CN112745481A - Imidazolyl-modified epoxy resin curing agent and preparation method thereof - Google Patents
Imidazolyl-modified epoxy resin curing agent and preparation method thereof Download PDFInfo
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- CN112745481A CN112745481A CN202011580858.1A CN202011580858A CN112745481A CN 112745481 A CN112745481 A CN 112745481A CN 202011580858 A CN202011580858 A CN 202011580858A CN 112745481 A CN112745481 A CN 112745481A
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- epoxy resin
- curing agent
- imidazolyl
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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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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Abstract
The invention discloses an imidazolyl group modified epoxy resin curing agent and a preparation method thereof, wherein the method comprises the following steps: performing addition reaction on epoxy resin and isophorone diamine for 5-7h at the reaction temperature of 50-70 ℃; adding butyl glycidyl ether, methyl phenyl ene carboxylic acid, acid anhydride and polypropylene glycol diglycidyl ether, uniformly mixing, and reacting for 30-40 min; adding dimethyl imidazole, and stirring for reaction for 1-2 h. The invention has the following beneficial effects: the epoxy resin curing agent modified by the imidazolyl has good thermal conductivity and wider application range.
Description
Technical Field
The invention belongs to the field of curing agents, and particularly relates to an imidazolyl-modified epoxy resin curing agent and a preparation method thereof.
Background
Epoxy resins must react with curing agents to form three-dimensional structures to be of practical value. Therefore, the structure and quality of the curing agent will directly affect the application effect of the epoxy resin. Each development of a new curing agent can solve one aspect of the problem, which is equivalent to the development of a new epoxy resin or the development of a new use of the epoxy resin. Therefore, the development of new curing agents is far more important than the development of new epoxy resins.
Chinese patent application No. CN201910439356.8 discloses an epoxy resin curing agent, which introduces mesogen into the curing agent, and uses the epoxy resin curing agent to cure the epoxy resin, thereby improving the thermal conductivity of the formed epoxy resin composition. The epoxy resin curing agent disclosed by the invention also has good compatibility with epoxy resin. The invention provides a curing agent with more excellent thermal conductivity.
Disclosure of Invention
The invention provides an imidazole-based modified epoxy resin curing agent and a preparation method thereof, aiming at solving the problems of the prior art, and the curing agent has good thermal conductivity and wide application range.
In order to solve the technical problems, the invention adopts the following technical scheme:
the imidazolyl group modified epoxy resin curing agent comprises the following raw materials in parts by weight: 30-35 parts of isophorone diamine, 20-30 parts of epoxy resin, 30-60 parts of butyl glycidyl ether, 10-20 parts of dimethyl imidazole, 20-30 parts of methyl toluenedicarboxylate, 10-30 parts of anhydride and 30-40 parts of polypropylene glycol diglycidyl ether.
Preferably, the imidazolyl-modified epoxy resin curing agent comprises the following raw materials in parts by weight: 32 parts of isophorone diamine, 25 parts of epoxy resin, 40 parts of butyl glycidyl ether, 15 parts of dimethyl imidazole, 25 parts of methyl toluenedicarboxylate, 20 parts of anhydride and 35 parts of polypropylene glycol diglycidyl ether.
Preferably, the imidazolyl-modified epoxy resin curing agent comprises the following raw materials in parts by weight: 30 parts of isophorone diamine, 20 parts of epoxy resin, 30 parts of butyl glycidyl ether, 10 parts of dimethyl imidazole, 20 parts of methyl methylphenylcarboxylate, 10 parts of anhydride and 30 parts of polypropylene glycol diglycidyl ether.
Preferably, the imidazolyl-modified epoxy resin curing agent comprises the following raw materials in parts by weight: 35 parts of isophorone diamine, 30 parts of epoxy resin, 60 parts of butyl glycidyl ether, 20 parts of dimethyl imidazole, 30 parts of methyl toluenedicarboxylate, 30 parts of anhydride and 40 parts of polypropylene glycol diglycidyl ether.
Preferably, the imidazolyl-modified epoxy resin curing agent comprises the following raw materials in parts by weight: 31 parts of isophorone diamine, 27 parts of epoxy resin, 39 parts of butyl glycidyl ether, 17 parts of dimethyl imidazole, 23 parts of methyl toluenedicarboxylate, 19 parts of anhydride and 35 parts of polypropylene glycol diglycidyl ether.
Preferably, the amount of dimethylimidazole added is 50% of the amount of epoxy resin added.
The preparation method of the imidazolyl group modified epoxy resin curing agent comprises the following steps: performing addition reaction on epoxy resin and isophorone diamine for 5-7h at the reaction temperature of 50-70 ℃; adding butyl glycidyl ether, methyl phenyl ene carboxylic acid, acid anhydride and polypropylene glycol diglycidyl ether, uniformly mixing, and reacting for 30-40 min; adding dimethyl imidazole, and stirring for reaction for 1-2 h.
