WO2013089091A1 - 硬化性樹脂組成物、硬化性樹脂成形体、硬化樹脂成形体及びそれらの製造方法、並びに積層体 - Google Patents
硬化性樹脂組成物、硬化性樹脂成形体、硬化樹脂成形体及びそれらの製造方法、並びに積層体 Download PDFInfo
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- WO2013089091A1 WO2013089091A1 PCT/JP2012/082051 JP2012082051W WO2013089091A1 WO 2013089091 A1 WO2013089091 A1 WO 2013089091A1 JP 2012082051 W JP2012082051 W JP 2012082051W WO 2013089091 A1 WO2013089091 A1 WO 2013089091A1
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- C08J2433/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2433/04—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2433/14—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2435/00—Characterised by the use of 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 a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
- C08J2435/02—Characterised by the use of homopolymers or copolymers of esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2439/00—Characterised by the use of 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
- C08J2439/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2481/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
- C08J2481/06—Polysulfones; Polyethersulfones
Definitions
- the present invention is a curable resin composition that is excellent in heat resistance, has a low residual amount of low-boiling substances, and has a small in-plane retardation, its production method, and a curable resin composition that is useful as a raw material for this curable resin molded article.
- the present invention relates to an article, a curable resin molded body, and a laminate having a layer made of a cured resin.
- displays such as liquid crystal displays and electroluminescence (EL) displays have used transparent plastic films instead of glass plates as substrates having electrodes in order to achieve thinning, weight reduction, flexibility, and the like. It is being considered.
- the transparent plastic film used for these applications is usually required to have heat resistance and a small in-plane retardation.
- melt extrusion methods and solution casting methods are known as methods for producing optical films.
- the solution casting method is expected as a method for producing an optical film because the in-plane retardation is small and a smooth film can be obtained.
- the solvent is difficult to volatilize, the amount of residual solvent in the resulting film is large, and the resulting film is likely to be curled. It was.
- Patent Document 1 discloses a method for producing a polyethersulfone film with less residual solvent by a solution casting method using a solution composition in which aromatic polyethersulfone is dissolved in a solvent containing 1,3-dioxolane. Is disclosed. However, in the Example of patent document 1, since it dries, heating temperature is raised continuously, there exists a problem of lengthening a drying process and has the subject that productivity is low.
- Patent Document 2 discloses a glass substitute resin composition having good chemical resistance and heat resistance, an amorphous thermoplastic resin such as polycarbonate and polyethersulfone, and bis (meta) curable with active energy rays.
- a resin composition containing an acrylate is described.
- the member obtained using this resin composition is described in the Example of patent document 2, the thickness is as much as 1 mm.
- this document exemplifies a thermoplastic resin having an aromatic ring such as polycarbonate or polyethersulfone as an amorphous thermoplastic resin, a resin composition containing a thermoplastic resin having these aromatic rings No examples of manufacture of materials and members using the resin composition are described.
- the present invention has been made in view of the above-described circumstances, and is a cured resin having excellent heat resistance, low residual amount of low-boiling substances such as solvents and curable monomers, and a small in-plane retardation. It aims at providing the laminated body which has a layer which consists of a curable resin composition and a curable resin molding useful as a raw material of a molded object, its manufacturing method, this cured resin molded object, and cured resin.
- thermoplastic resin having an aromatic ring in the molecule and having a glass transition temperature (Tg) of 140 ° C. or higher a curable monomer
- Tg glass transition temperature
- curable resin composition containing a photopolymerization initiator having an absorption band in the vicinity of 380 nm that is, having photopolymerization activity with respect to light having a wavelength of about 380 nm
- it has excellent heat resistance and low boiling point. It has been found that a cured resin molded body having a small amount of remaining product and a small in-plane retardation can be obtained.
- the film-shaped cured resin molding obtained using this curable resin composition forms a curable resin layer made of the curable resin composition on the process sheet, and then cures the curable resin layer. As a result, it was found that it can be obtained efficiently, and the present invention has been completed.
- thermoplastic resin (A) a curable monomer (B), and a photopolymerization initiator (C), wherein the thermoplastic resin (A) is present in the molecule. It is a thermoplastic resin having an aromatic ring and a glass transition temperature (Tg) of 140 ° C. or higher.
- Tg glass transition temperature
- the photopolymerization initiator (C) is measured with a 0.1% by mass acetonitrile solution, the absorbance at 380 nm is 0.
- a curable resin composition which is a photopolymerization initiator of 4 or more.
- the photopolymerization initiator (C) has the following formula
- R 8 represents a phenyl group which may have a substituent or an alkyl group having 1 to 10 carbon atoms which may have a substituent, and Ar has a substituent; Represents an aromatic group having 6 to 20 carbon atoms, m is an integer of 1 to 3, n is an integer of 0 to 2, and m + n is 3.
- the content of the thermoplastic resin (A) and the curable monomer (B) is a mass ratio of the thermoplastic resin (A) and the curable monomer (B), and the thermoplastic resin (A):
- the curable resin composition according to any one of (1) to (3), wherein the curable monomer (B) 3: 7 to 9: 1.
- thermoplastic resin (A) according to any one of (1) to (5), wherein the thermoplastic resin (A) is a thermoplastic resin selected from the group consisting of a polysulfone resin, a polyarylate resin, and a polycarbonate resin. Curable resin composition.
- the following curable resin molded articles (7) and (8) are provided.
- the cured resin moldings (9) and (10) below A cured resin molded product obtained by curing the curable resin molded product according to (7) or (8).
- the manufacturing method of the cured resin molding of following (10) and (11) is provided.
- Process 1 The process of forming the curable resin layer which consists of a curable resin composition containing a thermoplastic resin (A), a curable monomer (B), and a photoinitiator (C) on a process sheet.
- Step 2 A step of curing the curable resin layer obtained in Step 1 to form a cured resin layer (11)
- Step 2 is a step in which the amount of light in the range of 50 to 10,000 mJ / cm 2 is applied to the curable resin layer.
- the laminated body of following (13) is provided.
- (13) A laminate having at least one layer made of a cured resin obtained by curing the curable resin composition according to any one of (1) to (6).
- the curable resin composition of the present invention By using the curable resin composition of the present invention, it is possible to efficiently obtain a curable resin molded body, and by curing this curable resin molded body, it has excellent heat resistance, such as a solvent and an unreacted monomer. A cured resin molded body having a low residual amount of low-boiling substances and a small in-plane retardation can be obtained efficiently.
- the cured resin molded product (film-like product) of the present invention can be used as a layer constituting a laminate. This laminate can be suitably used as an electrode constituent material used for touch panels and the like, thin televisions, optical recording media, and optical sheet materials.
- the method for producing a cured resin molded body of the present invention it is possible to efficiently produce a cured resin molded body having excellent heat resistance, a low residual amount of low-boiling substances, and a small in-plane retardation.
- the cured resin molding of the present invention is a film-like product, it is excellent in heat resistance and has a low residual amount of low-boiling products, so curl is small and in-plane retardation is small. It is useful as a resin film for optical and electronic device members.
- the present invention is classified into 1) a curable resin composition, 2) a curable resin molded body, 3) a cured resin molded body, 4) a method for producing a cured resin molded body, and 5) a laminate. This will be described in detail.
- the curable resin composition of this invention is a curable resin composition containing a thermoplastic resin (A), a curable monomer (B), and a photoinitiator (C).
- the thermoplastic resin (A) is a thermoplastic resin having an aromatic ring in the molecule, a glass transition temperature (Tg) of 140 ° C. or higher, and the photopolymerization initiator (C) is 0.1% by mass. It is characterized by being a photopolymerization initiator having an absorbance at 380 nm of 0.4 or more when measured with an acetonitrile solution.
- the thermoplastic resin (A) used in the present invention is a thermoplastic resin having an aromatic ring in the molecule and a glass transition temperature (Tg) of 140 ° C. or higher.
- the aromatic ring of the thermoplastic resin (A) is not particularly limited, but is preferably a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, or an anthracene ring from the viewpoint of availability of raw materials, A biphenyl ring or a naphthalene ring is more preferable, and a benzene ring is particularly preferable.
- a thermoplastic resin having an aromatic ring a cured resin molded article having excellent heat resistance can be obtained.
- the glass transition temperature (Tg) of the thermoplastic resin (A) used in the present invention is 140 ° C. or higher, preferably 150 ° C. or higher.
- the upper limit of the glass transition temperature (Tg) is not particularly limited, but is usually 350 ° C. or lower.
- the glass transition temperature (Tg) refers to the temperature at the maximum point of tan ⁇ (loss elastic modulus / storage elastic modulus) obtained by viscoelasticity measurement.
- the thermoplastic resin (A) used in the present invention is preferably an amorphous thermoplastic resin.
- a cured resin molded article having excellent transparency can be obtained.
- an amorphous thermoplastic resin is excellent in the solubility with respect to an organic solvent, a cured resin molding can be efficiently formed using a solution casting method as described later.
- An amorphous thermoplastic resin refers to a thermoplastic resin whose melting point is not observed in differential scanning calorimetry.
- the weight average molecular weight (Mw) of the thermoplastic resin (A) is usually 8,000 to 3,000,000, preferably 10,000 to 2,000,000, more preferably 10,000 to 2,000.
