JP5479101B2 - 架橋ポリマー - Google Patents
架橋ポリマー Download PDFInfo
- Publication number
- JP5479101B2 JP5479101B2 JP2009536431A JP2009536431A JP5479101B2 JP 5479101 B2 JP5479101 B2 JP 5479101B2 JP 2009536431 A JP2009536431 A JP 2009536431A JP 2009536431 A JP2009536431 A JP 2009536431A JP 5479101 B2 JP5479101 B2 JP 5479101B2
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- JP
- Japan
- Prior art keywords
- meth
- hydrocarbyl
- lubricating composition
- monomer
- polymer
- 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 - Fee Related
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- 229920006037 cross link polymer Polymers 0.000 title claims description 88
- 239000000178 monomer Substances 0.000 claims description 178
- 239000000203 mixture Substances 0.000 claims description 126
- 229920000642 polymer Polymers 0.000 claims description 91
- 230000001050 lubricating effect Effects 0.000 claims description 87
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 82
- 238000000034 method Methods 0.000 claims description 78
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 230000008569 process Effects 0.000 claims description 50
- -1 polyalkylstyrene Chemical class 0.000 claims description 49
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 47
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 32
- 230000001588 bifunctional effect Effects 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 238000010526 radical polymerization reaction Methods 0.000 claims description 18
- 229920001577 copolymer Polymers 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 230000005540 biological transmission Effects 0.000 claims description 9
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 9
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 8
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 8
- 238000002485 combustion reaction Methods 0.000 claims description 8
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
- 229920002125 Sokalan® Polymers 0.000 claims description 7
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 7
- 239000000314 lubricant Substances 0.000 claims description 7
- 239000004584 polyacrylic acid Substances 0.000 claims description 7
- 238000012546 transfer Methods 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 229920000098 polyolefin Polymers 0.000 claims description 5
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical class CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical class CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 229920002367 Polyisobutene Polymers 0.000 claims description 4
- 239000002174 Styrene-butadiene Substances 0.000 claims description 4
- 229920001400 block copolymer Polymers 0.000 claims description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- 229920005604 random copolymer Polymers 0.000 claims description 4
- 239000011115 styrene butadiene Substances 0.000 claims description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 239000003921 oil Substances 0.000 description 41
- 235000019198 oils Nutrition 0.000 description 41
- 239000003999 initiator Substances 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 19
- 239000000654 additive Substances 0.000 description 17
- 239000012986 chain transfer agent Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 230000009257 reactivity Effects 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 9
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 9
- 229920000193 polymethacrylate Polymers 0.000 description 9
- 239000002199 base oil Substances 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 239000012467 final product Substances 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000000446 fuel Substances 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- KOBJYYDWSKDEGY-UHFFFAOYSA-N 2-phenylpropan-2-yl benzenecarbodithioate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=S)C1=CC=CC=C1 KOBJYYDWSKDEGY-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000994 depressogenic effect Effects 0.000 description 4
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 3
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 3
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000004435 Oxo alcohol Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000012208 gear oil Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
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- 150000002924 oxiranes Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
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- 229920000058 polyacrylate Polymers 0.000 description 3
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- 150000008117 polysulfides Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 3
