CN112724372A - Epoxy resin low-temperature curing agent and epoxy resin adhesive - Google Patents
Epoxy resin low-temperature curing agent and epoxy resin adhesive Download PDFInfo
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- CN112724372A CN112724372A CN202011566522.XA CN202011566522A CN112724372A CN 112724372 A CN112724372 A CN 112724372A CN 202011566522 A CN202011566522 A CN 202011566522A CN 112724372 A CN112724372 A CN 112724372A
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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
- C08G59/66—Mercaptans
-
- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4085—Curing agents not provided for by the groups C08G59/42 - C08G59/66 silicon containing compounds
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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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/22—Expanded, porous or hollow particles
- C08K7/24—Expanded, porous or hollow particles inorganic
- C08K7/26—Silicon- containing compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention provides an epoxy resin low-temperature curing agent which comprises the following components in parts by weight: polythiol: 40-80 parts of terminal methacrylate group silanol: 0.1-20 parts of white carbon black: 0.01-1 part of accelerator: 0.5-10 parts of calcium carbonate: 10-55 parts. According to the invention, the polythiol is modified by using the terminal methacrylate-based silanol, and the curing agent prepared by using the terminal methacrylate-based silanol can reduce the curing condition of the epoxy resin and has excellent high temperature resistance. Experimental results show that the curing agent prepared by the invention and epoxy resin have shear strength of more than 15.0MPa after curing, the curing agent is placed for 24 hours at 80 ℃, the shear strength has no obvious change, the shear strength is high, and the high temperature resistance is good. The invention also provides an epoxy resin adhesive.
Description
Technical Field
The invention belongs to the technical field of high polymer resin, and particularly relates to an epoxy resin low-temperature curing agent and an epoxy resin adhesive.
Background
The epoxy resin adhesive is one of the most important adhesives at present, and has the advantages of low volatile matter during curing, small shrinkage, high bonding strength, good performance, good solvent resistance and water resistance, environmental aging resistance, excellent electrochemical performance and the like, so that the epoxy resin adhesive plays an important role in synthesizing the adhesive. The epoxy resin curing agent can be used as building structural adhesive, electronic packaging adhesive and the like with excellent performance after crosslinking reaction. Because the raw materials are sufficient and easily available, the preparation process is skillful, simple, convenient and feasible, the performance is excellent, the functions are various, and the application is extremely wide.
According to the application requirements of low-temperature curing and rapid curing of people, the low-temperature or room-temperature curing agent comes along, the curing agent mainly comprises thiol curing agents and can be rapidly cured at the temperature of-10-40 ℃, and the problems of long curing time, high curing temperature and the like of adhesives in the fields of electronics, decoration, medical use and the like are solved due to the appearance of the curing agent.
The thiol curing agent is used as a novel epoxy resin curing agent, has a plurality of high-activity group sulfydryl on the terminal group, can be crosslinked and cured with epoxy resin, and has the advantages of low curing temperature, rapid curing and the like. However, the thiol curing agent has a fast curing rate at low temperature, and particularly after partial end groups react with each other, the molecular weight is relatively increased, so that unreacted molecules or active end groups are relatively positioned, the reaction degree is reduced, and the adhesive is brittle and has insufficient high temperature resistance and durability.
Disclosure of Invention
The invention aims to provide an epoxy resin low-temperature curing agent and an epoxy resin adhesive.
The invention provides an epoxy resin low-temperature curing agent which comprises the following components in parts by weight:
polythiol: 40-80 parts of terminal methacrylate group silanol: 0.1-20 parts of white carbon black: 0.01-1 part of accelerator: 0.5-10 parts of calcium carbonate: 10-55 parts.
Preferably, the polythiol has a structure represented by formula I or formula II:
HS-R1-X-R2-SH formula II;
in the formula I, R is selected from C-, CH-and CH2-, -COH-or CSH-; n is more than or equal to 0 and less than or equal to 5, m is more than or equal to 2 and less than or equal to 4;
in the formula II, R1、R2Independently selected from C1-C10 fatty alkyl, C1-C10 fatty aldehyde group, C1-C10 fatty ester group or C1-C10 fatty ketone group; x is selected from one of-S-, -C-, -Si-, -CSH-, -COH-.
