JP5150262B2 - Egr搭載ディーゼルエンジンの潤滑用の油組成物及び前記油組成物を有するegr搭載ディーゼルエンジン - Google Patents
Egr搭載ディーゼルエンジンの潤滑用の油組成物及び前記油組成物を有するegr搭載ディーゼルエンジン Download PDFInfo
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- JP5150262B2 JP5150262B2 JP2007547204A JP2007547204A JP5150262B2 JP 5150262 B2 JP5150262 B2 JP 5150262B2 JP 2007547204 A JP2007547204 A JP 2007547204A JP 2007547204 A JP2007547204 A JP 2007547204A JP 5150262 B2 JP5150262 B2 JP 5150262B2
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- 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
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 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
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 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
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[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
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 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
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 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
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 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
- ZAGXLQIHXTXRFW-UHFFFAOYSA-N tris(2-ethyl-4-methylhexyl)-tris(2-ethyl-4-methylhexyl)silyloxysilane Chemical compound CCC(C)CC(CC)C[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)O[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)CC(CC)CC(C)CC ZAGXLQIHXTXRFW-UHFFFAOYSA-N 0.000 description 1
- 229940057402 undecyl alcohol Drugs 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
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/26—Oils; Viscous liquids; Paints; Inks
- G01N33/28—Oils, i.e. hydrocarbon liquids
-
- 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
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—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 type
- C10M2209/084—Acrylate; Methacrylate
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—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 type
- C10M2209/086—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 type polycarboxylic, e.g. maleic acid
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
- C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
- C10N2030/041—Soot induced viscosity control
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Lubricants (AREA)
- Liquid Carbonaceous Fuels (AREA)
Description
a) C13〜C19−ポリアルキル(メタ)アクリラート(PAMA);
b) C7〜C12−PAMA(2−C1〜C4−基で分枝)、及び
