JPH11506391A - 選択的水素化ポリマーから得られる分散剤および分散剤粘度指数向上剤 - Google Patents
選択的水素化ポリマーから得られる分散剤および分散剤粘度指数向上剤Info
- Publication number
- JPH11506391A JPH11506391A JP9500448A JP50044897A JPH11506391A JP H11506391 A JPH11506391 A JP H11506391A JP 9500448 A JP9500448 A JP 9500448A JP 50044897 A JP50044897 A JP 50044897A JP H11506391 A JPH11506391 A JP H11506391A
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- conjugated diene
- formula
- hydrogen
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 256
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 179
- 150000001993 dienes Chemical class 0.000 claims abstract description 213
- 229920001577 copolymer Polymers 0.000 claims abstract description 102
- 238000000034 method Methods 0.000 claims abstract description 64
- 239000000463 material Substances 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 58
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000012530 fluid Substances 0.000 claims abstract description 25
- 230000001050 lubricating effect Effects 0.000 claims abstract description 16
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 96
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 70
- 238000006116 polymerization reaction Methods 0.000 claims description 60
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 59
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 45
- -1 Benzyl hydrogen Chemical compound 0.000 claims description 31
- 229920005604 random copolymer Polymers 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000000524 functional group Chemical group 0.000 claims description 15
- 229920000768 polyamine Polymers 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 8
- 125000001743 benzylic group Chemical group 0.000 claims description 5
- 229920005605 branched copolymer Polymers 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims 1
- 238000007306 functionalization reaction Methods 0.000 abstract description 25
- 125000003118 aryl group Chemical group 0.000 abstract description 13
- 239000003921 oil Substances 0.000 abstract description 13
- 239000002480 mineral oil Substances 0.000 abstract description 9
- 239000012141 concentrate Substances 0.000 abstract description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 5
- 239000010688 mineral lubricating oil Substances 0.000 abstract description 2
- 239000010689 synthetic lubricating oil Substances 0.000 abstract description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 121
- 239000003054 catalyst Substances 0.000 description 67
- 239000000243 solution Substances 0.000 description 58
- 239000007788 liquid Substances 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 47
- 239000000178 monomer Substances 0.000 description 35
- 150000003440 styrenes Chemical class 0.000 description 34
- 229920001400 block copolymer Polymers 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 239000003638 chemical reducing agent Substances 0.000 description 30
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 28
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 28
- 229910052740 iodine Inorganic materials 0.000 description 28
- 239000011630 iodine Substances 0.000 description 28
- 238000007792 addition Methods 0.000 description 27
- 239000005062 Polybutadiene Substances 0.000 description 26
- 229920002857 polybutadiene Polymers 0.000 description 26
- 150000003623 transition metal compounds Chemical class 0.000 description 23
- 150000001336 alkenes Chemical class 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 19
- 230000002829 reductive effect Effects 0.000 description 18
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
- 229920001971 elastomer Polymers 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000654 additive Substances 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 13
