CN106190473A - 一种含氮六元环结构硼酸酯制动液的制备方法 - Google Patents
一种含氮六元环结构硼酸酯制动液的制备方法 Download PDFInfo
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- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 239000012530 fluid Substances 0.000 title claims abstract description 39
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 238000005260 corrosion Methods 0.000 claims abstract description 12
- 230000007797 corrosion Effects 0.000 claims abstract description 12
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 11
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 11
- 239000003085 diluting agent Substances 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 239000004327 boric acid Substances 0.000 claims abstract description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 239000010695 polyglycol Substances 0.000 claims description 7
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 6
- 229920000151 polyglycol Polymers 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- 239000012964 benzotriazole Substances 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 238000005457 optimization Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 10
- 238000009835 boiling Methods 0.000 abstract description 6
- 150000002148 esters Chemical class 0.000 abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 229910052796 boron Inorganic materials 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- -1 boric acid ester Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- SODVHULTPGWIOJ-UHFFFAOYSA-N B(O)(O)OCCOCCOC Chemical compound B(O)(O)OCCOCCOC SODVHULTPGWIOJ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
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- 239000012467 final product Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
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- C10M2207/02—Hydroxy compounds
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- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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Abstract
本发明公开一种含氮六元环结构硼酸酯制动液的制备方法,此制动液包括硼酸酯、稀释剂、缓蚀剂和抗氧剂,其中硼酸酯为含氮六元环结构,它是以环已胺、水杨醛反应脱水产物再与硼酸、十个碳以上的正醇酯化反应后的产物。本发明的优点在于产品分子结构中引入了氮原子并形成了稳定的六元环内配体,分子中引入了长碳链,并形成三酯,空间位阻增大,有利于阻碍水分子的进攻,从而提高了其抗水解性,由其制备的制动液具有较高的干、湿沸点和合适的低温粘度,有利于延长发动机使用寿命。
Description
技术领域
本发明涉及制动液领域,具体说是抗水解能力强、含氮六元环结构硼酸酯制动液的制备方法。
背景技术
