CN1285579C - 新的咪唑醇化合物、其制备方法以及使用该化合物的表面处理剂 - Google Patents
新的咪唑醇化合物、其制备方法以及使用该化合物的表面处理剂 Download PDFInfo
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- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/56—Heterocyclic 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
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Abstract
本发明的目的是提供一种新的咪唑醇化合物，以及使用该化合物的表面处理剂，该化合物能够牢固地吸附在金属特别是铜、铝、钢铁制品的金属表面上，即使是薄膜，也具有优良的防锈作用。下述通式(1)表示的新的咪唑醇化合物显示出防锈作用。(通式(1)中，R1、R2、R3分别表示氢、乙烯基或者碳原子数为1～20的烷基，R2与R3可以形成芳环，X表示氢、碳原子数为1～6的烷基或任选含N、O的取代基，m表示0～20的整数，n、l表示1～3的整数。)上述咪唑醇化合物可以通过使咪唑化合物与环氧醇化合物进行反应而制备。
Description
技术领域
本发明涉及新的咪唑醇化合物，以及以该化合物作为有效成分的表面处理剂。
背景技术
对于各种金属材料表面有各种要求，举例说防止生锈即为其重要特性之一。钢铁制品被用于建筑物、汽车、船只、罐头等各种用途，对其防锈特性有着强烈的要求。为了使钢铁制品具有防锈性能，以前应用水溶性防锈剂、挥发性防锈剂、油性防锈剂等各种防锈剂。通常，水溶性防锈剂用于暂时的短时间防锈目的，而不用于长期防锈。此外，挥发性防锈剂是在密闭状态下发挥其自身防锈功能的物质。油性防锈剂是相对防锈力较强的可发挥长期防锈作用的防锈剂，包括液态防锈油、粘性防锈脂膏、以及将防锈添加剂、薄膜形成剂等溶解于挥发性有机溶剂的防锈剂等。但是，用防锈油或防锈脂膏进行表面处理后产生粘性，不能用作为涂膜等的底层涂料。并且，将防锈添加剂或薄膜形成剂等溶于挥发性有机溶剂的防锈剂若不形成较厚的薄膜则不能发挥充分的防锈效果。
此外，为了抑制铁的生锈，市场上有镀锌钢板销售，这种铁锈的抑制是建立在牺牲比铁离子化倾向更强的锌的防腐性的基础之上的，锌层白锈的防止通过进一步将镀锌层表面进行铬酸盐处理等化学转换处理而实现，从而进一步增强了防腐蚀性。但是虽然这种铬酸盐处理能够使即使很薄的薄膜都具有较高的防锈性能，但是由于环境问题，需要别的防锈薄膜替代这种薄膜。目前，已提出将鞣酸作为镀锌钢板的防锈剂，但现状是与铬酸盐处理相比并不能说其是充分的。
由于质轻，铝或铝合金在各种领域均倍受关注。然而，由于表面上形成氧化铝薄膜，即使对铝直接涂布涂料，其附着性也不充分。现已提出了许多涂布底层用的化学转化方法，如今也申请了很多专利，但目前在美国和日本铬酸盐处理仍然是主流。然而，与上述镀锌钢板同样，在环境方面铬酸盐处理并不是理想的方法，需要非铬酸盐处理方法。此外，为了使金属表面具有防腐性和抗静电性等性能，还提出了用硅酸碱金属盐水溶液进行处理的方法，但其处理温度高，并需要进行沸水浸渍或酸浸渍作为后处理，如果不除去碱金属则得不到所需的特性。
发明的公开
本发明的目的是提供一种新的咪唑醇化合物，以及使用该化合物的表面处理剂，该化合物能够满足上述要求，即能够牢固地吸附在金属特别是铜、铝、钢铁制品的金属表面上，即使是薄膜，也具有优良的防锈作用。
本发明者们进行了深入的研究，结果发现下述式(1)表示的新的咪唑醇化合物对金属表面具有优良的防锈作用。
本发明是基于这种认识而作出的，其要点如以下(1)～(3)项：
(1)下述通式(1)表示的新的咪唑醇化合物。
(通式(1)中，R1、R2、R3分别表示氢、乙烯基或者碳原子数为1～20的烷基，R2与R3可以形成芳环，X表示氢、碳原子数为1～6的烷基或任选含N、O的取代基，m表示0～20的整数，n、l表示1～3的整数。)
(2)上述(1)所述的咪唑醇化合物的制备方法，其特征在于使下述通式(2)表示的咪唑化合物与下述通式(3)表示的环氧醇化合物进行反应。
(通式(2)中，R1、R2、R3分别表示氢、乙烯基或者碳原子数为1～20的烷基，R2与R3可以形成芳环，通式(3)中，X表示氢、碳原子数为1～6的烷基或任选含N、O的取代基，m表示0～20的整数，n、l表示1～3的整数。)
(3)以上述(1)所述的咪唑醇化合物作为有效成分的表面处理剂。
以下对本发明进行更详细的说明。
上述通式(1)～(3)中，当R1、R2、R3为氢、乙烯基或者碳原子数为1～20的烷基时，能够充分发挥本发明的效果。作为烷基，优选碳原子数为1～20。此外，当R2与R3形成芳环时，所形成的芳环优选为苯环。X为氢、碳原子数为1～6的烷基或任选含N、O的取代基，作为碳原子数为1～6的烷基，优选碳原子数为1～4的烷基，作为含N、O的取代基，可以列举羟基、羧基、氨基等。
本发明的上述咪唑醇化合物(1)通过下述反应式(4)表示的反应式合成。即可以通过将咪唑化合物与环氧醇化合物混合，并加热至80～200℃而制备。
