CN115362218A - Resin composition and adhesive tape - Google Patents
Resin composition and adhesive tape Download PDFInfo
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- CN115362218A CN115362218A CN202080099412.9A CN202080099412A CN115362218A CN 115362218 A CN115362218 A CN 115362218A CN 202080099412 A CN202080099412 A CN 202080099412A CN 115362218 A CN115362218 A CN 115362218A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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
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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
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Disclosed is a resin composition comprising a silicone raw gum containing an alkenyl group, an MQ resin, a crosslinking agent, a platinum catalyst and an organic peroxide, the gel percentage after crosslinking being 45% or more and 60% or less, the storage modulus at 200 ℃ after crosslinking being 100000Pa or more and 1000000Pa or less; also disclosed is an adhesive tape having an adhesive layer formed from the resin composition after crosslinking, the adhesive layer having a gel percentage of 45% or more and 60% or less, the adhesive layer having a storage modulus at 200 ℃ of 100000Pa or more and 1000000Pa or less, and the adhesive layer having a thickness of 2 [ mu ] m or more and 10 [ mu ] m or less.
Description
Technical Field
The present invention relates to a resin composition and an adhesive tape which have excellent dimensional stability and are suppressed in adhesive residue when used in a process for producing an electronic component or a semiconductor component.
Background
The silicone adhesive composition is excellent in heat resistance, cold resistance, weather resistance, electrical insulation and chemical resistance. Further, the pressure-sensitive adhesive tape having a silicone pressure-sensitive adhesive layer is less likely to cause adhesive residue when peeled off even when used in a particularly high-temperature environment. Therefore, such an adhesive tape is widely used for protection, shielding, temporary fixing, fixing during transportation, splicing, and the like of members and components in the manufacturing process of electric, electronic, and semiconductor components, for example.
In the production process of these electric, electronic and semiconductor components, there are cases where a high load and a high temperature environment are applied for molding the components. For example, in the production process of a printed laminated board, a fiber-reinforced prepreg impregnated with an uncured resin is laminated as an adhesive layer between circuit laminated boards having circuit patterns formed on the surfaces thereof, and the adhesive layer is formed at a high temperature (for example, 180 ℃ or higher) and a high pressure (for example, 20 kg/cm) 2 The above), a long time (for example, 2 hours or more), and a step of heating and pressing with a laminating press. In such a heat pressing step, it is necessary to protect the surface of the laminated substrate with an adhesive tape or the like in order to prevent the circuit on the surface of the laminated substrate from being damaged and prevent the uncured resin from adhering to the surface.
When a conventional pressure-sensitive adhesive tape having a silicone pressure-sensitive adhesive layer is used in a high-temperature, high-pressure, and long-time heating and pressing step, the pressure-sensitive adhesive layer is pressed out, and a dimensional change of the pressure-sensitive adhesive layer occurs. That is, an overflow occurs from the end of the tape, and the overflow becomes a residual after the tape is peeled off. In such a step, the pressure-sensitive adhesive is pressed against the adherend while being heated at a high temperature. Therefore, the pressure-sensitive adhesive softened at a high temperature is more firmly bonded to the adherend, and the pressure-sensitive adhesive is thermally deteriorated by heating at a high temperature, and the cohesive force is reduced. As a result, when the adhesive tape is peeled off after the heat pressing step, the bonding force between the adherend and the adhesive is stronger than the cohesive force of the adhesive layer, and the adhesive layer is cohesively broken to generate adhesive residue.
There is a tendency that the adhesive residue due to the dimensional change of the adhesive in the heating and pressing process can be reduced by reducing the thickness of the adhesive layer of the adhesive tape. However, when the thickness of the pressure-sensitive adhesive layer is reduced, cohesive force in the thickness direction is reduced, and adhesive residue may occur when the tape is peeled off after the step. On the other hand, if the thickness of the adhesive layer is increased, dimensional stability is lowered, and bleed-out during heating and pressing may increase. As described above, dimensional stability (glue overflow prevention) in the high-temperature process and glue residue prevention after the high-temperature process are in a contradictory relationship, and it is difficult to achieve both of these characteristics.
Patent document 1 discloses a porous fluororesin sheet used as a release protective sheet between a circuit fixing jig and a laminated circuit board in a lamination pressing step for a printed laminated board. However, this release protective sheet is not an adhesive tape because it does not have an adhesive layer. That is, since the fixing force to the specific portion is not provided, the portion to be protected cannot be selectively shielded. Therefore, when the release protective sheet is used, it is necessary to use the release protective sheet over the entire surface to be protected, which is disadvantageous from the viewpoint of cost.