c) 場合によりc1)C2〜C8−PAMA又はc2)ビニル芳香族化合物及び窒素含有ビニルモノマー(11個以下の炭素原子を有するエステル基<60%を有する)
を有する潤滑油組成物用の粘度向上剤を記載している。
(1a) 主要量の潤滑粘度の油を有する試料を得る工程;
(1b) 前記油の粘度を測定する工程;
(1c) 安定な試料/試料のペースト分散物及びカーボンブラックペーストを準備する工程;
(1d) 前記試料/ペースト分散物を平衡化させる工程;及び
(1e) 試料ペースト分散物の粘度を測定する工程、その際、剪断は前記工程(a)の後で常にエンジン環境の剪断効果を模倣するために加えられる
を有する、すすに関する粘度の増大を試験する方法を記載している。
a) C1〜C11−PAMAs 5〜75質量%;
b) C12〜C24−PAMAs 25〜95質量%;及び
c) N−分散剤 0.1〜20質量%
を有するコポリマーを記載している。
I) C6〜C15 10〜98mol%;Ib) C16〜C30−PAMA 0〜5mol%;c) C8〜C40−PAMA0〜90mol%;Id) C1〜C5−PAMA 0〜50mol%;及びIe) 酸素又は窒素分散剤PAMA 2〜20%;及び
II) IIa) C6〜C15 0〜90mol%;IIb) C16〜C30−PAMA 10〜70mol%;IIc) C8〜C40PAMA 0〜90mol%;IId) C1〜C5−PAMA 0〜50mol%;及びIIe) 酸素又は窒素分散剤PAMA 0〜20%を有する
ランダムPAMAコポリマーI/IIの二成分の組合せを記載している。
C1〜C24アルキル(メタ)アクリラート65〜95質量%;
スチレンモノマー5〜35質量%から誘導されたポリマー骨核92〜28%;及び
(専ら)C2〜C8−ヒドロキシアルキル(メタ)アクリラートから誘導された、前記骨核にグラフとする枝部2〜8%
を有するグラフトコポリマーを記載している。
a) C8〜C15−AMA 0〜80%;C16〜C28−AMA 20〜100%から誘導されるポリマー1 40〜75%及び
b) スチレン 25〜60%
を有するポリマーを記載している。
本発明の第1の態様の場合には、次の成分:
(i) 次のモノマー単位を有するポリマーの分散剤ブースター:
a) 式(I)
R1は、1〜5個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R2及びR3は、無関係に、H又は式−COOR′の基を表し、その際、R′はH又は1〜5個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 0〜40質量%、
b) 式(II)
R4は、6〜15個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R5及びR6は、無関係に、H又は式−COOR″の基を表し、その際、R″はH又は6〜15個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 10〜98質量%、
c) 式(III)
R7は、16〜30個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R8及びR9は、無関係に、H又は式−COOR″′の基を表し、その際、R″′はH又は16〜30個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 0〜30質量%、
d) ビニルモノマー 0〜30質量%、
e) 少なくとも1種のN−分散剤モノマー 7〜25質量%、
その際、a)〜e)は合計で100質量%になる;及び
(ii) 潤滑粘度の油
を有する潤滑粘度の油と、ポリマーの分散剤ブースターとを有する潤滑油組成物が提供される。
本発明の第3の態様の場合には、潤滑油組成物を有するディーゼルエンジンである。
本発明の第4の態様の場合には、EGRシステムを備えたディーゼルエンジンを潤滑する際の有効性について潤滑油組成物をスクリーニングする方法である。
(i) 次のモノマー単位を有するポリマーの分散剤ブースター:
a) 式(I)
R1は、1〜5個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R2及びR3は、無関係に、H又は式−COOR′の基を表し、その際、R′はH又は1〜5個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 0〜40質量%、
b) 式(II)
R4は、6〜15個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R5及びR6は、無関係に、H又は式−COOR″の基を表し、その際、R″はH又は6〜15個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 10〜98質量%、
c) 式(III)
R7は、16〜30個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R8及びR9は、無関係に、H又は式−COOR″′の基を表し、その際、R″′はH又は16〜30個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 0〜30質量%、
d) ビニルモノマー 5〜30質量%、
e) 少なくとも1種のN−分散剤モノマー 4〜25質量%、
その際、a)〜e)は合計で100質量%になる;及び
(ii) 潤滑粘度の油
を有する潤滑粘度の油と、ポリマーの分散剤ブースターとを有する潤滑油組成物である。
