WO2021208602A1 - Benzotriazole derivative corrosion inhibitor, preparation method therefor and use thereof - Google Patents
Benzotriazole derivative corrosion inhibitor, preparation method therefor and use thereof Download PDFInfo
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- WO2021208602A1 WO2021208602A1 PCT/CN2021/077714 CN2021077714W WO2021208602A1 WO 2021208602 A1 WO2021208602 A1 WO 2021208602A1 CN 2021077714 W CN2021077714 W CN 2021077714W WO 2021208602 A1 WO2021208602 A1 WO 2021208602A1
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- corrosion inhibitor
- benzotriazole
- benzotriazole derivative
- formaldehyde
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- 238000005260 corrosion Methods 0.000 title claims abstract description 80
- 230000007797 corrosion Effects 0.000 title claims abstract description 78
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 title claims abstract description 73
- 239000003112 inhibitor Substances 0.000 title claims abstract description 70
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 96
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000012964 benzotriazole Substances 0.000 claims abstract description 23
- 239000002994 raw material Substances 0.000 claims abstract description 23
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052802 copper Inorganic materials 0.000 claims abstract description 17
- 239000010949 copper Substances 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 10
- 239000008098 formaldehyde solution Substances 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 abstract description 5
- 238000009776 industrial production Methods 0.000 abstract description 4
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 230000033228 biological regulation Effects 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004395 organic heterocyclic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- 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
- C23F11/14—Nitrogen-containing compounds
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
Definitions
- the invention relates to the technical field of chemical reagents, in particular to a corrosion inhibitor of benzotriazole derivatives, and a preparation method and application thereof.
- Corrosion of metal equipment and workpieces has always been a serious problem faced by various production and processing enterprises. It will not only cause serious capital losses, increase production costs and decrease production efficiency, but also cause a certain waste of resources. Because of its good processing properties, mechanical strength, thermal conductivity, electrical conductivity, and corrosion resistance, copper is widely used in various processing and manufacturing enterprises and the electronics industry. One aspect that must be considered for a large number of application fields and uses is the corrosion protection of copper. Although metallic copper has good corrosion resistance, in some special application environments, such as oxygen-containing water, acidic solutions, and aqueous solutions containing CN - or NH 4+ ions, it will cause severe corrosion to copper.
- copper corrosion inhibitors used in China are thiourea, aldehyde, aniline, amine derivatives and thiazole and other organic heterocyclic compounds, such as benzotriazole in a relatively large amount.
- benzotriazole generally cannot be used alone because of its poor water solubility. It needs to be neutralized with organic amines or inorganic bases to greatly reduce its convenience.
- the prepared benzotriazole derivative corrosion inhibitor has excellent hydrophilicity and can reach the traditional level.
- a preparation method of benzotriazole derivative corrosion inhibitor includes the following steps:
- the temperature is raised to 85°C to 110°C, and then the temperature is kept for a predetermined time for reaction;
- the temperature was lowered to room temperature to obtain the product.
- the prepared benzotriazole derivative copper corrosion inhibitor has excellent hydrophilicity and can be used directly without first being converted into a water-soluble salt and then used to inhibit corrosion
- the performance is good, and it is not restricted by the EU REACH specification; in addition, the preparation method of the benzotriazole derivative corrosion inhibitor of the present invention is simple and easy to be applied in industrial production.
- the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1-1.5:1:1-1.5.
- the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1.4-1.5:1:1.2-1.5.
- the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1.5:1:1.3-1.5.
- the formaldehyde is a formaldehyde solution of 37 wt% to 40 wt%.
- the incubation reaction time is 3-10 hours.
- the present invention also provides a benzotriazole derivative corrosion inhibitor prepared by the preparation method of any one of the above-mentioned benzotriazole derivative corrosion inhibitors, which has excellent hydrophilicity and can be used directly It does not need to be converted into water-soluble salt before use, and has good corrosion inhibition performance.
- the structure of the benzotriazole derivative is:
- the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 85%-95%.
- the benzotriazole derivative corrosion inhibitor described in any one of the above can be used as a copper corrosion inhibitor and has a good anti-corrosion effect.
- Figure 1 is a comparison diagram of the test results of the benzotriazole derivative corrosion inhibitor of Example 5 and the comparative example.
- the invention provides a preparation method of a benzotriazole derivative corrosion inhibitor, which comprises the following steps:
- the molar ratio of benzotriazole, diethanolamine, and formaldehyde is 1-1.5:1:1-1.5.
- the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1.4-1.5:1:1.2-1.5, the yield of the benzotriazole derivative is higher, and the reaction efficiency is faster.
- the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1.5:1:1.3 ⁇ 1.5, the yield of benzotriazole derivatives is higher, the reaction efficiency is faster, and it can be diluted with water when used. A wide range of concentrations makes the application more flexible.
- the formaldehyde is a formaldehyde solution of 37 wt% to 40 wt%.
- Benzotriazole, diethanolamine is a formaldehyde solution of 37 wt% to 40 wt%.
- the present invention also provides a benzotriazole derivative corrosion inhibitor prepared by adopting the preparation method of the benzotriazole derivative corrosion inhibitor.
