CN118146669A - Bio-based low-dielectric solder resist ink and preparation method and application thereof - Google Patents
Bio-based low-dielectric solder resist ink and preparation method and application thereof Download PDFInfo
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- CN118146669A CN118146669A CN202410334776.0A CN202410334776A CN118146669A CN 118146669 A CN118146669 A CN 118146669A CN 202410334776 A CN202410334776 A CN 202410334776A CN 118146669 A CN118146669 A CN 118146669A
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- resist ink
- resin
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- 229910000679 solder Inorganic materials 0.000 title claims abstract description 73
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 229920005989 resin Polymers 0.000 claims abstract description 66
- 239000011347 resin Substances 0.000 claims abstract description 66
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 55
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 46
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims abstract description 41
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000000945 filler Substances 0.000 claims abstract description 31
- 239000002994 raw material Substances 0.000 claims abstract description 21
- 239000003822 epoxy resin Substances 0.000 claims abstract description 15
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 15
- 239000003999 initiator Substances 0.000 claims abstract description 14
- -1 diallyl epoxy acrylate Chemical compound 0.000 claims abstract description 11
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 67
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 238000010438 heat treatment Methods 0.000 claims description 50
- 238000003756 stirring Methods 0.000 claims description 50
- 238000006116 polymerization reaction Methods 0.000 claims description 42
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 36
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 claims description 31
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 29
- 239000004841 bisphenol A epoxy resin Substances 0.000 claims description 25
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 21
- 239000003112 inhibitor Substances 0.000 claims description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 18
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 17
- 239000012986 chain transfer agent Substances 0.000 claims description 11
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 10
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 10
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 7
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 claims description 6
- 230000001681 protective effect Effects 0.000 claims description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 239000004842 bisphenol F epoxy resin Substances 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 abstract description 7
- 239000002028 Biomass Substances 0.000 abstract description 3
- 239000000976 ink Substances 0.000 description 55
- 238000001723 curing Methods 0.000 description 28
- 239000003085 diluting agent Substances 0.000 description 25
- 239000000049 pigment Substances 0.000 description 25
- 239000002270 dispersing agent Substances 0.000 description 24
- 238000000227 grinding Methods 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000002518 antifoaming agent Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 235000012239 silicon dioxide Nutrition 0.000 description 10
- AEUVIXACNOXTBX-UHFFFAOYSA-N 1-sulfanylpropan-1-ol Chemical compound CCC(O)S AEUVIXACNOXTBX-UHFFFAOYSA-N 0.000 description 9
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 239000013530 defoamer Substances 0.000 description 8
- 238000004321 preservation Methods 0.000 description 8
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 7
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000010907 mechanical stirring Methods 0.000 description 7
- 239000004743 Polypropylene Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 3
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- 150000003797 alkaloid derivatives Chemical class 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 150000007974 melamines Chemical class 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical group O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- XNYMEGZIZQYIEX-UHFFFAOYSA-N furan;prop-2-enoic acid Chemical compound C=1C=COC=1.OC(=O)C=C XNYMEGZIZQYIEX-UHFFFAOYSA-N 0.000 description 1
- 238000007542 hardness measurement Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000001038 titanium pigment Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- 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
- C08G59/14—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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Epoxy Resins (AREA)
Abstract
The invention discloses a bio-based low dielectric solder resist ink, a preparation method and application thereof. The raw materials of the solder resist ink comprise the following components: a bio-based alkali-soluble resin; an epoxy resin containing at least a diallyl type epoxy acrylate resin; a curing agent; a photoinitiator; a filler; an auxiliary agent; the structural formula of the bio-based alkali-soluble resin is as follows: Wherein x, y, z and m > 0; the structural formula of the diallyl epoxy acrylate resin is as follows:
Description
Technical Field
The invention relates to the technical field of solder resist ink, in particular to a bio-based low-dielectric solder resist ink and a preparation method and application thereof.
Background
The solder resist ink is mainly used for coating a solder resist coating on a circuit board to avoid short circuit caused by soldering, thereby saving solder, improving the welding efficiency, preventing the circuit from being oxidized due to invasion of moisture and electrolyte, avoiding mechanical abrasion to damage the circuit and realizing insulation protection. In order to meet the requirements of the PCB manufacturing process, the solder resist ink is required to have excellent photosensitivity, developability, resolution, heat resistance and low dielectric constant.
Solder resist ink is typically composed of a matrix resin, reactive diluents, initiators, curing agents, pigments, fillers, adjuvants, and the like. The matrix resin has the highest proportion in the formula and is also the most important component, and the structure directly determines the performance of the solder resist ink. However, at present, some conventional solder resist ink generally has a problem of too high dielectric constant, which limits the application range of the solder resist ink in the technical fields with high requirements such as 5G communication technology.
To reduce the dielectric constant of solder resist inks, there are generally two methods: firstly, preparing novel matrix resin with low dielectric constant, and secondly, selecting filler with low dielectric constant to reduce the dielectric constant of the formula system. Although the existing solder resist ink meets the requirements of the preparation process to a certain extent, the problem of too high dielectric constant exists in the traditional product generally, and the application of the solder resist ink in the emerging technical field is limited. To solve this problem, a new low dielectric resistance solder ink needs to be developed to improve the performance and application range of the solder ink.
Disclosure of Invention
The first technical problem to be solved by the invention is as follows:
A solder resist ink is provided.
The second technical problem to be solved by the invention is as follows:
A preparation method of the solder resist ink is provided.
In order to solve the first technical problem, the invention adopts the following technical scheme:
The raw materials of the solder resist ink comprise the following components:
A bio-based alkali-soluble resin;
an epoxy resin containing at least a diallyl type epoxy acrylate resin;
A curing agent;
A photoinitiator;
a filler;
An auxiliary agent;
the structural formula of the bio-based alkali-soluble resin is as follows:
wherein x, y, z and m > 0;
The structural formula of the diallyl epoxy acrylate resin is as follows:
According to the embodiments of the present invention, one of the technical solutions has at least one of the following advantages or beneficial effects:
The alkali-soluble resin in the matrix resin used in the solder resist ink takes biomass raw materials as a main initiator, and the diallyl type epoxy acrylate resin contains a structure capable of reducing dielectric property.
