CN115521737A - Medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive and preparation method thereof - Google Patents
Medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive and preparation method thereof Download PDFInfo
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- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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- C09J133/20—Homopolymers or copolymers of acrylonitrile
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- 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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Abstract
A medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive and a preparation method thereof relate to an acrylate pressure-sensitive adhesive and a preparation method thereof. The invention aims to solve the problem that the existing acrylate pressure-sensitive adhesive has poor medium resistance and high temperature resistance. The medium-resistant high-temperature-resistant acrylate pressure-sensitive adhesive is prepared from 70-90 parts by weight of soft monomer, 5-15 parts by weight of hard monomer, 7-12 parts by weight of functional monomer, 4-10 parts by weight of modified monomer, 5-15 parts by weight of fluorine-containing monomer, 5-20 parts by weight of acrylate rubber solution, 0.5-1.5 parts by weight of initiator, 80-120 parts by weight of solvent, 5-10 parts by weight of polytetrafluoroethylene powder and 0.2-2.5 parts by weight of fluorine-containing cross-linking agent. According to the invention, the medium-resistant high-temperature-resistant acrylate pressure-sensitive adhesive with excellent comprehensive performance is prepared by using the fluorine-containing monomer, the acrylate rubber, the polytetrafluoroethylene powder and the fluorine-containing cross-linking agent and controlling the synthesis steps.
Description
Technical Field
The invention relates to an acrylate pressure-sensitive adhesive and a preparation method thereof.
Background
The acrylate pressure-sensitive adhesive has high bonding strength to various materials, excellent ultraviolet aging resistance, water resistance and storage stability, and is applied to various fields. In order to meet the requirements of corrosion prevention, moisture prevention, protection, stealth and the like of aircrafts in the aviation industry, a large number of protective adhesive tapes or functional adhesive tapes are also used.
Because the pressure-sensitive adhesive used by the common adhesive tape may contact with various media such as aviation kerosene, cooling liquid, hydraulic oil and the like in the manufacturing, maintenance and use processes, the pressure-sensitive adhesive used by the common adhesive tape is easy to dissolve, swell, deform and even fall off, and the flight safety of an airplane is damaged. Meanwhile, due to the complex application environment, the high temperature resistance of the pressure-sensitive adhesive is also required.
In the domestic research on pressure-sensitive adhesives, no report is provided for specially improving the medium resistance of the pressure-sensitive adhesive. The patent US4994538A synthesizes a pressure-sensitive adhesive containing organic silicon acrylate active polymer by using an emulsion polymerization method, and the pressure-sensitive adhesive has better water resistance and gasoline resistance. Patent US 2925174A teaches that the products obtained by copolymerisation of acrylate monomers with acrylic acid or acrylamide have a certain oil resistance. It is stated in US3269994 that increasing the crosslink density of the adhesive layer improves the solvent resistance of the pressure sensitive adhesive.
For the research on the improvement of the high-temperature resistance of the pressure-sensitive adhesive, patents such as CN201910732144.9, CN202110750789.2, and CN202210167947.6 are all related, but the strength of the pressure-sensitive adhesive at high temperature is not tested. Patent CN202210686141.8 provides an acrylate pressure-sensitive adhesive with high and low temperature resistance and high strength and a preparation method thereof, and tests the strength of the pressure-sensitive adhesive at 150 ℃, but the prepared product has no medium resistance.
Disclosure of Invention
The invention aims to solve the problem that the existing acrylate pressure-sensitive adhesive is poor in medium resistance and high temperature resistance, and provides a medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive and a preparation method thereof.
The medium-resistant high-temperature-resistant acrylate pressure-sensitive adhesive is prepared from 70-90 parts by weight of soft monomer, 5-15 parts by weight of hard monomer, 7-12 parts by weight of functional monomer, 4-10 parts by weight of modified monomer, 5-15 parts by weight of fluorine-containing monomer, 5-20 parts by weight of acrylate rubber solution, 0.5-1.5 parts by weight of initiator, 80-120 parts by weight of solvent, 5-10 parts by weight of polytetrafluoroethylene powder and 0.2-2.5 parts by weight of fluorine-containing cross-linking agent;
the preparation method of the fluorine-containing cross-linking agent comprises the following steps:
under the protection of nitrogen, adding diisocyanate and fluorine-containing monohydric alcohol into a reactor, adding a catalyst, and reacting at 70-100 ℃ for 3-7 h to obtain a fluorine-containing cross-linking agent;
the molar ratio of the diisocyanate to the fluorine-containing monohydric alcohol is (5-10): 1;
the catalyst accounts for 0.1-2.0% of the mass of the diisocyanate.
