JP6682302B2 - Viscosity index improver and lubricating oil composition - Google Patents
Viscosity index improver and lubricating oil composition Download PDFInfo
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- JP6682302B2 JP6682302B2 JP2016045112A JP2016045112A JP6682302B2 JP 6682302 B2 JP6682302 B2 JP 6682302B2 JP 2016045112 A JP2016045112 A JP 2016045112A JP 2016045112 A JP2016045112 A JP 2016045112A JP 6682302 B2 JP6682302 B2 JP 6682302B2
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- 239000010687 lubricating oil Substances 0.000 title claims description 55
- 239000000203 mixture Substances 0.000 title claims description 55
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- 229920000642 polymer Polymers 0.000 claims description 103
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000003999 initiator Substances 0.000 claims description 19
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000962 organic group Chemical group 0.000 claims description 7
- 239000000470 constituent Substances 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- -1 2-ethylhexyl Chemical group 0.000 description 66
- 239000000178 monomer Substances 0.000 description 46
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- 238000006116 polymerization reaction Methods 0.000 description 35
- 238000000034 method Methods 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
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- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- QMJUKLOOIAWREN-UHFFFAOYSA-N prop-2-enyl 2-(2-prop-2-enoxycarbonylphenyl)benzoate Chemical compound C=CCOC(=O)C1=CC=CC=C1C1=CC=CC=C1C(=O)OCC=C QMJUKLOOIAWREN-UHFFFAOYSA-N 0.000 description 1
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- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
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- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- ZPXYTWHLXRHOPX-UHFFFAOYSA-N sulfanyloxymethanethioic s-acid Chemical class SOC(S)=O ZPXYTWHLXRHOPX-UHFFFAOYSA-N 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical class SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
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- 230000001629 suppression Effects 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- XTXFUQOLBKQKJU-UHFFFAOYSA-N tert-butylperoxy(trimethyl)silane Chemical compound CC(C)(C)OO[Si](C)(C)C XTXFUQOLBKQKJU-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical class [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は、特定の構造を有する粘度指数向上剤及びその製造方法、並びにこれを含有する潤滑油組成物に関する。特に、高い粘度指数と良好なせん断安定性を有し、かつ、潤滑油に対して十分な溶解性を示す粘度指数向上剤に関する。 The present invention relates to a viscosity index improver having a specific structure, a method for producing the same, and a lubricating oil composition containing the same. In particular, the present invention relates to a viscosity index improver having a high viscosity index, good shear stability, and sufficient solubility in lubricating oil.
近年、内燃機関用潤滑油は省燃費特性の向上が強く求められており、1つの手段として潤滑油の低粘度化による粘性抵抗の低減が挙げられている。しかし、単なる低粘度化では液漏れや焼きつきという問題が生じるため、高温での粘度を高く保持しながら低温での粘度を低く保つ効果を有する粘度指数向上剤の添加が有効である。 In recent years, lubricating oils for internal combustion engines have been strongly demanded to have improved fuel economy characteristics, and as one means, reduction of viscous resistance by lowering the viscosity of lubricating oils is mentioned. However, since simply lowering the viscosity causes problems such as liquid leakage and seizure, it is effective to add a viscosity index improver having an effect of keeping the viscosity at high temperature low while keeping the viscosity at high temperature low.
粘度指数向上剤には重合体を含有するものが知られており、さまざまな種類がある。なかでも、アルキル(メタ)アクリレート重合体からなる粘度指数向上剤は、高い粘度指数向上効果を示す。一方で、アルキル(メタ)アクリレート重合体からなる粘度指数向上剤は、せん断安定性が悪いため、長期使用時に省燃費特性が低下する(ロングライフ性が悪い)という問題があった。 It is known that the viscosity index improver contains a polymer, and there are various types. Among them, the viscosity index improver composed of an alkyl (meth) acrylate polymer exhibits a high effect of improving the viscosity index. On the other hand, the viscosity index improver made of an alkyl (meth) acrylate polymer has poor shear stability, and therefore has a problem that fuel saving characteristics are deteriorated during long-term use (long life is poor).
せん断安定性を改善する手段としては、例えば、粘度指数向上剤に含まれる重合体の分子量を小さくすることが挙げられる。一般に、低分子量ほどせん断の影響を受けにくく分子量低下幅が小さくなるため、低分子量の粘度指数向上剤を用いることで、せん断後の粘度低下を抑制することが可能である(特許文献1および非特許文献1)。また、コア部にジビニルベンゼンを用いた星型構造を有する重合体により、せん断安定性の向上を試みた報告もなされている(特許文献2)。 Examples of means for improving the shear stability include reducing the molecular weight of the polymer contained in the viscosity index improver. Generally, the lower the molecular weight, the less susceptible to shearing and the smaller the molecular weight decrease range. Therefore, by using a low molecular weight viscosity index improver, it is possible to suppress the viscosity decrease after shearing (Patent Document 1 and Non-Patent Document 1). Patent Document 1). In addition, it has been reported that a polymer having a star-shaped structure using divinylbenzene in the core portion attempts to improve shear stability (Patent Document 2).
しかしながら、一般に低分子量であるほど粘度指数向上効果は低い傾向があるため、低分子量の粘度指数向上剤を用いた場合は、粘度指数は低くなるという課題が発生する。さらに、所望の粘度に調整するためには、粘度指数向上剤の使用量を増やす必要があり、コスト面で不利となりやすい。また、コア部にジビニルベンゼンを用いた星型構造を有する重合体を用いた場合でも、粘度指数とせん断安定性の両立には依然改善の余地があり、良好なせん断安定性を維持しながら高い粘度指数を示す粘度指数向上剤が望まれていた。 However, in general, the lower the molecular weight, the lower the effect of improving the viscosity index. Therefore, when a low molecular weight viscosity index improver is used, the viscosity index becomes low. Furthermore, in order to adjust the viscosity to a desired value, it is necessary to increase the amount of the viscosity index improver used, which tends to be disadvantageous in terms of cost. Further, even when a polymer having a star structure using divinylbenzene is used in the core part, there is still room for improvement in achieving both a viscosity index and shear stability, and it is high while maintaining good shear stability. A viscosity index improver showing a viscosity index has been desired.
本発明は上記の問題点に鑑みてなされたものであり、その目的は、良好なせん断安定性を維持しながら高い粘度指数を示す重合体を含有する粘度指数向上剤、並びに該粘度指数向上剤を用いた潤滑油組成物を提供することである。 The present invention has been made in view of the above problems, and an object thereof is a viscosity index improver containing a polymer showing a high viscosity index while maintaining good shear stability, and the viscosity index improver. Is to provide a lubricating oil composition.
本願発明者らは、鋭意検討を重ねたところ、以下の方法によって、上記目的を達成する粘度指数向上剤を見出した。 The inventors of the present invention have conducted extensive studies and have found a viscosity index improver that achieves the above object by the following method.
すなわち本発明は、一般式(1)で示される単位(以下、「(a)単位」と称する)を必須構成単位とする重合体を含有し、該重合体の重量平均分子量(Mw)が20000以上500000未満である粘度指数向上剤である。 That is, the present invention contains a polymer having a unit represented by the general formula (1) (hereinafter, referred to as “(a) unit”) as an essential constituent unit, and the weight average molecular weight (Mw) of the polymer is 20,000. It is a viscosity index improver having a viscosity of at least 500000.
(式中、R1及びR2はそれぞれ独立に、水素原子またはアルキル基であり、Xは炭素数が8〜40の有機基である。)
該重合体は、前記(a)単位に加え、炭素数が6〜40の脂肪族炭化水素基を有するアルキル(メタ)アクリレート由来の単位(以下、「(b)単位」と称する)と炭素数が1〜5の脂肪族炭化水素基を有するアルキル(メタ)アクリレート由来の単位(以下、「(c)単位」と称する)を有することが好ましい。
(In the formula, R 1 and R 2 are each independently a hydrogen atom or an alkyl group, and X is an organic group having 8 to 40 carbon atoms.)
The polymer has, in addition to the (a) unit, a unit derived from an alkyl (meth) acrylate having an aliphatic hydrocarbon group having 6 to 40 carbon atoms (hereinafter referred to as "(b) unit") and carbon number. Preferably has a unit derived from an alkyl (meth) acrylate having 1 to 5 aliphatic hydrocarbon groups (hereinafter referred to as "(c) unit").
該重合体100質量部に対し、(a)単位の量が、5質量部以上65質量部以下であることが好ましい。 The amount of the unit (a) is preferably 5 parts by mass or more and 65 parts by mass or less based on 100 parts by mass of the polymer.
該重合体100質量部に対し、(a)単位の量および(c)単位の量の合計が、30質量部以上95質量部未満であることが好ましい。 The total amount of the units (a) and (c) is preferably 30 parts by mass or more and less than 95 parts by mass with respect to 100 parts by mass of the polymer.
本発明は、上記粘度指数向上剤を含有する潤滑油組成物も提供する。 The present invention also provides a lubricating oil composition containing the above viscosity index improver.
本発明の粘度指数向上剤を用いることで、従来の潤滑油組成物と比べせん断安定性および耐熱性が改良できる。また、本発明の粘度指数向上剤は、高分子量でありながら基油への十分な溶解性を確保することが容易になるため、粘度指数が高い潤滑油組成物を提供することができる。 By using the viscosity index improver of the present invention, shear stability and heat resistance can be improved as compared with conventional lubricating oil compositions. Further, the viscosity index improver of the present invention can easily secure sufficient solubility in a base oil even though it has a high molecular weight, so that a lubricating oil composition having a high viscosity index can be provided.
以下に本発明を詳述する。これ以降の説明において特に記載がない限り、「部」は「質量部」、「%」は「質量%」をそれぞれ意味する。また、範囲を示す「A〜B」は、A以上B以下であることを示す。 The present invention is described in detail below. In the following description, "part" means "part by mass" and "%" means "% by mass" unless otherwise specified. Further, “A to B” indicating the range indicates that it is A or more and B or less.
〔1.粘度指数向上剤〕
本発明の粘度指数向上剤に含まれる重合体は、一般式(1)で示される(a)単位を必須構成単位とする重合体を含有し、該重合体の重量平均分子量(Mw)が20000以上500000未満である粘度指数向上剤である。
[1. Viscosity index improver)
The polymer contained in the viscosity index improver of the present invention contains a polymer having the unit (a) represented by the general formula (1) as an essential constituent unit, and the weight average molecular weight (Mw) of the polymer is 20,000. It is a viscosity index improver having a viscosity of at least 500000.
(式中、R1及びR2はそれぞれ独立に、水素原子またはアルキル基であり、Xは炭素数が8〜40の有機基である。)
(a)単位を必須構成単位とするためには、マレイミド系単量体を重合することが好ましい。一般式(1)のXは、炭素数が8〜40の有機基であれば特に制限はなく、任意の置換基が結合していてもよい。ただし、前記有機基における炭素原子および水素原子以外の原子数は基油溶解性確保の観点から0以上10以下が好ましい。前記有機基のとしては、例えば、直鎖状または分岐鎖状、環状のアルキル基、アリール基、H(CH2)6−O−(CH2)2−O−(CH2)4−のようなオキサアルキル基が挙げられる。
(In the formula, R 1 and R 2 are each independently a hydrogen atom or an alkyl group, and X is an organic group having 8 to 40 carbon atoms.)
In order to make the unit (a) an essential constituent unit, it is preferable to polymerize a maleimide-based monomer. X in the general formula (1) is not particularly limited as long as it is an organic group having 8 to 40 carbon atoms, and any substituent may be bonded. However, the number of atoms other than carbon atoms and hydrogen atoms in the organic group is preferably 0 or more and 10 or less from the viewpoint of ensuring solubility of the base oil. As the said organic group is, for example, linear or branched, cyclic alkyl group, an aryl group, H (CH 2) 6 -O- (CH 2) 2 -O- (CH 2) 4 - like Oxaalkyl group.
マレイミド系単量体の具体例としては、例えば、N−オクチルマレイミド、N−2−エチルヘキシルマレイミド、N−デシルマレイミド、N−ラウリルマレイミド、N−テトラデシルマレイミド、N−ステアリルマレイミド、N−2−デシルテトラデシルマレイミド等が挙げられる。これらの中でも入手性や経済性の観点および基油への溶解性が高いことから、N−ラウリルマレイミド、N−ステアリルマレイミド、N−2−エチルヘキシルマレイミド、N−2−デシルテトラデシルマレイミドが好ましい。なお、(a)単位を構成するための上記単量体は単独で使用してもよいし、2種以上を併用してもよい。 Specific examples of the maleimide-based monomer include, for example, N-octylmaleimide, N-2-ethylhexylmaleimide, N-decylmaleimide, N-laurylmaleimide, N-tetradecylmaleimide, N-stearylmaleimide, N-2-. Decyl tetradecyl maleimide and the like can be mentioned. Among these, N-lauryl maleimide, N-stearyl maleimide, N-2-ethylhexyl maleimide, and N-2-decyl tetradecyl maleimide are preferable from the viewpoints of availability and economy and high solubility in base oil. The above monomers for constituting the unit (a) may be used alone or in combination of two or more kinds.
(a)単位の含有量は、該重合体100質量部に対して、5質量部以上が好ましく、また65質量部以下が好ましく、50質量部以下がより好ましく、40質量部以下がさらに好ましい。上記範囲の(a)単位を有する粘度指数向上剤は、窒素原子上の有機基の効果により基油への溶解性を高めることができるとともに、主鎖の環構造によりせん断安定性や耐熱性を高めることができる。さらには、スラッジ等の清浄分散性の向上や金属表面の摩耗抑制等の効果が期待される。 The content of the (a) unit is preferably 5 parts by mass or more, more preferably 65 parts by mass or less, more preferably 50 parts by mass or less, and further preferably 40 parts by mass or less, relative to 100 parts by mass of the polymer. The viscosity index improver having the unit (a) in the above range can improve the solubility in the base oil due to the effect of the organic group on the nitrogen atom, and at the same time, can improve the shear stability and the heat resistance due to the ring structure of the main chain. Can be increased. Further, effects such as improvement of clean dispersibility of sludge and the like and suppression of wear of metal surface are expected.
本発明の粘度指数向上剤に含まれる重合体は、前記(a)単位に加え、炭素数が6〜40の脂肪族炭化水素基を有するアルキル(メタ)アクリレート由来の(b)単位と炭素数が1〜5の脂肪族炭化水素基を有するアルキル(メタ)アクリレート由来の(c)単位を有することが好ましい。
(b)単位を構成するためには、下記一般式(2)で表されるアルキル(メタ)アクリレートを重合することが好ましい。下記一般式(2)中、R3は水素原子又はメチル基を表し、R4は炭素数6〜40のアルキル基(好ましくは炭素数6〜24のアルキル基であり、より好ましくは炭素数12〜24のアルキル基)を表す。R4のアルキル基は、鎖状、環状、分岐状のいずれであってもよく、置換基を有していてもよい。
The polymer contained in the viscosity index improver of the present invention includes, in addition to the (a) unit, a (b) unit derived from an alkyl (meth) acrylate having an aliphatic hydrocarbon group having 6 to 40 carbon atoms and a carbon number. Preferably has a unit (c) derived from an alkyl (meth) acrylate having 1 to 5 aliphatic hydrocarbon groups.
In order to form the unit (b), it is preferable to polymerize an alkyl (meth) acrylate represented by the following general formula (2). In the following general formula (2), R 3 represents a hydrogen atom or a methyl group, R 4 represents an alkyl group having 6 to 40 carbon atoms (preferably an alkyl group having 6 to 24 carbon atoms, and more preferably 12 carbon atoms). ~ 24 alkyl groups). The alkyl group for R 4 may be linear, cyclic, or branched, and may have a substituent.
一般式(2)で表される(メタ)アクリレートは、R3及びR4がそれぞれ単一の単量体であってもよく、R3及び/又はR4が異なる2種以上の単量体の混合物であってもよい。反応性の点から、R3は水素原子又はメチル基であることが好ましい。 In the (meth) acrylate represented by the general formula (2), R 3 and R 4 may each be a single monomer, or two or more kinds of R 3 and / or R 4 different from each other. It may be a mixture of. From the viewpoint of reactivity, R 3 is preferably a hydrogen atom or a methyl group.
一般式(2)で表されるアルキル(メタ)アクリレートの具体例としては、例えば、n−ヘキシル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、n−オクチル(メタ)アクリレート、ノニル(メタ)アクリレート、デシル(メタ)アクリレート、ウンデシル(メタ)アクリレート、ラウリル(メタ)アクリレート、トリデシル(メタ)アクリレート、テトラデシル(メタ)アクリレート、ペンタデシル(メタ)アクリレート、ヘキサデシル(メタ)アクリレート、ヘプタデシル(メタ)アクリレート、ステアリル(メタ)アクリレート、ノナデシル(メタ)アクリレート、エイコシル(メタ)アクリレート、ベヘニル(メタ)アクリレート、テトラコシル(メタ)アクリレート、2−デシルテトラデシル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、メンチル(メタ)アクリレート、イソボルニル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、アダマンチル(メタ)アクリレート等が挙げられる。なかでも、入手性や経済性の観点および基油への溶解性が高いことから、2−エチルヘキシル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、エイコシル(メタ)アクリレート、ベヘニル(メタ)アクリレート、テトラコシル(メタ)アクリレート、2−デシルテトラデシル(メタ)アクリレート、シクロヘキシル(メタ)アクリレートが好ましい。上記一般式(2)で表される(メタ)アクリレートは単独で使用してもよいし、2種以上を併用してもよい。 Specific examples of the alkyl (meth) acrylate represented by the general formula (2) include, for example, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, nonyl (meth). Acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, Stearyl (meth) acrylate, nonadecyl (meth) acrylate, eicosyl (meth) acrylate, behenyl (meth) acrylate, tetracosyl (meth) acrylate, 2-decyltetradecyl (meth) acrylate Over DOO, cyclohexyl (meth) acrylate, menthyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, adamantyl (meth) acrylate. Among them, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, eicosyl (meth) acrylate, behenyl (behenyl (from the viewpoints of availability and economical efficiency and high solubility in base oil). Preferred are (meth) acrylate, tetracosyl (meth) acrylate, 2-decyltetradecyl (meth) acrylate, and cyclohexyl (meth) acrylate. The (meth) acrylate represented by the general formula (2) may be used alone or in combination of two or more kinds.
