US3337458A - Oil-soluble polymers and compositions containing them - Google Patents
Oil-soluble polymers and compositions containing them Download PDFInfo
- Publication number
- US3337458A US3337458A US539633A US53963366A US3337458A US 3337458 A US3337458 A US 3337458A US 539633 A US539633 A US 539633A US 53963366 A US53963366 A US 53963366A US 3337458 A US3337458 A US 3337458A
- Authority
- US
- United States
- Prior art keywords
- oil
- parts
- copolymer
- solution
- methacrylate
- 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
- 239000000203 mixture Substances 0.000 title claims description 81
- 229920000642 polymer Polymers 0.000 title claims description 61
- 239000000178 monomer Substances 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 16
- 239000000314 lubricant Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 11
- 239000000446 fuel Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 239000012530 fluid Substances 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 114
- 229920001577 copolymer Polymers 0.000 description 62
- 239000003921 oil Substances 0.000 description 56
- 239000000243 solution Substances 0.000 description 56
- 239000002270 dispersing agent Substances 0.000 description 26
- -1 aralkyl alcohols Chemical class 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- 238000012360 testing method Methods 0.000 description 20
- 239000010802 sludge Substances 0.000 description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 14
- 239000002199 base oil Substances 0.000 description 12
- 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 11
- HJSMBDKULYJQKM-UHFFFAOYSA-N hexacosan-13-yl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCC(OC(=O)C(C)=C)CCCCCCCCCCCC HJSMBDKULYJQKM-UHFFFAOYSA-N 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 11
- 150000003462 sulfoxides Chemical class 0.000 description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- 238000007334 copolymerization reaction Methods 0.000 description 8
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 8
- 239000003599 detergent Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 7
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 7
- 238000001030 gas--liquid chromatography Methods 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 230000001050 lubricating effect Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 239000010687 lubricating oil Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000295 fuel oil Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000005529 alkyleneoxy group Chemical group 0.000 description 4
- VSQISCXHUXHKMC-UHFFFAOYSA-M benzyl-methyl-[2-(2-phenoxyethoxy)ethyl]-(2,2,4,4-tetramethylpentyl)azanium chloride hydrate Chemical compound O.[Cl-].C(C)(C)(CC(C)(C)C)C[N+](C)(CC1=CC=CC=C1)CCOCCOC1=CC=CC=C1 VSQISCXHUXHKMC-UHFFFAOYSA-M 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229940043348 myristyl alcohol Drugs 0.000 description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000012857 radioactive material Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 2
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 2
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 2
- UYAFNMBGMXYWSZ-UHFFFAOYSA-N 4-(dimethylamino)-2-methylidenebutanamide Chemical compound CN(C)CCC(=C)C(N)=O UYAFNMBGMXYWSZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VKXLSZNHJXYZQV-HEFFKOSUSA-N CCCCCCCCCCCCC(CCCCCCCCCCCC)CCCCCCCCCCCCCOC(/C=C/C(O)=O)=O Chemical compound CCCCCCCCCCCCC(CCCCCCCCCCCC)CCCCCCCCCCCCCOC(/C=C/C(O)=O)=O VKXLSZNHJXYZQV-HEFFKOSUSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940091181 aconitic acid Drugs 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000010771 distillate fuel oil Substances 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000004992 fission Effects 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl 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])[H] 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- LBMGSGLAWRZARD-UHFFFAOYSA-N 1-ethenylsulfanylbutane Chemical compound CCCCSC=C LBMGSGLAWRZARD-UHFFFAOYSA-N 0.000 description 1
- UDBDWPDPRBGTBD-UHFFFAOYSA-N 1-ethenylsulfanyltetradecane Chemical compound CCCCCCCCCCCCCCSC=C UDBDWPDPRBGTBD-UHFFFAOYSA-N 0.000 description 1
- FJWCOZSXTWZAIP-UHFFFAOYSA-N 1-ethylsulfinylethanol Chemical compound C(C)S(=O)C(C)O FJWCOZSXTWZAIP-UHFFFAOYSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- DJKKWVGWYCKUFC-UHFFFAOYSA-N 2-butoxyethyl 2-methylprop-2-enoate Chemical compound CCCCOCCOC(=O)C(C)=C DJKKWVGWYCKUFC-UHFFFAOYSA-N 0.000 description 1
- WLEXMGAKQNCGQA-UHFFFAOYSA-N 2-dodecoxyethyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOCCOC(=O)C(C)=C WLEXMGAKQNCGQA-UHFFFAOYSA-N 0.000 description 1
- JDGDTSGAXRRXFI-UHFFFAOYSA-N 2-dodecylsulfanylethyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCSCCOC(=O)C(C)=C JDGDTSGAXRRXFI-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- RESVLBLYGGVJPT-UHFFFAOYSA-N 4-O-butyl 1-O-octadecyl 2-methylidenebutanedioate Chemical compound C(C(=C)CC(=O)OCCCC)(=O)OCCCCCCCCCCCCCCCCCC RESVLBLYGGVJPT-UHFFFAOYSA-N 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FYABMGZBIRRBQY-UHFFFAOYSA-N benzene;hydrogen peroxide Chemical compound OO.C1=CC=CC=C1 FYABMGZBIRRBQY-UHFFFAOYSA-N 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- WILBZOKCISUVDL-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 WILBZOKCISUVDL-UHFFFAOYSA-M 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CGNRQCGWXXLTIA-UHFFFAOYSA-N bis(2-ethylhexyl) 2-methylidenebutanedioate Chemical compound CCCCC(CC)COC(=O)CC(=C)C(=O)OCC(CC)CCCC CGNRQCGWXXLTIA-UHFFFAOYSA-N 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- AIDQOWOCUYDWFA-UHFFFAOYSA-M cyclohexyl-dodecyl-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C1CCCCC1 AIDQOWOCUYDWFA-UHFFFAOYSA-M 0.000 description 1
- 239000010727 cylinder oil Substances 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 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
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- OGVXYCDTRMDYOG-UHFFFAOYSA-N dibutyl 2-methylidenebutanedioate Chemical compound CCCCOC(=O)CC(=C)C(=O)OCCCC OGVXYCDTRMDYOG-UHFFFAOYSA-N 0.000 description 1
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 description 1
- HEJZJSIRBLOWPD-WCWDXBQESA-N didodecyl (e)-but-2-enedioate Chemical compound CCCCCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCCCCC HEJZJSIRBLOWPD-WCWDXBQESA-N 0.000 description 1