A preparation method of medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive is completed according to the following steps:
1. preparing a fluorine-containing cross-linking agent:
under the protection of nitrogen, adding diisocyanate and fluorine-containing monohydric alcohol into a reactor, adding a catalyst, and reacting at 70-100 ℃ for 3-7 hours to obtain a fluorine-containing cross-linking agent; the molar ratio of the diisocyanate to the fluorine-containing monohydric alcohol is (5-10) to 1; the catalyst accounts for 0.1 to 2.0 percent of the mass of the diisocyanate;
2. weighing 70-90 parts of soft monomer, 5-15 parts of hard monomer, 7-12 parts of functional monomer, 4-10 parts of modified monomer, 5-15 parts of fluorine-containing monomer, 5-20 parts of acrylate rubber solution, 0.5-1.5 parts of initiator, 80-120 parts of solvent, 5-10 parts of polytetrafluoroethylene powder and 0.2-2.5 parts of fluorine-containing cross-linking agent according to parts by weight; dividing an initiator and a solvent into three parts respectively;
3. adding a soft monomer, a hard monomer, a modified monomer, a part of initiator and a part of solvent into a reaction vessel, heating to 75-83 ℃ under the condition of stirring, and reacting for 0.5-1.0 h under the condition of stirring and the temperature of 75-83 ℃;
4. mixing a part of initiator, a part of solvent and fluorine-containing monomer, and dropwise adding the mixed material into the reaction container in the third step at a constant speed within the time range of 1.0-1.5 h;
5. mixing the residual initiator, the residual solvent and the functional monomer, dropwise adding the mixed material into the reaction container in the fourth step at a constant speed within the time range of 0.5-1.5 h, continuing the reaction after the dropwise adding is finished, and stopping when the viscosity is increased to the range of 2500-3000 cp;
6. adding an acrylate rubber solution, polytetrafluoroethylene powder and a fluorine-containing cross-linking agent into the reaction vessel in the fifth step, and dispersing uniformly at a high speed to obtain a glue solution; coating the glue solution on a PET release film by using a 100-600 mu m coater, airing for 0.5-2 h, putting the PET release film into an oven, drying the PET release film for 1-2 h at the temperature of 100-120 ℃, and then transferring the PET release film to an aluminum foil which is anodized by phosphoric acid and has the thickness of 0.03-0.08 mm to obtain the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive.
The principle of the invention is as follows:
the invention takes conventional soft monomers and hard monomers as basic raw materials, takes acrylonitrile and fluorine-containing monomers as medium-resistant monomers, and prepares the acrylate pressure-sensitive adhesive solution with certain medium resistance and heat resistance through synthetic reaction; when the film is prepared, the high molecular weight acrylate rubber solution is added, so that the medium resistance of the pressure-sensitive adhesive is greatly improved, and the high temperature resistance of the pressure-sensitive adhesive is improved; polytetrafluoroethylene powder and a fluorine-containing cross-linking agent are added during film preparation, so that the medium resistance of the pressure-sensitive adhesive is further improved, and finally the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive is prepared.
Compared with the prior art, the invention has the advantages that:
1. during synthesis, a certain amount of acrylonitrile and fluorine-containing monomers are used, and a cyano group with strong polarity and a fluorine-containing side chain are introduced into an acrylate main body structure, so that the acrylate pressure-sensitive adhesive has certain medium resistance;
2. the macromolecular acrylate rubber with active functional groups is blended with the pressure-sensitive adhesive solution in a solution form, and the molecular chains of the macromolecular acrylate rubber and the pressure-sensitive adhesive solution form an interpenetrating network structure, so that on one hand, the medium resistance and the high temperature resistance of the pressure-sensitive adhesive are improved by utilizing the excellent anti-resistance and high temperature resistance characteristics of the acrylate rubber, and on the other hand, the high temperature resistance of the pressure-sensitive adhesive is further improved while the compatibility of the acrylate rubber and the pressure-sensitive adhesive is improved by utilizing the reaction of the active functional groups in the acrylate rubber structure and the active functional groups in the main body resin of the pressure-sensitive adhesive;
3. adding polytetrafluoroethylene powder during membrane preparation, and improving the medium resistance of the acrylate pressure-sensitive adhesive by utilizing the hydrophobic and oleophobic properties of the polytetrafluoroethylene; fluorine-containing isocyanate cross-linking agent is used, fluorine element is further introduced, and the medium resistance of the pressure-sensitive adhesive is improved.
Detailed Description
The following detailed description of specific embodiments of the invention is provided, but it should be understood that the scope of the invention is not limited to the specific embodiments.
The following examples were used to demonstrate the beneficial effects of the present invention. It should be understood that the preferred embodiments described herein are only for illustrating and explaining the present invention and are not to be considered as limiting the present invention.
The first specific implementation way is as follows: the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive is prepared from 70-90 parts by weight of soft monomers, 5-15 parts by weight of hard monomers, 7-12 parts by weight of functional monomers, 4-10 parts by weight of modified monomers, 5-15 parts by weight of fluorine-containing monomers, 5-20 parts by weight of acrylate rubber solution, 0.5-1.5 parts by weight of initiator, 80-120 parts by weight of solvent, 5-10 parts by weight of polytetrafluoroethylene powder and 0.2-2.5 parts by weight of fluorine-containing cross-linking agent;
the preparation method of the fluorine-containing cross-linking agent comprises the following steps:
under the protection of nitrogen, adding diisocyanate and fluorine-containing monohydric alcohol into a reactor, adding a catalyst, and reacting at 70-100 ℃ for 3-7 hours to obtain a fluorine-containing cross-linking agent;
the molar ratio of the diisocyanate to the fluorine-containing monohydric alcohol is (5-10) to 1;
the catalyst accounts for 0.1-2.0% of the mass of the diisocyanate.
The second embodiment is as follows: the present embodiment differs from the present embodiment in that: one or more of butyl acrylate, isooctyl acrylate, ethyl acrylate and n-octyl acrylate serving as soft monomers; the functional monomer is one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate and hydroxybutyl methacrylate. Other steps are the same as in the first embodiment.
The third concrete implementation mode: the difference between this embodiment and the first or second embodiment is: the hard monomer is the combination of one or more of methyl methacrylate, styrene, vinyl acetate, ethyl methacrylate, isobutyl methacrylate, isopropyl methacrylate, cyclohexyl methacrylate and isobornyl methacrylate and acrylonitrile; the content of acrylonitrile is at least 5.0wt% of the mass of the hard monomer. The other steps are the same as in the first or second embodiment.
