JP6545813B2 - 潤滑油用粘度調整剤、潤滑油用添加剤組成物および潤滑油組成物 - Google Patents
潤滑油用粘度調整剤、潤滑油用添加剤組成物および潤滑油組成物 Download PDFInfo
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- JP6545813B2 JP6545813B2 JP2017550297A JP2017550297A JP6545813B2 JP 6545813 B2 JP6545813 B2 JP 6545813B2 JP 2017550297 A JP2017550297 A JP 2017550297A JP 2017550297 A JP2017550297 A JP 2017550297A JP 6545813 B2 JP6545813 B2 JP 6545813B2
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- JP
- Japan
- Prior art keywords
- lubricating oil
- group
- ethylene
- olefin
- cyclopentadienyl
- 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.)
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- 239000010687 lubricating oil Substances 0.000 title claims description 236
- 239000000203 mixture Substances 0.000 title claims description 128
- 239000004034 viscosity adjusting agent Substances 0.000 title claims description 95
- 239000000654 additive Substances 0.000 title claims description 40
- 230000000996 additive effect Effects 0.000 title claims description 27
- -1 dimethylsilyl Chemical group 0.000 claims description 198
- 239000004711 α-olefin Substances 0.000 claims description 185
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 118
- 239000005977 Ethylene Substances 0.000 claims description 118
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 95
- 238000006116 polymerization reaction Methods 0.000 claims description 86
- 238000000034 method Methods 0.000 claims description 75
- 229920005989 resin Polymers 0.000 claims description 73
- 239000011347 resin Substances 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 55
- 239000003921 oil Substances 0.000 claims description 49
- 229920000098 polyolefin Polymers 0.000 claims description 43
- 229920001577 copolymer Polymers 0.000 claims description 41
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 40
- 229910052710 silicon Inorganic materials 0.000 claims description 40
- 150000003623 transition metal compounds Chemical class 0.000 claims description 40
- 239000010703 silicon Substances 0.000 claims description 34
- 230000000737 periodic effect Effects 0.000 claims description 33
- 150000001336 alkenes Chemical class 0.000 claims description 32
- 239000002480 mineral oil Substances 0.000 claims description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 22
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 22
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 20
- 238000005227 gel permeation chromatography Methods 0.000 claims description 20
- 235000010446 mineral oil Nutrition 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000003446 ligand Substances 0.000 claims description 17
- 238000002844 melting Methods 0.000 claims description 16
- 230000008018 melting Effects 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 230000000994 depressogenic effect Effects 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 150000002430 hydrocarbons Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 238000007334 copolymerization reaction Methods 0.000 claims description 11
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000003607 modifier Substances 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- 150000008282 halocarbons Chemical group 0.000 claims description 7
- 239000002685 polymerization catalyst Substances 0.000 claims description 7
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052735 hafnium Inorganic materials 0.000 claims description 6