- DLBIZQBMDGOEFK-UHFFFAOYSA-N didodecyl 2-methylidenebutanedioate Chemical compound CCCCCCCCCCCCOC(=O)CC(=C)C(=O)OCCCCCCCCCCCC DLBIZQBMDGOEFK-UHFFFAOYSA-N 0.000 description 1
- NTROWUKRRAQTAZ-UHFFFAOYSA-N dihexadecyl 2-methylidenebutanedioate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CC(=C)C(=O)OCCCCCCCCCCCCCCCC NTROWUKRRAQTAZ-UHFFFAOYSA-N 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000000975 dye Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- QBDADGJLZNIRFQ-UHFFFAOYSA-N ethenyl octanoate Chemical compound CCCCCCCC(=O)OC=C QBDADGJLZNIRFQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 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
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- OIUCPPFBFOLPIO-UHFFFAOYSA-N tetratriacontyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCOC(=O)C(C)=C OIUCPPFBFOLPIO-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
- C10M151/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F28/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
- C09D133/12—Homopolymers or copolymers of methyl methacrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2462—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds
- C10L1/2468—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds obtained by reactions involving only carbon to carbon unsaturated bonds; derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- 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
- C10M2203/102—Aliphatic fractions
-
- 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
-
- 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
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
- C10M2223/041—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
- 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
- C10M2223/042—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
- C10M2223/045—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
- 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
- C10M2227/02—Esters of silicic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol-fuelled engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
-
- 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—Semi-solids; greasy
-
- 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
Definitions
- This invention deals with novel oil-soluble polymers and lubricating and fuel compositions containing them.
- this invention concerns oil-soluble polymers and compositions containing them wherein said polymers contain at least 0.5% and up to about 60% by Weight of a sulfoxide-containing monomer containing the group where R is an alkyleneoxy group of 2 to 5 carbon atoms or a mixture of these alkyleneoxy groups,
- R" is an alkyl group of 1 to 18 carbon atoms
- X is hydrogen or methyl
- n is an integer having a value of 1 to 50.
- the valuable polymers of the present invention act as dispersants, pour-point depressants, anti-corrosion agents, viscosity-index improvers, or in any two or more of these capacities simultaneously when incorporated in a suitable petroleum product wherein said polymers constitute at least 0.001% of the total weight of the composition.
- Said polymers are particularly valuable as sludge dispersants when incorporated in a lubricating oil to be used in the crankcase of a spark ignition engine.
- deposits form on engine surfaces due to a variety of reasons. While certain additives, especially metal containing salts, and the oil itself have contributed to the formation of deposits on engine surfaces, the major sources of such deposits consist of the various aldehydes, acids, oxy-acids and other similarly reactive, partially-oxidized combustion products of the fuel. Many of these combustion products are carried into the crankcase of the engine along with other blow-by gases. These products are generally insoluble or only partially soluble in oil and, therefore, they tend to sepa rate from the oil and adhere to engine surfaces. In any event, under the elevated temperature conditions prevailing in the engine, these oxidation products quickly polymerize to form solid masses which readily deposit out on the engine surfaces.
- the oil additives used to counteract these problems are generally known as detergents or dispersants.
- the desirable characteristics of a detergent or dispersant are that it be capable of solubilizing or emulsifying in the lubricant, in which it is incorporated, large amounts of all the Various partial oxidation products of the fuel which might -be carried into the oil and also the ability to maintain in suspension in the oil the various solid polymeric materials, which are present therein.
- such detergent or dispersant should be capable of being mixed with various other additives which might be used in any particular lubricating composition.
- such detergent or dispersant should be free of metals so as not to be a source of engine deposits in itself. It is also quite important that a detergent or dispersant be capable of rendering its detergent or dispersant characteristics over an extended period of time.
- the polymers of the present invention possess the enumerated characteristics to a high degree and, therefore, they prove to be extremely useful additives for lubricating compositions. They are particularly valuable when incorporated in lubricating compositions which are to be used in internal combustion engines requiring a lubricant which will permit the engine to be operated at a high level of efliciency over long periods of time.
- the polymers of the present invention are free of metals or any other inorganic components which give ash. Therefore, they will not have a tendency to form deposits themselves as a result of decomposition at high temperatures.
- the sulfoxide monomers used in making the polymers of this invention are those of the formula where R is either hydrogen or methyl,
- R is an alkyleneoxy group of 2 to 5 carbon atoms, such R" is an alkyl group of 1 to 18 carbon atoms, preferably 1 to 4 carbon atoms,
- X is hydrogen or methyl
- n is an integer having a value of 1 to 50
- polymers provided by the invention may be homopolymers when the units contain long-chained oleophilic groups, which render the polymer oil-soluble, it is generally preferred to prepare copolymers of the sulfoxide monomers with less expensive comonomer suitable for imparting oil-solubility to the resulting copolymer.