一般式(2)で表される(メタ)アクリレートの含有量は、該重合体100質量部に対して、20質量部以上が好ましく、40質量部以上がより好ましく、また90質量部未満が好ましく、80質量部以下がより好ましく、70質量部以下がさらに好ましい。上記数値範囲の(b)単位を有する重合体を含む粘度指数向上剤は、種々の組成の基油への溶解性が良好なものとなる。
(c)単位を構成するためには、下記一般式(3)で表されるアルキル(メタ)アクリレートを重合することが好ましい。下記一般式(3)中、R5は水素原子又はメチル基を表し、R6は炭素数1〜5の脂肪族炭化水素基(好ましくは炭素数1〜5のアルキル基)を表す。なお、R6の脂肪族炭化水素基は直鎖状、環状、分岐状のいずれであってもよく、置換基を有していてもよい。
The content of the (meth) acrylate represented by the general formula (2) is preferably 20 parts by mass or more, more preferably 40 parts by mass or more, and less than 90 parts by mass with respect to 100 parts by mass of the polymer. , 80 parts by mass or less is more preferable, and 70 parts by mass or less is further preferable. The viscosity index improver containing the polymer having the unit (b) in the above numerical range has good solubility in base oils of various compositions.
In order to form the unit (c), it is preferable to polymerize an alkyl (meth) acrylate represented by the following general formula (3). In the following general formula (3), R 5 represents a hydrogen atom or a methyl group, and R 6 represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms (preferably an alkyl group having 1 to 5 carbon atoms). The aliphatic hydrocarbon group for R 6 may be linear, cyclic, or branched, and may have a substituent.
一般式(3)で表されるアルキル(メタ)アクリレートは、R5及びR6がそれぞれ単一の単量体であってもよく、R5及び/又はR6が異なる2種以上の単量体の混合物であってもよい。反応性の点から、R5は水素原子又はメチル基であることが好ましい。また、粘度指数向上の点から、R6の脂肪族炭化水素基は直鎖状または分岐状であることが好ましい。 In the alkyl (meth) acrylate represented by the general formula (3), R 5 and R 6 may each be a single monomer, and R 5 and / or R 6 are different from each other as a single monomer. It may be a mixture of bodies. From the viewpoint of reactivity, R 5 is preferably a hydrogen atom or a methyl group. From the viewpoint of improving the viscosity index, the aliphatic hydrocarbon group for R 6 is preferably linear or branched.
一般式(3)で表されるアルキル(メタ)アクリレートの具体例としては、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、n−プロピル(メタ)アクリレート、iso−プロピル(メタ)アクリレート、n−ブチル(メタ)アクリレート、iso−ブチル(メタ)アクリレート、t−ブチル(メタ)アクリレート、n−アミル(メタ)アクリレート、iso−アミル(メタ)アクリレート、t−アミル(メタ)アクリレート、ネオペンチル(メタ)アクリレート等が挙げられる。中でも、一般式(3)で表される(メタ)アクリレートとして、少なくともメチル(メタ)アクリレートを含むことが好ましい。一般式(3)で表される(メタ)アクリレートがメチル(メタ)アクリレートを含有することにより、粘度指数向上効果が大きく、耐熱性およびせん断安定性が高い粘度指数向上剤となる。上記一般式(3)で表される(メタ)アクリレートは単独で使用してもよいし、2種以上を併用してもよい。 Specific examples of the alkyl (meth) acrylate represented by the general formula (3) include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, iso-propyl (meth) acrylate, n-butyl (meth) acrylate, iso-butyl (meth) acrylate, t-butyl (meth) acrylate, n-amyl (meth) acrylate, iso-amyl (meth) acrylate, t-amyl (meth) acrylate, neopentyl ( Examples thereof include (meth) acrylate. Above all, it is preferable that at least methyl (meth) acrylate is contained as the (meth) acrylate represented by the general formula (3). When the (meth) acrylate represented by the general formula (3) contains methyl (meth) acrylate, the viscosity index improving effect is large, and the viscosity index improving agent has high heat resistance and shear stability. The (meth) acrylate represented by the general formula (3) may be used alone or in combination of two or more kinds.
(c)単位の含有量は、該重合体100質量部に対して、5質量部以上が好ましく、10量部以上がより好ましく、また40質量部以下が好ましく、35質量部以下がより好ましく、30質量部以下がさらに好ましい。(c)単位の含有量が上記範囲であれば、他の成分との共重合性が良く、重合速度も良好で重合率も高く生産性が良い。また、共重合して得られる粘度指数向上剤のせん断安定性や基油溶解性がより良好となる。 The content of the unit (c) is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and preferably 40 parts by mass or less, more preferably 35 parts by mass or less, with respect to 100 parts by mass of the polymer. It is more preferably 30 parts by mass or less. When the content of the unit (c) is within the above range, the copolymerizability with other components is good, the polymerization rate is good, the polymerization rate is high, and the productivity is good. Further, the shear stability and base oil solubility of the viscosity index improver obtained by copolymerization become better.
本発明の粘度指数向上剤に含まれる重合体は、前記重合体100質量部に対し、(a)単位の量および(c)単位の量の合計が、30質量部以上であることが好ましく、40質量部以上であることがより好ましく、また95質量部未満であることが好ましく、80質量部未満であることがより好ましい。(a)単位の量および(c)単位の量の合計が上記範囲であれば、基油への溶解性を確保しながら、主鎖の環構造による高いせん断安定性と(c)単位による高い粘度指数を両立することができる。 The polymer contained in the viscosity index improver of the present invention preferably has a total amount of (a) units and (c) units of 30 parts by mass or more based on 100 parts by mass of the polymer. It is more preferably 40 parts by mass or more, preferably less than 95 parts by mass, and more preferably less than 80 parts by mass. When the total amount of the (a) unit and the total amount of the (c) unit are in the above-mentioned ranges, high shear stability due to the ring structure of the main chain and high due to the (c) unit are ensured while ensuring solubility in the base oil. Viscosity index can be compatible.
本発明の粘度指数向上剤に含まれる重合体において、(a)単位と(c)単位の質量比は、前者/後者がたとえば65/5〜5/40、好ましくは50/10〜5/35、より好ましくは40/10〜5/30である。(a)単位と(c)単位の質量比が上記範囲であれば、基油への溶解性を確保しながら、主鎖の環構造による高いせん断安定性と(c)単位による高い粘度指数を両立することができる。 In the polymer contained in the viscosity index improver of the present invention, the mass ratio of the (a) unit and the (c) unit is, for example, 65/5 to 5/40, preferably 50/10 to 5/35 for the former / the latter. , And more preferably 40/10 to 5/30. When the mass ratio of the (a) unit to the (c) unit is in the above range, high shear stability due to the ring structure of the main chain and high viscosity index due to the (c) unit are ensured while ensuring solubility in the base oil. Can be compatible.
本発明の重合体は、一般式(1)で示される(a)単位、一般式(2)で表されるアルキル(メタ)アクリレート由来の(b)単位、一般式(3)で表されるアルキル(メタ)アクリレート由来の(c)単位以外の単位(以下、「(d)単位」と称する)を含有することができる。(a)、(b)、(c)、(d)単位を構成するためにはラジカル重合が生産性やコストの観点から有利である。ラジカル重合性単量体は、ラジカル重合性基を同一分子内に1個有する単官能単量体と、ラジカル重合性基を同一分子内に2個以上有する多官能単量体とに分類できる。 The polymer of the present invention is represented by a unit (a) represented by the general formula (1), a unit (b) derived from an alkyl (meth) acrylate represented by the general formula (2), and a general formula (3). A unit other than the unit (c) derived from alkyl (meth) acrylate (hereinafter, referred to as “(d) unit”) can be contained. Radical polymerization is advantageous in terms of productivity and cost in order to form units (a), (b), (c), and (d). The radical-polymerizable monomer can be classified into a monofunctional monomer having one radical-polymerizable group in the same molecule and a polyfunctional monomer having two or more radical-polymerizable groups in the same molecule.
(d)単位を構成するための単官能単量体の例としては、一般式(2)、(3)以外のその他の(メタ)アクリレート、不飽和モノまたはジカルボン酸エステル、不飽和カルボン酸類、ビニル芳香族化合物、ビニルエステル、ビニルエーテル、オレフィン類、シアン化ビニル、N−ビニル化合物等が挙げられる。これらの単官能単量体は、それぞれ単独で用いてもよく、2種類以上を併用してもよい。 Examples of the monofunctional monomer for forming the unit (d) include (meth) acrylates other than the general formulas (2) and (3), unsaturated mono- or dicarboxylic acid esters, unsaturated carboxylic acids, Examples thereof include vinyl aromatic compounds, vinyl esters, vinyl ethers, olefins, vinyl cyanide, N-vinyl compounds and the like. These monofunctional monomers may be used alone or in combination of two or more kinds.
一般式(2)、(3)以外のその他の(メタ)アクリレートとしては、例えば、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、2−メトキシエチル(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、N,N−ジメチルアミノエチル(メタ)アクリレート、モルフォリノアルキレン(メタ)アクリレート、α−ヒドロキシメチルアクリル酸メチル、ポリエチレングリコールモノ(メタ)アクリレート等が挙げられる。 Examples of other (meth) acrylates other than the general formulas (2) and (3) include 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, and tetrahydro. Furfuryl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, morpholinoalkylene (meth) acrylate, methyl α-hydroxymethylacrylate, polyethylene glycol mono (meth) acrylate and the like can be mentioned.
不飽和モノまたはジカルボン酸エステルとしては、例えば、ブチルクロトネート、オクチルクロトネート、ジブチルマレエート、ジラウリルマレエート、ジオクチルフマレート、ジステアリルフマレート、等が挙げられる。 Examples of unsaturated mono- or dicarboxylic acid esters include butyl crotonate, octyl crotonate, dibutyl maleate, dilauryl maleate, dioctyl fumarate, distearyl fumarate, and the like.
不飽和カルボン酸類としては、例えば、(メタ)アクリル酸、マレイン酸、フマル酸、無水マレイン酸、N−置換マレイミド等が挙げられる。 Examples of unsaturated carboxylic acids include (meth) acrylic acid, maleic acid, fumaric acid, maleic anhydride, and N-substituted maleimides.
ビニル芳香族化合物としては、例えば、スチレン、α−メチルスチレン、ビニルトルエン、メトキシスチレン等のスチレン系単量体、2−ビニルピリジン、4−ビニルピリジン等が挙げられる。 Examples of the vinyl aromatic compound include styrene-based monomers such as styrene, α-methylstyrene, vinyltoluene, and methoxystyrene, 2-vinylpyridine, 4-vinylpyridine, and the like.
ビニルエステルとしては、例えば、酢酸ビニル、プロピオン酸ビニル、オクチル酸ビニル等が挙げられる。 Examples of the vinyl ester include vinyl acetate, vinyl propionate, vinyl octylate and the like.
ビニルエーテルとしては、例えば、メチルビニルエーテル、ブチルビニルエーテル、オクチルビニルエーテル、ドデシルビニルエーテル、等が挙げられる。 Examples of vinyl ethers include methyl vinyl ether, butyl vinyl ether, octyl vinyl ether, dodecyl vinyl ether, and the like.
オレフィン類としては、エチレン、プロピレン、1−ブテン、イソブテン、1−テトラデセン、1−オクタデセン、ジイソブテン等が挙げられる。 Examples of the olefins include ethylene, propylene, 1-butene, isobutene, 1-tetradecene, 1-octadecene, diisobutene and the like.
シアン化ビニルとしては、例えば、アクリロニトリル、メタクリロニトリル等が挙げられる。 Examples of vinyl cyanide include acrylonitrile and methacrylonitrile.
N−ビニル化合物としては、例えば、N−ビニルピロリドン、N−ビニルカプロラクタム、N−ビニルイミダゾール、N−ビニルモルフォリン、N−ビニルアセトアミド等が挙げられる。 Examples of the N-vinyl compound include N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylimidazole, N-vinylmorpholine, N-vinylacetamide and the like.
これらの単官能単量体のうち、2−ヒドロキシエチル(メタ)アクリレート、N,N−ジメチルアミノエチル(メタ)アクリレート、α−ヒドロキシメチルアクリル酸メチル、N−ビニルピロリドンが好ましい。 Among these monofunctional monomers, 2-hydroxyethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, methyl α-hydroxymethylacrylate, and N-vinylpyrrolidone are preferable.
(d)単位を構成するための単官能単量体は、該重合体100質量部に対して、0質量部以上30質量部以下が好ましく、25質量部以下がより好ましく、20質量部以下がさらに好ましい。 The monofunctional monomer for constituting the unit (d) is preferably 0 parts by mass or more and 30 parts by mass or less, more preferably 25 parts by mass or less, and 20 parts by mass or less with respect to 100 parts by mass of the polymer. More preferable.
(d)単位を構成するための多官能単量体の例としては、多官能(メタ)アクリレート、ビニルエーテル基含有(メタ)アクリレート、アリル基含有(メタ)アクリレート、多官能(メタ)アクリロイル基含有イソシアヌレート、多官能ウレタン(メタ)アクリレートなどの多官能(メタ)アクリル系化合物、多官能マレイミド系化合物、多官能ビニルエーテル、多官能アリル系化合物、多官能芳香族ビニルなどが挙げられる。上記多官能単量体は単独で使用してもよいし、2種以上を併用してもよい。 Examples of the polyfunctional monomer for forming the unit (d) include polyfunctional (meth) acrylate, vinyl ether group-containing (meth) acrylate, allyl group-containing (meth) acrylate, and polyfunctional (meth) acryloyl group-containing. Examples thereof include polyfunctional (meth) acrylic compounds such as isocyanurate and polyfunctional urethane (meth) acrylate, polyfunctional maleimide compounds, polyfunctional vinyl ethers, polyfunctional allyl compounds, and polyfunctional aromatic vinyls. The above polyfunctional monomers may be used alone or in combination of two or more.
多官能(メタ)アクリレート(多官能(メタ)アクリル酸エステル)としては、例えば、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、ヘキサンジオールジ(メタ)アクリレート、ビスフェノールAアルキレンオキシドジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、2,2’−〔オキシビス(メチレン)〕ビスアクリル酸、ジアルキル−2,2’−〔オキシビス(メチレン)〕ビス−2−プロペノエート等が挙げられる。 Examples of the polyfunctional (meth) acrylate (polyfunctional (meth) acrylic acid ester) include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, hexanediol di (meth). Acrylate, bisphenol A alkylene oxide di (meth) acrylate, trimethylolpropane tri (meth) acrylate, 2,2 '-[oxybis (methylene)] bisacrylic acid, dialkyl-2,2'-[oxybis (methylene)] bis -2-Propenoate etc. are mentioned.
ビニルエーテル基含有(メタ)アクリレート(ビニルエーテル基含有(メタ)アクリル酸エステル)としては、例えば、(メタ)アクリル酸2−ビニロキシエチル、(メタ)アクリル酸4−ビニロキシブチル、(メタ)アクリル酸2−(ビニロキシエトキシ)エチル等が挙げられる。 Examples of the vinyl ether group-containing (meth) acrylate (vinyl ether group-containing (meth) acrylic acid ester) include 2-vinyloxyethyl (meth) acrylate, 4-vinyloxybutyl (meth) acrylate, and 2- (vinyl chloride) (meth) acrylate. Roxyethoxy) ethyl and the like can be mentioned.
アリル基含有(メタ)アクリレート(アリル基含有(メタ)アクリル酸エステル)としては、例えば、(メタ)アクリル酸アリル、α−アリルオキシメチルアクリル酸メチル、α−アリルオキシメチルアクリル酸ステアリル、α−アリルオキシメチルアクリル酸2−デシルテトラデシル等が挙げられる。 Examples of the allyl group-containing (meth) acrylate (allyl group-containing (meth) acrylic acid ester) include allyl (meth) acrylate, α-allyloxymethyl methyl acrylate, α-allyloxymethyl acrylic acid stearyl, α- 2-decyl tetradecyl allyloxymethyl acrylate etc. are mentioned.
多官能(メタ)アクリロイル基含有イソシアヌレートとしては、例えば、トリ(アクリロイルオキシエチル)イソシアヌレート、トリ(メタクリロイルオキシエチル)イソシアヌレート等が挙げられる。 Examples of the polyfunctional (meth) acryloyl group-containing isocyanurate include tri (acryloyloxyethyl) isocyanurate and tri (methacryloyloxyethyl) isocyanurate.
多官能ウレタン(メタ)アクリレート(多官能ウレタン(メタ)アクリル酸エステル)としては、例えば、トリレンジイソシアネート、イソホロンジイソシアネート、キシリレンジイソシアネート等の多官能イソシアネートと(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピル等の水酸基含有(メタ)アクリル酸エステルとの反応で得られる多官能ウレタン(メタ)アクリレート等が挙げられる。 Examples of the polyfunctional urethane (meth) acrylate (polyfunctional urethane (meth) acrylic acid ester) include polyfunctional isocyanates such as tolylene diisocyanate, isophorone diisocyanate, and xylylene diisocyanate, and 2-hydroxyethyl (meth) acrylate, ( Examples thereof include polyfunctional urethane (meth) acrylates obtained by reaction with a hydroxyl group-containing (meth) acrylic acid ester such as 2-hydroxypropyl (meth) acrylate.
多官能マレイミド系化合物としては、例えば、4,4’−ジフェニルメタンビスマレイミド、m−フェニレンビスマレイミド、ビスフェノールAジフェニルエーテルビスマレイミド、1,6−ビスマレイミド−(2,2,4−トリメチル)ヘキサン等が挙げられる。 Examples of the polyfunctional maleimide compound include 4,4′-diphenylmethane bismaleimide, m-phenylene bismaleimide, bisphenol A diphenyl ether bismaleimide, and 1,6-bismaleimide- (2,2,4-trimethyl) hexane. Can be mentioned.
