CN1094507C - 由支链羰基合成酸制备的可生物降解的合成酯基料 - Google Patents
由支链羰基合成酸制备的可生物降解的合成酯基料 Download PDFInfo
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- CN1094507C CN1094507C CN97194836A CN97194836A CN1094507C CN 1094507 C CN1094507 C CN 1094507C CN 97194836 A CN97194836 A CN 97194836A CN 97194836 A CN97194836 A CN 97194836A CN 1094507 C CN1094507 C CN 1094507C
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- acid
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- lubricant
- additive
- agent
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- 238000012360 testing method Methods 0.000 claims abstract description 42
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- 239000002904 solvent Substances 0.000 claims abstract description 14
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims abstract description 13
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- MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 claims description 3
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- OJTHHBCWUMTZEY-UHFFFAOYSA-N 5-methyl-heptanoic acid Chemical compound CCC(C)CCCC(O)=O OJTHHBCWUMTZEY-UHFFFAOYSA-N 0.000 claims 1
- 241001074085 Scophthalmus aquosus Species 0.000 claims 1
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Abstract
一种从约60-99wt%至少一种可生物降解的合成酯基料、约1-20wt%润滑剂添加剂组合和0-20%溶剂制备的可生物降解的润滑剂，所述的可生物降解的合成酯基料包括支链醇或直链醇和至少一种支链羰基合成酸的反应产品，所述的支链醇或直链醇的通式为R(OH)n，其中R是含有约2-20碳原子的脂族或环脂族基和n至少为2；所述的支链羰基合成酸含有碳原子数在约C5-C10的范围内，条件是这种支链羰基合成酸不包括2-乙基己酸；其中酯基料呈现出如下的性能：用改进的Sturm试验测定在28天内至少60%的生物降解性，倾点低于-25℃，在-25℃黏度低于7500厘泊。
Description
本发明一般涉及为改进可生物降解润滑剂的基料的冷流性能和分散剂溶解性能而不损失生物降解作用或润滑作用的支链合成酯的应用。通过用支链羰基合成酸酯化多羟基化合物(例如三羟甲基丙烷(TMP)或新戊二醇(NPG))可实现至少60％的生物降解性(用改进的Sturm试验测量)，前提是2-乙基己酸不包括在所述羰基合成酸中。这些支链的合成酯特别适用于形成双冲程发动机油，弹射器油，液压流体，钻孔流体，水轮机油，齿轮油，润滑脂，压缩机油和其它工业和发动机在需要或希望有生物降解性能场合应用的润滑剂。
在研制可生物降解的润滑剂当中，人们关心为使用这种润滑剂于实际应用中并将其分散排入例如江河，海洋和湖泊的水域中所产生的后果已引起与环境相关机构和润滑剂制造商的密切关注。人们热切期望合成润滑剂既保持它的冷流性能和添加剂的溶解性能又不会丧失它的生物降解作用和润滑作用。
可生物降解的润滑剂应用(例如双冲程发动机油，弹射器油，液压流体，钻孔流体，水轮机油，齿轮油，润滑脂和压缩机油)的基料一般应满足五个准则：(1)所用的分散剂和其它添加剂例如聚酰胺的可溶性；(2)良好的冷流性能(例如，倾点低于-40℃，在-25℃黏度小于7500厘泊)；(3)充分的生物降解性能以弥补加入到制成的润滑剂中的任何分散剂和其它添加剂的低生物降解性能；(4)不用加入抗磨耗添加剂就具有良好的润滑性能；(5)高闪点(高于175℃，由COC(克利弗兰得开杯)通过ASTM试验编号D-92测定的闪点和着火点)。
1979年12月，经济合作和发展组织(OECD)公开了用于降解和堆积试验的试验指南草案。专家组推荐使用下列试验确定有机化合物的“易生物降解性能”：改进的OECD筛选试验，改进的MITI试验(I)，闭瓶试验(Closed Bottle Test)，改进的Sturm试验和改进的AFNOR试验。专家组还推荐以下为具有“易生物降解性能”的证据：上述试验的结果分别为(溶解有机碳(DOC))70％；(生物需氧量(BOD))60％；(总有机碳(TOD))60％；(CO2)60％；以及(DOC)70％。用改进的Sturm试验，在28天获得生物降解的合格水平为至少(CO2)60％。
用于在改进的Sturm试验下，试验化学物的“易生物降解性能”的OECD指南(1981年5月12日正式批准，在此并入本文作为参考)包括测量试验化合物产生的CO2总量，并且以基于从试验化合物的碳含量计算得到的理论上的C2O(TCO)的百分数表示。因此，生物降解性能以TCO2的％表示。通过将试验物质加到化学上确定的液体介质(基本没有其它有机碳源)中，并用污物微生物培养，来进行改进的Sturm试验。以BaCO3形式捕集释放的CO2，在参照了适宜的空白对比后，在试验期内测定试验化合物产生的CO2总量，并计算基于由试验物质的碳组成理论计算应释放的CO2总量的百分数。参见G.van der Waal和D.Kenbeek的“对环境无害的酯类流体的试验，应用和前瞻(Test，Application and FutureDevelopment of Environmentally Friendly Ester Based Fluid”合成润滑剂杂志卷10，1993年4月出版第1期67-83页，结合入本文作为参考。
