Classifications

• • 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
  • C08F290/06—Polymers provided for in subclass C08G
  • C08F290/067—Polyurethanes; Polyureas
• • 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
  • C08F2/00—Processes of polymerisation
  • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
• • 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
  • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
  • C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
• • 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
  • C08F290/06—Polymers provided for in subclass C08G
• • 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
  • C08F30/00—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
  • C08F30/02—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/13—Phenols; Phenolates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/13—Phenols; Phenolates
  • C08K5/134—Phenols containing ester groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/55—Boron-containing compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L33/00—Compositions 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; Compositions of derivatives of such polymers
  • C08L33/04—Homopolymers or copolymers of esters
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
  • C08L43/02—Homopolymers or copolymers of monomers containing phosphorus
• • 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
  • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16

Definitions

• This disclosure relates to polymerizable compositions, etc.
• Patent Document 1 describes a thermosetting composition that contains a polymerizable compound.
• a phosphorus compound is used as a component of the polymerizable composition.
• a phosphorus compound it is also necessary to lower the reaction initiation temperature.
• One aspect of the present disclosure aims to provide a polymerizable composition that contains a phosphorus compound and that is capable of lowering the reaction initiation temperature.
• a polymerizable composition that contains a phosphorus compound and that is capable of lowering the reaction initiation temperature.
• the numerical range indicated by “ ⁇ ” indicates a range including the numerical values described before and after “ ⁇ ” as the minimum and maximum values, respectively.
• “A or more” in the numerical range means a range exceeding A and A.
• “A or less” in the numerical range means a range less than A and A.
• the upper limit or lower limit of a numerical range of a certain stage can be arbitrarily combined with the upper limit or lower limit of a numerical range of another stage.
• the upper limit or lower limit of the numerical range may be replaced with a value shown in the examples.
• “A or B” may include either A or B, or may include both.
• the materials exemplified in this specification may be used alone or in combination of two or more types.
• the content of each component in the composition means the total amount of the multiple substances present in the composition, unless otherwise specified.
• (Meth)acrylate means at least one of acrylate and the corresponding methacrylate. The same applies to other similar expressions such as “(meth)acrylic”.
• the content of (meth)acrylate compounds means the total amount of acrylate compounds and methacrylate compounds.
• the "alkyl group” may be linear, branched, or cyclic unless otherwise specified.
• the "hydroxy group” does not include the OH group contained in the carboxy group.
• total mass of the polymerizable composition refers to the total mass of the solid content of the polymerizable composition.
• the solid content of the polymerizable composition refers to the non-volatile content excluding volatile content (water, organic solvent, etc.) that can be volatilized.
• the solid content refers to the components that remain without volatilization when the polymerizable composition is dried, and includes components that are liquid, syrup-like, wax-like, etc. at 25°C.
• the "weight average molecular weight” can be measured by gel permeation chromatography (GPC) under the following measurement conditions, and converted from a calibration curve using standard polystyrene.
• GPC gel permeation chromatography
• Apparatus Tosoh Corporation, GPC-8020 Detector: Tosoh Corporation, RI-8020 Column: Gelpack GL-A-160-S + GL-A150, manufactured by Resonac Corporation Sample concentration: 120 mg/3 mL Solvent: Tetrahydrofuran Injection volume: 60 ⁇ L Pressure: 294 x 106 Pa (30 kgf/ cm2 ) Flow rate: 1.00 mL/min
• component (A) a borate anion
• component (B) at least one selected from the group consisting of an aromatic carboxylic acid having two or more hydroxy groups, a salt of the aromatic carboxylic acid, and a hydrate of the aromatic carboxylic acid
• the polymerizable composition according to this embodiment contains at least one polymerizable compound, and may contain at least one polymerizable compound selected from the group consisting of a compound containing component (A), component (B), and component (C), or may contain a polymerizable compound other than at least one selected from the group consisting of a compound containing component (A), component (B), and component (C).
• the polymerizable composition according to this embodiment may contain a polymerizable compound other than at least one selected from the group consisting of a compound containing component (A), component (B), and component (C).
• the polymerizable composition according to this embodiment can be used as a thermosetting polymerizable composition.
• the polymerizable composition according to this embodiment can lower the reaction initiation temperature.
• the polymerizable composition according to this embodiment can achieve a reaction initiation temperature of, for example, 84.00°C or less (preferably, 80.00°C or less, 75.00°C or less, 70.00°C or less, 65.00°C or less, 60.00°C or less, etc.) in the evaluation method described in the examples below.
• the excellent storage stability with respect to the reaction initiation temperature means that it is possible to suppress an increase in the reaction initiation temperature when the polymerizable composition (e.g., a film-like polymerizable composition) is stored, and for example, it is possible to suppress an increase in the reaction initiation temperature when a film-like polymerizable composition is stored at 25°C for one day (24 hours).
• the polymerizable composition e.g., a film-like polymerizable composition
• a rate of change in the reaction initiation temperature of, for example, 50.00% or less (preferably, 40.00% or less, 30.00% or less, 20.00% or less, 10.00% or less, etc.).
• the polymerizable composition according to this embodiment it is possible to obtain excellent adhesive strength between adherends when a cured product of the polymerizable composition is interposed between the adherends.
• excellent adhesive strength can be obtained when a cured product of the polymerizable composition is interposed between a resin film (such as a polyimide film) and a glass plate.
• an adhesive strength of, for example, 3.0 N/cm or more preferably, 3.5 N/cm or more, 4.0 N/cm or more, 4.5 N/cm or more, 5.0 N/cm or more, 5.5 N/cm or more, etc.
• 3.0 N/cm or more preferably, 3.5 N/cm or more, 4.0 N/cm or more, 4.5 N/cm or more, 5.0 N/cm or more, 5.5 N/cm or more, etc.
• the polymerizable composition according to this embodiment are not particularly limited, and examples include display devices, semiconductor devices, and electronic device components.
• the polymerizable composition according to this embodiment may be used in micro LEDs (Light Emitting Diodes), micro OLEDs (Organic Light Emitting Diodes), and the like.
• the polymerizable composition according to this embodiment contains a borate anion as component (A).
• the polymerizable composition according to this embodiment may contain a boron salt containing a borate anion (a salt of component (A) and a counter cation of component (A); hereinafter referred to as "component (a1)").
• component (A) may be bonded to a counter cation, or may be free without being bonded to a counter cation.
• the number of boron atoms may be 1 to 4, 1 to 3, or 1 to 2, from the viewpoint of making it easier to lower the reaction initiation temperature.
• component (A) may contain a borate anion having a naphthalene ring (substituted or unsubstituted naphthyl group), may contain a borate anion having a naphthalene ring (substituted or unsubstituted naphthyl group) bonded to a boron atom, may contain at least one anion selected from the group consisting of an alkyltriarylborate anion and a tetraarylborate anion, may contain an alkyltriarylborate anion, may contain an alkyltrinaphthylborate anion, may contain a butyltrinaphthylborate anion, or may contain an n-butyltrinaphthylborate anion.