Preferably, the terminal methacrylate-based silanol has a structure represented by formula III:
wherein X is an integer of 1-10.
Preferably, the white carbon black is hydrophilic silicon dioxide with the particle size of 5-100 nm.
Preferably, the accelerator is 2, 4, 6-tris (dimethylaminomethyl) phenol.
The invention provides an epoxy resin adhesive, which is characterized by comprising epoxy resin and a curing agent;
the curing agent is the epoxy resin low-temperature curing agent described above.
Preferably, the mass ratio of the epoxy resin to the curing agent is (0.5-2): (0.5-2).
The invention provides an epoxy resin low-temperature curing agent which comprises the following components in parts by weight: polythiol: 40-80 parts of terminal methacrylate group silanol: 0.1-20 parts of white carbon black: 0.01-1 part of accelerator: 0.5-10 parts of calcium carbonate: 10-55 parts. According to the invention, the polythiol is modified by using the terminal methacrylate-based silanol, and the curing agent prepared by using the terminal methacrylate-based silanol can reduce the curing condition of the epoxy resin and has excellent high temperature resistance. Experimental results show that the curing agent prepared by the invention and epoxy resin have shear strength of more than 15.0MPa after curing, the curing agent is placed for 24 hours at 80 ℃, the shear strength has no obvious change, the shear strength is high, and the high temperature resistance is good.
Detailed Description
The invention provides an epoxy resin low-temperature curing agent which comprises the following components in parts by weight:
polythiol: 40-80 parts of terminal methacrylate group silanol: 0.1-20 parts of white carbon black: 0.01-1 part of accelerator: 0.5-10 parts of calcium carbonate: 10-55 parts.
In the present invention, the weight portion of the polythiol is preferably 40 to 80 parts, preferably 45 to 75 parts, more preferably 50 to 70 parts, such as 40 parts, 45 parts, 50 parts, 55 parts, 60 parts, 65 parts, 70 parts, 75 parts, 80 parts, and preferably any of the above values is an upper limit or a lower limit.
The polythiol has a structure represented by formula I or formula II:
HS-R1-X-R2-SH formula II;
in the formula I, R is selected from C-, CH-and CH2-、-COCH2-or CSH-, n may be 0, 1, 2, 3, 4 or 5; m may be 2, 3 or 4.
In the formula II, R1、R2Independently selected from C1-C10 fatty alkyl, C1-C10 fatty aldehyde group, C1-C10 fatty ester group or C1-C10 fatty ketone group, preferably C2-C8 fatty alkyl, C2-C8 fatty aldehyde group, C2-C8 fatty ester group or C2-C8 fatty ketone group, more preferably C2-C5 fatty alkyl, C2-C5 fatty aldehyde group, C2-C5 fatty ester group or C2-C5 fatty ketone group, and concretely, in the embodiment of the invention, the fatty alkyl group can be ethyl or isoamyl.
In the formula II, X is selected from one of-S-, -C-, -Si-, -CSH-and-COH-.
In the present invention, the weight part of the terminal methacrylate-based silanol is preferably 0.1 to 20 parts, more preferably 1 to 15 parts, such as 0.1 part, 1 part, 2 parts, 3 parts, 4 parts, 5 parts, 6 parts, 7 parts, 8 parts, 9 parts, 10 parts, 11 parts, 12 parts, 13 parts, 14 parts, 15 parts, 16 parts, 17 parts, 18 parts, 19 parts, 20 parts, and preferably a range value in which any of the above values is an upper limit or a lower limit.
The terminal methacrylate-based silanol has a structure shown in formula III:
wherein, X is an integer of 1-10, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
In the present invention, the white carbon is preferably hydrophilic silica having a particle size of 5 to 100nm, and the weight fraction of the white carbon is preferably 0.01 to 1 part, more preferably 0.1 to 0.8 part, such as 0.01 part, 0.05 part, 0.1 part, 0.2 part, 0.3 part, 0.4 part, 0.5 part, 0.6 part, 0.7 part, 0.8 part, 0.9 part, 1.0 part, and preferably a range value in which any of the above values is an upper limit or a lower limit.
In the present invention, the accelerator is preferably 2, 4, 6-tris (dimethylaminomethyl) phenol, and the weight part of the accelerator is preferably 0.5 to 10 parts, more preferably 1 to 8 parts, such as 0.5 part, 1.0 part, 0.9 part, 1.5 parts, 2 parts, 2.5 parts, 3.0 parts, 3.5 parts, 4.0 parts, 4.5 parts, 5.0 parts, 5.5 parts, 6.0 parts, 6.5 parts, 7.0 parts, 7.5 parts, 8.0 parts, 8.5 parts, 9.0 parts, 9.5 parts, 10 parts, and preferably any of the above values is a range of upper limit or lower limit.
In the present invention, the calcium carbonate is preferably analytically pure calcium carbonate, and the weight part of the calcium carbonate is preferably 10 to 55 parts, more preferably 20 to 50 parts, such as 10 parts, 15 parts, 20 parts, 25 parts, 30 parts, 35 parts, 40 parts, 45 parts, 50 parts, and 55 parts, and preferably any of the above values is a range with an upper limit or a lower limit.
The invention also provides an epoxy resin adhesive which is characterized by comprising epoxy resin and the epoxy resin low-temperature curing agent.
In the invention, the mass ratio of the curing agent epoxy resin to the curing agent is (0.5-2): (0.5-2), preferably (0.5-2): (1-1.2), most preferably (1.2-1): (1-1.2), such as 1:1, 1:1.2 or 1.2: 1.
In the invention, corresponding functional additives, such as a toughening agent, a plasticizer, a diluent, an accelerator, an antioxidant, a filler, a coupling agent and the like, can be added to the epoxy resin adhesive according to actual needs, and the specific type and the amount of the functional additives can refer to the type and the amount of common additives in the field, which is not described herein again.
The invention provides an epoxy resin low-temperature curing agent which comprises the following components in parts by weight: polythiol: 40-80 parts of terminal methacrylate group silanol: 0.1-20 parts of white carbon black: 0.01-1 part of accelerator: 0.5-10 parts of calcium carbonate: 10-55 parts. According to the invention, the polythiol is modified by using the terminal methacrylate-based silanol, and the curing agent prepared by using the terminal methacrylate-based silanol can reduce the curing condition of the epoxy resin and has excellent high temperature resistance. Experimental results show that the curing agent prepared by the invention and epoxy resin have shear strength of more than 15.0MPa after curing, the curing agent is placed for 24 hours at 80 ℃, the shear strength has no obvious change, the shear strength is high, and the high temperature resistance is good.
In order to further illustrate the present invention, the following examples are provided to describe the epoxy resin low temperature curing agent and the epoxy resin adhesive in detail, but should not be construed as limiting the scope of the present invention.
Example 1:
polythiol: 80 portions
Terminal methacrylate-based silanol: 5 portions of
Hydrophilic silica with a particle size of 5 nm: 1 part of
2, 4, 6-tris (dimethylaminomethyl) phenol: 4 portions of
Komi analytical pure calcium carbonate: 10 parts.
The polythiol has the following structure:
HS-R1-X-R2-SH；
wherein R is1Is ethyl, R2Is isoamyl, and X is-C-.
The terminal methacrylate-based silanol has the following structure:
Example 2
Polythiol: 60 portions of
Terminal methacrylate-based silanol: 18 portions of
Hydrophilic silica with a particle size of 5 nm: 0.5 portion
2, 4, 6-tris (dimethylaminomethyl) phenol: 1.5 parts of
Komi analytical pure calcium carbonate: and 20 parts.
The polythiol has the following structure:
wherein R is-CSH-structure, n is 1, m is 3;
the terminal methacrylate-based silanol has the following structure:
x is 7.
Example 3
Polythiol: 40 portions of
Terminal methacrylate-based silanol: 19 portions of
Hydrophilic silica with a particle size of 5 nm: 0.1 part
2, 4, 6-tris (dimethylaminomethyl) phenol: 0.9 portion
Komi analytical pure calcium carbonate: 40 parts of the components.
The polythiol has the following structure:
wherein R is-COH-structure, n is 5, m is 2;
the terminal methacrylate-based silanol has the following structure:
Examples 4 to 6
The epoxy resin adhesives are prepared by mixing the curing agents of examples 1-3 with epoxy resin according to the mixture ratio in table 1, and the performance test is shown in table 1.
TABLE 1 formulation and Properties of epoxy adhesives in examples 4-6
| Curing agent | Example 1 | Example 2 | Example 3 |
| Epoxy resin | E51 | E44 | E54 |
| Curing agent: epoxy resin (mass ratio) | 1:1 | 1:1.2 | 1.2:1 |
| Shear strength/MPa | 16.7 | 15.1 | 17.3 |
| Shear strength after high temperature/MPa | 16.6 | 15.0 | 17.3.0 |
Test results prove that the shear strength of the curing agent prepared by the invention and the epoxy resin after curing is more than 15.0MPa, the curing agent is placed for 24 hours at the temperature of 80 ℃, the shear strength has no obvious change, the shear strength is high, and the high temperature resistance is good.
According to the GB/T7124-;
after the prepared sample is placed at 80 ℃ for 24 hours, the strength detection is carried out according to the method, the adhesive still has high adhesive force and bonding strength, and the fact that the curing agent and the epoxy resin are compounded has high-temperature resistance is shown, and long-term application under the high-temperature condition of 80 ℃ can be met.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (7)
1. An epoxy resin low-temperature curing agent comprises the following components in parts by weight:
polythiol: 40-80 parts of terminal methacrylate group silanol: 0.1-20 parts of white carbon black: 0.01-1 part of accelerator: 0.5-10 parts of calcium carbonate: 10-55 parts.
2. The epoxy resin low-temperature curing agent according to claim 1, wherein the polythiol has a structure represented by formula I or formula II:
HS-R1-X-R2-SH formula II;
in the formula I, R is selected from C-, CH-and CH2-, -COH-or CSH-; n is more than or equal to 0 and less than or equal to 5, m is more than or equal to 2 and less than or equal to 4;
in the formula II, R1、R2Independently selected from C1-C10 fatty alkyl, C1-C10 fatty aldehyde group, C1-C10 fatty ester group or C1-C10 fatty ketone group; x is selected from one of-S-, -C-, -Si-, -CSH-, -COH-.
3. The epoxy resin low-temperature curing agent according to claim 1, wherein the terminal methacrylate-based silanol has a structure represented by formula III:
wherein X is an integer of 1-10.
4. The epoxy resin low-temperature curing agent according to claim 1, wherein the white carbon black is hydrophilic silica with a particle size of 5-100 nm.
5. The low temperature epoxy resin curing agent of claim 1, wherein the accelerator is 2, 4, 6-tris (dimethylaminomethyl) phenol.
6. An epoxy resin adhesive is characterized by comprising epoxy resin and a curing agent;
the curing agent is the epoxy resin low-temperature curing agent as defined in any one of claims 1 to 5.
7. The epoxy resin adhesive according to claim 6, wherein the mass ratio of the epoxy resin to the curing agent is (0.5-2): (0.5-2).
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011566522.XA CN112724372A (en) | 2020-12-25 | 2020-12-25 | Epoxy resin low-temperature curing agent and epoxy resin adhesive |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202011566522.XA CN112724372A (en) | 2020-12-25 | 2020-12-25 | Epoxy resin low-temperature curing agent and epoxy resin adhesive |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114479731A (en) * | 2021-12-27 | 2022-05-13 | 烟台信友新材料有限公司 | High-weather-resistance, anti-corrosion and anti-impact low-temperature curing adhesive and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3946059A (en) * | 1973-12-05 | 1976-03-23 | Dynamit Nobel Aktiengesellschaft | Method of preparing alkylalkoxysilanes containing polysulfide bridges |
| US4895910A (en) * | 1987-03-09 | 1990-01-23 | Kansai Paint Company, Limited | Resin composition curable at low temperature |
-
2020
- 2020-12-25 CN CN202011566522.XA patent/CN112724372A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3946059A (en) * | 1973-12-05 | 1976-03-23 | Dynamit Nobel Aktiengesellschaft | Method of preparing alkylalkoxysilanes containing polysulfide bridges |
| US4895910A (en) * | 1987-03-09 | 1990-01-23 | Kansai Paint Company, Limited | Resin composition curable at low temperature |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114479731A (en) * | 2021-12-27 | 2022-05-13 | 烟台信友新材料有限公司 | High-weather-resistance, anti-corrosion and anti-impact low-temperature curing adhesive and preparation method thereof |
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