多官能ビニルエーテルとしては、例えば、エチレングリコールジビニルエーテル、ジエチレングリコールジビニルエーテル、ポリエチレングリコールジビニルエーテル、ヘキサンジオールジビニルエーテル、ビスフェノールAアルキレンオキシドジビニルエーテル、トリメチロールプロパントリビニルエーテル等が挙げられる。 Examples of polyfunctional vinyl ethers include ethylene glycol divinyl ether, diethylene glycol divinyl ether, polyethylene glycol divinyl ether, hexanediol divinyl ether, bisphenol A alkylene oxide divinyl ether, trimethylolpropane trivinyl ether, and the like.
多官能アリル系化合物としては、例えば、エチレングリコールジアリルエーテル、ジエチレングリコールジアリルエーテル、ポリエチレングリコールジアリルエーテル、ヘキサンジオールジアリルエーテル、ビスフェノールAアルキレンオキシドジアリルエーテル、トリメチロールプロパントリアリルエーテル、ジトリメチロールプロパンテトラアリルエーテル等の多官能アリルエーテル;トリアリルイソシアヌレート等の多官能アリル基含有イソシアヌレート;フタル酸ジアリル、ジフェン酸ジアリル等の多官能アリルエステル;ビスアリルナジイミド化合物等;ビスアリルナジイミド化合物等が挙げられる。 Examples of polyfunctional allyl compounds include ethylene glycol diallyl ether, diethylene glycol diallyl ether, polyethylene glycol diallyl ether, hexanediol diallyl ether, bisphenol A alkylene oxide diallyl ether, trimethylolpropane triallyl ether, and ditrimethylolpropane tetraallyl ether. Polyfunctional allyl ethers; polyfunctional allyl group-containing isocyanurates such as triallyl isocyanurate; polyfunctional allyl esters such as diallyl phthalate and diallyl diphenate; bisallylnadiimide compounds and the like; bisallylnadiimide compounds and the like. .
多官能芳香族ビニルとしては、例えば、ジビニルベンゼン等が挙げられる。 Examples of the polyfunctional aromatic vinyl include divinylbenzene and the like.
(d)単位を構成するための多官能単量体の含有量は、全単量体成分の合計100質量部に対して、0質量部以上5質量部以下が好ましく、3質量部以下がより好ましく、2質量部以下がさらに好ましい。また、重合体中の多官能単量体由来の単位の含有量は、重合体100質量部に対して、0質量部以上5質量部以下であることが好ましく、3質量部以下がより好ましく、2質量部以下がさらに好ましい。この場合、重合体が分岐構造などをとることにより、基油への溶解性を大きく損ねることなく、該重合体を含有する粘度指数向上剤のせん断安定性を改善することができる。 The content of the polyfunctional monomer for constituting the unit (d) is preferably 0 parts by mass or more and 5 parts by mass or less, and more preferably 3 parts by mass or less with respect to 100 parts by mass in total of all the monomer components. It is preferably 2 parts by mass or less and more preferably 2 parts by mass or less. The content of the polyfunctional monomer-derived unit in the polymer is preferably 0 parts by mass or more and 5 parts by mass or less, more preferably 3 parts by mass or less, with respect to 100 parts by mass of the polymer. It is more preferably 2 parts by mass or less. In this case, the polymer having a branched structure can improve the shear stability of the viscosity index improver containing the polymer without significantly impairing the solubility in the base oil.
ただし、2,2’−〔オキシビス(メチレン)〕ビスアクリル酸、ジアルキル−2,2’−〔オキシビス(メチレン)〕ビス−2−プロペノエート、α―アリルオキシメチルアクリル酸メチル、α−アリルオキシメチルアクリル酸ステアリル、α−アリルオキシメチルアクリル酸2−デシルテトラデシルのように、環化しながら重合が進行する多官能単量体の場合は、重合体中の多官能単量体由来の単位の含有量は、重合体100質量部に対して、0質量部以上30質量部以下であることが好ましく、25質量部以下がより好ましく、20質量部以下がさらに好ましい。全単量体成分の合計100質量部に対する多官能単量体の含有量も同様である。この場合、主鎖に導入される環構造の効果により、該重合体を含有する粘度指数向上剤の耐熱性が向上するとともに、せん断安定性を改善することができる。 However, 2,2 '-[oxybis (methylene)] bisacrylic acid, dialkyl-2,2'-[oxybis (methylene)] bis-2-propenoate, methyl α-allyloxymethyl acrylate, α-allyloxymethyl In the case of a polyfunctional monomer in which polymerization proceeds while cyclizing, such as stearyl acrylate and 2-decyltetradecyl α-allyloxymethyl acrylate, the inclusion of a unit derived from the polyfunctional monomer in the polymer. The amount is preferably 0 parts by mass or more and 30 parts by mass or less, more preferably 25 parts by mass or less, and further preferably 20 parts by mass or less with respect to 100 parts by mass of the polymer. The same applies to the content of the polyfunctional monomer based on 100 parts by mass of all the monomer components. In this case, due to the effect of the ring structure introduced into the main chain, the heat resistance of the viscosity index improver containing the polymer can be improved and the shear stability can be improved.
多官能単量体由来の単位が上記範囲を超えると、重合時にゲル化が進行したり、該重合体を含有する粘度指数向上剤の基油への溶解度が低下したりする場合がある。 When the unit derived from the polyfunctional monomer exceeds the above range, gelation may proceed during polymerization, or the solubility of the viscosity index improver containing the polymer in the base oil may decrease.
上記単量体成分をラジカル重合機構により重合する場合、ラジカル重合開始剤を併用するのが工業的に有利で好ましい。ラジカル重合開始剤としては、加熱により重合開始ラジカルを発生する熱ラジカル重合開始剤と、活性エネルギー線の照射により重合開始ラジカルを発生する光ラジカル重合開始剤とがあり、従来公知のものを1種または2種以上使用できる。また、必要に応じて従来公知の熱ラジカル重合促進剤、光増感剤、光ラジカル重合促進剤等を1種または2種以上添加することも好ましい。 When the above monomer component is polymerized by a radical polymerization mechanism, it is industrially advantageous and preferable to use a radical polymerization initiator in combination. As the radical polymerization initiator, there are a thermal radical polymerization initiator that generates a polymerization initiation radical by heating and a photoradical polymerization initiator that generates a polymerization initiation radical by irradiation with an active energy ray. Alternatively, two or more kinds can be used. Further, if necessary, it is also preferable to add one or more conventionally known thermal radical polymerization accelerators, photosensitizers, photoradical polymerization accelerators, and the like.
上記熱ラジカル重合開始剤としては、具体的には、例えば、メチルエチルケトンパーオキサイド、シクロヘキサノンパーオキサイド、メチルシクロヘキサノンパーオキサイド、メチルアセトアセテートパーオキサイド、アセチルアセテートパーオキサイド、1,1−ビス(t−ヘキシルパーオキシ)−3,3,5−トリメチルシクロヘキサン、1,1−ビス(t−ヘキシルパーオキシ)シクロヘキサン、1,1−ビス(t−ブチルパーオキシ)−3,3,5−トリメチルシクロヘキサン、1,1−ビス(t−ブチルパーオキシ)−2−メチルシクロヘキサン、1,1−ビス(t−ブチルパーオキシ)シクロヘキサン、1,1−ビス(t−ブチルパーオキシ)シクロドデカン、1,1−ビス(t−ブチルパーオキシ)ブタン、p−メンタンハイドロパーオキサイド、ジイソプロピルベンゼンハイドロパーオキサイド、1,1,3,3−テトラメチルブチルハイドロパーオキサイド、クメンハイドロパーオキサイド、t−ヘキシルハイドロパーオキサイド、t−ブチルハイドロパーオキサイド、α,α’−ビス(t−ブチルパーオキシ)ジイソプロピルベンゼン、ジクミルパーオキサイド、2,5−ジメチル−2,5−ビス(t−ブチルパーオキシ)ヘキサン、t−ブチルクミルパーオキサイド、ジ−t−ブチルパーオキサイド、2,5−ジメチル−2,5−ビス(t−ブチルパーオキシ)ヘキシン−3、イソブチリルパーオキサイド、3,5,5−トリメチルヘキサノイルパーオキサイド、オクタノイルパーオキサイド、ラウロイルパーオキサイド、ステアロイルパーオキサイド、スクシン酸パーオキサイド、m−トルオイルベンゾイルパーオキサイド、ベンゾイルパーオキサイド、ジ−n−プロピルパーオキシジカーボネート、ジイソプロピルパーオキシジカーボネート、ビス(4−t−ブチルシクロヘキシル)パーオキシジカーボネート、ジ−2−エトキシエチルパーオキシジカーボネート、ジ−2−エトキシヘキシルパーオキシジカーボネート、ジ−3−メトキシブチルパーオキシジカーボネート、ジ−s−ブチルパーオキシジカーボネート、ジ(3−メチル−3−メトキシブチル)パーオキシジカーボネート、α,α’−ビス(ネオデカノイルパーオキシ)ジイソプロピルベンゼン、クミルパーオキシネオデカノエート、1,1,3,3,−テトラメチルブチルパーオキシネオデカノエート、1−シクロヘキシル−1−メチルエチルパーオキシネオデカノエート、t−ヘキシルパーオキシネオデカノエート、t−ブチルパーオキシネオデカノエート、t−ヘキシルパーオキシピバレート、t−ブチルパーオキシピバレート、1,1,3,3−テトラメチルブチルパーオキシ−2−エチルヘキサノエート、2,5−ジメチル−2,5−ビス(2−エチルヘキサノイルパーオキシ)ヘキサノエート、1−シクロヘキシル−1−メチルエチルパーオキシ−2−エチルヘキサノエート、t−ヘキシルパーオキシ−2−エチルヘキサノエート、t−ブチルパーオキシ−2−エチルヘキサノエート、t−ヘキシルパーオキシイソプロピルモノカーボネート、t−ブチルパーオキシイソブチレート、t−ブチルパーオキシマレート、t−ブチルパーオキシ−3,5,5−トリメチルヘキサノエート、t−ブチルパーオキシラウレート、t−ブチルパーオキシイソプロピルモノカーボネート、t−ブチルパーオキシ−2−エチルヘキシルモノカーボネート、t−ブチルパーオキシアセテート、t−ブチルパーオキシ−m−トルイルベンゾエート、t−ブチルパーオキシベンゾエート、ビス(t−ブチルパーオキシ)イソフタレート、2,5−ジメチル−2,5−ビス(m−トルイルパーオキシ)ヘキサン、t−ヘキシルパーオキシベンゾエート、2,5−ジメチル−2,5−ビス(ベンゾイルパーオキシ)ヘキサン、t−ブチルパーオキシアリルモノカーボネート、t−ブチルトリメチルシリルパーオキサイド、2,2−ビス(4,4−ジ−t−ブチルパーオキシシクロヘキシル)プロパン、3,3’,4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン、t−アミルパーオキシイソナノエート、t−アミルパーオキシ−2−エチルヘキサノエート、過硫酸ナトリウム、過硫酸カリウム、過硫酸アンモニウム、過酸化水素等の過酸化物系開始剤;2−フェニルアゾ−4−メトキシ−2,4−ジメチルバレロニトリル、1−[(1−シアノ−1−メチルエチル)アゾ]ホルムアミド、1,1’−アゾビス(シクロヘキサン−1−カルボニトリル)、2,2’−アゾビス(2−メチルブチロニトリル)、2,2’−アゾビスイソブチロニトリル、2,2’−アゾビス(2,4−ジメチルバレロニトリル)、2,2’−アゾビス(2,4−ジメチル−4−メトキシバレロニトリル)、2,2’−アゾビス(2−メチルプロピオンアミジン)ジヒドロクロリド、2,2’−アゾビス(2−メチル−N−フェニルプロピオンアミジン)ジヒドロクロリド、2,2’−アゾビス[N−(4−クロロフェニル)−2−メチルプロピオンアミジン]ジヒドロクロリド、2,2’−アゾビス[N−(4−ヒドロフェニル)−2−メチルプロピオンアミジン]ジヒドロクロリド、2,2’−アゾビス[2−メチル−N−(フェニルメチル)プロピオンアミジン]ジヒドロクロリド、2,2’−アゾビス[2−メチル−N−(2−プロペニル)プロピオンアミジン]ジヒドロクロリド、2,2’−アゾビス[N−(2−ヒドロキシエチル)−2−メチルプロピオンアミジン]ジヒドロクロリド、2,2’−アゾビス[2−(5−メチル−2−イミダゾリン−2−イル)プロパン]ジヒドロクロリド、2,2’−アゾビス[2−(2−イミダゾリン−2−イル)プロパン]ジヒドロクロリド、2,2’−アゾビス[2−(4,5,6,7−テトラヒドロ−1H−1,3−ジアゼピン−2−イル)プロパン]ジヒドロクロリド、2,2’−アゾビス[2−(3,4,5,6−テトラヒドロピリミジン−2−イル)プロパン]ジヒドロクロリド、2,2’−アゾビス[2−(5−ヒドロキシ−3,4,5,6−テトラヒドロピリミジン−2−イル)プロパン]ジヒドロクロリド、2,2’−アゾビス{2−[1−(2−ヒドロキシエチル)−2−イミダゾリン−2−イル]プロパン}ジヒドロクロリド、2,2’−アゾビス[2−(2−イミダゾリン−2−イル)プロパン]、2,2’−アゾビス{2−メチル−N−[1,1−ビス(ヒドロキシメチル)−2−ヒドロキシエチル]プロピオンアミド}、2,2’−アゾビス{2−メチル−N−[1,1−ビス(ヒドロキシメチル)エチル]プロピオンアミド}、2,2’−アゾビス[2−メチル−N−(2−ヒドロキシエチル)プロピオンアミド]、2,2’−アゾビス(2−メチルプロピオンアミド)、2,2’−アゾビス(2,4,4−トリメチルペンタン)、2,2’−アゾビス(2−メチルプロパン)、ジメチル−2,2−アゾビス(2−メチルプロピオネート)、4,4’−アゾビス(4−シアノペンタン酸)、2,2’−アゾビス[2−(ヒドロキシメチル)プロピオニトリル]等のアゾ系開始剤、2,3−ジメチル−2,3−ジフェニルブタン等が挙げられる。 Specific examples of the thermal radical polymerization initiator include methyl ethyl ketone peroxide, cyclohexanone peroxide, methyl cyclohexanone peroxide, methyl acetoacetate peroxide, acetyl acetate peroxide, and 1,1-bis (t-hexylperoxide). Oxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-hexylperoxy) cyclohexane, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1, 1-bis (t-butylperoxy) -2-methylcyclohexane, 1,1-bis (t-butylperoxy) cyclohexane, 1,1-bis (t-butylperoxy) cyclododecane, 1,1-bis (T-Butylperoxy) butane, p-menthane high Loperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-hexyl hydroperoxide, t-butyl hydroperoxide, α, α′-bis (T-butylperoxy) diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexane, t-butylcumyl peroxide, di-t-butylperoxide, 2,5-Dimethyl-2,5-bis (t-butylperoxy) hexyne-3, isobutyryl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearoyl peroxide Oxide Acid peroxide, m-toluoyl benzoyl peroxide, benzoyl peroxide, di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, di-2 -Ethoxyethyl peroxydicarbonate, di-2-ethoxyhexyl peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-s-butyl peroxydicarbonate, di (3-methyl-3-methoxybutyl) ) Peroxydicarbonate, α, α′-bis (neodecanoylperoxy) diisopropylbenzene, cumylperoxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, 1 -Cyclohexyl-1- Cylethyl peroxy neodecanoate, t-hexyl peroxy neodecanoate, t-butyl peroxy neodecanoate, t-hexyl peroxypivalate, t-butyl peroxypivalate, 1,1,3 , 3-Tetramethylbutylperoxy-2-ethylhexanoate, 2,5-Dimethyl-2,5-bis (2-ethylhexanoylperoxy) hexanoate, 1-Cyclohexyl-1-methylethylperoxy-2 -Ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-hexylperoxyisopropylmonocarbonate, t-butylperoxyisobutyrate, t-butyl peroxymalate, t-butyl peroxy-3,5,5-tri Tylhexanoate, t-butylperoxylaurate, t-butylperoxyisopropyl monocarbonate, t-butylperoxy-2-ethylhexylmonocarbonate, t-butylperoxyacetate, t-butylperoxy-m-toluyl Benzoate, t-butylperoxybenzoate, bis (t-butylperoxy) isophthalate, 2,5-dimethyl-2,5-bis (m-toluylperoxy) hexane, t-hexylperoxybenzoate, 2,5 -Dimethyl-2,5-bis (benzoylperoxy) hexane, t-butylperoxyallyl monocarbonate, t-butyltrimethylsilyl peroxide, 2,2-bis (4,4-di-t-butylperoxycyclohexyl) Propane, 3,3 ', 4,4'-teto La (t-butylperoxycarbonyl) benzophenone, t-amylperoxyisonanoate, t-amylperoxy-2-ethylhexanoate, sodium persulfate, potassium persulfate, ammonium persulfate, hydrogen peroxide, and other peroxides. Oxide-based initiator; 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 1-[(1-cyano-1-methylethyl) azo] formamide, 1,1′-azobis (cyclohexane-1-) Carbonitrile), 2,2'-azobis (2-methylbutyronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2 '-Azobis (2,4-dimethyl-4-methoxyvaleronitrile), 2,2'-azobis (2-methylpropionamidine) dihydride Chloride, 2,2′-azobis (2-methyl-N-phenylpropionamidine) dihydrochloride, 2,2′-azobis [N- (4-chlorophenyl) -2-methylpropionamidine] dihydrochloride, 2,2 ′ -Azobis [N- (4-hydrophenyl) -2-methylpropionamidine] dihydrochloride, 2,2'-azobis [2-methyl-N- (phenylmethyl) propionamidine] dihydrochloride, 2,2'-azobis [2-Methyl-N- (2-propenyl) propionamidine] dihydrochloride, 2,2′-azobis [N- (2-hydroxyethyl) -2-methylpropionamidine] dihydrochloride, 2,2′-azobis [ 2- (5-methyl-2-imidazolin-2-yl) propane] dihydrochloride, 2, '-Azobis [2- (2-imidazolin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (4,5,6,7-tetrahydro-1H-1,3-diazepine-2- Yl) propane] dihydrochloride, 2,2'-azobis [2- (3,4,5,6-tetrahydropyrimidin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (5-hydroxy) -3,4,5,6-Tetrahydropyrimidin-2-yl) propane] dihydrochloride, 2,2'-azobis {2- [1- (2-hydroxyethyl) -2-imidazolin-2-yl] propane} Dihydrochloride, 2,2'-azobis [2- (2-imidazolin-2-yl) propane], 2,2'-azobis {2-methyl-N- [1,1-bis (hydroxymethyl) ) -2-Hydroxyethyl] propionamide}, 2,2'-azobis {2-methyl-N- [1,1-bis (hydroxymethyl) ethyl] propionamide}, 2,2'-azobis [2-methyl -N- (2-hydroxyethyl) propionamide], 2,2'-azobis (2-methylpropionamide), 2,2'-azobis (2,4,4-trimethylpentane), 2,2'-azobis (2-methylpropane), dimethyl-2,2-azobis (2-methylpropionate), 4,4'-azobis (4-cyanopentanoic acid), 2,2'-azobis [2- (hydroxymethyl) Examples include azo initiators such as propionitrile] and 2,3-dimethyl-2,3-diphenylbutane.