本発明の文脈の範囲内で、「アルキル(メタ)アクリラート」の用語は、アルキルアクリラートとアルキルメタクリラートの両方の種類又はその混合物を表す。
又は、
R13は、基NR18R19であり、その際、R18及びR19は4〜8員の飽和又は不飽和環の一部であり、前記環の一部は前記環の一部として少なくとも1個の炭素原子を有し、前記環の一部は酸素又は硫黄からなるグループから選択されるヘテロ原子に対する二重結合を形成し、その際、前記環は更にアルキル基又はアリール基で置換されていてもよい]のN−分散剤モノマーであることができる。
式
式
モノマーa) 0〜40質量%;
モノマーb) 10〜98質量%;
モノマーc) 0〜30質量%;
モノマーd) 5〜30質量%;及び
モノマーe) 4〜25質量%、
からなることができ、その際、a)〜e)は合計で100質量%になり、
その際、モノマーa)〜e)は前記されたものである。この実施態様の場合に、モノマーe)の量は、モノマーd)の存在を確保することにより減らすことができる。
約18〜31個のC原子を有するn−アルカン:0.7〜1.0%、
18〜31個のC原子を有する低分枝のアルカン:1.0〜8.0%、
14〜32個のC原子を有する芳香族化合物:0.4〜10.7%、
20〜32個のC原子を有するイソ−及びシクロアルカン:60.7〜82.4%、
極性化合物:0.1〜0.8%、
ロス:6.9〜19.4%。
グループI基本原料は、90%未満の飽和化合物及び/又は0.03%より多い硫黄を含有し、かつ表1中に特定された試験方法を用いて80以上及び120未満の粘度指数を有する。
基本材料の分析方法
特性 試験方法
飽和化合物 ASTM D 2007
粘度指数 ASTM D 2270
硫黄 ASTM D 2622
ASTM D 4294
ASTM D 4927
ASTM D 3120
前記基本原料の粘度指数は、粘度調整剤(VM)又は粘度指数向上剤(VII)として機能する特定のポリマー材料を組み込むことにより増加又は改善することができる。一般に、粘度調整剤として有用なポリマー材料は、約5000〜約250000、有利に約15000〜約200000、更に有利に約20000〜約150000の数平均分子量(Mn)を有するポリマー材料である。このような粘度調整剤は、グラフト材料、例えば無水マレイン酸でグラフトされていてもよく、このグラフトされた材料を、例えばアミン、アミド、窒素含有複素環化合物又はアルコールと反応させ、多官能性粘度調整剤を形成させることができる(分散剤−粘度調整剤)。
ポリマーの分散剤ブースターを含有する潤滑油の試料150mLを、CEC−L48−A−00に従って、160℃の温度で72時間、5L/hrの空気流量で酸化させた。カーボンブラック タイプS170(Degussa AG, Hanau-Wolfgang, Germany)を100℃で一晩中乾燥させた。酸化した油50gに、乾燥したカーボンブラック5質量%を、テフロンビーカー中で添加した。
すすに関連する粘度用の試料を試験する方法の場合に、主要量の潤滑粘度の油を有する試料を準備し、次いでこの試料の粘度を測定する。一般に、この試料の粘度測定は、逆流粘度計を含む通常の全ての粘度計を用いて標準的な実施により行われる。適当な粘度計は、SiI粘度計、Cannon- Fenske Routine粘度計、Cannon-Fenske Opaque粘度計及びZeitfuchs #4逆流粘度計を含む。主要量の潤滑粘度の油を有する前記試料は、例えば鉱油、合成油、例えば分散剤、酸化防止剤及び清浄剤を含有する完全調製油を含むことができる。
実施例1:20%DMAPMAmコポリマーの合成
ラウリルメタクリラート399gと、N−[3−(ジメチルアミノ)プロピル]メタクリルアミド100gと、セチル−エイコシルメタクリラート1gとのコモノマー混合物を、エルレンマイヤーフラスコ中に準備した。このコモノマー混合物に、1−ドデカンエチオール(Aldrich 98+%)連鎖移動剤4.5g、2,2′−アゾビス[2−メチルブチロニトリル](DuPont's VAZO 67)開始剤の25%溶液1.5gを2,6−ジメチル−4−ヘプタノン(Aldrich 90+%)中の25%溶液として添加した。前記混合物の30質量%(120g)を、凝縮器が取り付けられた、不活性ガスでパージした3リットルの四ツ口丸底フラスコに添加した。後チャージは、100N鉱油溶剤(SV100)75gの添加で完了した。一定の不活性ガスパージを維持して、前記混合物を撹拌し、95℃の反応温度にもたらした。反応温度で、残りのモノマー及び反応混合物を、一定の速度で90分間にわたりフラスコに添加し、95±5℃を維持するために必要な加熱及び冷却を交互に行った。この供給が完了した後に、この反応物を30分間95℃で維持した。この維持の後、更に2,6−ジメチル−4−ヘプタノンで25質量%溶液として溶解させた2,2′−アゾビス[2−メチルブチロニトリル]を含有する溶液5gを準備し、100N鉱油100gと混合した。この混合物を、一定の速度で90分間にわたり添加した。前記の供給の完了時に、この反応物を更に30分間95℃に維持した。この維持の完了時に、更に100N鉱油400gを添加し、完全に混合した。
例1の手順と同様の手順を10%DMAPMAmコポリマーの準備のために用いるが、ラウリルメタクリラートのチャージは449gであり、N−[3−(ジメチルアミノ)プロピル]メタクリルアミドのチャージは50gであった。
例1の手順と同様の手順を7%DMAPMAmコポリマーの準備のために用いるが、ラウリルメタクリラートのチャージは464gであり、N−[3−(ジメチルアミノ)プロピル]メタクリルアミドのチャージは35gであった。
