CN101389738B - 多环酚类化合物作为稳定剂的用途 - Google Patents
多环酚类化合物作为稳定剂的用途 Download PDFInfo
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- CN101389738B CN101389738B CN2007800068695A CN200780006869A CN101389738B CN 101389738 B CN101389738 B CN 101389738B CN 2007800068695 A CN2007800068695 A CN 2007800068695A CN 200780006869 A CN200780006869 A CN 200780006869A CN 101389738 B CN101389738 B CN 101389738B
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- China
- Prior art keywords
- substituent
- alkyl
- group
- carbon atom
- piperazine
- Prior art date
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- 239000003381 stabilizer Substances 0.000 title abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 103
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 77
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 65
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
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- 125000005842 heteroatom Chemical group 0.000 claims description 35
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 27
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- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical group C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims 16
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- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 6
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Classifications
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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Abstract
本发明涉及每个分子具有至多20个苯环的多环酚类化合物作为稳定剂用于稳定无生命的有机材料对抗光、氧气和热的作用的用途,所述多环酚类化合物通过将四氢苯并噁嗪I与一种或多种相同或不同的酚II和/或与一种或多种相同或不同的四氢苯并噁嗪I反应而获得,其中R1为烃基,以及R2、R3、R4和R5独立地为氢原子、羟基或烃基,R7、R8、R9和R10独立地为氢原子、羟基或烃基,前提是:所述取代基中的至少一个具有13~3000个碳原子,且其余取代基当为烃基时具有1~20个碳原子。
Description
本发明涉及特定的多环酚类化合物作为稳定剂用于稳定无生命的有机材料对抗光、氧气和热的作用的用途,尤其在汽轮机燃料(喷气式发动机燃料)和润滑剂组合物中作为稳定剂用于稳定无生命的有机材料对抗光、氧气和热的作用的用途。本发明进一步涉及一种包含这些多环酚类化合物的汽轮机燃料组合物和用于汽轮机燃料的添加剂浓缩物。本发明进一步涉及一种包含这些多环酚类化合物的润滑剂组合物。本发明进一步涉及一种制备这些多环酚类化合物的方法。由于这些多环酚类化合物中的一些是新物质,因此本发明还涉及这些新物质自身。
已知的是,无生命的有机材料,例如塑料和涂料,以及矿物油产品和燃料的机械、化学和/或美学性能受光、氧气和热的作用会损害。该损害典型地以材料的变黄、变色、龟裂形成或变脆的形式显示出来。利用其可以实现有机材料受光、氧气和热损害的改进保护的稳定剂或稳定剂组合物是已知的。
例如WO 05/073152(1)描述了2-烷基聚异丁烯基酚类和它们的曼尼希加合物作为抗氧化剂用于稳定无生命的有机材料对抗光、氧气和热的作用。其它待稳定的材料包括燃料,如汽油燃料、柴油燃料和汽轮机燃料,还有润滑剂组合物。在汽轮机燃料中,这些2-烷基聚异丁烯基酚类和它们的曼尼希加合物使得热稳定性改进,且减少了在汽轮机的燃料回路和燃烧系统中的沉积。
WO 03/106595(2)除公开了烃基-取代的琥珀酸衍生物和聚链烯基硫代膦酸酯以外,还公开了由烃基-取代的酚形成的曼尼希加合物,醛和胺作为汽轮机燃料(喷气式发动机燃料)中的添加剂用于改进热稳定性和减少沉积。
具有一个苯环的四氢苯并噁嗪已知作为燃料和润滑剂组合物的添加剂。例如,WO 01/25293(3)和WO 01/25294(4)公开了那类四氢苯并噁嗪作为清洁阀门并保持阀门清洁的汽油燃料清洁剂,所述四氢苯并噁嗪具有较长链基团如位于苯环上的聚异丁烯基作为取代基。根据(3)和(4)提到的制备方法,这些四氢苯并噁嗪以与母体酚上具有相应开链的曼尼希加合物的混合物获得,因而还用于汽油燃料中。
在Journal of Polymer Science,Part A,Polymer Chemistry,第31卷,第1941-1958页(5)中,D.Jamois,M.Tessier和E.Maréchal描述了适于在机油中作为淤泥分散剂的聚异丁烯-聚乙烯胺嵌段聚合物的制备方法。这些作者制备的化合物也包括通过-CH2-N(C12H25)-CH2-桥经由两个酚环的特定邻位连接的双环酚类化合物。
US 6 323 270 B1(6)公开了四氢苯并噁嗪的低聚物或聚合物,所述四氢苯并噁嗪可在氮原子和/或苯环上带有具有1~10个碳原子的烷基或者每种情形下具有6~20个碳原子的芳基、烷基芳基或芳基烷基作为取代基。所述四氢苯并噁嗪低聚物或聚合物的准确化学结构不明确。这些四氢苯并噁嗪低聚物或聚合物适于制备航空、陶器制品、包装材料、涂料、粘合剂和复合材料的制动衬片。
JP2003-255 487 A(7)公开了在每种情形下通过-CH2-N(C1-C25烷基)-CH2-桥或-CH2-N(苯基)-CH2-桥经由酚环的邻位连接的多环酚类化合物的聚合物。该酚环自身也可以被C1-C25烷基取代。酚环在聚合物分子中的数量指定为2~1002。C1-C25烷基提到的具体实例是甲基、乙基、丁基、辛基和十二烷基。没有提到具有低聚或聚合物分布的取代基。这些多环酚类化合物的聚合物推荐作为光热敏性成像材料。
尤其对于矿物油产品和燃料领域,需要具有改进的保护作用以对抗材料性能受光、氧和热损害的稳定剂和抗氧化剂。尤其是对于汽轮机燃料(喷气式发动机燃料),这些燃料在汽轮机、例如航空汽轮机中的燃烧操作期间和之前暴露在极度热应力下,正在寻找新的改进稳定剂。在汽轮机中,这些还应当同时借助于它们作为抗氧化剂和/或分散剂的作用模式减少在燃料回路和燃烧系统中的沉积。而且,人们正寻找润滑剂组合物的新的改进稳定剂,该稳定剂尤其提供对抗氧化和老化行为的改进保护和/或提供改进的剪切稳定性。
因此,本发明的目的是提供改进无生命的有机材料、尤其是矿物油产品和燃料(尤其是汽轮机燃料和润滑剂组合物)对光、氧气和热的作用的稳定性的稳定剂。
因此,已经发现了每个分子具有至多20个苯环的多环酚类化合物作为稳定剂用于稳定无生命的有机材料对抗光、氧气和热的作用的用途,所述多环酚类化合物可通过将通式I的四氢苯并噁嗪
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,和
其中取代基R2、R3、R4和R5彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
与一种或多种相同或不同的通式II的酚
其中取代基R7、R8、R9和R10彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
和/或与一种或多种相同或不同的通式I的四氢苯并噁嗪反应而获得,
其中取代基R4也可以是式Z基团,和取代基R9也可以是式Z’基团
其中取代基R1、R2、R3、R5、R7、R8和R10各自定义如上,取代基R7也可以为衍生自通式I的四氢苯并噁嗪的基团,取代基R15为氢或衍生自通式I的四氢苯并噁嗪的基团,以及取代基R11和R12可相同或不同且各自为氢或C1-C10烷基,
以及其中取代基R2和R3或R3和R4或R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-一起也可以形成第二个四氢噁嗪环,或取代基R2和R3及R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-和-O-CH2-NR14-CH2-一起也可以形成第二和第三个四氢噁嗪环,其中R13和R14彼此独立地为在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
