CN113121794B - Dimethyl imidazole liquefaction method - Google Patents
Dimethyl imidazole liquefaction method Download PDFInfo
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- CN113121794B CN113121794B CN201911418129.3A CN201911418129A CN113121794B CN 113121794 B CN113121794 B CN 113121794B CN 201911418129 A CN201911418129 A CN 201911418129A CN 113121794 B CN113121794 B CN 113121794B
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- dimethyl imidazole
- glycidyl ether
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- dimethyl
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Abstract
The invention relates to a method for liquefying dimethyl imidazole, which comprises the following steps: s1, mixing dimethyl imidazole, dodecylphenol and benzyl glycidyl ether, heating to 85-90 ℃ under the condition of stirring, and stirring at constant temperature until the dimethyl imidazole is completely dissolved; s2, allowing the mixture obtained in the S1 to stand until the temperature of the mixture is not increased any more; s3, adding butyl glycidyl ether into the mixture of S2, and keeping the temperature at 85-95 ℃ for 4-6 h. Wherein the mass ratio of the dimethyl imidazole to the dodecyl phenol to the benzyl glycidyl ether is 5: 2-3: 3-4, wherein the mass ratio of butyl glycidyl ether to dimethyl imidazole is 1: 2.5 to 5.
Description
Technical Field
The invention relates to the field of chemical industry, in particular to a dimethyl imidazole liquefaction method.
Background
The dimethyl imidazole has high activity and is a very good curing agent and accelerator for epoxy resin adhesives, but because the dimethyl imidazole is solid, the process for adding the dimethyl imidazole into the epoxy resin adhesives is complicated and inconvenient to use.
The invention provides a method for liquefying dimethyl imidazole, the liquefied dimethyl imidazole can be directly added into epoxy resin, the performance of the liquefied dimethyl imidazole is consistent with that of the dimethyl imidazole in a solid state, and the liquefied dimethyl imidazole can be stored for a long time without crystallization.
Disclosure of Invention
In order to achieve the purpose, the invention adopts the following technical scheme: a method for liquefying dimethyl imidazole comprises the following steps:
s1, mixing dimethyl imidazole, dodecylphenol and benzyl glycidyl ether, heating to 85-90 ℃ under the condition of stirring, and stirring at constant temperature until the dimethyl imidazole is completely dissolved;
s2, standing the mixture obtained in the step S1 until the temperature of the mixture is not increased any more;
s3, adding butyl glycidyl ether into the mixture of S2, and keeping the temperature of 85-95 ℃ for 4-6 hours;
the mass ratio of the dimethyl imidazole to the dodecyl phenol to the benzyl glycidyl ether is 5: 2-3: 3-4;
the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 1: 2.5 to 5.
Preferably, the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 3: 10.
preferably, the mass ratio of the dimethyl imidazole to the dodecyl phenol to the benzyl glycidyl ether is 5: 2: 4.
preferably, the mass ratio of the dimethyl imidazole to the dodecyl phenol to the benzyl glycidyl ether is 5: 3: 3.
the dimethyl imidazole liquefaction method provided by the invention adopts the blending of dimethyl imidazole, dodecylphenol and benzyl glycidyl ether, the blending step has mild reaction and slow heat release, and is suitable for large-batch mixing. Because the blending is slow to give off heat, it is necessary to stand until the heat of the mixture no longer rises to ensure that the mixture is uniformly mixed. And (4) dropwise adding butyl glycidyl ether, keeping the temperature at 90 ℃ for 4-6 hours after the dropwise adding is finished, and ensuring that the reaction is finished. The dimethyl imidazole solution prepared in the step S3 is a brown yellow viscous liquid, can be stored for a long time without crystallization, can be directly added and used as an epoxy resin curing agent, and has the performance consistent with that of dimethyl imidazole in a solid state.
