JP5469237B2 - 硫黄含有化合物、金属化合物およびハロゲン化合物を含まず、かつ、残存モノマー量も少ない、低分子量の(メタ)アクリル系ポリマー、該(メタ)アクリル系ポリマーの製造方法、ならびに該(メタ)アクリル系ポリマーの使用 - Google Patents
硫黄含有化合物、金属化合物およびハロゲン化合物を含まず、かつ、残存モノマー量も少ない、低分子量の(メタ)アクリル系ポリマー、該(メタ)アクリル系ポリマーの製造方法、ならびに該(メタ)アクリル系ポリマーの使用 Download PDFInfo
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Description
(a)全体が少なくとも1種の(メタ)アクリル系モノマーのみで構成される開始材料を、単独でまたは任意で有機溶媒中の溶液の形態で、反応容器に投入し、この反応媒体を、好ましくは不活性雰囲気中で、例えば、窒素バブリングを行いながら、攪拌する工程;
(b)工程(a)に由来する開始材料を、重合温度に供する(昇温する)工程;
(c)前記重合温度で、ラジカル開始剤を、任意で有機溶媒中の溶液の形態で、継続的に添加する工程;
(d)工程(c)に由来する反応媒体を、数十分間のあいだ重合温度で保持する工程;
(e)前記反応媒体を50〜60℃の温度に冷却し、好ましくは酸化雰囲気中で、好ましくは攪拌しながら、少なくとも1種の重合禁止剤を添加する工程;および
(f)有機溶媒中の溶液の形態のポリマーを、好ましくは反応媒体中に存在する不純物をろ過除去してから、収集する工程。
−接触法およびビスブレーキング法に由来し、炭素数が18を超える重質パラフィンを高濃度で含む、最も重質な留分;
−フィッシャー=トロプシュ法などの気体変換法に由来する合成留分;
−植物由来および/または動物由来のバイオマスに対する、特に、NexBTL(Next Generation BTL)などの処理によって得られる、合成留分;
−植物油および/もしくは動物油、ならびに/または植物油および/もしくは動物油のエステル;
−動物由来および/または植物由来のバイオディーゼル;
などが挙げられる。
a)セタン価向上剤は、特に、硝酸アルキル、好ましくは硝酸2−エチルヘキシル、アロイルペルオキシド、好ましくはベンジルペルオキシド、およびアルキルペルオキシド、好ましくはtert−ブチルペルオキシドから選択される(しかし、必ずしもこれらに限定されない)。
b)消泡剤は、特に、ポリシロキサン、オキシアルキル化ポリシロキサン、および植物油または動物油から誘導された脂肪酸アミドから選択される(しかし、必ずしもこれらに限定されない)。消泡剤の例は、欧州特許第861882号明細書、欧州特許第663000号明細書、欧州特許第736590号明細書などに記載されている。
c)清浄剤および/または腐食防止剤は、特に、アミン類、スクシンイミド、アルケニルスクシンイミド、ポリアルキルアミン、ポリアルキルポリアミン、およびポリエーテルアミンから選択される(しかし、必ずしもこれらに限定されない)。清浄剤および/または腐食防止剤の例は、欧州特許第938535号明細書などに記載されている。
d)油性向上剤または減摩耗剤は、特に、脂肪酸、および脂肪酸のエステル誘導体またはアミド誘導体から選択され、特には、モノオレイン酸グリセロール、モノカルボン酸または多環式カルボン酸の誘導体である(しかし、必ずしもこれらに限定されない)。油性向上剤または減摩耗剤の例は、欧州特許第680506号明細書、欧州特許第860494号明細書、国際公開第98/04656号パンフレット、欧州特許第915944号明細書、仏国特許出願公開第2772783号明細書、仏国特許発明第2772784号明細書などに記載されている。
e)曇り点降下剤は、特に、長鎖オレフィン類/(メタ)アクリルエステル/マレイミドのターポリマー、およびフマル酸/マレイン酸のエステルのポリマーからなる群から選択される(しかし、必ずしもこれらに限定されない)。曇り点降下剤の例は、欧州特許第0071513号明細書、欧州特許第100248号明細書、仏国特許発明第2528051号明細書、仏国特許発明第2528051号明細書、仏国特許発明第2528423号明細書、欧州特許第112195号明細書、欧州特許第172758号明細書、欧州特許第271385号明細書、欧州特許第291367号明細書などに記載されている。
f)堆積防止剤および/またはパラフィン分散剤は、特に、(メタ)アクリル酸/ポリアミンアミド化(polyamine amidified)(メタ)アクリル酸アルキルのコポリマー、ポリアミンアルケニルスクシンイミド、フタルアミド酸と二鎖型脂肪アミンとの誘導体、およびアルキルフェノール樹脂からなる群から選択される(しかし、必ずしもこれらに限定されない)。堆積防止剤および/またはパラフィン分散剤の例は、欧州特許第261959号明細書、欧州特許第593331号明細書、欧州特許第674689号明細書、欧州特許第327423号明細書、欧州特許出願公開第512889号明細書、欧州特許第832172号明細書、米国特許出願公開第2005/0223631号明細書、米国特許第5998530号明細書、国際公開第93/14178号パンフレットなどに記載されている。
g)多数の官能基を有する低温動作性添加剤は、欧州特許第573490号明細書に記載されているような硝酸アルケニルとオレフィンとのコポリマーからなる群から選択される。
h)防腐・防かび剤。
i)導電性向上剤。
j)燃焼向上剤
k)消臭剤。
−細管粘度計(Walter Herzog社製)を用いて、NF EN ISO 3104規格に準拠して測定される40℃での動粘度(mm2/s);