The invention adopts the bio-based alkali-soluble resin with furan structure and the novel diallyl type epoxy acrylate resin, and uses the bio-based alkali-soluble resin and the novel diallyl type epoxy acrylate resin as matrix resin to prepare the solder resist ink, which has good comprehensive performance, adhesive force, heat resistance and dielectric property.
The novel diallyl epoxy acrylate resin adopted by the invention has the advantages that the conjugated allyl structure in the structure can provide good electron conductivity, has certain reactivity, and can endow the resin with photo-curing activity together with acrylate double bonds; the furan heterocycle in the bio-based alkali-soluble resin has the characteristics of good stability and physical and chemical properties, the epoxy group has thermosetting activity, and can participate in post-hardening together with the epoxy resin in the ink formula, and the generated epoxy crosslinking network and the double bond crosslinking network can form an interpenetrating structure, so that the physical and chemical properties of a cured product are improved.
According to one embodiment of the invention, the raw materials of the solder resist ink comprise the following components in parts by weight:
10-40 parts of bio-based alkali-soluble resin;
15-60 parts of epoxy resin; the epoxy resin at least contains 10-40 parts of diallyl type epoxy acrylate resin;
2-6 parts of curing agent;
3-10 parts of photoinitiator;
5-15 parts of filler;
And 7-31 parts of auxiliary agent.
According to one embodiment of the present invention, the epoxy resin further comprises at least one of bisphenol a epoxy resin, bisphenol F epoxy resin, diallyl bisphenol a epoxy resin, novolac epoxy resin.
According to one embodiment of the present invention, the photoinitiator comprises at least one of 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholino-1-propanone, benzildimethyl ether, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, benzophenone and 2, 4-diethylthioxanthone.
According to one embodiment of the invention, the curing agent comprises at least one of dicyandiamide, 4' -diaminodiphenylmethane, phenylguanidine, and methylated melamine.
According to one embodiment of the invention, the filler comprises at least one of talc, barium sulfate, calcium carbonate, silica.
According to one embodiment of the invention, the auxiliary agent comprises at least one of reactive diluents, pigments, dispersants, leveling agents and defoamers.
According to one embodiment of the invention, the reactive diluent is present in the raw material of the solder resist ink in an amount of 5 to 20 parts by weight.
According to one embodiment of the invention, the reactive diluent comprises at least one of isobornyl acrylate, tripropylene glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate and dipentaerythritol hexaacrylate.
According to one embodiment of the invention, the pigment is present in the raw material of the solder resist ink in an amount of 5 to 15 parts by weight.
According to one embodiment of the invention, the pigment comprises at least one of phthalocyanine green, phthalocyanine blue, permanent violet, benzidine yellow, titanium pigment.
According to one embodiment of the present invention, the dispersant is 0.1 to 1 part by weight in the raw material of the solder resist ink.
According to one embodiment of the invention, the dispersant comprises at least one of di-height 1010, 630, 650, 671, 685.
According to one embodiment of the invention, the leveling agent is 0.1-1 part by weight in the raw materials of the solder resist ink.
According to one embodiment of the invention, the leveling agent comprises at least one of the digao 360, 604, 607, 960, 980.
According to one embodiment of the present invention, the defoaming agent is 0.1 to 1 part by weight in the raw materials of the solder resist ink.
According to one embodiment of the invention, the defoamer comprises at least one of the diegae 910, 921, 944, 963, 971.
According to one embodiment of the present invention, the preparation method of the bio-based alkali-soluble resin comprises the steps of:
S1, mixing furan methyl glycidyl ether, acrylic acid, a catalyst and a polymerization inhibitor, and cooling after heating reaction to obtain acrylic acid ester furan methyl glycidyl ether;
S2, introducing protective atmosphere into a reaction container, heating, adding propylene glycol methyl ether, the acrylated furan methyl glycidyl ether obtained in the step S1, glycidyl methacrylate, styrene, acrylic acid, a chain transfer agent and an initiator, preserving heat after the addition, and carrying out polymerization reaction to obtain a mixture;
And S3, after the polymerization reaction in the step S2 is finished, heating the mixture for reaction to obtain the bio-based alkali-soluble resin.
In the preparation method of the bio-based alkali-soluble resin, the raw materials of the bio-based alkali-soluble resin adopt the furan methyl glycidyl ether which is derived from biomass, and the bio-based alkali-soluble resin has wide sources, low cost and environmental protection, so that the bio-based alkali-soluble resin has good economic benefit and application prospect.
In the preparation method of the bio-based alkali-soluble resin, a protective atmosphere is introduced in step S2 to remove residual oxygen in a reaction system, ensure the reaction direction and avoid the influence of the residual oxygen on a product structure.
In the preparation method of the bio-based alkali-soluble resin, the protective atmosphere introducing amount is added in the step S3,
According to one embodiment of the present invention, in the step S1, the protective atmosphere includes N 2.
According to one embodiment of the present invention, in the step S1, the temperature after the temperature rise is 110-120 ℃, the heat preservation reaction is performed after the temperature rise, and the time of the heat preservation reaction is 6-8 hours.
According to one embodiment of the present invention, in the step S1, the polymerization inhibitor includes para-hydroxyanisole.
According to one embodiment of the invention, in the step S1, the catalyst comprises tetrabutylammonium bromide.
According to one embodiment of the present invention, the ratio of the temperature after the temperature rise in the step S2 to the temperature after the temperature rise in the step S3 is 70-80℃:90-100 ℃.
According to one embodiment of the present invention, in the step S2, the chain transfer agent includes mercaptopropanol.
According to one embodiment of the invention, in the step S2, the initiator comprises azobisisoheptonitrile.
According to one embodiment of the present invention, the preparation method of the bio-based alkali-soluble resin comprises the steps of:
S1, mixing furan methyl glycidyl ether, acrylic acid, tetrabutylammonium bromide serving as a catalyst and p-hydroxyanisole serving as a polymerization inhibitor, stirring, heating to 110-120 ℃, carrying out heat preservation reaction for 6-8h, and cooling to obtain acrylic acid ester furan methyl glycidyl ether;
S2, adding propylene glycol methyl ether into a reaction container, stirring, introducing N 2 for at least 1h, heating to 70-80 ℃, dropwise adding propylene glycol methyl ether, the mixture of the acrylic acid furan methyl glycidyl ether, glycidyl methacrylate, styrene, acrylic acid, chain transfer agent mercaptopropanol and initiator azo-diisoheptonitrile, which is obtained in the step S1, wherein the dropwise adding time is controlled to be 2-3h, and after the dropwise adding is finished, preserving heat, and carrying out polymerization for 3-4h to obtain a mixture;
And S3, after the polymerization reaction in the step S2 is finished, increasing the introducing amount of N 2, and heating the mixture to 90-100 ℃ to continue the reaction for 2-3 hours to obtain the alkaloid soluble resin.