- oil-soluble as employed throughout this specification and the claims, in connection with the polymers of the subject invention, is intended to mean that the polymer in question is soluble in a lubricant or fuel base to the extent of at least 0.001% by Weight. The following may be used as a base:
- a hydrocarbon fuel such as gasoline or kerosene
- a hydrocarbon oil such as diesel fuel, heating oil or lubricating oil
- a synthetic lubricating oil base comprising esters or polyesters
- a hydraulic fluid comprising hydrocarbons and/ or esters.
- comonomers selected in preparing the copolymers of the present invention will, of course, be dictated by many variables, such as the expense involved, their oilsolubility, the sulfoxide monomer with which they are to be copolymerized and others, as will be understood by those skilled in the art.
- comonomers suitable for this invention there may be employed vinyl carboxylates of up to 20 carbon atoms, such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl laurate and vinyl stearate.
- esters of a,fi-monoethylenically unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid or aconitic acid, with an alkanol having from 1 to 24 carbon atoms, benzyl alcohol, an alkyl-substituted benzyl alcohol or phenol.
- an alkanol having from 1 to 24 carbon atoms
- benzyl alcohol an alkyl-substituted benzyl alcohol or phenol.
- a saturated aliphatic alcohol having from 4 to 18 carbon atoms is employed.
- aralkyl alcohols such as benzyl alcohol or an alkyl-substituted benzyl alcohol, such as dodecylbenzyl alcohol, are also quite useful.
- the choice of the comonomer may range from a relatively low molecular weight comonomer, such as methyl acrylate or methacrylate or ethyl acrylate or methacrylate, to an ester having longer chain groups in the alcohol moiety, such as butyl, vamyl, hexyl or cyclohexyl, up to the long-chained alkyl ester having from 8 to 18 or even 24 carbon atoms, which are generally preferred, such as n-octyl, 2-ethylhexyl, t-octyl, decyl, dodecyl, tridecyl, myristyl, cetyl, hexadecyl, octadecyl, eicosyl or docosyl.
- a relatively low molecular weight comonomer such as methyl acrylate or methacrylate or ethyl acrylate or methacrylate
- the comonomer component of the copolymers may advantageously include a mixture of these various ester monomers.
- the mixtures include such commercial mixtures as those obtained by esteri-fying methacrylic acid or acrylic acid with a mixed alcohol, such as a mixture of about 70% lauryl alcohol with about 30% of myristyl alcohol.
- thioesters obtained from any of the unsaturated acids mentioned and a C to C mercaptan, preferably a C to C mercaptan.
- Typical comonomers which can be worked into the copolymers of this invention in substantial amount include acrylonitrile, vinylidene chloride, styrene, vinyltoluene, a-methylstyrene, dimethyl itaconate, dibutyl itaconate, dioctyl itaconate, didodecyl itaconate, dicetyl itaconate, octadecyl butyl itaconate, didodecyl fumarate, vinyl octanoate, vinyl dodecyl ether, vinyl tetradecyl thioether, vinyl butyl thioether, butoxyethyl methacrylate, dodecyloxyethyl methacrylate and dodecylthioethyl methacrylate.
- the copolymers may contain substantial amounts up to 10 or 15% by weight of nitrogen-containing comonomers, such as vinyl pyrrolidinones, especially N-vinyl-Z-pyrrolidone, N-vinyl piperidinone, a vinyl caprolactam, dimethylaminoethyl acrylate or methacrylate, N (dimethylaminoethyl)acrylamide or N,N dimethylmethacrylamide, N-vinyl succinimide or vinyl pyridines.
- nitrogen-containing comonomers such as vinyl pyrrolidinones, especially N-vinyl-Z-pyrrolidone, N-vinyl piperidinone, a vinyl caprolactam, dimethylaminoethyl acrylate or methacrylate, N (dimethylaminoethyl)acrylamide or N,N dimethylmethacrylamide, N-vinyl succinimide or vinyl pyridines.
- the sulfoxide monomers used in forming the polymers of the present invention may be prepared in any suitable manner.
- One such manner comprises the oxidation of the sulfide atom of corresponding sulfides containing the group or groups in place of the hydrogen of the carboxyl group of acrylic or methacrylic acid or in place of one or more of the hydrogen atoms of the carboxyl groups of maleic, fumaric,
- the polymers of the present invention may be produced by polymerizing or copolymerizing the sulfoxide monomers, such as in bulk or in solution.
- Solution polymerization may be effected in any suitable solvent for the product obtained which, in the case of some of the monomers containing oxyalkylene groups, include Water, ethanol, or acetone, and in the case of the other monomers, may include benzene, toluene, xylenes, kerosene, gasoline, aromatic naphthas, chlorinated hydrocarbons, such as ethylene dichloride, dimethylformamide, esters such as butyl acetate or ethyl propionate, or any of the ester or hydrocarbon liquids within which the polymers are to be used.
- the solvent may be retained in the final polymer or may be stripped off. It is usually desirable to displace from the final polymer a volatile solvent with a good quality oil, such as SUS- or neutral oil to give an oil solution of the final polymer.