前提是:取代基R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14中的至少一个具有13~3000个碳原子,且R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14这组中的其余取代基,当它们是烃基时,各自具有1~20个碳原子。
根据本发明使用的多环酚类化合物的结构特性是:它们包含至少一个具有13~3000个碳原子的较长链烃基作为源自所用四氢苯并噁嗪I或酚II的取代基R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14之一。在优选的实施方案中,该具有13~3000个碳原子的较长链烃基是聚异丁烯基。在另一个实施方案中,提到的较长链烃基也可以是C16-C20烷基或C16-C20链烯基。尤其是,优选为聚异丁烯基的该较长链烃基存在于噁嗪环上,或者存在于苯环上的相对于酚羟基的邻位或优选对位上,即,它作为取代基R1或R2或R4或R7或R9或R13或R14。优选为聚异丁烯基的该较长链烃基优选包含21~3000个或优选21~1000个、尤其26~3000个或尤其26~500个,尤其30~3000个或尤其30~250个碳原子。在聚异丁烯基的情形下,它们的数均分子量Mn为183~42000,优选500~15000,尤其700~7000,尤其900~3000,最优选900~1100。
合适的C16-C20烷基或C16-C20链烯基合适地是相应的具有16~20个碳原子的饱和或不饱和脂肪醇的基团。此处应当提到的尤其是正十六烷基(棕榈基)、正十八烷基(硬脂基)、正二十烷基、油基、亚油基和亚麻基,这些基团由于它们的天然来源,通常以工业混合物出现。
提到的具有13~3000个碳原子的较长链烃基也可以在多环酚类化合物中出现超过1次,例如两次或三次。在优选的实施方案中,具有特定数均分子量Mn为183~42000的一个或两个聚异丁烯基在分子中以取代基R1和/或R2和/或R4和/或R7和/或R9和/或R13和/或R14出现。
R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14中不是具有13~3000个碳原子的取代基或不是数均分子量Mn为183~42000的聚异丁烯基的其余取代基彼此独立地为氢原子、羟基或当它们是烃基时,通常是具有1~20个、优选1~12个、尤其1~8个碳原子的较短链烃基,最优选是线性或支化的C1-C4烷基。后者的典型实例是甲基、乙基、正丙基、异丙基、正丁基、2-丁基、仲丁基和叔丁基。此处非常特别优选的是甲基和叔丁基。
根据本发明优选使用的多环酚类化合物四氢苯并噁嗪I也是下文定义的那些,在该化合物中,源自所用四氢苯并噁嗪I或酚II的取代基R2和/或R4和/或R7和/或R9,当它们是较短链的烃基时,是线性或支化的C1-C4烷基,尤其是甲基和/或叔丁基。当然,所述取代方式仅仅对于总计具有一个或两个四氢噁嗪环体系的四氢苯并噁嗪I是有可能的。
在式Z或Z’基团中,取代基R11和R12各自优选为氢和/或线性或支化C1-C4烷基,尤其是甲基。具有其中R11=R12=甲基的Z或Z’基团的化合物I和II衍生自双酚A[2,2-双(4-羟基苯基)丙烷]。作为该制备的结果,具有Z基团的化合物I和具有相应Z’基团的化合物I也可以混合物形式存在。
取代基R1、R2、R3、R4、R5、R7、R8、R9、R10、R13和R14的具有1~3000个或13~3000个碳原子的烃基此处应当理解为是指具有任意结构的纯烃基,该烃基从定义上讲,也可以被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔。被NR6基团间隔的典型烃基衍生自3-(二甲基氨基)丙基胺。烃基尤其为烷基、链烯基、环烷基、芳基、烷基芳基、链烯基芳基或芳基烷基。
在烃基中被NR6基团间隔还指,其中NR6基团已经在末端在形式上插入到C-H键中的那些基团,即,例如具有NH2末端基团的R1、R2、R3、R4、R5、R7、R8、R9、R10、R13和R14取代基。所述烃基例如衍生自多胺,如乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺等,其中末端氮原子之一是噁嗪环上的氮原子。
术语“烷基”包括直链和支化烷基。烷基的实例除了上述已经提到的甲基、乙基、正丙基、异丙基、正丁基、2-丁基、仲丁基和叔丁基以外,还尤其是正戊基、2-戊基、2-甲基丁基、3-甲基丁基、1,2-二甲基丙基、1,1-二甲基丙基、2,2-二甲基丙基、1-乙基丙基、正己基、2-己基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,2-二甲基丁基、1,3-二甲基丁基、2,3-二甲基丁基、1,1-二甲基丁基、2,2-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基丁基、2-乙基丁基、1-乙基-2-甲基丙基、正庚基、2-庚基、3-庚基、2-乙基戊基、1-丙基丁基、正辛基、2-乙基己基、2-丙基庚基、正壬基、正癸基、正十二烷基、正十三烷基、异十三烷基、正十四烷基(肉豆蔻基)、正十六烷基(棕榈基)、正十八烷基(硬脂基)和正二十烷基。
链烯基的实例是乙烯基、1-丙烯基、2-丙烯基、油基、亚油基和亚麻基。
环烷基的实例是C5-C7环烷基,如环戊基、环己基和环庚基,其也可以被烷基,例如甲基取代。
术语“芳基”包括单环、双环、三环和更多环的芳族烃基。在被烷基和/或链烯基(例如上述提到的那些基团)取代以得到烷基芳基或链烯基芳基的情形下,这些芳基也可以带有1、2、3、4或5个,优选1、2或3个取代基。典型的实例是苯基、甲苯基、二甲苯基、基、萘基、芴基、蒽基、菲基、并四苯基(naphthacenyl)和苯乙烯基。芳基烷基的典型实例是苄基。
当具有13~3000个碳原子的较长链烃基是聚异丁烯基时,原则上它可以基于任何常用和商业上可得的聚异丁烯,其以合适的方式引入到四氢苯并噁嗪I的合成中。所述的聚异丁烯的数均分子量Mn至少为183。优选聚异丁烯的数均分子量Mn为183~42000,更优选为500~15000,尤其为700~7000,尤其为900~3000,最优选900~1100。在本发明的上下文中,术语“聚异丁烯”也包括低聚异丁烯,如二聚、三聚、四聚、五聚、六聚和七聚异丁烯。
引入到根据本发明使用的多环酚类化合物中的聚异丁烯基优选衍生自所谓的″反应性″聚异丁烯。反应性聚异丁烯与常规聚异丁烯的不同之处在于末端双键的含量,即亚乙烯基双键[-CH-C(CH3)=CH2](α-烯烃)或乙烯基双键[-CH=C(CH3)2](β-烯烃)的含量。例如,反应性聚异丁烯包含基于聚异丁烯大分子的总量为至少50mol%的末端双键。特别优选聚异丁烯基于聚异丁烯大分子的总量具有至少60mol%,尤其是至少80mol%的末端双键。而且,基本上均聚的聚异丁烯基具有均匀的聚合物结构。在本发明的上下文中,这应当理解为是指至少85%重量、优选至少90%重量、更优选至少95%重量、尤其至少99%重量的程度由具有重复单元[-CH2C(CH3)2-]的异丁烯单元形成的聚异丁烯体系。
可以是根据本发明使用的多环酚类化合物的母体分子的聚异丁烯的另一个优选特征是,它们的至少15%重量、尤其至少50%重量、尤其至少80%重量由叔丁基[-CH2C(CH3)3]封端。
而且,对于用作根据本发明使用的多环酚类化合物的起始原料的四氢苯并噁嗪I或酚II,优选作为其基础的聚异丁烯优选的多分散指数(PDI)为1.05~10,优选1.05~3.0,尤其1.05~2.0。多分散性应理解为是指重均分子量Mw与数均分子量Mn的商(PDI=Mw/Mn)。在优选的实施方案中,多环酚类化合物中的聚异丁烯基的平均多分散指数PDI是母体四氢苯并噁嗪I和/或酚II中的聚异丁烯基的平均多分散指数PDI的至多5倍,优选至多3倍,尤其至多2倍,尤其至多1.5倍。
在本发明的上下文中,优选用作四氢苯并噁嗪I或酚II基础的聚异丁烯也应理解为是指,可通过阳离子聚合获得的且包含呈共聚形式的优选至少60%重量、更优选至少80%重量、尤其至少90%重量、特别是至少95%重量的异丁烯的所有聚合物。此外,聚异丁烯可以包含呈共聚形式的其它丁烯异构体(如1-或2-丁烯),还可以包含可与异丁烯在阳离子聚合条件下共聚的不同的烯属不饱和单体。
用于制备可用作四氢苯并噁嗪I或酚II基础的聚异丁烯的合适的异丁烯给料因此是异丁烯自身和异丁烯基C4烃料流,例如C4抽余液(raffinate)、异丁烯脱氢的C4馏分、来自蒸汽裂化器的C4馏分、来自FCC裂化器的C4馏分(FCC:流体催化裂化),前提是:它们基本上已经除去了存在其中的1,3-丁二烯。特别合适的C4烃料流通常包含小于500ppm、优选小于200ppm的丁二烯。当C4馏分用作起始原料时,除了异丁烯以外的烃认为具有惰性溶剂的作用。
可与异丁烯共聚的有用的单体包括乙烯基芳族化合物,如苯乙烯和α-甲基苯乙烯;C1-C4烷基苯乙烯,如2-、3-和4-甲基苯乙烯,以及4-叔丁基苯乙烯;具有5~10个碳原子的异烯烃,如2-甲基-1-丁烯、2-甲基-1-戊烯、2-甲基-1-己烯、2-乙基-1-戊烯、2-乙基-1-己烯和2-丙基-1-庚烯。
可用作四氢苯并噁嗪I或酚II基础的典型聚异丁烯例如是BASFAktiengesellschaft的Glissopal商标系,如Glissopal 550、Glissopal 1000和Glissopal 2300,以及BASF Aktiengesellschaft的Oppanol商标系,如Oppanol B10、B12和B15。
除了聚异丁烯基以外,对于出现的较长链烃基,也可以包括衍生自C2-C12烯烃的低聚物或聚合物并具有平均13~3000个碳原子的那些。这类具有聚合物分布的通常的多分散烃基例如是衍生自乙烯、丙烯、丁烯、苯乙烯、甲基苯乙烯、1-己烯、1-辛烯、1-癸烯或1-十二碳烯的那些。它们可以是均聚或共聚基团。它们的数均分子量Mn至少为183;它们的多分散指数PDI典型地为1.05~10。在Mn为183~约500的低分子量基团的情形下,它们也可以单分散形式存在。
