WO2015152006A1 - Polymère cristallin à chaîne latérale, agent adhésif thermosensible, feuille adhésive thermosensible et ruban adhésif thermosensible - Google Patents

Polymère cristallin à chaîne latérale, agent adhésif thermosensible, feuille adhésive thermosensible et ruban adhésif thermosensible Download PDF

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Publication number
WO2015152006A1
WO2015152006A1 PCT/JP2015/059439 JP2015059439W WO2015152006A1 WO 2015152006 A1 WO2015152006 A1 WO 2015152006A1 JP 2015059439 W JP2015059439 W JP 2015059439W WO 2015152006 A1 WO2015152006 A1 WO 2015152006A1
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Prior art keywords
acrylate
meth
crystalline polymer
temperature
sensitive adhesive
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PCT/JP2015/059439
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English (en)
Japanese (ja)
Inventor
聡士 山口
伸一郎 河原
実 南地
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Nitta Corp
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Nitta Corp
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Priority to CN201580016430.5A priority Critical patent/CN106133011B/zh
Priority to JP2016511596A priority patent/JP6695271B2/ja
Priority to KR1020167025294A priority patent/KR102310619B1/ko
Publication of WO2015152006A1 publication Critical patent/WO2015152006A1/fr
Anticipated expiration legal-status Critical
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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
    • 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
    • C08F220/38—Esters containing sulfur
    • C08F220/382—Esters containing sulfur and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • C08F290/046—Polymers of unsaturated carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
    • 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
    • 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
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • 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
    • C09J155/00—Adhesives based on homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C09J123/00 - C09J153/00
    • C09J155/005—Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • 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
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • 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]
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer
    • 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

Definitions

  • the present invention relates to a side chain crystalline polymer, a thermosensitive adhesive, a thermosensitive adhesive sheet, and a thermosensitive adhesive tape.
  • the temperature-sensitive adhesive contains a pressure-sensitive adhesive and a side chain crystalline polymer, and the adhesive strength decreases at a temperature equal to or higher than the melting point of the side chain crystalline polymer.
  • a temperature-sensitive adhesive tape which is one usage form of a temperature-sensitive adhesive, is used for temporarily fixing parts in the fields of electronic parts, semiconductor wafers, liquid crystals, and the like (see, for example, Patent Document 1).
  • the conventional side chain crystalline polymer as described in Patent Document 1 is composed of a random copolymer.
  • the temperature-sensitive adhesive those having excellent adhesive properties are desirable.
  • An object of the present invention is to provide a side-chain crystalline polymer that can be used as a temperature-sensitive adhesive having excellent adhesive properties, a temperature-sensitive adhesive, a temperature-sensitive adhesive sheet, and a temperature-sensitive adhesive tape containing the side-chain crystalline polymer. That is.
  • the side chain crystalline polymer of the present invention comprises a graft copolymer of a crystalline macromonomer and an amorphous monomer.
  • the temperature-sensitive pressure-sensitive adhesive of the present invention contains an acrylic pressure-sensitive adhesive and the side chain crystalline polymer, and the adhesive force is lowered at a temperature equal to or higher than the melting point of the side chain crystalline polymer.
  • the temperature-sensitive adhesive sheet of the present invention comprises the temperature-sensitive adhesive.
  • the temperature sensitive adhesive tape of this invention is equipped with a base film and the adhesive layer which consists of the said temperature sensitive adhesive laminated
  • the side chain crystalline polymer of this embodiment is, for example, a graft copolymer represented by the following general formula (I).
  • R 1 represents a linear alkyl group having 16 or more carbon atoms.
  • R 2 represents a hydrogen atom or a methyl group.
  • R 3 and R 4 are the same or different groups, and each represents an alkyl group having 1 to 12 carbon atoms.
  • n represents an integer of 2 to 80.
  • the side chain crystalline polymer represented by the general formula (I) described above is a graft copolymer of a crystalline macromonomer represented by the following general formula (II) and an amorphous monomer.
  • R 1, R 2 and n are the same as R 1, R 2 and n in the general formula (I).
  • the crystalline macromonomer represented by the general formula (II) constitutes a branch part of the graft copolymer, and is a site that functions as a crystalline component in the graft copolymer.
  • the non-crystalline monomer is a site that constitutes the trunk (main chain) of the graft copolymer and functions as a component compatible with the acrylic pressure-sensitive adhesive described later.
  • the conventional side chain crystalline polymer described above is composed of a random copolymer, the crystalline component and the compatible component are also randomly present in the copolymer, and each component is difficult to function sufficiently. It is inferred that In the side chain crystalline polymer of this embodiment, since the crystalline component and the compatible component are separately present in the copolymer, the function of each component is fully exhibited, and as a result, the temperature-sensitive adhesive It is presumed that when it is used as an agent, it exhibits an excellent effect on the adhesive physical properties. Specifically, when the side-chain crystalline polymer of this embodiment is included in an acrylic pressure-sensitive adhesive to form a temperature-sensitive adhesive, the initial adhesive force is sufficient at a temperature below the melting point of the side-chain crystalline polymer. The adhesive strength can be sufficiently reduced at a temperature equal to or higher than the melting point.