目前，一种通用的基料是菜籽油(即脂肪酸的甘油三酯，例如7％的饱和C12-C18酸，50％油酸，36％亚油酸和7％亚麻酸)，具有下列性能：在40℃黏度47.8厘沲，倾点0℃，闪点162℃和用改进的Sturm测定生物降解性能85％。虽然它具有优良的生物降解性能，但是由于它的低温性能和稳定性都比较差，所以限制了它在可生物降解的润滑剂中的应用。
除非它们具有足够低的分子量，由直链酸和直链醇合成的酯都趋向于具有较差的低温性能。即使由直链酸和高支链醇合成的酯例如直链酸的多元醇酯，实现具有优良低温性能的高粘度酯也相当困难。另外，直链酸的季戊四醇酯表现出对分散剂例如聚酰胺较差的溶解性能，低分子量(即碳原子数少于14)的直链酸的三羟甲基丙烷酯不能提供充分的润滑。这种低质量的润滑性能也出现在支链醇的己二酸酯中。由于低分子量的直链酯具有低黏度，要求一些支链度以增加黏度、同时还要保持优良的冷流性能。传统理论认为，酯的醇部分和酸部分都是高支链的时，例如在高支链酸的多元醇酯的情况下，产生的分子通过改进的Sturm试验(OECD试验编号301B)测定表现出较差的生物降解性能。
在Randles和Wright的论文“用于汽车和工程工业的对环境无害的酯润滑剂”合成润滑剂杂志，卷9-2，145-166页中，他们认为，缓慢或减缓微生物破坏的主要原因是支化的程度(它减缓β氧化)和酯水解被抑制的程度。在R.D.Swisher的名称为“表面活性剂的生物降解(Surfactant Biodegradation)”(Marcel Dekker.Inc.，第2版，1987，415-417页)的书中，进一步讨论了由于碳链支化对生物降解性能的负面影响。在Swisher的书中，他叙述到“结果清楚表明，随着支链的增多，对生物降解的阻力也会增大…虽然在直链分子中单个甲基支链的影响是微乎其微的，但通常也观察到随着支链的增多对生物降解的阻力会增大，而当在分子的所有链端发生季碳原子支链时，其阻力会格外大”。在N.S.Battersby，S.E.Pack和R.J.Watkinson的论文“在CEC-L-33-T-82中的油产品的生物降解性能和改进的Sturm试验之间的相互关系”Chemosphere，24(12)，1989-2000页中也讨论了烷基支链对生物降解性能的负面影响。
起初，人们认为支链多元醇酯的生物降解性能差是由于支化的作用，以及影响较小的在水中酯分子的不溶解性的影响。然而，通过本发明者近期的工作(公开在1994年12月8日申请的共同申请未决的美国专利申请序列号08/351,990中，在此结合入本文作为参考)表明，这些支链酯的非生物降解性能，位阻现象的作用比微生物不能破坏三级和四级碳原子的作用要大。因此，通过消除在酯键(键组)周围的位阻现象，用支链酯可更容易产生生物降解性能。
合成的支链多元醇酯广泛使用于不能被生物降解的应用中，例如制冷润滑应用中，如果3，5，5-三甲基己酸以25摩尔％或以上被结合进该分子中时已证实是非常有效的。然而，用改进的Sturm试验(OECD 301B)测定三乙基己酸是不可生物降解的，即使结合以25摩尔％的3，5，5-三甲基己酸，由于在其中含有季碳原子，将会大大地降低生物降解性能。
同样，将三烷基乙酸(即新酸(neo acids))结合进多元醇酯中会产生非常有用的制冷润滑剂。然而，这些酸经改进的Sturm试验(OECD 301B)测定是不可生物降解的，并且不能被用来生成用于可生物降解应用的多元醇酯。此外，多元醇的全支链酸酯也被用作制冷油。然而，它们也被认为经改进的Sturm试验(OECD 301B)测定应当不能迅速的生物降解，因此不希望将它们用于可生物降解实际应用中。
虽然，为制冷应用从纯直链C5和C10酸制得的多元醇酯经改进的Sturm试验测定具有可生物降解性能，因为其黏度太低，所以它们不能在液压或双冲程发动机中用作润滑剂。研制润滑剂基料使其在可生物降解的润滑剂的实际应用中表现出要求的所有不同性能，即具有高黏度、低倾点、氧化稳定性和通过改进的Sturm试验测定的生物降解性能是非常困难的。
1989年5月2日授权的US-A-4826633(Carr等人)公开，通过三羟甲基丙烷和单季戊四醇中的至少一种与脂族单羧酸的混合物反应生成合成酯润滑剂基料。该酸混合物包括含有5-10碳原子的直链酸和6-10碳原子的异酸，优选异壬酸(即3，5，5-三甲基己酸)。这种基料和一般酯润滑剂添加剂组合混合，生成具有在99℃(210°F)至少5.0厘沲的黏度和倾点至少低至-54℃(-65°F)的润滑剂。这种润滑剂特别适用于气轮机中。Carr等人的专利与本发明不同有二个原因。第一，它优先使用3，5，5-三甲基己酸用作支链酸，其每个酸分子内含有季碳原子。3，5，5-三甲基己酸内的季碳原子抑制了多元醇酯产品的生物降解。其次，因为用高压示差扫描量热法(HPDC)测定，根据Carr等人的润滑剂表现非常稳定，即经约35-65分钟，微生物不能将它们分解。
因此，本发明公开了通过由多羟基化合物(例如TMP或NPG)和含有碳原子数在5-10、优选7-10的支链羰基合成酸形成的酯基料，可以得到具有良好的冷流性能、良好的分散剂溶解性能和良好的润滑性能的可生物降解的润滑剂，条件是上述羰基合成酸不包括2-乙基己酸。根据本发明使用的支链羰基合成酸可以增加黏度。并且这些酸中的多种异构体有助于实现低温性能。也就是说，支链羰基合成酸容许增加黏度而不用增加分子量。从而，与全直链可生物降解的润滑剂相比，支链的可生物降解的润滑剂提供了如下的多个优点：(1)降低了倾点，(2)提高了其它添加剂的溶解性，(3)提高了润滑油的去污性/分散性。
由本发明者编辑并在以下实施例中列举的数据表明，由全支链反应试剂例如TMP和异羰基合成辛酸(例如Cekanoic8)可形成可生物降解的合成酯。
相反，本发明者发现，如果酸主要在羰基的α-碳上具有支链，如2-乙基己酸(2EH)，则对于酶催化的化学侵蚀的位阻太大。因此，不是所有的支链酸都能很好的生产具有满意的可生物降解性能的多元醇酯。
因此，本发明涉及，通过由羰基合成法生成的支链酸酯化多羟基化合物合成可生物降解的合成酯基料。羰基合成法促使以下支链酸的形成，该支链酸在羰基的α-碳上具有很少的支链。由于羰基合成酸的支链远离酯键，即在羰基的β碳或更远的碳上，该键的酶催化裂解可以发生。
可生物降解的合成基料优选包括支链或直链醇和支链羰基合成酸的反应产品，所述的支链和直链醇具有通式R(OH)n，其中R是含有约2-20个碳原子的脂族或环脂族基(优选烷基)，n为至少2、多达约10，支链羰基合成酸含有碳原子数(即碳原子数指根据情况而定的或是在酸中或是在醇中的碳原子总数)在C5-C10、较优选C7-C10的范围内，条件是这种羰基合成酸不包含任意显著量的在羰基的α-碳上的具有支链(例如2-乙基己酸)的羰基合成酸异构体，并且用于形成可生物降解的合成酯基料的支链酸中不超过10％的支链酸含有季碳原子，其中该酯呈现出下列性能：用改进的Sturm试验测定在28天内至少60％的生物降解性，倾点低于-40℃，在-25℃黏度低于7500厘泊，此外，优选酯基料呈现出至少175℃的高闪点。
