JP2019516828A - ポリオレフィン骨格およびメタクリレート側鎖をベースとするグラフトコポリマー - Google Patents
ポリオレフィン骨格およびメタクリレート側鎖をベースとするグラフトコポリマー Download PDFInfo
- Publication number
- JP2019516828A JP2019516828A JP2018559793A JP2018559793A JP2019516828A JP 2019516828 A JP2019516828 A JP 2019516828A JP 2018559793 A JP2018559793 A JP 2018559793A JP 2018559793 A JP2018559793 A JP 2018559793A JP 2019516828 A JP2019516828 A JP 2019516828A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- graft copolymer
- compound
- segment
- carbon atoms
- 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.)
- Granted
Links
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 131
- 229920000098 polyolefin Polymers 0.000 title description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title description 10
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims abstract description 55
- 239000000654 additive Substances 0.000 claims abstract description 30
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims abstract description 29
- 238000002485 combustion reaction Methods 0.000 claims abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 131
- 229920000642 polymer Polymers 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 77
- 239000002199 base oil Substances 0.000 claims description 75
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 60
- 239000000314 lubricant Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 31
- 239000003921 oil Substances 0.000 claims description 24
- 239000004913 cyclooctene Substances 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 229920001577 copolymer Polymers 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 14
- 230000000996 additive effect Effects 0.000 claims description 12
- 150000002430 hydrocarbons Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000006185 dispersion Substances 0.000 claims description 8
- JUGDCQPILIWQIG-UHFFFAOYSA-N 3-ethylcyclooctene Chemical compound CCC1CCCCCC=C1 JUGDCQPILIWQIG-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 3
- 239000007870 radical polymerization initiator Substances 0.000 claims description 3
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 77
- 238000012546 transfer Methods 0.000 abstract description 5
- 150000001925 cycloalkenes Chemical class 0.000 abstract description 4
- 101710141544 Allatotropin-related peptide Proteins 0.000 abstract 1
- -1 alkyl methacrylates Chemical class 0.000 description 103
- 239000000178 monomer Substances 0.000 description 45
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 30
- 239000002480 mineral oil Substances 0.000 description 27
- 230000008719 thickening Effects 0.000 description 23
- 239000003999 initiator Substances 0.000 description 19
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 18
- 235000010446 mineral oil Nutrition 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 150000001298 alcohols Chemical class 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000010687 lubricating oil Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 229920013639 polyalphaolefin Polymers 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 238000005984 hydrogenation reaction Methods 0.000 description 11
- 235000001508 sulfur Nutrition 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000000446 fuel Substances 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000003158 alcohol group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012986 chain transfer agent Substances 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
- 239000010705 motor oil Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 238000001542 size-exclusion chromatography Methods 0.000 description 6
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000004103 aminoalkyl group Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- 235000014786 phosphorus Nutrition 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- XXSPGBOGLXKMDU-UHFFFAOYSA-N 2-bromo-2-methylpropanoic acid Chemical group CC(C)(Br)C(O)=O XXSPGBOGLXKMDU-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 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 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 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 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003440 styrenes Chemical class 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000004435 Oxo alcohol Substances 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007866 anti-wear additive Substances 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 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 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000009878 intermolecular interaction Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005649 metathesis reaction Methods 0.000 description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 229920000196 poly(lauryl methacrylate) Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003871 sulfonates Chemical class 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