机动车辆制动液也俗称汽车刹车油,是用于汽车液压制动系统中传递压力,使车轮制动器实现制动作用的一种功能液体,它具有传递动能、散热、防锈防腐和润滑减摩等作用,它的发展也已历经了几个阶段。随着现代汽车工业的发展和人们对于安全性能的逐步认知,研制具有高的干、湿平衡回流沸点和低的低温粘度的新一代合成制动液成了制动液研究的热点,而其中酯型特别是硼酸酯型制动液除具有普通制动液的一般性能特点外,还具有环保、无毒、平衡回流沸点高,较低的低温粘度,良好的橡胶适应性能和对金属零部件腐蚀性较低等优点,同时和醇醚型制动液具有较好的相容性。
但是,因硼酸酯中B原子具有空的SP2杂化轨道,易被含有未共用电子对的亲核试剂进攻。另一方面水分子中含有未共用电子对,可攻击硼酸酯中的B原子,使其发生水解,因此其抗水解性较差。如专利公开号CN104611092A高级机动车制动液组合物,专利公开号CN102618354A一种硼酸酯型合成制动液制备方法等均为醇醚型硼酸酯,但其抗水解性能还有待提高。
因此,如何解决硼酸酯的水解稳定性是技术工作者的研究方向,特别是硼酸酯作为润滑油脂的极压抗磨剂使用时。经研究发现,含氮的硼酸酯是一类防锈、抗氧化、高温稳定、减摩抗摩性能优良的润滑油添加剂,由于取代基团中氮原子上的孤对电子可以与硼原子的空轨道配位形成N→B配位健,从而提高了硼酸酯的水解稳定性,而含氮硼酸酯的防锈性和抗氧化性也都得到明显改善。进一步的研究发现,含氮六元环的硼酸酯既利用了含孤对电子的物质与硼酸酯中的硼原子配位占据其空轨道形成六元环内配体,有利于提高其抗磨减摩性能,又改变了硼酸酯的结构增加了其空间位阻,使水分子更不易进攻硼原子的空轨道,是水解稳定性最好的一种结构,沈光球、郑直《有机硼酸酯添加剂的水解稳定性及摩擦特性》,胡晓兰、梁国正的《硼酸酯水解稳定性研究与应用》等的研究在作为润滑油的添加剂上得到了验证。
专利公开号CN102796600A一种高级硼酸酯型汽车制动液的制备方法中,以1,3丙三醇与硼酸酯化得到六元环状丙醇丙醚硼酸酯,形成O→B配位键,而O原子的配位能力远不如N原子,水解能力不能得到明显改善;而公开号CN104152223A一种含氮结构的硼酸酯型制动液的制备方法中,虽然氮原子与硼原子形成了配位键,但没有形成稳定的六元环结构,必须外加胺类抗水解稳定剂,而且其低温运动粘度(—40℃)为1561mm2/s,未达到国标GB12981-2012的要求。
发明内容
本发明的目的是提供一种抗水解能力强的含氮六元环结构硼酸酯制动的液制备方法。
本发明一种含氮六元环结构硼酸酯制动液是这样实现的,按重量份配比包括:
硼酸酯 40~70份
稀释剂 10~50份
缓蚀剂 0.1~5份
抗氧剂 0.01~2份。
所述的硼酸酯为含氮六元环结构的硼酸酯,其结构式为:C6H4CHNC6H9OB-(O-CnHn+1)2(以下简称NB)。
所述的含氮六元环结构的硼酸酯NB是这样实现的:
(1)环已胺和水杨醛以1.3:1.0摩尔比混合于装有回流冷凝器的加热装置中,在100~105℃反应1~2小时,反应过程中以0.01~0.05MPa真空度减压蒸馏去掉反应中的水分,得到产物NA;
(2)将步骤1产物NA、硼酸和CnHn+1OH(正醇)按1:1:2摩尔比在上述装置中继续加热到100~110℃反应2~4小时,反应过程中以0.01~0.05MPa真空度减压蒸馏去掉反应中的水分,即得到含氮六元环结构的硼酸酯产物NB。
所述的CnHn+1OH(正醇)其n值为6~20,更优选n值为9~18,最优选n值为12~14。
所述的稀释剂为聚乙二醇醚与三乙二醇单甲醚、三乙二醇单丁醚、四乙二醇单甲醚中的至少一种组合,按重量份配比为2~5:1。
所述的聚乙二醇醚的分子量范围为200~600,更优选的分子量范围为200~400,最优选的范围为200~300。
所述的抗氧剂为二烷基化二苯胺与2,6-二叔丁基对甲酚、2,6-二叔丁基-4-仲丁基苯酚中的至少一种组合,按重量份配比为1:1~4。
所述的缓蚀剂为苯并三氮唑与三乙醇胺、环已胺中的至少一种组合,按重量份配比为1:3~8。
本发明一种含氮六元环结构硼酸酯制动液的制备方法如下:
按重量份配比,将以上所述硼酸酯、稀释剂、缓蚀剂和抗氧剂加入上述装置中,加热到90~110℃搅拌1小时,加热搅拌过程中以0.01~0.05MPa负压抽真空,冷却降温,过滤,即得到含氮六元环结构硼酸酯制动液。
本发明一种含氮六元环结构硼酸酯制动液,与现有技术相比,具有如下特点和优势:
1、环已胺作为引入氮原子的核心物质,同时作为缓蚀剂使用,全程参与反应和作用,该物质投加量比化学计算量有一定的过量,是为了使整个反应更完全,过量部分可以起到带水剂和pH调节剂的作用,做到一物多用;
2、本发明一种含氮六元环结构硼酸酯因分子结构中引入了氮原子并形成了稳定的六元环内配体,在提高其抗磨减摩性能的基础上,分子中引入了长碳链,并形成三酯,空间位阻增大,有利于阻碍水分子的进攻,从而更加提高了其抗水解性,由其制备的制动液具有较高的干、湿沸点和合适的低温粘度;
3、因该种结构硼酸酯的抗水解能力强,大大增加了所制备制动液产品的使用寿命;
4、制备过程中加热抽真空可以进一步除去所有材料中残余的水分和低分子量物质,可以保证产品具有高的干、湿沸点的同时还具有较低的低温粘度。
具体实施方式
以下实施例对本发明进行说明,但本发明并不受这些实施例所限制,对本发明的具体实施方式进行修改或者对部分技术特征进行等同替换,而不脱离本发明方案的精神,其均应涵盖在本发明请求保护的技术方案范围当中。
实施例1
