CN108728025B - Organic silicon modified high-temperature-resistant pressure-sensitive adhesive, pressure-sensitive adhesive tape and preparation method thereof - Google Patents
Organic silicon modified high-temperature-resistant pressure-sensitive adhesive, pressure-sensitive adhesive tape and preparation method thereof Download PDFInfo
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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
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
- C09J7/25—Plastics; Metallised plastics based on macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
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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
- 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
- C09J7/38—Pressure-sensitive adhesives [PSA]
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- C—CHEMISTRY; METALLURGY
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
- C09J2301/12—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers
- C09J2301/122—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers the adhesive layer being present only on one side of the carrier, e.g. single-sided adhesive tape
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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
- 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
- C09J2301/302—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 pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
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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
- C09J2451/00—Presence of graft polymer
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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
- C09J2477/00—Presence of polyamide
- C09J2477/006—Presence of polyamide in the substrate
Abstract
The invention discloses an organic silicon modified high-temperature-resistant pressure-sensitive adhesive, which is prepared by compounding acrylic acid-2-octyl-1-dodecyl ester and polyester modified acrylic acid functional group-containing dimethyl siloxane, so that the characteristics of a high-temperature-resistant monomer and a high-temperature-resistant organic silicon monomer are efficiently cooperated, excellent compatibility and adaptability are shown, other raw material components are further adjusted to have higher adaptability, the pressure-sensitive adhesive can be subjected to polymerization reaction by adopting a controllable activity polymerization method, and meanwhile, the pressure-sensitive adhesive has the advantages of low modulus, good hydrophobicity, good initial viscosity and good leveling property, and the humidity resistance, heat resistance, impact resistance, aging resistance and the like of the pressure-sensitive adhesive are enhanced. The invention also discloses a preparation method of the pressure-sensitive adhesive, a pressure-sensitive adhesive tape using the pressure-sensitive adhesive and a preparation method of the pressure-sensitive adhesive tape.
Description
Technical Field
The invention relates to the field of high-molecular functional materials, in particular to a pressure-sensitive adhesive.
Background
In recent years, the market in the field of electronics and mechanical manufacture has a great demand for high temperature resistant pressure sensitive adhesive tapes. During the thermal processing, the pressure sensitive adhesive tape may be subjected to a high temperature (120-260 ℃) for a certain period of time (e.g., 30-60 min) to thermally process the surface. The acrylate pressure-sensitive adhesive is the pressure-sensitive adhesive with the widest application range at present, has good transparency, excellent weather resistance and heat resistance, does not have phase separation and migration phenomena, and is suitable for the field of electronic machinery manufacturing.
The acrylate pressure-sensitive adhesives can be classified into pure solvent type acrylic pressure-sensitive adhesives, emulsion type acrylic pressure-sensitive adhesives and solvent-free acrylic pressure-sensitive adhesives. The acrylic pressure-sensitive adhesive has wide molecular weight distribution, poor thermal stability caused by poor molecular chain structure uniformity, can become soft at high temperature and has no practical application, so most common acrylic pressure-sensitive adhesives can only be used at room temperature. Acrylate pressure-sensitive adhesives often require physicochemical modification to partially meet the high temperature resistance requirements. Chinese patents CN104789167A and CN104774579A prepare high temperature resistant adhesive tapes, and when preparing acrylate pressure sensitive adhesives, an alkyl oxygen organosilicon monomer and a crosslinking vinyl organosilicon monomer are added to prepare a high temperature resistant emulsion type organosilicon modified acrylate pressure sensitive adhesive. Although the patent partially improves the high temperature resistance of the acrylate pressure-sensitive adhesive, the comprehensive mechanical property of the finished product prepared by the acrylate pressure-sensitive adhesive is far less than that of a pure solvent type acrylate pressure-sensitive adhesive, such as poor water resistance, easy occurrence of whitening phenomenon in the use process of a moisture environment and the like, and the prepared product cannot meet the environmental protection requirement by catalyzing the crosslinking hydrolysis of an organic silicon monomer by a toxic metal catalyst.