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001993 dienes Chemical class 0.000 claims description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 4
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 63
- 229920000642 polymer Polymers 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 125000001183 hydrocarbyl group Chemical group 0.000 description 41
- 230000000052 comparative effect Effects 0.000 description 39
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- 238000003860 storage Methods 0.000 description 27
- 229920005672 polyolefin resin Polymers 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000005259 measurement Methods 0.000 description 23
- 238000004458 analytical method Methods 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 18
- 239000002270 dispersing agent Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 13
- 238000009826 distribution Methods 0.000 description 13
- 150000008040 ionic compounds Chemical class 0.000 description 13
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 12
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 12
- 238000005191 phase separation Methods 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- 239000000446 fuel Substances 0.000 description 11
- 229920013639 polyalphaolefin Polymers 0.000 description 11
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 10
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 10
- 230000007423 decrease Effects 0.000 description 10
- 150000002736 metal compounds Chemical group 0.000 description 10
- 125000005234 alkyl aluminium group Chemical group 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 9
- 239000003599 detergent Substances 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 230000006872 improvement Effects 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 8
- 239000000314 lubricant Substances 0.000 description 8
- 239000010705 motor oil Substances 0.000 description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 239000010700 blended lubricating oil Substances 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical compound [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 150000003624 transition metals Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- SZKKRCSOSQAJDE-UHFFFAOYSA-N Schradan Chemical group CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C SZKKRCSOSQAJDE-UHFFFAOYSA-N 0.000 description 6
- 238000013329 compounding Methods 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 6
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- ROMKCELWQXNFHN-UHFFFAOYSA-L [Cl-].[Cl-].CC1=C(C=2CC3=CC(=C(C=C3C=2C=C1C(C)(C)C)C(C)(C)C)C)[Hf+2] Chemical compound [Cl-].[Cl-].CC1=C(C=2CC3=CC(=C(C=C3C=2C=C1C(C)(C)C)C(C)(C)C)C)[Hf+2] ROMKCELWQXNFHN-UHFFFAOYSA-L 0.000 description 5
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- 150000001721 carbon Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 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 4
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- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 4
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 4
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- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 3
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- IDASTKMEQGPVRR-UHFFFAOYSA-N cyclopenta-1,3-diene;zirconium(2+) Chemical compound [Zr+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 IDASTKMEQGPVRR-UHFFFAOYSA-N 0.000 description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- 239000007788 liquid Substances 0.000 description 3