• the number of naphthalene rings (number in one molecule) or the number of naphthalene rings bonded to boron atoms (number in one molecule) may be 1 to 4, 1 to 3, 2 to 4, 2 to 3, or 3 to 4, or may be 3, from the viewpoint of making it easier to lower the reaction initiation temperature.
• Component (A) may have an unsubstituted naphthalene ring, or a naphthalene ring having a substituent.
• substituent include a halogen atom, an alkyl group, an aryl group, and an alkoxy group.
• Component (A) may have an alkyl group bonded to the boron atom, from the viewpoint of easily lowering the reaction initiation temperature.
• the number of alkyl groups bonded to the boron atom (the number in one molecule) may be 1 to 3, or 1 to 2, from the viewpoint of easily lowering the reaction initiation temperature.
• the number of carbon atoms in the alkyl group bonded to the boron atom may be within the following ranges from the viewpoint of easily lowering the reaction initiation temperature.
• the number of carbon atoms in the alkyl group may be 1 or more, 2 or more, 3 or more, or 4 or more.
• the number of carbon atoms in the alkyl group may be 12 or less, 10 or less, 8 or less, 6 or less, 5 or less, or 4 or less. From these viewpoints, the number of carbon atoms in the alkyl group may be 1-12, 1-8, 1-4, 2-12, 2-8, 2-4, 3-12, 3-8, 3-4, 4-12, or 4-8.
• Component (A) may have a functional group other than a naphthalene ring (naphthyl group) and an alkyl group as the functional group bonded to the boron atom.
• functional groups include aryl groups other than naphthyl groups (e.g., phenyl groups).
• Examples of the counter cation in component (a1) include quaternary ammonium ion, tertiary ammonium ion, secondary ammonium ion, primary ammonium ion, ammonium ion, imidazolium ion, imidazolinium ion, pyridinium ion, alkali metal ion (sodium ion, potassium ion, etc.), phosphonium cation, sulfonium cation, iodonium cation, etc.
• Component (a1) may or may not contain a metal ion.
• Component (a1) may contain a quaternary ammonium ion as a counter cation from the viewpoint of making it easier to lower the reaction initiation temperature.
• component (a1) may contain a quaternary ammonium ion having an alkyl group bonded to the nitrogen atom as a counter cation, and may contain a quaternary ammonium ion having at least one type selected from the group consisting of a straight-chain alkyl group bonded to the nitrogen atom and a branched alkyl group bonded to the nitrogen atom.
• the number of carbon atoms in the alkyl group bonded to the nitrogen atom may be within the following ranges from the viewpoint of easily lowering the reaction initiation temperature.
• the number of carbon atoms in the alkyl group may be 1 or more, 2 or more, 3 or more, or 4 or more.
• the number of carbon atoms in the alkyl group may be 18 or less, 16 or less, 14 or less, 12 or less, 10 or less, 8 or less, 6 or less, 5 or less, or 4 or less. From these viewpoints, the number of carbon atoms in the alkyl group may be 1 to 18, 1 to 8, 1 to 4, 2 to 6, 4 to 18, or 4 to 8.
• quaternary ammonium ions include tetraalkylammonium ions, trialkylammonium ions, dialkylammonium ions, monoalkylammonium ions, tetraarylammonium ions, triarylammonium ions, diarylammonium ions, and monoarylammonium ions.
• Component (a1) may contain a tetraalkylammonium ion as a counter cation, from the viewpoint of making it easier to lower the reaction initiation temperature.
• tetraalkylammonium ions include tetramethylammonium ion, tetraethylammonium ion, tetrapropylammonium ion, tetrabutylammonium ion (e.g., tetra-n-butylammonium ion), tetrahexylammonium ion, triethylmethylammonium ion, tributylethylammonium ion, trimethyldecylammonium ion, etc.
• Component (a1) may contain tetrabutylammonium ion as a counter cation, from the viewpoint of making it easier to lower the reaction initiation temperature.
• the content of the (a1) component may be in the following range based on the total mass of the polymerizable composition.
• the content of the (a1) component may be 0.01 mass% or more, 0.05 mass% or more, 0.10 mass% or more, 0.20 mass% or more, 0.30 mass% or more, 0.40 mass% or more, 0.50 mass% or more, 0.60 mass% or more, 0.70 mass% or more, 0.80 mass% or more, 0.90 mass% or more, 1.00 mass% or more, 1.10 mass% or more, 1.15 mass% or more, or 1.20 mass% or more.
• the content of the (a1) component may be 20.00% by mass or less, 15.00% by mass or less, 10.00% by mass or less, 8.00% by mass or less, 7.00% by mass or less, 6.00% by mass or less, 5.00% by mass or less, 4.00% by mass or less, 3.00% by mass or less, 2.00% by mass or less, 1.50% by mass or less, 1.20% by mass or less, 1.10% by mass or less, 1.00% by mass or less, 0.90% by mass or less, 0.80% by mass or less, 0.70% by mass or less, 0.60% by mass or less, 0.50% by mass or less, or 0.40% by mass or less.
• the content of the (a1) component may be 0.01 to 20.00 mass%, 0.30 to 20.00 mass%, 0.70 to 20.00 mass%, 0.01 to 2.00 mass%, 0.30 to 2.00 mass%, 0.70 to 2.00 mass%, 0.01 to 1.00 mass%, 0.30 to 1.00 mass%, or 0.70 to 1.00 mass%.
• the adhesive strength can also be adjusted by adjusting the content of the (a1) component.
• the polymerizable composition according to this embodiment contains, as component (B), at least one selected from the group consisting of aromatic carboxylic acid b, a salt of aromatic carboxylic acid b, and a hydrate of aromatic carboxylic acid b (excluding compounds corresponding to component (a1)).
• component (B) at least one selected from the group consisting of aromatic carboxylic acid b, a salt of aromatic carboxylic acid b, and a hydrate of aromatic carboxylic acid b (excluding compounds corresponding to component (a1)).
• salts of aromatic carboxylic acid b include alkali metal salts such as sodium salts and potassium salts.
• At least one selected from the group consisting of aromatic carboxylic acid b, a salt of aromatic carboxylic acid b, and a hydrate of aromatic carboxylic acid b may be at least one selected from the group consisting of aromatic carboxylic acid b and a hydrate of aromatic carboxylic acid b, or may be aromatic carboxylic acid b.
• the aromatic carboxylic acid b has at least one aromatic ring.
• the number of aromatic rings (the number in one molecule) may be 1, from the viewpoint of easily lowering the reaction initiation temperature.