Patent document 2 discloses an adhesive tape including at least a fluororesin film for forming a release surface and an adhesive layer. However, this pressure-sensitive adhesive tape is a pressure-sensitive adhesive tape for mold release, and dimensional stability and residual glue at the time of high-temperature processing have not been investigated. The pressure-sensitive adhesive tape was subjected to a heat and pressure test at 150 ℃ and a pressure of 5kg/cm 2 And 20 minutes pressing, and both of them are looser than a general heating and pressing process such as a heating and pressing process of a laminated substrate.
Patent document 3 discloses a silicone pressure-sensitive adhesive composition containing both a siloxane-based crosslinking agent having an SiH group and a peroxide-based crosslinking agent as crosslinking agents. However, in this silicone pressure-sensitive adhesive composition, the peroxide-based crosslinking agent remains in an unreacted state in the silicone pressure-sensitive adhesive composition before the silicone pressure-sensitive adhesive composition is used in the process. Therefore, it is expected that the peroxide-based crosslinking agent gradually reacts during the course of use before production, storage, shipment, transportation, storage at a customer site, and the like. That is, the properties thereof change before they are actually used in the process, and this is disadvantageous in view of stability with time.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. Hei 04-179520
Patent document 2: international publication No. 2016/174713
Patent document 3: japanese patent laid-open publication No. 2002-275450
Disclosure of Invention
Problems to be solved by the invention
The present inventors have intensively studied to solve problems concerning dimensional stability and adhesive residue of an adhesive tape in applications in which the adhesive tape is used particularly under a high-load and high-temperature environment, among properties required for the adhesive tape. That is, an object of the present invention is to provide a resin composition and an adhesive tape which have excellent dimensional stability when used under a high-load and high-temperature environment and in which adhesive residue is suppressed when peeled off after use under a high-load and high-temperature environment.
Means for solving the problems
The present inventors have conducted extensive studies to achieve the above object, and as a result, have found that a resin composition having specific components and specific physical properties is very effective, and have completed the present invention.
Namely, the present invention is a resin composition comprising an alkenyl group-containing silicone raw gum, an MQ resin, a crosslinking agent, a platinum catalyst and an organic peroxide,
the gel percentage after crosslinking is more than 45% and less than 60%,
the storage modulus at 200 ℃ after crosslinking is 100000Pa or more and 1000000Pa or less.
The present invention also provides an adhesive tape comprising an adhesive layer formed of the resin composition after crosslinking,
the gel percentage of the adhesive layer is 45% or more and 60% or less,
the storage modulus of the pressure-sensitive adhesive layer at 200 ℃ is 100000Pa or more and 1000000Pa or less,
and the thickness of the adhesive layer is 2 μm or more and 10 μm or less.
Effects of the invention
The present invention can provide a resin composition and an adhesive tape that have excellent dimensional stability when used under high-load and high-temperature environments and that suppress adhesive residue when peeled off after used under high-load and high-temperature environments.
The resin composition of the present invention has the above-described effects, and therefore is very useful as a material used for the pressure-sensitive adhesive layer of a pressure-sensitive adhesive tape in particular. The pressure-sensitive adhesive tape of the present invention has the above-described effects, and therefore is very useful for applications such as protection, masking, temporary fixation of an adherend, and the like in, for example, a production process (particularly, a hot pressing process) of an electric, electronic component, and semiconductor.
Detailed Description
< resin composition >
The resin composition of the present invention is a composition comprising a silicone raw gum containing an alkenyl group, an MQ resin, a crosslinking agent, a platinum catalyst and an organic peroxide. The resin composition is particularly useful for use as an adhesive composition (i.e., an addition-curable silicone adhesive composition). However, the resin composition of the present invention is not limited thereto, and can be used for other various applications.
The resin composition of the present invention has a gel percentage after crosslinking of 45% to 60%. If the gel percentage is less than 45%, the storage modulus of the resin composition in a molten state after heating at a high temperature is lowered, and the resin composition tends to bleed. Further, the adhesiveness between the resin composition and the adherend is improved, the cohesive force of the resin composition is reduced, and adhesive residue tends to occur. On the other hand, if the gel percentage is more than 60%, the raw silicone rubber in the resin composition heated at a high temperature is oxidized and cracked, and the cohesive force of the resin composition is reduced, and residual gum tends to be generated. The gel percentage may be 45% to 60%, and particularly 50% to 60%. The specific method of measuring the gel percentage is described in the column of example.