  • the configuration of the side chain crystalline polymer of the present embodiment will be specifically described.
  • the side chain crystalline polymer of the present embodiment has a melting point.
  • the side chain crystalline polymer of this embodiment is crystallized at a temperature below the melting point, and exhibits phase transition at a temperature above the melting point to exhibit fluidity. That is, the side chain crystalline polymer of the present embodiment has temperature sensitivity that reversibly causes a crystalline state and a fluid state in response to a temperature change.
  • the melting point is a temperature at which a specific portion of the polymer that was initially aligned in an ordered arrangement becomes disordered by an equilibrium process, and is measured at 10 ° C./min by a differential thermal scanning calorimeter (DSC). It shall mean the value obtained by measurement.
  • the melting point of the side chain crystalline polymer of the present embodiment is not particularly limited, and is preferably higher than room temperature (23 ° C.), for example.
  • the melting point can be adjusted by changing the composition of the side chain crystalline polymer.
  • the weight average molecular weight of the side chain crystalline polymer of this embodiment is preferably larger than the weight average molecular weight of the crystalline macromonomer and 20,000 or less.
  • the lower limit of a weight average molecular weight is not specifically limited as long as the effect of this embodiment is acquired, It is preferable that it is 500 or more.
  • the weight average molecular weight is a value obtained by measuring the side chain crystalline polymer by gel permeation chromatography (GPC) and converting the obtained measurement value to polystyrene.
  • the structure of the side chain crystalline polymer of this embodiment is composed of a graft copolymer of a crystalline macromonomer and an amorphous monomer
  • the structure of the graft polymer represented by the general formula (I) described above is used. It is not limited.
  • the side chain crystalline polymer of this embodiment can also be used independently, without using it in combination with the acrylic pressure-sensitive adhesive mentioned later. When the side chain crystalline polymer of this embodiment is used alone, it is possible to provide a temperature-sensitive adhesive whose adhesive strength is reduced at a temperature lower than the melting point of the side chain crystalline polymer.
  • the crystalline macromonomer means a high molecular weight monomer having crystallinity and having a polymerizable double bond that can be polymerized with an amorphous monomer at one end.
  • the crystalline macromonomer in the present embodiment is a macromonomer represented by the above-described general formula (II) having a (meth) acrylic ester group at one end.
  • the carbon-carbon unsaturated bond in this (meth) acrylic acid ester group is a polymerizable double bond copolymerizable with an amorphous monomer.
  • R 1 representing a linear alkyl group having 16 or more carbon atoms functions as a crystalline site.
  • the weight average molecular weight of the crystalline macromonomer in this embodiment is preferably 10,000 or less. Although the lower limit of a weight average molecular weight is not specifically limited as long as the effect of this embodiment is acquired, It is preferable that it is 400 or more.
  • the weight average molecular weight is a value obtained by measuring a crystalline macromonomer by GPC and converting the obtained measurement value into polystyrene.
  • the configuration of the crystalline macromonomer of this embodiment is a high molecular weight monomer having a plurality of predetermined linear alkyl groups and having a polymerizable double bond capable of being polymerized with an amorphous monomer at one end. As long as it is not limited to the structure represented by the general formula (II) described above.
  • Non-crystalline monomer examples include (meth) acrylate having a C 1-12 alkyl group, a polar monomer, a reactive polysiloxane compound, vinyl acetate, styrene, and the like.
  • the non-crystalline monomer in the present embodiment is at least one selected from (meth) acrylates having a C 1-12 alkyl group, polar monomers, reactive polysiloxane compounds, vinyl acetate and styrene. Is preferred.
  • (meth) acrylate shall mean a methacrylate or an acrylate.
  • Examples of the (meth) acrylate having an alkyl group having 1 to 12 carbon atoms include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, and the like. You may use these 1 type or in mixture of 2 or more types. Of these examples, those having high cohesive strength are desirable in order to suppress a decrease in adhesive strength when the temperature rises. Specific examples include methyl acrylate. Therefore, it is preferable that the non-crystalline monomer contains at least methyl acrylate.
  • polar monomers include ethylene unsaturated monomers having a carboxyl group such as (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl ( Examples thereof include ethylenically unsaturated monomers having a hydroxyl group such as (meth) acrylate and 2-hydroxyhexyl (meth) acrylate. You may use these 1 type or in mixture of 2 or more types.
  • the reactive polysiloxane compound means a polysiloxane compound having a reactive functional group and having a siloxane bond in the main chain.
  • the functional group showing reactivity include a group having an ethylenically unsaturated double bond such as vinyl group, allyl group, (meth) acryl group, (meth) acryloyl group and (meth) acryloxy group; epoxy group (glycidyl) Group and an epoxycycloalkyl group), mercapto group, carbinol group, carboxyl group, silanol group, phenol group, amino group, hydroxyl group and the like.
