.
- Polymethacrylat, alkylierte Naphthalinderivate.
- Polybutenylbernsteinsäure-imide, Polybutenylphosphonsäurederivate, basische Magnesium-, Calcium-, und Bariumsulfonate und -phenolate.
- Schwefel und/oder Phosphor und/oder Halogen enthaltende Verbindungen, wie geschwefelte pflanzliche Oele, Zinkdialkyldithiophosphate, Tritolyl-phosphat, chlorierte Paraffine, Alkyl- und Aryldisulfide.
- In den nachfolgenden Beispielen beziehen sich Teile und Prozente auf das Gewicht, sofern nichts anderes angegeben ist.
- Diese Verbindung wird durch Umsetzung von 1,2-Epoxydodecan mit Diethanolamin nach der US Patentschrift 2,856,363 beschriebenen Weise hergestellt.
- 10.5 Teile Diethanolamin werden tropfenweise bei 60°C zu 22.8 Teilen tert.-Nonylcarboxyglycidylether zugegeben. Die so resultierende Lösung wird während 3 Stunden gerührt. Das Rohprodukt wird destilliert und ergibt 28.1 Teile der Verbindung (A4) mit einem Sdp. von 225°C/0,13 mbar.
Elementaranalyse:
Gefunden : C 61.3; H 10.0; N 3.7 %
Berechnet: C 61.6; H 10.5; N 4.2 % - Nach der in Beispiel 2 beschriebenen Weise wird Diethanolamin mit Isooctyloxyglycidylether umgesetzt. Es wird die Verbindung A2 mit einem Sdp. von 190°C/2.34 mbar erhalten.
- Nach der in Beispiel 2 beschriebenen Weise wird Diethanolamin mit tert.-Nonylglycidyl-thioether umgesetzt. Es wird die Verbindung (A3) als gelbe, viskose Flüssigkeit mit einem Berechnungsindex von n
- Nach der in Beispiel 1 der britischen Patentschrift 2,156,813, beschriebenen Weise werden 3.5 Teile 1,2,4-Triazol und 12.05 Teile Di-2-ethylhexylamin mit 100 Teilen Methanol gemischt. Dazu werden 4,05 Teile 36%iges wässriges Formalin zugegeben. Das Gemisch wird während 3 Stunden zum Rückfluss erhitzt. Anschliessend wird das Lösungsmittel unter Wasserstrahl-Vakuum entfernt. So wird die Verbindung (D1) in 100 % Ausbeute mit einem Sdp. von 189°C/0.07 mbar erhalten.
- Ein Gemisch aus 69 Teilen 1,2,4-Triazol und 771 Teilen Zink-bis-[0,0ʹ-di-(2-ethylhexyl)dithiophosphat] wird nach und nach unter Rühren auf 95°C erhitzt. Nach 30 Minuten Rühren bei dieser Temperatur, wird das Produkt eine klare Flüssigkeit. Es wird weiter gerührt bis das Produkt auf Raumtemperatur abgekühlt ist. Das Endprodukt (D2) ist ein klares, gelbes Oel.
- Die Additivzusammensetzungen werden durch Mischen der spezifischen Komponenten in den in Tabelle 1 angegebenen Gewichtsverhältnissen hergestellt.
- Zusammensetzungen der Beispiele 7 bis 17 enthaltend die Komponenten (A) bis (D) werden als Korrosionsinhibitoren in einem Turbinen-Mineralöl mit einer Viskosität von 22 mPa s bei 40°C und 3,8 mPa s Bei 100°C und einem Schwefelgehalt von 0,6 % gemäss dem ASTM D-665B-Test getestet. Die Resultate sind in Tabelle 1 wiedergegeben und geben die Konzentration der Komponenten an, die jeglichen Rostansatz auf der Testspindel verhindern. Die Zusammensetzungen werden auch auf ihre antioxidative Wirkung in einem modifizierten ASTM D-943-Test geprüft. Die Resultate geben die Schlammenge (Oxidationsprodukte) wieder, die sich nach 500 Stunden gebildet haben. Im allgemeinen zeigt eine Oelzusammensetzung mit guten antioxidativen Eigenschaften die Bildung von weniger als 50 mg Schlamm nach der Testdauer.
