WO2020179287A1 - Acid group-containing (meth)acrylate resin, curable resin composition, cured product, insulating material, resin material for solder resist, and resist member - Google Patents
Acid group-containing (meth)acrylate resin, curable resin composition, cured product, insulating material, resin material for solder resist, and resist member Download PDFInfo
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- WO2020179287A1 WO2020179287A1 PCT/JP2020/002901 JP2020002901W WO2020179287A1 WO 2020179287 A1 WO2020179287 A1 WO 2020179287A1 JP 2020002901 W JP2020002901 W JP 2020002901W WO 2020179287 A1 WO2020179287 A1 WO 2020179287A1
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- 239000002253 acid Substances 0.000 title claims abstract description 289
- 239000004925 Acrylic resin Substances 0.000 title claims abstract description 135
- 229920005989 resin Polymers 0.000 title claims abstract description 50
- 239000011347 resin Substances 0.000 title claims abstract description 50
- 239000011342 resin composition Substances 0.000 title claims abstract description 50
- 239000000047 product Substances 0.000 title claims abstract description 48
- 239000000463 material Substances 0.000 title claims abstract description 17
- 229910000679 solder Inorganic materials 0.000 title claims abstract description 15
- 239000011810 insulating material Substances 0.000 title claims abstract description 8
- 239000003822 epoxy resin Substances 0.000 claims abstract description 163
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 163
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 114
- 238000006243 chemical reaction Methods 0.000 claims abstract description 83
- 150000007519 polyprotic acids Polymers 0.000 claims abstract description 40
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 38
- 239000002994 raw material Substances 0.000 claims abstract description 18
- 125000003700 epoxy group Chemical group 0.000 claims description 48
- 239000003960 organic solvent Substances 0.000 claims description 47
- 239000000376 reactant Substances 0.000 claims description 24
- 239000004593 Epoxy Substances 0.000 claims description 20
- 239000003999 initiator Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 8
- 239000003513 alkali Substances 0.000 abstract description 23
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 22
- 230000036211 photosensitivity Effects 0.000 abstract description 22
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 134
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 114
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 95
- -1 methacryloyl Chemical group 0.000 description 80
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 53
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 50
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 48
- 238000004519 manufacturing process Methods 0.000 description 46
- 239000003054 catalyst Substances 0.000 description 42
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 34
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 34
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- 238000007664 blowing Methods 0.000 description 33
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- 230000015572 biosynthetic process Effects 0.000 description 29
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- ICQFAQGXJAVDED-UHFFFAOYSA-N benzene-1,4-diol;4-(methylamino)phenol Chemical compound OC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ICQFAQGXJAVDED-UHFFFAOYSA-N 0.000 description 20
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 16
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- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
- 150000002596 lactones Chemical class 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
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- 230000003078 antioxidant effect Effects 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- 238000012719 thermal polymerization Methods 0.000 description 8
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 125000004018 acid anhydride group Chemical group 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- 125000005702 oxyalkylene group Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
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- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 125000006353 oxyethylene group Chemical group 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920000193 polymethacrylate Polymers 0.000 description 5
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- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 3
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
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- KVQQRFDIKYXJTJ-UHFFFAOYSA-N naphthalene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C(=O)O)=CC2=C1 KVQQRFDIKYXJTJ-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
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- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- FBOJNMRAZJRCNS-UHFFFAOYSA-M tetraethylphosphanium;chloride Chemical compound [Cl-].CC[P+](CC)(CC)CC FBOJNMRAZJRCNS-UHFFFAOYSA-M 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- NJFUXFRJVIXVSG-UHFFFAOYSA-M tetramethylphosphanium;chloride Chemical compound [Cl-].C[P+](C)(C)C NJFUXFRJVIXVSG-UHFFFAOYSA-M 0.000 description 1
- QBAUHKSMFOSSGE-UHFFFAOYSA-M tetrapropylphosphanium;chloride Chemical compound [Cl-].CCC[P+](CCC)(CCC)CCC QBAUHKSMFOSSGE-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical class NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
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
- C08F290/08—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 side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/144—Polymers containing more than one epoxy group per molecule
-
- 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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F290/08—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 side groups
- C08F290/14—Polymers provided for in subclass C08G
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
Abstract
Description
カラム:東ソー株式会社製ガードカラム「HXL-L」
+東ソー株式会社製「TSK-GEL G2000HXL」
+東ソー株式会社製「TSK-GEL G2000HXL」
+東ソー株式会社製「TSK-GEL G3000HXL」
+東ソー株式会社製「TSK-GEL G4000HXL」
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPC-8020モデルIIバージョン4.10」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPC-8020モデルIIバージョン4.10」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A-500」
東ソー株式会社製「A-1000」
東ソー株式会社製「A-2500」
東ソー株式会社製「A-5000」
東ソー株式会社製「F-1」
東ソー株式会社製「F-2」
東ソー株式会社製「F-4」
東ソー株式会社製「F-10」
東ソー株式会社製「F-20」
東ソー株式会社製「F-40」
東ソー株式会社製「F-80」
東ソー株式会社製「F-128」
試料 : 樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl) Measuring device: "HLC-8220 GPC" manufactured by Tosoh Corporation,
Column: Guard column "HXL-L" manufactured by Tosoh Corporation
+ "TSK-GEL G2000HXL" manufactured by Tosoh Corporation
+ "TSK-GEL G2000HXL" manufactured by Tosoh Corporation
+ "TSK-GEL G3000HXL" manufactured by Tosoh Corporation
+ "TSK-GEL G4000HXL" manufactured by Tosoh Corporation
Detector: RI (Differential Refractometer)
Data processing: "GPC-8020 Model II Version 4.10" manufactured by Tosoh Corporation
Measurement conditions: Column temperature 40°C
Developing solvent Tetrahydrofuran Flow rate 1.0 ml/min Standard: The following monodisperse polystyrene having a known molecular weight was used according to the measurement manual of "GPC-8020 Model II Version 4.10".
(Polystyrene used)
Tosoh Corporation "A-500"
Tosoh Corporation “A-1000”
Tosoh Corporation "A-2500"
"A-5000" manufactured by Tosoh Corporation
Tosoh Corporation "F-1"
Tosoh Corporation "F-2"
Tosoh Corporation "F-4"
Tosoh Corporation “F-10”
Tosoh Corporation “F-20”
Tosoh Corporation “F-40”
Tosoh Corporation “F-80”
Tosoh Corporation “F-128”
Sample: A solution obtained by filtering 1.0% by mass of a tetrahydrofuran solution in terms of resin solid content with a microfilter (50 μl).
温度計、撹拌機、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(DIC株式会社製「EPICLON 850-S」、エポキシ当量188g/当量。以下、「ビスフェノールA型エポキシ樹脂(1)」と略記する。)376質量部を仕込み、酸化防止剤としてジブチルヒドロキシトルエン0.22質量部、熱重合禁止剤としてメトキノン0.22質量部加えた後、アクリル酸72質量部、トリフェニルホスフィン0.22質量部を添加し、空気を吹き込みながら100℃で10時間エステル化反応を行った。次いで、酸価が1mgKOH/g以下であることを確認した後、シュウ酸0.22質量部を添加し、70℃で3時間撹拌して反応物(II-1)を得た。この反応物(II-1)のエポキシ当量は478g/当量であった。また、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基1モルに対する、アクリル酸が有する酸基のモル数は、0.5であった。 (Synthesis Example 1: Production of reaction product (II-1))
In a flask equipped with a thermometer, a stirrer, and a reflux condenser, a bisphenol A-type epoxy resin (“EPICLON 850-S” manufactured by DIC Corporation, epoxy equivalent 188 g/equivalent. Hereinafter, “bisphenol A-type epoxy resin (1)” 376 parts by mass are charged, and after adding 0.22 parts by mass of dibutylhydroxytoluene as an antioxidant and 0.22 parts by mass of metoquinone as a thermal polymerization inhibitor, 72 parts by mass of acrylic acid and 0 of triphenylphosphine are added. 0.22 parts by mass was added, and the esterification reaction was carried out at 100° C. for 10 hours while blowing air. Next, after confirming that the acid value was 1 mgKOH/g or less, 0.22 parts by mass of oxalic acid was added and stirred at 70° C. for 3 hours to obtain a reaction product (II-1). The epoxy equivalent of this reaction (II-1) was 478 g / equivalent. The number of moles of acid groups contained in acrylic acid was 0.5 with respect to 1 mole of epoxy groups contained in the bisphenol A type epoxy resin (2).
