KR19990037293A - (메트)아크릴 단량체의 음이온성 중합을 통한 신규한 유동점 강하제 - Google Patents
(메트)아크릴 단량체의 음이온성 중합을 통한 신규한 유동점 강하제 Download PDFInfo
- Publication number
- KR19990037293A KR19990037293A KR1019980044291A KR19980044291A KR19990037293A KR 19990037293 A KR19990037293 A KR 19990037293A KR 1019980044291 A KR1019980044291 A KR 1019980044291A KR 19980044291 A KR19980044291 A KR 19980044291A KR 19990037293 A KR19990037293 A KR 19990037293A
- Authority
- KR
- South Korea
- Prior art keywords
- copolymer
- monomers
- lubricating oil
- group
- methacrylate
- Prior art date
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 37
- 238000010539 anionic addition polymerization reaction Methods 0.000 title claims abstract description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000003638 chemical reducing agent Substances 0.000 title 1
- 229920001577 copolymer Polymers 0.000 claims abstract description 53
- 239000003921 oil Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 10
- 230000001050 lubricating effect Effects 0.000 claims abstract description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 42
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 38
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 24
- 239000010687 lubricating oil Substances 0.000 claims description 18
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 239000012141 concentrate Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000314 lubricant Substances 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 230000000994 depressogenic effect Effects 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000003607 modifier Substances 0.000 claims description 3
- 239000003505 polymerization initiator Substances 0.000 claims description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 abstract description 7
- 125000000129 anionic group Chemical group 0.000 abstract description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract description 4
- 239000012429 reaction media Substances 0.000 abstract description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 8
- 239000002199 base oil Substances 0.000 description 7
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- -1 N, N-dimethylamino propyl methacryamide Chemical compound 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- QHHUCCOZVUZUSR-UHFFFAOYSA-N C=1C=CC=CC=1C([Na])C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C([Na])C1=CC=CC=C1 QHHUCCOZVUZUSR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WXXOGLNZLMRQEO-UHFFFAOYSA-N [Na]C(CCC([Na])(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1 Chemical compound [Na]C(CCC([Na])(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1 WXXOGLNZLMRQEO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-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