- a relatively non-volatile organic liquid such as dibutyl sebacate, dioctyl sebacate, dioctyl azeleate, tributyl phosphate, ltricresyl phosphate, dibutylphenyl phosphate, silicate esters, or silicone fluids. It may be desirable to use such liquids as solvent when the final polymer is to be used in liquids of this sort.
- the polymer may be transferred to the oil or relatively non-volatile ester or the like by mixing the solution of polymer and oil or ester and distilling off the volatile solvent. Such mixtures may be heated to 100 to 200 C. at reduced pressures to ensure complete removal of the volatile solvent. During the heating of the mixture, remaining traces of initiator are decomposed.
- the polymerization may be effected with the aid of a free-radical initiator or catalyst, such as an organic or inorganic peroxidic catalyst, including peroxides and persulfates, and the azo catalysts.
- a free-radical initiator or catalyst such as an organic or inorganic peroxidic catalyst, including peroxides and persulfates, and the azo catalysts.
- a free-radical initiator or catalyst such as an organic or inorganic peroxidic catalyst, including peroxides and persulfates, and the azo catalysts.
- organic peroxidic catalysts examples include, 2,2-bis-(t-butylperoxy)butane, benzoyl peroxide, methyl ethyl ketone peroxide, acetyl peroxide, caproyl peroxide, lauroyl peroxide, butyl perbenzoate, butyl hydroperoxide, cumene hydroperoxide, pmenthane hydroperoxide, diisopropylbenzene hydroperoxide and other t-alkyl hydroperoxides. Quaternary ammonium activators may be used and are especially valuable with the hydroperoxides.
- a particularly effective initiator system is developed by using a hydroperoxide together with a quaternary ammonium salt, such as tetra methylammonium chloride, benzyltrimethylammonium chloride, diisobutylphenoxyethoxyethyldimethylbenzylammonium chloride, lauryldirnethylbenzylammonium chloride, lauryldimethylcyclohexylammonium chloride, dodecylbenzyltrimethylammonium bromide, didodecenyldimethylammonium chloride, cetyltrimethylammonium chloride, cetylpyridinium chloride, or other quaternary ammonium salts which have alkyl, alkenyl, cycloalkyl or aralkyl groups as N-substituents.
- a quaternary ammonium salt such as tetra methylammonium chloride, benzyltrimethylammonium chloride,
- the quaternary ammonium salt may be used in a proportion from about 0.01 to 0.5% of the weight of the polymerizing mixture or preferably from 5 to about 40% of the hyd-roperoxide Weight.
- the salt acts as an activator and helps to control molecular sizes of the polymer as well as speeding up the rate of polymerization.
- azo catalysts include azodiisobutyronitrile, azodiisobutyramide, dimethyl or diethyl or dibutyl azodiisobutyrate, azobis-(a, -dimethylvaleronitrile, azobis- (ocmethylbutyronitrile azobisa-methylvaleronitrile dimethyl or diethyl azobismethylvalerate and the like.
- Polmerization may also be initiated by high-energy irradiation.
- Suitable sources of high-energy irradiation are radioactive materials and electron accelerators.
- Useful as radioactive materials that supply gamma rays are irradiated isotopes, such as Co fission products, such as Cs adjuncts to fission reactants, such as radioactive xenon, and the like.
- a C0 source is particularly effec tive.
- Useful as radioactive materials that supply beta rays are Sr and the like.
- Valuable as electron accelerators, which supply beta rays, are the Van de Graaif generator, the resonant transformer, and the like.
- the copolymers provided by the present invention may be prepared by copolymerizing in the manner described above one or more monoethylenically unsaturated polymerizable monomers, which are such as to result in a copolymer which is oil-soluble and which contains 0.5 to about 60% or more by weight of at least one of the sulfoxide monomers of the present invention with one or more of the comonomers previously described.
- polymerizable monoethylenically un saturated monomer denotes a compound which contains the vinylene group
- p represents the whole number 1 or 2, and which compounds are homopolymerizable and copolymerizable and also those that are only copolymerizable.
- the polymers of the present invention may be added to the liquid hydrocarbon or ester base in proportions of about 0.001% up to 25% by weight based on the total Weight of the composition wherein it serves the purpose of imparting improved properties as enumerated heretofore.
- Such compositions are employed as lubricants, including line, kerosene, diesel oil, jet engine fuels and hydraulic transmission oils.
- a lubricating oil composition wherein the polymer is incorporated to serve as a sludge dispersant, about 0.1 to about 10% by weight of polymer need be added in order to be eflfective.
- the proportion of polymer may be in the range of 0.001 to about 1%. More or less than the specified limits of the polymer may be employed in any particular case. However, if more is used, it is generally found to be an unnecessary expense and if less than the lower limit specified is employed, the extent of the effect is generally diminished proportionately.
- hydrocarbon oils referred to throughout this specification may be of a lubricating or fuel type and their composition may constitute paraflinic, naphthenic or aromatic components or any mixtures thereof.
- ester liquids referred to throughout this specification include fatty acid esters of higher alcohols, such as the esters of alcohols from octyl to octadecyl with fatty acids of 1 to 18 or more carbon atoms, and preferably 4 to 18 carbon atoms.
- Ester liquids may also be diesters of aliphatic dicarboxylic acids, such as the diesters formed from diacids having from 6 to 12 carbon atoms with monohydric alcohols having from 4 to 12 carbon atoms and preferably 6 to 10 carbon atoms, or from mixtures of such alcohols. These include the sebacates, azeleates and the like.
- polymers of the present invention may be incorporated in hydrocarbon or liquid ester compositions, in conventional ways wherein other additives are employed, such as anti-oxidants, stabilizers, wear-resisting agents, other detergents, anti-rust agents, pour-point depressants, viscosity-index improvers, anti-foaming agents or dyes.