The invention has the following beneficial effects: the epoxy resin curing agent modified by the imidazolyl has good thermal conductivity and wider application range.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
Example 1
The imidazolyl group modified epoxy resin curing agent comprises the following raw materials in parts by weight: 32 parts of isophorone diamine, 25 parts of epoxy resin, 40 parts of butyl glycidyl ether, 15 parts of dimethyl imidazole, 25 parts of methyl toluenedicarboxylate, 20 parts of anhydride and 35 parts of polypropylene glycol diglycidyl ether.
The preparation method of the imidazolyl group modified epoxy resin curing agent comprises the following steps: performing addition reaction on epoxy resin and isophorone diamine for 6h at the reaction temperature of 50-70 ℃; adding butyl glycidyl ether, methyl phenyl ene carboxylic acid, acid anhydride and polypropylene glycol diglycidyl ether, uniformly mixing, and reacting for 35 min; adding dimethyl imidazole, and stirring to react for 1.5 h.
Example 2
The imidazolyl group modified epoxy resin curing agent comprises the following raw materials in parts by weight: 30 parts of isophorone diamine, 20 parts of epoxy resin, 30 parts of butyl glycidyl ether, 10 parts of dimethyl imidazole, 20 parts of methyl methylphenylcarboxylate, 10 parts of anhydride and 30 parts of polypropylene glycol diglycidyl ether.
17 parts of dimethyl imidazole, 23 parts of methyl phenyl ene carboxylate, 19 parts of acid anhydride and 35 parts of polypropylene glycol diglycidyl ether.
The preparation method of the imidazolyl group modified epoxy resin curing agent comprises the following steps: performing addition reaction on epoxy resin and isophorone diamine for 5h at the reaction temperature of 50-70 ℃; adding butyl glycidyl ether, methyl phenyl ene carboxylic acid, acid anhydride and polypropylene glycol diglycidyl ether, uniformly mixing, and reacting for 30 min; adding dimethyl imidazole, and stirring for reaction for 1 h.
Example 3
The imidazolyl group modified epoxy resin curing agent comprises the following raw materials in parts by weight: 35 parts of isophorone diamine, 30 parts of epoxy resin, 60 parts of butyl glycidyl ether, 20 parts of dimethyl imidazole, 30 parts of methyl toluenedicarboxylate, 30 parts of anhydride and 40 parts of polypropylene glycol diglycidyl ether.
The preparation method of the imidazolyl group modified epoxy resin curing agent comprises the following steps: performing addition reaction on epoxy resin and isophorone diamine for 7h at the reaction temperature of 50-70 ℃; adding butyl glycidyl ether, methyl phenyl ene carboxylic acid, acid anhydride and polypropylene glycol diglycidyl ether, uniformly mixing, and reacting for 40 min; adding dimethyl imidazole, and stirring for reaction for 2 hours.
Example 4
The imidazolyl group modified epoxy resin curing agent comprises the following raw materials in parts by weight: 31 parts of isophorone diamine, 27 parts of epoxy resin, 39 parts of butyl glycidyl ether, 17 parts of dimethyl imidazole, 23 parts of methyl toluenedicarboxylate, 19 parts of anhydride and 35 parts of polypropylene glycol diglycidyl ether.
The preparation method of the imidazolyl group modified epoxy resin curing agent comprises the following steps: performing addition reaction on epoxy resin and isophorone diamine for 5h at the reaction temperature of 50-70 ℃; adding butyl glycidyl ether, methyl phenyl ene carboxylic acid, acid anhydride and polypropylene glycol diglycidyl ether, uniformly mixing, and reacting for 38 min; adding dimethyl imidazole, and stirring to react for 1.2 h.
Comparative example 1
The difference from example 1 is that: dimethyl imidazole was not added.
And (3) performance testing:
as can be seen from the table, the epoxy resin curing agent modified by the imidazolyl has good thermal conductivity.
The above description is only a preferred embodiment of the present invention, and the scope of the present invention is not limited thereto, and any simple changes or equivalent substitutions of the technical solutions that can be obviously obtained by those skilled in the art within the technical scope of the present invention are within the scope of the present invention.
Claims (7)
1. The imidazolyl group modified epoxy resin curing agent is characterized by comprising the following raw materials in parts by weight: 30-35 parts of isophorone diamine, 20-30 parts of epoxy resin, 30-60 parts of butyl glycidyl ether, 10-20 parts of dimethyl imidazole, 20-30 parts of methyl toluenedicarboxylate, 10-30 parts of anhydride and 30-40 parts of polypropylene glycol diglycidyl ether.