- 150000002148 esters Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- IRAPFUAOCHNONS-UHFFFAOYSA-N potassium;phenylmethylbenzene Chemical compound [K+].C=1C=CC=CC=1[CH-]C1=CC=CC=C1 IRAPFUAOCHNONS-UHFFFAOYSA-N 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- IXPWKHNDQICVPZ-UHFFFAOYSA-N 2-methylhex-1-en-3-yne Chemical compound CCC#CC(C)=C IXPWKHNDQICVPZ-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- 125000006539 C12 alkyl 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 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- RRAQGPNOVYEVCW-UHFFFAOYSA-N OC(=O)C=C.C1=CC(CCCCCCCCC)=CC=C1OC1=CC=C(CCCCCCCCC)C=C1 Chemical compound OC(=O)C=C.C1=CC(CCCCCCCCC)=CC=C1OC1=CC=C(CCCCCCCCC)C=C1 RRAQGPNOVYEVCW-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VEPKQEUBKLEPRA-UHFFFAOYSA-N VX-745 Chemical compound FC1=CC(F)=CC=C1SC1=NN2C=NC(=O)C(C=3C(=CC=CC=3Cl)Cl)=C2C=C1 VEPKQEUBKLEPRA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000011952 anionic catalyst Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- AASUFOVSZUIILF-UHFFFAOYSA-N diphenylmethanone;sodium Chemical compound [Na].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 AASUFOVSZUIILF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- MMVJBWFKSYKXIA-UHFFFAOYSA-N ethoxyethane;2-methylprop-2-enoic acid Chemical compound CCOCC.CC(=C)C(O)=O MMVJBWFKSYKXIA-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- URMHJZVLKKDTOJ-UHFFFAOYSA-N lithium;(3-methyl-1-phenylpentyl)benzene Chemical compound [Li+].C=1C=CC=CC=1[C-](CC(C)CC)C1=CC=CC=C1 URMHJZVLKKDTOJ-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- WDQKICIMIPUDBL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]prop-2-enamide Chemical compound CN(C)CCNC(=O)C=C WDQKICIMIPUDBL-UHFFFAOYSA-N 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LWZMBBGJTKGJCB-UHFFFAOYSA-N o-[2-(dimethylamino)ethyl] 2-methylprop-2-enethioate Chemical compound CN(C)CCOC(=S)C(C)=C LWZMBBGJTKGJCB-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YOTGRUGZMVCBLS-UHFFFAOYSA-N pentadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C(C)=C YOTGRUGZMVCBLS-UHFFFAOYSA-N 0.000 description 1
- GOZDOXXUTWHSKU-UHFFFAOYSA-N pentadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C=C GOZDOXXUTWHSKU-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- LCDOENXNMQXGFS-UHFFFAOYSA-N phenoxybenzene;prop-2-enoic acid Chemical compound OC(=O)C=C.C=1C=CC=CC=1OC1=CC=CC=C1 LCDOENXNMQXGFS-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005553 polystyrene-acrylate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 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
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 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 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
- C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
- C10M145/14—Acrylate; Methacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
실시예 번호 | 단량체(비율) | ~Mn(x 1000) | PP(℃)0.08 중량% | PP(℃)0.14 중량% | PP(℃)0.20 중량% | PP(℃)0.40 중량% |
1 | SMA : LMA(25 : 75) | 21 | -36 | -36 | ||
2 | SMA : LMA(45 : 55) | 33 | -33 | -33 | ||
3 | SMA : LMA(50 : 50) | 12.5 | -33 | -33 | -33 | |
4 | SMA : LMA(50 : 50) | 25 | -33 | -33 | -33 | |
5 | SMA : LMA(50 : 50) | 50 | -25 | -31 | ||
6 | SMA : LMA(50 : 50) | 75 | -27 | -33 | -33 | |
