JPS63205649A - Liquid photo solder resist composition - Google Patents
Liquid photo solder resist compositionInfo
- Publication number
- JPS63205649A JPS63205649A JP3784787A JP3784787A JPS63205649A JP S63205649 A JPS63205649 A JP S63205649A JP 3784787 A JP3784787 A JP 3784787A JP 3784787 A JP3784787 A JP 3784787A JP S63205649 A JPS63205649 A JP S63205649A
- Authority
- JP
- Japan
- Prior art keywords
- parts
- epoxy
- compd
- maleic anhydride
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 239000007788 liquid Substances 0.000 title claims description 25
- 229910000679 solder Inorganic materials 0.000 title abstract description 20
- 239000004593 Epoxy Substances 0.000 claims abstract description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 20
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229920003986 novolac Polymers 0.000 claims abstract description 12
- 239000003822 epoxy resin Substances 0.000 claims abstract description 11
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 6
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 claims abstract description 5
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims abstract 3
- 229930003836 cresol Natural products 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 5
- FSYPIGPPWAJCJG-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1CO1 FSYPIGPPWAJCJG-UHFFFAOYSA-N 0.000 claims description 4
- ZAUYNCUCMJDAHW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;hydrogen peroxide;molecular iodine Chemical compound OO.II.C=CN1CCCC1=O ZAUYNCUCMJDAHW-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 230000010287 polarization Effects 0.000 claims 1
- 238000010526 radical polymerization reaction Methods 0.000 claims 1
- 238000007747 plating Methods 0.000 abstract description 10
- 150000002148 esters Chemical class 0.000 abstract description 4
- 238000013329 compounding Methods 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 21
- -1 2-hydroxypropyl Chemical group 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 7
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000003860 storage Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000007664 blowing Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RJDOZRNNYVAULJ-UHFFFAOYSA-L [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[Si+4].[Si+4].[Si+4].[K+] Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[Si+4].[Si+4].[Si+4].[K+] RJDOZRNNYVAULJ-UHFFFAOYSA-L 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- JMLIYQBCNLVLNQ-UHFFFAOYSA-N 3-methylbutyl 2,3-dimethylbenzoate Chemical compound CC(C)CCOC(=O)C1=CC=CC(C)=C1C JMLIYQBCNLVLNQ-UHFFFAOYSA-N 0.000 description 2
- ORDRGXFSRBRQQG-UHFFFAOYSA-N 6-methylheptyl 2-sulfanylpropanoate Chemical compound CC(C)CCCCCOC(=O)C(C)S ORDRGXFSRBRQQG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing Of Printed Circuit Boards (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の目的〕
(産業上の利用分野)
本発明は、印刷回路製造工程などにおいて好適に用いら
れ、紫外線などの放射線による露光および弱アルカリ水
溶液による現像の後に、すぐれたハンダメッキ耐性を発
現する液状フォトソルダーレジスト組成物に関する。Detailed Description of the Invention [Objective of the Invention] (Industrial Application Field) The present invention is suitably used in printed circuit manufacturing processes, etc., and provides excellent The present invention relates to a liquid photosolder resist composition that exhibits solder plating resistance.
(従来の技術)
従来、液状フォトソルダーレジストとしては、n□光1
.1,1.1−トリクロロエタンなどのハロゲン系有機
溶剤により現像される溶剤現像型のものが知られていた
。しかしながら、ハロゲン系有機溶剤は有機溶剤の中で
は毒性が高く1作業環境保全、大気汚染防止などの面か
ら9弱アルカリ水溶液により現像されるアルカリ現像型
のものへの転換が望まれていた。(Prior art) Conventionally, as a liquid photo solder resist, n□light 1
.. A solvent-developable type that is developed using a halogenated organic solvent such as 1,1,1-trichloroethane has been known. However, halogen-based organic solvents are highly toxic among organic solvents, and from the viewpoint of protecting the working environment and preventing air pollution, it has been desired to switch to an alkaline developing type in which development is performed using a 9 weak alkali aqueous solution.
しかしながら、これまで提案さたアルカリ現像型の液状
フォトソルダーレジスト組成物は、冷暗所においても硬
化が徐々に進行し、数日から1iPi間程度でゲル化す
るため、使用直前に硬化剤を混合する二液型として用い
られており、二液を計量混合する面倒がある上に、印刷
塗工後に残った液状フォトソルダーレジスト組成物の再
使用が困難であるという欠点があった。However, the alkali-developable liquid photo solder resist compositions that have been proposed so far harden gradually even in a cool and dark place and gel in a few days to about 1 iPi, so it is necessary to mix a curing agent immediately before use. It is used as a liquid type, and has the disadvantage that it is troublesome to measure and mix the two components and that it is difficult to reuse the liquid photo solder resist composition remaining after printing and coating.
(発明が解決しようとする問題点)
本発明は、上記の種々の欠点を改良し、貯蔵安定性にす
ぐれ一液型としても使用可能で1弱アルカリ水溶液で現
像することができ、露光現象後にすぐれたハンダメッキ
耐性を発現する液状フォトソルダーレジスト組成物を提
供するものである。(Problems to be Solved by the Invention) The present invention improves the various drawbacks mentioned above, has excellent storage stability, can be used as a one-component type, can be developed with a slightly weak alkaline aqueous solution, and has a The present invention provides a liquid photosolder resist composition that exhibits excellent solder plating resistance.
