CN1064703C - 可生物降解合成酯基本原料 - Google Patents
可生物降解合成酯基本原料 Download PDFInfo
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- CN1064703C CN1064703C CN95197393A CN95197393A CN1064703C CN 1064703 C CN1064703 C CN 1064703C CN 95197393 A CN95197393 A CN 95197393A CN 95197393 A CN95197393 A CN 95197393A CN 1064703 C CN1064703 C CN 1064703C
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Abstract
本发明公开了一种可生物降解的合成酯基本原料,它包括如下组分的反应产物:通式R(OH)n的支化或线型醇,其中R为具有约2至20个碳原子的脂族或环脂族基团,n至少为2;包括约30至80mol%的具有的碳原子数在约C5至C12之间的线型酸和约20至70mol%的至少一种具有的碳原子数在约C5至C13之间的支化酸的混合酸;其中所述酯基本原料显示如下性能:由改进Sturm试验测量在28天内至少60%生物降解;倾点低于-25℃;在-25℃时的粘度低于7500cps。
Description
本发明涉及支化合成酯用于改进可生物降解润滑剂基本原料的冷流性能和分散剂溶解性而不丧失可生物降解性或润滑性的用途。通过沿酯的酰基和/或的醇部分支化可达到至少60%的生物降解(由Modified Sturm试验测量)。这些支化合成酯特别适用于形成需要或希望生物降解的双循环发动机油、弹射器油、液压油、钻孔液体、水轮机油、润滑脂、压缩机油和其它工业或发动机应用中的可生物降解润滑剂。
本发明背景
对于开发最后将分散于水路如江河、海洋和湖泊的可生物降解润滑剂,在环境界和润滑剂制造业都已产生了很大兴趣。因此特别希望合成既保持其冷流性能又不丧失可生物降解性或润滑性能的润滑剂。
用于可生物降解润滑剂中(如双循环发动机油、弹射器油、液压油、钻孔液体、水轮机油、润滑脂和压缩机油)的基本原料通常应满足五个标准:(1)与分散剂和其它添加剂如聚酰胺的溶解性;(2)良好的冷流性能(如倾点低于-40℃;在-25℃时低于7500cp);(3)足够的可生物降解性能以弥补用于配制润滑剂的各种分散剂和/或其它添加剂的低生物降解性;(4)在不借助抗磨损剂下的良好润滑性;和(5)高闪点(高于260℃,闪点和着火点按照ASTM试验编号D-92通过COC(Cleveland Open Cup)测量)。
经济合作与发展组织(The Organization for Economic Cooperationand Development,OECD)在1979年12月颁布了降解和堆积试验标准草案。专家组推荐应将下列试验用于测定有机化学药品的“容易生物降解性”:改进OECD遮掩试验(Modified OECD Screening Test),改进MITI试验(Modified MITI Test)(I),闭瓶试验(Closed Bottle Test),改进Sturm试验(Modified Sturm Test)和改进AFNOR试验(ModifiedAFNOR Test)。专家组还推荐下列在28天内获得的可生物降解“通过水平”可被作为“容易生物降解”的良好依据:对于上述试验的试验值分别为(溶解有机碳(DOC))70%;(生物需氧量(BOD))60%;(总有机碳(TOD))60%;(CO2)60%;和(DOC)70%。因此,用改进Sturm实验测定在28天内获得的可生物降解“通过水平”为至少(CO2)60%。
由于设定28天试验期的主要目的是使微生物有足够的时间适应化学药品(迟延期),这样经相当短的适应期后应使降解慢的化合物不能通过试验。因此应检验生物降解速率。必须在生物降解开始后10天内达到生物降解通过水平(60%)。当排出占理论CO2量的10%的CO2时认为生物降解已经开始。换言之,容易生物降解的流体在28天内应具有至少60%的CO2收率,并且该水平必须在生物降解超过10%后10天内达到,这被称为“10天时限(10-Day window)”。
在改进Sturm试验(OECD 301B,1981年5月12日通过,这里作为参考引入)中测定化学药品的“容易生物降解”的OECD标准涉及由试验化合物产生的CO2的测量值,该测量值以由试验化合物的含碳量计算应产生的理论CO2(TCO2)的百分比表示。因此生物降解性表示为TCO2的百分比。改进Sturm试验通过将试验物质掺入基本无其它有机碳源的液体介质中并用污水微生物接种进行。释放出的CO2以BaCO3形式捕集。参考合适的空白对比物后,测定试验化合物在试验期间产生的CO2总量并按试验物质理论上基于碳的组成能够产生的总CO2的百分数计算。参见G.van der Waal和D.kenbeek,“环境有益酯基流体的试验、应用和未来发展”,合成润滑剂期刊,Vol.10,第1期,1993年4月,pp.67-83,这里作为参考引入。
目前普遍使用的一种基本原料是菜籽油(即脂肪酸的甘油三酯,例如7%饱和C12至C18酸,50%油酸、36%亚油酸和7%亚麻酸),它具有如下性能:在40℃时的粘度为47.8cSt,倾点0℃,闪点162℃,生物降解性能85%(通过改进Sturm试验)。尽管菜籽油具有非常好的生物降解性能,但因其低温性能和稳定性差因此用于可生物降解润滑剂受到限制。