7 | SMA : LMA(75 : 25) | 25 | -21 | -21 | -24 | |
8 | SMA : BMA(50 : 50) | 25 | -30 | -30 | -30 | |
9 | SMA : BMA(50 : 50) | 50 | -28 | -33 | ||
10 | SMA : LMA : MMA(30 : 50 : 20) | 22 | -30 | -36 | ||
11 | SMA : LMA : MMA(30 : 50 : 20) | 35.5 | -27 | -33 | ||
12 | SMA : LMA : MMA(33 : 33 : 33) | 26 | -30 | -24 | ||
13 | SMA : LMA : BMA(33 : 33 : 33) | 25 | -36 | -36 | ||
14 | SMA : LMA : BMA(33 : 33 : 33) | 50 | -24 | -39 | ||
15 | SMA : LMA : BMA(33 : 33 : 33) | 75 | -33 | -36 | -33 | |
16 | SMA : LMA : BMA(35 : 13 : 52) | 25 | -33 | -33 | -33 | |
17 | SMA : LMA : BMA(35 : 13 : 52) | 50 | -30 | -33 |
실시예 번호 | 단량체(비율) | ~Mn(x 1000) | PP(℃)0.08 중량% | PP(℃)0.14 중량% | PP(℃)0.20 중량% | PP(℃)0.40 중량% |
18 | SMA : LMA : BMA(35 : 13 : 52) | 75 | -33 | -36 | -33 | |
19 | SMA : LMA : BMA(35 : 52 : 13) | 12.5 | -33 | -30 | -36 | |
20 | SMA : LMA : BMA(35 : 52 : 13) | 25 | -30 | -33 | -36 | |
21 | SMA : LMA : BMA(35 : 52 : 13) | 50 | -30 | -30 | -30 | |
22 | SMA : LMA : BMA(35 : 52 : 13) | 75 | -30 | -33 | -33 | |
23 | SMA : LMA : MMA(40 : 40 : 20) | 21.5 | -36 | -36 | ||
24 | SMA : LMA : MMA(40 : 40 : 20) | 93 | -30 | -33 | ||
25 | SMA : LMA : MMA(40 : 50 : 10) | -36 | -36 | |||
26 | SMA : LMA : BMA(40 : 40 : 20) | 26 | -36 | -39 | ||
27 | SMA : LMA : BMA(40 : 40 : 20) | 66.5 | -30 | -36 | ||
28 | SMA : LMA : MMA(50 : 40 : 10) | 24 | -33 | -36 | ||
29 | SMA : LMA : BMA(50 : 40 : 10) | 24.5 | -33 | -33 | ||
30 | SMA : LMA : MMA(60 : 30 : 10) | 10 | -33 | -33 | ||
31 | SMA : LMA : BMA(60 : 30 : 10) | 25 | -30 | -30 | ||
비교예 1 | 염기유 | -15 | ||||
비교예 2 | LMA : MMA(75 : 25) | 27.5 | -18 | -15 |
Claims (19)
- 하기로 이루어지는 혼합물의 음이온성 중합에 의해 제조된 공중합체 :a) 하기 화학식의 아크릴계 단량체 0 내지 60 중량 % :(상기 식에서, R 은 수소 또는 메틸, R1은 C1-5알킬기) ;b) 하기 화학식의 아크릴계 단량체 0 내지 60 중량 % :(상기 식에서, R 은 수소 또는 메틸, R2는 C6-14알킬기) ; 및c) 하기 화학식의 아크릴계 단량체 15 내지 80 중량 % :(상기 식에서, R 은 수소 또는 메틸, R3은 C15-22알킬기) ;[단, 하나 이상의 공단량체 a) 및 b)가 존재하고, 단량체 a) + b) 의 총량이 20 내지 85 중량 % 이다].
- 제 1 항에 있어서, 수평균 분자량이 약 500 내지 약 1,000,000 이고, 다분산도가 약 1.0 내지 약 2.0 인 공중합체.
- 제 1 항에 있어서, 다분산도가 약 1.0 내지 약 1.5 인 공중합체.
- 제 1 항에 있어서, 단량체 a)가 메틸 메트아크릴레이트, 부틸 메트아크릴레이트 및 이들의 혼합물로 구성된 군으로부터 선택된 공중합체.
- 제 1 항에 있어서, 단량체 b)가 라우릴 메트아크릴레이트인 공중합체.
- 제 1 항에 있어서, 단량체 c)가 스테아릴 메트아크릴레이트인 공중합체.
- 제 1 항에 있어서, 비-아크릴계 비닐 단량체 및 수행 향상 단량체로 이루어지는 군으로부터 선택된 하나 이상의 단량체를 추가로 포함하는 공중합체.
- 제 1 항에 있어서, 비활성 용매, 하기 식의 개시제 및 디페닐에틸렌으로 이루어진 중합 개시제 매질 중에서 음이온성 중합을 수행하는 공중합체 :R-M(상기 식에서, M 은 알칼리 금속 또는 알칼리 토금속이고, R 은 직쇄 또는 분지쇄 알킬 또는 시클로-알킬 또는 아릴이다)
- 제 8 항에 있어서, 단량체 전량를 중합 개시제 매질 중에 한번에 가하는 공중합체.
- 제 8 항에 있어서, 단량체를 연속법으로 중합 매질에 가하는 공중합체.
- 윤활유에 가하기 위한 농축물로서, 제 1 항의 공중합체 약 25 내지 약 75 중량 % 및 통상적인 액체 유기 희석제 약 75 내지 25 중량 % 로 이루어지는 농축물.
- 제 11 항에 있어서, 통상적인 액체 유기 희석제가 천연유, 합성유 및 이들의 혼합물로 구성되는 군으로부터 선택된 농축물.
- 제 11 항에 있어서, 점성도 향상제, 항산화제, 부식 저해제, 세정제, 분산제, 내구성 제제, 제포제, 해유화제 및 마찰 조절제로 구성되는 군으로부터 선택된 하나 이상의 첨가제를 추가로 포함하는 농축물.
- 제 1 항의 공중합체로 이루어지는 윤활유 제형에 사용되는 유동점 강하제.
- 제 1 항의 공중합체를 소량 포함하고 윤활 점성유로 주요 구성된 윤활유 제형.
- 제 15 항에 있어서, 공중합체가 처리될 윤활유의 질량 중 약 0.01 내지 1 중량 % 의 양으로 존재하는 윤활유.
- 제 15 항에 있어서, 윤활 점성유가 천연유, 합성유 및 이들의 혼합물로 이루어지는 군으로부터 선택된 윤활유.