- 150000003623 transition metal compounds Chemical class 0.000 description 3
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 3
- 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 2
- IRUCBBFNLDIMIK-FPLPWBNLSA-N (z)-oct-4-ene Chemical compound CCC\C=C/CCC IRUCBBFNLDIMIK-FPLPWBNLSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- XVTPGZQPUZSUKS-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN1CCCC1=O XVTPGZQPUZSUKS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DJKKWVGWYCKUFC-UHFFFAOYSA-N 2-butoxyethyl 2-methylprop-2-enoate Chemical compound CCCCOCCOC(=O)C(C)=C DJKKWVGWYCKUFC-UHFFFAOYSA-N 0.000 description 2
- KQWDURCUENVKII-UHFFFAOYSA-N 2-ethoxyethoxymethyl 2-methylprop-2-enoate Chemical compound CCOCCOCOC(=O)C(C)=C KQWDURCUENVKII-UHFFFAOYSA-N 0.000 description 2
- BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 description 2
- JNDVNJWCRZQGFQ-UHFFFAOYSA-N 2-methyl-N,N-bis(methylamino)hex-2-enamide Chemical compound CCCC=C(C)C(=O)N(NC)NC JNDVNJWCRZQGFQ-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 2
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000005069 Extreme pressure additive Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical class [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000005865 alkene metathesis reaction Methods 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 2
- 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 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000006392 deoxygenation reaction Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002272 engine oil additive Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000010720 hydraulic oil Substances 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000003077 lignite Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 2
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 2
- 238000012705 nitroxide-mediated radical polymerization Methods 0.000 description 2
- 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 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 2
- 150000002895 organic esters Chemical class 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 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 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001083 polybutene Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000007858 starting material 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
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 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
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- RUKVGXGTVPPWDD-UHFFFAOYSA-N 1,3-bis(2,4,6-trimethylphenyl)imidazolidine Chemical group CC1=CC(C)=CC(C)=C1N1CN(C=2C(=CC(C)=CC=2C)C)CC1 RUKVGXGTVPPWDD-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical class C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- JQACBLYOTAYMHP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyl)pyrrolidin-2-one Chemical compound CC(=C)C(=O)N1CCCC1=O JQACBLYOTAYMHP-UHFFFAOYSA-N 0.000 description 1
- INMCBHAUNITFAQ-UHFFFAOYSA-N 1-(2-oxopyrrolidin-1-yl)heptadecan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCC(OC(=O)C(C)=C)CCN1CCCC1=O INMCBHAUNITFAQ-UHFFFAOYSA-N 0.000 description 1
- PYGSHOKARRMFTD-UHFFFAOYSA-N 1-(2-oxopyrrolidin-1-yl)pentadecan-2-yl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCC(OC(=O)C(C)=C)CN1CCCC1=O PYGSHOKARRMFTD-UHFFFAOYSA-N 0.000 description 1
- HMLSBRLVTDLLOI-UHFFFAOYSA-N 1-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)C(C)OC(=O)C(C)=C HMLSBRLVTDLLOI-UHFFFAOYSA-N 0.000 description 1
- VFUAIQLFDVVAPZ-UHFFFAOYSA-N 1-[diethoxy(propoxy)silyl]-2-methylprop-2-en-1-one Chemical compound CCCO[Si](C(C(=C)C)=O)(OCC)OCC VFUAIQLFDVVAPZ-UHFFFAOYSA-N 0.000 description 1
- DDPGLQRMAQYQEQ-UHFFFAOYSA-N 1-butoxypropyl 2-methylprop-2-enoate Chemical compound CCCCOC(CC)OC(=O)C(C)=C DDPGLQRMAQYQEQ-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- WIWZLDGSODDMHJ-UHFFFAOYSA-N 1-ethoxybutyl 2-methylprop-2-enoate Chemical compound CCCC(OCC)OC(=O)C(C)=C WIWZLDGSODDMHJ-UHFFFAOYSA-N 0.000 description 1
- HVBADOTWUFBZMF-UHFFFAOYSA-N 1-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOC(C)OC(=O)C(C)=C HVBADOTWUFBZMF-UHFFFAOYSA-N 0.000 description 1
- CYLREEOZWJVJSE-UHFFFAOYSA-N 1-ethylcyclooctene Chemical compound CCC1=CCCCCCC1 CYLREEOZWJVJSE-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- OQYKKQQLTKPGSG-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diol Chemical compound OCC(C)CCC(C)CO OQYKKQQLTKPGSG-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- PHWTWSHIYPDGEL-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]phenol;2,6-ditert-butyl-4-methylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 PHWTWSHIYPDGEL-UHFFFAOYSA-N 0.000 description 1
- PQDKOKTULASSPO-UHFFFAOYSA-N 2-(1,3-oxazolidin-2-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1NCCO1 PQDKOKTULASSPO-UHFFFAOYSA-N 0.000 description 1