在最优选的实施方案中，希望支链酸具有多种异构体，优选多于3种异构体，更优选多于5种异构体。
支链或直链醇选自新戊二醇，三羟甲基丙烷，乙二醇或丙二醇，丁二醇，山梨醇和2-甲基丙二醇。
支链羰基合成酸每分子平均具有支链在约0.3-1.9的范围内，带有的支链优选在羰基的β碳上或更远的碳上。优选支链羰基合成酸是选自异戊酸、异己酸、异庚酸、异辛酸、异壬酸和异癸酸的至少一种酸，条件是异-壬酸不是3，5，5-三甲基己酸，因为后者具有季碳原子。
该可生物降解的润滑剂也可以是上述公开的支链合成酯和至少一种酯的掺合物，后者选自天然油(例如菜籽油)和其它可生物降解的合成酯。
这些可生物降解的合成基料特别适用于形成可生物降解的润滑剂，例如二冲程发动机油、可生物降解的弹射器油、可生物降解的液压流体、可生物降解的钻孔流体、可生物降解的水轮机油、可生物降解的润滑脂、可生物降解的压缩机油、可生物降解的齿轮油、功能流体和工业和发动机应用中需要和希望可生物降解场合的润滑剂。
根据本发明制备的可生物降解的润滑剂优选含有约50-99wt％至少一种上述的可生物降解的润滑剂合成基料、约1-20wt％的润滑剂添加剂组分和约0-20％的溶剂。
图1是新戊二醇和三羟甲基丙烷的生物降解(改进的Sturm试验)百分率的图；
图2是由Cekanoic8形成的合成多元醇酯的生物降解(改进的Sturm试验)百分率的图；
图3是支链羰基合成C8酸和2-乙基己酸形成的二种合成多元醇酯分别暴露在环境中时随时间变化的生物降解(改进的Sturm试验)百分率的图。
根据本发明的用于各种可生物降解的润滑剂和油形成的支链合成酯基料优选由多元醇酯和支链C5-C10的羰基合成酸、例如异-羰基合成辛酸(Cekanoic8)的反应产品形成。
在可与本发明的支链和直链酸反应的醇中，例如是通式如下的多元醇(即多羟基化合物)：
R(OH)n
其中R是脂族或环脂族烃基(优选烷基)和n是至少2。烃基可含有约2-20或以上的碳原子，烃基还可含有取代基例如氯、氮和/或氧原子。多羟基化合物一般含有约2-10个羟基，较优选约2-6个羟基。多羟基化合物可含有一或多个氧亚烷基，这样，多羟基化合物包括例如聚醚多元醇的化合物。在用于形成羧酸酯的多羟基化合物中含有的碳原子数(即C数量)和羟基基团数(即羟基数量)可在宽范围内变化。
下列醇特别可用作多元醇：新戊二醇，2，2-二羟甲基丁烷，三羟甲基乙烷，三羟甲基丙烷，三羟甲基丁烷，乙二醇，丙二醇，聚烷二醇(例如聚乙二醇，聚丙二醇，聚丁二醇等，和其共聚物例如乙二醇和丙二醇的共聚物)。
优选的支链或直链醇选自新戊二醇，三羟甲基丙烷，三羟甲基乙烷，丙二醇，1，4-丁二醇，山梨醇等和2-甲基丙二醇。最优选的醇是三羟甲基丙烷和新戊二醇。
支链羰基合成酸
优选支链羰基合成酸是羰基合成单-羧酸，所述的羰基合成单-羧酸含有碳原子数为C5-C10、优选C7-C10，其中优选甲基支化的。优选的支链羰基合成酸是其中少于或等于10％的支链酸含有季碳原子的支链酸。羰基合成单-羧酸是至少一种选自下列酸的酸：异戊酸，异己酸，异庚酸，异辛酸，异壬酸和异癸酸；条件是，主要在羰基的α碳上有支链的羰基合成酸例如2-乙基己酸(2EH)不包括在本发明的支链羰基合成酸中。最优选的支链酸是异-羰基合成辛酸，例如Cekanoic 8酸。虽然，2-乙基己酸是异-C8酸并有时也被称作羰基合成酸，该酸是经由包括羰基化反应以及随后的醇醛缩合反应的双步骤方法形成的，因此不是本发明定义的“羰基合成酸”。
优选在本文中的“∝-碳”指的是沿着碳链的最接近羰基碳的碳原子。因此，β-碳是紧跟在∝-碳的碳，而更远的碳是那些连接到β-碳上的和更远的碳。
术语“异”指的是该产品是通过羰基合成法制成的多种异构体产品。本领域的专业人员虽然一般认为异-壬酸是3，5，5-三甲基己酸，但在用于本发明中时，它应当指的是由异-辛烯的羰基合成形成的多种异构体产品，并且应特别排除3，5，5-三甲基己酸。
希望包含多种异构体的支链羰基合成酸，优选多于3种异构体，最优选多于5种异构体。
通过将工业上的支链C4-C9烯烃馏分羰基化成相应的含支链C5-C10醛的羰基化反应产物，可以在所谓“羰基合成法”中生产支链羰基合成酸。在形成羰基合成酸的方法中，希望由上述羰基化反应产物形成醛中间体，接着转化粗羰基合成醛产品到羰基合成酸。羰基合成酸是用于生产根据本发明的可生物降解的合成多元醇酯的关键反应剂。
为了工业上生产羰基合成酸，可调节羰基化方法以生成最多量的羰基合成醛。这可通过控制温度，压力，催化剂浓度和/或反应时间来实现。之后，蒸馏脱金属的粗醛产品以从羰基合成醛中除去羰基合成醇，然后，根据以下的反应氧化生成所希望的羰基合成酸：
式中R是支链烷基；
另外，羰基合成酸可通过在没有氢并在形成酸的催化剂存在下使脱金属的粗醛产品和水反应来制备，其反应条件为温度在约93-205℃，压力在约0.1-6.99MPa，从而转化浓缩的富醛产品成为粗酸产品，并分离粗酸产品成为富酸产品和贫酸产品。
从烯烃原料流钴催化羰基化生产支链羰基合成酸的方法优选包括下列步骤：
(a)在羰基化催化剂存在下和在促使粗富醛反应产品生成的反应条件下，通过与一氧化碳和氢(即合成气)反应羰基化烯烃原料流；
(b)脱金属粗富醛反应产品，以从中回收羰基化反应催化剂和基本上无催化剂的粗富醛反应产品；
(C)分离无催化剂的粗富醛反应产品成为浓缩的富醛产品和贫醛产品；
(d)使浓缩的富醛产品和(i)氧(非强制性的采用催化剂)或(ii)在生成酸催化剂存在下和没有氢的状态下与水反应，从而将浓缩的富醛产品转换成为粗酸产品；和
(E)将粗酸产品分离成为支链羰基合成酸和贫酸产品。
优选烯烃原料流是任意的C4-C9烯烃，较优选支链C7烯烃。因此，优选烯烃原料流是支链烯烃，但在本文中也包括了能够生产所有支链羰基合成酸的直链烯烃。羰基化和后续的将粗羰基化产品和(i)氧(例如空气)或(ii)在生成酸的催化剂存在下与水的反应能够生产支链C5-C10酸，较优选支链C8酸(即Cekanoic 8酸)。每个由支链羰基合成醛转化形成的支链羰基合成C5-C10酸一般含有支链羰基合成酸异构体的混合物，例如Cekanoic 8酸含有26wt％3，5-二甲基己酸，19wt％4，5-二甲基己酸，17wt％3，4-二甲基己酸，11wt％5-甲基庚酸，5wt％4-甲基庚酸和22wt％单甲基庚酸和二甲基己酸的混合物。