At present, the high-temperature-resistant acrylic pressure-sensitive adhesive mainly surrounds a matching mode, namely, the high-temperature resistance of a matrix is improved by adding a novel cross-linking agent. The pure solvent type acrylic pressure-sensitive adhesive is difficult to achieve good high-temperature resistance and is easy to have high-temperature adhesive residue or ghost phenomenon, and the reason is that the solvent type acrylic pressure-sensitive adhesive is mainly synthesized by free radical polymerization, the copolymer synthesized by the method has wider molecular weight distribution and poor chemical structure uniformity, and the copolymer with small molecular weight has poor heat resistance in a high-temperature environment, so that the phenomenon of adhesive residue or ghost is easy to occur.
Disclosure of Invention
The invention aims to provide an organic silicon modified high-temperature-resistant pressure-sensitive adhesive, and a preparation method and application thereof aiming at the defects of the prior art.
The technical scheme adopted by the invention is as follows: an organic silicon modified high-temperature-resistant pressure-sensitive adhesive comprises the following components in parts by mass:
as a further improvement of the scheme, the synthesis method of the acrylic acid-2-octyl dodecyl ester comprises the following steps: dissolving 30-90 parts by mass of 2-octyldodecanol and 5-50 parts by mass of acrylic acid in 50-100 parts by mass of chloroform, adding 1-10 parts by mass of 4-dimethylaminopyridine and 1-10 parts by mass of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, controlling the temperature to be 20-40 ℃, and reacting for 10-100 hours to prepare the acrylic acid-2-octyldodecyl ester.
The acrylic acid-2-octyl dodecaester is used as a high-temperature resistant monomer, so that the pressure-sensitive adhesive has good high-temperature resistance, and the initial adhesive property is improved, so that the pressure-sensitive adhesive is not easy to decompose to cause ghost or yellowing under the conditions of high-temperature environment and small change of adhesive strength. And the pressure-sensitive adhesive has excellent compatibility and adaptability with N-vinylformamide serving as an adhesion promoting functional monomer and polyester modified acrylic acid functional group-containing dimethyl siloxane serving as an organic silicon monomer, and further improves the stability and the leveling property of the pressure-sensitive adhesive.
As a further improvement of the above scheme, the polyester modified acrylic functional group-containing dimethylsiloxane is BYK 371. Specifically, BYK371 is a polyester modified organosiloxane containing double bonds, and the organosiloxane has good compatibility with the acrylic pressure-sensitive adhesive, wherein the organosiloxane can increase the hydrophobic property and heat resistance of the matrix pressure-sensitive adhesive, reduce the surface tension of the pressure-sensitive adhesive, and show better leveling property and bonding property, so that the problem of bubbles generated in the bonding process is effectively solved.
As a further improvement of the scheme, the free radical initiator is tert-butyl peroxy-2-ethylhexanoate, which further improves the polymerization efficiency of the pressure-sensitive adhesive and is beneficial to polymerizing to form a large molecular weight polymer with uniform structure. The crosslinking agent is an epoxy crosslinking agent GA-240, which further improves the crosslinking strength of the pressure-sensitive adhesive and is beneficial to polymerization to form a high molecular weight polymer with a uniform structure. The polyurethane curing agent is Bayer 3100, which further improves the curing efficiency of the pressure-sensitive adhesive and is beneficial to polymerizing to form a high molecular weight polymer with uniform structure.
As a further improvement of the above scheme, the organic solvent is selected from one of methanol, ethanol, toluene, ethyl acetate and butyl acetate.
The preparation method of the organic silicon modified high-temperature-resistant pressure-sensitive adhesive comprises the following processes: mixing acrylic acid-2-octyldodecyl ester, acrylic acid, N-hydroxyethyl acrylamide, polyester modified dimethyl siloxane containing acrylic acid functional groups, a free radical initiator, 4-cyano-4- (thiobenzoyl) valeric acid and an organic solvent according to the mass parts of the raw materials, carrying out argon deoxidization for 30min, controlling the temperature to be 60-100 ℃, carrying out reversible addition-fragmentation chain transfer polymerization under the protection of argon gas, obtaining a poly (acrylic acid-2-octyldodecyl ester-random-acrylic acid-random-N-hydroxyethyl acrylamide-random-polyester modified dimethyl siloxane containing acrylic acid functional groups) high molecular solution, obtaining a semi-finished product with the viscosity range of the high molecular solution of 1000-6000 cps, adding a cross-linking agent and a polyurethane curing agent, mixing uniformly, and obtaining a finished product of the high-temperature resistant pressure-sensitive adhesive. The viscosity of the poly (acrylic acid-2-octyl dodecyl ester-random-acrylic acid-random-N-hydroxyethyl acrylamide-random-N-vinyl formamide) high polymer solution obtained by polymerization is limited, and good film forming performance is endowed, so that the peel strength of the poly (acrylic acid-2-octyl dodecyl ester-random-acrylic acid-random-N-hydroxyethyl acrylamide-random-N-vinyl formamide) high polymer solution in a high-temperature environment is further improved.