In the step S2, N 2 is introduced for at least 1h, so that the deoxidizing efficiency and effect are ensured, the deoxidizing effect is poor due to too short time, and the efficiency is poor due to too long time.
In step S3, the amount of N 2 introduced is increased, and if the amount of N 2 introduced is not increased, the polymerization degree and/or the reaction degree of the reaction are/is affected.
According to one embodiment of the invention, in step S3, the N 2 feed is increased by 100-120%.
According to one embodiment of the present invention, the preparation method of the bio-based alkali-soluble resin comprises the steps of:
S1, mixing 154-160 parts of furan methyl glycidyl ether, 72-80 parts of acrylic acid, 0.1-1 part of catalyst tetrabutylammonium bromide and 0.01-0.05 part of polymerization inhibitor p-hydroxyanisole, stirring, heating to 110-120 ℃, carrying out heat preservation reaction for 6-8 hours, and cooling to obtain acrylic acid ester furan methyl glycidyl ether;
S2, adding 30-100 parts of propylene glycol methyl ether into a reaction container, stirring, introducing N 2, heating to 70 ℃ after at least 1h, dropwise adding 50-200 parts of propylene glycol methyl ether, 30-50 parts of the mixture of the acrylated furan methyl glycidyl ether obtained in the step S1, 10-25 parts of glycidyl methacrylate, 10-30 parts of styrene, 15-35 parts of acrylic acid, 0.1-1 part of chain transfer agent mercaptopropanol and 0.5-2 parts of initiator azo-diisoheptonitrile, keeping the temperature after the dropwise adding is finished, and carrying out polymerization for 3-4h to obtain a mixture;
And S3, after the polymerization reaction in the step S2 is finished, increasing the introducing amount of N 2, and heating the mixture to 90-100 ℃ to continue the reaction for 2-3 hours to obtain the alkaloid soluble resin. Wherein the raw materials are in parts by weight.
According to one embodiment of the invention, the preparation method of the diallyl type epoxy acrylate resin comprises the following steps:
A1, mixing diallyl bisphenol A epoxy resin, a polymerization inhibitor p-hydroxyanisole and a catalyst triphenylphosphine, and heating to react to obtain a mixture;
a2, controlling the temperature of a reaction system to be not more than 115 ℃, adding acrylic acid into the mixture, and then heating to react to obtain the diallyl type epoxy acrylate resin.
According to one embodiment of the invention, the preparation method of the diallyl type epoxy acrylate resin comprises the following steps:
a1, mixing 420-450 parts of diallyl bisphenol A epoxy resin, 0.05-0.15 part of polymerization inhibitor p-hydroxyanisole and 2-5.5 parts of catalyst triphenylphosphine, stirring, and heating to 100-110 ℃ to obtain a mixture;
And A2, dropwise adding 130-145 parts of acrylic acid, controlling the temperature of a reaction system to be not more than 115 ℃ in the dropwise adding process, heating to 110-120 ℃ after the dropwise adding is finished, carrying out heat preservation reaction for 4-5h, and cooling to obtain the diallyl type epoxy acrylate resin.
In order to solve the second technical problem, the invention adopts the following technical scheme:
a method of preparing the solder mask ink comprising the steps of:
b1, mixing the bio-based alkali-soluble resin, the epoxy resin and the filler in a container, heating and stirring to obtain a mixture;
And B2, adding a photoinitiator and a curing agent into the mixture to obtain the solder resist ink.
According to one embodiment of the present invention, in the step B1, the temperature of the heating and stirring is 50 to 60 ℃.
According to one embodiment of the present invention, in the step B1, the heating and stirring time is 0.5 to 0.6h.
According to an embodiment of the present invention, in the step B1, the stirring speed of the heating and stirring is 3000-3200r/min.
According to an embodiment of the present invention, after the mixture is obtained in the step B1, the step B further includes an operation of grinding the mixture.
According to one embodiment of the invention, the grinding pressure is 3.5-3.8MPa and the grinding time is 10-15min.
According to an embodiment of the present invention, in the step B2, the method further includes the following steps: a photoinitiator and a curing agent are added to the mixture during the first 20-24 hours of using the solder mask ink to obtain the solder mask ink.
Additional features and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention.
Detailed Description
In the description of the present invention, the description of first, second, etc. is for the purpose of distinguishing between technical features only and should not be construed as indicating or implying a relative importance or implicitly indicating the number of technical features indicated or implicitly indicating the precedence of the technical features indicated.
The words "preferably," "more preferably," and the like in the present invention refer to embodiments of the invention that may provide certain benefits in some instances. However, other embodiments may be preferred under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.
When a range of values is disclosed herein, the range is considered to be continuous and includes both the minimum and maximum values for the range, as well as each value between such minimum and maximum values. Further, when a range refers to an integer, each integer between the minimum and maximum values of the range is included. Further, when multiple range description features or characteristics are provided, the ranges may be combined. In other words, unless otherwise indicated, all ranges disclosed herein are to be understood to include any and all subranges subsumed therein.
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to fall within the scope of the invention.
The reagents, methods and apparatus employed in the present invention, unless otherwise specified, are all conventional in the art.
Example 1
The raw materials of the solder resist ink comprise the following components:
28 parts of bio-based alkali-soluble resin;
28 parts of diallyl type epoxy acrylate resin;
14 parts of diallyl bisphenol A epoxy resin;
9.5 parts of reactive diluent;
2 parts of curing agent;
5.6 parts of photoinitiator;
pigment, 5.6 parts;
6.5 parts of filler;
0.3 parts of dispersing agent;
0.2 part of leveling agent;
And 0.3 parts of defoaming agent.
The reactive diluent is tripropylene glycol diacrylate;
The pigment is phthalocyanine green;
The filler is silicon dioxide;
The dispersing agent is di-gao 1010;
The leveling agent is digao 360;
The defoamer is di-gao 910;
The photoinitiator is 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholino-1-acetone and benzil dimethyl ether;
The curing agent is dicyandiamide.