- the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 85%-95%.
- the above-mentioned benzotriazole derivative corrosion inhibitor can be used as a copper corrosion inhibitor, or other metal corrosion inhibitor, and copper has the best corrosion inhibitor effect.
- the prepared benzotriazole derivative copper corrosion inhibitor has excellent hydrophilicity and can be used directly without being converted into a water-soluble salt. Good corrosion performance.
- the preparation method of the benzotriazole derivative corrosion inhibitor of the present invention can also survive the condensation reaction without adding other raw materials, and the effective ingredient benzotriazole derivative has a high production rate. After the production is completed, the product can be taken directly and used without first being converted into a water-soluble salt. The resulting product is not restricted by the EU REACH regulations, which reduces the generation and treatment procedures of impurities, and is simple to operate and easy to apply in industrial production.
- the formaldehyde is 37wt%-40wt% formaldehyde solution.
- the formaldehyde is 37wt%-40wt% formaldehyde solution.
- the formaldehyde is 37wt%-40wt% formaldehyde solution.
- the formaldehyde is 37wt%-40wt% formaldehyde solution.
- the formaldehyde is 37wt%-40wt% formaldehyde solution.
- the formaldehyde is 37wt%-40wt% formaldehyde solution.
- Reagent preparation Add the benzotriazole derivative corrosion inhibitor of Example 1 to water to make the mass fraction of the benzotriazole derivative corrosion inhibitor 0.1%, then add 100 ppm active sulfur, and use monoethanolamine to adjust the pH When the value reaches 9.5-10, the experimental reagent of Example 1 is obtained.
- the experimental reagents of Examples 1 to 6 and the experimental reagents of the commercially available rust inhibitor T706 were respectively tested for copper corrosion according to GB6144-2010, and were compared with the blank sample. The blank sample was made without any anti-corrosion on the copper sample.
- the test results are as follows Table 1.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
The present invention provides a benzotriazole derivative corrosion inhibitor, a preparation method therefor and the use thereof. The preparation method comprises the following steps: placing benzotriazole, diethanolamine and formaldehyde in a reaction vessel, and mixing same to obtain a mixed raw material; raising the temperature to 85-110ºC while stirring the mixed raw material, and then maintaining the temperature and reacting same for a pre-set time; and cooling same to room temperature to obtain a product. The prepared benzotriazole derivative copper corrosion inhibitor has excellent hydrophilicity, can be directly used without being converted to a water-soluble salt before use, has good corrosion inhibition and can be used without being limited by European Union REACH regulations. Furthermore, the preparation method for the benzotriazole derivative corrosion inhibitor of the present invention is simple, and easily applied in industrial production.
Description
本发明涉及化学试剂技术领域，特别是涉及苯并三氮唑衍生物缓蚀剂及其制备方法与应用。The invention relates to the technical field of chemical reagents, in particular to a corrosion inhibitor of benzotriazole derivatives, and a preparation method and application thereof.
金属设备以及工件的腐蚀一直是目前各类生产加工型企业面临的严重问题，不仅会造成企业在资金上严重损失、生产成本上增加和生产效率上降低，而且还会造成一定的资源浪费。铜因其具有良好的加工性能、机械强度、导热性、导电性以及耐腐蚀等特点，广泛应用于各类加工制造企业和电子工业等领域。大量的应用领域和使用数量，必定要考虑的一个方面，也就是铜的抗腐蚀保护。虽然金属铜具有较好的耐腐蚀性能，但是在一些特殊的应用环境中，比如含氧的水、酸性溶液、含有CN
-或NH
4+离子的水溶液等环境，都会对铜造成严重的腐蚀。因此，为了有效抑制铜腐蚀的发生，目前采用较多的方式就是使用铜缓蚀剂。国内使用较多的铜缓蚀剂类型主要有硫脲、醛、苯胺、胺的衍生物和噻唑等有机杂环化合物，如用量比较大的苯并三氮唑。但是苯并三氮唑因为水溶性较差一般不能单独使用，需要和有机胺或者无机碱中和后使用使其方便性大大下降。
Corrosion of metal equipment and workpieces has always been a serious problem faced by various production and processing enterprises. It will not only cause serious capital losses, increase production costs and decrease production efficiency, but also cause a certain waste of resources. Because of its good processing properties, mechanical strength, thermal conductivity, electrical conductivity, and corrosion resistance, copper is widely used in various processing and manufacturing enterprises and the electronics industry. One aspect that must be considered for a large number of application fields and uses is the corrosion protection of copper. Although metallic copper has good corrosion resistance, in some special application environments, such as oxygen-containing water, acidic solutions, and aqueous solutions containing CN - or NH 4+ ions, it will cause severe corrosion to copper. Therefore, in order to effectively inhibit the occurrence of copper corrosion, a more common method is to use copper corrosion inhibitors. The main types of copper corrosion inhibitors used in China are thiourea, aldehyde, aniline, amine derivatives and thiazole and other organic heterocyclic compounds, such as benzotriazole in a relatively large amount. However, benzotriazole generally cannot be used alone because of its poor water solubility. It needs to be neutralized with organic amines or inorganic bases to greatly reduce its convenience.