• aromatic rings include a benzene ring and a naphthalene ring.
• the aromatic carboxylic acid b may include an aromatic carboxylic acid having a benzene ring, from the viewpoint of easily lowering the reaction initiation temperature.
• the aromatic carboxylic acid b has a carboxy group bonded to the aromatic ring.
• the aromatic carboxylic acid b may include an aromatic carboxylic acid having a hydroxy group (phenolic hydroxy group) bonded to the aromatic ring, from the viewpoint of easily lowering the reaction initiation temperature and easily obtaining excellent storage stability (excellent storage stability with respect to the reaction initiation temperature; the same applies below).
• the aromatic carboxylic acid b may have a hydroxy group bonded to the para position relative to the carboxy group bonded to the aromatic ring, may have one or two hydroxy groups bonded to the ortho position relative to the carboxy group bonded to the aromatic ring, or may have one or two hydroxy groups bonded to the meta position relative to the carboxy group bonded to the aromatic ring, from the viewpoint of easily lowering the reaction initiation temperature, easily obtaining excellent storage stability, and easily obtaining excellent adhesive strength.
• the number of carboxy groups bonded to the aromatic ring (the number in one molecule) may be 1, from the viewpoint of easily lowering the reaction initiation temperature and easily obtaining excellent storage stability.
• the number of hydroxy groups (the number in one molecule) or the number of hydroxy groups bonded to the aromatic ring (the number in one molecule) may be 1 to 4, 1 to 3, 1 to 2, 2 to 4, 2 to 3, or 3 to 4, or may be 2, or may be 3, from the viewpoint of easily lowering the reaction initiation temperature and easily obtaining excellent storage stability.
• the aromatic ring of the aromatic carboxylic acid b may have a substituent other than a carboxy group and a hydroxy group, or may not have a substituent other than a carboxy group and a hydroxy group.
• substituents include an alkyl group, an alkoxy group, etc.
• aromatic carboxylic acids b include dihydroxybenzoic acids such as 3,4-dihydroxybenzoic acid (protocatechuic acid), 3,5-dihydroxybenzoic acid ( ⁇ -resorcylic acid), 2,3-dihydroxybenzoic acid (2-pyrocatechuic acid), 2,4-dihydroxybenzoic acid ( ⁇ -resorcylic acid), 2,4-dihydroxy-6-methylbenzoic acid (orsellinic acid), 2,5-dihydroxybenzoic acid (gentisic acid), and 2,6-dihydroxybenzoic acid ( ⁇ -resorcylic acid); and trihydroxybenzoic acids such as 3,4,5-trihydroxybenzoic acid (gallic acid) and 2,4,6-trihydroxybenzoic acid (phloroglucinol carboxylic acid).
• dihydroxybenzoic acids such as 3,4-dihydroxybenzoic acid (protocatechuic acid), 3,5-dihydroxybenzoic acid ( ⁇ -resorcylic acid), 2,3-dihydroxybenz
• the aromatic carboxylic acid b may include at least one selected from the group consisting of 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, and 3,4,5-trihydroxybenzoic acid, and may include at least one selected from the group consisting of 3,4-dihydroxybenzoic acid and 3,4,5-trihydroxybenzoic acid.
• the aromatic carboxylic acid b may contain at least one selected from the group consisting of 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, and 3,4,5-trihydroxybenzoic acid, may contain at least one selected from the group consisting of 3,4-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, and 3,4,5-trihydroxybenzoic acid, and may contain 3,4-dihydroxybenzoic acid. From the viewpoint of easily lowering the reaction initiation temperature, the aromatic carboxylic acid b may contain 3,4,5-trihydroxybenzoic acid.
• the aromatic carboxylic acid b may contain at least one selected from the group consisting of 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, and 3,4,5-trihydroxybenzoic acid.
• the content of component (B) may be 50.00 mass% or more, more than 50.00 mass%, 70.00 mass% or more, 80.00 mass% or more, 90.00 mass% or more, 92.00 mass% or more, 95.00 mass% or more, 97.00 mass% or more, 98.00 mass% or more, 99.00 mass% or more, or substantially 100.00 mass% based on the total amount of aromatic carboxylic acid, aromatic carboxylic acid salt, and aromatic carboxylic acid hydrate contained in the polymerizable composition, from the viewpoint of easily lowering the reaction initiation temperature.
• the content of the (B) component may be in the following range based on the total mass of the polymerizable composition. From the viewpoint of easily lowering the reaction initiation temperature, the content of the (B) component may be 0.01 mass% or more, 0.05 mass% or more, 0.10 mass% or more, 0.30 mass% or more, 0.50 mass% or more, 0.80 mass% or more, 1.00 mass% or more, 1.20 mass% or more, 1.30 mass% or more, 1.40 mass% or more, 1.50 mass% or more, 1.60 mass% or more, 1.80 mass% or more, 1.90 mass% or more, 2.00 mass% or more, 2.50 mass% or more, 3.00 mass% or more, or 3.50 mass% or more.
• the content of the (B) component may be 10.00% by mass or less, 8.00% by mass or less, 6.00% by mass or less, 5.00% by mass or less, 4.00% by mass or less, 3.50% by mass or less, 3.00% by mass or less, 2.50% by mass or less, 2.00% by mass or less, 1.90% by mass or less, 1.80% by mass or less, 1.60% by mass or less, 1.50% by mass or less, 1.40% by mass or less, or 1.30% by mass or less.
• the content of the (B) component may be 0.01 to 10.00 mass%, 0.01 to 2.50 mass%, 0.01 to 2.00 mass%, 1.00 to 10.00 mass%, 1.00 to 2.50 mass%, 1.00 to 2.00 mass%, 1.50 to 10.00 mass%, 1.50 to 2.50 mass%, or 1.50 to 2.00 mass%.
• the adhesive strength can also be adjusted by adjusting the content of the (B) component.
• the mass ratio R1 of the content of the (B) component to the content of the (a1) component ((B) component/(a1) component) may be in the following range from the viewpoint of easily lowering the reaction initiation temperature.
• the mass ratio R1 may be 0.01 or more, 0.05 or more, 0.10 or more, 0.30 or more, 0.50 or more, 0.80 or more, 1.00 or more, 1.20 or more, 1.50 or more, 1.80 or more, 2.00 or more, 2.50 or more, 3.00 or more, 3.50 or more, 4.00 or more, or 4.50 or more.
• the mass ratio R1 may be 10.00 or less, 8.00 or less, 6.00 or less, 5.00 or less, 4.50 or less, 4.00 or less, 3.50 or less, 3.00 or less, 2.50 or less, 2.00 or less, 1.80 or less, 1.50 or less, or 1.20 or less. From these viewpoints, the mass ratio R1 may be 0.01 to 10.00, 0.01 to 6.00, 0.01 to 3.00, 1.00 to 10.00, 1.00 to 6.00, 1.00 to 3.00, 1.50 to 10.00, 1.50 to 6.00, or 1.50 to 3.00.