The preparation method of the bio-based alkali-soluble resin comprises the following steps:
S1, 154 parts of furan methyl glycidyl ether, 72 parts of acrylic acid, 0.2 part of catalyst tetrabutylammonium bromide and 0.01 part of polymerization inhibitor para-hydroxyanisole are added into a reaction vessel, stirring is started, the temperature is raised to 110 ℃, the heat preservation reaction is carried out for 8 hours, and the acrylated furan methyl glycidyl ether is obtained after cooling;
S2, taking 78 parts of propylene glycol methyl ether, starting stirring, introducing N 2,N2 for more than 1 hour, heating to 70 ℃, then dropwise adding 156 parts of propylene glycol methyl ether, 45 parts of the acrylated furan methyl glycidyl ether obtained in the step S1, 10 parts of glycidyl methacrylate, 20 parts of styrene, 25 parts of acrylic acid, 0.8 part of chain transfer agent mercaptopropanol and 0.7 part of initiator azo-diisoheptonitrile mixture, controlling the dropwise adding time to be 2 hours, preserving heat after the dropwise adding is finished, and carrying out polymerization reaction for 4 hours to obtain a mixture;
After the S3 polymerization reaction is finished, increasing the introducing amount of N 2, and heating the mixture to 90 ℃ for continuous reaction for 2 hours to obtain the bio-based alkali-soluble resin; the number average molecular weight of the modified polypropylene is 28300, the molecular weight distribution is 2.46, and the acid value is 194mgKOH/g.
The preparation method of the diallyl type epoxy acrylate resin comprises the following steps:
a1, adding 420 parts of diallyl bisphenol A epoxy resin, 0.14 part of polymerization inhibitor p-hydroxyanisole and 5 parts of catalyst triphenylphosphine into a reaction vessel, starting stirring, and heating to 100 ℃ to obtain a mixture;
A2, dropwise adding 144 parts of acrylic acid into the mixture, wherein the temperature of a reaction system is controlled to be not more than 115 ℃ in the dropwise adding process; after the dripping is finished, heating to 110 ℃ and preserving heat for reaction for 4 hours;
and A3, cooling to obtain the diallyl type epoxy acrylate resin.
The method for preparing the solder resist ink comprises the following steps:
Adding 28 parts of bio-based alkali-soluble resin, 28 parts of diallyl type epoxy acrylate resin, 14 parts of diallyl bisphenol A epoxy resin, 9.5 parts of tripropylene glycol diacrylate as an active diluent, 5.6 parts of pigment phthalocyanine green, 6.5 parts of filler silicon dioxide, 0.3 part of dispersing agent di-high 1010, 0.2 part of leveling agent di-high 360 and 0.3 part of defoaming agent di-high 910 into a dispersing container, and starting high-speed mechanical stirring to obtain a mixture, wherein the temperature is 50 ℃ and the stirring speed is 3000r/min and the stirring time is 0.5h in the stirring process;
b2, grinding the mixture obtained in the step B1 on a grinder, wherein the grinding pressure is 3.5MPa, and the grinding time is 10min, so as to obtain a ground material;
3.7 parts of photoinitiator 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinyl-1-acetone, 1.9 parts of photoinitiator benzil dimethyl ether and 2.0 parts of curing agent dicyandiamide are added into the ground material within 20 hours before the use, and stirring is continued for 30 minutes until the components are uniformly dissolved, so that the solder resist ink is obtained.
Example 2
The raw materials of the solder resist ink comprise the following components:
30 parts of bio-based alkali-soluble resin;
21 parts of diallyl type epoxy acrylate resin;
17 parts of diallyl bisphenol A epoxy resin;
8.5 parts of reactive diluent;
3.4 parts of curing agent;
4.3 parts of photoinitiator;
4.6 parts of pigment;
10 parts of filler;
0.6 parts of dispersing agent;
0.3 part of leveling agent;
And 0.3 parts of defoaming agent.
The reactive diluent is trimethylolpropane triacrylate;
The pigment is phthalocyanine blue;
The filler is silicon dioxide;
The dispersing agent is di-gao 1010;
the leveling agent is di-gao 607;
the defoamer is digao 921;
The photoinitiator is 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholino-1-acetone and 2, 4-diethyl thioxanthone;
The curing agent is methylated melamine.
The preparation method of the bio-based alkali-soluble resin comprises the following steps:
S1, 154 parts of furan methyl glycidyl ether, 72 parts of acrylic acid, 0.4 part of catalyst tetrabutylammonium bromide and 0.03 part of polymerization inhibitor p-hydroxyanisole are added into a reaction vessel, stirring is started, the temperature is raised to 110 ℃, the heat preservation reaction is carried out for 7 hours, and the acrylated furan methyl glycidyl ether is obtained after cooling;
S2, taking 63 parts of propylene glycol methyl ether, starting stirring, introducing N 2,N2 for more than 1 hour, heating to 70 ℃, then dropwise adding a mixture of 126 parts of propylene glycol methyl ether, 40 parts of the acrylated furan methyl glycidyl ether obtained in the step S1, 15 parts of glycidyl methacrylate, 20 parts of styrene, 25 parts of acrylic acid, 1 part of chain transfer agent mercaptopropanol and 1 part of initiator azo-diisoheptonitrile, controlling the dropwise adding time to be 2 hours, preserving heat after the dropwise adding is finished, and carrying out polymerization reaction for 4 hours to obtain a mixture;
After the S3 polymerization reaction is finished, increasing the introducing amount of N 2, and heating the mixture to 90 ℃ for continuous reaction for 2 hours to obtain the bio-based alkali-soluble resin; the number average molecular weight of the modified polypropylene is 26100, the molecular weight distribution is 2.32, and the acid value is 194.4mgKOH/g.
The preparation method of the diallyl type epoxy acrylate resin comprises the following steps:
A1, adding 420 parts of diallyl bisphenol A epoxy resin, 0.12 part of polymerization inhibitor p-hydroxyanisole and 4.4 parts of catalyst triphenylphosphine into a reaction vessel, starting stirring, and heating to 100 ℃ to obtain a mixture;
A2, dropwise adding 144 parts of acrylic acid into the mixture, wherein the temperature of a reaction system is controlled to be not more than 115 ℃ in the dropwise adding process; after the dripping is finished, heating to 110 ℃ and preserving heat for reaction for 4 hours;
and A3, cooling to obtain the diallyl type epoxy acrylate resin.