The fourth concrete implementation mode: the difference between this embodiment and one of the first to third embodiments is as follows: the modified monomer is one of glycidyl methacrylate, glycidyl acrylate, allyl glycidyl ether, acrylic acid and methacrylic acid; the fluorine-containing monomer is one or more of perfluoroalkyl ethyl acrylate, perfluoroalkyl ethyl methacrylate, perfluoropropyl acrylate, perfluoropropyl methacrylate, perfluorobutyl ethyl acrylate, perfluorobutyl ethyl methacrylate, perfluorohexyl ethyl acrylate, perfluorohexyl ethyl methacrylate, perfluorooctyl ethyl acrylate, perfluorooctyl ethyl methacrylate, perfluorodecyl ethyl acrylate and perfluorodecyl ethyl methacrylate. The other steps are the same as those in the first to third embodiments.
The fifth concrete implementation mode: the difference between this embodiment and the first to the fourth embodiments is: the mass fraction of the acrylate rubber solution is 1-5%, and the solvent in the acrylate rubber solution is one or two of ethyl acetate and toluene. The other steps are the same as those in the first to fourth embodiments.
The sixth specific implementation mode: the difference between this embodiment and one of the first to fifth embodiments is: when the modified monomer is glycidyl methacrylate, glycidyl acrylate or allyl glycidyl ether, the acrylate rubber in the acrylate rubber solution is carboxyl type acrylate rubber with the carboxyl content of 1-5%; when the modified monomer is acrylic acid or methacrylic acid, the acrylate rubber in the acrylate rubber solution is epoxy acrylate rubber with the epoxy group content of 1-5%. The other steps are the same as those in the first to fifth embodiments.
In the present embodiment, both the carboxyl-type acrylate rubber having a carboxyl group content of 1 to 5% and the epoxy-type acrylate rubber having an epoxy group content of 1 to 5% are available from Sichuan Qinglong acrylate rubber Co.
The seventh embodiment: the difference between this embodiment and one of the first to sixth embodiments is: the initiator is dibenzoyl peroxide or azobisisobutyronitrile; the solvent is one or more of ethyl acetate, butanone, toluene and butyl acetate; the average grain diameter of the polytetrafluoroethylene powder is 0.1-20 mu m. The other steps are the same as those in the first to sixth embodiments.
The specific implementation mode is eight: the difference between this embodiment and one of the first to seventh embodiments is: the diisocyanate is isophorone diisocyanate, dicyclohexylmethane diisocyanate, diphenylmethane diisocyanate, toluene diisocyanate or hexamethylene diisocyanate. The other steps are the same as those in the first to seventh embodiments.
The specific implementation method nine: the difference between this embodiment and the first to eighth embodiments is: the fluorine-containing monohydric alcohol is one or more of hexafluoroisopropanol, hexafluorobutanol, octafluoropentanol, dodecafluoroheptanol, perfluorooctanol and 1H, 1H-perfluoro-1-nonanol; the catalyst is dibutyltin dilaurate, stannous octoate, dibutyltin diacetate, zinc naphthenate, cobalt naphthenate or lead naphthenate. The other steps are the same as those in the first to eighth embodiments.
The detailed implementation mode is ten: the embodiment is a preparation method of medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive, which is completed according to the following steps:
1. preparing a fluorine-containing cross-linking agent:
under the protection of nitrogen, adding diisocyanate and fluorine-containing monohydric alcohol into a reactor, adding a catalyst, and reacting at 70-100 ℃ for 3-7 hours to obtain a fluorine-containing cross-linking agent; the molar ratio of the diisocyanate to the fluorine-containing monohydric alcohol is (5-10) to 1; the catalyst accounts for 0.1-2.0% of the mass of the diisocyanate;
2. weighing 70-90 parts of soft monomer, 5-15 parts of hard monomer, 7-12 parts of functional monomer, 4-10 parts of modified monomer, 5-15 parts of fluorine-containing monomer, 5-20 parts of acrylate rubber solution, 0.5-1.5 parts of initiator, 80-120 parts of solvent, 5-10 parts of polytetrafluoroethylene powder and 0.2-2.5 parts of fluorine-containing cross-linking agent according to parts by weight; dividing an initiator and a solvent into three parts respectively;
3. adding a soft monomer, a hard monomer, a modified monomer, a part of initiator and a part of solvent into a reaction vessel, heating to 75-83 ℃ under the condition of stirring, and reacting for 0.5-1.0 h under the condition of stirring and the temperature of 75-83 ℃;
4. mixing a part of initiator, a part of solvent and fluorine-containing monomer, and dropwise adding the mixed material into the reaction container in the third step at a constant speed within the time range of 1.0-1.5 h;
5. mixing the residual initiator, the residual solvent and the functional monomer, dripping the mixed material into the reaction container in the fourth step at a constant speed within the time range of 0.5-1.5 h, continuing to react after finishing dripping, and stopping when the viscosity is increased to the range of 2500-3000 cp;
6. adding an acrylate rubber solution, polytetrafluoroethylene powder and a fluorine-containing cross-linking agent into the reaction vessel in the fifth step, and uniformly dispersing at a high speed to obtain a glue solution; coating the glue solution on a PET release film by using a 100-600 mu m coater, airing for 0.5-2 h, putting the PET release film into an oven, drying for 1-2 h at the temperature of 100-120 ℃, and transferring the PET release film to an aluminum foil which is anodized by phosphoric acid and has the thickness of 0.03-0.08 mm to obtain the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive.
