DE2017253A1 - Verwendung von alkylierten Diphenylaminen als Stabilisatoren - Google Patents

Verwendung von alkylierten Diphenylaminen als Stabilisatoren

Info

Publication number: DE2017253A1
Authority: DE; Germany
Prior art keywords: tert; diphenylamine; parts; acid; catalyst
Prior art date: 1969-04-11
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.): Pending

Application number

DE19702017253

Other languages

German (de)

English (en)

Inventor

Brian Royton Lancashire Holt (Großbritannien)

Original Assignee

J.R. Geigy AG, Basel (Schweiz)

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.)

1969-04-11

Filing date

1970-04-10

Publication date

1970-10-15

1970-04-10 Application filed by J.R. Geigy AG, Basel (Schweiz) filed Critical J.R. Geigy AG, Basel (Schweiz)

1970-10-15 Publication of DE2017253A1 publication Critical patent/DE2017253A1/de

Status Pending legal-status Critical Current

Links

DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title description 54
239000003381 stabilizer Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 14
239000000314 lubricant Substances 0.000 claims description 14
239000011368 organic material Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 44
239000003054 catalyst Substances 0.000 description 30
229940035422 diphenylamine Drugs 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 22
150000001336 alkenes Chemical class 0.000 description 22
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
-1 Diphenyl amines Chemical class 0.000 description 18
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 17
239000003963 antioxidant agent Substances 0.000 description 16
238000005804 alkylation reaction Methods 0.000 description 15
239000003921 oil Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
230000003078 antioxidant effect Effects 0.000 description 12
239000000654 additive Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000000463 material Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 9
239000007788 liquid Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
229920001971 elastomer Polymers 0.000 description 8
239000000155 melt Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
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238000007792 addition Methods 0.000 description 7
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238000001953 recrystallisation Methods 0.000 description 7
238000005727 Friedel-Crafts reaction Methods 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229910052782 aluminium Inorganic materials 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
235000011007 phosphoric acid Nutrition 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000007858 starting material Substances 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
239000012964 benzotriazole Substances 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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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 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000032683 aging Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229920000180 alkyd Polymers 0.000 description 2
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PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
230000002528 anti-freeze Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
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JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
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MHJCZOMOUCUAOI-UHFFFAOYSA-N n-tert-butyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C(C)(C)C)C1=CC=CC=C1 MHJCZOMOUCUAOI-UHFFFAOYSA-N 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
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GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
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HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
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JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
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ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-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
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
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OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 description 1
IWASLBFJTMJYHF-UHFFFAOYSA-N 5-(2h-benzotriazol-5-ylmethyl)-2h-benzotriazole Chemical compound C1=CC2=NNN=C2C=C1CC1=CC2=NNN=C2C=C1 IWASLBFJTMJYHF-UHFFFAOYSA-N 0.000 description 1
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125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
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WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
239000000473 propyl gallate Substances 0.000 description 1
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235000010388 propyl gallate Nutrition 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
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FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
229920005573 silicon-containing polymer Polymers 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000010802 sludge Substances 0.000 description 1
HLWRUJAIJJEZDL-UHFFFAOYSA-M sodium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical compound [Na+].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC([O-])=O HLWRUJAIJJEZDL-UHFFFAOYSA-M 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
239000008117 stearic acid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
238000005496 tempering Methods 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000019303 thiodipropionic acid Nutrition 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical class C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
239000013638 trimer Substances 0.000 description 1
QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
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229930003231 vitamin Natural products 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
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ZUBNXRHITOZMOO-UHFFFAOYSA-N zinc;octadecanoic acid;oxygen(2-) Chemical compound [O-2].[Zn+2].CCCCCCCCCCCCCCCCCC(O)=O ZUBNXRHITOZMOO-UHFFFAOYSA-N 0.000 description 1

Classifications

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- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
- 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
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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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
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- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
- 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
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- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
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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
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- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
- 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
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- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts thereof
- 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
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- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
- C10M2227/082—Pb compounds
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/10—Groups 5 or 15
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Lubricants (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DE19702017253 1969-04-11 1970-04-10 Verwendung von alkylierten Diphenylaminen als Stabilisatoren Pending DE2017253A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB08617/69A GB1236740A (en)	1969-04-11	1969-04-11	Tertiary alkylated diphenylamines and their uses as antioxidants

Publications (1)

Publication Number	Publication Date
DE2017253A1 true DE2017253A1 (de)	1970-10-15

Family

ID=10115531

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19702017253 Pending DE2017253A1 (de)	1969-04-11	1970-04-10	Verwendung von alkylierten Diphenylaminen als Stabilisatoren

Country Status (6)

Country	Link
US (1)	US3655559A (fr)
BE (1)	BE748783A (fr)
DE (1)	DE2017253A1 (fr)
FR (1)	FR2038396A1 (fr)
GB (1)	GB1236740A (fr)
NL (1)	NL7005208A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
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EP0260651A3 (fr) *	1986-09-19	1988-09-07	The B.F. GOODRICH Company	Procédé de préparation d'une composition de diphénylamines ortho-éthylées, para-butylées et -octylées

