JP2017190403A - エポキシ樹脂、反応性カルボキシレート化合物、それを用いた硬化型樹脂組成物、及びその用途 - Google Patents
エポキシ樹脂、反応性カルボキシレート化合物、それを用いた硬化型樹脂組成物、及びその用途 Download PDFInfo
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- JP2017190403A JP2017190403A JP2016080934A JP2016080934A JP2017190403A JP 2017190403 A JP2017190403 A JP 2017190403A JP 2016080934 A JP2016080934 A JP 2016080934A JP 2016080934 A JP2016080934 A JP 2016080934A JP 2017190403 A JP2017190403 A JP 2017190403A
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- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- DNWBGZGLCKETOT-UHFFFAOYSA-N cyclohexane;1,3-dioxane Chemical compound C1CCCCC1.C1COCOC1 DNWBGZGLCKETOT-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
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- 238000005530 etching Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- PQDRJEDWHXYDCQ-UHFFFAOYSA-L fluoro-dioxido-oxo-lambda5-phosphane 4-methoxybenzenediazonium Chemical compound [O-]P([O-])(F)=O.COc1ccc(cc1)[N+]#N.COc1ccc(cc1)[N+]#N PQDRJEDWHXYDCQ-UHFFFAOYSA-L 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
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- 238000010030 laminating Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
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- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 238000000465 moulding Methods 0.000 description 1
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
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- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus 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
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- VPMTUQQBSUTFJT-UHFFFAOYSA-N propan-2-amine;dihydrochloride Chemical compound Cl.Cl.CC(C)N VPMTUQQBSUTFJT-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-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
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1466—Acrylic or methacrylic acids
-
- 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
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/064—Polymers containing more than one epoxy group per molecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
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- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/302—General preparatory processes using carbonates and cyclic ethers
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- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/10—Epoxy resins modified by unsaturated compounds
