CA1339451C - Composition synthetique fluide, stable a l'oxydation thermique - Google Patents

Composition synthetique fluide, stable a l'oxydation thermique

Info

Publication number: CA1339451C
Authority: CA; Canada
Prior art keywords: carboxylic acid; hydrocarbyl group; ester according; carbon atoms; acid ester
Prior art date: 1988-04-18
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 - Fee Related

Application number

CA000596393A

Other languages

English (en)

Inventor

Richard M. Lange

Mary F. Salomon

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

Lubrizol Corp

Original Assignee

Lubrizol Corp

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

1988-04-18

Filing date

1989-04-12

Publication date

1997-09-09

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22668926&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA1339451(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1989-04-12 Application filed by Lubrizol Corp filed Critical Lubrizol Corp

1997-09-09 Application granted granted Critical

1997-09-09 Publication of CA1339451C publication Critical patent/CA1339451C/fr

2014-09-09 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 58
239000012530 fluid Substances 0.000 title abstract description 20
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 86
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 70
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 43
125000003118 aryl group Chemical group 0.000 claims abstract description 36
150000002009 diols Chemical class 0.000 claims abstract description 14
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
150000002148 esters Chemical class 0.000 claims description 48
239000010687 lubricating oil Substances 0.000 claims description 23
239000000314 lubricant Substances 0.000 claims description 21
239000012141 concentrate Substances 0.000 claims description 11
150000001555 benzenes Chemical class 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
-1 pentaerythritol ester Chemical class 0.000 description 38
239000003921 oil Substances 0.000 description 22
150000001298 alcohols Chemical class 0.000 description 21
239000000047 product Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 16
125000001931 aliphatic group Chemical group 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 8
239000000654 additive Substances 0.000 description 8
239000002270 dispersing agent Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
238000000034 method Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
CWPPDTVYIJETDF-UHFFFAOYSA-N 2,2,4-trimethylpentan-1-ol Chemical compound CC(C)CC(C)(C)CO CWPPDTVYIJETDF-UHFFFAOYSA-N 0.000 description 7
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 7
239000000920 calcium hydroxide Substances 0.000 description 7
229910001861 calcium hydroxide Inorganic materials 0.000 description 7
238000010992 reflux Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
239000002585 base Substances 0.000 description 6
229910001651 emery Inorganic materials 0.000 description 6
238000005886 esterification reaction Methods 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
238000010533 azeotropic distillation Methods 0.000 description 5
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
230000001050 lubricating effect Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
239000003039 volatile agent Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
239000005909 Kieselgur Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
230000000996 additive effect Effects 0.000 description 4
150000001447 alkali salts Chemical class 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000002518 antifoaming agent Substances 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
230000008569 process Effects 0.000 description 4
238000010926 purge Methods 0.000 description 4
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
239000010689 synthetic lubricating oil Substances 0.000 description 4
229940087291 tridecyl alcohol Drugs 0.000 description 4
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003599 detergent Substances 0.000 description 3
GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 3
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000032050 esterification Effects 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
150000003077 polyols Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 3
238000002411 thermogravimetry Methods 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 2
DPQMSIBAADLGOH-UHFFFAOYSA-N 2,2,3-trimethylheptan-1-ol Chemical compound CCCCC(C)C(C)(C)CO DPQMSIBAADLGOH-UHFFFAOYSA-N 0.000 description 2
KEXGXAGJHHCTKD-UHFFFAOYSA-N 2,2-dimethyl-1-Octanol Chemical compound CCCCCCC(C)(C)CO KEXGXAGJHHCTKD-UHFFFAOYSA-N 0.000 description 2
VZCOFGHOKLEMPL-UHFFFAOYSA-N 2-ethyl-2-methylpentan-1-ol Chemical compound CCCC(C)(CC)CO VZCOFGHOKLEMPL-UHFFFAOYSA-N 0.000 description 2
UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
238000002485 combustion reaction Methods 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
238000000113 differential scanning calorimetry Methods 0.000 description 2
VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 2
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
230000006872 improvement Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
239000000178 monomer Substances 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 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
150000002989 phenols Chemical class 0.000 description 2
150000003017 phosphorus Chemical class 0.000 description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
229920001281 polyalkylene Polymers 0.000 description 2
229920013639 polyalphaolefin Polymers 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
229920001748 polybutylene Polymers 0.000 description 2
229920006389 polyphenyl polymer Polymers 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
150000003138 primary alcohols Chemical class 0.000 description 2
RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
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 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
235000011044 succinic acid Nutrition 0.000 description 2
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
NNYHMCFMPHPHOQ-UHFFFAOYSA-N mellitic anhydride Chemical compound O=C1OC(=O)C2=C1C(C(OC1=O)=O)=C1C1=C2C(=O)OC1=O NNYHMCFMPHPHOQ-UHFFFAOYSA-N 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
229940073769 methyl oleate Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
BTHGHFBUGBTINV-UHFFFAOYSA-N naphthalene-2,3,6-tricarboxylic acid Chemical compound C1=C(C(O)=O)C(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 BTHGHFBUGBTINV-UHFFFAOYSA-N 0.000 description 1
KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000005325 percolation Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
239000001739 pinus spp. Substances 0.000 description 1
229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
239000003079 shale oil Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
230000008961 swelling Effects 0.000 description 1
230000002522 swelling effect Effects 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
150000001911 terphenyls Chemical class 0.000 description 1
229920001897 terpolymer Polymers 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
MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
PQRRMYYPKMKSNF-UHFFFAOYSA-N tris(4-methylpentan-2-yl) tris(4-methylpentan-2-yloxy)silyl silicate Chemical compound CC(C)CC(C)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)OC(C)CC(C)C PQRRMYYPKMKSNF-UHFFFAOYSA-N 0.000 description 1
QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
229940036248 turpentine Drugs 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
USEBTXRETYRZKO-UHFFFAOYSA-L zinc;n,n-dioctylcarbamodithioate Chemical compound [Zn+2].CCCCCCCCN(C([S-])=S)CCCCCCCC.CCCCCCCCN(C([S-])=S)CCCCCCCC USEBTXRETYRZKO-UHFFFAOYSA-L 0.000 description 1
239000004711 α-olefin 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
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/008—Lubricant compositions compatible with refrigerants
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/36—Esters of polycarboxylic acids
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M129/68—Esters
- C10M129/72—Esters of polycarboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Emergency Medicine (AREA)
Health & Medical Sciences (AREA)
Lubricants (AREA)
Compositions Of Macromolecular Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)

