JP2009506179A - 油溶性ポリマー - Google Patents
油溶性ポリマー Download PDFInfo
- Publication number
- JP2009506179A JP2009506179A JP2008528452A JP2008528452A JP2009506179A JP 2009506179 A JP2009506179 A JP 2009506179A JP 2008528452 A JP2008528452 A JP 2008528452A JP 2008528452 A JP2008528452 A JP 2008528452A JP 2009506179 A JP2009506179 A JP 2009506179A
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- polymer
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- meth
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- 229920000642 polymer Polymers 0.000 title claims abstract description 158
- -1 pour point improvers Substances 0.000 claims abstract description 83
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 239000003607 modifier Substances 0.000 claims abstract description 10
- 239000002270 dispersing agent Substances 0.000 claims abstract description 6
- 239000004034 viscosity adjusting agent Substances 0.000 claims abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 68
- 239000000178 monomer Substances 0.000 claims description 57
- 239000003921 oil Substances 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 26
- 239000003505 polymerization initiator Substances 0.000 claims description 22
- 239000000654 additive Substances 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- 239000010687 lubricating oil Substances 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 230000000996 additive effect Effects 0.000 claims description 13
- 238000010526 radical polymerization reaction Methods 0.000 claims description 11
- 239000002199 base oil Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000003158 alcohol group Chemical group 0.000 claims description 7
- 239000012634 fragment Substances 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 230000008719 thickening Effects 0.000 abstract description 3
- 235000019198 oils Nutrition 0.000 description 36
- 239000002480 mineral oil Substances 0.000 description 23
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 15
- 235000010446 mineral oil Nutrition 0.000 description 12
- AHLWZBVXSWOPPL-RGYGYFBISA-N 20-deoxy-20-oxophorbol 12-myristate 13-acetate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(C=O)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C AHLWZBVXSWOPPL-RGYGYFBISA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 241001602688 Pama Species 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000009471 action Effects 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- 