CN111662674A - High-temperature-resistant pressure-sensitive adhesive and preparation method thereof - Google Patents
High-temperature-resistant pressure-sensitive adhesive and preparation method thereof Download PDFInfo
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- CN111662674A CN111662674A CN202010695247.5A CN202010695247A CN111662674A CN 111662674 A CN111662674 A CN 111662674A CN 202010695247 A CN202010695247 A CN 202010695247A CN 111662674 A CN111662674 A CN 111662674A
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
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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
-
- 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
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a high-temperature-resistant pressure-sensitive adhesive and a preparation method thereof, wherein the high-temperature-resistant pressure-sensitive adhesive comprises the following raw materials in parts by weight: 100 parts of organic silicon modified polyurethane acrylic prepolymer, 10-15 parts of tackifying resin, 3-5 parts of cross-linking agent and 50-200 parts of solvent, wherein the organic silicon modified polyurethane acrylic prepolymer comprises the following raw materials in parts by weight: 5-20 parts of hydroxyl-containing acrylate, 25-30 parts of toluene diisocyanate, 10-15 parts of vinyl silicone oil, 0.05-0.1 part of dibutyltin dilaurate, 0-0.01 part of 2, 2-dimethylolpropionic acid, 0.05-0.1 part of hydroquinone and a plurality of diluents. The high-temperature-resistant pressure-sensitive adhesive has high-temperature resistance and peel strength.
Description
Technical Field
The invention relates to the technical field of electrical consumables, in particular to a high-temperature-resistant pressure-sensitive adhesive and a preparation method thereof.
Background
With the rapid development of economy, the adhesive tape is completely integrated into various industries and daily life of people. A special type of adhesive tape is made by applying a special adhesive (pressure sensitive adhesive) to a tape-like substrate. Pressure-sensitive adhesives are the most important components of pressure-sensitive adhesive tapes, and serve to impart pressure-sensitive adhesive properties to the tapes. Under the action of small pressure, the pressure-sensitive adhesive can form firm adhesion, and the adhesion formed between the surfaces of two objects is mainly Van der Waals force, so that the structure of the adhesion surface is not damaged after the adhesion surface is formed. The pressure-sensitive adhesive has the characteristics of easy adhesion, difficult uncovering, no damage after peeling, no dry and solid adhesive layer in a long time, simple and convenient use and the like, and is widely applied to various fields of industry, daily use, medical use and the like.
The pressure-sensitive adhesive commonly used at present is acrylate pressure-sensitive adhesive, has the advantages of excellent pressure sensitivity, adhesion, oxidation resistance, light resistance, aging resistance and the like, and is widely applied in various industries. The acrylate pressure-sensitive adhesive has better high temperature resistance than natural rubber pressure-sensitive adhesive and synthetic rubber sub-sensitive adhesive, but in some special building and industrial fields, the temperature resistance of the high temperature resistant adhesive tape which is usually required is usually between 120 ℃ and 260 ℃, and exceeds 500 ℃ in a short time. The ability to provide pressure sensitive adhesives with high peel strength, high holding power, high adhesion, and high performance over a wide range of use temperatures has been a constant endeavor addressed by those skilled in the art.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a high-temperature-resistant pressure-sensitive adhesive.
In order to achieve the purpose, the invention adopts the technical scheme that: the high-temperature-resistant pressure-sensitive adhesive comprises the following raw materials in parts by weight: 100 parts of organic silicon modified polyurethane acrylic prepolymer, 10-15 parts of tackifying resin, 3-5 parts of cross-linking agent and 50-200 parts of solvent, wherein the organic silicon modified polyurethane acrylic prepolymer comprises the following raw materials in parts by weight: 5-20 parts of hydroxyl-containing acrylate, 25-30 parts of toluene diisocyanate, 10-15 parts of vinyl silicone oil, 0.05-0.1 part of dibutyltin dilaurate, 0-0.01 part of 2, 2-dimethylolpropionic acid, 0.05-0.1 part of hydroquinone and a plurality of diluents.