本领域的专业人员熟知的能够转化羰基合成醛成为羰基合成酸的任何类型的催化剂都可用于本发明。优选的产生酸的催化剂公开在共同申请未决的并共同转让的在1994年6月23申请的美国专利申请序列号为08/269,420(Vargas等人)中，结合入本文作为参考。形成酸的催化剂被载附的金属或双金属催化剂是优选的。一种这样的催化剂是载于氧化铝或硅石-氧化铝上的双金属镍-钼催化剂，该催化剂含磷量为基于催化剂总重量的0.1-1.0wt％。另一种催化剂可通过使用磷酸作为溶剂将钼盐浸渍到氧化铝载体上制备。还有另一种含双金属的无磷的Ni/Mo催化剂可用于转化羰基合成醛成为羰基合成酸。
支链的合成酯基料可用来和选择的润滑剂添加剂一起形成可生物降解的润滑剂。列于下面的添加剂一般使用量应能使它们具有正常的功能。每个成分的典型用量列于下面，优选可生物降解的润滑剂含有约80wt％或以上的基料和20wt％的下列添加剂的任意组合：
(一般的) (优选的)
Wt％ Wt％
黏度指数改进剂 1-12 1-4
腐蚀抑制剂 0.01-3 0.01-1.5
氧化抑制剂 0.01-5 0.01-1.5
分散剂 0.1-10 0.1-5
润滑油流动改进剂 0.01-2 0.01-1.5
去污剂和防锈剂 0.01-6 0.01-3
倾点下降剂 0.01-1.5 0.01-1.5
消泡剂 0.001-0.1 0.001-0.01
抗磨损剂 0.001-5 0.001-1.5
密封膨胀剂 0.1-8 0.1-4
摩擦改进剂 0.01-3 0.01-1.5
可生物降解的合成酯基料 ≥80％ ≥80％
当使用其它的添加剂时，希望但不是必须制备包括分散剂与一种或多种的其它添加剂(浓缩物，当为添加剂混合物时，在本文中称作添加剂组合)的浓缩溶液或分散体(浓缩量如上面所述)的添加剂浓缩物，从而使几种添加剂同时被加入到基料中以形成润滑油组合物。使用溶剂或进行混合时适度的加热可以促使添加剂浓缩物溶解到润滑油中，但这不是必需的。一般，形成的浓缩物或添加剂组合含有适量的分散剂添加剂和任选的辅助添加剂，以便当添加剂组合和主要量的基本润滑剂或基料结合时在最后的组合物中提供所需的浓度。这样，本发明的可生物降解的润滑剂一般可使用高达20wt％添加剂组合，剩余的是可生物降解酯基料和/或溶剂。
在本文中，所有的重量百分数(除非另外说明)均基于添加剂的活性成分(A.I)含量和/或所有添加剂组合的总重量或每个添加剂的A.I重量加上总油或稀释剂的重量的总和。
上述用于可生物降解的润滑剂的添加剂的实例记载在下列文献中，结合入本文作为参考：1994年4月26日授权的US-A-5306313(Emert等人)；1994年5月17日授权的US-A-5312554(Waddoups等人)；1994年7月12日授权的US-A-5328624(Chung)；Benfaremo和Liu的论文“曲柄发动机油添加剂”润滑Texaco Inc 1-7页；Liston的论文“发动机润滑剂添加剂的组成和功能(Engine Lubricant Additives What They areand How They Function”润滑工程1992年5月389-397页。
黏度改进剂赋予润滑油高温和低温操作性能，容许润滑油在升温下保持剪切稳定性，以及在低温时表现出可容许的黏性和流动性。这些黏度改进剂通常是高分子量的烃聚合物，包括聚酯。黏度改进剂还可衍生出包括其它的性能或功能，例如附加的分散性能。适宜的黏度改进剂的典型实例可以是本领域熟知的任意类型，包括聚异丁烯，乙烯和丙烯的共聚物，聚甲基丙烯酸酯，甲基丙烯酸酯共聚物，不饱和二羧酸和乙烯基化合物的共聚物，苯乙烯和丙烯酸酯的共聚物和苯乙烯/异戊二烯、苯乙烯/丁二烯、异戊二烯/丁二烯的部分加氢共聚物，以及丁二烯和异戊二烯部分加氢均聚物。
腐蚀抑制剂也被称作抗腐蚀剂，可以减缓与润滑油组合物接触的金属部件的降解。腐蚀抑制剂的实例是磷硫化烃以及磷硫化烃和碱土金属氧化物或氢氧化物并优选在烷基化酚或烷基化酚硫酯存在下，也优选在二氧化碳存在下反应获得的产品。通过适宜的烃例如萜烯，C2-C6烯烃聚合物例如聚异丁烯的重油馏分和5-30％的硫化磷反应制备磷硫化烃，其条件为用1/2-15小时，温度范围为约66-316℃。在US-A-1969324中公开了一种方法可使磷硫化烃中和。
氧化抑制剂或抗氧剂可减缓在运行中矿物油变质的趋势，这种变质可以通过在金属表面上沉积的诸如污物、类油漆等的氧化产品和通过黏度增长得到证明。这种氧化抑制剂包括优选具有C5-C12烷基侧链的烷基-酚硫酯的碱土金属盐，例如壬基酚硫化钙，辛基苯基硫化钡，二辛基苯基胺，苯基α萘基胺，磷硫化烃或硫化烃等。
摩擦改进剂赋予润滑油组合物例如自动输送流体适宜的摩擦特性。适宜的摩擦改进剂的典型实例是脂肪酸酯和酰胺，聚异丁烯基琥珀酐-氨基醇的钼配合物，二聚脂肪酸的甘油酯，烷膦酸盐，含油酰胺的膦酸酯，S-羧基亚烷基烃基琥珀酰亚胺，N(羟烷基)链烯基琥珀酰胺酸或琥珀酰亚胺，二-(低级烷基)亚磷酸盐，以及磷硫化的N(羟烷基)链烯基琥珀酰亚铵的环氧化物和烯化氧加合物。最优选的摩擦改进剂是烃基取代的琥珀酸或酐和硫连双-链烷醇的琥珀酸酯或其金属盐。
分散剂保持油中的不溶解物(在使用时由氧化作用引起的)在流体中呈悬浮状，防止污物的絮凝和沉淀或在金属部件上沉积。适宜的分散剂包括高分子量的烷基琥珀酰亚铵，油溶性的聚异丁烯琥珀酸酐和亚乙基胺例如四亚乙基五胺的反应产品和其硼酸盐。
倾点下降剂(也被称作润滑油流动改进剂)降低了流体可流动或倾泻的温度。这种添加剂是人们熟知的，一般，这种添加剂的典型实例(即优化流体的低温流动性的添加剂)是富马酸C8-C18二烷基酯乙酸乙酯共聚物，聚甲基丙烯酸酯，和蜡萘。通过聚硅氧烷型、例如硅油和聚二甲基硅氧烷的消泡剂可提供泡沫控制。
抗磨损剂如其名可减缓金属部件的磨损。一般，抗磨损剂的典型实例是二烷基二硫代磷酸锌和二芳基二硫代磷酸锌。
消泡剂在润滑剂中被用于控制泡沫。通过高分子量的二甲基硅氧烷和聚酯的消泡剂可提供泡沫控制。聚硅氧烷型消泡剂的实例是硅油和聚二甲基硅氧烷。
去污剂和金属防锈剂包括硫酸的、烷基酚的、硫化烷基酚的、水杨酸烷基酯的、环烷酸的和其它油溶性的单-和双-羧酸的金属盐。高碱(即高碱性的)金属盐，例如高碱性的碱土金属磺酸盐(特别是Ca和Mg盐)是经常使用的去污剂。
密封膨胀剂包括诱发发动机密封膨胀型的矿物油，包括8-13碳原子的脂族醇例如十三烷基醇，优选的密封膨胀剂是在US-A-3974081(结合入本文作为参考)中公开的其特征是油溶性饱和10-60碳原子和2-4键合的脂族酯或芳族烃基酯，例如邻苯二甲酸二己酯。
支链合成酯基料可用于和选择的润滑剂添加剂一起配制可生物降解的二冲程发动机油。优选的可生物降解的二冲程发动机油一般是使用本发明可生物降解的合成酯基料与任意的常规双冲程发动机油添加剂组合一起构成的。下面列出的添加剂的一般使用量应能使它们具有正常的功能。添加剂组合可包括(但不限于此)黏度指数改进剂，腐蚀抑制剂，氧化抑制剂，偶合剂，分散剂，耐特压剂，色质稳定剂，表面活性剂，稀释剂，去污剂和防锈剂，倾点下降剂，消泡剂和抗磨损剂。
