JP6676381B2 - マレイミド系単量体の共重合体の製造方法、並びに粘度指数向上剤、及び潤滑油組成物の製造方法 - Google Patents
マレイミド系単量体の共重合体の製造方法、並びに粘度指数向上剤、及び潤滑油組成物の製造方法 Download PDFInfo
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- JP6676381B2 JP6676381B2 JP2016003500A JP2016003500A JP6676381B2 JP 6676381 B2 JP6676381 B2 JP 6676381B2 JP 2016003500 A JP2016003500 A JP 2016003500A JP 2016003500 A JP2016003500 A JP 2016003500A JP 6676381 B2 JP6676381 B2 JP 6676381B2
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- 150000004668 long chain fatty acids Chemical class 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- SGLXWMAOOWXVAM-UHFFFAOYSA-L manganese(2+);octanoate Chemical compound [Mn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O SGLXWMAOOWXVAM-UHFFFAOYSA-L 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
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- UCUPUEARJPTGKU-UHFFFAOYSA-N octadecyl 3-sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCS UCUPUEARJPTGKU-UHFFFAOYSA-N 0.000 description 1
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- 125000000913 palmityl 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])C([H])([H])[H] 0.000 description 1
- 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
- NAKOELLGRBLZOF-UHFFFAOYSA-N phenoxybenzene;pyrrole-2,5-dione Chemical compound O=C1NC(=O)C=C1.O=C1NC(=O)C=C1.C=1C=CC=CC=1OC1=CC=CC=C1 NAKOELLGRBLZOF-UHFFFAOYSA-N 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
- 230000008569 process Effects 0.000 description 1
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- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
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- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
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- 238000000926 separation method Methods 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
- 238000010561 standard procedure Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
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- 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
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- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Lubricants (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
Description
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、前記共重合体の製造方法は、前記(a)成分の含量が、全単量体成分の合計100質量部に対して5質量部以上35質量部以下であることが好ましい。
前記共重合体は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前記単量体を潤滑油基油中で重合する工程で得られることが好ましい。
本発明は前記製造方法で共重合体を製造する共重合体製造工程と、該共重合体製造工程で得られた共重合体を70質量%以上含有する粘度指数向上剤を製造する工程とを有する、粘度指数向上剤の製造方法でもある。
本発明は、前記製造方法で粘度指数向上剤を製造する粘度指数向上剤製造工程と、該粘度指数向上剤製造工程で得られた粘度指数向上剤を基油に混合して潤滑油組成物を製造する工程とを有する、潤滑油組成物の製造方法でもある。
本発明は、単量体(a)成分を必須成分として含む単量体を潤滑油基油中で重合して重合体を得る工程を有する共重合体の製造方法であって、スチレン系単量体を使用する場合は、該重合体100質量部に対しスチレン系単量体由来の単位が2質量部以下であることを特徴とする共重合体の製造方法である。
単量体(a)成分として、上記Xの内、分岐状のアルキル基は芳香環を有するアルキル基を有していてもよい。環状のアルキル基としては、ベンジル基などの芳香環を有するアルキル基、シクロヘキシル基などのシクロアルキル基が好ましい。アリール基としては、フェニル基、ナフチル基や芳香環の水素が置換されたアリール基が好ましい。
単量体(a)成分の含量は、全単量体成分の合計100質量部に対して、0.5質量部以上35質量部以下であり、好ましくは2質量部以上35質量部以下、より好ましくは5質量部以上35質量部以下、特に好ましくは5質量部以上30質量部以下である。上記数値範囲の単量体(a)成分を用いた重合体を含有する粘度指数向上剤は、基油への溶解性を確保したまま、せん断安定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、金属表面の磨耗抑制等の効果が期待される。
単量体(c)成分の具体例としては、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、ドデシル(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、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、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。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、2−エチルヘキシル(メタ)アクリレート、ドデシル(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。なお、上記単量体(b)は単独で使用してもよいし、2種以上を併用してもよい。
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、N,N−ジメチル(メタ)アクリルアミド、アクリロイルモルフォリンが好ましい。
必須成分である(a)、(b)、(c)成分以外のラジカル重合性単量体(d)に含まれる多官能単量体由来の単位は、重合体100質量部に対し0質量部以上5質量部以下であることが好ましく、より好ましくは0質量部以上3質量部以下であり、さらに好ましくは0質量部以上2質量部以下である。この場合、重合体が星型構造や架橋構造をとることにより、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。
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200℃以下が好ましく、25℃〜150℃が特に好ましい。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。
(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。
また、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。