As a further improvement of the scheme, the reaction time of the reversible addition-fragmentation chain transfer polymerization reaction is 5-100 h. Specifically, the limitation of the polymerization reaction time is advantageous for obtaining a high molecular polymer having good chemical structure uniformity.
The utility model provides a pressure-sensitive adhesive tape, its includes pressure-sensitive adhesive layer, polyamide film basic unit and from the type layer from bottom to top, pressure-sensitive adhesive layer from top to bottom organosilicon modified high temperature resistant pressure-sensitive adhesive coating form, the type that produces by the dow corning company is DC 9106's release agent coating and forms from the type layer.
As a further improvement of the scheme, the thickness of the pressure-sensitive adhesive layer is 1-1500 μm; the thickness of the polyamide film base layer is 100-5000 microns; the thickness of the release layer is 1-150 mu m. Specifically, the three-layer-attached thickness of the pressure-sensitive adhesive tape gives excellent adhesion performance. In addition, the pressure-sensitive adhesive has excellent stability, so that the thickness range of the polyamide film base layer in the pressure-sensitive adhesive tape is large, and the pressure-sensitive adhesive tape has wider application prospect.
A preparation method of the pressure-sensitive adhesive tape comprises the following process steps:
1) uniformly coating a release agent on the surface of the polyamide film base layer, and carrying out heat preservation and solidification at 50-160 ℃ for 5-10 min to form a release layer;
2) and then uniformly coating the organic silicon modified high-temperature-resistant pressure-sensitive adhesive on the back surface of the polyamide film base layer in the step 1), placing the polyamide film base layer at 50-160 ℃, preserving heat, drying and curing for 5-60 min to form a pressure-sensitive adhesive layer, and rolling and slitting to obtain the pressure-sensitive adhesive tape.
The invention has the beneficial effects that:
(1) the pressure-sensitive adhesive is compounded by acrylic acid-2-octyl-1-dodecyl ester and polyester modified poly dimethyl siloxane containing acrylic acid functional group, so that the characteristics of the high-temperature resistant monomer and the high-temperature resistant organic silicon monomer are efficiently cooperated, excellent compatibility and adaptability are shown, other raw material components are further adjusted to have higher adaptability, the pressure-sensitive adhesive can be subjected to polymerization reaction by adopting a controllable activity polymerization method (RAFT polymerization), and meanwhile, the pressure-sensitive adhesive has the advantages of low modulus, good hydrophobic property, good initial viscosity property and good leveling property, and the humidity resistance, heat resistance, impact resistance, aging resistance and the like of the pressure-sensitive adhesive are enhanced.
(2) According to the invention, the leveling property of the pressure-sensitive adhesive in the laminating process can be further improved by introducing the organic silicon monomer, so that the pressure-sensitive adhesive is not easy to generate bubbles, and the pressure-sensitive adhesive is endowed with more excellent pressure-sensitive property, wherein the number-average molecular weight Mn is 100000-500000, the molecular polydispersity index is 1.0-1.3, and the glass transition temperature Tg is-50-5 ℃.
(3) The invention adopts the controllable active polymerization method to simultaneously adjust the important parameters of the preparation process, and adopts the double cross-linking curing method, so that the synthesized pressure-sensitive adhesive has excellent uniformity in chemical structure, narrower molecular weight distribution and less small molecular weight polymers, thereby further improving the high temperature resistance of the pressure-sensitive adhesive.
(4) The pressure-sensitive adhesive tape has excellent initial adhesive performance by the special three-layer lamination, and is not easy to decompose to cause ghost or yellowing under the conditions of high-temperature environment and small change of adhesive strength.