- 150000001450 anions Chemical class 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 229920001195 polyisoprene Polymers 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 12
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 238000009826 distribution Methods 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 11
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 10
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 10
- 239000003607 modifier Substances 0.000 description 10
- 229920001083 polybutene Polymers 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 239000000806 elastomer Substances 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- 230000000717 retained effect Effects 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 229910017052 cobalt Inorganic materials 0.000 description 8
- 239000010941 cobalt Substances 0.000 description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 8
- 239000000306 component Substances 0.000 description 8
- 238000007796 conventional method Methods 0.000 description 8
- 239000007822 coupling agent Substances 0.000 description 8
- 239000000446 fuel Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 229920013639 polyalphaolefin Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- 229920002943 EPDM rubber Polymers 0.000 description 7
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 150000002496 iodine Chemical class 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000005060 rubber Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 235000008504 concentrate Nutrition 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 5
- 238000006596 Alder-ene reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229920002449 FKM Polymers 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- BYDROKITEOVIPQ-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical class C=CC=C.CC(=C)C=C.CC(=C)C=C BYDROKITEOVIPQ-UHFFFAOYSA-N 0.000 description 5
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 230000002708 enhancing effect Effects 0.000 description 5
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- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
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- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 4
- YHHHHJCAVQSFMJ-FNORWQNLSA-N (3e)-deca-1,3-diene Chemical compound CCCCCC\C=C\C=C YHHHHJCAVQSFMJ-FNORWQNLSA-N 0.000 description 4
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 4
- MDKXFHZSHLHFLN-UHFFFAOYSA-N alumanylidynecobalt Chemical compound [Al].[Co] MDKXFHZSHLHFLN-UHFFFAOYSA-N 0.000 description 4
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
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- 125000002524 organometallic group Chemical group 0.000 description 4
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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- HIVLIDXXXODBCB-UHFFFAOYSA-N 2-methylidenebut-3-enylbenzene Chemical compound C=CC(=C)CC1=CC=CC=C1 HIVLIDXXXODBCB-UHFFFAOYSA-N 0.000 description 3
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 125000000129 anionic group Chemical group 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- KENMWXODTSEHKF-UHFFFAOYSA-N deca-3,5-diene Chemical compound CCCCC=CC=CCC KENMWXODTSEHKF-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
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- RMWHYWJWLBDARH-WJDMQLPWSA-N (2e,4e)-deca-2,4-diene Chemical compound CCCCC\C=C\C=C\C RMWHYWJWLBDARH-WJDMQLPWSA-N 0.000 description 2
- PCCCQOGUVCNYOI-FNORWQNLSA-N (3e)-2,3-dimethylpenta-1,3-diene Chemical compound C\C=C(/C)C(C)=C PCCCQOGUVCNYOI-FNORWQNLSA-N 0.000 description 2
- RMWHYWJWLBDARH-UHFFFAOYSA-N (E,E)-2,4-decadiene Natural products CCCCCC=CC=CC RMWHYWJWLBDARH-UHFFFAOYSA-N 0.000 description 2
- IJCPWQYDBDFHBH-UHFFFAOYSA-N 1-buta-1,3-dien-2-yl-4-methylbenzene Chemical compound CC1=CC=C(C(=C)C=C)C=C1 IJCPWQYDBDFHBH-UHFFFAOYSA-N 0.000 description 2