- the molecular weight distribution (Mw / Mn) is preferably 1.0 to 5.0, more preferably 2.0 to 4.5.
- the weight average molecular weight (Mw) and the molecular weight distribution (Mw / Mn) are values in terms of polystyrene measured by a gel permeation chromatography (GPC) method.
- thermoplastic resin (A) examples include polysulfone resins, polyarylate resins, polycarbonate resins, and the like.
- the polysulfone resin is a polymer having a sulfone group (—SO 2 —) in the main chain.
- the polysulfone resin is not particularly limited, and known ones can be used. Examples thereof include resins made of a polymer compound having a repeating unit represented by the following (a) to (h).
- polyethersulfone resin (resin composed of a polymer compound having a repeating unit (a) above), polysulfone resin (resin composed of a polymer compound having a repeating unit (b) above), polyphenylsulfone Examples thereof include resins (resins composed of a polymer compound having the repeating unit (e) above).
- the polysulfone resin used in the present invention may be a modified polysulfone resin. Among these, as the polysulfone resin, a polyethersulfone resin or a polysulfone resin is preferable.
- the polyarylate resin is a resin made of a polymer compound obtained by a reaction between an aromatic diol and an aromatic dicarboxylic acid or a chloride thereof.
- the polyarylate resin is not particularly limited, and known ones can be used.
- the reaction method is not particularly limited, and may be any of a melt polymerization method, a solution polymerization method, and an interfacial polymerization method.
- aromatic diol examples include bis (4-hydroxyphenyl) methane [bisphenol F], bis (3-methyl-4-hydroxyphenyl) methane, 1,1-bis (4′-hydroxyphenyl) ethane, 1, 1-bis (3′-methyl-4′-hydroxyphenyl) ethane, 2,2-bis (4′-hydroxyphenyl) propane [bisphenol A], 2,2-bis (3′-methyl-4′-hydroxy) Bis (hydroxyphenyl) alkanes such as phenyl) propane, 2,2-bis (4′-hydroxyphenyl) butane, 2,2-bis (4′-hydroxyphenyl) octane; 1,1-bis (4′- Hydroxyphenyl) cyclopentane, 1,1-bis (4′-hydroxyphenyl) cyclohexane [bisphenol Z], 1,1-bi Bis (hydroxyphenyl) cycloalkanes such as (4′-hydroxyphenyl) -3,3,5-trimethylcyclohexane; bis (4-hydroxyphenyl) cycl
- Hydroxyphenyl) sulfides bis Bis (hydroxyphenyl) sulfoxides such as 4-hydroxyphenyl) sulfoxide and bis (3-methyl-4-hydroxyphenyl) sulfoxide; bis (4-hydroxyphenyl) sulfone [bisphenol S], bis (3-methyl-4- Bis (hydroxyphenyl) sulfones such as hydroxyphenyl) sulfone; bis (9,9-bis (4′-hydroxyphenyl) fluorene, bis (9′-methyl-4′-hydroxyphenyl) fluorene, etc. Hydroxyphenyl) fluorenes; and the like.
- aromatic dicarboxylic acid or chloride thereof examples include, for example, phthalic acid, isophthalic acid, terephthalic acid, 4,4′-biphenyldicarboxylic acid, diphenoxyethanedicarboxylic acid, diphenyl ether 4,4′-dicarboxylic acid, 4,4′- Examples thereof include diphenylsulfone dicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, and chlorides thereof.
- the polyarylate resin may be a modified polyarylate resin.
- a resin made of a polymer compound obtained by reaction of 2,2-bis (4′-hydroxyphenyl) propane and isophthalic acid is preferable.
- the polycarbonate resin is a polymer having a carbonate group (—O—C ( ⁇ O) —O—) in the main chain. It does not specifically limit as a polycarbonate-type resin, A well-known aromatic polycarbonate resin can be used.
- Aromatic polycarbonate resin is, for example, a method of reacting an aromatic diol and a carbonate precursor by an interfacial polycondensation method or a melt transesterification method, a method of polymerizing a carbonate prepolymer by a solid phase transesterification method, a cyclic carbonate compound It can be obtained by a method of polymerizing by ring-opening polymerization.
- thermoplastic resin (A) can be used individually by 1 type or in combination of 2 or more types.
- the curable monomer (B) is a monomer having a polymerizable unsaturated bond, and can be involved in the polymerization reaction or the polymerization reaction and the crosslinking reaction by the photopolymerization initiator (C). is there.
- “curing” means a broad concept including “monomer polymerization reaction” or “monomer polymerization reaction and subsequent polymer crosslinking reaction”.
- curable resin film when producing a film-like curable resin molded product (hereinafter sometimes referred to as “curable resin film”), by including a curable monomer, There is an effect of plasticizing the curable resin film.
- a curable resin film when a curable resin film is produced by a solution casting method or the like, the curable resin film is plasticized by containing the monofunctional curable monomer (B).
- the thermoplastic resin (A) having a high glass transition temperature (Tg) is used as in the present invention, normally, in the case of producing a film-like molded body, the problem of prolonged drying process. The problem of curling due to residual solvent tends to occur, but these problems can be solved by using the curable resin composition of the present invention containing the curable monomer (B).
- the molecular weight of the curable monomer (B) is preferably 3000 or less, more preferably 200 to 2000, and further preferably 200 to 1000.
- the number of polymerizable unsaturated bonds in the curable monomer (B) is not particularly limited, and may be a monofunctional monomer or a polyfunctional monomer. From the viewpoint of heat resistance, it is preferable to use a polyfunctional curable monomer because the heat resistance is improved by forming a crosslinked structure.
- the content of the polyfunctional curable monomer is preferably 40% by mass or more, more preferably 50 to 100% by mass, based on the total amount of the curable monomer (B).
- the polymerizable unsaturated bond is not particularly limited as long as it can participate in the curing reaction, but it is preferably present as a (meth) acryloyl group because of excellent reactivity.
- (meth) acryloyl group means both “acryloyl group” and “methacryloyl group”.
- a monofunctional (meth) acrylic acid derivative or a polyfunctional (meth) acrylic acid derivative can be preferably used as the curable monomer (B).
- the monofunctional (meth) acrylic acid derivative is not particularly limited, and a known compound can be used. Examples include (meth) acrylic acid derivatives having a nitrogen atom, (meth) acrylic acid derivatives having an alicyclic structure, (meth) acrylic acid derivatives having an ether structure, (meth) acrylic acid derivatives having an aromatic ring, and the like. It is done.
- a (meth) acrylic acid derivative having a nitrogen atom is preferable in that a cured resin molded product having further excellent heat resistance is obtained, and a (meth) acrylic acid derivative having an alicyclic structure is preferable in terms of optical properties.
- a (meth) acrylic acid derivative having a polyether structure is preferable from the viewpoint of toughness.
- Examples of the (meth) acrylic acid derivative having a nitrogen atom include any compound represented by the following formula.
- R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
- R 2 and R 3 each independently represent a hydrogen atom or an organic group having 1 to 12 carbon atoms
- R 2 and R 3 may combine to form a ring structure
- R 4 represents a divalent organic group.
- the alkyl group having 1 to 6 carbon atoms represented by R 1 include a methyl group, an ethyl group, and a propyl group, and a methyl group is preferable.
- Examples of the organic group having 1 to 12 carbon atoms represented by R 2 and R 3 include alkyl groups such as methyl group, ethyl group and propyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; phenyl group and biphenyl And aromatic groups such as a naphthyl group. These groups may have a substituent at any position.
- R 2 and R 3 may be combined to form a ring, and the ring may have a nitrogen atom or an oxygen atom in the skeleton.
- Examples of the divalent organic group represented by R 4 include groups represented by —NH— and —NH— (CH 2 ) p —.
- p is an integer of 1 to 10.
- N- (meth) acryloylmorpholine represented by the following formula is preferable.
- Examples of the (meth) acrylic acid derivative having an alicyclic structure include compounds represented by the following formula.
- R 1 represents the same meaning as described above, and R 5 is a group having an alicyclic structure.
- R 5 is a group having an alicyclic structure. Examples of the group having an alicyclic structure represented by R 5 include a cyclohexyl group, an isobornyl group, a 1-adamantyl group, a 2-adamantyl group, and a tricyclodecanyl group.
- (meth) acrylic acid derivative having an alicyclic structure examples include isobornyl (meth) acrylate, cyclohexyl (meth) acrylate, 1-adamantyl (meth) acrylate, 2-adamantyl (meth) acrylate and the like.
- Examples of the (meth) acrylic acid derivative having an ether structure include compounds represented by the following formula.
- R 1 represents the same meaning as described above, and R 6 represents an organic group having 1 to 12 carbon atoms.
- the organic group having 1 to 12 carbon atoms represented by R 6 include an alkyl group such as a methyl group, an ethyl group, and a propyl group; a cycloalkyl group such as a cyclopentyl group and a cyclohexyl group; a phenyl group, a biphenyl group, and a naphthyl group Aromatic groups such as groups; and the like.
- q represents an integer of 2 to 20.
- Specific examples of the (meth) acrylic acid derivative having an ether structure include ethoxylated o-phenylphenol (meth) acrylate and phenoxypolyethylene glycol (meth) acrylate.
- Examples of the (meth) acrylic acid derivative having an aromatic ring include benzyl (meth) acrylate.
