US3198739A - Lubricants and polymeric additives therefor - Google Patents
Lubricants and polymeric additives therefor Download PDFInfo
- Publication number
- US3198739A US3198739A US71403A US7140360A US3198739A US 3198739 A US3198739 A US 3198739A US 71403 A US71403 A US 71403A US 7140360 A US7140360 A US 7140360A US 3198739 A US3198739 A US 3198739A
- Authority
- US
- United States
- Prior art keywords
- methacrylate
- copolymer
- vinyl
- oil
- stearyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000654 additive Substances 0.000 title description 7
- 239000000314 lubricant Substances 0.000 title 1
- 229920001577 copolymer Polymers 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 27
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 12
- 239000010688 mineral lubricating oil Substances 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkyl radical Chemical class 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 13
- 239000003599 detergent Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 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 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001924 cycloalkanes Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- QWHNJUXXYKPLQM-UHFFFAOYSA-N dimethyl cyclopentane Natural products CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- LSGPZYLAHPLSBS-UHFFFAOYSA-N 1-[butoxy(chloromethyl)phosphoryl]oxybutane Chemical compound CCCCOP(=O)(CCl)OCCCC LSGPZYLAHPLSBS-UHFFFAOYSA-N 0.000 description 1
- NPNBLTJGRBYCJB-UHFFFAOYSA-N 1-[butoxy(methyl)phosphoryl]oxybutane Chemical compound CCCCOP(C)(=O)OCCCC NPNBLTJGRBYCJB-UHFFFAOYSA-N 0.000 description 1
- SUGMXDMMEJYWBB-UHFFFAOYSA-N 1-[butoxy(trichloromethyl)phosphoryl]oxybutane Chemical compound CCCCOP(=O)(C(Cl)(Cl)Cl)OCCCC SUGMXDMMEJYWBB-UHFFFAOYSA-N 0.000 description 1
- OOMQAYMCTYABQN-UHFFFAOYSA-N 1-chloro-2-dibutoxyphosphorylbenzene Chemical compound CCCCOP(=O)(OCCCC)C1=CC=CC=C1Cl OOMQAYMCTYABQN-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- GBMSVKSVQIQOJG-UHFFFAOYSA-N 1-ethenoxyhexacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCOC=C GBMSVKSVQIQOJG-UHFFFAOYSA-N 0.000 description 1
- AESMKCQAJQGEMT-UHFFFAOYSA-N 1-ethenoxytetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCOC=C AESMKCQAJQGEMT-UHFFFAOYSA-N 0.000 description 1
- YVDYGBNMUBYYDF-UHFFFAOYSA-N 1-ethenoxytridecane Chemical compound CCCCCCCCCCCCCOC=C YVDYGBNMUBYYDF-UHFFFAOYSA-N 0.000 description 1
- QUBBAXISAHIDNM-UHFFFAOYSA-N 1-ethyl-2,3-dimethylbenzene Chemical class CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- AHVCKSSYNJYSIQ-UHFFFAOYSA-N 1-hydroxypentyl 2-methylprop-2-enoate Chemical compound CCCCC(O)OC(=O)C(C)=C AHVCKSSYNJYSIQ-UHFFFAOYSA-N 0.000 description 1
- NHCREQREVZBOCH-UHFFFAOYSA-N 1-methyl-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene Chemical class C1CCCC2C(C)CCCC21 NHCREQREVZBOCH-UHFFFAOYSA-N 0.000 description 1
- NSRJCKNAJOEJMR-UHFFFAOYSA-N 1-prop-2-enoxydodecane Chemical compound CCCCCCCCCCCCOCC=C NSRJCKNAJOEJMR-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- PABGQABTFFNYFH-UHFFFAOYSA-N 2-methyl-n-octadecylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C(C)=C PABGQABTFFNYFH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- XNXIYYFOYIUJIW-UHFFFAOYSA-N 3-methylbutylbenzene Chemical compound CC(C)CCC1=CC=CC=C1 XNXIYYFOYIUJIW-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- FUUGBGSHEIEQMS-UHFFFAOYSA-N 4a,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalene Chemical class C1CCCC2(C)CCCCC21C FUUGBGSHEIEQMS-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VCZXRQFWGHPRQB-UHFFFAOYSA-N CC(C)CC(C)(C)C.CC(C)CC(C)(C)C Chemical compound CC(C)CC(C)(C)C.CC(C)CC(C)(C)C VCZXRQFWGHPRQB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- BQMQLJQPTQPEOV-UHFFFAOYSA-N OP(=O)OC=C Chemical class OP(=O)OC=C BQMQLJQPTQPEOV-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- QXVVOCXSPOTJDT-UHFFFAOYSA-N benzene;2-tert-butylperoxy-2-methylpropane Chemical compound C1=CC=CC=C1.CC(C)(C)OOC(C)(C)C QXVVOCXSPOTJDT-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 150000005195 diethylbenzenes Chemical class 0.000 description 1