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- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- QTOJRHLRJFVPJN-UHFFFAOYSA-L nickel(2+);diphenoxide Chemical compound C=1C=CC=CC=1O[Ni]OC1=CC=CC=C1 QTOJRHLRJFVPJN-UHFFFAOYSA-L 0.000 description 1
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- KHMYONNPZWOTKW-UHFFFAOYSA-N pent-1-enylbenzene Chemical compound CCCC=CC1=CC=CC=C1 KHMYONNPZWOTKW-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
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- 229920000647 polyepoxide Polymers 0.000 description 1
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- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- ZYBHSWXEWOPHBJ-UHFFFAOYSA-N potassium;propan-2-ylbenzene Chemical compound [K+].C[C-](C)C1=CC=CC=C1 ZYBHSWXEWOPHBJ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- QLUMLEDLZDMGDW-UHFFFAOYSA-N sodium;1h-naphthalen-1-ide Chemical compound [Na+].[C-]1=CC=CC2=CC=CC=C21 QLUMLEDLZDMGDW-UHFFFAOYSA-N 0.000 description 1
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- 238000004611 spectroscopical analysis Methods 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- QQXSEZVCKAEYQJ-UHFFFAOYSA-N tetraethylgermanium Chemical compound CC[Ge](CC)(CC)CC QQXSEZVCKAEYQJ-UHFFFAOYSA-N 0.000 description 1
- ZRLCXMPFXYVHGS-UHFFFAOYSA-N tetramethylgermane Chemical compound C[Ge](C)(C)C ZRLCXMPFXYVHGS-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
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- C10L1/00—Liquid carbonaceous fuels
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- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
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- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
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- C08F8/00—Chemical modification by after-treatment
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- C08F8/00—Chemical modification by after-treatment
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.環置換スチレンと少なくとも1種の共役ジエンとのコポリマーを含んでな る、流体の分散性または粘度特性を改質するための分散剤物質であって、 (A)前記環置換スチレンは、少なくとも1つのベンジル水素および式 (式中、n=1〜5、そしてRAおよびRBはそれぞれ水素またはヒドロカルビル 基である)を有し、そして (B)前記少なくとも1種の共役ジエンは、下記(a)または(b)であり、 (a)少なくとも5つの炭素原子および次式を有する共役ジエン (式中、R1−R6はそれぞれ水素またはヒドロカルビル基であるが、ただし、R1 −R6の少なくとも1つがヒドロカルビル基であることを条件とする)、ただし 、重合の後に式(1)中の重合された共役ジエン中の不飽和が式 (式中、RI、RII、RIIIおよびRIVはそれぞれ水素あるいはヒドロカルビル基 であるが、ただし、RIおよびRIIの両方がヒドロカルビル基であるか、または RIIIおよびRIVの両方がヒドロカルビル基であるかのいずれかであることを条 件とする)を有することを条件とする;または (b)少なくとも4つの炭素原子および次式を有する共役ジエン (式中、R7−R12はそれぞれ水素あるいはヒドロカルビル基である)、ただし 、重合の後に式(3)の重合された共役ジエン中の不飽和が式 (式中、RV、RVI、RVIIおよびRVIIIはそれぞれ水素またはヒドロカルビル基 であるが、ただし、RVまたはRVIが水素であり、RVIIまたはRVIIIが水素であ り、RV、RVI、RVIIおよびRVIIIの少なくとも1つがヒドロカルビル基である ことを条件とする)を有することを条件とする;そして (C)前記コポリマーは 前記コポリマーを選択的に水素化して選択的水素化コポリマーを与えること、 および 前記選択的水素化コポリマーを官能化して、少なくとも1つの極性官能基を有 する官能化コポリマーを提供すること を含んでなる方法により官能化されている、 前記の分散剤物質。 2.前記環置換スチレンおよび前記共役ジエンが、ランダムコポリマーとして 重合されている、請求項1に記載の分散剤物質。 3.前記環置換スチレンおよび前記共役ジエンが、枝分れまたは星状枝分れコ ポリマーとして重合されている、請求項1に記載の分散剤物質。 4.前記コポリマーが、少なくとも2,000の分子量を有する、請求項1に 記載の分散剤物質。 5.前記環置換スチレンが、前記ポリマーに約0.5重量%〜約25重量%の 量で含まれ、前記共役ジエンが、前記ポリマーに約75重量%〜約99.5重量 %の量で含まれる、請求項1に記載の分散剤物質。 6.式(1)または(3)の共役ジエンが、イソプレン、1,3ブタジエン、 あるいはこれらの混合物からなる、請求項1に記載の分散剤物質。 7.前記官能化段階が、前記選択的水素化コポリマーをハロゲン化してハロゲ ン化コポリマーを提供することを含む、請求項1に記載の分散剤物質。 8.前記官能化段階が、さらに、前記臭化コポリマーをモノアミン、ポリアミ ン、あるいはこれらの混合物と反応させることを含む、請求項7に記載の分散剤 物質。 9.