(問題点を解決するための手段)
本発明は、無水マレイン酸および(または)無水イタコ
ン酸10モル%以上と無水マレイン酸および無水イタコ
ン酸以外のラジカル重合性モノマー90モル%以下とを
共重合して得られる共重合の無水マレイン酸および無水
イタコン酸成分1モルに対して。(Means for Solving the Problems) The present invention is a method of copolymerizing 10 mol% or more of maleic anhydride and/or itaconic anhydride with 90 mol% or less of a radically polymerizable monomer other than maleic anhydride and itaconic anhydride. per mole of maleic anhydride and itaconic anhydride components of the copolymerized product obtained by
ラジカル重合性の一価アルコールおよび(または)一価
エポキシ化合物、および必要に応じてラジカル重合性で
ない一価アルコールおよび(または)一価エポキシ化合
物0.05〜0.95モルの割合で反応させて得られる
エステル化物(A)、およびトリグリシジルイソシアヌ
レート、ハイドロキノンジグリシジルエーテル、ビスフ
ェノールSジグリシジルエーテル、タレゾールノボラッ
ク型エポキシ樹脂およびフェノールノボラック型エポキ
シ樹脂から選ばれる1種または2種以上のエポキシ化合
物(B)からなる混合物100重量部、前記(A)以外
のエポキシ基を有さないラジカル重合性化合物(C)1
0〜200重量部、および必要に応じて有機溶剤(D)
からなる液状フォトソルダーレジスト組成物である。A radically polymerizable monohydric alcohol and (or) a monohydric epoxy compound, and optionally a non-radically polymerizable monohydric alcohol and (or) a monohydric epoxy compound are reacted at a ratio of 0.05 to 0.95 mol. The resulting esterified product (A), and one or more epoxy compounds selected from triglycidyl isocyanurate, hydroquinone diglycidyl ether, bisphenol S diglycidyl ether, Talezol novolac type epoxy resin, and phenol novolac type epoxy resin ( 100 parts by weight of a mixture consisting of B), 1 radically polymerizable compound (C) having no epoxy group other than the above (A)
0 to 200 parts by weight, and an organic solvent (D) if necessary
A liquid photosolder resist composition consisting of:
本発明において無水マレイン酸および(または)無水イ
タコン酸と共重合される無水マレイン酸および無水イタ
コン酸以外のラジカル重合性モノマーとしては、無水マ
レイン酸および(または)無水イタコン酸とゲル化せず
に共重合可能なモノマーであり。In the present invention, the radically polymerizable monomers other than maleic anhydride and itaconic anhydride to be copolymerized with maleic anhydride and/or itaconic anhydride include those that do not gel with maleic anhydride and/or itaconic anhydride. It is a copolymerizable monomer.
無水酸基と反応するエポキシ基、イソシアネート基。Epoxy groups and isocyanate groups that react with acid anhydride groups.
水酸基、あるいはアミノ基などの活性基を有しないモノ
マーである。このようなモノマーとしては、スチレン、
α−メチルスチレンなどのスチレン系モノマー類、メチ
ル(メタ)アクリレートエチル(メタ)アクリレート、
ブチル(メタ)アクリレートなどの(メタ)アクリル酸
アルキルエステル類、酢酸ビニルなどあるいはこれらの
混合物を用いることができるが、得られる液状フォトソ
ルダーレジスト組成物の露光現像後の硬度の面からは、
スチレン、α−メチルスチレン、メチルメタアクリレー
ト、あるいはこれらの混合物を主成分とするものを用い
ることが好ましい。また2本発明の液状フォトソルダー
レジスト組成物の性能を阻害しない範囲で、 (メタ)
アクリル酸、マレイン酸などの不飽和酸を含んでいても
よい。It is a monomer that does not have active groups such as hydroxyl groups or amino groups. Such monomers include styrene,
Styrenic monomers such as α-methylstyrene, methyl (meth)acrylate, ethyl (meth)acrylate,
(Meth)acrylic acid alkyl esters such as butyl (meth)acrylate, vinyl acetate, etc., or mixtures thereof can be used, but in terms of the hardness of the obtained liquid photosolder resist composition after exposure and development,
It is preferable to use a material containing styrene, α-methylstyrene, methyl methacrylate, or a mixture thereof as a main component. 2. (Meta) within the range that does not impede the performance of the liquid photosolder resist composition of the present invention.
It may also contain unsaturated acids such as acrylic acid and maleic acid.
無水マレイン酸および(または)無水イタコン酸10モ
ル%以上と無水マレイン酸および無水イタコン酸以外の
モノマー90モル%以下とが共重合され共重合物とされ
る。無水マレイン酸および(または)無水イタコン酸の
量が10モル%未満の場合には、露光後、未露光部分の
弱アルカリ水溶液への溶解性が低くなるとともに、露光
部分のハンダメッキ耐性が低くなる。A copolymer is obtained by copolymerizing 10 mol% or more of maleic anhydride and/or itaconic anhydride with 90 mol% or less of a monomer other than maleic anhydride and itaconic anhydride. If the amount of maleic anhydride and/or itaconic anhydride is less than 10 mol%, after exposure, the solubility of the unexposed part in a weak alkaline aqueous solution becomes low, and the solder plating resistance of the exposed part becomes low. .
得られた共重合物の無水マレイン酸および無水イタコン
酸成分1モルに対して、ラジカル重合性の一価アルコー
ルおよび(または)一価エポキシ化合物。radically polymerizable monohydric alcohol and/or monohydric epoxy compound per mol of maleic anhydride and itaconic anhydride components of the obtained copolymer.
および必要に応じてラジカル重合性でない一価アルコー
ルおよび(または)一価エポキシ化合物0.05〜0.
95モルの割合で反応させて、エステル化物(A)が得
られる。and, if necessary, a monohydric alcohol and/or monohydric epoxy compound that is not radically polymerizable.
The esterified product (A) is obtained by reacting at a ratio of 95 moles.
ラジカル重合性の一価アルコールとしては、2−ヒドロ
キシエチル(メタ)アクリレート、2−ヒドロキシプロ
ピル(メタ)アクリレート、3−ヒドロキシブチル(メ
タ)アクリレートなどの水酸基含有(メタ)アクリル酸
エステル、アリルアルコールなど、あるいはこれらの混
合物を用いることができるが、得られる共重合物の無水
マレイン酸および無水イタコン酸成分とのエステル化反
応が速く、エステル化物(A)の露光時の硬化反応が速
いことから。Examples of radically polymerizable monohydric alcohols include hydroxyl group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 3-hydroxybutyl (meth)acrylate, allyl alcohol, etc. , or a mixture thereof can be used, since the esterification reaction with the maleic anhydride and itaconic anhydride components of the resulting copolymer is fast, and the curing reaction of the esterified product (A) upon exposure is fast.
2−ヒドロキシエチル(メタ)アクリレートを用いるこ
とが好ましい、また、ラジカル重合性の一価エボキシ化
合物としては、グリシジル(メタ)アクリレート、アリ
ルグリシジルエーテル、シクロヘキセンビニルモノエポ
キサイドなど、あるいはこれらの混合物を用いることが
できる。It is preferable to use 2-hydroxyethyl (meth)acrylate, and as the radically polymerizable monovalent epoxy compound, glycidyl (meth)acrylate, allyl glycidyl ether, cyclohexene vinyl monoepoxide, etc., or a mixture thereof may be used. Can be done.
また、得られるエステル化物(A)のエチレン性二重結
合の密度すなわち露光時の硬化性と弱アルカリ水溶液へ
の溶解性とのバランスを調節するために。Further, in order to adjust the density of ethylenic double bonds of the obtained esterified product (A), that is, the balance between curability upon exposure and solubility in a weak alkaline aqueous solution.
上記のラジカル重合性の一価アルコールおよび(または
)一価エポキシ化合物に、ラジカル重合性でない一価ア
ルコールおよび(または)一価エポキシ化合物を併用す
ることもできる。このようなラジカル重合性でない一価
アルコールには、メタノール、エタノール、プロピルア
ルコール、ブタノールなどの脂肪族一価アルコール、ベ
ンジルアルコール、フェノールやアルキルフェノールの
アルキレンオキサイド付加物などの芳香族アルコール、
シクロヘキサノールなどの脂環族アルコールなど、ある
いはこれらの混合物を用いることができる。また、ラジ
カル重合性でない一価エボキシ化合物としては、n−ブ
チルグリシジルエーテルなどのアルキルグリシジルエー
テル、フェニルグリシジルエーテルなどのアリールグリ
シジルエーテル、スチレンオキサイド、プロピレンオキ
サイド、オクチレンオキサイドなどのアルキレンオキサ
イド、三級カルボン酸グリシジルエステルなどをあげる
ことができる。A non-radically polymerizable monohydric alcohol and/or monohydric epoxy compound can also be used in combination with the above-mentioned radically polymerizable monohydric alcohol and/or monohydric epoxy compound. Such monohydric alcohols that are not radically polymerizable include aliphatic monohydric alcohols such as methanol, ethanol, propyl alcohol, butanol, benzyl alcohol, aromatic alcohols such as alkylene oxide adducts of phenol and alkylphenols,
Alicyclic alcohols such as cyclohexanol or mixtures thereof can be used. In addition, monovalent epoxy compounds that are not radically polymerizable include alkyl glycidyl ethers such as n-butyl glycidyl ether, aryl glycidyl ethers such as phenyl glycidyl ether, alkylene oxides such as styrene oxide, propylene oxide, and octylene oxide, and tertiary carbon Examples include acid glycidyl esters.
上記共重合物の無水マレイン酸および無水イタコン酸成
分1モルに対して2反応されるラジカル重合性の一価ア
ルコールおよび(または)一価エポキシ化合物、および
必要に応じてラジカル重合性でない一価アルコールおよ
び(または)一価エポキシ化合物の割合が0.05モル
未満の場合には、露光後、未露光部分の弱アルカリ水溶
液への溶解性が低くなるとともに、露光部分のハンダメ
ッキ耐性が低くなり。2 radically polymerizable monohydric alcohols and/or monohydric epoxy compounds reacted with 1 mol of the maleic anhydride and itaconic anhydride components of the above copolymer, and if necessary, a non-radically polymerizable monohydric alcohol. And/or when the proportion of the monovalent epoxy compound is less than 0.05 mol, the solubility of the unexposed part in a weak alkaline aqueous solution becomes low after exposure, and the solder plating resistance of the exposed part becomes low.
0.95モルを超える場合には、露光部分のハンダメッ
キ耐性が低くなる。When the amount exceeds 0.95 mol, the solder plating resistance of the exposed portion becomes low.
本発明においてエポキシ化合物(B)としては。In the present invention, the epoxy compound (B) includes:
トリグリシジルイソシアヌレート(TG I G) 、
ハイドロキノンジクリシジルエーテル、ビスフェノール
Sジグリシジルエーテル、タレゾールノボラック型エポ
キシ樹脂およびフェノールノボラック型エポキシ樹脂か
ら選ばれる1種または2種以上が用いられるが、TGI
Cを主成分とするものが特に貯蔵安定性が高く、このよ
うなものを用いることが最も好ましい、上記のようなタ
レゾールノボラック型エポキシ樹脂の代表例としては「
エピクロンN−695」 (大日本インキ化学工業■製
、商品名)があり。Triglycidyl isocyanurate (TG I G),
One or more selected from hydroquinone dicrycidyl ether, bisphenol S diglycidyl ether, Talezol novolac type epoxy resin, and phenol novolac type epoxy resin is used, but TGI
Those containing C as a main component have particularly high storage stability, and it is most preferable to use such resins. Typical examples of the above Talesol novolac type epoxy resins include:
"Epicron N-695" (manufactured by Dainippon Ink & Chemicals, trade name).
フェノールノボラック型エポキシ樹脂の代表例としては
「エピクロンN−775J (大日本インキ化学工業
■製、商品名)がある他、このようなノボラック型エポ
キシ樹脂としては、[エピコート152J。A typical example of a phenol novolac type epoxy resin is "Epicron N-775J (manufactured by Dainippon Ink & Chemicals, trade name)".
「エピコート154J (油化シェルエポキシ■製)
rDEN431j、rDEN438J (ダウ・ケミ
カル社製)、rEPN1138J (チバ社製)(い
ずれも商品名)などがある。"Epicoat 154J (made by Yuka Shell Epoxy ■)"
Examples include rDEN431j, rDEN438J (manufactured by Dow Chemical Company), and rEPN1138J (manufactured by Ciba Corporation) (all trade names).
エステル化物(A)に対するエポキシ化合物(B)の量
には、特に制限はないが、エステル化物(A)の無水マ
レイン酸および無水イタコン酸成分に対して、エポキシ
化合物(B)を当量比0.5〜1゜5の割合で、特に好
ましくは当量比1.0前後の割合で用いることが好まし
い。エポキシ化合物(B)を当量比0.5未満、または
1.5を趙えて用いる場合には、ハンダメッキ耐性が若
干低くなる傾向がある。There is no particular restriction on the amount of the epoxy compound (B) relative to the esterified product (A), but the equivalent ratio of the epoxy compound (B) to the maleic anhydride and itaconic anhydride components of the esterified product (A) is 0. It is preferable to use them at a ratio of 5 to 1.5, particularly preferably at an equivalent ratio of around 1.0. When the epoxy compound (B) is used at an equivalent ratio of less than 0.5 or more than 1.5, the solder plating resistance tends to be slightly lowered.
また、上記共重合物に反応させるラジカル重合性の一価
アルコールおよび(または)一価エポキシ化合物の量が
多い場合には、エポキシ化合物(B)の量を少なくする
ことができる。Furthermore, when the amount of the radically polymerizable monohydric alcohol and/or monohydric epoxy compound to be reacted with the copolymer is large, the amount of the epoxy compound (B) can be reduced.
本発明において前記(A)以外のエポキシ基を有さない
ラジカル重合性化合物(C)としては、エチル(メタ)
アクリレ−ロブチル(メタ)アクリレート、2−ヒドロ
キシエチル(メタ)アクリレート。In the present invention, as the radically polymerizable compound (C) having no epoxy group other than the above (A), ethyl (meth)
Acrylebutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate.
2−ヒドロキシプロピル(メタ)アクリレート、スチレ
ン、α−アルキルスチレン、オリゴエステル(メタ)モ
ノアクリレート (メタ)アクリル酸などのモノ (メ
タ)アクリレート類、エチレングリコールジ(メタ)ア
クリレート、ポリエチレングリコールジアクリレート、
ネオペンチルグリコールジ(メタ)アクリレート、テト
ラメチロールメタンジ(メタ)アクリレート、トリメチ
ロールプロパントリ (メタ)アクリレート、トリメチ
ロールメタントリ (メタ)アクリレート、ペンタエリ
スリトールトリ (メタ)アクリレート、ジペンタエリ
スリトールペンタ(メタ)アクリレート、ジペンタエリ
スリトールヘキサ(メタ)アクリレート、2−ヒドロキ
シ−1−(メタ)アクリロキシ−3−(メタ)アクリロ
キシプロパン、ポリエステルポリ (メタ)アクリレー
ト、ポリウレタンポリ (メタ)アクリレートなどのポ
リ (メタ)アクリレート類、ジアリルフタレート類な
ど、あるいはこれらの混合物を用いることができるが、
&1iil箔回路への接着性の面からは水酸基やカルボ
キシル基を有するものを主成分とするものを用いること
が好ましく、銅箔回路への接着性、硬化性および可塑性
の面からはテトラメチロールメタントリアクリレートを
主成分とするものを用いることが好ましい。Mono (meth)acrylates such as 2-hydroxypropyl (meth)acrylate, styrene, α-alkylstyrene, oligoester (meth)monoacrylate (meth)acrylic acid, ethylene glycol di(meth)acrylate, polyethylene glycol diacrylate,
Neopentyl glycol di(meth)acrylate, tetramethylolmethane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolmethane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate ) acrylate, dipentaerythritol hexa(meth)acrylate, 2-hydroxy-1-(meth)acryloxy-3-(meth)acryloxypropane, polyester poly(meth)acrylate, polyurethane poly(meth)acrylate, etc. ) Acrylates, diallylphthalates, etc., or mixtures thereof can be used,
From the viewpoint of adhesion to copper foil circuits, it is preferable to use materials containing hydroxyl or carboxyl groups as the main component, and from the viewpoint of adhesion to copper foil circuits, curing properties, and plasticity, tetramethylolmethanetris is preferred. It is preferable to use a material containing acrylate as a main component.
(A)および(B)からなる混合物100重量部に対し
て(C)は10〜200重量部用いられる。10 to 200 parts by weight of (C) is used per 100 parts by weight of the mixture consisting of (A) and (B).
(C)の量が10重量部未満では硬化が不十分となり、
露光後2弱アルカリ水溶液による現像の際に露光部分が
剥離し、200重量部を超えると、タックが強くなり、
マスクが貼りついてしまい、接触露光ができなくなる。If the amount of (C) is less than 10 parts by weight, curing will be insufficient,
After exposure, the exposed area peels off during development with a weakly alkaline aqueous solution, and if the amount exceeds 200 parts by weight, the tack becomes strong.
The mask will stick and contact exposure will no longer be possible.
本発明において、粘度調整などの目的で、必要に応じて
有機溶剤(D)を用いることができる。有機溶剤(D)
は、エポキシ化合物(B)の種類により適宜選択される
。このような有機溶剤(D)としては9例えば、エチレ
ングリコールモノアルキルエーテル類、ジエチレングリ
コールモノアルキルエーテル類、エチレングリコールジ
アルキルエーテル類。In the present invention, an organic solvent (D) can be used as necessary for purposes such as viscosity adjustment. Organic solvent (D)
is appropriately selected depending on the type of epoxy compound (B). Examples of such organic solvents (D) include ethylene glycol monoalkyl ethers, diethylene glycol monoalkyl ethers, and ethylene glycol dialkyl ethers.
ジエチレングリコールジアルキルエーテル類、エチレン
グリコールモノアルキルエーテルアセテート類。Diethylene glycol dialkyl ethers, ethylene glycol monoalkyl ether acetates.
ジエチレングリコールモノアルキルエーテルアセテート
類などの他、エポキシ化合物(B)が、トリグリシジル
イソシアヌレート、ハイドロキノンジグリシジルエーテ
ルまたはビスフェノールSグリシジルエーテルである場
合には、アセトン、メチルエチルケトン、メチルイソブ
チルケトンなどのケトン類。In addition to diethylene glycol monoalkyl ether acetates, when the epoxy compound (B) is triglycidyl isocyanurate, hydroquinone diglycidyl ether, or bisphenol S glycidyl ether, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone.
酢酸エチル、酢酸ブチル、酢酸イソプロピルなどのエス
テル類、トルエン、キシレンなどの芳香族炭化水素類、
ジメチルホルムアミドなどを用いることができる。Esters such as ethyl acetate, butyl acetate, isopropyl acetate, aromatic hydrocarbons such as toluene and xylene,
Dimethylformamide and the like can be used.
本発明の液状フォトソルダーレジスト組成物には。The liquid photosolder resist composition of the present invention includes:
その性能を阻害しない範囲で、必要に応じて、印刷塗布
状態を確認しやすくするためのフタロシアニングリーン
、チタン白などの染顔料、流動性を調整するための微粉
シリカなどのチクソトロープ剤、流動性を調整し現像を
容易にするためのタルク、炭酸マグネシウム、炭酸カル
シウム、天然マイカ、合成マイカなどの体質顔料、暗反
応を防止し貯蔵安定性を増大させるための重合禁止剤、
ワックス類、あるいは熱重合開始剤などの添加剤(E)
を添加することができる。上記合成マイカとしては、天
然マイカの結晶水をふっ素で置換した形の合成マイカで
あるコロイド性含ふっ素けい酸マグネシウム「ダイモナ
イト」シリーズ(トビーエ業側製、商品名)などを用い
ることが好ましい。また、露光に用いられる放射線が紫
外線の場合には、硬化性の面から、光重合開始剤および
必要に応じて光重合促進剤(F)を添加することが好ま
しい。このような光重合開始剤としては、ベンゾフェノ
ン、メチルベンゾフェノン、0−ヘンソイル安息香fi
、ベンゾイルエチルエーテル。As necessary, dyes and pigments such as phthalocyanine green and titanium white may be added to make it easier to check the printing application state, thixotropic agents such as finely divided silica to adjust fluidity, and fluidity may be added to the extent that does not impede its performance. extender pigments such as talc, magnesium carbonate, calcium carbonate, natural mica, and synthetic mica to adjust and facilitate development; polymerization inhibitors to prevent dark reactions and increase storage stability;
Additives (E) such as waxes or thermal polymerization initiators
can be added. As the synthetic mica, it is preferable to use colloidal fluorine-containing magnesium silicate "Dimonite" series (manufactured by Tobie Industries, trade name), which is a synthetic mica in which the water of crystallization of natural mica is replaced with fluorine. Further, when the radiation used for exposure is ultraviolet rays, from the viewpoint of curability, it is preferable to add a photopolymerization initiator and, if necessary, a photopolymerization accelerator (F). Examples of such photopolymerization initiators include benzophenone, methylbenzophenone, and 0-hensoylbenzoin.
, benzoylethyl ether.
2.2−ジエトキシアセトフヱノン、2.4−ジエチル
チオキサントンなどがあり、光重合促進剤としてはp−
ジメチル安息香酸イソアミル、4.4−ビス(ジエチル
アミノ)ベンゾフェノン、ジメチルエタノールアミンな
どがある。Examples of photopolymerization accelerators include 2,2-diethoxyacetophenone and 2,4-diethylthioxanthone.
Examples include isoamyl dimethylbenzoate, 4,4-bis(diethylamino)benzophenone, and dimethylethanolamine.
上記(A)、 (B)および(C)、必要に応じて(
D)、 (E)および(F)が混合され、三本ロール
、ボールミルなどの分散手段、あるいはスーパーミキサ
ーなどの攪拌手段により混練または混合される。このよ
うに混練または混合して得られた液状フォトソルダーレ
ジスト組成物は、スクリーン印刷。(A), (B) and (C) above, as necessary (
D), (E) and (F) are mixed and kneaded or mixed using a dispersing means such as a triple roll or a ball mill, or a stirring means such as a super mixer. The liquid photo solder resist composition obtained by kneading or mixing in this manner is used for screen printing.
ロールコート、カーテンフローコート、スプレーコート
などの方法により、銅箔回路上全面に印刷塗布される。Printing is applied to the entire surface of the copper foil circuit using methods such as roll coating, curtain flow coating, and spray coating.
印刷塗布後、必要に応じて遠赤外線または温風により5
0〜80℃程度にプリベークされ有機溶剤(D)が除去
され、ハンダメッキされる部分だけが放射線を通さない
ようにしたネガマスクを用いて放射線による露光が行な
われる。ネガマスクとしては、放射線が紫外線の場合に
はネガフィルムが。After printing and applying, if necessary, use far infrared rays or warm air to
The organic solvent (D) is removed by prebaking at about 0 to 80° C., and exposure to radiation is performed using a negative mask that does not allow radiation to pass through only the portion to be soldered. Negative film is used as a negative mask when the radiation is ultraviolet rays.
電子線の場合には金属製マスクが、X線の場合には鉛製
°マスクが、それぞれ使用されるが9M便なネガフィル
ムが使用できるため放射線としては紫外線を用いること
が好ましい。紫外線の強度としては700〜600mJ
/−である。次に、炭酸ナトリウム水溶液などの弱アル
カリ性の現像液によりスプレーなどの手段で現像され、
150〜170℃程度の熱風で1時間程度あるいは赤外
線で170〜180℃に7〜8分程度ボスト−ベークさ
れ、ハンダメッキ耐性を有するソルダーレジスト基板を
得られる。In the case of electron beams, metal masks are used, and in the case of X-rays, lead masks are used, but it is preferable to use ultraviolet rays as the radiation because 9M negative film can be used. The intensity of ultraviolet rays is 700 to 600 mJ
/-. Next, it is developed by means such as spraying with a weakly alkaline developer such as an aqueous sodium carbonate solution.
A solder resist substrate having solder plating resistance can be obtained by boss-baking with hot air at about 150 to 170° C. for about 1 hour or with infrared rays at 170 to 180° C. for about 7 to 8 minutes.
(実施例)
以下、実施例により本発明を説明する。例中1部とは重
量部を1%とは重量%をそれぞれ表わす。(Example) The present invention will be explained below with reference to Examples. In the examples, 1 part means part by weight, and 1% means % by weight.
合成例1
スチレン−無水マレイン酸共重合体rsMA1000J
(ARCO社製、商品名、無水マレイン酸含有率5
0モル%)404部をジエチレングリコールジメチルエ
ーテル(以下、ジグライムという。)425部に加熱溶
解したものに、空気を吹き込みながら、2−ヒドロキシ
エチルアクリレート(以下2−HEAという。)46.
4部を滴下し、110℃で18時間加熱反応させた後、
80℃にまで冷却し、エタノール50部を滴下し、さら
に80℃で8時間加熱反応させた。得られたエステル化
物溶液(a)は。Synthesis Example 1 Styrene-maleic anhydride copolymer rsMA1000J
(manufactured by ARCO, trade name, maleic anhydride content 5
404 parts of 2-hydroxyethyl acrylate (hereinafter referred to as 2-HEA) was heated and dissolved in 425 parts of diethylene glycol dimethyl ether (hereinafter referred to as diglyme) while blowing air.
After dropping 4 parts and reacting by heating at 110°C for 18 hours,
The mixture was cooled to 80°C, 50 parts of ethanol was added dropwise, and the reaction mixture was heated at 80°C for 8 hours. The obtained esterified product solution (a) is.
固形分54%、酸価160の粘稠褐色液体であった。It was a viscous brown liquid with a solid content of 54% and an acid value of 160.
合成例2
rsMAloooJ 404部をジグライム500部に
加熱溶解したものに、空気を吹き込みながら。Synthesis Example 2 404 parts of rsMAloooJ was heated and dissolved in 500 parts of diglyme while blowing air.
2−HEA50部を滴下し、110℃で18時間反応さ
せた。得られたエステル化物溶液(b)は、固形分50
%、酸価165の褐色の粘稠液体であった。50 parts of 2-HEA was added dropwise and reacted at 110°C for 18 hours. The obtained esterified product solution (b) had a solid content of 50
It was a brown viscous liquid with an acid value of 165% and an acid value of 165.
合成例3
90℃に加熱したジグライム400部に、スチレン90
部、メチルメタアクリレート60部、無水マレイン酸1
50部、アゾビスイソブチロニトリル3部およびイソオ
クチルメルカプトプロピオネート3部を30分間で滴下
した後、ちっ素気流中にて90℃で2時間反応させた。Synthesis Example 3 Add 90 parts of styrene to 400 parts of diglyme heated to 90°C.
parts, 60 parts of methyl methacrylate, 1 part of maleic anhydride
50 parts of azobisisobutyronitrile and 3 parts of isooctylmercaptopropionate were added dropwise over 30 minutes, and the mixture was reacted at 90° C. for 2 hours in a nitrogen stream.
次に、このようにして得られたスチレン−メチルメタア
クリレート−無水マレイン酸共重合体溶液に2−HEA
100部を滴下し。Next, 2-HEA was added to the styrene-methyl methacrylate-maleic anhydride copolymer solution thus obtained.
Drop 100 parts.
100℃で18時間反応させた後、80℃にまで冷却し
、トルエンジイソシアネート20部を加え、80℃で2
時間加熱して未反応の2−HEAとトルエンジイソシア
ネートとを反応させた。次に、テトラメチロールメタン
トリアクリレート20部を滴下し。After reacting at 100°C for 18 hours, it was cooled to 80°C, 20 parts of toluene diisocyanate was added, and the mixture was reacted at 80°C for 2 hours.
The mixture was heated for a period of time to cause unreacted 2-HEA to react with toluene diisocyanate. Next, 20 parts of tetramethylolmethane triacrylate was added dropwise.
80℃で2時間加熱して未反応のトルエンジイソシアネ
ートとテトラメチロールメタントリアクリレートの一部
とを反応させた。得られたエステル化物溶液(C)は、
固形分52%、エステル化物含有率46.3%、酸価1
52の褐色粘稠液体であった。The mixture was heated at 80° C. for 2 hours to cause unreacted toluene diisocyanate to react with a portion of tetramethylolmethane triacrylate. The obtained esterified product solution (C) is
Solid content 52%, ester content 46.3%, acid value 1
52 brown viscous liquid.
合成例4
90℃に加熱したジグライム430部に、スチレン90
部、メチルメタアクリレート50部、無水マレイン酸1
50部、アゾビスイソブチロニトリル3部およびイソオ
クチルメルカプトプロピオネート3部を30分間で滴下
し、ちっ素気流中、90℃で2時間反応させた後、2−
ヒドロキシエチルメタアクリレート156部を滴下し、
空気を吹き込みながら100℃で20分間反応させた。Synthesis Example 4 90 parts of styrene was added to 430 parts of diglyme heated to 90°C.
parts, 50 parts of methyl methacrylate, 1 part of maleic anhydride
50 parts of azobisisobutyronitrile and 3 parts of isooctylmercaptopropionate were added dropwise over 30 minutes, and after reacting at 90°C for 2 hours in a nitrogen stream, 2-
Add 156 parts of hydroxyethyl methacrylate dropwise,
The reaction was carried out at 100° C. for 20 minutes while blowing air.
得られたエステル化物溶液(d)は、固形分51%、酸
価132の褐色粘稠液体であった。The obtained esterified product solution (d) was a brown viscous liquid with a solid content of 51% and an acid value of 132.
合成例5
スチレン−無水マレイン酸共重合体く無水マレイン酸含
有率12.5モル%2分子量3600)860部をブチ
ルセロソルブアセテート942部に溶解したものを10
0℃に加熱し、これに2−HEA116部を滴下し、空
気を吹き込みながら100℃で18時間反応させた。得
られたエステル化物溶液(e)は、固形分50%、酸価
120の粘稠液体であった。Synthesis Example 5 Styrene-maleic anhydride copolymer (Moleic anhydride content: 12.5 mol%, molecular weight: 3,600) 860 parts dissolved in 942 parts of butyl cellosolve acetate was prepared by dissolving 10
The mixture was heated to 0°C, 116 parts of 2-HEA was added dropwise thereto, and the mixture was reacted at 100°C for 18 hours while blowing air. The obtained esterified product solution (e) was a viscous liquid with a solid content of 50% and an acid value of 120.
合成例6
rsMAloooJ 404部をジグライム400部に
溶解したものに、グリシジルメタアクリレート113.
6部を滴下し、酸素気流中、80℃で6時間反応させた
。得られたエステル化物溶液(f)は。Synthesis Example 6 To a solution of 404 parts of rsMAloooJ in 400 parts of diglyme, 113.0 parts of glycidyl methacrylate was added.
6 parts were added dropwise, and the mixture was reacted at 80° C. for 6 hours in an oxygen stream. The obtained esterified product solution (f) is.
固形分57%、酸価188の粘稠液体であった。It was a viscous liquid with a solid content of 57% and an acid value of 188.
比較合成例
rsMAloooJ 404部をジグライム400部に
溶解したものに、エタノール92部を滴下し。Comparative Synthesis Example 92 parts of ethanol was added dropwise to a solution of 404 parts of rsMAloooJ in 400 parts of diglyme.
80℃で18時間反応させた。得られたエステル化溶液
(g)は、固形分55%、酸価154の褐色粘稠液体で
あった。The reaction was carried out at 80°C for 18 hours. The obtained esterification solution (g) was a brown viscous liquid with a solid content of 55% and an acid value of 154.
実施例1〜6および比較例1〜5
表1に示す組成の合成例1〜6および比較合成例で得ら
れたエステル化物溶液(a)〜(g)、エポキシ化合物
(B)およびラジカル重合性化合物(C)の混合物10
0部に、2.4−ジエチルチオキサントン2.0部、p
−ジメチル安息香酸イソアミル0.5部、フタロシアニ
ングリーン1.2部、微粉シリカ1.2部、タルク12
部を加え、三本ロールで混練し、液状フォトソルダーレ
ジスト組成物を得た。得られた液状フォトソルダーレジ
スト組成物の貯蔵安定性を試験した結果をあわせて表1
に示す。結果は。Examples 1 to 6 and Comparative Examples 1 to 5 Esterified product solutions (a) to (g) obtained in Synthesis Examples 1 to 6 and Comparative Synthesis Examples with the compositions shown in Table 1, epoxy compound (B), and radical polymerizability Mixture 10 of compound (C)
0 parts, 2.0 parts of 2.4-diethylthioxanthone, p
-0.5 parts of isoamyl dimethylbenzoate, 1.2 parts of phthalocyanine green, 1.2 parts of finely divided silica, 12 parts of talc
and kneaded with three rolls to obtain a liquid photo solder resist composition. Table 1 also shows the results of testing the storage stability of the obtained liquid photosolder resist composition.
Shown below. Result is.
ゲル化までの時間で表示した。It was expressed as the time until gelation.
得られた液状フォトソルダーレジスト組成物を。The obtained liquid photo solder resist composition.
150メツシユのポリエステル製スクリーン版を用いて
、w44部エポキシ−ガラス繊維積層板上全面にスクリ
ーン印刷し、80℃で30分間プリベークした後、試験
用ネガフィルム「フジステップガイド215段ステップ
」 (富士写真フィルム■製、商品名)を接触させ、高
圧水銀灯により、露光強度13゜5 m W / ct
l 、露光量700mJ/aJで紫外線露光した。露光
後、1.5%炭酸ナトリウム水溶液(液温30℃)を用
いてスプレー圧3 kH/ cdで20秒間現像した。Screen printing was performed on the entire surface of the W44 epoxy-glass fiber laminate using a 150-mesh polyester screen plate, and after pre-baking at 80°C for 30 minutes, a test negative film "Fuji Step Guide 215 Step" (Fuji Photo) was applied. (trade name) made of film (trade name) was brought into contact with a high-pressure mercury lamp at an exposure intensity of 13°5 mW/ct.
1, and was exposed to ultraviolet light at an exposure dose of 700 mJ/aJ. After exposure, development was performed using a 1.5% aqueous sodium carbonate solution (liquid temperature: 30°C) at a spray pressure of 3 kHz/cd for 20 seconds.
露光現像後の残りステップ段数をあわせて表1に示す。Table 1 also shows the number of steps remaining after exposure and development.
現像後、150℃で1時間ポストベークを行なった。ボ
ストベーク後、フランクスrLONCOレジンフラック
ス77−25J (LONCO社製、商品名)を塗布
し、80℃で2分間乾燥し、1分間空冷し、260±5
℃のハンダ浴に20秒間浸漬し、空冷した後、1.1.
1−1−リクロルエタンで洗浄した後、セロファン粘着
テープ基盤目剥離試験により密着性の評価を行なった。After development, post-baking was performed at 150°C for 1 hour. After boiling, apply Franks rLONCO Resin Flux 77-25J (manufactured by LONCO, trade name), dry at 80℃ for 2 minutes, air cool for 1 minute,
After immersion in a solder bath at ℃ for 20 seconds and air cooling, 1.1.
After washing with 1-1-lichloroethane, adhesion was evaluated by a cellophane adhesive tape substrate peel test.
これを1回目として、続いて2回目以降のハンダ浴浸漬
からセロファン粘着テープ基盤目剥離試験までのサイク
ルをくりかえした。結果をあわせて表1に示す。This was the first time, and the cycle from second and subsequent immersion in the solder bath to the cellophane adhesive tape substrate peeling test was repeated. The results are also shown in Table 1.
なお1表1中、略号は次の通りである。In Table 1, the abbreviations are as follows.
HQDGE :ハイドロキノンジグリシジルエーテルB
PSDGE:ビスフェノールSジグリシジルエーテル
エピコー)828 :ビスフェノールA型エポキシ樹脂
(油化シェルエポキシ■製、商品名)TMPTAニトリ
メチロールプロパントリアクリレート
TMMTA :テトラメチロールメタントリアクリレー
ト
TEC;DA :テトラエチレングリコールジアクリレ
ート
(以下、余白)
〔発明の効果〕
本発明により、貯蔵安定性にすぐれ一液型としても使用
可能で1弱アルカリ水溶液で現像することができ9作業
環境保全や大気汚染の問題がなく、露光現像後にすぐれ
たハンダメッキ耐性を発現する液状フォトソルダーレジ
スト組成物が得られるようになった。HQDGE: Hydroquinone diglycidyl ether B
PSDGE: Bisphenol S diglycidyl ether Epicor) 828: Bisphenol A type epoxy resin (manufactured by Yuka Shell Epoxy ■, trade name) TMPTA nitrimethylolpropane triacrylate TMMTA: Tetramethylolmethane triacrylate TEC; DA: Tetraethylene glycol diacrylate (Hereinafter, blank spaces) [Effects of the Invention] The present invention has excellent storage stability, can be used as a one-component type, and can be developed with a weakly alkaline aqueous solution. A liquid photosolder resist composition that exhibits excellent solder plating resistance after development can now be obtained.
Claims (1)
ル%以上と無水マレイン酸および無水イタコン酸以外の
ラジカル重合性モノマー90モル%以下とを共重合して
得られる共重合物の無水マレイン酸および無水イタコン
酸成分1モルに対して、ラジカル重合性の一価アルコー
ルおよび(または)一価エポキシ化合物、および必要に
応じてラジカル重合性でない一価アルコールおよび(ま
たは)一価エポキシ化合物0.05〜0.95モルの割
合で反応させて得られるエステル化物(A)、およびト
リグリシジルイソシアヌレート、ハイドロキノンジグリ
シジルエーテル、ビスフェノールSジグリシジルエーテ
ル、クレゾールノボラック型エポキシ樹脂およびフェノ
ールノボラック型エポキシ樹脂から選ばれる1種または
2種以上のエポキシ化合物(B)からなる混合物100
重量部、前記(A)以外のエポキシ基を有さないラジカ
ル重合性化合物(C)10〜200重量部、および必要
に応じて有機溶剤(D)からなる液状フォトソルダーレ
ジスト組成物。Maleic anhydride and itaconic anhydride, which are copolymers obtained by copolymerizing 10 mol% or more of maleic anhydride and/or itaconic anhydride with 90 mol% or less of a radically polymerizable monomer other than maleic anhydride and itaconic anhydride. For one mol of acid components, the amount of alcoholic alcohol of radical polymerization, (or) perimed epoxy compounds, and unrealistic alcohol, and (or) perimed epoxy compounds, which are not radical polarization, as needed. Esterified product (A) obtained by reacting at a ratio of 95 moles, and one or more selected from triglycidyl isocyanurate, hydroquinone diglycidyl ether, bisphenol S diglycidyl ether, cresol novolac type epoxy resin, and phenol novolac type epoxy resin Mixture 100 consisting of two or more epoxy compounds (B)
A liquid photosolder resist composition comprising: parts by weight, 10 to 200 parts by weight of a radically polymerizable compound (C) having no epoxy group other than the above (A), and, if necessary, an organic solvent (D).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62037847A JPH0833656B2 (en) | 1987-02-23 | 1987-02-23 | Liquid photo solder resist composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62037847A JPH0833656B2 (en) | 1987-02-23 | 1987-02-23 | Liquid photo solder resist composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63205649A true JPS63205649A (en) | 1988-08-25 |
JPH0833656B2 JPH0833656B2 (en) | 1996-03-29 |
Family
ID=12508928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62037847A Expired - Lifetime JPH0833656B2 (en) | 1987-02-23 | 1987-02-23 | Liquid photo solder resist composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0833656B2 (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03137648A (en) * | 1989-10-24 | 1991-06-12 | Tokyo Ohka Kogyo Co Ltd | Heat-resistant photosensitive resin composition |
US5723261A (en) * | 1989-11-30 | 1998-03-03 | Tamura Kaken Co., Ltd. | Photopolymerizable composition |
JP2007079294A (en) * | 2005-09-15 | 2007-03-29 | Sanyo Chem Ind Ltd | Photosensitive resin composition |
JP2007133032A (en) * | 2005-11-08 | 2007-05-31 | Sanyo Chem Ind Ltd | Photosensitive resin composition |
JP2016075912A (en) * | 2015-10-20 | 2016-05-12 | 株式会社タムラ製作所 | Photosensitive resin composition, and production method of printed wiring board and reflection sheet having cured coating of photosensitive resin composition |
JP5997860B1 (en) * | 2016-03-16 | 2016-09-28 | 互応化学工業株式会社 | Liquid solder resist composition and printed wiring board |
JP6154942B1 (en) * | 2016-07-11 | 2017-06-28 | 互応化学工業株式会社 | Liquid solder resist composition and printed wiring board |
JP2017167336A (en) * | 2016-03-16 | 2017-09-21 | 互応化学工業株式会社 | Liquid solder resist composition and printed wiring board |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62285903A (en) * | 1986-06-04 | 1987-12-11 | Ube Ind Ltd | Photocurable composition |
JPS6311930A (en) * | 1986-07-03 | 1988-01-19 | Mitsui Toatsu Chem Inc | Photosensitive resin composition |
-
1987
- 1987-02-23 JP JP62037847A patent/JPH0833656B2/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62285903A (en) * | 1986-06-04 | 1987-12-11 | Ube Ind Ltd | Photocurable composition |
JPS6311930A (en) * | 1986-07-03 | 1988-01-19 | Mitsui Toatsu Chem Inc | Photosensitive resin composition |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03137648A (en) * | 1989-10-24 | 1991-06-12 | Tokyo Ohka Kogyo Co Ltd | Heat-resistant photosensitive resin composition |
US5723261A (en) * | 1989-11-30 | 1998-03-03 | Tamura Kaken Co., Ltd. | Photopolymerizable composition |
JP2007079294A (en) * | 2005-09-15 | 2007-03-29 | Sanyo Chem Ind Ltd | Photosensitive resin composition |
JP2007133032A (en) * | 2005-11-08 | 2007-05-31 | Sanyo Chem Ind Ltd | Photosensitive resin composition |
JP4672527B2 (en) * | 2005-11-08 | 2011-04-20 | 三洋化成工業株式会社 | Photosensitive resin composition |
JP2016075912A (en) * | 2015-10-20 | 2016-05-12 | 株式会社タムラ製作所 | Photosensitive resin composition, and production method of printed wiring board and reflection sheet having cured coating of photosensitive resin composition |
JP5997860B1 (en) * | 2016-03-16 | 2016-09-28 | 互応化学工業株式会社 | Liquid solder resist composition and printed wiring board |
JP2017167336A (en) * | 2016-03-16 | 2017-09-21 | 互応化学工業株式会社 | Liquid solder resist composition and printed wiring board |
WO2017158660A1 (en) * | 2016-03-16 | 2017-09-21 | 互応化学工業株式会社 | Liquid solder resist composition and printed circuit board |
CN107533294A (en) * | 2016-03-16 | 2018-01-02 | 互应化学工业株式会社 | Liquid solder mask agent composition and printed substrate |
US20180136559A1 (en) * | 2016-03-16 | 2018-05-17 | Goo Chemical Co., Ltd. | Liquid solder resist composition and printed wiring board |
US10254647B2 (en) | 2016-03-16 | 2019-04-09 | Goo Chemical Co., Ltd. | Liquid solder resist composition and printed wiring board |
US10261414B2 (en) | 2016-03-16 | 2019-04-16 | Goo Chemical Co., Ltd. | Liquid solder resist composition and printed wiring board |
JP6154942B1 (en) * | 2016-07-11 | 2017-06-28 | 互応化学工業株式会社 | Liquid solder resist composition and printed wiring board |
JP2017167505A (en) * | 2016-07-11 | 2017-09-21 | 互応化学工業株式会社 | Liquid solder resist composition and printed wiring board |
Also Published As
Publication number | Publication date |
---|---|
JPH0833656B2 (en) | 1996-03-29 |
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