(1)取环已胺129份、水杨醛122份 混合于装有回流冷凝器的加热装置中,在100~105℃反应2小时,反应过程中以0.01~0.05MPa真空度减压蒸馏去反应中的水分,得到产物NA;
(2)在步骤1产物NA中加入硼酸62份和正十二醇(C12H25OH)373份 ,在上述装置中继续加热到100~110℃反应2~4小时,反应过程中以0.01~0.05MPa真空度减压蒸馏除去反应中的水分,即得到含氮六元环结构的硼酸酯产物NB;
(3)含氮六元环结构硼酸酯制动液的制备:在步骤2产物NB中加入稀释剂三乙二醇单丁醚82份,聚乙二醇醚427份,缓蚀剂苯并三氮唑5.4份,三乙醇胺33.5份,抗氧剂二烷基化二苯胺1.96份,2,6-二叔丁基对甲酚1.1份,加热到90~110℃搅拌1小时,加热搅拌过程中以0.01~0.05MPa负压抽真空,冷却降温,过滤,即得到含氮六元环结构硼酸酯制动液。
实施例2
步骤(1)、(2)同实施例1,在如上硼酸酯产物NB中加入稀释剂三乙二醇单丁醚46.2份,聚乙二醇醚235份,缓蚀剂苯并三氮唑1.2份,三乙醇胺7.45份,抗氧剂二烷基化二苯胺3.94份,2,6-二叔丁基对甲酚2.0份,加热到90~110℃搅拌1小时,加热搅拌过程中以0.01~0.05MPa负压抽真空,冷却降温,过滤,即得到含氮六元环结构硼酸酯制动液。
实施例3
步骤(1)、(2)同实施例1,在如上硼酸酯产物NB中加入稀释剂三乙二醇单丁醚66份,聚乙二醇醚336份,缓蚀剂苯并三氮唑5.4份,三乙醇胺33.5份,抗氧剂二烷基化二苯胺1.96份,2,6-二叔丁基对甲酚1.1份,加热到90~110℃搅拌1小时,加热搅拌过程中以0.01~0.05MPa负压抽真空,冷却降温,过滤,即得到含氮六元环结构硼酸酯制动液。
比较例4
在装有回流冷凝器的加热装置中加入二乙二醇单甲醚硼酸酯650份,再加入稀释剂三乙二醇单丁醚66份,聚乙二醇醚336份,缓蚀剂苯并三氮唑5.4份,三乙醇胺33.5份,抗氧剂二烷基化二苯胺1.96份,2,6-二叔丁基对甲酚1.1份,加热到90~110℃搅拌1小时,加热搅拌过程中以0.01~0.05MPa负压抽真空,冷却降温,过滤,即得到醇醚硼酸酯制动液。
以上所有实施例和对比例产品按GB12981-2012机动车辆制动液标准中HZY4的主要相关项目进行检测,并增加抗水解稳定性试验,试验检测数据如表1所示。
抗水解稳定性试验(敞口观察法):取干燥的25mL玻璃杯,各加入10mL w(含氮硼酸酯)=1.0%的石蜡油溶液,置于湿度50%的室内,观察液体开始变混浊的时间(混浊表明硼酸酯已分解生成不溶于石蜡油的固态硼酸等物质)。
表1
由表1可看出,本发明一种含氮六元环结构硼酸酯制动液与现有技术(比较例 4)相比,具有较高的干、湿沸点,较低的低温粘度,且大幅度提高了其抗水解性,有利于延长发动机使用寿命。
Claims (10)
1.一种含氮六元环结构硼酸酯制动液,其特征在于,按重量份配比包括:
硼酸酯 40~70份
稀释剂 10~50份
缓蚀剂 0.1~5份
抗氧剂 0.01~2份。
2.如权利要求1所述的一种含氮六元环结构硼酸酯制动液,其特征在于,所述的硼酸酯为含氮六元环结构的硼酸酯,其结构式为:C6H4CHNC6H9OB-(O-CnHn+1)2(以下简称NB)。
3.如权利要求2所述的一种含氮六元环结构硼酸酯制动液,其特征在于,所述的含氮六元环结构的硼酸酯NB是这样实现的:
(1)环已胺和水杨醛以1.3:1.0摩尔比混合于装有回流冷凝器的加热装置中,在100~105℃反应1~2小时,反应过程中以0.01~0.05MPa真空度减压蒸馏去反应中的水分,得到产物NA;
(2)将步骤1产物NA、硼酸和CnHn+1OH(正醇)按1:1:2摩尔比在上述装置中继续加热到100~110℃反应2~4小时,反应过程中以0.01~0.05MPa真空度减压蒸馏去反应中的水分,即得到含氮六元环结构的硼酸酯产物NB。
4.如权利要求3所述的一种含氮六元环结构硼酸酯制动液,其特征在于,所述的CnHn+1OH(正醇)其n值为6~20,更优选n值为9~18,最优选n值为12~14。
5.如权利要求1所述的一种含氮六元环结构硼酸酯制动液,其特征在于,所述的稀释剂为三乙二醇单甲醚、三乙二醇单丁醚、四乙二醇单甲醚中的至少一种与聚乙二醇醚的组合,按重量份配比为1:2~5。
6.如权利要求5所述的一种含氮六元环结构硼酸酯制动液,其特征在于,所述的聚乙二醇醚的分子量范围为200~600。
7.如权利要求6所述的一种含氮六元环结构硼酸酯制动液,其特征在于,所述的聚乙二醇醚分子量更优化的范围为200~400,最优化的范围为200~300。
8.如权利要求1所述的一种含氮六元环结构硼酸酯制动液,其特征在于,所述的抗氧剂为二烷基化二苯胺与2,6-二叔丁基对甲酚、2,6-二叔丁基-4-仲丁基苯酚中的至少一种组合,按重量份配比为1:1~4。
9.如权利要求1所述的一种含氮六元环结构硼酸酯制动液,其特征在于,缓蚀剂为苯并三氮唑与三乙醇胺、环已胺中的至少一种组合,按重量份配比为1:3~8。
10.如权利要求1所述的一种含氮六元环结构硼酸酯制动液的制备方法,其特征在于,包括如下步骤:将以上所述硼酸酯、稀释剂、缓蚀剂和抗氧剂按比例加入上述装置中,加热到90~110℃搅拌1小时,加热搅拌过程中以0.01~0.05MPa负压抽真空,冷却降温,过滤,即得到含氮六元环结构硼酸酯制动液。
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