- 239000012989 trithiocarbonate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- PTYXPKUPXPWHSH-UHFFFAOYSA-N 1-(butyltetrasulfanyl)butane Chemical compound CCCCSSSSCCCC PTYXPKUPXPWHSH-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 2
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- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 2
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- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
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- 150000003568 thioethers Chemical class 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 239000012991 xanthate Substances 0.000 description 2
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- 239000011701 zinc Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- FNBPLKKPMRILKY-UHFFFAOYSA-N (4-ethenylphenyl)methyl benzenecarbodithioate Chemical compound C1=CC(C=C)=CC=C1CSC(=S)C1=CC=CC=C1 FNBPLKKPMRILKY-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
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- MGJYZNJAQSLHOL-UHFFFAOYSA-M n,n-dioctylcarbamodithioate Chemical compound CCCCCCCCN(C([S-])=S)CCCCCCCC MGJYZNJAQSLHOL-UHFFFAOYSA-M 0.000 description 1
- YQZKGAILXKHVKY-UHFFFAOYSA-N n-ethenyl-2-hydroxyacetamide Chemical compound OCC(=O)NC=C YQZKGAILXKHVKY-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- RCLLINSDAJVOHP-UHFFFAOYSA-N n-ethyl-n',n'-dimethylprop-2-enehydrazide Chemical compound CCN(N(C)C)C(=O)C=C RCLLINSDAJVOHP-UHFFFAOYSA-N 0.000 description 1
- JLSGYVNIIASPIZ-UHFFFAOYSA-N n-methylmethanamine;propyl 2-methylprop-2-enoate Chemical compound CNC.CCCOC(=O)C(C)=C JLSGYVNIIASPIZ-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 125000001196 nonadecyl 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])[H] 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
- AOAFIKNGZOOCRX-UHFFFAOYSA-N o-ethyl 1-phenylethylsulfanylmethanethioate Chemical compound CCOC(=S)SC(C)C1=CC=CC=C1 AOAFIKNGZOOCRX-UHFFFAOYSA-N 0.000 description 1
- HYURBBIIHCNUSC-UHFFFAOYSA-N o-ethyl cyanomethylsulfanylmethanethioate Chemical compound CCOC(=S)SCC#N HYURBBIIHCNUSC-UHFFFAOYSA-N 0.000 description 1
- DKKUKDFFFUHZPG-UHFFFAOYSA-N o-phenyl benzylsulfanylmethanethioate Chemical compound C=1C=CC=CC=1CSC(=S)OC1=CC=CC=C1 DKKUKDFFFUHZPG-UHFFFAOYSA-N 0.000 description 1
- LQNPIBHEOATAEO-UHFFFAOYSA-N octanoate;octylazanium Chemical compound CCCCCCCCN.CCCCCCCC(O)=O LQNPIBHEOATAEO-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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
- 238000005580 one pot reaction Methods 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
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 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 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- FIUNVVREDGDHKO-UHFFFAOYSA-N tert-butylsulfanyl benzenecarbodithioate Chemical compound CC(C)(C)SSC(=S)C1=CC=CC=C1 FIUNVVREDGDHKO-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals 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
- 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—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
- C10M145/12—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 monocarboxylic
- C10M145/14—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
- 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
- C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
-
- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/019—Shear stability
-
- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/68—Shear stability
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86486506P | 2006-11-08 | 2006-11-08 | |
| US60/864,865 | 2006-11-08 | ||
| PCT/US2007/083728 WO2008058108A2 (en) | 2006-11-08 | 2007-11-06 | Crosslinked polymer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010509465A JP2010509465A (ja) | 2010-03-25 |
| JP2010509465A5 JP2010509465A5 (enExample) | 2010-12-02 |
| JP5479101B2 true JP5479101B2 (ja) | 2014-04-23 |
Family
ID=39315126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009536431A Expired - Fee Related JP5479101B2 (ja) | 2006-11-08 | 2007-11-06 | 架橋ポリマー |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8012917B2 (enExample) |
| EP (1) | EP2087083A2 (enExample) |
| JP (1) | JP5479101B2 (enExample) |
| CN (1) | CN101548002B (enExample) |
| CA (1) | CA2667591A1 (enExample) |
| SG (1) | SG165412A1 (enExample) |
| WO (1) | WO2008058108A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101001246B1 (ko) * | 2007-01-31 | 2010-12-17 | 주식회사 엘지화학 | 토너 제조 방법 |
| JP5178220B2 (ja) * | 2008-01-31 | 2013-04-10 | 東京応化工業株式会社 | レジスト組成物およびレジストパターン形成方法 |