- additives such as anti-oxidants, stabilizers, wear-resisting agents, other detergents, anti-rust agents, pour-point depressants, viscosity-index improvers, anti-foaming agents or dyes.
- the solution obtained when polymerization is effected in a solvent or an oil can be used as a concentrate for addition to the oil to be modified therewith.
- a concentrate obtained in this manner may conveniently contain up to as much as 70% polymer by weight.
- the asphaltenes are obtained by oxidizing a naphthenic oil with air under the influence of a trace of iron salt as catalyst, such as ferric naphthenate.
- the oxidation is desirably accomplished at 175 C. for 72 hours by passing a stream of air through a naphthenic oil.
- Pentane is added to the cooled, oxidized oil to form a sludge which may be separated by centrifuging.
- the sludge is freed from oil by extracting it with pentane. It is then taken up wit-h chloroform and the resulting solution is adjusted to a solids content of about 2% (wt. per vol.).
- Blends may be prepared to contain percentages varying from about 2 to 0.01% or even lower of polymer in oil.
- a 10 ml. sample of a blend is treated with 2 ml. of the standard solution of asphaltenes in chloroform.
- the sample and reagent are thoroughly mixed in a test tube and the tube is placed in a forced draft oven at C. for 2 hours to drive off volatile material. The tube is then allowed to cool and the appearance of the sample is noted.
- the oil will appear clear although colored. The appearance may then vary from being hazy or turbid to the state in which suspended particles appear, and finally to the point where the asphaltenes appear in a flocculent state. The polymers are rated accordingly.
- API SERVICE MS SEQUENCE V-A TEST This test evaluates the sludge dispersant characteristics of a lubricant under low and medium temperature operating conditions.
- a single cylinder oil test engine is operated under conditions described in ASTM Special Technical Publication No. 315, published by the American Society for Testing Materials, 1916 Race St., Philadelphia, Pa. 19103.
- the engine may be rated at any time during the course of the test.
- Example 1 A 500 cc. round bottom 3-neck flask is equipped with a gas inlet tube, a condenser, a circular-type glass stirrer and an addition funnel. The system is flushed with nitrogen and the bath surrounding the reaction vessel is maintained at 90 C.
- reaction vessel There is added to the reaction vessel a mixture consisting of 93.5 parts of lauryl-myristyl methacrylate (96.3% purity by gas-liquid-chromatography (GLC), representing 90.0 parts of 100% monomer), 10.0 parts of ethylsulfinylpolyethoxyethyl methacrylate (100% purity assumed, containing 6.28 ethoxy units), 50.0 parts of toluene, 1.6 parts of azobisisobutyronitrile (12.5% solution in chloroform) and 0.3 part n-dodecyl mercaptan.
- LPC gas-liquid-chromatography
- the resulting solution is 39.1% polymer, as determined by precipitation, representing a polymer yield of 96.3%. Sulfur analysis on the precipitated polymer reveals that a quantitative conversion of the sulfur-containing monomer has been achieved.
- the polymer is stripped into 100 viscosity neutral oil to give a 29.3% solution with a viscosity of 106.8 cs. at' 210 F.
- Six-hundred and twenty-five ten thousandths percent of this copolymer in an oil test blend disperses 0.4% asphaltenes at 150 C.
- the copolymer of Example 1 is incorporated at a level of 1% by weight in a neutral oil containing 1% zinc dialkyldithiophosphate.
- a copolymer of n-alkylpolyethylene oxide methacrylate such as described in United States Patent No. 2,892,783.
- composition A lubricating composition A
- Composition B lubricating composition B
- the copolymer of Example 1 is an excellent dispersant in a lubricating oil which retains its dispersant characteristics over an extended period of time. This fact is emphatically evidensed by the comparison of the performance of Com position A with that of Composition B. Bearing in mind that a 70.0 rating is equivalent to clean, a 56.0 rating is not reached until 165 hours has elapsed where Composition A is used, whereas the same rating is achieved at 143 hours with Composition B.
- the ability of the present invention to retain its dispersant characteristics over greater lengths of time is more fully demonstrated by the fact that a 49.0 rating is not obtained until 199 hours of running time where Composition A is used. However, the 49.0 rating is reached only 5 hours of running time after the 56.0 rating is reached where Composition B is used. This, of course, indicated that Composition B has, 'more or less, lost its dispersant ability.
- Example 2 Apparatus is provided with an efficient stirrer, a thermometer, inlet and outlet tubes for gas and a device for admitting reactants.
- the polymerization vessel is heated with an electrically heated oil bath and the apparatus is swept with nitrogen throughout the polymerization cycle.
- AIBN azodiisobutyronitrile
- the resulting clear viscous solution analyzes 39.2% of solids as copolymer by precipitation,
- the solid copolymer contains 1.01% sulfur representing 14.6% of ethylsulfinylpolyethoxyethyl methacrylate in the copolymer.
- a portion of the toluene solution of this copolymer is mixed with 100 SUS neutral oil and heated and stirred under reduced pressure to C. at 10 mm. to remove the volatile matter.
- the resulting oil solution, 29.4% of copolymer shows a viscosity of 77.8 cs. at 210 F.
- An oil blend made up to contain 2.06% of said copolymer in a base oil shows viscosities of 7.20 cs. at 210 F. and 44.16 cs. at 100 F., representing a viscosity index of 129.