Detailed Description
The present invention is specifically described below with reference to examples in order to facilitate understanding of the present invention by those skilled in the art. It should be particularly noted that the examples are given solely for the purpose of illustration and are not to be construed as limitations on the scope of the invention, as non-essential improvements and modifications to the invention may occur to those skilled in the art, which fall within the scope of the invention as defined by the appended claims. Meanwhile, the raw materials mentioned below are not specified in detail and are all commercial products; the process steps or preparation methods not mentioned in detail are all process steps or preparation methods known to the person skilled in the art.
Example 1
A high-temperature-resistant pressure-sensitive adhesive with excellent performance and a pressure-sensitive adhesive tape using the pressure-sensitive adhesive are disclosed, and the preparation process comprises the following steps:
1) synthesis of acrylic acid-2-octyl-1-dodecyl ester monomer
According to the mass parts of the raw materials, 90 parts of 2-octyldodecanol and 25 parts of acrylic acid are dissolved in 100 parts of dichloromethane, 9 parts of 4-dimethylaminopyridine and 9 parts of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride are added, the temperature is controlled at 20 ℃, and the reaction is carried out for 90 hours, so that the 2-octyldodecyl acrylate of the example 1 is prepared.
2) Synthesis of organic silicon modified high-temperature-resistant pressure-sensitive adhesive
Mixing 80 parts of acrylic acid-2-octyl dodecyl ester, 5 parts of acrylic acid, 10 parts of N-hydroxyethyl acrylamide, 8 parts of polyester modified polydimethylsiloxane containing acrylic acid functional groups, 0.008 part of tert-butyl peroxy-2-ethylhexanoate, 0.04 part of 4-cyano-4- (thiobenzoyl) valeric acid and 250 parts of toluene according to the mass parts of raw materials, carrying out argon deoxidization for 30min, controlling the temperature to 90 ℃, carrying out reversible addition-fragmentation chain transfer polymerization reaction for 10h under the protection of argon, obtaining poly (acrylic acid-2-octyl dodecyl ester-random-acrylic acid-random-N-hydroxyethyl acrylamide-random-polyester modified polydimethylsiloxane containing acrylic acid functional groups) high molecular solution, and obtaining the high molecular solution with the viscosity of 5000cps, the number-average molecular weight Mn is 4.3X 105And 3 parts of epoxy cross-linking agent GA-240 and 4 parts of Bayer 3100 are added into the semi-finished product with the molecular polydispersity index (PDI) of 1.28 and mixed evenly to obtain the finished product of the organic silicon modified high-temperature-resistant pressure-sensitive adhesive in the example 1.
3) Preparation of pressure-sensitive adhesive tape
Uniformly coating a release agent (Dow Corning DC9106) on the surface of a polyamide film base layer with the thickness of 1000 mu m, and performing heat preservation and solidification at 140 ℃ for 5min to form a release layer with the thickness of 80 mu m; and then uniformly coating the organic silicon modified high-temperature-resistant pressure-sensitive adhesive on the back surface of the polyamide film base layer in the step 1), placing the polyamide film base layer at 140 ℃, preserving heat, drying and curing for 30min to form a pressure-sensitive adhesive layer with the thickness of 200 mu m, and rolling and slitting to obtain the organic silicon modified high-temperature-resistant pressure-sensitive adhesive tape in the embodiment 1.
Example 2
A high-temperature-resistant pressure-sensitive adhesive with excellent performance and a pressure-sensitive adhesive tape using the pressure-sensitive adhesive are disclosed, and the preparation process comprises the following steps:
1) synthesis of acrylic acid-2-octyl-1-dodecyl ester monomer
75 parts of 2-octyldodecanol and 25 parts of acrylic acid by mass are dissolved in 90 parts of dichloromethane, 8 parts of 4-dimethylaminopyridine and 8 parts of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride are added, the temperature is controlled at 25 ℃, and the reaction is carried out for 80 hours to prepare 2-octyldodecyl acrylate of example 2.