−Waters社製の参照カラムを5個(HR4+3+2+1+0.5)直列接続したものを備えたWaters社製のクロマトグラフと、溶出液としてのTHFとを用いたゲル浸透クロマトグラフィー(GPC)によって測定される、PMMA(ポリ(メタクリル酸メチル))当量で表される重量平均分子量(Mw)(g/モル);サンプルは、THFで0.5%に希釈したものを調製し、毎分1mlの溶出速度で溶出され、屈折率測定法によって検出される;
−ゲル浸透クロマトグラフィー(GPC)によって測定される残存モノマー量;
−NF EN 116規格に準拠して測定されるフィルター通過可能限界温度(LFT);
−NF T 60 105規格に準拠して測定される流動点(PP);
−NF EN 23 015規格に準拠して測定される曇り点(CP);
−IP391規格に準拠して測定される芳香族分量;
−DSCを用いて測定される結晶化開始温度(COT);
−D 86規格に準拠して測定される蒸留温度;
−ASTM D4737規格に準拠して測定されるセタン価;
−NF EN ISO 12185規格に準拠して測定される40℃での密度(D40)および15℃での密度(D15)。
−アクリル酸C18〜C22アルキル(融点:40℃;分子量:352g/モル)(Arkema France社製;商品名:Norsocryl(登録商標)A18〜22);
−アクリル酸ベヘニル(C22)を42〜46重量%、アクリル酸C18アルキルを40〜44重量%、アクリル酸C20アルキルを9〜13重量%、アクリル酸C16−アルキルを1.5重量%以下、およびアクリル酸C22+アルキルを2重量%以下含む、アクリル酸C18〜C22アルキル(Cognis社製;商品名:45%Benhenyl Acrylate);
−ペルオキシ安息香酸tert−ブチル(Arkema France社製;商品名:LUPEROX(登録商標)P);
−ペルオキシ−2−エチルヘキサン酸tert−ブチル(Arkema France社製;商品名:LUPEROX(登録商標)26);
−分解促進剤:N,N’−ジメチル−p−トルイジン(NNDPT)(Akzo Nobel社製;商品名:Accelerator(登録商標)NL−65−100、あるいは、Cognis社製;商品名:Bisomer(登録商標)PTE);
−有機溶媒:芳香族溶媒(Exxon Mobil社製;商品名:Solvesso 150(S150));
− 重合禁止剤:モノメチルエーテルヒドロキノン(MMEHQ)。
予め窒素を用いて脱気されて窒素雰囲気下に置かれた200Lの重合反応容器に対し、70℃のオーブンで予め溶融された45%Benhenyl Acrylate(294.7重量部)とSolvesso 150(631.2重量部)とで構成される開始材料を投入した。この開始材料に対して、少量の窒素バブリング(1m3/時)および攪拌(U字アンカー型攪拌翼;攪拌速度:75rpm)を行った後、100℃に昇温した。
ラジカル開始剤と分解促進剤(NNDPT)とを併用した以外は実施例1と同様に行った。分解促進剤(4重量部)を、開始剤の有機溶液と同時に、継続的に添加した。
ペルオキシ安息香酸tert−ブチルを、同一のモル比でペルオキシ−2−エチルヘキサン酸tert−ブチルに置き換えた以外は実施例1と同様に行った。
ラジカル開始剤と分解促進剤(NNDPT)とを併用した以外は実施例3と同様に行った。分解促進剤(4重量部)を、開始剤の有機溶液と同時に、継続的に添加した。
予め窒素を用いて脱気されて窒素雰囲気下に置かれた重合反応容器に対し、Solvesso 150(75重量部)とLUPEROX(登録商標)26(4重量部)とで構成される開始材料を投入した。この開始材料を、攪拌(U字アンカー型攪拌翼)しながら、100℃に昇温した。
この実施例では、実施例1〜6のポリマーB1〜B6を家庭用燃料油に添加した際の、当該ポリマーによるLFT(フィルター通過可能限界温度)の改善効果を測定・比較した。フィルター通過性添加剤(LFT添加剤)およびフィルター通過効果増強剤のいずれも配合していない状態での、試験対象となる留分の特性を、以下の表2にまとめる。
この実施例では、実施例1〜6のポリマーB1〜B6をディーゼル内燃機関燃料油に添加した際の、当該ポリマーによるLFT(フィルター通過可能限界温度)の改善効果を測定・比較した。フィルター通過性添加剤(LFT添加剤)および効果増強剤のいずれも配合していない状態での、試験対象となる留分の特性を、以下の表4にまとめる。
Claims (11)
- 直鎖状または分岐鎖状の脂肪鎖を有する(メタ)アクリル系化合物による、(メタ)アクリル系ポリマーであって、前記脂肪鎖は、炭素数C8以上で、任意で少なくとも1つのエチレン不飽和部を含むものであり、当該(メタ)アクリル系ポリマーは、重量平均分子量Mwが20,000g/モル未満であり、硫黄含有化合物、金属化合物およびハロゲン化合物を含まない(メタ)アクリル系ポリマーを、溶液中でラジカル重合によって製造する方法において、
(a)全体が少なくとも1種の(メタ)アクリル系モノマーのみで構成される開始材料を、単独でまたは任意で有機溶媒中の溶液の形態で、反応容器に投入し、この反応媒体を攪拌する工程と、
(b)工程(a)に由来する開始材料を、重合温度に昇温する工程と、
(c)前記重合温度で、ラジカル開始剤を、任意で有機溶媒中の溶液の形態で、継続的に添加する工程と、
(d)工程(c)に由来する反応媒体を、数十分間のあいだ重合温度で保持する工程と、
(e)前記反応媒体を50〜60℃の温度に冷却し、少なくとも1種の重合禁止剤を添加する工程と、
(f)有機溶媒中の溶液の形態のポリマーを、収集する工程と、
