CN108503550A - 一种离子液体型抗静电剂及其制备方法 - Google Patents

一种离子液体型抗静电剂及其制备方法 Download PDF

Info

Publication number
CN108503550A
CN108503550A CN201810436740.8A CN201810436740A CN108503550A CN 108503550 A CN108503550 A CN 108503550A CN 201810436740 A CN201810436740 A CN 201810436740A CN 108503550 A CN108503550 A CN 108503550A
Authority
CN
China
Prior art keywords
antistatic agent
ionic liquid
preparation
formula
precursor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201810436740.8A
Other languages
English (en)
Inventor
陆园
于英豪
宫青海
蔡智奇
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
New Special Road Yantai New Mstar Technology Ltd
Original Assignee
New Special Road Yantai New Mstar Technology Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by New Special Road Yantai New Mstar Technology Ltd filed Critical New Special Road Yantai New Mstar Technology Ltd
Priority to CN201810436740.8A priority Critical patent/CN108503550A/zh
Publication of CN108503550A publication Critical patent/CN108503550A/zh
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62Quaternary ammonium compounds
    • C07C211/63Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/02Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/06Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127Preparation from compounds containing pyridine rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20Quaternary compounds thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/54Quaternary phosphonium compounds
    • C07F9/5407Acyclic saturated phosphonium compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00Materials not provided for elsewhere
    • C09K3/16Anti-static materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明涉及一种离子液体型抗静电剂及其制备方法。该方法是通过两种离子型前驱体化合物A和B通过离子液体交换得到目标产物离子液体型抗静电剂。本发明所制备的离子型抗静电剂具有蒸汽压极低,不可燃,电导率高;且制备工艺简单,转化率高,选择性好,利于中试放大及大规模工业化生产;具有良好的热稳定性和化学稳定性,在使用过程中不影响塑料制品的其他性质(如拉伸性能、冲击性能等机械性能,透明性、着色性等表观性能);且易于后处理,不会对环境造成污染等优点。