Detailed Description
It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
The embodiment provides a method for liquefying dimethyl imidazole, which comprises the following steps:
s1, mixing dimethyl imidazole, dodecyl phenol and benzyl glycidyl ether according to the mass ratio of 5: 2: 4, mixing, heating to 90 ℃ under the condition of stirring, and then stirring at constant temperature until the dimethyl imidazole is completely dissolved;
s2, standing the mixture obtained in the step S1 until the temperature of the mixture is not increased any more;
s3, adding butyl glycidyl ether into the mixture of S2, wherein the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 3: and 10, keeping the constant temperature of 90 ℃ for 4 hours to prepare the dimethyl imidazole solution.
Example 2
The embodiment provides a method for liquefying dimethyl imidazole, which comprises the following steps:
s1, mixing dimethyl imidazole, dodecyl phenol and benzyl glycidyl ether according to the mass ratio of 5: 3: 3, mixing, heating to 85 ℃ under the condition of stirring, and then stirring at constant temperature until the dimethyl imidazole is completely dissolved;
s2, standing the mixture obtained in the step S1 until the temperature of the mixture is not increased any more;
s3, adding butyl glycidyl ether into the mixture of S2, wherein the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 3: and 10, keeping the constant temperature of 95 ℃ for 4 hours to prepare the dimethyl imidazole solution.
Example 3
The embodiment provides a method for liquefying dimethyl imidazole, which comprises the following steps:
s1, mixing dimethyl imidazole, dodecyl phenol and benzyl glycidyl ether according to the mass ratio of 5: 3: 4, mixing, heating to 87 ℃ under the stirring condition, and stirring at constant temperature until the dimethyl imidazole is completely dissolved;
s2, standing the mixture obtained in the step S1 until the temperature of the mixture is not increased any more;
s3, adding butyl glycidyl ether into the mixture of S2, wherein the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 1: 2.5, keeping the constant temperature of 85 ℃ for 6 hours to prepare the dimethyl imidazole solution.
Example 4
The embodiment provides a method for liquefying dimethyl imidazole, which comprises the following steps:
s1, mixing dimethyl imidazole, dodecyl phenol and benzyl glycidyl ether according to the mass ratio of 5: 2: 3, mixing, heating to 88 ℃ under the condition of stirring, and then stirring at constant temperature until the dimethyl imidazole is completely dissolved;
s2, standing the mixture obtained in the step S1 until the temperature of the mixture is not increased any more;
s3, adding butyl glycidyl ether into the mixture of S2, wherein the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 1: and 5, keeping the constant temperature of 94 ℃ for 5 hours to prepare the dimethyl imidazole solution.
Example 5
The embodiment provides a method for liquefying dimethyl imidazole, which comprises the following steps:
s1, mixing dimethyl imidazole, dodecyl phenol and benzyl glycidyl ether according to the mass ratio of 5: 3: 4, mixing, heating to 89 ℃ under the condition of stirring, and then stirring at constant temperature until the dimethyl imidazole is completely dissolved;
s2, standing the mixture obtained in the step S1 until the temperature of the mixture is not increased any more;
s3, adding butyl glycidyl ether into the mixture of S2, wherein the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 1: and 4, keeping the constant temperature of 90 ℃ for 6 hours to prepare the dimethyl imidazole solution.
Example 6
The embodiment provides a method for liquefying dimethyl imidazole, which comprises the following steps:
s1, mixing dimethyl imidazole, dodecyl phenol and benzyl glycidyl ether according to the mass ratio of 5: 3: 3, mixing, heating to 85 ℃ under the condition of stirring, and then stirring at constant temperature until the dimethyl imidazole is completely dissolved;
s2, standing the mixture obtained in the step S1 until the temperature of the mixture is not increased any more;
s3, adding butyl glycidyl ether into the mixture of S2, wherein the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 1: and 3, keeping the constant temperature of 89 ℃ for 6 hours to prepare the dimethyl imidazole solution.
Comparative example 1
The dimethylimidazole solutions prepared in examples 1 to 6 were stored in an incubator for 6 months, respectively, and the solution state and crystallization were observed, and the results were as follows:
according to the test result, the dimethyl imidazole solution prepared by the liquefaction method of dimethyl imidazole provided by the invention has better stability.
