CA1134090A - Non-cross linked products of hydrocarbon polymers with olefinic polar compounds and processes for making same - Google Patents

Non-cross linked products of hydrocarbon polymers with olefinic polar compounds and processes for making same

Info

Publication number: CA1134090A
Authority: CA; Canada
Prior art keywords: ethylene; propylene; norbornene; polymer; additive
Prior art date: 1977-07-28
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

Application number

CA304,268A

Other languages

English (en)

French (fr)

Inventor

Donald R. Lachowicz

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

Texaco Development Corp

Original Assignee

Texaco Development Corp

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

1977-07-28

Filing date

1978-05-29

Publication date

1982-10-19

1978-05-29 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1982-10-19 Application granted granted Critical

1982-10-19 Publication of CA1134090A publication Critical patent/CA1134090A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 43
150000001875 compounds Chemical class 0.000 title claims abstract description 40
230000008569 process Effects 0.000 title claims abstract description 25
229920000642 polymer Polymers 0.000 title claims description 61
229930195733 hydrocarbon Natural products 0.000 title claims description 34
150000002430 hydrocarbons Chemical class 0.000 title claims description 34
239000004215 Carbon black (E152) Substances 0.000 title claims description 33
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims abstract description 49
239000000047 product Substances 0.000 claims abstract description 46
239000000203 mixture Substances 0.000 claims abstract description 43
229920001577 copolymer Polymers 0.000 claims abstract description 29
229920001897 terpolymer Polymers 0.000 claims abstract description 29
239000007795 chemical reaction product Substances 0.000 claims abstract description 9
150000001993 dienes Chemical class 0.000 claims abstract description 7
230000001050 lubricating effect Effects 0.000 claims abstract description 5
239000002480 mineral oil Substances 0.000 claims description 36
235000010446 mineral oil Nutrition 0.000 claims description 35
239000000654 additive Substances 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 29
230000000996 additive effect Effects 0.000 claims description 26
239000003921 oil Substances 0.000 claims description 26
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 25
239000003999 initiator Substances 0.000 claims description 23
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 20
-1 polymethylene Polymers 0.000 claims description 20
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
229940063557 methacrylate Drugs 0.000 claims description 12
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
239000011630 iodine Substances 0.000 claims description 11
229910052740 iodine Inorganic materials 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
150000003254 radicals Chemical class 0.000 claims description 10
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 claims description 10
239000010687 lubricating oil Substances 0.000 claims description 9
229920002943 EPDM rubber Polymers 0.000 claims description 8
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000007810 chemical reaction solvent Substances 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
229920000307 polymer substrate Polymers 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
229940095050 propylene Drugs 0.000 claims description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
239000000758 substrate Substances 0.000 claims description 6
OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 claims description 5
KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000004982 aromatic amines Chemical class 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
239000012299 nitrogen atmosphere Substances 0.000 claims description 4
150000002978 peroxides Chemical class 0.000 claims description 4
SSHYVAUGFCDEAP-UHFFFAOYSA-N (2-ethylpyridin-3-yl) prop-2-enoate Chemical compound C(C=C)(=O)OC=1C(=NC=CC1)CC SSHYVAUGFCDEAP-UHFFFAOYSA-N 0.000 claims description 3
PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 claims description 3
RCSKFKICHQAKEZ-UHFFFAOYSA-N 1-ethenylindole Chemical compound C1=CC=C2N(C=C)C=CC2=C1 RCSKFKICHQAKEZ-UHFFFAOYSA-N 0.000 claims description 3
DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 3
KDAKDBASXBEFFK-UHFFFAOYSA-N 2-(tert-butylamino)ethyl prop-2-enoate Chemical compound CC(C)(C)NCCOC(=O)C=C KDAKDBASXBEFFK-UHFFFAOYSA-N 0.000 claims description 3
UGIJCMNGQCUTPI-UHFFFAOYSA-N 2-aminoethyl prop-2-enoate Chemical compound NCCOC(=O)C=C UGIJCMNGQCUTPI-UHFFFAOYSA-N 0.000 claims description 3
XUGNJOCQALIQFG-UHFFFAOYSA-N 2-ethenylquinoline Chemical compound C1=CC=CC2=NC(C=C)=CC=C21 XUGNJOCQALIQFG-UHFFFAOYSA-N 0.000 claims description 3
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 3
CFZDMXAOSDDDRT-UHFFFAOYSA-N 4-ethenylmorpholine Chemical compound C=CN1CCOCC1 CFZDMXAOSDDDRT-UHFFFAOYSA-N 0.000 claims description 3
DZGGGLJOCYPKHN-UHFFFAOYSA-N 4-ethenylquinoline Chemical compound C1=CC=C2C(C=C)=CC=NC2=C1 DZGGGLJOCYPKHN-UHFFFAOYSA-N 0.000 claims description 3
ULKSJUHREFNNEO-UHFFFAOYSA-N [2-(dimethylamino)-2-methylpropyl] prop-2-enoate Chemical compound CN(C)C(C)(C)COC(=O)C=C ULKSJUHREFNNEO-UHFFFAOYSA-N 0.000 claims description 3
238000007259 addition reaction Methods 0.000 claims description 3
FTWHFXMUJQRNBK-UHFFFAOYSA-N alpha-Methylen-gamma-aminobuttersaeure Natural products NCCC(=C)C(O)=O FTWHFXMUJQRNBK-UHFFFAOYSA-N 0.000 claims description 3
239000003879 lubricant additive Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
239000003208 petroleum Substances 0.000 claims description 2
FMAMSYPJXSEYSW-VOTSOKGWSA-N (4e)-hepta-1,4-diene Chemical compound CC\C=C\CC=C FMAMSYPJXSEYSW-VOTSOKGWSA-N 0.000 claims 2
BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims 2
QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 claims 2
CVJFADFTQUIXSG-VQHVLOKHSA-N CCCCCCCC\C=C\CC=C Chemical compound CCCCCCCC\C=C\CC=C CVJFADFTQUIXSG-VQHVLOKHSA-N 0.000 claims 2
VGAJYAOJRBZVNG-UHFFFAOYSA-N [2-(dimethylamino)-2-methylpropyl] 2-methylprop-2-enoate Chemical compound CN(C)C(C)(C)COC(=O)C(C)=C VGAJYAOJRBZVNG-UHFFFAOYSA-N 0.000 claims 2
MPXNNMASLYQCAH-UHFFFAOYSA-N ethene;5-ethylidenebicyclo[2.2.1]hept-2-ene;prop-1-ene Chemical compound C=C.CC=C.C1C2C(=CC)CC1C=C2 MPXNNMASLYQCAH-UHFFFAOYSA-N 0.000 claims 2
ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 claims 2
JCYNVOGKPGMMRV-UHFFFAOYSA-N 5-tetradecylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=CCCCCCCCCCCCCC)CC1C=C2 JCYNVOGKPGMMRV-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 8
239000000243 solution Substances 0.000 description 33
229940042472 mineral oil Drugs 0.000 description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
239000002270 dispersing agent Substances 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 11
229960005419 nitrogen Drugs 0.000 description 11
229920000578 graft copolymer Polymers 0.000 description 7
239000000178 monomer Substances 0.000 description 7
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
239000011575 calcium Substances 0.000 description 6
229910052791 calcium Inorganic materials 0.000 description 6
239000003599 detergent Substances 0.000 description 6
239000000314 lubricant Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
