CN114621451B - Pure polyester resin modified epoxy resin and preparation method and application thereof - Google Patents
Pure polyester resin modified epoxy resin and preparation method and application thereof Download PDFInfo
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- CN114621451B CN114621451B CN202210334122.9A CN202210334122A CN114621451B CN 114621451 B CN114621451 B CN 114621451B CN 202210334122 A CN202210334122 A CN 202210334122A CN 114621451 B CN114621451 B CN 114621451B
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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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
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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
- C09J187/00—Adhesives based on unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
- C09J187/005—Block or graft polymers not provided for in groups C09J101/00 - C09J185/04
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/35—Heat-activated
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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
- C08G2170/00—Compositions for adhesives
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/304—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being heat-activatable, i.e. not tacky at temperatures inferior to 30°C
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
Abstract
The invention discloses a pure polyester resin modified epoxy resin, which is prepared by the following steps: mixing the polyester with high acid value and the mixed solvent, heating to dissolve the polyester completely, adding the epoxy resin and the catalyst, and reacting at 100-120 ℃ until the acid value of the reaction solution is less than or equal to 5mg KOH/g. The pure polyester resin modified epoxy resin has the characteristics of polyester and epoxy resin, can be used as a coating to be coated on a film, and the obtained film belongs to a laminating adhesive film, has no tackiness on the surface at room temperature, can be stored in a coiled manner, has a certain tackiness under the heating condition, can be pressed on the surface of an object, and can be peeled off to solidify the coating. The invention has simple operation process, low requirement on process conditions, lower production cost, environmental friendliness and convenient mass production.
Description
Technical Field
The invention relates to a pure polyester resin modified epoxy resin, a preparation method thereof and application thereof in preparation of a laminating adhesive film, and application thereof in serving as a hard adhesive film coating, belonging to the technical field of coatings.
Background
The epoxy resin is a high-performance thermosetting polymer material, has excellent technological properties, adhesive properties, wear resistance, mechanical properties, electrical insulation, chemical stability, high and low temperature resistance and the like, and is attractive worldwide due to the advantages of low shrinkage, good adhesion to various base materials, low cost and the like. The epoxy resin can be made into surface coating, adhesive, laminated board, semiconductor package and electric equipment, and is widely applied in various fields of national economy. The polyester with high acid value contains a large amount of carboxyl groups, which are subjected to ring-opening reaction with epoxy groups in the epoxy resin, and the polyester is introduced into the epoxy resin, so that the defect of insufficient toughness of the epoxy resin can be overcome to a certain extent.
The Chinese patent No. 109627726B discloses a pure resin type polyester epoxy environment-friendly impregnating resin and a preparation method thereof, wherein acrylic acid modified epoxy resin is used as a raw material, and the acrylic acid modified epoxy resin has the dual performance advantages of unsaturated resin and epoxy resin, can generate crosslinking copolymerization reaction with polyester acrylate resin, and can also perform epoxy curing crosslinking reaction by itself, thereby being beneficial to improving the copolymerization degree and crosslinking density of a resin system and leading the impregnating resin to have excellent mechanical bonding performance, heat resistance and dielectric property. The Chinese patent application CN 112778529A discloses a preparation method of polyester modified epoxy resin for coiled material primer, which is characterized in that a linear polyester intermediate with a certain flexible chain segment is synthesized, carboxyl or hydroxyl in the polyester intermediate is subjected to ring opening reaction with epoxy resin under the action of a catalyst to obtain polyester modified epoxy resin, and a paint film obtained by crosslinking the polyester modified epoxy resin and amino resin has good flexibility, so that the defect of the epoxy resin primer is overcome. However, the two technical schemes are complicated to operate and inconvenient to store as impregnating resin or coiled material primer, so that the research of the environment-friendly pressure-sensitive adhesive film coating with simple operation has very important significance.
Disclosure of Invention
Aiming at the prior art, the invention provides a pure polyester resin modified epoxy resin, a preparation method thereof and application thereof in preparation of a laminating adhesive film and application thereof in serving as a hard adhesive film coating. The modified epoxy resin is prepared by utilizing the ring-opening reaction of carboxyl in the polyester and epoxy groups in the epoxy resin, so that the modified epoxy resin has the characteristics of both the polyester and the epoxy resin. The pure polyester resin modified epoxy resin is used as a coating to be coated on a film, the obtained film material belongs to a laminating adhesive film, the surface of the film material is not sticky at room temperature, the film material can be stored in a coiled manner, and the adhesive film has certain sticky property under the heating condition and can be pressed and adhered on the surface of an object.