The dimethylimidazole solutions prepared in examples 1 to 6, which were stored for 6 months, were respectively added to epoxy resins as curing agents, and the dimethylimidazole in the existing solid state was directly added to epoxy resins as a curing agent by the prior art, and the curing time of epoxy resins was compared under the condition that the parameters of ambient humidity, temperature, and light were consistent, and the result was that the curing time of epoxy resins obtained by adding the dimethylimidazole solutions prepared in examples 1 to 6 to epoxy resins as curing agents was the same as that of epoxy resins obtained by adding dimethylimidazole in the solid state to epoxy resins. According to the comparison result, the dimethyl imidazole solution prepared by the liquefaction method of dimethyl imidazole provided by the invention has the performance consistent with that of dimethyl imidazole in a solid state as an epoxy resin curing agent.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (4)
1. A method for liquefying dimethyl imidazole is characterized by comprising the following steps:
s1, mixing dimethyl imidazole, dodecylphenol and benzyl glycidyl ether, heating to 85-90 ℃ under the condition of stirring, and stirring at constant temperature until the dimethyl imidazole is completely dissolved;
s2, standing the mixture obtained in the step S1 until the temperature of the mixture is not increased any more;
s3, adding butyl glycidyl ether into the mixture of S2, and keeping the temperature of 85-95 ℃ for 4-6 hours;
the mass ratio of the dimethyl imidazole to the dodecyl phenol to the benzyl glycidyl ether is 5: 2-3: 3-4;
the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 1: 2.5 to 5.
2. The method for liquefying dimethyl imidazole according to claim 1, wherein: the mass ratio of the butyl glycidyl ether to the dimethyl imidazole is 3: 10.
3. the method for liquefying dimethyl imidazole according to claim 2, wherein: the mass ratio of the dimethyl imidazole to the dodecyl phenol to the benzyl glycidyl ether is 5: 2: 4.
4. the method for liquefying dimethyl imidazole according to claim 2, wherein: the mass ratio of the dimethyl imidazole to the dodecyl phenol to the benzyl glycidyl ether is 5: 3: 3.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3756984A (en) * | 1968-03-04 | 1973-09-04 | Shell Oil Co | Epoxy imidazole adducts as curing agents for epoxy resins |
| EP0118270A2 (en) * | 1983-03-03 | 1984-09-12 | INTEREZ, Inc.(a Delaware corporation) | Modified imidazole curing agent catalyst for epoxy resins |
| JPH01174520A (en) * | 1987-12-29 | 1989-07-11 | Koei Chem Co Ltd | Curing agent for epoxy resin |
| JP2002088137A (en) * | 2000-09-14 | 2002-03-27 | Sanwa Chemical Industry Co Ltd | Low-temperature curing latent curable agent for epoxy resin |
| CN1931889A (en) * | 2006-09-27 | 2007-03-21 | 蓝星化工新材料股份有限公司无锡树脂厂 | Modified solid imidazole curing agent and its modification process |
| JP2019099754A (en) * | 2017-12-07 | 2019-06-24 | 株式会社Ｔ＆Ｋ Ｔｏｋａ | Latent curing agent and one-pack curable epoxide composition containing the same |
-
2019
- 2019-12-31 CN CN201911418129.3A patent/CN113121794B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3756984A (en) * | 1968-03-04 | 1973-09-04 | Shell Oil Co | Epoxy imidazole adducts as curing agents for epoxy resins |
| EP0118270A2 (en) * | 1983-03-03 | 1984-09-12 | INTEREZ, Inc.(a Delaware corporation) | Modified imidazole curing agent catalyst for epoxy resins |
| JPH01174520A (en) * | 1987-12-29 | 1989-07-11 | Koei Chem Co Ltd | Curing agent for epoxy resin |
| JP2002088137A (en) * | 2000-09-14 | 2002-03-27 | Sanwa Chemical Industry Co Ltd | Low-temperature curing latent curable agent for epoxy resin |
| CN1931889A (en) * | 2006-09-27 | 2007-03-21 | 蓝星化工新材料股份有限公司无锡树脂厂 | Modified solid imidazole curing agent and its modification process |
| JP2019099754A (en) * | 2017-12-07 | 2019-06-24 | 株式会社Ｔ＆Ｋ Ｔｏｋａ | Latent curing agent and one-pack curable epoxide composition containing the same |
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