  • These functional groups may be introduced into the side chain of the main chain, or may be introduced into both ends or one end of the main chain. That is, there are four types of reactive polysiloxane compounds, so-called side chain type, double-ended type, single-ended type, and double-ended side chain type, depending on the bonding position of the functional group to be introduced.
  • One end type that is, a one end reactive polysiloxane compound is preferable.
  • the one-terminal reactive polysiloxane compound include a modified polydimethylsiloxane compound represented by the following general formula (III).
  • R 5 represents an alkyl group.
  • R 6 represents a group: CH 2 ⁇ CHCOOR 7 — or CH 2 ⁇ C (CH 3 ) COOR 7 — (wherein R 7 represents an alkylene group).
  • r represents an integer of 5 to 200.
  • examples of the alkyl group represented by R 5 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, and pentyl.
  • straight-chain or branched alkyl groups having 1 to 6 carbon atoms such as a group, isopentyl group, neopentyl group, and hexyl group.
  • Examples of the alkylene group represented by R 7 include straight chain having 1 to 6 carbon atoms such as methylene group, ethylene group, trimethylene group, methylethylene group, propylene group, tetramethylene group, pentamethylene group, hexamethylene group, and the like. Examples include branched alkylene groups.
  • modified polydimethylsiloxane compound represented by the general formula (III) include compounds represented by the following general formula (IIIa). [Wherein R 5 , R 7 and r are the same as those in formula (III). ]
  • modified polydimethylsiloxane compound a commercially available product can be used. Specific examples thereof include, for example, single-end reactive silicone oils “X-22-2404” and “X-24” manufactured by Shin-Etsu Chemical Co., Ltd. -8201 ",” X-22-174DX “,” X-22-2426 “and the like.
  • Examples of the crystalline monomer (IV) include (meth) acrylate having a linear alkyl group having 16 or more carbon atoms, preferably 16 to 50 carbon atoms, more preferably 16 to 22 carbon atoms.
  • Examples of the (meth) acrylate having a linear alkyl group having 16 or more carbon atoms include cetyl (meth) acrylate, stearyl (meth) acrylate, eicosyl (meth) acrylate, and behenyl (meth) acrylate. You may use these 1 type or in mixture of 2 or more types.
  • the linear alkyl group having 16 or more carbon atoms in the (meth) acrylate described above corresponds to R 1 .
  • Other monomers are not particularly limited as long as they are copolymerizable with the crystalline monomer (IV), and are the same as those exemplified as the amorphous monomer from the viewpoint of compatibility with the amorphous monomer. Is preferred. You may use these 1 type or in mixture of 2 or more types.
  • the polymerization ratio of the crystalline monomer (IV) and other monomers is not particularly limited, and is preferably 90 to 100 parts by weight of the crystalline monomer (IV) and 0 to 10 parts by weight of the other monomers.
  • chain transfer agent (V) in this embodiment mercaptoethanol is used, but is not limited thereto. Any chain transfer agent (V) may be used as long as it can introduce a hydroxyl group into the prepolymer (VI). Thiol compounds having a hydroxyl group such as mercaptocyclohexanol and mercaptophenol can be used.
  • the amount of chain transfer agent (V) to be used is usually 0.1 to 25 parts by weight, preferably 3 to 15 parts by weight, based on 100 parts by weight of the total amount of the crystalline monomer (IV) and other monomers.
  • the polymerization reaction of the prepolymer (VI) may be performed without a solvent or in a polymerization solvent.
  • the polymerization solvent include aromatic hydrocarbons such as toluene and xylene; aliphatic esters such as ethyl acetate and butyl acetate; alicyclic hydrocarbons such as cyclohexane; and aliphatic hydrocarbons such as hexane and pentane. Etc. You may use these 1 type or in mixture of 2 or more types. What is necessary is just to determine the usage-amount of a polymerization solvent suitably.
  • the polymerization temperature of the prepolymer (VI) is usually 20 to 200 ° C, preferably 40 to 120 ° C.
  • the polymerization time is usually 1 to 24 hours, preferably 1 to 7 hours.
  • the reaction pressure is not particularly limited, and may be normal pressure (atmospheric pressure), reduced pressure, or increased pressure.
  • the polymerization reaction is desirably performed in an inert gas atmosphere such as nitrogen gas.
  • a polymerization initiator may be used.
  • the polymerization initiator include azo polymer polymerization initiators such as 2,2′-azobisisobutyronitrile and 2,2′-azobis (2,4-dimethylvaleronitrile); bezoyl peroxide, dimethyl ethyl ketone Examples thereof include organic peroxides such as peroxide and lauryl peroxide.
  • azo polymer polymerization initiator commercially available products can be used. Specifically, as the azo polymer polymerization initiator, both “ABN-R” and “ABN” manufactured by Nippon Hydrazine Kogyo Co., Ltd. can be used.