- MGMSZKIPUNOMCS-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC=C MGMSZKIPUNOMCS-UHFFFAOYSA-N 0.000 description 1
- DAVVKEZTUOGEAK-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound COCCOCCOC(=O)C(C)=C DAVVKEZTUOGEAK-UHFFFAOYSA-N 0.000 description 1
- FPCPOLLWTJARLO-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)acetic acid Chemical compound CC(=C)C(=O)OCC(O)=O FPCPOLLWTJARLO-UHFFFAOYSA-N 0.000 description 1
- NISAHDHKGPWBEM-UHFFFAOYSA-N 2-(4-nonylphenoxy)acetic acid Chemical compound CCCCCCCCCC1=CC=C(OCC(O)=O)C=C1 NISAHDHKGPWBEM-UHFFFAOYSA-N 0.000 description 1
- KZUIKPMQAIEBOE-UHFFFAOYSA-N 2-(ethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCNCCOC(=O)C(C)=C KZUIKPMQAIEBOE-UHFFFAOYSA-N 0.000 description 1
- PDTDJRYFNGKLHD-UHFFFAOYSA-N 2-(methoxymethoxy)ethyl 2-methylprop-2-enoate Chemical compound COCOCCOC(=O)C(C)=C PDTDJRYFNGKLHD-UHFFFAOYSA-N 0.000 description 1
- PTBAHIRKWPUZAM-UHFFFAOYSA-N 2-(oxiran-2-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1CO1 PTBAHIRKWPUZAM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- AXXUFOMEPPBIHV-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethylsulfanyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCSCCOC(=O)C(C)=C AXXUFOMEPPBIHV-UHFFFAOYSA-N 0.000 description 1
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 1
- RURPJGZXBHYNEM-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]propyliminomethyl]phenol Chemical compound C=1C=CC=C(O)C=1C=NC(C)CN=CC1=CC=CC=C1O RURPJGZXBHYNEM-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- FHPGUDZEMVTLRC-UHFFFAOYSA-N 2-ethylsulfonylethyl 2-methylprop-2-enoate Chemical compound CCS(=O)(=O)CCOC(=O)C(C)=C FHPGUDZEMVTLRC-UHFFFAOYSA-N 0.000 description 1
- SFXIMNQKTHLNEN-UHFFFAOYSA-N 2-hexadecylicosyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCC(COC(=O)C(C)=C)CCCCCCCCCCCCCCCC SFXIMNQKTHLNEN-UHFFFAOYSA-N 0.000 description 1
- UYXQLQUXXCIFQM-UHFFFAOYSA-N 2-hydroxy-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound OP1(=O)OCCO1 UYXQLQUXXCIFQM-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- KXVAYZZWCKNUMN-UHFFFAOYSA-N 2-imidazol-1-ylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN1C=CN=C1 KXVAYZZWCKNUMN-UHFFFAOYSA-N 0.000 description 1
- AKVUWTYSNLGBJY-UHFFFAOYSA-N 2-methyl-1-morpholin-4-ylprop-2-en-1-one Chemical compound CC(=C)C(=O)N1CCOCC1 AKVUWTYSNLGBJY-UHFFFAOYSA-N 0.000 description 1
- GASMGDMKGYYAHY-UHFFFAOYSA-N 2-methylidenehexanamide Chemical group CCCCC(=C)C(N)=O GASMGDMKGYYAHY-UHFFFAOYSA-N 0.000 description 1
- GNLLVGLBEKGLTI-UHFFFAOYSA-N 2-methylprop-1-ene;pyrrolidine-2,5-dione Chemical compound CC(C)=C.O=C1CCC(=O)N1 GNLLVGLBEKGLTI-UHFFFAOYSA-N 0.000 description 1
- MNZNJOQNLFEAKG-UHFFFAOYSA-N 2-morpholin-4-ylethyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCCN1CCOCC1 MNZNJOQNLFEAKG-UHFFFAOYSA-N 0.000 description 1
- UMNGRRUQHFCWGR-UHFFFAOYSA-N 2-oxopropyl 2-methylprop-2-enoate Chemical compound CC(=O)COC(=O)C(C)=C UMNGRRUQHFCWGR-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- JTFIUWWKGBGREU-UHFFFAOYSA-N 3,4-dihydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(O)CO JTFIUWWKGBGREU-UHFFFAOYSA-N 0.000 description 1
- SBWOBTUYQXLKSS-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propanoic acid Chemical compound CC(=C)C(=O)OCCC(O)=O SBWOBTUYQXLKSS-UHFFFAOYSA-N 0.000 description 1
- LOKFVYOYLXCQMI-UHFFFAOYSA-N 3-(2-oxopyrrolidin-1-yl)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCN1CCCC1=O LOKFVYOYLXCQMI-UHFFFAOYSA-N 0.000 description 1
- MXDJEURPLCKZKK-UHFFFAOYSA-N 3-(cyanoamino)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCNC#N MXDJEURPLCKZKK-UHFFFAOYSA-N 0.000 description 1
- AULRQPKOXIXXFI-UHFFFAOYSA-N 3-(diethylamino)pentyl 2-methylprop-2-enoate Chemical compound CCN(CC)C(CC)CCOC(=O)C(C)=C AULRQPKOXIXXFI-UHFFFAOYSA-N 0.000 description 1
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 1
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-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
- BDJJXYDGLDDYDU-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-5-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCC2OC12 BDJJXYDGLDDYDU-UHFFFAOYSA-N 0.000 description 1
- FAWVUVUSQZTKCT-UHFFFAOYSA-N 9-(3-pentyloxiran-2-yl)nonyl 2-methylprop-2-enoate Chemical compound CCCCCC1OC1CCCCCCCCCOC(=O)C(C)=C FAWVUVUSQZTKCT-UHFFFAOYSA-N 0.000 description 1
- DGZNXJPBIXMBJR-UHFFFAOYSA-N 9-(oxiran-2-yl)nonyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCC1CO1 DGZNXJPBIXMBJR-UHFFFAOYSA-N 0.000 description 1