実施例1の手順と同様の手順を20%DMAEMAコポリマーの準備のために用いるが、N−[3−(ジメチルアミノ)プロピル]メタクリルアミド100gの代わりにジメチルアミノエチルメタクリラート100gを使用した。
実施例1の手順と同様の手順を20%MEMAコポリマーの準備のために用いるが、N−[3−(ジメチルアミノ)プロピル]メタクリルアミド100gの代わりにモルホリノエチルメタクリラート100gを使用した。
実施例4aの手順と同様の手順を、6%DMAEMAコポリマーの準備のために用いるが、ラウリルメタクリラートのチャージは469gであり、DMAEMAのチャージは30gであった。
分枝したC12〜C15−アルコール混合物のメタクリル酸エステル 35.3g、
線状のC12〜C16−アルコール混合物のメタクリル酸エステル 17.5g、
線状のC12〜C20−アルコール混合物のメタクリル酸エステル0.3g、
N,N−ジメチルアミノエチルメタクリラート(DMAEMA) 1.7g
のコモノマー混合物をエルレンマイヤーフラスコ中に準備した。
実施例6の手順と同じ手順を使用したが、t−ブチルアミノエチルメタクリラートを、ジメチルアミノエチルメタクリラートの代わりに使用した。
実施例6の手順と同じ手順を使用したが、ジメチルアミノプロピルメタクリルアミド4.4gを、ジメチルアミノエチルメタクリラート1.7gの代わりに使用した。
実施例6の手順と同じ手順を使用したが、ジメチルアミノプロピルメタクリルアミドを、ジメチルアミノエチルメタクリラートの代わりに使用した。
実施例6の手順と同じ手順を使用したが、ジジメチルアミノエチルメタクリラートを使用しなかった。N−ビニルピロリジノンのチャージは3.9gであった。
分枝したC12〜C15−アルコール混合物のメタクリル酸エステル 31.8g、
線状のC12〜C16−アルコール混合物のメタクリル酸エステル 15.8g、
線状のC12〜C20−アルコール混合物のメタクリル酸エステル 0.3g、
スチレン 5.23g
のコモノマー混合物をエルレンマイヤーフラスコ中に準備した。
分枝したC12〜C15−アルコール混合物のメタクリル酸エステル 31.8g、
線状のC12〜C16−アルコール混合物のメタクリル酸エステル 15.8g、
線状のC12〜C20−アルコール混合物のメタクリル酸エステル 0.3g、
スチレン 5.23g、及び
ジメチルアミノプロピルメタクリルアミド 1.7g
のコモノマー混合物をエルレンマイヤーフラスコ中に準備した。
実施例12の手法と同様の手法を行うが、DMAEMAをDMAPMAmの代わりに使用した。
実施例12の手法と同様の手法を行うが、TBAEMAをDMAPMAmの代わりに使用した。
ViscoplexTM 8-702の市販の試料を使用した。
ViscoplexTM 6-054の市販の試料を使用した。
ViscoplexTM 6-954の市販の試料を使用した。
HitecTM 5777(分散剤オレフィンコポリマー)の市販の試料を使用した。
ヘビーデューティディーゼル油用の典型的な実施例として、15W40オイルを次の成分に従って調製した:
a) 高粘度油(例えばESSO 600 N)13〜18質量%;
b) 低粘度油(例えばESSO 150 N)61〜65質量%;
c) 典型的なDIパッケージ(例えばOloa 4595)10〜15質量%;
d) 非分散性VII(例えばOCP濃縮物)3〜8質量%;
e) 前記実施例に記載されたようなポリマーのN−分散剤ブースター(2〜8質量%、1〜4%活性成分に関連)。
1. 適当な粘度の潤滑油調製物を調製する。この粘度(ηi)をUbbelohde粘度計で測定する。
Claims (14)
- 潤滑油組成物を用いて排気ガス再循環システムを備えたディーゼルエンジンを潤滑することを有する前記エンジンの運転方法において、潤滑油組成物が
(i) 次のモノマー単位を有するポリマーの分散剤ブースター 0.5〜10質量%:
a) 式(I)
R1は、1〜5個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R2及びR3は、無関係に、H又は式−COOR′の基を表し、その際、R′はH又は1〜5個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 0〜40質量%、
b) 式(II)
R4は、6〜15個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R5及びR6は、無関係に、H又は式−COOR″の基を表し、その際、R″はH又は6〜15個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 10〜98質量%、
c) 式(III)
R7は、16〜30個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R8及びR9は、無関係に、H又は式−COOR″′の基を表し、その際、R″′はH又は16〜30個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 0〜30質量%、
d) ビニル芳香族モノマー 5〜30質量%、
e) ビニルピリジン、N−ビニルイミダゾール、N−ビニルピロリジノン(NVP)、モルホリノエチルメタクリラート、及びN−ビニルカプロラクタム、N,N−ジメチルアミノエチルメタクリラート(DMAEMA)、tert−ブチルアミノエチルメタクリラート、N,N−ジメチルアミノプロピルメタクリルアミド(DMAPMAM)、ジメチルアミノプロピルアクリルアミド、ジメチルアミノエチルアクリルアミドおよびビニル置換されたアミンからなる群から選択される少なくとも1種のN−分散剤モノマー 4〜25質量%、