(式中，R1、R2、R3、X、l、m以及n与上述定义相同。)
作为上述通式(2)表示的咪唑化合物，优选咪唑、2-烷基咪唑、2，4-二烷基咪唑、4-乙烯基咪唑等。其中特别优选咪唑；作为2-烷基咪唑，可以列举2-甲基咪唑、2-乙基咪唑、2-十一烷基咪唑；以及，作为2，4-二烷基咪唑，可以列举2-乙基-4-甲基咪唑等。
作为上述通式(3)表示环氧醇化合物，优选环氧丙醇、环氧丁醇、环氧戊醇、环氧己醇等，特别优选环氧丙醇。
上述咪唑化合物与环氧醇化合物的反应通过向加热至80～200℃的咪唑化合物中滴加0.1～10摩尔倍数的环氧醇化合物而进行比较适宜，反应时间为5分钟～2小时即足够。该反应并不一定需要溶剂，但也可以用氯仿、二烷、甲醇、乙醇等有机溶剂作为反应溶剂。此外，由于该反应厌水，为防止水份混入，优选在干燥氮气、氩气等不含水份的气体氛围下进行。
本发明上述通式(1)表示的化合物也可以用作化学机械研磨(chemicalmechanical polishing)添加剂、润湿性加工剂，但作为防锈剂特别有用。当本发明的咪唑醇化合物作为表面处理剂用于金属时，通常优选用溶剂稀释后使用。此时，还可以添加溶剂可溶性树脂(环氧树脂、丙烯酸树脂等)、硅烷偶合剂以及粘度调节剂、消泡剂、紫外线吸收剂、防腐剂、表面活性剂等。
当本发明的咪唑醇化合物用作表面处理剂时，溶剂可以使用水系溶剂或者溶剂类溶剂。作为溶剂类溶剂，有甲醇、乙醇、异丙醇、甲苯、醋酸乙酯等。
本发明的表面处理剂适用于金属，特别是对铜和铜合金具有特别优良的防锈作用。作为将本发明的表面处理剂涂布在金属表面的方法，可以应用喷涂法、浸涂法、刷涂法、辊涂法等公知的涂布方法。
为了充分发挥本发明的表面处理剂的效果，优选涂布后进行加热干燥。加热干燥优选在100～230℃下干燥30秒～60分钟。涂布后在加热的条件下，通过除去水分能够提高对金属的附着性，从而增强了防锈性能。优选干燥后涂膜的厚度为0.01～100μm。更优选为0.05～10μm。当不足0.01μm时，不能获得足够的防锈性能，而当超过100μm时，不能得到均匀的涂膜。
附图的简单说明
图1为实施例1中所得本发明新的咪唑醇化合物的1H-NMR光谱。
图2为实施例2的俄歇分析结果。
图3为比较例1的俄歇分析结果。
实施发明的最佳方式
以下通过实施例对本发明进行具体的说明。
实施例1
咪唑醇化合物的合成
将9.2g咪唑加热至120℃，滴加10g 2，3-环氧丙醇，然后在150℃下使其反应3小时，得到19g下述式(5)表示的目标产物。所得化合物通过NMR测定进行鉴定。本化合物的1H-NMR光谱见图1。
实施例2
作为表面处理剂的应用
将实施例1中制得的咪唑醇化合物(5)的10％水溶液(pH 11.5)涂布于铜箔上，在150℃下加热处理30分钟。然后，进行俄歇分析。结果见图2。如图2所示，氧的检测量很低，并且可知在高pH下显示高的防锈效果。
比较例1
除了不在铜箔上涂布本发明化合物以外，与实施例同样地操作，并同样地进行俄歇分析。结果见图3。
产业上的可利用性
含有本发明的咪唑醇化合物的组合物显示出优良的防锈性能。
Claims (3)
1、下述通式(1)表示的新的咪唑醇化合物，
通式(1)中，R1表示氢或或者碳原子数为1～20的烷基，R2表示氢、乙烯基或者碳原子数为1～20的烷基，R3表示氢，X表示氢，m表示0～3的整数，n、l表示1。
2、如权利要求1所述的咪唑醇化合物的制备方法，其特征在于，使下述通式(2)表示的咪唑化合物与下述通式(3)表示的环氧醇化合物进行反应，
通式(2)中，R1表示氢或者碳原子数为1～20的烷基，R2表示氢、乙烯基或者碳原子数为1～20的烷基，R3表示氢，通式(3)中，X表示氢，m表示0～3的整数，n、l表示1。
3、以权利要求1所述的咪唑醇化合物作为有效成分的金属表面处理剂。
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| JP2002219716A JP4183999B2 (ja) | 2002-07-29 | 2002-07-29 | イミダゾールアルコールを有効成分とする表面処理剤 |
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| JP (1) | JP4183999B2 (zh) |
| KR (1) | KR100629039B1 (zh) |
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| CN106687447A (zh) * | 2014-08-29 | 2017-05-17 | 东京应化工业株式会社 | 咪唑化合物、金属表面处理液、金属的表面处理方法、及层合体的制造方法 |
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| CN101087738B (zh) * | 2004-12-23 | 2010-11-10 | 贝卡尔特股份有限公司 | 包括水泥基质和镀锌金属元件的增强结构 |
| US8268157B2 (en) * | 2010-03-15 | 2012-09-18 | Rohm And Haas Electronic Materials Llc | Plating bath and method |
