DD299655A5 - Schmiermittelzusammensetzungen - Google Patents

Schmiermittelzusammensetzungen Download PDF

Info

Publication number: DD299655A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; alkyl; compound; tert; butyl
Prior art date: 1989-05-17

Application number

DD90340726A

Other languages

German (de)

English (en)

Inventor

Robert M O'neil

Hugo Camenzind

Kay St Groeninger

John D Payne

Original Assignee

��`��@��k��

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

1989-05-17

Filing date

1990-05-16

Publication date

1992-04-30

1990-05-16 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1992-04-30 Publication of DD299655A5 publication Critical patent/DD299655A5/de

Links

239000000203 mixture Substances 0.000 title claims abstract description 22
239000000314 lubricant Substances 0.000 title claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 41
-1 amine salts Chemical class 0.000 claims abstract description 35
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
239000010687 lubricating oil Substances 0.000 claims abstract description 14
239000003921 oil Substances 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 34
238000000034 method Methods 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
238000005260 corrosion Methods 0.000 claims description 8
230000007797 corrosion Effects 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 4
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
239000010723 turbine oil Substances 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 claims description 2
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 2
239000010720 hydraulic oil Substances 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000000654 additive Substances 0.000 abstract description 6
230000000996 additive effect Effects 0.000 abstract 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 abstract 1
239000000047 product Substances 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
150000002431 hydrogen Chemical group 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
239000011575 calcium Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000003879 lubricant additive Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
WTWGHNZAQVTLSQ-UHFFFAOYSA-N 4-butyl-2,6-ditert-butylphenol Chemical compound CCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WTWGHNZAQVTLSQ-UHFFFAOYSA-N 0.000 description 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000007866 anti-wear additive Substances 0.000 description 2
229910052788 barium Inorganic materials 0.000 description 2
FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920000193 polymethacrylate Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
231100000241 scar Toxicity 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
WBSRIXCTCFFHEF-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WBSRIXCTCFFHEF-UHFFFAOYSA-N 0.000 description 1
WQXYSVHBMXNXTJ-UHFFFAOYSA-N (3-tert-butyl-4-hydroxyphenyl) butanoate Chemical compound CCCC(=O)OC1=CC=C(O)C(C(C)(C)C)=C1 WQXYSVHBMXNXTJ-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
JUHXTONDLXIGGK-UHFFFAOYSA-N 1-n,4-n-bis(5-methylheptan-3-yl)benzene-1,4-diamine Chemical compound CCC(C)CC(CC)NC1=CC=C(NC(CC)CC(C)CC)C=C1 JUHXTONDLXIGGK-UHFFFAOYSA-N 0.000 description 1
ZJNLYGOUHDJHMG-UHFFFAOYSA-N 1-n,4-n-bis(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(NC(C)CCC(C)C)C=C1 ZJNLYGOUHDJHMG-UHFFFAOYSA-N 0.000 description 1
APTGHASZJUAUCP-UHFFFAOYSA-N 1-n,4-n-di(octan-2-yl)benzene-1,4-diamine Chemical compound CCCCCCC(C)NC1=CC=C(NC(C)CCCCCC)C=C1 APTGHASZJUAUCP-UHFFFAOYSA-N 0.000 description 1
ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 1