温度計、撹拌機、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(DIC株式会社製「EPICLON 850CRP」、エポキシ当量173g/当量。以下、「ビスフェノールA型エポキシ樹脂(2)」と略記する。)346質量部を仕込み、酸化防止剤としてジブチルヒドロキシトルエン0.21質量部、熱重合禁止剤としてメトキノン0.21質量部加えた後、アクリル酸72質量部、トリフェニルホスフィン0.21質量部を添加し、空気を吹き込みながら100℃で10時間エステル化反応を行った。次いで、酸価が1mgKOH/g以下であることを確認した後、シュウ酸0.21質量部を添加し、70℃で3時間撹拌して反応物(II-2)を得た。この反応物(II-2)のエポキシ当量は450g/当量であった。また、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基1モルに対する、アクリル酸が有する酸基のモル数は、0.5であった。 (Synthesis Example 2: Production of Reactant (II-2))
In a flask equipped with a thermometer, a stirrer, and a reflux condenser, a bisphenol A type epoxy resin (“EPICLON 850CRP” manufactured by DIC Corporation, an epoxy equivalent of 173 g/equivalent. Hereinafter, referred to as “bisphenol A type epoxy resin (2)”. After adding 346 parts by mass, 0.21 part by mass of dibutylhydroxytoluene as an antioxidant and 0.21 part by mass of methoquinone as a thermal polymerization inhibitor, 72 parts by mass of acrylic acid and 0.21 of triphenylphosphine are added. The mass part was added, and the esterification reaction was carried out at 100° C. for 10 hours while blowing air. Next, after confirming that the acid value was 1 mgKOH/g or less, 0.21 part by mass of oxalic acid was added and stirred at 70° C. for 3 hours to obtain a reaction product (II-2). The epoxy equivalent of this reaction (II-2) was 450 g / equivalent. The number of moles of acid groups contained in acrylic acid was 0.5 with respect to 1 mole of epoxy groups contained in the bisphenol A type epoxy resin (2).
温度計、撹拌機、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(2)346質量部を仕込み、酸化防止剤としてジブチルヒドロキシトルエン0.18質量部、熱重合禁止剤としてメトキノン0.18質量部加えた後、アクリル酸22質量部、トリフェニルホスフィン0.18質量部を添加し、空気を吹き込みながら100℃で5時間エステル化反応を行った。次いで、酸価が1mgKOH/g以下であることを確認した後、シュウ酸0.18質量部を添加し、70℃で3時間撹拌して反応物(II-3)を得た。この反応物(II-3)のエポキシ当量は241g/当量であった。また、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基1モルに対する、アクリル酸が有する酸基のモル数は、0.15であった。 (Synthesis Example 3: Production of Reactant (II-3))
A flask equipped with a thermometer, a stirrer, and a reflux condenser was charged with 346 parts by mass of bisphenol A type epoxy resin (2), 0.18 parts by mass of dibutylhydroxytoluene as an antioxidant, and methoquinone 0 as a thermal polymerization inhibitor. After adding 18 parts by mass, 22 parts by mass of acrylic acid and 0.18 parts by mass of triphenylphosphine were added, and the esterification reaction was carried out at 100° C. for 5 hours while blowing air. Next, after confirming that the acid value was 1 mgKOH/g or less, 0.18 parts by mass of oxalic acid was added and stirred at 70° C. for 3 hours to obtain a reaction product (II-3). The epoxy equivalent of this reaction (II-3) was 241 g / equivalent. In addition, the number of moles of acid groups contained in acrylic acid was 0.15 with respect to 1 mole of epoxy groups contained in the bisphenol A type epoxy resin (2).
温度計、撹拌機、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(2)346質量部を仕込み、酸化防止剤としてジブチルヒドロキシトルエン0.19質量部、熱重合禁止剤としてメトキノン0.19質量部加えた後、アクリル酸43質量部、トリフェニルホスフィン0.19質量部を添加し、空気を吹き込みながら100℃で8時間エステル化反応を行った。次いで、酸価が1mgKOH/g以下であることを確認した後、シュウ酸0.19質量部を添加し、70℃で3時間撹拌して反応物(II-4)を得た。この反応物(II-4)のエポキシ当量は301g/当量であった。また、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基1モルに対する、アクリル酸が有する酸基のモル数は、0.3であった。 (Synthesis Example 4: Production of Reactant (II-4))
A flask equipped with a thermometer, a stirrer, and a reflux condenser was charged with 346 parts by mass of bisphenol A type epoxy resin (2), 0.19 parts by mass of dibutylhydroxytoluene as an antioxidant, and methoquinone 0 as a thermal polymerization inhibitor. After adding 19 parts by mass, 43 parts by mass of acrylic acid and 0.19 parts by mass of triphenylphosphine were added, and the esterification reaction was carried out at 100° C. for 8 hours while blowing air. Next, after confirming that the acid value was 1 mgKOH/g or less, 0.19 parts by mass of oxalic acid was added, and the mixture was stirred at 70° C. for 3 hours to obtain a reaction product (II-4). The epoxy equivalent of this reaction (II-4) was 301 g / equivalent. The number of moles of acid groups contained in acrylic acid was 0.3 with respect to 1 mole of epoxy groups contained in the bisphenol A type epoxy resin (2).
温度計、撹拌機、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(2)346質量部を仕込み、酸化防止剤としてジブチルヒドロキシトルエン0.22質量部、熱重合禁止剤としてメトキノン0.22質量部加えた後、アクリル酸101質量部、トリフェニルホスフィン0.44質量部を添加し、空気を吹き込みながら100℃で10時間エステル化反応を行った。次いで、酸価が1mgKOH/g以下であることを確認した後、シュウ酸0.22質量部を添加し、70℃で3時間撹拌して反応物(II-5)を得た。この反応物(II-5)のエポキシ当量は785g/当量であった。また、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基1モルに対する、アクリル酸が有する酸基のモル数は、0.7であった。 (Synthesis Example 5: Production of Reactant (II-5))
A flask equipped with a thermometer, a stirrer, and a reflux condenser was charged with 346 parts by mass of bisphenol A type epoxy resin (2), 0.22 parts by mass of dibutylhydroxytoluene as an antioxidant, and methoquinone 0 as a thermal polymerization inhibitor. After adding 0.22 parts by mass, 101 parts by mass of acrylic acid and 0.44 parts by mass of triphenylphosphine were added, and an esterification reaction was carried out at 100° C. for 10 hours while blowing air. Next, after confirming that the acid value was 1 mgKOH/g or less, 0.22 parts by mass of oxalic acid was added and stirred at 70° C. for 3 hours to obtain a reaction product (II-5). The epoxy equivalent of this reaction (II-5) was 785 g / equivalent. The number of moles of acid groups contained in acrylic acid was 0.7 with respect to 1 mole of epoxy groups contained in the bisphenol A type epoxy resin (2).
温度計、撹拌機、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(2)346質量部を仕込み、酸化防止剤としてジブチルヒドロキシトルエン0.23質量部、熱重合禁止剤としてメトキノン0.23質量部加えた後、アクリル酸122質量部、トリフェニルホスフィン0.46質量部を添加し、空気を吹き込みながら100℃で20時間エステル化反応を行った。次いで、酸価が1mgKOH/g以下であることを確認した後、シュウ酸0.23質量部を添加し、70℃で3時間撹拌して反応物(II-6)を得た。この反応物(II-6)のエポキシ当量は1603g/当量であった。また、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基1モルに対する、アクリル酸が有する酸基のモル数は、0.85であった。 (Synthesis Example 6: Production of Reactant (II-6))
A flask equipped with a thermometer, a stirrer, and a reflux condenser was charged with 346 parts by mass of bisphenol A type epoxy resin (2), 0.23 parts by mass of dibutylhydroxytoluene as an antioxidant, and methoquinone 0 as a thermal polymerization inhibitor. After adding 0.23 parts by mass, 122 parts by mass of acrylic acid and 0.46 parts by mass of triphenylphosphine were added, and the esterification reaction was carried out at 100° C. for 20 hours while blowing air. Next, after confirming that the acid value was 1 mgKOH/g or less, 0.23 parts by mass of oxalic acid was added and stirred at 70° C. for 3 hours to obtain a reaction product (II-6). The epoxy equivalent of this reaction (II-6) was 1603 g / equivalent. In addition, the number of moles of the acid group of acrylic acid was 0.85 with respect to 1 mole of the epoxy group of the bisphenol A type epoxy resin (2).
温度計、撹拌機、及び還流冷却器を備えたフラスコに、ビスフェノールF型エポキシ樹脂(DIC株式会社製「EPICLON 830CRP」、エポキシ当量159g/当量。以下、「ビスフェノールF型エポキシ樹脂(1)」と略記する。)318質量部を仕込み、酸化防止剤としてジブチルヒドロキシトルエン0.2質量部、熱重合禁止剤としてメトキノン0.2質量部加えた後、アクリル酸72質量部、トリフェニルホスフィン0.2質量部を添加し、空気を吹き込みながら100℃で10時間エステル化反応を行った。次いで、酸価が1mgKOH/g以下であることを確認した後、シュウ酸0.2質量部を添加し、70℃で3時間撹拌して反応物(II-7)を得た。この反応物(II-7)のエポキシ当量は421g/当量であった。また、ビスフェノールF型エポキシ樹脂(1)が有するエポキシ基1モルに対する、アクリル酸が有する酸基のモル数は、0.5であった。 (Synthesis Example 7: Production of Reactant (II-7))
In a flask equipped with a thermometer, a stirrer, and a reflux condenser, a bisphenol F type epoxy resin (“EPICLON 830CRP” manufactured by DIC Corporation, epoxy equivalent 159 g/equivalent. Hereinafter, referred to as “bisphenol F type epoxy resin (1)”. 318 parts by mass are charged, and 0.2 parts by mass of dibutylhydroxytoluene as an antioxidant and 0.2 parts by mass of metoquinone as a thermal polymerization inhibitor are added, and then 72 parts by mass of acrylic acid and 0.2 parts of triphenylphosphine. The mass part was added, and the esterification reaction was carried out at 100° C. for 10 hours while blowing air. Next, after confirming that the acid value was 1 mgKOH/g or less, 0.2 part by mass of oxalic acid was added and stirred at 70° C. for 3 hours to obtain a reaction product (II-7). The epoxy equivalent of this reaction (II-7) was 421 g / equivalent. The number of moles of the acid group of acrylic acid was 0.5 with respect to 1 mole of the epoxy group of the bisphenol F type epoxy resin (1).