| US8262895B2 (en) * | 2010-03-15 | 2012-09-11 | Rohm And Haas Electronic Materials Llc | Plating bath and method |
| US20110220512A1 (en) * | 2010-03-15 | 2011-09-15 | Rohm And Haas Electronic Materials Llc | Plating bath and method |
| CN105732527B (zh) * | 2016-02-02 | 2018-03-06 | 陕西科技大学 | 一种三氮唑改性曼尼希碱化合物及其制备方法 |
| US10023540B2 (en) * | 2016-09-29 | 2018-07-17 | Tokyo Ohka Kogyo Co., Ltd. | Hydrogen barrier agent, hydrogen barrier film forming composition, hydrogen barrier film, method for producing hydrogen barrier film, and electronic element |
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| DE3175673D1 (en) * | 1980-11-19 | 1987-01-15 | Ici Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| EP0061835B1 (en) * | 1981-03-18 | 1989-02-01 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| JPS60181076A (ja) | 1984-02-27 | 1985-09-14 | Shikoku Chem Corp | ２‐ビニル‐４，６‐ジアミノ‐ｓ‐トリアジンの合成方法 |
| US5698391A (en) * | 1991-08-23 | 1997-12-16 | Isis Pharmaceuticals, Inc. | Methods for synthetic unrandomization of oligomer fragments |
| JP3171986B2 (ja) * | 1992-09-22 | 2001-06-04 | 株式会社ジャパンエナジー | 新規イミダゾールフッ素誘導体及びその製造方法並びにそれを用いる表面処理剤 |
| US5886177A (en) * | 1994-01-11 | 1999-03-23 | Isis Pharmaceuticals, Inc. | Phosphate linked oligomers |
| US6448373B1 (en) | 1994-01-11 | 2002-09-10 | Isis Pharmaceuticals, Inc. | Phosphate linked oligomers formed of monomeric diols and processes for preparing same |
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| CN106687447A (zh) * | 2014-08-29 | 2017-05-17 | 东京应化工业株式会社 | 咪唑化合物、金属表面处理液、金属的表面处理方法、及层合体的制造方法 |
| CN106687447B (zh) * | 2014-08-29 | 2020-06-02 | 东京应化工业株式会社 | 咪唑化合物、金属表面处理液、金属的表面处理方法、及层合体的制造方法 |
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| KR20050016998A (ko) | 2005-02-21 |
| JP4183999B2 (ja) | 2008-11-19 |
| US20060135584A1 (en) | 2006-06-22 |
| JP2004059497A (ja) | 2004-02-26 |
| TWI333000B (en) | 2010-11-11 |
| TW200401769A (en) | 2004-02-01 |
| WO2004011437A1 (ja) | 2004-02-05 |
| CN1671670A (zh) | 2005-09-21 |
| US7968150B2 (en) | 2011-06-28 |
| US20090068364A1 (en) | 2009-03-12 |
| KR100629039B1 (ko) | 2006-09-26 |
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