上記熱ラジカル重合開始剤とともに使用できる熱ラジカル重合促進剤としては、コバルト、銅、錫、亜鉛、マンガン、鉄、ジルコニウム、クロム、バナジウム、カルシウム、カリウム等の金属石鹸;1級、2級、3級のアミン化合物;4級アンモニウム塩;チオ尿素化合物;ケトン化合物等が挙げられ、具体的には、例えば、オクチル酸コバルト、ナフテン酸コバルト、オクチル酸銅、ナフテン酸銅、オクチル酸マンガン、ナフテン酸マンガン、ジメチルアニリン、トリエタノールアミン、トリエチルベンジルアンモニウムクロライド、ジ(2−ヒドロキシエチル)p−トルイジン、エチレンチオ尿素、アセチルアセトン、アセト酢酸メチル等が挙げられる。 Examples of the thermal radical polymerization accelerator that can be used together with the thermal radical polymerization initiator include metal soaps such as cobalt, copper, tin, zinc, manganese, iron, zirconium, chromium, vanadium, calcium and potassium; primary, secondary, and tertiary. Amine compounds; quaternary ammonium salts; thiourea compounds; ketone compounds and the like. Specific examples include cobalt octylate, cobalt naphthenate, copper octylate, copper naphthenate, manganese octylate, and naphthenic acid. Examples thereof include manganese, dimethylaniline, triethanolamine, triethylbenzylammonium chloride, di (2-hydroxyethyl) p-toluidine, ethylenethiourea, acetylacetone and methyl acetoacetate.
上記光ラジカル重合開始剤としては、具体的には、例えば、2,2−ジエトキシアセトフェノン、2,2−ジメトキシー2−フェニルアセトフェノン、1−ヒドロキシシクロヘキシルフェニルケトン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、1−〔4−(2−ヒドロキシエトキシ)フェニル〕−2−ヒドロキシー2−メチル−1−プロパン−1−オン、2−ヒドロキシ−1−{4−〔4−(2−ヒドロキシ−2−メチルプロピオニル)ベンジル〕フェニル}−2−メチルプロパン−1−オン、2−メチル−1−(4−メチルチオフェニル)−2−モルフォリノプロパン1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1、2−(ジメチルアミノ)−2−〔(4−メチルフェニル)メチル〕−1−〔4−(4−モルホリニル)フェニル〕−1−ブタノン等のアルキルフェノン系化合物;ベンゾフェノン、4,4’−ビス(ジメチルアミノ)ベンゾフェノン、2−カルボキシベンゾフェノン等のベンゾフェノン系化合物;ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテ等のベンゾイン系化合物;チオキサントン、2−エチルチオキサントン、2−イソプロピルチオキサントン、2−クロロチオキサントン、2,4−ジメチルチオキサントン、2,4−ジエチルチオキサントン等のチオキサントン系化合物;2−(4−メトキシフェニル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−メトキシナフチル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−エトキシナフチル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−エトキシカルボキニルナフチル)−4,6−ビス(トリクロロメチル)−s−トリアジン等のハロメチル化トリアジン系化合物;2−トリクロロメチル−5−(2’−ベンゾフリル)−1,3,4−オキサジアゾール、2−トリクロロメチル−5−〔β−(2’−ベンゾフリル)ビニル〕−1,3,4−オキサジアゾール、4−オキサジアゾール、2−トリクロロメチル−5−フリル−1,3,4−オキサジアゾール等のハロメチル化オキサジアゾール系化合物;2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラフェニル−1,2’−ビイミダゾール、2,2’−ビス(2,4−ジクロロフェニル)−4,4’,5,5’−テトラフェニル−1,2’−ビイミダゾール、2,2’−ビス(2,4,6−トリクロロフェニル)−4,4’,5,5’−テトラフェニル−1,2’−ビイミダゾール等のビイミダゾール系化合物;1,2−オクタンジオン,1−〔4−(フェニルチオ)−,2−(O−ベンゾイルオキシム)〕、エタノン,1−〔9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル〕−,1−(O−アセチルオキシム)等のオキシムエステル系化合物;ビス(η5−2,4−シクロペンタジエン−1−イル)−ビス(2,6−ジフルオロ−3−(1H−ピロール−1−イル)−フェニル)チタニウム等のチタノセン系化合物;p−ジメチルアミノ安息香酸、p−ジエチルアミノ安息香酸等の安息香酸エステル系化合物;9−フェニルアクリジン等のアクリジン系化合物;等を挙げることができる。 Specific examples of the photoradical polymerization initiator include 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexylphenyl ketone, and 2-hydroxy-2-methyl-1. -Phenylpropan-1-one, 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1- {4- [4- ( 2-Hydroxy-2-methylpropionyl) benzyl] phenyl} -2-methylpropan-1-one, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2 -Dimethylamino-1- (4-morpholinophenyl) -butanone-1,2- (dimethylamino) -2-[(4-methyl Phenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone and other alkylphenone compounds; benzophenone, 4,4′-bis (dimethylamino) benzophenone, 2-carboxybenzophenone and other benzophenone compounds Compounds; benzoin-based compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutylate; thioxanthone, 2-ethylthioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4 A thioxanthone compound such as diethylthioxanthone; 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphthyl) -4,6 Bis (trichloromethyl) -s-triazine, 2- (4-ethoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-ethoxycarboquinylnaphthyl) -4,6-bis ( Halomethylated triazine compounds such as trichloromethyl) -s-triazine; 2-trichloromethyl-5- (2'-benzofuryl) -1,3,4-oxadiazole, 2-trichloromethyl-5- [β- ( 2'-benzofuryl) vinyl] -1,3,4-oxadiazole, 4-oxadiazole, 2-trichloromethyl-5-furyl-1,3,4-oxadiazole and other halomethylated oxadiazoles Compounds: 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2 4-dichlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4,4', 5 Biimidazole compounds such as 5'-tetraphenyl-1,2'-biimidazole; 1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)], ethanone, 1 Oxime ester compounds such as-[9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime); bis (η5-2,4-cyclopentadiene) -1-yl) -bis (2,6-difluoro-3- (1H-pyrrol-1-yl) -phenyl) titanium and other titanocene compounds; p-dimethylaminobenzoic acid, p-diethylaminoammonium Benzoic acid-based compounds such as benzoic acid; acridine-based compounds such as 9-phenylacridine; and the like.
上記単量体成分をラジカル重合機構により重合する場合、必要に応じて、公知の連鎖移動剤を使用してもよく、ラジカル重合開始剤と併用するのがより好ましい。このような連鎖移動剤としては、具体的には、例えば、メルカプト酢酸、3−メルカプトプロピオン酸等のメルカプトカルボン酸類;メルカプト酢酸メチル、3−メルカプトプロピオン酸メチル、3−メルカプトプロピオン酸2−エチルヘキシル、3−メルカプトプロピオン酸n−オクチル、3−メルカプトプロピオン酸メトキシブチル、3−メルカプトプロピオン酸ステアリル、トリメチロールプロパントリス(3−メルカプトプロピオネート)、ペンタエリスリトールテトラキス(3−メルカプトプロピオネート)、ジペンタエリスリトールヘキサキス(3−メルカプトプロピオネート)等のメルカプトカルボン酸エステル類;エチルメルカプタン、t−ブチルメルカプタン、n−ドデシルメルカプタン、1,2−ジメルカプトエタン等のアルキルメルカプタン類;2−メルカプトエタノール、4−メルカプト−1−ブタノール等のメルカプトアルコール類;ベンゼンチオール、m−トルエンチオール、p−トルエンチオール、2−ナフタレンチオール等の芳香族メルカプタン類;トリス〔(3−メルカプトプロピオニロキシ)−エチル〕イソシアヌレート等のメルカプトイソシアヌレート類;2−ヒドロキシエチルジスルフィド、テトラエチルチウラムジスルフィド等のジスルフィド類;ベンジルジエチルジチオカルバメート等のジチオカルバメート類;α−メチルスチレンダイマー等の単量体ダイマー類;四臭化炭素等のハロゲン化アルキル類などが挙げられる。これらの中では、入手性、架橋防止能、重合速度低下の度合いが小さいなどの点で、メルカプトカルボン酸類、メルカプトカルボン酸エステル類、アルキルメルカプタン類、メルカプトアルコール類、芳香族メルカプタン類;メルカプトイソシアヌレート類などのメルカプト基を有する化合物が好ましい。これらは単独で用いても、2種以上を併用してもよい。 When the above-mentioned monomer component is polymerized by a radical polymerization mechanism, a known chain transfer agent may be used if necessary, and it is more preferably used in combination with a radical polymerization initiator. Specific examples of such chain transfer agents include mercaptoacetic acid and mercaptocarboxylic acids such as 3-mercaptopropionic acid; methyl mercaptoacetate, methyl 3-mercaptopropionate, and 2-ethylhexyl 3-mercaptopropionate. 3-Mercaptopropionate n-octyl, 3-mercaptopropionate methoxybutyl, 3-mercaptopropionate stearyl, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), di- Mercaptocarboxylic acid esters such as pentaerythritol hexakis (3-mercaptopropionate); ethyl mercaptan, t-butyl mercaptan, n-dodecyl mercaptan, 1,2-dimercaptoethane, etc. Alkyl mercaptans; 2-mercaptoethanol, 4-mercapto-1-butanol and other mercapto alcohols; benzenethiol, m-toluenethiol, p-toluenethiol, 2-naphthalenethiol and other aromatic mercaptans; Tris [(3 -Mercaptopropionyloxy) -ethyl] isocyanurate and other mercaptoisocyanurates; 2-hydroxyethyl disulfide, tetraethyl thiuram disulfide and other disulfides; benzyldiethyldithiocarbamate and other dithiocarbamates; α-methylstyrene dimer and other single monomers Dimer dimers; alkyl halides such as carbon tetrabromide and the like. Among these, mercaptocarboxylic acids, mercaptocarboxylic acid esters, alkyl mercaptans, mercaptoalcohols, aromatic mercaptans; mercaptoisocyanurates, in terms of availability, crosslinking prevention ability, and low degree of polymerization rate decrease. A compound having a mercapto group such as a class is preferable. These may be used alone or in combination of two or more.
上記単量体成分をラジカル重合機構により重合する場合、3官能以上の多価メルカプタンおよび/または3官能以上の多官能開始剤の存在下にてラジカル重合を行っても良い。 When the above monomer component is polymerized by a radical polymerization mechanism, the radical polymerization may be performed in the presence of a trifunctional or higher polyvalent mercaptan and / or a trifunctional or higher polyfunctional initiator.
3官能以上の多価メルカプタンとしては、例えば、トリメチロールプロパントリメルカプトアセテート、トリメチロールプロパントリ(3−メルカプトプロピオネート)、ペンタエリスリトールテトラキスメルカプトアセテート、ペンタエリスリトールテトラキス(3−メルカプトプロピオネート)、ジペンタエリスリトールヘキサキスメルカプトアセテート、ジペンタエリスリトールヘキサキス(3−メルカプトプロピオネート)など、水酸基を3個以上有する化合物とカルボキシル基含有メルカプタン類のポリエステル化合物、トリアジン多価チオール類、多価エポキシ化合物の複数のエポキシ基に硫化水素を付加させて1分子当たり3個以上のメルカプト基を導入してなる化合物、多価カルボン酸の複数のカルボキシル基とメルカプトエタノールをエステル化してなる1分子当たり3個以上のメルカプト基を有する化合物などが挙げることができる。3官能以上の多価メルカプタンは、1種類以上を単独または組み合わせて(例えば、混合して)使用することができる。 Examples of the trifunctional or higher polyvalent mercaptan include, for example, trimethylolpropane trimercaptoacetate, trimethylolpropane tri (3-mercaptopropionate), pentaerythritol tetrakismercaptoacetate, pentaerythritol tetrakis (3-mercaptopropionate), Compounds having three or more hydroxyl groups and carboxyl group-containing mercaptan polyester compounds such as dipentaerythritol hexakismercaptoacetate and dipentaerythritol hexakis (3-mercaptopropionate), triazine polyvalent thiols, polyvalent epoxy compounds Hydrogen sulfide is added to a plurality of epoxy groups to introduce three or more mercapto groups per molecule, a plurality of carboxyl groups of a polycarboxylic acid and mercapto Ethanol to can be such compounds include having esterified three or more mercapto groups per molecule comprising. Trifunctional or higher polyvalent mercaptans can be used alone or in combination (for example, as a mixture).
上記3官能以上の多価メルカプタンの使用量(添加量総量)は、使用する単量体の種類や量、重合温度、重合濃度等の重合条件、目標とする重合体の分子量等に応じて適宜設定すればよく、特に限定されない。なお、基油溶解性が高い重量平均分子量が10万以上の重合体を含有する粘度指数向上剤を得る点から、3官能以上の多価メルカプタンの使用量は、単量体成分100質量部に対して、0.01質量部以上が好ましく、0.05質量部以上がより好ましく、また5質量部以下が好ましく、3質量部以下がより好ましく、2質量部以下がさらに好ましい。この範囲とすることで、分子量分布が狭くなり、せん断安定性を向上できる。 The amount of the trifunctional or higher polyvalent mercaptan used (total amount added) is appropriately determined depending on the type and amount of the monomers used, the polymerization conditions such as the polymerization temperature and the polymerization concentration, and the target molecular weight of the polymer. It may be set, and is not particularly limited. From the viewpoint of obtaining a viscosity index improver containing a polymer having a high base oil solubility and a weight average molecular weight of 100,000 or more, the amount of trifunctional or higher polyvalent mercaptan is 100 parts by mass of the monomer component. On the other hand, it is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, further preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and further preferably 2 parts by mass or less. Within this range, the molecular weight distribution can be narrowed and the shear stability can be improved.
3官能以上の多官能開始剤としては、例えば、2,2−ビス(4,4−t−ブチルパーオキシシクロヘキシル)プロパン、トリス(t−ブチルパーオキシ)トリアジン、3,3’,4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノンなどの3官能以上の有機過酸化物などが挙げられるが、特に限定されない。 Examples of trifunctional or higher polyfunctional initiators include 2,2-bis (4,4-t-butylperoxycyclohexyl) propane, tris (t-butylperoxy) triazine, 3,3 ', 4,4. Examples thereof include trifunctional or higher functional organic peroxides such as'-tetra (t-butylperoxycarbonyl) benzophenone, but are not particularly limited.
上記3官能以上の多官能開始剤の使用量(添加量総量)は、目的、用途に応じて適宜設定すればよく、特に限定されない。なお、重合性、分解物の悪影響、経済性のバランスを考慮し、さらに粘度指数と基油溶解性が高い重量平均分子量が10万以上の重合体を含有する粘度指数向上剤を得る点から、3官能以上の多官能開始剤の使用量は、単量体成分100質量部に対して、0.01質量部以上が好ましく、0.02質量部以上がより好ましく、0.05質量部以上がさらに好ましく、また10質量部以下が好ましく、5質量部以下がより好ましく、2質量部以下がさらに好ましい。 The amount of the trifunctional or more polyfunctional initiator used (total amount added) may be appropriately set depending on the purpose and application, and is not particularly limited. From the viewpoint of obtaining a viscosity index improver containing a polymer having a weight average molecular weight of 100,000 or more, which has a high viscosity index and a high base oil solubility, considering the balance between the polymerizability, the adverse effect of decomposed products, and the economic efficiency, The amount of the trifunctional or more polyfunctional initiator to be used is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, and 0.05 parts by mass or more with respect to 100 parts by mass of the monomer component. More preferably, 10 parts by mass or less, more preferably 5 parts by mass or less, still more preferably 2 parts by mass or less.
3官能以上の多価メルカプタンおよび/または3官能以上の多官能開始剤の存在下にて、単量体成分をラジカル重合することによって得られた重合体は、中心から高分子鎖が枝分かれした構造を有するものとなる。つまり、本発明の粘度指数向上剤に含まれる重合体は、3官能以上の多価メルカプタン由来の分岐単位および/または3官能以上の多官能開始剤由来の分岐単位を有するものとなる。粘度指数向上剤に含まれる重合体がこのような構造を有することにより、基油への溶解性を大きく損ねることなく、該重合体を含有する粘度指数向上剤のせん断安定性を改善することができる。 A polymer obtained by radically polymerizing a monomer component in the presence of a trifunctional or higher polyvalent mercaptan and / or a trifunctional or higher polyfunctional initiator has a structure in which a polymer chain is branched from the center. Will have. That is, the polymer contained in the viscosity index improver of the present invention has a trifunctional or higher functional polyvalent mercaptan-derived branch unit and / or a trifunctional or higher functional polyfunctional initiator-derived branch unit. Since the polymer contained in the viscosity index improver has such a structure, it is possible to improve the shear stability of the viscosity index improver containing the polymer without significantly impairing the solubility in the base oil. it can.
粘度指数向上剤に含まれる重合体が3官能以上の多価メルカプタン由来の分岐単位を有する場合、該重合体は、下記式(4)で示される分岐単位(連鎖移動剤残基)を有することが好ましい。下記式(4)において、LTはm価の有機残基を表し、mは0以上の数を表す。mは、好ましくは0〜5である。 When the polymer contained in the viscosity index improver has a trifunctional or higher functional polyvalent mercaptan-derived branching unit, the polymer should have a branching unit (chain transfer agent residue) represented by the following formula (4). Is preferred. In the following formula (4), L T represents an m-valent organic residue, and m represents a number of 0 or more. m is preferably 0-5.