温度計、撹拌機、及び還流冷却器を備えたフラスコに、ナフタレン型エポキシ樹脂(DIC株式会社製「EPICLON 4032D」、エポキシ当量141g/当量。以下、「ナフタレン型エポキシ樹脂(1)」と略記する。)282質量部を仕込み、酸化防止剤としてジブチルヒドロキシトルエン0.18質量部、熱重合禁止剤としてメトキノン0.18質量部加えた後、アクリル酸72質量部、トリフェニルホスフィン0.18質量部を添加し、空気を吹き込みながら100℃で10時間エステル化反応を行った。次いで、酸価が1mgKOH/g以下であることを確認した後、シュウ酸0.18質量部を添加し、70℃で3時間撹拌して反応物(II-8)を得た。この反応物(II-8)のエポキシ当量は388g/当量であった。また、ナフタレン型エポキシ樹脂(1)が有するエポキシ基1モルに対する、アクリル酸が有する酸基のモル数は、0.5であった。 (Synthesis Example 8: Production of Reactant (II-8))
In a flask equipped with a thermometer, a stirrer, and a reflux condenser, a naphthalene type epoxy resin (“EPICLON 4032D” manufactured by DIC Corporation, an epoxy equivalent of 141 g/equivalent. Hereinafter, abbreviated as “naphthalene type epoxy resin (1)”. 282 parts by mass are added, 0.18 parts by mass of dibutylhydroxytoluene as an antioxidant and 0.18 parts by mass of methquinone as a thermal polymerization inhibitor are added, and then 72 parts by mass of acrylic acid and 0.18 parts by mass of triphenylphosphine. Was added, and the esterification reaction was carried out at 100 ° C. for 10 hours while blowing air. Next, after confirming that the acid value was 1 mgKOH/g or less, 0.18 parts by mass of oxalic acid was added and stirred at 70° C. for 3 hours to obtain a reaction product (II-8). The epoxy equivalent of this reaction (II-8) was 388 g / equivalent. The number of moles of acid groups contained in acrylic acid was 0.5 with respect to 1 mole of epoxy groups contained in the naphthalene-type epoxy resin (1).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ジエチレングリコールモノメチルエーテルアセテート101質量部を入れ、オルソクレゾールノボラック型エポキシ樹脂(DIC株式会社製「EPICLON N-680」、エポキシ当量:214g/当量)428質量部を溶解し、ジブチルヒドロキシトルエン4質量部、メトキノン0.4質量部加えた後、アクリル酸144質量部、トリフェニルホスフィン1.6質量部を添加し、空気を吹き込みながら120℃で10時間エステル化反応を行なった。その後、ジエチレングリコールモノメチルエーテルアセテート311質量部、テトラヒドロ無水フタル酸160質量部を加え110℃で2.5時間反応し、目的の酸基含有アクリレート樹脂(P)を得た。この酸基含有アクリレート樹脂(P)の固形分酸価は85mgKOH/gであり、重量平均分子量は、8540であった。 (Synthesis Example 9: Production of Acid Group-Containing Acrylate Resin (P))
101 parts by mass of diethylene glycol monomethyl ether acetate was placed in a flask equipped with a thermometer, a stirrer, and a reflux condenser, and an orthocresol novolac type epoxy resin (“EPICLON N-680” manufactured by DIC Corporation, epoxy equivalent: 214 g/equivalent). ) 428 parts by mass were dissolved, 4 parts by mass of dibutylhydroxytoluene and 0.4 parts by mass of methquinone were added, then 144 parts by mass of acrylic acid and 1.6 parts by mass of triphenylphosphine were added, and at 120° C. while blowing air. The esterification reaction was carried out for 10 hours. Then, 311 parts by mass of diethylene glycol monomethyl ether acetate and 160 parts by mass of tetrahydrophthalic anhydride were added and reacted at 110° C. for 2.5 hours to obtain a target acid group-containing acrylate resin (P). The acid value of the solid content of this acid group-containing acrylate resin (P) was 85 mgKOH/g, and the weight average molecular weight was 8540.
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート162質量部を添加し、110℃で3時間反応させ反応物(I-1)を得た。次いでビスフェノールA型エポキシ樹脂(2)97質量部を添加し、110℃で2時間反応させた後、アクリル酸20質量部を添加し、120℃で3時間反応させて、目的の酸基含有アクリレート樹脂(1)を得た。この酸基含有アクリレート樹脂(1)の固形分酸価は89mgKOH/gであり、重量平均分子量は、5670であった。また、反応物(I-1)が有する酸基1モルに対する、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基のモル数は、0.56であった。 (Example 1: Production of acid group-containing acrylate resin (1))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Then, 100 parts by mass of succinic anhydride and 162 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-1). Next, 97 parts by mass of the bisphenol A type epoxy resin (2) was added and reacted at 110 ° C. for 2 hours, then 20 parts by mass of acrylic acid was added and reacted at 120 ° C. for 3 hours to obtain the desired acid group-containing acrylate. Resin (1) was obtained. The acid value of the solid content of the acid group-containing acrylate resin (1) was 89 mgKOH/g, and the weight average molecular weight was 5,670. The number of moles of the epoxy group of the bisphenol A type epoxy resin (2) was 0.56, relative to 1 mole of the acid group of the reaction product (I-1).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート200質量部を添加し、110℃で3時間反応させ反応物(I-2)を得た。次いでビスフェノールA型エポキシ樹脂(2)138質量部を添加し、110℃で2時間反応させた後、アクリル酸28質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(2)を得た。この酸基含有アクリレート樹脂(2)の固形分酸価は69mgKOH/gであり、重量平均分子量は、6070であった。また、反応物(I-2)が有する酸基1モルに対する、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基のモル数は、0.80であった。 (Example 2: Production of acid group-containing acrylate resin (2))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Next, 100 parts by mass of succinic anhydride and 200 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-2). Next, 138 parts by mass of the bisphenol A type epoxy resin (2) was added and reacted at 110 ° C. for 2 hours, then 28 parts by mass of acrylic acid was added and reacted at 120 ° C. for 5 hours to obtain the desired acid group-containing acrylate. The resin (2) was obtained. The solid acid value of the acid group-containing acrylate resin (2) was 69 mgKOH / g, and the weight average molecular weight was 6070. The number of moles of the epoxy group of the bisphenol A type epoxy resin (2) was 0.80, relative to 1 mole of the acid group of the reaction product (I-2).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート122質量部を添加し、110℃で3時間反応させ反応物(I-3)を得た。次いでビスフェノールA型エポキシ樹脂(2)49質量部を添加し、110℃で2時間反応させた後、アクリル酸10質量部を添加し、120℃で3時間反応させて、目的の酸基含有アクリレート樹脂(3)を得た。この酸基含有アクリレート樹脂(3)の固形分酸価は115mgKOH/gであり、重量平均分子量は、5180であった。また、反応物(I-3)が有する酸基1モルに対する、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基のモル数は、0.28であった。 (Example 3: Production of acid group-containing acrylate resin (3))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at 0°C for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. Was reacted for 6 hours. Next, 100 parts by mass of succinic anhydride and 122 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-3). Next, 49 parts by mass of the bisphenol A type epoxy resin (2) was added and reacted at 110 ° C. for 2 hours, then 10 parts by mass of acrylic acid was added and reacted at 120 ° C. for 3 hours to obtain the desired acid group-containing acrylate. Resin (3) was obtained. The solid acid value of the acid group-containing acrylate resin (3) was 115 mgKOH / g, and the weight average molecular weight was 5180. The number of moles of the epoxy group of the bisphenol A type epoxy resin (2) was 0.28, relative to 1 mole of the acid group of the reaction product (I-3).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート223質量部を添加し、110℃で3時間反応させ反応物(I-4)を得た。次いでビスフェノールA型エポキシ樹脂(2)153質量部を添加し、110℃で2時間反応させた後、アクリル酸31質量部を添加し、120℃で6時間反応させて、目的の酸基含有アクリレート樹脂(4)を得た。この酸基含有アクリレート樹脂(4)の固形分酸価は63mgKOH/gであり、重量平均分子量は、6410であった。また、反応物(I-4)が有する酸基1モルに対する、ビスフェノールA型エポキシ樹脂(2)が有するエポキシ基のモル数は、0.89であった。 (Example 4: Production of acid group-containing acrylate resin (4))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at 0°C for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Next, 100 parts by mass of succinic anhydride and 223 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-4). Next, 153 parts by mass of bisphenol A type epoxy resin (2) was added and reacted at 110 ° C. for 2 hours, then 31 parts by mass of acrylic acid was added and reacted at 120 ° C. for 6 hours to obtain the desired acid group-containing acrylate. Resin (4) was obtained. The acid value of the solid content of the acid group-containing acrylate resin (4) was 63 mgKOH/g, and the weight average molecular weight was 6410. The number of moles of the epoxy group of the bisphenol A type epoxy resin (2) was 0.89, relative to 1 mole of the acid group of the reaction product (I-4).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート177質量部を添加し、110℃で3時間反応させ反応物(I-5)を得た。次いで、合成例1で得た反応物(II-1)124質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(5)を得た。この酸基含有アクリレート樹脂(5)の固形分酸価は87mgKOH/gであり、重量平均分子量は、5090であった。また、反応物(I-5)が有する酸基1モルに対する、反応物(II-1)が有するエポキシ基のモル数は、0.26であった。 (Example 5: Production of acid group-containing acrylate resin (5))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at 0°C for 2 hours. Next, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of methquinone, 46 parts by mass of acrylic acid, and 1.4 parts by mass of triphenylphosphine were added, and the temperature was 120 ° C. while blowing air. Was reacted for 6 hours. Then, 100 parts by mass of succinic anhydride and 177 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-5). Next, 124 parts by mass of the reaction product (II-1) obtained in Synthesis Example 1 was added and reacted at 120° C. for 5 hours to obtain the target acid group-containing acrylate resin (5). The solid acid value of the acid group-containing acrylate resin (5) was 87 mgKOH / g, and the weight average molecular weight was 5090. The number of moles of the epoxy group contained in the reaction product (II-1) was 0.26 with respect to 1 mol of the acid group contained in the reaction product (I-5).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート162質量部を添加し、110℃で3時間反応させ反応物(I-6)を得た。次いで、合成例2で得た反応物(II-2)117質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(6)を得た。この酸基含有アクリレート樹脂(6)の固形分酸価は87mgKOH/gであり、重量平均分子量は、4920であった。また、反応物(I-6)が有する酸基1モルに対する、反応物(II-2)が有するエポキシ基のモル数は、0.26であった。 (Example 6: Production of acid group-containing acrylate resin (6))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at 0°C for 2 hours. Next, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of methquinone, 46 parts by mass of acrylic acid, and 1.4 parts by mass of triphenylphosphine were added, and the temperature was 120 ° C. while blowing air. And reacted for 6 hours. Then, 100 parts by mass of succinic anhydride and 162 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-6). Then, 117 parts by mass of the reaction product (II-2) obtained in Synthesis Example 2 was added and reacted at 120° C. for 5 hours to obtain the target acid group-containing acrylate resin (6). The acid value of the solid content of this acid group-containing acrylate resin (6) was 87 mgKOH/g, and the weight average molecular weight was 4920. The number of moles of the epoxy group of the reactant (II-2) was 0.26 with respect to 1 mole of the acid group of the reactant (I-6).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート200質量部を添加し、110℃で3時間反応させ反応物(I-7)を得た。次いで、合成例2で得た反応物(II-2)167質量部を添加し、120℃で7時間反応させて、目的の酸基含有アクリレート樹脂(7)を得た。この酸基含有アクリレート樹脂(7)の固形分酸価は68mgKOH/gであり、重量平均分子量は、5880であった。また、反応物(I-7)が有する酸基1モルに対する、反応物(II-2)が有するエポキシ基のモル数は、0.37であった。 (Example 7: Production of acid group-containing acrylate resin (7))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. Was reacted for 6 hours. Next, 100 parts by mass of succinic anhydride and 200 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-7). Then, 167 parts by mass of the reaction product (II-2) obtained in Synthesis Example 2 was added and reacted at 120° C. for 7 hours to obtain a target acid group-containing acrylate resin (7). The solid acid value of the acid group-containing acrylate resin (7) was 68 mgKOH / g, and the weight average molecular weight was 5880. The number of moles of the epoxy group of the reactant (II-2) was 0.37 with respect to 1 mole of the acid group of the reactant (I-7).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート122質量部を添加し、110℃で3時間反応させ反応物(I-8)を得た。次いで、合成例2で得た反応物(II-2)59質量部を添加し、120℃で3時間反応させて、目的の酸基含有アクリレート樹脂(8)を得た。この酸基含有アクリレート樹脂(8)の固形分酸価は116mgKOH/gであり、重量平均分子量は、5020であった。また、反応物(I-8)が有する酸基1モルに対する、反応物(II-2)が有するエポキシ基のモル数は、0.13であった。 (Example 8: Production of acid group-containing acrylate resin (8))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Then, 100 parts by mass of succinic anhydride and 122 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-8). Next, 59 parts by mass of the reaction product (II-2) obtained in Synthesis Example 2 was added and reacted at 120° C. for 3 hours to obtain the target acid group-containing acrylate resin (8). The acid value of the solid content of the acid group-containing acrylate resin (8) was 116 mgKOH/g, and the weight average molecular weight was 5020. The number of moles of the epoxy group of the reactant (II-2) was 0.13 with respect to 1 mole of the acid group of the reactant (I-8).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート223質量部を添加し、110℃で3時間反応させ反応物(I-9)を得た。次いで、合成例2で得た反応物(II-2)185質量部を添加し、120℃で6時間反応させて、目的の酸基含有アクリレート樹脂(9)を得た。この酸基含有アクリレート樹脂(9)の固形分酸価は63mgKOH/gであり、重量平均分子量は、6290であった。また、反応物(I-9)が有する酸基1モルに対する、反応物(II-2)が有するエポキシ基のモル数は、0.41であった。 (Example 9: Production of acid group-containing acrylate resin (9))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at 0°C for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. Was reacted for 6 hours. Next, 100 parts by mass of succinic anhydride and 223 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-9). Then, 185 parts by mass of the reaction product (II-2) obtained in Synthesis Example 2 was added and reacted at 120° C. for 6 hours to obtain the target acid group-containing acrylate resin (9). The acid value of the solid content of the acid group-containing acrylate resin (9) was 63 mgKOH/g, and the weight average molecular weight was 6,290. The number of moles of the epoxy group of the reactant (II-2) was 0.41 with respect to 1 mole of the acid group of the reactant (I-9).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート165質量部を添加し、110℃で3時間反応させ反応物(I-10)を得た。次いで、合成例3で得た反応物(II-3)63質量部を添加し、120℃で6時間反応させて、目的の酸基含有アクリレート樹脂(10)を得た。この酸基含有アクリレート樹脂(10)の固形分酸価は98mgKOH/gであり、重量平均分子量は、6030であった。また、反応物(I-10)が有する酸基1モルに対する、反応物(II-3)が有するエポキシ基のモル数は、0.26であった。 (Example 10: Production of acid group-containing acrylate resin (10))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Then, 100 parts by mass of succinic anhydride and 165 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-10). Then, 63 parts by mass of the reaction product (II-3) obtained in Synthesis Example 3 was added and reacted at 120° C. for 6 hours to obtain a target acid group-containing acrylate resin (10). The acid value of the solid content of this acid group-containing acrylate resin (10) was 98 mgKOH/g, and the weight average molecular weight was 6030. The number of moles of the epoxy group of the reactant (II-3) was 0.26 with respect to 1 mole of the acid group of the reactant (I-10).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート175質量部を添加し、110℃で3時間反応させ反応物(I-11)を得た。次いで、合成例4で得た反応物(II-4)78質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(11)を得た。この酸基含有アクリレート樹脂(11)の固形分酸価は95mgKOH/gであり、重量平均分子量は、5890であった。また、反応物(I-11)が有する酸基1モルに対する、反応物(II-4)が有するエポキシ基のモル数は、0.26であった。 (Example 11: Production of acid group-containing acrylate resin (11))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. Was reacted for 6 hours. Next, 100 parts by mass of succinic anhydride and 175 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-11). Then, 78 parts by mass of the reaction product (II-4) obtained in Synthesis Example 4 was added and reacted at 120° C. for 5 hours to obtain a target acid group-containing acrylate resin (11). The solid acid value of the acid group-containing acrylate resin (11) was 95 mgKOH / g, and the weight average molecular weight was 5890. The number of moles of the epoxy group of the reaction product (II-4) was 0.26 with respect to 1 mole of the acid group of the reaction product (I-11).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート249質量部を添加し、110℃で3時間反応させ反応物(I-12)を得た。次いで、合成例5で得た反応物(II-5)204質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(12)を得た。この酸基含有アクリレート樹脂(12)の固形分酸価は75mgKOH/gであり、重量平均分子量は、5310であった。また、反応物(I-12)が有する酸基1モルに対する、反応物(II-5)が有するエポキシ基のモル数は、0.26であった。 (Example 12: Production of acid group-containing acrylate resin (12))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. Was reacted for 6 hours. Next, 100 parts by mass of succinic anhydride and 249 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-12). Then, 204 parts by mass of the reaction product (II-5) obtained in Synthesis Example 5 was added and reacted at 120° C. for 5 hours to obtain a target acid group-containing acrylate resin (12). The solid acid value of the acid group-containing acrylate resin (12) was 75 mgKOH / g, and the weight average molecular weight was 5310. The number of moles of the epoxy group contained in the reaction product (II-5) was 0.26 with respect to 1 mol of the acid group contained in the reaction product (I-12).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート298質量部を添加し、110℃で3時間反応させ反応物(I-13)を得た。次いで、合成例6で得た反応物(II-6)289質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(13)を得た。この酸基含有アクリレート樹脂(13)の固形分酸価は73mgKOH/gであり、重量平均分子量は、5060であった。また、反応物(I-13)が有する酸基1モルに対する、反応物(II-6)が有するエポキシ基のモル数は、0.18であった。 (Example 13: Production of acid group-containing acrylate resin (13))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Then, 100 parts by mass of succinic anhydride and 298 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-13). Then, 289 parts by mass of the reaction product (II-6) obtained in Synthesis Example 6 was added and reacted at 120° C. for 5 hours to obtain a target acid group-containing acrylate resin (13). The solid acid value of the acid group-containing acrylate resin (13) was 73 mgKOH / g, and the weight average molecular weight was 5060. The number of moles of the epoxy group contained in the reaction product (II-6) was 0.18, relative to 1 mol of the acid group contained in the reaction product (I-13).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールF型エポキシ樹脂(DIC株式会社製「EPICLON 830-S」、エポキシ当量169g/当量。以下、「ビスフェノールF型エポキシ樹脂(2)」と略記する。)169質量部、ビスフェノールF42質量部、トリフェニルホスフィン0.4質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート84質量部、ジブチルヒドロキシトルエン0.5質量部、メトキノン0.2質量部、アクリル酸42質量部、トリフェニルホスフィン1.3質量部を添加し、空気を吹き込みながら120℃で7時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート154質量部を添加し、110℃で3時間反応させ反応物(I-14)を得た。次いで、合成例7で得た反応物(II-7)110質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(14)を得た。この酸基含有アクリレート樹脂(14)の固形分酸価は94mgKOH/gであり、重量平均分子量は、4880であった。また、反応物(I-14)が有する酸基1モルに対する、反応物(II-7)が有するエポキシ基のモル数は、0.26であった。 (Example 14: Production of acid group-containing acrylate resin (14))
In a flask equipped with a thermometer, a stirrer, and a reflux condenser, a bisphenol F type epoxy resin (“EPICLON 830-S” manufactured by DIC Corporation, epoxy equivalent 169 g/equivalent. Hereinafter, “bisphenol F type epoxy resin (2)” 169 parts by mass, bisphenol F 42 parts by mass, and triphenylphosphine 0.4 parts by mass were added and reacted at 140° C. for 2 hours in a nitrogen atmosphere. Then, 84 parts by mass of diethylene glycol monomethyl ether acetate, 0.5 parts by mass of dibutylhydroxytoluene, 0.2 parts by mass of metoquinone, 42 parts by mass of acrylic acid, 1.3 parts by mass of triphenylphosphine are added, and 120°C while blowing air. And reacted for 7 hours. Next, 100 parts by mass of succinic anhydride and 154 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-14). Then, 110 parts by mass of the reaction product (II-7) obtained in Synthesis Example 7 was added and reacted at 120° C. for 5 hours to obtain a target acid group-containing acrylate resin (14). The acid value of the solid content of this acid group-containing acrylate resin (14) was 94 mgKOH/g, and the weight average molecular weight was 4,880. The number of moles of the epoxy group contained in the reaction product (II-7) was 0.26, relative to 1 mol of the acid group contained in the reaction product (I-14).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート161質量部を添加し、110℃で3時間反応させ反応物(I-15)を得た。次いで、合成例7で得た反応物(II-7)115質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(15)を得た。この酸基含有アクリレート樹脂(15)の固形分酸価は86mgKOH/gであり、重量平均分子量は、4890であった。また、反応物(I-15)が有する酸基1モルに対する、反応物(II-7)が有するエポキシ基のモル数は、0.26であった。 (Example 15: Production of acid group-containing acrylate resin (15))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Then, 100 parts by mass of succinic anhydride and 161 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-15). Next, 115 parts by mass of the reaction product (II-7) obtained in Synthesis Example 7 was added and reacted at 120° C. for 5 hours to obtain the target acid group-containing acrylate resin (15). The acid value of the solid content of the acid group-containing acrylate resin (15) was 86 mgKOH/g, and the weight average molecular weight was 4,890. The number of moles of the epoxy group contained in the reaction product (II-7) was 0.26 with respect to 1 mol of the acid group contained in the reaction product (I-15).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、テトラヒドロ無水フタル酸152質量部、ジエチレングリコールモノメチルエーテルアセテート197質量部を添加し、110℃で4時間反応させ反応物(I-16)を得た。次いで、合成例2で得た反応物(II-2)108質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(16)を得た。この酸基含有アクリレート樹脂(16)の固形分酸価は83mgKOH/gであり、重量平均分子量は、5010であった。また、反応物(I-16)が有する酸基1モルに対する、反応物(II-2)が有するエポキシ基のモル数は、0.24であった。 (Example 16: Production of acid group-containing acrylate resin (16))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at 0°C for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. Was reacted for 6 hours. Next, 152 parts by mass of tetrahydrophthalic anhydride and 197 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 4 hours to obtain a reaction product (I-16). Then, 108 parts by mass of the reaction product (II-2) obtained in Synthesis Example 2 was added and reacted at 120° C. for 5 hours to obtain a target acid group-containing acrylate resin (16). The solid acid value of the acid group-containing acrylate resin (16) was 83 mgKOH / g, and the weight average molecular weight was 5010. The number of moles of the epoxy group contained in the reaction product (II-2) was 0.24, relative to 1 mol of the acid group contained in the reaction product (I-16).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールF型エポキシ樹脂(2)169質量部、ビスフェノールF42質量部、トリフェニルホスフィン0.4質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート84質量部、ジブチルヒドロキシトルエン0.5質量部、メトキノン0.2質量部、アクリル酸42質量部、トリフェニルホスフィン1.3質量部を添加し、空気を吹き込みながら120℃で7時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート158質量部を添加し、110℃で3時間反応させ反応物(I-17)を得た。次いで、合成例2で得た反応物(II-2)117質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(17)を得た。この酸基含有アクリレート樹脂(17)の固形分酸価は92mgKOH/gであり、重量平均分子量は、49000であった。また、反応物(I-17)が有する酸基1モルに対する、反応物(II-2)が有するエポキシ基のモル数は、0.26であった。 (Example 17: Production of acid group-containing acrylate resin (17))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 169 parts by mass of the bisphenol F type epoxy resin (2), 42 parts by mass of bisphenol F, and 0.4 parts by mass of triphenylphosphine were added, and the mixture was placed under a nitrogen atmosphere at 140 The reaction was carried out at 0°C for 2 hours. Next, 84 parts by mass of diethylene glycol monomethyl ether acetate, 0.5 parts by mass of dibutylhydroxytoluene, 0.2 parts by mass of methquinone, 42 parts by mass of acrylic acid, and 1.3 parts by mass of triphenylphosphine were added, and 120 ° C. was blown with air. Was reacted for 7 hours. Then, 100 parts by mass of succinic anhydride and 158 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-17). Then, 117 parts by mass of the reaction product (II-2) obtained in Synthesis Example 2 was added and reacted at 120° C. for 5 hours to obtain a target acid group-containing acrylate resin (17). The acid value of the solid content of the acid group-containing acrylate resin (17) was 92 mgKOH/g, and the weight average molecular weight was 49000. The number of moles of the epoxy group of the reaction product (II-2) was 0.26 with respect to 1 mole of the acid group of the reaction product (I-17).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ナフタレン型エポキシ樹脂(1)141質量部、2,7-ジヒドロキシナフタレン35質量部、トリフェニルホスフィン0.4質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート72質量部、ジブチルヒドロキシトルエン0.4質量部、メトキノン0.2質量部、アクリル酸40質量部、トリフェニルホスフィン1.1質量部を添加し、空気を吹き込みながら120℃で7時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート161質量部を添加し、110℃で3時間反応させ反応物(I-18)を得た。次いで、合成例8で得た反応物(II-8)116質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(18)を得た。この酸基含有アクリレート樹脂(18)の固形分酸価は94mgKOH/gであり、重量平均分子量は、4750であった。また、反応物(I-18)が有する酸基1モルに対する、反応物(II-8)が有するエポキシ基のモル数は、0.3であった。 (Example 18: Production of acid group-containing acrylate resin (18))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 141 parts by mass of naphthalene-type epoxy resin (1), 35 parts by mass of 2,7-dihydroxynaphthalene, and 0.4 parts by mass of triphenylphosphine were added, and nitrogen was added. The reaction was carried out at 140° C. for 2 hours in the atmosphere. Next, 72 parts by mass of diethylene glycol monomethyl ether acetate, 0.4 parts by mass of dibutylhydroxytoluene, 0.2 parts by mass of methoquinone, 40 parts by mass of acrylic acid and 1.1 parts by mass of triphenylphosphine were added, and 120°C while blowing air. Was reacted for 7 hours. Then, 100 parts by mass of succinic anhydride and 161 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-18). Then, 116 parts by mass of the reaction product (II-8) obtained in Synthesis Example 8 was added and reacted at 120° C. for 5 hours to obtain the target acid group-containing acrylate resin (18). The solid acid value of the acid group-containing acrylate resin (18) was 94 mgKOH / g, and the weight average molecular weight was 4750. The number of moles of the epoxy group of the reactant (II-8) was 0.3 with respect to 1 mole of the acid group of the reactant (I-18).