その際、a)〜e)は合計で100質量%になる;及び
(ii) 潤滑粘度の油 70〜90質量%;及び更に:
非分散剤粘度向上剤 0.5〜15質量%;及び
清浄剤阻害剤パッケージ 0.5〜15質量%を有し、
その際、前記質量%値は合計で100質量%である、
を有する、排気ガス再循環システムを備えたディーゼルエンジンの運転方法。 - 前記のポリマーの分散剤ブースターが、前記油組成物の総質量に対して少なくとも1質量%の量で存在する、請求項1記載のディーゼルエンジンの運転方法。
- モノマーb)がC10〜C16−(メタ)アクリラートを有する、請求項1記載の方法。
- 前記ビニル芳香族モノマーは、スチレン及び置換スチレンからなるグループから選択された少なくとも1種である、請求項1記載の方法。
- 前記置換スチレンは、ハロゲン、アミノ、アルコキシ、カルボキシ、ヒドロキシ、スルホニル及びC1〜C12−ヒドロカルビルからなるグループから選択された置換基で置換されている、請求項4記載の方法。
- モノマーd) 5〜25質量%を有する、請求項1記載の方法。
- 前記N−分散剤モノマーが、ジメチルアミノプロピルメタクリルアミド、ジメチルアミノエチルメタクリルアミド、モルホリノエチルメタクリラート、及びtert−ブチルアミノエチルメタクリラートからなるグループから選択される少なくとも1種である、請求項1記載の方法。
- 前記N−分散剤モノマーは、N−ビニルピロリジノン、N,N−ジメチルアミノエチルメタクリラート、およびN,N−ジメチルアミノプロピルメタクリルアミドからなる群から選択される少なくとも1種のモノマーである、請求項1記載の方法。
- 前記N−分散剤モノマーがジメチルアミノプロピルメタクリルアミドである、請求項1記載の方法。
- 前記N−分散剤モノマーが8〜20質量%の量で存在する、請求項1記載の方法。
- 前記N−分散剤モノマーは、5質量%までの量でN−ビニルピロリジノンを有する、請求項1記載の方法。
- 前記ポリマーの分散剤ブースターは、50000〜500000の数平均分子量Mnを有する、請求項1記載の方法。
- 前記ポリマーの分散剤ブースターは、30サイクルKurt-Orbahn(Boschディーゼルインジェクター)試験により測定して、2〜55%の剪断安定性を有する、請求項1記載の方法。
- 潤滑油組成物を有する排気ガス再循環システムを備えたディーゼルエンジンにおいて、潤滑油組成物が次の成分:
(i) 次のモノマー単位を有するポリマーの分散剤ブースター 0.5〜10質量%:
a) 式(I)
R1は、1〜5個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R2及びR3は、無関係に、H又は式−COOR′の基を表し、その際、R′はH又は1〜5個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 0〜40質量%、
b) 式(II)
R4は、6〜15個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R5及びR6は、無関係に、H又は式−COOR″の基を表し、その際、R″はH又は6〜15個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 10〜98質量%、
c) 式(III)
R7は、16〜30個の炭素原子を有する線状又は分枝状のアルキル基を表し、
R8及びR9は、無関係に、H又は式−COOR″′の基を表し、その際、R″′はH又は16〜30個の炭素原子を有するアルキル基を表す]の1種又は数種のエチレン性不飽和エステル化合物 0〜30質量%、
d) ビニル芳香族モノマー 5〜30質量%、
e) ビニルピリジン、N−ビニルイミダゾール、N−ビニルピロリジノン(NVP)、モルホリノエチルメタクリラート、及びN−ビニルカプロラクタム、N,N−ジメチルアミノエチルメタクリラート(DMAEMA)、tert−ブチルアミノエチルメタクリラート、N,N−ジメチルアミノプロピルメタクリルアミド(DMAPMAM)、ジメチルアミノプロピルアクリルアミド、ジメチルアミノエチルアクリルアミドおよびビニル置換されたアミンからなる群から選択される少なくとも1種のN−分散剤モノマー 4〜25質量%、
その際、a)〜e)は合計で100質量%になる;及び
(ii) 潤滑粘度の油 70〜90質量%;及び更に:
非分散剤粘度向上剤 0.5〜15質量%;及び
清浄剤阻害剤パッケージ 0.5〜15質量%を有し、
その際、前記質量%値は合計で100質量%である、
を有する、排気ガス再循環システムを備えたディーゼルエンジン。
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MX (1) | MX2007007815A (ja) |
WO (1) | WO2006066649A2 (ja) |
Families Citing this family (21)
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DE10314776A1 (de) * | 2003-03-31 | 2004-10-14 | Rohmax Additives Gmbh | Schmierölzusammensetzung mit guten Reibeigenschaften |
DE102004021717A1 (de) * | 2004-04-30 | 2005-11-24 | Rohmax Additives Gmbh | Verfahren zur Herstellung von Schmierfett |