粘度指数向上剤に含まれる重合体が3官能以上の多官能開始剤由来の分岐単位を有する場合、該重合体は、3官能以上の過酸化物由来の分岐単位を有することが好ましく、具体的には、下記式(5)で示される分岐単位を有することが好ましい。下記式(5)において、LSはn価の有機残基(開始剤残基)を表し、nは0以上の数を表す。nは、好ましくは0〜5である。 When the polymer contained in the viscosity index improver has a trifunctional or higher functional polyfunctional initiator-derived branching unit, the polymer preferably has a trifunctional or higher functional peroxide-derived branching unit. Preferably has a branching unit represented by the following formula (5). In the following formula (5), L S represents an n-valent organic residue (initiator residue), and n represents a number of 0 or more. n is preferably 0-5.
粘度指数向上剤に含まれる重合体は、3官能以上の多価メルカプタン由来の分岐単位と3官能以上の多官能開始剤由来の分岐単位のどちらか一方のみ含んでいてもよく、両方含んでいてもよい。3官能以上の多価メルカプタン由来の分岐単位は、1種のみ含まれていてもよく、2種以上含まれていてもよい。3官能以上の多官能開始剤由来の分岐単位も、1種のみ含まれていてもよく、2種以上含まれていてもよい。 The polymer contained in the viscosity index improver may contain only one of a trifunctional or higher functional polyvalent mercaptan-derived branch unit and a trifunctional or higher functional polyfunctional initiator-derived branch unit, or both of them. Good. The trifunctional or higher functional polyvalent mercaptan-derived branching unit may be contained alone or in combination of two or more. The branching unit derived from a trifunctional or higher polyfunctional initiator may be contained in only one kind or in two or more kinds.
重合体中の3官能以上の多価メルカプタン由来の分岐単位の含有量は、重合体100質量部に対し、0.01質量部以上が好ましく、0.05質量部以上がより好ましく、また5質量部以下が好ましく、3質量部以下がより好ましく、2質量部以下がさらに好ましい。この範囲とすることで、重合体の分子量分布が狭くなり、せん断安定性を向上できる。3官能以上の多価メルカプタン由来の分岐単位の含有量は、3官能以上の多価メルカプタンの使用量を重合体質量で除することにより求める。 The content of the trifunctional or higher polyvalent mercaptan-derived branch unit in the polymer is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, and 5 parts by mass with respect to 100 parts by mass of the polymer. The amount is preferably not more than 1 part, more preferably not more than 3 parts by mass, still more preferably not more than 2 parts by mass. Within this range, the molecular weight distribution of the polymer becomes narrow, and the shear stability can be improved. The content of the trifunctional or higher polyvalent mercaptan-derived branching unit is determined by dividing the amount of the trifunctional or higher polyvalent mercaptan used by the mass of the polymer.
重合体中の3官能以上の多官能開始剤由来の分岐単位の含有量は、粘度指数と基油溶解性が高い重量平均分子量が10万以上の重合体を含有する粘度指数向上剤を得る点から、重合体100質量部に対し、0.01質量部以上が好ましく、0.02質量部以上がより好ましく、0.05質量部以上がさらに好ましく、また10質量部以下が好ましく、5質量部以下がより好ましく、2質量部以下がさらに好ましい。3官能以上の多官能開始剤由来の分岐単位の含有量は、3官能以上の多官能開始剤の使用量を重合体質量で除することにより求める。 The content of branching units derived from a trifunctional or higher-functional polyfunctional initiator in the polymer is a point of obtaining a viscosity index improver containing a polymer having a high viscosity index and base oil solubility and a weight average molecular weight of 100,000 or more. Therefore, with respect to 100 parts by mass of the polymer, 0.01 parts by mass or more is preferable, 0.02 parts by mass or more is more preferable, 0.05 parts by mass or more is further preferable, and 10 parts by mass or less is preferable, and 5 parts by mass is preferable. The following is more preferable, and 2 parts by mass or less is further preferable. The content of the trifunctional or higher polyfunctional initiator-derived branching unit is determined by dividing the amount of the trifunctional or higher polyfunctional initiator used by the mass of the polymer.
本発明の粘度指数向上剤に含有される重合体の重合方法は、単量体成分を重合する工程(重合工程)を有する製造方法により得ることができる。重合工程における単量体の成分の重合方法は、たとえば、バルク重合、溶液重合、懸濁重合、乳化重合などいずれでもよいが、特に限定はされない。分散媒、乳化剤、分散剤等を使用する場合は、特に制限がなく公知のものが使用できる。 The method for polymerizing the polymer contained in the viscosity index improver of the present invention can be obtained by a production method having a step of polymerizing a monomer component (polymerization step). The method of polymerizing the component of the monomer in the polymerization step may be, for example, bulk polymerization, solution polymerization, suspension polymerization or emulsion polymerization, but is not particularly limited. When a dispersion medium, an emulsifier, a dispersant, etc. are used, known ones can be used without particular limitation.
重合工程で3官能以上の多価メルカプタンおよび/または3官能以上の多官能開始剤を用いる場合、それらの種類や使用量等の好適条件は、上記に説明した通りである。重合の際、3官能以上の多価メルカプタンおよび/または3官能以上の多官能開始剤は、一括添加してもよく、分割添加してもよい。また、2官能以下のメルカプタンや2官能以下の開始剤を併用してもよい。 When a trifunctional or higher polyvalent mercaptan and / or a trifunctional or higher functional polyfunctional initiator is used in the polymerization step, suitable conditions such as the type and the amount used are as described above. During the polymerization, the trifunctional or higher polyvalent mercaptan and / or the trifunctional or higher polyfunctional initiator may be added all at once or in divided portions. Further, a bifunctional or lower mercaptan or a bifunctional or lower initiator may be used in combination.
重合工程では、単量体成分として、上記に説明した一般式(1)で示される(a)単位を構成するための成分、(b)単位を構成するための一般式(2)で表されるアルキル(メタ)アクリレート成分、(c)単位を構成するための一般式(3)で表されるアルキル(メタ)アクリレート成分を必須的に用いることが好ましい。単量体成分として、上記に説明した(d)単位を構成するための成分を併用してもよい。これらの各単量体成分の種類や使用量等の好適条件は、上記に説明した通りである。 In the polymerization step, as a monomer component, a component for constituting the (a) unit represented by the above-described general formula (1) and a general formula (2) for constituting the (b) unit are represented. It is preferable to essentially use the alkyl (meth) acrylate component represented by the general formula (3) for constituting the unit (c). As the monomer component, the component for constituting the unit (d) described above may be used together. Suitable conditions such as the type and amount of each of these monomer components are as described above.
重合に使用する溶媒としては、重合反応に不活性なものであれば特に限定されるものではなく、重合機構、使用する単量体の種類や量、重合開始剤・重合触媒の種類や量等の重合条件に応じて適宜設定すればよい。なお、重合体の溶解度を確保する観点、および重合後に基油への溶媒置換が容易である観点から、重合に使用する溶媒としては、トルエン、キシレン、ヘキサン、シクロヘキサン、メチルエチルケトン、テトラヒドロフラン、酢酸エチル、酢酸ブチルが好ましい。また、後述する潤滑油基油も溶媒として好適に用いることができる。この場合、重合後の溶媒置換が不要となり、プロセスが簡略化されるため、より好ましい。これら溶媒は単独で用いても、2種以上を併用してもよい。溶媒の使用量は特に制限はないが、粘度指数が高い重量平均分子量が10万以上の重合体を得る観点から、単量体成分、重合開始剤、その他の成分の合計量の濃度が、全体の20質量%以上80質量%以下となる程度が好ましい。 The solvent used for the polymerization is not particularly limited as long as it is inert to the polymerization reaction, the polymerization mechanism, the type and amount of the monomer used, the type and amount of the polymerization initiator and the polymerization catalyst, etc. It may be appropriately set according to the polymerization conditions of. Incidentally, from the viewpoint of ensuring the solubility of the polymer, and from the viewpoint of easy solvent substitution to the base oil after the polymerization, as the solvent used for the polymerization, toluene, xylene, hexane, cyclohexane, methyl ethyl ketone, tetrahydrofuran, ethyl acetate, Butyl acetate is preferred. Further, the lubricating base oil described below can also be suitably used as the solvent. In this case, solvent replacement after the polymerization is not necessary and the process is simplified, which is more preferable. These solvents may be used alone or in combination of two or more. The amount of the solvent used is not particularly limited, but from the viewpoint of obtaining a polymer having a high viscosity index and a weight average molecular weight of 100,000 or more, the total concentration of the monomer component, the polymerization initiator and the other components is 20 mass% or more and 80 mass% or less is preferable.
上記単量体成分を重合する際の重合温度としては、重合機構、使用する単量体の種類や量、重合開始剤・重合触媒の種類や量等に応じて適宜設定すればよく、特に限定されないが、0℃以上が好ましく、25℃以上がより好ましく、また200℃以下が好ましく、150℃以下がより好ましい。重合温度が0℃未満であると、重合反応が非常に遅くなり、200℃を超えると反応が激しく制御が困難となるため、いずれも好ましくない。 The polymerization temperature at the time of polymerizing the monomer component may be appropriately set depending on the polymerization mechanism, the type and amount of the monomer used, the type and amount of the polymerization initiator / polymerization catalyst, and is not particularly limited. However, the temperature is preferably 0 ° C. or higher, more preferably 25 ° C. or higher, preferably 200 ° C. or lower, and more preferably 150 ° C. or lower. If the polymerization temperature is lower than 0 ° C., the polymerization reaction becomes very slow, and if it exceeds 200 ° C., the reaction becomes violent and difficult to control.
本発明の粘度指数向上剤に含まれる重合体は、重量平均分子量(Mw)が2万以上であり、10万以上であることが好ましく、20万以上がより好ましく、25万以上がさらに好ましく、30万以上がさらにより好ましく、また50万未満であり、49万以下が好ましく、48万以下がより好ましい。重合体の重量平均分子量が上記下限値に満たない場合は、潤滑油組成物の粘度指数が低くなるだけでなく、所望の粘度に調整するために粘度指数向上剤の使用量を増やす必要があり、コスト面で不利となる。重合体の重量平均分子量が過度に大きい場合は、粘度指数向上剤の基油への溶解性が不足したり潤滑油組成物のせん断安定性が低下したりする傾向がある。 The polymer contained in the viscosity index improver of the present invention has a weight average molecular weight (Mw) of 20,000 or more, preferably 100,000 or more, more preferably 200,000 or more, further preferably 250,000 or more, It is more preferably 300,000 or more, less than 500,000, preferably 490,000 or less, and more preferably 480,000 or less. When the weight average molecular weight of the polymer is less than the above lower limit value, not only the viscosity index of the lubricating oil composition becomes low, but also it is necessary to increase the amount of the viscosity index improver used to adjust the viscosity to a desired value. However, it is disadvantageous in terms of cost. If the weight average molecular weight of the polymer is excessively large, the solubility of the viscosity index improver in the base oil tends to be insufficient, and the shear stability of the lubricating oil composition tends to decrease.
本発明の粘度指数向上剤に含まれる重合体の数平均分子量(Mn)は0.8万以上が好ましく、9万以上が好ましく、より好ましくは9万〜22万であり、さらに好ましくは9万〜20万である。 The number average molecular weight (Mn) of the polymer contained in the viscosity index improver of the present invention is preferably 80,000 or more, preferably 90,000 or more, more preferably 90,000 to 220,000, and further preferably 90,000. ~ 200,000.
MwとMnから算出される分子量分布(Mw/Mn)は4.0以下が好ましく、より好ましくは3.5以下であり、さらに好ましくは3.0以下である。分子量分布が4.0を超えると粘度指数向上剤の基油への溶解性が不足したり、潤滑油組成物のせん断安定性が低下したりするため好ましくない。一方、分子量分布の下限は1.0が好ましいが、重合体の合成が容易な点から、分子量分布(Mw/Mn)は1.5以上が好ましく、2.0以上がより好ましく、2.3以上がさらに好ましい。なお、本発明におけるMwおよびMnは、公知の方法を用いて測定することができる。 The molecular weight distribution (Mw / Mn) calculated from Mw and Mn is preferably 4.0 or less, more preferably 3.5 or less, and further preferably 3.0 or less. If the molecular weight distribution exceeds 4.0, the solubility of the viscosity index improver in the base oil becomes insufficient, and the shear stability of the lubricating oil composition decreases, which is not preferable. On the other hand, the lower limit of the molecular weight distribution is preferably 1.0, but from the viewpoint of easy synthesis of the polymer, the molecular weight distribution (Mw / Mn) is preferably 1.5 or more, more preferably 2.0 or more, and 2.3. The above is more preferable. In addition, Mw and Mn in this invention can be measured using a well-known method.
分子量の制御方法としては、公知の方法を用いることができる。例えば、重合開始剤・重合触媒の量や種類、重合温度、連鎖移動剤の種類や量の調整などにより制御できる。分子量分布を制御する方法としてはLiving Radical Polymerizationも使用できる。具体的な方法としては、RAFT法やNMP法、ATRP法などが有名である。詳細については、Aldrich Material Matters,Vol.5,No.1,2010に概説されている。使用例としては、例えばRAFT法の場合、特開2012−197399号公報において、重合開始剤として2,2’−アゾビスイソブチロニトリル、重合触媒として、ジチオ安息香酸クミルが用いられている。 A known method can be used as a method for controlling the molecular weight. For example, it can be controlled by adjusting the amount and type of the polymerization initiator / polymerization catalyst, the polymerization temperature, and the type and amount of the chain transfer agent. Living Radical Polymerization can also be used as a method for controlling the molecular weight distribution. RAFT method, NMP method, ATRP method and the like are famous as specific methods. For details, see Aldrich Material Matters, Vol. 5, No. 1, 2010. As an example of use, in the case of RAFT method, in JP 2012-197399 A, 2,2'-azobisisobutyronitrile is used as a polymerization initiator and cumyl dithiobenzoate is used as a polymerization catalyst.
本発明の粘度指数向上剤に含まれる重合体の分岐度は1.0以上が好ましく、より好ましくは1.4以上であり、また10.0以下が好ましく、6.0以下がより好ましく、4.0以下がさらに好ましい。分岐度が1.0よりも小さい場合には、重合体の分岐構造が十分ではなく、せん断安定性の改善が期待できない。なお、本発明における分岐度は、重合体1分子あたりの分岐点の数の平均に相当し、論理的には、例えば、分岐のない直鎖の重合体の分岐度は0となり、唯一の分岐点から3本のポリマー鎖が伸びている重合体の分岐度は1となり、4本のポリマー鎖が伸びている重合体の分岐度は2となり、5本のポリマー鎖が伸びている重合体の分岐度は3となる。 The degree of branching of the polymer contained in the viscosity index improver of the present invention is preferably 1.0 or more, more preferably 1.4 or more, and preferably 10.0 or less, more preferably 6.0 or less, 4 It is more preferably 0.0 or less. When the branching degree is less than 1.0, the branched structure of the polymer is not sufficient and improvement in shear stability cannot be expected. The branching degree in the present invention corresponds to the average of the number of branching points per polymer molecule, and theoretically, for example, a straight-chain polymer having no branching has a branching degree of 0, and the only branching point is The degree of branching of a polymer in which three polymer chains extend from the point is 1, and the degree of branching of a polymer in which four polymer chains extend is 2 and that of a polymer in which five polymer chains extend. The degree of branching is 3.
上述した重合体の粘度指数向上剤中の含有量は、本発明の効果を損なわない範囲である限り特に限定されないが、本発明の粘度指数向上剤は上述した重合体を主成分として含むことが好ましい。粘度指数向上剤中の重合体の含有量は、粘度指数向上剤100質量部に対して、例えば50質量部以上が好ましく、80質量部以上がより好ましく、90質量部以上がさらに好ましい。 The content of the above-mentioned polymer in the viscosity index improver is not particularly limited as long as the effect of the present invention is not impaired, but the viscosity index improver of the present invention may contain the above-mentioned polymer as a main component. preferable. The content of the polymer in the viscosity index improver is, for example, preferably 50 parts by mass or more, more preferably 80 parts by mass or more, still more preferably 90 parts by mass or more, relative to 100 parts by mass of the viscosity index improver.
本発明の粘度指数向上剤に含まれる重合体のSP値(溶解度パラメーター)は、8.8以上が好ましく、8.9以上がより好ましく、9.0以上がさらに好ましく、また9.6以下が好ましく、9.5以下がより好ましく、9.4以下がさらに好ましい。基油のSP値は一般に8.0〜8.5程度の値を示すが、重合体のSP値が8.8以上であれば潤滑油組成物の粘度指数を高めやすくなり、重合体のSP値が9.6以下であれば粘度指数向上剤の基油への溶解性を確保しやすくなる。SP値は、公知の方法を用いて求めることができる。 The SP value (solubility parameter) of the polymer contained in the viscosity index improver of the present invention is preferably 8.8 or more, more preferably 8.9 or more, further preferably 9.0 or more, and 9.6 or less. It is preferably 9.5 or less, more preferably 9.4 or less. The SP value of the base oil generally indicates a value of about 8.0 to 8.5, but if the SP value of the polymer is 8.8 or more, the viscosity index of the lubricating oil composition is easily increased, and the SP value of the polymer is increased. When the value is 9.6 or less, it becomes easy to secure the solubility of the viscosity index improver in the base oil. The SP value can be obtained using a known method.