- 108700015862 A-B-A triblock copolymer Proteins 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 101000734336 Arabidopsis thaliana Protein disulfide isomerase-like 1-2 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- MJXQPJARQNKSRO-UHFFFAOYSA-N C(CCCCCCCCCCC)C=C(C(=O)O)C.C(C(=C)C)(=O)OCCCCCCCCCCCC Chemical compound C(CCCCCCCCCCC)C=C(C(=O)O)C.C(C(=C)C)(=O)OCCCCCCCCCCCC MJXQPJARQNKSRO-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- CUDSBWGCGSUXDB-UHFFFAOYSA-N Dibutyl disulfide Chemical group CCCCSSCCCC CUDSBWGCGSUXDB-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N N-methylaminoacetic acid Natural products C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000947853 Vibrionales Species 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- XYRMLECORMNZEY-UHFFFAOYSA-B [Mo+4].[Mo+4].[Mo+4].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S Chemical compound [Mo+4].[Mo+4].[Mo+4].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S XYRMLECORMNZEY-UHFFFAOYSA-B 0.000 description 1
- YXJSJLIZOYQKEY-UHFFFAOYSA-N acetonitrile 2-methylprop-2-enamide Chemical compound CC#N.CC(=C)C(N)=O YXJSJLIZOYQKEY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003342 alkenyl 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000010718 automatic transmission oil Substances 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
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- FCDPQMAOJARMTG-UHFFFAOYSA-L benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichlororuthenium;tricyclohexylphosphane Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1.CC1=CC(C)=CC(C)=C1N(CCN1C=2C(=CC(C)=CC=2C)C)C1=[Ru](Cl)(Cl)=CC1=CC=CC=C1 FCDPQMAOJARMTG-UHFFFAOYSA-L 0.000 description 1
- FCDPQMAOJARMTG-UHFFFAOYSA-M benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichlororuthenium;tricyclohexylphosphanium Chemical compound C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.CC1=CC(C)=CC(C)=C1N(CCN1C=2C(=CC(C)=CC=2C)C)C1=[Ru](Cl)(Cl)=CC1=CC=CC=C1 FCDPQMAOJARMTG-UHFFFAOYSA-M 0.000 description 1
- UNOMOKBVBBHHMU-UHFFFAOYSA-N benzylidene-dicyclohexyl-(4,4-dichlorocyclohexyl)-lambda5-phosphane ruthenium Chemical compound [Ru].ClC1(Cl)CCC(CC1)P(=Cc1ccccc1)(C1CCCCC1)C1CCCCC1 UNOMOKBVBBHHMU-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000033558 biomineral tissue development Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- SQHOHKQMTHROSF-UHFFFAOYSA-N but-1-en-2-ylbenzene Chemical compound CCC(=C)C1=CC=CC=C1 SQHOHKQMTHROSF-UHFFFAOYSA-N 0.000 description 1
- RTACIUYXLGWTAE-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene;styrene Chemical compound C=CC=C.CC(=C)C=C.C=CC1=CC=CC=C1 RTACIUYXLGWTAE-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-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
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 238000012668 chain scission Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- KXTNMKREYTVOMX-UHFFFAOYSA-N cyanomethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC#N KXTNMKREYTVOMX-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- XRXPHPJRVWEWKQ-UHFFFAOYSA-N cyclohexyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC1CCCCC1 XRXPHPJRVWEWKQ-UHFFFAOYSA-N 0.000 description 1
- 125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 125000003074 decanoyl 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(*)=O 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
- OKIWPZFGXYWTNW-UHFFFAOYSA-N dipropoxyphosphoryl 2-methylprop-2-enoate Chemical compound CCCOP(=O)(OCCC)OC(=O)C(C)=C OKIWPZFGXYWTNW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- WMAFNLQQGPUKCM-UHFFFAOYSA-N ethoxymethyl 2-methylprop-2-enoate Chemical compound CCOCOC(=O)C(C)=C WMAFNLQQGPUKCM-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001595 flow curve Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- DWXAVNJYFLGAEF-UHFFFAOYSA-N furan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CO1 DWXAVNJYFLGAEF-UHFFFAOYSA-N 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000011984 grubbs catalyst Substances 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- CFBXDFZIDLWOSO-UHFFFAOYSA-N icosyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C(C)=C CFBXDFZIDLWOSO-UHFFFAOYSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 238000011545 laboratory measurement Methods 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- LVQPBIMCRZQQBC-UHFFFAOYSA-N methoxymethyl 2-methylprop-2-enoate Chemical compound COCOC(=O)C(C)=C LVQPBIMCRZQQBC-UHFFFAOYSA-N 0.000 description 1
- YVKIOPQNPJMZIJ-UHFFFAOYSA-N methylsulfinylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCS(C)=O YVKIOPQNPJMZIJ-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical compound C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 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
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-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
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- YGPZXPHFJSYIKP-UHFFFAOYSA-N nonadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCOC(=O)C(C)=C YGPZXPHFJSYIKP-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 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