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GB1546712A (en) *	1976-07-21	1979-05-31	Ici Ltd	Manufacture of n,n,n,n',n' - tetraphenyladiaminomethane antioxidants
US4298481A (en) *	1979-02-23	1981-11-03	Tenneco Chemicals, Inc.	High temperature grease compositions
US4440671A (en) *	1982-03-31	1984-04-03	Union Carbide Corporation	Compositions of hydrocarbon-substituted diphenyl amines and high molecular weight polyethylene glycols; and the use thereof as water-tree retardants for polymers
EP0097118A3 (fr) *	1982-06-10	1984-07-25	Ciba-Geigy Ag	Liquides antioxydants pour lubrifiants et élastomères
US4414348A (en) *	1983-01-26	1983-11-08	The Goodyear Tire & Rubber Company	Stabilized polyester compositions
US4739121A (en) *	1984-05-24	1988-04-19	The B. F. Goodrich Company	Process for otho- and para-alkylating diphenylamines
US5180514A (en) *	1985-06-17	1993-01-19	The Clorox Company	Stabilizing system for liquid hydrogen peroxide compositions
US4837259A (en) *	1987-09-25	1989-06-06	Uniroyal Chemical Company, Inc.	Polypropylene stabilized against oxidative degradation with mixtures of diarylamine derivatives and sterically hindered phenols
US4797511A (en) *	1987-09-25	1989-01-10	Uniroyal Chemical Company, Inc.	Polyethylene stabilized by mixture of hindered phenol and amine antioxidants
US4925889A (en) *	1987-09-25	1990-05-15	Uniroyal Chemical Company, Inc.	Stabilized carbon black loaded polyolefins
EP0407124A1 (fr) *	1989-07-07	1991-01-09	Tonen Corporation	Composition d'huile lubrifiante
KR0173792B1 (ko) *	1990-09-13	1999-03-20	월터콜리웨인; 한스-피터 위트린	페노티아진을 함유하는 혼합물 및 조성물
US5373028A (en) *	1991-08-20	1994-12-13	The Dow Chemical Company	Polyurethane foams having reduced visible emissions during curing
DE4214653A1 (de) *	1992-05-02	1993-11-04	Henkel Kgaa	Motorengrundoele mit verbesserter dichtungsvertraeglichkeit
US5321159A (en) *	1992-12-18	1994-06-14	The B. F. Goodrich Company	Decolorization of alkylated diarylamines
JPH07109477A (ja) *	1993-10-15	1995-04-25	Oronaito Japan Kk	農業機械もしくは建設機械用の共通潤滑作動油
DE69405410T2 (de)	1993-12-15	1998-03-19	Goodrich Co B F	Stabilisatormischung für synthetisches estergleitmittel
US5571453A (en) *	1994-10-25	1996-11-05	Uniroyal Chemical Company, Inc.	Stabilized polyether polyol and polyurethane foam obtained therefrom
GB2294696A (en) *	1994-11-04	1996-05-08	Exxon Research Engineering Co	Marine lubricant composition
US5489711A (en) *	1994-12-20	1996-02-06	The B. F. Goodrich Company	Synthetic lubricant antioxidant from monosubstituted diphenylamines
US5672752A (en) *	1995-09-13	1997-09-30	The Bfgoodrich Company	Liquid alkylated diphenylamine antioxidant
US5750787A (en) *	1995-09-13	1998-05-12	B. F. Goodrich Company	Liquid alkylated diphenylamine antioxidant
US6573224B2 (en) *	1997-01-03	2003-06-03	Bardahl Manufacturing Corporation	Two-cycle engine lubricant composition comprising an ester copolymer and a diester
US5834544A (en) *	1997-10-20	1998-11-10	Uniroyal Chemical Company, Inc.	Organic materials stabilized by compounds containing both amine and hindered phenol functional functionalities
US6204412B1 (en)	1999-04-16	2001-03-20	The B. F. Goodrich Company	Method of manufacturing alkylated diphenylamine compositions and products thereof
US8003583B2 (en) *	2005-12-21	2011-08-23	Chevron Oronite Company Llc	Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions
US7285518B2 (en) *	2005-12-21	2007-10-23	Chevron Oronite Company Llc	Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions
US7501386B2 (en) *	2005-12-21	2009-03-10	Chevron Oronite Company, Llc	Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine
US8939184B2 (en) *	2006-12-21	2015-01-27	Bridgestone Americas Tire Operations, Llc	Rubber composition and pneumatic tire using same
US7683017B2 (en) *	2007-06-20	2010-03-23	Chevron Oronite Company Llc	Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine
EP2077315B1 (fr)	2007-12-20	2012-10-31	Chevron Oronite Company LLC	Compositions d'huile de lubrification contenant un antioxydant de diamine tetraalkyl-napthalène-1,8 et de diarylamine
US8623798B2 (en) *	2007-12-20	2014-01-07	Chevron Oronite Company Llc	Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant
CN102112434A (zh) *	2008-08-08	2011-06-29	雅宝公司	辛基化苯基-α-萘胺产物混合物及具有高辛基化苯基-α-萘胺含量的该等混合物的制备
JP5761470B2 (ja) *	2013-07-11	2015-08-12	Nok株式会社	ニトリルゴム組成物
US10323017B2 (en)	2015-02-06	2019-06-18	Alma Mater Studiorum—Universita di Bologna	Antioxidants and methods to maximize performance
GB2579405B (en)	2018-11-30	2022-09-14	Si Group Switzerland Chaa Gmbh	Antioxidant compositions
CN116601263B (zh) *	2020-11-17	2025-07-01	松原实业有限公司	性能提高的包含烷基化二苯胺的组合物
TW202311225A (zh)	2021-06-25	2023-03-16	韓商松原產業股份有限公司	O-烷基化位阻抗氧化劑