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- 229910052744 lithium Inorganic materials 0.000 description 3
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- WNVQCJNZEDLILP-UHFFFAOYSA-N dimethyl(oxo)tin Chemical compound C[Sn](C)=O WNVQCJNZEDLILP-UHFFFAOYSA-N 0.000 description 1
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- TURVSLXVJYZFII-UHFFFAOYSA-N zinc;1,2,3,4,5-pentafluorobenzene-6-ide Chemical compound [Zn+2].FC1=[C-]C(F)=C(F)C(F)=C1F.FC1=[C-]C(F)=C(F)C(F)=C1F TURVSLXVJYZFII-UHFFFAOYSA-N 0.000 description 1
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Description
樹脂(α)を含む潤滑油用粘度調整剤であって、前記樹脂(α)が、下記要件(I)および(II)を満たし、かつ、主鎖および側鎖から構成され下記要件(i)および(ii)を満たすグラフト型オレフィン系重合体[R1]を含む、潤滑油用粘度調整剤。
(i)前記主鎖が、エチレンと、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンとの共重合体からなり、前記エチレンから導かれる構造単位が74〜86mol%の範囲にある。
(ii)前記側鎖が、エチレンと、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンとの共重合体からなり、前記エチレンから導かれる構造単位が30〜65mol%の範囲にある。
(I)示差走査熱量分析(DSC)によって測定された融点(Tm)が−20〜100℃の範囲にある。
(II)135℃のデカリン中で測定した極限粘度[η]が0.5〜2.5dl/gの範囲にある。
前記樹脂(α)が、下記要件(III)をさらに満たす、[1]に記載の潤滑油用粘度調整剤。
(III)エチレンから導かれる構造単位の割合が全構造単位に対し40〜85mol%、炭素原子数3〜12のα−オレフィンから導かれる構造単位の割合が全構造単位に対し15〜60mol%(ただしエチレンから導かれる構造単位と、炭素原子数3〜12のα−オレフィンから導かれる構造単位との合計を100mol%とする)の範囲にある。
前記樹脂(α)が、エチレンから導かれる構造単位とプロピレンから導かれる構造単位とからなる、[1]または[2]に記載の潤滑油用粘度調整剤。
JIS K7112に準拠し密度勾配管法により測定した樹脂(α)の密度が850〜880kg/m3の範囲にある、[1]〜[3]のいずれかに記載の潤滑油用粘度調整剤。
前記グラフト型オレフィン系重合体[R1]がさらに下記要件(iii)を満たす、[1]〜[4]のいずれかに記載の潤滑油用粘度調整剤。
(iii)前記主鎖が、重量平均分子量が70000〜400000の範囲にあるエチレン・α−オレフィン共重合体に由来する。
前記グラフト型オレフィン系重合体[R1]がさらに下記要件(iv)を満たす、[1]〜[5]のいずれかに記載の潤滑油用粘度調整剤。
(iv)前記側鎖が、重量平均分子量(Mw)が1000〜70000の範囲のエチレン・α−オレフィン共重合体に由来する。
下記(A)および(B)の工程を含む、[1]〜[6]のいずれかに記載の潤滑油用粘度調整剤の製造方法。
(A)周期表第4族の遷移金属化合物[A]を含むオレフィン重合用触媒の存在下で、エチレンと、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンとを共重合し、末端不飽和エチレン・α−オレフィン共重合体を製造する工程。
(B)周期表第4族の遷移金属化合物[B]を含むオレフィン重合用触媒の存在下で、工程(A)で製造される末端不飽和エチレン・α−オレフィン共重合体と、エチレンと、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンとを共重合し、樹脂(α)を製造する工程。
前記工程(A)で製造される末端不飽和エチレン・α−オレフィン共重合体が、エチレンから導かれる構造単位が30〜65mol%の範囲にあり、かつ、ゲルパーミエーションクロマトグラフィーで測定した重量平均分子量(Mw)が1000〜70000の範囲にある、[7]に記載の潤滑油用粘度調整剤の製造方法。
前記周期表第4族の遷移金属化合物[A]が、ジメチルシリルビスインデニル骨格を有する配位子を含む周期表第4族の遷移金属化合物である、[7]または[8]に記載の潤滑油用粘度調整剤の製造方法。
前記周期表第4族の遷移金属化合物[B]が、下記一般式[B]であらわされる架橋メタロセン化合物である、[7]〜[9]のいずれかに記載の潤滑油用粘度調整剤の製造方法。
[11]
前記工程(B)が重合温度90℃以上の溶液重合プロセスである、[7]〜[10]のいずれか一項に記載の潤滑油用粘度調整剤の製造方法。
[1]〜[6]のいずれかに記載の潤滑油用粘度調整剤1〜50質量部と、油(B)50〜99質量部と(ただし、潤滑油用粘度調整剤と、油(B)の合計を100質量部とする)を含む、潤滑油添加剤組成物。
[1]〜[6]のいずれかに記載の潤滑油用粘度調整剤0.1〜5質量部と、潤滑油基材(BB)95〜99.9質量部と(ただし、潤滑油用粘度調整剤と、潤滑油基材(BB)の合計を100質量部とする)を含む、潤滑油組成物。
さらに、流動点降下剤(C)を、該潤滑油組成物100質量%中に、0.05〜5質量%の量で含む、[13]に記載の潤滑油組成物。
前記潤滑油基材(BB)が鉱物油である、[13]または[14]に記載の潤滑油組成物。
前記潤滑油基材(BB)が合成油である、[13]または[14]に記載の潤滑油組成物。
本発明の潤滑油用粘度調整剤は、樹脂(α)を含み、樹脂(α)は、グラフト型オレフィン系重合体[R1]を含む。以下に各構成成分につき詳述する。
本発明の潤滑油用粘度調整剤に含まれる、樹脂(α)は、主鎖および側鎖から構成されるグラフト型オレフィン系重合体[R1]を含み、要件(I)および(II)を満たす。
グラフト型オレフィン系重合体[R1]の主鎖はエチレン・α−オレフィン共重合体からなり、グラフト型オレフィン系重合体[R1]において、潤滑油組成物として要求される剪断安定性や低温特性を担う部位となる。そのような特性を担保するために、グラフト型オレフィン系重合体[R1]の主鎖は、エチレンから導かれる構造単位と、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンから導かれる構造単位とからなる。
グラフト型オレフィン系重合体[R1]の側鎖が、エチレンから導かれる構造単位と、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンから導かれる構造単位とからなり、エチレンから導かれる構造単位が好ましくは30〜65mol%のエチレン・α−オレフィン共重合体からなる。エチレンから導かれる構造単位は、より好ましくは35〜60mol%の範囲である。また、α−オレフィンから導かれる構造単位の割合は側鎖に含まれる全構造単位に対し35〜70mol%、好ましくは40〜65mol%の範囲である。