发明内容Summary of the invention
基于此，有必要针对上述问题，提供一种苯并三氮唑衍生物缓蚀剂的制备方法，其制备的苯并三氮唑衍生物缓蚀剂具有优良的亲水性，且可以达到传统 的同等的铜缓蚀效果，制备方法简单，易于应用在工业生产。Based on this, it is necessary to address the above problems and provide a method for preparing a benzotriazole derivative corrosion inhibitor. The prepared benzotriazole derivative corrosion inhibitor has excellent hydrophilicity and can reach the traditional level. The same copper corrosion inhibition effect, simple preparation method, easy to apply in industrial production.
一种苯并三氮唑衍生物缓蚀剂的制备方法，包括以下步骤：A preparation method of benzotriazole derivative corrosion inhibitor includes the following steps:
将苯并三氮唑、二乙醇胺和甲醛置于在反应容器中进行混合，获得混合原料；Put benzotriazole, diethanolamine and formaldehyde in a reaction vessel for mixing to obtain mixed raw materials;
边搅拌所述混合原料边升温至85℃～110℃，然后保温反应预设时间；While stirring the mixed raw materials, the temperature is raised to 85°C to 110°C, and then the temperature is kept for a predetermined time for reaction;
降温至室温，获得产品。The temperature was lowered to room temperature to obtain the product.
上述苯并三氮唑衍生物缓蚀剂的制备方法，制备的苯并三氮唑衍生物类的铜缓蚀剂具有优良亲水性可以直接使用不用先转换成水溶性盐再使用，缓腐蚀性能良好，且不受欧盟REACH规范所限制使用；另外，本发明的苯并三氮唑衍生物缓蚀剂的制备方法简单，易于应用在工业生产。The method for preparing the above-mentioned benzotriazole derivative corrosion inhibitor, the prepared benzotriazole derivative copper corrosion inhibitor has excellent hydrophilicity and can be used directly without first being converted into a water-soluble salt and then used to inhibit corrosion The performance is good, and it is not restricted by the EU REACH specification; in addition, the preparation method of the benzotriazole derivative corrosion inhibitor of the present invention is simple and easy to be applied in industrial production.
在其中一个实施例中，苯并三氮唑、二乙醇胺和甲醛的摩尔比为1～1.5：1：1～1.5。In one of the embodiments, the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1-1.5:1:1-1.5.
在其中一个实施例中，苯并三氮唑、二乙醇胺和甲醛的摩尔比为1.4～1.5：1：1.2～1.5。In one of the embodiments, the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1.4-1.5:1:1.2-1.5.
在其中一个实施例中，苯并三氮唑、二乙醇胺和甲醛的摩尔比为1.5：1：1.3～1.5。In one of the embodiments, the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1.5:1:1.3-1.5.
在其中一个实施例中，甲醛为37wt％～40wt％的甲醛溶液。In one of the embodiments, the formaldehyde is a formaldehyde solution of 37 wt% to 40 wt%.
在其中一个实施例中，保温反应时间为3～10小时。In one of the embodiments, the incubation reaction time is 3-10 hours.
本发明还提供了一种采用上述任一项所述的苯并三氮唑衍生物缓蚀剂的制备方法制成的苯并三氮唑衍生物缓蚀剂，具有优良亲水性可以直接使用不用先转换成水溶性盐再使用，缓腐蚀性能良好。The present invention also provides a benzotriazole derivative corrosion inhibitor prepared by the preparation method of any one of the above-mentioned benzotriazole derivative corrosion inhibitors, which has excellent hydrophilicity and can be used directly It does not need to be converted into water-soluble salt before use, and has good corrosion inhibition performance.
在其中一个实施例中，苯并三氮唑衍生物的结构为：In one of the embodiments, the structure of the benzotriazole derivative is:
[援引加入(细则20.6) 28.05.2021]
。[Added by reference (Rule 20.6) 28.05.2021]
.
在其中一个实施例中，苯并三氮唑衍生物于所述苯并三氮唑衍生物缓蚀剂中的质量含量为85％～95％。In one of the embodiments, the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 85%-95%.
上述任一项所述的苯并三氮唑衍生物缓蚀剂可以应用作为铜缓蚀剂，防腐蚀效果佳。The benzotriazole derivative corrosion inhibitor described in any one of the above can be used as a copper corrosion inhibitor and has a good anti-corrosion effect.
图1为实施例5的苯并三氮唑衍生物缓蚀剂与对比例的试验结果对照图。Figure 1 is a comparison diagram of the test results of the benzotriazole derivative corrosion inhibitor of Example 5 and the comparative example.
为了便于理解本发明，下面将对本发明进行更全面的描述。但是，本发明可以以许多不同的形式来实现，并不限于本文所描述的实施例。相反地，提供这些实施例的目的是使对本发明的公开内容的理解更加透彻全面。In order to facilitate the understanding of the present invention, the present invention will be described more fully below. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosure of the present invention more thorough and comprehensive.