本発明の粘度指数向上剤は、粘度指数向上効果とせん断安定性を高いレベルで両立できる。せん断安定性の具体的数値としては、例えば、PSSI(パーマネントシアスタビリティインデックス:ASTM D 6022)や下記に示す方法で求めるSSI、または分解開始温度が指標となる。
本発明におけるSSIは、後述の実施例に記載の方法にて測定した値である。すなわち、100℃における動粘度が7.0mm2/秒となるように、基油(SK製:YUBASE4)に重合体を希釈し、以下の条件で超音波を照射した。
装置:Hielscher Ultrasonics社製 UP400S
設定:Amplitude=70%、Cycle=1
時間:10分
温度:100℃
せん断前後および基油の100℃における動粘度を測定し、SSI={1−(せん断後の動粘度−基油の動粘度)/(せん断前の動粘度−基油の動粘度)}×100の式で計算した。
The viscosity index improver of the present invention can achieve both a high viscosity index improving effect and a high shear stability. As a specific numerical value of the shear stability, for example, PSSI (Permanent Shear Stability Index: ASTM D 6022), SSI obtained by the method shown below, or decomposition start temperature is used as an index.
The SSI in the present invention is a value measured by the method described in Examples below. That is, the polymer was diluted in base oil (YUBASE4 manufactured by SK) so that the kinematic viscosity at 100 ° C. was 7.0 mm 2 / sec, and ultrasonic waves were irradiated under the following conditions.
Device: Hielscher Ultrasonics UP400S
Settings: Amplitude = 70%, Cycle = 1
Time: 10 minutes Temperature: 100 ° C
The kinematic viscosities of the base oil before and after shearing and at 100 ° C. were measured, and SSI = {1- (kinematic viscosity after shearing−kinematic viscosity of base oil) / (kinematic viscosity before shearing−kinematic viscosity of base oil)} × 100 It calculated by the formula.
本発明において、せん断安定性の指標とする粘度指数向上剤のSSIは、45以下であることが好ましく、より好ましくは40以下であり、さらに好ましくは38以下である。また、前記SSIは、0.1以上であることが好ましく、より好ましくは0.5以上であり、さらに好ましくは2以上であり、特に好ましくは5以上である。SSIが0.1未満の場合には粘度指数向上効果が小さくコストが上昇するおそれがあり、SSIが45を超える場合にはせん断安定性や貯蔵安定性が悪くなるおそれがある。 In the present invention, the SSI of the viscosity index improver, which is an index of shear stability, is preferably 45 or less, more preferably 40 or less, and further preferably 38 or less. Further, the SSI is preferably 0.1 or more, more preferably 0.5 or more, further preferably 2 or more, and particularly preferably 5 or more. If the SSI is less than 0.1, the effect of improving the viscosity index may be small and the cost may increase, and if the SSI is more than 45, the shear stability and storage stability may be deteriorated.
粘度指数向上剤の分解開始温度は、290℃以上であることが好ましく、295℃以上がより好ましく、300℃以上がさらに好ましく、310℃以上が特に好ましく、また500℃以下が好ましく、450℃以下がより好ましく、400℃以下がさらに好ましく、380℃以下が特に好ましい。粘度指数向上剤の分解開始温度が高くなることにより、耐熱性が向上し、熱分解安定性、せん断安定性が良好なものとなる。一方で過度に耐熱性を向上させた場合は、基油への溶解性が不足したり粘度指数が低下したりする傾向がある。 The decomposition initiation temperature of the viscosity index improver is preferably 290 ° C or higher, more preferably 295 ° C or higher, further preferably 300 ° C or higher, particularly preferably 310 ° C or higher, and preferably 500 ° C or lower, 450 ° C or lower. Is more preferable, 400 ° C. or lower is further preferable, and 380 ° C. or lower is particularly preferable. By increasing the decomposition start temperature of the viscosity index improver, heat resistance is improved, and thermal decomposition stability and shear stability are improved. On the other hand, when the heat resistance is excessively improved, the solubility in the base oil tends to be insufficient and the viscosity index tends to decrease.
本発明の粘度指数向上剤は、上述した重合体を主成分として含み、好ましくは粘度指数向上剤100質量%中、重合体を70質量%以上、より好ましくは90質量%以上、さらに好ましくは95質量%以上、特に好ましくは99質量%以上、100質量%以下含有する。 The viscosity index improver of the present invention contains the above-mentioned polymer as a main component, and preferably 100% by mass or more of the polymer in 100% by mass of the viscosity index improver, more preferably 90% by mass or more, and further preferably 95%. It is contained in an amount of not less than mass%, particularly preferably not less than 99% and not more than 100% by mass.
〔2.粘度指数向上剤と基油を含有する組成物〕
本発明は、本発明の粘度指数向上剤を含有する潤滑油組成物も提供する。本発明の粘度指数向上剤は、潤滑油基油と配合して、潤滑油組成物とすることができる。潤滑油組成物は、それをさらに潤滑油基油で希釈せずに潤滑油に用いてもよく、あるいは、さらに潤滑油基油で希釈したものを潤滑油に用いてもよい。後者の場合、潤滑油組成物は原液として用いられ、以下これを「基油組成物」と称する場合がある。
[2. Composition containing viscosity index improver and base oil]
The present invention also provides a lubricating oil composition containing the viscosity index improver of the present invention. The viscosity index improver of the present invention can be blended with a lubricating base oil to give a lubricating oil composition. The lubricating oil composition may be used as a lubricating oil without further diluting it with a lubricating base oil, or may be diluted with a lubricating base oil and used as a lubricating oil. In the latter case, the lubricating oil composition is used as a stock solution, which may hereinafter be referred to as the "base oil composition".
潤滑油基油としては、公知の潤滑油基油を特に制限なく用いることができ、鉱油系基油や合成系基油を好適に挙げることができる。鉱油系基油としては、パラフィン系やナフテン系等の基油が挙げられる。鉱物系基油には、原料基油を溶剤精製、水素化分解または水素化異性化処理したものも含まれる。合成系基油としては、炭化水素系、エステル系、エーテル系、シリコン系、フッ素系等の基油が挙げられる。潤滑油基油は、上述したように、粘度指数向上剤に含まれる重合体の重合反応溶媒として用いることもできる。 As the lubricant base oil, known lubricant base oils can be used without particular limitation, and mineral oil base oils and synthetic base oils can be preferably mentioned. Examples of the mineral oil-based base oil include paraffin-based and naphthene-based base oils. Mineral base oils also include those obtained by subjecting raw material base oils to solvent refining, hydrocracking or hydroisomerization. Examples of synthetic base oils include hydrocarbon-based, ester-based, ether-based, silicon-based, and fluorine-based base oils. The lubricating base oil can also be used as a polymerization reaction solvent for the polymer contained in the viscosity index improver, as described above.
鉱油系基油の好ましい具体例としては、以下に示す基油(1)〜(7)を原料とし、この原料油及び/又はこの原料油から回収された潤滑油留分を、所定の精製方法によって精製し、潤滑油留分を回収することによって得られる基油を挙げることができる。また(1)〜(7)から選ばれる基油又は当該基油から回収された潤滑油留分について所定の処理を行うことにより得られる下記基油(8)または(9)が特に好ましい。
(1)パラフィン基系原油および/または混合基系原油の常圧蒸留残渣油の減圧蒸留による留出油(WVGO)
(2)潤滑油脱ろう工程により得られるワックス(スラックワックス等)および/またはガストゥリキッド(GTL)プロセス等により得られる合成ワックス(フィッシャートロプシュワックス、GTLワックス等)
(3)基油(1)〜(2)から選ばれる1種または2種以上の混合油および/または当該混合油のマイルドハイドロクラッキング処理油
(4)基油(1)〜(3)から選ばれる2種以上の混合油
(5)基油(1)〜(4)のいずれかの脱れき油(DAO)
(6)基油(5)のマイルドハイドロクラッキング処理油(MHC)
(7)基油(1)〜(6)から選ばれる2種以上の混合油。
(8)上記基油(1)〜(7)から選ばれる基油又は当該基油から回収された潤滑油留分を水素化分解し、その生成物又はその生成物から蒸留等により回収される潤滑油留分について溶剤脱ろうや接触脱ろうなどの脱ろう処理を行い、又は当該脱ろう処理をした後に蒸留することによって得られる水素化分解鉱油。
(9)上記基油(1)〜(7)から選ばれる基油又は当該基油から回収された潤滑油留分を水素化異性化し、その生成物又はその生成物から蒸留等により回収される潤滑油留分について溶剤脱ろうや接触脱ろうなどの脱ろう処理を行い、又は、当該脱ろう処理をしたあとに蒸留することによって得られる水素化異性化鉱油。
As a preferred specific example of the mineral oil-based base oil, the base oils (1) to (7) shown below are used as raw materials, and the raw oil and / or the lubricating oil fraction recovered from the raw oil are subjected to a predetermined refining method. A base oil obtained by refining and recovering a lubricating oil fraction can be mentioned. Further, the following base oil (8) or (9) obtained by subjecting the base oil selected from (1) to (7) or the lubricating oil fraction recovered from the base oil to a predetermined treatment is particularly preferable.
(1) Normal pressure distillation of paraffin-based crude oil and / or mixed base crude oil Distillate oil (WVGO) obtained by vacuum distillation of residual oil
(2) Wax (slack wax, etc.) obtained by the dewaxing process of lubricating oil and / or synthetic wax (Fischer-Tropsch wax, GTL wax, etc.) obtained by gas to liquid (GTL) process, etc.
(3) One or two or more mixed oils selected from base oils (1) to (2) and / or mild hydrocracking treated oil (4) base oils (1) to (3) of the mixed oil. Two or more kinds of mixed oil (5) Base oil (1) to (4) any deasphalted oil (DAO)
(6) Base oil (5) mild hydrocracking treated oil (MHC)
(7) Two or more kinds of mixed oils selected from base oils (1) to (6).
(8) The base oil selected from the above base oils (1) to (7) or the lubricating oil fraction recovered from the base oil is hydrocracked, and the product or the product is recovered by distillation or the like. A hydrocracked mineral oil obtained by subjecting a lubricating oil fraction to dewaxing treatment such as solvent dewaxing or catalytic dewaxing, or distilling after the dewaxing treatment.
(9) The base oil selected from the above base oils (1) to (7) or the lubricating oil fraction recovered from the base oil is hydroisomerized, and the product or the product is recovered by distillation or the like. A hydroisomerized mineral oil obtained by subjecting a lubricating oil fraction to dewaxing treatment such as solvent dewaxing or catalytic dewaxing, or by subjecting it to distillation.
合成系基油としては、具体的には、ポリα−オレフィン又はその水素化物、イソブテンオリゴマー又はその水素化物、イソパラフィン、アルキルベンゼン、アルキルナフタレン、ジエステル(ジトリデシルグルタレート、ジ−2−エチルヘキシルアジペート、ジイソデシルアジペート、ジトリデシルアジペート、ジ−2−エチルヘキシルセバケート等)、ポリオールエステル(トリメチロールプロパンカプリレート、トリメチロールプロパンペラルゴネート、ペンタエリスリトール2−エチルヘキサノエート、ペンタエリスリトールペラルゴネート等)、ポリオキシアルキレングリコール、ジアルキルジフェニルエーテル、ポリフェニルエーテル等が挙げられ、なかでもポリα−オレフィンが好ましい。ポリα−オレフィンとしては、典型的には、炭素数2〜32、好ましくは6〜16のα−オレフィンのオリゴマー又はコオリゴマー(1−オクテンオリゴマー、デセンオリゴマー、エチレン−プロピレンコオリゴマー等)及びそれらの水素化物が挙げられる。合成系基油の100℃における動粘度は、1〜20mm2/秒であることが好ましい。 Specific examples of synthetic base oils include poly α-olefins or hydrides thereof, isobutene oligomers or hydrides thereof, isoparaffin, alkylbenzenes, alkylnaphthalenes, diesters (ditridecyl glutarate, di-2-ethylhexyl adipate, diisodecyl. Adipate, ditridecyl adipate, di-2-ethylhexyl sebacate, etc.), polyol ester (trimethylolpropane caprylate, trimethylolpropane pelargonate, pentaerythritol 2-ethylhexanoate, pentaerythritol pelargonate, etc.), polyoxyalkylene Examples thereof include glycol, dialkyldiphenyl ether, polyphenyl ether and the like, and among them, poly α-olefin is preferable. As the poly α-olefin, typically, an oligomer or cooligomer of an α-olefin having 2 to 32 carbon atoms, preferably 6 to 16 carbon atoms (1-octene oligomer, decene oligomer, ethylene-propylene cooligomer, etc.) and those The hydride of is mentioned. The kinematic viscosity of the synthetic base oil at 100 ° C. is preferably 1 to 20 mm 2 / sec.
潤滑油組成物に配合する潤滑油基油としては、上記基油(1)〜(7)から選ばれる基油又は当該基油から回収された潤滑油留分について、潤滑油組成物の粘度指数を高くする理由から上述の処理を行うことにより得られる基油(8)または(9)が特に好ましい。また、米国石油協会(API)による分類に基づくグループIIIに属する基油を用いることも好ましい。潤滑油組成物に配合する潤滑油基油としては、上述の合成系基油を用いてもよい。 The lubricating base oil to be blended in the lubricating oil composition is a base oil selected from the above base oils (1) to (7) or a lubricating oil fraction recovered from the base oil, and the viscosity index of the lubricating oil composition. The base oil (8) or (9) obtained by carrying out the above-mentioned treatment is particularly preferable for the reason of increasing the value. It is also preferable to use a base oil belonging to Group III based on classification by the American Petroleum Institute (API). As the lubricating base oil to be added to the lubricating oil composition, the above-mentioned synthetic base oil may be used.
本発明の潤滑油組成物においては、上記の潤滑油基油を単独で用いてもよく、また他の基油の1種又は2種以上と併用してもよい。なお、潤滑油基油と他の基油とを併用して混合基油とする場合、潤滑油組成物の粘度指数を高くする理由から当該混合基油は上記潤滑油基油(8)または(9)を少なくとも含むことが好ましい。混合基油中の上記潤滑油基油(8)または(9)の割合は、30質量%以上であることが好ましく、50質量%以上であることがより好ましく、70質量%以上であることがさらに好ましい。 In the lubricating oil composition of the present invention, the above-mentioned lubricating base oil may be used alone or in combination with one or more other base oils. When a lubricating base oil is used in combination with another base oil to form a mixed base oil, the mixed base oil is the above-mentioned lubricating base oil (8) or (for the reason of increasing the viscosity index of the lubricating oil composition. It is preferable to include at least 9). The proportion of the lubricating base oil (8) or (9) in the mixed base oil is preferably 30% by mass or more, more preferably 50% by mass or more, and 70% by mass or more. More preferable.
潤滑油基油の粘度指数は、100以上であることが好ましく、120以上がより好ましく、また160以下が好ましい。粘度指数が上記の下限値未満であると、粘度−温度特性及び熱・酸化安定性、揮発防止性が悪化するだけでなく、摩擦係数が上昇する傾向にあり、また、摩耗防止性が低下する傾向にある。また、粘度指数が上記の上限値を超えると、低温粘度特性が低下する傾向にある。なお、本発明でいう粘度指数とは、JIS K 2283に準拠して測定された粘度指数を意味する。 The viscosity index of the lubricating base oil is preferably 100 or more, more preferably 120 or more, and preferably 160 or less. When the viscosity index is less than the above lower limit value, not only the viscosity-temperature characteristics, heat / oxidation stability, and volatility preventive property deteriorate, but also the friction coefficient tends to increase, and the antiwear property decreases. There is a tendency. Further, when the viscosity index exceeds the above upper limit value, the low temperature viscosity characteristic tends to deteriorate. The viscosity index as referred to in the present invention means the viscosity index measured according to JIS K 2283.
潤滑油組成物の粘度指数は、200以上400以下であることが好ましく、230以上300以下であることがより好ましい。粘度指数が上記の範囲内であれば、省燃費性と熱・酸化安定性、貯蔵安定性に優れる。 The viscosity index of the lubricating oil composition is preferably 200 or more and 400 or less, and more preferably 230 or more and 300 or less. When the viscosity index is within the above range, fuel economy, heat / oxidation stability, and storage stability are excellent.
潤滑油組成物中の本発明の粘度指数向上剤の含有量は特に限定されず、例えば、潤滑油組成物の全量を基準として、0.01質量%以上が好ましく、0.1質量%以上がより好ましく、0.5質量%以上がさらに好ましく、また70質量%以下が好ましく、60質量%以下がより好ましく、50質量%未満がさらに好ましい。なお、潤滑油組成物をさらに潤滑油基油で希釈せずに潤滑油に用いる場合は、潤滑油組成物中の本発明の粘度指数向上剤の含有量は、潤滑油組成物の全量を基準として、0.01質量%以上が好ましく、0.1質量%以上がより好ましく、0.5質量%以上がさらに好ましく、また20質量%以下が好ましく、15質量%以下がより好ましく、10質量%以下がさらに好ましい。本発明の潤滑油組成物を基油組成物として用いる場合は、基油組成物中の本発明の粘度指数向上剤の含有量は、例えば5質量%以上が好ましく、10質量%以上がより好ましく、20質量%以上がさらに好ましく、また70質量%以下が好ましく、60質量%以下がより好ましく、50質量%未満がさらに好ましい。 The content of the viscosity index improver of the present invention in the lubricating oil composition is not particularly limited, and for example, 0.01% by mass or more is preferable and 0.1% by mass or more is based on the total amount of the lubricating oil composition. It is more preferably 0.5% by mass or more, further preferably 70% by mass or less, more preferably 60% by mass or less, and further preferably less than 50% by mass. When the lubricating oil composition is used as a lubricating oil without further diluting with a lubricating base oil, the content of the viscosity index improver of the present invention in the lubricating oil composition is based on the total amount of the lubricating oil composition. 0.01 mass% or more is preferable, 0.1 mass% or more is more preferable, 0.5 mass% or more is further preferable, 20 mass% or less is preferable, 15 mass% or less is more preferable, and 10 mass% is The following is more preferable. When the lubricating oil composition of the present invention is used as a base oil composition, the content of the viscosity index improver of the present invention in the base oil composition is, for example, preferably 5 mass% or more, more preferably 10 mass% or more. 20 mass% or more is more preferable, 70 mass% or less is preferable, 60 mass% or less is more preferable, and less than 50 mass% is further preferable.