Preferably, the organosilicon modified polyurethane pre-acrylic polymer is prepared by the following steps:
weighing the raw material components in parts by weight, adding toluene diisocyanate and 1/2 vinyl silicone oil into a reaction kettle, then adding dibutyltin dilaurate, heating to 80-90 ℃, carrying out ultrasonic stirring reaction for 2-3 hours, then cooling to room temperature, then adding hydroxyl-containing acrylate, hydroquinone, 2-dimethylolpropionic acid and the rest vinyl silicone oil into the reaction kettle, heating to 65-70 ℃, reacting for 1-3 hours, cooling to room temperature, then adding a diluent for dilution, carrying out low-speed centrifugal treatment in the dilution process, wherein the centrifugal rotation speed is 500-600r/min, and completely diluting.
As a specific embodiment, the crosslinking agent is a polyisocyanate-based crosslinking agent.
As a specific embodiment, the tackifying resin is a mixture of terpene phenol resin and rosin resin, and the addition amount of the terpene phenol resin and the rosin resin is 1: 0.5-1.
As a specific embodiment, toluene or ethyl acetate is used as the solvent and the diluent.
The invention also aims to provide a method for preparing the high-temperature-resistant pressure-sensitive adhesive, which comprises the following specific steps: mixing tackifying resin and solvent, centrifugally stirring to dissolve tackifying resin, adding organosilicon modified polyurethane acrylate prepolymer and cross-linking agent into a mixed system, stirring at low speed for 5-10 min, vacuumizing to remove solvent, uniformly coating on a substrate, and heating to 80-100 ℃ for curing.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages: according to the high-temperature-resistant pressure-sensitive adhesive, the organic silicon modified polyurethane acrylic prepolymer is prepared by mutually matching hydroxyl-containing acrylate, toluene diisocyanate, vinyl silicone oil, 2-dimethylolpropionic acid and the like, and then tackifying resin and the like are added to obtain the pressure-sensitive adhesive, so that the high-temperature resistance of the pressure-sensitive adhesive is improved, and the pressure-sensitive adhesive has good initial adhesion and peel strength.
Detailed Description
The technical solution of the present invention is further illustrated below with reference to specific examples.
Example 1
The embodiment provides a high-temperature-resistant pressure-sensitive adhesive which comprises the following raw materials in parts by weight: 100 parts of organic silicon modified polyurethane acrylic prepolymer, 10 parts of tackifying resin, 4 parts of polyisocyanate crosslinking agent and 100 parts of toluene. The tackifying resin is prepared by mixing terpene phenol resin and rosin resin according to the mass ratio of 1:1, and the organic silicon modified polyurethane acrylic prepolymer is prepared from the components in the table 1.
TABLE 1
| Example 1 | Example 2 | Example 3 | Example 4 | Comparative example 1 | Comparative example 2 | |
| Hydroxyl-containing acrylic esters | 5 | 10 | 15 | 20 | 2 | 22 |
| Toluene diisocyanate | 25 | 26 | 30 | 28 | 32 | 20 |
| Vinyl silicone oil | 12 | 10 | 13 | 15 | 17 | 8 |
| Dibutyl tin dilaurate | 0.07 | 0.05 | 0.1 | 0.08 | 0.05 | 0.01 |
| 2, 2-dimethylolpropionic acid | 0 | 0.01 | 0.01 | 0 | 0 | 0 |
| Hydroquinone | 0.05 | 0.07 | 0.1 | 0.08 | 0.1 | 0.1 |
| Toluene | 30 | 40 | 40 | 50 | 20 | 40 |
The preparation method comprises the following steps:
1) preparing an organic silicon modified polyurethane acrylic prepolymer, weighing raw material components according to the weight parts, adding toluene diisocyanate and 1/2 vinyl silicone oil into a reaction kettle, adding dibutyltin dilaurate, heating to 80-90 ℃, carrying out ultrasonic stirring reaction for 2-3 hours, cooling to room temperature, adding hydroxyl-containing acrylate, hydroquinone, 2-dimethylolpropionic acid and the rest vinyl silicone oil into the reaction kettle, heating to 65-70 ℃, carrying out reaction for 1-3 hours, cooling to room temperature, adding a diluent for dilution, carrying out low-speed centrifugal treatment in the dilution process, wherein the centrifugal rotation speed is 500-600r/min, and completely diluting;
2) preparing pressure-sensitive adhesive, mixing tackifying resin and solvent, centrifugally stirring to dissolve tackifying resin, adding organosilicon modified polyurethane acrylate prepolymer and cross-linking agent into a mixed system, stirring at low speed for 5-10 min, vacuumizing to remove solvent, uniformly coating on a base material, heating to 80-100 ℃ and curing. The pressure-sensitive adhesives obtained in examples 1 to 4 and comparative example were coated to a thickness of 50um and tested using 50um aluminum foil as a backing material, and the test data are shown in table 2.