除非另有定义，本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施例的目的，不是旨在于限制本发明。Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the technical field of the present invention. The terms used in the specification of the present invention herein are only for the purpose of describing specific embodiments, and are not intended to limit the present invention.
本发明提供了一种苯并三氮唑衍生物缓蚀剂的制备方法，包括以下步骤：The invention provides a preparation method of a benzotriazole derivative corrosion inhibitor, which comprises the following steps:
S100：将苯并三氮唑、二乙醇胺和甲醛置于在反应容器中进行混合，获得 混合原料。S100: Put benzotriazole, diethanolamine and formaldehyde in a reaction vessel and mix to obtain mixed raw materials.
一个实施例中，苯并三氮唑、二乙醇胺和甲醛的摩尔比为1～1.5：1：1～1.5。较优地，苯并三氮唑、二乙醇胺和甲醛的摩尔比为1.4～1.5：1：1.2～1.5，苯并三氮唑衍生物的产率较高，反应效率较快。最优地，苯并三氮唑、二乙醇胺和甲醛的摩尔比为1.5：1：1.3～1.5，苯并三氮唑衍生物的产率较高，反应效率较快，使用时可以用水稀释更大范围的浓度，应用更灵活。In an embodiment, the molar ratio of benzotriazole, diethanolamine, and formaldehyde is 1-1.5:1:1-1.5. Preferably, the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1.4-1.5:1:1.2-1.5, the yield of the benzotriazole derivative is higher, and the reaction efficiency is faster. Optimally, the molar ratio of benzotriazole, diethanolamine and formaldehyde is 1.5:1:1.3～1.5, the yield of benzotriazole derivatives is higher, the reaction efficiency is faster, and it can be diluted with water when used. A wide range of concentrations makes the application more flexible.
一个实施例中，甲醛为37wt％～40wt％的甲醛溶液。苯并三氮唑、二乙醇胺In one embodiment, the formaldehyde is a formaldehyde solution of 37 wt% to 40 wt%. Benzotriazole, diethanolamine
S200：边搅拌所述混合原料边升温至85℃～110℃，然后保温反应预设时间。较优地，保温反应时间为3～10小时，使混合原料可以充分反应。反应过程采用常压回流的方式，使原料可以长时间反应。S200: While stirring the mixed raw materials, the temperature is raised to 85°C to 110°C, and then the temperature is kept and reacted for a preset time. Preferably, the heat preservation reaction time is 3-10 hours, so that the mixed raw materials can fully react. The reaction process adopts normal pressure reflux, so that the raw materials can react for a long time.
苯并三氮唑、二乙醇胺和甲醛在此步骤中进行缩合反应，反应方程式如下：Benzotriazole, diethanolamine and formaldehyde undergo condensation reaction in this step, and the reaction equation is as follows:
[援引加入(细则20.6) 28.05.2021]
。[Added by reference (Rule 20.6) 28.05.2021]
.
苯并三氮唑衍生物的结构为：The structure of benzotriazole derivatives is:
[援引加入(细则20.6) 28.05.2021]
。[Added by reference (Rule 20.6) 28.05.2021]
.
S300：降温至室温，获得产品。S300: Cool down to room temperature to obtain the product.
本发明还提供了一种采用上述苯并三氮唑衍生物缓蚀剂的制备方法制成的苯并三氮唑衍生物缓蚀剂。The present invention also provides a benzotriazole derivative corrosion inhibitor prepared by adopting the preparation method of the benzotriazole derivative corrosion inhibitor.
在其中一个实施例中，苯并三氮唑衍生物于苯并三氮唑衍生物缓蚀剂中的质量含量为85％～95％。In one of the embodiments, the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 85%-95%.
上述苯并三氮唑衍生物缓蚀剂可应用作为铜缓蚀剂，或者其他金属的缓蚀剂，铜的缓蚀效果最佳。The above-mentioned benzotriazole derivative corrosion inhibitor can be used as a copper corrosion inhibitor, or other metal corrosion inhibitor, and copper has the best corrosion inhibitor effect.
本发明苯并三氮唑衍生物缓蚀剂的制备方法，制备的苯并三氮唑衍生物类的铜缓蚀剂具有优良亲水性可以直接使用不用先转换成水溶性盐再使用，缓腐蚀性能良好。而且，本发明的苯并三氮唑衍生物缓蚀剂的制备方法在不加入其他原料的情况下也能活得良好的缩合反应结果，有效成分苯并三氮唑衍生物的生成率高，生产完成后可直接取产品使用，不用先转换成水溶性盐，生成的产物不受欧盟REACH规范所限制使用，减少了杂质的产生和处理工序，操作简单，易于应用在工业生产。In the preparation method of the benzotriazole derivative corrosion inhibitor of the present invention, the prepared benzotriazole derivative copper corrosion inhibitor has excellent hydrophilicity and can be used directly without being converted into a water-soluble salt. Good corrosion performance. Moreover, the preparation method of the benzotriazole derivative corrosion inhibitor of the present invention can also survive the condensation reaction without adding other raw materials, and the effective ingredient benzotriazole derivative has a high production rate. After the production is completed, the product can be taken directly and used without first being converted into a water-soluble salt. The resulting product is not restricted by the EU REACH regulations, which reduces the generation and treatment procedures of impurities, and is simple to operate and easy to apply in industrial production.
