NO772682L - LIQUID ANTIOXIDANT WITH IMPROVED SOLUBILITY IN LUBRICANT OILS - Google Patents
LIQUID ANTIOXIDANT WITH IMPROVED SOLUBILITY IN LUBRICANT OILSInfo
- Publication number
- NO772682L NO772682L NO772682A NO772682A NO772682L NO 772682 L NO772682 L NO 772682L NO 772682 A NO772682 A NO 772682A NO 772682 A NO772682 A NO 772682A NO 772682 L NO772682 L NO 772682L
- Authority
- NO
- Norway
- Prior art keywords
- liquid
- mixture according
- parts
- mixture
- lubricant
- Prior art date
Links
- 239000007788 liquid Substances 0.000 title claims description 29
- 239000000314 lubricant Substances 0.000 title claims description 11
- 230000003078 antioxidant effect Effects 0.000 title claims description 8
- 239000003963 antioxidant agent Substances 0.000 title claims description 5
- 239000003921 oil Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 52
- 239000000047 product Substances 0.000 claims description 14
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 10
- 239000013638 trimer Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000010687 lubricating oil Substances 0.000 claims description 6
- UQJDVLPHTXQTRP-UHFFFAOYSA-N 2,2-bis(heptanoyloxymethyl)butyl heptanoate Chemical group CCCCCCC(=O)OCC(CC)(COC(=O)CCCCCC)COC(=O)CCCCCC UQJDVLPHTXQTRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical group FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- VFQLXEJMJXFMLY-UHFFFAOYSA-N 1-phenylnaphthalen-2-amine Chemical group NC1=CC=C2C=CC=CC2=C1C1=CC=CC=C1 VFQLXEJMJXFMLY-UHFFFAOYSA-N 0.000 claims 1
- 239000010688 mineral lubricating oil Substances 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 5
- -1 synthetic Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 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 2
- 239000002245 particle Substances 0.000 description 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- KDMAJIXYCNOVJB-UHFFFAOYSA-N 2,2-bis(nonanoyloxymethyl)butyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCCC)COC(=O)CCCCCCCC KDMAJIXYCNOVJB-UHFFFAOYSA-N 0.000 description 1
- HFWHTGSLDKKCMD-UHFFFAOYSA-N 2,2-bis(octanoyloxymethyl)butyl octanoate Chemical compound CCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC HFWHTGSLDKKCMD-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- BBCLXYJRPRRZQW-UHFFFAOYSA-N 2-phenylnaphthalen-1-amine Chemical compound C1=CC2=CC=CC=C2C(N)=C1C1=CC=CC=C1 BBCLXYJRPRRZQW-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- WIYAGHSNPUBKDT-UHFFFAOYSA-N dinonyl hexanedioate Chemical compound CCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCC WIYAGHSNPUBKDT-UHFFFAOYSA-N 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical group CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino 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
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
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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
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Description
Foreliggende oppfinnelse vedrører nye, væskeformige blandinger for anvendelse som antioksydasjonsmidler i mineraloljer, syntetiske, væskeformige hydrocarboner og syntetiske, væskeformige estere.. De aktuelle forbindelsene er p-alkylf enylderivat av a- og" (3-naf tylamin. The present invention relates to new, liquid mixtures for use as antioxidants in mineral oils, synthetic, liquid hydrocarbons and synthetic, liquid esters. The relevant compounds are p-alkylphenyl derivatives of α- and "(3-naphthylamine.
For at en forbindelse skal kunne anvendes som anti-oksydas jonsmiddel i væskeformige smøremidler, bør den være blandbar med og oppløselig i slike smøremidler ved normale temperaturer, dette for å lette oppløsningen og spare tid og energi. In order for a compound to be used as an anti-oxidation agent in liquid lubricants, it should be miscible with and soluble in such lubricants at normal temperatures, this to facilitate dissolution and save time and energy.