The following examples were used to demonstrate the beneficial effects of the present invention:
example 1: the preparation method of the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive is completed according to the following steps:
1. preparing a fluorine-containing cross-linking agent: under the protection of nitrogen, adding isophorone diisocyanate and hexafluorobutanol into a reactor, adding dibutyltin dilaurate, and reacting at 80 ℃ for 3 hours to obtain a fluorine-containing crosslinking agent; the molar ratio of the isophorone diisocyanate to the hexafluorobutanol is 8; the dibutyltin dilaurate accounts for 2.0 percent of the mass of the isophorone diisocyanate;
2. weighing 0.5g of the fluorine-containing cross-linking agent prepared in the step one, 40g of n-octyl acrylate, 40g of ethyl acrylate, 2g of acrylonitrile, 10g of isobornyl methacrylate, 8g of hydroxypropyl acrylate, 8g of allyl glycidyl ether, 12g of perfluorohexyl ethyl acrylate, 10g of an acrylate rubber solution with the mass fraction of 5%, 1.0g of dibenzoyl peroxide, 50g of ethyl acetate, 50g of toluene and 8g of polytetrafluoroethylene powder with the average particle size of 1 micron; the acrylic ester rubber solution is ethyl acetate solution of carboxyl type acrylic ester rubber with 5 percent of carboxyl content; dividing dibenzoyl peroxide, ethyl acetate and toluene into three parts respectively;
3. adding n-octyl acrylate, ethyl acrylate, acrylonitrile, isobornyl methacrylate, allyl glycidyl ether, a part of dibenzoyl peroxide, a part of ethyl acetate and toluene into a reaction vessel, heating to 80 ℃ under the condition of stirring, and reacting for 1.0 hour under the condition of stirring and the temperature of 80 ℃;
4. mixing a part of dibenzoyl peroxide, a part of ethyl acetate, toluene and perfluorohexylethyl acrylate, and dropwise adding the mixed material into the reaction container in the third step at a constant speed within the time range of 1.5 h;
5. mixing the rest dibenzoyl peroxide, the rest ethyl acetate, toluene and hydroxypropyl acrylate, dripping the mixed material into the reaction container in the fourth step at a constant speed within the time range of 1.0h, continuing to react after dripping is finished, and stopping when the viscosity is increased to 3000 cp;
6. adding 0.5g of the fluorine-containing cross-linking agent prepared in the first step, polytetrafluoroethylene powder and an acrylate rubber solution into the glue solution prepared in the fourth step, and dispersing uniformly at a high speed to obtain a glue solution; and (3) coating the glue solution on a PET release film by using a 300-micron coater, airing for 0.5h, putting into an oven, drying at the temperature of 120 ℃ for 2h, and transferring to an aluminum foil which is anodized by phosphoric acid and has the thickness of 0.05mm to obtain the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive.
Example 2: the preparation method of the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive is completed according to the following steps:
1. preparing a fluorine-containing cross-linking agent: under the protection of nitrogen, adding isophorone diisocyanate and hexafluorobutanol into a reactor, adding dibutyltin dilaurate, and reacting at 80 ℃ for 3 hours to obtain a fluorine-containing crosslinking agent; the molar ratio of the isophorone diisocyanate to the hexafluorobutanol is 10; the dibutyltin dilaurate accounts for 0.5 percent of the mass of the isophorone diisocyanate;
2. weighing 0.4g of the fluorine-containing cross-linking agent prepared in the step one, 35g of isooctyl acrylate, 40g of butyl acrylate, 1g of acrylonitrile, 15g of methyl methacrylate, 12g of hydroxypropyl acrylate, 8g of glycidyl methacrylate, 12g of perfluoropropyl acrylate, 10g of an acrylate rubber solution with the mass fraction of 5%, 1.0g of dibenzoyl peroxide, 80g of ethyl acetate, 20g of toluene and 5g of polytetrafluoroethylene powder with the average particle size of 1 micron; the acrylic ester rubber solution is ethyl acetate solution of carboxyl type acrylic ester rubber with the carboxyl content of 2 percent; dividing dibenzoyl peroxide, ethyl acetate and toluene into three parts respectively;
3. adding isooctyl acrylate, butyl acrylate, acrylonitrile, methyl methacrylate, glycidyl methacrylate, a part of dibenzoyl peroxide, a part of ethyl ester and toluene into a reaction vessel, heating to 80 ℃ under the condition of stirring, and reacting for 1.0h under the condition of stirring and the temperature of 80 ℃;
4. mixing a part of dibenzoyl peroxide, a part of ethyl acetate, toluene and perfluoropropyl acrylate, and dropwise adding the mixed material into the reaction vessel in the third step at a constant speed within the time range of 1.5 h;
5. mixing the rest dibenzoyl peroxide, the rest ethyl acetate, toluene and hydroxypropyl acrylate, dropwise adding the mixed materials into a reaction container at a constant speed within the time range of 0.5h, continuing to react after dropwise adding, and stopping when the viscosity is increased to 2800 cp;
6. adding 0.4g of the fluorine-containing cross-linking agent prepared in the first step, polytetrafluoroethylene powder and an acrylate rubber solution into the glue solution prepared in the fourth step, and dispersing uniformly at a high speed to obtain a glue solution; and (3) coating the glue solution on a PET release film by using a 300-micron coater, airing for 0.5h, putting into an oven, drying at the temperature of 120 ℃ for 2h, and transferring to an aluminum foil which is anodized by phosphoric acid and has the thickness of 0.05mm to obtain the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive.