- 제 15 항에 있어서, 점성도 향상제, 항산화제, 부식 저해제, 세정제, 분산제, 내구성제제, 제포제, 해유화제 및 마찰 조절제로 구성된 군으로부터 선택된 하나 이상의 첨가제를 추가로 포함하는 윤활제.
- 제 1 항의 공중합체의 소량을 윤활 점성유에 가하는 것으로 이루어지는 윤활유 조성물의 유동점의 향상 방법.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/957,046 US5834408A (en) | 1997-10-24 | 1997-10-24 | Pour point depressants via anionic polymerization of (meth)acrylic monomers |
US8/957,046 | 1997-10-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR19990037293A true KR19990037293A (ko) | 1999-05-25 |
Family
ID=25499003
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019980044291A KR19990037293A (ko) | 1997-10-24 | 1998-10-22 | (메트)아크릴 단량체의 음이온성 중합을 통한 신규한 유동점 강하제 |
Country Status (9)
Country | Link |
---|---|
US (1) | US5834408A (ko) |
EP (1) | EP0911348A3 (ko) |
JP (1) | JPH11302333A (ko) |
KR (1) | KR19990037293A (ko) |
CN (1) | CN1221002A (ko) |
AU (1) | AU8709198A (ko) |
BR (1) | BR9804058A (ko) |
CA (1) | CA2249244A1 (ko) |
SG (1) | SG68691A1 (ko) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6051538A (en) * | 1999-01-26 | 2000-04-18 | The Procter & Gamble Company | Pour point depression of heavy cut methyl esters via alkyl methacrylate copolymer |
DE69925239T2 (de) * | 1998-10-14 | 2006-01-19 | Jfe Steel Corp. | Beschichtungszusammensetzung und geschmierte metallbleche |
US6255261B1 (en) * | 1999-09-22 | 2001-07-03 | Ethyl Corporation | (Meth) acrylate copolymer pour point depressants |
DE10015533A1 (de) * | 1999-11-30 | 2001-06-28 | Rohmax Additives Gmbh | Blockcopolymere sowie Verfahren zur Hestellung und Verwendung |
US6323164B1 (en) * | 2000-11-01 | 2001-11-27 | Ethyl Corporation | Dispersant (meth) acrylate copolymers having excellent low temperature properties |
US20040092409A1 (en) * | 2002-11-11 | 2004-05-13 | Liesen Gregory Peter | Alkyl (meth) acrylate copolymers |
DE10314776A1 (de) * | 2003-03-31 | 2004-10-14 | Rohmax Additives Gmbh | Schmierölzusammensetzung mit guten Reibeigenschaften |
US7718588B2 (en) * | 2004-07-16 | 2010-05-18 | Kuraray Co., Ltd. | Lubricating oil additive containing acrylic polymer and lubricating oil compositions |
US8110211B2 (en) * | 2004-09-22 | 2012-02-07 | Advanced Cardiovascular Systems, Inc. | Medicated coatings for implantable medical devices including polyacrylates |
US20060252660A1 (en) * | 2005-05-09 | 2006-11-09 | Akhilesh Duggal | Hydrolytically stable viscosity index improves |
US8703167B2 (en) * | 2006-06-05 | 2014-04-22 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical devices for controlled release of a hydrophilic drug and a hydrophobic drug |
US20080008736A1 (en) * | 2006-07-06 | 2008-01-10 | Thierry Glauser | Random copolymers of methacrylates and acrylates |
JP5528693B2 (ja) * | 2008-12-17 | 2014-06-25 | コスモ石油ルブリカンツ株式会社 | エンジン油組成物 |
US8835367B2 (en) | 2009-06-04 | 2014-09-16 | The Lubrizol Corporation | Polymethacrylates as high VI viscosity modifiers |
CN101705120B (zh) * | 2009-11-20 | 2012-11-21 | 上海应用技术学院 | 柴油降凝剂助溶剂及其制备方法 |
BR112012012454A2 (pt) * | 2009-11-24 | 2017-10-10 | Lubrizol Corp | composição de lubrificação que contém combinação de modificador de viscosidade |
CN103459569B (zh) | 2011-03-25 | 2018-01-19 | 巴斯夫欧洲公司 | 具有改进的非牛顿粘度特性的润滑剂组合物 |
FR2982871A1 (fr) * | 2011-11-22 | 2013-05-24 | Univ Sud Toulon Var | Polymeres de poly(acrylate de n-alkyle)s et leur utilisation comme abaisseurs de point d'ecoulement de petrole |