239000004435 Oxo alcohol Substances 0.000 description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 235000013681 dietary sucrose Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 239000012188 paraffin wax Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 229960004793 sucrose Drugs 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 150000002688 maleic acid derivatives Chemical class 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 3
- 239000010779 crude oil Substances 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
- 230000007423 decrease Effects 0.000 description 3
- 239000003349 gelling agent Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000012705 nitroxide-mediated radical polymerization Methods 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 150000003623 transition metal compounds Chemical class 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XJOUCILNLRXRTF-UHFFFAOYSA-N 1,2,3,4,5,6-hexakis(bromomethyl)benzene Chemical compound BrCC1=C(CBr)C(CBr)=C(CBr)C(CBr)=C1CBr XJOUCILNLRXRTF-UHFFFAOYSA-N 0.000 description 2
- BHIFXIATEXVOQA-UHFFFAOYSA-N 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene Chemical group CC1=C(CBr)C(C)=C(CBr)C(C)=C1CBr BHIFXIATEXVOQA-UHFFFAOYSA-N 0.000 description 2
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- PGMMQIGGQSIEGH-UHFFFAOYSA-N 2-ethenyl-1,3-oxazole Chemical compound C=CC1=NC=CO1 PGMMQIGGQSIEGH-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 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 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 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 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 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
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000012208 gear oil Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000008241 heterogeneous mixture Substances 0.000 description 2
- 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 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000003077 lignite Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
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- 235000000346 sugar Nutrition 0.000 description 2
- 238000012546 transfer Methods 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 1
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 description 1
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 1
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- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 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