在优选的实施方案中,根据本发明使用的多环酚类化合物的平均分子量Mn为411~25000。例如,分子量Mn为411代表在本发明的上下文中的多环酚类化合物的最小代表,具体为双-(邻-或对-羟基苄基)十三烷基胺。特别优选Mn为523~25000或523~17000,尤其593~25000或593~10000,尤其649~25000或649~5000。
在本发明的上下文中,典型的多环酚类化合物的实例如下,其中“PIB”代表衍生自高反应性聚异丁烯(Mn 1000)的聚异丁烯基:
(IIIa)n=0,R1=PIB,R4=H
(IIIb)n=0,R1=甲基,R4=PIB
(IIIc)n=0,R1=PIB,R4=叔丁基
(IIId)n=1,R1=PIB,R4=H
(IIIe)n=1,R1=甲基,R4=PIB
(IIIf)n=1,R1=PIB,R4=叔丁基
(IIIg)n=2,R1=PIB,R4=H
(IIIh)n=2,R1=甲基,R4=PIB
(IIIi)n=2,R1=PIB,R4=叔丁基
(IIIj)n=3,R1=PIB,R4=H
(IIIk)n=3,R1=甲基,R4=PIB
(IIIl)n=3,R1=PIB,R4=叔丁基
(IIIm)n=4,R1=PIB,R4=H
(IIIn)n=4,R1=甲基,R4=PIB
(IIIo)n=4,R1=PIB,R4=叔丁基
(IIIp)n=5,R1=PIB,R4=H
(IIIq)n=5,R1=甲基,R4=PIB
(IIIr)n=5,R1=PIB,R4=叔丁基
(IIIs)n=6,R1=PIB,R4=H
(IIIt)n=6,R1=甲基,R4=PIB
(IIIu)n=6,R1=PIB,R4=叔丁基
(IIIv)n=1,R1=甲基,
1个R4基团=PIB,2个R4基团=叔丁基
(IIIw)n=8,R1=甲基,
1个R4基团=PIB,2个R4基团=叔丁基
(IVa)R1=甲基,R2=H,R4=叔丁基,R9=PIB
(IVb)R1=甲基,R2=R4=叔丁基,R9=PIB
(IVc)R1=PIB,R2=R4=叔丁基,R9=H
(IVd)R1=PIB,R2=R4=R9=H
(IVe)R1=PIB,R2=R4=H,R9=叔丁基
(IVf)R1=PIB,R2=H,R4=叔丁基,R9=PIB
(IVg)R1=PIB,R2=R4=叔丁基,R9=PIB
(Va)R1=甲基,R2=R4=H,R9=PIB
(Vb)R1=甲基,R2=R4=叔丁基,R9=PIB
(Vc)R1=甲基,R2=叔丁基,R4=甲基,R9=PIB
(Vd)R1=R2=甲基,R4=叔丁基,R9=PIB
(Ve)R1=3-(二甲基氨基)丙基,R2=R4=叔丁基,R9=PIB
(Vf)R1=PIB,R2=R4=R9=H
(Vg)R1=PIB,R2=R4=H,R9=叔丁基
(Vh)R1=PIB,R2=R4=叔丁基,R9=H
(Vi)R1=PIB,R2=H,R4=R9=叔丁基
(Vj)R1=PIB,R2=R4=R9=叔丁基
(Vk)R1=PIB,R2=R4=H,R9=PIB
(Vn)R1=3-(二甲基氨基)丙基、R2=叔丁基,R4=甲基,R9=PIB
(VIa)R1=甲基,R2=叔丁基,3个R4基团=叔丁基,1个R4基团=PIB
(VIb)R1=甲基,R2=叔丁基,3个R4基团=甲基,1个R4基团=PIB
(VIc)R1=甲基,3个R2基团=叔丁基,1R2=H,3R4=叔丁基,1个R4基团(当R2=H时,在苯环上)=PIB
所述的多环酚类化合物根据本发明用作稳定剂以稳定无生命的有机材料对抗光、氧气和热的作用。这应理解为尤其是指,它们的作用模式如常规意义的抗氧化剂那样。为此,在待稳定的材料的制备期间或之后,将这些化合物掺入到该待稳定的材料中并尽可能均匀分布。这些化合物在待稳定的有机材料中的浓度基于有机材料通常为0.0001~5%重量,优选0.001~5%重量,尤其0.01~2%重量,尤其0.05~1%重量。
无生命的有机材料应理解为是指例如:化妆品制剂,如软膏和洗剂;药品配制剂,如丸剂和栓剂;光学记录材料,尤其是感光乳剂;油漆和塑料。它们尤其进一步包括矿物油产品和燃料,例如柴油燃料、汽油燃料、汽轮机燃料、马达油或润滑油、变速箱油和润滑脂。
可通过所述多环酚类化合物稳定的塑料的实例包括:
单-或二烯烃的聚合物,如低密度或高密度聚乙烯、聚丙烯、线性聚-1-丁烯、聚异戊二烯、聚丁二烯、单-或二烯烃的共聚物或者所提到的聚合物的混合物;
聚苯乙烯和苯乙烯或α-甲基苯乙烯与二烯和/或丙烯酸衍生物的共聚物,例如苯乙烯-丁二烯、苯乙烯-丙烯腈(SAN)、苯乙烯-甲基丙烯酸乙酯、苯乙烯-丁二烯-丙烯酸乙酯、苯乙烯-丙烯腈-甲基丙烯酸酯、丙烯腈-丁二烯-苯乙烯(ABS)或甲基丙烯酸甲酯-丁二烯-苯乙烯(MBS)共聚物;含卤素聚合物,例如聚氯乙烯、聚氟乙烯、聚偏二氟乙烯和它们的共聚物;
衍生自α,β-不饱和酸和它们的衍生物的聚合物,如聚丙烯酸酯、聚甲基丙烯酸酯、聚丙烯酰胺和聚丙烯腈;
衍生自不饱和的醇和胺或衍生自它们的酰基衍生物或缩醛的聚合物,例如聚乙烯醇和聚乙酸乙烯酯;
聚氨酯,尤其热塑性聚氨酯、聚酰胺、聚脲、聚亚苯基醚、聚酯、聚碳酸酯、聚砜、聚醚砜和聚醚酮。
可用所述多环酚类化合物稳定的油漆包括涂料,如醇酸树脂涂料、分散涂料、环氧树脂涂料、聚氨酯涂料、丙烯酸系树脂涂料和硝基纤维素涂料,或清漆,如木器保护清漆。
所述多环酚类化合物适于以特别有利的方式作为汽轮机燃料(喷气式发动机燃料)中的稳定剂。这也应理解为是指,它们的作用模式如常规意义上的抗氧化剂那样。尤其是,借助于它们作为稳定剂的作用模式,它们用于改进汽轮机燃料的稳定性。而且,尤其还由于它们作为稳定剂的作用,即它们作为分散剂的性能,因此它们防止在汽轮机的燃料系统和/或燃烧系统中的沉积。汽轮机燃料尤其用于操作航空汽轮机。
本发明进一步提供一种包含汽轮机燃料(喷气式发动机燃料)和至少一种所述多环酚类化合物的汽轮机燃料组合物。
本发明的汽轮机燃料组合物包含大部分的液体汽轮机燃料,后者例如是常用于民用或军用航空的汽轮机燃料。这些例如包括标号为喷气式发动机燃料A、喷气式发动机燃料A-1、喷气式发动机燃料B、喷气式发动机燃料JP-4、JP-5、JP-7、JP-8和JP-8+100的燃料。Jet A和Jet A-1是商业上可得的基于煤油的汽轮机燃料规范。所附的标准是ASTM D 1655和DEF STAN 91-91。Jet B是基于石脑油和煤油馏分的更高级馏分燃料。JP-4与Jet B相同。JP-5、JP-7、JP-8和JP-8+100是军用汽轮机燃料,例如如由海军和空军使用。这些标准中的一些涉及已经包含其它添加剂如缓蚀剂、结冰抑制剂、静电散逸剂等的配制剂。
所述的多环酚类化合物可单一地、作为混合物和如果合适的话,与其它本身已知的添加剂组合地加入到汽轮机燃料或者汽轮机燃料组合物中。
可存在于本发明汽轮机燃料组合物中的合适的添加剂典型地包含清洁剂、缓蚀剂、其它抗氧化剂如位阻叔丁基酚类、N-丁基苯二胺或N,N’-二苯基胺及其衍生物、金属减活剂如N,N’-二亚水杨基-1,2-二胺基丙烷、增溶剂、抗静电剂如Stadis 450、抗微生物剂、防冻剂如二甘醇甲基醚以及所提到的这些添加剂的混合物。
在本发明上下文中,优选的添加剂是下述的(A)、(B)和(C)类化合物:
优选的添加剂(A)是衍生自琥珀酸酐且通常具有带有15~700个、尤其30~200个碳原子的长链烃基的化合物。这些化合物可进一步具有优选选自下述的官能团:羟基、氨基、酰胺基和/或酰亚胺基。优选的添加剂是聚链烯基琥珀酸酐的相应衍生物,该衍生物例如可通过将聚烯烃与马来酸酐通过加热路线或经由氯代烃反应而获得。长链烃基的数均分子量优选为约200~10000、更优选400~5000、尤其600~3000、尤其650~2000。这些长链烃基优选衍生自常规聚异丁烯,尤其是前述的反应性聚异丁烯。作为添加剂(A)尤其令人感兴趣的是聚链烯基琥珀酸酐与氨、一元胺、多胺、一元醇和多元醇的衍生物。优选用于衍生的多胺包括乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、丙二胺等。合适的醇包括一元醇,如乙醇、烯丙基醇、十二烷醇和苄醇;多元醇如乙二醇、二甘醇、丙二醇、1,2-丁二醇、新戊二醇、甘油、三羟甲基丙烷、赤藓醇、季戊四醇、甘露糖醇和山梨糖醇。
适于用作添加剂的琥珀酸酐衍生物(A)例如描述在US 3 522 179、US 4234 435、US 4 849 572、US 4 904 401、US 5 569 644和US 6 165 235中,这些文献全部引入本文作为参考。
优选的添加剂(B)是聚链烯基硫代膦酸酯。这些酯的聚链烯基的数均分子量优选为约300~5000,更优选400~2000,尤其500~1500。该聚链烯基优选衍生自已经对组分(A)作为长链烃基描述的聚烯烃。它们尤其是衍生自常规的或反应性的聚异丁烯的聚链烯基。通过将聚烯烃与硫代磷酰化剂反应制备合适的聚链烯基硫代膦酸酯的合适方法描述在例如US 5 725 611中,该文献引入本文作为参考。
优选的添加剂(C)是曼尼希加合物。所述加合物原则上通过芳族羟基化合物(尤其是苯酚和苯酚衍生物)与醛和单-或多胺的曼尼希反应获得。它们优选是聚异丁烯取代的酚与甲醛和单-或多胺(如乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、二甲基氨基丙基胺等)的反应产物。合适的曼尼希加合物和它们的制备方法例如描述在US 5 876 468、EP-A 831 141、EP-A 1 233 990和EP-A 1 226 188中,这些文献全部引入本文作为参考。
本发明的汽轮机燃料组合物包含所述的多环酚类化合物,其包含量基于汽轮机燃料组合物的总量为0.0001~1%重量,优选0.001~0.5%重量、尤其0.01~0.2%重量,尤其0.01~0.1%重量。
添加剂(A)~(C)和如果合适的话,来自上文所述那些的其它添加剂典型地各自的使用量在每种情形下基于汽轮机燃料组合物的总量,可为0.0001~1%重量,优选0.001~0.6%重量,尤其0.0015~0.4%重量。