グラフト型オレフィン系重合体[R1]の主鎖を構成する上記エチレン・α−オレフィン共重合体の重量平均分子量が70000〜400000の範囲にある。好ましくは80000〜300000、より好ましくは90000〜250000の範囲にある。上記重量平均分子量はゲルパーミエーションクロマトグラフィー(GPC)によって求められるポリスチレン換算の重量平均分子量に相当する。
側鎖が、重量平均分子量が1000〜70000であるエチレン・α−オレフィン共重合体に由来する。上記重量平均分子量は、好ましくは2000〜50000、さらに好ましくは3000〜40000、特に好ましくは4000〜20000の範囲である。
示差走査熱量分析(DSC)によって測定された融点(Tm)が−20〜100℃の範囲にある。好ましくは−10〜80℃の範囲にあり、より好ましくは0〜60℃の範囲にある。上記上限値以下にあることにより低温下における貯蔵安定性に優れ、上記下限値以上にあることにより低温での粘度特性に優れる。
135℃のデカリン中で測定した極限粘度[η]が0.5〜2.5dl/gの範囲にある。好ましくは0.55〜2.0dl/gであり、より好ましくは0.6〜1.8dl/gである。上記範囲にあることで剪断安定性に優れる。
エチレンから導かれる構造単位の割合が全構造単位に対し40〜85mol%、炭素原子数3〜12のα−オレフィンから導かれる構造単位の割合が全構造単位に対し15〜60mol%(ただしエチレンから導かれる構造単位と、炭素原子数3〜12のα−オレフィンから導かれる構造単位との合計を100mol%とする)の範囲にある。エチレンから導かれる構造単位の割合はより好ましくは45〜85mol%、特に好ましくは50〜85mol%、炭素原子数3〜12のα−オレフィンから導かれる構造単位の割合はより好ましくは15〜55mol%、特に好ましくは15〜50mol%である。
ゲルパーミエーションクロマトグラフィー(GPC)で測定される重量平均分子量(Mw)が70000〜400000の範囲にある。より好ましくは80000〜300000の範囲、さらにより好ましくは100000〜250000の範囲にある。前述のとおり、本発明において、重量平均分子量という用語は、GPCで測定したポリスチレン換算の重量平均分子量を示す。GPCの測定方法は実施例の項で詳述する。
JIS K7112に準拠し密度勾配管法により測定した密度が850〜880kg/m3の範囲にある。より好ましくは850〜877kg/m3の範囲、特に好ましくは850〜874kg/m3の範囲にある。上記範囲にあることは低温粘度を低減できる点において好ましい。
本発明の潤滑油用粘度調整剤は、下記(A)および(B)の工程を含む製造方法により樹脂(α)を製造する工程を含む方法にて製造可能である。
以下、(A)、(B)の工程について順により詳しく説明する。
工程(A)は、周期表第4族の遷移金属化合物[A]の存在下で、末端不飽和エチレン・α−オレフィン共重合体を製造する工程であり、前述したグラフト型オレフィン系重合体[R1]の側鎖の原料となる。この側鎖の原料は非晶性であり、融点を有しない。
工程(B)は、周期表第4族の遷移金属化合物[B]の存在下で、工程(A)で製造される末端不飽和エチレン・α−オレフィン共重合体(具体的には、片末端にビニル基をもつエチレン・α−オレフィン共重合体)と、エチレンと、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンとを共重合し、樹脂(α)を製造する工程である。
以下、本発明で用いられうる架橋メタロセン化合物[B]の化学構造上の特徴について説明する。
式[B]中、R1、R2、R3およびR4はそれぞれ独立に水素原子、炭化水素基、ケイ素含有基またはケイ素含有基以外のヘテロ原子含有基を示すものであり、末端ビニルエチレン・α−オレフィン共重合体を良好に取り込む構造として、R1、R2、R3およびR4は全て水素原子であるか、またはR1、R2、R3およびR4のいずれか一つ以上がメチル基であり残りは水素原子である構造が特に好ましい。
式[B]中、R5、R8、R9およびR12はそれぞれ独立に水素原子、炭化水素基、ケイ素含有基またはケイ素含有基以外のヘテロ原子含有基を示し、水素原子、炭化水素基またはケイ素含有基が好ましい。R6およびR11は水素原子、炭化水素基、ケイ素含有基およびケイ素含有基以外のヘテロ原子含有基から選ばれる同一の原子または同一の基であり、水素原子、炭化水素基およびケイ素含有基が好ましく;R7およびR10は水素原子、炭化水素基、ケイ素含有基およびケイ素含有基以外のヘテロ原子含有基から選ばれる同一の原子または同一の基であり、水素原子、炭化水素基およびケイ素含有基が好ましく;R6およびR7は互いに結合して環を形成していてもよく、R10およびR11は互いに結合して環を形成していてもよく;ただし、"R6、R7、R10およびR11が全て水素原子であること"はない。
式[B]中、R13およびR14はそれぞれ独立にアリール基を示し、Y1は炭素原子またはケイ素原子を示す。オレフィン重合体の製造方法において重要な点は、架橋部の架橋原子Y1に、互いに同一でも異なっていてもよいアリール(aryl)基であるR13およびR14を有することである。製造上の容易性から、R13およびR14は互いに同一であることが好ましい。
式[B]中、Qはハロゲン原子、炭化水素基、ハロゲン化炭化水素基、炭素原子数4〜10の中性の共役もしくは非共役ジエン、アニオン配位子または孤立電子対で配位可能な中性配位子を示し、jは1〜4の整数を示し、jが2以上の整数の場合は複数あるQはそれぞれ同一でも異なっていてもよい。
以下に架橋型メタロセン化合物[B]の具体例を式[II]〜[VI]に示す。なお、例示化合物中、オクタメチルオクタヒドロジベンゾフルオレニルとは式[II]で示される構造の化合物に由来する基を指し、オクタメチルテトラヒドロジシクロペンタフルオレニルとは式[III]で示される構造の化合物に由来する基を指し、ジベンゾフルオレニルとは式[IV]で示される構造の化合物に由来する基を指し、1,1',3,6,8,8'−ヘキサメチル−2,7−ジヒドロジシクロペンタフルオレニルとは式[V]で示される構造の化合物に由来する基を指し、1,3,3',6,6',8−ヘキサメチル−2,7−ジヒドロジシクロペンタフルオレニルとは式[VI]で示される構造の化合物に由来する基を指す。
ジフェニルメチレン(シクロペンタジエニル)(2,7−ジtert−ブチルフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(3,6−ジtert−ブチルフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(オクタメチルオクタヒドロジベンゾフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(オクタメチルテトラヒドロジシクロペンタフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(ジベンゾフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(1,1',3,6,8,8'−ヘキサメチル−2,7−ジヒドロジシクロペンタフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(1,3,3',6,6',8−ヘキサメチル−2,7−ジヒドロジシクロペンタフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(2,7−ジフェニル−3,6−ジtert−ブチルフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(2,7−ジメチル−3,6−ジtert−ブチルフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(2,7−(トリメチルフェニル)−3,6−ジtert−ブチルフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(2,7−(ジメチルフェニル)−3,6−ジtert−ブチルフルオレニル)ハフニウムジクロリド、ジフェニルメチレン(シクロペンタジエニル)(2,3,6,7−テトラtert−ブチルフルオレニル)ハフニウムジクロリド、