The resin composition of the present invention has a storage modulus at 200 ℃ after crosslinking of 100000Pa or more and 1000000Pa or less. If the storage modulus is less than 100000Pa, the elasticity of the resin composition in a molten state after heating at a high temperature is lowered, and the shape of the resin composition temporarily deformed in a high-temperature step is not so restored to cause flash, for example, in a high load such as a hot pressing step. The storage modulus may be 100000Pa or more and 1000000Pa or less, but particularly 100000Pa or more and 400000Pa or less is more preferable. Specific methods for measuring the storage modulus are described in the column of examples described later.
The raw silicone rubber containing alkenyl groups used in the present invention typically has a structure containing a D unit [ (CH) 3 ) 2 SiO]The long-chain polymer of polydimethylsiloxane of the structure (2) and is a polymer containing at least 2 alkenyl groups per 1 molecule. However, the present invention is not limited to this, and other types of raw silicone rubber may be used.
The MQ resin used in the present invention typically has an M-containing unit [ (CH) 3 ) 3 SiO 1/2 ]And Q unit [ SiO 2 ]The polymer of a silicone resin of (4). However, the present invention is not limited thereto, and MQ resins of other types may be used.
The crosslinking agent used in the present invention is typically a polyorganosiloxane containing at least 2 SiH groups per 1 molecule. However, the present invention is not limited thereto, and crosslinking agents of other types may be used.
The resin composition comprising the raw silicone rubber containing alkenyl group, MQ resin and crosslinking agent as described above is generally known as an addition curing type silicone-based adhesive. The addition curing type silicone adhesive contains, for example: a main agent comprising a silicone raw rubber containing alkenyl groups, an MQ resin and a crosslinking agent comprising a polyorganosiloxane containing SiH groups. The addition-curable silicone adhesive is cured by heating under a platinum catalyst to cause a crosslinking reaction. In addition, it is known that basic adhesive properties such as adhesive force, holding power, and tackiness can be adjusted by changing the ratio of the silicone raw rubber to the MQ resin in the addition curable silicone adhesive.
Various methods are known as a method for adjusting the gel percentage of an addition-curable silicone adhesive. For example, if the mixing ratio of the MQ resin to the silicone raw rubber is decreased, the content ratio of the alkenyl group in the silicone raw rubber (and/or MQ resin) is increased, or the addition amount of the crosslinking agent is increased, the gel percentage after crosslinking tends to be increased. On the other hand, when a non-crosslinking component (e.g., silicone oil or the like) is added, the gel fraction tends to decrease.
Various methods are also known as a method for adjusting the storage modulus of an addition-curable silicone adhesive. For example, increasing the molecular weight of the silicone green rubber, increasing the crosslinking density, and decreasing the blending ratio of the MQ resin to the silicone green rubber tend to increase the storage modulus.
In order to obtain the resin composition of the present invention showing a specific gel percentage and storage modulus, the above respective adjustment methods can be utilized. However, the resin composition of the present invention is not limited to the resin composition obtained by such a conditioning method.
The resin composition of the present invention further comprises a platinum catalyst. The platinum catalyst is a component that promotes the crosslinking reaction after being activated by heating. The type and amount of the platinum catalyst are not particularly limited, and various platinum catalysts and amounts thereof known to be usable as addition curing silicone adhesives can be used. That is, in the present invention, for example, a commercially available platinum catalyst (curing catalyst for addition curing silicone adhesives) may be used in an appropriate amount.
The resin composition of the present invention further comprises an organic peroxide. According to the findings of the present inventors, the organic peroxide is effective not only for exhibiting general characteristics but also for exhibiting the effects of the present invention (such as suppression of cull). Although the reason is not necessarily clear, it is considered that one of the reasons is that free oxygen radicals generated by decomposition of the organic peroxide participate in the crosslinking reaction and appropriately act on the crosslinking density and other characteristics. The percent gel and storage modulus can also be adjusted by varying the content of the organic peroxide.
The type of the organic peroxide is not particularly limited, and any organic peroxide may be used as long as it generates free oxygen radicals after decomposition. Dibenzoyl peroxide and its derivatives are particularly preferred. Specific examples thereof include dibenzoyl peroxide, 4,4' -dimethyldibenzoyl peroxide, 3,3' -dimethyldibenzoyl peroxide, 2,2' -dimethyldibenzoyl peroxide, 2,2',4,4' -tetrachlorodibenzoyl peroxide and cumyl peroxide. The organic peroxide may be used alone in 1 kind, or may be used in combination of 2 or more kinds.