Description

一种离子液体型抗静电剂及其制备方法
技术领域
本发明属于工程塑料行业中抗静电剂的设计与开发领域,具体涉及一种 离子液体型抗静电剂及其制备方法。
背景技术
由于塑料制品具有重量轻、成本低以及良好的可塑性、绝缘性、抗腐蚀 性等特点,近年来已被广泛应用于电子电气、汽车、建筑、家电、医疗、办 公设备、机械、航空航天等众多领域。在“以塑代钢”、“以塑代木”的发展 趋势下,塑料行业已成为当今世界工业中增长速度较快的领域,其发展不仅 对国家支柱产业和现代高新技术产业起着支撑作用,同时也推动传统产业改 造和产品结构的调整。
同时,我们应该注意到的是:塑料通常具有很好的电绝缘性,既不能电 离,又不能传递电子。在其加工和使用过程中,当同其它物体或自身接触和摩 擦时,会因电子的得失而带电,并且很难通过传导而消失,从而产生静电。由于 静电吸引力,塑料制品会吸附空气中的灰尘,影响制品美观;电影胶片和唱 片由于静电吸尘会使清晰度和音质变劣。另外,静电还会导致精密仪器失真, 电子元件报废等,从而带来巨大损失,如在美国塑料电子部件在储运过程中 废品率达到50%,损失高达50亿美元。静电甚至会危及人的生命,有些塑 料制品产生的静电电压高达几千伏,人一旦接触就会触电,严重时会造成死 亡。因此,研究开发经济高效的抗静电剂具有十分重要的经济意义和社会意 义。
常用的抗静电剂多为表面活性剂类,可以分为:非离子型、阳离子型和 阴离子型。非离子型抗静电剂虽然具有热稳定性良好、价格较便宜、使用方 便等优点,但是因自身不带电荷,故抗静电性能都比不上离子型抗静电剂, 所以其所需添加量较大。阴离子型抗静电剂具有热稳定性高的优点,但吸湿 性大、加工困难、透明性能差等缺点也较为明显。阳离子型抗静电剂抗静电 的效果最好,吸附能力强,耐摩擦及洗涤,但是其不耐高温,这也严重限制 了阳离子型抗静电剂的实际应用。
因此,有必要提出有效的技术方案,解决上述问题。
发明内容
本发明针对上述现有技术的不足,提供一种离子液体型抗静电剂的制备 方法。该方法得到的离子液体型抗静电剂产品性能优良。
本发明解决上述技术问题的技术方案如下:
一种离子液体型抗静电剂的制备方法,步骤如下:
(1)采用具有式(a)结构的季铵阳离子、具有式(b)结构的季膦阳 离子、具有式(c)结构的咪唑阳离子和具有式(d)结构的吡啶阳离子结构 中的一种的卤化物作为前驱体A;
式中R1、R2、R3、R4为氢原子或烷基取代基;
(2)采用具有[BF4]-、[PF6]-、[CF3SO3]-和[Tf2N]-阴离子中的一种的金 属盐作为前驱体B;
(3)将所述前驱体A和前驱体B按照一定的摩尔比混合,再加入一定 量的水,在一定温度下恒温搅拌一段时间,静置后溶液分为两相,除去上层 水相,再将下层粘稠液体用水洗涤,最后在一定温度下真空干燥即可得到目 标产物离子液体型抗静电剂。
优选地,所述的阳离子中烷基取代基的烷基链长度为C1~C16
优选地,所述的前驱体A中卤化物为Cl-、Br-或I-,优选Br-
优选地,所述的前驱体B中金属盐为Li+、Na+或K+,优选Li+、Na+
优选地,所述的前驱体A和前驱体B的摩尔比为1:1.1。
优选地,所述的前驱体A和前驱体B反应温度为50~70℃,反应时间 为8~12h。
优选地,所述的真空干燥温度为90℃,干燥时间为12h。
本发明还提供一种离子液体型抗静电剂,所述离子液体型抗静电剂的阳 离子为具有式(a)结构的季铵阳离子、具有式(b)结构的季膦阳离子、具 有式(c)结构的咪唑阳离子、具有式(d)结构的吡啶阳离子中的一种,
式中R1、R2、R3、R4为氢原子或烷基取代基;
所述离子液体型抗静电剂的阳离子为[BF4]-、[PF6]-、[CF3SO3]-、[Tf2N]-中的一种。
本发明所制备的离子型抗静电剂具有如下优点:
(1)蒸汽压极低,不可燃,电导率高;且制备工艺简单,转化率高, 选择性好,利于中试放大及大规模工业化生产。
(2)具有良好的热稳定性和化学稳定性,在使用过程中不影响塑料制 品的其他性质(如拉伸性能、冲击性能等机械性能,透明性、着色性等表观 性能);且易于后处理,不会对环境造成污染。