• component (C) it is easy to improve the adhesion between the polymerizable composition or its cured product and a substrate (substrate containing a metal material (e.g. aluminum), glass, etc.).
• c11 represents an integer of 1 to 3
• c12 represents an integer of 0 to 2
• c11 + c12 is 3
• R c1 represents a monovalent group.
• c11 may be 1 to 2, or 2 to 3, from the viewpoint of making it easier to lower the reaction initiation temperature and to obtain excellent adhesive strength.
• the component (C) may have a monovalent group (R c1 in general formula ( c1 )) other than a hydroxy group as a functional group bonded to the phosphorus atom.
• the monovalent group include a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group (e.g., a phenyl group), and a (meth)acryloyl group-containing group.
• the (meth)acryloyl group-containing group is a group having at least one group selected from the group consisting of an acryloyl group and a methacryloyl group.
• c21 represents an integer of 1 or 2
• c22 represents an integer of 1 or 2
• c21 + c22 is 3
• c23 and c24 each independently represent an integer of 1 or more
• R c2 represents a hydrogen atom or a methyl group.
• c23 may be 1 to 8, 1 to 6, 1 to 5, 3 to 8, 3 to 6, 3 to 5, 5 to 8, or 5 to 6, from the viewpoint of easily lowering the reaction initiation temperature and easily obtaining excellent adhesive strength.
• c24 may be 1 to 4, 2 to 4, 1 to 3, or 1 to 2, from the viewpoint of easily lowering the reaction initiation temperature and easily obtaining excellent adhesive strength.
• the content of component (C) may be 50.00 mass% or more, more than 50.00 mass%, 70.00 mass% or more, 80.00 mass% or more, 90.00 mass% or more, 92.00 mass% or more, 95.00 mass% or more, 97.00 mass% or more, 98.00 mass% or more, 99.00 mass% or more, or substantially 100.00 mass% based on the total mass of the phosphorus-containing compound (compound containing a phosphorus atom) contained in the polymerizable composition, from the viewpoint of easily lowering the reaction initiation temperature and easily obtaining excellent adhesive strength.
• the content of the (C) component may be in the following range based on the total mass of the polymerizable composition.
• the content of the (C) component may be 0.01 mass% or more, 0.05 mass% or more, 0.10 mass% or more, 0.20 mass% or more, 0.30 mass% or more, 0.40 mass% or more, 0.50 mass% or more, 0.60 mass% or more, 0.70 mass% or more, 0.80 mass% or more, 0.90 mass% or more, 1.00 mass% or more, 1.20 mass% or more, 1.50 mass% or more, or 1.80 mass% or more.
• the content of component (C) may be 10.00 mass% or less, 8.00 mass% or less, 6.00 mass% or less, 5.00 mass% or less, 4.00 mass% or less, 3.00 mass% or less, 2.00 mass% or less, 1.80 mass% or less, 1.50 mass% or less, 1.20 mass% or less, 1.00 mass% or less, 0.90 mass% or less, 0.80 mass% or less, 0.70 mass% or less, 0.60 mass% or less, 0.50 mass% or less, or 0.40 mass% or less.
• component (C) may be 0.01 to 10.00% by mass, 0.01 to 2.00% by mass, 0.01 to 1.00% by mass, 0.20 to 10.00% by mass, 0.20 to 2.00% by mass, 0.20 to 1.00% by mass, 0.50 to 10.00% by mass, 0.50 to 2.00% by mass, or 0.50 to 1.00% by mass.
• the mass ratio R21 of the content of the (C) component to the content of the (a1) component ((C) component/(a1) component) may be in the following range from the viewpoint of easily lowering the reaction initiation temperature and easily obtaining excellent storage stability.
• the mass ratio R21 may be 0.01 or more, 0.05 or more, 0.08 or more, 0.10 or more, 0.20 or more, 0.30 or more, 0.40 or more, 0.45 or more, 0.50 or more, 0.60 or more, 0.80 or more, 1.00 or more, 1.20 or more, 1.30 or more, 1.50 or more, 1.80 or more, 2.00 or more, or 2.30 or more.
• the mass ratio R21 may be 10.00 or less, 8.00 or less, 6.00 or less, 5.00 or less, 4.00 or less, 3.00 or less, 2.30 or less, 2.00 or less, 1.80 or less, 1.50 or less, 1.30 or less, 1.20 or less, 1.00 or less, 0.80 or less, 0.60 or less, 0.50 or less, 0.45 or less, or 0.40 or less. From these viewpoints, the mass ratio R21 may be 0.01 to 10.00, 0.01 to 5.00, 0.01 to 2.00, 0.50 to 10.00, 0.50 to 5.00, 0.50 to 2.00, 1.00 to 10.00, 1.00 to 5.00, or 1.00 to 2.00.
• the mass ratio R22 of the content of the (C) component to the content of the (B) component may be in the following range from the viewpoint of easily lowering the reaction initiation temperature and easily obtaining excellent adhesive strength.
• the mass ratio R22 may be 0.01 or more, 0.05 or more, 0.10 or more, 0.15 or more, 0.20 or more, 0.25 or more, 0.30 or more, 0.35 or more, 0.40 or more, 0.45 or more, 0.50 or more, 0.55 or more, 0.60 or more, 0.65 or more, 0.70 or more, 0.75 or more, 0.80 or more, 0.85 or more, 0.90 or more, or 1.00 or more.
• the mass ratio R22 may be 5.00 or less, 4.00 or less, 3.00 or less, 2.00 or less, 1.50 or less, 1.00 or less, 0.90 or less, 0.85 or less, 0.80 or less, 0.75 or less, 0.70 or less, 0.65 or less, 0.60 or less, 0.55 or less, 0.50 or less, 0.45 or less, 0.40 or less, 0.35 or less, 0.30 or less, 0.25 or less, 0.20 or less, or 0.15 or less. From these perspectives, the mass ratio R22 may be 0.01 to 5.00, 0.01 to 1.50, 0.01 to 0.80, 0.20 to 5.00, 0.20 to 1.50, 0.20 to 0.80, 0.40 to 5.00, 0.40 to 1.50, or 0.40 to 0.80.
• the polymerizable composition according to this embodiment may contain a polymerizable compound (excluding compounds corresponding to the components (a1), (B) or (C)) as the component (D).
• component (D) examples include radically polymerizable compounds, cationic polymerizable compounds, and anionic polymerizable compounds.
• Component (D) may contain a radically polymerizable compound from the viewpoint of making it easier to lower the reaction initiation temperature.
