WO2022210595A1 - 重合性組成物、光硬化性接着剤、硬化物の製造方法及び硬化物 - Google Patents
重合性組成物、光硬化性接着剤、硬化物の製造方法及び硬化物 Download PDFInfo
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- WO2022210595A1 WO2022210595A1 PCT/JP2022/015169 JP2022015169W WO2022210595A1 WO 2022210595 A1 WO2022210595 A1 WO 2022210595A1 JP 2022015169 W JP2022015169 W JP 2022015169W WO 2022210595 A1 WO2022210595 A1 WO 2022210595A1
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- 238000007789 sealing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-O thiolan-1-ium Chemical class C1CC[SH+]C1 RAOIDOHSFRTOEL-UHFFFAOYSA-O 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/223—Di-epoxy compounds together with monoepoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/226—Mixtures of di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
Definitions
- the present invention relates to a polymerizable composition and a cured product of the polymerizable composition.
- Cationic polymerizable compositions are used in fields such as inks, paints, various coating agents, adhesives, and optical members.
- Patent Documents 1 to 3 below disclose cationically polymerizable compositions used as various photocurable adhesives.
- an object of the present invention is to provide a polymerizable composition from which a cured product having excellent resistance to moist heat can be produced.
- the present invention provides a polymerizable composition containing a thioether compound (A), a cationic polymerizable compound (B) and a cationic polymerization initiator (C).
- the present invention also provides a photocurable adhesive containing the above polymerizable composition.
- the present invention also provides a method for producing a cured product, which comprises the step of irradiating the polymerizable composition with an active energy ray or the step of heating.
- the present invention also provides a cured product of the polymerizable composition.
- the present invention provides use of the polymerizable composition as a photocurable adhesive.
- the polymerizable composition of the present invention it is possible to produce a cured product with excellent moist heat resistance.
- the polymerizable composition of the present invention will be described in detail below.
- the polymerizable composition of the present invention contains a thioether compound (A).
- the cured product of the polymerizable composition has excellent moisture and heat resistance. Furthermore, this cured product has excellent heat resistance, adhesiveness, and optical properties.
- a thioether compound (A) is a compound having a thioether bond in its molecule.
- known thioether compounds can be used without particular limitation as the thioether compound (A).
- the cured product of the polymerizable composition has better moist heat resistance, and the cured product also has better heat resistance and adhesiveness. Therefore, it is possible to use a thioether compound having an ester bond in the molecule. preferable.
- a compound having a group represented by the following general formula (I) provides a cured product of the polymerizable composition with better moist heat resistance and heat resistance of the cured product. It is preferable because it also has good properties and adhesiveness.
- R 1 is an optionally substituted aliphatic hydrocarbon group having 1 to 30 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, A ring-containing group, a group in which one or more methylene groups in the aliphatic hydrocarbon group having 1 to 30 carbon atoms are substituted with a divalent group selected from ⁇ Group A> below, or the above 6 carbon atoms represents a group in which one or more of the methylene groups in the aromatic hydrocarbon ring-containing group of to 30 is substituted with a divalent group selected from the following ⁇ group A>, Y 1 is a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, or one or more of the methylene groups in the divalent hydrocarbon group having 1 to 30 carbon atoms is the following represents a group substituted with a divalent group selected from ⁇ Group A>, * represents a bond.
- the aliphatic hydrocarbon group having 1 to 30 carbon atoms represented by R 1 in general formula (I) includes an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a carbon atom Alkynyl groups having 2 to 30 carbon atoms, cycloalkyl groups having 3 to 30 carbon atoms, and the like can be mentioned.
- the alkyl group having 1 to 30 carbon atoms represented by R 1 may be linear or branched.
- Linear alkyl groups include, for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, henicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group and triacontyl group etc.
- Examples of the branched alkyl group include groups in which one or more of the straight-chain alkyl groups are substituted with an alkyl group having 1 to 9 carbon atoms, specifically a 1,3-dimethylbutyl group. , 1-isopropylpropyl group, 1,2-dimethylbutyl group, 2-heptyl group, 1,4-dimethylpentyl group, tert-heptyl group, 2-methyl-1-isopropylpropyl group, 1-ethyl-3-methylbutyl group, isooctyl group, tert-octyl group, 2-ethylhexyl group, 2-methylhexyl group, 2-propylhexyl group, isononyl group, isodecyl group, isoundecyl group and isododecyl group.
- the alkyl group having 1 to 9 carbon atoms include those having 1 to 9 carbon atoms among the alkyl groups having 1 to 30 carbon atoms represented by R 1 .
- the cured product of the polymerizable composition has better moist heat resistance, and the cured product also has better heat resistance, adhesiveness, and optical properties. ⁇ 23 is preferred, 5-20 is more preferred, 7-17 is even more preferred, and 9-15 is even more preferred. From the same point of view, the alkyl group is preferably linear.
- alkenyl groups having 2 to 30 carbon atoms represented by R 1 include ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group, icosenyl group, henicosenyl group, docosenyl group, tricosenyl group, tetracocenyl group, pentacosenyl group, hexacosenyl group, heptacosenyl group, octacocenyl group , nonacosenyl
- the alkynyl group having 2 to 30 carbon atoms represented by R 1 includes ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group and 1-octynyl group. , 1-decynyl group, 1-octadecynyl group and the like.
- the cycloalkyl group having 3 to 30 carbon atoms represented by R 1 includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclooctadecyl, 2-bornyl, 2 -isobornyl group, 1-adamantyl group and the like.
- an aromatic-hydrocarbon-ring-containing group means a group having an aromatic-hydrocarbon ring.
- the aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms represented by R 1 may have a monocyclic structure or a polycyclic structure.
- the aromatic-hydrocarbon-ring-containing group having a polycyclic structure may have a condensed ring structure or two aromatic hydrocarbon rings linked together.
- the aromatic hydrocarbon ring-containing group in which two aromatic hydrocarbon rings are linked may be one in which two monocyclic aromatic hydrocarbon rings are linked, and a monocyclic aromatic hydrocarbon ring and an aromatic hydrocarbon ring having a condensed ring structure may be linked, or two aromatic hydrocarbon rings having a condensed ring structure may be linked.