改質された分散性または粘度特性を有する流体を与えるのに十分な量の分 散剤物質を、流体と混合することを含んでなる、流体の分散性または粘度特性を 改質する方法であって、 前記分散剤物質が、環置換スチレンと少なくとも1種の共役ジエンとのコポリ マーを含んでなり、 (A)前記環置換スチレンは、少なくとも1つのベンジル水素および式 (式中、n=1〜5、そしてRAおよびRBはそれぞれ水素またはヒドロカルビル 基である)を有し、そして (B)前記少なくとも1種の共役ジエンは、下記(a)または(b)であり、 (a)少なくとも5つの炭素原子および次式を有する共役ジエン (式中、R1−R6はそれぞれ水素またはヒドロカルビル基であるが、ただし、R1 −R6の少なくとも1つがヒドロカルビル基であることを条件とする)、ただし 、重合の後に式(1)中の重合された共役ジエン中の不飽和が式 (式中、RI、RII、RIIIおよびRIVはそれぞれ水素あるいはヒドロカルビル基 であるが、ただし、RIおよびRIIの両方がヒドロカルビル基であるか、または RIIIおよびRIVの両方がヒドロカルビル基であるかのいずれかであることを条 件とする)を有することを条件とする;または (b)少なくとも4つの炭素原子および次式を有する共役ジエン (式中、R7−R12はそれぞれ水素あるいはヒドロカルビル基である)、ただし 、重合の後に式(3)の重合された共役ジエン中の不飽和が式 (式中、RV、RVI、RVIIおよびRVIIIはそれぞれ水素またはヒドロカルビル基 であるが、ただし、RVまたはRVIが水素であり、RVIIまたはRVIIIが水素であ り、RV、RVI、RVIIおよびRVIIIの少なくと も1つがヒドロカルビル基であることを条件とする)を有することを条件とする ;そして (C)前記コポリマーは 前記コポリマーを選択的に水素化して選択的水素化コポリマーを与えること、 および 前記選択的水素化コポリマーを官能化して、少なくとも1つの極性官能基を有 する官能化コポリマーを提供すること を含んでなる方法により官能化されている、 前記の方法。 10.流体、および 環置換スチレンと少なくとも1種の共役ジエンとのコポリマーを含んでなる分 散剤物質 を含んでなる、改質された分散性と粘度特性を有する潤滑流体であって、 (A)前記環置換スチレンは、少なくとも1つのベンジル水素および式 (式中、n=1〜5、そしてRAおよびRBはそれぞれ水素またはヒドロカルビル 基である)を有し、そして (B)前記少なくとも1種の共役ジエンは、下記(a)または(b)であり、 (a)少なくとも5つの炭素原子および次式を有する共役ジエン (式中、R1−R6はそれぞれ水素またはヒドロカルビル基であるが、ただし、R1 −R6の少なくとも1つがヒドロカルビル基であることを条件とする)、ただし 、重合の後に式(1)中の重合された共役ジエン中の不飽和が式 (式中、RI、RII、RIIIおよびRIVはそれぞれ水素あるいはヒドロカルビル基 であるが、ただし、RIおよびRIIの両方がヒドロカルビル基であるか、または RIIIおよびRIVの両方がヒドロカルビル基であるかのいずれかであることを条 件とする)を有することを条件とする;または (b)少なくとも4つの炭素原子および次式を有する共役ジエン (式中、R7−R12はそれぞれ水素あるいはヒドロカルビル基である)、ただし 、重合の後に式(3)の重合された共役ジエン中の不飽和が式 (式中、RV、RVI、RVIIおよびRVIIIはそれぞれ水素またはヒドロカルビル基 であるが、ただし、RVまたはRVIが水素であり、RVIIまたはRVIIIが水素であ り、RV、RVI、RVIIおよびRVIIIの少なくとも1つがヒドロカルビル基である ことを条件とする)を有することを条件とする;そして (C)前記コポリマーは 前記コポリマーを選択的に水素化して選択的水素化コポリマーを与えること、 および 前記選択的水素化コポリマーを官能化して、少なくとも1つの極性官能基を有 する官能化コポリマーを提供すること を含んでなる方法により官能化されている、 前記の潤滑流体。
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US08/476,016 US5637783A (en) | 1990-01-16 | 1995-06-07 | Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers |
US476,016 | 1995-06-07 | ||
PCT/US1996/004064 WO1996040845A1 (en) | 1995-06-07 | 1996-03-26 | Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers |
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Cited By (3)
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JP2010059374A (ja) * | 2008-09-06 | 2010-03-18 | Tonengeneral Sekiyu Kk | 潤滑油組成物 |
JP5263480B2 (ja) * | 2005-12-14 | 2013-08-14 | 株式会社クラレ | ブロック共重合体およびその水素添加物 |
WO2014142001A1 (ja) * | 2013-03-11 | 2014-09-18 | 株式会社クラレ | 粘度指数向上剤、その製造方法及び油組成物 |
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US6248702B1 (en) | 1990-01-16 | 2001-06-19 | Mobil Oil Corporation | Dispersant and dispersant viscosity index improvers from selectively hydrogenated aryl-substituted olefin containing diene copolymers |
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- 1996-03-26 KR KR1019970708895A patent/KR100396351B1/ko not_active Expired - Fee Related
- 1996-03-26 BR BR9608553-3A patent/BR9608553A/pt not_active Application Discontinuation
- 1996-03-26 RU RU98100232/04A patent/RU2180680C2/ru not_active IP Right Cessation
- 1996-03-26 CA CA002221461A patent/CA2221461A1/en not_active Abandoned
- 1996-03-26 JP JP9500448A patent/JPH11506391A/ja not_active Ceased
- 1996-03-26 CN CN96194447A patent/CN1186510A/zh active Pending
- 1996-06-29 TW TW085107866A patent/TW420623B/zh not_active IP Right Cessation
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Cited By (4)
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JP5263480B2 (ja) * | 2005-12-14 | 2013-08-14 | 株式会社クラレ | ブロック共重合体およびその水素添加物 |
JP2010059374A (ja) * | 2008-09-06 | 2010-03-18 | Tonengeneral Sekiyu Kk | 潤滑油組成物 |
WO2014142001A1 (ja) * | 2013-03-11 | 2014-09-18 | 株式会社クラレ | 粘度指数向上剤、その製造方法及び油組成物 |
JP5671658B1 (ja) * | 2013-03-11 | 2015-02-18 | 株式会社クラレ | 粘度指数向上剤、その製造方法及び油組成物 |
Also Published As
Publication number | Publication date |
---|---|
NO975630D0 (no) | 1997-12-04 |
KR100396351B1 (ko) | 2003-12-18 |
NO975630L (no) | 1998-01-27 |
CN1186510A (zh) | 1998-07-01 |
AU5372396A (en) | 1996-12-30 |
KR19990022415A (ko) | 1999-03-25 |
TW420623B (en) | 2001-02-01 |
BR9608553A (pt) | 2000-10-31 |
CA2221461A1 (en) | 1996-12-19 |
WO1996040845A1 (en) | 1996-12-19 |
RU2180680C2 (ru) | 2002-03-20 |
AU690842B2 (en) | 1998-04-30 |
US5637783A (en) | 1997-06-10 |
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