本発明にかかる樹脂(α)の製造方法では、上述した工程(A),(B)においてオレフィン重合用触媒として用いられる遷移金属化合物[A]および架橋メタロセン化合物[B]と共に、後述する化合物[C]を用いることが好ましい。
本発明で用いられる[C1]有機金属化合物として、具体的には下記の一般式(C1−a)で表わされる有機アルミニウム化合物、一般式(C1−b)で表わされる周期表第1族金属とアルミニウムとの錯アルキル化物、および一般式(C1−c)で表わされる周期表第2族または第12族金属のジアルキル化合物が挙げられる。なお、[C1]有機金属化合物には、後述する[C2]有機アルミニウムオキシ化合物は含まないものとする。
上記一般式(C1−a)で表わされる有機アルミニウム化合物としては、次のような一般式(C−1a−1)〜(C−1a−4)で表わされる化合物を例示できる。
トリイソプロピルアルミニウム、トリイソブチルアルミニウム、トリsec−ブチルアルミニウム、トリtert−ブチルアルミニウム、トリ2−メチルブチルアルミニウム、トリ3−メチルブチルアルミニウム、トリ2−メチルペンチルアルミニウム、トリ3−メチルペンチルアルミニウム、トリ4−メチルペンチルアルミニウム、トリ2−メチルヘキシルアルミニウム、トリ3−メチルヘキシルアルミニウム、トリ2−エチルヘキシルアルミニウムなどのトリ分岐鎖アルキルアルミニウム;
トリシクロヘキシルアルミニウム、トリシクロオクチルアルミニウムなどのトリシクロアルキルアルミニウム;
トリフェニルアルミニウム、トリトリルアルミニウムなどのトリアリールアルミニウム;
ジイソブチルアルミニウムハイドライドなどのジアルキルアルミニウムハイドライド;
(i−C4H9)xAly(C5H10)z(式中、x、y、zは正の数であり、z≧2xである。)などで表されるトリイソプレニルアルミニウムなどのトリアルケニルアルミニウム;
イソブチルアルミニウムメトキシド、イソブチルアルミニウムエトキシド、イソブチルアルミニウムイソプロポキシドなどのアルキルアルミニウムアルコキシド;
ジメチルアルミニウムメトキシド、ジエチルアルミニウムエトキシド、ジブチルアルミニウムブトキシドなどのジアルキルアルミニウムアルコキシド;
エチルアルミニウムセスキエトキシド、ブチルアルミニウムセスキブトキシドなどのアルキルアルミニウムセスキアルコキシド;
Ra 2.5Al(ORb)0.5で表される平均組成を有する部分的にアルコキシ化されたアルキルアルミニウム(式中、RaおよびRbは、互いに同一でも異なっていてもよく、炭素原子数が1〜15、好ましくは1〜4の炭化水素基を示す);
ジエチルアルミニウムフェノキシド、ジエチルアルミニウム(2,6−ジ−t−ブチル−4−メチルフェノキシド)、エチルアルミニウムビス(2,6−ジ−t−ブチル−4−メチルフェノキシド)、ジイソブチルアルミニウム(2,6−ジ−t−ブチル−4−メチルフェノキシド)、イソブチルアルミニウムビス(2,6−ジ−t−ブチル−4−メチルフェノキシド)などのジアルキルアルミニウムアリーロキシド;
ジメチルアルミニウムクロリド、ジエチルアルミニウムクロリド、ジブチルアルミニウムクロリド、ジエチルアルミニウムブロミド、ジイソブチルアルミニウムクロリドなどのジアルキルアルミニウムハライド;
エチルアルミニウムセスキクロリド、ブチルアルミニウムセスキクロリド、エチルアルミニウムセスキブロミドなどのアルキルアルミニウムセスキハライド;
エチルアルミニウムジクロリド、プロピルアルミニウムジクロリド、ブチルアルミニウムジブロミドなどのアルキルアルミニウムジハライドなどの部分的にハロゲン化されたアルキルアルミニウム;
ジエチルアルミニウムヒドリド、ジブチルアルミニウムヒドリドなどのジアルキルアルミニウムヒドリド;
エチルアルミニウムジヒドリド、プロピルアルミニウムジヒドリドなどのアルキルアルミニウムジヒドリドなどその他の部分的に水素化されたアルキルアルミニウム;
エチルアルミニウムエトキシクロリド、ブチルアルミニウムブトキシクロリド、エチルアルミニウムエトキシブロミドなどの部分的にアルコキシ化およびハロゲン化されたアルキルアルミニウムなどを挙げることができる。
本発明で用いられる[C2]有機アルミニウムオキシ化合物は、従来公知のアルミノキサンであってもよく、また特開平2−78687号公報に例示されているようなベンゼン不溶性の有機アルミニウムオキシ化合物であってもよい。[C2]有機アルミニウムオキシ化合物としては、具体的には、メチルアルミノキサン、エチルアルミノキサン、イソブチルアルミノキサン等が挙げられる。
上記一般式(III)で表されるボロンを含んだ有機アルミニウムオキシ化合物は、下記一般式(IV)で表されるアルキルボロン酸と、有機アルミニウム化合物とを、不活性ガス雰囲気下に不活性溶媒中で、−80℃〜室温の温度で1分〜24時間反応させることにより製造できる。
上記一般式(IV)で表されるアルキルボロン酸の具体的な例としては、メチルボロン酸、エチルボロン酸、イソプロピルボロン酸、n−プロピルボロン酸、n−ブチルボロン酸、イソブチルボロン酸、n−ヘキシルボロン酸、シクロヘキシルボロン酸、フェニルボロン酸、3,5−ジフルオロフェニルボロン酸、ペンタフルオロフェニルボロン酸、3,5−ビス(トリフルオロメチル)フェニルボロン酸などが挙げられる。これらの中では、メチルボロン酸、n−ブチルボロン酸、イソブチルボロン酸、3,5−ジフルオロフェニルボロン酸、ペンタフルオロフェニルボロン酸が好ましい。これらは1種単独でまたは2種以上組み合わせて用いられる。
本発明で用いられる、遷移金属化合物[A]または架橋メタロセン化合物[B]と反応してイオン対を形成する化合物[C3](以下、「イオン化イオン性化合物」という。)としては、特開平1−501950号公報、特開平1−502036号公報、特開平3−179005号公報、特開平3−179006号公報、特開平3−207703号公報、特開平3−207704号公報、USP−5321106号などに記載されたルイス酸、イオン性化合物、ボラン化合物およびカルボラン化合物などを挙げることができる。さらに、ヘテロポリ化合物およびイソポリ化合物も挙げることができる。
イオン化イオン性化合物(化合物[C3])の例であるボラン化合物として具体的には、例えば、デカボラン;
ビス〔トリ(n−ブチル)アンモニウム〕ノナボレート、ビス〔トリ(n−ブチル)アンモニウム〕デカボレート、ビス〔トリ(n−ブチル)アンモニウム〕ウンデカボレート、ビス〔トリ(n−ブチル)アンモニウム〕ドデカボレート、ビス〔トリ(n−ブチル)アンモニウム〕デカクロロデカボレート、ビス〔トリ(n−ブチル)アンモニウム〕ドデカクロロドデカボレートなどのアニオンの塩;
トリ(n−ブチル)アンモニウムビス(ドデカハイドライドドデカボレート)コバルト酸塩(III)、ビス〔トリ(n−ブチル)アンモニウム〕ビス(ドデカハイドライドドデカボレート)ニッケル酸塩(III)などの金属ボランアニオンの塩などが挙げられる。