- the linking group for linking the two aromatic hydrocarbon rings may be any group as long as the group containing the aromatic hydrocarbon ring as a whole can have aromaticity. Single bonds, sulfide groups (-S- ) and a carbonyl group. Examples of monocyclic aromatic hydrocarbon rings include benzene, toluene, ethylbenzene and 2,4,6-trimethylbenzene. Examples of aromatic hydrocarbon rings having a condensed ring structure include naphthalene, anthracene, phenanthrene, and pyrene.
- the aromatic hydrocarbon ring-containing group in which two aromatic hydrocarbon rings are linked examples include groups in which monocyclic aromatic hydrocarbon rings are linked, such as diphenyl sulfide and benzoylphenyl.
- the number of carbon atoms in the aromatic hydrocarbon ring is preferably 6 to 20 from the viewpoint that the cured product of the polymerizable composition has better resistance to heat and humidity.
- the number of carbon atoms in the aromatic hydrocarbon ring is more preferably 6 to 15 from the viewpoint of improving the heat resistance, adhesiveness, and optical properties of the cured product in addition to the heat and humidity resistance.
- the divalent hydrocarbon group having 1 to 30 carbon atoms represented by Y 1 is an optionally substituted aliphatic hydrocarbon group having 1 to 30 carbon atoms represented by R 1 or A divalent group obtained by removing one hydrogen atom from an optionally substituted aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms can be mentioned.
- hydrocarbon groups having 1 to 30 carbon atoms represented by R 2 and R 3 in Group A include aliphatic hydrocarbon groups having 1 to 30 carbon atoms and aromatic hydrocarbon groups having 6 to 30 carbon atoms.
- a hydrocarbon ring-containing group can be mentioned.
- the aliphatic hydrocarbon group having 1 to 30 carbon atoms represented by R 2 and R 3 includes the same aliphatic hydrocarbon groups having 1 to 30 carbon atoms as represented by R 1 .
- the aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms represented by R 2 and R 3 is the same as the aromatic hydrocarbon ring containing group having 6 to 30 carbon atoms represented by R 1 . is mentioned.
- the number of carbon atoms in the groups defined in the present invention includes the number of carbon atoms in the substituents.
- a methylphenyl group is an aromatic hydrocarbon ring-containing group having 7 carbon atoms.
- the number of carbon atoms in a group in which one or more methylene groups are substituted with a divalent group selected from ⁇ Group A>, as defined in the present invention includes the number of carbon atoms in the divalent group.
- a group in which one methylene group in an alkyl group having 10 carbon atoms is replaced with -COO- has 10 carbon atoms.
- a group in which one methylene group in an alkyl group having 10 carbon atoms is replaced with -O- has 9 carbon atoms.
- one or more methylene groups are bivalent selected from ⁇ group A1>, ⁇ group B>, ⁇ group C>, ⁇ group D>, ⁇ group E>, ⁇ group F> or ⁇ group G> described later The same applies to the number of carbon atoms in the group substituted by the group.
- R 1 in general formula (I) may have a substituent having 5 to 20 carbon atoms. It is preferably an aliphatic hydrocarbon group or an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms which may have a substituent, and an aliphatic hydrocarbon group having 5 to 20 carbon atoms is more preferred, and an alkyl group having 5 to 20 carbon atoms is even more preferred. From the same point of view, the alkyl group having 5 to 20 carbon atoms is preferably linear. From the viewpoint of compatibility, the alkyl group having 5 to 20 carbon atoms preferably has no substituents.
- Y 1 in the general formula (I) has 1 to 1 carbon atoms which may have a substituent. It is preferably a divalent hydrocarbon group of 10, an optionally substituted alkylene group having 1 to 10 carbon atoms or an optionally substituted arylene group having 1 to 10 carbon atoms groups are more preferred. From the same point of view, the alkylene group having 1 to 10 carbon atoms and the arylene group having 1 to 10 carbon atoms preferably have no substituent.
- the number of carbon atoms in the alkylene group is preferably 1 to 8, more preferably 2 to 6, from the viewpoint of compatibility between the heat resistance and compatibility of the cured product of the polymerizable composition.
- the alkylene group is preferably linear.
- the number of groups represented by general formula (I) in the compound may be one, or a plurality of may be
- the adhesiveness and heat resistance of the cured product of the polymerizable composition are good, and the thioether compound preferably has a plurality of groups represented by the general formula (I) in the molecule, and more preferably has 2 to 8. It is preferable to have 2 to 6, and it is particularly preferable to have 2 to 4.
- thioether compound having a group represented by general formula (I) for example, a compound represented by general formula (IA) below can be used.
- R 1 is an optionally substituted aliphatic hydrocarbon group having 1 to 30 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, A ring-containing group, a group in which one or more methylene groups in the aliphatic hydrocarbon group having 1 to 30 carbon atoms are substituted with a divalent group selected from ⁇ Group A> below, or the above 6 carbon atoms represents a group in which one or more of the methylene groups in the aromatic hydrocarbon ring-containing group of to 30 is substituted with a divalent group selected from the following ⁇ group A>, Y 1 is a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, or one or more of the methylene groups in the divalent hydrocarbon group having 1 to 30 carbon atoms is the following A group substituted with a divalent group selected from ⁇ Group A>, n represents an integer from 1 to 6, D represents an n-valent group.
- the monovalent group represented by D is an aliphatic hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, a substituent
- One or more of the aromatic hydrocarbon ring-containing groups having 6 to 30 carbon atoms and the methylene groups in the aliphatic hydrocarbon groups having 1 to 30 carbon atoms are selected from the following ⁇ group B> A group substituted by a selected divalent group, or one or more of the methylene groups in the aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms is substituted by a divalent group selected from the following ⁇ group B> Substituted groups are included.
- an optionally substituted aliphatic hydrocarbon group having 1 to 30 carbon atoms represented by R 1 described above and an optionally substituted carbon Examples thereof include the same aromatic hydrocarbon ring-containing groups having 6 to 30 atoms.
- the hydrocarbon groups having 1 to 30 carbon atoms represented by R 20 and R 30 in ⁇ Group B> include the above-described hydrocarbon groups having 1 to 30 carbon atoms represented by R 2 and R 3 . The same can be mentioned.
- examples of the divalent group represented by D include groups represented by the following formula (1).