以下为具体实施例说明。The following is a description of specific embodiments.
实施例1Example 1
本实施例的苯并三氮唑衍生物缓蚀剂的制备方法，包括以下步骤：The preparation method of the benzotriazole derivative corrosion inhibitor of this embodiment includes the following steps:
S100：将摩尔比为1：1：1的苯并三氮唑、二乙醇胺和甲醛置于在反应容器中进行混合，获得混合原料。S100: Put benzotriazole, diethanolamine, and formaldehyde in a reaction vessel with a molar ratio of 1:1:1 to mix to obtain mixed raw materials.
甲醛为37wt％～40wt％的甲醛溶液。The formaldehyde is 37wt%-40wt% formaldehyde solution.
S200：边搅拌所述混合原料边升温至90℃，然后保温反应4小时。S200: While stirring the mixed raw materials, the temperature is raised to 90°C, and then the temperature is kept and reacted for 4 hours.
S300：降温至室温，获得产品苯并三氮唑衍生物缓蚀剂，苯并三氮唑衍生物于苯并三氮唑衍生物缓蚀剂中的质量含量为88％。S300: Cool down to room temperature to obtain the product benzotriazole derivative corrosion inhibitor, and the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 88%.
实施例2Example 2
本实施例的苯并三氮唑衍生物缓蚀剂的制备方法，包括以下步骤：The preparation method of the benzotriazole derivative corrosion inhibitor of this embodiment includes the following steps:
S100：将摩尔比为1.2：1：1.4的苯并三氮唑、二乙醇胺和甲醛置于在反应容器中进行混合，获得混合原料。S100: Put benzotriazole, diethanolamine, and formaldehyde in a reaction vessel with a molar ratio of 1.2:1:1.4 to mix to obtain mixed raw materials.
甲醛为37wt％～40wt％的甲醛溶液。The formaldehyde is 37wt%-40wt% formaldehyde solution.
S200：边搅拌所述混合原料边升温至86℃，然后保温反应8小时。S200: While stirring the mixed raw materials, the temperature is raised to 86°C, and then the temperature is kept and reacted for 8 hours.
S300：降温至室温，获得产品苯并三氮唑衍生物缓蚀剂，苯并三氮唑衍生物于苯并三氮唑衍生物缓蚀剂中的质量含量为87％。S300: Cool down to room temperature to obtain the product benzotriazole derivative corrosion inhibitor, and the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 87%.
实施例3Example 3
本实施例的苯并三氮唑衍生物缓蚀剂的制备方法，包括以下步骤：The preparation method of the benzotriazole derivative corrosion inhibitor of this embodiment includes the following steps:
S100：将摩尔比为1.4：1：1.3的苯并三氮唑、二乙醇胺和甲醛置于在反应容器中进行混合，获得混合原料。S100: Put benzotriazole, diethanolamine, and formaldehyde in a reaction vessel with a molar ratio of 1.4:1:1.3 to mix to obtain mixed raw materials.
甲醛为37wt％～40wt％的甲醛溶液。The formaldehyde is 37wt%-40wt% formaldehyde solution.
S200：边搅拌所述混合原料边升温至95℃，然后保温反应10小时。S200: While stirring the mixed raw materials, the temperature is raised to 95°C, and then the temperature is kept and reacted for 10 hours.
S300：降温至室温，获得产品苯并三氮唑衍生物缓蚀剂，苯并三氮唑衍生物于苯并三氮唑衍生物缓蚀剂中的质量含量为93％。S300: Cool down to room temperature to obtain the product benzotriazole derivative corrosion inhibitor, and the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 93%.
实施例4Example 4
本实施例的苯并三氮唑衍生物缓蚀剂的制备方法，包括以下步骤：The preparation method of the benzotriazole derivative corrosion inhibitor of this embodiment includes the following steps:
S100：将摩尔比为1～1.5：1：1.4的苯并三氮唑、二乙醇胺和甲醛置于在反应容器中进行混合，获得混合原料。S100: Put benzotriazole, diethanolamine, and formaldehyde in a reaction vessel with a molar ratio of 1 to 1.5:1:1.4 to mix to obtain mixed raw materials.
甲醛为37wt％～40wt％的甲醛溶液。The formaldehyde is 37wt%-40wt% formaldehyde solution.
S200：边搅拌所述混合原料边升温至105℃，然后保温反应7小时。S200: While stirring the mixed raw materials, the temperature is raised to 105°C, and then the temperature is kept and reacted for 7 hours.
S300：降温至室温，获得产品苯并三氮唑衍生物缓蚀剂，苯并三氮唑衍生物于苯并三氮唑衍生物缓蚀剂中的质量含量为94％。S300: Cool down to room temperature to obtain the product benzotriazole derivative corrosion inhibitor, and the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 94%.