- 239000002245 particle Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229920000205 poly(isobutyl methacrylate) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000010675 spruce oil Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- 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
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- 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
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- 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
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
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- 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
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- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
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- 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
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- C10N2040/02—Bearings
Abstract
Description
本発明のポリマーは、低温特性、例えば、−26℃又は−40℃での流動点及びブルックフィールド(Brookfield)−粘度の改善のための卓越した作用を有し得る。
飽和アルコールから誘導される(メタ)アクリレート、フマレート及びマレエート、例えば、2−エチルヘキシル(メタ)アクリレート、ヘプチル(メタ)アクリレート、2−t−ブチルヘプチル(メタ)アクリレート、オクチル(メタ)アクリレート、3−イソプロピルヘプチル(メタ)アクリレート、ノニル(メタ)アクリレート、デシル(メタ)アクリレート、ウンデシル(メタ)アクリレート、5−メチルウンデシル(メタ)アクリレート、ドデシル(メタ)アクリレート、2−メチルドデシル(メタ)アクリレート、トリデシル(メタ)アクリレート、5−メチルトリデシル(メタ)アクリレート、テトラデシル(メタ)アクリレート、ペンタデシル(メタ)アクリレート、ヘキサデシル(メタ)アクリレート、2−メチルヘキサデシル(メタ)アクリレート、ヘプタデシル(メタ)アクリレート、5−イソ−プロピルヘプタデシル(メタ)アクリレート、4−t−ブチルオクタデシル(メタ)アクリレート、5−エチルオクタデシル(メタ)アクリレート、3−イソ−プロピルオクタデシル(メタ)アクリレート、オクタデシル(メタ)アクリレート、ノナデシル(メタ)アクリレート、エイコシル(メタ)アクリレート、セチルエイコシル(メタ)アクリレート、ステアリルエイコシル(メタ)アクリレート、ドコシル(メタ)アクリレート及び/又はエイコシルテトラトリアコンチル(メタ)アクリレート;
シクロアルキル(メタ)アクリレート、例えば、2,4,5−トリ−t−ブチル−3−ビニルシクロヘキシル(メタ)アクリレート、2,3,4,5−テトラ−t−ブチルシクロヘキシル(メタ)アクリレート;
不飽和アルコールから誘導される(メタ)アクリレート、例えば、オレイル(メタ)アクリレート;
シクロアルキル(メタ)アクリレート、例えば、3−ビニルシクロヘキシル(メタ)アクリレート、ボルニル(メタ)アクリレート;及び相応するフマレート及びマレエート。
本発明によるスターポリマーを得るために、この際、有利に、3〜21、特に有利に5〜15及び極めて特に有利に7〜12個の移動可能基を有する重合開始剤を使用する。この重合開始剤は多種自体公知であり、前記の文献に記載されている。
約18〜31個のC−原子を有するn−アルカン:0.7〜1.0%、
18〜31個のC−原子を有する低分枝鎖のアルカン:1.0〜8.0%、
14〜32個のC−原子を有する芳香族体:0.4〜10.7%、
20〜32個のC−原子を有するイソ−及びシクロ−アルカン:60.7〜82.4%、
極性化合物:0.1〜0.8%、
ロス:6.9〜19.4%。
1.多官能重合開始剤の製造
5−アーム−重合開始剤ペンタ(α−ブロモイソブチリル)グルコース及び8−アーム−重合開始剤オクタ(α−ブロモイソブチリル)サッカロースの合成を、文献記載の方法により(M. H. Stenzel-Rosenbaum, T. P. Davis, V. Chen, A. Fane, Macromolecules 34 (2001), 5433)、収率73%又は72%で行なった。構造−確認は、各々1H−NMRを介して行なわれ、これは文献−データ(M. H. Stenzel-Rosenbaum et. al)と一致した。