本发明进一步提供用于汽轮机燃料(喷气式发动机燃料)的添加剂浓缩物,其包含至少一种所述的多环酚类化合物和如果合适的话,至少一种稀释剂和如果合适的话,至少一种优选选自如上所述的那些的其它添加剂。在优选实施方案中,本发明的添加剂浓缩物并因而还有本发明的汽轮机燃料组合物,包含来自由(A)、(B)和(C)组成的一组中的一种或多种添加剂,尤其包含它们的混合物,如(A)+(B)、(A)+(C)、(B)+(C)和(A)+(B)+(C)。
所述的多环酚类化合物在本发明的添加剂浓缩物中的存在量基于该浓缩物的总重量优选为0.1~100%重量,更优选1~80%重量,尤其为10~70%重量。
所述的多环酚类化合物还有利地适于在汽油燃料和中间馏出的燃料中用作稳定剂,在本文中尤其是在柴油燃料和加热油中用作稳定剂。这也应当理解为包括它们的作用模式如常规意义的抗氧化剂那样。尤其是,由于它们作为稳定剂的作用模式,它们用于改进汽油燃料和中间馏出的燃料的热稳定性。尤其是,由于它们作为稳定剂的作用模式,即它们作为分散剂的性能,它们也用于防止在汽油或柴油发动机的燃料系统和/或燃烧系统中的沉积。
可能的汽油燃料包括所有商业汽油燃料组合物。此处应当提到的典型代表是根据EN 228的市场上常见的Eurosuper基础燃料。根据WO 00/47698说明书的汽油燃料组合物也是本发明的可能应用领域。
可能的中间馏出的燃料包括所有商业柴油燃料和加热油组合物。柴油燃料典型地是沸程通常为100℃~400℃的矿物油抽余液。这些通常是95%点最高360℃或甚至更高的馏出液。它们也可以是所谓的“超低硫柴油”或“城市柴油”,其特征在于95%点例如不超过345℃且硫含量不超过0.005%重量,或95%点例如不超过285℃且硫含量不超过0.001%重量。除了可通过精炼获得的其主要组分为较长链链烷烃的柴油燃料外,合适的柴油燃料还有可通过煤气化或者气体液化[“气转液”(GTL)燃料]获得的那些。合适的还有上述柴油燃料与可再生燃料(如生物柴油或生物乙醇)的混合物。现在,具有低硫含量的柴油燃料尤其令人感兴趣,即硫含量小于0.05%重量,优选小于0.02%重量,尤其小于0.005%重量,尤其小于0.001%重量的柴油燃料尤其令人感兴趣。柴油燃料也可以包含水,例如含水量至多为20%重量,例如呈柴油-水微乳液形式或作为所谓的“白色柴油”。
加热油例如是典型地沸程为150~400℃的低硫或富硫的矿物油抽余液,或烟煤馏出液或褐煤馏出液。加热油也可以是根据DIN 51603-1的标准加热油,其硫含量为0.005~0.2%重量,或硫含量为0~0.005%重量的低硫加热油。加热油的实例尤其包括用于家用烧油煮器的加热油或EL加热油。
所述的多环酚类化合物可单独或呈燃料添加剂包装体(例如所谓的柴油机性能包装体(diesel performance package))的形式加入到特定的基础燃料(尤其是汽油燃料)中或者加入到柴油燃料中。所述包装体是燃料添加剂浓缩物,除了溶剂以外通常包含一系列其它组分作为助添加剂,例如载体油、冷流改进剂、缓蚀剂、破乳剂、去雾剂、防沫剂、其它的十六烷值改进剂、其它的助燃剂、抗氧化剂或稳定剂、抗静电剂、金属茂、金属减活剂、增溶剂、标记剂和/或染料。
在优选的实施方案中,添加了添加剂的汽油燃料或柴油燃料,除了所述的多环酚类化合物以外,还包含作为其它燃料添加剂的尤其至少一种下文称作组分(D)的清洁剂。
清洁剂或清洁剂添加剂典型地是指燃料的沉积抑制剂。清洁剂优选是具有至少一个数均分子量(Mn)为85~20000、尤其300~5000、尤其500~2500的疏水烃基和至少一个选自如下的极性基团的两亲性物质:
(Da)单氨基或具有至多6个氮原子的多氨基基团,其中至少一个氮原子呈碱性;
(Db)硝基,如果合适的话与羟基组合;
(Dc)与单-或多氨基基团组合的羟基,其中至少一个氮原子呈碱性;
(Dd)羧基或它们的碱金属或碱土金属盐;
(De)磺酸基或它们的碱金属或碱土金属盐;
(Df)被羟基封端的聚氧化-C2-C4-亚烷基基团,被单-或多氨基基团封端的聚氧化-C2-C4-亚烷基基团,其中至少一个氮原子呈碱性,或被氨基甲酸酯基封端的聚氧化-C2-C4-亚烷基基团;
(Dg)羧酸酯基团;
(Dh)衍生自琥珀酸酐且带有羟基和/或氨基和/或酰胺基和/或酰亚胺基的基团;和/或
(Di)通过取代的酚与醛类和单-或多胺类的曼尼希反应获得的基团。
上述清洁剂添加剂中的疏水烃基能够确保在燃料油组合物中具有足够的溶解度,该疏水烃基的数均分子量(Mn)为85~20000,尤其为300~5000,尤其为500~2500。典型的疏水烃基(尤其是与极性基团(Da)、(Dc)、(Dh)和(Di)组合)包括较长链的烷基或链烯基,尤其是聚丙烯基、聚丁烯基和聚异丁烯基,这些基团各自具有的Mn=300~5000,尤其500~2500、尤其700~2300。
上述清洁剂添加剂的实例包括下述:
包含单-或多氨基基团(Da)的添加剂优选为基于Mn=300~5000的聚丙烯或常规(即主要带有内双键)聚丁烯或聚异丁烯的聚烯烃单胺或聚烯烃多胺。当主要带有内双键(通常在β-和γ-位)的聚丁烯或聚异丁烯在制备添加剂中用作起始原料时,可能的制备路线如下:通过氯化作用和随后的胺化作用或者通过双键与空气或臭氧的氧化作用以获得羰基或羧基化合物,随后在还原性(氢化)条件下进行胺化作用。此处用于胺化作用的胺类可以是例如氨、单胺或多胺,如二甲基氨基丙基胺、乙二胺、二亚乙基三胺、三亚乙基四胺或四亚乙基五胺。基于聚丙烯的相应添加剂尤其描述在WO-A-94/24231中。
包含单氨基基团(Da)的其它优选添加剂为平均聚合度P=5~100的聚异丁烯与氮氧化物或者与氮氧化物与氧气的混合物的反应产物的氢化产物,这些尤其描述在WO-A-97/03946中。
包含单氨基基团(Da)的其它优选添加剂为可通过聚异丁烯环氧化物与胺反应、随后脱水以及还原氨基醇获得的化合物,这些尤其描述在DE-A-196 20 262中。
包含硝基(如果合适的话,与羟基组合)(Db)的添加剂优选为平均聚合度P=5~100或10~100的聚异丁烯与氮氧化物或者与氮氧化物与氧气的混合物的反应产物,这些尤其描述在WO-A-96/03367和WO-A-96/03479中。这些反应产物通常是纯的硝基聚异丁烯(如α,β-二硝基聚异丁烯)与混合的羟基硝基聚异丁烯(如α-硝基-β-羟基聚异丁烯)的混合物。
包含与单-或多氨基基团组合的羟基(Dc)的添加剂尤其是可通过优选主要带有末端双键且Mn=300~5000的聚异丁烯获得的聚异丁烯环氧化物与氨或单-或多胺的反应产物,这些尤其描述在EP-A-476 485中。
包含羰基或它们的碱金属或碱土金属盐(Dd)的添加剂优选是C2-C40-烯烃与马来酸酐的共聚物,该共聚物的总摩尔质量为500~20000且其一些或全部羧基已经转化成碱金属或碱土金属盐,而其余羧基已经与醇或胺反应。所述添加剂尤其公开在EP-A-307 815中。所述添加剂主要用于防止阀座磨损,且如WO-A-87/01126所述,可有利地与常规燃料清洁剂,如聚(异)丁烯胺或聚醚胺结合使用。
包含磺酸基团或它们的碱金属或碱土金属盐(De)的添加剂优选是磺基琥珀酸烷基酯的碱金属或碱土金属盐,这些尤其描述在EP-A-639 632中。所述的添加剂主要用于防止阀座磨损,且可有利地与常规燃料清洁剂,如聚(异)丁烯胺或聚醚胺结合使用。
包含聚氧化-C2-C4-亚烷基基团(Df)的添加剂优选为可通过如下方式获得的聚醚或聚醚胺:使C2-C60链烷醇、C6-C30链烷二醇、单-或二-C2-C30烷基胺、C1-C30烷基环己醇或C1-C30烷基酚与以每羟基或氨基计为1~30mol的环氧乙烷和/或环氧丙烷和/或环氧丁烷进行反应,在聚醚胺的情形下,随后用氨、单胺或多胺进行还原胺化。所述产物尤其描述在EP-A-310 875、EP-A-356 725、EP-A-700 985和US-A-4 877 416中。在聚醚的情形下,所述产物也可以具有载体油的性能。这些的典型实例是十三烷醇、异十三烷醇、异壬基酚和聚异丁烯醇的丁氧化物和丙氧化物,以及相应的与氨的反应产物。
包含羧酸酯基团(Dg)的添加剂优选是单-、二-或三羧酸与长链的链烷醇或多元醇形成的酯,尤其是在100℃下最小粘度为2mm2/s的那些酯,这些尤其描述在DE-A-38 38 918中。所用的单-、二-或三羧酸可以是脂族或芳族酸,尤其适宜的酯醇或酯多元醇是例如具有6~24个碳原子的长链醇。典型的酯代表是异辛醇、异壬醇、异癸醇和异十三烷醇的己二酸酯、邻苯二甲酸酯、间苯二甲酸酯、对苯二甲酸酯和偏苯三甲酸酯。所述产物也具有载体油的性能。
包含衍生自琥珀酸酐且带有羟基和/或氨基和/或酰胺基和/或酰亚胺基(Dh)的添加剂优选是烷基-或链烯基-取代的琥珀酸酐的相应衍生物,尤其是聚异丁烯基琥珀酸酐的衍生物,该聚异丁烯基琥珀酸酐的衍生物可通过使Mn=300~5000的常规的或高反应性的聚异丁烯与马来酸酐通过热路线或经由氯化聚异丁烯进行反应而获得。特别感兴趣的是与脂族多胺如乙二胺、二亚乙基三胺、三亚乙基四胺或四亚乙基五胺形成的衍生物。带有羟基和/或氨基和/或酰胺基和/或酰亚胺基的基团是例如:羧酸基团,单胺的酰胺,除了酰胺官能团以外还带有游离胺基团的二或多胺的酰胺,带有酸和酰胺官能团的琥珀酸衍生物,与单胺的羧酰亚胺,除了酰亚胺官能团以外还带有游离胺基团的与二-或多胺的羧酰亚胺,或通过二-或多胺与两种琥珀酸衍生物反应形成的二酰亚胺。所述燃料添加剂尤其描述在US-A-4 849 572中。
基团(Dh)的清洁剂添加剂优选是烷基-或链烯基-取代的琥珀酸酐(尤其是聚异丁烯基琥珀酸酐)与胺和/或醇的反应产物。因而它们是衍生自烷基-、链烯基-或聚异丁烯基琥珀酸酐且带有氨基和/或酰胺基和/或酰亚胺基和/或羟基的衍生物。应当理解的是,这些反应产物不仅当使用取代的琥珀酸酐时可获得,而且当使用取代的琥珀酸或合适的酸衍生物如琥珀酰卤或琥珀酸酯时也可获得。
在优选的实施方案中,添加了添加剂的燃料包含至少一种基于聚异丁烯基-取代的琥珀酰亚胺的清洁剂。特别感兴趣的是与脂族多胺的酰亚胺。特别优选的多胺是乙二胺、二亚乙基三胺、三亚乙基四胺、五乙基六胺、尤其是四亚乙基五胺。聚异丁烯基的数均分子量Mn优选为500~5000,更优选500~2000,尤其约1000。