本発明の潤滑油組成物は、本発明の粘度指数向上剤と潤滑油基油を必須成分として含有し、さらに任意の添加剤等を含有してもよい。潤滑油組成物は、例えば、流動点降下剤、摩耗防止剤、金属系清浄分散剤、無灰清浄分散剤、酸化防止剤、腐食防止剤、泡消剤及び摩擦調整剤よりなる群から選ばれる少なくとも1種の添加剤をさらに含有することが好ましい。 The lubricating oil composition of the present invention contains the viscosity index improver of the present invention and a lubricating base oil as essential components, and may further contain optional additives and the like. The lubricating oil composition is selected, for example, from the group consisting of pour point depressants, antiwear agents, metallic detergent dispersants, ashless detergent dispersants, antioxidants, corrosion inhibitors, defoamers and friction modifiers. It is preferable to further contain at least one additive.
流動点降下剤としては、潤滑油に用いられる任意の流動点降下剤が使用できる。流動点降下剤としては、例えば、ポリメタクリレート類、ナフタレン−塩素化パラフィン縮合生成物、フェノール−塩素化パラフィン縮合生成物などが挙げられる。これらの中ではポリメタクリレート類の添加が好ましい。 As the pour point depressant, any pour point depressant used for lubricating oil can be used. Examples of the pour point depressant include polymethacrylates, naphthalene-chlorinated paraffin condensation products, phenol-chlorinated paraffin condensation products, and the like. Among these, addition of polymethacrylates is preferable.
摩耗防止剤(又は極圧剤)としては、潤滑油に用いられる任意の摩耗防止剤・極圧剤が使用できる。摩耗防止剤(又は極圧剤)としては、例えば、硫黄系、リン系、硫黄−リン系の極圧剤等が使用でき、具体的には、ジアルキルジチオリン酸亜鉛(ZnDTP)、亜リン酸エステル類、チオ亜リン酸エステル類、ジチオ亜リン酸エステル類、トリチオ亜リン酸エステル類、リン酸エステル類、チオリン酸エステル類、ジチオリン酸エステル類、トリチオリン酸エステル類、これらのアミン塩、これらの金属塩、これらの誘導体、ジチオカーバメート、亜鉛ジチオカーバメート、MoDTC、ジサルファイド類、ポリサルファイド類、硫化オレフィン類、硫化油脂類等が挙げられる。これらの中では硫黄系極圧剤の添加が好ましく、特に硫化油脂が好ましい。 As the antiwear agent (or extreme pressure agent), any antiwear agent / extreme pressure agent used for lubricating oil can be used. As the antiwear agent (or extreme pressure agent), for example, a sulfur-based, phosphorus-based, sulfur-phosphorus-based extreme pressure agent, or the like can be used. Specifically, zinc dialkyldithiophosphate (ZnDTP), phosphite ester , Thiophosphites, dithiophosphites, trithiophosphites, phosphates, thiophosphates, dithiophosphates, trithiophosphates, amine salts thereof, these Examples thereof include metal salts, derivatives thereof, dithiocarbamates, zinc dithiocarbamates, MoDTC, disulfides, polysulfides, sulfurized olefins, sulfurized fats and oils. Among these, addition of a sulfur-based extreme pressure agent is preferable, and sulfurized fats and oils are particularly preferable.
金属系清浄分散剤としては、アルカリ金属/アルカリ土類金属スルホネート、アルカリ金属/アルカリ土類金属フェネート、及びアルカリ金属/アルカリ土類金属サリシレート等の正塩又は塩基性塩を挙げることができる。アルカリ金属としてはナトリウム、カリウム等、アルカリ土類金属としてはマグネシウム、カルシウム、バリウム等が挙げられるが、マグネシウム又はカルシウムが好ましく、特にカルシウムが好ましい。 Examples of the metal-based detergent-dispersant include normal salts or basic salts such as alkali metal / alkaline earth metal sulfonates, alkali metal / alkaline earth metal phenates, and alkali metal / alkaline earth metal salicylates. Examples of the alkali metal include sodium and potassium, and examples of the alkaline earth metal include magnesium, calcium and barium. Magnesium or calcium is preferable, and calcium is particularly preferable.
無灰清浄分散剤としては、潤滑油に用いられる任意の無灰清浄分散剤が使用できる。無灰清浄分散剤としては、例えば、炭素数40〜400の直鎖もしくは分枝状のアルキル基又はアルケニル基を分子中に少なくとも1個有するモノ又はビスコハク酸イミド、炭素数40〜400のアルキル基又はアルケニル基を分子中に少なくとも1個有するベンジルアミン、あるいは炭素数40〜400のアルキル基又はアルケニル基を分子中に少なくとも1個有するポリアミン、あるいはこれらのホウ素化合物、カルボン酸、リン酸等による変成品等が挙げられる。使用に際してはこれらの中から任意に選ばれる1種類あるいは2種類以上を配合することができる。 As the ashless detergent dispersant, any ashless detergent dispersant used for lubricating oils can be used. Examples of the ashless detergent dispersant include mono- or bissuccinimide having at least one linear or branched alkyl group or alkenyl group having 40 to 400 carbon atoms in the molecule, and alkyl group having 40 to 400 carbon atoms. Or a benzylamine having at least one alkenyl group in the molecule, a polyamine having at least one alkyl group or alkenyl group having 40 to 400 carbon atoms in the molecule, or a modification thereof with a boron compound, a carboxylic acid, a phosphoric acid or the like. Examples include products. At the time of use, one kind or two or more kinds arbitrarily selected from these can be blended.
酸化防止剤としては、フェノール系、アミン系等の無灰酸化防止剤、銅系、モリブデン系等の金属系酸化防止剤が挙げられる。酸化防止剤としては、具体的には、例えば、フェノール系無灰酸化防止剤としては、4,4’−メチレンビス(2,6−ジ−tert−ブチルフェノール)、4,4’−ビス(2,6−ジ−tert−ブチルフェノール)等が、アミン系無灰酸化防止剤としては、フェニル−α−ナフチルアミン、アルキルフェニル−α−ナフチルアミン、ジアルキルジフェニルアミン等が挙げられる。 Examples of the antioxidant include ashless antioxidants such as phenol and amine, and metal antioxidants such as copper and molybdenum. Specific examples of the antioxidant include 4,4′-methylenebis (2,6-di-tert-butylphenol) and 4,4′-bis (2,4) as phenol-based ashless antioxidants. 6-di-tert-butylphenol) and the like, and amine-based ashless antioxidants include phenyl-α-naphthylamine, alkylphenyl-α-naphthylamine, dialkyldiphenylamine and the like.
腐食防止剤としては、例えば、ベンゾトリアゾール系、トリルトリアゾール系、チアジアゾール系、又はイミダゾール系化合物等が挙げられる。 Examples of the corrosion inhibitor include benzotriazole-based, tolyltriazole-based, thiadiazole-based, and imidazole-based compounds.
泡消剤としては、例えば、25℃における動粘度が1000〜10万mm2/sのシリコーンオイル、フルオロシリコーンオイル、アルケニルコハク酸誘導体、ポリヒドロキシ脂肪族アルコールと長鎖脂肪酸のエステル、メチルサリチレートとo−ヒドロキシベンジルアルコール等が挙げられる。 Examples of the defoaming agent include silicone oil having a kinematic viscosity at 25 ° C. of 1000 to 100,000 mm 2 / s, fluorosilicone oil, alkenylsuccinic acid derivative, ester of polyhydroxy aliphatic alcohol and long chain fatty acid, and methyl salicylate. Examples thereof include rate and o-hydroxybenzyl alcohol.
摩擦調整剤としては、モリブデンジチオカーバメートやモリブデンジチオフォスフェートなどのコハク酸イミドモリブデン錯体や有機モリブデン酸のアミン塩等の有機モリブデン化合物のほか、基本構造として炭素数8以上30以下の直鎖アルキルと金属に吸着できる極性基を同じ分子内にもつ構造のものが挙げられる。極性基としては、アミンやポリアミン、アミドや、これらを同時に分子内に持つ、アミン化合物、脂肪酸エステル、脂肪酸アミド、脂肪酸、脂肪族アルコール、脂肪族エーテル、ウレア系化合物、ヒドラジド系化合物等尿素やアルケニルコハク酸イミドタイプ、エステル、アルコールやジオール、あるいはエステルと水酸基を同時にもつ、例えばモノアルキルグリセリンエステルなどが挙げられる。そのほかアミンと水酸基とを同じ分子内に持つ、たとえばアルキルアミンアフコシキアルコール等など様々である。 Friction modifiers include succinimide molybdenum complexes such as molybdenum dithiocarbamate and molybdenum dithiophosphate, and organic molybdenum compounds such as amine salts of organic molybdic acid. There is a structure having a polar group that can be adsorbed on in the same molecule. As the polar group, amines, polyamines, amides, amine compounds, fatty acid esters, fatty acid amides, fatty acids, aliphatic alcohols, aliphatic ethers, urea compounds, hydrazide compounds, etc., which have these simultaneously in the molecule, urea or alkenyl Examples thereof include succinimide type, ester, alcohol and diol, or monoalkyl glycerin ester having an ester and a hydroxyl group at the same time. In addition, there are various amines and hydroxyl groups in the same molecule, for example, alkylamine afkoshi alcohol.
潤滑油組成物が、流動点降下剤、摩耗防止剤、金属系清浄分散剤、無灰清浄分散剤、酸化防止剤、腐食防止剤、泡消剤及び摩擦調整剤よりなる群から選ばれる1種又は2種以上を含有する場合、それぞれの含有量は、潤滑油組成物の全量を基準として、0.01質量%以上10質量%以下であることが好ましい。また、潤滑油組成物が消泡剤を含有する場合、その含有量は、好ましくは0.0001質量%以上0.01質量%以下である。なお、潤滑油組成物を基油組成物として用いる場合は、基油組成物は実質的に粘度指数向上剤と潤滑油基油からなるものであってもよく、この場合、基油組成物中の粘度指数向上剤と潤滑油基油の合計含有量は、基油組成物の全量を基準として、例えば98質量%以上であることが好ましく、99質量%以上がより好ましく、99.5質量%以上がさらに好ましい。 The lubricating oil composition is one selected from the group consisting of pour point depressants, antiwear agents, metallic detergent dispersants, ashless detergent dispersants, antioxidants, corrosion inhibitors, defoamers and friction modifiers. Alternatively, when two or more kinds are contained, the content of each is preferably 0.01% by mass or more and 10% by mass or less based on the total amount of the lubricating oil composition. When the lubricating oil composition contains an antifoaming agent, its content is preferably 0.0001 mass% or more and 0.01 mass% or less. When the lubricating oil composition is used as a base oil composition, the base oil composition may consist essentially of a viscosity index improver and a lubricating base oil. In this case, the base oil composition The total content of the viscosity index improver and the lubricating base oil is, for example, preferably 98% by mass or more, more preferably 99% by mass or more, and more preferably 99.5% by mass, based on the total amount of the base oil composition. The above is more preferable.
潤滑油組成物は、上記の成分に加えて、本発明の重合体以外の粘度指数向上剤、さび止め剤、抗乳化剤、金属不活性化剤等をさらに含有することができる。 The lubricating oil composition may further contain a viscosity index improver other than the polymer of the present invention, a rust inhibitor, a demulsifier, a metal deactivator and the like in addition to the above components.
本発明の重合体以外の粘度指数向上剤は、具体的には非分散型又は分散型エステル基含有粘度指数向上剤であり、例として非分散型又は分散型ポリ(メタ)アクリレート系粘度指数向上剤、非分散型又は分散型オレフィン−(メタ)アクリレート共重合体系粘度指数向上剤、スチレン−無水マレイン酸エステル共重合体系粘度指数向上剤及びこれらの混合物等が挙げられる。これらの中でも非分散型又は分散型ポリ(メタ)アクリレート系粘度指数向上剤であることが好ましく、非分散型又は分散型ポリメタクリレート系粘度指数向上剤であることがより好ましい。その他に、非分散型又は分散型エチレン−α−オレフィン共重合体又はその水素化物、ポリイソブチレン又はその水素化物、スチレン−ジエン水素化共重合体及びポリアルキルスチレン等を挙げることができる。 The viscosity index improver other than the polymer of the present invention is specifically a non-dispersion type or dispersion type ester group-containing viscosity index improvement agent, and as an example, a non-dispersion type or dispersion type poly (meth) acrylate viscosity index improving agent. Agents, non-dispersed or dispersed olefin- (meth) acrylate copolymer-based viscosity index improvers, styrene-maleic anhydride copolymer-based viscosity index improvers, and mixtures thereof. Among these, the non-dispersion type or dispersion type poly (meth) acrylate viscosity index improver is preferable, and the non-dispersion type or dispersion type polymethacrylate viscosity index improver is more preferable. Other examples include non-dispersion type or dispersion type ethylene-α-olefin copolymers or hydrogenated products thereof, polyisobutylene or hydrogenated products thereof, styrene-diene hydrogenated copolymers and polyalkylstyrenes.
さび止め剤としては、例えば、石油スルホネート、アルキルベンゼンスルホネート、ジノニルナフタレンスルホネート、アルケニルコハク酸エステル、又は多価アルコールエステル等が挙げられる。 Examples of the rust preventive agent include petroleum sulfonate, alkylbenzene sulfonate, dinonylnaphthalene sulfonate, alkenyl succinic acid ester, and polyhydric alcohol ester.
抗乳化剤としては、例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルフェニルエーテル、又はポリオキシエチレンアルキルナフチルエーテル等のポリアルキレングリコール系非イオン系界面活性剤等が挙げられる。 Examples of the demulsifier include polyalkylene glycol-based nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, and polyoxyethylene alkylnaphthyl ether.
金属不活性化剤としては、例えば、イミダゾリン、ピリミジン誘導体、アルキルチアジアゾール、メルカプトベンゾチアゾール、ベンゾトリアゾール又はその誘導体、1,3,4−チアジアゾールポリスルフィド、1,3,4−チアジアゾリル−2,5−ビスジアルキルジチオカーバメート、2−(アルキルジチオ)ベンゾイミダゾール、又はβ−(o−カルボキシベンジルチオ)プロピオンニトリル等が挙げられる。 Examples of the metal deactivator include imidazoline, pyrimidine derivative, alkylthiadiazole, mercaptobenzothiazole, benzotriazole or its derivative, 1,3,4-thiadiazole polysulfide, 1,3,4-thiadiazolyl-2,5-bis. Examples thereof include dialkyldithiocarbamate, 2- (alkyldithio) benzimidazole, and β- (o-carboxybenzylthio) propionnitrile.
以下に実施例により本発明を詳細に説明するが、本発明はこれに限定されるものではない。なお、実施例、比較例中の「%」および「部」は、特に断りのない場合、それぞれ「質量%」および「質量部」を表す。 Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited thereto. In addition, "%" and "part" in Examples and Comparative Examples represent "mass%" and "part by mass", respectively, unless otherwise specified.
また、実施例では、便宜上、化合物について下記の略称を用いる。 In the examples, the following abbreviations for compounds are used for convenience.
LMI:ラウリルマレイミド(製造例1で合成した単量体)
SMI:ステアリルマレイミド(製造例2で合成した単量体)
MMA:メチルメタクリレート
SMA:ステアリルメタクリレート
SLMA:ラウリルメタクリレート/トリデシルメタクリレート=54/46(質量比)の混合物
(1)分析方法
(重合率)
本発明の各単量体成分の重合率は、ガスクロマトグラフィー(島津製作所社製、GC−2010plus)を用いて求めた。
LMI: lauryl maleimide (monomer synthesized in Production Example 1)
SMI: Stearyl maleimide (monomer synthesized in Production Example 2)
MMA: methyl methacrylate SMA: stearyl methacrylate SLMA: lauryl methacrylate / tridecyl methacrylate = 54/46 (mass ratio) mixture (1) Analytical method (polymerization rate)
The polymerization rate of each monomer component of the present invention was determined using gas chromatography (manufactured by Shimadzu Corporation, GC-2010plus).
測定条件は以下の通りである。
−カラム:GLサイエンス製 Inert Cap1(液相の膜厚:0.25μm、長さ:30m、内径:0.25mm)
−温度:40℃(5分保持)+40℃〜170℃(10℃/分)+170℃〜210℃(5℃/分)+210℃〜330℃(15℃/分)+330℃(20分保持)
−気化室温度:200℃
−検出器温度:350℃(FID)
−キャリアガス:ヘリウム(カラム流量1.33ml/分)
−注入量:0.5μl(スプリット法、スプリット比:30.0)
−内部標準試料:トリデカン
−希釈溶剤:酢酸エチル
各単量体とトリデカンを酢酸エチルに溶解させた検量線溶液を作成し、それらをガスクロマトグラフィーで測定し、ピーク面積から検量線を作成した。次いで、重合溶液とトリデカンを酢酸エチルに溶解させたサンプル溶液を作成し同様に測定した。内部標準法により、各単量体成分の重合率を求めた。
The measurement conditions are as follows.
-Column: GL Science Inert Cap1 (liquid phase film thickness: 0.25 μm, length: 30 m, inner diameter: 0.25 mm)
-Temperature: 40 ° C (hold 5 minutes) + 40 ° C to 170 ° C (10 ° C / min) + 170 ° C to 210 ° C (5 ° C / min) + 210 ° C to 330 ° C (15 ° C / min) + 330 ° C (hold 20 minutes)
-Vaporization chamber temperature: 200 ° C
-Detector temperature: 350 ° C (FID)
-Carrier gas: Helium (column flow rate 1.33 ml / min)
Injection volume: 0.5 μl (split method, split ratio: 30.0)
-Internal standard sample: tridecane-Diluting solvent: ethyl acetate A calibration curve solution was prepared by dissolving each monomer and tridecane in ethyl acetate, and they were measured by gas chromatography to prepare a calibration curve from the peak area. Then, a sample solution was prepared by dissolving the polymerization solution and tridecane in ethyl acetate, and the same measurement was performed. The polymerization rate of each monomer component was determined by the internal standard method.
(重量平均分子量および数平均分子量)
重合体の重量平均分子量と数平均分子量の測定は、下記の条件にて行った。
−装置:東ソー社製GPCシステム HLC−8320GPC ECOSEC
−カラム:東ソー社製、TSKgel GMHXL 2本
−展開溶媒:テトラヒドロフラン
−展開溶媒の流量:1.0ml/分
−標準試料:TSK標準ポリスチレン(東ソー社製、PS−オリゴマーキット)
−カラム温度:40℃
−サンプル濃度:0.5%
−注入量:200μl
(粘度指数)
100℃における動粘度が7.0mm2/秒となるように、基油(SK製:YUBASE4)に重合体を希釈し、JIS K2283の方法で測定した。粘度指数が230以上の場合を○、230未満の場合を×とした。
(Weight average molecular weight and number average molecular weight)
The weight average molecular weight and the number average molecular weight of the polymer were measured under the following conditions.