  • the functionalizing agent (VII) of this embodiment is di (meth) acrylic anhydride. Therefore, the crystalline macromonomer (II) of this embodiment is obtained by converting the crystalline monomer (IV) containing (meth) acrylate having a linear alkyl group having at least 16 carbon atoms into a chain transfer agent (V) having a hydroxyl group.
  • a prepolymer (VI) having a hydroxyl group at one end with a functionalizing agent (VII), which is a di (meth) acrylic anhydride, obtained by radical polymerization in the presence of And a macromonomer having a linear alkyl group having 16 or more carbon atoms represented by R 1 in the side chain and having a polymerizable double bond capable of being polymerized with an amorphous monomer at one end.
  • a functionalizing agent VII
  • functional grouping agent (VII) although di (meth) acrylic acid anhydride is used, it is not limited to this. That is, the functionalizing agent (VII) reacts with the hydroxyl group of the prepolymer (VI) to form a crystalline macromonomer (II) having a polymerizable double bond polymerizable with an amorphous monomer at one end. If it can do, it will not be limited to acid anhydrides, such as di (meth) acrylic acid anhydride.
  • the amount of the functionalizing agent (VII) used is not particularly limited, but is preferably larger than the amount of chain transfer agent (V) used, and is 1 in molar ratio to the amount of chain transfer agent (V) used. More preferably, it is 0.05 times to 1.1 times.
  • the remaining functionalizing agent (VII) is preferably removed by reacting with water or the like.
  • the reaction using the prepolymer (VI) as the crystalline macromonomer (II) can be carried out in a solvent.
  • a solvent the same thing as what was illustrated as a polymerization solvent of prepolymer (VI) is mentioned, for example. What is necessary is just to determine the usage-amount of a polymerization solvent suitably.
  • the reaction temperature in which the prepolymer (VI) is the crystalline macromonomer (II) is usually 50 to 150 ° C., preferably 50 to 130 ° C.
  • the reaction time is usually 10 minutes to 8 hours, preferably 30 minutes to 4 hours.
  • the reaction pressure is not particularly limited, and may be normal pressure (atmospheric pressure), reduced pressure, or increased pressure.
  • a polymerization inhibitor may be used. Moreover, it may replace with use of a polymerization inhibitor and may bubble mixed air, and may use these together.
  • the manufacturing method of crystalline macromonomer (II) is not limited to the reaction formula mentioned above as long as crystalline macromonomer (II) is obtained.
  • side chain crystalline polymer (I) the side chain crystalline polymer represented by the general formula (I) described above (hereinafter referred to as “side chain crystalline polymer (I)”) This will be described in detail with reference to an example of manufacturing.
  • the side chain crystalline polymer (I) is produced by a macromonomer method in which the above-described crystalline macromonomer (II) is copolymerized with the amorphous monomers (VIII, IX). Get.
  • a crystalline macromonomer (II) is copolymerized via a polymerizable double bond in a copolymer (a trunk part) of an amorphous monomer (VIII, IX), thereby producing a crystalline macromonomer.
  • the residue of monomer (II) forms a branch.
  • the side chain crystalline polymer (I) which is a graft copolymer can be obtained efficiently.
  • the amorphous monomer (VIII, IX) of this embodiment is a (meth) acrylate having an alkyl group having 1 to 12 carbon atoms, but is not limited thereto.
  • the polymerization ratio of the crystalline macromonomer (II) is preferably 10 to 90 parts by weight, and more preferably 20 to 80 parts by weight.
  • the polymerization ratio of the amorphous monomer (VIII, IX) is preferably 10 to 90 parts by weight, more preferably 20 to 80 parts by weight.
  • the polymerization reaction of the graft copolymer may be performed without a solvent or in a polymerization solvent. It does not specifically limit as a polymerization solvent, The same thing as what was illustrated as a polymerization solvent of prepolymer (VI) is mentioned. What is necessary is just to determine the usage-amount of a polymerization solvent suitably.
  • a chain transfer agent may be used to adjust the molecular weight distribution of the graft copolymer.
  • the chain transfer agent is not particularly limited, and examples thereof include sulfur-containing compounds such as dodecanethiol, thioglycolic acid, thioacetic acid, and mercaptoethanol; phosphorous acid compounds such as phosphorous acid and sodium phosphite; hypophosphorous acid And hypophosphite compounds such as sodium hypophosphite; alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, and n-butyl alcohol. You may use these 1 type or in mixture of 2 or more types. What is necessary is just to determine the usage-amount of a chain transfer agent suitably.
  • the polymerization temperature of the graft copolymer is usually 20 to 200 ° C, preferably 40 to 120 ° C.
  • the polymerization time is usually 1 to 24 hours, preferably 1 to 7 hours.
  • the reaction pressure is not particularly limited, and may be normal pressure (atmospheric pressure), reduced pressure, or increased pressure.
  • the polymerization reaction is desirably performed in an inert gas atmosphere such as nitrogen gas.