CN102675527B (zh) * | 2012-05-18 | 2013-12-25 | 华南理工大学 | 一种水性长链丙烯酸酯类隔离剂的制备方法 |
FR3045660B1 (fr) * | 2015-12-21 | 2020-08-21 | Arkema France | Composition d'esters methyliques d'acides gras a bas point d'ecoulement |
JP2017186539A (ja) * | 2016-03-30 | 2017-10-12 | 三洋化成工業株式会社 | 潤滑油組成物 |
CN106590835B (zh) * | 2016-11-07 | 2019-07-05 | 泰州龙谷信息科技有限公司 | 一种甲醇发动机使用的润滑油降凝剂的制备方法 |
US20200123295A1 (en) * | 2017-06-30 | 2020-04-23 | Kuraray Co., Ltd. | Methacrylic copolymer and solution containing same |
JP6855342B2 (ja) * | 2017-07-11 | 2021-04-07 | Eneos株式会社 | 潤滑油組成物 |
WO2019173154A1 (en) * | 2018-03-05 | 2019-09-12 | Rohm And Haas Company | (meth)acrylate copolymer compositions and use thereof as pour point depressants for crude oil |
KR20210092765A (ko) * | 2018-11-13 | 2021-07-26 | 에보닉 오퍼레이션스 게엠베하 | 랜덤 공중합체의 제조 방법 |
MX2020002678A (es) | 2019-03-11 | 2020-09-25 | Evonik Operations Gmbh | Nuevos mejoradores del indice de viscosidad. |
ES2950909T3 (es) | 2020-05-05 | 2023-10-16 | Evonik Operations Gmbh | Copolímeros de polidieno lineales hidrogenados como material base o aditivos lubricantes para composiciones lubricantes |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3304260A (en) * | 1960-12-30 | 1967-02-14 | Monsanto Co | Compositions of improved viscosity index containing alkyl polymethacrylate of high relative syndiotacticity |
US3252949A (en) * | 1960-12-30 | 1966-05-24 | Monsanto Co | Syndiotactic oil-soluble methacrylate polymers |
FR2131111A5 (en) * | 1971-03-31 | 1972-11-10 | Inst Francais Du Petrole | Heat stable polymethacrylates - prepd in olefin soln and useful in lubricants |
US4146492A (en) * | 1976-04-02 | 1979-03-27 | Texaco Inc. | Lubricant compositions which exhibit low degree of haze and methods of preparing same |
ES8605832A1 (es) * | 1984-01-30 | 1986-04-01 | Empresa Nac Petroleo | Procedimiento de obtencion de aditivos polifuncionales de aceites lubricantes |
US4606834A (en) * | 1985-09-10 | 1986-08-19 | Texaco Inc. | Lubricating oil containing VII pour depressant |
FR2589866B1 (fr) * | 1985-11-07 | 1988-07-15 | Inst Francais Du Petrole | Compositions de copolymeres, utilisables comme additifs pour huiles lubrifiantes |
DE3607444A1 (de) * | 1986-03-07 | 1987-09-10 | Roehm Gmbh | Additive fuer mineraloele mit stockpunktverbessernder wirkung |
US5112509A (en) * | 1988-12-22 | 1992-05-12 | Texaco, Inc. | Non-dispersant, shear-stabilizing, and wear-inhibiting viscosity index improver |
DE3930142A1 (de) * | 1989-09-09 | 1991-03-21 | Roehm Gmbh | Dispergierwirksame viskositaets-index-verbesserer |
US5272211A (en) * | 1992-12-21 | 1993-12-21 | Shell Oil Company | Block copolymers of dienes, vinylarenes, and alkylmethacrylates as modified viscosity index improvers |
US5534175A (en) * | 1992-12-28 | 1996-07-09 | The Lubrizol Corporation | Copolymers of unsaturated fatty esters, their use as viscosity improver and lubricating oil containing said copolymers |
US5312884A (en) * | 1993-04-30 | 1994-05-17 | Rohm And Haas Company | Copolymer useful as a pour point depressant for a lubricating oil |
IT1270673B (it) * | 1994-10-19 | 1997-05-07 | Euron Spa | Additivo multifunzionale per olii lubrificanti compatibili con fluoroelastomeri |
US5552491A (en) * | 1995-01-27 | 1996-09-03 | Ethyl Additives Corporation | Star-branched acrylate and methacrylate polymers |