2. The imidazolyl-modified epoxy resin curing agent according to claim 1, which comprises the following raw materials in parts by weight: 32 parts of isophorone diamine, 25 parts of epoxy resin, 40 parts of butyl glycidyl ether, 15 parts of dimethyl imidazole, 25 parts of methyl toluenedicarboxylate, 20 parts of anhydride and 35 parts of polypropylene glycol diglycidyl ether.
3. The imidazolyl-modified epoxy resin curing agent according to claim 1, which comprises the following raw materials in parts by weight: 35 parts of isophorone diamine, 30 parts of epoxy resin, 60 parts of butyl glycidyl ether, 20 parts of dimethyl imidazole, 30 parts of methyl toluenedicarboxylate, 30 parts of anhydride and 40 parts of polypropylene glycol diglycidyl ether.
4. The imidazolyl-modified epoxy resin curing agent according to claim 1, which comprises the following raw materials in parts by weight: 30 parts of isophorone diamine, 20 parts of epoxy resin, 30 parts of butyl glycidyl ether, 10 parts of dimethyl imidazole, 20 parts of methyl methylphenylcarboxylate, 10 parts of anhydride and 30 parts of polypropylene glycol diglycidyl ether.
5. The imidazolyl-modified epoxy resin curing agent according to claim 1, which comprises the following raw materials in parts by weight: 31 parts of isophorone diamine, 27 parts of epoxy resin, 39 parts of butyl glycidyl ether, 17 parts of dimethyl imidazole, 23 parts of methyl toluenedicarboxylate, 19 parts of anhydride and 35 parts of polypropylene glycol diglycidyl ether.
6. The imidazolyl-modified epoxy resin curing agent of claim 1, wherein the dimethylimidazole is added in an amount of 50% of the epoxy resin.
7. The method for preparing the imidazolyl-modified epoxy resin curing agent according to claim 1, comprising the steps of: performing addition reaction on epoxy resin and isophorone diamine for 5-7h at the reaction temperature of 50-70 ℃; adding butyl glycidyl ether, methyl phenyl ene carboxylic acid, acid anhydride and polypropylene glycol diglycidyl ether, uniformly mixing, and reacting for 30-40 min; adding dimethyl imidazole, and stirring for reaction for 1-2 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011580858.1A CN112745481A (en) | 2020-12-28 | 2020-12-28 | Imidazolyl-modified epoxy resin curing agent and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202011580858.1A CN112745481A (en) | 2020-12-28 | 2020-12-28 | Imidazolyl-modified epoxy resin curing agent and preparation method thereof |
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| CN112745481A true CN112745481A (en) | 2021-05-04 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190719A (en) * | 1977-07-04 | 1980-02-26 | Mitsubishi Petrochemical Company Limited | Imidazolidone polyamines as epoxy curing agents |
| JPH06157718A (en) * | 1992-11-26 | 1994-06-07 | Mitsubishi Petrochem Co Ltd | Epoxy resin composition for casting and cast-molded article of the resin |
| JPH06271649A (en) * | 1993-03-19 | 1994-09-27 | Mitsubishi Petrochem Co Ltd | Casting epoxy resin composition and its cast material |
| CN105837797A (en) * | 2016-04-08 | 2016-08-10 | 苏州圣杰特种树脂有限公司 | A water-based epoxy resin curing agent |
| US20180355096A1 (en) * | 2017-06-09 | 2018-12-13 | Hexion Inc. | Epoxy resin systems for composites |
| CN111072924A (en) * | 2018-10-22 | 2020-04-28 | 南京中赢纳米新材料有限公司 | Modified epoxy resin curing agent |
-
2020
- 2020-12-28 CN CN202011580858.1A patent/CN112745481A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190719A (en) * | 1977-07-04 | 1980-02-26 | Mitsubishi Petrochemical Company Limited | Imidazolidone polyamines as epoxy curing agents |
| JPH06157718A (en) * | 1992-11-26 | 1994-06-07 | Mitsubishi Petrochem Co Ltd | Epoxy resin composition for casting and cast-molded article of the resin |
| JPH06271649A (en) * | 1993-03-19 | 1994-09-27 | Mitsubishi Petrochem Co Ltd | Casting epoxy resin composition and its cast material |
| CN105837797A (en) * | 2016-04-08 | 2016-08-10 | 苏州圣杰特种树脂有限公司 | A water-based epoxy resin curing agent |
| US20180355096A1 (en) * | 2017-06-09 | 2018-12-13 | Hexion Inc. | Epoxy resin systems for composites |
| CN111072924A (en) * | 2018-10-22 | 2020-04-28 | 南京中赢纳米新材料有限公司 | Modified epoxy resin curing agent |
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