Free oxygen radicals are generated by the decomposition of organic peroxides. The stoichiometry (i.e., the theoretical active oxygen amount of the organic peroxide) is calculated by the following formula (1).
A(％)＝(B×16/M)×100 (1)
[ in the formula (1), A represents the theoretical active oxygen amount of the organic peroxide, B represents the number of peroxide bonds, and M represents the molecular weight of the organic peroxide. ]
In the present invention, the amount of the organic peroxide is not particularly limited as long as it is appropriately determined according to various conditions such as the curing temperature, the decomposition temperature of the organic peroxide, the ratio of the silicone raw rubber to the MQ resin, the molecular weight of the silicone component, and the like. However, PA, which is the product of the amount P (parts by mass) of the organic peroxide and the theoretical active oxygen amount a (%) of the organic peroxide represented by the above formula (1), is preferably 0.06 parts by mass or more, and more preferably 0.10 parts by mass or more and 0.30 parts by mass or less, per 100 parts by mass of the total of the alkenyl group-containing silicone raw rubber, MQ resin, and crosslinking agent described above. By changing the product PA, the gel percentage and the storage modulus can be adjusted.
The components described above are available as commercially available products, for example. For example, the resin composition of the present invention can be obtained by adding a predetermined amount of a commercially available platinum catalyst and an organic peroxide to a commercially available addition curing silicone adhesive. However, it is necessary to appropriately adjust the composition and other conditions in such a manner that the gel percentage, the storage modulus are within the range of the present invention. Further, by crosslinking and curing the resin composition, a resin composition containing a silicone structure after crosslinking can be obtained, and the resin composition exerts the effects of the present invention. The crosslinking curing reaction is generally carried out by heating. However, crosslinking and curing can be performed by ultraviolet irradiation depending on the kind of each component.
The resin composition of the present invention can be obtained, for example, by using a mixture of 2 or more commercially available silicone adhesives, a commercially available platinum catalyst, and an organic peroxide. Specifically, for example, the resin composition of the present invention can be obtained by mixing a silicone-based binder having a high gel percentage and a high storage modulus and a silicone-based binder having a low gel percentage and a low storage modulus at an appropriate ratio, and blending a platinum catalyst and an appropriate amount of an organic peroxide. However, the resin composition of the present invention is not limited to the resin composition obtained by such a method.
In the resin composition of the present invention, additives may be added for the purpose of improving various properties. Specific examples of the additive include inorganic fillers such as carbon black and silica; polyorganosiloxanes such as silicone resins, polydimethylsiloxanes, and polydimethylphenylsiloxanes; antioxidants such as phenol antioxidants and amine antioxidants; a silane coupling agent.
< adhesive tape >
The adhesive tape of the present invention is an adhesive tape having an adhesive layer formed of the resin composition of the present invention after crosslinking. The pressure-sensitive adhesive tape may be a pressure-sensitive adhesive tape having the pressure-sensitive adhesive layer on one surface or both surfaces of a substrate film, or may be a substrate-free pressure-sensitive adhesive tape having no substrate. The double-sided pressure-sensitive adhesive tape may have a pressure-sensitive adhesive layer formed of the resin composition of the present invention after crosslinking on one surface of a substrate and another pressure-sensitive adhesive layer (conventional pressure-sensitive adhesive layer) on the other surface.
The thickness of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive tape is 2 μm or more and 10 μm or less, preferably 4 μm or more and 8 μm or less. By setting the thickness of the pressure-sensitive adhesive layer to 2 μm or more and 10 μm or less, dimensional stability is improved when used under a high load and high temperature environment, and adhesive residue tends to be suppressed.
The adhesive layer may be formed by subjecting the resin composition of the present invention to a crosslinking curing reaction. For example, the resin composition may be applied to a substrate, and crosslinked and cured by heating or ultraviolet irradiation to form an adhesive layer on the substrate. Alternatively, the resin composition may be applied to release paper or another film, crosslinked and cured by heating or ultraviolet irradiation to form an adhesive layer, and the adhesive layer may be bonded to one or both surfaces of the substrate. The adhesive tape of the non-substrate type can be manufactured by forming an adhesive layer on a release paper or other film and then attaching another release paper or other film on the adhesive layer.
In order to reduce the viscosity of the resin composition at the time of coating, a solvent may be added. Specific examples of the solvent include aromatic solvents such as toluene and xylene; aliphatic solvents such as hexane, octane and isoparaffin; ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone; ester solvents such as ethyl acetate and isobutyl acetate; ether solvents such as diisopropyl ether and 1,4-dioxane.
