EP2899255B1 - Oil composition comprising a viscosity index improver - Google Patents

Oil composition comprising a viscosity index improver Download PDF

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Publication number
EP2899255B1
EP2899255B1 EP14763262.4A EP14763262A EP2899255B1 EP 2899255 B1 EP2899255 B1 EP 2899255B1 EP 14763262 A EP14763262 A EP 14763262A EP 2899255 B1 EP2899255 B1 EP 2899255B1
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EP
European Patent Office
Prior art keywords
derived
constitutional unit
mass
oil composition
conjugated diene
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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Application number
EP14763262.4A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP2899255A1 (en
EP2899255A4 (en
Inventor
Yosuke Uehara
Hiromitsu Sasaki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kuraray Co Ltd
Amyris Inc
Original Assignee
Kuraray Co Ltd
Amyris Inc
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Publication date
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Publication of EP2899255A1 publication Critical patent/EP2899255A1/en
Publication of EP2899255A4 publication Critical patent/EP2899255A4/en
Application granted granted Critical
Publication of EP2899255B1 publication Critical patent/EP2899255B1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/12—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing conjugated diene
    • 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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/68—Shear stability
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present invention relates to an oil composition
  • an oil composition comprising a base oil and a viscosity index improver, the viscosity index improver consisting of a hydrogenated product of a block copolymer containing a constitutional unit derived from farnesene, and a process for producing the oil composition.
  • the present invention aims at providing an oil composition, comprising a base oil and a viscosity index improver, the oil composition being enhanced in viscosity index and high-temperature high-shear viscosity, and the viscosity index improver being excellent in an effect of improving a viscosity index and a high-temperature high-shear viscosity of oils, and a process for producing the oil composition.
  • the viscosity index improver is constituted of a hydrogenated product of a block copolymer including a polymer block (A) containing the constitutional unit (a) derived from the aromatic vinyl compound as a main component and a polymer block (B) containing the constitutional unit (b) derived from the conjugated diene as a main component (hereinafter also referred to merely as a "hydrogenated block copolymer").
  • Examples of compounds as a component from which the other constitutional unit (c) is derived include unsaturated hydrocarbon compounds such as propylene, 1-butene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-octene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene and 1-eicosene; functional group-containing unsaturated compounds such as acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, acrylonitrile, methacrylonitrile, maleic acid, fumaric acid, crotonic acid, itaconic acid, 2-acryloylethanesulfonic acid, 2-methacryloylethanesulfonic acid, 2-acrylamide-2-methylpropanes
  • the content of the constitutional unit (c) in a whole amount of the constitutional units constituting the copolymer is preferably not more than 40% by mass, more preferably not more than 20% by mass, still more preferably not more than 10% by mass, and even still more preferably not more than 1% by mass.
  • the copolymer is in the form of a block copolymer including a polymer block (A) containing the constitutional unit (a) derived from the aromatic vinyl compound as a main component and a polymer block (B) containing the constitutional unit (b) derived from the conjugated diene as a main component.
  • copolymerizable monomers may be used alone or in combination of any two or more thereof.
  • the constitutional unit may be bonded thereto either in a random form or in a tapered form.
  • the obtained hydrogenated block copolymer can be prevented from forming a gel-like network in an oil composition, and the oil composition obtained therefrom can be prevented from suffering from increase in kinetic viscosity thereof as measured at a temperature of each of 40°C and 100°C. As a result, the use of the oil composition as a lubricating oil is facilitated.
  • the hydrogenated copolymer constituting the viscosity index improver is produced by hydrogenating the aforementioned copolymer in which 50 mol% or more of carbon-carbon double bonds in the constitutional unit (b) derived from the conjugated diene are hydrogenated, namely the hydrogenated copolymer has a hydrogenation rate of 50 mol% or more.
  • the peak top molecular weight (Mp) as used in the present specification means the value measured by the method described below in Examples.
  • the hydrogenated block copolymer may be suitably produced by a process including a polymerization step of obtaining a block copolymer including a polymer block (A) containing the constitutional unit (a) derived from the aromatic vinyl compound as a main component and a polymer block (B) containing the constitutional unit (b) derived from the conjugated diene as a main component by anionic polymerization; and a hydrogenation step of hydrogenating 50 mol% or more of carbon-carbon double bonds in the constitutional unit (b) derived from the conjugated diene.
  • anionic polymerization initiator examples include alkali metals such as lithium, sodium and potassium; alkali earth metals such as beryllium, magnesium, calcium, strontium and barium; lanthanoid-based rare earth metals such as lanthanum and neodymium; and compounds containing the above alkali metals, alkali earth metals or lanthanoid-based rare earth metals.
  • alkali metals such as lithium, sodium and potassium
  • alkali earth metals such as beryllium, magnesium, calcium, strontium and barium
  • lanthanoid-based rare earth metals such as lanthanum and neodymium
  • compounds containing the above alkali metals, alkali earth metals or lanthanoid-based rare earth metals are preferred.
  • organic alkali metal compounds include organic lithium compounds such as methyl lithium, ethyl lithium, n-butyl lithium, sec-butyl lithium, t-butyl lithium, hexyl lithium, phenyl lithium, stilbene lithium, dilithiomethane, dilithionaphthalene, 1,4-dilithiobutane, 1,4-dilithio-2-ethyl cyclohexane and 1,3,5-trilithiobenzene; and sodium naphthalene and potassium naphthalene, etc.