238000001556 precipitation Methods 0.000 description 5
230000008719 thickening Effects 0.000 description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
229940093470 ethylene Drugs 0.000 description 4
238000001914 filtration Methods 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
238000000746 purification Methods 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000002939 deleterious effect Effects 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
239000007789 gas Substances 0.000 description 3
230000006872 improvement Effects 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
150000002642 lithium compounds Chemical class 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
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 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
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PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
229910052788 barium Inorganic materials 0.000 description 2
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000008859 change Effects 0.000 description 2
238000002485 combustion reaction Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
230000006866 deterioration Effects 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000006263 metalation reaction Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000010008 shearing Methods 0.000 description 2
239000010802 sludge Substances 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
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000002966 varnish Substances 0.000 description 2
239000003039 volatile agent Substances 0.000 description 2
HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
IRVGWDJFZXOKDK-FNORWQNLSA-N (3e)-trideca-1,3-diene Chemical compound CCCCCCCCC\C=C\C=C IRVGWDJFZXOKDK-FNORWQNLSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
MBEVSMZJMIQVBG-UHFFFAOYSA-N 2-(hydroxymethyl)guanidine Chemical compound NC(N)=NCO MBEVSMZJMIQVBG-UHFFFAOYSA-N 0.000 description 1
RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
ZWAPMFBHEQZLGK-UHFFFAOYSA-N 5-(dimethylamino)-2-methylidenepentanamide Chemical compound CN(C)CCCC(=C)C(N)=O ZWAPMFBHEQZLGK-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-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
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
240000001987 Pyrus communis Species 0.000 description 1
102100029469 WD repeat and HMG-box DNA-binding protein 1 Human genes 0.000 description 1
101710097421 WD repeat and HMG-box DNA-binding protein 1 Proteins 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001338 aliphatic hydrocarbons 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
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 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
125000003118 aryl group Chemical group 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
230000008901 benefit Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-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
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000012967 coordination catalyst Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000004132 cross linking 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
230000007812 deficiency Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-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
238000001035 drying Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-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
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000005461 lubrication Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
KRPXAHXWPZLBKL-UHFFFAOYSA-L magnesium;diphenoxide Chemical class [Mg+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 KRPXAHXWPZLBKL-UHFFFAOYSA-L 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
229920003145 methacrylic acid copolymer Polymers 0.000 description 1
125000005397 methacrylic acid ester group Chemical group 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000010705 motor oil Substances 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
125000001400 nonyl 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])[H] 0.000 description 1
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-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
150000002894 organic compounds Chemical class 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
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 1
125000002460 pentacosyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000005060 rubber Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229920005573 silicon-containing polymer Polymers 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical group 0.000 description 1
125000002948 undecyl 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])[H] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
229910001868 water Inorganic materials 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
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- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- 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
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- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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- C10M2207/027—Neutral salts thereof
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- C10M2209/084—Acrylate; Methacrylate
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- C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
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- C10M2215/28—Amides; Imides
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- C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
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- C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
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- C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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- 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
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- 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—Overbased sulfonic acid salts
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- 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
- C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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- 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
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- 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
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- 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
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- 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
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- C10M2223/04—Phosphate esters
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- C10M2229/04—Siloxanes with specific structure
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- C10N2010/00—Metal present as such or in compounds
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Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Lubricants (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA304,268A 1977-07-28 1978-05-29 Non-cross linked products of hydrocarbon polymers with olefinic polar compounds and processes for making same Expired CA1134090A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81990877A	1977-07-28	1977-07-28
US819,908		1977-07-28