CA000596393A 1988-04-18 1989-04-12 Composition synthetique fluide, stable a l'oxydation thermique Expired - Fee Related CA1339451C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US18254488A	1988-04-18	1988-04-18
US182,544		1988-04-18

Publications (1)

Publication Number	Publication Date
CA1339451C true CA1339451C (fr)	1997-09-09

Family

ID=22668926

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000596393A Expired - Fee Related CA1339451C (fr)	1988-04-18	1989-04-12	Composition synthetique fluide, stable a l'oxydation thermique

Country Status (10)

Country	Link
EP (1)	EP0376997B2 (fr)
JP (1)	JP2991732B2 (fr)
AT (1)	ATE117288T1 (fr)
AU (1)	AU616010B2 (fr)
CA (1)	CA1339451C (fr)
DE (1)	DE68920723T3 (fr)
IL (1)	IL89909A (fr)
MX (1)	MX173426B (fr)
WO (1)	WO1989010345A1 (fr)
ZA (1)	ZA892794B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5798319A (en) *	1996-01-16	1998-08-25	Exxon Chemical Patents Inc.	High stability and low metals esters based on 3,5,5-trimethyl-1-hexanol

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1200141A (fr) *	1957-01-08	1959-12-18	American Cyanamid Co	Nouveaux plastifiants pour résines vinyliques constitués par des esters dialiphatiques d'un acide dicarboxylique, et compositions de résines contenant ces plastifiants
NL230545A (fr) *	1957-08-21
NL234783A (fr) *	1958-01-02
US3329643A (en)	1965-11-15	1967-07-04	Eastman Kodak Co	Polymeric compositions plasticized with 2, 2-dimethylalkyl esters of dibasic acids
US3624133A (en) *	1966-04-22	1971-11-30	Robert H Reitsema	Liquid esters of naphthalene dicarboxylic acids
US3637501A (en) *	1968-11-05	1972-01-25	Ethyl Corp	Complex esters
US3740625A (en)	1971-11-04	1973-06-19	Sprague Electric Co	Electrical capacitors with ester impregnants
JPS5224626B2 (fr) *	1973-03-14	1977-07-02
JPS5230274B2 (fr) *	1973-12-19	1977-08-06
JPS5940489B2 (ja) *	1977-08-19	1984-10-01	東レ株式会社	ガス遠心分離機
GB8408017D0 (en) *	1984-03-28	1984-05-10	Bp Chem Int Ltd	Oil-based lubricant compositions