The method for preparing the solder resist ink comprises the following steps:
B1, adding 30 parts of bio-based alkali-soluble resin, 21 parts of diallyl type epoxy acrylate resin, 17 parts of diallyl bisphenol A epoxy resin, 8.5 parts of trimethylolpropane triacrylate as an active diluent, 4.6 parts of pigment phthalocyanine blue, 10 parts of filler silicon dioxide, 0.6 part of dispersing agent di-high 1010, 0.3 part of leveling agent di-high 607 and 0.3 part of defoaming agent di-high 921 into a dispersing container, and starting high-speed mechanical stirring to obtain a mixture, wherein the temperature is 50 ℃ and the stirring speed is 3000r/min, and the stirring time is 0.5h;
b2, grinding the mixture obtained in the step B1 on a grinder, wherein the grinding pressure is 3.5MPa, and the grinding time is 10min, so as to obtain a ground material;
And B3, adding 1.7 parts of photoinitiator 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinyl-1-acetone, 2.6 parts of photoinitiator 2, 4-diethyl thioxanthone and 3.4 parts of curing agent methylated melamine into the ground product within 20 hours before using, and continuously stirring for 30 minutes until the components are uniformly dissolved, thus obtaining the solder resist ink.
Example 3
The raw materials of the solder resist ink comprise the following components:
34 parts of bio-based alkali-soluble resin;
28 parts of diallyl type epoxy acrylate resin;
Bisphenol a epoxy resin, 9 parts;
5 parts of reactive diluent;
4.7 parts of curing agent;
5.7 parts of photoinitiator;
3 parts of pigment;
9.5 parts of filler;
0.4 parts of dispersing agent;
0.3 part of leveling agent;
0.4 parts of defoaming agent.
The reactive diluent is trimethylolpropane triacrylate;
The pigment is phthalocyanine green;
The filler is silicon dioxide;
The dispersing agent is 650 d;
The leveling agent is digao 360;
The defoamer is di-gao 944;
the photoinitiator is 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone and benzil dimethyl ether;
The curing agent is methylated melamine.
The preparation method of the bio-based alkali-soluble resin comprises the following steps:
S1, adding 154 parts of furan methyl glycidyl ether, 72 parts of acrylic acid, 0.6 part of catalyst tetrabutylammonium bromide and 0.02 part of polymerization inhibitor para-hydroxyanisole into a reaction container, starting stirring, heating to 110 ℃, preserving heat for reaction for 6 hours, and cooling to obtain acrylic acid ester furan methyl glycidyl ether;
S2, taking 63 parts of propylene glycol methyl ether, starting stirring, introducing N 2,N2 for more than 1 hour, heating to 70 ℃, then dropwise adding a mixture of 126 parts of propylene glycol methyl ether, 35 parts of the acrylated furan methyl glycidyl ether obtained in the step S1, 20 parts of glycidyl methacrylate, 15 parts of styrene, 30 parts of acrylic acid, 0.6 part of chain transfer agent mercaptopropanol and 1.3 parts of initiator azo-diisoheptonitrile, controlling the dropwise adding time to be 2 hours, and carrying out thermal insulation polymerization for 4 hours after the dropwise adding is finished to obtain a mixture;
After the S3 polymerization reaction is finished, increasing the introducing amount of N 2, and heating the mixture to 90 ℃ for continuous reaction for 2 hours to obtain the bio-based alkali-soluble resin; the number average molecular weight of the modified polypropylene resin is 24300, the molecular weight distribution is 2.68, and the acid value is 233.3mgKOH/g.
The preparation method of the diallyl type epoxy acrylate resin comprises the following steps:
A1, adding 420 parts of diallyl bisphenol A epoxy resin, 0.07 part of polymerization inhibitor p-hydroxyanisole and 2.3 parts of catalyst triphenylphosphine into a reaction vessel, starting stirring, and heating to 110 ℃ to obtain a mixture;
a2, 135 parts of acrylic acid is dripped into the mixture, and the temperature of a reaction system is controlled to be not more than 115 ℃ in the dripping process; after the dripping is finished, heating to 115 ℃ and preserving heat for reaction for 4 hours;
and A3, cooling to obtain the diallyl type epoxy acrylate resin.
The method for preparing the solder resist ink comprises the following steps:
Adding 34 parts of bio-based alkali-soluble resin, 28 parts of diallyl type epoxy acrylate resin, 9 parts of bisphenol A epoxy resin, 5 parts of trimethylolpropane triacrylate serving as an active diluent, 3 parts of pigment phthalocyanine green, 9.5 parts of filler silicon dioxide, 0.4 part of dispersing agent di-height 650, 0.3 part of leveling agent di-height 360 and 0.4 part of defoaming agent di-height 944 into a dispersing container, and starting high-speed mechanical stirring to obtain a mixture, wherein the temperature is 50 ℃ and the stirring speed is 3000r/min, and the stirring time is 0.5h;
b2, grinding the mixture obtained in the step B1 on a grinder, wherein the grinding pressure is 3.5MPa, and the grinding time is 10min, so as to obtain a ground material;
3, 3.8 parts of photoinitiator 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, 1.9 parts of photoinitiator benzil dimethyl ether and 4.7 parts of curing agent methylated melamine are added into the ground product within 20 hours before the use, and stirring is continued for 30 minutes until the components are uniformly dissolved, so as to obtain the solder resist ink.
Example 4
The raw materials of the solder resist ink comprise the following components:
20 parts of bio-based alkali-soluble resin;
33 parts of diallyl type epoxy acrylate resin;
9 parts of phenolic epoxy resin;
14 parts of a reactive diluent;
4.7 parts of curing agent;
6.6 parts of photoinitiator;
3.9 parts of pigment;
8 parts of filler;
0.3 parts of dispersing agent;
0.3 part of leveling agent;
and 0.2 parts of defoaming agent.
The reactive diluent is trimethylolpropane triacrylate;
the pigment is benzidine yellow;
the filler is talcum powder;
the dispersant is di-gao 671;
the leveling agent is digao 960;
The defoamer is di-high 963;
the photoinitiator is 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone and 2, 4-diethyl thioxanthone;
The curing agent is dicyandiamide.