DE102004034618A1 (de) * | 2004-07-16 | 2006-02-16 | Rohmax Additives Gmbh | Verwendung von Pfropfcopolymeren |
DE102004037929A1 (de) * | 2004-08-04 | 2006-03-16 | Rohmax Additives Gmbh | Verfahren zur radikalischen Polymerisation ethylenisch-ungesättigter Verbindungen |
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 |
DE102006001771A1 (de) * | 2006-01-12 | 2007-07-19 | Röhm Gmbh | Verfahren zur Aufreinigung von (Meth)acrylaten |
DE102006039420A1 (de) | 2006-08-23 | 2008-02-28 | Evonik Rohmax Additves Gmbh | Verfahren zur Herstellung von Methacrylatestern |
KR20090025816A (ko) | 2007-09-07 | 2009-03-11 | 주식회사 동부하이텍 | 트렌치 트랜지스터 및 그의 형성 방법 |
EP2154230A1 (en) * | 2008-08-08 | 2010-02-17 | Afton Chemical Corporation | Lubricant additive compositions having improved viscosity index increasing properties |
ES2716233T3 (es) | 2009-08-07 | 2019-06-11 | Basf Se | Composición lubricante que comprende ácido alquil éter carboxílico |
US8802606B2 (en) | 2010-08-06 | 2014-08-12 | Basf Se | Lubricant composition having improved antiwear properties |
DE102010028195A1 (de) * | 2010-04-26 | 2011-10-27 | Evonik Rohmax Additives Gmbh | Schmiermittel für Getriebe |
DE102010038615A1 (de) * | 2010-07-29 | 2012-02-02 | Evonik Rohmax Additives Gmbh | Polyalkyl(meth)acrylat zur Verbesserung von Schmieröleigenschaften |
CN103249820A (zh) * | 2010-10-14 | 2013-08-14 | 赢创油品添加剂有限公司 | 具有改进性能的发动机 |
CN103201362A (zh) * | 2010-10-29 | 2013-07-10 | 赢创油品添加剂有限公司 | 具有改进的性能的柴油发动机 |
US8927469B2 (en) | 2011-08-11 | 2015-01-06 | Afton Chemical Corporation | Lubricant compositions containing a functionalized dispersant |
WO2014067749A1 (en) * | 2012-11-02 | 2014-05-08 | Evonik Industries Ag | Process for preparing low sulfur dispersant polymers |
WO2014067748A1 (en) | 2012-11-02 | 2014-05-08 | Evonik Industries Ag | Middle distillate formulations containing sulphur-free, dispersant alkylmethacrylate copolymers |
BR112017024047A2 (pt) * | 2015-05-22 | 2018-07-24 | Akzo Nobel Chemicals Int Bv | copolímero, pacote aditivo para combustíveis, método de preparação de copolímero, e uso de polímero ou pacote de aditivo |
SG11201810211XA (en) * | 2016-05-18 | 2018-12-28 | Evonik Oil Additives Gmbh | Antiwear copolymers and lubricant compositions |
US11359042B2 (en) | 2016-05-18 | 2022-06-14 | Evonik Operations Gmbh | Antiwear copolymers and lubricant compositions |
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NL123956C (ja) * | 1955-08-19 | |||