• the (D) component may include (meth)acrylate compounds, maleimide compounds, vinyl ether compounds, allyl compounds, styrene compounds, (meth)acrylamide compounds, nadimide compounds, natural rubber, isoprene rubber, butyl rubber, nitrile rubber, butadiene rubber, styrene-butadiene rubber, acrylonitrile-butadiene rubber, carboxylated nitrile rubber, epoxy compounds, oxetane compounds, lactone compounds, etc.
• compounds that fall under both (meth)acrylate compounds and other compounds are classified as (meth)acrylate compounds.
• the (D) component may contain a compound having an ethylenically unsaturated bond and may contain a (meth)acrylate compound. From the viewpoint of easily lowering the reaction initiation temperature, the (D) component may contain a compound different from an epoxy compound and may contain a compound without an epoxy group.
• (Meth)acrylate compounds include (poly)urethane (meth)acrylate, epoxy (meth)acrylate, methyl (meth)acrylate, polyether (meth)acrylate, polyester (meth)acrylate, polybutadiene (meth)acrylate, silicone (meth)acrylate, ethyl (meth)acrylate, 2-cyanoethyl (meth)acrylate, 2-(2-ethoxyethoxy)ethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-hexyl (meth)acrylate, Acrylate, 2-hydroxyethyl (meth)acrylate, isopropyl (meth)acrylate, hydroxypropyl (meth)acrylate, isobutyl (meth)acrylate, isobornyl (meth)acrylate, isodecyl (meth)acrylate, isooctyl (
• Polyurethane(meth)acrylate and “urethane(meth)acrylate” are collectively referred to as “(poly)urethane(meth)acrylate”.
• the (D) component may contain a bifunctional (meth)acrylate compound.
• the (D) component may contain a urethane (meth)acrylate compound having a polycarbonate skeleton (hereinafter referred to as "component (d1)”), may contain a urethane (meth)acrylate compound having a structure derived from a polycarbonate polyol, or may contain a compound represented by the following general formula (d1), from the viewpoint of making it easier to lower the reaction initiation temperature.
• component (d1) a urethane (meth)acrylate compound having a polycarbonate skeleton
• R1 represents a hydrogen atom or a methyl group
• j represents an integer of 1 to 3
• k represents an integer of 2 to 7
• m represents an integer of 1 to 8
• n represents an integer of 5 to 7.
• j may be 1 to 2 or 2 to 3
• k may be 2 to 3 or 3 to 5
• m may be 1 to 6, 1 to 4 or 1 to 2
• n may be 5 to 6 or 6 to 7.
• the weight average molecular weight of the (d1) component may be 1000 or more, 3000 or more, 5000 or more, 8000 or more, 10000 or more, 12000 or more, 13000 or more, 14000 or more, or 15000 or more, from the viewpoint of easily lowering the reaction initiation temperature.
• the weight average molecular weight of the (d1) component may be 100000 or less, 50000 or less, 30000 or less, 25000 or less, 20000 or less, 18000 or less, or 15000 or less, from the viewpoint of easily lowering the reaction initiation temperature. From these viewpoints, the weight average molecular weight of the (d1) component may be 1000 to 100000, 5000 to 50000, or 10000 to 30000.
• the content of the (d1) component may be in the following range based on the total mass of the (D) component.
• the content of the (d1) component may be 10.00 mass% or more, 15.00 mass% or more, 20.00 mass% or more, 25.00 mass% or more, 30.00 mass% or more, 35.00 mass% or more, 40.00 mass% or more, 45.00 mass% or more, 50.00 mass% or more, or 55.00 mass% or more.
• the content of the (d1) component may be 90.00 mass% or less, 85.00 mass% or less, 80.00 mass% or less, 75.00 mass% or less, 70.00 mass% or less, 65.00 mass% or less, or 60.00 mass% or less.
• the content of the (d1) component may be 10.00 to 90.00 mass%, 10.00 to 80.00 mass%, 10.00 to 70.00 mass%, 20.00 to 90.00 mass%, 20.00 to 80.00 mass%, 20.00 to 70.00 mass%, 40.00 to 90.00 mass%, 40.00 to 80.00 mass%, or 40.00 to 70.00 mass%.
• the content of the (d1) component may be in the following ranges based on the total mass of the polymerizable composition.
• the content of the (d1) component may be 5.00 mass% or more, 10.00 mass% or more, 15.00 mass% or more, or 20.00 mass% or more.
• the content of the (d1) component may be 50.00 mass% or less, 45.00 mass% or less, 40.00 mass% or less, 35.00 mass% or less, 30.00 mass% or less, or 25.00 mass% or less.
• the content of the (d1) component may be 5.00 to 50.00 mass%, 5.00 to 40.00 mass%, 5.00 to 30.00 mass%, 10.00 to 50.00 mass%, 10.00 to 40.00 mass%, 10.00 to 30.00 mass%, 20.00 to 50.00 mass%, 20.00 to 40.00 mass%, or 20.00 to 30.00 mass%.
• the (D) component may contain isocyanuric acid alkylene oxide modified di(meth)acrylate (excluding compounds corresponding to the (d1) component; hereinafter referred to as "(d2) component”), or may contain isocyanuric acid ethylene oxide modified di(meth)acrylate, in order to facilitate lowering the reaction initiation temperature.
• the content of the (d2) component may be in the following ranges based on the total mass of the (D) component.
• the content of the (d2) component may be 1.00 mass% or more, 5.00 mass% or more, 10.00 mass% or more, 15.00 mass% or more, or 20.00 mass% or more.
• the content of the (d2) component may be 50.00 mass% or less, 45.00 mass% or less, 40.00 mass% or less, 35.00 mass% or less, 30.00 mass% or less, or 25.00 mass% or less.
• the content of the (d2) component may be 1.00 to 50.00 mass%, 1.00 to 40.00 mass%, 1.00 to 30.00 mass%, 10.00 to 50.00 mass%, 10.00 to 40.00 mass%, 10.00 to 30.00 mass%, 20.00 to 50.00 mass%, 20.00 to 40.00 mass%, or 20.00 to 30.00 mass%.
• the content of the (d2) component may be in the following ranges based on the total mass of the polymerizable composition.
• the content of the (d2) component may be 1.00 mass% or more, 3.00 mass% or more, 5.00 mass% or more, 8.00 mass% or more, or 9.00 mass% or more.
• the content of the (d2) component may be 30.00 mass% or less, 25.00 mass% or less, 20.00 mass% or less, 15.00 mass% or less, or 10.00 mass% or less.
• the content of the (d2) component may be 1.00 to 30.00 mass%, 1.00 to 20.00 mass%, 1.00 to 10.00 mass%, 5.00 to 30.00 mass%, 5.00 to 20.00 mass%, 5.00 to 10.00 mass%, 7.00 to 30.00 mass%, 7.00 to 20.00 mass%, or 7.00 to 10.00 mass%.