除非它们的分子量足够低,否则由线型酸和线型醇合成的酯趋于具有不良低温性能。甚至当由线型酸和高度支化的醇合成诸如线型酸的多醇酯时,也难以获得具有良好低温性能的高粘度酯。此外,线型酸的季戊四醇酯呈现与分散剂如聚酰胺的不良溶解性,而低分子量(即碳原子数小于14)线型酸的三羟甲基丙烷酯不能提供足够的润滑性。这种质量较差的润滑性能在支化醇的己二酸酯中也能看到。由于低分子量线型酯同样具有低粘度,因此需要一定程度的支化以提高粘度,同时保持良好的冷流性能。然而,当酯的醇和酸部分被高度支化时(例如对于高度支化的含氧酸的多醇酯的情况),所得分子用改进Sturm试验(OECD 301B)测定显示不良生物降解性能。
Randels和Wright发表在合成润滑剂期刊,Vol.9-2,pp.145-161中的论文“用于汽车和发动机工业中的无污染酯润滑剂”中指出,减慢或降低微生物降解的主要因素是支化程度,它降低β-氧化,并抑制酯水解的程度。因沿碳链支化对生物降解性能的消极影响在R.D.Swisher编著的书“表面活性剂的生物降解”(Marcel Dekker,Inc.,第二版,1987),pp.415-417中进一步进行了讨论。Swisher在他的书中指出,“结果清楚地表明耐生物降解性随支化而增加…尽管仅在另外的线型分子中注意到单甲基支化的影响,但通常也观察到耐(生物降解性)随支化增加而提高,并且当四价支化出现在分子中的所有链末端时耐生物降解性变得特别大”。烷基支化对生物降解性能的消极影响还在N.S.Battersby,S.E.Pack和R.J.Watkinson发表的论文“油产品在CEC-L-33-T-82中的生物降解性能与改进Sturm试验之间的相关性”(臭氧层,24(12),pp.1989-2000(1992))中进行了讨论。
最初,人们认为支化多醇酯的不良生物降解性是由于支化的结果,且在较低程度上是由于支化分子在水中不溶解的结果。然而,本发明人最近的研究证明这些支化酯的非生物降解性在于空间位阻的作用比微生物不能断裂叔和季碳原子的作用更大。因此通过除去酯键周围的空间位阻,支化酯可更容易地生物降解。
支化的合成多醇酯已广泛用于非生物降解领域,如用作致冷润滑剂,并已证明若将25mol%或更多的3,5,5-三甲基己酸加入分子中更有效。然而,通过改进Sturm试验(OECD 301B)测定三甲基己酸是非生物降解的,即使加入25mol%的3,5,5-三甲基己酸,因含于其中的季碳原子也会显著降低多醇酯的可生物降解性能。
同样,将三烷基乙酸(即新酸)加入多醇酯可生产非常有用的致冷润滑剂。然而,通过改进Sturm试验(OECD 301B)测定这些酸不能生物降解,因此不能用于生产可生物降解应用的多醇酯。全支化酸的多醇酯都可用作致冷油。然而通过改进Sturm试验(OECD 301B)测定它们不能很快生物降解,因此不适于在生物降解应用中使用。
尽管由纯线型C5至C10酸制备的在致冷中应用的多醇酯经改进Sturm试验是生物降解的,但是它们不能在液压或双循环发动机中用作润滑剂,因为粘度太低需要加入抗磨损添加剂。要开发能够在可生物降解应用中显示所需的所有各种性能即高粘度、低倾点、氧化稳定性和可生物降解性(由改进Sturm试验测量)特别困难。
1989年5月2日授权的US 4,826,633(Carr等人)公开了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形成的合成酯润滑剂基本原料。酸混合物包括具有5至10个碳原子的直链酸和具有6至10个碳原子的异-酸,优选异-壬酸(即3,5,5-三甲基己酸)。将这种基本原料与常规酯润滑剂添加剂体系混合,形成在99℃(210°F)粘度至少为5.0厘沲和倾点至少低至-54℃(-65°F)的润滑剂。这种润滑剂特别适用于燃气涡轮发动机中。Carr等人的专利因两个原因与本发明不同。第一,优选使用在每个酸分子中含有一个季碳原子的3,5,5-三甲基己酸作为支化酸。包括于3,5,5-三甲基己酸中的季碳原子阻止了多醇酯产品的可生物降解性。此外,由于Carr等人的润滑剂显示高稳定性(通过高压差示扫描量热计(HPDSC)测量),即约35至65分钟,因此微生物不能使其分开。相反,本发明的润滑剂稳定性低,即它具有的HPDSC读数为约12至17分钟。较低的稳定性可使微生物进攻多醇结构的C-C键并使酯有效地进行生物降解。本发明润滑剂稳定性较低的一个原因是用于形成润滑剂酯基本原料的不多于10%的支化酸含有季碳原子。
因此,本发明人已发现,通过将支化酸加入酯分子中,可得到具有良好冷流性能、与分散剂的良好溶解性和良好润滑性能的用于高度可生物降解的润滑剂中的可生物降解基本原料。根据本发明需要使用支化酸以升高粘度,并且这些酸中的多种异构体有助于达到低温性能。换言之,支化酸可提高粘度而不升高分子量。同时,支化的可生物降解润滑剂与全线型可生物降解润滑剂相比具有下列附加优点:(1)倾点降低;(2)其它添加剂的溶解性增加;(3)润滑油的去垢/分散性增加;(4)在液压油和弹射器油应用中氧化稳定性增加。
由本发明人收集的并在下列实施例中提供的数据证明,所有上述性能完全可用加入高度支化酸和线型酸的可生物降解合成酯基本原料配制的可生物降解润滑剂达到。
本发明概述