US4021357A (en) * | 1972-03-10 | 1977-05-03 | Texaco Inc. | Multifunctional tetrapolymer lube oil additive |
US3816315A (en) * | 1974-05-08 | 1974-06-11 | Texaco Inc | Mineral oil compositions |
US4557841A (en) * | 1984-11-13 | 1985-12-10 | Wynn Oil Company | Lubricant additive concentrate |
DE3930142A1 (de) * | 1989-09-09 | 1991-03-21 | Roehm Gmbh | Dispergierwirksame viskositaets-index-verbesserer |
US5571950A (en) * | 1994-04-28 | 1996-11-05 | Exxon Chemical Patents Inc. | Method for testing soot-related viscosity increase |
US5665685A (en) * | 1994-06-02 | 1997-09-09 | Sanyo Chemical Industries, Ltd. | Gear and transmission lubricant compositions of improved sludge-dispersibility, fluids comprising the same |
GB2355466A (en) * | 1999-10-19 | 2001-04-25 | Exxon Research Engineering Co | Lubricant Composition for Diesel Engines |
US6391996B1 (en) * | 1999-11-30 | 2002-05-21 | Rohmax Additives Gmbh | Copolymers obtainable by the ATRP method and a method for their preparation and their use |
US6715473B2 (en) * | 2002-07-30 | 2004-04-06 | Infineum International Ltd. | EGR equipped diesel engines and lubricating oil compositions |
JP4934844B2 (ja) * | 2002-06-07 | 2012-05-23 | 東燃ゼネラル石油株式会社 | 潤滑油組成物 |
US6869919B2 (en) * | 2002-09-10 | 2005-03-22 | Infineum International Ltd. | Lubricating oil compositions |
US20050124509A1 (en) * | 2003-12-04 | 2005-06-09 | Antonio Gutierrez | Lubricating oil compositions |
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 |
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2004
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- 2005-10-26 EP EP05798085.6A patent/EP1844127B1/en not_active Not-in-force
- 2005-10-26 WO PCT/EP2005/011453 patent/WO2006066649A2/en active Application Filing
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Publication number | Publication date |
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BRPI0519213A2 (pt) | 2009-01-06 |
JP2008525538A (ja) | 2008-07-17 |
US7560420B2 (en) | 2009-07-14 |
CA2586713A1 (en) | 2006-06-29 |
CA2586713C (en) | 2016-05-17 |
US20090270287A1 (en) | 2009-10-29 |
CN101061207B (zh) | 2013-08-14 |
WO2006066649A2 (en) | 2006-06-29 |
EP1844127B1 (en) | 2017-12-06 |
EP1844127A2 (en) | 2007-10-17 |
US20060142168A1 (en) | 2006-06-29 |
KR20070090948A (ko) | 2007-09-06 |
US8012919B2 (en) | 2011-09-06 |
WO2006066649A3 (en) | 2006-08-10 |
KR101473002B1 (ko) | 2014-12-15 |
CN101061207A (zh) | 2007-10-24 |
MX2007007815A (es) | 2007-07-24 |
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