1989
- 1989-04-07 EP EP89904950A patent/EP0376997B2/fr not_active Expired - Lifetime
- 1989-04-07 JP JP1504772A patent/JP2991732B2/ja not_active Expired - Lifetime
- 1989-04-07 AU AU34453/89A patent/AU616010B2/en not_active Ceased
- 1989-04-07 AT AT89904950T patent/ATE117288T1/de active
- 1989-04-07 DE DE68920723T patent/DE68920723T3/de not_active Expired - Fee Related
- 1989-04-07 WO PCT/US1989/001454 patent/WO1989010345A1/fr not_active Ceased
- 1989-04-11 IL IL89909A patent/IL89909A/xx not_active IP Right Cessation
- 1989-04-12 CA CA000596393A patent/CA1339451C/fr not_active Expired - Fee Related
- 1989-04-17 ZA ZA892794A patent/ZA892794B/xx unknown
- 1989-04-17 MX MX015680A patent/MX173426B/es unknown

Also Published As

Publication number	Publication date
WO1989010345A1 (fr)	1989-11-02
EP0376997B1 (fr)	1995-01-18
AU616010B2 (en)	1991-10-17
JP2991732B2 (ja)	1999-12-20
EP0376997B2 (fr)	1999-03-31
JPH03502588A (ja)	1991-06-13
EP0376997A1 (fr)	1990-07-11
ATE117288T1 (de)	1995-02-15
MX173426B (es)	1994-03-03
AU3445389A (en)	1989-11-24
IL89909A0 (en)	1989-12-15
DE68920723T3 (de)	1999-07-22
ZA892794B (en)	1989-12-27
DE68920723D1 (en)	1995-03-02
DE68920723T2 (de)	1995-05-18
IL89909A (en)	1993-02-21

Legal Events

Date	Code	Title	Description
2003-09-09	MKLA	Lapsed

Publication	Publication Date	Title
US4479883A (en)	1984-10-30	Lubricant composition with improved friction reducing properties containing a mixture of dithiocarbamates
US5942475A (en)	1999-08-24	Engine oil lubricants formed from complex alcohol esters
EP0149549B1 (fr)	1992-06-24	Sels de cuivre de dérivés d'anhydride succinique
US4234497A (en)	1980-11-18	Iso-palmitate polyol ester lubricants
US4376711A (en)	1983-03-15	Lubricant composition
CN1093851C (zh)	2002-11-06	基于3,5,5－三甲基－1－己醇的高稳定性和低金属含量的酯
EP0131400A2 (fr)	1985-01-16	Sels métalliques d'acides d'alkylphosphorodithioiques inférieurs
JP2001207185A (ja)	2001-07-31	潤滑油組成物
EP0925339A1 (fr)	1999-06-30	Esters d'alcool complexes a viscosite elevee
CA2350768A1 (fr)	2000-05-25	Compositions et composes complexes solubles d'ester d'alcool
US5750750A (en)	1998-05-12	High viscosity complex alcohol esters
JP2834753B2 (ja)	1998-12-14	ポリコハク酸エステルおよびそれらを含有する潤滑組成物
US5674822A (en)	1997-10-07	Synthetic ester base stocks for low emission lubricants
US4769164A (en)	1988-09-06	Anti-oxidant products
KR100706479B1 (ko)	2007-04-10	칼사이트를 함유한 과염기 세제를 포함하는 오일 분산물을정화하는 방법
US4803004A (en)	1989-02-07	Reaction products of alkenylsuccinic compounds with aromatic amines and hindered alcohols and lubricant compositions thereof
US5164122A (en)	1992-11-17	Thermal oxidatively stable synthetic fluid composition
US4551257A (en)	1985-11-05	Amides from dialkylenetriamines and lubricant and fuel compositions containing same
AU616010B2 (en)	1991-10-17	Thermal oxidatively stable synthetic fluid composition
US5037569A (en)	1991-08-06	Anti-oxidant products
US4895579A (en)	1990-01-23	Reaction products of alkenylsuccinic compounds with aromatic amines and hindered alcohols and lubricant and fuel compositions thereof
US5254276A (en)	1993-10-19	Diol phosphite adducts of olefins as multifunctional lubricants and additives for lubricants
US12091628B2 (en)	2024-09-17	Estolide composition and process for making estolides
JPH11152485A (ja)	1999-06-08	ガスエンジン油
JP2001514241A (ja)	2001-09-11	２−アルキルアルカン−１−オールを有する芳香族ポリカルボン酸のエステル