JP2019520445A - 耐摩耗コポリマーおよび潤滑剤組成物 - Google Patents
耐摩耗コポリマーおよび潤滑剤組成物 Download PDFInfo
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- JP2019520445A JP2019520445A JP2018560548A JP2018560548A JP2019520445A JP 2019520445 A JP2019520445 A JP 2019520445A JP 2018560548 A JP2018560548 A JP 2018560548A JP 2018560548 A JP2018560548 A JP 2018560548A JP 2019520445 A JP2019520445 A JP 2019520445A
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 54
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
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- KISVAASFGZJBCY-UHFFFAOYSA-N methyl undecenate Chemical compound COC(=O)CCCCCCCCC=C KISVAASFGZJBCY-UHFFFAOYSA-N 0.000 description 3
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- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 2
- 101100407030 Arabidopsis thaliana PAO2 gene Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004185 ester group Chemical group 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 238000004519 manufacturing process Methods 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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- CHWMPPNDIBLYMB-UHFFFAOYSA-N n',n'-bis(prop-2-enyl)ethane-1,2-diamine Chemical compound NCCN(CC=C)CC=C CHWMPPNDIBLYMB-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 125000001196 nonadecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 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
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- 125000004079 stearyl 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])C([H])([H])[H] 0.000 description 1
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/10—Vinyl esters of monocarboxylic acids containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C08F4/36—Per-compounds with more than one peroxy radical
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/14—Monomers containing five or more carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
- C10M143/08—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M145/08—Vinyl esters of a saturated carboxylic or carbonic acid
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
- C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
潤滑剤は、表面間の摩擦を減少させる組成物である。2つの表面間の運動の自由を可能にし、かつ該表面の機械的摩耗を減少させることに加えて、潤滑剤は、該表面の腐食を抑制することもできるおよび/または熱または酸化による該表面の損傷を抑制することもできる。潤滑剤組成物の例は、エンジン油、変速機油、ギヤー油、工業用潤滑油、および金属加工油を包含するが、しかしこれらに限定されない。
これらの課題、ならび明示的に述べられていないが、しかし本明細書の導入部によって議論された関係から直接的に誘導または認識できるさらなる課題は、以下のものを含むコポリマーによって達成される:
a)式(I)
x=6〜10である]の1種以上の化合物に由来する単位、該コポリマーの全質量を基準として、0.1質量%〜20質量%、
および
b)アルキル基が炭素原子1〜40個を有する1種以上のアルキル(メタ)アクリレートに由来する単位、該コポリマーの全質量を基準として、60質量%〜99.9質量%。
末端に酸またはエステル官能基を有する式(I)の化合物に由来する1個の単位または1個を超える単位を含むコポリマーが、潤滑剤組成物に添加される際に改善された摩耗性能を提供することが、意外なことに見出された。該官能基と該ポリマー主鎖との間にアルキルスペーサーを用いることにより、高い性能が低い官能化度で達成される、すなわち、所望の摩耗性能を達成するためのモノマーがあまり必要とされない。
(i)式(II)
および
(ii)式(III)
および
(iii)式(IV)
を含む。
a.式(I)
x=6〜10である]の1種以上の化合物、
b.アルキル基が炭素原子1〜40個を有する1種以上のアルキル(メタ)アクリレート、および任意に
c.式CnH2n[式中、n=8〜12である]の1種以上の非官能化α−オレフィン
を含む。
メチル10−ウンデセノエート70gおよび1−デセン137gを、1L四つ口丸底フラスコ中に装入した。反応混合物を、C−撹拌棒を用いて撹拌し、窒素で不活性化し、かつ140℃に加熱した。モノマーフィードは、C12〜C15メタクリレート493gを含んでいた。開始剤フィードは、2,2−ビス(t−ブチルペルオキシ)ブタン9.4gであった。該混合物が設定値温度に達したら、7時間のワンパスでのモノマーフィードおよび11時間のワンパスでの開始剤フィードを開始した。残存モノマーを、生じたポリマーについてガスクロマトグラフィーにより測定して、完全なモノマー転化を確実にした。未反応α−オレフィンモノマーの残量を、回転蒸発器により100℃および圧力15mmHg未満で除去した。
例2〜13を、例1と同じようにして製造したが、ただし、モノマーの質量比を、第1表に従って変更した。該α−オレフィンモノマーを常に最初に該反応器に装入し、かつ該(メタ)アクリレートモノマーおよび該開始剤を、設定期間にわたって供給した。分子量および動粘度は、多様なモノマー&開始剤フィード時間を用いてまたは該反応混合物中でのより大きな分率のα−オレフィンを使用することにより、制御することができる。例えば、例6および13は、同じ反応混合物を有する。該モノマーフィード時間を7時間(例6)から5時間(例13)まで変更することにより、動粘度は、206cStから321cStまで増大し、このことは、9400g/molから14700g/molへの質量平均分子量の変化にも反映される。
比較例1を、例1と同じようにして製造したが、ただし、その質量比またはモノマーは第1表に従った。
比較例2は、商業的に入手可能な高粘度のグループIVベースフルード(Synfluid(登録商標) PAO100)であって、1−デセンのホモポリマーである。
比較例3を、米国特許第8349779号明細書(US 8,349,779 B2)に従って、氷状メタクリル酸を用いて製造し、これは、COOH酸基を有するが、しかしそのメタクリレート基間にアルキルスペーサーを有していないモノマーである。