- the viscosity of the base oil is 5.56 cs. at 210 F. and 35.46 cs. at 100 F., with a viscosity index of 103.3.
- Example 3 In a manner similar to that described in Example 2, there are copolymerized:
- copolymer This charge is allowed to copolymerize under nitrogen at 89 to 93 C. during 6% hours total heating time; 12 incremental additions of 0.1 part of AIBN in 0.7 part of chloroform are added every 30 minutes beginning 45 minutes after the heating is started. The batch is finally diluted with 85 parts of toluene. The solids found as copolymer is 38.2%. This copolymer shows 1.08% sulfur representing 10.9% of ethylsulfinylpolyet-hoxyethyl methacrylate in the copolymer.
- copolymer is transferred to 100 SUS neutral oil on stirring and heating a portion of the toluene solution of the copolymer with the oil to 125 C./ mm. This results in an oil solution consisting of 29.4% of copolymer.
- its viscosity is 107.9 cs.
- An oil blend is made up using this concentrate to make the blend 3.94% of copolymer.
- the base oil used has a viscosity of 5.56 cs. at 210 F. and 35.46 cs. at 100 F., with a viscosity index of 103.3.
- the viscosity of the blend is 9.42 cs. at 210 F. and 56.41 cs. at 100 F., with a viscosity index of 139.
- Example 4 Using the apparatus described in Example 2, a monomeric mixture is made up of:
- Example 5 In another run, performed in a manner similar to the procedure described in Example 4, except that more toluene is used, there are allowed to copolymerize:
- toluene Twenty parts of toluene is added during the course of introducing this monomeric mixture to the polymerization vessel. Incremental additions of the hydroperoxide solution (50% active ingredient), of the 25% solution of quaternary ammonium chloride in n-hex-anol, of n-dodecyl mercaptan and of toluene added during the course of the copolymerization totals 0.25, 0.05, 0.15 and 12.5 parts, respectively. At 360 minutes, the batch is diluted to 37% of copolymer on the basis of the theoretical yield using 25.3 parts of toluene.
- Example 6 Dilauryl-myristyl fumarate is prepared from a mixture consisting of 2% of n-decanol, 71% of n-dodecanol, 27% of n-tetradecanol and 1% of n-hexadecanol using direct esterifiaction of fumaric acid with p-toluene sulfonic acid as catalyst.
- the diester is obtained as a stripped residue which analyzes 0.03% ash.
- the acid number is 0 and the saponification number is 223.
- a mixture composed of 71 parts of the dilauryl-myristyl fumarate, 24 parts of vinyl acetate, 5 parts of ethylsulfinyl(ethoxy) ethyl methacrylate, 2 parts of toluene and 1 part of t-butyl perbenzoate is heated at 100 C. and stirred under a nitrogen atmosphere for 2 hours. At 3 hours, 5 hours and 8 hours, 0.4 part of t-butyl perbenzoate in 5 parts of toluene is added and the temperature is kept at 100 to C. for a total of 16 hours. At 16 hours, 33 parts of toluene is added. The toluene solution which results is viscous and analyzes 57.3% solids as copolymer.
- This copolymer is tested for dispersing action of asphaltenes in oil and found to be effective even at 0.125 of copolymer.
- Example 7 Dilauryl-myristyl itaconate is prepared in a manner similar to that described in Example 6.
- the hydroxyl number on the mixed C C alcohol is used to calculate the theoretical saponification number of 225.6 for the diester.
- the saponification number found is 227.5.
- the alcohol mixture contains 71% of n-dodecanol.
- a mixture is prepared from 47.5 parts of dilaurylmyristyl itaconate and 2.5 parts of ethylsulfinyl(ethoxy) ethyl methacrylate.
- Five parts of toluene, parts of diisopropylbenzene hydroperoxide, 50% strength as the hydroperoxide and 1 part of a 25% solution of didodecenyldimethylammonium chloride in n-butanol are added to the polymerization vessel with the monomers. copolymerization ensued at a batch temperature of 110 to 115 C.
- Additional hydroperoxide (50% solution), quaternary ammonium chloride (25 solution) and toluene are added as follows: at 3 hours, 1 part hydroperoxide solution, 0.2 part didodecenyldimethylammonium chloride solution with 2.5 parts of toluene; at 4 hours, 1.5 parts of hydroperoxide solution, 0.3 part of di-docenyldimethylammonium chloride solution; at 5, 6 and 7 hours, 1 part hydroperoxide solution, 0.2 parts didodecenyldimethylammonium chloride solution with 2.5 parts of tolu: ene, respectively. At 8 hours, the batch is diluted with 6 parts of toluene. A solution consisting of 55% copolymer is the product.
- Example 8 Using the apparatus described in Example 1, there is fed into the polymerization vessel during 120 minutes, the following mixture:
- An oil blend is prepared containing 2% of this copolymer. It eiiectively disperses 0.4% asphaltenes in the standard asphaltenes test at 150 C.
- Example 9 In another copolymerization carried out according to the procedure given for Example 2, there are allowed to copolymerize:
- cetyl-stearyl methacrylate 18 parts of cetyl-stearyl methacrylate, the methacrylic ester having been prepared from a commercial alcohol composed of 2% tetradecanol, 68% of octadecanol and 30% of hexadecanol,
- Example 2 The same copolymerization conditions are followed, as indicated in Example 2, using mercaptan and toluene, with azodiisobutyronitrile as the catalyst.
- the clear viscous solution analyzes 39.5% of solids as copolymer.
- This copolymer is'an eifective dispersant. Only 0.5% of copolymer in a test blend disperses 0.4% of asphaltenes at 150 C.