トリ(n−ブチル)アンモニウムビス(ノナハイドライド−1,3−ジカルバノナボレート)コバルト酸塩(III)、トリ(n−ブチル)アンモニウムビス(ウンデカハイドライド−7,8−ジカルバウンデカボレート)鉄酸塩(III)、トリ(n−ブチル)アンモニウムビス(ウンデカハイドライド−7,8−ジカルバウンデカボレート)コバルト酸塩(III)、トリ(n−ブチル)アンモニウムビス(ウンデカハイドライド−7,8−ジカルバウンデカボレート)ニッケル酸塩(III)、トリ(n−ブチル)アンモニウムビス(ウンデカハイドライド−7,8−ジカルバウンデカボレート)銅酸塩(III)、トリ(n−ブチル)アンモニウムビス(ウンデカハイドライド−7,8−ジカルバウンデカボレート)金酸塩(III)、トリ(n−ブチル)アンモニウムビス(ノナハイドライド−7,8−ジメチル−7,8−ジカルバウンデカボレート)鉄酸塩(III)、トリ(n−ブチル)アンモニウムビス(ノナハイドライド−7,8−ジメチル−7,8−ジカルバウンデカボレート)クロム酸塩(III)、トリ(n−ブチル)アンモニウムビス(トリブロモオクタハイドライド−7,8−ジカルバウンデカボレート)コバルト酸塩(III)、トリス〔トリ(n−ブチル)アンモニウム〕ビス(ウンデカハイドライド−7−カルバウンデカボレート)クロム酸塩(III)、ビス〔トリ(n−ブチル)アンモニウム〕ビス(ウンデカハイドライド−7−カルバウンデカボレート)マンガン酸塩(IV)、ビス〔トリ(n−ブチル)アンモニウム〕ビス(ウンデカハイドライド−7−カルバウンデカボレート)コバルト酸塩(III)、ビス〔トリ(n−ブチル)アンモニウム〕ビス(ウンデカハイドライド−7−カルバウンデカボレート)ニッケル酸塩(IV)などの金属カルボランアニオンの塩などが挙げられる。
本発明の潤滑油用粘度調整剤の製造方法は、工程(A)および(B)に加え、必要に応じて、工程(B)で生成する重合体を回収する工程(C)を含んでも良い。本工程は、工程(A)および(B)において用いられる有機溶剤を分離してポリマーを取り出し製品形態に変換する工程であり、溶媒濃縮、押し出し脱気、ペレタイズ等の既存のポリオレフィン樹脂を製造する過程であれば特段制限はない。
本発明の潤滑油添加剤組成物は、本発明の潤滑油用粘度調整剤1〜50質量部と、油(B)50〜99質量部(ただし、潤滑油用粘度調整剤と、油(B)の合計を100質量部とする)を含む。好ましくは潤滑油用粘度調整剤を2〜40質量部、油(B)を60〜98質量部の範囲で、より好ましくは潤滑油用粘度調整剤を3〜30質量部、油(B)を70〜97質量部の範囲で含む。
本発明の潤滑油組成物は、本発明の潤滑油用粘度調整剤0.1〜5質量部と、潤滑油基剤(BB)95〜99.9質量部と、(ただし、潤滑油用粘度調整剤と、潤滑油基材(BB)の合計を100質量部とする)を含む。潤滑油用粘度調整剤は、好ましくは0.2〜4質量部、より好ましくは0.4〜3質量部、さらに好ましくは0.6〜2質量部、潤滑油基材(BB)は好ましくは96〜99.8質量部、より好ましくは97〜99.6質量部、さらに好ましくは98〜99.4質量部の割合で含有される。潤滑油用粘度調整剤は、一種を単独で用いてもよく、複数種を組み合わせて用いてもよい。
実施例または比較例で製造する樹脂を、インジウム標準にて較正したSII社製示差走査型熱量計(X−DSC7000)を用いて、DSC測定を行う。
極限粘度[η]は、デカリン溶媒を用いて、135℃で測定した。具体的には、重合パウダー、ペレットまたは樹脂塊約20mgをデカリン15mlに溶解し、135℃のオイルバス中で比粘度ηspを測定した。このデカリン溶液にデカリン溶媒を5ml追加して希釈後、同様にして比粘度ηspを測定した。この希釈操作をさらに2回繰り返し、濃度(C)を0に外挿した時のηsp/Cの値を極限粘度として求めた(下式参照)。
[密度]
実施例または比較例で製造または使用する樹脂の密度は、JIS K7112に記載の方法に従い、測定する。
実施例または比較例で製造または使用する共重合体の重量平均分子量および分子量分布は、以下の方法により測定する。
実施例または比較例で製造または使用する共重合体30mgをo−ジクロロベンゼン20mlに145℃で溶解した後、その溶液を孔径が1.0μmの焼結フィルターで濾過したものを分析試料とする。
ゲルパーミエーションクロマトグラフィー(GPC)を用いて重量平均分子量(Mw)、数平均分子量(Mn)および分子量分布曲線を求める。計算はポリスチレン換算で行う。求めた重量平均分子量(Mw)、数平均分子量(Mn)からMw/Mnを算出する。
ゲル浸透クロマトグラフHLC−8321 GPC/HT型(東ソー社製)
(解析装置)
データ処理ソフトEmpower2(Waters社、登録商標)
(測定条件)
カラム:TSKgel GMH6−HTを2本、およびTSKgel GMH6−HTLを2本(いずれも直径7.5mm×長さ30cm、東ソー社)
カラム温度:140℃
移動相:o−ジクロロベンゼン(0.025%BHT含有)
検出器:示差屈折率計
流速:1mL/分
試料濃度:0.15%(w/v)
注入量:0.4mL
サンプリング時間間隔:1秒
カラム較正:単分散ポリスチレン(東ソー社)
分子量換算:PS換算/標品換算法
(樹脂(α)におけるグラフト型オレフィン系重合体[R1]の含有量([R1]/(α)(wt%)))
GPC測定結果から、樹脂(α)におけるグラフト型オレフィン系重合体[R1]の含有量を以下の方法で算出した。
ここで、S(G1)、S(G4)はそれぞれ(G1)、(G4)の面積である。
実施例または比較例で製造または使用する共重合体のエチレンおよびα−オレフィン由来の構造単位(モル%)については、13C−NMRスペクトルの解析により求める。
ブルカーバイオスピン社製AVANCEIII500CryoProbe Prodigy型核磁気共鳴装置
(測定条件)
測定核:13C(125MHz)、測定モード:シングルパルスプロトンブロードバンドデカップリング、パルス幅:45°(5.00μ秒)、ポイント数:64k、測定範囲:250ppm(−55〜195ppm)、繰り返し時間:5.5秒、積算回数:512回、測定溶媒:オルトジクロロベンゼン/ベンゼン−d6(4/1 v/v)、試料濃度:ca.60mg/0.6mL、測定温度:120℃、ウインドウ関数:exponential(BF:1.0Hz)、ケミカルシフト基準:ベンゼン−d6(128.0ppm)。
実施例または比較例で製造または使用する共重合体の不飽和末端量および末端ビニル量については、1H−NMRスペクトルの解析により求める。
日本電子製ECX400P型核磁気共鳴装置、測定核:1H(400MHz)
(測定条件)
1H(400MHz)、測定モード:シングルパルス、パルス幅:45°(5.25μ秒)、ポイント数:32k、測定範囲:20ppm(−4〜16ppm)、繰り返し時間:5.5秒、積算回数:512回、測定溶媒:1,1,2,2,−テトラクロロエタン−d2、試料濃度:ca.60mg/0.6mL、測定温度:120℃、ウインドウ関数:exponential(BF:0.12Hz)、ケミカルシフト基準:1,1,2,2,−テトラクロロエタン(5.91ppm)。
[鉱物油配合系潤滑油組成物の調製]
実施例および比較例で得られた潤滑油用粘度調整剤を含むエンジンオイル(潤滑油組成物)を調製する。該潤滑油組成物は下記の成分を含む:
APIグループIII 基油 89.65〜90.95(重量%)
添加剤* 8.15(質量%)
流動点降下剤(ポリメタクリレート)0.3(質量%)
共重合体 0.6〜1.9(表4に示すとおり)(質量%)
合計 100.0(質量%)
注:* 添加剤=CaおよびNaの過塩基性清浄剤、N含有分散剤、アミン性[aminic]およびフェノール性の抗酸化剤、ジアルキルジチオリン酸亜鉛類、摩擦調整剤、および消泡剤を含む従来のエンジン潤滑油パッケージ。
APIグループIVオイル(PAO)74.58〜75.89(質量%)
APIグループIII 基油 15.0(質量%)
添加剤* 8.15(質量%)
流動点降下剤(ポリメタクリレート)0.3(質量%)
共重合体 0.66〜1.97(表4に示すとおり)(質量%)
合計 100.0(質量%)