根据本发明的可生物降解的双冲程发动机油一般可使用约75-85％基料、约1-5％溶剂和剩余量的包括添加剂组合的组分。
上述的用于可生物降解的润滑剂的添加剂的实例公开在下列文献中(在此结合入本文作为参考)：1987年5月5日授权的US-A-5663063(Davis)；1994年6月19日授权的US-A-5330667(Tiffany，III等)；1988年4月26日授权的US-A-4740321(Davis等人)；1994年6月14日授权的US-A-5321172(Alexander等人)；和1991年9月17日授权的US-A-5049291(Miyaji等人)。
弹射器是在航天飞行器运载工具上在水面弹射航天飞行器脱离运载工具时使用的设备，支链合成酯基料可用于和选择的润滑剂添加剂一起配制可生物降解的弹射器油。优选的可生物降解的弹射器油一般使用本发明可生物降解的合成酯基料与任意的常规弹射器油添加剂组合一起构成。下面列出的添加剂的用量应能使它们具有正常的功能。添加剂组合可包括(但不限于此)黏度指数改进剂，腐蚀抑制剂，氧化抑制剂，耐特压剂，色质稳定剂，去污剂和防锈剂，消泡剂，抗磨损剂和摩擦改进剂。
根据本发明的可生物降解的弹射器油一般可使用约90-99％的基料和剩余量的包括添加剂组合的组分。
可生物降解的弹射器油优选包括常规腐蚀抑制剂和防锈剂。如果需要，弹射器油可含有其它的常规添加剂，例如消泡剂，抗磨损剂，其它抗氧化剂，耐特压剂，摩擦改进剂和其它的水解稳定剂。这些添加剂公开在Klamannn，“润滑剂和相关产品”，Verlag Chemie，DeerfieldBeach，1984中，结合入本文作为参考。
支链合成酯基料可用于和选择的润滑剂添加剂一起配制可生物降解的液压流体。优选的可生物降解的液压流体一般使用本发明可生物降解的合成酯基料与任意的常规液压流体添加剂组合一起形成。下面列出的添加剂的使用量应能使它们具有正常的功能。添加剂组合可包括(但不限于此)黏度指数改进剂，腐蚀抑制剂，界面润滑剂，破乳剂，倾点下降剂和消泡剂。
根据本发明的可生物降解的液压流体，一般可使用90-99％基料和剩余量的包括添加剂组合的组分。
其它添加剂公开在1988年11月8目授权的US.A.4783274(Jokinen等人)，结合入本文作为参考。
支链合成酯基料可用于与选择的润滑剂添加剂一起配制可生物降解的钻孔流体，优选的可生物降解的钻孔流体使用本发明可生物降解的合成酯基料和任意的常规的钻孔流体添加剂组合一起构成。下面列出的添加剂的用量应能使它们具有正常的功能，添加剂组合可包括(但不限于此)黏度指数改进剂，腐蚀抑制剂，湿润剂，失水改进剂，杀菌剂和钻孔钻润滑剂。
根据本发明的可生物降解的钻孔流体，一般可使用约60-90％基料、约5-25％溶剂和剩余量的包括添加剂组合的组分。参见1983年5月3日授权的US-A-4382002(Walker等人)，结合入本文作为参考。
适宜的烃溶剂包括：矿物油，特别具有良好氧化稳定性和沸点在200-400℃的石蜡基油，例如由Exxon Chemical Americas，Houston，Texas出售的Mentor28；柴油和汽油；和重质芳族石脑油。
支链合成酯基料可用于与选择的润滑剂添加剂一起配制水轮机油，优选的可生物降解的水轮机油一般使用本发明可生物降解的合成酯基料和任意的常规的水轮机油添加剂少量组分一起构成。下面列出的添加剂一般使用量应能使它们具有正常的功能。添加剂组合可包括(但不限于此)黏度指数改进剂，腐蚀抑制剂，氧化抑制剂，增稠剂，分散剂，抗乳化剂，色质稳定剂，去污剂和防锈剂和倾点下降剂。
根据本发明的可生物降解的水轮机油，一般可使用约65-75％基料、约5-30％溶剂和剩余量的包括添加剂组合的组分，添加剂按组合物的总重量计一般在约0.01-5.0wt％的范围内。
支链合成酯基料可用于与选择的润滑剂添加剂一起配制可生物降解的润滑脂，在润滑脂中的主要成分是增稠剂或胶凝剂，润滑剂配方的不同常常是由于这种组分的不同造成的。除增稠剂或胶凝剂之外，可通过特殊的润滑基料和可使用的各种添加剂影响润滑脂的其它性能和特性。
优选的可生物降解的润滑脂一般由本发明可生物降解的合成酯基料和任意的常规润滑脂添加剂组合一起构成。一般，下面列出的添加剂的使用量应能使它们具有正常的功能。添加剂组合可包括(但不限于此)黏度指数改进剂，氧化抑制剂，耐特压剂，去污剂和防锈剂，以及增稠剂或胶凝剂。
根据本发明的可生物降解的润滑脂，一般可使用约80-95％基料、约5-20％增稠剂或胶凝剂和剩余量的包括添加剂组合的组分。
一般润滑脂组合物中使用的增稠剂包括碱金属皂，粘土，聚合物，石棉，碳黑，硅胶，聚脲和铝配合物。皂增稠的润滑脂是最流行的，其中最常用的是锂和钙的皂。从长链脂肪酸碱金属盐和1，2-羟基硬脂酸锂制备简单皂润滑脂，后者主要从1，2-羟基硬脂肪酸、氢氧化锂一水合物和矿物油制备。配合的皂式润滑脂也是普遍使用的，其包括有机酸的混合物的金属盐。目前常用的一种配合皂润滑脂是一种配合锂皂润滑脂，它是由1，2-羟基硬脂肪酸、氢氧化锂一水合物、壬二酸和矿物油制备的。对锂皂描述和举例的专利包括1973年9月11日授权的US-A-3758407(Harting)；1974年2月12日授权的US-A-3791973(Gilani)；1975年12月30日授权的US-A-3929651(Murray)和1983年7月12日授权的US-A-4392967(Alexander)(上述专利结合入本文作为参考)。
在Boner的“现代润滑用润滑脂”1976，第五章中描述了在润滑脂中可用的添加剂和在上述其它可生物降解的产品中可用的添加剂(结合入本文供作参考)。
支链合成酯基料可用于与选择的润滑剂添加剂一起组成可生物降解的压缩机油。优选的可生物降解的压缩机油一般是由本发明的可生物降解的合成酯基料与任意的常规压缩机油添加剂组合一起组成，下面列出的添加剂一般用量应能使它们具有正常的功能。添加剂组合可包括(但不限于此)氧化抑制剂，添加剂增溶剂，防锈剂/金属钝化剂，破乳剂和抗磨损剂。
根据本发明的可生物降解的压缩机油，一般可使用约80-99％基料、约1-15％溶剂和剩余量的包括添加剂组合的组分。
在1992年10月20日授权的US-A-5156759中描述了压缩机油的添加剂(结合入本文作为参考)。
实例1