实施例5Example 5
本实施例的苯并三氮唑衍生物缓蚀剂的制备方法，包括以下步骤：The preparation method of the benzotriazole derivative corrosion inhibitor of this embodiment includes the following steps:
S100：将摩尔比为1.5：1：1.5的苯并三氮唑、二乙醇胺和甲醛置于在反应容器中进行混合，获得混合原料。S100: Put benzotriazole, diethanolamine, and formaldehyde in a reaction vessel with a molar ratio of 1.5:1:1.5 to mix to obtain mixed raw materials.
甲醛为37wt％～40wt％的甲醛溶液。The formaldehyde is 37wt%-40wt% formaldehyde solution.
S200：边搅拌所述混合原料边升温至85℃～110℃，然后保温反应3～10小时。S200: While stirring the mixed raw materials, the temperature is raised to 85°C to 110°C, and then the temperature is kept and reacted for 3 to 10 hours.
S300：降温至室温，获得产品苯并三氮唑衍生物缓蚀剂，苯并三氮唑衍生物于苯并三氮唑衍生物缓蚀剂中的质量含量为91％。S300: Cool down to room temperature to obtain the product benzotriazole derivative corrosion inhibitor, and the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 91%.
实施例6Example 6
本实施例的苯并三氮唑衍生物缓蚀剂的制备方法，包括以下步骤：The preparation method of the benzotriazole derivative corrosion inhibitor of this embodiment includes the following steps:
S100：将摩尔比为1.5：1：1.3的苯并三氮唑、二乙醇胺和甲醛置于在反应容器中进行混合，获得混合原料。S100: Put benzotriazole, diethanolamine, and formaldehyde in a reaction vessel with a molar ratio of 1.5:1:1.3 to mix to obtain mixed raw materials.
甲醛为37wt％～40wt％的甲醛溶液。The formaldehyde is 37wt%-40wt% formaldehyde solution.
S200：边搅拌所述混合原料边升温至110℃，然后保温反应5小时。S200: While stirring the mixed raw materials, the temperature is raised to 110°C, and then the temperature is kept and reacted for 5 hours.
S300：降温至室温，获得产品苯并三氮唑衍生物缓蚀剂，苯并三氮唑衍生 物于苯并三氮唑衍生物缓蚀剂中的质量含量为90％。S300: Cool down to room temperature to obtain the product benzotriazole derivative corrosion inhibitor, and the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is 90%.
应用试验Application test
将实施例1至6的苯并三氮唑衍生物缓蚀剂与市售防锈剂T706做对比试验。The benzotriazole derivative corrosion inhibitors of Examples 1 to 6 were compared with the commercially available rust inhibitor T706.
准备试剂：将实施例1的苯并三氮唑衍生物缓蚀剂加入水，使苯并三氮唑衍生物缓蚀剂的质量分数为0.1％，再加入100ppm活性硫，采用单乙醇胺调节PH值至9.5～10，获得实施例1的实验试剂。Reagent preparation: Add the benzotriazole derivative corrosion inhibitor of Example 1 to water to make the mass fraction of the benzotriazole derivative corrosion inhibitor 0.1%, then add 100 ppm active sulfur, and use monoethanolamine to adjust the pH When the value reaches 9.5-10, the experimental reagent of Example 1 is obtained.
实施例2至6的实验试剂及市售防锈剂T706的实验试剂均采用相同的方法制备。The experimental reagents of Examples 2 to 6 and the experimental reagents of the commercially available rust inhibitor T706 were prepared by the same method.
实施例1至6的实验试剂及市售防锈剂T706的实验试剂分别按照GB6144-2010做铜腐蚀试验，与空白样进行对照，空白样为在铜样品上不做任何防腐蚀，试验结果如表1。The experimental reagents of Examples 1 to 6 and the experimental reagents of the commercially available rust inhibitor T706 were respectively tested for copper corrosion according to GB6144-2010, and were compared with the blank sample. The blank sample was made without any anti-corrosion on the copper sample. The test results are as follows Table 1.
表1Table 1
实施例5的实验试剂与市售防锈剂T706的实验试剂对照如图1，A为实施例5的实验试剂试验样品，B为市售防锈剂T706的实验试剂试验样品。The comparison between the experimental reagent of Example 5 and the experimental reagent of the commercially available rust inhibitor T706 is shown in Figure 1. A is the experimental reagent test sample of Example 5, and B is the experimental reagent test sample of the commercially available rust inhibitor T706.
从表1和图1可知，本发明制备的苯并三氮唑衍生物缓蚀剂的防腐蚀性较佳。It can be seen from Table 1 and Figure 1 that the benzotriazole derivative corrosion inhibitor prepared by the present invention has better corrosion resistance.
以上所述实施例的各技术特征可以进行任意的组合，为使描述简洁，未对上述实施例中的各个技术特征所有可能的组合都进行描述，然而，只要这些技术特征的组合不存在矛盾，都应当认为是本说明书记载的范围。The technical features of the above-mentioned embodiments can be combined arbitrarily. In order to make the description concise, all possible combinations of the various technical features in the above-mentioned embodiments are not described. However, as long as there is no contradiction in the combination of these technical features, All should be considered as the scope of this specification.