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート165質量部を添加し、110℃で3時間反応させ反応物(I-19)を得た。次いで、合成例8で得た反応物(II-8)101質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(19)を得た。この酸基含有アクリレート樹脂(19)の固形分酸価は90mgKOH/gであり、重量平均分子量は、4870であった。また、反応物(I-19)が有する酸基1モルに対する、反応物(II-8)が有するエポキシ基のモル数は、0.26であった。 (Example 19: Production of acid group-containing acrylate resin (19))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Then, 100 parts by mass of succinic anhydride and 165 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-19). Next, 101 parts by mass of the reaction product (II-8) obtained in Synthesis Example 8 was added and reacted at 120° C. for 5 hours to obtain the target acid group-containing acrylate resin (19). The solid acid value of the acid group-containing acrylate resin (19) was 90 mgKOH / g, and the weight average molecular weight was 4870. The number of moles of the epoxy group contained in the reaction product (II-8) was 0.26 with respect to 1 mol of the acid group contained in the reaction product (I-19).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート77質量部を添加し、110℃で3時間反応させ反応物(I-20)を得た。次いで、合成例2で得た反応物(II-2)18質量部を添加し、120℃で3時間反応させて、目的の酸基含有アクリレート樹脂(20)を得た。この酸基含有アクリレート樹脂(20)の固形分酸価は140mgKOH/gであり、重量平均分子量は、4760であった。また、反応物(I-20)が有する酸基1モルに対する、反応物(II-2)が有するエポキシ基のモル数は、0.04であった。 (Example 20: Production of acid group-containing acrylate resin (20))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Next, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of methquinone, 46 parts by mass of acrylic acid, and 1.4 parts by mass of triphenylphosphine were added, and the temperature was 120 ° C. while blowing air. Was reacted for 6 hours. Next, 100 parts by mass of succinic anhydride and 77 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-20). Then, 18 parts by mass of the reaction product (II-2) obtained in Synthesis Example 2 was added and reacted at 120° C. for 3 hours to obtain a target acid group-containing acrylate resin (20). The acid value of the solid content of this acid group-containing acrylate resin (20) was 140 mgKOH/g, and the weight average molecular weight was 4760. The number of moles of the epoxy group contained in the reaction product (II-2) was 0.04 with respect to 1 mol of the acid group contained in the reaction product (I-20).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、アクリル酸46質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート77質量部を添加し、110℃で3時間反応させ反応物(I-21)を得た。次いで、合成例2で得た反応物(II-2)23質量部、ビスフェノールA型エポキシ樹脂(2)35質量部を添加し、120℃で5時間反応させて、目的の酸基含有アクリレート樹脂(21)を得た。この酸基含有アクリレート樹脂(20)の固形分酸価は100mgKOH/gであり、重量平均分子量は、8200であった。また、反応物(I-21)が有する酸基1モルに対する、反応物(II-2)が有するエポキシ基のモル数は、0.05であった。 (Example 21: Production of acid group-containing acrylate resin (21))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Then, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 46 parts by mass of acrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Then, 100 parts by mass of succinic anhydride and 77 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-21). Next, 23 parts by mass of the reaction product (II-2) obtained in Synthesis Example 2 and 35 parts by mass of the bisphenol A type epoxy resin (2) were added and reacted at 120 ° C. for 5 hours to obtain the desired acid group-containing acrylate resin. (21) was obtained. The acid value of the solid content of the acid group-containing acrylate resin (20) was 100 mgKOH/g, and the weight average molecular weight was 8200. The number of moles of the epoxy group of the reaction product (II-2) was 0.05 with respect to 1 mole of the acid group of the reaction product (I-21).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ビスフェノールA41質量部、トリフェニルホスフィン0.5質量部を添加し、窒素雰囲気下、140℃で2時間反応させた。次いで、ジエチレングリコールモノメチルエーテルアセテート92質量部、ジブチルヒドロキシトルエン0.6質量部、メトキノン0.3質量部、メタクリル酸55質量部、トリフェニルホスフィン1.4質量部を添加し、空気を吹き込みながら120℃で6時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート162質量部を添加し、110℃で3時間反応させ反応物(I-22)を得た。次いで、合成例2で得た反応物(II-2)117質量部を添加し、120℃で5時間反応させて、目的の酸基含有メタクリレート樹脂(1)を得た。この酸基含有メタクリレート樹脂(1)の固形分酸価は86mgKOH/gであり、重量平均分子量は、4840であった。また、反応物(I-22)が有する酸基1モルに対する、反応物(II-2)が有するエポキシ基のモル数は、0.26であった。 (Example 22: Production of acid group-containing methacrylate resin (1))
To a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 41 parts by mass of bisphenol A, and 0.5 parts by mass of triphenylphosphine were added, and the mixture was heated under a nitrogen atmosphere to 140 The reaction was carried out at ° C. for 2 hours. Next, 92 parts by mass of diethylene glycol monomethyl ether acetate, 0.6 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of metoquinone, 55 parts by mass of methacrylic acid, 1.4 parts by mass of triphenylphosphine were added, and 120°C while blowing air. And reacted for 6 hours. Next, 100 parts by mass of succinic anhydride and 162 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours to obtain a reaction product (I-22). Then, 117 parts by mass of the reaction product (II-2) obtained in Synthesis Example 2 was added and reacted at 120° C. for 5 hours to obtain a target acid group-containing methacrylate resin (1). The solid acid value of the acid group-containing methacrylate resin (1) was 86 mgKOH / g, and the weight average molecular weight was 4840. The number of moles of the epoxy group of the reactant (II-2) was 0.26 with respect to 1 mole of the acid group of the reactant (I-22).
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ジエチレングリコールモノメチルエーテルアセテート87質量部、ジブチルヒドロキシトルエン0.5質量部、メトキノン0.3質量部、アクリル酸72質量部、トリフェニルホスフィン1.3質量部を添加し、空気を吹き込みながら120℃で8時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート241質量部を添加し、110℃で3時間反応させた。次いで、ビスフェノールA型エポキシ樹脂(1)150質量部を添加し、120℃で8時間反応させた。次いで、無水コハク酸72質量部を添加し、110℃で3時間反応させ、目的の酸基含有アクリレート樹脂(C1)を得た。この酸基含有アクリレート樹脂(C1)の固形分酸価は91mgKOH/gであった。 (Comparative Example 1: Production of Acid Group-Containing Acrylate Resin (C1))
In a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 87 parts by mass of diethylene glycol monomethyl ether acetate, 0.5 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of methquinone. Parts, 72 parts by mass of acrylic acid and 1.3 parts by mass of triphenylphosphine were added, and the mixture was reacted at 120 ° C. for 8 hours while blowing air. Then, 100 parts by mass of succinic anhydride and 241 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours. Next, 150 parts by mass of bisphenol A type epoxy resin (1) was added and reacted at 120° C. for 8 hours. Next, 72 parts by mass of succinic anhydride was added and reacted at 110 ° C. for 3 hours to obtain the desired acid group-containing acrylate resin (C1). The acid value of the solid content of the acid group-containing acrylate resin (C1) was 91 mgKOH/g.
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ジエチレングリコールモノメチルエーテルアセテート87質量部、ジブチルヒドロキシトルエン0.5質量部、メトキノン0.3質量部、アクリル酸72質量部、トリフェニルホスフィン1.3質量部を添加し、空気を吹き込みながら120℃で8時間反応させた。次いで、無水コハク酸100質量部、ジエチレングリコールモノメチルエーテルアセテート232質量部を添加し、110℃で3時間反応させた。次いで、ビスフェノールF型エポキシ樹脂(2)135質量部を添加し、120℃で8時間反応させた。次いで、無水コハク酸72質量部を添加し、110℃で3時間反応させ、目的の酸基含有アクリレート樹脂(C2)を得た。この酸基含有アクリレート樹脂(C2)の固形分酸価は94mgKOH/gであった。 (Comparative Example 2: Production of Acid Group-Containing Acrylate Resin (C2))
In a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 87 parts by mass of diethylene glycol monomethyl ether acetate, 0.5 parts by mass of dibutylhydroxytoluene, 0.3 parts by mass of methquinone. Parts, 72 parts by mass of acrylic acid and 1.3 parts by mass of triphenylphosphine were added, and the mixture was reacted at 120 ° C. for 8 hours while blowing air. Then, 100 parts by mass of succinic anhydride and 232 parts by mass of diethylene glycol monomethyl ether acetate were added and reacted at 110° C. for 3 hours. Next, 135 parts by mass of bisphenol F type epoxy resin (2) was added and reacted at 120° C. for 8 hours. Next, 72 parts by mass of succinic anhydride was added and reacted at 110 ° C. for 3 hours to obtain the desired acid group-containing acrylate resin (C2). The acid value of the solid content of the acid group-containing acrylate resin (C2) was 94 mgKOH/g.