を含むことを特徴とする、(メタ)アクリル系ポリマーの製造方法。 - 請求項1において、(メタ)アクリル系モノマーが、炭素数12〜50の直鎖または分岐鎖を有することを特徴とする、(メタ)アクリル系ポリマーの製造方法。
- 請求項1または2において、ラジカル開始剤の量が、モノマーに対して2〜14重量%であることを特徴とする、(メタ)アクリル系ポリマーの製造方法。
- 請求項1から3のいずれか一項において、ラジカル開始剤が、有機ペルオキシド化合物であることを特徴とする、(メタ)アクリル系ポリマーの製造方法。
- 請求項1から4のいずれか一項において、有機溶媒中の溶液の形態の分解促進剤が、ラジカル開始剤と併用され、当該開始剤と同時または別々に反応媒体に投入されることを特徴とする、(メタ)アクリル系ポリマーの製造方法。
- 請求項5において、分解促進剤が、芳香族アミン誘導体であることを特徴とする、(メタ)アクリル系ポリマーの製造方法。
- 請求項1から6のいずれか一項において、(メタ)アクリル系ポリマーの、GPCによって測定される残存モノマー量が、10重量%以下である、(メタ)アクリル系ポリマーの製造方法。
- 請求項1から7のいずれか一項に記載の方法により得られる(メタ)アクリル系ポリマーの、高固形分の溶媒和性アクリル樹脂の処方物に配合される添加剤としての使用。
- 請求項1から7のいずれか一項に記載の方法により得られる(メタ)アクリル系ポリマーの、油系処方物に配合される添加剤としての使用。
- 請求項9において、油系処方物が、潤滑剤処方物、燃料処方物、または可燃性処方物である使用。
- 請求項9または10において、沸点150〜450℃の炭化水素系留分中で、当該留分に添加される、エチレンとC3〜C5カルボン酸のビニルエステルと炭素数1〜10のモノアルコールとのコポリマーおよび/またはターポリマーを含むフィルター通過性添加剤の効果を増強する使用。
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PCT/FR2010/050544 WO2010109144A1 (fr) | 2009-03-25 | 2010-03-25 | Polymeres (meth) acryliques de bas poids moleculaire, exempts de composes soufres, metalliques et halogenes et de taux de monomeres residuels faible, leur procede de preparation et leurs utilisations |
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Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2969620B1 (fr) | 2010-12-23 | 2013-01-11 | Total Raffinage Marketing | Resines alkylphenol-aldehyde modifiees, leur utilisation comme additifs ameliorant les proprietes a froid de carburants et combustibles hydrocarbones liquides |
FR2974111B1 (fr) | 2011-04-14 | 2013-05-10 | Total Raffinage Marketing | Lubrifiant cylindre pour moteur marin deux temps |
FR2992655B1 (fr) | 2012-06-29 | 2015-07-31 | Total Raffinage Marketing | Composition lubrifiante |
US9957342B2 (en) * | 2012-11-02 | 2018-05-01 | Evonik Oil Additives Gmbh | Process for preparing low sulfur dispersant polymers |
CN104837872B (zh) * | 2012-12-18 | 2017-08-08 | 巴斯夫欧洲公司 | 乙烯‑乙烯基酯共聚物和(甲基)丙烯酸烷基酯构成的聚合物组合物,其制备方法及其作为原油、矿物油或矿物油产品的倾点下降剂的用途 |
FR3005061B1 (fr) | 2013-04-25 | 2016-05-06 | Total Raffinage Marketing | Additif pour ameliorer la stabilite a l'oxydation et/ou au stockage de carburants ou combustibles hydrocarbones liquides |
FR3005474B1 (fr) | 2013-05-07 | 2016-09-09 | Total Raffinage Marketing | Lubrifiant pour moteur marin |
JP6752793B2 (ja) * | 2014-12-18 | 2020-09-09 | エボニック オペレーションズ ゲーエムベーハー | アルキルメタクリレートと無水マレイン酸とのコポリマーの製造方法 |
JP2017032918A (ja) * | 2015-08-05 | 2017-02-09 | Jsr株式会社 | 硬化膜形成用組成物、硬化膜、発光表示素子、フィルム及び硬化膜の形成方法 |
CN109642137A (zh) | 2016-07-06 | 2019-04-16 | 伊士曼化工公司 | (甲基)丙烯酸系低聚物 |