XACQZFVINUCPQX-UHFFFAOYSA-N 1-n-phenyl-2-n-propan-2-ylbenzene-1,2-diamine Chemical compound CC(C)NC1=CC=CC=C1NC1=CC=CC=C1 XACQZFVINUCPQX-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
KEXRSLVRFLEMHJ-UHFFFAOYSA-N 1-o,4-o-bis[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl] benzene-1,4-dicarbothioate Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1COC(=S)C1=CC=C(C(=S)OCC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C=C1 KEXRSLVRFLEMHJ-UHFFFAOYSA-N 0.000 description 1
GFVSLJXVNAYUJE-UHFFFAOYSA-N 10-prop-2-enylphenothiazine Chemical compound C1=CC=C2N(CC=C)C3=CC=CC=C3SC2=C1 GFVSLJXVNAYUJE-UHFFFAOYSA-N 0.000 description 1
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
GZZLQUBMUXEOBE-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diol Chemical compound OCCC(C)CC(C)(C)CO GZZLQUBMUXEOBE-UHFFFAOYSA-N 0.000 description 1
XEGAKAFEBOXGPV-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-benzotriazole Chemical compound C1C=CC=C2NNNC12 XEGAKAFEBOXGPV-UHFFFAOYSA-N 0.000 description 1
UUAIOYWXCDLHKT-UHFFFAOYSA-N 2,4,6-tricyclohexylphenol Chemical compound OC1=C(C2CCCCC2)C=C(C2CCCCC2)C=C1C1CCCCC1 UUAIOYWXCDLHKT-UHFFFAOYSA-N 0.000 description 1
ZIVRDIJEVLAWJI-UHFFFAOYSA-N 2,4-dichloro-6-dodecylsulfanyl-1,3,5-triazine Chemical compound CCCCCCCCCCCCSC1=NC(Cl)=NC(Cl)=N1 ZIVRDIJEVLAWJI-UHFFFAOYSA-N 0.000 description 1
QHTMINMDULHUSW-UHFFFAOYSA-N 2,4-dichloro-6-hexadecylsulfanyl-1,3,5-triazine Chemical compound CCCCCCCCCCCCCCCCSC1=NC(Cl)=NC(Cl)=N1 QHTMINMDULHUSW-UHFFFAOYSA-N 0.000 description 1
OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
LXWZXEJDKYWBOW-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(3,5-ditert-butyl-2-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O LXWZXEJDKYWBOW-UHFFFAOYSA-N 0.000 description 1
DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 description 1
CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
JFGVTUJBHHZRAB-UHFFFAOYSA-N 2,6-Di-tert-butyl-1,4-benzenediol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1O JFGVTUJBHHZRAB-UHFFFAOYSA-N 0.000 description 1
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 description 1
FRAQIHUDFAFXHT-UHFFFAOYSA-N 2,6-dicyclopentyl-4-methylphenol Chemical compound OC=1C(C2CCCC2)=CC(C)=CC=1C1CCCC1 FRAQIHUDFAFXHT-UHFFFAOYSA-N 0.000 description 1
SAJFQHPVIYPPEY-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dioctadecoxyphosphorylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SAJFQHPVIYPPEY-UHFFFAOYSA-N 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000007670 refining Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
239000007858 starting material 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
JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical class NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000010689 synthetic lubricating oil Substances 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
235000019303 thiodipropionic acid Nutrition 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008096 xylene Substances 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/38—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
- 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
- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
- 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
- C10N2040/135—Steam engines or turbines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Lubricants (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD90340726A 1989-05-17 1990-05-16 Schmiermittelzusammensetzungen DD299655A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB898911287A GB8911287D0 (en)	1989-05-17	1989-05-17	Lubricant compositions