以上所述实施例仅表达了本发明的一种实施方式，其描述较为具体和详细， 但并不能因此而理解为对发明专利范围的限制。应当指出的是，对于本领域的普通技术人员来说，在不脱离本发明构思的前提下，还可以做出若干变形和改进，这些都属于本发明的保护范围。因此，本发明专利的保护范围应以所附权利要求为准。The above-mentioned embodiment only expresses one embodiment of the present invention, and its description is relatively specific and detailed, but it should not be understood as a limitation on the scope of the invention patent. It should be pointed out that for those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can be made, and these all fall within the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention should be subject to the appended claims.
Claims (10)
- 一种苯并三氮唑衍生物缓蚀剂的制备方法，其特征在于，包括以下步骤：A preparation method of benzotriazole derivative corrosion inhibitor, which is characterized in that it comprises the following steps:将苯并三氮唑、二乙醇胺和甲醛置于在反应容器中进行混合，获得混合原料；Put benzotriazole, diethanolamine and formaldehyde in a reaction vessel for mixing to obtain mixed raw materials;边搅拌所述混合原料边升温至85℃～110℃，然后保温反应预设时间；While stirring the mixed raw materials, the temperature is raised to 85°C to 110°C, and then the temperature is kept for a predetermined time for reaction;降温至室温，获得产品。The temperature was lowered to room temperature to obtain the product.
- 根据权利要求1所述的苯并三氮唑衍生物缓蚀剂的制备方法，其特征在于，所述苯并三氮唑、二乙醇胺和甲醛的摩尔比为1～1.5：1：1～1.5。The preparation method of the benzotriazole derivative corrosion inhibitor according to claim 1, wherein the molar ratio of the benzotriazole, diethanolamine and formaldehyde is 1~1.5:1:1~1.5 .
- 根据权利要求2所述的苯并三氮唑衍生物缓蚀剂的制备方法，其特征在于，所述苯并三氮唑、二乙醇胺和甲醛的摩尔比为1.4～1.5：1：1.2～1.5。The method for preparing a benzotriazole derivative corrosion inhibitor according to claim 2, wherein the molar ratio of the benzotriazole, diethanolamine and formaldehyde is 1.4~1.5:1:1.2~1.5 .
- 根据权利要求2所述的苯并三氮唑衍生物缓蚀剂的制备方法，其特征在于，所述苯并三氮唑、二乙醇胺和甲醛的摩尔比为1.5：1：1.3～1.5。The method for preparing a benzotriazole derivative corrosion inhibitor according to claim 2, wherein the molar ratio of the benzotriazole, diethanolamine and formaldehyde is 1.5:1:1.3-1.5.
- 根据权利要求1至4任一项所述的苯并三氮唑衍生物缓蚀剂的制备方法，其特征在于，所述甲醛为37wt％～40wt％的甲醛溶液。The preparation method of a benzotriazole derivative corrosion inhibitor according to any one of claims 1 to 4, wherein the formaldehyde is a formaldehyde solution of 37 wt% to 40 wt%.
- 根据权利要求1所述的苯并三氮唑衍生物缓蚀剂的制备方法，其特征在于，所述保温反应时间为3～10小时。The method for preparing a corrosion inhibitor of benzotriazole derivatives according to claim 1, wherein the heat preservation reaction time is 3-10 hours.
- 采用权利要求1至6任一项所述的苯并三氮唑衍生物缓蚀剂的制备方法制成的苯并三氮唑衍生物缓蚀剂。A benzotriazole derivative corrosion inhibitor prepared by the method for preparing a benzotriazole derivative corrosion inhibitor according to any one of claims 1 to 6.
- 根据权利要求7所述的苯并三氮唑衍生物缓蚀剂，其特征在于，所述苯并三氮唑衍生物的结构为：The benzotriazole derivative corrosion inhibitor according to claim 7, wherein the structure of the benzotriazole derivative is:。.
- 根据权利要求7或8所述的苯并三氮唑衍生物缓蚀剂，其特征在于，所述苯并三氮唑衍生物于所述苯并三氮唑衍生物缓蚀剂中的质量含量为85％～95％。The benzotriazole derivative corrosion inhibitor according to claim 7 or 8, wherein the mass content of the benzotriazole derivative in the benzotriazole derivative corrosion inhibitor is It is 85%-95%.