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- 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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Abstract
Description
更には、該反応性エポキシカルボキシレート化合物(A)及び(A’)、反応性ポリカルボン酸化合物(B)及び(B’)が着色顔料との良好な親和性を有していることを見出し、これらの化合物を含む組成物が高い顔料濃度でも良好な現像性を持つレジスト材料等となることを見出した。
さらに前記多環式炭化水素基を有するエポキシ樹脂(a)と一分子中に重合可能なエチレン性不飽和基とカルボキシ基を併せ持つ化合物(b)と多塩基酸無水物(d)を反応させて得られる反応性エポキシカルボキシレート化合物(A’)に関する。
さらに前記カルボキシレート化合物(A’)に多塩基酸無水物(d)を反応せしめて得られる反応性ポリカルボン酸化合物(B’)に関する。
さらに、前記カルボキシレート化合物(A)を含む活性エネルギー線硬化型樹脂組成物に関する。
さらに、反応性ポリカルボン酸化合物(B)を含む活性エネルギー線硬化型樹脂組成物に関する。
さらに、前記カルボキシレート化合物(A)及び/又は(B)を含む活性エネルギー線硬化型樹脂組成物に関する。
さらに、前記カルボキシレート化合物(A’)を含む活性エネルギー線硬化型樹脂組成物に関する。
さらに、前記反応性ポリカルボン酸化合物(B’)を含む活性エネルギー線硬化型樹脂組成物に関する。
さらに、前記カルボキシレート化合物(A’)及び/又は(B’)を含む活性エネルギー線硬化型樹脂組成物に関する。
さらに、反応性エポキシカルボキシレート化合物(A)、反応性エポキシカルボキシレート化合物(A’)、反応性ポリカルボン酸化合物(B)、反応性ポリカルボン酸化合物(B’)から選ばれる2種以上を含む活性エネルギー線硬化型樹脂組成物に関する。
さらに、反応性化合物(C)を含む前記活性エネルギー線硬化型樹脂組成物に関する。
さらに、着色顔料を含有する前記活性エネルギー線硬化型樹脂組成物に関する。
さらに、成形用材料である前記活性エネルギー線硬化型樹脂組成物に関する。
さらに、皮膜形成用材料である前記活性エネルギー線硬化型樹脂組成物に関する。
さらに、レジスト材料組成物である前記活性エネルギー線硬化型樹脂組成物に関する。
さらに、前記活性エネルギー線硬化型樹脂組成物の硬化物に関する。
さらに、前記硬化物でオーバーコートされた物品に関する。
さらに、前記エポキシ樹脂(a)一分子中に重合可能なエチレン性不飽和基とカルボキシ基を併せ持つ化合物(b)と一分子中に二つ以上のカルボキシ基を併せ持つ化合物(c)を反応させて得られる反応性エポキシカルボキシレート化合物(A)の製造法に関する。
さらに前記エポキシ樹脂(a)と一分子中に重合可能なエチレン性不飽和基とカルボキシ基を併せ持つ化合物(b)と多塩基酸無水物(d)を反応させて得られる反応性エポキシカルボキシレート化合物(A’)の製造法に関する。
さらに、前記カルボキシレート化合物(A)と多塩基酸無水物(d)を反応させる反応性ポリカルボン酸化合物(B)の製造法に関する。
さらに、前記カルボキシレート化合物(A’)と多塩基酸無水物(d)を反応させる反応性ポリカルボン酸化合物(B’)の製造法に関する。
1)エポキシ当量:JISK−7236:2001に準じた方法で測定した。
2)水酸基当量:該当するエポキシ樹脂のエポキシ当量と、エポキシ樹脂中のエポキシ基と当量の酢酸を反応させ、エポキシ基を開環させた後、JIS K 0070:1992に準じた方法で測定して得られた水酸基当量から算出した。
3)GPCの測定条件は以下の通りである。
機種:TOSOH HLC−8220GPC
カラム:Super HZM−N
溶離液:THF(テトラヒドロフラン); 0.35ml/分、40℃
検出器:示差屈折計
分子量標準:ポリスチレン
撹拌機、還流冷却管、撹拌装置を備えたフラスコに、窒素パージを施しながら前記式(1)のエポキシ樹脂(a)としてフェノール−ビフェニルノボラック型エポキシ樹脂(日本化薬(株)製 NC−3500;エポキシ当量207g/eq.、軟化点70℃、)、分子中に一個以上の重合可能なエチレン性不飽和基と一個以上のカルボキシ基を併せ持つ化合物(b)としてアクリル酸(Mw=72)を表1に記載量、(c)としてテトラヒドロフタル酸(Mw=170)もしくは(d)としてテトラヒドロ無水フタル酸(Mw=152)を表1に記載量、及び、触媒としてトリフェニルホスフィン3g、溶剤としてプロピレングリコールモノメチルエーテルモノアセテートを固形分60%となるように加え、100℃において24時間反応させ、反応性カルボキシレート化合物(A)及び(A’)溶液、並びに比較例の化合物を得た。
実施例1及び比較例1において合成した反応性カルボキシレート化合物(A)/(A’)溶液251gに多塩基酸無水物(d)として、テトラヒドロ無水フタル酸を表2に記載量、及び溶剤として固形分が65質量部となるようプロピレングリコールモノメチルエーテルモノアセテートを添加し、100℃に加熱し酸付加反応させ反応性ポリカルボン酸化合物(B)及び(B’)溶液を得た。
実施例1及び比較例1において合成した反応性カルボキシレート化合物(A)/(A’)20g、ラジカル硬化型の単量体(C)であるジペンタエリスリトールヘキサアクリレート4g、紫外線反応型開始剤としてイルガキュア184を1.5g混合し、加熱溶解した。