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ビスフェノールA型エポキシ樹脂(1)188質量部、ジエチレングリコールモノメチルエーテルアセテート133質量部、ジブチルヒドロキシトルエン0.5質量部、メトキノン0.2質量部、アクリル酸72質量部、トリフェニルホスフィン1.3質量部を添加し、空気を吹き込みながら120℃で8時間反応させた。次いで、無水コハク酸50質量部を添加し、110℃で3時間反応させ、目的の酸基含有アクリレート樹脂(C3)を得た。この酸基含有アクリレート樹脂(C3)の固形分酸価は94mgKOH/gであった。 (Comparative Example 3: Production of Acid Group-Containing Acrylate Resin (C3))
In a flask equipped with a thermometer, a stirrer, and a reflux condenser, 188 parts by mass of bisphenol A type epoxy resin (1), 133 parts by mass of diethylene glycol monomethyl ether acetate, 0.5 parts by mass of dibutylhydroxytoluene, 0.2 parts by mass of metoquinone. Parts, 72 parts by mass of acrylic acid and 1.3 parts by mass of triphenylphosphine were added, and the mixture was reacted at 120 ° C. for 8 hours while blowing air. Next, 50 parts by mass of succinic anhydride was added and reacted at 110 ° C. for 3 hours to obtain the desired acid group-containing acrylate resin (C3). The acid value of the solid content of this acid group-containing acrylate resin (C3) was 94 mgKOH/g.
実施例1で得た酸基含有アクリレート樹脂(1)、硬化剤としてオルソクレゾールノボラック型エポキシ樹脂(DIC株式会社製「EPICLON N-680」)と、ジペンタエリスリトールヘキサアクリレートと、ジエチレングリコールモノエチルエーテルアセテートと、光重合開始剤(IGM社製「Omnirad 907」)と、2-エチル-4-メチルイミダゾールと、フタロシアニングリーンとを表1に示す質量部で配合し、ロールミルにより混錬して硬化性樹脂組成物(1)を得た。 (Example 23: Preparation of curable resin composition (1))
The acid group-containing acrylate resin (1) obtained in Example 1, an orthocresol novolac type epoxy resin (“EPICLON N-680” manufactured by DIC Corporation) as a curing agent, dipentaerythritol hexaacrylate, and diethylene glycol monoethyl ether acetate. , A photopolymerization initiator (“Omnirad 907” manufactured by IGM), 2-ethyl-4-methylimidazole, and phthalocyanine green were mixed in a mass part shown in Table 1 and kneaded by a roll mill to prepare a curable resin. A composition (1) was obtained.
実施例23で用いた酸基含有アクリレート樹脂(1)の代わりに、実施例2~21で得た酸基含有アクリレート樹脂(2)~(21)、または実施例22で得た酸基含有メタクリレート樹脂(1)をそれぞれ用いた以外は、実施例23と同様にして硬化性樹脂組成物(2)~(22)を得た。 (Examples 24-42: Preparation of curable resin compositions (2)-(22))
Instead of the acid group-containing acrylate resin (1) used in Example 23, the acid group-containing acrylate resins (2) to (21) obtained in Examples 2 to 21 or the acid group-containing methacrylate obtained in Example 22. Curable resin compositions (2) to (22) were obtained in the same manner as in Example 23 except that the resin (1) was used.
実施例23で用いた酸基含有アクリレート樹脂(1)の代わりに、実施例6で得た酸基含有アクリレート樹脂、及び合成例9で得た酸基含有アクリレート樹脂(P)を用いた以外は、実施例23と同様にして硬化性樹脂組成物(23)を得た。 (Example 43: Preparation of curable resin composition (23))
Except that the acid group-containing acrylate resin obtained in Example 6 and the acid group-containing acrylate resin (P) obtained in Synthesis Example 9 were used instead of the acid group-containing acrylate resin (1) used in Example 23. , A curable resin composition (23) was obtained in the same manner as in Example 23.
実施例21で用いた酸基含有アクリレート樹脂(1)の代わりに、比較例1~3で得た酸基含有アクリレート樹脂(C1)~(C3)をそれぞれ用いた以外は、実施例22と同様にして硬化性樹脂組成物(C4)~(C6)を得た。 (Comparative Examples 4 to 6: Preparation of curable resin compositions (C4) to (C6))
Similar to Example 22 except that the acid group-containing acrylate resins (C1) to (C3) obtained in Comparative Examples 1 to 3 were used instead of the acid group-containing acrylate resin (1) used in Example 21. The curable resin compositions (C4) to (C6) were obtained.
各実施例及び比較例で得られた硬化性樹脂組成物を、アプリケーターを用いてガラス基材上に膜厚50μmとなるように塗布した後、80℃でそれぞれ30分間乾燥させた。次いで、コダック社製のステップタブレットNo.2を介し、メタルハライドランプを用いて1000mJ/cm2の紫外線を照射した。これを1質量%の炭酸ナトリウム水溶液で180秒現像し、残存した段数で評価した。なお、残存段数が多いほど光感度が高い。 [Evaluation method of light sensitivity]
The curable resin compositions obtained in Examples and Comparative Examples were applied on a glass substrate with an applicator so as to have a film thickness of 50 μm, and then dried at 80° C. for 30 minutes each. Next, step tablet No. manufactured by Kodak Co., Ltd. Ultraviolet rays of 1000 mJ/cm 2 were radiated through the No. 2 through a metal halide lamp. This was developed with a 1% by mass aqueous sodium carbonate solution for 180 seconds and evaluated by the number of remaining stages. The higher the number of remaining steps, the higher the photosensitivity.
各実施例及び比較例で得られた硬化性樹脂組成物を、アプリケーターを用いてガラス基材上に膜厚50μmとなるように塗布した後、80℃でそれぞれ30分間、40分間、50分間、60分間乾燥させ、乾燥時間が異なるサンプルを作成した。これらを1%炭酸ナトリウム水溶液で30℃180秒間現像し、基板上に残渣が残らなかったサンプルの80℃での乾燥時間を乾燥管理幅として評価した。なお、乾燥管理幅が長いほどアルカリ現像性が優れていることを示す。 [Evaluation method of alkali developability]
The curable resin compositions obtained in each Example and Comparative Example were applied to a glass substrate using an applicator so as to have a film thickness of 50 μm, and then at 80 ° C. for 30 minutes, 40 minutes, and 50 minutes, respectively. The mixture was dried for 60 minutes to prepare samples having different drying times. These were developed with a 1% sodium carbonate aqueous solution at 30° C. for 180 seconds, and the drying time at 80° C. of the sample in which no residue remained on the substrate was evaluated as the drying control width. It should be noted that the longer the drying control range, the better the alkali developability.
実施例1で得た酸基含有アクリレート樹脂(1)、硬化剤としてオルソクレゾールノボラック型エポキシ樹脂(DIC株式会社製「EPICLON N-680」)、光重合開始剤として2-メチル-1-(4-メチルチオフェニル)-2-モルフォリノプロパン-1-オン(IGM社製「Omnirad-907」)、有機溶剤としてジエチレングリコールモノメチルエーテルアセテートを表3に示す質量部で配合して、硬化性樹脂組成物(24)を得た。 (Example 44: Preparation of curable resin composition (24))
The acid group-containing acrylate resin (1) obtained in Example 1, an orthocresol novolac type epoxy resin (“EPICLON N-680” manufactured by DIC Corporation) as a curing agent, and 2-methyl-1-(4 as a photopolymerization initiator. -Methylthiophenyl)-2-morpholinopropan-1-one ("OMNIRAD-907" manufactured by IGM) and diethylene glycol monomethyl ether acetate as an organic solvent in an amount of parts by mass shown in Table 3 to prepare a curable resin composition ( 24) was obtained.
実施例43で用いた酸基含有アクリレート樹脂(1)の代わりに、実施例2~21で得た酸基含有アクリレート樹脂(2)~(21)、または実施例22で得た酸基含有メタクリレート樹脂(1)をそれぞれ用いた以外は、実施例42と同様にして硬化性樹脂組成物(25)~(45)を得た。 (Examples 45 to 65: Preparation of curable resin compositions (25) to (45))
Instead of the acid group-containing acrylate resin (1) used in Example 43, the acid group-containing acrylate resins (2) to (21) obtained in Examples 2 to 21 or the acid group-containing methacrylate obtained in Example 22. Curable resin compositions (25) to (45) were obtained in the same manner as in Example 42, except that the resin (1) was used.
実施例44で用いた酸基含有アクリレート樹脂(1)の代わりに、実施例6で得た酸基含有アクリレート樹脂、及び合成例9で得た酸基含有アクリレート樹脂(P)を用いた以外は、実施例44と同様にして硬化性樹脂組成物(46)を得た。 (Example 66: Preparation of curable resin composition (46))
Except that the acid group-containing acrylate resin obtained in Example 6 and the acid group-containing acrylate resin (P) obtained in Synthesis Example 9 were used instead of the acid group-containing acrylate resin (1) used in Example 44. , A curable resin composition (46) was obtained in the same manner as in Example 44.