  • organic lithium compounds such as methyl lithium, ethyl lithium, n-butyl lithium, sec-butyl lithium, t-butyl lithium, hexyl lithium, phenyl lithium, stilbene lithium, dilithiomethane, dilithionaphthalene, 1,4-dilithiobutane, 1,4-dilithio-2-ethyl cyclohexane and 1,3,
  • organic alkali metal compounds preferred are organic lithium compounds; more preferred are n-butyl lithium and sec-butyl lithium; and still more preferred is sec-butyl lithium.
  • the organic alkali metal compound may be reacted with a secondary amine such as diisopropylamine, dibutylamine, dihexylamine and dibenzylamine to use the compound in the form of an organic alkali metal amide.
  • the amount of the organic alkali metal compound used for the polymerization may vary depending upon a molecular weight of the resulting block copolymer, and is usually in the range of from 0.01 to 3% by mass on the basis of a total amount of the aromatic vinyl compound, and farnesene and/or the conjugated diene other than farnesene.
  • the block copolymer obtained by the above method is subjected to hydrogenation step, it is possible to produce the hydrogenated block copolymer.
  • the hydrogenation method there may be used conventionally known methods. For example, a solution prepared by dissolving the block copolymer in a solvent that has no adverse influence on the hydrogenation reaction is subjected to hydrogenation reaction in the presence of a hydrogenation catalyst.
  • the hydrogenation catalyst examples include Ziegler-based catalysts; metal-supported catalysts obtained by supporting a metal such as nickel, platinum, palladium, ruthenium and rhodium on a carrier such as carbon, silica and diatomaceous earth; and organic metal complexes containing a metal such as cobalt, nickel, palladium, rhodium and ruthenium.
  • the hydrogenation reaction may be carried out by adding the hydrogenation catalyst to the polymerization reaction solution containing the block copolymer obtained by the above method for producing the block copolymer.
  • a hydrogen pressure used therein is preferably from 0.1 to 20 MPa
  • the reaction temperature is preferably from 100 to 200°C
  • the reaction time is preferably from 1 to 20 h.
  • the hydrogenation rate of carbon-carbon double bonds in the polymer block (B) contained in the block copolymer is preferably not less than 50 mol%, more preferably not less than 60 mol%, and still more preferably not less than 70 mol%, from the viewpoint of improving a heat resistance and a shear stability of oils as well as a viscosity index and a high-temperature high-shear viscosity of oils. Meanwhile, the hydrogenation rate may be calculated by the method described below in Examples.
  • the oil composition of the present invention includes a base oil and the aforementioned viscosity index improver.
  • the oil composition may be suitably used as an engine oil, an automatic transmission oil, a gear lube oil and a hydraulic pressure oil.
  • the content of the viscosity index improver in the oil composition is from 0.1 to 10% by mass, preferably from 0.1 to 7% by mass, still more preferably from 0.2 to 5% by mass, and even still more preferably from 0.5 to 5% by mass.
  • the base oil examples include fuel oils such as intermediate fraction fuels, synthetic or natural lubricating oils, unrefined oils and industrial oils.
  • the base oil may be at least one compound selected from the group consisting of a paraffin-based compound, a naphthene-based compound and an aromatic compound.
  • the base oil may also be at least one oil selected from the group consisting of a natural oil and an artificially synthesized oil.
  • the oil composition of the present invention may be produced by methods conventionally known in the art.
  • the oil composition of the present invention may be produced by mixing the aforementioned base oil with the aforementioned viscosity index improver.
  • the mixing of these components may be carried out using conventionally known mixers.
  • ⁇ -farnesene purity: 97.6% by mass; available from Amyris Biotechnologies Inc.
  • ⁇ -farnesene purified using a 3 ⁇ molecular sieve and distilled under a nitrogen atmosphere to remove hydrocarbon-based impurities such as zingiberene, bisabolene, farnesene epoxide, farnesol isomers, E,E-farnesol, squalene, ergosterol and several kinds of dimers of farnesene therefrom, and the thus purified ⁇ -farnesene was used in the following polymerization.
  • Hydrogenation Rate ⁇ 1 - (number of moles of carbon-carbon double bonds contained per 1 mole of hydrogenated block copolymer)/(number of moles of carbon-carbon double bonds contained per 1 mole of block copolymer ⁇ x 100 (mol%)
  • reaction solution Added into the reaction solution was palladium carbon (amount of palladium supported: 5% by mass) as a hydrogenation catalyst which was used in an amount of 5% by mass on the basis of the block copolymer, and the block copolymer was subjected to hydrogenation reaction under a hydrogen pressure of 2 MPa at a temperature of 150°C for 10 h.
  • the obtained reaction mixture was allowed to stand for cooling and pressure releasing, and then subjected to filtration to remove the palladium carbon therefrom.
  • Example 2 The same procedure as in Example 1 was repeated except that the respective components were formulated as shown in Table 1, thereby obtaining a hydrogenated block copolymer (A4) and an oil composition and subjecting the resulting products to the above evaluation. The results are shown in Tables 1 and 2.
  • Example 2 The subsequent procedure was conducted in the same manner as in Example 1 except that the resulting hydrogenated block copolymer (A5) and the base oil were formulated as shown in Table 2, thereby obtaining an oil composition.
  • the thus obtained oil composition was subjected to the above evaluation. The results are shown in Table 2.
  • F-St Poly( ⁇ -farnesene)-polystyrene diblock copolymer.
  • F/Bd-St Poly( ⁇ -farnesene/butadiene)-polystyrene diblock copolymer.
  • F/IP-St Poly( ⁇ -farnesene/isoprene)-polystyrene diblock copolymer.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Lubricants (AREA)
  • Graft Or Block Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP14763262.4A 2013-03-11 2014-03-06 Oil composition comprising a viscosity index improver Active EP2899255B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013048290 2013-03-11
PCT/JP2014/055800 WO2014142001A1 (ja) 2013-03-11 2014-03-06 粘度指数向上剤、その製造方法及び油組成物