  • a polymerization initiator may be used. It does not specifically limit as a polymerization initiator, The same thing as what was illustrated as a polymerization initiator of prepolymer (VI) is mentioned. What is necessary is just to determine the usage-amount of a polymerization initiator suitably.
  • the manufacturing method of side chain crystalline polymer (I) is not limited to the reaction formula mentioned above as long as side chain crystalline polymer (I) is obtained.
  • the temperature-sensitive adhesive contains an acrylic pressure-sensitive adhesive and the above-described side chain crystalline polymer.
  • a temperature-sensitive adhesive means an adhesive whose adhesive force changes in response to a temperature change.
  • the temperature-sensitive adhesive of the present embodiment is a ratio at which the adhesive strength decreases when the side-chain crystalline polymer exhibits fluidity at a temperature higher than a preset switching temperature, that is, a temperature higher than the melting point of the side-chain crystalline polymer. And contains a side chain crystalline polymer. Therefore, if the temperature-sensitive adhesive of this embodiment is heated to a temperature equal to or higher than the melting point of the side-chain crystalline polymer, the side-chain crystalline polymer exhibits fluidity, thereby preventing the pressure-sensitive adhesive from sticking. Thereby, since adhesive force falls, a to-be-adhered member can be removed easily.
  • the side chain crystalline polymer is preferably blended at a ratio of 0.1 to 50 parts by weight with respect to 100 parts by weight of the acrylic pressure-sensitive adhesive, but is not limited thereto. That is, the side chain crystalline polymer is not limited to the exemplified composition as long as the initial adhesive strength of the temperature-sensitive adhesive is higher than 0 N / 25 mm, and can be blended in a desired ratio.
  • the temperature-sensitive adhesive of this embodiment has high transparency because it contains an acrylic pressure-sensitive adhesive that is compatible with the above-described side chain crystalline polymer trunk.
  • the monomer constituting the acrylic pressure-sensitive adhesive include alkyl groups having 1 to 12 carbon atoms such as ethylhexyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and the like.
  • (Meth) acrylate having a hydroxyalkyl group such as hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxyhexyl (meth) acrylate, and the like.
  • the weight average molecular weight of the acrylic pressure-sensitive adhesive is preferably 250,000 to 1,500,000.
  • the weight average molecular weight is a value obtained by measuring an acrylic pressure-sensitive adhesive with GPC and converting the obtained measurement value into polystyrene.
  • the method for producing the temperature sensitive adhesive is not particularly limited. To give a specific example, first, a side chain crystalline polymer is adjusted with a solvent to obtain a copolymer solution. Next, the monomers constituting the acrylic pressure-sensitive adhesive are polymerized to obtain an acrylic pressure-sensitive adhesive. Then, the copolymer solution and the pressure-sensitive adhesive are mixed to obtain a pressure-sensitive adhesive solution, and the obtained pressure-sensitive adhesive solution may be dried.
  • the polymerization method of the monomer constituting the acrylic pressure-sensitive adhesive is not particularly limited, and for example, a solution polymerization method, a bulk polymerization method, a suspension polymerization method, an emulsion polymerization method, and the like can be employed.
  • the monomer when the solution polymerization method is employed, the monomer can be polymerized by mixing the monomer constituting the acrylic pressure-sensitive adhesive with a solvent and stirring at about 40 to 90 ° C. for about 2 to 10 hours.
  • a well-known thing can be used as a solvent.
  • the temperature-sensitive adhesive of the present embodiment described above can be used as, for example, a substrate-less temperature-sensitive adhesive sheet.
  • the sheet is not limited to a sheet shape, and is a concept including a sheet shape or a film shape as long as the effects of the present embodiment are not impaired.
  • the thickness of the temperature-sensitive adhesive sheet is 1 to 500 ⁇ m, preferably 5 to 300 ⁇ m.
  • a release film is preferably laminated on the surface of the temperature-sensitive adhesive sheet. Examples of the release film include those obtained by applying a release agent such as silicone to the surface of a film made of polyethylene terephthalate or the like.
  • the temperature-sensitive adhesive of this embodiment can be used in the form of a tape, for example, in addition to the above-described baseless form.
  • the temperature-sensitive adhesive tape which concerns on one Embodiment of this invention is equipped with the base film and the adhesive layer which consists of the temperature-sensitive adhesive mentioned above laminated
  • the base film examples include synthetic resin films such as polyethylene, polyethylene terephthalate, polypropylene, polyester, polyamide, polyimide, polycarbonate, ethylene vinyl acetate copolymer, ethylene ethyl acrylate copolymer, ethylene polypropylene copolymer, and polyvinyl chloride. Is mentioned.
  • the base film may be composed of a single layer or a multilayer, and the thickness is usually about 5 to 500 ⁇ m.
  • the surface of the base film may be subjected to surface treatment such as corona discharge treatment, plasma treatment, blast treatment, chemical etching treatment, primer treatment, etc. in order to improve adhesion to the pressure-sensitive adhesive layer.