Claims (18)
- Schmiermittelzusammensetzung mit ausgezeichneten korrosionsinhibierenden und antioxidativen Eigenschaften enthaltend einen überwiegenden Anteil eines mineralischen Schmieröls und einen geringen Anteil einer Additivzusammensetzung ausA) einem Hydroxyalkylalkanolamin-Korrosionsinhibitor,B) einem phenolischen AntioxidansC) einem aminischen Antioxidans undD) einem Metalldeaktivator vom Azol-Typ,
wobei(i) eine der Komponenten B) und C) in der Zusammensetzung fehlen kann und(ii) die Komponente A kein Alkanolamin ist, das eine Gruppe
- Zusammensetzung gemäss Anspruch 1, worin die Hydroxyalkylalkanolamin-Komponente (A) die allgemeine Formel I aufweist,
- Zusammensetzung gemäss Anspruch 1, worin die Komponente (B) eine Verbindung der allgemeinen Formel II ist,
- Zusammensetzung gemäss Anspruch 1, worin die Komponente (C) eine Verbindung der allgemeinen Formel III ist,
- Zusammensetzung gemäss Anspruch 1, worin die Komponente (D) eine Verbindung der allgemeinen Formel IV ist,
- Zusammensetzung gemäss Anspruch 1, worin die Komponente (D) das Reaktionsprodukt eines 1,2,4-Triazols mit einem Zink-bis(0,0ʹ-dialkyldithiophosphat) ist.
- Zusammensetzung gemäss Anspruch 1, worin die Menge an Komponente (A) 0.02-0.10 Gew.-% beträgt.
- Zusammensetzung gemäss Anspruch 1, worin die Menge an Komponente (B) 0.05-0.25 Gew.-% beträgt.
- Zusammensetzung gemäss Anspruch 1, worin die Menge an Komponente (C) 0.02-0.10 Gew.-% beträgt.
- Zusammensetzung gemäss Anspruch 1, worin die Menge an Komponente (D) 0.02-0.10 Gew.-% beträgt.
- Zusammensetzung gemäss Anspruch 2, worin das Hydroxyalkylalkanolamin (A) N-(2-hydroxydodecyl)diethanolamin, 1-[N,N-Bis(-2-hydroxyethyl)amino]-3-isooctyloxy-propan-2-ol, 1-[N,N-Bis(2-hydroxyethyl)amino]-3-(tert.-nonylthio)-propan-2-ol, 1-[N,N-Bis(2-hydroxyethyl)amino]-2-hydroxypropyl-3-(tert.-decanoat), 1-(N,N-Bis-(2-hydroxyethyl)amino]-3-(4-nonylphenoxy)-propan-2-ol, 1-(N,N-Bis-(2-hydroxyethyl)amino]-3-(4-tert.-butylphenoxy)-propan-2-ol,
1-[N,N-Bis(2-hydroxyethyl)amino]-3-(2,4-diisopropylphenoxy)-propan-2-ol oder 1-[N,N-Bis(2-hydroxyethyl)amino]-3-(4-tert.-octylphenoxy)-propan-2-ol oder deren Gemische ist. - Zusammensetzung gemäss Anspruch 3, worin die Komponente (B) 2,6-Di-tert.-butylphenol oder 2,6-di-tert.-butyl-4-methylphenol oder deren Gemische ist.
- Zusammensetzung gemäss Anspruch 4, worin die Komponente (C) Di-(tert.-octyliertes)diphenylamin oder ein Gemisch aus mono- und dialkylierten tert.-Butyl-/tert.-Octyldiphenylaminen ist.
- Zusammensetzung gemäss Anspruch 5, worin die Komponente (D) 1-[N,N-Bis(2-ethylhexyl)aminomethyl]-1,2,4-triazol, 1-[N,N-Bis(2-ethylhexyl)-aminomethyl]-benztriazol, 1-[N,N-Bis(2-ethylhexyl)-aminomethyl]-tolutriazol oder das Reaktionsprodukt von 1,2,4-Triazol mit Zink-bis[0,0ʹ-di-(2-ethylhexyl)dithiophosphat] ist.
- Korrosionsinhibierendes und antioxidatives Additivkonzentrat enthaltend die Komponenten (A), (B) (C) und (D) mit (A), (B), (C) und (D) in der in Anspruch 1 definierten Bedeutung,
wobei(i) eine der Komponenten B) und C) in der Zusammensetzung fehlen kann und(ii) die Komponente A kein Alkanolamin ist, das eine Gruppe
- Additivkonzentrat gemäss Anspruch 15, worin die Komponenten (A) bis (D) mit einem inerten Lösungsmittel verdünnt sind.
- Additivkonzentrat gemäss Anspruch 16, worin das inerte Lösungsmittel ein leichtes Mineralöl, ein Kerosin oder ein aromatischer Kohlenwasserstoff ist.