The coating method is not particularly limited as long as a known method is used. Specific examples thereof include coating using a comma type knife coater, a die lip coater, a roll coater, a die coater, a knife coater, a blade coater, a bar coater, a kiss coater, or a gravure coater; screen coating; dip coating; and (4) casting and coating.
The substrate is not particularly limited, but a film-like substrate is preferable. Particularly, a resin film having high heat resistance which can be processed at high temperature is preferable. Specific examples thereof include resin films such as Polyimide (PI), polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK), polyphenylene sulfide (PPS), and Polytetrafluoroethylene (PTFE). These films may be used in the form of a single layer, or a laminate of 2 or more layers. Among them, polyimide films are preferable. The thickness of the substrate is not particularly limited, but is preferably 5 to 200. Mu.m, more preferably 5 to 125. Mu.m.
Further, the surface of the substrate on which the pressure-sensitive adhesive layer is provided may be subjected to an easy-adhesion treatment as needed. Examples of the easy adhesion treatment include an undercoating treatment, a corona treatment, an etching treatment, a plasma treatment, and a blast treatment.
The adhesive tape of the present invention may be provided with a release liner. The release liner is a member for protecting the pressure-sensitive adhesive layer of the pressure-sensitive adhesive tape, and is peeled off immediately before the attachment to expose the pressure-sensitive adhesive, and then the pressure-sensitive adhesive tape is attached to an adherend. The type of the release liner is not particularly limited, and a known release liner can be used. Specific examples thereof include release liners obtained by subjecting the surface of a base material such as high-grade paper, cellophane, or synthetic resin film to a release agent treatment. In the treatment of the release agent, for example, a release agent such as a fluorine-substituted alkyl-modified silicone resin may be used. In particular, as the release liner laminated on the silicone pressure-sensitive adhesive layer, a release liner obtained by subjecting the surface of a polyethylene terephthalate film to a release treatment with a fluorine-substituted alkyl-modified silicone resin is preferable. In addition, when the adhesiveness of the pressure-sensitive adhesive layer is low, a resin film which is not subjected to a release treatment can be used as the release liner. Specific examples thereof include a polyethylene terephthalate (PET) film, a Polyethylene (PE) film, and a polypropylene (PP) film.
Examples
The present invention will be described in further detail below with reference to examples. However, the present invention is not limited to these examples. In the following description, "part" means "part by mass".
< example 1>
First, a plurality of samples (a to F) of an addition curing silicone adhesive (stock solution) were prepared. These test pieces were adhesive test pieces adjusted so that the storage modulus G' and the gel percentage after curing measured by the method described later showed various values. These samples were silicone adhesives containing a silicone raw rubber containing an alkenyl group, an MQ resin, and a crosslinking agent.
In example 1, among the plurality of samples, the addition-curable silicone adhesive (a) (solid content concentration 60%) was selected so that the storage modulus G' and the gel percentage after curing when an organic peroxide was added in an appropriate amount were the specific values described later.
Thereafter, 100 parts of the addition curing type silicone adhesive stock solution (A), 197 parts of toluene as a diluent solvent, 3.0 parts of an organic peroxide type curing agent (Nyper (Japanese: ナイパ one) (registered trademark) BMT-K40, concentration of the organic peroxide: 40%, theoretical active oxygen amount in the organic peroxide: 6.05%) as an organic peroxide, and 0.3 parts of a platinum catalyst (NC-25, manufactured by Dow Toray Co., ltd.) were uniformly mixed to obtain an adhesive solution (1). In the adhesive liquid (1), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount a of the organic peroxide is 0.12 part per 100 parts of the silicone adhesive.
The adhesive liquid (1) was subjected to the dynamic viscoelasticity measurement described later, and the storage modulus G' at 200 ℃ was 168628Pa. The adhesive liquid (1) was subjected to gel percentage measurement described later, and the gel percentage was 46%.
Then, the adhesive liquid (1) was applied to one surface of the primed Polyimide (PI) film having a thickness of 25 μm so that the thickness of the dried adhesive layer was 6 μm, dried in a drying oven at 60 ℃ for 1 minute to remove the solvent, and cured by heating at 200 ℃ for 1 minute to form the adhesive layer. Thereafter, a polyethylene terephthalate (PET) film having a thickness of 50 μm, which was subjected to release treatment with a fluorine-substituted alkyl-modified silicone resin, was bonded to the pressure-sensitive adhesive layer as a release liner to obtain a pressure-sensitive adhesive tape.