Publications (1)

Publication Number	Publication Date
DD299655A5 true DD299655A5 (de)	1992-04-30

Family

ID=10656872

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90340726A DD299655A5 (de)	1989-05-17	1990-05-16	Schmiermittelzusammensetzungen

Country Status (7)

Country	Link
US (1)	US5037568A (fr)
EP (1)	EP0398843B1 (fr)
JP (1)	JP2855358B2 (fr)
CA (1)	CA2016837C (fr)
DD (1)	DD299655A5 (fr)
DE (1)	DE69000815T2 (fr)
GB (1)	GB8911287D0 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2128345T3 (es) *	1991-07-17	1999-05-16	Ciba Geigy Ag	Aditivos multifuncionales para lubricantes.
DE4223890A1 (de) *	1992-02-19	1993-08-26	Merck Patent Gmbh	Triazin-derivate
US5420274A (en) *	1993-10-19	1995-05-30	Ciba-Geigy Corporation	Process for the preparation of 2,4-di(alkylamino)-6-alkylthio-s-triazines
JP4548761B2 (ja) *	2000-06-15	2010-09-22	富士フイルムホールディングス株式会社	潤滑剤組成物
DE60210719T2 (de) *	2001-09-25	2007-04-12	Fuji Photo Film Co. Ltd., Minamiashigara	Verbindung enthaltend einen heterozyklischen Ring sowie eine Schmiermittelmischung enthaltend diese
US7485604B2 (en) *	2003-05-27	2009-02-03	Fujifilm Corporation	Lubricant composition and method for using and preparing thereof
GB0416699D0 (en)	2004-07-27	2004-09-01	Prometic Biosciences Ltd	Prion protein ligands and methods of use
BRPI0611811A2 (pt) *	2005-06-10	2008-12-09	Prometic Biosciences Ltd	ligantes de ligaÇço À proteÍna
SG177661A1 (en)	2009-08-04	2012-03-29	Dsm Ip Assets Bv	Coated high strength fibers
CN102933763B (zh)	2010-06-08	2016-02-10	帝斯曼知识产权资产管理有限公司	混杂绳索
WO2011154383A1 (fr)	2010-06-08	2011-12-15	Dsm Ip Assets B.V.	Corde en hmpe protégée
WO2012013659A1 (fr)	2010-07-26	2012-02-02	Dsm Ip Assets B.V.	Câble d'attache pour systèmes d'énergie renouvelable
WO2020128097A1 (fr)	2018-12-21	2020-06-25	Dsm Ip Assets B.V.	Câble pour systèmes aériens de production d'énergie éolienne
EP3899134A1 (fr)	2018-12-21	2021-10-27	Ampyx Power B.V.	Câble pour systèmes de génération d'énergie éolienne en suspension dans l'air
WO2020070342A1 (fr)	2019-01-25	2020-04-09	Dsm Ip Assets B.V.	Système de manille hybride
JP7821725B2 (ja)	2019-11-04	2026-02-27	アビエントプロテクティブマテリアルズビー．ブイ．	ポリマー充填ポリオレフィン繊維

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2836564A (en) *	1954-10-28	1958-05-27	Standard Oil Co	Corrosion inhibitors and compositions containing the same
US3156690A (en) *	1960-04-12	1964-11-10	Geigy Chem Corp	6 (nu-acyl-alkylhydroxyanilino)-2, 4-bis-(alkylthio)-1, 3, 5-triazines
DE1670568A1 (de) *	1967-07-07	1972-02-24	Degussa	Verfahren zur Herstellung von substituierten 2-Mercapto-4,6-dichlor-s-triazinen
GB1224487A (en) *	1968-02-22	1971-03-10	Shell Int Research	Improvements in or relating to ester base compositions
US3819574A (en) *	1970-04-13	1974-06-25	Ciba Geigy Corp	Dialkylphenolthiazines and phenolic antioxidants as stabilizing compositions
US3974162A (en) *	1972-12-21	1976-08-10	American Home Products Corporation	4-Pyrimidinylthioacetic acid derivatives
US4038197A (en) *	1975-10-20	1977-07-26	Standard Oil Company (Indiana)	S-triazine derivatives as multi-functional additives for lubricating oils
IT1211096B (it) *	1981-08-20	1989-09-29	Lpb Ist Farm	Pirimidine e s.triazinici adattivita' ipolipidemizzante.
EP0223916B1 (fr) *	1985-10-03	1991-09-11	ATOCHEM NORTH AMERICA, INC. (a Pennsylvania corp.)	Additifs multifonctionels pour lubrifiants à base de thiadiazole
GB8711191D0 (en) *	1987-05-12	1987-06-17	Bp Chemicals Additives	Lubricating oil additives
GB8728675D0 (en) *	1987-12-08	1988-01-13	Ciba Geigy Ag	Compounds & compositions