下列是普通的酯基料，在使用中用作可生物降解的润滑剂不能表现满意的性能。在表1中列出的性能是用下列方法测定的，倾点是用ASTM#D-97测定。Brookfield黏度是在-25℃用ASTM#D2983测定。运动黏度(@40和100℃)是用ASTM#D-445测定。生物降解性是用改进的Sturm试验(OECD试验号.301B)测定。通过掺合所需的比例并观察光雾(haze)、浊度、分相等测定分散剂的溶解性。发动机磨损是用NMMAYamaha CE50S润滑试验测定。
表1基料 倾点 黏度 黏度 黏度 分散剂 发动机
℃ -25℃(厘泊) 40℃(厘沲) 100℃(厘沲) ％生物降解 溶解性* 磨损天然油菜籽油 0 固体 47.80 10.19 86.7 n/a n/a全直链酯己二酸二-十一烷基酯 +21 固体 13.92 2.8 n/a n/a n/a多羟基化合物w/直链&半直链酸TPE/C810/C7酸 n/a 固体 29.98 5.90 n/a n/a n/aTPE/DiPE/n-C7 -45 1380 24.70 5.12 82.31 H 失败TPE/C7酸 -62 915 24.0 4.9 83.7 H 失败TMP/n-C7，8，10 -85 350 17.27 4.05 61.7** C 失败TMP/C7酸 -71 378 14.1 3.4 76.5 C 失败支链己二酸酯己二酸二-十三烷基酯 -62 n/a 26.93 5.33 65.99 C 失败
*表示分散剂的溶解性：H＝光雾；C＝透明。
**表示包括15.5wt％分散剂的这种材料的生物降解。
n/a表示没有获得数据。
TPE表示工业级季戊四醇。
TMP表示三羟甲基丙烷。
C810表示主要成分为正辛酸和正癸酸的混合物，可含有少量的n-C6和n-C12酸。C810的典型样品例如可含有：3-5％n-C6，48-58％n-C8，36-42％n-C10，和0.5-1％n-C12。
n-C7，8，10表示带有7，8和10个碳原子的直链酸的混合物，例如37摩尔％n-C7酸、39摩尔％n-C8酸、21摩尔％n-C10酸和3摩尔％n-C6酸。
C7表示通过己烯-1的钴催化羰基合成反应生产的C7酸，含有70％的直链的和30％的α-支链的。该组合物包括约70％正庚酸，22％2-甲基己酸，6.5％2-乙基戊酸，1％4-甲基己酸和0.5％3.3-二甲基戊酸。
菜籽油是一种天然油，很容易生物降解，但是它的低温性能非常差，由于它不稳定因此它的润滑性能也不好。菜籽油在发动机内很不稳定并且容易分解常常引起沉淀形成，污垢和腐蚀问题。己二酸二-十一烷基酯或许可生物降解，但是它的低温性能很差。低分子量的直链酸的多元醇酯不能提供润滑作用，而高分子量的直链或半直链酸的多元醇酯低温性能较差。此外，直链酸的季戊四醇酯不溶解聚酰胺分散剂。己二酸二-十三烷基酯仅勉强可生物降解，当与也只有低度的生物降解性的分散剂掺合时，所生成的油仅有约45％的生物降解性。此外，己二酸二-十三烷基酯不能提供润滑作用。低分子量的支链己二酸酯例如己二酸二异癸基酯较易生物降解，但不能提供润滑作用并可引起密封膨胀问题。
实例2
本发明者用新戊二醇和三羟甲基丙烷在改进的Sturm试验下进行对比试验以测定可生物降解的性能，结果示于图1，从中可以看出，新戊二醇和三羟甲基丙烷没有显著的可生物降解性。
实例3
本发明者对二个支链的合成多元醇酯，即新戊二醇和支链羰基合成C8酸(NPG/i-C8)的酯和三羟甲基丙烷和支链羰基合成C8酸的酯使用改进的Sturm试验测定％生物降解性能。在改进的Sturm试验中，通过用支链羰基合成C8酸酯化NPG和TMP生成的酯呈现出生物降解性能(即在28天内60％以上的生物降解性)。
出人意料的是，当用支链羰基合成C8酸酯化NPG和TMP时，得到的酯在改进的Strum试验中证明是可生物降解的，即使NPG和TMP它们自身表现出几乎没有可生物降解性能。
实例4
本发明者进行试验，数据列于图3，其中，由改进的Mturm试验测定，2-乙基己酸(即异-C8酸)与三羟甲基丙烷的酯的最大可生物降解性能是5％；支链羰基合成C8酸(即Cekanoic8)与三羟甲基丙烷的酯的最大可生物降解性能是67％。本发明者认为，这种意外的结果是由于支链羰基合成C8酸的独特的结构性能引起的。也就是说，TMP/支链羰基合成C8酸的酯呈现出较大的可生物降解性能主要是由于采用羰基合成法制备这种羰基合成异辛酸。在混合的支链庚烯的原料流上采用羰基合成法或羰基化方法生产的支链C8羰基合成酸，该酸沿链在∝碳上几乎没有支链。因为支链远离酯键(即在β碳和更远碳上)，酯键的酶催化的裂解可以发生。
Claims (27)
1.一种可生物降解的合成酯基料，它包括下列物质的反应产物：
选自新戊二醇、三羟甲基丙烷、乙二醇或丙二醇、丁二醇、山梨醇和2-甲基丙二醇的支链或直链醇；和
至少一种含有碳数在约C5-C10之间的支链羰基合成酸，其中，支化是在β-碳或更远的碳上，条件是所述支链羰基合成酸不包括2-乙基己酸；其中所述的酯基料呈现下列性能：用改进的Sturm试验测定在28天内至少60％的生物降解性；倾点低于-25℃；和在-25℃粘度低于7500cps。
2.根据权利要求1的可生物降解的合成酯基料，其中通过下列步骤制备所述的多种支链酸异构体：
(a)在羰基化催化剂存在下和在促使粗富醛反应产品生成的反应条件下，通过与一氧化碳和氢反应羰基化C4-C9烯烃原料流；
(b)将粗富醛反应产品脱金属，以从中回收羰基化催化剂和基本上无催化剂的粗富醛反应产品；
(C)分离无催化剂的粗富醛反应产品成为浓缩的富醛产品和贫醛产品；
(d)使浓缩的富醛产品和(i)氧或(ii)在生成酸催化剂存在下和没有氢的状态下与水反应，从而将浓缩的富醛产品转换成为粗酸产品；和
(E)将粗酸产品分离成为所述多种支链酸异构体和贫酸产品。
3.根据权利要求2的可生物降解的合成酯基料，其中所述的多种支链酸异构体是多种异辛酸并包括3，5-二甲基己酸、4，5-二甲基己酸、3，4-二甲基己酸、5-甲基庚酸、4-甲基庚酸以及混合的甲基庚酸和二甲基己酸的混合物。
4.根据权利要求1的可生物降解的合成酯基料，其中所述的多种支链酸异构体是约C7-C10酸。
5.根据权利要求1的可生物降解的合成酯基料，其中所述的多种支链酸异构体含有至少3种异构体。
6.根据权利要求1的可生物降解的合成酯基料，其中所述的酯还呈现高闪点COC为至少175℃。
7.根据权利要求1的可生物降解的合成酯基料，其中所述的多种支链酸异构体包括选自异戊酸、异己酸、异庚酸、异辛酸、异壬酸和异癸酸的至少一种酸，条件是所述的异壬酸不是3，5，5-三甲基己酸。
8.一种可生物降解的润滑剂，它由至少一种可生物降解的合成酯基料和润滑剂添加剂组合制备，所述的可生物降解的合成酯基料包括支链醇或直链醇和至少一种支链羰基合成酸的反应产物，所述的支链醇或直链醇选自新戊二醇、三羟甲基丙烷、乙二醇或丙二醇、丁二醇、山梨醇和2-甲基丙二醇，所述的支链羰基合成酸的碳数在约C5-C10之间，其中，支化是在β-碳或更远的碳上，条件是所述支链羰基合成酸不包括2-乙基己酸；其中所述的酯基料呈现下列性能：用改进的Sturm试验测定在28天内至少60％的生物降解性；倾点低于-25℃；和在-25℃的粘度低于7500cps。