[ measurement of dynamic viscoelasticity ]
The adhesive liquid (1) was coated on a release liner so that the thickness after drying was 50 μm. The mixture was then dried in a drying oven at 60 ℃ for 1 minute to remove the solvent. Thereafter, the silicone component was cured by heating at 200 ℃ for 1 minute, and an adhesive layer containing the cured silicone adhesive composition was formed. This operation was repeated a plurality of times to form a laminate of adhesive layers having a thickness of 2mm, which was used as a sample for measurement.
The measurement sample was held between parallel disks (. Phi.8 mm), and the storage modulus G' was measured in a range of-60 ℃ to 300 ℃ at a temperature increase rate of 10 ℃/min while applying a shear strain at a frequency of 10Hz using a dynamic viscoelasticity measuring apparatus (manufactured by Rheometric Scientific Co., ltd., apparatus name RDAIII).
[ measurement of percent gel ]
The adhesive liquid (1) was coated on a release liner so that the thickness after drying was 50 μm. The mixture was then dried in a drying oven at 60 ℃ for 1 minute to remove the solvent. Thereafter, the silicone component was cured by heating at 200 ℃ for 1 minute, and a pressure-sensitive adhesive layer containing the cured silicone pressure-sensitive adhesive composition was formed and used as a sample for measurement.
The obtained sample was cut into 50mm × 50mm, and the release liner was peeled off to obtain a sheet-like sample for measurement containing a silicone adhesive composition. Thereafter, the measurement sample was immersed in toluene in an amount of 250 times or more the initial mass (X) at room temperature (23 ℃) for 1 day to swell. After the immersion, the sample for measurement was taken out, dried in a dryer at 130 ℃ for 2 hours, and the absorbed solvent was removed to measure the dry mass (Y) (= mass of the dried silicone adhesive composition). The percent gel of the silicone-based adhesive composition was obtained using the following formula.
Percent gel (%) = (Y/X). Times.100%
< example 2>
A pressure-sensitive adhesive tape (2) was prepared in the same manner as in example 1 except that a mixture of 50 parts of the addition-curable silicone pressure-sensitive adhesive stock solution (a) (solid content concentration 40%) and 50 parts of the addition-curable silicone pressure-sensitive adhesive stock solution (B) (solid content concentration 40 mass%) was used in place of 100 parts of the addition-curable silicone pressure-sensitive adhesive stock solution (a) (solid content concentration 60%), and the amount of the organic peroxide was changed to 2.5 parts, to thereby prepare a pressure-sensitive adhesive tape. In the adhesive liquid (2), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide was 0.12 part. The adhesive liquid (2) was subjected to dynamic viscoelasticity measurement and gel percentage measurement, and the storage modulus G' at 200 ℃ was 124121Pa and the gel percentage was 55%.
< example 3>
A pressure-sensitive adhesive liquid (3) was prepared and a pressure-sensitive adhesive tape was produced in the same manner as in example 2, except that the amount of the organic peroxide was changed to 4.5 parts by mass. In the adhesive liquid (3), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide was 0.22 part. The adhesive liquid (3) was subjected to dynamic viscoelasticity measurement and gel percentage measurement, and as a result, the storage modulus G' at 200 ℃ was 219861Pa and the gel percentage was 60%.
< comparative example 1>
A pressure-sensitive adhesive liquid (C1) was prepared and a pressure-sensitive adhesive tape was produced in the same manner as in example 2, except that the amount of the addition-curable silicone pressure-sensitive adhesive stock solution (a) was changed to 25 parts, the amount of the addition-curable silicone pressure-sensitive adhesive stock solution (B) was changed to 75 parts, and the amount of the organic peroxide was changed to 2.25 parts. In the adhesive liquid (C1), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide was 0.12 part. The adhesive liquid (C1) was subjected to dynamic viscoelasticity measurement and gel percentage measurement, and as a result, the storage modulus G' at 200 ℃ was 125270Pa and the gel percentage was 62%.
< comparative example 2>
A pressure-sensitive adhesive tape was produced by preparing a pressure-sensitive adhesive liquid (C2) in the same manner as in example 1 except that 100 parts of an addition-curable silicone pressure-sensitive adhesive stock solution (B) (solid content concentration 40%) was used instead of 100 parts of the addition-curable silicone pressure-sensitive adhesive stock solution (a) (solid content concentration 60%) and the amount of the organic peroxide was changed to 2 parts. In the adhesive liquid (C2), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide was 0.12 part. The adhesive liquid (C2) was subjected to dynamic viscoelasticity measurement and gel percentage measurement, and as a result, the storage modulus G' at 200 ℃ was 136757Pa and the gel percentage was 69%.