The preparation method of the bio-based alkali-soluble resin comprises the following steps:
S1, adding 154 parts of furan methyl glycidyl ether, 72 parts of acrylic acid, 0.4 part of catalyst tetrabutylammonium bromide and 0.04 part of polymerization inhibitor p-hydroxyanisole into a reaction container, starting stirring, heating to 110 ℃, preserving heat for reaction for 8 hours, and cooling to obtain acrylic acid ester furan methyl glycidyl ether;
S2, taking 51 parts of propylene glycol methyl ether, starting stirring, introducing N 2,N2 for more than 1 hour, heating to 70 ℃, then dropwise adding 102 parts of propylene glycol methyl ether, 45 parts of the acrylated furan methyl glycidyl ether obtained in the step S1, 10 parts of glycidyl methacrylate, 25 parts of styrene, 20 parts of acrylic acid, 0.2 part of chain transfer agent mercaptopropanol and 1.5 parts of initiator azo-diisoheptonitrile mixture, controlling the dropwise adding time to be 3 hours, and carrying out thermal insulation polymerization reaction for 3 hours after the dropwise adding is finished to obtain a mixture;
after the S3 polymerization reaction is finished, increasing the introducing amount of N 2, and heating the mixture to 90 ℃ for continuous reaction for 2 hours to obtain the bio-based alkali-soluble resin; the number average molecular weight of the modified polypropylene resin is 22500, the molecular weight distribution is 2.91, and the acid value is 155mgKOH/g.
The preparation method of the diallyl type epoxy acrylate resin comprises the following steps:
A1, adding 420 parts of diallyl bisphenol A epoxy resin, 0.09 part of polymerization inhibitor p-hydroxyanisole and 3.5 parts of catalyst triphenylphosphine into a reaction vessel, starting stirring, and heating to 100 ℃ to obtain a mixture;
a2, 1138 parts of acrylic acid is dropwise added into the mixture, and the temperature of a reaction system is controlled to be not more than 115 ℃ in the dropwise adding process; after the dripping is finished, heating to 110 ℃ and preserving heat for reaction for 4 hours;
and A3, cooling to obtain the diallyl type epoxy acrylate resin.
The method for preparing the solder resist ink comprises the following steps:
B1, adding 20 parts of bio-based alkali-soluble resin, 33 parts of diallyl type epoxy acrylate resin, 9 parts of phenolic epoxy resin, 14 parts of trimethylolpropane triacrylate as an active diluent, 3.9 parts of pigment benzidine yellow, 8 parts of filler talcum powder, 0.3 part of dispersing agent di-high 671, 0.3 part of leveling agent di-high 960 and 0.2 part of defoaming agent di-high 963 into a dispersing container, and starting high-speed mechanical stirring to obtain a mixture, wherein the temperature is 50 ℃ and the stirring speed is 3000r/min, and the stirring time is 0.5h;
b2, grinding the mixture obtained in the step B1 on a grinder, wherein the grinding pressure is 3.5MPa, and the grinding time is 10min, so as to obtain a ground material;
3.8 parts of photoinitiator 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, 2.8 parts of photoinitiator 2, 4-diethyl thioxanthone and 4.7 parts of curing agent dicyandiamide are added into the ground material within 20 hours before the use, and stirring is continued for 30 minutes until the components are uniformly dissolved, so that the solder resist ink is obtained.
Example 5
The raw materials of the solder resist ink comprise the following components:
27 parts of bio-based alkali-soluble resin;
30 parts of diallyl type epoxy acrylate resin;
10 parts of diallyl bisphenol A epoxy resin;
7 parts of reactive diluent;
4.4 parts of curing agent;
6 parts of photoinitiator;
Pigment, 5.3 parts;
9.2 parts of filler;
0.5 parts of dispersing agent;
0.2 part of leveling agent;
0.4 parts of defoaming agent.
The reactive diluent is dipentaerythritol hexaacrylate;
The pigment is permanent violet;
The filler is barium sulfate;
the dispersant is di gao 681;
the leveling agent is Digao 980;
the defoamer is digao 971;
the photoinitiator is 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholino-1-acetone and diphenyl ketone;
The curing agent is benzoguanide.
The preparation method of the bio-based alkali-soluble resin comprises the following steps:
S1, adding 154 parts of furan methyl glycidyl ether, 72 parts of acrylic acid, 0.5 part of catalyst tetrabutylammonium bromide and 0.03 part of polymerization inhibitor para-hydroxyanisole into a reaction container, starting stirring, heating to 110 ℃, preserving heat for reaction for 7 hours, and cooling to obtain acrylic acid ester furan methyl glycidyl ether;
s2, taking 51 parts of propylene glycol methyl ether, starting stirring, introducing N 2,N2 for more than 1 hour, heating to 70 ℃, then dropwise adding a mixture of 102 parts of propylene glycol methyl ether, 40 parts of the acrylated furan methyl glycidyl ether obtained in the step S1, 20 parts of glycidyl methacrylate, 15 parts of styrene, 25 parts of acrylic acid, 0.5 part of chain transfer agent mercaptopropanol and 1.2 parts of initiator azo-diisoheptonitrile, controlling the dropwise adding time to be 2 hours, and carrying out thermal insulation polymerization for 4 hours after the dropwise adding is finished to obtain a mixture;
After the S3 polymerization reaction is finished, increasing the introducing amount of N 2, and heating the mixture to 90 ℃ for continuous reaction for 2 hours to obtain the bio-based alkali-soluble resin; the number average molecular weight of the modified polypropylene is 24800, the molecular weight distribution is 2.77, and the acid value is 194.2mgKOH/g.
The preparation method of the diallyl type epoxy acrylate resin comprises the following steps:
A1, adding 420 parts of diallyl bisphenol A epoxy resin, 0.09 part of polymerization inhibitor p-hydroxyanisole and 3 parts of catalyst triphenylphosphine into a reaction vessel, starting stirring, and heating to 100 ℃ to obtain a mixture;
a2, dropwise adding 138 parts of acrylic acid into the mixture, wherein the temperature of a reaction system is controlled to be not more than 115 ℃ in the dropwise adding process; after the dripping is finished, heating to 115 ℃ and preserving heat for reaction for 4 hours;
and A3, cooling to obtain the diallyl type epoxy acrylate resin.