さらにこれを、乾燥時の膜厚20μmになるようハンドアプリケータによってポリカーボネート板上に塗工し、80℃で30分間、電気オーブンにて溶剤乾燥を実施した。乾燥後、高圧水銀ランプを具備した紫外線垂直露光装置((株)オーク製作所製)によって照射線量1000mJの紫外線を照射、硬化させ樹脂組成物でオーバーコートされた物品を得た。
この樹脂組成物でオーバーコートされた物品の塗膜の硬度をJIS K5600−5−4:1999により測定し、さらに耐衝撃性の試験をISO6272−1:2002によって実施した。
○:傷、はがれなし。
△:僅かに傷あり。
×:剥がれた。
実施例2で合成した反応性ポリカルボン酸化合物(B)/(B’)を56.73g、その他反応性化合物(C)としてDPCA−60(商品名:日本化薬(株)製 多官能アクリレート単量体)5.67g、光重合開始剤としてイルガキュア907(チバスペシャリチィーケミカルズ製)を2.92g及びカヤキュアーDETX−S(日本化薬(株)製)を0.58g、硬化成分としてNC−3000H(日本化薬(株)製)を17.54g、熱硬化触媒としてメラミンを0.73g及び濃度調整溶媒としてプロピレングリコールモノメチルエーテルモノアセテートを5.67g加え、ビーズミルにて混練し均一に分散させレジスト樹脂組成物を得た。得られた組成物をワイヤーバーコーター♯20を用い、支持フィルムとなるポリエチレンテレフタレートフィルムに均一に塗布し、温度70℃の熱風乾燥炉を通過させ、厚さ20μmの樹脂層を形成した後、この樹脂層上に保護フィルムとなるポリエチレンフィルムを貼り付け、ドライフィルムを得た。得られたドライフィルムをポリイミドプリント基板(銅回路厚:12μm、ポリイミドフィルム厚:25μm)に、温度80℃の加熱ロールを用いて、保護フィルムを剥離しながら樹脂層を基板全面に貼り付けた。
感度は、ステップタブレットを透過した露光部に、何段目の濃度部分までが現像時に残存したかで判定した。段数(値)が大きいほうがタブレットの濃部で高感度と判定される(単位:段)。
現像性は、パターンマスクを透過した露光部を現像する際に、パターン形状部が完全に現像されきるまでの時間、いわゆるブレイクタイムをもって現像性の評価とした(単位:秒)。
硬化性評価は、150℃加熱終了後の硬化膜の鉛筆硬度をもって示した。
評価方法は、JIS K5600−5−4:1999に準拠した。
レジストの硬化膜を形成したポリイミドプリント基板を、硬化膜側を上にして山折りし、指で折り曲げ部をよくしごいた。折り曲げ部を元に戻し、レジスト膜をルーペで観察した。
○:亀裂なし
△:僅かな亀裂が観察される
×:剥離する
実施例2で得られた反応性ポリカルボン酸化合物(B)及び(B’)を20g、その他反応性化合物(C)としてDPHA(商品名:日本化薬(株)製 アクリレート単量体)5.0g、有機溶剤としてプロピレングリコールモノメチルエーテルアセテート10g、着色顔料として三菱カーボンブラック MA−100:10gを混合攪拌した。そこに35gのガラスビーズを入れ、ペイントシェーカで1時間分散を行った。
分散終了後の分散液を、ワイヤーバーコーター#2でポリエチレンテレフタレートフィルム上に塗工し、80℃の温風乾燥機で10分間乾燥を行った。
乾燥終了後の塗膜表面の光沢を、60°反射グロス計を用いて測定し、カーボンブラックの分散性を評価した。表7に結果を示す。光沢の値が高いほど良好な顔料分散性を示す。
実施例4で調製したレジスト組成物10.0g、リン系反応性難燃剤(FRM−1000日本化薬(株)製)0.5gを混合攪拌し、硬化型樹脂組成物を得た。組成物を膜厚25μmのポリイミドフィルムに、ワイヤーバーコーター#20で塗工、温度70℃の熱風乾燥炉を通過させ、厚さおおよそ15μmの樹脂層を形成した。紫外線露光装置((株)オーク製作所、型式HMW−680GW)を用い500mJ/cm2の紫外線を照射した。照射後、プリント基板を150℃の熱風乾燥器で60分加熱硬化反応させて硬化膜を得た。得られた硬化膜を、長さ20cm、幅2cmの短冊状にポリイミド基材フィルムと一緒に切り出した。切り出したフィルムを縦長に吊るし、下端よりライターによって火をつけ、難燃性を評価した。本願発明の硬化膜は着火するものの、全焼する前に消火する難燃性を示した。
Claims (10)
- 下記一般式(1)で表されるエポキシ樹脂(a)と一分子中に重合可能なエチレン性不飽和基とカルボキシ基を併せ持つ化合物(b)と多塩基酸無水物(d)を反応させて得られる反応性エポキシカルボキシレート化合物(A’)。
- 請求項1記載のカルボキシレート化合物(A)と多塩基酸無水物(d)とを反応せしめて得られる反応性ポリカルボン酸化合物(B)。
- 請求項1に記載のカルボキシレート化合物(A)及び/又は請求項3に記載の反応性ポリカルボン酸化合物(B)を含む活性エネルギー線硬化型樹脂組成物。
- さらに反応性化合物(C)を含む請求項4に記載の活性エネルギー線硬化型樹脂組成物。
- 請求項2に記載のカルボキシレート化合物(A’)に多塩基酸無水物(d)を反応せしめて得られる反応性ポリカルボン酸化合物(B’)。
- 請求項2に記載のカルボキシレート化合物(A’)及び/又は請求項6に記載の反応性ポリカルボン酸化合物(B’)を含む活性エネルギー線硬化型樹脂組成物。
- さらに反応性化合物(C)を含む請求項7に記載の活性エネルギー線硬化型樹脂組成物。
- 請求項4、5、7乃至8のいずれか一項に記載の活性エネルギー線硬化型樹脂組成物の硬化物。
- 請求項9に記載の硬化物を有する物品。
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