滴下ロート、サーベル型攪拌器、冷却器、温度計及びN2−供給口を備えた2L入り−反応フラスコから成る装置を使用した。先ず、表1によるモノマー500gをi−オクタン500gと一緒に反応フラスコ中に前以て装入させた。引き続き、CuCl0.6g、CuBr20.01g及び重合開始剤(ペンタ(α−ブロモイソブチリル)グルコース又はオクタ(α−ブロモイソブチリル)サッカロース25〜2.5g、所望のアーム数及び所望の分子量に応じて)を添加した。N2−導入による不活化及び60℃への加熱後に、反応を開始させるために、ペンタメチレンジエチレントリアミン1.1gを添加したが、この際、錯化触媒が不完全にしか溶解していないので、不均一の混合物が生じた。検知可能な発熱反応後に、60°で6時間、次いで70℃で6時間、次いで80°で6時間及び更に90℃で40時間反応させた[スター(ブロック)−PAMAの場合には、90℃で、ブロックコポリマーを5分間以内に滴加し、更に90℃で40時間反応させた]。反応停止は、i−オクタン中CuBr210g/L、ペンタメチレンジエチレントリアミン10g/L及びイルガノックス1010(Irganox(登録商標))5g/Lを含む溶液5mlの添加によって行われた。反応溶液を、Al2O3−カラムを介して、銅塩を除去するために、熱時加圧濾過させた。生成物を3倍容量のメタノールで数回浸出させ、メタノールをデカント除去した。最後に、メタノールを留去させた。溶剤不含で100%粘性〜ゴム状のポリマーを得た。
全ての狭分布の直鎖(ブロック)−PAMA〜比較例7までを、ATRPを介して製造した。銅−錯化モノマーDMAPMAAmを含有する比較例7を、RAFTを介して製造した。
滴下ロート、サーベル型攪拌器、冷却器、温度計及びN2−供給口を備えた2L入り−反応フラスコから成る装置を使用した。先ず、表1によるモノマー600g[直鎖ブロック−PAMA比較例6の場合には、C12/13/15MA564g]を、100N−油400gと一緒に、反応フラスコ中に前以て装入させ、ドライアイス添加及びN2の導入によって不活化させた。引き続き、混合物を攪拌下に95℃に加熱した。加熱過程中、約70℃で、CuBr1,1g及びペンタメチレンジエチレントリアミン1.4gを添加させたが、この際、錯化触媒が不完全にしか溶解しなかったので、不均一の混合物が得られた。95℃の所定温度の達成後に、反応を開始させるために、エチルブロモイソブチレート(所望の分子量に応じて7.5g〜1.5g)を添加した。95℃で6時間反応させた[比較例6の場合には、95℃で2時間反応させ、DMAEMA36gを5分間以内に滴加して、更に4時間95℃で反応させた]。引き続き、銅塩の除去のために、混合物を熱時加圧濾過させた(ザイツ(Seitz)T100 10μmデプスフィルター)。60%の粘性溶液を得た。
比較例7は、滴下ロート、サーベル型攪拌器、冷却器、温度計及びN2−供給口を備えた2L入り−反応フラスコ中で、RAFTを介して製造した。そのために、C12/13/14/15MA540gを、クミルジチオベンゾエート2.71g、t−ブチルペルオクトエート1.14g及び100N−油400gと一緒に反応フラスコ中に前以て装入させ、ドライアイス添加及びN2の導入によって不活化させた。引き続き、混合物を85℃に加熱した。5時間後に、DMAPMAAm60gを滴加した。更に2.5時間後に、t−ブチルペルオクトエート0.60gを添加し、反応混合物を85℃で1晩攪拌した。60%の帯赤色粘性溶液を得た。
表1によるモノマー600g及びn−ドデシルメルカプタン(所望の分子量に応じて、20g〜2g)を混合する。このモノマー/調整剤−混合物44.4gを100N−油400gと一緒に、サーベル型攪拌器、冷却器、温度計、供給ポンプ及びN2−供給口を備えた2L入り−反応フラスコ中に充填させる。この装置を不活化させ、油浴を併用して100℃に加熱する。総残量のモノマー/調整剤−混合物555.6gに、t−ブチルペルオクトエート1.4gを加える。反応フラスコ中の混合物が100℃の温度に達した時に、t−ブチルペルオクトエート0.25gを添加し、同時に、モノマー/調整剤/重合開始剤−混合物の供給をポンプにより開始する。供給は、100℃で210分間の時間に渡って一様に行われる。供給の2時間後に、再びt−ブチルペルオクトエート1.2gを添加し、100℃で更に2時間攪拌する。60%の澄明な溶液を得た。
ポリマーの質量平均分子量Mw及び多分散度指数PDIを、GPCによって測定した(表1)。測定は、テトラヒドロフラン中で、35℃で、≧25個の標準(Polymer Standards Service 又はPolymer Laboratories)の1組からのポリメチルメタクリレート−検量線に対して行われ、そのMピークは対数的に一様に5・106〜2・102g/モルの範囲にわたって分布されていた。6個のカラム(Polymer Standards Service SDV 100Å/2xSDV LXL/2xSDV 100Å/Shodex KF-800D)を含む組合せを使用した。シグナル受信のために、RI−検出器(Agilent 1100 Series)を使用した。
100N−キャリヤーオイル中の溶液としてのみ存在する慣例の直鎖PAMA及び狭分布の直鎖(ブロック)−PAMAの場合には、組成の際に、100N−キャリヤーオイルは無視され、各々、組成油−秤量に付加された。
表2は、類似のPSSI(DIN 51350により(部6、円錐ローラー軸受20時間)、ASTM D5621により(超音波40分間)又はDIN 51382により(ボッシュ−ポンプ(Bosch-Pumpe)30サイクル)及び類似VI(ASTM D2270)で、慣例的に製造された直鎖PAMA(1.6≦PDI≦2.7)及び狭分布の直鎖PAMA(1.3≦PDI≦1.5)に比較して、本発明によるPAMA−スターの場合には、100℃KV100=14.0mm2/s(ASTM D445)での運動粘度に必要なポリマー濃度が、100N−油で著しく減少していることを実証する。