  • the thickness of the pressure-sensitive adhesive layer is 1 to 500 ⁇ m, preferably 5 to 300 ⁇ m.
  • the thickness and composition of the one-sided adhesive layer and the other-sided adhesive layer may be the same or different. Also good.
  • the other-side adhesive layer is not particularly limited as long as the one-sided adhesive layer is made of the above-described temperature-sensitive adhesive. Therefore, the pressure-sensitive adhesive layer on the other side can be constituted by, for example, a pressure-sensitive adhesive layer made of a pressure-sensitive adhesive.
  • the pressure-sensitive adhesive is a polymer having tackiness, and examples thereof include natural rubber adhesives, synthetic rubber adhesives, styrene / butadiene latex base adhesives, and acrylic adhesives.
  • a coating solution obtained by adding the above-described temperature-sensitive adhesive to a solvent may be applied to the surface of the substrate film and dried.
  • the coating can be generally performed with a knife coater, a roll coater, a calendar coater, a comma coater or the like. Further, depending on the coating thickness and the viscosity of the coating solution, a gravure coater, a rod coater or the like can be used.
  • a release film is preferably laminated on the surface of the pressure-sensitive adhesive layer, similarly to the temperature-sensitive pressure-sensitive adhesive sheet.
  • thermosensitive adhesive examples include, for example, touch panel bodies and liquid crystal covers in liquid crystal touch panels, as well as organic electroluminescence (organic EL), calculators, and personal computers. Examples include, but are not limited to, built-in electronic components, backlights and panel portions in liquid crystal panels.
  • crystalline macromonomer (II) ′ When the functionalizing agent (VII) ′ is used, the crystalline macromonomer represented by the general formula (II) ′ (hereinafter referred to as “crystalline macromonomer (II) ′”) as shown in the following reaction formula: There is.) [Wherein, R 1 and n are the same as those in formula (I). R 8 represents a hydrogen atom or a methyl group. m represents an integer of 1 to 9. ]
  • Crystalline macromonomer (II) ′ is a crystalline monomer (IV) containing (meth) acrylate having a linear alkyl group having at least 16 carbon atoms in the presence of a chain transfer agent (V) having a hydroxyl group.
  • a side chain obtained by reacting a prepolymer (VI) having a hydroxyl group at one end with a functionalizing agent (VII) ′, which is a (meth) acrylate having an isocyanato group, obtained by radical polymerization.
  • Is a macromonomer having a straight-chain alkyl group having 16 or more carbon atoms represented by R 1 and having a polymerizable double bond capable of being polymerized with an amorphous monomer at one end.
  • As the (meth) acrylate having an isocyanato group a commercially available product can be used. Specific examples thereof include “Karenz AOI” and “Karenz MOI” manufactured by Showa Denko K.K.
  • the amount of the (meth) acrylate having an isocyanato group is preferably 1.0 to 2.0 times in molar ratio to the amount of the chain transfer agent (V) having a hydroxyl group.
  • the molar ratio of the (meth) acrylate having an isocyanato group to the chain transfer agent (V) having a hydroxyl group ((meth) acrylate having an isocyanato group / chain transfer agent having a hydroxyl group) is 1.0 to It is preferably 2.0.
  • the adhesive physical properties tend to be improved.
  • the above-described molar ratio ((meth) acrylate having an isocyanato group / chain transfer agent having a hydroxyl group) is 1 More preferably, it is from 2 to 2.0, and even more preferably from 1.5 to 2.0.
  • a catalyst may be used.
  • the amount of the catalyst used is preferably 10 parts by weight or less with respect to 100 parts by weight in total of the prepolymer (VI) and the (meth) acrylate having an isocyanato group.
  • the catalyst examples include organotin compounds such as dibutyltin dilaurate, organometallic compounds such as bismuth catalyst and potassium catalyst.
  • organotin compounds such as dibutyltin dilaurate
  • organometallic compounds such as bismuth catalyst and potassium catalyst.
  • a commercially available catalyst can be used, and specific examples include, for example, “Pucat 25”, “Pucat B7”, “Pucat 15G” manufactured by Nippon Chemical Industry Co., Ltd.
  • the weight average molecular weight is a value obtained by measuring the copolymer with GPC and converting the obtained measurement value into polystyrene.
  • the melting point is a value measured using DSC under measurement conditions of 10 ° C./min.
  • Example 1 and Comparative Example A temperature-sensitive adhesive tape was prepared using the side chain crystalline polymer obtained in Synthesis Example 2 and Comparative Synthesis Example described above and the pressure-sensitive adhesive obtained in Synthesis Example 1, and the 180 ° peel strength was evaluated.
  • the production procedure and evaluation method of the temperature-sensitive adhesive tape are shown below, and the results are shown in Table 1.