< comparative example 3>
A pressure-sensitive adhesive liquid (C3) was prepared in the same manner as in example 2, except that the organic peroxide was not added, and a pressure-sensitive adhesive tape was produced. In the adhesive liquid (C3), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide is 0 part. The adhesive liquid (C3) was subjected to dynamic viscoelasticity measurement and gel percentage measurement, and as a result, the storage modulus G' at 200 ℃ was 240508Pa and the gel percentage was 53%.
< comparative example 4>
A pressure-sensitive adhesive solution (C4) was prepared and a pressure-sensitive adhesive tape was produced in the same manner as in example 1, except that a mixture of 25 parts by weight of the addition-curable silicone pressure-sensitive adhesive stock solution (C) (solid content concentration 90% by mass) and 75 parts by weight of the addition-curable silicone pressure-sensitive adhesive stock solution (D) (solid content concentration 90% by mass) was used instead of 100 parts by weight of the addition-curable silicone pressure-sensitive adhesive stock solution (a) (solid content concentration 60%), and the amount of the organic peroxide was changed to 4.5 parts. In the binder liquid (C4), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide was 0.12 part. The adhesive liquid (C4) was subjected to dynamic viscoelasticity measurement and gel percentage measurement, and as a result, the storage modulus G' at 200 ℃ was 17620Pa, and the gel percentage was 48%.
< comparative example 5>
A pressure-sensitive adhesive liquid (C5) was prepared and a pressure-sensitive adhesive tape was produced in the same manner as in example 1, except that 100 parts of the addition-curable silicone pressure-sensitive adhesive stock solution (E) (solid content concentration 60 mass%) was used instead of 100 parts of the addition-curable silicone pressure-sensitive adhesive stock solution (a) (solid content concentration 60%). In the adhesive liquid (C5), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide was 0.12 part. The adhesive liquid (C5) was subjected to dynamic viscoelasticity measurement and gel percentage measurement, and as a result, the storage modulus G' at 200 ℃ was 98880Pa and the gel percentage was 44%.
< comparative example 6>
A pressure-sensitive adhesive liquid (C6) was prepared and a pressure-sensitive adhesive tape was produced in the same manner as in comparative example 5, except that the organic peroxide was not added. In the adhesive liquid (C6), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide is 0 part. The adhesive liquid (C6) was subjected to dynamic viscoelasticity measurement and gel percentage measurement, and as a result, the storage modulus G' at 200 ℃ was 69702Pa and the gel percentage was 34%.
< comparative example 7>
A pressure-sensitive adhesive solution (C7) was prepared and a pressure-sensitive adhesive tape was produced in the same manner as in comparative example 6, except that 100 parts of the addition-curable silicone pressure-sensitive adhesive stock solution (F) (solid content concentration 60 mass%) was used instead of 100 parts of the addition-curable silicone pressure-sensitive adhesive stock solution (E) (solid content concentration 60 mass%). In the adhesive liquid (C7), the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide is 0 part. The adhesive liquid (C7) was subjected to dynamic viscoelasticity measurement and gel percentage measurement, and as a result, the storage modulus G' at 200 ℃ was 69045Pa and the gel percentage was 44%.
< reference example 1>
A pressure-sensitive adhesive tape was produced in the same manner as in example 2, except that the thickness of the pressure-sensitive adhesive layer was changed to 13 μm.
The adhesive tapes of the above examples and comparative examples were evaluated as follows. The results are shown in table 1.
[ measurement of Overflow after Hot pressing and residual after peeling ]
The adhesive tape cut to 20mm × 20mm was attached to a Cu plate (Cl 100 p) whose surface was polished with a PIKAL polishing liquid (manufactured by japan abrasives industries, ltd.), and pressure-bonded by reciprocating 1 time with a roller having a weight of 2kg and coated with a rubber layer. Thereafter, the sample was left at 23 ℃ for 20 minutes to 1 hour to obtain a measurement bonded sample. The sample was sandwiched between 2 SUS304 plates mirror-finished on both sides, and the temperature was 200 ℃ and the pressure was 30kg/cm 2 Heating and pressing are carried out for 4 hours. The flash after heating and the residual after peeling the tape were observed at a magnification of 100 times using a microscope (VHX-6000, manufactured by KEYENCE Co., ltd.) and evaluated based on the following criteria.