1989
- 1989-05-17 GB GB898911287A patent/GB8911287D0/en active Pending
1990
- 1990-05-08 EP EP90810347A patent/EP0398843B1/fr not_active Expired - Lifetime
- 1990-05-08 DE DE9090810347T patent/DE69000815T2/de not_active Expired - Fee Related
- 1990-05-14 US US07/522,630 patent/US5037568A/en not_active Expired - Fee Related
- 1990-05-15 CA CA002016837A patent/CA2016837C/fr not_active Expired - Fee Related
- 1990-05-16 DD DD90340726A patent/DD299655A5/de not_active IP Right Cessation
- 1990-05-17 JP JP2128081A patent/JP2855358B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0398843A1 (fr)	1990-11-22
CA2016837C (fr)	2000-06-20
JP2855358B2 (ja)	1999-02-10
CA2016837A1 (fr)	1990-11-17
US5037568A (en)	1991-08-06
EP0398843B1 (fr)	1993-01-27
DE69000815D1 (de)	1993-03-11
GB8911287D0 (en)	1989-07-05
DE69000815T2 (de)	1993-07-22
JPH0317072A (ja)	1991-01-25

Legal Events

Date	Code	Title	Description
1996-07-18	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0160620B1 (fr)	1989-09-13	Désactivateurs de métaux
EP0376889B1 (fr)	1993-05-19	Composition lubrifiante
DD299655A5 (de)	1992-04-30	Schmiermittelzusammensetzungen
DE68903468T2 (de)	1993-04-15	Schmiermittelzusammensetzungen.
EP0233140A1 (fr)	1987-08-19	Additifs pour lubrifiants contenant du soufre et de l'azote
DE69201592T2 (de)	1995-07-20	Naphthalen-Diamine als Stabilisatoren.
CA1309410C (fr)	1992-10-27	Composition lubrifiante contenant des additifs de lubrification multifonctionnels
EP0125209A2 (fr)	1984-11-14	Compositions lubrifiantes
EP0273868A2 (fr)	1988-07-06	Tétrahydroquinoléines N-substituées comme anti-oxydants pour lubrifiants
EP0205398B1 (fr)	1989-11-08	Additif pour fluides fonctionnels
DE4317980B4 (de)	2007-03-22	Bis-Dithiophosphorsäurederivate als Schmiermitteladditive
EP0524145B1 (fr)	1999-01-27	Additifs multifonctionnels pour lubrifiants
DE69100632T2 (de)	1994-05-11	Carboxyalkylthio-substituierte N,N-Dialkylhydroxylamine und stabilisierte Schmiermittelzusammensetzungen.
US4263157A (en)	1981-04-21	Chlorinated derivatives of butyric acid as useful lubricant additives and lubricants containing same
EP0368803B1 (fr)	1993-04-07	Composition lubrifiante
DE69007214T2 (de)	1994-07-14	Butenylaromatische Aminstabilisatoren.
US4376054A (en)	1983-03-08	1,3,2-Dioxaphospholanes as lubricant additives and lubricants containing same
EP0595771B1 (fr)	1996-11-27	Additifs pour lubrifiants exempts de phosphore
EP0466639B1 (fr)	1994-08-10	Composition de lubrifiant
DE2715529C2 (fr)	1990-05-23
EP0480875B1 (fr)	1994-05-04	Composition de lubrifiant
DE69011597T2 (de)	1994-12-22	Triazol-Derivate.
EP0595770B1 (fr)	1998-01-14	Nouveaux dithiophosphates comme additifs anti-usure
EP0271437B1 (fr)	1990-10-03	Additifs sulfurés pour lubrifiants
DE69001313T2 (de)	1993-09-30	Stabilisiertes organisches Material.