比較例4を、米国特許出願公開第2012/0245063号明細書(US 2012/0245063 A1)の例6に従って製造した。
cSt=センチストークス
AMA=アルキルメタクリレート
PAO=ポリα−オレフィン
IDMA=イソデシルメタクリレート
LIMA=LIAL 125アルコールから製造されたメタクリレートエステル
PAO2=Synfluid(登録商標) PAO2(商業的に入手可能な低粘度のグループIVベースオイルであって、1−デセンダイマーである)
PAO100=Synfluid(登録商標) PAO100(商業的に入手可能な高粘度のグループIVベースオイルであって、1−デセンのホモポリマーである)。
Claims (14)
- 前記コポリマーがさらに、
c)式CnH2n[式中、n=8〜12、好ましくはn=10である]の1種以上の非官能化α−オレフィンに由来する単位
を含む、請求項1に記載のコポリマー。 - 式(I)の1種以上の化合物に由来する前記単位中で、R=HまたはCH3、好ましくはR=Hである、請求項1または2に記載のコポリマー。
- 式(I)の1種以上の化合物に由来する前記単位中で、x=8である、請求項1〜3のいずれか1項に記載のコポリマー。
- 前記コポリマーが、式(I)の1種以上の化合物に由来する前記単位を、前記コポリマーの全質量を基準として、0.5質量%〜20質量%の全量で含む、請求項1〜4のいずれか1項に記載のコポリマー。
- 前記コポリマーが、1種以上のアルキル(メタ)アクリレートに由来する前記単位を、前記コポリマーの全質量を基準として、60質量%〜97質量%の全量で含む、請求項1〜5のいずれか1項に記載のコポリマー。
- 1種以上のアルキル(メタ)アクリレートに由来する前記単位が、
(i)式(II)
および
(ii)式(III)
および
(iii)式(IV)
を含む、請求項1〜6のいずれか1項に記載のコポリマー。 - 前記コポリマーが、式CnH2n[式中、n=8〜12である]の1種以上の非官能化α−オレフィンに由来する単位を、前記コポリマーの全質量を基準として、0.5質量%〜40質量%、好ましくは0.5質量%〜30質量%、より好ましくは3質量%〜30質量%の全量で含む、請求項2〜8のいずれか1項に記載のコポリマー。
- 請求項1〜9のいずれか1項に記載のコポリマーを含む、潤滑剤組成物。
- 前記潤滑剤組成物の全質量を基準として、0.01質量%〜50質量%、好ましくは0.5質量%〜40質量%の前記コポリマーを含む、請求項11に記載の潤滑剤組成物。
- 潤滑剤組成物における、摩耗を減少させるための、請求項1〜9のいずれか1項に記載のコポリマーの使用。
- 自動変速機油、無段変速機油、エンジン油、ギヤー油、または作動油としての、請求項11または12に記載の潤滑剤組成物の使用。
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EP16172136.0 | 2016-05-31 | ||
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4856613A (ja) * | 1971-09-13 | 1973-08-09 | ||
JP2005248157A (ja) * | 2003-12-05 | 2005-09-15 | Daikin Ind Ltd | 常温硬化性水性組成物 |
JP2007532703A (ja) * | 2004-04-08 | 2007-11-15 | ローマックス アディティヴス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 摩耗防止性の改善のための水素結合形成性の官能性を有するポリマー |
US20120264662A1 (en) * | 2011-03-24 | 2012-10-18 | Dibiase Stephen A | Functionalized monomers |
US20140274843A1 (en) * | 2013-03-14 | 2014-09-18 | Elevance Renewable Sciences, Inc. | Lubricant compositions including alpha-olefin copolymers |
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EP1379617B1 (en) * | 2001-04-11 | 2006-12-13 | The Lubrizol Corporation | Process for lubricating a driveline using lubricants containing olefin copolymer and acrylate copolymer |
US7314904B2 (en) | 2003-06-18 | 2008-01-01 | Baker Hughes Incorporated | Functionalized polyalphaolefins |
US20050101496A1 (en) | 2003-11-06 | 2005-05-12 | Loper John T. | Hydrocarbyl dispersants and compositions containing the dispersants |
DE102004018093A1 (de) * | 2004-04-08 | 2005-10-27 | Rohmax Additives Gmbh | Polymere mit H-Brücken bildenden Funktionalitäten |
US7560420B2 (en) | 2004-12-23 | 2009-07-14 | Rohmax Additives Gmbh | Oil composition for lubricating an EGR equipped diesel engine and an EGR equipped diesel engine comprising same |
CA2567235A1 (en) * | 2006-11-07 | 2008-05-07 | Ciba Specialty Chemicals Holding Inc. | Methacrylate copolymer pour point depressants |
EP2109659B1 (en) * | 2007-01-30 | 2019-06-12 | The Lubrizol Corporation | Dispersant combination for improved transmission fluids |
US20140113847A1 (en) | 2012-10-24 | 2014-04-24 | Exxonmobil Research And Engineering Company | High viscosity index lubricating oil base stock and viscosity modifier combinations, and lubricating oils derived therefrom |
WO2014150533A1 (en) | 2013-03-14 | 2014-09-25 | Elevance Renewable Sciences, Inc. | High-viscosity alpha-olefin copolymer compositions and methods of making and using the same |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4856613A (ja) * | 1971-09-13 | 1973-08-09 | ||
JP2005248157A (ja) * | 2003-12-05 | 2005-09-15 | Daikin Ind Ltd | 常温硬化性水性組成物 |
JP2007532703A (ja) * | 2004-04-08 | 2007-11-15 | ローマックス アディティヴス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 摩耗防止性の改善のための水素結合形成性の官能性を有するポリマー |
US20120264662A1 (en) * | 2011-03-24 | 2012-10-18 | Dibiase Stephen A | Functionalized monomers |
US20140274843A1 (en) * | 2013-03-14 | 2014-09-18 | Elevance Renewable Sciences, Inc. | Lubricant compositions including alpha-olefin copolymers |
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