Example 3: the preparation method of the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive is completed according to the following steps:
1. preparing a fluorine-containing cross-linking agent: under the protection of nitrogen, adding isophorone diisocyanate and hexafluorobutanol into a reactor, adding dibutyltin dilaurate, and reacting at 80 ℃ for 3 hours to obtain a fluorine-containing crosslinking agent; the molar ratio of isophorone diisocyanate to hexafluorobutanol is 5; the dibutyltin dilaurate accounts for 2% of the mass of the isophorone diisocyanate;
2. weighing 1.0g of the fluorine-containing cross-linking agent prepared in the step one, 85g of isooctyl acrylate, 3g of acrylonitrile, 10g of methyl methacrylate, 10g of hydroxyethyl methacrylate, 8g of acrylic acid, 10g of perfluoro octyl ethyl acrylate, 10g of an acrylate rubber solution with the mass fraction of 5%, 1.0g of dibenzoyl peroxide, 80g of ethyl acetate, 20g of toluene and 5g of polytetrafluoroethylene powder with the average particle size of 1 micron; the acrylic ester rubber solution is an ethyl acetate solution of epoxy acrylic ester rubber with the epoxy group content of 2%; dividing dibenzoyl peroxide, ethyl acetate and toluene into three parts respectively;
3. adding isooctyl acrylate, acrylonitrile, methyl methacrylate, acrylic acid, a part of dibenzoyl peroxide, a part of ethyl acetate and toluene into a reaction container, heating to 80 ℃ under the condition of stirring, and reacting for 1.0h under the condition of stirring and the temperature of 80 ℃;
4. mixing a part of dibenzoyl peroxide, a part of ethyl acetate, toluene and perfluorooctyl ethyl acrylate, and dropwise adding the mixed material into the reaction container in the third step at a constant speed within the time range of 1.5 h;
5. mixing the rest dibenzoyl peroxide, the rest ethyl acetate, toluene and hydroxyethyl methacrylate, dropwise adding the mixed material into a reaction container at a constant speed within the time range of 0.5h, continuing to react after dropwise adding, and stopping when the viscosity is increased to 3000 cp;
6. adding 1.0g of the fluorine-containing cross-linking agent prepared in the first step, polytetrafluoroethylene powder and an acrylate rubber solution into the glue solution prepared in the fourth step, and dispersing uniformly at a high speed to obtain a glue solution; and (3) coating the glue solution on a PET release film by using a 300-micron coater, airing for 0.5h, putting into an oven, drying at the temperature of 120 ℃ for 2h, and then transferring to an aluminum foil which is anodized by phosphoric acid and has the thickness of 0.05mm to obtain the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive.
Comparative example 1: the present example is different from example 1 in that: weighing 0.5g of the fluorine-containing cross-linking agent prepared in the step one, 40g of n-octyl acrylate, 40g of ethyl acrylate, 2g of acrylonitrile, 10g of isobornyl methacrylate, 8g of hydroxypropyl acrylate, 8g of allyl glycidyl ether, 1.0g of dibenzoyl peroxide, 50g of ethyl acetate, 50g of toluene and 8g of polytetrafluoroethylene powder with the average particle size of 1 micrometer; dibenzoyl peroxide, ethyl acetate and toluene were divided into three portions. The other steps and parameters were the same as in example 1.
Comparative example 2: weighing 0.5g of the fluorine-containing cross-linking agent prepared in the step one, 40g of n-octyl acrylate, 40g of ethyl acrylate, 2g of acrylonitrile, 10g of isobornyl methacrylate, 8g of hydroxypropyl acrylate, 8g of allyl glycidyl ether, 12g of perfluorohexyl ethyl acrylate, 1.0g of dibenzoyl peroxide, 50g of ethyl acetate, 50g of toluene and 8g of polytetrafluoroethylene powder with the average particle size of 1 micron; dibenzoyl peroxide, ethyl acetate and toluene were divided into three portions. The other steps and parameters were the same as in example 1.
Comparative example 3: weighing 0.5g of the fluorine-containing cross-linking agent prepared in the step one, 40g of n-octyl acrylate, 40g of ethyl acrylate, 2g of acrylonitrile, 10g of isobornyl methacrylate, 8g of hydroxypropyl acrylate, 8g of allyl glycidyl ether, 10g of an acrylate rubber solution with the mass fraction of 5%, 1.0g of dibenzoyl peroxide, 50g of ethyl acetate, 50g of toluene and 8g of polytetrafluoroethylene powder with the average particle size of 1 micron; the acrylic ester rubber solution is ethyl acetate solution of carboxyl type acrylic ester rubber with 5 percent of carboxyl content; dibenzoyl peroxide, ethyl acetate and toluene were divided into three portions. The other steps and parameters were the same as in example 1.
Comparative example 4: weighing 0.5g of the fluorine-containing cross-linking agent prepared in the step one, 40g of n-octyl acrylate, 40g of ethyl acrylate, 2g of acrylonitrile, 10g of isobornyl methacrylate, 8g of hydroxypropyl acrylate, 8g of allyl glycidyl ether, 12g of perfluorohexyl ethyl acrylate, 10g of an acrylate rubber solution with the mass fraction of 5%, 1.0g of dibenzoyl peroxide, 50g of ethyl acetate, 50g of toluene and 8g of polytetrafluoroethylene powder with the average particle size of 1 micrometer; the acrylic ester rubber solution is an ethyl acetate solution of epoxy acrylic ester rubber with the epoxy group content of 5%; dibenzoyl peroxide, ethyl acetate and toluene were divided into three portions. The other steps and parameters were the same as in example 1.