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CA1134090A true CA1134090A (en)	1982-10-19

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ID=25229408

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CA304,268A Expired CA1134090A (en)	1977-07-28	1978-05-29	Non-cross linked products of hydrocarbon polymers with olefinic polar compounds and processes for making same

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JP (1)	JPS5425902A (ja)
AU (1)	AU521904B2 (ja)
BE (1)	BE869377A (ja)
BR (1)	BR7804866A (ja)
CA (1)	CA1134090A (ja)
DE (1)	DE2832406A1 (ja)
ES (1)	ES472119A1 (ja)
FR (1)	FR2398795A1 (ja)
GB (1)	GB1601079A (ja)
IT (1)	IT1109480B (ja)
MX (1)	MX4953E (ja)
NL (1)	NL7807830A (ja)
ZA (1)	ZA783399B (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5298565A (en) *	1989-04-05	1994-03-29	The Lubrizol Corporation	Graft copolymers and lubricants containing such as dispersant-viscosity improvers

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4340689A (en) *	1979-09-17	1982-07-20	Copolymer Rubber & Chemical Corporation	Method of grafting EPM and EPDM polymers
EP0029622B1 (en) *	1979-11-16	1984-07-25	Shell Internationale Researchmaatschappij B.V.	Modified hydrogenated star-shaped polymer, its preparation and a lubricating oil composition containing the polymer
US4715975A (en) *	1984-08-20	1987-12-29	Texaco Inc.	Oil containing dispersant VII olefin copolymer
EP0199453A3 (en) *	1985-04-24	1988-04-13	Texaco Development Corporation	Hydrocarbon compositions containing polyolefin graft polymers
DE69028074T2 (de) *	1989-04-05	1997-03-06	The Lubrizol Corp., Wickliffe, Ohio	Pfropfmischpolymerisate und schmiermittel, die diese enthalten als dispergier- und viskositätsverbesserer
US5035820A (en) *	1990-05-15	1991-07-30	Shell Oil Company	Oil compositions containing modified star polymers
DE4427473A1 (de)	1994-08-03	1996-02-08	Roehm Gmbh	Motorenöle mit hohem Dispergiervermögen und gutem Verschleißschutz
US5663126A (en) *	1994-10-21	1997-09-02	Castrol Limited	Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them
US5523008A (en) *	1994-10-21	1996-06-04	Castrol Limited	Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them
CN110498889A (zh) *	2019-08-14	2019-11-26	深圳昆油石化技术有限公司	含有星型二元乙丙共聚物润滑油粘度指数改进剂组合物及其制备方法