- Y 10 is a single bond, —CO—, —NR 200 —, —S—, a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, or the carbon atom represents a group in which one or more of the methylene groups in the divalent hydrocarbon group of numbers 1 to 30 is substituted with a divalent group selected from the following ⁇ group C>,
- R 200 represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms
- Z 1 and Z 2 each independently have a direct bond
- —CO— an optionally substituted divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, or a substituent
- * represents a bond.
- the optionally substituted divalent hydrocarbon group having 1 to 30 carbon atoms represented by Y 10 in formula (1) the above-mentioned Y 1 represented by 1 to Those similar to the divalent hydrocarbon group of 30 can be mentioned.
- the hydrocarbon group having 1 to 30 carbon atoms represented by R 200 , R 21 and R 31 in formula (1) includes the carbonized hydrocarbon groups having 1 to 30 carbon atoms represented by R 2 and R 3 described above. The same as the hydrogen group can be mentioned.
- a substituent represented by R 1 A divalent group obtained by removing one hydrogen atom from an aliphatic hydrocarbon group having 1 to 30 carbon atoms which may have
- the optionally substituted divalent aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms represented by Z 1 and Z 2 in formula (1) is represented by R 1
- a divalent group obtained by removing one hydrogen atom from an optionally substituted aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms can be mentioned.
- examples of the trivalent group represented by D include groups represented by the following formula (2).
- Y 11 is an optionally substituted trivalent hydrocarbon group having 1 to 30 carbon atoms or a methylene group in the trivalent hydrocarbon group having 1 to 30 carbon atoms.
- one or more represents a group substituted with a divalent group selected from the following ⁇ group D>
- Z 1 , Z 2 and Z 3 are each independently a direct bond, —CO—, an optionally substituted divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, or a represents a divalent aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms which may be * represents a bond.
- the optionally substituted trivalent hydrocarbon group having 1 to 30 carbon atoms represented by Y 11 in formula (2) the above-mentioned Y 1 represented by 1 to A trivalent group obtained by further removing one hydrogen atom from the 30 divalent hydrocarbon group is exemplified.
- hydrocarbon group having 1 to 30 carbon atoms represented by R 24 and R 34 in formula (4) the hydrocarbon group having 1 to 30 carbon atoms represented by R 2 and R 3 described above and The same can be mentioned.
- the divalent aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms represented by Z 1 and Z 2 has better moist heat resistance of the cured product of the polymerizable composition, and heat resistance of the cured product. , adhesion and optical properties are also improved, it is preferably a monocyclic aromatic hydrocarbon ring, and more preferably a phenylene group.
- the aromatic hydrocarbon ring-containing group preferably has a substituent.
- an alkyl group having 1 to 10 carbon atoms is preferable. From the viewpoint of compatibility, the alkyl group is preferably branched. Examples of the alkyl group having 1 to 10 carbon atoms include those having 1 to 10 carbon atoms among the alkyl groups having 1 to 30 carbon atoms represented by R 1 described above.
- the content of the thioether compound (A) in the polymerizable composition of the present invention is 100 parts by mass of the cationically polymerizable compound (B), which will be described later, because the cured product of the polymerizable composition has good heat resistance and adhesiveness.
- the thioether compound (A) preferably contains 0.1 parts by mass or more and less than 10 parts by mass, more preferably 0.2 parts by mass or more and less than 5 parts by mass, and 0.3 parts by mass or more and 3 It is more preferably contained in an amount of less than 0.4 parts by mass, and particularly preferably in an amount of 0.4 parts by mass or more and less than 2 parts by mass.
- cationically polymerizable compound (B) known cationically polymerizable compounds can be used without particular limitation.
- cationic polymerizable compounds (B) include epoxy compounds and oxetane compounds (B4).
- the cationically polymerizable compound (B) further improves the moist heat resistance of the polymerizable composition, and also improves the heat resistance and adhesiveness. Therefore, the alicyclic epoxy compound (B1) and the aliphatic epoxy compound (B2) and aromatic epoxy compound (B3).
- Examples of alicyclic epoxy compounds having two cycloalkene oxide structures include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4- Epoxy-1-methylhexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4- epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis(3,4-epoxycyclohexylmethyl)adipate, propane-2, 2-diyl-bis(3,4-epoxycyclohexane), 2,2-bis(3,4-epoxycyclohexyl)prop
- a commercially available product can be used as the aliphatic epoxy compound (B2).
- Examples of commercially available products of the aliphatic epoxy compound (B2) include Denacol EX-121, Denacol EX-171, Denacol EX-192, Denacol EX-211, Denacol EX-212, Denacol EX-313 and Denacol EX-314.
- the cationically polymerizable compound (B) preferably contains an aromatic epoxy compound (B3) since the cured product of the polymerizable composition has good heat resistance.
- the aromatic epoxy compound (B3) is a compound having an aromatic ring and at least one epoxy group.
- the aromatic epoxy compound (B3) may be monofunctional or polyfunctional.
- the aromatic epoxy compound (B3) preferably contains at least a monofunctional aromatic epoxy compound or a bifunctional aromatic epoxy compound, since the cured product of the polymerizable composition has good heat resistance. .
- oxetane compound (B4) A commercially available product can also be used as the oxetane compound (B4).
- Commercially available oxetane compounds include, for example, Aron oxetane OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211, OXT-212 (manufactured by Toagosei), Ethanacol OXBP, OXTP (Ube Industries) made) and the like.
- the photocationic polymerization initiator may be any compound that can release a substance that initiates cationic polymerization upon irradiation with light, and is an onium salt that releases a Lewis acid upon irradiation with light. Double salts, or derivatives thereof, are preferred.
- the cation [A] m+ is onium, and its structure can be represented, for example, by the following general formula.
- [(R 110 ) x Q] m+ (ii) R 110 represents an organic group having 1 to 60 carbon atoms and optionally containing any number of atoms other than carbon atoms.
- x represents an integer of 1 to 5; Each of the x R 110 is independent and may be the same or different. At least one of x R 110 represents the above organic group having an aromatic ring.
- the curability of the polymerizable composition is improved, and the adhesiveness of the cured product of the polymerizable composition is improved.
- Preferred are sulfonium salts of sulfonium cations, such as the triphenylsulfonium cation described above, with anions such as hexafluorophosphate, hexafluoroantimonate, tetrakis(pentafluorophenyl)borate, and the like.
