JP2011127119A - ポリマーにおける改良 - Google Patents
ポリマーにおける改良 Download PDFInfo
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- JP2011127119A JP2011127119A JP2010283973A JP2010283973A JP2011127119A JP 2011127119 A JP2011127119 A JP 2011127119A JP 2010283973 A JP2010283973 A JP 2010283973A JP 2010283973 A JP2010283973 A JP 2010283973A JP 2011127119 A JP2011127119 A JP 2011127119A
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- formula
- alkyl group
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
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- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Abstract
Description
燃料の温度が低下して流動点に近づくと、ライン及びポンプにより燃料を輸送する際に困難が生じる。更に、形成されるワックス結晶は、流動点を超える温度で燃料ライン、スクリーン、及びフィルターを詰まらせる傾向がある。これらの問題は当業者によく認知されており、様々な添加剤が提案されていて、それらのうちの多くは燃料油の流動点を低下させるために商業的に使用されている。同様に、実際に形成されるワックス結晶の大きさを低減し、形を変更するために他の添加剤が提案され、商業的に使用されている。フィルターを詰まらせることがより少ないため、より小さな大きさの結晶が好ましい。主にアルカンワックスであるディーゼル燃料からのワックス、及び植物由来の燃料中のn−アルカン酸メチルは、プレートレット(platelet)として結晶化する。特定の添加剤はこれを阻害し、ワックスに針状の晶相を帯びさせ、結果として得られる針状結晶を、プレートレットよりもフィルターを通過させやすくし、或いはフィルター上に結晶の多孔質層を形成させやすくする。他の添加剤もまた、ワックス結晶を燃料中に懸濁させ、沈殿を低減させ、それ故、閉塞を予防することにつなげる効果を有する。
好ましくは、R3は−OCOR6を示す。
アルキル基R6は、直鎖状であってもよく、C3又はそれ以上である場合には、分岐していてもよい。好ましくは、R6は、C1からC8のアルキル基を示す。好ましい実施態様においては、R6はメチルである。
存在する場合、アルキル基R15及びR16は、直鎖状でも分岐していてもよいが、好ましくは直鎖状である。好ましくは、存在する場合、R15及びR16は同一であり、それぞれ直鎖状のC12からC14アルキル基を示す。好ましい実施態様においては、R15及びR16が存在する場合、それらはそれぞれ直鎖状のC12アルキル基である。
好ましくは、R4は水素原子である。
好ましい実施態様においては、Xは、式IVの基を示す。好ましくは、R7は、水素原子であり、R8は、メチル基であり、mは、1から6の整数、例えば、1、2、又は3であり、nは、6から18の整数、例えば、9、10、11、12、13、14、15、又は16である。
別の実施態様においては、Xは式Vの基を示す。好ましくは、R9は、C2アルキル架橋であり、R10及びR11は、共にメチルであり、qは0である。
好ましくは、Yは、式IVの基を示す(ここで、R7は水素原子であり、R8はメチル基であり、mは1から6の整数、例えば、1、2、又は3であり、nは、6から18の整数、例えば、9、10、11、12、13、14、15、又は16である)。
式VIIの構造単位が存在する場合、アルキル基R13は、直鎖状であっても分岐していてもよいが、好ましくは直鎖状である。好ましくは、R13は、直鎖状のC12からC16のアルキル基、例えば、直鎖状のC12アルキル基、又は直鎖状のC14アルキル基を示す。
好ましい態様においては、ポリマーは、式I、II、及びIIIaの構造単位を有し、ここで、Xは、式IVの基を示す。
より好ましい実施態様においては、ポリマーは、式I、II、及びIIIaの構造単位からなり、ここで、Xは、式IVの基を示す。
別の好ましい実施態様においては、ポリマーは、式I、II、及びIIIbの構造単位を有する。
より好ましい実施態様においては、ポリマーは、式I、II、及びIIIbの構造単位からなる。
別の好ましい実施態様においては、ポリマーは、式I、II、及びIIIaの構造単位を有し、ここで、Xは式Vの基を示す。
より好ましい実施態様においては、ポリマーは、式I、II、及びIIIaの構造単位からなり、ここで、Xは、式Vの基を示す。
別の好ましい実施態様においては、ポリマーは、式I、II、IIIb、及びVIIの構造単位を有する。
より好ましい実施態様においては、ポリマーは、式I、II、IIIb、及びVIIの構造単位からなる。
好ましくは、式IIの単位は、モル換算でポリマーの5%から70%を占め、より好ましくは10%から50%を占める。
好ましくは、式IIIaの単位は、存在する場合、モル換算でポリマーの5%から60%を占め、より好ましくは10%から50%を占める。
好ましくは、式IIIbの単位は、存在する場合、モル換算でポリマーの5%から70%を占め、より好ましくは10%から60%を占める。
好ましくは、式VIIの単位は、存在する場合、モル換算でポリマーの10%から50%を占め、より好ましくは15%から40%を占める。
第三の側面によれば、本発明は、燃料油の低温特性を改善するための第一の側面のポリマーの使用を提供する。
燃料油は、例えば、石油系燃料油、特に中間留分燃料油であってもよい。そのような蒸留燃料油は、一般的には110℃から500℃、例えば150℃から400℃の範囲内で沸騰する。
本発明は、広い温度範囲で沸騰する蒸留物(即ち、ASTM D-86で測定した90%から20%の沸点差が50℃以上であるもの)を含め、全てのタイプの中間留分燃料油に適用することができる。
燃料油は、大気圧蒸留物若しくは真空蒸留物、クラッキングされたガス油、又は直留蒸留物並びに熱分解蒸留物及び/又は触媒分解蒸留物の任意の比率の混合物を含んでいてもよい。最も一般的な石油留出燃料は、ケロシン、ジェット燃料、ディーゼル燃料、暖房油、及び重質燃料油である。暖房油は大気圧直留物であってもよく、又は真空ガス油若しくはクラッキングされたガス油又はその両方を含んでいてもよい。燃料は、フィッシャー−トロプシュ法により得られる多量又は少量の成分を含んでいてもよい。FT燃料としても知られるフィッシャー−トロプシュ燃料は、ガスツーリキッド燃料(gas to liquid fuel)、石炭変換燃料及び/又はバイオマス変換燃料として記載されるものを含む。そのような燃料を製造するため、合成ガス(CO+H2)が最初に生成され、次いで、フィッシャー−トロプシュ法によりノルマルパラフィン及びオレフィンに変換される。ノルマルパラフィンは、次いで触媒的クラッキング/改質又は異性化、水素化分解、及び水素化異性化等の方法により変換され、iso−パラフィン類、シクロ−パラフィン類、及び芳香族化合物等の様々な炭化水素を得てもよい。結果として得られるFT燃料はそのまま使用することもできるし、本明細書に記載したもののような他の燃料成分及び他の燃料型と共に使用することができる。
動物材料又は植物材料から得られる油の例としては、ナタネ油、コリアンダー油、ダイズ油、綿実油、ヒマワリ油、ヒマシ油、オリーブ油、ピーナッツ油、トウモロコシ油、アーモンド油、パーム核油、ココナッツ油、カラシ油、ジャトロファ(jatropha)油、牛脂、及び魚油を挙げることができる。更なる例としては、トウモロコシ、ジュート、ゴマ、シアの実、グラウンドナッツ(ground nut)から得られる油、及び亜麻仁油を挙げることができ、当業者に知られた方法によりそれらから得ることができる。グリセロールで部分的にエステル化された脂肪酸の混合物であるナタネ油は、大量に入手可能で、ナタネから搾るという単純な方法で得ることができる。使用済みキッチン油等の再生油もまた好適である。
脂肪酸のアルキルエステルとしては、例えば、市販の混合物として以下のものが考慮される:例えば、ラウリン酸、ミリスチン酸、パルミチン酸、パルミトレイン酸、ステアリン酸、オレイン酸、エライジン酸、ペトロセリン酸、リシノール酸、エレオステアリン酸、リノール酸、リノレン酸、エイコサン酸、ガドレイン酸、ドコサン酸、又はエルカ酸等、12個から22個の炭素原子を有する脂肪酸のエチル、プロピル、ブチル、及び特にはメチルエステルであって、50から150、特には90から125のヨウ素価を有するもの。特に有利な性質を有する混合物は、主に、即ち少なくとも50質量%の、16個から22個の炭素原子、及び1、2、又は3個の二重結合を有する脂肪酸のメチルエステルを含むものを挙げることができる。好ましい脂肪酸のアルキルエステルは、オレイン酸、リノール酸、リノレン酸、及びエルカ酸のメチルエステルを挙げることができる。
前記の種類の市販の混合物は、例えば、低級(概ね、C1からC6)脂肪族アルコールとのエステル交換反応による、動物及び植物油脂の開裂及びエステル化により得られる。脂肪酸のアルキルエステルを製造するためには、20%未満の、低レベルの飽和脂肪酸を含み、130未満のヨウ素価を有する油脂から出発することが有利である。以下のエステル又は油の混合物が好適である:例えば、ナタネ、ヒマワリ、コリアンダー、ヒマシ、ダイズ、ピーナッツ、綿実、牛脂等。80質量%を超える、18個の炭素原子を有する不飽和脂肪酸を有する、ある種のナタネ油に基づく脂肪酸のアルキルエステルが特に好適である。
上記の油の全てはバイオ燃料として使用することができるが、好ましいものは、植物油の誘導体であり、特に好ましいバイオ燃料はナタネ油、綿実油、ダイズ油、ヒマワリ油、オリーブ油、又はパーム油のアルキルエステル誘導体であり、ナタネ油のメチルエステルが特に好ましい。
バイオ燃料は、一般的には石油から得られた油と組み合わせて使用される。本発明は、任意の比率のバイオ燃料と石油から得られた燃料との組み合わせに対しても適用することができる。そのような燃料は、度々、Bx燃料と呼ばれ、ここでxはバイオ燃料−石油混合物におけるバイオ燃料の質量%を示す。例としては、xが2以上、好ましくは5以上、例えば10まで、25まで、50まで、又は95までである燃料が挙げられる。好ましくは、そのようなBx燃料におけるバイオ燃料成分は、脂肪酸アルキルエステル、最も好ましくは脂肪酸メチルエステルを含む。
燃料油は、石油から得られたものであっても、植物から得られたものであっても、動物から得られたものであっても、低い硫黄含量を有する。典型的には、燃料油の硫黄含量は500ppm(質量100万分率)未満である。好ましくは、燃料油の硫黄含量は、100ppm未満であり、例えば50ppm未満である。更に低い硫黄含量を有する燃料油、例えば、20ppm未満のもの、10ppm未満のものもまた好適である。
燃料油に存在するポリマーの量は、燃料油の種類、及び燃料油に要求される低温特性によって異なる。好適には、ポリマーは、燃料油の質量に基づいて、燃料中に10質量ppmから5,000質量ppmの量で、好ましくは10質量ppmから1,000質量ppmの量で、より好ましくは50質量ppmから500質量ppmの量で存在する。
本発明のポリマーは、直接燃料油に提供されてもよく、添加剤濃縮物の形で燃料油に提供されてもよい。
本発明のポリマーは、潤滑油に、流動性向上剤又は流動点降下剤として潤滑油における用途を見出してもよい。
燃料油の低温特性を変更する他の添加剤を、本発明のポリマーと組み合わせてもよい。好適な材料は当業者に知られており、エチレン−不飽和エステルの共重合体及び三元重合体、例えば、エチレン−酢酸ビニル共重合体、エチレン−2−エチルヘキサン酸ビニル共重合体、及びエチレン−ネオデカン酸ビニル共重合体、エチレン−酢酸ビニル−2−エチルヘキサン酸ビニル三元重合体、エチレン−酢酸ビニル−ネオノナン酸ビニル三元重合体、エチレン−酢酸ビニル−ネオデカン酸ビニル三元重合体;櫛状ポリマー、例えばフマル酸−酢酸ビニル共重合体;炭化水素ポリマー、例えば水素化ポリブタジエンポリマー、エチレン/1−アルケン共重合体、及びこれらに類似のポリマーを挙げることができる。同様に好適なものは、ワックス沈降防止剤(WASA)として当業者に知られている添加剤である。同様に好適なものは、EP0857776B1に記載されているようなアルキルフェノールホルムアルデヒド縮合物、又はEP−A−1482024に記載されているようなヒドロキシベンゾエートホルムアルデヒド縮合物等の縮合物分子種である。
以下の実施例は、本発明において使用されるポリマーの合成を説明する。同様の方法は、全ての他のポリマーを作成するために使用された。
フマル酸ジ−ドデシル(15.40g、34.01mmol)、酢酸ビニル(1.87g、21.72mmol)、及び454gmol-1の数平均分子量を有するポリ(エチレングリコールメチルエーテル)アクリレートエステル(3.27g、7.20mmol)を、シクロヘキサン(10ml)と共にシュレンク管に投入した。混合物を脱気して、窒素雰囲気下、撹拌しながら80℃にまで加熱した。tert−ブチルパーピバレート(tert-butyl perpivalate;0.1ml、シクロヘキサン中50質量%:50質量%)を添加し、重合を開始した。続く4時間の間、追加の開始剤を1時間毎に混合物に添加した。5時間が経過した時点で混合物を冷却し、生成物を得た。
以下の表1は、以下のモノマーを使用して調製されたポリマーの詳細を示す:
Claims (15)
- 式Iの構造単位、式IIの構造単位、及び式IIIa又は式IIIbのいずれかの構造単位を有し、かつ式VIIの構造単位を有していてもよいポリマー。
- R1及びR2が同一であり、それぞれ直鎖状のC12からC14のアルキル基を示す請求項1のポリマー。
- R3が−OCOR6を示す請求項1又は2のポリマー。
- R6がメチル基又は2−エチルヘキシル基であり、R4が水素原子である請求項3のポリマー。
- Xが式IVの基を示す請求項1から4のいずれかのポリマー。
- R7が水素原子、R8がメチル基、mが1から6の整数、nが6から18の整数である請求項5のポリマー。
- Xが式Vの基を示す請求項1から4のいずれかのポリマー。
- R9がC2アルキル架橋、R10及びR11が共にメチル基、及びqが0である請求項7のポリマー。
- Yが式IVの基を示し、式中、R7が水素原子、R8がメチル基、mが1から6の整数、及びnが6から18の整数である請求項1から8のいずれかのポリマー。
- 式VIIの構造単位を有する請求項1から9のいずれかのポリマー。
- R13が直鎖状のC12からC16のアルキル基を示す請求項10のポリマー。
- 多量の燃料油と、少量の、請求項1から11のいずれかのポリマーとを含む燃料油組成物。
- 燃料油が、動物性材料又は植物性材料から得られた油から調製される脂肪酸アルキルエステルを含む請求項12の燃料油組成物。
- 燃料油の低温特性を改善するための請求項1から11のいずれかのポリマーの使用。
- 請求項1から11のいずれかのポリマーと、それと相溶性の溶媒又は担体を含む添加剤濃縮物。
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CN102643690B (zh) * | 2012-04-26 | 2014-03-26 | 安徽大学 | 一种用于降低生物柴油凝固点的改进剂及其制备方法 |
US9145340B2 (en) | 2012-08-13 | 2015-09-29 | Verdesian Life Sciences, Llc | Method of reducing atmospheric ammonia in livestock and poultry containment facilities |
US9961922B2 (en) | 2012-10-15 | 2018-05-08 | Verdesian Life Sciences, Llc | Animal feed and/or water amendments for lowering ammonia concentrations in animal excrement |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60195193A (ja) * | 1984-02-21 | 1985-10-03 | エクソン リサーチ アンド エンヂニアリング コムパニー | 低温特性改良用添加剤を含有する蒸留燃料油 |
JPS61123698A (ja) * | 1984-11-15 | 1986-06-11 | エクソン リサーチ アンド エンヂニアリング コムパニー | 炭化水素に対する流れ向上剤ポリエステル |
JP2000212230A (ja) * | 1999-01-19 | 2000-08-02 | Clariant Gmbh | コポリマ―、及びこれを中間留分の低温流動性を向上するための添加剤として使用する方法 |
JP2003510409A (ja) * | 1999-09-21 | 2003-03-18 | エクソンモービル リサーチ アンド エンジニアリング カンパニー | エンジン油の低温走査ブルックフィールドゲル指数の低減 |
JP2006348297A (ja) * | 2005-06-15 | 2006-12-28 | Infineum Internatl Ltd | 排気煙生成が低減する低灰分又は無灰2サイクル潤滑油 |
JP2007262245A (ja) * | 2006-03-28 | 2007-10-11 | Sanyo Chem Ind Ltd | 流動点降下剤および炭化水素油組成物 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2233638C2 (de) * | 1972-07-08 | 1979-08-30 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur Herstellung stabiler wäßriger Polymerisatdispersionen des Vinylacetats mit Fumarsäureestern |
EP0156577B2 (en) * | 1984-03-22 | 1998-11-25 | Exxon Research And Engineering Company | Middle distillate compositions with improved cold flow properties |
CN1022044C (zh) * | 1984-03-22 | 1993-09-08 | 艾克森研究工程公司 | 改进低温流动性的中间馏分组合物 |
CN1022045C (zh) * | 1984-03-22 | 1993-09-08 | 艾克森研究工程公司 | 低温性质得到改进的中间馏分组合物 |
US4844168A (en) * | 1985-12-10 | 1989-07-04 | Marathon Oil Company | Delayed in situ crosslinking of acrylamide polymers for oil recovery applications in high-temperature formations |
CN1032221C (zh) | 1990-04-19 | 1996-07-03 | 埃克森化学专利公司 | 馏分燃料添加剂及含该添加剂的馏分燃料 |
ATE223953T1 (de) | 1997-01-07 | 2002-09-15 | Clariant Gmbh | Verbesserung der fliessfähigkeit von mineralölen und mineralöldestillaten unter verwendung von alkylphenol-aldehydharzen |
DE10058357B4 (de) * | 2000-11-24 | 2005-12-15 | Clariant Gmbh | Fettsäuremischungen verbesserter Kältestabilität, welche Kammpolymere enthalten, sowie deren Verwendung in Brennstoffölen |
EP1357168A1 (en) * | 2002-04-16 | 2003-10-29 | Infineum International Limited | Jet fuel compositions |
EP1482024B1 (en) | 2003-05-29 | 2010-12-08 | Infineum International Limited | A fuel oil composition |
EP1770150A1 (de) * | 2005-09-28 | 2007-04-04 | Basf Aktiengesellschaft | Turbinenkraftstoffzusammensetzungen mit verbesserten Kälteeigenschaften |
WO2009077396A1 (en) * | 2007-12-18 | 2009-06-25 | Basf Se | Biodiesel cold flow improver |
EP2664631B1 (en) * | 2008-07-31 | 2016-12-07 | The Lubrizol Corporation | Novel copolymers and lubricating compositions thereof |
-
2010
- 2010-09-30 AT AT10183171T patent/ATE542842T1/de active
- 2010-09-30 EP EP10183171A patent/EP2336206B1/en active Active
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60195193A (ja) * | 1984-02-21 | 1985-10-03 | エクソン リサーチ アンド エンヂニアリング コムパニー | 低温特性改良用添加剤を含有する蒸留燃料油 |
JPS61123698A (ja) * | 1984-11-15 | 1986-06-11 | エクソン リサーチ アンド エンヂニアリング コムパニー | 炭化水素に対する流れ向上剤ポリエステル |
JP2000212230A (ja) * | 1999-01-19 | 2000-08-02 | Clariant Gmbh | コポリマ―、及びこれを中間留分の低温流動性を向上するための添加剤として使用する方法 |
JP2003510409A (ja) * | 1999-09-21 | 2003-03-18 | エクソンモービル リサーチ アンド エンジニアリング カンパニー | エンジン油の低温走査ブルックフィールドゲル指数の低減 |
JP2006348297A (ja) * | 2005-06-15 | 2006-12-28 | Infineum Internatl Ltd | 排気煙生成が低減する低灰分又は無灰2サイクル潤滑油 |
JP2007262245A (ja) * | 2006-03-28 | 2007-10-11 | Sanyo Chem Ind Ltd | 流動点降下剤および炭化水素油組成物 |
Also Published As
Publication number | Publication date |
---|---|
KR20110073297A (ko) | 2011-06-29 |
CN102120804A (zh) | 2011-07-13 |
CA2726106C (en) | 2016-10-11 |
US20140144070A1 (en) | 2014-05-29 |
CA2726106A1 (en) | 2011-06-21 |
US20110146136A1 (en) | 2011-06-23 |
KR101811175B1 (ko) | 2017-12-20 |
JP5684560B2 (ja) | 2015-03-11 |
KR20170078579A (ko) | 2017-07-07 |
US20170073600A1 (en) | 2017-03-16 |
ATE542842T1 (de) | 2012-02-15 |
EP2336206A1 (en) | 2011-06-22 |
CN102120804B (zh) | 2014-10-29 |
EP2336206B1 (en) | 2012-01-25 |
US8710168B2 (en) | 2014-04-29 |
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