- the polyfunctional (meth) acrylic acid derivative is not particularly limited, and a known compound can be used.
- a known compound can be used.
- the compound represented by the following formula is mentioned.
- R 1 represents the same meaning as described above, and R 7 represents a divalent organic group.
- R 7 represents a divalent organic group. Examples of the divalent organic group represented by R 7 include groups represented by the following formulas.
- s represents an integer of 1 to 20
- t represents an integer of 1 to 30, and u and v each independently represents an integer of 1 to 30.
- tricyclodecane dimethanol di (meth) acrylate 2-hydroxy-3-acryloyloxypropyl (meth) acrylate, polyethylene glycol di (meth) acrylate, propoxylated ethoxylated bisphenol A di (meth) acrylate Ethoxylated bisphenol A di (meth) acrylate, 1,10-decanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate and the like.
- bifunctional (meth) acrylic acid is easy to mix with the thermoplastic resin (A), and curling of the cured product can be suppressed because it is difficult to cause shrinkage due to curing.
- Derivatives are preferred.
- the bifunctional (meth) acrylic acid derivatives those in which the divalent organic group represented by R 7 in the above formula has a tricyclodecane skeleton are preferable in terms of heat resistance and toughness. Specific examples of such a compound include tricyclodecane dimethacrylate.
- a curable monomer (B) can be used individually by 1 type or in combination of 2 or more types.
- the content of the thermoplastic resin (A) and the curable monomer (B) contained in the curable resin composition is preferably a mass ratio of the thermoplastic resin (A) and the curable monomer (B).
- Is thermoplastic resin (A): curable monomer (B) 30: 70 to 90:10, more preferably 35:65 to 8: 2.
- thermoplastic resin (A): curable monomer (B) 30: 70
- the flexibility of the cured resin molded product May decrease.
- the photopolymerization initiator (C) is a photopolymerization initiator having an absorbance at 380 nm of 0.4 or more when measured with a 0.1% by mass acetonitrile solution.
- the absorbance is preferably 0.8 or more, more preferably 1.0 or more, and even more preferably 1.5 or more.
- it is usually 3.0 or less.
- the curable resin composition of the present invention contains the thermoplastic resin (A) having an aromatic ring.
- the aromatic ring in the thermoplastic resin (A) generally absorbs ultraviolet rays having a wavelength used for curing the curable resin, and thus inhibits the curing reaction. Since the curable resin composition of the present invention contains the photopolymerization initiator (C), the aromatic ring in the thermoplastic resin (A) is absorbed by using the photopolymerization initiator (C). The curing reaction can be initiated with light having a longer wavelength than the light to be emitted.
- the absorption edge on the long wavelength side of the wavelength absorbed by the aromatic ring in the thermoplastic resin (A) is 320 to 350 nm, the above photopolymerization having a large absorption at a wavelength longer than that (380 nm).
- the initiator (C) By using the initiator (C), the curing reaction can be initiated with long-wavelength light. Therefore, although the curable resin composition of this invention contains the thermoplastic resin (A) which has an aromatic ring, it can advance a curing reaction efficiently. For this reason, the curing reaction is sufficiently performed, and a cured resin molded body having high heat resistance can be obtained. Further, since it is not necessary to apply excessive energy to the resin, coloring of the cured resin molding can be avoided. Moreover, when it is set as a film-shaped cured resin molded body, curling does not occur.
- Examples of the photopolymerization initiator (C) include phosphorus-based polymerization initiators represented by the following formula.
- R 8 represents a phenyl group which may have a substituent or an alkyl group having 1 to 10 carbon atoms which may have a substituent, and Ar may have a substituent. It represents a good aromatic group having 6 to 20 carbon atoms.
- m represents an integer of 1 to 3
- n represents an integer of 0 to 2
- m + n is 3.
- m is 2 or more, two or more groups may be the same or different.
- n is 2, the two groups may be the same or different.
- Examples of the substituent for the phenyl group represented by R 8 include an alkyl group having 1 to 10 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, and an isopropyl group; and a carbon number of 3 such as a cyclopentyl group and a cyclohexyl group.
- Examples of the alkyl group having 1 to 10 carbon atoms represented by R 8 include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, and n-pentyl. Group, n-hexyl group and the like.
- Examples of the substituent for the alkyl group having 1 to 10 carbon atoms represented by R 8 include a cycloalkyl group having 3 to 10 carbon atoms such as a cyclopentyl group and a cyclohexyl group; a methoxy group, an ethoxy group, an n-propoxy group, And alkoxy groups having 1 to 10 carbon atoms such as isopropoxy group; aromatic groups such as phenyl group, biphenyl group and naphthyl group; halogen atoms such as fluorine atom and chlorine atom;
- Examples of the aromatic group having 6 to 20 carbon atoms that may have a substituent represented by Ar include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and anthranyl. Groups and the like. Of these, the aromatic group having 6 to 20 carbon atoms which may have a substituent represented by Ar is preferably a phenyl group. Examples of the substituent of the aromatic group having 6 to 20 carbon atoms that may have a substituent represented by Ar include those having 1 to 10 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
- photopolymerization initiator (C) examples include (2,4,6-trimethylbenzoyl) diphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, ethyl (2,4,6- Examples thereof include trimethylbenzoyl) phenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide.
- the photopolymerization initiator (C) As the photopolymerization initiator (C), a manufactured product can be used, but a commercially available product can also be used. Commercially available products include Irgacure 819, Irgacure 819DW, Irgacure 1870, Irgacure 1800, DAROCURE TPO, DAROCURE 4265 (above, manufactured by BASF) and SPEEDCURE TPO-L (produced by LAMBSON).
- a photoinitiator (C) can be used individually by 1 type or in combination of 2 or more types.
- the content of the photopolymerization initiator (C) contained in the curable resin composition is 0.05 to 15% by mass with respect to the total of the thermoplastic resin (A) and the curable monomer (B).
- the content is 0.1 to 10% by mass, and more preferably 0.3 to 5% by mass.
- 1.5 mass% or more is preferable with respect to a curable monomer (B), and, as for content of a photoinitiator (C), 2 mass% or more is more preferable.
- the photopolymerization initiator (C) By using the photopolymerization initiator (C) at such a ratio, it is possible to efficiently obtain a cured resin molded article that is superior in heat resistance, has a low residual amount of low-boiling substances, and has a smaller in-plane retardation. it can.
- the curable resin composition of this invention may contain a well-known thermal polymerization initiator and a photoinitiator other than said photoinitiator (C).
- the thermal polymerization initiator include organic peroxides and azo compounds.
- organic peroxides include dialkyl peroxides such as di-t-butyl peroxide, t-butylcumyl peroxide, and dicumyl peroxide; diacyl peroxides such as acetyl peroxide, lauroyl peroxide, and benzoyl peroxide ; Ketone peroxides such as methyl ethyl ketone peroxide, cyclohexanone peroxide, 3,3,5-trimethylcyclohexanone peroxide, methylcyclohexanone peroxide; peroxyketals such as 1,1-bis (t-butylperoxy) cyclohexane; T-butyl hydroperoxide, cumene hydroperoxide, 1,1,
- Photopolymerization initiators include 2,2-dimethoxy-1,2-diphenylethane-1-one, (1-hydroxycyclohexyl) phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1- [4- [4- (2-hydroxy-2 -Methyl-propionyl) -benzyl] phenyl] -2-methyl-propan-1-one, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethyl Amino-1- (4-morpholinophenyl) -butanone-1,2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholin ) Phenyl] -1-alkyl phenone photopolymerization initiator such
- polymerization initiators can be used singly or in combination of two or more.
- the polymerization initiator may be used in combination with triisopropanolamine or a photopolymerization initiation assistant such as 4,4′-diethylaminobenzophenone.
- the curable resin composition may contain other components as long as the objects and effects of the present invention are not impaired.
- examples of other components include a plasticizer, an antioxidant, and an ultraviolet absorber.
- the curable resin composition is prepared by, for example, mixing a thermoplastic resin (A), a curable monomer (B), a photopolymerization initiator (C) and other components as required, and an appropriate solvent as necessary. It can be prepared by dissolving or dispersing in.
- Curable resin molded product of the present invention is obtained from the curable resin composition of the present invention. It does not specifically limit as a shape of the curable resin molding of this invention, A film form, a sheet form, a rectangular parallelepiped shape etc. are mentioned. Especially, it is preferable that it is a film form or a sheet form. In the case of a film shape or a sheet shape, not only a long thing but a thing is also contained.
- a film-like molded body (curable resin film) can be produced, for example, by the solution casting method using the curable resin composition.
- the curable resin composition or a solution obtained by diluting the curable resin composition with an appropriate solvent
- the solvent may be removed by drying.
- the solvent to be used is not particularly limited as long as it can dissolve or disperse the thermoplastic resin (A) having an aromatic ring, the curable monomer (B), and the photopolymerization initiator (C).
- aliphatic hydrocarbon solvents such as n-hexane and n-heptane
- alicyclic hydrocarbon solvents such as cyclopentane and cyclohexane
- aromatic hydrocarbon solvents such as toluene and xylene
- methylene chloride, chloride Halogenated hydrocarbon solvents such as ethylene and dichloromethane
- alcohol solvents such as methanol, ethanol, propanol, butanol and propylene glycol monomethyl ether
- ketone solvents such as acetone, methyl ethyl ketone, 2-pentanone, isophorone and cyclohexanone
- ethyl acetate, And ester solvents such as butyl acetate
- the method for coating the curable resin composition on the process sheet is not particularly limited, and spin coating method, spray coating method, bar coating method, knife coating method, roll coating method, blade coating method, die coating method, gravure coating method.