具体实施方式
下面结合实施例对本发明作进一步地详细说明,但本发明的实施方式不 限于此。对于未特别注明的工艺参数,可参照常规技术进行。
实施例1
本实施例提供了一种离子液体型抗静电剂的制备方法,该制备方法具体 包括以下步骤:
将0.1mol三丁基甲基溴化铵与0.11mol双(三氟甲磺酰亚胺)锂加入 到装有回流装置的三口圆底烧瓶中,再加入500mL水,在70℃下恒温磁力 搅拌12h。静置后溶液分为两相,下层为离子液体型抗静电剂相,上层为水 相,用分液漏斗进行分离,再将下层离子液体型抗静电剂相反复用水洗涤, 直到用AgNO3滴定不再有沉淀产生,然后旋转蒸发去除水,最后在90℃下 真空干燥12h,即可得到目标产物离子液体型抗静电剂。
实施例2
本实施例提供了一种离子液体型抗静电剂的制备方法,该制备方法具体 包括以下步骤:
将0.1mol三丁基甲基溴化鏻与0.11mol四氟硼酸钠加入到装有回流装 置的三口圆底烧瓶中,再加入500mL水,在50℃下恒温磁力搅拌12h。静 置后溶液分为两相,下层为离子液体型抗静电剂相,上层为水相,用分液漏 斗进行分离,再将下层离子液体型抗静电剂相反复用水洗涤,直到用AgNO3滴定不再有沉淀产生,然后旋转蒸发去除水,最后在90℃下真空干燥12h, 即可得到目标产物离子液体型抗静电剂。
实施例3
本实施例提供了一种离子液体型抗静电剂的制备方法,该制备方法具体 包括以下步骤:
将0.1mol1-十六烷基3-甲基咪唑溴盐与0.11mol双(三氟甲磺酰亚胺) 锂加入到装有回流装置的三口圆底烧瓶中,再加入500mL水,在60℃下恒 温磁力搅拌8h。静置后溶液分为两相,下层为浅黄色油状液体——离子液 体型抗静电剂相,上层为水相。冷却后,下层为白色固体相,将水除去,并 用水对固体相进行反复冲洗,直到用AgNO3滴定不再有沉淀产生,得到的 白色固体最后在90℃下真空干燥12h,即可得到目标产物离子液体型抗静电剂,并用适量乙醇溶解待用。
实施例4
本实施例提供了一种离子液体型抗静电剂的制备方法,该制备方法具体 包括以下步骤:
将0.1mol1-丁基吡啶与0.11mol六氟硼酸钠加入到装有回流装置的三 口圆底烧瓶中,再加入500mL水,在70℃下恒温磁力搅拌12h。静置后溶 液分为两相,下层为离子液体型抗静电剂相,上层为水相,用分液漏斗进行 分离,再将下层离子液体型抗静电剂相反复用水洗涤,直到用AgNO3滴定 不再有沉淀产生,然后旋转蒸发去除水,最后在90℃下真空干燥12h,即可 得到目标产物离子液体型抗静电剂。
实施例5
本实施例提供了一种离子液体型抗静电剂的制备方法,该制备方法具体 包括以下步骤:
将0.1mol 1-丁基-3-甲基咪唑溴盐与0.11mol三氟磺酸钠加入到装有回 流装置的三口圆底烧瓶中,再加入500mL水,在70℃下恒温磁力搅拌12h。 静置后溶液分为两相,下层为离子液体型抗静电剂相,上层为水相,用分液 漏斗进行分离,再将下层离子液体型抗静电剂相反复用水洗涤,直到用AgNO3滴定不再有沉淀产生,然后旋转蒸发去除水,最后在90℃下真空干 燥12h,即可得到目标产物离子液体型抗静电剂。
实施例6
本实施例提供了一种离子液体型抗静电剂的制备方法,该制备方法具体 包括以下步骤:
将0.1mol 1-丁基-3-甲基咪唑溴盐与0.11mol双(三氟甲磺酰亚胺)锂 加入到装有回流装置的三口圆底烧瓶中,再加入500mL水,在60℃下恒温 磁力搅拌8h。静置后溶液分为两相,下层为离子液体型抗静电剂相,上层 为水相,用分液漏斗进行分离,再将下层离子液体型抗静电剂相反复用水洗 涤,直到用AgNO3滴定不再有沉淀产生,然后旋转蒸发去除水,最后在90℃ 下真空干燥12h,即可得到目标产物离子液体型抗静电剂。
上述实施例为本发明较佳的实施方式,但本发明的实施方式并不受上述 实施例的限制,其他的任何未背离本发明的精神实质与原理下所作的改变、 修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护 范围之内。