包含通过取代的酚与醛类和单-或多胺的曼尼希反应获得的基团(Di)的添加剂优选是聚异丁烯-取代的酚与甲醛和单-或多胺如乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺或二甲基氨基丙基胺的反应产物。聚异丁烯基取代的酚可源自Mn=300~5000的常规的或高反应性的聚异丁烯。所述“聚异丁烯-曼尼希碱”尤其描述在EP-A-831 141中。
与所述的多环酚类化合物一起提到的清洁剂添加剂(D)优选与至少一种载体油组合使用。
合适的矿物载体油是在原油加工过程中获得的粘度例如为SN 500-2000等级的馏分,如光亮油或基础油;以及芳族烃,石蜡烃和烷氧基链烷醇。同样有用的是在矿物油精炼中获得的且已知为“加氢裂化油”(沸程为约360~500℃的真空馏出液,其可由天然矿物油经在高压下催化加氢和异构化以及脱蜡获得)的馏分。同样合适的是上述矿物载体油的混合物。
合适的合成载体油的实例选自:聚烯烃(聚-α-烯烃或聚(内烯烃))、(聚)酯、(聚)烷氧基化物、聚醚、脂族聚醚胺、烷基酚起始的聚醚、烷基酚起始的聚醚胺和长链链烷醇的羧酸酯。
合适聚烯烃的实例是Mn=400~1800的烯烃聚合物,尤其是基于聚丁烯或聚异丁烯(氢化或未氢化)的聚合物。
合适的聚醚或聚醚胺的实例优选是包含聚氧化-C2-C4-亚烷基基团的化合物,该化合物可通过如下反应获得:使C2-C60链烷醇、C6-C30链烷二醇、单-或二-C2-C30烷基胺、C1-C30烷基环己醇或C1-C30烷基酚与以每羟基或氨基计为1~30mol的环氧乙烷和/或环氧丙烷和/或环氧丁烷进行反应,在聚醚胺的情形下,随后用氨、单胺或多胺进行还原胺化。所述产物尤其描述在EP-A-310 875、EP-A-356 725、EP-A-700 985和US-A-4 877 416中。例如所用的聚醚胺可以为聚-C2-C6-氧化亚烷基胺或其官能化衍生物。它们的典型实例是十三烷醇、异十三烷醇、异壬基酚和聚异丁烯醇的丁氧化物和丙氧化物,以及相应的与氨的反应产物。
长链的链烷醇的羧酸酯的实例尤其是单-、二-或三羧酸与长链的链烷醇或多元醇形成的酯,这些尤其描述在DE-A-38 38 918中。所用的单-、二-或三羧酸可以是脂族或芳族酸;合适的酯醇或多元醇尤其是具有例如6~24个碳原子的长链醇。典型的酯代表是异辛醇、异壬醇、异癸醇和异十三烷醇的己二酸酯、邻苯二甲酸酯、间苯二甲酸酯、对苯二甲酸酯和偏苯三甲酸酯,例如邻苯二甲酸二-(正或异十三烷基)酯。
其它合适的载体油体系例如描述在DE-A-38 26 608、DE-A-41 42 241、DE-A-43 09 074、EP-A-0 452 328和EP-A-0 548 617中。
特别合适的合成载体油的实例是醇起始的聚醚,该聚醚具有约5~35个,例如约5~30个C3-C6氧化烯单元,后者例如选自氧化丙烯、氧化正丁烯和氧化异丁烯单元或其混合物。合适的起始剂醇的非限制性实例是长链的链烷醇或被长链烷基取代的酚,在该取代酚中,所述长链烷基尤其是直链或支化C6-C18烷基。优选的实例包括十三烷醇和壬基酚。
其它合适的合成载体油是烷氧基化的烷基酚,这些描述在DE-A-10 102913中。
优选的载体油是合成载体油,特别优选聚醚。
将清洁剂添加剂(D)或该类型的不同清洁剂添加剂的混合物加入到添加了添加剂的燃料中,其添加的总量优选为10~2000ppm重量,更优选20~1000ppm重量,甚至更优选50~500ppm重量,尤其50~200ppm重量,例如70~150ppm重量。
当额外使用载体油时,将它加入到本发明的添加了添加剂的燃料中,其添加量优选为1~1000ppm重量,更优选10~500ppm重量,尤其20~100ppm重量。
适于用作其它助添加剂的冷流变改进剂例如是乙烯与至少一种其它的不饱和单体的共聚物,例如乙烯-乙酸乙烯酯共聚物。
适于用作其它助添加剂的缓蚀剂例如是琥珀酸酯,尤其是与多元醇的琥珀酸酯,脂肪酸衍生物,例如油酸酯,低聚脂肪酸和取代的乙醇胺。
适于用作其它助添加剂的破乳剂例如是碱金属和碱土金属的烷基取代的苯酚磺酸盐和萘磺酸盐,脂肪酸的碱金属和碱土金属盐,以及醇烷氧化物(如醇乙氧化物),酚烷氧化物(如叔丁基酚乙氧化物或叔戊基酚乙氧化物),脂肪酸,烷基酚,环氧乙烷和环氧丙烷的缩合产物(如氧化乙烯-氧化丙烯的嵌段共聚物),聚乙烯亚胺和聚硅氧烷。
适于用作其它助添加剂的去雾剂例如是烷氧基化的酚-甲醛缩合物。
适于用作其它助添加剂的防沫剂例如是聚醚改性的聚硅氧烷。
适于用作其它助添加剂的十六烷值改进剂和助燃剂例如是硝酸烷基酯,如硝酸环己基酯,尤其是硝酸2-乙基己基酯,过氧化物,如过氧化二-叔丁基。
适于用作其它助添加剂的抗氧化剂例如是取代的苯酚,如2,6-二-叔丁基酚和2,6-二-叔丁基-3-甲基酚,和苯二胺,如N,N’-二-仲丁基对苯二胺。
适于用作其它助添加剂的金属减活剂例如是水杨酸衍生物,如N,N’-二亚水杨基-1,2-丙烷二胺。
合适的溶剂,尤其是用于燃料添加剂包装体的合适的溶剂,例如是非极性有机溶剂,尤其是芳族和脂族烃,例如甲苯、二甲苯、“石油溶剂”和名称为Shellsol(制造商:Royal Dutch/Shell Group)、Exxol(制造商:ExxonMobil)和溶剂石脑油的工业溶剂混合物。此处有用的溶剂,尤其是在与提到的非极性有机溶剂的共混物中的有用溶剂,是极性有机溶剂,尤其是醇如2-乙基己醇、癸醇和异十三烷醇。
当提到的助添加剂和/或溶剂也用于汽油燃料或柴油燃料中时,它们以常规量使用。
所述的多环酚类化合物也特别有利地适于在润滑剂中作为稳定剂。润滑剂或润滑剂组合物此处应当理解为马达油、润滑油、包括手动和自动油在内的润滑油以及用于机械润滑移动部件-通常作为金属-相关的流体组合物。此处,稳定化应理解为尤其是指,润滑剂组合物的氧化和老化稳定性的改进,即它们尤其作为抗氧化剂的作用。此外或者可选择地,所述多环酚类化合物改进润滑剂组合物的剪切稳定性,即多环酚类化合物更有效地增稠润滑剂组合物。在某些情形下,所述的多环酚类化合物在润滑剂组合物中还起分散剂的作用。
本发明进一步提供一种润滑剂组合物,其包含对此常规的组分和至少一种所述的多环酚类化合物。本发明的润滑剂组合物包含的所述多环酚类化合物的量基于该润滑剂组合物的总量典型地为0.001~20%重量,优选0.01~10%重量,尤其0.05~8%重量,尤其0.1~5%重量。
经济上最重要的润滑剂组合物是马达油,以及包括手动和自动油在内的润滑油。马达油典型地包含主要包含石蜡组分且在精炼中通过昂贵的不便利的处理和纯化工艺生产的矿物基础油,该马达油的添加剂的分数为大约2~10%重量(基于活性物质内容物)。对于具体应用,例如高压应用,矿物基础油可部分或全部被如下组分代替:合成组分如有机酯,合成烃如烯烃低聚物,氢化裂化油的聚-α-烯烃或聚烯烃。马达油在高温下还必须具有足够高的粘度以确保在汽缸和活塞之间无缺陷的润滑效果和良好的密封。而且,马达油的流动性能必须使得发动机可以在低温下毫无困难地启动。马达油必须是氧化稳定的,且必须甚至在困难的工作条件下仅产生少量的呈液态或固态形式的分解产物和沉积物。马达油会分散固体(分散剂行为)、防止沉积(清洁剂行为)、中和酸性反应产物并在发动机的金属表面上形成保护膜。马达油典型的特征在于粘度级别(SAE级别)。
关于它们的基本组分和添加剂,包括手动和自动油在内的润滑油具有与马达油相似的组成。在变速箱的齿轮系统中,应力高度地通过在齿轮间的润滑油中的液压传递。因此润滑油必须使得它能长期承受高压而不会分解。这里,除粘度性能以外,磨损、耐压性、摩擦、剪切稳定性、牵引和运行性能是重要参数。
在本发明的上下文中,除了待使用的多环酚类化合物,马达油和包括手动和自动油在内的润滑油通常也包含对于它们而言为常规量的下面列出的添加剂中的至少一种,但经常是一部分或全部(括号中以%重量示出,基于整个润滑剂组合物):
(a)抗氧化剂(0.1~5%):
硫化合物,例如萜烯(α-蒎烯)、树脂油或低分子量的聚丁烯与硫、二烷基硫、二烷基三硫化物、多硫化物、二芳基硫、改性硫醇、巯基苯并咪唑、巯基三嗪、噻吩衍生物、黄原酸酯、二烷基二硫代氨基甲酸锌、硫基乙醇、硫醛、二苄二硫、烷基酚硫化物、二烷基酚硫化物或含硫羧酸的反应产物
磷化合物,例如亚磷酸三芳基酯和亚磷酸三烷基酯、3,5-二-叔丁基-4-羟基苄基膦酸二烷基酯或膦酸哌嗪化物(piperazide)
硫-磷化合物,例如二烷基二硫代磷酸锌(二烷基二硫代磷酸金属盐也作为润滑油中的缓蚀剂和高压添加剂),或五硫化磷与萜烯(α-蒎烯、二聚戊烯)、聚丁烯、烯烃或不饱和酯的反应产物
酚衍生物,例如位阻单-、双-或三酚,位阻多环酚,聚烷基酚,2,6-二-叔丁基-4-甲基酚或亚甲基-4,4’-双(2,6-二-叔丁基酚)(酚衍生物经常与硫基或胺基抗氧化剂组合使用)
胺类,例如芳基胺,如二苯基胺、苯基-α-萘基胺或4,4’-四甲基二氨基二苯基甲烷
较狭义意义上的金属减活剂,例如N-亚水杨基乙基胺、N,N’-二亚水杨基乙二胺、N,N’-二亚水杨基-1,2-丙烷二胺、三亚乙基二胺、乙二胺四乙酸、磷酸、柠檬酸、羟基乙酸、卵磷脂、噻二唑、咪唑或吡唑衍生物
(b)粘度指数改进剂(0.05~10%),例如:分子量典型地为10000~45000的聚异丁烯、分子量典型地为15000~100000的聚甲基丙烯酸酯、分子量典型地为80000~100000的1,3-二烯(如丁二烯或异戊二烯)的均聚物和共聚物、分子量典型地为80000~100000的1,3-二烯-苯乙烯共聚物、分子量典型地为60000~120000的呈酯化形式的马来酸酐-苯乙烯聚合物、分子量典型地为200000~500000的借助于由共轭二烯和芳族单体构成的单元的嵌段样结构的星形聚合物、分子量典型地为80000~150000的聚烷基苯乙烯、分子量典型地为60000~140000的由乙烯和丙烯构成的聚烯烃或者苯乙烯-环戊二烯-降冰片烯的三元聚合物
(c)倾点下降剂(冷流改进剂)(0.03~1%),例如双环芳族化合物,如具有不同的长链烷基的萘,在醇基团中具有12~18个碳原子、支化度为10~30mol%且平均分子量为5000~500000的聚甲基丙烯酸酯,长链烷基酚和二烷基芳基邻苯二甲酸酯或不同烯烃的共聚物