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- YNEBMXYYGXQPKT-UHFFFAOYSA-N ethenyl 2-chlorooctadecanoate Chemical compound ClC(C(=O)OC=C)CCCCCCCCCCCCCCCC YNEBMXYYGXQPKT-UHFFFAOYSA-N 0.000 description 1
- WBQBZPORCXPNKS-UHFFFAOYSA-N ethenyl 2-cyanooctadecanoate Chemical compound C(#N)C(C(=O)OC=C)CCCCCCCCCCCCCCCC WBQBZPORCXPNKS-UHFFFAOYSA-N 0.000 description 1
- YTRLJAOGYUYCDH-UHFFFAOYSA-N ethenyl 9,10-dihydroxyoctadecanoate Chemical compound CCCCCCCCC(O)C(O)CCCCCCCC(=O)OC=C YTRLJAOGYUYCDH-UHFFFAOYSA-N 0.000 description 1
- LTDFJOPAUCPEEN-UHFFFAOYSA-N ethenyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC=C LTDFJOPAUCPEEN-UHFFFAOYSA-N 0.000 description 1
- VHCIMSREIXSASU-UHFFFAOYSA-N ethenyl nonadecanoate Chemical compound CCCCCCCCCCCCCCCCCCC(=O)OC=C VHCIMSREIXSASU-UHFFFAOYSA-N 0.000 description 1
- LCXVQGZZGUOSLZ-UHFFFAOYSA-N ethenyl pentadecanoate Chemical compound CCCCCCCCCCCCCCC(=O)OC=C LCXVQGZZGUOSLZ-UHFFFAOYSA-N 0.000 description 1
- ZQZUENMXBZVXIZ-UHFFFAOYSA-N ethenyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC=C ZQZUENMXBZVXIZ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229940072106 hydroxystearate Drugs 0.000 description 1
- NGYRYRBDIPYKTL-UHFFFAOYSA-N icosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C=C NGYRYRBDIPYKTL-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- HOZLHJIPBBRFGM-UHFFFAOYSA-N n-dodecyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCCCNC(=O)C(C)=C HOZLHJIPBBRFGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 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 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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Definitions
- Polymers of this type may be represented by the Formula I where R and R are alkyl radicals as defined above, Y may be a C alkyl radical or a polar radical such as an ester, amide, amine, or phosphate radical or the like, m and m; are Whole numbers of at least 2 each and u may be zero or a Whole number, the ratio of m to m may vary from 1:10 to :1, preferably from 5:1 to 2:1 and the ratio of m+m to n when n is a whole number may vary from 10:1 to 5:1, respectively.
- the molecular weight of the polymer varies from about one thousand to about one million, preferably from 10,000 to 500,000.
- the first polymerizable monomer group includes acrylic and alkacrylic esters of aliphatic alcohols of at least 8 carbon atoms, preferably of from 10 to 20 carbon atoms, and include, inter alia, decyl acrylate, lauryl acrylate, stearyl acrylate, eicosanyl acrylate, docosanyl acrylate, decyl methacrylate, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate, and the like, and mixtures thereof.
- the other polymerizable group includes omega-hydroxyesters of acrylic or alkacrylic acid and dihydroxy alkanes which may be straight or branch-chain, preferably alpha,
- vinyl ethers vinyl dodecyl ether, vinyl tridecyl ether, vinyl tetracosyl ether, vinyl hexacosyl ether; allyl esters or ethers, allyl stearate, allyl dodecyl ether; amido esters, e.g., N-lauryl methacrylamide, N-stearyl methacrylamide, N,N'-di-.stearyl methacrylamide; vinylpyridines, e.g., 4- vinylpyridine, 2-methyl-5-vinylpyridine, vinylpyrrolidone, vinyl phosphonates and allyl phosphates, e.g., tn'methallyl phosphate, bis-chloroethyl vinyl phosphonate and and mixtures thereof.
- vinylpyridines e.g., 4- vinylpyridine, 2-methyl-5-vinylpyridine, vinylpyrrolidone, vinyl phosphonates and allyl phosphates, e
- the polymerization may be effected in the presence of a substantially inert liquid and in the presence of an oxygen-yielding catalyst at a temperature in the range of 50 to C., preferably between 6090 C.