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Publication number	Priority date	Publication date	Assignee	Title
US2009480A (en) *	1932-06-10	1935-07-30	Goodrich Co B F	Antioxidant
NL248188A (fr) *	1959-02-11
US3282840A (en) *	1962-11-29	1966-11-01	Eastman Kodak Co	Stable lubricating composition and inhibitor mixture therefor

1969
- 1969-04-11 GB GB08617/69A patent/GB1236740A/en not_active Expired
1970
- 1970-04-09 US US27176A patent/US3655559A/en not_active Expired - Lifetime
- 1970-04-10 BE BE748783D patent/BE748783A/fr unknown
- 1970-04-10 FR FR7012990A patent/FR2038396A1/fr not_active Withdrawn
- 1970-04-10 NL NL7005208A patent/NL7005208A/xx unknown
- 1970-04-10 DE DE19702017253 patent/DE2017253A1/de active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0260651A3 (fr) *	1986-09-19	1988-09-07	The B.F. GOODRICH Company	Procédé de préparation d'une composition de diphénylamines ortho-éthylées, para-butylées et -octylées

Also Published As

Publication number	Publication date
FR2038396A1 (fr)	1971-01-08
GB1236740A (en)	1971-06-23
US3655559A (en)	1972-04-11
BE748783A (fr)	1970-10-12
NL7005208A (fr)	1970-10-13

Legal Events

Date	Code	Title	Description
1978-07-13	OHW	Rejection

Publication	Publication Date	Title
DE2017253A1 (de)	1970-10-15	Verwendung von alkylierten Diphenylaminen als Stabilisatoren
EP0149422B1 (fr)	1989-05-17	Préparation d'antioxidant
CA1219584A (fr)	1987-03-24	Stabilisateurs a base de derives de substitution en n de (4-hydroxyphenylthiomethyl)-amine ou -ureide
EP0165209B1 (fr)	1989-07-19	Phénols o'-substitués, o,p-bifonctionnalisés
EP1411044B1 (fr)	2007-10-31	Huiles lubrifiantes et solutions de polyols stabilisés contre l'oxydation
DE2211805A1 (de)	1972-09-28	Substituierte Phenothiazine
EP0214932B1 (fr)	1988-09-28	Compositions lubrifiantes et fluides hydrauliques comprenant des dérivés soufrés de phénol et dérivés soufrés de phénol
DE2638324C3 (de)	1982-01-14	Kompressorenöl
US3773830A (en)	1973-11-20	N-aroyl-n'-(alkylhydroxyphenyl)alkanoylhydrazines
DE69408694T2 (de)	1998-10-15	Ein polymer-antioxidant enthaltende schmiermittel zusammensetzung
US4741846A (en)	1988-05-03	2,4,6-trifunctionalized phenols
US3491157A (en)	1970-01-20	Cycloalkylidenebis(cycloalkylphenols)
EP0286595A2 (fr)	1988-10-12	Composés anti-oxydants contenant du sulfure pour lubrifiants et élastomères
DE2250351A1 (de)	1973-04-19	Antioxydans-zusammensetzungen
CA1073923A (fr)	1980-03-18	Derives d'acide salicylique
CA1210402A (fr)	1986-08-26	Stabilisateurs a base de (4-hydroxyphenylthio)imide
DE3446646A1 (de)	1985-07-04	Stabilisierung von polyalkylenglykolen
EP1067124A1 (fr)	2001-01-10	Procédé de préparation d'un mélange de phénothiazines et diphénylamines alkylées
EP0097118A2 (fr)	1983-12-28	Liquides antioxydants pour lubrifiants et élastomères
DE602004004093T2 (de)	2007-09-06	Alkylierte iminodibenzyle als antioxidationsmittel
CA1234138A (fr)	1988-03-15	Stabilisateurs a base de derives de substitution de 4-hydroxyphenylthio-benzoate
DE2711654C2 (fr)	1992-09-03
US4007159A (en)	1977-02-08	Organic substrates stabilized by nitroalkane based hindered phenol compounds
DE2110627A1 (de)	1971-09-30	Diphenylnitroxyde und ihre Verwendung als Stabilisatoren
DE2250397A1 (de)	1973-04-19	Antioxydans-zusammensetzungen

DE2017253A1 - Verwendung von alkylierten Diphenylaminen als Stabilisatoren - Google Patents

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ID=10115531

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Cited By (1)

Families Citing this family (39)

Family Cites Families (3)

Cited By (1)

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