• the (D) component may contain a di(meth)acrylate compound having at least one selected from the group consisting of a dicyclopentanyl structure and a dicyclopentenyl structure (excluding compounds corresponding to the (d1) component or the (d2) component; hereinafter referred to as "(d3) component"), from the viewpoint of easily lowering the reaction initiation temperature, and may contain at least one selected from the group consisting of dimethylol tricyclodecane di(meth)acrylate and tricyclodecane diol di(meth)acrylate.
• the content of the (d3) component may be in the following ranges based on the total mass of the (D) component.
• the content of the (d3) component may be 1.00 mass% or more, 5.00 mass% or more, 10.00 mass% or more, 15.00 mass% or more, or 20.00 mass% or more.
• the content of the (d3) component may be 50.00 mass% or less, 45.00 mass% or less, 40.00 mass% or less, 35.00 mass% or less, 30.00 mass% or less, or 25.00 mass% or less.
• the content of the (d3) component may be 1.00 to 50.00 mass%, 1.00 to 40.00 mass%, 1.00 to 30.00 mass%, 10.00 to 50.00 mass%, 10.00 to 40.00 mass%, 10.00 to 30.00 mass%, 20.00 to 50.00 mass%, 20.00 to 40.00 mass%, or 20.00 to 30.00 mass%.
• the content of the (d3) component may be in the following ranges based on the total mass of the polymerizable composition.
• the content of the (d3) component may be 1.00 mass% or more, 3.00 mass% or more, 5.00 mass% or more, 8.00 mass% or more, or 9.00 mass% or more.
• the content of the (d3) component may be 30.00 mass% or less, 25.00 mass% or less, 20.00 mass% or less, 15.00 mass% or less, or 10.00 mass% or less.
• the content of the (d3) component may be 1.00 to 30.00 mass%, 1.00 to 20.00 mass%, 1.00 to 10.00 mass%, 5.00 to 30.00 mass%, 5.00 to 20.00 mass%, 5.00 to 10.00 mass%, 7.00 to 30.00 mass%, 7.00 to 20.00 mass%, or 7.00 to 10.00 mass%.
• the content of the (D) component may be in the following range based on the total mass of the polymerizable composition.
• the content of the (D) component may be 10.00 mass% or more, 15.00 mass% or more, 20.00 mass% or more, 25.00 mass% or more, 30.00 mass% or more, 35.00 mass% or more, or 40.00 mass% or more.
• the content of the (D) component may be 80.00 mass% or less, 75.00 mass% or less, 70.00 mass% or less, 65.00 mass% or less, 60.00 mass% or less, 55.00 mass% or less, 50.00 mass% or less, or 45.00 mass% or less.
• component (D) may be 10.00 to 80.00 mass%, 10.00 to 60.00 mass%, 10.00 to 50.00 mass%, 30.00 to 80.00 mass%, 30.00 to 60.00 mass%, 30.00 to 50.00 mass%, 35.00 to 80.00 mass%, 35.00 to 60.00 mass%, or 35.00 to 50.00 mass%.
• the mass ratio R31 of the content of the (D) component to the content of the (a1) component ((D) component/(a1) component) may be in the following range from the viewpoint of easily lowering the reaction initiation temperature.
• the mass ratio R31 may be 1.00 or more, 5.00 or more, 10.00 or more, 20.00 or more, 30.00 or more, 40.00 or more, 50.00 or more, 60.00 or more, 80.00 or more, or 100.00 or more.
• the mass ratio R31 may be 300.00 or less, 250.00 or less, 200.00 or less, 150.00 or less, 120.00 or less, 100.00 or less, 80.00 or less, 60.00 or less, 50.00 or less, or 40.00 or less.
• the mass ratio R31 may be 1.00 to 300.00, 1.00 to 120.00, 1.00 to 60.00, 20.00 to 300.00, 20.00 to 120.00, 20.00 to 60.00, 30.00 to 300.00, 30.00 to 120.00, or 30.00 to 60.00.
• the mass ratio R32 of the content of the (D) component to the content of the (B) component may be in the following range. From the viewpoint of easily obtaining excellent storage stability, the mass ratio R32 may be 1.00 or more, 5.00 or more, 10.00 or more, 15.00 or more, 20.00 or more, 25.00 or more, or 30.00 or more. From the viewpoint of easily lowering the reaction initiation temperature, the mass ratio R32 may be 300.00 or less, 200.00 or less, 100.00 or less, 80.00 or less, 50.00 or less, 45.00 or less, 40.00 or less, 35.00 or less, 30.00 or less, 25.00 or less, 20.00 or less, or 15.00 or less.
• the mass ratio R32 may be 1.00 to 300.00, 1.00 to 50.00, 1.00 to 30.00, 10.00 to 300.00, 10.00 to 50.00, 10.00 to 30.00, 20.00 to 300.00, 20.00 to 50.00, or 20.00 to 30.00.
• the mass ratio R33 of the content of the (D) component to the content of the (C) component may be in the following range from the viewpoint of easily lowering the reaction initiation temperature.
• the mass ratio R33 may be 1.00 or more, 5.00 or more, 10.00 or more, 15.00 or more, 20.00 or more, 25.00 or more, 30.00 or more, 35.00 or more, 40.00 or more, 45.00 or more, 50.00 or more, 60.00 or more, 70.00 or more, 80.00 or more, 90.00 or more, or 100.00 or more.
• the mass ratio R33 may be 300.00 or less, 250.00 or less, 200.00 or less, 150.00 or less, 140.00 or less, 100.00 or less, 90.00 or less, 80.00 or less, 70.00 or less, 60.00 or less, 50.00 or less, 45.00 or less, 40.00 or less, 35.00 or less, 30.00 or less, or 25.00 or less. From these perspectives, the mass ratio R33 may be 1.00 to 300.00, 1.00 to 100.00, 1.00 to 60.00, 20.00 to 300.00, 20.00 to 100.00, 20.00 to 60.00, 30.00 to 300.00, 30.00 to 100.00, or 30.00 to 60.00.
• the polymerizable composition according to this embodiment may contain a polymerization initiator (excluding compounds corresponding to the components (a1), (B), (C) or (D)) as the component (E).
• the component (E) may contain a thermal polymerization initiator.
• examples of the component (E) include a radical polymerization initiator, a cationic polymerization initiator and an anionic polymerization initiator.
• the component (E) may contain a radical polymerization initiator from the viewpoint of making it easier to lower the reaction initiation temperature.
• Component (E) includes ketone peroxides such as methyl ethyl ketone peroxide, cyclohexanone peroxide, and methylcyclohexanone peroxide; peroxyketals such as 1,1-bis(tert-butylperoxy)cyclohexane, 1,1-bis(tert-butylperoxy)-2-methylcyclohexane, 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(tert-hexylperoxy)cyclohexane, and 1,1-bis(tert-hexylperoxy)-3,3,5-trimethylcyclohexane; hydroperoxides such as p-menthane hydroperoxide; ⁇ , ⁇ '-bis(tert-butylperoxy)diisopropylbenzene, dicumyl peroxide, tert-butylcumyl peroxide, and di
• the (E) component may contain a peroxide, an organic peroxide, at least one selected from the group consisting of peroxyketals and diacyl peroxides, a peroxyketal, 1,1-bis(tert-butylperoxy)cyclohexane, a diacyl peroxide, or a dilauroyl peroxide, from the viewpoints of easily lowering the reaction initiation temperature, easily obtaining excellent storage stability, and easily obtaining excellent adhesive strength.
• the content of the (E) component may be in the following range based on the total mass of the polymerizable composition. From the viewpoint of easily lowering the reaction initiation temperature, the content of the (E) component may be 0.10 mass% or more, 0.50 mass% or more, 1.00 mass% or more, 1.50 mass% or more, 2.00 mass% or more, 2.50 mass% or more, 3.00 mass% or more, 3.50 mass% or more, 4.00 mass% or more, or 4.50 mass% or more.
• the content of the (E) component may be 20.00 mass% or less, 15.00 mass% or less, 10.00 mass% or less, 9.00 mass% or less, 8.00 mass% or less, 7.00 mass% or less, 6.00 mass% or less, or 5.00 mass% or less.
• component (E) may be 0.10 to 20.00% by mass, 0.10 to 10.00% by mass, 0.10 to 5.00% by mass, 1.00 to 20.00% by mass, 1.00 to 10.00% by mass, 1.00 to 5.00% by mass, 3.00 to 20.00% by mass, 3.00 to 10.00% by mass, or 3.00 to 5.00% by mass.
• the mass ratio R41 of the content of the (E) component to the content of the (a1) component ((E) component/(a1) component) may be in the following range from the viewpoint of easily lowering the reaction initiation temperature.
• the mass ratio R41 may be 0.10 or more, 0.50 or more, 1.00 or more, 2.00 or more, 3.00 or more, 4.00 or more, 5.00 or more, 6.00 or more, 8.00 or more, or 10.00 or more.
• the mass ratio R41 may be 50.00 or less, 30.00 or less, 20.00 or less, 15.00 or less, 10.00 or less, 8.00 or less, 6.00 or less, 5.00 or less, or 4.00 or less.
• the mass ratio R41 may be 0.10 to 50.00, 0.10 to 15.00, 0.10 to 6.00, 3.00 to 50.00, 3.00 to 15.00, 3.00 to 6.00, 5.00 to 50.00, 5.00 to 15.00, or 5.00 to 6.00.
• the mass ratio R42 of the content of the (E) component to the content of the (B) component may be in the following range. From the viewpoint of easily obtaining excellent storage stability, the mass ratio R42 may be 0.10 or more, 0.50 or more, 1.00 or more, 1.50 or more, 2.00 or more, 2.50 or more, 3.00 or more, or 3.50 or more. From the viewpoint of easily lowering the reaction initiation temperature, the mass ratio R42 may be 50.00 or less, 30.00 or less, 20.00 or less, 15.00 or less, 10.00 or less, 8.00 or less, 5.00 or less, 4.00 or less, 3.50 or less, 3.00 or less, 2.50 or less, 2.00 or less, or 1.50 or less.
• the mass ratio R42 may be 0.10 to 50.00, 0.10 to 20.00, 0.10 to 3.00, 1.00 to 50.00, 1.00 to 20.00, 1.00 to 3.00, 2.00 to 50.00, 2.00 to 20.00, or 2.00 to 3.00.
• the mass ratio R43 of the content of the (E) component to the content of the (C) component may be in the following range from the viewpoint of easily lowering the reaction initiation temperature and easily obtaining excellent storage stability.
• the mass ratio R43 may be 0.10 or more, 0.50 or more, 1.00 or more, 1.50 or more, 2.00 or more, 2.50 or more, 3.00 or more, 3.50 or more, 4.00 or more, 4.50 or more, 5.00 or more, 5.50 or more, 6.00 or more, 6.50 or more, 7.00 or more, 8.00 or more, 9.00 or more, 10.00 or more, or 12.00 or more.
• the mass ratio R43 may be 50.00 or less, 30.00 or less, 20.00 or less, 15.00 or less, 12.00 or less, 10.00 or less, 9.00 or less, 8.00 or less, 7.00 or less, 6.50 or less, 6.00 or less, 5.50 or less, 5.00 or less, 4.50 or less, 4.00 or less, 3.50 or less, 3.00 or less, or 2.50 or less. From these viewpoints, the mass ratio R43 may be 0.10 to 50.00, 0.10 to 10.00, 0.10 to 6.00, 1.00 to 50.00, 1.00 to 10.00, 1.00 to 6.00, 3.00 to 50.00, 3.00 to 10.00, or 3.00 to 6.00.
• the mass ratio R44 of the content of the (E) component to the content of the (D) component may be in the following range from the viewpoint of easily lowering the reaction initiation temperature.
• the mass ratio R44 may be 0.01 or more, 0.03 or more, 0.05 or more, 0.08 or more, or 0.10 or more.
• the mass ratio R44 may be 5.00 or less, 3.00 or less, 1.00 or less, 0.50 or less, 0.30 or less, 0.20 or less, or 0.15 or less.
• the mass ratio R44 may be 0.01 to 5.00, 0.01 to 1.00, 0.01 to 0.50, 0.05 to 5.00, 0.05 to 1.00, 0.05 to 0.50, 0.10 to 5.00, 0.10 to 1.00, or 0.10 to 0.50.
• the polymerizable composition according to this embodiment may contain a thermoplastic resin as component (F).
• the (F) component examples include phenoxy resin, polyester, polyurethane (excluding polyester urethane), polyester urethane, ethylene vinyl acetate copolymer, butyral resin, etc. From the viewpoint of making it easier to lower the reaction initiation temperature, the (F) component may contain at least one selected from the group consisting of polyester urethane and ethylene vinyl acetate copolymer.
• the content of the (F) component may be in the following range based on the total mass of the polymerizable composition.
• the content of the (F) component may be 10.00 mass% or more, 15.00 mass% or more, 20.00 mass% or more, 25.00 mass% or more, 30.00 mass% or more, 35.00 mass% or more, 40.00 mass% or more, 45.00 mass% or more, or 50.00 mass% or more.
• the content of the (F) component may be 90.00 mass% or less, 85.00 mass% or less, 80.00 mass% or less, 75.00 mass% or less, 70.00 mass% or less, 65.00 mass% or less, 60.00 mass% or less, or 55.00 mass% or less.
• component (F) may be 10.00 to 90.00 mass%, 10.00 to 70.00 mass%, 10.00 to 60.00 mass%, 30.00 to 90.00 mass%, 30.00 to 70.00 mass%, 30.00 to 60.00 mass%, 40.00 to 90.00 mass%, 40.00 to 70.00 mass%, or 40.00 to 60.00 mass%.
• the polymerizable composition according to the present embodiment may contain components other than the above-mentioned components.
• examples of such components include water, organic solvents, coupling agents, fillers, softeners, accelerators (e.g., polymerization accelerators), anti-degradants, colorants, flame retardants, thixotropic agents, and the like.
• the polymerizable composition according to the present embodiment may contain at least one of these components, or may not contain at least one of these components.
• the polymerizable composition according to the present embodiment may not contain a filler, and may not contain an inorganic filler.
• the content of the filler or the content of the inorganic filler may be 50% by mass or less, less than 50% by mass, 10% by mass or less, 1% by mass or less, 0.1% by mass or less, or 0.01% by mass or less, based on the total mass of the polymerizable composition, and may be substantially 0% by mass.
• the polymerizable composition according to this embodiment may be in the form of a film.
• the thickness of the film-like polymerizable composition or the thickness of the cured product according to this embodiment may be in the following ranges.
• the thickness may be 1 ⁇ m or more, 3 ⁇ m or more, 5 ⁇ m or more, 8 ⁇ m or more, 10 ⁇ m or more, 12 ⁇ m or more, 15 ⁇ m or more, 18 ⁇ m or more, or 20 ⁇ m or more.
• the thickness may be 500 ⁇ m or less, 300 ⁇ m or less, 200 ⁇ m or less, 100 ⁇ m or less, 80 ⁇ m or less, 50 ⁇ m or less, 30 ⁇ m or less, or 20 ⁇ m or less.
• the thickness may be 1 to 500 ⁇ m, 1 to 100 ⁇ m, 1 to 50 ⁇ m, 5 to 500 ⁇ m, 5 to 100 ⁇ m, 5 to 50 ⁇ m, 10 to 500 ⁇ m, 10 to 100 ⁇ m, or 10 to 50 ⁇ m.
• the precipitate was washed with water and then vacuum dried to obtain a polyester polyol. After the polyester polyol was thoroughly dried, it was dissolved in MEK (methyl ethyl ketone) and put into a four-neck flask equipped with a stirrer, a dropping funnel, a reflux condenser and a nitrogen gas inlet tube. Further, dibutyltin dilaurate (catalyst) was added in an amount of 0.05 parts by mass relative to 100 parts by mass of polyester polyol, and 4,4'-diphenylmethane diisocyanate was dissolved in MEK in an amount of 50 parts by mass relative to 100 parts by mass of polyester polyol and added using a dropping funnel. The mixture was then stirred at 80°C for 4 hours to obtain polyester urethane (EU1).
• MEK methyl ethyl ketone
• Polymerizable compositions were prepared by mixing a toluene solution (solid content: 20% by mass) of polymerization initiator A (dilauroyl peroxide, product name: Peroyl L, manufactured by NOF Corporation) or a solution of polymerization initiator B (a solution of 1,1-bis(tert-butylperoxy)cyclohexane, product name: Perhexa C, manufactured by NOF Corporation, solid content: 80% by mass) with a methyl ethyl ketone/toluene mixed solution (mass ratio: 1/1, solid content: 40% by mass) of polyester urethane (EU1), and a toluene solution (solid content: 30% by mass) of ethylene vinyl acetate copolymer (product name: EV40W, manufactured by DuPont Co., Ltd.).
• polymerization initiator A diilauroyl peroxide, product name: Peroyl L, manufactured by NOF Corporation
• polymerization initiator B a solution of 1,1
• the amount of urethane acrylate (UA1) used was 25.00 parts by mass
• the amount of isocyanuric acid ethylene oxide modified diacrylate used was 10.00 parts by mass
• the amount of dimethylol tricyclodecane diacrylate used was 10.00 parts by mass
• the amount of polymerization initiator used was 5.00 parts by mass
• the amount of polyester urethane (EU1) used solid content was 47.50 parts by mass
• the amount of ethylene vinyl acetate copolymer used was 10.00 parts by mass
• the amount of ethylene vinyl acetate copolymer used was 10.00 parts by mass.
• the dosage (solid content) was 7.50 parts by mass.
• 3,4-dihydroxybenzoic acid protocatechuic acid, manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.
• 2,3-dihydroxybenzoic acid (2-pyrocatechuic acid, manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.)
• 2,4-dihydroxybenzoic acid ⁇ -resorcylic acid, manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.
• 2,5-dihydroxybenzoic acid gentisic acid, manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.
• 3,5-dihydroxybenzoic acid ⁇ -resorcylic acid, manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.
• 3,4,5-trihydroxybenzoic acid gallic acid, monohydrate, manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.
• Example 1 A polymerizable composition was prepared in the same manner as in Example A1, except that no acid component or phosphorus compound was used.
• the curing heat generation behavior of the film-like polymerizable composition was measured by differential scanning calorimetry (hereinafter referred to as "DSC"), and the onset temperature of the heat generation peak was obtained as an index of the reaction initiation temperature of polymerization.
• the DSC measurement was performed under the following conditions to obtain the reaction initiation temperature T1.
• the laminate film just after preparation in the examples was placed in a nylon poly bag (manufactured by Fukusuke Kogyo Co., Ltd., product name "Nylon Poly S Type”), and then the bag was sealed using a vacuum degassing sealer to enclose the laminate film. Furthermore, the bag was placed in an aluminum light-shielding bag.
• the above-mentioned polymerizable composition was applied to a PET film (with peeling treatment, thickness: 50 ⁇ m) using a bar coater (manufactured by Yasui Seiki Co., Ltd., product name "KNIFE COATER SNC-300"), and then dried in an oven at 60 ° C. for 3 minutes to produce a laminated film A having a film-like polymerizable composition of 20 ⁇ m thickness arranged on the PET film.
• This laminated film A was cut into a width of 1 mm and a length of 5 cm to obtain a laminated film B, and then this laminated film B was placed on a polyimide film (thickness: 25 ⁇ m).
• the film-like polymerizable composition was brought into contact with a glass plate (thickness: 1.1 mm) to interpose the film-like polymerizable composition between the polyimide film and the glass plate.
• a test piece was obtained by heating and pressing at 90 ° C. and 3 MPa for 30 seconds using a thermocompression device (manufactured by Takahashi Koki Co., Ltd.).
• the adhesive strength was measured by the 90-degree peel method (peel speed: 50 mm/min, 10 mm width, 25°C) in accordance with JIS Z 0237.
• the adhesive strength was measured using a small tabletop tester "EZ-LX” manufactured by Shimadzu Corporation. The results are shown in Tables 1 and 2.

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• 2023
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