- Verwendung eines Additivkonzentrats gemäss Anspruch 15 aus (A), (B), (C) und (D) zur Korrosionsinhibierung und antioxidativen Stabilisierung von mineralischen Schmierölen.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868607157A GB8607157D0 (en) | 1986-03-22 | 1986-03-22 | Lubricating compositions |
| GB8607157 | 1986-03-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0239536A2 EP0239536A2 (de) | 1987-09-30 |
| EP0239536A3 EP0239536A3 (en) | 1989-07-26 |
| EP0239536B1 true EP0239536B1 (de) | 1992-06-24 |
Family
ID=10595078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP87810152A Expired - Lifetime EP0239536B1 (de) | 1986-03-22 | 1987-03-16 | Schmiermittelzusammensetzungen |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0239536B1 (de) |
| JP (1) | JPS62270697A (de) |
| CA (1) | CA1284987C (de) |
| DE (1) | DE3779942D1 (de) |
| GB (1) | GB8607157D0 (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01188592A (ja) * | 1988-01-22 | 1989-07-27 | Matsushita Electric Ind Co Ltd | 流体軸受用潤滑油 |
| US5273669A (en) * | 1988-07-18 | 1993-12-28 | Ciba-Geigy Corporation | Lubricant composition |
| US5073278A (en) * | 1988-07-18 | 1991-12-17 | Ciba-Geigy Corporation | Lubricant composition |
| JPH0742468B2 (ja) * | 1989-06-16 | 1995-05-10 | コスモ石油株式会社 | タービン油組成物 |
| EP0432089B1 (de) * | 1989-11-08 | 1996-09-04 | Ciba-Geigy Ag | Schmierstoffzusammensetzungen |
| EP0437416A3 (en) * | 1990-01-11 | 1991-12-18 | Ciba-Geigy Ag | Compositions containing a 2,2',2"-nitrilotriethanol-cyclometallate |
| US5344454A (en) * | 1991-07-24 | 1994-09-06 | Baxter International Inc. | Closed porous chambers for implanting tissue in a host |
| FR2679246A1 (fr) * | 1991-07-15 | 1993-01-22 | Exxon France | Composition d'huile et son utilisation comme isolant electrique. |
| US6773458B1 (en) | 1991-07-24 | 2004-08-10 | Baxter International Inc. | Angiogenic tissue implant systems and methods |
| EP0586194B1 (de) * | 1992-09-02 | 1999-05-06 | The Lubrizol Corporation | Antioxidanten für hoch einfach-ungesättigte pflanzliche Öle |
| US5670464A (en) * | 1993-01-25 | 1997-09-23 | Kao Corporation | Additive for lubricating oils for diesel engines and lubricating oil compositions containing the same |
| KR20080025746A (ko) * | 2005-06-23 | 2008-03-21 | 쉘 인터내셔날 리써취 마트샤피지 비.브이. | 산화 안정성 오일 제형 |
| US20080139421A1 (en) * | 2006-12-06 | 2008-06-12 | Loper John T | Lubricating Composition |
| JP6776495B2 (ja) * | 2015-03-20 | 2020-10-28 | 出光興産株式会社 | 潤滑油組成物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2856363A (en) * | 1955-12-01 | 1958-10-14 | Pure Oil Co | Stable anti-rust lubricating oil |
| US4298481A (en) * | 1979-02-23 | 1981-11-03 | Tenneco Chemicals, Inc. | High temperature grease compositions |
| DE3065464D1 (en) * | 1980-08-12 | 1983-12-08 | Mobil Oil Corp | Lubricant compositions containing antioxidant mixtures of triazoles and thiadiazoles |
| GB2172284B (en) * | 1985-03-12 | 1988-07-27 | Ciba Geigy Ag | Nitrogen-containing additives for non-aqueous functional fluids |
| DE3688011D1 (de) * | 1985-06-21 | 1993-04-22 | Ciba Geigy Ag | Schmiermittelzusammensetzungen, neue glucamin-derivate und diese enthaltende komplexverbindungen. |
-
1986
- 1986-03-22 GB GB868607157A patent/GB8607157D0/en active Pending
-
1987
- 1987-03-16 EP EP87810152A patent/EP0239536B1/de not_active Expired - Lifetime
- 1987-03-16 DE DE8787810152T patent/DE3779942D1/de not_active Expired - Lifetime
- 1987-03-20 JP JP62067733A patent/JPS62270697A/ja active Pending
- 1987-03-20 CA CA000532575A patent/CA1284987C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0239536A3 (en) | 1989-07-26 |
| DE3779942D1 (de) | 1992-07-30 |
| GB8607157D0 (en) | 1986-04-30 |
| JPS62270697A (ja) | 1987-11-25 |
| CA1284987C (en) | 1991-06-18 |
| EP0239536A2 (de) | 1987-09-30 |
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