2) Synthesis of organic silicon modified high-temperature-resistant pressure-sensitive adhesive
According to the mass parts of raw materials, 70 parts of acrylic acid-2-octyl dodecyl acrylate, 12 parts of acrylic acid, 5 parts of N-hydroxyethyl acrylamide, 7 parts of polyester modified polydimethylsiloxane containing acrylic functional groups, 0.017 part of tert-butyl peroxy-2-ethylhexanoate, 0.09 part of 4-cyano-4- (thiobenzoyl) valeric acid and 200 parts of methanol are mixed, argon is conducted for deoxidization for 30min, the temperature is controlled at 80 ℃, reversible addition-fragmentation chain transfer polymerization reaction is conducted for 20h under the protection of argon, poly (acrylic acid-2-octyl dodecyl acrylate-random-acrylic acid-random-N-hydroxyethyl acrylamide-random-polyester modified polydimethylsiloxane containing acrylic functional groups) high molecular solution is obtained, the viscosity of the high molecular solution is 4200cps, the number-average molecular weight Mn is 2.8X 105And adding 2 parts of epoxy cross-linking agent GA-240 and 4 parts of Bayer 3100 into the semi-finished product with the molecular polydispersity index (PDI) of 1.23, and uniformly mixing to obtain the finished product of the organic silicon modified high-temperature-resistant pressure-sensitive adhesive in the example 2.
3) Preparation of pressure-sensitive adhesive tape
Uniformly coating a release agent (Dow Corning DC9106) on the surface of a polyamide film base layer with the thickness of 2000 mu m, and performing heat preservation and solidification at 130 ℃ for 15min to form a release layer with the thickness of 130 mu m; and then uniformly coating the organic silicon modified high-temperature-resistant pressure-sensitive adhesive on the back surface of the polyamide film base layer in the step 1), placing the polyamide film base layer at 100 ℃, preserving heat, drying and curing for 20min to form a pressure-sensitive adhesive layer with the thickness of 200 mu m, and rolling and slitting to obtain the organic silicon modified high-temperature-resistant pressure-sensitive adhesive tape in the embodiment 2.
Example 3
A high-temperature-resistant pressure-sensitive adhesive with excellent performance and a pressure-sensitive adhesive tape using the pressure-sensitive adhesive are disclosed, and the preparation process comprises the following steps:
1) synthesis of acrylic acid-2-octyl-1-dodecyl ester monomer
60 parts of 2-octyldodecanol and 20 parts of acrylic acid in parts by mass of the raw materials were dissolved in 60 parts of dichloromethane, 5 parts of 4-dimethylaminopyridine and 5 parts of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride were added, and the temperature was controlled at 30 ℃ to react for 50 hours, thereby preparing 2-octyldodecyl acrylate of example 3.
2) Synthesis of organic silicon modified high-temperature-resistant pressure-sensitive adhesive
Mixing 50 parts of acrylic acid-2-octyl dodecyl ester, 5 parts of acrylic acid, 12 parts of N-hydroxyethyl acrylamide, 3 parts of polyester modified polydimethylsiloxane containing acrylic acid functional groups, 0.035 part of tert-butyl peroxy-2-ethylhexanoate, 0.25 part of 4-cyano-4- (thiobenzoyl) valeric acid and 150 parts of butyl acetate according to the mass parts of the raw materials, carrying out argon deoxidization for 30min, controlling the temperature to be 75 ℃, carrying out reversible addition-fragmentation chain transfer polymerization reaction for 50h under the protection of argon to obtain poly (acrylic acid-2-octyl dodecyl ester-random-acrylic acid-random-N-hydroxyethyl acrylamide-random-polyester modified polydimethylsiloxane containing acrylic acid functional groups), wherein the viscosity of the obtained polymer solution is 2600cps, the number-average molecular weight Mn is 1.7X 105And adding 1 part of epoxy cross-linking agent GA-240 and 4 parts of Bayer 3100 into the semi-finished product with the molecular polydispersity index (PDI) of 1.18 to mix uniformly to obtain the finished product of the organic silicon modified high-temperature-resistant pressure-sensitive adhesive in the example 3.
3) Preparation of pressure-sensitive adhesive tape
Uniformly coating a release agent (Dow Corning DC9106) on the surface of a polyamide film base layer with the thickness of 500 mu m, and performing heat preservation and solidification at 140 ℃ for 8min to form a release layer with the thickness of 10 mu m; and then uniformly coating the organic silicon modified high-temperature-resistant pressure-sensitive adhesive on the back surface of the polyamide film base layer in the step 1), placing the polyamide film base layer at 150 ℃, preserving heat, drying and curing for 5min to form a pressure-sensitive adhesive layer with the thickness of 50 mu m, and rolling and slitting to obtain the organic silicon modified high-temperature-resistant pressure-sensitive adhesive tape in the embodiment 3.