- YOTGRUGZMVCBLS-UHFFFAOYSA-N pentadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C(C)=C YOTGRUGZMVCBLS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XGRBZUSXGVNWMI-UHFFFAOYSA-N phenylmethoxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOCC1=CC=CC=C1 XGRBZUSXGVNWMI-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000011986 second-generation catalyst Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- AKZDWOQGSQXGID-UHFFFAOYSA-N thiocyanatomethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCSC#N AKZDWOQGSQXGID-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- KXCGIVLTZXDSBO-UHFFFAOYSA-L zinc;n-pentylcarbamodithioate Chemical compound [Zn+2].CCCCCNC([S-])=S.CCCCCNC([S-])=S KXCGIVLTZXDSBO-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 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
- 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
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
- C08F220/68—Esters
-
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/08—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having four or more carbon atoms
-
- 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
- C08F277/00—Macromolecular compounds obtained by polymerising monomers on to polymers of carbocyclic or heterocyclic monomers as defined respectively in group C08F32/00 or in group C08F34/00
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/14—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers obtained by ring-opening polymerisation of carbocyclic compounds having one or more carbon-to-carbon double bonds in the carbocyclic ring, i.e. polyalkeneamers
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/005—Macromolecular compounds, e.g. macromolecular compounds composed of alternatively specified monomers not covered by the same main group
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
-
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/13—Morphological aspects
- C08G2261/136—Comb-like structures
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3322—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from cyclooctene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/418—Ring opening metathesis polymerisation [ROMP]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/74—Further polymerisation of the obtained polymers, e.g. living polymerisation to obtain block-copolymers
-
- 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
- C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions used as base material
-
- 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
- C10M2203/1025—Aliphatic fractions used as base material
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/022—Ethene
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/10—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing cycloaliphatic monomers
-
- 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
- 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
- C10N2020/02—Viscosity; 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
- 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
- C10N2030/68—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
- C10N2040/25—Internal-combustion engines
Landscapes
- 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)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
上記のポリマーは、広範囲の用途に商業的に使用されている。それにもかかわらず、マルチグレードエンジンオイルに使用するための増粘効率(TE)が向上した新規な粘度向上ポリマーを開発するための取組が進行中である。150℃での所定の高温高せん断(HTHS)(HTHS150)に従って配合されたとき、櫛形ポリマーを配合した潤滑剤の100℃での動粘度(KV)(KV100)は、エンジン部品を保護するのに十分高くなければならない。同時に、ポリマーの粘度指数(VI)は、低温での燃料経済性の目的で40℃での動粘度(KV40)を適度に低く維持するために、できる限り高くなければならない。増粘効率の向上は、より低い添加率および経済的利益をもたらすであろう。
本発明は、骨格に、置換されていてもよいシクロアルケンの開環メタセシス重合(ROMP)によって得られる繰り返し単位を有する少なくとも1つのセグメントと、側鎖に、(メタ)アクリレートの原子移動ラジカル重合(ATRP)によって得られる繰り返し単位を含む少なくとも1つのセグメントとを含むグラフトコポリマーが、優れた増粘効率、高い粘度指数および100℃での高い動粘度(KV100)を有するという驚くべき知見に基づく。したがって、対応するグラフトコポリマーは、内燃機関、特に実質的に一定の作動温度でより長期間運転される内燃機関でのオイル添加剤としての使用に非常に適している。
本発明の1つの態様は、グラフトコポリマーであって、骨格に少なくとも1つのセグメントAを含み、側鎖に少なくとも1つのセグメントBを含み、
セグメントAが、式(I):
R1は、水素原子であるか、または1〜40個の炭素原子を有し、置換されていてもよい炭化水素基である]で表される少なくとも1種の化合物と、
置換されていてもよいシクロアルケニル置換基を有する少なくとも1種のATRP開始剤と
のROMPによって得られる繰り返し単位を含み、
セグメントBが、式(II):
R2は、水素原子であるか、またはメチル基であり、
R3は、2〜40個の炭素原子を有し、置換されていてもよい炭化水素基である]で表される少なくとも1種の化合物のATRPによって得られる繰り返し単位を含む、グラフトコポリマーに関する。
R10、R11およびR12は、独立して、水素原子または1〜5個の炭素原子を有する線状もしくは分岐状のアルキル基であり、
R13は、C(Y)X−R14基であり、X=OもしくはX=NHであり、Yが(=O)または(=NR15)であり、
R15は、1〜8個の炭素原子を有するアルキル基またはアリール基であり、
R14は、−NR16R17基で置換された1〜20個の炭素原子を有する線状もしくは分岐状のアルキル基を表し、R16およびR17は、独立して、水素原子を表すか、または1〜8個の炭素原子を有する線状もしくは分岐状のアルキル基を表し、またはR16およびR17は、それらが結合している窒素と一緒になって、窒素、酸素もしくは硫黄からなる群から選択される1個以上のヘテロ原子を任意に含む4〜8員の飽和環もしくは不飽和環を形成し、前記環はさらにアルキル基またはアリール基で置換されていてよく、または
R13は、NR18R19基であり、R18およびR19は、それらが結合している窒素と一緒になって、窒素、酸素もしくは硫黄からなる群から選択されるヘテロ原子に対する二重結合を形成する環の一部として少なくとも1個の炭素原子を含む4〜8員の飽和環もしくは不飽和環を形成し、前記環はさらにアルキル基またはアリール基で置換されていてよい]のN−分散剤モノマーであってよい。
本発明の更なる態様は、上記のグラフトコポリマーを製造する方法に関する。この方法は、以下の工程:
(a)式(I)の少なくとも1種の化合物と、置換されていてもよいシクロアルケニル置換基を有するATRP開始剤とを含む混合物のROMPを行って、ポリマーAを得る工程;
(b)工程(a)で得られたポリマーAの存在下で式(II)の化合物のATRPを行って、ポリマーBを得る工程;
(c)工程(b)で得られたポリマーBの水素化を行って、本発明のグラフトコポリマーを得る工程
を含む。
本発明の更なる態様は、基油と上記の少なくとも1種のコポリマーとを含む潤滑剤組成物に関する。
約18〜31個の炭素原子を有するn−アルカン:
0.7〜1.0%、
18〜31個の炭素原子を有する僅かに分岐したアルカン:
1.0〜8.0%、
14〜32個の炭素原子を有する芳香族化合物:
0.4〜10.7%、