(d)清洁剂(HD添加剂)(0.2~4%),例如环烷酸钙、环烷酸铅、环烷酸锌和环烷酸锰,二氯硬脂酸钙、苯基硬脂酸钙、氯苯基硬脂酸钙,烷基芳族化合物(如十二烷基苯)的磺化产物,石油磺酸酯、磺酸钠、磺酸钙、磺酸钡或磺酸镁,中性、碱性和过碱性的磺酸盐、酚盐和羧酸盐,水杨酸盐,烷基酚和烷基酚硫化物的金属盐,磷酸酯、硫代磷酸酯或链烯基膦酸衍生物
(e)无灰分散剂(0.5~10%),例如烷基酚、甲醛和聚亚烷基多胺的曼尼希缩合物,聚异丁烯基琥珀酸酐与多羟基化合物或多胺的反应产物,甲基丙烯酸烷基酯与甲基丙烯酸二乙基氨基乙基酯、N-乙烯基吡咯烷酮、N-乙烯基吡啶或甲基丙烯酸2-羟基乙基酯的共聚物,或乙酸乙烯酯-富马酸乙烯酯共聚物
(f)高压添加剂(特压添加剂)(0.2~2.5%),例如氯含量为40~70%重量的氯化石蜡、氯代脂肪酸(尤其是具有三氯甲基的末端基团)、二烷基亚磷酸氢酯、三芳基亚磷酸酯、芳基磷酸酯(如三甲酚磷酸酯)、二烷基磷酸酯、三烷基磷酸酯(如三丁基磷酸酯)、三烷基膦、二磷酸酯、硝基芳族化合物、环烷酸的氨基酚衍生物、氨基甲酸酯、二硫代氨基甲酸衍生物、取代的1,2,3-三唑、苯并三唑和烷基琥珀酸酐或烷基马来酸酐的混合物、1,2,4-噻二唑聚合物、吗啉并苯并噻二唑二硫化物、氯代烷基硫化物、硫化烯烃、硫化氯萘、氯代烷基硫代碳酸酯、有机硫化物和多硫化物,如双(4-氯苄基)二硫化物和四氯二苯基硫、三氯丙烯醛缩硫醛或尤其二烷基二硫代磷酸锌(ZDDP)
(g)摩擦改进剂(0.05~1%),尤其是在摩擦表面通过吸附产生薄层的极性的油溶性化合物,例如脂肪醇、脂肪酰胺、脂肪酸盐、脂肪酸烷基酯或脂肪酸甘油酯
(h)防沫剂添加剂(0.0001~0.2%),例如液体聚硅氧烷,如聚二甲基硅氧烷或聚乙二醇醚和硫化物
(i)破乳剂(0.1~1%),例如呈其碱金属和碱土金属盐形式的二壬基萘磺酸盐
(j)缓蚀剂(已知也为金属减活剂)(0.01~2%),例如叔胺及其盐,亚胺酯,酰胺肟,二氨基甲烷,饱和或不饱和脂肪酸与烷醇胺的衍生物,烷基胺,肌氨酸,咪唑啉,烷基苯并三唑,二巯基噻二唑衍生物,二芳基磷酸酯,硫代磷酸酯,伯正C8-C18烷基胺或环烷基胺与带有支化C5-C12烷基的二烷基磷酸酯的中性盐,中性或碱性碱土金属磺酸盐,环烷酸锌,单-和二烷基芳基磺酸盐,二壬基萘磺酸钡,羊毛脂(羊毛脂),环烷酸、二羧酸、不饱和脂肪酸、羟基脂肪酸、脂肪酸酯、季戊四醇单油酸酯和脱水山梨糖醇单油酸酯的重金属盐,O-硬脂酰基烷醇胺,聚异丁烯基琥珀酸衍生物,或二烷基二硫代磷酸锌和二烷基二硫代氨基甲酸锌
(k)乳化剂(0.01~1%),例如长链不饱和的天然存在的羧酸,环烷酸,合成羧酸,磺酰胺,N-油基肌氨酸,烷基磺酰胺乙酸,十二烷基苯磺酸盐,长链烷基化铵盐如二甲基十二烷基苄基氯化铵,咪唑啉鎓盐,烷基-、烷基芳基-、酰基-、烷基氨基-和酰基氨基聚乙二醇,或长链的酰化的单-和二乙醇胺
(l)染料和荧光添加剂(0.001~0.2%)
(m)防腐剂(0.001~0.5%)
(n)气味改进剂(0.001~0.2%)。
在本发明的上下文中,典型的即用型马达油配制剂和包括手动和自动油在内的润滑油配制剂具有下述组成,其中各添加剂的数据指活性物质含量并且所有组分的总和总是为100%重量:
·80~99.3%重量、尤其90~98%重量的马达基础油或包括手动和自动油在内的润滑基础油(矿物基础油和/或合成组分),这些基础油包括用于添加剂的溶剂和稀释剂部分
·0.1~8%重量作为稳定剂的多环酚化合物
·0.2~4%重量、尤其1.3~2.5%重量的(d)组的清洁剂
·0.5~10%重量、尤其1.3~6.5%重量的(e)组的分散剂
·0.1~5%重量、尤其0.4~2.0%重量的(a)组的抗氧化剂和/或(f)组的高压添加剂和/或(g)组的摩擦改进剂
·0.05~10%重量、尤其0.2~1.0%重量的(b)组的粘度指数改进剂
·0~2%重量的(c)和(h)~(n)组的其它添加剂。
本发明还提供一种制备所述多环酚类化合物的方法,其包括将四氢苯并噁嗪I与一种或多种相同或不同的酚II和/或与一种或多种相同或不同的四氢苯并噁嗪I在60~250℃、尤其90~150℃的温度下,在无惰性溶剂存在下或在惰性溶剂(例如芳族烃,如甲苯或二甲苯)的存在下进行反应。
由于某些所述的多环酚类化合物是新物质,因此这些新物质本身也构成本发明主题的一部分。
带有至少一个具有至少26个碳原子的较长链烃基的多环酚类化合物是新的。因此本发明还提供每个分子具有至多20个苯环且可通过下述方式获得的多环酚类化合物:
将通式I的四氢苯并噁嗪
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,和
其中取代基R2、R3、R4和R5彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
与一种或多种相同或不同的通式II的酚
其中取代基R7、R8、R9和R10彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
和/或与一种或多种相同或不同的通式I的四氢苯并噁嗪反应,
其中取代基R4也可以是式Z基团,和取代基R9也可以是式Z’基团
其中取代基R1、R2、R3、R5、R7、R8和R10各自定义如上,取代基R7也可以为衍生自通式I的四氢苯并噁嗪的基团,取代基R15为氢或衍生自通式I的四氢苯并噁嗪的基团,以及取代基R11和R12可相同或不同且各自为氢或C1-C10烷基,
以及其中取代基R2和R3或R3和R4或R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-一起也可以形成第二个四氢噁嗪环,或取代基R2和R3及R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-和-O-CH2-NR14-CH2-一起也可以形成第二和第三个四氢噁嗪环,其中R13和R14彼此独立地为在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
前提是:取代基R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14中的至少一个具有26~3000个碳原子,且R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14这组中的其余取代基,当它们是烃基时,各自具有1~20个碳原子。
带有至少一个具有平均至少13个碳原子的较长链烃基的多环酚类化合物是新的,其中所述的较长链烃基衍生自C2-C12烯烃的低聚物或聚合物。因此本发明还提供每个分子具有至多20个苯环且可通过下述方式获得的多环酚类化合物:
将通式I的四氢苯并噁嗪
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,和
其中取代基R2、R3、R4和R5彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
与一种或多种相同或不同的通式II的酚
其中取代基R7、R8、R9和R10彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
和/或与一种或多种相同或不同的通式I的四氢苯并噁嗪反应,
其中取代基R4也可以是式Z基团,和取代基R9也可以是式Z’基团
其中取代基R1、R2、R3、R5、R7、R8和R10各自定义如上,取代基R7也可以为衍生自通式I的四氢苯并噁嗪的基团,取代基R15为氢或衍生自通式I的四氢苯并噁嗪的基团,以及取代基R11和R12可相同或不同且各自为氢或C1-C10烷基,
以及其中取代基R2和R3或R3和R4或R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-一起也可以形成第二个四氢噁嗪环,或取代基R2和R3及R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-和-O-CH2-NR14-CH2-一起也可以形成第二和第三个四氢噁嗪环,其中R13和R14彼此独立地为在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
前提是:取代基R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14中的至少一个平均具有13~3000个碳原子且衍生自C2-C12烯烃的低聚物或聚合物,且R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14这组中的其余取代基,当它们是烃基时,各自具有1~20个碳原子。
所述的具有聚合物分布的多分散烃基-其平均具有13~3000个碳原子且衍生自C2-C12烯烃的低聚物或聚合物-是例如衍生自乙烯、丙烯、丁烯、异丁烯、苯乙烯、甲基苯乙烯、1-己烯、1-辛烯、1-癸烯或1-十二碳烯的那些。它们可以为均聚或共聚基团。它们的数均分子量Mn至少为183,它们的多分散指数PDI典型地为1.05~10。在Mn为183至约500的低分子量基团的情形下,它们还可以呈单分散形式存在。尤其令人感兴趣的是衍生自异丁烯的具有聚合物分布的多分散烃基。
本发明进一步提供通式III的低聚四氢苯并噁嗪和聚四氢苯并噁嗪
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,和
其中取代基R2、R3、R4和R5彼此独立地为氢原子或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,和
其中n为0~18的整数,
前提是:取代基R1、R3、R4或R5中的至少一个具有13~3000个碳原子,且R1、R3、R4或R5这组中的其余取代基,当它们是烃基时,在每种情形下具有1~20个碳原子。
本发明进一步提供通式IV的双环酚类化合物
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,和
其中取代基R2、R3、R4、R5、R7、R8、R9和R10彼此独立地为氢原子或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