Example 4
A high-temperature-resistant pressure-sensitive adhesive with excellent performance and a pressure-sensitive adhesive tape using the pressure-sensitive adhesive are disclosed, and the preparation process comprises the following steps:
1) synthesis of acrylic acid-2-octyl-1-dodecyl ester monomer
According to the mass parts of the raw materials, 60 parts of 2-octyldodecanol and 20 parts of acrylic acid are dissolved in 60 parts of dichloromethane, 5 parts of 4-dimethylaminopyridine and 5 parts of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride are added, the temperature is controlled at 30 ℃, and the reaction is carried out for 50 hours, so as to prepare the acrylic acid-2-octyldodecyl ester of the example 4.
2) Synthesis of organic silicon modified high-temperature-resistant pressure-sensitive adhesive
Mixing 30 parts of acrylic acid-2-octyl dodecyl acrylate, 1 part of acrylic acid, 4 parts of N-hydroxyethyl acrylamide, 1 part of polyester modified polydimethylsiloxane containing acrylic acid functional groups, 0.045 part of tert-butyl peroxy-2-ethylhexanoate, 0.4 part of 4-cyano-4- (thiobenzoyl) valeric acid and 80 parts of ethyl acetate according to the mass parts of the raw materials, controlling the temperature to 65 ℃ after argon deoxygenation for 30min, carrying out reversible addition-fragmentation chain transfer polymerization reaction for 90h under the protection of argon to obtain poly (acrylic acid-2-octyl dodecyl acrylate-random-acrylic acid-random-N-hydroxyethyl acrylamide-random-polyester modified polydimethylsiloxane containing acrylic acid functional groups) high molecular solution, wherein the viscosity of the high molecular solution is 1200cps, the number-average molecular weight Mn is 0.7X 105And adding 0.5 part of epoxy cross-linking agent GA-240 and 1 part of Bayer 3100 into the semi-finished product with the molecular polydispersity index (PDI) of 1.15, and uniformly mixing to obtain the finished product of the organic silicon modified high-temperature-resistant pressure-sensitive adhesive in the example 4.
3) Preparation of pressure-sensitive adhesive tape
Uniformly coating a release agent (Dow Corning DC9106) on the surface of a polyamide film base layer with the thickness of 4000 micrometers, and performing heat preservation and solidification at 155 ℃ for 70min to form a release layer with the thickness of 20 micrometers; and then uniformly coating the organic silicon modified high-temperature-resistant pressure-sensitive adhesive on the back surface of the polyamide film base layer in the step 1), placing the polyamide film base layer at 150 ℃, preserving heat, drying and curing for 10min to form a pressure-sensitive adhesive layer with the thickness of 40 mu m, and rolling and slitting to obtain the organic silicon modified high-temperature-resistant pressure-sensitive adhesive tape in the embodiment 4.
Example 5: performance testing
The finished product of the organosilicon modified high temperature resistant pressure sensitive adhesive tape obtained in the above 4 embodiments is subjected to the test of the index of the sample for repairing viscosity, 180-degree stripping force and high temperature performance by referring to the current general method for testing the pressure sensitive adhesive tape. The initial tack was tested against the PSTC-6 standard. 180 DEG peel force was tested with reference to the GB/T7122-1996 standard. The specific test method of the high-temperature performance index comprises the steps of adhering the organic silicon modified high-temperature-resistant pressure-sensitive adhesive tape to a stainless steel plate, placing the stainless steel plate in an oven with a set specific temperature for baking for 2 hours, taking out the stainless steel plate, uncovering the adhesive tape when the stainless steel plate is hot and cooling the adhesive tape, observing whether the surface of the stainless steel plate has residual adhesive or not, and observing the denaturation condition of each sample. All test data comparisons are shown in table 1 below. As can be seen from the data in Table 1, the temperature resistance of the organosilicon modified high temperature resistant pressure sensitive adhesive tape prepared from the organosilicon modified high temperature resistant pressure sensitive adhesive synthesized by the invention can reach 220 ℃.
Table 1 testing of the properties of the examples
The above embodiments are preferred embodiments of the present invention, and all similar processes and equivalent variations to those of the present invention should fall within the scope of the present invention.