Publications (3)

Publication Number Publication Date
EP2899255A1 EP2899255A1 (en) 2015-07-29
EP2899255A4 EP2899255A4 (en) 2015-10-28
EP2899255B1 true EP2899255B1 (en) 2017-08-02

Family

ID=51536664

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14763262.4A Active EP2899255B1 (en) 2013-03-11 2014-03-06 Oil composition comprising a viscosity index improver

Country Status (8)

Country Link
US (1) US20150284656A1 (ja)
EP (1) EP2899255B1 (ja)
JP (1) JP5671658B1 (ja)
KR (1) KR101552090B1 (ja)
CN (1) CN104704090A (ja)
CA (1) CA2888668C (ja)
TW (1) TWI526527B (ja)
WO (1) WO2014142001A1 (ja)

Families Citing this family (10)

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Publication number Priority date Publication date Assignee Title
ES2620090T3 (es) * 2013-09-30 2017-06-27 Kuraray Co., Ltd. Composición de elastómero termoplástico y cuerpo moldeado
CA2910452C (en) * 2013-09-30 2016-04-05 Kuraray Co., Ltd. Polyolefin-based resin composition and molded body
US9994669B2 (en) * 2016-01-06 2018-06-12 Fina Technology, Inc. Polyols derived from farnesene for polyurethanes
US10544241B2 (en) * 2016-09-15 2020-01-28 Fina Technology, Inc. Farnesene-based macromonomers and methods of making and using the same
US10370523B2 (en) 2017-04-03 2019-08-06 Fina Technology, Inc. Insulating glass sealants based on polyurethanes and organically-modified nanoclays
JP7141027B2 (ja) * 2018-07-05 2022-09-22 株式会社クラレ 成形体
CN109504495B (zh) * 2019-01-25 2022-02-01 中沃能源(湖北)集团有限公司 一种润滑油用改进剂及其制备工艺
US11466118B2 (en) 2019-11-22 2022-10-11 Fina Technology, Inc. Chain end hydroxyl functionalized branched polyfarnesenes obtained by radical polymerization
WO2021215255A1 (ja) * 2020-04-20 2021-10-28 株式会社クラレ 熱可塑性エラストマー組成物、積層構造体及び該積層構造体の製造方法
WO2024047952A1 (ja) * 2022-08-31 2024-03-07 三菱ケミカル株式会社 重合体、摩擦調整剤、潤滑油添加剤及びその製造方法、並びに潤滑油

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Also Published As

Publication number Publication date
CN104704090A (zh) 2015-06-10
US20150284656A1 (en) 2015-10-08
CA2888668C (en) 2016-10-18
EP2899255A1 (en) 2015-07-29
KR101552090B1 (ko) 2015-09-09
JP5671658B1 (ja) 2015-02-18
JPWO2014142001A1 (ja) 2017-02-16
KR20150048902A (ko) 2015-05-07
TW201443209A (zh) 2014-11-16
WO2014142001A1 (ja) 2014-09-18
CA2888668A1 (en) 2014-09-18
EP2899255A4 (en) 2015-10-28
TWI526527B (zh) 2016-03-21

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