- a known coating method such as the above can be used.
- the drying method of the obtained coating film is not particularly limited, and a curable resin film can be obtained using a conventionally known drying method such as hot air drying, hot roll drying, and infrared irradiation.
- the drying temperature of the coating film is usually 30 to 150 ° C., preferably 50 to 130 ° C., and the drying time is usually 30 seconds to 5 minutes, preferably 1 to 3 minutes.
- the curable resin composition of the present invention contains a thermoplastic resin (A) having a very high glass transition temperature (Tg), but contains a curable monomer (B). By doing so, the solvent can be efficiently removed.
- the thickness of the curable resin film is not particularly limited, and is usually 1 to 300 ⁇ m, preferably 2 to 200 ⁇ m, more preferably 3 to 100 ⁇ m.
- the curable resin composition of the present invention contains the curable monomer (B) having a plasticizing effect as described above, its glass transition temperature (Tg) is usually ⁇ 40 to 135 ° C., preferably Is -40 to 130.
- Tg glass transition temperature
- the curable resin composition of the present invention has a low glass transition temperature (Tg)
- the solvent is efficiently used in the drying step. Can be removed. For this reason, the cured resin molding with a small curl can be obtained by hardening the curable resin film of this invention.
- the cured resin molded body of the present invention is obtained by curing the curable resin molded body of the present invention.
- the curing method will be described in detail in the section of a method for producing a cured resin molded body described later.
- the shape of the cured resin molded body of the present invention is not particularly limited, and examples thereof include a film shape, a sheet shape, a pellet shape, and a rectangular parallelepiped shape. Especially, it is preferable that it is a film form or a sheet form. In the case of a film shape or a sheet shape, not only a long thing but a strip shape is also contained.
- the film-shaped or sheet-shaped one of the cured resin molded body of the present invention may be referred to as a cured resin film.
- the thickness of the cured resin molded body is not particularly limited and may be determined according to the purpose, but is usually 1 to 300 ⁇ m, preferably 2 to 200 ⁇ m, more preferably 3 to 100 ⁇ m.
- the cured resin molded body of the present invention has a glass transition temperature (Tg) of usually 140 ° C. or higher, preferably 150 ° C. or higher, and is excellent in heat resistance. If the glass transition temperature is 140 ° C. or higher, since the heat resistance is excellent, the laminate of the present invention described later is suitable for use in electronic devices.
- Tg glass transition temperature
- the cured resin molded article of the present invention is preferably colorless and transparent.
- a photoinitiator (C) can be utilized, a curing reaction is performed efficiently. For this reason, excessive light irradiation can be avoided, deterioration of resin can be suppressed, and a colorless and transparent cured resin molding can be obtained.
- the amount of light may be increased.
- a resin film such as a polyethylene terephthalate film that does not transmit light having a wavelength unnecessary for the curing reaction can be used.
- the cured resin film of the present invention contains a cured reaction product of a thermoplastic resin (A) and a curable monomer (B), and has a small in-plane retardation.
- the in-plane retardation of the cured resin film of the present invention is usually 20 nm or less, preferably 15 nm, more preferably 10 nm or less, and further preferably 5 nm or less. If the in-plane retardation is within the above range, it is suitable when the cured resin film of the present invention is used as an optical sheet material.
- the cured resin molding of the present invention is obtained by curing the curable resin composition of the present invention containing the photopolymerization initiator (C), the unreacted curable monomer (B) It does not remain and the heat resistance of the cured resin molding does not decrease.
- the mass reduction rate after 30 minutes at 150 ° C. of the cured resin molded body of the present invention is usually 2% or less, preferably 1.5% or less, and more preferably 1.0% or less. If the mass reduction rate is in the above range, curl does not occur in the film-shaped cured resin molded body of the present invention, which is suitable for use as an optical sheet material.
- the cured resin molded body of the present invention is obtained by utilizing a combination of the thermoplastic resin (A) and the curable monomer (B), and has excellent heat resistance and solvent residue.
- This is a cured resin molded body having a small in-plane retardation with little curling.
- the cured resin molded article of the present invention is obtained by utilizing a combination of a thermoplastic resin (A) and a photopolymerization initiator (C).
- an unreacted curable monomer ( B) does not remain. Therefore, it becomes a cured resin molding excellent in heat resistance.
- Method for producing cured resin molded body is not particularly limited, and a conventionally known method can be employed.
- the resulting molded product is irradiated by irradiating active energy rays and cured to form, and the curable resin composition is formed into a film by a solution casting method.
- the curable resin composition is formed into a film by a solution casting method.
- a film-shaped cured resin molded object (cured resin film)
- it can manufacture efficiently and can protect when the obtained cured resin film is preserve
- the cured resin film of the present invention has a process sheet because the handleability does not deteriorate even if the cured resin film is thin.
- Process 1 The process of forming the curable resin layer which consists of a curable resin composition containing a thermoplastic resin (A), a curable monomer (B), and a photoinitiator (C) on a process sheet.
- Step 2 A step of curing the curable resin layer obtained in Step 1 to form a cured resin layer
- a curable resin layer can be formed using the method described above in the curable resin molded article of the present invention.
- a curable resin composition containing a thermoplastic resin (A) and a curable monomer (B) (or a solution obtained by diluting a curable resin composition with an appropriate solvent) on a process sheet. Coating is performed, and the solvent is removed by drying to form a curable resin layer.
- the cured resin layer can be formed by curing the curable resin layer using the method described above in the cured resin molded body of the present invention.
- a photopolymerization initiator is contained in the curable resin composition, it is preferable to cure the curable resin layer by irradiating active energy rays.
- the active energy ray to be irradiated is preferably light having a wavelength of 200 to 400 nm, and more preferably light having a wavelength of 320 to 400 nm.
- the illuminance of the active energy ray to be irradiated is preferably 50 to 1000 mW / cm 2 .
- the amount of active energy rays to be irradiated is preferably 50 to 10,000 mJ / cm 2, more preferably 1000 to 10,000 mJ / cm 2 .
- the irradiation time is 0.1 to 1000 seconds, preferably 1 to 500 seconds, more preferably 10 to 100 seconds. In order to satisfy the above-mentioned light quantity in consideration of the heat load of the ultraviolet irradiation process, it is preferable to irradiate a plurality of times.
- the curable resin layer is irradiated with active energy rays through a filter that cuts light having a wavelength of 320 nm or less, and light having a wavelength necessary for the curing reaction. It is preferable to irradiate only. Thereby, since the light of the wavelength of 320 nm or less unnecessary for hardening reaction does not permeate
- resin films such as a polyethylene terephthalate film, can be utilized instead of this filter.
- the resin film may be laminated on the curable resin layer before step 2.
- the process sheet is usually peeled off in a predetermined process depending on the use of the cured resin film.
- the manufacturing method which has the said process 1 and 2 forms a cured resin film using a process sheet, even if the cured resin film obtained by this method has a process sheet. It may be good or not.
- the laminate of the present invention is a laminate having at least one layer made of a cured resin obtained by curing the curable resin composition of the present invention.
- the laminate of the present invention may have other layers.
- Other layers included in the laminate are not particularly limited, and examples thereof include a hard coat layer, a refractive index adjustment layer, an easy adhesion layer, a light diffusion layer, an antiglare treatment layer, a gas blocking layer, a transparent conductive layer, and a process. A sheet etc. are mentioned.
- the hard coat layer is a layer provided for the purpose of improving scratch resistance.
- the hard coat layer is obtained, for example, by forming a cured film on the surface of the cured resin film using a curable resin.
- the curable resin include ultraviolet curable resins such as silicon resins, urethane resins, acrylic resins, and epoxy resins.
- the refractive index adjustment layer is a layer provided for controlling reflection.
- the refractive index adjusting layer can be formed using a high refractive material or a low refractive material so as to obtain desired performance.
- the easy adhesion layer is a layer provided in order to improve the adhesion of the surface.
- the easy adhesion layer can be formed by a conventionally known method.
- the light diffusion layer is a layer provided for diffusing light, and can increase the viewing angle of a liquid crystal display device or the like.
- the light diffusion layer can be formed by a conventionally known method.
- the antiglare treatment layer is a layer provided for the purpose of preventing visual interference of transmitted light due to reflection of external light from the surface of the cured resin film.
- the antiglare treatment layer can be formed by a conventionally known method using a filler such as silica particles.
- the gas barrier layer is a layer having a characteristic of suppressing permeation of oxygen and water vapor. Examples of the gas barrier layer include a layer made of an inorganic vapor-deposited film, a layer containing a gas barrier resin, and a layer obtained by implanting ions into a layer containing a polymer compound.
- the transparent conductive layer is a transparent and conductive layer.
- the material for the transparent conductive layer include semiconductive metal oxides such as indium tin oxide (ITO) and zinc indium oxide (IZO).
- the transparent conductive layer can be formed by vapor deposition, sputtering, ion plating, thermal CVD, plasma CVD, or the like.