Claims (8)

1.一种离子液体型抗静电剂的制备方法,其特征在于,步骤如下:
(1)采用具有式(a)结构的季铵阳离子、具有式(b)结构的季膦阳离子、具有式(c)结构的咪唑阳离子和具有式(d)结构的吡啶阳离子结构中的一种的卤化物作为前驱体A;
式中R1、R2、R3、R4为氢原子或烷基取代基;
(2)采用具有[BF4]-、[PF6]-、[CF3SO3]-和[Tf2N]-阴离子中的一种的金属盐作为前驱体B;
(3)将所述前驱体A和前驱体B按照一定的摩尔比混合,再加入一定量的水,在一定温度下恒温搅拌一段时间,静置后溶液分为两相,除去上层水相,再将下层粘稠液体用水洗涤,最后在一定温度下真空干燥即可得到目标产物离子液体型抗静电剂。
2.如权利要求1所述的制备方法,其特征在于,所述的阳离子中烷基取代基的烷基链长度为C1~C16
3.如权利要求1所述的制备方法,其特征在于,所述的前驱体A中卤化物为Cl-、Br-或I-
4.如权利要求1所述的制备方法,其特征在于,所述的前驱体B中金属盐为Li+、Na+或K+
5.如权利要求1所述的制备方法,其特征在于,所述的前驱体A和前驱体B的摩尔比为1:1.1。
6.如权利要求1所述的制备方法,其特征在于,所述的前驱体A和前驱体B反应温度为50~70℃,反应时间为8~12h。
7.如权利要求1所述的制备方法,其特征在于,所述的真空干燥温度为90℃,干燥时间为12h。
8.一种离子液体型抗静电剂,其特征在于,所述离子液体型抗静电剂的阳离子为具有式(a)结构的季铵阳离子、具有式(b)结构的季膦阳离子、具有式(c)结构的咪唑阳离子、具有式(d)结构的吡啶阳离子中的一种,
式中R1、R2、R3、R4为氢原子或烷基取代基;
所述离子液体型抗静电剂的阳离子为[BF4]-、[PF6]-、[CF3SO3]-、[Tf2N]-中的一种。
CN201810436740.8A 2018-05-09 2018-05-09 一种离子液体型抗静电剂及其制备方法 Pending CN108503550A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810436740.8A CN108503550A (zh) 2018-05-09 2018-05-09 一种离子液体型抗静电剂及其制备方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810436740.8A CN108503550A (zh) 2018-05-09 2018-05-09 一种离子液体型抗静电剂及其制备方法

Publications (1)

Publication Number Publication Date
CN108503550A true CN108503550A (zh) 2018-09-07

Family

ID=63400069

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810436740.8A Pending CN108503550A (zh) 2018-05-09 2018-05-09 一种离子液体型抗静电剂及其制备方法

Country Status (1)