20〜32個の炭素原子を有するイソアルカンおよびシクロアルカン:
60.7〜82.4%、
極性化合物:
0.1〜0.8%、
損失分:
6.9〜19.4%。
材料:シクロオクテン(95%)、シス−4−オクテン(97%)、ブチル−およびラウリルメチルメタクリレートを商業的供給元から購入し、必要に応じて減圧蒸留により精製した。Neste Oil N.V.(ベルギー)製のグループIII基油NexBase(登録商標)3043を、潤滑剤組成物の調製に使用した。NexBase(登録商標)3043は、0.831g/mlの密度を有し、水素化された高度イソパラフィン性炭化水素を含む、接触水素化異性化および脱蝋された無色の基油である。
本発明のグラフトコポリマーP1〜P10を、スキーム2に示される手順に従って合成した:
ポリマーAの合成は、Y.Xuらの手順に従って行った(Macromolecules,2012,45,9604−9610)。
三つ口フラスコ中で、ポリオレフィン前駆体(PO−Br)、ブチルメタクリレート(BuMA)、ラウリルメタクリレート(LMA)、2−エチルヘキサン酸錫(II)(Sn(EH)2)およびN,N,N’,N’’,N’’−ペンタメチルジエチレン−トリアミン(PMDETA)の溶液を、CuBr2の添加前に30分間アルゴンバブリングすることによって完全に脱気した。反応物である[モノマー]:[PO−Br]:[CuBr2]:[Sn(EH)2]:[PMDETA]の最終モル比は、電子移動(ARGET)原子移動ラジカル重合(ATRP)により再生された活性化剤中で2000:1:0.1:0.5:0.1であった。反応混合物を70℃で16時間撹拌した後、氷浴で冷却し、空気中に開放した。ポリマーをメタノールから沈殿させ、乾燥させ、クロロホルムに溶解し、塩基性アルミナカラムに通して、色彩に富んだ残留銅触媒を除去した。最終ポリマーBを、大過剰のメタノールからの別の沈殿および真空中での一晩の乾燥によって得た。
工程(b)で得られたポリマーB、p−トシルヒドラジド、トリブチルアミンおよび微量のBHTの混合物を、トルエンと共に3時間還流し、室温まで冷却させた。大過剰のメタノールからの沈殿により水素化ポリマーを回収し、一晩真空乾燥させた。
b SECにより測定。
Mn bは、全グラフトコポリマーの分子量Mnを表す。
c 1H−NMRから計算。
Mn cは、メタクリレート繰り返し単位の数に基づき計算された側鎖の全体の分子量Mnを表す。
表2に列挙したグラフトコポリマーP1〜P3を、90℃で一晩撹拌することによりグループ(III)基油、Nexbase(登録商標)3043に溶解した。得られた潤滑剤組成物を、20℃の間隔で0℃〜140℃の間に加熱し、動粘度を測定した。
・粘度および基油とは無関係である、ポリマーのVI性能
・基油粘度とは無関係である、ある一定の基油の溶解力に対する増粘効率
の尺度である。
P5
水素化ポリ(LMA320BuMA490−g−COE250EtCOE700)
P9
水素化ポリ(LMA280BuMA440−g−COE340)
ポリオレフィン骨格およびPAMA側鎖を有するグラフトコポリマーをベースとする一連の潤滑添加剤を、逐次に環状モノマーのROMPならびにブチル−およびラウリルメタクリレートのARGET ATRPによって合成した。油溶性ポリマーは水素化によって得られ、0〜140℃の温度範囲にわたる粘度特性を試験した。[LMA]:[BuMA]のモル比を調整して、グラフトコポリマーの最適な溶解度性能を達成し、反応変換率を変えて、側鎖の所望のモル質量を達成した。側鎖極性が高いほど、ポリマーの溶解度の限界内で、BuMA60%のモル割合がより効果的であると結論付けることができる。それに、より高いVIが、側鎖により高いモル質量を有するグラフトコポリマーを配合した潤滑剤について観察された。さらに、骨格の結晶化度がグラフトコポリマーの粘度改質性能に直接影響を及ぼすことが示された。
グラフトコポリマーP3を、90℃で一晩撹拌することによりグループ(III)基油、Nexbase(登録商標)3043に溶解した。5重量%のP3を含む潤滑剤組成物のせん断速度による粘度の変化を、40℃および100℃で測定した。
本発明のグラフトコポリマーP5およびP9ならびに参考例、線状OCPおよびオレフィン星形コポリマーを、90℃で一晩撹拌することによりグループ(III)基油、Nexbase(登録商標)3043に溶解した。続けて、得られた潤滑剤組成物の動粘度、粘度指数(VI)およびHTHSを測定した。
本発明のグラフトコポリマーP5、P7、P8およびP9ならびに先行技術から公知の参考例、PAMA(Viscoplex(登録商標)3−500、Evonikから市販されている)および線状OCP(Lubrizol(登録商標)7077、約50/50重量%の比でエチレンとプロピレンとから製造されたオレフィンコポリマー、PMMA標準に基づいて約170,000g/molの重量平均分子量、PDI2,1)を、90℃で一晩撹拌することによりグループ(III)基油、Nexbase(登録商標)3043に溶解した。続けて、得られた潤滑剤組成物の動粘度および粘度指数(VI)を測定した。
Claims (15)
- グラフトコポリマーであって、骨格に少なくとも1つのセグメントAを含み、側鎖に少なくとも1つのセグメントBを含み、
前記セグメントAが、式(I):
R1は、水素原子であるか、または1〜40個の炭素原子を有し、置換されていてもよい炭化水素基である]で表される少なくとも1種の化合物と、
置換されていてもよいシクロアルケニル置換基を有する少なくとも1種の原子移動ラジカル重合開始剤と
の開環メタセシス重合によって得られる繰り返し単位を含み、
前記セグメントBが、式(II):
R2は、水素原子またはメチル基であり、
R3は、2〜40個の炭素原子を有し、置換されていてもよい炭化水素基である]で表される少なくとも1種の化合物の原子移動ラジカル重合によって得られる繰り返し単位を含む、グラフトコポリマー。 - 前記セグメントBが、少なくとも、
式(II)で表される第1の化合物であって、式中、R2は、メチル基であり、R3は、2〜5個の炭素原子、好ましくは4個の炭素原子を有するアルキル基である化合物と、
式(II)で表される第2の化合物であって、式中、R2は、メチル基であり、R3は、6〜15個の炭素原子、好ましくは12〜15個の炭素原子を有するアルキル基である化合物と、任意に、
式(II)で表される第3の化合物であって、式中、R2は、メチル基であり、R3は、16〜20個の炭素原子、好ましくは16〜18個の炭素原子を有するアルキル基である化合物と
の重合によって得られる繰り返し単位を含む、請求項1記載のグラフトコポリマー。 - 前記式(II)で表される第1の化合物と前記式(II)で表される第2の化合物とのモル比が、1:6〜3:1、好ましくは1:4〜3:2、より好ましくは1:2〜2:1の範囲にある、請求項2記載のグラフトコポリマー。
- 前記セグメントAが、少なくとも、
式(I)で表される第1の化合物であって、式中、R1は、水素原子である化合物と、
式(I)で表される第2の化合物であって、式中、R1は、1〜20個の炭素原子、好ましくは1〜10個の炭素原子を有するアルキル基である化合物と
の開環メタセシス重合によって得られる繰り返し単位を含む、請求項1から3までのいずれか1項記載のグラフトコポリマー。 - 前記式(I)で表される第1の化合物と前記式(I)で表される第2の化合物とのモル比が、1:10〜2:1、好ましくは1:7〜1:1、より好ましくは1:4〜1:1の範囲にある、請求項4記載のグラフトコポリマー。
- 前記セグメントAが、50,000g/mol〜300,000g/molの数平均分子量Mnを有し、好ましくは1.5〜2の分散度を有する、請求項1から5までのいずれか1項記載のグラフトコポリマー。
- 前記グラフトコポリマーが、100,000g/mol〜1,000,000g/molの数平均分子量Mnを有し、好ましくは2〜3の分散度を有する、請求項1から6までのいずれか1項記載のグラフトコポリマー。
- 前記グラフトコポリマーが、式(IV):
R1、R2、R3およびR4は、請求項1から8までのいずれか1項に定義されるとおりであり;
R5およびR6は、互いに独立して、水素原子であるか、または1〜19個の炭素原子を有するアルキル基であり、
xは、5〜200、好ましくは10〜150、より好ましくは20〜100であり;
yは、100〜1,500、好ましくは200〜1,200、より好ましくは300〜1,000であり;
zは、100〜1,500、好ましくは500〜1,200、より好ましくは700〜1,000である]で表される化合物である、請求項1から8までのいずれか1項記載のグラフトコポリマー。 - 前記グラフトコポリマーのセグメントBが、20,000g/mol〜1,000,000g/molの全体の数平均分子量Mnを有し、式(II)で表される第1の化合物としてのブチルメタクリレートから誘導された繰り返し単位と、式(II)で表される第2の化合物としてのラウリルメタクリレートから誘導された繰り返し単位とを含み、ブチルメタクリレートから誘導された繰り返し単位と、ラウリルメタクリレートから誘導された繰り返し単位とのモル比が、1:2〜2:1の範囲にあり、
少なくとも前記セグメントAが、前記式(I)で表される第1の化合物であるシクロオクテンと、前記式(I)で表される第2の化合物である3−エチルシクロオクテンとの開環メタセシス重合によって得られる繰り返し単位を含み、シクロオクテンから誘導された繰り返し単位と、3−エチルシクロオクテンから誘導された繰り返し単位とのモル比が、1:4〜1:1の範囲にある、請求項1から9までのいずれか1項記載のグラフトコポリマー。 - 前記グラフトコポリマーのセグメントBが、20,000g/mol〜1,000,000g/molの全体の数平均分子量Mnを有し、式(II)で表される第1の化合物としてのブチルメタクリレートから誘導された繰り返し単位と、式(II)で表される第2の化合物としてのラウリルメタクリレートから誘導された繰り返し単位とを含み、ブチルメタクリレートから誘導された繰り返し単位と、ラウリルメタクリレートから誘導された繰り返し単位とのモル比が、1:2〜2:1の範囲にあり、
少なくとも前記セグメントAが、前記式(I)で表される唯一の化合物であるシクロオクテンの開環メタセシス重合によって得られる繰り返し単位を含む、請求項1から9までのいずれか1項記載のグラフトコポリマー。 - 請求項1から11までのいずれか1項記載のグラフトコポリマーを製造する方法であって、前記方法が、以下の工程:
(a)式(I)の少なくとも1種の化合物と、ハロゲン原子を有する不飽和脂環式化合物とを含む混合物の開環メタセシス重合を行って、ポリマーAを得る工程;
(b)工程(a)で得られたポリマーAの存在下で式(II)の化合物の原子移動ラジカル重合を行って、ポリマーBを得る工程;
(c)工程(b)で得られたポリマーBの水素化を行って、請求項1から11までのいずれか1項記載のコポリマーを得る工程
を含む、方法。 - 基油と、請求項1から11までのいずれか1項記載の少なくとも1種のグラフトコポリマーとを含む潤滑剤組成物。
- 内燃機関におけるオイル添加剤としての、請求項1から11までのいずれか1項記載のグラフトコポリマーの使用。