The relevant test methods are as follows:
1) initial tack test: selecting a 6032 adhesive tape retention tester (MIDEL KJ-6032, detection instrument Co., Ltd. of Dongguan), testing according to GB/T4852-2002, and using a ball number to represent the initial adhesion;
2) viscosity retention: selecting a temperature type adhesive tape retention force testing machine (MIDEL KJ-6012, Kokai detection instrument Co., Ltd. of Dongguan), testing according to GB/T4851-2014, and calculating the permanent adhesive force according to the time of adhesive tape shearing damage and falling;
3)180 ° peel strength: selecting a computer type tensile testing machine (MIDEL KJ-1065A, detection instrument Co., Ltd. of Dongguan city), and testing according to GB/T2792-2014;
4) high-temperature permanent adhesion: a temperature-type adhesive tape retention force tester (MIDEL KJ-6012, manufactured by inspection instruments Co., Ltd. of Dongguan) was selected and a permanent adhesion force test was carried out at 100 ℃ to evaluate the high temperature resistance of the pressure-sensitive adhesive tape.
TABLE 2
From table 2, it can be seen that, under the condition that other components are the same, the content of each component in the silicone modified polyurethane acrylic prepolymer is adjusted, and various performance indexes of the pressure-sensitive adhesive prepared by the pressure-sensitive adhesive are different, and particularly, the performance of the pressure-sensitive adhesive is greatly influenced by the proportion of the hydroxyl-containing acrylate, the toluene diisocyanate and the vinyl silicone oil.
Example 2
The embodiment provides a high-temperature-resistant pressure-sensitive adhesive which comprises the following raw materials in parts by weight: the contents of the components are shown in table 3.
The organic silicon modified polyurethane acrylic prepolymer is prepared from the following raw materials: 15 parts of hydroxyl-containing acrylate, 30 parts of toluene diisocyanate, 13 parts of vinyl silicone oil, 0.1 part of dibutyltin dilaurate, 0.01 part of 2, 2-dimethylolpropionic acid, 0.1 part of hydroquinone and 40 parts of ethyl acetate.
TABLE 3
The pressure-sensitive adhesives obtained in examples 5 to 7 and comparative example were coated to a thickness of 50um and tested using 50um aluminum foil as a backing material, and the test data are shown in table 4.
TABLE 4
From Table 4, it can be seen that, under the condition of the same content of other components, increasing the content of tackifying resin is beneficial to increase the initial tack, the peeling force and the permanent tack, and meanwhile, the blending ratio of terpene phenol resin and rosin resin leads to the decrease of various performances of the pressure-sensitive adhesive if the content of rosin resin exceeds the content of terpene phenol resin.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (6)
1. The high-temperature-resistant pressure-sensitive adhesive is characterized by comprising the following raw materials in parts by weight: 100 parts of organic silicon modified polyurethane acrylic prepolymer, 10-15 parts of tackifying resin, 3-5 parts of cross-linking agent and 50-200 parts of solvent, wherein the organic silicon modified polyurethane acrylic prepolymer comprises the following raw materials in parts by weight: 5-20 parts of hydroxyl-containing acrylate, 25-30 parts of toluene diisocyanate, 10-15 parts of vinyl silicone oil, 0.05-0.1 part of dibutyltin dilaurate, 0-0.01 part of 2, 2-dimethylolpropionic acid, 0.05-0.1 part of hydroquinone and a plurality of diluents.