- seat is normally laminated
- a plastic film such as a polyethylene terephthalate film may be used as it is, or a sheet, a plastic film or the like coated with a release agent and provided with a release agent layer may be used.
- the thickness of the laminate of the present invention can be appropriately determined depending on the intended use of the electronic device, but from the viewpoint of handleability, the substantial thickness is preferably 1 to 300 ⁇ m, more preferably 2 to 200 ⁇ m. More preferably, it is 3 to 100 ⁇ m.
- the “substantial thickness” means the thickness in use. That is, the laminate of the present invention may have a process sheet or the like, but the thickness of a portion (process sheet or the like) removed during use is not included in the “substantial thickness”.
- the laminate of the present invention is suitably used as an electrode constituent material used for touch panels and the like, thin televisions, optical recording media, and optical sheet materials.
- a curable resin composition A is formed on a surface opposite to an easy adhesion layer of a polyethylene terephthalate (PET) film (Toyobo Co., Ltd., PET 50A-4100, thickness 50 ⁇ m) by a fountain die method, and the thickness after drying is Coating was performed to 50 ⁇ m, and the obtained coating film was dried by heating at 50 ° C. for 2 minutes and then at 130 ° C. for 2 minutes to obtain a curable resin film A with a process sheet.
- PET polyethylene terephthalate
- a PET film (Toyobo Co., Ltd., PET50A-4100, thickness 50 ⁇ m) is laminated on the curable resin film A to cut light with a wavelength of 320 nm or less, and a belt conveyor type ultraviolet irradiation device (Igraphics) ECS-401GX), UV lamp height 150mm, UV lamp output 3kw (converted output 120mW / cm), light intensity 365nm with high pressure mercury lamp (IGraphics H04-L41) Was 271 mW / cm 2 , and the amount of light was 500 mJ / cm 2 (ultraviolet light meter: UV-351, manufactured by Oak Manufacturing Co., Ltd.).
- Igraphics ultraviolet irradiation device
- the ultraviolet ray was irradiated twice under the conditions of an ultraviolet lamp height of 150 mm, an illuminance of a light wavelength of 365 nm of 271 mW / cm 2 , and an amount of light of 1,000 mJ / cm 2 , and a cured resin film with a process sheet A was obtained.
- the total amount of ultraviolet light was 2,500 mJ / cm 2 .
- the sample from which the PET film was peeled was used as a sample.
- Examples 2 to 6 Comparative Example 1
- Curable resin compositions B to G were prepared in the same manner as in Example 1 except that the blending ratios shown in Table 1 were changed.
- cured resin films B to G with a process sheet were obtained in the same manner as in Example 1.
- Polymerization initiator 1 bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide [manufactured by BASF, Irgacure 819 (absorbance at 380 nm in 0.1% acetonitrile solution: 1.9)]
- Polymerization initiator 2 (2,4,6-trimethylbenzoyl) diphenylphosphine oxide [manufactured by BASF, DAROCURE TPO (absorbance at 380 nm in 0.1% acetonitrile solution: 1.6)]
- Polymerization initiator 3 Ethyl (2,4,6-trimethylbenzoyl) phenylphosphine oxide [manufactured by LAMBSON, SPEEDCURE TPO-L (absorbance at 380 nm in 0.1% acetonitrile solution: 1.6)]
- Polymerization initiator 4 A mixture of bis (2,6-dimethoxybenzoyl) -2,
- PET film PET50A-4100, manufactured by Toyobo Co., Ltd., thickness 50 ⁇ m
- PET50A-4100 polyethylene terephthalate film
- the film was applied and dried by heating at 50 ° C. for 2 minutes and then at 130 ° C. for 2 minutes to produce a film.
- Glass transition temperature (Tg) Glass transition temperature (Tg)
- TTA viscoelasticity measuring instrument
- Tg glass transition temperature
- the cured resin films A to F obtained in Examples 1 to 6 are all films having a small in-plane retardation. Further, since the cured resin films A to F have a small mass reduction rate and curl value, it is considered that the solvent is almost removed in the drying process. Further, as can be seen from the high glass transition temperature, the cured resin films A to F are excellent in heat resistance. On the other hand, the comparative example 1 which does not use a photoinitiator (C) is considered that curing reaction is not enough, and the glass transition temperature of the cured resin film G is a low value. The film produced by the melt extrusion method obtained in Comparative Example 2 had a large in-plane retardation.
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Abstract