- thermal cationic polymerization initiators include, for example, Adeka Opton CP-77, Adeka Opton CP-66 (manufactured by ADEKA), CI-2639, CI-2624 (Nippon Soda), San-Aid SI-60, San-Aid SI-80 and San-Aid. SI-100 (manufactured by Sanshin Chemical Industry) and the like.
- solvents examples include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1 , 2-diethoxyethane, propylene glycol monomethyl ether, dipropylene glycol dimethyl ether and other ether solvents; methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, succinic acid Ester solvents such as dimethyl and texanol; Cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoeth
- the total amount of optional components other than the thioether compound (A), the cationic polymerizable compound (B) and the cationic polymerization initiator (C) in the polymerizable composition of the present invention depends on the application of the present invention, etc. From the viewpoint of further enhancing the effects of the invention, it is preferably 20 parts by mass or less, particularly 10 parts by mass or less per 100 parts by mass of the cationic polymerizable compound (A).
- the polymerizable composition of the present invention is a combination of a thioether compound (A), a cationic polymerizable compound (B) and a cationic polymerization initiator (C). Even if the thioether compound (A) is combined with the radically polymerizable composition and the radical polymerization initiator, the effect of the present invention that a cured product having good moisture and heat resistance can be obtained is not exhibited. Furthermore, the cured product of the polymerizable composition containing the radically polymerizable composition and the radical polymerization initiator has poor adhesiveness. Therefore, the polymerizable composition of the present invention preferably does not contain a radically polymerizable composition and a radical polymerization initiator.
- a radically polymerizable composition is a radically polymerizable compound.
- the radically polymerizable compound include compounds having an ethylenically unsaturated group such as an acrylic group, a methacrylic group, and a vinyl group.
- radically polymerizable compounds described in International Publication No. 2018/012383, radically polymerizable organic substances described in International Publication No. 2014/021023, and the like are included.
- Lens parts of lens sheets such as Fresnel lens sheets and lenticular lens sheets, or backlights using such sheets, optical lenses such as microlenses, optical elements, optical connectors, optical waveguides, optical molding Casting agents and the like can be mentioned, and examples of substrates that can be applied as coating agents include metals, wood, rubber, plastics, glass, ceramic products, and the like.
- the polymerizable composition of the present invention uses a combination of a thioether compound (A), a cationic polymerizable compound (B) and a cationic polymerization initiator (C), so that the cured product thereof has excellent moisture and heat resistance. becomes.
- the polymerizable composition of the present invention is excellent in heat resistance, adhesiveness and optical properties by using these components in combination. Therefore, the polymerizable composition of the present invention is particularly useful as an adhesive, especially a photocurable adhesive.
- the photocurable adhesive of the invention contains the polymerizable composition of the invention. Since the photocurable adhesive of the present invention contains the polymerizable composition of the present invention, it has excellent moist heat resistance. In addition to this, the photocurable adhesive of the present invention is also excellent in heat resistance, adhesiveness and optical properties.
- the polymerizable composition of the present invention as a photocurable adhesive
- the polymerizable composition described above is used as a photocurable adhesive for bonding two members by irradiation with light.
- the present invention also provides a method of adhering two members with the polymerizable composition described above. Specifically, after disposing the polymerizable composition between two members, the polymerizable composition is irradiated with light to cure the polymerizable composition and bond the two members together.
- B1-1 compound represented by the following formula (B1-1)
- B1-2 compound represented by the following formula (B1-2)
- B2-1 represented by the following formula (B2-1)
- Compound B2-2 Compound B3-1 represented by the following formula (B2-2): Compound B3-2 represented by the following formula (B3-1): Compound B3-2 represented by the following formula (B3-2)
- Compound B3-3 Compound B3-4 represented by the following formula (B3-3):
- Compound B4-2 a compound represented by the following formula (B4-2)
- C-1 50% by mass propylene carbonate solution of a compound represented by the following formula (C1-2)
- C-2 50% by mass propylene carbonate solution of a compound represented by the following formula (C2)
- the laminate was irradiated with light corresponding to 1000 mJ/cm 2 through the COP film, and adhered to prepare a test piece.
- the obtained test piece was stored under conditions of 30° C., 50% RH and atmospheric pressure for 12 hours after exposure. Then, a 2.0 cm wide piece was cut from the test piece to obtain a sample for evaluation.
- the obtained sample was subjected to a 90 degree peel test, and the adhesiveness of the evaluation sample was evaluated according to the following criteria.
- the 90 degree peel test was performed under conditions of 30°C, 50% RH and atmospheric pressure. The larger the value of N/2cm, the better the adhesiveness.
- ⁇ Heat resistance test> A test piece was obtained in the same manner as in the optical property test. The b* of the obtained test piece was measured using an ultraviolet-visible-near-infrared spectrophotometer V-670 (manufactured by JASCO Corporation). Then, the test piece was held in an environment of 85° C. and 85% RH for 500 hours, and then b* of the test piece was measured. Then, the heat resistance of the test piece was evaluated according to the following criteria. The smaller the ⁇ b*, the better the heat resistance. A: ⁇ b* ⁇ 3 B: 3 ⁇ b* ⁇ 5 C: 5 ⁇ b* ⁇ 8 D: 8 ⁇ b*
- the cured products of the polymerizable compositions of Examples 1 to 21 had good moist heat resistance. These cured products were also excellent in heat resistance, adhesion and optical properties.
- the cured product of the polymerizable composition of Comparative Example 1 containing no thioether compound (A) was poor in heat resistance as well as resistance to heat and humidity.
- the cured product of the polymerizable composition of Comparative Example 2 containing the other component (A'-1) in place of the thioether compound (A) had poor heat and humidity resistance, as well as poor heat resistance and optical properties.