- 請求項11記載の潤滑剤組成物を含む内燃機関。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201662335898P | 2016-05-13 | 2016-05-13 | |
US62/335,898 | 2016-05-13 | ||
PCT/EP2017/061281 WO2017194654A1 (en) | 2016-05-13 | 2017-05-11 | Graft copolymers based on polyolefin backbone and methacrylate side chains |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2019516828A true JP2019516828A (ja) | 2019-06-20 |
JP6968101B2 JP6968101B2 (ja) | 2021-11-17 |
Family
ID=59054069
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018559793A Active JP6968101B2 (ja) | 2016-05-13 | 2017-05-11 | ポリオレフィン骨格およびメタクリレート側鎖をベースとするグラフトコポリマー |
Country Status (6)
Country | Link |
---|---|
US (1) | US10385288B1 (ja) |
EP (1) | EP3455266B1 (ja) |
JP (1) | JP6968101B2 (ja) |
KR (1) | KR102287600B1 (ja) |
CN (1) | CN109071736B (ja) |
WO (1) | WO2017194654A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109111564B (zh) | 2018-07-20 | 2019-11-19 | 上海交通大学 | 一种支化程度可控的聚烯烃材料的合成方法 |
CN110746529A (zh) * | 2019-11-08 | 2020-02-04 | 铜仁学院 | 一种两性离子聚合物的合成方法 |
CN115023451A (zh) * | 2020-03-25 | 2022-09-06 | 三菱化学株式会社 | 聚合物组合物、润滑油添加剂、粘度指数提高剂、润滑油组合物、聚合物组合物的制造方法、和大分子单体的制造方法 |
CN112876609B (zh) * | 2021-01-18 | 2023-04-07 | 万华化学(四川)有限公司 | 一种聚丁二烯胶乳的制备方法、聚丁二烯胶乳及abs |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002177757A (ja) * | 2000-12-13 | 2002-06-25 | Nippon Zeon Co Ltd | 分散剤及びその使用方法 |
JP2010511065A (ja) * | 2006-11-27 | 2010-04-08 | ユニリーバー・ナームローゼ・ベンノートシヤープ | ブラシ状コポリマー |
JP2010532805A (ja) * | 2007-07-09 | 2010-10-14 | エボニック ローマックス アディティヴス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 燃料消費量を減少させるための櫛形ポリマーの使用 |
Family Cites Families (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3702300A (en) | 1968-12-20 | 1972-11-07 | Lubrizol Corp | Lubricant containing nitrogen-containing ester |
US4788361A (en) | 1987-10-30 | 1988-11-29 | Shell Oil Company | Polymeric viscosity index improver and oil composition comprising the same |
US5002676A (en) | 1989-12-06 | 1991-03-26 | Shell Oil Company | Block copolymers |
FR2701036B1 (fr) | 1993-02-04 | 1995-04-21 | Great Lakes Chemical France | Additif de viscosité stable au cisaillement pour huiles lubrifiantes. |
DE4312715A1 (de) | 1993-04-20 | 1994-10-27 | Roehm Gmbh | Kammpolymere |
WO1995002003A1 (en) | 1993-07-08 | 1995-01-19 | Avery Dennison Corporation | Acrylic-saturated rubber hybrid pressure-sensitive adhesives |
EP0668342B1 (en) | 1994-02-08 | 1999-08-04 | Shell Internationale Researchmaatschappij B.V. | Lubricating base oil preparation process |
DE4431302A1 (de) | 1994-09-02 | 1996-03-07 | Roehm Gmbh | Kammpolymere |
US5460739A (en) | 1994-09-09 | 1995-10-24 | Shell Oil Company | Star polymer viscosity index improver for oil compositions |
US5763548A (en) | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
DE19518786A1 (de) | 1995-05-22 | 1996-11-28 | Roehm Gmbh | Schmierstoffadditive |
US5807937A (en) | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
EP0776959B1 (en) | 1995-11-28 | 2004-10-06 | Shell Internationale Researchmaatschappij B.V. | Process for producing lubricating base oils |
CA2237068C (en) | 1995-12-08 | 2005-07-26 | Exxon Research And Engineering Company | Biodegradable high performance hydrocarbon base oils |
AU735085B2 (en) | 1996-06-12 | 2001-06-28 | Warwick Effect Polymers Limited | Polymerisation catalyst and process |
US5789487A (en) * | 1996-07-10 | 1998-08-04 | Carnegie-Mellon University | Preparation of novel homo- and copolymers using atom transfer radical polymerization |
DE19631170A1 (de) | 1996-08-01 | 1998-02-05 | Basf Ag | Schlagzähe thermoplastische Formmassen |
TW593347B (en) | 1997-03-11 | 2004-06-21 | Univ Carnegie Mellon | Improvements in atom or group transfer radical polymerization |
US6071980A (en) | 1997-08-27 | 2000-06-06 | E. I. Du Pont De Nemours And Company | Atom transfer radical polymerization |
US6090989A (en) | 1997-10-20 | 2000-07-18 | Mobil Oil Corporation | Isoparaffinic lube basestock compositions |
US6059955A (en) | 1998-02-13 | 2000-05-09 | Exxon Research And Engineering Co. | Low viscosity lube basestock |
CA2261458C (en) | 1998-02-18 | 2009-02-10 | The Lubrizol Corporation | Viscosity improvers for lubricating oil compositions |
US6107409A (en) | 1998-05-06 | 2000-08-22 | Bridgestone Corporation | Gels derived from extending grafted comb polymers and polypropylene via a solution synthesis |
US6133210A (en) | 1998-06-30 | 2000-10-17 | The Lubrizol Corporation | Homogeneous additive concentrates for preparing lubricating oil compositions |
US6008164A (en) | 1998-08-04 | 1999-12-28 | Exxon Research And Engineering Company | Lubricant base oil having improved oxidative stability |
US5955405A (en) | 1998-08-10 | 1999-09-21 | Ethyl Corporation | (Meth) acrylate copolymers having excellent low temperature properties |
US6080301A (en) | 1998-09-04 | 2000-06-27 | Exxonmobil Research And Engineering Company | Premium synthetic lubricant base stock having at least 95% non-cyclic isoparaffins |