可生物降解合成基本原料优选包括如下组分的反应产物:通式为R(OH)n的支化或线型醇,其中R为具有约2至20个碳原子的脂族或环脂族基团(优选烷基),n为至少2且至多约10;包括约30至80mol%、更优选约35至55mol%的具有的碳原子数(碳原子数是指诸如在酸或醇中的总碳原子数)在约C5至C12、更优选约C7至C10之间的线型酸和约20至70mol%、更优选约35至55mol%的至少一种具有的碳原子数在约C5至C13、更优选约C7至C10之间的支化酸的混合酸;其中酯显示下列性能:由改进Sturm试验测量在28天内至少60%生物降解;倾点低于-25℃;在-25℃时的粘度低于7500cps。
在最优选的实施方案中,需要具有包括多种异构体、更优选多于3种异构体、最优选多于5种异构体的支化酸。线型酸优选为具有通式RCOOH的烷基单或二羧酸,其中R为约4至11个碳原子,更优选约7至10个碳原子的正烷基。用于形成可生物降解合成酯基本原料的不大于10%的支化酸含有季碳原子也是优选的。
这些可生物降解合成基本原料特别适用于形成可生物降解润滑剂,如双循环发动机油、可生物降解弹射器油、可生物降解液压油、可生物降解钻孔液体、可生物降解水轮机油、可生物降解润滑脂、可生物降解压缩机油和需要或希望生物降解的功能性油和其它工业和发动机应用。
根据本发明配制的可生物降解润滑剂包括约60至99wt%的至少一种上述可生物降解合成基本原料,约1至20wt%的润滑剂添加剂体系,和约0至20wt%的溶剂。优选实施方案的描述
根据本发明用于配制各种可生物降解润滑剂和油的支化合成酯基本原料优选由工业级季戊四醇与约30-70mol%的C8和C10线型酸(“C810”线型酸)和约30-70mol%的异-C8(例如Cekanoic 8)支化酸的反应产物形成,所述季戊四醇包括约86-92%的单-季戊四醇,6-12%的二-季戊四醇和1-3%的三-季戊四醇。
新戊二醇(NPG)可用2-乙基己酸或异-C8酸完全支化并仍然保持约90%的可生物降解性(通过改进Sturm试验测量)。当将两种支化酸加入支化多醇中后,酯键在支化醇的季碳原子周围变得拥挤。加入支化醇中的另一些支化酸开始降低分子的可生物降解性能,以致于通过将支化酸第四次加入支化醇中,所得分子的生物降解性能由80%降至低于15%(通过改进Sturm试验测量)。
将线型酸加入分子中可消除支化醇的季碳原子周围的空间拥挤。因此例如通过在季戊四醇上具有两种支化酸和两种线型酸,酶可进入酯键中,因此可发生生物降解的第一阶段,即酯的水解。对于各种季戊四醇酯,羟基被各种支化和线型酸酯化。醇
可与本发明的支化和线型酸反应的醇中,可列举如下通式表示的多醇(即多羟基化合物):
R(OH)n其中R为脂族或环脂族烃基(优选烷基),n至少为2。烃基可含约2至约20或更多个碳原子,且烃基还可含取代基如氯、氮和/或氧原子。多羟基化合物通常含有约2至约10个羟基,更优选约2至约6个羟基。多羟基化合物还可含一个或多个氧亚烷基,因此,多羟基化合物包括诸如聚醚多醇类化合物。在用于形成羧酸酯的多羟基化合物中所含的碳原子数(即碳的个数)和羟基基团数(即羟基个数)可在宽范围内变化。
下列醇特别适合用作多醇: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、单-季戊四醇、工业级季戊四醇、二-季戊四醇、乙二醇、丙二醇和聚亚烷基二醇(如聚乙二醇、聚丙二醇、聚丁二醇等,及其共混物如乙二醇与丙二醇的聚合混合物。)
优选的支化或线型醇选自:工业级季戊四醇、单-季戊四醇、二-季戊四醇、新戊二醇、三羟甲基丙烷、三羟甲基乙烷和丙二醇、1,4-丁二醇、山梨(糖)醇等,及2-甲基丙二醇。最优选的醇为工业级(即88%单、10%二和1-2%三)季戊四醇。支化酸
支化酸优选为具有碳原子数在约C5至C13更优选C7至C10之间的单羧酸,其中优选支链是甲基。优选的支化酸是其中低于或等于10%的支化酸含季碳原子的那些支化酸。该单羧酸为至少一种选自2-乙基己酸、异-庚酸、异-辛酸、异-壬酸、异-癸酸和α-支化酸的酸。最优选的支化酸为异-辛酸,如Cekanoic 8酸。
需要具有包括多种异构体,优选多于3种异构体,更优选多于5种异构体的支化酸。线型酸
优选的线型单-和/或二羧酸是具有约5至12,优选7至10个碳原子的任何线型饱和烷基羧酸。最优选的线型酸是单羧酸。
线型酸的一些例子包括正-庚酸、正辛酸、正癸酸和正壬酸。选取的二酸包括己二酸、壬二酸、癸二酸和十二烷二酸。为改进所得酯产品的粘度,总酸混合物的至多20wt%可由线型二酸组成。可生物降解的润滑剂
支化合成酯基本原料可与选择的润滑剂添加剂一起配制可生物降解润滑剂。下面所列的添加剂通常以提供正常附加功能的量使用。各组分的一般用量也在下面列出。优选的可生物降解润滑剂含有约80wt%或更多的基本原料和20wt%的下列各种并用添加剂。
(宽范围) (优选)
wt% wt%粘度指数改进剂 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去垢剂和防锈剂 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密封溶涨剂 0.1-8 0.1-4摩擦改进剂 0.01-3 0.01-1.5可生物降解合成酯基本原料 ≥80% ≥80%
当使用其它添加剂时,需要(尽管不是必须的)制备包括分散剂(按所述浓缩量)与一种或多种其它添加剂(当构成添加剂混合物时,这里将其浓缩物称为添加剂体系)的浓缩溶液或分散液,这样可将几种添加剂同时加入基本原料中形成润滑油组合物。添加剂浓缩物在润滑油中溶解可通过溶剂和通过伴随轻微加热混合进行,但这不是必需的。当将添加剂体系与预定量基料润滑剂或基本原料混合时,通常将浓缩物或添加剂体系配制成含有合适量的分散剂添加剂和非必要的另一些添加剂以在最终配料中提供所需的浓度。因此,本发明的可生物降解润滑剂通常可使用至多约20wt%添加剂体系,余量为可生物降解酯基本原料和/或溶剂。
这里表示的所有重量百分比(除非另有说明)都按添加剂的活性成分(A.I.)含量,和/或按各种添加剂体系的总重量,或配料(它是各添加剂的A.I重量加上总油或稀释剂重量之和)计。
用于本发明的上述添加剂在下面的文献中给出(这些文献在这里作为参考引入):US 5,306,313(Emert等人),1994年4月26日授权;US5,312,554(Waddoups等人),1994年5月17日授权;US5,328,624(Chang),1997年7月12日授权;Benfaremo和Liu的论文“曲轴箱发动机油添加剂”,润滑(Lubricativon),Texaco Inc.,pp.1-7;Liston等人,“发动机润滑剂添加剂,它们是什么和它们如何发挥作用”,润滑工程(Lubrication engineering),1992年5月,pp.389-397。
粘度改性剂赋予润滑油高温和低温操作性并使其在高温下保持剪切稳定性,同时在低温下也显示可接受的粘度和流动性。这些粘度改进剂通常为包括聚酯的高分子量烃聚合物。这些粘度改进剂还可被衍生化以包括其它性能或作用,如增加分散性能。合适的粘度改进剂的代表性例子为本领域已知的任何类型,包括聚异丁烯、乙烯与丙烯的共聚物、聚甲基丙烯酸酯、甲基丙烯酸酯共聚物、不饱和二羧酸与乙烯基化合物的共聚物、苯乙烯与丙烯酸酯的共聚物,和部分氢化的苯乙烯/异戊二烯、苯乙烯/丁二烯和异戊二烯/丁二烯共聚物,以及部分氢化的丁二烯和异戊二烯均聚物。
腐蚀抑制剂(又称为抗蚀剂)可减少被润滑油组合物接触的金属部分的降解。腐蚀抑制剂的说明性例子是磷硫化的烃和通过磷硫化烃与碱土金属氧化物或氢氧化物优选在烷基化的苯酚或烷基苯酚硫酯存在下,同样优选在烷基化苯酚或烷基苯酚硫酯存在下,和同样优选在二氧化碳存在下反应获得的产物。磷硫化烃通过合适的烃如萜烯、C2至C6烯烃聚合物如聚异丁烯的重油馏分与5至30wt%磷的硫化物在温度约66至316℃下反应1/2至15小时制备。磷硫化烃的中和可通过US1,969,324中公开的方式进行。
氧化抑制剂或抗氧剂可减少矿物油在使用期间变质的趋势,这种变质可通过氧化产物如淤浆或金属表面上类似清漆的淀积物,和通过粘度增长证实。此类氧化抑制剂包括优选具有C5至C12烷基侧链的烷基酚硫酯的碱土金属盐如壬基酚硫化钙、辛基苯基硫化钡,二辛基苯胺、苯基α-萘基胺、磷硫化或硫化烃等。
摩擦改进剂起到使润滑油组合物如自动变速器用油具有合适摩擦特性的作用。合适的摩擦改进剂的代表性例子是脂肪酸酯和酰胺,聚异丁烯基丁二酸酐-氨基醇的钼配合物,二聚脂肪酸的甘油酯,链烷膦酸盐,与油酰胺的膦酸酯,S-羧基亚烷基烃基丁二酰亚胺,N(羟烷基)链烯基丁二酰胺酸或丁二酰亚胺,二-(低级烷基)亚磷酸酯和环氧化物,及磷硫化N(羟烷基)链烯基丁二酰亚胺的烯化氧加合物。最优选的摩擦改进剂是丁二酸酯或其金属盐,烃基取代丁二酸或酸酐的金属盐和硫连双链烷醇。
分散剂使在使用期间因氧化形成的油不溶物在流体中保持为悬浮状态,由此防止淤浆絮凝和沉淀或淀积于金属部件上。合适的分散剂包括高分子量烷基丁二酰亚胺,油溶性聚异丁烯丁二酸酐与1,2-亚乙基胺类如四亚乙基五胺的反应产物及其硼酸盐。
倾点下降剂(又称为润滑油流动改进剂)可降低流体流动或可被倾倒的温度。这些添加剂是公知的。用于优化流体的低温流动性的那些典型添加剂是富马酸C8至C18二烷基酯-乙酸乙烯酯共聚物,聚甲基丙烯酸酯或石蜡(wax naphthalene)。可通过聚硅氧烷类消泡剂如硅油和聚二甲基硅氧烷控制泡沫。
抗磨损剂,正如它们的名称暗示的,可降低金属部件的磨损。常规抗磨损剂的代表为二烷基二硫代磷酸锌和二芳基二硫代磷酸锌。
消泡剂用于控制润滑剂中的泡沫。泡沫控制可通过高分子量二甲基硅氧烷和聚醚提供。聚硅氧烷类消泡剂的一些例子是硅油和聚二甲基硅氧烷。
去垢剂和金属防锈剂包括磺酸、烷基苯酚、硫化烷基酚、烷基水杨酸、环烷酸和其它油溶性单-或二羧酸的金属盐。高碱性(即过度碱化的)金属盐如高碱性碱土金属磺酸盐(特别是Ca和Mg盐)通常用作去垢剂。
密封溶涨剂包括促使发动机密封剂溶涨的矿物油类,包括8至13个碳原子的脂族醇如十三烷醇,优选的密封溶涨剂是(例如)US 3,974,081(这里作为参考引入)中描述的具有10至60个碳原子和2至4个酯键的油溶性饱和脂族或芳族烃酯,如邻苯二甲酸二己酯。可生物降解的双循环发动机油
支化合成酯基本原料可与选取的润滑剂添加剂用于配制可生物降解的双循环发动机油。优选的可生物降解的双循环发动机油通常用根据本发明形成的可生物降解合成酯基本原料与任何常规双循环发动机油添加剂体系一起配制。下面所列的添加剂通常以提供其常规附加功能的量使用。添加剂体系可包括但不限于粘度指数改进剂、腐蚀抑制剂、氧化抑制剂、偶联剂、分散剂、耐极高压添加剂、着色稳定剂、表面活性剂、稀释剂、去垢剂和防锈剂、倾点下降剂、消泡剂和抗磨损剂。
本发明的可生物降解双循环发动机油通常可使用约75至85%的基本原料,约1至5%的溶剂和余量的包括添加剂体系的其它物质。
用于可生物降解润滑剂的上述添加剂的例子列于如下文献中:US4,663,063(Davis),1987年5月5日授权;US5,330,667(Tiffany,Ⅲ等人),1994年7月19日授权;US4,740,321(Davis等人),1988年4月26日授权;US5,321,172(Alexander等人),1994年6月14日授权;US5,049,291(Miyaji等人),1991年9月17日授权,这些文献这里作为参考引入。可生物降解的弹射器油
弹射器是海洋中的航空母舰上用于将飞机从航空母舰弹射出去的装置。支化合成酯基本原料可与选取的润滑剂添加剂一起用于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通常用根据本发明形成的可生物降解合成酯基本原料与任何常规弹射器油添加剂体系一起配制。下面所列的添加剂通常以提供其常规附加功能的量使用。添加剂体系可包括但不限于粘度指数改进剂、腐蚀抑制剂、氧化抑制剂、耐极高压添加剂、着色稳定剂、去垢剂和防锈剂、消泡剂、抗磨损剂和摩擦改进剂。
本发明的可生物降解弹射器油通常可使用约90至99%的基本原料,和余量的包括添加剂体系的其它物质。
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。若需要,弹射器油可含有其它常规添加剂,如消泡剂、抗磨损剂、其它抗氧剂、耐极高压添加剂、摩擦改进剂和其它水解稳定剂。这些添加剂公开于Klamann,“润滑剂和相关产品”,Verlag Chemie,Deerfield Beach,FL,1984中,这里作为参考引入。可生物降解的液压油
支化合成酯基本原料可与选取的润滑剂添加剂一起用于配制可生物降解的液压油。优选的可生物降解的液压油通常用根据本发明形成的可生物降解合成酯基本原料与任何常规液压油添加剂体系一起配制。下面所列的添加剂通常以提供其常规附加功能的量使用。添加剂体系可包括但不限于粘度指数改进剂、腐蚀抑制剂、边界润滑添加剂、抗乳化剂、倾点下降剂和消泡剂。
本发明的可生物降解液压油通常可使用约90至99%的基本原料,和余量的包括添加剂体系的其它物质。
其它添加剂公开于1988年11月8日授权的US4,783,274(Jokinen等人)中,这里作为参考引入。可生物降解的钻孔液体
支化合成酯基本原料可与选取的润滑剂添加剂一起用于配制可生物降解的钻孔液体。优选的可生物降解的钻孔液体通常用根据本发明形成的可生物降解合成酯基本原料与任何常规钻孔液体添加剂体系一起配制。下面所列的添加剂通常以提供其常规附加功能的量使用。添加剂体系可包括但不限于粘度指数改进剂、腐蚀抑制剂、润湿剂、水流失改进剂、杀菌剂和钻头润滑剂。
本发明的可生物降解钻孔液体通常可使用约60至90%的基本原料,约5至25%的溶剂和余量的包括添加剂体系的其它物质。参见1983年5月3日授权的US4,382,002(Walker等人),这里作为参考引入。
合适的烃溶剂包括:矿物油,特别是那些沸点为200-400℃的具有良好氧化稳定性的石蜡基油,如Mentor 28,由美国埃克森化学公司(ExxonChemical Americas),Houston,Texas销售;柴油和汽油;及重质芳族石脑油。可生物降解的水轮机油
支化合成酯基本原料可与选取的润滑剂添加剂一起用于配制可生物降解的水轮机油。优选的可生物降解的水轮机油通常用根据本发明形成的可生物降解合成酯基本原料与任何常规水轮机油添加剂体系一起配制。下面所列的添加剂通常以提供其常规附加功能的量使用。添加剂体系可包括但不限于粘度指数改进剂、腐蚀抑制剂、氧化抑制剂、增稠剂、分散剂、抗乳化剂、着色稳定剂、去垢剂和防绣剂以及倾点下降剂。
本发明的可生物降解水轮机油通常可使用约65至75%的基本原料,约5至30%的溶剂和余量、通常为约0.01至约5.0wt%(按组合物的总重量计)的包括添加剂体系的其它物质。可生物降解的润滑脂
支化合成酯基本原料可与选取的润滑剂添加剂一起用于配制可生物降解的润滑脂。润滑脂中的主组分为增稠剂或胶凝剂,润滑脂配料中的差别经常涉及此组分。除了增稠剂或胶凝剂外,润滑脂的其它性能和特性可受特定润滑基本原料和可使用的各种添加剂影响。
优选的可生物降解的润滑脂通常用根据本发明形成的可生物降解合成酯基本原料与任何常规润滑脂添加剂体系一起配制。下面所列的添加剂通常以提供其常规附加功能的量使用。添加剂体系可包括但不限于粘度指数改进剂、氧化抑制剂、耐极高压添加剂、去垢剂和防锈剂、倾点下降剂、金属钝化剂、抗磨损剂和增稠剂或胶凝剂。
本发明的可生物降解润滑脂通常可使用约80至95%的基本原料,约5至20%的增稠剂或胶凝剂和余量的包括添加剂体系的其它物质。
用于润滑脂配料中的典型增稠剂包括碱金属皂、粘土、聚合物、石棉、炭黑、硅胶、聚脲或铝配合物。皂增稠的润滑脂是最流行的,其中锂和钙皂最常用。简单的皂润滑脂由长链脂肪酸的碱金属盐和12-羟基硬脂酸锂形成,突出的一种皂润滑脂由12-羟基硬脂酸、氢氧化锂一水合物和矿物油形成。配合物皂润滑脂也是普遍使用的,该润滑脂包括有机酸混合物的金属盐。发现目前使用的一种典型的配合物皂润滑脂是由12-羟基硬脂酸、氢氧化锂一水合物、壬酸和矿物油制备的配合锂皂润滑脂。锂皂描述和示例于很多专利中,这些专利包括:US 3,758,407(Harting),1973年9月11日授权;US 3,791,97 3(Gilani),1974年2月12日授权;US 3,929,651(Murray),1975年12月30日授权和US 4,392,967(Alexander),1983年7月12日授权,这些专利这里作为参考引入。
用于润滑脂中的添加剂的描述可在Boner,“现代润滑脂”,1976,第5章(这里作为参考引入)以及列于上述其它可生物降解产品中的添加剂中找到。可生物降解的压缩机油
支化合成酯基本原料可与选取的润滑剂添加剂一起用于配制可生物降解的压缩机油。优选的可生物降解的压缩机油通常用根据本发明形成的可生物降解合成酯基本原料与任何常规压缩机油添加剂体系一起配制。下面所列的添加剂通常以提供其常规附加功能的量使用。添加剂体系可包括但不限于氧化抑制剂、添加剂加溶剂、防锈剂/金属钝化剂、抗乳化剂和抗磨损剂。
本发明的可生物降解压缩机油通常可使用约80至99%的基本原料,约1至15%的溶剂和余量的包括添加剂体系的其它物质。
用于压缩机油的添加剂还公开于1992年10月20日授权的US5,156,759(Culpon,Jr.)中,这里作为参考引入。
实施例1
下面是不具有用作可生物降解润滑剂满意性能的常规酯基本原料。表1和表2所列性能如下测定。倾点用ASTM # D-97测定。在-25℃下的Brookfield粘度用ASTM # D-2983测定。运动粘度(@40和100℃)用ASTM# D-445测定。粘度指数(Ⅵ)用ASTM # D-2270测定。生物降解用改进Sturm试验(OCED Test No.301B)测定。与分散剂的溶解性通过共混所需比例并观察雾度、浊度、两相等测定。发动机磨损用NMMA Yamaha CE50S润滑性试验测定。氧化诱导时间用分别具有220℃和500psi(3.445Mpa)空气的等温/等压条件的高压差示扫描量热计(HPDSC)测定。水生毒性用分散体水生毒性试验测定。酸值用ASTM # D-664测定。相应样品的羟值用红外光谱测定。
表1 *与分发动机基本原料 倾点 -25℃ 40℃ 100℃ %Bio 散剂的磨损
(℃) (cPs) (cSt) (cSt) 溶解性天然油菜籽油 0 固体 47.80 10.19 86.7 n/a n/a全线型酯己二酸二-十一基酯 +21 固体 13.92 2.80 n/a n/a n/a多醇w/线型&半线型酸TPE/C810 n/a 固体 29.98 5.90 n/a n/a n/a/C7酸TPE/DiPE -45 1380 24.70 5.12 82.31 H 失败/n-C7TPE/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 失败支化己二酸酯己二酸二-十三基酯 -62 n/a 26.93 5.33 65.99 C 失败全支化TPE/异-C8酸 -46 n/a 61.60 8.2 13.33 C n/a*表示与分散剂的溶解性:H=雾浊;C=透明。**表示这种生物降解物质包括15.5wt%的分散体。n/a表示得不到信息。TPE表示工业级季戊四醇。TMP表示三羟甲基丙烷。C810表示正辛酸和正癸酸为主的混合物,并可包括少量n-C6至n-C12酸。C810酸的一个典型例子可包括,例如3-5%n-C6,48-58%n-C8,36-42%n-C10和0.5-1%n-C12。n-C7,8,10表示具有7、8和10个碳原子的线型酸如37mol%n-C7酸、39mol%C8酸、21mol%C10酸和3mol%C6酸的共混物。C7表示通过己烯-1的钴催化氧化反应生产的C7酸,它是70%线型和30%α-支化酸的混合物。其组成大约包括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。
将本发明的支化酯基本原料的性能与各种常规生物降解润滑剂基本原料进行对比,结果在下表2中给出:
表2性能 TPE/Ck8/C 菜籽油 DTDA TMP/iC18
810倾点(℃) -45 0 -54 -20闪点(℃) 274 162 221 n/a-25℃粘度(cps) 3600 固体 n/a 358,00040℃粘度(cSt) 38.78 47.80 26.93 78.34100℃粘度(cSt) 6.68 10.19 5.33 11.94粘度指数 128 208 135 147氧化诱导时间* 15.96 2.12 3.88 4.29润滑性能 通过 n/a 失败 通过(Yamaha发动机)%生物降解 ~85% ~85% ~60% ~65%(改进Sturm)毒性(LC50,ppm) >5000 >5000 <1000 n/a与分散剂的溶解性 可溶解 n/a 可溶解 n/a酸值(mg KOH/g)0.01 0.35 0.04 1.9羟值(mg KOH/g)1.91 n/a 1.49 n/a*氧化诱导时间为用高压差示扫描量热计(HPDSC)测定分子在特定条件下氧化分解的时间值(分钟)。所需的时间越长(分钟数越大),分子越稳定。这证明本发明的分子比目前使用的任何物质氧化稳定性几乎高四倍。用于评估这些分子的条件是:220℃和500psi(3.447Mpa)空气。~表示大约值。>表示大于。<表示小于。DTDA表示己二酸二-十三癸基酯。TMP/iC18表示三羟甲基丙烷与异硬脂酸的三酯。TPE表示工业级季戊四醇。TMP表示三羟甲基丙烷。C810表示3-5%n-C6,48-58%n-C8,36-42%n-C10和0.5-1%n-C12酸的混合物。Ck8表示Cekanoic-8酸,它包含26wt%3,5-二甲基己酸、19wt%4,5-二甲基己酸、17%3,4-二甲基己酸、11wt%5-甲基庚酸、5wt%4-甲基庚酸和22wt%混合甲基庚酸和二甲基己酸的混合物。
上述表2中所列的数据证明,本发明的TPE/C810/Ck8可生物降解酯基本原料其冷流性能和稳定性优于菜籽油。这些数据还证明TPE/C810/Ck8可生物降解酯基本原料其稳定性、可生物降解性和水生毒性优于己二酸二-十三烷基酯。本发明的酯基本原料其冷流性、稳定性和可生物降解性优于TMP/异-C18。
天然产物菜籽油是高度可生物降解的。但它具有非常差的低温性能,并且因其不稳定性不能很好地润滑。菜籽油极不稳定,在发动机中分解导致形成淀积物、淤渣和腐蚀性问题。己二酸二-十一烷基酯,尽管可生物降解,但同样具有非常差的低温性能。低分子量线型酸的多醇酯不能提供润滑性,而高分子量线型或半线型酸的那些多醇酯具有不良低温性能。此外,线型酸的季戊四醇酯与聚酰胺分散剂不相溶。己二酸二-十三烷基酯仅勉强可生物降解,并且当与具有低生物降解性能的分散剂共混时,配料油仅约45%可生物降解。此外,己二酸二-十三烷基酯不能提供润滑性能。低分子量支化己二酸酯如己二酸-二异癸基酯,尽管更可生物降解,但也不能提供润滑性能并且造成密封溶涨问题。三羟甲基丙烷或季戊四醇与支化含氧酸的多醇酯因其前面讨论的空间位阻,因此不容易生物降解。
实施例2
本发明人已发现,可通过将支化酸结合入酯分子中获得具有良好冷流性能、与分散剂的良好溶解性和良好润滑性能的高度可生物降解基本原料。下表3所列的数据证明,所需基本性能尤其可用结合20至70%高度支化含氧酸和30至80%线型酸的多醇酯获得。
表3
倾点 粘度
粘度
粘度
*与分散 发动机基本原料 (℃) -25℃ 40℃ 100℃ %Bio 剂的溶解 磨损
(cPs) (cSt) (cSt) 性TPE/C810/Ck8 -36** 7455** 34.87 6.37 99.54 C 通过TPE/C810/Ck8和TMP/n -56 610 24.90 5.10 81.0 C 通过7,8,10***TPE/C810/Ck8和TPE/1770**** -46 910 30.48 5.75 85.5 H 通过* 表示与分散剂的溶解性:H=雾浊;C=透明。** 表示基本原料与分散剂的倾点或-25℃粘度。*** 表示50∶50重量%比的TPE/C810/Ck8和TMP/7810。**** 表示50∶50重量%比的TPE/C810/Ck8和TPE/1770。1770表示n-C7酸(70%)和α-支化C7酸(30%)的70∶30混合物。其组成大约包括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。TPE表示工业级季戊四醇。TMP表示三羟甲基丙烷。C810表示3-5%n-C6,48-58%n-C8,36-42%n-C10和0.5-1%n-C12酸的混合物。Ck8表示Cekanoic-8酸。它包含26wt%3,5-二甲基己酸、19wt%4,5-二甲基己酸、17%3,4-二甲基己酸、11wt%5-甲基庚酸、5wt%4-甲基庚酸和22wt%混合甲基庚酸和二甲基己酸的混合物。n-C7,8,10表示具有7、8和10个碳原子的线型酸如37mol%n-C7酸、39mol%C8酸、21mol%C10酸和3mol%C6酸的共混物。
上述表3的数据证明,工业级季戊四醇、异-C8和线型C810酸的多醇酯可单独或与其它低分子量酯结合用作可生物降解润滑剂。对于很多可生物降解应用当需要较低的粘度时,这些酯是特别合适的。TPE/C810/Ck8酯可提供足够的润滑性能,甚至当用其它物质稀释时,也可满足润滑性要求无需加入抗磨损添加剂。当需要添加剂如聚异丁烯、EP(极高压)抗磨损添加剂、腐蚀抑制剂或抗氧剂时,会降低最终产品的可生物降解性和增加毒性。若基本原料在无添加剂下提供所需的性能或若所需的添加剂可最大限度地减少,则在这种情况下最终产品反映出基本原料的高生物降解性和低毒性。
实施例3
按照本发明制备酯基本原料的样品,其中将220 1b(99.8kg)C810酸和205 1b(93kg)Cekanoic 8酸(50∶50摩尔比)投入反应器中,并在大气压下加热至430°F(221℃)。然后将75 1b(34kg)工业级季戊四醇加入该酸混合物中并降低压力至开始排出水。将水从塔顶排出以加快反应进行。约6小时反应时间后,将过量的酸从塔顶除去直至反应产品达到0.26mgKOH/g的总酸值。然后将产品在90℃下用两倍化学计量的Na2CO3(按酸值计)和0.15wt%的混合物(按反应器中的量计)中和和脱色2小时。该混合物为80wt%炭黑和20wt%dicalite的掺混物。在90℃下2小时后,将产品进行真空过滤除去固体。
对产品测量下表4中所列的性能。
表4总酸值 0.071mgKOH/g比重 0.9679倾点 -45℃ppm水 97闪点(COC) 285℃氧化诱导时间(分钟) 15.96粘度
-25℃ 3950cps粘度
40℃ 38.88cSt粘度
100℃ 6.66cSt粘度指数 127
对产品进行酸分析(皂化)确定每一分子上各种酸的实际量。下表5列出了对于产品酯各种酸的量。
表5Cekanoic 8酸 43.35%n-C8酸 35.73%n-C10酸 20.92%
将所得酯产品进行和不进行添加剂处理,进行应用于液压油中的生物降解试验。添加剂以2-5wt%的处理比例使用。结果在下表6中给出。
表6产品 %生物降解 标准偏差 满足10天时限TPE/C810/Ck8(单独) 92.9 ±7.0 是TPE/C810/Ck8+BIO SHP Adpack* 80.5 ±1.6 不TPE/C810/Ck8+MGG Adpack*** 75.4 ±6.9 不TPE/C810/Ck8+Synestic 76.8 ±14.7 不Adpack*** 表示埃克森公司(Exxon Company),USA出售的润滑剂添加剂体系,商标为Univis BIO SHP Adpack。** 表示埃克森公司,Paramins出售的润滑剂添加剂体系,商标为Synestic Adpack。*** 表示埃克森公司,USA出售的润滑剂添加剂体系,商标为MGG Adpack。
将按照实施例3形成的酯基本原料也以50∶50wt%的比例与酯TMP/7810共混。将共混物进行和不进行添加剂处理进行应用于双循环发动机油中的生物降解试验。添加剂以14-16wt%的处理比例使用。结果在下表7中给出。
表7产品 %生物降解 标准偏差TPE/C810/Ck8+TMP/7810(50∶50) 80.7 ±3.6TPE/C810/Ck8+TMP/7810+14.5wt%分散剂* 76.1 ±4.6* 分散剂体系主要包括聚酰胺。
实施例4
下表8给出全线型和半线型酯与根据本发明形成的生物降解合成酯基本原料的对比数据。我们提供本发明酯基本原料的两个实施例,因为它们含有两种不同摩尔比的Cekanoic 8和C810。结果表明一定量的支化不会对可生物降解性能造成很大影响(通过改进Sturm试验测量),并且事实上与常识相反实际还提高了可生物降解性。
表8酯 %生物降解(28天) 标准偏差 10天时限全线型酯
TMP/7810 76.13 8.77 不
TPE/Di-PE/n-C7 82.31 6.25 是
L9己二酸酯 89.63 6.28 是
MPD/AA/C810 86.09 3.76 是半线型酯
TMP/异硬脂酸酯 63.32 1.91 不
TMP/1770 76.46 1.58 不
TMP/1770 83.65 6.89 不支化酯
TPE/C810/Ck8* 92.90 7.00 是
TPE/C810/Ck8** 99.54 1.85 是注:TMP/7810表示三羟甲基丙烷与C7、C8和C10酸的三酯。
TPE/Di-PE/n-C7表示工业级季戊四醇、二季戊四醇与n-C7酸的酯。
L9己二酸酯表示己二酸与n-C9醇的二酯。
MPD/AA/C810表示2-甲基-1,3-丙二醇(2mol)、己二酸(1mol)及n-C8和n-C10酸(2mol)的复合酯。
菜籽油为甘油与硬脂酸的三酯。
TMP/异硬脂酸表示三羟甲基丙烷与异硬脂酸(每个酸链有1个甲基支链)的三酯。
TMP/1770表示三羟甲基丙烷与n-C7酸(70%)和α-支化C7酸(30%)的70∶30混合物的三酯。1770的组成大约包括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。
TPE/1770表示工业级季戊四醇与n-C7酸(70%)和α-支化C7酸(30%)的70∶30混合物的酯。1770的组成大约包括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。
* TPE/C810/Ck8表示工业级季戊四醇与45∶55摩尔比的异-C8酸(Ck8)和C810酸的酯。
** TPE/C810/Ck8表示工业级季戊四醇与30∶70摩尔比的异-C8酸(Ck8)和C810酸的酯。
Claims (16)
1.一种可生物降解的合成酯基本原料,它包括如下组分的反应产物:
通式R(OH)n的支化或线型醇,其中R为具有约2至20个碳原子的脂族或环脂族基团,n至少为2;和
包括约30至80mol%的具有的碳原子数在约C5至C12之间的线型酸和约20至70mol%的至少一种具有的碳原子数在约C5至C10之间的支化酸的混合酸;其中用于形成所述可生物降解合成酯基本原料的不大于10%的所述支化酸含有季碳原子;其中所述酯基本原料显示如下性能:由改进Sturm试验测量在28天内至少60%的生物降解性;倾点低于-40℃;在-25℃时的粘度低于7500cps。
2.根据权利要求1的可生物降解合成酯基本原料,其中所述线型酸具有的碳原子数范围为约C7至C10。
3.根据权利要求1的可生物降解合成酯基本原料,其中所述混合酸包括约35至55mol%的线型酸。
4.根据权利要求1的可生物降解合成酯基本原料,其中所述支化酸具有的碳原子数范围为约C7至C10。
5.根据权利要求3的可生物降解合成酯基本原料,其中所述混合酸包括约35至55mol%的所述支化酸。
6.根据权利要求1的可生物降解合成酯基本原料,其中所述支化酸包括多种异构体。
7.根据权利要求6的可生物降解合成酯基本原料,其中所述支化酸包括至少3种异构体。
8.根据权利要求7的可生物降解合成酯基本原料,其中所述支化酸包括约大于3至5种异构体。
9.根据权利要求1的可生物降解合成酯基本原料,其中所述线型酸选自烷基单羧酸或二羧酸。
10.根据权利要求1的可生物降解合成酯基本原料,其中所述线型酸具有通式RCOOH,其中R为具有约4至11个碳原子的直链烷基。
11.根据权利要求1的可生物降解合成酯基本原料,其中所述酯还显示至少175℃的高闪点COC。
12.根据权利要求1的可生物降解合成酯基本原料,其中所述支化或线型醇选自工业级季戊四醇、单-季戊四醇、二-季戊四醇、新戊二醇、三羟甲基丙烷、乙二醇或丙二醇、丁二醇、山梨(糖)醇和2-甲基丙二醇。
13.根据权利要求1的可生物降解合成酯基本原料,其中所述支化酸主要为每分子平均支化度为约0.3至1.9的双支化或α-支化酸。
14.根据权利要求4的可生物降解合成酯基本原料,其中所述支化酸为至少一种选自2-乙基己酸、异-庚酸、异-辛酸、异-壬酸和异-癸酸的酸。
15.根据权利要求1的可生物降解合成酯基本原料,其中所述基本原料在40℃显示至少34.87cSt的粘度。
16.根据权利要求1的可生物降解合成酯基本原料,其中所述酯基本原料在40℃的黏度为至少34.87cSt。
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- 1995-12-08 AU AU44227/96A patent/AU710121B2/en not_active Ceased
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