2. The high-temperature-resistant pressure-sensitive adhesive according to claim 1, wherein the silicone-modified polyurethane pre-acrylic polymer is prepared by the following steps:
weighing the raw material components in parts by weight, adding toluene diisocyanate and 1/2 vinyl silicone oil into a reaction kettle, then adding dibutyltin dilaurate, heating to 80-90 ℃, carrying out ultrasonic stirring reaction for 2-3 hours, then cooling to room temperature, then adding hydroxyl-containing acrylate, hydroquinone, 2-dimethylolpropionic acid and the rest vinyl silicone oil into the reaction kettle, heating to 65-70 ℃, reacting for 1-3 hours, cooling to room temperature, then adding a diluent for dilution, carrying out low-speed centrifugal treatment in the dilution process, wherein the centrifugal rotation speed is 500-600r/min, and completely diluting.
3. The high temperature-resistant pressure-sensitive adhesive of claim 1, wherein the crosslinking agent is a polyisocyanate-based crosslinking agent.
4. The high-temperature-resistant pressure-sensitive adhesive as claimed in claim 1, wherein the tackifying resin is a mixture of terpene phenol resin and rosin resin, and the dosage of the terpene phenol resin and the rosin resin is 1: 0.5-1.
5. The high temperature-resistant pressure-sensitive adhesive of claim 1, wherein the solvent and the diluent are toluene or ethyl acetate.
6. A method for preparing the high-temperature-resistant pressure-sensitive adhesive according to any one of claims 1 to 5, which comprises the following specific steps: mixing tackifying resin and solvent, centrifugally stirring to dissolve tackifying resin, adding organosilicon modified polyurethane acrylate prepolymer and cross-linking agent into a mixed system, stirring at low speed for 5-10 min, vacuumizing to remove solvent, uniformly coating on a substrate, and heating to 80-100 ℃ for curing.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202010695247.5A CN111662674A (en) | 2020-07-19 | 2020-07-19 | High-temperature-resistant pressure-sensitive adhesive and preparation method thereof |
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| CN202010695247.5A CN111662674A (en) | 2020-07-19 | 2020-07-19 | High-temperature-resistant pressure-sensitive adhesive and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114231162A (en) * | 2021-11-12 | 2022-03-25 | 广东腐蚀科学与技术创新研究院 | Organic silicon modified polyurethane acrylate ultraviolet light and moisture dual-curing three-proofing paint and preparation method thereof |
| CN117165242A (en) * | 2023-09-19 | 2023-12-05 | 佛山市极威新材料有限公司 | High Wen Baofu resistant adhesive and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516907A (en) * | 2011-12-13 | 2012-06-27 | 烟台德邦电子材料有限公司 | Preparation method of ultraviolet-curable organosilicone-modified pressure-sensitive adhesive |
| CN102911633A (en) * | 2012-10-18 | 2013-02-06 | 四川大学 | Branched-structure polyurethane-silicious polyacrylate hot melt adhesive and preparation method thereof |
-
2020
- 2020-07-19 CN CN202010695247.5A patent/CN111662674A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516907A (en) * | 2011-12-13 | 2012-06-27 | 烟台德邦电子材料有限公司 | Preparation method of ultraviolet-curable organosilicone-modified pressure-sensitive adhesive |
| CN102911633A (en) * | 2012-10-18 | 2013-02-06 | 四川大学 | Branched-structure polyurethane-silicious polyacrylate hot melt adhesive and preparation method thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114231162A (en) * | 2021-11-12 | 2022-03-25 | 广东腐蚀科学与技术创新研究院 | Organic silicon modified polyurethane acrylate ultraviolet light and moisture dual-curing three-proofing paint and preparation method thereof |
| CN117165242A (en) * | 2023-09-19 | 2023-12-05 | 佛山市极威新材料有限公司 | High Wen Baofu resistant adhesive and preparation method and application thereof |
| CN117165242B (en) * | 2023-09-19 | 2024-05-14 | 佛山市极威新材料有限公司 | High-resistant Wen Baofu adhesive and preparation method and application thereof |
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