US6165949A (en) | 1998-09-04 | 2000-12-26 | Exxon Research And Engineering Company | Premium wear resistant lubricant |
US6475960B1 (en) | 1998-09-04 | 2002-11-05 | Exxonmobil Research And Engineering Co. | Premium synthetic lubricants |
US6103099A (en) | 1998-09-04 | 2000-08-15 | Exxon Research And Engineering Company | Production of synthetic lubricant and lubricant base stock without dewaxing |
US6332974B1 (en) | 1998-09-11 | 2001-12-25 | Exxon Research And Engineering Co. | Wide-cut synthetic isoparaffinic lubricating oils |
FR2798136B1 (fr) | 1999-09-08 | 2001-11-16 | Total Raffinage Distribution | Nouvelle huile de base hydrocarbonee pour lubrifiants a indice de viscosite tres eleve |
US7067049B1 (en) | 2000-02-04 | 2006-06-27 | Exxonmobil Oil Corporation | Formulated lubricant oils containing high-performance base oils derived from highly paraffinic hydrocarbons |
WO2006084698A2 (en) | 2005-02-08 | 2006-08-17 | Dsm Ip Assets B.V. | Grafted multi-functional olefin polymer |
DE102005031244A1 (de) | 2005-07-01 | 2007-02-15 | Rohmax Additives Gmbh | Öllösliche Kammpolymere |
DE102007025604A1 (de) | 2007-05-31 | 2008-12-04 | Evonik Rohmax Additives Gmbh | Verbesserte Polymerdispersionen |
WO2014135628A1 (en) * | 2013-03-06 | 2014-09-12 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
-
2017
- 2017-05-11 CN CN201780029469.XA patent/CN109071736B/zh active Active
- 2017-05-11 KR KR1020187035999A patent/KR102287600B1/ko active IP Right Grant
- 2017-05-11 US US16/300,639 patent/US10385288B1/en active Active
- 2017-05-11 WO PCT/EP2017/061281 patent/WO2017194654A1/en unknown
- 2017-05-11 EP EP17729363.6A patent/EP3455266B1/en active Active
- 2017-05-11 JP JP2018559793A patent/JP6968101B2/ja active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002177757A (ja) * | 2000-12-13 | 2002-06-25 | Nippon Zeon Co Ltd | 分散剤及びその使用方法 |
JP2010511065A (ja) * | 2006-11-27 | 2010-04-08 | ユニリーバー・ナームローゼ・ベンノートシヤープ | ブラシ状コポリマー |
JP2010532805A (ja) * | 2007-07-09 | 2010-10-14 | エボニック ローマックス アディティヴス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 燃料消費量を減少させるための櫛形ポリマーの使用 |
Non-Patent Citations (2)
Title |
---|
XU, GUANGJUAN ET AL.: "Functional polyolefins:poly(ethylene)-graft-poly(tert-butyl acrylate) via atom transfer radical poly", MACROMOLECULAR RAPID COMMUNICTION, vol. 33, JPN6020048697, 31 December 2012 (2012-12-31), pages 75 - 79, ISSN: 0004520817 * |
XU, YUEWEN ET AL.: "Synthesis and remarkable efficacy of model polyethylene-graft-poly(methyl methacrylate) copolymers a", MACROMOLECULES, vol. 45, JPN6020048695, 12 December 2012 (2012-12-12), pages 9604 - 9610, XP055394838, ISSN: 0004520818, DOI: 10.1021/ma302187b * |
Also Published As
Publication number | Publication date |
---|---|
KR20190030648A (ko) | 2019-03-22 |
JP6968101B2 (ja) | 2021-11-17 |
EP3455266A1 (en) | 2019-03-20 |
EP3455266B1 (en) | 2020-10-28 |
CN109071736B (zh) | 2021-08-10 |
KR102287600B1 (ko) | 2021-08-11 |
CN109071736A (zh) | 2018-12-21 |
US10385288B1 (en) | 2019-08-20 |
US20190233757A1 (en) | 2019-08-01 |
WO2017194654A1 (en) | 2017-11-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR102549209B1 (ko) | 이미드 관능기를 포함하는 빗살형 중합체 | |
CN109642180B (zh) | 用于改进发动机油配制剂的Noack蒸发损失的梳形聚合物 | |
JP5502730B2 (ja) | 燃料消費量を減少させるための櫛形ポリマーの使用 | |
JP5675660B2 (ja) | スカッフィング耐荷力を改善するためのコームポリマーの使用 | |
KR20150143721A (ko) | 연료 소비를 감소시키기 위한 변속기 오일 제제 | |
JP6968101B2 (ja) | ポリオレフィン骨格およびメタクリレート側鎖をベースとするグラフトコポリマー | |
MX2013000690A (es) | (met) acrilato de polialquilo para mejorar las propiedades del aceite lubricante. | |
KR102408027B1 (ko) | 증진된 탈유화성 성능을 갖는 관능성 폴리알킬 (메트)아크릴레이트 | |
EP4119640B1 (en) | Lubricant additive composition containing polyalkylmethacrylates | |
JP7481814B2 (ja) | せん断抵抗性の改善を示す粘度指数向上剤 | |
WO2023099634A1 (en) | Lubricant compositions | |
WO2023099637A1 (en) | Lubricant compositions | |
WO2023099635A1 (en) | Lubricant compositions | |
WO2024033156A1 (en) | Polyalkyl (meth)acrylate-based polymers with improved low temperature properties | |
KR20220131185A (ko) | 점도 지수 향상제 및 이의 윤활제 조성물 | |
BR102022004901A2 (pt) | Melhorador do índice de viscosidade e composições lubrificantes do mesmo | |
KR20210019956A (ko) | 개선된 전단-저항을 갖는 점도 지수 개선제 | |
JP2023506205A (ja) | 高粘度ポリアクリレートベースフルード |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20181120 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20200304 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20200304 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200310 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20201106 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20201222 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210322 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210607 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210806 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20211011 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20211026 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6968101 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |