CN116601263A - 性能提高的包含烷基化二苯胺的组合物 - Google Patents
性能提高的包含烷基化二苯胺的组合物 Download PDFInfo
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- CN116601263A CN116601263A CN202180077388.3A CN202180077388A CN116601263A CN 116601263 A CN116601263 A CN 116601263A CN 202180077388 A CN202180077388 A CN 202180077388A CN 116601263 A CN116601263 A CN 116601263A
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- Prior art keywords
- composition
- iii
- diphenylamines
- alkylated
- alkylated diphenylamines
- Prior art date
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Abstract
本发明涉及一种包含结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的组合物，涉及包含烷基化二苯胺的混合物的工业产品，例如添加剂掺和物、发动机油和聚合物组合物，且涉及所述混合物作为例如添加剂掺和物、发动机油和聚合物组合物的工业产品中的添加剂的用途。其中R为支链C4‑C16烷基，且其中按所述组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计，结构式(IV)的四烷基化二苯胺的总量在0.20重量％至3.5重量％范围内。
Description
技术领域
本发明涉及一种包含烷基化二苯胺的化合物。本发明还涉及包含这种组合物的工业产品以及这种组合物作为工业产品中的添加剂的用途。
背景技术
润滑剂(例如用于各种机器中的润滑剂)在存储、运输和使用期间，尤其是当这类润滑剂暴露于极大促进其氧化的高温和铁催化环境时，容易氧化变质。如果不进行控制，这种氧化将促进形成腐蚀性酸性产物、油泥、清漆、树脂和其它不溶于油的产物，并可能导致润滑剂的指定物理和摩擦学特性丧失。因此，一种常见做法是在润滑剂中加入抗氧化剂，以至少在某种程度上预防氧化，以延长其使用寿命。含有各种二芳胺或苯酚化合物作为抗氧化剂的润滑剂组合物在本领域是众所周知的。
WO 2007/100726 A2揭露了一种润滑剂组合物，其包含：至少一种润滑油，其选自由天然和合成润滑基础油组成的群组；至少一种第一抗氧化剂，其可为烷基化二苯胺；以及作为第二抗氧化剂的至少一种含硫烷基化苯酚，其中在向润滑剂补充第一和第二抗氧化剂时，观测到有关氧化稳定性的协同作用。
然而，可以看到这种方法的缺点，即为了提高发动机油的氧化稳定性，必须将一类新的添加剂(即含硫烷基化苯酚)添加到发动机油中，这不仅会再次增加完全完成的发动机润滑剂的复杂度，并且还会增加其生产成本。
此外，发动机油的规格在性能要求方面变得越来越严格，并且正在开发新的配方以满足这些新规格。发动机油中包含的许多添加剂对铅具有腐蚀性。配方设计师很难在同样满足铅腐蚀规格的同时通过采用某些有益添加剂来满足当前的发动机油规格。举例来说，配方发动机油中引起铅腐蚀的某些组分包括某些洗涤剂、抗磨添加剂、摩擦改进剂和抗氧化剂。许多此类所需添加剂化学物质由于导致发动机油制剂不符合铅腐蚀限制的行业规格而被取消了使用资格。
WO 2004/015043 A1揭露一种发动机油，其包含某些对铅尤其不具有侵蚀性的1,2,4-三唑金属减活剂。然而，也必须看到这种方法的缺点，即必须将一种更复杂的化学添加剂添加到发动机油中，所述发动机油通常已包含复杂的添加剂混合物，例如抗氧化剂、抗磨添加剂、分散剂、洗涤剂、防泡沫添加剂、粘度指数改进剂、铜钝化剂、防锈剂、降凝剂、破乳剂和摩擦改进剂。因此，这种方法不仅会增加完全完成的发动机润滑剂的复杂度，而且还会增加其生产成本。
发明内容
技术问题
因此，本发明的一个目标是克服与用于提高工业产品(例如发动机油)性能的组合物相关的背景技术缺点，尤其是在所述组合物的氧化稳定性方面，且优选地同样在所述组合物针对铅腐蚀的抗性方面。
特别是，本发明的目标是提供一种组合物，所述组合物在作为单独的添加剂或作为所谓的“添加剂包”中的组分添加到基础油中以形成完全完成的发动机油，或所述组合物提高发动机油的性能，尤其是在氧化稳定性方面且优选地同样在针对铅腐蚀的抗性方面。
更优选的是，本发明的目标是提供一种组合物，所述组合物在作为单独的添加剂或作为添加剂包中的组分添加到基础油中以形成完全完成的发动机油时，或者在已经以完全完成的发动机油的形式存在时，可产生高氧化稳定性和对铅腐蚀的良好抗性的有利性能组合。
技术的解决方案
独立权利要求对至少部分地解决上述目标中的至少一个，优选一个以上目标做出了贡献。从属权利要求提供提供有助于至少部分解决至少一个所述目标的优选实施例。
对解决本发明的至少一个所述目标是通过组合物的实施例1做出的，所述组合物包含结构式(I)、(II)、(III)和(IV)的烷基化二苯胺：
其中R为支链C4-C16烷基，且其中结构式(IV)的四烷基化二苯胺的总量在0.20重量％至3.5重量％范围内，更优选地在0.21重量％至3.3重量％范围内，且甚至更优选地在0.22重量％至3.1重量％范围内，在各情况下按组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量计。
结构式(I)、(II)、(III)和(IV)中连接到残基R的线指示这个残基R可连接到苯环的任一碳原子(即邻位、间位或对位)。因此，结构式(I)的烷基化二苯胺表示单取代的二苯胺衍生物，结构式(II)的烷基化二苯胺表示二取代的二苯胺衍生物，结构式(III)的烷基化二苯胺表示三取代的二苯胺衍生物，且结构式(IV)的烷基化二苯胺表示四取代的二苯胺衍生物。
用于润滑剂的包含结构式(I)、(II)和(III)的烷基化二苯胺的混合物的添加剂根据现有技术已知。所述添加剂用作抗氧化剂以改进润滑剂(例如发动机油)的氧化稳定性。然而，现在令人惊奇地发现，通过确保这些组合物包含明确限定量的具有结构式(IV)的四烷基化二苯胺，可以实现包含这种添加剂的发动机油在氧化稳定性方面的性能提高。特别令人惊讶的是，通过确保这些组合物包含明确限定量的四烷基化二苯胺，还可以提高针对铅腐蚀的抗性。
根据本发明的组合物可通过以下制备：提供具有结构式(I)、(II)和(III)的烷基化二苯胺的混合物；以及向所述混合物补充所需量的具有结构式(IV)的四烷基化二苯胺。
用于产生具有结构式(I)、(II)和(III)的烷基化二苯胺的方法例如揭露于US 6,315,925B1中。此处，二苯胺在酸性粘土作为催化剂的情况下与烯烃反应。对于制备优选的壬基烷基化二苯胺，其中R表示具有式-C9H19的支链残基，二苯胺可在按二苯胺计2.0重量％至25.0重量％的酸性粘土存在下且在反应混合物中不存在无机或有机酸的情况下用过量的壬烯或异构壬烯的混合物烷基化，如例如US 6,315,925 B1的实例1中所展示。
具有结构式(IV)的烷基化二苯胺(例如四壬基二苯胺)可以通过使二苯胺与过量的烯烃(例如在四壬基二苯胺的情况下与壬烯)在大气压力下在140℃与155℃之间的反应温度下反应4周的反应时间来产生。从由此获得的包含单取代、二取代、三取代和四取代二苯胺的反应混合物中，可以例如通过蒸馏进一步富集具有结构式(IV)的四取代二苯胺。借助于由此获得的包含富集含量的具有结构式(IV)的烷基化二苯胺的蒸馏份，这种异构体在给定的具有结构式(I)、(II)和(III)的烷基化二苯胺的混合物中的含量可以通过向所述给定混合物中添加适当量的所述蒸馏份来调整。
在根据本发明的组合物的实施例2中，所述组合物是根据其实施例1进行设计，其中结构式(I)的单烷基化二苯胺的总量在10重量％至35重量％范围内，更优选地在13重量％至30重量％范围内，且甚至更优选地在16重量％至25重量％范围内，在各情况下按组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计。
在根据本发明的组合物的实施例3中，所述组合物是根据其实施例1或2进行设计，其中结构式(II)的二烷基化二苯胺的总量在60重量％至85重量％范围内，更优选地在65重量％至82重量％范围内，且甚至更优选地在70重量％至79重量％范围内，在各情况下按组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计。
在根据本发明的组合物的实施例4中，所述组合物是根据其实施例1至3中的任一个进行设计，其中结构式(III)的三烷基化二苯胺的总量在1重量％至10重量％范围内，更优选地在2重量％至8重量％范围内，且甚至更优选地在3重量％至6重量％范围内，在各情况下按组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计。
在根据本发明的组合物的实施例5中，所述组合物是根据其实施例1至4中的任一个进行设计，其中所述组合物包含少于1重量％、优选地少于0.5重量％、且更优选地少于0.1重量％的具有结构式C12H11N的非烷基化二苯胺，在各情况下按组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计。
在根据本发明的组合物的实施例6中，所述组合物是根据其实施例1至5中的任一个进行设计，其中残基R为具有1至20个碳原子的烷基，其可为支链或直链的，例如甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、前述各者的异构体(例如叔丁基、2-乙基己基和其类似基团)以及前述各者的混合物。
在根据本发明的组合物的实施例7中，所述组合物是根据其实施例6进行设计，其中残基R为具有式-C9H19的支链烷基。
在根据本发明的组合物的实施例8中，所述组合物是根据其实施例7进行设计，其中除了结构式(I)、(II)、(III)和(IV)的烷基化二苯胺以外，所述组合物还包含少于1重量％、优选地少于0.5重量％、且甚至更优选地少于0.1重量％的携带至少一个烷基R'的烷基化二苯胺，所述烷基R'不为具有式-C9H19的支链烷基，在各情况下按组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计。
在根据本发明的组合物的实施例9中，所述组合物是根据其实施例1至8中的任一个进行设计，其中满足以下条件(α1)至(α7)中的至少一个，优选地所有以下条件(α1)至(α6)：
(α1)所述组合物的运动粘度(cinematic viscosity)(根据ASTM D 445在40℃的温度下测定)在100至1000cSt范围内，更优选地在200至900cSt范围内，且更优选地在450至650cSt范围内；
(α2)所述组合物的加德纳色度(Gardner colour)(根据ASTM D 1544测定)小于15加德纳(Gardner)，优选地小于10加德纳，且更优选地小于5加德纳；
(α3)所述组合物的水含量(根据ASTM E 203测定)少于0.1重量％，优选地少于0.05重量％，且更优选地少于0.01重量％；
(α4)所述组合物的氮含量(根据ASTM D 2896测定)在3.2重量％至3.8重量％范围内，优选地在3.3重量％至3.7重量％范围内，且更优选地在3.4重量％至3.9重量％范围内；
(α5)所述组合物的比重(根据ASTM D 1298在25℃的温度下测定)在0.930至0.980范围内，优选地在0.935至0.975范围内，且更优选地在0.940至0.970范围内；
(α6)所述组合物的总碱值(TBN)(根据ASTM D 2896测定)在125至160mg KOH/g范围内，优选地在130至150mg KOH/g范围内，且更优选地在135至145mg KOH/g范围内。
在根据本发明的组合物的实施例10中，所述组合物是根据其实施例1至9中的任一个进行设计，其中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量，优选地其中R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量为至少98重量％，更优选地为至少98.5重量％，且甚至更优选地为至少99重量％，在各情况下按组合物的总重量计。
在根据本发明的组合物的实施例11中，所述组合物是根据其实施例1至10中的任一个进行设计，其中所述组合物为润滑剂或润滑组合物。
在根据本发明的组合物的实施例12中，所述组合物是根据其实施例11进行设计，其中所述组合物为添加剂掺和物。“添加剂掺和物”(也称为“添加剂母料”或“添加剂包”)是一种用于处理工业和汽车润滑剂的掺和物，其包含不同添加剂的组合，所述添加剂例如抗氧化剂、抗磨添加剂、分散剂、无灰(无金属)聚合物材料、洗涤剂、防泡沫添加剂、粘度指数改进剂、铜钝化剂、防锈剂、降凝剂、破乳剂和摩擦改进剂。根据本发明的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物可由此通过这种添加剂包的一部分组成。
在根据本发明的组合物的实施例13中，所述组合物是根据其实施例12进行设计，其中所述添加剂掺和物包含对铅具有侵蚀性的添加剂，优选地选自由以下组成的群组的添加剂：含硫抗氧化剂、含硫抗磨添加剂、含硫铜钝化剂或植物油衍生的摩擦改进剂。
在根据本发明的组合物的实施例14中，所述组合物是根据其实施例12或13进行设计，其中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量，优选地其中R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量在0.01重量％至30重量％范围内，优选地在0.1重量％至20重量％范围内，且甚至更优选地在0.5重量％至10重量％范围内，在各情况下按添加剂掺和物的总重量计。
在根据本发明的组合物的实施例15中，所述组合物是根据其实施例11进行设计，其中组合物为一种发动机油。
在根据本发明的组合物的实施例16中，所述组合物是根据其实施例15进行设计，其中所述发动机油包含至少一种基础油以及如实施例1至7中所定义，优选地呈如实施例12至14中所定义的添加剂掺和物形式的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物，优选地其中R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物。
在根据本发明的组合物的实施例17中，所述组合物是根据其实施例16进行设计，其中R为支链C4-C16烷基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量，优选地R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量在0.01重量％至5重量％范围内，优选地在0.05重量％至2.5重量％范围内，且甚至更优选地在0.1重量％至1.5重量％范围内，在各情况下按发动机油的总重量计。
在根据本发明的组合物的实施例18中，所述组合物是根据其实施例11进行设计，其中所述组合物为包含聚合物、优选地热塑性聚合物、优选地聚氨酯的聚合物组合物。
在根据本发明的组合物的实施例19中，所述组合物是根据其实施例18进行设计，其中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量，优选地其中R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量在0.01重量％至1.0重量％范围内，优选地在0.05重量％至0.75重量％范围内，且甚至更优选地在0.1重量％至0.5重量％范围内，在各情况下按聚合物组合物的总重量计。
在根据本发明的组合物的实施例20中，所述组合物是根据其实施例18或19进行设计，其中所述热塑性聚合物选自由以下组成的群组：低密度聚乙烯(LDPE)、线型低密度聚乙烯(LLDPE)、中密度聚乙烯(MDPE)、高密度聚乙烯(HDPE)，衍生自C3及以上单烯和二烯不饱和烃单体的均聚物，例如聚丙烯、聚异丁烯、聚甲基丁烯-1、聚甲基戊烯-1、聚丁烯-1、聚异丁烯等；衍生自两种或更多种单体的共聚物，例如优选地至少具有大部分丙烯的乙烯-丙烯共聚物、丙烯-丁烯-1共聚物、丙烯-异丁烯共聚物等及其掺和物、聚苯乙烯；聚卤代乙烯；以及热塑性工程塑料，例如聚酰胺、聚酯、聚苯醚、聚苯硫醚、聚缩醛、脂肪族聚酮共聚物或三聚物、聚(醚砜)、聚碳酸酯、液晶聚合物、聚(醚醚酮)、聚氨酯和聚(芳基化物)。优选地，由根据本发明的组合物保护的热塑性树脂为聚氨酯或聚丙烯。
如果由根据本发明的组合物稳定的热塑性聚合物为聚氨酯，那么根据本发明的组合物可添加至随后与异氰酸酯反应以形成聚氨酯的多元醇中。
还通过以下方式来解决根据本发明的至少一个目标：使用根据其实施例1至10中的任一个的组合物作为工业产品中的添加剂，优选地作为如实施例12至14中所定义的添加剂掺和物的一部分，作为如实施例15至17中所定义的发动机油中的添加剂，或作为如实施例18至20中所定义的聚合物组合物中的添加剂。
实施本发明的最佳方式
根据本发明的添加剂掺和物中的添加剂
根据本发明的添加剂掺和物(或添加剂包)是用于处理工业和汽车润滑剂的掺和物，其除了基础油以外还包含不同添加剂的组合，所述添加剂例如抗氧化剂、抗磨添加剂、分散剂、无灰(无金属)聚合物材料、洗涤剂、防泡沫添加剂、粘度指数改进剂、铜钝化剂、防锈剂、降凝剂、破乳剂和摩擦改进剂。根据本发明的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物，优选地其中R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物可由此通过这种添加剂包的一部分。
除了结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物以外，优选地除了其中R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物以外，添加剂掺和物中可存在的适合抗氧化剂选自：
1)烷基化单苯酚，例如2,6-二叔丁基-4-甲基苯酚、2-丁基-4,6-二甲基苯酚、2,6-二叔丁基-4-乙基苯酚、2,6-二叔丁基-4-正丁基苯酚、2,6-二叔丁基-4-异丁基苯酚、2,6-二环戊基-4-甲基苯酚、2-(α-甲基-环己基)-4,6-二甲基苯酚、2,6-二(十八烷基)-4-甲基苯酚、2,4,6-三环己基苯酚、2,6-二叔丁基-4-甲氧基甲基苯酚、线型或侧支链壬基苯酚(例如2,6-二壬基-4-甲基苯酚)、2,4-二甲基-6-(1'-甲基-十一烷-1'-基)苯酚、2,4-二甲基-6-(1'-甲基十七烷-1'-基)苯酚、2,4-二甲基-6-(1'-甲基十三烷-1'-基)苯酚或其混合物；
2)烷基硫代甲基苯酚，例如2,4-二辛基硫代甲基-6-叔丁基苯酚、2,4-二辛基硫代甲基-6-甲基苯酚、2,4-二辛基硫代甲基-6-乙基苯酚或2,6-二(十二烷基)硫代甲基-4-壬基苯酚；
3)对苯二酚和烷基化对苯二酚，例如2,6-二叔丁基-4-甲氧基-苯酚、2,5-二叔丁基对苯二酚、2,5-二叔戊基对苯二酚、2,6-二苯基-4-十八烷基氧基苯酚、2,6-二叔丁基-对苯二酚、2,5-二叔丁基-4-羟基茴香醚、3,5-二叔丁基-4-羟基茴香醚、3,5-二叔丁基-4-羟基苯硬脂酸酯或己二酸双(3,5-二叔丁基-4-羟基苯基)酯；
4)生育酚，例如α-生育酚、β-生育酚、γ-生育酚或δ-生育酚或其混合物(维生素E)；
5)羟基化硫代二苯醚，例如2,2'-硫代双(6-叔丁基-4-甲基苯酚)、2,2'-硫代双(4-辛基苯酚)、4,4'-硫代双(6-叔丁基-3-甲基苯酚)、4,4'-硫代双(6-叔丁基-2-甲基苯酚)、4,4'-硫代双(3,6-二仲戊基苯酚)或4,4'-双(2,6-二甲基-4-羟基苯基)二硫醚；
6)亚烷基双苯酚，例如2,2'-亚甲基双(6-叔丁基-4-甲基苯酚)、2,2'-亚甲基双(6-叔丁基-4-乙基苯酚)、2,2'-亚甲基双(4-甲基-6-(α-甲基-环己基)-苯酚)、2,2'-亚甲基双(4-甲基-6-环己基苯酚)、2,2'-亚甲基双(6-壬基-4-甲基苯酚)、2,2'-亚甲基双(4,6-二叔丁基苯酚)、2,2'-亚乙基双(4,6-二叔丁基苯酚)、2,2'-亚乙基双(6-叔丁基-4-异丁基苯酚)、2,2'-亚甲基双(6-(α-甲基苯甲基)-4-壬基苯酚)、2,2'-亚甲基双(6-(α,α-二甲基苯甲基)-4-壬基苯酚)、4,4'-亚甲基双(2,6-二叔丁基苯酚)、4,4'-亚甲基双(6-叔丁基-2-甲基苯酚)、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-丁烷、2,6-双(3-叔丁基-5-甲基-2-羟基苯甲基)-4-甲基苯酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷、乙二醇双(丁酸3,3-双(3'-叔丁基-4'-羟基苯基)酯)、双(3-叔丁基-4-羟基-5-甲基苯基)二环戊二烯、对苯二甲酸双(2-(3'-叔丁基-2'-羟基-5'-甲基苯甲基)-6-叔丁基-4-甲基苯基)酯、1,1-双(3,5-二甲基-2-羟基苯基)丁烷、2,2-双(3,5-二叔丁基-4-羟基苯基)丙烷、2,2-双(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基巯基丁烷或1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)-戊烷；
7)O-苯甲基、N-苯甲基和S-苯甲基化合物，例如3,5,3',5'-四叔丁基-4,4'-二羟基-二苯甲醚、4-羟基-3,5-二甲基苯甲基巯基乙酸十八烷酯、4-羟基-3,5-二叔丁基苯甲基巯基乙酸十三烷酯、三(3,5-二叔丁基)胺、二硫代对苯二甲酸双(4-叔丁基-3-羟基-2,6-二甲基苯甲基)酯、双(3,5-二叔丁基-4-羟基-苯甲基)硫醚或3,5-二叔丁基-4-羟基-苯甲基巯基乙酸异辛酯；
8)羟基苯甲基化丙二酸酯，例如2,2-双(3,5-二叔丁基-2-羟基苯甲基)丙二酸二(十八烷基)酯、2-(3-叔丁基-4-羟基-5-甲基苯甲基)-丙二酸二(十八烷基)酯、巯基乙基-2,2-双(3,5-二叔丁基-4-羟基苯甲基)-丙二酸二(十二烷基)酯或丙二酸二(4-(1,1,3,3-四甲基丁基)苯基)-2,2-双(3,5-二叔丁基-4-羟基苯甲基)酯；
9)芳香族羟基苯甲基化合物，例如1,3,5-三(3,5-二叔丁基-4-羟基-苯甲基)-2,4,6-三甲基苯、1,4-双(3,5-二叔丁基-4-羟基苯甲基)-2,3,5,6-四甲基苯或2,4,6-三(3,5-二叔丁基-4-羟基苯甲基)苯酚；
10)三嗪化合物，例如2,4-双辛基巯基-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二叔丁基-4-羟基苯氧基)-1,3,5-三嗪、2,4,6-三(3,5-二叔丁基-4-羟基苯氧基)-1,2,3-三嗪、异氰脲酸1,3,5-三(3,5-二叔丁基-4-羟基苯甲基)酯、异氰脲酸1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苯甲基)酯、2,4,6-三(3,5-二叔丁基-4-羟基苯基乙基)-1,3,5-三嗪、1,3,5-三(3,5-二叔丁基-4-羟基苯基丙酰基)六氢-1,3,5-三嗪或异氰脲酸1,3,5-三(3,5-二环己基-4-羟基苯甲基)酯；
11)苯甲基膦酸酯，例如2,5-二叔丁基-4-羟基苯甲基-膦酸二甲酯、3,5-二叔丁基-4-羟基苯甲基膦酸二乙酯、3,5-二叔丁基-4-羟基苯甲基膦酸二(十八烷基)酯、5-叔丁基-4-羟基-3-甲基苯甲基-膦酸二(十八烷基)酯或3,5-二叔丁基-4-羟基苯甲基膦酸的单乙酯的钙盐；
12)酰基氨基苯酚，例如4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺或N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯；
13)β-(3,5-二叔丁基-4-羟基苯基)丙酸、β-(5-叔丁基)-4-羟基-3-甲基苯基)丙酸、β-(3,5-二环己基-4-羟基苯基)-丙酸、3,5-二叔丁基-4-羟基苯基乙酸或β-(5-叔丁基)-4-羟基苯基))-3-硫杂丁酸与一元醇或多元醇，例如与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、异氰脲酸三(羟基乙基)酯、N,N'-双(羟基乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基-己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三氧杂双环(2.2.2)辛烷、丙三醇的酯，或基于例如椰子油、菜籽油、葵花油或菜油的天然甘油三酯的酯交换产物；
14)β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺，例如N,N'-双(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二胺、N,N'-双(3,5-二叔丁基-4-羟基苯基丙酰基)三亚甲基二胺或N,N'-双(3,5-二叔丁基-4-羟基苯基丙酰基)肼；
15)抗坏血酸(维生素C)；
16)胺类抗氧化剂，例如N,N'-二异丙基-对亚苯基二胺、N,N'-二仲丁基-对亚苯基二胺、N,N'-双(1,4-二甲基戊基)-对亚苯基二胺、N,N'-双(1-乙基-3-甲基-戊基)-对亚苯基二胺、N,N'-双(1-甲基-庚基)-对亚苯基二胺、N,N'-二环己基-对亚苯基二胺、N,N'-二苯基-对亚苯基二胺、N,N'-二(萘-2-基)-对亚苯基二胺、N-异丙基-N'-苯基-对亚苯基-二胺、N-(1,3-二甲基丁基)-N'-苯基-对亚苯基二胺、N-(l-甲基庚基)-N'-苯基-对亚苯基二胺、N-环己基-N'-苯基-对亚苯基二胺、4-(对甲苯磺酰胺基)二苯胺、N,N'-二甲基-N,N'-二仲丁基-对亚苯基二胺、二苯胺、N-烯丙基二苯胺、4-异丙氧基-二苯胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺、N-苯基-2-萘胺、辛基化二苯胺(例如p,p'-二叔辛基二苯胺)、4-正丁基氨基苯酚、4-丁酰基氨基苯酚、4-壬酰基氨基苯酚、4-十二烷酰基氨基苯酚、4-十八烷酰基氨基苯酚、二(4-甲氧基苯基)-胺、2,6-二叔丁基-4-二甲基氨基-甲基苯酚、2,4'-二氨基-二苯基甲烷、4,4'-二氨基-二苯基甲烷、N,N,N',N'-四甲基-4,4'-二氨基-二苯基甲烷、1,2-二((2-甲基-苯基)-氨基)乙烷、1,2-二(苯基氨基)丙烷、(邻甲苯基)双胍、二(4-(1',3'-二甲基-丁基)-苯基)胺、叔辛基化N-苯基-1-萘胺、单烷基化和二烷基化叔丁基/叔辛基二苯胺的混合物、单烷基化和二烷基化壬基二苯胺的混合物、单烷基化和二烷基化十二烷基二苯胺的混合物、单烷基化和二烷基化异丙基/异己基二苯胺的混合物、单烷基化和二烷基化叔丁基二苯胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单烷基化和二烷基化叔丁基/叔辛基吩噻嗪的混合物、单烷基化和二烷基化叔辛基吩噻嗪的混合物、N-烯丙基吩噻嗪、N,N,N',N”-四苯基-1,4-二氨基丁-2-烯、N,N-双(2,2,6,6-四甲基哌啶-4-基)六亚甲基二胺、癸二酸双(2,2,6,6-四甲基哌啶-4-基)酯、2,2,6,6-四甲基哌啶-4-酮或2,2,6,6-四甲基哌啶-4-醇；和
17)脂肪族或芳香族亚磷酸酯、硫代二丙酸或硫代二乙酸的酯或者二硫代氨基甲酸或二硫代磷酸的盐、2,2,12,12-四甲基-5,9-二羟基-3,7,1-三硫杂十三烷或2,2,15,15-四甲基-5,12-二羟基-3,7,10,14-四硫杂十六烷。
适合的抗磨添加剂选自：
1)二烃基二硫代磷酸金属盐，其中金属为铝、铅、锡、锰、钴、镍、锌或铜，但最常见的为锌。锌盐(二烷基二硫代磷酸锌)表示为
其中R和R'独立地表示C1-C20烷基、C3-C20烯基、C5-C12环烷基、C7-C13芳烷基或C6-C10芳基，例如R和R'独立地为C1-C12烷基；和
2)含硫和/或含磷和/或含卤素化合物，例如硫化烯烃和植物油、磷酸三甲苯酯、磷酸三甲酚酯、氯化链烷烃、烷基和芳基二硫醚和三硫醚、磷酸单烷基酯和磷酸二烷基酯的胺盐、甲基磷酸的胺盐、二乙醇氨基甲基甲苯基三唑、二(2-乙基己基)氨基甲基甲苯基三唑、2,5-二巯基-1,3,4-硫杂二唑的衍生物、丙酸乙基((双异丙基氧基硫膦基)硫基)酯、硫代磷酸三苯酯(triphenyl thiophosphate)(硫代磷酸三苯酯(triphenylphosphorothioate))、硫代磷酸三(烷基苯基)酯和其混合物(例如硫代磷酸三(异壬基苯基)酯)、硫代磷酸二苯基单壬基苯酯、硫代磷酸异丁基苯基二苯酯、3-羟基-1,3-硫杂磷烷-3-氧化物的十二烷胺盐、三硫代磷酸5,5,5-三(2-乙酸异辛酯)、2-巯基苯并噻唑的衍生物(例如1-(N,N-双(2-乙基己基)氨基甲基)-2-巯基-1H-1,3-苯并噻唑)或5-辛基二硫代氨基甲酸乙氧基羰酯。
适合的分散剂选自：
1)曼尼希碱(Mannich base)，其为高分子量苯酚、丙炔聚胺和醛(例如甲醛)的缩合反应产物；
2)基于琥珀酸的分散剂，其为烯烃聚合物和琥珀酸酰化剂(酸、酸酐、酯或卤化物)进一步与有机羟基化合物和/或胺反应的反应产物；和
3)高分子量酰胺和酯，例如烃基酰化剂和多羟基脂肪醇(例如甘油、季戊四醇或山梨醇)的反应产物。
通常使用无灰(无金属)聚合物材料作为分散剂，所述材料通常含有与要分散的颗粒缔合的极性官能团连接的油溶性高分子量主链。常用的烃主链材料为烯烃聚合物和共聚物，即乙烯、丙烯、丁烯、异丁烯、苯乙烯；在聚合物的主链中可以并入或不并入另外的官能团。例如胺、醇、酰胺或酯的极性材料经由桥键连接到主链。
适合的洗涤剂选自：有机酸的钙、镁、钡、钠或锂盐，例如磺酸盐、烷基酚盐、硫化烷基酚盐、羧酸盐、水杨酸盐、膦酸盐、硫代膦酸盐和亚膦酸盐。盐可以是中性的，或者可以被例如金属氢氧化物或碳酸盐过碱化。
适合的防泡沫添加剂选自：硅酮油、聚硅氧烷和聚乙二醇醚。
适合的粘度指数改进剂选自：聚异丁烯、乙烯和丙烯的共聚物、聚丙烯酸酯、聚甲基丙烯酸酯、乙烯基吡咯烷酮/甲基丙烯酸酯共聚物、聚乙烯基吡咯烷酮、聚丁烯、烯烃共聚物、苯乙烯/丙烯酸酯共聚物、苯乙烯/异戊二烯共聚物、苯乙烯/异丁二烯共聚物、异戊二烯/丁二烯共聚物和聚醚。
适合的铜钝化剂选自：
1)苯并三唑和其衍生物，例如4-烷基苯并三唑或5-烷基苯并三唑(例如甲苯三唑)和其衍生物、4,5,6,7-四氢苯并三唑、5,5'-亚甲基双苯并三唑；苯并三唑或甲苯三唑的曼尼希碱，例如1-(二(2-乙基己基)氨基甲基)甲苯三唑和1-(二(2-乙基己基)氨基甲基)-苯并三唑；烷氧基烷基苯并三唑，例如1-(壬基氧基甲基)-苯并三唑、1-(1-丁氧基乙基)-苯并三唑或1-(1-环己基氧基丁基)-甲苯三唑；
2)咪唑衍生物，例如4,4'-亚甲基双(2-十一烷基-5-甲基-咪唑)、双((N-甲基)咪唑-2-基)甲醇辛基醚；
3)含硫杂环化合物，例如2-巯基苯并噻唑、2,5-二巯基-1,3,4-噻二唑、2,5-二巯基苯并噻二唑和其衍生物或3,5-双(二(2-乙基己基)氨基甲基)-1,3,4-噻二唑啉-2-酮；和
4)氨基化合物，例如亚水杨基亚丙基二胺、水杨基氨基胍或其盐。
适合的防锈剂选自：
1)非离子型聚氧化烯多元醇和其酯、聚氧化烯苯酚、有机酸、其酯、金属盐、胺盐和酸酐，例如烷基琥珀酸和烯基琥珀酸以及其与醇、二醇或羟基羧酸的偏酯，烷基琥珀酸和烯基琥珀酸、4-壬基苯氧基乙酸、烷氧基羧酸和烷氧基乙氧基羧酸(例如十二烷氧基乙酸、十二烷氧基(乙氧基)乙酸)和其胺盐的偏酰胺，或N-油酰肌氨酸、山梨醇单油酸酯、萘酸铅和烯基琥珀酸酐(例如十二烯基琥珀酸酐)、2-(2-羧乙基)-1-十二烷基-3-甲基甘油和其盐，例如钠盐和三乙醇胺盐；
2)选自以下的含氮化合物：i)脂肪族或环脂肪族伯胺、仲胺和叔胺以及有机酸和无机酸的胺盐，例如油溶性烷基羧酸铵以及1-(N,N-双(2-羟基乙基)氨基)-3-(4-壬基苯氧基)丙-2-醇，或ii)杂环化合物，例如：被取代的咪唑啉或恶唑啉，例如2-十七烯基-1-(2-羟基乙基)-咪唑啉；
3)含磷化合物，例如磷酸的胺盐、磷酸偏酯或膦酸偏酯或者二烷基二硫代磷酸锌；
4)含硫化合物，例如二壬基萘磺酸钡、石油磺酸钙、烷硫基取代的脂肪族羧酸、脂肪族2-磺基羧酸的酯或其盐；和
5)甘油衍生物，例如甘油单油酸酯、1-(烷基苯氧基)-3-(2-羟基乙基)甘油、1-(烷基苯氧基)-3-(2,3-二羟基丙基)甘油或2-羧烷基-1,3-二烷基甘油。
适合的降凝剂选自聚甲基丙烯酸酯和烷基化萘衍生物。
适合的破乳剂选自聚醚多元醇和二壬基萘磺酸酯。
适合的摩擦改进剂选自脂肪酸和其衍生物，例如脂肪酸的天然酯(例如甘油单油酸酯)、酰胺、酰亚胺和胺(例如油胺)、含硫的二硫代氨基甲酸有机钼、含硫磷的二硫代磷酸有机钼、基于分散剂的含硫氮有机钼化合物、羧酸钼盐、钼-胺错合物、钼-胺/醇/酰胺错合物和钼簇化合物、和二硫化钼。
根据本发明的发动机油中的基础油
根据本发明的发动机油包含至少一种基础油(即具有润滑粘度的润滑剂)和根据本发明的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物，优选地其中R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物，优选地实施例12至14中所定义的添加剂掺和物。
适合的基础油为选自I至V类的矿物和合成基础油。这些基础油在美国石油学会(API)基础油互换性指南中有广泛规定。
基础油可以是油和油脂，例如基于矿物油或植物和动物油、脂肪、牛油和蜡或其混合物。植物油和动物油、脂肪、牛油和蜡例如为棕榈仁油、棕榈油、橄榄油、菜油、菜籽油、亚麻籽油、大豆油、棉絮油、葵花油、椰子油、玉米油、蓖麻油、核桃油及其混合物、鱼油，以及化学改性(例如环氧化或亚砜化)形式或通过基因工程制备的形式，例如通过基因工程制备的大豆油。
合成基础油的实例包括基于以下的润滑剂：脂肪族或芳香族羧酸酯、聚合物酯、聚环氧烷烃、磷酸酯、聚α烯烃、硅酮、烷基化苯、烷基化萘或二元酸与一元醇的二酯(例如癸二酸二辛酯或己二酸二壬酯)、三羟甲基丙烷与一元酸或与这些酸的混合物的三酯(例如三羟甲基丙烷三壬酸酯、三羟甲基丙烷三辛酸酯或其混合物)、季戊四醇与一元酸或这些酸的混合物的四酯(例如季戊四醇四辛酸酯)、或一元酸和二元酸与多元醇的复合酯(例如三羟甲基丙烷与辛酸和癸二酸的复合酯)或其混合物。除了矿物油以外，特别适合的为例如聚α烯烃、酯基润滑剂、磷酸酯、二醇、聚二醇和聚亚烷基二醇，以及它们与水的混合物。
当除了根据本发明的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物以外，优选地除了其中R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物以外还采用其它添加剂时，合乎需要(但非必需)的是制备呈上文所描述的添加剂掺和物(或添加剂包)形式的添加剂浓缩物，其包含根据本发明的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物与一种或多种所述其它添加剂的浓缩溶液或分散液，借此若干种添加剂可同时添加至基础油中以形成润滑油组合物。添加剂浓缩物至润滑油中的溶解可以通过溶剂以及通过在伴随温和加热的情况下混合来促进，但此操作并非必需。浓缩物或添加剂掺和物通常将被配制成含有适当量的添加剂，以在添加剂掺和物与预定量的基础油组合时在最终制剂中提供所需浓度。因此，根据本发明的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物可与其它所需的添加剂一起添加到少量的基础油或其它相容溶剂中，以形成添加剂掺和物，所述添加剂掺和物包含总量通常为约2.5重量％至约90重量％、优选地约15重量％至约75重量％、且更优选地约25重量％至约60重量％的活性成分(呈适当比例的添加剂)，其余为基础油。最终制剂通常可以使用约1重量％至20重量％的添加剂掺和物，其余为基础油。
根据本发明的聚合物组合物中的热塑性聚合物
除了根据本发明的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物以外，优选地除了其中R为具有式-C9H19的支链残基的结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物以外，根据本发明的聚合物组合物还包含聚合物，优选地热塑性聚合物。
使用结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的混合物，可以稳定氧化降解的热塑性聚合物包括：衍生自乙烯的包括低密度聚乙烯(LDPE)、线型低密度聚乙烯(LLDPE)、中密度聚乙烯(MDPE)、高密度聚乙烯(HDPE)的树脂，或密度为0.85至1.4gm/cm3的其它乙烯衍生树脂；衍生自C3及以上单烯和二烯不饱和烃单体的均聚物，例如聚丙烯、聚异丁烯、聚甲基丁烯-1、聚甲基戊烯-1、聚丁烯-1、聚异丁烯等；衍生自两种或更多种单体的共聚物，例如优选地至少具有大部分丙烯的乙烯-丙烯共聚物、丙烯-丁烯-1共聚物、丙烯-异丁烯共聚物等及其掺和物、聚苯乙烯；聚卤代乙烯；以及热塑性工程塑料，例如聚酰胺、聚酯、聚苯醚、聚苯硫醚、聚缩醛、脂肪族聚酮共聚物或三聚物、聚(醚砜)、聚碳酸酯、液晶聚合物、聚(醚醚酮)、聚氨酯和聚(芳基化物)。优选地，由根据本发明的组合物保护的热塑性树脂为聚氨酯或聚丙烯。
现在参考测试方法和非限制性实例来更详细地描述本发明。
发明方式
测试方法
氧化稳定性的测定
借助于加压差示扫描量热(PDSC)设备来评估氧化稳定性。
PDSC检测油在薄膜氧化条件下的氧化稳定性。在PDSC温度保持在预定值的等温模式中，根据氧化诱导时间(OIT)对测试油的氧化稳定性进行分级，对应于油的氧化开始所引起的放热。得到更长OIT的油通常被认为更耐氧化。使用以下仪器条件对各混合物进行两次测试，并测定平均OIT。PDSC测试温度为185℃。
已选择以下测量条件：
温变率：40℃/min
压力：500psi
O2流速：100ml/min
样品大小：约1.5mg
平底锅：铝，敞开
铅腐蚀的测定
根据ASTM D 6594测定铅的腐蚀。
实例
向商购的其中R表示具有式-C9H19的支链烷基的结构式(I)、(II)、(III)的烷基化二苯胺的混合物中补充不同量的结构式(IV)的对应烷基化二苯胺，之后称为“TN-DPA”(四壬基二苯胺)。已获得并分析表1中的样品：