- 一种如权利要求7至9任一项所述的苯并三氮唑衍生物缓蚀剂应用作为铜缓蚀剂Application of the benzotriazole derivative corrosion inhibitor according to any one of claims 7 to 9 as a copper corrosion inhibitor
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114292244A (en) * | 2022-01-06 | 2022-04-08 | 新乡市瑞丰新材料股份有限公司 | Preparation method of oleic acid modified liquid oiliness agent |
| CN115260954A (en) * | 2022-05-24 | 2022-11-01 | 江苏华海诚科新材料股份有限公司 | Sulfur-free epoxy resin composition suitable for semiconductor packaging and application |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111362883B (en) * | 2020-04-16 | 2022-04-19 | 安美科技股份有限公司 | Benzotriazole derivative corrosion inhibitor and preparation method and application thereof |
| CN112028845A (en) * | 2020-08-05 | 2020-12-04 | 长江大学 | Copper corrosion inhibitor and preparation method thereof |
| CN113620895A (en) * | 2021-09-09 | 2021-11-09 | 中国科学院兰州化学物理研究所 | Multifunctional lubricating additive and preparation method thereof |
| CN115850196A (en) * | 2022-11-29 | 2023-03-28 | 河北宝力工程装备股份有限公司 | Non-phosphorus multifunctional high-efficiency corrosion inhibitor and preparation method thereof |
| CN116460538B (en) * | 2023-04-14 | 2023-12-12 | 江苏珀然股份有限公司 | Commercial vehicle wheel forming process |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014201658A (en) * | 2013-04-04 | 2014-10-27 | ユシロ化学工業株式会社 | Water-soluble functional fluid with rot resistance |
| CN104911603A (en) * | 2015-06-19 | 2015-09-16 | 广州米奇化工有限公司 | Methylbenzotriazole derivative copper corrosion inhibitor and preparation method thereof |
| CN105621639A (en) * | 2014-11-07 | 2016-06-01 | 中国石油化工股份有限公司 | Scale-inhibiting corrosion inhibitor composition, scale-inhibiting corrosion inhibitor, and applications of scale-inhibiting corrosion inhibitor |
| CN109748879A (en) * | 2019-02-28 | 2019-05-14 | 盘锦辽河油田大力集团有限公司 | A kind of modified benzotriazole and preparation method thereof |
| CN111362883A (en) * | 2020-04-16 | 2020-07-03 | 安美科技股份有限公司 | Benzotriazole derivative corrosion inhibitor and preparation method and application thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543199A (en) * | 1984-11-16 | 1985-09-24 | Texaco Inc. | Water base hydraulic fluid |
| CN1140768A (en) * | 1995-07-15 | 1997-01-22 | 武汉水利电力大学 | Copper corrosion inhibitor and its using method |
| US7300601B2 (en) * | 2002-12-10 | 2007-11-27 | Advanced Technology Materials, Inc. | Passivative chemical mechanical polishing composition for copper film planarization |
| JP2005175218A (en) * | 2003-12-11 | 2005-06-30 | Nitta Haas Inc | Slurry for polishing copper wiring |
| CN101071278A (en) * | 2006-05-12 | 2007-11-14 | 湖南省科学技术研究开发院 | Photo resist film removing agent |
| JP2009081200A (en) * | 2007-09-25 | 2009-04-16 | Fujifilm Corp | Polishing liquid |
| KR101880306B1 (en) * | 2011-12-19 | 2018-07-20 | 동우 화인켐 주식회사 | Cleaning composition using electronic material |
| KR101957525B1 (en) * | 2012-12-31 | 2019-06-19 | 동우 화인켐 주식회사 | Photoresist stripper composition |
-
2020
- 2020-04-16 CN CN202010297846.1A patent/CN111362883B/en active Active
-
2021
- 2021-02-24 WO PCT/CN2021/077714 patent/WO2021208602A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014201658A (en) * | 2013-04-04 | 2014-10-27 | ユシロ化学工業株式会社 | Water-soluble functional fluid with rot resistance |
| CN105621639A (en) * | 2014-11-07 | 2016-06-01 | 中国石油化工股份有限公司 | Scale-inhibiting corrosion inhibitor composition, scale-inhibiting corrosion inhibitor, and applications of scale-inhibiting corrosion inhibitor |
| CN104911603A (en) * | 2015-06-19 | 2015-09-16 | 广州米奇化工有限公司 | Methylbenzotriazole derivative copper corrosion inhibitor and preparation method thereof |
| CN109748879A (en) * | 2019-02-28 | 2019-05-14 | 盘锦辽河油田大力集团有限公司 | A kind of modified benzotriazole and preparation method thereof |
| CN111362883A (en) * | 2020-04-16 | 2020-07-03 | 安美科技股份有限公司 | Benzotriazole derivative corrosion inhibitor and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| LI, JIUSHENG ET AL.: "Preparation and Tribological Studies of Borate Ester Containing Benzotriazole Group", LUBRICATING OIL, vol. 26, no. 5, 31 October 2011 (2011-10-31), pages 19 - 22, XP055859278 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114292244A (en) * | 2022-01-06 | 2022-04-08 | 新乡市瑞丰新材料股份有限公司 | Preparation method of oleic acid modified liquid oiliness agent |
| CN115260954A (en) * | 2022-05-24 | 2022-11-01 | 江苏华海诚科新材料股份有限公司 | Sulfur-free epoxy resin composition suitable for semiconductor packaging and application |
| CN115260954B (en) * | 2022-05-24 | 2024-05-28 | 江苏华海诚科新材料股份有限公司 | Sulfur-free epoxy resin composition suitable for semiconductor packaging and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111362883B (en) | 2022-04-19 |
| WO2021208602A9 (en) | 2021-11-18 |
| CN111362883A (en) | 2020-07-03 |
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