Comparative example 5: weighing 0.5g of the fluorine-containing cross-linking agent prepared in the step one, 40g of n-octyl acrylate, 40g of ethyl acrylate, 2g of acrylonitrile, 10g of isobornyl methacrylate, 8g of hydroxypropyl acrylate, 8g of allyl glycidyl ether, 12g of perfluorohexyl ethyl acrylate, 10g of an acrylate rubber solution with the mass fraction of 5%, 1.0g of dibenzoyl peroxide, 50g of ethyl acetate and 50g of toluene; the acrylic ester rubber solution is ethyl acetate solution of carboxyl type acrylic ester rubber with 5 percent of carboxyl content; dividing dibenzoyl peroxide, ethyl acetate and toluene into three parts respectively; the other steps and parameters were the same as in example 1.
Comparative example 6: weighing 0.5g of diphenylmethane diisocyanate which does not react with the fluorine-containing monohydric alcohol, 40g of n-octyl acrylate, 40g of ethyl acrylate, 2g of acrylonitrile, 10g of isobornyl methacrylate, 8g of hydroxypropyl acrylate, 8g of allyl glycidyl ether, 12g of perfluorohexyl ethyl acrylate, 10g of an acrylate rubber solution with the mass fraction of 5%, 1.0g of dibenzoyl peroxide, 50g of ethyl acetate, 50g of toluene and 8g of polytetrafluoroethylene powder with the average particle size of 1 micron; the acrylic ester rubber solution is ethyl acetate solution of carboxyl type acrylic ester rubber with the carboxyl content of 5 percent; dividing dibenzoyl peroxide, ethyl acetate and toluene into three parts respectively; the other steps and parameters were the same as in example 1.
Comparative example 7: weighing 0.5g of fluorine-containing cross-linking agent, 40g of n-octyl acrylate, 40g of ethyl acrylate, 10g of isobornyl methacrylate, 8g of hydroxypropyl acrylate, 8g of allyl glycidyl ether, 12g of perfluorohexyl ethyl acrylate, 10g of 5% acrylate rubber solution by mass fraction, 1.0g of dibenzoyl peroxide, 50g of ethyl acetate, 50g of toluene and 8g of polytetrafluoroethylene powder with the average particle size of 1 micrometer; the acrylic ester rubber solution is ethyl acetate solution of carboxyl type acrylic ester rubber with the carboxyl content of 5 percent; dividing dibenzoyl peroxide, ethyl acetate and toluene into three parts respectively; the other steps and parameters were the same as in example 1.
The following performance tests were carried out on the medium-and high-temperature-resistant acrylate pressure-sensitive adhesives prepared in examples 1 to 3 and the acrylate pressure-sensitive adhesives of comparative examples 1 to 7:
testing the 180-degree peel strength of the samples of each pressure-sensitive adhesive tape at 25 ℃,120 ℃ and 25 ℃ after being soaked in different media for 60 ℃/7d according to GB/2792-2014; the results are shown in table 1:
TABLE 1 Performance test Table for pressure-sensitive adhesive tapes
As can be seen from Table 1, the pressure-sensitive adhesives prepared in examples 1 to 3 have good high temperature resistance, the 180-degree peel strength at 120 ℃ is greater than 0.5kN/m, and simultaneously have excellent medium resistance, and the 180-degree peel strength at 25 ℃ is greater than 1.0kN/m after being soaked in RP-3 kerosene, 10# hydraulic oil and 65# cooling liquid at 60 ℃/7 d.
The performance analysis was performed by combining the performance of comparative examples 1 to 6 and example 1, and the specific results are as follows:
(1) By combining the technical schemes of the comparative example 1 and the example 1, the data in the table show that the medium resistance and the high temperature strength of the pressure-sensitive adhesive prepared in the comparative example 1 are obviously lower than those of the pressure-sensitive adhesive prepared in the example 1, which shows that in the technical scheme of the application, the medium resistance and the high temperature resistance of the pressure-sensitive adhesive prepared without adding the fluorine-containing monomer and the acrylic ester rubber solution are poor, and the high temperature resistance and the medium resistance of the pressure-sensitive adhesive can be obviously improved after adding the two components.
(2) By combining the technical schemes of comparative examples 1 and 2 and the technical scheme of example 1, the data in the table show that the medium resistance and the high temperature resistance of the pressure-sensitive adhesive in the comparative example 2 are obviously lower than those of the pressure-sensitive adhesive in the example 1 because no acrylic ester rubber solution is added. Because the fluorine-containing monomer is added in the preparation process, the medium resistance of the pressure-sensitive adhesive in the comparative example 2 is superior to that of the pressure-sensitive adhesive in the comparative example 1, and the temperature resistance of the pressure-sensitive adhesive is slightly superior to that of the pressure-sensitive adhesive in the comparative example 1. This shows that in the technical scheme of the application, the medium resistance and the high temperature resistance of the pressure-sensitive adhesive can be improved to a certain extent only by adding the fluorine-containing monomer without using the acrylate rubber solution, but the improvement degree is not as high as the case of using the fluorine-containing monomer and the acrylate rubber solution at the same time.
(3) By combining the technical schemes of comparative examples 1, 2 and 3 and the technical scheme of example 1, the data in the table show that the medium resistance of the pressure-sensitive adhesive of comparative example 3 is lower than that of the pressure-sensitive adhesive of example 1 due to no addition of the fluorine-containing monomer, and the high temperature resistance is slightly lower. Because the acrylate rubber solution is added in the preparation process, the medium resistance and the high temperature resistance of the pressure-sensitive adhesive in the comparative example 3 are obviously superior to those of the pressure-sensitive adhesive in the comparative example 1 and slightly superior to those of the pressure-sensitive adhesive in the comparative example 2. This shows that in the technical scheme of the application, only the acrylate rubber solution is used, and the fluorine-containing monomer is not added, so that the medium resistance and the high temperature resistance of the pressure-sensitive adhesive can be improved to a certain extent, and the improvement degree is not as good as that of the pressure-sensitive adhesive when the acrylate rubber solution and the fluorine-containing monomer are used simultaneously, but is superior to that when the fluorine-containing monomer is used only.