注:* 添加剤=CaおよびNaの過塩基性清浄剤、N含有分散剤、アミン性[aminic]およびフェノール性の抗酸化剤、ジアルキルジチオリン酸亜鉛類、摩擦調整剤、および消泡剤を含む従来のエンジン潤滑油パッケージ。
実施例または比較例で調製する鉱物油配合系潤滑油組成物のSSIを、JPI−5S−29−88規定を参考にした超音波法で測定する。潤滑油組成物に超音波を照射し、照射前後の動粘度低下率からSSIを測定する。SSIは潤滑油中の共重合体成分が摺動下でせん断力を受け分子鎖が切断することによる動粘度の低下の尺度である。SSIが大きい値であるほど、動粘度の低下が大きいことを示す。
US−300TCVP型超音波せん断安定度試験装置(プリムテック製)
(測定条件)
発振周波数:10KHz
試験温度:40℃
照射ホーン位置:液面下2mm
(測定方法)
試料容器に試料を30ml採取し、4.2Vの出力電圧により超音波を30分間照射する。超音波照射前後の試料油の100℃における動粘度を測定し、以下に示す式により、SSIを求める。
Vo:超音波照射前の100℃動粘度(mm2/s)
Vs:超音波照射後の100℃動粘度(mm2/s)
Vb:潤滑油用粘度調整剤の成分量を0質量%として調整したエンジンオイル(潤滑油組成物)の100℃動粘度(mm2/s)
一般的に、SSIが小さい潤滑油組成物は、動粘度の低下は相対的に小さくなるが、配合比率に占める粘度調整剤の割合が相対的に高くなる傾向を示す。一方、SSIが大きい潤滑油組成物は、動粘度の低下は相対的に大きいが、配合比率に占める粘度調整剤の割合が相対的に低くなる傾向を示す。
実施例または比較例で調製する潤滑油組成物の100℃における動粘度を、ASTM D446に基づき測定する。
実施例または比較例で調製する鉱物油配合系潤滑油組成物のCCS粘度(−30℃)を、ASTM D2602に基づいて測定する。CCS粘度は、クランク軸における低温での摺動性(始動性)の評価に用いられる。値が小さい程、潤滑油の低温粘度(低温特性)が優れることを示す。
実施例または比較例で調製する合成油配合系潤滑油組成物のMR粘度(−40℃)を、ASTM D4648に基づいて測定する。
実施例または比較例で調製する潤滑油組成物の低温貯蔵特性を評価する。
2・・・(相分離があるが、程度が小さい)
3・・・(相分離があるが、程度がやや小さい)
4・・・(相分離があり、程度がやや大きい)
5・・・(相分離があり、程度が大きい)
これら結果を、表4に併せて示す。
工程(A):末端不飽和エチレン・α−オレフィン共重合体(M−1)の製造
触媒として使用したジメチルシリルビス(2−メチル−4−フェニルインデニル)ジルコニウムジクロリドは特許第3737134号に開示されている方法に従って合成した。
触媒として使用した下記式で示される化合物(1)は公知の方法によって合成した。
末端不飽和エチレン・α−オレフィン共重合体(M−1)の仕込み量を48.0gにして工程(B)を実施したこと以外は実施例1と同様にオレフィン系樹脂を製造した。オレフィン系樹脂(α−2)を54.5g得た。オレフィン系樹脂(α−2)の分析結果を表3に示す。このオレフィン系樹脂(α−2)を潤滑油用粘度調整剤として評価した結果を表4に示す。
工程(A):末端不飽和エチレン・α−オレフィン共重合体(M−2)の製造
充分に窒素置換した内容積2Lのガラス製反応器に、トルエン1.0Lを入れたのち、100℃に昇温した。そこに600rpmで重合器内部を撹拌しながら、エチレンおよびプロピレンをそれぞれ129リットル/hrおよび109リットル/hrで連続的に供給し、液相および気相を飽和させた。引き続きエチレンおよびプロピレンを連続的に供給した状態で、メチルアルミノキサン(PMAOとも記す)のトルエン溶液(アルミ原子濃度:1.5mol/L)を2.0mL、ついでジメチルシリルビス(2−メチル−4−フィニルインデニル)ジルコニウムジクロリドのトルエン溶液(0.010mol/L)を3.0mL(0.030mmol)加え、常圧下、100℃で5分間重合を行った。重合の停止は少量のイソブタノールを添加することにより行った。得られた重合反応液を、希塩酸で洗浄し、分液して得られた有機層を濃縮した。さらに得られた濃縮液を80℃にて10時間減圧乾燥することにより、末端不飽和エチレン・α−オレフィン共重合体(M−2)12.4gを得た。得られた重合体の分析結果を表2に示す。
末端不飽和エチレン・α−オレフィン共重合体(M−1)に換えて、末端不飽和エチレン・α−オレフィン共重合体(M−2)を3.0g用い工程(B)を実施したこと以外は実施例1と同様にオレフィン系樹脂を製造した。オレフィン系樹脂(α−3)を13.6g得た。オレフィン系樹脂(α−3)の分析結果を表3に示す。このオレフィン系樹脂(α−3)を潤滑油用粘度調整剤として評価した結果を表4に示す。
末端不飽和エチレン・α−オレフィン共重合体(M−2)の仕込み量を12.0gにして工程(B)を実施したこと以外は実施例3と同様にオレフィン系樹脂を製造した。オレフィン系樹脂(α−4)を23.4g得た。オレフィン系樹脂(α−4)の分析結果を表3に示す。このオレフィン系樹脂(α−4)を潤滑油用粘度調整剤として評価した結果を表4に示す。
オレフィン樹脂(α'−1)と末端不飽和エチレン・α−オレフィン共重合体(M−1)を42/58の重量比になるようにブレンドして潤滑油用粘度調整剤として評価した結果を表4に示す。すなわち比較例1では、実施例1における(α−1)の製造において用いた(M−1)と同等の割合で(M−1)を用いたが、実施例1とは異なりグラフト型オレフィン系重合体[R1]を含まない。
オレフィン樹脂(α'−1)と末端不飽和エチレン・α−オレフィン共重合体(M−1)を12/88の重量比になるようにブレンドして潤滑油用粘度調整剤として評価した。分析結果を表4に示す。すなわち比較例2では、実施例2における(α−2)の製造において用いた(M−1)と同等の割合で(M−1)を用いたが、実施例2とは異なりグラフト型オレフィン系重合体[R1]を含まない。
オレフィン樹脂(α'−1)と末端不飽和エチレン・α−オレフィン共重合体(M−2)を78/22の重量比になるようにブレンドして潤滑油用粘度調整剤として評価した。分析結果を表4に示す。すなわち比較例3では、実施例3における(α−3)の製造において用いた(M−2)と同等の割合で(M−2)を用いたが、実施例3とは異なりグラフト型オレフィン系重合体[R1]を含まない。
オレフィン樹脂(α'−1)と末端不飽和エチレン・α−オレフィン共重合体(M−2)を49/51の重量比になるようにブレンドして潤滑油用粘度調整剤として評価した。分析結果を表4に示す。すなわち比較例4では、実施例4における(α−4)の製造において用いた(M−2)と同等の割合で(M−2)を用いたが、実施例4とは異なりグラフト型オレフィン系重合体[R1]を含まない。
後述する比較例6で得たエチレン/プロピレン共重合体(EPR−1))と、後述する比較例8で得たエチレン/プロピレン共重合体(EPR−2)を30/70の重量比になるようにブレンドして潤滑油用粘度調整剤として評価した。分析結果を表4に示す。
エチレン/プロピレン共重合体(EPR−1)を次の方法で得た。
実施例1で説明したオレフィン系樹脂(α'-1)を用い潤滑油用粘度調整剤として評価した結果を表4に示す。
国際公開第2000/60032号に記載されている重合例6の方法を基に、水素仕込み量を90mLから200mLに、重合時間を5分間から4分間に変更しエチレン/プロピレン共重合体(EPR−2)を得た。得られたポリマーの分析結果を表3に、潤滑油用粘度調整剤として評価した結果を表4に示す。
水素仕込み量を200mLから150mLに変更した以外は、比較例8と同様の方法でエチレン/プロピレン共重合体(EPR−3)を得た。得られたポリマーの分析結果を表3に、潤滑油用粘度調整剤として評価した結果を表4に示す。