1978
- 1978-05-17 GB GB20037/78A patent/GB1601079A/en not_active Expired
- 1978-05-29 CA CA304,268A patent/CA1134090A/en not_active Expired
- 1978-06-13 ZA ZA00783399A patent/ZA783399B/xx unknown
- 1978-06-21 AU AU37335/78A patent/AU521904B2/en not_active Expired
- 1978-07-03 JP JP7985078A patent/JPS5425902A/ja active Pending
- 1978-07-10 MX MX787214U patent/MX4953E/es unknown
- 1978-07-13 FR FR7820943A patent/FR2398795A1/fr not_active Withdrawn
- 1978-07-24 DE DE19782832406 patent/DE2832406A1/de not_active Ceased
- 1978-07-24 NL NL7807830A patent/NL7807830A/xx not_active Application Discontinuation
- 1978-07-27 IT IT26199/78A patent/IT1109480B/it active
- 1978-07-27 ES ES472119A patent/ES472119A1/es not_active Expired
- 1978-07-27 BR BR7804866A patent/BR7804866A/pt unknown
- 1978-07-28 BE BE189592A patent/BE869377A/xx unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5298565A (en) *	1989-04-05	1994-03-29	The Lubrizol Corporation	Graft copolymers and lubricants containing such as dispersant-viscosity improvers

Also Published As

Publication number	Publication date
NL7807830A (nl)	1979-01-30
BE869377A (fr)	1979-01-29
AU521904B2 (en)	1982-05-06
MX4953E (es)	1983-01-12
BR7804866A (pt)	1979-05-08
IT7826199A0 (it)	1978-07-27
FR2398795A1 (fr)	1979-02-23
ZA783399B (en)	1979-10-31
JPS5425902A (en)	1979-02-27
GB1601079A (en)	1981-10-21
ES472119A1 (es)	1979-03-16
IT1109480B (it)	1985-12-16
AU3733578A (en)	1980-01-03
DE2832406A1 (de)	1979-02-08

Legal Events

Date	Code	Title	Description
1999-10-19	MKEX	Expiry

Publication	Publication Date	Title
US3785980A (en)	1974-01-15	Reaction product of an amine and a hydroperoxidized ethylene/propylene copolymer
US5188745A (en)	1993-02-23	Viton seal compatible dispersant and lubricating oil composition containing same
US4743391A (en)	1988-05-10	Method for oxidatively degrading an olefinic polymer
CA1279318C (en)	1991-01-22	Hydrocarbon compositions containing polyolefin graft polymers
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US5409623A (en)	1995-04-25	Functionalized graft co-polymer as a viscosity and index improver, dispersant, and anti-oxidant additive and lubricating oil composition containing same
US5112508A (en)	1992-05-12	VI improver, dispersant, and antioxidant additive and lubricating oil composition
US5429757A (en)	1995-07-04	Multifunctional copolymer and lubricating oil composition
CA1271577A (en)	1990-07-10	Hydrocarbon compositions containing polyolefin graft polymers
EP0417904B1 (en)	1993-09-01	Method for producing dispersant, vi improver, additive for lubricating oil
EP0515152B1 (en)	1997-04-02	Dispersant additive and lubricating oil composition containing same
US5466387A (en)	1995-11-14	Oil-soluble adducts of disuccinimides and anhydrides of unsaturated bicarboxylic aliphatic acids
CA1184554A (en)	1985-03-26	Lubricating oil compositions
JP2930627B2 (ja)	1999-08-03	ビシナルなカルボキシル基を含有するコポリマーとプロピレンポリアミンとの縮合によって得られる潤滑剤添加剤
US4808325A (en)	1989-02-28	Mannich dispersant VI-improver blended with phenolic compound for improved storage stability
GB1601079A (en)	1981-10-21	Reaction products of hydrocarbon polymers with olefinic polyar compounds and processes for making same
US4866135A (en)	1989-09-12	Heterocyclic amine terminated, lactone modified, aminated viscosity modifiers of improved dispersancy
US3923930A (en)	1975-12-02	Graft polymers and lubricant compositions thereof
US5425888A (en)	1995-06-20	Polymeric additive for lubricating oils
SK281687B6 (sk)	2001-06-11	Aditívum a spôsob jeho prípravy
US5976202A (en)	1999-11-02	Reaction products of polyolefins with vinyl esters and their use as fuel and lubricant additives
US5147569A (en)	1992-09-15	Lubricant additive to enhance anti-wear, anti-oxidancy, and dispersancy thereof
CA1303016C (en)	1992-06-09	Olefinic hydrocarbon modification with sulfur imides
US5200102A (en)	1993-04-06	Multifunctional olefin copolymer and lubricating oil composition
US5514291A (en)	1996-05-07	Hydroxy aromatic compound Mannich base derivatives of amino-substituted polymers for oleaginous compositions

CA1134090A - Non-cross linked products of hydrocarbon polymers with olefinic polar compounds and processes for making same - Google Patents

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