AU4913796A (en) * | 1995-01-27 | 1996-08-14 | Texaco Development Corporation | Process for the anionic polymerization of acrylic monomers |
-
1997
- 1997-10-24 US US08/957,046 patent/US5834408A/en not_active Expired - Fee Related
-
1998
- 1998-09-29 AU AU87091/98A patent/AU8709198A/en not_active Abandoned
- 1998-09-30 CA CA002249244A patent/CA2249244A1/en not_active Abandoned
- 1998-10-01 SG SG1998003962A patent/SG68691A1/en unknown
- 1998-10-08 EP EP98308203A patent/EP0911348A3/en not_active Withdrawn
- 1998-10-20 JP JP10315372A patent/JPH11302333A/ja active Pending
- 1998-10-22 KR KR1019980044291A patent/KR19990037293A/ko not_active Application Discontinuation
- 1998-10-22 BR BR9804058-8A patent/BR9804058A/pt unknown
- 1998-10-23 CN CN98123436A patent/CN1221002A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
CN1221002A (zh) | 1999-06-30 |
CA2249244A1 (en) | 1999-04-24 |
AU8709198A (en) | 1999-05-13 |
SG68691A1 (en) | 1999-11-16 |
EP0911348A2 (en) | 1999-04-28 |
US5834408A (en) | 1998-11-10 |
BR9804058A (pt) | 1999-12-14 |
EP0911348A3 (en) | 2000-04-12 |
JPH11302333A (ja) | 1999-11-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5834408A (en) | Pour point depressants via anionic polymerization of (meth)acrylic monomers | |
EP0936225B1 (en) | Process for the preparation of acrylate and methacrylate polymers | |
US5552491A (en) | Star-branched acrylate and methacrylate polymers | |
CA2276900C (en) | (meth)acrylate copolymers having excellent low temperature properties | |
JP2509199B2 (ja) | 改良された粘度指数を有する高剪断安定汎用潤滑油 | |
CA2396671C (en) | Copolymers that can be obtained using atrp methods, as well as methods for their production and use | |
CA2396681C (en) | Gradient copolymers as well as methods for their production and use | |
RU2483083C2 (ru) | Применение гребенчатых полимеров для снижения расхода горючего | |
US5070131A (en) | Gear oil viscosity index improvers | |
US3816314A (en) | Block copolymers of unsaturated ester and a nitrogen containing monomer as v.i.improving and dispersant additives for oils | |
CN103254974A (zh) | 具有优良摩擦性能的润滑油组合物 | |
KR20150143721A (ko) | 연료 소비를 감소시키기 위한 변속기 오일 제제 | |
EP2406359A1 (de) | Verwendung von kammpolymeren zur verbesserung des lasttragevermögens | |
US5043087A (en) | Addives for paraffinic lubricants | |
CA2392727C (en) | Block copolymers and a method for their preparation and use | |
JPH0830099B2 (ja) | 潤滑油用添加剤として使用しうる共重合体組成物 | |
US5484866A (en) | Concentrates of a highly branched polymer and functional fluids prepared therefrom | |
JPH07292379A (ja) | 粘度指数向上剤及び潤滑油 | |
JPH07268372A (ja) | 粘度指数向上剤及び潤滑油 | |
JPH04100896A (ja) | 粘度指数向上剤 | |
JPH07268373A (ja) | 粘度指数向上剤および潤滑油 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19981022 |
|
A201 | Request for examination | ||
PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19981224 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19981022 Comment text: Patent Application |
|
PG1501 | Laying open of application | ||
E902 | Notification of reason for refusal | ||
PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20000826 Patent event code: PE09021S01D |
|
E601 | Decision to refuse application | ||
PE0601 | Decision on rejection of patent |
Patent event date: 20010409 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20000826 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |