CN109160997B - Alkali solubility UV-cured resin, preparation method containing urethano and the ultraviolet light solidification etch-resistant material containing it - Google Patents
Alkali solubility UV-cured resin, preparation method containing urethano and the ultraviolet light solidification etch-resistant material containing it Download PDFInfo
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- CN109160997B CN109160997B CN201810985106.XA CN201810985106A CN109160997B CN 109160997 B CN109160997 B CN 109160997B CN 201810985106 A CN201810985106 A CN 201810985106A CN 109160997 B CN109160997 B CN 109160997B
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- China
- Prior art keywords
- cured resin
- alkali solubility
- urethano
- anhydride
- diisocyanate
- Prior art date
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- 239000011347 resin Substances 0.000 title claims abstract description 93
- 229920005989 resin Polymers 0.000 title claims abstract description 93
- 239000003513 alkali Substances 0.000 title claims abstract description 78
- 239000000463 material Substances 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 238000007711 solidification Methods 0.000 title claims description 26
- 230000008023 solidification Effects 0.000 title claims description 26
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 18
- 239000002243 precursor Substances 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 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 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 13
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims abstract description 10
- 239000012975 dibutyltin dilaurate Substances 0.000 claims abstract description 10
- 150000007524 organic acids Chemical class 0.000 claims abstract description 10
- -1 dimethacrylate Chemical compound 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 21
- 238000005530 etching Methods 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 150000008064 anhydrides Chemical group 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 150000005846 sugar alcohols Polymers 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 6
- 229940091853 isobornyl acrylate Drugs 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- 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 3
- MGVBVRJCXZHQDI-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanoate;carbamimidoylazanium Chemical compound NC([NH3+])=N.[O-]C(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 MGVBVRJCXZHQDI-UHFFFAOYSA-N 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 3
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- APZPSKFMSWZPKL-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)CO APZPSKFMSWZPKL-UHFFFAOYSA-N 0.000 claims description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 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 claims description 3
- 150000002334 glycols Chemical class 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- 229940117969 neopentyl glycol Drugs 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
- 229940113120 dipropylene glycol Drugs 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims 1
- LTQUNXZZRXILFZ-UHFFFAOYSA-N 4-(2-ethoxyethoxy)-2-methylidenebutanoic acid Chemical compound CCOCCOCCC(=C)C(O)=O LTQUNXZZRXILFZ-UHFFFAOYSA-N 0.000 claims 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 claims 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims 1
- WTNMMKJWWSEFNO-UHFFFAOYSA-N CC(C)[S] Chemical compound CC(C)[S] WTNMMKJWWSEFNO-UHFFFAOYSA-N 0.000 claims 1
- AIJOSEUGNIGKHG-UHFFFAOYSA-N CCO[N+]#[C-] Chemical class CCO[N+]#[C-] AIJOSEUGNIGKHG-UHFFFAOYSA-N 0.000 claims 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 claims 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229940119545 isobornyl methacrylate Drugs 0.000 claims 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 claims 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 35
- 239000007788 liquid Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000003973 paint Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 5
- 229940113165 trimethylolpropane Drugs 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001816 cooling Methods 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
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 238000004065 wastewater treatment Methods 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- GNEPLYVYORHREW-UHFFFAOYSA-N 1,1,3,3,6-pentamethyl-7-nitro-2h-inden-5-amine Chemical compound CC1=C(N)C=C2C(C)(C)CC(C)(C)C2=C1[N+]([O-])=O GNEPLYVYORHREW-UHFFFAOYSA-N 0.000 description 2
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 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
- 238000002474 experimental method Methods 0.000 description 2
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
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- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
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- ZXAGXLDEMUNQSH-UHFFFAOYSA-N 2-ethylanthracene Chemical compound C1=CC=CC2=CC3=CC(CC)=CC=C3C=C21 ZXAGXLDEMUNQSH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- WRFMXTSFJSLZSW-UHFFFAOYSA-N C(C)OC(C(C(O)OCC)(C)C)O Chemical compound C(C)OC(C(C(O)OCC)(C)C)O WRFMXTSFJSLZSW-UHFFFAOYSA-N 0.000 description 1
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- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WXLFIFHRGFOVCD-UHFFFAOYSA-L azophloxine Chemical compound [Na+].[Na+].OC1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 WXLFIFHRGFOVCD-UHFFFAOYSA-L 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 239000006229 carbon black Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- XFCMNSHQOZQILR-UHFFFAOYSA-N diethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- VMWUNHCDOIDVAA-UHFFFAOYSA-N isocyanatooxyethane Chemical class CCON=C=O VMWUNHCDOIDVAA-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 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
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 235000012739 red 2G Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000011863 silicon-based powder 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
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/20—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for coatings strippable as coherent films, e.g. temporary coatings strippable as coherent films
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- Polymerisation Methods In General (AREA)
Abstract
The present invention relates to a kind of, and alkali solubility UV-cured resin, preparation method and the ultraviolet light containing it containing urethano solidify etch-resistant material.The preparation method of alkali solubility UV-cured resin containing urethano is that diisocyanate and dibutyl tin dilaurate are added separately in the not acrylate monomer of hydroxyl, then pentaerythritol triacrylate is added and prepares half addition product of diisocyanate, half addition product of diisocyanate is added to alkali solubility UV-cured resin precursor of the polyols preparation containing urethano again, then organic acid anhydride is added in the alkali solubility UV-cured resin precursor containing urethano and prepares the alkali solubility UV-cured resin containing urethano.The preparation process of the above-mentioned alkali solubility UV-cured resin containing urethano is simple.
Description
Technical field
The present invention relates to light-cured resin fields, solidify tree more particularly to a kind of alkali solubility ultraviolet light containing urethano
Rouge, preparation method and the ultraviolet light containing it solidify etch-resistant material.
Background technique
Printed circuit board (PCB) is the base components of hyundai electronics industry, can largely use ultraviolet light in manufacturing process
Curing anti-etching material.Ultraviolet light is solidified etch-resistant material and is coated in copper-clad plate by the silk screen by being printed on required pattern, warp
The copper face that do not protected by etch-resistant material is etched away with etching solution, then uses sodium hydrate aqueous solution by UV machine curing of coating
Remove the etch-resistant material on surface as film liquid is taken off to get to the printed circuit board for making route.
Ultraviolet light, which is solidified the film formed after etch-resistant material solidifies and is dissolved in or is dispersed in fractionlet shape, to be taken off in film liquid,
The using effect for taking off film liquid can be reduced, the use time for taking off film liquid is shortened, to increase the dosage and wastewater treatment for taking off film liquid
Cost.In order to extend the dosage and cost for wastewater treatment for taking off film liquid using time, reduction for taking off film liquid, can generally add after taking off film
Film gatherer collects the film taken off, and reduces film entrance to the greatest extent and takes off in film liquid.Traditional ultraviolet light curing anti-etching material
After material takes off film with NaOH aqueous solution, it is readily soluble in or is dispersed in fractionlet shape and taken off in film liquid, lead to film gatherer winder efficiency
It is lower, increase the dosage and cost for wastewater treatment for taking off film liquid.
Summary of the invention
It is taken off for traditional ultraviolet light solidification etch-resistant material and is readily soluble in membrane process or is dispersed in fractionlet shape
The problems in film liquid is taken off, provides a kind of alkali solubility UV-cured resin containing urethano, preparation method and containing the ultraviolet of its
Photocureable etching-resistant material.
The preparation method of the present invention provides a kind of alkali solubility UV-cured resin containing urethano, the preparation method
The following steps are included:
Diisocyanate and dibutyl tin dilaurate are added separately in the not acrylate monomer of hydroxyl, then
Pentaerythritol triacrylate is added and obtains the first reaction system, is kept for 40 DEG C -70 DEG C of reaction temperature, monitors the first reaction system
Middle diisocyanate-changes of contents of NCO group, when the content of described-NCO group is the 48%-55% of initial content
Stop reaction, obtains half addition product of diisocyanate；
Half addition product of diisocyanate is added in polyalcohol and obtains the second reaction system, holding reaction temperature is
40 DEG C -80 DEG C, when in the second reaction system-content of NCO group be 0 when stop reaction to get arriving the alkali solubility containing urethano
UV-cured resin precursor；
Organic acid anhydride is added in the alkali solubility UV-cured resin precursor containing urethano and obtains third reaction
System, keeping reaction temperature is 60 DEG C -90 DEG C, is stopped when the acid value in third reaction system is 60mgKOH/g-120mgKOH/g
It only reacts to get the alkali solubility UV-cured resin containing urethano is arrived.
The preparation process of the above-mentioned alkali solubility UV-cured resin containing urethano is simple, and the alkali containing urethano is prepared
Urethano is introduced in the strand of dissolubility UV-cured resin, and then is enhanced the flexibility of UV-cured resin and glued
Attached property.In addition, introducing multiple acrylate groups in above-mentioned resin structure, crosslink density is increased, film is strong after solidification
Degree is further increased.Furthermore the above-mentioned alkali solubility UV-cured resin containing urethano contains carboxyl, there is alkali soluble
Property.
The molar ratio of the pentaerythritol triacrylate and the diisocyanate is 1 in one of the embodiments:
(1-1.05)；The mass ratio of the diisocyanate and the dibutyl tin dilaurate is 100:(0.1-1)；Two isocyanide
The mass ratio of the acrylate monomer of acid esters and the not hydroxyl is 1:(0.1-0.3)；Half addition product of diisocyanate
Molar ratio with polyalcohol is 1:(1-1.05)；Anhydride group and the alkali solubility containing urethano in the organic acid anhydride is purple
The molar ratio of hydroxyl in outer photocurable resin precursor is (0.5-1): 1.
The diisocyanate is methyl diphenylene diisocyanate, toluene diisocynate in one of the embodiments,
One of ester, isophorone diisocyanate and hexamethylene diisocyanate are a variety of.
The acrylate monomer of the not hydroxyl is isobornyl acrylate, methyl-prop in one of the embodiments,
Olefin(e) acid isobornyl thiocyanoacetate, ethoxyethoxyethyl acrylate, 2- phenoxyethyl acrylate, diethylene glycol dimethyl allene
Acid esters, tripropylene glycol diacrylate, dipropylene glycol diacrylate, neopentylglycol diacrylate, 1,6-HD dipropyl
Olefin(e) acid ester, trimethylolpropane trimethacrylate, trimethylol-propane trimethacrylate and ethyoxyl trimethylolpropane
One of triacrylate is a variety of.
In one of the embodiments, the polyalcohol be polyethylene glycol, ethylene glycol, 1,2-PD, 1,4-butanediol,
In 1,6-HD, neopentyl glycol, dipropylene glycol, polyether Glycols, polyester diol, trimethylolpropane and glycerol
It is one or more.
The organic acid anhydride is maleic anhydride, succinic anhydride, itaconic anhydride, O-phthalic in one of the embodiments,
Acid anhydrides, tetrabydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, Jia Qiao-be interior-tetrahydro neighbour's benzene
Dicarboxylic acid anhydride, methyl first bridge-interior-tetrabydrophthalic anhydride, methyl tetrahydrophthalic anhydride etc., trimellitic anhydride, equal benzene
One of tetracarboxylic acid anhydride and benzophenone tetrabasic carboxylic acid dicarboxylic anhydride are a variety of.
The present invention also provides a kind of alkali solubility UV-cured resin containing urethano.
A kind of alkali solubility UV-cured resin containing urethano, by the alkali solubility ultraviolet light of the present invention containing urethano
The preparation method of solidified resin is prepared.
Urethano is introduced in the above-mentioned strand that the alkali solubility UV-cured resin containing urethano is prepared, in turn
Enhance the flexibility and adhesiveness of UV-cured resin.In addition, being introduced in above-mentioned resin structure multiple acrylate-based
Group, painting film strength is further increased after increasing crosslink density solidification.
The present invention also provides the ultraviolet light curing anti-etching materials for including the alkali solubility UV-cured resin containing urethano
Material.
A kind of ultraviolet light solidification etch-resistant material of the alkali solubility UV-cured resin containing urethano.The UV light
The raw material for changing etch-resistant material includes each component of following mass percentage:
The above-mentioned alkali solubility UV-cured resin containing urethano contains urethano and carboxyl simultaneously, the purple comprising this resin
There is excellent adhesive force with the copper face of substrate after outer photocureable etching-resistant material solidification.In addition, being introduced in above-mentioned resin structure
Multiple acrylate groups, increase crosslink density, the intensity of resin is further increased after film-forming.Therefore,
Ultraviolet light solidification etch-resistant material in etching process comprising the resin is not easy to be etched, and then PCB can be effectively protected
The substrate of plate is not corroded.
Furthermore in taking off membrane process, ultraviolet light solidification etch-resistant material meeting full wafer shape is attached at copper face, and then is conducive to winder
Machine to ultraviolet light solidification etch-resistant material quickly collected, raising recovery efficiency, reduce the processing difficulty for taking off film liquid and at
This.It will not be broken into a large amount of fractionlet shapes as traditional ultraviolet light solidifies etch-resistant material and be dissolved in or be dispersed in and take off film liquid
In, it is difficult to it collects.
The photoinitiator is 2- hydroxy-2-methyl-1- phenylacetone-1,2- methyl-1-in one of the embodiments,
(4- first mercaptophenyl) -2- morpholine acetone -1,2- phenyl -2- dimethylamino -1- (4- morpholinyl phenyl)-butanone -1,2- ethyl anthracene
Quinone, isopropyl thioxanthone, 2,4- diethyl thioxanthone, 2,4,6- trimethylbenzoyl diphenyl phosphine oxide, bis- (2,4,6-
Trimethylbenzoyl) phenyl phosphine oxide, bis- (2,6- bis- fluoro- 3- (1H- pyrrole radicals -1) phenyl) luxuriant titanium, 9- anthracene methyl N, N- bis-
One of ethyl carbamate, 2- (3- benzoylphenyl) propionic acid guanidine and 1- (anthraquinone -2- base) ethyl imidazol(e) carboxylate
Or it is a variety of.
In one of the embodiments, the acrylic ester monomer be n-butyl acrylate, senecioate-hydroxyl ethyl ester,
2- phenoxyethyl acrylate, iso-bornyl acrylate, 1,6-HD double methacrylate, the double acrylic acid of two contracting propylene glycol
Ester, tripropylene glycol double methacrylate, Ethoxylated bisphenol A dimethylacrylate, two propylene of diethoxy neopentyl glycol
Acid esters, ethoxylated neopentylglycol diacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, three
One of three propylene acid esters of (2- ethoxy) isocyanates and double pentaerythritol methacrylate are a variety of.
Specific embodiment
In order to make the objectives, technical solutions, and advantages of the present invention clearer, right below in conjunction with specific embodiment
The present invention is further elaborated.It should be appreciated that the specific embodiments described herein are only used to explain the present invention,
It is not intended to limit the present invention.
Unless otherwise defined, all technical and scientific terms used herein and belong to technical field of the invention
The normally understood meaning of technical staff is identical.Term as used herein in the specification of the present invention is intended merely to description tool
The purpose of the embodiment of body, it is not intended that in the limitation present invention.Term " and or " used herein includes one or more
Any and all combinations of relevant listed item.
The preparation method of the present invention provides a kind of alkali solubility UV-cured resin containing urethano, the preparation method
The following steps are included:
Diisocyanate and dibutyl tin dilaurate are added separately in the not acrylate monomer of hydroxyl, then
Pentaerythritol triacrylate is added and obtains the first reaction system, is kept for 40 DEG C -70 DEG C of reaction temperature, monitors the first reaction system
In diisocyanate-changes of contents of NCO group, when the content of described-NCO group is the 48%-55% of initial content
Stop reaction, obtains half addition product of diisocyanate.
Half addition product of diisocyanate is added in polyalcohol and obtains the second reaction system, holding reaction temperature is
40 DEG C -80 DEG C, when in half addition product of the second reaction system diisocyanate-content of NCO group be 0 when stop reaction to get
To the alkali solubility UV-cured resin precursor containing urethano.
Wherein, urethano, terminal hydroxy group are contained in the alkali solubility UV-cured resin precursor containing urethano.
Organic acid anhydride is added in the alkali solubility UV-cured resin precursor containing urethano and obtains third reaction
System, keeping reaction temperature is 60 DEG C -90 DEG C, is stopped when the acid value in third reaction system is 60mgKOH/g-120mgKOH/g
It only reacts to get the alkali solubility UV-cured resin containing urethano is arrived.
In one embodiment, the diisocyanate be methyl diphenylene diisocyanate, it is toluene di-isocyanate(TDI), different
One of isophorone diisocyanate and hexamethylene diisocyanate are a variety of.
In one embodiment, the acrylate monomer of the not hydroxyl is isobornyl acrylate, methacrylic acid
Isobornyl thiocyanoacetate, ethoxyethoxyethyl acrylate, 2- phenoxyethyl acrylate, diethylene glycol dimethacrylate
Ester, tripropylene glycol diacrylate, dipropylene glycol diacrylate, neopentylglycol diacrylate, two propylene of 1,6-HD
Acid esters, trimethylolpropane trimethacrylate, trimethylol-propane trimethacrylate and ethyoxyl trimethylolpropane tris
One of acrylate is a variety of.
In one embodiment, the polyalcohol is polyethylene glycol, ethylene glycol, 1,2-PD, 1,4-butanediol, 1,6-
One of hexylene glycol, neopentyl glycol, dipropylene glycol, polyether Glycols, polyester diol, trimethylolpropane and glycerol
Or it is a variety of.
In one embodiment, the organic acid anhydride be maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride,
Tetrabydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, Jia Qiao-be interior-tetrahydrophthalic acid
Acid anhydride, methyl first bridge-interior-tetrabydrophthalic anhydride, methyl tetrahydrophthalic anhydride etc., trimellitic anhydride, Pyromellitic Acid
One of acid anhydride and benzophenone tetrabasic carboxylic acid dicarboxylic anhydride are a variety of.
In one embodiment, the molar ratio of the pentaerythritol triacrylate and the diisocyanate is 1:(1-
1.05)；The mass ratio of the diisocyanate and the dibutyl tin dilaurate is 100:(0.1-1)；The diisocyanate
The mass ratio of the acrylate monomer of ester and the not hydroxyl is 1:(0.1-0.3)；Half addition product of diisocyanate with
The molar ratio of polyalcohol is 1:(1-1.05)；Anhydride group and the alkali solubility containing urethano in the organic acid anhydride is ultraviolet
The molar ratio of the hydroxyl of photocurable resin precursor is (0.5-1): 1.
In one embodiment, in the first, second reaction system-monitoring of the content of NCO group passes through di-n-butylamine
Titrimetric standard measurement.
The preparation process of the above-mentioned alkali solubility UV-cured resin containing urethano is simple, and the alkali containing urethano is prepared
Urethano is introduced in the strand of dissolubility UV-cured resin, and then is enhanced the flexibility of UV-cured resin and glued
Attached property.In addition, introducing multiple acrylate groups in above-mentioned resin structure, crosslink density is increased, film is strong after solidification
Degree is further increased.Furthermore the above-mentioned alkali solubility UV-cured resin containing urethano contains carboxyl, there is alkali soluble
Property.
The present invention also provides a kind of alkali solubility UV-cured resin containing urethano.
A kind of alkali solubility UV-cured resin containing urethano, it is ultraviolet by the alkali solubility of the present invention containing urethano
The preparation method of light-cured resin is prepared.
Urethano is introduced in the above-mentioned strand that the alkali solubility UV-cured resin containing urethano is prepared, in turn
Enhance the flexibility and adhesiveness of UV-cured resin.In addition, being introduced in above-mentioned resin structure multiple acrylate-based
Group, painting film strength is further increased after increasing crosslink density solidification.
The present invention also provides it is a kind of include the alkali solubility UV-cured resin containing urethano ultraviolet light curing anti-etching
Material.
A kind of includes the ultraviolet light solidification etch-resistant material of the alkali solubility UV-cured resin containing urethano, described ultraviolet
The raw material of photocureable etching-resistant material includes each component of following mass percentage:
In one embodiment, the photoinitiator is 2- hydroxy-2-methyl-1- phenylacetone-1,2- methyl-1-(4-
First mercaptophenyl) -2- morpholine acetone -1,2- phenyl -2- dimethylamino -1- (4- morpholinyl phenyl)-butanone -1,2- ethyl hydrazine,
Isopropyl thioxanthone, 2,4- diethyl thioxanthone, 2,4,6- trimethylbenzoyl diphenyl phosphine oxide, bis- (2,4,6- tri-
Methyl benzoyl) phenyl phosphine oxide, bis- (2,6- bis- fluoro- 3- (1H- pyrrole radicals -1) phenyl) luxuriant titanium, 9- anthracene methyl N, N- diethyl
One of aminocarbamic acid ester, 2- (3- benzoylphenyl) propionic acid guanidine and 1- (anthraquinone -2- base) ethyl imidazol(e) carboxylate or
It is a variety of.
In one embodiment, acrylic ester monomer is n-butyl acrylate, senecioate-hydroxyl ethyl ester, 2- benzene oxygen second
Base acrylate, iso-bornyl acrylate, 1,6-HD double methacrylate, two contracting propylene glycol double methacrylates, three contractings third
Diol acrylate, Ethoxylated bisphenol A dimethylacrylate, diethoxy neopentylglycol diacrylate, the third oxygen
Base neopentylglycol diacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, three (2- ethoxys)
One of three propylene acid esters of isocyanates and double pentaerythritol methacrylate are a variety of.
In one embodiment, the pigment is in phthalocyanine green, phthalocyanine blue, azophosphine, azophloxine, carbon black and titanium dioxide
It is one or more.Wherein, preferred phthalocyanine blue.
The filler is talcum powder, barium sulfate, silicon powder, kaolin, mica powder and carbonic acid in one of the embodiments,
One of calcium is a variety of.
The thixotropic agent is fumed silica HL-200, organobentonite, hydrogenated castor in one of the embodiments,
One of oil, polyethylene wax are a variety of.
The above-mentioned alkali solubility UV-cured resin containing urethano contains urethano and carboxyl simultaneously, the purple comprising this resin
There is excellent adhesive force with the copper face of substrate after outer photocureable etching-resistant material solidification.In addition, being introduced in above-mentioned resin structure
Multiple acrylate groups, increase crosslink density, coating strength is further increased after film-forming.Therefore, In
Ultraviolet light solidification etch-resistant material in etching process comprising the resin is not easy to be etched, and then pcb board can be effectively protected
Substrate be not corroded.
Furthermore in taking off membrane process, ultraviolet light solidification etch-resistant material meeting full wafer shape is attached at copper face, and then is conducive to winder
Machine to ultraviolet light solidification etch-resistant material quickly collected, raising recovery efficiency, reduce the processing difficulty for taking off film liquid and at
This.It will not be broken into a large amount of fractionlet shapes as traditional ultraviolet light solidifies etch-resistant material and be dissolved in or be dispersed in and take off film liquid
In, it is difficult to it collects.
The following are specific embodiment parts.
Embodiment 1
A kind of preparation method of the alkali solubility UV-cured resin containing urethano:
222.24g isophorone diisocyanate, 1.10g dibutyl tin dilaurate are added separately to 44.00g diethyl
In diol dimethacrylate, 298.29g pentaerythritol triacrylate is added dropwise, is kept for 40 DEG C -70 DEG C of reaction temperature, when the
In one reaction system-content of NCO group when being the 50% of initial content cooling stop reaction, obtain half addition of diisocyanate
Object.
Above-mentioned half addition product of diisocyanate is added in 62.07g ethylene glycol again, is kept for 40 DEG C -80 DEG C of reaction temperature,
When monitor in the second reaction system-content of NCO group be 0 when, be down to room temperature and stop reaction to get to the alkali containing urethano
Dissolubility UV-cured resin precursor.
Then 152.15g tetrahydrophthalic anhydride is added in the alkali solubility UV-cured resin precursor containing urethano, keeps temperature
Degree is at 60 DEG C -90 DEG C, when monitoring that acid value in third reaction system is 72mgKOH/g, is down to room temperature and stops reaction to get arriving
Alkali solubility UV-cured resin containing urethano, is denoted as A1.
Embodiment 2
A kind of preparation method of the alkali solubility UV-cured resin containing urethano:
222.24g isophorone diisocyanate, 1.10g dibutyl tin dilaurate are added separately to 44.00g diethyl
In diol dimethacrylate, 298.29g pentaerythritol triacrylate is added dropwise, is kept for 40 DEG C -70 DEG C of reaction temperature, when the
In one reaction system-content of NCO group when being the 50% of initial content cooling stop reaction, obtain half addition of diisocyanate
Object；
Half addition product of diisocyanate is added in 200.00g polyethylene glycol, maintains the temperature at 40 DEG C -80 DEG C,
When monitor in the second reaction system-content of NCO group be 0 when, be down to room temperature and stop reaction to get to the alkali containing urethano
Dissolubility UV-cured resin precursor.
Then 152.15g tetrahydrophthalic anhydride is added in the alkali solubility UV-cured resin precursor containing urethano, is protected
Temperature is held at 60 DEG C -90 DEG C, when monitoring that acid value in third reaction system is 61mgKOH/g, room temperature is down to and stops reaction, i.e.,
The alkali solubility UV-cured resin containing urethano is obtained, A2 is denoted as.
Embodiment 3
A kind of preparation method of the alkali solubility UV-cured resin containing urethano:
222.24g isophorone diisocyanate, 1.10g dibutyl tin dilaurate are added separately to 44.00g diethyl
In diol dimethacrylate, 298.29g pentaerythritol triacrylate is added dropwise, is kept for 40 DEG C -70 DEG C of reaction temperature, when the
In one reaction system-content of NCO group when being the 50% of initial content cooling stop reaction, obtain half addition of diisocyanate
Object；
Half addition product of diisocyanate is added in 134.17g trimethylolpropane, maintains the temperature at 40 DEG C -80
DEG C, when monitor in the second reaction system-content of NCO group be 0 when, be reduced to room temperature to stop reaction to get to containing urethane
The alkali solubility UV-cured resin precursor of base.
Then 152.15g tetrahydrophthalic anhydride is added in the alkali solubility UV-cured resin precursor containing urethano, is protected
Temperature is held at 60 DEG C -90 DEG C, monitors that the acid value in third reaction system is 112mgKOH/g, is down to room temperature and stops reaction, i.e.,
The alkali solubility UV-cured resin containing urethano is obtained, A3 is denoted as.
Embodiment 4
A kind of ultraviolet light of the alkali solubility UV-cured resin containing urethano solidifies the preparation of etch-resistant material:
Each component is configured to the alkali solubility UV-cured resin containing urethano by the mass percentage that table 1 is listed
Ultraviolet light solidifies etch-resistant material.The each component that table 1 is listed is uniformly mixed, is ground to fineness less than 25 μ with three-roll grinder
M sticks to 150dPas with hydroxyethyl methacrylate tune, obtains the purple of the alkali solubility UV-cured resin containing urethano
Outer photocureable etching-resistant material.The ultraviolet light solidification etch-resistant material of the alkali solubility UV-cured resin containing urethano is led to
120T silk-screen printing is crossed on copper-clad plate surface, is solidified with UV machine, solidification energy 1500mJ/cm2, then lost through acidity
It carves, sodium hydroxide solution takes off film, film gatherer winder to get the figuratum wiring board of etching is arrived.
Table 1
Infuse 1:KAYARADER-4010W, acid value 150mgKOH/g-175mgKOH/g, chemical drug chemical industry (Wuxi) Co., Ltd.
Infuse 2:2- ethyl hydrazine, Hengqiao Stock Co., Ltd..
Note 3: phthalocyanine blue 5380E, Japanese DIC.
Note 4: talcum powder, 3000 mesh, Guangxi Long Guang talcum development corporation, Ltd..
Note 5: hydroxyethyl methacrylate, Jiangsu Miki Chemical Co., Ltd
Note 6: fumed silica HL-200, Guangzhou Science and Technology Ji Sheng Industrial Co.
The performance test that ultraviolet light including the alkali solubility UV-cured resin containing urethano solidifies etch-resistant material is commented
Price card is quasi- as follows:
(1) adhesive force
Referring to GB/T9286-1998 " the drawing lattice experiment of paint and varnish paint film ".Coating is only crossed entirely without falling off to be excellent
Edge have on a small quantity fall off be it is good, there is extra 5% to fall off for difference.
(2) pencil hardness
Referring to hardness of film after GB/T6739-2006 " paint and varnish pencil method measures hardness of paint film " test solidification.
(3) etch-resistance
It etches section and uses acidic etching liquid CC-330 (pine and cypress industry development Co., Ltd, Shenzhen), 48-55 DEG C of temperature, when
Between 60s, pressure 3.0kgf/cm2.After overetch section, referring to GB/T9286-1998 " the drawing lattice experiment of paint and varnish paint film ".
Coating entirely without falling off to be excellent, only scribing edge have on a small quantity fall off be it is good, there is extra 5% to fall off for difference.
(4) the film time is taken off
Taking off film section and taking off film liquid is 5%NaOH aqueous solution, and temperature is by 45 ± 2 DEG C.Film can be from copper-clad plate after crossing film gatherer
The complete striping clean shortest time.
(5) state that ultraviolet light after film solidifies etch-resistant material is taken off
After taking off film, before crossing and taking off film machine, ultraviolet light solidification etch-resistant material is mainly that continuous sheet attaches and copper face, or with
Fractionlet shape disperses and takes off in film liquid.
(6) winder efficiency
The film that film gatherer is collected into weighs quality, is denoted as m in 100 DEG C of baking 5h1.The ink quality note of printing consumption
For m0。
Winder efficiency=m1/m0× 100%
Table 2
Known by table 2, etch-resistant material 1,2 and 3 is solidified by the ultraviolet light of the alkali solubility UV-cured resin containing urethano
Adhesive force, etch-resistance are qualified after solidification, pencil hardness 1H, ultraviolet with being prepared by resin containing KAYARADER-4010W
Ultraviolet light solidification etch-resistant material (control group) of light-cured resin is consistent.
It is also known from table 2, the ultraviolet light solidification etch-resistant material 1 of the alkali solubility UV-cured resin containing urethano,
2,3 take off ultraviolet light solidification etch-resistant material ultraviolet light solidification etch-resistant material after film and are mainly attached at copper face with full wafer shape, compare
Group, which is mainly scattered in fractionlet shape, to take off in film liquid, so the alkali solubility UV-cured resin containing urethano in the present invention
The winder efficiency that ultraviolet light solidifies etch-resistant material is much higher than control group.
Each technical characteristic of the above embodiment can be combined arbitrarily, for simplicity of description, not to above-mentioned implementation
The all possible combination of each technical characteristic in example is all described, as long as however, the combination of these technical characteristics is not present
Contradiction all should be considered as described in this specification.
Only several embodiments of the present invention are expressed for the above embodiment, and the description thereof is more specific and detailed, but not
It can therefore be construed as limiting the scope of the patent.It should be pointed out that for those of ordinary skill in the art,
Without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to protection model of the invention
It encloses.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (10)
1. a kind of preparation method of the alkali solubility UV-cured resin containing urethano, which is characterized in that the preparation method packet
Include following steps:
Diisocyanate and dibutyl tin dilaurate are added separately in the not acrylate monomer of hydroxyl, are then added
Pentaerythritol triacrylate obtains the first reaction system, is kept for 40 DEG C -70 DEG C of reaction temperature, monitors two in the first reaction system
Isocyanates-changes of contents of NCO group, stop when the content of described-NCO group is the 48%-55% of initial content
Reaction, obtains half addition product of diisocyanate；
Half addition product of diisocyanate is added in polyalcohol and obtains the second reaction system, keeping reaction temperature is 40
DEG C -80 DEG C, when in the second reaction system-content of NCO group be 0 when stop reaction to get purple to the alkali solubility containing urethano
Outer photocurable resin precursor；
Organic acid anhydride is added in the alkali solubility UV-cured resin precursor containing urethano and obtains third reaction system,
Keeping reaction temperature is 60 DEG C -90 DEG C, is stopped when the acid value in third reaction system is 60mgKOH/g-120mgKOH/g anti-
Should to get arrive the alkali solubility UV-cured resin containing urethano.
2. the preparation method of the alkali solubility UV-cured resin according to claim 1 containing urethano, which is characterized in that
The molar ratio of the pentaerythritol triacrylate and the diisocyanate is 1:(1-1.05)；The diisocyanate and institute
The mass ratio for stating dibutyl tin dilaurate is 100:(0.1-1)；The acrylic acid of the diisocyanate and the not hydroxyl
The mass ratio of ester monomer is 1:(0.1-0.3)；The molar ratio of half addition product of diisocyanate and polyalcohol is 1:(1-
1.05)；The hydroxyl in anhydride group and the alkali solubility UV-cured resin precursor containing urethano in the organic acid anhydride
The molar ratio of base is (0.5-1): 1.
3. the preparation method of the alkali solubility UV-cured resin according to claim 1 or 2 containing urethano, feature exist
In the diisocyanate is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), isophorone diisocyanate and six
One of methylene diisocyanate is a variety of.
4. the preparation method of the alkali solubility UV-cured resin according to claim 1 or 2 containing urethano, described to be free of
The acrylate monomer of hydroxyl is isobornyl acrylate, isobornyl methacrylate, ethoxyethoxyethyl acrylic acid
Ester, 2- phenoxyethyl acrylate, dimethacrylate, tripropylene glycol diacrylate, dipropylene glycol two
Acrylate, neopentylglycol diacrylate, 1,6 hexanediol diacrylate, trimethylolpropane trimethacrylate, three hydroxyls
One of trimethacrylate and ethyoxyl trimethylolpropane trimethacrylate are a variety of.
5. the preparation method of the alkali solubility UV-cured resin according to claim 1 or 2 containing urethano, feature exist
In, the polyalcohol be ethylene glycol, 1,2-PD, 1,4-butanediol, 1,6- hexylene glycol, neopentyl glycol, dipropylene glycol,
One of polyether Glycols, polyester diol, trimethylolpropane and glycerol are a variety of.
6. the preparation method of the alkali solubility UV-cured resin according to claim 1 or 2 containing urethano, feature exist
In the organic acid anhydride is maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrabydrophthalic anhydride, six
Hydrogen phthalic anhydride, methylhexahydrophthalic anhydride, Jia Qiao-be interior-tetrabydrophthalic anhydride, methyl first bridge-interior-tetrahydro
Phthalic anhydride, methyl tetrahydrophthalic anhydride, trimellitic anhydride, pyromellitic dianhydride and benzophenone tetracarboxylic acid acid diacid
One of acid anhydride is a variety of.
7. a kind of alkali solubility UV-cured resin containing urethano, which is characterized in that contain as described in claim any one of 1-6
The preparation method of the alkali solubility UV-cured resin of urethano is prepared.
8. a kind of includes the ultraviolet light solidification etch-resistant material of the alkali solubility UV-cured resin containing urethano, feature exists
In each component that the raw material that, the ultraviolet light solidifies etch-resistant material includes following mass percentage:
The feed components content that the ultraviolet light solidifies etch-resistant material is 100%.
9. the ultraviolet light curing anti-etching material of the alkali solubility UV-cured resin according to claim 8 containing urethano
Material, which is characterized in that the photoinitiator is 2- hydroxy-2-methyl-1- phenylacetone-1,2- methyl-1-(4- first sulfydryl benzene
Base) -2- morpholine acetone -1,2- phenyl -2- dimethylamino -1- (4- morpholinyl phenyl)-butanone -1,2- ethyl hydrazine, isopropyl sulphur
Miscellaneous anthrone, 2,4- diethyl thioxanthone, 2,4,6- trimethylbenzoyl diphenyl phosphine oxide, bis- (2,4,6- trimethylbenzene first
Acyl group) phenyl phosphine oxide, bis- (2,6- bis- fluoro- 3- (1H- pyrrole radicals -1) phenyl) luxuriant titanium, 9- anthracene methyl N, N- diethylacbamazine
One of acid esters, 2- (3- benzoylphenyl) propionic acid guanidine and 1- (anthraquinone -2- base) ethyl imidazol(e) carboxylate are a variety of.
10. the ultraviolet light curing anti-etching of the alkali solubility UV-cured resin containing urethano according to claim 8 or claim 9
Material, which is characterized in that the acrylic ester monomer is n-butyl acrylate, senecioate-hydroxyl ethyl ester, 2- benzene oxygen ethyl third
Olefin(e) acid ester, iso-bornyl acrylate, 1,6-HD double methacrylate, two contracting propylene glycol double methacrylates, tripropylene glycol
Double methacrylate, Ethoxylated bisphenol A dimethylacrylate, diethoxy neopentylglycol diacrylate, propoxylation
Neopentylglycol diacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, three (2- ethoxy) isocyanides
One of three propylene acid esters of acid esters and double pentaerythritol methacrylate are a variety of.
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| CN101935494A (en) * | 2010-08-18 | 2011-01-05 | 梁鹏飞 | Ultraviolet-cured resin composition and preparation method thereof |
| CN103275551A (en) * | 2013-05-14 | 2013-09-04 | 西安理工大学 | Flexography waterborne ultraviolet (UV) printing ink and preparation method thereof |
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