(4) By combining the technical schemes of comparative examples 1, 2, 3 and 4 and the technical scheme of example 1, the data in the table show that the medium resistance and the high temperature resistance of the pressure-sensitive adhesive of comparative example 4 are slightly lower than those of the pressure-sensitive adhesive of example 1, but are obviously higher than those of comparative examples 1, 2 and 3. According to the technical scheme, if the modified monomer contains an epoxy group, the used acrylate rubber is a carboxyl type, and if the modified monomer contains a carboxyl group, the used acrylate rubber is an epoxy type, and the carboxyl and the epoxy group can react to a certain degree in the cross-linking process, so that the temperature resistance and the medium resistance of the prepared pressure-sensitive adhesive are better.
(5) By combining the technical schemes of the comparative example 5 and the embodiment 1, the data in the table show that the pressure-sensitive adhesive of the comparative example 5 has slightly lower medium resistance than the pressure-sensitive adhesive of the embodiment 1. This shows that in the technical scheme of the application, the addition of a certain amount of polytetrafluoroethylene powder is beneficial to the improvement of the medium resistance.
(6) By combining the technical schemes of the comparative example 6 and the embodiment 1, the data in the table show that the pressure-sensitive adhesive of the comparative example 6 has slightly lower medium resistance than the pressure-sensitive adhesive of the embodiment 1. This shows that in the present embodiment, the pressure-sensitive adhesive prepared by using the fluorine-containing isocyanate crosslinking agent has better medium resistance than the pressure-sensitive adhesive prepared by using the diisocyanate crosslinking agent.
(7) By combining the technical schemes of the comparative example 7 and the embodiment 1, the data in the table show that the pressure-sensitive adhesive of the comparative example 7 has slightly lower high temperature resistance and medium resistance than the pressure-sensitive adhesive of the embodiment 1. This shows that in the technical scheme of the application, the acrylonitrile monomer is beneficial to the improvement of the medium resistance and the high temperature resistance of the pressure sensitive adhesive in the synthesis process.
Claims (10)
1. The medium-resistant high-temperature-resistant acrylate pressure-sensitive adhesive is characterized by being prepared from 70-90 parts by weight of soft monomer, 5-15 parts by weight of hard monomer, 7-12 parts by weight of functional monomer, 4-10 parts by weight of modified monomer, 5-15 parts by weight of fluorine-containing monomer, 5-20 parts by weight of acrylate rubber solution, 0.5-1.5 parts by weight of initiator, 80-120 parts by weight of solvent, 5-10 parts by weight of polytetrafluoroethylene powder and 0.2-2.5 parts by weight of fluorine-containing cross-linking agent;
the preparation method of the fluorine-containing cross-linking agent comprises the following steps:
under the protection of nitrogen, adding diisocyanate and fluorine-containing monohydric alcohol into a reactor, adding a catalyst, and reacting at 70-100 ℃ for 3-7 hours to obtain a fluorine-containing cross-linking agent;
the molar ratio of the diisocyanate to the fluorine-containing monohydric alcohol is (5-10) to 1;
the catalyst accounts for 0.1-2.0% of the mass of the diisocyanate.
2. The medium-resistant high-temperature-resistant acrylate pressure-sensitive adhesive of claim 1, wherein the soft monomers are one or more of butyl acrylate, isooctyl acrylate, ethyl acrylate and n-octyl acrylate; the functional monomer is one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate and hydroxybutyl methacrylate.
3. The medium-resistant high-temperature-resistant acrylate pressure-sensitive adhesive according to claim 2, characterized in that the hard monomer is one or more of methyl methacrylate, styrene, vinyl acetate, ethyl methacrylate, isobutyl methacrylate, isopropyl methacrylate, cyclohexyl methacrylate and isobornyl methacrylate, and is combined with acrylonitrile; the content of acrylonitrile is at least 5.0wt% of the mass of the hard monomer.
4. The medium-temperature-resistant acrylate pressure-sensitive adhesive according to claim 3, wherein the modifying monomer is one of glycidyl methacrylate, glycidyl acrylate, allyl glycidyl ether, acrylic acid and methacrylic acid; the fluorine-containing monomer is one or more of perfluoroalkyl ethyl acrylate, perfluoroalkyl ethyl methacrylate, perfluoropropyl acrylate, perfluoropropyl methacrylate, perfluorobutyl ethyl acrylate, perfluorobutyl ethyl methacrylate, perfluorohexyl ethyl acrylate, perfluorohexyl ethyl methacrylate, perfluorooctyl ethyl acrylate, perfluorooctyl ethyl methacrylate, perfluorodecyl ethyl acrylate and perfluorodecyl ethyl methacrylate.
5. The medium-resistant high-temperature-resistant acrylate pressure-sensitive adhesive according to claim 4, wherein the mass fraction of the acrylate rubber solution is 1-5%, and the solvent in the acrylate rubber solution is one or a mixture of two of ethyl acetate and toluene.
6. The medium-temperature-resistant acrylate pressure-sensitive adhesive according to claim 5, wherein when the modified monomer is glycidyl methacrylate, glycidyl acrylate or allyl glycidyl ether, the acrylate rubber in the acrylate rubber solution is carboxyl-type acrylate rubber with a carboxyl content of 1-5%; when the modified monomer is acrylic acid or methacrylic acid, the acrylate rubber in the acrylate rubber solution is epoxy acrylate rubber with the epoxy group content of 1-5%.