[表1]
使用上文所描述的包含单壬基二苯胺、二壬基二苯胺、三壬基二苯胺和四壬基二苯胺的混合物的样品，制备完全完成的发动机油。为此，将样品以1.0重量％的量单独添加到不含抗氧化剂的完全完成的发动机油中。发动机油采用API第III类基础油配制而成，所述基础油由韩国首尔的SK润滑剂有限公司(SK Lubricants Co.Ltd.)提供的Yubase4和Yubase 6的混合物组成。由如此获得的润滑剂测定氧化稳定性和铅腐蚀(通过PDSC测试和ASTM D 6594测试)。PDSC测试的结果展示于表2中，且ASTM D 6594测试的结果展示于表3中：
1)两个测量值的平均值
[表3]
1)两个测量值的平均值
由表2和表3中所示的结果可以看出，将包含结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的组合物中结构式(IV)的四烷基化二苯胺的含量调整到0.2重量％至3.5重量％的极窄范围，使得组合物在添加到基础油中以用于形成发动机油时提供发动机油在氧化稳定性和针对铅腐蚀的抗性两方面的最优性能。
Claims (15)
1.一种组合物，其包含结构式(I)、(II)、(III)和(IV)的烷基化二苯胺：
其中R为支链C4-C16烷基，且
其中按所述组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计，结构式(IV)的四烷基化二苯胺的总量在0.20重量％至3.5重量％范围内。
2.根据权利要求1所述的组合物，其中按所述组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计，结构式(I)的单烷基化二苯胺的总量在10重量％至35重量％范围内。
3.根据权利要求1或2所述的组合物，其中按所述组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计，结构式(II)的二烷基化二苯胺的总量在60重量％至85重量％范围内。
4.根据权利要求1至3中任一项所述的组合物，其中按所述组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计，结构式(III)的三烷基化二苯胺的总量在1重量％至10重量％范围内。
5.根据权利要求1至4中任一项所述的组合物，其中所述组合物进一步包含按所述组合物中结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总重量计少于1重量％的非烷基化二苯胺。
6.根据权利要求1至5中任一项所述的组合物，其中残基R为具有式-C9H19的支链烷基。
7.根据权利要求1至6中任一项所述的组合物，其中满足以下条件(α1)至(α6)中的至少一个：
(α1)所述组合物的运动粘度(cinematic viscosity)(根据ASTM D 445在40℃的温度下测定)在100至1000cSt范围内；
(α2)所述组合物的加德纳色度(Gardner colour)(根据ASTM D 1544测定)小于15加德纳(Gardner)；
(α3)所述组合物的水含量(根据ASTM E 203测定)少于0.1重量％；
(α4)所述组合物的氮含量(根据ASTM D 2896测定)在3.2％至3.8％范围内；
(α5)所述组合物的比重(根据ASTM D 1298在25℃的温度下测定)在0.930至0.980范围内；
(α6)所述组合物的总碱值(TBN)(根据ASTM D 2896测定)在125至160mg KOH/g范围内。
8.根据权利要求1至7中任一项所述的组合物，其中按所述组合物的总重量计，结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量为至少98重量％。
9.根据权利要求1至6中任一项所述的组合物，其中所述组合物为添加剂掺和物。
10.根据权利要求9所述的组合物，其中按所述添加剂掺和物的总重量计，结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量在0.01重量％至30重量％范围内。
11.根据权利要求1至6中任一项所述的组合物，其中所述组合物为包含至少一种基础油的发动机油。
12.根据权利要求11所述的组合物，其中按所述发动机油的总重量计，结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量在0.01重量％至5重量％范围内。
13.根据权利要求1至6中任一项所述的组合物，其中所述组合物为包含聚合物的聚合物组合物。
14.根据权利要求13所述的组合物，其中按所述聚合物组合物的总重量计，结构式(I)、(II)、(III)和(IV)的烷基化二苯胺的总量在0.01重量％至1重量％范围内。
15.一种根据权利要求1至7中任一项所述的组合物在用作添加剂掺和物、发动机油或聚合物组合物中的添加剂的用途。
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| EP3322690B1 (en) * | 2015-07-15 | 2021-08-11 | LANXESS Corporation | Diaryl amine antioxidants prepared from branched olefins |
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