CN107022336B - Modified organic silicon adhesive and preparation method thereof - Google Patents
Modified organic silicon adhesive and preparation method thereof Download PDFInfo
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- CN107022336B CN107022336B CN201710227721.XA CN201710227721A CN107022336B CN 107022336 B CN107022336 B CN 107022336B CN 201710227721 A CN201710227721 A CN 201710227721A CN 107022336 B CN107022336 B CN 107022336B
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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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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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
- C09J11/06—Non-macromolecular additives organic
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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
- C09J11/08—Macromolecular additives
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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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
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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
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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Abstract
The invention belongs to the technical field of high polymer materials, and discloses a modified organic silicon adhesive and a preparation method thereof. The organic silicon adhesive provided by the invention comprises the following components in parts by weight: 15-20 parts of amine compounds, 20-25 parts of epoxy resin compounds, 20-30 parts of polysiloxane, 2-4 parts of flexibilizer, 0.001-0.005 part of platinum catalyst and 1-2 parts of curing agent. The modified organic silicon adhesive simultaneously comprises an amine compound component and an epoxy resin compound component, wherein the amine compound and the epoxy resin compound generate addition reaction to modify the epoxy resin compound, so that the cured adhesive not only has high bonding strength, but also has good thermal stability, and can be widely applied to industries such as aerospace, ships, automobiles, electronic products, buildings and the like.
Description
Technical Field
The invention relates to the technical field of high polymer materials, in particular to a modified organic silicon adhesive and a preparation method thereof.
Background
In the 20 th century and the 50 th century, with the development of military affairs, structural members of airplanes, missiles, spacecrafts and the like all need adhesives capable of working for a long time under the condition of high-temperature loading. In order to meet the needs of the aviation and electronic industries, many researchers have developed high temperature adhesives. The high temperature resistance of the adhesive is evaluated according to the adhesive strength or certain strength retention rate which can keep the design requirement in specific temperature, time and medium, namely the high temperature resistant adhesive must meet the following requirements: 1) the thermal weight loss temperature is high, the thermal deformation temperature and the decomposition temperature are high, and the thermal physical and thermal chemical properties are good; 2) under the working condition of higher temperature, the adhesive has better physical and mechanical properties and higher adhesive strength, and can maintain the properties within the specified time; 3) good processability; 4) the heat resistance under the temperature cycle change is better, and the test of high temperature can be endured in a short time.
The organic silicon adhesive has excellent adhesive property and high temperature resistance, and is widely applied to the industries of aerospace, ships, automobiles, electronic products, buildings and the like. As with other adhesives, in order to achieve a good bonding effect when an adherend is bonded with a silicone adhesive, two conditions must be provided: firstly, the adhesive is required to be capable of wetting the surface of an adherend well; secondly, the adhesive and the adherend need to have strong mutual bonding force. In the preparation of the existing organic silicon adhesive, the defects of easy generation of bubbles, poor extreme temperature (high temperature and low temperature) resistance and the like exist in the cementing process, so that the existing organic silicon adhesive rarely has excellent cementing property and high heat resistance.
Disclosure of Invention
The present invention aims to provide a modified silicone adhesive having excellent adhesive properties and high heat resistance, in view of the above-mentioned disadvantages of the prior art.
The invention also aims to provide a preparation method of the modified organic silicon adhesive.
In order to solve the technical problems, the embodiment of the invention provides a modified silicone adhesive, which comprises the following components in parts by weight: 15-20 parts of amine compounds, 20-25 parts of epoxy resin compounds, 20-30 parts of polysiloxane, 2-4 parts of flexibilizer, 0.001-0.005 part of platinum catalyst and 1-2 parts of curing agent.