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Abstract
Description
すなわち本発明は、チオエーテル化合物(A)、カチオン重合性化合物(B)及びカチオン重合開始剤(C)を含有する重合性組成物を提供するものである。
また本発明は、前記重合性組成物に対して、活性エネルギー線を照射する工程、又は加熱する工程を含む、硬化物の製造方法を提供するものである。
また本発明は、前記重合性組成物の硬化物を提供するものである。
更に本発明は、前記重合性組成物の光硬化性接着剤としての使用を提供するものである。
本発明の重合性組成物は、チオエーテル化合物(A)を含有する。チオエーテル化合物(A)を含有することによって、重合性組成物の硬化物は耐湿熱性に優れたものとなる。更にこの硬化物は、耐熱性、接着性、及び光学特性にも優れたものとなる。
Y1は、置換基を有してもよい炭素原子数1~30の2価の炭化水素基又は該炭素原子数1~30の2価の炭化水素基中のメチレン基の1つ以上が下記<群A>より選ばれる2価の基により置換された基を表し、
*は結合手を表す。
<群A>:-O-、-CO-、-COO-、-OCO-、-NR2-、-NR3CO-又は-S-
R2及びR3は、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。)
本発明においては、重合性組成物の硬化物の耐湿熱性が一層良好となり、且つ該硬化物の耐熱性、接着性、及び光学特性も良好となることから、アルキル基の炭素原子数は、5~23であることが好ましく、5~20であることがより好ましく、7~17であることが更に好ましく、9~15であることがより一層好ましい。また同様の観点から、アルキル基は直鎖状であることが好ましい。
R1で表される炭素原子数6~30の芳香族炭化水素環含有基は、単環構造であってもよく、多環構造であってもよい。多環構造の芳香族炭化水素環含有基は、縮合環構造であってもよく、2つの芳香族炭化水素環が連結したものであってもよい。
2つの芳香族炭化水素環が連結した芳香族炭化水素環含有基としては、2つの単環構造の芳香族炭化水素環が連結したものであってもよく、単環構造の芳香族炭化水素環と縮合環構造の芳香族炭化水素環とが連結したものであってもよく、2つの縮合環構造の芳香族炭化水素環が連結したものであってもよい。
2つの芳香族炭化水素環を連結する連結基としては、芳香族炭化水素環含有基全体として芳香族性を有するものとすることができるものであればよく、単結合、スルフィド基(-S-)及びカルボニル基等が挙げられる。
単環構造の芳香族炭化水素環としては、例えば、ベンゼン、トルエン、エチルベンゼン、2,4,6-トリメチルベンゼン等が挙げられる。
縮合環構造の芳香族炭化水素環としては、例えば、ナフタレン、アントラセン、フェナントレン、ピレン等が挙げられる。
2つの芳香族炭化水素環が連結した芳香族炭化水素環含有基としては、例えば、ジフェニルスルフィド、ベンゾイルフェニル等の単環構造の芳香族炭化水素環が連結した基が挙げられる。
重合性組成物の硬化物の耐湿熱性が一層良好となる観点から、本発明において芳香族炭化水素環の炭素原子数は6~20であることが好ましい。耐湿熱性に加えて、硬化物の耐熱性、接着性、及び光学特性も良好となる観点から、芳香族炭化水素環の炭素原子数は6~15であることがより好ましい。
R2及びR3で表される炭素原子数1~30の脂肪族炭化水素基としては、R1で表される炭素原子数1~30の脂肪族炭化水素基と同様のものが挙げられる。
R2及びR3で表される炭素原子数6~30の芳香族炭化水素環含有基としては、R1で表される炭素原子数6~30の芳香族炭化水素環含有基と同様のものが挙げられる。
また本発明で規定する、メチレン基の1つ以上が<群A>より選ばれる2価の基により置換された基の炭素原子数は、2価の基の炭素原子数を含める。例えば、炭素原子数10のアルキル基中の1つのメチレン基が-COO-で置換された基の炭素原子数は10とする。また、炭素原子数10のアルキル基中の1つのメチレン基が-O-で置換された基の炭素原子数は9とする。メチレン基の1つ以上が、後述する<群A1>、<群B>、<群C>、<群D>、<群E>、<群F>又は<群G>より選ばれる2価の基により置換された基の炭素原子数についても同様である。
Y1は、置換基を有してもよい炭素原子数1~30の2価の炭化水素基又は該炭素原子数1~30の2価の炭化水素基中のメチレン基の1つ以上が下記<群A>より選ばれる2価の基により置換された基であり、
nは1~6の整数を表し、
Dはn価の基を表す。
<群A>:-O-、-CO-、-COO-、-OCO-、-NR2-、-NR3CO-又は-S-
R2及びR3は、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。)
R20及びR30は、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。
R200は水素原子又は炭素原子数1~30の炭化水素基を表し、
Z1及びZ2はそれぞれ独立に、直接結合、-CO-、置換基を有していてもよい炭素原子数1~30の2価の脂肪族炭化水素基、又は置換基を有していてもよい炭素原子数6~30の2価の芳香族炭化水素環含有基を表し、
*は結合手を表す。
<群C>:-O-、-CO-、-COO-、-OCO-、-NR21-、-NR31CO-又は-S-
R21及びR31は、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。)
Z1、Z2及びZ3はそれぞれ独立に、直接結合、-CO-、置換基を有していてもよい炭素原子数1~30の2価の脂肪族炭化水素基、又は置換基を有していてもよい炭素原子数6~30の2価の芳香族炭化水素環含有基を表し、
*は結合手を表す。
<群D>:-O-、-CO-、-COO-、-OCO-、-NR22-、-NR32CO-又は-S-
R22及びR32は、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。)
Z1、Z2、Z3及びZ4はそれぞれ独立に、直接結合、-CO-、置換基を有していてもよい炭素原子数1~30の2価の脂肪族炭化水素基、又は置換基を有していてもよい炭素原子数6~30の2価の芳香族炭化水素環含有基を表し、
*は結合手を表す。
<群E>:-O-、-CO-、-COO-、-OCO-、-NR23-、-NR33CO-又は-S-
R23及びR33は、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。)
Z1、Z2、Z3、Z4及びZ5はそれぞれ独立に、直接結合、-CO-、置換基を有していてもよい炭素原子数1~30の2価の脂肪族炭化水素基、又は置換基を有していてもよい炭素原子数6~30の2価の芳香族炭化水素環含有基を表し、