The method for preparing the solder resist ink comprises the following steps:
Adding 27 parts of bio-based alkali-soluble resin, 30 parts of diallyl type epoxy acrylate resin, 10 parts of diallyl bisphenol A epoxy resin, 7 parts of dipentaerythritol hexaacrylate serving as an active diluent, 5.3 parts of pigment permanent violet, 9.2 parts of filler barium sulfate, 0.5 part of dispersing agent digao 681, 0.2 part of leveling agent digao 980 and 0.4 part of defoaming agent digao 971 into a dispersing container, and starting high-speed mechanical stirring to obtain a mixture, wherein the temperature is 50 ℃ and the stirring speed is 3000r/min and the stirring time is 0.5h in the stirring process;
b2, grinding the mixture obtained in the step B1 on a grinder, wherein the grinding pressure is 3.5MPa, and the grinding time is 10min, so as to obtain a ground material;
and B3, adding 4 parts of photoinitiator 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholino-1-acetone, 2 parts of photoinitiator diphenyl ketone and 4.4 parts of curing agent benzoguanamine into the ground material within 20 hours before use, and continuously stirring for 30 minutes until the components are uniformly dissolved to obtain the solder resist ink.
Comparative example 1
The diallyl type epoxy acrylate resin prepared in the invention is not added in the formulation of comparative example 1.
The raw materials of the solder resist ink comprise the following components:
37 parts of bio-based alkali-soluble resin;
23 parts of diallyl bisphenol A epoxy resin;
19.5 parts of a reactive diluent;
2 parts of curing agent;
5.6 parts of photoinitiator;
6.5 parts of pigment;
6.5 parts of filler;
0.3 parts of dispersing agent;
0.2 part of leveling agent;
And 0.3 parts of defoaming agent.
The reactive diluent is tripropylene glycol diacrylate;
The pigment is phthalocyanine green;
The filler is silicon dioxide;
The dispersing agent is di-gao 1010;
The leveling agent is digao 360;
The defoamer is di-gao 910;
The photoinitiator is 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholino-1-acetone and benzil dimethyl ether;
The curing agent is dicyandiamide.
The preparation method of the bio-based alkali-soluble resin comprises the following steps:
S1, 154 parts of furan methyl glycidyl ether, 72 parts of acrylic acid, 0.2 part of catalyst tetrabutylammonium bromide and 0.01 part of polymerization inhibitor para-hydroxyanisole are added into a reaction vessel, stirring is started, the temperature is raised to 110 ℃, the heat preservation reaction is carried out for 8 hours, and the acrylated furan methyl glycidyl ether is obtained after cooling;
S2, taking 78 parts of propylene glycol methyl ether, starting stirring, introducing N 2,N2 for more than 1 hour, heating to 70 ℃, then dropwise adding 156 parts of propylene glycol methyl ether, 45 parts of the acrylated furan methyl glycidyl ether obtained in the step S1, 10 parts of glycidyl methacrylate, 20 parts of styrene, 25 parts of acrylic acid, 0.8 part of chain transfer agent mercaptopropanol and 0.7 part of initiator azo-diisoheptonitrile mixture, controlling the dropwise adding time to be 2 hours, preserving heat after the dropwise adding is finished, and carrying out polymerization reaction for 4 hours to obtain a mixture;
After the S3 polymerization reaction is finished, increasing the introducing amount of N 2, and heating the mixture to 90 ℃ for continuous reaction for 2 hours to obtain the bio-based alkali-soluble resin; the number average molecular weight of the modified polypropylene is 28300, the molecular weight distribution is 2.46, and the acid value is 194mgKOH/g.
The method for preparing the solder resist ink comprises the following steps:
B1, adding 37 parts of bio-based alkali-soluble resin, 23 parts of diallyl bisphenol A epoxy resin, 19.5 parts of tripropylene glycol diacrylate as a reactive diluent, 5.6 parts of pigment phthalocyanine green, 6.5 parts of filler silicon dioxide, 0.3 part of dispersing agent diGao 1010, 0.2 part of leveling agent diGao 360 and 0.3 part of defoaming agent diGao 910 into a dispersing container, and starting high-speed mechanical stirring for 0.5h;
b2, grinding the mixture obtained in the step B1 on a grinder, wherein the grinding pressure is 3.5MPa, and the grinding time is 10min, so as to obtain a ground material;
3.7 parts of photoinitiator 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinyl-1-acetone, 1.9 parts of photoinitiator benzil dimethyl ether and 2.0 parts of curing agent dicyandiamide are added into the ground material within 20 hours before the use, and stirring is continued for 30 minutes until the components are uniformly dissolved, so that the solder resist ink is obtained.
Comparative example 2
Comparative example 2 the formulation was not supplemented with the alkaloid soluble resin prepared in the invention.
The raw materials of the solder resist ink comprise the following components:
37 parts of diallyl type epoxy acrylate resin;
23 parts of diallyl bisphenol A epoxy resin;
19.5 parts of a reactive diluent;
2 parts of curing agent;
5.6 parts of photoinitiator;
pigment, 5.6 parts;
6.5 parts of filler;
0.3 parts of dispersing agent;
0.2 part of leveling agent;
And 0.3 parts of defoaming agent.
The reactive diluent is tripropylene glycol diacrylate;
The pigment is phthalocyanine green;
The filler is silicon dioxide;
The dispersing agent is di-gao 1010;
The leveling agent is digao 360;
The defoamer is di-gao 910;
The photoinitiator is 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholino-1-acetone and benzil dimethyl ether;
The curing agent is dicyandiamide.
The preparation method of the diallyl type epoxy acrylate resin comprises the following steps:
a1, adding 420 parts of diallyl bisphenol A epoxy resin, 0.14 part of polymerization inhibitor p-hydroxyanisole and 5 parts of catalyst triphenylphosphine into a reaction vessel, starting stirring, and heating to 100 ℃ to obtain a mixture;
A2, dropwise adding 144 parts of acrylic acid into the mixture, wherein the temperature of a reaction system is controlled to be not more than 115 ℃ in the dropwise adding process; after the dripping is finished, heating to 110 ℃ and preserving heat for reaction for 4 hours;
and A3, cooling to obtain the diallyl type epoxy acrylate resin.