9.根据权利要求8的可生物降解的润滑剂，其中所述的可生物降解的润滑剂是所述的支链合成酯和至少一种选自菜籽油和其它合成酯的酯的掺合物。
10.根据权利要求8的可生物降解的润滑剂，其中所述的添加剂组合包括选自粘度指数改进剂、腐蚀抑制剂、氧化抑制剂、分散剂、润滑油流动改进剂、去污剂和防锈剂、倾点下降剂、消泡剂、抗磨损剂、密封膨胀剂和摩擦改进剂的添加剂。
11.根据权利要求8的可生物降解的润滑剂，其中所述的可生物降解的润滑剂是齿轮油。
12.根据权利要求8的可生物降解的润滑剂，其中所述的可生物降解的润滑剂是弹射器油。
13.根据权利要求12的可生物降解的润滑剂，其中所述的添加剂组合包括至少一种选自粘度指数改进剂、腐蚀抑制剂、氧化抑制剂、偶合剂、分散剂、耐特压剂、色质稳定剂、去污剂和防锈剂、消泡剂、抗磨损剂和摩擦改进剂的添加剂。
14.根据权利要求8的可生物降解的润滑剂，其中所述的可生物降解的润滑剂是液压流体。
15.根据权利要求14的可生物降解的润滑剂，其中所述的添加剂组合包括至少一种选自粘度指数改进剂、腐蚀抑制剂、界面润滑剂、破乳剂、倾点下降剂和消泡剂的添加剂。
16.根据权利要求8的可生物降解的润滑剂，其中所述的可生物降解的润滑剂是钻孔流体。
17.根据权利要求16的可生物降解的润滑剂，其中所述的添加剂组合包括至少一种选自粘度指数改进剂、腐蚀抑制剂、增重剂、失水改进剂、杀菌剂和钻孔钻润滑剂的添加剂。
18.根据权利要求8的可生物降解的润滑剂，其中所述的可生物降解的润滑剂是水轮机油。
19.根据权利要求18的可生物降解的润滑剂，其中所述的添加剂组合包括至少一种选自粘度指数改进剂、腐蚀抑制剂、氧化抑制剂、增稠剂、分散剂、抗乳化剂、色质稳定剂、去污剂和防锈剂以及倾点下降剂的添加剂。
20.根据权利要求8的可生物降解的润滑剂，其中所述的可生物降解的润滑剂是润滑脂。
21.根据权利要求20的可生物降解的润滑剂，其中所述的添加剂组合包括至少一种选自增稠剂、粘度指数改进剂、氧化抑制剂、耐特压剂、去污剂和防锈剂、倾点下降剂、金属减活化剂和抗磨损剂的添加剂。
22.根据权利要求8的可生物降解的润滑剂，其中所述的可生物降解的润滑剂是压缩机油。
23.根据权利要求22的可生物降解的润滑剂，其中所述的添加剂组合包括至少一种选自氧化抑制剂、去污剂和防锈剂、金属减活化剂、添加剂增溶剂、破乳剂和抗磨损剂的添加剂。
24.根据权利要求8的可生物降解的润滑剂，它还包括溶剂。
25.根据权利要求24的可生物降解的润滑剂，其中所述的可生物降解的合成酯基料存在量为约50-99wt％，所述的润滑剂添加剂组合存在量为约1-20wt％，和所述溶剂存在量为约0-30％。
26.根据权利要求8的可生物降解的润滑剂，其中所述的可生物降解的润滑剂是二冲程发动机油。
27.根据权利要求26的可生物降解的润滑剂，其中所述的添加剂组合包括至少一种选自粘度指数改进剂、腐蚀抑制剂、氧化抑制剂、偶合剂、分散剂、耐特压剂、色质稳定剂、表面活性剂、稀释剂、去污剂和防锈剂、倾点下降剂、消泡剂和抗磨损剂的添加剂。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/652,012 US5728658A (en) | 1996-05-21 | 1996-05-21 | Biodegradable synthetic ester base stocks formed from branched oxo acids |
| US08/652,012 | 1996-05-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1219193A CN1219193A (zh) | 1999-06-09 |
| CN1094507C true CN1094507C (zh) | 2002-11-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97194836A Expired - Fee Related CN1094507C (zh) | 1996-05-21 | 1997-05-21 | 由支链羰基合成酸制备的可生物降解的合成酯基料 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5728658A (zh) |
| EP (1) | EP0904338B1 (zh) |
| JP (1) | JP2000514470A (zh) |
| CN (1) | CN1094507C (zh) |
| AR (1) | AR007237A1 (zh) |
| AU (1) | AU724777B2 (zh) |
| BR (1) | BR9709330A (zh) |
| CA (1) | CA2253812C (zh) |
| DE (1) | DE69714732T2 (zh) |
| NO (1) | NO319757B1 (zh) |
| WO (1) | WO1997044416A1 (zh) |
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| US6656888B1 (en) * | 1992-08-28 | 2003-12-02 | Cognis Corporation | Biodegradable two-cycle engine oil compositions, grease compositions, and ester base stocks use therein |
| GB9523916D0 (en) * | 1995-11-22 | 1996-01-24 | Exxon Chemical Patents Inc | Two-cycle ester based synthetic lubricating oil (pt-1041) |
| FR2814087B1 (fr) * | 2000-09-15 | 2003-07-04 | Inst Francais Du Petrole | Formulation desemulsionnante en base huile et son utilisation dans les traitements des drains fores en boue a l'huile |
| DE10138686A1 (de) | 2001-08-07 | 2003-02-27 | Suedzucker Ag | Verwendung einer Polyester-Zusammensetzung als Hydraulikfluid |