  • the initial temperature (melting point of side chain crystalline polymer (hereinafter sometimes referred to as “Tm”) ⁇ 10) ° C. and (Tm + 10) ° C. and stainless steel plate at each atmospheric temperature 180 ° peel strength was measured according to JIS Z0237. Specifically, after the temperature-sensitive adhesive tape is attached to a stainless steel plate at an ambient temperature of 23 ° C. and the ambient temperature is adjusted to the measurement temperature, the temperature-sensitive adhesive tape is 180 ° at a speed of 300 mm / min with a load cell. It peeled. The initial temperature is 23 ° C.
  • the retention rate is a value calculated from the formula: [(Tm ⁇ 10) ° C. peel strength / initial temperature peel strength] ⁇ 100. ⁇ : 3N / 25mm or more and retention rate 70% or more ⁇ : Less than 3N / 25mm or retention rate 70%
  • the rate of decrease is a value calculated from the formula: ⁇ [Peel strength at (Tm-10) ° C. ⁇ Peel strength at (Tm + 10) ° C.] / Peel strength at (Tm ⁇ 10) ° C. ⁇ ⁇ 100.
  • ⁇ 0.5 N / 25 mm or less and a reduction rate of 80% or more ⁇ : More than 0.5 N / 25 mm or less than 80%
  • Example 1 showed a result that was superior in retention rate and higher in reduction rate than the comparative example. From this result, Example 1 can sufficiently maintain the initial adhesive strength (180 ° peel strength at the initial temperature) at a temperature lower than the melting point, and can sufficiently reduce the adhesive strength at a temperature higher than the melting point. I understand.
  • the molar ratio of 2-isocyanatoethyl acrylate to mercaptoethanol (2-isocyanatoethyl acrylate / mercaptoethanol) is 2.
  • the weight average molecular weight and melting point of the obtained copolymer, and the reaction rate of the prepolymer and 2-isocyanatoethyl acrylate estimated from 1 H-NMR are as follows. Weight average molecular weight: 4,200 Melting point: 58 ° C Reaction rate: 100%
  • the molar ratio of 2-isocyanatoethyl acrylate to mercaptoethanol (2-isocyanatoethyl acrylate / mercaptoethanol) is 1.5.
  • the weight average molecular weight and melting point of the obtained copolymer, and the reaction rate of the prepolymer and 2-isocyanatoethyl acrylate estimated from 1 H-NMR are as follows. Weight average molecular weight: 4,100 Melting point: 57 ° C Reaction rate: 100%
  • the molar ratio of 2-isocyanatoethyl acrylate to mercaptoethanol (2-isocyanatoethyl acrylate / mercaptoethanol) is 1.2.
  • the weight average molecular weight and melting point of the obtained copolymer, and the reaction rate of the prepolymer and 2-isocyanatoethyl acrylate estimated from 1 H-NMR are as follows. Weight average molecular weight: 4,000 Melting point: 57 ° C Reaction rate: 72%
  • the molar ratio of 2-isocyanatoethyl acrylate to mercaptoethanol (2-isocyanatoethyl acrylate / mercaptoethanol) is 1.
  • the weight average molecular weight and melting point of the obtained copolymer, and the reaction rate of the prepolymer and 2-isocyanatoethyl acrylate estimated from 1 H-NMR are as follows. Weight average molecular weight: 4,100 Melting point: 57 ° C Reaction rate: 56%
  • Example 2 A temperature-sensitive adhesive tape was produced using the pressure-sensitive adhesive obtained in Synthesis Example 1 in the same manner as in Example 1 except that the side chain crystalline polymer obtained in Synthesis Examples 3 to 7 was used. did. And 180 degree peel strength was evaluated like Example 1 mentioned above except having used the produced temperature sensitive adhesive tape. The results are shown in Table 2.

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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)
  • Macromonomer-Based Addition Polymer (AREA)
  • Graft Or Block Polymers (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne un polymère cristallin à chaîne latérale comprenant un macromonomère cristallin et un copolymère greffé d'un monomère non-cristallin. Un agent adhésif thermosensible selon la présente invention contient un agent de liaison sensible à la pression acrylique et le polymère cristallin à chaîne latérale et présente une force d'adhérence réduite aux températures situées au niveau ou au-dessus du point de fusion du polymère cristallin à chaîne latérale. Une feuille adhésive thermosensible selon la présente invention comprend l'agent adhésif thermosensible. Un ruban adhésif thermosensible selon la présente invention est pourvu d'un film formant substrat et d'une couche d'agent adhésif qui comprend l'agent adhésif thermosensible et qui est stratifiée sur au moins une surface du film formant substrat.