WO2018155989A1 (ko) | 2017-02-27 | 2018-08-30 | 주식회사 엘지화학 | 아크릴계 점착제의 제조 방법 및 이로부터 제조된 점착 필름 |
RU2735083C2 (ru) * | 2019-04-26 | 2020-10-28 | Андрей Вячеславович Аристов | Топливная композиция дизельного топлива |
Family Cites Families (68)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3028367A (en) | 1958-04-14 | 1962-04-03 | Rohm & Haas | Copolymers of hydroxyalkyl acrylates and methacrylates and alkyl acrylates and methacrylates reacted with diisocyanates |
US3627838A (en) | 1964-12-11 | 1971-12-14 | Exxon Research Engineering Co | Process for manufacturing potent pour depressants |
US4056559A (en) * | 1971-04-23 | 1977-11-01 | Rohm And Haas Company | Novel polymers of alkyl methacrylates |
US4117235A (en) | 1971-09-23 | 1978-09-26 | Owens-Illinois, Inc. | Novel preparation of novel low molecular weight, liquid polymer |
DE2757329C2 (de) | 1977-12-22 | 1980-02-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Polymerisaten der Acrylsäure oder Methacrylsäure |
DE2960183D1 (en) | 1978-07-26 | 1981-04-02 | Basf Ag | Middle distillates of petroleum, suitable as diesel fuel or as light heating oil, and with improved filtration properties |
SE449493B (sv) | 1979-12-13 | 1987-05-04 | Inst Francais Du Petrole | Sampolymer av en akrylsyraester, en dikarboxiforening och diisobuten, samt dess anvendning som flytegenskapsforbettrande tillsatsmedel i kolveteoljor |
FR2471390A1 (fr) * | 1979-12-13 | 1981-06-19 | Inst Francais Du Petrole | Terpolymeres utilisables notamment comme additifs pour ameliorer les proprietes d'ecoulement des huiles lubrifiantes |
FR2510598A1 (fr) | 1981-07-30 | 1983-02-04 | Inst Francais Du Petrole | Utilisation d'additifs azotes comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs |
FR2528066A1 (fr) | 1982-06-04 | 1983-12-09 | Inst Francais Du Petrole | Additifs azotes utilisables comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs |
FR2528051B1 (fr) | 1982-06-08 | 1986-05-02 | Inst Francais Du Petrole | Additifs azotes utilisables comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs |
FR2528423B1 (fr) | 1982-06-10 | 1987-07-24 | Inst Francais Du Petrole | Additifs azotes utilisables comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs |
FR2535723A1 (fr) | 1982-11-09 | 1984-05-11 | Inst Francais Du Petrole | Additifs azotes utilisables comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs |
FR2567536B1 (fr) | 1984-07-10 | 1986-12-26 | Inst Francais Du Petrole | Compositions d'additifs destinees notamment a ameliorer les proprietes de filtrabilite a froid des distillats moyens de petrole |
US4652605A (en) | 1984-12-17 | 1987-03-24 | Ppg Industries, Inc. | Preparation of low molecular weight polymers by vinyl addition polymerization under dilute reaction conditions using a polymeric diluent |
EP0261959B1 (en) | 1986-09-24 | 1995-07-12 | Exxon Chemical Patents Inc. | Improved fuel additives |
FR2604712B1 (fr) | 1986-10-02 | 1988-12-30 | Inst Francais Du Petrole | Copolymere acrylate acrylamide a bas poids moleculaire et procede pour empecher au moins en partie la formation de depot de sels issus de milieux aqueux |
FR2607139B1 (fr) | 1986-11-21 | 1989-08-18 | Inst Francais Du Petrole | Polymeres a fonctions azotees derives de polyesters insatures et leur utilisation comme additifs d'abaissement du point d'ecoulement des distillats moyens d'hydrocarbures |
FR2613371B1 (fr) | 1987-04-01 | 1989-07-07 | Inst Francais Du Petrole | Copolymeres azotes, leur preparation et leur utilisation comme additifs pour ameliorer les proprietes d'ecoulement des distillats moyens d'hydrocarbures |
FR2626578B1 (fr) | 1988-02-03 | 1992-02-21 | Inst Francais Du Petrole | Polymeres amino-substitues et leur utilisation comme additifs de modification des proprietes a froid de distillats moyens d'hydrocarbures |
GB9104138D0 (en) | 1991-02-27 | 1991-04-17 | Exxon Chemical Patents Inc | Polymeric additives |
FR2676062B1 (fr) | 1991-05-02 | 1993-08-20 | Inst Francais Du Petrole | Polymere amino-substitues et leur utilisation comme additifs de modification des proprietes a froid de distillats moyens d'hydrocarbures. |
GB9200694D0 (en) | 1992-01-14 | 1992-03-11 | Exxon Chemical Patents Inc | Additives and fuel compositions |
DE69333752T3 (de) * | 1992-06-10 | 2011-03-03 | Nippon Shokubai Co. Ltd. | Verfahren zur Herstellung eines hydrophilen Harzes |
GB9219962D0 (en) | 1992-09-22 | 1992-11-04 | Exxon Chemical Patents Inc | Additives for organic liquids |
ES2103066T3 (es) | 1992-10-09 | 1997-08-16 | Inst Francais Du Petrole | Fosfatos de aminas que incluyen un ciclo imida terminal, su preparacion y su utilizacion como aditivos para carburantes motores. |
FR2699550B1 (fr) | 1992-12-17 | 1995-01-27 | Inst Francais Du Petrole | Composition de distillat moyen de pétrole contenant des additifs azotés utilisables comme agents limitant la vitesse de sédimentation des paraffines. |
JP2673646B2 (ja) | 1993-01-19 | 1997-11-05 | 三洋化成工業株式会社 | 顔料分散樹脂用ビニル系重合体の製造法 |