- a mixture of 14.5 parts of the 39.5% solution and 20.6 parts of tributyl phosphate is stirred and heated to 100 to 105 C. at 10 mm. for 60 minutes to give a 20% solution of copolymer in the tributyl phosphate.
- This concentrate is useful in preparing hydraulic fluids where a phosphate is desirable.
- copolymers are also useful in synthetic lubricants.
- 14.5 parts of the above toluene solution of copolymer is mixed with 17.9 parts of di-Z-ethylhexyl sebacate and heated and stirred, as above, to give 25.4 parts of a dispersant-type synthetic lubricant.
- Example 10 The procedure of Example 4 is used with a starting mixture of 40.1 parts of lauryl-myristyl methacrylate, 6 parts of styrene, 2.5 parts of toluene, 0.2 part of a 50% solution of diisopropylbenzene 'hydroperoxide and 0.04 part of 25% solution of t-octylphenoxyethoxyethylbenzyldlmethylammonium chloride monohydrate.
- Increments are supplied of a 50% solution of diisopropylbenzene hydroperoxide, of a 5% solution of t-octylphenoxyethoxyethylbenzyldimethylammonium chloride monohydrate and toluene to totals of 0.22, 0.22 and 12.5 parts, respectively. Heating is discontinued at 6.25 hours. Then, 39 parts of toluene is added and the batch is allowed to cool to 30 C. with stirring. The resulting toluene solution contains by analysis, 43.2% of polymer. A toluene solution adjusted to 30% of polymer has a viscosity of 200 cs. at F.
- Example 11 In the same manner as in the preceding example, there is allowed to copolymerize 40.1 parts of lauryl-myristyl methacrylate with 4 parts of styrene.
- 4.5 parts of ethylsulfinyl(ethoxy) ethyl methacrylate is mixed with 2 parts of N-vinyl-2-pyrrolidinone, parts of toluene, 0.025 part of a 50% solution of diisopropylbenzene hydroperoxide and 0.025 part of a 5% solution of t-octylphenoxyethoxyethylbenzyldimethylammonium chloride monohydrate.
- the resulting toluene solution contains 44% copolymer.
- this copolymer is used in a test blend, only 0.125% is required to disperse 0.4% asphaltenes at 150 C.
- Example 12 A copolymerization similar to that of Example 4 was carried out using ethylsulfinylethovy(propoxy) 3,01 propyl methacrylate in place of the ethylsulfinyl(eth-oxy) ethyl methacrylate.
- the ethylsulfinylethoxy(propoxy) propyl methacrylate was obtained by reacting ethylsulfinylethanol with propylene oxide. Excellent dispersant ability was exhibited by the resulting copolymer.
- a viscous liquid to solid polymer of monoethylenically unsaturated polymerizable monomers comprising (a) about 0.5 to 60% by weight of a sulfoxide-containing monomer of the formula R is hydrogen or methyl, R is an alkeneoxy group of 2 to 5 carbon atoms, n is an integer having a value of 1 to 50, X is hydrogen or methyl, R" is an alkyl of 1 to 18 carbon atoms and (b) about 40 to 99.5% by weight of at least one ester of an (1) u,B-monoethylenically unsaturated polymerizable carboxylic acid and an alkanol having from 1 to 24 carbon atoms, benzyl alcohol, an alkyl-substituted benzyl alcohol or phenol or a (2) vinyl carboxylate of up to about 20 carbon atoms, said polymer being oil-soluble.
- R is an alkyleneoxy group of 2 to 5 carbon atoms
- n is an integer having a value of 1 to 50
- X is hydrogen or methyl
- R" is an alkyl of 1 to 18 carbon atoms and 12.
- a composition according to claim 9 wherein said liquid ester is di-Z-ethylhexyl sebacate.
- composition according to claim 9 wherein said (a) is ethylsulfinylpolyethoxyethyl methacrylate or ethylsulfinylpolyethoxyethyl acrylate.
- composition according to claim 9 wherein said (b) is an ester of acrylic or methacrylic acid with a mixture of about 70% lauryl alcohol and about 30% myristyl alcohol.
- composition according to claim 9 wherein said (a) is ethylsulfinylpolyethoxyethyl. methacrylate and said b) is lauryl-myristyl methacrylate.
- composition according to claim 9 wherein said (a) is ethylsulfinylpolyethoxyethyl acrylate and said (b) is a mixture of vinyl stearate and vinyl acetate.