摩擦変性剤としての本発明によるPAMA−ブロックスターの特性も検査した(表4)。そのために、ポリマーを、150N−ベースオイル(BP Enerpar 11)で、KV120=9.2mm2/sに調整した。引き続き、組成物を、摩擦計(Mini Traction Machine 3, PCS Instruments)により、0.005〜2.5m/sの範囲の速度で摩擦測定をした。この際、30Nの負荷(0.93GPa最高ヘルツ接触圧に相応する)及び滑り/ロール−率50%で、温度は120℃で一定であった。ディスクは、Typ AISI 52100の鋼鉄製(直径40.0mm、粗面度rms(平均平方根(root mean square))25〜30nm、ロックウエル−C−硬度63、弾性係数207GPa)であり、ボール(直径19.0mm、粗面度rms10〜13nm、ロックウエル−C−硬度58〜65、弾性係数207Gpa)も同様であった。摩擦試験の結果として、ストライベック(Stribeck)−曲線が得られ、これから摩擦係数fを10mm/sで調べた。
PAMA−スターの、例えば、粒子不含の油圧応用組成物中での使用可能性の試験のために、無水の濾過性を、ISO 13357−2により、1バール圧で5μm−フィルターによって試験した(表6)。この試験で、段階1は、濾過の早期データからの投影濾過性F1≦100%を示し、かつ段階2は濾過の全経過に渡る濾過性F2≦100%を示す。
酸化安定性の試験(表7)のために、酸化試験を、CEC L−48−A−00(B)により(160℃、192時間、通気5L/h)VII−不含の、PPD−及びD/I−パケット−含有のAPI−群I GO−組成物中5.3%のポリマー溶液で実施し、相対的変化△KV100relを測定した。酸化を行った後に、付加的に、n−ヘキサン−不溶性成分Is(不溶物(insolubles))を懸濁液から重量計測法で測定した。慣例的に製造された直鎖PAMA(比較例11)との比較は、PAMA−スター例2の驚異的な利点を示した。
表8は、類似PSSIのポリマー試料(DIN 51350(部6、円錐ローラー軸受20時間)により又はASTM D5621(超音波40分間)により)について、例えば、本発明によるPAMA−ブロックスター例8及び例9の場合には、ATRPを介して製造された直鎖PAMA比較例3及び比較例5に比較して、KV100=14.0mm2/sに必要な150N−油中のポリマー濃度を著しく減少させることを新たに実証する。この際、付加的に、外へ回転したMMA−ブロックを有するPAMA−ブロックスターのブロック状構造は、粘度を、低下された温度(40℃)での可逆的会合粘稠化を介して非常に高く上昇させようとすることが殊に注目に値する(表8)。このことは、例7及び8の場合に、比較例3及び比較例5と比較して、合目的に僅少なVIに反映する。しかし、剪断は、PSSI40℃>PSSI100℃≡PSSIという観察で検知可能な、40℃で所与の会合効果を再び破壊する。しかし、典型的には、直鎖PAMAについては、PSSI40℃=PSSI100℃〜PSSI40℃≦PSSI100℃が当てはまる。
Claims (33)
- ポリマーの質量に対して、1種以上の式(I):
- ポリマーは、ISO 13357−2による投影濾過性(段階1)に対して、少なくとも90%の濾過性を有する、請求項1に記載のポリマー。
- ポリマーは、ISO 13357−2による濾過の全経過(段階2)に対して、少なくとも70%の濾過性を有する、請求項1又は2に記載のポリマー。
- スターポリマーの中心は、高々50個の炭素原子を有する、請求項1から3までのいずれか1項に記載のポリマー。
- スターポリマーは5〜12個のアームを有する、請求項1から4までのいずれか1項に記載のポリマー。
- スターポリマーは、質量平均分子量Mwを25000〜150000g/モルの範囲で有する、請求項1から5までのいずれか1項に記載のポリマー。
- スターポリマーは、多分散度Mw/Mnを1.0〜1.3の範囲で有する、請求項1から6までのいずれか1項に記載のポリマー。
- ポリマーは、分散性モノマー(III)から誘導される繰返し単位30質量%までを有する、請求項1から8までのいずれか1項に記載のポリマー。
- 分散性モノマーは、アルコールR7−OHをベースとする分散性(メタ)アクリレート又はアミンR7−NR8−Hをベースとする(メタ)アクリルアミドであり、R7は、独立して、少なくとも1個のヘテロ原子を有する2〜200個の炭素原子を包含する基であり、かつR8は、独立して、水素又は1〜20個の炭素原子を有する基である、請求項9に記載のポリマー。
- 基R7は、少なくとも1個の式 −OR8又は−NR8R8の基を包含し、ここで、基R8は、独立して、水素又は1〜20個の炭素原子を有する基である、請求項10に記載のポリマー。
- 基R7は、高々10個の炭素原子を包含する、請求項10又は11に記載のポリマー。
- スターポリマーは、少なくとも2個のブロックを有する、請求項1から12までのいずれか1項に記載のポリマー。
- スターポリマーは、少なくとも1個の親油性及び1個の疎油性ブロックを有する、請求項13に記載のポリマー。
- 少なくとも1個の疎油性ブロックは、ブロックの質量に対して、1種以上の式(II)のエチレン系不飽和エステル化合物、分散性モノマー(III)及び/又は群(IV)による他のコモノマーから誘導される繰返し単位少なくとも50質量%を有する、請求項14に記載のポリマー。