Claims (9)
1. The organic silicon modified high-temperature-resistant pressure-sensitive adhesive is characterized by comprising the following components in parts by mass:
the free radical initiator is tert-butyl peroxy-2-ethylhexanoate; the cross-linking agent is an epoxy cross-linking agent GA-240; the polyurethane curing agent is Bayer 3100.
2. The silicone-modified high-temperature-resistant pressure-sensitive adhesive according to claim 1, wherein: the synthesis method of the acrylic acid-2-octyl dodecyl ester comprises the following steps: dissolving 30-90 parts by mass of 2-octyldodecanol and 5-50 parts by mass of acrylic acid in 50-100 parts by mass of chloroform, adding 1-10 parts by mass of 4-dimethylaminopyridine and 1-10 parts by mass of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, controlling the temperature to be 20-40 ℃, and reacting for 10-100 hours to prepare the acrylic acid-2-octyldodecyl ester.
3. The silicone-modified high-temperature-resistant pressure-sensitive adhesive according to claim 1, wherein: the polyester modified poly-dimethylsiloxane containing acrylic acid functional group is BYK 371.
4. The silicone-modified high-temperature-resistant pressure-sensitive adhesive according to claim 1, wherein: the organic solvent is selected from one of methanol, ethanol, toluene, ethyl acetate and butyl acetate.
5. A preparation method of the organic silicon modified high temperature resistant pressure sensitive adhesive as claimed in any one of claims 1 to 4, characterized by comprising the following processes: mixing acrylic acid-2-octyldodecyl ester, acrylic acid, N-hydroxyethyl acrylamide, polyester modified dimethyl siloxane containing acrylic acid functional groups, a free radical initiator, 4-cyano-4- (thiobenzoyl) valeric acid and an organic solvent according to the mass parts of the raw materials, carrying out argon deoxidization for 30min, controlling the temperature to be 60-100 ℃, carrying out reversible addition-fragmentation chain transfer polymerization under the protection of argon gas, obtaining a poly (acrylic acid-2-octyldodecyl ester-random-acrylic acid-random-N-hydroxyethyl acrylamide-random-polyester modified dimethyl siloxane containing acrylic acid functional groups) high molecular solution, obtaining a semi-finished product with the viscosity range of the high molecular solution of 1000-6000 cps, adding a cross-linking agent and a polyurethane curing agent, mixing uniformly, and obtaining a finished product of the high-temperature resistant pressure-sensitive adhesive.
6. The preparation method of the organic silicon modified high temperature resistant pressure sensitive adhesive according to claim 5, characterized in that: the reaction time of the reversible addition-fragmentation chain transfer polymerization reaction is 5-100 h.
7. A pressure-sensitive adhesive tape characterized in that: the pressure-sensitive adhesive layer comprises a pressure-sensitive adhesive layer, a polyamide film base layer and a release layer from bottom to top, wherein the pressure-sensitive adhesive layer is formed by coating the organic silicon modified high-temperature-resistant pressure-sensitive adhesive according to any one of claims 1 to 4.
8. The pressure-sensitive adhesive tape according to claim 7, wherein: the thickness of the pressure-sensitive adhesive layer is 1-1500 mu m.
9. A process for the preparation of a pressure-sensitive adhesive tape as claimed in claim 7, characterized in that it comprises the following process steps:
1) uniformly coating a release agent on the surface of the polyamide film base layer, and carrying out heat preservation and solidification at 50-160 ℃ for 5-10 min to form a release layer;
2) and then uniformly coating the organic silicon modified high-temperature-resistant pressure-sensitive adhesive on the back surface of the polyamide film base layer in the step 1), placing the polyamide film base layer at 50-160 ℃, preserving heat, drying and curing for 5-60 min to form a pressure-sensitive adhesive layer, and rolling and slitting to obtain the pressure-sensitive adhesive tape.
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| CN1464017A (en) * | 2002-06-19 | 2003-12-31 | 广州宏昌胶粘带厂 | Process for preparing organosilicon modified acrylic ester high-temperature insulation pressure-sensitive adhesive and adhesive tape |
| CN102105551A (en) * | 2008-06-02 | 2011-06-22 | 3M创新有限公司 | Pressure-sensitive adhesive composition and pressure-sensitive adhesive tape |
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| CN102105551A (en) * | 2008-06-02 | 2011-06-22 | 3M创新有限公司 | Pressure-sensitive adhesive composition and pressure-sensitive adhesive tape |
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