- composition according to claim 9 wherein said (a) is ethylsulfinylethoxy polypropoxypropyl methacrylate and said (b) is lauryl-myristyl methacrylate.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US539633A US3337458A (en) | 1965-12-23 | 1966-04-04 | Oil-soluble polymers and compositions containing them |
BE687566D BE687566A (xx) | 1965-12-23 | 1966-09-29 | |
FR78198A FR1494694A (fr) | 1965-12-23 | 1966-09-29 | Polymères solubles dans les huiles et compositions lubrifiantes et combustibles en contenant |
NL6615838A NL6615838A (xx) | 1965-12-23 | 1966-11-09 | |
ES334382A ES334382A1 (es) | 1965-12-23 | 1966-12-10 | Metodo para preparar una composicion adecuada para su uso como dispersante. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US51613765A | 1965-12-23 | 1965-12-23 | |
US539633A US3337458A (en) | 1965-12-23 | 1966-04-04 | Oil-soluble polymers and compositions containing them |
Publications (1)
Publication Number | Publication Date |
---|---|
US3337458A true US3337458A (en) | 1967-08-22 |
Family
ID=27058727
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US539633A Expired - Lifetime US3337458A (en) | 1965-12-23 | 1966-04-04 | Oil-soluble polymers and compositions containing them |
Country Status (4)
Country | Link |
---|---|
US (1) | US3337458A (xx) |
BE (1) | BE687566A (xx) |
ES (1) | ES334382A1 (xx) |
NL (1) | NL6615838A (xx) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3485755A (en) * | 1967-09-11 | 1969-12-23 | Union Carbide Corp | Lubricating compositions including a polymer which contains an ammonium sulfate salt |
US4707516A (en) * | 1985-08-09 | 1987-11-17 | Ceskoslovenskla Akademie Ved | Polymeric sulfoxide based on the polymer of vinylalcohol |
US4759908A (en) * | 1986-10-03 | 1988-07-26 | Texaco Inc. | Polythioether corrosion inhibition system |
US9493600B2 (en) | 2011-08-10 | 2016-11-15 | Jsr Corporation | Polymer, surface hydrophilizing agent containing said polymer, and manufacturing method for substrate having hydrophilic surface |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3053806A (en) * | 1960-12-29 | 1962-09-11 | Union Carbide Corp | Acrylonitrile- and vinyl chloride-containing polymers and fibrous articles thereof |
US3100748A (en) * | 1959-11-10 | 1963-08-13 | Shell Oil Co | Lubricating compositions |
US3102863A (en) * | 1959-06-15 | 1963-09-03 | Shell Oil Co | Lubricating compositions |
US3206400A (en) * | 1960-10-10 | 1965-09-14 | Shell Oil Co | Mineral oil composition |
-
1966
- 1966-04-04 US US539633A patent/US3337458A/en not_active Expired - Lifetime
- 1966-09-29 BE BE687566D patent/BE687566A/xx unknown
- 1966-11-09 NL NL6615838A patent/NL6615838A/xx unknown
- 1966-12-10 ES ES334382A patent/ES334382A1/es not_active Expired
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3102863A (en) * | 1959-06-15 | 1963-09-03 | Shell Oil Co | Lubricating compositions |
US3100748A (en) * | 1959-11-10 | 1963-08-13 | Shell Oil Co | Lubricating compositions |
US3206400A (en) * | 1960-10-10 | 1965-09-14 | Shell Oil Co | Mineral oil composition |
US3053806A (en) * | 1960-12-29 | 1962-09-11 | Union Carbide Corp | Acrylonitrile- and vinyl chloride-containing polymers and fibrous articles thereof |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3485755A (en) * | 1967-09-11 | 1969-12-23 | Union Carbide Corp | Lubricating compositions including a polymer which contains an ammonium sulfate salt |
US4707516A (en) * | 1985-08-09 | 1987-11-17 | Ceskoslovenskla Akademie Ved | Polymeric sulfoxide based on the polymer of vinylalcohol |
US4759908A (en) * | 1986-10-03 | 1988-07-26 | Texaco Inc. | Polythioether corrosion inhibition system |
US9493600B2 (en) | 2011-08-10 | 2016-11-15 | Jsr Corporation | Polymer, surface hydrophilizing agent containing said polymer, and manufacturing method for substrate having hydrophilic surface |
TWI561544B (xx) * | 2011-08-10 | 2016-12-11 | Jsr Corp |
Also Published As
Publication number | Publication date |
---|---|
ES334382A1 (es) | 1968-03-16 |
BE687566A (xx) | 1967-03-29 |
NL6615838A (xx) | 1967-06-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3501405A (en) | Lubricating and fuel compositions comprising copolymers of n-substituted formamide-containing unsaturated esters | |
US3506574A (en) | Lubricating oils and fuels containing graft copolymers | |
US3052648A (en) | Preparation of copolymers useful as dispersants in oils | |
US3311558A (en) | N-alkylmorpholinone esters of alkenylsuccinic anhydrides | |
US3073807A (en) | Copolymers of olefins with sulfonyloxy compounds | |
US4021357A (en) | Multifunctional tetrapolymer lube oil additive | |
US3304260A (en) | Compositions of improved viscosity index containing alkyl polymethacrylate of high relative syndiotacticity | |
US3142664A (en) | Oil soluble copolymer of a nu-vinyl pyrrolidinone and an alkyl ester of an unsaturated monocarboxylic acid | |
US3634493A (en) | Oil-soluble azo compounds | |
US2892786A (en) | Lubricant composition | |
US3371040A (en) | Lubricant and fuel compositions | |
US3311559A (en) | Oil additive | |
US3244631A (en) | Lubricating composition containing non-ash forming additives | |
US3087893A (en) | Copolymers of maleic anhydride and unsaturated esters as additives in oils | |
US3147222A (en) | Compositions comprising a petroleum liquid and an nu-vinyl pyrrolidinaone polymer | |
US3232876A (en) | Boron-containing copolymers and lubricating oils containing them | |
US3238133A (en) | Lubricating oil compositions containing neutral ashless polymeric detergents | |
US3337458A (en) | Oil-soluble polymers and compositions containing them | |
US3293182A (en) | Fuel and lubricant compositions | |
US4036766A (en) | Polymethacrylate additives and lube compositions thereof | |
US3637610A (en) | Multifunctional polymeric additive | |
US2892816A (en) | Detergent copolymers | |
US3001942A (en) | Lubricant composition | |
CA2057492C (en) | Multifunctional additive for lubricating oils | |
US2892788A (en) | Lubricant composition |