*は結合手を表す。
<群F>:-O-、-CO-、-COO-、-OCO-、-NR24-、-NR34CO-又は-S-
R24及びR34は、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。)
Z1、Z2、Z3、Z4、Z5及びZ6はそれぞれ独立に、直接結合、-CO-、置換基を有していてもよい炭素原子数1~30の2価の脂肪族炭化水素基、又は置換基を有していてもよい炭素原子数6~30の2価の芳香族炭化水素環含有基を表し、
*は結合手を表す。
<群G>:-O-、-CO-、-COO-、-OCO-、-NR25-、-NR35CO-又は-S-
R25及びR35は、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。)
Z1及びZ2で表される炭素原子数1~30の2価の脂肪族炭化水素基は、重合性組成物の硬化物の耐湿熱性が一層良好となり、且つ該硬化物の耐熱性、接着性、及び光学特性も良好となることから、炭素原子数1~30のアルキレン基であることが好ましい。同様の観点から、当該アルキレン基は直鎖状であることが好ましい。また当該アルキレン基は置換基を有さないことが好ましい。更に当該アルキレン基の炭素原子数は、相溶性の観点から、1~10であることが好ましく、1~4であることがより好ましい。
Z1及びZ2で表される炭素原子数6~30の2価の芳香族炭化水素環含有基は、重合性組成物の硬化物の耐湿熱性が一層良好となり、且つ該硬化物の耐熱性、接着性、及び光学特性も良好となることから、単環構造の芳香族炭化水素環であることが好ましく、フェニレン基であることがより好ましい。また当該芳香族炭化水素環含有基は置換基を有することが好ましい。当該置換基としては、炭素原子数1~10のアルキル基が好ましい。当該アルキル基は、相溶性の観点から、分岐状であることが好ましい。炭素原子数1~10のアルキル基としては、上述したR1で表される炭素原子数1~30のアルキル基のうちの炭素原子数1~10のものが挙げられる。
式(3)中のZ1、Z2、Z3及びZ4は直接結合であることが好ましい。
n1は1~6の整数を表し、
D1は、置換基を有していてもよい炭素原子数6~30の芳香族炭化水素環含有基又は置換基を有していてもよい炭素原子数6~30の芳香族炭化水素環含有基中のメチレン基の1つ以上が下記<群A1>より選ばれる2価の基により置換された基を表す。
<群A1>:-O-、-CO-、-COO-、-OCO-、-NR2a-、-NR3aCO-又は-S-
R2a及びR3aは、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。)
重合性組成物の硬化物の耐湿熱性が一層良好となり、且つ該硬化物の耐熱性、接着性、及び光学特性も良好となることから、前記一般式(I-B)中のn1は1~4であることが好ましく、2~3であることがより好ましい。
重合性組成物の硬化物の耐湿熱性が一層良好となり、且つ該硬化物の耐熱性、接着性、及び光学特性も良好となることから、前記一般式(I-B)中のD1で表される芳香族炭化水素環含有基は、単環構造の芳香族炭化水素環を有することが好ましく、フェニル基であることがより好ましい。当該芳香族炭化水素環含有基の炭素原子数は、6~20であることが好ましく、6~16がより好ましく、6~110が更に好ましい。また当該芳香族炭化水素環含有基は、重合性組成物の硬化物の耐熱性が良好となることから、置換基を有することが好ましい。当該置換基としては、相溶性の観点から、炭素原子数1~10、特に炭素原子数1~4のアルキル基又は水酸基が好ましく、芳香族炭化水素環含有基がアルキル基及び水酸基で置換されていることがより好ましい。当該炭素原子数1~10のアルキル基としては、上述したR1で表される炭素原子数1~30のアルキル基のうちの炭素原子数1~10のものが挙げられる。
本発明においてカチオン重合性化合物とは、光照射又は加熱により活性化したカチオン重合開始剤により高分子化、又は架橋反応を起こす化合物を意味する。
シクロアルケンオキサイド構造は、シクロヘキセン環含有化合物やシクロペンテン環含有化合物を酸化剤でエポキシ化することによって得られる、シクロヘキセンオキサイド構造やシクロペンテンオキサイド構造のように、脂肪族環とエポキシ環とが環構造の一部を共有する構造である。
カチオン重合性化合物(B)における脂環式エポキシ化合物(B1)の含有量は、重合性組成物の硬化物の耐熱性及び接着性が良好となることから、カチオン重合性化合物(B)100質量部中に、脂環式エポキシ化合物(B1)を1~20質量部含有することが好ましく、3~10質量部含有することがより好ましい。
カチオン重合性化合物(B)における脂肪族エポキシ化合物(B2)の含有量は、重合性組成物の硬化物の耐熱性及び接着性が良好となることから、カチオン重合性化合物(B)100質量部中に、脂肪族エポキシ化合物(B2)を20~60質量部含有することが好ましく、30~50質量部含有することがより好ましい。
芳香族エポキシ化合物(B3)は、芳香族環及び少なくとも1つのエポキシ基を有する化合物である。芳香族エポキシ化合物(B3)は単官能であってもよく、多官能であってもよい。本発明においては、重合性組成物の硬化物の耐熱性が良好となることから、芳香族エポキシ化合物(B3)は少なくとも単官能芳香族エポキシ化合物又は2官能の芳香族エポキシ化合物を含むことが好ましい。
多官能芳香族エポキシ化合物としては、例えば、ビスフェノールA、ビスフェノールF、又はこれらに更にアルキレンオキサイドを付加した化合物のグリシジルエーテル化物;レゾルシノールやハイドロキノン、カテコール等の2個以上のフェノール性水酸基を有する芳香族化合物のグリシジルエーテル;ベンゼンジメタノールやベンゼンジエタノール、ベンゼンジブタノール等のアルコール性水酸基を2個以上有する芳香族化合物のポリグリシジルエーテル化物;フタル酸、テレフタル酸、トリメリット酸等の2個以上のカルボン酸を有する多塩基酸芳香族化合物のグリシジルエステル等が挙げられる。
カチオン重合性化合物(B)における芳香族エポキシ化合物(B3)の含有量は、重合性組成物の硬化物の耐熱性及び接着性が良好となることから、カチオン重合性化合物(B)100質量部中に、芳香族エポキシ化合物(B3)を30~70質量部含有することが好ましく、40~60質量部含有することがより好ましい。
オキセタン化合物(B4)は、少なくとも1つのオキセタニル基を有し、エポキシ基を有しない化合物である。本発明においては、重合性組成物の硬化物の耐湿熱性が一層良好となることから、オキセタニル基を1つ又は2つ有するオキセタン化合物を用いることが好ましい。
カチオン重合性化合物(B)におけるオキセタン化合物(B4)の含有量は、重合性組成物の硬化物の耐湿熱性が一層良好となり、且つ該硬化物の耐熱性及び接着性が良好となることから、カチオン重合性化合物(B)100質量部中に、オキセタン化合物(B4)を1~30質量部含有することが好ましく、5~25質量部含有することがより好ましい。
本発明において、カチオン重合開始剤(C)とは、光の照射又は加熱によりカチオン重合を開始させる物質を放出させることが可能な化合物である。
本発明においては、カチオン重合開始剤(C)として、光カチオン重合開始剤又は熱カチオン重合開始剤を用いることができる。本発明においては、硬化収縮が少なくて接着性に優れることから、カチオン重合開始剤(C)は光カチオン重合開始剤を用いることが好ましい。
[A]m+[B]m- (i)
[(R110)xQ]m+ (ii)
前記一般式(ii)中、R110は炭素原子数が1~60であり、炭素原子以外の原子をいくつ含んでいてもよい有機基を表す。
xは1~5の整数を表す。
x個のR110は各々独立で、同一でも異なっていてもよい。
x個のR110のうち、少なくとも1つが、芳香族環を有する前記有機基を表す。
QはS、N、Se、Te、P、As、Sb、Bi、O、I、Br、Cl、F及びN=Nからなる群から選ばれる原子又は原子団を表す。また、陽イオン[A]m+中のQの原子価をqとしたとき、m=x-qなる関係が成り立つことが必要である。ただし、N=Nは原子価0として扱う。
[LXy]m- (iii)
前記一般式(iii)中、Lはハロゲン化物錯体の中心原子である金属又は半金属(Metalloid)を表し、B、P、As、Sb、Fe、Sn、Bi、Al、Ca、In、Ti、Zn、Sc、V、Cr、Mn又はCoである。
Xはハロゲン原子を表す。
yは3~7の整数を表す。また、陰イオン[B]m-中のLの原子価をpとしたとき、m=y-pなる関係が成り立つことが必要である。
[LXy-1(OH)]m- (iv)
ここで、L、X及びbは前記と同様である。
また、その他の陰イオンとしては、過塩素酸イオン(ClO4)-、トリフルオロメチル亜硫酸イオン(CF3SO3)-、フルオロスルホン酸イオン(FSO3)-、トルエンスルホン酸陰イオン、トリニトロベンゼンスルホン酸陰イオン、カンファースルフォネート、ノナフロロブタンスルフォネート、ヘキサデカフロロオクタンスルフォネート、テトラアリールボレート、テトラキス(ペンタフルオロフェニル)ボレート等が挙げられる。
本発明の重合性組成物は、チオエーテル化合物(A)と、カチオン重合性化合物(B)及びカチオン重合開始剤(C)とを組合せて用いることによって、その硬化物が、耐湿熱性に優れたものとなる。これに加えて本発明の重合性組成物は、これらの成分を組合せて用いることで、耐熱性、接着性、及び光学特性にも優れたものとなる。したがって本発明の重合性組成物は接着剤、特に光硬化性接着剤として特に有用である。
本発明の光硬化性接着剤は本発明の重合性組成物を含有する。本発明の光硬化性接着剤は、本発明の重合性組成物を含有するので、耐湿熱性に優れたものとなる。これに加えて本発明の光硬化性接着剤は、耐熱性、接着性、及び光学特性にも優れたものとなる。
本発明の硬化物は、本発明の重合性組成物の硬化物であり、該重合性組成物に対して、活性エネルギー線を照射するか、或いは該重合性組成物を加熱することによって製造することができる。活性エネルギー線を照射条件及び加熱条件に制限はなく、公知の条件を採用することができる。
本発明においては、上述の重合性組成物を、光の照射によって2つの部材を接着するための光硬化性接着剤として使用する。重合性組成物の使用量、部材への適用方法、照射する光の波長や照射量等に特に制限はなく、公知の方法や条件を適宜採用することができる。また本発明によれば、2つの部材を上述の重合性組成物によって接着する方法も提供される。具体的には、2つの部材の間に上述の重合性組成物を配した後、該重合性組成物に光を照射して重合性組成物を硬化させて2つの部材を接着する。
下記の表1~3に示す配合で各成分を十分に混合して、実施例1~21の重合性組成物1~21、並びに比較例1及び2の重合性組成物を調製した。表中の符号は下記の成分を意味する。また、表中の数値は質量部を表す。
A-2:下記の式(A-2)で表される化合物
A-3:下記の式(A-3)で表される化合物
A-4:下記の式(A-4)で表される化合物
A-5:下記の式(A-5)で表される化合物
A-6:下記の式(A-6)で表される化合物
A-7:下記の式(A-7)で表される化合物
A’-1:下記の式(A’-1)で表される化合物
B1-2:下記の式(B1-2)で表される化合物
B2-1:下記の式(B2-1)で表される化合物
B2-2:下記の式(B2-2)で表される化合物
B3-1:下記の式(B3-1)で表される化合物
B3-2:下記の式(B3-2)で表される化合物
B3-3:下記の式(B3-3)で表される化合物
B3-4:下記の式(B3-4)で表される化合物
B4-1:下記の式(B4-1)で表される化合物
B4-2:下記の式(B4-2)で表される化合物
C-2:下記の式(C2)で表される化合物の炭酸プロピレン50質量%溶液
実施例及び比較例で調製した組成物を、硬化後の膜厚が3μmになるようにTACフィルム(富士フイルム(株)製フジタックTD80)にそれぞれ塗布し、塗膜を形成した。次いでコロナ放電処理を施したCOP(シクロオレフィンポリマー、日本ゼオン(株)製:品番ゼオノアフィルム14-060)フィルムを、TACフィルムの塗膜が形成されている面にラミネーターを用いて貼り合わせ、積層体を得た。そして、無電極紫外光ランプを用いて1000mJ/cm2に相当する光をCOPフィルム越しに積層体に照射し、接着することによって試験片を製造した。
得られた試験片を露光から12時間の間、30℃、50%RH、大気圧条件下で保存した。次いで、試験片から2.0cm幅に切り出し、評価用サンプルを得た。得られたサンプルについて、90度ピール試験を行い、下記基準に従って評価用サンプルの接着性を評価した。90度ピール試験は、30℃、50%RH、大気圧条件下で行った。N/2cmの値が大きいほど接着性に優れる。
A:2.5N/2cm以上又は基材破壊
B:1.5N/2cm以上2.5N/2cm未満
C:0.5N/2cm以上、1.5N/2cm未満
D:0.5N/2cm未満。
接着性試験と同様にして試験片を得た。得られた試験片を85℃、85%RHの環境下に500時間保持した。その後試験片を室温に下げたのち、当該試験片に対して、接着性試験と同様にして、90度ピール試験を行い、下記基準に従って評価用サンプルの耐湿熱性を評価した。N/2cmの値が大きいほど耐湿熱性に優れる。
A:1.5N/2cm以上
B:1.0N/2cm以上1.5N/2cm未満
C:0.5N/2cm以上1.0N/2cm未満
D:0.5N/2cm未満
実施例及び比較例で調製した重合性組成物をそれぞれ、硬化後の膜厚が50μmとなるようにガラス板に塗布し、次いで、当該ガラス板の塗膜が形成された面に他のガラス板を貼り合わせた。貼り合わされたガラス板に、高圧Hgランプを用いて1000mJ/cm2のエネルギーを照射し、続いて当該ガラス板を150℃で1時間加熱して、試験片を得た。
得られた試験片のb*を紫外可視近赤外分光光度計V-670(日本分光社製)を用いて測定し、下記の基準で試験片の光学特性を評価した。b*の値が小さいほど光学特性に優れる。
A:硬化物のb*が5未満
B:硬化物のb*が、5以上10未満
C:硬化物のb*が、10以上
光学特性試験と同様にして試験片を得た。得られた試験片のb*を紫外可視近赤外分光光度計V-670(日本分光社製)を用いて測定した。次いで、試験片を85℃、85%RHの環境下に500時間保持した後、試験片のb*を測定した。そして下記の基準で試験片の耐熱性を評価した。△b*が小さいほど耐熱性に優れる。
A:Δb*<3
B:3≦Δb*<5
C:5≦Δb*<8
D:8≦Δb*
Claims (15)
- チオエーテル化合物(A)、カチオン重合性化合物(B)及びカチオン重合開始剤(C)を含有する、重合性組成物。
- チオエーテル化合物(A)が、分子内にエステル結合を有する、請求項1に記載の重合性組成物。
- チオエーテル化合物(A)が下記一般式(I)で表される基を有する、請求項1又は2に記載の重合性組成物。
Y1は、置換基を有してもよい炭素原子数1~30の2価の炭化水素基又は該炭素原子数1~30の2価の炭化水素基中のメチレン基の1つ以上が下記<群A>より選ばれる2価の基により置換された基を表し、
*は結合手を表す。
<群A>:-O-、-CO-、-COO-、-OCO-、-NR2-、-NR3CO-又は-S-、R2及びR3は、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。) - 一般式(I)中のR1が、置換基を有していてもよい炭素原子数5~20の脂肪族炭化水素基又は置換基を有していてもよい炭素原子数6~20の芳香族炭化水素環含有基である、請求項3に記載の重合性組成物。
- 一般式(I)中のY1が、置換基を有していてもよい炭素原子数1~10の2価の炭化水素基である、請求項3又は4に記載の重合性組成物。
- チオエーテル化合物(A)が、分子内に一般式(I)で表される基を複数有する、請求項3~5の何れか一項に記載の重合性組成物。
- チオエーテル化合物(A)が下記一般式(I-B)で表される化合物である、請求項1に記載の重合性組成物。
n1は1~6の整数を表し、
D1は、置換基を有していてもよい炭素原子数6~30の芳香族炭化水素環含有基又は置換基を有していてもよい炭素原子数6~30の芳香族炭化水素環含有基を表す。
<群A1>:-O-、-CO-、-COO-、-OCO-、-NR2a-、-NR3aCO-又は-S-
R2a及びR3aは、それぞれ独立に、水素原子又は炭素原子数1~30の炭化水素基を表す。) - 前記一般式(I-B)中のD1が単環構造の芳香族炭化水素環を有する、請求項7に記載の重合性組成物。
- 前記一般式(I-B)中のR11が、置換基を有していてもよい炭素原子数1~30の脂肪族炭化水素基である、請求項7又は8に記載の重合性組成物。
- チオエーテル化合物(A)を、カチオン重合性化合物(B)100質量部に対して、0.1質量部以上10質量部未満含有する、請求項1~9の何れか一項に記載の重合性組成物。
- カチオン重合性化合物(B)は、脂環式エポキシ化合物(B1)、脂肪族エポキシ化合物(B2)及び芳香族エポキシ化合物(B3)からなる群から選択される少なくとも1種を含有する、請求項1~10の何れか一項に記載の重合性組成物。
- 請求項1~11の何れか一項に記載の重合性組成物を含有する光硬化性接着剤。
- 請求項1~11の何れか一項に記載の重合性組成物に対して、活性エネルギー線を照射する工程、又は加熱する工程を含む、硬化物の製造方法。
- 請求項1~11の何れか一項に記載の重合性組成物の硬化物。
- 請求項1~11の何れか一項に記載の重合性組成物の光硬化性接着剤としての使用。
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2022
- 2022-03-28 WO PCT/JP2022/015169 patent/WO2022210595A1/ja active Application Filing
- 2022-03-28 KR KR1020237025149A patent/KR20230163354A/ko unknown
- 2022-03-28 JP JP2023511299A patent/JPWO2022210595A1/ja active Pending
- 2022-03-28 CN CN202280012229.XA patent/CN116745337A/zh active Pending
- 2022-03-30 TW TW111112102A patent/TW202302754A/zh unknown
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JP2006016411A (ja) * | 2004-05-31 | 2006-01-19 | Jsr Corp | 光学的立体造形用放射線硬化性液状樹脂組成物及びそれを光硬化させて得られる光造形物 |
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JP2008266531A (ja) * | 2007-04-24 | 2008-11-06 | Matsushita Electric Works Ltd | ハロゲンフリーエポキシ樹脂組成物、カバーレイフィルム、ボンディングシート、プリプレグ、プリント配線板用積層板 |
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Publication number | Publication date |
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JPWO2022210595A1 (ja) | 2022-10-06 |
KR20230163354A (ko) | 2023-11-30 |
CN116745337A (zh) | 2023-09-12 |
TW202302754A (zh) | 2023-01-16 |
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