The method for preparing the solder resist ink comprises the following steps:
B1, adding 37 parts of diallyl type epoxy acrylate resin, 23 parts of diallyl bisphenol A epoxy resin, 19.5 parts of tripropylene glycol diacrylate as a reactive diluent, 5.6 parts of pigment phthalocyanine green, 6.5 parts of filler silicon dioxide, 0.3 part of dispersing agent digao 1010, 0.2 part of leveling agent digao 360 and 0.3 part of defoaming agent digao 910 into a dispersing container, and starting high-speed mechanical stirring to obtain a mixture, wherein the temperature is 50 ℃, the stirring speed is 3000r/min, and the stirring time is 0.5h;
b2, grinding the mixture obtained in the step B1 on a grinder, wherein the grinding pressure is 3.5MPa, and the grinding time is 10min, so as to obtain a ground material;
3.7 parts of photoinitiator 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinyl-1-acetone, 1.9 parts of photoinitiator benzil dimethyl ether and 2.0 parts of curing agent dicyandiamide are added into the ground material within 20 hours before the use, and stirring is continued for 30 minutes until the components are uniformly dissolved, so that the solder resist ink is obtained.
Performance test:
The solder resist ink obtained in examples 1 to 5 and comparative examples 1 to 2 was screen-printed with 120 mesh, and subjected to a pre-bake (70 to 75 ℃ C./30 to 50 min), an exposure (600 to 750mj/cm 2), a development (1 wt% Na 2CO3 aqueous solution, 30.+ -. 2 ℃ C., 1.0 to 3.0kg/cm 2 spray pressure, 50 to 80 s), a post-hardening (145 to 155 ℃ C./50 to 70 min) and the like in this order. Adhesion testing was performed according to ASTM D3359, hardness testing was performed according to ASTM D3363, dielectric properties were performed according to IPC TM-650 5.5.3.7-1998 in the electronic interconnect industry standard (American society for printed circuit industry), and the main performance test results are shown in Table 1.
TABLE 1
As can be seen from table 1: compared with the example, the diallyl type epoxy acrylate resin prepared in the invention is not added in the formula of the comparative example 1, so that the crosslinking degree of the solder resist ink is reduced after curing, and the heat resistance, resolution and dielectric property of the cured film are obviously deteriorated; compared with the example, the formula of the comparative example 2 is not added with the bio-based alkali soluble resin prepared in the invention, and the alkali soluble structure of the solder resist ink system is lost, so that the cured film cannot be effectively developed; the combination of properties exhibited by example 1 is optimal.
In view of the above, the bio-based low dielectric solder resist ink prepared by taking the bio-based alkali-soluble resin and the diallyl epoxy acrylate resin prepared by the invention as matrix resins has excellent adhesive force, heat resistance, low dielectric constant and low loss factor, and has wide application and market prospect.
The foregoing is merely exemplary embodiments of the present invention and are not intended to limit the scope of the present invention, and all equivalent modifications made by the present invention or direct or indirect application in the relevant art are intended to be included in the scope of the present invention.
Claims (10)
1. A solder resist ink, characterized in that: the raw materials of the solder resist ink comprise the following components:
A bio-based alkali-soluble resin;
an epoxy resin containing at least a diallyl type epoxy acrylate resin;
A curing agent;
A photoinitiator;
a filler;
An auxiliary agent;
the structural formula of the bio-based alkali-soluble resin is as follows:
wherein x, y, z and m > 0;
The structural formula of the diallyl epoxy acrylate resin is as follows:
2. A solder resist ink as defined in claim 1, wherein: the raw materials of the solder resist ink comprise the following components in parts by weight:
10-40 parts of bio-based alkali-soluble resin;
15-60 parts of epoxy resin; the epoxy resin at least contains 10-40 parts of diallyl type epoxy acrylate resin;
2-6 parts of curing agent;
3-10 parts of photoinitiator;
5-15 parts of filler;
And 7-31 parts of auxiliary agent.
3. A solder resist ink as defined in claim 1, wherein: the epoxy resin also comprises at least one of bisphenol A epoxy resin, bisphenol F epoxy resin, diallyl bisphenol A epoxy resin and phenolic epoxy resin.
4. A solder resist ink as defined in claim 1, wherein: the photoinitiator comprises at least one of 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinyl-1-propanone, benzil dimethyl ether, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, benzophenone and 2, 4-diethyl thioxanthone.
5. A solder resist ink as defined in claim 1, wherein: the preparation method of the bio-based alkali-soluble resin comprises the following steps:
S1, mixing furan methyl glycidyl ether, acrylic acid, a catalyst and a polymerization inhibitor, and cooling after heating reaction to obtain acrylic acid ester furan methyl glycidyl ether;
S2, introducing protective atmosphere into a reaction container, heating, adding propylene glycol methyl ether, the acrylated furan methyl glycidyl ether obtained in the step S1, glycidyl methacrylate, styrene, acrylic acid, a chain transfer agent and an initiator, preserving heat after the addition, and carrying out polymerization reaction to obtain a mixture;
And S3, after the polymerization reaction in the step S2 is finished, heating the mixture for reaction to obtain the bio-based alkali-soluble resin.
6. A solder resist ink as defined in claim 5, wherein: in step S1, the catalyst comprises tetrabutylammonium bromide.
7. A solder resist ink as defined in claim 5, wherein: in step S1, the polymerization inhibitor includes para-hydroxyanisole.
8. A solder resist ink as defined in claim 5, wherein: the ratio of the temperature after temperature rise in the step S2 to the temperature after temperature rise in the step S3 is 70-80℃:90-100 ℃.
9. A solder resist ink as defined in claim 1, wherein: the preparation method of the diallyl type epoxy acrylate resin comprises the following steps:
A1, mixing diallyl bisphenol A epoxy resin, a polymerization inhibitor p-hydroxyanisole and a catalyst triphenylphosphine, and heating to react to obtain a mixture;
a2, controlling the temperature of a reaction system to be not more than 115 ℃, adding acrylic acid into the mixture, and then heating to react to obtain the diallyl type epoxy acrylate resin.
10. A method of preparing a solder resist ink as claimed in any one of claims 1 to 9, characterized in that: the method comprises the following steps:
b1, mixing the bio-based alkali-soluble resin, the epoxy resin and the filler in a container, heating and stirring to obtain a mixture;
And B2, adding a photoinitiator and a curing agent into the mixture to obtain the solder resist ink.
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