実施例44で用いた酸基含有アクリレート樹脂(1)の代わりに、比較例1~3で得た酸基含有アクリレート樹脂(C1)~(C3)をそれぞれ用いた以外は、実施例44と同様にして硬化性樹脂組成物(C7)~(C9)を得た。 (Comparative Examples 7 to 9: Preparation of Curable Resin Compositions (C7) to (C9))
Similar to Example 44 except that the acid group-containing acrylate resins (C1) to (C3) obtained in Comparative Examples 1 to 3 were used instead of the acid group-containing acrylate resin (1) used in Example 44, respectively. The curable resin compositions (C7) to (C9) were obtained.
伸度の測定は、引張試験に基づいて行った。
<試験片の作製>
ガラス基材上に実施例及び比較例で得られた硬化性樹脂組成物を50μmのアプリケーターで塗布し、80℃で30分間乾燥させた。メタルハライドランプを用いて1000mJ/cm2の紫外線を照射した後、160℃で1時間加熱した。ガラス基材から硬化物を剥離し、試験片(硬化物)を得た。 [Measurement method of elongation]
Elongation was measured based on a tensile test.
<Preparation of test piece>
The curable resin compositions obtained in Examples and Comparative Examples were applied on a glass substrate with an applicator of 50 μm and dried at 80° C. for 30 minutes. After irradiating with 1000 mJ/cm< 2 > ultraviolet rays using a metal halide lamp, it heated at 160 degreeC for 1 hour. The cured product was peeled off from the glass substrate to obtain a test piece (cured product).
前記試験片2を10mm×80mmの大きさに切り出し、株式会社島津製作所製精密万能試験機オートグラフ「AG-IS」を用いて、下記の測定条件で試験片の引張試験を行った。試験片が破断するまでの伸度(%)を測定し、以下の基準に従い評価した。 <Tensile test>
The test piece 2 was cut into a size of 10 mm × 80 mm, and a tensile test of the test piece was performed under the following measurement conditions using a precision universal testing machine Autograph “AG-IS” manufactured by Shimadzu Corporation. The elongation (%) until the test piece broke was measured and evaluated according to the following criteria.
Claims (14)
- エポキシ樹脂(A)、不飽和一塩基酸(B)、及び多塩基酸無水物(C)の反応物(I)と、
エポキシ樹脂(D)と、
不飽和一塩基酸(E)と、
を必須の反応原料とすることを特徴とする酸基含有(メタ)アクリレート樹脂。 A reaction product (I) of an epoxy resin (A), an unsaturated monobasic acid (B), and a polybasic acid anhydride (C),
Epoxy resin (D) and
Unsaturated monobasic acid (E),
An acid group-containing (meth) acrylate resin, which comprises an essential reaction raw material. - 前記反応物(I)が有する酸基1モルに対して、前記エポキシ樹脂(D)が有するエポキシ基のモル数が、0.3~0.8の範囲である請求項1記載の酸基含有(メタ)アクリレート樹脂。 The acid group-containing product according to claim 1, wherein the number of moles of the epoxy group contained in the epoxy resin (D) is in the range of 0.3 to 0.8 with respect to 1 mole of the acid group contained in the reaction product (I). (Meth)acrylate resin.
- 前記酸基含有(メタ)アクリレート樹脂が、前記反応物(I)と、前記エポキシ樹脂(D)及び前記不飽和一塩基酸(E)の反応物(II)とを必須の反応原料とするものである請求項1記載の酸基含有(メタ)アクリレート樹脂。 The acid group-containing (meth)acrylate resin uses the reactant (I) and the reactant (II) of the epoxy resin (D) and the unsaturated monobasic acid (E) as essential reaction raw materials. The acid group-containing (meth)acrylate resin according to claim 1, which is
- 前記反応物(I)が有する酸基1モルに対して、前記反応物(II)が有するエポキシ基のモル数が、0.05~0.4の範囲である請求項3記載の酸基含有(メタ)アクリレート樹脂。 The acid group-containing product according to claim 3, wherein the number of moles of the epoxy group contained in the reaction product (II) is in the range of 0.05 to 0.4 with respect to 1 mol of the acid group contained in the reaction product (I). (Meth)acrylate resin.
- 前記エポキシ樹脂(D)が有するエポキシ基1モルに対して、前記不飽和一塩基酸(E)が有する酸基のモル数が、0.25~0.75の範囲である請求項3記載の酸基含有(メタ)アクリレート樹脂。 4. The number of moles of acid groups in the unsaturated monobasic acid (E) is in the range of 0.25 to 0.75 with respect to 1 mole of epoxy groups in the epoxy resin (D). Acid group-containing (meth)acrylate resin.
- 前記反応物(II)が、同一分子内にエポキシ基及び(メタ)アクリロイル基を有するものである請求項3記載の酸基含有(メタ)アクリレート樹脂。 The acid group-containing (meth)acrylate resin according to claim 3, wherein the reaction product (II) has an epoxy group and a (meth)acryloyl group in the same molecule.
- 前記エポキシ樹脂(D)のエポキシ当量が、180g/当量以下である請求項1~6のいずれか1項記載の酸基含有(メタ)アクリレート樹脂。 The acid group-containing (meth)acrylate resin according to any one of claims 1 to 6, wherein the epoxy equivalent of the epoxy resin (D) is 180 g/equivalent or less.
- 請求項1~7のいずれか1項記載の酸基含有(メタ)アクリレート樹脂と、光重合開始剤とを含有することを特徴とする硬化性樹脂組成物。 A curable resin composition comprising the acid group-containing (meth)acrylate resin according to any one of claims 1 to 7 and a photopolymerization initiator.
- さらに、有機溶剤と、硬化剤とを含有するものである請求項8記載の硬化性樹脂組成物。 The curable resin composition according to claim 8, further comprising an organic solvent and a curing agent.
- さらに、請求項1~7のいずれか1項記載の酸基含有(メタ)アクリレート樹脂以外の酸基及び重合性不飽和結合を有する樹脂(F)を含有するものである請求項6記載の硬化性樹脂組成物。 The curing according to claim 6, further comprising a resin (F) having an acid group and a polymerizable unsaturated bond other than the acid group-containing (meth)acrylate resin according to any one of claims 1 to 7. Resin composition.
- 請求項8~10のいずれか1項記載の硬化性樹脂組成物の硬化反応物であることを特徴とする硬化物。 A cured product, which is a cured reaction product of the curable resin composition according to any one of claims 8 to 10.
- 請求項8~10のいずれか1項記載の硬化性樹脂組成物からなることを特徴とする絶縁材料。 An insulating material comprising the curable resin composition according to any one of claims 8 to 10.
- 請求項8~10のいずれか1項記載の硬化性樹脂組成物からなることを特徴とするソルダーレジスト用樹脂材料。 A resin material for solder resist, which comprises the curable resin composition according to any one of claims 8 to 10.
- 請求項13記載のソルダーレジスト用樹脂材料からなることを特徴とするレジスト部材。 A resist member comprising the resin material for solder resist according to claim 13.
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JP2020535670A JP6813135B1 (en) | 2019-03-06 | 2020-01-28 | Acid group-containing (meth) acrylate resin, curable resin composition, cured product, insulating material, resin material for solder resist and resist member |
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JPH0987346A (en) * | 1995-09-19 | 1997-03-31 | Dainippon Ink & Chem Inc | Energy ray curing epoxyacrylate resin composition |
JP2000267275A (en) * | 1999-03-15 | 2000-09-29 | Tamura Kaken Co Ltd | Photosensitive resin composition and printed circuit board |
JP2004131526A (en) * | 2002-10-08 | 2004-04-30 | Great Eastern Resins Industrial Co Ltd | Photosensitive thermosetting resin and method for producing the same and solder-resistant ink composition comprising the resin |
JP2007003590A (en) * | 2005-06-21 | 2007-01-11 | Dainippon Ink & Chem Inc | Resist ink composition |
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JPS61243869A (en) | 1985-04-19 | 1986-10-30 | Taiyo Ink Seizo Kk | Resist ink composition |
JP4242010B2 (en) * | 1999-06-30 | 2009-03-18 | 日本化薬株式会社 | Photosensitive resin composition and cured product thereof |
KR101515679B1 (en) * | 2008-06-09 | 2015-04-27 | 고오 가가쿠고교 가부시키가이샤 | Carboxyl group-containing resin, curable composition containing carboxyl group-containing resin, and cured product of the composition |
CN110461900B (en) * | 2017-04-06 | 2022-03-18 | Dic株式会社 | Acid group-containing (meth) acrylate resin and resin material for solder resist |
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JPH0987346A (en) * | 1995-09-19 | 1997-03-31 | Dainippon Ink & Chem Inc | Energy ray curing epoxyacrylate resin composition |
JP2000267275A (en) * | 1999-03-15 | 2000-09-29 | Tamura Kaken Co Ltd | Photosensitive resin composition and printed circuit board |
JP2004131526A (en) * | 2002-10-08 | 2004-04-30 | Great Eastern Resins Industrial Co Ltd | Photosensitive thermosetting resin and method for producing the same and solder-resistant ink composition comprising the resin |
JP2007003590A (en) * | 2005-06-21 | 2007-01-11 | Dainippon Ink & Chem Inc | Resist ink composition |
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