GB9301119D0 (en) | 1993-01-21 | 1993-03-10 | Exxon Chemical Patents Inc | Fuel composition |
DE69415095T2 (de) * | 1993-07-27 | 1999-05-20 | Shell Int Research | Polymere fliessverbesserte Zusätze |
US5475073A (en) * | 1994-11-18 | 1995-12-12 | Arco Chemical Technology, L.P. | Hydroxy-functional acrylate resins |
FR2735494B1 (fr) | 1995-06-13 | 1997-10-10 | Elf Antar France | Additif bifonctionnel de tenue a froid et composition de carburant |
FR2751982B1 (fr) | 1996-07-31 | 2000-03-03 | Elf Antar France | Additif d'onctuosite pour carburant moteurs et composition de carburants |
FR2753455B1 (fr) | 1996-09-18 | 1998-12-24 | Elf Antar France | Additif detergent et anti-corrosion pour carburants et composition de carburants |
DE59708189D1 (de) | 1997-01-07 | 2002-10-17 | Clariant Gmbh | Verbesserung der Fliessfähigkeit von Mineralölen und Mineralöldestillaten unter Verwendung von Alkylphenol-Aldehydharzen |
US5730029A (en) | 1997-02-26 | 1998-03-24 | The Lubrizol Corporation | Esters derived from vegetable oils used as additives for fuels |
JPH10237467A (ja) | 1997-02-26 | 1998-09-08 | Tonen Corp | ディーゼルエンジン用燃料油組成物 |
AU1278199A (en) * | 1997-10-31 | 1999-05-24 | Cognis Corporation | Continuous bulk polymerization process |
DE19752127A1 (de) * | 1997-11-25 | 1999-07-29 | Stockhausen Chem Fab Gmbh | Verfahren zur Herstellung von synthetischen Polymerisaten mit sehr niedrigem Restmonomergehalt, danach hergestellte Produkte und deren Verwendung |
DE19754555A1 (de) | 1997-12-09 | 1999-06-24 | Clariant Gmbh | Verfahren zur Herstellung von Ethylen-Mischpolymerisaten und deren Verwendung als Zusatz zu Mineralöl und Mineralöldestillaten |
FR2772784B1 (fr) | 1997-12-24 | 2004-09-10 | Elf Antar France | Additif d'onctuosite pour carburant |
FR2772783A1 (fr) | 1997-12-24 | 1999-06-25 | Elf Antar France | Additif d'onctuosite pour carburant |
CA2364554C (fr) * | 1999-03-31 | 2010-09-14 | Cray Valley Sa | Compositions de resines thermodurcissables comprenant des microparticules reticulees reactives de tenue mecanique amelioree |
US6927268B2 (en) * | 2000-06-21 | 2005-08-09 | Nippon Shokubai Co., Ltd. | Production process for water-absorbent resin |
US6844406B2 (en) | 2000-10-04 | 2005-01-18 | Valspar Sourcing, Inc. | High functionality number, low molecular weight polymers and methods of making same |
US7629428B2 (en) * | 2004-01-28 | 2009-12-08 | Basf Aktiengesellschaft | Method for producing polymers |