Description
これらの用途に用いられる透明プラスチックフィルムは、通常、耐熱性を有し、面内位相差が小さいことが求められる。
また、溶液キャスト法により、ガラス転移温度が高い樹脂を用いてフィルムを製造する場合、溶媒が揮発しにくく、得られるフィルムの残留溶媒量が多く、得られるフィルムにカールが生じやすいという問題があった。
しかしながら、特許文献1の実施例では、加熱温度を連続的に昇温しながら乾燥を行うため、乾燥工程の長時間化の問題があり、生産性が低いという課題を抱えている。
(1)熱可塑性樹脂(A)、硬化性単量体(B)、及び光重合開始剤(C)を含有する硬化性樹脂組成物であって、熱可塑性樹脂(A)が、分子内に芳香環を有する、ガラス転移温度(Tg)が140℃以上の熱可塑性樹脂であり、光重合開始剤(C)が、0.1質量%のアセトニトリル溶液で測定した際の、380nmにおける吸光度が0.4以上の光重合開始剤であることを特徴とする、硬化性樹脂組成物。
(2)熱可塑性樹脂(A)が、非晶性熱可塑性樹脂である、(1)に記載の硬化性樹脂組成物。
(3)光重合開始剤(C)が、下記式
(4)熱可塑性樹脂(A)と硬化性単量体(B)の含有量が、熱可塑性樹脂(A)と硬化性単量体(B)の質量比で、熱可塑性樹脂(A):硬化性単量体(B)=3:7~9:1である、(1)~(3)のいずれかに記載の硬化性樹脂組成物。
(5)光重合開始剤(C)の含有量が、熱可塑性樹脂(A)と硬化性単量体(B)の合計に対して、0.05~15質量%である、(1)~(4)のいずれかに記載の硬化性樹脂組成物。
(6)熱可塑性樹脂(A)が、ポリスルホン系樹脂、ポリアリレート系樹脂、及びポリカーボネート系樹脂からなる群から選択される熱可塑性樹脂である、(1)~(5)のいずれかに記載の硬化性樹脂組成物。
(7)(1)~(6)のいずれかに記載の硬化性樹脂組成物を成形して得られる、硬化性樹脂成形体。
(8)フィルム状物である、(7)に記載の硬化性樹脂成形体。
(9)(7)又は(8)に記載の硬化性樹脂成形体を硬化させることで得られる硬化樹脂成形体。
本発明の第4によれば、下記(10)、(11)の硬化樹脂成形体の製造方法が提供される。
(10)以下の工程1及び2を有する、(9)に記載の硬化樹脂成形体の製造方法。
工程1:工程シート上に、熱可塑性樹脂(A)、硬化性単量体(B)、及び光重合開始剤(C)を含有する硬化性樹脂組成物からなる硬化性樹脂層を形成する工程
工程2:工程1で得られた硬化性樹脂層を硬化させて、硬化樹脂層を形成する工程
(11)工程2が、硬化性樹脂層に50~10,000mJ/cm2の範囲の光量の活性エネルギー線を照射することで、前記硬化性樹脂層を硬化させる工程である、(10)に記載の硬化樹脂成形体の製造方法。
(12)工程2が、320nm以下の波長の光をカットするフィルターを介して、前記硬化性樹脂層に活性エネルギー線を照射することを特徴とする、(11)に記載の硬化樹脂成形体の製造方法。
(13)前記(1)~(6)のいずれかに記載の硬化性樹脂組成物を硬化して得られる硬化樹脂からなる層を少なくとも1層有する積層体。
本発明の硬化樹脂成形体(フィルム状物)は、積層体を構成する層として用いることができる。この積層体はタッチパネル等に用いられる電極構成材料や、薄型テレビ、光記録メディア、光学シート材料として好適に用いることができる。
本発明の硬化樹脂成形体の製造方法によれば、耐熱性に優れ、低沸点物の残存量が少なく、面内位相差が小さい硬化樹脂成形体を効率よく製造することができる。
特に、本発明の硬化樹脂成形体がフィルム状物の場合には、耐熱性に優れ、かつ、低沸点物の残存量が少ないものであるため、カールが少なく、しかも面内位相差が小さいため、光学用や電子デバイス部材用の樹脂フィルムとして有用である。
本発明の硬化性樹脂組成物は、熱可塑性樹脂(A)、硬化性単量体(B)、及び光重合開始剤(C)を含有する硬化性樹脂組成物であって、熱可塑性樹脂(A)が、分子内に芳香環を有する、ガラス転移温度(Tg)が140℃以上の熱可塑性樹脂であり、光重合開始剤(C)が、0.1質量%のアセトニトリル溶液で測定した際の、380nmにおける吸光度が0.4以上の光重合開始剤であることを特徴とする。
本発明に用いる熱可塑性樹脂(A)は、分子内に芳香環を有する、ガラス転移温度(Tg)が140℃以上の熱可塑性樹脂である。
熱可塑性樹脂(A)が有する芳香環としては、特に限定はないが、原料の入手容易性の観点から、ベンゼン環、ビフェニル環、ナフタレン環、ターフェニル環、又はアントラセン環が好ましく、ベンゼン環、ビフェニル環、又はナフタレン環がより好ましく、ベンゼン環が特に好ましい。
芳香環を有する熱可塑性樹脂を用いることで、耐熱性に優れる硬化樹脂成形体を得ることができる。
本明細書において、ガラス転移温度(Tg)は、粘弾性測定により得られたtanδ(損失弾性率/貯蔵弾性率)の最大点の温度をいう。
これらの中でも、ポリスルホン系樹脂としては、ポリエーテルスルホン樹脂又はポリスルホン樹脂が好ましい。
これらの中でも、ポリアリレート系樹脂としては、2,2-ビス(4’-ヒドロキシフェニル)プロパンとイソフタル酸との反応により得られる高分子化合物からなる樹脂が好ましい。
ポリカーボネート系樹脂としては、特に限定されず、公知の芳香族ポリカーボネート樹脂が使用できる。
芳香族ポリカーボネート樹脂は、例えば、芳香族ジオールとカーボネート前駆体とを界面重縮合法や溶融エステル交換法で反応させる方法や、カーボネートプレポリマーを固相エステル交換法により重合させる方法、環状カーボネート化合物の開環重合法により重合させる方法によって得ることができる。
カーボネート前駆体としては、カルボニルハライド、カーボネートエステルまたはハロホルメート等が挙げられ、具体的にはホスゲン、ジフェニルカーボネートまたは二価フェノールのジハロホルメート等が挙げられる。
熱可塑性樹脂(A)は1種単独で、あるいは2種以上を組み合わせて用いることができる。
硬化性単量体(B)は、重合性不飽和結合を有する単量体であって、光重合開始剤(C)によって重合反応、又は、重合反応及び架橋反応に関与し得る単量体である。なお、本明細書において、「硬化」とは、この「単量体の重合反応」、又は、「単量体の重合反応及び引き続く重合体の架橋反応」を含めた広い概念を意味する。
硬化性単量体(B)中の重合性不飽和結合の数は特に制限されず、1官能型の単量体であっても、多官能型の単量体であってもよい。耐熱性の観点からは、架橋構造を形成することで耐熱性が向上するため、多官能型の硬化性単量体を用いることが好ましい。多官能型の硬化性単量体の含有量は、硬化性単量体(B)の全量中、40質量%以上が好ましく、50~100質量%がより好ましい。
単官能の(メタ)アクリル酸誘導体としては、特に限定されず、公知の化合物を用いることができる。例えば、窒素原子を有する(メタ)アクリル酸誘導体、脂環式構造を有する(メタ)アクリル酸誘導体、エーテル構造を有する(メタ)アクリル酸誘導体、芳香環を有する(メタ)アクリル酸誘導体等が挙げられる。
なかでも、窒素原子を有する(メタ)アクリル酸誘導体は、耐熱性にさらに優れる硬化樹脂成形体が得られる点で好ましく、脂環式構造を有する(メタ)アクリル酸誘導体は、光学特性の点で好ましく、ポリエーテル構造を有する(メタ)アクリル酸誘導体は、靭性の点で好ましい。
R1で表される炭素数1~6のアルキル基としては、メチル基、エチル基、プロピル基等が挙げられ、メチル基が好ましい。
R2及びR3で表される炭素数1~12の有機基としては、メチル基、エチル基、プロピル基等のアルキル基;シクロペンチル基、シクロへキシル基等のシクロアルキル基;フェニル基、ビフェニル基、ナフチル基等の芳香族基;が挙げられる。これらの基は、任意の位置に置換基を有していてもよい。また、R2とR3が一緒になって環を形成してもよく、該環は、骨格中に窒素原子や酸素原子を有していてもよい。
R4で表される2価の有機基としては、-NH-、-NH-(CH2)p-で表される基が挙げられる。ここで、pは、1~10の整数である。
R5で表される脂環式構造を有する基としては、シクロへキシル基、イソボルニル基、1-アダマンチル基、2-アダマンチル基、トリシクロデカニル基等が挙げられる。
エーテル構造を有する(メタ)アクリル酸誘導体の具体例としては、エトキシ化o-フェニルフェノール(メタ)アクリレート、フェノキシポリエチレングリコール(メタ)アクリレート等が挙げられる。
具体的には、トリシクロデカンジメタノールジ(メタ)アクリレート、2-ヒドロキシ-3-アクリロイロキシプロピル(メタ)クリレート、ポリエチレングリコールジ(メタ)アクリレート、プロポキシ化エトキシ化ビスフェノールAジ(メタ)アクリレート、エトキシ化ビスフェノールAジ(メタ)アクリレート、1,10-デカンジオールジ(メタ)アクリレート、1,6-ヘキサンジオールジ(メタ)アクリレート等が挙げられる。
また、2官能(メタ)アクリル酸誘導体のなかでも、耐熱性と靭性という点から、上記式において、R7で表される2価の有機基がトリシクロデカン骨格を有するものが好ましい。このような化合物としては、具体的には、トリシクロデカンジメタクリレートが挙げられる。
硬化性樹脂組成物に含まれる、熱可塑性樹脂(A)と硬化性単量体(B)の含有量は、熱可塑性樹脂(A)と硬化性単量体(B)の質量比で、好ましくは、熱可塑性樹脂(A):硬化性単量体(B)=30:70~90:10、より好ましくは、35:65~8:2である。
熱可塑性樹脂(A)と硬化性単量体(B)をこのような割合で含有する硬化性樹脂組成物を用いることで、耐熱性により優れ、低沸点物の残存量が少なく、かつ、より面内位相差が小さい硬化樹脂成形体を得ることができる。
硬化性樹脂組成物に含まれる硬化性単量体(B)の含有量が、熱可塑性樹脂(A):硬化性単量体(B)=30:70を超えると、硬化樹脂成形体の柔軟性が低下するおそれがある。
一方、硬化性樹脂組成物に含まれる硬化性単量体(B)の含有量が、熱可塑性樹脂(A):硬化性単量体(B)=90:10未満だと、可塑化効果が得られず、残留溶媒が増加するおそれがある。
光重合開始剤(C)は、0.1質量%のアセトニトリル溶液で測定した際の、380nmにおける吸光度が0.4以上の光重合開始剤である。