(flash after hot pressing)
"] in the following ratio: no flash from the 4 sides or corners was observed.
"×": flash from 4 sides or corners was observed.
(residual glue after hot pressing)
O: no adhesive residue was observed on the adhesive surface.
X: residual glue was observed on the adhesive side.
[ Table 1]
< evaluation results >
As shown in Table 1, the adhesive tapes of examples 1 to 3 did not cause residual or flash after hot pressing at 200 ℃.
Comparative examples 1 and 2 are examples in which the gel percentage of the adhesive composition after crosslinking was too high. As a result, adhesive residue was generated in the adhesive tapes of comparative examples 1 and 2.
Comparative example 3 is an example in which no organic peroxide was used in the adhesive composition. As a result, a residual adhesive was generated in the pressure-sensitive adhesive tape of comparative example 3.
Comparative example 4 is an example in which the storage modulus after crosslinking of the adhesive composition is too low. As a result, flash and residue occurred in the pressure-sensitive adhesive tape of comparative example 4.
Comparative example 5 is an example in which the gel percentage and storage modulus of the adhesive composition after crosslinking are too low. As a result, flash and residue occurred in the pressure-sensitive adhesive tape of comparative example 4.
Comparative examples 6 and 7 are examples in which no organic peroxide was used in the adhesive composition, and the gel percentage and storage modulus of the adhesive composition after crosslinking were too low. As a result, flash and residue occurred in the adhesive tapes of comparative examples 6 and 7.
Reference example 1 is an example in which the thickness of the adhesive layer was too large. As a result, flash and residue were generated in the pressure-sensitive adhesive tape of reference example 1. From the results, it is understood that when the resin composition (adhesive composition) of the present invention is used for an adhesive layer of an adhesive tape, the thickness of the adhesive layer is preferably relatively thin.
Industrial applicability
The resin composition of the present invention is particularly useful as a material for forming an adhesive layer of an adhesive tape, for example. The pressure-sensitive adhesive tape of the present invention is subjected to a high temperature (for example, 180 ℃ or higher) and a high pressure (for example, 20 kg/cm) in a step requiring treatment under a high-load and high-temperature environment, for example, in a step of producing a printed laminated substrate 2 Above) intoThe step of heating and pressing for a long time (for example, 2 hours or longer) is very useful for the purposes of protecting, shielding, temporarily fixing, and fixing during transportation of an adherend (for example, the surface of a laminated substrate).
Claims (3)
1. A resin composition comprising an alkenyl group-containing silicone raw gum, an MQ resin, a crosslinking agent, a platinum catalyst and an organic peroxide,
the gel percentage after crosslinking is more than 45% and less than 60%,
the storage modulus at 200 ℃ after crosslinking is 100000Pa or more and 1000000Pa or less.
2. The resin composition according to claim 1, wherein,
the product PA of the amount P of the organic peroxide and the theoretical active oxygen amount A of the organic peroxide shown in the following formula (1) relative to 100 parts by mass of the total amount of the alkenyl-containing silicone raw rubber, the MQ resin and the cross-linking agent is more than 0.06 part by mass, wherein the unit of P is part by mass, and A is a% value;
A＝(B×16/M)×100 (1)
in the formula (1), A represents the theoretical active oxygen amount of the organic peroxide, B represents the number of peroxide bonds, and M represents the molecular weight of the organic peroxide.
3. An adhesive tape having an adhesive layer formed of the resin composition according to claim 1 after crosslinking,
the adhesive layer has a gel percentage of 45% or more and 60% or less,
a storage modulus at 200 ℃ of the pressure-sensitive adhesive layer is 100000Pa or more and 1000000Pa or less, and
the thickness of the adhesive layer is 2 [ mu ] m or more and 10 [ mu ] m or less.
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| Application Number | Priority Date | Filing Date | Title |
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| PCT/JP2020/014952 WO2021199355A1 (en) | 2020-03-31 | 2020-03-31 | Resin composition and adhesive tape |
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| CN115362218A true CN115362218A (en) | 2022-11-18 |
| CN115362218B CN115362218B (en) | 2023-09-19 |
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| JP (1) | JPWO2021199355A1 (en) |
| KR (1) | KR20230004554A (en) |
| CN (1) | CN115362218B (en) |
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| TW202144504A (en) | 2021-12-01 |
| WO2021199355A1 (en) | 2021-10-07 |
| KR20230004554A (en) | 2023-01-06 |
| CN115362218B (en) | 2023-09-19 |
| JPWO2021199355A1 (en) | 2021-10-07 |
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