EP1564229A1 (en) | 2004-02-13 | 2005-08-17 | Total Petrochemicals Research Feluy | Olefin polymerization process in the presence of an anti-fouling agent |
US20050223631A1 (en) | 2004-04-07 | 2005-10-13 | Graham Jackson | Fuel oil compositions |
DE102004037929A1 (de) * | 2004-08-04 | 2006-03-16 | Rohmax Additives Gmbh | Verfahren zur radikalischen Polymerisation ethylenisch-ungesättigter Verbindungen |
DE102005004285A1 (de) * | 2005-01-28 | 2006-08-03 | Stockhausen Gmbh | Wasserlösliche oder wasserquellbare Polymerisate, insbesondere wasserlösliche oder wasserquellbare Copolymere aus Acrylamid und mindestens einem ionischen Comonomeren mit niedrigem Restmonomerengehalt |
US7648950B2 (en) * | 2005-04-22 | 2010-01-19 | Rohmax Additives Gmbh | Use of a polyalkylmethacrylate polymer |
DE102005041528A1 (de) * | 2005-08-31 | 2007-03-01 | Rohmax Additives Gmbh | Öllösliche Polymere |
EP2004700B1 (de) * | 2006-03-31 | 2013-03-13 | Basf Se | Verfahren zur herstellung von acrylatcopolymeren |
US9149564B2 (en) * | 2006-06-23 | 2015-10-06 | The Regents Of The University Of California | Articles comprising large-surface-area bio-compatible materials and methods for making and using them |
FR2903418B1 (fr) * | 2006-07-10 | 2012-09-28 | Total France | Utilisation de composes revelateurs d'efficacite des additifs de filtrabilite dans des distillats hydrocarbones, et composition synergique les contenant. |
FR2903410A1 (fr) * | 2006-07-10 | 2008-01-11 | Arkema France | Polymeres (meth)acryliques de bas poids moleculaires et exempts de composes soufres, metalliques et halogenes, leur procede de preparation et leur utilisation |
FR2903607A1 (fr) * | 2006-07-12 | 2008-01-18 | Christophe Bastid | Dispositif medical intra-buccal |
US20080016181A1 (en) * | 2006-07-13 | 2008-01-17 | Erik John Burckart | Method and system for providing remote media |
DE102006034893A1 (de) * | 2006-07-25 | 2008-01-31 | Tesa Ag | Bimodale Acrylathaftklebemasse zur Verklebung von niederenergetischen und rauhen Oberflächen |
FR2911611B1 (fr) | 2007-01-23 | 2011-01-07 | Total France | Composition bitumineuse aux proprietes thermoreversibles. |
FR2919298B1 (fr) | 2007-07-24 | 2012-06-08 | Total France | Composition bitume/polymere a reticulation thermoreversible. |
FR2919294B1 (fr) | 2007-07-24 | 2012-11-16 | Total France | Polymere greffe et composition de bitume a reticulation thermoreversible comprenant ledit polymere greffe. |