硬化反応を効率よく進行させることができるという点から、上記吸光度は0.8以上が好ましく、1.0以上がより好ましく、1.5以上がさらに好ましい。また、上限値は特にないが、通常は、3.0以下である。
熱可塑性樹脂(A)中の芳香環は、一般に硬化性樹脂を硬化させるために利用される波長の紫外線を吸収するため、硬化反応を阻害する原因となる。本発明の硬化性樹脂組成物は、上記の光重合開始剤(C)を含有するので、かかる光重合開始剤(C)を利用することにより、熱可塑性樹脂(A)中の芳香環が吸収する光よりも長波長の光で硬化反応を開始させることができる。
具体的には、熱可塑性樹脂(A)中の芳香環が吸収する波長の長波長側の吸収端は、320~350nmであるため、それ以上の波長(380nm)で吸収が大きい上記の光重合開始剤(C)を用いることで、長波長の光で硬化反応を開始させることができる。
したがって、本発明の硬化性樹脂組成物は、芳香環を有する熱可塑性樹脂(A)を含有するものであるが、硬化反応を効率よく進行させることができる。このため、硬化反応が十分行われ、耐熱性の高い硬化樹脂成形体を得ることができる。また、樹脂に過剰のエネルギーを加えずにすむため、硬化樹脂成形体の着色も避けられる。また、フィルム状の硬化樹脂成形体とした場合に、カールを生じることもない。
mが2以上のとき、2つ以上の基は同一であっても、異なっていてもよく、nが2のとき、2つの基は同一であっても、異なっていてもよい。
R8で表される炭素数1~10のアルキル基の置換基としては、シクロペンチル基、シクロへキシル基等の炭素数3~10のシクロアルキル基;メトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基等の炭素数1~10のアルコキシル基;フェニル基、ビフェニル基、ナフチル基等の芳香族基;フッ素原子、塩素原子等のハロゲン原子;等が挙げられる。
Arで表される置換基を有していてもよい炭素数6~20の芳香族基の置換基としては、メチル基、エチル基、n-プロピル基、イソプロピル基等の炭素数1~10のアルキル基;シクロペンチル基、シクロへキシル基等の炭素数1~10のシクロアルキル基;メトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基等の炭素数1~5のアルコキシル基;フッ素原子、塩素原子等のハロゲン原子;等が挙げられる。
硬化性樹脂組成物に含まれる、光重合開始剤(C)の含有量は、熱可塑性樹脂(A)と硬化性単量体(B)の合計に対して、0.05~15質量%が好ましく、0.1~10質量%がより好ましく、0.3~5質量%がさらに好ましい。
また、光重合開始剤(C)の含有量は、硬化性単量体(B)に対して、1.5質量%以上が好ましく、2質量%以上がより好ましい。
光重合開始剤(C)をこのような割合で用いることにより、耐熱性により優れ、低沸点物の残存量が少なく、かつ、より面内位相差が小さい硬化樹脂成形体を効率よく得ることができる。
熱重合開始剤としては、有機過酸化物やアゾ系化合物が挙げられる。
有機過酸化物としては、ジ-t-ブチルパーオキサイド、t-ブチルクミルパーオキサイド、ジクミルパーオキサイド等のジアルキルパーオキサイド類;アセチルパーオキサイド、ラウロイルパーオキサイド、ベンゾイルパーオキサイド等のジアシルパーオキサイド類;メチルエチルケトンパーオキサイド、シクロヘキサノンパーオキサイド、3,3,5-トリメチルシクロヘキサノンパーオキサイド、メチルシクロヘキサノンパーオキサイド等のケトンパーオキサイド類;1,1-ビス(t-ブチルパーオキシ)シクロヘキサン等のパーオキシケタール類;t-ブチルヒドロパーオキサイド、クメンヒドロパーオキサイド、1,1,3,3-テトラメチルブチルヒドロパーオキサイド、p-メンタンヒドロパーオキサイド、ジイソプロピルベンゼンヒドロパーオキサイド、2,5-ジメチルヘキサン-2,5-ジヒドロパーオキサイド等のヒドロパーオキサイド類;t-ブチルパーオキシアセテート、t-ブチルパーオキシ-2-エチルヘキサノエート、t-ブチルパーオキシベンゾエート、t-ブチルパーオキシイソプロピルカーボネート等のパーオキシエステル類;等が挙げられる。
アゾ系化合物としては、2,2’-アゾビス(4-メトキシ-2,4-ジメチルバレロニトリル)、2,2’-アゾビス(2-シクロプロピルプロピオニトリル)、2,2’-アゾビス(2,4-ジメチルバレロニトリル)、アゾビスイソブチロニトリル、2,2’-アゾビス(2-メチルブチロニトリル)、1,1’-アゾビス(シクロヘキサン-1-カルボニトリル)、2-(カルバモイルアゾ)イソブチロニトリル、2-フェニルアゾ-4-メトキシ-2,4-ジメチルバレロニトリル等が挙げられる。
また、重合開始剤は、トリイソプロパノールアミンや、4,4’-ジエチルアミノベンゾフェノン等の光重合開始助剤等を併用して用いてもよい。
硬化性樹脂組成物は、例えば、熱可塑性樹脂(A)、硬化性単量体(B)、光重合開始剤(C)及び所望により他の成分を混合し、必要に応じて、適当な溶媒に溶解又は分散させることにより調製することができる。
本発明の硬化性樹脂成形体は、本発明の硬化性樹脂組成物から得られるものである。本発明の硬化性樹脂成形体の形状としては、特に限定されず、フィルム状、シート状、直方体状等が挙げられる。中でも、フィルム状又はシート状であることが好ましい。フィルム状又はシート状の場合、長尺のものに限らず、のものも含まれる。
得られた塗膜の乾燥方法は特に制限されず、熱風乾燥、熱ロール乾燥、赤外線照射等、従来公知の乾燥方法を利用して、硬化性樹脂フィルムを得ることができる。
硬化性樹脂フィルムの厚みは、特に制限されず、通常、1~300μm、好ましくは2~200μm、より好ましくは、3~100μmである。
本発明の硬化樹脂成形体は、本発明の硬化性樹脂成形体を硬化させることで得られるものである。硬化方法については、後述する硬化樹脂成形体の製造方法の項で詳述する。
ガラス転移温度が140℃以上であれば、耐熱性に優れるため、後述する本発明の積層体が電子デバイスの用途に用いられる場合に好適である。
また、硬化反応の効率をさらに上げたい場合、光量を上げればよいが、この場合は、活性エネルギー線照射装置にフィルターを取付けて、硬化反応に必要な波長の光のみを照射することが好ましい。また、このフィルターの代わりに、硬化反応に不要な波長の光を透過させないポリエチレンテレフタレートフィルム等の樹脂フィルムを利用することができる。
面内位相差が上記範囲内であれば、本発明の硬化樹脂フィルムを光学シート材料として用いる場合に好適である。
質量減少率が上記の範囲であれば、本発明のフィルム状の硬化樹脂成形体にカールが生じることがなく、光学シート材料として用いる場合に好適である。
また、本発明の硬化樹脂成形体は、熱可塑性樹脂(A)と光重合開始剤(C)の組み合わせを利用して得られるものであり、この組み合わせにより、未反応の硬化性単量体(B)が残留することがなくなる。したがって、耐熱性に優れる硬化樹脂成形体になる。
る。
本発明の硬化樹脂成形体を製造する方法は特に制限されず、従来公知の方法を採用することができる。例えば、硬化性樹脂組成物を押出成形した後、得られた成形物に活性エネルギー線等を照射して、硬化させることにより成形する方法、硬化性樹脂組成物を溶液キャスト法によってフィルム状の成形物を得た後、得られたフィルム状の成形物に、活性エネルギー線等を照射して、硬化させることにより成形する方法等が挙げられるが、面内の位相差は低減されることができるという点から、後者の方法が好ましい。
工程1:工程シート上に、熱可塑性樹脂(A)、硬化性単量体(B)、及び光重合開始剤(C)を含有する硬化性樹脂組成物からなる硬化性樹脂層を形成する工程
工程2:工程1で得られた硬化性樹脂層を硬化させて、の硬化樹脂層を形成する工程
例えば、工程シート上に、熱可塑性樹脂(A)、硬化性単量体(B)を含有する硬化性樹脂組成物(又は硬化性樹脂組成物を適当な溶媒で希釈して得られる溶液)を塗工し、溶媒を乾燥除し、硬化性樹脂層を形成する。
例えば、硬化性樹脂組成物に光重合開始剤が含まれる場合は、活性エネルギー線を照射することで、硬化性樹脂層を硬化させることが好ましい。
照射する活性エネルギー線の照度は、50~1000mW/cm2であることが好ましい。照射する活性エネルギー線の光量は、50~10,000mJ/cm2が好ましく、1000~10,000mJ/cm2であることがより好ましい。
照射時間は、0.1~1000秒、好ましくは1~500秒、更に好ましくは10~100秒である。紫外線照射工程の熱負荷を考慮して前述の光量を満たすために、複数回照射することが好ましい。
また、このフィルターの代わりに、ポリエチレンテレフタレートフィルム等の樹脂フィルムを利用することができる。
樹脂フィルムを利用する場合、工程2の前に、硬化性樹脂層上に樹脂フィルムを積層すればよい。
以上の方法により、工程シート付硬化樹脂フィルムを得ることができる。
本発明の積層体は、本発明の硬化性樹脂組成物を硬化して得られる硬化樹脂からなる層を少なくとも1層有する積層体である。
本発明の積層体は、他の層を有していてもよい。積層体に含まれる、その他の層としては、特に限定されず、例えば、ハードコート層、屈折率調整層、易接着層、光拡散層、防眩処理層、ガス遮断層、透明導電層、工程シート等が挙げられる。
屈折率調整層は、反射を制御するために設ける層である。屈折率調整層、所望の性能が得られるように、高屈折材料や低屈折材料を用いて形成することができる。
易接着層は、表面の接着性を向上させるために設ける層である。易接着層は、従来公知の方法により形成することができる。
光拡散層は、光を拡散させるために設ける層であり、液晶表示装置等の視野角を拡大することができる。光拡散層は、従来公知の方法により形成することができる。
防眩処理層は、硬化樹脂フィルム表面から外光が反射することによる透過光の視認妨害を防止すること等を目的に設けられる層である。防眩処理層は、シリカ粒子等のフィラーを用いて、従来公知の方法により形成することができる。
ガス遮断層は、酸素や水蒸気の透過を抑制する特性を有する層である。ガス遮断層は、無機蒸着膜からなる層、ガス遮断性樹脂を含む層、高分子化合物を含む層にイオンを注入して得られる層等が挙げられる。これらのガス遮断層は、公知の方法により形成することができる。