Compared with the prior art, the modified organic silicon adhesive provided by the embodiment of the invention is characterized by simultaneously containing an amine compound component and an epoxy resin compound component. As a raw material component of the organic silicon adhesive, the epoxy resin has low shrinkage, high bonding strength and excellent electrical property, but the cured product has poor high-temperature resistance and is not used in a high-temperature environment, so that the epoxy resin needs to be modified to enhance the thermal stability. Therefore, the amine compound is added simultaneously in the embodiment of the invention, and the amine compound can perform addition reaction with the epoxy resin compound to modify the epoxy resin compound well, so that the cured adhesive not only has high bonding strength, but also has high thermal stability. The modified organic silicon adhesive has excellent adhesive property and high heat resistance, and can be widely applied to the industries of aerospace, ships, automobiles, electronic products, buildings and the like.
Preferably, in the modified silicone adhesive provided by the embodiment of the present invention, the amine compound added is benzimidazole. Benzene rings and nitrogen atoms contained in the molecular structure of benzimidazole make it exhibit good heat resistance, but have little adhesion; the epoxy resin compounds are just substances with good toughness and high bonding strength but poor heat resistance, and the addition of the benzimidazole increases the content of benzene rings in an organic silicon adhesive system, and improves the heat resistance and the toughness of the system. In the process of mixing reaction of benzimidazole and epoxy resin, benzimidazole and epoxy resin are subjected to addition reaction, so that the adhesive property of epoxy resin is greatly improved, and the finally obtained modified organic silicon adhesive has excellent adhesive property and high heat resistance.
Preferably, in the modified silicone adhesive provided by the embodiment of the present invention, the added epoxy resin compound is a glycidyl ether epoxy resin, a glycidyl ester epoxy resin, a glycidyl amine epoxy resin, a linear aliphatic epoxy resin, or an alicyclic epoxy resin. Wherein, the glycidyl ether epoxy resin and the glycidyl ester epoxy resin have the following characteristics: the viscosity is low, and the application manufacturability is good; the reaction activity is high; the adhesive force is higher than that of the general epoxy resin, and the mechanical property of a condensate is good; the electrical insulation property is good; the weather resistance is good, the ultra-low temperature resistance is good, and the bonding strength is still higher than that of other types of epoxy resin under the ultra-low temperature condition. The glycidyl amine epoxy resin has excellent adhesion and heat resistance. The alicyclic epoxy resin has the characteristics of higher compression and tensile strength, good mechanical property under the high-temperature condition for a long time, and better arc resistance, ultraviolet light aging resistance and weather resistance.
Further, in the modified silicone adhesive provided by the embodiment of the invention, the formula of the polyorganosiloxane is shown in the specification
In the formula: r1Is C1-10Saturated alkanyl radical, Y being C1-5Alkylene, m is an integer, m is not less than 10, n is 0 or 1.
Further preferably, in the modified silicone adhesive provided by the embodiment of the present invention, the toughening agent is carboxyl liquid nitrile rubber, polysulfide rubber, liquid silicone rubber, polyether, polysulfone, nano calcium carbonate, or nano titanium dioxide; the platinum catalyst is a tetramethyldivinyl disiloxane chloroplatinic acid complex; the curing agent is diamino diphenyl sulfone.
The embodiment of the invention also provides a preparation method of the modified organic silicon adhesive, which comprises the following steps: weighing the following components in parts by weight: 15-20 parts of amine compound, 20-25 parts of epoxy resin compound, 20-30 parts of polysiloxane, 2-4 parts of toughening agent and 0.001-0.005 part of platinum catalyst, adding the components into a reaction device under the protection of inert gas, stirring, adding 1-2 parts of curing agent, heating to 30-60 ℃, continuing stirring for 20-30 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 20-40 ℃ for 10-30 minutes to obtain the modified organic silicon adhesive.
Detailed Description
The following describes a method for producing the silicone adhesive of the present invention by way of production examples (in each of the following examples, each raw material is 1 g by mass part).