Country Link
CN (1) CN108503550A (zh)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109796723A (zh) * 2019-01-30 2019-05-24 杭州师范大学 一种抗静电、耐摩擦和耐磨损聚甲醛材料及其制备方法
CN110172031A (zh) * 2019-05-23 2019-08-27 北京师范大学 一种阴离子型n-取代苯胺离子液体及其制备方法
CN115650887A (zh) * 2022-10-25 2023-01-31 默尼化工科技(上海)有限公司 一种光学透明耐温长效小分子型抗静电剂及其制备方法和应用
CN115894933A (zh) * 2022-12-07 2023-04-04 世晨材料技术(上海)有限公司 一种有机硅材料用反应型抗静电剂化合物
CN116041708A (zh) * 2022-12-07 2023-05-02 世晨材料技术(上海)有限公司 一种反应型有机硅材料用抗静电剂化合物的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014092953A1 (en) * 2012-12-14 2014-06-19 Exxonmobil Research And Engineering Company Ionic liquids as lubricating oil base stocks, cobase stocks and multifunctional functional fluids
CN106632483A (zh) * 2016-12-20 2017-05-10 青岛辰达生物科技有限公司 一种替诺福韦二吡呋酯的制备方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014092953A1 (en) * 2012-12-14 2014-06-19 Exxonmobil Research And Engineering Company Ionic liquids as lubricating oil base stocks, cobase stocks and multifunctional functional fluids
CN106632483A (zh) * 2016-12-20 2017-05-10 青岛辰达生物科技有限公司 一种替诺福韦二吡呋酯的制备方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANTHONY K.BURRELL ET AL.: "The large scale synthesis of pure imidazolium and pyrrolidinium ionic liquids", 《GREEN CHEMISTRY》 *
GABI THIELEMANN ET AL.: "Polarity of tetraalkylammonium-based ionic liquids and related low temperature molten salts", 《NEW J.CHEM.》 *
REBECCA K.BLUNDELL ET AL.: "Quaternary ammonium and phosphonium based ionic liquids:a comparison of common anions", 《PHYS.CHEM.CHEM.PHYS.》 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109796723A (zh) * 2019-01-30 2019-05-24 杭州师范大学 一种抗静电、耐摩擦和耐磨损聚甲醛材料及其制备方法
CN109796723B (zh) * 2019-01-30 2021-10-22 杭州师范大学 一种抗静电、耐摩擦和耐磨损聚甲醛材料及其制备方法
CN110172031A (zh) * 2019-05-23 2019-08-27 北京师范大学 一种阴离子型n-取代苯胺离子液体及其制备方法
CN115650887A (zh) * 2022-10-25 2023-01-31 默尼化工科技(上海)有限公司 一种光学透明耐温长效小分子型抗静电剂及其制备方法和应用
CN115894933A (zh) * 2022-12-07 2023-04-04 世晨材料技术(上海)有限公司 一种有机硅材料用反应型抗静电剂化合物
CN116041708A (zh) * 2022-12-07 2023-05-02 世晨材料技术(上海)有限公司 一种反应型有机硅材料用抗静电剂化合物的制备方法

Similar Documents

Publication Publication Date Title
CN108503550A (zh) 一种离子液体型抗静电剂及其制备方法
CN104829814B (zh) 一种含季铵化哌啶基团的聚合物、制备方法及阴离子交换膜、制备方法
CN104992781B (zh) 一种石墨烯基三元复合材料的制备方法
CN107011371B (zh) 一种含硅咪唑类离子液体及其制备方法和应用
CN106587019B (zh) 一种木质素基生物碳/石墨烯复合纳米材料的制备方法
CN103464123B (zh) Ctmab/cpam/膨润土复合插层材料制备方法
CN108219086B (zh) 一种基于富勒烯阴离子交换膜及其制备方法
CN103817321A (zh) 一种改性纳米银粉的制备方法
CN103035932A (zh) 基于咪唑鎓盐的聚合物阴离子交换膜及其制备方法
CN101994139A (zh) 稀散金属氯化镓/氯化1-甲基-3-丁基咪唑体系电镀液
CN109575464A (zh) 聚噻吩/聚苯乙烯磺酸/碳纳米管复合导电分散液及其制备方法
CN109071570B (zh) 含有硅的硫酸酯盐
CN107737614A (zh) 一种以氢氧化铝作为中间界面层催化剂的双极膜及其制备方法
CN104485470A (zh) 一种聚硅氧烷多膦酸掺杂壳聚糖高温质子交换膜及其制备方法
CN104829813B (zh) 一种含膦离子化聚合物、制备方法及阴离子交换膜
CN103952000B (zh) 钙锌复合稳定剂及其制备方法
CN103785826A (zh) 一种改性纳米镍粉的制备方法
CN107417588A (zh) 一种新型离子液体及采用其电解制备纳米铝的方法
CN103773086B (zh) 一种石墨烯胺功能化组装方法
JP4388776B2 (ja) イオン性液体からなる難燃性溶媒及びその製造方法
CN103585959B (zh) 一种edds改性工程材料及其制备方法
CN104878434B (zh) 一种在铜或铜合金表面制备纳米薄膜的方法
JP6374330B2 (ja) 非水蓄電デバイス用の電解液の製造方法
CN103769580B (zh) 一种改性纳米铁粉的制备方法
CN103387678A (zh) 一种基于peo的凝胶聚合物电解质的制备方法

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20180907