本発明により得られる共重合体を粘度指数向上剤として用い、潤滑油組成物とする際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、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。
本発明に用いる潤滑油基油は、潤滑油基油100質量部の内、パラフィンの含有量が60質量部以上90質量部以下であることが好ましく、より好ましくは65質量部以上85質量部以下であり、70質量部以上80質量部以下であることが特に好ましい。また、潤滑油基油100質量部の内、ナフテンの含有量が15質量部以上40質量部以下であることが好ましく、より好ましくは20質量部以上35質量部以下、さらには25質量部以上30質量部以下であることが特に好ましい。潤滑油基油の組成がこれらの範囲である時、熱安定性、光安定性に優れるだけでなく、所望の粘度への調整が容易である。また、潤滑油基油の粘度指数と低温特性のバランスが良好となる。
重合体に関する分析および評価を、以下の方法で行った。
(マレイミド系単量体重合率)
重合率の測定には、ガスクロマトグラフィー(島津製作所製、GC2010)を用いた。測定条件は以下のとおりである。
温度:
注入口温度:200℃
検出器温度:350℃
キャリアガス:ヘリウム(カラム流量1.39mL/分)
注入量:0.5μL
内部標準試料:トリデカン
希釈溶剤:p−キシレン
具体的には、予め、重合に用いる各単量体とトリデカンとをp−キシレンに溶解させた検量線溶液を作製し、当該溶液を上記測定条件のガスクロマトグラフィーで測定して得たピーク面積から検量線を作成した。次に、測定対象物である重合液とトリデカンとをp−キシレンに溶解させた測定試料を作製し、当該試料を上記測定条件のガスクロマトグラフィーで測定して、作成した検量線を用いた内部標準法により、重合液中の残存単量体の含有率を求め、重合開始前の単量体量含有率との比によって重合率を算出した。
(重量平均分子量)
システム:東ソー製GPCシステム HLC−8220
測定側カラム構成:
・ガードカラム:東ソー製、TSKguardcolumn SuperHZ−L
・分離カラム:東ソー製、TSKgel SuperHZM−M
リファレンス側カラム構成
・リファレンスカラム:東ソー製、TSKgel SuperH−RC
展開溶媒:クロロホルム(和光純薬工業製、特級)
展開溶媒の流量:0.6mL/分
標準試料:TSK標準ポリスチレン(東ソー製、PS−オリゴマーキット)
カラム温度:40℃
(粘度指数)
100℃における動粘度が7.0mm2/sとなるように、基油(SK製 YUBASE 4)に重合体を希釈し、JIS K2283の方法で測定した。
(せん断安定性)
100℃における動粘度が7.0mm2/sとなるように、基油(SK製 YUBASE 4)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製 UP400S
設定:Amplitude=70%、Cycle=1
時間:5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。
(臭気)
重合終了後の液10gを100mlスクリュー管に取り、蓋をして120℃で1時間加熱した後、蓋をとって臭気を確認し、酸成分由来の臭気がした場合を×、臭気がしなかった場合を○とした。
(SP値)
重合体のSP値(溶解度パラメーター)を、アクセルリス社製のMaterials Studio(登録商標) Ver.6.1 MS−Synthiaモジュールを用いて計算した。まず、モノマー構造を作成し、繰り返し構造を定義した。定義したモノマー構造を用いてMS−Synthiaモジュールで高分子物性(溶解度パラメーター等)を計算した。MS−Synthiaモジュールは定量的構造物性相関(QSPR:Quantitave Structure Property Relationships)を用いることにより高分子の物性を計算できるソフトウェアであり、グラフ理論から得られる結合性指数を用いてモノマー構造から高分子の物性を計算することができる。詳細な理論は次の文献に記載されており、当該記載が本願に参考のため援用される:Jozef Bicerano、「Prediction of Polymer Properties,3rd Edition」、Marcel Dekker社発刊。今回は、MS−Synthiaで計算できるBiceranoが改良したFedors法とvan Krevelen法のSP値(溶解度パラメーター)のうち、Fedors法の値を使用した。
(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、メチルメタクリレート(MMA)20質量部、ステアリルメタクリレート(StMA)30質量部、N−フェニルマレイミド(PMI)10質量部、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(SLMA)40質量部、基油(SK製 YUBASE 4)143.6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0.0774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)と基油(SK製 YUBASE 4)1.38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0.034質量部を基油(SK製 YUBASE 4)3.40質量部に溶解させた溶液を2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。
実施例1において、PMI10質量部をシクロヘキシルマレイミド(CHMI)10質量部に、MMAを25質量部に、SLMAを35質量部に変更した以外は同様の操作を行い、重合体の基油溶液(重合体濃度30質量%)を得た。結果を表1に示す。
(実施例3)
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、StMA30質量部、PMI10質量部、SLMA40質量部、基油(SK製 YUBASE 4)61.2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)と基油(SK製 YUBASE 4)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0.205質量部を基油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。
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、StMA30質量部、PMI10質量部、SLMA40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、およびトルエン60.8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0.205質量部をトルエン20.5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。
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、MMA25質量部、StMA40質量部、PMI10質量部、SLMA25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、およびトルエン27.4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。
比較例2において、無水酢酸を添加しない以外は同様の操作を行い、重合体の基油溶液(重合体濃度30質量%)を得た。結果を表1に示す。
Claims (6)
- マレイミド系単量体(以下、「(a)成分」と称する)を必須成分として含む単量体を潤滑油基油中で重合して重合体を得る工程を有する共重合体の製造方法であって、スチレン系単量体を使用する場合は、該重合体100質量部に対しスチレン系単量体由来の単位が2質量部以下であることを特徴とする共重合体の製造方法。
- 前記(a)成分の含量が、全単量体成分の合計100質量部に対して5質量部以上35質量部以下であることを特徴とする請求項1に記載の共重合体の製造方法。
- 前記(a)成分に加え、(b)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、(c)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)アクリレートを含む前記単量体を潤滑油基油中で重合する工程を有することを特徴とする請求項1または2に記載の共重合体の製造方法。
- 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前記単量体を潤滑油基油中で重合する工程を有することを特徴とする請求項1〜3のいずれか1項に記載の共重合体の製造方法。
- 請求項1〜4のいずれか1項に記載の製造方法で共重合体を製造する共重合体製造工程と、
該共重合体製造工程で得られた共重合体を70質量%以上含有する粘度指数向上剤を製造する工程と
を有する、粘度指数向上剤の製造方法。 - 請求項5に記載の製造方法で粘度指数向上剤を製造する粘度指数向上剤製造工程と、
該粘度指数向上剤製造工程で得られた粘度指数向上剤を基油に混合して潤滑油組成物を製造する工程と
を有する、潤滑油組成物の製造方法。
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