FR2919293B1 (fr) | 2007-07-27 | 2009-11-06 | Total France Sa | Polymeres d'ethylene et d'esters vinyliques modifies par greffage,leur procede de preparation et leur application en tant qu'additifs ameliorant les proprietes a froid des hydrocarbures liquides |
EP2050755A1 (en) | 2007-10-19 | 2009-04-22 | Total Petrochemicals Research Feluy | Supported ionic liquids or activating supports |
FR2924121A1 (fr) | 2007-11-27 | 2009-05-29 | Total France Sa | Composition bitumineuse elastique reticulee de maniere thermoreversible |
FR2925909B1 (fr) | 2007-12-26 | 2010-09-17 | Total France | Additifs bifonctionnels pour hydrocarbures liquides obtenus par greffage a partir de copolymeres d'ethylene et/ou de propylene et d'esters vinyliques |
JP5403219B2 (ja) * | 2008-03-31 | 2014-01-29 | 荒川化学工業株式会社 | 活性エネルギー線硬化型ウェットオフセット印刷インキ |
FR2936812B1 (fr) | 2008-10-03 | 2010-10-15 | Total France | Compositions lubrifiantes pour transmissions. |
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- 2010-03-25 MX MX2011010048A patent/MX337522B/es active IP Right Grant
- 2010-03-25 EA EA201171161A patent/EA023072B1/ru not_active IP Right Cessation
- 2010-03-25 KR KR20117025198A patent/KR20120002597A/ko not_active Application Discontinuation
- 2010-03-25 CN CN201080018412.8A patent/CN102414225B/zh not_active Expired - Fee Related
- 2010-03-25 WO PCT/FR2010/050544 patent/WO2010109144A1/fr active Application Filing
- 2010-03-25 SG SG2011069291A patent/SG174911A1/en unknown
- 2010-03-25 UA UAA201112543A patent/UA105789C2/uk unknown
- 2010-03-25 EP EP10716577.1A patent/EP2411419B1/fr active Active
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Also Published As
Publication number | Publication date |
---|---|
CA2756415C (fr) | 2017-01-03 |
EP2411419B1 (fr) | 2018-05-02 |
UA105789C2 (uk) | 2014-06-25 |
MY155828A (en) | 2015-12-15 |
US20120077721A1 (en) | 2012-03-29 |
SG174911A1 (en) | 2011-11-28 |
CN102414225B (zh) | 2014-10-22 |
MX337522B (es) | 2016-03-09 |
CN102414225A (zh) | 2012-04-11 |
KR20120002597A (ko) | 2012-01-06 |
EA023072B1 (ru) | 2016-04-29 |
AU2010227355A1 (en) | 2011-10-13 |
BRPI1006488A2 (pt) | 2018-03-27 |
US9102767B2 (en) | 2015-08-11 |
WO2010109144A1 (fr) | 2010-09-30 |
CA2756415A1 (fr) | 2010-09-30 |
FR2943678A1 (fr) | 2010-10-01 |
AU2010227355B2 (en) | 2015-10-29 |
ZA201106868B (en) | 2012-03-28 |
JP2012521473A (ja) | 2012-09-13 |
FR2943678B1 (fr) | 2011-06-03 |
EA201171161A1 (ru) | 2012-03-30 |
EP2411419A1 (fr) | 2012-02-01 |
MX2011010048A (es) | 2012-02-08 |
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