透明導電層は、透明で導電性を有する層である。透明導電層の材料としては、酸化インジウムスズ(ITO)や酸化亜鉛インジウム(IZO)等の半導電性金属酸化物が挙げられる。透明導電層は、蒸着法、スパッタリング法、イオンプレーティング法、熱CVD法、プラズマCVD法等により形成することができる。
工程シートは、通常、硬化樹脂フィルムの最外層に積層され、硬化樹脂フィルムを保存、運搬等する際に保護する役割を有し、所定の工程において剥離されるものである。工程シートとしては、ポリエチレンテレフタレートフィルムのようなプラスチックフィルムをそのまま用いてもよく、紙やプラスチックフィルム等に剥離剤を塗布し剥離剤層を設けたものを用いてもよい。
なお、「実質的な厚み」とは、使用状態における厚みをいう。すなわち、本発明の積層体は、工程シート等を有していてもよいが、使用時に除去される部分(工程シート等)の厚みは、「実質的な厚み」には含まれない。
ポリアリレート系樹脂(PAR)のペレット(ユニチカ社製、Uポリマー P-1001A、Tg=195℃)60質量部をジクロロメタンに溶解して15質量%溶液を調製し、次いで、N-アクリロイルモルホリン(興人社製、ACMO)39質量部、ビス(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキサイド(BASF社製、Irgacure819)1質量部を混合して、硬化性樹脂組成物Aを調製した。
次に、硬化性樹脂フィルムA上に、320nm以下の波長の光をカットするためにPETフィルム(東洋紡績社製、PET50A-4100、厚み50μm)を積層し、ベルトコンベア式紫外線照射装置(アイグラフィクス社製、ECS-401GX)を使用し、高圧水銀ランプ(アイグラフィクス社製、H04-L41)にて、紫外線ランプ高さ150mm、紫外線ランプ出力3kw(換算出力120mW/cm)、光線波長365nmの照度が271mW/cm2、光量が500mJ/cm2(紫外線光量計:株式会社オーク製作所社製、UV-351)となる条件で紫外線照射を行った。さらに同紫外線照射装置を使用し、紫外線ランプ高さ150mm、光線波長365nmの照度が271mW/cm2、光量が1,000mJ/cm2の条件で2回紫外線照射を行ない、工程シート付硬化樹脂フィルムAを得た。紫外線の総光量は、2,500mJ/cm2であった。なお、以下の測定においては、PETフィルムを剥がしたものをサンプルとして用いた。
第1表に記載の配合割合に変更したことを除き、実施例1と同様の方法により、硬化性樹脂組成物B~Gを調製した。硬化性樹脂組成物B~Gを用いて、実施例1と同様の方法により、工程シート付硬化樹脂フィルムB~Gを得た。
〔熱可塑性樹脂〕
PAR:ポリアリレート系樹脂(ユニチカ社製、Uポリマー P-1001A、Tg=195℃)
PES:ポリエーテルスルホン系樹脂(BASF社製、ULTRASON E 2010、Tg=225℃)
PSF:ポリスルホン系樹脂(BASF社製、ULTRASON S 3010、Tg=180℃)
PC:ポリカーボネート系樹脂(出光興産社製、タフロン LS1700、Tg=145℃)
〔単官能単量体〕
ACMO:N-アクリロイルモルホリン(興人社製)
ALEN:エトキシ化o-フェニルフェノールアクリレート(新中村化学工業社製、A-LEN-10)
〔多官能単量体〕
ADCP:トリシクロデカンジメタノールジアクリレート(新中村化学工業社製、ADCP)
ABE:エトキシ化ビスフェノールAジアクリレート(新中村化学工業社製、ABE-300)
重合開始剤1:ビス(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキサイド〔BASF社製、Irgacure 819 (0.1%アセトニトリル溶液中における380nmにおける吸光度:1.9)〕
重合開始剤2:(2,4,6-トリメチルベンゾイル)ジフェニルホスフィンオキサイド〔BASF社製、DAROCURE TPO (0.1%アセトニトリル溶液中における380nmにおける吸光度:1.6)〕
重合開始剤3:エチル(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキサイド〔LAMBSON社製、SPEEDCURE TPO-L(0.1%アセトニトリル溶液中における380nmにおける吸光度:1.6)〕
重合開始剤4:ビス(2,6-ジメトキシベンゾイル)-2,4,4-トリメチルペンチルフォスフィンオキサイドと1-(ヒドロキシシクロヘキシル)フェニルケトンの混合物〔BASF社製、Irgacure 1800(0.1%アセトニトリル溶液中における380nmにおける吸光度:0.4)〕
重合開始剤5:1-(ヒドロキシシクロヘキシル)フェニルケトン〔BASF社製、Irgacure 184(0.1%アセトニトリル溶液中における380nmにおける吸光度:0.1)〕
ポリアリレート系樹脂のペレット(ユニチカ社製、Uポリマー P-1001A、Tg=195℃)を用いて、溶融押出し法により、厚み50μmのフィルムを作製した。
(比較例3)
ポリアリレート系樹脂のペレット(ユニチカ社製、Uポリマー P-1001A、Tg=195℃)をジクロロメタンに溶解して15重量%溶液を調製した。
工程シートとしてポリエチレンテレフタレート(PET)フィルム(東洋紡社製、PET50A-4100、厚み50μm)の易接着層と反対の面上に、上記溶液をファウンテンダイ方式で、乾燥後の厚みが50μmになるように塗布し、得られた塗膜を50℃で2分間、次いで130℃で2分間加熱することで乾燥して、フィルムを作製した。
実施例及び比較例で得られた工程シート付硬化樹脂フィルムA~Gから工程シートを剥離したものを用いて、面内位相差を測定した。
測定は、位相差測定装置(王子計測機器社製、「KOBRA-WR」)を用いて、23℃にて測定した。光波長は589nmにて行った。結果を第1表に示す。
なお、第1表には、比較例2、3で得られたフィルムの面内位相差を合わせて示す。
実施例及び比較例で得られた工程シート付硬化樹脂フィルムA~Gから工程シートを剥離したものの、溶剤や硬化性単量体等の低沸点物の残存量を評価するために、示差熱熱重量同時測定装置(TG/DTA)(SHIMAZU社製、DTG-60)を用いて、20mgの試料を150℃で30分放置したときの質量減少率を測定した。結果を第1表に示す。
なお、第1表には、比較例2、3で得られたフィルムの質量減少率を合わせて示す。
実施例及び比較例で得られた工程シート付硬化樹脂フィルムA~Gから工程シートを剥離下もののカールの程度を評価するために、平面上に100mm×100mmの硬化樹脂フィルムA~Gをそれぞれ置き、そのときのフィルムの角の高さ(mm)をそれぞれ測定した。4つの角の値を合計して、カールの程度(mm)を評価した。結果を第1表に示す。
なお、第1表には、比較例2、3で得られたフィルムの値を合わせて示す。
実施例及び比較例で得られた、工程シート付硬化性樹脂フィルムA~G、及び工程シート付硬化樹脂フィルムA~Gから工程シートを剥離したものを用いて、粘弾性測定機器(ティー・エイ・インスツルメント社製、商品名DMA Q800)を使用し、周波数11Hz、昇温3℃/分で0~250℃の範囲で引張モードによる粘弾性を測定した。この測定で得られたtanδ(損失弾性率/貯蔵弾性率)の最大点における温度をガラス転移温度(Tg)とした。結果を第1表に示す。
第1表には、比較例2、3で得られたフィルムのガラス転移温度(Tg)も示す。
一方、光重合開始剤(C)を使用しない比較例1は、硬化反応が十分でないと考えられ、硬化樹脂フィルムGのガラス転移温度が低い値になっている。
比較例2で得られる、溶融押出法で作製したフィルムは、面内位相差が大きかった。
また、比較例3で得られる、溶液キャスト法のみで作製したフィルムは、溶剤の除去が十分でないと考えられ、質量減少率とカールの値が大きくなっている。また、硬化性単量体(B)の反応生成物を含まないことから、面内位相差が大きくなっている。
Claims (13)
- 熱可塑性樹脂(A)、硬化性単量体(B)、及び光重合開始剤(C)を含有する硬化性樹脂組成物であって、
熱可塑性樹脂(A)が、分子内に芳香環を有する、ガラス転移温度(Tg)が140℃以上の熱可塑性樹脂であり、
光重合開始剤(C)が、0.1質量%のアセトニトリル溶液で測定した際の、380nmにおける吸光度が0.4以上の光重合開始剤であることを特徴とする、硬化性樹脂組成物。 - 熱可塑性樹脂(A)が、非晶性熱可塑性樹脂である、請求項1に記載の硬化性樹脂組成物。
- 熱可塑性樹脂(A)と硬化性単量体(B)の含有量が、熱可塑性樹脂(A)と硬化性単量体(B)の質量比で、熱可塑性樹脂(A):硬化性単量体(B)=3:7~9:1である、請求項1~3のいずれかに記載の硬化性樹脂組成物。
- 光重合開始剤(C)の含有量が、熱可塑性樹脂(A)と硬化性単量体(B)の合計に対して、0.05~15質量%である、請求項1~4のいずれかに記載の硬化性樹脂組成物。
- 熱可塑性樹脂(A)が、ポリスルホン系樹脂、ポリアリレート系樹脂、及びポリカーボネート系樹脂からなる群から選択される熱可塑性樹脂である、請求項1~5のいずれかに記載の硬化性樹脂組成物。
- 請求項1~6のいずれかに記載の硬化性樹脂組成物を成形して得られる硬化性樹脂成形体。
- フィルム状物である、請求項7に記載の硬化性樹脂成形体。
- 請求項7又は8に記載の硬化性樹脂成形体を硬化させることで得られる硬化樹脂成形体。
- 以下の工程1及び2を有する、請求項9に記載の硬化樹脂成形体の製造方法。
工程1:工程シート上に、熱可塑性樹脂(A)、硬化性単量体(B)、及び光重合開始剤(C)を含有する硬化性樹脂組成物からなる硬化性樹脂層を形成する工程
工程2:工程1で得られた硬化性樹脂層を硬化させて、硬化樹脂層を形成する工程 - 工程2が、硬化性樹脂層に50~10,000mJ/cm2の範囲の光量の活性エネルギー線を照射することで、前記硬化性樹脂層を硬化させる工程である、請求項10に記載の硬化樹脂成形体の製造方法。
- 工程2が、320nm以下の波長の光をカットするフィルターを介して、前記硬化性樹脂層に活性エネルギー線を照射することを特徴とする、請求項11に記載の硬化樹脂成形体の製造方法。
- 請求項1~6のいずれかに記載の硬化性樹脂組成物を硬化して得られる硬化樹脂からなる層を少なくとも1層有する積層体。
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