- Suitable liquid reaction media are various classes of hydrocarbons or their mixtures which are liquid and substantially inert under the polymerization conditions of the present process.
- Certain classes of aliphatic hydrocarbons can be employed as'a liquid hydrocarbon reaction medium in the present process.
- various saturated hydrocarbons alkanes and cycloalkanes
- Either pure alkanes or cycloalkanes or commercially available mixtures, freed of catalyst poisons, may be employed.
- liquid or liquefied alkanes such as n-pentane, n-hexane, 2,3-dimethylbutane, n-octane, isooctane (2,2,4- trimethylpentane), n-decane, n-dodecane, cyclohexane, methylcyclohexane, dimethylcyclopentane, ethylcyclohexane, decalin, methyldecalins, dimethyldecalins and the like.
- alkanes such as n-pentane, n-hexane, 2,3-dimethylbutane, n-octane, isooctane (2,2,4- trimethylpentane), n-decane, n-dodecane, cyclohexane, methylcyclohexane, dimethylcyclopentane, ethylcyclohexane
- aromatic hydrocarbon series particularly the mononuclear aromatic hydrocarbons, viz., benzene, toluene, xylenes, mesitylene and xylene-p-cymene mixtures can also be employed.
- aromatic hydrocarbons as ethylbenzene, isopropylbenzene, sec-butylbenzene, t-butylbenzene, ethyltoluene, ethylxylenes, hemimellitene, pseudocumene, prehnitene, isodurene, diethylbenzenes, isoamylbenzene and the like.
- Suitable aromatic hydrocarbon fractions can be obtained by the selective extraction of aromatic naphthas from hydroforming operations as distillates or bottoms, from cyclo stock fractions of cracking operations, etc.
- alkyl naphthalenes which are liquid under the polymerization reaction con recovered and the copolymer exhibited excellent detergent properties.
- acry a VIII do ..do Triallyl phosphate" Heptene. do 80 100,000 IX w-Hydlrotxyamyl methdo Vinyl pyrrolidone..- Benzene do 80 200, 000
- an oil-soluble copolymer of stearyl methacrylate/ 2 methyl-S-vinylpyridine/ omega hydroxyamyl methacrylate having a moiecular weight of 100,000 was
- additional improvements with respect to oxidation stability and scufiing inhibition can be imparted to the oil compositions containing the copolymers of this invention by incorporating small amounts (0.01%- 2%, preferably 0.1%-1%) of phenolic antioxidants such as alkylphenols, e.g., 2,6-ditertbutyl-4-methylphenol or p,p'-methylene bisphenols such as 4,4-rnethylene bis (2,6-ditertbutylphenol) or arylamines such as phenylalpha-naphthylamine and mixtures thereof.
- phenolic antioxidants such as alkylphenols, e.g., 2,6-ditertbutyl-4-methylphenol or p,p'-methylene bisphenols such as 4,4-rn
- Anti-scuifing agents include organic phosphites, phosphates, phosphonates and their thio-derivatives, such as C alkyl phosphites, or phosphonates, e.g., diand tributyl, octyl, lauryl, stearyl, cyclohexyl, benzyl, cresyl, phenyl, phosphites or phosphates, as well as their thio-derivatives, P S -terpene reaction product, e.g., P S -pine oil reaction product and alkali metal salts thereof such as a potassium salt of a P S -terpene reaction product, phosphonates such as dibutyl methanephosphonate, dibutyl trichloromethanephosphonate, dibutyl monochloromethanephosphonate, dibutyl chlorobenzenephosphonate, and the like.
- the polymeric additives of this invention improve various mineral oil products by the incorporation of a minor amount (0.01% to 5%, preferably 0.1% to 3% by weight) of the additive.
- they may be used to improve transformer oils, turbine oils, mineral lubricating oils, industrial oils and the like.
- lubricating oils range from SAE 5W viscosity grade .to SAE 140 grade and are derived from parafiinic, naphthenic or asphaltic base crudes.
- Representative oils are refined high viscosity index mineral oils having a viscosity of F of 100 to 250 SUS.