7. The medium-temperature acrylate pressure sensitive adhesive of claim 6, wherein the initiator is dibenzoyl peroxide or azobisisobutyronitrile; the solvent is one or more of ethyl acetate, butanone, toluene and butyl acetate; the average grain diameter of the polytetrafluoroethylene powder is 0.1-20 mu m.
8. The medium-temperature-resistant acrylate pressure-sensitive adhesive according to claim 7, wherein the diisocyanate is isophorone diisocyanate, dicyclohexylmethane diisocyanate, diphenylmethane diisocyanate, toluene diisocyanate or hexamethylene diisocyanate.
9. The medium-temperature-resistant acrylate pressure-sensitive adhesive according to claim 8, wherein the fluorine-containing monohydric alcohol is one or more of hexafluoroisopropanol, hexafluorobutanol, octafluoropentanol, dodecafluoroheptanol, perfluorooctanol and 1H, 1H-perfluoro-1-nonanol; the catalyst is dibutyltin dilaurate, stannous octoate, dibutyltin diacetate, zinc naphthenate, cobalt naphthenate or lead naphthenate.
10. The preparation method of the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive prepared according to the preparation method of claim 1, which is characterized by comprising the following steps of:
1. preparing a fluorine-containing cross-linking agent:
under the protection of nitrogen, adding diisocyanate and fluorine-containing monohydric alcohol into a reactor, adding a catalyst, and reacting at 70-100 ℃ for 3-7 hours to obtain a fluorine-containing cross-linking agent; the molar ratio of the diisocyanate to the fluorine-containing monohydric alcohol is (5-10) to 1; the catalyst accounts for 0.1-2.0% of the mass of the diisocyanate;
2. weighing 70-90 parts of soft monomer, 5-15 parts of hard monomer, 7-12 parts of functional monomer, 4-10 parts of modified monomer, 5-15 parts of fluorine-containing monomer, 5-20 parts of acrylate rubber solution, 0.5-1.5 parts of initiator, 80-120 parts of solvent, 5-10 parts of polytetrafluoroethylene powder and 0.2-2.5 parts of fluorine-containing cross-linking agent according to parts by weight; dividing an initiator and a solvent into three parts respectively;
3. adding a soft monomer, a hard monomer, a modified monomer, a part of initiator and a part of solvent into a reaction vessel, heating to 75-83 ℃ under the condition of stirring, and reacting for 0.5-1.0 h under the condition of stirring and the temperature of 75-83 ℃;
4. mixing a part of initiator, a part of solvent and fluorine-containing monomer, and dropwise adding the mixed material into the reaction container in the third step at a constant speed within the time range of 1.0-1.5 h;
5. mixing the residual initiator, the residual solvent and the functional monomer, dropwise adding the mixed material into the reaction container in the fourth step at a constant speed within the time range of 0.5-1.5 h, continuing the reaction after the dropwise adding is finished, and stopping when the viscosity is increased to the range of 2500-3000 cp;
6. adding an acrylate rubber solution, polytetrafluoroethylene powder and a fluorine-containing cross-linking agent into the reaction vessel in the fifth step, and dispersing uniformly at a high speed to obtain a glue solution; coating the glue solution on a PET release film by using a 100-600 mu m coater, airing for 0.5-2 h, putting the PET release film into an oven, drying for 1-2 h at the temperature of 100-120 ℃, and transferring the PET release film to an aluminum foil which is anodized by phosphoric acid and has the thickness of 0.03-0.08 mm to obtain the medium-resistant and high-temperature-resistant acrylate pressure-sensitive adhesive.
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| CN117165228A (en) * | 2023-09-07 | 2023-12-05 | 嘉兴金门量子材料科技有限公司 | High-viscosity aging-resistant non-yellowing pressure-sensitive adhesive and preparation method and application thereof |
| CN118185518A (en) * | 2024-03-13 | 2024-06-14 | 广州市昌鹏实业有限公司 | High-peel high-temperature-resistant polyacrylate pressure-sensitive adhesive and preparation method and application thereof |
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| CN114479723A (en) * | 2022-02-23 | 2022-05-13 | 哈尔滨工业大学无锡新材料研究院 | High-temperature-resistant fluorine-containing acrylate pressure-sensitive adhesive for bonding fluorine-containing materials |
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| WO2020129781A1 (en) * | 2018-12-21 | 2020-06-25 | 日本ペイント・インダストリアルコーティングス株式会社 | Coating composition for precoated metal plates, precoated metal plate and method for producing same |
| CN112142994A (en) * | 2019-06-27 | 2020-12-29 | 三菱铅笔株式会社 | Nonaqueous dispersions of polytetrafluoroethylene |
| CN114479723A (en) * | 2022-02-23 | 2022-05-13 | 哈尔滨工业大学无锡新材料研究院 | High-temperature-resistant fluorine-containing acrylate pressure-sensitive adhesive for bonding fluorine-containing materials |
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| CN117165228A (en) * | 2023-09-07 | 2023-12-05 | 嘉兴金门量子材料科技有限公司 | High-viscosity aging-resistant non-yellowing pressure-sensitive adhesive and preparation method and application thereof |
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| CN118185518A (en) * | 2024-03-13 | 2024-06-14 | 广州市昌鹏实业有限公司 | High-peel high-temperature-resistant polyacrylate pressure-sensitive adhesive and preparation method and application thereof |
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