前提是:取代基R1、R2、R3、R4、R5、R7、R8、R9和R10中的至少一个具有13~3000个碳原子,且R1、R2、R3、R4、R5、R7、R8、R9和R10这组中的其余取代基,当它们是烃基时,各自具有1~20个碳原子。
本发明进一步提供通式V的三环酚类化合物
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,
其中取代基R2、R3、R4、R5、R8、R9和R10彼此独立地为氢原子或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
其中取代基R9也可以是式Z’基团
其中取代基R7、R8和R10定义如上,取代基R7也可以为衍生自通式I的四氢苯并噁嗪的基团,取代基R15为氢或衍生自通式I的四氢苯并噁嗪的基团,以及取代基R11和R12可相同或不同且各自为氢或C1-C10烷基,和
前提是:取代基R1、R2、R3、R4、R5、R8、R9和R10中的至少一个具有13~3000个、优选26~3000个碳原子,且R1、R2、R3、R4、R5、R8、R9和R10这组中的其余取代基,当它们是烃基时,各自具有1~20个碳原子。
本发明将参照下述非限制性的实施例进行详细说明。
制备例
实施例1:通过将4-聚异丁烯基苯酚与3-甲基-6,8-二叔丁基四氢苯并噁嗪反应制备式Vb化合物
在室温下向500mL的四颈烧瓶中首先装入在100mL甲苯中的120g的4-聚异丁烯基苯酚(基于商业上可得的高反应性聚异丁烯Glissopal1000,Mn为1000)。快速加入52g的3-甲基-6,8-二叔丁基四氢苯并噁嗪。将烧瓶中的内容物加热至回流并在回流下搅拌2小时。在冷却到室温后,将烧瓶的内容物用甲醇洗涤并通过在150℃和5毫巴下蒸发而浓缩甲苯相。获得113g产物,为浅色透明的粘性油。
1H NMR(400MHz,16次扫描,CDCl3):
四氢苯并噁嗪信号(δ=4.70ppm,2H,-CH2-N(-CH3)-CH 2-O-;δ=3.82ppm,2H,-CH 2-N(-CH3)-CH2-O-;)和4-聚异丁烯基苯酚的一个邻位质子的信号(δ=6.70ppm)已经完全消失;苄基质子信号存在于δ=3.8-3.5ppm的范围,N-甲基的质子信号在δ=2.6-2.0ppm的范围,以及芳族质子信号在δ=6.9-7.2ppm的范围。
实施例2:
通过将4-聚异丁烯基苯酚与3-(二甲基氨基)丙基-6,8-二叔丁基四氢苯并噁嗪反应制备式Ve化合物
在室温下向1000mL的四颈烧瓶中首先装入在100mL甲苯中的170g的4-聚异丁烯基苯酚(基于商业上可得的高反应性聚异丁烯Glissopal1000,Mn为1000)。快速加入100g的3-(二甲基氨基)丙基-6,8-二叔丁基四氢苯并噁嗪。将烧瓶内容物加热至回流并在回流下搅拌2小时。在冷却到室温后,将烧瓶的内容物用甲醇洗涤并通过在90℃和5毫巴下蒸发而浓缩甲苯相。获得225g产物,为浅色透明的粘性油。
1H NMR(400MHz,16次扫描,CDCl3):
5-10%的残余四氢苯并噁嗪信号(δ=4.70ppm,2H,-CH2-N(-CH3)-CH 2-O-;δ=3.82ppm,2H,-CH 2-N(-CH3)-CH2-O-)和4-聚异丁烯基苯酚的一个邻位质子的少量残余信号(δ=6.70ppm)表明发生90~95%的转化;苄基质子信号存在于δ=3.8-3.4ppm的范围,N-甲基和N-亚甲基的质子信号在δ=2.6-2.0ppm的范围,芳族质子信号在δ=7.0-7.3ppm的范围。
实施例3:
通过将4-聚异丁烯基苯酚与3,6-二甲基-8-叔丁基四氢苯并噁嗪反应制备式Vc化合物
在室温下向1000mL的四颈烧瓶中首先装入在200mL甲苯中的240g的4-聚异丁烯基苯酚(基于商业上可得的高反应性聚异丁烯Glissopal1000,Mn为1000)。快速加入88g的3,6-二甲基-8-叔丁基四氢苯并噁嗪。将烧瓶内容物加热至回流并在回流下搅拌2小时。通过在150℃和5毫巴下蒸发而浓缩甲苯相。获得313g产物,为浅色透明的粘性油。
1H NMR(400MHz,16次扫描,CDCl3):
残余四氢苯并噁嗪信号(δ=4.70ppm,2H,-CH2-N(-CH3)-CH 2-O-;δ=3.82ppm,2H,-CH 2-N(-CH3)-CH2-O-)和4-聚异丁烯基苯酚的一个邻位质子的少量残余信号(δ=6.70ppm)表明发生80%的转化;苄基质子信号存在于δ=3.8-3.4ppm的范围,N-甲基的质子信号在δ=2.6-2.0ppm的范围,芳族质子信号在δ=7.0-7.3ppm的范围。
实施例4:
通过将3-甲基-6-聚异丁烯基四氢苯并噁嗪与3-甲基-6-叔丁基四氢苯并噁嗪反应制备式IIIv化合物
在室温下向500mL的蒸发器球管中首先装入在200mL甲苯中100g的3-甲基-6-聚异丁烯基四氢苯并噁嗪(基于商业上可得的高反应性聚异丁烯Glissopal1000,Mn为1000)。快速加入16.4g的3-甲基-6-叔丁基四氢苯并噁嗪。在旋转蒸发器中在100℃/5毫巴下馏除甲苯且将混合物在160℃/900毫巴下搅拌4小时。获得110g产物,为粘性油。
1H NMR(400MHz,16次扫描,CDCl3):
基于甲基质子的积分(苯并噁嗪:2.45-2.65ppm;2-羟基-苄基胺:2.05-2.30ppm),两个苯酚单元与一个苯并噁嗪相连。
实施例5:
通过将3-甲基-6-聚异丁烯基四氢苯并噁嗪与3-甲基-6-叔丁基四氢苯并噁嗪反应制备式IIIw化合物
在室温下向500mL的蒸发器球管中首先装入在200mL甲苯中的50g的3-甲基-6-聚异丁烯基四氢苯并噁嗪(基于商业上可得的高反应性聚异丁烯Glissopal1000,Mn为1000)。快速加入41g的3-甲基-6-叔丁基四氢苯并噁嗪。在旋转蒸发器中在100℃/5毫巴下馏除甲苯且将混合物在160℃/900毫巴下搅拌4小时。获得75g产物,为粘性油。
1H NMR(400MHz,16次扫描,CDCl3):
基于甲基质子的积分(苯并噁嗪:2.45-2.65ppm;2-羟基-苄基胺:2.05-2.30ppm),9个苯酚单元与1个苯并噁嗪相连。
实施例6:
通过将3-甲基-6-聚异丁烯基四氢苯并噁嗪和3-甲基-6,8-二叔丁基四氢苯并噁嗪与双酚A反应制备式VIc化合物
在1000mL的四颈烧瓶中,将130g的3-甲基-6-聚异丁烯基四氢苯并噁嗪(基于商业上可得的高反应性聚异丁烯Glissopal1000,Mn为1000)、78.5g的3-甲基-6,8-二叔丁基四氢苯并噁嗪、22.8g的双酚A和200mL的甲苯在回流下搅拌2小时。将烧瓶内容物在140℃和5毫巴下蒸发浓缩。获得194.5g产物,为浅色透明的粘性油。
1H NMR(400MHz,16次扫描,CDCl3):
5%的残余四氢苯并噁嗪信号(δ=4.70ppm,2H,-CH2-N(-CH3)-CH 2-O-;δ=3.82ppm,2H,-CH 2-N(-CH3)-CH2-O-)和双酚A的一个邻位质子的少量残余信号(δ=6.60ppm)表明发生95%的转化;苄基质子信号存在于δ=3.8-3.4ppm的范围,N-甲基的质子信号在δ=2.6-2.0ppm的范围,芳族质子信号在δ=6.7-7.3ppm的范围。
实施例7:通过将4-聚异丁烯基苯酚与3-(二甲基氨基)丙基-6-甲基-8-叔丁基四氢苯并噁嗪反应制备式Vn化合物
在室温下向1000mL的四颈烧瓶中首先装入在190g的Solvesso150(重质溶剂石脑油)中的300g的4-聚异丁烯基苯酚(基于商业上可得的高反应性聚异丁烯Glissopal1000,Mn为1000)。快速加入145g的3-(二甲基胺)丙基-6-甲基-8-叔丁基四氢苯并噁嗪。将烧瓶内容物在150℃下搅拌4小时。获得630g的产品的浅色透明溶液(固含量70%重量)。对于分析测定,将样品在150℃和3毫巴下通过蒸发浓缩。
1H NMR(400MHz,16次扫描,CDCl3):
残余的四氢苯并噁嗪信号(δ=4.80ppm,2H,-CH2-N(-CH3)-CH 2-O-;δ=3.91ppm,2H,-CH 2-N(-CH3)-CH2-O-)和4-聚异丁烯基苯酚的一个邻位质子的少量残余信号(δ=6.70ppm)表明发生90%的转化;苄基质子信号存在于δ=3.8-3.4ppm的范围,N-甲基质子信号在δ=2.6-2.0ppm的范围,芳族质子信号在δ=6.7-7.3ppm的范围。
应用实施例
实施例8:测试汽轮机燃料(喷气式发动机燃料)的热稳定性
使用根据DEF STAN 91-91和ASTM D 1655的规格Jet A-1的汽轮机燃料。在每种情形下使用100mg/l的来自制备例1~6的化合物进行添加。
在已经装有搅拌器、回流冷凝器和温度计的三颈烧瓶中,首先将5L的空气在室温下在1小时内通入150mL的待测燃料中。然后,将该燃料用油浴加热到140℃,并在该温度下再搅拌5小时。在冷却到室温后,使全部量的燃料滤过0.45μm的膜滤器。随后,在115℃下在烘箱中干燥45分钟并随后在减压下在干燥器中干燥2小时后,以重量分析方式测定滤渣:
空白实验值(无添加剂):8.9mg
根据本发明,在每种情形下以100mg/l的如下化合物进行添加剂添加:
式Vb化合物(制备例1):1.8mg
式Ve化合物(制备例2):1.0mg
式Vc化合物(制备例3):1.0mg
式IIIv化合物(制备例4):1.6mg
式IIIw化合物(制备例5):2.5mg
式VIc化合物(制备例6):1.0mg
根据本发明使用的添加剂的使用明显降低通过热应力在汽轮机燃料上形成的颗粒的量。
实施例9:汽轮机燃料(喷气式发动机燃料)的热稳定性的改进
使用根据DEF STAN 91-91和ASTM D 1655的规格Jet A-1的汽轮机燃料。根据ASTM D 3241的JFTOT折点方法测试热稳定性。对于未添加添加剂的汽轮机燃料,测定250℃的值。对于在每种情形下已用100mg/l的根据本发明使用的并列出在下面的添加剂添加的燃料,测得如下值:
式Vb化合物(制备例1):280℃
式Ve化合物(制备例2):260℃
式Vc化合物(制备例3):280℃