- a typical mineral lubricating oil (X) of this type had the following properties:
- Lubricating compositions of this invention are particularly applicable for high temperature, high speed use as in aviation engines, automotive engines, truck engines
- Composition A Percent wt. 11 d 1
- a mineral lubricating oil composition consisting es- 1e c 01 mer 2 sentially of a major amount of mineral lubricating oil Mineral lubricgfig on 6 Balance and from about 0.01% to by weight of an oil-soluble Com osition copolymer of a C1240 alkyl methacrylate and an ester of g 1e Co 01 mar 2 methacrylic acid and an alpha, omega C alkanediol in Minergl z z oil Balance the ratio of 1:10 to 10: 1, respectively, said copolyiner hav- Com osition ing a molecular weight of from 10,000 to 500,000.
- a mineral lubricating oil composition consisting es- Minergl lubricagny on Balance sentially of major amount of mineral lubricating Oil and Com osition g 1 from about 0.01% to 5% by weight of an oil-soluble g 1e co olymer 2 copolymer of a C1240 alkyl methacrylate and an ester of Mineral lubricgfing oil Balance methacrylic acid and 1,5-pentanediol in the ratio of 1:10 Composition to 10:1, respectively, said copolymer having a molecular Example copolymer 3 weight of from 10,000 to 500,000.
- a mineral lubricating oil composition consistlng es- Mineml lubricating (aviation oil 65 sentially of a major amount of mineral lubricating oil grade) Balance and from about 0.01% to 5% by weight of an oil-soluble comnosifion copolymer of stearyl methacrylate and an ester of methajixamnle I'copdymer 5 crylic acid and 1,5-pentanediol in the ratio of 1:10 to 4 4, methy1ene his, g ';gg g gfl ggf 0 5 10:1, respectively, said copolymer having a molecular Tricresyl phosphate weight of from 10,000 to 500,000.
- a mineral lubricating oil composition consisting esi "f "i sentially of a major amount of mineral lubricating oil in order to demonstrate the utility and nnproved propand from about 0.01% to 5% by weight of an oil-soluble erties of this invention, the c0mpos1t1ons identified in copolymer of stearyl methacrylate, lauryl methacrylate, Table I were tested in the Chevrolet V8 Sludgmg Test, an ester of methacrylic acid and 1,5-pentanediol in the modified EX-3 test described in CRC Progress Report ratio of 1:10 to 10:1, respectively, said copolymer having No. 3, June 1, 1957, and the results were as follows: a molecular weight of from 10,000 to 500,000.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71403A US3198739A (en) | 1960-11-25 | 1960-11-25 | Lubricants and polymeric additives therefor |
| FR879828A FR1306897A (fr) | 1960-11-25 | 1961-11-23 | Composés polymères convenant comme additifs pour huile lubrifiante, et huiles lubrifiantes contenant ces composés |
| DES76807A DE1237721B (de) | 1960-11-25 | 1961-11-23 | Schmiermittel |
| GB41977/61A GB947800A (en) | 1960-11-25 | 1961-11-23 | Polymeric compounds suitable as lubricating oil additives and lubricating oils containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71403A US3198739A (en) | 1960-11-25 | 1960-11-25 | Lubricants and polymeric additives therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3198739A true US3198739A (en) | 1965-08-03 |
Family
ID=22101082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US71403A Expired - Lifetime US3198739A (en) | 1960-11-25 | 1960-11-25 | Lubricants and polymeric additives therefor |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3198739A (de) |
| DE (1) | DE1237721B (de) |
| GB (1) | GB947800A (de) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3377285A (en) * | 1965-05-07 | 1968-04-09 | Shell Oil Co | Non-thickening oil concentrates |
| JPS5830357B1 (de) * | 1971-03-05 | 1983-06-28 | Shell Int Research | |
| EP0418610A1 (de) * | 1989-09-09 | 1991-03-27 | Röhm Gmbh | Dispergierwirksame ViskositÀ¤ts-Index-Verbesserer |
| EP0570093A1 (de) * | 1992-03-20 | 1993-11-18 | Rohm And Haas Company | Aschefreie Dispersante Poly(Meth)Acrylat-Polymere |
| EP0569639A1 (de) * | 1992-03-20 | 1993-11-18 | Rohm And Haas Company | Dispergierende Polymethacrylat-Viskositätsverbesserer |
| US5726136A (en) * | 1994-10-19 | 1998-03-10 | Agip Petroli S.P.A. | Multifunctional additive for lubricating oils compatible with fluoroelastomers |