The invention is realized by the following technical scheme:
a preparation method of pure polyester resin modified epoxy resin comprises the following steps: mixing high acid value polyester with a mixed solvent, heating to dissolve the polyester completely, adding epoxy resin and a catalyst, and reacting at 100-120 ℃ until the acid value of the reaction solution is less than or equal to 5mg KOH/g, thus obtaining pure polyester resin modified epoxy resin;
the high acid value polyester refers to polyester with an acid value of 100-200 mg KOH/g;
the mixed solvent is any mixture of more than two of dimethylbenzene, n-butanol, n-heptane, isopropanol, dimethyl carbonate, ethyl acetate and toluene, preferably the mixture of dimethylbenzene and n-butanol;
the dosage proportion relation of the high acid value polyester, the mixed solvent and the epoxy resin is as follows: 25-40 parts of high acid value polyester, 40-50 parts of mixed solvent and 20-35 parts of epoxy resin.
Further, the epoxy resin is selected from any one or a combination of more than two of E-44, E-51, E-54 and AG-80.
Further, the catalyst is selected from triphenylphosphine.
Further, the catalyst is used in an amount of 0.01 to 0.06 percent of the total weight of reactants (the total weight of the high acid value polyester and the epoxy resin).
Further, the dissolution temperature of the polyester is controlled to be 60-80 ℃.
Further, the reaction is divided into two steps, namely, the following steps: heating to 100-115 ℃ for the first time, wherein the reaction time is 1-1.5 h; and heating to 110-120 ℃ for the second time, wherein the reaction time is 2-4 h.
The pure polyester resin modified epoxy resin prepared by the method has the characteristics of polyester and epoxy resin and can be used as a coating to be coated on a film; in specific application, a film with strippable property is selected, the modified epoxy resin film is subjected to heating by a wet film preparation device to remove part of solvent, and the film with a film coating is prepared after standing for 10-20 min at room temperature, the obtained film belongs to a laminating adhesive film, the surface of the film is not sticky at room temperature, the film can be stored in a coiled manner, the adhesive film has certain sticky property under the heating condition, the film can be pressed on the surface of an object, and the film is stripped, so that the coating is solidified.
Further, the temperature of the solvent is 80-100 ℃ and the time is 20-40 min.
The modified epoxy resin is prepared by the ring-opening reaction of carboxyl in polyester and epoxy groups in epoxy resin; and selecting a strippable film, forming a film material with a film coating by using the resin film, wherein the surface of the film material is not sticky at room temperature, and the prepared film material can be stored in a roll. And (3) a heat source is given, the film material can be attached to the surface of an object in a pressing mode, and the film is peeled off to solidify the coating. The preparation method and the application of the invention have the advantages of simple operation process, low requirements on process conditions, low production cost, environmental friendliness and convenience for mass production.
Detailed Description
The invention is further illustrated below with reference to examples. However, the scope of the present invention is not limited to the following examples. Those skilled in the art will appreciate that various changes and modifications can be made to the invention without departing from the spirit and scope thereof.
The instruments, reagents, materials, etc. used in the examples described below are conventional instruments, reagents, materials, etc. known in the art, and are commercially available. The experimental methods, detection methods, and the like in the examples described below are conventional experimental methods, detection methods, and the like that are known in the prior art unless otherwise specified.
Example 1
(1) 100g of a high acid value polyester (polyester having an acid value of 120mg KOH/g), 83g of xylene and 35g of n-butanol were charged into a reaction vessel, and the reaction temperature was controlled to 80℃to dissolve the polyester. After the polyester is completely dissolved, 77g of epoxy resin E-54 and 0.10g of triphenylphosphine are added, the temperature is raised to 100 ℃ for reaction for 1.5h, the temperature is continuously raised to 120 ℃ for reaction for 3h, the temperature is reduced to 60 ℃ and the mixture is bottled for standby.
(2) Selecting a film with strippable property, heating to remove part of solvent (the temperature is 90 ℃ for 30 min) by using a wet film preparation device to obtain a film material with a film coating, wherein the surface of the film material is not sticky at room temperature. And giving a certain amount of heat to the film, pressing the film on the surface of an object, peeling the film, and curing the coating to form the peelable adhesive film coating with curing performance.
Example 2
(1) 100g of a high acid number polyester (polyester having an acid number of 120mg KOH/g), 92g of xylene and 39g of n-butanol were charged into a reaction vessel, and the reaction temperature was controlled to 80℃to dissolve the polyester. After the polyester has completely dissolved, 96g of epoxy resin E-54 and 0.15g of triphenylphosphine are added. Heating to 110 ℃ for reaction for 1.5h, continuously heating to 120 ℃ for reaction for 3h, cooling to 60 ℃ and bottling for standby.
(2) Selecting a film with strippable property, heating to remove part of solvent (temperature 80 ℃ C., time 40 min) by using a wet film preparation device to obtain a film material with a film coating, wherein the surface of the film material is not sticky at room temperature. And giving a certain amount of heat to the film, pressing the film on the surface of an object, peeling the film, and curing the coating to form the peelable adhesive film coating with curing performance.
Example 3
(1) 100g of a high acid value polyester (polyester having an acid value of 150mg KOH/g), 101g of xylene and 43g of n-butanol were charged into a reaction vessel, and the reaction temperature was controlled to 80℃to dissolve the polyester. After the polyester has completely dissolved, 116g of epoxy E-54 and 0.12g of triphenylphosphine are added. Heating to 110 ℃ for reaction for 1h, continuously heating to 120 ℃ for reaction for 2h, cooling to 60 ℃ and bottling for standby.
(2) Selecting a film with strippable property, heating to remove part of solvent (temperature 100 ℃ C., time 20 min) by using a wet film preparation device to obtain a film material with a film coating, wherein the surface of the film material is not sticky at room temperature. And giving a certain amount of heat to the film, pressing the film on the surface of an object, peeling the film, and curing the coating to form the peelable adhesive film coating with curing performance.
Example 4
(1) 50g of a high acid value polyester (polyester having an acid value of 200mg KOH/g), 82g of xylene and 35g of n-butanol were charged into a reaction vessel, and the reaction temperature was controlled to 80℃to dissolve the polyester. After the polyester has completely dissolved, 125g of epoxy AG-80 and 0.05g of triphenylphosphine are added. Heating to 100deg.C for reaction for 1 hr, continuously heating to 110deg.C for reaction for 2 hr, cooling to 60deg.C, and bottling.
(2) Selecting a film with strippable property, heating to remove part of solvent (temperature 100 ℃ C., time 40 min) by using a wet film preparation device to obtain a film material with a film coating, wherein the surface of the film material is not sticky at room temperature. And giving a certain amount of heat to the film, pressing the film on the surface of an object, peeling the film, and curing the coating to form the peelable adhesive film coating with curing performance.
Example 5
(1) 50g of a high acid number polyester (polyester having an acid number of 120mg KOH/g), 90g of xylene and 39g of n-butanol were charged into a reaction vessel, and the reaction temperature was controlled to 80℃to dissolve the polyester. After the polyester has completely dissolved, 143g of epoxy AG-80 and 0.05g of triphenylphosphine are added. Heating to 100deg.C for reaction for 1 hr, continuously heating to 110deg.C for reaction for 2 hr, cooling to 60deg.C, and bottling.
(2) Selecting a film with strippable property, heating to remove part of solvent (the temperature is 90 ℃ for 40 min) by using a wet film preparation device to obtain a film material with a film coating, wherein the surface of the film material is not sticky at room temperature. And giving a certain amount of heat to the film, pressing the film on the surface of an object, peeling the film, and curing the coating to form the peelable adhesive film coating with curing performance.
The test results are shown in tables 1 to 4. As is clear from tables 1 to 4, the polyester-modified epoxy resin of the present invention has a low acid value, and when applied as a film-pressing coating, it has a high peel strength and a good effect.
TABLE 1 examples 1-5 acid value test results for polyester modified epoxy resins
TABLE 2 Pencil hardness test results for hard film coatings of examples 1-5
| Hardness of pencil | |
| Example 1 | 2HB |
| Example 2 | H |
| Example 3 | 3HB |
| Example 4 | HB |
| Example 5 | 2HB |
Table 3 results of 90 ° peel test of the hard film coatings of examples 1-5
| 90 degree peel strength (N/cm) | |
| Example 1 | 25 |
| Example 2 | 27 |
| Example 3 | 14 |
| Example 4 | 20 |
| Example 5 | 18 |
Table 4 180 ° peel test results for hard film coatings of examples 1-5
| 180 degree peel strength (N/cm) | |
| Example 1 | 28 |
| Example 2 | 30 |
| Example 3 | 17 |
| Example 4 | 22 |
| Example 5 | 21 |
The foregoing examples are provided to fully disclose and describe how to make and use the claimed embodiments by those skilled in the art, and are not intended to limit the scope of the disclosure herein. Modifications that are obvious to a person skilled in the art will be within the scope of the appended claims.
Claims (5)
1. A preparation method of pure polyester resin modified epoxy resin is characterized in that: adding high acid value polyester with an acid value of 100g of 120mg KOH/g, 92g dimethylbenzene and 39g n-butanol into a reaction vessel, and controlling the reaction temperature to be 80 ℃ to dissolve the polyester; after the polyester is completely dissolved, 96g epoxy resin E-54 and 0.15g triphenylphosphine are added, the temperature is raised to 110 ℃ to react 1.5h, the temperature is continuously raised to 120 ℃ to react 3h, and the temperature is reduced to 60 ℃, thus obtaining the polyester.
2. The pure polyester resin modified epoxy resin prepared by the preparation method of claim 1.
3. The use of the pure polyester resin modified epoxy resin of claim 2 in the preparation of conformable adhesive films.
4. A use according to claim 3, characterized in that: in specific application, selecting a film with strippability, coating a pure polyester resin modified epoxy resin film by using a wet film preparation device, heating to remove part of solvent, and standing at room temperature for 10-20 min to obtain a film material with a film coating; the temperature of the solvent removal is 80 ℃ and the time is 40min.
5. The film material with the adhesive film coating is characterized by being prepared by the following steps: selecting a film with strippable property, utilizing a wet film preparation device to coat the pure polyester resin modified epoxy resin film of claim 2, heating to remove part of solvent, and standing for 10-20 min at room temperature to obtain the product.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483525A (en) * | 2013-08-23 | 2014-01-01 | 西北矿冶研究院 | Modified epoxy resin with corrosion resistance and wear resistance and preparation method thereof |
| CN110330871A (en) * | 2019-07-26 | 2019-10-15 | 平原温特实业有限公司 | The application method that epoxy modified polyester resin is synthesized in pre-coated metal coil coating priming paint |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2834346B2 (en) * | 1991-08-13 | 1998-12-09 | 桜宮化学株式会社 | Thermal laminating adhesive for cans |
| US20220306859A1 (en) * | 2019-04-26 | 2022-09-29 | Toagosei Co., Ltd. | Resin composition, bonding film, layered body including resin composition layer, layered body, and electromagnetic wave shielding film |
| CN110343445B (en) * | 2019-07-17 | 2020-12-22 | 中国科学院过程工程研究所 | Powder coating composition and preparation method and application thereof |
| EP3835379A4 (en) * | 2019-08-02 | 2021-11-03 | Kinte Materials Science and Technology Co., Ltd. | Polyester resin composition, powder coating and workpiece |
| CN112778529A (en) * | 2020-12-30 | 2021-05-11 | 万博新材料科技（南通）有限公司 | Preparation method of polyester modified epoxy resin for coil primer |
| CN113801331B (en) * | 2021-09-06 | 2022-06-14 | 华南理工大学 | Waterborne hyperbranched polyester-based epoxy curing agent and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483525A (en) * | 2013-08-23 | 2014-01-01 | 西北矿冶研究院 | Modified epoxy resin with corrosion resistance and wear resistance and preparation method thereof |
| CN110330871A (en) * | 2019-07-26 | 2019-10-15 | 平原温特实业有限公司 | The application method that epoxy modified polyester resin is synthesized in pre-coated metal coil coating priming paint |
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