Produktene ifølge foreliggende oppfinnelse er væskerThe products according to the present invention are liquids
som lett kan blandes med og oppløses direkte i oljen i pas-sende mengder uten at det er nødvendig med oppvarming. -Dette medfører ønsket innsparing av tid og energi. En annen fordel med slike væskeformige blandinger er i sammenligning med krystallinske blandinger, at væsker er lettere å håndtere. Således kan væsker lett lagres og pumpes inn i sluttproduktet which can be easily mixed with and dissolved directly in the oil in suitable quantities without the need for heating. - This results in the desired saving of time and energy. Another advantage of such liquid mixtures is, in comparison with crystalline mixtures, that liquids are easier to handle. Thus, liquids can be easily stored and pumped into the final product
i riktige mengder. Disse riktige mengder kan bestemmes enten ved veiing eller, mer hensiktsmessig, volumetrisk. in the right quantities. These correct amounts can be determined either by weighing or, more conveniently, volumetrically.
Skjønt det normalt ikke er nødvendig, kan man, om ønsket, fremstille konsentrater av disse væskeformige blandinger for tilsetning til oljen og dette kan lett oppnås ettersom disse produkter er blandbare og oppløselige (til og med ved lave temperaturer) i alle mengdeforhold i både væskeformige hydrocarboner og væskeformige estere. Således fremstilles lett 50$>ige oppløsninger ved enkel sammenblanding ved romtemperatur. Opp-løsningene forblir homogene tii og med ved meget lave temperaturer . Although not normally necessary, if desired, concentrates of these liquid mixtures can be prepared for addition to the oil and this can be easily achieved as these products are miscible and soluble (even at low temperatures) in all proportions in both liquid hydrocarbons and liquid esters. Thus, 50% solutions are easily prepared by simple mixing at room temperature. The solutions remain homogeneous even at very low temperatures.
Blant typiske oljer som kan beskyttes med antioksyda-sjonsmidlene ifølge foreliggende oppfinnelse, kan følgende nev-ne s : Among typical oils that can be protected with the antioxidants according to the present invention, the following can be mentioned:
1. Alle mineraloljer1. All mineral oils
2. Syntetiske hydrocarbonoljer fremstilt ved polymeri-sasjon av 1-olefiner, slik som hexen-1, okten-1, decen-1, dodecen-1 og isobuten. 3. Væskeformige, syntetiske estere basert,;på en eller flere organiske carboxylsyreestere beregnet for anvendelse ved temperaturer på 200°C og høyere. Eksempler på slike syntetiske smøremidler er smøremidler basert på en diester av en tobasisk syre og en en-verdig alkohol, eksempelvis dioktylsebacat eller dinonyladipat; på en triester av trimetylolpropan og en enbasisk syre eller en blanding av enbasiske syrer, eksempelvis trimetylolpropan-tripelargonat eller trimetylolpropan- trikaprilat ; på en tetraester av penta-erytritol og en en basisk syre eller en blanding av 2. Synthetic hydrocarbon oils produced by polymerisation of 1-olefins, such as hexene-1, octene-1, decene-1, dodecene-1 and isobutene. 3. Liquid, synthetic esters based on one or more organic carboxylic acid esters intended for use at temperatures of 200°C and higher. Examples of such synthetic lubricants are lubricants based on a diester of a dibasic acid and a monohydric alcohol, for example dioctyl sebacate or dinonyl adipate; on a triester of trimethylolpropane and a monobasic acid or a mixture of monobasic acids, for example trimethylolpropane tripelargonate or trimethylolpropane tricaprylate; on a tetraester of penta-erythritol and a basic acid or a mixture of
enbasiske syrer, eksempelvis pentaerytritoltetrakapri-lan eller på kompliserte estere også baserte på enbasiske syrer, tobasiske syrer og flerverdige alkoholer eller på blandinger derav. monobasic acids, for example pentaerythritoltetracaprylan or on complicated esters also based on monobasic acids, dibasic acids and polyhydric alcohols or on mixtures thereof.
De formler som eksemplifiserer de aktuelle strukturerThe formulas that exemplify the relevant structures
i foreliggende oppfinnelse er følgende: in the present invention are the following:
hvor R er blandede propylentrimerer. where R is mixed propylene trimers.