-Device: Tosoh GPC system HLC-8320GPC ECOSEC
-Column: Tosoh Corporation, TSKgel GMHXL 2 bottles-Developing solvent: tetrahydrofuran-Flow rate of developing solvent: 1.0 ml / min-Standard sample: TSK standard polystyrene (Tosoh Corporation, PS-oligomer kit)
-Column temperature: 40 ° C
-Sample concentration: 0.5%
-Injection volume: 200 μl
(Viscosity index)
The polymer was diluted with a base oil (YUBASE4 manufactured by SK) so that the kinematic viscosity at 100 ° C. was 7.0 mm 2 / sec, and measured by the method of JIS K2283. When the viscosity index was 230 or more, it was evaluated as ◯, and when it was less than 230, it was evaluated as x.
(せん断安定性)
100℃における動粘度が7.0mm2/秒となるように、基油(SK製:YUBASE4)に重合体を希釈し、以下の条件で超音波を照射した。
装置:Hielscher Ultrasonics社製 UP400S
設定:Amplitude=70%、Cycle=1
時間:10分
温度:100℃
せん断前後および基油の100℃における動粘度を測定し、SSI={1−(せん断後の動粘度−基油の動粘度)/(せん断前の動粘度−基油の動粘度)}×100の式で計算される値が、45未満である場合を○、45以上である場合を×とした。
(Shear stability)
The polymer was diluted with a base oil (YUBASE4 manufactured by SK) so that the kinematic viscosity at 100 ° C. was 7.0 mm 2 / sec, and ultrasonic waves were irradiated under the following conditions.
Device: Hielscher Ultrasonics UP400S
Settings: Amplitude = 70%, Cycle = 1
Time: 10 minutes Temperature: 100 ° C
The kinematic viscosities of the base oil before and after shearing and at 100 ° C. were measured, and SSI = {1- (kinematic viscosity after shearing−kinematic viscosity of base oil) / (kinematic viscosity before shearing−kinematic viscosity of base oil)} × 100 When the value calculated by the formula is less than 45, it is indicated as ◯, and when it is 45 or more, it is indicated as x.
(2)重合体の基油溶液の製造例
(製造例1)LMIの合成
温度計、冷却管および攪拌機を備えた500mlのフラスコに、無水マレイン酸51.48g(0.525mol)、キシレン272.88gを投入し、80℃で撹拌、溶解した。次いで、ラウリルアミン134.76g(0.50mol)、キシレン92.68gの混合溶液を滴下漏斗を用いて1時間かけて投入した後、80℃にて1時間撹拌、熟成した。ムース状の反応液をろ過し、ろ取した固体をキシレンでさらに洗浄した後、60℃で減圧乾燥し、白色固体のラウリルマレアミド酸を得た。
次いで得られたラウリルマレアミド酸42.5g(0.15mol)、酸化カルシウム168mg、トリエチルアミン5.3g、無水酢酸20.4g(0.2mol)を温度計、冷却管および攪拌機を備えた300mlのフラスコに投入した。80℃で3時間撹拌反応し、得られた固体を水洗ろ過した。さらに、メタノールで再結晶後、40℃で減圧乾燥し、微黄色のLMI15.88g(ラウリルマレアミド酸換算収率39.9%、ラウリルアミン換算収率12.0%)を得た。
(2) Production Example of Base Oil Solution of Polymer (Production Example 1) Synthesis of LMI In a 500 ml flask equipped with a thermometer, a condenser and a stirrer, 51.48 g (0.525 mol) of maleic anhydride and xylene 272. 88 g was added, and the mixture was stirred and dissolved at 80 ° C. Then, a mixed solution of 134.76 g (0.50 mol) of laurylamine and 92.68 g of xylene was added using a dropping funnel over 1 hour, and then the mixture was stirred and aged at 80 ° C. for 1 hour. The mousse-like reaction liquid was filtered, and the solid collected by filtration was further washed with xylene and then dried under reduced pressure at 60 ° C. to obtain white solid lauryl maleamic acid.
Then, the obtained lauryl maleamic acid 42.5 g (0.15 mol), calcium oxide 168 mg, triethylamine 5.3 g, and acetic anhydride 20.4 g (0.2 mol) were added to a 300 ml flask equipped with a thermometer, a condenser and a stirrer. I put it in. The mixture was reacted with stirring at 80 ° C. for 3 hours, and the obtained solid was washed with water and filtered. Further, after recrystallization from methanol, it was dried under reduced pressure at 40 ° C. to obtain 15.88 g of slightly yellow LMI (lauryl maleamic acid conversion yield 39.9%, lauryl amine conversion yield 12.0%).
(製造例2)SMIの合成
温度計、冷却管および攪拌機を備えた500mlのフラスコに、無水マレイン酸12.87g(0.131mol)、キシレン200gを投入し、100℃にて撹拌、溶解した。次いで、ステアリルアミン33.69g(0.125mol)、キシレン70gの50℃に加温した混合溶液を滴下漏斗にて1時間かけて投入した後、100℃で6時間撹拌、熟成した。70℃で反応液をろ過し、ろ取した固体をキシレンでさらに洗浄した後、60℃で減圧乾燥し、白色固体のステアリルマレアミド酸を得た。
次いで得られたステアリルマレアミド酸29.41g(0.08mol)、85%リン酸14.7g、キシレン100gを温度計、水分離管、冷却管および攪拌機を備えた300mlのフラスコに投入した。150℃で3時間撹拌反応し、得られた反応液を分液後、油層を水洗した。水洗後油層からキシレンを留去、メタノールで再結晶後、40℃で減圧乾燥し、微黄色のステアリルマレイミド12.91g(ステアリルマレアミド酸換算収率46.2%、ステアリルアミン換算収率29.6%)を得た。
(Production Example 2) Synthesis of SMI To a 500 ml flask equipped with a thermometer, a cooling tube and a stirrer, 12.87 g (0.131 mol) of maleic anhydride and 200 g of xylene were charged, and the mixture was stirred and dissolved at 100 ° C. Then, a mixed solution of 33.69 g (0.125 mol) of stearylamine and 70 g of xylene heated to 50 ° C. was added by a dropping funnel over 1 hour, and then the mixture was stirred and aged at 100 ° C. for 6 hours. The reaction solution was filtered at 70 ° C., the solid collected by filtration was further washed with xylene, and dried under reduced pressure at 60 ° C. to obtain white solid stearyl maleamic acid.
Then, 29.41 g (0.08 mol) of the obtained stearyl maleamic acid, 14.7 g of 85% phosphoric acid and 100 g of xylene were charged into a 300 ml flask equipped with a thermometer, a water separation tube, a cooling tube and a stirrer. After stirring and reacting at 150 ° C. for 3 hours, the resulting reaction solution was separated and the oil layer was washed with water. After washing with water, xylene was distilled off from the oil layer, recrystallized with methanol, and dried under reduced pressure at 40 ° C. to obtain 12.91 g of slightly yellow stearyl maleimide (stearyl maleamic acid conversion yield 46.2%, stearyl amine conversion yield 29. 6%) was obtained.
(実施例1)
撹拌装置、温度センサー、冷却管、窒素導入管、および滴下ロートを備えた反応容器に、MMA30質量部、SMA30質量部、LMI10質量部、SLMA30質量部、トルエン53.33質量部、酸化防止剤(アデカスタブ(登録商標)2112、ADEKA社製)0.05質量部、無水酢酸0.40質量部、ペンタエリスリトールテトラキス(メルカプトアセテート)0.05質量部を仕込み、これに窒素ガスを導入しつつ内容物を105℃まで昇温させた。重合開始剤として0.0258質量部のt−アミルパーオキシイソノナノエート(アルケマ吉富社製、ルペロックス(登録商標)570)とトルエン0.46質量部を混合した溶液を添加するとともに、前記重合開始剤0.103質量部をトルエン10.3質量部に溶解させた溶液を4時間かけて滴下しながら溶液重合を進行させ、さらに4時間の熟成を行った。
(Example 1)
In a reaction vessel equipped with a stirrer, a temperature sensor, a cooling pipe, a nitrogen introducing pipe, and a dropping funnel, 30 parts by mass of MMA, 30 parts by mass of SMA, 10 parts by mass of LMI, 30 parts by mass of SLMA, 53.33 parts by mass of toluene, and an antioxidant ( ADEKA STAB (registered trademark) 2112, manufactured by ADEKA) 0.05 parts by mass, acetic anhydride 0.40 parts by mass, pentaerythritol tetrakis (mercaptoacetate) 0.05 parts by mass are charged, and the contents are introduced while introducing nitrogen gas. Was heated to 105 ° C. As a polymerization initiator, 0.0258 parts by mass of t-amyl peroxyisononanoate (Arkema Yoshitomi Co., Luperox (registered trademark) 570) and 0.46 parts by mass of toluene were added, and the polymerization was started. A solution prepared by dissolving 0.103 parts by mass of the agent in 10.3 parts by mass of toluene was added dropwise over 4 hours to allow solution polymerization to proceed, followed by aging for 4 hours.
続いて、冷却管を冷却管および溜出液受器につなげたトの字管に取替え、基油(SK製:YUBASE4)233質量部を反応容器に投入した。バス温を150℃まで昇温した後、真空ポンプを用いて徐々に減圧し、トルエンを除去した。内温が142℃に到達してから30分後に解圧・冷却し、重合体1の基油溶液(重合体濃度30質量%)を得た。結果を表1に示す。 Subsequently, the cooling pipe was replaced with a V-shaped pipe connected to the cooling pipe and the distillate receiver, and 233 parts by mass of base oil (YUBASE4 manufactured by SK) was charged into the reaction vessel. After raising the bath temperature to 150 ° C., the pressure was gradually reduced using a vacuum pump to remove toluene. Thirty minutes after the internal temperature reached 142 ° C., decompression and cooling were performed to obtain a base oil solution of polymer 1 (polymer concentration 30% by mass). Table 1 shows the results.
(実施例2)
撹拌装置、温度センサー、冷却管、窒素導入管、および滴下ロートを備えた反応容器に、MMA35質量部、SMA30質量部、SMI10質量部、SLMA25質量部、トルエン32.3質量部、酸化防止剤(アデカスタブ(登録商標)2112、ADEKA社製)0.05質量部、無水酢酸0.40質量部、n−ドデシルメルカプタン0.05質量部を仕込み、これに窒素ガスを導入しつつ内容物を105℃まで昇温させた。重合開始剤として0.0258質量部のt−アミルパーオキシイソノナノエート(アルケマ吉富社製、ルペロックス(登録商標)570)とトルエン0.46質量部を混合した溶液を添加するとともに、前記重合開始剤0.103質量部をトルエン10.3質量部に溶解させた溶液を4時間かけて滴下しながら溶液重合を進行させ、さらに4時間の熟成を行った。
(Example 2)
In a reaction vessel equipped with a stirrer, a temperature sensor, a cooling pipe, a nitrogen introducing pipe, and a dropping funnel, 35 parts by mass of MMA, 30 parts by mass of SMA, 10 parts by mass of SMI, 25 parts by mass of SLMA, 32.3 parts by mass of toluene, and an antioxidant ( (Adeka Stab (registered trademark) 2112, manufactured by ADEKA) 0.05 parts by mass, acetic anhydride 0.40 parts by mass, and n-dodecyl mercaptan 0.05 parts by mass are charged, and the contents are heated to 105 ° C while introducing nitrogen gas. The temperature was raised to. As a polymerization initiator, 0.0258 parts by mass of t-amyl peroxyisononanoate (Arkema Yoshitomi Co., Luperox (registered trademark) 570) and 0.46 parts by mass of toluene were added, and the polymerization was started. A solution prepared by dissolving 0.103 parts by mass of the agent in 10.3 parts by mass of toluene was added dropwise over 4 hours to allow solution polymerization to proceed, followed by aging for 4 hours.
続いて、冷却管を冷却管および溜出液受器につなげたトの字管に取替え、基油(SK製:YUBASE4)233質量部を反応容器に投入した。バス温を150℃まで昇温した後、真空ポンプを用いて徐々に減圧し、トルエンを除去した。内温が142℃に到達してから30分後に解圧・冷却し、重合体2の基油溶液(重合体濃度30質量%)を得た。結果を表1に示す。 Subsequently, the cooling pipe was replaced with a V-shaped pipe connected to the cooling pipe and the distillate receiver, and 233 parts by mass of base oil (YUBASE4 manufactured by SK) was charged into the reaction vessel. After raising the bath temperature to 150 ° C., the pressure was gradually reduced using a vacuum pump to remove toluene. Thirty minutes after the internal temperature reached 142 ° C., decompression and cooling were performed to obtain a base oil solution of polymer 2 (polymer concentration 30% by mass). Table 1 shows the results.
(比較例1)
実施例1について、LMIの代わりにフェニルマレイミドを用いた以外は、実施例1と同様の操作を行い、重合体3の基油溶液(重合体濃度30%)を得た。重合体3は基油への溶解性が悪く不溶物が発生したため、粘度指数やせん断安定性の評価を行うことができなかった。結果を表1に示す。
(Comparative Example 1)
About Example 1, the same operation as in Example 1 was carried out except that phenylmaleimide was used instead of LMI to obtain a base oil solution of the polymer 3 (polymer concentration 30%). Since the polymer 3 had poor solubility in the base oil and an insoluble matter was generated, the viscosity index and the shear stability could not be evaluated. The results are shown in Table 1.
(比較例2)
撹拌装置、温度センサー、冷却管、窒素導入管、および滴下ロートを備えた反応容器に、MMA20質量部、SMA30質量部、トルエン46.7質量部、酸化防止剤(アデカスタブ(登録商標)2112、ADEKA社製)0.05質量部、n−ドデシルメルカプタン0.75質量部を仕込み、これに窒素ガスを導入しつつ内容物を85℃まで昇温させた。重合開始剤として0.25質量部の2,2−アゾビスジメチルバレロニトリル(ADVN)とトルエン2.25質量部を混合した溶液を添加するとともに、ADVN0.25質量部、n−ドデシルメルカプタン0.75質量部、MMA20質量部、SMA30質量部、トルエン46.7質量部およびトルエン50質量部の混合溶液を4時間かけて滴下した。2時間熟成後、トルエン2.3質量部に溶解させたADVN0.3質量部を反応容器に加え、さらに3時間反応させた。
続いて、冷却管を冷却管および溜出液受器につなげたトの字管に取替え、基油(SK製:YUBASE4)233質量部を反応容器に投入した。バス温を150℃まで昇温した後、真空ポンプを用いて徐々に減圧し、トルエンを除去した。内温が142℃に到達してから30分後に解圧・冷却し、重合体4の基油溶液(重合体濃度30質量%)を得た。結果を表1に示す。
(Comparative example 2)
In a reaction vessel equipped with a stirrer, a temperature sensor, a cooling tube, a nitrogen introducing tube, and a dropping funnel, 20 parts by mass of MMA, 30 parts by mass of SMA, 46.7 parts by mass of toluene, an antioxidant (Adeka Stab (registered trademark) 2112, ADEKA) 0.05 parts by mass and 0.75 parts by mass of n-dodecyl mercaptan were charged, and the contents were heated to 85 ° C. while introducing nitrogen gas. As a polymerization initiator, a solution prepared by mixing 0.25 parts by mass of 2,2-azobisdimethylvaleronitrile (ADVN) and 2.25 parts by mass of toluene was added, and 0.25 parts by mass of ADVN and n-dodecyl mercaptan of 0. A mixed solution of 75 parts by mass, 20 parts by mass of MMA, 30 parts by mass of SMA, 46.7 parts by mass of toluene and 50 parts by mass of toluene was added dropwise over 4 hours. After aging for 2 hours, 0.3 part by mass of ADVN dissolved in 2.3 parts by mass of toluene was added to the reaction vessel and the reaction was continued for another 3 hours.
Subsequently, the cooling pipe was replaced with a V-shaped pipe connected to the cooling pipe and the distillate receiver, and 233 parts by mass of base oil (manufactured by SK: YUBASE4) was charged into the reaction vessel. After raising the bath temperature to 150 ° C., the pressure was gradually reduced using a vacuum pump to remove toluene. Thirty minutes after the internal temperature reached 142 ° C., decompression and cooling were performed to obtain a base oil solution of polymer 4 (polymer concentration 30% by mass). The results are shown in Table 1.
(a)単位を有しMwが特定の範囲にある重合体を用いることによって、基油溶解性を維持しながら良好なせん断安定性をと高い粘度指数を示す粘度指数向上剤が得られた。 By using a polymer having the unit (a) and having an Mw within a specific range, a viscosity index improver having good shear stability and a high viscosity index while maintaining the solubility of the base oil was obtained.
本発明の重合体を含有する粘度指数向上剤を使用した潤滑油組成物は、従来の潤滑油組成物に比べて、基油溶解性を維持しながら良好なせん断安定性と高い粘度指数を示すことから、今後の自動車の省燃費性およびロングライフ性の要求に対応できるため、駆動系潤滑油、作動油、エンジン油に好適に用いることができる。 The lubricating oil composition using the viscosity index improver containing the polymer of the present invention exhibits good shear stability and a high viscosity index while maintaining solubility in the base oil, as compared with conventional lubricating oil compositions. Therefore, since it can meet future demands for fuel economy and long life of automobiles, it can be suitably used as drive system lubricating oil, hydraulic oil, and engine oil.
Claims (7)
前記重合体100質量部に対し、(a)単位の量および(c)単位の量の合計が、30質量部以上95質量部未満であり、
前記重合体の重量平均分子量(Mw)が20000以上500000未満である粘度指数向上剤。
The total amount of (a) units and (c) units is 30 parts by mass or more and less than 95 parts by mass with respect to 100 parts by mass of the polymer,
A viscosity index improver in which the weight average molecular weight (Mw) of the polymer is 20,000 or more and less than 500,000.
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