实施例10:测试汽轮机燃料的调水性
使用制备例1的式Vb化合物以及与实施例8和9相同的汽轮机燃料。
根据DIN 51415和ASTM D 1094,在加入100mg/L的式Vb化合物之后,测量汽轮机燃料的调水性,并因此测量不希望的形成乳液的倾向。为此,将80mL的添加了添加剂的汽轮机燃料和20mL的水以规定方式剧烈搅拌。之后,在各自1、5、30和60分钟之后,视觉评价相分离层。早在加入水之后5分钟,就得到燃料与水的完全分离;没有乳液部分留下。
实施例11:测试汽轮机燃料的水分离性能
使用符合根据DEF STAN 91-91和ASTM D 1655的规格Jet A-1的汽轮机燃料。根据ASTM D 3948(“MSEP”试验)测试汽轮机燃料关于它们的水分离性能的倾向。这些测量的特性特征是使用标准聚结过滤器,该过滤器测量燃料相的最终不透明度。在测量中,将根据本发明使用的添加剂与抗氧化剂2,6-二叔丁基-4-甲基苯酚(“BHT”)和金属减活剂N,N’-二亚水杨基-1,2-二氨基丙烷组合在常用于此目的的溶剂中测试。根据本发明使用的添加剂的剂量在每种情形下为215mg/L(基于它们的100%活性物质含量)。测得如下不透明性能的等级[0(最坏)~100(最好)的相对评估等级]:
空白值(无添加剂):98
式Vb化合物(制备例1):97
式Vc化合物(制备例3):98
与未添加添加剂的汽轮机燃料相比,没有发生劣化。
Claims (18)
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,和
其中取代基R2、R3、R4和R5彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
与一种或多种相同或不同的通式II的酚
其中取代基R7、R8、R9和R10彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
其中取代基R4也可以是式Z基团,和取代基R9也可以是式Z’基团
其中取代基R1、R2、R3、R5、R7、R8和R10各自定义如上,取代基R7也可以为衍生自通式I的四氢苯并嗪的基团,取代基R15为氢或衍生自通式I的四氢苯并嗪的基团,以及取代基R11和R12可相同或不同且各自为氢或C1-C10烷基,
以及其中取代基R2和R3或R3和R4或R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-一起也可以形成第二个四氢嗪环,或取代基R2和R3及R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-和-O-CH2-NR14-CH2-一起也可以形成第二和第三个四氢嗪环,其中R13和R14彼此独立地为在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
前提是:取代基R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14中的至少一个是数均分子量Mn为183~42000的聚异丁烯基,且R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14这组中的其余取代基,当它们是烃基时,各自具有1~20个碳原子。
2.根据权利要求1的用途,其中一个或两个数均分子量Mn为183~42000的聚异丁烯基出现在分子中作为取代基R1和/或R2和/或R4和/或R7和/或R9和/或R13和/或R14。
3.根据权利要求1的用途,其中R1、R2、R3、R4、R5、R7、R8、R9、R10、R13和R14这组中的不是数均分子量Mn为183~42 000的聚异丁烯基的其余取代基彼此独立地为氢原子、羟基或当它们是烃基时,为线性或支化C1-C4烷基。
4.根据权利要求2的用途,其中R1、R2、R3、R4、R5、R7、R8、R9、R10、R13和R14这组中的不是数均分子量Mn为183~42000的聚异丁烯基的其余取代基彼此独立地为氢原子、羟基或当它们是烃基时,为线性或支化C1-C4烷基。
5.根据权利要求1的用途,其中所述多环酚类化合物的数均分子量Mn为285~25000。
6.根据权利要求2的用途,其中所述多环酚类化合物的数均分子量Mn为285~25000。
7.根据权利要求3的用途,其中所述多环酚类化合物的数均分子量Mn为285~25000。
8.根据权利要求1的用途,其中多环酚类化合物中的聚异丁烯基的平均多分散指数PDI是母体四氢苯并嗪I和/或酚II中的聚异丁烯基的平均多分散指数PDI的至多5倍。
10.根据权利要求1~9任一项的用途,是在汽轮机燃料中作为抗氧化剂。
11.根据权利要求10的用途,是作为抗氧化剂用于改进汽轮机燃料的热稳定性。
12.一种汽轮机燃料组合物,其包含汽轮机燃料和至少一种如权利要求1-9任一项所定义的多环酚类化合物。
13.一种用于汽轮机燃料的添加剂浓缩物,其包含至少一种如权利要求1-9任一项所定义的多环酚类化合物和如果合适的话,至少一种稀释剂和如果合适的话,至少一种添加剂。
14.根据权利要求1~9任一项的用途,是作为抗氧化剂用于改进润滑剂组合物的氧化和老化稳定性和/或用于改进润滑剂组合物的剪切稳定性。
15.每个分子具有至多20个苯环且可通过下述方式获得的多环酚类化合物:
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,和
其中取代基R2、R3、R4和R5彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
与一种或多种相同或不同的通式II的酚
其中取代基R7、R8、R9和R10彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
其中取代基R4也可以是式Z基团,和取代基R9也可以是式Z’基团
其中取代基R1、R2、R3、R5、R7、R8和R10各自定义如上,取代基R7也可以为衍生自通式I的四氢苯并嗪的基团,取代基R15为氢或衍生自通式I的四氢苯并嗪的基团,以及取代基R11和R12可相同或不同且各自为氢或C1-C10烷基,
以及其中取代基R2和R3或R3和R4或R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-一起也可以形成第二个四氢嗪环,或取代基R2和R3及R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-和-O-CH2-NR14-CH2-一起也可以形成第二和第三个四氢嗪环,其中R13和R14彼此独立地为在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
前提是:取代基R1、R2、R3、R5、R7、R8、R10、R13或R14中的至少一个具有26~3000个碳原子,且R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14这组中的其余取代基,当它们是烃基时,各自具有1~20个碳原子。
16.每个分子具有至多20个苯环且可通过下述方式获得的多环酚类化合物:
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,和
其中取代基R2、R3、R4和R5彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
与一种或多种相同或不同的通式II的酚
其中取代基R7、R8、R9和R10彼此独立地为氢原子、羟基或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
其中取代基R4也可以是式Z基团,和取代基R9也可以是式Z’基团
其中取代基R1、R2、R3、R5、R7、R8和R10各自定义如上,取代基R7也可以为衍生自通式I的四氢苯并嗪的基团,取代基R15为氢或衍生自通式I的四氢苯并嗪的基团,以及取代基R11和R12可相同或不同且各自为氢或C1-C10烷基,
以及其中取代基R2和R3或R3和R4或R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-一起也可以形成第二个四氢嗪环,或取代基R2和R3及R4和R5与连在苯环上的亚结构-O-CH2-NR13-CH2-和-O-CH2-NR14-CH2-一起也可以形成第二和第三个四氢嗪环,其中R13和R14彼此独立地为在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
前提是:取代基R1、R2、R3、R5、R7、R8、R10、R13或R14中的至少一个平均具有13~3000个碳原子且衍生自C2-C12烯烃的低聚物或聚合物,且R1、R2、R3、R4、R5、R7、R8、R9、R10、R13或R14这组中的其余取代基,当它们是烃基时,各自具有1~20个碳原子。
18.通式V的三环酚类化合物
其中取代基R1为具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6是氢原子或C1-C4烷基,
其中取代基R2、R3、R4、R5、R8、R9和R10彼此独立地为氢原子或在每种情形下具有1~3000个碳原子且可被一个或多个选自O和S的杂原子和/或被一个或多个NR6基团间隔的烃基,其中R6定义如上,
其中取代基R9也可以是式Z’基团
其中取代基R7、R8和R10定义如上,取代基R7也可以为衍生自通式I的四氢苯并嗪的基团,取代基R15为氢或衍生自通式I的四氢苯并嗪的基团,以及取代基R11和R12可相同或不同且各自为氢或C1-C10烷基,和
前提是:取代基R1、R2、R3、R4、R5、R8、R9和R10中的至少一个具有13~3000个碳原子,且R1、R2、R3、R4、R5、R8、R9和R10这组中的其余取代基,当它们是烃基时,各自具有1~20个碳原子。
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