| US6475964B1 (en) * | 1994-08-03 | 2002-11-05 | Roehm Gmbh & Co. Kg | Motor oil with high dispersivity and good wear protection characteristics |
| WO2009095483A3 (en) * | 2008-01-30 | 2009-10-29 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791942R (fr) * | 1971-05-05 | 1973-05-28 | Sun Oil Co Pennsylvania | Lubrification par |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892819A (en) * | 1956-03-29 | 1959-06-30 | California Research Corp | Detergent copolymers |
| US2892790A (en) * | 1956-02-03 | 1959-06-30 | California Research Corp | Lubricant composition |
| US2892792A (en) * | 1956-02-03 | 1959-06-30 | California Research Corp | Lubricant composition |
| US2913439A (en) * | 1955-12-01 | 1959-11-17 | Shell Dev | Hydroxy-containing copolymers and their preparation |
| CA590443A (en) * | 1960-01-12 | T. Stewart William | Lubricant composition | |
| US2927013A (en) * | 1956-03-29 | 1960-03-01 | California Research Corp | Fuel composition |
| US2949445A (en) * | 1958-05-06 | 1960-08-16 | Du Pont | Methyl methacrylate polymers containing amino residues |
| US2980658A (en) * | 1956-05-14 | 1961-04-18 | Baker Chem Co J T | Copolymer of an alkyl methacrylate and an alpha-acyloxystyrene, and method for preparing same |
| US2994663A (en) * | 1959-08-10 | 1961-08-01 | California Research Corp | Lubricant containing copolymer viscosity index improver |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB770771A (en) * | 1953-05-18 | 1957-03-27 | California Research Corp | Copolymeric dispersants and lubricant compositions containing them |
| NL91489C (de) * | 1953-05-25 | |||
| BE538017A (de) * | 1954-05-10 | |||
| NL102110C (de) * | 1955-09-26 |
-
1960
- 1960-11-25 US US71403A patent/US3198739A/en not_active Expired - Lifetime
-
1961
- 1961-11-23 DE DES76807A patent/DE1237721B/de active Pending
- 1961-11-23 GB GB41977/61A patent/GB947800A/en not_active Expired
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA590443A (en) * | 1960-01-12 | T. Stewart William | Lubricant composition | |
| US2913439A (en) * | 1955-12-01 | 1959-11-17 | Shell Dev | Hydroxy-containing copolymers and their preparation |
| US2892790A (en) * | 1956-02-03 | 1959-06-30 | California Research Corp | Lubricant composition |
| US2892792A (en) * | 1956-02-03 | 1959-06-30 | California Research Corp | Lubricant composition |
| US2892819A (en) * | 1956-03-29 | 1959-06-30 | California Research Corp | Detergent copolymers |
| US2927013A (en) * | 1956-03-29 | 1960-03-01 | California Research Corp | Fuel composition |
| US2980658A (en) * | 1956-05-14 | 1961-04-18 | Baker Chem Co J T | Copolymer of an alkyl methacrylate and an alpha-acyloxystyrene, and method for preparing same |
| US2949445A (en) * | 1958-05-06 | 1960-08-16 | Du Pont | Methyl methacrylate polymers containing amino residues |
| US2994663A (en) * | 1959-08-10 | 1961-08-01 | California Research Corp | Lubricant containing copolymer viscosity index improver |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3377285A (en) * | 1965-05-07 | 1968-04-09 | Shell Oil Co | Non-thickening oil concentrates |
| JPS5830357B1 (de) * | 1971-03-05 | 1983-06-28 | Shell Int Research | |
| EP0418610A1 (de) * | 1989-09-09 | 1991-03-27 | Röhm Gmbh | Dispergierwirksame ViskositÀ¤ts-Index-Verbesserer |
| US5188770A (en) * | 1989-09-09 | 1993-02-23 | Rphm GmbH | Viscosity index improver having detergent properties |
| EP0570093A1 (de) * | 1992-03-20 | 1993-11-18 | Rohm And Haas Company | Aschefreie Dispersante Poly(Meth)Acrylat-Polymere |
| EP0569639A1 (de) * | 1992-03-20 | 1993-11-18 | Rohm And Haas Company | Dispergierende Polymethacrylat-Viskositätsverbesserer |
| US6475964B1 (en) * | 1994-08-03 | 2002-11-05 | Roehm Gmbh & Co. Kg | Motor oil with high dispersivity and good wear protection characteristics |
| US5726136A (en) * | 1994-10-19 | 1998-03-10 | Agip Petroli S.P.A. | Multifunctional additive for lubricating oils compatible with fluoroelastomers |
| WO2009095483A3 (en) * | 2008-01-30 | 2009-10-29 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1237721B (de) | 1967-03-30 |
| GB947800A (en) | 1964-01-29 |
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