図1は、実施例および比較例における、鉱物油配合系潤滑油の相分離程度対CCS粘度(−30℃)をプロットした図である。実施例は比較例に比べて相分離程度が格段に優れていることがわかる。
Claims (16)
- 樹脂(α)を含む潤滑油用粘度調整剤であって、前記樹脂(α)が、下記要件(I)および(II)を満たし、かつ、主鎖および側鎖から構成され下記要件(i)および(ii)を満たすグラフト型オレフィン系重合体[R1]を含む、潤滑油用粘度調整剤。
(i)前記主鎖が、エチレンと、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンとの共重合体からなり、前記エチレンから導かれる構造単位が74〜86mol%の範囲にある。
(ii)前記側鎖が、エチレンと、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンとの共重合体からなり、前記エチレンから導かれる構造単位が30〜65mol%の範囲にある。
(I)示差走査熱量分析(DSC)によって測定された融点(Tm)が−20〜100℃の範囲にある。
(II)135℃のデカリン中で測定した極限粘度[η]が0.5〜2.5dl/gの範囲にある。 - 前記樹脂(α)が、下記要件(III)をさらに満たす、請求項1に記載の潤滑油用粘度調整剤。
(III)エチレンから導かれる構造単位の割合が全構造単位に対し40〜85mol%、炭素原子数3〜12のα−オレフィンから導かれる構造単位の割合が全構造単位に対し15〜60mol%(ただしエチレンから導かれる構造単位と、炭素原子数3〜12のα−オレフィンから導かれる構造単位との合計を100mol%とする)の範囲にある。 - 前記樹脂(α)が、エチレンから導かれる構造単位とプロピレンから導かれる構造単位とからなる、請求項1または2に記載の潤滑油用粘度調整剤。
- JIS K7112に準拠し密度勾配管法により測定した樹脂(α)の密度が850〜880kg/m3の範囲にある、請求項1〜3のいずれか一項に記載の潤滑油用粘度調整剤。
- 前記グラフト型オレフィン系重合体[R1]がさらに下記要件(iii)を満たす、請求項1〜4のいずれか一項に記載の潤滑油用粘度調整剤。
(iii)前記主鎖が、重量平均分子量が70000〜400000の範囲にあるエチレン・α−オレフィン共重合体に由来する。 - 前記グラフト型オレフィン系重合体[R1]がさらに下記要件(iv)を満たす、請求項1〜5のいずれか一項に記載の潤滑油用粘度調整剤。
(iv)前記側鎖が、重量平均分子量(Mw)が1000〜70000の範囲のエチレン・α−オレフィン共重合体に由来する。 - 下記(A)および(B)の工程を含む、請求項1〜6のいずれか一項に記載の潤滑油用粘度調整剤の製造方法。
(A)周期表第4族の遷移金属化合物[A]を含むオレフィン重合用触媒の存在下で、エチレンと、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンとを共重合し、末端不飽和エチレン・α−オレフィン共重合体を製造する工程。
(B)周期表第4族の遷移金属化合物[B]を含むオレフィン重合用触媒の存在下で、工程(A)で製造される末端不飽和エチレン・α−オレフィン共重合体と、エチレンと、炭素原子数3〜12のα−オレフィンから選ばれる少なくとも1種のα−オレフィンとを共重合し、樹脂(α)を製造する工程。 - 前記工程(A)で製造される末端不飽和エチレン・α−オレフィン共重合体が、エチレンから導かれる構造単位が30〜65mol%の範囲にあり、かつ、ゲルパーミエーションクロマトグラフィーで測定した重量平均分子量(Mw)が1000〜70000の範囲にある、請求項7に記載の潤滑油用粘度調整剤の製造方法。
- 前記周期表第4族の遷移金属化合物[A]が、ジメチルシリルビスインデニル骨格を有する配位子を含む周期表第4族の遷移金属化合物である、請求項7または8に記載の潤滑油用粘度調整剤の製造方法。
- 前記周期表第4族の遷移金属化合物[B]が、下記一般式[B]であらわされる架橋メタロセン化合物である、請求項7〜9のいずれか一項に記載の潤滑油用粘度調整剤の製造方法。
R6およびR11は水素原子、炭化水素基、ケイ素含有基およびケイ素含有基以外のヘテロ原子含有基から選ばれる同一の原子または同一の基であり、R7およびR10は水素原子、炭化水素基、ケイ素含有基およびケイ素含有基以外のヘテロ原子含有基から選ばれる同一の原子または同一の基であり、R6およびR7は互いに結合して環を形成していてもよく、R10およびR11は互いに結合して環を形成していてもよく;ただし、R6、R7、R10およびR11が全て水素原子であることはない。
R13およびR14はそれぞれ独立にアリール基を示す。
Y1は炭素原子またはケイ素原子を示す。
M1はジルコニウム原子またはハフニウム原子を示す。
Qはハロゲン原子、炭化水素基、ハロゲン化炭化水素基、炭素数4〜10の中性の共役もしくは非共役ジエン、アニオン配位子または孤立電子対で配位可能な中性配位子を示し、jは1〜4の整数を示し、jが2以上の整数の場合は複数あるQはそれぞれ同一でも異なっていてもよい。) - 前記工程(B)が重合温度90℃以上の溶液重合プロセスである、請求項7〜10のいずれか一項に記載の潤滑油用粘度調整剤の製造方法。
- 請求項1〜6のいずれか一項に記載の潤滑油用粘度調整剤1〜50質量部と、油(B)50〜99質量部と(ただし、潤滑油用粘度調整剤と、油(B)の合計を100質量部とする)を含む、潤滑油添加剤組成物。
- 請求項1〜6のいずれか一項に記載の潤滑油用粘度調整剤0.1〜5質量部と、潤滑油基材(BB)95〜99.9質量部と(ただし、潤滑油用粘度調整剤と、潤滑油基材(BB)の合計を100質量部とする)を含む、潤滑油組成物。
- さらに、流動点降下剤(C)を、該潤滑油組成物100質量%中に、0.05〜5質量%の量で含む、請求項13に記載の潤滑油組成物。
- 前記潤滑油基材(BB)が鉱物油である、請求項13または14に記載の潤滑油組成物。
- 前記潤滑油基材(BB)が合成油である、請求項13または14に記載の潤滑油組成物。
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WO2021200090A1 (ja) * | 2020-03-31 | 2021-10-07 | 三井化学株式会社 | オレフィン系樹脂およびその製造方法、ならびにプロピレン系樹脂組成物および該プロピレン系樹脂組成物を用いた成形体 |
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2016
- 2016-11-07 JP JP2017550297A patent/JP6545813B2/ja active Active
- 2016-11-07 EP EP16864143.9A patent/EP3375849A4/en not_active Withdrawn
- 2016-11-07 US US15/770,041 patent/US20180320102A1/en not_active Abandoned
- 2016-11-07 WO PCT/JP2016/082911 patent/WO2017082182A1/ja active Application Filing
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US20180320102A1 (en) | 2018-11-08 |
EP3375849A4 (en) | 2019-06-26 |
EP3375849A1 (en) | 2018-09-19 |
WO2017082182A1 (ja) | 2017-05-18 |
JPWO2017082182A1 (ja) | 2018-07-26 |
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