| KR101775172B1 (ko) | 2009-06-04 | 2017-09-05 | 더루우브리졸코오포레이션 | 고 ｖｉ 점도 조정제로서의 폴리메타크릴레이트 |
| WO2012076676A1 (en) | 2010-12-10 | 2012-06-14 | Evonik Rohmax Additives Gmbh | A viscosity index improver comprising a polyalkyl(meth)acrylate polymer |
| JP5525478B2 (ja) * | 2011-03-31 | 2014-06-18 | Ｊｘ日鉱日石エネルギー株式会社 | 粘度指数向上剤及び潤滑油組成物 |
| US20130130958A1 (en) * | 2011-11-22 | 2013-05-23 | Shell Oil Company | High molecular weight polymers as viscosity modifiers |
| EP2878659A4 (en) * | 2012-07-24 | 2016-03-09 | Jx Nippon Oil & Energy Corp | OIL COMPOSITION |
| EP2878658B1 (en) * | 2012-07-24 | 2018-09-05 | JX Nippon Oil & Energy Corporation | Lubricating oil composition |
| CN104395444B (zh) | 2012-07-24 | 2018-10-16 | 吉坤日矿日石能源株式会社 | 聚(甲基)丙烯酸酯系粘度指数改进剂、以及含有该粘度指数改进剂的润滑油添加剂及润滑油组合物 |
| WO2015164682A1 (en) * | 2014-04-25 | 2015-10-29 | The Lubrizol Corporation | Multigrade lubricating compositions |
| EP3472276A1 (en) * | 2016-06-17 | 2019-04-24 | Akzo Nobel Chemicals International B.V. | Lubricant spray polymers |
| EP3680313B1 (en) | 2016-06-17 | 2022-03-23 | Total Marketing Services | Lubricant polymers |
| WO2017216332A1 (en) * | 2016-06-17 | 2017-12-21 | Akzo Nobel Chemicals International B.V. | Lubricant spray polymers |
| US10369445B2 (en) * | 2016-08-10 | 2019-08-06 | Stephen Joseph Stemle | Video analytics for human performance |
| WO2025036294A1 (zh) * | 2023-08-11 | 2025-02-20 | 科凝生物制药(深圳)有限公司 | 嵌段式共聚物的润滑组合物及其用途 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB759918A (en) | 1952-10-22 | 1956-10-24 | California Research Corp | Lubricant composition |
| FR1361857A (fr) * | 1961-11-30 | 1964-05-29 | Exxon Research Engineering Co | Améliorations apportées à la fabrication de produits d'addition aux compositions lubrifiantes |
| NL109759C (enExample) * | 1961-12-29 | |||
| US4086296A (en) * | 1970-07-17 | 1978-04-25 | Rohm And Haas Company | Blends of thermoplastic polymer with a multi-phase acrylic composite polymers |
| US5274063A (en) * | 1990-12-26 | 1993-12-28 | Kyoeisha Chemical Co., Ltd. | Vinyl polymer having (meth)acryloyl groups on the side chains and method for preparing same |
| FR2680791B1 (fr) * | 1991-08-30 | 1994-09-09 | Bp Chemicals Snc | Procede de fabrication d'un polymere reticule et utilisation du polymere. |
| US5552491A (en) * | 1995-01-27 | 1996-09-03 | Ethyl Additives Corporation | Star-branched acrylate and methacrylate polymers |
| EP1015532B1 (en) * | 1997-08-22 | 2004-11-17 | Rohmax Additives GmbH | Method for improving low-temperature fluidity of lubricating oils using high- and low-molecular weight polymer additive mixtures |
| US6013735A (en) * | 1998-02-13 | 2000-01-11 | Ethyl Corporation | Process for the preparation of acrylate and methacrylate polymers |
| US5955405A (en) * | 1998-08-10 | 1999-09-21 | Ethyl Corporation | (Meth) acrylate copolymers having excellent low temperature properties |
| US6391996B1 (en) | 1999-11-30 | 2002-05-21 | Rohmax Additives Gmbh | Copolymers obtainable by the ATRP method and a method for their preparation and their use |
| JP4691315B2 (ja) * | 2003-05-30 | 2011-06-01 | 三洋化成工業株式会社 | 流動点降下剤および炭化水素油組成物 |
| JP5078087B2 (ja) | 2004-10-25 | 2012-11-21 | ザ ルブリゾル コーポレイション | 星形重合体およびそれらの組成物 |
| CA2584907C (en) * | 2004-10-25 | 2013-09-24 | The Lubrizol Corporation | Process for preparing polymers and compositions thereof |
| US7906468B2 (en) * | 2005-02-23 | 2011-03-15 | Arkema Inc. | Acrylic block copolymer low temperature flow modifiers in lubricating oils |
| AU2007243015B2 (en) * | 2006-04-24 | 2011-07-21 | The Lubrizol Corporation | Star polymer lubricating composition |
| US7696138B2 (en) * | 2006-07-28 | 2010-04-13 | Afton Chemical Corporation | Alkyl acrylate copolymer dispersants and uses thereof |
-
2007
- 2007-11-06 EP EP07863954A patent/EP2087083A2/en not_active Withdrawn
- 2007-11-06 WO PCT/US2007/083728 patent/WO2008058108A2/en not_active Ceased
- 2007-11-06 CN CN2007800416528A patent/CN101548002B/zh not_active Expired - Fee Related
- 2007-11-06 US US12/447,999 patent/US8012917B2/en active Active
- 2007-11-06 SG SG201006914-4A patent/SG165412A1/en unknown
- 2007-11-06 CA CA002667591A patent/CA2667591A1/en not_active Abandoned
- 2007-11-06 JP JP2009536431A patent/JP5479101B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101548002B (zh) | 2013-04-24 |
| JP2010509465A (ja) | 2010-03-25 |
| CA2667591A1 (en) | 2008-05-15 |
| CN101548002A (zh) | 2009-09-30 |
| WO2008058108A3 (en) | 2008-10-02 |
| WO2008058108A2 (en) | 2008-05-15 |
| US8012917B2 (en) | 2011-09-06 |
| US20100004149A1 (en) | 2010-01-07 |
| SG165412A1 (en) | 2010-10-28 |
| EP2087083A2 (en) | 2009-08-12 |
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