Example 1
Weighing 16 parts of benzimidazole, 23 parts of epoxy resin compound, namely, phenol type epoxy resin and polysiloxane
25 parts of toughening agent polysulfide rubber, 3 parts of platinum catalyst platinic chloride tetramethyl divinyl disiloxane complex, 0.002 part of platinum catalyst, adding into a reaction device under the protection of inert gas, stirring, adding curing agent diaminodiphenyl sulfone 1.6 parts, heating to 40 ℃, continuing stirring for 20 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 30 ℃ for 10 minutes to obtain the organic silicon adhesive.
Example 2
Weighing 16 parts of benzimidazole, 21 parts of epoxy resin compound bisphenol A type epoxy resin and polysiloxane
25 parts of toughening agent polysulfide rubber, 3 parts of platinum catalyst platinic chloride tetramethyl divinyl disiloxane complex, 0.002 part of platinum catalyst, adding into a reaction device under the protection of inert gas, stirring, adding 1.5 parts of curing agent diaminodiphenyl sulfone, heating to 40 ℃, continuing stirring for 20 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 30 ℃ for 10 minutes to obtain the organic silicon adhesive.
Example 3
Weighing 16 parts of benzimidazole, 23 parts of epoxy resin compound, namely, phenol type epoxy resin and polysiloxane
25 parts of toughening agent liquid silicone rubber, 3 parts of platinum catalyst tetramethyldivinyl disiloxane chloroplatinic acid complex, adding into a reaction device under the protection of inert gas, stirring, adding 1.7 parts of curing agent diaminodiphenyl sulfone, heating to 40 ℃, continuing stirring for 20 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 30 ℃ for 10 minutes to obtain the organic silicon adhesive.
Example 4
Weighing 18 parts of benzimidazole, 20 parts of epoxy resin compound alkene bisphenol F type epoxy resin and polysiloxane
20 parts of toughening agent carboxyl liquid nitrile rubber, 3 parts of platinum catalyst chloroplatinic acid tetramethyl divinyl disiloxane complex, adding into a reaction device under the protection of inert gas, stirring, adding curing agent diaminodiphenyl sulfone 1.0 part, heating to 40 ℃, continuing stirring for 25 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 20 ℃ for 15 minutes to obtain the organic silicon adhesive.
Example 5
Weighing 18 parts of benzimidazole, 20 parts of epoxy resin compound, namely benzenediol epoxy resin and polysiloxane
20 parts of toughening agent carboxyl liquid nitrile rubber, 3 parts of platinum catalyst chloroplatinic acid tetramethyl divinyl disiloxane complex, adding into a reaction device under the protection of inert gas, stirring, adding curing agent diaminodiphenyl sulfone 1.5 parts, heating to 40 ℃, continuing stirring for 25 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 20 ℃ for 15 minutes to obtain the organic silicon adhesive.
Example 6
Weighing 18 parts of benzimidazole, 20 parts of epoxy resin compound alkene bisphenol F type epoxy resin and polyorganosiloxane
20 parts of toughening agent polysulfide rubber, 3 parts of platinum catalyst platinic chloride tetramethyl divinyl disiloxane complex, 0.003 part of platinum catalyst, adding into a reaction device under the protection of inert gas, stirring, adding 1.7 parts of curing agent diaminodiphenyl sulfone, heating to 40 ℃, continuing stirring for 25 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 20 ℃ for 15 minutes to obtain the organic silicon adhesive.
Example 7
Weighing 17 parts of benzimidazole, 23 parts of epoxy resin compound bisphenol A type epoxy resin and polysiloxane
29 parts of toughening agent polysulfide rubber, 3 parts of platinum catalyst, and 0.003 part of platinum catalyst, adding into a reaction device under the protection of inert gas, stirring, adding 1.3 parts of curing agent diaminodiphenyl sulfone, heating to 30 ℃, continuing stirring for 30 minutes, cooling to room temperature to obtain colorless transparent liquid, removing bubbles under reduced pressure, heating for curing and heating at 30 ℃ for 10 minutes to obtain the organic silicon adhesive.
Example 8
Weighing 17 parts of benzimidazole, 23 parts of epoxy resin compound, namely trihydroxyphenyl methane type epoxy resin and polysiloxane
29 parts of toughening agent carboxyl liquid nitrile rubber, 3 parts of platinum catalyst chloroplatinic acid tetramethyl divinyl disiloxane complex, adding into a reaction device under the protection of inert gas, stirring, adding curing agent diaminodiphenyl sulfone 1.8 parts, heating to 30 ℃, continuing stirring for 30 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 30 ℃ for 10 minutes to obtain the organic silicon adhesive.
Example 9
Weighing 17 parts of benzimidazole, 23 parts of epoxy resin compound tetraphenolethane type epoxy resin and polyorganosiloxane
29 parts of toughening agent carboxyl liquid nitrile rubber, 3 parts of platinum catalyst chloroplatinic acid tetramethyl divinyl disiloxane complex, adding into a reaction device under the protection of inert gas, stirring, adding curing agent diaminodiphenyl sulfone 1.9 parts, heating to 30 ℃, continuing stirring for 30 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 30 ℃ for 10 minutes to obtain the organic silicon adhesive.
Comparative example 1 (without amine compound)
Weighing 23 parts of epoxy resin compound tetraphenolethane type epoxy resin and polyorganosiloxane
29 parts of toughening agent carboxyl liquid nitrile rubber, 3 parts of platinum catalyst chloroplatinic acid tetramethyl divinyl disiloxane complex, adding into a reaction device under the protection of inert gas, stirring, adding curing agent diaminodiphenyl sulfone 1.9 parts, heating to 30 ℃, continuing stirring for 30 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 30 ℃ for 10 minutes to obtain the organic silicon adhesive.
Comparative example 2 (without epoxy resin compound)
Weighing 17 parts of benzimidazole and polysiloxane
29 parts of toughening agent carboxyl liquid nitrile rubber, 3 parts of platinum catalyst chloroplatinic acid tetramethyl divinyl disiloxane complex, adding into a reaction device under the protection of inert gas, stirring, adding curing agent diaminodiphenyl sulfone 1.9 parts, heating to 30 ℃, continuing stirring for 30 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 30 ℃ for 10 minutes to obtain the organic silicon adhesive.
Comparative example 3 (composition of amine Compound 5 parts)
Weighing 5 parts of benzimidazole, 23 parts of epoxy resin compound tetraphenolethane type epoxy resin and polyorganosiloxane
29 parts of toughening agent carboxyl liquid nitrile rubber, 3 parts of platinum catalyst chloroplatinic acid tetramethyl divinyl disiloxane complex, adding into a reaction device under the protection of inert gas, stirring, adding curing agent diaminodiphenyl sulfone 1.9 parts, heating to 30 ℃, continuing stirring for 30 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 30 ℃ for 10 minutes to obtain the organic silicon adhesive.
Comparative example 4 (composition of amine Compound 35 parts)
Weighing 35 parts of benzimidazole, 23 parts of epoxy resin compound tetraphenolethane type epoxy resin and polyorganosiloxane
29 parts of toughening agent carboxyl liquid nitrile rubber, 3 parts of platinum catalyst chloroplatinic acid tetramethyl divinyl disiloxane complex, adding into a reaction device under the protection of inert gas, stirring, adding curing agent diaminodiphenyl sulfone 1.9 parts, heating to 30 ℃, continuing stirring for 30 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles,heating, curing and heating for 10 minutes at the temperature of 30 ℃ to obtain the organic silicon adhesive.
Comparative performance test example: performance testing of cured modified Silicone adhesives
Determination of adhesive Strength
And (3) decompressing and removing bubbles from the colorless transparent liquid obtained in each embodiment, coating a small amount of the colorless transparent liquid on glass plates with the length of 10cm, the width of 5cm and the thickness of 2mm respectively, wherein the thickness of the coated organic silicon adhesive is 0.5mm, overlapping the other glass plates with the same size, heating to 30 ℃, taking out after 20 minutes, cooling to room temperature for curing, and testing by a tensile machine. The test results are shown in table 1 below:
TABLE 1 determination of adhesive Strength of modified Silicone Adhesives after curing
High temperature resistance test
And (3) decompressing the colorless transparent liquid obtained in the embodiment example to remove bubbles, heating to 30 ℃, taking out after 20 minutes, cooling to room temperature for curing, baking at the high temperature of 100-300 ℃ for 30 minutes, and measuring the temperature resistance of the organic silicon adhesive. The results are shown in table 2 below:
TABLE 2 high temperature resistance test of cured modified Silicone adhesive
Claims (7)
1. The modified organic silicon adhesive is characterized by comprising the following components in parts by weight:
15-20 parts of amine compounds;
20-25 parts of epoxy resin compounds;
20-30 parts of polysiloxane;
2-4 parts of a toughening agent;
0.001-0.005 part of platinum catalyst;
1-2 parts of a curing agent;
the amine compound is benzimidazole.
2. The modified silicone adhesive of claim 1, wherein the epoxy resin compound is a glycidyl ether epoxy resin, a glycidyl ester epoxy resin, a glycidyl amine epoxy resin, a linear aliphatic epoxy resin, or an alicyclic epoxy resin.
3. The modified silicone adhesive of claim 1, wherein the polyorganosiloxane has the formula
In the formula: r1Is C1-10Saturated alkanyl radical, Y being C1-5Alkylene, m is an integer, m is not less than 10, n is 0 or 1.
4. The modified silicone adhesive of claim 1, wherein the toughening agent is a carboxyl liquid nitrile rubber, a polysulfide rubber, a liquid silicone rubber, a polyether, a polysulfone, a nano calcium carbonate, or a nano titanium dioxide.
5. The modified silicone adhesive of claim 1 wherein the platinum catalyst is a tetramethyldivinyldisiloxane chloroplatinate complex.
6. The modified silicone adhesive of claim 1 wherein the curing agent is diaminodiphenyl sulfone.
7. The method for preparing the modified silicone adhesive according to claim 1, comprising the steps of: weighing the following components in parts by weight: 15-20 parts of amine compound, 20-25 parts of epoxy resin compound, 20-30 parts of polysiloxane, 2-4 parts of toughening agent and 0.001-0.005 part of platinum catalyst, adding the components into a reaction device under the protection of inert gas, stirring, adding 1-2 parts of curing agent, heating to 30-60 ℃, continuing stirring for 20-30 minutes, cooling to room temperature to obtain colorless transparent liquid, decompressing to remove bubbles, heating, curing and heating at 20-40 ℃ for 10-30 minutes to obtain the modified organic silicon adhesive.
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| CN107686717A (en) * | 2017-09-05 | 2018-02-13 | 复旦大学 | A kind of preparation method of high-temperature resistant silicone adhesive |
| CN107722892A (en) * | 2017-09-05 | 2018-02-23 | 复旦大学 | It is a kind of can the organosilicon adhesive sprawled of high thickness and preparation method thereof |
| CN107652943B (en) * | 2017-09-05 | 2020-12-22 | 复旦大学 | Ultraviolet-light-resistant high-temperature-resistant and low-temperature-resistant organic silicon adhesive and preparation method thereof |
| CN110511723B (en) * | 2019-08-23 | 2021-04-02 | 复旦大学 | Liquid crystal display device bonded organic silicon adhesive and preparation method thereof |
| CN110484200A (en) * | 2019-09-11 | 2019-11-22 | 丁爱顺 | A kind of the macromolecule organic silicon adhesive and preparation method thereof |
| CN116769438A (en) * | 2023-07-31 | 2023-09-19 | 苏州添易朗科技有限公司 | Preparation method and application of organic silicon glue |
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