- ポリマーは、疎油性ブロック内に、3個以上の整数の断片長さを有する疎油性断片を有する、請求項14又は15に記載のポリマー。
- 疎油性ブロックは、粘度指数−上昇性スターポリマーの中心付近に配置されている、請求項14から16までのいずれか1項に記載のポリマー。
- 疎油性ブロックは、粘度指数−低下性スターポリマーのアームの末端付近に配置されている、請求項14から16までのいずれか1項に記載のポリマー。
- ポリマーは、中心付近に、1種以上の式(II)のエチレン系不飽和エステル化合物の高含量及び/又は他の式(IV)のコモノマーを包含する疎油性ブロック、及び分散性モノマー(III)から誘導される疎油性ブロックをアームの末端付近に有する、請求項17又は18に記載のポリマー。
- 請求項1から19までのいずれか1項に記載のポリマーを製造する方法において、ポリマーを、制御重合によって、多官能重合開始剤から出発して製造することを特徴とする方法。
- ポリマーを、制御ラジカル重合によって、多官能重合開始剤から出発して製造する、請求項20に記載の方法。
- 重合は、油及び/又は非極性溶剤の存在下で行なわれる、請求項20又は21に記載の方法。
- 請求項1から19までのいずれか1項に記載のスターポリマーを含有する油組成物。
- 油組成物は、請求項1から19までのいずれか1項に記載のスターポリマー1〜25質量%を包含する、請求項23に記載の油組成物。
- ASTM D5621(超音波40分間)によるPSSIは、25以下である、請求項23又は24に記載の油組成物。
- DIN D51350 6部(円錐ローラー軸受20時間)によるPSSIは、50以下である、請求項23又は24に記載の油組成物。
- 粘度指数は0〜300の範囲で合目的に調整可能である、請求項23から26までのいずれか1項に記載の油組成物。
- 油組成物は、潤滑油組成物である、請求項23から27までのいずれか1項に記載の油組成物。
- API群I、II、III、IV及び/又は群Vのベースオイルを包含する、請求項28に記載の潤滑油組成物。
- 潤滑油組成物は、請求項1から19までのいずれか1項に記載のスターポリマーではない少なくとも1種の付加的な添加剤を包含する、請求項29に記載の潤滑油組成物。
- 付加的な添加剤は、粘度指数改善剤、流動点改善剤、分散剤及び/又は摩擦変性剤である、請求項30に記載の潤滑油組成物。
- 添加剤は、アルコール基中に1〜30個の炭素原子を有する直鎖ポリアルキル(メタ)アクリレートに基づいている、請求項30又は31に記載の潤滑油組成物。
- 請求項1から19までのいずれか1項に記載のスターポリマーの、粘性変性剤、流動点改善剤、分散剤及び/又は摩擦変性剤としての使用。
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JP2010535870A (ja) * | 2007-08-06 | 2010-11-25 | 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 | 抗疲労添加剤としてのエステル基含有ポリマーの使用 |
JP2013536879A (ja) * | 2010-08-31 | 2013-09-26 | ザ ルブリゾル コーポレイション | 星型ポリマーおよびその潤滑組成物 |
WO2014017557A1 (ja) * | 2012-07-24 | 2014-01-30 | Jx日鉱日石エネルギー株式会社 | エンジン油組成物 |
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JP2015013957A (ja) * | 2013-07-05 | 2015-01-22 | Jx日鉱日石エネルギー株式会社 | ポリ(メタ)アクリレート系粘度指数向上剤、並びに該粘度指数向上剤を含有する潤滑油添加剤及び潤滑油組成物 |
JPWO2016043195A1 (ja) * | 2014-09-17 | 2017-06-01 | 株式会社日本触媒 | 粘度指数向上剤及びその製造方法、並びに潤滑油組成物 |
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Also Published As
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US20100167970A1 (en) | 2010-07-01 |
JP5452921B2 (ja) | 2014-03-26 |
CA2617554A1 (en) | 2007-03-08 |
BRPI0615243A2 (pt) | 2011-05-10 |
WO2007025837A1 (de) | 2007-03-08 |
CA2617554C (en) | 2014-02-18 |
EP1919961A1 (de) | 2008-05-14 |
KR20080049723A (ko) | 2008-06-04 |
US8163682B2 (en) | 2012-04-24 |
MX2008002129A (es) | 2008-04-22 |
KR101301835B1 (ko) | 2013-09-12 |
DE102005041528A1 (de) | 2007-03-01 |
CN101189268A (zh) | 2008-05-28 |
EP1919961B1 (de) | 2014-06-04 |
CN101189268B (zh) | 2010-07-14 |
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