Disse forbindelser kan fremstilles ved at man utsetter enten a- eller |3-fenylnaftylamin for innvirkning av en blanding av propylentrimerer og en Friedel-Crafts-katalysator, f.eks. aluminiumklorid, bortrifluorid eller lignende. Reaksjonen kan gjennomføres ved en temperatur mellom normal romtemperatur og 300°C. Det er foretrukket å gjennomføre reaksjonen i inert atmosfære, men dette er ikke nødvendig. Ved fremgangsmåten ifølgeroppfinnelsen inneholder reaksjonsproduktene et alkyle-ringsmiddel som omfatter flere (dvs. minst 30) isomerer, hvilke er trimerer av propen. Typiske slike forbindelser har følgende strukturformler: These compounds can be prepared by exposing either α- or β-phenylnaphthylamine to the action of a mixture of propylene trimers and a Friedel-Crafts catalyst, e.g. aluminum chloride, boron trifluoride or the like. The reaction can be carried out at a temperature between normal room temperature and 300°C. It is preferred to carry out the reaction in an inert atmosphere, but this is not necessary. In the method according to the invention, the reaction products contain an alkylating agent which comprises several (ie at least 30) isomers, which are trimers of propene. Typical such compounds have the following structural formulas:
og lignende. and such.
Selv ora det er mulig at ikke alle olefinene i en slik blanding kan alkylere fenylnaftylamin.er på den ovenfor angitte måte, foreligger dog et flertall olefiner i en slik blanding som kan gi alkyleringsprodukter. Bevis for at de resulterende, alkylerte fenylnaftylaminene er blandinger av forskjellige isomerer, angis i den nedenfor detaljerte beskrivelse av teg-ningene . Although it is possible that not all of the olefins in such a mixture can alkylate phenylnaphthylamine in the manner indicated above, there are however a majority of olefins in such a mixture which can give alkylation products. Evidence that the resulting alkylated phenylnaphthylamines are mixtures of different isomers is given in the detailed description of the drawings below.
Det faktum at reaksjonsproduktet er en blanding av isomere forbindelser (i motsetning til de rene, enkle forbindelsene som er beskrevet i litteraturen) og de innførte alkyl-gruppenes asymmetri, kan forhindre den krystallisasjon av produktet som ville opptre ved anvendelse av en ren, mer symmetrisk forbindelse. The fact that the reaction product is a mixture of isomeric compounds (as opposed to the pure, simple compounds described in the literature) and the asymmetry of the introduced alkyl groups can prevent the crystallization of the product that would occur using a pure, more symmetrical connection.
I figurene IA og IB vises gassfasekromatogram av de blandede propylentrimerene (nonenblanding) som anvendes ifølge foreliggende oppfinnelse. Figures IA and IB show gas phase chromatograms of the mixed propylene trimers (nonene mixture) used according to the present invention.
I figur 2 vises et væskekromatogram av en destillert Figure 2 shows a liquid chromatogram of a distilled
nony1fenyl-a-Naftylamin.nony1phenyl-a-Naphthylamine.
Hver topp i figurene IA og IB tilsvarer en enkelt isomer og det totale areal under hver topp står i direkte forhold til mengden av aktuell isomer i blandingen. Each peak in Figures IA and IB corresponds to a single isomer and the total area under each peak is directly proportional to the amount of the relevant isomer in the mixture.
Figurene IA og IB er basert på en kurve oppnådd ved vurdering av en prøve i en gasskromatograf (Perkin Eimer 226) med en kolonne (lengde 90 m og diameter 3 mm) belagt med 95$> skva-len og 5$ av et tensid (ATPET-80). Temperaturen i kolonnen var 75°C. En mikroliter av prøven ble innført i apparatets injek-sjonsblokk som ble holdt ved 90°C. Følgende gasser ble benyttet med de angitte trykk: H2, 83 kPa; luft, 33^ kPa; He, 276 kPa. Figures IA and IB are based on a curve obtained by evaluating a sample in a gas chromatograph (Perkin Eimer 226) with a column (length 90 m and diameter 3 mm) coated with 95% of squalene and 5% of a surfactant ( ATPET-80). The temperature in the column was 75°C. One microliter of the sample was introduced into the injection block of the apparatus which was maintained at 90°C. The following gases were used at the indicated pressures: H2, 83 kPa; air, 33^ kPa; Huh, 276 kPa.
I fig. 2 vises et diagram oppnådd ved vurdering av prø-ver i en væskekromatograf (DuPong 830) med en kolonne ("ZORBAX ODS") med lengde 25 cm og indre diameter k, 6 mm. Kolonnen var pakket med et materiale fremstilt ved kjemisk binding av oktadecylsilangrupper til partikler av "ZORBAX SIL". De således oppnådde bundne partikler var sfæriske og hadde diameter 6-8 um. In fig. 2 shows a diagram obtained by evaluating samples in a liquid chromatograph (DuPong 830) with a column ("ZORBAX ODS") of length 25 cm and inner diameter k, 6 mm. The column was packed with a material produced by chemically bonding octadecylsilane groups to particles of "ZORBAX SIL". The bound particles thus obtained were spherical and had a diameter of 6-8 µm.
I alle figurene skal kurvene leses fra høyre (der den første toppen opptrådte) mot venstre (der den siste toppen ble dannet). In all the figures, the curves should be read from the right (where the first peak appeared) to the left (where the last peak formed).
Som påpekt ovenfor fremstilles de alkylerte fenylnaftylaminene ved omsetning av et alken (R) med fenylnaftylamin og reaksjonen katalyseres med en Friedel-Crafts-katalysator, eksempelvis A1C1 eller BF^. As pointed out above, the alkylated phenylnaphthylamines are produced by reacting an alkene (R) with phenylnaphthylamine and the reaction is catalyzed with a Friedel-Crafts catalyst, for example AlCl or BF^.
Hvis R er en eneste, enkelt forbindelse, da,nnes et eneste, enkelt alkylert produkt. Like åpenbart er det at det dannes en blanding av alkylerte produkter dersom R er en blanding av forbindelser. If R is a single, single compound, then a single, single alkylated product is obtained. It is equally obvious that a mixture of alkylated products is formed if R is a mixture of compounds.
I foreliggende tilfelle kan bare den førstnevnte iso-meren gi kjemisk alkylering av fenyl-a-naftylaminet og det alkylerte produkt har følgelig nedenstående struktur: In the present case, only the first-mentioned isomer can give chemical alkylation of the phenyl-α-naphthylamine and the alkylated product consequently has the following structure:
Det faktum at dette er en eneste forbindelse frem- The fact that this is a single connection forward-
går av dens skarpe smeltepunkt ( j6- 77°C). En blanding av forbindelser ville smelte innen et bredere intervall. goes by its sharp melting point (j6- 77°C). A mixture of compounds would melt within a wider interval.
Nevnte faktum bevises også av at det i fig. 3 bare forekommer en eneste, meget smal topp.. Said fact is also proven by the fact that in fig. 3 only a single, very narrow peak occurs..
I motsetning til dette er det alkylerte produkt ifølge foreliggende oppfinnelse et resultat av en reaksjon av en blanding av alkener (r) slik at det alkylerte produkt nødven-digvis er en blanding av forbindelser. De i figurene IA og IB angitte kromatogrammer angår de blandede propylentrimerene som anvendes ved alkyleringen av fenylnaftylaminen ifølge foreliggende oppfinnelse. Det fremgår klart at det finnes over 30 hovedisomerer i blandingen. Ingen enkelt isomer utgjør selv 10% av den totale blanding. Det bemerkes at det i nedenstående eksempel anvendes et dobbelt molart overskudd av den blandede trimeren fordi noen av bestanddelene i blandingen er a<y>en type som ikke alkylerer fenylnaftylaminene. Siden man, slik det fremgår av en analyse av reaksjonsproduktet, oppnår vesentlig kvantitativt utbytte av monoalkyleringsprodukt, er det statistisk nødvendig at det dannes flere alkylerte produkter. Det er utvilsomt riktig at hovedmaksimum i fig. 2 i realiteten er en blanding av isomerer. På grunn av at forbindelsene er ekstremt like hverandre, har man ikke kunnet oppnå god oppløs-ning, men en sammenligning mellom figurene 2 og 3 viser at bredden på hovedtoppen i fig. 2 er 2-3 ganger så stor som høy-den til hovedtoppen i fig. 3, og dette viser at det i materia-let ifølge fig. 2 forekommer flere isomerer. Omtrent 6 isomer-komponenter som forekommer i mindre mengder skiller seg til-strekkelig fra hovedkomponentene for å gi særskilte topper ved den benyttede kromatografiske metode. Dette for at reaksjonsproduktet ifølge foreliggende oppfinnelse er en isomerblanding, er at produktet er væskeformig, det ovenfor antydede statis- tiske faktum og kurven i fig. 3. In contrast, the alkylated product according to the present invention is the result of a reaction of a mixture of alkenes (r) so that the alkylated product is necessarily a mixture of compounds. The chromatograms shown in Figures IA and IB relate to the mixed propylene trimers used in the alkylation of the phenylnaphthylamine according to the present invention. It is clear that there are over 30 main isomers in the mixture. No single isomer makes up even 10% of the total mixture. It is noted that in the example below a double molar excess of the mixed trimer is used because some of the components in the mixture are of a type that do not alkylate the phenylnaphthylamines. Since, as can be seen from an analysis of the reaction product, a significant quantitative yield of monoalkylation product is obtained, it is statistically necessary that more alkylated products are formed. It is undoubtedly true that the main maximum in fig. 2 in reality is a mixture of isomers. Due to the fact that the connections are extremely similar to each other, it has not been possible to achieve good resolution, but a comparison between figures 2 and 3 shows that the width of the main peak in fig. 2 is 2-3 times as large as the height of the main peak in fig. 3, and this shows that in the material according to fig. 2 several isomers occur. Approximately 6 isomeric components occurring in smaller amounts differ sufficiently from the main components to give distinct peaks by the chromatographic method used. This is because the reaction product according to the present invention is a mixture of isomers, that the product is liquid, the statistical fact indicated above and the curve in fig. 3.
Generelt tilsettes 0,05-^, fortrinnsvis 0,2-2,5 deler av de alkylerte fenylnaftylaminene ifølge oppfinnelsen til 100 deler av den for stabilisering beregnede smøreolje. In general, 0.05-2, preferably 0.2-2.5 parts of the alkylated phenylnaphthylamines according to the invention are added to 100 parts of the lubricating oil intended for stabilization.
I følgende eksempler belyses fremstillingen av forbindelsene ifølge oppfinnelsen. The following examples illustrate the preparation of the compounds according to the invention.
Eksempel 1Example 1
109,5 g (0,5 mol) fenyl-a-naftylamin og 126 g (l mol) blandede propylentrimerer, ble sammenblandet i en rundkolbe med tre halser og forsynt med rører, tilbakeløpskondensator og termometer. Et statisk overtrykk av nitrogen ble opprettholdt via kondensatorens øvre ende. Til ovennevnte blanding ble det tilsatt 1,5 S AlCl^og det hele oppvarmet til 120°C og denne 109.5 g (0.5 mol) of phenyl-α-naphthylamine and 126 g (1 mol) of mixed propylene trimers were mixed in a three-necked round bottom flask fitted with a stirrer, reflux condenser and thermometer. A static overpressure of nitrogen was maintained via the condenser's upper end. To the above mixture was added 1.5 S AlCl^ and the whole heated to 120°C and this
temperatur ble holdt i 2k timer. Deretter fikk reaksjonsblan-dingen avkjøles til romtemperatur og 30 ml hexan ble tilsatt. -Den således oppnådde oppløsning ble filtrert for å fjerne spormengder av uoppløselig katalysator og ble deretter vasket med en 5%ig oppløsning av NaOH (2x300 ml). Hexanoppløsningen ble vasket med vann til nøytralitet. Oppløsningen ble tørket med MgSO^som deretter ble frafiltrert. Hexanen og propylen-trimeroverskuddet ble avdestillert ved atmosfæretrykk. Til slutt ble det nådd en temperatur på 250°C i destillasjonskol-ben og på dette tidspunkt ble det opprettet et undertrykk på 20 mm for å sikre fullstendig fjerning av propylentrimerover-skuddet. Resten i kolben veide 165 g. Det teoretiske utbytte for fullstendig monoalkylering er 172 gram. Resten besto av en sirup som ikke krystalliserte, hverken i ublandet tilstand eller fra en hexanoppløsning ( lOtfo) ved -78°C. Denne rest hadde følgende analyse: temperature was maintained for 2k hours. The reaction mixture was then allowed to cool to room temperature and 30 ml of hexane was added. - The solution thus obtained was filtered to remove trace amounts of insoluble catalyst and was then washed with a 5% solution of NaOH (2x300 ml). The hexane solution was washed with water to neutrality. The solution was dried with MgSO 4 , which was then filtered off. The hexane and the propylene trimer excess were distilled off at atmospheric pressure. Finally, a temperature of 250°C was reached in the still and at this point a negative pressure of 20 mm was created to ensure complete removal of the propylene trimer excess. The residue in the flask weighed 165 g. The theoretical yield for complete monoalkylation is 172 grams. The rest consisted of a syrup which did not crystallise, either in the unmixed state or from a hexane solution (10tfo) at -78°C. This residue had the following analysis:
% C ' fo H io N% C ' fo H io N
Beregnet for C^<H>^<N:>86,96 8,98 k, 06Calculated for C^<H>^<N:>86.96 8.98 k, 06
Funnet 87,76 8,89 4,10 Found 87.76 8.89 4.10
Som det fremgår av ovenstående analyse er produktet vesentlig monoalkylert fenyl-a-naftylamin. Den ovenfor angitte rest i kolben kan destilleres nesten fullstendig mellom 185 og 188°C ved 0,08 mm Hg hvorved man oppnår en blek-kirsebærrød væske. As can be seen from the above analysis, the product is essentially monoalkylated phenyl-a-naphthylamine. The above stated residue in the flask can be distilled almost completely between 185 and 188°C at 0.08 mm Hg whereby a pale cherry red liquid is obtained.
Eksempel 2Example 2
Den i eksempel 1 beskrevne fremgangsmåte ble gjentatt, men med anvendelse av fenyl-P-naftylamin. Man oppnådde en væskeformig blanding av alkylerte f enyl-|3-naf tylaminer . The procedure described in example 1 was repeated, but with the use of phenyl-P-naphthylamine. A liquid mixture of alkylated phenyl-|3-naphthylamines was obtained.
Eksempel 3Example 3
Til 100 deler av en væskeformig, syntetisk ester, nemlig trimetylolpropantriheptanoat ble det tilsatt 1,5 deler av det ifølge eksempel 1 fremstilte reaksjonsprodukt. Den således oppnådde blanding viste seg å ha utmerkede antioksyderende egenskaper ved aldring gjennomført ved forhøyet temperatur. To 100 parts of a liquid, synthetic ester, namely trimethylolpropane triheptanoate, 1.5 parts of the reaction product prepared according to example 1 were added. The mixture thus obtained proved to have excellent antioxidant properties when aged at an elevated temperature.
Eksempel kExample k
Til 100 deler mineralolje ble det tilsatt 2,5 deler av det ifølge eksempel 1 fremstilte reaksjonsprodukt. Den således oppnådde blanding viste seg også å ha utmerkede antioksyderende egenskaper ved aldringsprøver gjennomført ved forhøyet temperatur . 2.5 parts of the reaction product prepared according to example 1 were added to 100 parts of mineral oil. The thus obtained mixture also proved to have excellent antioxidant properties in aging tests carried out at an elevated temperature.
Eksempel 5Example 5
Til 100 deler av et syntetisk, væskeformig hydrocarbon, nemlig polyoktylten, ble det tilsatt 2,0 deler av det ifølge eksempel 2 fremstilte reaksjonsprodukt. Den således oppnådde blanding viste seg å ha utmerkede antioksyderende egenskaper ved aldring gjennomført ved forhøyet temperatur. To 100 parts of a synthetic, liquid hydrocarbon, namely polyoctyltene, 2.0 parts of the reaction product produced according to example 2 were added. The mixture thus obtained proved to have excellent antioxidant properties when aged at an elevated temperature.
Eksempel 6Example 6
Til 100 deler væskeformig, syntetisk hydrocarbon, nemlig polydecen, ble det tilsatt 2,0 deler av det ifølge eksempel 1 fremstilte reaks jonsprodukt. Den således oppnådde blanding viste seg å ha utmerkede antioksyderende egenskaper ved aldring gjen-nomført ved forhøyet temperatur. To 100 parts of liquid, synthetic hydrocarbon, namely polydecene, 2.0 parts of the reaction product produced according to example 1 were added. The mixture thus obtained proved to have excellent antioxidant properties when aged at an elevated temperature.
Eksempel 7Example 7
Til 100 deler va en blanding av 25 deler polyokten ogTo 100 parts was a mixture of 25 parts polyoctene and
75 deler trimetylolpropantriheptanoat, ble det tilsatt 1,7 75 parts of trimethylolpropane triheptanoate, 1.7 were added
deler av det ifølge eksempel 1 fremstilte reaksjonsprodukt.parts of the reaction product prepared according to example 1.
Den således oppnådde blanding hadde utmerkede antioksyderende egenskaper ved aldring gjennomført ved forhøyet temperatur. The mixture thus obtained had excellent antioxidant properties when aged at an elevated temperature.
Eksempel 8Example 8
Til 100 deler av en blanding av 50 deler polyokten ogTo 100 parts of a mixture of 50 parts polyoctene and
en væskeformig,syntetisk ester, nemlig trimetylolpropan triheptanoat ble det tilsatt 1,7 deler av reaksjonsproduktet ifølge eksempel 2. Den således oppnådde blanding viste seg å ha utmerkede antioksyderende egenskaper ved aldring gjennomført ved for-høyet temperatur. a liquid, synthetic ester, namely trimethylolpropane triheptanoate, 1.7 parts of the reaction product according to example 2 were added. The thus obtained mixture proved to have excellent antioxidant properties when aging was carried out at an elevated temperature.
Claims (15)
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JP (1) | JPS5316710A (en) |
BE (1) | BE857312A (en) |
DD (1) | DD131860A5 (en) |
DE (1) | DE2733714A1 (en) |
DK (1) | DK342277A (en) |
FI (1) | FI772243A (en) |
FR (1) | FR2359892A1 (en) |
GB (1) | GB1552720A (en) |
NL (1) | NL7707956A (en) |
NO (1) | NO772682L (en) |
PL (1) | PL199907A1 (en) |
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CA1272183A (en) * | 1986-02-04 | 1990-07-31 | Noboru Ishida | Lubricating oil compositions |
JP2510088B2 (en) * | 1986-06-05 | 1996-06-26 | 日本石油株式会社 | Lubricating oil composition |
JPH01210834A (en) * | 1988-02-18 | 1989-08-24 | Seiko Electronic Components Ltd | Crystal thermal conductivity type vacuum gauge |
CN117529539A (en) | 2021-04-21 | 2024-02-06 | 朗盛公司 | Liquid monoalkylated N-phenyl-alpha-naphthylamine composition and method for producing same |
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BE756024A (en) * | 1969-09-22 | 1971-03-11 | Shell Int Research | ALKYL-SUBSTITUTED PHENYLNAFTYLAMINS AND LUBRICANT COMPOSITIONS THESE CONTAIN |
GB1357744A (en) * | 1971-03-31 | 1974-06-26 | Exxon Research Engineering Co | Antioxidants |
US3773665A (en) * | 1971-11-17 | 1973-11-20 | Mobil Oil Corp | Lubricants containing amine antioxidants |
-
1977
- 1977-07-06 ZA ZA00774076A patent/ZA774076B/en unknown
- 1977-07-11 GB GB28999/77A patent/GB1552720A/en not_active Expired
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GB1552720A (en) | 1979-09-19 |
DD131860A5 (en) | 1978-07-26 |
DE2733714A1 (en) | 1978-02-09 |
JPS5316710A (en) | 1978-02-16 |
SE7708524L (en) | 1978-01-31 |
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PL199907A1 (en) | 1978-04-24 |
FR2359892A1 (en) | 1978-02-24 |
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