| MY128504A (en) * | 2001-09-25 | 2007-02-28 | Pennzoil Quaker State Co | Environmentally friendly lubricants |
| AU2002367745B2 (en) | 2001-10-10 | 2007-05-10 | Exxonmobil Research And Engineering Company | Biodegradable non-toxic gear oil |
| WO2005077876A1 (ja) | 2004-01-28 | 2005-08-25 | Idemitsu Kosan Co., Ltd. | 長鎖分岐アルキル基含有カルボニル化合物 |
| JP4827381B2 (ja) * | 2004-01-30 | 2011-11-30 | 出光興産株式会社 | 生分解性潤滑油組成物 |
| US20070287636A1 (en) * | 2006-06-09 | 2007-12-13 | Sun Drilling Products Corporation | Drilling fluid additive and base fluid compositions of matter containing B100 biodiesels; and applications of such compositions of matter in well drilling, completion, and workover operations |
| CN201972923U (zh) | 2007-10-24 | 2011-09-14 | 艾默生环境优化技术有限公司 | 涡旋机 |
| JP5480079B2 (ja) * | 2010-09-14 | 2014-04-23 | 花王株式会社 | 潤滑油基油 |
| US8741822B2 (en) * | 2011-02-13 | 2014-06-03 | Trent University | Esters for use as a base stock and in lubricant applications |
| US8980808B2 (en) | 2011-08-03 | 2015-03-17 | Cognis Ip Management Gmbh | Lubricant compositions with improved oxidation stability and service life |
| WO2018118610A1 (en) * | 2016-12-22 | 2018-06-28 | Exxonmobil Research And Engineering Company | Aircraft turbine oil base stock and method of making |
| WO2019147515A1 (en) * | 2018-01-29 | 2019-08-01 | Exxonmobil Chemical Patents Inc. | Anaerobically biodegradable fluids for drilling applications |
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- 1997-05-21 AU AU30748/97A patent/AU724777B2/en not_active Ceased
- 1997-05-21 DE DE69714732T patent/DE69714732T2/de not_active Expired - Fee Related
- 1997-05-21 EP EP97925678A patent/EP0904338B1/en not_active Expired - Lifetime
- 1997-05-21 CN CN97194836A patent/CN1094507C/zh not_active Expired - Fee Related
- 1997-05-21 CA CA002253812A patent/CA2253812C/en not_active Expired - Fee Related
- 1997-05-21 BR BR9709330A patent/BR9709330A/pt not_active IP Right Cessation
- 1997-05-21 AR ARP970102152A patent/AR007237A1/es active IP Right Grant
- 1997-05-21 JP JP09542690A patent/JP2000514470A/ja active Pending
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Also Published As
| Publication number | Publication date |
|---|---|
| AU724777B2 (en) | 2000-09-28 |
| DE69714732T2 (de) | 2003-04-24 |
| DE69714732D1 (de) | 2002-09-19 |
| CA2253812C (en) | 2005-07-26 |
| AR007237A1 (es) | 1999-10-27 |
| JP2000514470A (ja) | 2000-10-31 |
| AU3074897A (en) | 1997-12-09 |
| WO1997044416A1 (en) | 1997-11-27 |
| BR9709330A (pt) | 1999-08-10 |
| CA2253812A1 (en) | 1997-11-27 |
| CN1219193A (zh) | 1999-06-09 |
| NO985415D0 (no) | 1998-11-20 |
| NO319757B1 (no) | 2005-09-12 |
| US5728658A (en) | 1998-03-17 |
| EP0904338B1 (en) | 2002-08-14 |
| EP0904338A1 (en) | 1999-03-31 |
| NO985415L (no) | 1999-01-19 |
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