PCT/JP2015/059439 2014-04-04 2015-03-26 Polymère cristallin à chaîne latérale, agent adhésif thermosensible, feuille adhésive thermosensible et ruban adhésif thermosensible Ceased WO2015152006A1 (fr)

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JP2016511596A JP6695271B2 (ja) 2014-04-04 2015-03-26 側鎖結晶性ポリマー、感温性粘着剤、感温性粘着シートおよび感温性粘着テープ
KR1020167025294A KR102310619B1 (ko) 2014-04-04 2015-03-26 측쇄 결정성 폴리머, 감온성 점착제, 감온성 점착 시트 및 감온성 점착 테이프

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TWI779221B (zh) * 2018-07-27 2022-10-01 南韓商Ｌｇ化學股份有限公司 黏著劑組成物、包括其的黏著膜、包含黏著膜的背板膜以及塑膠有機發光顯示器
TWI779222B (zh) * 2018-07-27 2022-10-01 南韓商Ｌｇ化學股份有限公司 黏著劑組成物、包含其的黏著膜、以及包含黏著膜的背板膜及塑膠有機發光顯示器
JP2023011394A (ja) * 2021-07-12 2023-01-24 大日精化工業株式会社 活性エネルギー線硬化型（メタ）アクリレートポリマー、その製造方法、及びコーティング剤
US11993736B2 (en) 2018-07-27 2024-05-28 Lg Chem, Ltd. Adhesive composition, adhesive film comprising adhesive composition, back plate film comprising adhesive film, and plastic organic light emitting display comprising adhesive film
US11993734B2 (en) 2018-07-27 2024-05-28 Lg Chem, Ltd. Adhesive composition, adhesive film comprising same, backplate film comprising adhesive film, and plastic organic light-emitting display comprising adhesive film
US12006449B2 (en) 2018-07-27 2024-06-11 Lg Chem, Ltd. Adhesive composition, adhesive film comprising same, back plate film comprising adhesive film and plastic organic light-emitting display comprising adhesive film
US12006456B2 (en) 2018-07-27 2024-06-11 Lg Chem, Ltd. Adhesive composition, adhesion film comprising same, backplate film comprising adhesion film, and plastic organic light-emitting display comprising adhesion film
US12012535B2 (en) 2018-07-27 2024-06-18 Lg Chem, Ltd. Adhesive composition, adhesive film comprising same, backplate film comprising adhesive film, and plastic organic light emitting display comprising adhesive film
US12018188B2 (en) 2018-07-27 2024-06-25 Lg Chem, Ltd. Adhesive composition, adhesive film comprising same, backplate film comprising adhesive film, and plastic organic light emitting display comprising adhesive film

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JP6792509B2 (ja) * 2017-04-21 2020-11-25 ニッタ株式会社 感温性粘着剤
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JP2019143065A (ja) * 2018-02-22 2019-08-29 ニッタ株式会社 感温性粘着剤、感温性粘着シートおよび感温性粘着テープ
JP7037388B2 (ja) 2018-02-22 2022-03-16 ニッタ株式会社 感温性粘着剤、感温性粘着シートおよび感温性粘着テープ
US11993734B2 (en) 2018-07-27 2024-05-28 Lg Chem, Ltd. Adhesive composition, adhesive film comprising same, backplate film comprising adhesive film, and plastic organic light-emitting display comprising adhesive film
TWI779222B (zh) * 2018-07-27 2022-10-01 南韓商Ｌｇ化學股份有限公司 黏著劑組成物、包含其的黏著膜、以及包含黏著膜的背板膜及塑膠有機發光顯示器
US11993736B2 (en) 2018-07-27 2024-05-28 Lg Chem, Ltd. Adhesive composition, adhesive film comprising adhesive composition, back plate film comprising adhesive film, and plastic organic light emitting display comprising adhesive film
TWI779221B (zh) * 2018-07-27 2022-10-01 南韓商Ｌｇ化學股份有限公司 黏著劑組成物、包括其的黏著膜、包含黏著膜的背板膜以及塑膠有機發光顯示器
US12006449B2 (en) 2018-07-27 2024-06-11 Lg Chem, Ltd. Adhesive composition, adhesive film comprising same, back plate film comprising adhesive film and plastic organic light-emitting display comprising adhesive film
US12006456B2 (en) 2018-07-27 2024-06-11 Lg Chem, Ltd. Adhesive composition, adhesion film comprising same, backplate film comprising adhesion film, and plastic organic light-emitting display comprising adhesion film
US12012535B2 (en) 2018-07-27 2024-06-18 Lg Chem, Ltd. Adhesive composition, adhesive film comprising same, backplate film comprising adhesive film, and plastic organic light emitting display comprising adhesive film
US12018188B2 (en) 2018-07-27 2024-06-25 Lg Chem, Ltd. Adhesive composition, adhesive film comprising same, backplate film comprising adhesive film, and plastic organic light emitting display comprising adhesive film
US12018190B2 (en) 2018-07-27 2024-06-25 Lg Chem, Ltd. Adhesive composition, adhesive film comprising same, backplate film comprising adhesive film, and plastic organic light-emitting display comprising adhesive film
JP2023011394A (ja) * 2021-07-12 2023-01-24 大日精化工業株式会社 活性エネルギー線硬化型（メタ）アクリレートポリマー、その製造方法、及びコーティング剤
JP7637582B2 (ja) 2021-07-12 2025-02-28 大日精化工業株式会社 活性エネルギー線硬化型（メタ）アクリレートポリマー、その製造方法、及びコーティング剤

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